N-(2,3-Dichloro­phen­yl)-4-methyl­benzene­sulfonamide

Shakuntala, K.; Foro, S.; Gowda, B.T.; Nirmala, P.G.; Fuess, H.

doi:10.1107/S1600536810044375

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3062

https://doi.org/10.1107/S1600536810044375

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N-(2,3-Dichlorophenyl)-4-methylbenzenesulfonamide

K. Shakuntala,^a Sabine Foro,^b B. Thimme Gowda,^a ^* P. G. Nirmala ^a 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 29 October 2010; accepted 29 October 2010; online 6 November 2010)

The title compound, C₁₃H₁₁Cl₂NO₂S, contains two molecules in the asymmetric unit in which the dihedral angles between the benzene rings are 76.0 (1) and 79.9 (1)°. The conformations of the N—H bonds with respect to their adjacent ortho-chlorine atoms are syn. In the crystal, N—H⋯O hydrogen bonds link the molecules into dimers.

Related literature

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009 , 2010a ,b ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₁Cl₂NO₂S
M_r = 316.19
Monoclinic, P 2₁ /n
a = 14.035 (3) Å
b = 12.386 (2) Å
c = 15.993 (3) Å
β = 98.30 (1)°
V = 2751.1 (9) Å³
Z = 8
Cu Kα radiation
μ = 5.64 mm⁻¹
T = 299 K
0.50 × 0.45 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
9784 measured reflections
4903 independent reflections
4359 reflections with I > 2σ(I)
R_int = 0.131
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.176
S = 1.11
4903 reflections
352 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.84 (2)	2.29 (2)	3.086 (3)	160 (3)
N2—H2N⋯O2	0.85 (2)	2.32 (2)	3.104 (3)	154 (3)

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: https://doi.org/10.1107/S1600536810044375/bq2248sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044375/bq2248Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009; 2010a, b), in the present work, the structure of 4-methyl-N-(2,3-dichlorophenyl)- benzenesulfonamide (I) has been determined. The asymmetric unit of (I) contains two independent molecules. In one of the molecules, conformation of the N—C bond in the C—SO₂—NH—C segment of the structure has gauche torsions with respect to the S═O bonds (Fig. 1). The molecules are bent at the S atoms with the C—SO₂—NH—C torsion angles of 65.4 (2) and -61.7 (2). The conformations of the N—H bonds and the ortho-chloro groups in the anilino benzene rings are syn to each other. The benzene rings in the title compound are tilted relative to each other by 76.0 (1)° (molecule 1) and 79.9 (1)° (molecule 2). The other bond parameters in (I) are similar to those observed in 4-methyl-N-(2-chlorophenyl)- benzenesulfonamide (Gowda et al., 2010a), 4-methyl-N-(3-chlorophenyl)benzenesulfonamide (Gowda et al., 2010b), 4-methyl-N-(3,5-dichlorophenyl)benzenesulfonamide (Gowda et al., 2009) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The N—H···O hydrogen bonds (Table 1) pack the molecules into infinite chains in the direction of a- axis (Fig. 2).

Related literature top

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009, 2010a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of toluene (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-methylbenzenesulfonylchloride was treated with 2,3-dichloroaniline 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-methyl-N-(2,3-dichlorophenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra. The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Structure description top

For our study of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009, 2010a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

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

N-(2,3-Dichlorophenyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₃H₁₁Cl₂NO₂S	F(000) = 1296
M_r = 316.19	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.035 (3) Å	θ = 5.6–19.2°
b = 12.386 (2) Å	µ = 5.64 mm⁻¹
c = 15.993 (3) Å	T = 299 K
β = 98.30 (1)°	Prism, colourless
V = 2751.1 (9) Å³	0.50 × 0.45 × 0.40 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.131
Radiation source: fine-focus sealed tube	θ_max = 67.0°, θ_min = 3.9°
Graphite monochromator	h = −16→16
ω/2θ scans	k = −14→0
9784 measured reflections	l = −19→19
4903 independent reflections	3 standard reflections every 120 min
4359 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0914P)² + 0.5192P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
4903 reflections	Δρ_max = 0.81 e Å⁻³
352 parameters	Δρ_min = −0.56 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: 0.0038 (4)

