3-(3-Chloro­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812002887

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o534

doi:10.1107/S1600536812002887

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3-(3-Chlorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 12 January 2012; accepted 23 January 2012; online 31 January 2012)

In the title compound, C₁₈H₁₇ClO₂S, the 3-chlorophenyl ring makes a dihedral angle of 72.62 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits a slipped π–π interaction between the 3-chlorophenyl rings of adjacent molecules [centroid–centroid distance = 3.751 (2) Å, interplanar distance = 3.450 (2) Å and slippage = 1.472 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For the crystal structures of related compounds, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₈H₁₇ClO₂S
M_r = 332.83
Triclinic, $[P \overline 1]$
a = 7.4198 (1) Å
b = 7.9792 (1) Å
c = 14.5014 (2) Å
α = 105.965 (1)°
β = 95.732 (1)°
γ = 103.965 (1)°
V = 788.21 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 K
0.26 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.908, T_max = 0.911
14786 measured reflections
3897 independent reflections
3622 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 0.95
3897 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.98	2.60	3.5786 (16)	175
C12—H12A⋯O2ⁱⁱ	0.98	2.40	3.3159 (17)	155
C10—H10C⋯Cg1ⁱⁱⁱ	0.98	2.79	3.615 (16)	142
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y, -z.

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: 10.1107/S1600536812002887/ds2170sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002887/ds2170Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002887/ds2170Isup3.cml

checkCIF report

Comment top

Substituted benzofuran analogues have drawn much attention owing to their valuable biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing study of 2,4,6,7-tetramethyl-1-benzofuran derivatives containing either 3-(4-chlorophenylsulfinyl) (Choi et al., 2010) or 3-(3-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.018 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorophenyl ring and the mean plane of the benzofurn fragment is 72.62 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C– H···O and C–H···π interactions (Table 1, Cg1 is the centroid of the C2-C7 benzene ring). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between the 3-chlorophenyl rings of adjacent molecules, with a Cg2···Cg2^iv distance of 3.751 (2) Å and an interplanar distance of 3.450 (2) Å resulting in a slippage of 1.472 (2) Å (Cg2 is the centroid of the C13-C18 3-chlorophenyl ring).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (285 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 10h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 447-448 K; Rf = 0.52 (hexane-ethyl acetate, 4:1 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: 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···O, C–H···π, and π–π interactions (dottedlines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z; (ii) x + 1, y, z; (iii) -x + 1, -y, -z (iv) - -x + 1, - -y + 1, - z + 1; (v) -x - 1, -y, z.]

3-(3-Chlorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran top

Crystal data top

C₁₈H₁₇ClO₂S	Z = 2
M_r = 332.83	F(000) = 348
Triclinic, P1	D_x = 1.402 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4198 (1) Å	Cell parameters from 9057 reflections
b = 7.9792 (1) Å	θ = 2.7–28.3°
c = 14.5014 (2) Å	µ = 0.38 mm⁻¹
α = 105.965 (1)°	T = 173 K
β = 95.732 (1)°	Block, colourless
γ = 103.965 (1)°	0.26 × 0.25 × 0.25 mm
V = 788.21 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3897 independent reflections
Radiation source: rotating anode	3622 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.5°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.908, T_max = 0.911	l = −19→19
14786 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.099	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0638P)² + 0.3249P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₈H₁₇ClO₂S	γ = 103.965 (1)°
M_r = 332.83	V = 788.21 (2) Å³
Triclinic, P1	Z = 2
a = 7.4198 (1) Å	Mo Kα radiation
b = 7.9792 (1) Å	µ = 0.38 mm⁻¹
c = 14.5014 (2) Å	T = 173 K
α = 105.965 (1)°	0.26 × 0.25 × 0.25 mm
β = 95.732 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3897 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3622 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.911	R_int = 0.025
14786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.95	Δρ_max = 0.36 e Å⁻³
3897 reflections	Δρ_min = −0.39 e Å⁻³
203 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
S1	0.53130 (4)	0.65049 (4)	0.33172 (2)	0.02082 (9)
Cl1	−0.00317 (6)	0.23558 (6)	0.46616 (3)	0.04572 (13)
O1	0.79660 (12)	0.52179 (12)	0.11618 (6)	0.02335 (19)
O2	0.36498 (14)	0.72242 (13)	0.32004 (7)	0.0282 (2)
C1	0.59030 (17)	0.55512 (16)	0.21874 (8)	0.0202 (2)
C2	0.48969 (16)	0.40937 (15)	0.13006 (8)	0.0191 (2)
C3	0.30551 (17)	0.29506 (16)	0.09430 (9)	0.0212 (2)
C4	0.27547 (18)	0.17027 (17)	0.00165 (9)	0.0236 (2)
H4	0.1518	0.0915	−0.0247	0.028*
C5	0.41627 (19)	0.15371 (17)	−0.05513 (9)	0.0232 (2)
C6	0.59915 (18)	0.26984 (17)	−0.02096 (9)	0.0220 (2)
C7	0.62560 (17)	0.39462 (16)	0.07062 (8)	0.0204 (2)
C8	0.77070 (17)	0.61729 (17)	0.20508 (9)	0.0227 (2)
C9	0.14666 (18)	0.30115 (19)	0.15074 (9)	0.0270 (3)
H9A	0.0265	0.2612	0.1053	0.040*
H9B	0.1654	0.4257	0.1926	0.040*
H9C	0.1445	0.2205	0.1911	0.040*
C10	0.3716 (2)	0.00812 (19)	−0.15260 (9)	0.0297 (3)
H10A	0.4041	0.0640	−0.2033	0.045*
H10B	0.2366	−0.0561	−0.1674	0.045*
H10C	0.4450	−0.0781	−0.1504	0.045*
C11	0.7563 (2)	0.26059 (19)	−0.07831 (10)	0.0285 (3)
H11A	0.8681	0.3618	−0.0442	0.043*
H11B	0.7166	0.2685	−0.1431	0.043*
H11C	0.7866	0.1454	−0.0850	0.043*
C12	0.93714 (19)	0.7651 (2)	0.26499 (10)	0.0317 (3)
H12A	1.0409	0.7140	0.2781	0.048*
H12B	0.9046	0.8265	0.3268	0.048*
H12C	0.9761	0.8526	0.2298	0.048*
C13	0.44562 (18)	0.44638 (16)	0.36349 (8)	0.0211 (2)
C14	0.55149 (19)	0.32357 (18)	0.35979 (9)	0.0264 (3)
H14	0.6695	0.3438	0.3384	0.032*
C15	0.4822 (2)	0.17083 (18)	0.38788 (10)	0.0305 (3)
H15	0.5528	0.0854	0.3851	0.037*
C16	0.3106 (2)	0.14177 (18)	0.42004 (10)	0.0298 (3)
H16	0.2625	0.0365	0.4385	0.036*
C17	0.21090 (19)	0.26868 (19)	0.42478 (9)	0.0276 (3)
C18	0.27641 (18)	0.42257 (18)	0.39725 (9)	0.0246 (3)
H18	0.2069	0.5092	0.4015	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02414 (16)	0.01806 (15)	0.01927 (15)	0.00564 (11)	0.00480 (11)	0.00411 (11)
Cl1	0.0391 (2)	0.0496 (2)	0.0587 (3)	0.01101 (18)	0.02486 (18)	0.0286 (2)
O1	0.0202 (4)	0.0255 (4)	0.0230 (4)	0.0046 (3)	0.0058 (3)	0.0062 (3)
O2	0.0326 (5)	0.0247 (5)	0.0331 (5)	0.0151 (4)	0.0106 (4)	0.0104 (4)
C1	0.0211 (5)	0.0205 (5)	0.0193 (5)	0.0056 (4)	0.0043 (4)	0.0063 (4)
C2	0.0224 (6)	0.0177 (5)	0.0187 (5)	0.0062 (4)	0.0044 (4)	0.0074 (4)
C3	0.0224 (6)	0.0204 (5)	0.0217 (5)	0.0056 (4)	0.0054 (4)	0.0080 (4)
C4	0.0243 (6)	0.0204 (6)	0.0228 (6)	0.0022 (5)	0.0025 (4)	0.0055 (5)
C5	0.0306 (6)	0.0207 (6)	0.0190 (5)	0.0080 (5)	0.0049 (4)	0.0064 (4)
C6	0.0274 (6)	0.0222 (6)	0.0205 (5)	0.0093 (5)	0.0077 (4)	0.0096 (4)
C7	0.0207 (5)	0.0205 (5)	0.0214 (5)	0.0057 (4)	0.0040 (4)	0.0087 (4)
C8	0.0232 (6)	0.0231 (6)	0.0220 (5)	0.0069 (5)	0.0046 (4)	0.0068 (5)
C9	0.0215 (6)	0.0293 (6)	0.0255 (6)	0.0021 (5)	0.0064 (5)	0.0046 (5)
C10	0.0387 (7)	0.0249 (6)	0.0219 (6)	0.0073 (5)	0.0064 (5)	0.0027 (5)
C11	0.0311 (7)	0.0330 (7)	0.0247 (6)	0.0115 (5)	0.0118 (5)	0.0097 (5)
C12	0.0217 (6)	0.0333 (7)	0.0315 (7)	0.0010 (5)	0.0034 (5)	0.0027 (6)
C13	0.0265 (6)	0.0195 (5)	0.0163 (5)	0.0066 (4)	0.0034 (4)	0.0039 (4)
C14	0.0307 (6)	0.0254 (6)	0.0246 (6)	0.0113 (5)	0.0069 (5)	0.0066 (5)
C15	0.0421 (8)	0.0235 (6)	0.0288 (6)	0.0147 (6)	0.0068 (6)	0.0075 (5)
C16	0.0403 (7)	0.0216 (6)	0.0247 (6)	0.0040 (5)	0.0042 (5)	0.0075 (5)
C17	0.0294 (6)	0.0285 (6)	0.0228 (6)	0.0036 (5)	0.0064 (5)	0.0078 (5)
C18	0.0282 (6)	0.0258 (6)	0.0207 (6)	0.0088 (5)	0.0057 (5)	0.0070 (5)

