5-Bromo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(20)H(13)BrO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran system. The S-bound phenyl ring is almost perpendicular to this plane [80.35 (8)°]. The phenyl ring in the 2-position is twisted with respect to the benzofuran plane, making a dihedral angle of 16.0 (1)°.

Related literature

For the crystal structures of similar 5-halo-2-phenyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ▶,b ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products involving a benzofuran ring system, see: Akgul & Anil (2003 ▶); Reuss & König (2004 ▶).

Experimental

Crystal data

C20H13BrO2S

M = 397.27

Triclinic,

a = 8.2670 (1) Å

b = 9.5233 (2) Å

c = 11.8663 (2) Å

α = 72.187 (1)°

β = 80.772 (1)°

γ = 69.526 (1)°

V = 831.76 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.61 mm−1

T = 293 K

0.35 × 0.22 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.462, T max = 0.763

13542 measured reflections

3275 independent reflections

2716 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.05

3275 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039324/dn2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039324/dn2491Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H13BrO2S	Z = 2
Mr = 397.27	F(000) = 400
Triclinic, P1	Dx = 1.586 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2670 (1) Å	Cell parameters from 5885 reflections
b = 9.5233 (2) Å	θ = 2.4–26.0°
c = 11.8663 (2) Å	µ = 2.61 mm−1
α = 72.187 (1)°	T = 293 K
β = 80.772 (1)°	Block, colorless
γ = 69.526 (1)°	0.35 × 0.22 × 0.11 mm
V = 831.76 (2) Å3

Bruker SMART CCD diffractometer	3275 independent reflections
Radiation source: fine-focus sealed tube	2716 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 1.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −11→11
Tmin = 0.462, Tmax = 0.763	l = −14→14
13542 measured reflections

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.095	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3341P] where P = (Fo2 + 2Fc2)/3
3275 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br	1.01046 (4)	0.24078 (4)	0.38069 (3)	0.07875 (15)
S	0.60607 (8)	0.10785 (7)	0.86253 (6)	0.05063 (17)
O1	0.5011 (2)	0.56165 (18)	0.71087 (15)	0.0552 (4)
O2	0.7801 (2)	0.0093 (2)	0.8283 (2)	0.0760 (6)
C1	0.5823 (3)	0.3012 (2)	0.7751 (2)	0.0453 (5)
C2	0.6714 (3)	0.3415 (3)	0.6609 (2)	0.0470 (5)
C3	0.7888 (3)	0.2607 (3)	0.5871 (2)	0.0516 (6)
H3	0.8269	0.1525	0.6070	0.062*
C4	0.8466 (3)	0.3472 (3)	0.4831 (2)	0.0566 (6)
C5	0.7910 (4)	0.5094 (3)	0.4506 (3)	0.0655 (7)
H5	0.8338	0.5632	0.3796	0.079*
C6	0.6738 (4)	0.5895 (3)	0.5225 (3)	0.0645 (7)
H6	0.6343	0.6978	0.5017	0.077*
C7	0.6166 (3)	0.5035 (3)	0.6272 (2)	0.0518 (6)
C8	0.4830 (3)	0.4365 (3)	0.8020 (2)	0.0486 (5)
C9	0.3645 (3)	0.4760 (3)	0.9012 (2)	0.0505 (6)
C10	0.3612 (4)	0.3686 (3)	1.0094 (3)	0.0660 (7)
H10	0.4365	0.2672	1.0207	0.079*
C11	0.2474 (4)	0.4101 (4)	1.1009 (3)	0.0750 (8)
H11	0.2469	0.3363	1.1735	0.090*
C12	0.1352 (4)	0.5581 (4)	1.0866 (3)	0.0768 (9)
H12	0.0581	0.5850	1.1487	0.092*
C13	0.1375 (5)	0.6667 (4)	0.9799 (3)	0.0868 (10)
H13	0.0622	0.7680	0.9696	0.104*
C14	0.2507 (4)	0.6265 (3)	0.8877 (3)	0.0732 (8)
H14	0.2511	0.7011	0.8156	0.088*
C15	0.4515 (3)	0.0742 (2)	0.7931 (2)	0.0455 (5)
C16	0.5017 (4)	0.0001 (3)	0.7038 (3)	0.0647 (7)
H16	0.6170	−0.0307	0.6762	0.078*
C17	0.3767 (6)	−0.0275 (4)	0.6558 (3)	0.0833 (10)
H17	0.4082	−0.0778	0.5959	0.100*
C18	0.2085 (5)	0.0188 (4)	0.6965 (4)	0.0836 (10)
H18	0.1254	0.0015	0.6629	0.100*
C19	0.1600 (4)	0.0901 (4)	0.7856 (4)	0.0791 (10)
H19	0.0445	0.1200	0.8129	0.095*
C20	0.2804 (3)	0.1180 (3)	0.8351 (3)	0.0592 (6)
H20	0.2474	0.1659	0.8964	0.071*

