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

The mol-ecule of the title compound, C(13)H(12)ClNO(2)S, is bent at the S atom with a C-SO(2)-NH-C torsion angle of -54.8 (2)°. The dihedral angle between the two aromatic rings is 71.6 (1)°. An intra-molecular N-H⋯Cl hydrogen bond is observed. The crystal structure features inversion-related dimers formed by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 ▶). For our studies of the effects of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2009 ▶); Nirmala et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H12ClNO2S

M = 281.75

Monoclinic,

a = 8.661 (1) Å

b = 9.949 (1) Å

c = 15.509 (1) Å

β = 99.384 (8)°

V = 1318.5 (2) Å3

Z = 4

Cu Kα radiation

μ = 4.00 mm−1

T = 299 K

0.50 × 0.13 × 0.08 mm

Data collection

Enraf–Nonius n class="Gene">CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.240, T max = 0.741

3151 measured reflections

2351 independent reflections

1792 reflections with I > 2σ(I)

R int = 0.029

3 standard reflections every 3 min

intensity decay: 1.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.117

S = 1.03

2351 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.32 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/S1600536809053756/ci2989sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053756/ci2989Isup2.hkl

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

C13H12ClNO2S	F(000) = 584
Mr = 281.75	Dx = 1.419 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 8.661 (1) Å	θ = 6.3–21.3°
b = 9.949 (1) Å	µ = 4.00 mm−1
c = 15.509 (1) Å	T = 299 K
β = 99.384 (8)°	Needle, colourless
V = 1318.5 (2) Å3	0.50 × 0.13 × 0.08 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1792 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 67.5°, θmin = 5.3°
ω/2θ scans	h = −10→2
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
Tmin = 0.240, Tmax = 0.741	l = −18→18
3151 measured reflections	3 standard reflections every 120 min
2351 independent reflections	intensity decay: 1.6%

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) = 0.117	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.203P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.003
2351 reflections	Δρmax = 0.26 e Å−3
168 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: 0.0074 (7)

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
Cl1	0.61691 (9)	−0.13179 (7)	0.05985 (5)	0.0700 (3)
S1	1.00511 (7)	0.16393 (6)	0.10719 (4)	0.0503 (2)
O1	1.0698 (2)	0.2235 (2)	0.18850 (12)	0.0636 (5)
O2	1.1070 (2)	0.0996 (2)	0.05640 (13)	0.0656 (5)
N1	0.8841 (2)	0.0448 (2)	0.12574 (15)	0.0521 (5)
H1N	0.867 (3)	−0.009 (3)	0.0838 (19)	0.062*
C1	0.8918 (3)	0.2840 (2)	0.04327 (15)	0.0471 (6)
C2	0.8224 (3)	0.2501 (3)	−0.04057 (16)	0.0574 (7)
H2	0.8376	0.1651	−0.0627	0.069*
C3	0.7314 (4)	0.3424 (3)	−0.09075 (19)	0.0626 (7)
H3	0.6840	0.3189	−0.1469	0.075*
C4	0.7084 (4)	0.4705 (3)	−0.0596 (2)	0.0669 (8)
C5	0.7801 (4)	0.5015 (3)	0.0238 (2)	0.0827 (10)
H5	0.7666	0.5868	0.0459	0.099*
C6	0.8711 (4)	0.4099 (3)	0.07551 (19)	0.0691 (8)
H6	0.9182	0.4331	0.1318	0.083*
C7	0.7485 (3)	0.0701 (2)	0.16324 (15)	0.0460 (5)
C8	0.6155 (3)	−0.0057 (2)	0.13720 (15)	0.0505 (6)
C9	0.4813 (3)	0.0161 (3)	0.17153 (18)	0.0641 (7)
H9	0.3933	−0.0368	0.1538	0.077*
C10	0.4771 (4)	0.1159 (3)	0.23198 (19)	0.0688 (8)
H10	0.3854	0.1333	0.2539	0.083*
C11	0.6092 (4)	0.1897 (3)	0.25992 (19)	0.0660 (7)
H11	0.6073	0.2561	0.3019	0.079*
C12	0.7438 (4)	0.1671 (3)	0.22683 (17)	0.0597 (7)
H12	0.8329	0.2173	0.2472	0.072*
C13	0.6086 (5)	0.5708 (4)	−0.1163 (3)	0.1005 (12)
H13A	0.5015	0.5415	−0.1254	0.121*
H13B	0.6440	0.5777	−0.1717	0.121*
H13C	0.6166	0.6569	−0.0881	0.121*

	U11	U22	U33	U12	U13	U23
Cl1	0.0684 (5)	0.0636 (4)	0.0769 (5)	−0.0086 (3)	0.0080 (4)	−0.0160 (3)
S1	0.0432 (3)	0.0513 (4)	0.0539 (4)	−0.0004 (3)	0.0003 (2)	−0.0079 (3)
O1	0.0575 (11)	0.0704 (13)	0.0567 (11)	−0.0045 (9)	−0.0093 (8)	−0.0096 (9)
O2	0.0466 (10)	0.0718 (12)	0.0789 (13)	0.0026 (9)	0.0112 (9)	−0.0164 (11)
N1	0.0515 (11)	0.0439 (12)	0.0604 (13)	0.0025 (9)	0.0078 (10)	−0.0039 (9)
C1	0.0456 (12)	0.0466 (13)	0.0480 (13)	−0.0063 (10)	0.0048 (10)	−0.0050 (10)
C2	0.0664 (17)	0.0524 (15)	0.0499 (14)	−0.0071 (13)	−0.0012 (12)	−0.0088 (11)
C3	0.0664 (17)	0.0697 (18)	0.0486 (14)	−0.0134 (14)	0.0001 (12)	0.0021 (13)
C4	0.0685 (18)	0.0590 (17)	0.0723 (19)	−0.0021 (14)	0.0087 (15)	0.0189 (14)
C5	0.116 (3)	0.0499 (17)	0.076 (2)	0.0135 (18)	−0.0039 (18)	−0.0046 (15)
C6	0.091 (2)	0.0537 (16)	0.0577 (16)	0.0036 (15)	−0.0025 (15)	−0.0152 (13)
C7	0.0493 (13)	0.0429 (12)	0.0446 (12)	0.0071 (10)	0.0038 (10)	0.0078 (10)
C8	0.0556 (14)	0.0453 (13)	0.0479 (13)	0.0042 (11)	0.0003 (11)	0.0054 (11)
C9	0.0512 (15)	0.078 (2)	0.0612 (16)	−0.0008 (14)	0.0050 (12)	0.0063 (15)
C10	0.0616 (17)	0.086 (2)	0.0607 (17)	0.0153 (16)	0.0168 (14)	0.0080 (16)
C11	0.078 (2)	0.0641 (17)	0.0570 (16)	0.0117 (15)	0.0133 (14)	−0.0037 (14)
C12	0.0629 (16)	0.0589 (16)	0.0566 (16)	−0.0002 (13)	0.0076 (13)	−0.0083 (13)
C13	0.107 (3)	0.085 (3)	0.102 (3)	0.011 (2)	−0.005 (2)	0.034 (2)

Cl1—C8	1.737 (3)	C5—H5	0.93
S1—O1	1.4233 (18)	C6—H6	0.93
S1—O2	1.4266 (19)	C7—C8	1.381 (3)
S1—N1	1.639 (2)	C7—C12	1.385 (3)
S1—C1	1.748 (3)	C8—C9	1.373 (4)
N1—C7	1.415 (3)	C9—C10	1.370 (4)
N1—H1N	0.83 (3)	C9—H9	0.93
C1—C6	1.371 (4)	C10—C11	1.369 (4)
C1—C2	1.382 (3)	C10—H10	0.93
C2—C3	1.368 (4)	C11—C12	1.367 (4)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.388 (4)	C12—H12	0.93
C3—H3	0.93	C13—H13A	0.96
C4—C5	1.376 (4)	C13—H13B	0.96
C4—C13	1.506 (4)	C13—H13C	0.96
C5—C6	1.374 (4)
O1—S1—O2	119.12 (12)	C5—C6—H6	120.3
O1—S1—N1	108.46 (12)	C8—C7—C12	118.0 (2)
O2—S1—N1	104.08 (12)	C8—C7—N1	119.4 (2)
O1—S1—C1	108.75 (12)	C12—C7—N1	122.6 (2)
O2—S1—C1	109.52 (12)	C9—C8—C7	121.3 (2)
N1—S1—C1	106.12 (11)	C9—C8—Cl1	118.9 (2)
C7—N1—S1	122.74 (17)	C7—C8—Cl1	119.8 (2)
C7—N1—H1N	112 (2)	C10—C9—C8	119.9 (3)
S1—N1—H1N	111 (2)	C10—C9—H9	120.1
C6—C1—C2	120.2 (3)	C8—C9—H9	120.1
C6—C1—S1	120.8 (2)	C11—C10—C9	119.5 (3)
C2—C1—S1	119.0 (2)	C11—C10—H10	120.3
C3—C2—C1	119.5 (3)	C9—C10—H10	120.3
C3—C2—H2	120.2	C12—C11—C10	120.8 (3)
C1—C2—H2	120.2	C12—C11—H11	119.6
C2—C3—C4	121.4 (3)	C10—C11—H11	119.6
C2—C3—H3	119.3	C11—C12—C7	120.5 (3)
C4—C3—H3	119.3	C11—C12—H12	119.7
C5—C4—C3	117.7 (3)	C7—C12—H12	119.7
C5—C4—C13	121.9 (3)	C4—C13—H13A	109.5
C3—C4—C13	120.4 (3)	C4—C13—H13B	109.5
C6—C5—C4	121.9 (3)	H13A—C13—H13B	109.5
C6—C5—H5	119.1	C4—C13—H13C	109.5
C4—C5—H5	119.1	H13A—C13—H13C	109.5
C1—C6—C5	119.3 (3)	H13B—C13—H13C	109.5
C1—C6—H6	120.3
O1—S1—N1—C7	61.9 (2)	C2—C1—C6—C5	0.4 (4)
O2—S1—N1—C7	−170.36 (19)	S1—C1—C6—C5	−179.4 (3)
C1—S1—N1—C7	−54.8 (2)	C4—C5—C6—C1	0.2 (5)
O1—S1—C1—C6	−3.0 (3)	S1—N1—C7—C8	145.7 (2)
O2—S1—C1—C6	−134.7 (2)	S1—N1—C7—C12	−35.5 (3)
N1—S1—C1—C6	113.5 (2)	C12—C7—C8—C9	1.5 (4)
O1—S1—C1—C2	177.2 (2)	N1—C7—C8—C9	−179.6 (2)
O2—S1—C1—C2	45.5 (2)	C12—C7—C8—Cl1	−178.24 (19)
N1—S1—C1—C2	−66.3 (2)	N1—C7—C8—Cl1	0.6 (3)
C6—C1—C2—C3	−0.8 (4)	C7—C8—C9—C10	0.9 (4)
S1—C1—C2—C3	179.0 (2)	Cl1—C8—C9—C10	−179.4 (2)
C1—C2—C3—C4	0.7 (4)	C8—C9—C10—C11	−2.4 (4)
C2—C3—C4—C5	−0.2 (5)	C9—C10—C11—C12	1.5 (5)
C2—C3—C4—C13	179.6 (3)	C10—C11—C12—C7	1.0 (4)
C3—C4—C5—C6	−0.3 (5)	C8—C7—C12—C11	−2.5 (4)
C13—C4—C5—C6	180.0 (3)	N1—C7—C12—C11	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (3)	2.40 (3)	3.181 (3)	156 (3)
N1—H1N···Cl1	0.83 (3)	2.46 (3)	2.952 (2)	119 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (3)	2.40 (3)	3.181 (3)	156 (3)
N1—H1N⋯Cl1	0.83 (3)	2.46 (3)	2.952 (2)	119 (2)

Symmetry code: (i) .