N-(4-Chloro-benzo-yl)benzene-sulfonamide.

In the crystal structure of the title compound, C(13)H(10)ClNO(3)S, the conformation of the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. The dihedral angle between the two aromatic rings is 68.6 (1)°. The mol-ecule is twisted at the S atom with a dihedral angle of 75.7 (1)° between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment; the dihedral angle between the latter and the benzoyl ring is 8.3 (2)°. In the crystal, mol-ecules are linked by N-H⋯O(S) hydrogen bonds.

Related literature

For background literature and similar structures, see: Gowda et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C13H10ClNO3S

M = 295.73

Triclinic,

a = 5.4176 (4) Å

b = 10.717 (1) Å

c = 10.980 (1) Å

α = 86.666 (9)°

β = 83.903 (9)°

γ = 81.823 (8)°

V = 626.85 (9) Å3

Z = 2

Cu Kα radiation

μ = 4.30 mm−1

T = 296 K

0.48 × 0.42 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.232, T max = 0.438

2490 measured reflections

2233 independent reflections

2058 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.152

S = 1.07

2233 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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 I, global. DOI: 10.1107/S1600536809048399/ng2687sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048399/ng2687Isup2.hkl

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

C13H10ClNO3S	Z = 2
Mr = 295.73	F(000) = 304
Triclinic, P1	Dx = 1.567 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 5.4176 (4) Å	Cell parameters from 25 reflections
b = 10.717 (1) Å	θ = 5.9–21.0°
c = 10.980 (1) Å	µ = 4.30 mm−1
α = 86.666 (9)°	T = 296 K
β = 83.903 (9)°	Rod, colourless
γ = 81.823 (8)°	0.48 × 0.42 × 0.23 mm
V = 626.85 (9) Å3

