N-(4-Chloro­benzo­yl)-4-methyl­benzene­sulfonamide

Suchetan, P.A.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536809055585

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o327

https://doi.org/10.1107/S1600536809055585

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N-(4-Chlorobenzoyl)-4-methylbenzenesulfonamide

P. A. Suchetan,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^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 23 December 2009; accepted 28 December 2009; online 9 January 2010)

The asymmetric unit of the title compound, C₁₄H₁₂ClNO₃S, contains two independent molecules. The dihedral angles between the two aromatic rings in each molecule are 81.0 (1) and 76.3 (1)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2009a ,b ); Suchetan et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₂ClNO₃S
M_r = 309.76
Monoclinic, C 2/c
a = 25.675 (3) Å
b = 12.0508 (8) Å
c = 22.191 (3) Å
β = 122.16 (1)°
V = 5812.5 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 299 K
0.50 × 0.48 × 0.44 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.821, T_max = 0.840
12864 measured reflections
5931 independent reflections
3733 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.07
5931 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5ⁱ	0.84 (1)	2.35 (1)	3.133 (3)	156 (2)
N2—H2N⋯O2ⁱⁱ	0.87 (1)	2.03 (1)	2.890 (3)	170 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: https://doi.org/10.1107/S1600536809055585/bt5156sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055585/bt5156Isup2.hkl

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of a study of the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2009a,b; Suchetan et al., 2009), in the present work, the structure of N-(4-chlorobenzoyl)4-methylbenzenesulfonamide (I) has been determined (Fig.1). The conformations of the N—H bonds in the C—SO₂—NH—C(O) segments of the structure are anti to the C=O bonds, similar to that observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009a) and N-(4-chlorobenzoyl) benzenesulfonamide (III)(Suchetan et al., 2009).

The molecules are twisted at the S atom with the torsional angles of 67.1 (2)° and 67.7 (2)°, in the two molecules. The dihedral angles between the sulfonyl benzene ring and the —SO₂—NH—C—O segment are 83.6 (1)° and 81.0 (1)°, compared to the values of 86.5(0.1) in (II) and 75.7 (1)° in (III). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings in (I) are 81.0 (1)° and 76.3 (1)°, compared to the values of 80.3(0.1) in (II) and 68.6 (1)° in (III).

The dihedral angle between the sulfonyl benzene rings of the two molecules in the asymmetric unit is 45.8 (1)°. The packing of molecules linked by of N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For background literature and similar structures, see: Gowda et al. (2009a,b); Suchetan et al. (2009).

Experimental top

N-(4-Chlorobenzoyl)4-methylbenzenesulfonamide was prepared by heating a mixture of 4-methylbenzenesulfonamide and 4-chlorobenzoyl chloride at 60° C for one hour. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in sodium hydrogen carbonate solution. The compound was precipitated by acidifying the filtered solution with dil. HCl. It was filtered and dried. The purity of the compound was checked by recording its melting point (168–170° C). Single crystals were obtained from slow evaporation of a solution of the compound in toluene. Prism like colourless single crystals of the title compound were obtained from a slow evaporation of its toluene solution at room temperature and the X-ray diffraction studies were also carried out at room temperature.

Structure description top

For background literature and similar structures, see: Gowda et al. (2009a,b); Suchetan et al. (2009).

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 the displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-(4-Chlorobenzoyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₄H₁₂ClNO₃S	F(000) = 2560
M_r = 309.76	D_x = 1.416 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3720 reflections
a = 25.675 (3) Å	θ = 2.4–27.8°
b = 12.0508 (8) Å	µ = 0.41 mm⁻¹
c = 22.191 (3) Å	T = 299 K
β = 122.16 (1)°	Prism, colourless
V = 5812.5 (11) Å³	0.50 × 0.48 × 0.44 mm
Z = 16

