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

In the crystal structure of the title compound, C(14)H(14)ClNO(2)S, the two aromatic rings are tilted relative to each other by 45.8 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Triclinic,

a = 8.1200 (8) Å

b = 8.1832 (8) Å

c = 10.985 (1) Å

α = 95.81 (1)°

β = 96.92 (1)°

γ = 106.82 (1)°

V = 686.46 (11) Å3

Z = 2

Cu Kα radiation

μ = 3.86 mm−1

T = 299 K

0.50 × 0.48 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.228, T max = 0.500

2572 measured reflections

2366 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.054

3 standard reflections frequency: 120 min intensity decay: 2.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.235

S = 1.10

2366 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.82 e Å−3

Δρmin = −0.63 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536809009623/bt2900sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009623/bt2900Isup2.hkl

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

C14H14ClNO2S	Z = 2
Mr = 295.77	F(000) = 308
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.1200 (8) Å	Cell parameters from 25 reflections
b = 8.1832 (8) Å	θ = 5.7–25.2°
c = 10.985 (1) Å	µ = 3.86 mm−1
α = 95.81 (1)°	T = 299 K
β = 96.92 (1)°	Prism, colourless
γ = 106.82 (1)°	0.50 × 0.48 × 0.18 mm
V = 686.46 (11) Å3

Enraf–Nonius CAD-4 diffractometer	2194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 66.9°, θmin = 4.1°
ω/2θ scans	h = −9→1
Absorption correction: psi-scan (North et al., 1968)	k = −9→9
Tmin = 0.228, Tmax = 0.500	l = −13→13
2572 measured reflections	3 standard reflections every 120 min
2366 independent reflections	intensity decay: 2.5%

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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.235	w = 1/[σ2(Fo2) + (0.1867P)2 + 0.2192P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.003
2366 reflections	Δρmax = 0.82 e Å−3
178 parameters	Δρmin = −0.63 e Å−3
0 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: 0.020 (4)

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	0.35649 (13)	0.29943 (14)	0.56281 (9)	0.0698 (5)
S1	0.70711 (9)	−0.00610 (8)	0.15793 (6)	0.0388 (4)
O1	0.8587 (3)	−0.0468 (3)	0.2078 (2)	0.0511 (6)
O2	0.5669 (3)	−0.1383 (3)	0.0812 (2)	0.0518 (7)
N1	0.7667 (3)	0.1454 (3)	0.0718 (2)	0.0408 (6)
H1N	0.678 (5)	0.160 (5)	0.026 (3)	0.049*
C1	0.6176 (4)	0.0795 (4)	0.2802 (3)	0.0381 (7)
C2	0.7184 (4)	0.1738 (4)	0.3914 (3)	0.0446 (8)
C3	0.6322 (5)	0.2414 (4)	0.4757 (3)	0.0492 (8)
H3	0.6954	0.3075	0.5496	0.059*
C4	0.4541 (5)	0.2123 (4)	0.4518 (3)	0.0471 (8)
C5	0.3557 (4)	0.1194 (4)	0.3436 (3)	0.0483 (8)
H5	0.2361	0.1015	0.3284	0.058*
C6	0.4388 (4)	0.0529 (4)	0.2572 (3)	0.0445 (7)
H6	0.3743	−0.0105	0.1828	0.053*
C7	0.9159 (4)	0.2918 (4)	0.1137 (2)	0.0370 (7)
C8	0.8982 (4)	0.4545 (4)	0.1516 (3)	0.0417 (7)
C9	1.0502 (6)	0.5921 (4)	0.1866 (3)	0.0580 (9)
H9	1.0420	0.7016	0.2100	0.070*
C10	1.2117 (6)	0.5710 (5)	0.1876 (4)	0.0654 (11)
H10	1.3113	0.6648	0.2132	0.078*
C11	1.2262 (5)	0.4090 (6)	0.1501 (4)	0.0655 (11)
H11	1.3357	0.3943	0.1511	0.079*
C12	1.0791 (5)	0.2706 (5)	0.1118 (3)	0.0516 (8)
H12	1.0889	0.1629	0.0846	0.062*
C13	0.9139 (5)	0.2097 (6)	0.4271 (3)	0.0607 (10)
H13A	0.9401	0.1025	0.4258	0.073*
H13B	0.9513	0.2741	0.5088	0.073*
H13C	0.9736	0.2753	0.3691	0.073*
C14	0.7233 (5)	0.4810 (4)	0.1522 (4)	0.0570 (10)
H14A	0.6460	0.4174	0.0787	0.068*
H14B	0.7352	0.6015	0.1546	0.068*
H14C	0.6767	0.4410	0.2239	0.068*

