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The asymmetric unit of the title compound, C10H10ClN3, contains four independent mol­ecules, two of which are related by a pseudo-inversion centre. Intermolecular N—H...N and N—H...Cl interactions are present in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000284/dn6007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000284/dn6007Isup2.hkl
Contains datablock I

CCDC reference: 180781

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.133
  • Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(13C) - H(9C) ? PLAT_420 Alert C D-H Without Acceptor N(13D) - H(9D) ? PLAT_420 Alert C D-H Without Acceptor N(13A) - H(10A) ? PLAT_420 Alert C D-H Without Acceptor N(13B) - H(10B) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: WinGX98 (Farrugia, 1998) and XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1998) and ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

2-Amino-5-(4-chlorophenyl)-1-methylimidazole top
Crystal data top
C10H10ClN3Z = 8
Mr = 207.66F(000) = 864
Triclinic, P1Dx = 1.401 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.552 (5) ÅCell parameters from 25 reflections
b = 12.833 (5) Åθ = 16.0–17.0°
c = 15.432 (11) ŵ = 0.35 mm1
α = 95.53 (2)°T = 293 K
β = 106.57 (2)°Prism, colourless
γ = 97.02 (2)°0.3 × 0.3 × 0.3 mm
V = 1969.0 (18) Å3
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 1.4°
Graphite monochromatorh = 1312
ω scansk = 1616
8918 measured reflectionsl = 019
8591 independent reflections2 standard reflections every 200 reflections
5153 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.051 w 145 = 1/[σ2(Fo2) + (0.0575P)2 + 0.5308P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133(Δ/σ)max = 0.047
S = 1.01Δρmax = 0.27 e Å3
8591 reflectionsΔρmin = 0.41 e Å3
666 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A0.55936 (7)0.31031 (6)0.26676 (7)0.0770 (3)
N1A1.20433 (19)0.49506 (15)0.26542 (14)0.0370 (5)
C2A1.2954 (2)0.57473 (19)0.25646 (17)0.0386 (6)
N3A1.2412 (2)0.65972 (16)0.23397 (15)0.0441 (5)
C4A1.1082 (2)0.6315 (2)0.22685 (18)0.0409 (6)
C5A1.0807 (2)0.53130 (19)0.24560 (17)0.0368 (5)
C6A0.9566 (2)0.47466 (18)0.25115 (16)0.0347 (5)
C7A0.8348 (3)0.5044 (2)0.20488 (19)0.0424 (6)
C8A0.7140 (3)0.4570 (2)0.2103 (2)0.0468 (7)
