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

In the title compound, C(15)H(17)NO(2)S, the mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 71.6 (1)°. The two benzene rings are tilted by 47.0 (1)° relative to each other. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008 ▶; 2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Triclinic,

a = 8.1789 (8) Å

b = 8.2659 (9) Å

c = 11.005 (1) Å

α = 96.249 (9)°

β = 96.078 (9)°

γ = 106.782 (9)°

V = 700.68 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 299 K

0.48 × 0.26 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.898, T max = 0.973

4894 measured reflections

2862 independent reflections

2446 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.05

2862 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.24 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/S1600536809049563/ci2971sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049563/ci2971Isup2.hkl

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

C15H17NO2S	Z = 2
Mr = 275.36	F(000) = 292
Triclinic, P1	Dx = 1.305 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1789 (8) Å	Cell parameters from 2978 reflections
b = 8.2659 (9) Å	θ = 3.0–27.9°
c = 11.005 (1) Å	µ = 0.23 mm−1
α = 96.249 (9)°	T = 299 K
β = 96.078 (9)°	Prism, colourless
γ = 106.782 (9)°	0.48 × 0.26 × 0.12 mm
V = 700.68 (12) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2862 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
graphite	Rint = 0.010
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 = −10→10
Tmin = 0.898, Tmax = 0.973	k = −10→7
4894 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.064P)2 + 0.2128P] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.24 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	0.1125 (2)	0.5794 (2)	0.78239 (16)	0.0390 (4)
C2	0.2116 (2)	0.6728 (2)	0.89249 (16)	0.0440 (4)
C3	0.1243 (3)	0.7397 (3)	0.97740 (17)	0.0496 (4)
H3	0.1876	0.8030	1.0513	0.060*
C4	−0.0514 (3)	0.7168 (2)	0.95762 (18)	0.0480 (4)
C5	−0.1451 (2)	0.6234 (3)	0.84761 (18)	0.0505 (4)
H5	−0.2633	0.6063	0.8322	0.061*
C6	−0.0645 (2)	0.5551 (2)	0.76046 (17)	0.0458 (4)
H6	−0.1287	0.4925	0.6866	0.055*
C7	0.4102 (2)	0.7886 (2)	0.61387 (14)	0.0380 (4)
C8	0.3900 (2)	0.9481 (2)	0.64940 (15)	0.0432 (4)
C9	0.5397 (3)	1.0860 (3)	0.68291 (19)	0.0599 (5)
H9	0.5304	1.1944	0.7053	0.072*
