organic compounds
4-Methyl-N-phenylbenzenesulfonamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
*Correspondence e-mail: gowdabt@yahoo.com
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 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.
Related literature
For related structures, see: Gelbrich et al. (2007); Gowda et al. (2005, 2009a,b); Gowda, Foro, Nirmala, Terao & Fuess (2009); Perlovich et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell CAD-4-PC; 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.
Supporting information
10.1107/S1600536809016377/bq2138sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809016377/bq2138Isup2.hkl
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.
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)
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell
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).C13H13NO2S | F(000) = 520 |
Mr = 247.30 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 8.770 (2) Å | θ = 5.4–20.7° |
b = 9.768 (2) Å | µ = 2.17 mm−1 |
c = 16.234 (5) Å | T = 299 K |
β = 113.200 (2)° | Prism, colourless |
V = 1278.2 (6) Å3 | 0.55 × 0.50 × 0.40 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2041 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.096 |
Graphite monochromator | θmax = 66.9°, θmin = 5.4° |
ω/2θ scans | h = −3→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→0 |
Tmin = 0.336, Tmax = 0.420 | l = −19→19 |
3091 measured reflections | 3 standard reflections every 120 min |
2278 independent reflections | intensity decay: 2.0% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.217 | w = 1/[σ2(Fo2) + (0.1256P)2 + 0.4489P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.023 |
2278 reflections | Δρmax = 0.47 e Å−3 |
159 parameters | Δρmin = −0.50 e Å−3 |
0 restraints | Extinction correction: (SHELXL97; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.060 (5) |
C13H13NO2S | V = 1278.2 (6) Å3 |
Mr = 247.30 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 8.770 (2) Å | µ = 2.17 mm−1 |
b = 9.768 (2) Å | T = 299 K |
c = 16.234 (5) Å | 0.55 × 0.50 × 0.40 mm |
β = 113.200 (2)° |
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 = 0.420 | 3 standard reflections every 120 min |
3091 measured reflections | intensity decay: 2.0% |
2278 independent reflections |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.217 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.47 e Å−3 |
2278 reflections | Δρmin = −0.50 e Å−3 |
159 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3623 (4) | 0.2024 (3) | 0.4713 (2) | 0.0641 (7) | |
C2 | 0.2930 (5) | 0.0780 (4) | 0.4369 (2) | 0.0810 (9) | |
H2 | 0.2768 | 0.0535 | 0.3787 | 0.097* | |
C3 | 0.2480 (5) | −0.0098 (4) | 0.4897 (3) | 0.0929 (11) | |
H3 | 0.2037 | −0.0949 | 0.4670 | 0.112* | |
C4 | 0.2669 (4) | 0.0254 (4) | 0.5752 (3) | 0.0866 (11) | |
C5 | 0.3360 (5) | 0.1527 (5) | 0.6073 (3) | 0.0881 (11) | |
H5 | 0.3495 | 0.1790 | 0.6648 | 0.106* | |
C6 | 0.3838 (4) | 0.2390 (4) | 0.5571 (2) | 0.0799 (9) | |
H6 | 0.4313 | 0.3230 | 0.5804 | 0.096* | |
C7 | 0.1172 (4) | 0.4284 (3) | 0.3472 (2) | 0.0708 (8) | |
