Chem, Volume 4
Supplemental Information
Macrocyclic Polyradicaloids with Unusual
Super-ring Structure and Global Aromaticity
Chunchen Liu, María Eugenia Sandoval-Salinas, Yongseok Hong, Tullimilli Y.Gopalakrishna, Hoa Phan, Naoki Aratani, Tun Seng Herng, Jun Ding, HirokoYamada, Dongho Kim, David Casanova, and Jishan Wu
S1
Supplementary Information for
Macrocyclic Polyradicaloids with Unusual Super-ring
Structure and Global Aromaticity
Chunchen Liu, María Eugenia Sandoval-Salinas, Yongseok Hong, Tullimilli Y.
Gopalakrishna, Hoa Phan, Naoki Aratani, Tun Seng Herng, Jun Ding, Hiroko Yamada,
Dongho Kim,* David Casanova* and Jishan Wu*
Correspondence to: [email protected] (J.W.); [email protected] (D.C.);
[email protected] (D.K.)
Table of Contents
1. Materials and methods∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S2
1.1. General experimental methods∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S2
1.2 Synthetic procedure and characterization data∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S3
1.3 Additional spectra and figures∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S5
2. Theoretical calculations∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S23
3. X-ray crystallographic data ∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S39
4. Additional NMR and mass spectra of intermediate compounds∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S43
5. References∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙∙S49
6. Appendix: Cartesian coordinates of the optimized geometry………………………..S51
S2
1. Materials and methods
1.1. General experimental methods
All reagents and catalysts were obtained from the commercial suppliers and used
without further purification. Anhydrous dichloromethane (DCM) and toluene were
obtained from solvent purification systems from LC Technology Solutions Inc. Anhydrous
tetrahydrofuran (THF) was freshly distilled over sodium/benzophenone prior to use. 2-
Mesitylmagnesium bromide (1M in THF) was purchased from Sigma-Aldrich. The 1H
NMR and 13C NMR spectra were obtained on Bruker DPX 300/500 NMR spectrometer
with tetramethylsilane (TMS) as internal standard. MALDI-TOF mass spectra (MS) were
obtained on a Bruker Autoflex instrument with dithranol or tetracyanoquinodimethane
(TCNQ) as matrix. High-resolution (HR) APCI and ESI mass spectra were recorded on a
Bruker amazon X mass spectrometer. UV-vis-NIR absorption spectra were obtained on a
Shimadzu UV-3600 plus spectrometer. The electrochemical measurements (cyclic
voltammetry (CV) and differential pulse voltammetry (DPV)) were conducted in
anhydrous DCM with 0.1 M tetra-n-butyammoniumhexafluorophosphate (n-Bu4NPF6) as
supporting electrolyte at room temperature under inert atmosphere. A gold stick, a platinum
wire and Ag/AgCl (3M KCl solution) were used as working electrode, counter electrode
and reference electrode, respectively. The potential was externally calibrated against the
ferrocene/ferrocenium (Fc/Fc+) couple. Continuous wave X-band ESR spectra were
measured on a JEOL (FA200) spectrometer.
A Quantum Design 7 Telsa superconducting quantum interference device
magnetometer (SQUID-VSM) was used for the magnetic measurements. Solid sample of
compound with a weight of 8-10 mg was sealed in a plastic capsule. Considering the
stability of the compound, the magnetic susceptibility was measured in the temperature
range from 2 K to 300 K with an applied field of 0.5 T. After correction of diamagnetic
contributions from the sample, using tabulated constants, sample holder and paramagnetic
contamination the magnetic data were fitted with the following equation:
𝜒𝑇 = 𝑁𝑔2𝛽2
𝑘∗
𝐴
𝐵
For such a complicated polyradicaloid system, we cannot simply apply Bleaney-Bowers
equation to fit the data. Alternatively, the data was fitted by considering the relative energy
between each spin states (calculated by RAS-SF method, Figure S19).
For 8MC-M:
A = 2exp((-26.93x)/(kT)) + 2exp((-32.33x)/(kT)) + 2exp((-32.37x)/(kT)) + 2exp((-
49.08x)/(kT)) + 2exp((-49.14x)/(kT)) + 2exp((-56.65x)/(kT)) + 2exp((-32.37x)/(kT)) +
2exp((-57.23x)/(kT)) + 8exp((-52.49x)/(kT)) + 8exp((-69.84x)/(kT)) + 8exp((-71.64x)/(kT))
+ 8exp((-72.76x)/(kT)) + 8exp((-75.57x)/(kT))
B =1 + exp((-34.64x)/(kT)) + exp((-43.37x)/(kT)) + exp((-48.58x)/(kT)) + 2exp((-
51.2x)/(kT)) + 3exp((-26.93x)/(kT)) + 3exp((-32.33x)/(kT)) + 3exp((-32.37x)/(kT)) +
3exp((-49.08x)/(kT)) + 3exp((-49.14x)/(kT)) + 3exp((-56.65x)/(kT)) + 3exp((-
32.37x)/(kT)) + 3exp((-57.23x)/(kT)) + 5exp((-52.49x)/(kT)) + 5exp((-69.84x)/(kT)) +
5exp((-71.64x)/(kT)) + 5exp((-72.76x)/(kT)) + 5exp((-75.57x)/(kT))
For 10MC-M:
S3
A = 2 + 2exp((-9.67x)/(kT)) + 2exp((-10.35x)/(kT)) + 2exp((-20.87x)/(kT)) + 2exp((-
25.59x)/(kT)) + 8exp((-15.24x)/(kT)) + 8exp((-27.78x)/(kT)) + 8exp((-29.73x)/(kT)) +
20exp((-67.37x)/(kT)) + 20exp((-89.43x)/(kT))
B = 3 + exp((-4.14x)/(kT)) + exp((-10.88x)/(kT)) + exp((-26.74x)/(kT)) + exp((-
28.65x)/(kT)) + exp((-37.50x)/(kT)) + 3exp((-9.67x)/(kT)) + 3exp((-10.35x)/(kT)) +
3exp((-20.87x)/(kT)) + 3exp((-25.59x)/(kT)) + 5exp((-15.24x)/(kT)) + 5exp((-
27.78x)/(kT)) + 5exp((-29.73x)/(kT)) + 5exp((-39.34x)/(kT)) + 7exp((-67.36x)/(kT))
The femtosecond time-resolved transient absorption (fs-TA) spectrometer consists of an
optical parametric amplifier (OPA; Palitra, Quantronix) pumped by a Ti: sapphire
regenerative amplifier system (Integra-C, Quantronix) operating at 1 kHz repetition rate
and an optical detection system. The generated OPA pulses have a pulse width of ~100 fs
and an average power of 1 mW in the range of 280-2700 nm, which are used as pump
pulses. White light continuum (WLC) probe pulses were generated using a sapphire
window (3 mm thick) by focusing a small portion of the fundamental 800 nm pulses, which
was picked off by a quartz plate before entering the OPA. The time delay between pump
and probe beams was carefully controlled by making the pump beam travel along a variable
optical delay (ILS250, Newport). Intensities of the spectrally dispersed WLC probe pulses
are monitored by a High Speed Spectrometer (Ultrafast Systems) for both visible and near-
infrared measurements. To obtain the time-resolved transient absorption difference signal
(ΔA) at a specific time, the pump pulses were chopped at 500 Hz and absorption spectra
intensities were saved alternately with or without pump pulse. Typically, 4000 pulses
excite the samples to obtain the fs-TA spectra at each delay time. The polarization angle
between pump and probe beam was set at the magic angle (54.7o) using a Glan-laser
polarizer with a half-wave retarder in order to prevent polarization-dependent signals.
Cross-correlation fwhm in pump-probe experiments was less than 200 fs and chirp of WLC
probe pulses was measured to be 800 fs in the 400-800 nm region. To minimize chirp, all
reflection optics in the probe beam path and a quartz cell of 2 mm path length were used.
After fs-TA experiments, the absorption spectra of all compounds were carefully examined
to detect if there were artifacts due to degradation and photo-oxidation of samples. The
three-dimensional data sets of ΔA versus time and wavelength were subjected to singular
value decomposition and global fitting to obtain the kinetic time constants and their
associated spectra using Surface Xplorer software (Ultrafast Systems).
1.2. Synthetic procedure and characterization data
Compounds 8MC-CHO and 10MC-CHO. A three-necked round bottom flask was
charged with 4,6-dibromobenzene-1,3-dicarbaldehyde 1 (300 mg, 1.03 mmol) and 1,3-
benzenediboronic acid 2 (170.4 mg, 1.03 mmol), NaHCO3(6.9 g, 82.4 mmol, in 15 mL
water), tetrahydrofuran (400 mL) and purged with argon for 30 mins. Pd2(dba)3(94.2 mg,
0.1 mmol) and tri-tert-butylphosphoniumtetrafluoroborate ([(t-Bu)3PH]BF4) (119.4 mg,
0.41 mmol) were added subsequently under argon. The resultant mixture was degassed by
three freeze-pump-thaw cycles and then heated at 85 oC for 3 days. After cooling to room
temperature, the THF was evaporated and water was added in the reaction mixture. After
extraction of the reaction mixture with chloroform followed by drying over sodium sulfate,
the solvent was evaporated to dryness. The desired 8MC-CHO and 10MC-CHO can be
S4
observed from the MALDI-TOF mass spectrum of the obtained crude products as shown
in Figure S2. The crude mixture was first passed through a silica gel column (chloroform)
followed by a Recycling Preparative Gel Permeation Chromatography purification (GPC,
from Japan Analytical Industry Co., Ltd.). Pure 8MC-CHO and 10MC-CHO were
successfully isolated in 24% and 10% yield, respectively. The structures of both were also
confirmed by X-ray crystallographic analysis of single crystals grown from THF/methanol
(see later part for details).
8MC-CHO: 1H NMR (CDCl3, 500 MHz): δ ppm 10.11 (s, 8H), 8.60 (s, 4H), 7.63 (t, J =
4.6 Hz, 8H), 7.59 (s, 4H), 7.55 (d, J = 1.8 Hz, 4H), 7.53 (s, 4H). 13C NMR (CDCl3, 125
MHz): δ ppm 190.22, 148.50, 137.91, 134.08, 133.55, 130.82, 129.54, 128.73, 29.86.
HRMS (APCI, m/z): [(M+H)+] calcd for C56H32O8, 833.2172; found, 833.2170.
10MC-CHO: 1H NMR (CDCl3, 400 MHz): δ ppm 10.04 (s, 10H), 8.55 (s, 5H), 7.63 (t, J
= 8.3 Hz, 5H), 7.52 (dd, 3J = 7.3 Hz, 4J = 1.7 Hz, 10H), 7.50 (s, 5H), 7.47 (d, J = 4.86 Hz,
5H). 13C NMR (CDCl3, 100 MHz): δ ppm 190.14, 148.15, 137.40, 133.41, 130.51, 130.06,
129.67, 128.96, 29.69. HRMS (APCI, m/z): [(M+H)+] calcd for C70H40O10, 1040.2625;
found, 1040.2627.
Compounds 8MC-H and 10MC-H. Compound 8MC-CHO (10 mg, 0.012 mmol) or
10MC-CHO (10 mg, 0.01 mmol) was dissolved in 10 mL of anhydrous THF under argon
atmosphere. 2-Mesitylmagnesium bromide (1M solution in THF, 80 equivalents for 8MC-
CHO and 100 equivalents for 10MC-CHO) was added dropwise into the solution. After
12 hours, the reaction was quenched with water, and extracted with diethyl ester. After
drying the combined organic phase over sodium sulfate, the solvents were then removed
to afford the crude alcohol product 8MC-OH or 10MC-OH. Without further purification,
these two compounds were dissolved in 20 mL of dry DCM treated with 0.5 mL of
BF3.Et2O. The reaction color changed immediately, and the products 8MC-H and 10MC-
H with fluorescence were generated. After three hours, the reaction was quenched with
water. The mixture was extracted with DCM followed by dried over anhydrous sodium
sulfate. After solvent was removed and the residue was purified with silica gel column
chromatography (Hexane: DCM = 3: 2, v/v) to afford 8MC-H and 10MC-H as white solids
in 57% and 63% yield, respectively. The structures of both compounds were confirmed by
HR MS (Figure S3 and Figure S4) and 2D 1H-1H NOESY NMR measurements (Figure S5
and Figure S6). The purity was further confirmed by recycling analytical GPC (Figures S7-
S8).
8MC-H. 1H NMR (CD2Cl2, 400 MHz): δ ppm 8.95-8.78 (m, 8H), 6.90 (s, 16H), 6.73-6.40
(m, 8H), 5.78-54 (m, 8H), 2.54-2.47 (m, 24H), 2.21-2.07 (m, 24H), 1.76 (s, 8H), 1.28 (s,
8H), 0.70-0.50 (m, 8H). 13C NMR (CD2Cl2, 100 MHz): δ ppm 148.60, 141.39, 138.37,
138.02, 136.71, 134.15, 130.89, 129.07, 120.86, 122.12, 51.48, 21.98, 21.79, 20.93. HRMS
(APCI, m/z): [(M+H)+] calcd for C128H113, 1649.8837; found, 1649.8854.
10MC-H. 1H NMR (CD2Cl2, 400 MHz): δ ppm 8.62 (s, 10H), 6.88 (t, J = 11.6 Hz, 20H),
6.47 (s, 10H), 5.61-5.39 (m, 10H), 2.64-2.43 (m, 30H), 2.14 (s, 30H), 1.18-1.02 (m,
30H).13C NMR (CD2Cl2, 100 MHz): δ ppm 147.54, 140.21, 137.79, 137.37, 136.22,
134.19, 130.25, 128.73, 119.84, 119.49, 111.24, 111.06. HRMS (APCI, m/z): [(M+H)+]
calcd for C160H140, 2061.0950; found, 2061.0947.
Compounds 8MC-M and 10MC-M. 8MC-H (15 mg, 0.0091 mmol) or 10MC-H (15 mg,
0.0073 mmol) was dissolved in 15 mL of anhydrous DCM under argon atmosphere. 2,3-
S5
Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (8 equivalents for 8MC-H, 10 equivalents
for 10MC-H) was added to the solution in portion and the progress of the reaction was
monitored by MALDI-TOF mass spectra (Figures S9-S10). For both reactions, the color
changed quickly from colorless to dark green (8MC-M) and dark blue (10MC-M). After
reacting for 45 mins (for 8MC-M) or 15 mins (for 10MC-M), the solvent was removed
under vacuum. The crude product was purified by flash column chromatography (10%
trimethylamine deactivated silica gel, DCM as the eluent) followed by precipitation into
acetonitrile to afford the final products of 8MC-M and 10MC-M in nearly quantitative
yield. The purity was further confirmed by recycling analytical GPC (Figures S13-S14).
