4-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 mol-ecule is twisted at the S atom with a torsion angle of 69.0 (2)°. The dihedral angle between the sulfonyl benzene ring and the -SO(2)-NH-C-O segment is 77.2 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.5 (1)°. In the structure, mol-ecules are linked into chains via N-H⋯O hydrogen bonds, forming inversion 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. (2009 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Orthorhombic,

a = 13.719 (1) Å

b = 9.6781 (9) Å

c = 21.102 (2) Å

V = 2801.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 299 K

0.34 × 0.24 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.868, T max = 0.943

6658 measured reflections

2840 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.123

S = 1.02

2840 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.38 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/S1600536810019501/ds2033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019501/ds2033Isup2.hkl

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

C14H12ClNO3S	F(000) = 1280
Mr = 309.76	Dx = 1.469 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2077 reflections
a = 13.719 (1) Å	θ = 2.6–27.8°
b = 9.6781 (9) Å	µ = 0.43 mm−1
c = 21.102 (2) Å	T = 299 K
V = 2801.8 (4) Å3	Rod, colourless
Z = 8	0.34 × 0.24 × 0.14 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2840 independent reflections
Radiation source: fine-focus sealed tube	1902 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→17
Tmin = 0.868, Tmax = 0.943	k = −7→12
6658 measured reflections	l = −26→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0556P)2 + 1.3127P] where P = (Fo2 + 2Fc2)/3
2840 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.38 e Å−3

