organic compounds
4-Chloro-N-(3,5-dimethylphenyl)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
The 14H14ClNO2S, contains two independent molecules, which are twisted at the S atoms with C—SO2—NH—C torsion angles of −69.4 (7)° and 66.0 (8)°. The sulfonyl and the anilino benzene rings are tilted relative to each other by 49.0 (4) and 61.7 (3)° in the two molecules. In the crystal, the molecules are linked into chains by N—H⋯O hydrogen bonds.
of the title compound, CRelated literature
For hydrogen-bonding modes of ). For our studies of the effect of substituents on the structures of N-(aryl)-amides, see: Gowda et al. (2006), on N-(aryl)arylsulfonamides, see: Nirmala et al. (2009); Shakuntala et al. (2011a,b) and on N-(aryl)methanesulfonamides, see: Gowda et al. (2007).
see: Adsmond & Grant (2001Experimental
Crystal data
|
Refinement
|
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
10.1107/S1600536811028819/ds2123sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811028819/ds2123Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811028819/ds2123Isup3.cml
The solution of chlorobenzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 4-chlorobenzenesulfonylchloride was treated with 3,5-dimethylaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant 4-chloro-N-(3,5-dimethylphenyl)-benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from aqueous ethanol. The compound was characterized by recording its infrared and NMR spectra.
Prism like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.
The H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å, methyl C—H = 0.96 Å, N—H = 0.86 Å and were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
The residual electron-density features are located in the region of H1A and S1. The highest peak is 1.31 Å from H1A and the deepest hole is 1.09 Å from S1. To improve considerably values of R1, wR2, and GOOF these bad four reflections (4 3 10 2 2 7 2 2 5 2 3 4) were omitted from the refinement.
The crystals available for X-ray studies were of rather poor quality and weak scatterers at high theta value resulting in relatively high R values.
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).C14H14ClNO2S | F(000) = 2464 |
Mr = 295.77 | Dx = 1.347 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2329 reflections |
a = 21.990 (2) Å | θ = 2.5–27.8° |
b = 10.0470 (8) Å | µ = 0.40 mm−1 |
c = 26.408 (2) Å | T = 293 K |
V = 5834.4 (8) Å3 | Prism, colourless |
Z = 16 | 0.40 × 0.20 × 0.06 mm |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 5320 independent reflections |
Radiation source: fine-focus sealed tube | 2694 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.106 |
Rotation method data acquisition using ω scans. | θmax = 25.4°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −26→26 |