Crystal data top

C₁₃H₁₁Cl₂NO₂S	V = 2751.1 (9) Å³
M_r = 316.19	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 14.035 (3) Å	µ = 5.64 mm⁻¹
b = 12.386 (2) Å	T = 299 K
c = 15.993 (3) Å	0.50 × 0.45 × 0.40 mm
β = 98.30 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.131
9784 measured reflections	3 standard reflections every 120 min
4903 independent reflections	intensity decay: 1.0%
4359 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.065	2 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.81 e Å⁻³
4903 reflections	Δρ_min = −0.56 e Å⁻³
352 parameters

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
C1	0.88559 (18)	0.0982 (2)	0.42938 (14)	0.0312 (6)
C2	0.9254 (2)	0.0053 (2)	0.40037 (17)	0.0404 (6)
H2	0.8955	−0.0612	0.4038	0.048*
C3	1.0094 (2)	0.0132 (3)	0.36653 (18)	0.0473 (7)
H3	1.0361	−0.0489	0.3468	0.057*
C4	1.05552 (19)	0.1107 (3)	0.36089 (16)	0.0412 (7)
C5	1.0132 (2)	0.2032 (3)	0.38929 (19)	0.0453 (7)
H5	1.0423	0.2700	0.3849	0.054*
C6	0.9292 (2)	0.1972 (2)	0.42354 (18)	0.0413 (6)
H6	0.9020	0.2592	0.4427	0.050*
C7	0.66060 (17)	0.0946 (2)	0.32818 (17)	0.0353 (6)
C8	0.64433 (18)	0.1597 (2)	0.25643 (17)	0.0375 (6)
C9	0.6067 (2)	0.1151 (3)	0.17875 (18)	0.0428 (7)
C10	0.5881 (2)	0.0062 (3)	0.1720 (2)	0.0578 (9)
H10	0.5641	−0.0237	0.1199	0.069*
C11	0.6048 (3)	−0.0574 (3)	0.2417 (3)	0.0637 (10)
H11	0.5925	−0.1311	0.2365	0.076*
C12	0.6398 (2)	−0.0151 (3)	0.3207 (2)	0.0530 (8)
H12	0.6493	−0.0597	0.3680	0.064*
C13	1.1486 (2)	0.1179 (4)	0.3250 (2)	0.0625 (10)
H13A	1.1354	0.1367	0.2662	0.075*
H13B	1.1809	0.0495	0.3311	0.075*
H13C	1.1888	0.1723	0.3548	0.075*
N1	0.69333 (16)	0.1410 (2)	0.40784 (15)	0.0379 (5)
H1N	0.700 (3)	0.2081 (15)	0.410 (2)	0.045*
O1	0.75897 (16)	−0.02137 (18)	0.48773 (13)	0.0491 (5)
O2	0.78830 (16)	0.16207 (18)	0.54657 (12)	0.0470 (5)
Cl1	0.67147 (7)	0.29473 (6)	0.26491 (5)	0.0542 (3)
Cl2	0.58337 (8)	0.19562 (9)	0.09061 (5)	0.0690 (3)
S1	0.77998 (4)	0.08962 (6)	0.47581 (4)	0.0344 (2)
C14	0.62488 (18)	0.4300 (2)	0.57233 (14)	0.0302 (5)
C15	0.5861 (2)	0.3271 (2)	0.57427 (16)	0.0372 (6)
H15	0.6173	0.2680	0.5548	0.045*
C16	0.5007 (2)	0.3142 (2)	0.60547 (18)	0.0420 (6)
H16	0.4740	0.2455	0.6066	0.050*
C17	0.45287 (19)	0.4019 (3)	0.63566 (16)	0.0397 (6)
C18	0.4933 (2)	0.5035 (3)	0.63213 (18)	0.0437 (7)
H18	0.4619	0.5629	0.6510	0.052*
C19	0.5792 (2)	0.5186 (2)	0.60121 (17)	0.0383 (6)
H19	0.6059	0.5872	0.5998	0.046*
C20	0.83949 (17)	0.4415 (2)	0.68958 (16)	0.0322 (5)
C21	0.87507 (17)	0.3732 (2)	0.75535 (16)	0.0318 (5)
C22	0.89966 (18)	0.4133 (2)	0.83721 (17)	0.0375 (6)
C23	0.8875 (2)	0.5210 (3)	0.8543 (2)	0.0484 (7)
H23	0.9037	0.5475	0.9089	0.058*
C24	0.8515 (2)	0.5880 (3)	0.7900 (2)	0.0509 (7)
H24	0.8421	0.6605	0.8014	0.061*
C25	0.8284 (2)	0.5505 (2)	0.70714 (19)	0.0440 (7)
H25	0.8056	0.5982	0.6639	0.053*
C26	0.3602 (2)	0.3853 (3)	0.6705 (2)	0.0560 (9)
H26A	0.3739	0.3697	0.7298	0.067*
H26B	0.3257	0.3259	0.6418	0.067*
H26C	0.3218	0.4495	0.6620	0.067*
N2	0.81882 (17)	0.39956 (19)	0.60644 (14)	0.0370 (5)
H2N	0.826 (2)	0.3316 (16)	0.603 (2)	0.044*
O3	0.73700 (16)	0.37678 (18)	0.46284 (11)	0.0475 (5)
