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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1772.
Published online 2010 June 26. doi:  10.1107/S1600536810023974
PMCID: PMC3006880

N-(4-Methyl­benzo­yl)benzene­sulfonamide

Abstract

In the title compound, C14H13NO3S, 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 S—N—C—O segment (r.m.s. deviation = 0.039 Å) is 77.1 (1)° and that between the sulfonyl and benzoyl benzene rings is 71.9 (1)°.

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 related structures, see: Gowda et al. (2009 [triangle]); Suchetan et al. (2009 [triangle], 2010 [triangle]).

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Object name is e-66-o1772-scheme1.jpg

Experimental

Crystal data

  • C14H13NO3S
  • M r = 275.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1772-efi1.jpg
  • a = 5.5519 (6) Å
  • b = 10.541 (1) Å
  • c = 11.105 (1) Å
  • α = 85.654 (9)°
  • β = 83.667 (9)°
  • γ = 81.949 (9)°
  • V = 638.36 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 299 K
  • 0.40 × 0.32 × 0.16 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.904, T max = 0.960
  • 4293 measured reflections
  • 2595 independent reflections
  • 2207 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.109
  • S = 1.08
  • 2595 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.30 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023974/ci5108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023974/ci5108Isup2.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., 2009, 2010), the crystal structure of N-(4-methylbenzoyl)benzenesulfonamide has been determined (Fig. 1). The conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C═O bond, similar to those observed in N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009), N-(benzoyl)-4-methylbenzenesulfonamide (III) (Suchetan et al., 2010) and N-(4-chlorobenzoyl)-benzenesulfonamide (IV) (Suchetan et al., 2009).

The molecules are twisted at the S—N bonds with the C—SO2—NH—C torsional angle of 67.4 (1)°, compared to the values of -66.9 (3)° in (II), 73.2 (2)° in (III) and 69.4 (2)° in (IV).

The dihedral angle between the sulfonyl-bound benzene ring and the S—N—C—O segment (r.m.s. deviation 0.039 Å) is 77.1 (1)°, compared to the values of 86.5 (1)° in (II), 76.5 (1)° in (III) and 75.7 (1)° in (IV).

The dihedral angle between the sulfonyl and the benzoyl benzene rings is 71.9 (1)°, compared to the values of 80.3 (1) in (II), 79.4 (1)° in (III), and 68.6 (1)° in (IV).

Experimental

The title compound was prepared by refluxing a mixture of 4-methylbenzoic acid, benzenesulfonamide 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 a sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized. Colourless needle-shaped 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

H atoms were positioned with idealized geometry using a riding model with N–H = 0.86 Å, C–H = 0.93–0.96 Å and 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.

Crystal data

C14H13NO3SZ = 2
Mr = 275.31F(000) = 288
Triclinic, P1Dx = 1.432 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.5519 (6) ÅCell parameters from 2679 reflections
b = 10.541 (1) Åθ = 2.6–27.7°
c = 11.105 (1) ŵ = 0.26 mm1
α = 85.654 (9)°T = 299 K
β = 83.667 (9)°Needle, colourless
γ = 81.949 (9)°0.40 × 0.32 × 0.16 mm
V = 638.36 (11) Å3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2595 independent reflections
Radiation source: fine-focus sealed tube2207 reflections with I > 2σ(I)
graphiteRint = 0.017
Rotation method data acquisition using ω and [var phi] scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −6→6
Tmin = 0.904, Tmax = 0.960k = −13→11
4293 measured reflectionsl = −13→12

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0564P)2 + 0.1768P] where P = (Fo2 + 2Fc2)/3
2595 reflections(Δ/σ)max = 0.020
173 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