Tmin = 0.856, Tmax = 0.976 | k = −9→12 |
21403 measured reflections | l = −25→31 |
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)] = 0.128 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.345 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1148P)2 + 41.4199P] where P = (Fo2 + 2Fc2)/3 |
5320 reflections | (Δ/σ)max = 0.003 |
347 parameters | Δρmax = 1.06 e Å−3 |
1 restraint | Δρmin = −0.41 e Å−3 |
C14H14ClNO2S | V = 5834.4 (8) Å3 |
Mr = 295.77 | Z = 16 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 21.990 (2) Å | µ = 0.40 mm−1 |
b = 10.0470 (8) Å | T = 293 K |
c = 26.408 (2) Å | 0.40 × 0.20 × 0.06 mm |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 5320 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2694 reflections with I > 2σ(I) |
Tmin = 0.856, Tmax = 0.976 | Rint = 0.106 |
21403 measured reflections |
R[F2 > 2σ(F2)] = 0.128 | 1 restraint |
wR(F2) = 0.345 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1148P)2 + 41.4199P] where P = (Fo2 + 2Fc2)/3 |
5320 reflections | Δρmax = 1.06 e Å−3 |
347 parameters | Δρmin = −0.41 e Å−3 |
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 | ||
Cl1 | 0.00034 (14) | 0.0421 (4) | 0.59314 (17) | 0.1103 (14) | |
S1 | 0.26317 (10) | 0.0246 (2) | 0.50757 (9) | 0.0454 (6) | |
O1 | 0.3036 (3) | 0.0914 (6) | 0.5418 (2) | 0.0544 (17) | |
O2 | 0.2769 (3) | −0.1061 (6) | 0.4911 (3) | 0.0547 (17) | |
N1 | 0.2594 (3) | 0.1192 (7) | 0.4583 (3) | 0.0456 (18) | |
H1A | 0.2778 | 0.1947 | 0.4587 | 0.055* | |
C1 | 0.1902 (4) | 0.0237 (9) | 0.5340 (3) | 0.047 (2) | |
C2 | 0.1472 (5) | −0.0646 (11) | 0.5157 (5) | 0.070 (3) | |
H2 | 0.1570 | −0.1267 | 0.4910 | 0.084* | |
C3 | 0.0889 (5) | −0.0574 (12) | 0.5355 (5) | 0.082 (4) | |
H3 | 0.0593 | −0.1163 | 0.5242 | 0.098* | |
C4 | 0.0746 (5) | 0.0348 (11) | 0.5713 (5) | 0.065 (3) | |
C5 | 0.1174 (5) | 0.1204 (11) | 0.5888 (4) | 0.069 (3) | |
H5 | 0.1075 | 0.1818 | 0.6138 | 0.083* | |
C6 | 0.1749 (4) | 0.1166 (10) | 0.5699 (4) | 0.056 (3) | |
H6 | 0.2039 | 0.1770 | 0.5814 | 0.068* | |
C7 | 0.2264 (3) | 0.0807 (8) | 0.4140 (3) | 0.037 (2) | |
C8 | 0.1732 (4) | 0.1481 (9) | 0.4019 (3) | 0.044 (2) | |
H8 | 0.1583 | 0.2126 | 0.4239 | 0.053* | |
C9 | 0.1421 (4) | 0.1212 (10) | 0.3577 (4) | 0.049 (2) | |
C10 | 0.1645 (4) | 0.0205 (10) | 0.3270 (4) | 0.054 (2) | |
H10 | 0.1435 | −0.0003 | 0.2974 | 0.065* | |
C11 | 0.2166 (5) | −0.0504 (10) | 0.3383 (4) | 0.057 (3) | |
C12 | 0.2471 (4) | −0.0189 (9) | 0.3823 (3) | 0.049 (2) | |
H12 | 0.2822 | −0.0655 | 0.3907 | 0.058* | |
C13 | 0.0873 (4) | 0.2025 (12) | 0.3421 (4) | 0.074 (3) | |
H13A | 0.0989 | 0.2941 | 0.3383 | 0.088* | |
H13B | 0.0563 | 0.1954 | 0.3676 | 0.088* | |
H13C | 0.0717 | 0.1697 | 0.3105 | 0.088* | |
C14 | 0.2416 (5) | −0.1558 (11) | 0.3035 (4) | 0.070 (3) | |
H14A | 0.2404 | −0.1242 | 0.2693 | 0.084* | |
