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

In the title compound, C(14)H(12)ClNO(3)S, the N-H bond in the C-SO(2)-NH-C(O) segment is anti to the C=O bond. Further, the C=O bond and the meta-Cl atom in the benzoyl ring are also anti to each other. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 72.4 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O 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: Bowes et al. (2003 ▶); Gowda et al. (2004 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2010 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C14H12ClNO3S

M = 309.76

Monoclinic,

a = 18.043 (2) Å

b = 12.046 (1) Å

c = 15.596 (2) Å

β = 118.77 (2)°

V = 2971.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.40 × 0.36 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.856, T max = 0.882

5996 measured reflections

3024 independent reflections

2463 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.03

3024 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.64 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD); data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶; 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/S1600536811050574/bt5728sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050574/bt5728Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050574/bt5728Isup3.cml

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

C14H12ClNO3S	F(000) = 1280
Mr = 309.76	Dx = 1.385 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3176 reflections
a = 18.043 (2) Å	θ = 2.8–27.8°
b = 12.046 (1) Å	µ = 0.40 mm−1
c = 15.596 (2) Å	T = 293 K
β = 118.77 (2)°	Prism, colourless
V = 2971.3 (6) Å3	0.40 × 0.36 × 0.32 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	3024 independent reflections
Radiation source: fine-focus sealed tube	2463 reflections with I > 2σ(I)
graphite	Rint = 0.012
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 = −22→18
Tmin = 0.856, Tmax = 0.882	k = −15→11
5996 measured reflections	l = −18→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0488P)2 + 4.0385P] where P = (Fo2 + 2Fc2)/3
3024 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.64 e Å−3

