3-(2-Bromo-phenyl-sulfon-yl)-5-cyclo-hexyl-2-methyl-1-benzo-furan.

In the title compound, C21H21BrO3S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo-furan and 2-bromo-phenyl fragments is 82.47 (5)°. In the crystal, mol-ecules related by inversion are paired into dimers via C-H⋯π and π-π inter-actions, the latter are indicated by the short distance of 3.607 (3) Å between the centroids of the furan rings. Inter-molecular C-H⋯O hydrogen bonds and short Br⋯O [3.280 (1) Å] contacts further consolidate the crystal packing.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C21H21BrO3S

M = 433.35

Monoclinic,

a = 7.3548 (1) Å

b = 20.4554 (4) Å

c = 12.6801 (2) Å

β = 92.463 (1)°

V = 1905.90 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.28 mm−1

T = 173 K

0.46 × 0.35 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.507, T max = 0.746

19277 measured reflections

4748 independent reflections

4028 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.03

4748 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.56 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003547/cv5444sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003547/cv5444Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003547/cv5444Isup3.cml

CCDC reference: 987378

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H21BrO3S	F(000) = 888
Mr = 433.35	Dx = 1.510 Mg m−3
Monoclinic, P21/n	Melting point = 445–446 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.3548 (1) Å	Cell parameters from 7682 reflections
b = 20.4554 (4) Å	θ = 2.6–28.2°
c = 12.6801 (2) Å	µ = 2.28 mm−1
β = 92.463 (1)°	T = 173 K
V = 1905.90 (5) Å3	Block, colourless
Z = 4	0.46 × 0.35 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	4748 independent reflections
Radiation source: rotating anode	4028 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −27→21
Tmin = 0.507, Tmax = 0.746	l = −16→16
19277 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F2) = 0.083	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0428P)2 + 1.0558P] where P = (Fo2 + 2Fc2)/3
4748 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.56 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	0.86740 (3)	0.705237 (11)	0.155454 (16)	0.02977 (8)
S1	0.43880 (6)	0.64983 (2)	0.08850 (3)	0.01954 (10)
O1	0.75164 (19)	0.49455 (7)	0.08436 (13)	0.0321 (3)
O2	0.24696 (18)	0.63578 (7)	0.08776 (11)	0.0263 (3)
O3	0.5080 (2)	0.68541 (7)	0.00109 (11)	0.0277 (3)
C1	0.5550 (3)	0.57650 (9)	0.10478 (15)	0.0216 (4)
C2	0.5104 (3)	0.52574 (9)	0.17993 (15)	0.0226 (4)
C3	0.3820 (3)	0.51623 (9)	0.25675 (15)	0.0238 (4)
H3	0.2955	0.5493	0.2706	0.029*
C4	0.3828 (3)	0.45752 (10)	0.31282 (16)	0.0277 (4)
C5	0.5130 (3)	0.40942 (11)	0.2906 (2)	0.0370 (5)
H5	0.5123	0.3694	0.3287	0.044*
C6	0.6409 (3)	0.41813 (10)	0.2159 (2)	0.0374 (5)
H6	0.7278	0.3853	0.2018	0.045*
C7	0.6369 (3)	0.47670 (10)	0.16263 (17)	0.0283 (4)
C8	0.6990 (3)	0.55528 (10)	0.05010 (17)	0.0266 (4)
C9	0.2428 (3)	0.44470 (10)	0.39452 (17)	0.0315 (5)
H9	0.1781	0.4869	0.4066	0.038*
C10	0.3273 (4)	0.42243 (13)	0.50155 (19)	0.0449 (7)
H10A	0.3927	0.3806	0.4924	0.054*
