organic compounds
2-Chloro-N-(3-methylbenzoyl)benzenesulfonamide
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 is in an antiperiplanar conformation to the C=O bond. The dihedral angle between the two aromatic rings is 74.7 (1)°. The features inversion-related dimers linked by N—H⋯O hydrogen bonds.
Related literature
For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl and for related structures, see: Gowda et al. (2009, 2010); Suchetan et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; 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/S1600536810016235/bt5261sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016235/bt5261Isup2.hkl
The title compound was prepared by refluxing a mixture of 3-methylbenzoic acid, 2-chlorobenzenesulfonamide and phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into ice cold water. The solid 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 refined with a distance restraint of N—H = 0.86 (2)Å. The other H atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.
As a part of studying the effect of ring and the side chain substitutions on the crystal structures of N-aryl
(Gowda et al., 2009, 2010; Suchetan et al., 2010)), in the present work, the structure of 2-chloro-N-(3-methylbenzoyl)benzenesulfonamide, (I), has been determined. In the C—SO2—NH—C(O) segment, the N—H bond is anti to the C=O bond (Fig.1), similar to those observed in 2-chloro-N-(2-methylbenzoyl)benzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010).Further, the conformation of the C=O bond in the C—SO2—NH—C(O) segment of (I) is anti to the meta-methyl group in the benzoyl ring, contrary to the syn conformation observed between the ortho-methyl group and the C=O bond in (II).
The molecules are twisted at the S atom with the torsional angle of -66.5 (2)°, compared to those of -64.0 (2)° in (II), -66.9 (3)° in (III), and 66.7 (2)° in (IV).
The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.4 (1)°, compared to the values of 84.8 (1)° in (II), 86.5 (1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 74.7 (1)°, compared to the values of 78.7 (1)° in (II), of 80.3 (1) in (III) and 73.3 (1)° in (IV).
The packing of molecules linked by N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.
For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl
and for related structures, see: Gowda et al. (2009, 2010); Suchetan et al. (2010).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 = 1.407 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5313 reflections |
a = 12.4487 (8) Å | θ = 2.8–27.7° |
b = 13.4619 (8) Å | µ = 0.41 mm−1 |
c = 17.455 (1) Å | T = 299 K |
V = 2925.2 (3) Å3 | Prism, colourless |
Z = 8 | 0.30 × 0.30 × 0.20 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2955 independent reflections |
Radiation source: fine-focus sealed tube | 2422 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
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 = −15→11 |
Tmin = 0.887, Tmax = 0.923 | k = −16→9 |
7216 measured reflections | l = −12→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0429P)2 + 1.518P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2955 reflections | Δρmax = 0.20 e Å−3 |
