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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o326
doi:10.1107/S1600536812000177

N-Ethyl-N-(4-methyl­phen­yl)benzene­sulfonamide

Muhammad Akhyar Farrukh,a‡ Komal Faryal,a Maymoona Mahboob,a Fahim Ashraf Qureshia and Mehmet Akkurtb*

aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 29 December 2011; accepted 3 January 2012; online 11 January 2012)

The title compound, C15H17NO2S, is twisted at the S—N bond with a C—S—N—C torsion angle of 73.90 (14)°. The dihedral angle between the aromatic rings is 36.76 (11)°.

Related literature

For related structures, see: Ahmad et al. (2011[Ahmad, S., Farrukh, M. A., Qureshi, F. A., Faryal, K. & Akkurt, M. (2011). Acta Cryst. E67, o1909.]); Nirmala et al. (2011[Nirmala, P. G., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o6.]). For applications of sulfonamides, see: Faidallah et al. (2007[Faidallah, H., Al-Saadi, M., Rostom, S. & Fahmy, H. (2007). Med. Chem. Res. 16, 300-318.]); Gauss & Weinstein (1946[Gauss, H. & Weinstein, L. J. (1946). Am. J. Dig. Dis. 13, 373-375.]); Korolkovas (1988[Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed. pp. 699-716. New York: Wiley.]); Laurence (2009[Laurence, M. (2009). East Asian Sci. Tech. Soc. 3, 257-285.]).

[Scheme 1]

Experimental

Crystal data

  • C15H17NO2S

  • Mr = 275.37

  • Orthorhombic, P b c a

  • a = 15.6737 (5) Å

  • b = 8.2831 (2) Å

  • c = 22.3326 (7) Å

  • V = 2899.37 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 296 K

  • 0.20 × 0.19 × 0.15 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • 26615 measured reflections

  • 3592 independent reflections

  • 2558 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.136

  • S = 1.02

  • 3592 reflections

  • 174 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000177/is5044sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000177/is5044Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000177/is5044Isup3.cml

checkCIF report


Comment top

Sulfonamides commonly named as Sulfa drugs are the medicines capable of controlling the bacterial infections (Laurence, 2009). The phenolic azo- dyes derived from the sulfonamides have the therapeutic potentialities and special mode of action against the acute bacterial infections (Korolkovas, 1988). Some benzenesulfonamide are evaluated for their in vitro antitumor activity (Faidallah et al., 2007). Hemorrhagic colitis (i.e. swollen of Colon and diarrhea) can be the direct result of the toxic effect of the ingested sulfonamide but with the withdrawal of the sulfonamides from the body, the symptoms subsided and body returns to its normal activity (Gauss & Weinstein, 1946) As part of our ongoing studies of the effect of substitutions on the structures of N-(aryl)-arylsulfonamides (Ahmad et al., 2011), we synthesized the title compound, (I), and report herein its crystal structure.

As shown in Fig. 1, the title molecule is twisted at the S—N bond with the C10—S1—N1—C5 torsion angle of 73.90 (14)°, compared to the values of 80.2 (3)° (molecule 1) and -79.4 (3)° (molecule 2) in N-ethyl-4-methyl-N-(3-methylphenyl)benzenesulfonamide (II) (Ahmad et al., 2011), -58.4 (2) and -48.3 (2)° (molecule 1) and -75.7 (3)° (molecule 2), in the two molecules of 2,4-dimethyl-N-(4-methylphenyl)benzenesulfonamide (III) (Nirmala et al., 2011). The phenyl and benzene rings in (I) are tilted relative to each other by 36.76 (11)°, compared to the values of 35.3 (2)° (molecule 1) and 42.5 (2)° (molecule 2) in (II), and 72.0 (1)° (molecule 1) and 78.3 (1)° (molecule 2) in (III). No classical hydrogen bonds are observed in the crystal structure. The crystal packing of (I) is shown in Figs. 2 & 3 down the a and b axes, respectively.

Related literature top

For related structures, see: Ahmad et al. (2011); Nirmala et al. (2011). For applications of sulfonamides, see: Faidallah et al. (2007); Gauss & Weinstein (1946); Korolkovas (1988); Laurence (2009).

