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

In the title compound, C(20)H(19)BrO(3)S, the cyclo-pentyl ring adopts an envelope conformation. The 4-bromo-phenyl ring makes a dihedral angle of 82.09 (6)° with the mean plane [mean deviation = 0.026 (2) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds and Br⋯O contacts [3.309 (2) Å].

Related literature

For background information and the crystal structure of a related compound, see: Seo et al. (2011 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C20H19BrO3S

M = 419.32

Monoclinic,

a = 6.8956 (2) Å

b = 17.1034 (3) Å

c = 15.7773 (3) Å

β = 97.533 (1)°

V = 1844.69 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.36 mm−1

T = 173 K

0.38 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.469, T max = 0.570

18310 measured reflections

4602 independent reflections

3416 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.02

4602 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.73 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 datablock(s) global, I. DOI: 10.1107/S1600536812019411/fy2055sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019411/fy2055Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019411/fy2055Isup3.cml

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

C20H19BrO3S	F(000) = 856
Mr = 419.32	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5006 reflections
a = 6.8956 (2) Å	θ = 2.4–26.9°
b = 17.1034 (3) Å	µ = 2.36 mm−1
c = 15.7773 (3) Å	T = 173 K
β = 97.533 (1)°	Block, colourless
V = 1844.69 (7) Å3	0.38 × 0.34 × 0.27 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4602 independent reflections
Radiation source: rotating anode	3416 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→22
Tmin = 0.469, Tmax = 0.570	l = −21→19
18310 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) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.8231P] where P = (Fo2 + 2Fc2)/3
4602 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.73 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	−0.32092 (5)	0.301064 (16)	0.016006 (19)	0.06550 (13)
S1	0.31357 (7)	0.28508 (3)	0.34905 (3)	0.02688 (12)
O1	0.2226 (2)	0.48448 (8)	0.45861 (10)	0.0398 (4)
O2	0.5019 (2)	0.27163 (8)	0.32240 (10)	0.0356 (3)
O3	0.2418 (2)	0.23232 (8)	0.40858 (9)	0.0363 (3)
C1	0.3124 (3)	0.37925 (11)	0.38922 (12)	0.0282 (4)
C2	0.4174 (3)	0.44557 (11)	0.36055 (13)	0.0288 (4)
C3	0.5464 (3)	0.45853 (11)	0.30148 (13)	0.0313 (4)
H3	0.5924	0.4161	0.2707	0.038*
C4	0.6077 (3)	0.53476 (12)	0.28803 (14)	0.0351 (5)
C5	0.5410 (4)	0.59592 (12)	0.33602 (15)	0.0406 (5)
H5	0.5841	0.6476	0.3268	0.049*
C6	0.4158 (4)	0.58411 (12)	0.39592 (15)	0.0408 (5)
H6	0.3735	0.6259	0.4286	0.049*
C7	0.3554 (3)	0.50843 (12)	0.40580 (14)	0.0338 (5)
C8	0.1965 (3)	0.40590 (12)	0.44621 (14)	0.0351 (5)
C9	0.0490 (4)	0.36946 (14)	0.49391 (18)	0.0509 (7)
H9A	−0.0824	0.3813	0.4652	0.076*
H9B	0.0634	0.3903	0.5523	0.076*
H9C	0.0685	0.3127	0.4959	0.076*
C10	0.7396 (4)	0.55251 (12)	0.22173 (16)	0.0426 (6)
H10	0.7525	0.6106	0.2187	0.051*
C11	0.6704 (5)	0.52353 (19)	0.13200 (18)	0.0642 (8)
H11A	0.5648	0.5574	0.1037	0.077*
H11B	0.6206	0.4693	0.1334	0.077*
C12	0.8493 (6)	0.52695 (18)	0.0848 (2)	0.0763 (11)
H12A	0.8563	0.4797	0.0491	0.092*
H12B	0.8435	0.5736	0.0474	0.092*
C13	1.0259 (6)	0.53131 (18)	0.1533 (3)	0.0822 (12)
H13A	1.0902	0.5830	0.1525	0.099*
H13B	1.1222	0.4902	0.1443	0.099*
C14	0.9451 (4)	0.5187 (2)	0.2377 (2)	0.0685 (9)
H14A	0.9416	0.4623	0.2519	0.082*
H14B	1.0253	0.5465	0.2850	0.082*
C15	0.1402 (3)	0.28833 (10)	0.25667 (12)	0.0257 (4)
C16	−0.0527 (3)	0.26893 (12)	0.26253 (14)	0.0339 (5)
H16	−0.0905	0.2530	0.3157	0.041*
C17	−0.1896 (3)	0.27292 (13)	0.19020 (15)	0.0402 (5)
H17	−0.3224	0.2596	0.1931	0.048*
C18	−0.1312 (3)	0.29636 (12)	0.11402 (15)	0.0377 (5)
C19	0.0603 (4)	0.31567 (12)	0.10699 (14)	0.0382 (5)
H19	0.0971	0.3315	0.0536	0.046*
C20	0.1983 (3)	0.31153 (11)	0.17929 (13)	0.0318 (4)
H20	0.3311	0.3244	0.1760	0.038*