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
C10.0535 (3)0.17087 (15)0.37945 (14)0.0370 (3)
C20.2512 (3)0.07861 (18)0.39763 (17)0.0491 (4)
H20.37090.09440.44480.059*
C30.2687 (4)−0.03734 (19)0.34486 (19)0.0557 (5)
H30.4008−0.10010.35670.067*
C40.0919 (4)−0.06031 (17)0.27507 (18)0.0514 (5)
H40.1050−0.13830.23940.062*
C5−0.1047 (4)0.03194 (19)0.25778 (17)0.0517 (5)
H5−0.22410.01570.21060.062*
C6−0.1262 (3)0.14869 (17)0.31001 (16)0.0439 (4)
H6−0.25920.21100.29850.053*
C70.1508 (3)0.45512 (14)0.24545 (14)0.0362 (3)
C80.2982 (3)0.55415 (14)0.18611 (13)0.0345 (3)
C90.4790 (3)0.60283 (16)0.23892 (15)0.0393 (4)
H90.51130.57480.31770.047*
C100.6111 (3)0.69266 (17)0.17506 (15)0.0429 (4)
H100.73280.72350.21130.051*
C110.5653 (3)0.73765 (16)0.05771 (15)0.0403 (4)
C120.3825 (3)0.69012 (18)0.00681 (16)0.0471 (4)
H120.34770.7197−0.07120.056*
C130.2508 (3)0.60001 (17)0.06897 (15)0.0451 (4)
H130.12910.56950.03240.054*
C140.7134 (4)0.83301 (19)−0.01353 (19)0.0553 (5)
H14A0.84090.7882−0.06610.066*
H14B0.78440.87950.04150.066*
H14C0.60900.8920−0.06130.066*
N10.2026 (3)0.40757 (13)0.36175 (13)0.0466 (4)
H1N0.33190.42620.38870.056*
O10.1439 (3)0.29602 (14)0.55935 (12)0.0705 (5)
O2−0.2229 (3)0.37520 (13)0.45410 (13)0.0618 (4)
O3−0.0051 (2)0.41356 (12)0.19791 (11)0.0493 (3)
S10.02709 (9)0.31703 (4)0.45017 (4)0.04709 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0466 (9)0.0344 (8)0.0314 (8)−0.0135 (7)−0.0018 (6)0.0008 (6)
C20.0481 (10)0.0518 (10)0.0501 (10)−0.0113 (8)−0.0125 (8)−0.0001 (8)
C30.0556 (11)0.0452 (10)0.0633 (12)−0.0003 (8)−0.0039 (9)0.0008 (9)
C40.0641 (12)0.0386 (9)0.0524 (11)−0.0164 (8)0.0059 (9)−0.0079 (8)
C50.0555 (11)0.0545 (11)0.0510 (11)−0.0219 (9)−0.0081 (8)−0.0105 (8)
C60.0453 (9)0.0427 (9)0.0453 (9)−0.0096 (7)−0.0076 (7)−0.0014 (7)
C70.0448 (9)0.0310 (8)0.0330 (8)−0.0035 (6)−0.0065 (6)−0.0027 (6)
C80.0391 (8)0.0319 (8)0.0313 (8)−0.0004 (6)−0.0035 (6)−0.0018 (6)
C90.0429 (9)0.0439 (9)0.0313 (8)−0.0054 (7)−0.0071 (6)0.0016 (6)
C100.0417 (9)0.0476 (9)0.0408 (9)−0.0092 (7)−0.0061 (7)−0.0030 (7)
C110.0419 (9)0.0359 (8)0.0397 (8)0.0000 (7)0.0026 (7)−0.0005 (6)
C120.0571 (11)0.0495 (10)0.0342 (8)−0.0070 (8)−0.0097 (7)0.0074 (7)
C130.0524 (10)0.0494 (10)0.0366 (9)−0.0127 (8)−0.0145 (7)0.0030 (7)
C140.0585 (12)0.0500 (11)0.0552 (11)−0.0114 (9)0.0036 (9)0.0053 (9)
N10.0680 (10)0.0420 (8)0.0359 (7)−0.0246 (7)−0.0154 (7)0.0053 (6)
O10.1269 (14)0.0621 (9)0.0333 (7)−0.0439 (9)−0.0218 (7)0.0059 (6)
O20.0745 (10)0.0493 (8)0.0565 (8)−0.0036 (7)0.0148 (7)−0.0111 (6)
O30.0544 (7)0.0519 (7)0.0459 (7)−0.0172 (6)−0.0166 (6)0.0056 (5)
S10.0756 (3)0.0393 (2)0.0295 (2)−0.0204 (2)−0.00330 (19)−0.00178 (16)

Geometric parameters (Å, °)

