5-Ethyl-3-(3-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811015443

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1278

doi:10.1107/S1600536811015443

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5-Ethyl-3-(3-fluorophenylsulfonyl)-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^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 7 April 2011; accepted 24 April 2011; online 29 April 2011)

In the title compound, C₁₇H₁₅FO₃S, the fluorophenyl ring makes a dihedral angle of 76.11 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by 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 rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For structural studies of related 5-alkyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofurans, see: Choi et al. (2010a ,b ,c ).

Experimental

Crystal data

C₁₇H₁₅FO₃S
M_r = 318.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.4395 (1) Å
b = 11.3701 (2) Å
c = 15.3559 (2) Å
V = 1473.52 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.920, T_max = 0.962
14844 measured reflections
3665 independent reflections
3453 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.077
S = 1.09
3665 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1555 Friedel pairs
Flack parameter: −0.01 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.49	3.206 (2)	133
C13—H13⋯O3ⁱⁱ	0.95	2.51	3.395 (2)	155
C9—H9A⋯Cgⁱⁱⁱ	0.99	2.68	3.625 (2)	159
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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/S1600536811015443/bh2350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015443/bh2350Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015443/bh2350Isup3.cml

checkCIF report

Comment top

Many compounds having a benzofuran skeleton exhibit interesting biological 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 5-alkyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report herein on the molecular and crystal structures of the title compound.

The title compound crystallizes in the non-centrosymmetric space group P2₁2₁2₁ in spite of having no asymmetric C atoms.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 76.11 (5)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfonyl group (Table 1; C6–H6···O2ⁱ), and the second one between a 3-fluorophenyl H atom and the O atom of the sulfonyl (Table 1; C13–H13···O3ⁱⁱ). The crystal packing (Fig. 3) is further stabilized by intermolecular C–H···π interactions between a methylene H atom of the ethyl group and the benzene ring (Table 1; C9–H9A···Cgⁱⁱⁱ, Cg is the centroid of the C2···C7 benzene 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 rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For structural studies of related 5-alkyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofurans, see: Choi et al. (2010a,b,c).

Experimental top

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-ethyl-3-(3-fluorophenylsulfanyl)-2-methyl-1-benzofuran (320 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6 h, 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. 395-396 K; R_f = 0.51 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in diisopropyl ether 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 displacement ellipsoids drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C–H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x+1/2, -y+1, z+1/2; (ii) -x+1, y-1/2, -z+1/2; (iv) -x+1/2, -y+1, z-1/2; (v) -x+1, y+1/2, -z+1/2].
	Fig. 3. A view of the C–H···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (iii) x-1/2, -y+1/2, -z+1; (vi) x+1/2, -y+1/2, -z+1].

5-Ethyl-3-(3-fluorophenylsulfonyl)-2-methyl-1-benzofuran top

Crystal data top

C₁₇H₁₅FO₃S	D_x = 1.435 Mg m⁻³
M_r = 318.35	Melting point: 395 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6176 reflections
a = 8.4395 (1) Å	θ = 2.2–27.6°
b = 11.3701 (2) Å	µ = 0.24 mm⁻¹
c = 15.3559 (2) Å	T = 173 K
V = 1473.52 (4) Å³	Block, colourless
Z = 4	0.35 × 0.25 × 0.16 mm
F(000) = 664

