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

In the title compound, C21H21BrO2S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.178 (2) Å] of the benzo-furan ring system and the mean plane of the 3-bromo-phenyl ring is 86.52 (6)°. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π hydrogen bonds, and by a slipped π-π inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.518 (3) Å, inter-planar distance = 3.471 (3) Å and slippage = 0.573 (3) Å], resulting in a three-dimensional network.

Related literature

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

Experimental

Crystal data

C21H21BrO2S

M = 417.35

Monoclinic,

a = 17.6432 (9) Å

b = 8.9425 (5) Å

c = 12.4776 (7) Å

β = 108.277 (3)°

V = 1869.33 (18) Å3

Z = 4

Mo Kα radiation

μ = 2.32 mm−1

T = 173 K

0.33 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.482, T max = 0.746

13952 measured reflections

3290 independent reflections

2635 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.02

3290 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 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/S160053681400316X/gk2602sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400316X/gk2602Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400316X/gk2602Isup3.cml

CCDC reference: 986408

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

C21H21BrO2S	F(000) = 856
Mr = 417.35	Dx = 1.483 Mg m−3
Monoclinic, P21/c	Melting point = 415–416 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.6432 (9) Å	Cell parameters from 5628 reflections
b = 8.9425 (5) Å	θ = 2.4–27.9°
c = 12.4776 (7) Å	µ = 2.32 mm−1
β = 108.277 (3)°	T = 173 K
V = 1869.33 (18) Å3	Block, colourless
Z = 4	0.33 × 0.25 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	3290 independent reflections
Radiation source: rotating anode	2635 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.035
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.4°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→10
Tmin = 0.482, Tmax = 0.746	l = −14→14
13952 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) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0334P)2 + 1.1209P] where P = (Fo2 + 2Fc2)/3
3290 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.35 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	0.957798 (17)	0.38271 (5)	0.67946 (3)	0.07366 (16)
S1	0.63694 (3)	0.26562 (6)	0.46130 (5)	0.03447 (16)
O1	0.53393 (8)	0.66112 (17)	0.40386 (12)	0.0319 (4)
O2	0.64909 (10)	0.19977 (18)	0.57522 (14)	0.0427 (4)
C1	0.60397 (12)	0.4510 (2)	0.46411 (18)	0.0282 (5)
C2	0.63088 (12)	0.5613 (2)	0.55301 (17)	0.0256 (5)
C3	0.68650 (12)	0.5662 (2)	0.66079 (18)	0.0273 (5)
H3	0.7173	0.4802	0.6915	0.033*
C4	0.69659 (12)	0.6982 (2)	0.72299 (18)	0.0280 (5)
C5	0.64951 (13)	0.8227 (3)	0.67603 (19)	0.0319 (5)
H5	0.6567	0.9126	0.7186	0.038*
C6	0.59308 (13)	0.8197 (3)	0.57033 (19)	0.0336 (5)
H6	0.5612	0.9046	0.5399	0.040*
C7	0.58539 (12)	0.6878 (2)	0.51138 (18)	0.0274 (5)
C8	0.54640 (12)	0.5152 (3)	0.37802 (18)	0.0296 (5)
C9	0.75683 (13)	0.7056 (3)	0.84023 (18)	0.0316 (5)
H9	0.7543	0.8085	0.8704	0.038*
C10	0.73622 (14)	0.5948 (3)	0.92025 (19)	0.0380 (6)
H10A	0.6824	0.6180	0.9245	0.046*
H10B	0.7348	0.4924	0.8895	0.046*
C11	0.79601 (17)	0.5999 (3)	1.0382 (2)	0.0499 (7)
H11A	0.7937	0.6990	1.0723	0.060*
H11B	0.7820	0.5231	1.0860	0.060*
C12	0.87977 (16)	0.5719 (3)	1.0348 (2)	0.0515 (7)
H12A	0.8834	0.4687	1.0081	0.062*
H12B	0.9179	0.5810	1.1120	0.062*
C13	0.90249 (16)	0.6819 (4)	0.9573 (2)	0.0512 (7)
H13A	0.9560	0.6560	0.9528	0.061*
H13B	0.9054	0.7839	0.9892	0.061*
C14	0.84220 (14)	0.6799 (3)	0.8393 (2)	0.0433 (6)
H14A	0.8451	0.5822	0.8035	0.052*
H14B	0.8564	0.7586	0.7931	0.052*
C15	0.49706 (14)	0.4623 (3)	0.26513 (19)	0.0373 (6)
H15A	0.5103	0.3578	0.2551	0.056*
H15B	0.5078	0.5241	0.2067	0.056*
H15C	0.4404	0.4699	0.2589	0.056*
C16	0.73449 (14)	0.3121 (2)	0.45342 (18)	0.0319 (5)
C17	0.79756 (14)	0.3239 (3)	0.55204 (19)	0.0353 (5)
H17	0.7903	0.3067	0.6233	0.042*
C18	0.87176 (15)	0.3615 (3)	0.5440 (2)	0.0418 (6)
C19	0.88362 (16)	0.3840 (3)	0.4411 (2)	0.0451 (6)
H19	0.9350	0.4092	0.4373	0.054*
C20	0.81998 (17)	0.3694 (3)	0.3439 (2)	0.0446 (7)
H20	0.8278	0.3846	0.2727	0.054*
C21	0.74495 (16)	0.3330 (3)	0.34816 (19)	0.0378 (6)
H21	0.7013	0.3224	0.2808	0.045*

