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
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (Please check) = 0.000 Å
- Disorder in solvent or counterion
- R factor = 0.068
- wR factor = 0.201
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) >H(293)
Author response: ...When the major and minor components are run separately in PLATON or CHECKCIF there is no problem with the connectivity nor does SHELXL indicate any problem nor should it since h293 is an AFIX 43 atom. There is no connectivity problem. Also the large number of Alert-Cs arise because the minor component is in a fixed position. |
PLAT_305 Alert A Isolated Hydrogen Atom (Outside Bond Range ??) <H(493)
Author response: ...When the major and minor components are run separately in PLATON or CHECKCIF there is no problem with the connectivity nor does SHELXL indicate any problem nor should it since h293 is an AFIX 43 atom. There is no connectivity problem. Also the large number of Alert-Cs arise because the minor component is in a fixed position. |
Alert Level C:
PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . N31 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C321 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . O32 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C322 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . CL31 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C31A PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C32 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C33 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C34 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C35 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C35A PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . N36 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C37 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C371 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C372 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C373 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C374 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C375 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C376 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C38 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C39 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C391 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C392 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C393 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C394 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C395 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C396 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . N41 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C421 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . O42 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C422 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . CL41 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C41A PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C42 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C43 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C44 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C45 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C45A PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . N46 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C47 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C471 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C472 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C473 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C474 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C475 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C476 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C48 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C49 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C491 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C492 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C493 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C494 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C495 PLAT_161 Alert C Missing or Zero su (esd) on x-coordinate for . C496 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . N31 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C321 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . O32 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C322 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . CL31 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C31A PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C32 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C33 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C34 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C35 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C35A PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . N36 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C37 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C371 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C372 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C373 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C374 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C375 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C376 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C38 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C39 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C391 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C392 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C393 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C394 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C395 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C396 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . N41 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C421 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . O42 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C422 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . CL41 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C41A PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C42 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C43 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C44 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C45 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C45A PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . N46 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C47 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C471 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C472 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C473 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C474 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C475 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C476 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C48 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C49 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C491 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C492 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C493 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C494 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C495 PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . C496 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . N31 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C321 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . O32 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C322 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . CL31 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C31A PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C32 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C33 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C34 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C35 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C35A PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . N36 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C37 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C371 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C372 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C373 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C374 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C375 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C376 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C38 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C39 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C391 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C392 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C393 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C394 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C395 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C396 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . N41 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C421 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . O42 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C422 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . CL41 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C41A PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C42 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C43 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C44 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C45 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C45A PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . N46 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C47 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C471 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C472 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C473 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C474 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C475 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C476 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C48 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C49 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C491 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C492 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C493 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C494 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C495 PLAT_163 Alert C Missing or Zero su (esd) on z-coordinate for . C496 PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.27 From the CIF: _reflns_number_total 7396 Count of symmetry unique reflns 4147 Completeness (_total/calc) 178.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3249 Fraction of Friedel pairs measured 0.783 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
163 Alert Level C = Please check
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%.
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%.
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).
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 |
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 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) |
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)° |
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 |
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 |
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. |
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 |
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) |
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 |
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).
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) |
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. |
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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.