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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1728.
Published online 2010 June 23. doi:  10.1107/S1600536810023287
PMCID: PMC3007076

N-Ethyl-N-(2-meth­oxy­phen­yl)benzene­sulfonamide

Abstract

In the title mol­ecule, C15H17NO3S, the C—S—N—Cbenzene torsion angle is 81.45 (16)°, and the two aromatic rings form a dihedral angle of 45.83 (12)°. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into chains parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007 [triangle]); Parari et al. (2008 [triangle]). For related structures, see: Mariam et al. (2009 [triangle]); Arshad et al. (2009 [triangle]); Asiri et al. (2009 [triangle]); Khan et al. (2010 [triangle]); Akkurt et al. (2010a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1728-scheme1.jpg

Experimental

Crystal data

  • C15H17NO3S
  • M r = 291.37
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1728-efi1.jpg
  • a = 9.3098 (5) Å
  • b = 9.5664 (6) Å
  • c = 17.1949 (10) Å
  • β = 104.040 (2)°
  • V = 1485.65 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 296 K
  • 0.15 × 0.10 × 0.06 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 13197 measured reflections
  • 3670 independent reflections
  • 1963 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.157
  • S = 0.99
  • 3670 reflections
  • 183 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.27 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/S1600536810023287/cv2735sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023287/cv2735Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

Sulfonamides are known as biologically active compounds (Ozbek et al., 2007; Parari et al., 2008). As a contribution to a structural study of sulfonamide derivatives (Mariam et al., 2009; Arshad et al., 2009; Asiri et al., 2009; Khan et al., 2010; Akkurt et al., 2010a,b) we present here the title compound, (I).

The title molecule (Fig. 1) is bent at the S atoms with the C1—S1—N1—C9 torsion angle of 81.45 (16)°. The dihedral angle between the phenyl (C1–C6) and benzene (C9–C14) rings is 45.83 (12)°.

In the crystal structure of (I), weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains parallel to b axis.

Experimental

A mixture of N-(2-methoxyphenyl)benzenesulfonamide (1.24 g, 5.0 mmol), sodium hydride (0.24 g, 10 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min and then ethyl iodide (0.4 ml, 5.0 mmol) was added. The stirring was continued further for a period of 3 h and the contents were poured over crushed ice. The precipitated product was isolated, washed and re-crystallized from methanolic solution. It was crystallized by slow evaporation of the solvent. Yield 72%.

Refinement

All H atoms bonded to C atoms were positioned geometrically and refined using a riding model, with C—H = 0.93Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(aromatic, methylene) and Uiso(H) = 1.5Ueq(methyl).

Figures

Fig. 1.
Molecular structure of (I) showing the atom labelling scheme, Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C15H17NO3SF(000) = 616
Mr = 291.37Dx = 1.303 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3431 reflections
a = 9.3098 (5) Åθ = 2.3–24.5°
b = 9.5664 (6) ŵ = 0.22 mm1
c = 17.1949 (10) ÅT = 296 K
β = 104.040 (2)°Block, colourless
V = 1485.65 (15) Å30.15 × 0.10 × 0.06 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer1963 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.045
graphiteθmax = 28.3°, θmin = 3.1°
[var phi] and ω scansh = −12→10
13197 measured reflectionsk = −11→12
3670 independent reflectionsl = −20→22

