5-Bromo-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

In the title compound, C17H21BrO2S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfinyl unit is positioned equatorially relative to the cyclo-hexyl group. The benzo-furan unit is essentially planar, with an r.m.s. deviation of 0.016 (2) Å. In the crystal, mol-ecules are linked by weak C-H⋯O, C-H⋯π and Br⋯π [3.663 (2) Å] inter-actions, resulting in a three-dimensional network. A Br⋯Br [3.6838 (6) Å] contact is observed. The O atom of the sulfinyl group is disordered over two orientations with an occupancy ratio of 0.863 (5):0.137 (5).

Related literature

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

Experimental

Crystal data

C17H21BrO2S

M = 369.31

Triclinic,

a = 5.9051 (4) Å

b = 11.7060 (9) Å

c = 12.7906 (10) Å

α = 65.839 (4)°

β = 85.795 (4)°

γ = 83.394 (4)°

V = 801.01 (10) Å3

Z = 2

Mo Kα radiation

μ = 2.70 mm−1

T = 173 K

0.38 × 0.29 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.429, T max = 0.520

14547 measured reflections

3981 independent reflections

3419 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.091

S = 1.05

3981 reflections

203 parameters

4 restraints

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −0.88 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/S1600536814003171/gg2135sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003171/gg2135Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003171/gg2135Isup3.cml

CCDC reference: 986409

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

C17H21BrO2S	Z = 2
Mr = 369.31	F(000) = 380
Triclinic, P1	Dx = 1.531 Mg m−3
Hall symbol: -P 1	Melting point = 450–451 K
a = 5.9051 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7060 (9) Å	Cell parameters from 6652 reflections
c = 12.7906 (10) Å	θ = 3.1–28.4°
α = 65.839 (4)°	µ = 2.70 mm−1
β = 85.795 (4)°	T = 173 K
γ = 83.394 (4)°	Block, colourless
V = 801.01 (10) Å3	0.38 × 0.29 × 0.28 mm

