N-(2,6-Dimethyl-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(15)H(17)NO(2)S, the mol-ecule is bent at the S atom, the C-SO(2)-NH-C torsion angle being 88.0 (2)°. The dihedral angle between the two aromatic rings is 49.8 (1)°. In the crystal, mol-ecules are linked into zigzag chains parallel to the a axis via N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study of the effect of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 5.1412 (5) Å

b = 17.310 (2) Å

c = 16.429 (2) Å

β = 96.65 (1)°

V = 1452.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.46 × 0.32 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector.

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.906, T max = 0.970

7741 measured reflections

2580 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

2580 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.36 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/S1600536810014571/vm2025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014571/vm2025Isup2.hkl

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

C15H17NO2S	F(000) = 584
Mr = 275.36	Dx = 1.259 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2102 reflections
a = 5.1412 (5) Å	θ = 2.5–27.7°
b = 17.310 (2) Å	µ = 0.22 mm−1
c = 16.429 (2) Å	T = 299 K
β = 96.65 (1)°	Prism, colourless
V = 1452.2 (3) Å3	0.46 × 0.32 × 0.14 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector.	2580 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
graphite	Rint = 0.052
Rotation method data acquisition using ω and phi scans.	θmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.906, Tmax = 0.970	k = −20→20
7741 measured reflections	l = −18→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.6128P] where P = (Fo2 + 2Fc2)/3
2580 reflections	(Δ/σ)max = 0.011
178 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.35 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.0076 (4)	0.79081 (11)	0.32294 (13)	0.0373 (5)
C2	0.1791 (5)	0.79695 (14)	0.39383 (14)	0.0499 (6)
H2	0.3173	0.8319	0.3971	0.060*
C3	0.1426 (5)	0.75041 (15)	0.45988 (15)	0.0571 (6)
H3	0.2573	0.7546	0.5078	0.069*
C4	−0.0596 (5)	0.69793 (14)	0.45655 (15)	0.0537 (6)
C5	−0.2303 (5)	0.69408 (15)	0.38508 (17)	0.0580 (7)
H5	−0.3706	0.6599	0.3821	0.070*
C6	−0.1976 (4)	0.73955 (13)	0.31845 (15)	0.0487 (5)
H6	−0.3133	0.7357	0.2707	0.058*
C7	−0.0218 (4)	0.99486 (12)	0.27900 (14)	0.0416 (5)
C8	−0.1053 (4)	1.01478 (14)	0.35381 (15)	0.0499 (6)