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5931 independent reflections
Radiation source: fine-focus sealed tube	3733 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −25→32
T_min = 0.821, T_max = 0.840	k = −10→15
12864 measured reflections	l = −27→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0686P)² + 0.2769P] where P = (F_o² + 2F_c²)/3
5931 reflections	(Δ/σ)_max < 0.001
367 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO₃S	V = 5812.5 (11) Å³
M_r = 309.76	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 25.675 (3) Å	µ = 0.41 mm⁻¹
b = 12.0508 (8) Å	T = 299 K
c = 22.191 (3) Å	0.50 × 0.48 × 0.44 mm
β = 122.16 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5931 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3733 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.840	R_int = 0.018
12864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.22 e Å⁻³
5931 reflections	Δρ_min = −0.35 e Å⁻³
367 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.38789 (4)	0.05434 (7)	0.38377 (5)	0.0983 (3)
S1	0.14332 (3)	−0.10122 (5)	0.50954 (3)	0.05366 (19)
O1	0.11216 (9)	−0.19893 (15)	0.47163 (12)	0.0881 (6)
O2	0.18104 (8)	−0.10514 (17)	0.58521 (9)	0.0788 (6)
O3	0.22829 (9)	0.08559 (16)	0.54283 (10)	0.0806 (6)
N1	0.18659 (8)	−0.06886 (16)	0.47816 (9)	0.0452 (5)
H1N	0.1773 (10)	−0.1095 (16)	0.4431 (9)	0.054*
C1	0.09034 (10)	0.00583 (18)	0.48616 (12)	0.0442 (5)
C2	0.09089 (11)	0.0707 (2)	0.53769 (14)	0.0585 (7)
H2	0.1209	0.0605	0.5855	0.070*
C3	0.04631 (14)	0.1506 (2)	0.51720 (18)	0.0740 (8)
H3	0.0462	0.1941	0.5518	0.089*
C4	0.00175 (14)	0.1678 (3)	0.4465 (2)	0.0793 (9)
C5	0.00290 (14)	0.1015 (3)	0.39662 (17)	0.0886 (10)
H5	−0.0269	0.1118	0.3487	0.106*
C6	0.04580 (12)	0.0223 (2)	0.41515 (14)	0.0691 (7)
H6	0.0455	−0.0211	0.3803	0.083*
C7	0.22739 (10)	0.01850 (19)	0.50176 (12)	0.0477 (6)
C8	0.26807 (10)	0.02355 (18)	0.47333 (11)	0.0417 (5)
C9	0.28899 (10)	0.12670 (19)	0.46694 (13)	0.0532 (6)
H9	0.2778	0.1901	0.4812	0.064*
C10	0.32578 (11)	0.1362 (2)	0.44001 (13)	0.0566 (7)
H10	0.3397	0.2055	0.4361	0.068*
C11	0.34187 (11)	0.0432 (2)	0.41897 (13)	0.0547 (6)
C12	0.32329 (11)	−0.0603 (2)	0.42626 (13)	0.0580 (7)
H12	0.3360	−0.1233	0.4133	0.070*
C13	0.28596 (10)	−0.06994 (19)	0.45281 (12)	0.0494 (6)
H13	0.2726	−0.1396	0.4570	0.059*
C14	−0.04607 (16)	0.2566 (3)	0.4263 (2)	0.1319 (16)
H14A	−0.0263	0.3246	0.4500	0.158*
H14B	−0.0740	0.2341	0.4402	0.158*
H14C	−0.0684	0.2679	0.3757	0.158*
Cl2	0.10332 (4)	0.14098 (7)	0.31950 (5)	0.0936 (3)
S2	0.33983 (3)	0.23886 (6)	0.17178 (3)	0.0584 (2)
O4	0.31253 (8)	0.18435 (17)	0.10439 (8)	0.0764 (6)
O5	0.35779 (10)	0.35126 (16)	0.17631 (11)	0.0853 (6)
O6	0.33220 (8)	0.33394 (15)	0.29154 (9)	0.0688 (5)
N2	0.28714 (9)	0.22737 (16)	0.19241 (10)	0.0510 (5)
H2N	0.2582 (8)	0.1838 (16)	0.1619 (10)	0.061*
C15	0.40193 (10)	0.1613 (2)	0.23652 (12)	0.0501 (6)
C16	0.39912 (11)	0.0479 (2)	0.23028 (13)	0.0613 (7)
H16	0.3644	0.0142	0.1926	0.074*
C17	0.44735 (13)	−0.0156 (3)	0.27945 (16)	0.0755 (8)
H17	0.4450	−0.0924	0.2745	0.091*
C18	0.49838 (13)	0.0307 (4)	0.33503 (16)	0.0806 (9)
C19	0.50120 (13)	0.1440 (4)	0.34170 (15)	0.0901 (11)
H19	0.5361	0.1766	0.3797	0.108*
C20	0.45307 (13)	0.2109 (3)	0.29301 (14)	0.0734 (8)
H20	0.4552	0.2876	0.2984	0.088*
C21	0.29100 (11)	0.27162 (19)	0.25229 (12)	0.0486 (6)
C22	0.24186 (10)	0.23757 (18)	0.26438 (11)	0.0433 (5)
C23	0.22642 (11)	0.3098 (2)	0.30130 (12)	0.0533 (6)
H23	0.2454	0.3788	0.3154	0.064*
