N-[(4-Chloro­phen­yl)sulfon­yl]acetamide

Fun, H.-K.; Chia, T.S.; Jyothi, K.; Hegde, P.; D'Souza, P.R.

doi:10.1107/S1600536812033764

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2626

doi:10.1107/S1600536812033764

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N-[(4-Chlorophenyl)sulfonyl]acetamide

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a K. Jyothi,^b Poornima Hegde ^b and Pramila Rita D'Souza ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, St. Joseph Engineering College, Vamanjoor, Mangalore 575 028, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 July 2012; accepted 27 July 2012; online 4 August 2012)

The asymmetric unit of the title compound, C₈H₈ClNO₃S, consists of two crystallographically independent molecules (A and B). The dihedral angles between the benzene ring and amide C—C(=O)—NH– plane are 87.6 (3) (molecule A) and 86.0 (3)° (molecule B). In the crystal, the independent molecules are alternately linked by N—H⋯O hydrogen bonds into an infinite chain along the b axis. Short intermolecular Cl⋯Cl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed.

Related literature

For a related structure, see: Fun et al. (2012 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₈H₈ClNO₃S
M_r = 233.66
Monoclinic, P 2/c
a = 12.1801 (6) Å
b = 9.2529 (4) Å
c = 17.6769 (8) Å
β = 101.979 (1)°
V = 1948.83 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 100 K
0.36 × 0.14 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.819, T_max = 0.923
45479 measured reflections
7130 independent reflections
5439 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.090
S = 1.04
7130 reflections
263 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O3Aⁱ	0.871 (15)	1.939 (15)	2.7980 (10)	168.6 (13)
N1A—H1NA⋯O3Bⁱⁱ	0.865 (15)	1.939 (15)	2.7952 (10)	170.0 (13)
Symmetry codes: (i) x+1, y+1, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033764/is5173sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033764/is5173Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812033764/is5173Isup3.cml

checkCIF report

Comment top

In continuation to our reports on the biological activity of sulfonamide containing compounds (Fun et al., 2012), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules (A and B). The C═ O and N—H bonds in the amide planes [C7A/O3A/N1A/H1NA and C7B/O3B/N1B/H1NB; maximum deviations = 0.043 (5) Å at atom N1A and 0.047 (5) Å at atom H1NB] are trans to each other. The benzene ring (C1–C6) forms a dihedral angle of 87.6 (3)° with the amide plane in molecule A, whereas the corresponding angle is 86.0 (3)° in molecule B. The bond lengths and angles are comparable to those found in a related structure (Fun et al., 2012). In the crystal (Fig. 2), molecules are linked by intermolecular N1B—H1NB···O3A and N1A—H1NA···O3B hydrogen bonds (Table 1) into an infinite chain along the b axis. Short intermolecular Cl1A···Cl1A [3.2882 (5) Å; 1 - x, 1 - y, 1 - z] and Cl1B···Cl1B [3.2812 (5) Å; 1 - x, y, -1/2 - z] are also observed.

Related literature top

For a related structure, see: Fun et al. (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a vigorously stirred mixture of 4-chlorobenzenesulphonamide and silica sulfuric acid, acid chloride or acid anhydride was added at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added and the solid catalyst was removed by filtration. The filtrate was washed with water, dried and evaporated. The crude product was purified by recrystallization from an ethanol solution to yield colourless single crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed along the c axis. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

N-[(4-Chlorophenyl)sulfonyl]acetamide top

Crystal data top

C₈H₈ClNO₃S	F(000) = 960
M_r = 233.66	D_x = 1.593 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 9840 reflections
a = 12.1801 (6) Å	θ = 2.5–32.6°
b = 9.2529 (4) Å	µ = 0.59 mm⁻¹
c = 17.6769 (8) Å	T = 100 K
β = 101.979 (1)°	Block, colourless
V = 1948.83 (16) Å³	0.36 × 0.14 × 0.14 mm
Z = 8

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7130 independent reflections
Radiation source: fine-focus sealed tube	5439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
T_min = 0.819, T_max = 0.923	k = −14→13
45479 measured reflections	l = −26→26

