4-Chloro-2-methyl-N-phenyl­benzene­sulfonamide

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

doi:10.1107/S1600536809003845

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o476

doi:10.1107/S1600536809003845

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4-Chloro-2-methyl-N-phenylbenzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a K. S. Babitha ^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 17 January 2009; accepted 2 February 2009; online 6 February 2009)

There are two molecules in the asymmetric unit of the title compound, C₁₃H₁₂ClNO₂S, with similar conformations. The orientations of the ortho-methyl groups in the sulfonyl benzene rings are in the direction of the N—H bonds of the sulfonamide groups. In the crystal, the molecules are each linked into centrosymmetric dimers through N—H⋯O hydrogen bonds and packed into a layered structure diagonally in the bc plane.

Related literature

For related structures, see: Gelbrich et al. (2007 ); Gowda et al. (2008a ,b , 2009 ); Perlovich et al. (2006 )

Experimental

Crystal data

C₁₃H₁₂ClNO₂S
M_r = 281.75
Triclinic, $[P \overline 1]$
a = 8.609 (1) Å
b = 11.143 (1) Å
c = 14.726 (2) Å
α = 98.618 (7)°
β = 90.951 (8)°
γ = 105.79 (1)°
V = 1341.6 (3) Å³
Z = 4
Cu Kα radiation
μ = 3.93 mm⁻¹
T = 299 (2) K
0.33 × 0.23 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.350, T_max = 0.729
7620 measured reflections
4784 independent reflections
2980 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.176
S = 1.03
4784 reflections
333 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.91 (5)	2.02 (5)	2.922 (4)	175 (4)
N2—H2N⋯O3ⁱⁱ	0.88 (4)	2.03 (5)	2.906 (4)	173 (4)
Symmetry codes: (i) -x+1, -y+2, -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, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003845/fj2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003845/fj2192Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides, the structure of N-(phenyl)-2-methyl-4-chlorobenzenesulfonamide (NP2M4CBSA) has been determined (Gowda et al. 2008a,b, 2009). The asymmetric unit of NP2M4CBSA contains 2 molecules. The orientations of the ortho- methyl groups in the sulfonyl benzene rings are in the direction of the N—H bonds of the sulfonamido groups (Fig. 1). The opposite signs of the C—S—N—C torsion angles in the two independent molecules, -61.9 (4)° (molecule 1) and 69.7 (4)° (molecule 2), indicates that they have opposite chirality, although the choice of the chirality of the second molecule relative to the first may be arbitary. The two benzene rings in NP2M4CBSA are tilted relative to each other by 86.6 (2)° in the molecule 1 and 83.0 (2)° in molecule 2, compared with the values of 67.5 (1)° (molecule 1) and 72.9 (1)° (molecule 2) for N-(phenyl)-2,4-dimethylbenzenesulfonamide (NP24DMBSA) (Gowda et al., 2009). The other bond parameters in NP2M4CBSA are similar to those observed for N-(2-methylphenyl)-benzenesulfonamide (Gowda et al., 2008a), NP24DMBSA and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007; Gowda et al., 2008b). The crystal packing of molecules in NP2M4CBSA via intermolecular N—H···O hydrogen bonds (Table 1) is shown in Fig.2.

Related literature top

For related structures, see: Gelbrich et al. (2007); Gowda et al. (2008a,b, 2009); Perlovich et al. (2006)

Experimental top

The solution of m-chlorotoluene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 aniline 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 N-(phenyl)-2-methyl-4-chlorobenzenesulfonamide 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.

