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Acta Cryst. (2010). E66, o1467    [ doi:10.1107/S1600536810019057 ]

4-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide

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

Abstract top

In the structure of the title compound, C13H9Cl2NO3S, 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 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO2-NH-C-O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, molecules are linked by pairs of 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., 2010; Suchetan et al., 2010a,b,c), the structure of N-(2-chlorobenzoyl)-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-(2-chlorobenzoyl)-benzenesulfonamide (II) (Gowda et al., 2010), N-(benzoyl)-4-chlorobenzenesulfonamide (III) (Suchetan et al., 2010a), N-(2-chlorobenzoyl)-2-chlorobenzenesulfonamide (IV) (Suchetan et al., 2010b) and N-(4-chlorobenzoyl)-4- chlorobenzenesulfonamide (V) (Suchetan et al., 2010c).

Further, the conformation of the C=O bond in the C—SO2—NH—C(O) segment of (I) is syn to the ortho-Cl in the benzoyl ring, similar to that observed in (II) and (IV).

The molecules are twisted at the S atom with the torsional angle of 65.7 (2)°, compared to those of -59.0 (2)° (molecule 1) and -67.3 (2)° (molecule 2) in (II), -70.0 (2)°, 61.3 (2)° in the two independent molecules of (III), 66.5 (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 88.5 (1)°, compared to the values of 87.3 (1)° (molecule 1) and 73.3 (1)° (molecule 2) in (II), 72.0 (1)° & 77.3 (1)° in the two molecules of (III), 86.9 (1)° in (IV) and 79.0 (1)° in (V).

Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°, compared to the values of 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (II), 62.8 (1)° (molecule 1) and 78.6 (1)° (molecule 2) of (III), 76.9 (1)° in (IV) and 85.6 (1)° in (V)

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

Related literature top

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

Experimental top

The title compound was prepared by refluxing a mixture of 2-chlorobenzoic 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.

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.