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
3670 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.27 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
S10.86267 (6)0.81474 (6)0.18075 (4)0.0619 (2)
O10.99631 (18)0.7591 (2)0.16733 (12)0.0964 (8)
O20.81194 (19)0.94809 (17)0.14864 (9)0.0771 (7)
O30.57342 (18)0.66902 (16)0.25621 (9)0.0675 (6)
N10.73281 (18)0.70249 (17)0.14324 (10)0.0532 (6)
C10.8828 (2)0.8200 (2)0.28471 (13)0.0557 (7)
C20.8216 (3)0.9285 (2)0.31844 (14)0.0687 (9)
C30.8335 (3)0.9308 (3)0.39875 (16)0.0899 (11)
C40.9055 (4)0.8251 (4)0.44612 (18)0.1036 (15)
C50.9646 (4)0.7163 (4)0.4127 (2)0.1047 (14)
C60.9558 (3)0.7136 (3)0.33214 (17)0.0809 (10)
C70.7640 (3)0.5514 (2)0.15704 (15)0.0723 (9)
C80.6825 (4)0.4652 (3)0.09012 (17)0.1080 (13)
C90.5821 (2)0.7500 (2)0.12968 (11)0.0476 (7)
C100.5011 (2)0.7321 (2)0.18716 (12)0.0498 (7)
C110.3558 (2)0.7784 (2)0.17143 (14)0.0633 (9)
C120.2933 (3)0.8395 (2)0.09883 (17)0.0740 (10)
C130.3707 (3)0.8566 (2)0.04225 (15)0.0722 (9)
C140.5157 (3)0.8111 (2)0.05732 (13)0.0605 (8)
C150.5112 (3)0.6721 (3)0.32343 (15)0.0878 (11)
H20.772101.000100.286200.0820*
H30.792601.004300.421500.1080*
H40.914400.827300.501200.1240*
H51.011100.643500.445000.1260*
H60.998600.640900.309700.0970*
H7A0.869300.535300.164500.0870*
H7B0.737100.523100.205800.0870*
H8A0.579500.463100.090500.1620*
H8B0.721400.371800.095700.1620*
H8C0.693200.504300.040400.1620*
H110.301200.768200.209700.0760*
H120.195500.869800.088300.0890*
H130.326600.89860−0.006400.0870*
H140.568800.821700.018400.0730*
H15A0.474900.764300.329500.1320*
H15B0.585500.647500.370700.1320*
H15C0.430900.606500.315700.1320*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0444 (4)0.0686 (4)0.0765 (4)−0.0128 (3)0.0219 (3)−0.0093 (3)
O10.0473 (10)0.1239 (15)0.1290 (16)−0.0121 (10)0.0426 (10)−0.0311 (12)
O20.0798 (12)0.0655 (11)0.0836 (11)−0.0281 (9)0.0152 (8)0.0088 (8)
O30.0664 (10)0.0780 (11)0.0630 (10)0.0078 (8)0.0252 (8)0.0158 (7)
N10.0449 (10)0.0534 (11)0.0631 (11)−0.0040 (8)0.0167 (8)−0.0081 (8)
C10.0362 (11)0.0496 (12)0.0761 (15)−0.0024 (9)0.0033 (10)−0.0073 (10)
C20.0755 (17)0.0528 (14)0.0751 (16)0.0057 (12)0.0132 (12)−0.0031 (11)
C30.111 (2)0.0808 (19)0.0776 (19)0.0022 (17)0.0224 (16)−0.0168 (15)
C40.127 (3)0.106 (3)0.0640 (17)−0.010 (2)−0.0037 (17)−0.0083 (16)
C50.110 (3)0.089 (2)0.087 (2)0.0113 (18)−0.0303 (18)0.0097 (17)
C60.0691 (17)0.0680 (16)0.089 (2)0.0152 (13)−0.0131 (14)−0.0081 (13)
C70.0600 (15)0.0580 (15)0.1008 (18)0.0077 (11)0.0233 (13)−0.0162 (12)
C80.143 (3)0.0672 (18)0.122 (2)−0.0313 (18)0.048 (2)−0.0282 (16)
C90.0446 (12)0.0434 (11)0.0553 (12)−0.0076 (9)0.0130 (9)−0.0070 (9)
C100.0464 (12)0.0459 (11)0.0576 (12)−0.0058 (9)0.0135 (9)−0.0012 (9)
C110.0455 (13)0.0638 (14)0.0839 (17)−0.0052 (10)0.0224 (11)−0.0003 (12)
C120.0492 (14)0.0662 (16)0.099 (2)0.0021 (11)0.0035 (13)0.0004 (13)
C130.0691 (18)0.0655 (15)0.0701 (16)−0.0038 (12)−0.0059 (13)0.0066 (12)
C140.0645 (15)0.0628 (14)0.0537 (13)−0.0128 (11)0.0132 (11)−0.0029 (10)
C150.093 (2)0.110 (2)0.0686 (17)−0.0052 (17)0.0353 (14)0.0107 (14)