H10B	0.4167	0.4554	0.5279	0.054*
C11	0.1817 (4)	0.41342 (13)	0.5820 (2)	0.0480 (7)
H11A	0.2389	0.3973	0.6492	0.058*
H11B	0.1242	0.4561	0.5960	0.058*
C12	0.0365 (4)	0.36519 (13)	0.5428 (2)	0.0476 (7)
H12A	−0.0608	0.3631	0.5943	0.057*
H12B	0.0911	0.3211	0.5381	0.057*
C13	−0.0463 (3)	0.38442 (13)	0.4352 (2)	0.0418 (6)
H13A	−0.1179	0.4251	0.4422	0.050*
H13B	−0.1302	0.3495	0.4093	0.050*
C14	0.1001 (3)	0.39514 (12)	0.35539 (18)	0.0376 (5)
H14A	0.0423	0.4108	0.2881	0.045*
H14B	0.1606	0.3530	0.3414	0.045*
C15	0.8082 (3)	0.58153 (12)	−0.03582 (18)	0.0338 (5)
H15A	0.9024	0.5498	−0.0529	0.051*
H15B	0.8657	0.6226	−0.0129	0.051*
H15C	0.7287	0.5895	−0.0985	0.051*
C16	0.4887 (2)	0.69432 (8)	0.20708 (14)	0.0183 (4)
C17	0.3458 (3)	0.70484 (9)	0.27279 (16)	0.0247 (4)
H17	0.2291	0.6872	0.2547	0.030*
C18	0.3719 (3)	0.74109 (11)	0.36512 (17)	0.0309 (5)
H18	0.2732	0.7486	0.4095	0.037*
C19	0.5423 (3)	0.76600 (11)	0.39179 (17)	0.0294 (4)
H19	0.5603	0.7908	0.4547	0.035*
C20	0.6873 (3)	0.75516 (9)	0.32758 (16)	0.0238 (4)
H20	0.8044	0.7720	0.3468	0.029*
C21	0.6602 (2)	0.71964 (9)	0.23533 (15)	0.0199 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.01868 (11)	0.04310 (14)	0.02774 (12)	−0.00582 (8)	0.00347 (7)	−0.00653 (9)
S1	0.0179 (2)	0.0223 (2)	0.0181 (2)	0.00098 (17)	−0.00338 (16)	−0.00055 (17)
O1	0.0245 (7)	0.0260 (7)	0.0458 (9)	0.0041 (6)	0.0011 (6)	−0.0110 (7)
O2	0.0184 (6)	0.0298 (7)	0.0302 (7)	0.0002 (5)	−0.0059 (5)	−0.0027 (6)
O3	0.0303 (7)	0.0325 (7)	0.0201 (7)	0.0014 (6)	−0.0016 (5)	0.0038 (6)
C1	0.0216 (9)	0.0209 (9)	0.0220 (9)	0.0001 (7)	−0.0043 (7)	−0.0052 (7)
C2	0.0234 (9)	0.0187 (9)	0.0248 (9)	0.0003 (7)	−0.0081 (7)	−0.0037 (7)
C3	0.0265 (10)	0.0192 (9)	0.0252 (9)	0.0020 (7)	−0.0057 (7)	−0.0022 (8)
C4	0.0329 (11)	0.0216 (9)	0.0275 (10)	−0.0027 (8)	−0.0095 (8)	0.0005 (8)
C5	0.0410 (13)	0.0195 (10)	0.0493 (14)	0.0003 (9)	−0.0127 (11)	0.0044 (10)
C6	0.0340 (12)	0.0202 (10)	0.0568 (15)	0.0068 (9)	−0.0104 (10)	−0.0058 (10)
C7	0.0235 (10)	0.0226 (10)	0.0382 (12)	0.0012 (8)	−0.0054 (8)	−0.0080 (9)
C8	0.0219 (9)	0.0268 (10)	0.0306 (10)	−0.0007 (8)	−0.0030 (8)	−0.0100 (8)
C9	0.0426 (12)	0.0226 (10)	0.0285 (10)	−0.0037 (9)	−0.0075 (9)	0.0061 (8)
C10	0.0571 (16)	0.0402 (13)	0.0355 (13)	−0.0230 (12)	−0.0200 (11)	0.0145 (11)
C11	0.0709 (18)	0.0395 (14)	0.0323 (12)	−0.0198 (13)	−0.0125 (12)	0.0155 (11)
C12	0.0569 (16)	0.0409 (14)	0.0441 (14)	−0.0172 (12)	−0.0077 (12)	0.0185 (12)
C13	0.0422 (13)	0.0407 (13)	0.0417 (13)	−0.0104 (11)	−0.0076 (10)	0.0078 (11)
C14	0.0373 (12)	0.0395 (13)	0.0350 (12)	−0.0069 (10)	−0.0093 (10)	−0.0001 (10)
C15	0.0268 (10)	0.0424 (13)	0.0327 (11)	−0.0029 (9)	0.0062 (8)	−0.0138 (10)
C16	0.0193 (9)	0.0164 (8)	0.0189 (8)	0.0017 (7)	−0.0020 (7)	0.0006 (7)
C17	0.0196 (9)	0.0269 (10)	0.0277 (10)	−0.0004 (7)	0.0019 (7)	−0.0016 (8)
C18	0.0290 (11)	0.0335 (11)	0.0307 (11)	0.0017 (9)	0.0071 (8)	−0.0079 (9)
C19	0.0351 (11)	0.0274 (10)	0.0258 (10)	−0.0004 (9)	0.0019 (8)	−0.0082 (8)
C20	0.0236 (9)	0.0207 (9)	0.0267 (9)	−0.0021 (7)	−0.0041 (7)	−0.0013 (8)
C21	0.0192 (9)	0.0188 (9)	0.0217 (9)	0.0012 (7)	0.0005 (7)	0.0019 (7)

