The asymmetric unit of the title compound, C
24H
23NO, contains two crystallographically independent molecules (
A and
B). In both molecules, the piperidine rings adopt a chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The dihedral angle between the phenyl rings is 60.80 (10)° in molecule
A and 68.43 (9)° in molecule
B. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10)° with the phenyl rings in molecule
A, and dihedral angles of 81.38 (11) and 30.19 (11)° in molecule
B. In the crystal, the two molecules are linked by N—H

O hydrogen bonds, forming –
A–
B–
A–
B– chains along [100]. In addition, five C—H

π interactions are also present, linking the chains to form a three-dimensional structure.
Supporting information
CCDC reference: 1451096
Key indicators
- Single-crystal X-ray study
- T = 178 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.066
- wR factor = 0.150
- Data-to-parameter ratio = 22.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 9.085 Check
Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do !
PLAT793_ALERT_4_G The Model has Chirality at C2A (Centro SPGR) S Verify
PLAT793_ALERT_4_G The Model has Chirality at C2B (Centro SPGR) S Verify
PLAT793_ALERT_4_G The Model has Chirality at C3A (Centro SPGR) R Verify
PLAT793_ALERT_4_G The Model has Chirality at C3B (Centro SPGR) R Verify
PLAT793_ALERT_4_G The Model has Chirality at C6A (Centro SPGR) R Verify
PLAT793_ALERT_4_G The Model has Chirality at C6B (Centro SPGR) R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 46 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
9 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and
publCIF (Westrip, 2010).
t-3-Benzyl-
r-2,
c-6-diphenylpiperidin-4-one
top
Crystal data top
C24H23NO | F(000) = 1456 |
Mr = 341.43 | Dx = 1.211 Mg m−3 |
Monoclinic, P21/n | Melting point: 471 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8918 (5) Å | Cell parameters from 7035 reflections |
b = 30.6042 (12) Å | θ = 2.6–22.8° |
c = 12.3878 (6) Å | µ = 0.07 mm−1 |
β = 92.426 (2)° | T = 178 K |
V = 3746.8 (3) Å3 | Plate, colourless |
Z = 8 | 0.40 × 0.36 × 0.16 mm |
Data collection top
Bruker Kappa APEXIII CCD area-detector diffractometer | 10617 independent reflections |
Radiation source: fine-focus sealed tube | 6350 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.078 |
φ and ω scans | θmax = 29.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −13→13 |
Tmin = 0.81, Tmax = 0.99 | k = −42→42 |
58653 measured reflections | l = −14→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: mixed |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0506P)2 + 1.0513P] where P = (Fo2 + 2Fc2)/3 |
10617 reflections | (Δ/σ)max = 0.001 |
477 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O4A | 0.66207 (13) | 0.14287 (4) | 0.97486 (11) | 0.0395 (5) | |
N1A | 0.29441 (15) | 0.17242 (5) | 0.87397 (13) | 0.0294 (5) | |
C2A | 0.33073 (17) | 0.12682 (5) | 0.89839 (14) | 0.0255 (5) | |
C3A | 0.42875 (17) | 0.12561 (5) | 0.99936 (14) | 0.0258 (5) | |