Geometric parameters (Å, °)

S1—O11.4226 (19)C12—C131.354 (4)
S1—O21.4243 (17)C13—C141.382 (4)
S1—N11.6286 (18)C2—H20.9300
S1—C11.752 (2)C3—H30.9300
O3—C101.356 (2)C4—H40.9300
O3—C151.413 (3)C5—H50.9300
N1—C71.482 (3)C6—H60.9300
N1—C91.439 (3)C7—H7A0.9700
C1—C21.378 (3)C7—H7B0.9700
C1—C61.376 (3)C8—H8A0.9600
C2—C31.359 (4)C8—H8B0.9600
C3—C41.368 (5)C8—H8C0.9600
C4—C51.367 (5)C11—H110.9300
C5—C61.368 (4)C12—H120.9300
C7—C81.468 (4)C13—H130.9300
C9—C101.392 (3)C14—H140.9300
C9—C141.378 (3)C15—H15A0.9600
C10—C111.386 (3)C15—H15B0.9600
C11—C121.373 (4)C15—H15C0.9600
O1···C11i3.336 (3)C11···H15A2.6800
O1···C12i3.347 (3)C11···H15C2.9200
O2···C6ii3.300 (3)C15···H112.5800
O2···C143.113 (3)H2···O22.5300
O3···N12.734 (2)H2···C11v3.0800
O3···C23.383 (3)H2···H15Cv2.4600
O3···C72.965 (3)H3···H8Cviii2.4400
O3···C13.152 (3)H4···O1viii2.8900
O1···H11i2.7600H6···O12.6900
O1···H7A2.4400H6···O2vi2.5300
O1···H4iii2.8900H7A···O12.4400
O1···H12i2.7600H7A···C1vi3.0600
O1···H62.6900H7A···C2vi3.0000
O2···H13iv2.8800H7B···O32.3800
O2···H15Cv2.9100H7B···C102.9300
O2···H22.5300H8A···C92.8200
O2···H6ii2.5300H8A···H15Aix2.4700
O3···H7B2.3800H8C···C3iii3.0900
N1···O32.734 (2)H8C···H3iii2.4400
C1···O33.152 (3)H11···O1vii2.7600
C2···O33.383 (3)H11···C152.5800
C6···O2vi3.300 (3)H11···H15A2.2900
C6···C73.472 (4)H11···H15C2.4700
C7···C63.472 (4)H12···O1vii2.7600
C7···O32.965 (3)H13···O2iv2.8800
C11···O1vii3.336 (3)H14···H15Biii2.6000
C12···O1vii3.347 (3)H15A···C112.6800
C14···O23.113 (3)H15A···H112.2900
C1···H7Aii3.0600H15A···C8v2.9600
C2···H7Aii3.0000H15A···H8Av2.4700
C3···H8Cviii3.0900H15B···H14viii2.6000
C8···H15Aix2.9600H15C···C112.9200
C9···H8A2.8200H15C···H112.4700
C10···H7B2.9300H15C···O2ix2.9100
C11···H2ix3.0800H15C···H2ix2.4600
O1—S1—O2119.54 (11)C4—C3—H3120.00
O1—S1—N1106.47 (10)C3—C4—H4120.00
O1—S1—C1107.15 (11)C5—C4—H4120.00
O2—S1—N1107.01 (10)C4—C5—H5120.00
O2—S1—C1108.24 (10)C6—C5—H5120.00
N1—S1—C1107.96 (9)C1—C6—H6120.00
C10—O3—C15119.46 (18)C5—C6—H6120.00
S1—N1—C7118.81 (15)N1—C7—H7A109.00
S1—N1—C9117.18 (13)N1—C7—H7B109.00
C7—N1—C9118.65 (18)C8—C7—H7A109.00
