organic compounds
N-(3-Chlorobenzoyl)-2-methylbenzenesulfonamide
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, C14H12ClNO3S, the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. Further, the C=O bond and the meta-Cl atom in the benzoyl ring are also anti to each other. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.
Related literature
For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2004), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010) and on N-chloroarylamides, see: Gowda et al. (1996).
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/S1600536811050574/bt5728sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050574/bt5728Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811050574/bt5728Isup3.cml
The title compound was prepared by refluxing a mixture of 3-chlorobenzoic acid (0.02 mole), 2-methylbenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(3-chlorobenzoyl)2-methylbenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.
Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.
The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model with C—H distances of 0.93Å (C-aromatic) and 0.96Å (C-methyl).
All H atoms were refined with isotropic displacement parameters were set at 1.2 Ueq(C-aromatic, N) and 1.5 Ueq(C-methyl).
Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2010) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the
of N-(3-Chlorobenzoyl)- 2-methylbenzenesulfonamide (I) has been determined (Fig.1).The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II)(Suchetan et al., 2010). Further, the conformation between the C=O bond and the meta-Cl in the benzoyl ring is also anti to each other.
The molecules are twisted at the S atom with the torsional angle of 66.9 (2)°, compared to the value of 68.8 (4)° in (II).
The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 82.4 (1)°, compared to the value of 84.8 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°, compared to the value of 73.9 (1)° in (II).
The packing of molecules linked by of N—H···O(S) hydrogen bonds(Table 1) is shown in Fig. 2.
For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2004), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010) and on N-chloroarylamides, see: Gowda et al. (1996).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (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).C14H12ClNO3S | F(000) = 1280 |
Mr = 309.76 | Dx = 1.385 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3176 reflections |
a = 18.043 (2) Å | θ = 2.8–27.8° |
b = 12.046 (1) Å | µ = 0.40 mm−1 |
c = 15.596 (2) Å | T = 293 K |
β = 118.77 (2)° | Prism, colourless |
V = 2971.3 (6) Å3 | 0.40 × 0.36 × 0.32 mm |
Z = 8 |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 3024 independent reflections |
Radiation source: fine-focus sealed tube | 2463 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Rotation method data acquisition using ω and phi scans. | θmax = 26.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −22→18 |
Tmin = 0.856, Tmax = 0.882 | k = −15→11 |
5996 measured reflections | l = −18→19 |