Enraf–Nonius CAD-4 diffractometer	2058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 66.9°, θmin = 4.1°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.232, Tmax = 0.438	l = −13→13
2490 measured reflections	3 standard reflections every 120 min
2233 independent reflections	intensity decay: 1.5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.1034P)2 + 0.2756P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2233 reflections	Δρmax = 0.57 e Å−3
173 parameters	Δρmin = −0.52 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.063 (5)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.5435 (4)	0.1733 (2)	0.8771 (2)	0.0411 (6)
C2	0.7400 (5)	0.0803 (3)	0.8980 (3)	0.0532 (7)
H2	0.8601	0.0939	0.9485	0.064*
C3	0.7552 (6)	−0.0338 (3)	0.8426 (3)	0.0630 (8)
H3	0.8860	−0.0976	0.8562	0.076*
C4	0.5779 (6)	−0.0531 (3)	0.7674 (3)	0.0583 (7)
H4	0.5904	−0.1295	0.7296	0.070*
C5	0.3821 (6)	0.0403 (3)	0.7480 (3)	0.0555 (7)
H5	0.2622	0.0263	0.6976	0.067*
C6	0.3620 (5)	0.1542 (3)	0.8027 (2)	0.0469 (6)
H6	0.2292	0.2171	0.7900	0.056*
C7	0.6462 (5)	0.4535 (2)	0.7460 (2)	0.0408 (6)
C8	0.7940 (4)	0.5520 (2)	0.6881 (2)	0.0387 (5)
C9	0.7425 (5)	0.5974 (3)	0.5720 (2)	0.0519 (7)
H9	0.6201	0.5657	0.5343	0.062*
C10	0.8682 (6)	0.6884 (3)	0.5111 (2)	0.0534 (7)
H10	0.8306	0.7190	0.4332	0.064*
C11	1.0517 (5)	0.7341 (2)	0.5673 (2)	0.0441 (6)
C12	1.1054 (5)	0.6914 (3)	0.6829 (3)	0.0472 (6)
H12	1.2279	0.7236	0.7201	0.057*
C13	0.9770 (5)	0.6006 (2)	0.7438 (2)	0.0426 (6)
H13	1.0125	0.5716	0.8224	0.051*
N1	0.7013 (4)	0.4043 (2)	0.8612 (2)	0.0465 (5)
H1N	0.8365	0.4200	0.8882	0.056*
O1	0.2646 (4)	0.37670 (19)	0.95259 (19)	0.0590 (6)
O2	0.6378 (5)	0.2966 (2)	1.05960 (18)	0.0655 (6)
O3	0.4823 (4)	0.41570 (18)	0.69711 (17)	0.0524 (5)
Cl1	1.21303 (15)	0.84797 (7)	0.48922 (7)	0.0649 (3)
S1	0.51961 (12)	0.31704 (6)	0.94915 (5)	0.0456 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0404 (12)	0.0423 (12)	0.0425 (13)	−0.0149 (10)	−0.0024 (10)	0.0009 (10)
C2	0.0439 (13)	0.0557 (15)	0.0621 (16)	−0.0112 (11)	−0.0109 (12)	−0.0003 (12)
C3	0.0506 (16)	0.0514 (16)	0.084 (2)	−0.0013 (13)	−0.0019 (15)	−0.0026 (15)
C4	0.0625 (17)	0.0472 (14)	0.0670 (19)	−0.0216 (13)	0.0094 (14)	−0.0117 (13)
C5	0.0557 (16)	0.0611 (17)	0.0556 (16)	−0.0258 (13)	−0.0056 (12)	−0.0081 (13)
C6	0.0426 (13)	0.0506 (14)	0.0499 (14)	−0.0117 (11)	−0.0082 (11)	−0.0012 (11)
C7	0.0434 (12)	0.0408 (12)	0.0395 (12)	−0.0072 (10)	−0.0069 (10)	−0.0038 (10)
C8	0.0381 (12)	0.0398 (12)	0.0383 (12)	−0.0042 (9)	−0.0063 (9)	−0.0011 (9)
C9	0.0573 (15)	0.0600 (16)	0.0433 (14)	−0.0180 (13)	−0.0168 (12)	0.0031 (12)
C10	0.0609 (16)	0.0624 (16)	0.0395 (13)	−0.0154 (13)	−0.0141 (11)	0.0104 (12)
C11	0.0405 (12)	0.0437 (13)	0.0462 (13)	−0.0046 (10)	0.0013 (10)	0.0000 (10)
C12	0.0408 (13)	0.0540 (14)	0.0487 (14)	−0.0125 (11)	−0.0068 (10)	−0.0003 (11)
C13	0.0410 (12)	0.0507 (14)	0.0373 (12)	−0.0086 (10)	−0.0094 (10)	0.0024 (10)
N1	0.0553 (12)	0.0473 (11)	0.0426 (12)	−0.0213 (10)	−0.0150 (9)	0.0043 (9)
O1	0.0572 (12)	0.0569 (11)	0.0598 (12)	−0.0047 (9)	0.0063 (9)	−0.0078 (9)
O2	0.0992 (17)	0.0649 (13)	0.0407 (11)	−0.0339 (12)	−0.0190 (10)	0.0066 (9)
O3	0.0527 (11)	0.0588 (11)	0.0511 (10)	−0.0204 (9)	−0.0174 (8)	0.0049 (8)
Cl1	0.0664 (5)	0.0603 (5)	0.0678 (5)	−0.0208 (3)	0.0014 (4)	0.0134 (4)
S1	0.0579 (5)	0.0457 (4)	0.0362 (4)	−0.0166 (3)	−0.0057 (3)	−0.0003 (3)

