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Acta Cryst. (2010). E66, o979    [ doi:10.1107/S1600536810011219 ]

N-Ethyl-N-phenyl-p-toluenesulfonamide

I. U. Khan, Z. Haider, M. N. Arshad and S. Ali

Abstract top

In the title compound, C15H17NO2S, the aromatic rings are oriented at a dihedral angle of 32.8 (1)°. The ethyl group and phenyl ring on the N atom adopt a staggered conformation with respect to the O atoms.

Comment top

In recent literature the crystal structure of simple sulfonamide derivatives have been reported (Gowda et al., 2009) II and (Nirmala et al., 2009a,b) III & IV, which vary to the title compound (I) N-Ethyl-4-methyl-N-phenylbenzenesulfonamide in respect of ethylation at the nitrogen atom of I and substitution of methyl group at phenyl rings of III & IV. The dihedral angles between the both of the phenyl rings of all these four structures are not same as 32.79(0.10)° for I, 68.4 (1)° for II, 49.7 (1)° for III and 56.7 (3)° for IV, which may be due to substitution of alkyl groups at different position in all these molecules. The geometry around the sulphur atom S1 is distorted tertrahedral with the most distortion of 120.13(0.12)° for O1–S1–O2. No suitable hydrogen bonding have been found in the crystal structure of the molecule.

Related literature top

For related structures, see: Gowda et al. (2009); Nirmala et al. (2009a,b).

Experimental top

A mixture of 4-methyl-N-phenylbenzenesulfonamide (500 mg, 2.02 mmol), and sodium hydride (194 mg, 8.08 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of ethyl iodide (630 mg 4.04 mmol). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product filtered, washed and recrystallized with methanol under slow evaporation for diffraction studies.

Refinement top

All the C—H H-atoms were positioned gemetrically and refined using a riding model with dC–H = 0.93 Å and Uiso(H) = 1.2 Ueq for aromatic (C), with dC–H = 0.96 Å and Uiso(H) = 1.5 Ueq for methyl (C), and with dC–H = 0.97 Å and Uiso(H) = 1.2 Ueq for methylene (C). The two reflections 2 0 0 and 0 0 2 were omitted in final refinement

