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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1510.
Published online 2010 May 29. doi:  10.1107/S1600536810019756
PMCID: PMC2979357

4-Methyl-N-(4-methyl­benzo­yl)benzene­sulfonamide

Abstract

In the title compound, C15H15NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 84.9 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.0 (1)°. In the crystal, inversion dimers linked by pairs of N—H(...)O hydrogen bonds occur.

Related literature

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 [triangle]); Suchetan et al. (2010a [triangle],b [triangle],c [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1510-scheme1.jpg

Experimental

Crystal data

  • C15H15NO3S
  • M r = 289.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1510-efi1.jpg
  • a = 23.800 (3) Å
  • b = 5.8518 (7) Å
  • c = 21.027 (3) Å
  • β = 93.51 (1)°
  • V = 2923.0 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 299 K
  • 0.34 × 0.24 × 0.12 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.927, T max = 0.973
  • 6121 measured reflections
  • 2994 independent reflections
  • 2162 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.118
  • S = 1.04
  • 2994 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.25 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/S1600536810019756/bq2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019756/bq2214Isup2.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 substituents on the crystal structures of N-aromatic sulfonamides (Gowda et al., 2009; Suchetan et al., 2010a,b,c), the structure of 4-Methyl-N-(4-methylbenzoyl)-benzenesulfonamide 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-(4-methylbenzoyl)-4-chlorobenzenesulfonamide (III) (Suchetan et al., 2010c), N-(4-chlorobenzoyl)-4- methylbenzenesulfonamide (IV) (Suchetan et al., 2010a), and N-(4-chlorobenzoyl)-4-chlorobenzenesulfonamide (V) (Suchetan et al., 2010b).

The molecules are twisted at the S atoms with the torsional angle of 62.0 (2)°, compared to the values of -66.9 (3)° in (II), 69.0 (2)° in (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 84.9 (1)°, compared to the values of 86.5 (1)° in (II), 77.2 (1)° in (III), 83.6 (1)° (molecule 1) and 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 89.0 (1)°, compared to the values of 80.3 (1)° in (II), 89.5 (1)° 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 in the crystal 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 4-methylbenzoic acid, 4-methylbenzenesulfonamide 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 colorless 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 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 = 0.93–0.96Å. 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-labeling 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

C15H15NO3SF(000) = 1216
Mr = 289.34Dx = 1.315 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2019 reflections
a = 23.800 (3) Åθ = 2.5–27.8°
b = 5.8518 (7) ŵ = 0.23 mm1
c = 21.027 (3) ÅT = 299 K
β = 93.51 (1)°Rod, colourless
V = 2923.0 (7) Å30.34 × 0.24 × 0.12 mm
Z = 8

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2994 independent reflections
Radiation source: fine-focus sealed tube2162 reflections with I > 2σ(I)
graphiteRint = 0.016
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −16→29
Tmin = 0.927, Tmax = 0.973k = −7→5
6121 measured reflectionsl = −26→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0532P)2 + 1.827P] where P = (Fo2 + 2Fc2)/3
2994 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = −0.25 e Å3

Special details

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)

