N-(2,3-Dimethyl-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(15)H(17)NO(2)S, the dihedral angle between the aromatic rings is 38.3 (1)°. The conformation of the N-H bond is anti to the methyl groups in the adjacent aromatic ring. In the crystal, N-H⋯O hydrogen bonds link the molecules into infinite chains.

Related literature

For the 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. (2009a ▶,b ▶; 2010 ▶); For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶)

Experimental

Crystal data

C15H17NO2S

M = 275.36

Monoclinic,

a = 10.771 (1) Å

b = 13.357 (1) Å

c = 9.9667 (9) Å

β = 93.256 (8)°

V = 1431.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 299 K

0.40 × 0.28 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.916, T max = 0.948

5990 measured reflections

2924 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.05

2924 reflections

178 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.33 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/S1600536810048786/bq2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048786/bq2256Isup2.hkl

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

C15H17NO2S	F(000) = 584
Mr = 275.36	Dx = 1.278 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2134 reflections
a = 10.771 (1) Å	θ = 2.7–27.8°
b = 13.357 (1) Å	µ = 0.22 mm−1
c = 9.9667 (9) Å	T = 299 K
β = 93.256 (8)°	Rod, colourless
V = 1431.6 (2) Å3	0.40 × 0.28 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2924 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.916, Tmax = 0.948	k = −16→16
5990 measured reflections	l = −12→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.5306P] where P = (Fo2 + 2Fc2)/3
2924 reflections	(Δ/σ)max = 0.003
178 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

