(R)- and (S)-1-[2-(benz­yloxy)-3-methoxy­phen­yl]-2,2,2-trichloro­ethyl benzene­sulfonate

In the title mol­ecule, C₂₂H₁₉Cl₃O₅S, the meth­oxy group is slightly twisted from the plane of the attached benzene ring by a torsion angle of 18.96 (14)°. In the crystal structure, mol­ecules are linked by inter­molecular C—H...O inter­actions and short Cl...O contacts of 3.0170 (8) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.040
• wR factor = 0.108
• Data-to-parameter ratio = 48.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O4      ..       3.02 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C14    = ...          R

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

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

---

S1. Comment

In our attempt to synthesize new benzimidazole derivatives (Al-Douh et al., 2006a,b), the crystal structure of the title compound, (I), was obtained and determined (Figure 1). Previously, the structure of a 2,2,2-trichloroethyl tosylsulfonate as a functional group has only been determined as an (S) derivative in tosylate (Begley et al., 1978) and as enantiomers in sulfonates (Gill et al., 1979). The research on the physical and chemical properties, including the reaction of the title compound to synthesize biologically important compounds is in progress. We present herein its crystal structure.

The bond lengths and angles in (I) have normal values (Allen et al., 1987) and are comparable with those in the related structures (Begley et al., 1978). The dihedral angle between the benzene rings [(C1—C6) and (C8—C13)] is 22.64 (5)° whereas the torsion angle of C8—O1—C7—C6 is -157.96 (7)°. The methoxy group at C9 is slightly twisted from the plane of the attached benzene ring with torsion angle of C22—O2—C9—C10 = -18.96 (14)°.

The intramolecular C7—H7B···O2 interaction generates an S(6) ring motif, while intramolecular C14—H14A···O1, C14—H14A···O3 and C21—H21A···O3 interaction (Table 1 and Figure 1) generate S(5) ring motifs (Bernstein et al., 1995). In the crystal structure, the molecules are linked by short inter Cl2···O4 ⁱⁱ contact of 3.0170 (8) Å (symmetry code: (ii) -x, -y, -z) into cyclic centrosymmetric R²₂(12) dimers. These dimers are interlinked by the C3—H3A···O2ⁱ (symmetry code: (i) -x, y + 1/2, -z + 1/2) intermolecular interactions.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). For related literature on values of bond lengths and angles, see: Allen et al. (1987). For related structures, see: Al-Douh et al. (2006a,b); Begley et al. (1978); Gill et al. (1979).

S2. Experimental

The title compound (I) was synthesized by adding sulfonyl chloride (535 mg, 3.027 mmol) dropwise to a stirred solution of 2-(2-(benzyloxy)-3-methoxyphenyl)-1H-benzimidazole (1000 mg, 3.027 mmol) in dry dichloromethane (50 ml) and dimethylaminopyridine (370 mg, 3.027 mmol). The resulting solution was stirred at room temperature for 2 hr, then at 320 K for 10 hr. Then, it was cooled to room temperature before removing the solvent by rotary evaporator. Crushed ice (25 g) and CHCl₃ (50 ml) were added to the crude solution. The solution was shaken using separatory funnel and the organic layer was collected. The resulting solution was washed with 10% NaOH (3 × 25 ml) followed by water (3 × 25 ml), brine (3 × 25 ml) and water (3 × 25 ml) again. The organic layer was dried over MgSO₄, filtered and the solvent was removed by rotary evaporator. The crude product was then purified by column chromatography with n-hexane:diethyl ether (1:4). The final product was dissolved in petroleum ether, and single crystals suitable for X-ray diffraction were obtained by evaporation the solvent at room temperature.

S3. Refinement

H atoms were placed in calculated positions and constrained to ride on their carrier atoms, with C—H distances in the range 0.93 - 0.98 Å. The U_iso values were constrained to be 1.5 U_eq of the carrier atom for methyl H atoms and 1.2 U_eq for the remaining H atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed lines indicate intramolecular hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the a axis. The intermolecular C—H···O hydrogen bonds and short inter Cl···O contacts are shown as dashed lines.

