3-(3-Fluoro­phenyl­sulfin­yl)-2,4,5,6-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536811032077

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2327

doi:10.1107/S1600536811032077

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3-(3-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-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 4 August 2011; accepted 8 August 2011; online 11 August 2011)

In the title compound, C₁₈H₁₇FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 78.60 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and weak intermolecular C—S⋯π [3.490 (2) Å] interactions.

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 3-(3-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ,b ).

Experimental

Crystal data

C₁₈H₁₇FO₂S
M_r = 316.38
Triclinic, $[P \overline 1]$
a = 8.1631 (13) Å
b = 9.2105 (14) Å
c = 10.9837 (18) Å
α = 93.089 (9)°
β = 104.812 (9)°
γ = 103.368 (9)°
V = 771.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.35 × 0.29 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.926, T_max = 0.944
13358 measured reflections
3851 independent reflections
2949 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.131
S = 1.06
3851 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1ⁱ	0.95	2.51	3.232 (2)	133
C16—H16⋯O2ⁱⁱ	0.95	2.52	3.224 (2)	131
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, 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/S1600536811032077/vm2116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032077/vm2116Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032077/vm2116Isup3.cml

checkCIF report

Comment top

Many compounds containing a benzofuran ring system 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 benzofuran derivatives 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 3-(3-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.018 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 78.60 (5)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a 3-fluorophenyl H atom and the furan O atom (Table 1; C14—H14···O1ⁱ), and the second one between a 3-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C16—H16···O2ⁱⁱ). The crystal packing (Fig. 3) is further stabilized by weak intermolecular C—S···π interactions between the sulfur and 3-fluorophenyl ring, with a C1—S1···Cg^iv [3.490 (2) Å] (Cg is the centroid of the C13–C18 3-fluorophenyl ring).

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 3-(3-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,4,5,6-tetramethyl-1-benzofuran (270 mg, 0.8 mmol) in dichloromethane (30 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 431–432 K; R_f = 0.57 (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 acetone 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.
	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, - y + 1, - z; (ii) x - 1, y, z; (iii) x + 1, y, z.]
	Fig. 3. A view of the C—S···π interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (iv) - x + 1, - y, - z .]

