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

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

doi:10.1107/S1600536809055068

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o258

https://doi.org/10.1107/S1600536809055068

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5-Fluoro-2-methyl-3-phenylsulfonyl-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 30 November 2009; accepted 22 December 2009; online 9 January 2010)

There are two symmetry-independent molecules, A and B, in the asymmetric unit of the title compound, C₁₅H₁₁FO₃S. The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. In the crystal structure, the two independent molecules are related by a pseudo-inversion center. The dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 80.2 (1)° in molecule A and 80.7 (1)° in molecule B. In the crystal structure, the A and B molecules are linked by aromatic π–π interactions between the furan and benzene rings of neighbouring benzofuran systems; the centroid–centroid distances are 3.671 (7) and 3.715 (7) Å. In addition, the crystal structure also exhibits two weak non-classical intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ,b ,c ). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₁FO₃S
M_r = 290.30
Monoclinic, P 2₁
a = 7.377 (2) Å
b = 19.831 (4) Å
c = 9.025 (2) Å
β = 101.367 (3)°
V = 1294.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 173 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.930, T_max = 0.990
6055 measured reflections
3996 independent reflections
3154 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.115
S = 1.07
3996 reflections
362 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 1642 Friedel pairs
Flack parameter: 0.21 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6ⁱ	0.93	2.60	3.494 (6)	162
C26—H26⋯O2ⁱⁱ	0.93	2.55	3.479 (7)	174
Symmetry codes: (i) x, y, z-1; (ii) 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 datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055068/ng2699sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055068/ng2699Isup2.hkl

checkCIF report

Comment top

Molecules involving benzofuran skeleton have attracted considerable interest in the view of their presence in natural products (Akgul & Anil, 2003; Soekamto et al., 2003) and their biological activity (Aslam et al., 2006; Galal et al., 2009). As a part of our continuing studies of the effect of side chain substituents on the solid state structures of 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a, b, c), we report the crystal structure of the title compound (Fig. 1). The crystal studied was an inversion twin with a 0.21 (12):0.79 (12) domain ratio. It crystallized in the monoclinic space group P2₁, with two symmetry-independent molecules, A and B, in the asymmetric unit.

The benzofuran unit is essentially planar, with a mean deviation of 0.011 (4) Å for A molecule and 0.007 (4) Å for B molecule, respectively, from the least-squares plane defined by the nine constituent atoms. In the title compound, the dihedral angles formed by the phenyl ring and the plane of the benzofuran fragment are 80.2 (1)° in molecule A and 80.7 (1)° in molecule B, respectively. In the crystal packing (Fig. 2), the A and B molecules are linked by two different aromatic π–π interactions; the first between the furan ring (Cg1) and an adjacent benzene ring (Cg4) [distance = 3.671 (7) Å], the second between the furan ring (Cg3) and an adjacent benzene ring (Cg2) [distance = 3.715 (7) Å], (Cg1, Cg2, Cg3, and Cg4 are the centroids of the C1/C2/C7/O1/C8 furan ring, the C2–C7 benzene ring, the C16/C17/C22/O4/C23 furan ring, and the C17–C22 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by two non-classical intermolecular C—H···O hydrogen bonds; the first between the benzene H atom and the oxygen of the S═O unit, with a C3—H3···O6ⁱ, the second between the phenyl H atom and the oxygen of the S═O unit, with a C26—H26···O2ⁱⁱ, respectively (Table 1).

Related literature top

For the crystal structures of similar 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b,c). For natural products with benzofuran ring systems, see: Akgul & Anil (2003); Soekamto et al. (2003). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009).

Experimental top

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-fluoro-2-methyl-3-phenylsulfanyl-1-benzofuran (310 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 (chloroform) to afford the title compound as a colorless solid [yield 75%, m.p. 397–398 K; R_f = 0.55 (chloroform)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Structure description top

For the crystal structures of similar 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b,c). For natural products with benzofuran ring systems, see: Akgul & Anil (2003); Soekamto et al. (2003). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009).