C8 | 0.0374 (5) | 0.3408 (4) | 0.2771 (3) | 0.0855 (10) | |
H8 | 0.0972 | 0.2892 | 0.2519 | 0.103* | |
C9 | −0.1321 (5) | 0.3311 (5) | 0.2450 (3) | 0.0982 (13) | |
H9 | −0.1867 | 0.2712 | 0.1981 | 0.118* | |
C10 | −0.2223 (5) | 0.4065 (6) | 0.2800 (4) | 0.1095 (16) | |
H10 | −0.3372 | 0.3987 | 0.2570 | 0.131* | |
C11 | −0.1428 (6) | 0.4932 (6) | 0.3488 (4) | 0.1133 (16) | |
H11 | −0.2042 | 0.5457 | 0.3725 | 0.136* | |
C12 | 0.0292 (5) | 0.5048 (4) | 0.3844 (3) | 0.0899 (11) | |
H12 | 0.0833 | 0.5631 | 0.4324 | 0.108* | |
C13 | 0.2197 (7) | −0.0689 (6) | 0.6336 (4) | 0.1236 (18) | |
H13A | 0.1824 | −0.1544 | 0.6032 | 0.148* | |
H13B | 0.1322 | −0.0283 | 0.6468 | 0.148* | |
H13C | 0.3142 | −0.0845 | 0.6884 | 0.148* | |
N1 | 0.2939 (3) | 0.4457 (3) | 0.3838 (2) | 0.0762 (8) | |
H1N | 0.318 (5) | 0.497 (5) | 0.423 (3) | 0.091* | |
O1 | 0.5798 (3) | 0.3739 (3) | 0.45932 (19) | 0.0863 (8) | |
O2 | 0.4014 (3) | 0.2496 (3) | 0.32444 (16) | 0.0858 (8) | |
S1 | 0.42133 (9) | 0.31592 (8) | 0.40573 (5) | 0.0689 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0670 (15) | 0.0712 (17) | 0.0583 (16) | 0.0062 (12) | 0.0292 (13) | −0.0007 (13) |
C2 | 0.104 (2) | 0.077 (2) | 0.071 (2) | −0.0127 (17) | 0.0435 (18) | −0.0128 (16) |
C3 | 0.111 (3) | 0.077 (2) | 0.103 (3) | −0.0077 (19) | 0.055 (2) | 0.001 (2) |
C4 | 0.091 (2) | 0.095 (2) | 0.091 (2) | 0.029 (2) | 0.054 (2) | 0.029 (2) |
C5 | 0.103 (2) | 0.106 (3) | 0.066 (2) | 0.017 (2) | 0.0442 (18) | 0.0030 (19) |
C6 | 0.095 (2) | 0.086 (2) | 0.0664 (19) | 0.0000 (17) | 0.0399 (17) | −0.0132 (16) |
C7 | 0.0718 (17) | 0.0718 (18) | 0.0711 (18) | −0.0004 (13) | 0.0305 (14) | 0.0198 (14) |
C8 | 0.089 (2) | 0.091 (2) | 0.076 (2) | −0.0102 (18) | 0.0330 (18) | 0.0057 (18) |
C9 | 0.084 (2) | 0.106 (3) | 0.090 (3) | −0.013 (2) | 0.019 (2) | 0.019 (2) |
C10 | 0.079 (2) | 0.121 (4) | 0.114 (4) | −0.003 (2) | 0.023 (2) | 0.038 (3) |
C11 | 0.094 (3) | 0.127 (4) | 0.128 (4) | 0.030 (3) | 0.054 (3) | 0.028 (3) |
C12 | 0.090 (2) | 0.088 (2) | 0.095 (3) | 0.0093 (18) | 0.0404 (19) | 0.008 (2) |
C13 | 0.143 (4) | 0.120 (4) | 0.140 (4) | 0.033 (3) | 0.090 (3) | 0.052 (3) |
N1 | 0.0754 (16) | 0.0734 (17) | 0.0824 (19) | −0.0075 (12) | 0.0341 (14) | −0.0006 (13) |
O1 | 0.0727 (13) | 0.0901 (16) | 0.1026 (18) | −0.0101 (11) | 0.0414 (12) | −0.0152 (14) |
O2 | 0.1054 (17) | 0.0989 (18) | 0.0709 (14) | −0.0013 (14) | 0.0541 (13) | −0.0068 (12) |
S1 | 0.0721 (6) | 0.0749 (6) | 0.0691 (6) | −0.0036 (3) | 0.0379 (4) | −0.0048 (3) |
C1—C2 | 1.374 (5) | C8—H8 | 0.9300 |
C1—C6 | 1.378 (4) | C9—C10 | 1.358 (7) |
C1—S1 | 1.750 (3) | C9—H9 | 0.9300 |
C2—C3 | 1.375 (5) | C10—C11 | 1.355 (8) |
C2—H2 | 0.9300 | C10—H10 | 0.9300 |
C3—C4 | 1.375 (6) | C11—C12 | 1.391 (6) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.392 (6) | C12—H12 | 0.9300 |
C4—C13 | 1.492 (5) | C13—H13A | 0.9600 |
C5—C6 | 1.349 (5) | C13—H13B | 0.9600 |
C5—H5 | 0.9300 | C13—H13C | 0.9600 |
C6—H6 | 0.9300 | N1—S1 | 1.633 (3) |
C7—C12 | 1.373 (5) | N1—H1N | 0.77 (4) |
C7—C8 | 1.375 (5) | O1—S1 | 1.434 (2) |
C7—N1 | 1.434 (4) | O2—S1 | 1.418 (2) |
C8—C9 | 1.371 (5) | ||
C2—C1—C6 | 120.1 (3) | C8—C9—H9 | 119.1 |
