Venlafaxine besylate monohydrate.

The title compound {systematic name: [2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]dimethylazanium benzene-sulfonate monohydrate}, C17H28NO2 (+)·C6H5O3S(-)·H2O, is a besylate salt hydrate of the anti-depressant drug venlafaxine. In the crystal, besylate anions and water mol-ecules self-assemble, forming hydrogen-bonded dimers linked around inversion centers, with graph set R 4 (4)(6). The crystal packing features a chain of alternate dimers and venlafaxine cations in the b-axis direction with the components linked by O-H⋯O hydrogen bonds and C-H⋯O and C-H⋯π inter-actions. This is the first example of a venlafaxine cation with a closed conformation, as it features an intra-molecular N-H⋯O inter-action involving the protonated N atom.

Related literature

For background information, see: Venu et al. (2008 ▶); Tessler & Goldberg (2004 ▶); Van Eupen et al. (2008 ▶); Yardley et al. (1990 ▶); Banjeree et al. (2005 ▶); Vega et al. (2000 ▶); Sivalakshmidevi et al. (2002 ▶); Roy et al. (2007 ▶). For ring-puckering calculations, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C17H28NO2 +·C6H5O3S−·H2O

M = 453.58

Triclinic,

a = 10.1163 (5) Å

b = 10.2176 (4) Å

c = 13.8162 (6) Å

α = 72.074 (4)°

β = 70.108 (4)°

γ = 63.889 (5)°

V = 1184.53 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.70 × 0.30 × 0.10 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.842, T max = 1.000

10063 measured reflections

5366 independent reflections

3072 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.163

S = 1.02

5366 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813027542/gg2130sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027542/gg2130Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027542/gg2130Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H28NO2+·C6H5O3S−·H2O	Z = 2
Mr = 453.58	F(000) = 488
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1163 (5) Å	Cell parameters from 3716 reflections
b = 10.2176 (4) Å	θ = 3.8–28.8°
c = 13.8162 (6) Å	µ = 0.17 mm−1
α = 72.074 (4)°	T = 293 K
β = 70.108 (4)°	Prism, colourless
γ = 63.889 (5)°	0.70 × 0.30 × 0.10 mm
V = 1184.53 (11) Å3

Agilent Xcalibur (Eos, Gemini) diffractometer	5366 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 16.1158 pixels mm-1	θmax = 28.8°, θmin = 3.8°
ω scans	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→13
Tmin = 0.842, Tmax = 1.000	l = −17→17
10063 measured reflections