Refinement top

The H atoms of the NH groups were 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 = 0.93 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-(2-chlorobenzoyl)benzenesulfonamide top
Crystal data top
C13H9Cl2NO3SZ = 2
Mr = 330.17F(000) = 336
Triclinic, P1Dx = 1.577 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3882 (9) ÅCell parameters from 2339 reflections
b = 10.311 (1) Åθ = 2.5–27.8°
c = 11.171 (1) ŵ = 0.62 mm−1
α = 79.01 (1)°T = 299 K
β = 74.47 (1)°Prism, colourless
γ = 84.76 (1)°0.24 × 0.20 × 0.14 mm
V = 695.32 (13) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2825 independent reflections
Radiation source: fine-focus sealed tube2378 reflections with I > 2σ(I)
graphiteRint = 0.016
ω and φ scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −7→7
Tmin = 0.865, Tmax = 0.918k = −12→11
4417 measured reflectionsl = −13→13
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1863P]
where P = (Fo2 + 2Fc2)/3
2825 reflections(Δ/σ)max = 0.022
184 parametersΔρmax = 0.25 e Å−3
1 restraintΔρmin = −0.52 e Å−3
Crystal data top
C13H9Cl2NO3Sγ = 84.76 (1)°
Mr = 330.17V = 695.32 (13) Å3
Triclinic, P1Z = 2
a = 6.3882 (9) ÅMo Kα radiation
b = 10.311 (1) ŵ = 0.62 mm−1
c = 11.171 (1) ÅT = 299 K
α = 79.01 (1)°0.24 × 0.20 × 0.14 mm
β = 74.47 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector		2825 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		2378 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.918Rint = 0.016
4417 measured reflectionsθmax = 26.4°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107Δρmax = 0.25 e Å−3
S = 1.06Δρmin = −0.52 e Å−3
2825 reflectionsAbsolute structure: ?
184 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3004 (3)0.27841 (17)0.07988 (17)0.0364 (4)
C20.1714 (3)0.39202 (19)0.0968 (2)0.0464 (5)
H20.04370.40590.07030.056*
C30.2338 (4)0.4844 (2)0.1532 (2)0.0561 (6)
H30.15100.56240.16340.067*
C40.4198 (4)0.4596 (2)0.1942 (2)0.0520 (5)
C50.5482 (4)0.3465 (2)0.1791 (2)0.0543 (5)
H50.67300.33170.20850.065*
C60.4895 (3)0.2553 (2)0.1198 (2)0.0478 (5)
H60.57600.17910.10680.057*
C70.0089 (3)0.02215 (18)0.22952 (18)0.0384 (4)
C80.0163 (3)−0.09961 (18)0.32606 (17)0.0396 (4)
C90.1632 (3)−0.1155 (2)0.39978 (18)0.0451 (4)
C100.1579 (5)−0.2246 (3)0.4941 (2)0.0641 (7)
H100.2565−0.23470.54360.077*
C110.0073 (6)−0.3171 (3)0.5141 (2)0.0757 (8)
H110.0043−0.39080.57710.091*
C12−0.1402 (5)−0.3025 (3)0.4422 (3)0.0730 (7)
H12−0.2424−0.36630.45680.088*
C13−0.1370 (4)−0.1940 (2)0.3487 (2)0.0554 (5)
H13−0.2378−0.18400.30070.066*
Cl10.34983 (10)0.00381 (7)0.37663 (6)0.0664 (2)
Cl20.49683 (16)0.57327 (7)0.26873 (8)0.0938 (3)
N10.1748 (3)0.02815 (15)0.12059 (15)0.0398 (4)
H1N0.276 (3)−0.0255 (19)0.114 (2)0.048*
O10.0294 (3)0.20637 (15)−0.02823 (14)0.0550 (4)
O20.4074 (3)0.11865 (14)−0.08329 (13)0.0537 (4)
O3−0.1307 (2)0.10807 (16)0.24443 (16)0.0602 (4)
S10.22277 (8)0.15972 (4)0.00846 (4)0.04047 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0364 (9)0.0325 (8)0.0360 (9)−0.0001 (7)−0.0058 (7)−0.0008 (7)
C20.0448 (11)0.0390 (10)0.0503 (11)0.0069 (8)−0.0122 (9)0.0006 (8)
C30.0695 (14)0.0344 (10)0.0568 (13)0.0062 (9)−0.0075 (11)−0.0055 (9)
C40.0665 (14)0.0424 (11)0.0432 (11)−0.0177 (9)−0.0044 (10)−0.0045 (8)
C50.0468 (11)0.0561 (13)0.0610 (13)−0.0108 (9)−0.0159 (10)−0.0051 (10)
C60.0382 (10)0.0431 (10)0.0617 (13)0.0040 (8)−0.0140 (9)−0.0091 (9)
C70.0365 (9)0.0413 (9)0.0406 (9)−0.0023 (7)−0.0146 (7)−0.0076 (7)
C80.0430 (10)0.0399 (9)0.0342 (9)0.0004 (7)−0.0076 (7)−0.0064 (7)
