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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2980.
Published online 2010 October 30. doi:  10.1107/S1600536810043369
PMCID: PMC3009330

N-Benzyl-N-(2-meth­oxy­phen­yl)benzene­sulfonamide

Abstract

In the title mol­ecule, C20H19NO3S, the dihedral angle between the phenyl rings is 48.93 (18)°, and they make dihedral angles of 38.37 (17) and 86.50 (19)° with the benzene ring. A weak intra­molecular C—H(...)O inter­action might stabilize the mol­ecular conformation. In the crystal, weak π–π stacking inter­actions between the benzene rings [centroid–centroid distance = 3.774 (2) Å] may help to establish the packing.

Related literature

For background on the biological activity of sulfonamide derivatives, see: Ozbek et al. (2007 [triangle]); Parari et al. (2008 [triangle]). For the structures of some sulfonamide derivatives, see, for example: Asiri et al. (2009 [triangle]); Aziz-ur-Rehman et al. (2010 [triangle]).

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Object name is e-66-o2980-scheme1.jpg

Experimental

Crystal data

  • C20H19NO3S
  • M r = 353.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2980-efi1.jpg
  • a = 10.0368 (3) Å
  • b = 9.0176 (3) Å
  • c = 20.4228 (7) Å
  • β = 103.424 (2)°
  • V = 1797.92 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 296 K
  • 0.25 × 0.13 × 0.09 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • 16779 measured reflections
  • 4438 independent reflections
  • 2560 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.202
  • S = 1.04
  • 4438 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.20 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/S1600536810043369/hb5703sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043369/hb5703Isup2.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 are found in a number of natural as well as synthetic compounds. These molecules are considered as biologically very acitive compounds (Ozbek et al., 2007, Parari et al., 2008). As a contribution to a structural study of sulfonamide derivatives (Asiri et al., 2009, Aziz-ur-Rehman et al., 2010) here, we report the title compound (I).

In the molecule of (I), (Fig. 1), the bond lengths and bond angles are within the expected ranges. The geometry around S1 atom is distorted from a regular tetrahedron. The largest deviation is in the angle O2—S1—O1 [118.92 (12)°].

The dihedral angle between the phenyl rings (C1–C6) and (C15–C20) is 48.93 (18)° and they make dihedral angles of 38.37 (17) and 86.50 (19)°, respectively, with the benzene ring (C7–C12).

In the crystal structure, there is no classic hydrogen bonds. Weak intramolecular C—H···O interactions stabilize the molecular conformation. π–π stacking interactions [Cg2···Cg2 (1 - x, -y, 1 - z) = 3.774 (2) Å; Cg2 is a centroid of the C7–C12 benzene ring] contribute to the stabilization of the crystal structure. Fig. 2 show the packing diagram of (I) down the 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 45 min and the benzyl chloride (0.64 g, 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 to yield light violet blocks of (I). Yield 65%.

Refinement

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

Figures

Fig. 1.
View of the title molecule with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The packing of (I), viewing down the b axis in the unit cell. For clarity, all H atoms have been omitted.

Crystal data

C20H19NO3SF(000) = 744
Mr = 353.43Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3872 reflections
a = 10.0368 (3) Åθ = 2.5–21.8°
b = 9.0176 (3) ŵ = 0.20 mm1
c = 20.4228 (7) ÅT = 296 K
β = 103.424 (2)°Block, light violet
V = 1797.92 (10) Å30.25 × 0.13 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer2560 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.037
graphiteθmax = 28.4°, θmin = 3.3°
[var phi] and ω scansh = −13→13
16779 measured reflectionsk = −12→9
4438 independent reflectionsl = −27→25