3-(3-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇FO₂S	Z = 2
M_r = 316.38	F(000) = 332
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1631 (13) Å	Cell parameters from 4936 reflections
b = 9.2105 (14) Å	θ = 2.8–27.9°
c = 10.9837 (18) Å	µ = 0.23 mm⁻¹
α = 93.089 (9)°	T = 173 K
β = 104.812 (9)°	Block, colourless
γ = 103.368 (9)°	0.35 × 0.29 × 0.26 mm
V = 771.1 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3851 independent reflections
Radiation source: rotating anode	2949 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.033
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.5°, θ_min = 1.9°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.926, T_max = 0.944	l = −14→14
13358 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0623P)² + 0.2521P] where P = (F_o² + 2F_c²)/3
3851 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₇FO₂S	γ = 103.368 (9)°
M_r = 316.38	V = 771.1 (2) Å³
Triclinic, P1	Z = 2
a = 8.1631 (13) Å	Mo Kα radiation
b = 9.2105 (14) Å	µ = 0.23 mm⁻¹
c = 10.9837 (18) Å	T = 173 K
α = 93.089 (9)°	0.35 × 0.29 × 0.26 mm
β = 104.812 (9)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3851 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2949 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.944	R_int = 0.033
13358 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
3851 reflections	Δρ_min = −0.34 e Å⁻³
203 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	0.72575 (6)	0.17448 (5)	0.11804 (5)	0.03550 (15)
O1	0.79125 (18)	0.60446 (14)	0.10097 (13)	0.0397 (3)
O2	0.84594 (17)	0.11260 (15)	0.21415 (15)	0.0468 (4)
F1	0.2895 (2)	−0.15422 (17)	0.30881 (14)	0.0714 (4)
C1	0.7609 (2)	0.36974 (19)	0.15447 (18)	0.0326 (4)
C2	0.7692 (2)	0.46866 (18)	0.26657 (17)	0.0308 (4)
C3	0.7630 (2)	0.45329 (19)	0.39109 (17)	0.0328 (4)
C4	0.7669 (2)	0.5822 (2)	0.46760 (18)	0.0373 (4)
C5	0.7842 (2)	0.7238 (2)	0.42159 (19)	0.0383 (4)
C6	0.7966 (2)	0.7392 (2)	0.29960 (19)	0.0376 (4)
H6	0.8108	0.8340	0.2681	0.045*
C7	0.7872 (2)	0.6100 (2)	0.22591 (17)	0.0339 (4)
C8	0.7739 (3)	0.4571 (2)	0.06027 (19)	0.0378 (4)
C9	0.7545 (3)	0.3039 (2)	0.44198 (19)	0.0435 (5)
H9A	0.6354	0.2603	0.4472	0.065*
H9B	0.8369	0.3183	0.5267	0.065*
H9C	0.7858	0.2359	0.3851	0.065*
C10	0.7545 (3)	0.5700 (3)	0.6016 (2)	0.0526 (5)
H10A	0.8724	0.5994	0.6605	0.079*
H10B	0.6979	0.4661	0.6090	0.079*
H10C	0.6852	0.6368	0.6222	0.079*
C11	0.7909 (3)	0.8623 (2)	0.5049 (2)	0.0516 (5)
H11A	0.8131	0.9508	0.4601	0.077*
H11B	0.8852	0.8748	0.5835	0.077*
H11C	0.6788	0.8511	0.5251	0.077*
C12	0.7644 (3)	0.4258 (3)	−0.0756 (2)	0.0547 (6)
H12A	0.7929	0.3297	−0.0900	0.082*
H12B	0.8484	0.5064	−0.0988	0.082*
H12C	0.6458	0.4205	−0.1278	0.082*
C13	0.5135 (2)	0.11544 (18)	0.14512 (17)	0.0316 (4)
C14	0.3797 (2)	0.1754 (2)	0.0829 (2)	0.0395 (4)
H14	0.4004	0.2516	0.0297	0.047*
C15	0.2153 (3)	0.1225 (2)	0.0995 (2)	0.0475 (5)
H15	0.1225	0.1637	0.0578	0.057*
C16	0.1836 (3)	0.0112 (2)	0.1754 (2)	0.0467 (5)
H16	0.0703	−0.0248	0.1869	0.056*
C17	0.3193 (3)	−0.0457 (2)	0.23361 (19)	0.0423 (5)
C18	0.4854 (2)	0.0028 (2)	0.22066 (18)	0.0373 (4)
H18	0.5773	−0.0396	0.2621	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0347 (3)	0.0348 (2)	0.0412 (3)	0.01320 (17)	0.0138 (2)	0.00494 (18)
O1	0.0531 (8)	0.0371 (6)	0.0327 (7)	0.0133 (6)	0.0154 (6)	0.0119 (5)
O2	0.0366 (8)	0.0456 (7)	0.0624 (10)	0.0214 (6)	0.0101 (7)	0.0107 (7)
F1	0.0838 (10)	0.0742 (9)	0.0614 (10)	0.0083 (8)	0.0357 (8)	0.0279 (7)
C1	0.0318 (9)	0.0349 (8)	0.0336 (10)	0.0104 (7)	0.0110 (7)	0.0079 (7)
C2	0.0281 (9)	0.0345 (8)	0.0320 (9)	0.0106 (7)	0.0088 (7)	0.0083 (7)
C3	0.0281 (9)	0.0390 (9)	0.0311 (10)	0.0087 (7)	0.0064 (7)	0.0092 (7)
C4	0.0315 (9)	0.0481 (10)	0.0319 (10)	0.0097 (8)	0.0085 (8)	0.0062 (8)
C5	0.0332 (10)	0.0421 (9)	0.0378 (11)	0.0117 (7)	0.0059 (8)	0.0003 (8)
C6	0.0375 (10)	0.0340 (8)	0.0418 (11)	0.0118 (7)	0.0086 (8)	0.0084 (8)
C7	0.0348 (9)	0.0391 (9)	0.0303 (10)	0.0126 (7)	0.0094 (7)	0.0101 (7)
C8	0.0414 (10)	0.0394 (9)	0.0353 (10)	0.0100 (8)	0.0148 (8)	0.0074 (8)
C9	0.0498 (12)	0.0447 (10)	0.0348 (11)	0.0090 (9)	0.0100 (9)	0.0140 (8)
C10	0.0584 (14)	0.0648 (13)	0.0352 (12)	0.0138 (11)	0.0156 (10)	0.0055 (10)
C11	0.0556 (13)	0.0496 (11)	0.0490 (13)	0.0177 (10)	0.0117 (10)	−0.0052 (10)
C12	0.0732 (16)	0.0562 (12)	0.0380 (12)	0.0125 (11)	0.0243 (11)	0.0084 (10)
C13	0.0321 (9)	0.0322 (8)	0.0314 (9)	0.0108 (7)	0.0080 (7)	0.0023 (7)
C14	0.0364 (10)	0.0382 (9)	0.0441 (11)	0.0140 (7)	0.0065 (8)	0.0086 (8)
C15	0.0349 (11)	0.0521 (11)	0.0553 (14)	0.0178 (9)	0.0066 (9)	0.0040 (10)
C16	0.0370 (11)	0.0538 (11)	0.0494 (13)	0.0074 (9)	0.0176 (9)	−0.0037 (10)
C17	0.0529 (12)	0.0418 (10)	0.0329 (10)	0.0066 (8)	0.0181 (9)	0.0045 (8)
C18	0.0417 (11)	0.0391 (9)	0.0332 (10)	0.0147 (8)	0.0092 (8)	0.0080 (8)

