3-(4-Fluoro­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536810005702

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o643

doi:10.1107/S1600536810005702

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3-(4-Fluorophenylsulfinyl)-2,4,6,7-tetramethyl-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 22 January 2010; accepted 11 February 2010; online 17 February 2010)

In the title compound, C₁₈H₁₇FO₂S, the 4-fluorophenyl ring is almost perpendicular to the benzofuran fragment [88.07 (5)°]. The crystal structure exhibits weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. The molecules form pseudo-helices along the a axis.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 , 2008a ,b ). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ).

Experimental

Crystal data

C₁₈H₁₇FO₂S
M_r = 316.38
Orthorhombic, P n a 2₁
a = 12.0034 (5) Å
b = 19.7455 (7) Å
c = 6.4918 (3) Å
V = 1538.64 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 169 K
0.18 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.644, T_max = 0.746
8107 measured reflections
2280 independent reflections
2175 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.06
2280 reflections
204 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 366 Friedel pairs
Flack parameter: 0.01 (12)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.95	2.59	3.529 (3)	169
C18—H18⋯O2ⁱⁱ	0.95	2.49	3.328 (2)	147
C11—H11A⋯Cgⁱⁱ	0.98	2.66	3.553 (3)	152
C12—H12A⋯Cgⁱⁱⁱ	0.98	2.78	3.590 (3)	141
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) x, y, 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 datablock I. DOI: 10.1107/S1600536810005702/gw2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005702/gw2077Isup2.hkl

checkCIF report

Comment top

Molecules containing benzofuran skeleton display significant biological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2007, 2008a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [88.07 (5)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by two intermolecular C—H···O hydrogen bonds; the first between the 4-fluorophenyl H atom and the furan O atom, with a C15—H15···O1ⁱ, and the second between the 4-fluorophenyl H atom and the oxygen of the S═O unit, with a C18—H18···O2ⁱⁱ, respectively (Table 1).

The title compound is crystallized in the non-centrosymmetric space group Pna2₁ in spite of having no asymmetric C atoms. The space group is caused by a right hand pseudo-helix along the a axis (Fig.3).

The molecular packing (Fig. 3) is further stabilized by two intermolecular C—H···π interactions; the first between the methyl H atom and the 4-fluorophenyl ring, with a C11—H11A···Cgⁱⁱ, the second between the methyl H atom and 4-fluorophenyl ring of an adjacent molecule, with a C12—H12A···Cgⁱⁱⁱ, respectively (Table 1; Cg is the centroid of the C13–C18 4-fluorophenyl ring.)

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007, 2008a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).

Experimental top

77% 3-Chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (360 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 82%, m.p. 437–438 K; R_f = 0.53 (hexane–ethyl acetate, 1:1 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.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1/2, - y + 1/2, z - 1; (ii) x + 1/2 , - y + 1/2, z; (iv) x + 1/2, - y + 1/2, z + 1; (v) x - 1/2, - y + 1/2, z.]
	Fig. 3. C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (ii) x + 1/2, - y + 1/2, z; (iii) x, y, z + 1; (vi) x - 1/2, - y + 1/2, z; (vii) x, y, z - 1.]

3-(4-Fluorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇FO₂S	F(000) = 664
M_r = 316.38	D_x = 1.366 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4518 reflections
a = 12.0034 (5) Å	θ = 2.7–27.4°
b = 19.7455 (7) Å	µ = 0.23 mm⁻¹
c = 6.4918 (3) Å	T = 169 K
V = 1538.64 (11) Å³	Block, colourless
Z = 4	0.18 × 0.17 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2280 independent reflections
Radiation source: Rotating Anode	2175 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics monochromator	R_int = 0.024
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ϕ and ω scans	h = −13→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −25→25
T_min = 0.644, T_max = 0.746	l = −4→8
8107 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) = 0.082	w = 1/[σ²(F_o²) + (0.0551P)² + 0.1527P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2280 reflections	Δρ_max = 0.25 e Å⁻³
204 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 366 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (12)

Crystal data top

C₁₈H₁₇FO₂S	V = 1538.64 (11) Å³
M_r = 316.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.0034 (5) Å	µ = 0.23 mm⁻¹
b = 19.7455 (7) Å	T = 169 K
c = 6.4918 (3) Å	0.18 × 0.17 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2280 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2175 reflections with I > 2σ(I)
T_min = 0.644, T_max = 0.746	R_int = 0.024
8107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.25 e Å⁻³
S = 1.06	Δρ_min = −0.28 e Å⁻³
2280 reflections	Absolute structure: Flack (1983), 366 Friedel pairs
204 parameters	Absolute structure parameter: 0.01 (12)
1 restraint