O4	0.75082 (16)	0.55963 (18)	0.52425 (13)	0.0480 (5)
Cl3	0.88652 (6)	0.23746 (6)	0.73614 (5)	0.0526 (3)
Cl4	0.94255 (7)	0.32756 (8)	0.91866 (5)	0.0600 (3)
S2	0.73465 (5)	0.44706 (5)	0.53342 (4)	0.0342 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0288 (12)	0.0371 (14)	0.0268 (11)	0.0076 (10)	0.0013 (10)	−0.0017 (10)
C2	0.0439 (15)	0.0369 (14)	0.0404 (13)	0.0106 (12)	0.0061 (12)	−0.0029 (11)
C3	0.0477 (16)	0.0519 (17)	0.0430 (14)	0.0209 (15)	0.0094 (13)	−0.0032 (13)
C4	0.0297 (13)	0.0630 (19)	0.0302 (12)	0.0149 (13)	0.0021 (10)	0.0059 (12)
C5	0.0375 (15)	0.0479 (16)	0.0507 (16)	0.0007 (13)	0.0070 (13)	0.0035 (13)
C6	0.0379 (14)	0.0394 (15)	0.0475 (14)	0.0070 (12)	0.0089 (12)	−0.0044 (12)
C7	0.0203 (11)	0.0388 (14)	0.0458 (14)	0.0026 (10)	0.0010 (10)	−0.0021 (11)
C8	0.0250 (11)	0.0403 (14)	0.0472 (14)	0.0050 (11)	0.0055 (11)	−0.0079 (12)
C9	0.0314 (13)	0.0523 (17)	0.0436 (14)	0.0073 (13)	0.0021 (11)	−0.0059 (13)
C10	0.0478 (17)	0.056 (2)	0.0638 (19)	0.0036 (16)	−0.0109 (16)	−0.0218 (17)
C11	0.060 (2)	0.0422 (17)	0.080 (2)	−0.0048 (16)	−0.0183 (19)	−0.0116 (17)
C12	0.0467 (17)	0.0407 (16)	0.067 (2)	−0.0051 (14)	−0.0069 (16)	0.0032 (15)
C13	0.0407 (17)	0.099 (3)	0.0501 (17)	0.0165 (18)	0.0151 (14)	0.0137 (19)
N1	0.0304 (11)	0.0368 (12)	0.0465 (12)	0.0050 (10)	0.0062 (10)	−0.0011 (10)
O1	0.0523 (12)	0.0440 (12)	0.0517 (11)	−0.0005 (10)	0.0096 (10)	0.0120 (9)
O2	0.0531 (12)	0.0547 (12)	0.0342 (9)	0.0095 (10)	0.0102 (9)	−0.0046 (9)
Cl1	0.0739 (6)	0.0381 (4)	0.0496 (4)	0.0011 (3)	0.0049 (4)	0.0001 (3)
Cl2	0.0888 (7)	0.0725 (6)	0.0424 (4)	0.0130 (5)	−0.0019 (4)	0.0002 (4)
S1	0.0341 (4)	0.0386 (4)	0.0314 (3)	0.0055 (3)	0.0076 (3)	0.0024 (2)
C14	0.0315 (12)	0.0331 (12)	0.0247 (10)	0.0062 (10)	−0.0002 (10)	0.0018 (9)
C15	0.0435 (14)	0.0300 (12)	0.0386 (12)	0.0062 (12)	0.0076 (12)	−0.0001 (11)
C16	0.0411 (15)	0.0397 (15)	0.0445 (14)	−0.0033 (13)	0.0034 (12)	0.0034 (12)
C17	0.0295 (13)	0.0564 (17)	0.0308 (12)	0.0052 (12)	−0.0035 (10)	0.0041 (12)
C18	0.0374 (14)	0.0464 (16)	0.0472 (15)	0.0149 (13)	0.0062 (12)	−0.0023 (13)
C19	0.0418 (14)	0.0304 (13)	0.0410 (13)	0.0066 (12)	0.0005 (12)	−0.0027 (11)
C20	0.0214 (11)	0.0346 (13)	0.0403 (13)	−0.0015 (10)	0.0036 (10)	−0.0017 (11)
C21	0.0220 (11)	0.0311 (12)	0.0424 (13)	0.0003 (10)	0.0047 (10)	−0.0023 (11)
C22	0.0259 (11)	0.0449 (15)	0.0406 (13)	−0.0018 (11)	0.0007 (10)	0.0028 (12)
C23	0.0416 (15)	0.0538 (18)	0.0476 (15)	−0.0032 (14)	−0.0011 (13)	−0.0150 (14)
C24	0.0511 (17)	0.0367 (15)	0.0613 (18)	0.0000 (14)	−0.0044 (15)	−0.0127 (14)
C25	0.0441 (15)	0.0334 (14)	0.0509 (15)	0.0025 (12)	−0.0055 (13)	0.0003 (12)
C26	0.0375 (15)	0.083 (3)	0.0479 (16)	0.0029 (16)	0.0082 (13)	0.0082 (17)
N2	0.0370 (12)	0.0364 (12)	0.0379 (11)	0.0087 (10)	0.0061 (10)	−0.0006 (9)
O3	0.0581 (13)	0.0548 (12)	0.0315 (9)	0.0080 (11)	0.0128 (9)	−0.0008 (9)
O4	0.0569 (12)	0.0404 (11)	0.0480 (11)	−0.0015 (10)	0.0121 (10)	0.0119 (9)
Cl3	0.0709 (5)	0.0328 (4)	0.0515 (4)	0.0090 (3)	0.0001 (4)	0.0004 (3)
Cl4	0.0666 (5)	0.0630 (5)	0.0455 (4)	0.0009 (4)	−0.0081 (4)	0.0085 (4)
S2	0.0375 (4)	0.0354 (4)	0.0306 (3)	0.0034 (3)	0.0077 (3)	0.0043 (2)

