organic compounds
N-(2,3-Dichlorophenyl)-2-nitrobenzenesulfonamide
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
In the title compound, C12H8Cl2N2O4S, the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. Further, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intramolecular bifurcated N—H⋯(O,O) hydrogen bond. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the molecules into inversion dimers with R22(8) motifs.
Related literature
For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; 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.
Supporting information
https://doi.org/10.1107/S1600536812048076/rz5027sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048076/rz5027Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812048076/rz5027Isup3.cml
The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with 2,3-dichloroaniline 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-(2,3-dichlorophenyl)-2-nitrobenzenesulfon- amide 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.
H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The amino H atom was freely refined with the N—H distance restrained to 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom.
As a part of studying the effect of substituents on the structures and other aspects of N-(aryl)-amides (Gowda et al., 1994); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylsulfonamides(Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the
of N-(2,3-dichlorophenyl)-2-nitrobenzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the anilino ring, compared to the syn conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring and anti conformation between the N—H bond and the ortho- and meta-methyl groups in the anilino ring observed in N-(2,3-dimethylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012).The molecule in (I) is twisted at the S—N bond with the torsion angle of 61.15 (18)°, compared to the values of -60.37 (30) and 58.81 (34)° in the two independent molecules of (II).
The dihedral angle between the sulfonyl and the anilino ring is 68.00 (6)°, compared to the values of 53.67 (8) and 56.99 (9)° in the two molecules of (II).
The amide H-atom showed bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring, generating S(7) motifs and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating inversion dimers (Table 1, Fig. 2.)
For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (1994), of N-arylsulfonamides, see: Chaithanya et al. (2012); Gowda et al. (2002) and of N-chloroaryl-sulfonamides, see: Gowda & Shetty (2004); Shetty & Gowda (2004).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
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).C12H8Cl2N2O4S | F(000) = 704 |
Mr = 347.16 | Dx = 1.609 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2186 reflections |
a = 8.2197 (5) Å | θ = 2.6–27.7° |
b = 15.863 (1) Å | µ = 0.61 mm−1 |
c = 11.0108 (6) Å | T = 293 K |
β = 93.450 (6)° | Prism, colourless |
V = 1433.09 (15) Å3 | 0.44 × 0.36 × 0.28 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2923 independent reflections |
Radiation source: fine-focus sealed tube | 2304 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
Rotation method data acquisition using ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −4→10 |