Data collection top

Bruker SMART APEXII CCD diffractometer	3665 independent reflections
Radiation source: rotating anode	3453 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→15
T_min = 0.920, T_max = 0.962	l = −19→20
14844 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0404P)² + 0.1728P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3665 reflections	Δρ_max = 0.23 e Å⁻³
200 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1555 Friedel pairs
0 constraints	Absolute structure parameter: −0.01 (6)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₇H₁₅FO₃S	V = 1473.52 (4) Å³
M_r = 318.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.4395 (1) Å	µ = 0.24 mm⁻¹
b = 11.3701 (2) Å	T = 173 K
c = 15.3559 (2) Å	0.35 × 0.25 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3665 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3453 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.962	R_int = 0.035
14844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.077	Δρ_max = 0.23 e Å⁻³
S = 1.09	Δρ_min = −0.30 e Å⁻³
3665 reflections	Absolute structure: Flack (1983), 1555 Friedel pairs
200 parameters	Absolute structure parameter: −0.01 (6)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.55279 (4)	0.61633 (3)	0.30198 (2)	0.02203 (9)
F1	0.83613 (14)	0.24805 (9)	0.20382 (9)	0.0530 (3)
O1	0.45021 (12)	0.62846 (9)	0.55130 (7)	0.0262 (2)
O2	0.43231 (13)	0.56682 (11)	0.24756 (7)	0.0326 (3)
O3	0.59979 (14)	0.73710 (10)	0.29031 (8)	0.0320 (3)
C1	0.49455 (16)	0.59635 (12)	0.40936 (9)	0.0208 (3)
C2	0.41587 (16)	0.49312 (12)	0.44346 (9)	0.0203 (3)
C3	0.36195 (16)	0.38604 (13)	0.40976 (9)	0.0221 (3)
H3	0.3794	0.3663	0.3504	0.027*
C4	0.28224 (17)	0.30910 (13)	0.46495 (10)	0.0241 (3)
C5	0.25768 (18)	0.34013 (14)	0.55252 (11)	0.0278 (3)
H5	0.2020	0.2870	0.5891	0.033*
C6	0.31114 (19)	0.44473 (15)	0.58750 (11)	0.0278 (3)
H6	0.2944	0.4648	0.6468	0.033*
C7	0.39063 (17)	0.51841 (13)	0.53065 (10)	0.0227 (3)
C8	0.51210 (18)	0.67416 (13)	0.47591 (10)	0.0246 (3)
C9	0.2197 (2)	0.19327 (14)	0.43146 (11)	0.0300 (4)
H9A	0.2258	0.1931	0.3671	0.036*
H9B	0.1066	0.1860	0.4479	0.036*
C10	0.3089 (2)	0.08760 (15)	0.46610 (15)	0.0425 (5)
H10A	0.4204	0.0929	0.4488	0.064*
H10B	0.2625	0.0155	0.4422	0.064*
H10C	0.3016	0.0860	0.5298	0.064*
C11	0.5782 (2)	0.79444 (14)	0.48421 (12)	0.0351 (4)
H11A	0.6645	0.7941	0.5269	0.042*
H11B	0.4949	0.8484	0.5036	0.042*
H11C	0.6191	0.8203	0.4276	0.042*
C12	0.72448 (17)	0.52843 (13)	0.29036 (9)	0.0210 (3)
C13	0.70954 (19)	0.41921 (14)	0.25199 (11)	0.0272 (3)
H13	0.6099	0.3904	0.2327	0.033*
C14	0.8463 (2)	0.35391 (15)	0.24302 (12)	0.0322 (4)
C15	0.9925 (2)	0.39204 (16)	0.27131 (11)	0.0327 (4)
H15	1.0838	0.3439	0.2649	0.039*
C16	1.00295 (19)	0.50192 (15)	0.30918 (11)	0.0312 (3)
H16	1.1028	0.5301	0.3288	0.037*
C17	0.86942 (18)	0.57153 (13)	0.31887 (10)	0.0251 (3)
H17	0.8769	0.6473	0.3445	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02206 (16)	0.02353 (17)	0.02051 (16)	0.00299 (14)	0.00042 (13)	0.00420 (14)
F1	0.0469 (6)	0.0286 (6)	0.0835 (9)	0.0008 (5)	0.0124 (6)	−0.0213 (6)
O1	0.0279 (5)	0.0269 (5)	0.0239 (5)	−0.0037 (5)	0.0046 (4)	−0.0048 (4)
O2	0.0275 (6)	0.0449 (7)	0.0254 (6)	0.0034 (5)	−0.0062 (5)	0.0003 (5)
O3	0.0394 (6)	0.0228 (5)	0.0337 (6)	0.0054 (5)	0.0075 (5)	0.0086 (5)
C1	0.0188 (6)	0.0215 (7)	0.0221 (7)	−0.0002 (5)	0.0015 (5)	0.0002 (5)
C2	0.0174 (6)	0.0217 (7)	0.0218 (7)	0.0023 (5)	0.0003 (5)	0.0016 (5)
C3	0.0209 (6)	0.0237 (7)	0.0216 (7)	0.0011 (6)	−0.0012 (5)	0.0008 (6)
C4	0.0195 (7)	0.0246 (8)	0.0282 (8)	−0.0002 (5)	−0.0018 (6)	0.0039 (6)
C5	0.0241 (8)	0.0310 (8)	0.0282 (8)	−0.0023 (6)	0.0045 (6)	0.0048 (6)
C6	0.0264 (7)	0.0334 (9)	0.0236 (8)	−0.0009 (6)	0.0056 (6)	0.0002 (6)
C7	0.0195 (6)	0.0247 (7)	0.0239 (7)	0.0007 (6)	0.0008 (5)	−0.0026 (6)
C8	0.0223 (7)	0.0266 (8)	0.0250 (7)	−0.0001 (6)	0.0026 (6)	−0.0011 (6)
C9	0.0302 (8)	0.0258 (8)	0.0341 (9)	−0.0071 (6)	−0.0021 (7)	0.0023 (7)
C10	0.0443 (10)	0.0253 (9)	0.0579 (13)	−0.0019 (7)	−0.0031 (9)	0.0033 (8)
C11	0.0406 (9)	0.0279 (8)	0.0368 (9)	−0.0094 (7)	0.0056 (8)	−0.0075 (7)
C12	0.0226 (6)	0.0204 (7)	0.0198 (7)	0.0005 (5)	0.0026 (5)	0.0043 (5)
C13	0.0262 (7)	0.0272 (8)	0.0281 (8)	−0.0038 (6)	0.0031 (6)	−0.0007 (6)
C14	0.0366 (9)	0.0231 (8)	0.0369 (9)	0.0007 (6)	0.0087 (8)	−0.0039 (6)
C15	0.0277 (7)	0.0301 (8)	0.0402 (9)	0.0067 (7)	0.0070 (7)	0.0047 (7)
C16	0.0228 (7)	0.0337 (8)	0.0372 (9)	−0.0014 (6)	−0.0036 (7)	0.0019 (7)
C17	0.0266 (7)	0.0229 (7)	0.0259 (8)	−0.0012 (6)	−0.0003 (6)	0.0008 (6)

