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Acta Cryst. (2010). E66, o1501    [ doi:10.1107/S1600536810019501 ]

4-Chloro-N-(4-methylbenzoyl)benzenesulfonamide

P. A. Suchetan, B. T. Gowda, S. Foro and H. Fuess

Abstract top

In the title compound, C14H12ClNO3S, the conformation of the N-H bond in the C-SO2-NH-C(O) segment is anti to the C=O bond. The molecule is twisted at the S atom with a torsion angle of 69.0 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO2-NH-C-O segment is 77.2 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.5 (1)°. In the structure, molecules are linked into chains via N-H...O hydrogen bonds, forming inversion dimers.

Comment top

As a part of studying the effect of ring and the side chain substituents on the crystal structures of N-aromatic sulfonamides(Gowda et al., 2009; Suchetan et al., 2010a,b,c), the structure of N-(4-methylbenzoyl)-4-chlorobenzenesulfonamide (I) has been determined. 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 those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(benzoyl)-4-chlorobenzenesulfonamide (III) (Suchetan et al., 2010b), N-(4-chlorobenzoyl)-4-methylbenzenesulfonamide (IV) (Suchetan et al., 2010a), and N-(4-chlorobenzoyl)- 4-chlorobenzenesulfonamide (V)(Suchetan et al., 2010c).

The molecules are twisted at the S atoms with the torsional angle of 69.0 (2)°, compared to the values of -66.9 (3)° in (II), -70.0 (2)° & 61.3 (2)° in the two molecules of (III), 67.1 (2)° (molecule 1) & 67.7 (2)° (molecule 2) in (IV) and 67.5 (3)° in (V).

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 77.2 (1)°, compared to the values of 86.5 (1)° in (II), 72.0 (1)° and 77.3 (1)° in the two molecules of (III), 83.6 (1)° (molecule 1) & 81.0 (1)° (molecule 2) in (IV) and 79.0 (1)° in (V)

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 89.5 (1)°, compared to the values of 80.3 (1) in (II), 62.8 (1)° (molecule 1) & 78.6 (1)° (molecule 2) in (III), 81.0 (1)° (molecule 1) and 76.3 (1)° (molecule 2) in (IV) and 85.6 (1)° in (V).

The packing of molecules linked by of N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009); Suchetan et al. (2010a,b,c).

Experimental top

The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, 4-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.

Rod 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.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (1) %A. The other H atoms were positioned with idealized geometry 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).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom- labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.
4-Chloro-N-(4-methylbenzoyl)benzenesulfonamide top
Crystal data top
C14H12ClNO3SF(000) = 1280
Mr = 309.76Dx = 1.469 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2077 reflections
a = 13.719 (1) Åθ = 2.6–27.8°
b = 9.6781 (9) ŵ = 0.43 mm−1
c = 21.102 (2) ÅT = 299 K
V = 2801.8 (4) Å3Rod, colourless
Z = 80.34 × 0.24 × 0.14 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2840 independent reflections
Radiation source: fine-focus sealed tube1902 reflections with I > 2σ(I)
graphiteRint = 0.018
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −13→17
Tmin = 0.868, Tmax = 0.943k = −7→12
6658 measured reflectionsl = −26→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0556P)2 + 1.3127P]
where P = (Fo2 + 2Fc2)/3
2840 reflections(Δ/σ)max = 0.001
185 parametersΔρmax = 0.22 e Å−3
1 restraintΔρmin = −0.38 e Å−3
Crystal data top
C14H12ClNO3SV = 2801.8 (4) Å3
Mr = 309.76Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.719 (1) ŵ = 0.43 mm−1
b = 9.6781 (9) ÅT = 299 K
c = 21.102 (2) Å0.34 × 0.24 × 0.14 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2840 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1902 reflections with I > 2σ(I)
Tmin = 0.868, Tmax = 0.943Rint = 0.018
6658 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123Δρmax = 0.22 e Å−3
S = 1.02Δρmin = −0.38 e Å−3
2840 reflectionsAbsolute structure: ?
185 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

