2-Amino-5-(4-chloro­phenyl)-1-methyl­imidazole

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.

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


 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

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

Crystal data

C10H10ClN3	Z = 8
Mr = 207.66	F(000) = 864
Triclinic, P1	Dx = 1.401 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.552 (5) Å	Cell parameters from 25 reflections
b = 12.833 (5) Å	θ = 16.0–17.0°
c = 15.432 (11) Å	µ = 0.35 mm^−1
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) Å^3

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 1.4°
Graphite monochromator	h = −13→12
ω scans	k = −16→16
8918 measured reflections	l = 0→19
8591 independent reflections	2 standard reflections every 200 reflections
5153 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.051	w 145 = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.5308P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.047
S = 1.01	Δρmax = 0.27 e Å^−3
8591 reflections	Δρmin = −0.41 e Å^−3
666 parameters

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

	x	y	z	Uiso*/Ueq
Cl1A	0.55936 (7)	0.31031 (6)	0.26676 (7)	0.0770 (3)
N1A	1.20433 (19)	0.49506 (15)	0.26542 (14)	0.0370 (5)
C2A	1.2954 (2)	0.57473 (19)	0.25646 (17)	0.0386 (6)
N3A	1.2412 (2)	0.65972 (16)	0.23397 (15)	0.0441 (5)
C4A	1.1082 (2)	0.6315 (2)	0.22685 (18)	0.0409 (6)
C5A	1.0807 (2)	0.53130 (19)	0.24560 (17)	0.0368 (5)
C6A	0.9566 (2)	0.47466 (18)	0.25115 (16)	0.0347 (5)
C7A	0.8348 (3)	0.5044 (2)	0.20488 (19)	0.0424 (6)
C8A	0.7140 (3)	0.4570 (2)	0.2103 (2)	0.0468 (7)
C9A	0.7111 (2)	0.3747 (2)	0.26089 (19)	0.0441 (6)
C10A	0.8275 (3)	0.3425 (2)	0.3085 (2)	0.0504 (7)
C11A	0.9487 (3)	0.3930 (2)	0.3041 (2)	0.0462 (7)
C12A	1.2323 (3)	0.3870 (2)	0.2733 (3)	0.0530 (8)
N13A	1.4247 (2)	0.5631 (2)	0.2631 (2)	0.0513 (6)
H1A	1.049 (3)	0.680 (2)	0.2111 (17)	0.050 (8)*
H2A	0.841 (2)	0.558 (2)	0.1730 (17)	0.045 (7)*
H3A	0.633 (3)	0.480 (2)	0.175 (2)	0.069 (9)*
H4A	0.825 (3)	0.285 (2)	0.3440 (18)	0.056 (8)*
