3-(4-Chloro­phenyl­sulfon­yl)-2-methyl­naphtho[1,2-b]furan

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

doi:10.1107/S1600536808009215

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o837

doi:10.1107/S1600536808009215

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3-(4-Chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan

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 28 March 2008; accepted 4 April 2008; online 16 April 2008)

The title compound, C₁₉H₁₃ClO₃S, was prepared by the oxidation of 3-(4-chlorophenylsulfanyl)-2-methylnaphtho[1,2-b]furan with 3-chloroperoxybenzoic acid. The 4-chlorophenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π interactions between a methyl H atom and the furan ring of an adjacent molecule. In addition, the crystal structure exhibits intermolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methylnaphtho[1,2-b]furan derivatives, see: Choi et al. (2006 , 2008 ).

Experimental

Crystal data

C₁₉H₁₃ClO₃S
M_r = 356.80
Orthorhombic, P n a 2₁
a = 8.1155 (3) Å
b = 18.6014 (7) Å
c = 10.8319 (4) Å
V = 1635.18 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 (2) K
0.60 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.842, T_max = 0.857
9543 measured reflections
2611 independent reflections
2532 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.066
S = 1.06
2611 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 728 Freidel pairs
Flack parameter: −0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the O1/C12/C1/C2/C11 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯Cg3ⁱ	0.98	2.89	3.488 (3)	120
C8—H8⋯O2ⁱⁱ	0.95	2.48	3.428 (2)	173
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808009215/at2553sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009215/at2553Isup2.hkl

checkCIF report

Comment top

This work is related to earlier communications on the synthesis and structure of 2-methylnaphtho[1,2-b]furan analogues, viz. 2-methyl-3-(methylsulfinyl) naphtho[1,2-b]furan (Choi et al., 2006) and 2-methyl-3-(phenylsulfonyl) naphtho[1,2-b]furan (Choi et al., 2008). Herein we report the molecular and crystal structure of the title compound, 3-(4-chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan (Fig. 1).

The naphthofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the thirteen constituent atoms. The 4-chlorophenyl ring (C13-C18) makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the benzene rings from the adjacent molecules. The Cg1···Cg2ⁱⁱⁱ distance is 3.635 (3) Å (Cg1 and Cg2 are the centroids of the C5-C10 benzene ring and the C2/C3/C4/C5/C10/C11 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between a methyl H atom and the furan ring of the naphthofuran unit, with a C19—H19A···Cg3ⁱ separation of 2.89 Å (Fig. 2 and Table 1; Cg3 is the centroid of the O1/C12/C1/C2/C11 furan ring; symmetry code as in Fig. 2). Additionally, intermolecular C—H···O interactions in the structure were observed (Fig. 2 and Table 1; symmetry code as in Fig. 2)

Related literature top

For the crystal structures of similar 2-methylnaphtho[1,2-b]furan derivatives, see: Choi et al. (2006, 2008).

Experimental top

3-Chloroperoxybenzoic acid (77%, 336 mg, 1.5 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2-methylnaphtho[1,2-b]furan (227 mg, 0.7 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 4 h, 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 colourless solid [yield 82 %, m.p. 427-428 K; R_f = 0.69 (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 acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.91 (s, 3H), 7.45-7.64 (m, 4H), 7.75 (d, J = 8.44 Hz, 1H), 7.90-8.02 (m, 4H), 8.21 (d, J = 8.04 Hz, 1H); EI-MS 358 [M+2], 356 [M⁺].

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, showing displacement ellipsoides drawn at the 50% probability level.
	Fig. 2. π—π, C—H···π and C—H···O interactions (dotted lines) in the structure of the title compound. Cg denotes the ring centroids. [Symmetry code: (i) x-1/2, -y+1/2, z; (ii) -x+3/2, y+1/2, z+1/2.]

3-(4-Chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan top

Crystal data top

C₁₉H₁₃ClO₃S	D_x = 1.449 Mg m⁻³
M_r = 356.80	Melting point = 427–428 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7325 reflections
a = 8.1155 (3) Å	θ = 2.2–28.2°
b = 18.6014 (7) Å	µ = 0.38 mm⁻¹
c = 10.8319 (4) Å	T = 173 K
V = 1635.18 (11) Å³	Block, colourless
Z = 4	0.60 × 0.40 × 0.40 mm
F(000) = 736

Data collection top

Bruker SMART CCD diffractometer	2611 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 2.7°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −23→23
T_min = 0.842, T_max = 0.857	l = −6→13
9543 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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0417P)² + 0.2762P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2611 reflections	Δρ_max = 0.26 e Å⁻³
218 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 728 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (5)

Crystal data top

C₁₉H₁₃ClO₃S	V = 1635.18 (11) Å³
M_r = 356.80	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.1155 (3) Å	µ = 0.38 mm⁻¹
b = 18.6014 (7) Å	T = 173 K
c = 10.8319 (4) Å	0.60 × 0.40 × 0.40 mm

Data collection top

Bruker SMART CCD diffractometer	2611 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2532 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.857	R_int = 0.016
9543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.066	Δρ_max = 0.26 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
2611 reflections	Absolute structure: Flack (1983), 728 Freidel pairs
218 parameters	Absolute structure parameter: −0.01 (5)
1 restraint

