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

The asymmetric unit of the title compound, C(13)H(13)NO(2)S, contains two independent mol-ecules. The dihedral angles between the aromatic rings in the two mol-ecules are 78.0 (1) and 74.0 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds pack the mol-ecules into a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008 ▶, 2010 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H13NO2S

M = 247.30

Monoclinic,

a = 10.8963 (7) Å

b = 9.6981 (7) Å

c = 24.089 (2) Å

β = 101.335 (6)°

V = 2495.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 299 K

0.48 × 0.36 × 0.36 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.890, T max = 0.916

11057 measured reflections

5102 independent reflections

3835 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.07

5102 reflections

317 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.44 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/S1600536810002278/bt5173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002278/bt5173Isup2.hkl

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

C13H13NO2S	F(000) = 1040
Mr = 247.30	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3814 reflections
a = 10.8963 (7) Å	θ = 2.6–27.8°
b = 9.6981 (7) Å	µ = 0.25 mm−1
c = 24.089 (2) Å	T = 299 K
β = 101.335 (6)°	Prism, colourless
V = 2495.9 (3) Å3	0.48 × 0.36 × 0.36 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	5102 independent reflections
Radiation source: fine-focus sealed tube	3835 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→6
Tmin = 0.890, Tmax = 0.916	k = −8→12
11057 measured reflections	l = −30→29

