4-Chloro-2-methyl-N-(4-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810032320

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2329

https://doi.org/10.1107/S1600536810032320

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4-Chloro-2-methyl-N-(4-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 10 August 2010; accepted 11 August 2010; online 18 August 2010)

The asymmetric unit of the title compound, C₁₄H₁₄ClNO₂S, contains two independent molecules. The torsion angles of the C—SO₂—NH—C segments in the two molecules are −76.5 (5) and −48.3 (4)°. The two aromatic rings are tilted relative to each other by 76.6 (2)° in one molecule and 70.7 (2)° in the other. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

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. (2009 , 2010 ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 295.77
Monoclinic, P 2₁ /c
a = 10.544 (1) Å
b = 10.674 (1) Å
c = 25.196 (3) Å
β = 96.83 (1)°
V = 2815.6 (5) Å³
Z = 8
Cu Kα radiation
μ = 3.77 mm⁻¹
T = 299 K
0.30 × 0.30 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.398, T_max = 0.453
5050 measured reflections
4826 independent reflections
3917 reflections with I > 2σ(I)
R_int = 0.086
3 standard reflections every 120 min intensity decay: 2.4%

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.317
S = 1.43
4826 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 1.01 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4ⁱ	0.86	2.02	2.874 (5)	171
N2—H2A⋯O2ⁱ	0.86	2.23	2.968 (5)	144
Symmetry code: (i) -x+1, -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: https://doi.org/10.1107/S1600536810032320/bt5325sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032320/bt5325Isup2.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, 2010), in the present work, the structure of 4-chloro-2-methyl-N-(4-methylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit of (I) contains two independent molecules. In one of the molecules, the conformation of the N—C bond in the C—SO₂—NH—C segment has gauche torsions with respect to the S═O bonds. The conformation of the N—H bonds are syn to the ortho-methyl groups in the sulfonyl benzene rings of both the molecules, similar to that observed in 4-chloro-2-methyl-N-(phenyl)benzenesulfonamide (II) (Gowda et al., 2009) and 4-chloro-2-methyl-N-(4-chlorophenyl)benzenesulfonamide (III) (Gowda et al., 2010).

The torsion angles of the C—SO₂—NH—C segments in the two molecules of (I) are -76.5 (5)° and -48.3 (4)°, compared to the values of -61.9 (4)° and 69.7 (4)° in the two independent molecules of (II) and 55.0 (2)° in (III).

The sulfonyl and the aniline benzene rings in (I) are tilted relative to each other by 76.6 (2)° in molecule 1 and 70.7 (2)° in molecule 2, compared to the values of 86.6 (2)° and 83.0 (2)° in the two independent molecules of (II) and 67.0 (1)° in (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 into infinite zigzag row like chains. 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. (2009, 2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

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 4-methylaniline 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-(4-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).

The prism like colourless 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 into infinite zigzag row like chains. Part of the crystal structure is shown in Fig. 2.

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. (2009, 2010). 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. The molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing of the title compound with hydrogen bonding shown as dashed lines.

4-Chloro-2-methyl-N-(4-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₄ClNO₂S	F(000) = 1232
M_r = 295.77	D_x = 1.395 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.544 (1) Å	θ = 5.9–19.1°
b = 10.674 (1) Å	µ = 3.77 mm⁻¹
c = 25.196 (3) Å	T = 299 K
β = 96.83 (1)°	Prism, colourless
V = 2815.6 (5) Å³	0.30 × 0.30 × 0.25 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	3917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.086
Graphite monochromator	θ_max = 66.9°, θ_min = 3.5°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→1
T_min = 0.398, T_max = 0.453	l = 0→30
5050 measured reflections	3 standard reflections every 120 min
4826 independent reflections	intensity decay: 2.4%

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)] = 0.097	H-atom parameters constrained
wR(F²) = 0.317	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.43	(Δ/σ)_max = 0.019
4826 reflections	Δρ_max = 1.01 e Å⁻³
347 parameters	Δρ_min = −1.01 e Å⁻³
0 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: 0.0106 (15)

