4-Methyl-N-phenyl-benzene-sulfonamide.

In the title compound, C(13)H(13)NO(2)S, the dihedral angle between the aromatic rings is 68.4 (1)°. In the crystal, the molecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds. The unit cell of this compound was reported previously [Oh et al. (1985 ▶). Chung. Kwa. Yong. (Chung. J. Sci.), 12, 67] but no atomic coordinates were established in the earlier study.

Related literature

For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2005 ▶, 2009 ▶ ▶); Gowda, Foro, Nirmala, Terao & Fuess (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H13NO2S

M = 247.30

Monoclinic,

a = 8.770 (2) Å

b = 9.768 (2) Å

c = 16.234 (5) Å

β = 113.200 (2)°

V = 1278.2 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.17 mm−1

T = 299 K

0.55 × 0.50 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.336, T max = 0.420

3091 measured reflections

2278 independent reflections

2041 reflections with I > 2σ(I)

R int = 0.096

3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.217

S = 1.10

2278 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536809016377/bq2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016377/bq2138Isup2.hkl

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

C13H13NO2S	F(000) = 520
Mr = 247.30	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.770 (2) Å	θ = 5.4–20.7°
b = 9.768 (2) Å	µ = 2.17 mm−1
c = 16.234 (5) Å	T = 299 K
β = 113.200 (2)°	Prism, colourless
V = 1278.2 (6) Å3	0.55 × 0.50 × 0.40 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.096
graphite	θmax = 66.9°, θmin = 5.4°
ω/2θ scans	h = −3→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
Tmin = 0.336, Tmax = 0.420	l = −19→19
3091 measured reflections	3 standard reflections every 120 min
2278 independent reflections	intensity decay: 2.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.217	w = 1/[σ2(Fo2) + (0.1256P)2 + 0.4489P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.023
2278 reflections	Δρmax = 0.47 e Å−3
159 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: (SHELXL97; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (5)

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	0.3623 (4)	0.2024 (3)	0.4713 (2)	0.0641 (7)
C2	0.2930 (5)	0.0780 (4)	0.4369 (2)	0.0810 (9)
H2	0.2768	0.0535	0.3787	0.097*
C3	0.2480 (5)	−0.0098 (4)	0.4897 (3)	0.0929 (11)
H3	0.2037	−0.0949	0.4670	0.112*
C4	0.2669 (4)	0.0254 (4)	0.5752 (3)	0.0866 (11)
C5	0.3360 (5)	0.1527 (5)	0.6073 (3)	0.0881 (11)
H5	0.3495	0.1790	0.6648	0.106*
C6	0.3838 (4)	0.2390 (4)	0.5571 (2)	0.0799 (9)
H6	0.4313	0.3230	0.5804	0.096*
C7	0.1172 (4)	0.4284 (3)	0.3472 (2)	0.0708 (8)
C8	0.0374 (5)	0.3408 (4)	0.2771 (3)	0.0855 (10)
H8	0.0972	0.2892	0.2519	0.103*
C9	−0.1321 (5)	0.3311 (5)	0.2450 (3)	0.0982 (13)
H9	−0.1867	0.2712	0.1981	0.118*
C10	−0.2223 (5)	0.4065 (6)	0.2800 (4)	0.1095 (16)
H10	−0.3372	0.3987	0.2570	0.131*
C11	−0.1428 (6)	0.4932 (6)	0.3488 (4)	0.1133 (16)
H11	−0.2042	0.5457	0.3725	0.136*
C12	0.0292 (5)	0.5048 (4)	0.3844 (3)	0.0899 (11)
H12	0.0833	0.5631	0.4324	0.108*
C13	0.2197 (7)	−0.0689 (6)	0.6336 (4)	0.1236 (18)
H13A	0.1824	−0.1544	0.6032	0.148*
H13B	0.1322	−0.0283	0.6468	0.148*
H13C	0.3142	−0.0845	0.6884	0.148*
N1	0.2939 (3)	0.4457 (3)	0.3838 (2)	0.0762 (8)
H1N	0.318 (5)	0.497 (5)	0.423 (3)	0.091*
O1	0.5798 (3)	0.3739 (3)	0.45932 (19)	0.0863 (8)
O2	0.4014 (3)	0.2496 (3)	0.32444 (16)	0.0858 (8)
S1	0.42133 (9)	0.31592 (8)	0.40573 (5)	0.0689 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0670 (15)	0.0712 (17)	0.0583 (16)	0.0062 (12)	0.0292 (13)	−0.0007 (13)
C2	0.104 (2)	0.077 (2)	0.071 (2)	−0.0127 (17)	0.0435 (18)	−0.0128 (16)
C3	0.111 (3)	0.077 (2)	0.103 (3)	−0.0077 (19)	0.055 (2)	0.001 (2)
C4	0.091 (2)	0.095 (2)	0.091 (2)	0.029 (2)	0.054 (2)	0.029 (2)
C5	0.103 (2)	0.106 (3)	0.066 (2)	0.017 (2)	0.0442 (18)	0.0030 (19)
C6	0.095 (2)	0.086 (2)	0.0664 (19)	0.0000 (17)	0.0399 (17)	−0.0132 (16)
C7	0.0718 (17)	0.0718 (18)	0.0711 (18)	−0.0004 (13)	0.0305 (14)	0.0198 (14)
C8	0.089 (2)	0.091 (2)	0.076 (2)	−0.0102 (18)	0.0330 (18)	0.0057 (18)
C9	0.084 (2)	0.106 (3)	0.090 (3)	−0.013 (2)	0.019 (2)	0.019 (2)
C10	0.079 (2)	0.121 (4)	0.114 (4)	−0.003 (2)	0.023 (2)	0.038 (3)
C11	0.094 (3)	0.127 (4)	0.128 (4)	0.030 (3)	0.054 (3)	0.028 (3)
C12	0.090 (2)	0.088 (2)	0.095 (3)	0.0093 (18)	0.0404 (19)	0.008 (2)
C13	0.143 (4)	0.120 (4)	0.140 (4)	0.033 (3)	0.090 (3)	0.052 (3)
N1	0.0754 (16)	0.0734 (17)	0.0824 (19)	−0.0075 (12)	0.0341 (14)	−0.0006 (13)
O1	0.0727 (13)	0.0901 (16)	0.1026 (18)	−0.0101 (11)	0.0414 (12)	−0.0152 (14)
O2	0.1054 (17)	0.0989 (18)	0.0709 (14)	−0.0013 (14)	0.0541 (13)	−0.0068 (12)
S1	0.0721 (6)	0.0749 (6)	0.0691 (6)	−0.0036 (3)	0.0379 (4)	−0.0048 (3)