Experimental top

5 mM of p-toluidine was dissolved in 20 ml of distilled water then 5 mM of ethyl iodide was added. The reaction mixture was stirred properly and 5 mM of benzenesulfonyl chloride was added. The mixture was stirred for about 1–2 h and the pH was maintained 8–10 using 3% Na2CO3 solution. The reaction was monitored by TLC. The product obtained was filtered and the precipitate was washed with distilled water, dried and recrystallized using methanol.

Refinement top

All H atoms were geometrically positioned and refined using a riding model with C—H = 0.93–0.97 Å. The Uiso(H) values were constrained to be 1.5Ueq(methyl-C) or 1.2Ueq(other C atoms). In the final refinement one low angle reflection, 0 0 2, evidently effected by the beam stop was omitted.

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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed down the a axis in the unit cell.
[Figure 3] Fig. 3. A packing diagram of the title compound, viewed down the b axis in the unit cell.
N-Ethyl-N-(4-methylphenyl)benzenesulfonamide top
Crystal data top
C15H17NO2SF(000) = 1168
Mr = 275.37Dx = 1.262 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8605 reflections
a = 15.6737 (5) Åθ = 2.2–27.8°
b = 8.2831 (2) ŵ = 0.22 mm−1
c = 22.3326 (7) ÅT = 296 K
V = 2899.37 (15) Å3Prism, colourless
Z = 80.20 × 0.19 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer		2558 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.024
Graphite monochromatorθmax = 28.3°, θmin = 2.6°
ϕ and ω scansh = −20→20
26615 measured reflectionsk = −11→10
3592 independent reflectionsl = −29→28
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.8829P]
where P = (Fo2 + 2Fc2)/3
3592 reflections(Δ/σ)max = 0.001
174 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Crystal data top
C15H17NO2SV = 2899.37 (15) Å3
Mr = 275.37Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.6737 (5) ŵ = 0.22 mm−1
b = 8.2831 (2) ÅT = 296 K
c = 22.3326 (7) Å0.20 × 0.19 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer		2558 reflections with I > 2σ(I)
26615 measured reflectionsRint = 0.024
3592 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.02Δρmax = 0.21 e Å−3
3592 reflectionsΔρmin = −0.37 e Å−3
174 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.99560 (3)0.12782 (6)0.34475 (2)0.0552 (2)
O10.99210 (11)−0.01640 (16)0.37951 (7)0.0776 (6)
O21.07355 (8)0.1734 (2)0.31684 (8)0.0823 (6)
N10.96703 (9)0.27682 (16)0.38880 (7)0.0493 (4)
C10.69051 (18)0.1542 (4)0.55144 (12)0.1005 (11)
C20.76285 (14)0.1879 (3)0.50850 (9)0.0639 (7)
C30.84503 (14)0.1397 (2)0.52122 (9)0.0638 (7)
C40.91137 (12)0.1692 (2)0.48250 (8)0.0535 (6)
C50.89614 (10)0.24632 (18)0.42854 (8)0.0453 (5)
C60.81402 (11)0.2959 (2)0.41530 (9)0.0568 (6)
C70.74880 (12)0.2675 (3)0.45512 (9)0.0641 (7)
C80.97391 (15)0.4412 (2)0.36295 (9)0.0634 (6)
