5-Bromo-3-cyclo-hexyl-sulfonyl-2-methyl-1-benzofuran.

In the title compound, C(15)H(17)BrO(3)S, the cyclo-hexyl ring adopts a practically undistorted chair conformation [endocyclic torsion angles are within a 54.5-56.4 (3)° range] and the aryl-sulfonyl unit is positioned equatorial relative to the cyclo-hexyl group. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds and donor-acceptor Br⋯O contacts [3.250 (2) Å]. The crystal structure also exhibits aromatic π-π overlap between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.635 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 3-aryl­sulfonyl-5-bromo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C15H17BrO3S

M = 357.26

Triclinic,

a = 6.3452 (1) Å

b = 8.2065 (1) Å

c = 14.4866 (2) Å

α = 98.842 (1)°

β = 97.693 (1)°

γ = 96.385 (1)°

V = 731.95 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.95 mm−1

T = 173 K

0.33 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.585, T max = 0.746

13107 measured reflections

3377 independent reflections

3109 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.07

3377 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.70 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, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003515/ld2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003515/ld2001Isup2.hkl

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

C15H17BrO3S	Z = 2
Mr = 357.26	F(000) = 364
Triclinic, P1	Dx = 1.621 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3452 (1) Å	Cell parameters from 8112 reflections
b = 8.2065 (1) Å	θ = 2.7–27.5°
c = 14.4866 (2) Å	µ = 2.95 mm−1
α = 98.842 (1)°	T = 173 K
β = 97.693 (1)°	Block, colourless
γ = 96.385 (1)°	0.33 × 0.26 × 0.23 mm
V = 731.95 (2) Å3

Bruker SMART APEXII CCD diffractometer	3377 independent reflections
Radiation source: rotating anode	3109 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.4°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.585, Tmax = 0.746	l = −18→18
13107 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) = 0.073	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.2624P] where P = (Fo2 + 2Fc2)/3
3377 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.70 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	0.24178 (3)	0.58796 (3)	0.634104 (12)	0.03547 (8)
S1	0.21139 (7)	0.69361 (6)	0.22168 (3)	0.02801 (11)
O1	0.7467 (2)	0.92120 (16)	0.38017 (9)	0.0310 (3)
O2	0.2068 (3)	0.78049 (19)	0.14233 (10)	0.0400 (3)
O3	0.0254 (2)	0.6830 (2)	0.26875 (10)	0.0396 (3)
C1	0.4294 (3)	0.7824 (2)	0.30762 (12)	0.0267 (4)
C2	0.4500 (3)	0.7619 (2)	0.40566 (12)	0.0261 (3)
C3	0.3234 (3)	0.6829 (2)	0.46111 (12)	0.0284 (4)
H3	0.1862	0.6225	0.4355	0.034*
C4	0.4078 (3)	0.6967 (2)	0.55581 (13)	0.0286 (4)
C5	0.6076 (3)	0.7838 (3)	0.59542 (13)	0.0324 (4)
H5	0.6582	0.7887	0.6607	0.039*
C6	0.7337 (3)	0.8635 (3)	0.54056 (14)	0.0330 (4)
H6	0.8706	0.9243	0.5663	0.040*
C7	0.6495 (3)	0.8496 (2)	0.44644 (13)	0.0284 (4)
C8	0.6100 (3)	0.8776 (2)	0.29616 (13)	0.0290 (4)
C9	0.6862 (4)	0.9444 (3)	0.21558 (15)	0.0365 (4)
H9A	0.5693	0.9244	0.1619	0.055*
H9B	0.8070	0.8887	0.1974	0.055*
H9C	0.7330	1.0643	0.2340	0.055*
C10	0.2636 (3)	0.4859 (2)	0.18543 (12)	0.0244 (3)
H10	0.3071	0.4386	0.2436	0.029*
C11	0.4467 (3)	0.4811 (2)	0.12705 (13)	0.0288 (4)
H11A	0.5802	0.5433	0.1657	0.035*
H11B	0.4124	0.5353	0.0714	0.035*
C12	0.4807 (3)	0.3011 (3)	0.09420 (14)	0.0328 (4)
H12A	0.5919	0.2997	0.0523	0.039*
H12B	0.5334	0.2522	0.1498	0.039*
C13	0.2750 (3)	0.1955 (3)	0.04136 (16)	0.0419 (5)
H13A	0.2310	0.2363	−0.0182	0.050*
H13B	0.3015	0.0787	0.0249	0.050*
C14	0.0960 (4)	0.2023 (3)	0.10074 (18)	0.0474 (6)
H14A	0.1341	0.1512	0.1573	0.057*
H14B	−0.0373	0.1371	0.0636	0.057*
C15	0.0563 (3)	0.3812 (3)	0.13187 (14)	0.0358 (4)
H15A	−0.0560	0.3825	0.1732	0.043*
H15B	0.0050	0.4294	0.0757	0.043*

