Preparation and characterization of 3,5-dinitro-1H-1,2,4 ...Preparation and characterization of...

Preparation and characterization of 3,5-dinitro-1H-1,2,4-triazole

Supplementary Information

R. Haiges, G. Bélanger-Chabot, S. M. Kaplan and K. O. Christe

Loker Hydrocarbon Research Institute, University of Southern California, Los Angeles, CA 90089-1661, USA. E-mail: [email protected]; Tel: +1-213-7403197

Table of Contents

Experimental Details ...............................................................................................................2Materials and apparatus...................................................................................................................2X-ray Crystal Structure Determination ..............................................................................................2Synthesis of potassium 3,5-dinitro-1,2,4-triazolate (method 1).........................................................3Synthesis of potassium 3,5-dinitro-1,2,4-triazolate (method 2).........................................................4Synthesis of 3,5-dinitro-1H-1,2,4-triazole (HDNT) .............................................................................4Synthesis of PPN+ 3,5-dinitro-1,2,4-triazolate [PPN][DNT] .................................................................5

Crystallographic Information ...................................................................................................6Crystal Structure Report for the monoclinic modification HDNT-1 ....................................................6Crystal Structure Report for the triclinic modification HDNT-2 ........................................................13Crystal Structure Report for (HDNT)3·4 H2O.....................................................................................25Crystal Structure Report for 5-ethoxy-1-methyl-3-nitro-1H-1,2,4-triazole 1.....................................37Crystal Structure Report for 1-acetyl-3,5-diamino-1H-1,2,4-triazole 2 .............................................43Crystal Structure Report for 1-(i-propyl)-3,5-dinitro-1H-1,2,4-triazole 3 ..........................................51Crystal Structure Report for the co-crystal of 1-(i-propyl)-3,5-dinitro-1H-1,2,4-triazole and 3-nitro-1H-1,2,4-triazole 3·4. ......................................................................................................................59Crystal Structure Report for sodium 3-nitro-1,2,4-triazol-5-olate monohydrate 5·H2O ....................70Crystal Structure Report for the co-crystal of 5-azido-3-nitro-1,2,4-triazole and PPN+ 5-azido-3-nitro-1,2,4-triazolate 6 ............................................................................................................................77Crystal Structure Report for 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate ........................................................................................................................................91

References ..........................................................................................................................104

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Electronic Supplementary Material (ESI) for Dalton Transactions.This journal is © The Royal Society of Chemistry 2015

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Experimental Details

Caution! The compounds of this work are energetic materials that might explode under certain conditions (e.g., elevated temperature, impact, friction or electric discharge). Appropriate safety precautions, such as the use of shields or barricades in a fume hood and personal protection equipment (safety glasses, face shields, ear plugs, as well as gloves and suits made from leather and/or Kevlar)1 should be taken at all the time when handling these materials. Pure HDNT decomposes explosively when heated above 160 °C, and certain impurities might further lower the decomposition temperature. The sublimation of HDNT should be carried-out behind a blast shield and only on a small scale. Ignoring safety precautions may lead to serious injuries!

Materials and apparatus

All chemicals and solvents were obtained from Sigma-Aldrich or Alfa-Aesar and were used as supplied. NMR spectra were recorded at 298 K on Bruker AMX500 or Varian VNMRS-600s spectrometers using (CD3)2CO or D2O solutions in standard 5 mm o.d. glass tubes. Chemical shifts are given relative to neat tetramethylsilane (1H, 13C) or neat CH3NO2 (14N, 15N). Raman spectra were recorded at ambient temperatures in Pyrex glass tubes in the range of 4000–80 cm-1 on a Bruker Equinox 55 FT-RA spectrometer using a Nd-YAG laser at 1064 nm or a Cary 83 spectrometer using an Ar laser at 488 nm. Infrared spectra were recorded in the range 4000-400 cm-1 on a Midac, M Series spectrometer using KBr pellets or on a Bruker Optics Alpha FT-IR ATR spectrometer. KBr pellets were prepared very carefully using an Econo mini-press (Barnes Engineering Co.). Differential thermal analysis (DTA) curves were recorded with a purge of dry nitrogen gas and a heating rate of 5 °C/min on an OZM Research DTA552-Ex instrument with the Meavy 2.2.0 software. The sample sizes were 3-15 mg. The impact and friction sensitivity data were determined with an OZM Research BAM Fall Hammer BFH-10 and an OZM Research BAM Friction apparatus FSKM-10, respectively, through five individual measurements that were averaged. Both instruments were calibrated using RDX. The samples were finely powdered materials that were not sifted.

X-ray Crystal Structure Determination

The single crystal X-ray diffraction data for HDNT-1, HDNT-2, 3, 3·4 (co-crystals), and 5·H2O were collected on a Bruker SMART diffractometer, equipped with an APEX CCD detector, using Mo K radiation (graphite monochromator) from a fine-focus tube. The single crystal X-ray diffraction data for the remaining structures were collected on a Bruker SMART APEX DUO diffractometer, equipped with an APEX II CCD detector, using Mo K radiation (TRIUMPH curved-crystal monochromator) from a fine-focus tube or Cu K from an IS micro-source. The frames were integrated using the SAINT algorithm to give the hkl files corrected for Lp/decay.2 The absorption correction was performed using the SADABS program.3 The structures were

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solved and refined on F2 using the Bruker SHELXTL Software Package.4-7 Non-hydrogen atoms were refined anisotropically. Structure drawings were prepared using the ORTEP-III for Windows V2.02 and Mercury 3.3.1 programs.8, 9 Further crystallographic details can be obtained from the Cambridge Crystallographic Data Centre (CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: (+44) 1223-336-033; e-mail: [email protected]) on quoting the deposition no. CCDC 1009538, 1013935-1013938 and 1045452, and from the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen, Germany (Fax: (+49) 7247-808-666, e-mail: [email protected], http://www.fiz-karlsruhe.de/request_for_deposited_data.html) on quoting the deposition numbers CSD 427861-427864.

Synthesis of potassium 3,5-dinitro-1,2,4-triazolate (method 1)

In a 2000 mL three-necked round-bottom flask, equipped with a reflux condenser, an addition funnel and a mechanical stirrer, a mixture of sodium nitrite (220 g, 3.28 mol) in water (350 mL) was heated to 50 °C using a water bath until all sodium nitrite had dissolved. A solution of 3,5-diamino-1,2,4-triazole (40.0 g, 0.404 mol) in water (500 mL) and concentrated sulfuric acid (36 mL) was added slowly and carefully through the addition funnel while the reaction mixture was stirred vigorously. Immediately, the reaction mixture turned red, foamed and formed some dark red precipitate. In addition, brown-orange fumes of nitric oxide were produced. After about one to two hours, the addition was completed and 80% sulfuric acid (220 mL) was added carefully while the reaction mixture was stirred vigorously in order to avoid excessive foam formation. The reaction mixture was then refluxed for about 60 minutes and then allowed to cool to 40-50 °C. Activated decolorizing charcoal (10 g) was added and the mixture stirred at ambient temperature for eight hours. The reaction mixture was then filtered over Celite 545 and the filtrate extracted six times with ethyl acetate (150 mL each). The combined organic phases were dried over magnesium sulphate and the solvent removed immediately using a rotary evaporator without (!) heating of the sample. The obtained yellow to orange oil or paste was dissolved immediately in acetone (200 mL) and the yellow solution poured onto potassium carbonate (60 g). Immediately, a gas was evolved and the mixture was stirred at ambient temperature. After about two hours, the mixture was filtered and the orange solid residue was washed extensively with acetone. The combined yellow filtrates were taken to dryness on a rotary evaporator leaving behind a yellow solid.Recrystallization from water resulted in the isolation of yellow crystals of KDNT·2H2O that were dried in vacuo at 50 °C for eight hours, resulting in colourless to pale yellow KDNT (yield: 52.5 g, 65.9 %). DTA: 265 °C decomposition; NMR (CD3CN) δ(ppm): 13C (125.76 MHz) 164.3 (C-NO2);14N (36.14 MHz) -20.3 (s, 1/2 = 65Hz, 2N, C-NO2), -52 (s, 1/2 = 500 Hz, DNT-).Raman (200 mW) ῦ/cm-1: 1545 (0.3), 1500 (0.2), 1425 (0.2), 1403 (10.0), 1388 (0.4), 1359 (1.6), 1310 (0.3), 1107 (0.3), 1100 (6.1), 1067 (0.1), 1028 (0.3), 834 (0.8), 769 (0.4), 515 (0.2). IR (ATR) ῦ/cm-1: 3604 (m), 3414 (m), 3327 (w), 3233 (w), 2749 (w), 2694 (w), 2663 (w), 2459 (w), 2144 (w), 1672 (w), 1643 (m), 1552 (w), 1536 (s), 1493 (s), 1440 (w), 1415 (w), 1388 (s), 1354

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(s), 1341 (w), 1299 (s), 1109 (m), 1100 (w), 1067 (w), 1050 (m), 997 (w), 877 (w), 846 (s), 835 (w), 770 (w), 749 (w), 684 (w), 648 (s), 605 (w), 515 (m), 502 (w), 483 (w), 472 (w), 457 (w), 404 (w).IR (AgCl pellet) ῦ/cm-1: 2757 (w), 2754 (w), 2748 (w), 2691 (w), 2658 (w), 2457 (m), 2399 (w), 2186 (w), 2158 (w), 2139 (w), 1563 (w), 1556 (s), 1540 (w), 1504 (s), 1439 (w), 1414 (m), 1392 (s), 1359 (s), 1343 (w), 1320 (w), 1310 (m), 1301 (s), 1296 (m), 1107 (w), 1100 (s), 1066 (w), 1050 (m), 1044 (m), 1019 (w), 850 (s), 837 (s), 831 (m), 771 (m), 768 (w), 652 (s), 606 (m), 519 (w), 515 (w).

Synthesis of potassium 3,5-dinitro-1,2,4-triazolate (method 2)

In a 1000 mL three-necked round-bottom flask that was cooled by a water bath, concentrated nitric acid (80 mL) was slowly added to hydrazine hydrate (20.0 g, 0.40 mol). Water (140 mL) and 2-cynaoguanidine (dicyandiamide) (33.6 g, 0.40 mol) was added and the reaction mixture heated to 50 °C for one hour. A solution of concentrated sulfuric acid (35 mL) in water (300 mL) was added, and the resulting DAT solution transferred into an addition funnel from which it was added carefully to a vigorously stirred solution of sodium nitrite (220 g, 3.28 mol) in water (350 mL) at 50 °C. After about one to two hours, the addition was completed and 80% sulfuric acid (220 mL) was added carefully while the reaction mixture was stirred vigorously in order to avoid excessive foam formation. The reaction mixture was then refluxed for about 60 minutes and then allowed to cool to 40-50 °C. Activated decolorizing charcoal (10 g) was added and the mixture stirred at ambient temperature for eight hours. The reaction mixture was then filtered over Celite 545 and the filtrate extracted six times with ethyl acetate (150 mL each). The combined organic phases were dried over magnesium sulphate and the solvent removed immediately using a rotary evaporator without (!) heating of the sample. The obtained yellow to orange oil or paste was dissolved immediately in acetone (200 mL) and the yellow solution poured onto potassium carbonate (60 g). Immediately, a gas was evolved and the mixture was stirred at ambient temperature. After about two hours, the mixture was filtered and the orange solid residue was washed extensively with acetone. The combined yellow filtrates were taken to dryness on a rotary evaporator leaving behind in a yellow-orange solid. Recrystallization from water resulted in the isolation of yellow crystals that were dried in vacuo at 50 °C for eight hours, resulting in yellow KDNT containing various impurities (yield: 54.3 g, 69% based on KDNT). IR (ATR) ῦ/cm-1: 2753 (vw), 2692 (vw), 2662 (vw), 2457 (vw), 2399 (vw), 2178 (vw), 2140 (m), 1553 (s), 1532 (s), 1494 (vs), 1413 (w), 1386 (vs), 1354 (vs), 1342 (s), 1296 (vs), 1099 (m), 1049 (m), 847 (vs), 835 (m), 787 (vw), 770 (w), 747 (vw), 730 (vw), 648 (s), 604 (m), 515 (w).

Synthesis of 3,5-dinitro-1H-1,2,4-triazole (HDNT)

A solution of KDNT (5.937 g, 30.11 mmol) in water (20 mL) was acidified with 20% sulfuric acid (50 mL) and the resulting yellow solution extracted four times with ethyl acetate (50 mL each). The combined organic phases were washed with water (50 mL), dried over magnesium

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sulphate and the solvent removed using a rotary evaporator. The resulting yellow oil was further dried in a high vacuum at 50-60 °C for eight hour, resulting in light-yellow, solid HDNT (yield: 4.502 g, 93.0%).HDNT of high-purity was obtained as a white solid through careful sublimation of the crude compound at 100-105 °C in a vacuum of less than 0.1 mTorr. The temperature was carefully monitored in order to avoid a potentially explosive decomposition of the HDNT.DTA: 170 °C (onset) explosive decomposition; Friction sensitivity: 144 N; Impact sensitivity: 35 J; NMR (CD3CN) δ(ppm): 1H (500.13 MHz) 13.6 (1/2 = 100 Hz); 13C (125.76 MHz) 157.1 (C-NO2);14N (36.14 MHz) -32.4 (s, 1/2 = 20 Hz C-NO2).Raman (50 mW) ῦ/cm-1: 2863 (0.2), 1581 (0.8), 1574 (1.0), 1528 (0.4), 1499 (0.7), 1487 (0.9), 1451 (2.6), 1436 (10.0), 1382 (3.4), 1366 (1.1), 1317 (0.8), 1280 (0.6), 1181 (1.2), 1163 (0.6), 1048 (1.0), 1043 (1.1), 1027 (0.3), 1012 (0.7), 1007 (0.8), 829 (0.9), 826 (1.3), 774 (0.4), 762 (0.8), 510 (0.6), 357 (1.1), 290 (1.0), 182 (0.7), 171 (0.7), 111 (2.5), 95 (2.4). IR (ATR, 20°C) ῦ/cm-1: 3039 (vw), 2992 (vw), 2934 (vw), 2883 (vw), 2839 (vw), 2802 (vw), 2748 (vw), 2639 (vw), 2557 (vw), 2162 (vw), 1698 (vw), 1563 (vs), 1530 (s sh), 1485 (s), 1430 (w), 1377 (s sh), 1363 (s sh), 1313 (vs), 1281 (m sh), 1174 (m), 1038 (m), 1023 (m sh), 1008 (m sh), 839 (vs), 825 (vs), 764 (vw), 730 (vw), 649 (m), 634 (m sh), 593 (m), 509 (m), 500 (m sh).

Synthesis of PPN+ 3,5-dinitro-1,2,4-triazolate [PPN][DNT]

[PPN][DNT] was prepared as described previously10 by adding an aqueous solution of HDNT to an aqueous solution of [PPN][Cl]. The resulting [PPN][DNT] precipitate was filtered, washed with water and recrystallized from acetone. In one occation, reddish crystals were obtained from the aqueous filtrate. These crystals were identified by X-ray diffraction as [PPN][H(AzNT)2] (AzNT = azidonitrotriazolate).The vibrational spectra of the isolated [PPN][DNT] exhibited vibrational bands due to azido compounds. An X-ray structural analysis of some of the crystals showed an substitutional disorder in which the about 25% of the DNT- anions were relaced by AzNT- anions.