Bruker SMART APEXII CCD diffractometer	3981 independent reflections
Radiation source: rotating anode	3419 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 28.5°, θmin = 3.1°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
Tmin = 0.429, Tmax = 0.520	l = −17→17
14547 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) = 0.091	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0292P)2 + 1.0109P] where P = (Fo2 + 2Fc2)/3
3981 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 1.28 e Å−3
4 restraints	Δρmin = −0.88 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	Occ. (<1)
Br1	−0.27560 (5)	0.86915 (3)	0.02612 (2)	0.03843 (10)
S1	0.58237 (11)	0.47281 (6)	0.18104 (6)	0.03238 (15)
O1	0.4834 (3)	0.69082 (15)	0.35369 (15)	0.0281 (4)
O2A	0.8063 (4)	0.4118 (2)	0.2215 (2)	0.0408 (6)	0.863 (5)
O2B	0.637 (2)	0.5186 (11)	0.0592 (3)	0.036 (3)	0.137 (5)
C1	0.4916 (4)	0.5828 (2)	0.2422 (2)	0.0231 (5)
C2	0.2955 (4)	0.6766 (2)	0.2109 (2)	0.0222 (4)
C3	0.1240 (4)	0.7157 (2)	0.1289 (2)	0.0232 (5)
C4	−0.0359 (4)	0.8119 (2)	0.1324 (2)	0.0264 (5)
C5	−0.0339 (4)	0.8713 (2)	0.2086 (2)	0.0290 (5)
C6	0.1401 (4)	0.8330 (2)	0.2854 (2)	0.0290 (5)
H6	0.1498	0.8709	0.3377	0.035*
C7	0.2994 (4)	0.7378 (2)	0.2837 (2)	0.0246 (5)
C8	0.5969 (4)	0.5962 (2)	0.3264 (2)	0.0273 (5)
C9	0.1167 (4)	0.6589 (2)	0.0433 (2)	0.0292 (5)
H9A	−0.0024	0.6006	0.0669	0.044*
H9B	0.2647	0.6131	0.0395	0.044*
H9C	0.0829	0.7257	−0.0323	0.044*
C10	−0.2122 (5)	0.9752 (2)	0.2065 (3)	0.0404 (7)
H10A	−0.1816	1.0035	0.2660	0.061*
H10B	−0.3633	0.9438	0.2210	0.061*
H10C	−0.2078	1.0457	0.1313	0.061*
C11	0.8011 (5)	0.5326 (3)	0.3952 (2)	0.0345 (6)
H11A	0.8868	0.4773	0.3628	0.052*
H11B	0.7535	0.4826	0.4745	0.052*
H11C	0.8980	0.5958	0.3938	0.052*
C12	0.3727 (4)	0.3601 (2)	0.2543 (2)	0.0236 (5)
H12	0.2168	0.4061	0.2405	0.028*
C13	0.4062 (5)	0.2963 (3)	0.3826 (2)	0.0361 (6)
H13A	0.3831	0.3599	0.4157	0.043*
H13B	0.5643	0.2562	0.3976	0.043*
C14	0.2387 (6)	0.1967 (3)	0.4400 (2)	0.0447 (7)
H14A	0.2694	0.1530	0.5228	0.054*
H14B	0.0811	0.2381	0.4320	0.054*
C15	0.2590 (6)	0.1012 (3)	0.3867 (3)	0.0442 (7)
H15A	0.1432	0.0407	0.4226	0.053*
H15B	0.4116	0.0538	0.4016	0.053*
C16	0.2251 (5)	0.1658 (3)	0.2582 (2)	0.0380 (6)
H16A	0.0671	0.2061	0.2437	0.046*
H16B	0.2464	0.1021	0.2251	0.046*
C17	0.3923 (5)	0.2649 (2)	0.1994 (2)	0.0312 (5)
H17A	0.3592	0.3091	0.1169	0.037*
H17B	0.5499	0.2237	0.2064	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.02588 (14)	0.03838 (16)	0.03727 (16)	0.00417 (10)	−0.00621 (10)	−0.00237 (11)
S1	0.0252 (3)	0.0267 (3)	0.0457 (4)	−0.0040 (2)	0.0114 (3)	−0.0168 (3)
O1	0.0262 (9)	0.0269 (8)	0.0338 (9)	−0.0042 (7)	−0.0043 (7)	−0.0140 (7)
O2A	0.0242 (10)	0.0408 (13)	0.0592 (16)	0.0009 (8)	0.0026 (9)	−0.0238 (11)
O2B	0.036 (8)	0.037 (7)	0.0463 (14)	−0.002 (5)	0.009 (2)	−0.029 (5)
C1	0.0189 (11)	0.0204 (10)	0.0280 (11)	−0.0024 (8)	0.0018 (9)	−0.0082 (9)
C2	0.0185 (11)	0.0198 (10)	0.0274 (11)	−0.0033 (8)	0.0016 (9)	−0.0086 (9)
C3	0.0201 (11)	0.0214 (10)	0.0247 (11)	−0.0036 (8)	0.0019 (9)	−0.0059 (9)
C4	0.0201 (11)	0.0221 (10)	0.0294 (12)	−0.0022 (8)	0.0003 (9)	−0.0028 (9)
C5	0.0250 (12)	0.0194 (10)	0.0373 (13)	−0.0025 (9)	0.0080 (10)	−0.0075 (10)
C6	0.0321 (13)	0.0223 (11)	0.0348 (13)	−0.0063 (9)	0.0051 (10)	−0.0138 (10)
C7	0.0237 (11)	0.0228 (10)	0.0269 (11)	−0.0059 (9)	0.0002 (9)	−0.0086 (9)
C8	0.0216 (11)	0.0238 (11)	0.0332 (13)	−0.0042 (9)	−0.0006 (9)	−0.0078 (10)
C9	0.0275 (12)	0.0318 (12)	0.0278 (12)	−0.0014 (10)	−0.0037 (10)	−0.0116 (10)
C10	0.0358 (15)	0.0259 (12)	0.0544 (18)	0.0032 (11)	0.0080 (13)	−0.0143 (12)
C11	0.0257 (13)	0.0370 (14)	0.0360 (14)	−0.0034 (10)	−0.0073 (11)	−0.0089 (11)
C12	0.0211 (11)	0.0225 (10)	0.0277 (11)	−0.0013 (8)	0.0014 (9)	−0.0110 (9)
C13	0.0481 (17)	0.0338 (13)	0.0275 (13)	−0.0066 (12)	−0.0022 (11)	−0.0124 (11)
C14	0.068 (2)	0.0347 (14)	0.0303 (14)	−0.0148 (14)	0.0144 (14)	−0.0118 (12)
C15	0.062 (2)	0.0276 (13)	0.0407 (16)	−0.0113 (13)	0.0105 (14)	−0.0115 (12)
C16	0.0459 (17)	0.0315 (13)	0.0416 (15)	−0.0113 (12)	0.0049 (13)	−0.0190 (12)
C17	0.0396 (15)	0.0261 (11)	0.0302 (13)	−0.0045 (10)	0.0038 (11)	−0.0141 (10)

