Ethyl 2-(5-cyclo­hexyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811024925

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1871

doi:10.1107/S1600536811024925

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Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 1 June 2011; accepted 24 June 2011; online 2 July 2011)

In the title compound, C₁₉H₂₄O₄S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.875 (4) and 0.125 (4).

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2007a ,b ; 2009 ).

Experimental

Crystal data

C₁₉H₂₄O₄S
M_r = 348.45
Monoclinic, P 2₁ /c
a = 16.1065 (7) Å
b = 4.8485 (2) Å
c = 22.3653 (11) Å
β = 91.010 (2)°
V = 1746.29 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.945, T_max = 0.964
15388 measured reflections
3804 independent reflections
2917 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.132
S = 1.02
3804 reflections
229 parameters
67 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O4Aⁱ	0.99	2.60	3.479 (3)	149
C15—H15B⋯O2ⁱⁱ	0.99	2.56	3.437 (3)	147
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024925/bv2187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024925/bv2187Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024925/bv2187Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a benzofuran moiety have drawn much attention owing to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al. , 2009, Galal et al. , 2009, Khan et al. , 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al. , 2003). As a part of our ongoing study of the substituent effect on the solid state structures of ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues (Choi et al., 2007a,b; 2009), we report herein on the crystal structure of the title compound

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfinyl group (Table 1; C14—H14B···O4Aⁱ), and the second one between an H atom of the benzylic methylene group and the O atom of the carbonyl group (Table 1; C15—H15B···O2ⁱⁱ).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl) acetate derivatives, see: Choi et al. (2007a,b; 2009).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of ethyl 2-(5-cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (298 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 360–361 K; R_f = 0.41 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B).
	Fig. 2. A view of the C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x, y - 1, z; (ii) x, y + 1, z.]

Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₉H₂₄O₄S	F(000) = 744
M_r = 348.45	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3275 reflections
a = 16.1065 (7) Å	θ = 2.2–26.5°
b = 4.8485 (2) Å	µ = 0.21 mm⁻¹
c = 22.3653 (11) Å	T = 173 K
β = 91.010 (2)°	Block, colourless
V = 1746.29 (14) Å³	0.28 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3804 independent reflections
Radiation source: rotating anode	2917 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.049
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.3°
ϕ and ω scans	h = −20→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→6
T_min = 0.945, T_max = 0.964	l = −28→28
15388 measured reflections