(RS)-1-[2-(Benzyloxy)-3-methoxyphenyl]-2,2,2-trichloroethyl benzenesulfonate

Crystal data

C22H19Cl3O5S	F(000) = 1032
Mr = 501.78	Dx = 1.501 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6905 reflections
a = 8.1638 (1) Å	θ = 1.3–40.0°
b = 8.8536 (1) Å	µ = 0.54 mm^−1
c = 30.7221 (5) Å	T = 100 K
β = 90.670 (1)°	Block, brown
V = 2220.41 (5) Å^3	0.48 × 0.30 × 0.29 mm
Z = 4

Data collection

Bruker SMART APEX II CCD area-detector diffractometer	13669 independent reflections
Radiation source: fine-focus sealed tube	11428 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 1.3°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.779, Tmax = 0.858	l = −54→54
122837 measured 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) = 0.108	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.5813P] where P = (Fo^2 + 2Fc^2)/3
13669 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.57 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	0.11494 (3)	−0.07303 (2)	0.165654 (7)	0.01782 (4)
Cl2	0.00495 (3)	−0.10166 (3)	0.076490 (8)	0.02106 (5)
Cl3	0.31730 (3)	−0.22595 (2)	0.103131 (9)	0.02324 (5)
S1	0.29746 (3)	0.21264 (2)	0.024940 (7)	0.01523 (4)
O1	0.22120 (8)	0.28423 (7)	0.17014 (2)	0.01422 (10)
O2	0.46726 (9)	0.36777 (8)	0.22307 (2)	0.01929 (12)
O3	0.17049 (9)	0.30958 (8)	0.04024 (3)	0.02068 (13)
O4	0.28924 (10)	0.14939 (9)	−0.01775 (2)	0.02280 (14)
O5	0.30691 (8)	0.06705 (7)	0.05561 (2)	0.01599 (11)
C1	−0.07517 (13)	0.55311 (13)	0.15528 (4)	0.02359 (18)
H1A	−0.0895	0.5219	0.1266	0.028*
C2	−0.19809 (13)	0.63606 (15)	0.17555 (4)	0.0284 (2)
H2A	−0.2939	0.6600	0.1604	0.034*
C3	−0.17691 (13)	0.68252 (12)	0.21830 (4)	0.02419 (18)
H3A	−0.2575	0.7397	0.2317	0.029*
C4	−0.03532 (12)	0.64364 (11)	0.24112 (3)	0.02053 (15)
H4A	−0.0221	0.6733	0.2700	0.025*
C5	0.08666 (12)	0.56058 (10)	0.22100 (3)	0.01755 (14)
H5A	0.1808	0.5340	0.2365	0.021*
C6	0.06841 (11)	0.51685 (9)	0.17762 (3)	0.01539 (13)
C7	0.20611 (11)	0.43904 (9)	0.15479 (3)	0.01698 (14)
H7A	0.1853	0.4394	0.1236	0.020*
H7B	0.3077	0.4928	0.1604	0.020*
C8	0.37519 (10)	0.22610 (9)	0.16305 (3)	0.01354 (12)
C9	0.50575 (11)	0.26899 (10)	0.19070 (3)	0.01604 (13)
C10	0.66156 (11)	0.21106 (12)	0.18355 (3)	0.02081 (16)
H10A	0.7487	0.2396	0.2015	0.025*
C11	0.68675 (12)	0.11023 (13)	0.14943 (4)	0.02258 (17)
H11A	0.7913	0.0725	0.1446	0.027*
C12	0.55826 (11)	0.06541 (11)	0.12253 (3)	0.01892 (15)
H12A	0.5765	−0.0024	0.1000	0.023*
C13	0.40090 (10)	0.12277 (9)	0.12947 (3)	0.01413 (12)
C14	0.25789 (10)	0.07970 (9)	0.10057 (3)	0.01380 (12)
H14A	0.1740	0.1585	0.1027	0.017*
C15	0.17828 (11)	−0.07436 (9)	0.11099 (3)	0.01580 (13)
C16	0.48763 (10)	0.30045 (10)	0.03280 (3)	0.01484 (12)
C17	0.62592 (12)	0.23099 (11)	0.01579 (3)	0.02071 (16)
H17A	0.6174	0.1392	0.0012	0.025*