	U11	U22	U33	U12	U13	U23
Br1	0.0750 (2)	0.04795 (17)	0.0610 (2)	0.00540 (13)	−0.03790 (16)	−0.00334 (12)
S1	0.0311 (3)	0.0203 (2)	0.0284 (2)	0.00110 (17)	0.00070 (19)	−0.00012 (18)
O1	0.0528 (10)	0.0260 (7)	0.0438 (9)	−0.0022 (6)	0.0187 (8)	−0.0062 (6)
O2	0.0312 (8)	0.0323 (7)	0.0424 (9)	0.0064 (6)	0.0021 (7)	−0.0042 (6)
O3	0.0500 (10)	0.0247 (7)	0.0336 (8)	−0.0015 (6)	0.0034 (7)	0.0042 (6)
C1	0.0340 (11)	0.0227 (9)	0.0277 (10)	−0.0017 (8)	0.0030 (8)	−0.0015 (8)
C2	0.0317 (11)	0.0228 (9)	0.0306 (10)	−0.0021 (7)	−0.0001 (8)	−0.0017 (7)
C3	0.0334 (12)	0.0258 (10)	0.0349 (11)	−0.0007 (8)	0.0050 (9)	−0.0013 (8)
C4	0.0371 (13)	0.0282 (10)	0.0402 (12)	−0.0016 (8)	0.0057 (9)	0.0031 (9)
C5	0.0473 (14)	0.0229 (10)	0.0526 (14)	−0.0043 (9)	0.0098 (11)	−0.0004 (9)
C6	0.0527 (15)	0.0246 (10)	0.0466 (13)	−0.0029 (9)	0.0114 (11)	−0.0071 (9)
C7	0.0382 (13)	0.0291 (10)	0.0346 (11)	−0.0018 (8)	0.0068 (9)	−0.0031 (8)
C8	0.0435 (13)	0.0246 (10)	0.0377 (12)	−0.0023 (8)	0.0072 (9)	−0.0026 (8)
C9	0.0638 (18)	0.0349 (12)	0.0610 (16)	−0.0046 (11)	0.0349 (14)	−0.0037 (11)
C10	0.0514 (15)	0.0244 (10)	0.0551 (15)	−0.0008 (9)	0.0188 (12)	0.0070 (10)
C11	0.076 (2)	0.0694 (19)	0.0507 (17)	−0.0048 (15)	0.0195 (15)	0.0125 (14)
C12	0.113 (3)	0.0466 (16)	0.082 (2)	0.0057 (17)	0.061 (2)	0.0127 (15)
C13	0.075 (2)	0.0528 (18)	0.132 (3)	−0.0021 (16)	0.065 (3)	0.0032 (19)
C14	0.0474 (18)	0.072 (2)	0.088 (2)	−0.0004 (14)	0.0185 (16)	0.0145 (17)
C15	0.0281 (11)	0.0196 (8)	0.0291 (10)	0.0022 (7)	0.0027 (8)	−0.0020 (7)
C16	0.0303 (12)	0.0347 (11)	0.0378 (12)	−0.0025 (8)	0.0083 (9)	−0.0032 (9)
C17	0.0283 (12)	0.0408 (12)	0.0502 (14)	−0.0009 (9)	0.0006 (10)	−0.0085 (10)
C18	0.0420 (14)	0.0276 (10)	0.0389 (12)	0.0057 (8)	−0.0117 (10)	−0.0069 (9)
C19	0.0542 (15)	0.0315 (11)	0.0279 (11)	−0.0023 (9)	0.0014 (10)	0.0011 (8)
C20	0.0332 (12)	0.0295 (10)	0.0329 (11)	−0.0035 (8)	0.0041 (9)	−0.0007 (8)

