N-(2-Chloro-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

In the title compound, C(14)H(14)ClNO(2)S, the conformation of the N-C bond in the C-SO(2)-NH-C segment has gauche torsions with respect to the S=O bonds. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of -54.9 (2)°. The sulfonyl and aniline benzene rings are rotated relative to each other by 75.7 (1)°. An intra-molecular N-H⋯Cl hydrogen bond is present. In the crystal, inter-molecular N-H⋯O hydrogen-bonding inter-actions are observed and the mol-ecules are packed into chains parallel to the b axis.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2009 ▶, 2010 ▶); Nirmala et al. (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Orthorhombic,

a = 10.574 (1) Å

b = 16.269 (2) Å

c = 16.859 (2) Å

V = 2900.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 299 K

0.38 × 0.34 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.862, T max = 0.909

18999 measured reflections

2922 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.05

2922 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.27 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/S1600536810015916/rz2441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015916/rz2441Isup2.hkl

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

C14H14ClNO2S	F(000) = 1232
Mr = 295.77	Dx = 1.355 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2348 reflections
a = 10.574 (1) Å	θ = 2.6–27.8°
b = 16.269 (2) Å	µ = 0.40 mm−1
c = 16.859 (2) Å	T = 299 K
V = 2900.2 (6) Å3	Prism, colourless
Z = 8	0.38 × 0.34 × 0.24 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2922 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
graphite	Rint = 0.026
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→13
Tmin = 0.862, Tmax = 0.909	k = −19→19
18999 measured reflections	l = −20→20

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0452P)2 + 1.1956P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
2922 reflections	Δρmax = 0.23 e Å−3
178 parameters	Δρmin = −0.27 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: 0.0063 (6)