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. π–π and C—H···O interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) x, y, z - 1; (ii) x, y, z + 1.]

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

Crystal data top

C₁₅H₁₁FO₃S	F(000) = 600
M_r = 290.30	D_x = 1.490 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2yb	Cell parameters from 2528 reflections
a = 7.377 (2) Å	θ = 2.3–25.7°
b = 19.831 (4) Å	µ = 0.27 mm⁻¹
c = 9.025 (2) Å	T = 173 K
β = 101.367 (3)°	Block, colourless
V = 1294.4 (5) Å³	0.40 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3996 independent reflections
Radiation source: Rotating Anode	3154 reflections with I > 2σ(I)
HELIOS monochromator	R_int = 0.062
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −19→23
T_min = 0.930, T_max = 0.990	l = −10→10
6055 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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0406P)² + 0.9464P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3996 reflections	Δρ_max = 0.26 e Å⁻³
362 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1642 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.21 (12)

Crystal data top

C₁₅H₁₁FO₃S	V = 1294.4 (5) Å³
M_r = 290.30	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 7.377 (2) Å	µ = 0.27 mm⁻¹
b = 19.831 (4) Å	T = 173 K
c = 9.025 (2) Å	0.40 × 0.20 × 0.05 mm
β = 101.367 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3996 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3154 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.990	R_int = 0.062
6055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.115	Δρ_max = 0.26 e Å⁻³
S = 1.07	Δρ_min = −0.35 e Å⁻³
3996 reflections	Absolute structure: Flack (1983), 1642 Friedel pairs
362 parameters	Absolute structure parameter: 0.21 (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
S1	0.40869 (16)	0.34079 (7)	0.07406 (13)	0.0315 (3)
S2	0.29228 (16)	0.56069 (6)	0.66799 (14)	0.0314 (3)
O1	0.6428 (5)	0.40440 (18)	0.4794 (4)	0.0356 (9)
O2	0.2917 (5)	0.38775 (19)	−0.0206 (4)	0.0366 (10)
O3	0.3351 (5)	0.27849 (19)	0.1139 (4)	0.0419 (10)
O4	0.0634 (5)	0.5048 (2)	0.2569 (4)	0.0380 (10)
O5	0.3689 (5)	0.62390 (18)	0.6366 (4)	0.0396 (9)
O6	0.4061 (5)	0.51239 (18)	0.7608 (4)	0.0370 (9)
F1	0.5315 (5)	0.62712 (18)	0.1306 (4)	0.0595 (10)
F2	0.1460 (5)	0.27594 (17)	0.5845 (4)	0.0573 (10)
C1	0.5062 (6)	0.3838 (3)	0.2392 (5)	0.0292 (12)