C9A0.7111 (2)0.3747 (2)0.26089 (19)0.0441 (6)
C10A0.8275 (3)0.3425 (2)0.3085 (2)0.0504 (7)
C11A0.9487 (3)0.3930 (2)0.3041 (2)0.0462 (7)
C12A1.2323 (3)0.3870 (2)0.2733 (3)0.0530 (8)
N13A1.4247 (2)0.5631 (2)0.2631 (2)0.0513 (6)
H1A1.049 (3)0.680 (2)0.2111 (17)0.050 (8)*
H2A0.841 (2)0.558 (2)0.1730 (17)0.045 (7)*
H3A0.633 (3)0.480 (2)0.175 (2)0.069 (9)*
H4A0.825 (3)0.285 (2)0.3440 (18)0.056 (8)*
H5A1.028 (3)0.376 (2)0.342 (2)0.063 (9)*
H6A1.302 (3)0.379 (2)0.244 (2)0.078 (10)*
H7A1.256 (3)0.375 (3)0.335 (2)0.092 (13)*
H8A1.155 (3)0.342 (2)0.2431 (18)0.054 (8)*
H9A1.478 (3)0.622 (2)0.2612 (17)0.042 (7)*
H10A1.459 (3)0.533 (2)0.303 (2)0.058 (10)*
Cl1B1.28359 (7)1.12207 (6)0.24618 (6)0.0650 (2)
N1B0.63556 (18)0.93474 (15)0.24048 (14)0.0361 (5)
C2B0.5429 (2)0.8526 (2)0.24325 (17)0.0396 (6)
N3B0.5924 (2)0.76350 (16)0.25368 (15)0.0440 (5)
C4B0.7247 (2)0.7903 (2)0.25839 (18)0.0410 (6)
C5B0.7558 (2)0.89446 (18)0.25041 (16)0.0347 (5)
C6B0.8821 (2)0.95344 (18)0.24894 (16)0.0333 (5)
C7B1.0022 (2)0.9222 (2)0.29663 (18)0.0394 (6)
C8B1.1248 (3)0.9717 (2)0.29509 (19)0.0424 (6)
C9B1.1300 (2)1.05629 (19)0.24681 (18)0.0409 (6)
C10B1.0138 (3)1.0897 (2)0.1983 (2)0.0445 (6)
C11B0.8915 (2)1.0375 (2)0.19894 (18)0.0403 (6)
C12B0.6099 (3)1.0427 (2)0.2347 (2)0.0459 (7)
N13B0.4153 (2)0.8655 (2)0.24197 (19)0.0492 (6)
H1B0.787 (3)0.739 (2)0.2659 (17)0.050 (7)*
H2B0.999 (2)0.8671 (19)0.3297 (16)0.039 (7)*
H3B1.204 (3)0.949 (2)0.3284 (18)0.057 (8)*
H4B1.018 (2)1.146 (2)0.1624 (17)0.046 (7)*
H5B0.814 (3)1.057 (2)0.1616 (18)0.051 (8)*
H6B0.692 (3)1.091 (2)0.2642 (18)0.054 (8)*
H7B0.543 (3)1.058 (2)0.270 (2)0.071 (9)*
H8B0.577 (3)1.051 (3)0.173 (2)0.080 (11)*
H9B0.360 (3)0.805 (2)0.2379 (19)0.059 (9)*
H10B0.381 (3)0.907 (2)0.209 (2)0.060 (10)*
Cl1C0.36805 (6)0.09608 (5)0.48288 (5)0.0554 (2)
N1C0.29081 (19)0.27840 (15)0.51065 (14)0.0364 (5)
C2C0.3857 (2)0.36089 (19)0.51278 (18)0.0413 (6)
N3C0.3458 (2)0.45333 (16)0.52289 (17)0.0490 (6)
C4C0.2174 (3)0.4285 (2)0.5283 (2)0.0463 (7)
C5C0.1796 (2)0.32216 (18)0.52118 (17)0.0366 (6)
C6C0.0498 (2)0.26253 (18)0.51368 (16)0.0343 (5)
C7C0.0352 (2)0.3089 (2)0.55622 (18)0.0400 (6)
C8C0.1626 (3)0.2591 (2)0.54628 (18)0.0419 (6)
C9C0.2075 (2)0.16042 (19)0.49546 (17)0.0372 (6)
C10C0.1261 (2)0.1108 (2)0.45387 (18)0.0389 (6)
