3-(4-Bromo-phenyl-sulfin-yl)-2,4,6,7-tetra-methyl-1-benzofuran.

In the title compound, C(18)H(17)BrO(2)S, the 4-bromo-phenyl ring makes a dihedral angle of 89.03 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C18H17BrO2S

M = 377.29

Orthorhombic,

a = 12.0900 (4) Å

b = 20.8119 (10) Å

c = 6.4865 (2) Å

V = 1632.11 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.65 mm−1

T = 173 K

0.28 × 0.27 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.524, T max = 0.857

8826 measured reflections

3658 independent reflections

2943 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.076

S = 0.99

3658 reflections

203 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1607 Friedel pairs

Flack parameter: 0.005 (8)

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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001973/xu5447sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001973/xu5447Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001973/xu5447Isup3.cml

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

C18H17BrO2S	F(000) = 768
Mr = 377.29	Dx = 1.535 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3034 reflections
a = 12.0900 (4) Å	θ = 2.6–26.5°
b = 20.8119 (10) Å	µ = 2.65 mm−1
c = 6.4865 (2) Å	T = 173 K
V = 1632.11 (11) Å3	Block, colourless
Z = 4	0.28 × 0.27 × 0.06 mm

Bruker SMART APEXII CCD diffractometer	3658 independent reflections
Radiation source: rotating anode	2943 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.037
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→27
Tmin = 0.524, Tmax = 0.857	l = −8→8
8826 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0182P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3658 reflections	Δρmax = 0.29 e Å−3
203 parameters	Δρmin = −0.29 e Å−3
1 restraint	Absolute structure: Flack (1983), 1607 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.005 (8)

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	0.48579 (2)	0.445878 (18)	−0.20739 (7)	0.05430 (12)
S1	0.36475 (5)	0.25057 (4)	0.52550 (12)	0.03236 (16)
O1	0.62687 (13)	0.14452 (9)	0.6057 (3)	0.0293 (4)
O2	0.25673 (14)	0.22004 (11)	0.4737 (3)	0.0426 (5)
C1	0.47176 (18)	0.19373 (14)	0.5032 (4)	0.0265 (6)
C2	0.49653 (18)	0.14497 (14)	0.3496 (4)	0.0271 (6)
C3	0.4518 (2)	0.12236 (13)	0.1632 (4)	0.0296 (6)
C4	0.5086 (2)	0.07291 (16)	0.0671 (5)	0.0341 (7)
H4	0.4800	0.0571	−0.0597	0.041*
C5	0.6055 (2)	0.04454 (13)	0.1445 (4)	0.0321 (6)
C6	0.6495 (2)	0.06553 (13)	0.3332 (4)	0.0302 (6)
C7	0.5935 (2)	0.11587 (13)	0.4230 (4)	0.0263 (6)
C8	0.5520 (2)	0.19176 (13)	0.6489 (4)	0.0275 (6)
C9	0.3473 (2)	0.14958 (16)	0.0704 (4)	0.0373 (7)
H9A	0.3632	0.1916	0.0091	0.056*
H9B	0.2912	0.1544	0.1783	0.056*
H9C	0.3198	0.1204	−0.0364	0.056*
C10	0.6606 (2)	−0.00863 (15)	0.0254 (5)	0.0460 (8)
H10A	0.7390	0.0017	0.0058	0.069*
H10B	0.6247	−0.0132	−0.1093	0.069*
H10C	0.6539	−0.0490	0.1021	0.069*
C11	0.7512 (2)	0.03784 (15)	0.4304 (5)	0.0401 (7)
H11A	0.7537	0.0499	0.5763	0.060*
H11B	0.8169	0.0546	0.3601	0.060*
H11C	0.7496	−0.0091	0.4183	0.060*
C12	0.5771 (2)	0.23122 (14)	0.8323 (4)	0.0341 (6)
H12A	0.5872	0.2032	0.9521	0.051*
H12B	0.5157	0.2609	0.8583	0.051*
H12C	0.6450	0.2558	0.8081	0.051*
C13	0.40119 (18)	0.30180 (12)	0.3141 (4)	0.0280 (6)
C14	0.32284 (19)	0.31628 (13)	0.1674 (4)	0.0304 (6)
H14	0.2519	0.2968	0.1740	0.036*
C15	0.3471 (2)	0.35925 (14)	0.0098 (5)	0.0325 (6)
H15	0.2940	0.3689	−0.0936	0.039*
C16	0.4504 (2)	0.38754 (13)	0.0075 (4)	0.0336 (6)
C17	0.5294 (2)	0.37388 (14)	0.1551 (5)	0.0351 (7)
H17	0.5999	0.3939	0.1497	0.042*
C18	0.50500 (18)	0.33121 (14)	0.3091 (6)	0.0328 (6)
H18	0.5584	0.3217	0.4121	0.039*

