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organic compounds
N-(2-Acetylphenyl)benzenesulfonamide
aDepartment of Physics, PRIST University, Thanjavur 614 904, Tamil Nadu, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: manivan_1999@yahoo.com
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 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); 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
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004
); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536809033273/is2453sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809033273/is2453Isup2.hkl
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.
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.
Data collection: APEX2 (Bruker, 2004); cell
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).C14H13NO3S | Z = 2 |
Mr = 275.31 | F(000) = 288 |
Triclinic, P1 | Dx = 1.414 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9909 (3) Å | Cell parameters from 8349 reflections |
b = 8.6860 (4) Å | θ = 2.2–33.4° |
c = 10.0701 (4) Å | µ = 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 |
Bruker Kappa APEX2 diffractometer | 5104 independent reflections |
Radiation source: fine-focus sealed tube | 3886 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω and ϕ scans | θmax = 33.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.942, Tmax = 0.951 | k = −13→13 |
18690 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C14H13NO3S | γ = 83.424 (2)° |
Mr = 275.31 | V = 646.79 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9909 (3) Å | Mo Kα radiation |
b = 8.6860 (4) Å | µ = 0.25 mm−1 |
c = 10.0701 (4) Å | T = 295 K |
α = 88.016 (2)° | 0.24 × 0.20 × 0.20 mm |
β = 68.673 (3)° |
Bruker Kappa APEX2 diffractometer | 5104 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3886 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.951 | Rint = 0.023 |
18690 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.35 e Å−3 |
5104 reflections | Δρmin = −0.41 e Å−3 |
173 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.21195 (4) | 0.73664 (3) | −0.31916 (3) | 0.04029 (10) | |
O1 | 0.07767 (14) | 0.86458 (13) | −0.26435 (13) | 0.0585 (3) | |
O2 | 0.21545 (16) | 0.65492 (13) | −0.44094 (11) | 0.0551 (3) | |
O3 | 0.3126 (2) | 0.31720 (13) | −0.18266 (13) | 0.0665 (3) | |
N1 | 0.18906 (16) | 0.60455 (13) | −0.19706 (11) | 0.0434 (2) | |
H1 | 0.1726 | 0.5138 | −0.2181 | 0.052* | |
C1 | 0.42453 (17) | 0.80008 (14) | −0.35373 (12) | 0.0382 (2) | |
C2 | 0.4361 (2) | 0.95013 (16) | −0.31914 (15) | 0.0486 (3) | |
H2 | 0.3324 | 1.0179 | −0.2762 | 0.058* | |
C3 | 0.6061 (3) | 0.9970 (2) | −0.35014 (18) | 0.0661 (5) | |
H3 | 0.6175 | 1.0975 | −0.3282 | 0.079* | |
C4 | 0.7578 (3) | 0.8955 (3) | −0.4131 (2) | 0.0755 (6) | |
H4 | 0.8714 | 0.9279 | −0.4334 | 0.091* | |
C5 | 0.7442 (2) | 0.7457 (3) | −0.4469 (2) | 0.0717 (5) | |
H5 | 0.8481 | 0.6780 | −0.4893 | 0.086* | |
C6 | 0.5762 (2) | 0.69662 (19) | −0.41754 (16) | 0.0528 (3) | |
H6 | 0.5653 | 0.5963 | −0.4401 | 0.063* | |
C7 | 0.19359 (15) | 0.62435 (14) | −0.06059 (12) | 0.0378 (2) | |
C8 | 0.24861 (16) | 0.49460 (15) | 0.00745 (12) | 0.0396 (2) | |
C9 | 0.2463 (2) | 0.51504 (19) | 0.14513 (14) | 0.0522 (3) | |
H9 | 0.2818 | 0.4304 | 0.1916 | 0.063* | |
C10 | 0.1932 (2) | 0.6560 (2) | 0.21426 (16) | 0.0603 (4) | |
H10 | 0.1927 | 0.6662 | 0.3060 | 0.072* | |
C11 | 0.1410 (2) | 0.7816 (2) | 0.14616 (17) | 0.0626 (4) | |
H11 | 0.1061 | 0.8776 | 0.1920 | 0.075* | |
C12 | 0.1396 (2) | 0.76713 (18) | 0.01025 (16) | 0.0523 (3) | |
H12 | 0.1025 | 0.8529 | −0.0341 | 0.063* | |
C13 | 0.30558 (19) | 0.34007 (16) | −0.06119 (15) | 0.0468 (3) | |
C14 | 0.3558 (3) | 0.2063 (2) | 0.0194 (2) | 0.0679 (5) | |
H14A | 0.3861 | 0.1139 | −0.0380 | 0.102* | |
H14B | 0.2557 | 0.1924 | 0.1059 | 0.102* | |
H14C | 0.4581 | 0.2265 | 0.0420 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04233 (17) | 0.04223 (16) | 0.04242 (17) | −0.00101 (11) | −0.02377 (13) | 0.00144 (11) |
O1 | 0.0481 (5) | 0.0583 (6) | 0.0696 (7) | 0.0125 (4) | −0.0272 (5) | 0.0008 (5) |
O2 | 0.0710 (7) | 0.0605 (6) | 0.0490 (5) | −0.0116 (5) | −0.0384 (5) | 0.0009 (4) |
O3 | 0.1044 (10) | 0.0446 (5) | 0.0568 (6) | −0.0009 (6) | −0.0384 (6) | −0.0043 (4) |
N1 | 0.0550 (6) | 0.0410 (5) | 0.0411 (5) | −0.0103 (4) | −0.0243 (5) | 0.0022 (4) |
C1 | 0.0429 (6) | 0.0398 (5) | 0.0355 (5) | −0.0036 (4) | −0.0189 (4) | 0.0031 (4) |
C2 | 0.0650 (8) | 0.0437 (6) | 0.0444 (6) | −0.0105 (6) | −0.0276 (6) | 0.0039 (5) |
C3 | 0.0859 (12) | 0.0725 (10) | 0.0590 (9) | −0.0414 (10) | −0.0410 (9) | 0.0211 (8) |
C4 | 0.0614 (10) | 0.1176 (17) | 0.0625 (10) | −0.0449 (11) | −0.0334 (8) | 0.0380 (11) |
C5 | 0.0411 (7) | 0.1059 (15) | 0.0622 (10) | −0.0024 (8) | −0.0149 (7) | 0.0170 (10) |
C6 | 0.0467 (7) | 0.0562 (8) | 0.0530 (7) | 0.0033 (6) | −0.0174 (6) | −0.0028 (6) |
C7 | 0.0331 (5) | 0.0453 (6) | 0.0352 (5) | −0.0070 (4) | −0.0118 (4) | 0.0001 (4) |
C8 | 0.0355 (5) | 0.0482 (6) | 0.0352 (5) | −0.0092 (4) | −0.0119 (4) | 0.0043 (4) |
C9 | 0.0548 (8) | 0.0672 (9) | 0.0376 (6) | −0.0123 (7) | −0.0193 (5) | 0.0081 (6) |
C10 | 0.0634 (9) | 0.0818 (11) | 0.0365 (6) | −0.0114 (8) | −0.0174 (6) | −0.0065 (7) |
C11 | 0.0681 (10) | 0.0686 (10) | 0.0477 (8) | 0.0010 (8) | −0.0175 (7) | −0.0198 (7) |
C12 | 0.0559 (8) | 0.0520 (7) | 0.0486 (7) | 0.0032 (6) | −0.0202 (6) | −0.0078 (6) |
C13 | 0.0494 (7) | 0.0433 (6) | 0.0473 (7) | −0.0069 (5) | −0.0171 (5) | 0.0061 (5) |
C14 | 0.0797 (12) | 0.0559 (9) | 0.0628 (10) | 0.0037 (8) | −0.0240 (8) | 0.0138 (7) |
S1—O1 | 1.4246 (11) | C6—H6 | 0.9300 |
S1—O2 | 1.4280 (10) | C7—C12 | 1.3957 (19) |
S1—N1 | 1.6274 (11) | C7—C8 | 1.4090 (17) |
S1—C1 | 1.7555 (13) | C8—C9 | 1.3969 (17) |
O3—C13 | 1.2260 (17) | C8—C13 | 1.4772 (19) |
N1—C7 | 1.4049 (15) | C9—C10 | 1.374 (2) |
N1—H1 | 0.8597 | C9—H9 | 0.9300 |
C1—C2 | 1.3824 (18) | C10—C11 | 1.374 (3) |
C1—C6 | 1.3834 (19) | C10—H10 | 0.9300 |
C2—C3 | 1.385 (2) | C11—C12 | 1.383 (2) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.373 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.495 (2) |
C4—C5 | 1.382 (3) | C14—H14A | 0.9600 |
C4—H4 | 0.9300 | C14—H14B | 0.9600 |
C5—C6 | 1.380 (2) | C14—H14C | 0.9600 |
C5—H5 | 0.9300 | ||
O1—S1—O2 | 118.85 (7) | C12—C7—N1 | 121.74 (12) |
O1—S1—N1 | 109.49 (6) | C12—C7—C8 | 119.64 (12) |
O2—S1—N1 | 104.32 (6) | N1—C7—C8 | 118.58 (11) |
O1—S1—C1 | 108.17 (7) | C9—C8—C7 | 117.87 (12) |
O2—S1—C1 | 109.31 (6) | C9—C8—C13 | 119.87 (12) |
N1—S1—C1 | 105.96 (6) | C7—C8—C13 | 122.26 (11) |
C7—N1—S1 | 126.34 (9) | C10—C9—C8 | 122.23 (14) |
C7—N1—H1 | 116.8 | C10—C9—H9 | 118.9 |
S1—N1—H1 | 116.8 | C8—C9—H9 | 118.9 |
C2—C1—C6 | 122.22 (13) | C11—C10—C9 | 119.21 (14) |
C2—C1—S1 | 119.85 (11) | C11—C10—H10 | 120.4 |
C6—C1—S1 | 117.93 (10) | C9—C10—H10 | 120.4 |
C1—C2—C3 | 118.27 (15) | C10—C11—C12 | 120.77 (15) |
C1—C2—H2 | 120.9 | C10—C11—H11 | 119.6 |
C3—C2—H2 | 120.9 | C12—C11—H11 | 119.6 |
C4—C3—C2 | 120.15 (16) | C11—C12—C7 | 120.27 (15) |
C4—C3—H3 | 119.9 | C11—C12—H12 | 119.9 |
C2—C3—H3 | 119.9 | C7—C12—H12 | 119.9 |
C3—C4—C5 | 120.96 (15) | O3—C13—C8 | 122.15 (12) |
C3—C4—H4 | 119.5 | O3—C13—C14 | 118.48 (14) |
C5—C4—H4 | 119.5 | C8—C13—C14 | 119.37 (13) |
C6—C5—C4 | 119.90 (18) | C13—C14—H14A | 109.5 |
C6—C5—H5 | 120.0 | C13—C14—H14B | 109.5 |
C4—C5—H5 | 120.0 | H14A—C14—H14B | 109.5 |
C5—C6—C1 | 118.50 (16) | C13—C14—H14C | 109.5 |
C5—C6—H6 | 120.7 | H14A—C14—H14C | 109.5 |
C1—C6—H6 | 120.7 | H14B—C14—H14C | 109.5 |
O1—S1—N1—C7 | −57.47 (12) | S1—N1—C7—C12 | 29.02 (17) |
O2—S1—N1—C7 | 174.32 (11) | S1—N1—C7—C8 | −153.13 (10) |
C1—S1—N1—C7 | 58.98 (12) | C12—C7—C8—C9 | 0.11 (18) |
O1—S1—C1—C2 | 3.58 (12) | N1—C7—C8—C9 | −177.78 (11) |
O2—S1—C1—C2 | 134.36 (10) | C12—C7—C8—C13 | 179.40 (12) |
N1—S1—C1—C2 | −113.75 (10) | N1—C7—C8—C13 | 1.50 (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—C6 | 67.21 (11) | C8—C9—C10—C11 | −0.2 (2) |
C6—C1—C2—C3 | 0.07 (19) | C9—C10—C11—C12 | 0.7 (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—C11 | 178.19 (13) |
C2—C3—C4—C5 | 0.1 (2) | C8—C7—C12—C11 | 0.4 (2) |
C3—C4—C5—C6 | 0.2 (3) | C9—C8—C13—O3 | −178.77 (14) |
C4—C5—C6—C1 | −0.3 (2) | C7—C8—C13—O3 | 2.0 (2) |
C2—C1—C6—C5 | 0.2 (2) | C9—C8—C13—C14 | 1.5 (2) |
S1—C1—C6—C5 | 179.21 (12) | C7—C8—C13—C14 | −177.78 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.03 | 2.596 (2) | 123 |
C2—H2···O1 | 0.93 | 2.52 | 2.893 (2) | 104 |
C12—H12···O1 | 0.93 | 2.40 | 3.057 (2) | 128 |
C11—H11···O1i | 0.93 | 2.51 | 3.380 (2) | 156 |
C14—H14C···Cg1ii | 0.96 | 2.96 | 3.763 (2) | 142 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C14H13NO3S |
Mr | 275.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 7.9909 (3), 8.6860 (4), 10.0701 (4) |
α, β, γ (°) | 88.016 (2), 68.673 (3), 83.424 (2) |
V (Å3) | 646.79 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.24 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEX2 diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.942, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18690, 5104, 3886 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.779 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.142, 1.03 |
No. of reflections | 5104 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.41 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.03 | 2.596 (2) | 123 |
C2—H2···O1 | 0.93 | 2.52 | 2.893 (2) | 104 |
C12—H12···O1 | 0.93 | 2.40 | 3.057 (2) | 128 |
C11—H11···O1i | 0.93 | 2.51 | 3.380 (2) | 156 |
C14—H14C···Cg1ii | 0.96 | 2.96 | 3.763 (2) | 142 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+1, −z. |
Acknowledgements
The authors wish to acknowledge IIT, Madras for the data collection.
References
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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).