H5A	1.028 (3)	0.376 (2)	0.342 (2)	0.063 (9)*
H6A	1.302 (3)	0.379 (2)	0.244 (2)	0.078 (10)*
H7A	1.256 (3)	0.375 (3)	0.335 (2)	0.092 (13)*
H8A	1.155 (3)	0.342 (2)	0.2431 (18)	0.054 (8)*
H9A	1.478 (3)	0.622 (2)	0.2612 (17)	0.042 (7)*
H10A	1.459 (3)	0.533 (2)	0.303 (2)	0.058 (10)*
Cl1B	1.28359 (7)	1.12207 (6)	0.24618 (6)	0.0650 (2)
N1B	0.63556 (18)	0.93474 (15)	0.24048 (14)	0.0361 (5)
C2B	0.5429 (2)	0.8526 (2)	0.24325 (17)	0.0396 (6)
N3B	0.5924 (2)	0.76350 (16)	0.25368 (15)	0.0440 (5)
C4B	0.7247 (2)	0.7903 (2)	0.25839 (18)	0.0410 (6)
C5B	0.7558 (2)	0.89446 (18)	0.25041 (16)	0.0347 (5)
C6B	0.8821 (2)	0.95344 (18)	0.24894 (16)	0.0333 (5)
C7B	1.0022 (2)	0.9222 (2)	0.29663 (18)	0.0394 (6)
C8B	1.1248 (3)	0.9717 (2)	0.29509 (19)	0.0424 (6)
C9B	1.1300 (2)	1.05629 (19)	0.24681 (18)	0.0409 (6)
C10B	1.0138 (3)	1.0897 (2)	0.1983 (2)	0.0445 (6)
C11B	0.8915 (2)	1.0375 (2)	0.19894 (18)	0.0403 (6)
C12B	0.6099 (3)	1.0427 (2)	0.2347 (2)	0.0459 (7)
N13B	0.4153 (2)	0.8655 (2)	0.24197 (19)	0.0492 (6)
H1B	0.787 (3)	0.739 (2)	0.2659 (17)	0.050 (7)*
H2B	0.999 (2)	0.8671 (19)	0.3297 (16)	0.039 (7)*
H3B	1.204 (3)	0.949 (2)	0.3284 (18)	0.057 (8)*
H4B	1.018 (2)	1.146 (2)	0.1624 (17)	0.046 (7)*
H5B	0.814 (3)	1.057 (2)	0.1616 (18)	0.051 (8)*
H6B	0.692 (3)	1.091 (2)	0.2642 (18)	0.054 (8)*
H7B	0.543 (3)	1.058 (2)	0.270 (2)	0.071 (9)*
H8B	0.577 (3)	1.051 (3)	0.173 (2)	0.080 (11)*
H9B	0.360 (3)	0.805 (2)	0.2379 (19)	0.059 (9)*
H10B	0.381 (3)	0.907 (2)	0.209 (2)	0.060 (10)*
Cl1C	−0.36805 (6)	0.09608 (5)	0.48288 (5)	0.0554 (2)
N1C	0.29081 (19)	0.27840 (15)	0.51065 (14)	0.0364 (5)
C2C	0.3857 (2)	0.36089 (19)	0.51278 (18)	0.0413 (6)
N3C	0.3458 (2)	0.45333 (16)	0.52289 (17)	0.0490 (6)
C4C	0.2174 (3)	0.4285 (2)	0.5283 (2)	0.0463 (7)
C5C	0.1796 (2)	0.32216 (18)	0.52118 (17)	0.0366 (6)
C6C	0.0498 (2)	0.26253 (18)	0.51368 (16)	0.0343 (5)
C7C	−0.0352 (2)	0.3089 (2)	0.55622 (18)	0.0400 (6)
C8C	−0.1626 (3)	0.2591 (2)	0.54628 (18)	0.0419 (6)
C9C	−0.2075 (2)	0.16042 (19)	0.49546 (17)	0.0372 (6)
C10C	−0.1261 (2)	0.1108 (2)	0.45387 (18)	0.0389 (6)