Experimental. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.01547 (17)0.2340 (2)0.44377 (11)0.0399 (6)
C2−0.0141 (2)0.1166 (3)0.41247 (14)0.0546 (7)
H20.02280.03620.41510.066*
C3−0.0983 (2)0.1187 (3)0.37717 (15)0.0594 (8)
H3−0.11870.03990.35570.071*
C4−0.15186 (19)0.2375 (3)0.37395 (13)0.0498 (7)
C5−0.1248 (2)0.3538 (3)0.40560 (15)0.0647 (9)
H5−0.16300.43310.40370.078*
C6−0.0399 (2)0.3523 (3)0.44044 (14)0.0601 (8)
H6−0.02000.43150.46180.072*
C70.23281 (17)0.3764 (2)0.40867 (12)0.0396 (6)
C80.31666 (17)0.3739 (2)0.36415 (12)0.0389 (6)
C90.31635 (19)0.4681 (3)0.31449 (13)0.0477 (7)
H90.26530.53070.31050.057*
C100.3915 (2)0.4689 (3)0.27110 (13)0.0543 (7)
H100.38950.53110.23750.065*
C110.47023 (19)0.3788 (3)0.27635 (13)0.0485 (7)
C120.47077 (19)0.2883 (3)0.32716 (14)0.0505 (7)
H120.52360.22910.33250.061*
C130.39507 (17)0.2836 (2)0.37016 (13)0.0452 (6)
H130.39650.22000.40320.054*
C140.5521 (2)0.3835 (4)0.22922 (14)0.0688 (9)
H14A0.61000.41700.24960.083*
H14B0.53490.44410.19500.083*
H14C0.56360.29230.21290.083*
N10.21363 (15)0.25385 (19)0.43927 (10)0.0426 (5)
H1N0.2442 (17)0.1798 (17)0.4294 (12)0.051*
O10.11997 (14)0.3386 (2)0.53406 (9)0.0630 (6)
O20.13812 (14)0.0896 (2)0.51002 (10)0.0652 (6)
O30.18237 (12)0.47861 (16)0.41670 (9)0.0508 (5)
Cl1−0.25653 (6)0.24046 (10)0.32788 (4)0.0778 (3)
S10.12257 (5)0.22796 (7)0.48971 (3)0.0467 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (12)0.0428 (13)0.0427 (13)−0.0006 (11)0.0059 (11)0.0013 (11)
C20.0459 (16)0.0424 (15)0.076 (2)0.0001 (12)0.0084 (15)−0.0008 (14)
C30.0526 (17)0.0527 (17)0.073 (2)−0.0120 (14)0.0018 (16)−0.0128 (15)
C40.0354 (13)0.0656 (19)0.0484 (15)−0.0080 (13)0.0021 (12)−0.0025 (14)
C50.0543 (18)0.0612 (19)0.079 (2)0.0170 (15)−0.0166 (17)−0.0161 (16)
C60.0596 (19)0.0487 (16)0.072 (2)0.0117 (14)−0.0163 (16)−0.0231 (15)
C70.0333 (12)0.0321 (12)0.0533 (15)−0.0024 (10)−0.0082 (11)−0.0003 (11)
C80.0307 (12)0.0315 (12)0.0546 (15)−0.0052 (10)−0.0063 (12)0.0027 (11)
C90.0404 (14)0.0418 (14)0.0610 (17)0.0024 (11)−0.0080 (14)0.0111 (13)
C100.0506 (16)0.0581 (17)0.0543 (17)−0.0041 (14)−0.0065 (14)0.0172 (14)
C110.0400 (14)0.0534 (16)0.0521 (16)−0.0047 (12)−0.0018 (13)0.0007 (13)
C120.0374 (13)0.0434 (14)0.0708 (18)0.0016 (11)0.0027 (13)0.0051 (14)
C130.0381 (14)0.0341 (13)0.0634 (17)−0.0007 (11)−0.0008 (12)0.0102 (12)
C140.0534 (17)0.092 (2)0.061 (2)−0.0003 (17)0.0042 (16)0.0058 (17)
N10.0375 (11)0.0293 (10)0.0609 (14)0.0022 (9)0.0068 (10)0.0059 (10)
O10.0613 (13)0.0790 (14)0.0488 (11)0.0100 (11)−0.0077 (10)−0.0115 (10)
O20.0522 (12)0.0624 (12)0.0811 (14)0.0026 (9)0.0055 (11)0.0353 (11)
O30.0428 (10)0.0329 (9)0.0768 (13)0.0056 (8)0.0008 (10)0.0044 (9)
Cl10.0498 (4)0.1078 (7)0.0758 (6)−0.0148 (4)−0.0150 (4)0.0022 (5)
S10.0408 (4)0.0505 (4)0.0489 (4)0.0031 (3)0.0019 (3)0.0095 (3)
