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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2172
https://doi.org/10.1107/S1600536810029958

2-(4-Bromo­phen­yl)-5-fluoro-3-phenyl­sulfinyl-1-benzo­furan

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

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 14 July 2010; accepted 28 July 2010; online 31 July 2010)

In the title compound, C20H12BrFO2S, the O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment; the phenyl ring is nearly perpendicular to this plane [dihedral angle = 86.98 (6)°]. The 4-bromo­phenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 1.56 (8)°. The crystal structure features aromatic π–π inter­actions between the furan and phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.506 (3) Å], and an inter­molecular C—H⋯π inter­action. The crystal structure also exhibits a short inter­molecular S⋯S contact [3.2635 (8) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834]). For the structures of related 5-halo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o1809.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1958.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009c). Acta Cryst. E65, o2609.]). For short S⋯S inter­actions, see: Munshi & Guru Row (2004[Munshi, P. & Guru Row, T. N. (2004). Acta Cryst. E60, o2168-o2170.]).

[Scheme 1]

Experimental

Crystal data

  • C20H12BrFO2S

  • Mr = 415.27

  • Triclinic, [P \overline 1]

  • a = 8.1361 (4) Å

  • b = 9.8237 (5) Å

  • c = 11.4093 (5) Å

  • α = 82.866 (3)°

  • β = 77.123 (3)°

  • γ = 69.155 (2)°

  • V = 829.78 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.62 mm−1

  • T = 173 K

  • 0.29 × 0.26 × 0.21 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.664, Tmax = 0.746

  • 14582 measured reflections

  • 3833 independent reflections

  • 3452 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.104

  • S = 0.87

  • 3833 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 phenyl ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C5—H5⋯Cg3i 0.93 2.85 3.644 (3) 145
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810029958/pk2256sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029958/pk2256Isup2.hkl

checkCIF report


Comment top

Many compounds containing a benzofuran moiety have attracted considerable interest in view of their pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.063 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the phenyl ring is 86.98 (6)°, and the 4-bromophenyl ring with 1.56 (8)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the furan and benzene rings of the adjacent molecules, with a Cg1···Cg2ii distance of 3.506 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the benzene H atom and the phenyl ring of a neighbouring molecule, with a C5—H5···Cg3i (Table 1; Cg3 is the centroid of the C15–C20 phenyl ring). The crystal structure also exhibits a short intermolecular S···S contact (Munshi & Guru Row, 2004), with a S···Siv distance of 3.2635 (8) Å

Related literature top

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 the structures of related 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b,c). For short S···S interactions, see: Munshi & Guru Row (2004).

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-bromophenyl)-5-fluoro-3-phenylsulfanyl-1-benzofuran (439 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 68%, m.p. 465–466 K; Rf = 0.75 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

Many compounds containing a benzofuran moiety have attracted considerable interest in view of their pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.063 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the phenyl ring is 86.98 (6)°, and the 4-bromophenyl ring with 1.56 (8)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the furan and benzene rings of the adjacent molecules, with a Cg1···Cg2ii distance of 3.506 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by an intermolecular C—H···π interaction between the benzene H atom and the phenyl ring of a neighbouring molecule, with a C5—H5···Cg3i (Table 1; Cg3 is the centroid of the C15–C20 phenyl ring). The crystal structure also exhibits a short intermolecular S···S contact (Munshi & Guru Row, 2004), with a S···Siv distance of 3.2635 (8) Å

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 the structures of related 5-halo-2-phenyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b,c). For short S···S interactions, see: Munshi & Guru Row (2004).

