3-(3-Chloro-phenyl-sulfon-yl)-5-isopropyl-2-methyl-1-benzofuran.

In the title compound, C(18)H(17)ClO(3)S, the 3-chloro-benzene ring makes a dihedral angle of 82.04 (5)° with the mean plane [r.m.s. deviation = 0.006 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C18H17ClO3S

M = 348.83

Triclinic,

a = 7.1700 (2) Å

b = 9.9400 (2) Å

c = 12.2508 (3) Å

α = 83.484 (1)°

β = 77.907 (1)°

γ = 85.707 (1)°

V = 847.05 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 173 K

0.29 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.903, T max = 0.955

16044 measured reflections

4231 independent reflections

3596 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.132

S = 1.06

4231 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.46 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/S1600536812008525/lr2052sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008525/lr2052Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008525/lr2052Isup3.cml

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

C18H17ClO3S	Z = 2
Mr = 348.83	F(000) = 364
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1700 (2) Å	Cell parameters from 7011 reflections
b = 9.9400 (2) Å	θ = 2.6–28.4°
c = 12.2508 (3) Å	µ = 0.36 mm−1
α = 83.484 (1)°	T = 173 K
β = 77.907 (1)°	Block, colourless
γ = 85.707 (1)°	0.29 × 0.24 × 0.13 mm
V = 847.05 (4) Å3