8MC-M. This compound is reasonably stable at ambient air and light condition in both
solution and in solid state. The structure of 8MC-M was confirmed by HR MS (Figure
S11), VT 1H NMR spectrum (Figure 2A, full range spectrum in Figure S15, and relative
integral intensity in Figures S16-17), 2D 1H-1H ROESY NMR spectrum (Figure S18), and
a preliminary X-ray crystallographic analysis (Figure S19). 1H NMR (THF-d8, 233 K, 500
MHz): δ ppm 11.37 (s, proton “a”), 6.85 (m, proton “c”), 1.28 (s, proton “e”), 0.87 (s,
proton “d”), -12.08 (s, proton “b”). The signals for protons “a-c” are very weak due to
exchange with the thermally populated triplet species, which limits the 2D NOESY NMR
analysis as we all as 13C NMR spectral measurement. HR MS [APCI, m/z (z =1), [(M+H)+]
calculated for C128H104, 1640.8133; found, 1640.8124.
10MC-M. This compound is reasonably stable at ambient air and light condition in both
solution and in solid state. The 1H NMR spectrum of 10MC-M was significantly broadened
due to its triplet ground state and only broadened resonances for methyl groups can be
observed at various temperatures. Its structure was confirmed by HR MS (Figure S12) and
preliminary X-ray crystallographic analysis (Figure S20). HR MS [ESI, m/z (z=2),
(M+H)+] calculated for C160H130, 1025.5081; found, 1025.5083.
1.3. Additional spectra and figures
Figure S1. Four and the only four possible resonance structures of 8MC and 10MC in
their closed-shell forms.
S6
Figure S2. MALDI-TOF mass spectrum for the reaction mixture of Suzuki coupling
reaction mediated macrocyclization. In addition to the [4+4] (8MC-CHO, m/z = 832.4
g/mol) and [5+5] (10MC-CHO, m/z = 1040.5 g/mol) products, the [3+3] (m/z = 624.1
g/mol) and [6+6] (m/z = 1248.7 g/mol) products were also detected. However, they could
not be isolated by recycling GPC.
Figure S3. HR-APCI [m/z (z = 1), (M+1)+] mass spectrum of 8MC-H.
S7
Figure S4. HR-APCI [m/z (z = 1), (M+1)+] mass spectrum of 10MC-H.
S8
Figure S5. 1H-1H NOESY NMR spectrum of 8MC-H in CD2Cl2 (500 MHz). Due to the
existence of various isomers and the bowl-shaped structure, all the protons were split into
multiple peaks. The assignment was based on the through space interaction between the
neighboring protons. The integration was in agreement with the theoretical prediction.
ad
b cf e g g g
g
g
gef
c
bd
a
d, e
d, f c, f
d, f d, eb, e
c, f
S9
Figure S6. 1H-1H NOESY NMR spectrum of 10MC-H in CD2Cl2 (500 MHz). Due to the
existence of various isomers, some of the protons were split into multiple peaks. The
assignment was based on the through space interaction between the neighboring protons.
The integration was in agreement with the theoretical prediction.
ad
b ce f g
g
fe
c
b
d
a
d, f
d, e
c, d
c, e
c, d
c, e
d, e d, f
b, f
S10
Figure S7. Recycling GPC curves of 8MC-H in the first 14 cycles. Shimazu GPC column
K802 (8.0mm id x 30cm), SPD-20AV UV-Vis spectrophotometric detector (210 nm), and
chloroform as eluent.
Figure S8. Recycling GPC curves of 10MC-H in the first 13 cycles. Shimazu GPC column
K802 (8.0mm id x 30cm), SPD-20AV UV-Vis spectrophotometric detector (red: 210 nm;
blue: 280 nm), and chloroform as eluent.
S11
Figure S9. Oxidative dehydrogenation process for 8MC-H (a) and 10MC-H (b) monitored
by MALDI-TOF MS after addition of DDQ in anhydrous DCM. They were fully converted
to final products 8MC-M and 10MC-M in 45 and 15 minutes, respectively.
Figure S10. MALDI-TOF mass spectra of 8MC-M (a) and 10MC-M (b). Inset is a
comparison between calculated and observed isotopic distributions.
1640 1650
0
50
100
150
200
250
300
Inte
ns
ity
(a
.u.)
m/z
1635 1640 1645 1650 16550
100
200
300
400
500
Inte
ns
ity
(a
.u.)
m/z
1640 1650
0
200
400
600
800
1000
1200
Inte
ns
ity
(a
.u.)
m/z
2040 2050 2060 2070
0
200
400
600
800
1000
Inte
ns
ity
(a
.u.)
m/z
2040 2045 2050 2055 2060 2065 2070
0
50
100
150
200
250
Inte
ns
ity
(a
.u.)
m/z
1648.1
1649.11650.1
1651.1
1652.1
1642.91641.9
1640.9
1643.8
1644.81645.91646.8
1647.81649.9
1640.8
1649.9
1641.8
1642.8
1643.8
1644.8
2059.5
2060.5
2061.5
2062.5
2063.5
2064.5
2052.1
2051.1
2053.1
2054.1
2055.1
2056.1
10MC-H
10MC-M
8MC-H
8MC-M
15 min
45 min 15 min
(a) (b)
1639.9
500 1000 1500 2000
0
200
400
600
800
Inte
nsity (
a.u
.)
m/z
8MC-M
1000 1500 2000 2500
0
200
400
Inte
nsity (
a.u
.)
m/z
10MC-M
1640 1645 1650 1655m/z
observed
calculated
2050 2055 2060 2065m/z
observed
calculated
(a) (b)
1641.80 2052.11
S12
Figure S11. HR-APCI [m/z (z = 1), (M+1)+] mass spectrum of 8MC-M.
Figure S12. HR-ESI [m/z (z = 2), (M+H)+] mass spectrum of 10MC-M.
S13
Figure S13. Recycling GPC curves of 8MC-M in the first 3 cycles. Shimazu GPC column
K802 (8.0mm id x 30cm), SPD-20AV UV-Vis spectrophotometric detector (blue: 280 nm;
green: 350 nm; orange: 400 nm), and chloroform as eluent.
Figure S14. Recycling GPC curves of 10MC-M in the first 3 cycles. Shimazu GPC column
K802 (8.0mm id x 30cm), SPD-20AV UV-Vis spectrophotometric detector (red: 210 nm;
green: 350 nm; orange: 400 nm), and chloroform as eluent.
S14
Figure S15. Full-range 1H NMR spectrum of 8MC-M in THF-d8 at 233 K. The signals for
protons “a”-“c” are very weak due to exchange with thermally populated triplet species
and thus these signals are magnified. The stars indicate the residue solvent peaks.
Figure S16. The relative integral intensity of protons “a” and “b” in the 1H NMR
spectrum of 8MC-M at 233 K.
a
ab
b
c
c
H2O
e
*
* *d
S15
Figure S17. The relative integrals of protons “e” and “d” in 1H NMR spectrum of 8MC-
M at 233 K, showing a nearly 2: 1 ratio. The stars indicate the residue solvent peaks.
edH2O
**
S16
Figure S18. 2D 1H-1H ROESY NMR spectrum of 8MC-M in THF-d8 at 233 K. (A) Full-
range spectrum; (B) magnified narrow-range spectrum showing the interaction between
protons “c” with protons “d” and “e”; (C) magnified narrow-range spectrum showing the
interaction between protons “a” with protons “e”.
S17
Figure S19. X-ray crystallographic structure (left: top-view; right: side-view) of 8MC-M.
The backbone is clearly confirmed and shows a bowl-shaped geometry, in agreement with
DFT calculation. However, due to the low quality of the data (weak diffraction and
existence of disordered solvents), we could not do bond length analysis.
Figure S20. X-ray crystallographic structure (left: top-view; right: side-view) of 10MC-
M. The backbone is clearly confirmed and nearly planar, in agreement with DFT
calculation. However, due to the low quality of the data (weak diffraction and existence of
disordered solvents), we could not do bond length analysis.
S18
Figure S21. (a) Optimized (UB3LYP/6-31G(d,p)) geometry of 8MC-M in the singlet
diradical ground state with atom labels (see Cartesian coordinates in Appendix). (b)
Calculated (restricted) 1H NMR spectrum (B3LYP/6-31G(d,p)-GIAO) based on the
optimized geometry. (c) Chemical structure and labeling of 8MC-M, with the bowl
pointing from the inner hub to the outer rim through the paper. Protons e and c point to the
concave side, while protons e’ and c’ point to the convex side. Calculations predict that
proton a will appear at very low field (δ = +13.0 ppm), while proton b will appear in very
high field (δ = -20.2 ppm), which is in agreement with the experimental observation (Figure
2A in the main manuscript). At the same time, all the protons e and c at the concave side
will appear at the higher field than those (e’, c’) at the convex side due to the shielding/de-
shielding effect. It should be pointed out that the calculation was based on the single
optimized geometry and the chemical shifts for the protons on the mesityl groups are very
sensitive to the geometry and local environment and what we measured are the averaged
peaks. So the most useful information from this calculation is the relative position of the
protons “a” and “b”, rather than the absolute values.
S19
We also optimized 8MC-M at the (restricted and unrestricted) KMLYP/6-31G(d,p) level
of theory. Based on the optimized geometries (see Cartesian coordinates in Appendix),
relative 1H chemical shifts were calculated as:
𝛿𝑐𝑎𝑙𝑐𝑥 = 𝜎𝑟𝑒𝑓 − 𝜎𝑥
where 𝜎𝑟𝑒𝑓 and 𝜎𝑥 are the NMR isotropic magnetic shielding values for the reference
(TMS) and the X proton of 8MC-M, respectively, calculated at (restricted) KMLYP/6-
311+G(2d,p)-GIAO method. In agreement with previous results, i.e. experimental and
B3LYP calculations, a and b protons appear at very low (δ = 14.80 – 14.78 ppm) and very
high field (δ = -24.06 - -24.10 ppm), respectively (Figures S22-S23 and Table S1).
Figure S22. Calculated 1H NMR spectrum of 8MC-M by KMLYP/6-31G(d,p)-GIAO
method obtained for the (restricted) KMLYP/6-31G(d,p) geometry.
Figure S23. Calculated 1H NMR spectrum of 8MC-M by KMLYP/6-31G(d,p)-GIAO
method obtained for the (unrestricted) KMLYP/6-31G(d,p) geometry.
S20
Table S1. Relative 1H shifts (in ppm) for 8MC-M computed at the (restricted) KMLYP/6-
31G(d,p)-GIAO level for the geometries optimized at the restricted and unrestricted
KMLYP/6-31G(d,p) level. Proton labels correspond to Figure S21 (c). Displacements for
d, e and e’ are given as an averaged single value. 𝜎𝑇𝑀𝑆 = 31.12 𝑝𝑝𝑚.
proton (U)KMLYP (R)KMLYP Experiment
a 11.75 14.36 11.73
b -18.60 -22.74 -12.46
c 6.11 6.63
c’ 7.98 9.01
d 1.94 1.75 3.23
e -2.69 -4.43 1.27
e’ 5.18 5.64 0.89
Figure S24. Bond labels employed in the comparison between restricted/unrestricted
KMLYP/6-31G(d,p) geometries (Table S2).
Table S2. Comparison between structural parameters of 8MC-M obtained at the restricted
and unrestricted KMLYP/6-31G(d,p) computational level. All distances are in Angstroms.
Bond labels are indicated in Figures S24.
bond (R)KMLYP (U)KMLYP
A 1.422 1.410
B 1.408 1.389
C 1.460 1.438
D 1.424 1.404
E 1.388 1.370
S21
The validity of the employed basis set 6-31G(d,p) in the computation of proton relative
shifts has been tested by comparing the results with the larger basis set 6-311+G(2d,p)
(Figure S25). The results indicate no major differences with the values obtained with 6-
31G(d,p).
Figure S25. Calculated 1H NMR spectrum of 8MC-M by KMLYP/6-311+G(2d,p)-GIAO
method obtained for the (restricted) KMLYP/6-31G(d,p) geometry.
Calculations of relative 1H shifts have been done with Gaussian 09 rev D.01. The KMLYP
functional is requested with the following keyword combination:
BLYP IOp(3/76=1000005570) IOp(3/77=0000004430) IOp(3/78=0448010000)
S22
Figure S26. VT ESR spectra of 8MC-M (a) and 10MC-M (b) in DCM (173K to118 K).
Figure S27. Measured (dot) and fitted (red plot) χMT-T curve in the SQUID measurement
for the powder of 10MC-M.
327 328 329 330 331-200
-150
-100
-50
0
50
100
150
200
Inte
nsit
y
Field (mT)
-100 oC
-110 oC
-120 oC
-130 oC
-140 oC
-150 oC
-155 oC
326 327 328 329 330 331-4000
-3000
-2000
-1000
0
1000
2000
3000
4000
Inte
nsit
y
Field (mT)
-100 oC
-110 oC
-120 oC
-130 oC
-140 oC
-150 oC
-155 oC
173 K
163 K
153 K
143 K
133 K
123 K
118 K
173 K
163 K
153 K
143 K
133 K
123 K
118 K
S23
Figure S28. Transient absorption spectra for 8MC-M (a) and 10MC-M (c) recorded in
toluene and decay profiles for 8MC-M (b) and 10MC-M (d).
