2-(4-Fluoro­phen­yl)-3-methyl­sulfinyl-5-phenyl-1-benzofuran

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

doi:10.1107/S1600536810014613

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1167

https://doi.org/10.1107/S1600536810014613

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2-(4-Fluorophenyl)-3-methylsulfinyl-5-phenyl-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 23 February 2010; accepted 20 April 2010; online 24 April 2010)

In the title molecule, C₂₁H₁₅FO₂S, the O atom and the methyl group of the methylsulfinyl substituent are situated on the opposite sides of the plane through the benzofuran fragment. The benzofuran ring plane makes dihedral angles of 28.63 (6) and 31.55 (5)° with the 4-fluorophenyl and phenyl rings, respectively. Weak C—H⋯F and C—H⋯O hydrogen bonds and intermolecular C—H⋯π interactions are present in the crystal structure. The title crystal was refined as an inversion twin with a 0.39 (7):0.61 (7) domain ratio.

Related literature

For the crystal structures of similar 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009 , 2010 ). For the pharmacological 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 ). For hydrogen bonding, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

C₂₁H₁₅FO₂S
M_r = 350.39
Monoclinic, P 2₁
a = 10.148 (2) Å
b = 7.117 (1) Å
c = 11.991 (2) Å
β = 110.047 (2)°
V = 813.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.917, T_max = 0.947
4812 measured reflections
3226 independent reflections
3065 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.06
3226 reflections
228 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1308 Friedel pairs
Flack parameter: 0.39 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C15–C20 (5-phenyl) and the C9–14 (4-fluorophenyl) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.61	3.301 (3)	131
C21—H21A⋯O2ⁱⁱ	0.96	2.63	3.375 (3)	135
C21—H21B⋯Fⁱⁱⁱ	0.96	2.55	3.478 (3)	164
C10—H10⋯Cg1^iv	0.93	2.86	3.450 (2)	122
C13—H13⋯Cg2ⁱⁱⁱ	0.93	2.81	3.417 (2)	124
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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: https://doi.org/10.1107/S1600536810014613/fb2185sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014613/fb2185Isup2.hkl

checkCIF report

Comment top

The compounds with the benzofuran skeleton show significant pharmacological activities such as fungicide (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009) and antimicrobial (Khan et al., 2005) properties. These compounds are common in Nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of the side chain substituents on the solid state structures of 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran analogues (Choi et al., 2009, 2010), we report the title crystal structure. The title molecule is depicted in Fig. 1.

The benzofuran ring is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. In the molecule, the benzofuran plane makes dihedral angles of 28.63 (6) and 31.55 (5)° with the 4-fluorophenyl ring and the phenyl ring, respectively. The molecular packing (Fig. 2) is stabilized by an intermolecular C—H···F hydrogen bond between the methyl H atom and the fluorine (Tab. 1). There are also C—H···O interactions (Tab. 1 and Fig. 2) with geometrical parameters that are on the limit of their acceptance as true weak C—H···O hydrogen bonds (Desiraju & Steiner, 1999). The molecular packing (Fig. 3) is further stabilized by two intermolecular C—H···π-electron ring interactions: The first one between the 4-fluorophenyl H atom and the 5-phenyl ring, and the second one between the 4-fluorophenyl H atom and 4-fluorophenyl ring (Tab. 1).

Related literature top

For the crystal structures of similar 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009, 2010). For the pharmacological 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). For hydrogen bonding, see: Desiraju & Steiner (1999).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran (301 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After having been stirred at room temperature for 4h, the mixture was washed with saturated sodium hydrogencarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (silica gel, hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colourless solid [yield 80%, m.p. 506–507 K; R_f = 0.59 (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 chloroform at room temperature. The average crystal size was approximately 1.0 × 1.0 × 0.5 mm. (The measured crystal was cut from the larger one.) The crystals are colourless and soluble in polar solvents.

Structure description top

For the crystal structures of similar 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009, 2010). For the pharmacological 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). For hydrogen bonding, see: Desiraju & Steiner (1999).