H14B | 0.2174 | −0.2350 | 0.3064 | 0.084* | |
H14C | 0.2828 | −0.1754 | 0.3128 | 0.084* | |
Cl2 | 0.09120 (19) | 0.4163 (3) | 0.22721 (16) | 0.1050 (13) | |
S2 | 0.13516 (12) | 1.0127 (3) | 0.17349 (10) | 0.0600 (8) | |
O3 | 0.1989 (3) | 1.0367 (8) | 0.1698 (3) | 0.085 (2) | |
O4 | 0.0976 (4) | 1.0924 (8) | 0.2066 (3) | 0.081 (2) | |
N2 | 0.1092 (3) | 1.0317 (8) | 0.1159 (3) | 0.0504 (19) | |
H2A | 0.1342 | 1.0514 | 0.0920 | 0.061* | |
C15 | 0.1242 (4) | 0.8416 (10) | 0.1887 (3) | 0.048 (2) | |
C16 | 0.1665 (5) | 0.7509 (12) | 0.1776 (4) | 0.065 (3) | |
H16 | 0.2030 | 0.7759 | 0.1625 | 0.078* | |
C17 | 0.1549 (5) | 0.6177 (11) | 0.1893 (4) | 0.069 (3) | |
H17 | 0.1832 | 0.5524 | 0.1809 | 0.083* | |
C18 | 0.1036 (5) | 0.5848 (11) | 0.2123 (4) | 0.062 (3) | |
C19 | 0.0606 (5) | 0.6750 (12) | 0.2248 (4) | 0.071 (3) | |
H19 | 0.0243 | 0.6488 | 0.2398 | 0.085* | |
C20 | 0.0720 (4) | 0.8036 (11) | 0.2150 (4) | 0.058 (3) | |
H20 | 0.0447 | 0.8683 | 0.2258 | 0.070* | |
C21 | 0.0456 (4) | 1.0162 (9) | 0.1041 (3) | 0.042 (2) | |
C22 | 0.0300 (4) | 0.9218 (9) | 0.0686 (3) | 0.044 (2) | |
H22 | 0.0596 | 0.8654 | 0.0556 | 0.053* | |
C23 | −0.0305 (4) | 0.9104 (9) | 0.0518 (3) | 0.046 (2) | |
C24 | −0.0726 (4) | 0.9957 (9) | 0.0725 (4) | 0.052 (2) | |
H24 | −0.1127 | 0.9909 | 0.0615 | 0.063* | |
C25 | −0.0572 (4) | 1.0907 (9) | 0.1101 (4) | 0.050 (2) | |
C26 | 0.0030 (4) | 1.0975 (9) | 0.1251 (3) | 0.044 (2) | |
H26 | 0.0144 | 1.1584 | 0.1498 | 0.053* | |
C27 | −0.0480 (4) | 0.8106 (10) | 0.0130 (4) | 0.057 (3) | |
H27A | −0.0597 | 0.7292 | 0.0293 | 0.068* | |
H27B | −0.0141 | 0.7940 | −0.0090 | 0.068* | |
H27C | −0.0815 | 0.8440 | −0.0066 | 0.068* | |
C28 | −0.1049 (5) | 1.1804 (13) | 0.1316 (5) | 0.086 (4) | |
H28A | −0.1370 | 1.1277 | 0.1459 | 0.104* | |
H28B | −0.1210 | 1.2359 | 0.1052 | 0.104* | |
H28C | −0.0872 | 1.2352 | 0.1575 | 0.104* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0679 (19) | 0.107 (3) | 0.156 (4) | −0.008 (2) | 0.046 (2) | 0.006 (3) |
S1 | 0.0432 (12) | 0.0429 (13) | 0.0501 (13) | 0.0036 (10) | −0.0105 (10) | −0.0032 (11) |
O1 | 0.046 (4) | 0.060 (4) | 0.057 (4) | 0.001 (3) | −0.022 (3) | −0.009 (3) |
O2 | 0.065 (4) | 0.039 (4) | 0.061 (4) | 0.008 (3) | −0.010 (3) | −0.001 (3) |
N1 | 0.047 (4) | 0.053 (5) | 0.037 (4) | −0.011 (3) | −0.007 (3) | −0.006 (4) |
C1 | 0.049 (5) | 0.041 (5) | 0.051 (5) | −0.003 (4) | −0.013 (4) | 0.000 (5) |
C2 | 0.053 (6) | 0.066 (7) | 0.091 (8) | −0.006 (5) | −0.001 (6) | −0.022 (6) |
C3 | 0.058 (7) | 0.069 (8) | 0.119 (11) | −0.021 (6) | −0.001 (7) | −0.015 (8) |
C4 | 0.059 (6) | 0.046 (6) | 0.091 (8) | 0.005 (5) | 0.013 (6) | 0.011 (6) |
C5 | 0.076 (8) | 0.064 (7) | 0.067 (7) | −0.007 (6) | 0.013 (6) | −0.013 (6) |
C6 | 0.054 (6) | 0.067 (7) | 0.048 (6) | −0.004 (5) | 0.002 (5) | −0.005 (5) |
