5-Bromo-2,4,6-trimethyl-3-phenyl-sulfinyl-1-benzofuran.

The title compound, C(17)H(15)BrO(2)S, which was synthesized by the oxidation of 5-bromo-2,4,6-trimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid, features a trigonally-coordinated S atom. The phenyl ring is approximately perpendicular to the plane of the benzofuran fragment [dihedral angle 75.11 (7)°]. The crystal structure is stabilized by non-classical C-H⋯O and Br⋯Br inter-actions [3.7169 (6) Å].

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Seo et al. (2007 ▶); Choi et al. (2008 ▶).

Experimental

Crystal data

C17H15BrO2S

M = 363.26

Monoclinic,

a = 22.114 (2) Å

b = 10.4281 (8) Å

c = 16.675 (1) Å

β = 125.767 (1)°

V = 3120.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 2.77 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.528, T max = 0.762

8646 measured reflections

3055 independent reflections

2607 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.081

S = 1.05

3055 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.65 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 I. DOI: 10.1107/S160053680802669X/ng2486sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802669X/ng2486Isup2.hkl

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

C17H15BrO2S	F000 = 1472
Mr = 363.26	Dx = 1.547 Mg m−3
Monoclinic, C2/c	Melting point = 446–447 K
Hall symbol: -C_2yc	Mo Kα radiation λ = 0.71073 Å
a = 22.114 (2) Å	Cell parameters from 4364 reflections
b = 10.4281 (8) Å	θ = 2.3–27.6º
c = 16.675 (1) Å	µ = 2.77 mm−1
β = 125.767 (1)º	T = 298 (2) K
V = 3120.1 (4) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Bruker SMART CCD diffractometer	3055 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.015
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 298(2) K	θmin = 3.0º
φ and ω scans	h = −27→26
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −9→12
Tmin = 0.528, Tmax = 0.762	l = −20→19
8646 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0445P)2 + 2.4497P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3055 reflections	Δρmax = 0.29 e Å−3
193 parameters	Δρmin = −0.65 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	0.533506 (16)	0.68321 (3)	0.38143 (2)	0.06177 (12)
S	0.74509 (3)	0.26302 (5)	0.71578 (4)	0.03881 (14)
O1	0.64417 (8)	0.49816 (16)	0.78355 (11)	0.0445 (4)
O2	0.70046 (10)	0.17705 (14)	0.62807 (13)	0.0493 (4)
C1	0.68826 (11)	0.3831 (2)	0.71386 (15)	0.0353 (4)
C2	0.63826 (11)	0.48016 (19)	0.64269 (15)	0.0325 (4)
C3	0.61280 (11)	0.5170 (2)	0.54678 (15)	0.0344 (4)
C4	0.56708 (11)	0.6251 (2)	0.51013 (16)	0.0387 (5)
C5	0.54362 (12)	0.6941 (2)	0.55938 (18)	0.0437 (5)
C6	0.56699 (12)	0.6518 (2)	0.65185 (18)	0.0433 (5)
H6	0.5516	0.6927	0.6866	0.052*
C7	0.61363 (11)	0.5474 (2)	0.69097 (15)	0.0368 (5)
C8	0.68938 (12)	0.3992 (2)	0.79549 (16)	0.0426 (5)
C9	0.80112 (11)	0.3609 (2)	0.69393 (15)	0.0354 (4)
C10	0.81357 (13)	0.3179 (2)	0.62659 (18)	0.0434 (5)
H10	0.7914	0.2426	0.5915	0.052*
C11	0.85940 (14)	0.3879 (3)	0.6117 (2)	0.0549 (6)
H11	0.8672	0.3608	0.5652	0.066*
C12	0.89331 (16)	0.4973 (3)	0.6653 (2)	0.0638 (7)
H12	0.9245	0.5438	0.6558	0.077*
C13	0.88124 (15)	0.5388 (3)	0.7338 (2)	0.0634 (7)
H13	0.9043	0.6132	0.7699	0.076*
C14	0.83519 (13)	0.4705 (2)	0.74880 (17)	0.0477 (6)
H14	0.8272	0.4979	0.7950	0.057*
C15	0.63413 (14)	0.4441 (2)	0.48921 (17)	0.0464 (5)
H15A	0.5921	0.4395	0.4211	0.070*
H15B	0.6494	0.3590	0.5156	0.070*
H15C	0.6745	0.4873	0.4941	0.070*
C16	0.49532 (16)	0.8122 (3)	0.5165 (2)	0.0644 (8)
H16A	0.4891	0.8484	0.5642	0.097*
H16B	0.4475	0.7893	0.4580	0.097*
H16C	0.5187	0.8740	0.5001	0.097*
C17	0.73101 (17)	0.3360 (3)	0.89359 (19)	0.0639 (8)
H17A	0.7592	0.2654	0.8942	0.096*
H17B	0.6965	0.3049	0.9064	0.096*
H17C	0.7643	0.3966	0.9437	0.096*