Geometric parameters (Å, º) top

S1—O2	1.4949 (9)	C9—H9C	0.9800
S1—C1	1.7531 (12)	C10—H10A	0.9800
S1—C13	1.8001 (13)	C10—H10B	0.9800
Cl1—C17	1.7401 (14)	C10—H10C	0.9800
O1—C8	1.3635 (14)	C11—H11A	0.9800
O1—C7	1.3851 (14)	C11—H11B	0.9800
C1—C8	1.3651 (17)	C11—H11C	0.9800
C1—C2	1.4594 (16)	C12—H12A	0.9800
C2—C7	1.3960 (16)	C12—H12B	0.9800
C2—C3	1.4018 (17)	C12—H12C	0.9800
C3—C4	1.3941 (17)	C13—C18	1.3823 (17)
C3—C9	1.5032 (16)	C13—C14	1.3897 (17)
C4—C5	1.4020 (17)	C14—C15	1.3886 (19)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.3970 (18)	C15—C16	1.388 (2)
C5—C10	1.5081 (17)	C15—H15	0.9500
C6—C7	1.3856 (17)	C16—C17	1.382 (2)
C6—C11	1.5025 (17)	C16—H16	0.9500
C8—C12	1.4797 (18)	C17—C18	1.3870 (19)
C9—H9A	0.9800	C18—H18	0.9500
C9—H9B	0.9800

O2—S1—C1	111.44 (6)	C5—C10—H10B	109.5
O2—S1—C13	105.69 (6)	H10A—C10—H10B	109.5
C1—S1—C13	99.12 (5)	C5—C10—H10C	109.5
C8—O1—C7	106.80 (9)	H10A—C10—H10C	109.5
C8—C1—C2	107.14 (10)	H10B—C10—H10C	109.5
C8—C1—S1	118.34 (9)	C6—C11—H11A	109.5
C2—C1—S1	134.45 (9)	C6—C11—H11B	109.5
C7—C2—C3	118.68 (11)	H11A—C11—H11B	109.5
C7—C2—C1	104.27 (10)	C6—C11—H11C	109.5
C3—C2—C1	137.04 (11)	H11A—C11—H11C	109.5
C4—C3—C2	116.04 (11)	H11B—C11—H11C	109.5
C4—C3—C9	120.50 (11)	C8—C12—H12A	109.5
C2—C3—C9	123.45 (11)	C8—C12—H12B	109.5
C3—C4—C5	124.13 (12)	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	120.18 (11)	H12B—C12—H12C	109.5
C6—C5—C10	119.76 (11)	C18—C13—C14	121.49 (12)
C4—C5—C10	120.05 (12)	C18—C13—S1	117.34 (9)
C7—C6—C5	114.84 (11)	C14—C13—S1	121.06 (10)
C7—C6—C11	122.20 (12)	C15—C14—C13	118.97 (12)
C5—C6—C11	122.96 (11)	C15—C14—H14	120.5
O1—C7—C6	123.21 (11)	C13—C14—H14	120.5
O1—C7—C2	110.72 (10)	C16—C15—C14	120.63 (12)
C6—C7—C2	126.06 (11)	C16—C15—H15	119.7
O1—C8—C1	111.04 (11)	C14—C15—H15	119.7
O1—C8—C12	115.43 (11)	C17—C16—C15	118.86 (13)
C1—C8—C12	133.53 (12)	C17—C16—H16	120.6
C3—C9—H9A	109.5	C15—C16—H16	120.6
C3—C9—H9B	109.5	C16—C17—C18	121.86 (13)
H9A—C9—H9B	109.5	C16—C17—Cl1	119.46 (11)
C3—C9—H9C	109.5	C18—C17—Cl1	118.68 (11)
H9A—C9—H9C	109.5	C13—C18—C17	118.15 (12)
H9B—C9—H9C	109.5	C13—C18—H18	120.9
C5—C10—H10A	109.5	C17—C18—H18	120.9

