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organic compounds
The title compound, C23H19ClN2O, crystallizes as a racemic mixture having two molecules in the asymmetric unit. The structure is disordered.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007220/na6218sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007220/na6218Isup2.hkl |
CCDC reference: 214595
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(Please check) = 0.000 Å
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Experimental top
A solution of 2,4-diphenyl-1,5-benzodiazepina (2.0 mmol) and chloroacetyl chloride (2.0 mmol) in 20 ml of anhydrous benzene was stirred at room temperature for 3 h. After the solvent was removed, the title compound was separated by column chromatography on silica gel, using chloroform as eluent, and obtained as yellow crystals after solvent evaporation (yield 90%, m.p. 449 K), which were suitable for X-ray diffraction. Analysis calculated for C23H19ClN2O: C 73.69, H 5.11, N 7.47%; found: C 73.78, H 5.17, N 7.42%.
Refinement top
The title compound crystallized in the monoclinic system; space group Cc was assumed and confirmed by the analysis. H atoms were treated as riding atoms with aromatic C—H = 0.95 Å, CH2 C—H = 0.99 Å (CH2) and CH C—H = 1.00 Å (CH). The structure initially refined to an R of 9.55% but the difference map showed several high peaks, the highest two being 1.60 and 1.59 e Å−3. A map of the highest 30 peaks showed two diazepine rings with the attached Cl side chain, the highest peaks mentioned above being the Cl atoms; however, only fragments of the attached phenyl groups could be located. The coordinates of the peaks which could be found indicated that disordered molecules were present with coordinates x, −y, z with respect to those of the major component molecules. Refinement of a group site-occupancy factor for the major component gave a value of 0.92, which is in agreement with the height of the highest peaks in the difference map. By varying the value of the site-occupancy factor around this value after the final refinement it was found that this value lay within the optimal range as far as low R factor was concerned and so the refinement was carried out with the fixed values of 0.92 (0.08) for the site-occupancy factors of the major (minor) components. The minor component was created by taking the atoms in the major component, changing the sign of the y coordinates and adding a shift of 1 to them to bring the disordered molecules into the unit cell. The atoms of the minor components were made isotropic. Attempts at refinement lead to instability so the minor component was fixed by an overall AFIX 1. The process was repeated several times with the minor component being refreshed after several cycles of least squares. The R factor dropped to 6.85%.
Computing details top
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Figures top
![[Figure 1]](http://journals.iucr.org/e/issues/2003/05/00/na6218/na6218fig1thm.gif)
| Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](http://journals.iucr.org/e/issues/2003/05/00/na6218/na6218fig2thm.gif)
| Fig. 2. A view of the crystal structure, showing the C22(8) chain which runs parallel to the b axis. All H atoms not involved in hydrogen bonding and the unit cell have been omitted for the sake of clarity. The molecules labelled with an asterisk (*) are a (x, y − 1, z) and those labelled with a hash (#) are at (x, y + 1, z). |
![[Figure 3]](http://journals.iucr.org/e/issues/2003/05/00/na6218/na6218fig3thm.gif)
| Fig. 3. A view of the crystal structure, showing the C(9) chain involving molecules of the R conformer which runs parallel to the c axis. A similar chain links molecules of type 2 together. The molecule labelled with an asterisk (*) is at (x, 2 − y, z − 0.5) and that labelled with a hash (#) is at (x, 2 − y, z + 0.5). |
2-chloro-1-(2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)-1-ethanone top
Crystal data top
| C23H19ClN2O | F(000) = 1568 |
| Mr = 374.85 | Dx = 1.345 Mg m−3 |
| Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
| a = 31.7081 (8) Å | Cell parameters from 7396 reflections |
| b = 7.8174 (2) Å | θ = 2.9–27.3° |
| c = 15.4208 (5) Å | µ = 0.22 mm−1 |
| β = 104.344 (1)° | T = 120 K |
| V = 3703.27 (18) Å3 | Plate, colourless |
| Z = 8 | 0.36 × 0.12 × 0.08 mm |
Data collection top
| Nonius KappaCCD diffractometer | 7396 independent reflections |
| Radiation source: fine-focus sealed X-ray tube | 5168 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.095 |
| ϕ scans and ω scans with κ offsets | θmax = 27.3°, θmin = 2.9° |
| Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −40→40 |
| Tmin = 0.925, Tmax = 0.983 | k = −10→7 |
| 17924 measured reflections | l = −19→19 |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.069 | w = 1/[σ2(Fo2) + (0.1033P)2 + 1.4124P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.201 | (Δ/σ)max = 0.001 |
| S = 1.04 | Δρmax = 0.40 e Å−3 |
| 7396 reflections | Δρmin = −0.40 e Å−3 |
| 488 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 2 restraints | Extinction coefficient: 0.0041 (7) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 4142 Friedel pairs |
| Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.09 (10) |
Crystal data top
| C23H19ClN2O | V = 3703.27 (18) Å3 |
| Mr = 374.85 | Z = 8 |
| Monoclinic, Cc | Mo Kα radiation |
| a = 31.7081 (8) Å | µ = 0.22 mm−1 |
| b = 7.8174 (2) Å | T = 120 K |
| c = 15.4208 (5) Å | 0.36 × 0.12 × 0.08 mm |
| β = 104.344 (1)° |
Data collection top
| Nonius KappaCCD diffractometer | 7396 independent reflections |
| Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 5168 reflections with I > 2σ(I) |
| Tmin = 0.925, Tmax = 0.983 | Rint = 0.095 |
| 17924 measured reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
