4-Chloro-N-(2,3-dimethyl­phen­yl)-2-methyl­benzene­sulfonamide

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.; Shakuntala, K.

doi:10.1107/S1600536811037536

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2674

https://doi.org/10.1107/S1600536811037536

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4-Chloro-N-(2,3-dimethylphenyl)-2-methylbenzenesulfonamide

Vinola Z. Rodrigues,^a Sabine Foro,^b B. Thimme Gowda ^a ^* and K. Shakuntala ^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 8 September 2011; accepted 14 September 2011; online 17 September 2011)

The asymmetric unit of the title compound, C₁₅H₁₆ClNO₂S, contains two independent moleules. The conformation of the N—H bonds are anti to the ortho-methyl groups in the sulfonyl benzene rings of both the molecules, while the N—H bonds are anti to the ortho- and meta-methyl groups in the aniline ring of one of the molecules and syn in the other. Furthermore, the torsion angles of the C—SO₂—NH—C segments in the two molecules of are −66.8 (3) and 70.3 (3)°. The sulfonyl and the aniline benzene rings are oriented at angles of 44.1 (1) and 39.7 (1)° in the two molecules. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001 ). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004 ); Gowda et al. (2006 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ); Gowda et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₆ClNO₂S
M_r = 309.80
Triclinic, $[P \overline 1]$
a = 8.2747 (7) Å
b = 11.0464 (9) Å
c = 17.021 (1) Å
α = 82.722 (7)°
β = 79.529 (7)°
γ = 80.267 (7)°
V = 1500.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.40 × 0.28 × 0.14 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 = 0.858, T_max = 0.947
10437 measured reflections
6064 independent reflections
4140 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.166
S = 1.12
6064 reflections
373 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.85 (2)	2.15 (2)	2.971 (4)	162 (4)
N2—H2N⋯O2	0.85 (2)	2.12 (2)	2.954 (4)	166 (4)

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/S1600536811037536/bq2304sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037536/bq2304Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037536/bq2304Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Gowda et al., 2006), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2010), in the present work, the crystal structure of 4-Chloro-2-methyl-N- (2,3-dimethylphenyl)benzenesulfonamide (I) has been determined (Fig. 1).

The asymmetric unit of (I) contains two independent moleules. The conformation of the N—H bonds are anti to the ortho-methyl groups in the sulfonyl benzene rings of both the molecules, while, the N—H bonds are anti to the ortho- and meta-methyl groups in the anilino benzene ring of one of the molecules and syn in the other.

The torsion angles of the C—SO₂—NH—C segments in the two molecules of (I) are -66.8 (3)° and 70.3 (3)°, compared to the values of -61.9 (4)° and 69.7 (4)° in the two independent molecules of 4-chloro-2-methyl- N-(phenyl)-benzenesulfonamide (II) and -76.5 (5)° and -48.3 (4)° in 4-chloro-2-methyl-N-(4-methylphenyl)-benzenesulfonamide (III) (Gowda et al., 2010).

The sulfonyl and the aniline benzene rings in (I) are tilted relative to each other by 44.1 (1)° in molecule 1 and 39.7 (1)° in molecule 2, compared to the values of 86.6 (2)° and 83.0 (2)° in the two independent molecules of (II), and 76.6 (2)° in molecule 1 and 70.7 (2)° in molecule 2 of (III).

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

In the crystal, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules as dimers (Fig. 2).

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (2006), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2010).

Experimental top

The solution of m-chlorotoluene (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-methyl-4-chlorobenzenesulfonylchloride was treated with 2,3-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 cc). The resultant solid 4-chloro-2-methyl-N- (2,3-dimethylphenyl)-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 light pink single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Structure description top

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

In the crystal, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules as dimers (Fig. 2).

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (2006), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Gowda et al. (2010).

