5-Bromo-2,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

In the title compound, C(11)H(11)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by non-classical inter-molecular C-H⋯O hydrogen bonding, and by inter-molecular C-Br⋯π inter-actions, with C-Br⋯Cg = 3.629 Å (Cg is the centroid of the benzene ring). In addition, the crystal structure exhibits aromatic π-π interactions between the furan rings of neighbouring molecules [centroid-centroid distance = 4.206 (6) Å].

Related literature

For the crystal structures of similar 5-halo-2-methyl-3-methyl­sulfinyl-1-benzofuran derivatives. see: Choi et al. (2007 ▶). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ▶); von Reuss & König (2004 ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶).

Experimental

Crystal data

C11H11BrO2S

M = 287.17

Monoclinic,

a = 16.929 (2) Å

b = 5.1001 (6) Å

c = 13.800 (2) Å

β = 106.962 (2)°

V = 1139.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.77 mm−1

T = 173 K

0.60 × 0.30 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.211, T max = 0.602

3270 measured reflections

1832 independent reflections

1760 reflections with I > 2σ(I)

R int = 0.111

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.06

1832 reflections

138 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.31 e Å−3

Δρmin = −0.82 e Å−3

Absolute structure: Flack (1983 ▶), 582 Friedel pairs

Flack parameter: −0.003 (12)

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/S1600536809034011/hg2560sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034011/hg2560Isup2.hkl

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

C11H11BrO2S	F(000) = 576
Mr = 287.17	Dx = 1.674 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2606 reflections
a = 16.929 (2) Å	θ = 2.5–27.4°
b = 5.1001 (6) Å	µ = 3.77 mm−1
c = 13.800 (2) Å	T = 173 K
β = 106.962 (2)°	Block, colorless
V = 1139.7 (3) Å3	0.60 × 0.30 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	1832 independent reflections
Radiation source: fine-focus sealed tube	1760 reflections with I > 2σ(I)
graphite	Rint = 0.111
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.5°
φ and ω scans	h = −21→19
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −6→6
Tmin = 0.211, Tmax = 0.602	l = −13→17
3270 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.071P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1832 reflections	Δρmax = 1.31 e Å−3
138 parameters	Δρmin = −0.82 e Å−3
2 restraints	Absolute structure: Flack (1983), 582 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.003 (12)

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	0.80657 (3)	1.10273 (9)	0.53574 (4)	0.03592 (18)
S2	0.47258 (6)	0.4834 (2)	0.39045 (8)	0.0260 (3)
O1	0.60773 (18)	0.2770 (7)	0.6641 (2)	0.0234 (7)
C2	0.6253 (2)	0.5717 (8)	0.5481 (3)	0.0210 (9)
C1	0.5474 (2)	0.4374 (8)	0.5090 (3)	0.0196 (8)
C3	0.6679 (2)	0.7694 (9)	0.5131 (3)	0.0226 (8)
H3	0.6470	0.8467	0.4497	0.027*
C9	0.7699 (3)	0.4064 (11)	0.8116 (4)	0.0362 (13)
H9A	0.7768	0.2220	0.8027	0.043*
H9B	0.7326	0.4324	0.8514	0.043*
H9C	0.8225	0.4832	0.8457	0.043*
C8	0.5396 (2)	0.2678 (9)	0.5812 (3)	0.0222 (9)
C6	0.7356 (3)	0.5336 (10)	0.7103 (3)	0.0253 (9)
C4	0.7437 (3)	0.8416 (9)	0.5800 (4)	0.0261 (9)
C7	0.6596 (2)	0.4648 (9)	0.6435 (3)	0.0215 (8)
C5	0.7778 (3)	0.7289 (10)	0.6741 (4)	0.0283 (10)
H5	0.8294	0.7837	0.7139	0.034*
O2	0.4684 (2)	0.7724 (8)	0.3685 (3)	0.0389 (10)
C10	0.4738 (3)	0.0806 (9)	0.5865 (4)	0.0279 (10)
H10A	0.4286	0.0927	0.5255	0.042*
H10B	0.4548	0.1227	0.6437	0.042*
H10C	0.4955	−0.0946	0.5937	0.042*
C11	0.5294 (4)	0.3399 (11)	0.3125 (4)	0.0361 (12)
H11A	0.4998	0.3659	0.2425	0.054*
H11B	0.5362	0.1555	0.3264	0.054*
H11C	0.5827	0.4216	0.3271	0.054*