	U11	U22	U33	U12	U13	U23
Br1	0.04980 (18)	0.0588 (2)	0.0543 (2)	−0.01458 (15)	−0.0108 (2)	0.0187 (2)
S1	0.0254 (3)	0.0424 (4)	0.0292 (3)	0.0041 (3)	0.0027 (3)	−0.0035 (3)
O1	0.0267 (8)	0.0342 (11)	0.0269 (9)	0.0003 (8)	−0.0012 (8)	−0.0024 (8)
O2	0.0204 (8)	0.0585 (15)	0.0490 (13)	−0.0016 (8)	0.0056 (8)	0.0010 (11)
C1	0.0225 (11)	0.0324 (16)	0.0246 (13)	−0.0003 (10)	0.0043 (11)	−0.0007 (11)
C2	0.0235 (12)	0.0294 (17)	0.0283 (15)	−0.0036 (10)	0.0051 (10)	0.0010 (11)
C3	0.0284 (12)	0.0340 (17)	0.0264 (13)	−0.0081 (11)	−0.0011 (11)	0.0028 (13)
C4	0.0385 (15)	0.0387 (18)	0.0251 (14)	−0.0125 (13)	0.0008 (11)	−0.0040 (13)
C5	0.0363 (14)	0.0261 (16)	0.0339 (15)	−0.0072 (11)	0.0089 (13)	−0.0038 (12)
C6	0.0291 (12)	0.0292 (17)	0.0323 (16)	−0.0045 (10)	0.0028 (11)	0.0014 (13)
C7	0.0265 (12)	0.0309 (16)	0.0214 (12)	−0.0037 (11)	0.0010 (11)	−0.0007 (11)
C8	0.0267 (12)	0.0309 (16)	0.0249 (14)	0.0002 (11)	0.0017 (11)	0.0017 (12)
C9	0.0327 (13)	0.049 (2)	0.0299 (15)	−0.0067 (13)	−0.0065 (12)	−0.0059 (13)
C10	0.0533 (18)	0.040 (2)	0.0448 (16)	−0.0017 (14)	0.0079 (18)	−0.0112 (16)
C11	0.0357 (14)	0.0355 (19)	0.0490 (18)	0.0064 (13)	−0.0006 (14)	−0.0014 (15)
C12	0.0318 (14)	0.0416 (18)	0.0288 (15)	0.0003 (12)	−0.0011 (12)	−0.0052 (13)
C13	0.0234 (10)	0.0303 (15)	0.0304 (14)	0.0065 (10)	−0.0005 (12)	−0.0068 (13)
C14	0.0219 (11)	0.0340 (17)	0.0351 (15)	0.0023 (11)	−0.0029 (12)	−0.0059 (13)
C15	0.0238 (12)	0.0369 (18)	0.0369 (15)	0.0039 (11)	−0.0055 (12)	−0.0041 (14)
C16	0.0370 (13)	0.0303 (17)	0.0335 (15)	−0.0001 (12)	−0.0020 (13)	−0.0030 (14)
C17	0.0247 (12)	0.0347 (18)	0.0459 (18)	−0.0028 (12)	−0.0009 (13)	−0.0036 (14)
C18	0.0262 (12)	0.0350 (17)	0.0371 (16)	0.0046 (10)	−0.0061 (14)	−0.0006 (16)

