2,4-Dichloro-N-(2-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810035166

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2542

doi:10.1107/S1600536810035166

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2,4-Dichloro-N-(2-methylphenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b 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 25 August 2010; accepted 31 August 2010; online 11 September 2010)

In the title compound, C₁₃H₁₁Cl₂NO₂S, the methyl-substituted aromatic ring is disordered over two positions [occupancy ratio 0.705 (5):0.295 (5)]. The dihedral angles between the two aromatic rings are 74.9 (1) and 71.0 (3)° in the two disorder components. The crystal structure features centrosymmetric dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008 , 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 /c
a = 8.106 (1) Å
b = 14.854 (2) Å
c = 11.772 (1) Å
β = 97.34 (1)°
V = 1405.8 (3) Å³
Z = 4
Cu Kα radiation
μ = 5.52 mm⁻¹
T = 299 K
0.35 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: multi-scan (North et al., 1968 ) T_min = 0.248, T_max = 0.339
5256 measured reflections
2501 independent reflections
2205 reflections with I > 2σ(I)
R_int = 0.033
3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.098
S = 1.04
2501 reflections
240 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (2)	2.13 (2)	2.936 (2)	159 (2)
Symmetry code: (i) -x, -y+1, -z.

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/S1600536810035166/bt5340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035166/bt5340Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2008; Gowda et al. 2010a,b), the structure of 2,4-dichloro-N-(2-methylphenyl)-benzenesulfonamide (I) has been determined (Fig. 1). The methylsubstituted anilino ring is disordered. The conformations of the N—C bonds in the C—SO₂—NH—C segment have gauche torsions with respect to the S═O bonds in one of the disordered components.

The molecule is twisted at the S atom with the C1—SO₂—NH—C7 torsion angles of -85.1 (3)° and -47.2 (5)° in the major and minor components, respectively, compared to the values of 55.1 (3)° (molecule 1) and -48.3 (3)° (molecule 2) in 2,4-dichloro-N-(phenyl)-benzenesulfonamide (II) (Gowda et al., 2010b), -60.2 (2)° in 2,4-dichloro-N- (3-methylphenyl)benzenesulfonamide (III)(Gowda et al., 2010a) and 72.0 (2)° in N-(2-methylphenyl)-benzenesulfonamide (IV) (Gowda et al., 2008).

The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 74.9 (1)° and 71.0 (3)° in the two components, compared to the values of 80.5 (2)° in molecule 1 and 64.9 (1)° in molecule 2 of (II), 68.6 (1)° in (III) and 61.5 (1)° in (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers into infinite chains running parallel to the c-axis. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008, 2010a,b); For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-dichlorobenzene (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 2,4-dichlorobenzenesulfonylchloride was treated with o-toluidine 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 solid 2,4-dichloro-N-(2-methylphenyl)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 (Savitha & Gowda, 2006).

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: 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 labelling scheme and displacement ellipsoids are drawn at the 50% probability level. Only the major occupied component is shown.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dichloro-N-(2-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₁Cl₂NO₂S	F(000) = 648
M_r = 316.19	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.106 (1) Å	θ = 4.6–16.5°
b = 14.854 (2) Å	µ = 5.52 mm⁻¹
c = 11.772 (1) Å	T = 299 K
β = 97.34 (1)°	Prism, colourless
V = 1405.8 (3) Å³	0.35 × 0.25 × 0.25 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2205 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 67.0°, θ_min = 4.8°
ω/2θ scans	h = 0→9
Absorption correction: multi-scan (North et al., 1968)	k = −17→17
T_min = 0.248, T_max = 0.339	l = −14→13
5256 measured reflections	3 standard reflections every 120 min
2501 independent reflections	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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0521P)² + 0.4627P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.005
2501 reflections	Δρ_max = 0.44 e Å⁻³
240 parameters	Δρ_min = −0.38 e Å⁻³
8 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: 0.0021 (3)

Crystal data top

C₁₃H₁₁Cl₂NO₂S	V = 1405.8 (3) Å³
M_r = 316.19	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.106 (1) Å	µ = 5.52 mm⁻¹
b = 14.854 (2) Å	T = 299 K
c = 11.772 (1) Å	0.35 × 0.25 × 0.25 mm
β = 97.34 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2205 reflections with I > 2σ(I)
Absorption correction: multi-scan (North et al., 1968)	R_int = 0.033
T_min = 0.248, T_max = 0.339	3 standard reflections every 120 min
5256 measured reflections	intensity decay: 1.0%
2501 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	8 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.44 e Å⁻³
2501 reflections	Δρ_min = −0.38 e Å⁻³
240 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	Occ. (<1)
C1	0.1368 (2)	0.33703 (12)	0.20574 (15)	0.0386 (4)
C2	0.2961 (3)	0.36013 (12)	0.18389 (16)	0.0404 (4)
C3	0.4340 (3)	0.31932 (15)	0.24250 (19)	0.0502 (5)
H3	0.5403	0.3342	0.2269	0.060*
C4	0.4113 (3)	0.25585 (15)	0.3250 (2)	0.0533 (5)
C5	0.2555 (3)	0.23232 (14)	0.34875 (19)	0.0520 (5)
H5	0.2430	0.1899	0.4051	0.062*
C6	0.1183 (3)	0.27211 (13)	0.28857 (17)	0.0450 (5)
H6	0.0124	0.2556	0.3032	0.054*
C7A	−0.1071 (5)	0.5236 (2)	0.2565 (3)	0.0446 (8)	0.705 (5)
C8A	0.0002 (5)	0.5685 (2)	0.3379 (4)	0.0532 (9)	0.705 (5)
C9A	−0.072 (2)	0.6089 (7)	0.4284 (7)	0.071 (3)	0.705 (5)
H9A	−0.0061	0.6448	0.4807	0.085*	0.705 (5)
C10A	−0.2337 (8)	0.5970 (3)	0.4412 (4)	0.0903 (16)	0.705 (5)
H10A	−0.2750	0.6187	0.5061	0.108*	0.705 (5)
C11A	−0.3369 (8)	0.5525 (4)	0.3577 (6)	0.0851 (17)	0.705 (5)
H11A	−0.4495	0.5469	0.3644	0.102*	0.705 (5)
C12A	−0.2749 (7)	0.5167 (3)	0.2651 (5)	0.0608 (12)	0.705 (5)
H12A	−0.3455	0.4877	0.2081	0.073*	0.705 (5)
C13A	0.1816 (13)	0.5795 (9)	0.3311 (9)	0.074 (3)	0.705 (5)
H13A	0.1967	0.6110	0.2619	0.088*	0.705 (5)
H13B	0.2331	0.5214	0.3309	0.088*	0.705 (5)
H13C	0.2316	0.6134	0.3960	0.088*	0.705 (5)
N1	−0.0460 (2)	0.49066 (12)	0.15829 (14)	0.0462 (4)
H1N	0.003 (3)	0.5230 (16)	0.1141 (19)	0.055*
O1	−0.1805 (2)	0.34262 (12)	0.17683 (16)	0.0629 (4)
O2	−0.0363 (2)	0.37672 (10)	0.01067 (12)	0.0560 (4)
Cl1	0.32844 (7)	0.44230 (4)	0.08450 (4)	0.05248 (18)
Cl2	0.58543 (10)	0.20713 (6)	0.40131 (8)	0.0887 (3)
S1	−0.04615 (6)	0.38428 (3)	0.13094 (4)	0.04322 (17)
C7B	−0.0109 (13)	0.5386 (5)	0.2733 (7)	0.043 (2)	0.295 (5)
C8B	−0.1310 (11)	0.5537 (5)	0.3435 (6)	0.055 (2)	0.295 (5)
C9B	−0.080 (4)	0.5925 (14)	0.4520 (14)	0.052 (4)	0.295 (5)
H9B	−0.1519	0.5919	0.5073	0.062*	0.295 (5)
C10B	0.0727 (13)	0.6305 (6)	0.4773 (8)	0.068 (3)	0.295 (5)
H10B	0.0964	0.6653	0.5429	0.082*	0.295 (5)
C11B	0.1903 (13)	0.6177 (7)	0.4071 (10)	0.074 (3)	0.295 (5)
H11B	0.2974	0.6398	0.4274	0.088*	0.295 (5)
C12B	0.151 (3)	0.5715 (16)	0.3043 (19)	0.054 (4)	0.295 (5)
H12B	0.2317	0.5624	0.2561	0.064*	0.295 (5)
C13B	−0.3078 (15)	0.5262 (10)	0.3116 (11)	0.067 (4)	0.295 (5)
H13D	−0.3132	0.4623	0.2989	0.081*	0.295 (5)
H13E	−0.3532	0.5569	0.2429	0.081*	0.295 (5)
H13F	−0.3709	0.5415	0.3725	0.081*	0.295 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0406 (10)	0.0357 (9)	0.0390 (9)	−0.0031 (8)	0.0029 (7)	−0.0023 (7)
C2	0.0429 (11)	0.0354 (9)	0.0432 (10)	−0.0030 (8)	0.0065 (8)	−0.0020 (8)
C3	0.0395 (11)	0.0490 (12)	0.0620 (13)	−0.0002 (9)	0.0059 (9)	−0.0007 (10)
C4	0.0516 (13)	0.0457 (11)	0.0600 (12)	0.0073 (10)	−0.0036 (10)	0.0029 (10)
C5	0.0623 (14)	0.0420 (10)	0.0511 (11)	−0.0001 (10)	0.0051 (10)	0.0077 (9)
C6	0.0460 (11)	0.0422 (10)	0.0474 (11)	−0.0066 (9)	0.0082 (8)	0.0013 (8)
C7A	0.050 (2)	0.0363 (16)	0.0468 (19)	0.0050 (15)	0.0028 (16)	0.0013 (13)
C8A	0.060 (3)	0.0448 (18)	0.053 (2)	0.0001 (16)	0.0025 (18)	0.0001 (16)
C9A	0.111 (5)	0.051 (5)	0.050 (4)	−0.003 (3)	0.012 (4)	−0.002 (4)
C10A	0.110 (4)	0.084 (3)	0.085 (3)	0.007 (3)	0.043 (3)	−0.020 (2)
C11A	0.071 (3)	0.084 (4)	0.109 (5)	0.005 (3)	0.047 (3)	−0.022 (3)
C12A	0.056 (3)	0.053 (2)	0.074 (4)	0.0074 (18)	0.013 (2)	−0.007 (2)
C13A	0.059 (4)	0.080 (5)	0.077 (7)	−0.011 (3)	−0.006 (4)	−0.019 (4)
N1	0.0526 (11)	0.0438 (9)	0.0424 (9)	0.0006 (8)	0.0069 (7)	0.0035 (7)
O1	0.0401 (9)	0.0595 (9)	0.0888 (12)	−0.0069 (7)	0.0073 (8)	0.0146 (8)
O2	0.0650 (11)	0.0557 (9)	0.0431 (8)	−0.0070 (7)	−0.0094 (7)	−0.0048 (6)
Cl1	0.0507 (3)	0.0533 (3)	0.0544 (3)	−0.0078 (2)	0.0107 (2)	0.0094 (2)
Cl2	0.0639 (4)	0.0861 (5)	0.1097 (6)	0.0179 (4)	−0.0134 (4)	0.0310 (4)
S1	0.0373 (3)	0.0435 (3)	0.0472 (3)	−0.00531 (19)	−0.00115 (19)	0.00201 (19)
C7B	0.062 (7)	0.032 (4)	0.033 (4)	0.002 (4)	−0.001 (4)	−0.008 (3)
C8B	0.068 (6)	0.045 (4)	0.054 (5)	0.007 (4)	0.017 (4)	−0.002 (3)
C9B	0.091 (10)	0.035 (7)	0.033 (6)	0.004 (6)	0.022 (6)	0.007 (5)
C10B	0.093 (7)	0.053 (5)	0.057 (5)	0.004 (5)	0.004 (5)	−0.020 (4)
C11B	0.064 (6)	0.075 (6)	0.076 (6)	−0.003 (5)	−0.014 (5)	−0.030 (5)
C12B	0.065 (11)	0.046 (6)	0.047 (7)	−0.006 (6)	−0.004 (7)	−0.014 (5)
C13B	0.048 (8)	0.088 (10)	0.069 (10)	−0.002 (6)	0.021 (6)	−0.021 (7)