2. Theoretical calculations
All computational results presented have been obtained for a molecular model where
the mesityl substituents are replaced by hydrogen substituents (8MC and 10MC). The
perpendicular disposition of the side aryl rings with respect to macrocycle suggests that
they have a minor impact in the electronic structure properties and justifies not considering
them in the computational modeling. Molecular geometries have been obtained at the
UB3LYP/6-31G(d,p) level with Gaussian 09 package1. The radical nature of the electronic
ground state and transition energies to higher states were calculated using the restricted
active space spin-flip method (RAS-SF) with Q-Chem 4.3 package2. In 8MC (10MC) we
used a spin 9-et (11-et) ROHF configuration as reference, with 8 (10) electrons in 8 (10)
orbitals as the RAS2 space and a quadruple (quintuple) spin-flip excitation operator. The
radical character degree of the ground state singlet was estimated by the number of
unpaired electrons (NU) according to equation 1, where {ni} are the natural occupation
numbers from the one-particle density matrix3-4.
i
iU nabsN )1(1 (1)
The calculated occupation numbers of HONO-i and LUNO+i (i = 0, 1, 2) can be used
as the multiple radical character indices yi calculated by using equation 25:
𝑦𝑖 =1
2(2 − 𝑛𝐻𝑂𝑁𝑂−𝑖 + 𝑛𝐿𝑈𝑁𝑂+𝑖) (2)
450 600 750 900 1050 1200 1350
-4
-3
-2
-1
0
1
8MC-M in toluene
mA
Wavelength (nm)
Time / ps
-0.5
0.3
0.4
0.5
0.6
1.0
3.0
5.0
10.0
20.0
25.0
450 600 750 900 1050 1200 1350
-15
-10
-5
0
5
m
A
Wavelength (nm)
Time / ps
-0.5
0.3
0.4
0.5
0.6
1.0
2.0
5.0
10.0
20.0
25.0
10MC-M in toluene
0 5 10 15 20 25 30 35 40
-25
-20
-15
-10
-5
0
m
A
Time / ps
pump = 700 nm
probe = 600 nm
= 0.3 and 8 ps
0 5 10 15 20 25 30 35 40
-20
-15
-10
-5
0
m
ATime / ps
pump = 700 nm
probe = 700 nm
= 0.2 and 6 ps
S24
NICS values were calculated using the standard GIAO (GIAO=NMR)6 at the level of
(U)B3LYP/6-31G(d,p). To obtain best NICS aromaticity index for 8MC and 10MC,
NICSzz values were selected.7 The iso-chemical shielding surface (ICSS)8-10 calculations
were carried out to analyze two-dimensional nucleus induced chemical shifts (2D-NICSzz)
depending on various planes. Plotting the ICSS having same scale allows us to compare
the aromaticity between the singlet and triplet state of 8MC and 10MC. Anisotropy of the
induced current density (ACID) plots (iso-value = 0.04) were calculated at (U)B3LYP/6-
31G(d,p) level by using the method developed by Herges.11 To devoid σ-bond effect, the
additional option (NMR=CSGT, IOp(10/93) = 2) was used to read in wanted p-orbitals.
The p-orbitals were classified with the analysis of molecular orbital (MO) calculations
using the optimized structures of 8MC and 10MC in the singlet and triplet state.
Our calculations show that the lowest state for the 8MC corresponds to a spin singlet
with C8v symmetry (Figure S26), although C2v and C4v singlets are computed at practically
the same energy. The lowest 10MC state is a spin triplet with D2h symmetry (Figure S26).
It is worth noting that the ring tension in 8MC strongly suppresses molecular planarity
favoring Cnv molecular symmetries. The bowl-to-bowl inversion barrier of 8MC via S-
shaped TS (Ci symmetry) was found at 29.3 kcal/mol (Figure S27). Frequency calculations
for the S-shaped structure confirms that it indeed corresponds to a critical point on the
potential energy surface of 8MC, with a vibrational mode with an imaginary frequency,
(freq = 47.5i cm-1) and a very flat mode (freq ~ 0), corresponding to symmetric and
antisymmetric vibrations out of the “molecular plane”, connecting S-shape with the C8v
(minimum) and D8h (planar) geometries, respectively. The planar structure lies at 31.5
kcal/mol with respect to the minimum (C8v) geometry (Figure S27).
Both molecules exhibit a fairly large amount of electronic states within a rather small
energy gap with respect to the electronic ground state (Figure S28 and Table S1). The
natural orbitals and occupancies for the lowest states of 8MC and 10MC molecules, i.e.
spin singlet and triplet, respectively are shown in Figure S30 and Figure S31, respectively,
and some indices quantifying the radical character are shown in Table S2.
Both 1H NMR measurements and ACID calculations of 8MC indicate that the ground
state singlet exhibits global aromaticity. Moreover, ACID and current plots (Figure 3A in
the main manuscript and Figure S33) indicate that such aromaticity can be understood or
approximated as the sum of two clockwise currents on each annulene ring (in and out). On
the other hand, the two annulene rings hold 4n electrons (24 πe, 32 πe), hence in the ground
state singlet we would expect counter-clockwise ring currents. Therefore, we consider two
alternative electronic structures as the source for global aromaticity in 8MC (ground state
singlet): (1) One annulene gives two electrons to the other one (Hückel's rule); (2) each
annulene holds a "triplet" (diradical) character (Baird's rule).
To identify which is the most plausible explanation we perform constrained DFT (C-
DFT) calculations by imposing restrictions in the inner and outer annulene rings of 8MC.
The idea is to use energy arguments to quantify the relative stability of these different
conformations and identify which might be contributing to the ground state wave function.
We call them diabatic states in the sense that they are well characterized by the charge/spin
S25
within each of the two annulenes. The "true" (adiabatic) lowest singlet (or triplet) state is
expected to be a combination of the lowest diabatic states.
The relative energies in Figure S32 for the 8MC singlet indicate that SS, TT, 1+/1- and
1-/1+ are much lower in energy than the 2-/2+ and 2+/2- states and it is unlikely that the
dianion/dication density-constrained states participate to the ground state wave function.
Hence, our calculations point towards option 2: the global aromaticity of the singlet ground
state of 8MC can be seen due to the "triplet(in)-triplet(out)" (or diradical-diradical)
character of the ground state, that is two triplets coupled as a singlet. These results can be
rationalized due to the large polyradical character in 8MC and to the diradicaloid character
in each in/out annulenes. This result is in agreement with the number of unpaired electrons
computed at the RAS-SF level (NU = 4.85 in Table S2) and with ACID calculations for the
entire molecule and for the in/out models (Figure 3A in main manuscript), and corresponds
to the application of Baird's rule to the inner and outer annulenes.
Similarly, we can rationalize that the aromaticity in 8MC triplet corresponds to mainly
having a singlet (in)-triplet(out) state (ST), which is lower in energy than the TS
configuration (Figure S32). The inner ring is anti-aromatic (Hückel’s rule) while the outer
ring is aromatic (Baird’s rule) (Figures S33-S34). The two states of 10MC (30 πe, 40 πe)
can be also rationalized with C-DFT calculations. Again, the 2-/2+ and 2+/2- states are
much higher in energy in both 10MC singlet and triplet states (Figure S32). The lowest
contribution in the 10MC ground state triplet is the ST state, with both the inner ring and
outer rings are aromatic, by following Hückel’s rule and Baird’s rule, respectively (Figure
3C and Figure S35). The first singlet excited state of 10MC have either TT or SS states
with close energy, and in both states, the cancelation effect of the inner ring and outer rings
(aromaticity vs. anti-aromaticity) leads to a non-aromatic character (Figure S36).
For comparison, similar calculations were conducted for the hydrogenated analogues of
8MC and 10MC, that is, 8MC-16H and 10MC-20H, in which eight and ten protons are
added to the radical centers in the cyclcopenta-ring, respectively (Figure S39A). The
calculated ACID plots and NICSzz maps (Figure S39B-E) clearly show the localized
aromatic character at each benzene ring, without any global aromaticity.
To conclude, despite the rather complicated electronic structure nature of lowest singlet
and triplet states of the two studied macrocycles, the global aromaticity in 8MC (singlet)
can be qualitatively seen as a result of some TT character in the ground state wave function,
and not from dianion/dication contributions. Similar arguments can be used for 10MC.
S26
Figure S29. Lowest conformers for 8MC (bowl-shaped) and 10MC (planar) molecules.
Figure S30. Inversion energy profile between C8v structures 8MC through a D8h planar
and a S-shape structures. Energies computed at the B3LYP/6-31G(d) level.
S27
Figure S31. Vertical excitation energies (in kcal/mol) computed at the RAS-SF/6-31G(d)
level for the lowest electronic states of 8MC (C8v) and 10MC (D2h).
S28
Table S3. A comparison of the calculated vertical excitation energies (in kcal/mol) of 8MC
and 10MC by RAS-SF/6-31G(d) and UB3LYP/6-31G(d,p) method. Spin-unrestricted DFT
energies appear slightly higher than RAS-SF results. Moreover, the strong
multiconfigurational character of 8MC and 10MC molecules advises the use of an
electronic structure approach able to deal with strong correlations. Therefore, in this case,
we consider RAS-SF energy gaps to be more reliable than the UB3LYP counterparts.
Relative
Energy
(kcal/mol)
RAS-SF/6-31G(d) UB3LYP/6-31G(d,p)
8MC 10MC 8MC 10MC
singlet S1 0.0 0.4 0 1.2
S2 3.5 1.1
S3 4.3 2.7
S4 4.8 2.9
S5 5.1 3.8
S6 5.1 -
S7 6.9 -
S8 7.6 -
S9 9.3 -
S10 9.6 -
triplet T1 2.7 0.0 3.6 3.8
T2 3.2 1.0
T3 3.2 1.0
T4 4.9 2.1
T5 4.9 2.6
T6 5.7 -
T7 5.7 -
T8 6.4 -
quintet Q1 5.2 1.5 16.2 0.0
Q2 7.0 2.8
Q3 7.2 3.0
Q4 7.3 3.9
Q5 7.6 5.2
Q6 8.4
Q7 10.1
Q8 10.5
septet SE1 11.6 6.7 23.3 16.5
SE2 12.5 8.9
SE3 12.7 12.9
nonet NON1 20.6 12.9 34.8 27.7
NON2 - 15.2
NON3 - 20.7
11-et 11-et1 - 22.8 - 50.3
S29
Figure S32. Calculated (UB3LYP/6-31G(d,p)) spin density (α spin-β spin) distribution
maps of 8MC and 10MC at their different spin states (iso-value = 0.002).
S30
Figure S33. Frontier natural orbitals and electronic occupancies for the lowest state (open-
shell singlet) of 8MC computed at the RAS-SF/6-31G(d) level.
S31
Figure S34. Frontier natural orbitals and electronic occupancies for the lowest state
(triplet) of 10MC computed at the RAS-SF/6-31G(d) level.
Table S4. Calculated radical indices yi, i = 0, 1, 2, 3, 4, number of unpaired electrons
(NU) and singlet-triplet energy gaps (ΔEST in kcal/mol) at the RAS-SF/6-31G(d) level.
8MC (C8v) 10MC (D2h)
Singlet Triplet
y0 0.79 1.00 1.00
y1 0.56 0.92 0.97
y2 0.56 0.56 0.55
y3 0.45 0.53 0.50
y4 - 0.48 0.46
NU 4.85 7.08 7.04
ΔEST -2.7 +0.4
S32
Figure S35. State energy diagram for the diabatic states of 8MC and 10MC molecules
computed with C-DFT. All energies are given with respect to the lowest singlet or triplet
state. State labels correspond to the restriction on inner/outer annulene rings, respectively.
SS: singlet-singlet, TT: triplet-triplet; 1-/1+: anion-cation; 2-/2+: dianion-dication.
S33
Figure S36. Magnified ACID plots for 8MC. (A) Magnified ACID plot for 8MC in its
singlet (TT) state. (B) Magnified ACID plot for 8MC in its first triplet (ST) excited state.
Figure S37. ACID plots and 2D NICS map. (A) ACID plots of the individual inner/outer
rings and 8MC in the first triplet excited state. (B) 2D NICSzz map of 8MC in the first
triplet excited state. The arrows along the inner/outer rings indicate a clockwise
(diamagnetic) or a counter-clockwise (paramagnetic) current flow, and the arrows in the
rings show the alignment of the frontier two or four π electrons.
8MC-singlet (TT) 8MC-triplet (ST)
8MC-out-Triplet
+
32 πe24 πe
8MC-in-Singlet
-7.5 -5.0 -2.5 0.0 2.5 5.0 7.5
-3.0
-1.5
0.0
1.5
3.0
-7.5
-5.0
-2.5
0.0
2.5
5.0
7.5
Y-a
xis
(Å
)
60.000
30.000
0.000
-30.000
-60.000
X-axis (Å)
Z-a
xis
(Å
)
+
8MC-Triplet (ST)
A B
NICSzz(0) = 9.96 ppm
S34
Figure S38. Magnified ACID plots for 10MC in its triplet ground state.
Figure S39. ACID plots and 2D NICS map. (A) ACID plots of the individual inner/outer
rings and 10MC in the first singlet excited state. (B) 2D NICSzz map of 10MC in the first
singlet excited state showing non-aromatic character. The TT and SS states have a similar
energy, and due to the cancelation effect (aromaticity vs anti-aromaticity) between the inner
and outer rings in both cases, the molecule is non-aromatic. The arrows along the
inner/outer rings indicate a clockwise (diamagnetic) or a counter-clockwise (paramagnetic)
current flow, and the arrows in the rings show the alignment of the frontier two or four π
electrons.
30 πe
+OR
10MC-out-Triplet
10MC-in-Singlet
10MC-in-Triplet
10MC-out-Singlet
SS
TT
+
+
40 πe
NICSzz(0) = -6.17 ppm
-10.0 -7.5 -5.0 -2.5 0.0 2.5 5.0 7.5 10.0
-10.0
-7.5
-5.0
-2.5
0.0
2.5
5.0
7.5
10.0
X-axis (Å)
Y-a
xis
(Å
)Z
-axis
(Å
)
-10.0 -7.5 -5.0 -2.5 0.0 2.5 5.0 7.5 10.0
-2-1012
100.000
-50.000
0.000
50.000
-100.000
+
S35
The expected contributions of individual rings (inner and outer) to the molecular
aromaticity for singlet and triplet states can be obtained following the Hückel’s and Baird’s
rules, respectively. On the other hand, there isn’t a well-established rule for aromaticity on
doublet states, i.e. rings with +1 or -1 charge. Mandado et al. suggested an “expanded
Baird’s rule” for radical systems to evaluate aromaticity as the sum of separate
contributions from α and β π-electrons, respectively.12 Following these rules, in Table S3
we estimate contributions to the aromaticity.
