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

In the title compound, C(14)H(12)ClNO(3)S, the N-H bond is anti-periplanar to the C=O bond. The dihedral angle between the two aromatic rings is 78.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of N-aryl sulfonamides and for related structures, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Monoclinic,

a = 6.6086 (5) Å

b = 10.9621 (9) Å

c = 20.080 (2) Å

β = 95.586 (8)°

V = 1447.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 299 K

0.34 × 0.32 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.872, T max = 0.893

5395 measured reflections

2917 independent reflections

2592 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.07

2917 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S1600536810015990/bt5259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015990/bt5259Isup2.hkl

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

C14H12ClNO3S	F(000) = 640
Mr = 309.76	Dx = 1.421 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3866 reflections
a = 6.6086 (5) Å	θ = 2.7–27.8°
b = 10.9621 (9) Å	µ = 0.41 mm−1
c = 20.080 (2) Å	T = 299 K
β = 95.586 (8)°	Prism, colourless
V = 1447.8 (2) Å3	0.34 × 0.32 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2917 independent reflections
Radiation source: fine-focus sealed tube	2592 reflections with I > 2σ(I)
graphite	Rint = 0.017
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 = −7→8
Tmin = 0.872, Tmax = 0.893	k = −13→7
5395 measured reflections	l = −25→25

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.7805P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2917 reflections	Δρmax = 0.31 e Å−3
186 parameters	Δρmin = −0.32 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: 0.146 (5)

