4-Chloro-N-(2,6-dimethyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(14)ClNO(2)S, the amido H atom orients itself away from both the ortho-methyl groups in the adjacent aromatic ring. The mol-ecule is twisted at the S atom with an C-SO(2)-NH-C torsion angle of -69.9 (2)°. The two aromatic rings are tilted relative to each other by 31.9 (1)°. In the crystal, the mol-ecules are packed into zigzag chains along the b axis via inter-molecular N-H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶), on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2008 ▶); Shakuntala et al. (2011 ▶) and on the oxidative strengths of N-chloro,N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Orthorhombic,

a = 7.3816 (4) Å

b = 10.2916 (7) Å

c = 18.312 (1) Å

V = 1391.13 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.40 × 0.28 × 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 = 0.850, T max = 0.906

5356 measured reflections

2767 independent reflections

2255 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.079

S = 1.02

2767 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1113 Friedel pairs

Flack parameter: 0.43 (7)

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/S160053681101717X/bq2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101717X/bq2299Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101717X/bq2299Isup3.cml

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.412 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1775 reflections
a = 7.3816 (4) Å	θ = 2.8–28.0°
b = 10.2916 (7) Å	µ = 0.42 mm−1
c = 18.312 (1) Å	T = 293 K
V = 1391.13 (14) Å3	Prism, colourless
Z = 4	0.40 × 0.28 × 0.24 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2767 independent reflections
Radiation source: fine-focus sealed tube	2255 reflections with I > 2σ(I)
graphite	Rint = 0.022
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→6
Tmin = 0.850, Tmax = 0.906	k = −12→10
5356 measured reflections	l = −22→17

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0326P)2 + 0.3144P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2767 reflections	Δρmax = 0.19 e Å−3
177 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1113 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.43 (7)

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
Cl1	0.42735 (14)	0.03948 (8)	−0.04544 (5)	0.0851 (3)
S1	0.96404 (8)	0.20494 (6)	0.19969 (4)	0.04077 (16)
O1	0.9231 (3)	0.33512 (15)	0.22176 (9)	0.0502 (5)
O2	1.1425 (2)	0.1712 (2)	0.17729 (11)	0.0606 (6)
N1	0.9167 (3)	0.11125 (19)	0.26858 (12)	0.0389 (5)
H1N	0.950 (3)	0.0356 (17)	0.2645 (14)	0.047*
C1	0.8156 (3)	0.1660 (2)	0.12743 (13)	0.0375 (6)
C2	0.8780 (4)	0.0962 (2)	0.06798 (14)	0.0479 (7)
H2	1.0000	0.0745	0.0642	0.057*
C3	0.7573 (4)	0.0591 (3)	0.01437 (15)	0.0568 (8)
H3	0.7974	0.0119	−0.0258	0.068*
C4	0.5788 (4)	0.0917 (3)	0.02047 (14)	0.0513 (7)
C5	0.5165 (4)	0.1648 (3)	0.07828 (15)	0.0524 (7)
H5	0.3949	0.1880	0.0811	0.063*
C6	0.6357 (3)	0.2032 (3)	0.13178 (14)	0.0450 (6)
H6	0.5958	0.2539	0.1706	0.054*
C7	0.7516 (3)	0.1254 (2)	0.30961 (13)	0.0357 (5)
C8	0.6035 (3)	0.0460 (2)	0.29430 (14)	0.0424 (6)
C9	0.4451 (4)	0.0670 (3)	0.33397 (15)	0.0560 (7)
H9	0.3433	0.0166	0.3244	0.067*
C10	0.4376 (4)	0.1614 (3)	0.38707 (17)	0.0620 (8)
H10	0.3302	0.1752	0.4124	0.074*
C11	0.5853 (4)	0.2345 (3)	0.40283 (14)	0.0555 (8)
H11	0.5782	0.2965	0.4397	0.067*
C12	0.7464 (4)	0.2189 (3)	0.36519 (13)	0.0433 (6)
C13	0.6103 (4)	−0.0616 (3)	0.23877 (15)	0.0573 (7)
H13A	0.6806	−0.0340	0.1975	0.069*
H13B	0.4896	−0.0823	0.2232	0.069*
H13C	0.6652	−0.1371	0.2602	0.069*
C14	0.9069 (4)	0.2998 (3)	0.38620 (16)	0.0642 (8)
H14A	1.0162	0.2550	0.3730	0.077*
H14B	0.9055	0.3145	0.4380	0.077*
H14C	0.9017	0.3816	0.3611	0.077*

