organic compounds
N-(2,5-Dimethylphenyl)-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 14H14N2O4S, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N—H⋯Osulfonamide hydrogen bonds link the molecules into inversion dimers.
of the title compound, CRelated 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-chloroarylsulfonamides, 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
10.1107/S1600536812047630/rz5026sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047630/rz5026Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047630/rz5026Isup3.cml
The title compound was prepared by treating 2-nitrobenzenesulfonyl- chloride with 2,5-dimethylaniline 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-(2,5-dimethylphenyl)-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 light brown 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, methyl C—H = 0.96 Å. The amino H atoms were 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(C-aromatic, N) and 1.5 Ueq (C-methyl) of the parent atom.
The (0 1 1) reflection is probably affected by the beamstop and was omitted from the refinement.
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).C14H14N2O4S | Z = 2 |
Mr = 306.33 | F(000) = 320 |
Triclinic, P1 | Dx = 1.364 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1987 (7) Å | Cell parameters from 3120 reflections |
b = 9.6729 (9) Å | θ = 2.6–27.8° |
c = 9.9328 (9) Å | µ = 0.23 mm−1 |
α = 84.386 (9)° | T = 293 K |
β = 72.096 (8)° | Prism, light brown |
γ = 89.239 (9)° | 0.36 × 0.24 × 0.16 mm |
V = 745.86 (12) Å3 |
Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD | 3027 independent reflections |
Radiation source: fine-focus sealed tube | 2629 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Rotation method data acquisition using ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −10→10 |
Tmin = 0.921, Tmax = 0.964 | k = −12→11 |
4954 measured reflections | l = −12→10 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0379P)2 + 0.3685P] where P = (Fo2 + 2Fc2)/3 |
3027 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.28 e Å−3 |
1 restraint | Δρmin = −0.29 e Å−3 |
C14H14N2O4S | γ = 89.239 (9)° |
Mr = 306.33 | V = 745.86 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1987 (7) Å | Mo Kα radiation |
b = 9.6729 (9) Å | µ = 0.23 mm−1 |
c = 9.9328 (9) Å | T = 293 K |
α = 84.386 (9)° | 0.36 × 0.24 × 0.16 mm |
β = 72.096 (8)° |
Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD | 3027 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2629 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.964 | Rint = 0.011 |
4954 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.28 e Å−3 |
3027 reflections | Δρmin = −0.29 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 | 0.3540 (2) | 0.0929 (2) | 0.6857 (2) | 0.0387 (4) | |
C2 | 0.4684 (2) | 0.0253 (2) | 0.7467 (2) | 0.0433 (4) | |
C3 | 0.6437 (3) | 0.0467 (3) | 0.6890 (3) | 0.0561 (6) | |
H3 | 0.7187 | −0.0016 | 0.7294 | 0.067* | |
C4 | 0.7051 (3) | 0.1400 (3) | 0.5713 (3) | 0.0657 (7) | |
H4 | 0.8226 | 0.1564 | 0.5326 | 0.079* | |
