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The asymmetric unit of the title compound, C24H23NO, 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 –ABAB– chains along [100]. In addition, five C—H...π inter­actions are also present, linking the chains to form a three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616001887/su4012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616001887/su4012Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2414314616001887/su4012Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616001887/su4012Isup4.cml
Supplementary material

CCDC reference: 1451096

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](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

Computing details top

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
C24H23NOF(000) = 1456
Mr = 341.43Dx = 1.211 Mg m3
Monoclinic, P21/nMelting point: 471 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.8918 (5) ÅCell parameters from 7035 reflections
b = 30.6042 (12) Åθ = 2.6–22.8°
c = 12.3878 (6) ŵ = 0.07 mm1
β = 92.426 (2)°T = 178 K
V = 3746.8 (3) Å3Plate, colourless
Z = 80.40 × 0.36 × 0.16 mm
Data collection top
Bruker Kappa APEXIII CCD area-detector
diffractometer
10617 independent reflections
Radiation source: fine-focus sealed tube6350 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.078
φ and ω scansθmax = 29.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 1313
Tmin = 0.81, Tmax = 0.99k = 4242
58653 measured reflectionsl = 1417
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: mixed
wR(F2) = 0.150H 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 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
O4A0.66207 (13)0.14287 (4)0.97486 (11)0.0395 (5)
N1A0.29441 (15)0.17242 (5)0.87397 (13)0.0294 (5)
C2A0.33073 (17)0.12682 (5)0.89839 (14)0.0255 (5)
C3A0.42875 (17)0.12561 (5)0.99936 (14)0.0258 (5)
C4A0.54612 (18)0.15567 (6)0.97724 (14)0.0287 (5)
O4B0.64521 (13)0.35463 (4)0.14639 (11)0.0398 (4)
C5A0.50630 (18)0.20176 (6)0.94862 (15)0.0310 (6)
C6A0.40932 (18)0.20027 (5)0.84847 (14)0.0281 (5)
C13A0.4738 (2)0.07909 (6)1.02805 (14)0.0316 (6)
C21A0.20186 (17)0.10166 (5)0.91607 (13)0.0256 (5)
C22A0.10267 (19)0.11842 (6)0.98114 (15)0.0327 (6)
C23A0.0152 (2)0.09519 (7)0.99688 (16)0.0376 (6)
C24A0.0346 (2)0.05489 (7)0.94932 (16)0.0385 (7)
