5-Chloro-7-methyl-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(21)H(15)ClO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the phenyl ring is almost perpendicular to this plane [82.24 (7)°]. The phenyl ring in the 2-position is rotated out of the benzofuran plane, making a dihedral angle of 11.50 (9)°. The crystal structure is stabilized by inter-molecular C-H⋯O and C-H⋯Cl inter-actions. In addition, the stacked mol-ecules exhibit an inter-molecular S⋯O inter-action [3.327 (2) Å] involving the sulfinyl groups.

Related literature

For the crystal structures of similar 5-chloro-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2008a ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008b ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C21H15ClO2S

M = 366.84

Triclinic,

a = 8.224 (1) Å

b = 10.169 (1) Å

c = 11.083 (2) Å

α = 68.771 (2)°

β = 78.050 (2)°

γ = 81.483 (2)°

V = 842.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 273 K

0.35 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.910, T max = 0.932

6585 measured reflections

3270 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.06

3270 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536809024763/ng2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024763/ng2607Isup2.hkl

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

C21H15ClO2S	Z = 2
Mr = 366.84	F(000) = 380
Triclinic, P1	Dx = 1.446 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.224 (1) Å	Cell parameters from 3597 reflections
b = 10.169 (1) Å	θ = 2.4–27.4°
c = 11.083 (2) Å	µ = 0.36 mm−1
α = 68.771 (2)°	T = 273 K
β = 78.050 (2)°	Block, colourless
γ = 81.483 (2)°	0.35 × 0.20 × 0.20 mm
V = 842.5 (2) Å3

Bruker SMART CCD diffractometer	3270 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
Tmin = 0.910, Tmax = 0.932	l = −13→13
6585 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) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.2839P] where P = (Fo2 + 2Fc2)/3
3270 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.45 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
Cl	−0.03805 (7)	0.27602 (6)	−0.01980 (6)	0.04107 (17)
S	0.16845 (6)	0.39221 (5)	0.42629 (5)	0.02979 (16)
O1	0.23043 (17)	−0.01506 (14)	0.46155 (13)	0.0285 (3)
O2	0.04121 (18)	0.47817 (16)	0.34509 (18)	0.0435 (4)
C1	0.1811 (2)	0.2199 (2)	0.4171 (2)	0.0264 (4)
C2	0.1373 (2)	0.1876 (2)	0.3117 (2)	0.0267 (4)
C3	0.0730 (2)	0.2646 (2)	0.1967 (2)	0.0305 (5)
H3	0.0487	0.3621	0.1712	0.037*
C4	0.0477 (2)	0.1874 (2)	0.1228 (2)	0.0306 (5)
C5	0.0854 (2)	0.0415 (2)	0.1569 (2)	0.0310 (5)
H5	0.0673	−0.0043	0.1024	0.037*
C6	0.1494 (2)	−0.0362 (2)	0.2703 (2)	0.0288 (4)
C7	0.1711 (2)	0.0418 (2)	0.3446 (2)	0.0274 (4)
C8	0.2345 (2)	0.0952 (2)	0.5053 (2)	0.0276 (4)
C9	0.2953 (2)	0.0527 (2)	0.6299 (2)	0.0279 (4)
C10	0.2804 (3)	0.1420 (2)	0.7028 (2)	0.0359 (5)
H10	0.2325	0.2341	0.6711	0.043*
C11	0.3366 (3)	0.0941 (3)	0.8220 (2)	0.0405 (5)
H11	0.3266	0.1544	0.8697	0.049*
C12	0.4074 (3)	−0.0426 (3)	0.8707 (2)	0.0428 (6)
H12	0.4440	−0.0746	0.9513	0.051*
C13	0.4234 (3)	−0.1312 (3)	0.7991 (2)	0.0434 (6)
H13	0.4721	−0.2229	0.8310	0.052*
C14	0.3674 (3)	−0.0846 (2)	0.6801 (2)	0.0359 (5)
H14	0.3779	−0.1457	0.6331	0.043*
C15	0.1942 (3)	−0.1933 (2)	0.3103 (2)	0.0375 (5)
H15A	0.1356	−0.2332	0.2670	0.056*
H15B	0.1635	−0.2360	0.4036	0.056*
H15C	0.3121	−0.2110	0.2857	0.056*
C16	0.3687 (2)	0.44102 (19)	0.3307 (2)	0.0255 (4)
C17	0.3857 (3)	0.5151 (2)	0.1978 (2)	0.0384 (5)
H17	0.2941	0.5382	0.1549	0.046*
C18	0.5425 (4)	0.5546 (3)	0.1292 (3)	0.0523 (7)
H18	0.5564	0.6043	0.0394	0.063*
C19	0.6776 (3)	0.5206 (3)	0.1937 (3)	0.0537 (7)
H19	0.7824	0.5467	0.1469	0.064*
C20	0.6586 (3)	0.4486 (3)	0.3261 (3)	0.0479 (6)
H20	0.7501	0.4268	0.3691	0.058*
C21	0.5045 (3)	0.4088 (2)	0.3955 (2)	0.0349 (5)
H21	0.4912	0.3604	0.4855	0.042*