	U11	U22	U33	U12	U13	U23
Br1	0.03672 (18)	0.1296 (4)	0.0485 (2)	0.00172 (17)	0.00453 (14)	−0.02246 (18)
S1	0.0418 (3)	0.0248 (3)	0.0302 (3)	−0.0027 (2)	0.0018 (3)	−0.0026 (2)
O1	0.0302 (8)	0.0323 (10)	0.0295 (8)	0.0027 (7)	0.0040 (7)	0.0072 (7)
O2	0.0528 (10)	0.0314 (10)	0.0403 (10)	0.0006 (8)	0.0097 (8)	0.0081 (8)
C1	0.0291 (11)	0.0263 (13)	0.0268 (11)	−0.0029 (9)	0.0054 (9)	0.0020 (10)
C2	0.0262 (11)	0.0219 (12)	0.0287 (12)	−0.0036 (9)	0.0085 (9)	0.0008 (9)
C3	0.0277 (11)	0.0225 (12)	0.0288 (12)	0.0012 (9)	0.0046 (9)	0.0028 (9)
C4	0.0283 (11)	0.0252 (13)	0.0309 (12)	−0.0043 (9)	0.0099 (10)	−0.0016 (10)
C5	0.0370 (12)	0.0217 (12)	0.0380 (13)	0.0002 (10)	0.0132 (11)	−0.0040 (10)
C6	0.0335 (12)	0.0271 (13)	0.0392 (13)	0.0071 (10)	0.0100 (11)	0.0060 (11)
C7	0.0249 (11)	0.0282 (13)	0.0279 (11)	0.0000 (9)	0.0065 (9)	0.0047 (10)
C8	0.0288 (11)	0.0300 (13)	0.0289 (12)	−0.0053 (10)	0.0074 (10)	0.0030 (10)
C9	0.0367 (12)	0.0239 (13)	0.0297 (12)	−0.0019 (10)	0.0039 (10)	−0.0051 (10)
C10	0.0412 (14)	0.0461 (16)	0.0284 (12)	−0.0063 (11)	0.0133 (11)	−0.0051 (11)
C11	0.0648 (18)	0.0553 (19)	0.0289 (13)	−0.0076 (14)	0.0135 (13)	−0.0022 (12)
C12	0.0511 (16)	0.0556 (18)	0.0351 (14)	−0.0001 (13)	−0.0049 (13)	0.0036 (13)
C13	0.0372 (14)	0.0610 (19)	0.0454 (16)	−0.0093 (13)	−0.0016 (12)	0.0001 (14)
C14	0.0335 (13)	0.0559 (17)	0.0375 (14)	−0.0107 (12)	0.0067 (11)	0.0049 (12)
C15	0.0336 (12)	0.0450 (16)	0.0275 (12)	−0.0061 (11)	0.0012 (10)	0.0021 (11)
C16	0.0426 (13)	0.0197 (12)	0.0293 (12)	0.0048 (10)	0.0054 (10)	−0.0030 (9)
C17	0.0420 (14)	0.0350 (14)	0.0266 (12)	0.0079 (11)	0.0073 (11)	−0.0029 (10)
C18	0.0408 (14)	0.0444 (16)	0.0372 (14)	0.0054 (11)	0.0078 (11)	−0.0099 (12)
C19	0.0492 (15)	0.0421 (16)	0.0476 (16)	0.0020 (12)	0.0205 (13)	−0.0061 (12)
C20	0.0670 (18)	0.0348 (15)	0.0366 (14)	0.0071 (13)	0.0226 (14)	0.0012 (11)
C21	0.0556 (16)	0.0256 (13)	0.0267 (12)	0.0084 (11)	0.0050 (11)	−0.0009 (10)

