A 1:1 diastereoisomeric complex of trans-2-{[(R)-(+)-1-phenyl­ethyl­amino]­carbonyl}cyclo­hexane­carboxyl­ic acid

A novel cyclo­hexane­carboxyl­ic acid derivative, C₁₆H₂₁NO₃, having a chiral amide group, was synthesized and its crystal structure has been determined. The crystal structure contains two diastereoisomers, namely (1R,2R)- and (1S,2S)-trans-2-{[(R)-(+)-1-phenyl­ethyl­amino]­carbonyl}cyclo­hexane­carboxyl­ic acid.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.103
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         20

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               3662
           Count of symmetry unique reflns         3662
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN and Mercury (Bruno et al., 2002); software used to prepare material for publication: TEXSAN and Mercury.

trans-2-{[(R)-(+)-1-Phenylethylamino]carbonyl}cyclohexanecarboxylic acid

Crystal data

C16H21NO3	F(000) = 592
Mr = 275.34	Dx = 1.188 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 13296 reflections
a = 9.6306 (6) Å	θ = 2.4–27.5°
b = 15.3825 (8) Å	µ = 0.08 mm^−1
c = 10.8903 (6) Å	T = 173 K
β = 107.456 (2)°	Block, colorless
V = 1539.02 (15) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	3161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
Detector resolution: 10.00 pixels mm^-1	h = −12→12
ω scans	k = −19→19
6718 measured reflections	l = −14→14
3662 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0647P)^2] where P = (Fo^2 + 2Fc^2)/3
3662 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.21 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
O1A	0.44576 (16)	0.56500 (11)	0.75729 (14)	0.0315 (3)
O1B	−0.05119 (16)	0.50356 (14)	0.76275 (15)	0.0414 (4)
O2A	0.76413 (19)	0.69706 (11)	0.93908 (17)	0.0394 (4)
O2B	0.2807 (2)	0.39292 (12)	0.96409 (19)	0.0460 (4)
O3A	0.6071 (2)	0.73563 (12)	1.0433 (2)	0.0514 (5)
H1OA	0.6326	0.7858	1.0285	0.062*
O3B	0.1211 (2)	0.35591 (12)	1.0656 (2)	0.0492 (5)
H1OB	0.1461	0.3055	1.0514	0.059*
N1A	0.63040 (19)	0.51469 (14)	0.68813 (16)	0.0308 (4)
H1NA	0.7245	0.5041	0.7098	0.037*
N1B	0.13922 (19)	0.53343 (13)	0.68804 (17)	0.0299 (4)