C11C	0.0007 (2)	0.16222 (19)	0.46294 (17)	0.0374 (6)
C12C	0.3174 (3)	0.1705 (2)	0.5178 (2)	0.0437 (6)
N13C	0.5097 (2)	0.3478 (2)	0.5070 (2)	0.0559 (7)
H1C	0.164 (3)	0.485 (2)	0.5362 (18)	0.054 (8)*
H2C	0.000 (3)	0.374 (2)	0.5951 (19)	0.065 (9)*
H3C	−0.218 (3)	0.292 (2)	0.5777 (19)	0.059 (8)*
H4C	−0.156 (2)	0.0440 (19)	0.4184 (16)	0.039 (7)*
H5C	0.053 (3)	0.128 (2)	0.4305 (18)	0.053 (8)*
H6C	0.307 (3)	0.137 (2)	0.457 (2)	0.072 (10)*
H7C	0.408 (3)	0.174 (2)	0.5552 (19)	0.059 (8)*
H8C	0.260 (3)	0.136 (2)	0.5445 (19)	0.058 (9)*
H9C	0.521 (3)	0.292 (3)	0.483 (2)	0.074 (12)*
H10C	0.557 (3)	0.402 (2)	0.4984 (19)	0.054 (9)*
Cl1D	−0.36700 (6)	0.59721 (5)	0.98807 (6)	0.0573 (2)
N1D	0.29092 (19)	0.77988 (15)	1.01479 (14)	0.0362 (5)
C2D	0.3838 (2)	0.86228 (19)	1.01311 (17)	0.0380 (6)
N3D	0.3418 (2)	0.95447 (16)	1.01906 (15)	0.0425 (5)
C4D	0.2147 (2)	0.93007 (19)	1.02591 (18)	0.0393 (6)
C5D	0.1793 (2)	0.82403 (18)	1.02337 (16)	0.0351 (5)
C6D	0.0498 (2)	0.76419 (18)	1.01751 (16)	0.0342 (5)
C7D	−0.0370 (2)	0.8119 (2)	1.05673 (18)	0.0393 (6)
C8D	−0.1640 (2)	0.7621 (2)	1.04731 (18)	0.0413 (6)
C9D	−0.2067 (2)	0.66113 (19)	0.99986 (17)	0.0383 (6)
C10D	−0.1235 (3)	0.6105 (2)	0.96111 (19)	0.0432 (6)
C11D	0.0030 (3)	0.6621 (2)	0.96967 (18)	0.0410 (6)
C12D	0.3214 (3)	0.6746 (2)	1.0308 (2)	0.0447 (7)
N13D	0.5085 (2)	0.8487 (2)	1.0092 (2)	0.0525 (7)
H1D	0.166 (2)	0.9845 (19)	1.0317 (16)	0.036 (6)*
H2D	−0.003 (2)	0.881 (2)	1.0926 (17)	0.047 (7)*
H3D	−0.218 (3)	0.798 (2)	1.0745 (18)	0.058 (8)*
H4D	−0.152 (2)	0.540 (2)	0.9276 (17)	0.050 (7)*
H5D	0.054 (3)	0.630 (2)	0.9397 (17)	0.046 (7)*
H6D	0.416 (3)	0.679 (2)	1.069 (2)	0.072 (10)*
H7D	0.310 (3)	0.634 (2)	0.976 (2)	0.064 (10)*
H8D	0.261 (3)	0.642 (2)	1.059 (2)	0.066 (9)*
H9D	0.518 (3)	0.792 (3)	0.985 (2)	0.066 (11)*
H10D	0.556 (3)	0.903 (2)	1.0015 (19)	0.052 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0469 (4)	0.0560 (5)	0.1411 (9)	0.0076 (4)	0.0443 (5)	0.0286 (5)
N1A	0.0332 (10)	0.0328 (11)	0.0468 (13)	0.0069 (8)	0.0133 (9)	0.0084 (9)