Tmin = 0.774, Tmax = 0.847 | k = −19→19 |
5760 measured reflections | l = −13→13 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0395P)2 + 0.7218P] where P = (Fo2 + 2Fc2)/3 |
2923 reflections | (Δ/σ)max = 0.002 |
193 parameters | Δρmax = 0.35 e Å−3 |
2 restraints | Δρmin = −0.34 e Å−3 |
C12H8Cl2N2O4S | V = 1433.09 (15) Å3 |
Mr = 347.16 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.2197 (5) Å | µ = 0.61 mm−1 |
b = 15.863 (1) Å | T = 293 K |
c = 11.0108 (6) Å | 0.44 × 0.36 × 0.28 mm |
β = 93.450 (6)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2923 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2304 reflections with I > 2σ(I) |
Tmin = 0.774, Tmax = 0.847 | Rint = 0.013 |
5760 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 2 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.35 e Å−3 |
2923 reflections | Δρmin = −0.34 e Å−3 |
193 parameters |
Experimental. Absorption correction: 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1808 (2) | 0.83051 (12) | 0.19670 (17) | 0.0339 (4) | |
C2 | 0.0312 (2) | 0.80943 (13) | 0.24194 (17) | 0.0376 (4) | |
C3 | 0.0199 (3) | 0.75308 (15) | 0.3365 (2) | 0.0494 (6) | |
H3 | −0.0814 | 0.7382 | 0.3631 | 0.059* | |
C4 | 0.1601 (3) | 0.71913 (15) | 0.3910 (2) | 0.0572 (6) | |
H4 | 0.1538 | 0.6820 | 0.4560 | 0.069* | |
C5 | 0.3075 (3) | 0.73969 (15) | 0.3501 (2) | 0.0576 (6) | |
H5 | 0.4017 | 0.7171 | 0.3883 | 0.069* | |
C6 | 0.3199 (3) | 0.79411 (14) | 0.2517 (2) | 0.0455 (5) | |
H6 | 0.4215 | 0.8060 | 0.2229 | 0.055* | |
C7 | 0.3264 (2) | 1.02271 (12) | 0.21739 (18) | 0.0352 (4) | |
C8 | 0.2745 (3) | 1.05973 (14) | 0.32373 (19) | 0.0410 (5) | |
C9 | 0.3880 (3) | 1.09390 (15) | 0.40794 (19) | 0.0474 (5) | |
C10 | 0.5515 (3) | 1.08976 (16) | 0.3900 (2) | 0.0573 (6) | |
H10 | 0.6272 | 1.1122 | 0.4473 | 0.069* | |
C11 | 0.6023 (3) | 1.05199 (16) | 0.2863 (2) | 0.0593 (7) | |
H11 | 0.7131 | 1.0487 | 0.2742 | 0.071* | |
C12 | 0.4916 (3) | 1.01906 (14) | 0.2003 (2) | 0.0459 (5) | |
H12 | 0.5280 | 0.9942 | 0.1304 | 0.055* | |
N1 | 0.2103 (2) | 0.99427 (11) | 0.12555 (16) | 0.0385 (4) | |
H1N | 0.116 (2) | 1.0115 (14) | 0.131 (2) | 0.046* | |
N2 | −0.1233 (2) | 0.84663 (14) | 0.19410 (17) | 0.0477 (5) | |
O1 | 0.37021 (19) | 0.88086 (10) | 0.03520 (14) | 0.0518 (4) | |
O2 | 0.0757 (2) | 0.89329 (10) | −0.01537 (13) | 0.0526 (4) | |
O3 | −0.1264 (2) | 0.92105 (13) | 0.16889 (19) | 0.0696 (5) | |
O4 | −0.2424 (2) | 0.80065 (14) | 0.18634 (18) | 0.0736 (6) | |
Cl1 | 0.06982 (8) | 1.06521 (6) | 0.34758 (7) | 0.0781 (3) | |
Cl2 | 0.32597 (10) | 1.14330 (5) | 0.53734 (6) | 0.0784 (3) | |
S1 | 0.21072 (6) | 0.89869 (3) | 0.07156 (4) | 0.03673 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0374 (10) | 0.0298 (10) | 0.0343 (9) | 0.0005 (8) | −0.0010 (8) | −0.0022 (8) |
C2 | 0.0400 (11) | 0.0381 (11) | 0.0346 (10) | −0.0017 (9) | 0.0028 (9) | −0.0032 (8) |
C3 | 0.0596 (14) | 0.0482 (13) | 0.0414 (12) | −0.0091 (11) | 0.0102 (11) | 0.0017 (10) |
C4 | 0.0835 (15) | 0.0432 (13) | 0.0435 (12) | −0.0079 (13) | −0.0078 (12) | 0.0094 (10) |
C5 | 0.0628 (13) | 0.0449 (14) | 0.0621 (15) | 0.0044 (11) | −0.0222 (11) | 0.0079 (11) |
C6 | 0.0398 (11) | 0.0391 (12) | 0.0563 (13) | 0.0009 (9) | −0.0080 (10) | 0.0007 (10) |
C7 | 0.0371 (10) | 0.0286 (10) | 0.0397 (10) | −0.0019 (8) | 0.0003 (8) | 0.0034 (8) |
