5-Cyclo­hexyl-2-methyl-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S1600536811018903

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1496

doi:10.1107/S1600536811018903

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5-Cyclohexyl-2-methyl-3-phenylsulfonyl-1-benzofuran

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 10 May 2011; accepted 18 May 2011; online 25 May 2011)

In the title compound, C₂₁H₂₂O₃S, the cyclohexyl ring adopts a chair conformation. The phenyl ring makes a dihedral angle of 78.07 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran moieties, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 3-arylsulfonyl-5-cyclohexyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₂₁H₂₂O₃S
M_r = 354.45
Triclinic, $[P \overline 1]$
a = 9.0424 (2) Å
b = 10.1585 (3) Å
c = 10.3451 (3) Å
α = 90.689 (2)°
β = 109.470 (1)°
γ = 95.634 (2)°
V = 890.59 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.34 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.682, T_max = 0.746
15432 measured reflections
3899 independent reflections
3309 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.05
3899 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O3ⁱ	0.95	2.39	3.284 (2)	157
C11—H11B⋯Cgⁱⁱ	0.99	2.81	3.632 (2)	142
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

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/S1600536811018903/ld2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018903/ld2013Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018903/ld2013Isup3.cml

checkCIF report

Comment top

Recently, compounds involving a benzofuran moiety have attracted much attention owing to their valuable pharmacological properties such as antibacterial, antifungal, antitumor, 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 program of stydying substituent effect on solid state structures of analogues of 3-arylsulfonyl-5-cyclohexyl-2-methyl-1-benzofuran (Choi et al., 2011a,b ), we report herein crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The phenyl ring makes a dihedral angle of 78.07 (5)° with the mean plane of the benzofuran ring. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a phenyl H atom and the O atom of the sulfonyl group (Table; C21—H21···O3ⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C—H···π interactions between a cyclohexyl H atom and the furan ring (Table 1; C11—H11B···Cgⁱⁱ, Cg is the centroid of the C1/C2/C7/O1/C8 furan ring),

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran moieties, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 3-arylsulfonyl-5-cyclohexyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (493 mg, 2.2 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-phenylsulfanyl-1-benzofuran (354 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 430–431 K; R_f = 0.48 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of benzene solution of the title compound 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 atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x + 1, -y, - z + 1; (ii) - x + 1, - y + 1, -z + 1; (iii) - x + 1, - y + 1, - z + 1.]