xyzUiso*/Ueq
C10.29392 (8)−0.0818 (3)0.85224 (9)0.0411 (5)
C20.31864 (9)−0.2944 (3)0.85702 (11)0.0531 (6)
H20.3174−0.37910.89430.064*
C30.34511 (10)−0.3795 (4)0.80590 (12)0.0585 (6)
H30.3622−0.52220.80920.070*
C40.34694 (9)−0.2578 (4)0.74944 (11)0.0541 (6)
C50.32105 (9)−0.0467 (4)0.74553 (10)0.0517 (5)
H50.32140.03620.70780.062*
C60.29473 (8)0.0436 (4)0.79654 (9)0.0450 (5)
H60.27780.18670.79350.054*
C70.36098 (9)0.1360 (3)0.97561 (10)0.0471 (5)
C80.40479 (9)0.0804 (4)1.02664 (10)0.0462 (5)
C90.40501 (10)−0.1186 (4)1.06220 (12)0.0611 (6)
H90.3757−0.22311.05600.073*
C100.44864 (10)−0.1621 (5)1.10682 (12)0.0689 (7)
H100.4482−0.29701.13020.083*
C110.49272 (9)−0.0126 (5)1.11791 (11)0.0596 (6)
C120.49263 (10)0.1834 (5)1.08157 (12)0.0646 (7)
H120.52210.28681.08770.077*
C130.44978 (10)0.2293 (4)1.03648 (11)0.0592 (6)
H130.45100.36191.01230.071*
C140.37698 (12)−0.3559 (6)0.69460 (13)0.0850 (9)
H14A0.3637−0.50830.68590.102*
H14B0.4167−0.35940.70540.102*
H14C0.3696−0.26240.65750.102*
C150.53956 (11)−0.0630 (6)1.16734 (14)0.0872 (9)
H15A0.5749−0.06411.14760.105*
H15B0.5333−0.20961.18610.105*
H15C0.54030.05251.19980.105*
N10.31089 (7)0.0168 (3)0.97639 (8)0.0500 (5)
H1N0.3035 (9)−0.074 (3)1.0061 (8)0.060*
O10.21990 (6)−0.1306 (3)0.93756 (8)0.0651 (5)
O20.24436 (7)0.2579 (3)0.90537 (8)0.0620 (4)
O30.36862 (7)0.2731 (3)0.93398 (8)0.0666 (5)
S10.26113 (2)0.02819 (10)0.91814 (2)0.04836 (18)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0392 (10)0.0389 (11)0.0450 (11)−0.0041 (8)−0.0001 (8)0.0054 (8)
C20.0582 (13)0.0417 (12)0.0592 (13)−0.0001 (10)0.0032 (11)0.0135 (10)
C30.0579 (14)0.0411 (12)0.0763 (17)0.0022 (11)0.0026 (12)−0.0039 (11)
C40.0445 (12)0.0611 (14)0.0562 (13)−0.0105 (11)0.0002 (10)−0.0154 (11)
C50.0497 (12)0.0622 (14)0.0424 (11)−0.0088 (11)−0.0032 (9)0.0050 (10)
C60.0425 (11)0.0435 (11)0.0483 (11)−0.0014 (9)−0.0034 (9)0.0080 (9)
C70.0521 (12)0.0442 (11)0.0453 (11)−0.0004 (10)0.0062 (9)0.0027 (10)
C80.0467 (11)0.0484 (12)0.0441 (11)−0.0049 (10)0.0075 (9)0.0000 (9)
C90.0481 (13)0.0610 (14)0.0729 (16)−0.0143 (11)−0.0058 (11)0.0174 (12)
C100.0548 (14)0.0765 (17)0.0741 (17)−0.0099 (13)−0.0050 (12)0.0262 (14)
C110.0418 (12)0.0820 (18)0.0550 (13)−0.0042 (12)0.0026 (10)−0.0007 (12)
C120.0518 (13)0.0727 (17)0.0690 (16)−0.0226 (12)0.0019 (12)−0.0052 (13)
C130.0609 (14)0.0560 (14)0.0608 (14)−0.0156 (12)0.0066 (12)0.0044 (11)
C140.0774 (19)0.102 (2)0.0768 (19)0.0039 (17)0.0133 (15)−0.0287 (17)
C150.0535 (15)0.127 (3)0.0792 (19)−0.0048 (17)−0.0084 (14)0.0070 (18)
N10.0467 (10)0.0637 (12)0.0400 (9)−0.0048 (9)0.0045 (8)0.0117 (8)
O10.0416 (8)0.0903 (12)0.0635 (10)−0.0085 (8)0.0047 (7)0.0256 (9)
O20.0631 (10)0.0607 (10)0.0629 (10)0.0204 (8)0.0098 (8)0.0071 (8)
O30.0687 (11)0.0632 (10)0.0674 (10)−0.0093 (8)0.0011 (8)0.0246 (9)
S10.0402 (3)0.0579 (4)0.0472 (3)0.0026 (3)0.0052 (2)0.0111 (3)

Geometric parameters (Å, °)