C25A0.0624 (2)0.03799 (6)0.88431 (16)0.0371 (6)
C26A0.17976 (19)0.06132 (6)0.86759 (15)0.0314 (6)
C31A0.53595 (17)0.07396 (5)1.14082 (14)0.0260 (5)
C32A0.4699 (2)0.08900 (6)1.22942 (16)0.0368 (6)
C33A0.5230 (2)0.08269 (7)1.33323 (17)0.0462 (7)
C34A0.6440 (2)0.06114 (7)1.35011 (17)0.0440 (7)
C35A0.7111 (2)0.04598 (6)1.26319 (17)0.0393 (6)
C36A0.65797 (18)0.05231 (5)1.15920 (15)0.0315 (6)
C61A0.35679 (18)0.24486 (5)0.81445 (15)0.0292 (6)
C62A0.3975 (2)0.26388 (6)0.72053 (17)0.0437 (7)
C63A0.3443 (3)0.30352 (7)0.68587 (19)0.0560 (9)
C64A0.2511 (2)0.32475 (7)0.74529 (19)0.0490 (8)
C65A0.2101 (2)0.30642 (7)0.83958 (19)0.0484 (8)
C66A0.2627 (2)0.26665 (6)0.87408 (18)0.0425 (7)
N1B0.28747 (15)0.32434 (5)0.24447 (13)0.0290 (5)
C2B0.31937 (17)0.36986 (5)0.21806 (14)0.0260 (5)
C3B0.40928 (17)0.37099 (5)0.11867 (14)0.0254 (5)
C4B0.52943 (18)0.34139 (6)0.14279 (14)0.0282 (5)
C5B0.49399 (19)0.29549 (6)0.17362 (15)0.0323 (6)
C6B0.40709 (17)0.29780 (5)0.27294 (14)0.0280 (5)
C13B0.45080 (19)0.41762 (6)0.09216 (15)0.0311 (6)
C21B0.18873 (17)0.39485 (5)0.19832 (13)0.0258 (5)
C22B0.08347 (18)0.37718 (6)0.13450 (14)0.0308 (6)
C23B0.03523 (19)0.40058 (6)0.11528 (15)0.0347 (6)
C24B0.0486 (2)0.44195 (6)0.15741 (16)0.0370 (6)
C25B0.0544 (2)0.45969 (6)0.22133 (16)0.0378 (6)
C26B0.17202 (19)0.43595 (6)0.24253 (15)0.0323 (6)
C31B0.52074 (18)0.42469 (6)0.01175 (15)0.0306 (6)
C32B0.4822 (2)0.40348 (7)0.10618 (16)0.0419 (7)
C33B0.5413 (3)0.41335 (9)0.20217 (18)0.0574 (9)
C34B0.6411 (3)0.44425 (10)0.2052 (3)0.0717 (11)
C35B0.6830 (3)0.46507 (9)0.1112 (3)0.0744 (13)
C36B0.6227 (2)0.45573 (7)0.0158 (2)0.0507 (8)
C61B0.36041 (18)0.25385 (5)0.31273 (15)0.0291 (5)
C62B0.3830 (2)0.24185 (6)0.41921 (16)0.0392 (7)
C63B0.3325 (2)0.20300 (7)0.45824 (18)0.0478 (7)
C64B0.2605 (2)0.17535 (7)0.39071 (18)0.0444 (7)
C65B0.2378 (2)0.18668 (7)0.28414 (19)0.0486 (8)
C66B0.2869 (2)0.22564 (6)0.24535 (17)0.0424 (7)
H1A0.2395 (19)0.1715 (6)0.8167 (16)0.032 (5)*
H2A0.376920.113990.835500.0306*
H3A0.380180.137761.061850.0310*
H5A0.587610.219140.933060.0372*
H5B0.461130.215591.009710.0372*
H6A0.457400.186950.787150.0338*
H13A0.394490.059461.020030.0379*
H13B0.540560.069500.975620.0379*
H22A0.115940.146031.015010.0392*
H23A0.082640.107101.040590.0451*
H24A0.114670.038760.961260.0461*