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, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

4-Chloro-2-methyl-N-phenylbenzenesulfonamide top

Crystal data top

C₁₃H₁₂ClNO₂S	Z = 4
M_r = 281.75	F(000) = 584
Triclinic, P1	D_x = 1.395 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.609 (1) Å	Cell parameters from 25 reflections
b = 11.143 (1) Å	θ = 5.6–21.8°
c = 14.726 (2) Å	µ = 3.93 mm⁻¹
α = 98.618 (7)°	T = 299 K
β = 90.951 (8)°	Prism, colourless
γ = 105.79 (1)°	0.33 × 0.23 × 0.08 mm
V = 1341.6 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2980 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 67.0°, θ_min = 3.0°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
T_min = 0.350, T_max = 0.729	l = −17→7
7620 measured reflections	3 standard reflections every 120 min
4784 independent reflections	intensity decay: 1.0%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0962P)² + 0.1233P] where P = (F_o² + 2F_c²)/3
4784 reflections	(Δ/σ)_max = 0.005
333 parameters	Δρ_max = 0.41 e Å⁻³
12 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₃H₁₂ClNO₂S	γ = 105.79 (1)°
M_r = 281.75	V = 1341.6 (3) Å³
Triclinic, P1	Z = 4
a = 8.609 (1) Å	Cu Kα radiation
b = 11.143 (1) Å	µ = 3.93 mm⁻¹
c = 14.726 (2) Å	T = 299 K
α = 98.618 (7)°	0.33 × 0.23 × 0.08 mm
β = 90.951 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2980 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.350, T_max = 0.729	3 standard reflections every 120 min
7620 measured reflections	intensity decay: 1.0%
4784 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	12 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.41 e Å⁻³
4784 reflections	Δρ_min = −0.42 e Å⁻³
333 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	0.4618 (4)	0.43860 (18)	0.24063 (15)	0.1670 (10)
S1	0.46343 (11)	0.96896 (11)	0.15504 (7)	0.0586 (3)
O1	0.4383 (4)	1.0364 (3)	0.2403 (2)	0.0802 (9)
O2	0.3532 (3)	0.9562 (3)	0.07717 (19)	0.0722 (8)
N1	0.6377 (4)	1.0345 (3)	0.1199 (2)	0.0611 (9)
H1N	0.647 (5)	1.039 (4)	0.059 (3)	0.073*
C1	0.4664 (4)	0.8182 (4)	0.1749 (3)	0.0565 (10)
C2	0.4758 (8)	0.7240 (5)	0.1044 (3)	0.0907 (16)
C3	0.4778 (10)	0.6088 (5)	0.1273 (4)	0.120 (2)
H3	0.4876	0.5444	0.0816	0.144*
C4	0.4653 (7)	0.5877 (5)	0.2179 (4)	0.0910 (16)
C5	0.4560 (6)	0.6791 (5)	0.2862 (3)	0.0768 (13)
H5	0.4494	0.6642	0.3467	0.092*
C6	0.4563 (5)	0.7946 (5)	0.2653 (3)	0.0663 (11)
H6	0.4495	0.8586	0.3122	0.080*
C7	0.7894 (4)	1.0635 (3)	0.1698 (3)	0.0522 (9)
C8	0.9247 (5)	1.0883 (4)	0.1201 (3)	0.0701 (12)
H8	0.9151	1.0848	0.0567	0.084*
C9	1.0763 (6)	1.1187 (5)	0.1656 (4)	0.0865 (15)
H9	1.1685	1.1358	0.1323	0.104*
C10	1.0914 (6)	1.1239 (5)	0.2591 (4)	0.0834 (15)
H10	1.1933	1.1440	0.2891	0.100*
C11	0.9570 (6)	1.0995 (4)	0.3074 (3)	0.0718 (12)
H11	0.9671	1.1026	0.3707	0.086*
C12	0.8054 (5)	1.0701 (4)	0.2639 (3)	0.0653 (11)
H12	0.7141	1.0547	0.2980	0.078*
C13	0.4894 (9)	0.7419 (4)	0.0007 (3)	0.102 (2)
H13A	0.5834	0.8097	−0.0050	0.123*
H13B	0.3947	0.7616	−0.0205	0.123*
H13C	0.4985	0.6653	−0.0357	0.123*
Cl2	0.1160 (4)	0.3570 (3)	0.99174 (14)	0.1919 (12)
S2	−0.06931 (11)	0.32374 (9)	0.57752 (8)	0.0560 (3)
O3	−0.1468 (3)	0.4185 (3)	0.5635 (2)	0.0703 (8)
O4	−0.1553 (3)	0.1953 (3)	0.5486 (2)	0.0727 (8)
N2	0.0946 (4)	0.3586 (3)	0.5248 (2)	0.0581 (9)
H2N	0.114 (5)	0.431 (4)	0.503 (3)	0.070*
C14	−0.0126 (5)	0.3404 (4)	0.6948 (3)	0.0569 (10)
C15	0.0592 (7)	0.4573 (4)	0.7478 (4)	0.0803 (13)