C8 | 0.0383 (11) | 0.0430 (12) | 0.0421 (11) | −0.0025 (9) | 0.0058 (9) | 0.0006 (9) |
C9 | 0.0555 (14) | 0.0459 (13) | 0.0405 (11) | −0.0005 (11) | 0.0010 (10) | −0.0066 (10) |
C10 | 0.0496 (14) | 0.0566 (16) | 0.0637 (15) | −0.0016 (12) | −0.0136 (12) | −0.0145 (12) |
C11 | 0.0360 (12) | 0.0609 (16) | 0.0803 (18) | −0.0010 (11) | −0.0013 (12) | −0.0143 (14) |
C12 | 0.0404 (11) | 0.0445 (13) | 0.0531 (13) | −0.0006 (10) | 0.0059 (10) | −0.0082 (10) |
N1 | 0.0361 (9) | 0.0356 (10) | 0.0431 (9) | 0.0017 (8) | −0.0044 (8) | 0.0006 (8) |
N2 | 0.0357 (10) | 0.0632 (14) | 0.0450 (10) | 0.0018 (9) | 0.0068 (8) | −0.0006 (9) |
O1 | 0.0524 (9) | 0.0535 (10) | 0.0518 (9) | −0.0029 (8) | 0.0213 (8) | −0.0098 (7) |
O2 | 0.0637 (10) | 0.0515 (10) | 0.0406 (8) | −0.0080 (8) | −0.0149 (7) | 0.0003 (7) |
O3 | 0.0492 (10) | 0.0597 (12) | 0.0991 (14) | 0.0157 (9) | −0.0011 (10) | 0.0076 (11) |
O4 | 0.0416 (9) | 0.0996 (16) | 0.0790 (13) | −0.0178 (10) | −0.0019 (9) | 0.0072 (11) |
Cl1 | 0.0441 (4) | 0.1163 (7) | 0.0756 (5) | −0.0079 (4) | 0.0186 (3) | −0.0316 (4) |
Cl2 | 0.0881 (5) | 0.0950 (6) | 0.0527 (4) | −0.0046 (4) | 0.0083 (4) | −0.0295 (4) |
S1 | 0.0411 (3) | 0.0379 (3) | 0.0312 (2) | −0.0025 (2) | 0.0018 (2) | −0.0019 (2) |
C1—C6 | 1.387 (3) | C8—C9 | 1.386 (3) |
C1—C2 | 1.395 (3) | C8—Cl1 | 1.721 (2) |
C1—S1 | 1.780 (2) | C9—C10 | 1.371 (3) |
C2—C3 | 1.379 (3) | C9—Cl2 | 1.730 (2) |
C2—N2 | 1.469 (3) | C10—C11 | 1.376 (4) |
C3—C4 | 1.376 (3) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—C12 | 1.377 (3) |
C4—C5 | 1.358 (4) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C12—H12 | 0.9300 |
C5—C6 | 1.394 (3) | N1—S1 | 1.6287 (18) |
C5—H5 | 0.9300 | N1—H1N | 0.827 (16) |
C6—H6 | 0.9300 | N2—O3 | 1.213 (3) |
C7—C12 | 1.384 (3) | N2—O4 | 1.220 (2) |
C7—C8 | 1.399 (3) | O1—S1 | 1.4221 (16) |
C7—N1 | 1.422 (3) | O2—S1 | 1.4236 (16) |
C6—C1—C2 | 117.74 (19) | C10—C9—C8 | 120.7 (2) |
C6—C1—S1 | 116.24 (16) | C10—C9—Cl2 | 118.70 (18) |
C2—C1—S1 | 126.01 (15) | C8—C9—Cl2 | 120.55 (18) |
C3—C2—C1 | 121.7 (2) | C9—C10—C11 | 119.3 (2) |
C3—C2—N2 | 115.78 (19) | C9—C10—H10 | 120.4 |
C1—C2—N2 | 122.49 (18) | C11—C10—H10 | 120.4 |
C4—C3—C2 | 119.4 (2) | C12—C11—C10 | 121.0 (2) |
C4—C3—H3 | 120.3 | C12—C11—H11 | 119.5 |
C2—C3—H3 | 120.3 | C10—C11—H11 | 119.5 |
C5—C4—C3 | 120.1 (2) | C11—C12—C7 | 120.3 (2) |
C5—C4—H4 | 119.9 | C11—C12—H12 | 119.9 |
C3—C4—H4 | 119.9 | C7—C12—H12 | 119.9 |
C4—C5—C6 | 121.0 (2) | C7—N1—S1 | 122.60 (14) |
C4—C5—H5 | 119.5 | C7—N1—H1N | 115.9 (16) |
C6—C5—H5 | 119.5 | S1—N1—H1N | 110.9 (17) |
C1—C6—C5 | 120.0 (2) | O3—N2—O4 | 124.1 (2) |
C1—C6—H6 | 120.0 | O3—N2—C2 | 118.64 (19) |
C5—C6—H6 | 120.0 | O4—N2—C2 | 117.2 (2) |
C12—C7—C8 | 118.85 (19) | O1—S1—O2 | 119.54 (10) |
C12—C7—N1 | 120.83 (19) | O1—S1—N1 | 108.08 (10) |
C8—C7—N1 | 120.21 (18) | O2—S1—N1 | 106.41 (9) |
C9—C8—C7 | 119.83 (19) | O1—S1—C1 | 105.65 (10) |
C9—C8—Cl1 | 120.22 (17) | O2—S1—C1 | 110.21 (9) |
C7—C8—Cl1 | 119.92 (16) | N1—S1—C1 | 106.24 (9) |
C6—C1—C2—C3 | −1.3 (3) | Cl2—C9—C10—C11 | −178.8 (2) |
S1—C1—C2—C3 | 177.24 (17) | C9—C10—C11—C12 | 0.5 (4) |
C6—C1—C2—N2 | 177.51 (19) | C10—C11—C12—C7 | −0.6 (4) |
S1—C1—C2—N2 | −4.0 (3) | C8—C7—C12—C11 | −0.5 (3) |
C1—C2—C3—C4 | 2.6 (3) | N1—C7—C12—C11 | 175.6 (2) |