Contaminated [PPN][DNT]: IR (ATR, 20°C) ῦ/cm-1: 3055 (w), 2122 (m), 1587 (w), 1531 (s), 1509 (w), 1480 (s), 1436 (s), 1423 (w), 1397 (w), 1373 (s), 1339 (m), 1325 (m), 1296 (w), 1281 (m), 1239 (vs), 1181 (w), 1162 (w), 1111 (s), 1073 (m), 1038 (w), 1024 (w), 997 (m), 932 (w), 858 (w), 838 (s), 828 (w), 803 (m), 760 (vw), 746 (s), 722 (vs), 690 (vs), 666 (vw), 616 (w), 597 (w), 553 (vs), 531 (w), 526 (vs), 498 (vs), 487 (w), 462 (w), 450 (w), 437 (w), 419 (vw). [PPN][H(AzNT)2]: IR (ATR, 20°C) ῦ/cm-1: 3063 (w), 2130 (s), 2017 (w), 1991 (vw), 1976 (w), 1896 (w), 1831 (vw), 1587 (w), 1573 (vw), 1556 (w), 1526 (m), 1479 (m), 1436 (m), 1383 (m), 1341 (w), 1294 (s), 1221 (w), 1183 (w), 1161 (w), 1113 (vs), 1024 (w), 1014 (w), 996 (m), 931 (vw), 839 (m), 793 (vw), 756 (vw), 749 (m), 721 (s), 690 (vs), 655 (w), 617 (vw), 549 (w), 528 (vs), 496 (s), 444 (m), 414 (vw).

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Crystallographic Information

Crystal Structure Report for the monoclinic modification HDNT-1

Figure S1: Asymmetric unit in the monoclinic modification HDNT-1.

Figure S3: Projection of the packing in the monoclinic modification HDNT-1 perpendicular to the 001 plane.

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Table S1: Sample and crystal data for the monoclinic modification HDNT-1.

Identification code HDNT-1

Chemical formula C2HN5O4

Formula weight 159.08 g/mol

Temperature 140(2) K

Wavelength 0.71073 Å

Crystal size 0.160 x 0.170 x 0.240 mm

Crystal habit clear colourless prism

Crystal system monoclinic

Space group P 1 21/c 1

Unit cell dimensions a = 6.1585(14) Å α = 90°

b = 9.083(2) Å β = 93.892(3)°

c = 9.858(2) Å γ = 90°

Volume 550.2(2) Å3

Z 4

Density (calculated) 1.920 g/cm3

Absorption coefficient 0.183 mm-1

F(000) 320

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Table S2: Data collection and structure refinement for the monoclinic modification HDNT-1.

Diffractometer Bruker SMART APEX

Radiation source fine-focus tube, MoKα

Theta range for data collection 3.05 to 29.48°

Index ranges -8

Table S3: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for the monoclinic modification HDNT-1.

U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

x/a y/b z/c U(eq)

C1 0.42794(17) 0.64736(11) 0.33762(10) 0.0183(2)

C2 0.14616(16) 0.75912(11) 0.35830(10) 0.0178(2)

N1 0.25254(15) 0.75125(10) 0.47970(9) 0.0199(2)

N2 0.44046(15) 0.67773(10) 0.46855(9) 0.0214(2)

N3 0.24980(14) 0.69417(9) 0.26293(8) 0.0179(2)

N4 0.59938(15) 0.56548(10) 0.27667(9) 0.0217(2)

N5 0.93865(15) 0.83445(10) 0.33730(9) 0.0217(2)

O1 0.56581(14) 0.53052(10) 0.15771(8) 0.0298(2)

O2 0.76453(13) 0.53841(9) 0.34885(9) 0.0288(2)

O3 0.85318(14) 0.83641(9) 0.22175(9) 0.0287(2)

O4 0.86729(15) 0.88799(10) 0.43873(9) 0.0333(2)

Table S1: Bond lengths (Å) for the monoclinic modification HDNT-1.

C1-N2 1.3169(14) C1-N3 1.3479(13)

C1-N4 1.4544(14) C2-N3 1.3118(13)

C2-N1 1.3267(13) C2-N5 1.4520(14)

N1-N2 1.3471(13) N1-H1 0.848(14)

N4-O1 1.2191(13) N4-O2 1.2260(13)

N5-O4 1.2204(13) N5-O3 1.2221(12)

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Table S1: Bond angles (°) for the monoclinic modification HDNT-1.

N2-C1-N3 117.43(9) N2-C1-N4 121.07(9)

N3-C1-N4 121.49(9) N3-C2-N1 112.82(9)

N3-C2-N5 125.17(9) N1-C2-N5 122.01(9)

C2-N1-N2 109.11(9) C2-N1-H1 129.9(9)

N2-N1-H1 120.9(9) C1-N2-N1 100.97(8)

C2-N3-C1 99.66(8) O1-N4-O2 125.87(10)

O1-N4-C1 116.76(9) O2-N4-C1 117.37(9)

O4-N5-O3 126.99(10) O4-N5-C2 115.68(9)

O3-N5-C2 117.33(9)

Table S1: Torsion angles (°) for the monoclinic modification HDNT-1.

N3-C2-N1-N2 0.31(12) N5-C2-N1-N2 -178.93(9)

N3-C1-N2-N1 -0.02(12) N4-C1-N2-N1 -179.57(9)

C2-N1-N2-C1 -0.16(11) N1-C2-N3-C1 -0.28(11)

N5-C2-N3-C1 178.92(10) N2-C1-N3-C2 0.18(12)

N4-C1-N3-C2 179.73(9) N2-C1-N4-O1 173.49(10)

N3-C1-N4-O1 -6.04(14) N2-C1-N4-O2 -6.84(15)

N3-C1-N4-O2 173.63(9) N3-C2-N5-O4 179.83(10)

N1-C2-N5-O4 -1.03(15) N3-C2-N5-O3 0.60(15)

N1-C2-N5-O3 179.74(9)

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Table S7: Anisotropic atomic displacement parameters (Å2) for the monoclinic modification HDNT-1.

The anisotropic atomic displacement factor exponent takes the form: -2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]

U11 U22 U33 U23 U13 U12

C1 0.0200(5) 0.0170(4) 0.0180(5) 0.0013(3) 0.0023(4) -0.0008(3)

C2 0.0195(5) 0.0177(4) 0.0163(4) 0.0007(3) 0.0014(4) -0.0018(4)

N1 0.0228(4) 0.0222(4) 0.0149(4) -0.0008(3) 0.0021(3) 0.0017(3)

N2 0.0222(4) 0.0229(4) 0.0190(4) 0.0008(3) 0.0004(3) 0.0015(3)

N3 0.0197(4) 0.0178(4) 0.0164(4) 0.0006(3) 0.0016(3) -0.0013(3)

N4 0.0221(4) 0.0173(4) 0.0263(5) 0.0016(3) 0.0060(4) -0.0009(3)

N5 0.0202(4) 0.0201(4) 0.0248(5) 0.0003(3) 0.0011(3) -0.0005(3)

O1 0.0330(5) 0.0320(5) 0.0254(4) -0.0067(3) 0.0082(3) 0.0023(3)

O2 0.0216(4) 0.0264(4) 0.0383(5) 0.0056(3) 0.0012(3) 0.0033(3)

O3 0.0269(4) 0.0300(4) 0.0279(4) 0.0024(3) -0.0068(3) 0.0007(3)

O4 0.0298(4) 0.0374(5) 0.0333(5) -0.0063(4) 0.0074(4) 0.0077(4)

Table S8: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for the monoclinic modification HDNT-1.

x/a y/b z/c U(eq)

H1 0.220(2) 0.7859(14) 0.5555(14) 0.021

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Crystal Structure Report for the triclinic modification HDNT-2

Figure S3: Asymmetric unit in the triclinic modification HDNT-2.

Figure S3: Projection of the packing in triclinic modification HDNT-2 perpendicular to the 001 plane.

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Figure S3: Projection of the packing in triclinic modification HDNT-2 perpendicular to the 010 plane.

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Figure S3: Projection of the packing in the triclinic modification HDNT-2 perpendicular to the 100 plane.

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Table S1: Sample and crystal data for the triclinic modification HDNT-2.

Identification code HDNT (2)

Chemical formula C2HN5O4





Crystal habit yellow prism

Crystal system triclinic

Space group P -1

Unit cell dimensions a = 8.7465(15) Å α = 111.927(2)°

b = 8.9684(16) Å β = 96.726(3)°

c = 11.942(2) Å γ = 93.853(2)°

Volume 856.7(3) Å3

Z 6



F(000) 480

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Table S1: Data collection and structure refinement for the triclinic modification HDNT-2.

Diffractometer Bruker SMART APEX



Index ranges -11

Table S1: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for the triclinic modification HDNT-2.


x/a y/b z/c U(eq)

C1 0.1191(3) 0.2092(3) 0.9249(2) 0.0222(5)

C2 0.1512(3) 0.0636(3) 0.7564(2) 0.0226(5)

C3 0.3735(3) 0.9278(3) 0.2248(2) 0.0223(5)

C4 0.2829(3) 0.7641(3) 0.2856(2) 0.0224(5)

C5 0.7108(3) 0.4226(3) 0.2417(2) 0.0236(5)

C6 0.7482(3) 0.5682(3) 0.4221(2) 0.0222(5)

N1 0.0992(2) 0.9634(2) 0.80550(18) 0.0239(4)

N2 0.0762(2) 0.0608(2) 0.91770(18) 0.0244(4)

N3 0.1675(2) 0.2197(2) 0.82722(19) 0.0255(4)

N4 0.1866(2) 0.0002(3) 0.63187(19) 0.0270(5)

N5 0.1151(2) 0.3496(2) 0.03625(19) 0.0284(5)

N6 0.4332(2) 0.7498(3) 0.2848(2) 0.0272(5)

N7 0.4955(2) 0.8584(3) 0.2447(2) 0.0286(5)

N8 0.2371(2) 0.8758(2) 0.24763(18) 0.0225(4)

N9 0.3905(2) 0.0555(2) 0.17867(19) 0.0273(5)

N10 0.1879(3) 0.6644(2) 0.32828(19) 0.0285(5)

N11 0.8602(2) 0.4744(2) 0.40833(18) 0.0229(4)

N12 0.8355(2) 0.3775(2) 0.28865(18) 0.0232(4)

N13 0.6497(2) 0.5414(2) 0.32162(18) 0.0234(4)

N14 0.6477(3) 0.3491(3) 0.11225(19) 0.0286(5)

N15 0.7375(3) 0.6926(2) 0.54036(19) 0.0275(5)

O1 0.1675(2) 0.4817(2) 0.03978(19) 0.0420(5)

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x/a y/b z/c U(eq)

O2 0.0590(2) 0.3250(2) 0.11746(17) 0.0368(5)

O3 0.1993(2) 0.0939(2) 0.58100(17) 0.0379(5)

O4 0.2025(3) 0.8566(2) 0.58912(18) 0.0433(5)

O5 0.2736(2) 0.1035(2) 0.14505(17) 0.0345(4)

O6 0.5233(2) 0.1058(3) 0.1775(2) 0.0482(6)

O7 0.0529(2) 0.6866(2) 0.3312(2) 0.0409(5)

O8 0.2527(2) 0.5661(2) 0.35924(18) 0.0400(5)

O9 0.5313(3) 0.3973(3) 0.07886(19) 0.0452(5)

O10 0.7177(2) 0.2439(2) 0.04853(17) 0.0365(5)

O11 0.6115(2) 0.7430(2) 0.55343(18) 0.0411(5)

O12 0.8541(2) 0.7362(2) 0.61537(17) 0.0367(5)

19

Table S1: Bond lengths (Å) for the triclinic modification HDNT-2.

C1-N3 1.320(3) C1-N2 1.326(3)

C1-N5 1.457(3) C2-N3 1.326(3)

C2-N1 1.327(3) C2-N4 1.459(3)

C3-N7 1.313(3) C3-N8 1.346(3)

C3-N9 1.451(3) C4-N8 1.312(3)

C4-N6 1.330(3) C4-N10 1.445(3)

C5-N12 1.324(3) C5-N13 1.329(3)

C5-N14 1.456(3) C6-N11 1.319(3)

C6-N13 1.325(3) C6-N15 1.454(3)

N1-N2 1.346(3) N1-H1 0.8472

N2-H1A 0.8476 N4-O3 1.214(3)

N4-O4 1.220(3) N5-O2 1.219(3)

N5-O1 1.225(3) N6-N7 1.346(3)

N6-H2 0.91(3) N9-O5 1.218(3)

N9-O6 1.221(3) N10-O7 1.213(3)

N10-O8 1.223(3) N11-N12 1.349(3)

N11-H3 0.8472 N12-H3A 0.8474

N14-O9 1.215(3) N14-O10 1.222(3)

N15-O12 1.211(3) N15-O11 1.224(3)

20

Table S1: Bond angles (°) for the triclinic modification HDNT-2.

N3-C1-N2 116.0(2) N3-C1-N5 123.1(2)

N2-C1-N5 120.8(2) N3-C2-N1 115.7(2)

N3-C2-N4 124.0(2) N1-C2-N4 120.2(2)

N7-C3-N8 118.0(2) N7-C3-N9 119.1(2)

N8-C3-N9 122.9(2) N8-C4-N6 113.3(2)

N8-C4-N10 126.4(2) N6-C4-N10 120.3(2)

N12-C5-N13 114.8(2) N12-C5-N14 122.3(2)

N13-C5-N14 122.9(2) N11-C6-N13 115.3(2)

N11-C6-N15 121.2(2) N13-C6-N15 123.5(2)

C2-N1-N2 104.63(19) C2-N1-H1 131.6

N2-N1-H1 123.6 C1-N2-N1 104.51(18)

C1-N2-H1A 131.7 N1-N2-H1A 123.6

C1-N3-C2 99.12(19) O3-N4-O4 126.0(2)

O3-N4-C2 117.8(2) O4-N4-C2 116.2(2)

O2-N5-O1 125.9(2) O2-N5-C1 116.9(2)

O1-N5-C1 117.3(2) C4-N6-N7 108.6(2)

C4-N6-H2 130.(2) N7-N6-H2 121.(2)

C3-N7-N6 101.04(19) C4-N8-C3 99.02(19)

O5-N9-O6 125.7(2) O5-N9-C3 118.3(2)

O6-N9-C3 116.0(2) O7-N10-O8 126.2(2)

O7-N10-C4 117.4(2) O8-N10-C4 116.3(2)

C6-N11-N12 104.90(19) C6-N11-H3 128.3

N12-N11-H3 126.6 C5-N12-N11 105.08(18)

C5-N12-H3A 132.3 N11-N12-H3A 122.5

C6-N13-C5 99.94(19) O9-N14-O10 126.8(2)

21

O9-N14-C5 117.1(2) O10-N14-C5 116.1(2)

O12-N15-O11 126.8(2) O12-N15-C6 116.8(2)

O11-N15-C6 116.5(2)

Table S1: Anisotropic atomic displacement parameters (Å2) for the triclinic modification HDNT-2.


