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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2516.
Published online 2009 September 26. doi:  10.1107/S1600536809037222
PMCID: PMC2970249

N-Benzo­ylbenzene­sulfonamide

Abstract

In the crystal structure of the title compound, C13H11NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O)—C segment is anti to the C=O bond. The molecule is twisted at theN atom with a dihedral angle of 86.5(1)° between the sulfonyl benzene ring and the —SO2—NH—C=O segment. Furthermore, the dihedral angle between the two benzene rings is 80.3(1)°. The crystal structure features inversion-related dimers linked by pairs of N—H(...)O(S) hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2008a [triangle],b [triangle]; 2009 [triangle]).

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Object name is e-65-o2516-scheme1.jpg

Experimental

Crystal data

  • C13H11NO3S
  • M r = 261.29
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2516-efi1.jpg
  • a = 5.8396 (7) Å
  • b = 10.178 (1) Å
  • c = 10.405 (1) Å
  • α = 90.187 (8)°
  • β = 99.074 (9)°
  • γ = 99.617 (9)°
  • V = 601.83 (11) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 2.40 mm−1
  • T = 299 K
  • 0.50 × 0.33 × 0.05 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan North et al., 1968 [triangle] T min = 0.380, T max = 0.889
  • 2354 measured reflections
  • 2125 independent reflections
  • 1962 reflections with I > 2σ(I)
  • R int = 0.011
  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.171
  • S = 1.18
  • 2125 reflections
  • 167 parameters
  • 7 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.65 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 [triangle]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 [triangle]); 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/S1600536809037222/tk2540sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037222/tk2540Isup2.hkl

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

Acknowledgments

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for an extension of his research fellowship.

supplementary crystallographic information

Comment

Diaryl acylsulfonamides are known as potent anti-tumor agents against a broad spectrum of human tumor xenografts (colon, lung, breast, ovary, and prostate) in nude mice. As part of a study of the effect of ring and the side chain substituents on the solid-state structures of N-aromatic sulfonamides (Gowda et al., 2008a,b; 2009), in the present work the structure of N-(benzoyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in the structure is anti to the C═O bond in the side-chain, similar to that observed in the acid anilides. The conformation of the N—C bond in the C—SO2—NH—C(O) segment of the structure has "gauche" torsions with respect to the SO bonds (Fig. 1). The molecule is twisted at the C(O) atom with the C—SO2—NH—C(O) torsion angle being -66.9 (3)°. The packing of molecules via N—H···O(S) hydrogen bonds (Table 1) into supramolecular dimers is shown in Fig. 2.

Experimental

Compound (I) was prepared by refluxing a mixture of benzoic acid, benzene sulfonamide and phosphorous oxy chloride for 5 h on a water bath. The resultant mixture was cooled and poured into ice-cold water. The solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. Compound (I) was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point. The compound was characterized by its characteristic aromatic C—H stretching (3061.1 cm-1), carbonyl C═O (1696.7 cm-1), N—H stretching (3280.1 cm-1), symmetric (1176.3 cm-1), and asymmetric SO2 (1335.1 cm-1) infrared absorption frequencies.

Long colorless plates of (I) were obtained from a slow evaporation of its toluene solution at room temperature.

Refinement

The H atom of the NH group was located in a difference map and and later restained to N—H = 0.86 (4) Å. 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).

The Uij components of C5 were restrained to approximate isotropic behavoir.

Figures

Fig. 1.
Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of (I) with hydrogen bonding shown as dashed lines.

Crystal data

C13H11NO3SZ = 2
Mr = 261.29F(000) = 272
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 5.8396 (7) ÅCell parameters from 25 reflections
b = 10.178 (1) Åθ = 4.3–22.9°
c = 10.405 (1) ŵ = 2.40 mm1
α = 90.187 (8)°T = 299 K
β = 99.074 (9)°Long plate, colorless
γ = 99.617 (9)°0.50 × 0.33 × 0.05 mm
V = 601.83 (11) Å3

Data collection

Enraf–Nonius CAD-4 diffractometer1962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.011
graphiteθmax = 66.9°, θmin = 4.3°
ω/2θ scansh = 0→6
Absorption correction: ψ scan North et al., 1968k = −12→11
Tmin = 0.380, Tmax = 0.889l = −12→12
2354 measured reflections3 standard reflections every 120 min
2125 independent reflections intensity decay: 1.0%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.171w = 1/[σ2(Fo2) + (0.0862P)2 + 0.5464P] where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.008
2125 reflectionsΔρmax = 0.65 e Å3
167 parametersΔρmin = −0.36 e Å3
7 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (3)

