1-Phenyl-2-phenyl­sulfinyl­cyclo­butan-1-ol

The structure of the title compound, C₁₆H₁₆O₂S, (I), has been determined as part of an investigation into the synthesis of fused carbocyclic ring systems containing a cyclo­butanol ring. Compound (I), a monocyclic example, crystallizes with two mol­ecules in the asymmetric unit. Conformational differences in the phenyl rings on each mol­ecule permit the formation of an infinite chain of intermolecular O—H...O—S hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.047
• wR factor = 0.138
• Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

We have recently shown that a novel cyclization reaction between the lithium enolates of simple ketones and phenyl vinyl sulfoxide provides a simple and convenient route to the preparation of a diverse array of fused carbocyclic ring systems bearing a bridgehead hydroxy group (Loughlin et al., 2002). In the current study, use of the lithium enolate of acetophenone generated the novel monocyclic compound (I). Noteworthy was the formation of (I) as the major cyclobutanol isomer and the novel monoalkylated product 1-phenyl-4-phenylsulfinylbutan-1-one, (II), in a 64:36 ratio from achiral acetophenone and phenyl vinyl sulfoxide, with less than five percent of other products observed.

Compound (I) crystallizes in space group P2₁/c with two molecules, a and b, in the asymmetric unit (Figs. 1a and 1 b). The two molecules are structural isomers with the phenyl groups approximately orthogonal to their corresponding partners. The structure of the cyclobutanol sulfinyl core [OS(C₄H₅)OH] of the two molecules is similar, with relative stereochemistry (1RS_c,2RS_c,RS_s), together with their enantiomers. The bond lengths and angles for this core are similar to those reported for related systems (Loughlin et al., 2002). The cyclobutane rings are distorted from planarity, with C1—C2—C3—C4 - 20.1 (2)° (molecule a) and -18.6 (2)° (molecule b). The O1—C1—C2—S1 torsion angles are 28.9 (3)° (molecule a) and 29.9 (3)° (molecule b).

In the crystal lattice, each molecule forms O—H···O—S hydrogen bonds (Fig. 2) with enantiomers of its partner molecule, generating a hydrogen-bonded chain along the a axis. Interestingly, the molecules along this chain are also linked through edge-to-face C—H···π interactions between the C1 phenyl groups.

S2. Experimental

Compounds (I) and (II) were prepared by the reaction of acetophenone (0.50 g, 0.49 ml, 4.20 mmol) in THF (5 ml) with lithium diisopropylamide (1.7 M, 4.60 mmol, 2.70 ml) in THF (30 ml) at 195 K under nitrogen over 10 min. Rapid addition of phenyl vinyl sulfoxide (0.63 g, 0.56 ml, 4.20 mmol) at 243 K with a 5 min reaction time and workup as described elsewhere (Loughlin et al., 2002) was followed by purification by silica column chromatography (diethyl ether). Fraction 1 (299 mg) contained a 72:28 mixture of unreacted phenylvinyl sulfoxide and (I). Fraction 2 contained (II) (46 mg), m.p. 349–350 K. Suspension of fraction one in ether, filtration and recrystallization (ether) gave (I) as a white solid (m.p. 397–399 K). Crystals of (I) were isolated as colorless plates by slow evaporation of a solution of the pure compound in ether.

S3. Refinement

H atoms were located at calculated positions with C—H set to 0.95 Å. Hydroxyl H atoms on O1 and O3 were located from difference synthesis and O—H was set to 0.95 Å. All H atoms were constrained in the refinement. Due to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.

Computing details

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2001).

Figures

	Fig. 1. ORTEP-3 (Farrugia, 1997) plot shown the atomic atom-numbering scheme for the two molecules in the asymmetric unit of (I). Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The hydrogen-bonding scheme for (I)

1-phenyl-2-phenylsulfinyl-cyclobutan-1-ol

Crystal data

C16H16O2S	F(000) = 1152
Mr = 272.36	Dx = 1.285 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.439 (2) Å	θ = 12.5–16.1°
b = 17.361 (3) Å	µ = 0.23 mm^−1
c = 15.555 (2) Å	T = 295 K
β = 92.74 (1)°	Plate, colorless
V = 2815.8 (7) Å^3	0.50 × 0.20 × 0.20 mm
Z = 8

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.044
Radiation source: Rigaku rotating anode	θmax = 25.0°, θmin = 2.6°
Graphite monochromator	h = −12→7
ω–2θ scans	k = −20→0
6253 measured reflections	l = −18→18
4965 independent reflections	3 standard reflections every 150 reflections
2695 reflections with I > 2σ(I)	intensity decay: 1.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters not refined
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.6926P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4965 reflections	Δρmax = 0.32 e Å^−3
344 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (4)

