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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3053.
Published online 2010 November 6. doi:  10.1107/S1600536810044156
PMCID: PMC3011787

N-Benzyl-N,4-dimethyl­benzene­sulfonamide

Abstract

The mol­ecule of the title compound, C15H17NO2S, has a C—S—N—C torsion angle of 71.4 (2)°, and the dihedral angle between the benzene rings is 82.83 (16)°. In the crystal, mol­ecules are linked into chains along the b axis via C—H(...)O hydrogen bonds. A C—H(...)π inter­action is also present in the crystal structure.

Related literature

For the pharmacological activities of sulfonamides, see: Maren (1976 [triangle]); Boyd (1988 [triangle]). For our previous studies on derivatives of sulfonamide, see: Khan, Ahmad, Arshad et al. (2010 [triangle]); Khan, Ahmad, Sharif et al. (2010 [triangle]).

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Object name is e-66-o3053-scheme1.jpg

Experimental

Crystal data

  • C15H17NO2S
  • M r = 275.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3053-efi1.jpg
  • a = 15.0386 (16) Å
  • b = 8.2632 (7) Å
  • c = 12.0758 (12) Å
  • β = 105.902 (4)°
  • V = 1443.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 296 K
  • 0.28 × 0.17 × 0.09 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 13504 measured reflections
  • 3569 independent reflections
  • 1580 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.155
  • S = 1.01
  • 3569 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.24 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044156/xu5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044156/xu5070Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for providing financial support.

supplementary crystallographic information

Comment

Sulfonamides have extensively been reported for their wide variety of pharmacological activities such as antibacterial (Maren, 1976) and diuretic (Boyd, 1988). The present structure is continuous to our previous reported derivative of sulfonamide (Khan, Ahmad, Arshad et al.et al., 2010; Khan, Ahmad, Sharif et al., 2010).

In the title molecule (I), (Fig. 1), the molecule has a C4—S1—N1—C9 torsion angle of 71.4 (2)°. The dihedral angle between the sulfonyl benzene ring (C1–C6) and the phenyl ring (C10–C15) is 82.83 (16)°. In the structure, molecules are linked into chains along the b axis via C—H···O hydrogen bonding (Table 1, Fig. 2). In the structure, there is a C—H···π interaction (Table 1).

Experimental

A mixture of N-benzyl-4-methylbenzenesulfonamide (0.5 g, 2.02 mmol) and sodium hydride (0.2 g, 8.333 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min followed by the addition of methyl iodide (0.25 ml, 2.02 mmol). After the consumption of reactants (as monitored by TLC), the contents were poured over crushed ice. The precipitated product was isolated, washed, dried and recrystallized from chloroform solution to yield colourless blocks of title compound.

Refinement

All H atoms were positioned geometrically with C—H = 0.93–0.97 Å and treated as riding on their parent atoms, with Uiso(H) = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The title molecule showing the atomic numbering scheme and 30% probability displacement ellipsoids.
Fig. 2.
The packing and hydrogen bonding of the title compound in the unit cell. Hydrogen bonds are shown as dashed lines. For the sake of clarity, the H atoms not involved in the motif have been omitted.

Crystal data

C15H17NO2SF(000) = 584
Mr = 275.37Dx = 1.267 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1987 reflections
a = 15.0386 (16) Åθ = 2.8–19.5°
b = 8.2632 (7) ŵ = 0.22 mm1
c = 12.0758 (12) ÅT = 296 K
β = 105.902 (4)°Block, colourless
V = 1443.2 (2) Å30.28 × 0.17 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer1580 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.042
graphiteθmax = 28.3°, θmin = 1.4°
[var phi] and ω scansh = −19→20
13504 measured reflectionsk = −9→11
3569 independent reflectionsl = −14→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0492P)2 + 0.4014P] where P = (Fo2 + 2Fc2)/3
3569 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.24 e Å3

