2-(2,6-Diphenyl­piperidin-1-yl)ethanol

The title compound, C₁₉H₂₃NO, crystallizes with two mol­ecules in the asymmetric unit. The piperidine ring adopts a chair conformation in both mol­ecules. Intra­molecular O—H...N and C—H...π inter­actions are observed in only one mol­ecule in the asymmetric unit. The crystal packing is stabilized by O—H...O inter­molecular inter­actions, generating R₄⁴(8) rings.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.173
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1B    -   C7B     ..       8.97 su

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.66
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6B    -   C7B     ..       6.89 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         22

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2-(2,6-diphenylpiperidine)ethan-1-ol

Crystal data

C19H23NO	Z = 4
Mr = 281.38	F(000) = 608
Triclinic, P1	Dx = 1.152 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.7863 (9) Å	Cell parameters from 3675 reflections
b = 12.2482 (9) Å	θ = 1.7–25.0°
c = 12.8201 (10) Å	µ = 0.07 mm^−1
α = 95.077 (1)°	T = 293 K
β = 107.637 (1)°	Block, colourless
γ = 109.768 (1)°	0.26 × 0.24 × 0.21 mm
V = 1621.7 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5335 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 28.0°, θmin = 1.7°
ω scans	h = −14→14
18837 measured reflections	k = −16→16
7414 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0901P)^2 + 0.2212P] where P = (Fo^2 + 2Fc^2)/3
7414 reflections	(Δ/σ)max < 0.001
381 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.53968 (14)	0.67168 (14)	0.30040 (13)	0.0536 (4)
H1A	0.5322	0.7413	0.3369	0.064*
C2A	0.55398 (17)	0.59068 (18)	0.38367 (15)	0.0717 (5)
H2A1	0.4799	0.5682	0.4072	0.086*
H2A2	0.5557	0.5188	0.3469	0.086*
C3A	0.67537 (18)	0.6507 (2)	0.48527 (16)	0.0793 (6)
H3A1	0.6850	0.5954	0.5337	0.095*
H3A2	0.6703	0.7178	0.5272	0.095*
C4A	0.78998 (17)	0.69280 (18)	0.44803 (14)	0.0674 (5)
H4A1	0.7994	0.6247	0.4126	0.081*
H4A2	0.8676	0.7352	0.5130	0.081*
C5A	0.77432 (14)	0.77421 (14)	0.36576 (12)	0.0508 (3)
H5A	0.7680	0.8438	0.4037	0.061*
C6A	0.63983 (14)	0.78453 (12)	0.18240 (11)	0.0477 (3)
H6A1	0.5686	0.7347	0.1153	0.057*
H6A2	0.7173	0.8080	0.1637	0.057*
C7A	0.61656 (19)	0.89604 (14)	0.21343 (14)	0.0646 (4)
H7A1	0.5340	0.8734	0.2236	0.077*