	U11	U22	U33	U12	U13	U23
Br	0.06404 (19)	0.0623 (2)	0.05692 (18)	0.01291 (13)	0.03418 (15)	0.02859 (12)
S	0.0454 (3)	0.0340 (3)	0.0419 (3)	0.0069 (2)	0.0283 (2)	0.0079 (2)
O1	0.0456 (8)	0.0564 (10)	0.0369 (8)	0.0034 (7)	0.0271 (7)	−0.0034 (7)
O2	0.0603 (10)	0.0352 (8)	0.0607 (11)	−0.0054 (7)	0.0400 (9)	−0.0046 (7)
C1	0.0386 (10)	0.0360 (11)	0.0338 (10)	0.0023 (9)	0.0226 (9)	0.0029 (9)
C2	0.0326 (9)	0.0303 (10)	0.0366 (10)	−0.0017 (8)	0.0214 (9)	−0.0003 (8)
C3	0.0342 (10)	0.0333 (11)	0.0367 (10)	−0.0025 (8)	0.0214 (9)	0.0011 (8)
C4	0.0359 (10)	0.0351 (11)	0.0411 (11)	−0.0027 (9)	0.0203 (9)	0.0058 (9)
C5	0.0334 (11)	0.0353 (12)	0.0542 (14)	−0.0009 (9)	0.0209 (10)	−0.0011 (10)
C6	0.0348 (11)	0.0436 (12)	0.0509 (13)	−0.0014 (9)	0.0247 (10)	−0.0110 (10)
C7	0.0342 (10)	0.0400 (11)	0.0377 (11)	−0.0045 (9)	0.0219 (9)	−0.0047 (9)
C8	0.0443 (11)	0.0491 (13)	0.0372 (11)	0.0020 (10)	0.0254 (10)	0.0040 (10)
C9	0.0354 (10)	0.0327 (10)	0.0371 (11)	0.0051 (8)	0.0206 (9)	0.0033 (9)
C10	0.0488 (13)	0.0405 (12)	0.0452 (12)	−0.0009 (10)	0.0298 (11)	−0.0044 (9)
C11	0.0593 (15)	0.0597 (16)	0.0608 (15)	−0.0007 (13)	0.0437 (13)	0.0003 (13)
C12	0.0615 (16)	0.0614 (17)	0.0824 (19)	−0.0138 (14)	0.0499 (16)	−0.0009 (15)
C13	0.0581 (15)	0.0517 (15)	0.0765 (19)	−0.0172 (13)	0.0371 (15)	−0.0170 (14)
C14	0.0487 (13)	0.0460 (13)	0.0479 (13)	−0.0011 (11)	0.0279 (11)	−0.0100 (10)
C15	0.0559 (13)	0.0511 (14)	0.0396 (12)	0.0086 (11)	0.0320 (11)	0.0078 (10)
C16	0.0557 (15)	0.0468 (15)	0.080 (2)	0.0150 (12)	0.0338 (15)	0.0080 (13)
C17	0.0720 (18)	0.082 (2)	0.0390 (13)	0.0163 (15)	0.0334 (13)	0.0139 (13)