U11 U22 U33 U23 U13 U12

C1 0.0205(12) 0.0227(11) 0.0229(12) 0.0078(10) 0.0032(9) 0.0060(9)

C2 0.0232(12) 0.0230(11) 0.0226(12) 0.0088(10) 0.0067(9) 0.0038(9)

C3 0.0242(12) 0.0224(11) 0.0206(12) 0.0083(10) 0.0035(9) 0.0033(9)

C4 0.0226(12) 0.0207(11) 0.0211(12) 0.0057(10) 0.0019(9) 0.0005(9)

C5 0.0296(13) 0.0194(11) 0.0223(12) 0.0085(10) 0.0044(10) 0.0020(9)

C6 0.0276(12) 0.0186(11) 0.0209(12) 0.0074(9) 0.0059(10) 0.0033(9)

N1 0.0280(11) 0.0227(10) 0.0212(10) 0.0081(8) 0.0056(8) 0.0037(8)

N2 0.0256(11) 0.0249(10) 0.0230(10) 0.0084(9) 0.0063(8) 0.0047(8)

N3 0.0254(11) 0.0232(10) 0.0264(11) 0.0073(9) 0.0060(9) 0.0020(8)

N4 0.0312(11) 0.0272(11) 0.0225(11) 0.0091(9) 0.0069(9) 0.0015(9)

N5 0.0295(11) 0.0252(11) 0.0261(11) 0.0046(9) 0.0050(9) 0.0047(9)

N6 0.0262(11) 0.0258(11) 0.0337(12) 0.0154(10) 0.0043(9) 0.0074(9)

N7 0.0268(11) 0.0289(11) 0.0325(12) 0.0139(10) 0.0060(9) 0.0054(9)

N8 0.0239(10) 0.0202(9) 0.0225(10) 0.0073(8) 0.0031(8) 0.0031(8)

N9 0.0306(12) 0.0239(10) 0.0272(11) 0.0094(9) 0.0059(9) 0.0016(9)

N10 0.0371(13) 0.0242(11) 0.0241(11) 0.0098(9) 0.0050(9) 0.0000(9)

N11 0.0260(10) 0.0223(10) 0.0219(10) 0.0089(8) 0.0064(8) 0.0054(8)

N12 0.0274(11) 0.0216(10) 0.0210(10) 0.0072(8) 0.0064(8) 0.0062(8)

22

U11 U22 U33 U23 U13 U12

N13 0.0282(11) 0.0211(10) 0.0212(10) 0.0078(8) 0.0044(8) 0.0064(8)

N14 0.0367(12) 0.0252(11) 0.0234(11) 0.0097(9) 0.0021(9) 0.0025(9)

N15 0.0380(13) 0.0205(10) 0.0237(11) 0.0069(9) 0.0080(9) 0.0060(9)

O1 0.0537(13) 0.0221(9) 0.0424(12) 0.0026(9) 0.0133(10) -0.0003(9)

O2 0.0452(12) 0.0372(11) 0.0286(10) 0.0093(9) 0.0159(9) 0.0115(9)

O3 0.0533(13) 0.0366(10) 0.0323(11) 0.0196(9) 0.0164(9) 0.0074(9)

O4 0.0725(15) 0.0251(10) 0.0305(11) 0.0058(8) 0.0172(10) 0.0068(9)

O5 0.0392(11) 0.0335(10) 0.0359(11) 0.0190(9) 0.0033(9) 0.0100(8)

O6 0.0339(11) 0.0530(13) 0.0729(16) 0.0420(13) 0.0101(11) -0.0024(9)

O7 0.0286(10) 0.0489(12) 0.0528(13) 0.0275(11) 0.0108(9) -0.0002(9)

O8 0.0556(13) 0.0307(10) 0.0414(12) 0.0226(9) 0.0065(10) 0.0066(9)

O9 0.0525(13) 0.0451(12) 0.0349(11) 0.0146(10) -0.0072(10) 0.0147(10)

O10 0.0450(12) 0.0346(10) 0.0242(10) 0.0042(8) 0.0067(8) 0.0055(9)

O11 0.0416(12) 0.0384(11) 0.0380(11) 0.0044(9) 0.0129(9) 0.0177(9)

O12 0.0443(12) 0.0309(10) 0.0267(10) 0.0044(8) -0.0018(9) 0.0012(9)

23

Table S1: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for the triclinic modification HDNT-2.

x/a y/b z/c U(eq)

H1 0.0881 -0.1390 0.7800 0.029

H1A 0.0367 0.0269 0.9666 0.029

H2 0.491(4) 0.678(4) 0.303(3) 0.047(9)

H3 0.9360 0.4782 0.4608 0.028

H3A 0.8901 0.3022 0.2582 0.028

24

Crystal Structure Report for (HDNT)3·4 H2O

Figure S3: Asymmetric unit in the crystal structure of (HDNT)3·4H2O.

25

Figure S3: Projection of the packing in (HDNT)3·4H2O perpendicular to the 001 plane.

26



27

Table S1: Sample and crystal data for (HDNT)3·4H2O.

Identification code HDNT_H2O

Chemical formula C6H11N15O16





Crystal habit yellow plate


Space group P 1

Unit cell dimensions a = 6.1906(2) Å α = 111.377(2)°

b = 9.5492(3) Å β = 93.467(2)°

c = 9.5656(3) Å γ = 90.765(3)°

Volume 525.22(3) Å3

Z 1



F(000) 280

28

Table S1: Data collection and structure refinement for (HDNT)3·4H2O.

Diffractometer Bruker APEX DUO



Index ranges -6


x/a y/b z/c U(eq)

C1 0.9293(6) 0.9115(4) 0.6904(4) 0.0136(9)

C2 0.7172(6) 0.7744(4) 0.5283(4) 0.0133(9)

C3 0.0758(6) 0.3001(4) 0.4741(4) 0.0135(9)

C4 0.3468(6) 0.1948(4) 0.5038(4) 0.0149(9)

C5 0.4031(6) 0.3647(4) 0.0471(4) 0.0147(9)

C6 0.6475(6) 0.3963(4) 0.9280(4) 0.0176(9)

N1 0.6163(5) 0.7962(3) 0.6523(3) 0.0156(8)

N2 0.7598(5) 0.8872(3) 0.7586(4) 0.0140(7)

N3 0.9118(5) 0.8428(3) 0.5439(4) 0.0154(7)

N4 0.1123(5) 0.0064(3) 0.7778(4) 0.0174(8)

N5 0.6157(5) 0.6782(3) 0.3837(4) 0.0184(8)

N6 0.3948(5) 0.3367(4) 0.5907(3) 0.0160(8)

N7 0.2141(5) 0.4035(4) 0.5676(4) 0.0143(8)

N8 0.1518(5) 0.1632(3) 0.4277(3) 0.0154(7)

N9 0.8674(5) 0.3371(4) 0.4237(4) 0.0168(8)

N10 0.5023(5) 0.0807(4) 0.4908(4) 0.0189(8)

N11 0.7028(5) 0.2722(4) 0.9495(3) 0.0198(8)

N12 0.5403(5) 0.2542(4) 0.0293(3) 0.0165(8)

N13 0.4631(5) 0.4590(4) 0.9841(3) 0.0170(8)

N14 0.2131(5) 0.3810(4) 0.1308(3) 0.0208(8)

N15 0.7860(6) 0.4664(5) 0.8520(4) 0.0279(9)

O1 0.2517(4) 0.0419(3) 0.7113(3) 0.0255(7)

O2 0.1117(4) 0.0419(3) 0.9147(3) 0.0236(7)

O3 0.7146(4) 0.6631(3) 0.2723(3) 0.0245(7)

30

x/a y/b z/c U(eq)

O4 0.4402(4) 0.6184(3) 0.3839(3) 0.0239(7)

O5 0.7521(4) 0.2357(3) 0.3333(3) 0.0226(7)

O6 0.8229(4) 0.4702(3) 0.4778(3) 0.0265(7)

O7 0.4635(4) 0.9572(3) 0.3904(3) 0.0261(7)

O8 0.6615(4) 0.1158(3) 0.5806(3) 0.0256(7)

O9 0.0916(4) 0.4813(3) 0.1332(3) 0.0290(7)

O10 0.1923(5) 0.2935(3) 0.1967(3) 0.0298(7)

O11 0.7375(5) 0.5895(4) 0.8521(4) 0.0408(9)

O12 0.9420(5) 0.3952(4) 0.7961(3) 0.0401(9)

O13 0.2194(4) 0.6897(3) 0.7210(3) 0.0181(6)

O14 0.3008(4) 0.7627(3) 0.0223(3) 0.0203(7)

O15 0.6257(4) 0.9699(3) 0.0403(3) 0.0192(7)

O16 0.9641(4) 0.8896(3) 0.2036(3) 0.0213(7)

31

Table S1: Bond lengths (Å) for (HDNT)3·4H2O.

C1-N3 1.309(5) C1-N2 1.329(5)

C1-N4 1.452(5) C2-N1 1.325(5)

C2-N3 1.336(5) C2-N5 1.451(5)

C3-N8 1.321(5) C3-N7 1.322(5)

C3-N9 1.443(5) C4-N6 1.324(5)

C4-N8 1.342(5) C4-N10 1.440(5)

C5-N13 1.313(5) C5-N12 1.332(5)

C5-N14 1.442(5) C5-C6 2.030(5)

C6-N11 1.320(5) C6-N13 1.344(5)

C6-N15 1.458(5) N1-N2 1.343(4)

N2-H1 0.90(4) N4-O1 1.216(4)

N4-O2 1.228(4) N5-O4 1.221(4)

N5-O3 1.225(4) N6-N7 1.341(4)

N7-H2 0.84(4) N9-O5 1.221(4)

N9-O6 1.228(4) N10-O8 1.225(4)

N10-O7 1.229(4) N11-N12 1.345(4)

N12-H3 0.90(4) N14-O9 1.221(4)

N14-O10 1.226(4) N15-O11 1.217(4)

N15-O12 1.223(5) O13-H1W 0.8817

O13-H2W 0.8726 O14-H3W 0.8622

O14-H4W 0.8721 O15-H5W 0.8658

O15-H6W 0.8707 O16-H7W 0.8718

O16-H8W 0.861

32

Table S1: Bond angles (°) for (HDNT)3·4H2O.

N3-C1-N2 113.9(3) N3-C1-N4 125.8(3)

N2-C1-N4 120.3(3) N1-C2-N3 117.3(3)

N1-C2-N5 119.6(3) N3-C2-N5 123.0(3)

N8-C3-N7 113.3(3) N8-C3-N9 124.2(3)

N7-C3-N9 122.4(3) N6-C4-N8 117.7(3)

N6-C4-N10 120.3(3) N8-C4-N10 122.1(3)

N13-C5-N12 112.8(3) N13-C5-N14 123.9(3)

N12-C5-N14 123.2(3) N13-C5-C6 40.7(2)

N12-C5-C6 72.1(2) N14-C5-C6 164.6(3)

N11-C6-N13 117.6(3) N11-C6-N15 121.2(4)

N13-C6-N15 121.2(4) N11-C6-C5 77.9(2)

N13-C6-C5 39.6(2) N15-C6-C5 160.6(3)

C2-N1-N2 101.6(3) C1-N2-N1 107.9(3)

C1-N2-H1 130.(2) N1-N2-H1 122.(2)

C1-N3-C2 99.3(3) O1-N4-O2 125.9(3)

O1-N4-C1 118.6(3) O2-N4-C1 115.5(3)

O4-N5-O3 125.8(3) O4-N5-C2 117.1(3)

O3-N5-C2 117.1(3) C4-N6-N7 101.1(3)

C3-N7-N6 108.9(3) C3-N7-H2 132.(3)

N6-N7-H2 119.(3) C3-N8-C4 99.0(3)

O5-N9-O6 126.0(3) O5-N9-C3 118.3(3)

O6-N9-C3 115.7(3) O8-N10-O7 125.9(3)

O8-N10-C4 117.0(3) O7-N10-C4 117.0(3)

C6-N11-N12 101.0(3) C5-N12-N11 108.9(3)

C5-N12-H3 131.(3) N11-N12-H3 120.(3)

33

C5-N13-C6 99.6(3) O9-N14-O10 126.0(3)

O9-N14-C5 118.0(3) O10-N14-C5 116.0(3)

O11-N15-O12 126.6(4) O11-N15-C6 117.4(4)

O12-N15-C6 116.0(4) H1W-O13-H2W 107.1

H3W-O14-H4W 111.5 H5W-O15-H6W 112.8

H7W-O16-H8W 109.1

Table S1: Anisotropic atomic displacement parameters (Å2) for (HDNT)3·4H2O.


U11 U22 U33 U23 U13 U12

C1 0.014(2) 0.012(2) 0.017(2) 0.0079(19) 0.0027(19) 0.0046(17)

C2 0.016(2) 0.011(2) 0.014(2) 0.0052(17) 0.0003(19) 0.0028(17)

C3 0.015(2) 0.015(2) 0.013(2) 0.0069(18) 0.0017(17) -0.0004(18)

C4 0.018(2) 0.016(2) 0.013(2) 0.0079(19) 0.0040(18) 0.0037(18)

C5 0.017(2) 0.014(2) 0.0105(19) 0.0007(18) 0.0021(17) -0.0011(18)

C6 0.021(2) 0.022(2) 0.010(2) 0.0069(18) -0.0004(18) -0.008(2)

N1 0.0161(18) 0.0113(18) 0.0169(19) 0.0029(15) -0.0040(16) -0.0002(15)

N2 0.0153(18) 0.0124(18) 0.0136(19) 0.0039(16) 0.0008(16) 0.0003(14)

N3 0.0161(18) 0.0138(17) 0.0169(19) 0.0061(15) 0.0013(14) 0.0036(15)

N4 0.0171(19) 0.0143(19) 0.018(2) 0.0027(15) -0.0003(16) 0.0009(15)

N5 0.023(2) 0.0120(18) 0.019(2) 0.0046(15) -0.0011(17) 0.0037(16)

N6 0.0154(19) 0.0179(19) 0.0173(18) 0.0088(16) 0.0038(14) 0.0030(15)

N7 0.0157(19) 0.0122(18) 0.0127(18) 0.0014(15) 0.0028(15) 0.0023(16)

N8 0.0160(18) 0.0152(19) 0.0158(18) 0.0061(15) 0.0034(15) 0.0024(15)

N9 0.016(2) 0.018(2) 0.0183(19) 0.0086(17) 0.0029(16) 0.0024(17)

N10 0.021(2) 0.017(2) 0.0199(19) 0.0082(17) 0.0023(17) 0.0046(16)

34

U11 U22 U33 U23 U13 U12

N11 0.0158(19) 0.027(2) 0.0150(19) 0.0061(16) 0.0032(16) -0.0049(16)

N12 0.0211(19) 0.0147(19) 0.0147(18) 0.0070(16) -0.0002(15) -0.0032(16)

N13 0.020(2) 0.0171(18) 0.0126(18) 0.0038(16) 0.0004(15) -0.0030(15)

N14 0.018(2) 0.024(2) 0.0123(19) -0.0016(17) 0.0005(15) -0.0073(17)

N15 0.025(2) 0.041(3) 0.017(2) 0.011(2) -0.0003(17) -0.010(2)

O1 0.0188(16) 0.0325(17) 0.0278(17) 0.0141(15) 0.0054(14) -0.0060(13)

O2 0.0243(16) 0.0253(16) 0.0163(17) 0.0025(13) -0.0021(13) -0.0029(13)

O3 0.0328(17) 0.0243(17) 0.0128(17) 0.0024(13) 0.0035(14) 0.0018(13)

O4 0.0190(16) 0.0237(16) 0.0258(17) 0.0064(13) -0.0044(13) -0.0048(13)

O5 0.0212(16) 0.0243(16) 0.0194(16) 0.0052(14) -0.0027(13) -0.0024(13)

O6 0.0267(17) 0.0174(18) 0.0330(18) 0.0064(14) -0.0007(14) 0.0080(13)

O7 0.0324(18) 0.0173(17) 0.0237(17) 0.0017(15) -0.0008(14) 0.0046(14)

O8 0.0203(16) 0.0255(17) 0.0305(17) 0.0109(14) -0.0067(15) 0.0031(13)

O9 0.0182(16) 0.0348(18) 0.0260(17) 0.0014(14) 0.0025(13) 0.0048(15)

O10 0.0374(19) 0.0320(18) 0.0199(16) 0.0087(15) 0.0087(14) -0.0097(15)

O11 0.051(2) 0.039(2) 0.043(2) 0.0284(18) -0.0010(17) -0.0151(17)

O12 0.0263(19) 0.066(2) 0.0266(18) 0.0137(17) 0.0092(16) -0.0033(17)

O13 0.0179(14) 0.0193(15) 0.0174(15) 0.0070(12) 0.0028(12) 0.0003(11)

O14 0.0261(17) 0.0157(15) 0.0198(15) 0.0068(13) 0.0041(13) 0.0057(12)

O15 0.0191(15) 0.0202(15) 0.0183(15) 0.0077(12) -0.0015(12) -0.0030(12)

O16 0.0261(16) 0.0150(15) 0.0215(16) 0.0059(13) -0.0007(13) -0.0038(12)

Table S1: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for (HDNT)3·4H2O.

x/a y/b z/c U(eq)

35

x/a y/b z/c U(eq)

H1 0.734(6) 0.921(4) 0.857(5) 0.017

H2 0.202(6) 0.495(5) 0.617(5) 0.017

H3 0.540(6) 0.177(5) 0.062(4) 0.02

H1W 0.2339 0.7069 0.8181 0.022

H2W 0.3400 0.7209 0.6972 0.022

H3W 0.1970 0.7984 0.0798 0.024

H4W 0.3336 0.6734 0.0200 0.024

H5W 0.7322 0.9661 0.1015 0.023

H6W 0.5199 0.9059 0.0324 0.023

H7W 0.9224 0.8281 0.2461 0.026

H8W 1.0047 0.9747 0.2723 0.026

36

Crystal Structure Report for 5-ethoxy-1-methyl-3-nitro-1H-1,2,4-triazole 1

Figure S3: Asymmetric unit in the crystal structure of 5-ethoxy-1-methyl-3-nitro-1H-1,2,4-triazole 1.

