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

In the title compound, C(14)H(12)ClNO(3)S, the C=O bond is syn to the Cl substituent in the adjacent benzene ring. The C-S-N-C torsion angle is -80.6 (6)°. The chloro-benzoyl ring is disordered and was refined using a split model [occupancy ratio 0.537 (3):0.463 (3)]. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming inversion dimers.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶, 2007 ▶), of N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Gowda et al. (2010 ▶), of N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Monoclinic,

a = 25.079 (4) Å

b = 8.1963 (7) Å

c = 18.397 (3) Å

β = 131.77 (1)°

V = 2820.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.48 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.822, T max = 0.935

5253 measured reflections

2432 independent reflections

1623 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.115

S = 1.16

2432 reflections

216 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536812015681/nc2273sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015681/nc2273Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015681/nc2273Isup3.cml

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

C14H12ClNO3S	F(000) = 1280
Mr = 309.76	Dx = 1.459 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2528 reflections
a = 25.079 (4) Å	θ = 2.5–27.9°
b = 8.1963 (7) Å	µ = 0.42 mm−1
c = 18.397 (3) Å	T = 293 K
β = 131.77 (1)°	Prism, colourless
V = 2820.4 (7) Å3	0.48 × 0.20 × 0.16 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2432 independent reflections
Radiation source: fine-focus sealed tube	1623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Rotation method data acquisition using ω and phi scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −23→29
Tmin = 0.822, Tmax = 0.935	k = −9→7
5253 measured reflections	l = −21→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0079P)2 + 10.754P] where P = (Fo2 + 2Fc2)/3
2432 reflections	(Δ/σ)max = 0.002
216 parameters	Δρmax = 0.30 e Å−3
15 restraints	Δρmin = −0.31 e Å−3

Experimental. Absorption correction: 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	Occ. (<1)
S1	0.46756 (6)	0.21314 (14)	0.84045 (8)	0.0370 (3)
O1	0.47071 (16)	0.0832 (4)	0.8932 (2)	0.0501 (8)
O2	0.53214 (14)	0.2614 (4)	0.8617 (2)	0.0451 (8)
O3	0.31747 (17)	0.0536 (4)	0.7036 (2)	0.0606 (10)
N1	0.41113 (17)	0.1593 (4)	0.7243 (2)	0.0392 (9)
H1N	0.4221	0.1892	0.6909	0.047*
C1	0.4310 (2)	0.3870 (5)	0.8486 (3)	0.0331 (10)
C2	0.4617 (2)	0.5370 (5)	0.8639 (3)	0.0453 (12)
H2	0.5004	0.5468	0.8677	0.054*
C3	0.4343 (2)	0.6723 (6)	0.8737 (3)	0.0494 (12)
H3	0.4547	0.7741	0.8840	0.059*
C4	0.3767 (2)	0.6586 (6)	0.8682 (3)	0.0408 (11)
C5	0.3469 (2)	0.5060 (6)	0.8526 (3)	0.0475 (12)
H5	0.3079	0.4957	0.8481	0.057*
C6	0.3739 (2)	0.3701 (6)	0.8436 (3)	0.0452 (12)
H6	0.3540	0.2680	0.8343	0.054*
C7	0.3475 (2)	0.0709 (5)	0.6741 (3)	0.0406 (11)
C8	0.3257 (5)	−0.0153 (13)	0.5801 (7)	0.030 (3)	0.537 (3)
C9	0.2525 (4)	−0.0070 (12)	0.4939 (6)	0.031 (2)	0.537 (3)
C10	0.2260 (5)	−0.0831 (12)	0.4066 (6)	0.031 (2)	0.537 (3)
H10	0.1780	−0.0830	0.3496	0.037*	0.537 (3)
C11	0.2799 (5)	−0.1586 (11)	0.4153 (6)	0.037 (2)	0.537 (3)
H11	0.2667	−0.2112	0.3605	0.044*	0.537 (3)
C12	0.3534 (6)	−0.1611 (11)	0.5014 (7)	0.043 (2)	0.537 (3)
H12	0.3859	−0.2151	0.5011	0.052*	0.537 (3)
C13	0.3767 (6)	−0.0868 (14)	0.5831 (8)	0.040 (3)	0.537 (3)
H13	0.4249	−0.0839	0.6389	0.048*	0.537 (3)
Cl1	0.18345 (12)	0.0821 (3)	0.48116 (17)	0.0546 (8)	0.537 (3)
C8'	0.3105 (7)	0.0155 (17)	0.5785 (9)	0.024 (4)*	0.463 (3)
C9'	0.3503 (7)	−0.090 (2)	0.5695 (10)	0.041 (5)*	0.463 (3)
C10'	0.3175 (8)	−0.158 (2)	0.4767 (11)	0.075 (6)*	0.463 (3)
H10'	0.3420	−0.2235	0.4663	0.089*	0.463 (3)
C11'	0.2470 (8)	−0.118 (2)	0.4041 (11)	0.061 (6)*	0.463 (3)
H11'	0.2244	−0.1571	0.3421	0.073*	0.463 (3)
C12'	0.2056 (8)	−0.0234 (18)	0.4137 (11)	0.083 (5)*	0.463 (3)
H12'	0.1573	−0.0046	0.3610	0.099*	0.463 (3)
C13'	0.2385 (8)	0.0399 (19)	0.5032 (11)	0.066 (5)*	0.463 (3)
H13'	0.2124	0.0995	0.5134	0.079*	0.463 (3)
Cl1'	0.43803 (18)	−0.1591 (4)	0.6657 (3)	0.0793 (13)	0.463 (3)
C14	0.3471 (3)	0.8079 (6)	0.8782 (3)	0.0576 (14)
H14A	0.3478	0.8981	0.8457	0.086*
H14B	0.3757	0.8334	0.9460	0.086*
H14C	0.2987	0.7872	0.8494	0.086*