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	0.34287 (11)	0.11403 (15)	0.87322 (14)	0.0349 (4)
C2	0.29479 (13)	0.18523 (18)	0.79536 (16)	0.0449 (5)
C3	0.30275 (17)	0.1707 (2)	0.71180 (18)	0.0604 (6)
H3	0.2716	0.2161	0.6580	0.072*
C4	0.35502 (18)	0.0918 (2)	0.70565 (19)	0.0627 (7)
H4	0.3591	0.0854	0.6486	0.075*
C5	0.40121 (16)	0.0224 (2)	0.78294 (19)	0.0546 (6)
H5	0.4363	−0.0312	0.7785	0.065*
C6	0.39508 (13)	0.03297 (18)	0.86754 (16)	0.0434 (5)
H6	0.4257	−0.0139	0.9203	0.052*
C7	0.22402 (13)	−0.03082 (17)	0.94079 (16)	0.0418 (5)
C8	0.13770 (14)	−0.06030 (18)	0.92343 (16)	0.0451 (5)
C9	0.07257 (14)	0.0159 (2)	0.89365 (18)	0.0535 (6)
H9	0.0814	0.0905	0.8859	0.064*
C10	−0.00629 (16)	−0.0220 (3)	0.8757 (2)	0.0736 (8)
C11	−0.0197 (2)	−0.1309 (3)	0.8889 (3)	0.0970 (12)
H11	−0.0729	−0.1545	0.8770	0.116*
C12	0.0461 (2)	−0.2054 (3)	0.9201 (3)	0.0981 (12)
H12	0.0372	−0.2793	0.9298	0.118*
C13	0.12381 (17)	−0.1717 (2)	0.9368 (2)	0.0633 (7)
H13	0.1678	−0.2227	0.9571	0.076*
C14	0.23804 (18)	0.2758 (2)	0.7967 (2)	0.0657 (7)
H14A	0.2719	0.3353	0.8380	0.079*
H14B	0.2025	0.2469	0.8214	0.079*
H14C	0.2036	0.3032	0.7314	0.079*
N1	0.24872 (11)	0.07910 (15)	0.96409 (14)	0.0425 (4)
H1N	0.2195 (14)	0.1279 (17)	0.9688 (18)	0.051*
O1	0.40644 (10)	0.05491 (15)	1.05526 (11)	0.0546 (4)
O2	0.34229 (10)	0.23938 (13)	1.01017 (13)	0.0547 (4)
O3	0.27146 (10)	−0.09871 (13)	0.93618 (14)	0.0578 (4)
Cl1	−0.08922 (5)	0.07097 (11)	0.83538 (9)	0.1187 (4)
S1	0.34256 (3)	0.12455 (4)	0.98556 (4)	0.03864 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0307 (9)	0.0335 (10)	0.0424 (10)	−0.0031 (8)	0.0192 (8)	−0.0026 (8)
C2	0.0401 (11)	0.0408 (11)	0.0523 (12)	0.0002 (9)	0.0210 (10)	0.0047 (10)
C3	0.0678 (16)	0.0615 (15)	0.0487 (13)	0.0021 (13)	0.0255 (12)	0.0117 (12)
C4	0.0773 (18)	0.0704 (17)	0.0510 (14)	−0.0068 (14)	0.0393 (13)	−0.0077 (13)
C5	0.0567 (14)	0.0533 (14)	0.0659 (15)	0.0006 (11)	0.0393 (12)	−0.0115 (12)
C6	0.0397 (11)	0.0412 (11)	0.0517 (12)	0.0025 (9)	0.0239 (9)	−0.0007 (9)
C7	0.0449 (11)	0.0368 (11)	0.0473 (11)	−0.0006 (9)	0.0251 (10)	−0.0003 (9)
C8	0.0448 (12)	0.0423 (12)	0.0512 (12)	−0.0074 (9)	0.0254 (10)	−0.0072 (10)
C9	0.0428 (12)	0.0514 (13)	0.0631 (14)	−0.0037 (10)	0.0229 (11)	−0.0074 (11)
C10	0.0432 (14)	0.092 (2)	0.0811 (19)	−0.0048 (14)	0.0263 (13)	−0.0196 (17)
C11	0.0587 (18)	0.090 (2)	0.149 (3)	−0.0355 (18)	0.055 (2)	−0.034 (2)
C12	0.093 (3)	0.0636 (19)	0.155 (4)	−0.0324 (19)	0.073 (3)	−0.015 (2)
C13	0.0608 (15)	0.0442 (13)	0.092 (2)	−0.0093 (12)	0.0422 (15)	−0.0075 (13)
C14	0.0622 (16)	0.0524 (14)	0.0783 (18)	0.0205 (13)	0.0304 (14)	0.0163 (13)
N1	0.0388 (9)	0.0374 (9)	0.0605 (11)	−0.0007 (7)	0.0312 (9)	−0.0054 (8)
O1	0.0428 (8)	0.0729 (11)	0.0445 (8)	0.0079 (8)	0.0182 (7)	0.0070 (8)
O2	0.0522 (9)	0.0466 (9)	0.0766 (11)	−0.0129 (7)	0.0401 (9)	−0.0226 (8)
O3	0.0557 (10)	0.0395 (8)	0.0884 (13)	0.0041 (7)	0.0428 (9)	−0.0047 (8)
Cl1	0.0500 (4)	0.1486 (10)	0.1396 (9)	0.0240 (5)	0.0313 (5)	−0.0175 (7)
S1	0.0337 (3)	0.0404 (3)	0.0455 (3)	−0.0024 (2)	0.0219 (2)	−0.0056 (2)