Figure S1: Projection of the packing in 1 perpendicular to the 001 plane.

37



38

Table S23: Data collection and structure refinement for 1.

Identification code cu_usc01_0m

Empirical formula C5H8N4O3

Formula weight 172.15

Temperature/K 100.15


Space group P-1

a/Å 6.6336(8)

b/Å 7.6993(8)

c/Å 8.5129(9)

α/° 83.636(5)

β/° 73.035(5)

γ/° 65.784(6)

Volume/Å3 379.25(7)

Z 2

ρcalcg/cm3 1.508

μ/mm-1 1.086

F(000) 180.0

Crystal size/mm3 0.203 × 0.056 × 0.041

Radiation CuKα (λ = 1.54178)

2Θ range for data collection/° 10.866 to 135.894

Index ranges -7 ≤ h ≤ 7, -9 ≤ k ≤ 9, -10 ≤ l ≤ 10

Reflections collected 8069

Independent reflections 1315 [Rint = 0.0241, Rsigma = 0.0145]

Data/restraints/parameters 1315/0/141

Goodness-of-fit on F2 1.055

Final R indexes [I>=2σ (I)] R1 = 0.0300, wR2 = 0.0823

Final R indexes [all data] R1 = 0.0321, wR2 = 0.0841

Largest diff. peak/hole / e Å-3 0.20/-0.16

39

Table S1: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for 1.

Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.

Atom x y z U(eq)

N1 2032.8(17) 5842.1(14) 5921.9(13) 24.6(3)

N2 3402.2(17) 3377.2(15) 4245.8(13) 24.0(3)

N3 3587.5(17) 2594.0(15) 5741.5(13) 25.0(3)

N4 2661.0(18) 3969.5(15) 8385.4(14) 27.6(3)

O1 2174.3(15) 6343.0(12) 3079.9(11) 27.5(2)

O2 2060.9(18) 5439.6(14) 9139.9(12) 36.4(3)

O3 3219.9(17) 2364.0(13) 8965.2(12) 34.8(3)

C1 2746(2) 4129.9(17) 6650.5(15) 23.6(3)

C2 2487(2) 5288.3(17) 4391.1(15) 23.5(3)

C3 1138(2) 8406.4(17) 3373.1(17) 27.0(3)

C4 859(3) 9344(2) 1774.5(19) 34.3(3)

C5 4190(3) 2228(2) 2762.3(17) 30.7(3)

40

Table S25: Anisotropic Displacement Parameters (Å2×103) for 1.

The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].

Atom U11 U22 U33 U23 U13 U12

N1 21.9(5) 22.9(5) 28.8(6) -0.6(4) -7.3(4) -8.2(4)

N2 23.2(5) 20.6(5) 28.2(6) -0.1(4) -8.3(4) -7.7(4)

N3 22.7(5) 23.1(5) 29.4(6) 2.2(4) -8.3(4) -9.1(4)

N4 26.3(5) 26.9(6) 28.9(6) 1.1(4) -6.3(4) -11.1(4)

O1 31.4(5) 19.7(5) 29.6(5) 0.4(4) -11.5(4) -6.4(4)

O2 46.3(6) 32.6(5) 30.3(5) -4.1(4) -7.6(4) -16.6(4)

O3 41.4(6) 29.2(5) 32.4(5) 6.8(4) -12.6(4) -12.6(4)

C1 20.0(6) 23.4(6) 27.7(7) 0.4(5) -6.6(5) -8.8(5)

C2 19.9(6) 21.2(6) 29.8(7) 1.7(5) -8.5(5) -7.8(5)

C3 26.3(6) 19.0(6) 35.1(7) -0.7(5) -10.8(6) -6.6(5)

C4 36.7(8) 24.8(7) 40.8(8) 3.5(6) -16.7(7) -8.3(6)

C5 34.8(7) 23.7(7) 31.2(7) -2.8(5) -7.7(6) -9.4(6)

Table S25: Bond Lengths for 1.

Atom Atom Length/Å Atom Atom Length/Å

N1 C1 1.3508(16) N4 O2 1.2225(15)

N1 C2 1.3264(16) N4 O3 1.2266(15)

N2 N3 1.3640(15) N4 C1 1.4548(17)

N2 C2 1.3464(16) O1 C2 1.3208(16)

N2 C5 1.4607(17) O1 C3 1.4665(15)

N3 C1 1.3108(16) C3 C4 1.4922(19)

41

Table S27: Bond Angles for 1.

Atom Atom Atom Angle/˚ Atom Atom Atom Angle/˚

C2 N1 C1 100.08(10) C2 O1 C3 115.20(10)

N3 N2 C5 122.68(10) N1 C1 N4 121.55(11)

C2 N2 N3 109.13(10) N3 C1 N1 118.24(12)

C2 N2 C5 128.16(11) N3 C1 N4 120.19(11)

C1 N3 N2 100.86(10) N1 C2 N2 111.70(11)

O2 N4 O3 125.45(12) O1 C2 N1 128.84(11)

O2 N4 C1 117.44(11) O1 C2 N2 119.46(11)

O3 N4 C1 117.11(11) O1 C3 C4 107.27(11)

Table S27: Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 1.

Atom x y z U(eq)

H3A 2160(30) 8710(20) 3803(18) 26(4)

H3B -330(30) 8690(20) 4205(18) 25(4)

H4A 2320(30) 9010(20) 970(20) 43(5)

H4B 130(30) 10710(20) 1940(20) 38(4)

H4C -130(30) 8930(20) 1380(20) 44(5)

H5A 5370(40) 2530(30) 1990(30) 64(6)

H5B 2900(40) 2470(30) 2370(30) 61(6)

H5C 4830(30) 920(30) 3080(20) 45(5)

42

Crystal Structure Report for 1-acetyl-3,5-diamino-1H-1,2,4-triazole 2


43


44


45

Table S29: Sample and crystal data for 2.

Identification code AcDNTChemical formula C4H7N5OFormula weight 141.15Temperature 100(2) KWavelength 0.71073 ÅCrystal system triclinicSpace group P -1Unit cell dimensions a = 5.25150(10) Å α = 67.2290(10)°

b = 7.69060(10) Å β = 85.4460(10)°c = 8.49150(10) Å γ = 70.1300(10)°

Volume 296.854(8) Å3Z 2Density (calculated) 1.579 g/cm3Absorption coefficient 0.122 mm-1F(000) 148

46

Table S30: Data collection and structure refinement for 2.Diffractometer Bruker APEX DUORadiation source fine-focus tube, MoKα Theta range for data collection 2.61 to 36.40°

Index ranges -8



x/a y/b z/c U(eq)

C1 0.60431(9) 0.71334(6)0.00221(6)

0.00969(8)

C2 0.26754(9) 0.71975(6)0.15887(6)

0.00974(8)

C3 0.46799(9) 0.37198(7)0.37460(6)

0.01160(8)

C4 0.71507(10)0.19034(7)

0.41216(6)

0.01504(9)

N1 0.46568(8) 0.53332(6)0.22513(5)

0.01016(7)

N2 0.68752(8) 0.53103(6)0.12133(5)

0.01038(8)

N3 0.34994(8) 0.83553(6)0.01797(5)

0.01059(8)

N4 0.75134(9) 0.77978(6)0.86564(5)

0.01257(8)

N5 0.03272(9) 0.77609(6)0.22891(5)

0.01256(8)

O1 0.27708(9) 0.38638(6)0.46664(5)

0.01712(9)

Table S25: Bond lengths (Å) for 2.

C1-N2 1.3174(6) C1-N4 1.3673(6)C1-N3 1.3788(6) C2-N3 1.3292(6)C2-N5 1.3349(6) C2-N1 1.3818(6)C3-O1 1.2228(6) C3-N1 1.3870(6)C3-C4 1.4918(7) C4-H4A 0.98C4-H4B 0.98 C4-H4C 0.98N1-N2 1.4034(6) N4-H1 0.876(12)N4-H2 0.898(12) N5-H3 0.904(12)N5-H4 0.863(11)

48

Table S26: Bond angles (°) for 2.

N2-C1-N4 123.45(4) N2-C1-N3 116.03(4)N4-C1-N3 120.47(4) N3-C2-N5 125.37(4)N3-C2-N1 109.63(4) N5-C2-N1 124.97(4)O1-C3-N1 119.86(4) O1-C3-C4 124.58(4)N1-C3-C4 115.55(4) C3-C4-H4A 109.5C3-C4-H4B 109.5 H4A-C4-H4B 109.5C3-C4-H4C 109.5 H4A-C4-H4C 109.5H4B-C4-H4C 109.5 C2-N1-C3 128.45(4)C2-N1-N2 109.02(4) C3-N1-N2 122.40(4)C1-N2-N1 101.90(4) C2-N3-C1 103.41(4)C1-N4-H1 113.0(8) C1-N4-H2 116.7(7)H1-N4-H2 113.2(11) C2-N5-H3 117.0(8)C2-N5-H4 119.5(7) H3-N5-H4 119.9(10)

Table S27: Anisotropic atomic displacement parameters (Å2) for 2.


U11 U22 U33 U23 U13 U12C1 0.00867(16) 0.00909(16) 0.01027(16) -0.00318(13) 0.00112(12) -0.00249(12)C2 0.00866(16) 0.00898(16) 0.01040(16) -0.00362(13) 0.00075(12) -0.00172(12)C3 0.01124(17) 0.01072(17) 0.00960(16) -0.00205(13) 0.00106(13) -0.00205(13)C4 0.01308(19) 0.01184(18) 0.01321(18) -0.00114(14) 0.00021(14) 0.00006(14)

N1 0.00870(15) 0.00889(14) 0.00962(14) -0.00207(11) 0.00177(11) -0.00103(11)

N2 0.00860(15) 0.00976(15) 0.01031(15) -0.00268(12) 0.00205(11) -0.00180(11)

N3 0.00884(15) 0.00879(15) 0.01191(15) -0.00285(12) 0.00177(11) -0.00184(11)

N4 0.01102(16) 0.01098(16) 0.01277(16) -0.00228(12) 0.00366(12) -0.00344(12)

N5 0.00957(15) 0.01184(16) 0.01254(16) -0.00354(13) 0.00285(12) -0.00094(12)

O1 0.01486(17) 0.01649(17) 0.01351(16) -0.00254(13) 0.00584(12) -0.00233(13)

49

Table S28: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for 2.

x/a y/b z/c U(eq)H4A 0.6917 0.0818 0.5147 0.023H4B 0.8733 0.2213 0.4315 0.023H4C 0.7425 0.1486 0.3149 0.023H1 0.735(2) 0.9058(18) -0.1643(15) 0.028(3)H2 0.923(2) 0.7007(17) -0.1315(14) 0.024(2)H3 -0.096(2) 0.8906(18) 0.1635(15) 0.029(3)H4 -0.013(2) 0.6884(17) 0.3146(14) 0.023(2)

50

Crystal Structure Report for 1-(i-propyl)-3,5-dinitro-1H-1,2,4-triazole 3

Figure S20: Asymmetric unit in the crystal structure of 3.


51



52


Identification code HDNTimpurityChemical formula C5H7N5O4Formula weight 201.16Temperature 130(2) KWavelength 0.71073 ÅCrystal size 0.180 x 0.210 x 0.260 mmCrystal habit clear pale yellow prismCrystal system orthorhombicSpace group P b c aUnit cell dimensions a = 9.4402(19) Å α = 90°

b = 10.611(2) Å β = 90°c = 17.296(4) Å γ = 90°


53


Diffractometer Bruker SMART APEXRadiation source fine-focus tube, MoKα Theta range for data collection 2.36 to 28.57°

Index ranges -12

Table S31: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for 3.U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.

x/a y/b z/c U(eq)

C1 0.32659(16)0.09436(14) 0.33996(9)

0.0289(3)

C2 0.46877(16)0.21658(14) 0.29449(9)

0.0283(3)

C3 0.65767(17)0.19786(17)

0.40377(10)

0.0370(4)

C4 0.7329(2) 0.07375(19)0.41323(11)

0.0490(5)

C5 0.6259(2) 0.2637(2) 0.47975(11)0.0494(5)

N1 0.52142(13)0.17584(12) 0.36226(7)

0.0290(3)

N2 0.42717(13)0.09428(13) 0.39278(8)

0.0317(3)

N3 0.34515(14)0.16716(12) 0.27788(7)

0.0306(3)

N4 0.20218(14)0.01512(13) 0.34775(8)

0.0350(3)

N5 0.53883(15)0.30410(13) 0.24215(8)

0.0358(3)

O1 0.11097(13)0.02530(13) 0.29827(8)

0.0497(4)

O2 0.19808(14)0.94151(14) 0.40175(8)

0.0538(4)

O3 0.49434(16)0.30828(14) 0.17630(8)

0.0589(4)

O4 0.63671(13)0.36692(11) 0.26755(7)

0.0412(3)

Table S32: Bond lengths (Å) for 3.C1-N2 1.318(2) C1-N3 1.334(2)C1-N4 1.451(2) C2-N3 1.311(2)C2-N1 1.345(2) C2-N5 1.456(2)C3-N1 1.491(2) C3-C4 1.505(3)C3-C5 1.518(2) C3-H3 1.0C4-H4A 0.98 C4-H4B 0.98C4-H4C 0.98 C5-H5A 0.98C5-H5B 0.98 C5-H5C 0.98N1-N2 1.3488(18) N4-O2 1.2182(19)

55

N4-O1 1.2188(18) N5-O3 1.2147(19)N5-O4 1.2211(18)

56

Table S40: Bond angles (°) for 3.N2-C1-N3 117.62(14) N2-C1-N4 121.24(14)N3-C1-N4 121.11(14) N3-C2-N1 113.05(14)N3-C2-N5 121.54(14) N1-C2-N5 125.39(14)N1-C3-C4 108.78(14) N1-C3-C5 108.55(14)C4-C3-C5 113.71(15) N1-C3-H3 108.6C4-C3-H3 108.6 C5-C3-H3 108.6C3-C4-H4A 109.5 C3-C4-H4B 109.5H4A-C4-H4B 109.5 C3-C4-H4C 109.5H4A-C4-H4C 109.5 H4B-C4-H4C 109.5C3-C5-H5A 109.5 C3-C5-H5B 109.5H5A-C5-H5B 109.5 C3-C5-H5C 109.5H5A-C5-H5C 109.5 H5B-C5-H5C 109.5C2-N1-N2 107.67(12) C2-N1-C3 133.48(13)N2-N1-C3 118.75(13) C1-N2-N1 101.75(13)C2-N3-C1 99.91(13) O2-N4-O1 124.94(14)O2-N4-C1 117.95(14) O1-N4-C1 117.09(14)O3-N5-O4 125.38(15) O3-N5-C2 116.70(14)O4-N5-C2 117.92(14)

57

Table S34: Anisotropic atomic displacement parameters (Å2) for 3.

