A novel energetic cocrystal composed of CL-20 and 1-methyl-2,4,5-trinitroimidazole with high energy and low sensitivity

A cocrystal explosive comprising 2,4,6,8,10,12-hexa­nitro-2,4,6,8,10,12-hexa­aza­isowurtzitane (CL-20) and 1-methyl-2,4,5-tri­nitro­imidazole (MTNI) (molar ratio, 1:1) was synthesized. The structure of the cocrystal was characterized by single-crystal X-ray diffraction. Its structure was further determined by powder X-ray diffraction, infrared spectroscopy and differential scanning calorimetry which showed that its morphology was different from the morphology of the mechanical mixture of two raw materials. The decomposition temperature of the cocrystal is lower than that of CL-20 and MTNI. The calculated detonation performance is slightly lower than that of HMX, but the cocrystal has excellent sensitivity performance relative to that of CL-20, even lower than that of RDX. These features make this cocrystal ideal to be used in applications with low-sensitivity requirements.

Computing details

Cell refinement: SAINT V8.40A (Bruker, 2019); data reduction: SAINT V8.40A (Bruker, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(I)

Crystal data

C4H3N5O6·C6H6N12O12	F(000) = 1328
Mr = 655.34	Dx = 1.893 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7438 (5) Å	Cell parameters from 9005 reflections
b = 15.8026 (7) Å	θ = 2.5–26.3°
c = 12.5832 (5) Å	µ = 0.18 mm^−1
β = 100.074 (1)°	T = 140 K
V = 2299.22 (17) Å^3	Block, colourless
Z = 4	0.15 × 0.12 × 0.08 mm

Data collection

D8 VENTURE diffractometer	3864 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.050
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1189 before and 0.0429 after correction. The Ratio of minimum to maximum transmission is 0.9085. The λ/2 correction factor is Not present.	θmax = 26.4°, θmin = 2.5°
Tmin = 0.677, Tmax = 0.745	h = −14→14
20681 measured reflections	k = −19→18
4662 independent reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 2.1083P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4662 reflections	Δρmax = 0.34 e Å^−3
407 parameters	Δρmin = −0.33 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.6295 (2)	0.60523 (13)	0.08839 (15)	0.0591 (6)
O2	0.78238 (18)	0.52548 (13)	0.08954 (14)	0.0513 (5)
O3	0.72130 (16)	0.39004 (10)	0.21162 (13)	0.0380 (4)
