N-(3-Chloro­phen­yl)-4-nitro­benzene­sulfonamide

Chaithanya, U.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536812047496

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3424

doi:10.1107/S1600536812047496

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N-(3-Chlorophenyl)-4-nitrobenzenesulfonamide

U. Chaithanya,^a Sabine Foro ^b and B. Thimme Gowda ^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 16 November 2012; accepted 19 November 2012; online 24 November 2012)

There are two independent molecules in the asymmetric unit of the title compound, C₁₂H₉ClN₂O₄S, in which the dihedral angles between the planes of the benzene rings are 46.90 (14) and 44.50 (14)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into zigzag chains parallel to the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012 ); Gowda et al. (2002 ) and of N-chloroarylamides, see: Gowda & Shetty (2004 ); Gowda & Weiss (1994 ); Shetty & Gowda (2004 ).

Experimental

Crystal data

C₁₂H₉ClN₂O₄S
M_r = 312.72
Monoclinic, P 2₁ /n
a = 14.3419 (8) Å
b = 7.7579 (4) Å
c = 23.895 (1) Å
β = 90.345 (5)°
V = 2658.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.48 × 0.40 × 0.20 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 = 0.810, T_max = 0.914
9649 measured reflections
4839 independent reflections
3112 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.163
S = 1.05
4839 reflections
367 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N⋯O4ⁱ	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536812047496/bt6857sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047496/bt6857Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047496/bt6857Isup3.cml

checkCIF report

Comment top

As a part of studying the effect of substituents on the structures and other aspects of N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylamides (Gowda & Shetty, 2004; Gowda & Weiss, 1994; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(3-chlorophenyl)-4-nitrobenzenesulfonamide (I) has been determined (Fig. 1). The asymmetric unit of the structure contains two independent molecules. The N—C bonds in the C—SO₂—NH—C segments have gauche torsions with respect to the S═O bonds.

The molecules in (I) are twisted at the S—N bonds with the torsional angles of -58.67 (30) and 61.49 (30)°, compared to the value of 48.46 (18)° in N-(3-chlorophenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012).

The dihedral angle between the sulfonyl and the anilino rings are 46.90 (14) and 44.50 (14)°, compared to the value of 73.65 (7)° in (II).

N—H···O hydrogen bonds link the molecules into zigzag chains parallel to the a-axis. (Table 1, Fig. 2.)

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroarylamides, see: Gowda & Shetty (2004); Gowda & Weiss (1994); Shetty & Gowda (2004).

Experimental top

The title compound was prepared by treating 4-nitrobenzenesulfonyl- chloride with 3-chloroaniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml).

The resultant solid N-(3-chlorophenyl)-4-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (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 with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(3-Chlorophenyl)-4-nitrobenzenesulfonamide top

Crystal data top

C₁₂H₉ClN₂O₄S	F(000) = 1280
M_r = 312.72	D_x = 1.563 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3273 reflections
a = 14.3419 (8) Å	θ = 2.6–27.8°
b = 7.7579 (4) Å	µ = 0.46 mm⁻¹
c = 23.895 (1) Å	T = 293 K
β = 90.345 (5)°	Prism, colourless
V = 2658.6 (2) Å³	0.48 × 0.40 × 0.20 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4839 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Rotation method data acquisition using ω scans	θ_max = 25.4°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→17
T_min = 0.810, T_max = 0.914	k = −9→5
9649 measured reflections	l = −27→28