Br—Bri	3.7169 (6)	C9—C14	1.380 (3)
Br—C4	1.914 (2)	C10—C11	1.385 (3)
S—O2	1.4930 (18)	C10—H10	0.9300
S—C1	1.761 (2)	C11—C12	1.371 (4)
S—C9	1.799 (2)	C11—H11	0.9300
O1—C8	1.368 (3)	C12—C13	1.385 (4)
O1—C7	1.373 (3)	C12—H12	0.9300
C1—C8	1.357 (3)	C13—C14	1.380 (4)
C1—C2	1.456 (3)	C13—H13	0.9300
C2—C7	1.396 (3)	C14—H14	0.9300
C2—C3	1.404 (3)	C15—H15A	0.9600
C3—C4	1.394 (3)	C15—H15B	0.9600
C3—C15	1.500 (3)	C15—H15C	0.9600
C4—C5	1.400 (3)	C16—H16A	0.9600
C5—C6	1.382 (4)	C16—H16B	0.9600
C5—C16	1.509 (3)	C16—H16C	0.9600
C6—C7	1.373 (3)	C17—H17A	0.9600
C6—H6	0.9300	C17—H17B	0.9600
C8—C17	1.483 (3)	C17—H17C	0.9600
C9—C10	1.378 (3)
O2—S—C1	110.68 (10)	C9—C10—H10	120.3
O2—S—C9	106.35 (10)	C11—C10—H10	120.3
C1—S—C9	99.28 (10)	C12—C11—C10	120.0 (2)
C8—O1—C7	106.46 (16)	C12—C11—H11	120.0
C8—C1—C2	106.94 (19)	C10—C11—H11	120.0
C8—C1—S	118.37 (17)	C11—C12—C13	120.2 (2)
C2—C1—S	134.65 (15)	C11—C12—H12	119.9
C7—C2—C3	119.17 (19)	C13—C12—H12	119.9
C7—C2—C1	104.22 (17)	C14—C13—C12	120.4 (2)
C3—C2—C1	136.61 (19)	C14—C13—H13	119.8
C4—C3—C2	115.22 (19)	C12—C13—H13	119.8
C4—C3—C15	123.21 (19)	C13—C14—C9	118.8 (2)
C2—C3—C15	121.57 (19)	C13—C14—H14	120.6
C3—C4—C5	125.5 (2)	C9—C14—H14	120.6
C3—C4—Br	117.02 (16)	C3—C15—H15A	109.5
C5—C4—Br	117.45 (16)	C3—C15—H15B	109.5
C6—C5—C4	117.7 (2)	H15A—C15—H15B	109.5
C6—C5—C16	119.3 (2)	C3—C15—H15C	109.5
C4—C5—C16	123.0 (2)	H15A—C15—H15C	109.5
C7—C6—C5	118.1 (2)	H15B—C15—H15C	109.5
C7—C6—H6	121.0	C5—C16—H16A	109.5
C5—C6—H6	121.0	C5—C16—H16B	109.5
O1—C7—C6	124.74 (19)	H16A—C16—H16B	109.5
O1—C7—C2	111.03 (18)	C5—C16—H16C	109.5
C6—C7—C2	124.2 (2)	H16A—C16—H16C	109.5
C1—C8—O1	111.34 (19)	H16B—C16—H16C	109.5
C1—C8—C17	133.4 (2)	C8—C17—H17A	109.5
O1—C8—C17	115.2 (2)	C8—C17—H17B	109.5
C10—C9—C14	121.2 (2)	H17A—C17—H17B	109.5
C10—C9—S	118.02 (17)	C8—C17—H17C	109.5
C14—C9—S	120.60 (17)	H17A—C17—H17C	109.5
C9—C10—C11	119.4 (2)	H17B—C17—H17C	109.5
O2—S—C1—C8	127.65 (18)	C5—C6—C7—O1	176.8 (2)
C9—S—C1—C8	−120.85 (19)	C5—C6—C7—C2	−0.9 (3)
O2—S—C1—C2	−55.0 (2)	C3—C2—C7—O1	179.99 (17)
C9—S—C1—C2	56.5 (2)	C1—C2—C7—O1	−0.4 (2)
C8—C1—C2—C7	0.1 (2)	C3—C2—C7—C6	−2.0 (3)
S—C1—C2—C7	−177.40 (18)	C1—C2—C7—C6	177.5 (2)
C8—C1—C2—C3	179.6 (2)	C2—C1—C8—O1	0.2 (3)
S—C1—C2—C3	2.0 (4)	S—C1—C8—O1	178.23 (15)
C7—C2—C3—C4	3.4 (3)	C2—C1—C8—C17	−177.0 (3)
C1—C2—C3—C4	−176.0 (2)	S—C1—C8—C17	1.1 (4)
C7—C2—C3—C15	−176.74 (19)	C7—O1—C8—C1	−0.5 (2)
C1—C2—C3—C15	3.9 (4)	C7—O1—C8—C17	177.2 (2)
C2—C3—C4—C5	−2.3 (3)	O2—S—C9—C10	−20.6 (2)
C15—C3—C4—C5	177.9 (2)	C1—S—C9—C10	−135.45 (18)
C2—C3—C4—Br	177.91 (14)	O2—S—C9—C14	164.37 (18)
C15—C3—C4—Br	−1.9 (3)	C1—S—C9—C14	49.5 (2)
C3—C4—C5—C6	−0.5 (3)	C14—C9—C10—C11	−1.9 (3)
Br—C4—C5—C6	179.28 (16)	S—C9—C10—C11	−176.89 (19)
C3—C4—C5—C16	178.7 (2)	C9—C10—C11—C12	1.5 (4)
Br—C4—C5—C16	−1.5 (3)	C10—C11—C12—C13	−0.7 (4)
C4—C5—C6—C7	2.1 (3)	C11—C12—C13—C14	0.1 (5)
C16—C5—C6—C7	−177.1 (2)	C12—C13—C14—C9	−0.4 (4)
C8—O1—C7—C6	−177.4 (2)	C10—C9—C14—C13	1.3 (4)
C8—O1—C7—C2	0.6 (2)	S—C9—C14—C13	176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ii	0.93	2.54	3.371 (3)	150
C15—H15A···Br	0.96	2.75	3.118 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.93	2.54	3.371 (3)	150

Symmetry code: (i) .