O4	0.76565 (14)	0.36663 (10)	0.38383 (13)	0.0331 (4)
O5	0.77404 (14)	0.63873 (10)	0.59232 (11)	0.0299 (3)
O6	0.77715 (14)	0.74864 (9)	0.48788 (12)	0.0315 (4)
N1	0.71388 (18)	0.56657 (12)	0.13124 (14)	0.0305 (4)
N2	0.74659 (15)	0.41366 (11)	0.30545 (14)	0.0246 (4)
N3	0.76384 (13)	0.53409 (10)	0.42559 (12)	0.0193 (3)
N4	0.74263 (14)	0.64197 (10)	0.30731 (13)	0.0198 (3)
N5	0.77097 (14)	0.67267 (11)	0.50419 (13)	0.0223 (4)
C7	0.73900 (17)	0.56841 (13)	0.24998 (15)	0.0210 (4)
C8	0.75271 (16)	0.50386 (12)	0.32469 (15)	0.0196 (4)
C9	0.75843 (16)	0.61595 (12)	0.41216 (15)	0.0189 (4)
C10	0.73172 (19)	0.72906 (13)	0.26261 (17)	0.0268 (5)
H10A	0.664251	0.756765	0.283400	0.040*
H10B	0.722116	0.726546	0.183726	0.040*
H10C	0.801589	0.761401	0.291176	0.040*
O7	0.50426 (13)	0.49744 (11)	0.29591 (13)	0.0352 (4)
O8	0.41503 (15)	0.46923 (14)	0.13194 (14)	0.0498 (5)
O9	0.44476 (14)	0.75715 (11)	0.14259 (14)	0.0366 (4)
O10	0.33384 (16)	0.70108 (11)	0.00340 (12)	0.0403 (4)
O11	0.50199 (13)	0.59296 (10)	0.49590 (12)	0.0292 (3)
O12	0.52374 (12)	0.70279 (10)	0.39707 (13)	0.0312 (4)
O13	0.05878 (18)	0.39397 (11)	0.17412 (13)	0.0469 (5)
O14	−0.00172 (13)	0.44080 (10)	0.31688 (12)	0.0322 (4)
O15	0.00829 (13)	0.61493 (10)	0.44965 (12)	0.0300 (3)
O16	0.04781 (14)	0.74639 (10)	0.41902 (13)	0.0350 (4)
O17	−0.04575 (13)	0.68957 (11)	0.18690 (13)	0.0363 (4)
O18	−0.01040 (14)	0.60998 (11)	0.05418 (12)	0.0355 (4)
N6	0.41810 (16)	0.48873 (12)	0.22584 (15)	0.0307 (4)
N7	0.31234 (14)	0.50008 (11)	0.25809 (13)	0.0213 (4)
N8	0.12129 (14)	0.52032 (10)	0.24344 (12)	0.0195 (3)
N9	0.05539 (15)	0.44459 (12)	0.24550 (14)	0.0269 (4)
N10	0.14759 (13)	0.64406 (10)	0.35545 (13)	0.0191 (3)
N11	0.06055 (14)	0.67046 (12)	0.41119 (13)	0.0231 (4)
N12	0.13563 (14)	0.67183 (11)	0.16226 (13)	0.0235 (4)
N13	0.01762 (15)	0.65533 (12)	0.13232 (14)	0.0268 (4)
N14	0.32587 (14)	0.65071 (11)	0.17054 (13)	0.0234 (4)
N15	0.37018 (16)	0.70866 (12)	0.09941 (15)	0.0298 (4)
N16	0.47017 (14)	0.64188 (11)	0.42236 (13)	0.0230 (4)
N17	0.35786 (14)	0.63002 (10)	0.36282 (13)	0.0196 (3)
C1	0.21552 (18)	0.61166 (14)	0.12558 (16)	0.0251 (4)
H1	0.203963	0.609181	0.045000	0.030*
C2	0.21004 (17)	0.52018 (13)	0.17620 (15)	0.0233 (4)
H2	0.195298	0.475574	0.119078	0.028*
C3	0.30740 (16)	0.54629 (12)	0.35876 (15)	0.0186 (4)
H3	0.341706	0.512124	0.423355	0.022*