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 the title compound, 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-(2,3-dimethylphenyl)-2-methylbenzenesulfonamide top

Crystal data top

C₁₅H₁₆ClNO₂S	Z = 4
M_r = 309.80	F(000) = 648
Triclinic, P1	D_x = 1.371 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2747 (7) Å	Cell parameters from 3482 reflections
b = 11.0464 (9) Å	θ = 2.5–27.9°
c = 17.021 (1) Å	µ = 0.39 mm⁻¹
α = 82.722 (7)°	T = 293 K
β = 79.529 (7)°	Prism, light pink
γ = 80.267 (7)°	0.40 × 0.28 × 0.14 mm
V = 1500.5 (2) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	6064 independent reflections
Radiation source: fine-focus sealed tube	4140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→10
T_min = 0.858, T_max = 0.947	k = −13→13
10437 measured reflections	l = −20→21

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0505P)² + 1.8811P] where P = (F_o² + 2F_c²)/3
6064 reflections	(Δ/σ)_max = 0.001
373 parameters	Δρ_max = 0.58 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₅H₁₆ClNO₂S	γ = 80.267 (7)°
M_r = 309.80	V = 1500.5 (2) Å³
Triclinic, P1	Z = 4
a = 8.2747 (7) Å	Mo Kα radiation
b = 11.0464 (9) Å	µ = 0.39 mm⁻¹
c = 17.021 (1) Å	T = 293 K
α = 82.722 (7)°	0.40 × 0.28 × 0.14 mm
β = 79.529 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	6064 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	4140 reflections with I > 2σ(I)
T_min = 0.858, T_max = 0.947	R_int = 0.016
10437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	2 restraints
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.58 e Å⁻³
6064 reflections	Δρ_min = −0.36 e Å⁻³
373 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
Cl1	0.52306 (16)	1.04270 (13)	0.11188 (11)	0.1031 (5)
S1	0.01951 (12)	0.67472 (8)	0.25114 (5)	0.0460 (2)
O1	−0.1489 (3)	0.7348 (2)	0.26297 (15)	0.0552 (7)
O2	0.0856 (4)	0.6027 (2)	0.31763 (14)	0.0610 (7)
N1	0.0393 (4)	0.5780 (3)	0.18362 (17)	0.0443 (7)
H1N	0.134 (3)	0.533 (3)	0.182 (2)	0.053*
C1	0.1528 (4)	0.7859 (3)	0.2117 (2)	0.0437 (8)
C2	0.1054 (4)	0.8924 (3)	0.1619 (2)	0.0494 (9)
C3	0.2245 (5)	0.9684 (3)	0.1318 (3)	0.0590 (10)
H3	0.1971	1.0392	0.0982	0.071*
C4	0.3823 (5)	0.9412 (4)	0.1508 (3)	0.0597 (10)
C5	0.4282 (5)	0.8370 (4)	0.2000 (3)	0.0608 (11)