C24	0.18339 (12)	0.2803 (2)	0.31707 (13)	0.0585 (7)
H24	0.1725	0.3296	0.3408	0.070*
C25	0.15648 (11)	0.1773 (2)	0.29750 (13)	0.0555 (6)
C26	0.17150 (12)	0.1034 (2)	0.26192 (13)	0.0576 (6)
H26	0.1531	0.0338	0.2490	0.069*
C27	0.21412 (11)	0.13404 (19)	0.24571 (12)	0.0517 (6)
H27	0.2246	0.0844	0.2218	0.062*
C28	0.55230 (14)	−0.0392 (4)	0.38905 (19)	0.1392 (17)
H28A	0.5748	−0.0653	0.3685	0.167*
H28B	0.5374	−0.1014	0.4026	0.167*
H28C	0.5789	0.0050	0.4303	0.167*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1146 (7)	0.0990 (6)	0.1408 (8)	0.0175 (5)	0.1081 (6)	0.0329 (5)
S1	0.0629 (4)	0.0522 (4)	0.0623 (4)	0.0014 (3)	0.0443 (3)	0.0062 (3)
O1	0.1045 (15)	0.0493 (11)	0.1475 (19)	−0.0261 (11)	0.0920 (15)	−0.0236 (12)
O2	0.0802 (12)	0.1132 (16)	0.0579 (12)	0.0377 (12)	0.0467 (10)	0.0363 (11)
O3	0.0916 (14)	0.0817 (14)	0.0988 (15)	−0.0321 (11)	0.0711 (13)	−0.0506 (12)
N1	0.0521 (11)	0.0500 (12)	0.0439 (11)	−0.0115 (9)	0.0326 (10)	−0.0143 (9)
C1	0.0444 (12)	0.0488 (14)	0.0459 (14)	−0.0055 (10)	0.0283 (11)	0.0032 (10)
C2	0.0564 (15)	0.0642 (17)	0.0577 (16)	−0.0022 (13)	0.0323 (13)	−0.0058 (13)
C3	0.080 (2)	0.0623 (19)	0.107 (3)	0.0012 (16)	0.069 (2)	−0.0054 (17)
C4	0.0615 (18)	0.074 (2)	0.124 (3)	0.0162 (16)	0.064 (2)	0.042 (2)
C5	0.0615 (18)	0.129 (3)	0.074 (2)	0.020 (2)	0.0349 (17)	0.041 (2)
C6	0.0667 (17)	0.091 (2)	0.0517 (17)	0.0017 (16)	0.0326 (14)	0.0052 (15)
C7	0.0526 (14)	0.0490 (14)	0.0448 (14)	−0.0029 (12)	0.0281 (11)	−0.0081 (11)
C8	0.0420 (12)	0.0412 (13)	0.0431 (13)	−0.0006 (10)	0.0233 (10)	−0.0018 (10)
C9	0.0556 (14)	0.0412 (14)	0.0663 (16)	0.0040 (11)	0.0348 (13)	−0.0005 (11)
C10	0.0555 (15)	0.0457 (15)	0.0730 (18)	0.0020 (12)	0.0372 (14)	0.0153 (12)
C11	0.0552 (14)	0.0602 (17)	0.0630 (16)	0.0089 (13)	0.0411 (13)	0.0166 (13)
C12	0.0678 (16)	0.0494 (15)	0.0771 (18)	0.0106 (13)	0.0522 (15)	0.0037 (13)
C13	0.0585 (14)	0.0401 (14)	0.0625 (16)	−0.0003 (11)	0.0408 (13)	0.0012 (11)
C14	0.101 (3)	0.113 (3)	0.227 (5)	0.051 (2)	0.118 (3)	0.081 (3)
Cl2	0.0976 (6)	0.1036 (7)	0.1202 (7)	−0.0049 (5)	0.0852 (6)	0.0033 (5)
S2	0.0639 (4)	0.0694 (5)	0.0533 (4)	−0.0019 (3)	0.0388 (3)	0.0103 (3)
O4	0.0730 (12)	0.1215 (16)	0.0424 (10)	0.0038 (12)	0.0358 (9)	−0.0008 (10)
O5	0.1050 (15)	0.0662 (13)	0.1101 (17)	−0.0067 (11)	0.0744 (14)	0.0229 (11)
O6	0.0759 (12)	0.0704 (12)	0.0660 (12)	−0.0237 (10)	0.0417 (10)	−0.0165 (10)
N2	0.0519 (12)	0.0614 (14)	0.0430 (11)	−0.0046 (10)	0.0275 (10)	−0.0021 (9)
C15	0.0492 (14)	0.0624 (17)	0.0465 (14)	−0.0135 (12)	0.0307 (12)	−0.0030 (12)
C16	0.0503 (15)	0.0705 (19)	0.0578 (17)	−0.0067 (14)	0.0252 (13)	−0.0029 (14)
C17	0.0630 (18)	0.082 (2)	0.080 (2)	0.0059 (16)	0.0372 (18)	0.0178 (17)
C18	0.0546 (18)	0.127 (3)	0.064 (2)	0.000 (2)	0.0343 (16)	0.024 (2)
C19	0.0490 (17)	0.157 (4)	0.0515 (19)	−0.036 (2)	0.0178 (15)	−0.010 (2)
C20	0.0704 (18)	0.087 (2)	0.0611 (18)	−0.0333 (17)	0.0337 (16)	−0.0167 (16)
C21	0.0584 (15)	0.0430 (14)	0.0453 (14)	0.0013 (12)	0.0281 (12)	0.0025 (11)
C22	0.0521 (13)	0.0399 (13)	0.0380 (12)	0.0053 (11)	0.0241 (11)	0.0052 (10)
C23	0.0672 (16)	0.0379 (13)	0.0566 (15)	−0.0008 (12)	0.0341 (13)	−0.0041 (11)
C24	0.0702 (17)	0.0538 (16)	0.0626 (17)	0.0121 (14)	0.0428 (14)	−0.0011 (13)
C25	0.0586 (15)	0.0609 (17)	0.0552 (15)	0.0058 (13)	0.0358 (13)	0.0081 (13)
C26	0.0703 (16)	0.0476 (15)	0.0643 (16)	−0.0079 (13)	0.0421 (14)	−0.0018 (13)
C27	0.0667 (16)	0.0457 (14)	0.0510 (15)	0.0020 (12)	0.0369 (13)	−0.0026 (11)
C28	0.069 (2)	0.233 (5)	0.096 (3)	0.032 (3)	0.030 (2)	0.081 (3)