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
[Figure 1] 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.
[Figure 2] Fig. 2. π–π, C—H···π and S···S interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroids. [Symmetry codes: (i) x, y + 1, z; (ii) - x + 1, - y + 1, - z + 1; (iii) x, y - 1, z; (iv) - x + 1, - y, - z + 1.]
2-(4-Bromophenyl)-5-fluoro-3-phenylsulfinyl-1-benzofuran top
Crystal data top
C20H12BrFO2SZ = 2
Mr = 415.27F(000) = 416
Triclinic, P1Dx = 1.662 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1361 (4) ÅCell parameters from 8238 reflections
b = 9.8237 (5) Åθ = 2.7–27.5°
c = 11.4093 (5) ŵ = 2.62 mm−1
α = 82.866 (3)°T = 173 K
β = 77.123 (3)°Block, colourless
γ = 69.155 (2)°0.29 × 0.26 × 0.21 mm
V = 829.78 (7) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer		3833 independent reflections
Radiation source: rotating anode3452 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.033
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 1.8°
φ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −12→12
Tmin = 0.664, Tmax = 0.746l = −14→14
14582 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.104H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
3833 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.63 e Å−3
Crystal data top
C20H12BrFO2Sγ = 69.155 (2)°
Mr = 415.27V = 829.78 (7) Å3
Triclinic, P1Z = 2
a = 8.1361 (4) ÅMo Kα radiation
b = 9.8237 (5) ŵ = 2.62 mm−1
c = 11.4093 (5) ÅT = 173 K
α = 82.866 (3)°0.29 × 0.26 × 0.21 mm
β = 77.123 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		3833 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3452 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 0.746Rint = 0.033
14582 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 0.87Δρmax = 0.37 e Å−3
3833 reflectionsΔρmin = −0.63 e Å−3
226 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
xyzUiso*/Ueq
Br−0.21990 (3)0.22528 (2)0.998902 (16)0.03781 (11)
S0.47916 (5)0.16534 (4)0.44461 (4)0.02033 (12)
F0.64982 (17)0.61956 (15)0.12311 (11)0.0381 (3)
O10.17961 (16)0.57103 (13)0.53100 (11)0.0210 (3)
O20.66591 (17)0.14226 (15)0.37795 (13)0.0302 (3)
C10.3705 (2)0.35537 (18)0.46114 (14)0.0193 (3)
C20.4126 (2)0.46848 (19)0.37985 (15)0.0196 (3)
C30.5388 (2)0.4728 (2)0.27522 (16)0.0238 (4)
H30.62340.38850.24130.029*
C40.5298 (2)0.6096 (2)0.22567 (16)0.0264 (4)
C50.4074 (3)0.7387 (2)0.27342 (17)0.0280 (4)
H50.40870.82780.23530.034*
C60.2835 (2)0.7350 (2)0.37772 (16)0.0245 (4)
H60.20040.81970.41210.029*
C70.2906 (2)0.59795 (19)0.42783 (15)0.0201 (3)
C80.2314 (2)0.42188 (17)0.55135 (15)0.0191 (3)
C90.1288 (2)0.37299 (19)0.65891 (15)0.0203 (3)
C10−0.0123 (3)0.4752 (2)0.73078 (17)0.0273 (4)
H10−0.03870.57400.70920.033*
C11−0.1131 (3)0.4322 (2)0.83305 (18)0.0307 (4)
H11−0.20570.50110.88040.037*
C12−0.0740 (2)0.2854 (2)0.86369 (16)0.0256 (4)
C130.0653 (3)0.1814 (2)0.79636 (17)0.0293 (4)
H130.09110.08300.81940.035*
C140.1662 (3)0.2245 (2)0.69446 (17)0.0275 (4)
H140.26000.15460.64880.033*
C150.3563 (2)0.14738 (19)0.33775 (17)0.0217 (3)
C160.1896 (2)0.1320 (2)0.37783 (19)0.0289 (4)
H160.14180.12800.45970.035*