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	−0.09521 (6)	−0.07862 (3)	0.70659 (5)	0.04239 (14)
S	0.49747 (5)	0.08522 (2)	0.47158 (5)	0.02560 (10)
O1	0.55982 (14)	0.27683 (6)	0.61467 (14)	0.0294 (3)
O2	0.64177 (14)	0.04043 (6)	0.48194 (16)	0.0336 (3)
O3	0.44235 (16)	0.10742 (7)	0.35113 (14)	0.0344 (3)
C1	0.5352 (2)	0.16153 (8)	0.55974 (18)	0.0247 (3)
C2	0.62790 (19)	0.16344 (9)	0.67380 (18)	0.0256 (4)
C3	0.7034 (2)	0.11205 (9)	0.75222 (19)	0.0292 (4)
H3	0.6974	0.0621	0.7341	0.035*
C4	0.7847 (2)	0.13619 (9)	0.85426 (19)	0.0305 (4)
H4	0.8359	0.1022	0.9073	0.037*
C5	0.7955 (2)	0.21145 (10)	0.88442 (19)	0.0302 (4)
C6	0.8787 (2)	0.23535 (11)	0.9915 (2)	0.0386 (5)
H6	0.9282	0.2014	1.0456	0.046*
C7	0.8882 (3)	0.30743 (12)	1.0175 (2)	0.0449 (5)
H7	0.9442	0.3229	1.0898	0.054*
C8	0.8164 (3)	0.35875 (11)	0.9391 (2)	0.0421 (5)
H8	0.8249	0.4084	0.9585	0.051*
C9	0.7342 (2)	0.33765 (9)	0.8346 (2)	0.0347 (4)
H9	0.6858	0.3725	0.7817	0.042*
C10	0.7220 (2)	0.26328 (9)	0.80628 (19)	0.0280 (4)
C11	0.63904 (19)	0.23541 (8)	0.7025 (2)	0.0261 (3)
C12	0.4971 (2)	0.23071 (9)	0.5286 (2)	0.0280 (4)
C13	0.3328 (2)	0.03991 (8)	0.54446 (17)	0.0244 (3)
C14	0.3626 (2)	−0.01619 (9)	0.6257 (2)	0.0309 (4)
H14	0.4725	−0.0296	0.6455	0.037*
C15	0.2315 (2)	−0.05239 (10)	0.6775 (2)	0.0347 (4)
H15	0.2495	−0.0909	0.7335	0.042*
C16	0.0717 (2)	−0.03142 (10)	0.64619 (18)	0.0287 (4)
C17	0.0409 (2)	0.02495 (10)	0.5670 (2)	0.0297 (4)
H17	−0.0691	0.0385	0.5479	0.036*
C18	0.1726 (2)	0.06139 (9)	0.51591 (18)	0.0268 (4)
H18	0.1543	0.1008	0.4618	0.032*
C19	0.4122 (2)	0.26521 (10)	0.4225 (2)	0.0354 (4)
H19A	0.3484	0.3065	0.4519	0.053*
H19B	0.3379	0.2304	0.3835	0.053*
H19C	0.4941	0.2814	0.3622	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0366 (2)	0.0513 (3)	0.0393 (3)	−0.01236 (19)	0.0047 (2)	0.0104 (2)
S	0.02092 (18)	0.02869 (18)	0.0272 (2)	−0.00070 (14)	0.00189 (17)	−0.0036 (2)
O1	0.0279 (6)	0.0247 (5)	0.0357 (7)	−0.0001 (5)	0.0022 (6)	0.0033 (6)
O2	0.0221 (5)	0.0340 (6)	0.0447 (9)	0.0030 (5)	0.0019 (6)	−0.0096 (7)
O3	0.0317 (6)	0.0431 (7)	0.0285 (7)	−0.0038 (6)	0.0033 (6)	0.0006 (6)
C1	0.0212 (7)	0.0245 (7)	0.0284 (9)	−0.0012 (6)	0.0030 (7)	−0.0019 (7)
C2	0.0209 (7)	0.0273 (7)	0.0286 (10)	−0.0015 (6)	0.0043 (7)	−0.0023 (7)
C3	0.0298 (8)	0.0244 (8)	0.0335 (10)	0.0010 (6)	0.0024 (8)	0.0002 (7)
C4	0.0305 (8)	0.0300 (8)	0.0310 (10)	0.0027 (7)	0.0008 (8)	0.0011 (8)
C5	0.0246 (8)	0.0346 (9)	0.0314 (10)	−0.0023 (6)	0.0044 (8)	−0.0044 (8)
C6	0.0346 (9)	0.0471 (11)	0.0339 (12)	−0.0016 (8)	0.0003 (9)	−0.0045 (9)
C7	0.0432 (11)	0.0516 (11)	0.0401 (13)	−0.0097 (9)	−0.0022 (10)	−0.0154 (11)
C8	0.0436 (11)	0.0349 (9)	0.0478 (14)	−0.0115 (8)	0.0076 (10)	−0.0133 (9)
C9	0.0347 (9)	0.0287 (8)	0.0406 (11)	−0.0054 (7)	0.0085 (9)	−0.0035 (8)
C10	0.0243 (7)	0.0272 (8)	0.0326 (10)	−0.0025 (6)	0.0054 (8)	−0.0048 (7)
C11	0.0219 (7)	0.0250 (7)	0.0315 (9)	−0.0004 (6)	0.0052 (8)	0.0016 (8)
C12	0.0208 (7)	0.0301 (8)	0.0330 (10)	−0.0023 (6)	0.0029 (7)	0.0009 (8)
C13	0.0227 (7)	0.0257 (7)	0.0247 (9)	−0.0012 (6)	0.0003 (7)	−0.0036 (7)
C14	0.0272 (8)	0.0316 (8)	0.0338 (10)	0.0005 (7)	−0.0081 (8)	0.0026 (8)
C15	0.0373 (9)	0.0339 (9)	0.0330 (11)	−0.0025 (7)	−0.0074 (8)	0.0083 (8)
C16	0.0281 (8)	0.0336 (8)	0.0244 (10)	−0.0071 (7)	0.0010 (8)	−0.0012 (7)
C17	0.0235 (8)	0.0358 (9)	0.0299 (10)	0.0016 (6)	0.0007 (8)	−0.0011 (8)
C18	0.0268 (8)	0.0277 (7)	0.0261 (9)	0.0036 (6)	−0.0008 (7)	0.0001 (7)
C19	0.0321 (9)	0.0337 (9)	0.0403 (12)	0.0032 (7)	−0.0025 (9)	0.0059 (8)