C9	−0.0115 (6)	1.08314 (17)	0.39028 (19)	0.0747 (8)
H9	−0.0666	1.0982	0.4398	0.090*
C10	0.1617 (7)	1.12894 (18)	0.3544 (3)	0.0913 (11)
H10	0.2274	1.1736	0.3807	0.110*
C11	0.2372 (6)	1.10901 (16)	0.2804 (3)	0.0823 (10)
H11	0.3537	1.1407	0.2567	0.099*
C12	0.1440 (5)	1.04222 (13)	0.23938 (18)	0.0575 (7)
C13	−0.0937 (7)	0.6450 (2)	0.5270 (2)	0.0861 (10)
H13A	−0.0207	0.6687	0.5773	0.103*
H13B	−0.0054	0.5970	0.5198	0.103*
H13C	−0.2768	0.6353	0.5289	0.103*
C14	−0.2972 (5)	0.96625 (16)	0.39423 (16)	0.0607 (7)
H14A	−0.2435	0.9131	0.3945	0.073*
H14B	−0.4683	0.9712	0.3644	0.073*
H14C	−0.3021	0.9836	0.4495	0.073*
C15	0.2180 (6)	1.02526 (17)	0.1559 (2)	0.0785 (9)
H15A	0.0714	1.0027	0.1228	0.094*
H15B	0.3626	0.9898	0.1603	0.094*
H15C	0.2675	1.0724	0.1309	0.094*
N1	−0.1189 (3)	0.92553 (10)	0.23762 (11)	0.0406 (4)
H1N	−0.281 (2)	0.9160 (14)	0.2363 (14)	0.049*
O1	0.3230 (3)	0.86960 (9)	0.24338 (10)	0.0492 (4)
O2	−0.0551 (3)	0.80389 (9)	0.16625 (10)	0.0554 (4)
S1	0.05387 (10)	0.84674 (3)	0.23607 (3)	0.03851 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0356 (11)	0.0335 (10)	0.0442 (11)	0.0020 (9)	0.0100 (8)	−0.0017 (9)
C2	0.0488 (13)	0.0495 (13)	0.0513 (13)	−0.0121 (11)	0.0052 (10)	0.0000 (11)
C3	0.0612 (15)	0.0641 (15)	0.0454 (13)	−0.0033 (13)	0.0033 (11)	0.0023 (12)
C4	0.0602 (15)	0.0513 (14)	0.0529 (14)	0.0018 (12)	0.0212 (11)	0.0051 (11)
C5	0.0527 (14)	0.0510 (14)	0.0727 (17)	−0.0149 (12)	0.0175 (12)	0.0064 (13)
C6	0.0434 (12)	0.0475 (12)	0.0550 (14)	−0.0075 (11)	0.0049 (10)	0.0010 (11)
C7	0.0352 (11)	0.0332 (10)	0.0554 (13)	0.0062 (9)	0.0011 (9)	0.0055 (9)
C8	0.0462 (13)	0.0463 (13)	0.0551 (14)	0.0088 (11)	−0.0037 (10)	−0.0043 (11)
C9	0.081 (2)	0.0580 (16)	0.080 (2)	0.0120 (16)	−0.0092 (16)	−0.0198 (15)
C10	0.090 (2)	0.0443 (16)	0.132 (3)	−0.0081 (16)	−0.018 (2)	−0.0160 (19)
C11	0.0689 (19)	0.0416 (15)	0.136 (3)	−0.0097 (14)	0.0094 (19)	0.0171 (18)
C12	0.0478 (14)	0.0377 (12)	0.0872 (19)	0.0043 (11)	0.0088 (12)	0.0190 (12)
C13	0.103 (2)	0.090 (2)	0.0696 (19)	−0.0100 (19)	0.0280 (17)	0.0248 (17)
C14	0.0623 (16)	0.0715 (17)	0.0504 (14)	0.0100 (13)	0.0157 (11)	−0.0022 (13)
C15	0.082 (2)	0.0637 (17)	0.098 (2)	0.0144 (15)	0.0422 (17)	0.0360 (17)
N1	0.0308 (8)	0.0399 (9)	0.0509 (10)	−0.0004 (8)	0.0039 (8)	0.0021 (8)
O1	0.0343 (8)	0.0494 (9)	0.0662 (10)	0.0025 (7)	0.0162 (7)	0.0091 (8)
O2	0.0681 (11)	0.0544 (10)	0.0442 (9)	−0.0033 (8)	0.0087 (7)	−0.0100 (8)
S1	0.0364 (3)	0.0375 (3)	0.0431 (3)	0.0002 (2)	0.0108 (2)	−0.0002 (2)