The anisotropic atomic displacement factor exponent takes the form: -2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]U11 U22 U33 U23 U13 U12

C1 0.0322(8) 0.0264(8) 0.0281(8) -0.0024(6) 0.0002(6) 0.0012(6)C2 0.0345(8) 0.0238(7) 0.0267(8) -0.0023(6) 0.0025(6) 0.0036(6)C3 0.0329(8) 0.0447(10) 0.0334(8) 0.0003(7) -0.0059(7) -0.0061(7)C4 0.0458(10) 0.0585(13) 0.0427(11) -0.0035(9) -0.0082(8) 0.0113(9)C5 0.0560(11) 0.0470(11) 0.0453(11) -0.0130(9) -0.0142(9) 0.0000(9)N1 0.0311(7) 0.0287(7) 0.0273(6) -0.0016(5) 0.0004(5) -0.0012(5)N2 0.0343(7) 0.0319(7) 0.0288(7) 0.0006(6) 0.0006(5) -0.0033(6)N3 0.0354(7) 0.0254(7) 0.0310(7) -0.0011(5) -0.0015(5) 0.0035(5)N4 0.0352(7) 0.0331(8) 0.0367(8) -0.0015(6) -0.0012(6) -0.0020(6)N5 0.0434(8) 0.0252(7) 0.0389(8) 0.0027(6) 0.0048(6) 0.0030(6)O1 0.0376(7) 0.0471(8) 0.0645(9) 0.0072(7) -0.0163(6) -0.0040(6)O2 0.0560(8) 0.0610(9) 0.0444(7) 0.0161(7) -0.0039(6) -0.0204(7)O3 0.0865(11) 0.0561(9) 0.0342(7) 0.0157(6) -0.0062(7) -0.0157(8)O4 0.0374(6) 0.0298(6) 0.0563(8) 0.0048(6) 0.0035(6) -0.0009(5)

58

TableS35: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for 3.

x/a y/b z/c U(eq)

H3 0.7182 0.2546 0.3715 0.044H4A 0.8259 0.0880 0.4368 0.073H4B 0.7450 0.0341 0.3625 0.073H4C 0.6766 0.0183 0.4466 0.073H5A 0.7149 0.2829 0.5064 0.074H5B 0.5677 0.2086 0.5123 0.074H5C 0.5744 0.3422 0.4695 0.074

59

Crystal Structure Report for the co-crystal of 1-(i-propyl)-3,5-dinitro-1H-1,2,4-triazole and 3-nitro-1H-1,2,4-triazole 3·4.

Figure S24: Asymmetric unit in the crystal structure of 3·4.

60

Figure S20: Projection of the packing in 3·4 perpendicular to the 100 plane.

61


62


Table S36: Sample and crystal data for 3·4.Identification code HDNTimpurity2Chemical formula C7H9N9O6Formula weight 315.23Temperature 130(2) KWavelength 0.71073 ÅCrystal size 0.130 x 0.220 x 0.270 mmCrystal habit clear pale yellow prismCrystal system orthorhombicSpace group P b c aUnit cell dimensions a = 9.472(2) Å α = 90°

b = 11.272(2) Å β = 90°c = 23.860(5) Å γ = 90°

Volume 2547.5(9) Å3Z 8

63

Density (calculated) 1.644 g/cm3Absorption coefficient 0.144 mm-1F(000) 1288

64

Table S37: Data collection and structure refinement for 3·4.


Index ranges -12

Table S38: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for 3·4


x/a y/b z/c U(eq)

C1 0.4690(2)0.54038(19)

0.28211(9)0.0325(5)

C2 0.3362(2)0.66278(19)

0.31512(9)0.0318(5)

C3 0.6759(2) 0.5700(2)0.35162(10)

0.0384(5)

C4 0.7497(3) 0.6874(3)0.36041(12)

0.0500(7)

C5 0.6581(3) 0.4979(3)0.40337(11)

0.0483(6)

C6 0.9627(2)0.27222(18)

0.49235(8)0.0260(4)

C7 0.1138(2)0.38134(19)

0.46324(9)0.0312(5)

N1 0.3429(2)0.58454(17)

0.27330(8)0.0346(4)

N20.53433(19)

0.58962(16)

0.32626(8)0.0316(4)

N3 0.4470(2)0.67112(16)

0.34864(8)0.0339(4)

N4 0.5290(2)0.44914(18)

0.24604(9)0.0404(5)

N5 0.2135(2)0.73776(18)

0.32244(8)0.0382(5)

N60.18120(19)

0.29214(18)

0.48784(8)0.0358(4)

N7 0.0808(2)0.22207(18)

0.50604(9)0.0398(5)

N80.97599(19)

0.37352(18)

0.46515(8)0.0373(5)

N9 0.1881(2)0.48022(18)

0.43829(9)0.0424(5)

O10.62673(18)

0.39039(15)

0.26430(8)0.0472(5)

66

x/a y/b z/c U(eq)

O2 0.4762(2) 0.4383(2) 0.20024(9)0.0674(7)

O3 0.2170(2)0.81272(17)

0.35900(8)0.0522(5)

O40.11397(19)

0.72067(19)

0.29115(8)0.0551(5)

O5 0.3150(2)0.48409(18)

0.44612(9)0.0576(6)

O6 0.1178(2)0.55195(17)

0.41181(9)0.0620(6)

67

Table S39: Bond lengths (Å) for 3·4.

C1-N1 1.311(3) C1-N2 1.342(3)C1-N4 1.456(3) C2-N3 1.323(3)C2-N1 1.333(3) C2-N5 1.448(3)C3-N2 1.487(3) C3-C5 1.488(3)C3-C4 1.511(4) C3-H3 1.0C4-H4A 0.98 C4-H4B 0.98C4-H4C 0.98 C5-H5A 0.98C5-H5B 0.98 C5-H5C 0.98C6-N7 1.295(3) C6-N8 1.320(3)C6-H6 0.95 C7-N6 1.328(3)C7-N9 1.446(3) N2-N3 1.346(3)N4-O2 1.208(3) N4-O1 1.219(3)N5-O3 1.215(3) N5-O4 1.218(3)N6-N7 1.310(3) N7-H7 0.88N9-O5 1.217(3) N9-O6 1.223(3)

68

Table S40: Bond angles (°) for 3·4.

N1-C1-N2 112.9(2) N1-C1-N4 121.9(2)N2-C1-N4 125.2(2) N3-C2-N1 117.5(2)N3-C2-N5 121.5(2) N1-C2-N5 120.98(19)N2-C3-C5 108.5(2) N2-C3-C4 110.1(2)C5-C3-C4 114.5(2) N2-C3-H3 107.8C5-C3-H3 107.8 C4-C3-H3 107.8C3-C4-H4A 109.5 C3-C4-H4B 109.5H4A-C4-H4B 109.5 C3-C4-H4C 109.5H4A-C4-H4C 109.5 H4B-C4-H4C 109.5C3-C5-H5A 109.5 C3-C5-H5B 109.5H5A-C5-H5B 109.5 C3-C5-H5C 109.5H5A-C5-H5C 109.5 H5B-C5-H5C 109.5N7-C6-N8 114.81(19) N7-C6-H6 122.6N8-C6-H6 122.6 N6-C7-N9 122.1(2)C1-N1-C2 100.04(18) C1-N2-N3 108.10(18)C1-N2-C3 132.33(19) N3-N2-C3 119.57(18)C2-N3-N2 101.47(18) O2-N4-O1 125.7(2)O2-N4-C1 116.4(2) O1-N4-C1 118.0(2)O3-N5-O4 124.9(2) O3-N5-C2 118.07(19)O4-N5-C2 117.1(2) N7-N6-C7 104.73(18)C6-N7-N6 106.26(19) C6-N7-H7 126.9N6-N7-H7 126.9 O5-N9-O6 126.4(2)O5-N9-C7 116.4(2) O6-N9-C7 117.2(2)

69

Table S41: Anisotropic atomic displacement parameters (Å2) for 3·4.


U11 U22 U33 U23 U13 U12C1 0.0349(11) 0.0307(10) 0.0317(11) 0.0009(9) -0.0005(9) -0.0020(9)C2 0.0332(11) 0.0324(10) 0.0297(10) 0.0031(8) -0.0031(9) -0.0016(9)C3 0.0292(11) 0.0482(13) 0.0379(12) -0.0003(10) -0.0010(9) 0.0019(10)C4 0.0387(13) 0.0640(17) 0.0473(14) -0.0054(13) -0.0014(11) -0.0120(13)C5 0.0473(14) 0.0549(15) 0.0426(14) 0.0088(12) -0.0064(11) 0.0088(13)C6 0.0157(9) 0.0304(10) 0.0319(10) -0.0003(8) 0.0007(7) -0.0017(7)C7 0.0289(10) 0.0343(10) 0.0305(11) -0.0036(9) 0.0002(8) 0.0002(9)N1 0.0357(10) 0.0335(9) 0.0345(10) -0.0002(8) -0.0032(8) -0.0001(8)N2 0.0291(9) 0.0351(9) 0.0306(9) 0.0022(8) -0.0007(7) -0.0012(8)N3 0.0332(10) 0.0370(10) 0.0315(10) -0.0005(8) -0.0002(8) 0.0003(8)N4 0.0393(11) 0.0369(10) 0.0451(11) -0.0030(9) 0.0000(9) -0.0003(9)N5 0.0378(11) 0.0401(10) 0.0368(10) -0.0015(9) -0.0034(8) 0.0040(9)N6 0.0266(9) 0.0408(10) 0.0399(10) 0.0026(8) -0.0011(8) 0.0009(8)N7 0.0364(11) 0.0383(10) 0.0447(11) 0.0079(9) 0.0025(9) 0.0017(9)N8 0.0273(9) 0.0408(10) 0.0439(11) 0.0007(9) -0.0007(8) 0.0028(8)N9 0.0478(13) 0.0395(10) 0.0401(11) -0.0045(9) 0.0100(9) -0.0053(10)O1 0.0412(10) 0.0382(9) 0.0621(12) -0.0013(8) -0.0025(8) 0.0053(7)O2 0.0763(15) 0.0741(15) 0.0519(12) -0.0286(11) -0.0168(11) 0.0240(12)O3 0.0534(12) 0.0540(11) 0.0493(11) -0.0156(9) -0.0061(9) 0.0118(9)O4 0.0396(10) 0.0657(13) 0.0601(12) -0.0152(10) -0.0188(9) 0.0126(9)O5 0.0469(11) 0.0620(12) 0.0638(13) -0.0093(10) 0.0106(9) -0.0223(10)O6 0.0799(15) 0.0460(10) 0.0602(12) 0.0166(10) 0.0121(11) 0.0056(10)

70

Table S42: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for 3·4.

x/a y/b z/c U(eq)H3 0.7333 0.5226 0.3245 0.046H4A 0.6957 0.7355 0.3870 0.075H4B 0.7566 0.7294 0.3246 0.075H4C 0.8446 0.6733 0.3753 0.075H5A 0.6113 0.4229 0.3940 0.072H5B 0.6004 0.5419 0.4304 0.072H5C 0.7509 0.4815 0.4198 0.072H6 -0.1265 0.2387 0.5012 0.031H7 0.0915 0.1545 0.5240 0.048

71

Crystal Structure Report for sodium 3-nitro-1,2,4-triazol-5-olate monohydrate 5·H2O

Figure S31: Asymmetric unit in the crystal structure of 5·H2O.

Figure S32: Projection of the packing in 5·H2O down the a-axis.

72

Figure S27: Projection of the packing in 5·H2O down the b-axis.

73

Figure S28: Projection of the packing in 5·H2O down the c-axis.

Table S51: Sample and crystal data for 5·H2O.Identification code DNTimpurityChemical formula C2H3N4NaO4Formula weight 170.07Temperature 140(2) KWavelength 0.71073 ÅCrystal size 0.080 x 0.290 x 0.380 mmCrystal habit clear orange bladeCrystal system monoclinicSpace group P 1 21/c 1Unit cell dimensions a = 10.7152(18) Å α = 90°

b = 8.3768(14) Å β = 97.084(2)°c = 6.7473(11) Å γ = 90°


74

Table S52: Data collection and structure refinement for 5·H2O.


Index ranges -13

Table S53: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for 5·H2O.

U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.x/a y/b z/c U(eq)

C1 0.05565(19) 0.7815(3) 0.3442(3)0.0187(5)

C2 0.24067(19) 0.7865(3) 0.4849(3)0.0187(4)

N1 0.22340(16) 0.6329(2) 0.4604(3)0.0211(4)

N2 0.10265(16) 0.6299(2) 0.3707(3)0.0208(4)

N3 0.14593(16) 0.8854(2) 0.4196(3)0.0199(4)

N4 0.35968(17) 0.8441(2) 0.5835(3)0.0223(4)

Na1 0.80324(8) 0.66720(10)0.04436(12)

0.0233(3)

O1 0.37419(14)0.98885(19) 0.6013(2)

0.0276(4)

O2 0.43905(14)0.74447(19) 0.6465(3)

0.0313(4)

O3 0.94459(13)0.81417(18) 0.2647(2)

0.0219(4)

O4 0.68603(17) 0.8485(2) 0.8340(3)0.0259(4)

Table S54: Bond lengths (Å) for 5·H2O.C1-O3 1.273(2) C1-N3 1.353(3)C1-N2 1.370(3) C2-N1 1.308(3)C2-N3 1.342(3) C2-N4 1.446(3)N1-N2 1.359(2) N2-H1 0.89(3)N3-Na1 2.4282(19) N4-O1 1.226(2)N4-O2 1.229(2) Na1-O4 2.3365(19)Na1-O3 2.3377(16) Na1-N3 2.4282(19)Na1-O4 2.454(2) Na1-O1 2.5203(17)Na1-O3 2.5658(17) Na1-Na1 3.6477(8)Na1-Na1 3.6477(8) Na1-H2 2.60(4)O1-Na1 2.5202(17) O3-Na1 2.5658(17)O4-Na1 2.454(2) O4-H2 0.78(4)O4-H3 0.75(3)

76

Table S55: Bond angles (°) for 5·H2O.

