3-(4-Bromo-phenyl-sulfon-yl)-5-cyclo-hexyl-2-methyl-1-benzofuran.

In the title compound, C(21)H(21)BrO(3)S, the cyclo-hexyl ring adopts a chair conformation. The 4-bromo-phenyl ring makes a dihedral angle of 80.88 (6)° with the mean plane of the benzofuran fragment. An intra-molecular C-H⋯O hydrogen bond is formed between an O atom of the sulfonyl group and one H atom of the aromatic ring such that a five-membered ring is formed. The crystal packing is stabilized by an inter-molecular C-H⋯O hydrogen bond, which links the mol-ecules into chains with graph-set notation C(6) running parallel to the c axis, and π-π stacking inter-actions [centroid-centroid distance = 3.6129 (12) Å].

Related literature

For the biological 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. (2011 ▶); Seo et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H21BrO3S

M = 433.35

Monoclinic,

a = 16.8264 (3) Å

b = 8.7627 (1) Å

c = 13.3545 (2) Å

β = 104.248 (1)°

V = 1908.48 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.28 mm−1

T = 173 K

0.31 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.543, T max = 0.686

18100 measured reflections

4739 independent reflections

3566 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.03

4739 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.71 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 PLATON (Spek,2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001791/bx2395sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001791/bx2395Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001791/bx2395Isup3.cml