Refinement top

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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F²) = 0.132	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0537P)² + 1.3587P] where P = (F_o² + 2F_c²)/3
3804 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.56 e Å⁻³
67 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₉H₂₄O₄S	V = 1746.29 (14) Å³
M_r = 348.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1065 (7) Å	µ = 0.21 mm⁻¹
b = 4.8485 (2) Å	T = 173 K
c = 22.3653 (11) Å	0.28 × 0.20 × 0.18 mm
β = 91.010 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3804 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2917 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.964	R_int = 0.049
15388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	67 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.02	Δρ_max = 0.56 e Å⁻³
3804 reflections	Δρ_min = −0.38 e Å⁻³
229 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.36614 (3)	0.95799 (12)	0.29116 (3)	0.03096 (17)
O1	0.18470 (9)	0.6531 (3)	0.38601 (6)	0.0325 (4)
O2	0.38323 (12)	0.5969 (4)	0.44371 (8)	0.0532 (5)
O3	0.36351 (11)	0.9044 (4)	0.51602 (7)	0.0443 (5)
O4A	0.35467 (11)	1.0448 (4)	0.22886 (8)	0.0392 (6)	0.875 (4)
O4B	0.3933 (9)	1.160 (2)	0.3361 (5)	0.057 (4)	0.125 (4)
C1	0.27598 (12)	0.7963 (4)	0.31809 (9)	0.0266 (5)
C2	0.22021 (12)	0.6069 (4)	0.28840 (9)	0.0253 (4)
C3	0.21169 (12)	0.5003 (4)	0.23082 (9)	0.0262 (5)
H3	0.2479	0.5575	0.2001	0.031*
C4	0.14931 (12)	0.3085 (4)	0.21906 (9)	0.0257 (5)
C5	0.09692 (13)	0.2284 (5)	0.26516 (10)	0.0316 (5)
H5	0.0548	0.0962	0.2567	0.038*
C6	0.10392 (13)	0.3335 (5)	0.32258 (10)	0.0327 (5)
H6	0.0679	0.2773	0.3535	0.039*
C7	0.16600 (13)	0.5242 (5)	0.33243 (9)	0.0283 (5)
C8	0.25217 (13)	0.8178 (5)	0.37491 (10)	0.0297 (5)
C9	0.13521 (13)	0.1884 (4)	0.15724 (9)	0.0269 (5)
H9	0.1225	−0.0119	0.1624	0.032*
C10	0.05931 (13)	0.3205 (5)	0.12640 (9)	0.0308 (5)
H10A	0.0100	0.2924	0.1515	0.037*
H10B	0.0686	0.5216	0.1227	0.037*
C11	0.04212 (14)	0.1998 (6)	0.06457 (10)	0.0379 (6)
H11A	0.0255	0.0042	0.0686	0.045*
H11B	−0.0046	0.3007	0.0453	0.045*
C12	0.11783 (14)	0.2186 (5)	0.02536 (10)	0.0362 (5)
H12A	0.1304	0.4148	0.0173	0.043*
H12B	0.1058	0.1270	−0.0134	0.043*
C13	0.19283 (15)	0.0828 (5)	0.05528 (10)	0.0358 (5)
H13A	0.2420	0.1071	0.0299	0.043*
H13B	0.1825	−0.1175	0.0595	0.043*
C14	0.21039 (13)	0.2080 (5)	0.11680 (9)	0.0317 (5)
H14A	0.2261	0.4041	0.1121	0.038*
H14B	0.2579	0.1106	0.1359	0.038*
C15	0.28665 (14)	0.9685 (5)	0.42765 (10)	0.0338 (5)
H15A	0.2408	1.0187	0.4544	0.041*
H15B	0.3131	1.1413	0.4141	0.041*
C16	0.34984 (14)	0.7987 (5)	0.46210 (10)	0.0347 (5)
C17	0.42421 (19)	0.7598 (7)	0.55380 (13)	0.0591 (8)
H17A	0.4054	0.5687	0.5612	0.071*
H17B	0.4784	0.7519	0.5337	0.071*
C18	0.4327 (2)	0.9083 (9)	0.61010 (14)	0.0775 (11)
H18A	0.4544	1.0937	0.6026	0.116*
H18B	0.4711	0.8088	0.6369	0.116*
H18C	0.3783	0.9225	0.6288	0.116*
C19	0.42883 (14)	0.6559 (5)	0.28894 (12)	0.0403 (6)
H19A	0.4039	0.5228	0.2610	0.060*
H19B	0.4325	0.5739	0.3290	0.060*
H19C	0.4846	0.7046	0.2757	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0292 (3)	0.0237 (3)	0.0402 (3)	−0.0018 (2)	0.0030 (2)	0.0002 (3)
O1	0.0286 (8)	0.0414 (9)	0.0276 (8)	−0.0026 (7)	0.0032 (6)	−0.0066 (7)
O2	0.0576 (12)	0.0484 (11)	0.0531 (11)	0.0198 (10)	−0.0138 (9)	−0.0149 (10)
O3	0.0490 (10)	0.0465 (11)	0.0368 (9)	0.0081 (9)	−0.0149 (8)	−0.0089 (8)
O4A	0.0363 (10)	0.0412 (12)	0.0402 (11)	−0.0020 (9)	0.0010 (8)	0.0072 (9)
O4B	0.058 (9)	0.030 (7)	0.083 (9)	−0.013 (6)	−0.001 (8)	−0.008 (7)
C1	0.0227 (10)	0.0267 (11)	0.0302 (10)	0.0026 (9)	−0.0007 (8)	−0.0023 (9)
C2	0.0211 (9)	0.0254 (11)	0.0294 (10)	0.0025 (9)	0.0000 (8)	−0.0003 (9)
C3	0.0242 (10)	0.0272 (11)	0.0271 (10)	0.0014 (9)	−0.0001 (8)	−0.0002 (9)
C4	0.0251 (10)	0.0253 (11)	0.0266 (10)	0.0027 (9)	−0.0009 (8)	−0.0011 (9)
C5	0.0279 (11)	0.0319 (12)	0.0350 (11)	−0.0035 (10)	−0.0028 (9)	−0.0014 (10)
C6	0.0267 (10)	0.0405 (13)	0.0312 (11)	−0.0049 (10)	0.0050 (9)	−0.0006 (11)
C7	0.0251 (10)	0.0318 (12)	0.0279 (10)	0.0028 (9)	−0.0016 (8)	−0.0043 (10)
C8	0.0245 (10)	0.0308 (12)	0.0336 (11)	−0.0002 (9)	0.0002 (9)	−0.0048 (10)
C9	0.0313 (11)	0.0222 (11)	0.0270 (10)	−0.0006 (9)	−0.0023 (8)	−0.0014 (9)
C10	0.0248 (10)	0.0342 (12)	0.0335 (11)	−0.0021 (10)	−0.0017 (9)	−0.0003 (10)
C11	0.0323 (12)	0.0469 (15)	0.0341 (12)	−0.0067 (11)	−0.0080 (9)	0.0010 (11)
C12	0.0384 (12)	0.0431 (14)	0.0270 (11)	−0.0051 (11)	−0.0041 (9)	−0.0024 (11)
C13	0.0416 (13)	0.0358 (13)	0.0301 (11)	0.0010 (11)	0.0030 (10)	−0.0049 (11)
C14	0.0297 (11)	0.0350 (12)	0.0305 (11)	0.0053 (10)	−0.0016 (9)	−0.0043 (10)
C15	0.0338 (11)	0.0365 (13)	0.0309 (11)	0.0016 (10)	−0.0017 (9)	−0.0073 (10)
C16	0.0322 (12)	0.0371 (13)	0.0346 (12)	−0.0027 (11)	−0.0018 (9)	−0.0044 (11)
C17	0.0637 (18)	0.0570 (18)	0.0557 (17)	0.0124 (16)	−0.0278 (15)	−0.0027 (15)
C18	0.077 (2)	0.102 (3)	0.0525 (18)	0.025 (2)	−0.0274 (16)	−0.0068 (19)
C19	0.0274 (11)	0.0317 (13)	0.0620 (16)	0.0040 (10)	0.0077 (11)	0.0001 (12)