C4A | 0.54612 (18) | 0.15567 (6) | 0.97724 (14) | 0.0287 (5) | |
O4B | 0.64521 (13) | 0.35463 (4) | 0.14639 (11) | 0.0398 (4) | |
C5A | 0.50630 (18) | 0.20176 (6) | 0.94862 (15) | 0.0310 (6) | |
C6A | 0.40932 (18) | 0.20027 (5) | 0.84847 (14) | 0.0281 (5) | |
C13A | 0.4738 (2) | 0.07909 (6) | 1.02805 (14) | 0.0316 (6) | |
C21A | 0.20186 (17) | 0.10166 (5) | 0.91607 (13) | 0.0256 (5) | |
C22A | 0.10267 (19) | 0.11842 (6) | 0.98114 (15) | 0.0327 (6) | |
C23A | −0.0152 (2) | 0.09519 (7) | 0.99688 (16) | 0.0376 (6) | |
C24A | −0.0346 (2) | 0.05489 (7) | 0.94932 (16) | 0.0385 (7) | |
C25A | 0.0624 (2) | 0.03799 (6) | 0.88431 (16) | 0.0371 (6) | |
C26A | 0.17976 (19) | 0.06132 (6) | 0.86759 (15) | 0.0314 (6) | |
C31A | 0.53595 (17) | 0.07396 (5) | 1.14082 (14) | 0.0260 (5) | |
C32A | 0.4699 (2) | 0.08900 (6) | 1.22942 (16) | 0.0368 (6) | |
C33A | 0.5230 (2) | 0.08269 (7) | 1.33323 (17) | 0.0462 (7) | |
C34A | 0.6440 (2) | 0.06114 (7) | 1.35011 (17) | 0.0440 (7) | |
C35A | 0.7111 (2) | 0.04598 (6) | 1.26319 (17) | 0.0393 (6) | |
C36A | 0.65797 (18) | 0.05231 (5) | 1.15920 (15) | 0.0315 (6) | |
C61A | 0.35679 (18) | 0.24486 (5) | 0.81445 (15) | 0.0292 (6) | |
C62A | 0.3975 (2) | 0.26388 (6) | 0.72053 (17) | 0.0437 (7) | |
C63A | 0.3443 (3) | 0.30352 (7) | 0.68587 (19) | 0.0560 (9) | |
C64A | 0.2511 (2) | 0.32475 (7) | 0.74529 (19) | 0.0490 (8) | |
C65A | 0.2101 (2) | 0.30642 (7) | 0.83958 (19) | 0.0484 (8) | |
C66A | 0.2627 (2) | 0.26665 (6) | 0.87408 (18) | 0.0425 (7) | |
N1B | 0.28747 (15) | 0.32434 (5) | 0.24447 (13) | 0.0290 (5) | |
C2B | 0.31937 (17) | 0.36986 (5) | 0.21806 (14) | 0.0260 (5) | |
C3B | 0.40928 (17) | 0.37099 (5) | 0.11867 (14) | 0.0254 (5) | |
C4B | 0.52943 (18) | 0.34139 (6) | 0.14279 (14) | 0.0282 (5) | |
C5B | 0.49399 (19) | 0.29549 (6) | 0.17362 (15) | 0.0323 (6) | |
C6B | 0.40709 (17) | 0.29780 (5) | 0.27294 (14) | 0.0280 (5) | |
C13B | 0.45080 (19) | 0.41762 (6) | 0.09216 (15) | 0.0311 (6) | |
C21B | 0.18873 (17) | 0.39485 (5) | 0.19832 (13) | 0.0258 (5) | |
C22B | 0.08347 (18) | 0.37718 (6) | 0.13450 (14) | 0.0308 (6) | |
C23B | −0.03523 (19) | 0.40058 (6) | 0.11528 (15) | 0.0347 (6) | |
C24B | −0.0486 (2) | 0.44195 (6) | 0.15741 (16) | 0.0370 (6) | |
C25B | 0.0544 (2) | 0.45969 (6) | 0.22133 (16) | 0.0378 (6) | |
C26B | 0.17202 (19) | 0.43595 (6) | 0.24253 (15) | 0.0323 (6) | |
C31B | 0.52074 (18) | 0.42469 (6) | −0.01175 (15) | 0.0306 (6) | |
C32B | 0.4822 (2) | 0.40348 (7) | −0.10618 (16) | 0.0419 (7) | |
C33B | 0.5413 (3) | 0.41335 (9) | −0.20217 (18) | 0.0574 (9) | |
C34B | 0.6411 (3) | 0.44425 (10) | −0.2052 (3) | 0.0717 (11) | |
C35B | 0.6830 (3) | 0.46507 (9) | −0.1112 (3) | 0.0744 (13) | |
C36B | 0.6227 (2) | 0.45573 (7) | −0.0158 (2) | 0.0507 (8) | |
C61B | 0.36041 (18) | 0.25385 (5) | 0.31273 (15) | 0.0291 (5) | |
C62B | 0.3830 (2) | 0.24185 (6) | 0.41921 (16) | 0.0392 (7) | |
C63B | 0.3325 (2) | 0.20300 (7) | 0.45824 (18) | 0.0478 (7) | |
C64B | 0.2605 (2) | 0.17535 (7) | 0.39071 (18) | 0.0444 (7) | |
C65B | 0.2378 (2) | 0.18668 (7) | 0.28414 (19) | 0.0486 (8) | |
