N-(3-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 benzene rings is 87.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

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

Experimental

Crystal data

C13H10ClNO3S

M = 295.73

Monoclinic,

a = 21.309 (2) Å

b = 6.0953 (7) Å

c = 20.367 (2) Å

β = 92.48 (1)°

V = 2642.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 299 K

0.42 × 0.40 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.834, T max = 0.900

5328 measured reflections

2714 independent reflections

1968 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.133

S = 0.92

2714 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536809041051/pk2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041051/pk2198Isup2.hkl

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

C13H10ClNO3S	F(000) = 1216
Mr = 295.73	Dx = 1.486 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1936 reflections
a = 21.309 (2) Å	θ = 2.7–28.0°
b = 6.0953 (7) Å	µ = 0.45 mm−1
c = 20.367 (2) Å	T = 299 K
β = 92.48 (1)°	Prism, colourless
V = 2642.9 (5) Å3	0.42 × 0.40 × 0.24 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2714 independent reflections
Radiation source: fine-focus sealed tube	1968 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→16
Tmin = 0.834, Tmax = 0.900	k = −7→6
5328 measured reflections	l = −25→25

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
2714 reflections	Δρmax = 0.18 e Å−3
176 parameters	Δρmin = −0.32 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: 0.0038 (7)

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.20143 (9)	−0.0804 (3)	0.65509 (10)	0.0418 (5)
C2	0.19836 (10)	0.0558 (4)	0.70922 (10)	0.0486 (5)
H2	0.2161	0.1952	0.7087	0.058*
C3	0.16863 (13)	−0.0179 (4)	0.76404 (12)	0.0648 (7)
H3	0.1668	0.0720	0.8008	0.078*
C4	0.14182 (12)	−0.2218 (5)	0.76472 (13)	0.0687 (7)
H4	0.1218	−0.2697	0.8018	0.082*
C5	0.14450 (12)	−0.3554 (4)	0.71097 (15)	0.0696 (7)
H5	0.1257	−0.4929	0.7116	0.084*
C6	0.17497 (11)	−0.2883 (3)	0.65551 (12)	0.0569 (6)
H6	0.1776	−0.3808	0.6194	0.068*
C7	0.13356 (10)	0.1419 (3)	0.52483 (10)	0.0483 (5)
C8	0.08621 (9)	0.1089 (3)	0.46936 (10)	0.0486 (5)
C9	0.08589 (10)	−0.0686 (4)	0.42751 (10)	0.0519 (5)
H9	0.1175	−0.1737	0.4316	0.062*
C10	0.03867 (11)	−0.0901 (4)	0.37955 (10)	0.0562 (6)
C11	−0.00920 (12)	0.0610 (5)	0.37261 (13)	0.0705 (7)
H11	−0.0411	0.0440	0.3404	0.085*
C12	−0.00860 (15)	0.2364 (5)	0.41439 (18)	0.0949 (10)
H12	−0.0404	0.3407	0.4102	0.114*
C13	0.03849 (13)	0.2618 (4)	0.46282 (15)	0.0772 (8)
H13	0.0380	0.3819	0.4910	0.093*
N1	0.18539 (9)	0.0071 (3)	0.52611 (8)	0.0498 (5)
H1N	0.1947 (11)	−0.082 (4)	0.4968 (12)	0.060*
O1	0.28316 (7)	−0.1577 (3)	0.56683 (8)	0.0734 (6)
O2	0.26351 (8)	0.2263 (3)	0.59692 (7)	0.0655 (5)
O3	0.12636 (8)	0.2751 (3)	0.56792 (8)	0.0695 (5)
Cl1	0.03840 (4)	−0.31286 (16)	0.32733 (4)	0.1016 (3)
S1	0.24035 (2)	0.00980 (9)	0.58590 (2)	0.0490 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0370 (10)	0.0454 (10)	0.0420 (10)	0.0088 (9)	−0.0084 (8)	−0.0040 (8)
C2	0.0523 (12)	0.0503 (12)	0.0429 (11)	−0.0007 (9)	−0.0009 (9)	−0.0076 (9)
C3	0.0667 (16)	0.0830 (18)	0.0449 (12)	0.0055 (13)	0.0039 (11)	−0.0048 (12)
C4	0.0602 (16)	0.0855 (18)	0.0602 (15)	−0.0003 (13)	0.0010 (12)	0.0214 (14)
C5	0.0590 (15)	0.0527 (14)	0.096 (2)	−0.0034 (11)	−0.0082 (15)	0.0199 (14)
C6	0.0538 (13)	0.0464 (12)	0.0690 (15)	0.0067 (10)	−0.0144 (11)	−0.0094 (11)
C7	0.0480 (12)	0.0527 (12)	0.0437 (11)	0.0083 (10)	−0.0030 (9)	−0.0027 (9)
C8	0.0418 (11)	0.0587 (13)	0.0447 (11)	0.0093 (10)	−0.0036 (9)	−0.0001 (10)
C9	0.0435 (12)	0.0708 (14)	0.0408 (11)	0.0110 (10)	−0.0050 (9)	−0.0031 (10)
C10	0.0480 (13)	0.0786 (15)	0.0416 (11)	−0.0027 (12)	−0.0042 (9)	0.0001 (11)
C11	0.0496 (14)	0.098 (2)	0.0621 (15)	0.0053 (14)	−0.0201 (12)	0.0098 (14)
C12	0.0680 (18)	0.097 (2)	0.117 (3)	0.0362 (16)	−0.0345 (18)	−0.009 (2)
C13	0.0631 (16)	0.0783 (17)	0.0880 (18)	0.0275 (14)	−0.0211 (14)	−0.0190 (15)
N1	0.0451 (10)	0.0688 (12)	0.0348 (9)	0.0139 (8)	−0.0067 (7)	−0.0155 (8)
O1	0.0482 (9)	0.1156 (15)	0.0554 (10)	0.0295 (9)	−0.0097 (8)	−0.0298 (10)
O2	0.0635 (10)	0.0830 (11)	0.0497 (9)	−0.0240 (9)	−0.0011 (8)	−0.0036 (8)
O3	0.0721 (11)	0.0670 (10)	0.0680 (11)	0.0201 (9)	−0.0139 (9)	−0.0271 (9)
Cl1	0.0912 (6)	0.1320 (7)	0.0789 (5)	0.0054 (5)	−0.0282 (4)	−0.0466 (5)
S1	0.0378 (3)	0.0713 (4)	0.0374 (3)	0.0049 (2)	−0.0044 (2)	−0.0125 (2)