O3-C1-N3 127.43(19) O3-C1-N2 124.33(19)N3-C1-N2 108.23(17) N1-C2-N3 118.44(19)N1-C2-N4 119.30(19) N3-C2-N4 122.25(19)C2-N1-N2 100.76(17) N1-N2-C1 110.83(17)N1-N2-H1 118.8(16) C1-N2-H1 129.5(17)C2-N3-C1 101.74(17) C2-N3-Na1 114.58(14)C1-N3-Na1 143.52(14) O1-N4-O2 124.29(18)O1-N4-C2 117.94(18) O2-N4-C2 117.76(18)O4-Na1-O3 107.55(7) O4-Na1-N3 142.18(7)O3-Na1-N3 109.19(6) O4-Na1-O4 103.25(7)O3-Na1-O4 82.92(6) N3-Na1-O4 89.92(7)O4-Na1-O1 79.95(6) O3-Na1-O1 163.46(7)N3-Na1-O1 67.16(6) O4-Na1-O1 80.98(6)O4-Na1-O3 80.54(6) O3-Na1-O3 92.34(5)N3-Na1-O3 89.27(6) O4-Na1-O3 174.63(6)O1-Na1-O3 103.57(6) O4-Na1-Na1 41.61(5)O3-Na1-Na1 108.30(5) N3-Na1-Na1 115.89(5)O4-Na1-Na1 144.64(5) O1-Na1-Na1 87.18(4)O3-Na1-Na1 39.59(4) O4-Na1-Na1 104.67(6)O3-Na1-Na1 44.39(4) N3-Na1-Na1 107.62(5)O4-Na1-Na1 39.22(4) O1-Na1-Na1 120.00(4)O3-Na1-Na1 136.41(4) Na1-Na1-Na1 135.30(5)O4-Na1-H2 17.0(8) O3-Na1-H2 92.0(8)N3-Na1-H2 158.7(8) O4-Na1-H2 94.8(8)O1-Na1-H2 93.1(8) O3-Na1-H2 87.8(8)Na1-Na1-H2 52.5(8) Na1-Na1-H2 88.7(8)N4-O1-Na1 117.87(13) C1-O3-Na1 130.78(13)C1-O3-Na1 108.02(12) Na1-O3-Na1 96.02(6)Na1-O4-Na1 99.17(7) Na1-O4-H2 101.(3)Na1-O4-H2 120.(3) Na1-O4-H3 122.(2)Na1-O4-H3 110.(2) H2-O4-H3 106.(3)

78

Table S56: Anisotropic atomic displacement parameters (Å2) for 5·H2O.

The anisotropic atomic displacement factor exponent takes the form: -2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]U11 U22 U33 U23 U13 U12

C1 0.0198(10) 0.0235(11) 0.0130(10) -0.0015(8) 0.0023(8) -0.0008(8)C2 0.0181(10) 0.0231(11) 0.0150(10) 0.0000(8) 0.0024(8) -0.0004(8)N1 0.0195(9) 0.0220(9) 0.0215(10) 0.0001(7) 0.0011(7) -0.0005(7)N2 0.0212(9) 0.0183(10) 0.0222(10) -0.0012(7) -0.0007(7) -0.0028(7)N3 0.0221(9) 0.0181(10) 0.0190(9) 0.0002(7) 0.0009(7) 0.0006(7)N4 0.0205(9) 0.0239(11) 0.0220(10) 0.0011(7) 0.0003(7) 0.0000(7)Na1 0.0239(5) 0.0194(5) 0.0250(5) 0.0004(3) -0.0034(3) -0.0008(3)

O1 0.0262(9) 0.0213(9) 0.0333(10) -0.0009(7) -0.0040(7) -0.0049(7)

O2 0.0228(8) 0.0285(9) 0.0401(10) 0.0022(7) -0.0059(7) 0.0044(7)

O3 0.0201(7) 0.0207(8) 0.0236(8) -0.0017(6) -0.0024(6) 0.0004(6)

O4 0.0214(9) 0.0211(9) 0.0333(10) -0.0011(7) -0.0038(7) -0.0003(7)

Table S57: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) 5·H2O.

x/a y/b z/c U(eq)H1 0.071(2) 0.538(3) 0.321(4) 0.034(7)H2 -0.309(3) 0.925(5) -0.100(6) 0.065(12)H3 -0.383(3) 0.837(4) -0.199(5) 0.048(10)

79

Crystal Structure Report for the co-crystal of 5-azido-3-nitro-1,2,4-triazole and PPN+ 5-azido-3-nitro-1,2,4-triazolate 6

Figure S32: Projection of the packing in 6 perpendicular to the 001 plane. Hydrogen atoms have been omitted for clarity.


80



Identification code XGCMK4_02Chemical formula C40H31N15O4P2Formula weight 847.74Temperature 100(2) KWavelength 0.71073 ÅCrystal size 0.220 x 0.264 x 0.438 mmCrystal habit orange blade/prismCrystal system triclinicSpace group P -1Unit cell dimensions a = 11.1121(11) Å α = 70.424(2)°

b = 12.5247(12) Å β = 72.600(2)°c = 16.0476(16) Å γ = 83.653(2)°


81


Diffractometer Bruker APEX DUORadiation source fine-focus tube, MoKα Theta range for data collection 1.40 to 30.67°

Index ranges -15



x/a y/b z/c U(eq)P1 0.09557(5) 0.26692(4) 0.28922(4) 0.01446(12)P2 0.90657(5) 0.23075(4) 0.19377(4) 0.01551(12)N15 0.00948(18) 0.23880(16) 0.23871(13) 0.0253(4)C5 0.0105(2) 0.29560(17) 0.39339(15) 0.0185(4)C6 0.0699(2) 0.2816(2) 0.46145(16) 0.0275(5)C7 0.0090(3) 0.3150(2) 0.53796(17) 0.0334(6)C8 0.8879(3) 0.3594(2) 0.54780(17) 0.0308(6)C9 0.8270(2) 0.37079(19) 0.48216(17) 0.0286(5)C10 0.8883(2) 0.34021(18) 0.40428(16) 0.0227(5)C11 0.3270(2) 0.1594(2) 0.30077(18) 0.0296(5)C12 0.4015(3) 0.0644(2) 0.3275(2) 0.0402(7)C13 0.3472(3) 0.9592(2) 0.37416(19) 0.0352(6)C14 0.2189(3) 0.94728(19) 0.39500(17) 0.0287(5)C15 0.1432(2) 0.04121(18) 0.36871(16) 0.0229(5)C16 0.1979(2) 0.14807(17) 0.32080(14) 0.0180(4)C17 0.2087(2) 0.4725(2) 0.25006(19) 0.0311(6)C18 0.2804(2) 0.5667(2) 0.1917(2) 0.0364(6)C19 0.3347(3) 0.5763(2) 0.1016(2) 0.0425(8)C20 0.3206(4) 0.4917(3) 0.0684(2) 0.0658(12)C21 0.2483(3) 0.3971(3) 0.12609(18) 0.0472(8)C22 0.1922(2) 0.38809(17) 0.21693(15) 0.0178(4)C23 0.8098(2) 0.10924(17) 0.26267(16) 0.0196(4)C24 0.7624(2) 0.04720(18) 0.22188(17) 0.0233(5)C25 0.6989(2) 0.94668(19) 0.27626(19) 0.0297(6)C26 0.6847(2) 0.9086(2) 0.37001(19) 0.0325(6)C27 0.7282(3) 0.9705(2) 0.41079(18) 0.0340(6)C28 0.7918(2) 0.0716(2) 0.35704(17) 0.0269(5)C29 0.0913(2) 0.15366(17) 0.06798(15) 0.0206(4)C30 0.1388(2) 0.12568(18) 0.98725(16) 0.0248(5)C31 0.0718(2) 0.1535(2) 0.92284(17) 0.0282(5)C32 0.9582(2) 0.2122(2) 0.93707(17) 0.0296(5)C33 0.9102(2) 0.2414(2) 0.01690(16) 0.0253(5)C34 0.9762(2) 0.21056(17) 0.08342(15) 0.0188(4)C35 0.8073(2) 0.35489(17) 0.17528(14) 0.0180(4)C36 0.6037(3) 0.4466(2) 0.18575(17) 0.0317(6)C37 0.6621(3) 0.5506(2) 0.13853(17) 0.0329(6)C38 0.6765(2) 0.34869(19) 0.20398(16) 0.0237(5)

83

x/a y/b z/c U(eq)C39 0.7912(3) 0.55774(19) 0.11079(17) 0.0314(6)C40 0.8655(2) 0.46049(18) 0.12879(16) 0.0251(5)O1 0.5121(2) 0.31599(16) 0.49138(15) 0.0480(6)O2 0.3297(2) 0.3695(2) 0.46664(17) 0.0584(7)N1 0.4417(2) 0.38496(19) 0.45384(16) 0.0366(5)N2 0.4245(2) 0.57188(18) 0.35076(14) 0.0294(5)N3 0.5092(2) 0.65644(17) 0.30064(14) 0.0284(5)N4 0.7243(2) 0.68974(17) 0.27086(15) 0.0304(5)N5 0.8260(2) 0.64435(17) 0.28313(14) 0.0301(5)N6 0.9244(2) 0.6157(2) 0.28641(18) 0.0430(6)N7 0.61686(19) 0.51523(16) 0.37500(13) 0.0254(4)C1 0.4949(2) 0.4931(2) 0.39243(16) 0.0261(5)C2 0.6199(2) 0.61936(19) 0.31652(16) 0.0244(5)O3 0.4301(2) 0.20555(16) 0.02864(15) 0.0488(6)O4 0.6196(2) 0.13758(18) 0.02235(17) 0.0573(6)N8 0.5049(2) 0.12851(19) 0.04917(16) 0.0364(5)N9 0.5284(2) 0.93336(18) 0.13478(15) 0.0316(5)N10 0.4449(2) 0.84889(17) 0.18828(14) 0.0288(5)N11 0.2258(2) 0.82136(17) 0.23875(15) 0.0311(5)N12 0.1216(2) 0.87044(17) 0.24167(15) 0.0300(5)N13 0.0211(2) 0.9024(2) 0.25172(18) 0.0423(6)N14 0.3286(2) 0.00026(16) 0.13843(14) 0.0259(4)C3 0.4534(2) 0.0182(2) 0.10812(17) 0.0275(5)C4 0.3300(2) 0.89180(19) 0.18848(16) 0.0249(5)

84

Table S46: Bond lengths (Å) for 6.

P1-N15 1.5575(19) P1-C5 1.789(2)P1-C16 1.797(2) P1-C22 1.799(2)P2-N15 1.5510(19) P2-C23 1.794(2)P2-C35 1.797(2) P2-C34 1.799(2)C5-C6 1.392(3) C5-C10 1.394(3)C6-C7 1.387(3) C6-H6 0.95C7-C8 1.382(4) C7-H7 0.95C8-C9 1.376(4) C8-H8 0.95C9-C10 1.388(3) C9-H9 0.95C10-H10 0.95 C11-C16 1.386(3)C11-C12 1.392(3) C11-H11 0.95C12-C13 1.381(4) C12-H12 0.95C13-C14 1.377(4) C13-H13 0.95C14-C15 1.389(3) C14-H14 0.95C15-C16 1.401(3) C15-H15 0.95C17-C22 1.383(3) C17-C18 1.387(3)C17-H17 0.95 C18-C19 1.359(4)C18-H18 0.95 C19-C20 1.377(5)C19-H19 0.95 C20-C21 1.392(4)C20-H20 0.95 C21-C22 1.374(3)C21-H21 0.95 C23-C28 1.385(3)C23-C24 1.396(3) C24-C25 1.391(3)C24-H24 0.95 C25-C26 1.382(4)C25-H25 0.95 C26-C27 1.368(4)C26-H26 0.95 C27-C28 1.396(3)C27-H27 0.95 C28-H28 0.95C29-C34 1.391(3) C29-C30 1.391(3)C29-H29 0.95 C30-C31 1.381(3)C30-H30 0.95 C31-C32 1.385(3)C31-H31 0.95 C32-C33 1.386(3)C32-H32 0.95 C33-C34 1.399(3)C33-H33 0.95 C35-C38 1.390(3)C35-C40 1.401(3) C36-C37 1.387(4)C36-C38 1.387(3) C36-H36 0.95C37-C39 1.373(4) C37-H37 0.95C38-H38 0.95 C39-C40 1.390(3)C39-H39 0.95 C40-H40 0.95O1-N1 1.226(3) O2-N1 1.226(3)N1-C1 1.445(3) N2-C1 1.316(3)N2-N3 1.361(3) N3-C2 1.332(3)

85

N3-H1 0.9027 N4-N5 1.247(3)N4-C2 1.395(3) N5-N6 1.123(3)N7-C2 1.324(3) N7-C1 1.340(3)O3-N8 1.226(3) O4-N8 1.222(3)N8-C3 1.451(3) N9-C3 1.312(3)N9-N10 1.360(3) N10-C4 1.329(3)N10-H3 0.8854 N11-N12 1.245(3)N11-C4 1.400(3) N12-N13 1.127(3)N14-C4 1.328(3) N14-C3 1.343(3)

86

Table S47: Bond angles (°) for 6.