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0436P)² + 0.5704P] where P = (F_o² + 2F_c²)/3
7130 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₈H₈ClNO₃S	V = 1948.83 (16) Å³
M_r = 233.66	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 12.1801 (6) Å	µ = 0.59 mm⁻¹
b = 9.2529 (4) Å	T = 100 K
c = 17.6769 (8) Å	0.36 × 0.14 × 0.14 mm
β = 101.979 (1)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7130 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5439 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.923	R_int = 0.033
45479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.48 e Å⁻³
7130 reflections	Δρ_min = −0.52 e Å⁻³
263 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl1A	0.47973 (2)	0.51064 (3)	0.405269 (18)	0.02673 (7)
S1A	0.170782 (19)	0.51977 (2)	0.076741 (14)	0.01367 (6)
O1A	0.19060 (6)	0.64897 (8)	0.03653 (4)	0.02048 (14)
O2A	0.17384 (6)	0.38233 (8)	0.04030 (4)	0.01910 (14)
O3A	0.03482 (6)	0.33069 (7)	0.15483 (4)	0.01845 (14)
N1A	0.04580 (7)	0.54746 (8)	0.09688 (5)	0.01463 (14)
C1A	0.29561 (8)	0.64713 (10)	0.20474 (6)	0.01909 (18)
H1AA	0.2712	0.7362	0.1802	0.023*
C2A	0.36445 (8)	0.64567 (11)	0.27788 (6)	0.02079 (19)
H2AA	0.3879	0.7335	0.3042	0.025*
C3A	0.39837 (8)	0.51313 (11)	0.31194 (6)	0.01803 (19)
C4A	0.36704 (8)	0.38278 (11)	0.27505 (6)	0.01842 (18)
H4AA	0.3926	0.2939	0.2994	0.022*
C5A	0.29771 (7)	0.38417 (10)	0.20193 (6)	0.01646 (17)
H5AA	0.2745	0.2962	0.1757	0.020*
C6A	0.26276 (8)	0.51635 (9)	0.16772 (6)	0.01437 (17)
C7A	−0.00697 (7)	0.44855 (9)	0.13606 (5)	0.01418 (16)
C8A	−0.11629 (9)	0.49932 (10)	0.15322 (7)	0.01856 (19)
H8AA	−0.1411	0.4314	0.1888	0.028*
H8AB	−0.1729	0.5044	0.1050	0.028*
H8AC	−0.1062	0.5953	0.1771	0.028*
Cl1B	0.52074 (2)	0.97797 (3)	−0.155284 (17)	0.02637 (7)
S1B	0.82941 (2)	1.00993 (2)	0.172976 (15)	0.01367 (6)
O1B	0.80290 (6)	1.13770 (8)	0.21146 (4)	0.01954 (14)
O2B	0.83407 (6)	0.87333 (8)	0.21118 (4)	0.01972 (14)
O3B	0.97057 (6)	0.83316 (7)	0.09436 (4)	0.01887 (14)
N1B	0.95264 (7)	1.04795 (8)	0.15212 (5)	0.01459 (14)
C1B	0.69388 (8)	1.12533 (10)	0.04604 (6)	0.01691 (17)
H1BA	0.7112	1.2157	0.0712	0.020*
C2B	0.62534 (8)	1.11904 (10)	−0.02700 (6)	0.01873 (18)
H2BA	0.5950	1.2048	−0.0526	0.022*
C3B	0.60174 (8)	0.98501 (11)	−0.06205 (6)	0.01785 (18)
C4B	0.64282 (8)	0.85698 (11)	−0.02594 (6)	0.01874 (18)
H4BA	0.6241	0.7667	−0.0508	0.022*
C5B	0.71197 (8)	0.86331 (10)	0.04738 (6)	0.01664 (17)
H5BA	0.7415	0.7773	0.0732	0.020*
