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ISSN: 2056-9890

2-Chloro-N-(2-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

(Received 29 April 2010; accepted 30 April 2010; online 8 May 2010)

In the title compound, C14H12ClNO3S, the N—H bond is anti­periplanar to the C=O bond. The dihedral angle between the two aromatic rings is 78.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) 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 sulfonamides and for related structures, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.], 2010a[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010a). Acta Cryst. E66, o794.],b[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010b). Acta Cryst. E66, o326.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO3S

  • Mr = 309.76

  • Monoclinic, P 21 /n

  • a = 6.6086 (5) Å

  • b = 10.9621 (9) Å

  • c = 20.080 (2) Å

  • β = 95.586 (8)°

  • V = 1447.8 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 299 K

  • 0.34 × 0.32 × 0.28 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.872, Tmax = 0.893

  • 5395 measured reflections

  • 2917 independent reflections

  • 2592 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.07

  • 2917 reflections

  • 186 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2i 0.84 (2) 2.11 (2) 2.937 (2) 172 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the present work, 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, 2010a,b), the structure of 2-chloro-N-(2-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 N-(2-chlorobenzoyl)2-chlorobenzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010a).

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

The molecules are twisted at the S atom with the torsional angle of -64.0 (2)°, compared to those of 66.5 (2)° in (II), -66.9 (3)° in (III), and 66.7 (2)° in (IV).

The dihedral angles between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.4 (1)°, compared to the values of 86.9 (1)° in (II), 86.5(0.1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 78.7 (1)°, compared to the values of 76.9 (1)° in (II), of 80.3(0.1) in (III), 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (III) and 73.3 (1)° in (IV).

The packing of molecules linked by N—H···O(S) 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 substitutions on the crystal structures of N-aryl sulfonamides and for related structures, see: Gowda et al. (2009, 2010a,b).

Experimental top

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

Refinement top

The H atom of the NH group was located in a difference map and its coordinates were refined with a distance restraint of N—H = 0.86 (2) %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.

Structure description top

In the present work, 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, 2010a,b), the structure of 2-chloro-N-(2-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 N-(2-chlorobenzoyl)2-chlorobenzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010a).

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

The molecules are twisted at the S atom with the torsional angle of -64.0 (2)°, compared to those of 66.5 (2)° in (II), -66.9 (3)° in (III), and 66.7 (2)° in (IV).

The dihedral angles between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.4 (1)°, compared to the values of 86.9 (1)° in (II), 86.5(0.1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 78.7 (1)°, compared to the values of 76.9 (1)° in (II), of 80.3(0.1) in (III), 69.8 (1)° (molecule 1) and 89.8 (1)° (molecule 2) in (III) and 73.3 (1)° in (IV).

The packing of molecules linked by N—H···O(S) 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 sulfonamides and for related structures, see: Gowda et al. (2009, 2010a,b).