5-Cyclohexyl-2-methyl-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₂₁H₂₂O₃S	Z = 2
M_r = 354.45	F(000) = 376
Triclinic, P1	D_x = 1.322 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0424 (2) Å	Cell parameters from 6655 reflections
b = 10.1585 (3) Å	θ = 2.4–27.1°
c = 10.3451 (3) Å	µ = 0.20 mm⁻¹
α = 90.689 (2)°	T = 173 K
β = 109.470 (1)°	Block, colourless
γ = 95.634 (2)°	0.34 × 0.23 × 0.18 mm
V = 890.59 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3899 independent reflections
Radiation source: rotating anode	3309 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.0°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
T_min = 0.682, T_max = 0.746	l = −13→13
15432 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0509P)² + 0.3567P] where P = (F_o² + 2F_c²)/3
3899 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₁H₂₂O₃S	γ = 95.634 (2)°
M_r = 354.45	V = 890.59 (4) Å³
Triclinic, P1	Z = 2
a = 9.0424 (2) Å	Mo Kα radiation
b = 10.1585 (3) Å	µ = 0.20 mm⁻¹
c = 10.3451 (3) Å	T = 173 K
α = 90.689 (2)°	0.34 × 0.23 × 0.18 mm
β = 109.470 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3899 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3309 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.746	R_int = 0.031
15432 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
3899 reflections	Δρ_min = −0.45 e Å⁻³
227 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
S1	0.35282 (4)	0.02944 (4)	0.20427 (4)	0.02763 (12)
O1	0.52551 (14)	0.33013 (12)	0.04563 (12)	0.0356 (3)
O2	0.26982 (14)	−0.04640 (12)	0.07882 (12)	0.0372 (3)
O3	0.46616 (13)	−0.03055 (11)	0.31344 (12)	0.0353 (3)
C1	0.44833 (18)	0.17184 (16)	0.16487 (16)	0.0280 (3)
C2	0.55947 (17)	0.26784 (15)	0.26329 (16)	0.0273 (3)
C3	0.62369 (17)	0.28344 (15)	0.40582 (16)	0.0273 (3)
H3	0.5958	0.2194	0.4622	0.033*
C4	0.72944 (18)	0.39460 (16)	0.46415 (17)	0.0293 (3)
C5	0.7685 (2)	0.48740 (17)	0.37830 (19)	0.0357 (4)
H5	0.8407	0.5629	0.4190	0.043*
C6	0.7061 (2)	0.47346 (18)	0.23670 (19)	0.0381 (4)
H6	0.7334	0.5370	0.1796	0.046*
C7	0.60245 (19)	0.36255 (17)	0.18333 (17)	0.0314 (4)
C8	0.43211 (19)	0.21380 (17)	0.03673 (17)	0.0318 (4)
C9	0.79944 (18)	0.41842 (16)	0.61788 (17)	0.0302 (3)
H9	0.8891	0.4900	0.6367	0.036*
C10	0.6804 (2)	0.4677 (2)	0.67798 (19)	0.0441 (5)
H10A	0.6430	0.5497	0.6335	0.053*
H10B	0.5881	0.4001	0.6582	0.053*
C11	0.7530 (2)	0.4957 (2)	0.83250 (19)	0.0461 (5)
H11A	0.8386	0.5695	0.8518	0.055*
H11B	0.6717	0.5232	0.8686	0.055*
C12	0.8189 (2)	0.37507 (19)	0.90467 (18)	0.0385 (4)
H12A	0.7314	0.3045	0.8942	0.046*
H12B	0.8710	0.3980	1.0039	0.046*
C13	0.9367 (2)	0.32409 (17)	0.84674 (17)	0.0349 (4)
