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The asymmetric unit of the title compound, C20H21NO3, contains two crystallographically independent mol­ecules, approximately related by a local twofold axis. These two mol­ecules differ from each other in the orientation of the ethyl group. In both mol­ecules, the piperidone ring adopts a slightly distorted chair conformation, with the phenyl rings and carbethoxy group attached equatorially. The crystal packing is characterized by C—H...π and C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021792/ci6281sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021792/ci6281Isup2.hkl
Contains datablock I

CCDC reference: 226963

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.068
  • wR factor = 0.183
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

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Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.86 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.76 Ratio
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.774 Test value = 0.600 DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.77 e/A   3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.58 Ratio PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1B - H1B ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 14
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

Ethyl 4-oxo-2,6-diphenyl-4-piperidine-3-carboxylate top
Crystal data top
C20H21NO3F(000) = 1376
Mr = 323.39Dx = 1.237 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 20.261 (4) Åθ = 2.5–23°
b = 7.5561 (15) ŵ = 0.08 mm1
c = 23.034 (5) ÅT = 150 K
β = 100.11 (3)°Needles, colourless
V = 3471.6 (12) Å30.44 × 0.30 × 0.24 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
8517 independent reflections
Radiation source: fine-focus sealed tube6735 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 8 pixels mm-1θmax = 28.3°, θmin = 2.0°
ω scansh = 2626
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 109
Tmin = 0.97, Tmax = 0.98l = 2930
31988 measured reflections
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0659P)2 + 3.4759P]
where P = (Fo2 + 2Fc2)/3
8517 reflections(Δ/σ)max = 0.001
463 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.21725 (7)0.2643 (2)0.50455 (7)0.0379 (4)
O2A0.18143 (7)0.0720 (2)0.38108 (7)0.0369 (4)
O3A0.16967 (7)0.3632 (2)0.36209 (7)0.0379 (4)
N1A0.39021 (8)0.1854 (2)0.44272 (7)0.0221 (3)