Geometric parameters (Å, °) top
C1—C21.375 (3)C9—C101.379 (4)
C1—C61.376 (3)C9—H90.9300
C1—S11.761 (3)C10—C111.393 (4)
C2—C31.375 (4)C10—H100.9300
C2—H20.9300C11—C121.384 (4)
C3—C41.366 (4)C11—C141.500 (4)
C3—H30.9300C12—C131.380 (4)
C4—C51.360 (4)C12—H120.9300
C4—Cl11.734 (3)C13—H130.9300
C5—C61.377 (4)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O31.219 (3)N1—S11.660 (2)
C7—N11.376 (3)N1—H1N0.856 (10)
C7—C81.485 (3)O1—S11.423 (2)
C8—C91.389 (3)O2—S11.4224 (19)
C8—C131.392 (3)
C2—C1—C6120.0 (2)C9—C10—C11121.6 (3)
C2—C1—S1118.9 (2)C9—C10—H10119.2
C6—C1—S1121.1 (2)C11—C10—H10119.2
C1—C2—C3119.7 (3)C12—C11—C10117.5 (3)
C1—C2—H2120.1C12—C11—C14121.9 (3)
C3—C2—H2120.1C10—C11—C14120.6 (3)
C4—C3—C2119.4 (3)C13—C12—C11121.8 (2)
C4—C3—H3120.3C13—C12—H12119.1
C2—C3—H3120.3C11—C12—H12119.1
C5—C4—C3121.7 (3)C12—C13—C8120.1 (2)
C5—C4—Cl1119.2 (2)C12—C13—H13120.0
C3—C4—Cl1119.1 (2)C8—C13—H13120.0
C4—C5—C6119.0 (3)C11—C14—H14A109.5
C4—C5—H5120.5C11—C14—H14B109.5
C6—C5—H5120.5H14A—C14—H14B109.5
C1—C6—C5120.2 (3)C11—C14—H14C109.5
C1—C6—H6119.9H14A—C14—H14C109.5
C5—C6—H6119.9H14B—C14—H14C109.5
O3—C7—N1121.7 (2)C7—N1—S1125.09 (17)
O3—C7—C8122.7 (2)C7—N1—H1N121.0 (18)
N1—C7—C8115.5 (2)S1—N1—H1N113.4 (18)
C9—C8—C13118.9 (2)O2—S1—O1120.95 (13)
C9—C8—C7117.7 (2)O2—S1—N1102.86 (11)
C13—C8—C7123.5 (2)O1—S1—N1109.09 (12)
C10—C9—C8120.2 (2)O2—S1—C1108.79 (12)
C10—C9—H9119.9O1—S1—C1108.44 (12)
C8—C9—H9119.9N1—S1—C1105.66 (11)
C6—C1—C2—C30.9 (4)C9—C10—C11—C14−178.8 (3)
S1—C1—C2—C3179.0 (2)C10—C11—C12—C132.0 (4)
C1—C2—C3—C4−0.3 (4)C14—C11—C12—C13−179.5 (3)
C2—C3—C4—C5−1.0 (5)C11—C12—C13—C8−1.8 (4)
C2—C3—C4—Cl1178.5 (2)C9—C8—C13—C12−0.1 (4)
C3—C4—C5—C61.6 (5)C7—C8—C13—C12−179.4 (2)
Cl1—C4—C5—C6−177.9 (2)O3—C7—N1—S10.0 (4)
C2—C1—C6—C5−0.2 (4)C8—C7—N1—S1−178.24 (17)
S1—C1—C6—C5−178.3 (2)C7—N1—S1—O2−177.0 (2)
C4—C5—C6—C1−1.0 (5)C7—N1—S1—O1−47.4 (2)
O3—C7—C8—C9−24.1 (4)C7—N1—S1—C169.0 (2)
N1—C7—C8—C9154.1 (2)C2—C1—S1—O2−26.1 (2)
O3—C7—C8—C13155.3 (3)C6—C1—S1—O2152.0 (2)
N1—C7—C8—C13−26.5 (3)C2—C1—S1—O1−159.4 (2)
C13—C8—C9—C101.7 (4)C6—C1—S1—O118.6 (3)
C7—C8—C9—C10−178.9 (2)C2—C1—S1—N183.7 (2)
C8—C9—C10—C11−1.5 (4)C6—C1—S1—N1−98.2 (2)
C9—C10—C11—C12−0.4 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.86 (1)2.21 (1)3.059 (3)172 (2)
Symmetry codes: (i) −x+1/2, y−1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.86 (1)2.21 (1)3.059 (3)172 (2)
Symmetry codes: (i) −x+1/2, y−1/2, z.
Acknowledgements top

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

references
References top

Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.

Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o327.

Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o766.

Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010c). Acta Cryst. E66, o1253.