3-[(4-Chloro-phen-yl)sulfin-yl]-2,4,6,7-tetra-methyl-1-benzofuran.

In the title compound, C(18)H(17)ClO(2)S, the 4-chloro-phenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 87.49 (5)°]. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯π inter-actions, forming left- and right-handed pseudo-helices along the a axis.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 3-(4–chloro­phenyl­sulfin­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C18H17ClO2S

M = 332.83

Orthorhombic,

a = 12.2329 (4) Å

b = 20.1499 (7) Å

c = 6.4840 (2) Å

V = 1598.25 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 173 K

0.33 × 0.16 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.651, T max = 0.746

8651 measured reflections

3392 independent reflections

2809 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.05

3392 reflections

203 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1382 Friedel pairs

Flack parameter: −0.03 (6)

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 datablocks global, I. DOI: 10.1107/S1600536810042339/bh2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042339/bh2316Isup2.hkl

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

C18H17ClO2S	Dx = 1.383 Mg m−3
Mr = 332.83	Melting point: 442 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2945 reflections
a = 12.2329 (4) Å	θ = 2.6–26.8°
b = 20.1499 (7) Å	µ = 0.37 mm−1
c = 6.4840 (2) Å	T = 173 K
V = 1598.25 (9) Å3	Block, colourless
Z = 4	0.33 × 0.16 × 0.10 mm
F(000) = 696

Bruker SMART APEXII CCD diffractometer	3392 independent reflections
Radiation source: rotating anode	2809 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.034
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.0°
φ and ω scans	h = −15→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −26→20
Tmin = 0.651, Tmax = 0.746	l = −8→8
8651 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0426P)2 + 0.1096P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3392 reflections	Δρmax = 0.20 e Å−3
203 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1382 Friedel pairs
0 constraints	Flack parameter: −0.03 (6)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Cl	0.48480 (5)	0.93993 (4)	1.24227 (15)	0.0644 (2)
S	0.37852 (4)	0.74513 (3)	0.51507 (13)	0.03587 (15)
O1	0.64405 (11)	0.64000 (7)	0.4393 (2)	0.0317 (4)
O2	0.27233 (11)	0.71240 (9)	0.5638 (3)	0.0462 (5)
C1	0.48689 (15)	0.68792 (10)	0.5388 (4)	0.0304 (5)
C2	0.51433 (16)	0.63782 (11)	0.6943 (4)	0.0308 (5)
C3	0.47011 (16)	0.61312 (12)	0.8785 (4)	0.0350 (5)
C4	0.52973 (19)	0.56352 (12)	0.9760 (4)	0.0394 (6)
H4	0.5030	0.5469	1.1000	0.047*
C5	0.62780 (17)	0.53683 (12)	0.8996 (4)	0.0368 (6)
C6	0.67069 (16)	0.55999 (10)	0.7143 (4)	0.0331 (5)
C7	0.61165 (16)	0.61008 (11)	0.6216 (4)	0.0301 (5)
C8	0.56685 (15)	0.68753 (11)	0.3949 (4)	0.0312 (5)
C9	0.36522 (17)	0.63876 (14)	0.9713 (4)	0.0443 (7)
H9A	0.3772	0.6823	1.0272	0.066*
H9B	0.3418	0.6094	1.0791	0.066*
H9C	0.3099	0.6409	0.8665	0.066*
C10	0.6861 (2)	0.48422 (12)	1.0225 (5)	0.0506 (7)
H10A	0.7622	0.4953	1.0329	0.076*
H10B	0.6783	0.4421	0.9548	0.076*
H10C	0.6549	0.4817	1.1581	0.076*
C11	0.77427 (18)	0.53408 (12)	0.6181 (4)	0.0423 (6)
H11A	0.8362	0.5515	0.6912	0.063*
H11B	0.7777	0.5477	0.4764	0.063*
H11C	0.7750	0.4865	0.6255	0.063*
C12	0.58942 (18)	0.72823 (11)	0.2117 (4)	0.0370 (5)
H12A	0.6521	0.7557	0.2370	0.055*
H12B	0.5273	0.7557	0.1824	0.055*
H12C	0.6036	0.6998	0.0959	0.055*
C13	0.41185 (16)	0.79762 (10)	0.7289 (4)	0.0322 (5)
C14	0.33260 (16)	0.81193 (11)	0.8759 (4)	0.0353 (5)
H14	0.2642	0.7920	0.8672	0.042*
C15	0.35484 (16)	0.85543 (11)	1.0343 (5)	0.0361 (5)
H15	0.3025	0.8644	1.1346	0.043*
C16	0.45579 (17)	0.88545 (11)	1.0414 (4)	0.0381 (6)
C17	0.53552 (17)	0.87296 (12)	0.8939 (4)	0.0405 (6)
H17	0.6029	0.8942	0.9008	0.049*
C18	0.51360 (16)	0.82887 (11)	0.7378 (4)	0.0367 (6)
H18	0.5663	0.8199	0.6384	0.044*

