N-(2-Methyl-phen-yl)benzene-sulfonamide.

In the title compound, C(13)H(13)NO(2)S, the conformation of the N-H bond is anti to the ortho-methyl group on the aniline ring, in contrast to the syn conformation observed with respect to the ortho-chloro group in N-(2-chloro-phen-yl)benzene-sulfonamide. The dihedral angle between the two benzene rings is 61.5 (1)°. Mol-ecules are linked into chains running along the a axis by N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gelbrich et al., 2007 ▶; Gowda et al. (2005 ▶, 2007a ▶,b ▶, 2008 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H13NO2S

M = 247.30

Orthorhombic,

a = 6.4840 (6) Å

b = 8.6124 (8) Å

c = 21.915 (2) Å

V = 1223.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 299 (2) K

0.50 × 0.50 × 0.45 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.884, T max = 0.895

4256 measured reflections

2347 independent reflections

2164 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.07

2347 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 883 Friedel pairs

Flack parameter: 0.02 (10)

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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024562/ci2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024562/ci2650Isup2.hkl

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

C13H13NO2S	F000 = 520
Mr = 247.30	Dx = 1.342 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2747 reflections
a = 6.4840 (6) Å	θ = 2.4–28.0º
b = 8.6124 (8) Å	µ = 0.25 mm−1
c = 21.915 (2) Å	T = 299 (2) K
V = 1223.8 (2) Å3	Prism, colourless
Z = 4	0.50 × 0.50 × 0.45 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2347 independent reflections
Radiation source: fine-focus sealed tube	2164 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 299(2) K	θmax = 26.4º
ω and φ scans	θmin = 3.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −7→5
Tmin = 0.884, Tmax = 0.895	k = −10→9
4256 measured reflections	l = −18→27

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.06P)2 + 0.3217P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106	(Δ/σ)max = 0.014
S = 1.08	Δρmax = 0.22 e Å−3
2347 reflections	Δρmin = −0.35 e Å−3
184 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 883 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (10)

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	0.47917 (9)	0.38178 (7)	0.43612 (2)	0.04060 (17)
O1	0.5270 (3)	0.3651 (2)	0.49979 (8)	0.0608 (5)
O2	0.6400 (3)	0.4082 (2)	0.39280 (9)	0.0589 (5)
N1	0.3623 (3)	0.2218 (2)	0.41762 (8)	0.0391 (4)
H1N	0.271 (5)	0.195 (3)	0.4409 (13)	0.047*
C1	0.2996 (3)	0.5346 (2)	0.43031 (10)	0.0362 (5)
C2	0.3264 (5)	0.6510 (3)	0.38754 (11)	0.0493 (6)
H2	0.436 (5)	0.649 (3)	0.3609 (13)	0.059*
C3	0.1819 (6)	0.7692 (3)	0.38473 (14)	0.0617 (8)
H3	0.199 (5)	0.847 (4)	0.3560 (15)	0.074*
C4	0.0157 (5)	0.7710 (3)	0.42368 (14)	0.0600 (7)
H4	−0.075 (5)	0.847 (4)	0.4198 (14)	0.072*
C5	−0.0106 (4)	0.6534 (3)	0.46522 (13)	0.0569 (7)
H5	−0.132 (5)	0.657 (4)	0.4885 (14)	0.068*
C6	0.1308 (4)	0.5347 (3)	0.46890 (11)	0.0462 (6)
H6	0.111 (5)	0.447 (3)	0.4956 (12)	0.055*
C7	0.3086 (4)	0.1940 (3)	0.35437 (10)	0.0378 (5)
C8	0.4396 (4)	0.1005 (3)	0.31992 (10)	0.0455 (5)
C9	0.3803 (6)	0.0680 (4)	0.25957 (12)	0.0601 (7)
H9	0.469 (5)	0.004 (4)	0.2348 (15)	0.072*
C10	0.2019 (6)	0.1273 (4)	0.23580 (13)	0.0689 (9)
H10	0.181 (5)	0.100 (4)	0.1956 (16)	0.083*
C11	0.0750 (6)	0.2190 (4)	0.27027 (14)	0.0668 (9)
H11	−0.059 (6)	0.265 (4)	0.2564 (17)	0.080*
C12	0.1286 (4)	0.2529 (3)	0.33042 (12)	0.0522 (6)
H12	0.043 (5)	0.318 (4)	0.3561 (14)	0.063*
C13	0.6314 (5)	0.0302 (4)	0.34651 (15)	0.0661 (8)
H13A	0.5953	−0.0343	0.3806	0.079*
H13B	0.7222	0.1114	0.3599	0.079*
H13C	0.6994	−0.0314	0.3160	0.079*