C2A	0.0369 (13)	0.0361 (13)	0.0448 (15)	0.0057 (10)	0.0153 (11)	0.0068 (11)
N3A	0.0417 (12)	0.0390 (12)	0.0550 (14)	0.0052 (10)	0.0183 (10)	0.0130 (10)
C4A	0.0365 (13)	0.0383 (14)	0.0524 (17)	0.0094 (11)	0.0162 (12)	0.0146 (12)
C5A	0.0365 (13)	0.0363 (13)	0.0390 (14)	0.0076 (10)	0.0125 (11)	0.0063 (11)
C6A	0.0384 (13)	0.0321 (12)	0.0350 (14)	0.0062 (10)	0.0127 (11)	0.0057 (10)
C7A	0.0432 (14)	0.0386 (14)	0.0497 (17)	0.0114 (11)	0.0152 (12)	0.0169 (13)
C8A	0.0361 (14)	0.0477 (16)	0.0584 (18)	0.0109 (12)	0.0133 (13)	0.0127 (13)
C9A	0.0365 (14)	0.0365 (14)	0.0632 (18)	0.0042 (11)	0.0221 (13)	0.0058 (13)
C10A	0.0481 (16)	0.0435 (15)	0.068 (2)	0.0085 (12)	0.0241 (14)	0.0246 (14)
C11A	0.0391 (14)	0.0469 (16)	0.0560 (18)	0.0103 (12)	0.0136 (13)	0.0219 (13)
C12A	0.0471 (17)	0.0376 (16)	0.079 (3)	0.0127 (13)	0.0212 (17)	0.0173 (16)
N13A	0.0383 (13)	0.0478 (15)	0.0716 (19)	0.0081 (12)	0.0193 (13)	0.0170 (14)
Cl1B	0.0395 (4)	0.0490 (4)	0.1100 (7)	0.0010 (3)	0.0300 (4)	0.0124 (4)
N1B	0.0303 (10)	0.0331 (11)	0.0450 (12)	0.0061 (8)	0.0109 (9)	0.0062 (9)
C2B	0.0354 (13)	0.0406 (14)	0.0411 (15)	0.0016 (11)	0.0108 (11)	0.0057 (11)
N3B	0.0383 (12)	0.0387 (12)	0.0571 (15)	0.0056 (9)	0.0162 (10)	0.0120 (11)
C4B	0.0351 (13)	0.0383 (14)	0.0528 (17)	0.0099 (11)	0.0159 (12)	0.0083 (12)
C5B	0.0331 (12)	0.0346 (13)	0.0366 (14)	0.0071 (10)	0.0102 (10)	0.0044 (11)
C6B	0.0333 (12)	0.0333 (13)	0.0336 (13)	0.0059 (10)	0.0106 (10)	0.0028 (10)
C7B	0.0388 (14)	0.0353 (14)	0.0449 (16)	0.0084 (11)	0.0117 (12)	0.0095 (12)
C8B	0.0340 (13)	0.0431 (15)	0.0495 (17)	0.0101 (11)	0.0093 (12)	0.0085 (12)
C9B	0.0335 (13)	0.0346 (13)	0.0551 (17)	0.0024 (10)	0.0172 (12)	−0.0001 (12)
C10B	0.0410 (14)	0.0371 (14)	0.0576 (18)	0.0063 (11)	0.0157 (13)	0.0149 (13)
C11B	0.0333 (13)	0.0417 (14)	0.0464 (16)	0.0085 (11)	0.0095 (12)	0.0128 (12)
C12B	0.0386 (15)	0.0338 (14)	0.064 (2)	0.0086 (12)	0.0113 (14)	0.0077 (13)
N13B	0.0318 (12)	0.0467 (14)	0.0707 (18)	0.0078 (11)	0.0151 (11)	0.0148 (13)
Cl1C	0.0364 (3)	0.0502 (4)	0.0836 (6)	0.0045 (3)	0.0242 (3)	0.0128 (4)
