4-Chloro-N-(3,5-dimethyl­phen­yl)benzene­sulfonamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811028819

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2102

doi:10.1107/S1600536811028819

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4-Chloro-N-(3,5-dimethylphenyl)benzenesulfonamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 22 June 2011; accepted 17 July 2011; online 23 July 2011)

The asymmetric unit of the title compound, C₁₄H₁₄ClNO₂S, contains two independent molecules, which are twisted at the S atoms with C—SO₂—NH—C torsion angles of −69.4 (7)° and 66.0 (8)°. The sulfonyl and the anilino benzene rings are tilted relative to each other by 49.0 (4) and 61.7 (3)° in the two molecules. In the crystal, the molecules are linked into chains by N—H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For our studies of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2006 ), on N-(aryl)arylsulfonamides, see: Nirmala et al. (2009 ); Shakuntala et al. (2011a ,b ) and on N-(aryl)methanesulfonamides, see: Gowda et al. (2007 ).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 295.77
Orthorhombic, P b c a
a = 21.990 (2) Å
b = 10.0470 (8) Å
c = 26.408 (2) Å
V = 5834.4 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.856, T_max = 0.976
21403 measured reflections
5320 independent reflections
2694 reflections with I > 2σ(I)
R_int = 0.106

Refinement

R[F² > 2σ(F²)] = 0.128
wR(F²) = 0.345
S = 1.07
5320 reflections
347 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.49	3.001 (9)	119
N2—H2A⋯O1ⁱⁱ	0.86	2.39	3.006 (9)	130
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028819/ds2123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028819/ds2123Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028819/ds2123Isup3.cml

checkCIF report

Comment top

The sulfonamide moieties are the constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As a part of our work on the substituent effects on the structures and other aspects of this class of compounds (Gowda et al., 2006, 2007; Nirmala et al., 2009; Shakuntala et al., 2011a,b), in the present work, the crystal structure of 4-chloro-N-(3,5-dimethylphenyl)- benzenesulfonamide (I) has been determined (Fig.1). The asymmetric unit of the structure contains two independent molecules. The molecules are twisted at the S atoms with the C—SO₂—NH—C torsion angles of -69.5 (7)° and 66.1 (8)° in the two molecules, compared to the values of 65.3 (2)° and 54.6 (2)° in the two independent molecules of 4-chloro-N-(2,5-dimethylphenyl)-benzenesulfonamide (II) (Shakuntala et al., 2011b), and -53.8 (3)° and -63.4 (3)° in the two molecules of 4-chloro-N-(phenyl)-benzenesulfonamide (III) (Shakuntala et al., 2011a) and 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide (IV)(Nirmala et al., 2009).

The sulfonyl and the anilino benzene rings in the two independent molecules of (I) are tilted relative to each other by 49.0 (4)° (molecule 1) and 61.7 (3)° (molecule 2), compared to the values of 59.3 (1)° (molecule 1) and 45.8 (1)° (molecule 2) in (II), -53.8 (3)° and -63.4 (3)° in the two independent molecules of (III), and 54.6 (1)° in (IV)

In the title compound the molecules are linked into chains by N—H···O(S) hydrogen bonding (Table 1 and Fig.2).

Related literature top

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our studies of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2006), on N-(aryl)arylsulfonamides, see: Nirmala et al. (2009); Shakuntala et al. (2011a,b) and on N-(aryl)methanesulfonamides, see: Gowda et al. (2007).

Experimental top

The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 3,5-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(3,5-dimethylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from aqueous ethanol. The compound was characterized by recording its infrared and NMR spectra.