	U11	U22	U33	U12	U13	U23
S1	0.0369 (3)	0.0429 (3)	0.0419 (3)	0.0025 (2)	−0.0041 (2)	−0.0025 (2)
O1	0.0723 (13)	0.0611 (11)	0.0490 (9)	0.0122 (11)	−0.0249 (9)	−0.0039 (8)
O2	0.0390 (9)	0.0623 (12)	0.0755 (12)	−0.0041 (9)	0.0128 (9)	−0.0048 (9)
N1	0.0410 (10)	0.0420 (10)	0.0342 (9)	−0.0013 (9)	0.0041 (8)	−0.0002 (7)
C1	0.0388 (11)	0.0359 (11)	0.0338 (10)	0.0002 (9)	−0.0040 (9)	−0.0036 (9)
C2	0.0624 (16)	0.0477 (14)	0.0377 (11)	−0.0049 (12)	0.0043 (11)	0.0037 (10)
C3	0.090 (2)	0.0435 (15)	0.0517 (15)	0.0008 (15)	−0.0140 (15)	0.0098 (12)
C4	0.0627 (17)	0.0513 (14)	0.0661 (16)	0.0170 (14)	−0.0170 (15)	−0.0092 (12)
C5	0.0451 (15)	0.0594 (16)	0.0663 (16)	0.0085 (13)	0.0036 (13)	−0.0143 (12)
C6	0.0468 (14)	0.0462 (14)	0.0454 (12)	−0.0019 (12)	0.0068 (11)	−0.0003 (10)
C7	0.0427 (12)	0.0373 (11)	0.0333 (10)	−0.0047 (9)	0.0036 (9)	0.0033 (9)
C8	0.0520 (13)	0.0447 (12)	0.0398 (11)	0.0000 (11)	0.0103 (9)	0.0012 (10)
C9	0.081 (2)	0.0590 (16)	0.0408 (12)	−0.0032 (15)	0.0152 (14)	−0.0044 (12)
C10	0.095 (2)	0.075 (2)	0.0368 (12)	−0.0140 (19)	−0.0078 (15)	−0.0007 (14)
C11	0.068 (2)	0.077 (2)	0.0549 (16)	0.0008 (16)	−0.0181 (15)	0.0022 (15)
C12	0.0490 (15)	0.0592 (15)	0.0484 (13)	0.0050 (14)	−0.0045 (12)	−0.0036 (11)
C13	0.0553 (17)	0.0716 (19)	0.0713 (18)	0.0198 (16)	0.0099 (15)	−0.0114 (15)