N15-P1-C5 113.75(11) N15-P1-C16 109.56(10)C5-P1-C16 106.43(10) N15-P1-C22 111.51(10)C5-P1-C22 107.17(10) C16-P1-C22 108.16(10)N15-P2-C23 110.49(10) N15-P2-C35 113.43(10)C23-P2-C35 109.01(10) N15-P2-C34 111.02(11)C23-P2-C34 105.65(10) C35-P2-C34 106.89(10)P2-N15-P1 168.27(15) C6-C5-C10 119.4(2)C6-C5-P1 119.83(17) C10-C5-P1 120.63(17)C7-C6-C5 120.1(2) C7-C6-H6 120.0C5-C6-H6 120.0 C8-C7-C6 120.0(2)C8-C7-H7 120.0 C6-C7-H7 120.0C9-C8-C7 120.5(2) C9-C8-H8 119.8C7-C8-H8 119.8 C8-C9-C10 120.0(2)C8-C9-H9 120.0 C10-C9-H9 120.0C9-C10-C5 120.1(2) C9-C10-H10 119.9C5-C10-H10 119.9 C16-C11-C12 119.8(2)C16-C11-H11 120.1 C12-C11-H11 120.1C13-C12-C11 120.3(2) C13-C12-H12 119.9C11-C12-H12 119.9 C14-C13-C12 120.3(2)C14-C13-H13 119.8 C12-C13-H13 119.8C13-C14-C15 120.1(2) C13-C14-H14 119.9C15-C14-H14 119.9 C14-C15-C16 119.8(2)C14-C15-H15 120.1 C16-C15-H15 120.1C11-C16-C15 119.7(2) C11-C16-P1 122.30(16)C15-C16-P1 118.00(17) C22-C17-C18 120.3(3)C22-C17-H17 119.9 C18-C17-H17 119.9C19-C18-C17 120.0(3) C19-C18-H18 120.0C17-C18-H18 120.0 C18-C19-C20 120.1(2)C18-C19-H19 119.9 C20-C19-H19 119.9C19-C20-C21 120.4(3) C19-C20-H20 119.8C21-C20-H20 119.8 C22-C21-C20 119.5(3)C22-C21-H21 120.3 C20-C21-H21 120.3C21-C22-C17 119.7(2) C21-C22-P1 118.54(18)C17-C22-P1 121.71(18) C28-C23-C24 119.9(2)C28-C23-P2 118.83(17) C24-C23-P2 120.98(17)C25-C24-C23 119.7(2) C25-C24-H24 120.1C23-C24-H24 120.1 C26-C25-C24 119.6(2)C26-C25-H25 120.2 C24-C25-H25 120.2C27-C26-C25 121.0(2) C27-C26-H26 119.5C25-C26-H26 119.5 C26-C27-C28 119.9(2)

87

C26-C27-H27 120.0 C28-C27-H27 120.0C23-C28-C27 119.8(2) C23-C28-H28 120.1C27-C28-H28 120.1 C34-C29-C30 119.7(2)C34-C29-H29 120.1 C30-C29-H29 120.1C31-C30-C29 120.3(2) C31-C30-H30 119.9C29-C30-H30 119.9 C30-C31-C32 120.2(2)C30-C31-H31 119.9 C32-C31-H31 119.9C31-C32-C33 120.1(2) C31-C32-H32 119.9C33-C32-H32 119.9 C32-C33-C34 119.8(2)C32-C33-H33 120.1 C34-C33-H33 120.1C29-C34-C33 119.9(2) C29-C34-P2 119.22(17)C33-C34-P2 120.63(17) C38-C35-C40 119.8(2)C38-C35-P2 122.18(16) C40-C35-P2 118.02(17)C37-C36-C38 119.7(2) C37-C36-H36 120.1C38-C36-H36 120.1 C39-C37-C36 120.6(2)C39-C37-H37 119.7 C36-C37-H37 119.7C35-C38-C36 120.1(2) C35-C38-H38 119.9C36-C38-H38 119.9 C37-C39-C40 120.4(2)C37-C39-H39 119.8 C40-C39-H39 119.8C39-C40-C35 119.4(2) C39-C40-H40 120.3C35-C40-H40 120.3 O2-N1-O1 124.7(2)O2-N1-C1 118.2(2) O1-N1-C1 117.1(2)C1-N2-N3 101.4(2) C2-N3-N2 107.59(19)C2-N3-H1 129.5 N2-N3-H1 122.9N5-N4-C2 114.5(2) N6-N5-N4 171.4(3)C2-N7-C1 98.9(2) N2-C1-N7 118.3(2)N2-C1-N1 120.4(2) N7-C1-N1 121.3(2)N7-C2-N3 113.9(2) N7-C2-N4 127.2(2)N3-C2-N4 119.0(2) O4-N8-O3 124.7(2)O4-N8-C3 117.7(2) O3-N8-C3 117.6(2)C3-N9-N10 101.9(2) C4-N10-N9 107.34(19)C4-N10-H3 127.3 N9-N10-H3 123.2N12-N11-C4 114.7(2) N13-N12-N11 171.5(3)C4-N14-C3 98.7(2) N9-C3-N14 118.1(2)N9-C3-N8 120.4(2) N14-C3-N8 121.5(2)N14-C4-N10 114.0(2) N14-C4-N11 127.1(2)N10-C4-N11 118.8(2)

Table S62: Torsion angles (°) for 6.

C23-P2-N15-P1 -105.3(7) C35-P2-N15-P1 17.4(8)

88

C34-P2-N15-P1 137.8(7) C5-P1-N15-P2 41.3(7)C16-P1-N15-P2 160.3(7) C22-P1-N15-P2 -80.0(7)N15-P1-C5-C6 156.78(18) C16-P1-C5-C6 36.0(2)C22-P1-C5-C6 -79.5(2) N15-P1-C5-C10 -28.2(2)C16-P1-C5-C10 -148.94(17) C22-P1-C5-C10 95.52(19)C10-C5-C6-C7 -1.9(4) P1-C5-C6-C7 173.18(19)C5-C6-C7-C8 1.8(4) C6-C7-C8-C9 0.0(4)C7-C8-C9-C10 -1.6(4) C8-C9-C10-C5 1.4(3)C6-C5-C10-C9 0.3(3) P1-C5-C10-C9 -174.72(17)C16-C11-C12-C13 -0.2(4) C11-C12-C13-C14 -0.3(5)C12-C13-C14-C15 0.4(4) C13-C14-C15-C16 0.1(4)C12-C11-C16-C15 0.7(4) C12-C11-C16-P1 179.5(2)C14-C15-C16-C11 -0.6(3) C14-C15-C16-P1 -179.53(18)N15-P1-C16-C11 129.9(2) C5-P1-C16-C11 -106.7(2)C22-P1-C16-C11 8.2(2) N15-P1-C16-C15 -51.2(2)C5-P1-C16-C15 72.19(19) C22-P1-C16-C15 -172.93(17)C22-C17-C18-C19 0.1(4) C17-C18-C19-C20 -1.2(5)C18-C19-C20-C21 1.6(5) C19-C20-C21-C22 -0.8(6)C20-C21-C22-C17 -0.3(5) C20-C21-C22-P1 178.3(3)C18-C17-C22-C21 0.7(4) C18-C17-C22-P1 -177.8(2)N15-P1-C22-C21 -42.4(2) C5-P1-C22-C21 -167.5(2)C16-P1-C22-C21 78.1(2) N15-P1-C22-C17 136.1(2)C5-P1-C22-C17 11.0(2) C16-P1-C22-C17 -103.3(2)N15-P2-C23-C28 29.9(2) C35-P2-C23-C28 -95.41(19)C34-P2-C23-C28 150.03(18) N15-P2-C23-C24 -144.49(18)C35-P2-C23-C24 90.23(19) C34-P2-C23-C24 -24.3(2)C28-C23-C24-C25 -1.1(3) P2-C23-C24-C25 173.25(17)C23-C24-C25-C26 -0.7(3) C24-C25-C26-C27 2.4(4)C25-C26-C27-C28 -2.3(4) C24-C23-C28-C27 1.2(4)P2-C23-C28-C27 -173.25(19) C26-C27-C28-C23 0.5(4)C34-C29-C30-C31 -0.4(3) C29-C30-C31-C32 1.7(4)C30-C31-C32-C33 -1.3(4) C31-C32-C33-C34 -0.5(4)C30-C29-C34-C33 -1.4(3) C30-C29-C34-P2 172.37(16)C32-C33-C34-C29 1.8(3) C32-C33-C34-P2 -171.83(19)N15-P2-C34-C29 29.8(2) C23-P2-C34-C29 -90.05(18)C35-P2-C34-C29 153.93(17) N15-P2-C34-C33 -156.57(18)C23-P2-C34-C33 83.62(19) C35-P2-C34-C33 -32.4(2)N15-P2-C35-C38 -129.59(19) C23-P2-C35-C38 -6.0(2)C34-P2-C35-C38 107.72(19) N15-P2-C35-C40 51.6(2)C23-P2-C35-C40 175.13(17) C34-P2-C35-C40 -71.11(19)C38-C36-C37-C39 -0.9(4) C40-C35-C38-C36 0.7(3)P2-C35-C38-C36 -178.07(18) C37-C36-C38-C35 0.2(4)

89

C36-C37-C39-C40 0.7(4) C37-C39-C40-C35 0.3(3)C38-C35-C40-C39 -1.0(3) P2-C35-C40-C39 177.91(18)C1-N2-N3-C2 0.7(2) N3-N2-C1-N7 -0.7(3)N3-N2-C1-N1 -179.5(2) C2-N7-C1-N2 0.3(3)C2-N7-C1-N1 179.1(2) O2-N1-C1-N2 -0.8(4)O1-N1-C1-N2 -179.0(2) O2-N1-C1-N7 -179.6(2)O1-N1-C1-N7 2.2(4) C1-N7-C2-N3 0.2(3)C1-N7-C2-N4 -178.6(2) N2-N3-C2-N7 -0.7(3)N2-N3-C2-N4 178.3(2) N5-N4-C2-N7 5.2(4)N5-N4-C2-N3 -173.6(2) C3-N9-N10-C4 -0.4(3)N10-N9-C3-N14 0.5(3) N10-N9-C3-N8 179.2(2)C4-N14-C3-N9 -0.4(3) C4-N14-C3-N8 -179.1(2)O4-N8-C3-N9 3.3(4) O3-N8-C3-N9 -177.9(2)O4-N8-C3-N14 -178.1(2) O3-N8-C3-N14 0.8(4)C3-N14-C4-N10 0.1(3) C3-N14-C4-N11 -179.4(2)N9-N10-C4-N14 0.2(3) N9-N10-C4-N11 179.7(2)N12-N11-C4-N14 -6.3(4) N12-N11-C4-N10 174.2(2)

90

Table S49: Anisotropic atomic displacement parameters (Å2) for 6.The anisotropic atomic displacement factor exponent takes the form: -2π2[ h2 a*2 U11 + ... + 2 h k a* b* U12 ]

U11 U22 U33 U23 U13 U12P1 0.0150(3) 0.0132(2) 0.0150(3) -0.0034(2) -0.0048(2) -0.00087(18)P2 0.0163(3) 0.0129(2) 0.0171(3) -0.0032(2) -0.0057(2) -0.00167(19)N15 0.0231(10) 0.0290(10) 0.0267(10) -0.0079(8) -0.0107(8) -0.0053(8)C5 0.0189(11) 0.0162(9) 0.0175(10) -0.0034(8) -0.0028(8) -0.0010(8)C6 0.0239(12) 0.0371(13) 0.0251(12) -0.0143(10) -0.0080(10) 0.0020(10)C7 0.0370(15) 0.0434(15) 0.0242(12) -0.0166(11) -0.0074(11) -0.0035(12)C8 0.0388(15) 0.0250(12) 0.0233(12) -0.0114(10) 0.0033(11) -0.0015(10)C9 0.0277(13) 0.0212(11) 0.0257(12) -0.0030(9) 0.0020(10) 0.0042(9)C10 0.0233(12) 0.0172(10) 0.0218(11) -0.0013(9) -0.0047(9) 0.0033(8)C11 0.0209(12) 0.0199(11) 0.0402(14) -0.0029(10) -0.0060(11) 0.0033(9)C12 0.0214(13) 0.0318(14) 0.0570(19) -0.0062(13) -0.0081(13) 0.0081(10)C13 0.0397(16) 0.0225(12) 0.0417(15) -0.0089(11) -0.0152(13) 0.0133(11)C14 0.0436(15) 0.0151(10) 0.0278(12) -0.0044(9) -0.0140(11) 0.0022(10)C15 0.0279(12) 0.0167(10) 0.0241(11) -0.0052(9) -0.0083(10) -0.0018(9)C16 0.0213(11) 0.0143(9) 0.0176(10) -0.0051(8) -0.0049(8) 0.0011(8)C17 0.0271(13) 0.0217(11) 0.0415(15) -0.0164(11) 0.0035(11) -0.0051(9)C18 0.0298(14) 0.0174(11) 0.0572(18) -0.0097(12) -0.0067(13) -0.0034(10)C19 0.0426(17) 0.0324(14) 0.0439(16) 0.0178(12) -0.0265(14) -0.0203(12)C20 0.085(3) 0.090(3) 0.0184(13) 0.0025(15) -0.0085(15) -0.064(2)C21 0.064(2) 0.0592(19) 0.0196(12) -0.0089(13) -0.0029(13) -0.0415(16)C22 0.0169(10) 0.0150(9) 0.0204(10) -0.0013(8) -0.0080(8) -0.0012(8)C23 0.0165(11) 0.0141(9) 0.0256(11) -0.0033(8) -0.0063(9) 0.0011(8)C24 0.0207(11) 0.0195(10) 0.0288(12) -0.0090(9) -0.0038(9) -0.0008(8)C25 0.0228(12) 0.0182(11) 0.0485(16) -0.0137(11) -0.0072(11) -0.0003(9)C26 0.0258(13) 0.0163(11) 0.0442(15) 0.0003(10) -0.0044(11) -0.0016(9)C27 0.0353(15) 0.0276(13) 0.0264(13) 0.0046(10) -0.0039(11) -0.0041(10)C28 0.0299(13) 0.0231(11) 0.0252(12) -0.0039(9) -0.0068(10) -0.0044(9)C29 0.0193(11) 0.0153(10) 0.0236(11) -0.0022(8) -0.0051(9) -0.0006(8)C30 0.0229(12) 0.0170(10) 0.0288(12) -0.0064(9) -0.0002(10) 0.0005(8)C31 0.0340(14) 0.0246(12) 0.0243(12) -0.0112(10) -0.0023(10) 0.0014(10)C32 0.0313(14) 0.0357(13) 0.0238(12) -0.0121(10) -0.0090(10) 0.0029(10)C33 0.0231(12) 0.0300(12) 0.0238(11) -0.0110(10) -0.0074(10) 0.0054(9)C34 0.0189(11) 0.0161(9) 0.0206(10) -0.0049(8) -0.0054(9) -0.0002(8)C35 0.0263(12) 0.0145(9) 0.0132(9) -0.0044(8) -0.0059(8) 0.0007(8)C36 0.0349(14) 0.0321(13) 0.0273(13) -0.0125(11) -0.0092(11) 0.0143(11)C37 0.0571(18) 0.0217(12) 0.0230(12) -0.0104(10) -0.0182(12) 0.0176(11)C38 0.0263(12) 0.0215(11) 0.0209(11) -0.0061(9) -0.0056(9) 0.0042(9)C39 0.0575(18) 0.0138(10) 0.0247(12) -0.0053(9) -0.0154(12) 0.0004(10)

91

U11 U22 U33 U23 U13 U12C40 0.0359(14) 0.0163(10) 0.0229(11) -0.0047(9) -0.0086(10) -0.0037(9)O1 0.0458(13) 0.0316(10) 0.0539(13) 0.0120(9) -0.0211(11) -0.0111(9)O2 0.0430(13) 0.0576(14) 0.0667(16) 0.0057(12) -0.0246(12) -0.0243(11)N1 0.0377(14) 0.0351(12) 0.0342(12) 0.0002(10) -0.0147(10) -0.0117(10)N2 0.0298(12) 0.0329(11) 0.0221(10) -0.0070(9) -0.0053(9) 0.0022(9)N3 0.0306(12) 0.0256(10) 0.0240(10) -0.0071(8) -0.0041(9) 0.0067(8)N4 0.0355(13) 0.0187(9) 0.0319(11) -0.0039(8) -0.0067(10) -0.0010(8)N5 0.0384(13) 0.0242(10) 0.0268(11) -0.0052(9) -0.0088(10) -0.0077(9)N6 0.0388(15) 0.0445(14) 0.0437(14) -0.0043(11) -0.0165(12) -0.0090(11)N7 0.0317(11) 0.0208(9) 0.0235(10) -0.0032(8) -0.0109(9) -0.0036(8)C1 0.0309(13) 0.0258(12) 0.0204(11) -0.0047(9) -0.0079(10) -0.0017(10)C2 0.0340(13) 0.0186(10) 0.0196(11) -0.0056(9) -0.0069(10) 0.0007(9)O3 0.0509(13) 0.0257(10) 0.0570(14) 0.0055(9) -0.0172(11) -0.0022(9)O4 0.0386(13) 0.0433(13) 0.0718(16) -0.0042(12) -0.0017(12) -0.0101(10)N8 0.0389(14) 0.0286(12) 0.0359(12) -0.0045(10) -0.0073(11) -0.0047(10)N9 0.0296(12) 0.0299(11) 0.0295(11) -0.0069(9) -0.0045(9) 0.0043(9)N10 0.0306(12) 0.0246(10) 0.0254(10) -0.0043(8) -0.0055(9) 0.0053(8)N11 0.0316(12) 0.0202(10) 0.0365(12) -0.0047(9) -0.0078(10) 0.0016(8)N12 0.0347(13) 0.0216(10) 0.0328(12) -0.0047(9) -0.0122(10) -0.0022(9)N13 0.0331(14) 0.0375(13) 0.0563(16) -0.0087(12) -0.0200(12) 0.0011(10)N14 0.0314(11) 0.0202(9) 0.0254(10) -0.0048(8) -0.0108(9) 0.0020(8)C3 0.0328(14) 0.0227(11) 0.0250(12) -0.0058(10) -0.0073(10) 0.0005(10)C4 0.0333(13) 0.0189(10) 0.0220(11) -0.0063(9) -0.0086(10) 0.0030(9)

