N-(3-Chloro-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

In the mol-ecule of the title compound, C(14)H(14)ClNO(2)S, the N-H bond is in a syn position with respect to the meta-Cl atom in the aniline ring. The mol-ecule is twisted about the N-S bond with a C-SO(2)-NH-C torsion angle of 44.55 (17)°. The two aromatic rings are inclined relative to each other by 66.2 (1)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into infinite chains parallel to the b axis.

Related literature

For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (1999 ▶), on N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-(ar­yl)aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Gowda et al. (2010 ▶); Perlovich et al. (2006 ▶). For the preparation of the title compound, See: Savitha & Gowda (2006 ▶)

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 9.0385 (7) Å

b = 9.7830 (7) Å

c = 15.897 (1) Å

β = 97.284 (7)°

V = 1394.33 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.44 × 0.40 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.837, T max = 0.877

5245 measured reflections

2841 independent reflections

2438 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.06

2841 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.36 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 datablock(s) I, global. DOI: 10.1107/S1600536811029400/bt5582sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029400/bt5582Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029400/bt5582Isup3.cml

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2954 reflections
a = 9.0385 (7) Å	θ = 2.6–27.8°
b = 9.7830 (7) Å	µ = 0.42 mm−1
c = 15.897 (1) Å	T = 293 K
β = 97.284 (7)°	Prism, colourless
V = 1394.33 (17) Å3	0.44 × 0.40 × 0.32 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2841 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
graphite	Rint = 0.009
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→5
Tmin = 0.837, Tmax = 0.877	k = −12→5
5245 measured reflections	l = −19→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.5258P] where P = (Fo2 + 2Fc2)/3
2841 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.36 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	0.89077 (18)	0.14785 (17)	0.62875 (11)	0.0313 (4)
C2	0.90726 (19)	0.19319 (18)	0.54672 (11)	0.0359 (4)
C3	0.8365 (2)	0.1167 (2)	0.47948 (12)	0.0407 (4)
H3	0.8471	0.1439	0.4245	0.049*
C4	0.7512 (2)	0.0022 (2)	0.49045 (12)	0.0413 (4)
C5	0.7383 (2)	−0.0396 (2)	0.57271 (13)	0.0453 (5)
H5	0.6825	−0.1170	0.5816	0.054*