H7A2	0.6830	0.9437	0.2840	0.077*
C8A	0.41760 (15)	0.60665 (14)	0.19859 (14)	0.0583 (4)
C9A	0.31196 (17)	0.6371 (2)	0.18112 (16)	0.0801 (6)
H9A	0.3161	0.7000	0.2304	0.096*
C10A	0.1997 (2)	0.5743 (3)	0.0904 (2)	0.1061 (9)
H10A	0.1285	0.5949	0.0795	0.127*
C11A	0.1923 (2)	0.4824 (3)	0.0168 (2)	0.1045 (9)
H11A	0.1165	0.4407	−0.0438	0.125*
C12A	0.2955 (2)	0.45208 (19)	0.03224 (19)	0.0926 (7)
H12A	0.2906	0.3896	−0.0181	0.111*
C13A	0.4084 (2)	0.51382 (16)	0.12275 (17)	0.0765 (5)
H13A	0.4790	0.4925	0.1326	0.092*
C14A	0.88998 (14)	0.81642 (15)	0.33019 (12)	0.0538 (4)
C15A	0.96836 (18)	0.93601 (18)	0.35584 (16)	0.0727 (5)
H15A	0.9479	0.9905	0.3939	0.087*
C16A	1.0753 (2)	0.9756 (2)	0.3263 (2)	0.0966 (7)
H16A	1.1267	1.0562	0.3447	0.116*
C17A	1.1068 (2)	0.8979 (3)	0.2704 (2)	0.1008 (8)
H17A	1.1795	0.9251	0.2505	0.121*
C18A	1.0309 (2)	0.7786 (3)	0.24315 (17)	0.0923 (7)
H18A	1.0522	0.7253	0.2044	0.111*
C19A	0.92242 (17)	0.73764 (18)	0.27336 (15)	0.0693 (5)
H19A	0.8717	0.6569	0.2552	0.083*
N1A	0.65401 (11)	0.71238 (10)	0.26765 (9)	0.0458 (3)
O1A	0.61727 (13)	0.96354 (10)	0.13184 (10)	0.0719 (3)
H1A1	0.5587	0.9246	0.0729	0.108*
C1B	0.51760 (14)	0.21463 (14)	0.31952 (13)	0.0552 (4)
H1B	0.5194	0.2899	0.3546	0.066*
C2B	0.52539 (17)	0.13761 (17)	0.40625 (15)	0.0697 (5)
H2B1	0.4532	0.1248	0.4316	0.084*
H2B2	0.5187	0.0609	0.3717	0.084*
C3B	0.6501 (2)	0.1940 (2)	0.50604 (15)	0.0796 (5)
H3B1	0.6544	0.1409	0.5577	0.096*
H3B2	0.6543	0.2675	0.5452	0.096*
C4B	0.76184 (17)	0.21849 (18)	0.46428 (14)	0.0671 (4)
H4B1	0.7612	0.1438	0.4312	0.080*
H4B2	0.8424	0.2581	0.5271	0.080*
C5B	0.75394 (14)	0.29563 (14)	0.37775 (12)	0.0513 (3)
H5B	0.7593	0.3720	0.4139	0.062*
C6B	0.62284 (14)	0.31875 (13)	0.20022 (13)	0.0527 (4)
H6B1	0.6782	0.4001	0.2388	0.063*
H6B2	0.5351	0.3149	0.1705	0.063*
C7B	0.66231 (16)	0.28634 (16)	0.10337 (14)	0.0640 (4)
H7B1	0.6436	0.3332	0.0483	0.077*
H7B2	0.7546	0.3061	0.1307	0.077*
C8B	0.39271 (14)	0.15611 (14)	0.22030 (14)	0.0559 (4)
C9B	0.30356 (16)	0.20855 (17)	0.19315 (16)	0.0670 (4)
H9B	0.3180	0.2789	0.2388	0.080*
C10B	0.19288 (17)	0.1571 (2)	0.09855 (19)	0.0815 (6)
H10B	0.1338	0.1934	0.0810	0.098*
C11B	0.16996 (17)	0.0534 (2)	0.03072 (18)	0.0828 (6)
H11B	0.0966	0.0202	−0.0337	0.099*
C12B	0.25594 (17)	−0.00136 (18)	0.05845 (17)	0.0770 (5)
H12B	0.2394	−0.0731	0.0138	0.092*