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
C1	0.8751 (2)	0.83403 (14)	0.00059 (18)	0.0416 (5)
C2	0.9745 (2)	0.79149 (16)	0.0754 (2)	0.0541 (6)
H2	0.9603	0.7533	0.1511	0.065*
C3	1.0950 (2)	0.80616 (18)	0.0367 (3)	0.0618 (6)
H3	1.1610	0.7773	0.0870	0.074*
C4	1.1192 (2)	0.86297 (18)	−0.0755 (2)	0.0597 (6)
C5	1.0186 (3)	0.90574 (18)	−0.1467 (2)	0.0615 (6)
H5	1.0330	0.9452	−0.2212	0.074*
C6	0.8977 (2)	0.89196 (16)	−0.1112 (2)	0.0532 (5)
H6	0.8320	0.9212	−0.1616	0.064*
C7	0.70153 (17)	0.61341 (14)	0.01859 (17)	0.0370 (4)
C8	0.62354 (17)	0.56874 (15)	0.10963 (17)	0.0388 (4)
C9	0.6555 (2)	0.47214 (16)	0.15710 (19)	0.0474 (5)
C10	0.7613 (2)	0.42509 (17)	0.1120 (2)	0.0566 (6)
H10	0.7829	0.3619	0.1450	0.068*
C11	0.8345 (2)	0.46986 (18)	0.0199 (2)	0.0574 (6)
H11	0.9033	0.4363	−0.0104	0.069*
C12	0.80522 (18)	0.56454 (16)	−0.0271 (2)	0.0468 (5)
H12	0.8543	0.5955	−0.0887	0.056*
C13	1.2511 (3)	0.8780 (2)	−0.1188 (3)	0.0863 (9)
H13A	1.3053	0.8298	−0.0743	0.104*
H13B	1.2788	0.9443	−0.0951	0.104*
H13C	1.2526	0.8693	−0.2143	0.104*
C14	0.50770 (19)	0.62004 (18)	0.1532 (2)	0.0541 (6)
H14A	0.4944	0.6807	0.1027	0.065*
H14B	0.5174	0.6356	0.2473	0.065*
H14C	0.4375	0.5764	0.1374	0.065*
C15	0.5750 (3)	0.4194 (2)	0.2541 (2)	0.0715 (8)
H15A	0.4917	0.4140	0.2150	0.086*
H15B	0.5744	0.4571	0.3361	0.086*
H15C	0.6077	0.3537	0.2728	0.086*
N1	0.66972 (16)	0.71156 (12)	−0.03365 (15)	0.0418 (4)
H1N	0.674 (2)	0.7188 (16)	−0.1175 (10)	0.050*
O1	0.72272 (15)	0.79141 (12)	0.18435 (13)	0.0561 (4)
O2	0.64468 (16)	0.89283 (12)	−0.01147 (17)	0.0629 (4)
S1	0.71972 (5)	0.81273 (4)	0.04301 (5)	0.04238 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0596 (12)	0.0339 (10)	0.0315 (9)	−0.0002 (9)	0.0038 (8)	−0.0015 (8)
C2	0.0682 (15)	0.0489 (13)	0.0451 (12)	0.0008 (11)	0.0017 (11)	0.0089 (10)
C3	0.0572 (14)	0.0599 (15)	0.0678 (16)	−0.0013 (12)	−0.0016 (12)	−0.0013 (12)
C4	0.0666 (15)	0.0534 (14)	0.0606 (14)	−0.0176 (12)	0.0150 (12)	−0.0203 (12)
C5	0.0842 (18)	0.0578 (14)	0.0438 (12)	−0.0181 (13)	0.0151 (12)	0.0006 (11)
C6	0.0710 (15)	0.0511 (13)	0.0377 (11)	−0.0025 (11)	0.0035 (10)	0.0070 (9)
C7	0.0402 (10)	0.0413 (10)	0.0295 (9)	−0.0032 (8)	0.0026 (7)	−0.0030 (8)
C8	0.0385 (10)	0.0495 (12)	0.0284 (9)	−0.0088 (9)	0.0018 (7)	−0.0042 (8)
C9	0.0575 (13)	0.0475 (12)	0.0365 (10)	−0.0180 (10)	−0.0030 (9)	−0.0004 (9)
C10	0.0684 (15)	0.0395 (12)	0.0606 (14)	−0.0015 (11)	−0.0082 (12)	0.0003 (10)
C11	0.0512 (13)	0.0514 (13)	0.0701 (15)	0.0085 (11)	0.0066 (11)	−0.0062 (11)
C12	0.0450 (11)	0.0494 (12)	0.0472 (11)	−0.0024 (9)	0.0133 (9)	−0.0052 (9)
C13	0.0745 (18)	0.086 (2)	0.101 (2)	−0.0270 (16)	0.0265 (16)	−0.0226 (17)
C14	0.0445 (11)	0.0740 (16)	0.0450 (12)	−0.0075 (11)	0.0133 (9)	−0.0088 (11)
C15	0.096 (2)	0.0647 (16)	0.0538 (14)	−0.0357 (15)	0.0068 (13)	0.0085 (12)
N1	0.0550 (10)	0.0458 (9)	0.0248 (7)	0.0013 (8)	0.0052 (7)	0.0017 (7)
O1	0.0795 (11)	0.0646 (10)	0.0252 (7)	−0.0021 (8)	0.0122 (7)	−0.0056 (6)
O2	0.0750 (11)	0.0496 (9)	0.0645 (10)	0.0206 (8)	0.0076 (8)	0.0036 (8)
S1	0.0589 (3)	0.0400 (3)	0.0290 (2)	0.0067 (2)	0.0089 (2)	−0.00128 (19)