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The labelled diagram of (I) with 50% probability level of drawn displacement ellipsoids.
[Figure 2] Fig. 2. Unit cell packing for (I) Hydrogen atoms have been omitted for clarity.
N-Ethyl-N-phenyl-p-toluenesulfonamide top
Crystal data top
C15H17NO2SF(000) = 1168
Mr = 275.36Dx = 1.258 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2488 reflections
a = 14.1248 (6) Åθ = 2.6–23.4°
b = 10.4126 (5) ŵ = 0.22 mm−1
c = 19.7639 (10) ÅT = 296 K
V = 2906.8 (2) Å3Needle, colorless
Z = 80.32 × 0.19 × 0.16 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3599 independent reflections
Radiation source: fine-focus sealed tube1759 reflections with I > 2σ(I)
graphiteRint = 0.045
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −18→10
Tmin = 0.951, Tmax = 0.966k = −13→13
15016 measured reflectionsl = −26→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0707P)2 + 0.2464P]
where P = (Fo2 + 2Fc2)/3
3597 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C15H17NO2SV = 2906.8 (2) Å3
Mr = 275.36Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.1248 (6) ŵ = 0.22 mm−1
b = 10.4126 (5) ÅT = 296 K
c = 19.7639 (10) Å0.32 × 0.19 × 0.16 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3599 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		1759 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.966Rint = 0.045
15016 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.157Δρmax = 0.19 e Å−3
S = 1.00Δρmin = −0.31 e Å−3
3597 reflectionsAbsolute structure: ?
173 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S10.12290 (5)0.31259 (6)0.45059 (3)0.0736 (3)
O10.03439 (13)0.34190 (19)0.48260 (10)0.0982 (6)
O20.14610 (15)0.18289 (15)0.43417 (9)0.0940 (6)
N10.12528 (13)0.39272 (17)0.37947 (10)0.0670 (5)
C10.21256 (17)0.3761 (2)0.50190 (10)0.0605 (6)
C20.19340 (18)0.4774 (2)0.54450 (11)0.0678 (6)
H20.13200.50890.54810.081*
C30.2651 (2)0.5321 (2)0.58177 (12)0.0759 (7)
H30.25140.60040.61050.091*
C40.35649 (19)0.4880 (3)0.57751 (12)0.0739 (7)
C50.3742 (2)0.3868 (3)0.53525 (15)0.0852 (8)
H50.43570.35540.53190.102*
C60.3044 (2)0.3305 (2)0.49782 (13)0.0773 (7)
H60.31860.26170.46960.093*
C70.09842 (18)0.5301 (2)0.38163 (13)0.0760 (7)
H7A0.15440.58250.37490.091*
H7B0.07270.55020.42590.091*
C80.0268 (2)0.5621 (3)0.32876 (15)0.0934 (9)
H8A−0.02870.51060.33540.140*
H8B0.05280.54500.28480.140*
H8C0.01030.65130.33200.140*
C90.19267 (18)0.3535 (2)0.32926 (11)0.0625 (6)
C100.2805 (2)0.4097 (2)0.32511 (13)0.0773 (7)
H100.29750.47410.35540.093*
C110.3428 (2)0.3706 (3)0.27619 (15)0.0926 (9)
H110.40220.40860.27350.111*
C120.3186 (3)0.2762 (3)0.23123 (15)0.0975 (10)
H120.36140.25020.19820.117*
C130.2316 (3)0.2209 (3)0.23514 (14)0.0941 (9)
H130.21480.15690.20460.113*
C140.1683 (2)0.2588 (2)0.28389 (13)0.0782 (7)
H140.10900.22040.28630.094*
C150.4350 (2)0.5510 (3)0.61724 (16)0.1138 (11)
H15A0.49070.49820.61540.171*
H15B0.41560.56130.66350.171*
H15C0.44870.63370.59810.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0876 (5)0.0553 (4)0.0779 (4)−0.0172 (3)0.0110 (4)−0.0053 (3)
O10.0785 (13)0.1021 (15)0.1139 (15)−0.0314 (10)0.0304 (11)−0.0179 (11)
O20.1434 (18)0.0504 (10)0.0881 (12)−0.0189 (9)0.0111 (11)−0.0017 (8)
N10.0766 (13)0.0560 (11)0.0683 (12)−0.0052 (9)−0.0052 (10)−0.0110 (9)
C10.0756 (17)0.0524 (14)0.0535 (12)0.0029 (11)0.0093 (11)0.0042 (10)
C20.0684 (16)0.0730 (16)0.0621 (14)0.0101 (12)0.0143 (13)−0.0062 (12)
C30.087 (2)0.0846 (18)0.0561 (13)0.0084 (14)0.0035 (13)−0.0139 (12)
C40.0785 (19)0.0872 (18)0.0561 (13)0.0058 (14)−0.0046 (13)0.0069 (13)
