4-Methyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(15)NO(2)S, the two aromatic rings enclose a dihedral angle of 70.53 (10)°. A weak intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Deng & Mani (2006 ▶). For the biological activity of sulfonamides, see: Pandya et al. (2003 ▶); Supuran & Scozzafava (2000 ▶). For the effects of substituents on the crystal structures of and bond lengths in aryl sulfonamides, see: Sharif et al. (2010 ▶); Gowda et al. (2008 ▶, 2009 ▶, 2010 ▶); Nirmala et al. (2009a ▶,b ▶)·For graph-set notation, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.34

Triclinic,

a = 8.6419 (8) Å

b = 8.8016 (8) Å

c = 9.2509 (7) Å

α = 88.187 (4)°

β = 77.010 (4)°

γ = 74.812 (4)°

V = 661.41 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.28 × 0.17 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

11831 measured reflections

3259 independent reflections

2323 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.01

3259 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008329/bt5205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008329/bt5205Isup2.hkl

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

C14H15NO2S	Z = 2
Mr = 261.34	F(000) = 276
Triclinic, P1	Dx = 1.312 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6419 (8) Å	Cell parameters from 3233 reflections
b = 8.8016 (8) Å	θ = 2.4–25.6°
c = 9.2509 (7) Å	µ = 0.24 mm−1
α = 88.187 (4)°	T = 296 K
β = 77.010 (4)°	Rod like, light brown
γ = 74.812 (4)°	0.28 × 0.17 × 0.08 mm
V = 661.41 (10) Å3

Bruker APEXII CCD diffractometer	2323 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.038
graphite	θmax = 28.4°, θmin = 3.4°
φ and ω scans	h = −11→11
11831 measured reflections	k = −11→11
3259 independent reflections	l = −11→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0376P] where P = (Fo2 + 2Fc2)/3
3259 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.18536 (5)	0.76639 (5)	0.92202 (4)	0.0448 (2)
O1	0.34628 (15)	0.66385 (16)	0.90275 (15)	0.0579 (4)
O2	0.10049 (15)	0.83328 (15)	1.06641 (12)	0.0537 (4)
N1	0.1950 (2)	0.91823 (19)	0.81866 (16)	0.0471 (5)
C1	0.4564 (3)	0.9071 (3)	0.1918 (2)	0.0860 (9)
C2	0.3869 (3)	0.9072 (3)	0.3562 (2)	0.0589 (7)
C3	0.4706 (3)	0.8100 (3)	0.4474 (2)	0.0635 (7)
C4	0.4115 (2)	0.8091 (2)	0.5988 (2)	0.0570 (7)
C5	0.2605 (2)	0.9077 (2)	0.66194 (18)	0.0423 (5)
C6	0.1743 (2)	1.0070 (2)	0.5727 (2)	0.0559 (6)
C7	0.2379 (3)	1.0074 (3)	0.4220 (2)	0.0661 (8)
C8	0.0609 (2)	0.66738 (19)	0.85725 (18)	0.0428 (5)
C9	0.1315 (2)	0.5487 (2)	0.7513 (2)	0.0608 (7)
C10	0.0316 (3)	0.4755 (2)	0.6978 (2)	0.0668 (8)
C11	−0.1361 (2)	0.5162 (2)	0.7502 (2)	0.0526 (6)
C12	−0.2036 (2)	0.6345 (2)	0.8566 (2)	0.0597 (7)
C13	−0.1067 (2)	0.7097 (2)	0.9103 (2)	0.0566 (7)
C14	−0.2439 (3)	0.4335 (3)	0.6927 (2)	0.0702 (8)
H1	0.118 (3)	0.994 (3)	0.843 (2)	0.068 (7)*
H1A	0.52890	0.97510	0.17190	0.1290*
H1B	0.36830	0.94410	0.14160	0.1290*
H1C	0.51650	0.80190	0.15690	0.1290*
H3	0.57180	0.74160	0.40540	0.0760*
H4	0.47290	0.74260	0.65750	0.0680*
H6	0.07230	1.07450	0.61420	0.0670*
H7	0.17880	1.07680	0.36360	0.0790*
H9	0.24500	0.51800	0.71600	0.0730*
H10	0.07920	0.39670	0.62450	0.0800*
H12	−0.31690	0.66430	0.89310	0.0720*
H13	−0.15450	0.78950	0.98270	0.0680*
H14A	−0.27990	0.48930	0.61030	0.1050*
H14B	−0.33800	0.43100	0.77020	0.1050*
H14C	−0.18250	0.32780	0.66110	0.1050*