C16	0.0983 (8)	0.4591 (6)	0.8395 (4)	0.115 (2)
H16	0.1457	0.5359	0.8770	0.138*
C17	0.0679 (8)	0.3489 (7)	0.8762 (4)	0.110 (2)
C18	−0.0041 (7)	0.2348 (6)	0.8243 (4)	0.0906 (16)
H18	−0.0267	0.1612	0.8502	0.109*
C19	−0.0424 (5)	0.2309 (4)	0.7334 (3)	0.0679 (11)
H19	−0.0894	0.1533	0.6967	0.081*
C20	0.2114 (4)	0.2902 (3)	0.5100 (2)	0.0477 (8)
C21	0.1911 (5)	0.1719 (4)	0.5338 (3)	0.0610 (10)
H21	0.0998	0.1346	0.5632	0.073*
C22	0.3085 (6)	0.1093 (4)	0.5135 (3)	0.0692 (12)
H22	0.2954	0.0292	0.5286	0.083*
C23	0.4443 (6)	0.1657 (5)	0.4708 (3)	0.0742 (13)
H23	0.5231	0.1238	0.4574	0.089*
C24	0.4630 (5)	0.2827 (5)	0.4484 (3)	0.0723 (12)
H24	0.5551	0.3209	0.4201	0.087*
C25	0.3464 (4)	0.3451 (4)	0.4674 (3)	0.0577 (10)
H25	0.3596	0.4247	0.4513	0.069*
C26	0.0961 (9)	0.5821 (4)	0.7100 (4)	0.111 (2)
H26A	0.1530	0.5749	0.6548	0.133*
H26B	0.1619	0.6486	0.7550	0.133*
H26C	−0.0033	0.6010	0.6965	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.280 (3)	0.1079 (13)	0.1210 (15)	0.0456 (15)	0.0296 (16)	0.0575 (11)
S1	0.0529 (5)	0.0868 (7)	0.0417 (5)	0.0282 (5)	0.0004 (4)	0.0114 (5)
O1	0.092 (2)	0.114 (3)	0.0494 (17)	0.0576 (19)	0.0072 (15)	0.0056 (16)
O2	0.0544 (16)	0.121 (3)	0.0516 (17)	0.0361 (16)	−0.0077 (13)	0.0244 (16)
N1	0.0573 (19)	0.085 (2)	0.0421 (18)	0.0178 (17)	−0.0045 (15)	0.0176 (17)
C1	0.052 (2)	0.076 (3)	0.039 (2)	0.0125 (18)	0.0021 (16)	0.0133 (18)
C2	0.146 (5)	0.079 (3)	0.047 (3)	0.030 (3)	0.012 (3)	0.017 (2)
C3	0.230 (8)	0.074 (3)	0.057 (3)	0.036 (4)	0.021 (4)	0.018 (3)
C4	0.123 (4)	0.081 (3)	0.066 (3)	0.017 (3)	0.006 (3)	0.025 (3)
C5	0.082 (3)	0.098 (4)	0.053 (3)	0.018 (3)	0.012 (2)	0.030 (3)
C6	0.059 (2)	0.091 (3)	0.048 (2)	0.015 (2)	0.0018 (19)	0.018 (2)
C7	0.057 (2)	0.051 (2)	0.049 (2)	0.0156 (17)	−0.0071 (17)	0.0100 (16)
C8	0.062 (3)	0.088 (3)	0.062 (3)	0.026 (2)	0.003 (2)	0.009 (2)
C9	0.058 (3)	0.112 (4)	0.089 (4)	0.024 (3)	0.002 (3)	0.012 (3)
C10	0.070 (3)	0.080 (3)	0.096 (4)	0.025 (2)	−0.029 (3)	−0.001 (3)
C11	0.081 (3)	0.063 (3)	0.065 (3)	0.012 (2)	−0.025 (2)	0.010 (2)
C12	0.065 (3)	0.074 (3)	0.050 (2)	0.007 (2)	−0.0075 (19)	0.015 (2)
C13	0.226 (7)	0.068 (3)	0.026 (2)	0.061 (4)	0.018 (3)	0.0116 (19)
Cl2	0.244 (3)	0.239 (3)	0.0830 (12)	0.035 (2)	−0.0157 (15)	0.0602 (15)
S2	0.0490 (5)	0.0529 (5)	0.0731 (7)	0.0173 (4)	0.0041 (4)	0.0259 (5)
O3	0.0608 (16)	0.0743 (19)	0.095 (2)	0.0364 (14)	0.0125 (15)	0.0398 (16)
O4	0.0641 (17)	0.0545 (17)	0.097 (2)	0.0071 (13)	−0.0088 (16)	0.0213 (15)
N2	0.0595 (19)	0.0517 (19)	0.078 (2)	0.0282 (16)	0.0181 (17)	0.0319 (17)
C14	0.057 (2)	0.055 (2)	0.066 (3)	0.0187 (18)	0.0156 (19)	0.0258 (19)
C15	0.103 (4)	0.063 (3)	0.073 (3)	0.019 (3)	0.007 (3)	0.015 (2)
C16	0.152 (6)	0.096 (4)	0.081 (4)	0.010 (4)	0.001 (4)	0.009 (3)
C17	0.131 (5)	0.131 (6)	0.071 (4)	0.027 (4)	0.003 (4)	0.041 (4)
C18	0.093 (4)	0.103 (4)	0.089 (4)	0.029 (3)	0.011 (3)	0.053 (3)
C19	0.070 (3)	0.063 (3)	0.079 (3)	0.021 (2)	0.007 (2)	0.032 (2)
C20	0.053 (2)	0.0466 (19)	0.046 (2)	0.0183 (16)	−0.0057 (16)	0.0085 (15)
C21	0.062 (2)	0.057 (2)	0.070 (3)	0.0214 (19)	0.001 (2)	0.019 (2)
C22	0.081 (3)	0.057 (2)	0.076 (3)	0.032 (2)	−0.010 (2)	0.008 (2)
C23	0.076 (3)	0.089 (3)	0.070 (3)	0.051 (3)	−0.004 (2)	0.001 (2)
C24	0.063 (3)	0.087 (3)	0.078 (3)	0.032 (2)	0.015 (2)	0.024 (3)
C25	0.056 (2)	0.061 (2)	0.058 (2)	0.0166 (18)	−0.0001 (18)	0.0164 (19)
C26	0.171 (6)	0.045 (3)	0.104 (4)	0.007 (3)	−0.003 (4)	0.010 (3)

