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Acta Cryst. (2009). E65, o1219    [ doi:10.1107/S1600536809016377 ]

4-Methyl-N-phenylbenzenesulfonamide

B. T. Gowda, S. Foro, P. G. Nirmala, H. Terao and H. Fuess

Abstract top

In the title compound, C13H13NO2S, the dihedral angle between the aromatic rings is 68.4 (1)°. In the crystal, the molecules are linked into inversion dimers by pairs of N-H...O hydrogen bonds. The unit cell of this compound was reported previously [Oh et al. (1985). Chung. Kwa. Yong. (Chung. J. Sci.), 12, 67] but no atomic coordinates were established in the earlier study.

Comment top

As part of a study of the effect of substituent on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009a, b, c), in the present work, the structure of 4-methyl-N-(phenyl)- benzenesulfonamide (I) has been determined. The conformations of the N—C bond in the C—SO2—NH—C segment of the structure are "trans" and "gauche" with respect to the S══O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of -51.6 (3)°. The two benzene rings in (I) are tilted relative to each other by 68.4 (1)°. The other bond parameters in (I) are similar to those observed in 2,4-dimethyl-N-(phenyl)-benzenesulfonamide (Gowda et al., 2009 a), 4-chloro-2-methyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2009 b), 4-methyl-N-(3,4-dimethylphenyl)- benzenesulfonamide (Gowda et al., 2009 c)) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The N—H···O hydrogen bonds (Table 1) pack the molecules into column like chains in the direction of a- axis (Fig. 2).

Related literature top

For background literature, see: Gelbrich et al. (2007); Gowda et al. (2005, 2009a,b); Gowda et al. (2009); Perlovich et al. (2006).

Experimental top

The purity of the commercial sample was checked and characterized by recording its infrared and NMR spectra (Gowda et al., 2005). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement top

The N-bound H atom was located in difference map and its positional parameters were refined freely [N—H = 0.77 (4) Å]. The other H atoms were positioned with idealized geometry using a riding model [C—H = 0.93–0.96 Å] with Uiso(H) = 1.2 Ueq(N)

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
4-Methyl-N-phenylbenzenesulfonamide top
Crystal data top
C13H13NO2SF000 = 520
Mr = 247.30Dx = 1.285 Mg m−3
Monoclinic, P21/cCu Kα radiation
λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.770 (2) Åθ = 5.4–20.7º
b = 9.768 (2) ŵ = 2.17 mm−1
c = 16.234 (5) ÅT = 299 K
β = 113.200 (2)ºPrism, colourless
V = 1278.2 (6) Å30.55 × 0.50 × 0.40 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.096
Radiation source: fine-focus sealed tubeθmax = 66.9º
Monochromator: graphiteθmin = 5.4º
T = 299 Kh = −3→10
ω/2θ scansk = −11→0
Absorption correction: ψ scan
(North et al., 1968)		l = −19→19
Tmin = 0.336, Tmax = 0.4203 standard reflections
3091 measured reflections every 120 min
2278 independent reflections intensity decay: 2.0%
2041 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.071  w = 1/[σ2(Fo2) + (0.1256P)2 + 0.4489P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.217(Δ/σ)max = 0.023
S = 1.10Δρmax = 0.47 e Å−3
2278 reflectionsΔρmin = −0.50 e Å−3
159 parametersExtinction correction: (SHELXL97; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.060 (5)
Secondary atom site location: difference Fourier map
Crystal data top
C13H13NO2SV = 1278.2 (6) Å3
Mr = 247.30Z = 4
Monoclinic, P21/cCu Kα
a = 8.770 (2) ŵ = 2.17 mm−1
b = 9.768 (2) ÅT = 299 K
c = 16.234 (5) Å0.55 × 0.50 × 0.40 mm
β = 113.200 (2)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		2041 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.096
Tmin = 0.336, Tmax = 0.4203 standard reflections
3091 measured reflections every 120 min
2278 independent reflections intensity decay: 2.0%
Refinement top
R[F2 > 2σ(F2)] = 0.071159 parameters
wR(F2) = 0.217H atoms treated by a mixture of
independent and constrained refinement
S = 1.10Δρmax = 0.47 e Å−3
2278 reflectionsΔρmin = −0.50 e Å−3
Special details top

