2-(4-Chloro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

In the title compound, C(21)H(15)ClOS, the 4-chloro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 21.50 (6)°. The dihedral angle between the 5-phenyl ring and the benzofuran plane is 29.39 (6)°. The crystal studied was an inversion twin with a 0.65 (7):0.35 (6) domain ratio.

Related literature

For the crystal structures of similar benzofuran derivatives, see: Choi, et al. (2009 ▶, 2010 ▶). For the pharmacological 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 ▶).

Experimental

Crystal data

C21H15ClOS

M = 350.84

Monoclinic,

a = 10.921 (1) Å

b = 7.2225 (8) Å

c = 11.740 (1) Å

β = 115.132 (6)°

V = 838.35 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 173 K

0.27 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.911, T max = 0.951

7754 measured reflections

3571 independent reflections

3376 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.05

3571 reflections

219 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1505 Friedel pairs

Flack parameter: 0.35 (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/S1600536810008706/fl2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008706/fl2295Isup2.hkl

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

C21H15ClOS	F(000) = 364
Mr = 350.84	Dx = 1.390 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4886 reflections
a = 10.921 (1) Å	θ = 3.4–27.4°
b = 7.2225 (8) Å	µ = 0.36 mm−1
c = 11.740 (1) Å	T = 173 K
β = 115.132 (6)°	Block, colourless
V = 838.35 (14) Å3	0.27 × 0.15 × 0.14 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	3571 independent reflections
Radiation source: Rotating Anode	3376 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.4°, θmin = 1.9°
φ and ω scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→8
Tmin = 0.911, Tmax = 0.951	l = −15→15
7754 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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.051P)2 + 0.0803P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3571 reflections	Δρmax = 0.28 e Å−3
219 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 1505 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.35 (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
Cl	−0.26159 (5)	0.53997 (9)	−0.01679 (5)	0.04418 (14)
S	0.45654 (5)	0.50246 (9)	0.13481 (4)	0.04300 (16)
O	0.37078 (12)	0.5417 (2)	0.43085 (10)	0.0297 (3)
C1	0.44798 (18)	0.5179 (3)	0.28020 (15)	0.0289 (4)
C2	0.56317 (17)	0.5235 (3)	0.40109 (15)	0.0267 (3)
C3	0.70372 (18)	0.5202 (3)	0.44147 (15)	0.0276 (4)
H3	0.7412	0.5078	0.3822	0.033*
C4	0.78803 (17)	0.5353 (3)	0.56955 (15)	0.0270 (3)
C5	0.72841 (19)	0.5488 (3)	0.65544 (16)	0.0311 (4)
H5	0.7859	0.5565	0.7428	0.037*
C6	0.58971 (19)	0.5512 (3)	0.61716 (16)	0.0321 (4)
H6	0.5513	0.5607	0.6759	0.039*
C7	0.51007 (18)	0.5391 (3)	0.48929 (15)	0.0287 (3)
C8	0.33570 (18)	0.5302 (3)	0.30249 (15)	0.0286 (4)
C9	0.19012 (18)	0.5351 (3)	0.22349 (15)	0.0281 (3)
C10	0.1017 (2)	0.6099 (3)	0.26900 (18)	0.0297 (4)
H10	0.1372	0.6584	0.3520	0.036*
C11	−0.0366 (2)	0.6149 (3)	0.19605 (19)	0.0329 (4)
H11	−0.0955	0.6672	0.2281	0.039*
C12	−0.08758 (18)	0.5422 (3)	0.07541 (16)	0.0304 (4)
C13	−0.0032 (2)	0.4675 (3)	0.02688 (17)	0.0335 (4)
H13	−0.0399	0.4188	−0.0561	0.040*
C14	0.1356 (2)	0.4641 (3)	0.10026 (18)	0.0325 (4)
H14	0.1939	0.4135	0.0670	0.039*
C15	0.93761 (17)	0.5412 (3)	0.61447 (15)	0.0271 (3)
C16	1.0017 (2)	0.4543 (3)	0.54744 (18)	0.0316 (4)
H16	0.9492	0.3851	0.4739	0.038*
C17	1.1406 (2)	0.4677 (3)	0.58677 (19)	0.0364 (4)
H17	1.1821	0.4085	0.5399	0.044*
C18	1.2186 (2)	0.5668 (3)	0.6939 (2)	0.0413 (5)
H18	1.3134	0.5781	0.7198	0.050*
C19	1.1582 (2)	0.6494 (3)	0.7630 (2)	0.0416 (5)
H19	1.2119	0.7152	0.8377	0.050*
C20	1.0191 (2)	0.6369 (3)	0.72411 (19)	0.0337 (4)
H20	0.9789	0.6941	0.7727	0.040*
C21	0.5393 (3)	0.7197 (4)	0.1356 (2)	0.0511 (6)
H21A	0.6327	0.7160	0.2004	0.077*
H21B	0.4906	0.8211	0.1538	0.077*
H21C	0.5394	0.7398	0.0531	0.077*