Crystal data top

C₁₄H₁₄ClNO₂S	V = 2815.6 (5) Å³
M_r = 295.77	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.544 (1) Å	µ = 3.77 mm⁻¹
b = 10.674 (1) Å	T = 299 K
c = 25.196 (3) Å	0.30 × 0.30 × 0.25 mm
β = 96.83 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3917 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.086
T_min = 0.398, T_max = 0.453	3 standard reflections every 120 min
5050 measured reflections	intensity decay: 2.4%
4826 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	0 restraints
wR(F²) = 0.317	H-atom parameters constrained
S = 1.43	Δρ_max = 1.01 e Å⁻³
4826 reflections	Δρ_min = −1.01 e Å⁻³
347 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	0.7092 (4)	0.2838 (5)	0.52199 (18)	0.0526 (11)
C2	0.6915 (4)	0.2131 (5)	0.4758 (2)	0.0597 (12)
H2	0.7045	0.1269	0.4776	0.072*
C3	0.6546 (5)	0.2695 (5)	0.42696 (19)	0.0607 (12)
H3	0.6429	0.2220	0.3958	0.073*
C4	0.6356 (5)	0.3958 (6)	0.4252 (2)	0.0659 (13)
C5	0.6518 (5)	0.4666 (5)	0.4711 (2)	0.0700 (14)
H5	0.6376	0.5525	0.4687	0.084*
C6	0.6879 (4)	0.4148 (5)	0.5198 (2)	0.0602 (12)
C7	1.0129 (4)	0.2164 (4)	0.58974 (17)	0.0538 (11)
C8	1.0262 (4)	0.1581 (7)	0.54233 (19)	0.0756 (17)
H8	0.9540	0.1354	0.5195	0.091*
C9	1.1459 (5)	0.1329 (6)	0.5282 (2)	0.0711 (15)
H9	1.1526	0.0907	0.4963	0.085*
C10	1.2545 (4)	0.1677 (5)	0.5594 (2)	0.0607 (12)
C11	1.2403 (5)	0.2234 (5)	0.6070 (3)	0.0746 (16)
H11	1.3130	0.2441	0.6299	0.090*
C12	1.1218 (5)	0.2505 (5)	0.6226 (2)	0.0621 (12)
H12	1.1156	0.2912	0.6548	0.075*
C13	0.7039 (5)	0.4992 (5)	0.5701 (2)	0.0690 (14)
H13A	0.7856	0.4836	0.5901	0.083*
H13B	0.6375	0.4808	0.5919	0.083*
H13C	0.6984	0.5856	0.5594	0.083*
C14	1.3851 (5)	0.1446 (7)	0.5412 (3)	0.0877 (18)
H14A	1.3786	0.1505	0.5029	0.105*
H14B	1.4145	0.0625	0.5522	0.105*
H14C	1.4444	0.2062	0.5568	0.105*
N1	0.8949 (4)	0.2489 (5)	0.60621 (16)	0.0686 (12)
H1A	0.8981	0.3005	0.6325	0.082*
O1	0.7566 (4)	0.0734 (3)	0.56948 (14)	0.0688 (10)
O2	0.6724 (3)	0.2426 (4)	0.62092 (13)	0.0732 (11)
Cl1	0.59229 (18)	0.46510 (19)	0.36388 (7)	0.0995 (7)
S1	0.75361 (10)	0.20254 (13)	0.58248 (4)	0.0579 (5)
C15	0.1219 (3)	0.6717 (4)	0.20092 (16)	0.0433 (9)
C16	0.0837 (4)	0.6148 (4)	0.15189 (19)	0.0539 (11)
H16	0.0822	0.5278	0.1496	0.065*
C17	0.0488 (5)	0.6840 (5)	0.10744 (19)	0.0623 (12)
H17	0.0223	0.6456	0.0749	0.075*
C18	0.0536 (4)	0.8125 (5)	0.1117 (2)	0.0627 (13)
C19	0.0895 (5)	0.8706 (4)	0.1592 (2)	0.0630 (13)
H19	0.0899	0.9576	0.1608	0.076*
C20	0.1252 (4)	0.8023 (4)	0.20515 (18)	0.0522 (10)
C21	0.4121 (4)	0.6191 (4)	0.24823 (16)	0.0447 (9)
C22	0.4261 (4)	0.5450 (4)	0.20440 (19)	0.0554 (11)
H22	0.3661	0.4835	0.1936	0.066*
C23	0.5307 (5)	0.5634 (4)	0.1766 (2)	0.0591 (12)
H23	0.5398	0.5125	0.1473	0.071*
C24	0.6215 (5)	0.6541 (4)	0.1908 (2)	0.0585 (11)
C25	0.6048 (5)	0.7257 (5)	0.2357 (3)	0.0754 (16)
H25	0.6653	0.7865	0.2470	0.090*
C26	0.5028 (4)	0.7098 (5)	0.2637 (2)	0.0630 (13)
H26	0.4943	0.7599	0.2933	0.076*
C27	0.1653 (5)	0.8727 (4)	0.2580 (2)	0.0624 (13)
H27A	0.2518	0.8514	0.2711	0.075*
H27B	0.1099	0.8492	0.2839	0.075*
H27C	0.1590	0.9614	0.2518	0.075*