Br1—C18	1.892 (2)	C10—C11	1.517 (4)
Br1—O3i	3.3090 (16)	C10—C14	1.521 (4)
S1—O2	1.4348 (15)	C10—H10	1.0000
S1—O3	1.4362 (15)	C11—C12	1.523 (4)
S1—C1	1.7313 (19)	C11—H11A	0.9900
S1—C15	1.760 (2)	C11—H11B	0.9900
O1—C8	1.367 (2)	C12—C13	1.520 (5)
O1—C7	1.379 (3)	C12—H12A	0.9900
C1—C8	1.358 (3)	C12—H12B	0.9900
C1—C2	1.449 (3)	C13—C14	1.525 (4)
C2—C3	1.388 (3)	C13—H13A	0.9900
C2—C7	1.388 (3)	C13—H13B	0.9900
C3—C4	1.395 (3)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.404 (3)	C15—C16	1.386 (3)
C4—C10	1.504 (3)	C15—C20	1.392 (3)
C5—C6	1.376 (3)	C16—C17	1.384 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.375 (3)	C17—C18	1.377 (3)
C6—H6	0.9500	C17—H17	0.9500
C8—C9	1.480 (3)	C18—C19	1.380 (4)
C9—H9A	0.9800	C19—C20	1.388 (3)
C9—H9B	0.9800	C19—H19	0.9500
C9—H9C	0.9800	C20—H20	0.9500
C18—Br1—O3i	153.82 (8)	C14—C10—H10	107.4
O2—S1—O3	119.56 (9)	C10—C11—C12	105.5 (3)
O2—S1—C1	107.71 (9)	C10—C11—H11A	110.6
O3—S1—C1	109.06 (9)	C12—C11—H11A	110.6
O2—S1—C15	107.74 (9)	C10—C11—H11B	110.6
O3—S1—C15	107.85 (9)	C12—C11—H11B	110.6
C1—S1—C15	103.80 (9)	H11A—C11—H11B	108.8
C8—O1—C7	106.92 (16)	C13—C12—C11	106.2 (3)
C8—C1—C2	107.78 (17)	C13—C12—H12A	110.5
C8—C1—S1	125.88 (16)	C11—C12—H12A	110.5
C2—C1—S1	125.97 (15)	C13—C12—H12B	110.5
C3—C2—C7	119.27 (18)	C11—C12—H12B	110.5
C3—C2—C1	136.45 (18)	H12A—C12—H12B	108.7
C7—C2—C1	104.23 (18)	C12—C13—C14	105.3 (3)
C2—C3—C4	119.00 (19)	C12—C13—H13A	110.7
C2—C3—H3	120.5	C14—C13—H13A	110.7
C4—C3—H3	120.5	C12—C13—H13B	110.7
C3—C4—C5	119.2 (2)	C14—C13—H13B	110.7
C3—C4—C10	121.13 (19)	H13A—C13—H13B	108.8
C5—C4—C10	119.70 (18)	C10—C14—C13	103.9 (3)
C6—C5—C4	122.7 (2)	C10—C14—H14A	111.0
C6—C5—H5	118.6	C13—C14—H14A	111.0
C4—C5—H5	118.6	C10—C14—H14B	111.0
C7—C6—C5	116.3 (2)	C13—C14—H14B	111.0
C7—C6—H6	121.9	H14A—C14—H14B	109.0
C5—C6—H6	121.9	C16—C15—C20	121.06 (19)
C6—C7—O1	125.68 (19)	C16—C15—S1	119.38 (16)
C6—C7—C2	123.5 (2)	C20—C15—S1	119.55 (15)
O1—C7—C2	110.74 (17)	C17—C16—C15	119.4 (2)
C1—C8—O1	110.30 (18)	C17—C16—H16	120.3
C1—C8—C9	134.34 (19)	C15—C16—H16	120.3
