5-Bromo-7-methyl-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C17H15BrO2S, the 4-methyl-phenyl ring makes a dihedral angle of 14.46 (5)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by pairs of Br⋯O contacts [3.151 (2) Å] into centrosymmetric dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶); Seo et al. (2009 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Triclinic,

a = 7.6375 (2) Å

b = 9.5170 (2) Å

c = 11.2413 (2) Å

α = 75.513 (1)°

β = 84.848 (1)°

γ = 71.626 (1)°

V = 750.72 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.88 mm−1

T = 173 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.504, T max = 0.568

14012 measured reflections

3716 independent reflections

3331 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.075

S = 1.05

3716 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.56 e Å−3

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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204682X/rz5021sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204682X/rz5021Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204682X/rz5021Isup3.cml

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

C17H15BrO2S	Z = 2
Mr = 363.26	F(000) = 368
Triclinic, P1	Dx = 1.607 Mg m−3
Hall symbol: -P 1	Melting point = 462–463 K
a = 7.6375 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5170 (2) Å	Cell parameters from 6280 reflections
c = 11.2413 (2) Å	θ = 2.6–28.3°
α = 75.513 (1)°	µ = 2.88 mm−1
β = 84.848 (1)°	T = 173 K
γ = 71.626 (1)°	Block, colourless
V = 750.72 (3) Å3	0.28 × 0.24 × 0.22 mm

Bruker SMART APEXII CCD diffractometer	3716 independent reflections
Radiation source: rotating anode	3331 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.040
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.504, Tmax = 0.568	l = −14→14
14012 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F2) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.039P)2 + 0.174P] where P = (Fo2 + 2Fc2)/3
3716 reflections	(Δ/σ)max = 0.002
193 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.56 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
Br1	1.01640 (2)	0.25733 (2)	1.044940 (18)	0.03262 (8)
S1	0.65991 (7)	0.79517 (5)	0.61463 (5)	0.03608 (13)
O1	0.80729 (16)	0.39887 (14)	0.52060 (12)	0.0266 (3)
O2	0.7824 (3)	0.80345 (17)	0.70610 (17)	0.0516 (4)
C1	0.7300 (2)	0.60520 (19)	0.60028 (18)	0.0262 (4)
C2	0.8166 (2)	0.47429 (19)	0.69618 (17)	0.0247 (3)
C3	0.8598 (2)	0.44924 (19)	0.81916 (18)	0.0270 (4)
H3	0.8304	0.5300	0.8601	0.032*
C6	0.9504 (2)	0.2018 (2)	0.69871 (19)	0.0278 (4)
C10	0.6566 (2)	0.6248 (2)	0.37333 (17)	0.0258 (3)
C4	0.9481 (2)	0.3001 (2)	0.87834 (18)	0.0265 (4)
C14	0.6396 (3)	0.6087 (2)	0.16459 (19)	0.0339 (4)
H14	0.6760	0.5516	0.1034	0.041*
C5	0.9929 (2)	0.1788 (2)	0.82077 (18)	0.0285 (4)
H5	1.0535	0.0787	0.8661	0.034*
C8	0.7269 (2)	0.55446 (19)	0.49709 (17)	0.0251 (3)
C7	0.8620 (2)	0.35210 (19)	0.64087 (17)	0.0244 (3)
C12	0.4659 (3)	0.8359 (2)	0.22513 (19)	0.0322 (4)
H12	0.3837	0.9368	0.2061	0.039*
C13	0.5173 (2)	0.7551 (2)	0.13389 (19)	0.0315 (4)
C11	0.5323 (3)	0.7721 (2)	0.34314 (19)	0.0310 (4)
H11	0.4931	0.8286	0.4045	0.037*
C15	0.7097 (3)	0.5440 (2)	0.28117 (19)	0.0306 (4)
H15	0.7943	0.4441	0.2990	0.037*
C16	0.4439 (3)	0.8233 (3)	0.0066 (2)	0.0401 (5)
H16A	0.3579	0.9255	0.0027	0.060*
H16B	0.3794	0.7591	−0.0149	0.060*
H16C	0.5464	0.8300	−0.0514	0.060*
C9	0.9909 (3)	0.0770 (2)	0.6320 (2)	0.0389 (5)
H9A	1.0309	−0.0220	0.6908	0.058*
H9B	1.0890	0.0862	0.5708	0.058*
H9C	0.8793	0.0850	0.5907	0.058*
C17	0.4442 (3)	0.7945 (3)	0.6906 (2)	0.0482 (6)
H17A	0.4645	0.7094	0.7633	0.072*
H17B	0.3613	0.7832	0.6344	0.072*
H17C	0.3884	0.8906	0.7158	0.072*