Geometric parameters (Å, º) top

C1—C2	1.391 (3)	C12A—H12A	0.9300
C1—C6	1.393 (3)	C13A—H13A	0.9600
C1—S1	1.770 (2)	C13A—H13B	0.9600
C2—C3	1.377 (3)	C13A—H13C	0.9600
C2—Cl1	1.7337 (19)	N1—C7B	1.524 (9)
C3—C4	1.382 (3)	N1—S1	1.6125 (18)
C3—H3	0.9300	N1—H1N	0.844 (17)
C4—C5	1.373 (3)	O1—S1	1.4183 (17)
C4—Cl2	1.732 (2)	O2—S1	1.4326 (15)
C5—C6	1.373 (3)	C7B—C8B	1.374 (11)
C5—H5	0.9300	C7B—C12B	1.402 (17)
C6—H6	0.9300	C8B—C9B	1.415 (16)
C7A—C12A	1.381 (7)	C8B—C13B	1.492 (13)
C7A—C8A	1.381 (5)	C9B—C10B	1.36 (3)
C7A—N1	1.403 (4)	C9B—H9B	0.9300
C8A—C9A	1.413 (11)	C10B—C11B	1.352 (15)
C8A—C13A	1.492 (11)	C10B—H10B	0.9300
C9A—C10A	1.350 (15)	C11B—C12B	1.393 (16)
C9A—H9A	0.9300	C11B—H11B	0.9300
C10A—C11A	1.375 (8)	C12B—H12B	0.9300
C10A—H10A	0.9300	C13B—H13D	0.9600
C11A—C12A	1.366 (7)	C13B—H13E	0.9600
C11A—H11A	0.9300	C13B—H13F	0.9600

C2—C1—C6	119.02 (18)	C8A—C13A—H13C	109.5
C2—C1—S1	123.26 (14)	H13A—C13A—H13C	109.5
C6—C1—S1	117.69 (15)	H13B—C13A—H13C	109.5
C3—C2—C1	120.80 (19)	C7A—N1—C7B	31.8 (3)
C3—C2—Cl1	117.70 (16)	C7A—N1—S1	121.00 (19)
C1—C2—Cl1	121.49 (15)	C7B—N1—S1	129.1 (3)
C2—C3—C4	118.6 (2)	C7A—N1—H1N	123.6 (17)
C2—C3—H3	120.7	C7B—N1—H1N	103.4 (17)
C4—C3—H3	120.7	S1—N1—H1N	115.0 (17)
C5—C4—C3	121.7 (2)	O1—S1—O2	118.99 (10)
C5—C4—Cl2	119.84 (18)	O1—S1—N1	109.42 (11)
C3—C4—Cl2	118.43 (18)	O2—S1—N1	105.99 (9)
C4—C5—C6	119.4 (2)	O1—S1—C1	105.83 (10)
C4—C5—H5	120.3	O2—S1—C1	108.16 (10)
C6—C5—H5	120.3	N1—S1—C1	108.06 (9)
C5—C6—C1	120.5 (2)	C8B—C7B—C12B	119.8 (13)
C5—C6—H6	119.8	C8B—C7B—N1	123.0 (9)
C1—C6—H6	119.8	C12B—C7B—N1	117.1 (11)
C12A—C7A—C8A	121.6 (4)	C7B—C8B—C9B	117.4 (14)
C12A—C7A—N1	119.3 (4)	C7B—C8B—C13B	122.4 (9)
C8A—C7A—N1	118.9 (4)	C9B—C8B—C13B	120.1 (14)
C7A—C8A—C9A	116.3 (7)	C10B—C9B—C8B	121.5 (16)
C7A—C8A—C13A	123.6 (5)	C10B—C9B—H9B	119.2
C9A—C8A—C13A	120.0 (7)	C8B—C9B—H9B	119.2
C10A—C9A—C8A	122.0 (8)	C11B—C10B—C9B	120.1 (10)
C10A—C9A—H9A	119.0	C11B—C10B—H10B	120.0
C8A—C9A—H9A	119.0	C9B—C10B—H10B	120.0
C9A—C10A—C11A	119.6 (5)	C10B—C11B—C12B	119.9 (13)
C9A—C10A—H10A	120.2	C10B—C11B—H11B	120.1
C11A—C10A—H10A	120.2	C12B—C11B—H11B	120.1
C12A—C11A—C10A	120.4 (6)	C11B—C12B—C7B	120.1 (18)
C12A—C11A—H11A	119.8	C11B—C12B—H12B	120.0
C10A—C11A—H11A	119.8	C7B—C12B—H12B	120.0
C11A—C12A—C7A	119.7 (6)	C8B—C13B—H13D	109.5
C11A—C12A—H12A	120.1	C8B—C13B—H13E	109.5
C7A—C12A—H12A	120.1	H13D—C13B—H13E	109.5
C8A—C13A—H13A	109.5	C8B—C13B—H13F	109.5
C8A—C13A—H13B	109.5	H13D—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13E—C13B—H13F	109.5