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
S	0.38790 (4)	0.25971 (2)	0.83129 (12)	0.02606 (12)
F	0.48409 (13)	0.07177 (8)	0.1553 (3)	0.0599 (5)
O1	0.66099 (10)	0.36300 (7)	0.9163 (2)	0.0258 (3)
O2	0.28018 (11)	0.29365 (7)	0.7817 (3)	0.0352 (4)
C1	0.49909 (14)	0.31749 (9)	0.8113 (3)	0.0235 (4)
C2	0.52977 (15)	0.36899 (9)	0.6611 (3)	0.0232 (4)
C3	0.48697 (16)	0.39560 (10)	0.4772 (3)	0.0273 (4)
C4	0.54918 (17)	0.44634 (9)	0.3828 (3)	0.0307 (4)
H4	0.5214	0.4655	0.2587	0.037*
C5	0.65120 (17)	0.47098 (9)	0.4609 (4)	0.0306 (4)
C6	0.69347 (16)	0.44561 (9)	0.6454 (4)	0.0265 (4)
C7	0.62992 (15)	0.39505 (9)	0.7356 (3)	0.0241 (4)
C8	0.57968 (16)	0.31611 (9)	0.9575 (3)	0.0246 (4)
C9	0.38031 (17)	0.37126 (12)	0.3799 (3)	0.0315 (5)
H9A	0.3537	0.4051	0.2812	0.047*
H9B	0.3239	0.3644	0.4871	0.047*
H9C	0.3939	0.3284	0.3081	0.047*
C10	0.71324 (19)	0.52419 (10)	0.3411 (5)	0.0419 (5)
H10A	0.7075	0.5678	0.4126	0.063*
H10B	0.6809	0.5282	0.2031	0.063*
H10C	0.7918	0.5112	0.3297	0.063*
C11	0.80130 (18)	0.46820 (11)	0.7418 (4)	0.0362 (5)
H11A	0.8622	0.4395	0.6920	0.054*
H11B	0.7959	0.4643	0.8920	0.054*
H11C	0.8160	0.5154	0.7043	0.054*
C12	0.59977 (17)	0.27324 (11)	1.1404 (4)	0.0297 (4)
H12A	0.5354	0.2436	1.1630	0.045*
H12B	0.6109	0.3021	1.2615	0.045*
H12C	0.6664	0.2455	1.1179	0.045*
C13	0.42124 (15)	0.20619 (9)	0.6169 (3)	0.0248 (4)
C14	0.33994 (16)	0.19268 (9)	0.4725 (4)	0.0274 (4)
H14	0.2697	0.2146	0.4812	0.033*
C15	0.36070 (16)	0.14697 (9)	0.3142 (4)	0.0311 (4)
H15	0.3059	0.1375	0.2127	0.037*
C16	0.46320 (18)	0.11590 (10)	0.3093 (4)	0.0370 (5)
C17	0.54509 (18)	0.12796 (11)	0.4537 (4)	0.0387 (5)
H17	0.6145	0.1050	0.4460	0.046*
C18	0.52465 (16)	0.17380 (10)	0.6092 (4)	0.0309 (4)
H18	0.5800	0.1832	0.7097	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0189 (2)	0.0315 (2)	0.0278 (2)	−0.00380 (16)	0.0001 (2)	0.0014 (2)
F	0.0513 (8)	0.0624 (9)	0.0659 (11)	0.0177 (7)	−0.0131 (9)	−0.0339 (9)
O1	0.0215 (7)	0.0287 (6)	0.0273 (7)	−0.0043 (5)	−0.0026 (6)	0.0005 (6)
O2	0.0195 (7)	0.0421 (8)	0.0440 (10)	0.0022 (6)	0.0003 (6)	−0.0035 (7)
C1	0.0197 (8)	0.0252 (8)	0.0255 (9)	−0.0019 (6)	0.0007 (8)	−0.0010 (8)
C2	0.0212 (8)	0.0233 (8)	0.0252 (9)	0.0028 (7)	0.0013 (7)	−0.0002 (8)
C3	0.0268 (9)	0.0274 (9)	0.0276 (10)	0.0066 (7)	−0.0018 (8)	−0.0002 (8)
C4	0.0328 (10)	0.0297 (9)	0.0294 (11)	0.0072 (8)	0.0002 (8)	0.0044 (8)
C5	0.0326 (10)	0.0221 (8)	0.0372 (11)	0.0048 (8)	0.0075 (10)	0.0043 (9)
C6	0.0257 (9)	0.0216 (8)	0.0322 (10)	0.0009 (7)	0.0042 (9)	−0.0023 (8)
C7	0.0223 (9)	0.0241 (8)	0.0258 (9)	0.0019 (6)	0.0010 (8)	−0.0015 (8)
C8	0.0211 (9)	0.0263 (9)	0.0263 (9)	−0.0023 (7)	0.0005 (8)	−0.0026 (7)
C9	0.0289 (10)	0.0375 (10)	0.0282 (12)	0.0049 (8)	−0.0065 (8)	0.0007 (8)
C10	0.0422 (11)	0.0345 (10)	0.0490 (13)	0.0003 (9)	0.0082 (13)	0.0131 (12)
C11	0.0327 (11)	0.0328 (10)	0.0431 (12)	−0.0084 (8)	0.0013 (10)	−0.0025 (10)
C12	0.0259 (10)	0.0351 (10)	0.0279 (10)	−0.0026 (8)	−0.0022 (9)	0.0053 (8)
C13	0.0205 (9)	0.0235 (8)	0.0303 (9)	−0.0031 (7)	−0.0028 (8)	0.0019 (8)
C14	0.0212 (9)	0.0268 (8)	0.0342 (10)	−0.0014 (7)	−0.0054 (8)	0.0023 (8)
C15	0.0275 (9)	0.0294 (9)	0.0364 (12)	−0.0023 (7)	−0.0083 (10)	−0.0017 (10)
C16	0.0374 (11)	0.0314 (9)	0.0421 (13)	0.0042 (8)	−0.0050 (11)	−0.0079 (10)
C17	0.0277 (11)	0.0358 (11)	0.0525 (14)	0.0074 (8)	−0.0074 (11)	−0.0071 (11)
C18	0.0228 (9)	0.0297 (9)	0.0403 (11)	0.0010 (8)	−0.0071 (9)	0.0002 (9)