C90.97675 (16)0.5671 (2)0.41062 (11)0.0748 (8)
C100.91654 (11)0.11661 (19)0.28917 (8)0.0486 (5)
C110.92329 (12)0.2099 (2)0.23824 (8)0.0581 (6)
C120.85857 (16)0.2085 (3)0.19712 (10)0.0785 (9)
C130.78769 (16)0.1158 (4)0.20632 (12)0.0901 (10)
C140.78161 (17)0.0215 (4)0.25675 (13)0.0975 (10)
C150.84602 (15)0.0210 (3)0.29854 (10)0.0759 (8)
H1A0.644000.226200.543200.1510*
H1B0.709800.170400.591800.1510*
H1C0.671800.044600.546600.1510*
H30.855900.085800.557000.0770*
H40.966500.137500.492500.0640*
H60.802900.348600.379400.0680*
H70.694000.302800.445900.0770*
H8A0.925400.461100.337000.0760*
H8B1.025200.448100.338800.0760*
H9A0.924800.564100.433300.1120*
H9B0.983100.671600.392600.1120*
H9C1.024200.546700.436700.1120*
H110.971400.273300.231900.0700*
H120.862900.271100.162700.0940*
H130.743600.116600.178500.1080*
H140.73360−0.042500.262700.1170*
H150.84200−0.043000.332600.0910*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0479 (3)0.0516 (3)0.0661 (3)0.0083 (2)−0.0039 (2)−0.0070 (2)
O10.1042 (12)0.0495 (7)0.0790 (10)0.0247 (7)−0.0153 (8)−0.0011 (7)
O20.0418 (7)0.1055 (12)0.0996 (11)0.0043 (7)0.0069 (8)−0.0201 (10)
N10.0498 (8)0.0415 (7)0.0567 (8)−0.0032 (6)−0.0028 (7)−0.0023 (6)
C10.0921 (19)0.125 (2)0.0843 (17)−0.0261 (16)0.0305 (15)−0.0100 (16)
C20.0706 (13)0.0640 (11)0.0571 (11)−0.0154 (9)0.0070 (10)−0.0114 (9)
C30.0817 (14)0.0591 (11)0.0505 (10)−0.0076 (9)−0.0047 (10)0.0046 (8)
C40.0569 (10)0.0487 (9)0.0550 (10)−0.0009 (7)−0.0140 (8)0.0004 (8)
C50.0460 (8)0.0370 (7)0.0528 (9)−0.0030 (6)−0.0055 (7)−0.0031 (6)
C60.0520 (10)0.0608 (10)0.0575 (10)0.0024 (8)−0.0085 (8)0.0065 (8)
C70.0475 (9)0.0712 (12)0.0736 (13)0.0002 (9)−0.0037 (9)−0.0068 (10)
C80.0719 (12)0.0460 (9)0.0724 (12)−0.0116 (8)0.0050 (10)0.0038 (9)
C90.0884 (15)0.0459 (10)0.0902 (15)−0.0077 (10)0.0048 (13)−0.0074 (10)
C100.0463 (8)0.0466 (8)0.0529 (9)0.0011 (7)0.0031 (7)−0.0073 (7)
C110.0565 (10)0.0588 (10)0.0591 (11)0.0046 (8)0.0087 (9)−0.0019 (9)
C120.0863 (16)0.0874 (16)0.0619 (13)0.0235 (13)−0.0069 (12)−0.0038 (11)
C130.0702 (15)0.125 (2)0.0750 (16)0.0118 (15)−0.0198 (12)−0.0314 (16)
C140.0711 (15)0.128 (2)0.0934 (18)−0.0409 (15)−0.0007 (13)−0.0304 (18)
C150.0788 (14)0.0820 (14)0.0668 (12)−0.0338 (12)0.0015 (11)−0.0052 (11)
Geometric parameters (Å, º) top
S1—O11.4257 (15)C14—C151.375 (4)
S1—O21.4226 (15)C1—H1A0.9600
S1—N11.6406 (15)C1—H1B0.9600
S1—C101.7564 (18)C1—H1C0.9600
N1—C51.444 (2)C3—H30.9300
N1—C81.483 (2)C4—H40.9300
C1—C21.511 (4)C6—H60.9300
C2—C31.378 (3)C7—H70.9300
C2—C71.380 (3)C8—H8A0.9700
C3—C41.374 (3)C8—H8B0.9700
C4—C51.385 (2)C9—H9A0.9600
C5—C61.383 (2)C9—H9B0.9600
C6—C71.375 (3)C9—H9C0.9600
C8—C91.491 (3)C11—H110.9300
C10—C111.379 (2)C12—H120.9300
C10—C151.376 (3)C13—H130.9300
C11—C121.368 (3)C14—H140.9300
C12—C131.366 (4)C15—H150.9300
C13—C141.374 (4)
O1—S1—O2119.60 (10)H1A—C1—H1C110.00
O1—S1—N1107.06 (8)H1B—C1—H1C110.00
O1—S1—C10108.26 (9)C2—C3—H3119.00
