N-(2-Acetyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809033273

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2241

doi:10.1107/S1600536809033273

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N-(2-Acetylphenyl)benzenesulfonamide

R. R. Saravanan,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^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

(Received 19 August 2009; accepted 20 August 2009; online 26 August 2009)

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 ); 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

C₁₄H₁₃NO₃S
M_r = 275.31
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.142
S = 1.03
5104 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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. Cg1 is the centroid of the benzene C7–C12 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: 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

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

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

checkCIF report

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.

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

	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.

N-(2-Acetylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₃NO₃S	Z = 2
M_r = 275.31	F(000) = 288
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEX2 diffractometer	5104 independent reflections
Radiation source: fine-focus sealed tube	3886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 33.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.942, T_max = 0.951	k = −13→13
18690 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0792P)² + 0.0784P] where P = (F_o² + 2F_c²)/3
5104 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₃NO₃S	γ = 83.424 (2)°
M_r = 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)°

Data collection top

Bruker Kappa APEX2 diffractometer	5104 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3886 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.951	R_int = 0.023
18690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
5104 reflections	Δρ_min = −0.41 e Å⁻³
173 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.942, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	18690, 5104, 3886
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.41

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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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