3-(3-Chloro-phenyl-sulfon-yl)-2,5,7-trimethyl-1-benzofuran.

In the title compound, C(17)H(15)ClO(3)S, the 3-chloro-phenyl ring makes a dihedral angle of 77.76 (6)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular 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. (2008 ▶, 2010 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C17H15ClO3S

M = 334.80

Monoclinic,

a = 14.5299 (3) Å

b = 12.9778 (2) Å

c = 8.1776 (1) Å

β = 92.615 (1)°

V = 1540.41 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 173 K

0.36 × 0.29 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.872, T max = 0.908

14420 measured reflections

3551 independent reflections

3053 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.04

3551 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.41 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/S1600536812008355/bh2417sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008355/bh2417Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008355/bh2417Isup3.cml

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

C17H15ClO3S	F(000) = 696
Mr = 334.80	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Melting point: 413 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.5299 (3) Å	Cell parameters from 7514 reflections
b = 12.9778 (2) Å	θ = 2.8–27.4°
c = 8.1776 (1) Å	µ = 0.39 mm−1
β = 92.615 (1)°	T = 173 K
V = 1540.41 (4) Å3	Block, colourless
Z = 4	0.36 × 0.29 × 0.25 mm

Bruker SMART APEXII CCD diffractometer	3551 independent reflections
Radiation source: rotating anode	3053 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.4°
φ and ω scans	h = −15→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→16
Tmin = 0.872, Tmax = 0.908	l = −10→10
14420 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) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.775P] where P = (Fo2 + 2Fc2)/3
3551 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.41 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cl1	0.11297 (3)	0.26899 (4)	0.95927 (6)	0.03925 (14)
S1	0.38836 (3)	0.46155 (3)	0.65400 (5)	0.02434 (12)
O1	0.32039 (8)	0.75011 (9)	0.56955 (15)	0.0285 (3)
O2	0.35944 (9)	0.38758 (10)	0.53201 (14)	0.0313 (3)
O3	0.48438 (8)	0.47396 (10)	0.69791 (15)	0.0325 (3)
C1	0.34200 (11)	0.57998 (13)	0.59670 (19)	0.0242 (3)
C2	0.25351 (11)	0.59471 (13)	0.51051 (18)	0.0234 (3)
C3	0.18368 (12)	0.53119 (13)	0.4455 (2)	0.0265 (4)
H3	0.1880	0.4584	0.4548	0.032*
C4	0.10747 (12)	0.57732 (15)	0.3666 (2)	0.0297 (4)
C5	0.10147 (12)	0.68466 (15)	0.3578 (2)	0.0305 (4)
H5	0.0485	0.7142	0.3040	0.037*
C6	0.16886 (12)	0.75061 (14)	0.4236 (2)	0.0281 (4)
C7	0.24429 (11)	0.70102 (13)	0.49726 (19)	0.0252 (3)
C8	0.37838 (12)	0.67465 (14)	0.6292 (2)	0.0278 (4)
C9	0.03198 (14)	0.51129 (17)	0.2890 (3)	0.0404 (5)
H9A	0.0450	0.4981	0.1743	0.061*
H9B	−0.0271	0.5472	0.2943	0.061*
H9C	0.0291	0.4457	0.3479	0.061*
C10	0.16093 (14)	0.86578 (15)	0.4170 (3)	0.0381 (4)
H10A	0.1800	0.8948	0.5239	0.057*
H10B	0.0969	0.8851	0.3895	0.057*
H10C	0.2007	0.8927	0.3334	0.057*
C11	0.46509 (13)	0.71222 (16)	0.7113 (3)	0.0385 (4)
H11A	0.4854	0.6634	0.7970	0.058*
H11B	0.4544	0.7798	0.7606	0.058*
H11C	0.5127	0.7183	0.6308	0.058*
C12	0.33205 (11)	0.42967 (13)	0.83512 (19)	0.0241 (3)
C13	0.36775 (12)	0.46631 (15)	0.9846 (2)	0.0300 (4)
H13	0.4209	0.5090	0.9896	0.036*
C14	0.32471 (13)	0.43965 (16)	1.1264 (2)	0.0335 (4)
H14	0.3488	0.4634	1.2296	0.040*
C15	0.24674 (13)	0.37856 (14)	1.1179 (2)	0.0308 (4)
H15	0.2174	0.3597	1.2150	0.037*
C16	0.21193 (12)	0.34517 (13)	0.9675 (2)	0.0273 (4)
C17	0.25354 (11)	0.36921 (13)	0.8236 (2)	0.0253 (3)
H17	0.2292	0.3452	0.7208	0.030*