C1—C61.381 (2)C9—C101.384 (2)
C1—C21.382 (3)C9—H90.93
C1—S11.7626 (16)C10—C111.391 (2)
C2—C31.382 (3)C10—H100.93
C2—H20.93C11—C121.383 (2)
C3—C41.373 (3)C11—C141.510 (2)
C3—H30.93C12—C131.377 (2)
C4—C51.376 (3)C12—H120.93
C4—H40.93C13—H130.93
C5—C61.385 (3)C14—H14A0.96
C5—H50.93C14—H14B0.96
C6—H60.93C14—H14C0.96
C7—O31.209 (2)N1—S11.6529 (15)
C7—N11.395 (2)N1—H1N0.86
C7—C81.487 (2)O1—S11.4257 (14)
C8—C91.391 (2)O2—S11.4340 (15)
C8—C131.393 (2)
C6—C1—C2121.09 (16)C9—C10—C11121.20 (16)
C6—C1—S1119.75 (13)C9—C10—H10119.4
C2—C1—S1119.13 (13)C11—C10—H10119.4
C3—C2—C1119.19 (17)C12—C11—C10117.86 (15)
C3—C2—H2120.4C12—C11—C14120.74 (16)
C1—C2—H2120.4C10—C11—C14121.39 (16)
C4—C3—C2120.29 (18)C13—C12—C11121.56 (16)
C4—C3—H3119.9C13—C12—H12119.2
C2—C3—H3119.9C11—C12—H12119.2
C3—C4—C5120.12 (17)C12—C13—C8120.55 (16)
C3—C4—H4119.9C12—C13—H13119.7
C5—C4—H4119.9C8—C13—H13119.7
C4—C5—C6120.56 (17)C11—C14—H14A109.5
C4—C5—H5119.7C11—C14—H14B109.5
C6—C5—H5119.7H14A—C14—H14B109.5
C1—C6—C5118.75 (17)C11—C14—H14C109.5
C1—C6—H6120.6H14A—C14—H14C109.5
C5—C6—H6120.6H14B—C14—H14C109.5
O3—C7—N1119.51 (15)C7—N1—S1123.07 (12)
O3—C7—C8123.77 (14)C7—N1—H1N118.5
N1—C7—C8116.70 (14)S1—N1—H1N118.5
C9—C8—C13118.37 (15)O1—S1—O2119.65 (10)
C9—C8—C7124.69 (14)O1—S1—N1103.47 (8)
C13—C8—C7116.93 (14)O2—S1—N1109.71 (8)
C10—C9—C8120.45 (15)O1—S1—C1109.18 (9)
C10—C9—H9119.8O2—S1—C1108.24 (8)
C8—C9—H9119.8N1—S1—C1105.73 (8)
C6—C1—C2—C30.2 (3)C10—C11—C12—C13−0.7 (3)
S1—C1—C2—C3178.30 (14)C14—C11—C12—C13177.89 (17)
C1—C2—C3—C40.1 (3)C11—C12—C13—C80.2 (3)
C2—C3—C4—C5−0.3 (3)C9—C8—C13—C120.8 (3)
C3—C4—C5—C60.2 (3)C7—C8—C13—C12−178.80 (16)
C2—C1—C6—C5−0.4 (3)O3—C7—N1—S1−12.2 (2)
S1—C1—C6—C5−178.42 (13)C8—C7—N1—S1168.97 (11)
C4—C5—C6—C10.2 (3)C7—N1—S1—O1−177.83 (14)
O3—C7—C8—C9−179.72 (16)C7—N1—S1—O2−49.07 (16)
N1—C7—C8—C9−0.9 (2)C7—N1—S1—C167.44 (15)
O3—C7—C8—C13−0.1 (2)C6—C1—S1—O1149.92 (14)
N1—C7—C8—C13178.70 (15)C2—C1—S1—O1−28.17 (17)
C13—C8—C9—C10−1.3 (2)C6—C1—S1—O218.16 (16)
C7—C8—C9—C10178.29 (15)C2—C1—S1—O2−159.93 (14)
C8—C9—C10—C110.8 (3)C6—C1—S1—N1−99.34 (14)
C9—C10—C11—C120.2 (3)C2—C1—S1—N182.58 (15)
C9—C10—C11—C14−178.37 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5108).

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. (2009). Acta Cryst. E65, o3156. [PMC free article] [PubMed]
  • Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010). Acta Cryst. E66, o1039. [PMC free article] [PubMed]

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