Acta Cryst. (2012). E68, o2626 [ doi:10.1107/S1600536812033764 ]
The asymmetric unit of the title compound, C8H8ClNO3S, consists of two crystallographically independent molecules (A and B). The dihedral angles between the benzene ring and amide C-C(=O)-NH- plane are 87.6 (3) (molecule A) and 86.0 (3)° (molecule B). In the crystal, the independent molecules are alternately linked by N-H
O hydrogen bonds into an infinite chain along the b axis. Short intermolecular ClCl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed.
To a vigorously stirred mixture of 4-chlorobenzenesulphonamide and silica sulfuric acid, acid chloride or acid anhydride was added at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added and the solid catalyst was removed by filtration. The filtrate was washed with water, dried and evaporated. The crude product was purified by recrystallization from an ethanol solution to yield colourless single crystals of the title compound.
The N-bound H atoms were located in a difference Fourier map and refined freely [N1A—H1NA = 0.865 (14) Å and N1B—H1NB = 0.871 (14) Å]. The remaining H atoms were positioned geometrically (C—H = 0.95 and 0.98 Å) and refined using a riding model with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating group model was applied to the methyl group. Four outliers, (204), (100), (348) and (233), were omitted in the final refinement.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./is5173fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. |
![[Figure 2]](./is5173fig2thm.gif)
| Fig. 2. The crystal packing of the title compound viewed along the c axis. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted. |
| C8H8ClNO3S | F(000) = 960 |
| Mr = 233.66 | Dx = 1.593 Mg m−3 |
| Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yc | Cell parameters from 9840 reflections |
| a = 12.1801 (6) Å | θ = 2.5–32.6° |
| b = 9.2529 (4) Å | µ = 0.59 mm−1 |
| c = 17.6769 (8) Å | T = 100 K |
| β = 101.979 (1)° | Block, colourless |
| V = 1948.83 (16) Å3 | 0.36 × 0.14 × 0.14 mm |
| Z = 8 |
| Bruker APEX DUO CCD area-detector diffractometer | 7130 independent reflections |
| Radiation source: fine-focus sealed tube | 5439 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| φ and ω scans | θmax = 32.7°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −18→18 |
| Tmin = 0.819, Tmax = 0.923 | k = −14→13 |
| 45479 measured reflections | l = −26→26 |