C11C0.0007 (2)0.16222 (19)0.46294 (17)0.0374 (6)
C12C0.3174 (3)0.1705 (2)0.5178 (2)0.0437 (6)
N13C0.5097 (2)0.3478 (2)0.5070 (2)0.0559 (7)
H1C0.164 (3)0.485 (2)0.5362 (18)0.054 (8)*
H2C0.000 (3)0.374 (2)0.5951 (19)0.065 (9)*
H3C0.218 (3)0.292 (2)0.5777 (19)0.059 (8)*
H4C0.156 (2)0.0440 (19)0.4184 (16)0.039 (7)*
H5C0.053 (3)0.128 (2)0.4305 (18)0.053 (8)*
H6C0.307 (3)0.137 (2)0.457 (2)0.072 (10)*
H7C0.408 (3)0.174 (2)0.5552 (19)0.059 (8)*
H8C0.260 (3)0.136 (2)0.5445 (19)0.058 (9)*
H9C0.521 (3)0.292 (3)0.483 (2)0.074 (12)*
H10C0.557 (3)0.402 (2)0.4984 (19)0.054 (9)*
Cl1D0.36700 (6)0.59721 (5)0.98807 (6)0.0573 (2)
N1D0.29092 (19)0.77988 (15)1.01479 (14)0.0362 (5)
C2D0.3838 (2)0.86228 (19)1.01311 (17)0.0380 (6)
N3D0.3418 (2)0.95447 (16)1.01906 (15)0.0425 (5)
C4D0.2147 (2)0.93007 (19)1.02591 (18)0.0393 (6)
C5D0.1793 (2)0.82403 (18)1.02337 (16)0.0351 (5)
C6D0.0498 (2)0.76419 (18)1.01751 (16)0.0342 (5)
C7D0.0370 (2)0.8119 (2)1.05673 (18)0.0393 (6)
C8D0.1640 (2)0.7621 (2)1.04731 (18)0.0413 (6)
C9D0.2067 (2)0.66113 (19)0.99986 (17)0.0383 (6)
C10D0.1235 (3)0.6105 (2)0.96111 (19)0.0432 (6)
C11D0.0030 (3)0.6621 (2)0.96967 (18)0.0410 (6)
C12D0.3214 (3)0.6746 (2)1.0308 (2)0.0447 (7)
N13D0.5085 (2)0.8487 (2)1.0092 (2)0.0525 (7)
H1D0.166 (2)0.9845 (19)1.0317 (16)0.036 (6)*
H2D0.003 (2)0.881 (2)1.0926 (17)0.047 (7)*
H3D0.218 (3)0.798 (2)1.0745 (18)0.058 (8)*
H4D0.152 (2)0.540 (2)0.9276 (17)0.050 (7)*
H5D0.054 (3)0.630 (2)0.9397 (17)0.046 (7)*
H6D0.416 (3)0.679 (2)1.069 (2)0.072 (10)*
H7D0.310 (3)0.634 (2)0.976 (2)0.064 (10)*
H8D0.261 (3)0.642 (2)1.059 (2)0.066 (9)*
H9D0.518 (3)0.792 (3)0.985 (2)0.066 (11)*
H10D0.556 (3)0.903 (2)1.0015 (19)0.052 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0469 (4)0.0560 (5)0.1411 (9)0.0076 (4)0.0443 (5)0.0286 (5)
N1A0.0332 (10)0.0328 (11)0.0468 (13)0.0069 (8)0.0133 (9)0.0084 (9)
C2A0.0369 (13)0.0361 (13)0.0448 (15)0.0057 (10)0.0153 (11)0.0068 (11)
N3A0.0417 (12)0.0390 (12)0.0550 (14)0.0052 (10)0.0183 (10)0.0130 (10)
C4A0.0365 (13)0.0383 (14)0.0524 (17)0.0094 (11)0.0162 (12)0.0146 (12)
C5A0.0365 (13)0.0363 (13)0.0390 (14)0.0076 (10)0.0125 (11)0.0063 (11)
C6A0.0384 (13)0.0321 (12)0.0350 (14)0.0062 (10)0.0127 (11)0.0057 (10)
C7A0.0432 (14)0.0386 (14)0.0497 (17)0.0114 (11)0.0152 (12)0.0169 (13)