Br1—C4	1.903 (2)	C10—H10A	0.9800
Br1—Br1i	3.6838 (6)	C10—H10B	0.9800
S1—O2B	1.450 (2)	C10—H10C	0.9800
S1—O2A	1.451 (2)	C11—H11A	0.9800
S1—C1	1.778 (2)	C11—H11B	0.9800
S1—C12	1.830 (2)	C11—H11C	0.9800
O1—C7	1.373 (3)	C12—C13	1.516 (3)
O1—C8	1.381 (3)	C12—C17	1.531 (3)
C1—C8	1.353 (3)	C12—H12	1.0000
C1—C2	1.457 (3)	C13—C14	1.528 (4)
C2—C7	1.392 (3)	C13—H13A	0.9900
C2—C3	1.411 (3)	C13—H13B	0.9900
C3—C4	1.397 (3)	C14—C15	1.519 (4)
C3—C9	1.501 (3)	C14—H14A	0.9900
C4—C5	1.412 (4)	C14—H14B	0.9900
C5—C6	1.379 (4)	C15—C16	1.520 (4)
C5—C10	1.506 (3)	C15—H15A	0.9900
C6—C7	1.379 (3)	C15—H15B	0.9900
C6—H6	0.9500	C16—C17	1.526 (4)
C8—C11	1.482 (3)	C16—H16A	0.9900
C9—H9A	0.9800	C16—H16B	0.9900
C9—H9B	0.9800	C17—H17A	0.9900
C9—H9C	0.9800	C17—H17B	0.9900
C4—Br1—Br1i	129.48 (8)	H10B—C10—H10C	109.5
O2B—S1—O2A	97.6 (6)	C8—C11—H11A	109.5
O2B—S1—C1	119.2 (5)	C8—C11—H11B	109.5
O2A—S1—C1	110.03 (13)	H11A—C11—H11B	109.5
O2B—S1—C12	123.9 (6)	C8—C11—H11C	109.5
O2A—S1—C12	107.98 (13)	H11A—C11—H11C	109.5
C1—S1—C12	97.78 (11)	H11B—C11—H11C	109.5
C7—O1—C8	106.35 (18)	C13—C12—C17	111.8 (2)
C8—C1—C2	106.9 (2)	C13—C12—S1	112.15 (18)
C8—C1—S1	125.76 (19)	C17—C12—S1	107.30 (17)
C2—C1—S1	127.31 (18)	C13—C12—H12	108.5
C7—C2—C3	119.2 (2)	C17—C12—H12	108.5
C7—C2—C1	104.7 (2)	S1—C12—H12	108.5
C3—C2—C1	136.1 (2)	C12—C13—C14	110.8 (2)
C4—C3—C2	115.2 (2)	C12—C13—H13A	109.5
C4—C3—C9	122.7 (2)	C14—C13—H13A	109.5
C2—C3—C9	122.1 (2)	C12—C13—H13B	109.5
C3—C4—C5	125.2 (2)	C14—C13—H13B	109.5
C3—C4—Br1	118.04 (19)	H13A—C13—H13B	108.1
C5—C4—Br1	116.76 (18)	C15—C14—C13	111.2 (2)
C6—C5—C4	117.9 (2)	C15—C14—H14A	109.4
C6—C5—C10	120.1 (2)	C13—C14—H14A	109.4
C4—C5—C10	122.0 (2)	C15—C14—H14B	109.4
C7—C6—C5	117.9 (2)	C13—C14—H14B	109.4
C7—C6—H6	121.1	H14A—C14—H14B	108.0
C5—C6—H6	121.1	C14—C15—C16	110.9 (2)
O1—C7—C6	124.6 (2)	C14—C15—H15A	109.5
O1—C7—C2	110.9 (2)	C16—C15—H15A	109.5
C6—C7—C2	124.5 (2)	C14—C15—H15B	109.5
C1—C8—O1	111.1 (2)	C16—C15—H15B	109.5
C1—C8—C11	134.8 (2)	H15A—C15—H15B	108.0