Geometric parameters (Å, º) top

S—O2	1.4915 (14)	C9—H9C	0.9800
S—C1	1.7606 (18)	C10—H10A	0.9800
S—C13	1.793 (2)	C10—H10B	0.9800
F—C16	1.350 (3)	C10—H10C	0.9800
O1—C8	1.372 (2)	C11—H11A	0.9800
O1—C7	1.384 (2)	C11—H11B	0.9800
C1—C8	1.356 (3)	C11—H11C	0.9800
C1—C2	1.456 (3)	C12—H12A	0.9800
C2—C7	1.394 (3)	C12—H12B	0.9800
C2—C3	1.402 (3)	C12—H12C	0.9800
C3—C4	1.392 (3)	C13—C14	1.379 (3)
C3—C9	1.506 (3)	C13—C18	1.397 (3)
C4—C5	1.412 (3)	C14—C15	1.390 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.394 (3)	C15—C16	1.375 (3)
C5—C10	1.504 (3)	C15—H15	0.9500
C6—C7	1.386 (3)	C16—C17	1.379 (3)
C6—C11	1.505 (3)	C17—C18	1.378 (3)
C8—C12	1.478 (3)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800

O2—S—C1	110.49 (9)	C5—C10—H10B	109.5
O2—S—C13	106.91 (10)	H10A—C10—H10B	109.5
C1—S—C13	98.95 (9)	C5—C10—H10C	109.5
C8—O1—C7	106.41 (15)	H10A—C10—H10C	109.5
C8—C1—C2	107.61 (16)	H10B—C10—H10C	109.5
C8—C1—S	118.44 (15)	C6—C11—H11A	109.5
C2—C1—S	133.91 (15)	C6—C11—H11B	109.5
C7—C2—C3	118.25 (18)	H11A—C11—H11B	109.5
C7—C2—C1	104.08 (16)	C6—C11—H11C	109.5
C3—C2—C1	137.67 (18)	H11A—C11—H11C	109.5
C4—C3—C2	116.62 (18)	H11B—C11—H11C	109.5
C4—C3—C9	120.07 (19)	C8—C12—H12A	109.5
C2—C3—C9	123.30 (18)	C8—C12—H12B	109.5
C3—C4—C5	123.73 (19)	H12A—C12—H12B	109.5
C3—C4—H4	118.1	C8—C12—H12C	109.5
C5—C4—H4	118.1	H12A—C12—H12C	109.5
C6—C5—C4	120.03 (18)	H12B—C12—H12C	109.5
C6—C5—C10	121.0 (2)	C14—C13—C18	121.06 (19)
C4—C5—C10	119.0 (2)	C14—C13—S	118.92 (15)
C7—C6—C5	114.95 (18)	C18—C13—S	119.72 (16)
C7—C6—C11	120.7 (2)	C13—C14—C15	120.07 (18)
C5—C6—C11	124.32 (19)	C13—C14—H14	120.0
O1—C7—C6	122.64 (18)	C15—C14—H14	120.0
O1—C7—C2	110.96 (16)	C16—C15—C14	117.8 (2)
C6—C7—C2	126.40 (19)	C16—C15—H15	121.1
C1—C8—O1	110.94 (17)	C14—C15—H15	121.1
C1—C8—C12	133.67 (17)	F—C16—C15	118.1 (2)
O1—C8—C12	115.30 (17)	F—C16—C17	118.86 (19)
C3—C9—H9A	109.5	C15—C16—C17	123.0 (2)
C3—C9—H9B	109.5	C18—C17—C16	118.98 (19)
H9A—C9—H9B	109.5	C18—C17—H17	120.5
C3—C9—H9C	109.5	C16—C17—H17	120.5
H9A—C9—H9C	109.5	C17—C18—C13	119.01 (19)
H9B—C9—H9C	109.5	C17—C18—H18	120.5
C5—C10—H10A	109.5	C13—C18—H18	120.5