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) top
xyzUiso*/Ueq
C10.3623 (4)0.2024 (3)0.4713 (2)0.0641 (7)
C20.2930 (5)0.0780 (4)0.4369 (2)0.0810 (9)
H20.27680.05350.37870.097*
C30.2480 (5)−0.0098 (4)0.4897 (3)0.0929 (11)
H30.2037−0.09490.46700.112*
C40.2669 (4)0.0254 (4)0.5752 (3)0.0866 (11)
C50.3360 (5)0.1527 (5)0.6073 (3)0.0881 (11)
H50.34950.17900.66480.106*
C60.3838 (4)0.2390 (4)0.5571 (2)0.0799 (9)
H60.43130.32300.58040.096*
C70.1172 (4)0.4284 (3)0.3472 (2)0.0708 (8)
C80.0374 (5)0.3408 (4)0.2771 (3)0.0855 (10)
H80.09720.28920.25190.103*
C9−0.1321 (5)0.3311 (5)0.2450 (3)0.0982 (13)
H9−0.18670.27120.19810.118*
C10−0.2223 (5)0.4065 (6)0.2800 (4)0.1095 (16)
H10−0.33720.39870.25700.131*
C11−0.1428 (6)0.4932 (6)0.3488 (4)0.1133 (16)
H11−0.20420.54570.37250.136*
C120.0292 (5)0.5048 (4)0.3844 (3)0.0899 (11)
H120.08330.56310.43240.108*
C130.2197 (7)−0.0689 (6)0.6336 (4)0.1236 (18)
H13A0.1824−0.15440.60320.148*
H13B0.1322−0.02830.64680.148*
H13C0.3142−0.08450.68840.148*
N10.2939 (3)0.4457 (3)0.3838 (2)0.0762 (8)
H1N0.318 (5)0.497 (5)0.423 (3)0.091*
O10.5798 (3)0.3739 (3)0.45932 (19)0.0863 (8)
O20.4014 (3)0.2496 (3)0.32444 (16)0.0858 (8)
S10.42133 (9)0.31592 (8)0.40573 (5)0.0689 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0670 (15)0.0712 (17)0.0583 (16)0.0062 (12)0.0292 (13)−0.0007 (13)
C20.104 (2)0.077 (2)0.071 (2)−0.0127 (17)0.0435 (18)−0.0128 (16)
C30.111 (3)0.077 (2)0.103 (3)−0.0077 (19)0.055 (2)0.001 (2)
C40.091 (2)0.095 (2)0.091 (2)0.029 (2)0.054 (2)0.029 (2)
C50.103 (2)0.106 (3)0.066 (2)0.017 (2)0.0442 (18)0.0030 (19)
C60.095 (2)0.086 (2)0.0664 (19)0.0000 (17)0.0399 (17)−0.0132 (16)
C70.0718 (17)0.0718 (18)0.0711 (18)−0.0004 (13)0.0305 (14)0.0198 (14)
C80.089 (2)0.091 (2)0.076 (2)−0.0102 (18)0.0330 (18)0.0057 (18)
C90.084 (2)0.106 (3)0.090 (3)−0.013 (2)0.019 (2)0.019 (2)
C100.079 (2)0.121 (4)0.114 (4)−0.003 (2)0.023 (2)0.038 (3)
C110.094 (3)0.127 (4)0.128 (4)0.030 (3)0.054 (3)0.028 (3)
C120.090 (2)0.088 (2)0.095 (3)0.0093 (18)0.0404 (19)0.008 (2)
C130.143 (4)0.120 (4)0.140 (4)0.033 (3)0.090 (3)0.052 (3)
N10.0754 (16)0.0734 (17)0.0824 (19)−0.0075 (12)0.0341 (14)−0.0006 (13)
O10.0727 (13)0.0901 (16)0.1026 (18)−0.0101 (11)0.0414 (12)−0.0152 (14)
O20.1054 (17)0.0989 (18)0.0709 (14)−0.0013 (14)0.0541 (13)−0.0068 (12)
S10.0721 (6)0.0749 (6)0.0691 (6)−0.0036 (3)0.0379 (4)−0.0048 (3)
Geometric parameters (Å, °) top
C1—C21.374 (5)C8—H80.9300
C1—C61.378 (4)C9—C101.358 (7)
C1—S11.750 (3)C9—H90.9300
C2—C31.375 (5)C10—C111.355 (8)
C2—H20.9300C10—H100.9300
C3—C41.375 (6)C11—C121.391 (6)
C3—H30.9300C11—H110.9300