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

C21H21BrO3S	F(000) = 888
Mr = 433.35	Dx = 1.508 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5934 reflections
a = 16.8264 (3) Å	θ = 2.6–27.2°
b = 8.7627 (1) Å	µ = 2.28 mm−1
c = 13.3545 (2) Å	T = 173 K
β = 104.248 (1)°	Block, colourless
V = 1908.48 (5) Å3	0.31 × 0.19 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4739 independent reflections
Radiation source: rotating anode	3566 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.3°
φ and ω scans	h = −18→22
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→7
Tmin = 0.543, Tmax = 0.686	l = −17→17
18100 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0533P)2 + 0.5992P] where P = (Fo2 + 2Fc2)/3
4739 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.71 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	0.472627 (17)	0.39062 (4)	0.30549 (2)	0.05789 (12)
S1	0.15069 (3)	0.28324 (5)	0.47083 (4)	0.02514 (12)
O1	0.04011 (9)	0.67903 (17)	0.41683 (12)	0.0338 (4)
O2	0.09589 (10)	0.18906 (17)	0.39712 (12)	0.0352 (4)
O3	0.17627 (9)	0.23523 (16)	0.57671 (11)	0.0311 (3)
C1	0.11029 (12)	0.4652 (2)	0.46944 (15)	0.0250 (4)
C2	0.13778 (12)	0.5779 (2)	0.54926 (16)	0.0250 (4)
C3	0.19440 (13)	0.5830 (2)	0.64531 (17)	0.0263 (4)
H3	0.2256	0.4951	0.6720	0.032*
C4	0.20449 (12)	0.7184 (2)	0.70136 (17)	0.0288 (5)
C5	0.15718 (14)	0.8459 (2)	0.6599 (2)	0.0368 (5)
H5	0.1644	0.9381	0.6985	0.044*
C6	0.10060 (14)	0.8430 (2)	0.5654 (2)	0.0378 (5)
H6	0.0691	0.9304	0.5385	0.045*
C7	0.09228 (13)	0.7077 (2)	0.51260 (17)	0.0302 (5)
C8	0.05259 (12)	0.5303 (2)	0.39189 (17)	0.0299 (5)
C9	0.26505 (13)	0.7263 (2)	0.80598 (17)	0.0308 (5)
H9	0.2646	0.8333	0.8320	0.037*
C10	0.35212 (14)	0.6904 (3)	0.79958 (18)	0.0404 (6)
H10A	0.3693	0.7654	0.7536	0.049*
H10B	0.3534	0.5878	0.7690	0.049*
C11	0.41288 (16)	0.6951 (3)	0.9066 (2)	0.0471 (6)
H11A	0.4680	0.6648	0.8998	0.057*
H11B	0.4166	0.8008	0.9335	0.057*
C12	0.38692 (19)	0.5901 (3)	0.9823 (2)	0.0506 (7)
H12A	0.4252	0.6013	1.0512	0.061*
H12B	0.3895	0.4830	0.9597	0.061*
C13	0.30039 (19)	0.6264 (4)	0.9898 (2)	0.0544 (7)
H13A	0.2994	0.7293	1.0200	0.065*
H13B	0.2835	0.5519	1.0362	0.065*
C14	0.23995 (16)	0.6211 (3)	0.88381 (19)	0.0438 (6)
H14A	0.1849	0.6511	0.8910	0.053*
H14B	0.2363	0.5151	0.8574	0.053*
C15	0.00326 (14)	0.4780 (3)	0.29081 (17)	0.0382 (5)
H15A	0.0170	0.3717	0.2798	0.057*
H15B	0.0151	0.5421	0.2361	0.057*
H15C	−0.0551	0.4855	0.2894	0.057*
C16	0.24026 (13)	0.3119 (2)	0.42616 (15)	0.0249 (4)
C17	0.23543 (13)	0.3041 (2)	0.32088 (15)	0.0282 (4)
H17	0.1846	0.2815	0.2737	0.034*
C18	0.30421 (15)	0.3291 (3)	0.28488 (17)	0.0338 (5)
H18	0.3012	0.3253	0.2130	0.041*
C19	0.37760 (14)	0.3597 (3)	0.35501 (19)	0.0336 (5)
C20	0.38350 (14)	0.3691 (3)	0.45991 (18)	0.0355 (5)
H20	0.4346	0.3913	0.5067	0.043*
C21	0.31415 (13)	0.3457 (3)	0.49569 (16)	0.0305 (5)
H21	0.3170	0.3527	0.5675	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.03863 (18)	0.0885 (3)	0.0517 (2)	0.00045 (13)	0.02099 (14)	−0.00445 (14)
S1	0.0269 (3)	0.0250 (2)	0.0201 (2)	−0.0028 (2)	−0.0007 (2)	0.00023 (19)
O1	0.0247 (8)	0.0351 (8)	0.0382 (9)	0.0053 (6)	0.0014 (7)	0.0107 (7)
O2	0.0351 (9)	0.0351 (8)	0.0300 (8)	−0.0102 (7)	−0.0024 (7)	−0.0058 (7)
O3	0.0376 (8)	0.0300 (7)	0.0230 (8)	−0.0007 (6)	0.0019 (7)	0.0045 (6)
C1	0.0236 (10)	0.0275 (10)	0.0227 (10)	0.0008 (8)	0.0034 (8)	0.0042 (8)
C2	0.0218 (10)	0.0235 (9)	0.0308 (11)	0.0016 (7)	0.0087 (9)	0.0036 (8)
C3	0.0246 (11)	0.0238 (9)	0.0296 (11)	0.0018 (8)	0.0049 (9)	0.0003 (8)
C4	0.0234 (10)	0.0266 (10)	0.0379 (12)	−0.0027 (8)	0.0105 (9)	−0.0040 (9)
C5	0.0319 (12)	0.0247 (10)	0.0546 (15)	0.0010 (9)	0.0123 (12)	−0.0066 (10)
C6	0.0288 (12)	0.0266 (11)	0.0576 (16)	0.0083 (9)	0.0096 (12)	0.0052 (11)
C7	0.0211 (10)	0.0313 (11)	0.0377 (12)	0.0027 (8)	0.0065 (9)	0.0084 (9)
C8	0.0223 (10)	0.0365 (11)	0.0307 (11)	0.0000 (9)	0.0063 (9)	0.0084 (9)
C9	0.0303 (11)	0.0265 (10)	0.0347 (12)	−0.0040 (9)	0.0064 (10)	−0.0096 (9)
C10	0.0258 (12)	0.0608 (16)	0.0346 (13)	−0.0044 (11)	0.0075 (10)	−0.0037 (11)
C11	0.0308 (13)	0.0652 (18)	0.0415 (15)	−0.0023 (12)	0.0018 (11)	−0.0119 (13)
C12	0.0581 (18)	0.0480 (15)	0.0381 (15)	0.0051 (13)	−0.0026 (13)	−0.0055 (12)
C13	0.064 (2)	0.0674 (18)	0.0335 (14)	−0.0088 (15)	0.0159 (14)	−0.0057 (12)
C14	0.0414 (14)	0.0578 (16)	0.0359 (14)	−0.0108 (11)	0.0168 (12)	−0.0085 (11)
C15	0.0276 (11)	0.0559 (15)	0.0262 (11)	−0.0029 (11)	−0.0026 (9)	0.0109 (11)
C16	0.0267 (10)	0.0228 (9)	0.0228 (10)	0.0016 (8)	0.0013 (8)	−0.0004 (8)
C17	0.0287 (11)	0.0316 (11)	0.0191 (10)	0.0009 (9)	−0.0041 (9)	−0.0041 (8)
C18	0.0415 (13)	0.0364 (11)	0.0228 (11)	0.0034 (10)	0.0064 (10)	−0.0033 (9)
C19	0.0289 (12)	0.0365 (11)	0.0363 (13)	0.0022 (9)	0.0095 (10)	−0.0014 (10)
C20	0.0270 (12)	0.0450 (13)	0.0300 (12)	0.0003 (10)	−0.0018 (10)	−0.0028 (10)
C21	0.0314 (12)	0.0366 (11)	0.0195 (10)	0.0009 (9)	−0.0015 (9)	−0.0001 (9)