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1533P] where P = (Fo2 + 2Fc2)/3
5102 reflections	(Δ/σ)max = 0.022
317 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.44 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	0.49646 (15)	0.23424 (19)	0.34166 (7)	0.0352 (4)
C2	0.54145 (19)	0.1458 (2)	0.38595 (8)	0.0540 (5)
H2	0.5706	0.0585	0.3792	0.065*
C3	0.5422 (2)	0.1902 (3)	0.44079 (9)	0.0743 (7)
H3	0.5714	0.1317	0.4711	0.089*
C4	0.5009 (2)	0.3177 (3)	0.45059 (10)	0.0729 (7)
H4	0.5017	0.3455	0.4876	0.087*
C5	0.4576 (2)	0.4073 (3)	0.40631 (10)	0.0637 (6)
H5	0.4304	0.4952	0.4135	0.076*
C6	0.45504 (17)	0.3650 (2)	0.35136 (8)	0.0473 (5)
H6	0.4257	0.4239	0.3212	0.057*
C7	0.72265 (15)	0.26027 (18)	0.26558 (7)	0.0345 (4)
C8	0.78605 (17)	0.38435 (19)	0.27057 (8)	0.0437 (4)
H8	0.7424	0.4664	0.2618	0.052*
C9	0.91509 (18)	0.3864 (2)	0.28866 (9)	0.0519 (5)
H9	0.9569	0.4705	0.2916	0.062*
C10	0.98274 (17)	0.2673 (2)	0.30237 (8)	0.0483 (5)
C11	0.91807 (17)	0.1439 (2)	0.29706 (8)	0.0492 (5)
H11	0.9621	0.0621	0.3061	0.059*
C12	0.78924 (17)	0.1386 (2)	0.27865 (8)	0.0445 (4)
H12	0.7478	0.0543	0.2751	0.053*
C13	1.1240 (2)	0.2704 (3)	0.32199 (12)	0.0782 (8)
H13A	1.1543	0.3620	0.3178	0.094*
H13B	1.1619	0.2076	0.2995	0.094*
H13C	1.1452	0.2435	0.3611	0.094*
N1	0.59074 (13)	0.26099 (17)	0.24393 (6)	0.0380 (4)
H1N	0.5641 (19)	0.3419 (13)	0.2338 (9)	0.061 (7)*
O1	0.36880 (11)	0.21729 (15)	0.23898 (5)	0.0483 (3)
O2	0.52235 (12)	0.03473 (13)	0.27441 (6)	0.0484 (3)
S1	0.48854 (4)	0.17773 (5)	0.271806 (17)	0.03439 (13)
C14	0.24474 (16)	0.1155 (2)	0.04914 (8)	0.0433 (4)
C15	0.23588 (19)	0.0133 (2)	0.08819 (10)	0.0539 (5)
H15	0.2661	0.0292	0.1265	0.065*
C16	0.1824 (2)	−0.1121 (3)	0.07043 (13)	0.0746 (7)
H16	0.1760	−0.1812	0.0965	0.089*
C17	0.1387 (3)	−0.1331 (3)	0.01356 (16)	0.0934 (10)
H17	0.1026	−0.2175	0.0013	0.112*
C18	0.1469 (3)	−0.0333 (4)	−0.02519 (13)	0.0927 (10)
H18	0.1169	−0.0504	−0.0634	0.111*
C19	0.1998 (2)	0.0942 (3)	−0.00817 (9)	0.0691 (7)
H19	0.2050	0.1631	−0.0345	0.083*
C20	0.12459 (15)	0.34730 (18)	0.11770 (7)	0.0355 (4)
C21	0.05945 (18)	0.2725 (2)	0.15145 (8)	0.0440 (4)
H21	0.1015	0.2087	0.1772	0.053*
C22	−0.06751 (19)	0.2922 (2)	0.14710 (9)	0.0521 (5)
H22	−0.1096	0.2421	0.1704	0.063*
C23	−0.13356 (18)	0.3848 (3)	0.10883 (8)	0.0544 (6)
C24	−0.06742 (18)	0.4595 (2)	0.07557 (8)	0.0558 (6)
H24	−0.1099	0.5226	0.0497	0.067*
C25	0.06092 (18)	0.4430 (2)	0.07982 (7)	0.0469 (5)
H25	0.1037	0.4955	0.0575	0.056*
C26	−0.2728 (2)	0.4058 (4)	0.10399 (11)	0.0918 (10)
H26A	−0.2892	0.4368	0.1397	0.110*
H26B	−0.3157	0.3203	0.0938	0.110*
H26C	−0.3019	0.4738	0.0755	0.110*
N2	0.25663 (14)	0.32896 (17)	0.12379 (6)	0.0404 (4)
H2N	0.2978 (16)	0.2947 (19)	0.1543 (6)	0.047 (6)*