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)] = 0.053	Hydrogen site location: mixed
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0896P)2] where P = (Fo2 + 2Fc2)/3
5366 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1498 (2)	0.4789 (2)	0.26437 (16)	0.0404 (5)
C2	0.1147 (3)	0.6298 (2)	0.22570 (18)	0.0460 (5)
H2	0.1656	0.6771	0.2385	0.055*
C3	0.0063 (3)	0.7108 (2)	0.16894 (18)	0.0484 (6)
H3	−0.0147	0.8116	0.1436	0.058*
C4	−0.0715 (3)	0.6434 (2)	0.14941 (17)	0.0447 (5)
C5	−0.0402 (3)	0.4941 (2)	0.18763 (18)	0.0479 (6)
H5	−0.0923	0.4476	0.1752	0.057*
C6	0.0686 (3)	0.4143 (2)	0.24438 (18)	0.0471 (6)
H6	0.0885	0.3137	0.2702	0.057*
C7	0.2715 (3)	0.3927 (2)	0.32531 (16)	0.0424 (5)
H7	0.2842	0.4664	0.3493	0.051*
C8	0.4301 (2)	0.3089 (2)	0.25829 (15)	0.0381 (5)
C9	0.4845 (3)	0.4202 (2)	0.16915 (16)	0.0429 (5)
H9A	0.4120	0.4721	0.1257	0.051*
H9B	0.4879	0.4931	0.1987	0.051*
C10	0.6391 (3)	0.3478 (3)	0.10163 (18)	0.0533 (6)
H10A	0.7138	0.3052	0.1431	0.064*
H10B	0.6655	0.4224	0.0446	0.064*
C11	0.6436 (3)	0.2272 (3)	0.05707 (19)	0.0633 (7)
H11A	0.7460	0.1782	0.0184	0.076*
H11B	0.5777	0.2710	0.0090	0.076*
C12	0.5921 (3)	0.1142 (3)	0.1451 (2)	0.0644 (7)
H12A	0.6645	0.0630	0.1886	0.077*
H12B	0.5896	0.0411	0.1153	0.077*
C13	0.4353 (3)	0.1876 (2)	0.21283 (18)	0.0506 (6)
H13A	0.4083	0.1130	0.2697	0.061*
H13B	0.3612	0.2304	0.1709	0.061*
C14	0.2189 (3)	0.2928 (3)	0.42343 (17)	0.0492 (6)
H14A	0.1121	0.3436	0.4529	0.059*
H14B	0.2303	0.2038	0.4046	0.059*
C15	0.2630 (3)	0.3696 (3)	0.5604 (2)	0.0605 (7)
H15A	0.3226	0.3349	0.6109	0.073*
H15B	0.1574	0.3994	0.5955	0.073*
H15C	0.2817	0.4528	0.5108	0.073*
C16	0.2888 (4)	0.1159 (3)	0.5811 (2)	0.0655 (7)
H16A	0.3171	0.0381	0.5443	0.079*
H16B	0.1854	0.1393	0.6206	0.079*
H16C	0.3535	0.0837	0.6279	0.079*
C17	−0.2610 (3)	0.6691 (3)	0.0731 (2)	0.0761 (9)
H17A	−0.3315	0.7430	0.0331	0.091*
H17B	−0.3155	0.6286	0.1384	0.091*
H17C	−0.1928	0.5913	0.0344	0.091*
N1	0.3050 (2)	0.2494 (2)	0.50483 (14)	0.0416 (5)
H1	0.390 (3)	0.232 (3)	0.4746 (19)	0.050*
O1	−0.1776 (2)	0.73441 (18)	0.09278 (14)	0.0630 (5)
O2	0.53164 (17)	0.23490 (16)	0.32729 (11)	0.0431 (4)
H2A	0.569 (3)	0.291 (3)	0.326 (2)	0.065*
S1B	0.31436 (9)	0.78902 (7)	0.40428 (6)	0.0623 (2)
C1B	0.2016 (4)	1.0171 (3)	0.1316 (2)	0.0693 (8)
H1B	0.2502	1.0263	0.0607	0.083*
C2B	0.2834 (3)	0.9237 (3)	0.2047 (2)	0.0603 (7)
H2B	0.3869	0.8709	0.1833	0.072*
C3B	0.2115 (3)	0.9089 (2)	0.30976 (18)	0.0436 (5)
C4B	0.0585 (3)	0.9889 (3)	0.3397 (2)	0.0551 (6)
H4B	0.0086	0.9808	0.4103	0.066*
C5B	−0.0207 (3)	1.0810 (3)	0.2649 (2)	0.0671 (7)
H5B	−0.1244	1.1339	0.2853	0.080*
C6B	0.0514 (4)	1.0953 (3)	0.1618 (2)	0.0675 (8)
H6B	−0.0027	1.1590	0.1119	0.081*
O1B	0.3786 (3)	0.8685 (2)	0.42970 (16)	0.0827 (7)
O2B	0.2046 (3)	0.7435 (3)	0.4929 (2)	0.1248 (11)
O3B	0.4211 (3)	0.6657 (3)	0.3590 (3)	0.1424 (13)
O1W	0.6618 (2)	0.4063 (2)	0.33801 (15)	0.0604 (5)
H1WA	0.700 (4)	0.357 (3)	0.393 (2)	0.085*
H1WB	0.590 (4)	0.480 (3)	0.360 (2)	0.085*

