N-(2-Acetyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(13)NO(3)S, the phenyl ring makes a dihedral angle of 81.5 (1)° with the benzene ring. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond and weak C-H⋯O inter-actions. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

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 = 275.31

Triclinic,

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 (; 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[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 ▶); 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.

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

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	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

	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

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) ; (ii) . Cg1 is the centroid of the benzene C7–C12 ring.