C13B	0.36639 (16)	0.04946 (15)	0.15195 (16)	0.0646 (4)
H13B	0.4242	0.0119	0.1696	0.077*
C14B	0.86707 (13)	0.31918 (13)	0.33777 (11)	0.0489 (3)
C15B	0.95472 (15)	0.43364 (14)	0.35296 (13)	0.0591 (4)
H15B	0.9453	0.4972	0.3897	0.071*
C16B	1.05586 (17)	0.45457 (17)	0.31418 (16)	0.0713 (5)
H16B	1.1138	0.5319	0.3250	0.086*
C17B	1.07130 (17)	0.36220 (19)	0.25997 (16)	0.0712 (5)
H17B	1.1390	0.3765	0.2333	0.085*
C18B	0.98581 (17)	0.24794 (17)	0.24530 (15)	0.0667 (4)
H18B	0.9962	0.1848	0.2089	0.080*
C19B	0.88481 (15)	0.22631 (14)	0.28419 (13)	0.0561 (4)
H19B	0.8281	0.1486	0.2743	0.067*
N1B	0.62989 (11)	0.24143 (10)	0.28200 (10)	0.0470 (3)
O1B	0.59882 (12)	0.16612 (10)	0.05199 (9)	0.0678 (3)
H1B1	0.6115	0.1260	0.0989	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0517 (8)	0.0559 (8)	0.0533 (8)	0.0199 (7)	0.0181 (7)	0.0174 (7)
C2A	0.0658 (10)	0.0822 (12)	0.0675 (10)	0.0220 (9)	0.0254 (9)	0.0378 (9)
C3A	0.0737 (12)	0.1049 (15)	0.0609 (10)	0.0303 (11)	0.0233 (9)	0.0441 (10)
C4A	0.0625 (10)	0.0868 (12)	0.0533 (9)	0.0316 (9)	0.0135 (7)	0.0306 (8)
C5A	0.0504 (8)	0.0554 (8)	0.0428 (7)	0.0209 (7)	0.0105 (6)	0.0115 (6)
C6A	0.0489 (7)	0.0471 (7)	0.0426 (7)	0.0175 (6)	0.0102 (6)	0.0134 (6)
C7A	0.0845 (12)	0.0508 (9)	0.0606 (9)	0.0303 (8)	0.0227 (8)	0.0161 (7)
C8A	0.0505 (8)	0.0589 (9)	0.0589 (9)	0.0125 (7)	0.0175 (7)	0.0224 (7)
C9A	0.0529 (10)	0.1239 (17)	0.0643 (11)	0.0315 (10)	0.0257 (8)	0.0168 (11)
C10A	0.0481 (10)	0.180 (3)	0.0809 (14)	0.0328 (14)	0.0239 (10)	0.0225 (17)
C11A	0.0588 (12)	0.130 (2)	0.0765 (14)	−0.0079 (13)	0.0109 (10)	0.0155 (14)
C12A	0.0949 (17)	0.0613 (11)	0.0809 (13)	0.0052 (11)	0.0064 (12)	0.0065 (10)
C13A	0.0794 (12)	0.0522 (9)	0.0787 (12)	0.0202 (9)	0.0082 (10)	0.0129 (9)
C14A	0.0471 (8)	0.0635 (9)	0.0426 (7)	0.0186 (7)	0.0069 (6)	0.0142 (6)
C15A	0.0635 (10)	0.0714 (11)	0.0656 (10)	0.0134 (9)	0.0125 (8)	0.0176 (9)
C16A	0.0679 (13)	0.1024 (17)	0.0885 (15)	0.0018 (12)	0.0175 (11)	0.0323 (13)
C17A	0.0548 (11)	0.152 (3)	0.0774 (14)	0.0147 (14)	0.0225 (10)	0.0419 (15)
C18A	0.0705 (13)	0.145 (2)	0.0657 (12)	0.0483 (15)	0.0243 (10)	0.0147 (13)
C19A	0.0565 (9)	0.0854 (12)	0.0609 (10)	0.0273 (9)	0.0152 (8)	0.0113 (9)
N1A	0.0459 (6)	0.0461 (6)	0.0439 (6)	0.0185 (5)	0.0117 (5)	0.0150 (5)
O1A	0.0859 (9)	0.0539 (7)	0.0686 (7)	0.0275 (6)	0.0143 (6)	0.0219 (6)
