N-(2,5-Dimethyl-phen-yl)-4-methyl-benzene-sulfonamide.

In the crystal structure of the title compound, C(15)H(17)NO(2)S, the conformation of the N-C bond in the C-SO(2)-NH-C segment has gauche torsions with respect to the S=O bonds. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of -61.0 (2)°. The dihedral angle between the two aromatic rings is 49.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For our study of the effects of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶)

Experimental

Crystal data

C15H17NO2S

M = 275.36

Triclinic,

a = 8.6397 (7) Å

b = 9.7067 (8) Å

c = 10.518 (1) Å

α = 66.97 (1)°

β = 81.37 (1)°

γ = 64.82 (1)°

V = 734.47 (11) Å3

Z = 2

Cu Kα radiation

μ = 1.94 mm−1

T = 299 K

0.50 × 0.30 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scans (North et al., 1968 ▶) T min = 0.444, T max = 0.861

3926 measured reflections

2603 independent reflections

2324 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.18

2603 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.46 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/S1600536809051174/ng2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051174/ng2695Isup2.hkl

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

C15H17NO2S	Z = 2
Mr = 275.36	F(000) = 292
Triclinic, P1	Dx = 1.245 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.6397 (7) Å	Cell parameters from 25 reflections
b = 9.7067 (8) Å	θ = 7.2–23.8°
c = 10.518 (1) Å	µ = 1.94 mm−1
α = 66.97 (1)°	T = 299 K
β = 81.37 (1)°	Prism, colourless
γ = 64.82 (1)°	0.50 × 0.30 × 0.08 mm
V = 734.47 (11) Å3

Enraf–Nonius CAD-4 diffractometer	2324 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 66.9°, θmin = 4.6°
ω/2θ scans	h = −10→4
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.444, Tmax = 0.861	l = −12→12
3926 measured reflections	3 standard reflections every 120 min
2603 independent reflections	intensity decay: 1.0%

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.2017P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max = 0.001
2603 reflections	Δρmax = 0.39 e Å−3
176 parameters	Δρmin = −0.46 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: 0.0133 (16)