O3	0.44699 (12)	0.24737 (16)	0.09618 (7)	0.0607 (4)
O4	0.28964 (14)	0.36865 (16)	0.02590 (6)	0.0614 (4)
S2	0.31882 (4)	0.27343 (5)	0.07160 (2)	0.04299 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0322 (9)	0.0384 (10)	0.0348 (9)	−0.0071 (7)	0.0058 (7)	0.0000 (7)
C2	0.0650 (13)	0.0520 (13)	0.0431 (11)	−0.0009 (10)	0.0057 (9)	0.0080 (9)
C3	0.0945 (19)	0.087 (2)	0.0382 (12)	−0.0135 (15)	0.0046 (12)	0.0091 (12)
C4	0.0800 (17)	0.099 (2)	0.0450 (12)	−0.0294 (15)	0.0256 (12)	−0.0179 (14)
C5	0.0673 (14)	0.0626 (15)	0.0674 (15)	−0.0120 (11)	0.0287 (12)	−0.0233 (13)
C6	0.0494 (11)	0.0438 (12)	0.0506 (11)	−0.0020 (9)	0.0143 (9)	−0.0026 (9)
C7	0.0341 (9)	0.0401 (10)	0.0308 (8)	0.0032 (7)	0.0098 (7)	0.0025 (7)
C8	0.0412 (10)	0.0343 (10)	0.0576 (11)	0.0038 (8)	0.0142 (8)	−0.0011 (9)
C9	0.0435 (11)	0.0485 (13)	0.0661 (13)	−0.0092 (9)	0.0169 (9)	−0.0090 (10)
C10	0.0345 (10)	0.0672 (14)	0.0444 (11)	0.0020 (9)	0.0107 (8)	0.0004 (10)
C11	0.0393 (10)	0.0540 (13)	0.0551 (12)	0.0137 (9)	0.0116 (9)	0.0133 (10)
C12	0.0402 (10)	0.0388 (10)	0.0551 (11)	0.0037 (8)	0.0110 (8)	0.0081 (9)
C13	0.0382 (12)	0.110 (2)	0.0846 (18)	−0.0009 (13)	0.0089 (11)	−0.0004 (16)
N1	0.0324 (8)	0.0403 (9)	0.0407 (8)	0.0033 (7)	0.0060 (6)	0.0086 (7)
O1	0.0315 (7)	0.0660 (9)	0.0430 (7)	−0.0024 (6)	−0.0033 (5)	0.0012 (6)
O2	0.0528 (8)	0.0319 (7)	0.0592 (8)	−0.0058 (6)	0.0080 (6)	−0.0083 (6)
S1	0.0319 (2)	0.0350 (3)	0.0343 (2)	−0.00365 (18)	0.00181 (16)	−0.00231 (18)
C14	0.0343 (9)	0.0523 (12)	0.0441 (10)	0.0007 (8)	0.0102 (8)	−0.0094 (9)
C15	0.0524 (12)	0.0514 (13)	0.0601 (13)	−0.0001 (10)	0.0164 (10)	−0.0089 (10)
C16	0.0732 (16)	0.0505 (15)	0.105 (2)	−0.0068 (12)	0.0305 (15)	−0.0141 (14)
C17	0.084 (2)	0.076 (2)	0.126 (3)	−0.0238 (16)	0.0340 (19)	−0.051 (2)
C18	0.090 (2)	0.109 (3)	0.0741 (18)	−0.0173 (18)	0.0047 (15)	−0.0492 (18)
C19	0.0675 (15)	0.0919 (19)	0.0462 (12)	−0.0078 (13)	0.0070 (11)	−0.0188 (12)
C20	0.0378 (9)	0.0373 (10)	0.0299 (8)	0.0011 (7)	0.0030 (7)	−0.0072 (7)
C21	0.0495 (11)	0.0420 (11)	0.0397 (10)	−0.0007 (9)	0.0070 (8)	0.0009 (8)
C22	0.0523 (12)	0.0597 (14)	0.0473 (11)	−0.0102 (10)	0.0170 (9)	−0.0080 (10)
C23	0.0390 (10)	0.0812 (16)	0.0406 (10)	0.0004 (10)	0.0017 (8)	−0.0185 (10)
C24	0.0503 (12)	0.0785 (16)	0.0351 (10)	0.0199 (11)	−0.0003 (9)	0.0012 (10)
C25	0.0512 (11)	0.0550 (13)	0.0353 (9)	0.0064 (9)	0.0105 (8)	0.0042 (9)
C26	0.0420 (13)	0.156 (3)	0.0749 (17)	0.0045 (15)	0.0056 (12)	−0.0146 (18)
N2	0.0392 (8)	0.0470 (10)	0.0324 (8)	0.0027 (7)	0.0007 (6)	−0.0040 (7)
O3	0.0317 (7)	0.0740 (11)	0.0751 (10)	−0.0028 (6)	0.0074 (7)	−0.0085 (8)
O4	0.0740 (10)	0.0628 (10)	0.0528 (8)	0.0055 (8)	0.0254 (7)	0.0143 (7)
S2	0.0366 (3)	0.0491 (3)	0.0442 (3)	−0.0012 (2)	0.01009 (19)	−0.0016 (2)