C170.0958 (3)0.1228 (2)0.2932 (2)0.0396 (5)
H17−0.01710.11420.31830.047*
C180.1684 (3)0.1263 (2)0.1723 (2)0.0432 (6)
H180.10410.12040.11640.052*
C190.3370 (4)0.1387 (3)0.1332 (2)0.0461 (6)
H190.38560.14060.05140.055*
C200.4327 (3)0.1481 (2)0.21686 (18)0.0347 (5)
H200.54650.15490.19180.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.03745 (16)0.05065 (18)0.02458 (14)−0.02139 (12)0.00266 (9)0.00468 (10)
S0.0185 (2)0.0151 (2)0.0247 (2)−0.00334 (16)−0.00247 (16)−0.00170 (16)
F0.0399 (7)0.0428 (7)0.0292 (6)−0.0205 (6)0.0043 (5)0.0072 (5)
O10.0219 (6)0.0140 (6)0.0237 (6)−0.0041 (5)−0.0017 (5)0.0004 (4)
O20.0171 (6)0.0280 (7)0.0422 (8)−0.0040 (5)−0.0009 (5)−0.0096 (6)
C10.0199 (8)0.0158 (8)0.0213 (8)−0.0059 (6)−0.0031 (6)0.0000 (6)
C20.0205 (8)0.0188 (8)0.0211 (8)−0.0085 (7)−0.0054 (6)0.0007 (6)
C30.0226 (8)0.0260 (9)0.0225 (8)−0.0097 (7)−0.0014 (7)−0.0012 (7)
C40.0268 (9)0.0325 (10)0.0226 (8)−0.0159 (8)−0.0036 (7)0.0044 (7)
C50.0328 (10)0.0262 (10)0.0292 (9)−0.0154 (8)−0.0113 (8)0.0095 (7)
C60.0265 (9)0.0177 (8)0.0290 (9)−0.0069 (7)−0.0079 (7)0.0025 (7)
C70.0202 (8)0.0198 (8)0.0205 (8)−0.0074 (7)−0.0045 (6)0.0008 (6)
C80.0201 (8)0.0133 (8)0.0235 (8)−0.0047 (6)−0.0058 (6)0.0002 (6)
C90.0198 (8)0.0192 (8)0.0221 (8)−0.0072 (7)−0.0037 (6)−0.0007 (6)
C100.0278 (9)0.0198 (9)0.0285 (9)−0.0040 (7)−0.0009 (7)−0.0012 (7)
C110.0274 (9)0.0302 (10)0.0283 (9)−0.0060 (8)0.0027 (7)−0.0054 (8)
C120.0261 (8)0.0323 (10)0.0191 (8)−0.0131 (8)−0.0015 (7)0.0015 (7)
C130.0345 (10)0.0234 (9)0.0283 (9)−0.0114 (8)−0.0029 (8)0.0040 (7)
C140.0279 (9)0.0197 (9)0.0291 (9)−0.0061 (7)0.0024 (7)−0.0010 (7)
C150.0215 (8)0.0150 (8)0.0283 (9)−0.0054 (7)−0.0053 (7)−0.0012 (6)
C160.0215 (9)0.0227 (9)0.0403 (11)−0.0065 (7)−0.0011 (8)−0.0057 (8)
C170.0263 (9)0.0240 (10)0.0699 (15)−0.0047 (8)−0.0149 (10)−0.0091 (10)
C180.0558 (14)0.0281 (11)0.0552 (14)−0.0124 (10)−0.0337 (12)−0.0003 (10)
C190.0761 (17)0.0456 (14)0.0295 (11)−0.0333 (13)−0.0178 (11)0.0040 (10)
C200.0426 (12)0.0387 (12)0.0288 (10)−0.0246 (10)−0.0018 (9)−0.0005 (8)
Geometric parameters (Å, º) top
Br—C121.8961 (18)C9—C141.406 (2)
S—Si3.2635 (8)C10—C111.382 (3)
S—O21.4903 (13)C10—H100.9300
S—C11.7721 (17)C11—C121.378 (3)
S—C151.7996 (18)C11—H110.9300
F—C41.365 (2)C12—C131.379 (3)
O1—C71.375 (2)C13—C141.380 (3)
O1—C81.3776 (19)C13—H130.9300
C1—C81.374 (2)C14—H140.9300
C1—C21.444 (2)C15—C201.381 (3)
C2—C71.391 (2)C15—C161.387 (2)
C2—C31.397 (2)C16—C171.387 (3)
C3—C41.376 (3)C16—H160.9300
C3—H30.9300C17—C181.375 (4)
C4—C51.389 (3)C17—H170.9300
C5—C61.384 (3)C18—C191.388 (4)
C5—H50.9300C18—H180.9300
C6—C71.382 (2)C19—C201.390 (3)
C6—H60.9300C19—H190.9300
C8—C91.455 (2)C20—H200.9300
C9—C101.401 (2)
O2—S—C1107.56 (8)C11—C10—H10119.3
O2—S—C15106.43 (8)C9—C10—H10119.3
C1—S—C1596.72 (8)C12—C11—C10118.90 (18)
C7—O1—C8106.98 (13)C12—C11—H11120.5
C8—C1—C2107.73 (15)C10—C11—H11120.5
C8—C1—S126.85 (13)C11—C12—C13121.57 (17)
C2—C1—S125.42 (13)C11—C12—Br119.10 (14)
C7—C2—C3119.78 (16)C13—C12—Br119.30 (14)
C7—C2—C1104.55 (14)C12—C13—C14119.45 (18)
C3—C2—C1135.66 (16)C12—C13—H13120.3
C4—C3—C2115.72 (17)C14—C13—H13120.3