H1NB	0.2310	0.5497	0.7092	0.036*
C1A	0.6741 (2)	0.67776 (13)	0.9925 (2)	0.0284 (4)
C1B	0.1873 (2)	0.41312 (14)	1.0124 (2)	0.0308 (5)
C2A	0.6329 (2)	0.58569 (13)	1.0124 (2)	0.0257 (4)
H2A	0.5256	0.5839	0.9993	0.031*
C2B	0.1389 (2)	0.50544 (14)	1.0205 (2)	0.0282 (4)
H2B	0.0323	0.5055	1.0106	0.034*
C3A	0.6674 (2)	0.52264 (13)	0.91731 (18)	0.0240 (4)
H3A	0.7721	0.5289	0.9214	0.029*
C3B	0.1659 (2)	0.56102 (15)	0.91277 (19)	0.0264 (4)
H3B	0.2712	0.5570	0.9182	0.032*
C4A	0.6379 (3)	0.42779 (14)	0.9492 (2)	0.0321 (5)
H4A1	0.5318	0.4195	0.9321	0.039*
H4A2	0.6706	0.3880	0.8921	0.039*
C4B	0.1278 (3)	0.65668 (15)	0.9266 (2)	0.0335 (5)
H4B1	0.1539	0.6916	0.8604	0.040*
H4B2	0.0215	0.6621	0.9113	0.040*
C5A	0.7159 (3)	0.40424 (16)	1.0895 (2)	0.0382 (5)
H5A1	0.6891	0.3444	1.1069	0.046*
H5A2	0.8225	0.4059	1.1045	0.046*
C5B	0.2076 (3)	0.69289 (17)	1.0599 (2)	0.0393 (5)
H5B1	0.3133	0.6950	1.0708	0.047*
H5B2	0.1739	0.7530	1.0670	0.047*
C6A	0.6756 (3)	0.46668 (17)	1.1805 (2)	0.0389 (6)
H6A1	0.7296	0.4512	1.2704	0.047*
H6A2	0.5702	0.4618	1.1702	0.047*
C6B	0.1804 (3)	0.63718 (17)	1.1657 (2)	0.0396 (6)
H6B1	0.2383	0.6601	1.2505	0.048*
H6B2	0.0762	0.6407	1.1608	0.048*
C7A	0.7117 (3)	0.56003 (17)	1.1538 (2)	0.0358 (5)
H7A1	0.8181	0.5659	1.1707	0.043*
H7A2	0.6816	0.5999	1.2125	0.043*
C7B	0.2210 (3)	0.54281 (16)	1.1541 (2)	0.0360 (5)
H7B1	0.1972	0.5081	1.2217	0.043*
H7B2	0.3272	0.5385	1.1680	0.043*
C8A	0.5723 (2)	0.53812 (12)	0.7800 (2)	0.0237 (4)
C8B	0.0753 (2)	0.52863 (14)	0.7814 (2)	0.0273 (4)
C9A	0.5442 (2)	0.50576 (16)	0.55234 (19)	0.0313 (5)
H9A	0.4389	0.5074	0.5476	0.038*
C9B	0.0654 (2)	0.51330 (15)	0.55302 (19)	0.0298 (4)
H9B	−0.0417	0.5164	0.5404	0.036*
C10A	0.5731 (3)	0.58124 (17)	0.4723 (2)	0.0456 (6)
H10A	0.5537	0.6363	0.5092	0.068*
H10B	0.5093	0.5761	0.3836	0.068*
H10C	0.6750	0.5797	0.4726	0.068*
C10B	0.1020 (3)	0.58353 (16)	0.4692 (2)	0.0383 (5)
H10D	0.0777	0.6407	0.4968	0.057*
H10E	0.0456	0.5737	0.3791	0.057*
H10F	0.2061	0.5814	0.4777	0.057*
C11A	0.5735 (2)	0.41940 (15)	0.49771 (19)	0.0293 (4)
C11B	0.0989 (2)	0.42201 (15)	0.5166 (2)	0.0309 (5)
C12A	0.7110 (2)	0.38297 (16)	0.5275 (2)	0.0348 (5)
H12A	0.7899	0.4101	0.5897	0.042*