| wR(F2) = 0.201 | Δρmax = 0.40 e Å−3 |
| S = 1.04 | Δρmin = −0.40 e Å−3 |
| 7396 reflections | Absolute structure: Flack (1983), 4142 Friedel pairs |
| 488 parameters | Absolute structure parameter: 0.09 (10) |
| 2 restraints |
Special details top
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. reference: Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886–891. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| N11 | 0.2224 (5) | 0.7288 (5) | 0.1971 (8) | 0.0226 (8) | 0.92 |
| C121 | 0.2588 (5) | 0.6779 (7) | 0.2608 (8) | 0.0261 (10) | 0.92 |
| O12 | 0.2864 (5) | 0.7799 (4) | 0.2981 (8) | 0.0312 (8) | 0.92 |
| C122 | 0.2632 (5) | 0.4911 (6) | 0.2851 (8) | 0.0339 (12) | 0.92 |
| Cl11 | 0.2304 (5) | 0.4444 (2) | 0.3604 (8) | 0.0581 (5) | 0.92 |
| C11A | 0.1908 (5) | 0.6132 (6) | 0.1476 (8) | 0.0251 (10) | 0.92 |
| C12 | 0.2006 (5) | 0.5055 (6) | 0.0844 (8) | 0.0341 (12) | 0.92 |
| C13 | 0.1701 (5) | 0.3906 (7) | 0.0363 (8) | 0.0349 (12) | 0.92 |
| C14 | 0.1289 (5) | 0.3863 (7) | 0.0527 (8) | 0.0370 (13) | 0.92 |
| C15 | 0.1182 (5) | 0.4900 (6) | 0.1162 (8) | 0.0282 (11) | 0.92 |
| C15A | 0.1492 (5) | 0.6100 (6) | 0.1627 (8) | 0.0264 (10) | 0.92 |
| N16 | 0.1366 (5) | 0.7169 (5) | 0.2266 (8) | 0.0260 (9) | 0.92 |
| C17 | 0.1448 (5) | 0.8780 (6) | 0.2252 (8) | 0.0246 (10) | 0.92 |
| C171 | 0.1332 (5) | 0.9897 (6) | 0.2935 (8) | 0.0226 (10) | 0.92 |
| C172 | 0.1402 (5) | 1.1664 (7) | 0.2952 (8) | 0.0308 (11) | 0.92 |
| C173 | 0.1273 (5) | 1.2683 (7) | 0.3574 (8) | 0.0326 (12) | 0.92 |
| C174 | 0.1067 (5) | 1.1964 (7) | 0.4178 (8) | 0.0328 (12) | 0.92 |
| C175 | 0.0999 (5) | 1.0218 (7) | 0.4172 (8) | 0.0295 (11) | 0.92 |
| C176 | 0.1129 (5) | 0.9205 (6) | 0.3551 (8) | 0.0266 (11) | 0.92 |
| C18 | 0.1670 (5) | 0.9533 (6) | 0.1569 (8) | 0.0247 (10) | 0.92 |
| C19 | 0.2158 (5) | 0.9175 (6) | 0.1837 (8) | 0.0247 (10) | 0.92 |
| C191 | 0.2407 (5) | 0.9910 (6) | 0.1212 (8) | 0.0240 (10) | 0.92 |
| C192 | 0.2745 (5) | 1.1044 (6) | 0.1539 (8) | 0.0256 (10) | 0.92 |
| C193 | 0.2970 (5) | 1.1768 (7) | 0.0964 (8) | 0.0351 (12) | 0.92 |
| C194 | 0.2868 (5) | 1.1362 (7) | 0.0078 (8) | 0.0346 (12) | 0.92 |
| C195 | 0.2530 (5) | 1.0232 (7) | −0.0259 (8) | 0.0376 (13) | 0.92 |
| C196 | 0.2300 (5) | 0.9504 (7) | 0.0299 (8) | 0.0304 (11) | 0.92 |
| N21 | 0.4134 (5) | 0.2318 (5) | 0.2935 (8) | 0.0236 (8) | 0.92 |
| C221 | 0.3774 (5) | 0.1799 (7) | 0.3196 (8) | 0.0279 (11) | 0.92 |
| O22 | 0.3491 (5) | 0.2805 (4) | 0.3292 (8) | 0.0316 (8) | 0.92 |
| C222 | 0.3731 (5) | −0.0067 (7) | 0.3408 (8) | 0.0346 (12) | 0.92 |
| Cl21 | 0.4060 (5) | −0.0534 (2) | 0.4495 (8) | 0.0626 (5) | 0.92 |
| C21A | 0.4452 (5) | 0.1154 (6) | 0.2756 (8) | 0.0257 (10) | 0.92 |
| C22 | 0.4348 (5) | 0.0076 (7) | 0.2023 (8) | 0.0321 (12) | 0.92 |
| C23 | 0.4656 (5) | −0.1069 (7) | 0.1858 (8) | 0.0339 (12) | 0.92 |
| C24 | 0.5069 (5) | −0.1102 (7) | 0.2414 (8) | 0.0375 (13) | 0.92 |
| C25 | 0.5176 (5) | 0.0003 (7) | 0.3154 (8) | 0.0323 (12) | 0.92 |
| C25A | 0.4870 (5) | 0.1149 (6) | 0.3317 (8) | 0.0248 (10) | 0.92 |
| N26 | 0.5000 (5) | 0.2241 (5) | 0.4074 (8) | 0.0276 (9) | 0.92 |
| C27 | 0.4902 (5) | 0.3849 (6) | 0.3982 (8) | 0.0225 (10) | 0.92 |
| C271 | 0.5023 (5) | 0.4948 (6) | 0.4791 (8) | 0.0258 (11) | 0.92 |
| C272 | 0.5209 (5) | 0.4204 (6) | 0.5620 (8) | 0.0288 (11) | 0.92 |
| C273 | 0.5343 (5) | 0.5227 (6) | 0.6375 (8) | 0.0286 (11) | 0.92 |
| C274 | 0.5289 (5) | 0.6986 (6) | 0.6320 (8) | 0.0320 (12) | 0.92 |
| C275 | 0.5090 (5) | 0.7725 (7) | 0.5505 (8) | 0.0365 (13) | 0.92 |
| C276 | 0.4962 (5) | 0.6710 (7) | 0.4752 (8) | 0.0291 (11) | 0.92 |
| C28 | 0.4678 (5) | 0.4579 (6) | 0.3087 (8) | 0.0256 (10) | 0.92 |
| C29 | 0.4189 (5) | 0.4197 (6) | 0.2867 (8) | 0.0259 (10) | 0.92 |
| C291 | 0.3940 (5) | 0.4927 (6) | 0.1981 (8) | 0.0230 (10) | 0.92 |
| C292 | 0.3602 (5) | 0.6045 (6) | 0.1960 (8) | 0.0273 (11) | 0.92 |
| C293 | 0.3371 (5) | 0.6799 (7) | 0.1161 (8) | 0.0344 (12) | 0.92 |
| C294 | 0.3473 (5) | 0.6368 (7) | 0.0371 (8) | 0.0368 (13) | 0.92 |
| C295 | 0.3814 (5) | 0.5221 (7) | 0.0373 (8) | 0.0371 (13) | 0.92 |
| C296 | 0.4045 (5) | 0.4511 (7) | 0.1173 (8) | 0.0289 (11) | 0.92 |
| N31 | 0.2233 | 0.2712 | 0.2045 | 0.023* | 0.08 |
| C321 | 0.2597 | 0.3222 | 0.2683 | 0.026* | 0.08 |
| O32 | 0.2873 | 0.2202 | 0.3055 | 0.031* | 0.08 |
| C322 | 0.2642 | 0.5090 | 0.2925 | 0.035* | 0.08 |
| Cl31 | 0.2313 | 0.5557 | 0.3678 | 0.058* | 0.08 |
| C31A | 0.1917 | 0.3868 | 0.1550 | 0.025* | 0.08 |
| C32 | 0.2015 | 0.4947 | 0.0918 | 0.034* | 0.08 |
| C33 | 0.1710 | 0.6093 | 0.0437 | 0.035* | 0.08 |
| C34 | 0.1298 | 0.6137 | 0.0601 | 0.037* | 0.08 |
| C35 | 0.1191 | 0.5100 | 0.1234 | 0.029* | 0.08 |
| C35A | 0.1502 | 0.3900 | 0.1701 | 0.026* | 0.08 |
| N36 | 0.1375 | 0.2832 | 0.2340 | 0.026* | 0.08 |
| C37 | 0.1458 | 0.1219 | 0.2326 | 0.025* | 0.08 |
| C371 | 0.1341 | 0.0105 | 0.3008 | 0.023* | 0.08 |
| C372 | 0.1411 | −0.1663 | 0.3026 | 0.031* | 0.08 |
| C373 | 0.1282 | −0.2682 | 0.3648 | 0.033* | 0.08 |
| C374 | 0.1076 | −0.1964 | 0.4252 | 0.033* | 0.08 |
| C375 | 0.1008 | −0.0219 | 0.4246 | 0.030* | 0.08 |
| C376 | 0.1138 | 0.0796 | 0.3625 | 0.027* | 0.08 |
| C38 | 0.1679 | 0.0465 | 0.1643 | 0.025* | 0.08 |
| C39 | 0.2167 | 0.0826 | 0.1911 | 0.024* | 0.08 |
| C391 | 0.2416 | 0.0090 | 0.1285 | 0.025* | 0.08 |
| C392 | 0.2754 | −0.1043 | 0.1613 | 0.026* | 0.08 |
| C393 | 0.2979 | −0.1768 | 0.1038 | 0.035* | 0.08 |
| C394 | 0.2877 | −0.1361 | 0.0152 | 0.034* | 0.08 |
| C395 | 0.2539 | −0.0230 | −0.0185 | 0.038* | 0.08 |
| C396 | 0.2309 | 0.0496 | 0.0372 | 0.030* | 0.08 |
| N41 | 0.4143 | 0.7682 | 0.3009 | 0.024* | 0.08 |
| C421 | 0.3783 | 0.8202 | 0.3271 | 0.028* | 0.08 |
| O42 | 0.3501 | 0.7195 | 0.3367 | 0.032* | 0.08 |
| C422 | 0.3740 | 1.0066 | 0.3481 | 0.036* | 0.08 |