C4—C3—H3122.1C13—C14—C9120.77 (18)
C2—C3—H3122.1C13—C14—H14119.6
F—C4—C3117.95 (18)C9—C14—H14119.6
F—C4—C5117.67 (17)C20—C15—C16121.65 (18)
C3—C4—C5124.38 (17)C20—C15—S118.49 (14)
C6—C5—C4120.07 (17)C16—C15—S119.87 (15)
C6—C5—H5120.0C17—C16—C15118.6 (2)
C4—C5—H5120.0C17—C16—H16120.7
C7—C6—C5116.00 (17)C15—C16—H16120.7
C7—C6—H6122.0C18—C17—C16120.5 (2)
C5—C6—H6122.0C18—C17—H17119.8
O1—C7—C6124.94 (16)C16—C17—H17119.8
O1—C7—C2111.03 (14)C17—C18—C19120.6 (2)
C6—C7—C2124.03 (16)C17—C18—H18119.7
C1—C8—O1109.69 (14)C19—C18—H18119.7
C1—C8—C9135.70 (15)C18—C19—C20119.7 (2)
O1—C8—C9114.61 (14)C18—C19—H19120.2
C10—C9—C14117.93 (16)C20—C19—H19120.2
C10—C9—C8119.97 (16)C15—C20—C19119.0 (2)
C14—C9—C8122.10 (16)C15—C20—H20120.5
C11—C10—C9121.35 (17)C19—C20—H20120.5
O2—S—C1—C8−152.47 (14)C7—O1—C8—C9179.29 (13)
C15—S—C1—C897.90 (16)C1—C8—C9—C10−178.05 (18)
O2—S—C1—C228.34 (17)O1—C8—C9—C101.2 (2)
C15—S—C1—C2−81.29 (15)C1—C8—C9—C142.0 (3)
C8—C1—C2—C7−0.77 (18)O1—C8—C9—C14−178.71 (15)
S—C1—C2—C7178.55 (12)C14—C9—C10—C11−0.5 (3)
C8—C1—C2—C3178.37 (18)C8—C9—C10—C11179.57 (17)
S—C1—C2—C3−2.3 (3)C9—C10—C11—C12−0.6 (3)
C7—C2—C3—C4−0.9 (2)C10—C11—C12—C131.5 (3)
C1—C2—C3—C4−179.96 (18)C10—C11—C12—Br−176.61 (14)
C2—C3—C4—F−179.75 (14)C11—C12—C13—C14−1.3 (3)
C2—C3—C4—C50.6 (3)Br—C12—C13—C14176.79 (15)
F—C4—C5—C6−179.58 (15)C12—C13—C14—C90.2 (3)
C3—C4—C5—C60.0 (3)C10—C9—C14—C130.7 (3)
C4—C5—C6—C7−0.4 (2)C8—C9—C14—C13−179.38 (17)
C8—O1—C7—C6−179.14 (16)O2—S—C15—C20−13.32 (18)
C8—O1—C7—C20.74 (17)C1—S—C15—C2097.26 (17)
C5—C6—C7—O1179.97 (15)O2—S—C15—C16166.15 (15)
C5—C6—C7—C20.1 (2)C1—S—C15—C16−83.27 (16)
C3—C2—C7—O1−179.29 (14)C20—C15—C16—C17−2.5 (3)
C1—C2—C7—O10.02 (17)S—C15—C16—C17178.09 (15)
C3—C2—C7—C60.6 (2)C15—C16—C17—C181.1 (3)
C1—C2—C7—C6179.90 (16)C16—C17—C18—C190.2 (3)
C2—C1—C8—O11.26 (18)C17—C18—C19—C20−0.3 (4)
S—C1—C8—O1−178.05 (11)C16—C15—C20—C192.4 (3)
C2—C1—C8—C9−179.43 (17)S—C15—C20—C19−178.13 (17)
S—C1—C8—C91.3 (3)C18—C19—C20—C15−1.0 (4)
C7—O1—C8—C1−1.24 (17)
Symmetry code: (i) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C15–C20 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg3ii0.932.853.644 (3)145
Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H12BrFO2S
Mr415.27
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.1361 (4), 9.8237 (5), 11.4093 (5)
α, β, γ (°)82.866 (3), 77.123 (3), 69.155 (2)
V (Å3)829.78 (7)
Z2
Radiation typeMo Kα
µ (mm−1)2.62
Crystal size (mm)0.29 × 0.26 × 0.21
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.664, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		14582, 3833, 3452
Rint0.033
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.104, 0.87
No. of reflections3833
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.37, −0.63

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
Cg3 is the centroid of the C15–C20 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg3i0.932.853.644 (3)144.5
Symmetry code: (i) x, y+1, z.
 

References

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o2172
https://doi.org/10.1107/S1600536810029958
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