H5	0.5349	0.8195	0.2127	0.073*
C6	0.3138 (5)	0.7598 (4)	0.2299 (2)	0.0519 (9)
H6	0.3436	0.6888	0.2629	0.062*
C7	−0.0170 (4)	0.6186 (3)	0.10819 (19)	0.0388 (7)
C8	0.0950 (4)	0.6401 (3)	0.0383 (2)	0.0422 (8)
C9	0.0315 (5)	0.6788 (3)	−0.0338 (2)	0.0495 (9)
C10	−0.1381 (5)	0.6941 (4)	−0.0326 (3)	0.0591 (10)
H10	−0.1795	0.7191	−0.0803	0.071*
C11	−0.2468 (5)	0.6733 (4)	0.0370 (3)	0.0597 (11)
H11	−0.3607	0.6858	0.0366	0.072*
C12	−0.1861 (4)	0.6338 (3)	0.1073 (2)	0.0501 (9)
H12	−0.2589	0.6172	0.1545	0.060*
C13	−0.0679 (5)	0.9320 (4)	0.1388 (3)	0.0660 (12)
H13A	−0.1452	0.9589	0.1848	0.079*
H13B	−0.1029	0.8634	0.1206	0.079*
H13C	−0.0641	0.9986	0.0967	0.079*
C14	0.2798 (4)	0.6235 (4)	0.0383 (2)	0.0569 (10)
H14A	0.3052	0.5743	0.0864	0.068*
H14B	0.3141	0.7028	0.0362	0.068*
H14C	0.3376	0.5830	−0.0076	0.068*
C15	0.1476 (6)	0.7027 (4)	−0.1115 (2)	0.0740 (13)
H15A	0.2166	0.6269	−0.1253	0.089*
H15B	0.2163	0.7615	−0.1052	0.089*
H15C	0.0839	0.7348	−0.1534	0.089*
Cl2	−0.09225 (15)	−0.06815 (12)	0.40474 (9)	0.0840 (4)
S2	0.39623 (11)	0.31016 (8)	0.26485 (5)	0.0461 (2)
O3	0.3263 (3)	0.3796 (2)	0.19847 (15)	0.0607 (7)
O4	0.5651 (3)	0.2535 (2)	0.25283 (15)	0.0579 (7)
N2	0.3740 (4)	0.4077 (3)	0.33141 (18)	0.0475 (7)
H2N	0.282 (3)	0.456 (3)	0.334 (2)	0.057*
C16	0.2681 (4)	0.1958 (3)	0.3046 (2)	0.0424 (8)
C17	0.3215 (5)	0.0878 (3)	0.3519 (2)	0.0489 (9)
C18	0.2057 (5)	0.0090 (3)	0.3816 (2)	0.0558 (10)
H18	0.2368	−0.0631	0.4133	0.067*
C19	0.0459 (5)	0.0349 (3)	0.3652 (2)	0.0518 (9)
C20	−0.0065 (5)	0.1399 (4)	0.3189 (2)	0.0556 (10)
H20	−0.1145	0.1562	0.3077	0.067*
C21	0.1047 (4)	0.2201 (4)	0.2893 (2)	0.0511 (9)
H21	0.0706	0.2924	0.2585	0.061*
C22	0.4406 (4)	0.3718 (3)	0.4052 (2)	0.0404 (7)
C23	0.6040 (4)	0.3884 (3)	0.4066 (2)	0.0408 (8)
C24	0.6675 (5)	0.3519 (3)	0.4783 (2)	0.0510 (9)
C25	0.5644 (6)	0.3059 (4)	0.5452 (2)	0.0649 (12)
H25	0.6061	0.2827	0.5929	0.078*
C26	0.4023 (6)	0.2936 (4)	0.5431 (2)	0.0649 (12)
H26	0.3358	0.2638	0.5891	0.078*
C27	0.3396 (5)	0.3256 (3)	0.4727 (2)	0.0524 (9)
H27	0.2309	0.3164	0.4703	0.063*
C28	0.4975 (5)	0.0499 (4)	0.3714 (3)	0.0690 (12)
H28A	0.5307	0.1174	0.3918	0.083*
H28B	0.5729	0.0287	0.3235	0.083*
H28C	0.4994	−0.0201	0.4111	0.083*
C29	0.7049 (5)	0.4485 (4)	0.3345 (2)	0.0571 (10)