O2—S—C1—C8	137.99 (16)	C11—C6—C7—C2	−179.11 (19)
C13—S—C1—C8	−110.10 (17)	C3—C2—C7—O1	−179.38 (16)
O2—S—C1—C2	−44.4 (2)	C1—C2—C7—O1	0.3 (2)
C13—S—C1—C2	67.5 (2)	C3—C2—C7—C6	−0.1 (3)
C8—C1—C2—C7	−0.4 (2)	C1—C2—C7—C6	179.60 (18)
S—C1—C2—C7	−178.16 (16)	C2—C1—C8—O1	0.3 (2)
C8—C1—C2—C3	179.2 (2)	S—C1—C8—O1	178.51 (13)
S—C1—C2—C3	1.4 (4)	C2—C1—C8—C12	−176.0 (2)
C7—C2—C3—C4	0.3 (3)	S—C1—C8—C12	2.2 (3)
C1—C2—C3—C4	−179.3 (2)	C7—O1—C8—C1	−0.1 (2)
C7—C2—C3—C9	179.36 (18)	C7—O1—C8—C12	176.90 (17)
C1—C2—C3—C9	−0.2 (4)	O2—S—C13—C14	−13.62 (19)
C2—C3—C4—C5	0.6 (3)	C1—S—C13—C14	−128.35 (17)
C9—C3—C4—C5	−178.50 (19)	O2—S—C13—C18	172.58 (16)
C3—C4—C5—C6	−1.7 (3)	C1—S—C13—C18	57.85 (18)
C3—C4—C5—C10	177.73 (19)	C18—C13—C14—C15	−1.0 (3)
C4—C5—C6—C7	1.7 (3)	S—C13—C14—C15	−174.70 (16)
C10—C5—C6—C7	−177.71 (18)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C11	179.86 (19)	C14—C15—C16—F	−179.6 (2)
C10—C5—C6—C11	0.4 (3)	C14—C15—C16—C17	0.2 (4)
C8—O1—C7—C6	−179.43 (18)	F—C16—C17—C18	179.0 (2)
C8—O1—C7—C2	−0.12 (19)	C15—C16—C17—C18	−0.8 (4)
C5—C6—C7—O1	178.31 (17)	C16—C17—C18—C13	0.6 (4)
C11—C6—C7—O1	0.1 (3)	C14—C13—C18—C17	0.3 (3)
C5—C6—C7—C2	−0.9 (3)	S—C13—C18—C17	173.99 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.59	3.529 (3)	169
C18—H18···O2ⁱⁱ	0.95	2.49	3.328 (2)	147
C11—H11A···Cgⁱⁱ	0.98	2.66	3.553 (3)	152
C12—H12A···Cgⁱⁱⁱ	0.98	2.78	3.590 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FO₂S
M_r	316.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	169
a, b, c (Å)	12.0034 (5), 19.7455 (7), 6.4918 (3)
V (Å³)	1538.64 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.18 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.644, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8107, 2280, 2175
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.06
No. of reflections	2280
No. of parameters	204
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28
Absolute structure	Flack (1983), 366 Friedel pairs
Absolute structure parameter	0.01 (12)

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 C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.59	3.529 (3)	168.5
C18—H18···O2ⁱⁱ	0.95	2.49	3.328 (2)	147.2
C11—H11A···Cgⁱⁱ	0.98	2.66	3.553 (3)	152.4
C12—H12A···Cgⁱⁱⁱ	0.98	2.78	3.590 (3)	140.7

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

References

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Volume 66| Part 3| March 2010| Page o643

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