Geometric parameters (Å, º) top

Cl1—C11	1.734 (2)	Cl2—C25	1.732 (2)
S1—O1	1.4205 (19)	S2—O5	1.4170 (19)
S1—O2	1.4242 (18)	S2—O4	1.4294 (18)
S1—N1	1.6417 (18)	S2—N2	1.6487 (19)
S1—C1	1.741 (2)	S2—C15	1.744 (2)
O3—C7	1.209 (2)	O6—C21	1.209 (3)
N1—C7	1.377 (3)	N2—C21	1.385 (3)
N1—H1N	0.838 (9)	N2—H2N	0.867 (9)
C1—C2	1.379 (3)	C15—C16	1.371 (3)
C1—C6	1.383 (3)	C15—C20	1.378 (3)
C2—C3	1.375 (3)	C16—C17	1.368 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.380 (4)	C17—C18	1.352 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.377 (5)	C18—C19	1.371 (4)
C4—C14	1.507 (4)	C18—C28	1.515 (4)
C5—C6	1.345 (4)	C19—C20	1.387 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.481 (3)	C21—C22	1.481 (3)
C8—C13	1.382 (3)	C22—C27	1.386 (3)
C8—C9	1.391 (3)	C22—C23	1.390 (3)
C9—C10	1.365 (3)	C23—C24	1.372 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.361 (3)	C24—C25	1.374 (3)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.375 (3)	C25—C26	1.374 (3)
C12—C13	1.371 (3)	C26—C27	1.372 (3)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600