	U11	U22	U33	U12	U13	U23
Cl	0.0533 (4)	0.0701 (5)	0.0699 (5)	−0.0190 (3)	0.0152 (4)	−0.0291 (4)
S	0.0257 (2)	0.0485 (3)	0.0334 (3)	0.0036 (2)	−0.0013 (3)	0.0026 (3)
O1	0.0293 (6)	0.0334 (8)	0.0324 (9)	0.0032 (6)	0.0014 (7)	0.0023 (7)
O2	0.0239 (7)	0.0632 (11)	0.0516 (12)	−0.0027 (7)	−0.0036 (8)	−0.0053 (9)
C1	0.0256 (9)	0.0357 (12)	0.0299 (12)	−0.0028 (8)	−0.0019 (11)	−0.0005 (11)
C2	0.0251 (9)	0.0363 (13)	0.0310 (13)	−0.0064 (8)	−0.0011 (10)	0.0004 (10)
C3	0.0307 (10)	0.0434 (14)	0.0310 (13)	−0.0115 (10)	0.0007 (11)	0.0016 (11)
C4	0.0425 (12)	0.0428 (14)	0.0330 (15)	−0.0160 (10)	−0.0024 (11)	0.0065 (11)
C5	0.0388 (11)	0.0315 (13)	0.0401 (14)	−0.0094 (9)	−0.0084 (12)	0.0049 (12)
C6	0.0318 (10)	0.0291 (12)	0.0384 (14)	−0.0052 (9)	−0.0054 (11)	0.0002 (11)
C7	0.0288 (10)	0.0324 (12)	0.0292 (13)	−0.0075 (9)	−0.0007 (10)	0.0017 (10)
C8	0.0268 (10)	0.0343 (12)	0.0324 (12)	−0.0009 (9)	−0.0042 (11)	−0.0024 (10)
C9	0.0385 (11)	0.0578 (16)	0.0366 (17)	−0.0109 (11)	0.0089 (12)	0.0031 (12)
C10	0.0594 (14)	0.0451 (15)	0.0472 (15)	−0.0088 (12)	−0.0102 (16)	0.0129 (14)
C11	0.0396 (12)	0.0361 (13)	0.0513 (17)	0.0052 (10)	−0.0004 (13)	0.0006 (12)
C12	0.0341 (11)	0.0457 (14)	0.0312 (13)	−0.0004 (10)	0.0025 (12)	0.0069 (12)
C13	0.0268 (9)	0.0334 (12)	0.0363 (13)	0.0047 (9)	0.0039 (11)	0.0074 (12)
C14	0.0238 (9)	0.0403 (13)	0.0419 (14)	0.0029 (9)	0.0036 (12)	0.0044 (12)
C15	0.0297 (10)	0.0376 (12)	0.0410 (15)	0.0037 (9)	0.0109 (13)	0.0020 (13)
C16	0.0355 (10)	0.0360 (13)	0.0426 (15)	−0.0007 (9)	0.0038 (12)	−0.0022 (12)
C17	0.0282 (10)	0.0423 (14)	0.0510 (16)	−0.0048 (10)	0.0047 (12)	0.0017 (13)
C18	0.0275 (10)	0.0405 (13)	0.0421 (14)	0.0035 (9)	0.0086 (12)	0.0070 (13)