C2—C1—S1 | 120.2 (2) | C11—C10—C9 | 119.2 (4) |
C6—C1—S1 | 119.7 (3) | C11—C10—H10 | 120.4 |
C1—C2—C3 | 119.2 (3) | C9—C10—H10 | 120.4 |
C1—C2—H2 | 120.4 | C10—C11—C12 | 121.0 (5) |
C3—C2—H2 | 120.4 | C10—C11—H11 | 119.5 |
C2—C3—C4 | 121.5 (4) | C12—C11—H11 | 119.5 |
C2—C3—H3 | 119.2 | C7—C12—C11 | 118.6 (4) |
C4—C3—H3 | 119.2 | C7—C12—H12 | 120.7 |
C3—C4—C5 | 117.6 (3) | C11—C12—H12 | 120.7 |
C3—C4—C13 | 122.3 (5) | C4—C13—H13A | 109.5 |
C5—C4—C13 | 120.1 (4) | C4—C13—H13B | 109.5 |
C6—C5—C4 | 121.7 (3) | H13A—C13—H13B | 109.5 |
C6—C5—H5 | 119.2 | C4—C13—H13C | 109.5 |
C4—C5—H5 | 119.2 | H13A—C13—H13C | 109.5 |
C5—C6—C1 | 119.9 (4) | H13B—C13—H13C | 109.5 |
C5—C6—H6 | 120.1 | C7—N1—S1 | 122.3 (2) |
C1—C6—H6 | 120.1 | C7—N1—H1N | 109 (3) |
C12—C7—C8 | 120.7 (3) | S1—N1—H1N | 113 (3) |
C12—C7—N1 | 117.2 (3) | O2—S1—O1 | 118.69 (15) |
C8—C7—N1 | 122.0 (3) | O2—S1—N1 | 109.20 (17) |
C9—C8—C7 | 118.7 (4) | O1—S1—N1 | 104.00 (16) |
C9—C8—H8 | 120.7 | O2—S1—C1 | 108.57 (15) |
C7—C8—H8 | 120.7 | O1—S1—C1 | 109.23 (16) |
C10—C9—C8 | 121.8 (5) | N1—S1—C1 | 106.47 (14) |
C10—C9—H9 | 119.1 | ||
C6—C1—C2—C3 | −0.9 (5) | C8—C7—C12—C11 | −0.9 (6) |
S1—C1—C2—C3 | 179.8 (3) | N1—C7—C12—C11 | 178.3 (4) |
C1—C2—C3—C4 | 1.6 (6) | C10—C11—C12—C7 | 1.3 (7) |
C2—C3—C4—C5 | −1.0 (6) | C12—C7—N1—S1 | 135.5 (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—O2 | 65.5 (3) |
C13—C4—C5—C6 | 178.3 (4) | C7—N1—S1—O1 | −166.9 (3) |
C4—C5—C6—C1 | 1.0 (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—C5 | 178.9 (3) | C6—C1—S1—O2 | 174.5 (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—O1 | 43.7 (3) |
C7—C8—C9—C10 | 0.7 (6) | C2—C1—S1—N1 | 111.2 (3) |
C8—C9—C10—C11 | −0.4 (7) | C6—C1—S1—N1 | −68.0 (3) |
C9—C10—C11—C12 | −0.6 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.77 (4) | 2.17 (5) | 2.932 (4) | 172 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H13NO2S |
Mr | 247.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 8.770 (2), 9.768 (2), 16.234 (5) |
β (°) | 113.200 (2) |
V (Å3) | 1278.2 (6) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.17 |
Crystal size (mm) | 0.55 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.336, 0.420 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3091, 2278, 2041 |
Rint | 0.096 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.217, 1.10 |
No. of reflections | 2278 |
No. of parameters | 159 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.47, −0.50 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.77 (4) | 2.17 (5) | 2.932 (4) | 172 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o476. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009b). Acta Cryst. E65, o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o877. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106–112. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Oh, I.-K., Kim, C.-J., Suh, I.-H. & Cho, S.-I. (1985). Chung. Kwa. Yong. (Chung. J. Sci.), 12, 67. Google Scholar
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
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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).