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
C10.3607 (5)0.8198 (3)0.8908 (3)0.0337 (6)
C20.2344 (5)0.9229 (3)0.8901 (3)0.0407 (7)
H20.10210.91430.93070.049*
C30.3058 (7)1.0380 (3)0.8289 (4)0.0539 (9)
H30.22191.10810.82830.065*
C40.5004 (7)1.0503 (4)0.7686 (4)0.0589 (10)
H40.54821.12880.72740.071*
C50.6248 (6)0.9472 (4)0.7688 (4)0.0583 (10)
H50.75530.95590.72660.070*
C60.5584 (5)0.8304 (4)0.8311 (3)0.0470 (8)
H60.64420.76110.83290.056*
C70.0114 (5)0.5480 (3)0.7670 (3)0.0400 (7)
C8−0.0390 (5)0.4316 (3)0.6753 (3)0.0368 (7)
C9−0.2525 (6)0.4135 (4)0.5908 (3)0.0500 (8)
H9−0.35770.47170.59650.060*
C10−0.3098 (6)0.3115 (4)0.4997 (4)0.0602 (10)
H10−0.45330.30090.44410.072*
C11−0.1570 (7)0.2248 (4)0.4897 (4)0.0564 (9)
H11−0.19580.15570.42730.068*
C120.0539 (7)0.2408 (4)0.5727 (4)0.0589 (10)
H120.15760.18180.56640.071*
C130.1137 (6)0.3429 (4)0.6649 (3)0.0492 (8)
H130.25710.35260.72050.059*
N10.2045 (5)0.5551 (3)0.8642 (3)0.0436 (7)
H1N0.262 (7)0.491 (3)0.882 (4)0.052*
O10.4799 (5)0.6424 (2)1.0568 (3)0.0629 (8)
O20.0786 (5)0.6940 (3)1.0349 (3)0.0597 (7)
O3−0.1033 (4)0.6374 (3)0.7564 (3)0.0562 (7)
S10.27661 (14)0.67612 (7)0.97654 (7)0.0416 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0246 (13)0.0344 (14)0.0396 (15)0.0060 (10)−0.0030 (11)−0.0037 (11)
C20.0305 (15)0.0399 (16)0.0508 (18)0.0101 (12)−0.0009 (12)−0.0029 (13)
C30.054 (2)0.0397 (17)0.064 (2)0.0116 (15)−0.0085 (17)0.0005 (15)
C40.057 (2)0.049 (2)0.058 (2)−0.0084 (16)−0.0088 (18)0.0092 (16)
C50.0344 (17)0.081 (3)0.054 (2)−0.0073 (17)0.0082 (15)−0.0003 (18)
C60.0320 (16)0.059 (2)0.0508 (18)0.0136 (14)0.0041 (13)−0.0049 (15)
C70.0280 (15)0.0441 (17)0.0469 (17)0.0057 (12)0.0030 (12)0.0036 (13)
C80.0280 (14)0.0415 (16)0.0392 (15)0.0050 (11)0.0013 (11)0.0046 (12)
C90.0314 (16)0.063 (2)0.0534 (19)0.0125 (14)−0.0044 (14)−0.0042 (16)
C100.0408 (19)0.076 (3)0.056 (2)0.0057 (17)−0.0116 (16)−0.0082 (18)
C110.061 (2)0.056 (2)0.0469 (19)0.0034 (17)−0.0017 (16)−0.0092 (16)
C120.061 (2)0.062 (2)0.055 (2)0.0257 (18)−0.0035 (17)−0.0090 (17)
C130.0401 (17)0.056 (2)0.0486 (18)0.0154 (14)−0.0082 (14)−0.0067 (15)
N10.0414 (15)0.0331 (13)0.0525 (16)0.0104 (11)−0.0086 (12)0.0001 (12)
O10.0787 (18)0.0431 (13)0.0567 (15)0.0186 (12)−0.0293 (13)−0.0018 (11)
O20.0647 (16)0.0593 (15)0.0575 (15)0.0008 (12)0.0278 (13)−0.0007 (12)
O30.0414 (13)0.0604 (15)0.0686 (16)0.0248 (11)−0.0031 (11)−0.0111 (12)
S10.0460 (5)0.0348 (5)0.0405 (5)0.0062 (3)−0.0023 (3)0.0006 (3)