Special details

Experimental. (1RS_c,2RS_c,RS_s-1-phenyl-2-phenylsulfinylcyclobutan-1-ol (I) (Found: C 70.63, H 5.96, S 11.63%. C₁₆H₁₆O₂S requires C 70.56, H 5.92, S 11.77%); υ_max (KBr)/cm^-1 3424 (m), 1026 (m); δ_H (400 MHz, CDCl₃) 1.91–2.00 (1H, m, H3), 2.42–2.65 (3H, m, H3, 2 x H4), 3.67–3.74 (1H, m, H2), 4.70 (brs, W_h/2 = 15 Hz), 7.18–7.23 (1H, m, p-C₆H₅), 7.25–7.30(2H, m, m-C₆H₅), 7.36–7.40 (2H, m, o-C₆H₅), 7.42–7.47(3H, m, m-,p-C₆H₅S(O)), 7.61–7.67 (2H, m, o-C₆H₅S(O)); δ_C (100 MHz) 17.0 (C3), 34.3 (C4), 66.3 (C2), 80.8 (C1), 124.8 ((o-C₆H₅S(O)), 125.2 (o-C₆H₅), 127.5 (p-C₆H₅), 128.4 (m-C₆H₅), 129.1 (m-C₆H₅S(O)), 131.1 (p-C₆H₅S(O)), 141.6 (i-C₆H₅), 144.5 (i-C₆H₅S(O)); (ESMS +ve) 295 (MNa⁺).

4-phenylsulfinyl-1-phenylbutan-1-one (II) (Found: C 70.44, H 5.94, S 11.56%. C₁₆H₁₆O₂S requires C 70.56, H 5.92, S 11.77%). υ_max (KBr)/cm^-1 1684 (s), 1040 (m); δ_H (400 MHz, CDCl₃) 2.02–2.27 (2H, m, 2 x H3), 2.81–2.99 (2H, m, 2 x H4), 3.13 (ddd, J_2,3 2.5, J_2,3 7.0, J_2,2 9.0 Hz, 2 x H2), 7.39–7.56,(6H, m, m-, p-C₆H₅, m- p-C₆H₅S(O)), 7.58–7.63(2H, m, o-C₆H₅S(O)), 7.86–7.93 (2H, m, o-C₆H₅); δ_C (100 MHz) 17.0 (C3), 36.8 (C2), 56.2 (C4), 124.0 ((o-C₆H₅S(O)), 127.9 (o-C₆H₅), 128.6 (m-C₆H₅), 129.2 (m-C₆H₅S(O)), 131.0 (p-C₆H₅S(O)), 133.3 (p-C₆H₅), 136.5 (i-C₆H₅), 143.6 (i-C₆H₅S(O)), 198.6 (C1); (ESMS +ve) 295 (MNa⁺).