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0682P)² + 2.2606P] where P = (F_o² + 2F_c²)/3
4839 reflections	(Δ/σ)_max = 0.009
367 parameters	Δρ_max = 0.83 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₂H₉ClN₂O₄S	V = 2658.6 (2) Å³
M_r = 312.72	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3419 (8) Å	µ = 0.46 mm⁻¹
b = 7.7579 (4) Å	T = 293 K
c = 23.895 (1) Å	0.48 × 0.40 × 0.20 mm
β = 90.345 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4839 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3112 reflections with I > 2σ(I)
T_min = 0.810, T_max = 0.914	R_int = 0.027
9649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.83 e Å⁻³
4839 reflections	Δρ_min = −0.29 e Å⁻³
367 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.09787 (10)	−0.35505 (17)	0.01810 (6)	0.0946 (5)
S1	0.16559 (6)	0.12543 (12)	0.20178 (4)	0.0434 (3)
O1	0.11688 (19)	−0.0333 (3)	0.20733 (11)	0.0562 (7)
O2	0.22431 (18)	0.1878 (4)	0.24582 (11)	0.0627 (8)
O3	−0.1904 (2)	0.6207 (4)	0.12567 (15)	0.0788 (10)
O4	−0.0928 (2)	0.8146 (4)	0.14880 (15)	0.0823 (10)
N1	0.23212 (19)	0.1114 (4)	0.14670 (14)	0.0452 (8)
H1N	0.272 (2)	0.194 (4)	0.1439 (15)	0.054*
N2	−0.1143 (2)	0.6643 (5)	0.14311 (14)	0.0566 (9)
C1	0.0817 (2)	0.2853 (4)	0.18560 (14)	0.0353 (8)
C2	0.1026 (2)	0.4570 (4)	0.19499 (15)	0.0423 (9)
H2	0.1599	0.4877	0.2104	0.051*
C3	0.0387 (2)	0.5819 (4)	0.18147 (15)	0.0442 (9)
H3	0.0514	0.6978	0.1878	0.053*
C4	−0.0450 (2)	0.5309 (4)	0.15819 (14)	0.0405 (8)
C5	−0.0679 (2)	0.3612 (5)	0.14868 (16)	0.0500 (10)
H5	−0.1253	0.3313	0.1332	0.060*
C6	−0.0030 (2)	0.2365 (5)	0.16275 (16)	0.0469 (9)
H6	−0.0163	0.1205	0.1569	0.056*
C7	0.1911 (2)	0.0681 (5)	0.09334 (15)	0.0413 (9)
C8	0.1675 (2)	−0.1024 (5)	0.08276 (17)	0.0482 (10)
H8	0.1777	−0.1874	0.1095	0.058*
C9	0.1285 (3)	−0.1422 (5)	0.03155 (18)	0.0544 (10)
C10	0.1144 (3)	−0.0199 (7)	−0.00864 (18)	0.0658 (12)
H10	0.0883	−0.0494	−0.0431	0.079*
C11	0.1395 (3)	0.1489 (6)	0.00264 (18)	0.0668 (12)
H11	0.1305	0.2334	−0.0245	0.080*
C12	0.1773 (3)	0.1921 (5)	0.05326 (17)	0.0549 (10)
H12	0.1937	0.3058	0.0606	0.066*
Cl2	0.61875 (14)	1.53899 (18)	0.02541 (7)	0.1192 (6)
S2	0.66256 (6)	1.03064 (12)	0.20747 (4)	0.0478 (3)
O5	0.61482 (19)	1.1899 (3)	0.21387 (12)	0.0583 (7)
O6	0.72154 (19)	0.9650 (4)	0.25102 (12)	0.0703 (9)
O7	0.3061 (2)	0.5453 (4)	0.12695 (15)	0.0789 (10)
O8	0.4020 (2)	0.3483 (4)	0.15000 (17)	0.0907 (11)
N3	0.7282 (2)	1.0461 (4)	0.15232 (15)	0.0503 (8)
H3N	0.762 (2)	0.958 (4)	0.1481 (16)	0.060*
N4	0.3811 (2)	0.4986 (5)	0.14497 (14)	0.0568 (9)
C13	0.5779 (2)	0.8725 (4)	0.19141 (14)	0.0373 (8)
C14	0.5992 (2)	0.6997 (5)	0.19794 (16)	0.0470 (9)
H14	0.6570	0.6670	0.2122	0.056*
C15	0.5345 (2)	0.5764 (5)	0.18336 (16)	0.0486 (10)
H15	0.5474	0.4598	0.1880	0.058*
C16	0.4501 (2)	0.6303 (5)	0.16172 (15)	0.0421 (9)
C17	0.4269 (2)	0.8010 (5)	0.15583 (15)	0.0464 (9)
H17	0.3685	0.8331	0.1423	0.056*
C18	0.4919 (2)	0.9235 (5)	0.17029 (15)	0.0437 (9)
H18	0.4783	1.0400	0.1660	0.052*
C19	0.6866 (2)	1.0996 (5)	0.10019 (16)	0.0448 (9)
C20	0.6731 (3)	1.2725 (5)	0.08980 (18)	0.0516 (10)
H20	0.6901	1.3547	0.1163	0.062*
C21	0.6343 (3)	1.3211 (5)	0.0398 (2)	0.0633 (12)
