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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1292.
Published online 2010 May 8. doi:  10.1107/S1600536810016235
PMCID: PMC2979524

2-Chloro-N-(3-methyl­benzo­yl)benzene­sulfonamide

Abstract

In the title compound, C14H12ClNO3S, the N—H bond is in an anti­periplanar conformation to the C=O bond. The dihedral angle between the two aromatic rings is 74.7 (1)°. The crystal structure features inversion-related dimers linked by N—H(...)O 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 [triangle], 2010 [triangle]); Suchetan et al. (2010 [triangle]).

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Object name is e-66-o1292-scheme1.jpg

Experimental

Crystal data

  • C14H12ClNO3S
  • M r = 309.76
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1292-efi1.jpg
  • a = 12.4487 (8) Å
  • b = 13.4619 (8) Å
  • c = 17.455 (1) Å
  • V = 2925.2 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 299 K
  • 0.30 × 0.30 × 0.20 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.887, T max = 0.923
  • 7216 measured reflections
  • 2955 independent reflections
  • 2422 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.095
  • S = 1.04
  • 2955 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016235/bt5261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016235/bt5261Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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, 2010; Suchetan et al., 2010)), in the present work, the structure of 2-chloro-N-(3-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 2-chloro-N-(2-methylbenzoyl)benzenesulfonamide (II) (Suchetan et al., 2010), N-(benzoyl)benzenesulfonamide (III) (Gowda et al., 2009), and N-(benzoyl)2-chlorobenzenesulfonamide (IV) (Gowda et al., 2010).

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

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

The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.4 (1)°, compared to the values of 84.8 (1)° in (II), 86.5 (1) in (III) and 87.3 (1)° in (IV). Furthermore, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 74.7 (1)°, compared to the values of 78.7 (1)° in (II), of 80.3 (1) in (III) and 73.3 (1)° in (IV).

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

Experimental

The title compound was prepared by refluxing a mixture of 3-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

The H atom of the NH group was located in a difference map and refined with a distance restraint of N—H = 0.86 (2)Å. The other H atoms were positioned with idealized geometry and refined 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.

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H12ClNO3SF(000) = 1280
Mr = 309.76Dx = 1.407 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5313 reflections
a = 12.4487 (8) Åθ = 2.8–27.7°
b = 13.4619 (8) ŵ = 0.41 mm1
c = 17.455 (1) ÅT = 299 K
V = 2925.2 (3) Å3Prism, colourless
Z = 80.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2955 independent reflections
Radiation source: fine-focus sealed tube2422 reflections with I > 2σ(I)
graphiteRint = 0.014
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −15→11
Tmin = 0.887, Tmax = 0.923k = −16→9
7216 measured reflectionsl = −12→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095w = 1/[σ2(Fo2) + (0.0429P)2 + 1.518P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2955 reflectionsΔρmax = 0.20 e Å3
186 parametersΔρmin = −0.28 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: 0.0265 (11)

Special details

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)