C18	0.77654 (12)	0.30144 (14)	0.02105 (4)	0.02500 (19)
H18A	0.8705	0.2563	0.0102	0.030*
C19	0.78741 (12)	0.43929 (13)	0.04253 (3)	0.02332 (18)
H19A	0.8886	0.4867	0.0456	0.028*
C20	0.64852 (13)	0.50693 (11)	0.05949 (3)	0.02105 (16)
H20A	0.6572	0.5987	0.0741	0.025*
C21	0.49626 (11)	0.43739 (10)	0.05464 (3)	0.01730 (14)
H21A	0.4025	0.4818	0.0658	0.021*
C22	0.58060 (14)	0.37768 (13)	0.25894 (4)	0.02435 (18)
H22D	0.5348	0.4396	0.2814	0.037*
H22A	0.6812	0.4217	0.2492	0.037*
H22B	0.6017	0.2784	0.2702	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01973 (9)	0.02031 (9)	0.01344 (8)	−0.00148 (6)	0.00140 (6)	0.00146 (6)
Cl2	0.02243 (9)	0.02403 (10)	0.01665 (9)	−0.00575 (7)	−0.00262 (7)	−0.00215 (7)
Cl3	0.02823 (11)	0.01416 (8)	0.02746 (12)	0.00426 (7)	0.00600 (8)	0.00013 (7)
S1	0.01562 (8)	0.01714 (8)	0.01288 (8)	−0.00106 (6)	−0.00157 (6)	0.00127 (6)
O1	0.0144 (2)	0.0128 (2)	0.0155 (3)	0.00084 (18)	0.00208 (19)	0.00006 (18)
O2	0.0198 (3)	0.0225 (3)	0.0155 (3)	−0.0023 (2)	−0.0018 (2)	−0.0046 (2)
O3	0.0156 (3)	0.0211 (3)	0.0253 (3)	0.0028 (2)	0.0002 (2)	0.0051 (2)
O4	0.0285 (3)	0.0269 (3)	0.0130 (3)	−0.0073 (3)	−0.0038 (2)	0.0000 (2)
O5	0.0213 (3)	0.0150 (2)	0.0118 (2)	0.0006 (2)	0.0021 (2)	−0.00034 (19)
C1	0.0204 (4)	0.0302 (4)	0.0200 (4)	0.0046 (3)	−0.0034 (3)	−0.0051 (3)
C2	0.0185 (4)	0.0368 (5)	0.0298 (5)	0.0079 (4)	−0.0020 (3)	−0.0040 (4)
C3	0.0205 (4)	0.0255 (4)	0.0267 (5)	0.0044 (3)	0.0071 (3)	−0.0024 (4)
C4	0.0240 (4)	0.0204 (4)	0.0173 (4)	0.0002 (3)	0.0061 (3)	−0.0024 (3)
C5	0.0201 (3)	0.0179 (3)	0.0147 (3)	0.0018 (3)	0.0014 (3)	−0.0003 (3)
C6	0.0171 (3)	0.0142 (3)	0.0149 (3)	0.0011 (2)	0.0014 (2)	−0.0009 (2)
C7	0.0208 (3)	0.0141 (3)	0.0162 (3)	0.0024 (2)	0.0039 (3)	0.0014 (2)
C8	0.0134 (3)	0.0141 (3)	0.0131 (3)	0.0005 (2)	0.0010 (2)	0.0001 (2)
C9	0.0160 (3)	0.0177 (3)	0.0144 (3)	−0.0020 (2)	−0.0002 (2)	−0.0002 (3)
C10	0.0149 (3)	0.0277 (4)	0.0198 (4)	−0.0006 (3)	−0.0018 (3)	−0.0005 (3)
C11	0.0149 (3)	0.0304 (4)	0.0224 (4)	0.0045 (3)	0.0002 (3)	−0.0013 (3)
C12	0.0164 (3)	0.0225 (4)	0.0179 (4)	0.0045 (3)	0.0014 (3)	−0.0017 (3)
C13	0.0140 (3)	0.0151 (3)	0.0132 (3)	0.0012 (2)	0.0005 (2)	−0.0001 (2)
C14	0.0157 (3)	0.0137 (3)	0.0119 (3)	0.0009 (2)	0.0006 (2)	−0.0005 (2)
C15	0.0180 (3)	0.0150 (3)	0.0144 (3)	0.0001 (2)	0.0008 (2)	−0.0006 (2)
C16	0.0151 (3)	0.0166 (3)	0.0129 (3)	0.0003 (2)	0.0003 (2)	−0.0002 (2)
C17	0.0181 (3)	0.0229 (4)	0.0211 (4)	0.0028 (3)	0.0017 (3)	−0.0050 (3)
C18	0.0159 (4)	0.0355 (5)	0.0237 (5)	0.0022 (3)	0.0019 (3)	−0.0039 (4)
C19	0.0180 (4)	0.0332 (5)	0.0188 (4)	−0.0057 (3)	−0.0016 (3)	0.0005 (3)
C20	0.0234 (4)	0.0220 (4)	0.0177 (4)	−0.0050 (3)	−0.0010 (3)	−0.0021 (3)
C21	0.0184 (3)	0.0173 (3)	0.0162 (3)	0.0000 (3)	0.0012 (3)	−0.0017 (3)
C22	0.0254 (4)	0.0290 (4)	0.0186 (4)	−0.0060 (3)	−0.0055 (3)	−0.0040 (3)