C8A0.0361 (14)0.0477 (16)0.0584 (18)0.0109 (12)0.0133 (13)0.0127 (13)
C9A0.0365 (14)0.0365 (14)0.0632 (18)0.0042 (11)0.0221 (13)0.0058 (13)
C10A0.0481 (16)0.0435 (15)0.068 (2)0.0085 (12)0.0241 (14)0.0246 (14)
C11A0.0391 (14)0.0469 (16)0.0560 (18)0.0103 (12)0.0136 (13)0.0219 (13)
C12A0.0471 (17)0.0376 (16)0.079 (3)0.0127 (13)0.0212 (17)0.0173 (16)
N13A0.0383 (13)0.0478 (15)0.0716 (19)0.0081 (12)0.0193 (13)0.0170 (14)
Cl1B0.0395 (4)0.0490 (4)0.1100 (7)0.0010 (3)0.0300 (4)0.0124 (4)
N1B0.0303 (10)0.0331 (11)0.0450 (12)0.0061 (8)0.0109 (9)0.0062 (9)
C2B0.0354 (13)0.0406 (14)0.0411 (15)0.0016 (11)0.0108 (11)0.0057 (11)
N3B0.0383 (12)0.0387 (12)0.0571 (15)0.0056 (9)0.0162 (10)0.0120 (11)
C4B0.0351 (13)0.0383 (14)0.0528 (17)0.0099 (11)0.0159 (12)0.0083 (12)
C5B0.0331 (12)0.0346 (13)0.0366 (14)0.0071 (10)0.0102 (10)0.0044 (11)
C6B0.0333 (12)0.0333 (13)0.0336 (13)0.0059 (10)0.0106 (10)0.0028 (10)
C7B0.0388 (14)0.0353 (14)0.0449 (16)0.0084 (11)0.0117 (12)0.0095 (12)
C8B0.0340 (13)0.0431 (15)0.0495 (17)0.0101 (11)0.0093 (12)0.0085 (12)
C9B0.0335 (13)0.0346 (13)0.0551 (17)0.0024 (10)0.0172 (12)0.0001 (12)
C10B0.0410 (14)0.0371 (14)0.0576 (18)0.0063 (11)0.0157 (13)0.0149 (13)
C11B0.0333 (13)0.0417 (14)0.0464 (16)0.0085 (11)0.0095 (12)0.0128 (12)
C12B0.0386 (15)0.0338 (14)0.064 (2)0.0086 (12)0.0113 (14)0.0077 (13)
N13B0.0318 (12)0.0467 (14)0.0707 (18)0.0078 (11)0.0151 (11)0.0148 (13)
Cl1C0.0364 (3)0.0502 (4)0.0836 (6)0.0045 (3)0.0242 (3)0.0128 (4)
N1C0.0352 (11)0.0300 (10)0.0469 (13)0.0075 (8)0.0154 (9)0.0067 (9)
C2C0.0371 (13)0.0338 (14)0.0519 (17)0.0044 (11)0.0121 (12)0.0061 (12)
N3C0.0414 (12)0.0301 (11)0.0775 (17)0.0048 (9)0.0222 (11)0.0057 (11)
C4C0.0373 (14)0.0339 (14)0.068 (2)0.0076 (11)0.0178 (13)0.0020 (13)
C5C0.0330 (12)0.0328 (13)0.0439 (15)0.0071 (10)0.0113 (11)0.0026 (11)
C6C0.0342 (12)0.0317 (12)0.0383 (14)0.0075 (10)0.0114 (11)0.0070 (10)
C7C0.0407 (14)0.0364 (14)0.0439 (16)0.0101 (11)0.0142 (12)0.0000 (12)
C8C0.0389 (14)0.0447 (15)0.0468 (16)0.0148 (12)0.0177 (12)0.0045 (12)
C9C0.0316 (12)0.0380 (13)0.0454 (15)0.0087 (10)0.0136 (11)0.0124 (11)
C10C0.0386 (14)0.0328 (13)0.0439 (16)0.0045 (11)0.0116 (11)0.0017 (12)
C11C0.0391 (13)0.0344 (13)0.0411 (15)0.0081 (11)0.0162 (11)0.0008 (11)
C12C0.0443 (16)0.0336 (14)0.059 (2)0.0120 (12)0.0204 (15)0.0125 (13)