Geometric parameters (Å, º) top

S1—O4B	1.463 (2)	C10—H10A	0.9900
S1—O4A	1.4641 (19)	C10—H10B	0.9900
S1—C1	1.765 (2)	C11—C12	1.517 (3)
S1—C19	1.780 (2)	C11—H11A	0.9900
O1—C8	1.375 (3)	C11—H11B	0.9900
O1—C7	1.380 (2)	C12—C13	1.520 (3)
O2—C16	1.193 (3)	C12—H12A	0.9900
O3—C16	1.325 (3)	C12—H12B	0.9900
O3—C17	1.460 (3)	C13—C14	1.526 (3)
C1—C8	1.338 (3)	C13—H13A	0.9900
C1—C2	1.439 (3)	C13—H13B	0.9900
C2—C7	1.387 (3)	C14—H14A	0.9900
C2—C3	1.392 (3)	C14—H14B	0.9900
C3—C4	1.391 (3)	C15—C16	1.510 (3)
C3—H3	0.9500	C15—H15A	0.9900
C4—C5	1.399 (3)	C15—H15B	0.9900
C4—C9	1.514 (3)	C17—C18	1.455 (4)
C5—C6	1.385 (3)	C17—H17A	0.9900
C5—H5	0.9500	C17—H17B	0.9900
C6—C7	1.377 (3)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C8—C15	1.487 (3)	C18—H18C	0.9800
C9—C14	1.527 (3)	C19—H19A	0.9800
C9—C10	1.533 (3)	C19—H19B	0.9800
C9—H9	1.0000	C19—H19C	0.9800
C10—C11	1.523 (3)

O4B—S1—O4A	119.5 (6)	C10—C11—H11B	109.3
O4B—S1—C1	107.5 (6)	H11A—C11—H11B	108.0
O4A—S1—C1	111.19 (10)	C11—C12—C13	111.10 (19)
O4B—S1—C19	114.0 (6)	C11—C12—H12A	109.4
O4A—S1—C19	105.79 (12)	C13—C12—H12A	109.4
C1—S1—C19	96.58 (11)	C11—C12—H12B	109.4
C8—O1—C7	105.52 (16)	C13—C12—H12B	109.4
C16—O3—C17	116.1 (2)	H12A—C12—H12B	108.0
C8—C1—C2	107.52 (19)	C12—C13—C14	110.96 (19)
C8—C1—S1	122.73 (17)	C12—C13—H13A	109.4
C2—C1—S1	129.54 (16)	C14—C13—H13A	109.4
C7—C2—C3	119.77 (19)	C12—C13—H13B	109.4
C7—C2—C1	104.63 (18)	C14—C13—H13B	109.4
C3—C2—C1	135.6 (2)	H13A—C13—H13B	108.0
C4—C3—C2	118.8 (2)	C13—C14—C9	111.91 (18)
C4—C3—H3	120.6	C13—C14—H14A	109.2
C2—C3—H3	120.6	C9—C14—H14A	109.2
C3—C4—C5	119.3 (2)	C13—C14—H14B	109.2
C3—C4—C9	121.74 (19)	C9—C14—H14B	109.2
C5—C4—C9	118.92 (19)	H14A—C14—H14B	107.9
C6—C5—C4	122.8 (2)	C8—C15—C16	112.1 (2)
C6—C5—H5	118.6	C8—C15—H15A	109.2
C4—C5—H5	118.6	C16—C15—H15A	109.2
C7—C6—C5	116.3 (2)	C8—C15—H15B	109.2
C7—C6—H6	121.9	C16—C15—H15B	109.2
C5—C6—H6	121.9	H15A—C15—H15B	107.9
C6—C7—O1	126.1 (2)	O2—C16—O3	124.2 (2)
C6—C7—C2	123.0 (2)	O2—C16—C15	125.1 (2)
O1—C7—C2	110.79 (18)	O3—C16—C15	110.7 (2)
C1—C8—O1	111.53 (18)	C18—C17—O3	108.3 (2)
C1—C8—C15	133.0 (2)	C18—C17—H17A	110.0
O1—C8—C15	115.31 (19)	O3—C17—H17A	110.0
C4—C9—C14	114.16 (17)	C18—C17—H17B	110.0
C4—C9—C10	110.85 (17)	O3—C17—H17B	110.0
C14—C9—C10	110.00 (18)	H17A—C17—H17B	108.4
C4—C9—H9	107.2	C17—C18—H18A	109.5
C14—C9—H9	107.2	C17—C18—H18B	109.5
C10—C9—H9	107.2	H18A—C18—H18B	109.5
C11—C10—C9	112.27 (19)	C17—C18—H18C	109.5
C11—C10—H10A	109.2	H18A—C18—H18C	109.5
C9—C10—H10A	109.2	H18B—C18—H18C	109.5
C11—C10—H10B	109.2	S1—C19—H19A	109.5
C9—C10—H10B	109.2	S1—C19—H19B	109.5
H10A—C10—H10B	107.9	H19A—C19—H19B	109.5
C12—C11—C10	111.51 (18)	S1—C19—H19C	109.5
C12—C11—H11A	109.3	H19A—C19—H19C	109.5
C10—C11—H11A	109.3	H19B—C19—H19C	109.5
C12—C11—H11B	109.3