Bruker SMART APEXII CCD diffractometer	4231 independent reflections
Radiation source: rotating anode	3596 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 1.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.903, Tmax = 0.955	l = −16→16
16044 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F2) = 0.132	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0688P)2 + 0.4272P] where P = (Fo2 + 2Fc2)/3
4231 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.46 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
Cl1	0.22055 (7)	0.49026 (6)	0.63396 (4)	0.04596 (16)
S1	0.34765 (7)	0.31464 (4)	0.22246 (3)	0.03083 (13)
O1	0.71701 (19)	0.58220 (14)	0.07545 (10)	0.0376 (3)
O2	0.1494 (2)	0.35118 (15)	0.22738 (12)	0.0418 (3)
O3	0.4313 (3)	0.19619 (14)	0.17075 (12)	0.0470 (4)
C1	0.4757 (2)	0.45364 (16)	0.16032 (13)	0.0269 (3)
C2	0.4074 (3)	0.59381 (16)	0.16760 (13)	0.0287 (3)
C3	0.2339 (3)	0.66147 (18)	0.21091 (15)	0.0350 (4)
H3	0.1263	0.6116	0.2471	0.042*
C4	0.2210 (3)	0.8016 (2)	0.20043 (17)	0.0424 (5)
C5	0.3805 (4)	0.8721 (2)	0.14704 (18)	0.0485 (5)
H5	0.3705	0.9684	0.1413	0.058*
C6	0.5538 (4)	0.8085 (2)	0.10175 (18)	0.0476 (5)
H6	0.6607	0.8585	0.0645	0.057*
C7	0.5627 (3)	0.66778 (19)	0.11380 (14)	0.0346 (4)
C8	0.6615 (3)	0.45245 (18)	0.10554 (14)	0.0314 (4)
C9	0.0286 (4)	0.8735 (2)	0.2472 (2)	0.0510 (5)
H9	−0.0715	0.8055	0.2589	0.061*
C10	0.0305 (5)	0.9199 (4)	0.3600 (2)	0.0800 (10)
H10A	0.1277	0.9867	0.3513	0.120*
H10B	0.0601	0.8419	0.4112	0.120*
H10C	−0.0952	0.9612	0.3907	0.120*
C11	−0.0257 (5)	0.9892 (3)	0.1681 (3)	0.0735 (8)
H11A	−0.1572	1.0223	0.1965	0.110*
H11B	−0.0162	0.9582	0.0939	0.110*
H11C	0.0608	1.0626	0.1622	0.110*
C12	0.8097 (3)	0.3445 (2)	0.07479 (18)	0.0445 (5)
H12A	0.8950	0.3338	0.1285	0.067*
H12B	0.8836	0.3690	−0.0008	0.067*
H12C	0.7490	0.2590	0.0763	0.067*
C13	0.3857 (3)	0.29535 (17)	0.36169 (14)	0.0301 (3)
C14	0.2933 (2)	0.38686 (17)	0.43515 (14)	0.0300 (3)
H14	0.2060	0.4559	0.4127	0.036*
C15	0.3317 (3)	0.3750 (2)	0.54204 (14)	0.0337 (4)
C16	0.4560 (3)	0.2732 (2)	0.57601 (17)	0.0448 (5)
H16	0.4809	0.2661	0.6497	0.054*
C17	0.5430 (4)	0.1826 (2)	0.50199 (19)	0.0509 (5)
H17	0.6268	0.1117	0.5254	0.061*
C18	0.5105 (3)	0.1929 (2)	0.39347 (17)	0.0425 (4)
H18	0.5727	0.1309	0.3422	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0426 (3)	0.0637 (3)	0.0318 (2)	−0.0110 (2)	0.00138 (19)	−0.0171 (2)
S1	0.0390 (2)	0.0288 (2)	0.0274 (2)	−0.00753 (17)	−0.00952 (17)	−0.00579 (15)
O1	0.0365 (7)	0.0478 (8)	0.0290 (6)	−0.0133 (6)	−0.0028 (5)	−0.0056 (6)
O2	0.0366 (7)	0.0537 (8)	0.0395 (7)	−0.0132 (6)	−0.0144 (6)	−0.0029 (6)
O3	0.0747 (11)	0.0293 (6)	0.0396 (7)	−0.0061 (7)	−0.0112 (7)	−0.0126 (6)
C1	0.0312 (8)	0.0283 (7)	0.0227 (7)	−0.0026 (6)	−0.0075 (6)	−0.0047 (6)
C2	0.0369 (9)	0.0279 (8)	0.0223 (7)	−0.0019 (7)	−0.0080 (6)	−0.0036 (6)
C3	0.0419 (10)	0.0341 (9)	0.0295 (8)	0.0035 (7)	−0.0087 (7)	−0.0057 (7)
C4	0.0611 (13)	0.0339 (9)	0.0339 (9)	0.0078 (9)	−0.0154 (9)	−0.0060 (7)
C5	0.0783 (16)	0.0285 (9)	0.0412 (11)	0.0013 (10)	−0.0184 (11)	−0.0053 (8)
C6	0.0684 (15)	0.0405 (10)	0.0359 (10)	−0.0230 (10)	−0.0118 (10)	0.0035 (8)
C7	0.0452 (10)	0.0355 (9)	0.0241 (8)	−0.0089 (8)	−0.0070 (7)	−0.0032 (6)
C8	0.0336 (9)	0.0399 (9)	0.0230 (7)	−0.0023 (7)	−0.0084 (6)	−0.0084 (7)
C9	0.0598 (14)	0.0427 (11)	0.0509 (12)	0.0112 (10)	−0.0137 (11)	−0.0104 (9)
C10	0.0746 (19)	0.110 (3)	0.0598 (16)	0.0405 (18)	−0.0238 (15)	−0.0397 (17)
C11	0.0756 (19)	0.0659 (17)	0.080 (2)	0.0106 (15)	−0.0291 (16)	0.0048 (15)
C12	0.0342 (10)	0.0599 (13)	0.0421 (10)	0.0094 (9)	−0.0111 (8)	−0.0176 (9)
C13	0.0352 (9)	0.0282 (8)	0.0275 (8)	−0.0057 (7)	−0.0076 (7)	−0.0010 (6)
C14	0.0290 (8)	0.0333 (8)	0.0284 (8)	−0.0054 (7)	−0.0060 (6)	−0.0035 (6)
C15	0.0316 (9)	0.0432 (10)	0.0258 (8)	−0.0117 (7)	−0.0018 (7)	−0.0031 (7)
C16	0.0506 (12)	0.0543 (12)	0.0317 (9)	−0.0072 (10)	−0.0153 (9)	0.0032 (8)
C17	0.0606 (14)	0.0468 (12)	0.0465 (12)	0.0093 (10)	−0.0224 (11)	0.0039 (9)
C18	0.0513 (12)	0.0353 (9)	0.0404 (10)	0.0065 (8)	−0.0114 (9)	−0.0040 (8)