The scan width was (1.63 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
S1A	0.79928 (8)	0.69293 (5)	0.35768 (5)	0.0451 (3)
O1A	0.9664 (2)	0.60198 (13)	0.24917 (13)	0.0487 (8)
O2A	0.6831 (2)	0.64990 (14)	0.38683 (15)	0.0569 (9)
C1A	0.9925 (3)	0.57687 (19)	0.33574 (19)	0.0417 (11)
C2A	0.9366 (3)	0.63804 (19)	0.39665 (19)	0.0411 (10)
C3A	1.0672 (3)	0.6787 (2)	0.3998 (2)	0.0568 (12)
C4A	1.1268 (3)	0.6032 (2)	0.3701 (2)	0.0526 (11)
C5A	0.9555 (3)	0.49321 (19)	0.34484 (19)	0.0437 (11)
C6A	1.0421 (4)	0.4366 (2)	0.3237 (2)	0.0593 (16)
C7A	1.0092 (5)	0.3594 (2)	0.3282 (3)	0.0734 (19)
C8A	0.8898 (6)	0.3386 (2)	0.3537 (3)	0.0792 (18)
C9A	0.8027 (5)	0.3943 (3)	0.3737 (3)	0.0787 (17)
C10A	0.8361 (4)	0.4720 (2)	0.3692 (2)	0.0596 (14)
C11A	0.8245 (3)	0.77323 (19)	0.4281 (2)	0.0434 (11)
C12A	0.8322 (4)	0.7639 (2)	0.5167 (2)	0.0527 (12)
C13A	0.8547 (4)	0.8265 (2)	0.5694 (2)	0.0599 (16)
C14A	0.8696 (4)	0.8985 (2)	0.5330 (3)	0.0604 (16)
C15A	0.8604 (4)	0.9085 (2)	0.4461 (3)	0.0651 (16)
C16A	0.8379 (4)	0.8452 (2)	0.3924 (2)	0.0567 (12)
S1B	0.70971 (9)	0.36215 (5)	0.86351 (5)	0.0491 (3)
O1B	0.5183 (2)	0.37630 (13)	0.72455 (15)	0.0546 (9)
O2B	0.8268 (2)	0.41112 (16)	0.85136 (16)	0.0671 (10)
C1B	0.5077 (3)	0.44483 (18)	0.7724 (2)	0.0405 (11)
C2B	0.5784 (3)	0.42940 (18)	0.8622 (2)	0.0413 (11)
C3B	0.4495 (3)	0.4050 (2)	0.8969 (2)	0.0604 (14)
C4B	0.3823 (3)	0.4473 (2)	0.8204 (2)	0.0514 (11)
C5B	0.5436 (3)	0.5155 (2)	0.7219 (2)	0.0485 (11)
C6B	0.5686 (4)	0.5107 (3)	0.6356 (3)	0.0710 (17)
C7B	0.5966 (5)	0.5763 (4)	0.5891 (4)	0.103 (3)
C8B	0.5992 (5)	0.6469 (4)	0.6291 (6)	0.117 (3)
C9B	0.5757 (5)	0.6532 (3)	0.7147 (5)	0.098 (2)
C10B	0.5478 (4)	0.5875 (2)	0.7614 (3)	0.0668 (17)
C11B	0.7091 (3)	0.33940 (18)	0.9753 (2)	0.0434 (11)
C12B	0.7807 (3)	0.38115 (19)	1.0354 (2)	0.0494 (12)
C13B	0.7755 (4)	0.3624 (3)	1.1214 (2)	0.0675 (16)
C14B	0.6995 (5)	0.3039 (3)	1.1470 (3)	0.0829 (19)
C15B	0.6289 (4)	0.2614 (3)	1.0878 (4)	0.0865 (19)
C16B	0.6344 (4)	0.2780 (2)	1.0010 (3)	0.0669 (14)
H1A	1.03920	0.59270	0.21630	0.0650*
H2A	0.92110	0.61580	0.45090	0.0490*
H6A	1.12470	0.45080	0.30610	0.0710*
H7A	1.06910	0.32100	0.31360	0.0880*
H8A	0.86750	0.28570	0.35750	0.0950*
H9A	0.71980	0.38000	0.39060	0.0940*
H10A	0.77560	0.51040	0.38320	0.0710*
H12A	0.82200	0.71420	0.54100	0.0630*
H13A	0.86000	0.82040	0.63020	0.0720*
H14A	0.88660	0.94160	0.56930	0.0720*
H15A	0.86920	0.95850	0.42230	0.0780*
H16A	0.83200	0.85170	0.33170	0.0680*
H31A	1.07310	0.72020	0.36040	0.0680*
H32A	1.09650	0.69520	0.45560	0.0680*
H41A	1.18740	0.60930	0.32690	0.0630*
H42A	1.16300	0.57240	0.41540	0.0630*
H1B	0.44300	0.37030	0.68720	0.0700*
H2B	0.60580	0.47670	0.88780	0.0500*
H6B	0.56660	0.46200	0.60780	0.0850*
H7B	0.61400	0.57240	0.52990	0.1240*
H8B	0.61750	0.69180	0.59700	0.1400*
H9B	0.57830	0.70220	0.74200	0.1180*
H10B	0.53160	0.59170	0.82080	0.0800*
H12B	0.83320	0.42240	1.01790	0.0590*
H13B	0.82550	0.39070	1.16320	0.0810*
H14B	0.69540	0.29240	1.20650	0.1000*