| Cl41 | 0.4069 | 1.0536 | 0.4569 | 0.062* | 0.08 |
| C41A | 0.4461 | 0.8846 | 0.2831 | 0.026* | 0.08 |
| C42 | 0.4357 | 0.9925 | 0.2097 | 0.032* | 0.08 |
| C43 | 0.4665 | 1.1069 | 0.1932 | 0.034* | 0.08 |
| C44 | 0.5078 | 1.1103 | 0.2488 | 0.037* | 0.08 |
| C45 | 0.5185 | 0.9997 | 0.3227 | 0.033* | 0.08 |
| C45A | 0.4879 | 0.8850 | 0.3390 | 0.025* | 0.08 |
| N46 | 0.5010 | 0.7759 | 0.4149 | 0.028* | 0.08 |
| C47 | 0.4911 | 0.6151 | 0.4056 | 0.022* | 0.08 |
| C471 | 0.5032 | 0.5053 | 0.4864 | 0.027* | 0.08 |
| C472 | 0.5218 | 0.5797 | 0.5694 | 0.029* | 0.08 |
| C473 | 0.5352 | 0.4773 | 0.6448 | 0.029* | 0.08 |
| C474 | 0.5298 | 0.3015 | 0.6394 | 0.032* | 0.08 |
| C475 | 0.5100 | 0.2275 | 0.5579 | 0.036* | 0.08 |
| C476 | 0.4971 | 0.3290 | 0.4826 | 0.029* | 0.08 |
| C48 | 0.4687 | 0.5421 | 0.3161 | 0.026* | 0.08 |
| C49 | 0.4198 | 0.5803 | 0.2942 | 0.026* | 0.08 |
| C491 | 0.3948 | 0.5073 | 0.2053 | 0.024* | 0.08 |
| C492 | 0.3611 | 0.3955 | 0.2034 | 0.027* | 0.08 |
| C493 | 0.3380 | 0.3201 | 0.1235 | 0.034* | 0.08 |
| C494 | 0.3483 | 0.3633 | 0.0446 | 0.037* | 0.08 |
| C495 | 0.3823 | 0.4780 | 0.0447 | 0.038* | 0.08 |
| C496 | 0.4054 | 0.5488 | 0.1247 | 0.029* | 0.08 |
| H12A | 0.2940 | 0.4639 | 0.3136 | 0.041* | 0.92 |
| H12B | 0.2538 | 0.4204 | 0.2305 | 0.041* | 0.92 |
| H12 | 0.2288 | 0.5099 | 0.0735 | 0.041* | 0.92 |
| H13 | 0.1773 | 0.3168 | −0.0069 | 0.042* | 0.92 |
| H14 | 0.1076 | 0.3100 | 0.0194 | 0.044* | 0.92 |
| H15 | 0.0904 | 0.4814 | 0.1286 | 0.034* | 0.92 |
| H172 | 0.1539 | 1.2169 | 0.2533 | 0.037* | 0.92 |
| H173 | 0.1326 | 1.3880 | 0.3585 | 0.039* | 0.92 |
| H174 | 0.0972 | 1.2668 | 0.4596 | 0.039* | 0.92 |
| H175 | 0.0864 | 0.9714 | 0.4595 | 0.035* | 0.92 |
| H176 | 0.1077 | 0.8008 | 0.3546 | 0.032* | 0.92 |
| H18A | 0.1620 | 1.0784 | 0.1526 | 0.030* | 0.92 |
| H18B | 0.1541 | 0.9028 | 0.0973 | 0.030* | 0.92 |
| H19 | 0.2275 | 0.9726 | 0.2433 | 0.030* | 0.92 |
| H192 | 0.2822 | 1.1326 | 0.2157 | 0.031* | 0.92 |
| H193 | 0.3199 | 1.2556 | 0.1192 | 0.042* | 0.92 |
| H194 | 0.3027 | 1.1851 | −0.0308 | 0.042* | 0.92 |
| H195 | 0.2456 | 0.9956 | −0.0878 | 0.045* | 0.92 |
| H196 | 0.2069 | 0.8728 | 0.0063 | 0.037* | 0.92 |
| H22A | 0.3823 | −0.0784 | 0.2959 | 0.042* | 0.92 |
| H22B | 0.3423 | −0.0334 | 0.3383 | 0.042* | 0.92 |
| H22 | 0.4065 | 0.0117 | 0.1630 | 0.038* | 0.92 |
| H23 | 0.4580 | −0.1827 | 0.1362 | 0.041* | 0.92 |
| H24 | 0.5281 | −0.1869 | 0.2297 | 0.045* | 0.92 |
| H25 | 0.5460 | −0.0032 | 0.3545 | 0.039* | 0.92 |
| H272 | 0.5244 | 0.2998 | 0.5668 | 0.035* | 0.92 |
| H273 | 0.5473 | 0.4714 | 0.6935 | 0.034* | 0.92 |
| H274 | 0.5387 | 0.7678 | 0.6837 | 0.038* | 0.92 |
| H275 | 0.5043 | 0.8926 | 0.5464 | 0.044* | 0.92 |
| H276 | 0.4828 | 0.7228 | 0.4195 | 0.035* | 0.92 |
| H28A | 0.4805 | 0.4078 | 0.2619 | 0.031* | 0.92 |
| H28B | 0.4724 | 0.5832 | 0.3091 | 0.031* | 0.92 |
| H29 | 0.4071 | 0.4742 | 0.3344 | 0.031* | 0.92 |
| H292 | 0.3523 | 0.6310 | 0.2501 | 0.033* | 0.92 |
| H293 | 0.3146 | 0.7600 | 0.1162 | 0.041* | 0.92 |
| H294 | 0.3312 | 0.6849 | −0.0177 | 0.044* | 0.92 |
| H295 | 0.3886 | 0.4934 | −0.0172 | 0.045* | 0.92 |
| H296 | 0.4276 | 0.3737 | 0.1176 | 0.035* | 0.92 |
| H32A | 0.2950 | 0.5361 | 0.3210 | 0.041* | 0.08 |
| H32B | 0.2548 | 0.5796 | 0.2378 | 0.041* | 0.08 |
| H32 | 0.2297 | 0.4903 | 0.0809 | 0.041* | 0.08 |
| H33 | 0.1782 | 0.6832 | 0.0006 | 0.042* | 0.08 |
| H34 | 0.1086 | 0.6901 | 0.0268 | 0.044* | 0.08 |
| H35 | 0.0913 | 0.5185 | 0.1358 | 0.034* | 0.08 |
| H372 | 0.1549 | −0.2169 | 0.2607 | 0.037* | 0.08 |
| H373 | 0.1336 | −0.3879 | 0.3660 | 0.039* | 0.08 |
| H374 | 0.0981 | −0.2668 | 0.4669 | 0.039* | 0.08 |
| H375 | 0.0873 | 0.0285 | 0.4668 | 0.036* | 0.08 |
| H376 | 0.1086 | 0.1993 | 0.3621 | 0.032* | 0.08 |
| H38A | 0.1629 | −0.0785 | 0.1601 | 0.030* | 0.08 |
| H38B | 0.1551 | 0.0969 | 0.1047 | 0.030* | 0.08 |
| H39 | 0.2284 | 0.0274 | 0.2507 | 0.029* | 0.08 |
| H392 | 0.2831 | −0.1326 | 0.2231 | 0.031* | 0.08 |
| H393 | 0.3208 | −0.2556 | 0.1266 | 0.042* | 0.08 |
| H394 | 0.3036 | −0.1851 | −0.0234 | 0.041* | 0.08 |
| H395 | 0.2466 | 0.0048 | −0.0804 | 0.045* | 0.08 |
| H396 | 0.2078 | 0.1271 | 0.0136 | 0.036* | 0.08 |
| H42A | 0.3832 | 1.0782 | 0.3032 | 0.043* | 0.08 |
| H42B | 0.3432 | 1.0334 | 0.3455 | 0.043* | 0.08 |
| H42 | 0.4075 | 0.9884 | 0.1704 | 0.038* | 0.08 |
| H43 | 0.4589 | 1.1828 | 0.1436 | 0.041* | 0.08 |
| H44 | 0.5290 | 1.1870 | 0.2372 | 0.045* | 0.08 |
| H45 | 0.5469 | 1.0032 | 0.3617 | 0.040* | 0.08 |
| H472 | 0.5253 | 0.7003 | 0.5743 | 0.034* | 0.08 |
| H473 | 0.5483 | 0.5286 | 0.7009 | 0.034* | 0.08 |
| H474 | 0.5396 | 0.2323 | 0.6911 | 0.038* | 0.08 |
| H475 | 0.5052 | 0.1075 | 0.5537 | 0.043* | 0.08 |
| H476 | 0.4837 | 0.2770 | 0.4269 | 0.035* | 0.08 |
| H48A | 0.4814 | 0.5921 | 0.2693 | 0.031* | 0.08 |
| H48B | 0.4733 | 0.4168 | 0.3166 | 0.031* | 0.08 |
| H49 | 0.4080 | 0.5258 | 0.3419 | 0.031* | 0.08 |
| H492 | 0.3533 | 0.3690 | 0.2576 | 0.033* | 0.08 |
| H493 | 0.3155 | 0.2400 | 0.1236 | 0.041* | 0.08 |
| H494 | 0.3322 | 0.3151 | −0.0102 | 0.044* | 0.08 |
| H495 | 0.3895 | 0.5069 | −0.0098 | 0.045* | 0.08 |
| H496 | 0.4286 | 0.6261 | 0.1250 | 0.034* | 0.08 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N11 | 0.0248 (19) | 0.026 (2) | 0.0182 (19) | 0.0030 (16) | 0.0071 (16) | 0.0037 (15) |
| C121 | 0.021 (2) | 0.041 (3) | 0.019 (2) | 0.001 (2) | 0.0103 (19) | 0.003 (2) |
| O12 | 0.0233 (18) | 0.037 (2) | 0.0307 (19) | −0.0030 (16) | 0.0025 (15) | 0.0022 (15) |
| C122 | 0.033 (3) | 0.032 (3) | 0.036 (3) | 0.002 (2) | 0.009 (2) | 0.005 (2) |
| Cl11 | 0.0466 (9) | 0.0584 (10) | 0.0720 (12) | −0.0008 (7) | 0.0198 (8) | 0.0355 (9) |
| C11A | 0.031 (2) | 0.026 (3) | 0.017 (2) | 0.002 (2) | 0.0016 (19) | −0.0021 (19) |
| C12 | 0.038 (3) | 0.033 (3) | 0.030 (3) | 0.008 (2) | 0.006 (2) | 0.002 (2) |
