4-Chloro-N-(2-methyl-benzo-yl)benzene-sulfonamide.

In the title compound, C(14)H(12)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 two aromatic rings are tilted relative to each other by 57.7 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming centrosymmetric dimers.

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. (2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Triclinic,

a = 6.4328 (9) Å

b = 10.343 (1) Å

c = 11.207 (1) Å

α = 78.78 (1)°

β = 73.84 (1)°

γ = 84.62 (1)°

V = 701.88 (13) Å3

Z = 2

Cu Kα radiation

μ = 3.86 mm−1

T = 299 K

0.40 × 0.15 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4317 measured reflections

2502 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.039

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.04

2502 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.76 e Å−3

Δρmin = −0.56 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/S1600536810050087/bt5427sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050087/bt5427Isup2.hkl

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

C14H12ClNO3S	Z = 2
Mr = 309.76	F(000) = 320
Triclinic, P1	Dx = 1.466 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 6.4328 (9) Å	Cell parameters from 25 reflections
b = 10.343 (1) Å	θ = 4.2–22.5°
c = 11.207 (1) Å	µ = 3.86 mm−1
α = 78.78 (1)°	T = 299 K
β = 73.84 (1)°	Rod, colourless
γ = 84.62 (1)°	0.40 × 0.15 × 0.15 mm
V = 701.88 (13) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.039
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.2°
graphite	h = −7→4
ω/2θ scans	k = −12→12
4317 measured reflections	l = −13→13
2502 independent reflections	3 standard reflections every 120 min
2283 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.1004P)2 + 0.2209P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2502 reflections	Δρmax = 0.76 e Å−3
186 parameters	Δρmin = −0.56 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: 0.038 (3)