Table S5. Contributions to the global aromaticity from α and β π-electrons for each diabatic
state of inner (_in) and outer (_out) rings of 8MC and 10MC molecules. S = singlet (close-
sell), D = doublet, T = triplet, A = aromatic, AA = antiaromatic, NA = no aromatic
(cancelation between α and β contributions).
ring
model
spin
multiplicity
charge α-elec β-elec global
8MC_in S 0 12 (AA) 12 (AA) AA
8MC_in T 0 13 (A) 11 (A) A
8MC_in D -1 13 (A) 12 (AA) NA
8MC_in D +1 12 (AA) 11 (A) NA
8MC_in S -2 13(A) 13(A) A
8MC_in S +2 11(A) 11(A) A
8MC_out S 0 16 (AA) 16 (AA) AA
8MC_out T 0 17 (A) 15 (A) A
8MC_out D -1 17 (A) 16 (AA) NA
8MC_out D +1 16 (AA) 15 (A) NA
8MC_out S -2 17(A) 17(A) A
8MC_out S +2 15(A) 15(A) A
10MC_in S 0 15 (A) 15 (A) A
10MC_in T 0 16 (AA) 14 (AA) AA
10MC_in D -1 16 (AA) 15 (A) NA
10MC_in D +1 15 (A) 14 (AA) NA
10MC_in S -2 16(AA) 16(AA) AA
10MC_in S +2 14(AA) 14(AA) AA
10MC_out S 0 20 (AA) 20 (AA) AA
10MC_out T 0 21 (A) 19 (A) A
10MC_out D -1 21 (A) 20 (AA) NA
10MC_out D +1 20 (AA) 19 (A) NA
10MC_out S -2 21(A) 21(A) A
10MC_out S +2 19(A) 19(A) A
In order to further explore the contributions of +1/-1 and -1/+1 configurations to the global
aromaticity, we investigated the anisotropy of the current-induced density (ACID) plots of
±1 annulene inner and outer model rings. Charged (±1) inner rings of 8MC can be
classified as antiaromatic, since they holds a counter-clockwise current. While, the ACID
of ionic outer ring of 8MC seems to be disconnected, i.e., without a continuous current
flow along the ring. Inner/outer rings of 10MC show counter-clockwise (antiaromatic) and
clockwise (aromatic) current flows, respectively (Figure S37).
S36
Figure S40. ACID plots of ionic fragments of 8MC (top) and 10MC (bottom).
S37
Figure S41. Calculated bond lengths (in Å) and HOMA values of each individual rings for
8MC and 10MC in their ground state and the first excited state.
S38
Figure S42. ACID plots and 2D NICS maps of 8MC-16H and 10MC-20H. (A)
Chemical structure of 8MC-16H and 10MC-20H. ACID plots for 8MC-16H (B) and
10MC-20H (D) show localized aromaticity on each benzene ring. 2D NICSzz maps of
8MC-16H (C) and 10MC-20H (E) show no-aromatic character at the center of
macrocycles.
-7.5 -5.0 -2.5 0.0 2.5 5.0 7.5
-2
-1
0
1
2
Y-a
xis
(Å
)
-7.5
-5.0
-2.5
0.0
2.5
5.0
7.5
60.000
30.000
0.000
-30.000
-60.000
X-axis (Å)
Z-a
xis
(Å
)
-10.0 -7.5 -5.0 -2.5 0.0 2.5 5.0 7.5 10.0
-10.0
-7.5
-5.0
-2.5
0.0
2.5
5.0
7.5
10.0
X-axis (Å)
Y-a
xis
(Å
)Z
-axis
(Å
)
-10.0 -7.5 -5.0 -2.5 0.0 2.5 5.0 7.5 10.0-3-2-10123
100.000
-50.000
0.000
50.000
-100.000
NICSzz(0) = 7.11 ppm
NICSzz(0) = 5.83 ppm
S39
3. X-ray crystallographic data
Table S6. Crystallographic data and structure refinement for 8MC-CHO. CCDC
number: 1559806.
Empirical formula C66 H51 N O10
Formula weight 1018.08
Temperature 100(2) K
Wavelength 1.54178 Å
Crystal system Triclinic
Space group P-1
Unit cell dimensions a = 11.2862(5) Å a= 101.119(2)°.
b = 12.4963(5) Å b= 99.809(2)°.
c = 20.0553(8) Å g = 108.339(2)°.
Volume 2552.12(19) Å3
Z 2
Density (calculated) 1.325 Mg/m3
Absorption coefficient 0.719 mm-1
F(000) 1068
Crystal size 0.312 x 0.132 x 0.099 mm3
Theta range for data collection 2.318 to 70.067°.
Index ranges -13<=h<=13, -15<=k<=15, -23<=l<=24
Reflections collected 34654
Independent reflections 9596 [R(int) = 0.0356]
Completeness to theta = 67.679° 99.1 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.7536 and 0.6518
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 9596 / 707 / 861
S40
Goodness-of-fit on F2 1.058
Final R indices [I>2sigma(I)] R1 = 0.0700, wR2 = 0.1984
R indices (all data) R1 = 0.0768, wR2 = 0.2067
Extinction coefficient n/a
Largest diff. peak and hole 0.964 and -0.966 e.Å-3
Table S7. Crystallographic data and structure refinement for 10MC-CHO. CCDC
number: 1559833.
Empirical formula C70 H40 O10
Formula weight 1041.02
Temperature 103(2) K
Wavelength 1.54178 Å
Crystal system Monoclinic
Space group C2/m
Unit cell dimensions a = 27.067(2) Å a= 90°.
b = 23.017(2) Å b= 122.082(5)°.
c = 15.3850(12) Å g = 90°.
Volume 8121.0(12) Å3
Z 4
Density (calculated) 0.851 Mg/m3
Absorption coefficient 0.461 mm-1
F(000) 2160
Crystal size 0.111 x 0.089 x 0.060 mm3
Theta range for data collection 2.720 to 66.593°.
Index ranges -32<=h<=32, -27<=k<=26, -16<=l<=18
Reflections collected 25360
Independent reflections 7272 [R(int) = 0.1420]
Completeness to theta = 66.593° 98.5 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.7538 and 0.6005
S41
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 7272 / 0 / 367
Goodness-of-fit on F2 0.809
Final R indices [I>2sigma(I)] R1 = 0.0770, wR2 = 0.1810
R indices (all data) R1 = 0.1400, wR2 = 0.2015
Extinction coefficient n/a
Largest diff. peak and hole 0.268 and -0.228 e.Å-3
X-ray data of 8MC-M were measured at low temp of 100K with a Bruker D8 Venture
diffractometer equipped with a four circles Kappa goniometer and Photon II detector. A
monochromated Cu Kα radiation (λ = 1.54187 Å) was used for the measurement. The
structure was solved by using direct methods.13 Structure refinements were carried out by
using SHELXL-2014/7 program.14 CCDC number: 1574873 contains supplementary
crystallographic data. These data can be obtained free of charge from the Cambridge
Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
Single crystal of 8MC-M was obtained through slow diffusion of acetonitrile to the
chlorobenzene solution by layering method. The crystals were very thin long needles and
contained many severely disordered solvent molecules in the cavity. They gave only weak
diffractions at high two theta angles. However, the main skeletal structure was solved. The
contributions to the scattering arising from the presence of the disordered solvents in
the crystal were removed by use of the utility SQUEEZE in the PLATON software
package.15
Table S8. Crystallographic data and structure refinement for 8MC-M.
Empirical formula C128 H104
Formula weight 1642.11
Temperature 100(2) K
Wavelength 1.54178 Å
Crystal system Tetragonal
Space group P4/ncc
Unit cell dimensions a = 30.4484(16) Å a= 90°.
b = 30.4484(16) Å b= 90°.
c = 13.7537(8) Å g = 90°.
Volume 12751.1(15) Å3
Z 4
Density (calculated) 0.855 Mg/m3
Absorption coefficient 0.363 mm-1
F(000) 3488
Crystal size 0.596 x 0.075 x 0.044 mm3
Theta range for data collection 2.902 to 57.200°.
Index ranges -32<=h<=32, -32<=k<=33, -14<=l<=14
Reflections collected 89133
Independent reflections 4316 [R(int) = 0.2276]
Completeness to theta = 57.200° 99.5 %
Absorption correction Semi-empirical from equivalents
S42
Max. and min. transmission 0.7479 and 0.5021
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 4316 / 0 / 289
Goodness-of-fit on F2 1.490
Final R indices [I>2sigma(I)] R1 = 0.1656, wR2 = 0.4711
R indices (all data) R1 = 0.2761, wR2 = 0.5119
Extinction coefficient n/a
Largest diff. peak and hole 0.628 and -0.253 e.Å-3
X-ray data of 10MC-M were taken at 93K with a Rigaku XtaLAB P200 diffractometer by
using graphite monochromated Cu K radiation ( = 1.54187 Å) (We thank Professor
Atsuhiro Osuka for sharing his equipment!). The structure was solved by using direct
methods.12 Structure refinements were carried out by using SHELXL-2014/7 program.13
CCDC number: 1559835 contains supplementary crystallographic data. These data can be
obtained free of charge from the Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
Single crystal of 10MC-M was obtained through slow diffusion of acetonitrile to the
chlorobenzene solution. Since the crystals were tiny and contained many severely
disordered solvent molecules in the cavity, they gave only weak diffractions. However,
these are not significant concern for the main skeletal structure. The contributions to the
scattering arising from the presence of the disordered solvents in the crystal were removed
by use of the utility SQUEEZE in the PLATON software package.14 The carbon-carbon
bonds were appropriately restrained by DFIX, SADI and DANG instruments during
refinement.
Table S9. Crystallographic data and structure refinement for 10MC-M.
Empirical formula C160 H130
Formula weight 2052.63
Temperature 100(2) K
Wavelength 1.54187 Å
Crystal system Orthorhombic
Space group Imm2
Unit cell dimensions a = 43.12(16) Å a= 90°.
b = 8.57(3) Å b= 90°.
c = 31.30(12) Å g = 90°.
Volume 11563(70) Å3
Z 2
Density (calculated) 0.590 Mg/m3
Absorption coefficient 0.250 mm-1
F(000) 2180
Crystal size 0.100 x 0.100 x 0.010 mm3
Theta range for data collection 6.648 to 34.998°.
Index ranges -32<=h<=32, -6<=k<=6, -23<=l<=23
Reflections collected 24037
Independent reflections 2817 [R(int) = 0.2476]
S43
Completeness to theta = 34.998° 98.7 %
Absorption correction Semi-empirical from equivalents
Max. and min. transmission 0.998 and 0.975
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 2817 / 502 / 453
Goodness-of-fit on F2 0.928
Final R indices [I>2sigma(I)] R1 = 0.1195, wR2 = 0.2706
R indices (all data) R1 = 0.2013, wR2 = 0.3249
Absolute structure parameter 0.5
Extinction coefficient n/a
Largest diff. peak and hole 0.221 and -0.178 e.Å-3
4. Additional NMR and mass spectra of intermediate compounds
Figure S43. 1H NMR spectrum of 8MC-CHO in CDCl3 (500 MHz).
ab
c
de
e
f
a
b e cdf
S44
Figure S44. 13C NMR spectrum of 8MC-CHO in CDCl3 (125 MHz).
Figure S45. 1H NMR spectrum of 10MC-CHO in CDCl3 (400 MHz).
a
b
cd
e
e
f
a
bd
ecf
S45
Figure S46. 13C NMR spectrum of 10MC-CHO in CDCl3 (100 MHz).
Figure S47. 1H NMR spectrum of 8MC-H in CD2Cl2 (400 MHz).
a
d
b c
f e
ggg
a
bc
dd
ef
g
S46
Figure S48. 13C NMR spectrum of 8MC-H in CD2Cl2 (100 MHz).
Figure S49. 1H NMR spectrum of 10MC-H in CD2Cl2 (400 MHz).
feg
cbda
a
bc
dd
g
ef
S47
Figure S50. 13C NMR spectrum of 10MC-H in CD2Cl2 (100 MHz).
S48
Figure S51. HR-APCI [m/z (z = 1), (M+1)+] mass spectrum of 8MC-CHO.
Figure S52. HR-APCI [m/z (z = 1), (M+1)+] mass spectrum of 10MC-CHO.
S49
5. References
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Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji,
H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G.,
Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida,
M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery Jr., J. A.,
Peralta, J. E., Ogliaro, F., Bearpark, M. J., Heyd, J., Brothers, E. N., Kudin, K. N.,
Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A. P., Burant,
J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, N. J., Klene, M., Knox, J.
E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E.,
Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L.,
Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J.,
Dapprich, S., Daniels, A. D., Farkas, Ö., Foresman, J. B., Ortiz, J. V., Cioslowski, J. &
Fox, D. J. Gaussian 09, Gaussian, Inc., Wallingford, CT, USA, 2009.
[2] Shao, Y., Gan, Z., Epifanovsky, E., Gilbert, A. T. B., Wormit, M., Kussmann, J.,
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Jacobson, L. D., Kaliman, I., Khaliullin, R. Z., Kus, T., Landau, A., Liu, J., Proynov, E.
I., Rhee, Y. M., Richard, R. M., Rohrdanz, M. A., Steele, R. P., Sundstrom, E. J.,
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M. W. D., Harbach, P. H. P., Hauser, A. W., Hohenstein, E. G., Holden, Z. C., Jagau, T. -
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Kosenkov, D., Kowalczyk, T., Krauter, C. M., Laog, K. U., Laurent, A., Lawler, K. V.,
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P., Manzer, S. F., Mao, S. -P., Mardirossian, N., Marenich, A. V., Maurer, S. A.,
Mayhall, N. J., Oana, C. M., Olivares-Amaya, R., O’Neill, D. P., Parkhill, J. A., Perrine,
T. M., Peverati, R., Pieniazek, P. A., Prociuk, A., Rehn, D. R., Rosta, E., Russ, N. J.,
Sergueev, N., Sharada, S. M., Sharmaa, S., Small, D. W., Sodt, A., Stein, T., Stuck, D.,
Su, Y. -C., Thom, A. J. W., Tsuchimochi, T., Vogt, L., Vydrov, O., Wang, T., Watson,
M. A., Wenzel, J., White, A., Williams, C. F., Vanovschi, V., Yeganeh, S., Yost, S. R.,
You, Z. -Q., Zhang, I. Y., Zhang, X., Zhou, Y., Brooks, B. R., Chan, G. K. L., Chipman,
D. M., Cramer, C. J., Goddard III, W. A., Gordon, M. S., Hehre, W. J., Klamt, A.,
Schaefer III, H. F., Schmidt, M. W., Sherrill, C. D., Truhlar, D. G., Warshel, A., Xu, X.,
Aspuru-Guzik, A., Baer, R., Bell, A. T., Besley, N. A., Chai, J. -D., Dreuw, A., Dunietz,
B. D., Furlani, T. R., Gwaltney, S. R., Hsu, C. -P., Jung, Y., Kong, J., Lambrecht, D. S.,
Liang, W. Z., Ochsenfeld, C., Rassolov, V. A., Slipchenko, L. V., Subotnik, J. E., Van
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113, 184–215 (2015).