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	0.31380 (18)	0.39372 (11)	0.32739 (11)	0.0470 (4)
C2	0.2828 (2)	0.47702 (12)	0.31522 (12)	0.0543 (5)
C3	0.3721 (2)	0.53467 (14)	0.33864 (15)	0.0707 (6)
H3	0.3530	0.5900	0.3318	0.085*
C4	0.4873 (3)	0.51455 (17)	0.37137 (16)	0.0809 (7)
C5	0.5148 (3)	0.43261 (18)	0.38187 (19)	0.0872 (8)
H5	0.5921	0.4175	0.4038	0.105*
C6	0.4290 (2)	0.37243 (15)	0.36013 (15)	0.0670 (6)
H6	0.4490	0.3173	0.3676	0.080*
C7	0.10341 (18)	0.31392 (11)	0.44692 (10)	0.0465 (4)
C8	0.0207 (2)	0.35953 (11)	0.49298 (11)	0.0499 (5)
C9	0.0269 (3)	0.35663 (14)	0.57551 (12)	0.0660 (6)
H9	−0.0305	0.3863	0.6059	0.079*
C10	0.1184 (3)	0.30960 (14)	0.61177 (12)	0.0712 (7)
H10	0.1237	0.3083	0.6668	0.085*
C11	0.2011 (3)	0.26496 (15)	0.56722 (13)	0.0687 (6)
H11	0.2633	0.2338	0.5921	0.082*
C12	0.1932 (2)	0.26568 (14)	0.48522 (12)	0.0629 (6)
H12	0.2485	0.2336	0.4555	0.076*
C13	0.1609 (2)	0.50496 (15)	0.27754 (16)	0.0766 (7)
H13A	0.0907	0.4846	0.3078	0.092*
H13B	0.1560	0.4841	0.2244	0.092*
H13C	0.1583	0.5639	0.2764	0.092*
C14	0.5812 (3)	0.5810 (2)	0.3941 (3)	0.1248 (13)
H14A	0.5396	0.6217	0.4260	0.150*
H14B	0.6140	0.6063	0.3470	0.150*
H14C	0.6494	0.5570	0.4237	0.150*
N1	0.09250 (16)	0.31599 (11)	0.36289 (9)	0.0538 (4)
H1N	0.0245 (14)	0.3331 (13)	0.3411 (12)	0.065*
O1	0.15450 (14)	0.32896 (10)	0.22493 (7)	0.0610 (4)
O2	0.27871 (14)	0.23745 (8)	0.31126 (9)	0.0625 (4)
Cl1	−0.09351 (6)	0.42128 (4)	0.44867 (3)	0.0714 (2)
S1	0.21116 (5)	0.31295 (3)	0.30076 (3)	0.04739 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0497 (11)	0.0479 (10)	0.0435 (9)	0.0042 (8)	0.0033 (8)	−0.0029 (8)
C2	0.0586 (12)	0.0515 (11)	0.0528 (11)	0.0071 (9)	0.0096 (9)	−0.0013 (9)
C3	0.0839 (17)	0.0502 (12)	0.0779 (16)	−0.0034 (12)	0.0141 (14)	−0.0051 (11)
C4	0.0782 (17)	0.0775 (17)	0.0872 (18)	−0.0189 (14)	−0.0004 (15)	−0.0105 (14)
C5	0.0599 (14)	0.0923 (19)	0.109 (2)	−0.0086 (14)	−0.0208 (15)	0.0019 (16)
C6	0.0587 (13)	0.0597 (13)	0.0825 (16)	0.0057 (11)	−0.0130 (12)	0.0024 (11)
C7	0.0548 (11)	0.0488 (10)	0.0358 (9)	−0.0121 (9)	−0.0039 (8)	0.0009 (8)
C8	0.0643 (12)	0.0432 (9)	0.0423 (9)	−0.0129 (9)	−0.0035 (9)	−0.0022 (8)
C9	0.0950 (18)	0.0603 (13)	0.0428 (11)	−0.0148 (12)	0.0070 (11)	−0.0098 (9)
C10	0.112 (2)	0.0645 (14)	0.0372 (10)	−0.0271 (14)	−0.0138 (12)	0.0084 (10)
C11	0.0886 (17)	0.0681 (14)	0.0494 (12)	−0.0103 (13)	−0.0191 (12)	0.0122 (10)
C12	0.0715 (14)	0.0687 (14)	0.0487 (11)	0.0044 (11)	−0.0093 (10)	0.0056 (10)
C13	0.0767 (16)	0.0623 (14)	0.0907 (18)	0.0212 (13)	−0.0013 (14)	0.0076 (12)
C14	0.110 (3)	0.110 (3)	0.154 (3)	−0.048 (2)	−0.006 (2)	−0.023 (2)
N1	0.0493 (10)	0.0769 (12)	0.0352 (8)	0.0021 (9)	−0.0043 (7)	0.0025 (8)
O1	0.0647 (9)	0.0840 (10)	0.0342 (7)	0.0007 (8)	−0.0022 (6)	−0.0054 (6)
O2	0.0747 (10)	0.0478 (8)	0.0650 (9)	0.0094 (7)	−0.0006 (8)	−0.0098 (6)
Cl1	0.0827 (4)	0.0706 (4)	0.0610 (3)	0.0138 (3)	−0.0051 (3)	−0.0124 (3)
S1	0.0538 (3)	0.0511 (3)	0.0372 (2)	0.0036 (2)	−0.0007 (2)	−0.00583 (18)

