2-Chloro-N-(4-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 dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 89.4 (1)° and that between the sulfonyl and benzoyl benzene rings is 89.1 (2)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

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

Monoclinic,

a = 8.0554 (8) Å

b = 23.209 (2) Å

c = 8.1199 (9) Å

β = 103.52 (1)°

V = 1476.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 299 K

0.40 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.855, T max = 0.906

6106 measured reflections

3012 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.153

S = 1.07

3012 reflections

184 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.54 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/S1600536810018908/bq2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018908/bq2212Isup2.hkl

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

C14H12ClNO3S	F(000) = 640
Mr = 309.76	Dx = 1.394 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2713 reflections
a = 8.0554 (8) Å	θ = 2.6–27.7°
b = 23.209 (2) Å	µ = 0.41 mm−1
c = 8.1199 (9) Å	T = 299 K
β = 103.52 (1)°	Prism, colourless
V = 1476.0 (3) Å3	0.40 × 0.30 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3012 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→7
Tmin = 0.855, Tmax = 0.906	k = −29→20
6106 measured reflections	l = −7→10

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0583P)2 + 1.5332P] where P = (Fo2 + 2Fc2)/3
3012 reflections	(Δ/σ)max = 0.009
184 parameters	Δρmax = 0.43 e Å−3
19 restraints	Δρmin = −0.54 e Å−3