C5 | 0.5947 (3) | 0.2092 (3) | 0.5104 (3) | 0.0657 (7) | |
H5 | 0.6376 | 0.2732 | 0.4313 | 0.079* | |
C6 | 0.4199 (3) | 0.1846 (2) | 0.5655 (2) | 0.0525 (5) | |
H6 | 0.3462 | 0.2299 | 0.5216 | 0.063* | |
C7 | 0.0552 (3) | 0.3225 (2) | 0.8314 (2) | 0.0448 (5) | |
C8 | 0.1732 (3) | 0.4106 (2) | 0.8577 (2) | 0.0567 (6) | |
C9 | 0.1583 (4) | 0.5520 (3) | 0.8214 (3) | 0.0760 (8) | |
H9 | 0.2318 | 0.6147 | 0.8398 | 0.091* | |
C10 | 0.0386 (4) | 0.6010 (3) | 0.7595 (3) | 0.0772 (9) | |
H10 | 0.0348 | 0.6961 | 0.7352 | 0.093* | |
C11 | −0.0768 (4) | 0.5141 (3) | 0.7317 (3) | 0.0701 (7) | |
C12 | −0.0680 (3) | 0.3728 (2) | 0.7717 (2) | 0.0546 (5) | |
H12 | −0.1464 | 0.3114 | 0.7580 | 0.065* | |
C13 | 0.3075 (4) | 0.3582 (3) | 0.9231 (3) | 0.0808 (9) | |
H13A | 0.3794 | 0.2942 | 0.8642 | 0.121* | |
H13B | 0.2531 | 0.3118 | 1.0159 | 0.121* | |
H13C | 0.3759 | 0.4350 | 0.9310 | 0.121* | |
C14 | −0.2091 (5) | 0.5675 (4) | 0.6626 (4) | 0.1074 (12) | |
H14A | −0.1524 | 0.6151 | 0.5709 | 0.161* | |
H14B | −0.2833 | 0.6304 | 0.7213 | 0.161* | |
H14C | −0.2756 | 0.4907 | 0.6518 | 0.161* | |
N1 | 0.0568 (2) | 0.17583 (17) | 0.86856 (18) | 0.0440 (4) | |
H1N | 0.054 (3) | 0.147 (2) | 0.9500 (18) | 0.053* | |
N2 | 0.4089 (3) | −0.0701 (2) | 0.8773 (2) | 0.0605 (5) | |
O1 | 0.06849 (18) | 0.11008 (16) | 0.63232 (16) | 0.0524 (4) | |
O2 | 0.09053 (18) | −0.06778 (14) | 0.82168 (17) | 0.0530 (4) | |
O3 | 0.3174 (2) | −0.0226 (2) | 0.98338 (19) | 0.0766 (6) | |
O4 | 0.4595 (3) | −0.1884 (2) | 0.8720 (3) | 0.1039 (8) | |
S1 | 0.12780 (6) | 0.06923 (5) | 0.75061 (5) | 0.04028 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0295 (9) | 0.0461 (10) | 0.0427 (10) | 0.0008 (7) | −0.0130 (8) | −0.0090 (8) |
C2 | 0.0392 (10) | 0.0489 (11) | 0.0462 (11) | 0.0018 (8) | −0.0184 (8) | −0.0087 (9) |
C3 | 0.0352 (10) | 0.0803 (16) | 0.0610 (14) | 0.0081 (10) | −0.0235 (10) | −0.0184 (12) |
C4 | 0.0340 (11) | 0.107 (2) | 0.0540 (13) | −0.0084 (12) | −0.0080 (10) | −0.0155 (13) |
C5 | 0.0470 (12) | 0.0948 (19) | 0.0483 (13) | −0.0161 (12) | −0.0074 (10) | 0.0054 (12) |
C6 | 0.0427 (11) | 0.0664 (14) | 0.0482 (12) | −0.0028 (10) | −0.0159 (9) | 0.0026 (10) |
C7 | 0.0419 (10) | 0.0408 (10) | 0.0425 (10) | −0.0039 (8) | 0.0003 (8) | −0.0034 (8) |
C8 | 0.0508 (12) | 0.0569 (13) | 0.0516 (12) | −0.0120 (10) | 0.0032 (10) | −0.0149 (10) |
C9 | 0.0778 (18) | 0.0586 (16) | 0.0737 (18) | −0.0236 (14) | 0.0073 (15) | −0.0178 (13) |
C10 | 0.099 (2) | 0.0401 (13) | 0.0682 (17) | −0.0027 (14) | 0.0094 (16) | −0.0016 (12) |
C11 | 0.0859 (19) | 0.0550 (15) | 0.0579 (14) | 0.0203 (13) | −0.0073 (13) | −0.0015 (11) |
C12 | 0.0560 (13) | 0.0474 (12) | 0.0562 (13) | 0.0057 (10) | −0.0110 (10) | −0.0070 (10) |
C13 | 0.0585 (15) | 0.101 (2) | 0.090 (2) | −0.0091 (14) | −0.0240 (14) | −0.0389 (17) |
C14 | 0.136 (3) | 0.085 (2) | 0.100 (3) | 0.050 (2) | −0.041 (2) | 0.0008 (19) |
N1 | 0.0415 (9) | 0.0426 (9) | 0.0433 (9) | −0.0010 (7) | −0.0078 (7) | 0.0007 (7) |
N2 | 0.0507 (11) | 0.0670 (13) | 0.0716 (14) | −0.0038 (9) | −0.0350 (11) | 0.0086 (10) |