C1B	0.0523 (8)	0.0547 (8)	0.0624 (9)	0.0205 (7)	0.0267 (7)	0.0090 (7)
C2B	0.0678 (11)	0.0786 (12)	0.0704 (11)	0.0232 (9)	0.0377 (9)	0.0255 (9)
C3B	0.0879 (13)	0.0988 (15)	0.0573 (10)	0.0320 (11)	0.0339 (10)	0.0284 (10)
C4B	0.0656 (10)	0.0839 (12)	0.0496 (9)	0.0273 (9)	0.0172 (8)	0.0212 (8)
C5B	0.0506 (8)	0.0521 (8)	0.0470 (7)	0.0185 (6)	0.0140 (6)	0.0059 (6)
C6B	0.0461 (8)	0.0510 (8)	0.0614 (9)	0.0201 (6)	0.0162 (7)	0.0179 (7)
C7B	0.0606 (9)	0.0735 (11)	0.0574 (9)	0.0255 (8)	0.0170 (8)	0.0281 (8)
C8B	0.0463 (8)	0.0584 (9)	0.0679 (9)	0.0174 (7)	0.0300 (7)	0.0140 (7)
C9B	0.0539 (9)	0.0712 (11)	0.0834 (12)	0.0257 (8)	0.0333 (9)	0.0138 (9)
C10B	0.0485 (10)	0.1060 (16)	0.0965 (14)	0.0332 (10)	0.0296 (10)	0.0252 (13)
C11B	0.0453 (9)	0.1095 (16)	0.0794 (12)	0.0152 (10)	0.0235 (9)	0.0049 (12)
C12B	0.0540 (10)	0.0786 (12)	0.0851 (12)	0.0072 (9)	0.0336 (9)	−0.0047 (10)
C13B	0.0512 (9)	0.0616 (10)	0.0813 (11)	0.0172 (7)	0.0309 (8)	0.0084 (8)
C14B	0.0436 (7)	0.0543 (8)	0.0424 (7)	0.0183 (6)	0.0079 (6)	0.0087 (6)
C15B	0.0566 (9)	0.0537 (9)	0.0560 (9)	0.0153 (7)	0.0138 (7)	0.0045 (7)
C16B	0.0558 (9)	0.0672 (11)	0.0746 (11)	0.0071 (8)	0.0198 (8)	0.0148 (9)
C17B	0.0547 (9)	0.0912 (14)	0.0712 (11)	0.0279 (9)	0.0262 (8)	0.0215 (10)
C18B	0.0649 (10)	0.0768 (12)	0.0656 (10)	0.0364 (9)	0.0233 (8)	0.0122 (9)
C19B	0.0514 (8)	0.0545 (9)	0.0580 (9)	0.0207 (7)	0.0140 (7)	0.0100 (7)
N1B	0.0439 (6)	0.0480 (6)	0.0498 (6)	0.0170 (5)	0.0175 (5)	0.0126 (5)
O1B	0.0859 (8)	0.0664 (7)	0.0482 (6)	0.0322 (6)	0.0153 (6)	0.0163 (5)

Geometric parameters (Å, º)

C1A—N1A	1.472 (2)	C1B—N1B	1.487 (2)
C1A—C8A	1.520 (2)	C1B—C8B	1.513 (2)
C1A—C2A	1.531 (2)	C1B—C2B	1.522 (2)
C1A—H1A	0.9800	C1B—H1B	0.9800
C2A—C3A	1.508 (3)	C2B—C3B	1.514 (3)
C2A—H2A1	0.9700	C2B—H2B1	0.9700
C2A—H2A2	0.9700	C2B—H2B2	0.9700
C3A—C4A	1.510 (3)	C3B—C4B	1.516 (3)
C3A—H3A1	0.9700	C3B—H3B1	0.9700
C3A—H3A2	0.9700	C3B—H3B2	0.9700
C4A—C5A	1.528 (2)	C4B—C5B	1.521 (2)
C4A—H4A1	0.9700	C4B—H4B1	0.9700
C4A—H4A2	0.9700	C4B—H4B2	0.9700
C5A—N1A	1.480 (2)	C5B—N1B	1.482 (2)
C5A—C14A	1.508 (2)	C5B—C14B	1.518 (2)
C5A—H5A	0.9800	C5B—H5B	0.9800
C6A—N1A	1.471 (2)	C6B—N1B	1.476 (2)
C6A—C7A	1.524 (2)	C6B—C7B	1.518 (2)
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
C7A—O1A	1.390 (2)	C7B—O1B	1.395 (2)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
C8A—C9A	1.378 (3)	C8B—C9B	1.383 (2)
