5-Bromo-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(15)H(11)BrO(3)S, was prepared by the oxidation of 5-bromo-2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 78.99 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by C-H⋯π inter-actions between a benzene H atom of the benzofuran unit and the phenyl ring of the phenyl-sulfonyl substituent from a neighbouring mol-ecule. In addition, the crystal structure exhibits intra- and inter-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 5-bromo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶); Seo et al. (2007 ▶).

Experimental

Crystal data

C15H11BrO3S

M = 351.21

Monoclinic,

a = 7.337 (1) Å

b = 11.345 (1) Å

c = 16.602 (2) Å

β = 94.582 (3)°

V = 1377.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.14 mm−1

T = 173 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.463, T max = 0.542

8005 measured reflections

3009 independent reflections

2349 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.03

3009 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.44 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008489/cf2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008489/cf2191Isup2.hkl

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

C15H11BrO3S	F000 = 704
Mr = 351.21	Dx = 1.693 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 3065 reflections
a = 7.337 (1) Å	θ = 2.5–27.7º
b = 11.345 (1) Å	µ = 3.14 mm−1
c = 16.602 (2) Å	T = 173 (2) K
β = 94.582 (3)º	Block, colorless
V = 1377.5 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	2349 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.5º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −14→13
Tmin = 0.463, Tmax = 0.542	l = −14→21
8005 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.6448P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3009 reflections	Δρmax = 0.55 e Å−3
182 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.79772 (5)	0.88457 (2)	0.038216 (19)	0.03963 (12)
S	0.65781 (9)	0.40138 (5)	0.19581 (4)	0.02489 (16)
O1	0.7486 (3)	0.36914 (16)	−0.03375 (11)	0.0296 (4)
O2	0.5677 (3)	0.50746 (16)	0.21839 (12)	0.0327 (5)
O3	0.5740 (3)	0.28903 (15)	0.20838 (12)	0.0344 (5)
C1	0.6960 (4)	0.4145 (2)	0.09406 (16)	0.0242 (5)
C2	0.7309 (3)	0.5236 (2)	0.05267 (15)	0.0227 (5)
C3	0.7410 (4)	0.6429 (2)	0.07353 (16)	0.0255 (5)
H3	0.7209	0.6693	0.1264	0.031*
C4	0.7819 (4)	0.7208 (2)	0.01307 (17)	0.0287 (6)
C5	0.8107 (4)	0.6854 (2)	−0.06521 (16)	0.0305 (6)
H5	0.8372	0.7425	−0.1045	0.037*
C6	0.8010 (4)	0.5675 (3)	−0.08587 (16)	0.0308 (6)
H6	0.8198	0.5412	−0.1389	0.037*
C7	0.7626 (3)	0.4899 (2)	−0.02563 (16)	0.0245 (5)
C8	0.7097 (4)	0.3254 (2)	0.03977 (16)	0.0271 (6)
C9	0.8786 (4)	0.3998 (2)	0.24546 (16)	0.0259 (6)
C10	0.9716 (4)	0.2932 (2)	0.25599 (16)	0.0321 (6)
H10	0.9160	0.2218	0.2368	0.039*
C11	1.1457 (5)	0.2921 (3)	0.29469 (19)	0.0446 (8)
H11	1.2105	0.2200	0.3024	0.054*
C12	1.2249 (5)	0.3974 (3)	0.32221 (19)	0.0506 (9)
H12	1.3445	0.3969	0.3488	0.061*
C13	1.1314 (5)	0.5031 (3)	0.31132 (19)	0.0467 (8)
H13	1.1870	0.5745	0.3304	0.056*
C14	0.9580 (4)	0.5048 (2)	0.27289 (17)	0.0333 (6)
H14	0.8935	0.5771	0.2652	0.040*
C15	0.6972 (4)	0.1947 (2)	0.04402 (19)	0.0374 (7)
H15A	0.8193	0.1605	0.0419	0.056*
H15B	0.6169	0.1657	−0.0017	0.056*
H15C	0.6471	0.1719	0.0947	0.056*