C12B	0.1781 (3)	0.36218 (18)	0.6060 (2)	0.0477 (6)
H12B	0.2166	0.3783	0.6939	0.057*
C13A	0.7349 (3)	0.30736 (17)	0.4677 (3)	0.0436 (6)
H13A	0.8300	0.2832	0.4891	0.052*
C13B	0.2009 (4)	0.2790 (2)	0.5670 (3)	0.0608 (8)
H13B	0.2549	0.2385	0.6290	0.073*
C14A	0.6215 (3)	0.26686 (18)	0.3771 (3)	0.0477 (6)
H14A	0.6384	0.2157	0.3349	0.057*
C14B	0.1467 (3)	0.25389 (18)	0.4403 (3)	0.0506 (7)
H14B	0.1630	0.1966	0.4150	0.061*
C15A	0.4842 (3)	0.30140 (18)	0.3487 (2)	0.0459 (6)
H15A	0.4053	0.2730	0.2881	0.055*
C15B	0.0688 (3)	0.31245 (19)	0.3508 (3)	0.0434 (6)
H15B	0.0308	0.2957	0.2631	0.052*
C16A	0.4590 (3)	0.37733 (16)	0.4073 (2)	0.0365 (5)
H16A	0.3635	0.4009	0.3859	0.044*
C16B	0.0455 (2)	0.39566 (17)	0.3879 (2)	0.0369 (5)
H16B	−0.0077	0.4358	0.3250	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0241 (7)	0.0376 (8)	0.0325 (8)	0.0050 (6)	0.0083 (6)	0.0006 (7)
O1B	0.0243 (8)	0.0634 (12)	0.0363 (8)	−0.0070 (8)	0.0088 (6)	−0.0064 (8)
O2A	0.0461 (9)	0.0295 (8)	0.0520 (10)	−0.0027 (7)	0.0290 (8)	−0.0022 (7)
O2B	0.0489 (10)	0.0317 (9)	0.0700 (12)	0.0081 (8)	0.0369 (9)	0.0101 (9)
O3A	0.0584 (12)	0.0290 (9)	0.0852 (15)	−0.0045 (8)	0.0493 (11)	−0.0117 (9)
O3B	0.0607 (12)	0.0304 (8)	0.0731 (13)	0.0058 (9)	0.0450 (10)	0.0081 (9)
N1A	0.0214 (8)	0.0447 (11)	0.0245 (8)	0.0020 (8)	0.0044 (6)	−0.0035 (8)
N1B	0.0239 (8)	0.0379 (10)	0.0267 (8)	−0.0041 (8)	0.0057 (7)	−0.0039 (8)
C1A	0.0262 (10)	0.0276 (11)	0.0311 (10)	0.0009 (8)	0.0079 (8)	−0.0019 (9)
C1B	0.0318 (11)	0.0312 (11)	0.0313 (10)	−0.0009 (9)	0.0123 (9)	0.0015 (9)
C2A	0.0249 (10)	0.0266 (10)	0.0269 (10)	−0.0010 (8)	0.0095 (8)	−0.0020 (8)
C2B	0.0265 (10)	0.0297 (10)	0.0302 (10)	0.0015 (9)	0.0111 (8)	−0.0001 (9)
C3A	0.0220 (9)	0.0242 (10)	0.0251 (9)	0.0001 (8)	0.0061 (7)	−0.0009 (8)
C3B	0.0227 (9)	0.0326 (10)	0.0242 (9)	−0.0001 (8)	0.0073 (7)	−0.0006 (9)
C4A	0.0377 (12)	0.0263 (10)	0.0318 (10)	0.0017 (9)	0.0097 (9)	0.0017 (9)
C4B	0.0369 (12)	0.0310 (11)	0.0332 (11)	0.0023 (9)	0.0114 (9)	0.0030 (9)
C5A	0.0455 (13)	0.0349 (13)	0.0343 (11)	0.0076 (10)	0.0122 (10)	0.0081 (10)
C5B	0.0467 (14)	0.0331 (11)	0.0397 (12)	−0.0029 (11)	0.0157 (11)	−0.0037 (10)