C6—C1—C2—C3	0.4 (3)	C7A—N1—S1—O1	29.7 (3)
S1—C1—C2—C3	−178.13 (16)	C7B—N1—S1—O1	67.6 (5)
C6—C1—C2—Cl1	−178.41 (15)	C7A—N1—S1—O2	159.2 (2)
S1—C1—C2—Cl1	3.1 (2)	C7B—N1—S1—O2	−162.9 (5)
C1—C2—C3—C4	−1.0 (3)	C7A—N1—S1—C1	−85.1 (2)
Cl1—C2—C3—C4	177.79 (16)	C7B—N1—S1—C1	−47.2 (5)
C2—C3—C4—C5	0.5 (3)	C2—C1—S1—O1	179.13 (16)
C2—C3—C4—Cl2	−178.15 (17)	C6—C1—S1—O1	0.62 (18)
C3—C4—C5—C6	0.6 (3)	C2—C1—S1—O2	50.59 (18)
Cl2—C4—C5—C6	179.28 (17)	C6—C1—S1—O2	−127.93 (15)
C4—C5—C6—C1	−1.3 (3)	C2—C1—S1—N1	−63.73 (18)
C2—C1—C6—C5	0.8 (3)	C6—C1—S1—N1	117.75 (16)
S1—C1—C6—C5	179.39 (16)	C7A—N1—C7B—C8B	1.1 (5)
C12A—C7A—C8A—C9A	−1.7 (7)	S1—N1—C7B—C8B	−86.0 (8)
N1—C7A—C8A—C9A	173.1 (5)	C7A—N1—C7B—C12B	−176.0 (15)
C12A—C7A—C8A—C13A	−178.6 (8)	S1—N1—C7B—C12B	96.9 (13)
N1—C7A—C8A—C13A	−3.8 (8)	C12B—C7B—C8B—C9B	−7.9 (19)
C7A—C8A—C9A—C10A	6.4 (11)	N1—C7B—C8B—C9B	175.0 (12)
C13A—C8A—C9A—C10A	−176.6 (9)	C12B—C7B—C8B—C13B	175.7 (15)
C8A—C9A—C10A—C11A	−7.2 (13)	N1—C7B—C8B—C13B	−1.4 (12)
C9A—C10A—C11A—C12A	3.2 (11)	C7B—C8B—C9B—C10B	14 (3)
C10A—C11A—C12A—C7A	1.3 (9)	C13B—C8B—C9B—C10B	−170.0 (16)
C8A—C7A—C12A—C11A	−2.0 (7)	C8B—C9B—C10B—C11B	−12 (3)
N1—C7A—C12A—C11A	−176.8 (5)	C9B—C10B—C11B—C12B	5 (2)
C12A—C7A—N1—C7B	177.2 (8)	C10B—C11B—C12B—C7B	0 (3)
C8A—C7A—N1—C7B	2.3 (5)	C8B—C7B—C12B—C11B	1 (2)
C12A—C7A—N1—S1	−67.5 (4)	N1—C7B—C12B—C11B	178.6 (13)
C8A—C7A—N1—S1	117.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.13 (2)	2.936 (2)	159 (2)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁Cl₂NO₂S
M_r	316.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	8.106 (1), 14.854 (2), 11.772 (1)
β (°)	97.34 (1)
V (Å³)	1405.8 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	5.52
Crystal size (mm)	0.35 × 0.25 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan (North et al., 1968)
T_min, T_max	0.248, 0.339
No. of measured, independent and observed [I > 2σ(I)] reflections	5256, 2501, 2205
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.098, 1.04
No. of reflections	2501
No. of parameters	240
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.38

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···O2ⁱ	0.844 (17)	2.133 (18)	2.936 (2)	159 (2)

Symmetry code: (i) −x, −y+1, −z.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1692. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010a). Acta Cryst. E66, o1520. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010b). Private communication (refcode CCDC 740692). CCDC, Union Road, Cambridge, England. 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
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600–606. 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

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Volume 66| Part 10| October 2010| Page o2542

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