	U11	U22	U33	U12	U13	U23
C1	0.0412 (13)	0.0455 (12)	0.0362 (11)	−0.0181 (10)	−0.0109 (10)	−0.0053 (9)
C2	0.0488 (14)	0.0440 (12)	0.0520 (13)	−0.0219 (11)	−0.0156 (11)	−0.0070 (10)
C3	0.0525 (15)	0.0387 (11)	0.0544 (14)	−0.0202 (11)	−0.0157 (12)	−0.0012 (10)
C4	0.0434 (13)	0.0500 (12)	0.0389 (12)	−0.0179 (10)	−0.0133 (10)	−0.0012 (9)
C5	0.0507 (14)	0.0521 (13)	0.0517 (13)	−0.0275 (11)	−0.0170 (11)	−0.0062 (10)
C6	0.0497 (14)	0.0398 (11)	0.0534 (14)	−0.0194 (11)	−0.0160 (11)	−0.0028 (10)
C7	0.0465 (14)	0.0450 (11)	0.0388 (12)	−0.0200 (10)	−0.0124 (10)	−0.0050 (9)
C8	0.0421 (13)	0.0422 (11)	0.0321 (10)	−0.0192 (10)	−0.0123 (9)	−0.0010 (8)
C9	0.0520 (14)	0.0431 (11)	0.0368 (11)	−0.0229 (10)	−0.0174 (10)	0.0035 (9)
C10	0.0562 (16)	0.0611 (14)	0.0407 (13)	−0.0298 (13)	−0.0085 (11)	0.0013 (11)
C11	0.0676 (19)	0.0750 (17)	0.0441 (14)	−0.0310 (14)	0.0027 (13)	−0.0185 (12)
C12	0.083 (2)	0.0551 (14)	0.0554 (16)	−0.0262 (14)	−0.0063 (14)	−0.0210 (12)
C13	0.0628 (16)	0.0480 (12)	0.0462 (13)	−0.0279 (12)	−0.0119 (12)	−0.0061 (10)
C14	0.0546 (15)	0.0547 (13)	0.0428 (13)	−0.0269 (12)	−0.0136 (11)	−0.0029 (10)
C15	0.0750 (19)	0.0539 (14)	0.0577 (15)	−0.0256 (13)	−0.0152 (14)	−0.0155 (12)
C16	0.084 (2)	0.0528 (14)	0.0547 (15)	−0.0323 (14)	−0.0156 (14)	0.0054 (12)
C17	0.069 (2)	0.089 (2)	0.083 (2)	−0.0360 (17)	−0.0439 (17)	0.0046 (16)
N1	0.0405 (11)	0.0428 (10)	0.0328 (10)	−0.0127 (9)	−0.0055 (8)	−0.0034 (7)
O1	0.0619 (11)	0.0625 (10)	0.0681 (11)	−0.0232 (9)	−0.0367 (9)	0.0068 (8)
O2	0.0455 (9)	0.0439 (8)	0.0391 (8)	−0.0175 (7)	−0.0177 (7)	0.0030 (6)
S1B	0.0732 (5)	0.0442 (3)	0.0774 (5)	−0.0137 (3)	−0.0421 (4)	−0.0073 (3)
C1B	0.099 (2)	0.0623 (16)	0.0455 (15)	−0.0356 (17)	−0.0123 (15)	−0.0067 (12)
C2B	0.0573 (17)	0.0531 (14)	0.0662 (18)	−0.0184 (12)	−0.0067 (14)	−0.0182 (13)
C3B	0.0537 (15)	0.0333 (10)	0.0514 (14)	−0.0177 (10)	−0.0181 (11)	−0.0098 (9)
C4B	0.0549 (16)	0.0556 (14)	0.0499 (14)	−0.0169 (12)	−0.0096 (12)	−0.0124 (11)
C5B	0.0560 (17)	0.0624 (16)	0.074 (2)	−0.0098 (13)	−0.0244 (15)	−0.0103 (14)
C6B	0.083 (2)	0.0570 (15)	0.0635 (18)	−0.0200 (15)	−0.0343 (16)	−0.0039 (13)
O1B	0.1121 (18)	0.0715 (12)	0.0969 (16)	−0.0428 (12)	−0.0610 (14)	−0.0056 (11)
O2B	0.127 (2)	0.136 (2)	0.1152 (19)	−0.0817 (19)	−0.0755 (18)	0.0723 (17)
O3B	0.154 (3)	0.0835 (15)	0.183 (3)	0.0502 (15)	−0.122 (2)	−0.0687 (17)
O1W	0.0624 (13)	0.0595 (11)	0.0675 (12)	−0.0208 (9)	−0.0275 (10)	−0.0124 (9)