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	1.05078 (6)	−0.00156 (6)	0.20853 (5)	0.0456 (2)
O1	1.1338 (2)	0.0247 (2)	0.07776 (16)	0.0591 (5)
O2	1.1518 (2)	−0.0780 (2)	0.33191 (16)	0.0560 (4)
N1	0.9516 (2)	−0.1130 (2)	0.21337 (18)	0.0487 (5)
H1N	0.9621	−0.1456	0.1462	0.058*
C1	0.8925 (3)	0.1869 (3)	0.2088 (2)	0.0451 (5)
C2	0.8295 (4)	0.3162 (3)	0.0855 (3)	0.0646 (7)
H2	0.8739	0.3063	0.0018	0.078*
C3	0.6998 (4)	0.4602 (3)	0.0887 (3)	0.0761 (8)
H3	0.6568	0.5471	0.0058	0.091*
C4	0.6323 (4)	0.4792 (3)	0.2106 (3)	0.0651 (7)
C5	0.6989 (3)	0.3478 (3)	0.3329 (3)	0.0574 (6)
H5	0.6554	0.3583	0.4166	0.069*
C6	0.8281 (3)	0.2021 (3)	0.3331 (2)	0.0494 (5)
H6	0.8713	0.1151	0.4159	0.059*
C7	0.8463 (3)	−0.1581 (3)	0.3284 (2)	0.0464 (5)
C8	0.6706 (3)	−0.0938 (3)	0.3112 (3)	0.0565 (6)
C9	0.5788 (4)	−0.1463 (4)	0.4267 (3)	0.0734 (8)
H9	0.4606	−0.1073	0.4188	0.088*
C10	0.6579 (4)	−0.2540 (4)	0.5520 (3)	0.0726 (8)
H10	0.5918	−0.2850	0.6270	0.087*
C11	0.8321 (4)	−0.3172 (3)	0.5696 (2)	0.0591 (6)
C12	0.9274 (3)	−0.2698 (3)	0.4553 (2)	0.0530 (6)
H12	1.0459	−0.3126	0.4633	0.064*
C13	0.4892 (5)	0.6354 (4)	0.2132 (4)	0.0963 (11)
H13A	0.4227	0.6898	0.1290	0.116*
H13B	0.5359	0.7052	0.2218	0.116*
H13C	0.4175	0.6112	0.2903	0.116*
C14	0.5794 (4)	0.0286 (4)	0.1766 (3)	0.0760 (8)
H14A	0.6140	−0.0205	0.1080	0.091*
H14B	0.6079	0.1218	0.1472	0.091*
H14C	0.4581	0.0628	0.1887	0.091*
C15	0.9181 (5)	−0.4357 (4)	0.7079 (3)	0.0797 (9)
H15A	0.8746	−0.5195	0.7457	0.096*
H15B	0.8949	−0.3784	0.7697	0.096*
H15C	1.0393	−0.4847	0.6962	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0435 (3)	0.0545 (3)	0.0279 (3)	−0.0142 (2)	0.0042 (2)	−0.0118 (2)
O1	0.0546 (9)	0.0812 (11)	0.0335 (9)	−0.0253 (9)	0.0123 (7)	−0.0194 (8)
O2	0.0487 (8)	0.0694 (10)	0.0350 (8)	−0.0145 (8)	−0.0046 (6)	−0.0129 (7)
N1	0.0570 (10)	0.0528 (10)	0.0319 (9)	−0.0178 (9)	0.0057 (8)	−0.0176 (8)
C1	0.0474 (11)	0.0474 (11)	0.0330 (11)	−0.0172 (9)	0.0009 (8)	−0.0095 (9)
C2	0.0807 (17)	0.0568 (14)	0.0341 (12)	−0.0163 (13)	−0.0006 (11)	−0.0066 (10)
C3	0.094 (2)	0.0539 (14)	0.0496 (16)	−0.0122 (14)	−0.0125 (14)	−0.0029 (12)
C4	0.0660 (15)	0.0511 (13)	0.0680 (18)	−0.0148 (12)	−0.0039 (13)	−0.0195 (12)
C5	0.0587 (14)	0.0623 (14)	0.0497 (14)	−0.0194 (12)	0.0053 (11)	−0.0258 (11)
C6	0.0531 (12)	0.0530 (12)	0.0331 (11)	−0.0165 (10)	0.0011 (9)	−0.0124 (9)
C7	0.0575 (12)	0.0447 (11)	0.0351 (11)	−0.0198 (10)	0.0058 (9)	−0.0153 (9)
C8	0.0596 (14)	0.0594 (13)	0.0472 (14)	−0.0244 (11)	0.0038 (11)	−0.0168 (11)
C9	0.0642 (16)	0.090 (2)	0.0663 (19)	−0.0395 (16)	0.0140 (14)	−0.0240 (16)
C10	0.087 (2)	0.088 (2)	0.0515 (16)	−0.0551 (17)	0.0204 (14)	−0.0198 (14)
C11	0.0856 (18)	0.0582 (14)	0.0406 (13)	−0.0417 (13)	0.0075 (12)	−0.0133 (11)
C12	0.0652 (14)	0.0490 (12)	0.0391 (12)	−0.0226 (11)	0.0016 (10)	−0.0112 (10)
C13	0.097 (2)	0.0616 (17)	0.103 (3)	−0.0021 (17)	−0.011 (2)	−0.0308 (18)
C14	0.0570 (15)	0.088 (2)	0.0616 (17)	−0.0218 (14)	−0.0052 (13)	−0.0117 (15)
C15	0.122 (3)	0.0820 (19)	0.0410 (15)	−0.063 (2)	−0.0003 (15)	−0.0031 (13)