Cl—C16	1.740 (3)	C9—H9C	0.9600
S—O2	1.4907 (15)	C10—H10A	0.9600
S—C1	1.763 (2)	C10—H10B	0.9600
S—C13	1.791 (3)	C10—H10C	0.9600
O1—C8	1.375 (2)	C11—H11A	0.9600
O1—C7	1.385 (3)	C11—H11B	0.9600
C1—C8	1.352 (3)	C11—H11C	0.9600
C1—C2	1.466 (3)	C12—H12A	0.9600
C2—C7	1.397 (3)	C12—H12B	0.9600
C2—C3	1.402 (3)	C12—H12C	0.9600
C3—C4	1.389 (3)	C13—C14	1.390 (3)
C3—C9	1.508 (3)	C13—C18	1.396 (3)
C4—C5	1.405 (3)	C14—C15	1.377 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.391 (4)	C15—C16	1.376 (3)
C5—C10	1.506 (3)	C15—H15	0.9300
C6—C7	1.379 (3)	C16—C17	1.389 (3)
C6—C11	1.506 (3)	C17—C18	1.373 (4)
C8—C12	1.470 (3)	C17—H17	0.9300
C9—H9A	0.9600	C18—H18	0.9300
C9—H9B	0.9600
O2—S—C1	110.33 (10)	C5—C10—H10B	109.5
O2—S—C13	107.20 (11)	H10A—C10—H10B	109.5
C1—S—C13	98.48 (10)	C5—C10—H10C	109.5
C8—O1—C7	106.57 (16)	H10A—C10—H10C	109.5
C8—C1—C2	107.76 (18)	H10B—C10—H10C	109.5
C8—C1—S	119.19 (18)	C6—C11—H11A	109.5
C2—C1—S	133.01 (17)	C6—C11—H11B	109.5
C7—C2—C3	118.3 (2)	H11A—C11—H11B	109.5
C7—C2—C1	103.78 (19)	C6—C11—H11C	109.5
C3—C2—C1	137.9 (2)	H11A—C11—H11C	109.5
C4—C3—C2	116.1 (2)	H11B—C11—H11C	109.5
C4—C3—C9	120.8 (2)	C8—C12—H12A	109.5
C2—C3—C9	123.1 (2)	C8—C12—H12B	109.5
C3—C4—C5	124.3 (2)	H12A—C12—H12B	109.5
C3—C4—H4	117.9	C8—C12—H12C	109.5
C5—C4—H4	117.9	H12A—C12—H12C	109.5
C6—C5—C4	119.9 (2)	H12B—C12—H12C	109.5
C6—C5—C10	121.0 (2)	C14—C13—C18	120.0 (2)
C4—C5—C10	119.1 (2)	C14—C13—S	119.65 (17)
C7—C6—C5	115.1 (2)	C18—C13—S	120.10 (19)
C7—C6—C11	120.9 (2)	C15—C14—C13	120.4 (2)
C5—C6—C11	124.0 (2)	C15—C14—H14	119.8
C6—C7—O1	122.7 (2)	C13—C14—H14	119.8
C6—C7—C2	126.3 (2)	C16—C15—C14	118.8 (2)
O1—C7—C2	110.98 (19)	C16—C15—H15	120.6
C1—C8—O1	110.9 (2)	C14—C15—H15	120.6
C1—C8—C12	133.7 (2)	C15—C16—C17	121.8 (2)
O1—C8—C12	115.38 (18)	C15—C16—Cl	119.1 (2)
C3—C9—H9A	109.5	C17—C16—Cl	119.11 (17)
C3—C9—H9B	109.5	C18—C17—C16	119.2 (2)
H9A—C9—H9B	109.5	C18—C17—H17	120.4
C3—C9—H9C	109.5	C16—C17—H17	120.4
H9A—C9—H9C	109.5	C17—C18—C13	119.8 (2)
H9B—C9—H9C	109.5	C17—C18—H18	120.1
C5—C10—H10A	109.5	C13—C18—H18	120.1
O2—S—C1—C8	137.63 (18)	C8—O1—C7—C2	0.1 (2)
C13—S—C1—C8	−110.40 (19)	C3—C2—C7—C6	−0.4 (3)
O2—S—C1—C2	−44.6 (3)	C1—C2—C7—C6	−179.7 (2)
C13—S—C1—C2	67.3 (2)	C3—C2—C7—O1	−179.92 (18)
C8—C1—C2—C7	−1.4 (2)	C1—C2—C7—O1	0.7 (2)
S—C1—C2—C7	−179.29 (18)	C2—C1—C8—O1	1.5 (2)
C8—C1—C2—C3	179.5 (3)	S—C1—C8—O1	179.78 (14)
S—C1—C2—C3	1.6 (4)	C2—C1—C8—C12	−175.5 (2)
C7—C2—C3—C4	1.6 (3)	S—C1—C8—C12	2.8 (4)
C1—C2—C3—C4	−179.4 (2)	C7—O1—C8—C1	−1.1 (2)
C7—C2—C3—C9	−179.6 (2)	C7—O1—C8—C12	176.55 (19)
C1—C2—C3—C9	−0.5 (4)	O2—S—C13—C14	−13.4 (2)
C2—C3—C4—C5	−1.3 (4)	C1—S—C13—C14	−127.83 (19)
C9—C3—C4—C5	179.8 (2)	O2—S—C13—C18	172.49 (18)
C3—C4—C5—C6	−0.2 (4)	C1—S—C13—C18	58.0 (2)
C3—C4—C5—C10	178.6 (2)	C18—C13—C14—C15	−1.9 (3)
C4—C5—C6—C7	1.4 (3)	S—C13—C14—C15	−176.00 (19)
C10—C5—C6—C7	−177.4 (2)	C13—C14—C15—C16	1.4 (4)
C4—C5—C6—C11	−179.2 (2)	C14—C15—C16—C17	−0.1 (4)
C10—C5—C6—C11	2.0 (3)	C14—C15—C16—Cl	−179.48 (19)
C5—C6—C7—O1	178.34 (19)	C15—C16—C17—C18	−0.8 (4)
C11—C6—C7—O1	−1.1 (3)	Cl—C16—C17—C18	178.60 (19)
C5—C6—C7—C2	−1.1 (3)	C16—C17—C18—C13	0.3 (4)
C11—C6—C7—C2	179.4 (2)	C14—C13—C18—C17	1.0 (3)
C8—O1—C7—C6	−179.4 (2)	S—C13—C18—C17	175.08 (18)

Cg1 and Cg2 are the centroids of the C13–C18 4-chlorophenyl ring and the C2–C7 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cg1i	0.96	2.76	3.613 (3)	148
C12—H12B···Cg2ii	0.96	2.83	3.653 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13–C18 4-chloro­phenyl ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg1i	0.96	2.76	3.613 (3)	148
C12—H12B⋯Cg2ii	0.96	2.83	3.653 (3)	144

Symmetry codes: (i) ; (ii) .