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

In the crystal structure of the title compound, C(15)H(17)NO(2)S, the conformations of the N-C bond in the C-SO(2)-NH-C segment are trans and gauche, respectively, 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 -61.8 (2)°. Furthermore, the conformation of the N-H bond and the 3-methyl group in the aniline benzene ring are nearly anti to each other. The dihedral angle between the benzene rings is 47.8 (1)°. In the crystal, N-H⋯O hydrogen bonds link the molecules into chains.

Related literature

For the preparation of the compound, see: Shetty & Gowda (2005 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008a ▶,b ▶; 2009 ▶); Perlovich et al. (2006 ▶)

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 9.2528 (7) Å

b = 15.329 (1) Å

c = 10.4469 (7) Å

β = 102.558 (7)°

V = 1446.30 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.45 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.907, T max = 0.929

10438 measured reflections

2902 independent reflections

2360 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.06

2902 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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/S1600536809010459/fl2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010459/fl2240Isup2.hkl

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

C15H17NO2S	F(000) = 584
Mr = 275.36	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5065 reflections
a = 9.2528 (7) Å	θ = 2.3–27.3°
b = 15.329 (1) Å	µ = 0.22 mm−1
c = 10.4469 (7) Å	T = 299 K
β = 102.558 (7)°	Prism, colourless
V = 1446.30 (17) Å3	0.45 × 0.40 × 0.34 mm
Z = 4

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2360 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→11
Tmin = 0.907, Tmax = 0.929	k = −19→19
10438 measured reflections	l = −13→12