C2	0.5405 (6)	0.4548 (3)	0.2512 (5)	0.0277 (12)
C3	0.5098 (7)	0.5105 (3)	0.1556 (6)	0.0326 (13)
H3	0.4560	0.5063	0.0537	0.039*
C4	0.5630 (8)	0.5711 (3)	0.2194 (6)	0.0409 (14)
C5	0.6451 (8)	0.5809 (3)	0.3707 (7)	0.0438 (16)
H5	0.6773	0.6240	0.4072	0.053*
C6	0.6775 (7)	0.5265 (3)	0.4641 (7)	0.0388 (14)
H6	0.7324	0.5311	0.5656	0.047*
C7	0.6260 (7)	0.4647 (3)	0.4027 (6)	0.0323 (13)
C8	0.5701 (7)	0.3559 (3)	0.3777 (6)	0.0321 (13)
C9	0.5796 (8)	0.2868 (3)	0.4372 (6)	0.0403 (15)
H9A	0.5129	0.2842	0.5183	0.048*
H9B	0.7065	0.2747	0.4742	0.048*
H9C	0.5257	0.2563	0.3582	0.048*
C10	0.5988 (7)	0.3223 (3)	−0.0108 (6)	0.0301 (13)
C11	0.6510 (7)	0.3687 (3)	−0.1085 (6)	0.0390 (14)
H11	0.5833	0.4080	−0.1342	0.047*
C12	0.8080 (7)	0.3549 (3)	−0.1675 (6)	0.0412 (15)
H12	0.8470	0.3854	−0.2330	0.049*
C13	0.9051 (8)	0.2966 (4)	−0.1293 (7)	0.0495 (17)
H13	1.0108	0.2881	−0.1679	0.059*
C14	0.8482 (8)	0.2507 (3)	−0.0353 (7)	0.0452 (15)
H14	0.9139	0.2109	−0.0119	0.054*
C15	0.6935 (7)	0.2634 (3)	0.0255 (6)	0.0394 (14)
H15	0.6544	0.2323	0.0898	0.047*
C16	0.1980 (6)	0.5209 (3)	0.4988 (5)	0.0275 (11)
C17	0.1588 (7)	0.4501 (3)	0.4804 (6)	0.0300 (12)
C18	0.1820 (7)	0.3933 (3)	0.5702 (6)	0.0341 (14)
H18	0.2355	0.3952	0.6725	0.041*
C19	0.1217 (7)	0.3339 (3)	0.5001 (7)	0.0366 (14)
C20	0.0419 (8)	0.3273 (3)	0.3496 (7)	0.0431 (15)
H20	0.0051	0.2852	0.3094	0.052*
C21	0.0171 (7)	0.3837 (3)	0.2591 (6)	0.0409 (14)
H21	−0.0357	0.3812	0.1568	0.049*
C22	0.0738 (7)	0.4434 (3)	0.3272 (6)	0.0320 (13)
C23	0.1387 (7)	0.5516 (3)	0.3642 (6)	0.0327 (13)
C24	0.1323 (8)	0.6216 (3)	0.3081 (7)	0.0478 (16)
H24A	0.0060	0.6345	0.2711	0.057*
H24B	0.1999	0.6247	0.2278	0.057*
H24C	0.1867	0.6511	0.3890	0.057*
C25	0.0987 (7)	0.5777 (3)	0.7488 (6)	0.0293 (13)
C26	0.0476 (7)	0.5332 (3)	0.8495 (6)	0.0375 (14)
H26	0.1157	0.4941	0.8776	0.045*
C27	−0.1081 (8)	0.5478 (3)	0.9085 (7)	0.0490 (17)
H27	−0.1435	0.5187	0.9786	0.059*
C28	−0.2091 (8)	0.6040 (3)	0.8651 (7)	0.0461 (17)
H28	−0.3129	0.6131	0.9057	0.055*
C29	−0.1597 (8)	0.6481 (3)	0.7610 (7)	0.0434 (15)
H29	−0.2305	0.6863	0.7310	0.052*
C30	−0.0042 (7)	0.6347 (3)	0.7022 (6)	0.0385 (13)
H30	0.0307	0.6637	0.6319	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0254 (7)	0.0406 (8)	0.0272 (7)	−0.0029 (6)	0.0021 (5)	−0.0014 (6)
S2	0.0266 (7)	0.0380 (8)	0.0283 (7)	−0.0013 (6)	0.0019 (5)	−0.0018 (6)
O1	0.039 (2)	0.041 (3)	0.025 (2)	0.0029 (17)	0.0014 (16)	0.0001 (18)
O2	0.029 (2)	0.046 (3)	0.032 (2)	0.0034 (18)	−0.0032 (16)	−0.0049 (19)