Special details

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)

xyzUiso*/Ueq
S10.28540 (5)0.19774 (9)0.52072 (8)0.0817 (3)
O10.33542 (16)0.3390 (2)0.5047 (3)0.1286 (12)
O20.27578 (16)0.1610 (3)0.63199 (19)0.1120 (10)
N10.18117 (15)0.2182 (2)0.4348 (2)0.0696 (9)
C10.40480 (17)−0.2407 (4)0.3876 (2)0.0683 (10)
C20.41527 (19)−0.0886 (4)0.3473 (3)0.0836 (12)
C30.38139 (19)0.0469 (4)0.3880 (3)0.0799 (11)
C40.33502 (16)0.0309 (3)0.4717 (2)0.0603 (9)
C50.32447 (17)−0.1215 (3)0.5129 (2)0.0647 (10)
C60.35966 (18)−0.2545 (3)0.4714 (2)0.0685 (10)
C70.4415 (2)−0.3883 (4)0.3416 (3)0.1029 (16)
C80.1774 (2)0.2578 (4)0.3159 (3)0.1013 (14)
C90.11230 (18)0.0967 (3)0.4439 (3)0.0719 (10)
C100.01606 (19)0.1670 (3)0.4037 (2)0.0644 (10)
C11−0.0138 (2)0.2751 (4)0.4709 (3)0.0804 (12)
C12−0.1020 (3)0.3421 (4)0.4332 (4)0.0991 (16)
C13−0.1597 (2)0.2996 (5)0.3276 (5)0.1090 (18)
C14−0.1292 (3)0.1911 (5)0.2621 (4)0.1128 (17)
C15−0.0424 (2)0.1256 (4)0.2990 (3)0.0876 (12)
H20.44620−0.076800.290800.1000*
H30.389600.148600.359300.0960*
H50.29330−0.134300.569000.0780*
H60.35270−0.356200.500800.0820*
H7A0.47420−0.455200.404600.1540*
H7B0.48270−0.355600.297500.1540*
H7C0.39090−0.448300.293300.1540*
H8A0.192000.163200.278100.1520*
H8B0.221300.341700.314900.1520*
H8C0.116300.294400.276500.1520*
H9A0.124300.061400.523200.0860*
H9B0.117000.003300.397200.0860*
H110.024900.304300.542300.0970*
H12−0.121900.415800.479500.1190*
H13−0.218500.344400.301700.1310*
H14−0.167800.160600.191000.1350*
H15−0.022900.052000.252300.1050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0745 (6)0.0657 (5)0.1035 (7)−0.0062 (4)0.0218 (4)−0.0202 (4)
O10.1010 (18)0.0631 (13)0.222 (3)−0.0296 (12)0.0449 (18)−0.0325 (16)
O20.1209 (19)0.139 (2)0.0748 (15)0.0202 (15)0.0246 (13)−0.0337 (14)
N10.0700 (15)0.0538 (13)0.0903 (17)0.0006 (11)0.0308 (13)0.0105 (12)
C10.0508 (16)0.081 (2)0.0685 (18)0.0036 (13)0.0088 (14)−0.0079 (15)
C20.072 (2)0.102 (2)0.089 (2)−0.0027 (17)0.0428 (17)0.0009 (19)
C30.075 (2)0.0688 (19)0.105 (2)−0.0117 (15)0.0399 (18)0.0143 (17)
C40.0522 (15)0.0594 (16)0.0693 (17)−0.0067 (11)0.0168 (13)−0.0028 (13)
C50.0607 (16)0.0711 (18)0.0654 (17)−0.0030 (13)0.0223 (13)0.0058 (14)
C60.0670 (17)0.0595 (16)0.0749 (19)0.0011 (13)0.0127 (15)0.0067 (14)
C70.088 (2)0.109 (3)0.106 (3)0.0236 (19)0.017 (2)−0.027 (2)
C80.100 (2)0.098 (2)0.115 (3)0.0158 (18)0.045 (2)0.051 (2)
C90.0745 (19)0.0558 (15)0.089 (2)−0.0018 (13)0.0286 (16)0.0104 (14)
C100.0669 (18)0.0530 (15)0.0741 (19)−0.0062 (13)0.0209 (15)0.0130 (14)
C110.073 (2)0.081 (2)0.086 (2)−0.0004 (16)0.0199 (17)0.0049 (18)
C120.086 (3)0.086 (2)0.138 (3)0.0105 (19)0.052 (3)0.022 (2)
C130.063 (2)0.104 (3)0.153 (4)0.003 (2)0.018 (3)0.065 (3)
C140.089 (3)0.122 (3)0.110 (3)−0.017 (2)−0.002 (2)0.031 (3)
C150.086 (2)0.085 (2)0.087 (2)−0.0165 (18)0.0154 (19)0.0012 (18)