Br1—C16	1.897 (3)	C9—H9C	0.9800
S1—O2	1.491 (2)	C10—H10A	0.9800
S1—C1	1.759 (3)	C10—H10B	0.9800
S1—C13	1.792 (3)	C10—H10C	0.9800
O1—C8	1.365 (3)	C11—H11A	0.9800
O1—C7	1.387 (3)	C11—H11B	0.9800
C1—C8	1.355 (4)	C11—H11C	0.9800
C1—C2	1.453 (4)	C12—H12A	0.9800
C2—C7	1.403 (4)	C12—H12B	0.9800
C2—C3	1.405 (4)	C12—H12C	0.9800
C3—C4	1.385 (4)	C13—C14	1.376 (4)
C3—C9	1.510 (4)	C13—C18	1.397 (3)
C4—C5	1.406 (4)	C14—C15	1.390 (4)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.404 (4)	C15—C16	1.381 (4)
C5—C10	1.505 (4)	C15—H15	0.9500
C6—C7	1.377 (4)	C16—C17	1.381 (4)
C6—C11	1.497 (4)	C17—C18	1.369 (5)
C8—C12	1.477 (4)	C17—H17	0.9500
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800
O2—S1—C1	109.82 (13)	C5—C10—H10B	109.5
O2—S1—C13	107.25 (12)	H10A—C10—H10B	109.5
C1—S1—C13	99.00 (12)	C5—C10—H10C	109.5
C8—O1—C7	107.00 (19)	H10A—C10—H10C	109.5
C8—C1—C2	108.0 (2)	H10B—C10—H10C	109.5
C8—C1—S1	119.3 (2)	C6—C11—H11A	109.5
C2—C1—S1	132.64 (19)	C6—C11—H11B	109.5
C7—C2—C3	118.0 (3)	H11A—C11—H11B	109.5
C7—C2—C1	103.9 (2)	C6—C11—H11C	109.5
C3—C2—C1	138.1 (2)	H11A—C11—H11C	109.5
C4—C3—C2	116.5 (2)	H11B—C11—H11C	109.5
C4—C3—C9	120.9 (3)	C8—C12—H12A	109.5
C2—C3—C9	122.6 (3)	C8—C12—H12B	109.5
C3—C4—C5	124.3 (3)	H12A—C12—H12B	109.5
C3—C4—H4	117.8	C8—C12—H12C	109.5
C5—C4—H4	117.8	H12A—C12—H12C	109.5
C6—C5—C4	119.8 (3)	H12B—C12—H12C	109.5
C6—C5—C10	120.6 (3)	C14—C13—C18	120.4 (3)
C4—C5—C10	119.6 (3)	C14—C13—S1	119.35 (18)
C7—C6—C5	114.8 (2)	C18—C13—S1	120.0 (2)
C7—C6—C11	121.3 (2)	C13—C14—C15	120.3 (2)
C5—C6—C11	123.9 (2)	C13—C14—H14	119.8
C6—C7—O1	123.1 (2)	C15—C14—H14	119.8
C6—C7—C2	126.6 (2)	C16—C15—C14	118.2 (2)
O1—C7—C2	110.3 (2)	C16—C15—H15	120.9
C1—C8—O1	110.7 (2)	C14—C15—H15	120.9
C1—C8—C12	133.8 (2)	C17—C16—C15	122.0 (3)
O1—C8—C12	115.5 (2)	C17—C16—Br1	119.0 (2)
C3—C9—H9A	109.5	C15—C16—Br1	119.0 (2)
C3—C9—H9B	109.5	C18—C17—C16	119.4 (2)
H9A—C9—H9B	109.5	C18—C17—H17	120.3
C3—C9—H9C	109.5	C16—C17—H17	120.3
H9A—C9—H9C	109.5	C17—C18—C13	119.6 (3)
H9B—C9—H9C	109.5	C17—C18—H18	120.2
C5—C10—H10A	109.5	C13—C18—H18	120.2
O2—S1—C1—C8	−137.6 (2)	C8—O1—C7—C2	−0.2 (3)
C13—S1—C1—C8	110.3 (2)	C3—C2—C7—C6	−1.6 (4)
O2—S1—C1—C2	43.6 (3)	C1—C2—C7—C6	178.7 (3)
C13—S1—C1—C2	−68.5 (3)	C3—C2—C7—O1	179.1 (2)
C8—C1—C2—C7	1.1 (3)	C1—C2—C7—O1	−0.5 (3)
S1—C1—C2—C7	−180.0 (2)	C2—C1—C8—O1	−1.3 (3)
C8—C1—C2—C3	−178.5 (3)	S1—C1—C8—O1	179.65 (18)
S1—C1—C2—C3	0.4 (5)	C2—C1—C8—C12	175.0 (3)
C7—C2—C3—C4	−0.3 (4)	S1—C1—C8—C12	−4.1 (4)
C1—C2—C3—C4	179.2 (3)	C7—O1—C8—C1	0.9 (3)
C7—C2—C3—C9	179.5 (2)	C7—O1—C8—C12	−176.1 (2)
C1—C2—C3—C9	−1.0 (5)	O2—S1—C13—C14	13.0 (2)
C2—C3—C4—C5	0.5 (4)	C1—S1—C13—C14	127.2 (2)
C9—C3—C4—C5	−179.3 (3)	O2—S1—C13—C18	−172.7 (2)
C3—C4—C5—C6	1.2 (4)	C1—S1—C13—C18	−58.6 (2)
C3—C4—C5—C10	−179.5 (3)	C18—C13—C14—C15	1.5 (4)
C4—C5—C6—C7	−2.8 (4)	S1—C13—C14—C15	175.7 (2)
C10—C5—C6—C7	177.9 (2)	C13—C14—C15—C16	−1.2 (4)
C4—C5—C6—C11	179.0 (3)	C14—C15—C16—C17	0.6 (4)
C10—C5—C6—C11	−0.3 (4)	C14—C15—C16—Br1	179.5 (2)
C5—C6—C7—O1	−177.7 (2)	C15—C16—C17—C18	−0.2 (4)
C11—C6—C7—O1	0.5 (4)	Br1—C16—C17—C18	−179.2 (2)
C5—C6—C7—C2	3.2 (4)	C16—C17—C18—C13	0.5 (5)
C11—C6—C7—C2	−178.6 (3)	C14—C13—C18—C17	−1.1 (4)
C8—O1—C7—C6	−179.4 (2)	S1—C13—C18—C17	−175.3 (2)

Cg1 and Cg2 are centroids of the C2–C7 benzene ring and the C13–C18 bromophenyl ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.95	2.58	3.397 (3)	144
C10—H10B···Cg1ii	0.98	2.87	3.604 (3)	132
C12—H12B···Cg2iii	0.98	2.84	3.671 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are centroids of the C2–C7 benzene ring and the C13–C18 bromo­phenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.95	2.58	3.397 (3)	144
C10—H10B⋯Cg1ii	0.98	2.87	3.604 (3)	132
C12—H12B⋯Cg2iii	0.98	2.84	3.671 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) .