O3	0.041 (2)	0.047 (3)	0.037 (2)	−0.0117 (18)	0.0056 (18)	0.0009 (19)
O4	0.040 (2)	0.047 (3)	0.027 (2)	0.0071 (18)	0.0053 (16)	0.0018 (19)
O5	0.035 (2)	0.039 (2)	0.045 (2)	−0.0052 (18)	0.0084 (17)	−0.0042 (19)
O6	0.030 (2)	0.046 (2)	0.033 (2)	0.0040 (17)	0.0001 (16)	0.0034 (19)
F1	0.083 (3)	0.043 (2)	0.057 (2)	0.0025 (19)	0.0235 (19)	0.0091 (18)
F2	0.083 (3)	0.043 (2)	0.047 (2)	−0.0026 (18)	0.0171 (19)	0.0020 (17)
C1	0.019 (3)	0.041 (4)	0.025 (3)	−0.002 (2)	0.001 (2)	−0.001 (2)
C2	0.020 (3)	0.043 (4)	0.020 (3)	−0.001 (2)	0.005 (2)	−0.004 (2)
C3	0.032 (3)	0.041 (4)	0.025 (3)	0.002 (2)	0.006 (2)	−0.001 (3)
C4	0.046 (3)	0.037 (4)	0.042 (3)	0.004 (3)	0.016 (3)	0.005 (3)
C5	0.041 (3)	0.046 (4)	0.047 (4)	−0.006 (3)	0.015 (3)	−0.012 (3)
C6	0.033 (3)	0.053 (4)	0.030 (3)	−0.004 (3)	0.006 (2)	−0.014 (3)
C7	0.026 (3)	0.046 (4)	0.025 (3)	0.002 (2)	0.005 (2)	−0.002 (3)
C8	0.026 (3)	0.038 (4)	0.032 (3)	0.004 (2)	0.006 (2)	−0.001 (3)
C9	0.043 (4)	0.047 (4)	0.028 (3)	−0.003 (3)	0.001 (3)	0.006 (3)
C10	0.030 (3)	0.043 (4)	0.016 (2)	−0.002 (2)	0.000 (2)	−0.004 (2)
C11	0.035 (3)	0.053 (4)	0.027 (3)	−0.004 (3)	−0.001 (2)	−0.002 (3)
C12	0.036 (3)	0.071 (5)	0.015 (3)	−0.009 (3)	0.002 (2)	−0.001 (3)
C13	0.038 (4)	0.074 (5)	0.037 (4)	0.004 (3)	0.011 (3)	−0.010 (3)
C14	0.042 (3)	0.054 (4)	0.036 (3)	0.012 (3)	−0.001 (3)	−0.010 (3)
C15	0.036 (3)	0.044 (4)	0.038 (3)	0.002 (3)	0.006 (3)	−0.011 (3)
C16	0.025 (3)	0.034 (3)	0.024 (3)	0.003 (2)	0.004 (2)	0.003 (2)
C17	0.019 (3)	0.040 (4)	0.031 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C18	0.033 (3)	0.041 (4)	0.030 (3)	−0.001 (2)	0.008 (2)	0.000 (3)
C19	0.033 (3)	0.035 (4)	0.042 (3)	0.000 (3)	0.010 (3)	0.005 (3)
C20	0.038 (3)	0.050 (4)	0.040 (3)	−0.009 (3)	0.006 (3)	−0.012 (3)
C21	0.039 (3)	0.057 (4)	0.026 (3)	0.000 (3)	0.005 (2)	−0.011 (3)
C22	0.027 (3)	0.045 (4)	0.024 (3)	0.002 (2)	0.005 (2)	−0.001 (3)
C23	0.030 (3)	0.039 (4)	0.031 (3)	0.001 (2)	0.012 (2)	0.000 (3)
C24	0.054 (4)	0.051 (4)	0.040 (4)	0.015 (3)	0.013 (3)	0.007 (3)
C25	0.023 (3)	0.039 (4)	0.024 (3)	−0.002 (2)	0.001 (2)	−0.007 (3)
C26	0.027 (3)	0.054 (4)	0.029 (3)	−0.003 (2)	−0.001 (2)	0.003 (3)
C27	0.036 (3)	0.081 (5)	0.031 (3)	−0.004 (3)	0.008 (3)	0.004 (3)
C28	0.031 (3)	0.077 (5)	0.029 (3)	−0.004 (3)	0.002 (3)	−0.023 (3)
C29	0.035 (3)	0.043 (4)	0.050 (4)	0.009 (3)	0.003 (3)	−0.011 (3)
C30	0.043 (3)	0.034 (3)	0.041 (3)	0.000 (3)	0.013 (3)	−0.001 (3)

