3-(4-Chloro-phenyl-sulfin-yl)-2,4,6-trimethyl-1-benzofuran.

In the title mol-ecule, C(17)H(15)ClO(2)S, the 4-chloro-phenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 88.98 (4)°]. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O and C-H⋯π inter-actions, forming right-hand pseudo-helices along the a axis.

Related literature

For the structures of related benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products containing benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶).

Experimental

Crystal data

C17H15ClO2S

M = 318.80

Orthorhombic,

a = 12.1259 (10) Å

b = 19.3925 (16) Å

c = 6.4744 (5) Å

V = 1522.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 296 K

0.44 × 0.28 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.848, T max = 0.937

14409 measured reflections

3468 independent reflections

3134 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.03

3468 reflections

194 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1561 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/S1600536810038419/pv2330sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038419/pv2330Isup2.hkl

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

C17H15ClO2S	F(000) = 664
Mr = 318.80	Dx = 1.391 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5206 reflections
a = 12.1259 (10) Å	θ = 2.7–26.9°
b = 19.3925 (16) Å	µ = 0.39 mm−1
c = 6.4744 (5) Å	T = 296 K
V = 1522.5 (2) Å3	Block, colourless
Z = 4	0.44 × 0.28 × 0.17 mm

Bruker SMART APEXII CCD diffractometer	3468 independent reflections
Radiation source: rotating anode	3134 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −25→25
Tmin = 0.848, Tmax = 0.937	l = −8→8
14409 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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1747P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3468 reflections	Δρmax = 0.16 e Å−3
194 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1561 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (6)

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
S	0.58821 (4)	0.24616 (2)	0.00652 (10)	0.04345 (12)
Cl	0.49572 (6)	0.44910 (4)	0.73907 (14)	0.0840 (2)
O1	0.32383 (10)	0.13450 (6)	−0.0716 (2)	0.0445 (3)
O2	0.69629 (11)	0.21294 (7)	0.0504 (3)	0.0574 (4)
C1	0.48058 (14)	0.18533 (8)	0.0312 (3)	0.0377 (4)
C2	0.45571 (14)	0.13178 (8)	0.1815 (3)	0.0373 (4)
C3	0.50175 (15)	0.10563 (9)	0.3645 (3)	0.0418 (4)
C4	0.44487 (17)	0.05245 (10)	0.4608 (3)	0.0483 (5)
H4	0.4739	0.0343	0.5821	0.058*
C5	0.34541 (15)	0.02446 (10)	0.3847 (4)	0.0503 (5)
C6	0.30164 (16)	0.04966 (9)	0.2031 (4)	0.0478 (5)
H6	0.2369	0.0319	0.1473	0.057*
C7	0.35838 (16)	0.10246 (9)	0.1083 (3)	0.0400 (4)
C8	0.40014 (15)	0.18465 (9)	−0.1136 (3)	0.0405 (4)
C9	0.60623 (18)	0.13287 (11)	0.4595 (3)	0.0535 (5)
H9A	0.5897	0.1728	0.5416	0.080*
H9B	0.6571	0.1453	0.3521	0.080*
H9C	0.6386	0.0979	0.5452	0.080*
C10	0.2873 (2)	−0.03139 (12)	0.5061 (6)	0.0758 (7)
H10A	0.2113	−0.0334	0.4652	0.114*
H10B	0.2919	−0.0212	0.6509	0.114*
H10C	0.3219	−0.0750	0.4792	0.114*
C11	0.37730 (19)	0.22734 (11)	−0.2970 (4)	0.0509 (5)
H11A	0.3126	0.2547	−0.2729	0.076*
H11B	0.3654	0.1980	−0.4144	0.076*
H11C	0.4390	0.2571	−0.3232	0.076*
C12	0.55633 (14)	0.30025 (8)	0.2240 (3)	0.0390 (4)
C13	0.45411 (16)	0.33225 (10)	0.2400 (4)	0.0485 (5)
H13	0.3986	0.3226	0.1453	0.058*
C14	0.43614 (17)	0.37853 (10)	0.3984 (4)	0.0522 (5)
H14	0.3684	0.4006	0.4111	0.063*
C15	0.51924 (18)	0.39180 (9)	0.5371 (4)	0.0491 (5)
C16	0.62023 (17)	0.36065 (9)	0.5241 (4)	0.0497 (4)
H16	0.6748	0.3699	0.6211	0.060*
C17	0.63960 (16)	0.31487 (10)	0.3627 (4)	0.0464 (5)
H17	0.7084	0.2942	0.3483	0.056*