C6B	0.73726 (8)	0.99763 (9)	0.08230 (6)	0.01408 (17)
C7B	1.00893 (7)	0.95272 (9)	0.11338 (5)	0.01431 (16)
C8B	1.11652 (8)	1.00994 (10)	0.09647 (7)	0.01848 (19)
H8BA	1.1475	0.9396	0.0651	0.028*
H8BB	1.1704	1.0264	0.1452	0.028*
H8BC	1.1019	1.1012	0.0681	0.028*
H1NB	0.9739 (11)	1.1378 (16)	0.1584 (8)	0.025 (3)*
H1NA	0.0217 (11)	0.6354 (16)	0.0901 (8)	0.026 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.02335 (13)	0.03545 (14)	0.01876 (15)	−0.00052 (9)	−0.00167 (10)	−0.00159 (9)
S1A	0.01605 (11)	0.01243 (10)	0.01325 (12)	0.00092 (7)	0.00468 (8)	0.00067 (7)
O1A	0.0248 (3)	0.0179 (3)	0.0203 (4)	−0.0010 (3)	0.0084 (3)	0.0060 (3)
O2A	0.0240 (3)	0.0163 (3)	0.0169 (3)	0.0032 (2)	0.0043 (3)	−0.0037 (2)
O3A	0.0202 (3)	0.0117 (3)	0.0232 (4)	−0.0001 (2)	0.0038 (3)	0.0033 (2)
N1A	0.0165 (3)	0.0101 (3)	0.0179 (4)	0.0015 (2)	0.0050 (3)	0.0020 (3)
C1A	0.0213 (4)	0.0135 (4)	0.0215 (5)	0.0011 (3)	0.0024 (4)	−0.0019 (3)
C2A	0.0220 (4)	0.0175 (4)	0.0219 (5)	0.0002 (3)	0.0022 (4)	−0.0048 (3)
C3A	0.0146 (4)	0.0225 (4)	0.0165 (5)	−0.0007 (3)	0.0024 (4)	−0.0009 (3)
C4A	0.0175 (4)	0.0177 (4)	0.0196 (5)	−0.0004 (3)	0.0027 (3)	0.0028 (3)
C5A	0.0166 (4)	0.0135 (4)	0.0190 (4)	−0.0004 (3)	0.0029 (3)	0.0010 (3)
C6A	0.0148 (4)	0.0132 (4)	0.0154 (5)	0.0002 (3)	0.0040 (3)	−0.0007 (3)
C7A	0.0156 (4)	0.0129 (4)	0.0137 (4)	−0.0015 (3)	0.0023 (3)	0.0001 (3)
C8A	0.0176 (4)	0.0199 (4)	0.0196 (5)	0.0018 (3)	0.0071 (4)	0.0023 (3)
Cl1B	0.02278 (12)	0.03587 (14)	0.01794 (14)	−0.00114 (9)	−0.00155 (10)	−0.00122 (9)
S1B	0.01612 (11)	0.01213 (9)	0.01342 (12)	−0.00106 (7)	0.00458 (9)	−0.00113 (7)
O1B	0.0222 (3)	0.0182 (3)	0.0193 (4)	0.0006 (2)	0.0067 (3)	−0.0061 (3)
O2B	0.0251 (3)	0.0159 (3)	0.0181 (3)	−0.0030 (2)	0.0044 (3)	0.0039 (2)
O3B	0.0216 (3)	0.0118 (3)	0.0227 (4)	0.0011 (2)	0.0033 (3)	−0.0030 (2)
N1B	0.0169 (3)	0.0099 (3)	0.0179 (4)	−0.0010 (2)	0.0055 (3)	−0.0013 (3)
C1B	0.0198 (4)	0.0125 (4)	0.0187 (4)	−0.0007 (3)	0.0047 (3)	0.0005 (3)
C2B	0.0192 (4)	0.0173 (4)	0.0193 (5)	0.0000 (3)	0.0032 (3)	0.0028 (3)
C3B	0.0143 (4)	0.0227 (4)	0.0162 (5)	−0.0008 (3)	0.0024 (4)	−0.0006 (3)
C4B	0.0174 (4)	0.0177 (4)	0.0203 (5)	−0.0007 (3)	0.0019 (3)	−0.0051 (3)
C5B	0.0167 (4)	0.0127 (4)	0.0200 (5)	0.0001 (3)	0.0027 (3)	−0.0022 (3)
C6B	0.0148 (4)	0.0125 (4)	0.0157 (5)	−0.0008 (3)	0.0048 (4)	−0.0010 (3)
C7B	0.0160 (4)	0.0126 (4)	0.0140 (4)	0.0022 (3)	0.0022 (3)	0.0004 (3)
C8B	0.0172 (4)	0.0192 (4)	0.0204 (5)	−0.0004 (3)	0.0071 (4)	−0.0006 (3)