N13C0.0410 (13)0.0396 (15)0.097 (2)0.0083 (12)0.0336 (14)0.0136 (15)
Cl1D0.0330 (3)0.0497 (4)0.0879 (6)0.0009 (3)0.0179 (3)0.0107 (4)
N1D0.0346 (11)0.0311 (10)0.0465 (13)0.0052 (8)0.0171 (9)0.0079 (9)
C2D0.0350 (13)0.0341 (13)0.0473 (16)0.0052 (10)0.0150 (11)0.0093 (11)
N3D0.0353 (11)0.0344 (11)0.0596 (14)0.0042 (9)0.0157 (10)0.0120 (10)
C4D0.0355 (13)0.0302 (13)0.0552 (17)0.0078 (10)0.0154 (12)0.0111 (12)
C5D0.0345 (12)0.0340 (13)0.0378 (14)0.0072 (10)0.0114 (10)0.0059 (11)
C6D0.0331 (12)0.0338 (13)0.0363 (14)0.0044 (10)0.0106 (10)0.0088 (10)
C7D0.0390 (13)0.0332 (13)0.0462 (16)0.0059 (11)0.0154 (12)0.0001 (12)
C8D0.0352 (13)0.0417 (15)0.0492 (16)0.0099 (11)0.0159 (12)0.0028 (12)
C9D0.0307 (12)0.0395 (14)0.0450 (15)0.0049 (10)0.0107 (11)0.0101 (12)
C10D0.0408 (14)0.0352 (14)0.0504 (17)0.0007 (11)0.0142 (12)0.0018 (12)
C11D0.0392 (14)0.0397 (14)0.0469 (16)0.0044 (11)0.0202 (12)0.0002 (12)
C12D0.0476 (17)0.0300 (14)0.063 (2)0.0102 (12)0.0239 (15)0.0103 (13)
N13D0.0417 (13)0.0361 (14)0.087 (2)0.0077 (11)0.0301 (13)0.0114 (14)
Geometric parameters (Å, º) top
Cl1A—C9A1.740 (3)Cl1C—C9C1.740 (2)
N1A—C2A1.360 (3)N1C—C2C1.356 (3)
N1A—C5A1.400 (3)N1C—C5C1.404 (3)
N1A—C12A1.461 (3)N1C—C12C1.455 (3)
C2A—N3A1.323 (3)C2C—N3C1.316 (3)
C2A—N13A1.367 (3)C2C—N13C1.366 (3)
N3A—C4A1.375 (3)N3C—C4C1.382 (3)
C4A—C5A1.360 (3)C4C—C5C1.358 (3)
C4A—H1A0.93 (3)C4C—H1C0.99 (3)
C5A—C6A1.447 (3)C5C—C6C1.454 (3)
C6A—C11A1.398 (3)C6C—C11C1.396 (3)
C6A—C7A1.398 (3)C6C—C7C1.407 (3)
C7A—C8A1.373 (4)C7C—C8C1.375 (4)
C7A—H2A0.89 (3)C7C—H2C0.95 (3)
C8A—C9A1.374 (4)C8C—C9C1.375 (4)
C8A—H3A0.97 (3)C8C—H3C0.98 (3)
C9A—C10A1.374 (4)C9C—C10C1.388 (3)
C10A—C11A1.384 (4)C10C—C11C1.380 (3)
C10A—H4A0.96 (3)C10C—H4C0.94 (2)
C11A—H5A0.94 (3)C11C—H5C0.96 (3)
C12A—H6A0.98 (3)C12C—H6C0.96 (3)
C12A—H7A0.95 (4)C12C—H7C0.96 (3)
C12A—H8A0.91 (3)C12C—H8C0.92 (3)
N13A—H9A0.89 (3)N13C—H9C0.81 (3)
N13A—H10A0.78 (3)N13C—H10C0.85 (3)
Cl1B—C9B1.737 (3)Cl1D—C9D1.738 (2)
N1B—C2B1.360 (3)N1D—C2D1.359 (3)
N1B—C5B1.402 (3)N1D—C5D1.402 (3)
N1B—C12B1.450 (3)N1D—C12D1.454 (3)
C2B—N3B1.319 (3)C2D—N3D1.317 (3)
C2B—N13B1.371 (3)C2D—N13D1.365 (3)
N3B—C4B1.376 (3)N3D—C4D1.376 (3)
C4B—C5B1.363 (3)C4D—C5D1.360 (3)
C4B—H1B0.97 (3)C4D—H1D0.93 (2)
C5B—C6B1.457 (3)C5D—C6D1.457 (3)