C50.080 (2)0.094 (2)0.0811 (18)0.0276 (16)−0.0046 (15)0.0030 (15)
C60.097 (2)0.0627 (16)0.0723 (16)0.0241 (14)0.0094 (15)−0.0060 (12)
C70.0835 (18)0.0557 (15)0.0887 (17)0.0020 (11)−0.0085 (15)−0.0107 (12)
C80.100 (2)0.093 (2)0.0877 (19)0.0131 (16)−0.0141 (17)0.0042 (15)
C90.0775 (17)0.0494 (12)0.0605 (13)−0.0044 (11)−0.0115 (12)−0.0005 (10)
C100.094 (2)0.0703 (16)0.0677 (15)−0.0120 (14)−0.0053 (15)0.0000 (12)
C110.090 (2)0.107 (2)0.0802 (19)−0.0051 (17)0.0048 (17)0.0132 (18)
C120.117 (3)0.107 (2)0.0684 (19)0.030 (2)0.0103 (18)0.0146 (17)
C130.132 (3)0.082 (2)0.0681 (18)0.0105 (19)−0.0103 (19)−0.0157 (14)
C140.097 (2)0.0623 (16)0.0749 (17)−0.0058 (13)−0.0119 (15)−0.0113 (13)
C150.099 (2)0.148 (3)0.094 (2)−0.008 (2)−0.0250 (19)−0.006 (2)
Geometric parameters (Å, °) top
S1—O21.4271 (18)C7—H7B0.9700
S1—O11.4339 (19)C8—H8A0.9600
S1—N11.635 (2)C8—H8B0.9600
S1—C11.752 (2)C8—H8C0.9600
N1—C91.434 (3)C9—C101.374 (3)
N1—C71.481 (3)C9—C141.377 (3)
C1—C21.377 (3)C10—C111.370 (4)
C1—C61.384 (3)C10—H100.9300
C2—C31.375 (3)C11—C121.368 (4)
C2—H20.9300C11—H110.9300
C3—C41.373 (3)C12—C131.360 (4)
C3—H30.9300C12—H120.9300
C4—C51.368 (4)C13—C141.372 (4)
C4—C151.509 (4)C13—H130.9300
C5—C61.365 (4)C14—H140.9300
C5—H50.9300C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—C81.492 (3)C15—H15C0.9600
C7—H7A0.9700
O2—S1—O1120.13 (12)H7A—C7—H7B107.9
O2—S1—N1106.42 (10)C7—C8—H8A109.5
O1—S1—N1106.78 (12)C7—C8—H8B109.5
O2—S1—C1108.83 (12)H8A—C8—H8B109.5
O1—S1—C1107.13 (11)C7—C8—H8C109.5
N1—S1—C1106.87 (10)H8A—C8—H8C109.5
C9—N1—C7117.72 (19)H8B—C8—H8C109.5
C9—N1—S1117.59 (15)C10—C9—C14119.5 (3)
C7—N1—S1117.58 (16)C10—C9—N1121.3 (2)
C2—C1—C6118.9 (2)C14—C9—N1119.3 (2)
C2—C1—S1120.07 (19)C11—C10—C9119.7 (3)
C6—C1—S1120.97 (19)C11—C10—H10120.2
C3—C2—C1120.0 (2)C9—C10—H10120.2
C3—C2—H2120.0C12—C11—C10120.8 (3)
C1—C2—H2120.0C12—C11—H11119.6
C4—C3—C2121.4 (2)C10—C11—H11119.6
C4—C3—H3119.3C13—C12—C11119.5 (3)
C2—C3—H3119.3C13—C12—H12120.2
C5—C4—C3117.9 (3)C11—C12—H12120.2
C5—C4—C15121.2 (3)C12—C13—C14120.4 (3)
C3—C4—C15120.9 (3)C12—C13—H13119.8
C6—C5—C4122.0 (3)C14—C13—H13119.8
C6—C5—H5119.0C13—C14—C9120.1 (3)
C4—C5—H5119.0C13—C14—H14120.0
C5—C6—C1119.9 (2)C9—C14—H14120.0
C5—C6—H6120.0C4—C15—H15A109.5
C1—C6—H6120.0C4—C15—H15B109.5
N1—C7—C8111.7 (2)H15A—C15—H15B109.5
N1—C7—H7A109.3C4—C15—H15C109.5
C8—C7—H7A109.3H15A—C15—H15C109.5
N1—C7—H7B109.3H15B—C15—H15C109.5
C8—C7—H7B109.3
O2—S1—N1—C9−33.36 (19)C15—C4—C5—C6−178.5 (3)
O1—S1—N1—C9−162.81 (16)C4—C5—C6—C10.2 (4)
C1—S1—N1—C982.81 (18)C2—C1—C6—C5−0.6 (4)
O2—S1—N1—C7176.76 (17)S1—C1—C6—C5175.9 (2)
O1—S1—N1—C747.31 (19)C9—N1—C7—C880.0 (3)
C1—S1—N1—C7−67.08 (19)S1—N1—C7—C8−130.2 (2)
O2—S1—C1—C2−155.91 (18)C7—N1—C9—C1056.3 (3)
O1—S1—C1—C2−24.6 (2)S1—N1—C9—C10−93.6 (2)
N1—S1—C1—C289.5 (2)C7—N1—C9—C14−122.9 (2)
O2—S1—C1—C627.6 (2)S1—N1—C9—C1487.2 (2)
O1—S1—C1—C6158.92 (19)C14—C9—C10—C11−0.3 (4)
N1—S1—C1—C6−86.9 (2)N1—C9—C10—C11−179.5 (2)
C6—C1—C2—C30.4 (3)C9—C10—C11—C120.2 (4)
S1—C1—C2—C3−176.14 (18)C10—C11—C12—C130.1 (5)
C1—C2—C3—C40.1 (4)C11—C12—C13—C14−0.2 (5)
C2—C3—C4—C5−0.5 (4)C12—C13—C14—C90.1 (4)
C2—C3—C4—C15178.4 (2)C10—C9—C14—C130.2 (4)
C3—C4—C5—C60.3 (4)N1—C9—C14—C13179.4 (2)
Acknowledgements top

The authors acknowledge the Higher Education Commission (HEC) of Pakistan for providing a grant under the project strengthening the Materials Chemistry Laboratory at GC University Lahore. MNA also acknowledges the HEC for providing a fellowship under the International Research Support Initiative Program (IRSIP)

references
References top

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