N-Benzoyl-4-chloro­benzene­sulfonamide

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

doi:10.1107/S160053681000783X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o766

doi:10.1107/S160053681000783X

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N-Benzoyl-4-chlorobenzenesulfonamide

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 22 February 2010; accepted 1 March 2010; online 6 March 2010)

The asymmetric unit of the title compound, C₁₃H₁₀ClNO₃S, contains two independent molecules. The molecules have C—S—N—C torsion angles of −70.0 (2) and 61.3 (2)° for molecules 1 and 2, respectively. The dihedral angles between the sulfonyl benzene rings and the –SO₂—NH—C—O segments are 72.0 (1) and 77.3 (1)° for molecules 1 and 2, respectively, and the dihedral angles between the sulfonyl and the benzoyl benzene rings are 62.8 (1) and 78.6 (1)°, respectively. In the crystal, molecules 1 and 2 are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009 ; 2010 ); Suchetan et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₀ClNO₃S
M_r = 295.73
Triclinic, $[P \overline 1]$
a = 9.138 (1) Å
b = 12.026 (2) Å
c = 12.512 (2) Å
α = 91.15 (1)°
β = 93.53 (1)°
γ = 107.40 (2)°
V = 1308.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 4.12 mm⁻¹
T = 299 K
0.50 × 0.40 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan North et al., 1968 T_min = 0.233, T_max = 0.290
9165 measured reflections
4655 independent reflections
3966 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 120 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.05
4655 reflections
350 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.84 (2)	2.16 (2)	2.967 (3)	161 (3)
N2—H2N⋯O4ⁱⁱ	0.83 (2)	2.15 (2)	2.962 (3)	164 (3)
Symmetry codes: (i) -x, -y, -z; (ii) -x, -y+1, -z+1.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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/S160053681000783X/fk2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000783X/fk2014Isup2.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 a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2009; 2010; Suchetan et al., 2009), the structure of N-(benzoyl)4-chlorobenzenesulfonamide (I) has been determined. The asymmetric unit of the structure contains two independent molecules (Fig.1). The conformations of the N—H bonds in the C—SO₂—NH—C(O) segments are anti to the C=O bonds, similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(benzoyl)2-chlorobenzenesulfonamide (III) (Gowda et al., 2010) and N-(4-chlorobenzoyl)benzenesulfonamide (IV)(Suchetan et al., 2009).

The molecules are twisted at the S atoms with the torsional angles of -70.0 (2)° and 61.3 (2)° in the two independent molecules. The dihedral angles between the sulfonyl benzene rings and the —SO₂—NH—C—O segments are 72.0 (1)° (molecule 1) and 77.3 (1)° (molecule 2), compared to the values of 86.5 (1) in (II), 87.3 (1)° in (III) and 75.7 (1)° in (IV). Furthermore, the dihedral angles between the benzene rings are 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2), compared to the values of 80.3 (1) in (II), 73.3 (1)° in (III) and 68.6 (1)° in (IV). The packing of molecules linked by N—H···O(S) hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

Experimental top

The title compound was prepared by refluxing a mixture of benzoic acid, 4-chlorobenzenesulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid, N-(benzoyl)4-chlorobenzenesulfonamide obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried compound was recrystallized to the constant melting point.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown from a slow evaporation of its toluene solution at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

N-Benzoyl-4-chlorobenzenesulfonamide top

Crystal data top

C₁₃H₁₀ClNO₃S	Z = 4
M_r = 295.73	F(000) = 608
Triclinic, P1	D_x = 1.501 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 9.138 (1) Å	Cell parameters from 25 reflections
b = 12.026 (2) Å	θ = 6.3–20.7°
c = 12.512 (2) Å	µ = 4.12 mm⁻¹
α = 91.15 (1)°	T = 299 K
β = 93.53 (1)°	Prism, colourless
γ = 107.40 (2)°	0.50 × 0.40 × 0.40 mm
V = 1308.5 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	3966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 67.0°, θ_min = 3.5°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan North et al., 1968	k = −14→14
T_min = 0.233, T_max = 0.290	l = −14→14
9165 measured reflections	3 standard reflections every 120 min
4655 independent reflections	intensity decay: 2.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0517P)² + 0.515P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4655 reflections	Δρ_max = 0.34 e Å⁻³
350 parameters	Δρ_min = −0.34 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (5)