N1C	0.0352 (11)	0.0300 (10)	0.0469 (13)	0.0075 (8)	0.0154 (9)	0.0067 (9)
C2C	0.0371 (13)	0.0338 (14)	0.0519 (17)	0.0044 (11)	0.0121 (12)	0.0061 (12)
N3C	0.0414 (12)	0.0301 (11)	0.0775 (17)	0.0048 (9)	0.0222 (11)	0.0057 (11)
C4C	0.0373 (14)	0.0339 (14)	0.068 (2)	0.0076 (11)	0.0178 (13)	0.0020 (13)
C5C	0.0330 (12)	0.0328 (13)	0.0439 (15)	0.0071 (10)	0.0113 (11)	0.0026 (11)
C6C	0.0342 (12)	0.0317 (12)	0.0383 (14)	0.0075 (10)	0.0114 (11)	0.0070 (10)
C7C	0.0407 (14)	0.0364 (14)	0.0439 (16)	0.0101 (11)	0.0142 (12)	0.0000 (12)
C8C	0.0389 (14)	0.0447 (15)	0.0468 (16)	0.0148 (12)	0.0177 (12)	0.0045 (12)
C9C	0.0316 (12)	0.0380 (13)	0.0454 (15)	0.0087 (10)	0.0136 (11)	0.0124 (11)
C10C	0.0386 (14)	0.0328 (13)	0.0439 (16)	0.0045 (11)	0.0116 (11)	0.0017 (12)
C11C	0.0391 (13)	0.0344 (13)	0.0411 (15)	0.0081 (11)	0.0162 (11)	0.0008 (11)
C12C	0.0443 (16)	0.0336 (14)	0.059 (2)	0.0120 (12)	0.0204 (15)	0.0125 (13)
N13C	0.0410 (13)	0.0396 (15)	0.097 (2)	0.0083 (12)	0.0336 (14)	0.0136 (15)
Cl1D	0.0330 (3)	0.0497 (4)	0.0879 (6)	0.0009 (3)	0.0179 (3)	0.0107 (4)
N1D	0.0346 (11)	0.0311 (10)	0.0465 (13)	0.0052 (8)	0.0171 (9)	0.0079 (9)
C2D	0.0350 (13)	0.0341 (13)	0.0473 (16)	0.0052 (10)	0.0150 (11)	0.0093 (11)
N3D	0.0353 (11)	0.0344 (11)	0.0596 (14)	0.0042 (9)	0.0157 (10)	0.0120 (10)
C4D	0.0355 (13)	0.0302 (13)	0.0552 (17)	0.0078 (10)	0.0154 (12)	0.0111 (12)
C5D	0.0345 (12)	0.0340 (13)	0.0378 (14)	0.0072 (10)	0.0114 (10)	0.0059 (11)
C6D	0.0331 (12)	0.0338 (13)	0.0363 (14)	0.0044 (10)	0.0106 (10)	0.0088 (10)
C7D	0.0390 (13)	0.0332 (13)	0.0462 (16)	0.0059 (11)	0.0154 (12)	0.0001 (12)
C8D	0.0352 (13)	0.0417 (15)	0.0492 (16)	0.0099 (11)	0.0159 (12)	0.0028 (12)
C9D	0.0307 (12)	0.0395 (14)	0.0450 (15)	0.0049 (10)	0.0107 (11)	0.0101 (12)
C10D	0.0408 (14)	0.0352 (14)	0.0504 (17)	−0.0007 (11)	0.0142 (12)	−0.0018 (12)
C11D	0.0392 (14)	0.0397 (14)	0.0469 (16)	0.0044 (11)	0.0202 (12)	−0.0002 (12)
C12D	0.0476 (17)	0.0300 (14)	0.063 (2)	0.0102 (12)	0.0239 (15)	0.0103 (13)
N13D	0.0417 (13)	0.0361 (14)	0.087 (2)	0.0077 (11)	0.0301 (13)	0.0114 (14)