Geometric parameters (Å, º) top

S1—O2	1.4818 (14)	C9—H9C	0.9800
S1—C1	1.7613 (17)	C10—H10A	0.9800
S1—C13	1.7975 (18)	C10—H10B	0.9800
O1—C8	1.369 (2)	C10—H10C	0.9800
O1—C7	1.380 (2)	C11—H11A	0.9800
F1—C17	1.349 (2)	C11—H11B	0.9800
C1—C8	1.355 (3)	C11—H11C	0.9800
C1—C2	1.469 (2)	C12—H12A	0.9800
C2—C7	1.387 (2)	C12—H12B	0.9800
C2—C3	1.395 (2)	C12—H12C	0.9800
C3—C4	1.406 (3)	C13—C18	1.378 (3)
C3—C9	1.507 (3)	C13—C14	1.379 (2)
C4—C5	1.414 (3)	C14—C15	1.380 (3)
C4—C10	1.509 (3)	C14—H14	0.9500
C5—C6	1.382 (3)	C15—C16	1.376 (3)
C5—C11	1.511 (3)	C15—H15	0.9500
C6—C7	1.378 (2)	C16—C17	1.362 (3)
C6—H6	0.9500	C16—H16	0.9500
C8—C12	1.484 (3)	C17—C18	1.373 (3)
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800

O2—S1—C1	111.56 (8)	C4—C10—H10B	109.5
O2—S1—C13	106.31 (9)	H10A—C10—H10B	109.5
C1—S1—C13	98.37 (8)	C4—C10—H10C	109.5
C8—O1—C7	106.59 (14)	H10A—C10—H10C	109.5
C8—C1—C2	107.14 (15)	H10B—C10—H10C	109.5
C8—C1—S1	117.83 (14)	C5—C11—H11A	109.5
C2—C1—S1	134.88 (14)	C5—C11—H11B	109.5
C7—C2—C3	119.02 (16)	H11A—C11—H11B	109.5
C7—C2—C1	103.97 (15)	C5—C11—H11C	109.5
C3—C2—C1	137.01 (16)	H11A—C11—H11C	109.5
C2—C3—C4	117.74 (16)	H11B—C11—H11C	109.5
C2—C3—C9	120.95 (16)	C8—C12—H12A	109.5
C4—C3—C9	121.30 (17)	C8—C12—H12B	109.5
C3—C4—C5	121.10 (17)	H12A—C12—H12B	109.5
C3—C4—C10	119.64 (18)	C8—C12—H12C	109.5
C5—C4—C10	119.26 (18)	H12A—C12—H12C	109.5
C6—C5—C4	120.82 (17)	H12B—C12—H12C	109.5
C6—C5—C11	118.33 (18)	C18—C13—C14	121.52 (17)
C4—C5—C11	120.85 (19)	C18—C13—S1	118.72 (14)
C7—C6—C5	116.64 (17)	C14—C13—S1	119.58 (14)
C7—C6—H6	121.7	C13—C14—C15	118.69 (19)
C5—C6—H6	121.7	C13—C14—H14	120.7
C6—C7—O1	124.15 (16)	C15—C14—H14	120.7
C6—C7—C2	124.60 (17)	C16—C15—C14	121.15 (19)
O1—C7—C2	111.23 (15)	C16—C15—H15	119.4
C1—C8—O1	111.06 (16)	C14—C15—H15	119.4
C1—C8—C12	133.92 (18)	C17—C16—C15	118.01 (19)
O1—C8—C12	114.94 (17)	C17—C16—H16	121.0
C3—C9—H9A	109.5	C15—C16—H16	121.0
C3—C9—H9B	109.5	F1—C17—C16	118.40 (19)
H9A—C9—H9B	109.5	F1—C17—C18	118.29 (19)
C3—C9—H9C	109.5	C16—C17—C18	123.3 (2)
H9A—C9—H9C	109.5	C17—C18—C13	117.31 (18)
H9B—C9—H9C	109.5	C17—C18—H18	121.3
C4—C10—H10A	109.5	C13—C18—H18	121.3