| 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0436P)2 + 0.5704P] where P = (Fo2 + 2Fc2)/3 |
| 7130 reflections | (Δ/σ)max = 0.001 |
| 263 parameters | Δρmax = 0.48 e Å−3 |
| 0 restraints | Δρmin = −0.52 e Å−3 |
| C8H8ClNO3S | V = 1948.83 (16) Å3 |
| Mr = 233.66 | Z = 8 |
| Monoclinic, P2/c | Mo Kα radiation |
| a = 12.1801 (6) Å | µ = 0.59 mm−1 |
| b = 9.2529 (4) Å | T = 100 K |
| c = 17.6769 (8) Å | 0.36 × 0.14 × 0.14 mm |
| β = 101.979 (1)° |
| Bruker APEX DUO CCD area-detector diffractometer | 7130 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5439 reflections with I > 2σ(I) |
| Tmin = 0.819, Tmax = 0.923 | Rint = 0.033 |
| 45479 measured reflections | θmax = 32.7° |
| R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.090 | Δρmax = 0.48 e Å−3 |
| S = 1.04 | Δρmin = −0.52 e Å−3 |
| 7130 reflections | Absolute structure: ? |
| 263 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 | ||
| Cl1A | 0.47973 (2) | 0.51064 (3) | 0.405269 (18) | 0.02673 (7) | |
| S1A | 0.170782 (19) | 0.51977 (2) | 0.076741 (14) | 0.01367 (6) | |
| O1A | 0.19060 (6) | 0.64897 (8) | 0.03653 (4) | 0.02048 (14) | |
| O2A | 0.17384 (6) | 0.38233 (8) | 0.04030 (4) | 0.01910 (14) | |
| O3A | 0.03482 (6) | 0.33069 (7) | 0.15483 (4) | 0.01845 (14) | |
| N1A | 0.04580 (7) | 0.54746 (8) | 0.09688 (5) | 0.01463 (14) | |
| C1A | 0.29561 (8) | 0.64713 (10) | 0.20474 (6) | 0.01909 (18) | |
| H1AA | 0.2712 | 0.7362 | 0.1802 | 0.023* | |
| C2A | 0.36445 (8) | 0.64567 (11) | 0.27788 (6) | 0.02079 (19) | |
| H2AA | 0.3879 | 0.7335 | 0.3042 | 0.025* | |
| C3A | 0.39837 (8) | 0.51313 (11) | 0.31194 (6) | 0.01803 (19) | |
| C4A | 0.36704 (8) | 0.38278 (11) | 0.27505 (6) | 0.01842 (18) | |
| H4AA | 0.3926 | 0.2939 | 0.2994 | 0.022* | |
| C5A | 0.29771 (7) | 0.38417 (10) | 0.20193 (6) | 0.01646 (17) | |
| H5AA | 0.2745 | 0.2962 | 0.1757 | 0.020* | |
| C6A | 0.26276 (8) | 0.51635 (9) | 0.16772 (6) | 0.01437 (17) | |
| C7A | −0.00697 (7) | 0.44855 (9) | 0.13606 (5) | 0.01418 (16) | |
| C8A | −0.11629 (9) | 0.49932 (10) | 0.15322 (7) | 0.01856 (19) | |
| H8AA | −0.1411 | 0.4314 | 0.1888 | 0.028* | |
| H8AB | −0.1729 | 0.5044 | 0.1050 | 0.028* | |
| H8AC | −0.1062 | 0.5953 | 0.1771 | 0.028* | |
| Cl1B | 0.52074 (2) | 0.97797 (3) | −0.155284 (17) | 0.02637 (7) | |
| S1B | 0.82941 (2) | 1.00993 (2) | 0.172976 (15) | 0.01367 (6) | |
| O1B | 0.80290 (6) | 1.13770 (8) | 0.21146 (4) | 0.01954 (14) | |
| O2B | 0.83407 (6) | 0.87333 (8) | 0.21118 (4) | 0.01972 (14) | |