Geometric parameters (Å, º)

Cl1A—C9A	1.740 (3)	Cl1C—C9C	1.740 (2)
N1A—C2A	1.360 (3)	N1C—C2C	1.356 (3)
N1A—C5A	1.400 (3)	N1C—C5C	1.404 (3)
N1A—C12A	1.461 (3)	N1C—C12C	1.455 (3)
C2A—N3A	1.323 (3)	C2C—N3C	1.316 (3)
C2A—N13A	1.367 (3)	C2C—N13C	1.366 (3)
N3A—C4A	1.375 (3)	N3C—C4C	1.382 (3)
C4A—C5A	1.360 (3)	C4C—C5C	1.358 (3)
C4A—H1A	0.93 (3)	C4C—H1C	0.99 (3)
C5A—C6A	1.447 (3)	C5C—C6C	1.454 (3)
C6A—C11A	1.398 (3)	C6C—C11C	1.396 (3)
C6A—C7A	1.398 (3)	C6C—C7C	1.407 (3)
C7A—C8A	1.373 (4)	C7C—C8C	1.375 (4)
C7A—H2A	0.89 (3)	C7C—H2C	0.95 (3)
C8A—C9A	1.374 (4)	C8C—C9C	1.375 (4)
C8A—H3A	0.97 (3)	C8C—H3C	0.98 (3)
C9A—C10A	1.374 (4)	C9C—C10C	1.388 (3)
C10A—C11A	1.384 (4)	C10C—C11C	1.380 (3)
C10A—H4A	0.96 (3)	C10C—H4C	0.94 (2)
C11A—H5A	0.94 (3)	C11C—H5C	0.96 (3)
C12A—H6A	0.98 (3)	C12C—H6C	0.96 (3)
C12A—H7A	0.95 (4)	C12C—H7C	0.96 (3)
C12A—H8A	0.91 (3)	C12C—H8C	0.92 (3)
N13A—H9A	0.89 (3)	N13C—H9C	0.81 (3)
N13A—H10A	0.78 (3)	N13C—H10C	0.85 (3)
Cl1B—C9B	1.737 (3)	Cl1D—C9D	1.738 (2)
N1B—C2B	1.360 (3)	N1D—C2D	1.359 (3)
N1B—C5B	1.402 (3)	N1D—C5D	1.402 (3)
N1B—C12B	1.450 (3)	N1D—C12D	1.454 (3)
C2B—N3B	1.319 (3)	C2D—N3D	1.317 (3)
C2B—N13B	1.371 (3)	C2D—N13D	1.365 (3)
N3B—C4B	1.376 (3)	N3D—C4D	1.376 (3)
C4B—C5B	1.363 (3)	C4D—C5D	1.360 (3)
C4B—H1B	0.97 (3)	C4D—H1D	0.93 (2)
C5B—C6B	1.457 (3)	C5D—C6D	1.457 (3)
C6B—C11B	1.395 (3)	C6D—C11D	1.397 (3)
C6B—C7B	1.399 (3)	C6D—C7D	1.401 (3)
C7B—C8B	1.378 (4)	C7D—C8D	1.373 (3)
C7B—H2B	0.91 (2)	C7D—H2D	0.96 (3)
C8B—C9B	1.379 (4)	C8D—C9D	1.380 (4)
C8B—H3B	0.95 (3)	C8D—H3D	0.93 (3)
C9B—C10B	1.384 (4)	C9D—C10D	1.384 (3)
C10B—C11B	1.383 (4)	C10D—C11D	1.380 (4)
C10B—H4B	0.96 (3)	C10D—H4D	0.96 (3)
C11B—H5B	0.94 (3)	C11D—H5D	0.92 (3)
C12B—H6B	0.96 (3)	C12D—H6D	0.99 (3)
C12B—H7B	1.04 (3)	C12D—H7D	0.92 (3)
C12B—H8B	0.93 (3)	C12D—H8D	0.95 (3)
N13B—H9B	0.89 (3)	N13D—H9D	0.82 (3)
N13B—H10B	0.82 (3)	N13D—H10D	0.85 (3)
C2A—N1A—C5A	107.06 (19)	C2C—N1C—C5C	106.64 (19)
C2A—N1A—C12A	122.8 (2)	C2C—N1C—C12C	123.5 (2)
C5A—N1A—C12A	128.7 (2)	C5C—N1C—C12C	128.4 (2)