C8A—C13A	1.381 (3)	C8B—C13B	1.389 (2)
C9A—C10A	1.385 (3)	C9B—C10B	1.385 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.363 (4)	C10B—C11B	1.369 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.353 (4)	C11B—C12B	1.374 (3)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.385 (3)	C12B—C13B	1.376 (3)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C19A	1.379 (2)	C14B—C19B	1.385 (2)
C14A—C15A	1.387 (3)	C14B—C15B	1.386 (2)
C15A—C16A	1.370 (3)	C15B—C16B	1.382 (2)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.354 (4)	C16B—C17B	1.369 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.376 (4)	C17B—C18B	1.376 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.392 (3)	C18B—C19B	1.380 (2)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—H19A	0.9300	C19B—H19B	0.9300
O1A—H1A1	0.8200	O1B—H1B1	0.8200
N1A—C1A—C8A	111.07 (12)	N1B—C1B—C8B	110.44 (12)
N1A—C1A—C2A	110.53 (12)	N1B—C1B—C2B	111.13 (12)
C8A—C1A—C2A	109.85 (13)	C8B—C1B—C2B	110.99 (13)
N1A—C1A—H1A	108.4	N1B—C1B—H1B	108.0
C8A—C1A—H1A	108.4	C8B—C1B—H1B	108.0
C2A—C1A—H1A	108.4	C2B—C1B—H1B	108.0
C3A—C2A—C1A	111.76 (15)	C3B—C2B—C1B	111.96 (14)
C3A—C2A—H2A1	109.3	C3B—C2B—H2B1	109.2
C1A—C2A—H2A1	109.3	C1B—C2B—H2B1	109.2
C3A—C2A—H2A2	109.3	C3B—C2B—H2B2	109.2
C1A—C2A—H2A2	109.3	C1B—C2B—H2B2	109.2
H2A1—C2A—H2A2	107.9	H2B1—C2B—H2B2	107.9
C2A—C3A—C4A	109.23 (15)	C2B—C3B—C4B	108.50 (14)
C2A—C3A—H3A1	109.8	C2B—C3B—H3B1	110.0
C4A—C3A—H3A1	109.8	C4B—C3B—H3B1	110.0
C2A—C3A—H3A2	109.8	C2B—C3B—H3B2	110.0
C4A—C3A—H3A2	109.8	C4B—C3B—H3B2	110.0
H3A1—C3A—H3A2	108.3	H3B1—C3B—H3B2	108.4
C3A—C4A—C5A	111.35 (14)	C3B—C4B—C5B	111.49 (15)
C3A—C4A—H4A1	109.4	C3B—C4B—H4B1	109.3
C5A—C4A—H4A1	109.4	C5B—C4B—H4B1	109.3
C3A—C4A—H4A2	109.4	C3B—C4B—H4B2	109.3
C5A—C4A—H4A2	109.4	C5B—C4B—H4B2	109.3
H4A1—C4A—H4A2	108.0	H4B1—C4B—H4B2	108.0
N1A—C5A—C14A	111.10 (11)	N1B—C5B—C14B	110.83 (11)
N1A—C5A—C4A	110.20 (12)	N1B—C5B—C4B	111.55 (12)
C14A—C5A—C4A	110.75 (12)	C14B—C5B—C4B	110.40 (12)
N1A—C5A—H5A	108.2	N1B—C5B—H5B	108.0
C14A—C5A—H5A	108.2	C14B—C5B—H5B	108.0
C4A—C5A—H5A	108.2	C4B—C5B—H5B	108.0
N1A—C6A—C7A	116.71 (12)	N1B—C6B—C7B	113.99 (12)
N1A—C6A—H6A1	108.1	N1B—C6B—H6B1	108.8
C7A—C6A—H6A1	108.1	C7B—C6B—H6B1	108.8
N1A—C6A—H6A2	108.1	N1B—C6B—H6B2	108.8
C7A—C6A—H6A2	108.1	C7B—C6B—H6B2	108.8
H6A1—C6A—H6A2	107.3	H6B1—C6B—H6B2	107.7