	U11	U22	U33	U12	U13	U23
S	0.0401 (2)	0.0491 (2)	0.0411 (2)	−0.00916 (18)	0.0045 (2)	0.0011 (2)
Cl	0.0895 (5)	0.0805 (4)	0.0819 (5)	0.0023 (4)	0.0111 (4)	−0.0341 (4)
O1	0.0401 (7)	0.0475 (7)	0.0461 (8)	−0.0058 (5)	−0.0063 (6)	0.0037 (6)
O2	0.0389 (7)	0.0638 (8)	0.0695 (11)	−0.0017 (6)	0.0088 (7)	−0.0075 (8)
C1	0.0372 (8)	0.0412 (8)	0.0347 (9)	−0.0036 (6)	0.0007 (8)	−0.0015 (7)
C2	0.0358 (9)	0.0383 (8)	0.0377 (9)	0.0011 (7)	0.0055 (8)	−0.0016 (7)
C3	0.0408 (9)	0.0443 (9)	0.0403 (10)	0.0061 (7)	0.0006 (8)	−0.0016 (8)
C4	0.0461 (10)	0.0503 (10)	0.0485 (12)	0.0094 (8)	0.0031 (9)	0.0120 (8)
C5	0.0449 (11)	0.0427 (9)	0.0632 (14)	0.0044 (7)	0.0116 (10)	0.0114 (9)
C6	0.0366 (9)	0.0418 (8)	0.0649 (14)	−0.0034 (7)	0.0024 (9)	0.0049 (9)
C7	0.0381 (9)	0.0405 (8)	0.0416 (10)	0.0022 (7)	0.0013 (8)	0.0001 (8)
C8	0.0407 (9)	0.0428 (9)	0.0380 (10)	−0.0026 (7)	0.0010 (8)	−0.0006 (7)
C9	0.0506 (12)	0.0615 (12)	0.0485 (14)	0.0018 (9)	−0.0076 (10)	0.0025 (9)
C10	0.0633 (14)	0.0679 (13)	0.096 (2)	−0.0044 (11)	0.0056 (16)	0.0395 (15)
C11	0.0522 (11)	0.0588 (11)	0.0416 (11)	−0.0017 (10)	−0.0031 (9)	0.0068 (9)
C12	0.0379 (9)	0.0373 (8)	0.0417 (10)	−0.0054 (7)	−0.0014 (8)	0.0037 (8)
C13	0.0431 (10)	0.0481 (10)	0.0542 (12)	−0.0012 (8)	−0.0102 (10)	0.0042 (9)
C14	0.0441 (10)	0.0460 (10)	0.0666 (14)	0.0061 (8)	−0.0001 (10)	0.0011 (10)
C15	0.0583 (12)	0.0382 (9)	0.0508 (12)	−0.0032 (8)	0.0049 (10)	−0.0034 (9)
C16	0.0481 (10)	0.0501 (10)	0.0509 (12)	−0.0060 (8)	−0.0088 (11)	−0.0027 (10)
C17	0.0358 (9)	0.0481 (9)	0.0553 (13)	−0.0030 (8)	−0.0046 (9)	−0.0018 (9)