H15B	0.57620	0.22050	1.10620	0.1040*
H16B	0.58760	0.24780	0.95940	0.0800*
H31B	0.43550	0.35100	0.89740	0.0720*
H32B	0.43260	0.42590	0.95160	0.0720*
H41B	0.31360	0.41920	0.79300	0.0620*
H42B	0.35400	0.49780	0.83340	0.0620*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0455 (5)	0.0509 (5)	0.0382 (4)	0.0043 (4)	−0.0052 (4)	−0.0046 (4)
O1A	0.0484 (14)	0.0635 (16)	0.0347 (12)	0.0043 (12)	0.0058 (10)	0.0055 (10)
O2A	0.0386 (13)	0.0660 (17)	0.0655 (16)	−0.0046 (12)	−0.0025 (11)	−0.0129 (13)
C1A	0.0385 (18)	0.052 (2)	0.0342 (17)	0.0008 (16)	−0.0016 (14)	0.0013 (15)
C2A	0.0422 (18)	0.0464 (19)	0.0343 (16)	0.0010 (16)	−0.0011 (14)	0.0013 (15)
C3A	0.039 (2)	0.062 (2)	0.069 (2)	−0.0055 (19)	−0.0024 (17)	−0.008 (2)
C4A	0.0345 (18)	0.066 (2)	0.057 (2)	−0.0017 (18)	0.0002 (16)	−0.0033 (19)
C5A	0.051 (2)	0.046 (2)	0.0337 (18)	0.0004 (17)	−0.0029 (15)	0.0004 (15)
C6A	0.065 (3)	0.056 (3)	0.057 (2)	0.008 (2)	0.0024 (19)	0.0005 (19)
C7A	0.100 (4)	0.053 (3)	0.066 (3)	0.012 (3)	−0.007 (2)	0.002 (2)
C8A	0.117 (4)	0.045 (2)	0.074 (3)	−0.013 (3)	−0.012 (3)	0.009 (2)
C9A	0.081 (3)	0.065 (3)	0.090 (3)	−0.020 (3)	0.003 (3)	0.014 (2)
C10A	0.061 (3)	0.056 (2)	0.062 (2)	−0.007 (2)	0.004 (2)	0.0079 (19)
C11A	0.0402 (19)	0.043 (2)	0.047 (2)	0.0012 (15)	0.0009 (15)	−0.0056 (16)
C12A	0.065 (2)	0.048 (2)	0.045 (2)	−0.0031 (19)	0.0025 (17)	−0.0042 (17)
C13A	0.068 (3)	0.059 (3)	0.052 (2)	0.007 (2)	−0.0032 (19)	−0.0091 (19)
C14A	0.048 (2)	0.056 (3)	0.076 (3)	0.0064 (19)	−0.008 (2)	−0.020 (2)
C15A	0.067 (3)	0.044 (2)	0.084 (3)	0.008 (2)	0.002 (2)	0.001 (2)
C16A	0.064 (2)	0.052 (2)	0.054 (2)	0.0082 (19)	0.0012 (18)	0.0039 (18)
S1B	0.0480 (5)	0.0545 (6)	0.0446 (5)	0.0140 (5)	0.0009 (4)	−0.0029 (4)
O1B	0.0519 (15)	0.0525 (15)	0.0580 (15)	0.0117 (12)	−0.0134 (12)	−0.0182 (12)
O2B	0.0401 (15)	0.099 (2)	0.0634 (17)	0.0040 (14)	0.0145 (12)	0.0179 (15)
C1B	0.0351 (18)	0.044 (2)	0.0423 (18)	0.0058 (15)	−0.0005 (15)	−0.0068 (15)
C2B	0.0380 (18)	0.0392 (19)	0.0470 (19)	0.0048 (16)	0.0061 (15)	−0.0001 (15)
C3B	0.047 (2)	0.077 (3)	0.058 (2)	0.010 (2)	0.0116 (18)	0.013 (2)
C4B	0.0373 (19)	0.053 (2)	0.064 (2)	0.0012 (17)	0.0041 (17)	−0.0011 (18)
C5B	0.0341 (19)	0.057 (2)	0.054 (2)	0.0048 (17)	−0.0029 (16)	0.0109 (19)
C6B	0.058 (3)	0.096 (3)	0.059 (3)	0.014 (2)	0.004 (2)	0.019 (2)
C7B	0.069 (3)	0.151 (6)	0.092 (4)	0.024 (4)	0.020 (3)	0.066 (4)
C8B	0.049 (3)	0.126 (5)	0.175 (7)	0.011 (3)	0.010 (4)	0.095 (5)
C9B	0.061 (3)	0.057 (3)	0.175 (6)	−0.004 (2)	−0.013 (4)	0.031 (4)
C10B	0.060 (3)	0.055 (3)	0.085 (3)	0.000 (2)	−0.002 (2)	0.011 (2)
C11B	0.0410 (19)	0.041 (2)	0.048 (2)	0.0094 (16)	0.0013 (15)	0.0056 (16)
C12B	0.052 (2)	0.043 (2)	0.053 (2)	0.0064 (17)	−0.0003 (17)	0.0053 (17)
C13B	0.083 (3)	0.067 (3)	0.052 (2)	0.033 (2)	−0.002 (2)	0.000 (2)
C14B	0.082 (3)	0.103 (4)	0.066 (3)	0.040 (3)	0.027 (3)	0.034 (3)
C15B	0.065 (3)	0.081 (3)	0.115 (4)	0.004 (3)	0.020 (3)	0.056 (3)
C16B	0.054 (2)	0.056 (2)	0.090 (3)	−0.006 (2)	−0.005 (2)	0.019 (2)