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.
2-Chloro-N-(2-methylbenzoyl)benzenesulfonamide top
Crystal data top
C14H12ClNO3SF(000) = 640
Mr = 309.76Dx = 1.421 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3866 reflections
a = 6.6086 (5) Åθ = 2.7–27.8°
b = 10.9621 (9) ŵ = 0.41 mm1
c = 20.080 (2) ÅT = 299 K
β = 95.586 (8)°Prism, colourless
V = 1447.8 (2) Å30.34 × 0.32 × 0.28 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2917 independent reflections
Radiation source: fine-focus sealed tube2592 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 78
Tmin = 0.872, Tmax = 0.893k = 137
5395 measured reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.7805P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2917 reflectionsΔρmax = 0.31 e Å3
186 parametersΔρmin = 0.33 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.146 (5)
Crystal data top
C14H12ClNO3SV = 1447.8 (2) Å3
Mr = 309.76Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.6086 (5) ŵ = 0.41 mm1
b = 10.9621 (9) ÅT = 299 K
c = 20.080 (2) Å0.34 × 0.32 × 0.28 mm
β = 95.586 (8)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2917 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2592 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.893Rint = 0.017
5395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.31 e Å3
2917 reflectionsΔρmin = 0.33 e Å3
186 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2188 (3)0.22154 (17)0.45434 (9)0.0389 (4)
C20.3529 (3)0.2921 (2)0.42162 (11)0.0504 (5)
C30.5045 (4)0.2357 (3)0.38928 (13)0.0717 (8)
H30.59400.28210.36670.086*
C40.5208 (4)0.1097 (3)0.39104 (14)0.0771 (9)
H40.62370.07190.37020.092*
C50.3890 (4)0.0403 (3)0.42274 (13)0.0658 (7)
H50.40050.04430.42280.079*
C60.2392 (4)0.0956 (2)0.45452 (10)0.0502 (5)
H60.15000.04800.47650.060*
C70.2598 (3)0.30250 (17)0.61222 (9)0.0392 (4)
C80.3281 (3)0.38164 (17)0.67032 (9)0.0389 (4)
C90.5185 (3)0.3631 (2)0.70605 (11)0.0492 (5)
C100.5679 (4)0.4362 (3)0.76164 (13)0.0661 (7)
H100.69370.42570.78600.079*
C110.4385 (4)0.5231 (3)0.78199 (13)0.0680 (7)
H110.47590.56930.82010.082*
C120.2534 (4)0.5422 (2)0.74615 (12)0.0608 (6)
H120.16600.60200.75940.073*
C130.1982 (3)0.4717 (2)0.69029 (10)0.0472 (5)
H130.07310.48450.66580.057*
C140.6730 (4)0.2723 (3)0.68618 (15)0.0696 (7)
H14A0.68140.27700.63880.083*
H14B0.63250.19150.69770.083*
H14C0.80340.29050.70940.083*
N10.1386 (3)0.36014 (14)0.56089 (8)0.0412 (4)
H1N0.135 (3)0.4361 (15)0.5574 (11)0.049*
O10.0894 (2)0.18713 (14)0.52207 (8)0.0559 (4)
O20.0831 (2)0.37563 (12)0.45683 (8)0.0497 (4)
O30.3005 (3)0.19555 (13)0.60869 (7)0.0554 (4)
Cl10.34073 (12)0.45035 (6)0.42249 (4)0.0807 (3)
S10.02324 (7)0.28443 (4)0.49721 (2)0.03857 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0448 (10)0.0355 (10)0.0351 (9)0.0007 (8)0.0027 (7)0.0024 (7)
C20.0472 (11)0.0577 (13)0.0447 (11)0.0085 (10)0.0030 (9)0.0012 (9)
C30.0462 (12)0.117 (3)0.0523 (13)0.0120 (14)0.0068 (10)0.0090 (15)
C40.0600 (15)0.108 (2)0.0607 (15)0.0241 (16)0.0054 (12)0.0369 (16)
C50.0772 (17)0.0629 (16)0.0551 (14)0.0211 (13)0.0052 (12)0.0178 (12)
C60.0670 (13)0.0384 (11)0.0440 (11)0.0063 (10)0.0001 (9)0.0051 (9)
C70.0477 (10)0.0337 (9)0.0366 (9)0.0017 (8)0.0067 (8)0.0037 (7)
C80.0473 (10)0.0349 (9)0.0351 (9)0.0035 (8)0.0076 (8)0.0031 (7)
C90.0507 (11)0.0501 (12)0.0465 (11)0.0030 (9)0.0038 (9)0.0045 (9)
C100.0616 (14)0.0768 (18)0.0574 (14)0.0082 (13)0.0074 (11)0.0048 (13)
C110.0824 (18)0.0715 (17)0.0497 (13)0.0146 (14)0.0038 (12)0.0161 (12)
C120.0743 (15)0.0569 (14)0.0534 (13)0.0010 (12)0.0185 (11)0.0140 (11)
C130.0527 (11)0.0465 (11)0.0432 (10)0.0024 (9)0.0085 (9)0.0018 (9)
C140.0565 (14)0.0680 (17)0.0833 (18)0.0118 (12)0.0019 (13)0.0033 (14)