186 parameters | Δρmin = −0.28 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0265 (11) |
C14H12ClNO3S | V = 2925.2 (3) Å3 |
Mr = 309.76 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.4487 (8) Å | µ = 0.41 mm−1 |
b = 13.4619 (8) Å | T = 299 K |
c = 17.455 (1) Å | 0.30 × 0.30 × 0.20 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2955 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2422 reflections with I > 2σ(I) |
Tmin = 0.887, Tmax = 0.923 | Rint = 0.014 |
7216 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.20 e Å−3 |
2955 reflections | Δρmin = −0.28 e Å−3 |
186 parameters |
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | −0.00620 (14) | 0.25666 (13) | 0.42487 (10) | 0.0366 (4) | |
C2 | −0.09360 (15) | 0.24307 (16) | 0.47300 (11) | 0.0452 (5) | |
C3 | −0.1408 (2) | 0.15010 (19) | 0.47939 (15) | 0.0634 (6) | |
H3 | −0.1992 | 0.1408 | 0.5118 | 0.076* | |
C4 | −0.1008 (2) | 0.07177 (18) | 0.43768 (16) | 0.0688 (7) | |
H4 | −0.1323 | 0.0095 | 0.4423 | 0.083* | |
C5 | −0.0152 (2) | 0.08419 (16) | 0.38944 (15) | 0.0627 (6) | |
H5 | 0.0109 | 0.0307 | 0.3614 | 0.075* | |
C6 | 0.03249 (18) | 0.17676 (14) | 0.38256 (12) | 0.0482 (5) | |
H6 | 0.0904 | 0.1855 | 0.3496 | 0.058* | |
C7 | −0.06413 (15) | 0.45303 (13) | 0.31212 (10) | 0.0381 (4) | |
C8 | −0.13360 (15) | 0.53961 (13) | 0.29432 (10) | 0.0373 (4) | |
C9 | −0.11657 (16) | 0.63233 (13) | 0.32775 (11) | 0.0404 (4) | |
H9 | −0.0593 | 0.6410 | 0.3613 | 0.049* | |
C10 | −0.18376 (18) | 0.71203 (15) | 0.31173 (11) | 0.0476 (5) | |
C11 | −0.26884 (18) | 0.69666 (18) | 0.26178 (13) | 0.0581 (6) | |
H11 | −0.3156 | 0.7487 | 0.2510 | 0.070* | |
C12 | −0.28515 (18) | 0.60527 (19) | 0.22792 (13) | 0.0598 (6) | |
H12 | −0.3426 | 0.5966 | 0.1946 | 0.072* | |
C13 | −0.21746 (16) | 0.52658 (15) | 0.24283 (11) | 0.0484 (5) | |
H13 | −0.2278 | 0.4657 | 0.2188 | 0.058* | |
C14 | −0.1632 (2) | 0.81144 (17) | 0.34798 (15) | 0.0693 (7) | |
H14A | −0.1193 | 0.8509 | 0.3145 | 0.083* | |
H14B | −0.1267 | 0.8023 | 0.3959 | 0.083* | |
H14C | −0.2303 | 0.8447 | 0.3567 | 0.083* | |
N1 | −0.01969 (13) | 0.45407 (11) | 0.38535 (9) | 0.0409 (4) | |
H1N | −0.0421 (17) | 0.4933 (14) | 0.4174 (11) | 0.049* | |
O1 | 0.14949 (11) | 0.35731 (10) | 0.36476 (9) | 0.0497 (4) | |
O2 | 0.08974 (11) | 0.40436 (10) | 0.49378 (8) | 0.0465 (4) | |
O3 | −0.04744 (13) | 0.38456 (10) | 0.26879 (8) | 0.0528 (4) | |
Cl1 | −0.14827 (5) | 0.34034 (5) | 0.52560 (4) | 0.0706 (2) | |
S1 | 0.06458 (4) | 0.37028 (3) | 0.41809 (3) | 0.03622 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0387 (9) | 0.0376 (9) | 0.0335 (9) | 0.0023 (8) | 0.0006 (7) | 0.0023 (7) |
C2 | 0.0403 (10) | 0.0532 (11) | 0.0422 (10) | −0.0003 (9) | 0.0050 (8) | −0.0039 (9) |
C3 | 0.0539 (13) | 0.0707 (15) | 0.0656 (15) | −0.0153 (12) | 0.0158 (12) | 0.0052 (12) |
C4 | 0.0806 (17) | 0.0468 (12) | 0.0789 (17) | −0.0165 (12) | 0.0058 (14) | 0.0043 (12) |
C5 | 0.0829 (17) | 0.0386 (11) | 0.0665 (15) | 0.0010 (11) | 0.0102 (13) | −0.0030 (10) |
C6 | 0.0581 (12) | 0.0400 (10) | 0.0464 (11) | 0.0047 (9) | 0.0100 (10) | 0.0002 (9) |