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

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
C1	0.8834 (4)	0.06157 (12)	0.7360 (4)	0.0399 (6)
C2	0.8115 (5)	0.05804 (15)	0.8744 (5)	0.0609 (9)
C3	0.9088 (9)	0.0714 (2)	1.0333 (6)	0.1017 (18)
H3	0.8610	0.0693	1.1268	0.122*
C4	1.0737 (10)	0.0875 (3)	1.0534 (7)	0.112 (2)
H4	1.1389	0.0957	1.1614	0.135*
C5	1.1463 (6)	0.0921 (2)	0.9173 (7)	0.0901 (15)
H5	1.2589	0.1042	0.9325	0.108*
C6	1.0509 (4)	0.07867 (14)	0.7569 (5)	0.0564 (8)
H6	1.0995	0.0812	0.6639	0.068*
C7	0.6201 (4)	0.14562 (15)	0.4825 (5)	0.0553 (8)
C8	0.4601 (4)	0.17935 (14)	0.4640 (5)	0.0525 (8)
C9	0.4691 (6)	0.23742 (19)	0.4380 (8)	0.1039 (18)
H9	0.5712	0.2538	0.4266	0.125*
C10	0.3274 (6)	0.27170 (19)	0.4289 (9)	0.113 (2)
H10	0.3359	0.3110	0.4108	0.136*
C11	0.1739 (5)	0.24948 (16)	0.4456 (6)	0.0738 (12)
C12	0.1647 (4)	0.19155 (15)	0.4642 (6)	0.0667 (10)
H12	0.0615	0.1750	0.4714	0.080*
C13	0.3054 (4)	0.15666 (14)	0.4729 (5)	0.0581 (9)
H13	0.2950	0.1171	0.4849	0.070*
C14	0.0207 (6)	0.2878 (2)	0.4412 (8)	0.1062 (18)
H14A	−0.0105	0.3071	0.3338	0.127*
H14B	0.0489	0.3159	0.5302	0.127*
H14C	−0.0733	0.2648	0.4570	0.127*
N1	0.6050 (3)	0.08618 (12)	0.4850 (4)	0.0524 (7)
H1N	0.511 (3)	0.0699 (15)	0.482 (5)	0.063*
O1	0.8805 (3)	0.05469 (13)	0.4188 (3)	0.0701 (7)
O2	0.7012 (3)	−0.01317 (10)	0.5312 (4)	0.0727 (8)
O3	0.7585 (3)	0.16727 (12)	0.4989 (5)	0.0902 (10)
Cl1	0.60112 (17)	0.03731 (6)	0.85557 (19)	0.1056 (5)
S1	0.77166 (9)	0.04311 (3)	0.52941 (10)	0.0470 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0441 (15)	0.0354 (14)	0.0400 (15)	0.0042 (12)	0.0098 (12)	0.0020 (12)
C2	0.083 (2)	0.0542 (19)	0.053 (2)	0.0150 (18)	0.0314 (18)	0.0112 (16)
C3	0.165 (6)	0.097 (4)	0.047 (2)	0.046 (4)	0.034 (3)	0.008 (2)
C4	0.140 (5)	0.105 (4)	0.067 (3)	0.035 (4)	−0.027 (3)	−0.023 (3)
C5	0.072 (3)	0.077 (3)	0.098 (4)	−0.001 (2)	−0.027 (3)	−0.013 (3)
C6	0.0454 (17)	0.0522 (19)	0.067 (2)	−0.0015 (14)	0.0028 (15)	0.0024 (16)
C7	0.0408 (17)	0.0527 (19)	0.072 (2)	0.0017 (14)	0.0127 (15)	0.0123 (16)
C8	0.0416 (16)	0.0453 (17)	0.070 (2)	0.0008 (13)	0.0113 (15)	0.0130 (15)
C9	0.062 (2)	0.058 (2)	0.194 (5)	0.0004 (19)	0.035 (3)	0.035 (3)
C10	0.079 (3)	0.049 (2)	0.214 (6)	0.010 (2)	0.040 (3)	0.038 (3)
C11	0.056 (2)	0.048 (2)	0.117 (4)	0.0122 (16)	0.019 (2)	0.020 (2)
C12	0.0449 (17)	0.050 (2)	0.107 (3)	0.0012 (15)	0.0212 (19)	0.007 (2)
C13	0.0466 (17)	0.0397 (17)	0.089 (3)	−0.0005 (14)	0.0184 (17)	0.0054 (16)
C14	0.079 (3)	0.070 (3)	0.174 (6)	0.030 (2)	0.037 (3)	0.027 (3)
N1	0.0356 (13)	0.0464 (15)	0.0708 (18)	0.0023 (11)	0.0038 (12)	−0.0026 (13)
O1	0.0647 (15)	0.106 (2)	0.0433 (13)	0.0244 (14)	0.0207 (11)	0.0014 (13)
O2	0.0460 (13)	0.0452 (14)	0.118 (2)	0.0032 (10)	0.0014 (13)	−0.0245 (14)
O3	0.0441 (14)	0.0663 (17)	0.163 (3)	−0.0014 (12)	0.0291 (16)	0.0272 (18)
Cl1	0.1019 (9)	0.1066 (9)	0.1379 (12)	0.0130 (7)	0.0877 (9)	0.0378 (8)
S1	0.0388 (4)	0.0499 (4)	0.0500 (4)	0.0057 (3)	0.0059 (3)	−0.0087 (3)

