2-Chloro-N-(3-methyl-benzo-yl)benzene-sulfonamide.

In the title compound, C(14)H(12)ClNO(3)S, the N-H bond is in an anti-periplanar conformation to the C=O bond. The dihedral angle between the two aromatic rings is 74.7 (1)°. The crystal structure features inversion-related dimers linked by N-H⋯O 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 ▶, 2010 ▶); Suchetan et al. (2010 ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Orthorhombic,

a = 12.4487 (8) Å

b = 13.4619 (8) Å

c = 17.455 (1) Å

V = 2925.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 299 K

0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.887, T max = 0.923

7216 measured reflections

2955 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.04

2955 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.28 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/S1600536810016235/bt5261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016235/bt5261Isup2.hkl

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

C14H12ClNO3S	F(000) = 1280
Mr = 309.76	Dx = 1.407 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5313 reflections
a = 12.4487 (8) Å	θ = 2.8–27.7°
b = 13.4619 (8) Å	µ = 0.41 mm−1
c = 17.455 (1) Å	T = 299 K
V = 2925.2 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.30 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2955 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→11
Tmin = 0.887, Tmax = 0.923	k = −16→9
7216 measured reflections	l = −12→21

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0429P)2 + 1.518P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2955 reflections	Δρmax = 0.20 e Å−3
186 parameters	Δρmin = −0.28 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: 0.0265 (11)