Geometric parameters (Å, º)

S1A—O2A	1.512 (2)	C12A—H12A	0.9500
S1A—C2A	1.802 (3)	C13A—H13A	0.9506
S1A—C11A	1.785 (3)	C14A—H14A	0.9490
S1B—O2B	1.508 (3)	C15A—H15A	0.9499
S1B—C2B	1.800 (3)	C16A—H16A	0.9500
S1B—C11B	1.783 (3)	C1B—C2B	1.571 (4)
O1A—C1A	1.429 (4)	C1B—C4B	1.538 (4)
O1A—H1A	0.9498	C1B—C5B	1.514 (5)
O1B—C1B	1.411 (4)	C2B—C3B	1.533 (4)
O1B—H1B	0.9605	C3B—C4B	1.539 (5)
C1A—C2A	1.555 (4)	C5B—C6B	1.382 (6)
C1A—C4A	1.545 (4)	C5B—C10B	1.393 (5)
C1A—C5A	1.511 (5)	C6B—C7B	1.388 (8)
C2A—C3A	1.534 (5)	C7B—C8B	1.374 (10)
C3A—C4A	1.532 (5)	C8B—C9B	1.370 (12)
C5A—C6A	1.386 (5)	C9B—C10B	1.391 (7)
C5A—C10A	1.370 (5)	C11B—C16B	1.391 (5)
C6A—C7A	1.386 (5)	C11B—C12B	1.375 (4)
C7A—C8A	1.374 (8)	C12B—C13B	1.380 (5)
C8A—C9A	1.373 (7)	C13B—C14B	1.360 (7)
C9A—C10A	1.396 (6)	C14B—C15B	1.368 (7)
C11A—C12A	1.386 (4)	C15B—C16B	1.384 (8)
C11A—C16A	1.377 (5)	C2B—H2B	0.9507
C12A—C13A	1.375 (5)	C3B—H31B	0.9489
C13A—C14A	1.384 (5)	C3B—H32B	0.9493
C14A—C15A	1.362 (7)	C4B—H41B	0.9512
C15A—C16A	1.393 (5)	C4B—H42B	0.9500
C2A—H2A	0.9489	C6B—H6B	0.9494
C3A—H32A	0.9506	C7B—H7B	0.9495
C3A—H31A	0.9498	C8B—H8B	0.9500
C4A—H42A	0.9486	C9B—H9B	0.9506
C4A—H41A	0.9506	C10B—H10B	0.9500
C6A—H6A	0.9496	C12B—H12B	0.9495
C7A—H7A	0.9490	C13B—H13B	0.9509
C8A—H8A	0.9500	C14B—H14B	0.9498
C9A—H9A	0.9494	C15B—H15B	0.9507
C10A—H10A	0.9507	C16B—H16B	0.9498
S1A···O1A	2.944 (2)	H1A···O2B^iii	1.7915
S1B···O1B	2.883 (2)	H1B···H6B	2.4243
S1A···H1B^i	2.8143	H1B···H41B	2.3380
S1B···H8A^ii	3.0537	H1B···S1A^i	2.8143
S1B···H1A^iii	3.0557	H1B···O2A^i	1.7427
O1A···S1A	2.944 (2)	H1B···H15B^v	2.4846
O1A···C13A^iv	3.226 (4)	H1B···C6B	2.8992
O1A···O2B^iii	2.735 (3)	H2A···C12A	2.9344
O1B···S1B	2.883 (2)	H2A···C10A	2.9201
O1B···O2A^i	2.698 (3)	H2A···H10A	2.5713
O2A···O1B^i	2.698 (3)	H2A···H12A	2.4681
O2B···O1A^iii	2.735 (3)	H2B···C10B	2.7962
O1A···H13A^iv	2.5055	H2B···H10B	2.3654
O1A···H31A	2.8744	H6A···C4A	2.8266
O1B···H15B^v	2.5855	H6B···H1B	2.4243
O1B···H31B	2.8968	H6B···O1B	2.4194
O1B···H6B	2.4194	H7A···H16A^xii	2.5848
O2A···H7B	2.7270	H7A···H12A^iii	2.5564
O2A···H10A	2.6089	H7B···O2A	2.7270
O2A···H1B^i	1.7427	H8A···S1B^v	3.0537
O2B···H1A^iii	1.7915	H8B···H16B^x	2.4737
O2B···H41A^iii	2.7923	H8B···C12A	2.9014
O2B···H15A^vi	2.5476	H8B···H12A	2.3759
O2B···H12B	2.5956	H10A···O2A	2.6089
C3A···C15B^vii	3.479 (5)	H10A···C2A	2.7830
C3A···C14B^vii	3.370 (6)	H10A···H2A	2.5713
C3A···C12A	3.455 (5)	H10B···C14B^ix	3.0776
C3B···C13A^viii	3.518 (5)	H10B···C4B	2.9518