S1—C1—C2119.88 (16)C8—C7—H7B109.00
S1—C1—C6119.90 (18)H7A—C7—H7B108.00
C2—C1—C6120.2 (2)C7—C8—H8A109.00
C1—C2—C3120.0 (2)C7—C8—H8B109.00
C2—C3—C4120.1 (3)C7—C8—H8C109.00
C3—C4—C5120.1 (3)H8A—C8—H8B109.00
C4—C5—C6120.6 (3)H8A—C8—H8C109.00
C1—C6—C5119.1 (3)H8B—C8—H8C109.00
N1—C7—C8112.2 (2)C10—C11—H11120.00
N1—C9—C10121.41 (17)C12—C11—H11120.00
N1—C9—C14119.11 (19)C11—C12—H12119.00
C10—C9—C14119.5 (2)C13—C12—H12119.00
O3—C10—C9115.92 (17)C12—C13—H13120.00
O3—C10—C11124.52 (19)C14—C13—H13120.00
C9—C10—C11119.56 (19)C9—C14—H14120.00
C10—C11—C12119.4 (2)C13—C14—H14120.00
C11—C12—C13121.5 (2)O3—C15—H15A109.00
C12—C13—C14119.6 (2)O3—C15—H15B109.00
C9—C14—C13120.5 (2)O3—C15—H15C109.00
C1—C2—H2120.00H15A—C15—H15B109.00
C3—C2—H2120.00H15A—C15—H15C109.00
C2—C3—H3120.00H15B—C15—H15C109.00
O1—S1—N1—C742.39 (19)S1—C1—C2—C3178.2 (2)
O1—S1—N1—C9−163.78 (15)C6—C1—C2—C30.1 (4)
O2—S1—N1—C7171.30 (16)S1—C1—C6—C5−177.1 (2)
O2—S1—N1—C9−34.87 (17)C2—C1—C6—C51.0 (4)
C1—S1—N1—C7−72.39 (18)C1—C2—C3—C4−0.4 (4)
C1—S1—N1—C981.45 (16)C2—C3—C4—C5−0.5 (5)
O1—S1—C1—C2144.01 (19)C3—C4—C5—C61.7 (6)
O1—S1—C1—C6−38.0 (2)C4—C5—C6—C1−1.9 (5)
O2—S1—C1—C213.9 (2)N1—C9—C10—O30.7 (3)
O2—S1—C1—C6−168.12 (19)N1—C9—C10—C11−179.48 (18)
N1—S1—C1—C2−101.66 (19)C14—C9—C10—O3178.90 (18)
N1—S1—C1—C676.4 (2)C14—C9—C10—C11−1.2 (3)
C15—O3—C10—C9167.2 (2)N1—C9—C14—C13179.41 (18)
C15—O3—C10—C11−12.7 (3)C10—C9—C14—C131.1 (3)
S1—N1—C7—C8−148.4 (2)O3—C10—C11—C12−179.24 (19)
C9—N1—C7—C858.1 (3)C9—C10—C11—C120.9 (3)
S1—N1—C9—C10−93.0 (2)C10—C11—C12—C13−0.5 (3)
S1—N1—C9—C1488.8 (2)C11—C12—C13—C140.4 (3)
C7—N1—C9—C1060.9 (3)C12—C13—C14—C9−0.7 (3)
C7—N1—C9—C14−117.4 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, −y+2, −z; (v) −x+1, y+1/2, −z+1/2; (vi) −x+2, y−1/2, −z+1/2; (vii) x−1, y, z; (viii) x, −y+3/2, z+1/2; (ix) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.532.905 (3)104
C6—H6···O2vi0.932.533.300 (3)140
C7—H7A···O10.972.442.911 (3)109
C7—H7B···O30.972.382.965 (3)118

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2735).

References

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