Geometric parameters (Å, º) top

S1—O2	1.4315 (12)	C9—C10	1.515 (2)
S1—O3	1.4405 (12)	C9—H9A	0.9900
S1—C1	1.7356 (14)	C9—H9B	0.9900
S1—C12	1.7692 (14)	C10—H10A	0.9800
F1—C14	1.3484 (19)	C10—H10B	0.9800
O1—C8	1.3723 (18)	C10—H10C	0.9800
O1—C7	1.3853 (18)	C11—H11A	0.9800
C1—C8	1.360 (2)	C11—H11B	0.9800
C1—C2	1.4466 (19)	C11—H11C	0.9800
C2—C7	1.386 (2)	C12—C13	1.380 (2)
C2—C3	1.399 (2)	C12—C17	1.389 (2)
C3—C4	1.391 (2)	C13—C14	1.379 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.406 (2)	C14—C15	1.378 (2)
C4—C9	1.509 (2)	C15—C16	1.381 (3)
C5—C6	1.381 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.385 (2)
C6—C7	1.383 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.483 (2)

O2—S1—O3	119.86 (7)	C4—C9—H9B	108.9
O2—S1—C1	107.58 (7)	C10—C9—H9B	108.9
O3—S1—C1	108.72 (7)	H9A—C9—H9B	107.7
O2—S1—C12	107.50 (7)	C9—C10—H10A	109.5
O3—S1—C12	107.48 (7)	C9—C10—H10B	109.5
C1—S1—C12	104.70 (7)	H10A—C10—H10B	109.5
C8—O1—C7	106.68 (12)	C9—C10—H10C	109.5
C8—C1—C2	107.81 (13)	H10A—C10—H10C	109.5
C8—C1—S1	126.72 (12)	H10B—C10—H10C	109.5
C2—C1—S1	125.46 (11)	C8—C11—H11A	109.5
C7—C2—C3	119.21 (13)	C8—C11—H11B	109.5
C7—C2—C1	104.59 (13)	H11A—C11—H11B	109.5
C3—C2—C1	136.17 (14)	C8—C11—H11C	109.5
C4—C3—C2	118.62 (14)	H11A—C11—H11C	109.5
C4—C3—H3	120.7	H11B—C11—H11C	109.5
C2—C3—H3	120.7	C13—C12—C17	122.18 (14)
C3—C4—C5	119.75 (14)	C13—C12—S1	118.45 (12)
C3—C4—C9	120.68 (14)	C17—C12—S1	119.36 (11)
C5—C4—C9	119.56 (14)	C14—C13—C12	116.78 (15)
C6—C5—C4	122.70 (15)	C14—C13—H13	121.6
C6—C5—H5	118.7	C12—C13—H13	121.6
C4—C5—H5	118.7	F1—C14—C15	118.59 (15)
C5—C6—C7	115.76 (15)	F1—C14—C13	118.16 (16)
C5—C6—H6	122.1	C15—C14—C13	123.25 (16)
C7—C6—H6	122.1	C14—C15—C16	118.35 (15)
C6—C7—O1	125.35 (14)	C14—C15—H15	120.8
C6—C7—C2	123.95 (14)	C16—C15—H15	120.8
O1—C7—C2	110.65 (13)	C15—C16—C17	120.67 (15)
C1—C8—O1	110.26 (13)	C15—C16—H16	119.7
C1—C8—C11	134.90 (15)	C17—C16—H16	119.7
O1—C8—C11	114.83 (13)	C16—C17—C12	118.77 (14)
C4—C9—C10	113.49 (14)	C16—C17—H17	120.6
C4—C9—H9A	108.9	C12—C17—H17	120.6
C10—C9—H9A	108.9