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density matrix. Chem. Phys. Lett. 372, 508–511.
S50
[4] Casanova, D., and Head-Gordon, M. (2009). Restricted active space spin-flip
configuration interaction approach: theory, implementation and examples. Phys. Chem.
Chem. Phys. 11, 9779–9790.
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B., Botek, E., Kubo, T., Ohta, K., and Kamada, K. (2011). (Hyper)polarizability density analysis for open-shell molecular systems based on natural orbitals and occupation numbers. Theor. Chem. Acc. 130, 711–724.
[6] Chen, Z., Wannere, C. S., Corminboeuf, C., Puchta, R., and Schleyer, P. V. R. (2005).
Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. Chem. Rev. 105,
3842–3888.
[7] Fallah-Bagher-Shaidaei, H., Wannere, S. S., Corminboeuf, C., Puchta, R., and Schleyer,
P. V. R. (2006). Which NICS aromaticity index for planar π rings is best?. Org. Lett. 8,
863–866.
[8] Klod, S., and Kleinpeter, E. (2001). Ab initio calculation of the anisotropy effect of
multiple bonds and the ring current effect of arenes—application in conformational and
configurational analysis. J. Chem. Soc., Perkin Trans. 2, 1893–1898.
[9] T. Lu, (2016). Multiwfn Software Manual, Version 3.3.9, Beijing Kein Research
Center for Natural Sciences, Beijing, China.
[10] Lu, T, and Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. J.
Comput. Chem. 33, 580–592.
[11] Geuenich, D., Hess, K., Köhler, F., and Herges, R. (2005). Anisotropy of the
induced current density (ACID), a general method to quantify and visualize electronic
delocalization. Chem. Rev. 105, 3758–3772.
[12] Mandado, M., Graña, A. M., and Pérez-Juste, I. (2008). Aromaticity in spin-
polarized systems: Can rings be simultaneously alpha aromatic and beta antiaromatic? J.
Chem. Phys. 129, 164114.
[13] SHELXT program: G. M. Sheldrick, (2015). SHELXT – Integrated space-group and
crystal-structure determination. Acta Crystallogr., Sect. A: Found. Adv. A71, 3–8.
[14] Sheldrick, G. M. (2015). Crystal structure refinement with SHELXL. Acta
Crystallogr., Sect. C: Struct. Chem. C71, 3–8.
[15] Spek, A. L. (2015). PLATON SQUEEZE: a tool for the calculation of the disordered
solvent contribution to the calculated structure factors. Acta Crystallogr., Sect. C: Struct.
Chem. C71, 9–18.
S51
6. Appendix: Cartesian coordinates of the optimized geometry
8MC (C2v)-singlet:
C 1.21051400 -5.96070100 -0.27010400
C 1.18945100 -4.73657900 0.52614900
C 0.00000000 -4.16538400 0.95788500
C -1.18945100 -4.73657900 0.52614900
C -1.21051400 -5.96070100 -0.27010400
C 0.00000000 -6.59001200 -0.62293800
C -2.55273200 -6.16744900 -0.68738200
C 2.55273200 -6.16744900 -0.68738200
C 2.50821400 -4.19185700 0.53144500
C -2.50821400 -4.19185700 0.53144500
C 3.35594100 -5.06653200 -0.26082400
C 4.65392500 -4.65392500 -0.61725100
C 5.06652900 -3.35594200 -0.26082800
C 4.19185700 -2.50821300 0.53144000
C 2.94188800 -2.94188900 0.95296700
C -2.94188800 -2.94188900 0.95296700
C -4.19185700 -2.50821300 0.53144000
C -5.06652900 -3.35594200 -0.26082800
C -4.65392500 -4.65392500 -0.61725100
C -3.35594100 -5.06653200 -0.26082400
C 5.96069800 1.21051500 -0.27011700
C 4.73657500 1.18945100 0.52614000
C 4.16538200 0.00000000 0.95787700
C 4.73657500 -1.18945100 0.52614000
C 5.96069800 -1.21051500 -0.27011700
C 6.59000900 0.00000000 -0.62295100
C 6.16744400 -2.55273000 -0.68739500
C 6.16744400 2.55273000 -0.68739500
C -1.21051400 5.96070100 -0.27010400
C -1.18945100 4.73657900 0.52614900
C 0.00000000 4.16538400 0.95788500
C 1.18945100 4.73657900 0.52614900
C 1.21051400 5.96070100 -0.27010400
C 0.00000000 6.59001200 -0.62293800
C 2.55273200 6.16744900 -0.68738200
C -2.55273200 6.16744900 -0.68738200
C -2.50821400 4.19185700 0.53144500
C 2.50821400 4.19185700 0.53144500
C -3.35594100 5.06653200 -0.26082400
C -4.65392500 4.65392500 -0.61725100
C -5.06652900 3.35594200 -0.26082800
C -4.19185700 2.50821300 0.53144000
S52
C -2.94188800 2.94188900 0.95296700
C 2.94188800 2.94188900 0.95296700
C 4.19185700 2.50821300 0.53144000
C 5.06652900 3.35594200 -0.26082800
C 4.65392500 4.65392500 -0.61725100
C 3.35594100 5.06653200 -0.26082400
C -5.96069800 -1.21051500 -0.27011700
C -4.73657500 -1.18945100 0.52614000
C -4.16538200 0.00000000 0.95787700
C -4.73657500 1.18945100 0.52614000
C -5.96069800 1.21051500 -0.27011700
C -6.59000900 0.00000000 -0.62295100
C -6.16744400 2.55273000 -0.68739500
C -6.16744400 -2.55273000 -0.68739500
H 0.00000000 -3.23300800 1.51593600
H 0.00000000 -7.48113700 -1.24527500
H 5.28247900 -5.28248100 -1.24310800
H 2.27957300 -2.27957200 1.50426800
H -2.27957300 -2.27957200 1.50426800
H -5.28247900 -5.28248100 -1.24310800
H 3.23300900 0.00000000 1.51593300
H 7.48113200 0.00000000 -1.24529000
H 0.00000000 3.23300800 1.51593600
H 0.00000000 7.48113700 -1.24527500
H -5.28247900 5.28248100 -1.24310800
H -2.27957300 2.27957200 1.50426800
H 2.27957300 2.27957200 1.50426800
H 5.28247900 5.28248100 -1.24310800
H -3.23300900 0.00000000 1.51593300
H -7.48113200 0.00000000 -1.24529000
H 2.89473900 6.98368900 -1.31343400
H -6.98368100 2.89474000 -1.31345000
H -6.98368100 -2.89474000 -1.31345000
H -2.89473900 -6.98368900 -1.31343400
H 6.98368100 -2.89474000 -1.31345000
H 6.98368100 2.89474000 -1.31345000
H -2.89473900 6.98368900 -1.31343400
H 2.89473900 -6.98368900 -1.31343400
8MC (C2v)-triplet:
C 1.20974500 -5.94876800 -0.27858100
C 1.19058500 -4.73543800 0.54044100
C 0.00000000 -4.17460800 0.98453500
C -1.19058500 -4.73543800 0.54044100
C -1.20974500 -5.94876800 -0.27858100
S53
C 0.00000000 -6.57201600 -0.64230200
C -2.54831700 -6.15193600 -0.70716200
C 2.54831700 -6.15193600 -0.70716200
C 2.50826400 -4.19450400 0.54826500
C -2.50826400 -4.19450400 0.54826500
C 3.35052100 -5.06144000 -0.26550800
C 4.64416200 -4.64415800 -0.63268500
C 5.06144200 -3.35052000 -0.26550400
C 4.19450800 -2.50826200 0.54826700
C 2.94786300 -2.94786300 0.97495800
C -2.94786300 -2.94786300 0.97495800
C -4.19450800 -2.50826200 0.54826700
C -5.06144200 -3.35052000 -0.26550400
C -4.64416200 -4.64415800 -0.63268500
C -3.35052100 -5.06144000 -0.26550800
C 5.94877300 1.20974500 -0.27858100
C 4.73543800 1.19058500 0.54044300
C 4.17461000 0.00000000 0.98453700
C 4.73543800 -1.19058500 0.54044300
C 5.94877300 -1.20974500 -0.27858100
C 6.57202000 0.00000000 -0.64230000
C 6.15194200 -2.54831400 -0.70715800
C 6.15194200 2.54831400 -0.70715800
C -1.20974500 5.94876800 -0.27858100
C -1.19058500 4.73543800 0.54044100
C 0.00000000 4.17460800 0.98453500
C 1.19058500 4.73543800 0.54044100
C 1.20974500 5.94876800 -0.27858100
C 0.00000000 6.57201600 -0.64230200
C 2.54831700 6.15193600 -0.70716200
C -2.54831700 6.15193600 -0.70716200
C -2.50826400 4.19450400 0.54826500
C 2.50826400 4.19450400 0.54826500
C -3.35052100 5.06144000 -0.26550800
C -4.64416200 4.64415800 -0.63268500
C -5.06144200 3.35052000 -0.26550400
C -4.19450800 2.50826200 0.54826700
C -2.94786300 2.94786300 0.97495800
C 2.94786300 2.94786300 0.97495800
C 4.19450800 2.50826200 0.54826700
C 5.06144200 3.35052000 -0.26550400
C 4.64416200 4.64415800 -0.63268500
C 3.35052100 5.06144000 -0.26550800
C -5.94877300 -1.20974500 -0.27858100
C -4.73543800 -1.19058500 0.54044300
C -4.17461000 0.00000000 0.98453700
S54
C -4.73543800 1.19058500 0.54044300
C -5.94877300 1.20974500 -0.27858100
C -6.57202000 0.00000000 -0.64230000
C -6.15194200 2.54831400 -0.70715800
C -6.15194200 -2.54831400 -0.70715800
H 0.00000000 -3.25157200 1.55776800
H 0.00000000 -7.45306000 -1.27908800
H 5.26524200 -5.26523700 -1.27375600
H 2.28980600 -2.28980600 1.53660700
H -2.28980600 -2.28980600 1.53660700
H -5.26524200 -5.26523700 -1.27375600
H 3.25157400 0.00000000 1.55777100
H 7.45306600 0.00000000 -1.27908400
H 0.00000000 3.25157200 1.55776800
H 0.00000000 7.45306000 -1.27908800
H -5.26524200 5.26523700 -1.27375600
H -2.28980600 2.28980600 1.53660700
H 2.28980600 2.28980600 1.53660700
H 5.26524200 5.26523700 -1.27375600
H -3.25157400 0.00000000 1.55777100
H -7.45306600 0.00000000 -1.27908400
H 2.88526500 6.95788300 -1.34905700
H -6.95788800 2.88526600 -1.34905200
H -6.95788800 -2.88526600 -1.34905200
H -2.88526500 -6.95788300 -1.34905700
H 6.95788800 -2.88526600 -1.34905200
H 6.95788800 2.88526600 -1.34905200
H -2.88526500 6.95788300 -1.34905700
H 2.88526500 -6.95788300 -1.34905700
8MC (C2v)-quintet:
C 1.20847900 -5.93642700 -0.28120600
C 1.18920200 -4.73379200 0.52933500
C 0.00000000 -4.16780600 0.96954000
C -1.18920200 -4.73379200 0.52933500
C -1.20847900 -5.93642700 -0.28120600
C 0.00000000 -6.55998000 -0.64725600
C -2.55811000 -6.14386100 -0.71056300
C 2.55811000 -6.14386100 -0.71056300
C 2.52020300 -4.18332800 0.53524000
C -2.52020300 -4.18332800 0.53524000
C 3.36250200 -5.05259300 -0.27411200
C 4.66135400 -4.64316500 -0.63151700
C 5.08119600 -3.34823400 -0.26430800
C 4.21053600 -2.50417300 0.54154700
S55
C 2.95447300 -2.94922800 0.97086100
C -2.95447300 -2.94922800 0.97086100
C -4.21053600 -2.50417300 0.54154700
C -5.08119600 -3.34823400 -0.26430800
C -4.66135400 -4.64316500 -0.63151700
C -3.36250200 -5.05259300 -0.27411200
C 5.97485200 1.21204400 -0.25661900
C 4.75526500 1.19343500 0.54838400
C 4.18248600 0.00000000 0.97267900
C 4.75526500 -1.19343500 0.54838400
C 5.97485200 -1.21204400 -0.25661900
C 6.59904400 0.00000000 -0.61532300
C 6.18332600 -2.54804400 -0.69083500
C 6.18332600 2.54804400 -0.69083500
C -1.20847900 5.93642700 -0.28120600
C -1.18920200 4.73379200 0.52933500
C 0.00000000 4.16780600 0.96954000
C 1.18920200 4.73379200 0.52933500
C 1.20847900 5.93642700 -0.28120600
C 0.00000000 6.55998000 -0.64725600
C 2.55811000 6.14386100 -0.71056300
C -2.55811000 6.14386100 -0.71056300
C -2.52020300 4.18332800 0.53524000
C 2.52020300 4.18332800 0.53524000
C -3.36250200 5.05259300 -0.27411200
C -4.66135400 4.64316500 -0.63151700
C -5.08119600 3.34823400 -0.26430800
C -4.21053600 2.50417300 0.54154700
C -2.95447300 2.94922800 0.97086100
C 2.95447300 2.94922800 0.97086100
C 4.21053600 2.50417300 0.54154700
C 5.08119600 3.34823400 -0.26430800
C 4.66135400 4.64316500 -0.63151700
C 3.36250200 5.05259300 -0.27411200
C -5.97485200 -1.21204400 -0.25661900
C -4.75526500 -1.19343500 0.54838400
C -4.18248600 0.00000000 0.97267900
C -4.75526500 1.19343500 0.54838400
C -5.97485200 1.21204400 -0.25661900
C -6.59904400 0.00000000 -0.61532300
C -6.18332600 2.54804400 -0.69083500