C66B | 0.2869 (2) | 0.22564 (6) | 0.24535 (17) | 0.0424 (7) | |
H1A | 0.2395 (19) | 0.1715 (6) | 0.8167 (16) | 0.032 (5)* | |
H2A | 0.37692 | 0.11399 | 0.83550 | 0.0306* | |
H3A | 0.38018 | 0.13776 | 1.06185 | 0.0310* | |
H5A | 0.58761 | 0.21914 | 0.93306 | 0.0372* | |
H5B | 0.46113 | 0.21559 | 1.00971 | 0.0372* | |
H6A | 0.45740 | 0.18695 | 0.78715 | 0.0338* | |
H13A | 0.39449 | 0.05946 | 1.02003 | 0.0379* | |
H13B | 0.54056 | 0.06950 | 0.97562 | 0.0379* | |
H22A | 0.11594 | 0.14603 | 1.01501 | 0.0392* | |
H23A | −0.08264 | 0.10710 | 1.04059 | 0.0451* | |
H24A | −0.11467 | 0.03876 | 0.96126 | 0.0461* | |
H25A | 0.04871 | 0.01030 | 0.85092 | 0.0445* | |
H26A | 0.24584 | 0.04953 | 0.82236 | 0.0376* | |
H32A | 0.38624 | 0.10399 | 1.21885 | 0.0441* | |
H33A | 0.47574 | 0.09327 | 1.39309 | 0.0554* | |
H34A | 0.68070 | 0.05681 | 1.42141 | 0.0528* | |
H35A | 0.79466 | 0.03102 | 1.27435 | 0.0471* | |
H36A | 0.70571 | 0.04169 | 1.09964 | 0.0378* | |
H62A | 0.46288 | 0.24961 | 0.67898 | 0.0523* | |
H63A | 0.37263 | 0.31607 | 0.62044 | 0.0672* | |
H64A | 0.21491 | 0.35202 | 0.72143 | 0.0588* | |
H65A | 0.14561 | 0.32105 | 0.88125 | 0.0580* | |
H66A | 0.23387 | 0.25417 | 0.93945 | 0.0510* | |
H1B | 0.235 (2) | 0.3253 (7) | 0.3023 (18) | 0.050 (7)* | |
H2B | 0.37069 | 0.38323 | 0.28103 | 0.0312* | |
H3B | 0.35600 | 0.35885 | 0.05514 | 0.0305* | |
H5C | 0.44317 | 0.28096 | 0.11314 | 0.0387* | |
H5D | 0.57736 | 0.27849 | 0.19060 | 0.0387* | |
H6B | 0.46029 | 0.31264 | 0.33280 | 0.0336* | |
H13C | 0.51134 | 0.42836 | 0.15210 | 0.0373* | |
H13D | 0.36851 | 0.43606 | 0.09058 | 0.0373* | |
H22B | 0.09285 | 0.34893 | 0.10390 | 0.0369* | |
H23B | −0.10755 | 0.38805 | 0.07293 | 0.0417* | |
H24B | −0.12897 | 0.45821 | 0.14230 | 0.0444* | |
H25B | 0.04501 | 0.48812 | 0.25088 | 0.0453* | |
H26B | 0.24209 | 0.44807 | 0.28802 | 0.0387* | |
H32B | 0.41384 | 0.38169 | −0.10523 | 0.0503* | |
H33B | 0.51247 | 0.39860 | −0.26658 | 0.0688* | |
H34B | 0.68106 | 0.45124 | −0.27144 | 0.0860* | |
H35B | 0.75387 | 0.48600 | −0.11212 | 0.0891* | |
H36B | 0.65135 | 0.47074 | 0.04831 | 0.0608* | |
H62B | 0.43397 | 0.26056 | 0.46664 | 0.0470* | |
H63B | 0.34799 | 0.19550 | 0.53215 | 0.0573* | |
H64B | 0.22648 | 0.14857 | 0.41727 | 0.0533* | |
H65B | 0.18806 | 0.16759 | 0.23683 | 0.0583* | |
H66B | 0.27005 | 0.23318 | 0.17162 | 0.0509* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O4A | 0.0305 (7) | 0.0438 (8) | 0.0443 (9) | 0.0043 (6) | 0.0016 (6) | 0.0055 (6) |
N1A | 0.0308 (8) | 0.0251 (7) | 0.0316 (9) | −0.0028 (6) | −0.0066 (7) | 0.0049 (6) |
C2A | 0.0304 (9) | 0.0229 (8) | 0.0231 (9) | −0.0009 (7) | 0.0001 (7) | −0.0003 (7) |
C3A | 0.0297 (9) | 0.0248 (8) | 0.0229 (9) | 0.0011 (7) | 0.0003 (7) | −0.0011 (7) |
C4A | 0.0313 (10) | 0.0341 (9) | 0.0204 (9) | −0.0003 (8) | −0.0031 (7) | −0.0024 (7) |
O4B | 0.0283 (7) | 0.0468 (8) | 0.0442 (8) | −0.0015 (6) | 0.0012 (6) | 0.0078 (6) |
C5A | 0.0312 (10) | 0.0277 (9) | 0.0337 (10) | −0.0050 (7) | −0.0020 (8) | −0.0011 (8) |
C6A | 0.0315 (10) | 0.0244 (8) | 0.0286 (10) | −0.0020 (7) | 0.0021 (8) | 0.0002 (7) |