	U11	U22	U33	U12	U13	U23
S1	0.0441 (3)	0.0466 (3)	0.0429 (2)	−0.0104 (2)	−0.0093 (2)	−0.0033 (2)
O1	0.0451 (7)	0.0608 (8)	0.0641 (8)	−0.0050 (6)	−0.0149 (6)	−0.0001 (6)
O2	0.0579 (8)	0.0586 (8)	0.0416 (6)	−0.0118 (6)	−0.0084 (5)	−0.0055 (6)
N1	0.0467 (9)	0.0452 (9)	0.0461 (8)	−0.0127 (8)	−0.0018 (6)	−0.0058 (7)
C1	0.0891 (17)	0.131 (2)	0.0475 (11)	−0.0617 (17)	0.0057 (10)	−0.0124 (12)
C2	0.0595 (13)	0.0780 (14)	0.0495 (10)	−0.0430 (11)	−0.0023 (9)	−0.0089 (10)
C3	0.0528 (12)	0.0689 (13)	0.0619 (12)	−0.0190 (10)	0.0074 (9)	−0.0175 (10)
C4	0.0472 (11)	0.0590 (12)	0.0575 (11)	−0.0080 (9)	−0.0032 (8)	−0.0046 (9)
C5	0.0404 (9)	0.0443 (9)	0.0449 (9)	−0.0197 (8)	−0.0036 (7)	−0.0069 (7)
C6	0.0432 (10)	0.0656 (12)	0.0558 (11)	−0.0151 (9)	−0.0042 (8)	0.0038 (9)
C7	0.0588 (13)	0.0898 (16)	0.0566 (11)	−0.0317 (12)	−0.0141 (9)	0.0142 (11)
C8	0.0452 (10)	0.0391 (9)	0.0426 (8)	−0.0108 (7)	−0.0070 (7)	0.0009 (7)
C9	0.0454 (11)	0.0571 (12)	0.0748 (13)	−0.0116 (9)	−0.0022 (9)	−0.0200 (10)
C10	0.0683 (14)	0.0542 (12)	0.0765 (14)	−0.0164 (11)	−0.0098 (11)	−0.0226 (10)
C11	0.0611 (12)	0.0487 (10)	0.0549 (10)	−0.0222 (9)	−0.0189 (9)	0.0085 (8)
C12	0.0452 (11)	0.0654 (13)	0.0676 (12)	−0.0160 (10)	−0.0080 (9)	−0.0067 (10)
C13	0.0465 (11)	0.0610 (12)	0.0581 (11)	−0.0120 (9)	−0.0032 (8)	−0.0160 (9)
C14	0.0783 (15)	0.0678 (14)	0.0790 (14)	−0.0320 (12)	−0.0324 (12)	0.0043 (11)