C1—C6	1.381 (3)	C14—C15	1.383 (3)
C1—C2	1.382 (2)	C14—C19	1.386 (3)
C1—S1	1.7556 (17)	C14—S2	1.766 (2)
C2—C3	1.388 (3)	C15—C16	1.380 (3)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.352 (4)	C16—C17	1.375 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.385 (3)	C17—C18	1.360 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.381 (3)	C18—C19	1.391 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.381 (3)	C20—C21	1.385 (3)
C7—C12	1.389 (2)	C20—C25	1.388 (2)
C7—N1	1.429 (2)	C20—N2	1.428 (2)
C8—C9	1.388 (2)	C21—C22	1.380 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.375 (3)	C22—C23	1.383 (3)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.382 (3)	C23—C24	1.383 (3)
C10—C13	1.519 (3)	C23—C26	1.512 (3)
C11—C12	1.388 (2)	C24—C25	1.391 (3)
C11—H11	0.9300	C24—H24	0.9300
C12—H12	0.9300	C25—H25	0.9300
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600
N1—S1	1.6239 (16)	N2—S2	1.6325 (15)
N1—H1N	0.855 (9)	N2—H2N	0.850 (9)
O1—S1	1.4384 (12)	O3—S2	1.4282 (13)
O2—S1	1.4331 (13)	O4—S2	1.4240 (14)
C6—C1—C2	121.15 (18)	C15—C14—C19	120.8 (2)
C6—C1—S1	119.52 (14)	C15—C14—S2	120.13 (15)
C2—C1—S1	119.31 (15)	C19—C14—S2	119.01 (18)
C1—C2—C3	118.5 (2)	C16—C15—C14	120.2 (2)
C1—C2—H2	120.7	C16—C15—H15	119.9
C3—C2—H2	120.7	C14—C15—H15	119.9
C4—C3—C2	120.6 (2)	C17—C16—C15	118.8 (3)
C4—C3—H3	119.7	C17—C16—H16	120.6
C2—C3—H3	119.7	C15—C16—H16	120.6
C3—C4—C5	121.0 (2)	C18—C17—C16	121.4 (3)
C3—C4—H4	119.5	C18—C17—H17	119.3
C5—C4—H4	119.5	C16—C17—H17	119.3
C6—C5—C4	119.4 (2)	C17—C18—C19	120.6 (3)
C6—C5—H5	120.3	C17—C18—H18	119.7
C4—C5—H5	120.3	C19—C18—H18	119.7
C1—C6—C5	119.3 (2)	C14—C19—C18	118.1 (3)
C1—C6—H6	120.3	C14—C19—H19	121.0
C5—C6—H6	120.3	C18—C19—H19	121.0
C8—C7—C12	119.38 (16)	C21—C20—C25	119.24 (17)
C8—C7—N1	118.52 (15)	C21—C20—N2	119.78 (16)
C12—C7—N1	122.01 (16)	C25—C20—N2	120.94 (16)
C7—C8—C9	119.90 (17)	C22—C21—C20	120.32 (18)
C7—C8—H8	120.0	C22—C21—H21	119.8
C9—C8—H8	120.0	C20—C21—H21	119.8
C10—C9—C8	121.69 (19)	C21—C22—C23	121.54 (19)
C10—C9—H9	119.2	C21—C22—H22	119.2
C8—C9—H9	119.2	C23—C22—H22	119.2
C9—C10—C11	117.77 (17)	C22—C23—C24	117.65 (18)
C9—C10—C13	121.4 (2)	C22—C23—C26	121.4 (2)
C11—C10—C13	120.8 (2)	C24—C23—C26	120.9 (2)
C10—C11—C12	121.79 (18)	C23—C24—C25	121.82 (19)
C10—C11—H11	119.1	C23—C24—H24	119.1
C12—C11—H11	119.1	C25—C24—H24	119.1
C11—C12—C7	119.47 (18)	C20—C25—C24	119.41 (18)