O1—S1—O2	119.07 (13)	O5—S2—O4	118.25 (12)
O1—S1—N1	103.93 (10)	O5—S2—N2	110.16 (11)
O2—S1—N1	108.60 (10)	O4—S2—N2	103.53 (10)
O1—S1—C1	109.47 (12)	O5—S2—C15	109.49 (12)
O2—S1—C1	108.00 (11)	O4—S2—C15	109.86 (12)
N1—S1—C1	107.18 (10)	N2—S2—C15	104.58 (10)
C7—N1—S1	124.74 (15)	C21—N2—S2	125.70 (17)
C7—N1—H1N	125.6 (16)	C21—N2—H2N	125.2 (16)
S1—N1—H1N	109.4 (16)	S2—N2—H2N	108.9 (16)
C2—C1—C6	120.0 (2)	C16—C15—C20	119.8 (3)
C2—C1—S1	120.74 (19)	C16—C15—S2	118.36 (18)
C6—C1—S1	119.16 (19)	C20—C15—S2	121.8 (2)
C3—C2—C1	118.9 (3)	C17—C16—C15	120.0 (3)
C3—C2—H2	120.5	C17—C16—H16	120.0
C1—C2—H2	120.5	C15—C16—H16	120.0
C2—C3—C4	121.4 (3)	C18—C17—C16	121.5 (3)
C2—C3—H3	119.3	C18—C17—H17	119.2
C4—C3—H3	119.3	C16—C17—H17	119.2
C5—C4—C3	117.9 (3)	C17—C18—C19	118.6 (3)
C5—C4—C14	122.4 (4)	C17—C18—C28	121.8 (4)
C3—C4—C14	119.7 (4)	C19—C18—C28	119.6 (3)
C6—C5—C4	122.0 (3)	C18—C19—C20	121.4 (3)
C6—C5—H5	119.0	C18—C19—H19	119.3
C4—C5—H5	119.0	C20—C19—H19	119.3
C5—C6—C1	119.8 (3)	C15—C20—C19	118.6 (3)
C5—C6—H6	120.1	C15—C20—H20	120.7
C1—C6—H6	120.1	C19—C20—H20	120.7
O3—C7—N1	120.2 (2)	O6—C21—N2	121.2 (2)
O3—C7—C8	124.0 (2)	O6—C21—C22	123.0 (2)
N1—C7—C8	115.83 (18)	N2—C21—C22	115.7 (2)
C13—C8—C9	118.7 (2)	C27—C22—C23	118.5 (2)
C13—C8—C7	122.7 (2)	C27—C22—C21	123.2 (2)
C9—C8—C7	118.6 (2)	C23—C22—C21	118.1 (2)
C10—C9—C8	121.0 (2)	C24—C23—C22	120.6 (2)
C10—C9—H9	119.5	C24—C23—H23	119.7
C8—C9—H9	119.5	C22—C23—H23	119.7
C11—C10—C9	119.2 (2)	C23—C24—C25	119.4 (2)
C11—C10—H10	120.4	C23—C24—H24	120.3
C9—C10—H10	120.4	C25—C24—H24	120.3
C10—C11—C12	121.3 (2)	C26—C25—C24	121.3 (2)
C10—C11—Cl1	119.64 (19)	C26—C25—Cl2	120.2 (2)
C12—C11—Cl1	119.06 (19)	C24—C25—Cl2	118.56 (19)
C13—C12—C11	119.5 (2)	C27—C26—C25	118.9 (2)
C13—C12—H12	120.2	C27—C26—H26	120.5
C11—C12—H12	120.2	C25—C26—H26	120.5
C12—C13—C8	120.2 (2)	C26—C27—C22	121.2 (2)
C12—C13—H13	119.9	C26—C27—H27	119.4
C8—C13—H13	119.9	C22—C27—H27	119.4
C4—C14—H14A	109.5	C18—C28—H28A	109.5
C4—C14—H14B	109.5	C18—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C4—C14—H14C	109.5	C18—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