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 title molecule with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are depicted as small spheres of arbitrary radius.
	Fig. 2. C—H···F and C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x, y-1/2, -z+1; (ii) -x+1, y-1/2, -z+2; (iii) -x+2, y-1/2, -z+2; (v) -x, y+1/2, -z+1; (vi) -x+1, y+1/2, -z+2; (vii) -x+2, y+1/2, -z+2.]
	Fig. 3. C—H···π-electron ring interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroids. [Symmetry codes: (iii) -x+2, y-1/2, -z+2; (iv) -x+1, y+1/2, -z+1; (viii) -x+1, y-1/2, -z+1; (ix) -x+2, y+1/2, -z+2.]

2-(4-Fluorophenyl)-3-methylsulfinyl-5-phenyl-1-benzofuran top

Crystal data top

C₂₁H₁₅FO₂S	F(000) = 364
M_r = 350.39	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁	Melting point = 506–507 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.148 (2) Å	Cell parameters from 3710 reflections
b = 7.117 (1) Å	θ = 2.3–28.3°
c = 11.991 (2) Å	µ = 0.22 mm⁻¹
β = 110.047 (2)°	T = 173 K
V = 813.6 (2) Å³	Block, colourless
Z = 2	0.40 × 0.40 × 0.25 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3226 independent reflections
Radiation source: rotating anode	3065 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.019
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.8°
φ and ω scans	h = −8→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→8
T_min = 0.917, T_max = 0.947	l = −15→14
4812 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) = 0.086	w = 1/[σ²(F_o²) + (0.0516P)² + 0.1094P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3226 reflections	Δρ_max = 0.31 e Å⁻³
228 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1308 Friedel pairs
59 constraints	Absolute structure parameter: 0.39 (7)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₁H₁₅FO₂S	V = 813.6 (2) Å³
M_r = 350.39	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.148 (2) Å	µ = 0.22 mm⁻¹
b = 7.117 (1) Å	T = 173 K
c = 11.991 (2) Å	0.40 × 0.40 × 0.25 mm
β = 110.047 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3226 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3065 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.947	R_int = 0.019
4812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.086	Δρ_max = 0.31 e Å⁻³
S = 1.06	Δρ_min = −0.21 e Å⁻³
3226 reflections	Absolute structure: Flack (1983), 1308 Friedel pairs
228 parameters	Absolute structure parameter: 0.39 (7)
1 restraint

Special details top

Experimental. The measured sample has been cut from the larger crystal. The crystals, both the grown ones as well as the cut one, have not been examined under the polarization microscope.

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. The diffractions 1 0 0 and 0 0 1 as well as their equivalents have been excluded from the refinement because their respective intensities significantly differed from the calculated ones.