C7 | 0.031 (4) | 0.036 (5) | 0.044 (5) | −0.004 (4) | −0.008 (4) | 0.005 (4) |
C8 | 0.043 (5) | 0.046 (5) | 0.043 (5) | 0.001 (4) | −0.004 (4) | −0.005 (4) |
C9 | 0.038 (5) | 0.063 (6) | 0.046 (5) | 0.002 (4) | 0.000 (4) | 0.006 (5) |
C10 | 0.053 (6) | 0.065 (7) | 0.044 (5) | −0.002 (5) | −0.014 (4) | 0.004 (5) |
C11 | 0.066 (6) | 0.061 (6) | 0.045 (6) | −0.003 (5) | 0.000 (5) | −0.006 (5) |
C12 | 0.049 (5) | 0.053 (6) | 0.044 (5) | 0.008 (5) | −0.006 (4) | 0.004 (5) |
C13 | 0.049 (6) | 0.094 (9) | 0.079 (8) | 0.009 (6) | −0.012 (5) | 0.016 (7) |
C14 | 0.080 (7) | 0.075 (8) | 0.054 (6) | 0.009 (6) | −0.010 (6) | −0.021 (6) |
Cl2 | 0.124 (3) | 0.075 (2) | 0.116 (3) | −0.007 (2) | −0.004 (2) | 0.035 (2) |
S2 | 0.0554 (15) | 0.0633 (17) | 0.0614 (16) | −0.0026 (13) | −0.0178 (13) | −0.0092 (14) |
O3 | 0.048 (4) | 0.096 (6) | 0.111 (6) | −0.020 (4) | −0.028 (4) | 0.009 (5) |
O4 | 0.103 (6) | 0.087 (6) | 0.052 (4) | 0.022 (5) | −0.020 (4) | −0.028 (4) |
N2 | 0.038 (4) | 0.068 (5) | 0.046 (4) | −0.007 (4) | −0.002 (3) | 0.007 (4) |
C15 | 0.049 (5) | 0.053 (6) | 0.041 (5) | 0.004 (5) | −0.019 (4) | 0.002 (5) |
C16 | 0.061 (6) | 0.072 (8) | 0.063 (7) | −0.004 (6) | −0.001 (5) | −0.012 (6) |
C17 | 0.075 (8) | 0.063 (7) | 0.070 (8) | 0.021 (6) | 0.010 (6) | −0.004 (6) |
C18 | 0.069 (7) | 0.069 (7) | 0.049 (6) | 0.004 (6) | 0.001 (5) | 0.008 (5) |
C19 | 0.058 (6) | 0.079 (6) | 0.074 (8) | −0.003 (6) | 0.003 (6) | 0.017 (7) |
C20 | 0.051 (6) | 0.066 (5) | 0.059 (6) | 0.005 (5) | 0.010 (5) | −0.012 (5) |
C21 | 0.041 (5) | 0.042 (5) | 0.044 (5) | −0.002 (4) | 0.004 (4) | 0.007 (4) |
C22 | 0.044 (5) | 0.046 (5) | 0.043 (5) | 0.005 (4) | 0.005 (4) | 0.004 (4) |
C23 | 0.037 (5) | 0.052 (6) | 0.048 (5) | 0.000 (4) | 0.001 (4) | 0.002 (5) |
C24 | 0.042 (5) | 0.057 (6) | 0.057 (6) | 0.000 (4) | −0.002 (4) | 0.004 (5) |
C25 | 0.042 (5) | 0.058 (6) | 0.050 (6) | 0.010 (4) | 0.009 (4) | −0.005 (5) |
C26 | 0.045 (5) | 0.046 (6) | 0.042 (5) | 0.000 (4) | 0.003 (4) | −0.009 (4) |
C27 | 0.054 (6) | 0.058 (6) | 0.058 (6) | 0.002 (5) | −0.008 (5) | −0.005 (5) |
C28 | 0.065 (7) | 0.093 (9) | 0.102 (10) | 0.019 (7) | −0.003 (7) | −0.021 (8) |
Cl1—C4 | 1.732 (10) | Cl2—C18 | 1.760 (11) |
S1—O2 | 1.416 (6) | S2—O3 | 1.425 (7) |
S1—O1 | 1.434 (6) | S2—O4 | 1.445 (8) |
S1—N1 | 1.613 (7) | S2—N2 | 1.636 (7) |
S1—C1 | 1.750 (9) | S2—C15 | 1.782 (10) |
N1—C7 | 1.429 (10) | N2—C21 | 1.442 (10) |
N1—H1A | 0.8600 | N2—H2A | 0.8600 |
C1—C6 | 1.374 (13) | C15—C16 | 1.335 (13) |
C1—C2 | 1.383 (13) | C15—C20 | 1.394 (13) |
C2—C3 | 1.384 (14) | C16—C17 | 1.396 (15) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.361 (16) | C17—C18 | 1.323 (15) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.357 (15) | C18—C19 | 1.351 (15) |
C5—C6 | 1.360 (13) | C19—C20 | 1.342 (14) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C12 | 1.382 (12) | C21—C26 | 1.361 (11) |