C -6.18332600 -2.54804400 -0.69083500
H 0.00000000 -3.24186600 1.53772500
H 0.00000000 -7.44095100 -1.28390200
H 5.28485000 -5.26917900 -1.26496700
H 2.29755200 -2.29167800 1.53383100
S56
H -2.29755200 -2.29167800 1.53383100
H -5.28485000 -5.26917900 -1.26496700
H 3.24951400 0.00000000 1.53050900
H 7.48486300 0.00000000 -1.24596900
H 0.00000000 3.24186600 1.53772500
H 0.00000000 7.44095100 -1.28390200
H -5.28485000 5.26917900 -1.26496700
H -2.29755200 2.29167800 1.53383100
H 2.29755200 2.29167800 1.53383100
H 5.28485000 5.26917900 -1.26496700
H -3.24951400 0.00000000 1.53050900
H -7.48486300 0.00000000 -1.24596900
H 2.89290200 6.95367400 -1.34876500
H -6.99469100 2.88478800 -1.32543800
H -6.99469100 -2.88478800 -1.32543800
H -2.89290200 -6.95367400 -1.34876500
H 6.99469100 -2.88478800 -1.32543800
H 6.99469100 2.88478800 -1.32543800
H -2.89290200 6.95367400 -1.34876500
H 2.89290200 -6.95367400 -1.34876500
8MC (C2v)-septet:
C 1.21017000 -5.95469000 -0.24460300
C 1.18961400 -4.73909300 0.52892000
C 0.00000000 -4.15413900 0.94384900
C -1.18961400 -4.73909300 0.52892000
C -1.21017000 -5.95469000 -0.24460300
C 0.00000000 -6.58357300 -0.59944100
C -2.56663500 -6.16922300 -0.66875700
C 2.56663500 -6.16922300 -0.66875700
C 2.52448500 -4.18778000 0.52288800
C -2.52448500 -4.18778000 0.52288800
C 3.36800200 -5.06937900 -0.25378600
C 4.68129900 -4.66281900 -0.60660800
C 5.09331400 -3.36768700 -0.26211800
C 4.21584200 -2.51504300 0.50955000
C 2.95932600 -2.93782500 0.93411000
C -2.95932600 -2.93782500 0.93411000
C -4.21584200 -2.51504300 0.50955000
C -5.09331400 -3.36768700 -0.26211800
C -4.68129900 -4.66281900 -0.60660800
C -3.36800200 -5.06937900 -0.25378600
C 5.99467300 1.21316000 -0.27130500
C 4.76689100 1.18920500 0.50356800
C 4.18603200 0.00000000 0.92446900
S57
C 4.76689100 -1.18920500 0.50356800
C 5.99467300 -1.21316000 -0.27130500
C 6.63153700 0.00000000 -0.61333700
C 6.21501500 -2.56287500 -0.67743900
C 6.21501500 2.56287500 -0.67743900
C -1.21017000 5.95469000 -0.24460300
C -1.18961400 4.73909300 0.52892000
C 0.00000000 4.15413900 0.94384900
C 1.18961400 4.73909300 0.52892000
C 1.21017000 5.95469000 -0.24460300
C 0.00000000 6.58357300 -0.59944100
C 2.56663500 6.16922300 -0.66875700
C -2.56663500 6.16922300 -0.66875700
C -2.52448500 4.18778000 0.52288800
C 2.52448500 4.18778000 0.52288800
C -3.36800200 5.06937900 -0.25378600
C -4.68129900 4.66281900 -0.60660800
C -5.09331400 3.36768700 -0.26211800
C -4.21584200 2.51504300 0.50955000
C -2.95932600 2.93782500 0.93411000
C 2.95932600 2.93782500 0.93411000
C 4.21584200 2.51504300 0.50955000
C 5.09331400 3.36768700 -0.26211800
C 4.68129900 4.66281900 -0.60660800
C 3.36800200 5.06937900 -0.25378600
C -5.99467300 -1.21316000 -0.27130500
C -4.76689100 -1.18920500 0.50356800
C -4.18603200 0.00000000 0.92446900
C -4.76689100 1.18920500 0.50356800
C -5.99467300 1.21316000 -0.27130500
C -6.63153700 0.00000000 -0.61333700
C -6.21501500 2.56287500 -0.67743900
C -6.21501500 -2.56287500 -0.67743900
H 0.00000000 -3.21209700 1.48578600
H 0.00000000 -7.47906400 -1.21599600
H 5.31127900 -5.30414200 -1.21756500
H 2.29977800 -2.26659400 1.47744900
H -2.29977800 -2.26659400 1.47744900
H -5.31127900 -5.30414200 -1.21756500
H 3.24615700 0.00000000 1.46948400
H 7.53368100 0.00000000 -1.21908200
H 0.00000000 3.21209700 1.48578600
H 0.00000000 7.47906400 -1.21599600
H -5.31127900 5.30414200 -1.21756500
H -2.29977800 2.26659400 1.47744900
H 2.29977800 2.26659400 1.47744900
S58
H 5.31127900 5.30414200 -1.21756500
H -3.24615700 0.00000000 1.46948400
H -7.53368100 0.00000000 -1.21908200
H 2.90475100 6.99434800 -1.28540800
H -7.04078000 2.90875800 -1.28770400
H -7.04078000 -2.90875800 -1.28770400
H -2.90475100 -6.99434800 -1.28540800
H 7.04078000 -2.90875800 -1.28770400
H 7.04078000 2.90875800 -1.28770400
H -2.90475100 6.99434800 -1.28540800
H 2.90475100 -6.99434800 -1.28540800
8MC (C2v)-nonet:
C 1.21146500 -5.99617200 -0.24816400
C 1.18674000 -4.77006800 0.49635300
C 0.00000000 -4.17579800 0.90299200
C -1.18674000 -4.77006800 0.49635300
C -1.21146500 -5.99617200 -0.24816400
C 0.00000000 -6.63713100 -0.58560300
C -2.57748100 -6.22259100 -0.64873500
C 2.57748100 -6.22259100 -0.64873500
C 2.53378500 -4.21208800 0.49634800
C -2.53378500 -4.21208800 0.49634800
C 3.38329700 -5.09656000 -0.24814300
C 4.69316500 -4.69316200 -0.58558200
C 5.09656300 -3.38329600 -0.24813900
C 4.21209000 -2.53378500 0.49635200
C 2.95268300 -2.95268200 0.90292000
C -2.95268300 -2.95268200 0.90292000
C -4.21209000 -2.53378500 0.49635200
C -5.09656300 -3.38329600 -0.24813900
C -4.69316500 -4.69316200 -0.58558200
C -3.38329700 -5.09656000 -0.24814300
C 5.99617600 1.21146500 -0.24815300
C 4.77007000 1.18674000 0.49636000
C 4.17579900 0.00000000 0.90299700
C 4.77007000 -1.18674000 0.49636000
C 5.99617600 -1.21146500 -0.24815300
C 6.63713600 0.00000000 -0.58559000
C 6.22259700 -2.57748100 -0.64872400
C 6.22259700 2.57748100 -0.64872400
C -1.21146500 5.99617200 -0.24816400
C -1.18674000 4.77006800 0.49635300
C 0.00000000 4.17579800 0.90299200
C 1.18674000 4.77006800 0.49635300
S59
C 1.21146500 5.99617200 -0.24816400
C 0.00000000 6.63713100 -0.58560300
C 2.57748100 6.22259100 -0.64873500
C -2.57748100 6.22259100 -0.64873500
C -2.53378500 4.21208800 0.49634800
C 2.53378500 4.21208800 0.49634800
C -3.38329700 5.09656000 -0.24814300
C -4.69316500 4.69316200 -0.58558200
C -5.09656300 3.38329600 -0.24813900
C -4.21209000 2.53378500 0.49635200
C -2.95268300 2.95268200 0.90292000
C 2.95268300 2.95268200 0.90292000
C 4.21209000 2.53378500 0.49635200
C 5.09656300 3.38329600 -0.24813900
C 4.69316500 4.69316200 -0.58558200
C 3.38329700 5.09656000 -0.24814300
C -5.99617600 -1.21146500 -0.24815300
C -4.77007000 -1.18674000 0.49636000
C -4.17579900 0.00000000 0.90299700
C -4.77007000 1.18674000 0.49636000
C -5.99617600 1.21146500 -0.24815300
C -6.63713600 0.00000000 -0.58559000
C -6.22259700 2.57748100 -0.64872400
C -6.22259700 -2.57748100 -0.64872400
H 0.00000000 -3.22489200 1.42852200
H 0.00000000 -7.54855400 -1.17736700
H 5.33764900 -5.33764600 -1.17732100
H 2.28020600 -2.28020700 1.42824300
H -2.28020600 -2.28020700 1.42824300
H -5.33764900 -5.33764600 -1.17732100
H 3.22489100 0.00000000 1.42852400
H 7.54856200 0.00000000 -1.17735100
H 0.00000000 3.22489200 1.42852200
H 0.00000000 7.54855400 -1.17736700
H -5.33764900 5.33764600 -1.17732100
H -2.28020600 2.28020700 1.42824300
H 2.28020600 2.28020700 1.42824300
H 5.33764900 5.33764600 -1.17732100
H -3.22489100 0.00000000 1.42852400
H -7.54856200 0.00000000 -1.17735100
H 2.92475700 7.06098100 -1.24132800
H -7.06098900 2.92475700 -1.24131400
H -7.06098900 -2.92475700 -1.24131400
H -2.92475700 -7.06098100 -1.24132800
H 7.06098900 -2.92475700 -1.24131400
H 7.06098900 2.92475700 -1.24131400
S60
H -2.92475700 7.06098100 -1.24132800
H 2.92475700 -7.06098100 -1.24132800
10MC (D2h)-singlet:
H 0.00000000 -8.80855700 2.85942500
H 0.00000000 -8.80855700 -2.85942500
H 0.00000000 -5.44234000 -7.48372300
H 0.00000000 0.00000000 -9.24885500
H 0.00000000 5.44234000 -7.48372300
H 0.00000000 8.80855700 -2.85942500
C 0.00000000 8.28328400 0.00000000
C 0.00000000 6.70137100 4.86128800
C 0.00000000 2.55988200 7.86651300
C 0.00000000 -2.55988200 7.86651300
C 0.00000000 -6.70137100 4.86128800
C 0.00000000 -8.28328400 0.00000000
C 0.00000000 -6.70137100 -4.86128800
C 0.00000000 -2.55988200 -7.86651300
C 0.00000000 2.55988200 -7.86651300
C 0.00000000 6.70137100 -4.86128800
H 0.00000000 9.36718800 0.00000000
H 0.00000000 7.57757100 5.49936600
H 0.00000000 2.89417800 8.89758800
H 0.00000000 -2.89417800 8.89758800
H 0.00000000 -7.57757100 5.49936600
H 0.00000000 -9.36718800 0.00000000
H 0.00000000 -7.57757100 -5.49936600
H 0.00000000 -2.89417800 -8.89758800
H 0.00000000 2.89417800 -8.89758800
H 0.00000000 7.57757100 -5.49936600
C 0.00000000 5.32927800 2.98566900
C 0.00000000 2.55476100 5.54305900
C 0.00000000 -1.19440500 5.98432300
C 0.00000000 -4.48887400 4.14043900
C 0.00000000 -6.06917600 0.71334200
C 0.00000000 -5.32927800 -2.98566900
C 0.00000000 -2.55476100 -5.54305900
C 0.00000000 1.19440500 -5.98432300
C 0.00000000 4.48887400 -4.14043900
C 0.00000000 6.06917600 -0.71334200
C 0.00000000 6.06917600 0.71334200
C 0.00000000 4.48887400 4.14043900
C 0.00000000 1.19440500 5.98432300
C 0.00000000 -2.55476100 5.54305900
C 0.00000000 -5.32927800 2.98566900
S61
C 0.00000000 -6.06917600 -0.71334200
C 0.00000000 -4.48887400 -4.14043900
C 0.00000000 -1.19440500 -5.98432300
C 0.00000000 2.55476100 -5.54305900
C 0.00000000 5.32927800 -2.98566900
C 0.00000000 6.71857100 3.44813000
C 0.00000000 3.40505000 6.73076500
C 0.00000000 -1.20463000 7.44312700
C 0.00000000 -5.35606500 5.31627300
C 0.00000000 -7.46517200 1.15589100
C 0.00000000 -6.71857100 -3.44813000
C 0.00000000 -3.40505000 -6.73076500
C 0.00000000 1.20463000 -7.44312700
C 0.00000000 5.35606500 -5.31627300
C 0.00000000 7.46517200 -1.15589100
C 0.00000000 7.46517200 1.15589100
C 0.00000000 5.35606500 5.31627300
C 0.00000000 1.20463000 7.44312700
C 0.00000000 -3.40505000 6.73076500
C 0.00000000 -6.71857100 3.44813000
C 0.00000000 -7.46517200 -1.15589100
C 0.00000000 -5.35606500 -5.31627300
C 0.00000000 -1.20463000 -7.44312700
C 0.00000000 3.40505000 -6.73076500
C 0.00000000 6.71857100 -3.44813000
10MC (D2h)-triplet:
H 0.00000000 3.98078800 1.29344600
H 0.00000000 2.46037500 3.38604000
H 0.00000000 0.00000000 4.18537300
H 0.00000000 -2.46037500 3.38604000
H 0.00000000 -3.98078800 1.29344600
H 0.00000000 -3.98078800 -1.29344600
H 0.00000000 -2.46037500 -3.38604000
H 0.00000000 0.00000000 -4.18537300
H 0.00000000 2.46037500 -3.38604000
H 0.00000000 3.98078800 -1.29344600
C 0.00000000 5.01462400 1.62932200
C 0.00000000 3.09924900 4.26550300
C 0.00000000 0.00000000 5.27240100
C 0.00000000 -3.09924900 4.26550300
C 0.00000000 -5.01462400 1.62932200
C 0.00000000 -5.01462400 -1.62932200
C 0.00000000 -3.09924900 -4.26550300
C 0.00000000 0.00000000 -5.27240100
S62
C 0.00000000 3.09924900 -4.26550300
C 0.00000000 5.01462400 -1.62932200
C 0.00000000 7.76814500 2.52400000
C 0.00000000 4.80091300 6.60787200
C 0.00000000 0.00000000 8.16764700
C 0.00000000 -4.80091300 6.60787200
C 0.00000000 -7.76814500 2.52400000
C 0.00000000 -7.76814500 -2.52400000
C 0.00000000 -4.80091300 -6.60787200
C 0.00000000 0.00000000 -8.16764700
C 0.00000000 4.80091300 -6.60787200
C 0.00000000 7.76814500 -2.52400000