| O3B | 0.97057 (6) | 0.83316 (7) | 0.09436 (4) | 0.01887 (14) | |
| N1B | 0.95264 (7) | 1.04795 (8) | 0.15212 (5) | 0.01459 (14) | |
| C1B | 0.69388 (8) | 1.12533 (10) | 0.04604 (6) | 0.01691 (17) | |
| H1BA | 0.7112 | 1.2157 | 0.0712 | 0.020* | |
| C2B | 0.62534 (8) | 1.11904 (10) | −0.02700 (6) | 0.01873 (18) | |
| H2BA | 0.5950 | 1.2048 | −0.0526 | 0.022* | |
| C3B | 0.60174 (8) | 0.98501 (11) | −0.06205 (6) | 0.01785 (18) | |
| C4B | 0.64282 (8) | 0.85698 (11) | −0.02594 (6) | 0.01874 (18) | |
| H4BA | 0.6241 | 0.7667 | −0.0508 | 0.022* | |
| C5B | 0.71197 (8) | 0.86331 (10) | 0.04738 (6) | 0.01664 (17) | |
| H5BA | 0.7415 | 0.7773 | 0.0732 | 0.020* | |
| C6B | 0.73726 (8) | 0.99763 (9) | 0.08230 (6) | 0.01408 (17) | |
| C7B | 1.00893 (7) | 0.95272 (9) | 0.11338 (5) | 0.01431 (16) | |
| C8B | 1.11652 (8) | 1.00994 (10) | 0.09647 (7) | 0.01848 (19) | |
| H8BA | 1.1475 | 0.9396 | 0.0651 | 0.028* | |
| H8BB | 1.1704 | 1.0264 | 0.1452 | 0.028* | |
| H8BC | 1.1019 | 1.1012 | 0.0681 | 0.028* | |
| H1NB | 0.9739 (11) | 1.1378 (16) | 0.1584 (8) | 0.025 (3)* | |
| H1NA | 0.0217 (11) | 0.6354 (16) | 0.0901 (8) | 0.026 (3)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1A | 0.02335 (13) | 0.03545 (14) | 0.01876 (15) | −0.00052 (9) | −0.00167 (10) | −0.00159 (9) |
| S1A | 0.01605 (11) | 0.01243 (10) | 0.01325 (12) | 0.00092 (7) | 0.00468 (8) | 0.00067 (7) |
| O1A | 0.0248 (3) | 0.0179 (3) | 0.0203 (4) | −0.0010 (3) | 0.0084 (3) | 0.0060 (3) |
| O2A | 0.0240 (3) | 0.0163 (3) | 0.0169 (3) | 0.0032 (2) | 0.0043 (3) | −0.0037 (2) |
| O3A | 0.0202 (3) | 0.0117 (3) | 0.0232 (4) | −0.0001 (2) | 0.0038 (3) | 0.0033 (2) |
| N1A | 0.0165 (3) | 0.0101 (3) | 0.0179 (4) | 0.0015 (2) | 0.0050 (3) | 0.0020 (3) |
| C1A | 0.0213 (4) | 0.0135 (4) | 0.0215 (5) | 0.0011 (3) | 0.0024 (4) | −0.0019 (3) |
| C2A | 0.0220 (4) | 0.0175 (4) | 0.0219 (5) | 0.0002 (3) | 0.0022 (4) | −0.0048 (3) |
| C3A | 0.0146 (4) | 0.0225 (4) | 0.0165 (5) | −0.0007 (3) | 0.0024 (4) | −0.0009 (3) |
| C4A | 0.0175 (4) | 0.0177 (4) | 0.0196 (5) | −0.0004 (3) | 0.0027 (3) | 0.0028 (3) |
| C5A | 0.0166 (4) | 0.0135 (4) | 0.0190 (4) | −0.0004 (3) | 0.0029 (3) | 0.0010 (3) |
| C6A | 0.0148 (4) | 0.0132 (4) | 0.0154 (5) | 0.0002 (3) | 0.0040 (3) | −0.0007 (3) |
| C7A | 0.0156 (4) | 0.0129 (4) | 0.0137 (4) | −0.0015 (3) | 0.0023 (3) | 0.0001 (3) |
| C8A | 0.0176 (4) | 0.0199 (4) | 0.0196 (5) | 0.0018 (3) | 0.0071 (4) | 0.0023 (3) |
| Cl1B | 0.02278 (12) | 0.03587 (14) | 0.01794 (14) | −0.00114 (9) | −0.00155 (10) | −0.00122 (9) |