C4	0.17279 (15)	0.55552 (12)	0.35056 (14)	0.0174 (4)
H4	0.145169	0.523929	0.410060	0.021*
C5	0.31492 (17)	0.68769 (13)	0.27733 (15)	0.0215 (4)
H5	0.355600	0.743412	0.288531	0.026*
C6	0.18125 (17)	0.69849 (13)	0.27472 (15)	0.0219 (4)
H6	0.161189	0.758808	0.286860	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0821 (16)	0.0542 (13)	0.0337 (10)	0.0059 (11)	−0.0100 (10)	0.0014 (9)
O2	0.0644 (13)	0.0553 (12)	0.0387 (10)	−0.0124 (10)	0.0217 (9)	−0.0119 (9)
O3	0.0543 (11)	0.0269 (9)	0.0312 (8)	0.0000 (8)	0.0026 (7)	−0.0098 (7)
O4	0.0369 (9)	0.0228 (8)	0.0374 (9)	−0.0019 (7)	0.0002 (7)	0.0075 (7)
O5	0.0391 (9)	0.0315 (9)	0.0184 (7)	0.0021 (7)	0.0029 (6)	−0.0014 (6)
O6	0.0401 (9)	0.0201 (8)	0.0328 (8)	−0.0038 (6)	0.0018 (7)	−0.0052 (6)
N1	0.0471 (12)	0.0228 (10)	0.0254 (9)	−0.0027 (9)	0.0167 (9)	−0.0023 (8)
N2	0.0220 (9)	0.0213 (9)	0.0304 (9)	−0.0011 (7)	0.0043 (7)	−0.0015 (7)
N3	0.0165 (8)	0.0215 (9)	0.0194 (8)	−0.0008 (6)	0.0018 (6)	0.0012 (6)
N4	0.0220 (8)	0.0182 (9)	0.0198 (8)	−0.0018 (6)	0.0056 (6)	0.0003 (6)
N5	0.0204 (8)	0.0236 (10)	0.0217 (8)	−0.0007 (7)	0.0002 (7)	−0.0036 (7)
C7	0.0227 (10)	0.0225 (11)	0.0186 (9)	−0.0022 (8)	0.0056 (8)	−0.0012 (8)
C8	0.0172 (9)	0.0193 (10)	0.0224 (9)	−0.0012 (7)	0.0038 (7)	−0.0016 (8)
C9	0.0169 (9)	0.0199 (10)	0.0195 (9)	−0.0007 (7)	0.0024 (7)	−0.0009 (7)
C10	0.0345 (11)	0.0202 (11)	0.0269 (10)	−0.0005 (9)	0.0086 (9)	0.0059 (8)
O7	0.0212 (7)	0.0467 (10)	0.0370 (8)	0.0063 (7)	0.0029 (7)	−0.0044 (7)
O8	0.0388 (10)	0.0782 (14)	0.0350 (9)	0.0030 (9)	0.0134 (8)	−0.0242 (9)
O9	0.0338 (9)	0.0347 (9)	0.0439 (9)	−0.0093 (7)	0.0138 (7)	0.0082 (7)
O10	0.0496 (10)	0.0502 (11)	0.0242 (8)	−0.0059 (8)	0.0150 (7)	0.0088 (7)
O11	0.0269 (7)	0.0281 (8)	0.0290 (7)	0.0038 (6)	−0.0048 (6)	0.0009 (6)
O12	0.0219 (7)	0.0320 (9)	0.0400 (9)	−0.0075 (6)	0.0067 (6)	−0.0010 (7)
O13	0.0686 (13)	0.0387 (10)	0.0340 (9)	−0.0250 (9)	0.0102 (9)	−0.0140 (8)
O14	0.0270 (8)	0.0352 (9)	0.0354 (8)	−0.0094 (7)	0.0082 (7)	0.0051 (7)
O15	0.0249 (7)	0.0358 (9)	0.0324 (8)	0.0009 (7)	0.0136 (6)	0.0052 (7)
O16	0.0415 (9)	0.0252 (9)	0.0408 (9)	0.0131 (7)	0.0141 (7)	0.0015 (7)
O17	0.0231 (8)	0.0484 (11)	0.0367 (9)	0.0087 (7)	0.0033 (7)	0.0033 (7)
O18	0.0330 (8)	0.0471 (10)	0.0230 (7)	−0.0058 (7)	−0.0045 (6)	0.0041 (7)
N6	0.0263 (9)	0.0345 (11)	0.0331 (10)	0.0026 (8)	0.0099 (8)	−0.0061 (8)