Geometric parameters (Å, º) top

Cl1—C4	1.735 (6)	Cl2—C17	1.727 (6)
S1—O1	1.415 (3)	S2—O4	1.417 (3)
S1—O2	1.441 (3)	S2—O3	1.431 (3)
S1—N1	1.611 (4)	S2—N2	1.604 (3)
S1—C1	1.754 (4)	S2—C14	1.756 (4)
N1—C7	1.419 (5)	N2—C20	1.419 (4)
N1—H1N	0.91 (5)	N2—H2N	0.88 (4)
C1—C2	1.382 (6)	C14—C19	1.385 (5)
C1—C6	1.395 (5)	C14—C15	1.389 (6)
C2—C3	1.380 (7)	C15—C16	1.383 (7)
C2—C13	1.571 (6)	C15—C26	1.529 (7)
C3—C4	1.390 (7)	C16—C17	1.378 (8)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.340 (7)	C17—C18	1.360 (8)
C5—C6	1.367 (6)	C18—C19	1.366 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.372 (5)	C20—C25	1.367 (5)
C7—C12	1.380 (5)	C20—C21	1.381 (5)
C8—C9	1.388 (6)	C21—C22	1.389 (5)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.372 (7)	C22—C23	1.379 (6)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.353 (7)	C23—C24	1.361 (6)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.377 (6)	C24—C25	1.378 (5)
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