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

	x	y	z	U_iso*/U_eq
S	0.55747 (5)	0.51643 (8)	0.86742 (4)	0.03009 (13)
F	1.26845 (12)	0.4440 (2)	1.03910 (11)	0.0425 (3)
O1	0.70363 (13)	0.4548 (2)	0.60162 (10)	0.0280 (3)
O2	0.44274 (15)	0.6590 (2)	0.83904 (13)	0.0398 (4)
C1	0.59124 (17)	0.4753 (3)	0.73449 (15)	0.0251 (4)
C2	0.48587 (19)	0.4671 (3)	0.61728 (15)	0.0257 (4)
C3	0.33954 (18)	0.4703 (3)	0.57251 (15)	0.0256 (4)
H3	0.2883	0.4810	0.6234	0.031*
C4	0.27128 (18)	0.4572 (3)	0.44981 (15)	0.0255 (4)
C5	0.35234 (19)	0.4441 (3)	0.37470 (16)	0.0286 (4)
H5	0.3061	0.4352	0.2932	0.034*
C6	0.4975 (2)	0.4439 (3)	0.41758 (16)	0.0317 (4)
H6	0.5495	0.4366	0.3672	0.038*
C7	0.56102 (19)	0.4553 (3)	0.53979 (16)	0.0264 (4)
C8	0.71883 (19)	0.4670 (3)	0.72036 (15)	0.0255 (4)
C9	0.86341 (18)	0.4633 (3)	0.80353 (15)	0.0242 (4)
C10	0.97478 (18)	0.5278 (3)	0.76948 (16)	0.0278 (4)
H10	0.9566	0.5745	0.6932	0.033*
C11	1.11179 (18)	0.5224 (3)	0.84845 (17)	0.0317 (4)
H11	1.1857	0.5663	0.8265	0.038*
C12	1.13528 (19)	0.4503 (3)	0.96030 (17)	0.0291 (4)
C13	1.0289 (2)	0.3813 (3)	0.99652 (17)	0.0288 (4)
H13	1.0484	0.3314	1.0722	0.035*
C14	0.89299 (19)	0.3886 (3)	0.91741 (16)	0.0268 (4)
H14	0.8201	0.3432	0.9402	0.032*
C15	0.11547 (19)	0.4540 (3)	0.39950 (15)	0.0250 (4)
C16	0.0356 (2)	0.3732 (3)	0.46221 (16)	0.0281 (4)
H16	0.0806	0.3231	0.5373	0.034*
C17	−0.1097 (2)	0.3669 (3)	0.41369 (17)	0.0313 (4)
H17	−0.1610	0.3139	0.4568	0.038*
C18	−0.1788 (2)	0.4392 (3)	0.30148 (18)	0.0323 (4)
H18	−0.2760	0.4326	0.2686	0.039*
C19	−0.10197 (19)	0.5216 (3)	0.23840 (16)	0.0315 (4)
H19	−0.1478	0.5718	0.1635	0.038*
C20	0.04378 (18)	0.5288 (3)	0.28756 (15)	0.0277 (4)
H20	0.0944	0.5848	0.2448	0.033*
C21	0.4775 (2)	0.2943 (4)	0.8756 (2)	0.0421 (6)
H21A	0.4490	0.2925	0.9441	0.063*
H21B	0.5438	0.1952	0.8817	0.063*
H21C	0.3970	0.2765	0.8053	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0302 (2)	0.0398 (3)	0.02136 (19)	0.0062 (2)	0.01031 (15)	−0.0019 (2)
F	0.0287 (6)	0.0505 (8)	0.0447 (7)	−0.0009 (6)	0.0080 (5)	0.0011 (6)
O1	0.0297 (7)	0.0328 (7)	0.0243 (6)	0.0016 (6)	0.0128 (5)	0.0010 (6)
O2	0.0390 (8)	0.0470 (10)	0.0350 (8)	0.0117 (7)	0.0148 (7)	−0.0033 (7)
C1	0.0285 (9)	0.0257 (11)	0.0232 (8)	0.0025 (7)	0.0116 (7)	−0.0012 (7)
C2	0.0336 (9)	0.0226 (10)	0.0228 (8)	0.0019 (7)	0.0120 (7)	0.0007 (7)
C3	0.0306 (9)	0.0244 (11)	0.0253 (8)	0.0003 (7)	0.0142 (7)	−0.0004 (7)
C4	0.0306 (9)	0.0213 (9)	0.0250 (8)	−0.0008 (8)	0.0100 (7)	0.0015 (8)
C5	0.0361 (10)	0.0289 (10)	0.0224 (8)	−0.0012 (8)	0.0122 (7)	−0.0009 (8)
C6	0.0364 (10)	0.0369 (11)	0.0269 (9)	0.0023 (9)	0.0173 (8)	0.0011 (9)
C7	0.0292 (9)	0.0247 (9)	0.0285 (9)	0.0011 (8)	0.0140 (7)	0.0003 (8)
C8	0.0322 (9)	0.0220 (10)	0.0253 (8)	0.0005 (7)	0.0135 (7)	0.0017 (7)
C9	0.0264 (9)	0.0198 (9)	0.0289 (8)	0.0020 (7)	0.0129 (7)	−0.0005 (8)
C10	0.0346 (9)	0.0241 (9)	0.0304 (8)	0.0022 (9)	0.0184 (7)	0.0027 (9)
C11	0.0311 (9)	0.0265 (10)	0.0439 (10)	−0.0006 (9)	0.0211 (8)	−0.0002 (10)
C12	0.0249 (9)	0.0264 (10)	0.0354 (9)	0.0025 (8)	0.0094 (7)	−0.0021 (9)
C13	0.0337 (11)	0.0249 (10)	0.0289 (9)	0.0027 (8)	0.0121 (8)	0.0015 (8)
C14	0.0292 (10)	0.0242 (10)	0.0310 (9)	0.0007 (7)	0.0154 (8)	0.0016 (8)
C15	0.0330 (9)	0.0196 (9)	0.0237 (8)	−0.0035 (8)	0.0114 (7)	−0.0042 (8)
C16	0.0374 (11)	0.0254 (10)	0.0234 (8)	−0.0021 (8)	0.0126 (8)	−0.0002 (8)
C17	0.0352 (10)	0.0285 (11)	0.0351 (10)	−0.0046 (8)	0.0183 (8)	−0.0027 (9)
C18	0.0265 (9)	0.0319 (11)	0.0385 (10)	−0.0017 (8)	0.0108 (8)	−0.0040 (9)
C19	0.0358 (9)	0.0270 (10)	0.0288 (8)	0.0016 (9)	0.0073 (7)	0.0011 (9)
C20	0.0342 (9)	0.0234 (9)	0.0273 (8)	−0.0040 (9)	0.0130 (7)	0.0017 (9)
C21	0.0451 (13)	0.0481 (15)	0.0405 (12)	0.0055 (11)	0.0242 (10)	0.0131 (11)