Geometric parameters (Å, º) top

Cl1A—C3A	1.7394 (11)	Cl1B—C3B	1.7375 (11)
S1A—O2A	1.4295 (7)	S1B—O2B	1.4286 (7)
S1A—O1A	1.4366 (7)	S1B—O1B	1.4339 (7)
S1A—N1A	1.6537 (8)	S1B—N1B	1.6559 (8)
S1A—C6A	1.7591 (11)	S1B—C6B	1.7593 (11)
O3A—C7A	1.2200 (11)	O3B—C7B	1.2206 (11)
N1A—C7A	1.3839 (11)	N1B—C7B	1.3823 (11)
N1A—H1NA	0.865 (14)	N1B—H1NB	0.871 (14)
C1A—C2A	1.3873 (15)	C1B—C2B	1.3855 (14)
C1A—C6A	1.3943 (13)	C1B—C6B	1.3949 (13)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—C3A	1.3907 (14)	C2B—C3B	1.3895 (14)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.3864 (14)	C3B—C4B	1.3887 (14)
C4A—C5A	1.3897 (14)	C4B—C5B	1.3925 (14)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.3913 (13)	C5B—C6B	1.3934 (12)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.5012 (13)	C7B—C8B	1.4998 (13)
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800

O2A—S1A—O1A	119.64 (5)	O2B—S1B—O1B	119.73 (5)
O2A—S1A—N1A	110.25 (4)	O2B—S1B—N1B	110.14 (4)
O1A—S1A—N1A	103.55 (4)	O1B—S1B—N1B	103.54 (4)
O2A—S1A—C6A	108.95 (4)	O2B—S1B—C6B	109.19 (4)
O1A—S1A—C6A	109.08 (4)	O1B—S1B—C6B	108.77 (4)
N1A—S1A—C6A	104.24 (4)	N1B—S1B—C6B	104.31 (4)
C7A—N1A—S1A	123.31 (6)	C7B—N1B—S1B	122.73 (6)
C7A—N1A—H1NA	120.8 (9)	C7B—N1B—H1NB	120.4 (9)
S1A—N1A—H1NA	114.7 (9)	S1B—N1B—H1NB	115.7 (9)
C2A—C1A—C6A	119.21 (9)	C2B—C1B—C6B	119.35 (9)
C2A—C1A—H1AA	120.4	C2B—C1B—H1BA	120.3
C6A—C1A—H1AA	120.4	C6B—C1B—H1BA	120.3
C1A—C2A—C3A	118.68 (9)	C1B—C2B—C3B	118.81 (9)
C1A—C2A—H2AA	120.7	C1B—C2B—H2BA	120.6
C3A—C2A—H2AA	120.7	C3B—C2B—H2BA	120.6
C4A—C3A—C2A	122.38 (10)	C4B—C3B—C2B	122.34 (10)
C4A—C3A—Cl1A	118.79 (8)	C4B—C3B—Cl1B	118.92 (8)
C2A—C3A—Cl1A	118.81 (8)	C2B—C3B—Cl1B	118.73 (8)
C3A—C4A—C5A	118.96 (9)	C3B—C4B—C5B	118.85 (9)
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.6
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.6
C4A—C5A—C6A	118.98 (9)	C4B—C5B—C6B	119.03 (9)
C4A—C5A—H5AA	120.5	C4B—C5B—H5BA	120.5
C6A—C5A—H5AA	120.5	C6B—C5B—H5BA	120.5
C5A—C6A—C1A	121.79 (9)	C5B—C6B—C1B	121.61 (9)
C5A—C6A—S1A	119.51 (7)	C5B—C6B—S1B	120.13 (7)
C1A—C6A—S1A	118.67 (7)	C1B—C6B—S1B	118.23 (7)
O3A—C7A—N1A	121.09 (8)	O3B—C7B—N1B	120.88 (8)
O3A—C7A—C8A	124.21 (8)	O3B—C7B—C8B	124.43 (8)
N1A—C7A—C8A	114.69 (8)	N1B—C7B—C8B	114.68 (8)
C7A—C8A—H8AA	109.5	C7B—C8B—H8BA	109.5
C7A—C8A—H8AB	109.5	C7B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
C7A—C8A—H8AC	109.5	C7B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5