C22	0.6084 (3)	1.2024 (6)	0.00016 (19)	0.0672 (12)
H22	0.5809	1.2385	−0.0332	0.081*
C23	0.6231 (3)	1.0320 (6)	0.0097 (2)	0.0692 (13)
H23	0.6067	0.9511	−0.0173	0.083*
C24	0.6630 (3)	0.9787 (5)	0.06058 (19)	0.0592 (11)
H24	0.6734	0.8623	0.0674	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1078 (11)	0.0610 (8)	0.1148 (11)	−0.0144 (7)	−0.0227 (9)	−0.0310 (8)
S1	0.0416 (5)	0.0361 (5)	0.0524 (6)	0.0073 (4)	−0.0107 (4)	0.0001 (4)
O1	0.0621 (17)	0.0330 (15)	0.0736 (19)	0.0044 (13)	0.0006 (14)	0.0137 (13)
O2	0.0595 (17)	0.0634 (19)	0.0648 (18)	0.0187 (15)	−0.0274 (14)	−0.0094 (15)
O3	0.0481 (18)	0.075 (2)	0.113 (3)	0.0106 (16)	−0.0208 (18)	0.0294 (19)
O4	0.087 (2)	0.0378 (18)	0.122 (3)	0.0197 (17)	−0.020 (2)	0.0079 (18)
N1	0.0314 (16)	0.0350 (18)	0.069 (2)	−0.0020 (13)	−0.0051 (15)	−0.0042 (16)
N2	0.056 (2)	0.053 (2)	0.061 (2)	0.0157 (18)	0.0009 (17)	0.0160 (18)
C1	0.0341 (18)	0.0297 (19)	0.042 (2)	0.0035 (15)	−0.0032 (15)	−0.0025 (16)
C2	0.0317 (18)	0.038 (2)	0.057 (2)	−0.0035 (16)	−0.0079 (16)	−0.0043 (18)
C3	0.046 (2)	0.0253 (19)	0.061 (2)	−0.0012 (16)	−0.0008 (19)	0.0000 (17)
C4	0.0397 (19)	0.035 (2)	0.047 (2)	0.0074 (16)	0.0010 (16)	0.0079 (17)
C5	0.038 (2)	0.045 (2)	0.067 (3)	−0.0046 (17)	−0.0137 (18)	−0.002 (2)
C6	0.042 (2)	0.033 (2)	0.066 (3)	−0.0026 (17)	−0.0122 (19)	−0.0047 (18)
C7	0.0292 (18)	0.040 (2)	0.055 (2)	0.0028 (16)	0.0045 (16)	−0.0034 (18)
C8	0.043 (2)	0.037 (2)	0.065 (3)	0.0010 (17)	0.0002 (19)	0.0002 (19)
C9	0.046 (2)	0.050 (3)	0.066 (3)	−0.0033 (19)	0.001 (2)	−0.013 (2)
C10	0.061 (3)	0.083 (4)	0.053 (3)	0.007 (3)	−0.002 (2)	−0.009 (3)
C11	0.074 (3)	0.069 (3)	0.057 (3)	0.007 (3)	0.001 (2)	0.013 (2)
C12	0.059 (3)	0.042 (2)	0.063 (3)	0.001 (2)	0.007 (2)	0.002 (2)
Cl2	0.1649 (16)	0.0543 (8)	0.1379 (14)	−0.0001 (9)	−0.0415 (12)	0.0214 (9)
S2	0.0420 (5)	0.0396 (6)	0.0615 (6)	−0.0079 (4)	−0.0109 (5)	−0.0029 (5)
O5	0.0621 (17)	0.0346 (15)	0.0783 (19)	−0.0044 (13)	0.0024 (14)	−0.0155 (14)
O6	0.0623 (18)	0.072 (2)	0.0765 (19)	−0.0191 (16)	−0.0324 (16)	0.0079 (16)
O7	0.0486 (17)	0.076 (2)	0.112 (3)	−0.0156 (16)	−0.0221 (18)	−0.0165 (19)
O8	0.083 (2)	0.0390 (19)	0.150 (3)	−0.0190 (17)	−0.019 (2)	−0.006 (2)
N3	0.0324 (17)	0.0358 (19)	0.083 (2)	0.0028 (13)	−0.0023 (16)	0.0026 (17)
N4	0.052 (2)	0.050 (2)	0.068 (2)	−0.0148 (18)	−0.0021 (18)	−0.0091 (19)
C13	0.0332 (18)	0.0322 (19)	0.046 (2)	0.0006 (15)	−0.0018 (15)	−0.0003 (16)
C14	0.037 (2)	0.041 (2)	0.063 (2)	0.0035 (17)	−0.0058 (18)	0.0061 (19)
C15	0.045 (2)	0.030 (2)	0.071 (3)	0.0015 (17)	0.002 (2)	0.0024 (18)
C16	0.0378 (19)	0.039 (2)	0.049 (2)	−0.0060 (17)	0.0010 (17)	−0.0050 (17)
C17	0.0353 (19)	0.045 (2)	0.058 (2)	0.0016 (17)	−0.0088 (17)	−0.0015 (19)
C18	0.043 (2)	0.0287 (19)	0.060 (2)	0.0035 (16)	−0.0083 (18)	0.0019 (17)
C19	0.0335 (19)	0.039 (2)	0.062 (3)	−0.0053 (16)	0.0090 (18)	0.0008 (19)
C20	0.046 (2)	0.034 (2)	0.075 (3)	−0.0039 (17)	−0.001 (2)	−0.001 (2)
C21	0.066 (3)	0.043 (2)	0.082 (3)	−0.003 (2)	0.000 (2)	0.013 (2)
C22	0.071 (3)	0.064 (3)	0.066 (3)	−0.005 (3)	−0.006 (2)	0.001 (3)
C23	0.071 (3)	0.064 (3)	0.073 (3)	−0.011 (3)	0.011 (3)	−0.023 (3)
C24	0.057 (3)	0.041 (2)	0.080 (3)	−0.005 (2)	0.012 (2)	−0.012 (2)

