organic compounds
The asymmetric unit of the title compound, C10H10ClN3, contains four independent molecules, two of which are related by a pseudo-inversion centre. Intermolecular N—HN and N—HCl interactions are present in the crystal.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000284/dn6007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000284/dn6007Isup2.hkl |
CCDC reference: 180781
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
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) Å3 |
Data collection top
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 top
Refinement on F2 | All 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 = 1.01 | 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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N13C—H10C···N3Ci | 0.85 (3) | 2.11 (3) | 2.955 (3) | 173 (3) |
N13D—H10D···N3Dii | 0.85 (3) | 2.11 (3) | 2.949 (3) | 175 (3) |
N13A—H9A···N3Biii | 0.89 (3) | 2.09 (3) | 2.979 (4) | 176 (2) |
N13B—H9B···N3Aiv | 0.89 (3) | 2.11 (3) | 2.998 (3) | 176 (3) |
N13C—H9C···Cl1Ciii | 0.81 (4) | 2.90 (4) | 3.646 (3) | 154 (3) |
N13D—H9D···Cl1Diii | 0.82 (3) | 2.91 (4) | 3.650 (3) | 152 (3) |
N13A—H10A···Cl1Aiii | 0.78 (3) | 3.21 (3) | 3.696 (3) | 122 (3) |
N13B—H10B···Cl1Biv | 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. |