H13A	0.9716	0.2415	0.8912	0.042*
H13B	1.0305	0.3903	0.8678	0.042*
C14	0.8662 (2)	0.29686 (17)	0.69219 (17)	0.0332 (4)
H14A	0.7810	0.2227	0.6720	0.040*
H14B	0.9486	0.2697	0.6572	0.040*
C15	0.3387 (2)	0.1631 (2)	−0.10457 (17)	0.0412 (4)
H15A	0.3062	0.0683	−0.1041	0.062*
H15B	0.4030	0.1771	−0.1639	0.062*
H15C	0.2449	0.2104	−0.1393	0.062*
C16	0.21258 (18)	0.08522 (15)	0.27032 (16)	0.0269 (3)
C17	0.06959 (19)	0.11585 (17)	0.17967 (17)	0.0347 (4)
H17	0.0482	0.1080	0.0834	0.042*
C18	−0.0408 (2)	0.1578 (2)	0.2310 (2)	0.0434 (4)
H18	−0.1388	0.1796	0.1700	0.052*
C19	−0.0097 (2)	0.1683 (2)	0.3705 (2)	0.0471 (5)
H19	−0.0865	0.1968	0.4055	0.057*
C20	0.1332 (2)	0.1373 (2)	0.45998 (19)	0.0464 (5)
H20	0.1539	0.1449	0.5562	0.056*
C21	0.2459 (2)	0.09552 (18)	0.41083 (17)	0.0355 (4)
H21	0.3441	0.0743	0.4721	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0291 (2)	0.0271 (2)	0.0247 (2)	0.00455 (15)	0.00598 (15)	0.00047 (15)
O1	0.0392 (6)	0.0417 (7)	0.0311 (6)	0.0062 (5)	0.0180 (5)	0.0068 (5)
O2	0.0424 (7)	0.0356 (6)	0.0303 (6)	0.0008 (5)	0.0090 (5)	−0.0063 (5)
O3	0.0351 (6)	0.0344 (6)	0.0345 (6)	0.0113 (5)	0.0068 (5)	0.0066 (5)
C1	0.0274 (7)	0.0318 (8)	0.0266 (8)	0.0068 (6)	0.0105 (6)	0.0020 (6)
C2	0.0225 (7)	0.0299 (8)	0.0316 (8)	0.0057 (6)	0.0111 (6)	0.0023 (6)
C3	0.0240 (7)	0.0280 (8)	0.0309 (8)	0.0036 (6)	0.0105 (6)	0.0035 (6)
C4	0.0234 (7)	0.0290 (8)	0.0353 (9)	0.0045 (6)	0.0092 (6)	0.0024 (7)
C5	0.0299 (8)	0.0321 (9)	0.0456 (10)	0.0000 (7)	0.0143 (7)	0.0032 (7)
C6	0.0369 (9)	0.0382 (10)	0.0447 (10)	0.0015 (7)	0.0212 (8)	0.0105 (8)
C7	0.0295 (8)	0.0377 (9)	0.0317 (8)	0.0076 (7)	0.0154 (7)	0.0059 (7)
C8	0.0316 (8)	0.0370 (9)	0.0314 (8)	0.0104 (7)	0.0145 (7)	0.0037 (7)
C9	0.0254 (7)	0.0271 (8)	0.0348 (9)	0.0003 (6)	0.0067 (6)	−0.0012 (6)
C10	0.0369 (9)	0.0514 (11)	0.0402 (10)	0.0184 (8)	0.0045 (8)	−0.0088 (8)
C11	0.0431 (10)	0.0510 (12)	0.0413 (10)	0.0178 (9)	0.0073 (8)	−0.0128 (9)
C12	0.0351 (9)	0.0454 (10)	0.0340 (9)	−0.0002 (8)	0.0121 (7)	−0.0078 (8)
C13	0.0326 (8)	0.0365 (9)	0.0349 (9)	0.0074 (7)	0.0096 (7)	0.0015 (7)
C14	0.0356 (8)	0.0330 (9)	0.0332 (9)	0.0091 (7)	0.0131 (7)	0.0006 (7)
C15	0.0493 (10)	0.0493 (11)	0.0268 (9)	0.0113 (9)	0.0133 (8)	0.0026 (8)
C16	0.0272 (7)	0.0249 (7)	0.0273 (8)	0.0008 (6)	0.0077 (6)	0.0024 (6)
C17	0.0333 (8)	0.0392 (9)	0.0279 (8)	0.0057 (7)	0.0047 (7)	0.0026 (7)
C18	0.0315 (9)	0.0501 (11)	0.0448 (11)	0.0116 (8)	0.0060 (8)	−0.0006 (9)
C19	0.0386 (10)	0.0572 (12)	0.0495 (12)	0.0076 (9)	0.0196 (9)	−0.0071 (9)
C20	0.0472 (11)	0.0631 (13)	0.0305 (9)	0.0069 (9)	0.0151 (8)	−0.0052 (9)
C21	0.0340 (9)	0.0424 (10)	0.0269 (8)	0.0041 (7)	0.0058 (7)	0.0013 (7)