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	0.2188 (3)	0.22154 (17)	0.45434 (9)	0.0389 (4)
C2	0.3529 (3)	0.2921 (2)	0.42162 (11)	0.0504 (5)
C3	0.5045 (4)	0.2357 (3)	0.38928 (13)	0.0717 (8)
H3	0.5940	0.2821	0.3667	0.086*
C4	0.5208 (4)	0.1097 (3)	0.39104 (14)	0.0771 (9)
H4	0.6237	0.0719	0.3702	0.092*
C5	0.3890 (4)	0.0403 (3)	0.42274 (13)	0.0658 (7)
H5	0.4005	−0.0443	0.4228	0.079*
C6	0.2392 (4)	0.0956 (2)	0.45452 (10)	0.0502 (5)
H6	0.1500	0.0480	0.4765	0.060*
C7	0.2598 (3)	0.30250 (17)	0.61222 (9)	0.0392 (4)
C8	0.3281 (3)	0.38164 (17)	0.67032 (9)	0.0389 (4)
C9	0.5185 (3)	0.3631 (2)	0.70605 (11)	0.0492 (5)
C10	0.5679 (4)	0.4362 (3)	0.76164 (13)	0.0661 (7)
H10	0.6937	0.4257	0.7860	0.079*
C11	0.4385 (4)	0.5231 (3)	0.78199 (13)	0.0680 (7)
H11	0.4759	0.5693	0.8201	0.082*
C12	0.2534 (4)	0.5422 (2)	0.74615 (12)	0.0608 (6)
H12	0.1660	0.6020	0.7594	0.073*
C13	0.1982 (3)	0.4717 (2)	0.69029 (10)	0.0472 (5)
H13	0.0731	0.4845	0.6658	0.057*
C14	0.6730 (4)	0.2723 (3)	0.68618 (15)	0.0696 (7)
H14A	0.6814	0.2770	0.6388	0.083*
H14B	0.6325	0.1915	0.6977	0.083*
H14C	0.8034	0.2905	0.7094	0.083*
N1	0.1386 (3)	0.36014 (14)	0.56089 (8)	0.0412 (4)
H1N	0.135 (3)	0.4361 (15)	0.5574 (11)	0.049*
O1	−0.0894 (2)	0.18713 (14)	0.52207 (8)	0.0559 (4)
O2	−0.0831 (2)	0.37563 (12)	0.45683 (8)	0.0497 (4)
O3	0.3005 (3)	0.19555 (13)	0.60869 (7)	0.0554 (4)
Cl1	0.34073 (12)	0.45035 (6)	0.42249 (4)	0.0807 (3)
S1	0.02324 (7)	0.28443 (4)	0.49721 (2)	0.03857 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (10)	0.0355 (10)	0.0351 (9)	0.0007 (8)	−0.0027 (7)	−0.0024 (7)
C2	0.0472 (11)	0.0577 (13)	0.0447 (11)	−0.0085 (10)	−0.0030 (9)	0.0012 (9)
C3	0.0462 (12)	0.117 (3)	0.0523 (13)	−0.0120 (14)	0.0068 (10)	−0.0090 (15)
C4	0.0600 (15)	0.108 (2)	0.0607 (15)	0.0241 (16)	−0.0054 (12)	−0.0369 (16)
C5	0.0772 (17)	0.0629 (16)	0.0551 (14)	0.0211 (13)	−0.0052 (12)	−0.0178 (12)
C6	0.0670 (13)	0.0384 (11)	0.0440 (11)	0.0063 (10)	0.0001 (9)	−0.0051 (9)
C7	0.0477 (10)	0.0337 (9)	0.0366 (9)	0.0017 (8)	0.0067 (8)	0.0037 (7)
C8	0.0473 (10)	0.0349 (9)	0.0351 (9)	−0.0035 (8)	0.0076 (8)	0.0031 (7)
C9	0.0507 (11)	0.0501 (12)	0.0465 (11)	−0.0030 (9)	0.0038 (9)	0.0045 (9)
C10	0.0616 (14)	0.0768 (18)	0.0574 (14)	−0.0082 (13)	−0.0074 (11)	−0.0048 (13)
C11	0.0824 (18)	0.0715 (17)	0.0497 (13)	−0.0146 (14)	0.0038 (12)	−0.0161 (12)
C12	0.0743 (15)	0.0569 (14)	0.0534 (13)	0.0010 (12)	0.0185 (11)	−0.0140 (11)
C13	0.0527 (11)	0.0465 (11)	0.0432 (10)	0.0024 (9)	0.0085 (9)	−0.0018 (9)
C14	0.0565 (14)	0.0680 (17)	0.0833 (18)	0.0118 (12)	0.0019 (13)	0.0033 (14)
N1	0.0570 (10)	0.0242 (7)	0.0411 (8)	0.0016 (7)	−0.0015 (7)	−0.0002 (6)
O1	0.0591 (9)	0.0400 (8)	0.0701 (10)	−0.0135 (7)	0.0146 (8)	−0.0011 (7)
O2	0.0509 (8)	0.0349 (7)	0.0597 (9)	0.0040 (6)	−0.0124 (7)	−0.0026 (6)
O3	0.0846 (11)	0.0320 (7)	0.0483 (8)	0.0118 (7)	−0.0006 (7)	0.0017 (6)
Cl1	0.0810 (5)	0.0573 (4)	0.1049 (6)	−0.0258 (3)	0.0148 (4)	0.0216 (4)
S1	0.0428 (3)	0.0266 (3)	0.0456 (3)	−0.00243 (18)	0.00085 (19)	−0.00064 (18)