C4—C51.392 (6)C12—H120.9300
C4—C131.492 (5)C13—H13A0.9600
C5—C61.349 (5)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—H60.9300N1—S11.633 (3)
C7—C121.373 (5)N1—H1N0.77 (4)
C7—C81.375 (5)O1—S11.434 (2)
C7—N11.434 (4)O2—S11.418 (2)
C8—C91.371 (5)
C2—C1—C6120.1 (3)C8—C9—H9119.1
C2—C1—S1120.2 (2)C11—C10—C9119.2 (4)
C6—C1—S1119.7 (3)C11—C10—H10120.4
C1—C2—C3119.2 (3)C9—C10—H10120.4
C1—C2—H2120.4C10—C11—C12121.0 (5)
C3—C2—H2120.4C10—C11—H11119.5
C2—C3—C4121.5 (4)C12—C11—H11119.5
C2—C3—H3119.2C7—C12—C11118.6 (4)
C4—C3—H3119.2C7—C12—H12120.7
C3—C4—C5117.6 (3)C11—C12—H12120.7
C3—C4—C13122.3 (5)C4—C13—H13A109.5
C5—C4—C13120.1 (4)C4—C13—H13B109.5
C6—C5—C4121.7 (3)H13A—C13—H13B109.5
C6—C5—H5119.2C4—C13—H13C109.5
C4—C5—H5119.2H13A—C13—H13C109.5
C5—C6—C1119.9 (4)H13B—C13—H13C109.5
C5—C6—H6120.1C7—N1—S1122.3 (2)
C1—C6—H6120.1C7—N1—H1N109 (3)
C12—C7—C8120.7 (3)S1—N1—H1N113 (3)
C12—C7—N1117.2 (3)O2—S1—O1118.69 (15)
C8—C7—N1122.0 (3)O2—S1—N1109.20 (17)
C9—C8—C7118.7 (4)O1—S1—N1104.00 (16)
C9—C8—H8120.7O2—S1—C1108.57 (15)
C7—C8—H8120.7O1—S1—C1109.23 (16)
C10—C9—C8121.8 (5)N1—S1—C1106.47 (14)
C10—C9—H9119.1
C6—C1—C2—C3−0.9 (5)C8—C7—C12—C11−0.9 (6)
S1—C1—C2—C3179.8 (3)N1—C7—C12—C11178.3 (4)
C1—C2—C3—C41.6 (6)C10—C11—C12—C71.3 (7)
C2—C3—C4—C5−1.0 (6)C12—C7—N1—S1135.5 (3)
C2—C3—C4—C13−179.6 (4)C8—C7—N1—S1−45.3 (4)
C3—C4—C5—C6−0.3 (5)C7—N1—S1—O265.5 (3)
C13—C4—C5—C6178.3 (4)C7—N1—S1—O1−166.9 (3)
C4—C5—C6—C11.0 (6)C7—N1—S1—C1−51.6 (3)
C2—C1—C6—C5−0.3 (5)C2—C1—S1—O2−6.3 (3)
S1—C1—C6—C5178.9 (3)C6—C1—S1—O2174.5 (2)
C12—C7—C8—C9−0.1 (5)C2—C1—S1—O1−137.1 (3)
N1—C7—C8—C9−179.2 (3)C6—C1—S1—O143.7 (3)
C7—C8—C9—C100.7 (6)C2—C1—S1—N1111.2 (3)
C8—C9—C10—C11−0.4 (7)C6—C1—S1—N1−68.0 (3)
C9—C10—C11—C12−0.6 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.77 (4)2.17 (5)2.932 (4)172 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.77 (4)2.17 (5)2.932 (4)172 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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references
References top

Allen, F. H. (2002). Acta Cryst. B58, 380–388.

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632.

Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o476.

Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009b). Acta Cryst. E65, o576.

Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o877.

Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Oh, I.-K., Kim, C.-J., Suh, I.-H. & Cho, S.-I. (1985). Chung. Kwa. Yong. (Chung. J. Sci.), 12, 67. Single page reference?

Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.