C1—C2	1.384 (3)	C8—C9	1.377 (3)
C1—C6	1.387 (3)	C8—C13	1.382 (3)
C1—S1	1.754 (2)	C9—C10	1.378 (3)
C2—C3	1.382 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.377 (4)
C3—C4	1.369 (3)	C10—Cl1	1.725 (2)
C3—H3	0.9300	C11—C12	1.366 (4)
C4—C5	1.367 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.385 (4)
C5—C6	1.389 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	N1—S1	1.6527 (18)
C7—O3	1.210 (2)	N1—H1N	0.84 (2)
C7—N1	1.376 (3)	O1—S1	1.4340 (16)
C7—C8	1.495 (3)	O2—S1	1.4232 (16)
C2—C1—C6	120.7 (2)	C8—C9—C10	119.8 (2)
C2—C1—S1	119.47 (17)	C8—C9—H9	120.1
C6—C1—S1	119.85 (16)	C10—C9—H9	120.1
C3—C2—C1	119.2 (2)	C11—C10—C9	121.6 (2)
C3—C2—H2	120.4	C11—C10—Cl1	118.72 (19)
C1—C2—H2	120.4	C9—C10—Cl1	119.64 (18)
C4—C3—C2	120.6 (2)	C12—C11—C10	118.2 (2)
C4—C3—H3	119.7	C12—C11—H11	120.9
C2—C3—H3	119.7	C10—C11—H11	120.9
C5—C4—C3	120.1 (2)	C11—C12—C13	121.2 (3)
C5—C4—H4	120.0	C11—C12—H12	119.4
C3—C4—H4	120.0	C13—C12—H12	119.4
C4—C5—C6	120.9 (2)	C8—C13—C12	120.0 (3)
C4—C5—H5	119.6	C8—C13—H13	120.0
C6—C5—H5	119.6	C12—C13—H13	120.0
C1—C6—C5	118.6 (2)	C7—N1—S1	123.41 (15)
C1—C6—H6	120.7	C7—N1—H1N	126.0 (17)
C5—C6—H6	120.7	S1—N1—H1N	110.5 (17)
O3—C7—N1	120.9 (2)	O2—S1—O1	118.86 (11)
O3—C7—C8	122.38 (19)	O2—S1—N1	110.81 (10)
N1—C7—C8	116.66 (17)	O1—S1—N1	103.42 (9)
C9—C8—C13	119.1 (2)	O2—S1—C1	109.68 (9)
C9—C8—C7	123.94 (18)	O1—S1—C1	108.83 (11)
C13—C8—C7	116.8 (2)	N1—S1—C1	104.13 (10)
C6—C1—C2—C3	0.1 (3)	Cl1—C10—C11—C12	179.8 (2)
S1—C1—C2—C3	−178.81 (18)	C10—C11—C12—C13	−0.5 (5)
C1—C2—C3—C4	−0.8 (4)	C9—C8—C13—C12	−0.5 (5)
C2—C3—C4—C5	0.3 (4)	C7—C8—C13—C12	−177.1 (3)
C3—C4—C5—C6	0.9 (4)	C11—C12—C13—C8	0.4 (5)
C2—C1—C6—C5	1.0 (3)	O3—C7—N1—S1	1.5 (3)
S1—C1—C6—C5	179.95 (17)	C8—C7—N1—S1	−176.23 (15)
C4—C5—C6—C1	−1.5 (3)	C7—N1—S1—O2	−52.6 (2)
O3—C7—C8—C9	−165.9 (2)	C7—N1—S1—O1	178.97 (19)
N1—C7—C8—C9	11.8 (3)	C7—N1—S1—C1	65.3 (2)
O3—C7—C8—C13	10.6 (4)	C2—C1—S1—O2	−0.9 (2)
N1—C7—C8—C13	−171.7 (2)	C6—C1—S1—O2	−179.87 (16)
C13—C8—C9—C10	0.7 (4)	C2—C1—S1—O1	130.64 (17)
C7—C8—C9—C10	177.1 (2)	C6—C1—S1—O1	−48.30 (19)
C8—C9—C10—C11	−0.8 (4)	C2—C1—S1—N1	−119.56 (17)
C8—C9—C10—Cl1	−179.90 (18)	C6—C1—S1—N1	61.49 (18)
C9—C10—C11—C12	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.12 (2)	2.946 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.12 (2)	2.946 (2)	171 (2)

Symmetry code: (i) .