Prism like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Chloro-N-(3,5-dimethylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₄ClNO₂S	F(000) = 2464
M_r = 295.77	D_x = 1.347 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2329 reflections
a = 21.990 (2) Å	θ = 2.5–27.8°
b = 10.0470 (8) Å	µ = 0.40 mm⁻¹
c = 26.408 (2) Å	T = 293 K
V = 5834.4 (8) Å³	Prism, colourless
Z = 16	0.40 × 0.20 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5320 independent reflections
Radiation source: fine-focus sealed tube	2694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
Rotation method data acquisition using ω scans.	θ_max = 25.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→26
T_min = 0.856, T_max = 0.976	k = −9→12
21403 measured reflections	l = −25→31

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)] = 0.128	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.345	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1148P)² + 41.4199P] where P = (F_o² + 2F_c²)/3
5320 reflections	(Δ/σ)_max = 0.003
347 parameters	Δρ_max = 1.06 e Å⁻³
1 restraint	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₄ClNO₂S	V = 5834.4 (8) Å³
M_r = 295.77	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 21.990 (2) Å	µ = 0.40 mm⁻¹
b = 10.0470 (8) Å	T = 293 K
c = 26.408 (2) Å	0.40 × 0.20 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	5320 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2694 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.976	R_int = 0.106
21403 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.128	1 restraint
wR(F²) = 0.345	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1148P)² + 41.4199P] where P = (F_o² + 2F_c²)/3
5320 reflections	Δρ_max = 1.06 e Å⁻³
347 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