O4B—S1—C1—C8	−13.8 (7)	C2—C1—C8—O1	0.8 (2)
O4A—S1—C1—C8	−146.31 (19)	S1—C1—C8—O1	−174.34 (14)
C19—S1—C1—C8	103.9 (2)	C2—C1—C8—C15	176.7 (2)
O4B—S1—C1—C2	172.3 (7)	S1—C1—C8—C15	1.6 (4)
O4A—S1—C1—C2	39.7 (2)	C7—O1—C8—C1	−0.3 (2)
C19—S1—C1—C2	−70.1 (2)	C7—O1—C8—C15	−176.97 (19)
C8—C1—C2—C7	−0.9 (2)	C3—C4—C9—C14	21.3 (3)
S1—C1—C2—C7	173.75 (17)	C5—C4—C9—C14	−160.1 (2)
C8—C1—C2—C3	179.9 (2)	C3—C4—C9—C10	−103.6 (2)
S1—C1—C2—C3	−5.4 (4)	C5—C4—C9—C10	75.0 (2)
C7—C2—C3—C4	−1.0 (3)	C4—C9—C10—C11	−178.72 (18)
C1—C2—C3—C4	178.1 (2)	C14—C9—C10—C11	54.1 (2)
C2—C3—C4—C5	0.1 (3)	C9—C10—C11—C12	−54.8 (3)
C2—C3—C4—C9	178.68 (19)	C10—C11—C12—C13	55.2 (3)
C3—C4—C5—C6	0.5 (3)	C11—C12—C13—C14	−55.9 (3)
C9—C4—C5—C6	−178.2 (2)	C12—C13—C14—C9	56.5 (3)
C4—C5—C6—C7	0.0 (3)	C4—C9—C14—C13	179.72 (18)
C5—C6—C7—O1	−179.3 (2)	C10—C9—C14—C13	−54.9 (2)
C5—C6—C7—C2	−1.0 (3)	C1—C8—C15—C16	−88.6 (3)
C8—O1—C7—C6	178.2 (2)	O1—C8—C15—C16	87.2 (2)
C8—O1—C7—C2	−0.3 (2)	C17—O3—C16—O2	0.5 (4)
C3—C2—C7—C6	1.5 (3)	C17—O3—C16—C15	−179.5 (2)
C1—C2—C7—C6	−177.8 (2)	C8—C15—C16—O2	16.1 (3)
C3—C2—C7—O1	−179.89 (18)	C8—C15—C16—O3	−163.9 (2)
C1—C2—C7—O1	0.8 (2)	C16—O3—C17—C18	178.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O4Aⁱ	0.99	2.60	3.479 (3)	149
C15—H15B···O2ⁱⁱ	0.99	2.56	3.437 (3)	147

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄O₄S
M_r	348.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.1065 (7), 4.8485 (2), 22.3653 (11)
β (°)	91.010 (2)
V (Å³)	1746.29 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.945, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	15388, 3804, 2917
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.132, 1.02
No. of reflections	3804
No. of parameters	229
No. of restraints	67
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O4Aⁱ	0.99	2.60	3.479 (3)	149
C15—H15B···O2ⁱⁱ	0.99	2.56	3.437 (3)	147

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

References

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Volume 67| Part 8| August 2011| Page o1871

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