C6	0.8074 (2)	0.03244 (19)	0.64125 (12)	0.0385 (4)
H6	0.7980	0.0035	0.6960	0.046*
C7	0.73064 (18)	0.40051 (18)	0.70252 (11)	0.0328 (4)
C8	0.67615 (19)	0.50629 (19)	0.64977 (12)	0.0371 (4)
H8	0.7410	0.5643	0.6259	0.045*
C9	0.5229 (2)	0.5243 (2)	0.63306 (12)	0.0402 (4)
C10	0.4248 (2)	0.4403 (2)	0.66791 (13)	0.0459 (5)
H10	0.3224	0.4542	0.6563	0.055*
C11	0.4810 (2)	0.3354 (2)	0.72028 (14)	0.0467 (5)
H11	0.4157	0.2778	0.7440	0.056*
C12	0.6335 (2)	0.3141 (2)	0.73829 (13)	0.0410 (4)
H12	0.6703	0.2430	0.7738	0.049*
C13	0.9916 (3)	0.3198 (2)	0.52740 (15)	0.0575 (6)
H13A	1.0910	0.3159	0.5569	0.069*
H13B	0.9415	0.3991	0.5455	0.069*
H13C	0.9960	0.3252	0.4675	0.069*
C14	0.6723 (3)	−0.0736 (3)	0.41520 (15)	0.0614 (6)
H14A	0.7398	−0.0875	0.3740	0.074*
H14B	0.5881	−0.0212	0.3904	0.074*
H14C	0.6387	−0.1606	0.4334	0.074*
N1	0.88789 (16)	0.38382 (16)	0.72030 (11)	0.0376 (4)
H1N	0.943 (2)	0.4465 (19)	0.7057 (13)	0.045*
O1	0.93966 (15)	0.15746 (14)	0.79211 (8)	0.0437 (3)
O2	1.12517 (14)	0.26929 (15)	0.71487 (9)	0.0469 (4)
Cl1	0.45335 (6)	0.65483 (6)	0.56450 (4)	0.06029 (19)
S1	0.97232 (4)	0.23553 (4)	0.72011 (3)	0.03353 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0310 (8)	0.0294 (8)	0.0333 (8)	0.0027 (6)	0.0027 (6)	0.0007 (7)
C2	0.0360 (9)	0.0325 (9)	0.0395 (9)	0.0025 (7)	0.0061 (7)	0.0050 (7)
C3	0.0440 (10)	0.0439 (10)	0.0339 (9)	0.0081 (8)	0.0037 (7)	0.0030 (8)
C4	0.0393 (9)	0.0408 (10)	0.0427 (10)	0.0060 (8)	0.0005 (8)	−0.0079 (8)
C5	0.0475 (11)	0.0349 (10)	0.0534 (12)	−0.0084 (8)	0.0064 (9)	−0.0023 (8)
C6	0.0422 (9)	0.0347 (9)	0.0386 (9)	−0.0038 (8)	0.0055 (7)	0.0041 (7)
C7	0.0273 (8)	0.0326 (8)	0.0384 (9)	−0.0005 (7)	0.0042 (7)	−0.0097 (7)
C8	0.0346 (9)	0.0342 (9)	0.0432 (10)	−0.0012 (7)	0.0074 (7)	−0.0047 (8)
C9	0.0373 (9)	0.0402 (10)	0.0419 (10)	0.0053 (8)	0.0006 (7)	−0.0080 (8)
C10	0.0284 (9)	0.0547 (12)	0.0540 (12)	0.0006 (8)	0.0032 (8)	−0.0118 (10)
C11	0.0338 (9)	0.0515 (12)	0.0563 (12)	−0.0088 (8)	0.0110 (9)	−0.0037 (10)
C12	0.0367 (9)	0.0386 (10)	0.0483 (11)	−0.0019 (8)	0.0077 (8)	0.0010 (8)
C13	0.0710 (14)	0.0507 (13)	0.0517 (13)	−0.0151 (11)	0.0110 (11)	0.0133 (10)
C14	0.0632 (14)	0.0641 (15)	0.0537 (13)	−0.0016 (12)	−0.0052 (11)	−0.0189 (12)
N1	0.0270 (7)	0.0298 (8)	0.0558 (10)	−0.0027 (6)	0.0037 (7)	−0.0041 (7)
O1	0.0500 (8)	0.0452 (8)	0.0348 (7)	0.0053 (6)	0.0014 (6)	0.0012 (6)
O2	0.0261 (6)	0.0531 (8)	0.0605 (9)	0.0008 (6)	0.0013 (6)	−0.0101 (7)
Cl1	0.0576 (3)	0.0566 (3)	0.0637 (4)	0.0163 (3)	−0.0036 (3)	0.0070 (3)
S1	0.0284 (2)	0.0337 (2)	0.0376 (2)	0.00265 (16)	0.00062 (16)	−0.00264 (17)

C1—C6	1.386 (2)	C9—C10	1.376 (3)
C1—C2	1.403 (2)	C9—Cl1	1.744 (2)
C1—S1	1.7655 (17)	C10—C11	1.378 (3)
C2—C3	1.392 (3)	C10—H10	0.9300
C2—C13	1.506 (3)	C11—C12	1.388 (3)
C3—C4	1.383 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.389 (3)	C13—H13A	0.9600
C4—C14	1.508 (3)	C13—H13B	0.9600
C5—C6	1.379 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.383 (3)	C14—H14C	0.9600
C7—C12	1.391 (3)	N1—S1	1.6394 (15)
C7—N1	1.423 (2)	N1—H1N	0.844 (15)
C8—C9	1.388 (2)	O1—S1	1.4375 (14)
C8—H8	0.9300	O2—S1	1.4331 (13)
C6—C1—C2	120.98 (16)	C11—C10—H10	120.6
C6—C1—S1	117.11 (13)	C10—C11—C12	121.16 (18)
C2—C1—S1	121.91 (13)	C10—C11—H11	119.4
C3—C2—C1	116.81 (16)	C12—C11—H11	119.4
C3—C2—C13	118.72 (17)	C11—C12—C7	119.09 (18)
C1—C2—C13	124.44 (18)	C11—C12—H12	120.5
C4—C3—C2	123.20 (17)	C7—C12—H12	120.5
C4—C3—H3	118.4	C2—C13—H13A	109.5
C2—C3—H3	118.4	C2—C13—H13B	109.5
C3—C4—C5	118.18 (17)	H13A—C13—H13B	109.5
C3—C4—C14	120.90 (19)	C2—C13—H13C	109.5
C5—C4—C14	120.92 (19)	H13A—C13—H13C	109.5
C6—C5—C4	120.60 (18)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C4—C14—H14A	109.5
C4—C5—H5	119.7	C4—C14—H14B	109.5
C5—C6—C1	120.23 (17)	H14A—C14—H14B	109.5
C5—C6—H6	119.9	C4—C14—H14C	109.5
C1—C6—H6	119.9	H14A—C14—H14C	109.5
C8—C7—C12	120.54 (16)	H14B—C14—H14C	109.5
C8—C7—N1	118.44 (16)	C7—N1—S1	123.69 (12)
C12—C7—N1	121.01 (17)	C7—N1—H1N	118.4 (15)
C7—C8—C9	118.76 (17)	S1—N1—H1N	110.5 (15)
C7—C8—H8	120.6	O2—S1—O1	117.75 (9)
C9—C8—H8	120.6	O2—S1—N1	104.39 (8)
C10—C9—C8	121.73 (18)	O1—S1—N1	109.03 (8)
C10—C9—Cl1	119.26 (15)	O2—S1—C1	111.66 (8)
C8—C9—Cl1	119.00 (15)	O1—S1—C1	106.89 (8)
C9—C10—C11	118.72 (17)	N1—S1—C1	106.59 (8)
C9—C10—H10	120.6
C6—C1—C2—C3	−0.1 (3)	C8—C9—C10—C11	−0.4 (3)
S1—C1—C2—C3	−179.26 (13)	Cl1—C9—C10—C11	178.36 (15)
C6—C1—C2—C13	177.94 (19)	C9—C10—C11—C12	0.3 (3)
S1—C1—C2—C13	−1.2 (3)	C10—C11—C12—C7	−0.1 (3)
C1—C2—C3—C4	1.0 (3)	C8—C7—C12—C11	0.0 (3)
C13—C2—C3—C4	−177.20 (19)	N1—C7—C12—C11	179.00 (17)
C2—C3—C4—C5	−1.3 (3)	C8—C7—N1—S1	−136.09 (15)
C2—C3—C4—C14	177.68 (18)	C12—C7—N1—S1	44.9 (2)
C3—C4—C5—C6	0.8 (3)	C7—N1—S1—O2	162.85 (15)
C14—C4—C5—C6	−178.21 (19)	C7—N1—S1—O1	−70.50 (17)
C4—C5—C6—C1	0.0 (3)	C7—N1—S1—C1	44.55 (17)
C2—C1—C6—C5	−0.3 (3)	C6—C1—S1—O2	133.91 (14)
S1—C1—C6—C5	178.83 (15)	C2—C1—S1—O2	−46.93 (17)
C12—C7—C8—C9	−0.2 (3)	C6—C1—S1—O1	3.82 (16)
N1—C7—C8—C9	−179.16 (16)	C2—C1—S1—O1	−177.03 (14)
C7—C8—C9—C10	0.4 (3)	C6—C1—S1—N1	−112.67 (14)
C7—C8—C9—Cl1	−178.42 (13)	C2—C1—S1—N1	66.48 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.32 (2)	3.117 (2)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.32 (2)	3.117 (2)	158 (2)

Symmetry code: (i) .