H 0.00000000 8.80180800 2.85983400
H 0.00000000 5.43969500 7.48718600
H 0.00000000 0.00000000 9.25449500
H 0.00000000 -5.43969500 7.48718600
H 0.00000000 -8.80180800 2.85983400
H 0.00000000 -8.80180800 -2.85983400
H 0.00000000 -5.43969500 -7.48718600
H 0.00000000 0.00000000 -9.25449500
H 0.00000000 5.43969500 -7.48718600
H 0.00000000 8.80180800 -2.85983400
C 0.00000000 8.27614600 0.00000000
C 0.00000000 6.69555500 4.86457800
C 0.00000000 2.55741200 7.87087600
C 0.00000000 -2.55741200 7.87087600
C 0.00000000 -6.69555500 4.86457800
C 0.00000000 -8.27614600 0.00000000
C 0.00000000 -6.69555500 -4.86457800
C 0.00000000 -2.55741200 -7.87087600
C 0.00000000 2.55741200 -7.87087600
C 0.00000000 6.69555500 -4.86457800
H 0.00000000 9.36006700 0.00000000
H 0.00000000 7.57244700 5.50171300
H 0.00000000 2.89232800 8.90175500
H 0.00000000 -2.89232800 8.90175500
H 0.00000000 -7.57244700 5.50171300
H 0.00000000 -9.36006700 0.00000000
H 0.00000000 -7.57244700 -5.50171300
H 0.00000000 -2.89232800 -8.90175500
H 0.00000000 2.89232800 -8.90175500
H 0.00000000 7.57244700 -5.50171300
C 0.00000000 5.32498300 2.98622400
C 0.00000000 2.55266000 5.54564300
C 0.00000000 -1.19460500 5.98685400
C 0.00000000 -4.48563900 4.14141700
S63
C 0.00000000 -6.06323900 0.71396500
C 0.00000000 -5.32498300 -2.98622400
C 0.00000000 -2.55266000 -5.54564300
C 0.00000000 1.19460500 -5.98685400
C 0.00000000 4.48563900 -4.14141700
C 0.00000000 6.06323900 -0.71396500
C 0.00000000 6.06323900 0.71396500
C 0.00000000 4.48563900 4.14141700
C 0.00000000 1.19460500 5.98685400
C 0.00000000 -2.55266000 5.54564300
C 0.00000000 -5.32498300 2.98622400
C 0.00000000 -6.06323900 -0.71396500
C 0.00000000 -4.48563900 -4.14141700
C 0.00000000 -1.19460500 -5.98685400
C 0.00000000 2.55266000 -5.54564300
C 0.00000000 5.32498300 -2.98622400
C 0.00000000 6.71240100 3.44802900
C 0.00000000 3.40366300 6.73478100
C 0.00000000 -1.20503100 7.44909800
C 0.00000000 -5.35352900 5.31827600
C 0.00000000 -7.45712000 1.15589300
C 0.00000000 -6.71240100 -3.44802900
C 0.00000000 -3.40366300 -6.73478100
C 0.00000000 1.20503100 -7.44909800
C 0.00000000 5.35352900 -5.31827600
C 0.00000000 7.45712000 -1.15589300
C 0.00000000 7.45712000 1.15589300
C 0.00000000 5.35352900 5.31827600
C 0.00000000 1.20503100 7.44909800
C 0.00000000 -3.40366300 6.73478100
C 0.00000000 -6.71240100 3.44802900
C 0.00000000 -7.45712000 -1.15589300
C 0.00000000 -5.35352900 -5.31827600
C 0.00000000 -1.20503100 -7.44909800
C 0.00000000 3.40366300 -6.73478100
C 0.00000000 6.71240100 -3.44802900
10MC (D2h)-quintet:
H 0.00000000 3.94876200 1.31003100
H 0.00000000 2.43801500 3.42659900
H 0.00000000 0.00000000 4.23296700
H 0.00000000 -2.43801500 3.42659900
H 0.00000000 -3.94876200 1.31003100
H 0.00000000 -3.94876200 -1.31003100
H 0.00000000 -2.43801500 -3.42659900
S64
H 0.00000000 0.00000000 -4.23296700
H 0.00000000 2.43801500 -3.42659900
H 0.00000000 3.94876200 -1.31003100
C 0.00000000 4.98483600 1.63946700
C 0.00000000 3.08592500 4.29945800
C 0.00000000 0.00000000 5.31994100
C 0.00000000 -3.08592500 4.29945800
C 0.00000000 -4.98483600 1.63946700
C 0.00000000 -4.98483600 -1.63946700
C 0.00000000 -3.08592500 -4.29945800
C 0.00000000 0.00000000 -5.31994100
C 0.00000000 3.08592500 -4.29945800
C 0.00000000 4.98483600 -1.63946700
C 0.00000000 7.73185600 2.52803100
C 0.00000000 4.79217800 6.63787600
C 0.00000000 0.00000000 8.21915600
C 0.00000000 -4.79217800 6.63787600
C 0.00000000 -7.73185600 2.52803100
C 0.00000000 -7.73185600 -2.52803100
C 0.00000000 -4.79217800 -6.63787600
C 0.00000000 0.00000000 -8.21915600
C 0.00000000 4.79217800 -6.63787600
C 0.00000000 7.73185600 -2.52803100
H 0.00000000 8.76787500 2.85801000
H 0.00000000 5.43934900 7.51108400
H 0.00000000 0.00000000 9.30577000
H 0.00000000 -5.43934900 7.51108400
H 0.00000000 -8.76787500 2.85801000
H 0.00000000 -8.76787500 -2.85801000
H 0.00000000 -5.43934900 -7.51108400
H 0.00000000 0.00000000 -9.30577000
H 0.00000000 5.43934900 -7.51108400
H 0.00000000 8.76787500 -2.85801000
C 0.00000000 8.23477700 0.00000000
C 0.00000000 6.67380500 4.88146400
C 0.00000000 2.55622800 7.92041400
C 0.00000000 -2.55622800 7.92041400
C 0.00000000 -6.67380500 4.88146400
C 0.00000000 -8.23477700 0.00000000
C 0.00000000 -6.67380500 -4.88146400
C 0.00000000 -2.55622800 -7.92041400
C 0.00000000 2.55622800 -7.92041400
C 0.00000000 6.67380500 -4.88146400
H 0.00000000 9.31916200 0.00000000
H 0.00000000 7.55504600 5.51281200
H 0.00000000 2.89535200 8.94949700
S65
H 0.00000000 -2.89535200 8.94949700
H 0.00000000 -7.55504600 5.51281200
H 0.00000000 -9.31916200 0.00000000
H 0.00000000 -7.55504600 -5.51281200
H 0.00000000 -2.89535200 -8.94949700
H 0.00000000 2.89535200 -8.94949700
H 0.00000000 7.55504600 -5.51281200
C 0.00000000 5.30255700 2.99648000
C 0.00000000 2.54959900 5.58584100
C 0.00000000 -1.19485800 6.03333500
C 0.00000000 -4.46921300 4.16204100
C 0.00000000 -6.02743100 0.71861100
C 0.00000000 -5.30255700 -2.99648000
C 0.00000000 -2.54959900 -5.58584100
C 0.00000000 1.19485800 -6.03333500
C 0.00000000 4.46921300 -4.16204100
C 0.00000000 6.02743100 -0.71861100
C 0.00000000 6.02743100 0.71861100
C 0.00000000 4.46921300 4.16204100
C 0.00000000 1.19485800 6.03333500
C 0.00000000 -2.54959900 5.58584100
C 0.00000000 -5.30255700 2.99648000
C 0.00000000 -6.02743100 -0.71861100
C 0.00000000 -4.46921300 -4.16204100
C 0.00000000 -1.19485800 -6.03333500
C 0.00000000 2.54959900 -5.58584100
C 0.00000000 5.30255700 -2.99648000
C 0.00000000 6.68339700 3.44930900
C 0.00000000 3.40559800 6.77055500
C 0.00000000 -1.20804400 7.49950800
C 0.00000000 -5.34333100 5.33272900
C 0.00000000 -7.41335700 1.15467000
C 0.00000000 -6.68339700 -3.44930900
C 0.00000000 -3.40559800 -6.77055500
C 0.00000000 1.20804400 -7.49950800
C 0.00000000 5.34333100 -5.33272900
C 0.00000000 7.41335700 -1.15467000
C 0.00000000 7.41335700 1.15467000
C 0.00000000 5.34333100 5.33272900
C 0.00000000 1.20804400 7.49950800
C 0.00000000 -3.40559800 6.77055500
C 0.00000000 -6.68339700 3.44930900
C 0.00000000 -7.41335700 -1.15467000
C 0.00000000 -5.34333100 -5.33272900
C 0.00000000 -1.20804400 -7.49950800
C 0.00000000 3.40559800 -6.77055500
S66
C 0.00000000 6.68339700 -3.44930900
10MC (D2h)-septet:
H 0.00000000 4.00689300 1.30067100
H 0.00000000 2.47485700 3.40246000
H 0.00000000 0.00000000 4.20440800
H 0.00000000 -2.47485700 3.40246000
H 0.00000000 -4.00689300 1.30067100
H 0.00000000 -4.00689300 -1.30067100
H 0.00000000 -2.47485700 -3.40246000
H 0.00000000 0.00000000 -4.20440800
H 0.00000000 2.47485700 -3.40246000
H 0.00000000 4.00689300 -1.30067100
C 0.00000000 5.04100700 1.63684800
C 0.00000000 3.11369700 4.28191600
C 0.00000000 0.00000000 5.29121500
C 0.00000000 -3.11369700 4.28191600
C 0.00000000 -5.04100700 1.63684800
C 0.00000000 -5.04100700 -1.63684800
C 0.00000000 -3.11369700 -4.28191600
C 0.00000000 0.00000000 -5.29121500
C 0.00000000 3.11369700 -4.28191600
C 0.00000000 5.04100700 -1.63684800
C 0.00000000 7.79085400 2.52536700
C 0.00000000 4.81587700 6.61299100
C 0.00000000 0.00000000 8.17555000
C 0.00000000 -4.81587700 6.61299100
C 0.00000000 -7.79085400 2.52536700
C 0.00000000 -7.79085400 -2.52536700
C 0.00000000 -4.81587700 -6.61299100
C 0.00000000 0.00000000 -8.17555000
C 0.00000000 4.81587700 -6.61299100
C 0.00000000 7.79085400 -2.52536700
H 0.00000000 8.82438500 2.86207200
H 0.00000000 5.45403500 7.49262400
H 0.00000000 0.00000000 9.26214600
H 0.00000000 -5.45403500 7.49262400
H 0.00000000 -8.82438500 2.86207200
H 0.00000000 -8.82438500 -2.86207200
H 0.00000000 -5.45403500 -7.49262400
H 0.00000000 0.00000000 -9.26214600
H 0.00000000 5.45403500 -7.49262400
H 0.00000000 8.82438500 -2.86207200
C 0.00000000 8.30494100 0.00000000
C 0.00000000 6.72007000 4.86635200
S67
C 0.00000000 2.56818800 7.87871200
C 0.00000000 -2.56818800 7.87871200
C 0.00000000 -6.72007000 4.86635200
C 0.00000000 -8.30494100 0.00000000
C 0.00000000 -6.72007000 -4.86635200
C 0.00000000 -2.56818800 -7.87871200
C 0.00000000 2.56818800 -7.87871200
C 0.00000000 6.72007000 -4.86635200
H 0.00000000 9.38866400 0.00000000
H 0.00000000 7.59597000 5.50473000
H 0.00000000 2.90228800 8.90991900
H 0.00000000 -2.90228800 8.90991900
H 0.00000000 -7.59597000 5.50473000
H 0.00000000 -9.38866400 0.00000000
H 0.00000000 -7.59597000 -5.50473000
H 0.00000000 -2.90228800 -8.90991900
H 0.00000000 2.90228800 -8.90991900
H 0.00000000 7.59597000 -5.50473000
C 0.00000000 5.35177100 2.98942600
C 0.00000000 2.57501400 5.55822100
C 0.00000000 -1.19332000 6.00908100
C 0.00000000 -4.50865200 4.15517800
C 0.00000000 -6.09286900 0.71383700
C 0.00000000 -5.35177100 -2.98942600
C 0.00000000 -2.57501400 -5.55822100
C 0.00000000 1.19332000 -6.00908100
C 0.00000000 4.50865200 -4.15517800
C 0.00000000 6.09286900 -0.71383700
C 0.00000000 6.09286900 0.71383700
C 0.00000000 4.50865200 4.15517800
C 0.00000000 1.19332000 6.00908100
C 0.00000000 -2.57501400 5.55822100
C 0.00000000 -5.35177100 2.98942600
C 0.00000000 -6.09286900 -0.71383700
C 0.00000000 -4.50865200 -4.15517800
C 0.00000000 -1.19332000 -6.00908100
C 0.00000000 2.57501400 -5.55822100
C 0.00000000 5.35177100 -2.98942600
C 0.00000000 6.73401500 3.44989400
C 0.00000000 3.41808000 6.73752300
C 0.00000000 -1.20431500 7.45399200
C 0.00000000 -5.36860800 5.32121000
C 0.00000000 -7.48099700 1.15462700
C 0.00000000 -6.73401500 -3.44989400
C 0.00000000 -3.41808000 -6.73752300
C 0.00000000 1.20431500 -7.45399200
S68
C 0.00000000 5.36860800 -5.32121000
C 0.00000000 7.48099700 -1.15462700
C 0.00000000 7.48099700 1.15462700
C 0.00000000 5.36860800 5.32121000
C 0.00000000 1.20431500 7.45399200
C 0.00000000 -3.41808000 6.73752300
C 0.00000000 -6.73401500 3.44989400
C 0.00000000 -7.48099700 -1.15462700
C 0.00000000 -5.36860800 -5.32121000
C 0.00000000 -1.20431500 -7.45399200
C 0.00000000 3.41808000 -6.73752300
C 0.00000000 6.73401500 -3.44989400
10MC (D2h)-nonet:
H 0.00000000 4.02083500 1.29368800
H 0.00000000 2.47357600 3.41646900
H 0.00000000 0.00000000 4.22664200
H 0.00000000 -2.47357600 3.41646900
H 0.00000000 -4.02083500 1.29368800
H 0.00000000 -4.02083500 -1.29368800
H 0.00000000 -2.47357600 -3.41646900
H 0.00000000 0.00000000 -4.22664200
H 0.00000000 2.47357600 -3.41646900
H 0.00000000 4.02083500 -1.29368800
C 0.00000000 5.05248900 1.63608000
C 0.00000000 3.11591000 4.29357000
C 0.00000000 0.00000000 5.31354400
C 0.00000000 -3.11591000 4.29357000