H29A	0.6317	0.5008	0.3023	0.069*
H29B	0.7720	0.3861	0.3033	0.069*
H29C	0.7754	0.4971	0.3517	0.069*
C30	0.8441 (5)	0.3647 (5)	0.4836 (3)	0.0803 (15)
H30A	0.8636	0.4473	0.4642	0.096*
H30B	0.9199	0.3073	0.4515	0.096*
H30C	0.8610	0.3476	0.5385	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0637 (8)	0.0905 (9)	0.1610 (15)	−0.0338 (7)	−0.0213 (8)	−0.0007 (9)
S1	0.0517 (6)	0.0501 (5)	0.0345 (4)	−0.0050 (4)	−0.0070 (4)	−0.0013 (4)
O1	0.0483 (15)	0.0622 (16)	0.0507 (15)	−0.0037 (12)	0.0005 (12)	−0.0073 (12)
O2	0.0770 (19)	0.0663 (17)	0.0369 (13)	−0.0031 (14)	−0.0143 (13)	0.0025 (12)
N1	0.0492 (18)	0.0428 (17)	0.0386 (15)	−0.0028 (13)	−0.0090 (14)	0.0018 (13)
C1	0.0432 (19)	0.0454 (19)	0.0437 (19)	−0.0010 (15)	−0.0113 (16)	−0.0107 (15)
C2	0.044 (2)	0.0425 (19)	0.064 (2)	−0.0018 (16)	−0.0161 (18)	−0.0065 (17)
C3	0.053 (2)	0.044 (2)	0.082 (3)	−0.0069 (18)	−0.020 (2)	−0.001 (2)
C4	0.044 (2)	0.060 (2)	0.079 (3)	−0.0130 (18)	−0.011 (2)	−0.016 (2)
C5	0.044 (2)	0.070 (3)	0.074 (3)	0.000 (2)	−0.022 (2)	−0.023 (2)
C6	0.050 (2)	0.057 (2)	0.052 (2)	−0.0012 (18)	−0.0198 (18)	−0.0066 (18)
C7	0.0441 (19)	0.0356 (17)	0.0376 (17)	−0.0076 (14)	−0.0076 (15)	−0.0030 (14)
C8	0.0436 (19)	0.0409 (18)	0.0429 (19)	−0.0085 (15)	−0.0064 (15)	−0.0050 (15)
C9	0.067 (3)	0.046 (2)	0.0381 (19)	−0.0141 (18)	−0.0113 (17)	−0.0037 (15)
C10	0.070 (3)	0.057 (2)	0.057 (2)	−0.005 (2)	−0.031 (2)	−0.0062 (19)
C11	0.049 (2)	0.064 (3)	0.073 (3)	−0.0065 (19)	−0.025 (2)	−0.014 (2)
C12	0.045 (2)	0.054 (2)	0.053 (2)	−0.0141 (17)	−0.0053 (17)	−0.0083 (17)
C13	0.050 (2)	0.045 (2)	0.102 (3)	−0.0053 (18)	−0.030 (2)	0.017 (2)
C14	0.046 (2)	0.071 (3)	0.051 (2)	−0.0146 (19)	0.0008 (17)	−0.0053 (19)
C15	0.097 (4)	0.081 (3)	0.044 (2)	−0.026 (3)	−0.006 (2)	0.003 (2)
Cl2	0.0711 (8)	0.0751 (8)	0.1086 (10)	−0.0281 (6)	−0.0147 (7)	0.0035 (7)
S2	0.0475 (5)	0.0498 (5)	0.0412 (5)	−0.0046 (4)	−0.0127 (4)	−0.0012 (4)
O3	0.0714 (18)	0.0662 (17)	0.0443 (14)	−0.0072 (14)	−0.0201 (13)	0.0061 (13)
O4	0.0504 (16)	0.0676 (17)	0.0542 (16)	−0.0069 (13)	−0.0039 (12)	−0.0093 (13)
N2	0.0470 (18)	0.0454 (17)	0.0506 (17)	0.0005 (13)	−0.0177 (15)	−0.0029 (14)
C16	0.046 (2)	0.0422 (19)	0.0406 (18)	−0.0005 (15)	−0.0127 (15)	−0.0086 (15)
C17	0.049 (2)	0.045 (2)	0.054 (2)	0.0033 (16)	−0.0197 (18)	−0.0062 (17)