Geometric parameters (Å, º) top

S1—O3	1.424 (4)	C12—C13	1.368 (8)
S1—O2	1.432 (4)	C12—H12	0.9300
S1—C1	1.744 (5)	C13—C14	1.365 (8)
S1—C10	1.764 (6)	C13—H13	0.9300
S2—O5	1.426 (4)	C14—C15	1.383 (8)
S2—O6	1.430 (4)	C14—H14	0.9300
S2—C16	1.738 (5)	C15—H15	0.9300
S2—C25	1.759 (5)	C16—C23	1.352 (7)
O1—C8	1.364 (6)	C16—C17	1.437 (7)
O1—C7	1.375 (6)	C17—C18	1.378 (7)
O4—C22	1.369 (6)	C17—C22	1.408 (7)
O4—C23	1.377 (6)	C18—C19	1.369 (8)
F1—C4	1.363 (6)	C18—H18	0.9300
F2—C19	1.371 (7)	C19—C20	1.377 (8)
C1—C8	1.364 (7)	C20—C21	1.375 (8)
C1—C2	1.431 (7)	C20—H20	0.9300
C2—C3	1.392 (7)	C21—C22	1.361 (8)
C2—C7	1.402 (7)	C21—H21	0.9300
C3—C4	1.357 (8)	C23—C24	1.474 (7)
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.393 (8)	C24—H24B	0.9600
C5—C6	1.361 (8)	C24—H24C	0.9600
C5—H5	0.9300	C25—C26	1.372 (7)
C6—C7	1.368 (8)	C25—C30	1.381 (7)
C6—H6	0.9300	C26—C27	1.389 (8)
C8—C9	1.469 (8)	C26—H26	0.9300
C9—H9A	0.9600	C27—C28	1.356 (8)
C9—H9B	0.9600	C27—H27	0.9300
C9—H9C	0.9600	C28—C29	1.383 (8)
C10—C15	1.368 (7)	C28—H28	0.9300
C10—C11	1.380 (8)	C29—C30	1.381 (8)
C11—C12	1.394 (8)	C29—H29	0.9300
C11—H11	0.9300	C30—H30	0.9300