Crystal data top

C₁₃H₁₀ClNO₃S	γ = 107.40 (2)°
M_r = 295.73	V = 1308.5 (3) Å³
Triclinic, P1	Z = 4
a = 9.138 (1) Å	Cu Kα radiation
b = 12.026 (2) Å	µ = 4.12 mm⁻¹
c = 12.512 (2) Å	T = 299 K
α = 91.15 (1)°	0.50 × 0.40 × 0.40 mm
β = 93.53 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3966 reflections with I > 2σ(I)
Absorption correction: ψ scan North et al., 1968	R_int = 0.044
T_min = 0.233, T_max = 0.290	3 standard reflections every 120 min
9165 measured reflections	intensity decay: 2.0%
4655 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.34 e Å⁻³
4655 reflections	Δρ_min = −0.34 e Å⁻³
350 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 > 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	0.13114 (11)	0.65487 (7)	0.19920 (7)	0.0951 (3)
S1	0.12434 (7)	0.19435 (5)	−0.03688 (6)	0.0571 (2)
O1	−0.02885 (19)	0.11806 (14)	−0.03785 (19)	0.0766 (6)
O2	0.1928 (2)	0.22241 (16)	−0.13596 (16)	0.0727 (5)
O3	0.45459 (19)	0.26268 (14)	0.02647 (17)	0.0689 (5)
N1	0.2241 (2)	0.12840 (16)	0.03850 (19)	0.0566 (5)
H1N	0.172 (3)	0.0617 (17)	0.054 (2)	0.068*
C1	0.1337 (2)	0.32370 (18)	0.0343 (2)	0.0515 (5)
C2	0.0252 (3)	0.3229 (2)	0.1058 (2)	0.0633 (7)
H2	−0.0481	0.2532	0.1196	0.076*
C3	0.0251 (3)	0.4250 (2)	0.1567 (2)	0.0696 (7)
H3	−0.0484	0.4255	0.2047	0.084*
C4	0.1352 (3)	0.5262 (2)	0.1355 (2)	0.0625 (6)
C5	0.2456 (3)	0.5282 (2)	0.0662 (2)	0.0629 (7)
H5	0.3200	0.5980	0.0543	0.075*
C6	0.2461 (3)	0.42605 (19)	0.0140 (2)	0.0574 (6)
H6	0.3202	0.4259	−0.0337	0.069*
C7	0.3829 (2)	0.16862 (19)	0.0569 (2)	0.0520 (5)
C8	0.4541 (2)	0.09067 (19)	0.11647 (19)	0.0491 (5)
C9	0.6099 (3)	0.1097 (2)	0.1104 (2)	0.0653 (7)
H9	0.6662	0.1704	0.0708	0.078*
C10	0.6821 (3)	0.0392 (3)	0.1626 (3)	0.0761 (8)
H10	0.7867	0.0516	0.1570	0.091*
C11	0.6022 (3)	−0.0483 (2)	0.2222 (3)	0.0710 (7)
H11	0.6523	−0.0952	0.2577	0.085*
C12	0.4478 (3)	−0.0677 (3)	0.2304 (3)	0.0768 (8)
H12	0.3932	−0.1272	0.2719	0.092*
C13	0.3737 (3)	0.0014 (2)	0.1767 (2)	0.0667 (7)
H13	0.2685	−0.0125	0.1813	0.080*
Cl2	0.09586 (10)	1.12238 (7)	0.31722 (8)	0.0928 (3)
S2	0.15335 (8)	0.68980 (5)	0.55894 (6)	0.0660 (2)
O4	0.0012 (2)	0.61359 (16)	0.5643 (2)	0.0871 (7)
O5	0.2464 (3)	0.72946 (19)	0.65492 (17)	0.0895 (7)
O6	0.4541 (2)	0.75873 (16)	0.47147 (19)	0.0794 (6)
N2	0.2341 (3)	0.61526 (18)	0.48162 (19)	0.0623 (5)
H2N	0.171 (3)	0.5535 (19)	0.456 (2)	0.075*
C14	0.1436 (3)	0.81131 (19)	0.4870 (2)	0.0544 (6)
C15	0.0225 (3)	0.7997 (2)	0.4114 (2)	0.0640 (7)
H15	−0.0496	0.7272	0.3963	0.077*
C16	0.0090 (3)	0.8952 (2)	0.3589 (2)	0.0675 (7)
H16	−0.0714	0.8881	0.3073	0.081*
C17	0.1157 (3)	1.0018 (2)	0.3832 (2)	0.0605 (6)
C18	0.2376 (3)	1.0149 (2)	0.4571 (2)	0.0645 (7)
H18	0.3097	1.0876	0.4713	0.077*
C19	0.2515 (3)	0.9182 (2)	0.5102 (2)	0.0602 (6)
H19	0.3328	0.9253	0.5610	0.072*
C20	0.3804 (3)	0.6593 (2)	0.4480 (2)	0.0595 (6)
C21	0.4389 (3)	0.5793 (2)	0.3827 (2)	0.0550 (6)
C22	0.3646 (3)	0.4623 (2)	0.3640 (3)	0.0712 (7)
H22	0.2712	0.4285	0.3932	0.085*
C23	0.4278 (4)	0.3951 (3)	0.3022 (3)	0.0816 (9)
H23	0.3760	0.3163	0.2896	0.098*
C24	0.5657 (3)	0.4427 (3)	0.2590 (3)	0.0744 (8)