C1—C6	1.381 (3)	C9—C10	1.376 (3)
C1—C2	1.409 (3)	C9—H9	0.9300
C1—S1	1.7624 (19)	C10—C11	1.363 (3)
C2—C3	1.388 (3)	C10—H10	0.9300
C2—C13	1.508 (3)	C11—C12	1.385 (3)
C3—C4	1.377 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.376 (4)	C13—H13A	0.9600
C4—C14	1.518 (4)	C13—H13B	0.9600
C5—C6	1.385 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.385 (3)	C14—H14C	0.9600
C7—C12	1.391 (3)	N1—S1	1.6352 (17)
C7—N1	1.422 (2)	N1—H1N	0.854 (9)
C8—C9	1.394 (3)	O1—S1	1.4357 (14)
C8—Cl1	1.739 (2)	O2—S1	1.4319 (14)
C6—C1—C2	120.29 (19)	C9—C10—H10	119.9
C6—C1—S1	117.24 (16)	C10—C11—C12	120.5 (2)
C2—C1—S1	122.47 (15)	C10—C11—H11	119.8
C3—C2—C1	116.8 (2)	C12—C11—H11	119.8
C3—C2—C13	119.8 (2)	C11—C12—C7	120.6 (2)
C1—C2—C13	123.37 (19)	C11—C12—H12	119.7
C4—C3—C2	123.7 (2)	C7—C12—H12	119.7
C4—C3—H3	118.1	C2—C13—H13A	109.5
C2—C3—H3	118.1	C2—C13—H13B	109.5
C5—C4—C3	118.0 (2)	H13A—C13—H13B	109.5
C5—C4—C14	121.3 (3)	C2—C13—H13C	109.5
C3—C4—C14	120.7 (3)	H13A—C13—H13C	109.5
C4—C5—C6	120.8 (2)	H13B—C13—H13C	109.5
C4—C5—H5	119.6	C4—C14—H14A	109.5
C6—C5—H5	119.6	C4—C14—H14B	109.5
C1—C6—C5	120.4 (2)	H14A—C14—H14B	109.5
C1—C6—H6	119.8	C4—C14—H14C	109.5
C5—C6—H6	119.8	H14A—C14—H14C	109.5
C8—C7—C12	118.24 (17)	H14B—C14—H14C	109.5
C8—C7—N1	119.64 (17)	C7—N1—S1	125.12 (14)
C12—C7—N1	122.10 (18)	C7—N1—H1N	120.3 (16)
C7—C8—C9	120.8 (2)	S1—N1—H1N	112.4 (15)
C7—C8—Cl1	120.47 (14)	O2—S1—O1	118.28 (9)
C9—C8—Cl1	118.77 (17)	O2—S1—N1	109.24 (9)
C10—C9—C8	119.7 (2)	O1—S1—N1	104.16 (9)
C10—C9—H9	120.1	O2—S1—C1	107.52 (9)
C8—C9—H9	120.1	O1—S1—C1	110.40 (9)
C11—C10—C9	120.2 (2)	N1—S1—C1	106.67 (9)
C11—C10—H10	119.9
C6—C1—C2—C3	−0.9 (3)	Cl1—C8—C9—C10	−178.55 (16)
S1—C1—C2—C3	−179.84 (16)	C8—C9—C10—C11	−1.1 (3)
C6—C1—C2—C13	178.1 (2)	C9—C10—C11—C12	−0.7 (4)
S1—C1—C2—C13	−0.9 (3)	C10—C11—C12—C7	2.0 (4)
C1—C2—C3—C4	0.9 (3)	C8—C7—C12—C11	−1.4 (3)
C13—C2—C3—C4	−178.1 (2)	N1—C7—C12—C11	−179.9 (2)
C2—C3—C4—C5	−0.5 (4)	C8—C7—N1—S1	144.02 (16)
C2—C3—C4—C14	178.8 (3)	C12—C7—N1—S1	−37.6 (3)
C3—C4—C5—C6	0.0 (4)	C7—N1—S1—O2	61.07 (19)
C14—C4—C5—C6	−179.3 (3)	C7—N1—S1—O1	−171.66 (16)
C2—C1—C6—C5	0.5 (3)	C7—N1—S1—C1	−54.86 (19)
S1—C1—C6—C5	179.5 (2)	C6—C1—S1—O2	−6.68 (19)
C4—C5—C6—C1	0.0 (4)	C2—C1—S1—O2	172.29 (15)
C12—C7—C8—C9	−0.4 (3)	C6—C1—S1—O1	−137.03 (17)
N1—C7—C8—C9	178.06 (18)	C2—C1—S1—O1	41.94 (19)
C12—C7—C8—Cl1	179.82 (15)	C6—C1—S1—N1	110.40 (17)
N1—C7—C8—Cl1	−1.7 (2)	C2—C1—S1—N1	−70.63 (18)
C7—C8—C9—C10	1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.20 (1)	3.010 (2)	159 (2)
N1—H1N···Cl1	0.85 (1)	2.63 (2)	2.9822 (18)	106 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.20 (1)	3.010 (2)	159 (2)
N1—H1N⋯Cl1	0.85 (1)	2.63 (2)	2.9822 (18)	106 (2)

Symmetry code: (i) .