C28	0.7328 (6)	0.6763 (6)	0.1611 (3)	0.0906 (19)
H28A	0.7071	0.7275	0.1304	0.109*
H28B	0.7644	0.5976	0.1498	0.109*
H28C	0.7989	0.7182	0.1839	0.109*
N2	0.3102 (3)	0.6066 (4)	0.27950 (14)	0.0513 (9)
H2A	0.3264	0.6176	0.3134	0.062*
O3	0.1584 (3)	0.4483 (3)	0.23600 (13)	0.0591 (9)
O4	0.0901 (3)	0.6035 (3)	0.29782 (12)	0.0591 (9)
Cl2	0.01664 (19)	0.9034 (2)	0.05495 (7)	0.1068 (7)
S2	0.16441 (9)	0.57267 (10)	0.25564 (4)	0.0463 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (2)	0.067 (3)	0.051 (2)	−0.0111 (19)	0.0023 (17)	−0.014 (2)
C2	0.050 (2)	0.065 (3)	0.063 (3)	−0.008 (2)	−0.001 (2)	−0.009 (2)
C3	0.056 (3)	0.078 (3)	0.046 (2)	−0.007 (2)	−0.0031 (19)	−0.009 (2)
C4	0.051 (2)	0.087 (4)	0.059 (3)	0.000 (2)	0.006 (2)	0.007 (3)
C5	0.061 (3)	0.061 (3)	0.088 (4)	0.005 (2)	0.007 (3)	0.002 (3)
C6	0.043 (2)	0.076 (3)	0.062 (3)	−0.003 (2)	0.0063 (19)	−0.016 (2)
C7	0.048 (2)	0.065 (3)	0.046 (2)	−0.0028 (19)	−0.0032 (18)	0.0065 (19)
C8	0.041 (2)	0.137 (5)	0.045 (2)	0.005 (3)	−0.0059 (19)	−0.014 (3)
C9	0.048 (2)	0.107 (4)	0.058 (3)	0.006 (3)	0.003 (2)	−0.009 (3)
C10	0.044 (2)	0.055 (3)	0.081 (3)	0.002 (2)	0.001 (2)	0.007 (2)
C11	0.051 (3)	0.068 (3)	0.099 (4)	−0.006 (2)	−0.017 (3)	−0.010 (3)
C12	0.059 (3)	0.058 (3)	0.065 (3)	−0.008 (2)	−0.009 (2)	−0.005 (2)
C13	0.060 (3)	0.069 (3)	0.080 (3)	0.001 (2)	0.017 (2)	−0.030 (3)
C14	0.047 (3)	0.092 (4)	0.124 (5)	0.004 (3)	0.010 (3)	−0.003 (4)
N1	0.047 (2)	0.110 (3)	0.048 (2)	−0.008 (2)	0.0038 (16)	−0.024 (2)
O1	0.076 (2)	0.073 (2)	0.058 (2)	−0.0125 (18)	0.0113 (17)	0.0022 (17)
O2	0.0535 (18)	0.124 (3)	0.0464 (18)	−0.0222 (19)	0.0228 (14)	−0.0159 (18)
Cl1	0.0931 (11)	0.1265 (15)	0.0774 (10)	0.0192 (10)	0.0034 (8)	0.0262 (9)
S1	0.0474 (7)	0.0810 (9)	0.0457 (7)	−0.0131 (5)	0.0077 (5)	−0.0067 (5)
C15	0.0366 (18)	0.048 (2)	0.046 (2)	0.0015 (16)	0.0062 (15)	−0.0090 (17)
C16	0.051 (2)	0.053 (2)	0.058 (3)	−0.0032 (19)	0.0037 (19)	−0.009 (2)
C17	0.062 (3)	0.076 (3)	0.048 (2)	0.009 (2)	0.004 (2)	−0.003 (2)
C18	0.050 (2)	0.083 (3)	0.056 (3)	0.020 (2)	0.010 (2)	0.008 (2)
C19	0.055 (3)	0.051 (3)	0.085 (4)	0.016 (2)	0.016 (2)	0.003 (2)
C20	0.049 (2)	0.048 (2)	0.060 (3)	0.0078 (18)	0.0066 (19)	−0.0085 (19)
C21	0.0405 (19)	0.048 (2)	0.045 (2)	0.0003 (17)	0.0023 (16)	0.0022 (17)
C22	0.056 (3)	0.048 (2)	0.063 (3)	−0.0056 (19)	0.013 (2)	−0.007 (2)
C23	0.066 (3)	0.051 (2)	0.064 (3)	0.004 (2)	0.020 (2)	−0.004 (2)
C24	0.056 (2)	0.053 (2)	0.070 (3)	0.002 (2)	0.023 (2)	0.004 (2)
C25	0.057 (3)	0.070 (3)	0.103 (4)	−0.019 (2)	0.026 (3)	−0.027 (3)
C26	0.052 (2)	0.071 (3)	0.067 (3)	−0.009 (2)	0.013 (2)	−0.023 (3)
C27	0.073 (3)	0.042 (2)	0.070 (3)	0.010 (2)	−0.001 (2)	−0.019 (2)
C28	0.086 (4)	0.082 (4)	0.114 (5)	−0.015 (3)	0.053 (4)	−0.006 (4)
N2	0.0413 (17)	0.070 (2)	0.0421 (18)	−0.0051 (16)	0.0027 (14)	0.0000 (16)
O3	0.065 (2)	0.0463 (17)	0.066 (2)	−0.0074 (14)	0.0089 (15)	0.0000 (14)
O4	0.0509 (17)	0.082 (2)	0.0487 (17)	−0.0144 (15)	0.0230 (13)	−0.0088 (15)
Cl2	0.1074 (13)	0.1270 (15)	0.0883 (12)	0.0445 (11)	0.0214 (10)	0.0449 (10)
S2	0.0427 (6)	0.0495 (6)	0.0469 (7)	−0.0047 (4)	0.0062 (4)	−0.0025 (4)