C6A	0.0457 (14)	0.0420 (14)	0.0309 (11)	0.0054 (11)	0.0143 (10)	0.0078 (10)
C6B	0.0526 (15)	0.0357 (12)	0.0322 (11)	0.0004 (11)	0.0153 (10)	−0.0038 (10)
C7A	0.0407 (13)	0.0423 (13)	0.0247 (10)	−0.0005 (10)	0.0103 (9)	−0.0022 (9)
C7B	0.0446 (13)	0.0366 (13)	0.0261 (10)	0.0039 (10)	0.0094 (9)	0.0017 (9)
C8A	0.0229 (10)	0.0198 (9)	0.0282 (9)	−0.0031 (7)	0.0074 (7)	−0.0007 (8)
C8B	0.0217 (10)	0.0301 (10)	0.0291 (10)	0.0013 (8)	0.0059 (8)	−0.0004 (9)
C9A	0.0248 (9)	0.0416 (12)	0.0246 (9)	0.0044 (9)	0.0032 (8)	−0.0039 (9)
C9B	0.0284 (10)	0.0337 (11)	0.0260 (10)	0.0005 (9)	0.0064 (8)	−0.0007 (9)
C10A	0.0663 (17)	0.0363 (13)	0.0314 (12)	0.0079 (12)	0.0105 (11)	0.0008 (10)
C10B	0.0458 (13)	0.0355 (12)	0.0325 (11)	0.0010 (10)	0.0100 (10)	0.0036 (10)
C11A	0.0314 (11)	0.0322 (11)	0.0244 (9)	−0.0048 (9)	0.0088 (8)	−0.0015 (9)
C11B	0.0278 (10)	0.0344 (11)	0.0311 (10)	−0.0055 (9)	0.0096 (8)	−0.0023 (9)
C12A	0.0310 (11)	0.0329 (11)	0.0403 (11)	−0.0039 (9)	0.0102 (9)	−0.0049 (10)
C12B	0.0648 (17)	0.0426 (14)	0.0337 (12)	0.0074 (13)	0.0119 (11)	0.0032 (11)
C13A	0.0417 (13)	0.0342 (13)	0.0579 (16)	0.0001 (11)	0.0194 (12)	−0.0036 (12)
C13B	0.085 (2)	0.0429 (16)	0.0532 (17)	0.0173 (15)	0.0184 (15)	0.0110 (13)
C14A	0.0652 (18)	0.0310 (12)	0.0495 (14)	−0.0074 (12)	0.0212 (13)	−0.0087 (11)
C14B	0.0645 (18)	0.0345 (13)	0.0585 (16)	−0.0008 (12)	0.0271 (14)	−0.0069 (12)
C15A	0.0541 (16)	0.0391 (14)	0.0397 (13)	−0.0161 (12)	0.0069 (11)	−0.0105 (11)
C15B	0.0440 (14)	0.0441 (14)	0.0439 (13)	−0.0120 (12)	0.0161 (11)	−0.0134 (12)
C16A	0.0317 (11)	0.0398 (13)	0.0332 (10)	−0.0042 (10)	0.0024 (9)	0.0001 (10)
C16B	0.0332 (12)	0.0402 (13)	0.0342 (11)	−0.0032 (10)	0.0054 (9)	0.0002 (10)

Geometric parameters (Å, º)

O1A—C8A	1.239 (2)	C6A—H6A2	0.9900
O1B—C8B	1.235 (3)	C6B—C7B	1.518 (3)
O2A—C1A	1.217 (3)	C6B—H6B1	0.9900
O2B—C1B	1.211 (3)	C6B—H6B2	0.9900
O3A—C1A	1.315 (3)	C7A—H7A1	0.9900
O3A—H1OA	0.8400	C7A—H7A2	0.9900
O3B—C1B	1.318 (3)	C7B—H7B1	0.9900
O3B—H1OB	0.8400	C7B—H7B2	0.9900
N1A—C8A	1.334 (3)	C9A—C11A	1.516 (3)
N1A—C9A	1.469 (2)	C9A—C10A	1.527 (4)
N1A—H1NA	0.8800	C9A—H9A	1.0000
N1B—C8B	1.339 (3)	C9B—C11B	1.520 (3)
N1B—C9B	1.462 (3)	C9B—C10B	1.522 (3)