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
Cl1	0.00034 (14)	0.0421 (4)	0.59314 (17)	0.1103 (14)
S1	0.26317 (10)	0.0246 (2)	0.50757 (9)	0.0454 (6)
O1	0.3036 (3)	0.0914 (6)	0.5418 (2)	0.0544 (17)
O2	0.2769 (3)	−0.1061 (6)	0.4911 (3)	0.0547 (17)
N1	0.2594 (3)	0.1192 (7)	0.4583 (3)	0.0456 (18)
H1A	0.2778	0.1947	0.4587	0.055*
C1	0.1902 (4)	0.0237 (9)	0.5340 (3)	0.047 (2)
C2	0.1472 (5)	−0.0646 (11)	0.5157 (5)	0.070 (3)
H2	0.1570	−0.1267	0.4910	0.084*
C3	0.0889 (5)	−0.0574 (12)	0.5355 (5)	0.082 (4)
H3	0.0593	−0.1163	0.5242	0.098*
C4	0.0746 (5)	0.0348 (11)	0.5713 (5)	0.065 (3)
C5	0.1174 (5)	0.1204 (11)	0.5888 (4)	0.069 (3)
H5	0.1075	0.1818	0.6138	0.083*
C6	0.1749 (4)	0.1166 (10)	0.5699 (4)	0.056 (3)
H6	0.2039	0.1770	0.5814	0.068*
C7	0.2264 (3)	0.0807 (8)	0.4140 (3)	0.037 (2)
C8	0.1732 (4)	0.1481 (9)	0.4019 (3)	0.044 (2)
H8	0.1583	0.2126	0.4239	0.053*
C9	0.1421 (4)	0.1212 (10)	0.3577 (4)	0.049 (2)
C10	0.1645 (4)	0.0205 (10)	0.3270 (4)	0.054 (2)
H10	0.1435	−0.0003	0.2974	0.065*
C11	0.2166 (5)	−0.0504 (10)	0.3383 (4)	0.057 (3)
C12	0.2471 (4)	−0.0189 (9)	0.3823 (3)	0.049 (2)
H12	0.2822	−0.0655	0.3907	0.058*
C13	0.0873 (4)	0.2025 (12)	0.3421 (4)	0.074 (3)
H13A	0.0989	0.2941	0.3383	0.088*
H13B	0.0563	0.1954	0.3676	0.088*
H13C	0.0717	0.1697	0.3105	0.088*
C14	0.2416 (5)	−0.1558 (11)	0.3035 (4)	0.070 (3)
H14A	0.2404	−0.1242	0.2693	0.084*
H14B	0.2174	−0.2350	0.3064	0.084*
H14C	0.2828	−0.1754	0.3128	0.084*
Cl2	0.09120 (19)	0.4163 (3)	0.22721 (16)	0.1050 (13)
S2	0.13516 (12)	1.0127 (3)	0.17349 (10)	0.0600 (8)
O3	0.1989 (3)	1.0367 (8)	0.1698 (3)	0.085 (2)
O4	0.0976 (4)	1.0924 (8)	0.2066 (3)	0.081 (2)
N2	0.1092 (3)	1.0317 (8)	0.1159 (3)	0.0504 (19)
H2A	0.1342	1.0514	0.0920	0.061*
C15	0.1242 (4)	0.8416 (10)	0.1887 (3)	0.048 (2)
C16	0.1665 (5)	0.7509 (12)	0.1776 (4)	0.065 (3)
H16	0.2030	0.7759	0.1625	0.078*
C17	0.1549 (5)	0.6177 (11)	0.1893 (4)	0.069 (3)
H17	0.1832	0.5524	0.1809	0.083*
C18	0.1036 (5)	0.5848 (11)	0.2123 (4)	0.062 (3)
C19	0.0606 (5)	0.6750 (12)	0.2248 (4)	0.071 (3)
H19	0.0243	0.6488	0.2398	0.085*
C20	0.0720 (4)	0.8036 (11)	0.2150 (4)	0.058 (3)
H20	0.0447	0.8683	0.2258	0.070*
C21	0.0456 (4)	1.0162 (9)	0.1041 (3)	0.042 (2)
C22	0.0300 (4)	0.9218 (9)	0.0686 (3)	0.044 (2)
H22	0.0596	0.8654	0.0556	0.053*
C23	−0.0305 (4)	0.9104 (9)	0.0518 (3)	0.046 (2)
C24	−0.0726 (4)	0.9957 (9)	0.0725 (4)	0.052 (2)
H24	−0.1127	0.9909	0.0615	0.063*
C25	−0.0572 (4)	1.0907 (9)	0.1101 (4)	0.050 (2)
C26	0.0030 (4)	1.0975 (9)	0.1251 (3)	0.044 (2)
H26	0.0144	1.1584	0.1498	0.053*
C27	−0.0480 (4)	0.8106 (10)	0.0130 (4)	0.057 (3)
H27A	−0.0597	0.7292	0.0293	0.068*
H27B	−0.0141	0.7940	−0.0090	0.068*
H27C	−0.0815	0.8440	−0.0066	0.068*
C28	−0.1049 (5)	1.1804 (13)	0.1316 (5)	0.086 (4)
H28A	−0.1370	1.1277	0.1459	0.104*
H28B	−0.1210	1.2359	0.1052	0.104*
H28C	−0.0872	1.2352	0.1575	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0679 (19)	0.107 (3)	0.156 (4)	−0.008 (2)	0.046 (2)	0.006 (3)
S1	0.0432 (12)	0.0429 (13)	0.0501 (13)	0.0036 (10)	−0.0105 (10)	−0.0032 (11)
O1	0.046 (4)	0.060 (4)	0.057 (4)	0.001 (3)	−0.022 (3)	−0.009 (3)
O2	0.065 (4)	0.039 (4)	0.061 (4)	0.008 (3)	−0.010 (3)	−0.001 (3)
N1	0.047 (4)	0.053 (5)	0.037 (4)	−0.011 (3)	−0.007 (3)	−0.006 (4)
C1	0.049 (5)	0.041 (5)	0.051 (5)	−0.003 (4)	−0.013 (4)	0.000 (5)
C2	0.053 (6)	0.066 (7)	0.091 (8)	−0.006 (5)	−0.001 (6)	−0.022 (6)
C3	0.058 (7)	0.069 (8)	0.119 (11)	−0.021 (6)	−0.001 (7)	−0.015 (8)
C4	0.059 (6)	0.046 (6)	0.091 (8)	0.005 (5)	0.013 (6)	0.011 (6)
C5	0.076 (8)	0.064 (7)	0.067 (7)	−0.007 (6)	0.013 (6)	−0.013 (6)
C6	0.054 (6)	0.067 (7)	0.048 (6)	−0.004 (5)	0.002 (5)	−0.005 (5)
C7	0.031 (4)	0.036 (5)	0.044 (5)	−0.004 (4)	−0.008 (4)	0.005 (4)
C8	0.043 (5)	0.046 (5)	0.043 (5)	0.001 (4)	−0.004 (4)	−0.005 (4)
C9	0.038 (5)	0.063 (6)	0.046 (5)	0.002 (4)	0.000 (4)	0.006 (5)
C10	0.053 (6)	0.065 (7)	0.044 (5)	−0.002 (5)	−0.014 (4)	0.004 (5)
C11	0.066 (6)	0.061 (6)	0.045 (6)	−0.003 (5)	0.000 (5)	−0.006 (5)
C12	0.049 (5)	0.053 (6)	0.044 (5)	0.008 (5)	−0.006 (4)	0.004 (5)
C13	0.049 (6)	0.094 (9)	0.079 (8)	0.009 (6)	−0.012 (5)	0.016 (7)
C14	0.080 (7)	0.075 (8)	0.054 (6)	0.009 (6)	−0.010 (6)	−0.021 (6)
Cl2	0.124 (3)	0.075 (2)	0.116 (3)	−0.007 (2)	−0.004 (2)	0.035 (2)
S2	0.0554 (15)	0.0633 (17)	0.0614 (16)	−0.0026 (13)	−0.0178 (13)	−0.0092 (14)
O3	0.048 (4)	0.096 (6)	0.111 (6)	−0.020 (4)	−0.028 (4)	0.009 (5)
O4	0.103 (6)	0.087 (6)	0.052 (4)	0.022 (5)	−0.020 (4)	−0.028 (4)
N2	0.038 (4)	0.068 (5)	0.046 (4)	−0.007 (4)	−0.002 (3)	0.007 (4)
C15	0.049 (5)	0.053 (6)	0.041 (5)	0.004 (5)	−0.019 (4)	0.002 (5)
C16	0.061 (6)	0.072 (8)	0.063 (7)	−0.004 (6)	−0.001 (5)	−0.012 (6)
C17	0.075 (8)	0.063 (7)	0.070 (8)	0.021 (6)	0.010 (6)	−0.004 (6)
C18	0.069 (7)	0.069 (7)	0.049 (6)	0.004 (6)	0.001 (5)	0.008 (5)
C19	0.058 (6)	0.079 (6)	0.074 (8)	−0.003 (6)	0.003 (6)	0.017 (7)
C20	0.051 (6)	0.066 (5)	0.059 (6)	0.005 (5)	0.010 (5)	−0.012 (5)
C21	0.041 (5)	0.042 (5)	0.044 (5)	−0.002 (4)	0.004 (4)	0.007 (4)
C22	0.044 (5)	0.046 (5)	0.043 (5)	0.005 (4)	0.005 (4)	0.004 (4)
C23	0.037 (5)	0.052 (6)	0.048 (5)	0.000 (4)	0.001 (4)	0.002 (5)
C24	0.042 (5)	0.057 (6)	0.057 (6)	0.000 (4)	−0.002 (4)	0.004 (5)
C25	0.042 (5)	0.058 (6)	0.050 (6)	0.010 (4)	0.009 (4)	−0.005 (5)
C26	0.045 (5)	0.046 (6)	0.042 (5)	0.000 (4)	0.003 (4)	−0.009 (4)
C27	0.054 (6)	0.058 (6)	0.058 (6)	0.002 (5)	−0.008 (5)	−0.005 (5)
C28	0.065 (7)	0.093 (9)	0.102 (10)	0.019 (7)	−0.003 (7)	−0.021 (8)