C1—C2	1.388 (3)	C14—H14A	0.9700
C1—C6	1.390 (3)	C14—H14B	0.9700
C1—C7	1.515 (3)	C15—N1	1.476 (3)
C2—C3	1.375 (3)	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.378 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—N1	1.480 (3)
C4—O1	1.369 (2)	C16—H16A	0.9600
C4—C5	1.378 (3)	C16—H16B	0.9600
C5—C6	1.377 (3)	C16—H16C	0.9600
C5—H5	0.9300	C17—O1	1.412 (3)
C6—H6	0.9300	C17—H17A	0.9600
C7—C14	1.516 (3)	C17—H17B	0.9600
C7—C8	1.559 (3)	C17—H17C	0.9600
C7—H7	0.9800	N1—H1	0.78 (3)
C8—O2	1.441 (2)	O2—H2A	0.81 (2)
C8—C13	1.527 (3)	S1B—O3B	1.405 (2)
C8—C9	1.530 (3)	S1B—O1B	1.4150 (18)
C9—C10	1.509 (3)	S1B—O2B	1.459 (3)
C9—H9A	0.9700	S1B—C3B	1.762 (2)
C9—H9B	0.9700	C1B—C6B	1.352 (4)
C10—C11	1.516 (3)	C1B—C2B	1.378 (4)
C10—H10A	0.9700	C1B—H1B	0.9300
C10—H10B	0.9700	C2B—C3B	1.379 (3)
C11—C12	1.523 (3)	C2B—H2B	0.9300
C11—H11A	0.9700	C3B—C4B	1.377 (3)
C11—H11B	0.9700	C4B—C5B	1.377 (3)
C12—C13	1.526 (4)	C4B—H4B	0.9300
C12—H12A	0.9700	C5B—C6B	1.357 (4)
C12—H12B	0.9700	C5B—H5B	0.9300
C13—H13A	0.9700	C6B—H6B	0.9300
C13—H13B	0.9700	O1W—H1WA	0.88 (3)
C14—N1	1.496 (3)	O1W—H1WB	0.84 (3)
C2—C1—C6	116.87 (19)	H13A—C13—H13B	107.9
C2—C1—C7	120.05 (18)	N1—C14—C7	113.01 (18)
C6—C1—C7	123.08 (18)	N1—C14—H14A	109.0
C3—C2—C1	121.5 (2)	C7—C14—H14A	109.0
C3—C2—H2	119.2	N1—C14—H14B	109.0
C1—C2—H2	119.2	C7—C14—H14B	109.0
C2—C3—C4	120.4 (2)	H14A—C14—H14B	107.8
C2—C3—H3	119.8	N1—C15—H15A	109.5
C4—C3—H3	119.8	N1—C15—H15B	109.5
O1—C4—C5	124.9 (2)	H15A—C15—H15B	109.5
O1—C4—C3	115.6 (2)	N1—C15—H15C	109.5
C5—C4—C3	119.5 (2)	H15A—C15—H15C	109.5
C6—C5—C4	119.51 (19)	H15B—C15—H15C	109.5
C6—C5—H5	120.2	N1—C16—H16A	109.5
C4—C5—H5	120.2	N1—C16—H16B	109.5
C5—C6—C1	122.22 (19)	H16A—C16—H16B	109.5
C5—C6—H6	118.9	N1—C16—H16C	109.5
C1—C6—H6	118.9	H16A—C16—H16C	109.5