92

Table S50: Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å2) for 6.

x/a y/b z/c U(eq)H6 1.1522 0.2492 0.4555 0.033H7 1.0505 0.3074 0.5835 0.04H8 0.8465 0.3822 0.6003 0.037H9 0.7430 0.3996 0.4901 0.034H10 0.8468 0.3497 0.3583 0.027H11 1.3645 0.2318 0.2689 0.036H12 1.4901 0.0720 0.3137 0.048H13 1.3987 -0.1054 0.3919 0.042H14 1.1820 -0.1253 0.4274 0.034H15 1.0547 0.0330 0.3832 0.027H17 1.1708 0.4660 0.3130 0.037H18 1.2916 0.6245 0.2148 0.044H19 1.3824 0.6415 0.0615 0.051H20 1.3605 0.4979 0.0057 0.079H21 1.2378 0.3393 0.1029 0.057H24 0.7733 0.0735 0.1573 0.028H25 0.6654 -0.0956 0.2491 0.036H26 0.6442 -0.1615 0.4067 0.039H27 0.7150 -0.0554 0.4756 0.041H28 0.8227 0.1143 0.3851 0.032H29 1.1374 0.1340 0.1124 0.025H30 1.2177 0.0872 -0.0236 0.03H31 1.1036 0.1324 -0.1314 0.034H32 0.9132 0.2325 -0.1080 0.035H33 0.8326 0.2822 0.0264 0.03H36 0.5143 0.4424 0.2055 0.038H37 0.6123 0.6176 0.1253 0.04H38 0.6368 0.2773 0.2361 0.028H39 0.8301 0.6296 0.0791 0.038H40 0.9548 0.4656 0.1098 0.03H1 0.4888 0.7237 0.2638 0.034H3 0.4651 0.7853 0.2271 0.035

93

Crystal Structure Report for 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate

Figure S35: Disordered anion in the crystal structure of 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.

94

Figure S35: Projection of the packing for 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate perpendicular to the 001 plane. Hydrogens have been omitted for clarity.

Figure S37: Projection of the packing for 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate e perpendicular to the 010 plane. Hydrogens have been omitted for clarity.

95

Figure S38: Projection of the packing 5-azido-3-nitro-1,2,4-triazolate containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate perpendicular to the 100 plane. Hydrogens have been omitted for clarity.

96

Table S58: Sample and crystal data for azide-containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.

Identification code XGC4_MK4_01Chemical formula C38H30N6.51O3.49P2Formula weight 695.60 g/molTemperature 100(2) KWavelength 0.71073 ÅCrystal size 0.265 x 0.290 x 0.630 mmCrystal habit colorless prismCrystal system triclinicSpace group P -1Unit cell dimensions a = 10.8448(6) Å α = 67.1350(10)°

b = 11.9539(7) Å β = 89.7880(10)°c = 14.4364(8) Å γ = 76.1090(10)°


97

Table S- 59: Data collection and structure refinement for azide-containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.

Diffractometer Bruker APEX DUORadiation source fine-focus tube, MoKα Theta range for data collection 1.54 to 31.12°

Index ranges -15

Table S67: Atomic coordinates and equivalent isotropic atomic displacement parameters (Å2) for azide-containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.

U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.x/a y/b z/c U(eq)

C2 0.9428(14) 0.0582(12) 0.7777(11) 0.0148(15)C3 0.0737(3) 0.1239(3) 0.6898(2) 0.0147(5)N2 0.0062(4) 0.1438(4) 0.7618(4) 0.0170(6)N3 0.0547(4) 0.0339(4) 0.6620(4) 0.0189(6)N4 0.9636(13) 0.9893(10) 0.7218(10) 0.0179(11)N5 0.16267(19) 0.19648(17) 0.64199(13) 0.0196(4)N6 0.8522(4) 0.0366(5) 0.8533(3) 0.0170(5)O1 0.22146(14) 0.17132(16) 0.57733(13) 0.0295(4)O2 0.17236(17) 0.27995(15) 0.66839(14) 0.0365(5)O3 0.7804(4) 0.9704(4) 0.8487(3) 0.0228(6)O4 0.8525(4) 0.0813(4) 0.9136(3) 0.0305(6)C1A 0.0838(9) 0.0865(9) 0.6806(7) 0.0157(15)C2A 0.946(4) 0.042(3) 0.770(3) 0.014(5)N1A 0.1858(5) 0.1323(6) 0.6258(5) 0.0295(14)N2A 0.2199(8) 0.2102(6) 0.6494(5) 0.0370(16)N3A 0.2580(8) 0.2824(7) 0.6587(6) 0.056(2)N4A 0.0462(15) 0.0009(10) 0.6599(12) 0.028(2)N5A 0.0305(12) 0.1211(12) 0.7501(11) 0.0195(19)N6A 0.8655(16) 0.0385(18) 0.8441(14) 0.0324(18)O1A 0.8779(11) 0.0961(12) 0.9066(10) 0.0324(18)O2A 0.7793(16) 0.9852(15) 0.8613(12) 0.0324(18)N4B 0.955(4) 0.972(3) 0.720(3) 0.027(5)C010 0.66658(12) 0.19162(13) 0.15608(9) 0.0181(2)C012 0.35097(13) 0.54588(14) 0.45747(12) 0.0236(3)C013 0.98969(12) 0.21868(12) 0.39702(10) 0.0200(2)C015 0.05556(13) 0.64821(13) 0.11279(11) 0.0221(3)C017 0.02578(15) 0.69403(14) 0.93531(11) 0.0274(3)C018 0.71470(13) 0.11730(14) 0.10376(11) 0.0233(3)C019 0.67831(15) 0.54711(14) 0.24273(11) 0.0283(3)C00A 0.55023(11) 0.41887(11) 0.21929(9) 0.0142(2)C01A 0.64215(14) 0.04669(14) 0.08390(11) 0.0244(3)C00B 0.54905(11) 0.18728(10) 0.39071(8) 0.0127(2)C01B 0.99413(15) 0.72524(13) 0.01696(11) 0.0276(3)C00C 0.46868(11) 0.16744(11) 0.46816(9) 0.0139(2)C01C 0.37844(14) 0.65832(14) 0.39866(14) 0.0299(3)C00D 0.47068(12) 0.12611(12) 0.16693(9) 0.0165(2)C01D 0.35777(14) 0.70591(13) 0.29462(14) 0.0291(3)C01E 0.63732(15) 0.63551(14) 0.14510(11) 0.0267(3)

99

x/a y/b z/c U(eq)C00F 0.54421(11) 0.19596(11) 0.18820(9) 0.0139(2)C00G 0.10401(11) 0.37828(11) 0.32664(9) 0.0139(2)C00H 0.27995(11) 0.52879(11) 0.30608(10) 0.0156(2)C00I 0.52043(12) 0.09520(11) 0.56784(9) 0.0166(2)C00J 0.14922(11) 0.53798(11) 0.12649(9) 0.0159(2)C00K 0.30259(11) 0.48065(12) 0.41167(10) 0.0174(2)C00M 0.02967(12) 0.44980(12) 0.37327(10) 0.0183(2)C00N 0.17991(12) 0.50615(12) 0.04443(10) 0.0185(2)C00O 0.50982(12) 0.50845(12) 0.12083(9) 0.0175(2)C00P 0.68011(12) 0.13027(12) 0.41331(9) 0.0173(2)C00Q 0.73076(12) 0.05897(12) 0.51297(10) 0.0192(2)C00R 0.65107(13) 0.04277(11) 0.59021(9) 0.0182(2)C00S 0.93906(12) 0.40333(14) 0.43439(10) 0.0216(3)C00T 0.92011(12) 0.28769(13) 0.44692(10) 0.0209(3)C00U 0.08307(11) 0.26330(11) 0.33754(9) 0.0161(2)C00V 0.52010(14) 0.05131(13) 0.11495(10) 0.0221(3)C00W 0.11793(14) 0.58483(14) 0.94872(10) 0.0239(3)C00X 0.30758(13) 0.64216(12) 0.24739(11) 0.0220(3)C00Y 0.63473(13) 0.43881(12) 0.27994(10) 0.0208(3)C00Z 0.55306(14) 0.61652(13) 0.08404(10) 0.0223(3)N1 0.33265(9) 0.32030(9) 0.24823(8) 0.01404(19)P001 0.48399(3) 0.28456(3) 0.26219(2) 0.01146(7)P002 0.22510(3) 0.43577(3) 0.25100(2) 0.01212(7)

100

Table S61: Bond lengths (Å) for azide-containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.

C2-N2 1.314(14) C2-N4 1.343(18)C2-N6 1.456(14) C3-N2 1.334(4)C3-N3 1.341(4) C3-N5 1.447(4)N3-N4 1.376(15) N5-O1 1.221(2)N5-O2 1.224(3) N6-O4 1.185(6)N6-O3 1.254(5) C1A-N5A 1.310(12)C1A-N4A 1.320(10) C1A-N1A 1.448(11)C1A-C2A 2.00(3) C2A-N4B 1.29(5)C2A-N6A 1.37(4) C2A-N5A 1.42(4)N1A-N2A 1.238(9) N2A-N3A 1.093(10)N4A-N4B 1.33(5) N6A-O2A 1.22(2)N6A-O1A 1.35(2) C010-C018 1.3884(18)C010-C00F 1.4000(16) C012-C01C 1.385(2)C012-C00K 1.3857(18) C013-C00T 1.3885(19)C013-C00U 1.3944(17) C015-C01B 1.3885(19)C015-C00J 1.4012(18) C017-C00W 1.385(2)C017-C01B 1.387(2) C018-C01A 1.386(2)C019-C01E 1.387(2) C019-C00Y 1.3926(19)C00A-C00Y 1.3915(17) C00A-C00O 1.3984(16)C00A-P001 1.8042(12) C01A-C00V 1.391(2)C00B-C00C 1.3971(16) C00B-C00P 1.3988(16)C00B-P001 1.7976(12) C00C-C00I 1.3925(17)C01C-C01D 1.381(2) C00D-C00V 1.3922(18)C00D-C00F 1.3958(17) C01D-C00X 1.396(2)C01E-C00Z 1.387(2) C00F-P001 1.7975(12)C00G-C00M 1.3951(17) C00G-C00U 1.3954(17)C00G-P002 1.7969(12) C00H-C00X 1.3947(18)C00H-C00K 1.4029(18) C00H-P002 1.7975(12)C00I-C00R 1.3871(18) C00J-C00N 1.3948(18)C00J-P002 1.7951(12) C00M-C00S 1.3883(18)C00N-C00W 1.3925(18) C00O-C00Z 1.3880(18)C00P-C00Q 1.3879(17) C00Q-C00R 1.3904(18)C00S-C00T 1.388(2) N1-P001 1.5861(10)N1-P002 1.5927(10)

101

Table S62: Bond angles (°) for azide-containing PPN+ 3,5-dinitro-1H-1,2,4-triazolate.N2-C2-N4 118.2(12) N2-C2-N6 121.9(10)N4-C2-N6 119.9(11) N2-C3-N3 117.1(4)N2-C3-N5 122.0(3) N3-C3-N5 120.9(3)C2-N2-C3 97.9(7) C3-N3-N4 103.7(6)C2-N4-N3 103.0(8) O1-N5-O2 124.7(2)O1-N5-C3 117.7(2) O2-N5-C3 117.6(2)O4-N6-O3 125.7(4) O4-N6-C2 118.3(7)O3-N6-C2 116.0(8) N5A-C1A-N4A 118.8(12)N5A-C1A-N1A 124.7(9) N4A-C1A-N1A 116.4(10)N5A-C1A-C2A 45.1(13) N4A-C1A-C2A 73.8(13)N1A-C1A-C2A 169.8(13) N4B-C2A-N6A 124.(3)N4B-C2A-N5A 117.(3) N6A-C2A-N5A 119.(3)N4B-C2A-C1A 76.(2) N6A-C2A-C1A 160.(3)N5A-C2A-C1A 40.7(10) N2A-N1A-C1A 114.1(8)N3A-N2A-N1A 170.4(9) C1A-N4A-N4B 105.5(18)C1A-N5A-C2A 94.2(16) O2A-N6A-O1A 114.1(15)O2A-N6A-C2A 125.(2) O1A-N6A-C2A 121.(2)C2A-N4B-N4A 104.(2) C018-C010-C00F 119.94(12)C01C-C012-C00K 119.84(14) C00T-C013-C00U 119.71(12)C01B-C015-C00J 119.39(13) C00W-C017-C01B 120.34(13)C01A-C018-C010 120.12(12) C01E-C019-C00Y 120.01(13)C00Y-C00A-C00O 119.36(11) C00Y-C00A-P001 123.40(9)C00O-C00A-P001 117.20(9) C018-C01A-C00V 120.22(12)C00C-C00B-C00P 119.83(11) C00C-C00B-P001 120.09(9)C00P-C00B-P001 120.07(9) C017-C01B-C015 120.38(14)C00I-C00C-C00B 119.68(11) C01D-C01C-C012 120.40(13)C00V-C00D-C00F 119.78(12) C01C-C01D-C00X 120.46(14)C019-C01E-C00Z 120.27(13) C00D-C00F-C010 119.83(11)C00D-C00F-P001 119.59(9) C010-C00F-P001 120.51(9)C00M-C00G-C00U 120.05(11) C00M-C00G-P002 119.81(9)C00U-C00G-P002 120.13(9) C00X-C00H-C00K 119.59(12)C00X-C00H-P002 122.22(10) C00K-C00H-P002 118.07(9)C00R-C00I-C00C 120.23(11) C00N-C00J-C015 120.10(12)C00N-C00J-P002 120.43(10) C015-C00J-P002 119.44(10)C012-C00K-C00H 120.24(13) C00S-C00M-C00G 119.71(12)C00W-C00N-C00J 119.77(13) C00Z-C00O-C00A 120.37(12)C00Q-C00P-C00B 119.96(11) C00P-C00Q-C00R 120.04(12)C00I-C00R-C00Q 120.19(11) C00M-C00S-C00T 120.17(12)C00S-C00T-C013 120.39(12) C013-C00U-C00G 119.87(12)C01A-C00V-C00D 120.09(13) C017-C00W-C00N 120.01(13)

102

C00H-C00X-C01D 119.46(14) C00A-C00Y-C019 120.16(12)C01E-C00Z-C00O 119.83(12) P001-N1-P002 133.27(7)N1-P001-C00F 108.68(5) N1-P001-C00B 112.93(5)C00F-P001-C00B 106.74(5) N1-P001-C00A 113.75(5)C00F-P001-C00A 106.42(5) C00B-P001-C00A 107.91(5)N1-P002-C00J 110.95(6) N1-P002-C00G 109.48(5)C00J-P002-C00G 107.45(6) N1-P002-C00H 114.76(5)C00J-P002-C00H 108.26(

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