O1 | 0.0400 (7) | 0.0664 (10) | 0.0586 (9) | 0.0051 (7) | −0.0254 (7) | −0.0112 (7) |
O2 | 0.0451 (8) | 0.0412 (8) | 0.0708 (10) | −0.0064 (6) | −0.0158 (7) | −0.0025 (7) |
O3 | 0.0671 (11) | 0.1086 (16) | 0.0516 (10) | −0.0154 (10) | −0.0196 (9) | 0.0114 (10) |
O4 | 0.1010 (17) | 0.0670 (13) | 0.147 (2) | 0.0127 (12) | −0.0545 (16) | 0.0241 (13) |
S1 | 0.0304 (2) | 0.0421 (3) | 0.0500 (3) | −0.00165 (17) | −0.01472 (19) | −0.0047 (2) |
C1—C6 | 1.383 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.389 (3) | C10—C11 | 1.380 (4) |
C1—S1 | 1.7764 (18) | C10—H10 | 0.9300 |
C2—C3 | 1.384 (3) | C11—C12 | 1.392 (3) |
C2—N2 | 1.470 (3) | C11—C14 | 1.512 (4) |
C3—C4 | 1.371 (4) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—H13A | 0.9600 |
C4—C5 | 1.369 (4) | C13—H13B | 0.9600 |
C4—H4 | 0.9300 | C13—H13C | 0.9600 |
C5—C6 | 1.383 (3) | C14—H14A | 0.9600 |
C5—H5 | 0.9300 | C14—H14B | 0.9600 |
C6—H6 | 0.9300 | C14—H14C | 0.9600 |
C7—C12 | 1.382 (3) | N1—S1 | 1.6049 (18) |
C7—C8 | 1.397 (3) | N1—H1N | 0.823 (16) |
C7—N1 | 1.431 (3) | N2—O4 | 1.213 (3) |
C8—C9 | 1.393 (4) | N2—O3 | 1.218 (3) |
C8—C13 | 1.500 (4) | O1—S1 | 1.4242 (15) |
C9—C10 | 1.367 (5) | O2—S1 | 1.4295 (15) |
C6—C1—C2 | 118.12 (18) | C10—C11—C12 | 116.9 (3) |
C6—C1—S1 | 117.31 (15) | C10—C11—C14 | 122.5 (3) |
C2—C1—S1 | 124.57 (15) | C12—C11—C14 | 120.6 (3) |
C3—C2—C1 | 121.6 (2) | C7—C12—C11 | 121.1 (2) |
C3—C2—N2 | 116.78 (18) | C7—C12—H12 | 119.4 |
C1—C2—N2 | 121.63 (18) | C11—C12—H12 | 119.4 |
C4—C3—C2 | 119.0 (2) | C8—C13—H13A | 109.5 |
C4—C3—H3 | 120.5 | C8—C13—H13B | 109.5 |
C2—C3—H3 | 120.5 | H13A—C13—H13B | 109.5 |
C5—C4—C3 | 120.4 (2) | C8—C13—H13C | 109.5 |
C5—C4—H4 | 119.8 | H13A—C13—H13C | 109.5 |
C3—C4—H4 | 119.8 | H13B—C13—H13C | 109.5 |
C4—C5—C6 | 120.5 (2) | C11—C14—H14A | 109.5 |
C4—C5—H5 | 119.7 | C11—C14—H14B | 109.5 |
C6—C5—H5 | 119.7 | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 120.3 (2) | C11—C14—H14C | 109.5 |
C5—C6—H6 | 119.9 | H14A—C14—H14C | 109.5 |
C1—C6—H6 | 119.9 | H14B—C14—H14C | 109.5 |
C12—C7—C8 | 121.8 (2) | C7—N1—S1 | 121.88 (14) |
C12—C7—N1 | 117.78 (19) | C7—N1—H1N | 119.0 (17) |
C8—C7—N1 | 120.4 (2) | S1—N1—H1N | 115.8 (17) |
C9—C8—C7 | 116.1 (2) | O4—N2—O3 | 125.3 (2) |
C9—C8—C13 | 121.2 (2) | O4—N2—C2 | 117.4 (2) |
C7—C8—C13 | 122.6 (2) | O3—N2—C2 | 117.3 (2) |
C10—C9—C8 | 121.9 (3) | O1—S1—O2 | 119.85 (9) |
C10—C9—H9 | 119.1 | O1—S1—N1 | 108.74 (9) |
C8—C9—H9 | 119.1 | O2—S1—N1 | 107.05 (9) |
C9—C10—C11 | 122.1 (2) | O1—S1—C1 | 105.37 (9) |
C9—C10—H10 | 118.9 | O2—S1—C1 | 108.28 (9) |
C11—C10—H10 | 118.9 | N1—S1—C1 | 106.93 (9) |
C6—C1—C2—C3 | −0.9 (3) | C8—C7—C12—C11 | 1.7 (3) |
S1—C1—C2—C3 | 178.74 (16) | N1—C7—C12—C11 | −179.5 (2) |
C6—C1—C2—N2 | 177.9 (2) | C10—C11—C12—C7 | −2.4 (4) |
S1—C1—C2—N2 | −2.5 (3) | C14—C11—C12—C7 | 178.3 (2) |
C1—C2—C3—C4 | 2.1 (3) | C12—C7—N1—S1 | 75.0 (2) |
N2—C2—C3—C4 | −176.8 (2) | C8—C7—N1—S1 | −106.1 (2) |
C2—C3—C4—C5 | −1.2 (4) | C3—C2—N2—O4 | −59.0 (3) |
C3—C4—C5—C6 | −0.8 (4) | C1—C2—N2—O4 | 122.2 (2) |
C4—C5—C6—C1 | 2.0 (4) | C3—C2—N2—O3 | 118.6 (2) |
C2—C1—C6—C5 | −1.2 (3) | C1—C2—N2—O3 | −60.2 (3) |