O1—C8—C11	114.1 (2)	C15—C16—C17	111.6 (2)
C3—C9—H9A	109.5	C15—C16—H16A	109.3
C3—C9—H9B	109.5	C17—C16—H16A	109.3
H9A—C9—H9B	109.5	C15—C16—H16B	109.3
C3—C9—H9C	109.5	C17—C16—H16B	109.3
H9A—C9—H9C	109.5	H16A—C16—H16B	108.0
H9B—C9—H9C	109.5	C16—C17—C12	110.3 (2)
C5—C10—H10A	109.5	C16—C17—H17A	109.6
C5—C10—H10B	109.5	C12—C17—H17A	109.6
H10A—C10—H10B	109.5	C16—C17—H17B	109.6
C5—C10—H10C	109.5	C12—C17—H17B	109.6
H10A—C10—H10C	109.5	H17A—C17—H17B	108.1
O2B—S1—C1—C8	−120.2 (7)	C8—O1—C7—C2	−1.0 (3)
O2A—S1—C1—C8	−8.9 (3)	C5—C6—C7—O1	179.1 (2)
C12—S1—C1—C8	103.5 (2)	C5—C6—C7—C2	−0.8 (4)
O2B—S1—C1—C2	58.4 (7)	C3—C2—C7—O1	−177.3 (2)
O2A—S1—C1—C2	169.7 (2)	C1—C2—C7—O1	1.4 (3)
C12—S1—C1—C2	−77.8 (2)	C3—C2—C7—C6	2.7 (4)
C8—C1—C2—C7	−1.3 (3)	C1—C2—C7—C6	−178.6 (2)
S1—C1—C2—C7	179.92 (17)	C2—C1—C8—O1	0.7 (3)
C8—C1—C2—C3	177.1 (3)	S1—C1—C8—O1	179.52 (16)
S1—C1—C2—C3	−1.7 (4)	C2—C1—C8—C11	179.9 (3)
C7—C2—C3—C4	−2.7 (3)	S1—C1—C8—C11	−1.2 (4)
C1—C2—C3—C4	179.2 (2)	C7—O1—C8—C1	0.2 (3)
C7—C2—C3—C9	176.6 (2)	C7—O1—C8—C11	−179.2 (2)
C1—C2—C3—C9	−1.6 (4)	O2B—S1—C12—C13	160.6 (7)
C2—C3—C4—C5	1.1 (3)	O2A—S1—C12—C13	47.9 (2)
C9—C3—C4—C5	−178.1 (2)	C1—S1—C12—C13	−66.1 (2)
C2—C3—C4—Br1	−179.22 (16)	O2B—S1—C12—C17	37.5 (7)
C9—C3—C4—Br1	1.5 (3)	O2A—S1—C12—C17	−75.2 (2)
Br1i—Br1—C4—C3	−175.07 (14)	C1—S1—C12—C17	170.76 (17)
Br1i—Br1—C4—C5	4.6 (2)	C17—C12—C13—C14	−55.7 (3)
C3—C4—C5—C6	0.7 (4)	S1—C12—C13—C14	−176.3 (2)
Br1—C4—C5—C6	−179.00 (18)	C12—C13—C14—C15	55.8 (4)
C3—C4—C5—C10	179.6 (2)	C13—C14—C15—C16	−56.1 (4)
Br1—C4—C5—C10	0.0 (3)	C14—C15—C16—C17	56.3 (4)
C4—C5—C6—C7	−0.8 (3)	C15—C16—C17—C12	−55.5 (3)
C10—C5—C6—C7	−179.8 (2)	C13—C12—C17—C16	55.4 (3)
C8—O1—C7—C6	179.0 (2)	S1—C12—C17—C16	178.79 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2Aii	1.00	2.44	3.355 (3)	151
C11—H11C···Cg1iii	0.98	2.83	3.547 (3)	130

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
C12—H12⋯O2A i	1.00	2.44	3.355 (3)	151
C11—H11C⋯Cg1ii	0.98	2.83	3.547 (3)	130

Symmetry codes: (i) ; (ii) .