Br1—C18	1.894 (2)	C11—C12	1.512 (4)
S1—O2	1.4907 (17)	C11—H11A	0.9900
S1—C1	1.761 (2)	C11—H11B	0.9900
S1—C16	1.803 (2)	C12—C13	1.519 (4)
O1—C8	1.378 (3)	C12—H12A	0.9900
O1—C7	1.385 (3)	C12—H12B	0.9900
C1—C8	1.353 (3)	C13—C14	1.522 (3)
C1—C2	1.449 (3)	C13—H13A	0.9900
C2—C7	1.390 (3)	C13—H13B	0.9900
C2—C3	1.395 (3)	C14—H14A	0.9900
C3—C4	1.393 (3)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.402 (3)	C15—H15B	0.9800
C4—C9	1.516 (3)	C15—H15C	0.9800
C5—C6	1.381 (3)	C16—C17	1.380 (3)
C5—H5	0.9500	C16—C21	1.395 (3)
C6—C7	1.374 (3)	C17—C18	1.386 (4)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.482 (3)	C18—C19	1.379 (4)
C9—C14	1.527 (3)	C19—C20	1.376 (4)
C9—C10	1.529 (3)	C19—H19	0.9500
C9—H9	1.0000	C20—C21	1.380 (4)
C10—C11	1.519 (3)	C20—H20	0.9500
C10—H10A	0.9900	C21—H21	0.9500
C10—H10B	0.9900
O2—S1—C1	107.61 (10)	C10—C11—H11B	109.5
O2—S1—C16	106.78 (10)	H11A—C11—H11B	108.1
C1—S1—C16	96.38 (10)	C11—C12—C13	111.5 (2)
C8—O1—C7	106.61 (16)	C11—C12—H12A	109.3
C8—C1—C2	107.62 (19)	C13—C12—H12A	109.3
C8—C1—S1	123.66 (17)	C11—C12—H12B	109.3
C2—C1—S1	128.71 (16)	C13—C12—H12B	109.3
C7—C2—C3	118.9 (2)	H12A—C12—H12B	108.0
C7—C2—C1	104.83 (18)	C12—C13—C14	111.4 (2)
C3—C2—C1	136.2 (2)	C12—C13—H13A	109.3
C4—C3—C2	119.5 (2)	C14—C13—H13A	109.3
C4—C3—H3	120.3	C12—C13—H13B	109.3
C2—C3—H3	120.3	C14—C13—H13B	109.3
C3—C4—C5	119.0 (2)	H13A—C13—H13B	108.0
C3—C4—C9	120.2 (2)	C13—C14—C9	112.5 (2)
C5—C4—C9	120.8 (2)	C13—C14—H14A	109.1
C6—C5—C4	122.6 (2)	C9—C14—H14A	109.1
C6—C5—H5	118.7	C13—C14—H14B	109.1
C4—C5—H5	118.7	C9—C14—H14B	109.1
C7—C6—C5	116.6 (2)	H14A—C14—H14B	107.8
C7—C6—H6	121.7	C8—C15—H15A	109.5
C5—C6—H6	121.7	C8—C15—H15B	109.5
C6—C7—O1	126.27 (19)	H15A—C15—H15B	109.5
C6—C7—C2	123.4 (2)	C8—C15—H15C	109.5
O1—C7—C2	110.36 (19)	H15A—C15—H15C	109.5
C1—C8—O1	110.57 (19)	H15B—C15—H15C	109.5
C1—C8—C15	133.6 (2)	C17—C16—C21	121.4 (2)
O1—C8—C15	115.83 (19)	C17—C16—S1	119.04 (18)
C4—C9—C14	112.37 (19)	C21—C16—S1	119.52 (18)
C4—C9—C10	111.31 (18)	C16—C17—C18	118.0 (2)
C14—C9—C10	110.16 (19)	C16—C17—H17	121.0
C4—C9—H9	107.6	C18—C17—H17	121.0
C14—C9—H9	107.6	C19—C18—C17	121.7 (2)