	U11	U22	U33	U12	U13	U23
Br1	0.04139 (12)	0.03114 (11)	0.02435 (12)	−0.01163 (8)	−0.01237 (8)	0.00023 (8)
S1	0.0551 (3)	0.0203 (2)	0.0333 (3)	−0.01144 (19)	−0.0163 (2)	−0.00163 (19)
O1	0.0316 (6)	0.0258 (6)	0.0205 (7)	−0.0063 (5)	−0.0039 (5)	−0.0037 (5)
O2	0.0753 (11)	0.0340 (8)	0.0538 (11)	−0.0211 (7)	−0.0298 (9)	−0.0090 (7)
C1	0.0327 (8)	0.0213 (7)	0.0247 (10)	−0.0096 (6)	−0.0067 (7)	−0.0014 (7)
C2	0.0276 (8)	0.0232 (8)	0.0234 (10)	−0.0095 (6)	−0.0055 (7)	−0.0016 (7)
C3	0.0328 (8)	0.0251 (8)	0.0247 (10)	−0.0104 (7)	−0.0067 (7)	−0.0042 (7)
C6	0.0272 (8)	0.0256 (8)	0.0288 (10)	−0.0046 (6)	−0.0037 (7)	−0.0062 (7)
C10	0.0283 (8)	0.0292 (8)	0.0202 (9)	−0.0124 (7)	−0.0042 (7)	−0.0004 (7)
C4	0.0289 (8)	0.0295 (8)	0.0211 (9)	−0.0106 (7)	−0.0076 (7)	−0.0013 (7)
C14	0.0405 (10)	0.0418 (10)	0.0217 (10)	−0.0152 (8)	−0.0013 (8)	−0.0078 (8)
C5	0.0294 (8)	0.0248 (8)	0.0283 (10)	−0.0066 (6)	−0.0069 (7)	−0.0008 (7)
C8	0.0261 (8)	0.0243 (8)	0.0243 (10)	−0.0089 (6)	−0.0033 (7)	−0.0018 (7)
C7	0.0260 (8)	0.0261 (8)	0.0209 (9)	−0.0081 (6)	−0.0034 (6)	−0.0038 (7)
C12	0.0337 (9)	0.0334 (9)	0.0261 (11)	−0.0093 (7)	−0.0065 (8)	0.0000 (8)
C13	0.0312 (9)	0.0429 (10)	0.0215 (10)	−0.0172 (8)	−0.0055 (7)	0.0001 (8)
C11	0.0362 (9)	0.0313 (9)	0.0238 (10)	−0.0088 (7)	−0.0048 (7)	−0.0037 (8)
C15	0.0331 (9)	0.0319 (9)	0.0256 (10)	−0.0098 (7)	−0.0019 (7)	−0.0042 (8)
C16	0.0398 (10)	0.0549 (13)	0.0250 (11)	−0.0181 (9)	−0.0075 (8)	−0.0009 (10)
C9	0.0461 (11)	0.0272 (9)	0.0374 (13)	0.0001 (8)	−0.0038 (9)	−0.0103 (9)
C17	0.0543 (13)	0.0416 (12)	0.0459 (15)	−0.0019 (10)	−0.0051 (11)	−0.0202 (11)