O2A—S1A—N1A—C7A	50.89 (9)	O2B—S1B—N1B—C7B	51.56 (9)
O1A—S1A—N1A—C7A	−179.98 (8)	O1B—S1B—N1B—C7B	−179.27 (8)
C6A—S1A—N1A—C7A	−65.90 (8)	C6B—S1B—N1B—C7B	−65.50 (8)
C6A—C1A—C2A—C3A	−0.07 (15)	C6B—C1B—C2B—C3B	0.04 (14)
C1A—C2A—C3A—C4A	0.83 (16)	C1B—C2B—C3B—C4B	1.14 (16)
C1A—C2A—C3A—Cl1A	−177.29 (8)	C1B—C2B—C3B—Cl1B	−177.27 (7)
C2A—C3A—C4A—C5A	−1.11 (16)	C2B—C3B—C4B—C5B	−1.32 (16)
Cl1A—C3A—C4A—C5A	177.02 (7)	Cl1B—C3B—C4B—C5B	177.08 (8)
C3A—C4A—C5A—C6A	0.60 (15)	C3B—C4B—C5B—C6B	0.32 (15)
C4A—C5A—C6A—C1A	0.14 (15)	C4B—C5B—C6B—C1B	0.83 (15)
C4A—C5A—C6A—S1A	−177.64 (7)	C4B—C5B—C6B—S1B	−177.14 (7)
C2A—C1A—C6A—C5A	−0.41 (15)	C2B—C1B—C6B—C5B	−1.02 (15)
C2A—C1A—C6A—S1A	177.39 (8)	C2B—C1B—C6B—S1B	176.99 (7)
O2A—S1A—C6A—C5A	−18.56 (9)	O2B—S1B—C6B—C5B	−21.27 (9)
O1A—S1A—C6A—C5A	−150.79 (8)	O1B—S1B—C6B—C5B	−153.56 (8)
N1A—S1A—C6A—C5A	99.12 (8)	N1B—S1B—C6B—C5B	96.44 (8)
O2A—S1A—C6A—C1A	163.58 (8)	O2B—S1B—C6B—C1B	160.70 (8)
O1A—S1A—C6A—C1A	31.36 (9)	O1B—S1B—C6B—C1B	28.41 (9)
N1A—S1A—C6A—C1A	−78.73 (8)	N1B—S1B—C6B—C1B	−81.59 (8)
S1A—N1A—C7A—O3A	−3.57 (13)	S1B—N1B—C7B—O3B	−1.87 (13)
S1A—N1A—C7A—C8A	175.90 (7)	S1B—N1B—C7B—C8B	177.08 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O3Aⁱ	0.871 (15)	1.939 (15)	2.7980 (10)	168.6 (13)
N1A—H1NA···O3Bⁱⁱ	0.865 (15)	1.939 (15)	2.7952 (10)	170.0 (13)

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

Experimental details

Crystal data
Chemical formula	C₈H₈ClNO₃S
M_r	233.66
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	100
a, b, c (Å)	12.1801 (6), 9.2529 (4), 17.6769 (8)
β (°)	101.979 (1)
V (Å³)	1948.83 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.36 × 0.14 × 0.14

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.819, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	45479, 7130, 5439
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.090, 1.04
No. of reflections	7130
No. of parameters	263
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.52

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O3Aⁱ	0.871 (15)	1.939 (15)	2.7980 (10)	168.6 (13)
N1A—H1NA···O3Bⁱⁱ	0.865 (15)	1.939 (15)	2.7952 (10)	170.0 (13)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors are grateful to the Visvesvaraya Technological University, Jnana Sangama, Belgaum, for financial support through research project grant No. VTU/Aca./2010–11/A-9/11330 Dtd. 07–12–2010.

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar