N-(3,4-Dimethyl-phen-yl)benzene-sulfonamide.

The structure of the title compound, C(14)H(15)NO(2)S, shows the sulfonamide N atom to be approximately perpendicular to the plane through the S-bound benzene ring [the N-S-C-C torsion angle is -87.4 (3)°] and to lie to the opposide side of this ring to the two sulfonamide O atoms. The N-bound benzene ring is splayed out with respect to the rest of the mol-ecule so that overall, the mol-ecule adopts a twisted conformation. The dihedral angle between the two benzene rings is 64.5 (3)°. In the crystal, supra-molecular chains aligned along the b axis are formed via N-H⋯O hydrogen bonds.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For the structure of the S-tosyl derivative, see: Gowda et al. (2009 ▶). For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.33

Monoclinic,

a = 24.2129 (12) Å

b = 9.2616 (5) Å

c = 16.5584 (16) Å

β = 132.014 (2)°

V = 2758.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.31 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.947

11486 measured reflections

2864 independent reflections

2112 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.196

S = 1.09

2864 reflections

168 parameters

37 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026656/hb5533sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026656/hb5533Isup2.hkl

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

C14H15NO2S	F(000) = 1104
Mr = 261.33	Dx = 1.258 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2975 reflections
a = 24.2129 (12) Å	θ = 2.5–24.2°
b = 9.2616 (5) Å	µ = 0.23 mm−1
c = 16.5584 (16) Å	T = 293 K
β = 132.014 (2)°	Prism, colourless
V = 2758.9 (3) Å3	0.31 × 0.08 × 0.07 mm
Z = 8

Bruker APEXII CCD diffractometer	2864 independent reflections
Radiation source: fine-focus sealed tube	2112 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→30
Tmin = 0.795, Tmax = 0.947	k = −11→11
11486 measured reflections	l = −20→20

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.1221P)2 + 0.6451P] where P = (Fo2 + 2Fc2)/3
2864 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.56 e Å−3
37 restraints	Δρmin = −0.65 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.21969 (4)	0.08206 (8)	0.26474 (6)	0.0437 (3)
O1	0.16507 (13)	0.0323 (3)	0.15598 (16)	0.0610 (6)
O2	0.22892 (12)	0.2337 (2)	0.28664 (18)	0.0567 (6)
N1	0.29812 (14)	0.0196 (3)	0.3083 (2)	0.0492 (6)
H1n	0.291 (2)	−0.063 (2)	0.280 (3)	0.059*
C1	0.20212 (16)	0.0052 (3)	0.3427 (2)	0.0448 (7)
C2	0.2297 (2)	0.0696 (4)	0.4375 (3)	0.0690 (10)
H2	0.2586	0.1526	0.4613	0.083*
C3	0.2149 (3)	0.0117 (5)	0.4979 (3)	0.0875 (13)
H3	0.2337	0.0557	0.5625	0.105*
C4	0.1730 (3)	−0.1089 (5)	0.4635 (4)	0.0935 (14)
H4	0.1643	−0.1497	0.5054	0.112*
C5	0.1437 (4)	−0.1704 (6)	0.3671 (5)	0.1114 (18)
H5	0.1129	−0.2507	0.3418	0.134*
C6	0.1591 (3)	−0.1147 (5)	0.3065 (4)	0.0851 (13)
H6	0.1403	−0.1588	0.2420	0.102*
C7	0.36691 (17)	0.0393 (3)	0.4183 (2)	0.0470 (7)
C8	0.39442 (19)	0.1756 (3)	0.4603 (3)	0.0537 (8)
H8	0.3673	0.2562	0.4178	0.064*
C9	0.46209 (19)	0.1938 (4)	0.5652 (3)	0.0607 (9)
C10	0.50388 (19)	0.0737 (4)	0.6287 (3)	0.0638 (10)
C11	0.4750 (2)	−0.0623 (4)	0.5834 (3)	0.0683 (10)
H11	0.5022	−0.1436	0.6246	0.082*
C12	0.4080 (2)	−0.0805 (4)	0.4804 (3)	0.0581 (8)
H12	0.3902	−0.1728	0.4523	0.070*
C13	0.4905 (3)	0.3462 (5)	0.6065 (4)	0.1030 (16)
H13A	0.5075	0.3559	0.6778	0.154*
H13B	0.4511	0.4139	0.5581	0.154*
H13C	0.5309	0.3653	0.6096	0.154*
C14	0.5778 (2)	0.0900 (6)	0.7430 (3)	0.0921 (15)
H14A	0.6053	0.1672	0.7454	0.138*
H14B	0.6054	0.0017	0.7654	0.138*
H14C	0.5697	0.1115	0.7912	0.138*

	U11	U22	U33	U12	U13	U23
S1	0.0524 (5)	0.0421 (5)	0.0424 (4)	0.0023 (3)	0.0340 (4)	0.0028 (3)
O1	0.0623 (14)	0.0769 (16)	0.0388 (12)	−0.0017 (12)	0.0317 (11)	−0.0011 (10)
O2	0.0678 (14)	0.0410 (12)	0.0680 (14)	0.0076 (10)	0.0483 (13)	0.0091 (10)
N1	0.0572 (15)	0.0462 (14)	0.0533 (15)	−0.0004 (12)	0.0407 (13)	−0.0075 (12)
C1	0.0560 (16)	0.0416 (15)	0.0466 (15)	−0.0004 (12)	0.0384 (14)	−0.0012 (12)
C2	0.089 (2)	0.072 (2)	0.0622 (19)	−0.0237 (18)	0.0574 (19)	−0.0184 (16)
C3	0.118 (3)	0.102 (3)	0.071 (2)	−0.024 (2)	0.075 (2)	−0.019 (2)
C4	0.132 (3)	0.098 (3)	0.091 (3)	−0.025 (3)	0.092 (3)	−0.005 (2)
C5	0.155 (4)	0.101 (3)	0.118 (3)	−0.054 (3)	0.108 (3)	−0.021 (2)
C6	0.121 (3)	0.079 (2)	0.084 (2)	−0.038 (2)	0.080 (2)	−0.026 (2)
C7	0.0513 (16)	0.0521 (17)	0.0538 (17)	0.0004 (13)	0.0418 (15)	0.0004 (14)
C8	0.0551 (18)	0.0536 (19)	0.0588 (19)	0.0010 (14)	0.0408 (17)	−0.0001 (14)
C9	0.0553 (19)	0.071 (2)	0.064 (2)	−0.0095 (17)	0.0436 (18)	−0.0090 (18)
C10	0.0481 (19)	0.094 (3)	0.058 (2)	−0.0018 (18)	0.0389 (17)	0.0061 (19)
C11	0.062 (2)	0.075 (3)	0.074 (2)	0.0142 (18)	0.048 (2)	0.0238 (19)
C12	0.061 (2)	0.0554 (19)	0.067 (2)	0.0035 (15)	0.0462 (18)	0.0068 (16)
C13	0.078 (3)	0.098 (4)	0.091 (3)	−0.020 (3)	0.039 (3)	−0.022 (3)
C14	0.058 (2)	0.142 (4)	0.068 (3)	−0.008 (2)	0.038 (2)	0.011 (3)

S1—O1	1.420 (2)	C7—C8	1.379 (4)
S1—O2	1.430 (2)	C7—C12	1.381 (4)
S1—N1	1.621 (3)	C8—C9	1.386 (5)
S1—C1	1.758 (3)	C8—H8	0.9300
N1—C7	1.436 (4)	C9—C10	1.394 (5)
N1—H1n	0.85 (3)	C9—C13	1.518 (6)
C1—C6	1.356 (5)	C10—C11	1.392 (5)
C1—C2	1.364 (4)	C10—C14	1.508 (5)
C2—C3	1.379 (5)	C11—C12	1.365 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.351 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.363 (6)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.384 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O1—S1—O2	119.67 (15)	C12—C7—N1	119.2 (3)
O1—S1—N1	105.54 (14)	C7—C8—C9	120.7 (3)
O2—S1—N1	107.46 (13)	C7—C8—H8	119.7
O1—S1—C1	108.80 (14)	C9—C8—H8	119.7
O2—S1—C1	106.57 (13)	C8—C9—C10	120.1 (3)
N1—S1—C1	108.39 (14)	C8—C9—C13	118.5 (4)
C7—N1—S1	122.54 (19)	C10—C9—C13	121.4 (4)
C7—N1—H1N	117 (2)	C11—C10—C9	117.8 (3)
S1—N1—H1N	109 (2)	C11—C10—C14	120.9 (4)
C6—C1—C2	120.5 (3)	C9—C10—C14	121.3 (4)
C6—C1—S1	119.9 (2)	C12—C11—C10	122.2 (3)
C2—C1—S1	119.6 (2)	C12—C11—H11	118.9
C1—C2—C3	120.0 (4)	C10—C11—H11	118.9
C1—C2—H2	120.0	C11—C12—C7	119.5 (3)
C3—C2—H2	120.0	C11—C12—H12	120.2
C4—C3—C2	120.1 (4)	C7—C12—H12	120.2
C4—C3—H3	120.0	C9—C13—H13A	109.5
C2—C3—H3	120.0	C9—C13—H13B	109.5
C3—C4—C5	119.7 (4)	H13A—C13—H13B	109.5
C3—C4—H4	120.1	C9—C13—H13C	109.5
C5—C4—H4	120.1	H13A—C13—H13C	109.5
C4—C5—C6	120.7 (4)	H13B—C13—H13C	109.5
C4—C5—H5	119.7	C10—C14—H14A	109.5
C6—C5—H5	119.7	C10—C14—H14B	109.5
C1—C6—C5	119.0 (4)	H14A—C14—H14B	109.5
C1—C6—H6	120.5	C10—C14—H14C	109.5
C5—C6—H6	120.5	H14A—C14—H14C	109.5
C8—C7—C12	119.7 (3)	H14B—C14—H14C	109.5
C8—C7—N1	121.0 (3)
O1—S1—N1—C7	−176.1 (2)	C4—C5—C6—C1	−2.1 (9)
O2—S1—N1—C7	55.1 (3)	S1—N1—C7—C8	−60.8 (4)
C1—S1—N1—C7	−59.7 (3)	S1—N1—C7—C12	123.0 (3)
O1—S1—C1—C6	19.3 (4)	C12—C7—C8—C9	−1.6 (4)
O2—S1—C1—C6	149.6 (3)	N1—C7—C8—C9	−177.7 (3)
N1—S1—C1—C6	−95.0 (4)	C7—C8—C9—C10	1.4 (5)
O1—S1—C1—C2	−158.3 (3)	C7—C8—C9—C13	178.7 (3)
O2—S1—C1—C2	−28.0 (3)	C8—C9—C10—C11	−0.5 (5)
N1—S1—C1—C2	87.4 (3)	C13—C9—C10—C11	−177.8 (4)
C6—C1—C2—C3	0.9 (6)	C8—C9—C10—C14	179.9 (3)
S1—C1—C2—C3	178.6 (3)	C13—C9—C10—C14	2.6 (5)
C1—C2—C3—C4	0.1 (7)	C9—C10—C11—C12	−0.2 (5)
C2—C3—C4—C5	−2.1 (9)	C14—C10—C11—C12	179.4 (3)
C3—C4—C5—C6	3.1 (10)	C10—C11—C12—C7	−0.1 (5)
C2—C1—C6—C5	0.1 (7)	C8—C7—C12—C11	0.9 (5)
S1—C1—C6—C5	−177.6 (4)	N1—C7—C12—C11	177.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O2i	0.85 (3)	2.07 (2)	2.921 (3)	177 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O2i	0.85 (3)	2.07 (2)	2.921 (3)	177 (5)

Symmetry code: (i) .