xyzUiso*/Ueq
C1−0.00620 (14)0.25666 (13)0.42487 (10)0.0366 (4)
C2−0.09360 (15)0.24307 (16)0.47300 (11)0.0452 (5)
C3−0.1408 (2)0.15010 (19)0.47939 (15)0.0634 (6)
H3−0.19920.14080.51180.076*
C4−0.1008 (2)0.07177 (18)0.43768 (16)0.0688 (7)
H4−0.13230.00950.44230.083*
C5−0.0152 (2)0.08419 (16)0.38944 (15)0.0627 (6)
H50.01090.03070.36140.075*
C60.03249 (18)0.17676 (14)0.38256 (12)0.0482 (5)
H60.09040.18550.34960.058*
C7−0.06413 (15)0.45303 (13)0.31212 (10)0.0381 (4)
C8−0.13360 (15)0.53961 (13)0.29432 (10)0.0373 (4)
C9−0.11657 (16)0.63233 (13)0.32775 (11)0.0404 (4)
H9−0.05930.64100.36130.049*
C10−0.18376 (18)0.71203 (15)0.31173 (11)0.0476 (5)
C11−0.26884 (18)0.69666 (18)0.26178 (13)0.0581 (6)
H11−0.31560.74870.25100.070*
C12−0.28515 (18)0.60527 (19)0.22792 (13)0.0598 (6)
H12−0.34260.59660.19460.072*
C13−0.21746 (16)0.52658 (15)0.24283 (11)0.0484 (5)
H13−0.22780.46570.21880.058*
C14−0.1632 (2)0.81144 (17)0.34798 (15)0.0693 (7)
H14A−0.11930.85090.31450.083*
H14B−0.12670.80230.39590.083*
H14C−0.23030.84470.35670.083*
N1−0.01969 (13)0.45407 (11)0.38535 (9)0.0409 (4)
H1N−0.0421 (17)0.4933 (14)0.4174 (11)0.049*
O10.14949 (11)0.35731 (10)0.36476 (9)0.0497 (4)
O20.08974 (11)0.40436 (10)0.49378 (8)0.0465 (4)
O3−0.04744 (13)0.38456 (10)0.26879 (8)0.0528 (4)
Cl1−0.14827 (5)0.34034 (5)0.52560 (4)0.0706 (2)
S10.06458 (4)0.37028 (3)0.41809 (3)0.03622 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0387 (9)0.0376 (9)0.0335 (9)0.0023 (8)0.0006 (7)0.0023 (7)
C20.0403 (10)0.0532 (11)0.0422 (10)−0.0003 (9)0.0050 (8)−0.0039 (9)
C30.0539 (13)0.0707 (15)0.0656 (15)−0.0153 (12)0.0158 (12)0.0052 (12)
C40.0806 (17)0.0468 (12)0.0789 (17)−0.0165 (12)0.0058 (14)0.0043 (12)
C50.0829 (17)0.0386 (11)0.0665 (15)0.0010 (11)0.0102 (13)−0.0030 (10)
C60.0581 (12)0.0400 (10)0.0464 (11)0.0047 (9)0.0100 (10)0.0002 (9)
C70.0421 (10)0.0362 (9)0.0362 (9)−0.0064 (8)−0.0011 (8)0.0008 (7)
C80.0403 (10)0.0395 (9)0.0321 (9)−0.0028 (8)−0.0009 (7)0.0073 (7)
C90.0469 (10)0.0395 (9)0.0350 (9)−0.0003 (8)0.0001 (8)0.0052 (7)
C100.0554 (12)0.0446 (10)0.0428 (10)0.0075 (9)0.0127 (9)0.0098 (9)
C110.0504 (13)0.0652 (13)0.0587 (13)0.0154 (11)0.0049 (10)0.0234 (11)
C120.0463 (12)0.0789 (16)0.0540 (13)−0.0044 (11)−0.0136 (10)0.0220 (12)
C130.0500 (11)0.0536 (11)0.0417 (10)−0.0112 (9)−0.0079 (9)0.0090 (9)
C140.0911 (18)0.0452 (12)0.0716 (16)0.0147 (12)0.0123 (14)0.0024 (11)
N10.0514 (9)0.0365 (8)0.0349 (8)0.0099 (7)−0.0053 (7)−0.0028 (6)
O10.0420 (7)0.0497 (8)0.0576 (9)−0.0001 (6)0.0114 (7)0.0031 (7)
O20.0493 (8)0.0466 (7)0.0438 (8)0.0065 (6)−0.0130 (6)−0.0061 (6)
O30.0656 (10)0.0463 (8)0.0464 (8)0.0020 (7)−0.0051 (7)−0.0112 (6)
Cl10.0563 (4)0.0847 (4)0.0708 (4)0.0028 (3)0.0242 (3)−0.0256 (3)
S10.0360 (2)0.0358 (2)0.0368 (3)0.00304 (18)−0.00100 (18)−0.00045 (18)

Geometric parameters (Å, °)