C18	0.060 (2)	0.044 (2)	0.064 (2)	−0.0040 (18)	−0.017 (2)	−0.0008 (18)
C19	0.051 (2)	0.051 (2)	0.056 (2)	−0.0090 (17)	−0.0104 (18)	−0.0110 (18)
C20	0.043 (2)	0.065 (3)	0.063 (2)	−0.0058 (18)	−0.0175 (19)	−0.007 (2)
C21	0.046 (2)	0.056 (2)	0.051 (2)	0.0028 (17)	−0.0205 (17)	−0.0029 (17)
C22	0.0439 (19)	0.0348 (17)	0.0418 (18)	−0.0046 (14)	−0.0056 (15)	−0.0050 (14)
C23	0.0441 (19)	0.0369 (17)	0.0418 (18)	−0.0088 (14)	−0.0051 (15)	−0.0044 (14)
C24	0.056 (2)	0.048 (2)	0.052 (2)	0.0047 (17)	−0.0185 (18)	−0.0169 (17)
C25	0.098 (4)	0.052 (2)	0.041 (2)	0.010 (2)	−0.022 (2)	−0.0056 (18)
C26	0.091 (3)	0.053 (2)	0.043 (2)	−0.012 (2)	0.008 (2)	0.0007 (18)
C27	0.055 (2)	0.049 (2)	0.052 (2)	−0.0155 (17)	0.0028 (18)	−0.0066 (17)
C28	0.052 (2)	0.055 (2)	0.098 (3)	0.0012 (19)	−0.032 (2)	0.015 (2)
C29	0.050 (2)	0.063 (2)	0.060 (2)	−0.0185 (19)	−0.0006 (19)	−0.0093 (19)
C30	0.061 (3)	0.098 (4)	0.090 (3)	0.011 (3)	−0.035 (3)	−0.036 (3)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (4)	Cl2—C19	1.738 (4)
S1—O1	1.429 (3)	S2—O4	1.421 (3)
S1—O2	1.436 (2)	S2—O3	1.438 (2)
S1—N1	1.635 (3)	S2—N2	1.626 (3)
S1—C1	1.777 (4)	S2—C16	1.776 (4)
N1—C7	1.438 (4)	N2—C22	1.445 (4)
N1—H1N	0.850 (18)	N2—H2N	0.848 (18)
C1—C6	1.396 (5)	C16—C21	1.398 (5)
C1—C2	1.403 (5)	C16—C17	1.405 (5)
C2—C3	1.387 (5)	C17—C18	1.388 (5)
C2—C13	1.533 (5)	C17—C28	1.530 (5)
C3—C4	1.377 (5)	C18—C19	1.376 (5)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.376 (6)	C19—C20	1.371 (5)
C5—C6	1.368 (5)	C20—C21	1.371 (5)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C12	1.384 (5)	C22—C27	1.388 (5)
C7—C8	1.390 (5)	C22—C23	1.400 (5)
C8—C9	1.410 (5)	C23—C24	1.403 (5)
C8—C14	1.509 (5)	C23—C29	1.500 (5)
C9—C10	1.382 (5)	C24—C25	1.389 (6)
C9—C15	1.509 (5)	C24—C30	1.512 (6)
C10—C11	1.372 (6)	C25—C26	1.378 (6)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.374 (5)	C26—C27	1.374 (6)
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—H27	0.9300
C13—H13A	0.9600	C28—H28A	0.9600
C13—H13B	0.9600	C28—H28B	0.9600
C13—H13C	0.9600	C28—H28C	0.9600
C14—H14A	0.9600	C29—H29A	0.9600
C14—H14B	0.9600	C29—H29B	0.9600
C14—H14C	0.9600	C29—H29C	0.9600
C15—H15A	0.9600	C30—H30A	0.9600
C15—H15B	0.9600	C30—H30B	0.9600
C15—H15C	0.9600	C30—H30C	0.9600