Geometric parameters (Å, º) top

S—O2	1.4931 (16)	C10—H10	0.9300
S—C1	1.7660 (17)	C11—C12	1.379 (3)
S—C21	1.795 (2)	C11—H11	0.9300
F—C12	1.359 (2)	C12—C13	1.385 (3)
O1—C8	1.381 (2)	C13—C14	1.381 (3)
O1—C7	1.382 (2)	C13—H13	0.9300
C1—C8	1.364 (2)	C14—H14	0.9300
C1—C2	1.446 (2)	C15—C20	1.395 (3)
C2—C7	1.392 (2)	C15—C16	1.404 (3)
C2—C3	1.395 (2)	C16—C17	1.388 (3)
C3—C4	1.398 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.386 (3)
C4—C5	1.416 (2)	C17—H17	0.9300
C4—C15	1.487 (2)	C18—C19	1.388 (3)
C5—C6	1.383 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.393 (2)
C6—C7	1.386 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C8—C9	1.464 (2)	C21—H21A	0.9600
C9—C14	1.399 (2)	C21—H21B	0.9600
C9—C10	1.404 (2)	C21—H21C	0.9600
C10—C11	1.389 (2)

O2—S—C1	106.52 (9)	C12—C11—H11	120.9
O2—S—C21	106.22 (10)	C10—C11—H11	120.9
C1—S—C21	97.72 (10)	F—C12—C11	119.20 (16)
C8—O1—C7	106.22 (13)	F—C12—C13	117.85 (18)
C8—C1—C2	107.14 (15)	C11—C12—C13	122.95 (18)
C8—C1—S	127.27 (14)	C14—C13—C12	118.27 (18)
C2—C1—S	125.19 (13)	C14—C13—H13	120.9
C7—C2—C3	119.90 (16)	C12—C13—H13	120.9
C7—C2—C1	105.03 (15)	C13—C14—C9	120.97 (17)
C3—C2—C1	135.07 (16)	C13—C14—H14	119.5
C2—C3—C4	118.80 (15)	C9—C14—H14	119.5
C2—C3—H3	120.6	C20—C15—C16	117.73 (17)
C4—C3—H3	120.6	C20—C15—C4	121.06 (15)
C3—C4—C5	119.18 (16)	C16—C15—C4	121.20 (16)
C3—C4—C15	120.16 (15)	C17—C16—C15	120.94 (18)
C5—C4—C15	120.66 (16)	C17—C16—H16	119.5
C6—C5—C4	122.70 (17)	C15—C16—H16	119.5
C6—C5—H5	118.7	C18—C17—C16	120.43 (18)
C4—C5—H5	118.7	C18—C17—H17	119.8
C5—C6—C7	116.31 (16)	C16—C17—H17	119.8
C5—C6—H6	121.8	C17—C18—C19	119.61 (18)
C7—C6—H6	121.8	C17—C18—H18	120.2
O1—C7—C6	126.11 (16)	C19—C18—H18	120.2
O1—C7—C2	110.78 (15)	C18—C19—C20	119.88 (17)
C6—C7—C2	123.10 (17)	C18—C19—H19	120.1
C1—C8—O1	110.83 (15)	C20—C19—H19	120.1
C1—C8—C9	133.51 (16)	C19—C20—C15	121.40 (17)
O1—C8—C9	115.64 (14)	C19—C20—H20	119.3
C14—C9—C10	118.91 (16)	C15—C20—H20	119.3
C14—C9—C8	120.10 (15)	S—C21—H21A	109.5
C10—C9—C8	120.96 (16)	S—C21—H21B	109.5
C11—C10—C9	120.69 (17)	H21A—C21—H21B	109.5
C11—C10—H10	119.7	S—C21—H21C	109.5
C9—C10—H10	119.7	H21A—C21—H21C	109.5
C12—C11—C10	118.19 (16)	H21B—C21—H21C	109.5