S1—O1	1.4217 (14)	C11—C14	1.511 (3)
S1—O2	1.4324 (12)	C11—C12	1.372 (2)
S1—N1	1.6276 (16)	C12—C13	1.373 (3)
S1—C8	1.7576 (18)	C1—H1A	0.9600
N1—C5	1.429 (2)	C1—H1B	0.9600
N1—H1	0.81 (3)	C1—H1C	0.9600
C1—C2	1.504 (3)	C3—H3	0.9300
C2—C7	1.376 (4)	C4—H4	0.9300
C2—C3	1.368 (3)	C6—H6	0.9300
C3—C4	1.379 (3)	C7—H7	0.9300
C4—C5	1.376 (3)	C9—H9	0.9300
C5—C6	1.375 (2)	C10—H10	0.9300
C6—C7	1.379 (3)	C12—H12	0.9300
C8—C13	1.374 (3)	C13—H13	0.9300
C8—C9	1.373 (2)	C14—H14A	0.9600
C9—C10	1.382 (3)	C14—H14B	0.9600
C10—C11	1.374 (3)	C14—H14C	0.9600
S1···H4	3.0400	H1···O2i	2.11 (3)
O1···C4	3.049 (2)	H1A···N1iv	2.8000
O2···N1i	2.904 (2)	H1A···C5iv	3.0100
O2···C14ii	3.377 (3)	H1B···H7	2.4300
O1···H4	2.4500	H1C···H3	2.4700
O1···H9	2.6100	H3···H1C	2.4700
O1···H12iii	2.8900	H3···H9vii	2.5400
O2···H13	2.6100	H4···S1	3.0400
O2···H1i	2.11 (3)	H4···O1	2.4500
N1···O2i	2.904 (2)	H6···H1	2.3000
N1···H1Aiv	2.8000	H6···C7v	3.0400
C2···C4iv	3.481 (3)	H7···H1B	2.4300
C4···O1	3.049 (2)	H9···O1	2.6100
C4···C2iv	3.481 (3)	H9···H3vii	2.5400
C6···C6v	3.595 (3)	H10···H14C	2.4400
C6···C7v	3.587 (3)	H12···O1viii	2.8900
C7···C6v	3.587 (3)	H12···H14B	2.4500
C14···O2ii	3.377 (3)	H13···O2	2.6100
C2···H14Cvi	3.0800	H14B···H12	2.4500
C5···H1Aiv	3.0100	H14C···H10	2.4400
C7···H6v	3.0400	H14C···C2vi	3.0800
H1···H6	2.3000
O1—S1—O2	119.28 (8)	C2—C1—H1A	109.00
O1—S1—N1	108.52 (9)	C2—C1—H1B	110.00
O1—S1—C8	108.38 (8)	C2—C1—H1C	109.00
O2—S1—N1	104.26 (8)	H1A—C1—H1B	109.00
O2—S1—C8	108.41 (8)	H1A—C1—H1C	109.00
N1—S1—C8	107.41 (8)	H1B—C1—H1C	109.00
S1—N1—C5	123.93 (13)	C2—C3—H3	118.00
C5—N1—H1	112.3 (13)	C4—C3—H3	119.00
S1—N1—H1	114.3 (16)	C3—C4—H4	120.00
C1—C2—C7	121.5 (2)	C5—C4—H4	120.00
C1—C2—C3	121.5 (2)	C5—C6—H6	120.00
C3—C2—C7	117.01 (18)	C7—C6—H6	120.00
C2—C3—C4	122.9 (2)	C2—C7—H7	119.00
C3—C4—C5	119.16 (18)	C6—C7—H7	119.00
C4—C5—C6	119.03 (16)	C8—C9—H9	120.00
N1—C5—C6	118.64 (16)	C10—C9—H9	120.00
N1—C5—C4	122.18 (16)	C9—C10—H10	119.00
C5—C6—C7	120.51 (18)	C11—C10—H10	119.00
C2—C7—C6	121.4 (2)	C11—C12—H12	119.00
C9—C8—C13	119.86 (17)	C13—C12—H12	119.00
S1—C8—C9	119.76 (14)	C8—C13—H13	120.00
S1—C8—C13	120.37 (13)	C12—C13—H13	120.00
C8—C9—C10	119.12 (17)	C11—C14—H14A	109.00
C9—C10—C11	121.65 (16)	C11—C14—H14B	109.00
C10—C11—C14	121.20 (17)	C11—C14—H14C	110.00
C10—C11—C12	118.13 (17)	H14A—C14—H14B	109.00
C12—C11—C14	120.68 (17)	H14A—C14—H14C	109.00
C11—C12—C13	121.15 (17)	H14B—C14—H14C	109.00
C8—C13—C12	120.09 (16)
O1—S1—N1—C5	56.26 (18)	C3—C4—C5—C6	−1.4 (3)
O2—S1—N1—C5	−175.62 (16)	C3—C4—C5—N1	−177.08 (19)
C8—S1—N1—C5	−60.71 (18)	C4—C5—C6—C7	0.3 (3)
O1—S1—C8—C13	155.34 (14)	N1—C5—C6—C7	176.04 (19)
O2—S1—C8—C13	24.51 (16)	C5—C6—C7—C2	1.3 (3)
N1—S1—C8—C13	−87.60 (15)	S1—C8—C9—C10	−177.84 (13)
O2—S1—C8—C9	−156.51 (14)	C13—C8—C9—C10	1.2 (3)
N1—S1—C8—C9	91.38 (15)	S1—C8—C13—C12	178.40 (14)
O1—S1—C8—C9	−25.69 (16)	C9—C8—C13—C12	−0.6 (3)
S1—N1—C5—C6	134.31 (16)	C8—C9—C10—C11	−1.4 (3)
S1—N1—C5—C4	−50.0 (2)	C9—C10—C11—C12	1.0 (3)
C3—C2—C7—C6	−1.5 (4)	C9—C10—C11—C14	−178.98 (17)
C1—C2—C7—C6	179.9 (2)	C10—C11—C12—C13	−0.5 (3)
C7—C2—C3—C4	0.2 (4)	C14—C11—C12—C13	179.57 (17)
C1—C2—C3—C4	178.9 (2)	C11—C12—C13—C8	0.2 (3)
C2—C3—C4—C5	1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.81 (3)	2.11 (3)	2.904 (2)	170 (2)
C4—H4···O1	0.93	2.45	3.049 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.81 (3)	2.11 (3)	2.904 (2)	170 (2)
C4—H4⋯O1	0.93	2.45	3.049 (2)	122

Symmetry code: (i) .