N7	0.0203 (8)	0.0220 (9)	0.0218 (8)	0.0021 (7)	0.0045 (6)	−0.0023 (7)
N8	0.0200 (8)	0.0206 (9)	0.0177 (7)	−0.0041 (6)	0.0031 (6)	−0.0004 (6)
N9	0.0272 (9)	0.0271 (10)	0.0243 (9)	−0.0079 (7)	−0.0010 (7)	0.0028 (7)
N10	0.0186 (8)	0.0183 (9)	0.0220 (8)	0.0027 (6)	0.0080 (6)	0.0023 (6)
N11	0.0192 (8)	0.0294 (10)	0.0209 (8)	0.0055 (7)	0.0036 (7)	0.0021 (7)
N12	0.0214 (8)	0.0280 (10)	0.0208 (8)	0.0010 (7)	0.0030 (7)	0.0064 (7)
N13	0.0225 (9)	0.0332 (10)	0.0231 (8)	0.0005 (8)	−0.0008 (7)	0.0097 (8)
N14	0.0238 (8)	0.0260 (10)	0.0221 (8)	−0.0028 (7)	0.0086 (7)	0.0052 (7)
N15	0.0290 (10)	0.0303 (10)	0.0328 (10)	0.0008 (8)	0.0130 (8)	0.0097 (8)
N16	0.0175 (8)	0.0244 (9)	0.0264 (8)	0.0006 (7)	0.0019 (7)	−0.0043 (7)
N17	0.0177 (8)	0.0191 (9)	0.0214 (8)	−0.0017 (6)	0.0011 (6)	0.0006 (6)
C1	0.0257 (10)	0.0306 (12)	0.0197 (9)	−0.0006 (9)	0.0056 (8)	0.0028 (8)
C2	0.0239 (10)	0.0268 (11)	0.0192 (9)	−0.0022 (8)	0.0041 (8)	−0.0022 (8)
C3	0.0184 (9)	0.0185 (10)	0.0188 (9)	0.0000 (7)	0.0031 (7)	0.0006 (7)
C4	0.0169 (9)	0.0188 (10)	0.0161 (8)	0.0005 (7)	0.0017 (7)	0.0015 (7)
C5	0.0212 (10)	0.0206 (10)	0.0227 (9)	−0.0004 (8)	0.0042 (8)	0.0032 (8)
C6	0.0243 (10)	0.0194 (10)	0.0218 (9)	0.0008 (8)	0.0038 (8)	0.0045 (8)

Geometric parameters (Å, º)

O1—N1	1.208 (3)	O18—N13	1.215 (2)
O2—N1	1.221 (3)	N6—N7	1.384 (2)
O3—N2	1.224 (2)	N7—C2	1.474 (3)
O4—N2	1.224 (2)	N7—C3	1.472 (2)
O5—N5	1.227 (2)	N8—N9	1.428 (2)
O6—N5	1.222 (2)	N8—C2	1.453 (3)
N1—C7	1.472 (2)	N8—C4	1.486 (2)
N2—C8	1.445 (3)	N10—N11	1.401 (2)
N3—C8	1.341 (2)	N10—C4	1.434 (3)
N3—C9	1.305 (3)	N10—C6	1.438 (2)
N4—C7	1.365 (3)	N12—N13	1.396 (2)
N4—C9	1.363 (2)	N12—C1	1.466 (3)
N4—C10	1.484 (3)	N12—C6	1.484 (3)
N5—C9	1.451 (2)	N14—N15	1.440 (2)
C7—C8	1.377 (3)	N14—C1	1.457 (3)
C10—H10A	0.9800	N14—C5	1.491 (2)
C10—H10B	0.9800	N16—N17	1.411 (2)
C10—H10C	0.9800	N17—C3	1.447 (2)
O7—N6	1.228 (2)	N17—C5	1.433 (2)
O8—N6	1.215 (2)	C1—H1	1.0000
O9—N15	1.218 (2)	C1—C2	1.585 (3)
O10—N15	1.215 (2)	C2—H2	1.0000
O11—N16	1.213 (2)	C3—H3	1.0000
O12—N16	1.222 (2)	C3—C4	1.573 (3)
O13—N9	1.209 (2)	C4—H4	1.0000
O14—N9	1.213 (2)	C5—H5	1.0000
O15—N11	1.218 (2)	C5—C6	1.574 (3)
O16—N11	1.215 (2)	C6—H6	1.0000
O17—N13	1.224 (2)
O1—N1—O2	128.9 (2)	O18—N13—O17	127.59 (18)
O1—N1—C7	116.51 (18)	O18—N13—N12	116.38 (18)
O2—N1—C7	114.61 (19)	N15—N14—C1	114.93 (15)