C13A | 0.0411 (11) | 0.0263 (9) | 0.0272 (10) | 0.0031 (8) | −0.0014 (8) | −0.0001 (7) |
C21A | 0.0304 (9) | 0.0258 (8) | 0.0202 (9) | 0.0003 (7) | −0.0018 (7) | 0.0053 (7) |
C22A | 0.0362 (10) | 0.0321 (10) | 0.0297 (10) | 0.0016 (8) | 0.0008 (8) | −0.0009 (8) |
C23A | 0.0330 (10) | 0.0501 (12) | 0.0300 (10) | 0.0028 (9) | 0.0052 (8) | 0.0054 (9) |
C24A | 0.0346 (11) | 0.0454 (12) | 0.0351 (11) | −0.0084 (9) | −0.0013 (9) | 0.0143 (9) |
C25A | 0.0449 (12) | 0.0290 (9) | 0.0371 (11) | −0.0091 (9) | −0.0010 (9) | 0.0027 (8) |
C26A | 0.0367 (10) | 0.0264 (9) | 0.0312 (10) | −0.0031 (8) | 0.0036 (8) | 0.0009 (7) |
C31A | 0.0293 (9) | 0.0212 (8) | 0.0276 (10) | −0.0026 (7) | 0.0016 (8) | 0.0032 (7) |
C32A | 0.0347 (10) | 0.0420 (11) | 0.0338 (11) | 0.0067 (9) | 0.0043 (9) | 0.0042 (9) |
C33A | 0.0590 (14) | 0.0516 (13) | 0.0283 (11) | 0.0007 (11) | 0.0068 (10) | 0.0012 (9) |
C34A | 0.0560 (14) | 0.0418 (11) | 0.0329 (12) | −0.0073 (10) | −0.0124 (10) | 0.0072 (9) |
C35A | 0.0340 (10) | 0.0316 (10) | 0.0511 (13) | −0.0010 (8) | −0.0117 (10) | 0.0077 (9) |
C36A | 0.0315 (10) | 0.0249 (9) | 0.0383 (11) | −0.0001 (7) | 0.0041 (8) | 0.0017 (8) |
C61A | 0.0331 (10) | 0.0243 (9) | 0.0299 (10) | −0.0047 (7) | −0.0023 (8) | −0.0008 (7) |
C62A | 0.0594 (14) | 0.0316 (10) | 0.0407 (12) | 0.0011 (10) | 0.0106 (10) | 0.0053 (9) |
C63A | 0.0872 (19) | 0.0361 (12) | 0.0454 (14) | 0.0026 (12) | 0.0110 (13) | 0.0135 (10) |
C64A | 0.0661 (15) | 0.0275 (10) | 0.0525 (14) | 0.0041 (10) | −0.0089 (12) | 0.0060 (10) |
C65A | 0.0529 (14) | 0.0333 (11) | 0.0591 (15) | 0.0089 (10) | 0.0041 (11) | −0.0025 (10) |
C66A | 0.0503 (13) | 0.0331 (10) | 0.0447 (12) | 0.0049 (9) | 0.0094 (10) | 0.0048 (9) |
N1B | 0.0293 (8) | 0.0259 (7) | 0.0324 (9) | 0.0046 (6) | 0.0077 (7) | 0.0047 (6) |
C2B | 0.0285 (9) | 0.0254 (8) | 0.0239 (9) | 0.0026 (7) | 0.0004 (7) | −0.0011 (7) |
C3B | 0.0274 (9) | 0.0259 (8) | 0.0230 (9) | 0.0000 (7) | 0.0007 (7) | −0.0019 (7) |
C4B | 0.0290 (10) | 0.0335 (9) | 0.0223 (9) | 0.0015 (8) | 0.0030 (7) | −0.0020 (7) |
C5B | 0.0307 (10) | 0.0295 (9) | 0.0370 (11) | 0.0068 (8) | 0.0053 (8) | −0.0002 (8) |
C6B | 0.0305 (10) | 0.0246 (8) | 0.0289 (10) | 0.0023 (7) | 0.0000 (8) | 0.0001 (7) |
C13B | 0.0345 (10) | 0.0280 (9) | 0.0308 (10) | −0.0021 (8) | 0.0028 (8) | 0.0009 (7) |
C21B | 0.0291 (9) | 0.0259 (8) | 0.0229 (9) | 0.0020 (7) | 0.0059 (7) | 0.0038 (7) |
C22B | 0.0356 (10) | 0.0308 (9) | 0.0260 (10) | 0.0006 (8) | 0.0030 (8) | −0.0003 (7) |
C23B | 0.0299 (10) | 0.0477 (11) | 0.0264 (10) | 0.0000 (9) | −0.0003 (8) | 0.0048 (8) |
C24B | 0.0338 (10) | 0.0422 (11) | 0.0356 (11) | 0.0100 (9) | 0.0078 (9) | 0.0101 (9) |
C25B | 0.0423 (11) | 0.0288 (9) | 0.0430 (12) | 0.0092 (8) | 0.0111 (9) | 0.0008 (8) |
C26B | 0.0338 (10) | 0.0298 (9) | 0.0334 (10) | 0.0019 (8) | 0.0041 (8) | −0.0026 (8) |
C31B | 0.0260 (9) | 0.0305 (9) | 0.0354 (11) | 0.0068 (7) | 0.0043 (8) | 0.0092 (8) |
C32B | 0.0374 (11) | 0.0545 (13) | 0.0340 (11) | 0.0056 (10) | 0.0033 (9) | 0.0087 (10) |