O1—S1—O2	118.88 (18)	O4—S2—O3	118.30 (18)
O1—S1—N1	110.6 (2)	O4—S2—N2	110.14 (19)
O2—S1—N1	103.80 (17)	O3—S2—N2	104.50 (17)
O1—S1—C1	106.88 (19)	O4—S2—C14	107.02 (18)
O2—S1—C1	109.17 (19)	O3—S2—C14	109.55 (19)
N1—S1—C1	107.02 (18)	N2—S2—C14	106.81 (18)
C7—N1—S1	126.6 (3)	C20—N2—S2	128.7 (3)
C7—N1—H1N	113 (3)	C20—N2—H2N	116 (3)
S1—N1—H1N	119 (3)	S2—N2—H2N	115 (3)
C2—C1—C6	120.1 (4)	C19—C14—C15	120.7 (4)
C2—C1—S1	122.2 (3)	C19—C14—S2	117.1 (3)
C6—C1—S1	117.7 (3)	C15—C14—S2	122.3 (3)
C3—C2—C1	117.7 (4)	C16—C15—C14	117.3 (5)
C3—C2—C13	118.5 (4)	C16—C15—C26	119.1 (5)
C1—C2—C13	123.8 (4)	C14—C15—C26	123.6 (5)
C2—C3—C4	120.8 (5)	C17—C16—C15	121.0 (6)
C2—C3—H3	119.6	C17—C16—H16	119.5
C4—C3—H3	119.6	C15—C16—H16	119.5
C5—C4—C3	121.4 (5)	C18—C17—C16	121.4 (6)
C5—C4—Cl1	120.5 (4)	C18—C17—Cl2	119.5 (5)
C3—C4—Cl1	118.0 (4)	C16—C17—Cl2	119.1 (6)
C4—C5—C6	118.7 (4)	C17—C18—C19	118.4 (5)
C4—C5—H5	120.6	C17—C18—H18	120.8
C6—C5—H5	120.6	C19—C18—H18	120.8
C5—C6—C1	121.2 (4)	C18—C19—C14	121.1 (5)
C5—C6—H6	119.4	C18—C19—H19	119.4
C1—C6—H6	119.4	C14—C19—H19	119.4
C8—C7—C12	119.8 (4)	C25—C20—C21	120.2 (3)
C8—C7—N1	116.9 (4)	C25—C20—N2	116.9 (3)
C12—C7—N1	123.3 (4)	C21—C20—N2	123.0 (3)
C7—C8—C9	119.3 (4)	C20—C21—C22	119.3 (4)
C7—C8—H8	120.4	C20—C21—H21	120.4
C9—C8—H8	120.4	C22—C21—H21	120.4
C10—C9—C8	120.7 (5)	C23—C22—C21	120.1 (4)
C10—C9—H9	119.7	C23—C22—H22	120.0
C8—C9—H9	119.7	C21—C22—H22	120.0
C11—C10—C9	119.5 (4)	C24—C23—C22	119.9 (4)
C11—C10—H10	120.2	C24—C23—H23	120.1
C9—C10—H10	120.2	C22—C23—H23	120.1
C10—C11—C12	120.9 (4)	C23—C24—C25	120.5 (4)
C10—C11—H11	119.6	C23—C24—H24	119.7
C12—C11—H11	119.6	C25—C24—H24	119.7
C11—C12—C7	119.9 (4)	C20—C25—C24	120.1 (4)
C11—C12—H12	120.1	C20—C25—H25	119.9
C7—C12—H12	120.1	C24—C25—H25	119.9
C2—C13—H13A	109.5	C15—C26—H26A	109.5
C2—C13—H13B	109.5	C15—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C2—C13—H13C	109.5	C15—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5