| C13 | 0.049 (3) | 0.034 (3) | 0.022 (3) | 0.004 (2) | 0.008 (2) | −0.005 (2) |
| C14 | 0.043 (3) | 0.033 (3) | 0.031 (3) | −0.003 (2) | 0.002 (2) | −0.004 (2) |
| C15 | 0.029 (3) | 0.022 (3) | 0.030 (3) | −0.007 (2) | 0.003 (2) | 0.001 (2) |
| C15A | 0.028 (2) | 0.030 (3) | 0.020 (2) | 0.000 (2) | 0.005 (2) | 0.003 (2) |
| N16 | 0.025 (2) | 0.027 (2) | 0.026 (2) | −0.0038 (17) | 0.0055 (17) | −0.0013 (16) |
| C17 | 0.021 (2) | 0.029 (3) | 0.021 (2) | 0.0025 (19) | 0.0000 (19) | 0.0004 (19) |
| C171 | 0.017 (2) | 0.026 (3) | 0.023 (2) | 0.0004 (18) | 0.0008 (19) | 0.0049 (19) |
| C172 | 0.036 (3) | 0.028 (3) | 0.030 (3) | 0.001 (2) | 0.012 (2) | 0.001 (2) |
| C173 | 0.033 (3) | 0.028 (3) | 0.037 (3) | −0.001 (2) | 0.009 (2) | 0.002 (2) |
| C174 | 0.028 (3) | 0.041 (3) | 0.028 (3) | 0.008 (2) | 0.005 (2) | −0.006 (2) |
| C175 | 0.028 (3) | 0.035 (3) | 0.026 (3) | 0.004 (2) | 0.008 (2) | 0.005 (2) |
| C176 | 0.024 (2) | 0.025 (3) | 0.027 (3) | −0.002 (2) | −0.001 (2) | 0.008 (2) |
| C18 | 0.033 (3) | 0.023 (2) | 0.018 (2) | 0.005 (2) | 0.0068 (19) | 0.0015 (19) |
| C19 | 0.030 (2) | 0.023 (3) | 0.019 (2) | −0.0019 (19) | 0.0013 (19) | −0.0044 (18) |
| C191 | 0.023 (2) | 0.027 (3) | 0.023 (2) | 0.0023 (19) | 0.0062 (19) | 0.0017 (19) |
| C192 | 0.026 (2) | 0.033 (3) | 0.019 (2) | 0.003 (2) | 0.007 (2) | 0.000 (2) |
| C193 | 0.032 (3) | 0.037 (3) | 0.039 (3) | −0.003 (2) | 0.013 (2) | 0.004 (2) |
| C194 | 0.032 (3) | 0.042 (3) | 0.033 (3) | 0.003 (2) | 0.014 (2) | 0.006 (2) |
| C195 | 0.049 (3) | 0.043 (3) | 0.022 (3) | 0.000 (3) | 0.010 (2) | 0.003 (2) |
| C196 | 0.031 (3) | 0.031 (3) | 0.028 (3) | −0.004 (2) | 0.005 (2) | −0.003 (2) |
| N21 | 0.0264 (19) | 0.023 (2) | 0.022 (2) | 0.0008 (17) | 0.0067 (16) | −0.0013 (16) |
| C221 | 0.021 (2) | 0.040 (3) | 0.020 (2) | −0.006 (2) | 0.0013 (19) | 0.005 (2) |
| O22 | 0.0238 (18) | 0.040 (2) | 0.0331 (19) | 0.0014 (16) | 0.0104 (15) | 0.0025 (16) |
| C222 | 0.030 (3) | 0.034 (3) | 0.042 (3) | −0.005 (2) | 0.012 (2) | 0.006 (2) |
| Cl21 | 0.0520 (9) | 0.0601 (11) | 0.0664 (11) | −0.0010 (8) | −0.0032 (8) | 0.0370 (9) |
| C21A | 0.027 (2) | 0.030 (3) | 0.024 (2) | −0.002 (2) | 0.014 (2) | −0.0029 (19) |
| C22 | 0.032 (3) | 0.040 (3) | 0.023 (3) | 0.001 (2) | 0.005 (2) | −0.002 (2) |
| C23 | 0.046 (3) | 0.031 (3) | 0.026 (3) | −0.006 (2) | 0.012 (2) | −0.006 (2) |
| C24 | 0.055 (4) | 0.025 (3) | 0.037 (3) | 0.005 (3) | 0.020 (3) | −0.003 (2) |
| C25 | 0.029 (3) | 0.039 (3) | 0.031 (3) | 0.006 (2) | 0.011 (2) | 0.003 (2) |
| C25A | 0.028 (2) | 0.024 (3) | 0.024 (2) | 0.0004 (19) | 0.008 (2) | 0.0009 (19) |
| N26 | 0.023 (2) | 0.033 (3) | 0.026 (2) | 0.0008 (17) | 0.0045 (17) | −0.0014 (17) |
| C27 | 0.020 (2) | 0.024 (3) | 0.024 (2) | −0.0051 (18) | 0.0076 (19) | 0.0010 (18) |
| C271 | 0.015 (2) | 0.038 (3) | 0.024 (2) | −0.0025 (19) | 0.0038 (19) | −0.003 (2) |
| C272 | 0.029 (3) | 0.026 (3) | 0.029 (3) | −0.006 (2) | 0.005 (2) | 0.003 (2) |
| C273 | 0.026 (3) | 0.034 (3) | 0.024 (2) | −0.009 (2) | 0.003 (2) | −0.001 (2) |
| C274 | 0.030 (3) | 0.032 (3) | 0.035 (3) | −0.007 (2) | 0.010 (2) | −0.012 (2) |
| C275 | 0.036 (3) | 0.027 (3) | 0.042 (3) | −0.002 (2) | 0.001 (2) | −0.001 (2) |
| C276 | 0.035 (3) | 0.025 (3) | 0.027 (3) | 0.004 (2) | 0.006 (2) | −0.001 (2) |
| C28 | 0.031 (2) | 0.025 (3) | 0.022 (2) | −0.003 (2) | 0.010 (2) | −0.0017 (19) |
| C29 | 0.028 (2) | 0.028 (3) | 0.022 (2) | −0.001 (2) | 0.007 (2) | 0.0003 (19) |
| C291 | 0.020 (2) | 0.029 (3) | 0.021 (2) | −0.0030 (19) | 0.0062 (18) | −0.0001 (18) |
| C292 | 0.029 (3) | 0.027 (3) | 0.025 (3) | 0.002 (2) | 0.006 (2) | 0.000 (2) |
| C293 | 0.030 (3) | 0.037 (3) | 0.034 (3) | 0.004 (2) | 0.002 (2) | 0.004 (2) |
| C294 | 0.039 (3) | 0.041 (3) | 0.027 (3) | −0.001 (3) | 0.002 (2) | 0.007 (2) |
| C295 | 0.044 (3) | 0.044 (3) | 0.025 (3) | 0.001 (3) | 0.011 (2) | 0.002 (2) |
| C296 | 0.032 (3) | 0.032 (3) | 0.023 (2) | 0.014 (2) | 0.008 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
| N11—C121 | 1.376 (6) | C296—H296 | 0.95 |
| N11—C11A | 1.424 (6) | N31—C321 | 1.3771 |
| N11—C19 | 1.497 (6) | N31—C31A | 1.4228 |
| C121—O12 | 1.217 (6) | N31—C39 | 1.4963 |
| C121—C122 | 1.505 (7) | C321—O32 | 1.2174 |
| C122—Cl11 | 1.779 (6) | C321—C322 | 1.5052 |
| C122—H12A | 0.99 | C322—Cl31 | 1.7805 |
| C122—H12B | 0.99 | C322—H32A | 0.9895 |
| C11A—C12 | 1.381 (7) | C322—H32B | 0.9901 |
| C11A—C15A | 1.393 (7) | C31A—C32 | 1.3813 |
| C12—C13 | 1.391 (8) | C31A—C35A | 1.3922 |
| C12—H12 | 0.95 | C32—C33 | 1.3902 |
| C13—C14 | 1.393 (8) | C32—H32 | 0.9505 |
| C13—H13 | 0.95 | C33—C34 | 1.3912 |
| C14—C15 | 1.376 (8) | C33—H33 | 0.9502 |
| C14—H14 | 0.95 | C34—C35 | 1.3745 |
| C15—C15A | 1.418 (7) | C34—H34 | 0.9493 |
| C15—H15 | 0.95 | C35—C35A | 1.4210 |
| C15A—N16 | 1.423 (6) | C35—H35 | 0.9495 |
| N16—C17 | 1.288 (6) | C35A—N36 | 1.4237 |
| C17—C171 | 1.483 (7) | N36—C37 | 1.2894 |
| C17—C18 | 1.521 (7) | C37—C371 | 1.4817 |
| C171—C176 | 1.384 (7) | C37—C38 | 1.5210 |
| C171—C172 | 1.398 (7) | C371—C376 | 1.3838 |
| C172—C173 | 1.385 (7) | C371—C372 | 1.3990 |
| C172—H172 | 0.95 | C372—C373 | 1.3843 |
| C173—C174 | 1.384 (8) | C372—H372 | 0.9516 |
| C173—H173 | 0.95 | C373—C374 | 1.3823 |
| C174—C175 | 1.381 (7) | C373—H373 | 0.9506 |
| C174—H174 | 0.95 | C374—C375 | 1.3807 |
| C175—C176 | 1.382 (7) | C374—H374 | 0.9503 |
| C175—H175 | 0.95 | C375—C376 | 1.3828 |
| C176—H176 | 0.95 | C375—H375 | 0.9487 |
| C18—C19 | 1.526 (7) | C376—H376 | 0.9499 |
| C18—H18A | 0.99 | C38—C39 | 1.5257 |
| C18—H18B | 0.99 | C38—H38A | 0.9895 |
| C19—C191 | 1.502 (7) | C38—H38B | 0.9899 |
| C19—H19 | 1.00 | C39—C391 | 1.5046 |
| C191—C192 | 1.386 (7) | C39—H39 | 0.9998 |
| C191—C196 | 1.401 (7) | C391—C392 | 1.3858 |
| C192—C193 | 1.391 (7) | C391—C396 | 1.4005 |
| C192—H192 | 0.95 | C392—C393 | 1.3892 |