	U11	U22	U33	U12	U13	U23
Cl	0.0383 (3)	0.0419 (3)	0.0439 (3)	−0.0030 (2)	−0.0165 (2)	−0.0105 (3)
S	0.0222 (3)	0.0257 (3)	0.0467 (3)	0.00223 (19)	−0.0041 (2)	−0.0209 (2)
O1	0.0335 (7)	0.0224 (7)	0.0312 (8)	−0.0028 (6)	−0.0043 (6)	−0.0114 (6)
O2	0.0248 (7)	0.0356 (9)	0.0799 (12)	0.0119 (6)	−0.0211 (8)	−0.0301 (9)
C1	0.0217 (9)	0.0231 (10)	0.0367 (11)	−0.0007 (8)	−0.0024 (8)	−0.0147 (9)
C2	0.0215 (9)	0.0251 (10)	0.0358 (11)	−0.0021 (8)	−0.0024 (8)	−0.0146 (9)
C3	0.0241 (10)	0.0258 (10)	0.0424 (12)	−0.0010 (8)	−0.0056 (9)	−0.0131 (9)
C4	0.0238 (10)	0.0329 (11)	0.0340 (11)	−0.0039 (8)	−0.0052 (8)	−0.0095 (9)
C5	0.0286 (10)	0.0333 (11)	0.0350 (11)	−0.0070 (9)	−0.0019 (9)	−0.0162 (9)
C6	0.0273 (10)	0.0271 (10)	0.0346 (11)	−0.0046 (8)	−0.0017 (8)	−0.0144 (9)
C7	0.0242 (10)	0.0282 (10)	0.0306 (11)	−0.0041 (8)	−0.0006 (8)	−0.0123 (8)
C8	0.0242 (10)	0.0257 (10)	0.0359 (11)	−0.0038 (8)	0.0006 (8)	−0.0164 (9)
C9	0.0235 (10)	0.0294 (10)	0.0308 (11)	−0.0051 (8)	0.0020 (8)	−0.0127 (9)
C10	0.0424 (12)	0.0294 (11)	0.0377 (12)	−0.0033 (9)	−0.0037 (10)	−0.0150 (10)
C11	0.0482 (14)	0.0449 (13)	0.0358 (13)	−0.0084 (11)	−0.0051 (10)	−0.0220 (11)
C12	0.0461 (14)	0.0468 (14)	0.0372 (13)	−0.0050 (11)	−0.0118 (11)	−0.0133 (11)
C13	0.0469 (14)	0.0369 (13)	0.0453 (14)	0.0067 (11)	−0.0148 (11)	−0.0129 (11)
C14	0.0379 (12)	0.0332 (12)	0.0401 (13)	0.0020 (9)	−0.0064 (10)	−0.0187 (10)
C15	0.0466 (13)	0.0268 (11)	0.0440 (13)	−0.0032 (10)	−0.0076 (10)	−0.0176 (10)
C16	0.0221 (9)	0.0182 (9)	0.0390 (11)	0.0017 (7)	−0.0069 (8)	−0.0135 (8)
C17	0.0424 (13)	0.0303 (11)	0.0418 (13)	0.0059 (10)	−0.0148 (10)	−0.0109 (10)
C18	0.0673 (18)	0.0342 (13)	0.0413 (15)	−0.0070 (12)	0.0066 (13)	−0.0036 (11)
C19	0.0351 (13)	0.0378 (14)	0.080 (2)	−0.0092 (11)	0.0102 (13)	−0.0188 (14)
C20	0.0264 (11)	0.0413 (13)	0.080 (2)	−0.0023 (10)	−0.0134 (12)	−0.0232 (13)
C21	0.0321 (11)	0.0317 (11)	0.0438 (13)	−0.0012 (9)	−0.0144 (10)	−0.0126 (10)