Geometric parameters (Å, º) top

Cl—C16	1.7416 (17)	C7—H7	0.9500
S—O3	1.4397 (16)	C8—C9	1.371 (3)
S—O2	1.4416 (12)	C8—H8	0.9500
S—C1	1.7379 (17)	C9—C10	1.421 (2)
S—C13	1.7663 (17)	C9—H9	0.9500
O1—C12	1.365 (2)	C10—C11	1.409 (3)
O1—C11	1.383 (2)	C12—C19	1.485 (3)
C1—C12	1.366 (2)	C13—C14	1.386 (3)
C1—C2	1.447 (3)	C13—C18	1.394 (2)
C2—C11	1.377 (2)	C14—C15	1.379 (3)
C2—C3	1.418 (3)	C14—H14	0.9500
C3—C4	1.363 (3)	C15—C16	1.396 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.440 (2)	C16—C17	1.378 (3)
C4—H4	0.9500	C17—C18	1.382 (3)
C5—C6	1.414 (3)	C17—H17	0.9500
C5—C10	1.415 (3)	C18—H18	0.9500
C6—C7	1.372 (3)	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C7—C8	1.404 (3)	C19—H19C	0.9800

O3—S—O2	119.25 (10)	C11—C10—C5	115.35 (15)
O3—S—C1	108.57 (8)	C11—C10—C9	124.35 (18)
O2—S—C1	106.63 (8)	C5—C10—C9	120.30 (18)
O3—S—C13	107.87 (8)	C2—C11—O1	110.85 (17)
O2—S—C13	107.70 (8)	C2—C11—C10	124.68 (17)
C1—S—C13	106.11 (8)	O1—C11—C10	124.47 (14)
C12—O1—C11	107.04 (13)	O1—C12—C1	109.81 (17)
C12—C1—C2	107.78 (16)	O1—C12—C19	115.45 (14)
C12—C1—S	126.43 (15)	C1—C12—C19	134.68 (18)
C2—C1—S	125.51 (13)	C14—C13—C18	121.29 (16)
C11—C2—C3	119.46 (17)	C14—C13—S	120.70 (13)
C11—C2—C1	104.52 (15)	C18—C13—S	117.99 (13)
C3—C2—C1	136.01 (16)	C15—C14—C13	119.40 (16)
C4—C3—C2	118.21 (16)	C15—C14—H14	120.3
C4—C3—H3	120.9	C13—C14—H14	120.3
C2—C3—H3	120.9	C14—C15—C16	118.81 (17)
C3—C4—C5	122.26 (18)	C14—C15—H15	120.6
C3—C4—H4	118.9	C16—C15—H15	120.6
C5—C4—H4	118.9	C17—C16—C15	122.18 (16)
C6—C5—C10	118.56 (17)	C17—C16—Cl	118.45 (14)
C6—C5—C4	121.40 (19)	C15—C16—Cl	119.36 (15)
C10—C5—C4	120.04 (18)	C16—C17—C18	118.83 (16)
C7—C6—C5	120.1 (2)	C16—C17—H17	120.6
C7—C6—H6	119.9	C18—C17—H17	120.6
C5—C6—H6	119.9	C17—C18—C13	119.47 (16)
C6—C7—C8	121.1 (2)	C17—C18—H18	120.3
C6—C7—H7	119.4	C13—C18—H18	120.3
C8—C7—H7	119.4	C12—C19—H19A	109.5
C9—C8—C7	120.42 (18)	C12—C19—H19B	109.5
C9—C8—H8	119.8	H19A—C19—H19B	109.5
C7—C8—H8	119.8	C12—C19—H19C	109.5
C8—C9—C10	119.4 (2)	H19A—C19—H19C	109.5
C8—C9—H9	120.3	H19B—C19—H19C	109.5
C10—C9—H9	120.3