	U11	U22	U33	U12	U13	U23
Cl1	0.0723 (8)	0.0846 (8)	0.0629 (7)	0.0384 (6)	0.0258 (5)	−0.0018 (5)
S1	0.0430 (6)	0.0280 (5)	0.0466 (5)	0.0131 (3)	0.0107 (3)	−0.0002 (3)
O1	0.0554 (14)	0.0426 (12)	0.0650 (14)	0.0270 (10)	0.0156 (11)	0.0088 (10)
O2	0.0570 (15)	0.0327 (11)	0.0614 (14)	0.0106 (10)	0.0117 (11)	−0.0058 (9)
N1	0.0440 (15)	0.0362 (13)	0.0422 (13)	0.0137 (11)	0.0079 (10)	−0.0001 (10)
C1	0.0431 (17)	0.0308 (14)	0.0427 (15)	0.0129 (11)	0.0114 (12)	0.0052 (11)
C2	0.0422 (18)	0.0510 (17)	0.0449 (16)	0.0191 (13)	0.0091 (13)	0.0103 (13)
C3	0.052 (2)	0.0490 (18)	0.0446 (16)	0.0155 (14)	0.0073 (14)	−0.0003 (13)
C4	0.053 (2)	0.0497 (18)	0.0484 (17)	0.0255 (15)	0.0195 (14)	0.0119 (14)
C5	0.0429 (18)	0.0519 (18)	0.0543 (18)	0.0202 (14)	0.0119 (14)	0.0052 (14)
C6	0.0441 (18)	0.0426 (16)	0.0473 (16)	0.0147 (13)	0.0081 (13)	0.0037 (12)
C7	0.0427 (16)	0.0365 (14)	0.0328 (13)	0.0119 (12)	0.0113 (11)	0.0043 (10)
C8	0.058 (2)	0.0339 (14)	0.0338 (14)	0.0128 (13)	0.0117 (12)	0.0031 (11)
C9	0.075 (3)	0.0388 (17)	0.0516 (18)	0.0032 (15)	0.0113 (16)	0.0070 (13)
C10	0.059 (2)	0.058 (2)	0.062 (2)	−0.0077 (17)	0.0005 (17)	0.0193 (17)
C11	0.041 (2)	0.082 (3)	0.073 (2)	0.0107 (18)	0.0111 (16)	0.032 (2)
C12	0.049 (2)	0.0553 (19)	0.0581 (19)	0.0217 (15)	0.0186 (15)	0.0146 (15)
C13	0.043 (2)	0.080 (3)	0.0544 (19)	0.0199 (17)	−0.0005 (15)	−0.0072 (17)
C14	0.074 (2)	0.0400 (17)	0.069 (2)	0.0274 (17)	0.0329 (19)	0.0081 (15)