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) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.5487P] where P = (Fo2 + 2Fc2)/3
2902 reflections	(Δ/σ)max = 0.014
175 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Experimental. 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
C1	0.0832 (2)	0.11183 (12)	0.41984 (18)	0.0420 (4)
C2	0.2056 (3)	0.08904 (16)	0.5149 (2)	0.0618 (6)
H2	0.2382	0.1249	0.5872	0.074*
C3	0.2793 (3)	0.01242 (17)	0.5015 (2)	0.0676 (7)
H3	0.3623	−0.0027	0.5653	0.081*
C4	0.2330 (3)	−0.04188 (14)	0.3963 (2)	0.0539 (5)
C5	0.1119 (3)	−0.01764 (17)	0.3024 (3)	0.0703 (7)
H5	0.0800	−0.0534	0.2299	0.084*
C6	0.0366 (3)	0.05845 (16)	0.3129 (2)	0.0640 (6)
H6	−0.0454	0.0737	0.2481	0.077*
C7	0.2234 (2)	0.30486 (12)	0.40062 (17)	0.0395 (4)
C8	0.2693 (2)	0.35604 (12)	0.51153 (18)	0.0457 (5)
H8	0.1995	0.3769	0.5560	0.055*
C9	0.4176 (2)	0.37672 (12)	0.55727 (19)	0.0485 (5)
C10	0.5221 (2)	0.34840 (13)	0.4878 (2)	0.0489 (5)
C11	0.4742 (2)	0.29740 (14)	0.3767 (2)	0.0522 (5)
H11	0.5430	0.2777	0.3304	0.063*
C12	0.3270 (2)	0.27524 (13)	0.33332 (19)	0.0468 (5)
H12	0.2976	0.2406	0.2592	0.056*
C13	0.3163 (3)	−0.12473 (17)	0.3828 (3)	0.0770 (8)
H13A	0.3446	−0.1526	0.4668	0.092*
H13B	0.4033	−0.1111	0.3507	0.092*
H13C	0.2540	−0.1632	0.3223	0.092*
C14	0.4651 (3)	0.42967 (18)	0.6811 (2)	0.0709 (7)
H14A	0.3803	0.4426	0.7167	0.085*
H14B	0.5098	0.4831	0.6614	0.085*
H14C	0.5355	0.3969	0.7440	0.085*
C15	0.6836 (3)	0.37166 (18)	0.5317 (3)	0.0703 (7)
H15A	0.7240	0.3435	0.6138	0.084*
H15B	0.6935	0.4337	0.5422	0.084*
H15C	0.7361	0.3525	0.4670	0.084*
N1	0.06920 (18)	0.28438 (10)	0.35435 (15)	0.0435 (4)
H1N	0.0181	0.3106	0.2867	0.052*
O1	−0.15757 (16)	0.20372 (11)	0.35826 (15)	0.0568 (4)
O2	0.02022 (16)	0.23588 (11)	0.56602 (12)	0.0528 (4)
S1	−0.00854 (5)	0.21086 (3)	0.43102 (4)	0.04195 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0434 (10)	0.0444 (10)	0.0383 (9)	−0.0001 (8)	0.0092 (8)	0.0027 (8)
C2	0.0734 (15)	0.0639 (14)	0.0413 (11)	0.0187 (12)	−0.0029 (10)	−0.0019 (10)
C3	0.0755 (16)	0.0693 (15)	0.0529 (13)	0.0232 (13)	0.0030 (12)	0.0091 (11)
C4	0.0597 (13)	0.0427 (10)	0.0653 (13)	0.0000 (9)	0.0264 (11)	0.0074 (10)
C5	0.0685 (15)	0.0616 (14)	0.0763 (17)	−0.0044 (12)	0.0057 (13)	−0.0236 (12)
C6	0.0542 (13)	0.0652 (14)	0.0641 (14)	0.0050 (11)	−0.0057 (11)	−0.0163 (11)
C7	0.0498 (11)	0.0377 (9)	0.0295 (8)	0.0055 (8)	0.0058 (7)	0.0037 (7)
C8	0.0596 (12)	0.0420 (10)	0.0360 (9)	0.0058 (9)	0.0114 (8)	−0.0013 (8)
C9	0.0655 (13)	0.0388 (10)	0.0375 (10)	−0.0009 (9)	0.0030 (9)	0.0002 (8)
C10	0.0520 (11)	0.0421 (10)	0.0486 (11)	0.0011 (9)	0.0022 (9)	0.0074 (9)
C11	0.0552 (12)	0.0548 (12)	0.0492 (12)	0.0074 (10)	0.0167 (10)	0.0008 (9)
C12	0.0583 (12)	0.0490 (11)	0.0326 (9)	0.0028 (9)	0.0085 (8)	−0.0041 (8)
C13	0.0853 (18)	0.0517 (13)	0.101 (2)	0.0086 (13)	0.0348 (16)	0.0037 (13)
C14	0.0883 (18)	0.0665 (15)	0.0534 (13)	−0.0132 (13)	0.0054 (12)	−0.0177 (11)
C15	0.0580 (14)	0.0666 (15)	0.0796 (17)	−0.0008 (12)	0.0001 (12)	0.0024 (13)
N1	0.0493 (9)	0.0485 (9)	0.0294 (7)	0.0078 (7)	0.0015 (7)	0.0064 (6)
O1	0.0413 (8)	0.0772 (11)	0.0495 (8)	0.0071 (7)	0.0042 (6)	−0.0027 (7)
O2	0.0600 (9)	0.0693 (9)	0.0299 (7)	0.0067 (7)	0.0118 (6)	−0.0016 (6)
S1	0.0414 (3)	0.0537 (3)	0.0298 (3)	0.0059 (2)	0.00563 (18)	−0.00009 (18)