S1—C1—C6—C5 | 179.19 (19) | C7—N1—S1—O1 | −41.91 (18) |
C12—C7—C8—C9 | 0.5 (3) | C7—N1—S1—O2 | −172.73 (15) |
N1—C7—C8—C9 | −178.28 (19) | C7—N1—S1—C1 | 71.41 (18) |
C12—C7—C8—C13 | 179.7 (2) | C6—C1—S1—O1 | 22.19 (19) |
N1—C7—C8—C13 | 0.9 (3) | C2—C1—S1—O1 | −157.44 (17) |
C7—C8—C9—C10 | −2.0 (4) | C6—C1—S1—O2 | 151.56 (17) |
C13—C8—C9—C10 | 178.8 (2) | C2—C1—S1—O2 | −28.1 (2) |
C8—C9—C10—C11 | 1.3 (4) | C6—C1—S1—N1 | −93.39 (18) |
C9—C10—C11—C12 | 0.9 (4) | C2—C1—S1—N1 | 86.97 (18) |
C9—C10—C11—C14 | −179.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.82 (2) | 2.27 (2) | 3.023 (2) | 152 (2) |
Symmetry code: (i) −x, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O4S |
Mr | 306.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.1987 (7), 9.6729 (9), 9.9328 (9) |
α, β, γ (°) | 84.386 (9), 72.096 (8), 89.239 (9) |
V (Å3) | 745.86 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.36 × 0.24 × 0.16 |
Data collection | |
Diffractometer | Oxford Diffraction Xcaliburdiffractometer with Sapphire CCD |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.921, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4954, 3027, 2629 |
Rint | 0.011 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.108, 1.14 |
No. of reflections | 3027 |
No. of parameters | 193 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.29 |
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 | 0.823 (16) | 2.273 (18) | 3.023 (2) | 152 (2) |
Symmetry code: (i) −x, −y, −z+2. |
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.
References
Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68, o3188. CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K. & D'Souza, J. D. (2002). Z. Naturforsch. Teil A, 57, 967–973. CAS Google Scholar
Gowda, B. T. & Shetty, M. (2004). J. Phys. Org. Chem. 17, 848–864. Web of Science CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63–72. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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-chloroarylsulfonamides (Gowda & Shetty, 2004; Shetty & Gowda, 2004), in the present work, the crystal structure of N-(2,5-dimethylphenyl)-2-nitrobenzene- sulfonamide (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 anti to the ortho-methyl and syn to the meta-methyl groups in the anilino ring, compared to the anti conformation observed between the N—H bond and both the ortho- and meta-methyl groups in the anilino ring observed in N-(2,3-dimethylphenyl)-2-nitrobenzene- sulfonamide (II) (Chaithanya et al., 2012).
The molecules in (I) are twisted at the S—N bond with the torsional angle of 71.41 (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 rings is 51.07 (8)°, compared to the values of 53.67 (8) and 56.99 (9)° in the two molecules of (II).
The amide H-atom showed the intermolecular H-bonding with the sulfonyl oxygen atom of the other molecule, generating inversion dimers (Table 1, Fig. 2.)
In the crystal structure, N1—H1N···O2(S) intermolecular hydrogen bonds link the molecules into inversion dimers (Table 1, Fig. 2.)