N-(3,5-Dimethyl-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(15)H(17)NO(2)S, the dihedral angle between the two aromatic rings is 53.9 (1)°. The crystal structure features inversion-related dimers linked by N-H⋯O hydrogen bonds.

Related literature

For preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study of the effects of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2010 ▶); Nirmala et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Triclinic,

a = 8.311 (1) Å

b = 8.521 (1) Å

c = 11.412 (1) Å

α = 99.86 (1)°

β = 97.62 (1)°

γ = 108.14 (1)°

V = 741.60 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.45 × 0.45 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.909, T max = 0.919

4897 measured reflections

3025 independent reflections

2525 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.06

3025 reflections

179 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.31 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/S1600536809053057/bt5135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053057/bt5135Isup2.hkl

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

C15H17NO2S	Z = 2
Mr = 275.36	F(000) = 292
Triclinic, P1	Dx = 1.233 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.311 (1) Å	Cell parameters from 2279 reflections
b = 8.521 (1) Å	θ = 2.6–27.7°
c = 11.412 (1) Å	µ = 0.22 mm−1
α = 99.86 (1)°	T = 299 K
β = 97.62 (1)°	Prism, colourless
γ = 108.14 (1)°	0.45 × 0.45 × 0.40 mm
V = 741.60 (14) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3025 independent reflections
Radiation source: fine-focus sealed tube	2525 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→9
Tmin = 0.909, Tmax = 0.919	k = −10→10
4897 measured reflections	l = −14→13

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1701P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.025
3025 reflections	Δρmax = 0.27 e Å−3
179 parameters	Δρmin = −0.31 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.087 (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
S1	0.81313 (5)	1.06718 (5)	0.37422 (4)	0.04434 (17)
O1	0.91624 (16)	1.14988 (15)	0.49312 (11)	0.0528 (3)
O2	0.76542 (18)	1.16623 (17)	0.29675 (13)	0.0587 (4)
N1	0.92841 (19)	0.9671 (2)	0.30816 (13)	0.0485 (4)
H1N	0.977 (3)	0.928 (3)	0.3581 (17)	0.058*
C1	0.6248 (2)	0.9101 (2)	0.38708 (15)	0.0413 (4)
C2	0.4799 (2)	0.8575 (3)	0.29635 (18)	0.0550 (5)
H2	0.4794	0.9097	0.2312	0.066*
C3	0.3358 (2)	0.7272 (3)	0.3029 (2)	0.0612 (5)
H3	0.2378	0.6926	0.2418	0.073*
C4	0.3338 (2)	0.6468 (2)	0.3982 (2)	0.0565 (5)
C5	0.4797 (3)	0.7038 (3)	0.4893 (2)	0.0617 (5)
H5	0.4794	0.6531	0.5552	0.074*
C6	0.6256 (2)	0.8341 (2)	0.48470 (17)	0.0541 (5)
H6	0.7230	0.8701	0.5464	0.065*
C7	0.8582 (2)	0.8517 (2)	0.19231 (15)	0.0457 (4)
C8	0.8165 (3)	0.9108 (3)	0.09055 (17)	0.0566 (5)
H8	0.8323	1.0252	0.0976	0.068*
C9	0.7514 (3)	0.7991 (3)	−0.02150 (18)	0.0640 (5)
C10	0.7315 (3)	0.6301 (3)	−0.03010 (19)	0.0695 (6)
H10	0.6872	0.5549	−0.1054	0.083*
C11	0.7759 (3)	0.5689 (3)	0.07052 (19)	0.0629 (5)
C12	0.8382 (2)	0.6827 (3)	0.18233 (17)	0.0530 (4)
H12	0.8668	0.6447	0.2512	0.064*
C13	0.1768 (3)	0.5018 (3)	0.4026 (3)	0.0824 (8)
H13A	0.0804	0.5406	0.4061	0.099*
H13B	0.1993	0.4592	0.4734	0.099*
H13C	0.1505	0.4131	0.3313	0.099*
C14	0.7039 (4)	0.8623 (4)	−0.1327 (2)	0.0946 (9)
H14A	0.5812	0.8369	−0.1510	0.113*
H14B	0.7392	0.8075	−0.2003	0.113*
H14C	0.7613	0.9827	−0.1174	0.113*
C15	0.7573 (4)	0.3850 (3)	0.0585 (3)	0.0952 (9)
H15A	0.6505	0.3153	0.0046	0.114*
H15B	0.7577	0.3579	0.1368	0.114*
H15C	0.8520	0.3645	0.0266	0.114*