H1A0.4221 (13)0.120 (3)0.4308 (11)0.033 (6)*
C2A0.32651 (9)0.1455 (2)0.40369 (8)0.0216 (3)
H2A0.31410.02210.40920.026*
C3A0.27153 (9)0.2702 (2)0.41998 (8)0.0223 (4)
H3A0.28170.39140.40930.027*
C4A0.26969 (9)0.2655 (3)0.48597 (8)0.0251 (4)
C5A0.33729 (9)0.2730 (3)0.52525 (8)0.0252 (4)
H5A10.33240.24220.56520.030*
H5A20.35420.39320.52590.030*
C6A0.38857 (9)0.1471 (2)0.50492 (7)0.0205 (3)
H6A0.37440.02440.50880.025*
C7A0.20290 (9)0.2210 (3)0.38592 (8)0.0266 (4)
C8A0.10266 (12)0.3325 (4)0.32770 (13)0.0522 (7)
H8A10.09970.21280.31220.063*
H8A20.09450.41390.29470.063*
C9A0.05198 (14)0.3584 (5)0.36525 (19)0.0790 (12)
H9A10.06340.28850.40040.119*
H9A20.00890.32260.34420.119*
H9A30.05050.48110.37570.119*
C61A0.45676 (9)0.1756 (2)0.54343 (8)0.0212 (3)
C62A0.46760 (10)0.1118 (3)0.60133 (8)0.0277 (4)
H62A0.43410.04940.61500.033*
C63A0.52865 (11)0.1419 (3)0.63864 (9)0.0332 (5)
H63A0.53620.09430.68050.040*
C64A0.57893 (10)0.2361 (3)0.61894 (10)0.0338 (5)
H64A0.62200.25830.64570.041*
C65A0.56878 (10)0.2992 (3)0.56157 (10)0.0338 (5)
H65A0.60280.36120.54800.041*
C66A0.50745 (10)0.2699 (3)0.52389 (9)0.0279 (4)
H66A0.50040.31610.48370.034*
O1B0.27828 (7)0.7924 (2)0.02208 (7)0.0389 (4)
O2B0.32295 (7)0.5959 (2)0.10127 (7)0.0356 (4)
O3B0.33800 (7)0.8913 (2)0.11058 (7)0.0375 (4)
N1B0.11295 (7)0.6945 (2)0.04870 (7)0.0216 (3)
H1B0.0810 (12)0.621 (3)0.0621 (10)0.027 (6)*
C2B0.17907 (9)0.6589 (2)0.08456 (8)0.0215 (3)
H2B0.19270.53750.07730.026*
C21B0.17636 (9)0.6812 (3)0.14961 (8)0.0241 (4)
C22B0.21395 (11)0.5709 (3)0.19125 (9)0.0334 (5)
H22B0.24130.4770.17840.040*
C23B0.21295 (13)0.5927 (4)0.25108 (10)0.0439 (6)
H23B0.23850.5180.27860.053*
C25B0.13694 (13)0.8343 (4)0.22887 (10)0.0408 (5)
H25B0.11130.9210.24130.049*
C24B0.17442 (13)0.7240 (4)0.26981 (10)0.0449 (6)
H24B0.173600.73900.31200.054*
C26B0.13783 (10)0.8143 (3)0.16881 (9)0.0302 (4)
H26B0.11140.8940.14020.036*
C3B0.23051 (9)0.7907 (2)0.06618 (8)0.0222 (4)
H3B0.22000.91000.07850.027*
C4B0.22792 (9)0.7910 (3)0.00057 (8)0.0253 (4)
C5B0.15838 (9)0.7953 (3)0.03677 (8)0.0260 (4)
H5B10.16080.76910.07760.031*
H5B20.13990.91330.03530.031*
C6B0.11151 (9)0.6608 (2)0.01433 (8)0.0217 (3)
H6B0.12780.54070.01940.026*
C61B0.04106 (9)0.6804 (2)0.04962 (8)0.0230 (4)
C62B0.02757 (11)0.6142 (3)0.10716 (9)0.0326 (4)
H62B0.06150.55500.12300.039*
C63B0.03609 (12)0.6355 (3)0.14137 (10)0.0393 (5)
H63B0.04610.58450.18400.047*
C64B0.08570 (10)0.7235 (3)0.11903 (11)0.0364 (5)
H64B0.13140.74060.14430.044*