C7—C8 | 1.390 (11) | C21—C22 | 1.378 (12) |
C8—C9 | 1.380 (12) | C22—C23 | 1.406 (12) |
C8—H8 | 0.9300 | C22—H22 | 0.9300 |
C9—C10 | 1.387 (13) | C23—C24 | 1.376 (12) |
C9—C13 | 1.513 (12) | C23—C27 | 1.485 (12) |
C10—C11 | 1.382 (13) | C24—C25 | 1.417 (13) |
C10—H10 | 0.9300 | C24—H24 | 0.9300 |
C11—C12 | 1.377 (12) | C25—C26 | 1.383 (12) |
C11—C14 | 1.505 (13) | C25—C28 | 1.495 (13) |
C12—H12 | 0.9300 | C26—H26 | 0.9300 |
C13—H13A | 0.9600 | C27—H27A | 0.9600 |
C13—H13B | 0.9600 | C27—H27B | 0.9600 |
C13—H13C | 0.9600 | C27—H27C | 0.9600 |
C14—H14A | 0.9600 | C28—H28A | 0.9600 |
C14—H14B | 0.9600 | C28—H28B | 0.9600 |
C14—H14C | 0.9600 | C28—H28C | 0.9600 |
O2—S1—O1 | 119.7 (4) | O3—S2—O4 | 120.6 (5) |
O2—S1—N1 | 108.0 (4) | O3—S2—N2 | 105.0 (5) |
O1—S1—N1 | 105.4 (4) | O4—S2—N2 | 107.4 (4) |
O2—S1—C1 | 108.2 (4) | O3—S2—C15 | 108.2 (5) |
O1—S1—C1 | 108.6 (4) | O4—S2—C15 | 108.7 (5) |
N1—S1—C1 | 106.1 (4) | N2—S2—C15 | 106.0 (4) |
C7—N1—S1 | 121.8 (6) | C21—N2—S2 | 121.8 (6) |
C7—N1—H1A | 119.1 | C21—N2—H2A | 119.1 |
S1—N1—H1A | 119.1 | S2—N2—H2A | 119.1 |
C6—C1—C2 | 120.6 (9) | C16—C15—C20 | 119.8 (10) |
C6—C1—S1 | 119.7 (7) | C16—C15—S2 | 120.9 (8) |
C2—C1—S1 | 119.5 (8) | C20—C15—S2 | 119.2 (8) |
C3—C2—C1 | 117.9 (10) | C15—C16—C17 | 118.6 (10) |
C3—C2—H2 | 121.1 | C15—C16—H16 | 120.7 |
C1—C2—H2 | 121.1 | C17—C16—H16 | 120.7 |
C4—C3—C2 | 120.8 (10) | C18—C17—C16 | 119.7 (10) |
C4—C3—H3 | 119.6 | C18—C17—H17 | 120.1 |
C2—C3—H3 | 119.6 | C16—C17—H17 | 120.1 |
C5—C4—C3 | 120.4 (10) | C17—C18—C19 | 122.8 (11) |
C5—C4—Cl1 | 121.0 (9) | C17—C18—Cl2 | 118.4 (9) |
C3—C4—Cl1 | 118.6 (9) | C19—C18—Cl2 | 118.7 (9) |
C4—C5—C6 | 120.3 (11) | C20—C19—C18 | 117.8 (11) |
C4—C5—H5 | 119.9 | C20—C19—H19 | 121.1 |
C6—C5—H5 | 119.9 | C18—C19—H19 | 121.1 |
C5—C6—C1 | 119.9 (10) | C19—C20—C15 | 120.9 (10) |
C5—C6—H6 | 120.0 | C19—C20—H20 | 119.5 |
C1—C6—H6 | 120.0 | C15—C20—H20 | 119.5 |
C12—C7—C8 | 119.3 (8) | C26—C21—C22 | 121.3 (8) |
C12—C7—N1 | 121.7 (7) | C26—C21—N2 | 121.0 (8) |
C8—C7—N1 | 119.0 (8) | C22—C21—N2 | 117.6 (8) |
C9—C8—C7 | 121.2 (8) | C21—C22—C23 | 120.4 (8) |
C9—C8—H8 | 119.4 | C21—C22—H22 | 119.8 |
C7—C8—H8 | 119.4 | C23—C22—H22 | 119.8 |
C8—C9—C10 | 117.4 (8) | C24—C23—C22 | 117.3 (9) |
C8—C9—C13 | 121.3 (9) | C24—C23—C27 | 121.5 (8) |
C10—C9—C13 | 121.2 (9) | C22—C23—C27 | 121.2 (8) |
C11—C10—C9 | 122.9 (9) | C23—C24—C25 | 122.6 (8) |
C11—C10—H10 | 118.5 | C23—C24—H24 | 118.7 |
C9—C10—H10 | 118.5 | C25—C24—H24 | 118.7 |
C12—C11—C10 | 117.9 (9) | C26—C25—C24 | 117.5 (8) |
C12—C11—C14 | 119.9 (9) | C26—C25—C28 | 122.2 (9) |
C10—C11—C14 | 122.2 (9) | C24—C25—C28 | 120.3 (9) |
C11—C12—C7 | 121.2 (9) | C21—C26—C25 | 120.8 (8) |
C11—C12—H12 | 119.4 | C21—C26—H26 | 119.6 |
C7—C12—H12 | 119.4 | C25—C26—H26 | 119.6 |