H24	0.6075	0.3966	0.2173	0.089*
C25	0.6410 (4)	0.5582 (3)	0.2777 (3)	0.0829 (9)
H25	0.7353	0.5911	0.2493	0.100*
C26	0.5780 (3)	0.6261 (2)	0.3385 (3)	0.0782 (8)
H26	0.6299	0.7051	0.3502	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1252 (7)	0.0788 (5)	0.0934 (6)	0.0542 (5)	−0.0124 (5)	−0.0192 (4)
S1	0.0512 (3)	0.0391 (3)	0.0765 (4)	0.0097 (2)	−0.0101 (3)	0.0026 (2)
O1	0.0526 (9)	0.0425 (8)	0.1251 (18)	0.0060 (7)	−0.0250 (10)	0.0046 (9)
O2	0.0922 (13)	0.0609 (10)	0.0653 (12)	0.0257 (9)	−0.0039 (10)	−0.0025 (9)
O3	0.0507 (9)	0.0505 (9)	0.0989 (15)	0.0043 (7)	0.0056 (9)	0.0139 (9)
N1	0.0419 (9)	0.0415 (9)	0.0829 (15)	0.0082 (8)	−0.0021 (9)	0.0104 (9)
C1	0.0470 (11)	0.0416 (11)	0.0643 (15)	0.0114 (9)	−0.0012 (10)	0.0077 (10)
C2	0.0514 (13)	0.0562 (14)	0.0809 (19)	0.0114 (10)	0.0121 (12)	0.0204 (12)
C3	0.0690 (16)	0.0765 (17)	0.0723 (18)	0.0323 (14)	0.0171 (14)	0.0148 (14)
C4	0.0729 (16)	0.0553 (13)	0.0631 (16)	0.0277 (12)	−0.0078 (13)	0.0007 (11)
C5	0.0656 (15)	0.0402 (12)	0.0769 (18)	0.0068 (10)	0.0027 (13)	0.0069 (11)
C6	0.0552 (13)	0.0447 (12)	0.0689 (16)	0.0082 (10)	0.0109 (12)	0.0075 (11)
C7	0.0431 (11)	0.0459 (12)	0.0637 (15)	0.0089 (9)	0.0024 (10)	−0.0040 (10)
C8	0.0419 (11)	0.0478 (11)	0.0555 (14)	0.0112 (9)	0.0009 (9)	−0.0070 (9)
C9	0.0425 (12)	0.0564 (14)	0.092 (2)	0.0087 (10)	0.0021 (12)	0.0037 (13)
C10	0.0430 (12)	0.0755 (17)	0.110 (3)	0.0201 (12)	−0.0022 (14)	0.0012 (16)
C11	0.0653 (16)	0.0690 (16)	0.082 (2)	0.0296 (13)	−0.0142 (14)	−0.0009 (14)
C12	0.0683 (17)	0.0810 (18)	0.082 (2)	0.0226 (14)	0.0032 (15)	0.0251 (15)
C13	0.0474 (12)	0.0766 (17)	0.0776 (19)	0.0194 (12)	0.0079 (12)	0.0196 (14)
Cl2	0.1041 (6)	0.0891 (5)	0.1031 (7)	0.0515 (5)	0.0222 (5)	0.0280 (4)
S2	0.0791 (4)	0.0521 (3)	0.0653 (4)	0.0152 (3)	0.0167 (3)	0.0026 (3)
O4	0.0882 (14)	0.0571 (10)	0.1117 (17)	0.0069 (10)	0.0492 (13)	0.0039 (10)
O5	0.1332 (19)	0.0795 (13)	0.0582 (12)	0.0377 (13)	−0.0030 (12)	−0.0003 (10)
O6	0.0592 (10)	0.0560 (10)	0.1145 (17)	0.0062 (8)	0.0011 (11)	−0.0095 (10)
N2	0.0630 (12)	0.0497 (11)	0.0712 (15)	0.0112 (9)	0.0106 (11)	−0.0010 (10)
C14	0.0524 (12)	0.0488 (12)	0.0573 (14)	0.0079 (10)	0.0075 (10)	−0.0066 (10)
C15	0.0537 (13)	0.0574 (14)	0.0719 (18)	0.0057 (11)	−0.0020 (12)	−0.0157 (12)
C16	0.0584 (14)	0.0792 (18)	0.0644 (17)	0.0228 (13)	−0.0065 (12)	−0.0102 (13)
C17	0.0597 (14)	0.0617 (14)	0.0651 (16)	0.0240 (11)	0.0123 (12)	0.0038 (12)
C18	0.0587 (14)	0.0476 (13)	0.0794 (18)	0.0046 (10)	0.0034 (13)	−0.0032 (12)
C19	0.0509 (12)	0.0560 (13)	0.0666 (16)	0.0079 (10)	−0.0058 (11)	−0.0064 (11)
C20	0.0540 (13)	0.0533 (13)	0.0672 (16)	0.0113 (11)	−0.0038 (12)	0.0062 (11)
C21	0.0512 (12)	0.0522 (12)	0.0601 (15)	0.0141 (10)	−0.0022 (11)	0.0103 (10)
C22	0.0571 (14)	0.0602 (15)	0.094 (2)	0.0124 (12)	0.0125 (14)	0.0022 (14)
C23	0.0749 (18)	0.0602 (16)	0.107 (3)	0.0148 (14)	0.0140 (17)	−0.0050 (15)
C24	0.0730 (17)	0.0806 (19)	0.075 (2)	0.0314 (15)	0.0052 (15)	0.0013 (15)
C25	0.0692 (17)	0.082 (2)	0.096 (2)	0.0165 (15)	0.0253 (17)	0.0109 (17)
C26	0.0694 (17)	0.0589 (15)	0.100 (2)	0.0066 (13)	0.0172 (16)	0.0088 (15)