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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.1008P)2 + 0.2694P] where P = (Fo2 + 2Fc2)/3
4438 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.20 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
S10.65180 (7)0.44517 (7)0.66852 (3)0.0726 (2)
O10.5815 (3)0.5433 (2)0.70356 (11)0.1098 (9)
O20.7233 (2)0.5054 (2)0.62194 (9)0.0897 (7)
O30.6440 (2)0.0515 (2)0.65783 (15)0.1138 (9)
N10.53841 (18)0.3280 (2)0.62738 (9)0.0636 (6)
C10.7345 (3)0.2992 (4)0.78758 (13)0.0981 (13)
C20.8243 (4)0.2106 (5)0.83247 (15)0.1226 (18)
C30.9455 (4)0.1657 (4)0.81816 (18)0.1143 (14)
C40.9776 (3)0.2066 (4)0.76011 (17)0.0971 (11)
C50.8896 (3)0.2937 (3)0.71487 (14)0.0798 (10)
C60.7687 (2)0.3409 (3)0.72877 (12)0.0691 (8)
C70.5817 (2)0.2371 (3)0.57779 (13)0.0704 (9)
C80.5683 (3)0.2888 (3)0.51265 (13)0.0787 (10)
C90.6088 (4)0.2160 (5)0.4631 (2)0.1162 (17)
C100.6693 (4)0.0790 (7)0.4816 (3)0.146 (3)
C110.6818 (3)0.0179 (4)0.5442 (3)0.1157 (16)
C120.6375 (3)0.1012 (3)0.5923 (2)0.0933 (12)
C130.7184 (5)−0.0828 (4)0.6767 (4)0.197 (3)
C140.4294 (3)0.2778 (4)0.65914 (14)0.0898 (12)
C150.2919 (2)0.2704 (2)0.61222 (11)0.0596 (7)
C160.2544 (3)0.3576 (3)0.55669 (14)0.0846 (10)
C170.1251 (4)0.3467 (6)0.51567 (19)0.1411 (19)
C180.0338 (4)0.2513 (8)0.5304 (2)0.163 (3)
C190.0679 (4)0.1656 (6)0.5857 (2)0.1312 (18)
C200.1961 (3)0.1745 (3)0.62612 (16)0.0913 (12)
H10.652500.330200.796900.1180*
H20.802800.181200.872400.1470*
H31.005900.106700.848800.1370*
H41.059600.175500.750900.1170*
H50.911400.321000.674700.0960*
H80.528000.381300.502400.0940*
H90.597200.254300.419900.1390*
H100.703200.026100.449900.1750*
H110.71880−0.076200.554100.1390*
H13A0.66840−0.164400.652500.2960*
H13B0.73040−0.098600.724200.2960*
H13C0.80640−0.075700.665900.2960*
H14A0.424800.344800.695700.1080*
H14B0.452900.180200.678400.1080*
H160.316600.425000.546400.1020*
H170.100800.405900.477500.1690*
H18−0.053300.244400.502300.1960*
H190.004000.100600.596300.1570*
H200.219300.114200.664000.1090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0824 (4)0.0642 (4)0.0690 (4)0.0044 (3)0.0130 (3)−0.0103 (3)
O10.1269 (17)0.0989 (15)0.0955 (13)0.0447 (12)0.0092 (12)−0.0309 (12)
O20.1001 (13)0.0788 (12)0.0880 (12)−0.0271 (10)0.0174 (11)0.0054 (10)
O30.0902 (15)0.0710 (13)0.164 (2)−0.0034 (10)−0.0035 (15)0.0263 (14)
N10.0586 (10)0.0718 (12)0.0640 (11)0.0007 (9)0.0216 (8)−0.0025 (9)
C10.097 (2)0.134 (3)0.0643 (15)0.0410 (19)0.0209 (14)−0.0038 (17)
C20.138 (3)0.166 (4)0.0667 (18)0.056 (3)0.0298 (19)0.014 (2)
C30.105 (2)0.141 (3)0.085 (2)0.048 (2)−0.0021 (18)−0.011 (2)
C40.0692 (17)0.115 (2)0.103 (2)0.0134 (16)0.0119 (16)−0.021 (2)
C50.0717 (16)0.0852 (18)0.0841 (17)−0.0051 (14)0.0212 (14)−0.0140 (15)
C60.0692 (14)0.0724 (15)0.0631 (13)0.0051 (11)0.0098 (11)−0.0146 (11)
C70.0557 (12)0.0657 (15)0.0943 (18)−0.0151 (11)0.0269 (12)−0.0128 (13)
C80.0878 (17)0.0890 (18)0.0696 (15)−0.0247 (14)0.0391 (13)−0.0114 (14)
C90.110 (3)0.142 (3)0.116 (3)−0.047 (2)0.066 (2)−0.053 (3)
C100.094 (3)0.162 (5)0.203 (5)−0.054 (3)0.078 (3)−0.108 (4)
C110.0668 (17)0.076 (2)0.206 (4)−0.0154 (15)0.035 (2)−0.056 (3)
C120.0590 (14)0.0666 (17)0.152 (3)−0.0187 (13)0.0200 (17)−0.018 (2)
C130.128 (3)0.080 (3)0.363 (9)0.005 (2)0.014 (4)0.065 (4)
C140.0643 (14)0.134 (3)0.0764 (16)0.0061 (15)0.0273 (13)0.0290 (17)
C150.0608 (12)0.0625 (13)0.0620 (12)0.0023 (10)0.0277 (10)−0.0041 (10)
C160.0710 (15)0.096 (2)0.0869 (18)−0.0005 (14)0.0187 (13)0.0136 (16)
C170.081 (2)0.231 (5)0.101 (2)−0.001 (3)0.0002 (19)0.045 (3)
C180.074 (2)0.298 (8)0.110 (3)−0.043 (3)0.006 (2)−0.013 (4)
C190.095 (2)0.179 (4)0.133 (3)−0.061 (3)0.054 (2)−0.037 (3)
C200.094 (2)0.096 (2)0.100 (2)−0.0161 (16)0.0556 (17)−0.0029 (17)