Br1—C4	1.8987 (19)	C14—C15	1.377 (3)
Br1—O2i	3.1514 (17)	C14—C13	1.389 (3)
S1—O2	1.4825 (16)	C14—H14	0.9500
S1—C1	1.7611 (17)	C5—H5	0.9500
S1—C17	1.787 (3)	C12—C11	1.382 (3)
O1—C7	1.372 (2)	C12—C13	1.389 (3)
O1—C8	1.378 (2)	C12—H12	0.9500
C1—C8	1.368 (3)	C13—C16	1.494 (3)
C1—C2	1.445 (2)	C11—H11	0.9500
C2—C7	1.388 (2)	C15—H15	0.9500
C2—C3	1.395 (3)	C16—H16A	0.9800
C3—C4	1.385 (2)	C16—H16B	0.9800
C3—H3	0.9500	C16—H16C	0.9800
C6—C5	1.386 (3)	C9—H9A	0.9800
C6—C7	1.389 (2)	C9—H9B	0.9800
C6—C9	1.497 (3)	C9—H9C	0.9800
C10—C15	1.398 (3)	C17—H17A	0.9800
C10—C11	1.401 (3)	C17—H17B	0.9800
C10—C8	1.454 (3)	C17—H17C	0.9800
C4—C5	1.398 (3)
C4—Br1—O2i	166.55 (6)	O1—C7—C6	123.97 (16)
O2—S1—C1	106.92 (9)	C2—C7—C6	124.96 (18)
O2—S1—C17	106.93 (12)	C11—C12—C13	121.09 (18)
C1—S1—C17	97.14 (10)	C11—C12—H12	119.5
C7—O1—C8	106.78 (13)	C13—C12—H12	119.5
C8—C1—C2	107.54 (15)	C12—C13—C14	117.90 (18)
C8—C1—S1	127.55 (14)	C12—C13—C16	121.17 (18)
C2—C1—S1	124.74 (14)	C14—C13—C16	120.94 (19)
C7—C2—C3	119.56 (16)	C12—C11—C10	120.76 (19)
C7—C2—C1	104.61 (16)	C12—C11—H11	119.6
C3—C2—C1	135.82 (17)	C10—C11—H11	119.6
C4—C3—C2	116.29 (16)	C14—C15—C10	120.27 (18)
C4—C3—H3	121.9	C14—C15—H15	119.9
C2—C3—H3	121.9	C10—C15—H15	119.9
C5—C6—C7	114.80 (16)	C13—C16—H16A	109.5
C5—C6—C9	124.04 (17)	C13—C16—H16B	109.5
C7—C6—C9	121.14 (18)	H16A—C16—H16B	109.5
C15—C10—C11	118.12 (18)	C13—C16—H16C	109.5
C15—C10—C8	120.06 (16)	H16A—C16—H16C	109.5
C11—C10—C8	121.81 (17)	H16B—C16—H16C	109.5
C3—C4—C5	123.18 (18)	C6—C9—H9A	109.5
C3—C4—Br1	118.81 (14)	C6—C9—H9B	109.5
C5—C4—Br1	118.00 (13)	H9A—C9—H9B	109.5
C15—C14—C13	121.86 (19)	C6—C9—H9C	109.5
C15—C14—H14	119.1	H9A—C9—H9C	109.5
C13—C14—H14	119.1	H9B—C9—H9C	109.5
C6—C5—C4	121.20 (16)	S1—C17—H17A	109.5
C6—C5—H5	119.4	S1—C17—H17B	109.5
C4—C5—H5	119.4	H17A—C17—H17B	109.5
C1—C8—O1	109.99 (15)	S1—C17—H17C	109.5
C1—C8—C10	135.25 (16)	H17A—C17—H17C	109.5
O1—C8—C10	114.74 (15)	H17B—C17—H17C	109.5
O1—C7—C2	111.07 (15)
O2—S1—C1—C8	−146.49 (17)	C15—C10—C8—C1	166.89 (19)
C17—S1—C1—C8	103.34 (18)	C11—C10—C8—C1	−14.6 (3)
O2—S1—C1—C2	28.10 (19)	C15—C10—C8—O1	−14.8 (2)
C17—S1—C1—C2	−82.07 (17)	C11—C10—C8—O1	163.75 (15)
C8—C1—C2—C7	0.78 (19)	C8—O1—C7—C2	0.72 (18)
S1—C1—C2—C7	−174.73 (13)	C8—O1—C7—C6	−179.55 (16)
C8—C1—C2—C3	−179.73 (19)	C3—C2—C7—O1	179.48 (14)
S1—C1—C2—C3	4.8 (3)	C1—C2—C7—O1	−0.92 (19)
C7—C2—C3—C4	0.3 (2)	C3—C2—C7—C6	−0.2 (3)
C1—C2—C3—C4	−179.18 (19)	C1—C2—C7—C6	179.35 (16)
C2—C3—C4—C5	−0.2 (3)	C5—C6—C7—O1	−179.58 (15)
C2—C3—C4—Br1	178.66 (12)	C9—C6—C7—O1	−0.8 (3)
O2i—Br1—C4—C3	−92.2 (3)	C5—C6—C7—C2	0.1 (3)
O2i—Br1—C4—C5	86.6 (3)	C9—C6—C7—C2	178.91 (18)
C7—C6—C5—C4	0.0 (3)	C11—C12—C13—C14	−0.9 (3)
C9—C6—C5—C4	−178.76 (18)	C11—C12—C13—C16	179.26 (18)
C3—C4—C5—C6	0.0 (3)	C15—C14—C13—C12	−0.2 (3)
Br1—C4—C5—C6	−178.79 (13)	C15—C14—C13—C16	179.66 (18)
C2—C1—C8—O1	−0.37 (19)	C13—C12—C11—C10	1.4 (3)
S1—C1—C8—O1	174.97 (13)	C15—C10—C11—C12	−0.8 (3)
C2—C1—C8—C10	178.02 (18)	C8—C10—C11—C12	−179.30 (16)
S1—C1—C8—C10	−6.6 (3)	C13—C14—C15—C10	0.8 (3)
C7—O1—C8—C1	−0.20 (18)	C11—C10—C15—C14	−0.3 (3)
C7—O1—C8—C10	−178.95 (14)	C8—C10—C15—C14	178.27 (16)