Geometric parameters (Å, º) top

Cl1—C4	1.737 (3)	Cl2—C17	1.734 (3)
S1—O2	1.424 (2)	S2—O5	1.415 (2)
S1—O1	1.4251 (18)	S2—O4	1.425 (2)
S1—N1	1.645 (2)	S2—N2	1.653 (2)
S1—C1	1.753 (2)	S2—C14	1.753 (3)
O3—C7	1.208 (3)	O6—C20	1.204 (3)
N1—C7	1.388 (3)	N2—C20	1.378 (3)
N1—H1N	0.836 (17)	N2—H2N	0.834 (17)
C1—C2	1.374 (4)	C14—C19	1.379 (3)
C1—C6	1.387 (3)	C14—C15	1.383 (4)
C2—C3	1.373 (4)	C15—C16	1.368 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.370 (4)	C16—C17	1.373 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.365 (4)	C17—C18	1.372 (4)
C5—C6	1.382 (3)	C18—C19	1.386 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.480 (3)	C20—C21	1.486 (4)
C8—C13	1.375 (3)	C21—C22	1.375 (4)
C8—C9	1.380 (3)	C21—C26	1.381 (4)
C9—C10	1.372 (4)	C22—C23	1.376 (4)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.355 (4)	C23—C24	1.368 (4)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.370 (4)	C24—C25	1.361 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.379 (4)	C25—C26	1.375 (4)
C12—H12	0.9300	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300