O1—S1—O2	119.33 (16)	O4—S2—O3	119.65 (17)
O1—S1—N1	108.10 (16)	O4—S2—N2	107.93 (16)
O2—S1—N1	104.79 (15)	O3—S2—N2	104.94 (16)
O1—S1—C1	109.28 (16)	O4—S2—C16	109.10 (16)
O2—S1—C1	107.43 (17)	O3—S2—C16	106.85 (16)
N1—S1—C1	107.27 (16)	N2—S2—C16	107.82 (16)
C7—N1—S1	120.3 (2)	C22—N2—S2	120.5 (2)
C7—N1—H1N	117 (3)	C22—N2—H2N	118 (3)
S1—N1—H1N	109 (3)	S2—N2—H2N	112 (3)
C6—C1—C2	120.4 (3)	C21—C16—C17	120.1 (3)
C6—C1—S1	116.4 (3)	C21—C16—S2	116.5 (3)
C2—C1—S1	123.2 (3)	C17—C16—S2	123.3 (3)
C3—C2—C1	117.3 (3)	C18—C17—C16	117.0 (3)
C3—C2—C13	117.5 (3)	C18—C17—C28	118.0 (3)
C1—C2—C13	125.2 (3)	C16—C17—C28	124.9 (3)
C4—C3—C2	121.4 (4)	C19—C18—C17	121.6 (4)
C4—C3—H3	119.3	C19—C18—H18	119.2
C2—C3—H3	119.3	C17—C18—H18	119.2
C5—C4—C3	121.2 (4)	C20—C19—C18	121.6 (4)
C5—C4—Cl1	120.4 (3)	C20—C19—Cl2	119.5 (3)
C3—C4—Cl1	118.4 (3)	C18—C19—Cl2	119.0 (3)
C6—C5—C4	118.7 (4)	C19—C20—C21	118.1 (3)
C6—C5—H5	120.7	C19—C20—H20	120.9
C4—C5—H5	120.7	C21—C20—H20	120.9
C5—C6—C1	121.1 (4)	C20—C21—C16	121.5 (3)
C5—C6—H6	119.5	C20—C21—H21	119.2
C1—C6—H6	119.5	C16—C21—H21	119.2
C12—C7—C8	121.2 (3)	C27—C22—C23	122.2 (3)
C12—C7—N1	117.8 (3)	C27—C22—N2	119.2 (3)
C8—C7—N1	121.1 (3)	C23—C22—N2	118.6 (3)
C7—C8—C9	118.2 (3)	C22—C23—C24	117.9 (3)
C7—C8—C14	121.7 (3)	C22—C23—C29	120.8 (3)
C9—C8—C14	120.1 (3)	C24—C23—C29	121.3 (3)
C10—C9—C8	119.3 (4)	C25—C24—C23	118.9 (4)
C10—C9—C15	120.3 (4)	C25—C24—C30	120.3 (4)
C8—C9—C15	120.4 (4)	C23—C24—C30	120.8 (4)
C11—C10—C9	121.7 (4)	C26—C25—C24	122.2 (4)
C11—C10—H10	119.2	C26—C25—H25	118.9
C9—C10—H10	119.2	C24—C25—H25	118.9
C10—C11—C12	119.4 (4)	C27—C26—C25	119.6 (4)
C10—C11—H11	120.3	C27—C26—H26	120.2
C12—C11—H11	120.3	C25—C26—H26	120.2
C11—C12—C7	120.2 (4)	C26—C27—C22	119.0 (4)
C11—C12—H12	119.9	C26—C27—H27	120.5
C7—C12—H12	119.9	C22—C27—H27	120.5
C2—C13—H13A	109.5	C17—C28—H28A	109.5
C2—C13—H13B	109.5	C17—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28B	109.5
C2—C13—H13C	109.5	C17—C28—H28C	109.5
H13A—C13—H13C	109.5	H28A—C28—H28C	109.5
H13B—C13—H13C	109.5	H28B—C28—H28C	109.5
C8—C14—H14A	109.5	C23—C29—H29A	109.5
C8—C14—H14B	109.5	C23—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C8—C14—H14C	109.5	C23—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C9—C15—H15A	109.5	C24—C30—H30A	109.5
C9—C15—H15B	109.5	C24—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C9—C15—H15C	109.5	C24—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5