C90.0464 (10)0.0529 (11)0.0364 (10)0.0068 (8)−0.0111 (8)−0.0120 (8)
C100.0786 (16)0.0707 (15)0.0399 (11)0.0199 (13)−0.0188 (11)−0.0076 (10)
C110.112 (2)0.0556 (14)0.0457 (13)0.0047 (14)−0.0087 (14)0.0059 (11)
C120.095 (2)0.0539 (14)0.0628 (16)−0.0230 (13)−0.0095 (14)0.0015 (12)
C130.0615 (13)0.0548 (12)0.0500 (12)−0.0148 (10)−0.0127 (10)−0.0059 (10)
Cl10.0571 (4)0.0895 (4)0.0633 (4)−0.0126 (3)−0.0273 (3)−0.0178 (3)
Cl20.1363 (7)0.0706 (5)0.0834 (5)−0.0386 (4)−0.0236 (5)−0.0259 (4)
N10.0441 (9)0.0340 (8)0.0394 (8)0.0013 (6)−0.0095 (7)−0.0049 (6)
O10.0577 (9)0.0586 (9)0.0546 (9)0.0005 (7)−0.0303 (7)−0.0030 (7)
O20.0656 (9)0.0503 (8)0.0367 (7)0.0079 (7)−0.0037 (6)−0.0050 (6)
O30.0483 (8)0.0617 (9)0.0603 (10)0.0152 (7)−0.0092 (7)−0.0008 (7)
S10.0464 (3)0.0387 (3)0.0356 (3)0.00192 (18)−0.01273 (19)−0.00320 (18)
Geometric parameters (Å, °) top
C1—C61.382 (3)C8—C131.385 (3)
C1—C21.383 (3)C8—C91.386 (3)
C1—S11.7537 (19)C9—C101.382 (3)
C2—C31.377 (3)C9—Cl11.727 (2)
C2—H20.9300C10—C111.363 (4)
C3—C41.370 (3)C10—H100.9300
C3—H30.9300C11—C121.375 (4)
C4—C51.374 (3)C11—H110.9300
C4—Cl21.733 (2)C12—C131.375 (3)
C5—C61.379 (3)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300N1—S11.6510 (16)
C7—O31.200 (2)N1—H1N0.810 (15)
C7—N11.379 (3)O1—S11.4185 (15)
C7—C81.497 (3)O2—S11.4311 (15)
C6—C1—C2121.20 (18)C10—C9—C8120.5 (2)
C6—C1—S1118.92 (14)C10—C9—Cl1119.64 (18)
C2—C1—S1119.87 (15)C8—C9—Cl1119.82 (16)
C3—C2—C1119.35 (19)C11—C10—C9119.6 (2)
C3—C2—H2120.3C11—C10—H10120.2
C1—C2—H2120.3C9—C10—H10120.2
C4—C3—C2119.03 (19)C10—C11—C12120.7 (2)
C4—C3—H3120.5C10—C11—H11119.7
C2—C3—H3120.5C12—C11—H11119.7
C3—C4—C5122.2 (2)C13—C12—C11120.2 (2)
C3—C4—Cl2119.51 (17)C13—C12—H12119.9
C5—C4—Cl2118.31 (18)C11—C12—H12119.9
C4—C5—C6119.0 (2)C12—C13—C8120.0 (2)
C4—C5—H5120.5C12—C13—H13120.0
C6—C5—H5120.5C8—C13—H13120.0
C5—C6—C1119.17 (18)C7—N1—S1124.25 (13)
C5—C6—H6120.4C7—N1—H1N121.9 (16)
C1—C6—H6120.4S1—N1—H1N112.1 (16)
O3—C7—N1122.05 (18)O1—S1—O2119.26 (9)
O3—C7—C8123.12 (18)O1—S1—N1110.18 (9)
N1—C7—C8114.82 (15)O2—S1—N1103.74 (8)
C13—C8—C9119.07 (19)O1—S1—C1108.96 (9)
C13—C8—C7119.35 (17)O2—S1—C1109.21 (9)
C9—C8—C7121.40 (17)N1—S1—C1104.43 (8)
C6—C1—C2—C30.7 (3)C8—C9—C10—C110.2 (3)
S1—C1—C2—C3179.87 (16)Cl1—C9—C10—C11178.50 (19)
C1—C2—C3—C4−1.7 (3)C9—C10—C11—C12−0.5 (4)
C2—C3—C4—C51.0 (3)C10—C11—C12—C130.1 (4)
C2—C3—C4—Cl2−178.50 (16)C11—C12—C13—C80.6 (4)
C3—C4—C5—C60.6 (3)C9—C8—C13—C12−0.9 (3)
Cl2—C4—C5—C6−179.85 (17)C7—C8—C13—C12−176.2 (2)
C4—C5—C6—C1−1.6 (3)O3—C7—N1—S19.1 (3)
C2—C1—C6—C50.9 (3)C8—C7—N1—S1−171.37 (13)
S1—C1—C6—C5−178.23 (16)C7—N1—S1—O1−51.19 (18)
O3—C7—C8—C1370.4 (3)C7—N1—S1—O2−179.94 (15)
N1—C7—C8—C13−109.1 (2)C7—N1—S1—C165.68 (17)
O3—C7—C8—C9−104.8 (2)C6—C1—S1—O1−178.06 (15)
N1—C7—C8—C975.7 (2)C2—C1—S1—O12.78 (18)
C13—C8—C9—C100.4 (3)C6—C1—S1—O2−46.22 (18)
C7—C8—C9—C10175.66 (18)C2—C1—S1—O2134.61 (15)
C13—C8—C9—Cl1−177.81 (16)C6—C1—S1—N164.23 (17)
C7—C8—C9—Cl1−2.6 (3)C2—C1—S1—N1−114.93 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.81 (2)2.13 (2)2.914 (2)164 (2)
Symmetry codes: (i) −x+1, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.81 (2)2.13 (2)2.914 (2)164 (2)
Symmetry codes: (i) −x+1, −y, −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. (2010). Acta Cryst. E66, o326.

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, o766.

Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1040.

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