N1B—H1NB	0.8800	C9B—H9B	1.0000
C1A—C2A	1.504 (3)	C10A—H10A	0.9800
C1B—C2B	1.505 (3)	C10A—H10B	0.9800
C2A—C3A	1.527 (3)	C10A—H10C	0.9800
C2A—C7A	1.550 (3)	C10B—H10D	0.9800
C2A—H2A	1.0000	C10B—H10E	0.9800
C2B—C3B	1.536 (3)	C10B—H10F	0.9800
C2B—C7B	1.544 (3)	C11A—C12A	1.384 (3)
C2B—H2B	1.0000	C11A—C16A	1.397 (3)
C3A—C8A	1.520 (3)	C11B—C12B	1.389 (4)
C3A—C4A	1.546 (3)	C11B—C16B	1.400 (3)
C3A—H3A	1.0000	C12A—C13A	1.386 (3)
C3B—C8B	1.519 (3)	C12A—H12A	0.9500
C3B—C4B	1.535 (3)	C12B—C13B	1.387 (4)
C3B—H3B	1.0000	C12B—H12B	0.9500
C4A—C5A	1.530 (3)	C13A—C14A	1.381 (4)
C4A—H4A1	0.9900	C13A—H13A	0.9500
C4A—H4A2	0.9900	C13B—C14B	1.376 (4)
C4B—C5B	1.529 (3)	C13B—H13B	0.9500
C4B—H4B1	0.9900	C14A—C15A	1.372 (4)
C4B—H4B2	0.9900	C14A—H14A	0.9500
C5A—C6A	1.512 (3)	C14B—C15B	1.373 (4)
C5A—H5A1	0.9900	C14B—H14B	0.9500
C5A—H5A2	0.9900	C15A—C16A	1.387 (4)
C5B—C6B	1.520 (4)	C15A—H15A	0.9500
C5B—H5B1	0.9900	C15B—C16B	1.381 (4)
C5B—H5B2	0.9900	C15B—H15B	0.9500
C6A—C7A	1.526 (4)	C16A—H16A	0.9500
C6A—H6A1	0.9900	C16B—H16B	0.9500
C1A—O3A—H1OA	109.5	C2A—C7A—H7A1	109.4
C1B—O3B—H1OB	109.5	C6A—C7A—H7A2	109.4
C8A—N1A—C9A	122.86 (17)	C2A—C7A—H7A2	109.4
C8A—N1A—H1NA	118.6	H7A1—C7A—H7A2	108.0
C9A—N1A—H1NA	118.6	C6B—C7B—C2B	111.23 (19)
C8B—N1B—C9B	123.81 (18)	C6B—C7B—H7B1	109.4
C8B—N1B—H1NB	118.1	C2B—C7B—H7B1	109.4
C9B—N1B—H1NB	118.1	C6B—C7B—H7B2	109.4
O2A—C1A—O3A	123.1 (2)	C2B—C7B—H7B2	109.4
O2A—C1A—C2A	123.7 (2)	H7B1—C7B—H7B2	108.0
O3A—C1A—C2A	113.15 (19)	O1A—C8A—N1A	123.32 (18)
O2B—C1B—O3B	122.7 (2)	O1A—C8A—C3A	120.99 (18)
O2B—C1B—C2B	123.4 (2)	N1A—C8A—C3A	115.50 (17)
O3B—C1B—C2B	113.91 (19)	O1B—C8B—N1B	123.21 (19)
C1A—C2A—C3A	112.33 (18)	O1B—C8B—C3B	121.08 (19)
C1A—C2A—C7A	108.13 (17)	N1B—C8B—C3B	115.62 (17)
C3A—C2A—C7A	111.75 (17)	N1A—C9A—C11A	111.19 (18)
C1A—C2A—H2A	108.2	N1A—C9A—C10A	111.0 (2)
C3A—C2A—H2A	108.2	C11A—C9A—C10A	110.79 (18)
C7A—C2A—H2A	108.2	N1A—C9A—H9A	107.9
C1B—C2B—C3B	110.76 (18)	C11A—C9A—H9A	107.9
C1B—C2B—C7B	109.04 (17)	C10A—C9A—H9A	107.9
C3B—C2B—C7B	110.90 (18)	N1B—C9B—C11B	112.40 (18)
C1B—C2B—H2B	108.7	N1B—C9B—C10B	108.83 (18)
C3B—C2B—H2B	108.7	C11B—C9B—C10B	113.16 (18)
C7B—C2B—H2B	108.7	N1B—C9B—H9B	107.4
C8A—C3A—C2A	112.21 (16)	C11B—C9B—H9B	107.4
C8A—C3A—C4A	105.78 (16)	C10B—C9B—H9B	107.4
C2A—C3A—C4A	110.79 (17)	C9A—C10A—H10A	109.5
C8A—C3A—H3A	109.3	C9A—C10A—H10B	109.5
C2A—C3A—H3A	109.3	H10A—C10A—H10B	109.5
C4A—C3A—H3A	109.3	C9A—C10A—H10C	109.5
C8B—C3B—C4B	108.69 (17)	H10A—C10A—H10C	109.5
C8B—C3B—C2B	110.87 (18)	H10B—C10A—H10C	109.5
C4B—C3B—C2B	111.04 (18)	C9B—C10B—H10D	109.5
C8B—C3B—H3B	108.7	C9B—C10B—H10E	109.5
C4B—C3B—H3B	108.7	H10D—C10B—H10E	109.5
C2B—C3B—H3B	108.7	C9B—C10B—H10F	109.5
C5A—C4A—C3A	112.32 (18)	H10D—C10B—H10F	109.5
C5A—C4A—H4A1	109.1	H10E—C10B—H10F	109.5
C3A—C4A—H4A1	109.1	C12A—C11A—C16A	118.3 (2)
C5A—C4A—H4A2	109.1	C12A—C11A—C9A	122.71 (19)
C3A—C4A—H4A2	109.1	C16A—C11A—C9A	118.8 (2)
H4A1—C4A—H4A2	107.9	C12B—C11B—C16B	118.0 (2)
C5B—C4B—C3B	112.07 (19)	C12B—C11B—C9B	122.9 (2)
C5B—C4B—H4B1	109.2	C16B—C11B—C9B	119.1 (2)
C3B—C4B—H4B1	109.2	C11A—C12A—C13A	120.8 (2)
C5B—C4B—H4B2	109.2	C11A—C12A—H12A	119.6
C3B—C4B—H4B2	109.2	C13A—C12A—H12A	119.6
H4B1—C4B—H4B2	107.9	C13B—C12B—C11B	120.1 (2)
C6A—C5A—C4A	111.0 (2)	C13B—C12B—H12B	120.0
C6A—C5A—H5A1	109.4	C11B—C12B—H12B	120.0
C4A—C5A—H5A1	109.4	C14A—C13A—C12A	120.5 (2)
C6A—C5A—H5A2	109.4	C14A—C13A—H13A	119.8
C4A—C5A—H5A2	109.4	C12A—C13A—H13A	119.8
H5A1—C5A—H5A2	108.0	C14B—C13B—C12B	121.2 (3)
C6B—C5B—C4B	111.3 (2)	C14B—C13B—H13B	119.4
C6B—C5B—H5B1	109.4	C12B—C13B—H13B	119.4
C4B—C5B—H5B1	109.4	C15A—C14A—C13A	119.3 (2)
C6B—C5B—H5B2	109.4	C15A—C14A—H14A	120.4
C4B—C5B—H5B2	109.4	C13A—C14A—H14A	120.4
H5B1—C5B—H5B2	108.0	C15B—C14B—C13B	119.3 (3)
C5A—C6A—C7A	110.8 (2)	C15B—C14B—H14B	120.3
C5A—C6A—H6A1	109.5	C13B—C14B—H14B	120.3
C7A—C6A—H6A1	109.5	C14A—C15A—C16A	120.8 (2)
C5A—C6A—H6A2	109.5	C14A—C15A—H15A	119.6
C7A—C6A—H6A2	109.5	C16A—C15A—H15A	119.6
H6A1—C6A—H6A2	108.1	C14B—C15B—C16B	120.2 (2)
C7B—C6B—C5B	111.7 (2)	C14B—C15B—H15B	119.9
C7B—C6B—H6B1	109.3	C16B—C15B—H15B	119.9
C5B—C6B—H6B1	109.3	C15A—C16A—C11A	120.3 (2)
C7B—C6B—H6B2	109.3	C15A—C16A—H16A	119.8
C5B—C6B—H6B2	109.3	C11A—C16A—H16A	119.9
H6B1—C6B—H6B2	107.9	C15B—C16B—C11B	121.2 (2)
C6A—C7A—C2A	110.98 (19)	C15B—C16B—H16B	119.4
C6A—C7A—H7A1	109.4	C11B—C16B—H16B	119.4
O2A—C1A—C2A—C3A	−22.3 (3)	C4A—C3A—C8A—N1A	−86.3 (2)