C1—C6	1.389 (3)	C10—C11	1.381 (3)
C1—C2	1.391 (3)	C10—H10	0.9300
C1—S1	1.773 (2)	C11—C12	1.379 (3)
C2—C3	1.389 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.388 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.385 (4)	C13—H13C	0.9600
C4—C13	1.522 (3)	C14—H14A	0.9600
C5—C6	1.381 (3)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—C12	1.392 (3)	C15—H15B	0.9600
C7—C8	1.404 (2)	C15—H15C	0.9600
C7—N1	1.445 (2)	N1—S1	1.6288 (17)
C8—C9	1.410 (3)	N1—H1N	0.845 (9)
C8—C14	1.509 (3)	O1—S1	1.4357 (14)
C9—C10	1.398 (3)	O2—S1	1.4294 (16)
C9—C15	1.509 (3)
C6—C1—C2	119.6 (2)	C10—C11—H11	120.2
C6—C1—S1	119.42 (17)	C11—C12—C7	119.44 (19)
C2—C1—S1	121.00 (15)	C11—C12—H12	120.3
C3—C2—C1	119.8 (2)	C7—C12—H12	120.3
C3—C2—H2	120.1	C4—C13—H13A	109.5
C1—C2—H2	120.1	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	117.5 (2)	H13B—C13—H13C	109.5
C5—C4—C13	121.1 (2)	C8—C14—H14A	109.5
C3—C4—C13	121.4 (3)	C8—C14—H14B	109.5
C6—C5—C4	122.4 (2)	H14A—C14—H14B	109.5
C6—C5—H5	118.8	C8—C14—H14C	109.5
C4—C5—H5	118.8	H14A—C14—H14C	109.5
C5—C6—C1	119.3 (2)	H14B—C14—H14C	109.5
C5—C6—H6	120.3	C9—C15—H15A	109.5
C1—C6—H6	120.3	C9—C15—H15B	109.5
C12—C7—C8	122.17 (19)	H15A—C15—H15B	109.5
C12—C7—N1	119.07 (16)	C9—C15—H15C	109.5
C8—C7—N1	118.70 (17)	H15A—C15—H15C	109.5
C7—C8—C9	117.52 (18)	H15B—C15—H15C	109.5
C7—C8—C14	121.86 (19)	C7—N1—S1	121.23 (13)
C9—C8—C14	120.59 (18)	C7—N1—H1N	115.7 (15)
C10—C9—C8	119.44 (18)	S1—N1—H1N	109.4 (15)
C10—C9—C15	120.3 (2)	O2—S1—O1	120.12 (9)
C8—C9—C15	120.2 (2)	O2—S1—N1	106.14 (10)
C11—C10—C9	121.8 (2)	O1—S1—N1	106.51 (9)
C11—C10—H10	119.1	O2—S1—C1	108.09 (10)
C9—C10—H10	119.1	O1—S1—C1	107.27 (10)
C12—C11—C10	119.6 (2)	N1—S1—C1	108.23 (9)
C12—C11—H11	120.2
C6—C1—C2—C3	−0.9 (3)	C8—C9—C10—C11	−1.3 (3)
S1—C1—C2—C3	177.42 (17)	C15—C9—C10—C11	177.8 (2)
C1—C2—C3—C4	0.2 (4)	C9—C10—C11—C12	1.7 (4)
C2—C3—C4—C5	0.8 (3)	C10—C11—C12—C7	−0.4 (3)
C2—C3—C4—C13	−179.3 (2)	C8—C7—C12—C11	−1.2 (3)
C3—C4—C5—C6	−1.2 (3)	N1—C7—C12—C11	−178.47 (18)
C13—C4—C5—C6	178.8 (2)	C12—C7—N1—S1	−93.10 (19)
C4—C5—C6—C1	0.6 (3)	C8—C7—N1—S1	89.58 (19)
C2—C1—C6—C5	0.5 (3)	C7—N1—S1—O2	−163.99 (14)
S1—C1—C6—C5	−177.87 (16)	C7—N1—S1—O1	−34.88 (17)
C12—C7—C8—C9	1.6 (3)	C7—N1—S1—C1	80.18 (15)
N1—C7—C8—C9	178.83 (16)	C6—C1—S1—O2	−24.52 (19)
C12—C7—C8—C14	−176.82 (18)	C2—C1—S1—O2	157.18 (17)
N1—C7—C8—C14	0.4 (3)	C6—C1—S1—O1	−155.40 (16)
C7—C8—C9—C10	−0.3 (3)	C2—C1—S1—O1	26.30 (19)
C14—C8—C9—C10	178.10 (19)	C6—C1—S1—N1	90.03 (18)
C7—C8—C9—C15	−179.40 (18)	C2—C1—S1—N1	−88.26 (18)
C14—C8—C9—C15	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.08 (1)	2.8999 (19)	165 (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)	2.08 (1)	2.8999 (19)	165 (2)

Symmetry code: (i) .