Geometric parameters (Å, º) top

C1—C6	1.380 (4)	C14—C19	1.384 (4)
C1—C2	1.387 (4)	C14—C15	1.388 (4)
C1—S1	1.754 (2)	C14—S2	1.756 (2)
C2—C3	1.370 (4)	C15—C16	1.373 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.380 (5)	C16—C17	1.399 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.396 (4)	C17—C18	1.385 (4)
C4—C13	1.503 (4)	C17—C26	1.500 (4)
C5—C6	1.371 (4)	C18—C19	1.379 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.392 (4)	C20—C21	1.386 (4)
C7—C8	1.394 (4)	C20—C25	1.392 (4)
C7—N1	1.413 (4)	C20—N2	1.418 (3)
C8—C9	1.392 (4)	C21—C22	1.396 (4)
C8—Cl1	1.716 (3)	C21—Cl3	1.721 (3)
C9—C10	1.375 (5)	C22—C23	1.378 (4)
C9—Cl2	1.719 (3)	C22—Cl4	1.720 (3)
C10—C11	1.358 (6)	C23—C24	1.361 (5)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.390 (5)	C24—C25	1.397 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—H12	0.9300	C25—H25	0.9300
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600
N1—S1	1.638 (2)	N2—S2	1.645 (2)
N1—H1N	0.837 (18)	N2—H2N	0.851 (18)
O1—S1	1.425 (2)	O3—S2	1.430 (2)
O2—S1	1.436 (2)	O4—S2	1.424 (2)