C1—C21.377 (3)C9—H90.9300
C1—C61.383 (3)C10—C111.375 (3)
C1—S11.754 (2)C10—H100.9300
C2—C31.372 (3)C11—C121.378 (3)
C2—H20.9300C11—C151.506 (3)
C3—C41.387 (3)C12—C131.376 (3)
C3—H30.9300C12—H120.9300
C4—C51.381 (3)C13—H130.9300
C4—C141.507 (3)C14—H14A0.9600
C5—C61.380 (3)C14—H14B0.9600
C5—H50.9300C14—H14C0.9600
C6—H60.9300C15—H15A0.9600
C7—O31.209 (2)C15—H15B0.9600
C7—N11.382 (3)C15—H15C0.9600
C7—C81.486 (3)N1—S11.6521 (18)
C8—C91.384 (3)N1—H1N0.847 (10)
C8—C131.386 (3)O1—S11.4293 (15)
C9—C101.380 (3)O2—S11.4231 (16)
C2—C1—C6120.9 (2)C10—C11—C12117.4 (2)
C2—C1—S1118.86 (16)C10—C11—C15121.2 (2)
C6—C1—S1120.28 (16)C12—C11—C15121.4 (2)
C3—C2—C1119.0 (2)C13—C12—C11121.4 (2)
C3—C2—H2120.5C13—C12—H12119.3
C1—C2—H2120.5C11—C12—H12119.3
C2—C3—C4121.6 (2)C12—C13—C8120.9 (2)
C2—C3—H3119.2C12—C13—H13119.5
C4—C3—H3119.2C8—C13—H13119.5
C5—C4—C3118.2 (2)C4—C14—H14A109.5
C5—C4—C14121.7 (2)C4—C14—H14B109.5
C3—C4—C14120.0 (2)H14A—C14—H14B109.5
C6—C5—C4121.2 (2)C4—C14—H14C109.5
C6—C5—H5119.4H14A—C14—H14C109.5
C4—C5—H5119.4H14B—C14—H14C109.5
C5—C6—C1119.0 (2)C11—C15—H15A109.5
C5—C6—H6120.5C11—C15—H15B109.5
C1—C6—H6120.5H15A—C15—H15B109.5
O3—C7—N1120.8 (2)C11—C15—H15C109.5
O3—C7—C8122.6 (2)H15A—C15—H15C109.5
N1—C7—C8116.65 (18)H15B—C15—H15C109.5
C9—C8—C13118.1 (2)C7—N1—S1123.40 (14)
C9—C8—C7123.63 (19)C7—N1—H1N122.9 (16)
C13—C8—C7118.15 (19)S1—N1—H1N113.7 (16)
C10—C9—C8120.0 (2)O2—S1—O1118.59 (10)
C10—C9—H9120.0O2—S1—N1110.99 (10)
C8—C9—H9120.0O1—S1—N1103.62 (9)
C11—C10—C9122.2 (2)O2—S1—C1109.32 (9)
C11—C10—H10118.9O1—S1—C1109.49 (10)
C9—C10—H10118.9N1—S1—C1103.73 (9)
C6—C1—C2—C31.1 (3)C9—C10—C11—C15179.4 (3)
S1—C1—C2—C3−178.98 (17)C10—C11—C12—C130.8 (4)
C1—C2—C3—C4−0.8 (3)C15—C11—C12—C13−180.0 (2)
C2—C3—C4—C5−0.3 (3)C11—C12—C13—C80.8 (4)
C2—C3—C4—C14179.3 (2)C9—C8—C13—C12−1.8 (3)
C3—C4—C5—C61.0 (3)C7—C8—C13—C12−177.8 (2)
C14—C4—C5—C6−178.6 (2)O3—C7—N1—S16.9 (3)
C4—C5—C6—C1−0.7 (3)C8—C7—N1—S1−170.96 (15)
C2—C1—C6—C5−0.4 (3)C7—N1—S1—O2−55.3 (2)
S1—C1—C6—C5179.71 (15)C7—N1—S1—O1176.38 (18)
O3—C7—C8—C9−159.1 (2)C7—N1—S1—C162.01 (19)
N1—C7—C8—C918.7 (3)C2—C1—S1—O2173.39 (16)
O3—C7—C8—C1316.7 (3)C6—C1—S1—O2−6.7 (2)
N1—C7—C8—C13−165.5 (2)C2—C1—S1—O1−55.16 (18)
C13—C8—C9—C101.3 (4)C6—C1—S1—O1124.75 (17)
C7—C8—C9—C10177.1 (2)C2—C1—S1—N154.94 (18)
C8—C9—C10—C110.3 (4)C6—C1—S1—N1−125.15 (17)
C9—C10—C11—C12−1.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (1)2.19 (1)3.013 (2)165 (2)

Symmetry codes: (i) −x+1/2, −y−1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2214).

References

  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2516. [PMC free article] [PubMed]
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, 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. (2010a). Acta Cryst. E66, o327. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1253. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010c). Acta Cryst. E66, o1501. [PMC free article] [PubMed]

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