O1—S1—N1—C7	50.9 (3)	O4—S2—N2—C22	−47.4 (3)
O2—S1—N1—C7	179.2 (3)	O3—S2—N2—C22	−176.0 (3)
C1—S1—N1—C7	−66.8 (3)	C16—S2—N2—C22	70.3 (3)
O1—S1—C1—C6	151.7 (3)	O4—S2—C16—C21	−154.0 (3)
O2—S1—C1—C6	20.8 (3)	O3—S2—C16—C21	−23.3 (3)
N1—S1—C1—C6	−91.4 (3)	N2—S2—C16—C21	89.0 (3)
O1—S1—C1—C2	−31.0 (3)	O4—S2—C16—C17	28.5 (3)
O2—S1—C1—C2	−161.8 (3)	O3—S2—C16—C17	159.2 (3)
N1—S1—C1—C2	86.0 (3)	N2—S2—C16—C17	−88.4 (3)
C6—C1—C2—C3	0.5 (5)	C21—C16—C17—C18	0.0 (5)
S1—C1—C2—C3	−176.7 (3)	S2—C16—C17—C18	177.4 (3)
C6—C1—C2—C13	−178.9 (4)	C21—C16—C17—C28	178.8 (4)
S1—C1—C2—C13	3.8 (5)	S2—C16—C17—C28	−3.8 (5)
C1—C2—C3—C4	−0.7 (6)	C16—C17—C18—C19	0.4 (6)
C13—C2—C3—C4	178.7 (4)	C28—C17—C18—C19	−178.5 (4)
C2—C3—C4—C5	0.3 (7)	C17—C18—C19—C20	−0.1 (6)
C2—C3—C4—Cl1	−178.9 (3)	C17—C18—C19—Cl2	−179.9 (3)
C3—C4—C5—C6	0.3 (6)	C18—C19—C20—C21	−0.6 (6)
Cl1—C4—C5—C6	179.6 (3)	Cl2—C19—C20—C21	179.2 (3)
C4—C5—C6—C1	−0.5 (6)	C19—C20—C21—C16	1.0 (6)
C2—C1—C6—C5	0.1 (6)	C17—C16—C21—C20	−0.7 (6)
S1—C1—C6—C5	177.5 (3)	S2—C16—C21—C20	−178.3 (3)
S1—N1—C7—C12	−76.7 (4)	S2—N2—C22—C27	−92.8 (4)
S1—N1—C7—C8	104.2 (3)	S2—N2—C22—C23	89.1 (4)
C12—C7—C8—C9	0.5 (5)	C27—C22—C23—C24	2.7 (5)
N1—C7—C8—C9	179.5 (3)	N2—C22—C23—C24	−179.3 (3)
C12—C7—C8—C14	−179.8 (3)	C27—C22—C23—C29	−174.8 (3)
N1—C7—C8—C14	−0.8 (5)	N2—C22—C23—C29	3.2 (5)
C7—C8—C9—C10	0.0 (5)	C22—C23—C24—C25	−2.6 (5)
C14—C8—C9—C10	−179.7 (3)	C29—C23—C24—C25	174.8 (3)
C7—C8—C9—C15	−179.6 (3)	C22—C23—C24—C30	178.7 (3)
C14—C8—C9—C15	0.7 (5)	C29—C23—C24—C30	−3.8 (5)
C8—C9—C10—C11	0.4 (6)	C23—C24—C25—C26	0.8 (6)
C15—C9—C10—C11	−179.9 (4)	C30—C24—C25—C26	179.5 (4)
C9—C10—C11—C12	−1.4 (6)	C24—C25—C26—C27	1.1 (6)
C10—C11—C12—C7	1.8 (6)	C25—C26—C27—C22	−1.1 (6)
C8—C7—C12—C11	−1.4 (5)	C23—C22—C27—C26	−0.8 (5)
N1—C7—C12—C11	179.5 (3)	N2—C22—C27—C26	−178.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.85 (2)	2.15 (2)	2.971 (4)	162 (4)
N2—H2N···O2	0.85 (2)	2.12 (2)	2.954 (4)	166 (4)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆ClNO₂S
M_r	309.80
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.2747 (7), 11.0464 (9), 17.021 (1)
α, β, γ (°)	82.722 (7), 79.529 (7), 80.267 (7)
V (Å³)	1500.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.40 × 0.28 × 0.14

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	0.858, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	10437, 6064, 4140
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.166, 1.12
No. of reflections	6064
No. of parameters	373
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)	0.58, −0.36

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···O3	0.850 (18)	2.15 (2)	2.971 (4)	162 (4)
N2—H2N···O2	0.848 (18)	2.12 (2)	2.954 (4)	166 (4)

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS fellowship.

References

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