Geometric parameters (Å, °)

S1—O11.424 (3)C16—C171.375 (5)
S1—O21.426 (2)C17—C181.341 (7)
S1—N11.6351 (19)C18—C191.346 (7)
S1—C61.762 (2)C19—C201.360 (5)
O3—C121.398 (5)C1—H10.9300
O3—C131.428 (5)C2—H20.9300
N1—C71.446 (3)C3—H30.9300
N1—C141.467 (4)C4—H40.9300
C1—C21.381 (5)C5—H50.9300
C1—C61.376 (4)C8—H80.9300
C2—C31.376 (6)C9—H90.9300
C3—C41.350 (5)C10—H100.9300
C4—C51.368 (4)C11—H110.9300
C5—C61.376 (4)C13—H13A0.9600
C7—C81.386 (4)C13—H13B0.9600
C7—C121.351 (4)C13—H13C0.9600
C8—C91.346 (5)C14—H14A0.9700
C9—C101.390 (7)C14—H14B0.9700
C10—C111.371 (8)C16—H160.9300
C11—C121.389 (6)C17—H170.9300
C14—C151.488 (4)C18—H180.9300
C15—C161.359 (3)C19—H190.9300
C15—C201.371 (4)C20—H200.9300
O1—S1—O2118.92 (12)C6—C1—H1121.00
O1—S1—N1107.03 (13)C1—C2—H2120.00
O1—S1—C6107.94 (12)C3—C2—H2120.00
O2—S1—N1107.55 (10)C2—C3—H3120.00
O2—S1—C6108.22 (11)C4—C3—H3120.00
N1—S1—C6106.57 (11)C3—C4—H4120.00
C12—O3—C13115.8 (4)C5—C4—H4120.00
S1—N1—C7116.09 (15)C4—C5—H5120.00
S1—N1—C14118.28 (17)C6—C5—H5120.00
C7—N1—C14120.7 (2)C7—C8—H8117.00
C2—C1—C6118.8 (3)C9—C8—H8117.00
C1—C2—C3120.1 (3)C8—C9—H9123.00
C2—C3—C4120.6 (3)C10—C9—H9123.00
C3—C4—C5120.1 (3)C9—C10—H10118.00
C4—C5—C6120.0 (3)C11—C10—H10118.00
S1—C6—C1119.66 (19)C10—C11—H11121.00
S1—C6—C5119.81 (19)C12—C11—H11121.00
C1—C6—C5120.4 (2)O3—C13—H13A109.00
N1—C7—C8120.2 (2)O3—C13—H13B109.00
N1—C7—C12122.5 (3)O3—C13—H13C109.00
C8—C7—C12117.3 (3)H13A—C13—H13B110.00
C7—C8—C9125.4 (3)H13A—C13—H13C109.00
C8—C9—C10114.7 (4)H13B—C13—H13C110.00
C9—C10—C11123.4 (5)N1—C14—H14A109.00
C10—C11—C12117.9 (4)N1—C14—H14B109.00
O3—C12—C7115.2 (3)C15—C14—H14A109.00
O3—C12—C11123.5 (3)C15—C14—H14B109.00
C7—C12—C11121.3 (4)H14A—C14—H14B108.00
N1—C14—C15113.9 (2)C15—C16—H16120.00
C14—C15—C16123.2 (2)C17—C16—H16120.00
C14—C15—C20119.0 (2)C16—C17—H17120.00
C16—C15—C20117.8 (2)C18—C17—H17120.00
C15—C16—C17120.4 (3)C17—C18—H18120.00
C16—C17—C18120.4 (4)C19—C18—H18120.00