	U11	U22	U33	U12	U13	U23
Br	0.0790 (2)	0.0939 (3)	0.0630 (2)	−0.03538 (18)	0.01864 (16)	−0.02325 (17)
S	0.0434 (3)	0.0442 (3)	0.0520 (4)	−0.0148 (2)	−0.0066 (3)	0.0070 (2)
O1	0.0669 (11)	0.0419 (8)	0.0506 (10)	−0.0212 (8)	−0.0008 (8)	−0.0010 (7)
O2	0.0417 (10)	0.0554 (10)	0.1019 (16)	−0.0060 (8)	−0.0054 (10)	0.0088 (10)
C1	0.0446 (12)	0.0424 (11)	0.0450 (13)	−0.0191 (9)	−0.0066 (10)	0.0017 (9)
C2	0.0452 (12)	0.0475 (12)	0.0462 (13)	−0.0220 (10)	−0.0059 (10)	0.0002 (10)
C3	0.0468 (13)	0.0515 (13)	0.0524 (14)	−0.0201 (10)	−0.0030 (11)	−0.0034 (11)
C4	0.0540 (14)	0.0659 (15)	0.0496 (15)	−0.0267 (12)	0.0013 (11)	−0.0085 (12)
C5	0.0774 (19)	0.0670 (17)	0.0487 (15)	−0.0372 (15)	0.0034 (13)	0.0020 (13)
C6	0.0787 (19)	0.0507 (14)	0.0568 (16)	−0.0289 (13)	−0.0025 (14)	0.0045 (12)
C7	0.0548 (14)	0.0484 (12)	0.0489 (14)	−0.0222 (11)	−0.0026 (11)	−0.0022 (10)
C8	0.0516 (13)	0.0473 (12)	0.0438 (13)	−0.0214 (10)	−0.0071 (10)	0.0008 (10)
C9	0.0501 (13)	0.0527 (13)	0.0490 (14)	−0.0208 (11)	−0.0042 (11)	−0.0085 (11)
C10	0.0787 (19)	0.0550 (15)	0.0548 (16)	−0.0188 (13)	0.0048 (14)	−0.0090 (12)
C11	0.088 (2)	0.0731 (19)	0.0537 (17)	−0.0271 (17)	0.0110 (15)	−0.0100 (14)
C12	0.0691 (19)	0.088 (2)	0.070 (2)	−0.0255 (17)	0.0152 (15)	−0.0269 (17)
C13	0.077 (2)	0.0691 (19)	0.089 (3)	−0.0030 (16)	0.0095 (18)	−0.0164 (18)
C14	0.0709 (19)	0.0611 (16)	0.0660 (19)	−0.0098 (14)	0.0026 (15)	−0.0036 (14)
C15	0.0445 (12)	0.0335 (10)	0.0491 (13)	−0.0121 (9)	−0.0008 (10)	0.0006 (9)
C16	0.0687 (17)	0.0482 (13)	0.0679 (18)	−0.0157 (12)	0.0089 (14)	−0.0125 (12)
C17	0.127 (3)	0.0537 (16)	0.078 (2)	−0.0311 (19)	−0.018 (2)	−0.0209 (15)
C18	0.090 (3)	0.0569 (17)	0.112 (3)	−0.0276 (17)	−0.037 (2)	−0.0142 (18)
C19	0.0525 (17)	0.0681 (18)	0.116 (3)	−0.0219 (14)	−0.0125 (17)	−0.0174 (19)
C20	0.0474 (14)	0.0579 (14)	0.0708 (18)	−0.0168 (11)	0.0004 (12)	−0.0174 (13)

Br—C4	1.899 (3)	C10—C11	1.377 (4)
S—O2	1.489 (2)	C10—H10	0.9300
S—C1	1.775 (2)	C11—C12	1.366 (5)
S—C15	1.789 (2)	C11—H11	0.9300
O1—C7	1.366 (3)	C12—C13	1.371 (5)
O1—C8	1.377 (3)	C12—H12	0.9300
C1—C8	1.365 (4)	C13—C14	1.377 (5)
C1—C2	1.444 (3)	C13—H13	0.9300
C2—C3	1.385 (4)	C14—H14	0.9300
C2—C7	1.391 (3)	C15—C16	1.379 (4)
C3—C4	1.376 (3)	C15—C20	1.383 (3)
C3—H3	0.9300	C16—C17	1.390 (5)
C4—C5	1.393 (4)	C16—H16	0.9300
C5—C6	1.366 (4)	C17—C18	1.359 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.378 (4)	C18—C19	1.361 (5)
C6—H6	0.9300	C18—H18	0.9300
C8—C9	1.459 (4)	C19—C20	1.370 (4)
C9—C10	1.379 (4)	C19—H19	0.9300
C9—C14	1.389 (4)	C20—H20	0.9300
O2—S—C1	106.63 (11)	C11—C10—H10	119.7
O2—S—C15	106.87 (13)	C9—C10—H10	119.7
C1—S—C15	97.41 (10)	C12—C11—C10	120.9 (3)
C7—O1—C8	107.23 (18)	C12—C11—H11	119.6
C8—C1—C2	107.74 (19)	C10—C11—H11	119.6
C8—C1—S	127.74 (19)	C11—C12—C13	119.3 (3)
C2—C1—S	124.50 (18)	C11—C12—H12	120.3
C3—C2—C7	119.5 (2)	C13—C12—H12	120.3
C3—C2—C1	136.0 (2)	C12—C13—C14	120.3 (3)
C7—C2—C1	104.5 (2)	C12—C13—H13	119.9
C4—C3—C2	117.2 (2)	C14—C13—H13	119.9
C4—C3—H3	121.4	C13—C14—C9	120.8 (3)
C2—C3—H3	121.4	C13—C14—H14	119.6
C3—C4—C5	122.7 (3)	C9—C14—H14	119.6
C3—C4—Br	118.6 (2)	C16—C15—C20	120.5 (3)
C5—C4—Br	118.8 (2)	C16—C15—S	121.3 (2)
C6—C5—C4	120.3 (2)	C20—C15—S	118.1 (2)
C6—C5—H5	119.9	C15—C16—C17	118.8 (3)
C4—C5—H5	119.9	C15—C16—H16	120.6
C5—C6—C7	117.3 (2)	C17—C16—H16	120.6
C5—C6—H6	121.4	C18—C17—C16	120.1 (3)
C7—C6—H6	121.4	C18—C17—H17	120.0
O1—C7—C6	126.1 (2)	C16—C17—H17	120.0
O1—C7—C2	110.8 (2)	C17—C18—C19	120.9 (3)
C6—C7—C2	123.0 (3)	C17—C18—H18	119.5
C1—C8—O1	109.7 (2)	C19—C18—H18	119.5
C1—C8—C9	135.1 (2)	C18—C19—C20	120.3 (3)
O1—C8—C9	115.3 (2)	C18—C19—H19	119.8
C10—C9—C14	118.1 (3)	C20—C19—H19	119.8
C10—C9—C8	122.2 (2)	C19—C20—C15	119.3 (3)
C14—C9—C8	119.6 (2)	C19—C20—H20	120.3
C11—C10—C9	120.6 (3)	C15—C20—H20	120.3
O2—S—C1—C8	−152.9 (2)	C7—O1—C8—C1	−1.4 (3)
C15—S—C1—C8	96.9 (2)	C7—O1—C8—C9	179.5 (2)
O2—S—C1—C2	25.7 (2)	C1—C8—C9—C10	16.4 (5)
C15—S—C1—C2	−84.4 (2)	O1—C8—C9—C10	−164.9 (2)
C8—C1—C2—C3	179.1 (3)	C1—C8—C9—C14	−163.9 (3)
S—C1—C2—C3	0.2 (4)	O1—C8—C9—C14	14.8 (4)
C8—C1—C2—C7	0.1 (3)	C14—C9—C10—C11	0.3 (5)
S—C1—C2—C7	−178.80 (18)	C8—C9—C10—C11	−180.0 (3)
C7—C2—C3—C4	0.5 (4)	C9—C10—C11—C12	0.1 (5)
C1—C2—C3—C4	−178.4 (3)	C10—C11—C12—C13	−0.6 (6)
C2—C3—C4—C5	−0.4 (4)	C11—C12—C13—C14	0.6 (6)
C2—C3—C4—Br	179.02 (18)	C12—C13—C14—C9	−0.1 (6)
C3—C4—C5—C6	−0.3 (4)	C10—C9—C14—C13	−0.3 (5)
Br—C4—C5—C6	−179.7 (2)	C8—C9—C14—C13	179.9 (3)
C4—C5—C6—C7	0.8 (4)	O2—S—C15—C16	−14.1 (2)
C8—O1—C7—C6	−178.7 (3)	C1—S—C15—C16	95.8 (2)
C8—O1—C7—C2	1.5 (3)	O2—S—C15—C20	162.89 (18)
C5—C6—C7—O1	179.6 (3)	C1—S—C15—C20	−87.2 (2)
C5—C6—C7—C2	−0.7 (4)	C20—C15—C16—C17	0.9 (4)
C3—C2—C7—O1	179.8 (2)	S—C15—C16—C17	177.9 (2)
C1—C2—C7—O1	−1.0 (3)	C15—C16—C17—C18	0.3 (4)
C3—C2—C7—C6	0.0 (4)	C16—C17—C18—C19	−1.2 (5)
C1—C2—C7—C6	179.2 (3)	C17—C18—C19—C20	0.7 (5)
C2—C1—C8—O1	0.9 (3)	C18—C19—C20—C15	0.5 (5)
S—C1—C8—O1	179.67 (17)	C16—C15—C20—C19	−1.3 (4)
C2—C1—C8—C9	179.6 (3)	S—C15—C20—C19	−178.4 (2)
S—C1—C8—C9	−1.6 (4)