C9—C13—H13A | 109.5 | C23—C27—H27A | 109.5 |
C9—C13—H13B | 109.5 | C23—C27—H27B | 109.5 |
H13A—C13—H13B | 109.5 | H27A—C27—H27B | 109.5 |
C9—C13—H13C | 109.5 | C23—C27—H27C | 109.5 |
H13A—C13—H13C | 109.5 | H27A—C27—H27C | 109.5 |
H13B—C13—H13C | 109.5 | H27B—C27—H27C | 109.5 |
C11—C14—H14A | 109.5 | C25—C28—H28A | 109.5 |
C11—C14—H14B | 109.5 | C25—C28—H28B | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28B | 109.5 |
C11—C14—H14C | 109.5 | C25—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
H14B—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
O2—S1—N1—C7 | 46.5 (7) | O3—S2—N2—C21 | −179.5 (7) |
O1—S1—N1—C7 | 175.5 (6) | O4—S2—N2—C21 | −50.1 (8) |
C1—S1—N1—C7 | −69.4 (7) | C15—S2—N2—C21 | 66.0 (8) |
O2—S1—C1—C6 | 153.8 (7) | O3—S2—C15—C16 | −23.8 (9) |
O1—S1—C1—C6 | 22.4 (9) | O4—S2—C15—C16 | −156.4 (8) |
N1—S1—C1—C6 | −90.5 (8) | N2—S2—C15—C16 | 88.4 (8) |
O2—S1—C1—C2 | −30.9 (9) | O3—S2—C15—C20 | 152.8 (8) |
O1—S1—C1—C2 | −162.3 (8) | O4—S2—C15—C20 | 20.2 (9) |
N1—S1—C1—C2 | 84.8 (9) | N2—S2—C15—C20 | −95.0 (8) |
C6—C1—C2—C3 | −1.1 (16) | C20—C15—C16—C17 | 5.0 (15) |
S1—C1—C2—C3 | −176.4 (9) | S2—C15—C16—C17 | −178.4 (8) |
C1—C2—C3—C4 | 0.8 (19) | C15—C16—C17—C18 | −2.1 (17) |
C2—C3—C4—C5 | −0.9 (19) | C16—C17—C18—C19 | 0.9 (18) |
C2—C3—C4—Cl1 | 178.0 (10) | C16—C17—C18—Cl2 | −179.0 (9) |
C3—C4—C5—C6 | 1.3 (18) | C17—C18—C19—C20 | −2.5 (18) |
Cl1—C4—C5—C6 | −177.5 (9) | Cl2—C18—C19—C20 | 177.3 (9) |
C4—C5—C6—C1 | −1.7 (17) | C18—C19—C20—C15 | 5.4 (17) |
C2—C1—C6—C5 | 1.6 (15) | C16—C15—C20—C19 | −6.8 (15) |
S1—C1—C6—C5 | 176.9 (8) | S2—C15—C20—C19 | 176.5 (9) |
S1—N1—C7—C12 | −71.4 (10) | S2—N2—C21—C26 | 62.2 (11) |
S1—N1—C7—C8 | 110.6 (8) | S2—N2—C21—C22 | −121.8 (8) |
C12—C7—C8—C9 | −2.7 (13) | C26—C21—C22—C23 | 2.1 (13) |
N1—C7—C8—C9 | 175.3 (8) | N2—C21—C22—C23 | −173.9 (8) |
C7—C8—C9—C10 | 2.7 (13) | C21—C22—C23—C24 | −0.5 (13) |
C7—C8—C9—C13 | −174.6 (9) | C21—C22—C23—C27 | 179.1 (8) |
C8—C9—C10—C11 | −1.5 (14) | C22—C23—C24—C25 | −1.2 (14) |
C13—C9—C10—C11 | 175.9 (10) | C27—C23—C24—C25 | 179.2 (9) |
C9—C10—C11—C12 | 0.2 (15) | C23—C24—C25—C26 | 1.2 (14) |
C9—C10—C11—C14 | −177.6 (9) | C23—C24—C25—C28 | −179.6 (10) |
C10—C11—C12—C7 | −0.2 (15) | C22—C21—C26—C25 | −2.1 (14) |
C14—C11—C12—C7 | 177.7 (9) | N2—C21—C26—C25 | 173.8 (8) |
C8—C7—C12—C11 | 1.4 (13) | C24—C25—C26—C21 | 0.4 (14) |
N1—C7—C12—C11 | −176.6 (9) | C28—C25—C26—C21 | −178.7 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.86 | 2.49 | 3.001 (9) | 119 |
N2—H2A···O1ii | 0.86 | 2.39 | 3.006 (9) | 130 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H14ClNO2S |
Mr | 295.77 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 21.990 (2), 10.0470 (8), 26.408 (2) |