O3—N2—C8	117.30 (17)	N15—N14—C5	114.11 (16)
O4—N2—O3	124.84 (18)	C1—N14—C5	107.74 (15)
O4—N2—C8	117.85 (17)	O9—N15—N14	115.64 (17)
C9—N3—C8	103.65 (16)	O10—N15—O9	127.30 (19)
C7—N4—C10	126.65 (16)	O10—N15—N14	116.95 (18)
C9—N4—C7	103.95 (16)	O11—N16—O12	126.61 (17)
C9—N4—C10	129.40 (17)	O11—N16—N17	117.05 (16)
O5—N5—C9	115.73 (16)	O12—N16—N17	116.26 (16)
O6—N5—O5	126.02 (17)	N16—N17—C3	118.64 (15)
O6—N5—C9	118.25 (16)	N16—N17—C5	119.20 (16)
N4—C7—N1	122.38 (17)	C5—N17—C3	117.84 (15)
N4—C7—C8	106.31 (16)	N12—C1—H1	111.3
C8—C7—N1	131.08 (18)	N12—C1—C2	113.06 (16)
N3—C8—N2	120.23 (17)	N14—C1—N12	100.24 (16)
N3—C8—C7	111.27 (17)	N14—C1—H1	111.3
C7—C8—N2	128.28 (17)	N14—C1—C2	109.02 (16)
N3—C9—N4	114.82 (17)	C2—C1—H1	111.3
N3—C9—N5	120.87 (16)	N7—C2—C1	113.07 (16)
N4—C9—N5	124.30 (17)	N7—C2—H2	111.6
N4—C10—H10A	109.5	N8—C2—N7	99.97 (14)
N4—C10—H10B	109.5	N8—C2—C1	108.44 (16)
N4—C10—H10C	109.5	N8—C2—H2	111.6
H10A—C10—H10B	109.5	C1—C2—H2	111.6
H10A—C10—H10C	109.5	N7—C3—H3	111.1
H10B—C10—H10C	109.5	N7—C3—C4	100.37 (14)
O7—N6—N7	116.35 (17)	N17—C3—N7	113.99 (15)
O8—N6—O7	127.37 (19)	N17—C3—H3	111.1
O8—N6—N7	116.25 (18)	N17—C3—C4	108.56 (15)
N6—N7—C2	119.10 (15)	C4—C3—H3	111.1
N6—N7—C3	119.28 (15)	N8—C4—C3	105.65 (14)
C3—N7—C2	110.16 (15)	N8—C4—H4	111.0
N9—N8—C2	117.11 (16)	N10—C4—N8	110.49 (15)
N9—N8—C4	115.68 (14)	N10—C4—C3	107.47 (15)
C2—N8—C4	108.02 (14)	N10—C4—H4	111.0
O13—N9—O14	127.74 (19)	C3—C4—H4	111.0
O13—N9—N8	116.92 (17)	N14—C5—H5	111.0
O14—N9—N8	115.25 (17)	N14—C5—C6	105.46 (15)
N11—N10—C4	119.10 (15)	N17—C5—N14	110.66 (16)
N11—N10—C6	119.37 (15)	N17—C5—H5	111.0
C4—N10—C6	117.97 (15)	N17—C5—C6	107.67 (15)
O15—N11—N10	116.55 (17)	C6—C5—H5	111.0
O16—N11—O15	126.94 (17)	N10—C6—N12	113.94 (16)
O16—N11—N10	116.46 (17)	N10—C6—C5	108.47 (15)
N13—N12—C1	116.99 (17)	N10—C6—H6	111.2
N13—N12—C6	119.10 (16)	N12—C6—C5	100.46 (15)
C1—N12—C6	109.89 (15)	N12—C6—H6	111.2
O17—N13—N12	116.02 (17)	C5—C6—H6	111.2
O1—N1—C7—N4	−49.9 (3)	N14—C1—C2—N7	3.1 (2)
O1—N1—C7—C8	123.7 (3)	N14—C1—C2—N8	112.98 (17)
O2—N1—C7—N4	130.1 (2)	N14—C5—C6—N10	115.63 (16)
O2—N1—C7—C8	−56.2 (3)	N14—C5—C6—N12	−4.16 (19)
O3—N2—C8—N3	170.62 (18)	N15—N14—C1—N12	−91.87 (18)
O3—N2—C8—C7	−3.4 (3)	N15—N14—C1—C2	149.23 (16)
O4—N2—C8—N3	−8.5 (3)	N15—N14—C5—N17	−135.50 (16)
O4—N2—C8—C7	177.40 (19)	N15—N14—C5—C6	108.34 (17)