H25A0.048710.010300.850920.0445*
H26A0.245840.049530.822360.0376*
H32A0.386240.103991.218850.0441*
H33A0.475740.093271.393090.0554*
H34A0.680700.056811.421410.0528*
H35A0.794660.031021.274350.0471*
H36A0.705710.041691.099640.0378*
H62A0.462880.249610.678980.0523*
H63A0.372630.316070.620440.0672*
H64A0.214910.352020.721430.0588*
H65A0.145610.321050.881250.0580*
H66A0.233870.254170.939450.0510*
H1B0.235 (2)0.3253 (7)0.3023 (18)0.050 (7)*
H2B0.370690.383230.281030.0312*
H3B0.356000.358850.055140.0305*
H5C0.443170.280960.113140.0387*
H5D0.577360.278490.190600.0387*
H6B0.460290.312640.332800.0336*
H13C0.511340.428360.152100.0373*
H13D0.368510.436060.090580.0373*
H22B0.092850.348930.103900.0369*
H23B0.107550.388050.072930.0417*
H24B0.128970.458210.142300.0444*
H25B0.045010.488120.250880.0453*
H26B0.242090.448070.288020.0387*
H32B0.413840.381690.105230.0503*
H33B0.512470.398600.266580.0688*
H34B0.681060.451240.271440.0860*
H35B0.753870.486000.112120.0891*
H36B0.651350.470740.048310.0608*
H62B0.433970.260560.466640.0470*
H63B0.347990.195500.532150.0573*
H64B0.226480.148570.417270.0533*
H65B0.188060.167590.236830.0583*
H66B0.270050.233180.171620.0509*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O4A0.0305 (7)0.0438 (8)0.0443 (9)0.0043 (6)0.0016 (6)0.0055 (6)
N1A0.0308 (8)0.0251 (7)0.0316 (9)0.0028 (6)0.0066 (7)0.0049 (6)
C2A0.0304 (9)0.0229 (8)0.0231 (9)0.0009 (7)0.0001 (7)0.0003 (7)
C3A0.0297 (9)0.0248 (8)0.0229 (9)0.0011 (7)0.0003 (7)0.0011 (7)
C4A0.0313 (10)0.0341 (9)0.0204 (9)0.0003 (8)0.0031 (7)0.0024 (7)
O4B0.0283 (7)0.0468 (8)0.0442 (8)0.0015 (6)0.0012 (6)0.0078 (6)
C5A0.0312 (10)0.0277 (9)0.0337 (10)0.0050 (7)0.0020 (8)0.0011 (8)
C6A0.0315 (10)0.0244 (8)0.0286 (10)0.0020 (7)0.0021 (8)0.0002 (7)
C13A0.0411 (11)0.0263 (9)0.0272 (10)0.0031 (8)0.0014 (8)0.0001 (7)
C21A0.0304 (9)0.0258 (8)0.0202 (9)0.0003 (7)0.0018 (7)0.0053 (7)
C22A0.0362 (10)0.0321 (10)0.0297 (10)0.0016 (8)0.0008 (8)0.0009 (8)
C23A0.0330 (10)0.0501 (12)0.0300 (10)0.0028 (9)0.0052 (8)0.0054 (9)
C24A0.0346 (11)0.0454 (12)0.0351 (11)0.0084 (9)0.0013 (9)0.0143 (9)
C25A0.0449 (12)0.0290 (9)0.0371 (11)0.0091 (9)0.0010 (9)0.0027 (8)
C26A0.0367 (10)0.0264 (9)0.0312 (10)0.0031 (8)0.0036 (8)0.0009 (7)
C31A0.0293 (9)0.0212 (8)0.0276 (10)0.0026 (7)0.0016 (8)0.0032 (7)
C32A0.0347 (10)0.0420 (11)0.0338 (11)0.0067 (9)0.0043 (9)0.0042 (9)