C65B0.07295 (11)0.7884 (3)0.06216 (11)0.0361 (5)
H65B0.10810.84870.04620.043*
C66B0.00948 (10)0.7674 (3)0.02751 (9)0.0297 (4)
H66B0.00070.81420.01230.036*
C7B0.30141 (9)0.7448 (3)0.09533 (8)0.0261 (4)
C8B0.41108 (12)0.8637 (4)0.12857 (12)0.0482 (6)
H8B10.43460.97320.12400.058*
H8B20.42620.77490.10340.058*
C9B0.42662 (15)0.8052 (5)0.19077 (13)0.0619 (8)
H9B10.41350.89560.21570.093*
H9B20.47390.78380.20150.093*
H9B30.40250.69820.19540.093*
C21A0.33308 (9)0.1748 (3)0.33992 (8)0.0246 (4)
C22A0.29630 (11)0.0710 (3)0.29572 (9)0.0357 (5)
H22A0.26740.0250.30630.043*
C23A0.29985 (13)0.1014 (4)0.23661 (10)0.0473 (6)
H23A0.27290.0280.20560.057*
C24A0.34078 (14)0.2328 (4)0.22134 (10)0.0488 (7)
H24A0.343670.25420.17750.059*
C25A0.37794 (13)0.3358 (4)0.26481 (10)0.0445 (6)
H25A0.40660.4280.25420.053*
C26A0.37407 (11)0.3075 (3)0.32414 (9)0.0324 (4)
H26A0.39880.3770.35290.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0252 (7)0.0568 (10)0.0343 (8)0.0056 (7)0.0120 (6)0.0044 (7)
O2A0.0267 (7)0.0337 (8)0.0492 (9)0.0057 (6)0.0035 (6)0.0016 (7)
O3A0.0269 (7)0.0375 (9)0.0437 (9)0.0016 (6)0.0089 (6)0.0081 (7)
N1A0.0194 (7)0.0277 (8)0.0197 (7)0.0003 (6)0.0048 (6)0.0002 (6)
C2A0.0200 (8)0.0228 (9)0.0217 (8)0.0009 (6)0.0031 (6)0.0000 (6)
C3A0.0192 (8)0.0238 (9)0.0238 (8)0.0004 (7)0.0034 (6)0.0018 (7)
C4A0.0238 (8)0.0256 (9)0.0270 (9)0.0036 (7)0.0074 (7)0.0010 (7)
C5A0.0242 (9)0.0305 (10)0.0214 (8)0.0030 (7)0.0057 (7)0.0015 (7)
C6A0.0203 (8)0.0222 (8)0.0193 (8)0.0003 (6)0.0041 (6)0.0000 (6)
C7A0.0216 (8)0.0312 (10)0.0275 (9)0.0008 (7)0.0058 (7)0.0027 (7)
C8A0.0349 (12)0.0525 (16)0.0605 (17)0.0033 (11)0.0153 (11)0.0103 (13)
C9A0.0321 (13)0.078 (2)0.123 (3)0.0002 (14)0.0011 (16)0.039 (2)
C61A0.0200 (8)0.0194 (8)0.0240 (8)0.0007 (6)0.0031 (6)0.0028 (6)
C62A0.0266 (9)0.0315 (10)0.0244 (9)0.0038 (8)0.0026 (7)0.0014 (7)
C63A0.0352 (11)0.0344 (11)0.0265 (10)0.0009 (9)0.0039 (8)0.0004 (8)
C64A0.0270 (9)0.0300 (11)0.0405 (11)0.0004 (8)0.0049 (8)0.0061 (9)
C65A0.0235 (9)0.0333 (11)0.0438 (12)0.0068 (8)0.0039 (8)0.0007 (9)
C66A0.0249 (9)0.0296 (10)0.0292 (9)0.0020 (7)0.0045 (7)0.0014 (8)
O1B0.0263 (7)0.0597 (11)0.0332 (8)0.0070 (7)0.0120 (6)0.0046 (7)
O2B0.0231 (7)0.0312 (8)0.0514 (9)0.0038 (6)0.0033 (6)0.0046 (7)
O3B0.0285 (7)0.0298 (8)0.0485 (9)0.0013 (6)0.0091 (6)0.0011 (7)
N1B0.0183 (7)0.0268 (8)0.0200 (7)0.0006 (6)0.0038 (5)0.0012 (6)
C2B0.0197 (8)0.0213 (8)0.0229 (8)0.0014 (6)0.0027 (6)0.0011 (6)
C21B0.0236 (8)0.0254 (9)0.0230 (8)0.0036 (7)0.0028 (7)0.0008 (7)