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	0.2014 (3)	0.2235 (2)	0.92052 (19)	0.0403 (5)
C2	0.3302 (4)	0.1107 (2)	0.9031 (2)	0.0505 (5)
H2	0.4576	0.0973	0.9285	0.061*
C3	0.2687 (5)	0.0180 (2)	0.8478 (3)	0.0605 (7)
H3	0.3518	−0.0596	0.8373	0.073*
C4	0.0816 (5)	0.0425 (2)	0.8083 (2)	0.0573 (6)
C5	−0.0465 (4)	0.1555 (3)	0.8239 (3)	0.0585 (6)
H5	−0.1709	0.1703	0.7955	0.070*
C6	0.0124 (4)	0.2463 (2)	0.8821 (2)	0.0512 (6)
H6	−0.0739	0.3222	0.8955	0.061*
C7	0.4960 (3)	0.4841 (2)	0.7696 (2)	0.0429 (5)
C8	0.4849 (4)	0.6049 (2)	0.6737 (2)	0.0439 (5)
C9	0.3391 (4)	0.6163 (2)	0.6007 (2)	0.0509 (6)
C10	0.3493 (5)	0.7283 (3)	0.5067 (2)	0.0686 (8)
H10	0.2534	0.7394	0.4565	0.082*
C11	0.4987 (6)	0.8224 (3)	0.4870 (3)	0.0790 (9)
H11	0.5026	0.8959	0.4237	0.095*
C12	0.6422 (6)	0.8090 (3)	0.5598 (3)	0.0768 (9)
H12	0.7427	0.8730	0.5460	0.092*
C13	0.6361 (5)	0.7005 (3)	0.6529 (3)	0.0604 (6)
H13	0.7331	0.6907	0.7023	0.073*
C14	0.1835 (4)	0.5118 (3)	0.6165 (3)	0.0661 (7)
H14A	0.0593	0.5222	0.6857	0.079*
H14B	0.2528	0.4265	0.6336	0.079*
H14C	0.1385	0.5197	0.5405	0.079*
N1	0.3253 (3)	0.47376 (17)	0.87777 (17)	0.0434 (4)
H1N	0.229 (4)	0.532 (2)	0.883 (2)	0.052*
O1	0.0959 (3)	0.38337 (16)	1.08307 (14)	0.0554 (5)
O2	0.4730 (3)	0.29640 (17)	1.02583 (16)	0.0581 (5)
O3	0.6391 (3)	0.4000 (2)	0.75586 (18)	0.0674 (5)
Cl1	0.00535 (19)	−0.07131 (8)	0.73539 (8)	0.0981 (4)
S1	0.27927 (8)	0.34281 (5)	0.99049 (5)	0.0427 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0376 (10)	0.0380 (10)	0.0435 (10)	−0.0018 (8)	−0.0103 (8)	−0.0029 (8)
C2	0.0508 (12)	0.0421 (11)	0.0553 (13)	0.0059 (9)	−0.0157 (10)	−0.0023 (9)
C3	0.0726 (17)	0.0405 (12)	0.0620 (15)	0.0046 (11)	−0.0101 (13)	−0.0089 (10)
C4	0.0726 (16)	0.0482 (13)	0.0489 (13)	−0.0211 (11)	−0.0081 (11)	−0.0063 (10)
C5	0.0505 (13)	0.0616 (15)	0.0664 (15)	−0.0146 (11)	−0.0199 (12)	−0.0062 (12)
C6	0.0405 (11)	0.0467 (12)	0.0681 (14)	0.0009 (9)	−0.0176 (10)	−0.0111 (10)
C7	0.0394 (10)	0.0468 (11)	0.0468 (11)	−0.0035 (9)	−0.0170 (9)	−0.0094 (9)
C8	0.0441 (11)	0.0461 (11)	0.0410 (10)	−0.0014 (9)	−0.0094 (9)	−0.0094 (8)
C9	0.0502 (12)	0.0609 (13)	0.0424 (11)	0.0084 (10)	−0.0136 (9)	−0.0144 (10)
C10	0.0818 (19)	0.0769 (18)	0.0469 (13)	0.0194 (15)	−0.0237 (13)	−0.0114 (12)
C11	0.112 (3)	0.0580 (16)	0.0533 (15)	0.0025 (16)	−0.0111 (16)	0.0036 (12)
C12	0.101 (2)	0.0567 (15)	0.0668 (17)	−0.0248 (15)	−0.0129 (17)	0.0003 (13)
C13	0.0670 (16)	0.0575 (14)	0.0588 (14)	−0.0147 (12)	−0.0176 (12)	−0.0082 (11)
C14	0.0479 (13)	0.095 (2)	0.0652 (16)	−0.0053 (13)	−0.0244 (12)	−0.0223 (14)
N1	0.0451 (10)	0.0387 (9)	0.0464 (10)	0.0006 (7)	−0.0129 (8)	−0.0073 (7)
O1	0.0640 (10)	0.0536 (9)	0.0427 (8)	0.0038 (8)	−0.0078 (7)	−0.0068 (7)
O2	0.0553 (10)	0.0641 (10)	0.0617 (10)	−0.0003 (8)	−0.0330 (8)	−0.0027 (8)
O3	0.0527 (10)	0.0709 (11)	0.0668 (11)	0.0169 (9)	−0.0106 (9)	−0.0015 (9)
Cl1	0.1417 (9)	0.0778 (6)	0.0845 (6)	−0.0445 (5)	−0.0243 (6)	−0.0269 (4)
S1	0.0446 (4)	0.0425 (4)	0.0418 (3)	0.0002 (2)	−0.0153 (2)	−0.0046 (2)

