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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2241.
Published online 2009 August 26. doi:  10.1107/S1600536809033273
PMCID: PMC2970053

N-(2-Acetyl­phen­yl)benzene­sulfonamide

Abstract

In the title compound, C14H13NO3S, the phenyl ring makes a dihedral angle of 81.5 (1)° with the benzene ring. The mol­ecular structure is stabilized by an intra­molecular N—H(...)O hydrogen bond and weak C—H(...)O inter­actions. In the crystal structure, mol­ecules are linked by weak inter­molecular C—H(...)O and C—H(...)π inter­actions.

Related literature

For the biological activity of benzene­sulfonamide derivatives, see: Badr (2008 [triangle]); Hanafy et al. (2007 [triangle]); Yang et al. (2002 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle]); Li & Yang (2006 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-65-o2241-scheme1.jpg

Experimental

Crystal data

  • C14H13NO3S
  • M r = 275.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2241-efi1.jpg
  • a = 7.9909 (3) Å
  • b = 8.6860 (4) Å
  • c = 10.0701 (4) Å
  • α = 88.016 (2)°
  • β = 68.673 (3)°
  • γ = 83.424 (2)°
  • V = 646.79 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 295 K
  • 0.24 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.942, T max = 0.951
  • 18690 measured reflections
  • 5104 independent reflections
  • 3886 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.142
  • S = 1.03
  • 5104 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033273/is2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033273/is2453Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge IIT, Madras for the data collection.

supplementary crystallographic information

Comment

The benzenesulfonamide derivatives are known to exhibit antitumor (Yang et al., 2002), anti-bacterial (Badr, 2008) and anti-fungal (Hanafy et al., 2007) activities. The geometric parameters in (I) (Fig. 1) agree with the reported values of similar structures (Chakkaravarthi et al., 2007; Li & Yang, 2006).

The phenyl ring C1—C6 makes the dihedral angle of 81.5 (1)° with the benzene ring C7—C12. A distorted tetrahedral geometry [O1—S1—N1 109.49 (6)° and O2—S1—N1 104.32 (6)°] is observed around the S1 atom. The molecular structure is stabilized by weak intramolecular C—H···O and N—H···O interactions and the molecules are linked by weak intermolecular C—H···O and C—H···π interactions (Fig. 2 & Table 1). The intramolecular N1—H1···O3 interaction generates a six-membered ring, with graph-set motif S(6) and the intermolecular C11—H11···O1 interaction generates a fourteen membered ring, with graph-set motif R22(14).

Experimental

To a stirred solution of 1-(2-aminophenyl)ethanone (3.0 g, 22.19 mmol) in dry DCM (50 ml) at room temperature, pyridine (1.75 g, 22.12 mmol) was slowly added. After 10 min, PhSO2Cl (4.71 g, 26.61 mmol) was added and stirred at room temperature for 15 h. Then the reaction mixture was poured over crushed ice containing conc. HCl (10 ml), work up of the reaction followed by recrystallization from CDCl3 gave the compound.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, N—H = 0.86 Å and Uiso(H) = 1.2Ueq(C) for N—H, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C14H13NO3SZ = 2
Mr = 275.31F(000) = 288
Triclinic, P1Dx = 1.414 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9909 (3) ÅCell parameters from 8349 reflections
b = 8.6860 (4) Åθ = 2.2–33.4°
c = 10.0701 (4) ŵ = 0.25 mm1
α = 88.016 (2)°T = 295 K
β = 68.673 (3)°Block, colourless
γ = 83.424 (2)°0.24 × 0.20 × 0.20 mm
V = 646.79 (5) Å3

Data collection

Bruker Kappa APEX2 diffractometer5104 independent reflections
Radiation source: fine-focus sealed tube3886 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and [var phi] scansθmax = 33.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.942, Tmax = 0.951k = −13→13
18690 measured reflectionsl = −15→15

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0792P)2 + 0.0784P] where P = (Fo2 + 2Fc2)/3
5104 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.41 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.21195 (4)0.73664 (3)−0.31916 (3)0.04029 (10)
O10.07767 (14)0.86458 (13)−0.26435 (13)0.0585 (3)
O20.21545 (16)0.65492 (13)−0.44094 (11)0.0551 (3)
O30.3126 (2)0.31720 (13)−0.18266 (13)0.0665 (3)
N10.18906 (16)0.60455 (13)−0.19706 (11)0.0434 (2)
H10.17260.5138−0.21810.052*
C10.42453 (17)0.80008 (14)−0.35373 (12)0.0382 (2)
C20.4361 (2)0.95013 (16)−0.31914 (15)0.0486 (3)
H20.33241.0179−0.27620.058*
C30.6061 (3)0.9970 (2)−0.35014 (18)0.0661 (5)
H30.61751.0975−0.32820.079*
C40.7578 (3)0.8955 (3)−0.4131 (2)0.0755 (6)
H40.87140.9279−0.43340.091*
C50.7442 (2)0.7457 (3)−0.4469 (2)0.0717 (5)
H50.84810.6780−0.48930.086*
C60.5762 (2)0.69662 (19)−0.41754 (16)0.0528 (3)
H60.56530.5963−0.44010.063*
C70.19359 (15)0.62435 (14)−0.06059 (12)0.0378 (2)
C80.24861 (16)0.49460 (15)0.00745 (12)0.0396 (2)
C90.2463 (2)0.51504 (19)0.14513 (14)0.0522 (3)
H90.28180.43040.19160.063*
C100.1932 (2)0.6560 (2)0.21426 (16)0.0603 (4)
H100.19270.66620.30600.072*
C110.1410 (2)0.7816 (2)0.14616 (17)0.0626 (4)
H110.10610.87760.19200.075*
C120.1396 (2)0.76713 (18)0.01025 (16)0.0523 (3)
H120.10250.8529−0.03410.063*
C130.30558 (19)0.34007 (16)−0.06119 (15)0.0468 (3)
C140.3558 (3)0.2063 (2)0.0194 (2)0.0679 (5)
H14A0.38610.1139−0.03800.102*
H14B0.25570.19240.10590.102*
H14C0.45810.22650.04200.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.04233 (17)0.04223 (16)0.04242 (17)−0.00101 (11)−0.02377 (13)0.00144 (11)
O10.0481 (5)0.0583 (6)0.0696 (7)0.0125 (4)−0.0272 (5)0.0008 (5)
O20.0710 (7)0.0605 (6)0.0490 (5)−0.0116 (5)−0.0384 (5)0.0009 (4)
O30.1044 (10)0.0446 (5)0.0568 (6)−0.0009 (6)−0.0384 (6)−0.0043 (4)
N10.0550 (6)0.0410 (5)0.0411 (5)−0.0103 (4)−0.0243 (5)0.0022 (4)
C10.0429 (6)0.0398 (5)0.0355 (5)−0.0036 (4)−0.0189 (4)0.0031 (4)
C20.0650 (8)0.0437 (6)0.0444 (6)−0.0105 (6)−0.0276 (6)0.0039 (5)
C30.0859 (12)0.0725 (10)0.0590 (9)−0.0414 (10)−0.0410 (9)0.0211 (8)
C40.0614 (10)0.1176 (17)0.0625 (10)−0.0449 (11)−0.0334 (8)0.0380 (11)
C50.0411 (7)0.1059 (15)0.0622 (10)−0.0024 (8)−0.0149 (7)0.0170 (10)
C60.0467 (7)0.0562 (8)0.0530 (7)0.0033 (6)−0.0174 (6)−0.0028 (6)
C70.0331 (5)0.0453 (6)0.0352 (5)−0.0070 (4)−0.0118 (4)0.0001 (4)
C80.0355 (5)0.0482 (6)0.0352 (5)−0.0092 (4)−0.0119 (4)0.0043 (4)
C90.0548 (8)0.0672 (9)0.0376 (6)−0.0123 (7)−0.0193 (5)0.0081 (6)
C100.0634 (9)0.0818 (11)0.0365 (6)−0.0114 (8)−0.0174 (6)−0.0065 (7)
C110.0681 (10)0.0686 (10)0.0477 (8)0.0010 (8)−0.0175 (7)−0.0198 (7)
C120.0559 (8)0.0520 (7)0.0486 (7)0.0032 (6)−0.0202 (6)−0.0078 (6)
C130.0494 (7)0.0433 (6)0.0473 (7)−0.0069 (5)−0.0171 (5)0.0061 (5)
C140.0797 (12)0.0559 (9)0.0628 (10)0.0037 (8)−0.0240 (8)0.0138 (7)

Geometric parameters (Å, °)

S1—O11.4246 (11)C6—H60.9300
S1—O21.4280 (10)C7—C121.3957 (19)
S1—N11.6274 (11)C7—C81.4090 (17)
S1—C11.7555 (13)C8—C91.3969 (17)
O3—C131.2260 (17)C8—C131.4772 (19)
N1—C71.4049 (15)C9—C101.374 (2)
N1—H10.8597C9—H90.9300
C1—C21.3824 (18)C10—C111.374 (3)
C1—C61.3834 (19)C10—H100.9300
C2—C31.385 (2)C11—C121.383 (2)
C2—H20.9300C11—H110.9300
C3—C41.373 (3)C12—H120.9300
C3—H30.9300C13—C141.495 (2)
C4—C51.382 (3)C14—H14A0.9600
C4—H40.9300C14—H14B0.9600
C5—C61.380 (2)C14—H14C0.9600
C5—H50.9300
O1—S1—O2118.85 (7)C12—C7—N1121.74 (12)
O1—S1—N1109.49 (6)C12—C7—C8119.64 (12)
O2—S1—N1104.32 (6)N1—C7—C8118.58 (11)
O1—S1—C1108.17 (7)C9—C8—C7117.87 (12)
O2—S1—C1109.31 (6)C9—C8—C13119.87 (12)
N1—S1—C1105.96 (6)C7—C8—C13122.26 (11)
C7—N1—S1126.34 (9)C10—C9—C8122.23 (14)
C7—N1—H1116.8C10—C9—H9118.9
S1—N1—H1116.8C8—C9—H9118.9
C2—C1—C6122.22 (13)C11—C10—C9119.21 (14)
C2—C1—S1119.85 (11)C11—C10—H10120.4
C6—C1—S1117.93 (10)C9—C10—H10120.4
C1—C2—C3118.27 (15)C10—C11—C12120.77 (15)
C1—C2—H2120.9C10—C11—H11119.6
C3—C2—H2120.9C12—C11—H11119.6
C4—C3—C2120.15 (16)C11—C12—C7120.27 (15)
C4—C3—H3119.9C11—C12—H12119.9
C2—C3—H3119.9C7—C12—H12119.9
C3—C4—C5120.96 (15)O3—C13—C8122.15 (12)
C3—C4—H4119.5O3—C13—C14118.48 (14)
C5—C4—H4119.5C8—C13—C14119.37 (13)
C6—C5—C4119.90 (18)C13—C14—H14A109.5
C6—C5—H5120.0C13—C14—H14B109.5
C4—C5—H5120.0H14A—C14—H14B109.5
C5—C6—C1118.50 (16)C13—C14—H14C109.5
C5—C6—H6120.7H14A—C14—H14C109.5
C1—C6—H6120.7H14B—C14—H14C109.5
O1—S1—N1—C7−57.47 (12)S1—N1—C7—C1229.02 (17)
O2—S1—N1—C7174.32 (11)S1—N1—C7—C8−153.13 (10)
C1—S1—N1—C758.98 (12)C12—C7—C8—C90.11 (18)
O1—S1—C1—C23.58 (12)N1—C7—C8—C9−177.78 (11)
O2—S1—C1—C2134.36 (10)C12—C7—C8—C13179.40 (12)
N1—S1—C1—C2−113.75 (10)N1—C7—C8—C131.50 (17)
O1—S1—C1—C6−175.46 (10)C7—C8—C9—C10−0.2 (2)
O2—S1—C1—C6−44.68 (12)C13—C8—C9—C10−179.52 (14)
N1—S1—C1—C667.21 (11)C8—C9—C10—C11−0.2 (2)
C6—C1—C2—C30.07 (19)C9—C10—C11—C120.7 (3)
S1—C1—C2—C3−178.93 (10)C10—C11—C12—C7−0.8 (3)
C1—C2—C3—C4−0.2 (2)N1—C7—C12—C11178.19 (13)
C2—C3—C4—C50.1 (2)C8—C7—C12—C110.4 (2)
C3—C4—C5—C60.2 (3)C9—C8—C13—O3−178.77 (14)
C4—C5—C6—C1−0.3 (2)C7—C8—C13—O32.0 (2)
C2—C1—C6—C50.2 (2)C9—C8—C13—C141.5 (2)
S1—C1—C6—C5179.21 (12)C7—C8—C13—C14−177.78 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O30.862.032.596 (2)123
C2—H2···O10.932.522.893 (2)104
C12—H12···O10.932.403.057 (2)128
C11—H11···O1i0.932.513.380 (2)156
C14—H14C···Cg1ii0.962.963.763 (2)142

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2453).

References

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  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.
  • Hanafy, A., Uno, J., Mitani, H., Kang, Y. & Mikami, Y. (2007). Jpn J. Med. Mycol.48, 47–50. [PubMed]
  • Li, G.-C. & Yang, F.-L. (2006). Acta Cryst. E62, o4205–o4206.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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  • Yang, L. M., Lin, S. J., Hsu, F. L. & Yang, T. H. (2002). Bioorg. Med. Chem. Lett.12, 1013–1015. [PubMed]

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