Cl1—C15	1.7307 (19)	C9—C10	1.509 (4)
S1—O2	1.4308 (15)	C9—H9	1.0000
S1—O3	1.4325 (14)	C10—H10A	0.9800
S1—C1	1.7290 (17)	C10—H10B	0.9800
S1—C13	1.7700 (18)	C10—H10C	0.9800
O1—C8	1.366 (2)	C11—H11A	0.9800
O1—C7	1.379 (2)	C11—H11B	0.9800
C1—C8	1.360 (2)	C11—H11C	0.9800
C1—C2	1.448 (2)	C12—H12A	0.9800
C2—C7	1.386 (3)	C12—H12B	0.9800
C2—C3	1.400 (2)	C12—H12C	0.9800
C3—C4	1.382 (3)	C13—C18	1.382 (3)
C3—H3	0.9500	C13—C14	1.386 (2)
C4—C5	1.389 (3)	C14—C15	1.384 (2)
C4—C9	1.534 (3)	C14—H14	0.9500
C5—C6	1.387 (3)	C15—C16	1.385 (3)
C5—H5	0.9500	C16—C17	1.374 (3)
C6—C7	1.387 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—C18	1.388 (3)
C8—C12	1.475 (3)	C17—H17	0.9500
C9—C11	1.501 (3)	C18—H18	0.9500
O2—S1—O3	119.69 (9)	C9—C10—H10A	109.5
O2—S1—C1	107.76 (8)	C9—C10—H10B	109.5
O3—S1—C1	109.52 (9)	H10A—C10—H10B	109.5
O2—S1—C13	107.50 (8)	C9—C10—H10C	109.5
O3—S1—C13	107.43 (9)	H10A—C10—H10C	109.5
C1—S1—C13	103.79 (8)	H10B—C10—H10C	109.5
C8—O1—C7	107.30 (14)	C9—C11—H11A	109.5
C8—C1—C2	107.79 (15)	C9—C11—H11B	109.5
C8—C1—S1	126.80 (14)	H11A—C11—H11B	109.5
C2—C1—S1	125.15 (13)	C9—C11—H11C	109.5
C7—C2—C3	119.77 (16)	H11A—C11—H11C	109.5
C7—C2—C1	104.46 (16)	H11B—C11—H11C	109.5
C3—C2—C1	135.75 (17)	C8—C12—H12A	109.5
C4—C3—C2	119.30 (19)	C8—C12—H12B	109.5
C4—C3—H3	120.3	H12A—C12—H12B	109.5
C2—C3—H3	120.3	C8—C12—H12C	109.5
C3—C4—C5	119.2 (2)	H12A—C12—H12C	109.5
C3—C4—C9	118.4 (2)	H12B—C12—H12C	109.5
C5—C4—C9	122.43 (19)	C18—C13—C14	121.69 (17)
C6—C5—C4	123.05 (18)	C18—C13—S1	119.55 (14)
C6—C5—H5	118.5	C14—C13—S1	118.73 (14)
C4—C5—H5	118.5	C15—C14—C13	118.22 (17)
C7—C6—C5	116.5 (2)	C15—C14—H14	120.9
C7—C6—H6	121.8	C13—C14—H14	120.9
C5—C6—H6	121.8	C14—C15—C16	121.22 (18)
O1—C7—C2	110.48 (15)	C14—C15—Cl1	118.77 (15)
O1—C7—C6	127.30 (18)	C16—C15—Cl1	120.01 (15)
C2—C7—C6	122.21 (19)	C17—C16—C15	119.26 (19)
C1—C8—O1	109.96 (15)	C17—C16—H16	120.4