O3—S1—O2	120.0 (2)	C12—C13—H13	119.7
O3—S1—C1	108.8 (2)	C13—C14—C15	120.3 (6)
O2—S1—C1	106.9 (2)	C13—C14—H14	119.8
O3—S1—C10	107.7 (2)	C15—C14—H14	119.8
O2—S1—C10	108.3 (2)	C10—C15—C14	118.8 (6)
C1—S1—C10	104.1 (2)	C10—C15—H15	120.6
O5—S2—O6	119.7 (2)	C14—C15—H15	120.6
O5—S2—C16	109.3 (2)	C23—C16—C17	108.3 (4)
O6—S2—C16	107.3 (2)	C23—C16—S2	126.0 (4)
O5—S2—C25	107.5 (2)	C17—C16—S2	125.6 (4)
O6—S2—C25	108.4 (2)	C18—C17—C22	118.7 (5)
C16—S2—C25	103.5 (2)	C18—C17—C16	137.1 (5)
C8—O1—C7	106.9 (4)	C22—C17—C16	104.3 (4)
C22—O4—C23	107.2 (4)	C19—C18—C17	116.1 (5)
C8—C1—C2	107.8 (4)	C19—C18—H18	122.0
C8—C1—S1	126.5 (4)	C17—C18—H18	122.0
C2—C1—S1	125.7 (4)	C18—C19—F2	118.0 (5)
C3—C2—C7	118.7 (5)	C18—C19—C20	125.1 (6)
C3—C2—C1	136.7 (5)	F2—C19—C20	116.9 (5)
C7—C2—C1	104.5 (4)	C21—C20—C19	119.3 (6)
C4—C3—C2	116.2 (5)	C21—C20—H20	120.3
C4—C3—H3	121.9	C19—C20—H20	120.3
C2—C3—H3	121.9	C22—C21—C20	116.4 (5)
C3—C4—F1	118.1 (5)	C22—C21—H21	121.8
C3—C4—C5	125.0 (6)	C20—C21—H21	121.8
F1—C4—C5	116.9 (6)	C21—C22—O4	125.5 (5)
C6—C5—C4	119.1 (6)	C21—C22—C17	124.4 (5)
C6—C5—H5	120.5	O4—C22—C17	110.1 (5)
C4—C5—H5	120.5	C16—C23—O4	110.0 (4)
C5—C6—C7	117.2 (5)	C16—C23—C24	135.6 (5)
C5—C6—H6	121.4	O4—C23—C24	114.3 (5)
C7—C6—H6	121.4	C23—C24—H24A	109.5
C6—C7—O1	125.8 (5)	C23—C24—H24B	109.5
C6—C7—C2	123.8 (5)	H24A—C24—H24B	109.5
O1—C7—C2	110.4 (5)	C23—C24—H24C	109.5
C1—C8—O1	110.5 (5)	H24A—C24—H24C	109.5
C1—C8—C9	134.2 (5)	H24B—C24—H24C	109.5
O1—C8—C9	115.3 (4)	C26—C25—C30	121.5 (5)
C8—C9—H9A	109.5	C26—C25—S2	120.2 (4)
C8—C9—H9B	109.5	C30—C25—S2	118.2 (4)
H9A—C9—H9B	109.5	C25—C26—C27	118.4 (5)
C8—C9—H9C	109.5	C25—C26—H26	120.8
H9A—C9—H9C	109.5	C27—C26—H26	120.8
H9B—C9—H9C	109.5	C28—C27—C26	120.6 (6)
C15—C10—C11	121.9 (5)	C28—C27—H27	119.7
C15—C10—S1	119.1 (4)	C26—C27—H27	119.7
C11—C10—S1	119.0 (4)	C27—C28—C29	120.9 (6)
C10—C11—C12	118.1 (6)	C27—C28—H28	119.6
C10—C11—H11	120.9	C29—C28—H28	119.6
C12—C11—H11	120.9	C30—C29—C28	119.3 (6)
C13—C12—C11	120.1 (6)	C30—C29—H29	120.4
C13—C12—H12	119.9	C28—C29—H29	120.4
C11—C12—H12	119.9	C25—C30—C29	119.3 (5)
C14—C13—C12	120.7 (6)	C25—C30—H30	120.4
C14—C13—H13	119.7	C29—C30—H30	120.4