C6—C1—C2	120.7 (2)	C19—C14—C15	121.2 (2)
C6—C1—S1	119.5 (2)	C19—C14—S2	119.7 (2)
C2—C1—S1	119.8 (2)	C15—C14—S2	119.1 (2)
C3—C2—C1	118.9 (3)	C16—C15—C14	118.8 (2)
C3—C2—H2	120.5	C16—C15—H15	120.6
C1—C2—H2	120.5	C14—C15—H15	120.6
C2—C3—C4	121.8 (3)	C15—C16—C17	121.5 (3)
C2—C3—H3	119.1	C15—C16—H16	119.3
C4—C3—H3	119.1	C17—C16—H16	119.3
C3—C4—C5	118.1 (3)	C18—C17—C16	118.1 (3)
C3—C4—C13	121.2 (3)	C18—C17—C26	121.5 (3)
C5—C4—C13	120.6 (3)	C16—C17—C26	120.4 (3)
C6—C5—C4	121.1 (3)	C19—C18—C17	121.5 (3)
C6—C5—H5	119.5	C19—C18—H18	119.3
C4—C5—H5	119.5	C17—C18—H18	119.3
C5—C6—C1	119.4 (3)	C18—C19—C14	118.9 (3)
C5—C6—H6	120.3	C18—C19—H19	120.6
C1—C6—H6	120.3	C14—C19—H19	120.6
C12—C7—C8	119.1 (3)	C21—C20—C25	118.5 (2)
C12—C7—N1	120.8 (3)	C21—C20—N2	119.3 (2)
C8—C7—N1	120.0 (3)	C25—C20—N2	122.1 (2)
C9—C8—C7	120.0 (3)	C20—C21—C22	120.5 (2)
C9—C8—Cl1	120.6 (2)	C20—C21—Cl3	119.61 (19)
C7—C8—Cl1	119.4 (2)	C22—C21—Cl3	119.9 (2)
C10—C9—C8	120.2 (3)	C23—C22—C21	120.6 (3)
C10—C9—Cl2	119.5 (2)	C23—C22—Cl4	119.1 (2)
C8—C9—Cl2	120.3 (2)	C21—C22—Cl4	120.2 (2)
C11—C10—C9	119.8 (3)	C24—C23—C22	118.9 (3)
C11—C10—H10	120.1	C24—C23—H23	120.5
C9—C10—H10	120.1	C22—C23—H23	120.5
C10—C11—C12	121.6 (3)	C23—C24—C25	121.7 (3)
C10—C11—H11	119.2	C23—C24—H24	119.2
C12—C11—H11	119.2	C25—C24—H24	119.2
C11—C12—C7	119.2 (3)	C20—C25—C24	119.7 (3)
C11—C12—H12	120.4	C20—C25—H25	120.1
C7—C12—H12	120.4	C24—C25—H25	120.1
C4—C13—H13A	109.5	C17—C26—H26A	109.5
C4—C13—H13B	109.5	C17—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C4—C13—H13C	109.5	C17—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C7—N1—S1	123.66 (19)	C20—N2—S2	124.27 (18)
C7—N1—H1N	117 (2)	C20—N2—H2N	114 (2)
S1—N1—H1N	107 (2)	S2—N2—H2N	113 (2)
O1—S1—O2	119.51 (13)	O4—S2—O3	119.53 (12)
O1—S1—N1	108.38 (13)	O4—S2—N2	108.34 (13)
O2—S1—N1	104.38 (12)	O3—S2—N2	104.28 (12)
O1—S1—C1	108.59 (13)	O4—S2—C14	108.40 (13)
O2—S1—C1	108.57 (12)	O3—S2—C14	109.14 (13)
N1—S1—C1	106.70 (12)	N2—S2—C14	106.39 (11)