O2—S1—O1	119.10 (13)	O5—S2—O4	119.32 (15)
O2—S1—N1	110.02 (12)	O5—S2—N2	110.30 (14)
O1—S1—N1	103.39 (10)	O4—S2—N2	103.33 (12)
O2—S1—C1	109.16 (11)	O5—S2—C14	108.61 (12)
O1—S1—C1	108.42 (12)	O4—S2—C14	108.37 (13)
N1—S1—C1	105.90 (11)	N2—S2—C14	106.11 (12)
C7—N1—S1	123.68 (17)	C20—N2—S2	123.63 (18)
C7—N1—H1N	122.9 (19)	C20—N2—H2N	123 (2)
S1—N1—H1N	112.3 (19)	S2—N2—H2N	112 (2)
C2—C1—C6	121.1 (2)	C19—C14—C15	120.8 (2)
C2—C1—S1	119.31 (18)	C19—C14—S2	119.9 (2)
C6—C1—S1	119.5 (2)	C15—C14—S2	119.27 (18)
C3—C2—C1	119.9 (2)	C16—C15—C14	119.8 (2)
C3—C2—H2	120.1	C16—C15—H15	120.1
C1—C2—H2	120.1	C14—C15—H15	120.1
C4—C3—C2	118.9 (3)	C15—C16—C17	119.2 (2)
C4—C3—H3	120.6	C15—C16—H16	120.4
C2—C3—H3	120.6	C17—C16—H16	120.4
C5—C4—C3	122.0 (3)	C18—C17—C16	121.9 (2)
C5—C4—Cl1	119.9 (2)	C18—C17—Cl2	119.4 (2)
C3—C4—Cl1	118.1 (2)	C16—C17—Cl2	118.7 (2)
C4—C5—C6	119.6 (2)	C17—C18—C19	118.9 (2)
C4—C5—H5	120.2	C17—C18—H18	120.5
C6—C5—H5	120.2	C19—C18—H18	120.5
C5—C6—C1	118.5 (2)	C14—C19—C18	119.3 (2)
C5—C6—H6	120.7	C14—C19—H19	120.3
C1—C6—H6	120.7	C18—C19—H19	120.3
O3—C7—N1	120.4 (2)	O6—C20—N2	119.9 (3)
O3—C7—C8	123.8 (2)	O6—C20—C21	123.1 (2)
N1—C7—C8	115.85 (19)	N2—C20—C21	117.0 (2)
C13—C8—C9	118.9 (2)	C22—C21—C26	118.1 (3)
C13—C8—C7	123.6 (2)	C22—C21—C20	124.5 (2)
C9—C8—C7	117.5 (2)	C26—C21—C20	117.4 (2)
C10—C9—C8	120.2 (3)	C21—C22—C23	120.3 (3)
C10—C9—H9	119.9	C21—C22—H22	119.8
C8—C9—H9	119.9	C23—C22—H22	119.8
C11—C10—C9	120.6 (2)	C24—C23—C22	120.9 (3)
C11—C10—H10	119.7	C24—C23—H23	119.5
C9—C10—H10	119.7	C22—C23—H23	119.5
C10—C11—C12	120.1 (3)	C25—C24—C23	119.3 (3)
C10—C11—H11	119.9	C25—C24—H24	120.4
C12—C11—H11	119.9	C23—C24—H24	120.4
C11—C12—C13	119.8 (3)	C24—C25—C26	120.1 (3)
C11—C12—H12	120.1	C24—C25—H25	119.9
C13—C12—H12	120.1	C26—C25—H25	119.9
C8—C13—C12	120.4 (2)	C25—C26—C21	121.2 (3)
C8—C13—H13	119.8	C25—C26—H26	119.4
C12—C13—H13	119.8	C21—C26—H26	119.4