O1—C8—C9	115.33 (18)	C18—C17—C16	119.2 (2)
C8—C9—H9A	109.5	C18—C17—H17	120.4
C8—C9—H9B	109.5	C16—C17—H17	120.4
H9A—C9—H9B	109.5	C17—C18—C19	122.2 (2)
C8—C9—H9C	109.5	C17—C18—Br1	118.42 (18)
H9A—C9—H9C	109.5	C19—C18—Br1	119.40 (18)
H9B—C9—H9C	109.5	C18—C19—C20	118.8 (2)
C4—C10—C11	116.0 (2)	C18—C19—H19	120.6
C4—C10—C14	116.3 (2)	C20—C19—H19	120.6
C11—C10—C14	101.7 (2)	C19—C20—C15	119.4 (2)
C4—C10—H10	107.4	C19—C20—H20	120.3
C11—C10—H10	107.4	C15—C20—H20	120.3
O2—S1—C1—C8	−155.71 (19)	C7—O1—C8—C9	−176.6 (2)
O3—S1—C1—C8	−24.5 (2)	C3—C4—C10—C11	53.8 (3)
C15—S1—C1—C8	90.2 (2)	C5—C4—C10—C11	−124.7 (3)
O2—S1—C1—C2	32.2 (2)	C3—C4—C10—C14	−65.7 (3)
O3—S1—C1—C2	163.33 (17)	C5—C4—C10—C14	115.8 (3)
C15—S1—C1—C2	−81.9 (2)	C4—C10—C11—C12	−164.0 (2)
C8—C1—C2—C3	−176.0 (2)	C14—C10—C11—C12	−36.8 (3)
S1—C1—C2—C3	−2.7 (4)	C10—C11—C12—C13	18.2 (3)
C8—C1—C2—C7	1.1 (2)	C11—C12—C13—C14	7.8 (3)
S1—C1—C2—C7	174.40 (16)	C4—C10—C14—C13	168.5 (2)
C7—C2—C3—C4	−1.2 (3)	C11—C10—C14—C13	41.6 (3)
C1—C2—C3—C4	175.6 (2)	C12—C13—C14—C10	−30.8 (3)
C2—C3—C4—C5	1.5 (3)	O2—S1—C15—C16	153.86 (15)
C2—C3—C4—C10	−177.0 (2)	O3—S1—C15—C16	23.52 (18)
C3—C4—C5—C6	−0.4 (4)	C1—S1—C15—C16	−92.10 (17)
C10—C4—C5—C6	178.1 (2)	O2—S1—C15—C20	−27.16 (18)
C4—C5—C6—C7	−1.0 (4)	O3—S1—C15—C20	−157.50 (15)
C5—C6—C7—O1	−176.3 (2)	C1—S1—C15—C20	86.88 (17)
C5—C6—C7—C2	1.4 (4)	C20—C15—C16—C17	−0.2 (3)
C8—O1—C7—C6	177.0 (2)	S1—C15—C16—C17	178.79 (16)
C8—O1—C7—C2	−1.0 (2)	C15—C16—C17—C18	−0.2 (3)
C3—C2—C7—C6	−0.4 (3)	C16—C17—C18—C19	0.4 (3)
C1—C2—C7—C6	−178.1 (2)	C16—C17—C18—Br1	179.82 (16)
C3—C2—C7—O1	177.66 (19)	O3i—Br1—C18—C17	−10.6 (3)
C1—C2—C7—O1	−0.1 (2)	O3i—Br1—C18—C19	168.84 (12)
C2—C1—C8—O1	−1.8 (3)	C17—C18—C19—C20	−0.2 (3)
S1—C1—C8—O1	−175.07 (15)	Br1—C18—C19—C20	−179.62 (15)
C2—C1—C8—C9	176.1 (3)	C18—C19—C20—C15	−0.2 (3)
S1—C1—C8—C9	2.8 (4)	C16—C15—C20—C19	0.4 (3)
C7—O1—C8—C1	1.7 (2)	S1—C15—C20—C19	−178.60 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ii	0.95	2.51	3.169 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2i	0.95	2.51	3.169 (3)	126

Symmetry code: (i) .