	U11	U22	U33	U12	U13	U23
S1	0.0445 (3)	0.0386 (2)	0.0471 (3)	0.00888 (17)	0.00667 (18)	0.01407 (18)
O1	0.0526 (7)	0.0424 (7)	0.0528 (7)	0.0073 (5)	0.0022 (6)	0.0067 (6)
O2	0.0648 (8)	0.0499 (7)	0.0652 (8)	0.0178 (6)	0.0106 (7)	0.0280 (7)
N1	0.0437 (8)	0.0558 (9)	0.0448 (8)	0.0144 (7)	0.0068 (6)	0.0145 (7)
C1	0.0405 (8)	0.0376 (8)	0.0448 (9)	0.0119 (7)	0.0082 (7)	0.0093 (7)
C2	0.0479 (10)	0.0609 (12)	0.0535 (11)	0.0149 (9)	0.0042 (8)	0.0176 (9)
C3	0.0420 (10)	0.0599 (12)	0.0691 (13)	0.0089 (8)	0.0020 (9)	0.0045 (10)
C4	0.0468 (10)	0.0402 (9)	0.0802 (14)	0.0109 (8)	0.0223 (9)	0.0072 (9)
C5	0.0647 (12)	0.0540 (11)	0.0706 (13)	0.0150 (9)	0.0225 (10)	0.0281 (10)
C6	0.0514 (10)	0.0519 (10)	0.0546 (11)	0.0096 (8)	0.0049 (8)	0.0203 (9)
C7	0.0406 (9)	0.0540 (10)	0.0431 (9)	0.0136 (7)	0.0111 (7)	0.0153 (8)
C8	0.0644 (12)	0.0592 (12)	0.0521 (11)	0.0235 (10)	0.0135 (9)	0.0224 (9)
C9	0.0738 (14)	0.0770 (14)	0.0473 (11)	0.0312 (11)	0.0081 (9)	0.0224 (10)
C10	0.0846 (15)	0.0734 (14)	0.0468 (11)	0.0286 (12)	0.0047 (10)	0.0075 (10)
C11	0.0757 (14)	0.0589 (12)	0.0533 (11)	0.0238 (10)	0.0093 (10)	0.0123 (9)
C12	0.0574 (11)	0.0605 (11)	0.0465 (10)	0.0229 (9)	0.0109 (8)	0.0207 (9)
C13	0.0585 (13)	0.0538 (12)	0.130 (2)	0.0071 (10)	0.0356 (14)	0.0180 (14)
C14	0.126 (2)	0.113 (2)	0.0554 (14)	0.0512 (19)	0.0057 (14)	0.0353 (14)
C15	0.140 (3)	0.0633 (15)	0.0771 (17)	0.0353 (16)	0.0095 (17)	0.0107 (13)