	U11	U22	U33	U12	U13	U23
Br1	0.03585 (12)	0.04254 (13)	0.02647 (11)	0.00000 (9)	0.00393 (8)	0.00562 (8)
S1	0.0262 (2)	0.0334 (2)	0.0240 (2)	0.00874 (18)	0.00065 (16)	0.00314 (18)
O1	0.0298 (7)	0.0289 (7)	0.0321 (7)	0.0000 (6)	0.0053 (5)	0.0004 (5)
O2	0.0471 (8)	0.0414 (8)	0.0332 (7)	0.0134 (7)	−0.0016 (6)	0.0129 (6)
O3	0.0277 (7)	0.0553 (10)	0.0352 (7)	0.0134 (7)	0.0045 (6)	0.0009 (7)
C1	0.0294 (9)	0.0247 (9)	0.0243 (8)	0.0049 (7)	0.0024 (7)	−0.0003 (7)
C2	0.0272 (8)	0.0236 (8)	0.0248 (8)	0.0043 (7)	0.0017 (6)	−0.0026 (7)
C3	0.0280 (9)	0.0290 (9)	0.0251 (8)	0.0023 (7)	0.0012 (7)	−0.0013 (7)
C4	0.0308 (9)	0.0270 (9)	0.0266 (8)	0.0035 (7)	0.0038 (7)	0.0007 (7)
C5	0.0348 (10)	0.0330 (10)	0.0255 (8)	0.0026 (8)	−0.0020 (7)	−0.0002 (7)
C6	0.0278 (9)	0.0323 (10)	0.0327 (10)	−0.0025 (8)	−0.0031 (7)	−0.0025 (8)
C7	0.0282 (9)	0.0256 (9)	0.0296 (9)	0.0029 (7)	0.0045 (7)	−0.0009 (7)
C8	0.0337 (9)	0.0242 (9)	0.0287 (9)	0.0076 (7)	0.0051 (7)	0.0000 (7)
C9	0.0413 (11)	0.0336 (10)	0.0379 (10)	0.0078 (9)	0.0114 (9)	0.0098 (8)
C10	0.0228 (8)	0.0285 (9)	0.0197 (7)	0.0003 (7)	0.0004 (6)	0.0023 (6)
C11	0.0243 (8)	0.0303 (9)	0.0312 (9)	0.0018 (7)	0.0057 (7)	0.0032 (7)
C12	0.0284 (9)	0.0316 (10)	0.0353 (10)	0.0052 (8)	0.0019 (7)	−0.0018 (8)
C13	0.0363 (11)	0.0423 (12)	0.0377 (11)	0.0002 (9)	−0.0012 (9)	−0.0124 (9)
C14	0.0374 (11)	0.0441 (13)	0.0496 (13)	−0.0147 (10)	0.0052 (10)	−0.0107 (10)
C15	0.0213 (8)	0.0485 (12)	0.0313 (9)	−0.0042 (8)	0.0018 (7)	−0.0047 (9)