C33B | 0.0589 (15) | 0.0794 (17) | 0.0346 (13) | 0.0313 (14) | 0.0113 (11) | 0.0167 (12) |
C34B | 0.0725 (19) | 0.0713 (18) | 0.075 (2) | 0.0380 (15) | 0.0477 (16) | 0.0439 (16) |
C35B | 0.0626 (17) | 0.0534 (15) | 0.111 (3) | 0.0014 (13) | 0.0478 (18) | 0.0283 (17) |
C36B | 0.0422 (12) | 0.0402 (12) | 0.0706 (16) | −0.0054 (10) | 0.0148 (12) | 0.0075 (11) |
C61B | 0.0297 (9) | 0.0252 (9) | 0.0324 (10) | 0.0059 (7) | 0.0024 (8) | 0.0036 (7) |
C62B | 0.0477 (12) | 0.0332 (10) | 0.0364 (12) | −0.0031 (9) | −0.0022 (9) | 0.0042 (8) |
C63B | 0.0610 (14) | 0.0415 (12) | 0.0405 (12) | −0.0029 (10) | −0.0008 (11) | 0.0137 (10) |
C64B | 0.0461 (12) | 0.0313 (10) | 0.0559 (14) | −0.0024 (9) | 0.0022 (10) | 0.0115 (10) |
C65B | 0.0564 (14) | 0.0355 (11) | 0.0533 (14) | −0.0110 (10) | −0.0057 (11) | 0.0017 (10) |
C66B | 0.0524 (13) | 0.0366 (11) | 0.0375 (12) | −0.0057 (10) | −0.0055 (10) | 0.0045 (9) |
Geometric parameters (Å, º) top
O4A—C4A | 1.214 (2) | C64A—H64A | 0.9500 |
N1A—C2A | 1.469 (2) | C65A—H65A | 0.9500 |
N1A—C6A | 1.466 (2) | C66A—H66A | 0.9500 |
N1A—H1A | 0.876 (19) | N1B—H1B | 0.90 (2) |
C2A—C3A | 1.550 (2) | C2B—C3B | 1.549 (2) |
C2A—C21A | 1.513 (2) | C2B—C21B | 1.513 (2) |
C3A—C4A | 1.515 (2) | C3B—C4B | 1.514 (2) |
C3A—C13A | 1.529 (2) | C3B—C13B | 1.525 (2) |
C4A—C5A | 1.503 (3) | C4B—C5B | 1.501 (3) |
O4B—C4B | 1.214 (2) | C5B—C6B | 1.532 (3) |
C5A—C6A | 1.537 (3) | C6B—C61B | 1.512 (2) |
C6A—C61A | 1.514 (2) | C13B—C31B | 1.503 (3) |
C13A—C31A | 1.510 (2) | C21B—C26B | 1.385 (2) |
C21A—C22A | 1.394 (2) | C21B—C22B | 1.390 (2) |
C21A—C26A | 1.386 (2) | C22B—C23B | 1.387 (3) |
C22A—C23A | 1.386 (3) | C23B—C24B | 1.378 (3) |
C23A—C24A | 1.377 (3) | C24B—C25B | 1.375 (3) |
C24A—C25A | 1.379 (3) | C25B—C26B | 1.387 (3) |
C25A—C26A | 1.386 (3) | C31B—C32B | 1.377 (3) |
C31A—C32A | 1.380 (3) | C31B—C36B | 1.388 (3) |
C31A—C36A | 1.387 (2) | C32B—C33B | 1.381 (3) |
C32A—C33A | 1.382 (3) | C33B—C34B | 1.369 (4) |
C33A—C34A | 1.375 (3) | C34B—C35B | 1.376 (5) |
C34A—C35A | 1.370 (3) | C35B—C36B | 1.376 (4) |
C35A—C36A | 1.384 (3) | C61B—C66B | 1.385 (3) |
C61A—C66A | 1.384 (3) | C61B—C62B | 1.378 (3) |
C61A—C62A | 1.376 (3) | C62B—C63B | 1.385 (3) |
C62A—C63A | 1.383 (3) | C63B—C64B | 1.369 (3) |
C63A—C64A | 1.368 (3) | C64B—C65B | 1.374 (3) |
C64A—C65A | 1.372 (3) | C65B—C66B | 1.381 (3) |
C65A—C66A | 1.384 (3) | C2B—H2B | 1.0000 |
N1B—C2B | 1.468 (2) | C3B—H3B | 1.0000 |
N1B—C6B | 1.466 (2) | C5B—H5C | 0.9900 |
C2A—H2A | 1.0000 | C5B—H5D | 0.9900 |
C3A—H3A | 1.0000 | C6B—H6B | 1.0000 |
C5A—H5B | 0.9900 | C13B—H13C | 0.9900 |
C5A—H5A | 0.9900 | C13B—H13D | 0.9900 |
C6A—H6A | 1.0000 | C22B—H22B | 0.9500 |
C13A—H13A | 0.9900 | C23B—H23B | 0.9500 |
C13A—H13B | 0.9900 | C24B—H24B | 0.9500 |
C22A—H22A | 0.9500 | C25B—H25B | 0.9500 |
C23A—H23A | 0.9500 | C26B—H26B | 0.9500 |
C24A—H24A | 0.9500 | C32B—H32B | 0.9500 |
C25A—H25A | 0.9500 | C33B—H33B | 0.9500 |
C26A—H26A | 0.9500 | C34B—H34B | 0.9500 |
C32A—H32A | 0.9500 | C35B—H35B | 0.9500 |
C33A—H33A | 0.9500 | C36B—H36B | 0.9500 |
C34A—H34A | 0.9500 | C62B—H62B | 0.9500 |