Geometric parameters (Å, °)

S1—O11.430 (2)C14—C151.370 (6)
S1—O21.423 (2)C2—H20.9300
S1—N11.634 (2)C3—H30.9300
S1—C41.746 (3)C5—H50.9300
N1—C81.459 (4)C6—H60.9300
N1—C91.468 (3)C7—H7A0.9600
C1—C21.372 (5)C7—H7B0.9600
C1—C61.369 (4)C7—H7C0.9600
C1—C71.506 (5)C8—H8A0.9600
C2—C31.376 (5)C8—H8B0.9600
C3—C41.383 (4)C8—H8C0.9600
C4—C51.379 (3)C9—H9A0.9700
C5—C61.373 (4)C9—H9B0.9700
C9—C101.511 (4)C11—H110.9300
C10—C111.363 (4)C12—H120.9300
C10—C151.371 (4)C13—H130.9300
C11—C121.394 (6)C14—H140.9300
C12—C131.377 (7)C15—H150.9300
C13—C141.356 (6)
O1···C6i3.414 (3)H2···H7Bx2.5000
O1···C7ii3.384 (4)H3···O12.6500
O2···C8iii3.061 (4)H5···O22.5900
O1···H6i2.5300H5···C13ix2.9700
O1···H8B2.4600H6···O1v2.5300
O1···H32.6500H6···H7A2.5500
O2···H52.5900H7A···H62.5500
O2···H9A2.4400H7A···H7Axi2.3400
O2···H7Civ2.8300H7B···H22.3600
O2···H8Aiii2.8300H7B···H2viii2.5000
O2···H8Biii2.5600H7C···O2xii2.8300
C3···C83.427 (5)H8A···C32.9500
C5···C93.559 (4)H8A···C42.9200
C6···O1v3.414 (3)H8A···H9B2.4400
C7···O1ii3.384 (4)H8A···O2vi2.8300
C8···C153.434 (5)H8B···O12.4600
C8···C33.427 (5)H8B···O2vi2.5600
C8···O2vi3.061 (4)H8C···C102.6500
C9···C53.559 (4)H8C···C152.8400
C15···C83.434 (5)H8C···C15xiii3.0000
C2···H13vii3.0600H8C···H15xiii2.5200
C3···H8A2.9500H9A···O22.4400
C4···H8A2.9200H9A···H112.5500
C6···H14vii3.0900H9B···H8A2.4400
C7···H2viii3.0500H9B···H152.3700
C10···H8C2.6500H11···H9A2.5500
C13···H5ix2.9700H13···C2xiii3.0600
C15···H8C2.8400H14···C6xiii3.0900
C15···H8Cvii3.0000H15···H9B2.3700
H2···H7B2.3600H15···H8Cvii2.5200
H2···C7x3.0500
O1—S1—O2119.68 (18)C4—C5—H5120.00
O1—S1—N1106.15 (14)C6—C5—H5120.00
O1—S1—C4108.00 (14)C1—C6—H6119.00
O2—S1—N1107.07 (14)C5—C6—H6119.00
O2—S1—C4108.37 (13)C1—C7—H7A110.00
N1—S1—C4106.92 (11)C1—C7—H7B110.00
S1—N1—C8114.8 (2)C1—C7—H7C109.00
S1—N1—C9117.09 (18)H7A—C7—H7B109.00
C8—N1—C9112.9 (2)H7A—C7—H7C109.00
C2—C1—C6117.8 (3)H7B—C7—H7C109.00
C2—C1—C7121.4 (3)N1—C8—H8A109.00
C6—C1—C7120.7 (3)N1—C8—H8B109.00
C1—C2—C3121.9 (3)N1—C8—H8C109.00
C2—C3—C4119.6 (3)H8A—C8—H8B110.00
S1—C4—C3121.4 (2)H8A—C8—H8C109.00
S1—C4—C5119.77 (19)H8B—C8—H8C110.00
C3—C4—C5118.8 (2)N1—C9—H9A110.00
C4—C5—C6120.4 (2)N1—C9—H9B110.00
C1—C6—C5121.5 (2)C10—C9—H9A110.00
N1—C9—C10110.3 (2)C10—C9—H9B110.00
C9—C10—C11120.2 (3)H9A—C9—H9B108.00
C9—C10—C15121.1 (3)C10—C11—H11120.00