C1—C6	1.389 (3)	C9—C10	1.388 (3)
C1—C2	1.396 (3)	C9—H9	0.9300
C1—S1	1.759 (2)	C10—C11	1.368 (5)
C2—C3	1.389 (3)	C10—Cl1	1.727 (3)
C2—C14	1.503 (3)	C11—C12	1.376 (5)
C3—C4	1.375 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.359 (4)
C4—C5	1.370 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.382 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O3	1.211 (2)	N1—S1	1.6532 (17)
C7—N1	1.389 (3)	N1—H1N	0.816 (16)
C7—C8	1.490 (3)	O1—S1	1.4170 (17)
C8—C9	1.384 (3)	O2—S1	1.4361 (16)
C8—C13	1.399 (3)
C6—C1—C2	122.21 (19)	C11—C10—C9	121.5 (3)
C6—C1—S1	116.20 (16)	C11—C10—Cl1	119.5 (2)
C2—C1—S1	121.57 (15)	C9—C10—Cl1	119.0 (3)
C3—C2—C1	115.9 (2)	C10—C11—C12	119.6 (3)
C3—C2—C14	118.8 (2)	C10—C11—H11	120.2
C1—C2—C14	125.2 (2)	C12—C11—H11	120.2
C4—C3—C2	122.4 (2)	C13—C12—C11	120.5 (3)
C4—C3—H3	118.8	C13—C12—H12	119.7
C2—C3—H3	118.8	C11—C12—H12	119.7
C5—C4—C3	120.5 (2)	C12—C13—C8	120.0 (3)
C5—C4—H4	119.8	C12—C13—H13	120.0
C3—C4—H4	119.8	C8—C13—H13	120.0
C4—C5—C6	119.3 (2)	C2—C14—H14A	109.5
C4—C5—H5	120.3	C2—C14—H14B	109.5
C6—C5—H5	120.3	H14A—C14—H14B	109.5
C5—C6—C1	119.6 (2)	C2—C14—H14C	109.5
C5—C6—H6	120.2	H14A—C14—H14C	109.5
C1—C6—H6	120.2	H14B—C14—H14C	109.5
O3—C7—N1	120.84 (19)	C7—N1—S1	122.50 (14)
O3—C7—C8	122.37 (19)	C7—N1—H1N	124.8 (18)
N1—C7—C8	116.78 (18)	S1—N1—H1N	112.7 (18)
C9—C8—C13	120.2 (2)	O1—S1—O2	118.13 (11)
C9—C8—C7	123.2 (2)	O1—S1—N1	109.57 (10)
C13—C8—C7	116.6 (2)	O2—S1—N1	103.78 (9)
C8—C9—C10	118.1 (2)	O1—S1—C1	109.27 (9)
C8—C9—H9	120.9	O2—S1—C1	109.73 (10)
C10—C9—H9	120.9	N1—S1—C1	105.56 (9)
C6—C1—C2—C3	−0.5 (3)	C8—C9—C10—Cl1	−178.3 (2)
S1—C1—C2—C3	177.92 (17)	C9—C10—C11—C12	−0.6 (6)
C6—C1—C2—C14	−179.0 (2)	Cl1—C10—C11—C12	179.4 (3)
S1—C1—C2—C14	−0.6 (3)	C10—C11—C12—C13	−0.6 (6)
C1—C2—C3—C4	−0.4 (4)	C11—C12—C13—C8	0.7 (6)
C14—C2—C3—C4	178.2 (3)	C9—C8—C13—C12	0.3 (4)
C2—C3—C4—C5	0.8 (4)	C7—C8—C13—C12	−178.5 (3)
C3—C4—C5—C6	−0.3 (4)	O3—C7—N1—S1	0.7 (3)
C4—C5—C6—C1	−0.5 (3)	C8—C7—N1—S1	179.90 (15)
C2—C1—C6—C5	0.9 (3)	C7—N1—S1—O1	−50.7 (2)
S1—C1—C6—C5	−177.54 (17)	C7—N1—S1—O2	−177.71 (18)
O3—C7—C8—C9	−156.0 (2)	C7—N1—S1—C1	66.88 (19)
N1—C7—C8—C9	24.8 (3)	C6—C1—S1—O1	7.75 (19)
O3—C7—C8—C13	22.7 (3)	C2—C1—S1—O1	−170.73 (16)
N1—C7—C8—C13	−156.5 (2)	C6—C1—S1—O2	138.74 (16)
C13—C8—C9—C10	−1.4 (4)	C2—C1—S1—O2	−39.75 (19)
C7—C8—C9—C10	177.3 (2)	C6—C1—S1—N1	−110.00 (16)
C8—C9—C10—C11	1.6 (4)	C2—C1—S1—N1	71.51 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.06 (2)	2.876 (2)	174 (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)	2.06 (2)	2.876 (2)	174 (2)

Symmetry code: (i) .