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	−0.00620 (14)	0.25666 (13)	0.42487 (10)	0.0366 (4)
C2	−0.09360 (15)	0.24307 (16)	0.47300 (11)	0.0452 (5)
C3	−0.1408 (2)	0.15010 (19)	0.47939 (15)	0.0634 (6)
H3	−0.1992	0.1408	0.5118	0.076*
C4	−0.1008 (2)	0.07177 (18)	0.43768 (16)	0.0688 (7)
H4	−0.1323	0.0095	0.4423	0.083*
C5	−0.0152 (2)	0.08419 (16)	0.38944 (15)	0.0627 (6)
H5	0.0109	0.0307	0.3614	0.075*
C6	0.03249 (18)	0.17676 (14)	0.38256 (12)	0.0482 (5)
H6	0.0904	0.1855	0.3496	0.058*
C7	−0.06413 (15)	0.45303 (13)	0.31212 (10)	0.0381 (4)
C8	−0.13360 (15)	0.53961 (13)	0.29432 (10)	0.0373 (4)
C9	−0.11657 (16)	0.63233 (13)	0.32775 (11)	0.0404 (4)
H9	−0.0593	0.6410	0.3613	0.049*
C10	−0.18376 (18)	0.71203 (15)	0.31173 (11)	0.0476 (5)
C11	−0.26884 (18)	0.69666 (18)	0.26178 (13)	0.0581 (6)
H11	−0.3156	0.7487	0.2510	0.070*
C12	−0.28515 (18)	0.60527 (19)	0.22792 (13)	0.0598 (6)
H12	−0.3426	0.5966	0.1946	0.072*
C13	−0.21746 (16)	0.52658 (15)	0.24283 (11)	0.0484 (5)
H13	−0.2278	0.4657	0.2188	0.058*
C14	−0.1632 (2)	0.81144 (17)	0.34798 (15)	0.0693 (7)
H14A	−0.1193	0.8509	0.3145	0.083*
H14B	−0.1267	0.8023	0.3959	0.083*
H14C	−0.2303	0.8447	0.3567	0.083*
N1	−0.01969 (13)	0.45407 (11)	0.38535 (9)	0.0409 (4)
H1N	−0.0421 (17)	0.4933 (14)	0.4174 (11)	0.049*
O1	0.14949 (11)	0.35731 (10)	0.36476 (9)	0.0497 (4)
O2	0.08974 (11)	0.40436 (10)	0.49378 (8)	0.0465 (4)
O3	−0.04744 (13)	0.38456 (10)	0.26879 (8)	0.0528 (4)
Cl1	−0.14827 (5)	0.34034 (5)	0.52560 (4)	0.0706 (2)
S1	0.06458 (4)	0.37028 (3)	0.41809 (3)	0.03622 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0387 (9)	0.0376 (9)	0.0335 (9)	0.0023 (8)	0.0006 (7)	0.0023 (7)
C2	0.0403 (10)	0.0532 (11)	0.0422 (10)	−0.0003 (9)	0.0050 (8)	−0.0039 (9)
C3	0.0539 (13)	0.0707 (15)	0.0656 (15)	−0.0153 (12)	0.0158 (12)	0.0052 (12)
C4	0.0806 (17)	0.0468 (12)	0.0789 (17)	−0.0165 (12)	0.0058 (14)	0.0043 (12)
C5	0.0829 (17)	0.0386 (11)	0.0665 (15)	0.0010 (11)	0.0102 (13)	−0.0030 (10)
C6	0.0581 (12)	0.0400 (10)	0.0464 (11)	0.0047 (9)	0.0100 (10)	0.0002 (9)
C7	0.0421 (10)	0.0362 (9)	0.0362 (9)	−0.0064 (8)	−0.0011 (8)	0.0008 (7)
C8	0.0403 (10)	0.0395 (9)	0.0321 (9)	−0.0028 (8)	−0.0009 (7)	0.0073 (7)
C9	0.0469 (10)	0.0395 (9)	0.0350 (9)	−0.0003 (8)	0.0001 (8)	0.0052 (7)
C10	0.0554 (12)	0.0446 (10)	0.0428 (10)	0.0075 (9)	0.0127 (9)	0.0098 (9)
C11	0.0504 (13)	0.0652 (13)	0.0587 (13)	0.0154 (11)	0.0049 (10)	0.0234 (11)
C12	0.0463 (12)	0.0789 (16)	0.0540 (13)	−0.0044 (11)	−0.0136 (10)	0.0220 (12)
C13	0.0500 (11)	0.0536 (11)	0.0417 (10)	−0.0112 (9)	−0.0079 (9)	0.0090 (9)
C14	0.0911 (18)	0.0452 (12)	0.0716 (16)	0.0147 (12)	0.0123 (14)	0.0024 (11)
N1	0.0514 (9)	0.0365 (8)	0.0349 (8)	0.0099 (7)	−0.0053 (7)	−0.0028 (6)
O1	0.0420 (7)	0.0497 (8)	0.0576 (9)	−0.0001 (6)	0.0114 (7)	0.0031 (7)
O2	0.0493 (8)	0.0466 (7)	0.0438 (8)	0.0065 (6)	−0.0130 (6)	−0.0061 (6)
O3	0.0656 (10)	0.0463 (8)	0.0464 (8)	0.0020 (7)	−0.0051 (7)	−0.0112 (6)
Cl1	0.0563 (4)	0.0847 (4)	0.0708 (4)	0.0028 (3)	0.0242 (3)	−0.0256 (3)
S1	0.0360 (2)	0.0358 (2)	0.0368 (3)	0.00304 (18)	−0.00100 (18)	−0.00045 (18)