C35A—H35A | 0.9500 | C63B—H63B | 0.9500 |
C36A—H36A | 0.9500 | C64B—H64B | 0.9500 |
C62A—H62A | 0.9500 | C65B—H65B | 0.9500 |
C63A—H63A | 0.9500 | C66B—H66B | 0.9500 |
| | | |
C2A—N1A—C6A | 114.30 (13) | C65A—C66A—H66A | 120.00 |
C2A—N1A—H1A | 105.9 (12) | C2B—N1B—H1B | 106.4 (14) |
C6A—N1A—H1A | 107.7 (13) | C6B—N1B—H1B | 108.2 (13) |
C3A—C2A—C21A | 111.90 (14) | C3B—C2B—C21B | 112.05 (14) |
N1A—C2A—C3A | 109.14 (13) | N1B—C2B—C3B | 109.53 (13) |
N1A—C2A—C21A | 108.24 (13) | N1B—C2B—C21B | 109.00 (13) |
C2A—C3A—C4A | 107.30 (13) | C2B—C3B—C4B | 107.58 (14) |
C2A—C3A—C13A | 112.08 (13) | C2B—C3B—C13B | 111.16 (13) |
C4A—C3A—C13A | 112.91 (15) | C4B—C3B—C13B | 112.72 (14) |
O4A—C4A—C3A | 122.72 (16) | O4B—C4B—C3B | 122.62 (16) |
C3A—C4A—C5A | 114.66 (15) | C3B—C4B—C5B | 114.85 (15) |
O4A—C4A—C5A | 122.40 (16) | O4B—C4B—C5B | 122.22 (16) |
C4A—C5A—C6A | 108.12 (14) | C4B—C5B—C6B | 107.83 (14) |
N1A—C6A—C61A | 108.91 (14) | N1B—C6B—C61B | 108.48 (14) |
C5A—C6A—C61A | 113.16 (14) | C5B—C6B—C61B | 114.23 (14) |
N1A—C6A—C5A | 107.85 (14) | N1B—C6B—C5B | 107.88 (14) |
C3A—C13A—C31A | 114.52 (14) | C3B—C13B—C31B | 117.21 (15) |
C2A—C21A—C26A | 120.59 (15) | C2B—C21B—C26B | 120.72 (15) |
C2A—C21A—C22A | 120.96 (14) | C2B—C21B—C22B | 120.63 (14) |
C22A—C21A—C26A | 118.45 (16) | C22B—C21B—C26B | 118.64 (16) |
C21A—C22A—C23A | 120.63 (17) | C21B—C22B—C23B | 120.33 (16) |
C22A—C23A—C24A | 120.13 (18) | C22B—C23B—C24B | 120.23 (17) |
C23A—C24A—C25A | 119.87 (18) | C23B—C24B—C25B | 120.01 (18) |
C24A—C25A—C26A | 120.13 (18) | C24B—C25B—C26B | 119.81 (17) |
C21A—C26A—C25A | 120.79 (17) | C21B—C26B—C25B | 120.94 (17) |
C13A—C31A—C32A | 120.87 (16) | C13B—C31B—C32B | 122.60 (17) |
C32A—C31A—C36A | 117.82 (17) | C32B—C31B—C36B | 117.86 (19) |
C13A—C31A—C36A | 121.24 (16) | C13B—C31B—C36B | 119.42 (18) |
C31A—C32A—C33A | 121.30 (18) | C31B—C32B—C33B | 121.1 (2) |
C32A—C33A—C34A | 120.18 (19) | C32B—C33B—C34B | 120.5 (2) |
C33A—C34A—C35A | 119.39 (19) | C33B—C34B—C35B | 119.3 (3) |
C34A—C35A—C36A | 120.45 (18) | C34B—C35B—C36B | 120.3 (3) |
C31A—C36A—C35A | 120.87 (17) | C31B—C36B—C35B | 121.0 (2) |
C6A—C61A—C62A | 120.49 (16) | C6B—C61B—C62B | 120.65 (16) |
C62A—C61A—C66A | 118.35 (16) | C62B—C61B—C66B | 118.05 (16) |
C6A—C61A—C66A | 121.10 (16) | C6B—C61B—C66B | 121.19 (16) |
C61A—C62A—C63A | 120.81 (19) | C61B—C62B—C63B | 121.11 (18) |
C62A—C63A—C64A | 120.4 (2) | C62B—C63B—C64B | 120.2 (2) |
C63A—C64A—C65A | 119.6 (2) | C63B—C64B—C65B | 119.4 (2) |
C64A—C65A—C66A | 120.1 (2) | C64B—C65B—C66B | 120.4 (2) |
C61A—C66A—C65A | 120.76 (19) | C61B—C66B—C65B | 120.77 (19) |
C2B—N1B—C6B | 113.60 (13) | N1B—C2B—H2B | 109.00 |
C3A—C2A—H2A | 109.00 | C3B—C2B—H2B | 109.00 |
C21A—C2A—H2A | 109.00 | C21B—C2B—H2B | 109.00 |
N1A—C2A—H2A | 109.00 | C2B—C3B—H3B | 108.00 |
C4A—C3A—H3A | 108.00 | C4B—C3B—H3B | 108.00 |
C13A—C3A—H3A | 108.00 | C13B—C3B—H3B | 108.00 |
C2A—C3A—H3A | 108.00 | C4B—C5B—H5C | 110.00 |
C4A—C5A—H5A | 110.00 | C4B—C5B—H5D | 110.00 |
C4A—C5A—H5B | 110.00 | C6B—C5B—H5C | 110.00 |