S—O2	1.4878 (15)	C9—H9A	0.9600
S—C1	1.7665 (17)	C9—H9B	0.9600
S—C12	1.798 (2)	C9—H9C	0.9600
Cl—C15	1.740 (2)	C10—H10A	0.9600
O1—C8	1.370 (2)	C10—H10B	0.9600
O1—C7	1.385 (2)	C10—H10C	0.9600
C1—C8	1.353 (3)	C11—H11A	0.9600
C1—C2	1.455 (2)	C11—H11B	0.9600
C2—C7	1.393 (3)	C11—H11C	0.9600
C2—C3	1.405 (3)	C12—C17	1.381 (3)
C3—C4	1.389 (3)	C12—C13	1.390 (3)
C3—C9	1.504 (3)	C13—C14	1.380 (3)
C4—C5	1.411 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.374 (3)
C5—C6	1.379 (3)	C14—H14	0.9300
C5—C10	1.512 (3)	C15—C16	1.368 (3)
C6—C7	1.378 (3)	C16—C17	1.391 (3)
C6—H6	0.9300	C16—H16	0.9300
C8—C11	1.474 (3)	C17—H17	0.9300
O2—S—C1	110.14 (8)	H9A—C9—H9C	109.5
O2—S—C12	107.01 (9)	H9B—C9—H9C	109.5
C1—S—C12	99.20 (8)	C5—C10—H10A	109.5
C8—O1—C7	106.32 (15)	C5—C10—H10B	109.5
C8—C1—C2	107.89 (15)	H10A—C10—H10B	109.5
C8—C1—S	118.45 (14)	C5—C10—H10C	109.5
C2—C1—S	133.66 (14)	H10A—C10—H10C	109.5
C7—C2—C3	118.46 (16)	H10B—C10—H10C	109.5
C7—C2—C1	103.84 (16)	C8—C11—H11A	109.5
C3—C2—C1	137.70 (17)	C8—C11—H11B	109.5
C4—C3—C2	116.71 (17)	H11A—C11—H11B	109.5
C4—C3—C9	119.73 (19)	C8—C11—H11C	109.5
C2—C3—C9	123.55 (18)	H11A—C11—H11C	109.5
C3—C4—C5	123.59 (19)	H11B—C11—H11C	109.5
C3—C4—H4	118.2	C17—C12—C13	120.78 (18)
C5—C4—H4	118.2	C17—C12—S	118.16 (14)
C6—C5—C4	119.37 (18)	C13—C12—S	120.72 (15)
C6—C5—C10	121.2 (2)	C14—C13—C12	119.13 (19)
C4—C5—C10	119.5 (2)	C14—C13—H13	120.4
C7—C6—C5	116.80 (19)	C12—C13—H13	120.4
C7—C6—H6	121.6	C15—C14—C13	119.45 (18)
C5—C6—H6	121.6	C15—C14—H14	120.3
C6—C7—O1	123.85 (18)	C13—C14—H14	120.3
C6—C7—C2	125.07 (18)	C16—C15—C14	122.23 (19)
O1—C7—C2	111.06 (15)	C16—C15—Cl	118.38 (18)
C1—C8—O1	110.88 (17)	C14—C15—Cl	119.39 (16)
C1—C8—C11	133.50 (17)	C15—C16—C17	118.6 (2)
O1—C8—C11	115.58 (16)	C15—C16—H16	120.7
C3—C9—H9A	109.5	C17—C16—H16	120.7
C3—C9—H9B	109.5	C12—C17—C16	119.75 (18)
H9A—C9—H9B	109.5	C12—C17—H17	120.1
C3—C9—H9C	109.5	C16—C17—H17	120.1
O2—S—C1—C8	−136.54 (15)	C1—C2—C7—C6	−178.86 (18)
C12—S—C1—C8	111.43 (16)	C3—C2—C7—O1	179.46 (15)
O2—S—C1—C2	43.6 (2)	C1—C2—C7—O1	−0.29 (19)
C12—S—C1—C2	−68.45 (18)	C2—C1—C8—O1	−0.3 (2)
C8—C1—C2—C7	0.3 (2)	S—C1—C8—O1	179.82 (13)
S—C1—C2—C7	−179.78 (15)	C2—C1—C8—C11	177.3 (2)
C8—C1—C2—C3	−179.3 (2)	S—C1—C8—C11	−2.6 (3)
S—C1—C2—C3	0.6 (3)	C7—O1—C8—C1	0.1 (2)
C7—C2—C3—C4	−0.9 (3)	C7—O1—C8—C11	−177.95 (16)
C1—C2—C3—C4	178.8 (2)	O2—S—C12—C17	14.13 (17)
C7—C2—C3—C9	−179.91 (18)	C1—S—C12—C17	128.60 (15)
C1—C2—C3—C9	−0.3 (3)	O2—S—C12—C13	−172.53 (15)
C2—C3—C4—C5	−0.1 (3)	C1—S—C12—C13	−58.05 (16)
C9—C3—C4—C5	178.97 (19)	C17—C12—C13—C14	−0.7 (3)
C3—C4—C5—C6	1.1 (3)	S—C12—C13—C14	−173.88 (15)
C3—C4—C5—C10	−177.4 (2)	C12—C13—C14—C15	−0.3 (3)
C4—C5—C6—C7	−1.1 (3)	C13—C14—C15—C16	0.1 (3)
C10—C5—C6—C7	177.4 (2)	C13—C14—C15—Cl	−178.98 (17)
C5—C6—C7—O1	−178.26 (17)	C14—C15—C16—C17	1.0 (3)
C5—C6—C7—C2	0.1 (3)	Cl—C15—C16—C17	−179.89 (16)
C8—O1—C7—C6	178.73 (19)	C13—C12—C17—C16	1.8 (3)
C8—O1—C7—C2	0.14 (19)	S—C12—C17—C16	175.18 (16)
C3—C2—C7—C6	0.9 (3)	C15—C16—C17—C12	−2.0 (3)

Cg is the centroid of the C12–C17 4-chlorophenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2i	0.93	2.62	3.471 (2)	152
C11—H11C···Cgii	0.96	2.85	3.667 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 4-chloro­phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2i	0.93	2.62	3.471 (2)	152
C11—H11C⋯Cgii	0.96	2.85	3.667 (2)	144

Symmetry codes: (i) ; (ii) .