	U11	U22	U33	U12	U13	U23
Cl1	0.0390 (3)	0.0409 (3)	0.0380 (3)	−0.0132 (2)	0.0041 (2)	0.0024 (2)
S1	0.0259 (2)	0.0245 (2)	0.0226 (2)	0.00192 (15)	0.00121 (15)	0.00141 (15)
O1	0.0278 (6)	0.0236 (6)	0.0338 (7)	−0.0011 (5)	−0.0036 (5)	0.0008 (5)
O2	0.0416 (7)	0.0275 (7)	0.0249 (6)	0.0006 (5)	0.0037 (5)	−0.0028 (5)
O3	0.0252 (6)	0.0372 (7)	0.0352 (7)	0.0032 (5)	0.0020 (5)	0.0056 (6)
C1	0.0245 (8)	0.0261 (9)	0.0219 (7)	0.0003 (6)	−0.0005 (6)	0.0014 (6)
C2	0.0245 (8)	0.0262 (8)	0.0196 (7)	0.0003 (6)	0.0021 (6)	0.0008 (6)
C3	0.0291 (8)	0.0255 (9)	0.0249 (8)	−0.0021 (7)	0.0016 (6)	−0.0008 (7)
C4	0.0263 (8)	0.0377 (10)	0.0251 (8)	−0.0039 (7)	−0.0003 (7)	−0.0010 (7)
C5	0.0242 (8)	0.0373 (10)	0.0298 (8)	0.0037 (7)	−0.0003 (7)	0.0040 (7)
C6	0.0278 (8)	0.0295 (9)	0.0273 (8)	0.0036 (7)	0.0040 (7)	0.0039 (7)
C7	0.0262 (8)	0.0260 (9)	0.0233 (8)	−0.0019 (6)	0.0006 (6)	0.0002 (7)
C8	0.0275 (8)	0.0283 (9)	0.0273 (8)	0.0005 (7)	−0.0008 (7)	0.0011 (7)
C9	0.0328 (10)	0.0460 (12)	0.0417 (11)	−0.0079 (9)	−0.0073 (8)	−0.0002 (9)
C10	0.0379 (10)	0.0305 (10)	0.0456 (11)	0.0052 (8)	0.0001 (8)	0.0059 (8)
C11	0.0329 (9)	0.0353 (11)	0.0463 (11)	−0.0057 (8)	−0.0092 (8)	−0.0038 (9)
C12	0.0254 (8)	0.0240 (8)	0.0227 (7)	0.0033 (6)	0.0005 (6)	0.0014 (6)
C13	0.0258 (8)	0.0373 (10)	0.0263 (8)	−0.0014 (7)	−0.0033 (7)	−0.0013 (7)
C14	0.0361 (10)	0.0419 (11)	0.0220 (8)	0.0005 (8)	−0.0038 (7)	−0.0032 (7)
C15	0.0360 (9)	0.0336 (10)	0.0229 (8)	0.0031 (7)	0.0035 (7)	0.0021 (7)
C16	0.0285 (8)	0.0235 (8)	0.0298 (8)	−0.0006 (7)	0.0013 (7)	0.0018 (7)
C17	0.0305 (8)	0.0230 (8)	0.0221 (7)	0.0010 (7)	−0.0019 (6)	−0.0007 (6)

