N-Benzoyl-2-chloro-benzene-sulfonamide.

In the crystal structure of the title compound, C(13)H(10)ClNO(3)S, the conformation of the 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 benzene rings is 73.3 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For background to our study of the effect of ring and side-chain substituents on the crystal structures of N-aromatic sulfonamides and for similar structures, see: Gowda et al. (2009 ▶; 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C13H10ClNO3S

M = 295.73

Triclinic,

a = 8.1087 (8) Å

b = 9.3057 (9) Å

c = 9.6592 (9) Å

α = 74.841 (9)°

β = 65.790 (8)°

γ = 78.077 (9)°

V = 637.52 (11) Å3

Z = 2

Cu Kα radiation

μ = 4.23 mm−1

T = 299 K

0.55 × 0.50 × 0.45 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3081 measured reflections

2210 independent reflections

2119 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.147

S = 1.19

2210 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.66 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/S1600536810008731/ng2736sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008731/ng2736Isup2.hkl

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

C13H10ClNO3S	Z = 2
Mr = 295.73	F(000) = 304
Triclinic, P1	Dx = 1.541 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.1087 (8) Å	Cell parameters from 25 reflections
b = 9.3057 (9) Å	θ = 5.0–18.3°
c = 9.6592 (9) Å	µ = 4.23 mm−1
α = 74.841 (9)°	T = 299 K
β = 65.790 (8)°	Prism, colourless
γ = 78.077 (9)°	0.55 × 0.50 × 0.45 mm
V = 637.52 (11) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.026
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 5.0°
graphite	h = −9→3
ω/2θ scans	k = −11→11
3081 measured reflections	l = −11→11
2210 independent reflections	3 standard reflections every 120 min
2119 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0828P)2 + 0.435P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.004
2210 reflections	Δρmax = 0.68 e Å−3
176 parameters	Δρmin = −0.66 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.26198 (12)	0.56179 (10)	0.59662 (10)	0.0624 (4)
S1	−0.08065 (8)	0.36244 (7)	0.76022 (7)	0.0312 (3)
O1	−0.2217 (3)	0.2758 (3)	0.8694 (2)	0.0481 (6)
O2	−0.1288 (3)	0.5111 (2)	0.6906 (2)	0.0433 (5)
O3	0.0626 (3)	0.0405 (2)	0.7472 (3)	0.0534 (6)
N1	0.0429 (3)	0.2791 (2)	0.6135 (2)	0.0332 (5)
H1N	0.078 (4)	0.334 (3)	0.5232 (19)	0.040*