Geometric parameters (Å, º)

Cl1—C15	1.7631 (9)	C8—C13	1.3964 (12)
Cl2—C15	1.7745 (9)	C8—C9	1.4074 (12)
Cl3—C15	1.7759 (9)	C9—C10	1.3913 (13)
S1—O4	1.4270 (8)	C10—C11	1.3940 (15)
S1—O3	1.4295 (8)	C10—H10A	0.9300
S1—O5	1.5981 (7)	C11—C12	1.3857 (14)
S1—C16	1.7505 (9)	C11—H11A	0.9300
O1—C8	1.3781 (10)	C12—C13	1.4001 (12)
O1—C7	1.4541 (10)	C12—H12A	0.9300
O2—C9	1.3638 (11)	C13—C14	1.5075 (12)
O2—C22	1.4333 (12)	C14—C15	1.5460 (12)
O5—C14	1.4469 (11)	C14—H14A	0.9800
C1—C6	1.3890 (13)	C16—C21	1.3871 (12)
C1—C2	1.3961 (15)	C16—C17	1.3928 (13)
C1—H1A	0.9300	C17—C18	1.3866 (15)
C2—C3	1.3851 (17)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C19	1.3897 (16)
C3—C4	1.3882 (16)	C18—H18A	0.9300
C3—H3A	0.9300	C19—C20	1.3891 (15)
C4—C5	1.3887 (13)	C19—H19A	0.9300
C4—H4A	0.9300	C20—C21	1.3936 (13)
C5—C6	1.3942 (13)	C20—H20A	0.9300
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.4996 (12)	C22—H22D	0.9600
C7—H7A	0.9700	C22—H22A	0.9600
C7—H7B	0.9700	C22—H22B	0.9600
O4—S1—O3	120.76 (5)	C10—C11—H11A	119.5
O4—S1—O5	103.11 (4)	C11—C12—C13	119.66 (9)
O3—S1—O5	108.70 (4)	C11—C12—H12A	120.2
O4—S1—C16	109.46 (4)	C13—C12—H12A	120.2
O3—S1—C16	109.47 (4)	C8—C13—C12	119.76 (8)
O5—S1—C16	103.90 (4)	C8—C13—C14	118.60 (7)
C8—O1—C7	112.01 (7)	C12—C13—C14	121.61 (8)
C9—O2—C22	116.60 (8)	O5—C14—C13	111.16 (7)
C14—O5—S1	119.24 (5)	O5—C14—C15	104.53 (6)
C6—C1—C2	120.53 (10)	C13—C14—C15	115.20 (7)
C6—C1—H1A	119.7	O5—C14—H14A	108.6
C2—C1—H1A	119.7	C13—C14—H14A	108.6
C3—C2—C1	119.79 (10)	C15—C14—H14A	108.6
C3—C2—H2A	120.1	C14—C15—Cl1	108.66 (6)
C1—C2—H2A	120.1	C14—C15—Cl2	109.32 (6)
C2—C3—C4	119.94 (9)	Cl1—C15—Cl2	109.21 (5)
C2—C3—H3A	120.0	C14—C15—Cl3	111.58 (6)
C4—C3—H3A	120.0	Cl1—C15—Cl3	109.24 (5)
C3—C4—C5	120.25 (9)	Cl2—C15—Cl3	108.80 (5)
C3—C4—H4A	119.9	C21—C16—C17	122.05 (8)
C5—C4—H4A	119.9	C21—C16—S1	119.66 (7)
C4—C5—C6	120.21 (9)	C17—C16—S1	118.27 (7)
C4—C5—H5A	119.9	C18—C17—C16	118.63 (9)
C6—C5—H5A	119.9	C18—C17—H17A	120.7
C1—C6—C5	119.23 (8)	C16—C17—H17A	120.7
C1—C6—C7	120.53 (8)	C17—C18—C19	120.14 (9)
C5—C6—C7	120.16 (8)	C17—C18—H18A	119.9
O1—C7—C6	110.03 (7)	C19—C18—H18A	119.9
O1—C7—H7A	109.7	C20—C19—C18	120.58 (9)
C6—C7—H7A	109.7	C20—C19—H19A	119.7
O1—C7—H7B	109.7	C18—C19—H19A	119.7