	U11	U22	U33	U12	U13	U23
Cl1	0.1151 (8)	0.0671 (5)	0.0730 (6)	−0.0104 (5)	−0.0493 (5)	0.0049 (4)
S1	0.0373 (3)	0.0394 (3)	0.0457 (3)	−0.0063 (3)	0.0044 (3)	−0.0015 (3)
O1	0.0686 (12)	0.0340 (9)	0.0480 (10)	−0.0116 (9)	0.0022 (9)	0.0000 (8)
O2	0.0365 (10)	0.0769 (15)	0.0684 (13)	−0.0049 (9)	0.0078 (8)	−0.0039 (11)
N1	0.0376 (12)	0.0320 (11)	0.0470 (12)	0.0027 (9)	0.0007 (9)	0.0018 (10)
C1	0.0416 (14)	0.0321 (13)	0.0389 (13)	−0.0015 (11)	0.0030 (11)	0.0013 (11)
C2	0.0529 (16)	0.0410 (15)	0.0498 (16)	0.0081 (12)	0.0069 (13)	−0.0040 (13)
C3	0.084 (2)	0.0459 (17)	0.0407 (15)	0.0074 (17)	0.0016 (15)	−0.0071 (13)
C4	0.067 (2)	0.0398 (15)	0.0468 (16)	−0.0057 (14)	−0.0123 (14)	0.0078 (13)
C5	0.0452 (15)	0.0573 (17)	0.0548 (16)	0.0013 (13)	−0.0048 (13)	0.0073 (14)
C6	0.0449 (15)	0.0453 (15)	0.0446 (14)	0.0040 (13)	0.0062 (12)	−0.0026 (13)
C7	0.0363 (12)	0.0346 (13)	0.0360 (13)	−0.0003 (10)	−0.0034 (10)	0.0064 (11)
C8	0.0429 (13)	0.0386 (14)	0.0456 (14)	−0.0053 (11)	−0.0042 (12)	0.0092 (12)
C9	0.0406 (15)	0.0624 (19)	0.0651 (17)	−0.0106 (15)	−0.0001 (14)	0.0153 (16)
C10	0.0554 (18)	0.0652 (19)	0.0655 (19)	0.0109 (16)	0.0184 (15)	0.0144 (16)
C11	0.075 (2)	0.0508 (17)	0.0405 (15)	0.0094 (15)	0.0100 (14)	0.0007 (13)
C12	0.0569 (16)	0.0379 (14)	0.0353 (13)	−0.0015 (13)	−0.0050 (12)	0.0054 (11)
C13	0.0647 (18)	0.0464 (17)	0.0607 (17)	−0.0199 (14)	−0.0066 (15)	−0.0008 (14)
C14	0.080 (2)	0.0604 (19)	0.0521 (16)	−0.0142 (18)	−0.0114 (15)	−0.0103 (16)