C3B···C14A^viii	3.556 (5)	H10B···H2B	2.3654
C3B···C16B	3.303 (5)	H10B···C2B	2.9262
C7A···C12A^iii	3.572 (6)	H10B···H42B	2.4835
C10B···C14B^ix	3.550 (7)	H12A···C8B	2.9929
C12A···C7A^iii	3.572 (6)	H12A···H2A	2.4681
C12A···C3A	3.455 (5)	H12A···C2A	2.9117
C13A···C3B^x	3.518 (5)	H12A···H8B	2.3759
C13A···O1A^vi	3.226 (4)	H12A···C7A^iii	2.9214
C14A···C3B^x	3.556 (5)	H12A···H7A^iii	2.5564
C14B···C10B^ix	3.550 (7)	H12B···O2B	2.5956
C14B···C3A^xi	3.370 (6)	H12B···H14A^vi	2.5460
C15B···C3A^xi	3.479 (5)	H12B···H15A^vi	2.5848
C16B···C3B	3.303 (5)	H13A···O1A^vi	2.5055
C2A···H12A	2.9117	H14A···H12B^iv	2.5460
C2A···H10A	2.7830	H14B···C8A^xiv	3.0919
C2B···H10B	2.9262	H15A···O2B^iv	2.5476
C4A···H6A	2.8266	H15A···H12B^iv	2.5848
C4B···H10B	2.9518	H15B···O1B^ii	2.5855
C6A···H42A	3.0023	H15B···H1B^ii	2.4846
C6B···H1B	2.8992	H16A···C7A^xv	3.0572
C7A···H16A^xii	3.0572	H16A···H7A^xv	2.5848
C7A···H12A^iii	2.9214	H16B···H31B	2.5524
C8A···H14B^xiii	3.0919	H16B···C8B^viii	2.9171
C8A···H32A^iii	3.0205	H16B···H8B^viii	2.4737
C8B···H12A	2.9929	H31A···O1A	2.8744
C8B···H16B^x	2.9171	H31A···C14B^vii	2.7903
C10A···H2A	2.9201	H31A···C11A	2.9921
C10B···H42B	2.8265	H31A···C13B^vii	2.9377
C10B···H2B	2.7962	H31B···O1B	2.8968
C11A···H31A	2.9921	H31B···H16B	2.5524
C11B···H31B	3.0554	H31B···C11B	3.0554
C12A···H2A	2.9344	H31B···C16B	2.8626
C12A···H8B	2.9014	H32A···C8A^iii	3.0205
C13B···H42B^ix	2.8816	H41A···H1A	2.2763
C13B···H31A^xi	2.9377	H41A···O2B^iii	2.7923
C14B···H10B^ix	3.0776	H41B···H1B	2.3380
C14B···H31A^xi	2.7903	H42A···C6A	3.0023
C16B···H31B	2.8626	H42B···C10B	2.8265
H1A···S1B^iii	3.0557	H42B···H10B	2.4835
H1A···H41A	2.2763	H42B···C13B^ix	2.8816
O2A—S1A—C2A	105.92 (14)	C15A—C14A—H14A	119.50
O2A—S1A—C11A	107.38 (14)	C16A—C15A—H15A	120.25
C2A—S1A—C11A	96.60 (15)	C14A—C15A—H15A	119.99
C2B—S1B—C11B	96.69 (15)	C11A—C16A—H16A	120.37
O2B—S1B—C11B	106.72 (15)	C15A—C16A—H16A	120.21
O2B—S1B—C2B	104.73 (15)	O1B—C1B—C2B	106.3 (2)
C1A—O1A—H1A	109.52	C2B—C1B—C5B	118.8 (3)
C1B—O1B—H1B	109.15	O1B—C1B—C5B	112.5 (3)
C2A—C1A—C5A	119.6 (3)	C4B—C1B—C5B	117.8 (3)
C2A—C1A—C4A	87.0 (2)	S1B—C2B—C3B	119.8 (2)
O1A—C1A—C2A	107.8 (2)	C1B—C2B—C3B	88.7 (2)
O1A—C1A—C5A	110.1 (2)	S1B—C2B—C1B	116.5 (2)
O1A—C1A—C4A	111.4 (2)	C2B—C3B—C4B	88.4 (2)
C4A—C1A—C5A	118.9 (3)	C1B—C4B—C3B	89.7 (2)
S1A—C2A—C3A	117.3 (2)	C1B—C5B—C6B	121.2 (3)
S1A—C2A—C1A	118.1 (2)	C6B—C5B—C10B	118.6 (4)
C1A—C2A—C3A	88.6 (2)	C1B—C5B—C10B	120.1 (3)
C2A—C3A—C4A	88.3 (2)	C5B—C6B—C7B	120.7 (5)
C1A—C4A—C3A	89.0 (2)	C6B—C7B—C8B	119.7 (6)