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	0.01547 (17)	0.2340 (2)	0.44377 (11)	0.0399 (6)
C2	−0.0141 (2)	0.1166 (3)	0.41247 (14)	0.0546 (7)
H2	0.0228	0.0362	0.4151	0.066*
C3	−0.0983 (2)	0.1187 (3)	0.37717 (15)	0.0594 (8)
H3	−0.1187	0.0399	0.3557	0.071*
C4	−0.15186 (19)	0.2375 (3)	0.37395 (13)	0.0498 (7)
C5	−0.1248 (2)	0.3538 (3)	0.40560 (15)	0.0647 (9)
H5	−0.1630	0.4331	0.4037	0.078*
C6	−0.0399 (2)	0.3523 (3)	0.44044 (14)	0.0601 (8)
H6	−0.0200	0.4315	0.4618	0.072*
C7	0.23281 (17)	0.3764 (2)	0.40867 (12)	0.0396 (6)
C8	0.31666 (17)	0.3739 (2)	0.36415 (12)	0.0389 (6)
C9	0.31635 (19)	0.4681 (3)	0.31449 (13)	0.0477 (7)
H9	0.2653	0.5307	0.3105	0.057*
C10	0.3915 (2)	0.4689 (3)	0.27110 (13)	0.0543 (7)
H10	0.3895	0.5311	0.2375	0.065*
C11	0.47023 (19)	0.3788 (3)	0.27635 (13)	0.0485 (7)
C12	0.47077 (19)	0.2883 (3)	0.32716 (14)	0.0505 (7)
H12	0.5236	0.2291	0.3325	0.061*
C13	0.39507 (17)	0.2836 (2)	0.37016 (13)	0.0452 (6)
H13	0.3965	0.2200	0.4032	0.054*
C14	0.5521 (2)	0.3835 (4)	0.22922 (14)	0.0688 (9)
H14A	0.6100	0.4170	0.2496	0.083*
H14B	0.5349	0.4441	0.1950	0.083*
H14C	0.5636	0.2923	0.2129	0.083*
N1	0.21363 (15)	0.25385 (19)	0.43927 (10)	0.0426 (5)
H1N	0.2442 (17)	0.1798 (17)	0.4294 (12)	0.051*
O1	0.11997 (14)	0.3386 (2)	0.53406 (9)	0.0630 (6)
O2	0.13812 (14)	0.0896 (2)	0.51002 (10)	0.0652 (6)
O3	0.18237 (12)	0.47861 (16)	0.41670 (9)	0.0508 (5)
Cl1	−0.25653 (6)	0.24046 (10)	0.32788 (4)	0.0778 (3)
S1	0.12257 (5)	0.22796 (7)	0.48971 (3)	0.0467 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0343 (12)	0.0428 (13)	0.0427 (13)	−0.0006 (11)	0.0059 (11)	0.0013 (11)
C2	0.0459 (16)	0.0424 (15)	0.076 (2)	0.0001 (12)	0.0084 (15)	−0.0008 (14)
C3	0.0526 (17)	0.0527 (17)	0.073 (2)	−0.0120 (14)	0.0018 (16)	−0.0128 (15)
C4	0.0354 (13)	0.0656 (19)	0.0484 (15)	−0.0080 (13)	0.0021 (12)	−0.0025 (14)
C5	0.0543 (18)	0.0612 (19)	0.079 (2)	0.0170 (15)	−0.0166 (17)	−0.0161 (16)
C6	0.0596 (19)	0.0487 (16)	0.072 (2)	0.0117 (14)	−0.0163 (16)	−0.0231 (15)
C7	0.0333 (12)	0.0321 (12)	0.0533 (15)	−0.0024 (10)	−0.0082 (11)	−0.0003 (11)
C8	0.0307 (12)	0.0315 (12)	0.0546 (15)	−0.0052 (10)	−0.0063 (12)	0.0027 (11)
C9	0.0404 (14)	0.0418 (14)	0.0610 (17)	0.0024 (11)	−0.0080 (14)	0.0111 (13)
C10	0.0506 (16)	0.0581 (17)	0.0543 (17)	−0.0041 (14)	−0.0065 (14)	0.0172 (14)
C11	0.0400 (14)	0.0534 (16)	0.0521 (16)	−0.0047 (12)	−0.0018 (13)	0.0007 (13)
C12	0.0374 (13)	0.0434 (14)	0.0708 (18)	0.0016 (11)	0.0027 (13)	0.0051 (14)
C13	0.0381 (14)	0.0341 (13)	0.0634 (17)	−0.0007 (11)	−0.0008 (12)	0.0102 (12)
C14	0.0534 (17)	0.092 (2)	0.061 (2)	−0.0003 (17)	0.0042 (16)	0.0058 (17)
N1	0.0375 (11)	0.0293 (10)	0.0609 (14)	0.0022 (9)	0.0068 (10)	0.0059 (10)
O1	0.0613 (13)	0.0790 (14)	0.0488 (11)	0.0100 (11)	−0.0077 (10)	−0.0115 (10)
O2	0.0522 (12)	0.0624 (12)	0.0811 (14)	0.0026 (9)	0.0055 (11)	0.0353 (11)
O3	0.0428 (10)	0.0329 (9)	0.0768 (13)	0.0056 (8)	0.0008 (10)	0.0044 (9)
Cl1	0.0498 (4)	0.1078 (7)	0.0758 (6)	−0.0148 (4)	−0.0150 (4)	0.0022 (5)
S1	0.0408 (4)	0.0505 (4)	0.0489 (4)	0.0031 (3)	0.0019 (3)	0.0095 (3)