C17—C18—C19120.2 (4)C18—C19—H19120.00
C18—C19—C20119.7 (4)C20—C19—H19120.00
C15—C20—C19121.4 (3)C15—C20—H20119.00
C2—C1—H1121.00C19—C20—H20119.00
O1—S1—N1—C7168.04 (17)C3—C4—C5—C60.6 (5)
O2—S1—N1—C739.19 (19)C4—C5—C6—S1−176.8 (2)
C6—S1—N1—C7−76.67 (18)C4—C5—C6—C1−1.0 (4)
O1—S1—N1—C14−36.5 (2)C12—C7—C8—C9−1.4 (5)
O2—S1—N1—C14−165.4 (2)N1—C7—C12—O33.1 (4)
C6—S1—N1—C1478.8 (2)N1—C7—C12—C11−178.2 (3)
N1—S1—C6—C1−79.3 (3)N1—C7—C8—C9177.9 (3)
O1—S1—C6—C135.3 (3)C8—C7—C12—O3−177.6 (2)
O2—S1—C6—C1165.3 (2)C8—C7—C12—C111.1 (4)
N1—S1—C6—C596.5 (2)C7—C8—C9—C10−0.6 (6)
O1—S1—C6—C5−148.8 (2)C8—C9—C10—C113.0 (7)
O2—S1—C6—C5−18.9 (3)C9—C10—C11—C12−3.3 (7)
C13—O3—C12—C119.1 (5)C10—C11—C12—O3179.7 (3)
C13—O3—C12—C7−172.2 (3)C10—C11—C12—C71.1 (5)
C7—N1—C14—C15−67.7 (3)N1—C14—C15—C16−27.6 (4)
C14—N1—C7—C12−62.3 (3)N1—C14—C15—C20154.3 (2)
S1—N1—C7—C1292.5 (3)C14—C15—C16—C17−179.2 (3)
C14—N1—C7—C8118.5 (3)C20—C15—C16—C17−1.2 (4)
S1—N1—C14—C15138.1 (2)C14—C15—C20—C19178.6 (3)
S1—N1—C7—C8−86.7 (2)C16—C15—C20—C190.4 (4)
C2—C1—C6—S1176.5 (3)C15—C16—C17—C180.9 (6)
C2—C1—C6—C50.6 (5)C16—C17—C18—C190.2 (8)
C6—C1—C2—C30.1 (6)C17—C18—C19—C20−1.0 (8)
C1—C2—C3—C4−0.5 (6)C18—C19—C20—C150.7 (6)
C2—C3—C4—C50.1 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14B···O30.972.362.972 (4)120

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5703).

References

  • Asiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246–o1247. [PMC free article] [PubMed]
  • Aziz-ur-Rehman, Sajjad, M. A., Akkurt, M., Sharif, S., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o1769. [PMC free article] [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.
  • Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem.15, 5105–5109. [PubMed]
  • Parari, M. K., Panda, G., Srivastava, K. & Puri, S. K. (2008). Bioorg. Med. Chem. Lett.18, 776–781. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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