O5—N5—C9—N3	−7.6 (3)	N16—N17—C3—N7	−101.08 (19)
O5—N5—C9—N4	173.65 (17)	N16—N17—C3—C4	147.99 (15)
O6—N5—C9—N3	172.60 (18)	N16—N17—C5—N14	99.76 (19)
O6—N5—C9—N4	−6.2 (3)	N16—N17—C5—C6	−145.46 (16)
N1—C7—C8—N2	0.5 (4)	N17—C3—C4—N8	115.14 (16)
N1—C7—C8—N3	−174.00 (19)	N17—C3—C4—N10	−2.85 (19)
N4—C7—C8—N2	174.93 (18)	N17—C5—C6—N10	−2.6 (2)
N4—C7—C8—N3	0.4 (2)	N17—C5—C6—N12	−122.35 (16)
C7—N4—C9—N3	−0.6 (2)	C1—N12—N13—O17	159.51 (17)
C7—N4—C9—N5	178.21 (17)	C1—N12—N13—O18	−21.7 (2)
C8—N3—C9—N4	0.9 (2)	C1—N12—C6—N10	−87.8 (2)
C8—N3—C9—N5	−178.00 (16)	C1—N12—C6—C5	27.98 (19)
C9—N3—C8—N2	−175.77 (17)	C1—N14—N15—O9	162.24 (18)
C9—N3—C8—C7	−0.8 (2)	C1—N14—N15—O10	−21.4 (3)
C9—N4—C7—N1	175.12 (17)	C1—N14—C5—N17	95.60 (18)
C9—N4—C7—C8	0.1 (2)	C1—N14—C5—C6	−20.6 (2)
C10—N4—C7—N1	−5.0 (3)	C2—N7—C3—N17	−87.74 (19)
C10—N4—C7—C8	180.00 (18)	C2—N7—C3—C4	28.08 (19)
C10—N4—C9—N3	179.47 (18)	C2—N8—N9—O13	−16.7 (3)
C10—N4—C9—N5	−1.7 (3)	C2—N8—N9—O14	166.50 (17)
O7—N6—N7—C2	158.86 (19)	C2—N8—C4—N10	95.97 (18)
O7—N6—N7—C3	19.0 (3)	C2—N8—C4—C3	−19.98 (19)
O8—N6—N7—C2	−22.9 (3)	C3—N7—C2—N8	−40.62 (19)
O8—N6—N7—C3	−162.73 (19)	C3—N7—C2—C1	74.47 (19)
O11—N16—N17—C3	−25.7 (2)	C3—N17—C5—N14	−56.6 (2)
O11—N16—N17—C5	178.09 (17)	C3—N17—C5—C6	58.2 (2)
O12—N16—N17—C3	157.12 (17)	C4—N8—N9—O13	−145.83 (19)
O12—N16—N17—C5	1.0 (2)	C4—N8—N9—O14	37.3 (2)
N6—N7—C2—N8	176.20 (16)	C4—N8—C2—N7	35.78 (19)
N6—N7—C2—C1	−68.7 (2)	C4—N8—C2—C1	−82.78 (18)
N6—N7—C3—N17	55.4 (2)	C4—N10—N11—O15	−2.4 (2)
N6—N7—C3—C4	171.18 (16)	C4—N10—N11—O16	175.28 (16)
N7—C3—C4—N8	−4.68 (18)	C4—N10—C6—N12	54.8 (2)
N7—C3—C4—N10	−122.68 (15)	C4—N10—C6—C5	−56.2 (2)
N9—N8—C2—N7	−96.93 (17)	C5—N14—N15—O9	37.1 (2)
N9—N8—C2—C1	144.50 (16)	C5—N14—N15—O10	−146.56 (19)
N9—N8—C4—N10	−130.55 (16)	C5—N14—C1—N12	36.57 (18)
N9—N8—C4—C3	113.50 (17)	C5—N14—C1—C2	−82.34 (19)
N11—N10—C4—N8	102.61 (18)	C5—N17—C3—N7	55.4 (2)
N11—N10—C4—C3	−142.58 (15)	C5—N17—C3—C4	−55.5 (2)
N11—N10—C6—N12	−103.78 (19)	C6—N10—N11—O15	155.92 (17)
N11—N10—C6—C5	145.26 (16)	C6—N10—N11—O16	−26.4 (2)
N12—C1—C2—N7	−107.49 (18)	C6—N10—C4—N8	−56.0 (2)
N12—C1—C2—N8	2.4 (2)	C6—N10—C4—C3	58.8 (2)
N13—N12—C1—N14	179.19 (15)	C6—N12—N13—O17	23.4 (3)
N13—N12—C1—C2	−64.9 (2)	C6—N12—N13—O18	−157.83 (17)
N13—N12—C6—N10	51.1 (2)	C6—N12—C1—N14	−40.93 (19)
N13—N12—C6—C5	166.90 (16)	C6—N12—C1—C2	75.0 (2)