O1—S1—N1—C7	−177.1 (2)	O5—S2—N2—C21	−49.9 (2)
O2—S1—N1—C7	−49.4 (2)	O4—S2—N2—C21	−177.2 (2)
C1—S1—N1—C7	67.1 (2)	C15—S2—N2—C21	67.7 (2)
O1—S1—C1—C2	132.2 (2)	O5—S2—C15—C16	−164.32 (18)
O2—S1—C1—C2	1.2 (2)	O4—S2—C15—C16	−32.9 (2)
N1—S1—C1—C2	−115.67 (19)	N2—S2—C15—C16	77.7 (2)
O1—S1—C1—C6	−45.1 (2)	O5—S2—C15—C20	15.6 (2)
O2—S1—C1—C6	−176.12 (19)	O4—S2—C15—C20	147.08 (19)
N1—S1—C1—C6	67.0 (2)	N2—S2—C15—C20	−102.4 (2)
C6—C1—C2—C3	0.6 (4)	C20—C15—C16—C17	−1.0 (4)
S1—C1—C2—C3	−176.69 (19)	S2—C15—C16—C17	179.0 (2)
C1—C2—C3—C4	−0.7 (4)	C15—C16—C17—C18	0.3 (4)
C2—C3—C4—C5	0.5 (4)	C16—C17—C18—C19	0.1 (4)
C2—C3—C4—C14	−179.7 (2)	C16—C17—C18—C28	−179.1 (3)
C3—C4—C5—C6	−0.2 (4)	C17—C18—C19—C20	0.2 (5)
C14—C4—C5—C6	180.0 (3)	C28—C18—C19—C20	179.4 (3)
C4—C5—C6—C1	0.1 (4)	C16—C15—C20—C19	1.2 (4)
C2—C1—C6—C5	−0.3 (4)	S2—C15—C20—C19	−178.8 (2)
S1—C1—C6—C5	177.0 (2)	C18—C19—C20—C15	−0.8 (4)
S1—N1—C7—O3	−8.7 (3)	S2—N2—C21—O6	8.0 (3)
S1—N1—C7—C8	171.77 (16)	S2—N2—C21—C22	−172.02 (15)
O3—C7—C8—C13	151.8 (3)	O6—C21—C22—C27	−147.2 (2)
N1—C7—C8—C13	−28.6 (3)	N2—C21—C22—C27	32.8 (3)
O3—C7—C8—C9	−28.3 (4)	O6—C21—C22—C23	27.5 (3)
N1—C7—C8—C9	151.2 (2)	N2—C21—C22—C23	−152.5 (2)
C13—C8—C9—C10	0.9 (3)	C27—C22—C23—C24	−1.8 (3)
C7—C8—C9—C10	−179.0 (2)	C21—C22—C23—C24	−176.8 (2)
C8—C9—C10—C11	0.2 (4)	C22—C23—C24—C25	1.5 (4)
C9—C10—C11—C12	−1.9 (4)	C23—C24—C25—C26	−0.5 (4)
C9—C10—C11—Cl1	179.30 (18)	C23—C24—C25—Cl2	178.81 (18)
C10—C11—C12—C13	2.4 (4)	C24—C25—C26—C27	−0.2 (4)
Cl1—C11—C12—C13	−178.81 (18)	Cl2—C25—C26—C27	−179.45 (17)
C11—C12—C13—C8	−1.2 (4)	C25—C26—C27—C22	−0.2 (4)
C9—C8—C13—C12	−0.4 (3)	C23—C22—C27—C26	1.2 (3)
C7—C8—C13—C12	179.4 (2)	C21—C22—C27—C26	175.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5ⁱ	0.84 (1)	2.35 (1)	3.133 (3)	156 (2)
N2—H2N···O2ⁱⁱ	0.87 (1)	2.03 (1)	2.890 (3)	170 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₃S
M_r	309.76
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	25.675 (3), 12.0508 (8), 22.191 (3)
β (°)	122.16 (1)
V (Å³)	5812.5 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.50 × 0.48 × 0.44

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.821, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	12864, 5931, 3733
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.07
No. of reflections	5931
No. of parameters	367
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.35

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—H1N···O5ⁱ	0.838 (9)	2.349 (13)	3.133 (3)	156 (2)
N2—H2N···O2ⁱⁱ	0.867 (9)	2.032 (11)	2.890 (3)	170 (2)

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

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009a). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009b). Acta Cryst. E65, o2750. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
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
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3156. Web of Science CSD CrossRef IUCr Journals Google Scholar