5-Chloro-7-methyl-2-phenyl-3-phenyl­sulfinyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536809024763

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1767

doi:10.1107/S1600536809024763

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5-Chloro-7-methyl-2-phenyl-3-phenylsulfinyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 26 June 2009; accepted 27 June 2009; online 4 July 2009)

In the title compound, C₂₁H₁₅ClO₂S, the O atom and the phenyl group of the phenylsulfinyl 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 intermolecular C—H⋯O and C—H⋯Cl interactions. In addition, the stacked molecules exhibit an intermolecular S⋯O interaction [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_r = 366.84
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.107
S = 1.06
3270 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) -x+1, -y+1, -z; (ii) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024763/ng2607sup1.cif

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

checkCIF report

Comment top

This work is related to our communications on the synthesis and structures of 5-chloro-1-benzofuran analogues, viz. 5-chloro-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007) and 5-chloro-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a). Here we report the crystal structure of the title compound (I), 5-chloro-7-methyl-2-phenyl-3-phenylsulfinyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle in (I) formed by the planes of the benzofuran and the 2-phenyl rings is 11.90 (9)°, and the phenyl ring (C16-C21) with 82.24 (7)° lies toward the benzofuran plane. The crystal packing (Fig. 2) is stabilized by intermolecular C–H···O and C–H···Cl interactions; the first between the phenyl H atom of the phenylsulfinyl substituent and the oxygen of the S═O unit, with a C20–H20···O2ⁱⁱ, the second between the phenyl H atom of the phenylsulfinyl substituent and the chlorine of the benzofuran ring, with a C19–H19···Clⁱ, respectively (Table 1 and Fig. 2). In addition, the crystal packing (Fig. 2) exhibits a sulfinyl-sulfinyl interaction (Choi et al., 2008b) interpreted as similar to a type-II carbonyl-carbonyl interaction (Allen et al., 1998), with S···O2ⁱⁱⁱ and O2···Sⁱⁱⁱ distance of 3.327 (2) Å.

Related literature top

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 top

The 77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 5-chloro-7-methyl-2-phenyl-3-phenylsulfanyl-1-benzofuran (351 mg, 1.0 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 462-463 K; R_f = 0.7 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. C–H···O, C–H···Cl, and S···O interactions (dotted lines) in the title compound. [Symmetry code: (i) -x + 1, -y + 1, -z; (ii) x + 1, y, z; (iii) -x, -y + 1, -z + 1; (iv) -1 +x, y, z.]

5-Chloro-7-methyl-2-phenyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₁₅ClO₂S	Z = 2
M_r = 366.84	F(000) = 380
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	3270 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −12→12
T_min = 0.910, T_max = 0.932	l = −13→13
6585 measured reflections

Refinement top

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(F_o²) + (0.0598P)² + 0.2839P] where P = (F_o² + 2F_c²)/3
3270 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₁H₁₅ClO₂S	γ = 81.483 (2)°
M_r = 366.84	V = 842.5 (2) Å³
Triclinic, P1	Z = 2
a = 8.224 (1) Å	Mo Kα radiation
b = 10.169 (1) Å	µ = 0.36 mm⁻¹
c = 11.083 (2) Å	T = 273 K
α = 68.771 (2)°	0.35 × 0.20 × 0.20 mm
β = 78.050 (2)°

Data collection top

Bruker SMART CCD diffractometer	3270 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2650 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.932	R_int = 0.018
6585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
3270 reflections	Δρ_min = −0.45 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (ii) −x+1, −y+1, −z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅ClO₂S
M_r	366.84
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.224 (1), 10.169 (1), 11.083 (2)
α, β, γ (°)	68.771 (2), 78.050 (2), 81.483 (2)
V (Å³)	842.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.910, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	6585, 3270, 2650
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.107, 1.06
No. of reflections	3270
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.45

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···Clⁱ	0.93	2.78	3.653 (3)	157.3
C20—H20···O2ⁱⁱ	0.93	2.47	3.261 (3)	143.5

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1291–o1292. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1061. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o1767

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