	U11	U22	U33	U12	U13	U23
S1	0.0378 (6)	0.0369 (6)	0.0381 (6)	−0.0007 (6)	0.0260 (5)	−0.0026 (5)
O1	0.068 (2)	0.0397 (19)	0.0475 (19)	0.0079 (17)	0.0404 (19)	0.0108 (15)
O2	0.0334 (17)	0.054 (2)	0.0472 (18)	−0.0044 (15)	0.0267 (15)	−0.0123 (15)
O3	0.055 (2)	0.079 (3)	0.064 (2)	−0.0214 (19)	0.046 (2)	−0.0109 (19)
N1	0.045 (2)	0.041 (2)	0.038 (2)	−0.0101 (18)	0.0304 (19)	−0.0067 (17)
C1	0.036 (2)	0.033 (3)	0.034 (2)	0.001 (2)	0.024 (2)	0.0004 (19)
C2	0.046 (3)	0.041 (3)	0.061 (3)	−0.008 (2)	0.040 (3)	−0.005 (2)
C3	0.058 (3)	0.035 (3)	0.067 (3)	−0.009 (2)	0.046 (3)	−0.006 (2)
C4	0.045 (3)	0.042 (3)	0.034 (2)	0.009 (2)	0.026 (2)	0.002 (2)
C5	0.048 (3)	0.052 (3)	0.062 (3)	−0.004 (3)	0.045 (3)	−0.005 (3)
C6	0.053 (3)	0.037 (3)	0.063 (3)	−0.006 (2)	0.046 (3)	−0.008 (2)
C7	0.036 (3)	0.038 (3)	0.045 (3)	−0.007 (2)	0.026 (2)	−0.002 (2)
C8	0.024 (5)	0.017 (5)	0.056 (6)	0.010 (4)	0.030 (5)	0.005 (4)
C9	0.034 (5)	0.032 (6)	0.035 (5)	0.001 (4)	0.026 (5)	0.001 (4)
C10	0.024 (5)	0.038 (6)	0.041 (5)	0.007 (4)	0.026 (5)	0.000 (4)
C11	0.028 (5)	0.036 (5)	0.036 (6)	0.006 (4)	0.018 (5)	0.002 (4)
C12	0.050 (7)	0.035 (5)	0.063 (7)	0.006 (5)	0.046 (6)	−0.006 (4)
C13	0.041 (7)	0.047 (6)	0.043 (6)	−0.006 (6)	0.032 (6)	−0.011 (5)
Cl1	0.0510 (16)	0.0559 (16)	0.0613 (16)	0.0102 (12)	0.0392 (14)	0.0080 (12)
Cl1'	0.078 (2)	0.065 (2)	0.110 (3)	−0.0042 (18)	0.069 (2)	−0.0242 (19)
C14	0.066 (3)	0.054 (3)	0.055 (3)	0.017 (3)	0.041 (3)	0.005 (3)