C1—C6	1.374 (3)	C10—C11	1.362 (5)
C1—C2	1.381 (3)	C10—H10	0.9300
C1—S1	1.763 (2)	C11—C12	1.395 (4)
C2—C3	1.382 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C15	1.495 (4)
C3—C4	1.377 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.384 (4)	C13—H13C	0.9600
C4—C13	1.503 (4)	C14—H14A	0.9600
C5—C6	1.374 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.391 (3)	C15—H15B	0.9600
C7—C12	1.397 (3)	C15—H15C	0.9600
C7—N1	1.440 (3)	N1—S1	1.6294 (18)
C8—C9	1.387 (4)	N1—H1N	0.848 (10)
C8—C14	1.507 (3)	O1—S1	1.4308 (15)
C9—C10	1.375 (5)	O2—S1	1.4251 (16)
C9—H9	0.9300
C6—C1—C2	120.4 (2)	C12—C11—H11	119.2
C6—C1—S1	119.08 (17)	C11—C12—C7	117.1 (3)
C2—C1—S1	120.50 (16)	C11—C12—C15	119.8 (3)
C1—C2—C3	119.1 (2)	C7—C12—C15	123.1 (2)
C1—C2—H2	120.5	C4—C13—H13A	109.5
C3—C2—H2	120.5	C4—C13—H13B	109.5
C4—C3—C2	121.6 (2)	H13A—C13—H13B	109.5
C4—C3—H3	119.2	C4—C13—H13C	109.5
C2—C3—H3	119.2	H13A—C13—H13C	109.5
C3—C4—C5	117.9 (2)	H13B—C13—H13C	109.5
C3—C4—C13	121.8 (3)	C8—C14—H14A	109.5
C5—C4—C13	120.3 (2)	C8—C14—H14B	109.5
C6—C5—C4	121.6 (2)	H14A—C14—H14B	109.5
C6—C5—H5	119.2	C8—C14—H14C	109.5
C4—C5—H5	119.2	H14A—C14—H14C	109.5
C1—C6—C5	119.4 (2)	H14B—C14—H14C	109.5
C1—C6—H6	120.3	C12—C15—H15A	109.5
C5—C6—H6	120.3	C12—C15—H15B	109.5
C8—C7—C12	122.2 (2)	H15A—C15—H15B	109.5
C8—C7—N1	119.88 (19)	C12—C15—H15C	109.5
C12—C7—N1	117.8 (2)	H15A—C15—H15C	109.5
C9—C8—C7	117.8 (3)	H15B—C15—H15C	109.5
C9—C8—C14	119.8 (2)	C7—N1—S1	123.04 (13)
C7—C8—C14	122.4 (2)	C7—N1—H1N	117.4 (16)
C10—C9—C8	121.1 (3)	S1—N1—H1N	111.9 (17)
C10—C9—H9	119.5	O2—S1—O1	119.85 (10)
C8—C9—H9	119.5	O2—S1—N1	106.49 (10)
C11—C10—C9	120.1 (3)	O1—S1—N1	106.91 (9)
C11—C10—H10	119.9	O2—S1—C1	106.76 (10)
C9—C10—H10	119.9	O1—S1—C1	107.68 (10)
C10—C11—C12	121.6 (3)	N1—S1—C1	108.79 (9)
C10—C11—H11	119.2
C6—C1—C2—C3	0.5 (3)	C10—C11—C12—C7	−2.6 (4)
S1—C1—C2—C3	−177.81 (18)	C10—C11—C12—C15	176.0 (3)
C1—C2—C3—C4	0.3 (4)	C8—C7—C12—C11	3.8 (3)
C2—C3—C4—C5	−1.3 (4)	N1—C7—C12—C11	−179.8 (2)
C2—C3—C4—C13	177.5 (3)	C8—C7—C12—C15	−174.7 (2)
C3—C4—C5—C6	1.5 (4)	N1—C7—C12—C15	1.7 (3)
C13—C4—C5—C6	−177.3 (3)	C8—C7—N1—S1	−103.9 (2)
C2—C1—C6—C5	−0.3 (3)	C12—C7—N1—S1	79.6 (2)
S1—C1—C6—C5	178.06 (18)	C7—N1—S1—O2	−157.30 (17)
C4—C5—C6—C1	−0.8 (4)	C7—N1—S1—O1	−28.06 (19)
C12—C7—C8—C9	−2.0 (3)	C7—N1—S1—C1	87.97 (18)
N1—C7—C8—C9	−178.4 (2)	C6—C1—S1—O2	−26.8 (2)
C12—C7—C8—C14	176.2 (2)	C2—C1—S1—O2	151.58 (18)
N1—C7—C8—C14	−0.2 (3)	C6—C1—S1—O1	−156.66 (17)
C7—C8—C9—C10	−1.1 (4)	C2—C1—S1—O1	21.7 (2)
C14—C8—C9—C10	−179.3 (3)	C6—C1—S1—N1	87.81 (19)
C8—C9—C10—C11	2.3 (5)	C2—C1—S1—N1	−93.86 (19)
C9—C10—C11—C12	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.20 (1)	3.040 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.20 (1)	3.040 (2)	169 (2)

Symmetry code: (i) .