N3A—C2A—N1A	112.2 (2)	N3C—C2C—N1C	112.7 (2)
N3A—C2A—N13A	125.0 (2)	N3C—C2C—N13C	124.5 (2)
N1A—C2A—N13A	122.7 (2)	N1C—C2C—N13C	122.8 (2)
C2A—N3A—C4A	104.3 (2)	C2C—N3C—C4C	104.3 (2)
C5A—C4A—N3A	112.4 (2)	C5C—C4C—N3C	111.9 (2)
C5A—C4A—H1A	127.8 (16)	C5C—C4C—H1C	127.1 (16)
N3A—C4A—H1A	119.9 (16)	N3C—C4C—H1C	121.0 (16)
C4A—C5A—N1A	104.1 (2)	C4C—C5C—N1C	104.4 (2)
C4A—C5A—C6A	129.6 (2)	C4C—C5C—C6C	129.6 (2)
N1A—C5A—C6A	126.2 (2)	N1C—C5C—C6C	125.5 (2)
C11A—C6A—C7A	116.0 (2)	C11C—C6C—C7C	117.1 (2)
C11A—C6A—C5A	124.2 (2)	C11C—C6C—C5C	123.7 (2)
C7A—C6A—C5A	119.7 (2)	C7C—C6C—C5C	119.1 (2)
C8A—C7A—C6A	122.7 (2)	C8C—C7C—C6C	121.6 (2)
C8A—C7A—H2A	121.6 (16)	C8C—C7C—H2C	120.6 (17)
C6A—C7A—H2A	115.7 (16)	C6C—C7C—H2C	117.7 (17)
C7A—C8A—C9A	119.2 (2)	C7C—C8C—C9C	119.6 (2)
C7A—C8A—H3A	118.7 (18)	C7C—C8C—H3C	119.7 (16)
C9A—C8A—H3A	122.1 (18)	C9C—C8C—H3C	120.6 (16)
C10A—C9A—C8A	120.8 (2)	C8C—C9C—C10C	120.8 (2)
C10A—C9A—Cl1A	118.8 (2)	C8C—C9C—Cl1C	120.09 (19)
C8A—C9A—Cl1A	120.4 (2)	C10C—C9C—Cl1C	119.14 (19)
C9A—C10A—C11A	119.2 (3)	C11C—C10C—C9C	119.2 (2)
C9A—C10A—H4A	120.3 (16)	C11C—C10C—H4C	119.2 (15)
C11A—C10A—H4A	120.4 (16)	C9C—C10C—H4C	121.5 (15)
C10A—C11A—C6A	122.1 (2)	C10C—C11C—C6C	121.7 (2)
C10A—C11A—H5A	118.4 (18)	C10C—C11C—H5C	117.3 (16)
C6A—C11A—H5A	119.3 (18)	C6C—C11C—H5C	120.9 (16)
N1A—C12A—H6A	105.7 (19)	N1C—C12C—H6C	107.3 (18)
N1A—C12A—H7A	111 (2)	N1C—C12C—H7C	108.3 (17)
H6A—C12A—H7A	114 (3)	H6C—C12C—H7C	110 (2)
N1A—C12A—H8A	107.0 (17)	N1C—C12C—H8C	109.6 (17)
H6A—C12A—H8A	112 (3)	H6C—C12C—H8C	112 (3)
H7A—C12A—H8A	108 (3)	H7C—C12C—H8C	110 (2)
C2A—N13A—H9A	115.4 (16)	C2C—N13C—H9C	120 (2)
C2A—N13A—H10A	115 (2)	C2C—N13C—H10C	116.3 (19)
H9A—N13A—H10A	111 (3)	H9C—N13C—H10C	114 (3)
C2B—N1B—C5B	106.56 (19)	C2D—N1D—C5D	106.24 (19)
C2B—N1B—C12B	124.0 (2)	C2D—N1D—C12D	123.7 (2)
C5B—N1B—C12B	129.3 (2)	C5D—N1D—C12D	127.9 (2)
N3B—C2B—N1B	112.7 (2)	N3D—C2D—N1D	112.8 (2)
N3B—C2B—N13B	124.9 (2)	N3D—C2D—N13D	124.9 (2)
N1B—C2B—N13B	122.3 (2)	N1D—C2D—N13D	122.2 (2)
C2B—N3B—C4B	104.3 (2)	C2D—N3D—C4D	104.4 (2)