Geometric parameters (Å, º) top

C1—C2	1.381 (7)	C15—C16	1.392 (6)
C1—C6	1.416 (7)	C15—C20	1.399 (6)
C1—S1	1.768 (5)	C15—S2	1.753 (4)
C2—C3	1.384 (7)	C16—C17	1.356 (7)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.362 (8)	C17—C18	1.377 (8)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.374 (8)	C18—C19	1.360 (7)
C4—Cl1	1.726 (5)	C18—Cl2	1.734 (5)
C5—C6	1.360 (8)	C19—C20	1.381 (7)
C5—H5	0.9300	C19—H19	0.9300
C6—C13	1.547 (6)	C20—C27	1.543 (6)
C7—C8	1.369 (7)	C21—C22	1.381 (6)
C7—C12	1.382 (6)	C21—C26	1.384 (6)
C7—N1	1.401 (6)	C21—N2	1.412 (5)
C8—C9	1.378 (7)	C22—C23	1.389 (7)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.362 (7)	C23—C24	1.379 (7)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.363 (8)	C24—C25	1.394 (7)
C10—C14	1.522 (7)	C24—C28	1.484 (7)
C11—C12	1.384 (8)	C25—C26	1.365 (7)
C11—H11	0.9300	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13C	0.9600	C27—H27C	0.9600
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600
N1—S1	1.615 (4)	N2—S2	1.623 (3)
N1—H1A	0.8600	N2—H2A	0.8600
O1—S1	1.418 (4)	O3—S2	1.415 (3)
O2—S1	1.433 (3)	O4—S2	1.432 (3)