Cl1—C16	1.7437 (18)	C9—H9A	0.9800
S1—O2	1.4336 (13)	C9—H9B	0.9800
S1—O3	1.4337 (13)	C9—H9C	0.9800
S1—C1	1.7341 (17)	C10—H10A	0.9800
S1—C12	1.7734 (16)	C10—H10B	0.9800
O1—C8	1.367 (2)	C10—H10C	0.9800
O1—C7	1.385 (2)	C11—H11A	0.9800
C1—C8	1.359 (2)	C11—H11B	0.9800
C1—C2	1.450 (2)	C11—H11C	0.9800
C2—C7	1.390 (2)	C12—C17	1.384 (2)
C2—C3	1.394 (2)	C12—C13	1.390 (2)
C3—C4	1.391 (2)	C13—C14	1.386 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.397 (3)	C14—C15	1.382 (3)
C4—C9	1.509 (3)	C14—H14	0.9500
C5—C6	1.390 (3)	C15—C16	1.378 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.385 (2)	C16—C17	1.383 (2)
C6—C10	1.500 (3)	C17—H17	0.9500
C8—C11	1.483 (2)
O2—S1—O3	120.04 (8)	C4—C9—H9C	109.5
O2—S1—C1	107.91 (8)	H9A—C9—H9C	109.5
O3—S1—C1	109.25 (8)	H9B—C9—H9C	109.5
O2—S1—C12	107.05 (8)	C6—C10—H10A	109.5
O3—S1—C12	107.32 (8)	C6—C10—H10B	109.5
C1—S1—C12	104.13 (8)	H10A—C10—H10B	109.5
C8—O1—C7	106.84 (13)	C6—C10—H10C	109.5
C8—C1—C2	107.71 (15)	H10A—C10—H10C	109.5
C8—C1—S1	127.28 (13)	H10B—C10—H10C	109.5
C2—C1—S1	124.96 (13)	C8—C11—H11A	109.5
C7—C2—C3	119.44 (15)	C8—C11—H11B	109.5
C7—C2—C1	104.41 (15)	H11A—C11—H11B	109.5
C3—C2—C1	136.15 (16)	C8—C11—H11C	109.5
C4—C3—C2	118.20 (16)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C17—C12—C13	121.80 (15)
C3—C4—C5	119.95 (16)	C17—C12—S1	119.06 (12)
C3—C4—C9	119.90 (17)	C13—C12—S1	119.14 (13)
C5—C4—C9	120.15 (17)	C14—C13—C12	119.07 (16)
C6—C5—C4	123.56 (16)	C14—C13—H13	120.5
C6—C5—H5	118.2	C12—C13—H13	120.5
C4—C5—H5	118.2	C15—C14—C13	120.09 (16)
C7—C6—C5	114.31 (16)	C15—C14—H14	120.0
C7—C6—C10	122.45 (17)	C13—C14—H14	120.0
C5—C6—C10	123.24 (17)	C16—C15—C14	119.46 (16)
C6—C7—O1	124.92 (16)	C16—C15—H15	120.3
C6—C7—C2	124.52 (16)	C14—C15—H15	120.3
O1—C7—C2	110.55 (14)	C15—C16—C17	122.10 (16)
C1—C8—O1	110.49 (14)	C15—C16—Cl1	118.76 (13)
C1—C8—C11	134.48 (17)	C17—C16—Cl1	119.14 (13)
O1—C8—C11	115.03 (15)	C16—C17—C12	117.46 (15)
C4—C9—H9A	109.5	C16—C17—H17	121.3
C4—C9—H9B	109.5	C12—C17—H17	121.3
H9A—C9—H9B	109.5
O2—S1—C1—C8	−149.77 (15)	C1—C2—C7—C6	−179.53 (15)
O3—S1—C1—C8	−17.69 (18)	C3—C2—C7—O1	179.81 (14)
C12—S1—C1—C8	96.71 (17)	C1—C2—C7—O1	−0.22 (18)
O2—S1—C1—C2	33.36 (16)	C2—C1—C8—O1	−0.38 (19)
O3—S1—C1—C2	165.44 (13)	S1—C1—C8—O1	−177.69 (12)
C12—S1—C1—C2	−80.16 (15)	C2—C1—C8—C11	−179.72 (19)
C8—C1—C2—C7	0.36 (18)	S1—C1—C8—C11	3.0 (3)
S1—C1—C2—C7	177.75 (12)	C7—O1—C8—C1	0.25 (18)
C8—C1—C2—C3	−179.68 (18)	C7—O1—C8—C11	179.72 (15)
S1—C1—C2—C3	−2.3 (3)	O2—S1—C12—C17	−20.30 (15)
C7—C2—C3—C4	1.1 (2)	O3—S1—C12—C17	−150.40 (13)
C1—C2—C3—C4	−178.86 (17)	C1—S1—C12—C17	93.83 (14)
C2—C3—C4—C5	−1.6 (2)	O2—S1—C12—C13	159.90 (14)
C2—C3—C4—C9	177.74 (16)	O3—S1—C12—C13	29.80 (16)
C3—C4—C5—C6	0.5 (3)	C1—S1—C12—C13	−85.96 (15)
C9—C4—C5—C6	−178.82 (17)	C17—C12—C13—C14	1.5 (3)
C4—C5—C6—C7	1.0 (3)	S1—C12—C13—C14	−178.74 (14)
C4—C5—C6—C10	−178.55 (18)	C12—C13—C14—C15	−0.8 (3)
C5—C6—C7—O1	179.26 (15)	C13—C14—C15—C16	−0.5 (3)
C10—C6—C7—O1	−1.2 (3)	C14—C15—C16—C17	1.2 (3)
C5—C6—C7—C2	−1.5 (2)	C14—C15—C16—Cl1	−179.50 (15)
C10—C6—C7—C2	178.05 (17)	C15—C16—C17—C12	−0.6 (3)
C8—O1—C7—C6	179.31 (16)	Cl1—C16—C17—C12	−179.88 (13)
C8—O1—C7—C2	0.00 (18)	C13—C12—C17—C16	−0.8 (2)
C3—C2—C7—C6	0.5 (3)	S1—C12—C17—C16	179.45 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3i	0.95	2.60	3.264 (2)	127
C10—H10A···Cg2ii	0.98	2.86	3.704 (2)	145
C10—H10C···Cg1ii	0.98	3.08	3.536 (2)	110

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C12–C17 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3i	0.95	2.60	3.264 (2)	127
C10—H10A⋯Cg2ii	0.98	2.86	3.704 (2)	145
C10—H10C⋯Cg1ii	0.98	3.08	3.536 (2)	110

Symmetry codes: (i) ; (ii) .