C1A—C5A—C6A	119.1 (3)	C7B—C8B—C9B	120.7 (6)
C6A—C5A—C10A	119.2 (3)	C8B—C9B—C10B	119.6 (5)
C1A—C5A—C10A	121.6 (3)	C5B—C10B—C9B	120.6 (5)
C5A—C6A—C7A	120.5 (4)	S1B—C11B—C12B	121.3 (2)
C6A—C7A—C8A	119.9 (4)	C12B—C11B—C16B	120.2 (3)
C7A—C8A—C9A	120.0 (4)	S1B—C11B—C16B	118.6 (3)
C8A—C9A—C10A	120.0 (5)	C11B—C12B—C13B	119.3 (3)
C5A—C10A—C9A	120.4 (4)	C12B—C13B—C14B	120.7 (4)
S1A—C11A—C12A	121.3 (3)	C13B—C14B—C15B	120.6 (4)
C12A—C11A—C16A	120.3 (3)	C14B—C15B—C16B	119.9 (4)
S1A—C11A—C16A	118.4 (2)	C11B—C16B—C15B	119.3 (4)
C11A—C12A—C13A	120.0 (3)	S1B—C2B—H2B	109.99
C12A—C13A—C14A	119.3 (3)	C1B—C2B—H2B	110.13
C13A—C14A—C15A	121.1 (3)	C3B—C2B—H2B	110.04
C14A—C15A—C16A	119.8 (3)	C2B—C3B—H31B	114.45
C11A—C16A—C15A	119.4 (3)	C2B—C3B—H32B	114.44
C1A—C2A—H2A	110.41	C4B—C3B—H31B	114.40
C3A—C2A—H2A	110.36	C4B—C3B—H32B	114.42
S1A—C2A—H2A	110.34	H31B—C3B—H32B	109.57
C4A—C3A—H32A	114.56	C1B—C4B—H41B	114.15
C4A—C3A—H31A	114.50	C1B—C4B—H42B	114.18
C2A—C3A—H31A	114.42	C3B—C4B—H41B	114.07
H31A—C3A—H32A	109.43	C3B—C4B—H42B	114.25
C2A—C3A—H32A	114.49	H41B—C4B—H42B	109.46
C1A—C4A—H41A	114.32	C5B—C6B—H6B	119.67
C1A—C4A—H42A	114.38	C7B—C6B—H6B	119.61
C3A—C4A—H41A	114.30	C6B—C7B—H7B	120.12
C3A—C4A—H42A	114.30	C8B—C7B—H7B	120.14
H41A—C4A—H42A	109.45	C7B—C8B—H8B	119.60
C7A—C6A—H6A	119.75	C9B—C8B—H8B	119.69
C5A—C6A—H6A	119.74	C8B—C9B—H9B	120.20
C6A—C7A—H7A	119.96	C10B—C9B—H9B	120.19
C8A—C7A—H7A	120.10	C5B—C10B—H10B	119.65
C7A—C8A—H8A	120.02	C9B—C10B—H10B	119.77
C9A—C8A—H8A	119.99	C11B—C12B—H12B	120.33
C10A—C9A—H9A	119.98	C13B—C12B—H12B	120.38
C8A—C9A—H9A	120.05	C12B—C13B—H13B	119.68
C9A—C10A—H10A	119.73	C14B—C13B—H13B	119.63
C5A—C10A—H10A	119.86	C13B—C14B—H14B	119.76
C11A—C12A—H12A	119.96	C15B—C14B—H14B	119.65
C13A—C12A—H12A	120.00	C14B—C15B—H15B	120.08
C12A—C13A—H13A	120.35	C16B—C15B—H15B	120.04
C14A—C13A—H13A	120.35	C11B—C16B—H16B	120.30
C13A—C14A—H14A	119.35	C15B—C16B—H16B	120.37
O2A—S1A—C2A—C1A	93.1 (3)	C16A—C11A—C12A—C13A	−0.7 (6)
O2A—S1A—C2A—C3A	−162.8 (2)	C12A—C11A—C16A—C15A	0.6 (6)
C11A—S1A—C2A—C1A	−156.7 (2)	S1A—C11A—C16A—C15A	−178.6 (3)
C11A—S1A—C2A—C3A	−52.6 (2)	S1A—C11A—C12A—C13A	178.5 (3)
O2A—S1A—C11A—C12A	52.1 (3)	C11A—C12A—C13A—C14A	−0.1 (6)
O2A—S1A—C11A—C16A	−128.7 (3)	C12A—C13A—C14A—C15A	1.0 (6)
C2A—S1A—C11A—C12A	−56.9 (3)	C13A—C14A—C15A—C16A	−1.2 (6)
C2A—S1A—C11A—C16A	122.3 (3)	C14A—C15A—C16A—C11A	0.4 (6)
O2B—S1B—C2B—C3B	−163.3 (2)	O1B—C1B—C2B—C3B	−93.1 (3)
C2B—S1B—C11B—C12B	−89.6 (3)	C4B—C1B—C2B—S1B	141.7 (2)