Geometric parameters (Å, º) top

Cl1—C9	1.738 (4)	Cl2—C21	1.739 (4)
S1—O1	1.423 (3)	S2—O5	1.421 (3)
S1—O2	1.428 (3)	S2—O6	1.431 (3)
S1—N1	1.634 (3)	S2—N3	1.629 (3)
S1—C1	1.770 (3)	S2—C13	1.767 (3)
O3—N2	1.215 (4)	O7—N4	1.211 (4)
O4—N2	1.214 (4)	O8—N4	1.209 (4)
N1—C7	1.441 (5)	N3—C19	1.439 (5)
N1—H1N	0.865 (18)	N3—H3N	0.845 (18)
N2—C4	1.478 (4)	N4—C16	1.476 (4)
C1—C6	1.382 (4)	C13—C14	1.383 (5)
C1—C2	1.383 (5)	C13—C18	1.388 (5)
C2—C3	1.371 (5)	C14—C15	1.376 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.377 (5)	C15—C16	1.379 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.375 (5)	C16—C17	1.373 (5)
C5—C6	1.382 (5)	C17—C18	1.373 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C12	1.371 (5)	C19—C24	1.373 (5)
C7—C8	1.388 (5)	C19—C20	1.378 (5)
C8—C9	1.377 (5)	C20—C21	1.368 (6)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.364 (6)	C21—C22	1.371 (6)
C10—C11	1.384 (6)	C22—C23	1.358 (6)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.364 (6)	C23—C24	1.402 (6)
C11—H11	0.9300	C23—H23	0.9300
C12—H12	0.9300	C24—H24	0.9300