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) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0488P)2 + 4.0385P] where P = (Fo2 + 2Fc2)/3 |
3024 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.45 e Å−3 |
1 restraint | Δρmin = −0.64 e Å−3 |
C14H12ClNO3S | V = 2971.3 (6) Å3 |
Mr = 309.76 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.043 (2) Å | µ = 0.40 mm−1 |
b = 12.046 (1) Å | T = 293 K |
c = 15.596 (2) Å | 0.40 × 0.36 × 0.32 mm |
β = 118.77 (2)° |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 3024 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2463 reflections with I > 2σ(I) |
Tmin = 0.856, Tmax = 0.882 | Rint = 0.012 |
5996 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.45 e Å−3 |
3024 reflections | Δρmin = −0.64 e Å−3 |
185 parameters |
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 | 0.34287 (11) | 0.11403 (15) | 0.87322 (14) | 0.0349 (4) | |
C2 | 0.29479 (13) | 0.18523 (18) | 0.79536 (16) | 0.0449 (5) | |
C3 | 0.30275 (17) | 0.1707 (2) | 0.71180 (18) | 0.0604 (6) | |
H3 | 0.2716 | 0.2161 | 0.6580 | 0.072* | |
C4 | 0.35502 (18) | 0.0918 (2) | 0.70565 (19) | 0.0627 (7) | |
H4 | 0.3591 | 0.0854 | 0.6486 | 0.075* | |
C5 | 0.40121 (16) | 0.0224 (2) | 0.78294 (19) | 0.0546 (6) | |
H5 | 0.4363 | −0.0312 | 0.7785 | 0.065* | |
C6 | 0.39508 (13) | 0.03297 (18) | 0.86754 (16) | 0.0434 (5) | |
H6 | 0.4257 | −0.0139 | 0.9203 | 0.052* | |
C7 | 0.22402 (13) | −0.03082 (17) | 0.94079 (16) | 0.0418 (5) | |
C8 | 0.13770 (14) | −0.06030 (18) | 0.92343 (16) | 0.0451 (5) | |
C9 | 0.07257 (14) | 0.0159 (2) | 0.89365 (18) | 0.0535 (6) | |
H9 | 0.0814 | 0.0905 | 0.8859 | 0.064* | |
C10 | −0.00629 (16) | −0.0220 (3) | 0.8757 (2) | 0.0736 (8) | |
C11 | −0.0197 (2) | −0.1309 (3) | 0.8889 (3) | 0.0970 (12) | |
H11 | −0.0729 | −0.1545 | 0.8770 | 0.116* | |
C12 | 0.0461 (2) | −0.2054 (3) | 0.9201 (3) | 0.0981 (12) | |
H12 | 0.0372 | −0.2793 | 0.9298 | 0.118* | |
C13 | 0.12381 (17) | −0.1717 (2) | 0.9368 (2) | 0.0633 (7) | |
H13 | 0.1678 | −0.2227 | 0.9571 | 0.076* | |
C14 | 0.23804 (18) | 0.2758 (2) | 0.7967 (2) | 0.0657 (7) | |
H14A | 0.2719 | 0.3353 | 0.8380 | 0.079* | |
H14B | 0.2025 | 0.2469 | 0.8214 | 0.079* | |
H14C | 0.2036 | 0.3032 | 0.7314 | 0.079* | |
N1 | 0.24872 (11) | 0.07910 (15) | 0.96409 (14) | 0.0425 (4) | |
H1N | 0.2195 (14) | 0.1279 (17) | 0.9688 (18) | 0.051* | |
O1 | 0.40644 (10) | 0.05491 (15) | 1.05526 (11) | 0.0546 (4) | |
O2 | 0.34229 (10) | 0.23938 (13) | 1.01017 (13) | 0.0547 (4) | |
O3 | 0.27146 (10) | −0.09871 (13) | 0.93618 (14) | 0.0578 (4) | |
Cl1 | −0.08922 (5) | 0.07097 (11) | 0.83538 (9) | 0.1187 (4) | |
S1 | 0.34256 (3) | 0.12455 (4) | 0.98556 (4) | 0.03864 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0307 (9) | 0.0335 (10) | 0.0424 (10) | −0.0031 (8) | 0.0192 (8) | −0.0026 (8) |
C2 | 0.0401 (11) | 0.0408 (11) | 0.0523 (12) | 0.0002 (9) | 0.0210 (10) | 0.0047 (10) |
C3 | 0.0678 (16) | 0.0615 (15) | 0.0487 (13) | 0.0021 (13) | 0.0255 (12) | 0.0117 (12) |
C4 | 0.0773 (18) | 0.0704 (17) | 0.0510 (14) | −0.0068 (14) | 0.0393 (13) | −0.0077 (13) |