Cl1—C4	1.734 (3)	C7—C12	1.388 (5)
S1—O1	1.427 (2)	C7—C8	1.407 (4)
S1—O2	1.431 (2)	C8—C9	1.390 (5)
S1—N1	1.633 (3)	C8—C14	1.498 (5)
S1—C1	1.778 (3)	C9—C10	1.370 (6)
N1—C7	1.424 (4)	C9—H9	0.9300
N1—H1N	0.87 (4)	C10—C11	1.391 (7)
C1—C6	1.392 (5)	C10—H10	0.9300
C1—C2	1.400 (4)	C11—C12	1.373 (5)
C2—C3	1.389 (5)	C11—H11	0.9300
C2—C13	1.522 (5)	C12—H12	0.9300
C3—C4	1.383 (5)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.366 (5)	C13—H13C	0.9600
C5—C6	1.383 (5)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O1—S1—O2	119.17 (14)	C8—C7—N1	121.0 (3)
O1—S1—N1	108.06 (14)	C9—C8—C7	117.4 (3)
O2—S1—N1	105.21 (14)	C9—C8—C14	120.8 (3)
O1—S1—C1	109.71 (14)	C7—C8—C14	121.9 (3)
O2—S1—C1	106.93 (14)	C10—C9—C8	121.9 (3)
N1—S1—C1	107.12 (13)	C10—C9—H9	119.1
C7—N1—S1	121.1 (2)	C8—C9—H9	119.1
C7—N1—H1N	118 (2)	C9—C10—C11	119.8 (3)
S1—N1—H1N	112 (3)	C9—C10—H10	120.1
C6—C1—C2	121.0 (3)	C11—C10—H10	120.1
C6—C1—S1	115.7 (2)	C12—C11—C10	120.1 (4)
C2—C1—S1	123.3 (2)	C12—C11—H11	119.9
C3—C2—C1	116.9 (3)	C10—C11—H11	119.9
C3—C2—C13	117.4 (3)	C11—C12—C7	119.8 (3)
C1—C2—C13	125.6 (3)	C11—C12—H12	120.1
C4—C3—C2	121.3 (3)	C7—C12—H12	120.1
C4—C3—H3	119.4	C2—C13—H13A	109.5
C2—C3—H3	119.4	C2—C13—H13B	109.5
C5—C4—C3	121.7 (3)	H13A—C13—H13B	109.5
C5—C4—Cl1	120.0 (3)	C2—C13—H13C	109.5
C3—C4—Cl1	118.3 (3)	H13A—C13—H13C	109.5
C4—C5—C6	118.1 (3)	H13B—C13—H13C	109.5
C4—C5—H5	120.9	C8—C14—H14A	109.5
C6—C5—H5	120.9	C8—C14—H14B	109.5
C5—C6—C1	120.9 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.6	C8—C14—H14C	109.5
C1—C6—H6	119.6	H14A—C14—H14C	109.5
C12—C7—C8	121.0 (3)	H14B—C14—H14C	109.5
C12—C7—N1	118.0 (3)
O1—S1—N1—C7	−45.5 (2)	Cl1—C4—C5—C6	179.7 (2)
O2—S1—N1—C7	−173.8 (2)	C4—C5—C6—C1	0.2 (5)
C1—S1—N1—C7	72.7 (2)	C2—C1—C6—C5	0.2 (5)
O1—S1—C1—C6	−152.0 (2)	S1—C1—C6—C5	−177.4 (2)
O2—S1—C1—C6	−21.4 (3)	S1—N1—C7—C12	75.9 (3)
N1—S1—C1—C6	90.9 (2)	S1—N1—C7—C8	−106.4 (3)
O1—S1—C1—C2	30.4 (3)	C12—C7—C8—C9	0.1 (4)
O2—S1—C1—C2	161.0 (3)	N1—C7—C8—C9	−177.5 (3)
N1—S1—C1—C2	−86.6 (3)	C12—C7—C8—C14	178.9 (3)
C6—C1—C2—C3	−1.1 (5)	N1—C7—C8—C14	1.3 (4)
S1—C1—C2—C3	176.3 (2)	C7—C8—C9—C10	−1.6 (5)
C6—C1—C2—C13	179.4 (3)	C14—C8—C9—C10	179.5 (3)
S1—C1—C2—C13	−3.1 (5)	C8—C9—C10—C11	1.5 (6)
C1—C2—C3—C4	1.8 (5)	C9—C10—C11—C12	0.3 (6)
C13—C2—C3—C4	−178.7 (3)	C10—C11—C12—C7	−1.8 (5)
C2—C3—C4—C5	−1.5 (5)	C8—C7—C12—C11	1.6 (5)
C2—C3—C4—Cl1	179.3 (2)	N1—C7—C12—C11	179.3 (3)
C3—C4—C5—C6	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.87 (4)	2.14 (4)	2.993 (4)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.87 (4)	2.14 (4)	2.993 (4)	167 (3)

Symmetry code: (i) .