C1—C8—C12	134.29 (18)	C15—C16—H16	120.4
O1—C8—C12	115.74 (16)	C16—C17—C18	121.1 (2)
C11—C9—C10	111.0 (2)	C16—C17—H17	119.5
C11—C9—C4	112.9 (2)	C18—C17—H17	119.5
C10—C9—C4	110.2 (2)	C13—C18—C17	118.53 (19)
C11—C9—H9	107.5	C13—C18—H18	120.7
C10—C9—H9	107.5	C17—C18—H18	120.7
C4—C9—H9	107.5
O2—S1—C1—C8	−156.03 (15)	S1—C1—C8—O1	−175.31 (11)
O3—S1—C1—C8	−24.32 (18)	C2—C1—C8—C12	178.02 (19)
C13—S1—C1—C8	90.16 (16)	S1—C1—C8—C12	3.6 (3)
O2—S1—C1—C2	30.48 (16)	C7—O1—C8—C1	0.90 (19)
O3—S1—C1—C2	162.19 (14)	C7—O1—C8—C12	−178.25 (15)
C13—S1—C1—C2	−83.33 (16)	C3—C4—C9—C11	−135.1 (2)
C8—C1—C2—C7	0.54 (18)	C5—C4—C9—C11	44.1 (3)
S1—C1—C2—C7	175.07 (13)	C3—C4—C9—C10	100.2 (3)
C8—C1—C2—C3	178.83 (19)	C5—C4—C9—C10	−80.7 (3)
S1—C1—C2—C3	−6.6 (3)	O2—S1—C13—C18	141.75 (16)
C7—C2—C3—C4	−0.7 (3)	O3—S1—C13—C18	11.71 (19)
C1—C2—C3—C4	−178.83 (18)	C1—S1—C13—C18	−104.25 (17)
C2—C3—C4—C5	0.0 (3)	O2—S1—C13—C14	−40.32 (16)
C2—C3—C4—C9	179.19 (17)	O3—S1—C13—C14	−170.36 (14)
C3—C4—C5—C6	0.9 (3)	C1—S1—C13—C14	73.68 (15)
C9—C4—C5—C6	−178.2 (2)	C18—C13—C14—C15	1.1 (3)
C4—C5—C6—C7	−1.1 (3)	S1—C13—C14—C15	−176.74 (13)
C8—O1—C7—C2	−0.54 (19)	C13—C14—C15—C16	−1.2 (3)
C8—O1—C7—C6	−179.70 (19)	C13—C14—C15—Cl1	178.92 (13)
C3—C2—C7—O1	−178.62 (15)	C14—C15—C16—C17	0.1 (3)
C1—C2—C7—O1	0.00 (19)	Cl1—C15—C16—C17	−179.99 (17)
C3—C2—C7—C6	0.6 (3)	C15—C16—C17—C18	1.0 (4)
C1—C2—C7—C6	179.21 (17)	C14—C13—C18—C17	0.0 (3)
C5—C6—C7—O1	179.36 (18)	S1—C13—C18—C17	177.84 (17)
C5—C6—C7—C2	0.3 (3)	C16—C17—C18—C13	−1.1 (4)
C2—C1—C8—O1	−0.90 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3i	0.95	2.42	3.321 (2)	159
C12—H12A···O2ii	0.98	2.42	3.375 (2)	165
C16—H16···Cgiii	0.95	2.71	3.646 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3i	0.95	2.42	3.321 (2)	159
C12—H12A⋯O2ii	0.98	2.42	3.375 (2)	165
C16—H16⋯Cgiii	0.95	2.71	3.646 (2)	170

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