C33A0.0590 (14)0.0516 (13)0.0283 (11)0.0007 (11)0.0068 (10)0.0012 (9)
C34A0.0560 (14)0.0418 (11)0.0329 (12)0.0073 (10)0.0124 (10)0.0072 (9)
C35A0.0340 (10)0.0316 (10)0.0511 (13)0.0010 (8)0.0117 (10)0.0077 (9)
C36A0.0315 (10)0.0249 (9)0.0383 (11)0.0001 (7)0.0041 (8)0.0017 (8)
C61A0.0331 (10)0.0243 (9)0.0299 (10)0.0047 (7)0.0023 (8)0.0008 (7)
C62A0.0594 (14)0.0316 (10)0.0407 (12)0.0011 (10)0.0106 (10)0.0053 (9)
C63A0.0872 (19)0.0361 (12)0.0454 (14)0.0026 (12)0.0110 (13)0.0135 (10)
C64A0.0661 (15)0.0275 (10)0.0525 (14)0.0041 (10)0.0089 (12)0.0060 (10)
C65A0.0529 (14)0.0333 (11)0.0591 (15)0.0089 (10)0.0041 (11)0.0025 (10)
C66A0.0503 (13)0.0331 (10)0.0447 (12)0.0049 (9)0.0094 (10)0.0048 (9)
N1B0.0293 (8)0.0259 (7)0.0324 (9)0.0046 (6)0.0077 (7)0.0047 (6)
C2B0.0285 (9)0.0254 (8)0.0239 (9)0.0026 (7)0.0004 (7)0.0011 (7)
C3B0.0274 (9)0.0259 (8)0.0230 (9)0.0000 (7)0.0007 (7)0.0019 (7)
C4B0.0290 (10)0.0335 (9)0.0223 (9)0.0015 (8)0.0030 (7)0.0020 (7)
C5B0.0307 (10)0.0295 (9)0.0370 (11)0.0068 (8)0.0053 (8)0.0002 (8)
C6B0.0305 (10)0.0246 (8)0.0289 (10)0.0023 (7)0.0000 (8)0.0001 (7)
C13B0.0345 (10)0.0280 (9)0.0308 (10)0.0021 (8)0.0028 (8)0.0009 (7)
C21B0.0291 (9)0.0259 (8)0.0229 (9)0.0020 (7)0.0059 (7)0.0038 (7)
C22B0.0356 (10)0.0308 (9)0.0260 (10)0.0006 (8)0.0030 (8)0.0003 (7)
C23B0.0299 (10)0.0477 (11)0.0264 (10)0.0000 (9)0.0003 (8)0.0048 (8)
C24B0.0338 (10)0.0422 (11)0.0356 (11)0.0100 (9)0.0078 (9)0.0101 (9)
C25B0.0423 (11)0.0288 (9)0.0430 (12)0.0092 (8)0.0111 (9)0.0008 (8)
C26B0.0338 (10)0.0298 (9)0.0334 (10)0.0019 (8)0.0041 (8)0.0026 (8)
C31B0.0260 (9)0.0305 (9)0.0354 (11)0.0068 (7)0.0043 (8)0.0092 (8)
C32B0.0374 (11)0.0545 (13)0.0340 (11)0.0056 (10)0.0033 (9)0.0087 (10)
C33B0.0589 (15)0.0794 (17)0.0346 (13)0.0313 (14)0.0113 (11)0.0167 (12)
C34B0.0725 (19)0.0713 (18)0.075 (2)0.0380 (15)0.0477 (16)0.0439 (16)
C35B0.0626 (17)0.0534 (15)0.111 (3)0.0014 (13)0.0478 (18)0.0283 (17)
C36B0.0422 (12)0.0402 (12)0.0706 (16)0.0054 (10)0.0148 (12)0.0075 (11)
C61B0.0297 (9)0.0252 (9)0.0324 (10)0.0059 (7)0.0024 (8)0.0036 (7)
C62B0.0477 (12)0.0332 (10)0.0364 (12)0.0031 (9)0.0022 (9)0.0042 (8)
C63B0.0610 (14)0.0415 (12)0.0405 (12)0.0029 (10)0.0008 (11)0.0137 (10)
C64B0.0461 (12)0.0313 (10)0.0559 (14)0.0024 (9)0.0022 (10)0.0115 (10)