Cl1—C4	1.731 (3)	C7—C8	1.393 (3)
S1—O2	1.4228 (18)	C7—C12	1.401 (3)
S1—O1	1.4316 (17)	C8—C9	1.393 (4)
S1—N1	1.626 (2)	C8—C13	1.504 (3)
S1—C1	1.764 (2)	C9—C10	1.375 (4)
N1—C7	1.440 (3)	C9—H9	0.9300
N1—H1N	0.818 (16)	C10—C11	1.356 (4)
C1—C2	1.383 (3)	C10—H10	0.9300
C1—C6	1.385 (3)	C11—C12	1.383 (4)
C2—C3	1.380 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C14	1.498 (4)
C3—C4	1.364 (4)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.378 (4)	C13—H13C	0.9600
C5—C6	1.375 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O2—S1—O1	120.37 (12)	C12—C7—N1	118.2 (2)
O2—S1—N1	106.12 (12)	C7—C8—C9	117.5 (2)
O1—S1—N1	106.90 (10)	C7—C8—C13	122.8 (2)
O2—S1—C1	107.66 (12)	C9—C8—C13	119.7 (2)
O1—S1—C1	107.05 (11)	C10—C9—C8	120.8 (3)
N1—S1—C1	108.29 (11)	C10—C9—H9	119.6
C7—N1—S1	121.78 (16)	C8—C9—H9	119.6
C7—N1—H1N	113.2 (19)	C11—C10—C9	120.7 (3)
S1—N1—H1N	115.5 (19)	C11—C10—H10	119.7
C2—C1—C6	120.6 (2)	C9—C10—H10	119.7
C2—C1—S1	120.11 (19)	C10—C11—C12	121.4 (3)
C6—C1—S1	119.31 (19)	C10—C11—H11	119.3
C3—C2—C1	119.3 (3)	C12—C11—H11	119.3
C3—C2—H2	120.4	C11—C12—C7	117.7 (2)
C1—C2—H2	120.4	C11—C12—C14	119.1 (2)
C4—C3—C2	119.8 (3)	C7—C12—C14	123.1 (2)
C4—C3—H3	120.1	C8—C13—H13A	109.5
C2—C3—H3	120.1	C8—C13—H13B	109.5
C3—C4—C5	121.3 (3)	H13A—C13—H13B	109.5
C3—C4—Cl1	119.4 (2)	C8—C13—H13C	109.5
C5—C4—Cl1	119.3 (2)	H13A—C13—H13C	109.5
C6—C5—C4	119.4 (3)	H13B—C13—H13C	109.5
C6—C5—H5	120.3	C12—C14—H14A	109.5
C4—C5—H5	120.3	C12—C14—H14B	109.5
C5—C6—C1	119.6 (2)	H14A—C14—H14B	109.5
C5—C6—H6	120.2	C12—C14—H14C	109.5
C1—C6—H6	120.2	H14A—C14—H14C	109.5
C8—C7—C12	121.8 (2)	H14B—C14—H14C	109.5
C8—C7—N1	120.0 (2)
O2—S1—N1—C7	174.71 (18)	S1—C1—C6—C5	−175.2 (2)
O1—S1—N1—C7	45.1 (2)	S1—N1—C7—C8	97.6 (2)
C1—S1—N1—C7	−69.9 (2)	S1—N1—C7—C12	−83.4 (3)
O2—S1—C1—C2	9.0 (2)	C12—C7—C8—C9	3.2 (4)
O1—S1—C1—C2	139.75 (19)	N1—C7—C8—C9	−177.8 (2)
N1—S1—C1—C2	−105.3 (2)	C12—C7—C8—C13	−175.3 (2)
O2—S1—C1—C6	−172.5 (2)	N1—C7—C8—C13	3.7 (4)
O1—S1—C1—C6	−41.8 (2)	C7—C8—C9—C10	−1.1 (4)
N1—S1—C1—C6	73.1 (2)	C13—C8—C9—C10	177.4 (2)
C6—C1—C2—C3	−2.8 (4)	C8—C9—C10—C11	−1.2 (4)
S1—C1—C2—C3	175.7 (2)	C9—C10—C11—C12	1.5 (4)
C1—C2—C3—C4	0.2 (4)	C10—C11—C12—C7	0.5 (4)
C2—C3—C4—C5	2.0 (4)	C10—C11—C12—C14	−178.4 (3)
C2—C3—C4—Cl1	−177.7 (2)	C8—C7—C12—C11	−2.9 (4)
C3—C4—C5—C6	−1.5 (4)	N1—C7—C12—C11	178.1 (2)
Cl1—C4—C5—C6	178.1 (2)	C8—C7—C12—C14	175.9 (2)
C4—C5—C6—C1	−1.1 (4)	N1—C7—C12—C14	−3.1 (4)
C2—C1—C6—C5	3.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.28 (2)	3.083 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.28 (2)	3.083 (3)	166 (3)

Symmetry code: (i) .