C1—C7—C14	110.96 (18)	H16B—C16—H16C	109.5
C1—C7—C8	114.09 (16)	O1—C17—H17A	109.5
C14—C7—C8	112.73 (18)	O1—C17—H17B	109.5
C1—C7—H7	106.1	H17A—C17—H17B	109.5
C14—C7—H7	106.1	O1—C17—H17C	109.5
C8—C7—H7	106.1	H17A—C17—H17C	109.5
O2—C8—C13	105.98 (16)	H17B—C17—H17C	109.5
O2—C8—C9	110.41 (16)	C15—N1—C16	110.07 (18)
C13—C8—C9	109.26 (17)	C15—N1—C14	113.67 (18)
O2—C8—C7	106.88 (15)	C16—N1—C14	110.92 (19)
C13—C8—C7	114.63 (18)	C15—N1—H1	105.9 (18)
C9—C8—C7	109.58 (17)	C16—N1—H1	110.0 (18)
C10—C9—C8	112.83 (18)	C14—N1—H1	106.1 (18)
C10—C9—H9A	109.0	C4—O1—C17	116.91 (19)
C8—C9—H9A	109.0	C8—O2—H2A	108.2 (19)
C10—C9—H9B	109.0	O3B—S1B—O1B	114.29 (16)
C8—C9—H9B	109.0	O3B—S1B—O2B	109.48 (19)
H9A—C9—H9B	107.8	O1B—S1B—O2B	112.99 (15)
C9—C10—C11	111.7 (2)	O3B—S1B—C3B	105.89 (13)
C9—C10—H10A	109.3	O1B—S1B—C3B	107.97 (10)
C11—C10—H10A	109.3	O2B—S1B—C3B	105.58 (12)
C9—C10—H10B	109.3	C6B—C1B—C2B	120.6 (3)
C11—C10—H10B	109.3	C6B—C1B—H1B	119.7
H10A—C10—H10B	107.9	C2B—C1B—H1B	119.7
C10—C11—C12	110.1 (2)	C1B—C2B—C3B	119.8 (3)
C10—C11—H11A	109.6	C1B—C2B—H2B	120.1
C12—C11—H11A	109.6	C3B—C2B—H2B	120.1
C10—C11—H11B	109.6	C4B—C3B—C2B	119.1 (2)
C12—C11—H11B	109.6	C4B—C3B—S1B	120.50 (19)
H11A—C11—H11B	108.1	C2B—C3B—S1B	120.4 (2)
C11—C12—C13	111.7 (2)	C3B—C4B—C5B	119.8 (2)
C11—C12—H12A	109.3	C3B—C4B—H4B	120.1
C13—C12—H12A	109.3	C5B—C4B—H4B	120.1
C11—C12—H12B	109.3	C6B—C5B—C4B	120.5 (3)
C13—C12—H12B	109.3	C6B—C5B—H5B	119.7
H12A—C12—H12B	107.9	C4B—C5B—H5B	119.7
C12—C13—C8	111.8 (2)	C1B—C6B—C5B	120.0 (3)
C12—C13—H13A	109.3	C1B—C6B—H6B	120.0
C8—C13—H13A	109.3	C5B—C6B—H6B	120.0
C12—C13—H13B	109.3	H1WA—O1W—H1WB	102 (3)
C8—C13—H13B	109.3
C6—C1—C2—C3	−1.0 (3)	C10—C11—C12—C13	55.6 (3)
C7—C1—C2—C3	179.1 (2)	C11—C12—C13—C8	−56.5 (3)
C1—C2—C3—C4	0.4 (4)	O2—C8—C13—C12	−64.4 (2)