C1—C6	1.387 (3)	C9—C10	1.387 (3)
C1—C2	1.389 (3)	C9—C14	1.507 (3)
C1—S1	1.761 (2)	C10—C11	1.369 (4)
C2—C3	1.391 (4)	C10—H10	0.9300
C2—Cl1	1.737 (3)	C11—C12	1.373 (4)
C3—C4	1.386 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.382 (3)
C4—C5	1.361 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.370 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.206 (2)	N1—S1	1.6478 (17)
C7—N1	1.394 (2)	N1—H1N	0.836 (16)
C7—C8	1.488 (3)	O1—S1	1.4188 (15)
C8—C13	1.393 (3)	O2—S1	1.4283 (14)
C8—C9	1.401 (3)
C6—C1—C2	119.3 (2)	C11—C10—C9	122.5 (2)
C6—C1—S1	117.65 (17)	C11—C10—H10	118.7
C2—C1—S1	123.06 (16)	C9—C10—H10	118.7
C1—C2—C3	119.7 (2)	C10—C11—C12	120.0 (2)
C1—C2—Cl1	121.28 (18)	C10—C11—H11	120.0
C3—C2—Cl1	119.0 (2)	C12—C11—H11	120.0
C4—C3—C2	119.2 (3)	C11—C12—C13	119.5 (2)
C4—C3—H3	120.4	C11—C12—H12	120.3
C2—C3—H3	120.4	C13—C12—H12	120.3
C5—C4—C3	121.2 (2)	C12—C13—C8	120.6 (2)
C5—C4—H4	119.4	C12—C13—H13	119.7
C3—C4—H4	119.4	C8—C13—H13	119.7
C4—C5—C6	119.7 (3)	C9—C14—H14A	109.5
C4—C5—H5	120.2	C9—C14—H14B	109.5
C6—C5—H5	120.2	H14A—C14—H14B	109.5
C5—C6—C1	120.9 (2)	C9—C14—H14C	109.5
C5—C6—H6	119.5	H14A—C14—H14C	109.5
C1—C6—H6	119.5	H14B—C14—H14C	109.5
O3—C7—N1	120.83 (18)	C7—N1—S1	122.33 (13)
O3—C7—C8	124.07 (18)	C7—N1—H1N	121.6 (16)
N1—C7—C8	115.09 (16)	S1—N1—H1N	115.4 (16)
C13—C8—C9	120.23 (19)	O1—S1—O2	118.67 (10)
C13—C8—C7	119.36 (18)	O1—S1—N1	108.94 (9)
C9—C8—C7	120.38 (18)	O2—S1—N1	104.66 (8)
C10—C9—C8	117.2 (2)	O1—S1—C1	108.22 (9)
C10—C9—C14	118.8 (2)	O2—S1—C1	109.90 (9)
C8—C9—C14	123.9 (2)	N1—S1—C1	105.69 (9)
C6—C1—C2—C3	0.4 (3)	C8—C9—C10—C11	0.2 (4)
S1—C1—C2—C3	179.48 (17)	C14—C9—C10—C11	178.2 (3)
C6—C1—C2—Cl1	−177.48 (16)	C9—C10—C11—C12	−1.3 (4)
S1—C1—C2—Cl1	1.6 (2)	C10—C11—C12—C13	1.0 (4)
C1—C2—C3—C4	−0.8 (3)	C11—C12—C13—C8	0.2 (4)
Cl1—C2—C3—C4	177.1 (2)	C9—C8—C13—C12	−1.2 (3)
C2—C3—C4—C5	1.2 (4)	C7—C8—C13—C12	176.6 (2)
C3—C4—C5—C6	−1.1 (4)	O3—C7—N1—S1	7.1 (3)
C4—C5—C6—C1	0.6 (4)	C8—C7—N1—S1	−171.69 (14)
C2—C1—C6—C5	−0.2 (3)	C7—N1—S1—O1	52.08 (18)
S1—C1—C6—C5	−179.40 (17)	C7—N1—S1—O2	179.96 (16)
O3—C7—C8—C13	−143.2 (2)	C7—N1—S1—C1	−64.00 (18)
N1—C7—C8—C13	35.5 (3)	C6—C1—S1—O1	−3.36 (19)
O3—C7—C8—C9	34.6 (3)	C2—C1—S1—O1	177.51 (16)
N1—C7—C8—C9	−146.66 (19)	C6—C1—S1—O2	−134.38 (16)
C13—C8—C9—C10	1.0 (3)	C2—C1—S1—O2	46.49 (18)
C7—C8—C9—C10	−176.8 (2)	C6—C1—S1—N1	113.21 (16)
C13—C8—C9—C14	−176.9 (2)	C2—C1—S1—N1	−65.91 (18)
C7—C8—C9—C14	5.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.11 (2)	2.937 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.11 (2)	2.937 (2)	172 (2)

Symmetry code: (i) .