| C193—C194 | 1.361 (8) | C392—H392 | 0.9495 |
| C193—H193 | 0.95 | C393—C394 | 1.3615 |
| C194—C195 | 1.386 (8) | C393—H393 | 0.9507 |
| C194—H194 | 0.95 | C394—C395 | 1.3872 |
| C195—C196 | 1.381 (8) | C394—H394 | 0.9507 |
| C195—H195 | 0.95 | C395—C396 | 1.3792 |
| C196—H196 | 0.95 | C395—H395 | 0.95 |
| N21—C221 | 1.362 (6) | C396—H396 | 0.9507 |
| N21—C21A | 1.436 (6) | N41—C421 | 1.3638 |
| N21—C29 | 1.486 (6) | N41—C41A | 1.4343 |
| C221—O22 | 1.228 (6) | N41—C49 | 1.4858 |
| C221—C222 | 1.508 (7) | C421—O42 | 1.2275 |
| C222—Cl21 | 1.778 (6) | C421—C422 | 1.5062 |
| C222—H22A | 0.99 | C422—Cl41 | 1.7807 |
| C222—H22B | 0.99 | C422—H42A | 0.9889 |
| C21A—C22 | 1.383 (7) | C422—H42B | 0.9899 |
| C21A—C25A | 1.390 (6) | C41A—C42 | 1.3844 |
| C22—C23 | 1.393 (8) | C41A—C45A | 1.3906 |
| C22—H22 | 0.95 | C42—C43 | 1.3933 |
| C23—C24 | 1.379 (8) | C42—H42 | 0.9483 |
| C23—H23 | 0.95 | C43—C44 | 1.3764 |
| C24—C25 | 1.404 (8) | C43—H43 | 0.9507 |
| C24—H24 | 0.95 | C44—C45 | 1.4035 |
| C25—C25A | 1.389 (7) | C44—H44 | 0.9502 |
| C25—H25 | 0.95 | C45—C45A | 1.3890 |
| C25A—N26 | 1.423 (6) | C45—H45 | 0.9513 |
| N26—C27 | 1.294 (6) | C45A—N46 | 1.4244 |
| C27—C271 | 1.485 (7) | N46—C47 | 1.2950 |
| C27—C28 | 1.501 (7) | C47—C471 | 1.4831 |
| C271—C276 | 1.390 (7) | C47—C48 | 1.4998 |
| C271—C272 | 1.395 (7) | C471—C476 | 1.3909 |
| C272—C273 | 1.389 (7) | C471—C472 | 1.3965 |
| C272—H272 | 0.95 | C472—C473 | 1.3887 |
| C273—C274 | 1.386 (7) | C472—H472 | 0.9501 |
| C273—H273 | 0.95 | C473—C474 | 1.3849 |
| C274—C275 | 1.385 (8) | C473—H473 | 0.9506 |
| C274—H274 | 0.95 | C474—C475 | 1.3847 |
| C274—H472 | 0.8685 | C474—H474 | 0.9498 |
| C275—C276 | 1.382 (7) | C475—C476 | 1.3820 |
| C275—H275 | 0.95 | C475—H475 | 0.95 |
| C275—H472 | 0.7908 | C476—H476 | 0.9501 |
| C276—H276 | 0.95 | C48—C49 | 1.5323 |
| C28—C29 | 1.531 (7) | C48—H48A | 0.9898 |
| C28—H28A | 0.99 | C48—H48B | 0.9901 |
| C28—H28B | 0.99 | C49—C491 | 1.5149 |
| C29—C291 | 1.511 (7) | C49—H49 | 0.9995 |
| C29—H29 | 1.00 | C491—C492 | 1.3751 |
| C291—C292 | 1.377 (7) | C491—C496 | 1.4036 |
| C291—C296 | 1.405 (7) | C492—C493 | 1.3982 |
| C292—C293 | 1.398 (7) | C492—H492 | 0.9514 |
| C292—H292 | 0.95 | C493—C494 | 1.3777 |
| C293—C294 | 1.377 (8) | C493—H493 | 0.9495 |
| C293—H293 | 0.95 | C494—C495 | 1.4019 |
| C294—C295 | 1.404 (8) | C494—H494 | 0.9502 |
| C294—H294 | 0.95 | C495—C496 | 1.3846 |
| C295—C296 | 1.385 (7) | C495—H495 | 0.9511 |
| C295—H295 | 0.95 | C496—H496 | 0.9511 |
| C121—N11—C11A | 123.6 (4) | C321—N31—C31A | 123.6 |
| C121—N11—C19 | 116.6 (4) | C321—N31—C39 | 116.6 |
| C11A—N11—C19 | 119.7 (4) | C31A—N31—C39 | 119.7 |
| O12—C121—N11 | 121.6 (5) | O32—C321—N31 | 121.6 |
| O12—C121—C122 | 120.4 (4) | O32—C321—C322 | 120.4 |
| N11—C121—C122 | 117.9 (4) | N31—C321—C322 | 118.0 |
| C121—C122—Cl11 | 109.1 (4) | C321—C322—Cl31 | 109.0 |
| C121—C122—H12A | 109.9 | C321—C322—H32A | 109.9 |
| Cl11—C122—H12A | 109.9 | Cl31—C322—H32A | 109.9 |
| C121—C122—H12B | 109.9 | C321—C322—H32B | 109.8 |
| Cl11—C122—H12B | 109.9 | Cl31—C322—H32B | 109.9 |
| H12A—C122—H12B | 108.3 | H32A—C322—H32B | 108.3 |
| C12—C11A—C15A | 119.7 (5) | C32—C31A—C35A | 119.6 |
| C12—C11A—N11 | 120.9 (5) | C32—C31A—N31 | 121.0 |
| C15A—C11A—N11 | 119.5 (4) | C35A—C31A—N31 | 119.4 |
| C11A—C12—C13 | 121.4 (6) | C31A—C32—C33 | 121.4 |
| C11A—C12—H12 | 119.3 | C31A—C32—H32 | 119.2 |
| C13—C12—H12 | 119.3 | C33—C32—H32 | 119.3 |
| C12—C13—C14 | 118.6 (5) | C32—C33—C34 | 118.6 |
| C12—C13—H13 | 120.7 | C32—C33—H33 | 120.6 |
| C14—C13—H13 | 120.7 | C34—C33—H33 | 120.8 |
| C15—C14—C13 | 121.5 (5) | C35—C34—C33 | 121.5 |
| C15—C14—H14 | 119.3 | C35—C34—H34 | 119.3 |
| C13—C14—H14 | 119.3 | C33—C34—H34 | 119.2 |
| C14—C15—C15A | 119.2 (5) | C34—C35—C35A | 119.1 |
| C14—C15—H15 | 120.4 | C34—C35—H35 | 120.4 |
| C15A—C15—H15 | 120.4 | C35A—C35—H35 | 120.4 |
| C11A—C15A—C15 | 119.5 (5) | C31A—C35A—C35 | 119.5 |
| C11A—C15A—N16 | 123.0 (4) | C31A—C35A—N36 | 123.1 |
| C15—C15A—N16 | 117.4 (4) | C35—C35A—N36 | 117.3 |
| C17—N16—C15A | 118.0 (4) | C37—N36—C35A | 117.9 |
| N16—C17—C171 | 118.4 (4) | N36—C37—C371 | 118.4 |
| N16—C17—C18 | 121.4 (4) | N36—C37—C38 | 121.4 |
| C171—C17—C18 | 120.1 (4) | C371—C37—C38 | 120.2 |
| C176—C171—C172 | 118.2 (5) | C376—C371—C372 | 118.1 |
| C176—C171—C17 | 119.8 (4) | C376—C371—C37 | 120.0 |
| C172—C171—C17 | 121.9 (4) | C372—C371—C37 | 121.9 |
| C173—C172—C171 | 120.6 (5) | C373—C372—C371 | 120.6 |
| C173—C172—H172 | 119.7 | C373—C372—H372 | 119.7 |
| C171—C172—H172 | 119.7 | C371—C372—H372 | 119.6 |
| C174—C173—C172 | 120.2 (5) | C374—C373—C372 | 120.2 |
| C174—C173—H173 | 119.9 | C374—C373—H373 | 120.0 |
| C172—C173—H173 | 119.9 | C372—C373—H373 | 119.8 |
| C175—C174—C173 | 119.7 (5) | C375—C374—C373 | 119.7 |
| C175—C174—H174 | 120.1 | C375—C374—H374 | 120.1 |
| C173—C174—H174 | 120.1 | C373—C374—H374 | 120.2 |
| C174—C175—C176 | 119.9 (5) | C374—C375—C376 | 119.9 |
| C174—C175—H175 | 120.1 | C374—C375—H375 | 120.1 |
| C176—C175—H175 | 120.1 | C376—C375—H375 | 120.0 |
| C175—C176—C171 | 121.4 (5) | C375—C376—C371 | 121.4 |
| C175—C176—H176 | 119.3 | C375—C376—H376 | 119.3 |
| C171—C176—H176 | 119.3 | C371—C376—H376 | 119.3 |
| C17—C18—C19 | 110.6 (4) | C37—C38—C39 | 110.6 |
| C17—C18—H18A | 109.5 | C37—C38—H38A | 109.5 |
| C19—C18—H18A | 109.5 | C39—C38—H38A | 109.6 |
| C17—C18—H18B | 109.5 | C37—C38—H38B | 109.6 |
| C19—C18—H18B | 109.5 | C39—C38—H38B | 109.4 |
| H18A—C18—H18B | 108.1 | H38A—C38—H38B | 108.1 |
| N11—C19—C191 | 112.8 (4) | N31—C39—C391 | 112.8 |
| N11—C19—C18 | 108.4 (4) | N31—C39—C38 | 108.5 |
| C191—C19—C18 | 114.5 (4) | C391—C39—C38 | 114.4 |
| N11—C19—H19 | 106.9 | N31—C39—H39 | 106.9 |
| C191—C19—H19 | 106.9 | C391—C39—H39 | 106.9 |
| C18—C19—H19 | 106.9 | C38—C39—H39 | 106.8 |