V (Å3) | 5834.4 (8) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.40 × 0.20 × 0.06 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.856, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21403, 5320, 2694 |
Rint | 0.106 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.128, 0.345, 1.07 |
No. of reflections | 5320 |
No. of parameters | 347 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.1148P)2 + 41.4199P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.06, −0.41 |
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—H1A···O2i | 0.86 | 2.49 | 3.001 (9) | 119.2 |
N2—H2A···O1ii | 0.86 | 2.39 | 3.006 (9) | 129.5 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, −y+1, z−1/2. |
Acknowledgements
KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.
References
Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2339. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Kozisek, J. & Fuess, H. (2006). Z. Naturforsch. Teil A, 55, 588–594. Google Scholar
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3225. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Shakuntala, K., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o1252. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shakuntala, K., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o1541. Web of Science CSD CrossRef IUCr Journals 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
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.
The sulfonamide moieties are the constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As a part of our work on the substituent effects on the structures and other aspects of this class of compounds (Gowda et al., 2006, 2007; Nirmala et al., 2009; Shakuntala et al., 2011a,b), in the present work, the crystal structure of 4-chloro-N-(3,5-dimethylphenyl)- benzenesulfonamide (I) has been determined (Fig.1). The asymmetric unit of the structure contains two independent molecules. The molecules are twisted at the S atoms with the C—SO2—NH—C torsion angles of -69.5 (7)° and 66.1 (8)° in the two molecules, compared to the values of 65.3 (2)° and 54.6 (2)° in the two independent molecules of 4-chloro-N-(2,5-dimethylphenyl)-benzenesulfonamide (II) (Shakuntala et al., 2011b), and -53.8 (3)° and -63.4 (3)° in the two molecules of 4-chloro-N-(phenyl)-benzenesulfonamide (III) (Shakuntala et al., 2011a) and 67.9 (2)° in N-(3,5-dimethylphenyl)benzenesulfonamide (IV)(Nirmala et al., 2009).
The sulfonyl and the anilino benzene rings in the two independent molecules of (I) are tilted relative to each other by 49.0 (4)° (molecule 1) and 61.7 (3)° (molecule 2), compared to the values of 59.3 (1)° (molecule 1) and 45.8 (1)° (molecule 2) in (II), -53.8 (3)° and -63.4 (3)° in the two independent molecules of (III), and 54.6 (1)° in (IV)
In the title compound the molecules are linked into chains by N—H···O(S) hydrogen bonding (Table 1 and Fig.2).