S1—O2	1.4220 (13)	C8—C9	1.383 (3)
S1—O1	1.4353 (13)	C8—H8	0.9300
S1—N1	1.6414 (16)	C9—C10	1.382 (3)
S1—C1	1.7570 (17)	C9—C14	1.513 (3)
N1—C7	1.431 (2)	C10—C11	1.393 (3)
N1—H1N	0.830 (15)	C10—H10	0.9300
C1—C2	1.378 (2)	C11—C12	1.388 (3)
C1—C6	1.381 (2)	C11—C15	1.506 (3)
C2—C3	1.378 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.381 (3)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.382 (3)	C14—H14A	0.9600
C4—C13	1.506 (3)	C14—H14B	0.9600
C5—C6	1.380 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C12	1.380 (3)	C15—H15C	0.9600
C7—C8	1.387 (2)
O2—S1—O1	119.35 (8)	C7—C8—H8	120.1
O2—S1—N1	108.43 (8)	C10—C9—C8	119.03 (19)
O1—S1—N1	104.34 (8)	C10—C9—C14	120.8 (2)
O2—S1—C1	108.50 (8)	C8—C9—C14	120.1 (2)
O1—S1—C1	109.14 (8)	C9—C10—C11	122.0 (2)
N1—S1—C1	106.34 (8)	C9—C10—H10	119.0
C7—N1—S1	120.83 (12)	C11—C10—H10	119.0
C7—N1—H1N	112.8 (15)	C12—C11—C10	117.9 (2)
S1—N1—H1N	109.6 (15)	C12—C11—C15	121.0 (2)
C2—C1—C6	120.44 (16)	C10—C11—C15	121.1 (2)
C2—C1—S1	119.58 (13)	C7—C12—C11	120.66 (17)
C6—C1—S1	119.90 (13)	C7—C12—H12	119.7
C3—C2—C1	119.53 (18)	C11—C12—H12	119.7
C3—C2—H2	120.2	C4—C13—H13A	109.5
C1—C2—H2	120.2	C4—C13—H13B	109.5
C2—C3—C4	121.32 (18)	H13A—C13—H13B	109.5
C2—C3—H3	119.3	C4—C13—H13C	109.5
C4—C3—H3	119.3	H13A—C13—H13C	109.5
C5—C4—C3	118.06 (17)	H13B—C13—H13C	109.5
C5—C4—C13	121.2 (2)	C9—C14—H14A	109.5
C3—C4—C13	120.7 (2)	C9—C14—H14B	109.5
C4—C5—C6	121.66 (19)	H14A—C14—H14B	109.5
C4—C5—H5	119.2	C9—C14—H14C	109.5
C6—C5—H5	119.2	H14A—C14—H14C	109.5
C5—C6—C1	118.96 (18)	H14B—C14—H14C	109.5
C5—C6—H6	120.5	C11—C15—H15A	109.5
C1—C6—H6	120.5	C11—C15—H15B	109.5
C12—C7—C8	120.51 (18)	H15A—C15—H15B	109.5
C12—C7—N1	119.34 (16)	C11—C15—H15C	109.5
C8—C7—N1	120.11 (17)	H15A—C15—H15C	109.5
C9—C8—C7	119.83 (19)	H15B—C15—H15C	109.5
C9—C8—H8	120.1
O2—S1—N1—C7	−59.70 (15)	C2—C1—C6—C5	0.6 (3)
O1—S1—N1—C7	172.11 (13)	S1—C1—C6—C5	−176.08 (15)
C1—S1—N1—C7	56.80 (15)	S1—N1—C7—C12	−116.91 (17)
O2—S1—C1—C2	24.58 (17)	S1—N1—C7—C8	65.4 (2)
O1—S1—C1—C2	156.11 (15)	C12—C7—C8—C9	1.2 (3)
N1—S1—C1—C2	−91.87 (16)	N1—C7—C8—C9	178.92 (17)
O2—S1—C1—C6	−158.72 (15)	C7—C8—C9—C10	−1.0 (3)
O1—S1—C1—C6	−27.19 (17)	C7—C8—C9—C14	179.4 (2)
N1—S1—C1—C6	84.83 (16)	C8—C9—C10—C11	−0.3 (4)
C6—C1—C2—C3	−0.6 (3)	C14—C9—C10—C11	179.3 (2)
S1—C1—C2—C3	176.04 (15)	C9—C10—C11—C12	1.4 (4)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C11—C15	−178.5 (3)
C2—C3—C4—C5	1.6 (3)	C8—C7—C12—C11	−0.1 (3)
C2—C3—C4—C13	−178.55 (19)	N1—C7—C12—C11	−177.81 (17)
C3—C4—C5—C6	−1.7 (3)	C10—C11—C12—C7	−1.2 (3)
C13—C4—C5—C6	178.5 (2)	C15—C11—C12—C7	178.7 (2)
C4—C5—C6—C1	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.11 (2)	2.933 (2)	170 (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)	2.11 (2)	2.933 (2)	170 (2)

Symmetry code: (i) .