| C192—C191—C196 | 118.9 (5) | C392—C391—C396 | 119.0 |
| C192—C191—C19 | 119.5 (4) | C392—C391—C39 | 119.4 |
| C196—C191—C19 | 121.6 (4) | C396—C391—C39 | 121.6 |
| C191—C192—C193 | 120.2 (4) | C391—C392—C393 | 120.1 |
| C191—C192—H192 | 119.9 | C391—C392—H392 | 119.9 |
| C193—C192—H192 | 119.9 | C393—C392—H392 | 120.0 |
| C194—C193—C192 | 120.8 (5) | C394—C393—C392 | 120.9 |
| C194—C193—H193 | 119.6 | C394—C393—H393 | 119.5 |
| C192—C193—H193 | 119.6 | C392—C393—H393 | 119.6 |
| C193—C194—C195 | 119.6 (5) | C393—C394—C395 | 119.6 |
| C193—C194—H194 | 120.2 | C393—C394—H394 | 120.2 |
| C195—C194—H194 | 120.2 | C395—C394—H394 | 120.2 |
| C196—C195—C194 | 120.6 (5) | C396—C395—C394 | 120.5 |
| C196—C195—H195 | 119.7 | C396—C395—H395 | 119.8 |
| C194—C195—H195 | 119.7 | C394—C395—H395 | 119.7 |
| C195—C196—C191 | 120.0 (5) | C395—C396—C391 | 119.9 |
| C195—C196—H196 | 120.0 | C395—C396—H396 | 120.0 |
| C191—C196—H196 | 120.0 | C391—C396—H396 | 120.1 |
| C221—N21—C21A | 123.3 (4) | C421—N41—C41A | 123.2 |
| C221—N21—C29 | 115.9 (4) | C421—N41—C49 | 115.9 |
| C21A—N21—C29 | 120.8 (4) | C41A—N41—C49 | 120.9 |
| O22—C221—N21 | 122.3 (5) | O42—C421—N41 | 122.2 |
| O22—C221—C222 | 119.0 (4) | O42—C421—C422 | 119.1 |
| N21—C221—C222 | 118.7 (4) | N41—C421—C422 | 118.6 |
| C221—C222—Cl21 | 109.8 (4) | C421—C422—Cl41 | 109.8 |
| C221—C222—H22A | 109.7 | C421—C422—H42A | 109.8 |
| Cl21—C222—H22A | 109.7 | Cl41—C422—H42A | 109.7 |
| C221—C222—H22B | 109.7 | C421—C422—H42B | 109.7 |
| Cl21—C222—H22B | 109.7 | Cl41—C422—H42B | 109.7 |
| H22A—C222—H22B | 108.2 | H42A—C422—H42B | 108.1 |
| C22—C21A—C25A | 120.3 (5) | C42—C41A—C45A | 120.2 |
| C22—C21A—N21 | 120.4 (4) | C42—C41A—N41 | 120.4 |
| C25A—C21A—N21 | 119.3 (4) | C45A—C41A—N41 | 119.3 |
| C21A—C22—C23 | 120.3 (5) | C41A—C42—C43 | 120.3 |
| C21A—C22—H22 | 119.8 | C41A—C42—H42 | 119.9 |
| C23—C22—H22 | 119.8 | C43—C42—H42 | 119.8 |
| C24—C23—C22 | 120.0 (5) | C44—C43—C42 | 120.0 |
| C24—C23—H23 | 120.0 | C44—C43—H43 | 120.1 |
| C22—C23—H23 | 120.0 | C42—C43—H43 | 119.9 |
| C23—C24—C25 | 119.6 (5) | C43—C44—C45 | 119.7 |
| C23—C24—H24 | 120.2 | C43—C44—H44 | 120.2 |
| C25—C24—H24 | 120.2 | C45—C44—H44 | 120.1 |
| C25A—C25—C24 | 120.3 (5) | C45A—C45—C44 | 120.4 |
| C25A—C25—H25 | 119.8 | C45A—C45—H45 | 119.9 |
| C24—C25—H25 | 119.8 | C44—C45—H45 | 119.7 |
| C25—C25A—C21A | 119.4 (4) | C45—C45A—C41A | 119.4 |
| C25—C25A—N26 | 117.4 (4) | C45—C45A—N46 | 117.4 |
| C21A—C25A—N26 | 123.2 (4) | C41A—C45A—N46 | 123.2 |
| C27—N26—C25A | 118.6 (4) | C47—N46—C45A | 118.5 |
| N26—C27—C271 | 117.7 (4) | N46—C47—C471 | 117.6 |
| N26—C27—C28 | 121.1 (4) | N46—C47—C48 | 121.2 |
| C271—C27—C28 | 121.2 (4) | C471—C47—C48 | 121.2 |
| C276—C271—C272 | 118.4 (4) | C476—C471—C472 | 118.3 |
| C276—C271—C27 | 122.3 (4) | C476—C471—C47 | 122.3 |
| C272—C271—C27 | 119.4 (4) | C472—C471—C47 | 119.4 |
| C273—C272—C271 | 120.0 (5) | C473—C472—C471 | 120.0 |
| C273—C272—H272 | 120.0 | C473—C472—H472 | 120.0 |
| C271—C272—H272 | 120.0 | C471—C472—H472 | 120.0 |
| C274—C273—C272 | 120.8 (5) | C474—C473—C472 | 120.9 |
| C274—C273—H273 | 119.6 | C474—C473—H473 | 119.5 |
| C272—C273—H273 | 119.6 | C472—C473—H473 | 119.5 |
| C275—C274—C273 | 119.4 (5) | C475—C474—C473 | 119.4 |
| C275—C274—H274 | 120.3 | C475—C474—H474 | 120.3 |
| C273—C274—H274 | 120.3 | C473—C474—H474 | 120.3 |
| C276—C275—C274 | 119.7 (5) | C476—C475—C474 | 119.7 |
| C276—C275—H275 | 120.1 | C476—C475—H475 | 120.0 |
| C274—C275—H275 | 120.1 | C474—C475—H475 | 120.2 |
| C275—C276—C271 | 121.6 (5) | C475—C476—C471 | 121.6 |
| C275—C276—H276 | 119.2 | C475—C476—H476 | 119.1 |
| C271—C276—H276 | 119.2 | C471—C476—H476 | 119.2 |
| C27—C28—C29 | 110.7 (4) | C47—C48—C49 | 110.6 |
| C27—C28—H28A | 109.5 | C47—C48—H48A | 109.6 |
| C29—C28—H28A | 109.5 | C49—C48—H48A | 109.5 |
| C27—C28—H28B | 109.5 | C47—C48—H48B | 109.5 |
| C29—C28—H28B | 109.5 | C49—C48—H48B | 109.5 |
| H28A—C28—H28B | 108.1 | H48A—C48—H48B | 108.1 |
| N21—C29—C291 | 113.1 (4) | N41—C49—C491 | 113.0 |
| N21—C29—C28 | 108.0 (4) | N41—C49—C48 | 107.9 |
| C291—C29—C28 | 113.6 (4) | C491—C49—C48 | 113.6 |
| N21—C29—H29 | 107.3 | N41—C49—H49 | 107.4 |
| C291—C29—H29 | 107.3 | C491—C49—H49 | 107.3 |
| C28—C29—H29 | 107.3 | C48—C49—H49 | 107.3 |
| C292—C291—C296 | 118.7 (4) | C492—C491—C496 | 118.9 |
| C292—C291—C29 | 119.4 (4) | C492—C491—C49 | 119.2 |
| C296—C291—C29 | 121.9 (4) | C496—C491—C49 | 121.9 |
| C291—C292—C293 | 121.5 (5) | C491—C492—C493 | 121.4 |
| C291—C292—H292 | 119.3 | C491—C492—H492 | 119.3 |
| C293—C292—H292 | 119.3 | C493—C492—H492 | 119.3 |
| C294—C293—C292 | 119.3 (5) | C494—C493—C492 | 119.2 |
| C294—C293—H293 | 120.3 | C494—C493—H493 | 120.4 |
| C292—C293—H293 | 120.3 | C492—C493—H493 | 120.4 |
| C293—C294—C295 | 120.3 (5) | C493—C494—C495 | 120.4 |
| C293—C294—H294 | 119.8 | C493—C494—H494 | 119.7 |
| C295—C294—H294 | 119.8 | C495—C494—H494 | 119.9 |
| C296—C295—C294 | 119.6 (5) | C496—C495—C494 | 119.6 |
| C296—C295—H295 | 120.2 | C496—C495—H495 | 120.2 |
| C294—C295—H295 | 120.2 | C494—C495—H495 | 120.3 |
| C295—C296—C291 | 120.6 (5) | C495—C496—C491 | 120.4 |
| C295—C296—H296 | 119.7 | C495—C496—H496 | 119.7 |
| C291—C296—H296 | 119.7 | C491—C496—H496 | 119.8 |
| C19—N11—C11A—C15A | −65.9 (6) | C31A—N31—C321—O32 | −175.6 |
| N11—C11A—C15A—N16 | −0.6 (7) | C39—N31—C321—O32 | 7.1 |
| C11A—C15A—N16—C17 | 49.5 (6) | C31A—N31—C321—C322 | 5.5 |
| C15A—N16—C17—C18 | 0.7 (6) | C39—N31—C321—C322 | −171.8 |
| N16—C17—C18—C19 | −77.7 (5) | O32—C321—C322—Cl31 | −99.3 |
| C17—C18—C19—N11 | 54.5 (5) | N31—C321—C322—Cl31 | 79.6 |
| C11A—N11—C19—C18 | 29.4 (5) | C321—N31—C31A—C32 | 69.3 |
| N16—C17—C171—C176 | −1.8 (6) | C39—N31—C31A—C32 | −113.5 |
| C18—C17—C171—C176 | 179.6 (4) | C321—N31—C31A—C35A | −111.3 |