C65B0.0564 (14)0.0355 (11)0.0533 (14)0.0110 (10)0.0057 (11)0.0017 (10)
C66B0.0524 (13)0.0366 (11)0.0375 (12)0.0057 (10)0.0055 (10)0.0045 (9)
Geometric parameters (Å, º) top
O4A—C4A1.214 (2)C64A—H64A0.9500
N1A—C2A1.469 (2)C65A—H65A0.9500
N1A—C6A1.466 (2)C66A—H66A0.9500
N1A—H1A0.876 (19)N1B—H1B0.90 (2)
C2A—C3A1.550 (2)C2B—C3B1.549 (2)
C2A—C21A1.513 (2)C2B—C21B1.513 (2)
C3A—C4A1.515 (2)C3B—C4B1.514 (2)
C3A—C13A1.529 (2)C3B—C13B1.525 (2)
C4A—C5A1.503 (3)C4B—C5B1.501 (3)
O4B—C4B1.214 (2)C5B—C6B1.532 (3)
C5A—C6A1.537 (3)C6B—C61B1.512 (2)
C6A—C61A1.514 (2)C13B—C31B1.503 (3)
C13A—C31A1.510 (2)C21B—C26B1.385 (2)
C21A—C22A1.394 (2)C21B—C22B1.390 (2)
C21A—C26A1.386 (2)C22B—C23B1.387 (3)
C22A—C23A1.386 (3)C23B—C24B1.378 (3)
C23A—C24A1.377 (3)C24B—C25B1.375 (3)
C24A—C25A1.379 (3)C25B—C26B1.387 (3)
C25A—C26A1.386 (3)C31B—C32B1.377 (3)
C31A—C32A1.380 (3)C31B—C36B1.388 (3)
C31A—C36A1.387 (2)C32B—C33B1.381 (3)
C32A—C33A1.382 (3)C33B—C34B1.369 (4)
C33A—C34A1.375 (3)C34B—C35B1.376 (5)
C34A—C35A1.370 (3)C35B—C36B1.376 (4)
C35A—C36A1.384 (3)C61B—C66B1.385 (3)
C61A—C66A1.384 (3)C61B—C62B1.378 (3)
C61A—C62A1.376 (3)C62B—C63B1.385 (3)
C62A—C63A1.383 (3)C63B—C64B1.369 (3)
C63A—C64A1.368 (3)C64B—C65B1.374 (3)
C64A—C65A1.372 (3)C65B—C66B1.381 (3)
C65A—C66A1.384 (3)C2B—H2B1.0000
N1B—C2B1.468 (2)C3B—H3B1.0000
N1B—C6B1.466 (2)C5B—H5C0.9900
C2A—H2A1.0000C5B—H5D0.9900
C3A—H3A1.0000C6B—H6B1.0000
C5A—H5B0.9900C13B—H13C0.9900
C5A—H5A0.9900C13B—H13D0.9900
C6A—H6A1.0000C22B—H22B0.9500
C13A—H13A0.9900C23B—H23B0.9500
C13A—H13B0.9900C24B—H24B0.9500
C22A—H22A0.9500C25B—H25B0.9500
C23A—H23A0.9500C26B—H26B0.9500
C24A—H24A0.9500C32B—H32B0.9500
C25A—H25A0.9500C33B—H33B0.9500
C26A—H26A0.9500C34B—H34B0.9500
C32A—H32A0.9500C35B—H35B0.9500
C33A—H33A0.9500C36B—H36B0.9500
C34A—H34A0.9500C62B—H62B0.9500
C35A—H35A0.9500C63B—H63B0.9500
C36A—H36A0.9500C64B—H64B0.9500
C62A—H62A0.9500C65B—H65B0.9500
C63A—H63A0.9500C66B—H66B0.9500
C2A—N1A—C6A114.30 (13)C65A—C66A—H66A120.00
C2A—N1A—H1A105.9 (12)C2B—N1B—H1B106.4 (14)
C6A—N1A—H1A107.7 (13)C6B—N1B—H1B108.2 (13)
C3A—C2A—C21A111.90 (14)C3B—C2B—C21B112.05 (14)
N1A—C2A—C3A109.14 (13)N1B—C2B—C3B109.53 (13)
N1A—C2A—C21A108.24 (13)N1B—C2B—C21B109.00 (13)
C2A—C3A—C4A107.30 (13)C2B—C3B—C4B107.58 (14)
C2A—C3A—C13A112.08 (13)C2B—C3B—C13B111.16 (13)
C4A—C3A—C13A112.91 (15)C4B—C3B—C13B112.72 (14)
O4A—C4A—C3A122.72 (16)O4B—C4B—C3B122.62 (16)
C3A—C4A—C5A114.66 (15)C3B—C4B—C5B114.85 (15)
O4A—C4A—C5A122.40 (16)O4B—C4B—C5B122.22 (16)
C4A—C5A—C6A108.12 (14)C4B—C5B—C6B107.83 (14)
N1A—C6A—C61A108.91 (14)N1B—C6B—C61B108.48 (14)
C5A—C6A—C61A113.16 (14)C5B—C6B—C61B114.23 (14)
N1A—C6A—C5A107.85 (14)N1B—C6B—C5B107.88 (14)
C3A—C13A—C31A114.52 (14)C3B—C13B—C31B117.21 (15)
C2A—C21A—C26A120.59 (15)C2B—C21B—C26B120.72 (15)
C2A—C21A—C22A120.96 (14)C2B—C21B—C22B120.63 (14)
C22A—C21A—C26A118.45 (16)C22B—C21B—C26B118.64 (16)
C21A—C22A—C23A120.63 (17)C21B—C22B—C23B120.33 (16)
C22A—C23A—C24A120.13 (18)C22B—C23B—C24B120.23 (17)
C23A—C24A—C25A119.87 (18)C23B—C24B—C25B120.01 (18)
C24A—C25A—C26A120.13 (18)C24B—C25B—C26B119.81 (17)
C21A—C26A—C25A120.79 (17)C21B—C26B—C25B120.94 (17)
C13A—C31A—C32A120.87 (16)C13B—C31B—C32B122.60 (17)
C32A—C31A—C36A117.82 (17)C32B—C31B—C36B117.86 (19)
C13A—C31A—C36A121.24 (16)C13B—C31B—C36B119.42 (18)
C31A—C32A—C33A121.30 (18)C31B—C32B—C33B121.1 (2)
C32A—C33A—C34A120.18 (19)C32B—C33B—C34B120.5 (2)
C33A—C34A—C35A119.39 (19)C33B—C34B—C35B119.3 (3)
C34A—C35A—C36A120.45 (18)C34B—C35B—C36B120.3 (3)
C31A—C36A—C35A120.87 (17)C31B—C36B—C35B121.0 (2)
C6A—C61A—C62A120.49 (16)C6B—C61B—C62B120.65 (16)
C62A—C61A—C66A118.35 (16)C62B—C61B—C66B118.05 (16)
C6A—C61A—C66A121.10 (16)C6B—C61B—C66B121.19 (16)
C61A—C62A—C63A120.81 (19)C61B—C62B—C63B121.11 (18)
C62A—C63A—C64A120.4 (2)C62B—C63B—C64B120.2 (2)
C63A—C64A—C65A119.6 (2)C63B—C64B—C65B119.4 (2)
C64A—C65A—C66A120.1 (2)C64B—C65B—C66B120.4 (2)
C61A—C66A—C65A120.76 (19)C61B—C66B—C65B120.77 (19)
C2B—N1B—C6B113.60 (13)N1B—C2B—H2B109.00
C3A—C2A—H2A109.00C3B—C2B—H2B109.00
C21A—C2A—H2A109.00C21B—C2B—H2B109.00
N1A—C2A—H2A109.00C2B—C3B—H3B108.00
C4A—C3A—H3A108.00C4B—C3B—H3B108.00
C13A—C3A—H3A108.00C13B—C3B—H3B108.00
C2A—C3A—H3A108.00C4B—C5B—H5C110.00
C4A—C5A—H5A110.00C4B—C5B—H5D110.00
C4A—C5A—H5B110.00C6B—C5B—H5C110.00
C6A—C5A—H5B110.00C6B—C5B—H5D110.00
H5A—C5A—H5B108.00H5C—C5B—H5D108.00
C6A—C5A—H5A110.00N1B—C6B—H6B109.00
C5A—C6A—H6A109.00C5B—C6B—H6B109.00
C61A—C6A—H6A109.00C61B—C6B—H6B109.00
N1A—C6A—H6A109.00C3B—C13B—H13C108.00
C3A—C13A—H13A109.00C3B—C13B—H13D108.00
C31A—C13A—H13A109.00C31B—C13B—H13C108.00
C31A—C13A—H13B109.00C31B—C13B—H13D108.00
C3A—C13A—H13B109.00H13C—C13B—H13D107.00
H13A—C13A—H13B108.00C21B—C22B—H22B120.00
C23A—C22A—H22A120.00C23B—C22B—H22B120.00
C21A—C22A—H22A120.00C22B—C23B—H23B120.00
C24A—C23A—H23A120.00C24B—C23B—H23B120.00
C22A—C23A—H23A120.00C23B—C24B—H24B120.00
C23A—C24A—H24A120.00C25B—C24B—H24B120.00
C25A—C24A—H24A120.00C24B—C25B—H25B120.00
C24A—C25A—H25A120.00C26B—C25B—H25B120.00
C26A—C25A—H25A120.00C21B—C26B—H26B120.00
C25A—C26A—H26A120.00C25B—C26B—H26B120.00
C21A—C26A—H26A120.00C31B—C32B—H32B119.00
C31A—C32A—H32A119.00C33B—C32B—H32B119.00
C33A—C32A—H32A119.00C32B—C33B—H33B120.00
C34A—C33A—H33A120.00C34B—C33B—H33B120.00
C32A—C33A—H33A120.00C33B—C34B—H34B120.00
C33A—C34A—H34A120.00C35B—C34B—H34B120.00
C35A—C34A—H34A120.00C34B—C35B—H35B120.00
C36A—C35A—H35A120.00C36B—C35B—H35B120.00
C34A—C35A—H35A120.00C31B—C36B—H36B119.00
C31A—C36A—H36A120.00C35B—C36B—H36B120.00
C35A—C36A—H36A120.00C61B—C62B—H62B119.00
C63A—C62A—H62A120.00C63B—C62B—H62B119.00
C61A—C62A—H62A120.00C62B—C63B—H63B120.00
C62A—C63A—H63A120.00C64B—C63B—H63B120.00
C64A—C63A—H63A120.00C63B—C64B—H64B120.00
C65A—C64A—H64A120.00C65B—C64B—H64B120.00
C63A—C64A—H64A120.00C64B—C65B—H65B120.00
C64A—C65A—H65A120.00C66B—C65B—H65B120.00
C66A—C65A—H65A120.00C61B—C66B—H66B120.00
C61A—C66A—H66A120.00C65B—C66B—H66B120.00
C6A—N1A—C2A—C3A61.46 (18)C6B—N1B—C2B—C3B61.29 (18)
C6A—N1A—C2A—C21A176.53 (14)C6B—N1B—C2B—C21B175.80 (14)
C2A—N1A—C6A—C5A62.31 (18)C2B—N1B—C6B—C5B63.35 (18)
C2A—N1A—C6A—C61A174.52 (14)C2B—N1B—C6B—C61B172.43 (14)
C21A—C2A—C3A—C4A173.88 (13)C21B—C2B—C3B—C4B174.28 (13)
N1A—C2A—C3A—C4A54.10 (17)N1B—C2B—C3B—C4B53.20 (17)
N1A—C2A—C3A—C13A178.60 (14)N1B—C2B—C3B—C13B177.05 (14)
N1A—C2A—C21A—C26A133.69 (16)N1B—C2B—C21B—C26B135.23 (16)
C3A—C2A—C21A—C22A74.08 (19)C3B—C2B—C21B—C22B75.98 (19)
C3A—C2A—C21A—C26A106.01 (18)C3B—C2B—C21B—C26B103.38 (18)
C21A—C2A—C3A—C13A61.62 (18)C21B—C2B—C3B—C13B61.87 (18)
N1A—C2A—C21A—C22A46.2 (2)N1B—C2B—C21B—C22B45.4 (2)
C13A—C3A—C4A—O4A5.2 (2)C13B—C3B—C4B—O4B4.0 (2)
C2A—C3A—C4A—O4A118.79 (18)C2B—C3B—C4B—O4B118.88 (18)
C2A—C3A—C4A—C5A55.97 (18)C2B—C3B—C4B—C5B54.85 (18)
C4A—C3A—C13A—C31A75.06 (19)C4B—C3B—C13B—C31B68.0 (2)
C13A—C3A—C4A—C5A179.96 (15)C13B—C3B—C4B—C5B177.74 (15)
C2A—C3A—C13A—C31A163.62 (15)C2B—C3B—C13B—C31B171.14 (15)
O4A—C4A—C5A—C6A116.86 (19)O4B—C4B—C5B—C6B115.95 (19)
C3A—C4A—C5A—C6A57.92 (19)C3B—C4B—C5B—C6B57.81 (19)
C4A—C5A—C6A—C61A177.43 (15)C4B—C5B—C6B—C61B178.78 (15)