Geometric parameters (Å, º) top

S1—O2	1.4333 (12)	C11—C12	1.510 (3)
S1—O3	1.4370 (11)	C11—H11A	0.9900
S1—C1	1.7344 (16)	C11—H11B	0.9900
S1—C16	1.7622 (16)	C12—C13	1.513 (2)
O1—C8	1.367 (2)	C12—H12A	0.9900
O1—C7	1.380 (2)	C12—H12B	0.9900
C1—C8	1.363 (2)	C13—C14	1.521 (2)
C1—C2	1.449 (2)	C13—H13A	0.9900
C2—C7	1.386 (2)	C13—H13B	0.9900
C2—C3	1.394 (2)	C14—H14A	0.9900
C3—C4	1.393 (2)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.402 (2)	C15—H15B	0.9800
C4—C9	1.509 (2)	C15—H15C	0.9800
C5—C6	1.383 (3)	C16—C21	1.383 (2)
C5—H5	0.9500	C16—C17	1.388 (2)
C6—C7	1.373 (2)	C17—C18	1.375 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.479 (2)	C18—C19	1.376 (3)
C9—C14	1.530 (2)	C18—H18	0.9500
C9—C10	1.530 (2)	C19—C20	1.384 (3)
C9—H9	1.0000	C19—H19	0.9500
C10—C11	1.523 (2)	C20—C21	1.379 (3)
C10—H10A	0.9900	C20—H20	0.9500
C10—H10B	0.9900	C21—H21	0.9500

O2—S1—O3	119.24 (7)	C12—C11—H11B	109.3
O2—S1—C1	108.08 (8)	C10—C11—H11B	109.3
O3—S1—C1	107.73 (7)	H11A—C11—H11B	108.0
O2—S1—C16	108.19 (7)	C11—C12—C13	111.29 (15)
O3—S1—C16	107.58 (7)	C11—C12—H12A	109.4
C1—S1—C16	105.18 (7)	C13—C12—H12A	109.4
C8—O1—C7	107.18 (12)	C11—C12—H12B	109.4
C8—C1—C2	107.85 (14)	C13—C12—H12B	109.4
C8—C1—S1	126.38 (13)	H12A—C12—H12B	108.0
C2—C1—S1	125.77 (12)	C12—C13—C14	111.59 (14)
C7—C2—C3	119.42 (15)	C12—C13—H13A	109.3
C7—C2—C1	104.35 (14)	C14—C13—H13A	109.3
C3—C2—C1	136.23 (15)	C12—C13—H13B	109.3
C4—C3—C2	118.86 (15)	C14—C13—H13B	109.3
C4—C3—H3	120.6	H13A—C13—H13B	108.0
C2—C3—H3	120.6	C13—C14—C9	111.94 (14)
C3—C4—C5	119.30 (15)	C13—C14—H14A	109.2
C3—C4—C9	121.16 (14)	C9—C14—H14A	109.2
C5—C4—C9	119.53 (15)	C13—C14—H14B	109.2
C6—C5—C4	122.64 (16)	C9—C14—H14B	109.2
C6—C5—H5	118.7	H14A—C14—H14B	107.9
C4—C5—H5	118.7	C8—C15—H15A	109.5
C7—C6—C5	116.24 (16)	C8—C15—H15B	109.5
C7—C6—H6	121.9	H15A—C15—H15B	109.5
C5—C6—H6	121.9	C8—C15—H15C	109.5
C6—C7—O1	125.78 (15)	H15A—C15—H15C	109.5
C6—C7—C2	123.55 (16)	H15B—C15—H15C	109.5
O1—C7—C2	110.67 (14)	C21—C16—C17	121.39 (16)
C1—C8—O1	109.95 (15)	C21—C16—S1	119.54 (12)
C1—C8—C15	134.96 (17)	C17—C16—S1	119.06 (13)
O1—C8—C15	115.09 (14)	C18—C17—C16	119.13 (16)
C4—C9—C14	113.14 (13)	C18—C17—H17	120.4
C4—C9—C10	111.63 (13)	C16—C17—H17	120.4
C14—C9—C10	109.87 (14)	C17—C18—C19	120.22 (16)
C4—C9—H9	107.3	C17—C18—H18	119.9
C14—C9—H9	107.3	C19—C18—H18	119.9
C10—C9—H9	107.3	C18—C19—C20	120.16 (18)
C11—C10—C9	111.47 (14)	C18—C19—H19	119.9
C11—C10—H10A	109.3	C20—C19—H19	119.9
C9—C10—H10A	109.3	C21—C20—C19	120.64 (17)
C11—C10—H10B	109.3	C21—C20—H20	119.7
C9—C10—H10B	109.3	C19—C20—H20	119.7
H10A—C10—H10B	108.0	C20—C21—C16	118.46 (16)
C12—C11—C10	111.40 (15)	C20—C21—H21	120.8
C12—C11—H11A	109.3	C16—C21—H21	120.8
C10—C11—H11A	109.3