S1—O2	1.4284 (19)	C6—H6	0.96 (3)
S1—O1	1.4365 (17)	C7—C12	1.376 (4)
S1—N1	1.624 (2)	C7—C8	1.393 (3)
S1—C1	1.762 (2)	C8—C9	1.405 (4)
N1—C7	1.449 (3)	C8—C13	1.501 (4)
N1—H1N	0.82 (3)	C9—C10	1.368 (5)
C1—C6	1.383 (3)	C9—H9	0.97 (3)
C1—C2	1.384 (3)	C10—C11	1.368 (5)
C2—C3	1.385 (4)	C10—H10	0.92 (3)
C2—H2	0.92 (3)	C11—C12	1.394 (4)
C3—C4	1.375 (5)	C11—H11	1.00 (4)
C3—H3	0.93 (3)	C12—H12	0.97 (3)
C4—C5	1.373 (4)	C13—H13A	0.96
C4—H4	0.88 (4)	C13—H13B	0.96
C5—C6	1.376 (4)	C13—H13C	0.96
C5—H5	0.94 (3)
O2—S1—O1	120.26 (13)	C1—C6—H6	118.4 (18)
O2—S1—N1	108.05 (11)	C12—C7—C8	121.6 (2)
O1—S1—N1	104.97 (11)	C12—C7—N1	120.5 (2)
O2—S1—C1	108.38 (11)	C8—C7—N1	117.8 (2)
O1—S1—C1	106.73 (11)	C7—C8—C9	117.3 (2)
N1—S1—C1	107.90 (10)	C7—C8—C13	121.9 (2)
C7—N1—S1	119.41 (15)	C9—C8—C13	120.8 (3)
C7—N1—H1N	112 (2)	C10—C9—C8	121.0 (3)
S1—N1—H1N	115 (2)	C10—C9—H9	120.4 (19)
C6—C1—C2	120.9 (2)	C8—C9—H9	118.6 (19)
C6—C1—S1	118.63 (17)	C11—C10—C9	121.0 (3)
C2—C1—S1	120.5 (2)	C11—C10—H10	126 (2)
C1—C2—C3	118.5 (3)	C9—C10—H10	113 (2)
C1—C2—H2	120.8 (19)	C10—C11—C12	119.5 (3)
C3—C2—H2	120.7 (19)	C10—C11—H11	126 (2)
C4—C3—C2	120.7 (3)	C12—C11—H11	115 (2)
C4—C3—H3	120 (2)	C7—C12—C11	119.7 (3)
C2—C3—H3	119 (2)	C7—C12—H12	118.6 (18)
C5—C4—C3	120.0 (3)	C11—C12—H12	121.8 (18)
C5—C4—H4	122 (2)	C8—C13—H13A	109.5
C3—C4—H4	118 (2)	C8—C13—H13B	109.5
C4—C5—C6	120.3 (3)	H13A—C13—H13B	109.5
C4—C5—H5	116 (2)	C8—C13—H13C	109.5
C6—C5—H5	123 (2)	H13A—C13—H13C	109.5
C5—C6—C1	119.5 (2)	H13B—C13—H13C	109.5
C5—C6—H6	122.0 (18)
O2—S1—N1—C7	−45.0 (2)	C2—C1—C6—C5	−0.9 (4)
O1—S1—N1—C7	−174.43 (18)	S1—C1—C6—C5	179.7 (2)
C1—S1—N1—C7	72.0 (2)	S1—N1—C7—C12	−84.6 (3)
O2—S1—C1—C6	−179.00 (18)	S1—N1—C7—C8	98.4 (2)
O1—S1—C1—C6	−48.1 (2)	C12—C7—C8—C9	−0.2 (4)
N1—S1—C1—C6	64.23 (19)	N1—C7—C8—C9	176.8 (2)
O2—S1—C1—C2	1.6 (2)	C12—C7—C8—C13	−177.3 (3)
O1—S1—C1—C2	132.5 (2)	N1—C7—C8—C13	−0.3 (3)
N1—S1—C1—C2	−115.2 (2)	C7—C8—C9—C10	0.6 (4)
C6—C1—C2—C3	0.9 (4)	C13—C8—C9—C10	177.7 (3)
S1—C1—C2—C3	−179.7 (2)	C8—C9—C10—C11	−0.6 (5)
C1—C2—C3—C4	0.2 (4)	C9—C10—C11—C12	0.3 (5)
C2—C3—C4—C5	−1.2 (4)	C8—C7—C12—C11	−0.1 (4)
C3—C4—C5—C6	1.2 (4)	N1—C7—C12—C11	−177.1 (3)
C4—C5—C6—C1	−0.1 (4)	C10—C11—C12—C7	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (3)	2.11 (3)	2.926 (3)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (3)	2.11 (3)	2.926 (3)	178 (3)

Symmetry code: (i) .