N10.0570 (10)0.0242 (7)0.0411 (8)0.0016 (7)0.0015 (7)0.0002 (6)
O10.0591 (9)0.0400 (8)0.0701 (10)0.0135 (7)0.0146 (8)0.0011 (7)
O20.0509 (8)0.0349 (7)0.0597 (9)0.0040 (6)0.0124 (7)0.0026 (6)
O30.0846 (11)0.0320 (7)0.0483 (8)0.0118 (7)0.0006 (7)0.0017 (6)
Cl10.0810 (5)0.0573 (4)0.1049 (6)0.0258 (3)0.0148 (4)0.0216 (4)
S10.0428 (3)0.0266 (3)0.0456 (3)0.00243 (18)0.00085 (19)0.00064 (18)
Geometric parameters (Å, º) top
C1—C61.387 (3)C9—C101.387 (3)
C1—C21.389 (3)C9—C141.507 (3)
C1—S11.761 (2)C10—C111.369 (4)
C2—C31.391 (4)C10—H100.9300
C2—Cl11.737 (3)C11—C121.373 (4)
C3—C41.386 (4)C11—H110.9300
C3—H30.9300C12—C131.382 (3)
C4—C51.361 (4)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.370 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O31.206 (2)N1—S11.6478 (17)
C7—N11.394 (2)N1—H1N0.836 (16)
C7—C81.488 (3)O1—S11.4188 (15)
C8—C131.393 (3)O2—S11.4283 (14)
C8—C91.401 (3)
C6—C1—C2119.3 (2)C11—C10—C9122.5 (2)
C6—C1—S1117.65 (17)C11—C10—H10118.7
C2—C1—S1123.06 (16)C9—C10—H10118.7
C1—C2—C3119.7 (2)C10—C11—C12120.0 (2)
C1—C2—Cl1121.28 (18)C10—C11—H11120.0
C3—C2—Cl1119.0 (2)C12—C11—H11120.0
C4—C3—C2119.2 (3)C11—C12—C13119.5 (2)
C4—C3—H3120.4C11—C12—H12120.3
C2—C3—H3120.4C13—C12—H12120.3
C5—C4—C3121.2 (2)C12—C13—C8120.6 (2)
C5—C4—H4119.4C12—C13—H13119.7
C3—C4—H4119.4C8—C13—H13119.7
C4—C5—C6119.7 (3)C9—C14—H14A109.5
C4—C5—H5120.2C9—C14—H14B109.5
C6—C5—H5120.2H14A—C14—H14B109.5
C5—C6—C1120.9 (2)C9—C14—H14C109.5
C5—C6—H6119.5H14A—C14—H14C109.5
C1—C6—H6119.5H14B—C14—H14C109.5
O3—C7—N1120.83 (18)C7—N1—S1122.33 (13)
O3—C7—C8124.07 (18)C7—N1—H1N121.6 (16)
N1—C7—C8115.09 (16)S1—N1—H1N115.4 (16)
C13—C8—C9120.23 (19)O1—S1—O2118.67 (10)
C13—C8—C7119.36 (18)O1—S1—N1108.94 (9)
C9—C8—C7120.38 (18)O2—S1—N1104.66 (8)
C10—C9—C8117.2 (2)O1—S1—C1108.22 (9)
C10—C9—C14118.8 (2)O2—S1—C1109.90 (9)
C8—C9—C14123.9 (2)N1—S1—C1105.69 (9)
C6—C1—C2—C30.4 (3)C8—C9—C10—C110.2 (4)
S1—C1—C2—C3179.48 (17)C14—C9—C10—C11178.2 (3)
C6—C1—C2—Cl1177.48 (16)C9—C10—C11—C121.3 (4)
S1—C1—C2—Cl11.6 (2)C10—C11—C12—C131.0 (4)
C1—C2—C3—C40.8 (3)C11—C12—C13—C80.2 (4)
Cl1—C2—C3—C4177.1 (2)C9—C8—C13—C121.2 (3)
C2—C3—C4—C51.2 (4)C7—C8—C13—C12176.6 (2)
C3—C4—C5—C61.1 (4)O3—C7—N1—S17.1 (3)
C4—C5—C6—C10.6 (4)C8—C7—N1—S1171.69 (14)
C2—C1—C6—C50.2 (3)C7—N1—S1—O152.08 (18)
S1—C1—C6—C5179.40 (17)C7—N1—S1—O2179.96 (16)
O3—C7—C8—C13143.2 (2)C7—N1—S1—C164.00 (18)
N1—C7—C8—C1335.5 (3)C6—C1—S1—O13.36 (19)
O3—C7—C8—C934.6 (3)C2—C1—S1—O1177.51 (16)
N1—C7—C8—C9146.66 (19)C6—C1—S1—O2134.38 (16)
C13—C8—C9—C101.0 (3)C2—C1—S1—O246.49 (18)
C7—C8—C9—C10176.8 (2)C6—C1—S1—N1113.21 (16)
C13—C8—C9—C14176.9 (2)C2—C1—S1—N165.91 (18)
C7—C8—C9—C145.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.84 (2)2.11 (2)2.937 (2)172 (2)
Symmetry code: (i) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC14H12ClNO3S
Mr309.76
Crystal system, space groupMonoclinic, P21/n
Temperature (K)299
a, b, c (Å)6.6086 (5), 10.9621 (9), 20.080 (2)
β (°) 95.586 (8)
V3)1447.8 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.41
Crystal size (mm)0.34 × 0.32 × 0.28
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.872, 0.893
No. of measured, independent and
observed [I > 2σ(I)] reflections
5395, 2917, 2592
Rint0.017
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.110, 1.07
No. of reflections2917
No. of parameters186
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.33

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.836 (16)2.107 (17)2.937 (2)172 (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

First citationGowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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