| S1B | 0.01612 (11) | 0.01213 (9) | 0.01342 (12) | −0.00106 (7) | 0.00458 (9) | −0.00113 (7) |
| O1B | 0.0222 (3) | 0.0182 (3) | 0.0193 (4) | 0.0006 (2) | 0.0067 (3) | −0.0061 (3) |
| O2B | 0.0251 (3) | 0.0159 (3) | 0.0181 (3) | −0.0030 (2) | 0.0044 (3) | 0.0039 (2) |
| O3B | 0.0216 (3) | 0.0118 (3) | 0.0227 (4) | 0.0011 (2) | 0.0033 (3) | −0.0030 (2) |
| N1B | 0.0169 (3) | 0.0099 (3) | 0.0179 (4) | −0.0010 (2) | 0.0055 (3) | −0.0013 (3) |
| C1B | 0.0198 (4) | 0.0125 (4) | 0.0187 (4) | −0.0007 (3) | 0.0047 (3) | 0.0005 (3) |
| C2B | 0.0192 (4) | 0.0173 (4) | 0.0193 (5) | 0.0000 (3) | 0.0032 (3) | 0.0028 (3) |
| C3B | 0.0143 (4) | 0.0227 (4) | 0.0162 (5) | −0.0008 (3) | 0.0024 (4) | −0.0006 (3) |
| C4B | 0.0174 (4) | 0.0177 (4) | 0.0203 (5) | −0.0007 (3) | 0.0019 (3) | −0.0051 (3) |
| C5B | 0.0167 (4) | 0.0127 (4) | 0.0200 (5) | 0.0001 (3) | 0.0027 (3) | −0.0022 (3) |
| C6B | 0.0148 (4) | 0.0125 (4) | 0.0157 (5) | −0.0008 (3) | 0.0048 (4) | −0.0010 (3) |
| C7B | 0.0160 (4) | 0.0126 (4) | 0.0140 (4) | 0.0022 (3) | 0.0022 (3) | 0.0004 (3) |
| C8B | 0.0172 (4) | 0.0192 (4) | 0.0204 (5) | −0.0004 (3) | 0.0071 (4) | −0.0006 (3) |
| Cl1A—C3A | 1.7394 (11) | Cl1B—C3B | 1.7375 (11) |
| S1A—O2A | 1.4295 (7) | S1B—O2B | 1.4286 (7) |
| S1A—O1A | 1.4366 (7) | S1B—O1B | 1.4339 (7) |
| S1A—N1A | 1.6537 (8) | S1B—N1B | 1.6559 (8) |
| S1A—C6A | 1.7591 (11) | S1B—C6B | 1.7593 (11) |
| O3A—C7A | 1.2200 (11) | O3B—C7B | 1.2206 (11) |
| N1A—C7A | 1.3839 (11) | N1B—C7B | 1.3823 (11) |
| N1A—H1NA | 0.865 (14) | N1B—H1NB | 0.871 (14) |
| C1A—C2A | 1.3873 (15) | C1B—C2B | 1.3855 (14) |
| C1A—C6A | 1.3943 (13) | C1B—C6B | 1.3949 (13) |
| C1A—H1AA | 0.9500 | C1B—H1BA | 0.9500 |
| C2A—C3A | 1.3907 (14) | C2B—C3B | 1.3895 (14) |
| C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
| C3A—C4A | 1.3864 (14) | C3B—C4B | 1.3887 (14) |
| C4A—C5A | 1.3897 (14) | C4B—C5B | 1.3925 (14) |
| C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
| C5A—C6A | 1.3913 (13) | C5B—C6B | 1.3934 (12) |
| C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
| C7A—C8A | 1.5012 (13) | C7B—C8B | 1.4998 (13) |
| C8A—H8AA | 0.9800 | C8B—H8BA | 0.9800 |
| C8A—H8AB | 0.9800 | C8B—H8BB | 0.9800 |
| C8A—H8AC | 0.9800 | C8B—H8BC | 0.9800 |
| O2A—S1A—O1A | 119.64 (5) | O2B—S1B—O1B | 119.73 (5) |
| O2A—S1A—N1A | 110.25 (4) | O2B—S1B—N1B | 110.14 (4) |
| O1A—S1A—N1A | 103.55 (4) | O1B—S1B—N1B | 103.54 (4) |
| O2A—S1A—C6A | 108.95 (4) | O2B—S1B—C6B | 109.19 (4) |