Cl—C4	1.747 (2)	C10—H10	0.9300
S—O2	1.489 (2)	C11—C12	1.382 (3)
S—O2i	3.327 (2)	C11—H11	0.9300
S—C1	1.778 (2)	C12—C13	1.378 (3)
S—C16	1.794 (2)	C12—H12	0.9300
O1—C7	1.374 (2)	C13—C14	1.382 (3)
O1—C8	1.381 (2)	C13—H13	0.9300
C1—C8	1.368 (3)	C14—H14	0.9300
C1—C2	1.446 (3)	C15—H15A	0.9600
C2—C7	1.391 (3)	C15—H15B	0.9600
C2—C3	1.397 (3)	C15—H15C	0.9600
C3—C4	1.384 (3)	C16—C17	1.378 (3)
C3—H3	0.9300	C16—C21	1.387 (3)
C4—C5	1.396 (3)	C17—C18	1.388 (3)
C5—C6	1.383 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.378 (4)
C6—C7	1.384 (3)	C18—H18	0.9300
C6—C15	1.505 (3)	C19—C20	1.370 (4)
C8—C9	1.460 (3)	C19—H19	0.9300
C9—C14	1.392 (3)	C20—C21	1.372 (3)
C9—C10	1.397 (3)	C20—H20	0.9300
C10—C11	1.384 (3)	C21—H21	0.9300
O2—S—C1	105.84 (9)	C12—C11—H11	119.7
O2—S—C16	106.83 (10)	C10—C11—H11	119.7
C1—S—C16	97.45 (9)	C13—C12—C11	119.5 (2)
C7—O1—C8	107.09 (15)	C13—C12—H12	120.3
C8—C1—C2	107.53 (17)	C11—C12—H12	120.3
C8—C1—S	127.27 (16)	C12—C13—C14	120.4 (2)
C2—C1—S	125.20 (15)	C12—C13—H13	119.8
C7—C2—C3	119.26 (18)	C14—C13—H13	119.8
C7—C2—C1	104.90 (18)	C13—C14—C9	120.8 (2)
C3—C2—C1	135.84 (18)	C13—C14—H14	119.6
C4—C3—C2	116.10 (19)	C9—C14—H14	119.6
C4—C3—H3	122.0	C6—C15—H15A	109.5
C2—C3—H3	122.0	C6—C15—H15B	109.5
C3—C4—C5	123.5 (2)	H15A—C15—H15B	109.5
C3—C4—Cl	118.61 (16)	C6—C15—H15C	109.5
C5—C4—Cl	117.89 (16)	H15A—C15—H15C	109.5
C6—C5—C4	121.07 (19)	H15B—C15—H15C	109.5
C6—C5—H5	119.5	C17—C16—C21	120.8 (2)
C4—C5—H5	119.5	C17—C16—S	120.98 (16)
C5—C6—C7	114.86 (18)	C21—C16—S	118.11 (17)
C5—C6—C15	123.06 (18)	C16—C17—C18	118.7 (2)
C7—C6—C15	122.08 (19)	C16—C17—H17	120.7
O1—C7—C6	124.18 (18)	C18—C17—H17	120.7
O1—C7—C2	110.62 (17)	C19—C18—C17	120.3 (2)
C6—C7—C2	125.2 (2)	C19—C18—H18	119.8
C1—C8—O1	109.86 (17)	C17—C18—H18	119.8
C1—C8—C9	135.94 (18)	C20—C19—C18	120.5 (2)
O1—C8—C9	114.20 (17)	C20—C19—H19	119.8