C1—C6	1.376 (3)	C10—C11	1.389 (3)
C1—C2	1.379 (3)	C10—C15	1.507 (3)
C1—S1	1.7557 (19)	C11—C12	1.381 (3)
C2—C3	1.380 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.371 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.370 (3)	C13—H13C	0.9600
C4—C13	1.508 (3)	C14—H14A	0.9600
C5—C6	1.375 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C12	1.382 (3)	C15—H15B	0.9600
C7—C8	1.387 (3)	C15—H15C	0.9600
C7—N1	1.438 (2)	N1—S1	1.6369 (17)
C8—C9	1.388 (3)	N1—H1N	0.8600
C8—H8	0.9300	O1—S1	1.4267 (15)
C9—C10	1.398 (3)	O2—S1	1.4296 (13)
C9—C14	1.509 (3)
C6—C1—C2	119.82 (19)	C10—C11—H11	119.2
C6—C1—S1	119.82 (16)	C11—C12—C7	119.70 (18)
C2—C1—S1	120.30 (15)	C11—C12—H12	120.1
C1—C2—C3	119.3 (2)	C7—C12—H12	120.1
C1—C2—H2	120.4	C4—C13—H13A	109.5
C3—C2—H2	120.4	C4—C13—H13B	109.5
C4—C3—C2	121.5 (2)	H13A—C13—H13B	109.5
C4—C3—H3	119.3	C4—C13—H13C	109.5
C2—C3—H3	119.3	H13A—C13—H13C	109.5
C5—C4—C3	118.3 (2)	H13B—C13—H13C	109.5
C5—C4—C13	121.1 (2)	C9—C14—H14A	109.5
C3—C4—C13	120.6 (2)	C9—C14—H14B	109.5
C4—C5—C6	121.5 (2)	H14A—C14—H14B	109.5
C4—C5—H5	119.3	C9—C14—H14C	109.5
C6—C5—H5	119.3	H14A—C14—H14C	109.5
C5—C6—C1	119.6 (2)	H14B—C14—H14C	109.5
C5—C6—H6	120.2	C10—C15—H15A	109.5
C1—C6—H6	120.2	C10—C15—H15B	109.5
C12—C7—C8	119.37 (19)	H15A—C15—H15B	109.5
C12—C7—N1	120.27 (17)	C10—C15—H15C	109.5
C8—C7—N1	120.34 (17)	H15A—C15—H15C	109.5
C7—C8—C9	121.13 (19)	H15B—C15—H15C	109.5
C7—C8—H8	119.4	C7—N1—S1	119.68 (12)
C9—C8—H8	119.4	C7—N1—H1N	120.2
C8—C9—C10	119.58 (18)	S1—N1—H1N	120.2
C8—C9—C14	120.0 (2)	O1—S1—O2	119.82 (9)
C10—C9—C14	120.4 (2)	O1—S1—N1	105.59 (9)
C11—C10—C9	118.52 (19)	O2—S1—N1	106.90 (9)
C11—C10—C15	120.1 (2)	O1—S1—C1	108.88 (9)
C9—C10—C15	121.3 (2)	O2—S1—C1	107.97 (9)
C12—C11—C10	121.7 (2)	N1—S1—C1	107.01 (9)
C12—C11—H11	119.2
C6—C1—C2—C3	−0.4 (4)	C14—C9—C10—C15	−1.7 (3)
S1—C1—C2—C3	−177.58 (19)	C9—C10—C11—C12	0.7 (3)
C1—C2—C3—C4	−0.4 (4)	C15—C10—C11—C12	−179.7 (2)
C2—C3—C4—C5	1.0 (4)	C10—C11—C12—C7	0.6 (3)
C2—C3—C4—C13	179.2 (2)	C8—C7—C12—C11	−0.4 (3)
C3—C4—C5—C6	−0.8 (4)	N1—C7—C12—C11	178.19 (17)
C13—C4—C5—C6	−179.0 (2)	C12—C7—N1—S1	105.46 (18)
C4—C5—C6—C1	0.0 (4)	C8—C7—N1—S1	−75.9 (2)
C2—C1—C6—C5	0.6 (4)	C7—N1—S1—O1	−177.68 (14)
S1—C1—C6—C5	177.8 (2)	C7—N1—S1—O2	53.68 (16)
C12—C7—C8—C9	−1.1 (3)	C7—N1—S1—C1	−61.80 (15)
N1—C7—C8—C9	−179.75 (16)	C6—C1—S1—O1	26.4 (2)
C7—C8—C9—C10	2.5 (3)	C2—C1—S1—O1	−156.35 (18)
C7—C8—C9—C14	−177.67 (19)	C6—C1—S1—O2	157.99 (18)
C8—C9—C10—C11	−2.3 (3)	C2—C1—S1—O2	−24.8 (2)
C14—C9—C10—C11	177.9 (2)	C6—C1—S1—N1	−87.25 (19)
C8—C9—C10—C15	178.14 (19)	C2—C1—S1—N1	89.97 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.42	2.963 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.42	2.963 (2)	122

Symmetry code: (i) .