3-[(4-Chloro­phen­yl)sulfin­yl]-2,4,6,7-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536810042339

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3087

https://doi.org/10.1107/S1600536810042339

Open

access

3-[(4-Chlorophenyl)sulfinyl]-2,4,6,7-tetramethyl-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 6 October 2010; accepted 19 October 2010; online 6 November 2010)

In the title compound, C₁₈H₁₇ClO₂S, the 4-chlorophenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 87.49 (5)°]. In the crystal, molecules are linked through weak intermolecular C—H⋯π interactions, 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. (2010a ,b ,c ).

Experimental

Crystal data

C₁₈H₁₇ClO₂S
M_r = 332.83
Orthorhombic, P n a 2₁
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.090
S = 1.05
3392 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1382 Friedel pairs
Flack parameter: −0.03 (6)

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ ; (ii) x, y, z-1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810042339/bh2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042339/bh2316Isup2.hkl

checkCIF report

Comment top

A series of benzofuran ring system have received much attention in view of their interesting pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-chlorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report herein on the crystal structure of the title compound.

In the title molecule (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 4-chlorophenyl ring makes a dihedral angle of 87.49 (5)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···π interactions; the first one between a methyl H atom and the 4-chlorophenyl ring (C11—H11A···Cg1ⁱ; Table 1, Cg1 is the centroid of the C13···C18 4–chlorophenyl ring), and the second one between a methyl H atom and the benzene ring (C12—H12B···Cg2ⁱⁱ; Table 1, Cg2 is the centroid of the C2···C7 benzene ring). The title compound crystallizes in the non-centrosymmetric space group Pna2₁ in spite of having no asymmetric C atoms. The space group is caused by a right-hand pseudo-helix along the a axis (Fig. 2).

Related literature top

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. (2010a,b,c).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (348 mg, 1.0 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. 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. 442–443 K; R_f = 0.67 (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.

Structure description top

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. (2010a,b,c).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg1 and Cg2 denote the centroids of the C13···C18 4-chlorophenyl ring and the C2···C7 benzene ring, respectively. [Symmetry codes: (i) x-1/2, -y+3/2, z; (ii) x, y, z-1; (iii) x-1/2, -y+3/2, z; (iv) x, y, z+1].

3-[(4-Chlorophenyl)sulfinyl]-2,4,6,7-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇ClO₂S	D_x = 1.383 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0426P)² + 0.1096P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3392 reflections	Δρ_max = 0.20 e Å⁻³
203 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1382 Friedel pairs
0 constraints	Absolute structure parameter: −0.03 (6)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₈H₁₇ClO₂S	V = 1598.25 (9) Å³
M_r = 332.83	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.2329 (4) Å	µ = 0.37 mm⁻¹
b = 20.1499 (7) Å	T = 173 K
c = 6.4840 (2) Å	0.33 × 0.16 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3392 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2809 reflections with I > 2σ(I)
T_min = 0.651, T_max = 0.746	R_int = 0.034
8651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.20 e Å⁻³
S = 1.05	Δρ_min = −0.25 e Å⁻³
3392 reflections	Absolute structure: Flack (1983), 1382 Friedel pairs
203 parameters	Absolute structure parameter: −0.03 (6)
1 restraint

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇ClO₂S
M_r	332.83
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.2329 (4), 20.1499 (7), 6.4840 (2)
V (Å³)	1598.25 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.33 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.651, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8651, 3392, 2809
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.090, 1.05
No. of reflections	3392
No. of parameters	203
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25
Absolute structure	Flack (1983), 1382 Friedel pairs
Absolute structure parameter	−0.03 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

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)	148.2
C12—H12B···Cg2ⁱⁱ	0.96	2.83	3.653 (3)	143.9

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x, y, z−1.

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214–4226. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o2325. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2551. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o2702. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3087

https://doi.org/10.1107/S1600536810042339

Open

access