C14—C9—C10	118.4 (2)	C18—C19—H19	119.8
C14—C9—C8	118.49 (18)	C19—C20—C21	120.0 (2)
C10—C9—C8	123.04 (19)	C19—C20—H20	120.0
C11—C10—C9	120.3 (2)	C21—C20—H20	120.0
C11—C10—H10	119.9	C20—C21—C16	119.7 (2)
C9—C10—H10	119.9	C20—C21—H21	120.1
C12—C11—C10	120.6 (2)	C16—C21—H21	120.1
O2—S—C1—C8	−156.31 (18)	C2—C1—C8—C9	179.9 (2)
C16—S—C1—C8	93.77 (19)	S—C1—C8—C9	0.6 (4)
O2—S—C1—C2	24.43 (19)	C7—O1—C8—C1	−0.8 (2)
C16—S—C1—C2	−85.48 (18)	C7—O1—C8—C9	−179.96 (15)
C8—C1—C2—C7	−0.9 (2)	C1—C8—C9—C14	−168.4 (2)
S—C1—C2—C7	178.49 (14)	O1—C8—C9—C14	10.4 (3)
C8—C1—C2—C3	178.3 (2)	C1—C8—C9—C10	13.4 (4)
S—C1—C2—C3	−2.3 (3)	O1—C8—C9—C10	−167.76 (18)
C7—C2—C3—C4	0.0 (3)	C14—C9—C10—C11	0.1 (3)
C1—C2—C3—C4	−179.1 (2)	C8—C9—C10—C11	178.25 (19)
C2—C3—C4—C5	−1.1 (3)	C9—C10—C11—C12	−0.3 (3)
C2—C3—C4—Cl	178.18 (14)	C10—C11—C12—C13	0.6 (4)
C3—C4—C5—C6	1.1 (3)	C11—C12—C13—C14	−0.8 (4)
Cl—C4—C5—C6	−178.25 (15)	C12—C13—C14—C9	0.6 (4)
C4—C5—C6—C7	0.2 (3)	C10—C9—C14—C13	−0.2 (3)
C4—C5—C6—C15	−179.2 (2)	C8—C9—C14—C13	−178.5 (2)
C8—O1—C7—C6	179.90 (18)	O2—S—C16—C17	−15.11 (19)
C8—O1—C7—C2	0.3 (2)	C1—S—C16—C17	93.99 (18)
C5—C6—C7—O1	178.93 (17)	O2—S—C16—C21	161.49 (15)
C15—C6—C7—O1	−1.7 (3)	C1—S—C16—C21	−89.42 (17)
C5—C6—C7—C2	−1.5 (3)	C21—C16—C17—C18	1.2 (3)
C15—C6—C7—C2	177.9 (2)	S—C16—C17—C18	177.74 (17)
C3—C2—C7—O1	−178.94 (16)	C16—C17—C18—C19	−0.3 (4)
C1—C2—C7—O1	0.4 (2)	C17—C18—C19—C20	−0.6 (4)
C3—C2—C7—C6	1.4 (3)	C18—C19—C20—C21	0.6 (4)
C1—C2—C7—C6	−179.25 (19)	C19—C20—C21—C16	0.4 (3)
C2—C1—C8—O1	1.1 (2)	C17—C16—C21—C20	−1.3 (3)
S—C1—C8—O1	−178.27 (13)	S—C16—C21—C20	−177.88 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Clii	0.93	2.78	3.653 (3)	157
C20—H20···O2iii	0.93	2.47	3.261 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯Cli	0.93	2.78	3.653 (3)	157
C20—H20⋯O2ii	0.93	2.47	3.261 (3)	144

Symmetry codes: (i) ; (ii) .