C1—C2	1.379 (3)	C9—C10	1.399 (4)
C1—C6	1.385 (3)	C9—C14	1.493 (4)
C1—S1	1.760 (2)	C10—C11	1.376 (5)
C2—C3	1.378 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.373 (5)
C3—C4	1.381 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.371 (4)
C4—C5	1.377 (4)	C12—H12	0.9300
C4—Cl1	1.732 (2)	C13—H13	0.9300
C5—C6	1.376 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.205 (3)	N1—S1	1.6489 (18)
C7—N1	1.385 (3)	N1—H1N	0.819 (17)
C7—C8	1.491 (3)	O1—S1	1.4280 (17)
C8—C9	1.389 (3)	O2—S1	1.4243 (17)
C8—C13	1.394 (3)
C2—C1—C6	121.3 (2)	C11—C10—C9	121.2 (3)
C2—C1—S1	119.81 (17)	C11—C10—H10	119.4
C6—C1—S1	118.90 (17)	C9—C10—H10	119.4
C3—C2—C1	119.5 (2)	C12—C11—C10	120.7 (3)
C3—C2—H2	120.3	C12—C11—H11	119.7
C1—C2—H2	120.3	C10—C11—H11	119.7
C2—C3—C4	118.8 (2)	C13—C12—C11	119.5 (3)
C2—C3—H3	120.6	C13—C12—H12	120.2
C4—C3—H3	120.6	C11—C12—H12	120.2
C5—C4—C3	122.1 (2)	C12—C13—C8	120.2 (3)
C5—C4—Cl1	118.6 (2)	C12—C13—H13	119.9
C3—C4—Cl1	119.3 (2)	C8—C13—H13	119.9
C6—C5—C4	119.0 (2)	C9—C14—H14A	109.5
C6—C5—H5	120.5	C9—C14—H14B	109.5
C4—C5—H5	120.5	H14A—C14—H14B	109.5
C5—C6—C1	119.3 (2)	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C1—C6—H6	120.3	H14B—C14—H14C	109.5
O3—C7—N1	121.3 (2)	C7—N1—S1	125.08 (16)
O3—C7—C8	123.9 (2)	C7—N1—H1N	118.8 (19)
N1—C7—C8	114.76 (18)	S1—N1—H1N	115.6 (19)
C9—C8—C13	121.2 (2)	O2—S1—O1	119.23 (11)
C9—C8—C7	120.7 (2)	O2—S1—N1	110.43 (10)
C13—C8—C7	118.0 (2)	O1—S1—N1	103.74 (10)
C8—C9—C10	117.2 (2)	O2—S1—C1	108.92 (10)
C8—C9—C14	122.2 (2)	O1—S1—C1	109.13 (11)
C10—C9—C14	120.5 (2)	N1—S1—C1	104.33 (9)
C6—C1—C2—C3	−0.8 (4)	C8—C9—C10—C11	0.5 (4)
S1—C1—C2—C3	−179.73 (18)	C14—C9—C10—C11	−176.9 (3)
C1—C2—C3—C4	1.6 (4)	C9—C10—C11—C12	−0.2 (5)
C2—C3—C4—C5	−0.8 (4)	C10—C11—C12—C13	0.0 (5)
C2—C3—C4—Cl1	178.54 (18)	C11—C12—C13—C8	−0.2 (5)
C3—C4—C5—C6	−0.8 (4)	C9—C8—C13—C12	0.5 (4)
Cl1—C4—C5—C6	179.78 (19)	C7—C8—C13—C12	175.5 (2)
C4—C5—C6—C1	1.7 (4)	O3—C7—N1—S1	−7.6 (3)
C2—C1—C6—C5	−0.9 (4)	C8—C7—N1—S1	171.71 (15)
S1—C1—C6—C5	178.06 (18)	C7—N1—S1—O2	47.7 (2)
O3—C7—C8—C9	105.2 (3)	C7—N1—S1—O1	176.59 (17)
N1—C7—C8—C9	−74.1 (3)	C7—N1—S1—C1	−69.16 (19)
O3—C7—C8—C13	−69.9 (3)	C2—C1—S1—O2	−3.0 (2)
N1—C7—C8—C13	110.9 (2)	C6—C1—S1—O2	178.07 (18)
C13—C8—C9—C10	−0.7 (3)	C2—C1—S1—O1	−134.65 (18)
C7—C8—C9—C10	−175.5 (2)	C6—C1—S1—O1	46.4 (2)
C13—C8—C9—C14	176.7 (2)	C2—C1—S1—N1	114.98 (19)
C7—C8—C9—C14	1.8 (3)	C6—C1—S1—N1	−64.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.15 (2)	2.925 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.15 (2)	2.925 (3)	157 (3)

Symmetry code: (i) .