O1A—C7A—C6A	111.99 (14)	O1B—C7B—C6B	112.55 (13)
O1A—C7A—H7A1	109.2	O1B—C7B—H7B1	109.1
C6A—C7A—H7A1	109.2	C6B—C7B—H7B1	109.1
O1A—C7A—H7A2	109.2	O1B—C7B—H7B2	109.1
C6A—C7A—H7A2	109.2	C6B—C7B—H7B2	109.1
H7A1—C7A—H7A2	107.9	H7B1—C7B—H7B2	107.8
C9A—C8A—C13A	118.27 (17)	C9B—C8B—C13B	118.18 (16)
C9A—C8A—C1A	120.71 (17)	C9B—C8B—C1B	121.21 (15)
C13A—C8A—C1A	121.00 (16)	C13B—C8B—C1B	120.58 (14)
C8A—C9A—C10A	120.2 (2)	C8B—C9B—C10B	120.54 (18)
C8A—C9A—H9A	119.9	C8B—C9B—H9B	119.7
C10A—C9A—H9A	119.9	C10B—C9B—H9B	119.7
C11A—C10A—C9A	120.6 (2)	C11B—C10B—C9B	120.46 (19)
C11A—C10A—H10A	119.7	C11B—C10B—H10B	119.8
C9A—C10A—H10A	119.7	C9B—C10B—H10B	119.8
C12A—C11A—C10A	119.9 (2)	C10B—C11B—C12B	119.57 (19)
C12A—C11A—H11A	120.0	C10B—C11B—H11B	120.2
C10A—C11A—H11A	120.0	C12B—C11B—H11B	120.2
C11A—C12A—C13A	120.1 (2)	C11B—C12B—C13B	120.28 (19)
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.9
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.9
C8A—C13A—C12A	120.8 (2)	C12B—C13B—C8B	120.92 (17)
C8A—C13A—H13A	119.6	C12B—C13B—H13B	119.5
C12A—C13A—H13A	119.6	C8B—C13B—H13B	119.5
C19A—C14A—C15A	118.05 (17)	C19B—C14B—C15B	118.18 (14)
C19A—C14A—C5A	121.30 (15)	C19B—C14B—C5B	120.63 (13)
C15A—C14A—C5A	120.63 (16)	C15B—C14B—C5B	121.19 (14)
C16A—C15A—C14A	121.4 (2)	C16B—C15B—C14B	120.84 (16)
C16A—C15A—H15A	119.3	C16B—C15B—H15B	119.6
C14A—C15A—H15A	119.3	C14B—C15B—H15B	119.6
C17A—C16A—C15A	120.3 (2)	C17B—C16B—C15B	120.42 (17)
C17A—C16A—H16A	119.8	C17B—C16B—H16B	119.8
C15A—C16A—H16A	119.8	C15B—C16B—H16B	119.8
C16A—C17A—C18A	119.9 (2)	C16B—C17B—C18B	119.39 (17)
C16A—C17A—H17A	120.1	C16B—C17B—H17B	120.3
C18A—C17A—H17A	120.1	C18B—C17B—H17B	120.3
C17A—C18A—C19A	120.2 (2)	C17B—C18B—C19B	120.51 (17)
C17A—C18A—H18A	119.9	C17B—C18B—H18B	119.7
C19A—C18A—H18A	119.9	C19B—C18B—H18B	119.7
C14A—C19A—C18A	120.2 (2)	C18B—C19B—C14B	120.64 (15)
C14A—C19A—H19A	119.9	C18B—C19B—H19B	119.7
C18A—C19A—H19A	119.9	C14B—C19B—H19B	119.7
C6A—N1A—C1A	111.9 (1)	C6B—N1B—C5B	110.8 (1)
C6A—N1A—C5A	112.0 (1)	C6B—N1B—C1B	110.5 (1)
C1A—N1A—C5A	112.0 (1)	C5B—N1B—C1B	111.8 (1)
C7A—O1A—H1A1	109.5	C7B—O1B—H1B1	109.5
N1A—C1A—C2A—C3A	56.0 (2)	N1B—C1B—C2B—C3B	56.26 (19)
C8A—C1A—C2A—C3A	178.90 (16)	C8B—C1B—C2B—C3B	179.57 (14)
C1A—C2A—C3A—C4A	−55.3 (2)	C1B—C2B—C3B—C4B	−56.4 (2)
C2A—C3A—C4A—C5A	56.0 (2)	C2B—C3B—C4B—C5B	56.3 (2)
C3A—C4A—C5A—N1A	−57.20 (19)	C3B—C4B—C5B—N1B	−56.55 (19)