O2—S1—C1—C8	7.74 (17)	C7—O1—C8—C1	−0.16 (17)
O3—S1—C1—C8	137.82 (14)	C7—O1—C8—C15	179.66 (13)
C16—S1—C1—C8	−107.65 (15)	C3—C4—C9—C14	48.8 (2)
O2—S1—C1—C2	−172.58 (12)	C5—C4—C9—C14	−132.76 (16)
O3—S1—C1—C2	−42.50 (15)	C3—C4—C9—C10	−75.79 (19)
C16—S1—C1—C2	72.03 (14)	C5—C4—C9—C10	102.70 (18)
C8—C1—C2—C7	−0.12 (17)	C4—C9—C10—C11	−178.26 (15)
S1—C1—C2—C7	−179.85 (12)	C14—C9—C10—C11	55.4 (2)
C8—C1—C2—C3	179.19 (17)	C9—C10—C11—C12	−56.4 (2)
S1—C1—C2—C3	−0.5 (3)	C10—C11—C12—C13	55.5 (2)
C7—C2—C3—C4	0.2 (2)	C11—C12—C13—C14	−54.8 (2)
C1—C2—C3—C4	−179.04 (16)	C12—C13—C14—C9	55.05 (19)
C2—C3—C4—C5	−0.1 (2)	C4—C9—C14—C13	179.67 (13)
C2—C3—C4—C9	178.41 (13)	C10—C9—C14—C13	−54.83 (18)
C3—C4—C5—C6	0.0 (2)	O2—S1—C16—C21	145.40 (14)
C9—C4—C5—C6	−178.53 (15)	O3—S1—C16—C21	15.35 (15)
C4—C5—C6—C7	0.0 (3)	C1—S1—C16—C21	−99.29 (14)
C5—C6—C7—O1	179.21 (15)	O2—S1—C16—C17	−33.55 (15)
C5—C6—C7—C2	0.2 (3)	O3—S1—C16—C17	−163.60 (13)
C8—O1—C7—C6	−179.08 (16)	C1—S1—C16—C17	81.76 (14)
C8—O1—C7—C2	0.08 (17)	C21—C16—C17—C18	0.2 (3)
C3—C2—C7—C6	−0.3 (2)	S1—C16—C17—C18	179.18 (14)
C1—C2—C7—C6	179.20 (15)	C16—C17—C18—C19	−0.4 (3)
C3—C2—C7—O1	−179.43 (13)	C17—C18—C19—C20	0.3 (3)
C1—C2—C7—O1	0.03 (17)	C18—C19—C20—C21	−0.1 (3)
C2—C1—C8—O1	0.18 (18)	C19—C20—C21—C16	−0.1 (3)
S1—C1—C8—O1	179.90 (11)	C17—C16—C21—C20	0.0 (3)
C2—C1—C8—C15	−179.60 (18)	S1—C16—C21—C20	−178.94 (14)
S1—C1—C8—C15	0.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3ⁱ	0.95	2.39	3.284 (2)	157
C11—H11B···Cgⁱⁱ	0.99	2.81	3.632 (2)	142

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂O₃S
M_r	354.45
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.0424 (2), 10.1585 (3), 10.3451 (3)
α, β, γ (°)	90.689 (2), 109.470 (1), 95.634 (2)
V (Å³)	890.59 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.34 × 0.23 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.682, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15432, 3899, 3309
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.05
No. of reflections	3899
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.45

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

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3ⁱ	0.95	2.39	3.284 (2)	157
C11—H11B···Cgⁱⁱ	0.99	2.81	3.632 (2)	142

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

References

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Volume 67| Part 6| June 2011| Page o1496

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