Br1—C19	1.894 (2)	C10—H10B	0.9900
S1—O2	1.4330 (15)	C11—C12	1.509 (4)
S1—O3	1.4360 (15)	C11—H11A	0.9900
S1—C1	1.731 (2)	C11—H11B	0.9900
S1—C16	1.770 (2)	C12—C13	1.517 (4)
O1—C8	1.374 (3)	C12—H12A	0.9900
O1—C7	1.385 (3)	C12—H12B	0.9900
C1—C8	1.359 (3)	C13—C14	1.526 (4)
C1—C2	1.444 (3)	C13—H13A	0.9900
C2—C7	1.391 (3)	C13—H13B	0.9900
C2—C3	1.398 (3)	C14—H14A	0.9900
C3—C4	1.391 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.405 (3)	C15—H15B	0.9800
C4—C9	1.515 (3)	C15—H15C	0.9800
C5—C6	1.381 (3)	C16—C21	1.388 (3)
C5—H5	0.9500	C16—C17	1.390 (3)
C6—C7	1.369 (3)	C17—C18	1.376 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.473 (3)	C18—C19	1.380 (3)
C9—C10	1.521 (3)	C18—H18	0.9500
C9—C14	1.525 (3)	C19—C20	1.382 (3)
C9—H9	1.0000	C20—C21	1.381 (3)
C10—C11	1.540 (3)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
O2—S1—O3	119.59 (9)	C12—C11—H11B	109.3
O2—S1—C1	109.78 (10)	C10—C11—H11B	109.3
O3—S1—C1	107.58 (9)	H11A—C11—H11B	107.9
O2—S1—C16	107.91 (10)	C11—C12—C13	110.9 (2)
O3—S1—C16	107.43 (9)	C11—C12—H12A	109.5
C1—S1—C16	103.33 (9)	C13—C12—H12A	109.5
C8—O1—C7	107.22 (15)	C11—C12—H12B	109.5
C8—C1—C2	108.29 (18)	C13—C12—H12B	109.5
C8—C1—S1	126.89 (17)	H12A—C12—H12B	108.0
C2—C1—S1	124.67 (15)	C12—C13—C14	111.3 (2)
C7—C2—C3	119.29 (19)	C12—C13—H13A	109.4
C7—C2—C1	104.56 (18)	C14—C13—H13A	109.4
C3—C2—C1	136.16 (18)	C12—C13—H13B	109.4
C4—C3—C2	119.09 (19)	C14—C13—H13B	109.4
C4—C3—H3	120.5	H13A—C13—H13B	108.0
C2—C3—H3	120.5	C13—C14—C9	112.3 (2)
C3—C4—C5	119.0 (2)	C13—C14—H14A	109.1
C3—C4—C9	120.07 (18)	C9—C14—H14A	109.1
C5—C4—C9	120.93 (19)	C13—C14—H14B	109.1
C6—C5—C4	122.8 (2)	C9—C14—H14B	109.1
C6—C5—H5	118.6	H14A—C14—H14B	107.9
C4—C5—H5	118.6	C8—C15—H15A	109.5
C7—C6—C5	116.5 (2)	C8—C15—H15B	109.5
C7—C6—H6	121.7	H15A—C15—H15B	109.5
C5—C6—H6	121.7	C8—C15—H15C	109.5
C6—C7—O1	126.46 (19)	H15A—C15—H15C	109.5
C6—C7—C2	123.3 (2)	H15B—C15—H15C	109.5
O1—C7—C2	110.23 (18)	C21—C16—C17	120.5 (2)
C1—C8—O1	109.70 (18)	C21—C16—S1	120.10 (16)
C1—C8—C15	134.7 (2)	C17—C16—S1	119.43 (16)
O1—C8—C15	115.61 (18)	C18—C17—C16	120.06 (19)
C4—C9—C10	112.16 (18)	C18—C17—H17	120.0
C4—C9—C14	111.38 (18)	C16—C17—H17	120.0
C10—C9—C14	110.2 (2)	C17—C18—C19	118.9 (2)