C3A—C4A—C5A—C14A	179.46 (15)	C3B—C4B—C5B—C14B	179.76 (14)
N1A—C6A—C7A—O1A	174.1 (1)	N1B—C6B—C7B—O1B	50.7 (2)
N1A—C1A—C8A—C9A	−129.20 (16)	N1B—C1B—C8B—C9B	−118.54 (16)
C2A—C1A—C8A—C9A	108.20 (19)	C2B—C1B—C8B—C9B	117.74 (17)
N1A—C1A—C8A—C13A	52.38 (19)	N1B—C1B—C8B—C13B	59.56 (18)
C2A—C1A—C8A—C13A	−70.2 (2)	C2B—C1B—C8B—C13B	−64.16 (19)
C13A—C8A—C9A—C10A	0.9 (3)	C13B—C8B—C9B—C10B	−1.7 (2)
C1A—C8A—C9A—C10A	−177.54 (18)	C1B—C8B—C9B—C10B	176.48 (15)
C8A—C9A—C10A—C11A	−0.5 (4)	C8B—C9B—C10B—C11B	0.2 (3)
C9A—C10A—C11A—C12A	0.0 (4)	C9B—C10B—C11B—C12B	1.6 (3)
C10A—C11A—C12A—C13A	0.2 (4)	C10B—C11B—C12B—C13B	−1.9 (3)
C9A—C8A—C13A—C12A	−0.7 (3)	C11B—C12B—C13B—C8B	0.4 (3)
C1A—C8A—C13A—C12A	177.71 (16)	C9B—C8B—C13B—C12B	1.4 (2)
C11A—C12A—C13A—C8A	0.2 (3)	C1B—C8B—C13B—C12B	−176.81 (15)
N1A—C5A—C14A—C19A	−60.63 (18)	N1B—C5B—C14B—C19B	−62.66 (17)
C4A—C5A—C14A—C19A	62.19 (18)	C4B—C5B—C14B—C19B	61.45 (17)
N1A—C5A—C14A—C15A	120.62 (15)	N1B—C5B—C14B—C15B	116.87 (15)
C4A—C5A—C14A—C15A	−116.56 (17)	C4B—C5B—C14B—C15B	−119.01 (16)
C19A—C14A—C15A—C16A	−0.2 (3)	C19B—C14B—C15B—C16B	1.0 (2)
C5A—C14A—C15A—C16A	178.58 (16)	C5B—C14B—C15B—C16B	−178.59 (14)
C14A—C15A—C16A—C17A	0.3 (3)	C14B—C15B—C16B—C17B	−0.1 (3)
C15A—C16A—C17A—C18A	0.0 (3)	C15B—C16B—C17B—C18B	−0.6 (3)
C16A—C17A—C18A—C19A	−0.3 (3)	C16B—C17B—C18B—C19B	0.4 (3)
C15A—C14A—C19A—C18A	−0.1 (2)	C17B—C18B—C19B—C14B	0.5 (2)
C5A—C14A—C19A—C18A	−178.89 (15)	C15B—C14B—C19B—C18B	−1.2 (2)
C17A—C18A—C19A—C14A	0.4 (3)	C5B—C14B—C19B—C18B	178.35 (14)
C7A—C6A—N1A—C1A	58.5 (2)	C7B—C6B—N1B—C5B	95.92 (15)
C7A—C6A—N1A—C5A	−68.14 (16)	C7B—C6B—N1B—C1B	−139.7 (1)
C8A—C1A—N1A—C6A	54.31 (16)	C14B—C5B—N1B—C6B	−57.81 (15)
C2A—C1A—N1A—C6A	176.51 (13)	C4B—C5B—N1B—C6B	178.75 (12)
C8A—C1A—N1A—C5A	−179.04 (12)	C14B—C5B—N1B—C1B	178.49 (12)
C2A—C1A—N1A—C5A	−56.83 (16)	C4B—C5B—N1B—C1B	55.04 (16)
C14A—C5A—N1A—C6A	−52.73 (16)	C8B—C1B—N1B—C6B	57.87 (15)
C4A—C5A—N1A—C6A	−175.86 (12)	C2B—C1B—N1B—C6B	−178.50 (13)
C14A—C5A—N1A—C1A	−179.31 (12)	C8B—C1B—N1B—C5B	−178.30 (12)
C4A—C5A—N1A—C1A	57.56 (16)	C2B—C1B—N1B—C5B	−54.66 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B1···N1B	0.82	2.54	2.884 (2)	107
C7B—H7B2···Cg	0.97	2.66	3.528 (2)	149
O1A—H1A1···O1B^i	0.82	1.93	2.744 (2)	170
O1B—H1B1···O1A^ii	0.82	2.09	2.816 (2)	148

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z.