O1—S1—O2	120.83 (17)	O5—S2—O6	120.94 (18)
O1—S1—N1	107.88 (16)	O5—S2—N3	107.70 (17)
O2—S1—N1	105.75 (17)	O6—S2—N3	105.83 (18)
O1—S1—C1	107.07 (16)	O5—S2—C13	107.24 (16)
O2—S1—C1	108.70 (16)	O6—S2—C13	108.26 (17)
N1—S1—C1	105.68 (16)	N3—S2—C13	105.98 (16)
C7—N1—S1	119.4 (2)	C19—N3—S2	118.9 (2)
C7—N1—H1N	112 (3)	C19—N3—H3N	111 (3)
S1—N1—H1N	114 (3)	S2—N3—H3N	112 (3)
O3—N2—O4	122.2 (3)	O8—N4—O7	122.9 (3)
O3—N2—C4	119.4 (4)	O8—N4—C16	118.3 (3)
O4—N2—C4	118.4 (3)	O7—N4—C16	118.8 (4)
C6—C1—C2	121.2 (3)	C14—C13—C18	120.8 (3)
C6—C1—S1	119.3 (3)	C14—C13—S2	119.9 (3)
C2—C1—S1	119.5 (3)	C18—C13—S2	119.3 (3)
C3—C2—C1	119.9 (3)	C15—C14—C13	119.9 (3)
C3—C2—H2	120.1	C15—C14—H14	120.1
C1—C2—H2	120.1	C13—C14—H14	120.1
C2—C3—C4	118.1 (3)	C14—C15—C16	118.2 (3)
C2—C3—H3	120.9	C14—C15—H15	120.9
C4—C3—H3	120.9	C16—C15—H15	120.9
C5—C4—C3	123.2 (3)	C17—C16—C15	122.8 (3)
C5—C4—N2	118.0 (3)	C17—C16—N4	118.6 (3)
C3—C4—N2	118.7 (3)	C15—C16—N4	118.5 (3)
C4—C5—C6	118.0 (3)	C16—C17—C18	118.6 (3)
C4—C5—H5	121.0	C16—C17—H17	120.7
C6—C5—H5	121.0	C18—C17—H17	120.7
C1—C6—C5	119.5 (3)	C17—C18—C13	119.6 (3)
C1—C6—H6	120.2	C17—C18—H18	120.2
C5—C6—H6	120.2	C13—C18—H18	120.2
C12—C7—C8	120.5 (4)	C24—C19—C20	120.5 (4)
C12—C7—N1	120.7 (3)	C24—C19—N3	120.0 (4)
C8—C7—N1	118.8 (3)	C20—C19—N3	119.6 (4)
C9—C8—C7	118.2 (4)	C21—C20—C19	118.8 (4)
C9—C8—H8	120.9	C21—C20—H20	120.6
C7—C8—H8	120.9	C19—C20—H20	120.6
C10—C9—C8	121.8 (4)	C20—C21—C22	121.7 (4)
C10—C9—Cl1	119.6 (3)	C20—C21—Cl2	119.4 (4)
C8—C9—Cl1	118.6 (3)	C22—C21—Cl2	118.8 (4)
C9—C10—C11	118.9 (4)	C23—C22—C21	119.8 (4)
C9—C10—H10	120.5	C23—C22—H22	120.1
C11—C10—H10	120.5	C21—C22—H22	120.1
C12—C11—C10	120.4 (4)	C22—C23—C24	119.7 (4)
C12—C11—H11	119.8	C22—C23—H23	120.2
C10—C11—H11	119.8	C24—C23—H23	120.2
C11—C12—C7	120.1 (4)	C19—C24—C23	119.6 (4)
C11—C12—H12	119.9	C19—C24—H24	120.2
C7—C12—H12	119.9	C23—C24—H24	120.2