C22B0.0292 (10)0.0386 (12)0.0306 (10)0.0014 (9)0.0006 (8)0.0082 (9)
C23B0.0437 (12)0.0587 (16)0.0267 (10)0.0088 (11)0.0013 (9)0.0137 (10)
C25B0.0454 (13)0.0475 (14)0.0322 (11)0.0079 (11)0.0141 (10)0.0109 (10)
C24B0.0526 (14)0.0594 (16)0.0229 (10)0.0187 (12)0.0074 (9)0.0002 (10)
C26B0.0322 (10)0.0309 (10)0.0278 (10)0.0001 (8)0.0066 (8)0.0005 (8)
C3B0.0199 (8)0.0226 (9)0.0239 (8)0.0003 (7)0.0032 (6)0.0005 (7)
C4B0.0225 (8)0.0268 (9)0.0273 (9)0.0029 (7)0.0059 (7)0.0004 (7)
C5B0.0243 (9)0.0326 (10)0.0218 (8)0.0021 (8)0.0058 (7)0.0019 (7)
C6B0.0202 (8)0.0234 (9)0.0217 (8)0.0016 (7)0.0039 (6)0.0008 (6)
C61B0.0225 (8)0.0213 (9)0.0246 (9)0.0005 (7)0.0026 (7)0.0009 (7)
C62B0.0315 (10)0.0356 (11)0.0291 (10)0.0036 (9)0.0005 (8)0.0064 (8)
C63B0.0391 (12)0.0386 (12)0.0351 (11)0.0002 (10)0.0076 (9)0.0053 (9)
C64B0.0254 (9)0.0323 (11)0.0462 (12)0.0011 (8)0.0082 (9)0.0050 (9)
C65B0.0248 (9)0.0374 (12)0.0455 (12)0.0041 (9)0.0047 (9)0.0018 (9)
C66B0.0243 (9)0.0335 (11)0.0316 (10)0.0025 (8)0.0056 (8)0.0003 (8)
C7B0.0205 (8)0.0305 (10)0.0272 (9)0.0001 (7)0.0036 (7)0.0024 (7)
C8B0.0337 (12)0.0439 (14)0.0615 (16)0.0062 (10)0.0068 (11)0.0055 (12)
C9B0.0525 (16)0.075 (2)0.0520 (16)0.0129 (15)0.0085 (13)0.0038 (15)
C21A0.0228 (8)0.0282 (9)0.0224 (8)0.0054 (7)0.0032 (7)0.0004 (7)
C22A0.0308 (10)0.0448 (13)0.0304 (10)0.0010 (9)0.0026 (8)0.0100 (9)
C23A0.0428 (13)0.0715 (18)0.0252 (10)0.0105 (13)0.0005 (9)0.0131 (11)
C24A0.0526 (14)0.0718 (19)0.0226 (10)0.0230 (13)0.0081 (10)0.0053 (11)
C25A0.0502 (14)0.0503 (15)0.0358 (12)0.0093 (12)0.0159 (10)0.0165 (11)
C26A0.0386 (11)0.0320 (11)0.0270 (10)0.0010 (9)0.0069 (8)0.0047 (8)
Geometric parameters (Å, º) top
O1A—C4A1.213 (2)C21B—C26B1.392 (3)
O2A—C7A1.205 (3)C22B—C23B1.391 (3)
O3A—C7A1.334 (2)C22B—H22B0.98
O3A—C8A1.465 (3)C23B—C24B1.378 (4)
N1A—C6A1.468 (2)C23B—H23B0.94
N1A—C2A1.469 (2)C25B—C24B1.382 (4)
N1A—H1A0.90 (3)C25B—C26B1.395 (3)
C2A—C21A1.514 (2)C25B—H25B0.91
C2A—C3A1.554 (2)C24B—H24B0.98
C2A—H2A0.98C26B—H26B0.98
C3A—C7A1.518 (2)C3B—C7B1.515 (2)
C3A—C4A1.527 (3)C3B—C4B1.529 (3)
C3A—H3A0.98C3B—H3B0.98
C4A—C5A1.504 (3)C4B—C5B1.506 (3)
C5A—C6A1.541 (2)C5B—C6B1.541 (3)
C5A—H5A10.97C5B—H5B10.97
C5A—H5A20.97C5B—H5B20.97
C6A—C61A1.520 (2)C6B—C61B1.521 (2)
C6A—H6A0.98C6B—H6B0.98
C8A—C9A1.467 (5)C61B—C66B1.387 (3)
C8A—H8A10.97C61B—C62B1.398 (3)
C8A—H8A20.97C62B—C63B1.398 (3)
C9A—H9A10.96C62B—H62B0.95
C9A—H9A20.96C63B—C64B1.378 (3)
C9A—H9A30.96C63B—H63B1.04