C4—C9—H9	107.6	C17—C18—H18	120.6
C10—C9—H9	107.6	C19—C18—H18	120.6
C14—C9—H9	107.6	C18—C19—C20	121.9 (2)
C9—C10—C11	111.8 (2)	C18—C19—Br1	118.82 (18)
C9—C10—H10A	109.3	C20—C19—Br1	119.28 (18)
C11—C10—H10A	109.3	C21—C20—C19	119.1 (2)
C9—C10—H10B	109.3	C21—C20—H20	120.5
C11—C10—H10B	109.3	C19—C20—H20	120.5
H10A—C10—H10B	107.9	C20—C21—C16	119.6 (2)
C12—C11—C10	111.7 (2)	C20—C21—H21	120.2
C12—C11—H11A	109.3	C16—C21—H21	120.2
C10—C11—H11A	109.3
O2—S1—C1—C8	−21.0 (2)	C7—O1—C8—C15	−178.98 (18)
O3—S1—C1—C8	−152.62 (18)	C3—C4—C9—C10	59.7 (3)
C16—S1—C1—C8	93.9 (2)	C5—C4—C9—C10	−121.0 (2)
O2—S1—C1—C2	164.01 (17)	C3—C4—C9—C14	−64.3 (3)
O3—S1—C1—C2	32.4 (2)	C5—C4—C9—C14	115.0 (2)
C16—S1—C1—C2	−81.09 (18)	C4—C9—C10—C11	−178.6 (2)
C8—C1—C2—C7	0.4 (2)	C14—C9—C10—C11	−53.9 (3)
S1—C1—C2—C7	176.20 (16)	C9—C10—C11—C12	55.4 (3)
C8—C1—C2—C3	−179.7 (2)	C10—C11—C12—C13	−55.3 (3)
S1—C1—C2—C3	−3.9 (4)	C11—C12—C13—C14	55.3 (3)
C7—C2—C3—C4	−0.7 (3)	C12—C13—C14—C9	−55.6 (3)
C1—C2—C3—C4	179.4 (2)	C4—C9—C14—C13	179.6 (2)
C2—C3—C4—C5	0.3 (3)	C10—C9—C14—C13	54.5 (3)
C2—C3—C4—C9	179.58 (18)	O2—S1—C16—C21	−155.16 (16)
C3—C4—C5—C6	0.1 (3)	O3—S1—C16—C21	−24.96 (19)
C9—C4—C5—C6	−179.2 (2)	C1—S1—C16—C21	88.60 (18)
C4—C5—C6—C7	0.0 (4)	O2—S1—C16—C17	26.52 (19)
C5—C6—C7—O1	−179.5 (2)	O3—S1—C16—C17	156.72 (16)
C5—C6—C7—C2	−0.5 (3)	C1—S1—C16—C17	−89.71 (17)
C8—O1—C7—C6	178.8 (2)	C21—C16—C17—C18	0.4 (3)
C8—O1—C7—C2	−0.3 (2)	S1—C16—C17—C18	178.71 (16)
C3—C2—C7—C6	0.9 (3)	C16—C17—C18—C19	0.8 (3)
C1—C2—C7—C6	−179.2 (2)	C17—C18—C19—C20	−1.4 (3)
C3—C2—C7—O1	−179.99 (18)	C17—C18—C19—Br1	178.92 (16)
C1—C2—C7—O1	−0.1 (2)	C18—C19—C20—C21	0.6 (3)
C2—C1—C8—O1	−0.6 (2)	Br1—C19—C20—C21	−179.67 (17)
S1—C1—C8—O1	−176.28 (15)	C19—C20—C21—C16	0.6 (3)
C2—C1—C8—C15	178.8 (2)	C17—C16—C21—C20	−1.2 (3)
S1—C1—C8—C15	3.1 (4)	S1—C16—C21—C20	−179.45 (17)
C7—O1—C8—C1	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.40	3.125 (3)	131
C18—H18···O3i	0.95	2.48	3.120 (3)	125

Ring 1	Ring 2	φ	d	Δ
O1/C7/C2/C1/C8	(O1/C7/C2/C1/C8)ii	0.0	3.6129 (12)	0.938

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2	0.98	2.40	3.125 (3)	131
C18—H18⋯O3i	0.95	2.48	3.120 (3)	125

Symmetry code: (i) .