C10	0.7000 (3)	1.0659 (3)	0.6837 (2)	0.0693 (7)
H10	0.7978	1.1600	0.7075	0.083*
C11	0.7175 (3)	0.9075 (3)	0.6495 (2)	0.0691 (7)
H11	0.8268	0.8942	0.6511	0.083*
C12	0.5722 (2)	0.7676 (3)	0.61251 (19)	0.0525 (5)
H12	0.5831	0.6607	0.5870	0.063*
C13	0.4036 (3)	0.7076 (3)	0.9262 (2)	0.0642 (6)
H13A	0.4627	0.7664	0.8654	0.077*
H13B	0.4287	0.6014	0.9290	0.077*
H13C	0.4416	0.7771	1.0057	0.077*
C14	−0.1363 (3)	0.7946 (3)	1.0542 (2)	0.0660 (6)
H14A	−0.0497	0.8623	1.1206	0.079*
H14B	−0.2169	0.7053	1.0855	0.079*
H14C	−0.1960	0.8657	1.0176	0.079*
C15	0.2154 (3)	0.9733 (2)	0.6503 (2)	0.0583 (5)
H15A	0.1600	0.9167	0.7135	0.070*
H15B	0.1462	0.9261	0.5714	0.070*
H15C	0.2283	1.0932	0.6667	0.070*
N1	0.26247 (19)	0.64126 (19)	0.57272 (13)	0.0409 (3)
H1N	0.175 (2)	0.659 (3)	0.5378 (18)	0.049*
O1	0.06289 (17)	0.36111 (16)	0.58290 (13)	0.0527 (3)
O2	0.35102 (17)	0.45144 (17)	0.70879 (13)	0.0524 (3)
S1	0.20156 (5)	0.49271 (5)	0.65960 (4)	0.04048 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0394 (9)	0.0368 (8)	0.0420 (9)	0.0129 (7)	0.0056 (7)	0.0065 (7)
C2	0.0413 (9)	0.0472 (9)	0.0434 (9)	0.0139 (8)	0.0035 (7)	0.0074 (7)
C3	0.0527 (11)	0.0531 (11)	0.0422 (9)	0.0177 (9)	0.0034 (8)	0.0025 (8)
C4	0.0538 (11)	0.0481 (10)	0.0500 (10)	0.0232 (9)	0.0146 (8)	0.0127 (8)
C5	0.0404 (9)	0.0584 (11)	0.0571 (11)	0.0200 (9)	0.0087 (8)	0.0123 (9)
C6	0.0412 (9)	0.0480 (10)	0.0473 (10)	0.0143 (8)	0.0020 (7)	0.0051 (8)
C7	0.0374 (8)	0.0422 (9)	0.0328 (8)	0.0095 (7)	0.0055 (6)	0.0050 (6)
C8	0.0522 (10)	0.0408 (9)	0.0344 (8)	0.0100 (8)	0.0084 (7)	0.0046 (7)
C9	0.0737 (14)	0.0435 (10)	0.0498 (11)	0.0012 (10)	0.0025 (10)	0.0043 (8)
C10	0.0565 (13)	0.0683 (14)	0.0624 (13)	−0.0109 (11)	−0.0078 (10)	0.0199 (11)
C11	0.0368 (10)	0.0928 (18)	0.0765 (15)	0.0099 (11)	0.0044 (10)	0.0380 (13)
C12	0.0426 (10)	0.0627 (12)	0.0579 (11)	0.0201 (9)	0.0117 (8)	0.0176 (9)
C13	0.0440 (11)	0.0873 (16)	0.0544 (12)	0.0194 (11)	−0.0049 (9)	−0.0059 (11)
C14	0.0683 (14)	0.0747 (15)	0.0644 (13)	0.0333 (12)	0.0219 (11)	0.0065 (11)
C15	0.0692 (13)	0.0461 (11)	0.0683 (13)	0.0261 (10)	0.0246 (11)	0.0074 (9)
N1	0.0391 (8)	0.0405 (8)	0.0409 (8)	0.0117 (6)	0.0020 (6)	0.0006 (6)
O1	0.0516 (7)	0.0371 (6)	0.0622 (8)	0.0085 (6)	0.0031 (6)	−0.0050 (6)
O2	0.0499 (7)	0.0472 (7)	0.0660 (8)	0.0246 (6)	0.0075 (6)	0.0078 (6)
S1	0.0399 (2)	0.0329 (2)	0.0477 (3)	0.01217 (17)	0.00452 (18)	0.00091 (17)