O2—S1—N1107.31 (9)C4—C3—H3119.00
O2—S1—C10108.08 (9)C3—C4—H4120.00
N1—S1—C10105.72 (8)C5—C4—H4120.00
S1—N1—C5116.54 (11)C5—C6—H6120.00
S1—N1—C8115.94 (12)C7—C6—H6120.00
C5—N1—C8117.12 (14)C2—C7—H7119.00
C1—C2—C3121.1 (2)C6—C7—H7119.00
C1—C2—C7121.1 (2)N1—C8—H8A109.00
C3—C2—C7117.75 (19)N1—C8—H8B109.00
C2—C3—C4121.73 (18)C9—C8—H8A109.00
C3—C4—C5119.95 (17)C9—C8—H8B109.00
N1—C5—C4118.87 (15)H8A—C8—H8B108.00
N1—C5—C6122.18 (16)C8—C9—H9A109.00
C4—C5—C6118.91 (16)C8—C9—H9B110.00
C5—C6—C7120.18 (18)C8—C9—H9C109.00
C2—C7—C6121.45 (18)H9A—C9—H9B109.00
N1—C8—C9111.50 (16)H9A—C9—H9C109.00
S1—C10—C11119.94 (13)H9B—C9—H9C109.00
S1—C10—C15119.33 (15)C10—C11—H11120.00
C11—C10—C15120.64 (18)C12—C11—H11120.00
C10—C11—C12119.46 (18)C11—C12—H12120.00
C11—C12—C13120.5 (2)C13—C12—H12120.00
C12—C13—C14120.0 (2)C12—C13—H13120.00
C13—C14—C15120.5 (3)C14—C13—H13120.00
C10—C15—C14119.0 (2)C13—C14—H14120.00
C2—C1—H1A109.00C15—C14—H14120.00
C2—C1—H1B109.00C10—C15—H15120.00
C2—C1—H1C109.00C14—C15—H15121.00
H1A—C1—H1B109.00
O1—S1—N1—C5−41.37 (15)C1—C2—C3—C4179.8 (2)
O2—S1—N1—C5−170.93 (13)C7—C2—C3—C40.1 (3)
C10—S1—N1—C573.90 (14)C3—C2—C7—C61.0 (3)
O1—S1—N1—C8174.57 (14)C1—C2—C7—C6−178.8 (2)
O2—S1—N1—C845.02 (16)C2—C3—C4—C5−1.3 (3)
C10—S1—N1—C8−70.16 (15)C3—C4—C5—N1179.61 (15)
N1—S1—C10—C1187.16 (15)C3—C4—C5—C61.5 (2)
O1—S1—C10—C11−158.39 (14)C4—C5—C6—C7−0.5 (3)
O2—S1—C10—C11−27.48 (17)N1—C5—C6—C7−178.50 (17)
N1—S1—C10—C15−89.31 (17)C5—C6—C7—C2−0.8 (3)
O1—S1—C10—C1525.14 (19)S1—C10—C11—C12−175.60 (16)
O2—S1—C10—C15156.05 (17)C15—C10—C11—C120.8 (3)
C5—N1—C8—C956.2 (2)S1—C10—C15—C14175.5 (2)
S1—N1—C5—C483.55 (17)C11—C10—C15—C14−0.9 (3)
C8—N1—C5—C4−132.82 (17)C10—C11—C12—C130.1 (3)
S1—N1—C5—C6−98.45 (17)C11—C12—C13—C14−0.9 (4)
C8—N1—C5—C645.2 (2)C12—C13—C14—C150.8 (5)
S1—N1—C8—C9−159.94 (15)C13—C14—C15—C100.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O20.972.452.902 (2)108
C15—H15···O10.932.582.934 (3)103

Experimental details

Crystal data
Chemical formulaC15H17NO2S
Mr275.37
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)15.6737 (5), 8.2831 (2), 22.3326 (7)
V (Å3)2899.37 (15)
Z8
Radiation typeMo Kα
µ (mm−1)0.22
Crystal size (mm)0.20 × 0.19 × 0.15
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		26615, 3592, 2558
Rint0.024
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.136, 1.02
No. of reflections3592
No. of parameters174
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.21, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SAINT (Bruker, 2007, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

 

Footnotes

‡Additional correspondence author, e-mail: akhyar100@gmail.com.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University Lahore.

References

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o326
doi:10.1107/S1600536812000177
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