O3A—C1A—C2A—C3A	160.26 (19)	C9B—N1B—C8B—O1B	2.7 (4)
O2A—C1A—C2A—C7A	101.5 (2)	C9B—N1B—C8B—C3B	−173.99 (19)
O3A—C1A—C2A—C7A	−76.0 (2)	C4B—C3B—C8B—O1B	−82.7 (3)
O2B—C1B—C2B—C3B	25.9 (3)	C2B—C3B—C8B—O1B	39.6 (3)
O3B—C1B—C2B—C3B	−155.63 (19)	C4B—C3B—C8B—N1B	94.1 (2)
O2B—C1B—C2B—C7B	−96.4 (3)	C2B—C3B—C8B—N1B	−143.63 (19)
O3B—C1B—C2B—C7B	82.1 (2)	C8A—N1A—C9A—C11A	−130.1 (2)
C1A—C2A—C3A—C8A	−67.7 (2)	C8A—N1A—C9A—C10A	106.1 (2)
C7A—C2A—C3A—C8A	170.60 (18)	C8B—N1B—C9B—C11B	−98.8 (2)
C1A—C2A—C3A—C4A	174.36 (17)	C8B—N1B—C9B—C10B	135.1 (2)
C7A—C2A—C3A—C4A	52.6 (2)	N1A—C9A—C11A—C12A	−39.5 (3)
C1B—C2B—C3B—C8B	63.5 (2)	C10A—C9A—C11A—C12A	84.5 (3)
C7B—C2B—C3B—C8B	−175.33 (18)	N1A—C9A—C11A—C16A	144.7 (2)
C1B—C2B—C3B—C4B	−175.61 (18)	C10A—C9A—C11A—C16A	−91.3 (2)
C7B—C2B—C3B—C4B	−54.4 (2)	N1B—C9B—C11B—C12B	6.6 (3)
C8A—C3A—C4A—C5A	−174.88 (18)	C10B—C9B—C11B—C12B	130.3 (2)
C2A—C3A—C4A—C5A	−53.1 (2)	N1B—C9B—C11B—C16B	−174.92 (19)
C8B—C3B—C4B—C5B	176.45 (19)	C10B—C9B—C11B—C16B	−51.1 (3)
C2B—C3B—C4B—C5B	54.2 (2)	C16A—C11A—C12A—C13A	1.0 (3)
C3A—C4A—C5A—C6A	55.6 (3)	C9A—C11A—C12A—C13A	−174.9 (2)
C3B—C4B—C5B—C6B	−54.5 (3)	C16B—C11B—C12B—C13B	−0.7 (4)
C4A—C5A—C6A—C7A	−57.5 (3)	C9B—C11B—C12B—C13B	177.9 (3)
C4B—C5B—C6B—C7B	55.4 (3)	C11A—C12A—C13A—C14A	−0.1 (4)
C5A—C6A—C7A—C2A	57.3 (3)	C11B—C12B—C13B—C14B	0.2 (5)
C1A—C2A—C7A—C6A	−179.52 (19)	C12A—C13A—C14A—C15A	−1.2 (4)
C3A—C2A—C7A—C6A	−55.4 (2)	C12B—C13B—C14B—C15B	0.1 (5)
C5B—C6B—C7B—C2B	−56.2 (3)	C13A—C14A—C15A—C16A	1.6 (4)
C1B—C2B—C7B—C6B	177.9 (2)	C13B—C14B—C15B—C16B	0.1 (4)
C3B—C2B—C7B—C6B	55.6 (3)	C14A—C15A—C16A—C11A	−0.8 (4)
C9A—N1A—C8A—O1A	−9.6 (3)	C12A—C11A—C16A—C15A	−0.5 (3)
C9A—N1A—C8A—C3A	165.5 (2)	C9A—C11A—C16A—C15A	175.5 (2)
C2A—C3A—C8A—O1A	−32.0 (3)	C14B—C15B—C16B—C11B	−0.6 (4)
C4A—C3A—C8A—O1A	88.9 (2)	C12B—C11B—C16B—C15B	0.9 (4)
C2A—C3A—C8A—N1A	152.82 (18)	C9B—C11B—C16B—C15B	−177.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3A—H1OA···O2B^i	0.84	1.84	2.661 (3)	166
O3B—H1OB···O2A^ii	0.84	1.87	2.688 (3)	166
N1A—H1NA···O1B^iii	0.88	2.06	2.932 (2)	170
N1B—H1NB···O1A	0.88	1.99	2.861 (2)	170

Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+2; (iii) x+1, y, z.