C6A—C5A—H5B | 110.00 | C6B—C5B—H5D | 110.00 |
H5A—C5A—H5B | 108.00 | H5C—C5B—H5D | 108.00 |
C6A—C5A—H5A | 110.00 | N1B—C6B—H6B | 109.00 |
C5A—C6A—H6A | 109.00 | C5B—C6B—H6B | 109.00 |
C61A—C6A—H6A | 109.00 | C61B—C6B—H6B | 109.00 |
N1A—C6A—H6A | 109.00 | C3B—C13B—H13C | 108.00 |
C3A—C13A—H13A | 109.00 | C3B—C13B—H13D | 108.00 |
C31A—C13A—H13A | 109.00 | C31B—C13B—H13C | 108.00 |
C31A—C13A—H13B | 109.00 | C31B—C13B—H13D | 108.00 |
C3A—C13A—H13B | 109.00 | H13C—C13B—H13D | 107.00 |
H13A—C13A—H13B | 108.00 | C21B—C22B—H22B | 120.00 |
C23A—C22A—H22A | 120.00 | C23B—C22B—H22B | 120.00 |
C21A—C22A—H22A | 120.00 | C22B—C23B—H23B | 120.00 |
C24A—C23A—H23A | 120.00 | C24B—C23B—H23B | 120.00 |
C22A—C23A—H23A | 120.00 | C23B—C24B—H24B | 120.00 |
C23A—C24A—H24A | 120.00 | C25B—C24B—H24B | 120.00 |
C25A—C24A—H24A | 120.00 | C24B—C25B—H25B | 120.00 |
C24A—C25A—H25A | 120.00 | C26B—C25B—H25B | 120.00 |
C26A—C25A—H25A | 120.00 | C21B—C26B—H26B | 120.00 |
C25A—C26A—H26A | 120.00 | C25B—C26B—H26B | 120.00 |
C21A—C26A—H26A | 120.00 | C31B—C32B—H32B | 119.00 |
C31A—C32A—H32A | 119.00 | C33B—C32B—H32B | 119.00 |
C33A—C32A—H32A | 119.00 | C32B—C33B—H33B | 120.00 |
C34A—C33A—H33A | 120.00 | C34B—C33B—H33B | 120.00 |
C32A—C33A—H33A | 120.00 | C33B—C34B—H34B | 120.00 |
C33A—C34A—H34A | 120.00 | C35B—C34B—H34B | 120.00 |
C35A—C34A—H34A | 120.00 | C34B—C35B—H35B | 120.00 |
C36A—C35A—H35A | 120.00 | C36B—C35B—H35B | 120.00 |
C34A—C35A—H35A | 120.00 | C31B—C36B—H36B | 119.00 |
C31A—C36A—H36A | 120.00 | C35B—C36B—H36B | 120.00 |
C35A—C36A—H36A | 120.00 | C61B—C62B—H62B | 119.00 |
C63A—C62A—H62A | 120.00 | C63B—C62B—H62B | 119.00 |
C61A—C62A—H62A | 120.00 | C62B—C63B—H63B | 120.00 |
C62A—C63A—H63A | 120.00 | C64B—C63B—H63B | 120.00 |
C64A—C63A—H63A | 120.00 | C63B—C64B—H64B | 120.00 |
C65A—C64A—H64A | 120.00 | C65B—C64B—H64B | 120.00 |
C63A—C64A—H64A | 120.00 | C64B—C65B—H65B | 120.00 |
C64A—C65A—H65A | 120.00 | C66B—C65B—H65B | 120.00 |
C66A—C65A—H65A | 120.00 | C61B—C66B—H66B | 120.00 |
C61A—C66A—H66A | 120.00 | C65B—C66B—H66B | 120.00 |
| | | |
C6A—N1A—C2A—C3A | 61.46 (18) | C6B—N1B—C2B—C3B | 61.29 (18) |
C6A—N1A—C2A—C21A | −176.53 (14) | C6B—N1B—C2B—C21B | −175.80 (14) |
C2A—N1A—C6A—C5A | −62.31 (18) | C2B—N1B—C6B—C5B | −63.35 (18) |
C2A—N1A—C6A—C61A | 174.52 (14) | C2B—N1B—C6B—C61B | 172.43 (14) |
C21A—C2A—C3A—C4A | −173.88 (13) | C21B—C2B—C3B—C4B | −174.28 (13) |
N1A—C2A—C3A—C4A | −54.10 (17) | N1B—C2B—C3B—C4B | −53.20 (17) |
N1A—C2A—C3A—C13A | −178.60 (14) | N1B—C2B—C3B—C13B | −177.05 (14) |
N1A—C2A—C21A—C26A | 133.69 (16) | N1B—C2B—C21B—C26B | 135.23 (16) |
C3A—C2A—C21A—C22A | 74.08 (19) | C3B—C2B—C21B—C22B | 75.98 (19) |
C3A—C2A—C21A—C26A | −106.01 (18) | C3B—C2B—C21B—C26B | −103.38 (18) |
C21A—C2A—C3A—C13A | 61.62 (18) | C21B—C2B—C3B—C13B | 61.87 (18) |
N1A—C2A—C21A—C22A | −46.2 (2) | N1B—C2B—C21B—C22B | −45.4 (2) |
C13A—C3A—C4A—O4A | 5.2 (2) | C13B—C3B—C4B—O4B | 4.0 (2) |
C2A—C3A—C4A—O4A | −118.79 (18) | C2B—C3B—C4B—O4B | −118.88 (18) |
C2A—C3A—C4A—C5A | 55.97 (18) | C2B—C3B—C4B—C5B | 54.85 (18) |