C5 | 0.0567 (14) | 0.0533 (14) | 0.0659 (15) | 0.0006 (11) | 0.0393 (12) | −0.0115 (12) |
C6 | 0.0397 (11) | 0.0412 (11) | 0.0517 (12) | 0.0025 (9) | 0.0239 (9) | −0.0007 (9) |
C7 | 0.0449 (11) | 0.0368 (11) | 0.0473 (11) | −0.0006 (9) | 0.0251 (10) | −0.0003 (9) |
C8 | 0.0448 (12) | 0.0423 (12) | 0.0512 (12) | −0.0074 (9) | 0.0254 (10) | −0.0072 (10) |
C9 | 0.0428 (12) | 0.0514 (13) | 0.0631 (14) | −0.0037 (10) | 0.0229 (11) | −0.0074 (11) |
C10 | 0.0432 (14) | 0.092 (2) | 0.0811 (19) | −0.0048 (14) | 0.0263 (13) | −0.0196 (17) |
C11 | 0.0587 (18) | 0.090 (2) | 0.149 (3) | −0.0355 (18) | 0.055 (2) | −0.034 (2) |
C12 | 0.093 (3) | 0.0636 (19) | 0.155 (4) | −0.0324 (19) | 0.073 (3) | −0.015 (2) |
C13 | 0.0608 (15) | 0.0442 (13) | 0.092 (2) | −0.0093 (12) | 0.0422 (15) | −0.0075 (13) |
C14 | 0.0622 (16) | 0.0524 (14) | 0.0783 (18) | 0.0205 (13) | 0.0304 (14) | 0.0163 (13) |
N1 | 0.0388 (9) | 0.0374 (9) | 0.0605 (11) | −0.0007 (7) | 0.0312 (9) | −0.0054 (8) |
O1 | 0.0428 (8) | 0.0729 (11) | 0.0445 (8) | 0.0079 (8) | 0.0182 (7) | 0.0070 (8) |
O2 | 0.0522 (9) | 0.0466 (9) | 0.0766 (11) | −0.0129 (7) | 0.0401 (9) | −0.0226 (8) |
O3 | 0.0557 (10) | 0.0395 (8) | 0.0884 (13) | 0.0041 (7) | 0.0428 (9) | −0.0047 (8) |
Cl1 | 0.0500 (4) | 0.1486 (10) | 0.1396 (9) | 0.0240 (5) | 0.0313 (5) | −0.0175 (7) |
S1 | 0.0337 (3) | 0.0404 (3) | 0.0455 (3) | −0.0024 (2) | 0.0219 (2) | −0.0056 (2) |
C1—C6 | 1.389 (3) | C9—C10 | 1.388 (3) |
C1—C2 | 1.396 (3) | C9—H9 | 0.9300 |
C1—S1 | 1.759 (2) | C10—C11 | 1.368 (5) |
C2—C3 | 1.389 (3) | C10—Cl1 | 1.727 (3) |
C2—C14 | 1.503 (3) | C11—C12 | 1.376 (5) |
C3—C4 | 1.375 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.359 (4) |
C4—C5 | 1.370 (4) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.382 (3) | C14—H14A | 0.9600 |
C5—H5 | 0.9300 | C14—H14B | 0.9600 |
C6—H6 | 0.9300 | C14—H14C | 0.9600 |
C7—O3 | 1.211 (2) | N1—S1 | 1.6532 (17) |
C7—N1 | 1.389 (3) | N1—H1N | 0.816 (16) |
C7—C8 | 1.490 (3) | O1—S1 | 1.4170 (17) |
C8—C9 | 1.384 (3) | O2—S1 | 1.4361 (16) |
C8—C13 | 1.399 (3) | ||
C6—C1—C2 | 122.21 (19) | C11—C10—C9 | 121.5 (3) |
C6—C1—S1 | 116.20 (16) | C11—C10—Cl1 | 119.5 (2) |
C2—C1—S1 | 121.57 (15) | C9—C10—Cl1 | 119.0 (3) |
C3—C2—C1 | 115.9 (2) | C10—C11—C12 | 119.6 (3) |
C3—C2—C14 | 118.8 (2) | C10—C11—H11 | 120.2 |
C1—C2—C14 | 125.2 (2) | C12—C11—H11 | 120.2 |
C4—C3—C2 | 122.4 (2) | C13—C12—C11 | 120.5 (3) |
C4—C3—H3 | 118.8 | C13—C12—H12 | 119.7 |
C2—C3—H3 | 118.8 | C11—C12—H12 | 119.7 |
C5—C4—C3 | 120.5 (2) | C12—C13—C8 | 120.0 (3) |
C5—C4—H4 | 119.8 | C12—C13—H13 | 120.0 |
C3—C4—H4 | 119.8 | C8—C13—H13 | 120.0 |
C4—C5—C6 | 119.3 (2) | C2—C14—H14A | 109.5 |
C4—C5—H5 | 120.3 | C2—C14—H14B | 109.5 |
C6—C5—H5 | 120.3 | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 119.6 (2) | C2—C14—H14C | 109.5 |
C5—C6—H6 | 120.2 | H14A—C14—H14C | 109.5 |
C1—C6—H6 | 120.2 | H14B—C14—H14C | 109.5 |
O3—C7—N1 | 120.84 (19) | C7—N1—S1 | 122.50 (14) |
O3—C7—C8 | 122.37 (19) | C7—N1—H1N | 124.8 (18) |
N1—C7—C8 | 116.78 (18) | S1—N1—H1N | 112.7 (18) |
C9—C8—C13 | 120.2 (2) | O1—S1—O2 | 118.13 (11) |