C6—C7—H7B	109.7	C19—C20—C21	120.03 (9)
H7A—C7—H7B	108.2	C19—C20—H20A	120.0
O1—C8—C13	120.44 (7)	C21—C20—H20A	120.0
O1—C8—C9	119.32 (7)	C16—C21—C20	118.56 (8)
C13—C8—C9	120.22 (8)	C16—C21—H21A	120.7
O2—C9—C10	124.78 (8)	C20—C21—H21A	120.7
O2—C9—C8	115.71 (8)	O2—C22—H22D	109.5
C10—C9—C8	119.51 (8)	O2—C22—H22A	109.5
C9—C10—C11	119.87 (9)	H22D—C22—H22A	109.5
C9—C10—H10A	120.1	O2—C22—H22B	109.5
C11—C10—H10A	120.1	H22D—C22—H22B	109.5
C12—C11—C10	120.97 (9)	H22A—C22—H22B	109.5
C12—C11—H11A	119.5
O4—S1—O5—C14	−157.73 (6)	C9—C8—C13—C14	179.98 (8)
O3—S1—O5—C14	−28.44 (7)	C11—C12—C13—C8	0.85 (14)
C16—S1—O5—C14	88.06 (7)	C11—C12—C13—C14	178.82 (9)
C6—C1—C2—C3	−0.05 (19)	S1—O5—C14—C13	−89.91 (7)
C1—C2—C3—C4	−1.44 (18)	S1—O5—C14—C15	145.20 (6)
C2—C3—C4—C5	1.17 (16)	C8—C13—C14—O5	140.16 (8)
C3—C4—C5—C6	0.59 (15)	C12—C13—C14—O5	−37.83 (11)
C2—C1—C6—C5	1.79 (16)	C8—C13—C14—C15	−101.19 (9)
C2—C1—C6—C7	−174.91 (10)	C12—C13—C14—C15	80.81 (11)
C4—C5—C6—C1	−2.06 (14)	O5—C14—C15—Cl1	179.41 (5)
C4—C5—C6—C7	174.65 (8)	C13—C14—C15—Cl1	57.13 (8)
C8—O1—C7—C6	−157.96 (7)	O5—C14—C15—Cl2	−61.48 (7)
C1—C6—C7—O1	−109.63 (10)	C13—C14—C15—Cl2	176.24 (6)
C5—C6—C7—O1	73.71 (10)	O5—C14—C15—Cl3	58.91 (7)
C7—O1—C8—C13	−104.57 (9)	C13—C14—C15—Cl3	−63.37 (9)
C7—O1—C8—C9	77.03 (10)	O4—S1—C16—C21	139.64 (8)
C22—O2—C9—C10	−18.96 (14)	O3—S1—C16—C21	5.19 (9)
C22—O2—C9—C8	161.48 (8)	O5—S1—C16—C21	−110.77 (7)
O1—C8—C9—O2	−0.15 (12)	O4—S1—C16—C17	−38.88 (9)
C13—C8—C9—O2	−178.55 (8)	O3—S1—C16—C17	−173.33 (8)
O1—C8—C9—C10	−179.73 (8)	O5—S1—C16—C17	70.71 (8)
C13—C8—C9—C10	1.86 (13)	C21—C16—C17—C18	0.15 (15)
O2—C9—C10—C11	179.85 (9)	S1—C16—C17—C18	178.62 (8)
C8—C9—C10—C11	−0.61 (15)	C16—C17—C18—C19	−0.67 (16)
C9—C10—C11—C12	−0.52 (16)	C17—C18—C19—C20	0.96 (17)
C10—C11—C12—C13	0.41 (16)	C18—C19—C20—C21	−0.70 (16)
O1—C8—C13—C12	179.63 (8)	C17—C16—C21—C20	0.11 (14)
C9—C8—C13—C12	−1.98 (13)	S1—C16—C21—C20	−178.35 (7)
O1—C8—C13—C14	1.60 (12)	C19—C20—C21—C16	0.17 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2	0.97	2.56	3.040 (1)	110
C14—H14A···O1	0.98	2.38	2.820 (1)	107
C14—H14A···O3	0.98	2.34	2.838 (1)	111
C21—H21A···O3	0.93	2.55	2.919 (1)	104
C3—H3A···O2^i	0.93	2.49	3.414 (1)	172

Symmetry code: (i) −x, y+1/2, −z+1/2.