C2—C1—C6	120.2 (5)	C16—C15—C20	120.3 (4)
C2—C1—S1	116.9 (4)	C16—C15—S2	117.1 (3)
C6—C1—S1	122.9 (3)	C20—C15—S2	122.7 (3)
C1—C2—C3	120.5 (5)	C17—C16—C15	121.1 (4)
C1—C2—H2	119.8	C17—C16—H16	119.4
C3—C2—H2	119.8	C15—C16—H16	119.4
C4—C3—C2	118.9 (5)	C16—C17—C18	118.3 (5)
C4—C3—H3	120.5	C16—C17—H17	120.8
C2—C3—H3	120.5	C18—C17—H17	120.8
C3—C4—C5	120.9 (5)	C19—C18—C17	121.8 (5)
C3—C4—Cl1	118.4 (4)	C19—C18—Cl2	118.9 (4)
C5—C4—Cl1	120.7 (5)	C17—C18—Cl2	119.3 (4)
C6—C5—C4	121.9 (5)	C18—C19—C20	121.1 (5)
C6—C5—H5	119.0	C18—C19—H19	119.5
C4—C5—H5	119.0	C20—C19—H19	119.5
C5—C6—C1	117.6 (5)	C19—C20—C15	117.4 (4)
C5—C6—C13	119.6 (5)	C19—C20—C27	119.0 (4)
C1—C6—C13	122.8 (5)	C15—C20—C27	123.6 (4)
C8—C7—C12	118.6 (5)	C22—C21—C26	119.4 (4)
C8—C7—N1	123.9 (4)	C22—C21—N2	123.6 (4)
C12—C7—N1	117.5 (4)	C26—C21—N2	117.1 (4)
C7—C8—C9	120.5 (4)	C21—C22—C23	119.3 (4)
C7—C8—H8	119.8	C21—C22—H22	120.3
C9—C8—H8	119.8	C23—C22—H22	120.3
C10—C9—C8	122.0 (5)	C24—C23—C22	122.4 (4)
C10—C9—H9	119.0	C24—C23—H23	118.8
C8—C9—H9	119.0	C22—C23—H23	118.8
C9—C10—C11	117.0 (5)	C23—C24—C25	116.4 (4)
C9—C10—C14	120.7 (5)	C23—C24—C28	123.2 (5)
C11—C10—C14	122.3 (5)	C25—C24—C28	120.4 (5)
C10—C11—C12	122.6 (5)	C26—C25—C24	122.3 (5)
C10—C11—H11	118.7	C26—C25—H25	118.8
C12—C11—H11	118.7	C24—C25—H25	118.8
C11—C12—C7	119.2 (5)	C25—C26—C21	120.1 (5)
C11—C12—H12	120.4	C25—C26—H26	119.9
C7—C12—H12	120.4	C21—C26—H26	119.9
C6—C13—H13A	109.5	C20—C27—H27A	109.5
C6—C13—H13B	109.5	C20—C27—H27B	109.5
H13A—C13—H13B	109.5	H27A—C27—H27B	109.5
C6—C13—H13C	109.5	C20—C27—H27C	109.5
H13A—C13—H13C	109.5	H27A—C27—H27C	109.5
H13B—C13—H13C	109.5	H27B—C27—H27C	109.5
C10—C14—H14A	109.5	C24—C28—H28A	109.5
C10—C14—H14B	109.5	C24—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C10—C14—H14C	109.5	C24—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5
C7—N1—S1	128.8 (3)	C21—N2—S2	124.3 (3)
C7—N1—H1A	115.6	C21—N2—H2A	117.8
S1—N1—H1A	115.6	S2—N2—H2A	117.8
O1—S1—O2	118.6 (2)	O3—S2—O4	118.0 (2)
O1—S1—N1	109.8 (2)	O3—S2—N2	109.8 (2)
O2—S1—N1	104.9 (2)	O4—S2—N2	104.56 (19)
O1—S1—C1	106.8 (2)	O3—S2—C15	107.08 (19)
O2—S1—C1	108.5 (2)	O4—S2—C15	109.5 (2)
N1—S1—C1	107.9 (2)	N2—S2—C15	107.42 (19)