	U11	U22	U33	U12	U13	U23
Cl	0.0278 (2)	0.0580 (3)	0.0424 (3)	0.0004 (3)	0.0107 (2)	0.0047 (3)
S	0.0401 (3)	0.0664 (4)	0.0278 (2)	−0.0108 (3)	0.0195 (2)	−0.0125 (2)
O	0.0273 (6)	0.0387 (7)	0.0259 (5)	−0.0008 (7)	0.0140 (5)	−0.0006 (6)
C1	0.0306 (9)	0.0330 (10)	0.0255 (7)	−0.0046 (8)	0.0142 (7)	−0.0049 (8)
C2	0.0298 (8)	0.0270 (9)	0.0251 (7)	−0.0008 (8)	0.0133 (7)	−0.0007 (8)
C3	0.0325 (9)	0.0265 (9)	0.0270 (7)	−0.0005 (8)	0.0158 (7)	0.0003 (8)
C4	0.0302 (8)	0.0237 (8)	0.0280 (8)	0.0014 (8)	0.0132 (7)	−0.0003 (8)
C5	0.0348 (9)	0.0347 (9)	0.0232 (7)	0.0019 (9)	0.0116 (7)	0.0025 (8)
C6	0.0352 (9)	0.0388 (10)	0.0273 (8)	0.0014 (9)	0.0178 (7)	0.0003 (9)
C7	0.0297 (8)	0.0301 (9)	0.0289 (8)	−0.0003 (9)	0.0150 (7)	0.0007 (9)
C8	0.0337 (9)	0.0278 (8)	0.0253 (7)	−0.0021 (9)	0.0134 (7)	−0.0033 (8)
C9	0.0307 (8)	0.0243 (8)	0.0305 (8)	−0.0030 (9)	0.0143 (7)	−0.0003 (8)
C10	0.0329 (10)	0.0291 (9)	0.0293 (9)	−0.0030 (8)	0.0152 (8)	−0.0034 (7)
C11	0.0324 (10)	0.0318 (9)	0.0402 (10)	0.0008 (8)	0.0209 (9)	−0.0011 (8)
C12	0.0267 (8)	0.0294 (9)	0.0321 (8)	−0.0011 (9)	0.0096 (7)	0.0049 (9)
C13	0.0336 (10)	0.0366 (10)	0.0272 (8)	0.0008 (9)	0.0099 (8)	−0.0011 (8)
C14	0.0320 (10)	0.0348 (10)	0.0321 (9)	0.0005 (8)	0.0148 (8)	−0.0034 (8)
C15	0.0306 (8)	0.0239 (8)	0.0264 (7)	0.0026 (9)	0.0118 (7)	0.0045 (8)
C16	0.0327 (10)	0.0310 (10)	0.0311 (9)	0.0025 (8)	0.0135 (8)	0.0004 (8)
C17	0.0357 (11)	0.0349 (10)	0.0428 (10)	0.0080 (9)	0.0206 (9)	0.0025 (9)
C18	0.0279 (9)	0.0415 (13)	0.0511 (12)	0.0045 (9)	0.0135 (9)	0.0003 (10)
C19	0.0337 (11)	0.0396 (12)	0.0404 (11)	0.0017 (9)	0.0050 (9)	−0.0066 (9)
C20	0.0324 (10)	0.0334 (10)	0.0328 (10)	0.0045 (9)	0.0113 (8)	−0.0030 (8)
C21	0.0511 (15)	0.0618 (15)	0.0523 (14)	0.0084 (12)	0.0334 (13)	0.0191 (12)