O2—S1—C1—C8	−140.71 (14)	C2—C1—C8—O1	0.08 (17)
O3—S1—C1—C8	−9.51 (16)	S1—C1—C8—O1	179.27 (10)
C12—S1—C1—C8	105.13 (15)	C2—C1—C8—C11	−178.45 (17)
O2—S1—C1—C2	38.35 (14)	S1—C1—C8—C11	0.7 (3)
O3—S1—C1—C2	169.55 (12)	C7—O1—C8—C1	−0.53 (16)
C12—S1—C1—C2	−75.81 (13)	C7—O1—C8—C11	178.32 (13)
C8—C1—C2—C7	0.40 (16)	C3—C4—C9—C10	109.92 (17)
S1—C1—C2—C7	−178.81 (11)	C5—C4—C9—C10	−71.0 (2)
C8—C1—C2—C3	178.42 (16)	O2—S1—C12—C13	−14.67 (14)
S1—C1—C2—C3	−0.8 (2)	O3—S1—C12—C13	−144.95 (12)
C7—C2—C3—C4	1.0 (2)	C1—S1—C12—C13	99.55 (13)
C1—C2—C3—C4	−176.79 (15)	O2—S1—C12—C17	164.54 (12)
C2—C3—C4—C5	0.0 (2)	O3—S1—C12—C17	34.25 (14)
C2—C3—C4—C9	179.12 (13)	C1—S1—C12—C17	−81.25 (13)
C3—C4—C5—C6	−0.7 (2)	C17—C12—C13—C14	0.0 (2)
C9—C4—C5—C6	−179.80 (15)	S1—C12—C13—C14	179.16 (13)
C4—C5—C6—C7	0.3 (2)	C12—C13—C14—F1	−178.39 (15)
C5—C6—C7—O1	178.16 (14)	C12—C13—C14—C15	0.9 (3)
C5—C6—C7—C2	0.8 (2)	F1—C14—C15—C16	178.19 (15)
C8—O1—C7—C6	−176.83 (14)	C13—C14—C15—C16	−1.1 (3)
C8—O1—C7—C2	0.81 (16)	C14—C15—C16—C17	0.4 (3)
C3—C2—C7—C6	−1.5 (2)	C15—C16—C17—C12	0.5 (2)
C1—C2—C7—C6	176.93 (14)	C13—C12—C17—C16	−0.7 (2)
C3—C2—C7—O1	−179.17 (11)	S1—C12—C17—C16	−179.84 (12)
C1—C2—C7—O1	−0.74 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.49	3.206 (2)	133
C13—H13···O3ⁱⁱ	0.95	2.51	3.395 (2)	155
C9—H9A···Cgⁱⁱⁱ	0.99	2.68	3.625 (2)	159

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅FO₃S
M_r	318.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	8.4395 (1), 11.3701 (2), 15.3559 (2)
V (Å³)	1473.52 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.35 × 0.25 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.920, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	14844, 3665, 3453
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.077, 1.09
No. of reflections	3665
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.30
Absolute structure	Flack (1983), 1555 Friedel pairs
Absolute structure parameter	−0.01 (6)

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 C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.49	3.206 (2)	133
C13—H13···O3ⁱⁱ	0.95	2.51	3.395 (2)	155
C9—H9A···Cgⁱⁱⁱ	0.99	2.68	3.625 (2)	159

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

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1067. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o1813. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o2575. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 5| May 2011| Page o1278

doi:10.1107/S1600536811015443

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