C10—C9—H9	107.6	C19—C18—Br1	120.2 (2)
C11—C10—C9	112.2 (2)	C17—C18—Br1	118.06 (19)
C11—C10—H10A	109.2	C20—C19—C18	119.1 (2)
C9—C10—H10A	109.2	C20—C19—H19	120.4
C11—C10—H10B	109.2	C18—C19—H19	120.4
C9—C10—H10B	109.2	C19—C20—C21	121.0 (2)
H10A—C10—H10B	107.9	C19—C20—H20	119.5
C12—C11—C10	110.8 (2)	C21—C20—H20	119.5
C12—C11—H11A	109.5	C20—C21—C16	118.7 (2)
C10—C11—H11A	109.5	C20—C21—H21	120.7
C12—C11—H11B	109.5	C16—C21—H21	120.7
O2—S1—C1—C8	−139.65 (19)	C7—O1—C8—C15	−179.84 (18)
C16—S1—C1—C8	110.4 (2)	C3—C4—C9—C14	62.5 (3)
O2—S1—C1—C2	40.6 (2)	C5—C4—C9—C14	−118.4 (2)
C16—S1—C1—C2	−69.3 (2)	C3—C4—C9—C10	−61.6 (3)
C8—C1—C2—C7	0.1 (2)	C5—C4—C9—C10	117.5 (2)
S1—C1—C2—C7	179.85 (17)	C4—C9—C10—C11	179.8 (2)
C8—C1—C2—C3	179.3 (2)	C14—C9—C10—C11	54.5 (3)
S1—C1—C2—C3	−0.9 (4)	C9—C10—C11—C12	−56.3 (3)
C7—C2—C3—C4	−1.6 (3)	C10—C11—C12—C13	56.0 (3)
C1—C2—C3—C4	179.3 (2)	C11—C12—C13—C14	−55.0 (3)
C2—C3—C4—C5	0.9 (3)	C12—C13—C14—C9	54.1 (3)
C2—C3—C4—C9	−179.93 (19)	C4—C9—C14—C13	−178.0 (2)
C3—C4—C5—C6	0.2 (3)	C10—C9—C14—C13	−53.3 (3)
C9—C4—C5—C6	−178.9 (2)	O2—S1—C16—C17	−18.3 (2)
C4—C5—C6—C7	−0.7 (3)	C1—S1—C16—C17	92.32 (19)
C5—C6—C7—O1	−178.7 (2)	O2—S1—C16—C21	160.74 (18)
C5—C6—C7—C2	0.0 (3)	C1—S1—C16—C21	−88.7 (2)
C8—O1—C7—C6	179.7 (2)	C21—C16—C17—C18	1.8 (3)
C8—O1—C7—C2	0.8 (2)	S1—C16—C17—C18	−179.20 (18)
C3—C2—C7—C6	1.1 (3)	C16—C17—C18—C19	−1.3 (4)
C1—C2—C7—C6	−179.5 (2)	C16—C17—C18—Br1	178.45 (18)
C3—C2—C7—O1	−179.96 (18)	C17—C18—C19—C20	0.3 (4)
C1—C2—C7—O1	−0.5 (2)	Br1—C18—C19—C20	−179.37 (19)
C2—C1—C8—O1	0.5 (2)	C18—C19—C20—C21	0.1 (4)
S1—C1—C8—O1	−179.36 (14)	C19—C20—C21—C16	0.4 (4)
C2—C1—C8—C15	179.3 (2)	C17—C16—C21—C20	−1.4 (3)
S1—C1—C8—C15	−0.5 (4)	S1—C16—C21—C20	179.61 (18)
C7—O1—C8—C1	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1i	0.98	2.58	3.358 (3)	136
C21—H21···O2ii	0.95	2.45	3.306 (3)	151
C15—H15C···Cg1iii	0.98	2.82	3.502 (3)	127

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
C15—H15A⋯O1i	0.98	2.58	3.358 (3)	136
C21—H21⋯O2ii	0.95	2.45	3.306 (3)	151
C15—H15C⋯Cg1iii	0.98	2.82	3.502 (3)	127

Symmetry codes: (i) ; (ii) ; (iii) .