C6B—C11B1.395 (3)C6D—C11D1.397 (3)
C6B—C7B1.399 (3)C6D—C7D1.401 (3)
C7B—C8B1.378 (4)C7D—C8D1.373 (3)
C7B—H2B0.91 (2)C7D—H2D0.96 (3)
C8B—C9B1.379 (4)C8D—C9D1.380 (4)
C8B—H3B0.95 (3)C8D—H3D0.93 (3)
C9B—C10B1.384 (4)C9D—C10D1.384 (3)
C10B—C11B1.383 (4)C10D—C11D1.380 (4)
C10B—H4B0.96 (3)C10D—H4D0.96 (3)
C11B—H5B0.94 (3)C11D—H5D0.92 (3)
C12B—H6B0.96 (3)C12D—H6D0.99 (3)
C12B—H7B1.04 (3)C12D—H7D0.92 (3)
C12B—H8B0.93 (3)C12D—H8D0.95 (3)
N13B—H9B0.89 (3)N13D—H9D0.82 (3)
N13B—H10B0.82 (3)N13D—H10D0.85 (3)
C2A—N1A—C5A107.06 (19)C2C—N1C—C5C106.64 (19)
C2A—N1A—C12A122.8 (2)C2C—N1C—C12C123.5 (2)
C5A—N1A—C12A128.7 (2)C5C—N1C—C12C128.4 (2)
N3A—C2A—N1A112.2 (2)N3C—C2C—N1C112.7 (2)
N3A—C2A—N13A125.0 (2)N3C—C2C—N13C124.5 (2)
N1A—C2A—N13A122.7 (2)N1C—C2C—N13C122.8 (2)
C2A—N3A—C4A104.3 (2)C2C—N3C—C4C104.3 (2)
C5A—C4A—N3A112.4 (2)C5C—C4C—N3C111.9 (2)
C5A—C4A—H1A127.8 (16)C5C—C4C—H1C127.1 (16)
N3A—C4A—H1A119.9 (16)N3C—C4C—H1C121.0 (16)
C4A—C5A—N1A104.1 (2)C4C—C5C—N1C104.4 (2)
C4A—C5A—C6A129.6 (2)C4C—C5C—C6C129.6 (2)
N1A—C5A—C6A126.2 (2)N1C—C5C—C6C125.5 (2)
C11A—C6A—C7A116.0 (2)C11C—C6C—C7C117.1 (2)
C11A—C6A—C5A124.2 (2)C11C—C6C—C5C123.7 (2)
C7A—C6A—C5A119.7 (2)C7C—C6C—C5C119.1 (2)
C8A—C7A—C6A122.7 (2)C8C—C7C—C6C121.6 (2)
C8A—C7A—H2A121.6 (16)C8C—C7C—H2C120.6 (17)
C6A—C7A—H2A115.7 (16)C6C—C7C—H2C117.7 (17)
C7A—C8A—C9A119.2 (2)C7C—C8C—C9C119.6 (2)
C7A—C8A—H3A118.7 (18)C7C—C8C—H3C119.7 (16)
C9A—C8A—H3A122.1 (18)C9C—C8C—H3C120.6 (16)
C10A—C9A—C8A120.8 (2)C8C—C9C—C10C120.8 (2)
C10A—C9A—Cl1A118.8 (2)C8C—C9C—Cl1C120.09 (19)
C8A—C9A—Cl1A120.4 (2)C10C—C9C—Cl1C119.14 (19)
C9A—C10A—C11A119.2 (3)C11C—C10C—C9C119.2 (2)
C9A—C10A—H4A120.3 (16)C11C—C10C—H4C119.2 (15)
C11A—C10A—H4A120.4 (16)C9C—C10C—H4C121.5 (15)
C10A—C11A—C6A122.1 (2)C10C—C11C—C6C121.7 (2)
C10A—C11A—H5A118.4 (18)C10C—C11C—H5C117.3 (16)
C6A—C11A—H5A119.3 (18)C6C—C11C—H5C120.9 (16)
N1A—C12A—H6A105.7 (19)N1C—C12C—H6C107.3 (18)
N1A—C12A—H7A111 (2)N1C—C12C—H7C108.3 (17)
H6A—C12A—H7A114 (3)H6C—C12C—H7C110 (2)
N1A—C12A—H8A107.0 (17)N1C—C12C—H8C109.6 (17)
H6A—C12A—H8A112 (3)H6C—C12C—H8C112 (3)
H7A—C12A—H8A108 (3)H7C—C12C—H8C110 (2)
C2A—N13A—H9A115.4 (16)C2C—N13C—H9C120 (2)
C2A—N13A—H10A115 (2)C2C—N13C—H10C116.3 (19)
H9A—N13A—H10A111 (3)H9C—N13C—H10C114 (3)
C2B—N1B—C5B106.56 (19)C2D—N1D—C5D106.24 (19)