N2—C2—C3—C4 | −176.3 (2) | C12—C7—N1—S1 | 57.5 (3) |
C2—C3—C4—C5 | −1.4 (4) | C8—C7—N1—S1 | −126.45 (18) |
C3—C4—C5—C6 | −1.0 (4) | C3—C2—N2—O3 | 138.7 (2) |
C2—C1—C6—C5 | −1.1 (3) | C1—C2—N2—O3 | −40.2 (3) |
S1—C1—C6—C5 | −179.79 (18) | C3—C2—N2—O4 | −38.8 (3) |
C4—C5—C6—C1 | 2.3 (4) | C1—C2—N2—O4 | 142.3 (2) |
C12—C7—C8—C9 | 1.7 (3) | C7—N1—S1—O1 | −51.85 (19) |
N1—C7—C8—C9 | −174.38 (19) | C7—N1—S1—O2 | 178.59 (16) |
C12—C7—C8—Cl1 | 179.99 (17) | C7—N1—S1—C1 | 61.15 (18) |
N1—C7—C8—Cl1 | 3.9 (3) | C6—C1—S1—O1 | 16.35 (18) |
C7—C8—C9—C10 | −1.9 (3) | C2—C1—S1—O1 | −162.21 (17) |
Cl1—C8—C9—C10 | 179.9 (2) | C6—C1—S1—O2 | 146.80 (16) |
C7—C8—C9—Cl2 | 177.68 (17) | C2—C1—S1—O2 | −31.8 (2) |
Cl1—C8—C9—Cl2 | −0.6 (3) | C6—C1—S1—N1 | −98.31 (17) |
C8—C9—C10—C11 | 0.7 (4) | C2—C1—S1—N1 | 83.13 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.83 (2) | 2.48 (2) | 3.136 (2) | 137 (2) |
N1—H1N···O3 | 0.83 (2) | 2.51 (2) | 3.065 (3) | 125 (2) |
N1—H1N···Cl1 | 0.83 (2) | 2.58 (2) | 2.9858 (19) | 111 (2) |
Symmetry code: (i) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C12H8Cl2N2O4S |
Mr | 347.16 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.2197 (5), 15.863 (1), 11.0108 (6) |
β (°) | 93.450 (6) |
V (Å3) | 1433.09 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.61 |
Crystal size (mm) | 0.44 × 0.36 × 0.28 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.774, 0.847 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5760, 2923, 2304 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.092, 1.01 |
No. of reflections | 2923 |
No. of parameters | 193 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.34 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.827 (16) | 2.48 (2) | 3.136 (2) | 137 (2) |
N1—H1N···O3 | 0.827 (16) | 2.51 (2) | 3.065 (3) | 125 (2) |
N1—H1N···Cl1 | 0.827 (16) | 2.58 (2) | 2.9858 (19) | 111.4 (18) |
Symmetry code: (i) −x, −y+2, −z. |
Acknowledgements
BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the 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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As a part of studying the effect of substituents on the structures and other aspects of N-(aryl)-amides (Gowda et al., 1994); N-arylsulfonamides (Chaithanya et al., 2012; Gowda et al., 2002) and N-chloroarylsulfonamides(Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2,3-dichlorophenyl)-2-nitrobenzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the anilino ring, compared to the syn conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring and anti conformation between the N—H bond and the ortho- and meta-methyl groups in the anilino ring observed in N-(2,3-dimethylphenyl)-2-nitrobenzenesulfonamide (II) (Chaithanya et al., 2012).
The molecule in (I) is twisted at the S—N bond with the torsion angle of 61.15 (18)°, compared to the values of -60.37 (30) and 58.81 (34)° in the two independent molecules of (II).
The dihedral angle between the sulfonyl and the anilino ring is 68.00 (6)°, compared to the values of 53.67 (8) and 56.99 (9)° in the two molecules of (II).
The amide H-atom showed bifurcated intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring, generating S(7) motifs and the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating inversion dimers (Table 1, Fig. 2.)