| O1A—S1A—C6A | 109.08 (4) | O1B—S1B—C6B | 108.77 (4) |
| N1A—S1A—C6A | 104.24 (4) | N1B—S1B—C6B | 104.31 (4) |
| C7A—N1A—S1A | 123.31 (6) | C7B—N1B—S1B | 122.73 (6) |
| C7A—N1A—H1NA | 120.8 (9) | C7B—N1B—H1NB | 120.4 (9) |
| S1A—N1A—H1NA | 114.7 (9) | S1B—N1B—H1NB | 115.7 (9) |
| C2A—C1A—C6A | 119.21 (9) | C2B—C1B—C6B | 119.35 (9) |
| C2A—C1A—H1AA | 120.4 | C2B—C1B—H1BA | 120.3 |
| C6A—C1A—H1AA | 120.4 | C6B—C1B—H1BA | 120.3 |
| C1A—C2A—C3A | 118.68 (9) | C1B—C2B—C3B | 118.81 (9) |
| C1A—C2A—H2AA | 120.7 | C1B—C2B—H2BA | 120.6 |
| C3A—C2A—H2AA | 120.7 | C3B—C2B—H2BA | 120.6 |
| C4A—C3A—C2A | 122.38 (10) | C4B—C3B—C2B | 122.34 (10) |
| C4A—C3A—Cl1A | 118.79 (8) | C4B—C3B—Cl1B | 118.92 (8) |
| C2A—C3A—Cl1A | 118.81 (8) | C2B—C3B—Cl1B | 118.73 (8) |
| C3A—C4A—C5A | 118.96 (9) | C3B—C4B—C5B | 118.85 (9) |
| C3A—C4A—H4AA | 120.5 | C3B—C4B—H4BA | 120.6 |
| C5A—C4A—H4AA | 120.5 | C5B—C4B—H4BA | 120.6 |
| C4A—C5A—C6A | 118.98 (9) | C4B—C5B—C6B | 119.03 (9) |
| C4A—C5A—H5AA | 120.5 | C4B—C5B—H5BA | 120.5 |
| C6A—C5A—H5AA | 120.5 | C6B—C5B—H5BA | 120.5 |
| C5A—C6A—C1A | 121.79 (9) | C5B—C6B—C1B | 121.61 (9) |
| C5A—C6A—S1A | 119.51 (7) | C5B—C6B—S1B | 120.13 (7) |
| C1A—C6A—S1A | 118.67 (7) | C1B—C6B—S1B | 118.23 (7) |
| O3A—C7A—N1A | 121.09 (8) | O3B—C7B—N1B | 120.88 (8) |
| O3A—C7A—C8A | 124.21 (8) | O3B—C7B—C8B | 124.43 (8) |
| N1A—C7A—C8A | 114.69 (8) | N1B—C7B—C8B | 114.68 (8) |
| C7A—C8A—H8AA | 109.5 | C7B—C8B—H8BA | 109.5 |
| C7A—C8A—H8AB | 109.5 | C7B—C8B—H8BB | 109.5 |
| H8AA—C8A—H8AB | 109.5 | H8BA—C8B—H8BB | 109.5 |
| C7A—C8A—H8AC | 109.5 | C7B—C8B—H8BC | 109.5 |
| H8AA—C8A—H8AC | 109.5 | H8BA—C8B—H8BC | 109.5 |
| H8AB—C8A—H8AC | 109.5 | H8BB—C8B—H8BC | 109.5 |
| O2A—S1A—N1A—C7A | 50.89 (9) | O2B—S1B—N1B—C7B | 51.56 (9) |
| O1A—S1A—N1A—C7A | −179.98 (8) | O1B—S1B—N1B—C7B | −179.27 (8) |
| C6A—S1A—N1A—C7A | −65.90 (8) | C6B—S1B—N1B—C7B | −65.50 (8) |
| C6A—C1A—C2A—C3A | −0.07 (15) | C6B—C1B—C2B—C3B | 0.04 (14) |
| C1A—C2A—C3A—C4A | 0.83 (16) | C1B—C2B—C3B—C4B | 1.14 (16) |
| C1A—C2A—C3A—Cl1A | −177.29 (8) | C1B—C2B—C3B—Cl1B | −177.27 (7) |
| C2A—C3A—C4A—C5A | −1.11 (16) | C2B—C3B—C4B—C5B | −1.32 (16) |
| Cl1A—C3A—C4A—C5A | 177.02 (7) | Cl1B—C3B—C4B—C5B | 177.08 (8) |
| C3A—C4A—C5A—C6A | 0.60 (15) | C3B—C4B—C5B—C6B | 0.32 (15) |
| C4A—C5A—C6A—C1A | 0.14 (15) | C4B—C5B—C6B—C1B | 0.83 (15) |
| C4A—C5A—C6A—S1A | −177.64 (7) | C4B—C5B—C6B—S1B | −177.14 (7) |
| C2A—C1A—C6A—C5A | −0.41 (15) | C2B—C1B—C6B—C5B | −1.02 (15) |