	U11	U22	U33	U12	U13	U23
Br	0.0297 (2)	0.0241 (2)	0.0578 (3)	−0.00886 (19)	0.01865 (19)	−0.0052 (3)
S2	0.0213 (5)	0.0276 (6)	0.0247 (5)	−0.0042 (4)	−0.0002 (4)	0.0032 (4)
O1	0.0239 (15)	0.0250 (17)	0.0218 (15)	−0.0003 (12)	0.0075 (12)	0.0008 (13)
C2	0.018 (2)	0.019 (2)	0.025 (2)	0.0008 (14)	0.0051 (16)	−0.0027 (16)
C1	0.0152 (17)	0.0208 (19)	0.0210 (19)	−0.0012 (14)	0.0024 (14)	0.0019 (16)
C3	0.0211 (19)	0.020 (2)	0.026 (2)	0.0005 (15)	0.0066 (16)	0.0004 (16)
C9	0.027 (2)	0.051 (4)	0.026 (3)	0.007 (2)	0.0003 (19)	−0.002 (2)
C8	0.0208 (18)	0.024 (2)	0.021 (2)	0.0003 (15)	0.0043 (16)	−0.0022 (16)
C6	0.0197 (19)	0.027 (2)	0.027 (2)	0.0039 (16)	0.0047 (16)	−0.0055 (19)
C4	0.0216 (19)	0.0183 (19)	0.040 (3)	−0.0028 (15)	0.0121 (17)	−0.0054 (19)
C7	0.0190 (18)	0.021 (2)	0.025 (2)	0.0022 (15)	0.0071 (15)	−0.0030 (18)
C5	0.0176 (18)	0.034 (3)	0.032 (2)	−0.0017 (16)	0.0051 (16)	−0.012 (2)
O2	0.041 (2)	0.0286 (19)	0.039 (2)	0.0081 (16)	−0.0001 (18)	0.0065 (16)
C10	0.027 (2)	0.023 (2)	0.035 (2)	−0.0066 (17)	0.0121 (19)	0.0006 (18)
C11	0.052 (3)	0.031 (3)	0.026 (2)	−0.007 (2)	0.012 (2)	−0.002 (2)

Br—C4	1.913 (5)	C9—H9B	0.9600
S2—O2	1.502 (4)	C9—H9C	0.9600
S2—C1	1.769 (4)	C8—C10	1.486 (6)
S2—C11	1.795 (7)	C6—C7	1.391 (6)
O1—C8	1.368 (5)	C6—C5	1.400 (8)
O1—C7	1.384 (6)	C4—C5	1.383 (8)
C2—C7	1.387 (6)	C5—H5	0.9300
C2—C3	1.404 (7)	C10—H10A	0.9600
C2—C1	1.444 (5)	C10—H10B	0.9600
C1—C8	1.354 (7)	C10—H10C	0.9600
C3—C4	1.394 (6)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C9—C6	1.496 (7)	C11—H11C	0.9600
C9—H9A	0.9600
O2—S2—C1	107.2 (2)	C7—C6—C9	122.8 (5)
O2—S2—C11	106.4 (3)	C5—C6—C9	122.9 (4)
C1—S2—C11	97.8 (2)	C5—C4—C3	124.3 (5)
C8—O1—C7	106.4 (3)	C5—C4—Br	118.1 (3)
C7—C2—C3	119.6 (4)	C3—C4—Br	117.6 (4)
C7—C2—C1	104.6 (4)	O1—C7—C2	110.6 (3)
C3—C2—C1	135.8 (4)	O1—C7—C6	123.9 (4)
C8—C1—C2	107.6 (4)	C2—C7—C6	125.5 (5)
C8—C1—S2	124.6 (3)	C4—C5—C6	121.0 (4)
C2—C1—S2	127.7 (4)	C4—C5—H5	119.5
C4—C3—C2	115.3 (4)	C6—C5—H5	119.5
C4—C3—H3	122.4	C8—C10—H10A	109.5
C2—C3—H3	122.4	C8—C10—H10B	109.5
C6—C9—H9A	109.5	H10A—C10—H10B	109.5
C6—C9—H9B	109.5	C8—C10—H10C	109.5
H9A—C9—H9B	109.5	H10A—C10—H10C	109.5
C6—C9—H9C	109.5	H10B—C10—H10C	109.5
H9A—C9—H9C	109.5	S2—C11—H11A	109.5
H9B—C9—H9C	109.5	S2—C11—H11B	109.5
C1—C8—O1	110.8 (4)	H11A—C11—H11B	109.5
C1—C8—C10	133.0 (4)	S2—C11—H11C	109.5
O1—C8—C10	116.2 (4)	H11A—C11—H11C	109.5
C7—C6—C5	114.3 (4)	H11B—C11—H11C	109.5
C7—C2—C1—C8	0.8 (5)	C2—C3—C4—C5	1.1 (7)
C3—C2—C1—C8	−178.2 (5)	C2—C3—C4—Br	178.2 (3)
C7—C2—C1—S2	179.5 (3)	C8—O1—C7—C2	−0.7 (5)
C3—C2—C1—S2	0.6 (8)	C8—O1—C7—C6	179.5 (4)
O2—S2—C1—C8	139.5 (4)	C3—C2—C7—O1	179.1 (4)
C11—S2—C1—C8	−110.6 (5)	C1—C2—C7—O1	−0.1 (5)
O2—S2—C1—C2	−39.0 (5)	C3—C2—C7—C6	−1.0 (7)
C11—S2—C1—C2	70.8 (5)	C1—C2—C7—C6	179.8 (4)
C7—C2—C3—C4	0.3 (7)	C5—C6—C7—O1	−179.8 (4)
C1—C2—C3—C4	179.1 (5)	C9—C6—C7—O1	1.1 (7)
C2—C1—C8—O1	−1.3 (5)	C5—C6—C7—C2	0.4 (7)
S2—C1—C8—O1	179.9 (3)	C9—C6—C7—C2	−178.7 (5)
C2—C1—C8—C10	179.1 (5)	C3—C4—C5—C6	−1.9 (8)
S2—C1—C8—C10	0.3 (8)	Br—C4—C5—C6	−179.0 (4)
C7—O1—C8—C1	1.2 (5)	C7—C6—C5—C4	1.0 (7)
C7—O1—C8—C10	−179.0 (4)	C9—C6—C5—C4	−179.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2i	0.96	2.42	3.242 (7)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2i	0.96	2.42	3.242 (7)	143

Symmetry code: (i) .