| N16—C17—C171—C172 | −178.5 (4) | C39—N31—C31A—C35A | 66.0 |
| C18—C17—C171—C172 | 2.9 (7) | C35A—C31A—C32—C33 | 1.2 |
| C11A—N11—C121—O12 | 175.7 (4) | N31—C31A—C32—C33 | −179.4 |
| C19—N11—C121—O12 | −7.0 (6) | C31A—C32—C33—C34 | −0.2 |
| O12—C121—C122—Cl11 | 99.1 (5) | C32—C33—C34—C35 | 1.1 |
| N11—C121—C122—Cl11 | −79.6 (5) | C33—C34—C35—C35A | −3.0 |
| N11—C19—C191—C192 | −113.5 (5) | C32—C31A—C35A—C35 | −3.0 |
| C18—C19—C191—C192 | 121.9 (5) | N31—C31A—C35A—C35 | 177.5 |
| N11—C19—C191—C196 | 67.8 (6) | C32—C31A—C35A—N36 | −179.9 |
| C18—C19—C191—C196 | −56.9 (6) | N31—C31A—C35A—N36 | 0.6 |
| C11A—N11—C121—C122 | −5.6 (6) | C34—C35—C35A—C31A | 3.9 |
| C19—N11—C121—C122 | 171.7 (4) | C34—C35—C35A—N36 | −179.0 |
| C121—N11—C11A—C12 | −69.3 (6) | C31A—C35A—N36—C37 | −49.4 |
| C19—N11—C11A—C12 | 113.5 (5) | C35—C35A—N36—C37 | 133.6 |
| C121—N11—C11A—C15A | 111.3 (5) | C35A—N36—C37—C371 | 177.9 |
| C15A—C11A—C12—C13 | −1.3 (7) | C35A—N36—C37—C38 | −0.8 |
| N11—C11A—C12—C13 | 179.3 (4) | N36—C37—C371—C376 | 1.6 |
| C11A—C12—C13—C14 | 0.3 (8) | C38—C37—C371—C376 | −179.7 |
| C12—C13—C14—C15 | −1.3 (8) | N36—C37—C371—C372 | 178.5 |
| C13—C14—C15—C15A | 3.2 (8) | C38—C37—C371—C372 | −2.7 |
| C12—C11A—C15A—C15 | 3.2 (7) | C376—C371—C372—C373 | −0.3 |
| N11—C11A—C15A—C15 | −177.4 (4) | C37—C371—C372—C373 | −177.3 |
| C12—C11A—C15A—N16 | −180.0 (4) | C371—C372—C373—C374 | 1.0 |
| C14—C15—C15A—C11A | −4.1 (7) | C372—C373—C374—C375 | −1.5 |
| C14—C15—C15A—N16 | 178.9 (4) | C373—C374—C375—C376 | 1.3 |
| C15—C15A—N16—C17 | −133.6 (5) | C374—C375—C376—C371 | −0.7 |
| C15A—N16—C17—C171 | −177.9 (4) | C372—C371—C376—C375 | 0.2 |
| C176—C171—C172—C173 | 0.4 (7) | C37—C371—C376—C375 | 177.2 |
| C17—C171—C172—C173 | 177.2 (4) | N36—C37—C38—C39 | 77.6 |
| C171—C172—C173—C174 | −1.0 (8) | C371—C37—C38—C39 | −101.1 |
| C172—C173—C174—C175 | 1.4 (7) | C321—N31—C39—C391 | −84.1 |
| C173—C174—C175—C176 | −1.4 (7) | C31A—N31—C39—C391 | 98.5 |
| C174—C175—C176—C171 | 0.9 (7) | C321—N31—C39—C38 | 148.0 |
| C172—C171—C176—C175 | −0.4 (7) | C31A—N31—C39—C38 | −29.4 |
| C17—C171—C176—C175 | −177.2 (4) | C37—C38—C39—N31 | −54.5 |
| C171—C17—C18—C19 | 100.9 (5) | C37—C38—C39—C391 | 178.6 |
| C121—N11—C19—C191 | 84.1 (5) | N31—C39—C391—C392 | 113.5 |
| C11A—N11—C19—C191 | −98.5 (5) | C38—C39—C391—C392 | −121.8 |
| C121—N11—C19—C18 | −148.0 (4) | N31—C39—C391—C396 | −67.8 |
| C17—C18—C19—C191 | −178.5 (4) | C38—C39—C391—C396 | 56.9 |
| C196—C191—C192—C193 | 0.4 (7) | C396—C391—C392—C393 | −0.5 |
| C19—C191—C192—C193 | −178.4 (5) | C39—C391—C392—C393 | 178.3 |
| C191—C192—C193—C194 | −0.9 (8) | C391—C392—C393—C394 | 1.1 |
| C192—C193—C194—C195 | 1.0 (8) | C392—C393—C394—C395 | −1.1 |
| C193—C194—C195—C196 | −0.6 (9) | C393—C394—C395—C396 | 0.6 |
| C194—C195—C196—C191 | 0.2 (8) | C394—C395—C396—C391 | −0.1 |
| C192—C191—C196—C195 | −0.1 (8) | C392—C391—C396—C395 | 0.0 |
| C19—C191—C196—C195 | 178.7 (5) | C39—C391—C396—C395 | −178.7 |
| C29—N21—C21A—C25A | 65.1 (6) | C41A—N41—C421—O42 | 175.4 |
| N21—C21A—C25A—N26 | 0.6 (7) | C49—N41—C421—O42 | −6.4 |
| C21A—C25A—N26—C27 | −47.2 (7) | C41A—N41—C421—C422 | −6.9 |
| C25A—N26—C27—C28 | −3.4 (7) | C49—N41—C421—C422 | 171.3 |
| N26—C27—C28—C29 | 79.6 (6) | O42—C421—C422—Cl41 | 98.9 |
| C21A—N21—C29—C28 | −29.2 (5) | N41—C421—C422—Cl41 | −78.8 |
| C27—C28—C29—N21 | −54.9 (5) | C421—N41—C41A—C42 | −68.5 |
| C21A—N21—C221—O22 | −175.4 (4) | C49—N41—C41A—C42 | 113.4 |
| C29—N21—C221—O22 | 6.4 (6) | C421—N41—C41A—C45A | 113.1 |
| O22—C221—C222—Cl21 | −99.0 (5) | C49—N41—C41A—C45A | −64.9 |
| N21—C221—C222—Cl21 | 78.7 (5) | C45A—C41A—C42—C43 | −2.5 |
| N26—C27—C271—C276 | 175.2 (5) | N41—C41A—C42—C43 | 179.2 |
| C28—C27—C271—C276 | −4.2 (7) | C41A—C42—C43—C44 | 1.5 |
| N26—C27—C271—C272 | −4.3 (7) | C42—C43—C44—C45 | −0.8 |
| C28—C27—C271—C272 | 176.3 (4) | C43—C44—C45—C45A | 1.2 |
| N21—C29—C291—C292 | 114.4 (5) | C44—C45—C45A—C41A | −2.1 |
| C28—C29—C291—C292 | −122.1 (5) | C44—C45—C45A—N46 | 179.7 |
| N21—C29—C291—C296 | −66.2 (6) | C42—C41A—C45A—C45 | 2.8 |
| C28—C29—C291—C296 | 57.4 (6) | N41—C41A—C45A—C45 | −178.9 |
| C21A—N21—C221—C222 | 6.9 (6) | C42—C41A—C45A—N46 | −179.1 |
| C29—N21—C221—C222 | −171.2 (4) | N41—C41A—C45A—N46 | −0.8 |
| C221—N21—C21A—C22 | 68.5 (6) | C45—C45A—N46—C47 | −134.6 |
| C29—N21—C21A—C22 | −113.4 (5) | C41A—C45A—N46—C47 | 47.2 |
| C221—N21—C21A—C25A | −113.0 (5) | C45A—N46—C47—C471 | −177.2 |
| C25A—C21A—C22—C23 | 2.4 (8) | C45A—N46—C47—C48 | 3.6 |
| N21—C21A—C22—C23 | −179.1 (5) | N46—C47—C471—C476 | −175.0 |
| C21A—C22—C23—C24 | −1.6 (8) | C48—C47—C471—C476 | 4.3 |
| C22—C23—C24—C25 | 1.0 (8) | N46—C47—C471—C472 | 4.3 |
| C23—C24—C25—C25A | −1.2 (8) | C48—C47—C471—C472 | −176.4 |
| C24—C25—C25A—C21A | 2.0 (8) | C476—C471—C472—C473 | 2.5 |
| C24—C25—C25A—N26 | −179.6 (5) | C47—C471—C472—C473 | −176.9 |
| C22—C21A—C25A—C25 | −2.6 (7) | C471—C472—C473—C474 | −1.0 |
| N21—C21A—C25A—C25 | 178.9 (4) | C472—C473—C474—C475 | −1.2 |
| C22—C21A—C25A—N26 | 179.1 (5) | C473—C474—C475—C476 | 2.0 |
| C25—C25A—N26—C27 | 134.4 (5) | C474—C475—C476—C471 | −0.5 |
| C25A—N26—C27—C271 | 177.2 (4) | C472—C471—C476—C475 | −1.7 |
| C276—C271—C272—C273 | −2.5 (7) | C47—C471—C476—C475 | 177.6 |
| C27—C271—C272—C273 | 176.9 (4) | N46—C47—C48—C49 | −79.8 |
| C271—C272—C273—C274 | 1.0 (8) | C471—C47—C48—C49 | 101.0 |
| C272—C273—C274—C275 | 1.4 (8) | C421—N41—C49—C491 | 84.5 |
| C273—C274—C275—C276 | −2.1 (8) | C41A—N41—C49—C491 | −97.3 |
| C274—C275—C276—C271 | 0.5 (8) | C421—N41—C49—C48 | −149.0 |
| C272—C271—C276—C275 | 1.8 (8) | C41A—N41—C49—C48 | 29.2 |
| C27—C271—C276—C275 | −177.7 (5) | C47—C48—C49—N41 | 55.0 |
| C271—C27—C28—C29 | −101.0 (5) | C47—C48—C49—C491 | −178.9 |
| C221—N21—C29—C291 | −84.4 (5) | N41—C49—C491—C492 | −114.6 |
| C21A—N21—C29—C291 | 97.4 (5) | C48—C49—C491—C492 | 122.0 |