C1—C6	1.394 (2)	C10—C11	1.375 (4)
C1—C2	1.396 (2)	C10—H10	0.93
C1—S1	1.7799 (17)	C11—C12	1.384 (3)
C2—C3	1.394 (3)	C11—H11	0.93
C2—C13	1.510 (2)	C12—H12	0.93
C3—C4	1.385 (3)	C13—H13A	0.96
C3—H3	0.93	C13—H13B	0.96
C4—C5	1.381 (3)	C13—H13C	0.96
C4—C14	1.513 (3)	C14—H14A	0.96
C5—C6	1.380 (3)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—C12	1.386 (2)	C15—H15B	0.96
C7—C8	1.395 (2)	C15—H15C	0.96
C7—N1	1.436 (2)	N1—S1	1.6350 (16)
C8—C9	1.393 (3)	N1—H1N	0.832 (15)
C8—C15	1.503 (3)	O1—S1	1.4377 (13)
C9—C10	1.368 (3)	O2—S1	1.4299 (13)
C9—H9	0.93
C6—C1—C2	120.83 (16)	C12—C11—H11	120.1
C6—C1—S1	115.77 (13)	C11—C12—C7	119.3 (2)
C2—C1—S1	123.34 (13)	C11—C12—H12	120.3
C3—C2—C1	116.59 (16)	C7—C12—H12	120.3
C3—C2—C13	117.89 (17)	C2—C13—H13A	109.5
C1—C2—C13	125.51 (17)	C2—C13—H13B	109.5
C4—C3—C2	123.53 (18)	H13A—C13—H13B	109.5
C4—C3—H3	118.2	C2—C13—H13C	109.5
C2—C3—H3	118.2	H13A—C13—H13C	109.5
C5—C4—C3	118.18 (17)	H13B—C13—H13C	109.5
C5—C4—C14	121.52 (18)	C4—C14—H14A	109.5
C3—C4—C14	120.30 (19)	C4—C14—H14B	109.5
C6—C5—C4	120.45 (17)	H14A—C14—H14B	109.5
C6—C5—H5	119.8	C4—C14—H14C	109.5
C4—C5—H5	119.8	H14A—C14—H14C	109.5
C5—C6—C1	120.42 (17)	H14B—C14—H14C	109.5
C5—C6—H6	119.8	C8—C15—H15A	109.5
C1—C6—H6	119.8	C8—C15—H15B	109.5
C12—C7—C8	121.51 (17)	H15A—C15—H15B	109.5
C12—C7—N1	117.73 (16)	C8—C15—H15C	109.5
C8—C7—N1	120.71 (15)	H15A—C15—H15C	109.5
C9—C8—C7	117.21 (18)	H15B—C15—H15C	109.5
C9—C8—C15	120.60 (18)	C7—N1—S1	121.46 (11)
C7—C8—C15	122.19 (16)	C7—N1—H1N	116.5 (14)
C10—C9—C8	121.6 (2)	S1—N1—H1N	108.7 (15)
C10—C9—H9	119.2	O2—S1—O1	118.89 (8)
C8—C9—H9	119.2	O2—S1—N1	108.05 (8)
C9—C10—C11	120.4 (2)	O1—S1—N1	104.94 (8)
C9—C10—H10	119.8	O2—S1—C1	109.57 (8)
C11—C10—H10	119.8	O1—S1—C1	107.40 (8)
C10—C11—C12	119.9 (2)	N1—S1—C1	107.42 (8)
C10—C11—H11	120.1
C6—C1—C2—C3	−0.2 (3)	C15—C8—C9—C10	179.47 (19)
S1—C1—C2—C3	176.86 (13)	C8—C9—C10—C11	0.9 (3)
C6—C1—C2—C13	−179.88 (19)	C9—C10—C11—C12	0.8 (4)
S1—C1—C2—C13	−2.8 (3)	C10—C11—C12—C7	−1.8 (3)
C1—C2—C3—C4	0.4 (3)	C8—C7—C12—C11	1.2 (3)
C13—C2—C3—C4	−179.95 (19)	N1—C7—C12—C11	178.85 (17)
C2—C3—C4—C5	−0.3 (3)	C12—C7—N1—S1	75.97 (18)
C2—C3—C4—C14	−179.61 (19)	C8—C7—N1—S1	−106.39 (17)
C3—C4—C5—C6	0.0 (3)	C7—N1—S1—O2	−46.56 (15)
C14—C4—C5—C6	179.35 (18)	C7—N1—S1—O1	−174.35 (12)
C4—C5—C6—C1	0.1 (3)	C7—N1—S1—C1	71.57 (14)
C2—C1—C6—C5	0.0 (3)	C6—C1—S1—O2	−152.26 (13)
S1—C1—C6—C5	−177.30 (14)	C2—C1—S1—O2	30.51 (17)
C12—C7—C8—C9	0.3 (3)	C6—C1—S1—O1	−21.81 (16)
N1—C7—C8—C9	−177.20 (15)	C2—C1—S1—O1	160.95 (14)
C12—C7—C8—C15	179.46 (17)	C6—C1—S1—N1	90.60 (14)
N1—C7—C8—C15	1.9 (3)	C2—C1—S1—N1	−86.63 (16)
C7—C8—C9—C10	−1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.19 (2)	3.002 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.19 (2)	3.002 (2)	165 (2)

Symmetry code: (i) .