Geometric parameters (Å, °)

C1—C21.379 (4)C8—C131.385 (5)
C1—C61.384 (4)C8—C91.392 (4)
C1—S11.756 (3)C9—C101.366 (5)
C2—C31.370 (5)C9—H90.9300
C2—H20.9300C10—C111.370 (6)
C3—C41.370 (6)C10—H100.9300
C3—H30.9300C11—C121.373 (5)
C4—C51.373 (6)C11—H110.9300
C4—H40.9300C12—C131.375 (5)
C5—C61.383 (5)C12—H120.9300
C5—H50.9300C13—H130.9300
C6—H60.9300N1—S11.650 (3)
C7—O31.212 (4)N1—H1N0.79 (3)
C7—N11.383 (4)O1—S11.432 (2)
C7—C81.479 (4)O2—S11.425 (3)
C2—C1—C6121.3 (3)C10—C9—C8121.0 (3)
C2—C1—S1119.0 (2)C10—C9—H9119.5
C6—C1—S1119.6 (2)C8—C9—H9119.5
C3—C2—C1119.4 (3)C9—C10—C11120.4 (3)
C3—C2—H2120.3C9—C10—H10119.8
C1—C2—H2120.3C11—C10—H10119.8
C4—C3—C2120.3 (3)C10—C11—C12119.4 (3)
C4—C3—H3119.9C10—C11—H11120.3
C2—C3—H3119.9C12—C11—H11120.3
C3—C4—C5120.2 (3)C11—C12—C13120.8 (3)
C3—C4—H4119.9C11—C12—H12119.6
C5—C4—H4119.9C13—C12—H12119.6
C4—C5—C6120.8 (3)C12—C13—C8120.2 (3)
C4—C5—H5119.6C12—C13—H13119.9
C6—C5—H5119.6C8—C13—H13119.9
C1—C6—C5118.1 (3)C7—N1—S1122.6 (2)
C1—C6—H6121.0C7—N1—H1N120 (3)
C5—C6—H6121.0S1—N1—H1N114 (3)
O3—C7—N1120.1 (3)O2—S1—O1119.09 (18)
O3—C7—C8122.6 (3)O2—S1—N1110.97 (15)
N1—C7—C8117.2 (3)O1—S1—N1103.63 (14)
C13—C8—C9118.2 (3)O2—S1—C1108.38 (15)
C13—C8—C7124.8 (3)O1—S1—C1109.23 (15)
C9—C8—C7117.0 (3)N1—S1—C1104.55 (14)
C6—C1—C2—C30.1 (5)C10—C11—C12—C13−0.3 (6)
S1—C1—C2—C3176.8 (2)C11—C12—C13—C80.0 (6)
C1—C2—C3—C40.2 (5)C9—C8—C13—C120.3 (5)
C2—C3—C4—C50.1 (5)C7—C8—C13—C12−177.3 (3)
C3—C4—C5—C6−0.9 (5)O3—C7—N1—S15.1 (4)
C2—C1—C6—C5−0.9 (5)C8—C7—N1—S1−177.7 (2)
S1—C1—C6—C5−177.5 (2)C7—N1—S1—O249.8 (3)
C4—C5—C6—C11.3 (5)C7—N1—S1—O1178.7 (3)
O3—C7—C8—C13164.9 (3)C7—N1—S1—C1−66.9 (3)
N1—C7—C8—C13−12.2 (5)C2—C1—S1—O2−0.3 (3)
O3—C7—C8—C9−12.7 (5)C6—C1—S1—O2176.3 (2)
N1—C7—C8—C9170.2 (3)C2—C1—S1—O1−131.5 (2)
C13—C8—C9—C10−0.3 (5)C6—C1—S1—O145.2 (3)
C7—C8—C9—C10177.5 (3)C2—C1—S1—N1118.1 (2)
C8—C9—C10—C11−0.1 (6)C6—C1—S1—N1−65.2 (3)
C9—C10—C11—C120.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.79 (3)2.22 (3)2.981 (4)163 (4)

Symmetry codes: (i) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2540).

References

  • Enraf–Nonius (1996). CAD-4-PC Enraf–Nonius, Delft, The Netherlands.
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008a). Acta Cryst. E64, o1692. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008b). Acta Cryst. E64, o1825. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o1219. [PMC free article] [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Stoe & Cie (1987). REDU4 Stoe & Cie GmbH, Darmstadt, Germany.

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