C1—C21.387 (3)C9—C101.389 (3)
C1—C61.391 (3)C9—H90.9300
C1—S11.7691 (18)C10—C111.387 (3)
C2—C31.387 (3)C10—C141.502 (3)
C2—Cl11.738 (2)C11—C121.380 (3)
C3—C41.375 (4)C11—H110.9300
C3—H30.9300C12—C131.378 (3)
C4—C51.368 (3)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.385 (3)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—H60.9300C14—H14C0.9600
C7—O31.210 (2)N1—S11.6430 (16)
C7—N11.393 (2)N1—H1N0.819 (15)
C7—C81.484 (3)O1—S11.4192 (14)
C8—C131.389 (3)O2—S11.4333 (14)
C8—C91.394 (3)
C2—C1—C6119.43 (18)C11—C10—C9118.1 (2)
C2—C1—S1123.05 (14)C11—C10—C14121.9 (2)
C6—C1—S1117.43 (14)C9—C10—C14120.0 (2)
C1—C2—C3119.99 (19)C12—C11—C10121.0 (2)
C1—C2—Cl1121.86 (16)C12—C11—H11119.5
C3—C2—Cl1118.14 (16)C10—C11—H11119.5
C4—C3—C2119.8 (2)C13—C12—C11121.0 (2)
C4—C3—H3120.1C13—C12—H12119.5
C2—C3—H3120.1C11—C12—H12119.5
C5—C4—C3120.9 (2)C12—C13—C8119.0 (2)
C5—C4—H4119.5C12—C13—H13120.5
C3—C4—H4119.5C8—C13—H13120.5
C4—C5—C6119.8 (2)C10—C14—H14A109.5
C4—C5—H5120.1C10—C14—H14B109.5
C6—C5—H5120.1H14A—C14—H14B109.5
C5—C6—C1120.1 (2)C10—C14—H14C109.5
C5—C6—H6120.0H14A—C14—H14C109.5
C1—C6—H6120.0H14B—C14—H14C109.5
O3—C7—N1120.86 (17)C7—N1—S1124.46 (13)
O3—C7—C8124.56 (17)C7—N1—H1N119.9 (15)
N1—C7—C8114.55 (16)S1—N1—H1N115.0 (15)
C13—C8—C9119.89 (18)O1—S1—O2118.76 (9)
C13—C8—C7118.31 (17)O1—S1—N1109.39 (9)
C9—C8—C7121.80 (16)O2—S1—N1103.91 (8)
C10—C9—C8121.05 (18)O1—S1—C1107.97 (8)
C10—C9—H9119.5O2—S1—C1108.90 (8)
C8—C9—H9119.5N1—S1—C1107.39 (8)
C6—C1—C2—C30.8 (3)C8—C9—C10—C14−179.49 (19)
S1—C1—C2—C3−175.56 (17)C9—C10—C11—C12−1.1 (3)
C6—C1—C2—Cl1−178.29 (16)C14—C10—C11—C12178.7 (2)
S1—C1—C2—Cl15.3 (2)C10—C11—C12—C130.1 (3)
C1—C2—C3—C4−0.2 (4)C11—C12—C13—C81.7 (3)
Cl1—C2—C3—C4178.9 (2)C9—C8—C13—C12−2.5 (3)
C2—C3—C4—C5−0.3 (4)C7—C8—C13—C12177.57 (18)
C3—C4—C5—C60.3 (4)O3—C7—N1—S14.7 (3)
C4—C5—C6—C10.4 (4)C8—C7—N1—S1−176.87 (13)
C2—C1—C6—C5−0.9 (3)C7—N1—S1—O150.47 (18)
S1—C1—C6—C5175.69 (18)C7—N1—S1—O2178.25 (15)
O3—C7—C8—C1327.9 (3)C7—N1—S1—C1−66.46 (17)
N1—C7—C8—C13−150.47 (17)C2—C1—S1—O1179.10 (16)
O3—C7—C8—C9−152.07 (19)C6—C1—S1—O12.64 (18)
N1—C7—C8—C929.6 (2)C2—C1—S1—O248.88 (18)
C13—C8—C9—C101.4 (3)C6—C1—S1—O2−127.58 (15)
C7—C8—C9—C10−178.59 (17)C2—C1—S1—N1−63.04 (18)
C8—C9—C10—C110.4 (3)C6—C1—S1—N1120.49 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.82 (2)2.16 (2)2.974 (2)176 (2)

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5261).

References

  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1281. [PMC free article] [PubMed]

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