C9—C8—C7 | 123.2 (2) | O1—S1—N1 | 109.57 (10) |
C13—C8—C7 | 116.6 (2) | O2—S1—N1 | 103.78 (9) |
C8—C9—C10 | 118.1 (2) | O1—S1—C1 | 109.27 (9) |
C8—C9—H9 | 120.9 | O2—S1—C1 | 109.73 (10) |
C10—C9—H9 | 120.9 | N1—S1—C1 | 105.56 (9) |
C6—C1—C2—C3 | −0.5 (3) | C8—C9—C10—Cl1 | −178.3 (2) |
S1—C1—C2—C3 | 177.92 (17) | C9—C10—C11—C12 | −0.6 (6) |
C6—C1—C2—C14 | −179.0 (2) | Cl1—C10—C11—C12 | 179.4 (3) |
S1—C1—C2—C14 | −0.6 (3) | C10—C11—C12—C13 | −0.6 (6) |
C1—C2—C3—C4 | −0.4 (4) | C11—C12—C13—C8 | 0.7 (6) |
C14—C2—C3—C4 | 178.2 (3) | C9—C8—C13—C12 | 0.3 (4) |
C2—C3—C4—C5 | 0.8 (4) | C7—C8—C13—C12 | −178.5 (3) |
C3—C4—C5—C6 | −0.3 (4) | O3—C7—N1—S1 | 0.7 (3) |
C4—C5—C6—C1 | −0.5 (3) | C8—C7—N1—S1 | 179.90 (15) |
C2—C1—C6—C5 | 0.9 (3) | C7—N1—S1—O1 | −50.7 (2) |
S1—C1—C6—C5 | −177.54 (17) | C7—N1—S1—O2 | −177.71 (18) |
O3—C7—C8—C9 | −156.0 (2) | C7—N1—S1—C1 | 66.88 (19) |
N1—C7—C8—C9 | 24.8 (3) | C6—C1—S1—O1 | 7.75 (19) |
O3—C7—C8—C13 | 22.7 (3) | C2—C1—S1—O1 | −170.73 (16) |
N1—C7—C8—C13 | −156.5 (2) | C6—C1—S1—O2 | 138.74 (16) |
C13—C8—C9—C10 | −1.4 (4) | C2—C1—S1—O2 | −39.75 (19) |
C7—C8—C9—C10 | 177.3 (2) | C6—C1—S1—N1 | −110.00 (16) |
C8—C9—C10—C11 | 1.6 (4) | C2—C1—S1—N1 | 71.51 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.82 (2) | 2.06 (2) | 2.876 (2) | 174 (2) |
Symmetry code: (i) −x+1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClNO3S |
Mr | 309.76 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 18.043 (2), 12.046 (1), 15.596 (2) |
β (°) | 118.77 (2) |
V (Å3) | 2971.3 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.40 × 0.36 × 0.32 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.856, 0.882 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5996, 3024, 2463 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.113, 1.03 |
No. of reflections | 3024 |
No. of parameters | 185 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.64 |
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 | 0.816 (16) | 2.063 (17) | 2.876 (2) | 174 (2) |
Symmetry code: (i) −x+1/2, −y+1/2, −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 the faculty.
References
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Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1024. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2004), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2010) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(3-Chlorobenzoyl)- 2-methylbenzenesulfonamide (I) has been determined (Fig.1).
The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II)(Suchetan et al., 2010). Further, the conformation between the C=O bond and the meta-Cl in the benzoyl ring is also anti to each other.
The molecules are twisted at the S atom with the torsional angle of 66.9 (2)°, compared to the value of 68.8 (4)° in (II).
The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 82.4 (1)°, compared to the value of 84.8 (1)° in (II). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°, compared to the value of 73.9 (1)° in (II).
The packing of molecules linked by of N—H···O(S) hydrogen bonds(Table 1) is shown in Fig. 2.