| C221—N21—C29—C28 | 149.0 (4) | N41—C49—C491—C496 | 66.2 |
| C27—C28—C29—C291 | 178.8 (4) | C48—C49—C491—C496 | −57.2 |
| C296—C291—C292—C293 | −1.7 (8) | C496—C491—C492—C493 | 1.4 |
| C29—C291—C292—C293 | 177.8 (5) | C49—C491—C492—C493 | −177.8 |
| C291—C292—C293—C294 | 2.4 (8) | C491—C492—C493—C494 | −2.2 |
| C292—C293—C294—C295 | −1.8 (8) | C492—C493—C494—C495 | 1.7 |
| C293—C294—C295—C296 | 0.6 (9) | C493—C494—C495—C496 | −0.4 |
| C294—C295—C296—C291 | 0.1 (8) | C494—C495—C496—C491 | −0.4 |
| C292—C291—C296—C295 | 0.4 (8) | C492—C491—C496—C495 | −0.1 |
| C29—C291—C296—C295 | −179.0 (5) | C49—C491—C496—C495 | 179.1 |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C122—H12A···O22 | 0.99 | 2.23 | 3.110 (19) | 148 |
| C222—H22B···O12i | 0.99 | 2.26 | 3.144 (19) | 148 |
| C194—H194···O12ii | 0.95 | 2.57 | 3.297 (16) | 133 |
| C294—H294···O22iii | 0.95 | 2.58 | 3.285 (16) | 132 |
| Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2; (iii) x, −y+1, z−1/2. |
Experimental details
| Crystal data | |
| Chemical formula | C23H19ClN2O |
| Mr | 374.85 |
| Crystal system, space group | Monoclinic, Cc |
| Temperature (K) | 120 |
| a, b, c (Å) | 31.7081 (8), 7.8174 (2), 15.4208 (5) |
| β (°) | 104.344 (1) |
| V (Å3) | 3703.27 (18) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.22 |
| Crystal size (mm) | 0.36 × 0.12 × 0.08 |
| Data collection | |
| Diffractometer | Nonius KappaCCD diffractometer |
| Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
| Tmin, Tmax | 0.925, 0.983 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 17924, 7396, 5168 |
| Rint | 0.095 |
| (sin θ/λ)max (Å−1) | 0.645 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.201, 1.04 |
| No. of reflections | 7396 |
| No. of parameters | 488 |
| No. of restraints | 2 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.40, −0.40 |
| Absolute structure | Flack (1983), 4142 Friedel pairs |
| Absolute structure parameter | 0.09 (10) |
Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2003), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
Selected geometric parameters (Å, º) top
| N11—C11A | 1.424 (6) | N21—C21A | 1.436 (6) |
| N11—C19 | 1.497 (6) | N21—C29 | 1.486 (6) |
| C11A—C15A | 1.393 (7) | C21A—C25A | 1.390 (6) |
| C15A—N16 | 1.423 (6) | C25A—N26 | 1.423 (6) |
| N16—C17 | 1.288 (6) | N26—C27 | 1.294 (6) |
| C17—C18 | 1.521 (7) | C27—C28 | 1.501 (7) |
| C18—C19 | 1.526 (7) | C28—C29 | 1.531 (7) |
| C11A—N11—C19 | 119.7 (4) | C21A—N21—C29 | 120.8 (4) |
| C15A—C11A—N11 | 119.5 (4) | C25A—C21A—N21 | 119.3 (4) |
| C11A—C15A—N16 | 123.0 (4) | C21A—C25A—N26 | 123.2 (4) |
| C17—N16—C15A | 118.0 (4) | C27—N26—C25A | 118.6 (4) |
| N16—C17—C18 | 121.4 (4) | N26—C27—C28 | 121.1 (4) |
| C17—C18—C19 | 110.6 (4) | C27—C28—C29 | 110.7 (4) |
| N11—C19—C18 | 108.4 (4) | N21—C29—C28 | 108.0 (4) |
| C19—N11—C11A—C15A | −65.9 (6) | C29—N21—C21A—C25A | 65.1 (6) |
| N11—C11A—C15A—N16 | −0.6 (7) | N21—C21A—C25A—N26 | 0.6 (7) |
| C11A—C15A—N16—C17 | 49.5 (6) | C21A—C25A—N26—C27 | −47.2 (7) |
| C15A—N16—C17—C18 | 0.7 (6) | C25A—N26—C27—C28 | −3.4 (7) |
| N16—C17—C18—C19 | −77.7 (5) | N26—C27—C28—C29 | 79.6 (6) |
| C17—C18—C19—N11 | 54.5 (5) | C21A—N21—C29—C28 | −29.2 (5) |
| C11A—N11—C19—C18 | 29.4 (5) | C27—C28—C29—N21 | −54.9 (5) |
| N16—C17—C171—C176 | −1.8 (6) | C21A—N21—C221—O22 | −175.4 (4) |
| C18—C17—C171—C176 | 179.6 (4) | C29—N21—C221—O22 | 6.4 (6) |
| N16—C17—C171—C172 | −178.5 (4) | O22—C221—C222—Cl21 | −99.0 (5) |
| C18—C17—C171—C172 | 2.9 (7) | N21—C221—C222—Cl21 | 78.7 (5) |
| C11A—N11—C121—O12 | 175.7 (4) | N26—C27—C271—C276 | 175.2 (5) |
| C19—N11—C121—O12 | −7.0 (6) | C28—C27—C271—C276 | −4.2 (7) |
| O12—C121—C122—Cl11 | 99.1 (5) | N26—C27—C271—C272 | −4.3 (7) |
| N11—C121—C122—Cl11 | −79.6 (5) | C28—C27—C271—C272 | 176.3 (4) |
| N11—C19—C191—C192 | −113.5 (5) | N21—C29—C291—C292 | 114.4 (5) |
| C18—C19—C191—C192 | 121.9 (5) | C28—C29—C291—C292 | −122.1 (5) |
| N11—C19—C191—C196 | 67.8 (6) | N21—C29—C291—C296 | −66.2 (6) |
| C18—C19—C191—C196 | −56.9 (6) | C28—C29—C291—C296 | 57.4 (6) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C122—H12A···O22 | 0.99 | 2.23 | 3.110 (19) | 148 |
| C222—H22B···O12i | 0.99 | 2.26 | 3.144 (19) | 148 |
| C194—H194···O12ii | 0.95 | 2.57 | 3.297 (16) | 133 |
| C294—H294···O22iii | 0.95 | 2.58 | 3.285 (16) | 132 |
| Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z−1/2; (iii) x, −y+1, z−1/2. |
Benzodiazepines are an important class of psychotherapeutic compounds. Here we describe the racemic mixture resulting from a N-chloroacetylation of the corresponding racemate 2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine (Insuasty et al., 1992).
The structure, (I), is disordered with the minor component consisting of two molecules whose coordinates are related to those of the major component by the transformation (x, −y, z). As can be seen in Table 1, the bonds and angles of the two molecules in the asymmetric unit show no differences at a significance level of 3σ. There are some slight variations in the magnitudes of the torsion angles of the diazepine rings involving atoms Nn6, Cn7 and Cn8 (n = 1 or 2). The two molecules of the asymmetric unit were chosen such that they were linked by the weak C122—H12A···O22 hydrogen bond, for details see Table 2. A similar bond involving C222—H22a···O21(x, −1 + y, z) links the molecules by a C22(8) chain (Bernstein et al., 1995) which runs parallel to the b axis (Fig. 2).
The molecules of the R conformer are linked together to form a C9 chain by the weak hydrogen-bond C194—H194···O12(x, 2 − y, z − 0.5) (Fig. 3). The molecules of the S conformer are linked by an identical chain formed by the weak hydrogen-bond C294—H294···O22(x, 1 − y, z − 0.5) (Table 2). These chains run parallel to the c axis.