Br1—C21	1.8887 (19)	C10—H10B	0.9900
Br1—O2i	3.2793 (14)	C11—C12	1.521 (3)
S1—O3	1.4372 (15)	C11—H11A	0.9900
S1—O2	1.4395 (14)	C11—H11B	0.9900
S1—C1	1.7342 (19)	C12—C13	1.522 (3)
S1—C16	1.7823 (19)	C12—H12A	0.9900
O1—C8	1.367 (3)	C12—H12B	0.9900
O1—C7	1.379 (3)	C13—C14	1.525 (3)
C1—C8	1.361 (3)	C13—H13A	0.9900
C1—C2	1.456 (3)	C13—H13B	0.9900
C2—C7	1.392 (3)	C14—H14A	0.9900
C2—C3	1.399 (3)	C14—H14B	0.9900
C3—C4	1.395 (3)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.410 (3)	C15—H15C	0.9800
C4—C9	1.515 (3)	C16—C17	1.386 (3)
C5—C6	1.374 (4)	C16—C21	1.396 (3)
C5—H5	0.9500	C17—C18	1.392 (3)
C6—C7	1.375 (3)	C17—H17	0.9500
C6—H6	0.9500	C18—C19	1.381 (3)
C8—C15	1.482 (3)	C18—H18	0.9500
C9—C14	1.527 (3)	C19—C20	1.387 (3)
C9—C10	1.537 (3)	C19—H19	0.9500
C9—H9	1.0000	C20—C21	1.384 (3)
C10—C11	1.522 (4)	C20—H20	0.9500
C10—H10A	0.9900
C21—Br1—O2i	157.43 (6)	C10—C11—H11A	109.4
O3—S1—O2	118.40 (8)	C12—C11—H11B	109.4
O3—S1—C1	109.92 (9)	C10—C11—H11B	109.4
O2—S1—C1	107.81 (9)	H11A—C11—H11B	108.0
O3—S1—C16	108.97 (9)	C11—C12—C13	111.9 (2)
O2—S1—C16	105.89 (9)	C11—C12—H12A	109.2
C1—S1—C16	104.99 (8)	C13—C12—H12A	109.2
C8—O1—C7	107.19 (16)	C11—C12—H12B	109.2
C8—C1—C2	107.91 (17)	C13—C12—H12B	109.2
C8—C1—S1	127.25 (16)	H12A—C12—H12B	107.9
C2—C1—S1	124.83 (15)	C12—C13—C14	111.4 (2)
C7—C2—C3	119.02 (18)	C12—C13—H13A	109.3
C7—C2—C1	103.90 (18)	C14—C13—H13A	109.3
C3—C2—C1	137.08 (18)	C12—C13—H13B	109.3
C4—C3—C2	119.10 (18)	C14—C13—H13B	109.3
C4—C3—H3	120.5	H13A—C13—H13B	108.0
C2—C3—H3	120.5	C13—C14—C9	112.0 (2)
C3—C4—C5	119.1 (2)	C13—C14—H14A	109.2
C3—C4—C9	120.63 (19)	C9—C14—H14A	109.2
C5—C4—C9	120.23 (19)	C13—C14—H14B	109.2
C6—C5—C4	122.5 (2)	C9—C14—H14B	109.2
C6—C5—H5	118.7	H14A—C14—H14B	107.9
C4—C5—H5	118.7	C8—C15—H15A	109.5
C5—C6—C7	116.8 (2)	C8—C15—H15B	109.5
C5—C6—H6	121.6	H15A—C15—H15B	109.5
C7—C6—H6	121.6	C8—C15—H15C	109.5
C6—C7—O1	125.7 (2)	H15A—C15—H15C	109.5
C6—C7—C2	123.4 (2)	H15B—C15—H15C	109.5
O1—C7—C2	110.87 (18)	C17—C16—C21	119.25 (17)
C1—C8—O1	110.13 (18)	C17—C16—S1	116.89 (14)
C1—C8—C15	135.8 (2)	C21—C16—S1	123.85 (15)
O1—C8—C15	114.07 (18)	C16—C17—C18	120.49 (18)
C4—C9—C14	111.76 (18)	C16—C17—H17	119.8
C4—C9—C10	113.20 (19)	C18—C17—H17	119.8
C14—C9—C10	109.66 (18)	C19—C18—C17	119.56 (19)