C1—C2	1.374 (5)	C8—H8	0.9300
C1—C6	1.378 (4)	C9—C10	1.358 (7)
C1—S1	1.750 (3)	C9—H9	0.9300
C2—C3	1.375 (5)	C10—C11	1.355 (8)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.375 (6)	C11—C12	1.391 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.392 (6)	C12—H12	0.9300
C4—C13	1.492 (5)	C13—H13A	0.9600
C5—C6	1.349 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.633 (3)
C7—C12	1.373 (5)	N1—H1N	0.77 (4)
C7—C8	1.375 (5)	O1—S1	1.434 (2)
C7—N1	1.434 (4)	O2—S1	1.418 (2)
C8—C9	1.371 (5)
C2—C1—C6	120.1 (3)	C8—C9—H9	119.1
C2—C1—S1	120.2 (2)	C11—C10—C9	119.2 (4)
C6—C1—S1	119.7 (3)	C11—C10—H10	120.4
C1—C2—C3	119.2 (3)	C9—C10—H10	120.4
C1—C2—H2	120.4	C10—C11—C12	121.0 (5)
C3—C2—H2	120.4	C10—C11—H11	119.5
C2—C3—C4	121.5 (4)	C12—C11—H11	119.5
C2—C3—H3	119.2	C7—C12—C11	118.6 (4)
C4—C3—H3	119.2	C7—C12—H12	120.7
C3—C4—C5	117.6 (3)	C11—C12—H12	120.7
C3—C4—C13	122.3 (5)	C4—C13—H13A	109.5
C5—C4—C13	120.1 (4)	C4—C13—H13B	109.5
C6—C5—C4	121.7 (3)	H13A—C13—H13B	109.5
C6—C5—H5	119.2	C4—C13—H13C	109.5
C4—C5—H5	119.2	H13A—C13—H13C	109.5
C5—C6—C1	119.9 (4)	H13B—C13—H13C	109.5
C5—C6—H6	120.1	C7—N1—S1	122.3 (2)
C1—C6—H6	120.1	C7—N1—H1N	109 (3)
C12—C7—C8	120.7 (3)	S1—N1—H1N	113 (3)
C12—C7—N1	117.2 (3)	O2—S1—O1	118.69 (15)
C8—C7—N1	122.0 (3)	O2—S1—N1	109.20 (17)
C9—C8—C7	118.7 (4)	O1—S1—N1	104.00 (16)
C9—C8—H8	120.7	O2—S1—C1	108.57 (15)
C7—C8—H8	120.7	O1—S1—C1	109.23 (16)
C10—C9—C8	121.8 (5)	N1—S1—C1	106.47 (14)
C10—C9—H9	119.1
C6—C1—C2—C3	−0.9 (5)	C8—C7—C12—C11	−0.9 (6)
S1—C1—C2—C3	179.8 (3)	N1—C7—C12—C11	178.3 (4)
C1—C2—C3—C4	1.6 (6)	C10—C11—C12—C7	1.3 (7)
C2—C3—C4—C5	−1.0 (6)	C12—C7—N1—S1	135.5 (3)
C2—C3—C4—C13	−179.6 (4)	C8—C7—N1—S1	−45.3 (4)
C3—C4—C5—C6	−0.3 (5)	C7—N1—S1—O2	65.5 (3)
C13—C4—C5—C6	178.3 (4)	C7—N1—S1—O1	−166.9 (3)
C4—C5—C6—C1	1.0 (6)	C7—N1—S1—C1	−51.6 (3)
C2—C1—C6—C5	−0.3 (5)	C2—C1—S1—O2	−6.3 (3)
S1—C1—C6—C5	178.9 (3)	C6—C1—S1—O2	174.5 (2)
C12—C7—C8—C9	−0.1 (5)	C2—C1—S1—O1	−137.1 (3)
N1—C7—C8—C9	−179.2 (3)	C6—C1—S1—O1	43.7 (3)
C7—C8—C9—C10	0.7 (6)	C2—C1—S1—N1	111.2 (3)
C8—C9—C10—C11	−0.4 (7)	C6—C1—S1—N1	−68.0 (3)
C9—C10—C11—C12	−0.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.77 (4)	2.17 (5)	2.932 (4)	172 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.77 (4)	2.17 (5)	2.932 (4)	172 (4)

Symmetry code: (i) .