O2—S1—N1—C7	47.9 (2)	O5—S2—N2—C20	−56.1 (3)
O1—S1—N1—C7	176.1 (2)	O4—S2—N2—C20	175.3 (2)
C1—S1—N1—C7	−70.0 (2)	C14—S2—N2—C20	61.3 (2)
O2—S1—C1—C2	152.8 (2)	O5—S2—C14—C19	18.5 (3)
O1—S1—C1—C2	21.6 (2)	O4—S2—C14—C19	149.5 (2)
N1—S1—C1—C2	−88.8 (2)	N2—S2—C14—C19	−100.1 (2)
O2—S1—C1—C6	−24.3 (2)	O5—S2—C14—C15	−158.2 (2)
O1—S1—C1—C6	−155.5 (2)	O4—S2—C14—C15	−27.2 (2)
N1—S1—C1—C6	94.1 (2)	N2—S2—C14—C15	83.3 (2)
C6—C1—C2—C3	1.4 (4)	C19—C14—C15—C16	−0.1 (4)
S1—C1—C2—C3	−175.7 (2)	S2—C14—C15—C16	176.5 (2)
C1—C2—C3—C4	−0.6 (4)	C14—C15—C16—C17	−0.7 (4)
C2—C3—C4—C5	−0.6 (4)	C15—C16—C17—C18	1.5 (4)
C2—C3—C4—Cl1	179.0 (2)	C15—C16—C17—Cl2	−179.2 (2)
C3—C4—C5—C6	1.1 (4)	C16—C17—C18—C19	−1.3 (4)
Cl1—C4—C5—C6	−178.5 (2)	Cl2—C17—C18—C19	179.3 (2)
C4—C5—C6—C1	−0.3 (4)	C15—C14—C19—C18	0.2 (4)
C2—C1—C6—C5	−0.9 (4)	S2—C14—C19—C18	−176.4 (2)
S1—C1—C6—C5	176.14 (19)	C17—C18—C19—C14	0.5 (4)
S1—N1—C7—O3	7.9 (4)	S2—N2—C20—O6	−3.1 (4)
S1—N1—C7—C8	−173.19 (17)	S2—N2—C20—C21	177.37 (18)
O3—C7—C8—C13	160.9 (3)	O6—C20—C21—C22	172.9 (3)
N1—C7—C8—C13	−18.0 (4)	N2—C20—C21—C22	−7.6 (4)
O3—C7—C8—C9	−19.1 (4)	O6—C20—C21—C26	−6.7 (4)
N1—C7—C8—C9	162.0 (2)	N2—C20—C21—C26	172.9 (2)
C13—C8—C9—C10	0.9 (4)	C26—C21—C22—C23	−0.5 (4)
C7—C8—C9—C10	−179.0 (3)	C20—C21—C22—C23	179.9 (3)
C8—C9—C10—C11	−1.3 (5)	C21—C22—C23—C24	0.6 (5)
C9—C10—C11—C12	0.5 (5)	C22—C23—C24—C25	0.0 (5)
C10—C11—C12—C13	0.7 (5)	C23—C24—C25—C26	−0.6 (5)
C9—C8—C13—C12	0.2 (4)	C24—C25—C26—C21	0.7 (5)
C7—C8—C13—C12	−179.8 (3)	C22—C21—C26—C25	−0.1 (5)
C11—C12—C13—C8	−1.0 (5)	C20—C21—C26—C25	179.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.16 (2)	2.967 (3)	161 (3)
N2—H2N···O4ⁱⁱ	0.83 (2)	2.15 (2)	2.962 (3)	164 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO₃S
M_r	295.73
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	9.138 (1), 12.026 (2), 12.512 (2)
α, β, γ (°)	91.15 (1), 93.53 (1), 107.40 (2)
V (Å³)	1308.5 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.12
Crystal size (mm)	0.50 × 0.40 × 0.40

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan North et al., 1968
T_min, T_max	0.233, 0.290
No. of measured, independent and observed [I > 2σ(I)] reflections	9165, 4655, 3966
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.125, 1.05
No. of reflections	4655
No. of parameters	350
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)	0.34, −0.34

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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···O1ⁱ	0.836 (17)	2.164 (19)	2.967 (3)	161 (3)
N2—H2N···O4ⁱⁱ	0.834 (17)	2.150 (19)	2.962 (3)	164 (3)

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

Acknowledgements

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

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794. Web of Science CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science 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
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. 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