	U11	U22	U33	U12	U13	U23
Br	0.0526 (2)	0.02501 (16)	0.0412 (2)	−0.00489 (13)	0.00320 (14)	0.00437 (12)
S	0.0301 (4)	0.0189 (3)	0.0269 (3)	−0.0004 (2)	0.0096 (3)	0.0010 (2)
O1	0.0328 (11)	0.0301 (10)	0.0263 (10)	0.0005 (8)	0.0042 (8)	−0.0057 (8)
O2	0.0393 (12)	0.0266 (9)	0.0341 (11)	0.0064 (8)	0.0149 (9)	−0.0020 (8)
O3	0.0392 (12)	0.0259 (10)	0.0398 (12)	−0.0066 (8)	0.0140 (9)	0.0038 (8)
C1	0.0256 (14)	0.0230 (12)	0.0246 (13)	0.0000 (10)	0.0059 (11)	−0.0002 (10)
C2	0.0191 (13)	0.0259 (12)	0.0235 (13)	0.0019 (10)	0.0038 (10)	0.0020 (10)
C3	0.0302 (14)	0.0242 (12)	0.0224 (13)	0.0021 (10)	0.0046 (11)	−0.0006 (10)
C4	0.0273 (15)	0.0262 (13)	0.0325 (15)	−0.0024 (11)	0.0019 (12)	0.0024 (11)
C5	0.0288 (15)	0.0371 (15)	0.0258 (14)	0.0000 (12)	0.0039 (11)	0.0081 (12)
C6	0.0296 (15)	0.0427 (15)	0.0202 (14)	0.0016 (12)	0.0033 (11)	−0.0001 (12)
C7	0.0224 (13)	0.0252 (12)	0.0258 (14)	0.0019 (10)	0.0007 (11)	−0.0038 (10)
C8	0.0243 (14)	0.0275 (13)	0.0298 (15)	−0.0014 (11)	0.0032 (11)	−0.0022 (11)
C9	0.0337 (15)	0.0256 (13)	0.0196 (13)	−0.0007 (10)	0.0096 (11)	0.0012 (10)
C10	0.0420 (18)	0.0317 (14)	0.0239 (14)	0.0033 (12)	0.0101 (12)	0.0077 (11)
C11	0.043 (2)	0.059 (2)	0.0330 (17)	0.0144 (16)	0.0095 (14)	0.0149 (15)
C12	0.0376 (19)	0.087 (3)	0.0264 (17)	−0.0062 (18)	0.0010 (14)	0.0063 (17)
C13	0.053 (2)	0.059 (2)	0.0276 (16)	−0.0175 (17)	0.0033 (14)	−0.0068 (15)
C14	0.0444 (18)	0.0305 (14)	0.0258 (14)	−0.0048 (12)	0.0087 (13)	−0.0023 (11)
C15	0.0437 (19)	0.0249 (14)	0.0443 (18)	−0.0021 (12)	0.0074 (14)	−0.0072 (12)