C2—C3—C4—O1	179.6 (2)	C9—C8—C13—C12	54.5 (2)
C2—C3—C4—C5	0.3 (4)	C7—C8—C13—C12	177.97 (18)
O1—C4—C5—C6	−179.5 (2)	C1—C7—C14—N1	−158.74 (18)
C3—C4—C5—C6	−0.3 (4)	C8—C7—C14—N1	71.9 (2)
C4—C5—C6—C1	−0.4 (4)	C7—C14—N1—C15	74.7 (2)
C2—C1—C6—C5	1.0 (3)	C7—C14—N1—C16	−160.7 (2)
C7—C1—C6—C5	−179.1 (2)	C5—C4—O1—C17	0.4 (4)
C2—C1—C7—C14	134.3 (2)	C3—C4—O1—C17	−178.9 (2)
C6—C1—C7—C14	−45.6 (3)	C6B—C1B—C2B—C3B	0.5 (4)
C2—C1—C7—C8	−97.0 (2)	C1B—C2B—C3B—C4B	−0.4 (4)
C6—C1—C7—C8	83.1 (3)	C1B—C2B—C3B—S1B	179.60 (18)
C1—C7—C8—O2	179.41 (16)	O3B—S1B—C3B—C4B	143.1 (2)
C14—C7—C8—O2	−52.9 (2)	O1B—S1B—C3B—C4B	−94.1 (2)
C1—C7—C8—C13	−63.5 (2)	O2B—S1B—C3B—C4B	27.0 (2)
C14—C7—C8—C13	64.3 (2)	O3B—S1B—C3B—C2B	−36.9 (2)
C1—C7—C8—C9	59.8 (2)	O1B—S1B—C3B—C2B	85.9 (2)
C14—C7—C8—C9	−172.50 (17)	O2B—S1B—C3B—C2B	−153.0 (2)
O2—C8—C9—C10	61.5 (2)	C2B—C3B—C4B—C5B	0.6 (4)
C13—C8—C9—C10	−54.7 (2)	S1B—C3B—C4B—C5B	−179.39 (18)
C7—C8—C9—C10	178.92 (17)	C3B—C4B—C5B—C6B	−1.0 (4)
C8—C9—C10—C11	56.0 (2)	C2B—C1B—C6B—C5B	−0.8 (4)
C9—C10—C11—C12	−55.1 (3)	C4B—C5B—C6B—C1B	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1W	0.81 (3)	1.87 (3)	2.673 (3)	173 (3)
O1W—H1WB···O3B	0.83 (3)	1.92 (3)	2.711 (4)	159 (3)
O1W—H1WA···O2Bi	0.88 (3)	1.91 (3)	2.785 (4)	175 (3)
N1—H1···O2	0.78 (3)	2.05 (3)	2.719 (2)	143 (3)
C15—H15C···O2B	0.96	2.68	3.468 (4)	140
C16—H16A···O1Bii	0.96	2.44	3.395 (4)	172
C2—H2···Cg1	0.93	3.17	3.928	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1W	0.81 (3)	1.87 (3)	2.673 (3)	173 (3)
O1W—H1WB⋯O3B	0.83 (3)	1.92 (3)	2.711 (4)	159 (3)
O1W—H1WA⋯O2B i	0.88 (3)	1.91 (3)	2.785 (4)	175 (3)
N1—H1⋯O2	0.78 (3)	2.05 (3)	2.719 (2)	143 (3)
C15—H15C⋯O2B	0.96	2.68	3.468 (4)	140
C16—H16A⋯O1B ii	0.96	2.44	3.395 (4)	172
C2—H2⋯Cg1	0.93	3.17	3.928	140

Symmetry codes: (i) ; (ii) .