C1—C2	1.375 (3)	C9—C10	1.379 (4)
C1—C6	1.376 (3)	C9—H9	0.9300
C1—S1	1.761 (3)	C10—C11	1.393 (4)
C2—C3	1.375 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.384 (4)
C3—C4	1.366 (4)	C11—C14	1.500 (4)
C3—H3	0.9300	C12—C13	1.380 (4)
C4—C5	1.360 (4)	C12—H12	0.9300
C4—Cl1	1.734 (3)	C13—H13	0.9300
C5—C6	1.377 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.219 (3)	N1—S1	1.660 (2)
C7—N1	1.376 (3)	N1—H1N	0.856 (10)
C7—C8	1.485 (3)	O1—S1	1.423 (2)
C8—C9	1.389 (3)	O2—S1	1.4224 (19)
C8—C13	1.392 (3)
C2—C1—C6	120.0 (2)	C9—C10—C11	121.6 (3)
C2—C1—S1	118.9 (2)	C9—C10—H10	119.2
C6—C1—S1	121.1 (2)	C11—C10—H10	119.2
C1—C2—C3	119.7 (3)	C12—C11—C10	117.5 (3)
C1—C2—H2	120.1	C12—C11—C14	121.9 (3)
C3—C2—H2	120.1	C10—C11—C14	120.6 (3)
C4—C3—C2	119.4 (3)	C13—C12—C11	121.8 (2)
C4—C3—H3	120.3	C13—C12—H12	119.1
C2—C3—H3	120.3	C11—C12—H12	119.1
C5—C4—C3	121.7 (3)	C12—C13—C8	120.1 (2)
C5—C4—Cl1	119.2 (2)	C12—C13—H13	120.0
C3—C4—Cl1	119.1 (2)	C8—C13—H13	120.0
C4—C5—C6	119.0 (3)	C11—C14—H14A	109.5
C4—C5—H5	120.5	C11—C14—H14B	109.5
C6—C5—H5	120.5	H14A—C14—H14B	109.5
C1—C6—C5	120.2 (3)	C11—C14—H14C	109.5
C1—C6—H6	119.9	H14A—C14—H14C	109.5
C5—C6—H6	119.9	H14B—C14—H14C	109.5
O3—C7—N1	121.7 (2)	C7—N1—S1	125.09 (17)
O3—C7—C8	122.7 (2)	C7—N1—H1N	121.0 (18)
N1—C7—C8	115.5 (2)	S1—N1—H1N	113.4 (18)
C9—C8—C13	118.9 (2)	O2—S1—O1	120.95 (13)
C9—C8—C7	117.7 (2)	O2—S1—N1	102.86 (11)
C13—C8—C7	123.5 (2)	O1—S1—N1	109.09 (12)
C10—C9—C8	120.2 (2)	O2—S1—C1	108.79 (12)
C10—C9—H9	119.9	O1—S1—C1	108.44 (12)
C8—C9—H9	119.9	N1—S1—C1	105.66 (11)
C6—C1—C2—C3	0.9 (4)	C9—C10—C11—C14	−178.8 (3)
S1—C1—C2—C3	179.0 (2)	C10—C11—C12—C13	2.0 (4)
C1—C2—C3—C4	−0.3 (4)	C14—C11—C12—C13	−179.5 (3)
C2—C3—C4—C5	−1.0 (5)	C11—C12—C13—C8	−1.8 (4)
C2—C3—C4—Cl1	178.5 (2)	C9—C8—C13—C12	−0.1 (4)
C3—C4—C5—C6	1.6 (5)	C7—C8—C13—C12	−179.4 (2)
Cl1—C4—C5—C6	−177.9 (2)	O3—C7—N1—S1	0.0 (4)
C2—C1—C6—C5	−0.2 (4)	C8—C7—N1—S1	−178.24 (17)
S1—C1—C6—C5	−178.3 (2)	C7—N1—S1—O2	−177.0 (2)
C4—C5—C6—C1	−1.0 (5)	C7—N1—S1—O1	−47.4 (2)
O3—C7—C8—C9	−24.1 (4)	C7—N1—S1—C1	69.0 (2)
N1—C7—C8—C9	154.1 (2)	C2—C1—S1—O2	−26.1 (2)
O3—C7—C8—C13	155.3 (3)	C6—C1—S1—O2	152.0 (2)
N1—C7—C8—C13	−26.5 (3)	C2—C1—S1—O1	−159.4 (2)
C13—C8—C9—C10	1.7 (4)	C6—C1—S1—O1	18.6 (3)
C7—C8—C9—C10	−178.9 (2)	C2—C1—S1—N1	83.7 (2)
C8—C9—C10—C11	−1.5 (4)	C6—C1—S1—N1	−98.2 (2)
C9—C10—C11—C12	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86 (1)	2.21 (1)	3.059 (3)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86 (1)	2.21 (1)	3.059 (3)	172 (2)

Symmetry code: (i) .