C1—C6	1.378 (4)	C9—C10	1.379 (6)
C1—C2	1.381 (4)	C9—H9	0.9300
C1—S1	1.761 (3)	C10—C11	1.376 (6)
C2—C3	1.379 (7)	C10—H10	0.9300
C2—Cl1	1.734 (4)	C11—C12	1.357 (5)
C3—C4	1.353 (8)	C11—C14	1.515 (5)
C3—H3	0.9300	C12—C13	1.382 (5)
C4—C5	1.370 (8)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.384 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.201 (4)	N1—S1	1.645 (3)
C7—N1	1.385 (4)	N1—H1N	0.840 (19)
C7—C8	1.485 (4)	O1—S1	1.420 (3)
C8—C9	1.369 (5)	O2—S1	1.426 (3)
C8—C13	1.370 (4)
C6—C1—C2	120.1 (3)	C11—C10—C9	122.0 (4)
C6—C1—S1	117.1 (2)	C11—C10—H10	119.0
C2—C1—S1	122.8 (3)	C9—C10—H10	119.0
C3—C2—C1	119.5 (4)	C12—C11—C10	117.1 (4)
C3—C2—Cl1	118.3 (4)	C12—C11—C14	121.3 (4)
C1—C2—Cl1	122.1 (3)	C10—C11—C14	121.6 (4)
C4—C3—C2	120.2 (5)	C11—C12—C13	121.4 (3)
C4—C3—H3	119.9	C11—C12—H12	119.3
C2—C3—H3	119.9	C13—C12—H12	119.3
C3—C4—C5	121.1 (5)	C8—C13—C12	121.2 (3)
C3—C4—H4	119.5	C8—C13—H13	119.4
C5—C4—H4	119.5	C12—C13—H13	119.4
C4—C5—C6	119.6 (5)	C11—C14—H14A	109.5
C4—C5—H5	120.2	C11—C14—H14B	109.5
C6—C5—H5	120.2	H14A—C14—H14B	109.5
C1—C6—C5	119.5 (4)	C11—C14—H14C	109.5
C1—C6—H6	120.2	H14A—C14—H14C	109.5
C5—C6—H6	120.2	H14B—C14—H14C	109.5
O3—C7—N1	119.8 (3)	C7—N1—S1	122.6 (2)
O3—C7—C8	123.5 (3)	C7—N1—H1N	122 (3)
N1—C7—C8	116.7 (3)	S1—N1—H1N	115 (3)
C9—C8—C13	117.9 (3)	O1—S1—O2	119.06 (17)
C9—C8—C7	117.3 (3)	O1—S1—N1	109.85 (16)
C13—C8—C7	124.8 (3)	O2—S1—N1	104.63 (14)
C8—C9—C10	120.2 (4)	O1—S1—C1	107.63 (15)
C8—C9—H9	119.9	O2—S1—C1	109.23 (16)
C10—C9—H9	119.9	N1—S1—C1	105.67 (14)
C6—C1—C2—C3	−0.4 (5)	C9—C10—C11—C12	−2.8 (9)
S1—C1—C2—C3	177.8 (3)	C9—C10—C11—C14	177.9 (6)
C6—C1—C2—Cl1	179.5 (3)	C10—C11—C12—C13	2.5 (7)
S1—C1—C2—Cl1	−2.3 (4)	C14—C11—C12—C13	−178.2 (5)
C1—C2—C3—C4	−0.3 (7)	C9—C8—C13—C12	−3.1 (6)
Cl1—C2—C3—C4	179.8 (4)	C7—C8—C13—C12	176.1 (4)
C2—C3—C4—C5	1.3 (8)	C11—C12—C13—C8	0.4 (7)
C3—C4—C5—C6	−1.6 (8)	O3—C7—N1—S1	6.5 (5)
C2—C1—C6—C5	0.1 (5)	C8—C7—N1—S1	−171.8 (3)
S1—C1—C6—C5	−178.2 (3)	C7—N1—S1—O1	−55.4 (3)
C4—C5—C6—C1	0.9 (6)	C7—N1—S1—O2	175.7 (3)
O3—C7—C8—C9	10.5 (6)	C7—N1—S1—C1	60.4 (3)
N1—C7—C8—C9	−171.3 (4)	C6—C1—S1—O1	−4.7 (3)
O3—C7—C8—C13	−168.8 (4)	C2—C1—S1—O1	177.0 (3)
N1—C7—C8—C13	9.5 (5)	C6—C1—S1—O2	125.9 (2)
C13—C8—C9—C10	2.8 (8)	C2—C1—S1—O2	−52.4 (3)
C7—C8—C9—C10	−176.5 (5)	C6—C1—S1—N1	−122.0 (2)
C8—C9—C10—C11	0.2 (10)	C2—C1—S1—N1	59.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.14 (2)	2.970 (4)	169 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.14 (2)	2.970 (4)	169 (4)

Symmetry code: (i) .