C4—C9—H9	107.3	C19—C18—H18	120.2
C14—C9—H9	107.3	C17—C18—H18	120.2
C10—C9—H9	107.3	C18—C19—C20	120.64 (19)
C11—C10—C9	111.0 (2)	C18—C19—H19	119.7
C11—C10—H10A	109.4	C20—C19—H19	119.7
C9—C10—H10A	109.4	C21—C20—C19	119.59 (18)
C11—C10—H10B	109.4	C21—C20—H20	120.2
C9—C10—H10B	109.4	C19—C20—H20	120.2
H10A—C10—H10B	108.0	C20—C21—C16	120.47 (18)
C12—C11—C10	111.3 (2)	C20—C21—Br1	116.43 (14)
C12—C11—H11A	109.4	C16—C21—Br1	123.06 (14)
O3—S1—C1—C8	4.1 (2)	C3—C4—C9—C14	106.7 (2)
O2—S1—C1—C8	134.53 (17)	C5—C4—C9—C14	−71.7 (2)
C16—S1—C1—C8	−112.91 (18)	C3—C4—C9—C10	−128.9 (2)
O3—S1—C1—C2	−174.52 (15)	C5—C4—C9—C10	52.7 (3)
O2—S1—C1—C2	−44.14 (17)	C4—C9—C10—C11	177.3 (2)
C16—S1—C1—C2	68.42 (17)	C14—C9—C10—C11	−57.2 (3)
C8—C1—C2—C7	−0.1 (2)	C9—C10—C11—C12	56.7 (3)
S1—C1—C2—C7	178.84 (14)	C10—C11—C12—C13	−54.5 (3)
C8—C1—C2—C3	−179.6 (2)	C11—C12—C13—C14	53.1 (3)
S1—C1—C2—C3	−0.7 (3)	C12—C13—C14—C9	−54.6 (3)
C7—C2—C3—C4	−0.9 (3)	C4—C9—C14—C13	−177.32 (19)
C1—C2—C3—C4	178.6 (2)	C10—C9—C14—C13	56.3 (3)
C2—C3—C4—C5	0.0 (3)	O3—S1—C16—C17	129.89 (15)
C2—C3—C4—C9	−178.36 (17)	O2—S1—C16—C17	1.52 (17)
C3—C4—C5—C6	0.4 (3)	C1—S1—C16—C17	−112.40 (15)
C9—C4—C5—C6	178.8 (2)	O3—S1—C16—C21	−48.82 (18)
C4—C5—C6—C7	0.0 (3)	O2—S1—C16—C21	−177.19 (15)
C5—C6—C7—O1	−179.2 (2)	C1—S1—C16—C21	68.89 (17)
C5—C6—C7—C2	−0.9 (3)	C21—C16—C17—C18	1.0 (3)
C8—O1—C7—C6	178.2 (2)	S1—C16—C17—C18	−177.78 (16)
C8—O1—C7—C2	−0.4 (2)	C16—C17—C18—C19	−0.8 (3)
C3—C2—C7—C6	1.3 (3)	C17—C18—C19—C20	−0.1 (3)
C1—C2—C7—C6	−178.32 (19)	C18—C19—C20—C21	0.7 (3)
C3—C2—C7—O1	179.89 (16)	C19—C20—C21—C16	−0.5 (3)
C1—C2—C7—O1	0.3 (2)	C19—C20—C21—Br1	−178.13 (15)
C2—C1—C8—O1	−0.2 (2)	C17—C16—C21—C20	−0.4 (3)
S1—C1—C8—O1	−179.02 (13)	S1—C16—C21—C20	178.32 (14)
C2—C1—C8—C15	179.3 (2)	C17—C16—C21—Br1	177.12 (14)
S1—C1—C8—C15	0.5 (3)	S1—C16—C21—Br1	−4.2 (2)
C7—O1—C8—C1	0.3 (2)	O2i—Br1—C21—C20	80.7 (2)
C7—O1—C8—C15	−179.30 (17)	O2i—Br1—C21—C16	−96.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ii	0.95	2.61	3.487 (2)	155
C20—H20···O3ii	0.95	2.56	3.382 (2)	144
C15—H15C···Cg1iii	0.98	2.69	3.531 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2i	0.95	2.61	3.487 (2)	155
C20—H20⋯O3i	0.95	2.56	3.382 (2)	144
C15—H15C⋯Cg1ii	0.98	2.69	3.531 (2)	144

Symmetry codes: (i) ; (ii) .