O3—S1—C1—C8	24.1 (5)	O5—S2—C16—C23	−24.0 (5)
O2—S1—C1—C8	155.0 (4)	O6—S2—C16—C23	−155.2 (4)
C10—S1—C1—C8	−90.6 (5)	C25—S2—C16—C23	90.3 (5)
O3—S1—C1—C2	−158.9 (4)	O5—S2—C16—C17	160.2 (4)
O2—S1—C1—C2	−28.0 (5)	O6—S2—C16—C17	29.1 (5)
C10—S1—C1—C2	86.5 (5)	C25—S2—C16—C17	−85.5 (4)
C8—C1—C2—C3	−179.6 (6)	C23—C16—C17—C18	−179.4 (6)
S1—C1—C2—C3	2.8 (8)	S2—C16—C17—C18	−3.0 (8)
C8—C1—C2—C7	−0.1 (5)	C23—C16—C17—C22	−0.1 (5)
S1—C1—C2—C7	−177.6 (4)	S2—C16—C17—C22	176.3 (4)
C7—C2—C3—C4	−1.4 (7)	C22—C17—C18—C19	1.1 (7)
C1—C2—C3—C4	178.1 (5)	C16—C17—C18—C19	−179.7 (5)
C2—C3—C4—F1	−178.5 (4)	C17—C18—C19—F2	178.5 (4)
C2—C3—C4—C5	0.3 (8)	C17—C18—C19—C20	0.2 (8)
C3—C4—C5—C6	0.5 (9)	C18—C19—C20—C21	−0.5 (9)
F1—C4—C5—C6	179.3 (5)	F2—C19—C20—C21	−178.9 (5)
C4—C5—C6—C7	−0.2 (8)	C19—C20—C21—C22	−0.4 (8)
C5—C6—C7—O1	−178.2 (5)	C20—C21—C22—O4	179.2 (5)
C5—C6—C7—C2	−0.9 (8)	C20—C21—C22—C17	1.7 (8)
C8—O1—C7—C6	178.1 (5)	C23—O4—C22—C21	−178.6 (5)
C8—O1—C7—C2	0.5 (5)	C23—O4—C22—C17	−0.9 (5)
C3—C2—C7—C6	1.8 (7)	C18—C17—C22—C21	−2.1 (8)
C1—C2—C7—C6	−177.9 (5)	C16—C17—C22—C21	178.4 (5)
C3—C2—C7—O1	179.4 (4)	C18—C17—C22—O4	−179.9 (4)
C1—C2—C7—O1	−0.3 (5)	C16—C17—C22—O4	0.6 (5)
C2—C1—C8—O1	0.4 (5)	C17—C16—C23—O4	−0.5 (5)
S1—C1—C8—O1	177.9 (3)	S2—C16—C23—O4	−176.8 (3)
C2—C1—C8—C9	−178.3 (5)	C17—C16—C23—C24	177.9 (5)
S1—C1—C8—C9	−0.8 (8)	S2—C16—C23—C24	1.5 (9)
C7—O1—C8—C1	−0.6 (5)	C22—O4—C23—C16	0.9 (5)
C7—O1—C8—C9	178.4 (4)	C22—O4—C23—C24	−177.9 (4)
O3—S1—C10—C15	−26.1 (5)	O5—S2—C25—C26	−150.5 (4)
O2—S1—C10—C15	−157.2 (4)	O6—S2—C25—C26	−19.8 (5)
C1—S1—C10—C15	89.3 (5)	C16—S2—C25—C26	93.9 (4)
O3—S1—C10—C11	155.8 (4)	O5—S2—C25—C30	32.8 (5)
O2—S1—C10—C11	24.6 (5)	O6—S2—C25—C30	163.5 (4)
C1—S1—C10—C11	−88.8 (4)	C16—S2—C25—C30	−82.8 (5)
C15—C10—C11—C12	−1.8 (8)	C30—C25—C26—C27	−2.2 (8)
S1—C10—C11—C12	176.3 (4)	S2—C25—C26—C27	−178.8 (4)
C10—C11—C12—C13	0.5 (8)	C25—C26—C27—C28	1.3 (8)
C11—C12—C13—C14	1.0 (9)	C26—C27—C28—C29	0.1 (9)
C12—C13—C14—C15	−1.4 (9)	C27—C28—C29—C30	−0.7 (9)
C11—C10—C15—C14	1.4 (8)	C26—C25—C30—C29	1.6 (8)
S1—C10—C15—C14	−176.7 (4)	S2—C25—C30—C29	178.3 (4)
C13—C14—C15—C10	0.2 (8)	C28—C29—C30—C25	−0.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.93	2.60	3.494 (6)	162
C26—H26···O2ⁱⁱ	0.93	2.55	3.479 (7)	174

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁FO₃S
M_r	290.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.377 (2), 19.831 (4), 9.025 (2)
β (°)	101.367 (3)
V (Å³)	1294.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.930, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	6055, 3996, 3154
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.115, 1.07
No. of reflections	3996
No. of parameters	362
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.35
Absolute structure	Flack (1983), 1642 Friedel pairs
Absolute structure parameter	0.21 (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

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.93	2.60	3.494 (6)	161.5
C26—H26···O2ⁱⁱ	0.93	2.55	3.479 (7)	174.4

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

References

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