C11—C10—C15118.7 (3)C12—C11—H11120.00
C10—C11—C12120.3 (3)C11—C12—H12120.00
C11—C12—C13120.2 (4)C13—C12—H12120.00
C12—C13—C14118.7 (4)C12—C13—H13121.00
C13—C14—C15121.1 (4)C14—C13—H13121.00
C10—C15—C14121.0 (3)C13—C14—H14120.00
C1—C2—H2119.00C15—C14—H14119.00
C3—C2—H2119.00C10—C15—H15120.00
C2—C3—H3120.00C14—C15—H15119.00
C4—C3—H3120.00
O1—S1—N1—C850.6 (2)C7—C1—C2—C3179.5 (3)
O2—S1—N1—C8179.5 (2)C1—C2—C3—C4−0.2 (5)
C4—S1—N1—C8−64.5 (2)C2—C3—C4—C50.4 (4)
O1—S1—N1—C9−173.5 (2)C2—C3—C4—S1−176.6 (2)
O2—S1—N1—C9−44.5 (2)S1—C4—C5—C6177.2 (2)
C4—S1—N1—C971.4 (2)C3—C4—C5—C60.1 (4)
O1—S1—C4—C3−26.5 (3)C4—C5—C6—C1−0.9 (4)
O2—S1—C4—C3−157.5 (2)N1—C9—C10—C11−74.0 (3)
N1—S1—C4—C387.4 (2)N1—C9—C10—C15105.2 (3)
O1—S1—C4—C5156.6 (2)C9—C10—C11—C12179.0 (3)
O2—S1—C4—C525.5 (2)C15—C10—C11—C12−0.2 (5)
N1—S1—C4—C5−89.6 (2)C9—C10—C15—C14−179.2 (3)
C8—N1—C9—C10−68.8 (3)C11—C10—C15—C140.0 (5)
S1—N1—C9—C10154.48 (19)C10—C11—C12—C130.0 (6)
C6—C1—C2—C3−0.5 (4)C11—C12—C13—C140.5 (6)
C7—C1—C6—C5−178.9 (3)C12—C13—C14—C15−0.7 (6)
C2—C1—C6—C51.1 (4)C13—C14—C15—C100.4 (6)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) x, −y−1/2, z+1/2; (v) x, y−1, z; (vi) x, −y+1/2, z−1/2; (vii) −x, y−1/2, −z+1/2; (viii) −x+1, y−1/2, −z+1/2; (ix) −x, −y, −z+1; (x) −x+1, y+1/2, −z+1/2; (xi) −x+1, −y−1, −z+1; (xii) x, −y−1/2, z−1/2; (xiii) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 phenyl ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O20.932.592.938 (3)103
C6—H6···O1v0.932.533.414 (3)158
C8—H8B···O10.962.462.886 (5)107
C8—H8B···O2vi0.962.563.061 (4)113
C9—H9A···O20.972.442.903 (4)109
C9—H9A···Cg2ix0.972.993.721 (3)133

Symmetry codes: (v) x, y−1, z; (vi) x, −y+1/2, z−1/2; (ix) −x, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5070).

References

  • Boyd, A. E. (1988). Diabetes, 37, 847–850. [PubMed]
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Khan, I. U., Ahmad, W., Arshad, M. N., Sharif, S. & Ahmed, J. (2010). Acta Cryst. E66, o2507. [PMC free article] [PubMed]
  • Khan, I. U., Ahmad, W., Sharif, S., Ali, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1218. [PMC free article] [PubMed]
  • Maren, T. H. (1976). Annu. Rev. Pharmacol. Toxicol.16, 309–327. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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