C5B—C4B—N3B	112.0 (2)	C5D—C4D—N3D	111.8 (2)
C5B—C4B—H1B	125.2 (15)	C5D—C4D—H1D	129.0 (15)
N3B—C4B—H1B	122.7 (15)	N3D—C4D—H1D	119.2 (15)
C4B—C5B—N1B	104.4 (2)	C4D—C5D—N1D	104.8 (2)
C4B—C5B—C6B	129.5 (2)	C4D—C5D—C6D	129.4 (2)
N1B—C5B—C6B	126.0 (2)	N1D—C5D—C6D	125.4 (2)
C11B—C6B—C7B	117.0 (2)	C11D—C6D—C7D	117.2 (2)
C11B—C6B—C5B	123.9 (2)	C11D—C6D—C5D	123.2 (2)
C7B—C6B—C5B	119.1 (2)	C7D—C6D—C5D	119.5 (2)
C8B—C7B—C6B	122.0 (2)	C8D—C7D—C6D	121.8 (2)
C8B—C7B—H2B	119.1 (15)	C8D—C7D—H2D	120.7 (15)
C6B—C7B—H2B	118.9 (15)	C6D—C7D—H2D	117.4 (15)
C7B—C8B—C9B	119.2 (2)	C7D—C8D—C9D	119.4 (2)
C7B—C8B—H3B	119.9 (17)	C7D—C8D—H3D	118.2 (17)
C9B—C8B—H3B	120.9 (17)	C9D—C8D—H3D	122.3 (17)
C8B—C9B—C10B	120.8 (2)	C8D—C9D—C10D	120.6 (2)
C8B—C9B—Cl1B	120.02 (19)	C8D—C9D—Cl1D	119.71 (19)
C10B—C9B—Cl1B	119.2 (2)	C10D—C9D—Cl1D	119.7 (2)
C11B—C10B—C9B	119.2 (2)	C11D—C10D—C9D	119.4 (2)
C11B—C10B—H4B	120.3 (15)	C11D—C10D—H4D	119.0 (15)
C9B—C10B—H4B	120.4 (15)	C9D—C10D—H4D	121.6 (15)
C10B—C11B—C6B	121.8 (2)	C10D—C11D—C6D	121.5 (2)
C10B—C11B—H5B	117.9 (16)	C10D—C11D—H5D	118.6 (16)
C6B—C11B—H5B	120.3 (16)	C6D—C11D—H5D	119.8 (16)
N1B—C12B—H6B	109.4 (16)	N1D—C12D—H6D	110.2 (17)
N1B—C12B—H7B	109.5 (16)	N1D—C12D—H7D	109.4 (19)
H6B—C12B—H7B	107 (2)	H6D—C12D—H7D	108 (2)
N1B—C12B—H8B	109 (2)	N1D—C12D—H8D	109.1 (17)
H6B—C12B—H8B	111 (3)	H6D—C12D—H8D	112 (2)
H7B—C12B—H8B	112 (3)	H7D—C12D—H8D	108 (3)
C2B—N13B—H9B	114.8 (18)	C2D—N13D—H9D	118 (2)
C2B—N13B—H10B	116 (2)	C2D—N13D—H10D	115.2 (19)
H9B—N13B—H10B	114 (3)	H9D—N13D—H10D	116 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13C—H10C···N3C^i	0.85 (3)	2.11 (3)	2.955 (3)	173 (3)
N13D—H10D···N3D^ii	0.85 (3)	2.11 (3)	2.949 (3)	175 (3)
N13A—H9A···N3B^iii	0.89 (3)	2.09 (3)	2.979 (4)	176 (2)
N13B—H9B···N3A^iv	0.89 (3)	2.11 (3)	2.998 (3)	176 (3)
N13C—H9C···Cl1C^iii	0.81 (4)	2.90 (4)	3.646 (3)	154 (3)
N13D—H9D···Cl1D^iii	0.82 (3)	2.91 (4)	3.650 (3)	152 (3)
N13A—H10A···Cl1A^iii	0.78 (3)	3.21 (3)	3.696 (3)	122 (3)
N13B—H10B···Cl1B^iv	0.82 (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) x−1, y, z.