C1	0.0729 (3)	0.3602 (3)	0.8476 (3)	0.0298 (6)
C2	0.2197 (4)	0.4454 (3)	0.7766 (3)	0.0360 (6)
C3	0.3387 (4)	0.4351 (4)	0.8484 (4)	0.0462 (8)
H3	0.4368	0.4915	0.8012	0.055*
C4	0.3125 (5)	0.3420 (4)	0.9892 (4)	0.0496 (8)
H4	0.3929	0.3360	1.0374	0.059*
C5	0.1694 (5)	0.2573 (4)	1.0606 (4)	0.0481 (8)
H5	0.1529	0.1947	1.1566	0.058*
C6	0.0499 (4)	0.2655 (3)	0.9892 (3)	0.0376 (6)
H6	−0.0463	0.2072	1.0366	0.045*
C7	0.1137 (3)	0.1292 (3)	0.6266 (3)	0.0323 (6)
C8	0.2554 (4)	0.0906 (3)	0.4809 (3)	0.0319 (6)
C9	0.2557 (4)	−0.0427 (3)	0.4419 (4)	0.0482 (8)
H9	0.1671	−0.1059	0.5059	0.058*
C10	0.3871 (6)	−0.0808 (4)	0.3085 (5)	0.0642 (11)
H10	0.3846	−0.1683	0.2804	0.077*
C11	0.5221 (5)	0.0087 (5)	0.2163 (4)	0.0620 (10)
H11	0.6115	−0.0189	0.1267	0.074*
C12	0.5257 (5)	0.1395 (4)	0.2561 (4)	0.0531 (8)
H12	0.6191	0.1990	0.1946	0.064*
C13	0.3913 (4)	0.1818 (3)	0.3865 (3)	0.0392 (7)
H13	0.3915	0.2718	0.4115	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0634 (6)	0.0577 (6)	0.0523 (6)	−0.0258 (4)	−0.0168 (4)	0.0179 (4)
S1	0.0286 (4)	0.0371 (4)	0.0234 (4)	0.0013 (3)	−0.0053 (3)	−0.0100 (3)
O1	0.0312 (10)	0.0708 (15)	0.0354 (11)	−0.0156 (10)	−0.0013 (8)	−0.0106 (10)
O2	0.0486 (12)	0.0441 (12)	0.0323 (11)	0.0134 (9)	−0.0150 (9)	−0.0146 (9)
O3	0.0594 (14)	0.0387 (11)	0.0407 (12)	−0.0054 (10)	−0.0056 (10)	0.0050 (9)
N1	0.0396 (12)	0.0302 (11)	0.0245 (11)	−0.0018 (9)	−0.0072 (9)	−0.0068 (9)
C1	0.0296 (12)	0.0297 (12)	0.0261 (13)	0.0024 (10)	−0.0059 (10)	−0.0111 (10)
C2	0.0374 (14)	0.0289 (13)	0.0370 (15)	−0.0027 (10)	−0.0089 (11)	−0.0083 (11)
C3	0.0424 (16)	0.0448 (17)	0.057 (2)	−0.0060 (13)	−0.0188 (14)	−0.0184 (15)
C4	0.0502 (17)	0.0561 (19)	0.054 (2)	0.0074 (14)	−0.0298 (15)	−0.0235 (16)
C5	0.0548 (18)	0.0550 (19)	0.0315 (15)	0.0070 (15)	−0.0191 (14)	−0.0094 (14)
C6	0.0384 (14)	0.0398 (15)	0.0276 (14)	0.0008 (11)	−0.0078 (11)	−0.0067 (11)
C7	0.0353 (13)	0.0280 (12)	0.0329 (14)	−0.0057 (10)	−0.0124 (11)	−0.0038 (11)
C8	0.0364 (13)	0.0259 (12)	0.0342 (14)	0.0032 (10)	−0.0161 (11)	−0.0080 (10)
C9	0.0505 (17)	0.0339 (15)	0.066 (2)	0.0019 (13)	−0.0237 (16)	−0.0228 (15)
C10	0.070 (2)	0.058 (2)	0.081 (3)	0.0185 (18)	−0.036 (2)	−0.048 (2)
C11	0.055 (2)	0.077 (3)	0.049 (2)	0.0274 (19)	−0.0176 (16)	−0.0360 (19)
C12	0.0424 (17)	0.059 (2)	0.0432 (18)	0.0059 (14)	−0.0068 (14)	−0.0106 (15)
C13	0.0391 (14)	0.0345 (14)	0.0386 (16)	−0.0012 (11)	−0.0093 (12)	−0.0095 (12)