Geometric parameters (Å, º) top

Cl1—C4	1.732 (10)	Cl2—C18	1.760 (11)
S1—O2	1.416 (6)	S2—O3	1.425 (7)
S1—O1	1.434 (6)	S2—O4	1.445 (8)
S1—N1	1.613 (7)	S2—N2	1.636 (7)
S1—C1	1.750 (9)	S2—C15	1.782 (10)
N1—C7	1.429 (10)	N2—C21	1.442 (10)
N1—H1A	0.8600	N2—H2A	0.8600
C1—C6	1.374 (13)	C15—C16	1.335 (13)
C1—C2	1.383 (13)	C15—C20	1.394 (13)
C2—C3	1.384 (14)	C16—C17	1.396 (15)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.361 (16)	C17—C18	1.323 (15)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.357 (15)	C18—C19	1.351 (15)
C5—C6	1.360 (13)	C19—C20	1.342 (14)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.382 (12)	C21—C26	1.361 (11)
C7—C8	1.390 (11)	C21—C22	1.378 (12)
C8—C9	1.380 (12)	C22—C23	1.406 (12)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.387 (13)	C23—C24	1.376 (12)
C9—C13	1.513 (12)	C23—C27	1.485 (12)
C10—C11	1.382 (13)	C24—C25	1.417 (13)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.377 (12)	C25—C26	1.383 (12)
C11—C14	1.505 (13)	C25—C28	1.495 (13)
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600