C4A—C5A—C6A—N1A56.90 (18)C4B—C5B—C6B—N1B58.09 (18)
N1A—C6A—C61A—C62A129.72 (18)N1B—C6B—C61B—C62B112.54 (19)
N1A—C6A—C61A—C66A47.5 (2)N1B—C6B—C61B—C66B63.5 (2)
C5A—C6A—C61A—C62A110.35 (19)C5B—C6B—C61B—C62B127.11 (18)
C5A—C6A—C61A—C66A72.5 (2)C5B—C6B—C61B—C66B56.8 (2)
C3A—C13A—C31A—C32A51.9 (2)C3B—C13B—C31B—C32B40.2 (3)
C3A—C13A—C31A—C36A131.02 (17)C3B—C13B—C31B—C36B143.99 (18)
C2A—C21A—C22A—C23A179.95 (16)C2B—C21B—C22B—C23B178.94 (16)
C26A—C21A—C22A—C23A0.0 (3)C26B—C21B—C22B—C23B0.4 (3)
C2A—C21A—C26A—C25A179.44 (17)C2B—C21B—C26B—C25B177.54 (17)
C22A—C21A—C26A—C25A0.7 (3)C22B—C21B—C26B—C25B1.8 (3)
C21A—C22A—C23A—C24A0.9 (3)C21B—C22B—C23B—C24B1.4 (3)
C22A—C23A—C24A—C25A1.2 (3)C22B—C23B—C24B—C25B1.9 (3)
C23A—C24A—C25A—C26A0.6 (3)C23B—C24B—C25B—C26B0.5 (3)
C24A—C25A—C26A—C21A0.4 (3)C24B—C25B—C26B—C21B1.4 (3)
C13A—C31A—C32A—C33A177.01 (17)C13B—C31B—C32B—C33B174.7 (2)
C36A—C31A—C32A—C33A0.2 (3)C36B—C31B—C32B—C33B1.2 (3)
C13A—C31A—C36A—C35A176.97 (16)C13B—C31B—C36B—C35B175.8 (2)
C32A—C31A—C36A—C35A0.2 (2)C32B—C31B—C36B—C35B0.2 (3)
C31A—C32A—C33A—C34A0.1 (3)C31B—C32B—C33B—C34B0.8 (4)
C32A—C33A—C34A—C35A0.1 (3)C32B—C33B—C34B—C35B0.7 (4)
C33A—C34A—C35A—C36A0.1 (3)C33B—C34B—C35B—C36B1.7 (4)
C34A—C35A—C36A—C31A0.2 (3)C34B—C35B—C36B—C31B1.3 (4)
C6A—C61A—C62A—C63A176.43 (19)C6B—C61B—C62B—C63B175.47 (17)
C66A—C61A—C62A—C63A0.9 (3)C66B—C61B—C62B—C63B0.7 (3)
C6A—C61A—C66A—C65A176.76 (18)C6B—C61B—C66B—C65B176.13 (17)
C62A—C61A—C66A—C65A0.5 (3)C62B—C61B—C66B—C65B0.1 (3)
C61A—C62A—C63A—C64A0.7 (3)C61B—C62B—C63B—C64B1.0 (3)
C62A—C63A—C64A—C65A0.2 (4)C62B—C63B—C64B—C65B0.6 (3)
C63A—C64A—C65A—C66A0.1 (3)C63B—C64B—C65B—C66B0.1 (3)
C64A—C65A—C66A—C61A0.0 (3)C64B—C65B—C66B—C61B0.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3, Cg6 and Cg7 are the centroids of phenyl rings C21A–C26A, C31A–C36A, C21B–C26B and C31B–C36B, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4Bi0.88 (2)2.41 (2)3.234 (2)158 (2)
N1B—H1B···O4Aii0.90 (2)2.48 (2)3.315 (2)153 (2)
C2A—H2A···Cg6iii1.002.953.9315 (19)167
C2B—H2B···Cg2iv1.003.003.9733 (19)166
C25B—H25B···Cg3v0.952.783.626 (2)150
C64A—H64A···Cg3ii0.952.783.661 (2)155
C64B—H64B···Cg7i0.952.933.796 (2)153
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z1/2; (v) x+1/2, y+1/2, z+3/2.
 

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