S1—O2	1.4256 (16)	C8—C9	1.391 (4)
S1—O1	1.4341 (15)	C8—C14	1.503 (4)
S1—N1	1.625 (2)	C9—C10	1.371 (4)
S1—C1	1.758 (2)	C9—H9	0.9300
N1—C7	1.442 (3)	C10—C11	1.373 (4)
N1—H1N	0.8600	C10—H10	0.9300
C1—C6	1.379 (3)	C11—C12	1.388 (3)
C1—C2	1.382 (3)	C11—C15	1.510 (4)
C2—C3	1.379 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.374 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.388 (4)	C14—H14A	0.9600
C4—C13	1.502 (4)	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—C8	1.384 (3)	C15—H15C	0.9600
C7—C12	1.396 (3)
O2—S1—O1	118.99 (10)	C9—C8—C14	120.5 (2)
O2—S1—N1	108.50 (10)	C10—C9—C8	121.8 (3)
O1—S1—N1	105.30 (10)	C10—C9—H9	119.1
O2—S1—C1	107.99 (10)	C8—C9—H9	119.1
O1—S1—C1	108.74 (10)	C9—C10—C11	121.7 (2)
N1—S1—C1	106.69 (10)	C9—C10—H10	119.1
C7—N1—S1	121.11 (15)	C11—C10—H10	119.1
C7—N1—H1N	119.4	C10—C11—C12	117.7 (2)
S1—N1—H1N	119.4	C10—C11—C15	121.4 (3)
C6—C1—C2	120.6 (2)	C12—C11—C15	120.9 (3)
C6—C1—S1	119.18 (17)	C11—C12—C7	120.4 (2)
C2—C1—S1	120.17 (18)	C11—C12—H12	119.8
C3—C2—C1	118.9 (2)	C7—C12—H12	119.8
C3—C2—H2	120.6	C4—C13—H13A	109.5
C1—C2—H2	120.6	C4—C13—H13B	109.5
C4—C3—C2	122.0 (2)	H13A—C13—H13B	109.5
C4—C3—H3	119.0	C4—C13—H13C	109.5
C2—C3—H3	119.0	H13A—C13—H13C	109.5
C3—C4—C5	117.9 (2)	H13B—C13—H13C	109.5
C3—C4—C13	121.7 (3)	C8—C14—H14A	109.5
C5—C4—C13	120.4 (3)	C8—C14—H14B	109.5
C6—C5—C4	121.5 (2)	H14A—C14—H14B	109.5
C6—C5—H5	119.3	C8—C14—H14C	109.5
C4—C5—H5	119.3	H14A—C14—H14C	109.5
C1—C6—C5	119.2 (2)	H14B—C14—H14C	109.5
C1—C6—H6	120.4	C11—C15—H15A	109.5
C5—C6—H6	120.4	C11—C15—H15B	109.5
C8—C7—C12	121.7 (2)	H15A—C15—H15B	109.5
C8—C7—N1	120.3 (2)	C11—C15—H15C	109.5
C12—C7—N1	118.0 (2)	H15A—C15—H15C	109.5
C7—C8—C9	116.6 (2)	H15B—C15—H15C	109.5
C7—C8—C14	122.9 (2)
O2—S1—N1—C7	54.45 (18)	S1—C1—C6—C5	−177.31 (18)
O1—S1—N1—C7	−177.12 (16)	C4—C5—C6—C1	0.1 (4)
C1—S1—N1—C7	−61.67 (18)	S1—N1—C7—C8	111.3 (2)
O2—S1—C1—C6	−31.9 (2)	S1—N1—C7—C12	−69.9 (2)
O1—S1—C1—C6	−162.32 (18)	C12—C7—C8—C9	−0.1 (4)
N1—S1—C1—C6	84.6 (2)	N1—C7—C8—C9	178.7 (2)
O2—S1—C1—C2	150.3 (2)	C12—C7—C8—C14	178.9 (3)
O1—S1—C1—C2	19.9 (2)	N1—C7—C8—C14	−2.3 (4)
N1—S1—C1—C2	−93.2 (2)	C7—C8—C9—C10	1.1 (4)
C6—C1—C2—C3	−0.7 (4)	C14—C8—C9—C10	−177.9 (3)
S1—C1—C2—C3	177.0 (2)	C8—C9—C10—C11	−0.7 (5)
C1—C2—C3—C4	0.4 (5)	C9—C10—C11—C12	−0.7 (4)
C2—C3—C4—C5	0.1 (5)	C9—C10—C11—C15	−180.0 (3)
C2—C3—C4—C13	−179.0 (3)	C10—C11—C12—C7	1.7 (4)
C3—C4—C5—C6	−0.4 (4)	C15—C11—C12—C7	−179.0 (2)
C13—C4—C5—C6	178.8 (3)	C8—C7—C12—C11	−1.3 (4)
C2—C1—C6—C5	0.5 (4)	N1—C7—C12—C11	179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.28	2.957 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.28	2.957 (2)	135

Symmetry code: (i) .