O2—S1—O1	119.7 (4)	O3—S2—O4	120.6 (5)
O2—S1—N1	108.0 (4)	O3—S2—N2	105.0 (5)
O1—S1—N1	105.4 (4)	O4—S2—N2	107.4 (4)
O2—S1—C1	108.2 (4)	O3—S2—C15	108.2 (5)
O1—S1—C1	108.6 (4)	O4—S2—C15	108.7 (5)
N1—S1—C1	106.1 (4)	N2—S2—C15	106.0 (4)
C7—N1—S1	121.8 (6)	C21—N2—S2	121.8 (6)
C7—N1—H1A	119.1	C21—N2—H2A	119.1
S1—N1—H1A	119.1	S2—N2—H2A	119.1
C6—C1—C2	120.6 (9)	C16—C15—C20	119.8 (10)
C6—C1—S1	119.7 (7)	C16—C15—S2	120.9 (8)
C2—C1—S1	119.5 (8)	C20—C15—S2	119.2 (8)
C3—C2—C1	117.9 (10)	C15—C16—C17	118.6 (10)
C3—C2—H2	121.1	C15—C16—H16	120.7
C1—C2—H2	121.1	C17—C16—H16	120.7
C4—C3—C2	120.8 (10)	C18—C17—C16	119.7 (10)
C4—C3—H3	119.6	C18—C17—H17	120.1
C2—C3—H3	119.6	C16—C17—H17	120.1
C5—C4—C3	120.4 (10)	C17—C18—C19	122.8 (11)
C5—C4—Cl1	121.0 (9)	C17—C18—Cl2	118.4 (9)
C3—C4—Cl1	118.6 (9)	C19—C18—Cl2	118.7 (9)
C4—C5—C6	120.3 (11)	C20—C19—C18	117.8 (11)
C4—C5—H5	119.9	C20—C19—H19	121.1
C6—C5—H5	119.9	C18—C19—H19	121.1
C5—C6—C1	119.9 (10)	C19—C20—C15	120.9 (10)
C5—C6—H6	120.0	C19—C20—H20	119.5
C1—C6—H6	120.0	C15—C20—H20	119.5
C12—C7—C8	119.3 (8)	C26—C21—C22	121.3 (8)
C12—C7—N1	121.7 (7)	C26—C21—N2	121.0 (8)
C8—C7—N1	119.0 (8)	C22—C21—N2	117.6 (8)
C9—C8—C7	121.2 (8)	C21—C22—C23	120.4 (8)
C9—C8—H8	119.4	C21—C22—H22	119.8
C7—C8—H8	119.4	C23—C22—H22	119.8
C8—C9—C10	117.4 (8)	C24—C23—C22	117.3 (9)
C8—C9—C13	121.3 (9)	C24—C23—C27	121.5 (8)
C10—C9—C13	121.2 (9)	C22—C23—C27	121.2 (8)
C11—C10—C9	122.9 (9)	C23—C24—C25	122.6 (8)
C11—C10—H10	118.5	C23—C24—H24	118.7
C9—C10—H10	118.5	C25—C24—H24	118.7
C12—C11—C10	117.9 (9)	C26—C25—C24	117.5 (8)
C12—C11—C14	119.9 (9)	C26—C25—C28	122.2 (9)
C10—C11—C14	122.2 (9)	C24—C25—C28	120.3 (9)
C11—C12—C7	121.2 (9)	C21—C26—C25	120.8 (8)
C11—C12—H12	119.4	C21—C26—H26	119.6
C7—C12—H12	119.4	C25—C26—H26	119.6
C9—C13—H13A	109.5	C23—C27—H27A	109.5
C9—C13—H13B	109.5	C23—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C9—C13—H13C	109.5	C23—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C11—C14—H14A	109.5	C25—C28—H28A	109.5
C11—C14—H14B	109.5	C25—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C11—C14—H14C	109.5	C25—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