C1—C2	1.379 (4)	C8—C9	1.381 (3)
C1—C6	1.387 (4)	C8—C13	1.393 (4)
C1—S1	1.755 (2)	C9—C10	1.371 (4)
C2—C3	1.385 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.383 (4)
C3—C4	1.376 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.371 (4)
C4—C5	1.376 (5)	C11—Cl1	1.735 (3)
C4—H4	0.9300	C12—C13	1.377 (4)
C5—C6	1.377 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.653 (2)
C7—O3	1.212 (3)	N1—H1N	0.8600
C7—N1	1.387 (3)	O1—S1	1.435 (2)
C7—C8	1.488 (3)	O2—S1	1.422 (2)
C2—C1—C6	121.3 (2)	C10—C9—C8	121.3 (2)
C2—C1—S1	119.1 (2)	C10—C9—H9	119.4
C6—C1—S1	119.5 (2)	C8—C9—H9	119.4
C1—C2—C3	118.8 (3)	C9—C10—C11	118.9 (2)
C1—C2—H2	120.6	C9—C10—H10	120.5
C3—C2—H2	120.6	C11—C10—H10	120.5
C4—C3—C2	120.3 (3)	C12—C11—C10	121.0 (2)
C4—C3—H3	119.8	C12—C11—Cl1	120.2 (2)
C2—C3—H3	119.8	C10—C11—Cl1	118.8 (2)
C3—C4—C5	120.1 (3)	C11—C12—C13	119.7 (2)
C3—C4—H4	119.9	C11—C12—H12	120.2
C5—C4—H4	119.9	C13—C12—H12	120.2
C4—C5—C6	120.6 (3)	C12—C13—C8	120.2 (2)
C4—C5—H5	119.7	C12—C13—H13	119.9
C6—C5—H5	119.7	C8—C13—H13	119.9
C5—C6—C1	118.8 (3)	C7—N1—S1	123.18 (18)
C5—C6—H6	120.6	C7—N1—H1N	118.4
C1—C6—H6	120.6	S1—N1—H1N	118.4
O3—C7—N1	119.6 (2)	O2—S1—O1	119.60 (14)
O3—C7—C8	122.9 (2)	O2—S1—N1	103.57 (12)
N1—C7—C8	117.5 (2)	O1—S1—N1	109.22 (12)
C9—C8—C13	118.9 (2)	O2—S1—C1	109.18 (12)
C9—C8—C7	116.9 (2)	O1—S1—C1	108.42 (12)
C13—C8—C7	124.2 (2)	N1—S1—C1	106.02 (11)
C6—C1—C2—C3	0.4 (4)	C10—C11—C12—C13	0.7 (4)
S1—C1—C2—C3	178.9 (2)	Cl1—C11—C12—C13	−179.7 (2)
C1—C2—C3—C4	0.4 (5)	C11—C12—C13—C8	0.2 (4)
C2—C3—C4—C5	−0.8 (5)	C9—C8—C13—C12	−0.8 (4)
C3—C4—C5—C6	0.5 (5)	C7—C8—C13—C12	179.8 (2)
C4—C5—C6—C1	0.3 (4)	O3—C7—N1—S1	−12.7 (3)
C2—C1—C6—C5	−0.8 (4)	C8—C7—N1—S1	167.24 (17)
S1—C1—C6—C5	−179.2 (2)	C7—N1—S1—O2	−175.7 (2)
O3—C7—C8—C9	−1.9 (4)	C7—N1—S1—O1	−47.2 (2)
N1—C7—C8—C9	178.1 (2)	C7—N1—S1—C1	69.4 (2)
O3—C7—C8—C13	177.6 (3)	C2—C1—S1—O2	−26.5 (3)
N1—C7—C8—C13	−2.4 (4)	C6—C1—S1—O2	151.9 (2)
C13—C8—C9—C10	0.3 (4)	C2—C1—S1—O1	−158.4 (2)
C7—C8—C9—C10	179.8 (3)	C6—C1—S1—O1	20.1 (2)
C8—C9—C10—C11	0.7 (4)	C2—C1—S1—N1	84.5 (2)
C9—C10—C11—C12	−1.2 (4)	C6—C1—S1—N1	−97.1 (2)
C9—C10—C11—Cl1	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.47	3.281 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.47	3.281 (3)	158

Symmetry code: (i) .