C11—C12—H12	120.3	C20—C25—H25	120.3
C7—C12—H12	120.3	C24—C25—H25	120.3
C10—C13—H13A	109.5	C23—C26—H26A	109.5
C10—C13—H13B	109.5	C23—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C10—C13—H13C	109.5	C23—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C7—N1—S1	124.67 (12)	C20—N2—S2	121.62 (11)
C7—N1—H1N	111.7 (15)	C20—N2—H2N	119.2 (13)
S1—N1—H1N	110.6 (14)	S2—N2—H2N	107.9 (13)
O2—S1—O1	118.67 (8)	O4—S2—O3	119.13 (9)
O2—S1—N1	107.94 (8)	O4—S2—N2	108.54 (9)
O1—S1—N1	105.17 (8)	O3—S2—N2	105.02 (8)
O2—S1—C1	107.24 (8)	O4—S2—C14	107.85 (9)
O1—S1—C1	108.18 (8)	O3—S2—C14	108.93 (9)
N1—S1—C1	109.42 (8)	N2—S2—C14	106.74 (8)
C6—C1—C2—C3	1.1 (3)	C19—C14—C15—C16	0.3 (3)
S1—C1—C2—C3	−177.38 (17)	S2—C14—C15—C16	−177.47 (16)
C1—C2—C3—C4	−0.6 (4)	C14—C15—C16—C17	0.1 (3)
C2—C3—C4—C5	−0.4 (4)	C15—C16—C17—C18	−0.1 (4)
C3—C4—C5—C6	0.9 (4)	C16—C17—C18—C19	−0.3 (5)
C2—C1—C6—C5	−0.6 (3)	C15—C14—C19—C18	−0.6 (3)
S1—C1—C6—C5	177.87 (14)	S2—C14—C19—C18	177.13 (18)
C4—C5—C6—C1	−0.4 (3)	C17—C18—C19—C14	0.6 (4)
C12—C7—C8—C9	−0.2 (3)	C25—C20—C21—C22	0.5 (3)
N1—C7—C8—C9	−176.66 (16)	N2—C20—C21—C22	178.13 (16)
C7—C8—C9—C10	−0.5 (3)	C20—C21—C22—C23	0.9 (3)
C8—C9—C10—C11	0.6 (3)	C21—C22—C23—C24	−1.3 (3)
C8—C9—C10—C13	179.84 (19)	C21—C22—C23—C26	179.8 (2)
C9—C10—C11—C12	−0.1 (3)	C22—C23—C24—C25	0.3 (3)
C13—C10—C11—C12	−179.32 (19)	C26—C23—C24—C25	179.2 (2)
C10—C11—C12—C7	−0.5 (3)	C21—C20—C25—C24	−1.5 (3)
C8—C7—C12—C11	0.7 (3)	N2—C20—C25—C24	−179.07 (17)
N1—C7—C12—C11	177.04 (16)	C23—C24—C25—C20	1.1 (3)
C8—C7—N1—S1	−133.52 (16)	C21—C20—N2—S2	118.91 (17)
C12—C7—N1—S1	50.1 (2)	C25—C20—N2—S2	−63.5 (2)
C7—N1—S1—O2	−56.90 (16)	C20—N2—S2—O4	60.77 (16)
C7—N1—S1—O1	175.49 (14)	C20—N2—S2—O3	−170.79 (14)
C7—N1—S1—C1	59.49 (17)	C20—N2—S2—C14	−55.23 (16)
C6—C1—S1—O2	−172.89 (14)	C15—C14—S2—O4	−166.93 (15)
C2—C1—S1—O2	5.65 (17)	C19—C14—S2—O4	15.29 (19)
C6—C1—S1—O1	−43.79 (16)	C15—C14—S2—O3	62.44 (18)
C2—C1—S1—O1	134.75 (15)	C19—C14—S2—O3	−115.33 (17)
C6—C1—S1—N1	70.28 (16)	C15—C14—S2—N2	−50.46 (17)
C2—C1—S1—N1	−111.19 (16)	C19—C14—S2—N2	131.76 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (1)	2.09 (1)	2.924 (2)	166 (2)
N2—H2N···O1	0.85 (1)	2.17 (1)	3.0056 (19)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (1)	2.09 (1)	2.924 (2)	166 (2)
N2—H2N⋯O1	0.85 (1)	2.17 (1)	3.0056 (19)	168 (2)

Symmetry code: (i) .