C1—C2	1.387 (3)	C9—C10	1.389 (3)
C1—C6	1.391 (3)	C9—H9	0.9300
C1—S1	1.7691 (18)	C10—C11	1.387 (3)
C2—C3	1.387 (3)	C10—C14	1.502 (3)
C2—Cl1	1.738 (2)	C11—C12	1.380 (3)
C3—C4	1.375 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.378 (3)
C4—C5	1.368 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.385 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.210 (2)	N1—S1	1.6430 (16)
C7—N1	1.393 (2)	N1—H1N	0.819 (15)
C7—C8	1.484 (3)	O1—S1	1.4192 (14)
C8—C13	1.389 (3)	O2—S1	1.4333 (14)
C8—C9	1.394 (3)
C2—C1—C6	119.43 (18)	C11—C10—C9	118.1 (2)
C2—C1—S1	123.05 (14)	C11—C10—C14	121.9 (2)
C6—C1—S1	117.43 (14)	C9—C10—C14	120.0 (2)
C1—C2—C3	119.99 (19)	C12—C11—C10	121.0 (2)
C1—C2—Cl1	121.86 (16)	C12—C11—H11	119.5
C3—C2—Cl1	118.14 (16)	C10—C11—H11	119.5
C4—C3—C2	119.8 (2)	C13—C12—C11	121.0 (2)
C4—C3—H3	120.1	C13—C12—H12	119.5
C2—C3—H3	120.1	C11—C12—H12	119.5
C5—C4—C3	120.9 (2)	C12—C13—C8	119.0 (2)
C5—C4—H4	119.5	C12—C13—H13	120.5
C3—C4—H4	119.5	C8—C13—H13	120.5
C4—C5—C6	119.8 (2)	C10—C14—H14A	109.5
C4—C5—H5	120.1	C10—C14—H14B	109.5
C6—C5—H5	120.1	H14A—C14—H14B	109.5
C5—C6—C1	120.1 (2)	C10—C14—H14C	109.5
C5—C6—H6	120.0	H14A—C14—H14C	109.5
C1—C6—H6	120.0	H14B—C14—H14C	109.5
O3—C7—N1	120.86 (17)	C7—N1—S1	124.46 (13)
O3—C7—C8	124.56 (17)	C7—N1—H1N	119.9 (15)
N1—C7—C8	114.55 (16)	S1—N1—H1N	115.0 (15)
C13—C8—C9	119.89 (18)	O1—S1—O2	118.76 (9)
C13—C8—C7	118.31 (17)	O1—S1—N1	109.39 (9)
C9—C8—C7	121.80 (16)	O2—S1—N1	103.91 (8)
C10—C9—C8	121.05 (18)	O1—S1—C1	107.97 (8)
C10—C9—H9	119.5	O2—S1—C1	108.90 (8)
C8—C9—H9	119.5	N1—S1—C1	107.39 (8)
C6—C1—C2—C3	0.8 (3)	C8—C9—C10—C14	−179.49 (19)
S1—C1—C2—C3	−175.56 (17)	C9—C10—C11—C12	−1.1 (3)
C6—C1—C2—Cl1	−178.29 (16)	C14—C10—C11—C12	178.7 (2)
S1—C1—C2—Cl1	5.3 (2)	C10—C11—C12—C13	0.1 (3)
C1—C2—C3—C4	−0.2 (4)	C11—C12—C13—C8	1.7 (3)
Cl1—C2—C3—C4	178.9 (2)	C9—C8—C13—C12	−2.5 (3)
C2—C3—C4—C5	−0.3 (4)	C7—C8—C13—C12	177.57 (18)
C3—C4—C5—C6	0.3 (4)	O3—C7—N1—S1	4.7 (3)
C4—C5—C6—C1	0.4 (4)	C8—C7—N1—S1	−176.87 (13)
C2—C1—C6—C5	−0.9 (3)	C7—N1—S1—O1	50.47 (18)
S1—C1—C6—C5	175.69 (18)	C7—N1—S1—O2	178.25 (15)
O3—C7—C8—C13	27.9 (3)	C7—N1—S1—C1	−66.46 (17)
N1—C7—C8—C13	−150.47 (17)	C2—C1—S1—O1	179.10 (16)
O3—C7—C8—C9	−152.07 (19)	C6—C1—S1—O1	2.64 (18)
N1—C7—C8—C9	29.6 (2)	C2—C1—S1—O2	48.88 (18)
C13—C8—C9—C10	1.4 (3)	C6—C1—S1—O2	−127.58 (15)
C7—C8—C9—C10	−178.59 (17)	C2—C1—S1—N1	−63.04 (18)
C8—C9—C10—C11	0.4 (3)	C6—C1—S1—N1	120.49 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.16 (2)	2.974 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (2)	2.16 (2)	2.974 (2)	176 (2)

Symmetry code: (i) .