Br1—O3i	3.250 (2)	C9—H9A	0.9800
Br1—C4	1.901 (2)	C9—H9B	0.9800
S1—O3	1.4409 (15)	C9—H9C	0.9800
S1—O2	1.4416 (15)	C10—C11	1.526 (2)
S1—C1	1.7408 (18)	C10—C15	1.530 (2)
S1—C10	1.7852 (18)	C10—H10	1.0000
O1—C8	1.370 (2)	C11—C12	1.529 (3)
O1—C7	1.378 (2)	C11—H11A	0.9900
C1—C8	1.357 (3)	C11—H11B	0.9900
C1—C2	1.446 (2)	C12—C13	1.523 (3)
C2—C3	1.388 (3)	C12—H12A	0.9900
C2—C7	1.392 (3)	C12—H12B	0.9900
C3—C4	1.387 (2)	C13—C14	1.515 (3)
C3—H3	0.9500	C13—H13A	0.9900
C4—C5	1.387 (3)	C13—H13B	0.9900
C5—C6	1.383 (3)	C14—C15	1.527 (3)
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.379 (3)	C14—H14B	0.9900
C6—H6	0.9500	C15—H15A	0.9900
C8—C9	1.479 (3)	C15—H15B	0.9900
C4—Br1—O3i	165.29 (6)	H9B—C9—H9C	109.5
O3—S1—O2	118.38 (9)	C11—C10—C15	112.06 (14)
O3—S1—C1	106.84 (9)	C11—C10—S1	111.82 (13)
O2—S1—C1	109.77 (9)	C15—C10—S1	108.98 (13)
O3—S1—C10	107.26 (9)	C11—C10—H10	107.9
O2—S1—C10	109.22 (9)	C15—C10—H10	107.9
C1—S1—C10	104.45 (8)	S1—C10—H10	107.9
C8—O1—C7	106.96 (14)	C10—C11—C12	110.24 (15)
C8—C1—C2	107.72 (16)	C10—C11—H11A	109.6
C8—C1—S1	127.65 (14)	C12—C11—H11A	109.6
C2—C1—S1	124.60 (14)	C10—C11—H11B	109.6
C3—C2—C7	119.65 (16)	C12—C11—H11B	109.6
C3—C2—C1	135.86 (17)	H11A—C11—H11B	108.1
C7—C2—C1	104.48 (16)	C13—C12—C11	111.97 (16)
C4—C3—C2	116.54 (17)	C13—C12—H12A	109.2
C4—C3—H3	121.7	C11—C12—H12A	109.2
C2—C3—H3	121.7	C13—C12—H12B	109.2
C3—C4—C5	123.20 (18)	C11—C12—H12B	109.2
C3—C4—Br1	118.01 (14)	H12A—C12—H12B	107.9
C5—C4—Br1	118.78 (14)	C14—C13—C12	111.09 (17)
C6—C5—C4	120.46 (17)	C14—C13—H13A	109.4
C6—C5—H5	119.8	C12—C13—H13A	109.4
C4—C5—H5	119.8	C14—C13—H13B	109.4
C7—C6—C5	116.23 (17)	C12—C13—H13B	109.4
C7—C6—H6	121.9	H13A—C13—H13B	108.0
C5—C6—H6	121.9	C13—C14—C15	111.34 (19)
O1—C7—C6	125.59 (17)	C13—C14—H14A	109.4
O1—C7—C2	110.49 (16)	C15—C14—H14A	109.4
C6—C7—C2	123.91 (18)	C13—C14—H14B	109.4
C1—C8—O1	110.33 (16)	C15—C14—H14B	109.4
C1—C8—C9	134.57 (18)	H14A—C14—H14B	108.0
O1—C8—C9	115.09 (17)	C14—C15—C10	110.09 (16)
C8—C9—H9A	109.5	C14—C15—H15A	109.6
C8—C9—H9B	109.5	C10—C15—H15A	109.6
H9A—C9—H9B	109.5	C14—C15—H15B	109.6
C8—C9—H9C	109.5	C10—C15—H15B	109.6
H9A—C9—H9C	109.5	H15A—C15—H15B	108.2
O3—S1—C1—C8	−150.39 (17)	C3—C2—C7—C6	0.4 (3)
O2—S1—C1—C8	−20.86 (19)	C1—C2—C7—C6	179.62 (18)
C10—S1—C1—C8	96.14 (18)	C2—C1—C8—O1	−0.3 (2)
O3—S1—C1—C2	31.47 (18)	S1—C1—C8—O1	−178.67 (13)
O2—S1—C1—C2	161.01 (15)	C2—C1—C8—C9	−179.0 (2)
C10—S1—C1—C2	−81.99 (16)	S1—C1—C8—C9	2.6 (3)
C8—C1—C2—C3	178.9 (2)	C7—O1—C8—C1	0.59 (19)
S1—C1—C2—C3	−2.7 (3)	C7—O1—C8—C9	179.58 (15)
C8—C1—C2—C7	−0.1 (2)	O3—S1—C10—C11	175.09 (12)
S1—C1—C2—C7	178.32 (13)	O2—S1—C10—C11	45.64 (14)
C7—C2—C3—C4	−0.3 (3)	C1—S1—C10—C11	−71.74 (14)
C1—C2—C3—C4	−179.25 (19)	O3—S1—C10—C15	50.66 (14)
C2—C3—C4—C5	−0.1 (3)	O2—S1—C10—C15	−78.79 (14)
C2—C3—C4—Br1	−179.16 (13)	C1—S1—C10—C15	163.83 (13)
C3—C4—C5—C6	0.4 (3)	C15—C10—C11—C12	−55.1 (2)
Br1—C4—C5—C6	179.53 (15)	S1—C10—C11—C12	−177.82 (12)
C4—C5—C6—C7	−0.4 (3)	C10—C11—C12—C13	54.5 (2)
C8—O1—C7—C6	−179.79 (18)	C11—C12—C13—C14	−55.5 (3)
C8—O1—C7—C2	−0.68 (19)	C12—C13—C14—C15	56.4 (3)
C5—C6—C7—O1	178.95 (17)	C13—C14—C15—C10	−56.4 (2)
C5—C6—C7—C2	0.0 (3)	C11—C10—C15—C14	56.2 (2)
C3—C2—C7—O1	−178.72 (15)	S1—C10—C15—C14	−179.50 (15)
C1—C2—C7—O1	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ii	0.95	2.57	3.518 (2)	174
C9—H9B···O3iii	0.98	2.55	3.303 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.57	3.518 (2)	174
C9—H9B⋯O3ii	0.98	2.55	3.303 (2)	134

Symmetry codes: (i) ; (ii) .