O2—S1—C1—C8	132.60 (15)	C8—O1—C7—C2	0.6 (2)
C13—S1—C1—C8	−116.10 (16)	C3—C2—C7—C6	−1.2 (3)
O2—S1—C1—C2	−52.5 (2)	C1—C2—C7—C6	178.53 (17)
C13—S1—C1—C2	58.80 (19)	C3—C2—C7—O1	179.95 (15)
C8—C1—C2—C7	−0.08 (19)	C1—C2—C7—O1	−0.31 (19)
S1—C1—C2—C7	−175.35 (15)	C2—C1—C8—O1	0.4 (2)
C8—C1—C2—C3	179.6 (2)	S1—C1—C8—O1	176.66 (12)
S1—C1—C2—C3	4.3 (3)	C2—C1—C8—C12	−176.0 (2)
C7—C2—C3—C4	3.0 (2)	S1—C1—C8—C12	0.3 (3)
C1—C2—C3—C4	−176.65 (18)	C7—O1—C8—C1	−0.6 (2)
C7—C2—C3—C9	−176.26 (17)	C7—O1—C8—C12	176.51 (17)
C1—C2—C3—C9	4.1 (3)	O2—S1—C13—C18	−14.81 (17)
C2—C3—C4—C5	−2.6 (3)	C1—S1—C13—C18	−130.29 (15)
C9—C3—C4—C5	176.59 (18)	O2—S1—C13—C14	169.93 (14)
C2—C3—C4—C10	178.03 (17)	C1—S1—C13—C14	54.46 (16)
C9—C3—C4—C10	−2.7 (3)	C18—C13—C14—C15	1.3 (3)
C3—C4—C5—C6	0.4 (3)	S1—C13—C14—C15	176.42 (15)
C10—C4—C5—C6	179.75 (18)	C13—C14—C15—C16	−0.6 (3)
C3—C4—C5—C11	−179.15 (17)	C14—C15—C16—C17	−0.2 (3)
C10—C4—C5—C11	0.2 (3)	C15—C16—C17—F1	179.61 (18)
C4—C5—C6—C7	1.4 (3)	C15—C16—C17—C18	0.3 (3)
C11—C5—C6—C7	−179.02 (17)	F1—C17—C18—C13	−178.93 (17)
C5—C6—C7—O1	177.67 (17)	C16—C17—C18—C13	0.4 (3)
C5—C6—C7—C2	−1.0 (3)	C14—C13—C18—C17	−1.2 (3)
C8—O1—C7—C6	−178.27 (17)	S1—C13—C18—C17	−176.35 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.95	2.51	3.232 (2)	133
C16—H16···O2ⁱⁱ	0.95	2.52	3.224 (2)	131

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FO₂S
M_r	316.38
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.1631 (13), 9.2105 (14), 10.9837 (18)
α, β, γ (°)	93.089 (9), 104.812 (9), 103.368 (9)
V (Å³)	771.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.35 × 0.29 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.926, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	13358, 3851, 2949
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.131, 1.06
No. of reflections	3851
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.34

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—H14···O1ⁱ	0.95	2.51	3.232 (2)	133.3
C16—H16···O2ⁱⁱ	0.95	2.52	3.224 (2)	130.9

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

References

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Volume 67| Part 9| September 2011| Page o2327

doi:10.1107/S1600536811032077

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