O2—S—C1—C8	133.81 (19)	C7—O1—C8—C9	178.29 (16)
C21—S—C1—C8	−116.67 (19)	C1—C8—C9—C14	27.8 (3)
O2—S—C1—C2	−38.02 (19)	O1—C8—C9—C14	−150.11 (18)
C21—S—C1—C2	71.50 (18)	C1—C8—C9—C10	−154.5 (2)
C8—C1—C2—C7	−0.3 (2)	O1—C8—C9—C10	27.6 (3)
S—C1—C2—C7	172.91 (16)	C14—C9—C10—C11	−1.7 (3)
C8—C1—C2—C3	−179.7 (2)	C8—C9—C10—C11	−179.48 (19)
S—C1—C2—C3	−6.5 (3)	C9—C10—C11—C12	0.7 (3)
C7—C2—C3—C4	1.4 (3)	C10—C11—C12—F	−179.86 (19)
C1—C2—C3—C4	−179.3 (2)	C10—C11—C12—C13	0.8 (3)
C2—C3—C4—C5	−1.0 (3)	F—C12—C13—C14	179.42 (18)
C2—C3—C4—C15	178.04 (17)	C11—C12—C13—C14	−1.2 (3)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—C9	0.1 (3)
C15—C4—C5—C6	−179.11 (19)	C10—C9—C14—C13	1.3 (3)
C4—C5—C6—C7	0.7 (3)	C8—C9—C14—C13	179.05 (18)
C8—O1—C7—C6	−179.6 (2)	C3—C4—C15—C20	149.0 (2)
C8—O1—C7—C2	−0.1 (2)	C5—C4—C15—C20	−32.0 (3)
C5—C6—C7—O1	179.1 (2)	C3—C4—C15—C16	−31.9 (3)
C5—C6—C7—C2	−0.3 (3)	C5—C4—C15—C16	147.1 (2)
C3—C2—C7—O1	179.75 (16)	C20—C15—C16—C17	0.5 (3)
C1—C2—C7—O1	0.3 (2)	C4—C15—C16—C17	−178.57 (19)
C3—C2—C7—C6	−0.8 (3)	C15—C16—C17—C18	0.6 (3)
C1—C2—C7—C6	179.71 (19)	C16—C17—C18—C19	−1.3 (3)
C2—C1—C8—O1	0.2 (2)	C17—C18—C19—C20	0.8 (3)
S—C1—C8—O1	−172.79 (14)	C18—C19—C20—C15	0.3 (3)
C2—C1—C8—C9	−177.7 (2)	C16—C15—C20—C19	−1.0 (3)
S—C1—C8—C9	9.2 (3)	C4—C15—C20—C19	178.14 (19)
C7—O1—C8—C1	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C15–C20 (5-phenyl) and the C9–14 (4-fluorophenyl) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.61	3.301 (3)	131
C21—H21A···O2ⁱⁱ	0.96	2.63	3.375 (3)	135
C21—H21B···Fⁱⁱⁱ	0.96	2.55	3.478 (3)	164
C10—H10···Cg1^iv	0.93	2.86	3.450 (2)	122
C13—H13···Cg2ⁱⁱⁱ	0.93	2.81	3.417 (2)	124

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FO₂S
M_r	350.39
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	10.148 (2), 7.117 (1), 11.991 (2)
β (°)	110.047 (2)
V (Å³)	813.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.40 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.917, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	4812, 3226, 3065
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.06
No. of reflections	3226
No. of parameters	228
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.21
Absolute structure	Flack (1983), 1308 Friedel pairs
Absolute structure parameter	0.39 (7)

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

Cg1 and Cg2 are the centroids of the C15–C20 (5-phenyl) and the C9–14 (4-fluorophenyl) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.61	3.301 (3)	131.4
C21—H21A···O2ⁱⁱ	0.96	2.63	3.375 (3)	134.8
C21—H21B···Fⁱⁱⁱ	0.96	2.55	3.478 (3)	163.6
C10—H10···Cg1^iv	0.93	2.86	3.450 (2)	122
C13—H13···Cg2ⁱⁱⁱ	0.93	2.81	3.417 (2)	124

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

References

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