C61A—C66A1.388 (3)C64B—C65B1.380 (3)
C61A—C62A1.399 (3)C64B—H64B1.01
C62A—C63A1.395 (3)C65B—C66B1.398 (3)
C62A—H62A0.93C65B—H65B0.97
C63A—C64A1.383 (3)C66B—H66B0.97
C63A—H63A1.02C8B—C9B1.479 (4)
C64A—C65A1.386 (3)C8B—H8B10.97
C64A—H64A0.99C8B—H8B20.97
C65A—C66A1.403 (3)C9B—H9B10.96
C65A—H65A0.93C9B—H9B20.96
C66A—H66A0.98C9B—H9B30.96
O1B—C4B1.210 (2)C21A—C26A1.390 (3)
O2B—C7B1.206 (3)C21A—C22A1.393 (3)
O3B—C7B1.344 (2)C22A—C23A1.395 (3)
O3B—C8B1.481 (3)C22A—H22A0.99
N1B—C6B1.469 (2)C23A—C24A1.378 (4)
N1B—C2B1.470 (2)C23A—H23A0.99
N1B—H1B0.95 (2)C24A—C25A1.383 (4)
C2B—C21B1.518 (3)C24A—H24A1.03
C2B—C3B1.553 (2)C25A—C26A1.399 (3)
C2B—H2B0.98C25A—H25A0.96
C21B—C22B1.392 (3)C26A—H26A0.92
C7A—O3A—C8A116.57 (18)C22B—C23B—H23B119.9
C6A—N1A—C2A112.88 (14)C24B—C25B—C26B120.7 (2)
C6A—N1A—H1A109.3 (16)C24B—C25B—H25B119.7
C2A—N1A—H1A107.6 (16)C26B—C25B—H25B119.7
N1A—C2A—C21A110.25 (15)C23B—C24B—C25B119.6 (2)
N1A—C2A—C3A108.54 (14)C23B—C24B—H24B120.2
C21A—C2A—C3A109.55 (14)C25B—C24B—H24B120.2
N1A—C2A—H2A109.5C21B—C26B—C25B119.9 (2)
C21A—C2A—H2A109.5C21B—C26B—H26B120.0
C3A—C2A—H2A109.5C25B—C26B—H26B120.0
C7A—C3A—C4A109.17 (15)C7B—C3B—C4B107.96 (15)
C7A—C3A—C2A110.93 (15)C7B—C3B—C2B111.20 (15)
C4A—C3A—C2A111.71 (14)C4B—C3B—C2B111.64 (14)
C7A—C3A—H3A108.3C7B—C3B—H3B108.7
C4A—C3A—H3A108.3C4B—C3B—H3B108.7
C2A—C3A—H3A108.3C2B—C3B—H3B108.7
O1A—C4A—C5A123.33 (18)O1B—C4B—C5B123.17 (18)
O1A—C4A—C3A121.81 (17)O1B—C4B—C3B121.95 (17)
C5A—C4A—C3A114.77 (15)C5B—C4B—C3B114.85 (15)
C4A—C5A—C6A112.65 (15)C4B—C5B—C6B111.81 (15)
C4A—C5A—H5A1109.1C4B—C5B—H5B1109.3
C6A—C5A—H5A1109.1C6B—C5B—H5B1109.3
C4A—C5A—H5A2109.1C4B—C5B—H5B2109.3
C6A—C5A—H5A2109.1C6B—C5B—H5B2109.3
H5A1—C5A—H5A2107.8H5B1—C5B—H5B2107.9
N1A—C6A—C61A111.56 (14)N1B—C6B—C61B111.42 (15)
N1A—C6A—C5A107.88 (14)N1B—C6B—C5B108.10 (15)
C61A—C6A—C5A109.11 (14)C61B—C6B—C5B109.42 (15)
N1A—C6A—H6A109.4N1B—C6B—H6B109.3
C61A—C6A—H6A109.4C61B—C6B—H6B109.3
C5A—C6A—H6A109.4C5B—C6B—H6B109.3
O2A—C7A—O3A124.53 (18)C66B—C61B—C62B118.93 (18)
O2A—C7A—C3A124.04 (18)C66B—C61B—C6B122.29 (17)
O3A—C7A—C3A111.43 (17)C62B—C61B—C6B118.74 (17)
O3A—C8A—C9A109.8 (2)C63B—C62B—C61B120.0 (2)
O3A—C8A—H8A1109.7C63B—C62B—H62B120.0
C9A—C8A—H8A1109.7C61B—C62B—H62B120.0
O3A—C8A—H8A2109.7C64B—C63B—C62B120.4 (2)
C9A—C8A—H8A2109.7C64B—C63B—H63B119.8
H8A1—C8A—H8A2108.2C62B—C63B—H63B119.8
C8A—C9A—H9A1109.5C63B—C64B—C65B119.92 (19)
C8A—C9A—H9A2109.5C63B—C64B—H64B120.0
H9A1—C9A—H9A2109.5C65B—C64B—H64B120.0