| C2A—C1A—C6A—S1A | 177.39 (8) | C2B—C1B—C6B—S1B | 176.99 (7) |
| O2A—S1A—C6A—C5A | −18.56 (9) | O2B—S1B—C6B—C5B | −21.27 (9) |
| O1A—S1A—C6A—C5A | −150.79 (8) | O1B—S1B—C6B—C5B | −153.56 (8) |
| N1A—S1A—C6A—C5A | 99.12 (8) | N1B—S1B—C6B—C5B | 96.44 (8) |
| O2A—S1A—C6A—C1A | 163.58 (8) | O2B—S1B—C6B—C1B | 160.70 (8) |
| O1A—S1A—C6A—C1A | 31.36 (9) | O1B—S1B—C6B—C1B | 28.41 (9) |
| N1A—S1A—C6A—C1A | −78.73 (8) | N1B—S1B—C6B—C1B | −81.59 (8) |
| S1A—N1A—C7A—O3A | −3.57 (13) | S1B—N1B—C7B—O3B | −1.87 (13) |
| S1A—N1A—C7A—C8A | 175.90 (7) | S1B—N1B—C7B—C8B | 177.08 (7) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1B—H1NB···O3Ai | 0.871 (15) | 1.939 (15) | 2.7980 (10) | 168.6 (13) |
| N1A—H1NA···O3Bii | 0.865 (15) | 1.939 (15) | 2.7952 (10) | 170.0 (13) |
| Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1B—H1NB···O3Ai | 0.871 (15) | 1.939 (15) | 2.7980 (10) | 168.6 (13) |
| N1A—H1NA···O3Bii | 0.865 (15) | 1.939 (15) | 2.7952 (10) | 170.0 (13) |
| Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z. |
HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors are grateful to the Visvesvaraya Technological University, Jnana Sangama, Belgaum, for financial support through research project grant No. VTU/Aca./2010–11/A-9/11330 Dtd. 07–12–2010.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
Fun, H.-K., Chia, T. S., Hegde, P., Jyothi, K. & D'Souza, P. R. (2012). Acta Cryst. E68, o2025.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
In continuation to our reports on the biological activity of sulfonamide containing compounds (Fun et al., 2012), we report herein the crystal structure of the title compound.
The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules (A and B). The C═ O and N—H bonds in the amide planes [C7A/O3A/N1A/H1NA and C7B/O3B/N1B/H1NB; maximum deviations = 0.043 (5) Å at atom N1A and 0.047 (5) Å at atom H1NB] are trans to each other. The benzene ring (C1–C6) forms a dihedral angle of 87.6 (3)° with the amide plane in molecule A, whereas the corresponding angle is 86.0 (3)° in molecule B. The bond lengths and angles are comparable to those found in a related structure (Fun et al., 2012). In the crystal (Fig. 2), molecules are linked by intermolecular N1B—H1NB···O3A and N1A—H1NA···O3B hydrogen bonds (Table 1) into an infinite chain along the b axis. Short intermolecular Cl1A···Cl1A [3.2882 (5) Å; 1 - x, 1 - y, 1 - z] and Cl1B···Cl1B [3.2812 (5) Å; 1 - x, y, -1/2 - z] are also observed.