C6—C1—C2—C3	0.9 (7)	C20—C15—C16—C17	−0.2 (7)
S1—C1—C2—C3	178.9 (4)	S2—C15—C16—C17	179.8 (4)
C1—C2—C3—C4	−0.2 (7)	C15—C16—C17—C18	0.9 (7)
C2—C3—C4—C5	−0.5 (8)	C16—C17—C18—C19	−1.4 (8)
C2—C3—C4—Cl1	178.9 (4)	C16—C17—C18—Cl2	177.0 (4)
C3—C4—C5—C6	0.5 (8)	C17—C18—C19—C20	1.3 (8)
Cl1—C4—C5—C6	−178.9 (4)	Cl2—C18—C19—C20	−177.2 (4)
C4—C5—C6—C1	0.2 (8)	C18—C19—C20—C15	−0.5 (7)
C4—C5—C6—C13	−179.7 (5)	C18—C19—C20—C27	179.9 (4)
C2—C1—C6—C5	−0.9 (7)	C16—C15—C20—C19	0.0 (6)
S1—C1—C6—C5	−178.8 (4)	S2—C15—C20—C19	180.0 (3)
C2—C1—C6—C13	179.0 (4)	C16—C15—C20—C27	179.6 (4)
S1—C1—C6—C13	1.1 (6)	S2—C15—C20—C27	−0.5 (6)
C12—C7—C8—C9	0.8 (9)	C26—C21—C22—C23	−0.3 (7)
N1—C7—C8—C9	177.9 (6)	N2—C21—C22—C23	−179.1 (4)
C7—C8—C9—C10	−2.1 (10)	C21—C22—C23—C24	−0.6 (7)
C8—C9—C10—C11	3.3 (9)	C22—C23—C24—C25	1.4 (8)
C8—C9—C10—C14	−176.7 (6)	C22—C23—C24—C28	−179.1 (5)
C9—C10—C11—C12	−3.4 (8)	C23—C24—C25—C26	−1.5 (9)
C14—C10—C11—C12	176.6 (5)	C28—C24—C25—C26	179.0 (6)
C10—C11—C12—C7	2.2 (9)	C24—C25—C26—C21	0.7 (9)
C8—C7—C12—C11	−0.8 (8)	C22—C21—C26—C25	0.3 (8)
N1—C7—C12—C11	−178.1 (5)	N2—C21—C26—C25	179.1 (5)
C8—C7—N1—S1	14.5 (8)	C22—C21—N2—S2	−37.0 (6)
C12—C7—N1—S1	−168.4 (4)	C26—C21—N2—S2	144.2 (4)
C7—N1—S1—O1	39.5 (5)	C21—N2—S2—O3	67.9 (4)
C7—N1—S1—O2	167.9 (5)	C21—N2—S2—O4	−164.5 (4)
C7—N1—S1—C1	−76.5 (5)	C21—N2—S2—C15	−48.3 (4)
C2—C1—S1—O1	−2.3 (4)	C16—C15—S2—O3	4.1 (4)
C6—C1—S1—O1	175.6 (4)	C20—C15—S2—O3	−175.9 (3)
C2—C1—S1—O2	−131.2 (4)	C16—C15—S2—O4	−125.0 (3)
C6—C1—S1—O2	46.7 (4)	C20—C15—S2—O4	55.0 (4)
C2—C1—S1—N1	115.6 (4)	C16—C15—S2—N2	122.0 (3)
C6—C1—S1—N1	−66.5 (4)	C20—C15—S2—N2	−58.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4ⁱ	0.86	2.02	2.874 (5)	171
N2—H2A···O2ⁱ	0.86	2.23	2.968 (5)	144

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO₂S
M_r	295.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	10.544 (1), 10.674 (1), 25.196 (3)
β (°)	96.83 (1)
V (Å³)	2815.6 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	3.77
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.398, 0.453
No. of measured, independent and observed [I > 2σ(I)] reflections	5050, 4826, 3917
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.317, 1.43
No. of reflections	4826
No. of parameters	347
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −1.01

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—H1A···O4ⁱ	0.86	2.02	2.874 (5)	170.5
N2—H2A···O2ⁱ	0.86	2.23	2.968 (5)	144.4

Symmetry code: (i) −x+1, −y+1, −z+1.

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., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009). Acta Cryst. E65, o476. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o2000. Web of Science CSD 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
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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