O2B—S1B—C2B—C1B	91.9 (2)	O1B—C1B—C2B—S1B	29.9 (3)
O2B—S1B—C11B—C12B	18.0 (3)	C5B—C1B—C4B—C3B	−139.8 (3)
O2B—S1B—C11B—C16B	−161.9 (3)	O1B—C1B—C5B—C6B	7.0 (4)
C11B—S1B—C2B—C3B	−54.0 (3)	O1B—C1B—C5B—C10B	−175.2 (3)
C2B—S1B—C11B—C16B	90.5 (3)	C2B—C1B—C5B—C6B	131.9 (3)
C11B—S1B—C2B—C1B	−158.8 (2)	C2B—C1B—C5B—C10B	−50.2 (4)
C4A—C1A—C2A—S1A	140.4 (2)	C4B—C1B—C5B—C6B	−125.2 (4)
C4A—C1A—C2A—C3A	19.9 (2)	C4B—C1B—C5B—C10B	52.7 (4)
O1A—C1A—C2A—C3A	−91.6 (3)	O1B—C1B—C4B—C3B	87.7 (3)
O1A—C1A—C2A—S1A	28.9 (3)	C2B—C1B—C4B—C3B	−18.6 (2)
C4A—C1A—C5A—C10A	137.8 (3)	C5B—C1B—C2B—S1B	−98.0 (3)
C4A—C1A—C5A—C6A	−45.6 (4)	C5B—C1B—C2B—C3B	139.0 (3)
O1A—C1A—C5A—C6A	84.6 (3)	C4B—C1B—C2B—C3B	18.7 (2)
C5A—C1A—C4A—C3A	−142.4 (3)	C1B—C2B—C3B—C4B	−18.6 (2)
C2A—C1A—C5A—C6A	−149.8 (3)	S1B—C2B—C3B—C4B	−138.7 (2)
C2A—C1A—C5A—C10A	33.6 (4)	C2B—C3B—C4B—C1B	19.1 (2)
O1A—C1A—C5A—C10A	−92.0 (3)	C1B—C5B—C6B—C7B	177.5 (4)
C2A—C1A—C4A—C3A	−19.9 (2)	C10B—C5B—C6B—C7B	−0.4 (6)
C5A—C1A—C2A—S1A	−97.8 (3)	C1B—C5B—C10B—C9B	−177.4 (4)
O1A—C1A—C4A—C3A	88.0 (3)	C6B—C5B—C10B—C9B	0.4 (6)
C5A—C1A—C2A—C3A	141.7 (3)	C5B—C6B—C7B—C8B	−0.2 (7)
C1A—C2A—C3A—C4A	−20.1 (2)	C6B—C7B—C8B—C9B	0.7 (8)
S1A—C2A—C3A—C4A	−141.3 (2)	C7B—C8B—C9B—C10B	−0.6 (8)
C2A—C3A—C4A—C1A	20.2 (2)	C8B—C9B—C10B—C5B	0.0 (7)
C10A—C5A—C6A—C7A	−0.9 (5)	S1B—C11B—C12B—C13B	178.8 (3)
C1A—C5A—C10A—C9A	177.4 (3)	S1B—C11B—C16B—C15B	−177.5 (3)
C1A—C5A—C6A—C7A	−177.5 (3)	C12B—C11B—C16B—C15B	2.6 (5)
C6A—C5A—C10A—C9A	0.8 (5)	C16B—C11B—C12B—C13B	−1.3 (5)
C5A—C6A—C7A—C8A	0.1 (6)	C11B—C12B—C13B—C14B	−0.7 (6)
C6A—C7A—C8A—C9A	0.8 (7)	C12B—C13B—C14B—C15B	1.5 (7)
C7A—C8A—C9A—C10A	−0.8 (7)	C13B—C14B—C15B—C16B	−0.1 (7)
C8A—C9A—C10A—C5A	0.0 (6)	C14B—C15B—C16B—C11B	−1.9 (6)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (v) x, −y+1/2, z−1/2; (vi) x, −y+3/2, z+1/2; (vii) −x+2, y+1/2, −z+3/2; (viii) −x+1, y−1/2, −z+3/2; (ix) −x+1, −y+1, −z+2; (x) −x+1, y+1/2, −z+3/2; (xi) −x+2, y−1/2, −z+3/2; (xii) −x+2, y−1/2, −z+1/2; (xiii) x, y, z−1; (xiv) x, y, z+1; (xv) −x+2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B^iii	0.95	1.79	2.735 (3)	172
O1B—H1B···S1A^i	0.95	2.81	3.697 (2)	153
O1B—H1B···O2A^i	0.95	1.74	2.698 (3)	173
C6B—H6B···O1B	0.95	2.42	2.776 (6)	102
C12B—H12B···O2B	0.95	2.60	2.971 (4)	104
C13A—H13A···O1A^vi	0.95	2.51	3.226 (4)	133
C15A—H15A···O2B^iv	0.95	2.55	3.472 (5)	164
C15B—H15B···O1B^ii	0.95	2.59	3.436 (6)	149

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (vi) x, −y+3/2, z+1/2.