O1—S1—N1—C7	55.6 (3)	O5—S2—N3—C19	−53.0 (3)
O2—S1—N1—C7	−173.8 (3)	O6—S2—N3—C19	176.3 (3)
C1—S1—N1—C7	−58.7 (3)	C13—S2—N3—C19	61.5 (3)
O1—S1—C1—C6	−21.6 (3)	O5—S2—C13—C14	−162.2 (3)
O2—S1—C1—C6	−153.6 (3)	O6—S2—C13—C14	−30.2 (4)
N1—S1—C1—C6	93.2 (3)	N3—S2—C13—C14	83.0 (3)
O1—S1—C1—C2	159.7 (3)	O5—S2—C13—C18	20.2 (3)
O2—S1—C1—C2	27.6 (3)	O6—S2—C13—C18	152.3 (3)
N1—S1—C1—C2	−85.5 (3)	N3—S2—C13—C18	−94.6 (3)
C6—C1—C2—C3	−0.1 (6)	C18—C13—C14—C15	0.1 (6)
S1—C1—C2—C3	178.6 (3)	S2—C13—C14—C15	−177.5 (3)
C1—C2—C3—C4	−0.6 (5)	C13—C14—C15—C16	0.9 (6)
C2—C3—C4—C5	1.0 (6)	C14—C15—C16—C17	−2.1 (6)
C2—C3—C4—N2	−179.6 (3)	C14—C15—C16—N4	178.8 (3)
O3—N2—C4—C5	3.8 (5)	O8—N4—C16—C17	179.6 (4)
O4—N2—C4—C5	−176.4 (4)	O7—N4—C16—C17	−0.5 (5)
O3—N2—C4—C3	−175.6 (4)	O8—N4—C16—C15	−1.3 (5)
O4—N2—C4—C3	4.2 (5)	O7—N4—C16—C15	178.6 (4)
C3—C4—C5—C6	−0.7 (6)	C15—C16—C17—C18	2.3 (6)
N2—C4—C5—C6	179.9 (3)	N4—C16—C17—C18	−178.6 (3)
C2—C1—C6—C5	0.4 (6)	C16—C17—C18—C13	−1.3 (6)
S1—C1—C6—C5	−178.3 (3)	C14—C13—C18—C17	0.2 (6)
C4—C5—C6—C1	0.0 (6)	S2—C13—C18—C17	177.7 (3)
S1—N1—C7—C12	104.1 (4)	S2—N3—C19—C24	−99.5 (4)
S1—N1—C7—C8	−77.1 (4)	S2—N3—C19—C20	82.3 (4)
C12—C7—C8—C9	−1.1 (5)	C24—C19—C20—C21	1.2 (6)
N1—C7—C8—C9	−179.9 (3)	N3—C19—C20—C21	179.3 (3)
C7—C8—C9—C10	1.1 (6)	C19—C20—C21—C22	0.3 (6)
C7—C8—C9—Cl1	−179.5 (3)	C19—C20—C21—Cl2	−178.8 (3)
C8—C9—C10—C11	−0.4 (6)	C20—C21—C22—C23	−1.5 (7)
Cl1—C9—C10—C11	−179.8 (3)	Cl2—C21—C22—C23	177.6 (4)
C9—C10—C11—C12	−0.3 (7)	C21—C22—C23—C24	1.2 (7)
C10—C11—C12—C7	0.3 (6)	C20—C19—C24—C23	−1.4 (6)
C8—C7—C12—C11	0.4 (6)	N3—C19—C24—C23	−179.5 (3)
N1—C7—C12—C11	179.2 (3)	C22—C23—C24—C19	0.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O8	0.87 (2)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N···O4ⁱ	0.85 (2)	2.36 (2)	3.135 (4)	153 (4)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₉ClN₂O₄S
M_r	312.72
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.3419 (8), 7.7579 (4), 23.895 (1)
β (°)	90.345 (5)
V (Å³)	2658.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.48 × 0.40 × 0.20

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	0.810, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	9649, 4839, 3112
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.163, 1.05
No. of reflections	4839
No. of parameters	367
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)	0.83, −0.29

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···O8	0.865 (18)	2.22 (2)	3.052 (4)	163 (3)
N3—H3N···O4ⁱ	0.845 (18)	2.36 (2)	3.135 (4)	153 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under UGC–BSR one-time grant to faculty and the Department of Science and Technology, Government of India, New Delhi, for the research grant under its promotion of university research and scientific excellence programme.

References

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