C7 | 0.0421 (10) | 0.0362 (9) | 0.0362 (9) | −0.0064 (8) | −0.0011 (8) | 0.0008 (7) |
C8 | 0.0403 (10) | 0.0395 (9) | 0.0321 (9) | −0.0028 (8) | −0.0009 (7) | 0.0073 (7) |
C9 | 0.0469 (10) | 0.0395 (9) | 0.0350 (9) | −0.0003 (8) | 0.0001 (8) | 0.0052 (7) |
C10 | 0.0554 (12) | 0.0446 (10) | 0.0428 (10) | 0.0075 (9) | 0.0127 (9) | 0.0098 (9) |
C11 | 0.0504 (13) | 0.0652 (13) | 0.0587 (13) | 0.0154 (11) | 0.0049 (10) | 0.0234 (11) |
C12 | 0.0463 (12) | 0.0789 (16) | 0.0540 (13) | −0.0044 (11) | −0.0136 (10) | 0.0220 (12) |
C13 | 0.0500 (11) | 0.0536 (11) | 0.0417 (10) | −0.0112 (9) | −0.0079 (9) | 0.0090 (9) |
C14 | 0.0911 (18) | 0.0452 (12) | 0.0716 (16) | 0.0147 (12) | 0.0123 (14) | 0.0024 (11) |
N1 | 0.0514 (9) | 0.0365 (8) | 0.0349 (8) | 0.0099 (7) | −0.0053 (7) | −0.0028 (6) |
O1 | 0.0420 (7) | 0.0497 (8) | 0.0576 (9) | −0.0001 (6) | 0.0114 (7) | 0.0031 (7) |
O2 | 0.0493 (8) | 0.0466 (7) | 0.0438 (8) | 0.0065 (6) | −0.0130 (6) | −0.0061 (6) |
O3 | 0.0656 (10) | 0.0463 (8) | 0.0464 (8) | 0.0020 (7) | −0.0051 (7) | −0.0112 (6) |
Cl1 | 0.0563 (4) | 0.0847 (4) | 0.0708 (4) | 0.0028 (3) | 0.0242 (3) | −0.0256 (3) |
S1 | 0.0360 (2) | 0.0358 (2) | 0.0368 (3) | 0.00304 (18) | −0.00100 (18) | −0.00045 (18) |
C1—C2 | 1.387 (3) | C9—C10 | 1.389 (3) |
C1—C6 | 1.391 (3) | C9—H9 | 0.9300 |
C1—S1 | 1.7691 (18) | C10—C11 | 1.387 (3) |
C2—C3 | 1.387 (3) | C10—C14 | 1.502 (3) |
C2—Cl1 | 1.738 (2) | C11—C12 | 1.380 (3) |
C3—C4 | 1.375 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.378 (3) |
C4—C5 | 1.368 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.385 (3) | C14—H14A | 0.9600 |
C5—H5 | 0.9300 | C14—H14B | 0.9600 |
C6—H6 | 0.9300 | C14—H14C | 0.9600 |
C7—O3 | 1.210 (2) | N1—S1 | 1.6430 (16) |
C7—N1 | 1.393 (2) | N1—H1N | 0.819 (15) |
C7—C8 | 1.484 (3) | O1—S1 | 1.4192 (14) |
C8—C13 | 1.389 (3) | O2—S1 | 1.4333 (14) |
C8—C9 | 1.394 (3) | ||
C2—C1—C6 | 119.43 (18) | C11—C10—C9 | 118.1 (2) |
C2—C1—S1 | 123.05 (14) | C11—C10—C14 | 121.9 (2) |
C6—C1—S1 | 117.43 (14) | C9—C10—C14 | 120.0 (2) |
C1—C2—C3 | 119.99 (19) | C12—C11—C10 | 121.0 (2) |
C1—C2—Cl1 | 121.86 (16) | C12—C11—H11 | 119.5 |
C3—C2—Cl1 | 118.14 (16) | C10—C11—H11 | 119.5 |
C4—C3—C2 | 119.8 (2) | C13—C12—C11 | 121.0 (2) |
C4—C3—H3 | 120.1 | C13—C12—H12 | 119.5 |
C2—C3—H3 | 120.1 | C11—C12—H12 | 119.5 |
C5—C4—C3 | 120.9 (2) | C12—C13—C8 | 119.0 (2) |
C5—C4—H4 | 119.5 | C12—C13—H13 | 120.5 |
C3—C4—H4 | 119.5 | C8—C13—H13 | 120.5 |
C4—C5—C6 | 119.8 (2) | C10—C14—H14A | 109.5 |
C4—C5—H5 | 120.1 | C10—C14—H14B | 109.5 |
C6—C5—H5 | 120.1 | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 120.1 (2) | C10—C14—H14C | 109.5 |
C5—C6—H6 | 120.0 | H14A—C14—H14C | 109.5 |
C1—C6—H6 | 120.0 | H14B—C14—H14C | 109.5 |
O3—C7—N1 | 120.86 (17) | C7—N1—S1 | 124.46 (13) |
O3—C7—C8 | 124.56 (17) | C7—N1—H1N | 119.9 (15) |
N1—C7—C8 | 114.55 (16) | S1—N1—H1N | 115.0 (15) |
C13—C8—C9 | 119.89 (18) | O1—S1—O2 | 118.76 (9) |
C13—C8—C7 | 118.31 (17) | O1—S1—N1 | 109.39 (9) |
C9—C8—C7 | 121.80 (16) | O2—S1—N1 | 103.91 (8) |
C10—C9—C8 | 121.05 (18) | O1—S1—C1 | 107.97 (8) |
C10—C9—H9 | 119.5 | O2—S1—C1 | 108.90 (8) |
C8—C9—H9 | 119.5 | N1—S1—C1 | 107.39 (8) |