C8A—C9A—H9A3109.5C64B—C65B—C66B120.1 (2)
H9A1—C9A—H9A3109.5C64B—C65B—H65B120.0
H9A2—C9A—H9A3109.5C66B—C65B—H65B120.0
C66A—C61A—C62A118.99 (17)C61B—C66B—C65B120.6 (2)
C66A—C61A—C6A122.12 (16)C61B—C66B—H66B119.7
C62A—C61A—C6A118.82 (16)C65B—C66B—H66B119.7
C63A—C62A—C61A120.33 (19)O2B—C7B—O3B124.52 (17)
C63A—C62A—H62A119.8O2B—C7B—C3B124.04 (17)
C61A—C62A—H62A119.8O3B—C7B—C3B111.34 (16)
C64A—C63A—C62A120.41 (19)O3B—C8B—C9B110.2 (2)
C64A—C63A—H63A119.8O3B—C8B—H8B1109.6
C62A—C63A—H63A119.8C9B—C8B—H8B1109.6
C63A—C64A—C65A119.69 (19)O3B—C8B—H8B2109.6
C63A—C64A—H64A120.2C9B—C8B—H8B2109.6
C65A—C64A—H64A120.2H8B1—C8B—H8B2108.1
C64A—C65A—C66A120.2 (2)C8B—C9B—H9B1109.5
C64A—C65A—H65A119.9C8B—C9B—H9B2109.5
C66A—C65A—H65A119.9H9B1—C9B—H9B2109.5
C61A—C66A—C65A120.38 (19)C8B—C9B—H9B3109.5
C61A—C66A—H66A119.8H9B1—C9B—H9B3109.5
C65A—C66A—H66A119.8H9B2—C9B—H9B3109.5
C7B—O3B—C8B115.84 (17)C26A—C21A—C22A118.83 (19)
C6B—N1B—C2B112.43 (14)C26A—C21A—C2A121.14 (17)
C6B—N1B—H1B109.0 (14)C22A—C21A—C2A120.00 (18)
C2B—N1B—H1B108.4 (14)C21A—C22A—C23A120.6 (2)
N1B—C2B—C21B110.30 (15)C21A—C22A—H22A119.7
N1B—C2B—C3B108.56 (14)C23A—C22A—H22A119.7
C21B—C2B—C3B109.87 (14)C24A—C23A—C22A120.3 (2)
N1B—C2B—H2B109.4C24A—C23A—H23A119.9
C21B—C2B—H2B109.4C22A—C23A—H23A119.9
C3B—C2B—H2B109.4C23A—C24A—C25A119.8 (2)
C22B—C21B—C26B118.89 (19)C23A—C24A—H24A120.1
C22B—C21B—C2B120.21 (18)C25A—C24A—H24A120.1
C26B—C21B—C2B120.88 (17)C24A—C25A—C26A120.3 (2)
C23B—C22B—C21B120.7 (2)C24A—C25A—H25A119.9
C23B—C22B—H22B119.7C26A—C25A—H25A119.9
C21B—C22B—H22B119.7C21A—C26A—C25A120.3 (2)
C24B—C23B—C22B120.2 (2)C21A—C26A—H26A119.9
C24B—C23B—H23B119.9C25A—C26A—H26A119.9
C6A—N1A—C2A—C21A175.78 (15)C2B—C21B—C26B—C25B178.95 (19)
C6A—N1A—C2A—C3A64.23 (19)C24B—C25B—C26B—C21B0.5 (3)
N1A—C2A—C3A—C7A173.45 (14)N1B—C2B—C3B—C7B172.06 (15)
C21A—C2A—C3A—C7A66.11 (19)C21B—C2B—C3B—C7B67.25 (19)
N1A—C2A—C3A—C4A51.40 (19)N1B—C2B—C3B—C4B51.41 (19)
C21A—C2A—C3A—C4A171.83 (15)C21B—C2B—C3B—C4B172.10 (15)
C7A—C3A—C4A—O1A15.9 (3)C7B—C3B—C4B—O1B14.4 (3)
C2A—C3A—C4A—O1A138.9 (2)C2B—C3B—C4B—O1B137.0 (2)
C7A—C3A—C4A—C5A167.49 (16)C7B—C3B—C4B—C5B167.43 (16)
C2A—C3A—C4A—C5A44.4 (2)C2B—C3B—C4B—C5B44.9 (2)
O1A—C4A—C5A—C6A137.7 (2)O1B—C4B—C5B—C6B135.4 (2)
C3A—C4A—C5A—C6A45.7 (2)C3B—C4B—C5B—C6B46.5 (2)
C2A—N1A—C6A—C61A175.38 (15)C2B—N1B—C6B—C61B174.20 (15)
C2A—N1A—C6A—C5A64.79 (19)C2B—N1B—C6B—C5B65.54 (19)
C4A—C5A—C6A—N1A53.4 (2)C4B—C5B—C6B—N1B54.4 (2)
C4A—C5A—C6A—C61A174.78 (15)C4B—C5B—C6B—C61B175.96 (16)