O1—S1—N1—C7	54.0 (4)	O4—S2—N2—C20	−46.3 (4)
O2—S1—N1—C7	−177.4 (3)	O3—S2—N2—C20	−174.3 (3)
C1—S1—N1—C7	−62.0 (4)	C14—S2—N2—C20	69.6 (4)
O1—S1—C1—C2	174.7 (4)	O4—S2—C14—C19	6.9 (4)
O2—S1—C1—C2	44.9 (5)	O3—S2—C14—C19	136.3 (3)
N1—S1—C1—C2	−66.8 (4)	N2—S2—C14—C19	−111.1 (3)
O1—S1—C1—C6	−4.2 (4)	O4—S2—C14—C15	−173.1 (4)
O2—S1—C1—C6	−134.0 (3)	O3—S2—C14—C15	−43.7 (4)
N1—S1—C1—C6	114.2 (3)	N2—S2—C14—C15	68.9 (4)
C6—C1—C2—C3	−1.2 (8)	C19—C14—C15—C16	−0.3 (7)
S1—C1—C2—C3	179.9 (5)	S2—C14—C15—C16	179.7 (4)
C6—C1—C2—C13	−179.3 (5)	C19—C14—C15—C26	179.9 (5)
S1—C1—C2—C13	1.7 (8)	S2—C14—C15—C26	−0.1 (7)
C1—C2—C3—C4	2.1 (10)	C14—C15—C16—C17	0.5 (9)
C13—C2—C3—C4	−179.7 (6)	C26—C15—C16—C17	−179.6 (6)
C2—C3—C4—C5	−2.0 (11)	C15—C16—C17—C18	−1.3 (11)
C2—C3—C4—Cl1	177.8 (6)	C15—C16—C17—Cl2	−178.9 (5)
C3—C4—C5—C6	1.0 (9)	C16—C17—C18—C19	1.8 (10)
Cl1—C4—C5—C6	−178.9 (4)	Cl2—C17—C18—C19	179.4 (4)
C4—C5—C6—C1	−0.1 (7)	C17—C18—C19—C14	−1.5 (8)
C2—C1—C6—C5	0.3 (7)	C15—C14—C19—C18	0.8 (7)
S1—C1—C6—C5	179.2 (3)	S2—C14—C19—C18	−179.2 (4)
S1—N1—C7—C8	163.5 (3)	S2—N2—C20—C25	−176.1 (3)
S1—N1—C7—C12	−17.8 (6)	S2—N2—C20—C21	5.9 (6)
C12—C7—C8—C9	0.5 (6)	C25—C20—C21—C22	−0.5 (6)
N1—C7—C8—C9	179.2 (4)	N2—C20—C21—C22	177.4 (4)
C7—C8—C9—C10	0.1 (7)	C20—C21—C22—C23	0.7 (6)
C8—C9—C10—C11	−0.2 (8)	C21—C22—C23—C24	−0.2 (7)
C9—C10—C11—C12	−0.3 (7)	C22—C23—C24—C25	−0.5 (7)
C10—C11—C12—C7	0.9 (7)	C21—C20—C25—C24	−0.2 (6)
C8—C7—C12—C11	−1.0 (6)	N2—C20—C25—C24	−178.2 (4)
N1—C7—C12—C11	−179.7 (4)	C23—C24—C25—C20	0.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.91 (5)	2.02 (5)	2.922 (4)	175 (4)
N2—H2N···O3ⁱⁱ	0.88 (4)	2.03 (5)	2.906 (4)	173 (4)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂ClNO₂S
M_r	281.75
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.609 (1), 11.143 (1), 14.726 (2)
α, β, γ (°)	98.618 (7), 90.951 (8), 105.79 (1)
V (Å³)	1341.6 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.93
Crystal size (mm)	0.33 × 0.23 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.350, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	7620, 4784, 2980
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.176, 1.03
No. of reflections	4784
No. of parameters	333
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.42

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.91 (5)	2.02 (5)	2.922 (4)	175 (4)
N2—H2N···O3ⁱⁱ	0.88 (4)	2.03 (5)	2.906 (4)	173 (4)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z+1.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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