C6—C1—C2—C3 | 0.8 (3) | C8—C9—C10—C14 | −179.49 (19) |
S1—C1—C2—C3 | −175.56 (17) | C9—C10—C11—C12 | −1.1 (3) |
C6—C1—C2—Cl1 | −178.29 (16) | C14—C10—C11—C12 | 178.7 (2) |
S1—C1—C2—Cl1 | 5.3 (2) | C10—C11—C12—C13 | 0.1 (3) |
C1—C2—C3—C4 | −0.2 (4) | C11—C12—C13—C8 | 1.7 (3) |
Cl1—C2—C3—C4 | 178.9 (2) | C9—C8—C13—C12 | −2.5 (3) |
C2—C3—C4—C5 | −0.3 (4) | C7—C8—C13—C12 | 177.57 (18) |
C3—C4—C5—C6 | 0.3 (4) | O3—C7—N1—S1 | 4.7 (3) |
C4—C5—C6—C1 | 0.4 (4) | C8—C7—N1—S1 | −176.87 (13) |
C2—C1—C6—C5 | −0.9 (3) | C7—N1—S1—O1 | 50.47 (18) |
S1—C1—C6—C5 | 175.69 (18) | C7—N1—S1—O2 | 178.25 (15) |
O3—C7—C8—C13 | 27.9 (3) | C7—N1—S1—C1 | −66.46 (17) |
N1—C7—C8—C13 | −150.47 (17) | C2—C1—S1—O1 | 179.10 (16) |
O3—C7—C8—C9 | −152.07 (19) | C6—C1—S1—O1 | 2.64 (18) |
N1—C7—C8—C9 | 29.6 (2) | C2—C1—S1—O2 | 48.88 (18) |
C13—C8—C9—C10 | 1.4 (3) | C6—C1—S1—O2 | −127.58 (15) |
C7—C8—C9—C10 | −178.59 (17) | C2—C1—S1—N1 | −63.04 (18) |
C8—C9—C10—C11 | 0.4 (3) | C6—C1—S1—N1 | 120.49 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.82 (2) | 2.16 (2) | 2.974 (2) | 176 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClNO3S |
Mr | 309.76 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 299 |
a, b, c (Å) | 12.4487 (8), 13.4619 (8), 17.455 (1) |
V (Å3) | 2925.2 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.887, 0.923 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7216, 2955, 2422 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.095, 1.04 |
No. of reflections | 2955 |
No. of parameters | 186 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.28 |
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 | 0.819 (15) | 2.156 (16) | 2.974 (2) | 176 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
Acknowledgements
PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.
References
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1281. Web of Science CSD CrossRef 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 ring and the side chain substitutions on the crystal structures of N-aryl sulfonamides (Gowda et al., 2009, 2010; Suchetan et al., 2010)), in the present work, the structure of 2-chloro-N-(3-methylbenzoyl)benzenesulfonamide, (I), has been determined. In the C—SO2—NH—C(O) segment, the N—H bond is anti to the C=O bond (Fig.1), similar to those observed in 2-chloro-N-(2-methylbenzoyl)benzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010).
Further, the conformation of the C=O bond in the C—SO2—NH—C(O) segment of (I) is anti to the meta-methyl group in the benzoyl ring, contrary to the syn conformation observed between the ortho-methyl group and the C=O bond in (II).
The molecules are twisted at the S atom with the torsional angle of -66.5 (2)°, compared to those of -64.0 (2)° in (II), -66.9 (3)° in (III), and 66.7 (2)° in (IV).
The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.4 (1)°, compared to the values of 84.8 (1)° in (II), 86.5 (1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 74.7 (1)°, compared to the values of 78.7 (1)° in (II), of 80.3 (1) in (III) and 73.3 (1)° in (IV).
The packing of molecules linked by N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.