O2—S1—N1—C7	46.5 (7)	O3—S2—N2—C21	−179.5 (7)
O1—S1—N1—C7	175.5 (6)	O4—S2—N2—C21	−50.1 (8)
C1—S1—N1—C7	−69.4 (7)	C15—S2—N2—C21	66.0 (8)
O2—S1—C1—C6	153.8 (7)	O3—S2—C15—C16	−23.8 (9)
O1—S1—C1—C6	22.4 (9)	O4—S2—C15—C16	−156.4 (8)
N1—S1—C1—C6	−90.5 (8)	N2—S2—C15—C16	88.4 (8)
O2—S1—C1—C2	−30.9 (9)	O3—S2—C15—C20	152.8 (8)
O1—S1—C1—C2	−162.3 (8)	O4—S2—C15—C20	20.2 (9)
N1—S1—C1—C2	84.8 (9)	N2—S2—C15—C20	−95.0 (8)
C6—C1—C2—C3	−1.1 (16)	C20—C15—C16—C17	5.0 (15)
S1—C1—C2—C3	−176.4 (9)	S2—C15—C16—C17	−178.4 (8)
C1—C2—C3—C4	0.8 (19)	C15—C16—C17—C18	−2.1 (17)
C2—C3—C4—C5	−0.9 (19)	C16—C17—C18—C19	0.9 (18)
C2—C3—C4—Cl1	178.0 (10)	C16—C17—C18—Cl2	−179.0 (9)
C3—C4—C5—C6	1.3 (18)	C17—C18—C19—C20	−2.5 (18)
Cl1—C4—C5—C6	−177.5 (9)	Cl2—C18—C19—C20	177.3 (9)
C4—C5—C6—C1	−1.7 (17)	C18—C19—C20—C15	5.4 (17)
C2—C1—C6—C5	1.6 (15)	C16—C15—C20—C19	−6.8 (15)
S1—C1—C6—C5	176.9 (8)	S2—C15—C20—C19	176.5 (9)
S1—N1—C7—C12	−71.4 (10)	S2—N2—C21—C26	62.2 (11)
S1—N1—C7—C8	110.6 (8)	S2—N2—C21—C22	−121.8 (8)
C12—C7—C8—C9	−2.7 (13)	C26—C21—C22—C23	2.1 (13)
N1—C7—C8—C9	175.3 (8)	N2—C21—C22—C23	−173.9 (8)
C7—C8—C9—C10	2.7 (13)	C21—C22—C23—C24	−0.5 (13)
C7—C8—C9—C13	−174.6 (9)	C21—C22—C23—C27	179.1 (8)
C8—C9—C10—C11	−1.5 (14)	C22—C23—C24—C25	−1.2 (14)
C13—C9—C10—C11	175.9 (10)	C27—C23—C24—C25	179.2 (9)
C9—C10—C11—C12	0.2 (15)	C23—C24—C25—C26	1.2 (14)
C9—C10—C11—C14	−177.6 (9)	C23—C24—C25—C28	−179.6 (10)
C10—C11—C12—C7	−0.2 (15)	C22—C21—C26—C25	−2.1 (14)
C14—C11—C12—C7	177.7 (9)	N2—C21—C26—C25	173.8 (8)
C8—C7—C12—C11	1.4 (13)	C24—C25—C26—C21	0.4 (14)
N1—C7—C12—C11	−176.6 (9)	C28—C25—C26—C21	−178.7 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.49	3.001 (9)	119
N2—H2A···O1ⁱⁱ	0.86	2.39	3.006 (9)	130

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO₂S
M_r	295.77
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	21.990 (2), 10.0470 (8), 26.408 (2)
V (Å³)	5834.4 (8)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.40 × 0.20 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.856, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	21403, 5320, 2694
R_int	0.106
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.128, 0.345, 1.07
No. of reflections	5320
No. of parameters	347
No. of restraints	1
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1148P)² + 41.4199P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.41

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.49	3.001 (9)	119.2
N2—H2A···O1ⁱⁱ	0.86	2.39	3.006 (9)	129.5

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

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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