Br—C4	1.906 (3)	C6—H6	0.950
S—O2	1.4372 (18)	C8—C15	1.487 (4)
S—O3	1.4377 (18)	C9—C14	1.387 (4)
S—C1	1.740 (3)	C9—C10	1.393 (4)
S—C9	1.758 (3)	C10—C11	1.383 (4)
O1—C8	1.369 (3)	C10—H10	0.950
O1—C7	1.380 (3)	C11—C12	1.389 (5)
C1—C8	1.363 (4)	C11—H11	0.950
C1—C2	1.448 (3)	C12—C13	1.387 (5)
C2—C7	1.392 (3)	C12—H12	0.950
C2—C3	1.398 (3)	C13—C14	1.377 (4)
C3—C4	1.388 (4)	C13—H13	0.950
C3—H3	0.950	C14—H14	0.950
C4—C5	1.392 (4)	C15—H15A	0.980
C5—C6	1.381 (4)	C15—H15B	0.980
C5—H5	0.950	C15—H15C	0.980
C6—C7	1.378 (4)
O2—S—O3	119.57 (12)	C1—C8—O1	110.7 (2)
O2—S—C1	107.14 (12)	C1—C8—C15	134.4 (3)
O3—S—C1	108.70 (12)	O1—C8—C15	114.9 (2)
O2—S—C9	108.19 (12)	C14—C9—C10	121.1 (3)
O3—S—C9	108.15 (12)	C14—C9—S	119.5 (2)
C1—S—C9	104.02 (12)	C10—C9—S	119.5 (2)
C8—O1—C7	106.97 (19)	C11—C10—C9	119.4 (3)
C8—C1—C2	107.1 (2)	C11—C10—H10	120.3
C8—C1—S	127.2 (2)	C9—C10—H10	120.3
C2—C1—S	125.57 (19)	C10—C11—C12	119.5 (3)
C7—C2—C3	119.2 (2)	C10—C11—H11	120.3
C7—C2—C1	104.9 (2)	C12—C11—H11	120.3
C3—C2—C1	135.9 (2)	C13—C12—C11	120.7 (3)
C4—C3—C2	116.6 (2)	C13—C12—H12	119.6
C4—C3—H3	121.7	C11—C12—H12	119.6
C2—C3—H3	121.7	C14—C13—C12	120.1 (3)
C3—C4—C5	123.3 (2)	C14—C13—H13	119.9
C3—C4—Br	118.4 (2)	C12—C13—H13	119.9
C5—C4—Br	118.32 (19)	C13—C14—C9	119.2 (3)
C6—C5—C4	120.1 (2)	C13—C14—H14	120.4
C6—C5—H5	119.9	C9—C14—H14	120.4
C4—C5—H5	119.9	C8—C15—H15A	109.5
C7—C6—C5	116.6 (2)	C8—C15—H15B	109.5
C7—C6—H6	121.7	H15A—C15—H15B	109.5
C5—C6—H6	121.7	C8—C15—H15C	109.5
C6—C7—O1	125.5 (2)	H15A—C15—H15C	109.5
C6—C7—C2	124.2 (2)	H15B—C15—H15C	109.5
O1—C7—C2	110.3 (2)
O2—S—C1—C8	−152.5 (2)	C3—C2—C7—O1	179.2 (2)
O3—S—C1—C8	−22.0 (3)	C1—C2—C7—O1	0.1 (3)
C9—S—C1—C8	93.1 (3)	C2—C1—C8—O1	−0.8 (3)
O2—S—C1—C2	31.8 (3)	S—C1—C8—O1	−177.14 (19)
O3—S—C1—C2	162.3 (2)	C2—C1—C8—C15	177.1 (3)
C9—S—C1—C2	−82.7 (2)	S—C1—C8—C15	0.8 (5)
C8—C1—C2—C7	0.4 (3)	C7—O1—C8—C1	0.8 (3)
S—C1—C2—C7	176.8 (2)	C7—O1—C8—C15	−177.5 (2)
C8—C1—C2—C3	−178.5 (3)	O2—S—C9—C14	−21.6 (2)
S—C1—C2—C3	−2.0 (5)	O3—S—C9—C14	−152.5 (2)
C7—C2—C3—C4	0.3 (4)	C1—S—C9—C14	92.0 (2)
C1—C2—C3—C4	179.1 (3)	O2—S—C9—C10	158.9 (2)
C2—C3—C4—C5	0.5 (4)	O3—S—C9—C10	28.0 (2)
C2—C3—C4—Br	−179.92 (19)	C1—S—C9—C10	−87.4 (2)
C3—C4—C5—C6	−0.6 (4)	C14—C9—C10—C11	0.2 (4)
Br—C4—C5—C6	179.8 (2)	S—C9—C10—C11	179.7 (2)
C4—C5—C6—C7	−0.2 (4)	C9—C10—C11—C12	−0.2 (4)
C5—C6—C7—O1	−179.4 (2)	C10—C11—C12—C13	0.1 (5)
C5—C6—C7—C2	1.1 (4)	C11—C12—C13—C14	0.0 (5)
C8—O1—C7—C6	179.8 (3)	C12—C13—C14—C9	0.1 (4)
C8—O1—C7—C2	−0.6 (3)	C10—C9—C14—C13	−0.2 (4)
C3—C2—C7—C6	−1.2 (4)	S—C9—C14—C13	−179.6 (2)
C1—C2—C7—C6	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgi	0.95	2.74	3.561 (3)	145
C10—H10···O2ii	0.95	2.54	3.285 (3)	135
C14—H14···O3iii	0.95	2.45	3.249 (3)	141
C15—H15C···O3	0.98	2.40	3.131 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgi	0.95	2.74	3.561 (3)	145
C10—H10⋯O2ii	0.95	2.54	3.285 (3)	135
C14—H14⋯O3iii	0.95	2.45	3.249 (3)	141
C15—H15C⋯O3	0.98	2.40	3.131 (4)	131

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the phenyl ring C9–C14.