O3—S—C1—C12	8.85 (18)	C1—C2—C11—C10	−178.97 (16)
O2—S—C1—C12	138.51 (16)	C12—O1—C11—C2	−0.01 (19)
C13—S—C1—C12	−106.87 (16)	C12—O1—C11—C10	179.12 (15)
O3—S—C1—C2	−164.41 (14)	C5—C10—C11—C2	−0.7 (2)
O2—S—C1—C2	−34.74 (17)	C9—C10—C11—C2	179.39 (17)
C13—S—C1—C2	79.88 (16)	C5—C10—C11—O1	−179.69 (16)
C12—C1—C2—C11	−0.25 (19)	C9—C10—C11—O1	0.4 (3)
S—C1—C2—C11	174.06 (13)	C11—O1—C12—C1	−0.16 (19)
C12—C1—C2—C3	−179.16 (19)	C11—O1—C12—C19	−177.64 (15)
S—C1—C2—C3	−4.9 (3)	C2—C1—C12—O1	0.26 (19)
C11—C2—C3—C4	0.1 (2)	S—C1—C12—O1	−173.98 (12)
C1—C2—C3—C4	178.91 (18)	C2—C1—C12—C19	177.06 (19)
C2—C3—C4—C5	0.2 (3)	S—C1—C12—C19	2.8 (3)
C3—C4—C5—C6	179.21 (18)	O3—S—C13—C14	147.32 (16)
C3—C4—C5—C10	−0.7 (3)	O2—S—C13—C14	17.39 (18)
C10—C5—C6—C7	−0.5 (3)	C1—S—C13—C14	−96.49 (16)
C4—C5—C6—C7	179.54 (19)	O3—S—C13—C18	−31.49 (16)
C5—C6—C7—C8	−0.1 (3)	O2—S—C13—C18	−161.42 (14)
C6—C7—C8—C9	0.4 (3)	C1—S—C13—C18	84.70 (16)
C7—C8—C9—C10	0.0 (3)	C18—C13—C14—C15	1.3 (3)
C6—C5—C10—C11	−179.00 (16)	S—C13—C14—C15	−177.48 (16)
C4—C5—C10—C11	0.9 (2)	C13—C14—C15—C16	0.1 (3)
C6—C5—C10—C9	0.9 (3)	C14—C15—C16—C17	−1.1 (3)
C4—C5—C10—C9	−179.14 (17)	C14—C15—C16—Cl	177.77 (16)
C8—C9—C10—C11	179.23 (17)	C15—C16—C17—C18	0.7 (3)
C8—C9—C10—C5	−0.7 (3)	Cl—C16—C17—C18	−178.19 (15)
C3—C2—C11—O1	179.29 (14)	C16—C17—C18—C13	0.7 (3)
C1—C2—C11—O1	0.16 (19)	C14—C13—C18—C17	−1.7 (3)
C3—C2—C11—C10	0.2 (3)	S—C13—C18—C17	177.10 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg3ⁱ	0.98	2.89	3.488 (3)	120
C8—H8···O2ⁱⁱ	0.95	2.48	3.428 (2)	173

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃ClO₃S
M_r	356.80
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	8.1155 (3), 18.6014 (7), 10.8319 (4)
V (Å³)	1635.18 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.60 × 0.40 × 0.40

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.842, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections	9543, 2611, 2532
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.066, 1.06
No. of reflections	2611
No. of parameters	218
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20
Absolute structure	Flack (1983), 728 Freidel pairs
Absolute structure parameter	−0.01 (5)

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—H19A···Cg3ⁱ	0.98	2.89	3.488 (3)	120.4
C8—H8···O2ⁱⁱ	0.95	2.48	3.428 (2)	172.8

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

References

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. (2008). Acta Cryst. E64, o452. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Woo, H. M., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o3883–o3884. 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
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 64| Part 5| May 2008| Page o837

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