C4A—C3A—C13A—C31A | 75.06 (19) | C4B—C3B—C13B—C31B | 68.0 (2) |
C13A—C3A—C4A—C5A | 179.96 (15) | C13B—C3B—C4B—C5B | 177.74 (15) |
C2A—C3A—C13A—C31A | −163.62 (15) | C2B—C3B—C13B—C31B | −171.14 (15) |
O4A—C4A—C5A—C6A | 116.86 (19) | O4B—C4B—C5B—C6B | 115.95 (19) |
C3A—C4A—C5A—C6A | −57.92 (19) | C3B—C4B—C5B—C6B | −57.81 (19) |
C4A—C5A—C6A—C61A | 177.43 (15) | C4B—C5B—C6B—C61B | 178.78 (15) |
C4A—C5A—C6A—N1A | 56.90 (18) | C4B—C5B—C6B—N1B | 58.09 (18) |
N1A—C6A—C61A—C62A | −129.72 (18) | N1B—C6B—C61B—C62B | −112.54 (19) |
N1A—C6A—C61A—C66A | 47.5 (2) | N1B—C6B—C61B—C66B | 63.5 (2) |
C5A—C6A—C61A—C62A | 110.35 (19) | C5B—C6B—C61B—C62B | 127.11 (18) |
C5A—C6A—C61A—C66A | −72.5 (2) | C5B—C6B—C61B—C66B | −56.8 (2) |
C3A—C13A—C31A—C32A | 51.9 (2) | C3B—C13B—C31B—C32B | 40.2 (3) |
C3A—C13A—C31A—C36A | −131.02 (17) | C3B—C13B—C31B—C36B | −143.99 (18) |
C2A—C21A—C22A—C23A | 179.95 (16) | C2B—C21B—C22B—C23B | −178.94 (16) |
C26A—C21A—C22A—C23A | 0.0 (3) | C26B—C21B—C22B—C23B | 0.4 (3) |
C2A—C21A—C26A—C25A | 179.44 (17) | C2B—C21B—C26B—C25B | 177.54 (17) |
C22A—C21A—C26A—C25A | −0.7 (3) | C22B—C21B—C26B—C25B | −1.8 (3) |
C21A—C22A—C23A—C24A | 0.9 (3) | C21B—C22B—C23B—C24B | 1.4 (3) |
C22A—C23A—C24A—C25A | −1.2 (3) | C22B—C23B—C24B—C25B | −1.9 (3) |
C23A—C24A—C25A—C26A | 0.6 (3) | C23B—C24B—C25B—C26B | 0.5 (3) |
C24A—C25A—C26A—C21A | 0.4 (3) | C24B—C25B—C26B—C21B | 1.4 (3) |
C13A—C31A—C32A—C33A | 177.01 (17) | C13B—C31B—C32B—C33B | 174.7 (2) |
C36A—C31A—C32A—C33A | −0.2 (3) | C36B—C31B—C32B—C33B | −1.2 (3) |
C13A—C31A—C36A—C35A | −176.97 (16) | C13B—C31B—C36B—C35B | −175.8 (2) |
C32A—C31A—C36A—C35A | 0.2 (2) | C32B—C31B—C36B—C35B | 0.2 (3) |
C31A—C32A—C33A—C34A | 0.1 (3) | C31B—C32B—C33B—C34B | 0.8 (4) |
C32A—C33A—C34A—C35A | −0.1 (3) | C32B—C33B—C34B—C35B | 0.7 (4) |
C33A—C34A—C35A—C36A | 0.1 (3) | C33B—C34B—C35B—C36B | −1.7 (4) |
C34A—C35A—C36A—C31A | −0.2 (3) | C34B—C35B—C36B—C31B | 1.3 (4) |
C6A—C61A—C62A—C63A | 176.43 (19) | C6B—C61B—C62B—C63B | 175.47 (17) |
C66A—C61A—C62A—C63A | −0.9 (3) | C66B—C61B—C62B—C63B | −0.7 (3) |
C6A—C61A—C66A—C65A | −176.76 (18) | C6B—C61B—C66B—C65B | −176.13 (17) |
C62A—C61A—C66A—C65A | 0.5 (3) | C62B—C61B—C66B—C65B | 0.1 (3) |
C61A—C62A—C63A—C64A | 0.7 (3) | C61B—C62B—C63B—C64B | 1.0 (3) |
C62A—C63A—C64A—C65A | −0.2 (4) | C62B—C63B—C64B—C65B | −0.6 (3) |
C63A—C64A—C65A—C66A | −0.1 (3) | C63B—C64B—C65B—C66B | −0.1 (3) |
C64A—C65A—C66A—C61A | 0.0 (3) | C64B—C65B—C66B—C61B | 0.4 (3) |
Hydrogen-bond geometry (Å, º) topCg2, Cg3, Cg6 and Cg7 are the centroids of phenyl rings
C21A–C26A, C31A–C36A, C21B–C26B and
C31B–C36B,
respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O4Bi | 0.88 (2) | 2.41 (2) | 3.234 (2) | 158 (2) |
N1B—H1B···O4Aii | 0.90 (2) | 2.48 (2) | 3.315 (2) | 153 (2) |
C2A—H2A···Cg6iii | 1.00 | 2.95 | 3.9315 (19) | 167 |
C2B—H2B···Cg2iv | 1.00 | 3.00 | 3.9733 (19) | 166 |
C25B—H25B···Cg3v | 0.95 | 2.78 | 3.626 (2) | 150 |
C64A—H64A···Cg3ii | 0.95 | 2.78 | 3.661 (2) | 155 |
C64B—H64B···Cg7i | 0.95 | 2.93 | 3.796 (2) | 153 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2. |