PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1219.
Published online 2009 May 7. doi:  10.1107/S1600536809016377
PMCID: PMC2969678

4-Methyl-N-phenyl­benzene­sulfonamide

Abstract

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 [triangle]). 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 [triangle]); Gowda et al. (2005 [triangle], 2009 [triangle] a [triangle],b [triangle]); Gowda, Foro, Nirmala, Terao & Fuess (2009 [triangle]); Perlovich et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1219-scheme1.jpg

Experimental

Crystal data

  • C13H13NO2S
  • M r = 247.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1219-efi1.jpg
  • a = 8.770 (2) Å
  • b = 9.768 (2) Å
  • c = 16.234 (5) Å
  • β = 113.200 (2)°
  • V = 1278.2 (6) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 2.17 mm−1
  • T = 299 K
  • 0.55 × 0.50 × 0.40 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.336, T max = 0.420
  • 3091 measured reflections
  • 2278 independent reflections
  • 2041 reflections with I > 2σ(I)
  • R int = 0.096
  • 3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.071
  • wR(F 2) = 0.217
  • S = 1.10
  • 2278 reflections
  • 159 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.50 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/S1600536809016377/bq2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016377/bq2138Isup2.hkl

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

supplementary crystallographic information

Comment

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).

Experimental

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

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)

Figures

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

Crystal data

C13H13NO2SF(000) = 520
Mr = 247.30Dx = 1.285 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.770 (2) Åθ = 5.4–20.7°
b = 9.768 (2) ŵ = 2.17 mm1
c = 16.234 (5) ÅT = 299 K
β = 113.200 (2)°Prism, colourless
V = 1278.2 (6) Å30.55 × 0.50 × 0.40 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.096
graphiteθmax = 66.9°, θmin = 5.4°
ω/2θ scansh = −3→10
Absorption correction: ψ scan (North et al., 1968)k = −11→0
Tmin = 0.336, Tmax = 0.420l = −19→19
3091 measured reflections3 standard reflections every 120 min
2278 independent reflections intensity decay: 2.0%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.217w = 1/[σ2(Fo2) + (0.1256P)2 + 0.4489P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.023
2278 reflectionsΔρmax = 0.47 e Å3
159 parametersΔρmin = −0.50 e Å3
0 restraintsExtinction 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)

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
C10.3623 (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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2138).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • 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. [PubMed]
  • Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o476. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009b). Acta Cryst. E65, o576. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Nirmala, P. G., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o877. [PMC free article] [PubMed]
  • 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.
  • 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. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Stoe & Cie (1987). REDU4 Stoe & Cie GmbH, Darmstadt, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography