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

In the title compound, C(14)H(14)ClNO(2)S, the N-H bond points away from the dimethyl-phenyl ring plane. The mol-ecule is twisted at the S atom, with a C-SO(2)-NH-C torsion angle of -75.5 (2)°. The two aromatic rings are tilted relative to each other by 63.3 (1)°. The Cl atom on the chloro-benzene ring is disordered over two sites with site-occupation factors of 0.59 (3) and 0.41 (3), respectively. The crystal structure features inversion-related dimers linked by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶), on N-(ar­yl)aryl­sulfonamides, see: Shakuntala et al. (2011 ▶) and on N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 8.0493 (7) Å

b = 11.4980 (9) Å

c = 15.505 (1) Å

β = 90.512 (8)°

V = 1434.94 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.40 × 0.38 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.854, T max = 0.860

5316 measured reflections

2920 independent reflections

2299 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.04

2920 reflections

188 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 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/S160053681101960X/sj5151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101960X/sj5151Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101960X/sj5151Isup3.cml

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.369 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2311 reflections
a = 8.0493 (7) Å	θ = 2.6–27.8°
b = 11.4980 (9) Å	µ = 0.41 mm−1
c = 15.505 (1) Å	T = 293 K
β = 90.512 (8)°	Prism, colourless
V = 1434.94 (19) Å3	0.40 × 0.38 × 0.38 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2920 independent reflections
Radiation source: fine-focus sealed tube	2299 reflections with I > 2σ(I)
graphite	Rint = 0.012
ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→9
Tmin = 0.854, Tmax = 0.860	k = −10→14
5316 measured reflections	l = −19→11

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) = 0.110	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.340P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2920 reflections	Δρmax = 0.21 e Å−3
188 parameters	Δρmin = −0.28 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.019 (2)

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
C1	0.0604 (2)	0.32592 (15)	0.64405 (11)	0.0432 (4)
C2	0.1241 (3)	0.24160 (19)	0.69852 (14)	0.0618 (6)
H2	0.2380	0.2366	0.7085	0.074*
C3	0.0167 (4)	0.1645 (2)	0.73809 (15)	0.0796 (7)
H3	0.0575	0.1067	0.7745	0.096*
C4	−0.1506 (4)	0.1748 (2)	0.72276 (14)	0.0746 (7)
C5	−0.2145 (3)	0.2570 (2)	0.66818 (15)	0.0679 (6)
H5	−0.3284	0.2615	0.6583	0.082*
C6	−0.1083 (2)	0.33272 (18)	0.62807 (13)	0.0535 (5)
H6	−0.1499	0.3885	0.5902	0.064*
C7	0.3261 (2)	0.29199 (15)	0.47078 (11)	0.0388 (4)
C8	0.2602 (2)	0.18976 (17)	0.43790 (12)	0.0467 (4)
C9	0.3707 (2)	0.10523 (17)	0.40995 (14)	0.0533 (5)
H9	0.3280	0.0361	0.3878	0.064*
C10	0.5409 (2)	0.11919 (19)	0.41361 (13)	0.0515 (5)
C11	0.6010 (2)	0.2211 (2)	0.44796 (14)	0.0581 (5)
H11	0.7152	0.2320	0.4527	0.070*
C12	0.4960 (2)	0.30731 (18)	0.47550 (13)	0.0508 (5)
H12	0.5395	0.3763	0.4974	0.061*
C13	0.0765 (2)	0.1693 (2)	0.43064 (19)	0.0756 (7)
H13A	0.0278	0.2267	0.3932	0.091*
H13B	0.0276	0.1748	0.4867	0.091*
H13C	0.0564	0.0932	0.4073	0.091*
C14	0.6541 (3)	0.0252 (2)	0.37959 (17)	0.0733 (7)
H14A	0.6704	0.0365	0.3189	0.088*
H14B	0.6044	−0.0495	0.3891	0.088*
H14C	0.7593	0.0290	0.4091	0.088*
N1	0.22067 (18)	0.38712 (14)	0.49490 (10)	0.0422 (4)
H1N	0.135 (2)	0.3982 (17)	0.4655 (12)	0.051*
O1	0.34964 (17)	0.42218 (13)	0.63764 (9)	0.0598 (4)
O2	0.10520 (16)	0.53494 (11)	0.58902 (9)	0.0535 (4)
Cl1A	−0.3124 (18)	0.0933 (11)	0.7734 (2)	0.086 (2)	0.59 (3)
Cl1B	−0.241 (3)	0.0629 (10)	0.7776 (4)	0.089 (3)	0.41 (3)
S1	0.19347 (5)	0.42678 (4)	0.59428 (3)	0.04223 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0585 (11)	0.0365 (9)	0.0347 (9)	0.0036 (8)	0.0073 (8)	−0.0025 (7)
C2	0.0819 (15)	0.0539 (12)	0.0495 (12)	0.0129 (11)	0.0006 (10)	0.0053 (10)
C3	0.1420 (18)	0.0483 (13)	0.0485 (12)	−0.0011 (15)	0.0017 (14)	0.0120 (10)
C4	0.1281 (16)	0.0603 (14)	0.0356 (11)	−0.0405 (15)	0.0183 (12)	−0.0085 (10)
C5	0.0748 (15)	0.0753 (15)	0.0539 (13)	−0.0250 (12)	0.0108 (11)	−0.0042 (12)
C6	0.0553 (11)	0.0544 (12)	0.0508 (11)	−0.0032 (9)	0.0047 (9)	0.0063 (9)
C7	0.0369 (8)	0.0433 (10)	0.0363 (9)	0.0056 (7)	0.0035 (7)	0.0014 (7)
C8	0.0362 (9)	0.0505 (11)	0.0533 (11)	0.0013 (8)	0.0010 (8)	−0.0058 (9)
C9	0.0505 (11)	0.0487 (11)	0.0609 (13)	0.0032 (9)	0.0015 (9)	−0.0143 (9)
C10	0.0457 (10)	0.0594 (12)	0.0495 (11)	0.0153 (9)	0.0033 (8)	−0.0033 (9)
C11	0.0338 (9)	0.0745 (15)	0.0662 (13)	0.0062 (9)	0.0009 (9)	−0.0114 (11)
C12	0.0382 (9)	0.0549 (11)	0.0592 (12)	−0.0031 (8)	0.0032 (8)	−0.0103 (10)
C13	0.0415 (11)	0.0741 (16)	0.111 (2)	−0.0044 (10)	0.0007 (12)	−0.0314 (15)
C14	0.0639 (13)	0.0792 (17)	0.0769 (16)	0.0278 (12)	0.0067 (11)	−0.0135 (13)
N1	0.0404 (8)	0.0463 (8)	0.0400 (8)	0.0099 (7)	0.0027 (6)	0.0002 (7)
O1	0.0516 (8)	0.0712 (10)	0.0565 (9)	0.0007 (7)	−0.0053 (6)	−0.0125 (7)
O2	0.0587 (8)	0.0366 (7)	0.0655 (9)	0.0055 (6)	0.0118 (7)	−0.0034 (6)
Cl1A	0.123 (4)	0.088 (3)	0.0468 (7)	−0.057 (3)	0.0104 (13)	0.0026 (10)
Cl1B	0.135 (7)	0.076 (2)	0.0556 (12)	−0.045 (3)	0.015 (2)	0.0044 (13)
S1	0.0442 (3)	0.0389 (3)	0.0437 (3)	0.00330 (18)	0.00397 (18)	−0.00408 (19)

C1—C6	1.380 (3)	C9—C10	1.380 (3)
C1—C2	1.382 (3)	C9—H9	0.9300
C1—S1	1.7613 (18)	C10—C11	1.374 (3)
C2—C3	1.385 (3)	C10—C14	1.511 (3)
C2—H2	0.9300	C11—C12	1.373 (3)
C3—C4	1.371 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.366 (4)	C13—H13A	0.9600
C4—Cl1B	1.710 (5)	C13—H13B	0.9600
C4—Cl1A	1.792 (5)	C13—H13C	0.9600
C5—C6	1.373 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C12	1.380 (2)	N1—S1	1.6236 (16)
C7—C8	1.385 (3)	N1—H1N	0.831 (15)
C7—N1	1.436 (2)	O1—S1	1.4212 (15)
C8—C9	1.389 (3)	O2—S1	1.4343 (13)
C8—C13	1.501 (3)
C6—C1—C2	120.59 (19)	C11—C10—C9	117.48 (17)
C6—C1—S1	119.02 (14)	C11—C10—C14	122.26 (19)
C2—C1—S1	120.39 (16)	C9—C10—C14	120.3 (2)
C1—C2—C3	119.3 (2)	C12—C11—C10	121.37 (17)
C1—C2—H2	120.3	C12—C11—H11	119.3
C3—C2—H2	120.3	C10—C11—H11	119.3
C4—C3—C2	118.9 (2)	C11—C12—C7	120.26 (18)
C4—C3—H3	120.5	C11—C12—H12	119.9
C2—C3—H3	120.5	C7—C12—H12	119.9
C5—C4—C3	122.1 (2)	C8—C13—H13A	109.5
C5—C4—Cl1B	131.9 (10)	C8—C13—H13B	109.5
C3—C4—Cl1B	105.8 (10)	H13A—C13—H13B	109.5
C5—C4—Cl1A	111.2 (6)	C8—C13—H13C	109.5
C3—C4—Cl1A	126.6 (6)	H13A—C13—H13C	109.5
Cl1B—C4—Cl1A	22.0 (4)	H13B—C13—H13C	109.5
C4—C5—C6	119.1 (2)	C10—C14—H14A	109.5
C4—C5—H5	120.4	C10—C14—H14B	109.5
C6—C5—H5	120.4	H14A—C14—H14B	109.5
C5—C6—C1	119.9 (2)	C10—C14—H14C	109.5
C5—C6—H6	120.1	H14A—C14—H14C	109.5
C1—C6—H6	120.1	H14B—C14—H14C	109.5
C12—C7—C8	120.24 (16)	C7—N1—S1	123.10 (12)
C12—C7—N1	118.46 (16)	C7—N1—H1N	117.4 (14)
C8—C7—N1	121.16 (15)	S1—N1—H1N	111.2 (14)
C7—C8—C9	117.70 (16)	O1—S1—O2	119.66 (9)
C7—C8—C13	122.31 (17)	O1—S1—N1	108.20 (8)
C9—C8—C13	119.98 (18)	O2—S1—N1	105.10 (8)
C10—C9—C8	122.93 (19)	O1—S1—C1	107.88 (9)
C10—C9—H9	118.5	O2—S1—C1	107.04 (8)
C8—C9—H9	118.5	N1—S1—C1	108.58 (8)
C6—C1—C2—C3	−0.9 (3)	C8—C9—C10—C11	1.1 (3)
S1—C1—C2—C3	178.87 (16)	C8—C9—C10—C14	−178.1 (2)
C1—C2—C3—C4	−0.7 (3)	C9—C10—C11—C12	−1.7 (3)
C2—C3—C4—C5	1.5 (4)	C14—C10—C11—C12	177.5 (2)
C2—C3—C4—Cl1B	177.4 (3)	C10—C11—C12—C7	1.4 (3)
C2—C3—C4—Cl1A	−174.5 (4)	C8—C7—C12—C11	−0.3 (3)
C3—C4—C5—C6	−0.8 (4)	N1—C7—C12—C11	−175.95 (18)
Cl1B—C4—C5—C6	−175.4 (4)	C12—C7—N1—S1	−73.9 (2)
Cl1A—C4—C5—C6	175.7 (3)	C8—C7—N1—S1	110.48 (18)
C4—C5—C6—C1	−0.8 (3)	C7—N1—S1—O1	41.30 (16)
C2—C1—C6—C5	1.6 (3)	C7—N1—S1—O2	170.21 (14)
S1—C1—C6—C5	−178.15 (16)	C7—N1—S1—C1	−75.53 (16)
C12—C7—C8—C9	−0.4 (3)	C6—C1—S1—O1	164.67 (15)
N1—C7—C8—C9	175.19 (17)	C2—C1—S1—O1	−15.08 (18)
C12—C7—C8—C13	−179.4 (2)	C6—C1—S1—O2	34.68 (17)
N1—C7—C8—C13	−3.9 (3)	C2—C1—S1—O2	−145.06 (16)
C7—C8—C9—C10	−0.1 (3)	C6—C1—S1—N1	−78.29 (16)
C13—C8—C9—C10	179.0 (2)	C2—C1—S1—N1	101.96 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.24 (2)	3.052 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.24 (2)	3.052 (2)	165 (2)

Symmetry code: (i) .