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Acta Cryst. (2009). E65, o2241    [ doi:10.1107/S1600536809033273 ]

N-(2-Acetylphenyl)benzenesulfonamide

R. R. Saravanan, V. Dhayalan, A. K. Mohanakrishnan, G. Chakkaravarthi and V. Manivannan

Abstract top

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...[pi] interactions.

Comment top

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).

Related literature top

For the biological activity of benzenesulfonamide derivatives, see: Badr (2008); Hanafy et al. (2007); Yang et al. (2002). For related structures, see: Chakkaravarthi et al. (2007); Li & Yang (2006). For graph-set notation, see: Bernstein et al. (1995). Cg1 is the centroid of the benzene C7–C12 ring.

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
N-(2-Acetylphenyl)benzenesulfonamide top
Crystal data top
C14H13NO3SZ = 2
Mr = 275.31F(000) = 288
Triclinic, P1Dx = 1.414 Mg m−3
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 mm−1
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 top
Bruker Kappa APEX2
diffractometer		5104 independent reflections
Radiation source: fine-focus sealed tube3886 reflections with I > 2σ(I)
graphiteRint = 0.023
ω and φ 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 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.41 e Å−3
Crystal data top
C14H13NO3Sγ = 83.424 (2)°
Mr = 275.31V = 646.79 (5) Å3
Triclinic, P1Z = 2
a = 7.9909 (3) ÅMo Kα radiation
b = 8.6860 (4) ŵ = 0.25 mm−1
c = 10.0701 (4) ÅT = 295 K
α = 88.016 (2)°0.24 × 0.20 × 0.20 mm
β = 68.673 (3)°
Data collection top
Bruker Kappa APEX2
diffractometer		3886 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.023
Tmin = 0.942, Tmax = 0.951θmax = 33.6°
18690 measured reflectionsStandard reflections: 0
5104 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.142Δρmax = 0.35 e Å−3
S = 1.03Δρmin = −0.41 e Å−3
5104 reflectionsAbsolute structure: ?
173 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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