O2—S1—C1—C8	125.23 (10)	C11—C6—C7—C2	−178.00 (11)
C13—S1—C1—C8	−123.83 (10)	C3—C2—C7—O1	177.83 (10)
O2—S1—C1—C2	−58.15 (13)	C1—C2—C7—O1	−1.15 (12)
C13—S1—C1—C2	52.78 (13)	C3—C2—C7—C6	−3.17 (18)
C8—C1—C2—C7	1.49 (13)	C1—C2—C7—C6	177.85 (11)
S1—C1—C2—C7	−175.39 (10)	C7—O1—C8—C1	0.63 (13)
C8—C1—C2—C3	−177.20 (13)	C7—O1—C8—C12	−178.36 (11)
S1—C1—C2—C3	5.9 (2)	C2—C1—C8—O1	−1.34 (14)
C7—C2—C3—C4	1.96 (16)	S1—C1—C8—O1	176.13 (8)
C1—C2—C3—C4	−179.49 (13)	C2—C1—C8—C12	177.39 (14)
C7—C2—C3—C9	−178.71 (11)	S1—C1—C8—C12	−5.1 (2)
C1—C2—C3—C9	−0.2 (2)	O2—S1—C13—C18	−17.61 (11)
C2—C3—C4—C5	0.39 (18)	C1—S1—C13—C18	−133.06 (10)
C9—C3—C4—C5	−178.96 (12)	O2—S1—C13—C14	166.23 (10)
C3—C4—C5—C6	−1.86 (19)	C1—S1—C13—C14	50.79 (11)
C3—C4—C5—C10	177.04 (12)	C18—C13—C14—C15	2.02 (19)
C4—C5—C6—C7	0.82 (17)	S1—C13—C14—C15	178.01 (10)
C10—C5—C6—C7	−178.09 (11)	C13—C14—C15—C16	−0.6 (2)
C4—C5—C6—C11	−179.50 (11)	C14—C15—C16—C17	−0.8 (2)
C10—C5—C6—C11	1.59 (18)	C15—C16—C17—C18	0.8 (2)
C8—O1—C7—C6	−178.65 (11)	C15—C16—C17—Cl1	−179.31 (10)
C8—O1—C7—C2	0.39 (13)	C14—C13—C18—C17	−2.01 (18)
C5—C6—C7—O1	−179.43 (10)	S1—C13—C18—C17	−178.15 (9)
C11—C6—C7—O1	0.88 (18)	C16—C17—C18—C13	0.59 (19)
C5—C6—C7—C2	1.68 (18)	Cl1—C17—C18—C13	−179.31 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.98	2.60	3.5786 (16)	175
C12—H12A···O2ⁱⁱ	0.98	2.40	3.3159 (17)	155
C10—H10C···Cg1ⁱⁱⁱ	0.98	2.79	3.615 (16)	142

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇ClO₂S
M_r	332.83
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.4198 (1), 7.9792 (1), 14.5014 (2)
α, β, γ (°)	105.965 (1), 95.732 (1), 103.965 (1)
V (Å³)	788.21 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.26 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.908, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	14786, 3897, 3622
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.099, 0.95
No. of reflections	3897
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.39

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 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.98	2.60	3.5786 (16)	175.0
C12—H12A···O2ⁱⁱ	0.98	2.40	3.3159 (17)	155.2
C10—H10C···Cg1ⁱⁱⁱ	0.98	2.79	3.615 (16)	142.4

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

Acknowledgements

This work was supported by Blue-Bio Industry Regional Innovation Center (grant No. RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

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Volume 68| Part 2| February 2012| Page o534

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