C2B—N1B—C12B124.0 (2)C2D—N1D—C12D123.7 (2)
C5B—N1B—C12B129.3 (2)C5D—N1D—C12D127.9 (2)
N3B—C2B—N1B112.7 (2)N3D—C2D—N1D112.8 (2)
N3B—C2B—N13B124.9 (2)N3D—C2D—N13D124.9 (2)
N1B—C2B—N13B122.3 (2)N1D—C2D—N13D122.2 (2)
C2B—N3B—C4B104.3 (2)C2D—N3D—C4D104.4 (2)
C5B—C4B—N3B112.0 (2)C5D—C4D—N3D111.8 (2)
C5B—C4B—H1B125.2 (15)C5D—C4D—H1D129.0 (15)
N3B—C4B—H1B122.7 (15)N3D—C4D—H1D119.2 (15)
C4B—C5B—N1B104.4 (2)C4D—C5D—N1D104.8 (2)
C4B—C5B—C6B129.5 (2)C4D—C5D—C6D129.4 (2)
N1B—C5B—C6B126.0 (2)N1D—C5D—C6D125.4 (2)
C11B—C6B—C7B117.0 (2)C11D—C6D—C7D117.2 (2)
C11B—C6B—C5B123.9 (2)C11D—C6D—C5D123.2 (2)
C7B—C6B—C5B119.1 (2)C7D—C6D—C5D119.5 (2)
C8B—C7B—C6B122.0 (2)C8D—C7D—C6D121.8 (2)
C8B—C7B—H2B119.1 (15)C8D—C7D—H2D120.7 (15)
C6B—C7B—H2B118.9 (15)C6D—C7D—H2D117.4 (15)
C7B—C8B—C9B119.2 (2)C7D—C8D—C9D119.4 (2)
C7B—C8B—H3B119.9 (17)C7D—C8D—H3D118.2 (17)
C9B—C8B—H3B120.9 (17)C9D—C8D—H3D122.3 (17)
C8B—C9B—C10B120.8 (2)C8D—C9D—C10D120.6 (2)
C8B—C9B—Cl1B120.02 (19)C8D—C9D—Cl1D119.71 (19)
C10B—C9B—Cl1B119.2 (2)C10D—C9D—Cl1D119.7 (2)
C11B—C10B—C9B119.2 (2)C11D—C10D—C9D119.4 (2)
C11B—C10B—H4B120.3 (15)C11D—C10D—H4D119.0 (15)
C9B—C10B—H4B120.4 (15)C9D—C10D—H4D121.6 (15)
C10B—C11B—C6B121.8 (2)C10D—C11D—C6D121.5 (2)
C10B—C11B—H5B117.9 (16)C10D—C11D—H5D118.6 (16)
C6B—C11B—H5B120.3 (16)C6D—C11D—H5D119.8 (16)
N1B—C12B—H6B109.4 (16)N1D—C12D—H6D110.2 (17)
N1B—C12B—H7B109.5 (16)N1D—C12D—H7D109.4 (19)
H6B—C12B—H7B107 (2)H6D—C12D—H7D108 (2)
N1B—C12B—H8B109 (2)N1D—C12D—H8D109.1 (17)
H6B—C12B—H8B111 (3)H6D—C12D—H8D112 (2)
H7B—C12B—H8B112 (3)H7D—C12D—H8D108 (3)
C2B—N13B—H9B114.8 (18)C2D—N13D—H9D118 (2)
C2B—N13B—H10B116 (2)C2D—N13D—H10D115.2 (19)
H9B—N13B—H10B114 (3)H9D—N13D—H10D116 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13C—H10C···N3Ci0.85 (3)2.11 (3)2.955 (3)173 (3)
N13D—H10D···N3Dii0.85 (3)2.11 (3)2.949 (3)175 (3)
N13A—H9A···N3Biii0.89 (3)2.09 (3)2.979 (4)176 (2)
N13B—H9B···N3Aiv0.89 (3)2.11 (3)2.998 (3)176 (3)
N13C—H9C···Cl1Ciii0.81 (4)2.90 (4)3.646 (3)154 (3)
N13D—H9D···Cl1Diii0.82 (3)2.91 (4)3.650 (3)152 (3)
N13A—H10A···Cl1Aiii0.78 (3)3.21 (3)3.696 (3)122 (3)
N13B—H10B···Cl1Biv0.82 (3)3.11 (3)3.729 (3)134 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+2; (iii) x+1, y, z; (iv) x1, y, z.
 

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