Cl—C12	1.7425 (18)	C10—H10	0.9500
S—C1	1.7523 (15)	C11—C12	1.386 (3)
S—C21	1.809 (3)	C11—H11	0.9500
O—C7	1.378 (2)	C12—C13	1.382 (3)
O—C8	1.3907 (18)	C13—C14	1.390 (3)
C1—C8	1.361 (2)	C13—H13	0.9500
C1—C2	1.443 (2)	C14—H14	0.9500
C2—C7	1.390 (2)	C15—C20	1.397 (3)
C2—C3	1.401 (2)	C15—C16	1.404 (2)
C3—C4	1.394 (2)	C16—C17	1.388 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.417 (2)	C17—C18	1.382 (3)
C4—C15	1.489 (2)	C17—H17	0.9500
C5—C6	1.385 (3)	C18—C19	1.381 (3)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.382 (2)	C19—C20	1.391 (3)
C6—H6	0.9500	C19—H19	0.9500
C8—C9	1.462 (2)	C20—H20	0.9500
C9—C10	1.396 (3)	C21—H21A	0.9800
C9—C14	1.407 (2)	C21—H21B	0.9800
C10—C11	1.384 (3)	C21—H21C	0.9800
C1—S—C21	99.95 (11)	C12—C11—H11	120.6
C7—O—C8	106.06 (12)	C13—C12—C11	121.37 (17)
C8—C1—C2	106.82 (14)	C13—C12—Cl	118.84 (14)
C8—C1—S	128.07 (14)	C11—C12—Cl	119.78 (14)
C2—C1—S	125.10 (13)	C12—C13—C14	119.59 (17)
C7—C2—C3	119.55 (15)	C12—C13—H13	120.2
C7—C2—C1	105.65 (15)	C14—C13—H13	120.2
C3—C2—C1	134.79 (14)	C13—C14—C9	120.33 (17)
C4—C3—C2	119.35 (14)	C13—C14—H14	119.8
C4—C3—H3	120.3	C9—C14—H14	119.8
C2—C3—H3	120.3	C20—C15—C16	117.61 (17)
C3—C4—C5	118.70 (16)	C20—C15—C4	120.92 (16)
C3—C4—C15	120.45 (14)	C16—C15—C4	121.46 (16)
C5—C4—C15	120.84 (15)	C17—C16—C15	121.11 (18)
C6—C5—C4	122.67 (16)	C17—C16—H16	119.4
C6—C5—H5	118.7	C15—C16—H16	119.4
C4—C5—H5	118.7	C18—C17—C16	120.21 (18)
C7—C6—C5	116.66 (15)	C18—C17—H17	119.9
C7—C6—H6	121.7	C16—C17—H17	119.9
C5—C6—H6	121.7	C19—C18—C17	119.66 (19)
O—C7—C6	126.34 (14)	C19—C18—H18	120.2
O—C7—C2	110.60 (14)	C17—C18—H18	120.2
C6—C7—C2	123.06 (16)	C18—C19—C20	120.46 (19)
C1—C8—O	110.86 (15)	C18—C19—H19	119.8
C1—C8—C9	134.88 (15)	C20—C19—H19	119.8
O—C8—C9	114.26 (14)	C19—C20—C15	120.92 (18)
C10—C9—C14	118.36 (17)	C19—C20—H20	119.5
C10—C9—C8	120.64 (15)	C15—C20—H20	119.5
C14—C9—C8	121.00 (16)	S—C21—H21A	109.5
C11—C10—C9	121.59 (16)	S—C21—H21B	109.5
C11—C10—H10	119.2	H21A—C21—H21B	109.5
C9—C10—H10	119.2	S—C21—H21C	109.5
C10—C11—C12	118.75 (17)	H21A—C21—H21C	109.5
C10—C11—H11	120.6	H21B—C21—H21C	109.5
C21—S—C1—C8	114.7 (2)	C1—C8—C9—C10	−158.1 (2)
C21—S—C1—C2	−63.9 (2)	O—C8—C9—C10	21.4 (3)
C8—C1—C2—C7	0.1 (2)	C1—C8—C9—C14	22.2 (4)
S—C1—C2—C7	178.95 (16)	O—C8—C9—C14	−158.26 (19)
C8—C1—C2—C3	−178.6 (2)	C14—C9—C10—C11	0.1 (3)
S—C1—C2—C3	0.3 (4)	C8—C9—C10—C11	−179.60 (18)
C7—C2—C3—C4	−0.9 (3)	C9—C10—C11—C12	0.6 (3)
C1—C2—C3—C4	177.6 (2)	C10—C11—C12—C13	−0.8 (3)
C2—C3—C4—C5	1.6 (3)	C10—C11—C12—Cl	178.00 (16)
C2—C3—C4—C15	−177.07 (18)	C11—C12—C13—C14	0.3 (3)
C3—C4—C5—C6	−1.3 (3)	Cl—C12—C13—C14	−178.46 (15)
C15—C4—C5—C6	177.4 (2)	C12—C13—C14—C9	0.3 (3)
C4—C5—C6—C7	0.2 (3)	C10—C9—C14—C13	−0.5 (3)
C8—O—C7—C6	178.7 (2)	C8—C9—C14—C13	179.14 (18)
C8—O—C7—C2	−0.9 (2)	C3—C4—C15—C20	150.24 (19)
C5—C6—C7—O	−179.0 (2)	C5—C4—C15—C20	−28.4 (3)
C5—C6—C7—C2	0.5 (3)	C3—C4—C15—C16	−28.6 (3)
C3—C2—C7—O	179.40 (17)	C5—C4—C15—C16	152.8 (2)
C1—C2—C7—O	0.5 (2)	C20—C15—C16—C17	−1.9 (3)
C3—C2—C7—C6	−0.2 (3)	C4—C15—C16—C17	176.97 (18)
C1—C2—C7—C6	−179.1 (2)	C15—C16—C17—C18	0.4 (3)
C2—C1—C8—O	−0.6 (3)	C16—C17—C18—C19	1.3 (3)
S—C1—C8—O	−179.45 (15)	C17—C18—C19—C20	−1.4 (3)
C2—C1—C8—C9	178.9 (2)	C18—C19—C20—C15	−0.2 (3)
S—C1—C8—C9	0.1 (4)	C16—C15—C20—C19	1.8 (3)
C7—O—C8—C1	0.9 (2)	C4—C15—C20—C19	−177.09 (19)
C7—O—C8—C9	−178.73 (16)