C6—C1—C2—C3	0.7 (4)	C19—C14—C15—C16	0.1 (4)
S1—C1—C2—C3	−178.1 (2)	S2—C14—C15—C16	179.4 (2)
C1—C2—C3—C4	0.3 (4)	C14—C15—C16—C17	−0.5 (4)
C2—C3—C4—C5	−1.3 (4)	C15—C16—C17—C18	1.0 (4)
C2—C3—C4—C13	178.9 (3)	C15—C16—C17—C26	−179.2 (3)
C3—C4—C5—C6	1.4 (4)	C16—C17—C18—C19	−1.1 (4)
C13—C4—C5—C6	−178.8 (3)	C26—C17—C18—C19	179.1 (3)
C4—C5—C6—C1	−0.5 (4)	C17—C18—C19—C14	0.7 (4)
C2—C1—C6—C5	−0.5 (4)	C15—C14—C19—C18	−0.2 (4)
S1—C1—C6—C5	178.3 (2)	S2—C14—C19—C18	−179.5 (2)
C12—C7—C8—C9	0.8 (4)	C25—C20—C21—C22	−0.4 (4)
N1—C7—C8—C9	−176.2 (2)	N2—C20—C21—C22	177.4 (2)
C12—C7—C8—Cl1	−179.0 (2)	C25—C20—C21—Cl3	178.2 (2)
N1—C7—C8—Cl1	4.0 (3)	N2—C20—C21—Cl3	−4.0 (3)
C7—C8—C9—C10	−1.9 (4)	C20—C21—C22—C23	1.1 (4)
Cl1—C8—C9—C10	177.9 (2)	Cl3—C21—C22—C23	−177.6 (2)
C7—C8—C9—Cl2	178.22 (19)	C20—C21—C22—Cl4	179.30 (18)
Cl1—C8—C9—Cl2	−2.0 (3)	Cl3—C21—C22—Cl4	0.7 (3)
C8—C9—C10—C11	1.2 (5)	C21—C22—C23—C24	−0.3 (4)
Cl2—C9—C10—C11	−178.9 (3)	Cl4—C22—C23—C24	−178.5 (2)
C9—C10—C11—C12	0.5 (6)	C22—C23—C24—C25	−1.2 (5)
C10—C11—C12—C7	−1.7 (5)	C21—C20—C25—C24	−1.0 (4)
C8—C7—C12—C11	1.0 (4)	N2—C20—C25—C24	−178.8 (3)
N1—C7—C12—C11	177.9 (3)	C23—C24—C25—C20	1.9 (5)
C12—C7—N1—S1	47.9 (3)	C21—C20—N2—S2	150.1 (2)
C8—C7—N1—S1	−135.2 (2)	C25—C20—N2—S2	−32.2 (3)
C7—N1—S1—O1	−51.4 (2)	C20—N2—S2—O4	54.7 (2)
C7—N1—S1—O2	−179.8 (2)	C20—N2—S2—O3	−177.0 (2)
C7—N1—S1—C1	65.4 (2)	C20—N2—S2—C14	−61.7 (2)
C6—C1—S1—O1	−169.9 (2)	C19—C14—S2—O4	−10.5 (2)
C2—C1—S1—O1	8.9 (3)	C15—C14—S2—O4	170.1 (2)
C6—C1—S1—O2	−38.5 (3)	C19—C14—S2—O3	−142.2 (2)
C2—C1—S1—O2	140.3 (2)	C15—C14—S2—O3	38.4 (2)
C6—C1—S1—N1	73.5 (2)	C19—C14—S2—N2	105.8 (2)
C2—C1—S1—N1	−107.8 (2)	C15—C14—S2—N2	−73.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.84 (2)	2.29 (2)	3.086 (3)	160 (3)
N1—H1N···Cl1	0.84 (2)	2.54 (3)	2.957 (2)	112 (3)
N2—H2N···O2	0.85 (2)	2.32 (2)	3.104 (3)	154 (3)
N2—H2N···Cl3	0.85 (2)	2.46 (3)	2.944 (2)	117 (3)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁Cl₂NO₂S
M_r	316.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	14.035 (3), 12.386 (2), 15.993 (3)
β (°)	98.30 (1)
V (Å³)	2751.1 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	5.64
Crystal size (mm)	0.50 × 0.45 × 0.40

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9784, 4903, 4359
R_int	0.131
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.176, 1.11
No. of reflections	4903
No. of parameters	352
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)	0.81, −0.56

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···O3	0.837 (18)	2.29 (2)	3.086 (3)	160 (3)
N1—H1N···Cl1	0.837 (18)	2.54 (3)	2.957 (2)	112 (3)
N2—H2N···O2	0.851 (18)	2.32 (2)	3.104 (3)	154 (3)
N2—H2N···Cl3	0.851 (18)	2.46 (3)	2.944 (2)	117 (3)

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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