S1—O1	1.407 (3)	C9—Cl1	1.745 (9)
S1—O2	1.446 (3)	C10—C11	1.397 (12)
S1—N1	1.654 (3)	C10—H10	0.9300
S1—C1	1.754 (4)	C11—C12	1.420 (12)
O3—C7	1.195 (5)	C11—H11	0.9300
N1—C7	1.400 (5)	C12—C13	1.342 (11)
N1—H1N	0.8600	C12—H12	0.9300
C1—C2	1.377 (5)	C13—H13	0.9300
C1—C6	1.380 (5)	C8'—C13'	1.373 (17)
C2—C3	1.378 (6)	C8'—C9'	1.412 (15)
C2—H2	0.9300	C9'—C10'	1.423 (16)
C3—C4	1.384 (6)	C9'—Cl1'	1.762 (13)
C3—H3	0.9300	C10'—C11'	1.368 (15)
C4—C5	1.385 (6)	C10'—H10'	0.9300
C4—C14	1.506 (6)	C11'—C12'	1.398 (14)
C5—C6	1.369 (6)	C11'—H11'	0.9300
C5—H5	0.9300	C12'—C13'	1.360 (16)
C6—H6	0.9300	C12'—H12'	0.9300
C7—C8'	1.408 (12)	C13'—H13'	0.9300
C7—C8	1.589 (11)	C14—H14A	0.9600
C8—C13	1.374 (14)	C14—H14B	0.9600
C8—C9	1.419 (12)	C14—H14C	0.9600
C9—C10	1.410 (12)
O1—S1—O2	118.86 (19)	C8—C9—Cl1	126.8 (7)
O1—S1—N1	107.20 (18)	C11—C10—C9	112.3 (8)
O2—S1—N1	105.20 (17)	C11—C10—H10	123.8
O1—S1—C1	110.41 (19)	C9—C10—H10	123.8
O2—S1—C1	108.09 (19)	C10—C11—C12	124.9 (7)
N1—S1—C1	106.31 (18)	C10—C11—H11	117.5
C7—N1—S1	127.5 (3)	C12—C11—H11	117.5
C7—N1—H1N	116.2	C13—C12—C11	121.1 (9)
S1—N1—H1N	116.2	C13—C12—H12	119.5
C2—C1—C6	121.2 (4)	C11—C12—H12	119.5
C2—C1—S1	119.3 (3)	C12—C13—C8	116.7 (11)
C6—C1—S1	119.5 (3)	C12—C13—H13	121.6
C1—C2—C3	119.0 (4)	C8—C13—H13	121.6
C1—C2—H2	120.5	C13'—C8'—C7	122.9 (11)
C3—C2—H2	120.5	C13'—C8'—C9'	121.9 (12)
C2—C3—C4	120.8 (4)	C7—C8'—C9'	114.5 (10)
C2—C3—H3	119.6	C8'—C9'—C10'	119.3 (12)
C4—C3—H3	119.6	C8'—C9'—Cl1'	125.9 (10)
C3—C4—C5	118.7 (4)	C10'—C9'—Cl1'	114.7 (12)
C3—C4—C14	120.1 (4)	C11'—C10'—C9'	114.7 (13)
C5—C4—C14	121.1 (4)	C11'—C10'—H10'	122.7
C6—C5—C4	121.2 (4)	C9'—C10'—H10'	122.7
C6—C5—H5	119.4	C10'—C11'—C12'	126.5 (15)
C4—C5—H5	119.4	C10'—C11'—H11'	116.8
C5—C6—C1	119.0 (4)	C12'—C11'—H11'	116.8
C5—C6—H6	120.5	C13'—C12'—C11'	117.5 (15)
C1—C6—H6	120.5	C13'—C12'—H12'	121.3
O3—C7—N1	123.2 (4)	C11'—C12'—H12'	121.3
O3—C7—C8'	115.9 (7)	C12'—C13'—C8'	119.7 (13)
N1—C7—C8'	120.3 (7)	C12'—C13'—H13'	120.1
O3—C7—C8	125.2 (5)	C8'—C13'—H13'	120.1
N1—C7—C8	111.3 (5)	C4—C14—H14A	109.5
C8'—C7—C8	15.5 (7)	C4—C14—H14B	109.5
C13—C8—C9	122.8 (9)	H14A—C14—H14B	109.5
C13—C8—C7	120.6 (8)	C4—C14—H14C	109.5
C9—C8—C7	116.5 (8)	H14A—C14—H14C	109.5
C10—C9—C8	122.0 (8)	H14B—C14—H14C	109.5
C10—C9—Cl1	111.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.02	2.867 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.02	2.867 (4)	169

Symmetry code: (i) .