C8A—O3A—C7A—O2A0.2 (3)N1B—C6B—C61B—C66B17.1 (3)
C8A—O3A—C7A—C3A179.67 (19)C5B—C6B—C61B—C66B102.4 (2)
C4A—C3A—C7A—O2A76.3 (2)N1B—C6B—C61B—C62B165.42 (18)
C2A—C3A—C7A—O2A47.2 (3)C5B—C6B—C61B—C62B75.1 (2)
C4A—C3A—C7A—O3A103.79 (18)C66B—C61B—C62B—C63B0.3 (3)
C2A—C3A—C7A—O3A132.69 (17)C6B—C61B—C62B—C63B177.9 (2)
C7A—O3A—C8A—C9A94.7 (3)C61B—C62B—C63B—C64B0.8 (4)
N1A—C6A—C61A—C66A15.8 (2)C62B—C63B—C64B—C65B1.2 (4)
C5A—C6A—C61A—C66A103.3 (2)C63B—C64B—C65B—C66B1.0 (4)
N1A—C6A—C61A—C62A167.30 (17)C62B—C61B—C66B—C65B0.1 (3)
C5A—C6A—C61A—C62A73.6 (2)C6B—C61B—C66B—C65B177.60 (19)
C66A—C61A—C62A—C63A0.4 (3)C64B—C65B—C66B—C61B0.5 (3)
C6A—C61A—C62A—C63A177.39 (18)C8B—O3B—C7B—O2B8.0 (3)
C61A—C62A—C63A—C64A0.5 (3)C8B—O3B—C7B—C3B168.45 (18)
C62A—C63A—C64A—C65A0.7 (3)C4B—C3B—C7B—O2B82.0 (2)
C63A—C64A—C65A—C66A0.9 (3)C2B—C3B—C7B—O2B40.8 (3)
C62A—C61A—C66A—C65A0.6 (3)C4B—C3B—C7B—O3B94.48 (19)
C6A—C61A—C66A—C65A177.49 (18)C2B—C3B—C7B—O3B142.73 (17)
C64A—C65A—C66A—C61A0.9 (3)C7B—O3B—C8B—C9B81.2 (3)
C6B—N1B—C2B—C21B175.40 (15)N1A—C2A—C21A—C26A33.7 (2)
C6B—N1B—C2B—C3B64.17 (19)C3A—C2A—C21A—C26A85.7 (2)
N1B—C2B—C21B—C22B144.10 (18)N1A—C2A—C21A—C22A148.08 (18)
C3B—C2B—C21B—C22B96.3 (2)C3A—C2A—C21A—C22A92.5 (2)
N1B—C2B—C21B—C26B37.5 (2)C26A—C21A—C22A—C23A0.9 (3)
C3B—C2B—C21B—C26B82.1 (2)C2A—C21A—C22A—C23A177.4 (2)
C26B—C21B—C22B—C23B0.2 (3)C21A—C22A—C23A—C24A1.1 (4)
C2B—C21B—C22B—C23B178.63 (19)C22A—C23A—C24A—C25A0.6 (4)
C21B—C22B—C23B—C24B0.1 (3)C23A—C24A—C25A—C26A0.1 (4)
C22B—C23B—C24B—C25B0.2 (4)C22A—C21A—C26A—C25A0.2 (3)
C26B—C25B—C24B—C23B0.1 (4)C2A—C21A—C26A—C25A178.10 (19)
C22B—C21B—C26B—C25B0.6 (3)C24A—C25A—C26A—C21A0.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O2Bi0.982.693.332 (2)124
C6B—H6B···O2Aii0.982.833.479 (2)124
C62A—H62A···O2Bi0.932.483.324 (3)153
C62B—H62B···O2Aii0.952.603.474 (3)154
C65A—H65A···O1Biii0.932.633.380 (3)138
C65B—H65B···O1Aiv0.972.643.421 (3)138
N1A—H1A···Cg3v0.90 (3)2.78 (2)3.586 (2)151 (2)
N1B—H1B···Cg4vi0.95 (2)2.80 (2)3.677 (2)155 (2)
C9A—H9A3···Cg4vii0.963.043.911 (4)151
C8B—H8B1···Cg3viii0.973.214.159 (2)167
C23A—H23A···Cg2ix0.993.173.906 (3)133
C23B—H23B···Cg10.943.103.848 (3)139
C63B—H63B···Cg2vi1.043.373.928 (3)115
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x+1, y1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x+1, y, z+1; (vi) x, y+1, z; (vii) x, y+3/2, z+1/2; (viii) x, y+3/2, z1/2; (ix) x, y1, z.
 

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