Cl1—C2	1.730 (3)	C5—C6	1.382 (4)
S1—O1	1.421 (2)	C5—H5	0.9300
S1—O2	1.423 (2)	C6—H6	0.9300
S1—N1	1.644 (2)	C7—C8	1.482 (4)
S1—C1	1.762 (3)	C8—C13	1.387 (4)
O3—C7	1.206 (3)	C8—C9	1.387 (4)
N1—C7	1.388 (3)	C9—C10	1.370 (5)
N1—H1N	0.853 (10)	C9—H9	0.9300
C1—C6	1.382 (4)	C10—C11	1.369 (6)
C1—C2	1.398 (4)	C10—H10	0.9300
C2—C3	1.378 (4)	C11—C12	1.378 (5)
C3—C4	1.367 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.373 (4)
C4—C5	1.371 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
O1—S1—O2	118.68 (13)	C1—C6—C5	120.2 (3)
O1—S1—N1	110.43 (12)	C1—C6—H6	119.9
O2—S1—N1	104.55 (11)	C5—C6—H6	119.9
O1—S1—C1	107.69 (13)	O3—C7—N1	121.8 (3)
O2—S1—C1	110.95 (12)	O3—C7—C8	124.1 (2)
N1—S1—C1	103.50 (12)	N1—C7—C8	114.1 (2)
C7—N1—S1	124.95 (19)	C13—C8—C9	119.5 (3)
C7—N1—H1N	117 (2)	C13—C8—C7	121.4 (2)
S1—N1—H1N	118 (2)	C9—C8—C7	119.0 (3)
C6—C1—C2	119.2 (3)	C10—C9—C8	119.7 (3)
C6—C1—S1	118.1 (2)	C10—C9—H9	120.2
C2—C1—S1	122.6 (2)	C8—C9—H9	120.2
C3—C2—C1	119.9 (3)	C11—C10—C9	120.7 (3)
C3—C2—Cl1	118.0 (2)	C11—C10—H10	119.7
C1—C2—Cl1	122.0 (2)	C9—C10—H10	119.7
C4—C3—C2	119.9 (3)	C10—C11—C12	120.1 (3)
C4—C3—H3	120.0	C10—C11—H11	120.0
C2—C3—H3	120.0	C12—C11—H11	120.0
C3—C4—C5	121.0 (3)	C13—C12—C11	119.9 (3)
C3—C4—H4	119.5	C13—C12—H12	120.0
C5—C4—H4	119.5	C11—C12—H12	120.0
C4—C5—C6	119.7 (3)	C12—C13—C8	120.1 (3)
C4—C5—H5	120.2	C12—C13—H13	120.0
C6—C5—H5	120.2	C8—C13—H13	120.0
O1—S1—N1—C7	−48.3 (3)	C2—C1—C6—C5	1.0 (4)
O2—S1—N1—C7	−177.1 (2)	S1—C1—C6—C5	178.5 (2)
C1—S1—N1—C7	66.7 (2)	C4—C5—C6—C1	−0.9 (4)
O1—S1—C1—C6	8.2 (2)	S1—N1—C7—O3	13.9 (4)
O2—S1—C1—C6	139.7 (2)	S1—N1—C7—C8	−165.87 (18)
N1—S1—C1—C6	−108.7 (2)	O3—C7—C8—C13	−136.3 (3)
O1—S1—C1—C2	−174.3 (2)	N1—C7—C8—C13	43.5 (3)
O2—S1—C1—C2	−42.9 (2)	O3—C7—C8—C9	41.1 (4)
N1—S1—C1—C2	68.7 (2)	N1—C7—C8—C9	−139.2 (3)
C6—C1—C2—C3	−0.4 (4)	C13—C8—C9—C10	−1.8 (5)
S1—C1—C2—C3	−177.8 (2)	C7—C8—C9—C10	−179.2 (3)
C6—C1—C2—Cl1	177.9 (2)	C8—C9—C10—C11	2.4 (5)
S1—C1—C2—Cl1	0.4 (3)	C9—C10—C11—C12	−0.8 (6)
C1—C2—C3—C4	−0.3 (4)	C10—C11—C12—C13	−1.5 (5)
Cl1—C2—C3—C4	−178.6 (2)	C11—C12—C13—C8	2.1 (5)
C2—C3—C4—C5	0.4 (5)	C9—C8—C13—C12	−0.5 (4)
C3—C4—C5—C6	0.2 (5)	C7—C8—C13—C12	176.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (1)	2.12 (1)	2.968 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (1)	2.12 (1)	2.968 (3)	172 (3)

Symmetry code: (i) .