C 0.00000000 -5.05248900 1.63608000
C 0.00000000 -5.05248900 -1.63608000
C 0.00000000 -3.11591000 -4.29357000
C 0.00000000 0.00000000 -5.31354400
C 0.00000000 3.11591000 -4.29357000
C 0.00000000 5.05248900 -1.63608000
C 0.00000000 7.79480400 2.53058700
C 0.00000000 4.81057600 6.62287900
C 0.00000000 0.00000000 8.20035500
C 0.00000000 -4.81057600 6.62287900
C 0.00000000 -7.79480400 2.53058700
C 0.00000000 -7.79480400 -2.53058700
C 0.00000000 -4.81057600 -6.62287900
C 0.00000000 0.00000000 -8.20035500
C 0.00000000 4.81057600 -6.62287900
C 0.00000000 7.79480400 -2.53058700
H 0.00000000 8.82586200 2.87365600
S69
H 0.00000000 5.45310300 7.49939000
H 0.00000000 0.00000000 9.28689000
H 0.00000000 -5.45310300 7.49939000
H 0.00000000 -8.82586200 2.87365600
H 0.00000000 -8.82586200 -2.87365600
H 0.00000000 -5.45310300 -7.49939000
H 0.00000000 0.00000000 -9.28689000
H 0.00000000 5.45310300 -7.49939000
H 0.00000000 8.82586200 -2.87365600
C 0.00000000 8.32162200 0.00000000
C 0.00000000 6.71033600 4.87300000
C 0.00000000 2.56544200 7.90425700
C 0.00000000 -2.56544200 7.90425700
C 0.00000000 -6.71033600 4.87300000
C 0.00000000 -8.32162200 0.00000000
C 0.00000000 -6.71033600 -4.87300000
C 0.00000000 -2.56544200 -7.90425700
C 0.00000000 2.56544200 -7.90425700
C 0.00000000 6.71033600 -4.87300000
H 0.00000000 9.40494900 0.00000000
H 0.00000000 7.58617000 5.51182900
H 0.00000000 2.90330500 8.93384100
H 0.00000000 -2.90330500 8.93384100
H 0.00000000 -7.58617000 5.51182900
H 0.00000000 -9.40494900 0.00000000
H 0.00000000 -7.58617000 -5.51182900
H 0.00000000 -2.90330500 -8.93384100
H 0.00000000 2.90330500 -8.93384100
H 0.00000000 7.58617000 -5.51182900
C 0.00000000 5.35859700 2.98969600
C 0.00000000 2.57271000 5.58060300
C 0.00000000 -1.19473800 6.03083800
C 0.00000000 -4.50022200 4.16842300
C 0.00000000 -6.11203800 0.72209500
C 0.00000000 -5.35859700 -2.98969600
C 0.00000000 -2.57271000 -5.58060300
C 0.00000000 1.19473800 -6.03083800
C 0.00000000 4.50022200 -4.16842300
C 0.00000000 6.11203800 -0.72209500
C 0.00000000 6.11203800 0.72209500
C 0.00000000 4.50022200 4.16842300
C 0.00000000 1.19473800 6.03083800
C 0.00000000 -2.57271000 5.58060300
C 0.00000000 -5.35859700 2.98969600
C 0.00000000 -6.11203800 -0.72209500
C 0.00000000 -4.50022200 -4.16842300
S70
C 0.00000000 -1.19473800 -6.03083800
C 0.00000000 2.57271000 -5.58060300
C 0.00000000 5.35859700 -2.98969600
C 0.00000000 6.72935300 3.45092300
C 0.00000000 3.41450900 6.75215000
C 0.00000000 -1.20614900 7.47956700
C 0.00000000 -5.35817400 5.32793000
C 0.00000000 -7.48990700 1.16272500
C 0.00000000 -6.72935300 -3.45092300
C 0.00000000 -3.41450900 -6.75215000
C 0.00000000 1.20614900 -7.47956700
C 0.00000000 5.35817400 -5.32793000
C 0.00000000 7.48990700 -1.16272500
C 0.00000000 7.48990700 1.16272500
C 0.00000000 5.35817400 5.32793000
C 0.00000000 1.20614900 7.47956700
C 0.00000000 -3.41450900 6.75215000
C 0.00000000 -6.72935300 3.45092300
C 0.00000000 -7.48990700 -1.16272500
C 0.00000000 -5.35817400 -5.32793000
C 0.00000000 -1.20614900 -7.47956700
C 0.00000000 3.41450900 -6.75215000
C 0.00000000 6.72935300 -3.45092300
10MC (D2h)-11-et:
H 0.00000000 4.00980900 1.30287200
H 0.00000000 2.47831500 3.41072300
H 0.00000000 0.00000000 4.21589900
H 0.00000000 -2.47831500 3.41072300
H 0.00000000 -4.00980900 1.30287200
H 0.00000000 -4.00980900 -1.30287200
H 0.00000000 -2.47831500 -3.41072300
H 0.00000000 0.00000000 -4.21589900
H 0.00000000 2.47831500 -3.41072300
H 0.00000000 4.00980900 -1.30287200
C 0.00000000 5.04353000 1.63871400
C 0.00000000 3.11711100 4.29009600
C 0.00000000 0.00000000 5.30280700
C 0.00000000 -3.11711100 4.29009600
C 0.00000000 -5.04353000 1.63871400
C 0.00000000 -5.04353000 -1.63871400
C 0.00000000 -3.11711100 -4.29009600
C 0.00000000 0.00000000 -5.30280700
C 0.00000000 3.11711100 -4.29009600
C 0.00000000 5.04353000 -1.63871400
S71
C 0.00000000 7.78956200 2.53095400
C 0.00000000 4.81415000 6.62607700
C 0.00000000 0.00000000 8.19015900
C 0.00000000 -4.81415000 6.62607700
C 0.00000000 -7.78956200 2.53095400
C 0.00000000 -7.78956200 -2.53095400
C 0.00000000 -4.81415000 -6.62607700
C 0.00000000 0.00000000 -8.19015900
C 0.00000000 4.81415000 -6.62607700
C 0.00000000 7.78956200 -2.53095400
H 0.00000000 8.82279600 2.86665100
H 0.00000000 5.45266300 7.50503200
H 0.00000000 0.00000000 9.27655800
H 0.00000000 -5.45266300 7.50503200
H 0.00000000 -8.82279600 2.86665100
H 0.00000000 -8.82279600 -2.86665100
H 0.00000000 -5.45266300 -7.50503200
H 0.00000000 0.00000000 -9.27655800
H 0.00000000 5.45266300 -7.50503200
H 0.00000000 8.82279600 -2.86665100
C 0.00000000 8.30619200 0.00000000
C 0.00000000 6.71986500 4.88222200
C 0.00000000 2.56670400 7.89944700
C 0.00000000 -2.56670400 7.89944700
C 0.00000000 -6.71986500 4.88222200
C 0.00000000 -8.30619200 0.00000000
C 0.00000000 -6.71986500 -4.88222200
C 0.00000000 -2.56670400 -7.89944700
C 0.00000000 2.56670400 -7.89944700
C 0.00000000 6.71986500 -4.88222200
H 0.00000000 9.38939300 0.00000000
H 0.00000000 7.59618000 5.51892700
H 0.00000000 2.90140800 8.92963900
H 0.00000000 -2.90140800 8.92963900
H 0.00000000 -7.59618000 5.51892700
H 0.00000000 -9.38939300 0.00000000
H 0.00000000 -7.59618000 -5.51892700
H 0.00000000 -2.90140800 -8.92963900
H 0.00000000 2.90140800 -8.92963900
H 0.00000000 7.59618000 -5.51892700
C 0.00000000 5.35595700 2.99588100
C 0.00000000 2.57204700 5.57166800
C 0.00000000 -1.19421900 6.01931400
C 0.00000000 -4.50440500 4.16789600
C 0.00000000 -6.09398600 0.72435300
C 0.00000000 -5.35595700 -2.99588100
S72
C 0.00000000 -2.57204700 -5.57166800
C 0.00000000 1.19421900 -6.01931400
C 0.00000000 4.50440500 -4.16789600
C 0.00000000 6.09398600 -0.72435300
C 0.00000000 6.09398600 0.72435300
C 0.00000000 4.50440500 4.16789600
C 0.00000000 1.19421900 6.01931400
C 0.00000000 -2.57204700 5.57166800
C 0.00000000 -5.35595700 2.99588100
C 0.00000000 -6.09398600 -0.72435300
C 0.00000000 -4.50440500 -4.16789600
C 0.00000000 -1.19421900 -6.01931400
C 0.00000000 2.57204700 -5.57166800
C 0.00000000 5.35595700 -2.99588100
C 0.00000000 6.73131400 3.45455700
C 0.00000000 3.41512600 6.75117700
C 0.00000000 -1.20540400 7.46910400
C 0.00000000 -5.36559200 5.33423400
C 0.00000000 -7.47626800 1.16171900
C 0.00000000 -6.73131400 -3.45455700
C 0.00000000 -3.41512600 -6.75117700
C 0.00000000 1.20540400 -7.46910400
C 0.00000000 5.36559200 -5.33423400
C 0.00000000 7.47626800 -1.16171900
C 0.00000000 7.47626800 1.16171900
C 0.00000000 5.36559200 5.33423400
C 0.00000000 1.20540400 7.46910400
C 0.00000000 -3.41512600 6.75117700
C 0.00000000 -6.73131400 3.45455700
C 0.00000000 -7.47626800 -1.16171900
C 0.00000000 -5.36559200 -5.33423400
C 0.00000000 -1.20540400 -7.46910400
C 0.00000000 3.41512600 -6.75117700
C 0.00000000 6.73131400 -3.45455700
8MC-M (singlet, for NMR calculation):
C -5.11809265 3.27771517 -1.21291696
C -4.23546840 2.44523259 -2.03376163
C -2.99578793 2.90227583 -2.46079285
C -2.57643653 4.15460312 -2.03108948
C -3.43653495 5.01013454 -1.20992576
C -4.72163030 4.57468450 -0.83987783
C -1.30075811 5.93449096 -1.20881086
C -1.26556517 4.72239452 -2.03104624
C -0.06565606 4.17104756 -2.46090492
S73
C 1.11612894 4.76155516 -2.03370100
C 1.11373046 5.97392657 -1.21138503
C -0.10327520 6.57028399 -0.83427949
C 3.27758932 5.11782321 -1.21349074
C 2.44480317 4.23527586 -2.03413686
C 2.90173819 2.99567354 -2.46148845
C 4.15417067 2.57627817 -2.03211394
C 5.01018374 3.43655083 -1.21160027
C 4.57484157 4.72151394 -0.84122734
C 5.93440709 1.30078897 -1.21034552
C 4.72199872 1.26544384 -2.03214873
C 4.17071793 0.06545383 -2.46185703
C 4.76145304 -1.11623016 -2.03467564
C 5.97402193 -1.11364068 -1.21262410
C 6.57058763 0.10341663 -0.83611861
C 5.11826111 -3.27763135 -1.21451188
C 4.23549236 -2.44501891 -2.03512045
C 2.99574510 -2.90203569 -2.46196172
C 2.57646434 -4.15436694 -2.03218144
C 3.43684035 -5.01013379 -1.21151391
C 4.72186392 -4.57464476 -0.84146440
C 1.30096367 -5.93420875 -1.20952816
C 1.26557098 -4.72205345 -2.03171070
C 0.06555445 -4.17064604 -2.46117036
C -1.11610751 -4.76116707 -2.03363045
C -1.11350196 -5.97369305 -1.21148821
C 0.10359397 -6.57020911 -0.83496200
C -3.27745719 -5.11777886 -1.21329523
C -2.44477162 -4.23498219 -2.03381230
C -2.90184637 -2.99535414 -2.46095198
C -4.15418284 -2.57605005 -2.03125761
C -5.00992046 -3.43632716 -1.21043896
C -4.57453368 -4.72146311 -0.84055103
C -5.93457865 -1.30069880 -1.20962952
C -4.72209127 -1.26526626 -2.03127609
C -4.17068407 -0.06523148 -2.46070791
C -4.76132455 1.11639855 -2.03328218
C -5.97404405 1.11376936 -1.21145553
C -6.57066653 -0.10337896 -0.83518375
C -2.64802810 6.11640633 -0.75652412
C 2.45470964 6.19892930 -0.76013319
C 6.11682465 2.64815701 -0.75887457
C 6.19932655 -2.45454909 -0.76140195
C 2.64833234 -6.11636442 -0.75793335
C -2.45437299 -6.19884130 -0.76010276
C -6.11663811 -2.64811473 -0.75777847
S74
C -6.19945340 2.45457775 -0.76017218
H -2.33054049 2.25763478 -3.02560455
H -5.34833297 5.18248601 -0.19691271
H -0.05116911 3.24508005 -3.02610242
H -0.11680119 7.43880922 -0.18552142
H 2.25690459 2.33043691 -3.02609403
H 5.18252342 5.34800450 -0.19795902
H 3.24466536 0.05082257 -3.02691050
H 7.43979460 0.11715584 -0.18827995
H 2.33032431 -2.25731241 -3.02647260
H 5.34837064 -5.18195192 -0.19785800
H 0.05090917 -3.24472979 -3.02644305
H 0.11737147 -7.43924277 -0.18689404
H -2.25718219 -2.33006132 -3.02568065
H -5.18206576 -5.34814855 -0.19733617
H -3.24453885 -0.05055436 -3.02560508
H -7.43938994 -0.11713398 -0.18670151
C -3.11638467 7.19783058 0.14288488
C -3.59132430 8.40908639 -0.40190796
C -3.09181468 7.01174360 1.54152467
C -4.03500022 9.41633168 0.46049773
C -3.54281449 8.04241726 2.37265737
C -4.01548200 9.25024649 1.84924954
H -4.40447280 10.34616242 0.03931782
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8MC bowl shape: KMLYP/6-31G(d,p)
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S78
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S79
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S80
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S81
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S82
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S83
8MC s-shaped transition state: UB3LYP/6-31G(d,p)
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S84
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