N-(3-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 two aromatic rings are 67.9 (1) and 68.6 (1)° in the two mol-ecules. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains.

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 ▶); Nirmala et al. (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H13NO2S

M = 247.30

Orthorhombic,

a = 8.787 (1) Å

b = 8.884 (1) Å

c = 32.406 (3) Å

V = 2529.7 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.19 mm−1

T = 299 K

0.60 × 0.60 × 0.35 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.353, T max = 0.514

3284 measured reflections

3109 independent reflections

3002 reflections with I > 2σ(I)

R int = 0.039

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.01

3109 reflections

316 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 507 Friedel pairs

Flack parameter: −0.010 (17)

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/S1600536810002291/bt5172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002291/bt5172Isup2.hkl

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

C13H13NO2S	F(000) = 1040
Mr = 247.30	Dx = 1.299 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 8.787 (1) Å	θ = 6.5–20.2°
b = 8.884 (1) Å	µ = 2.19 mm−1
c = 32.406 (3) Å	T = 299 K
V = 2529.7 (5) Å3	Prism, colourless
Z = 8	0.60 × 0.60 × 0.35 mm

Enraf–Nonius CAD-4 diffractometer	3002 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 66.9°, θmin = 2.7°
ω/2θ scans	h = −10→0
Absorption correction: ψ scan (North et al., 1968)	k = −10→1
Tmin = 0.353, Tmax = 0.514	l = −38→4
3284 measured reflections	3 standard reflections every 120 min
3109 independent reflections	intensity decay: 1.0%

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)] = 0.033	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.4153P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.18 e Å−3
3109 reflections	Δρmin = −0.36 e Å−3
316 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0203 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 507 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.010 (17)

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	0.24673 (6)	0.87533 (7)	0.002545 (17)	0.05084 (19)
O1	0.08754 (19)	0.8919 (2)	0.01175 (6)	0.0660 (5)
O2	0.2926 (2)	0.8620 (3)	−0.03936 (5)	0.0675 (5)
N1	0.3085 (2)	0.7245 (3)	0.02524 (6)	0.0534 (5)
H1N	0.394 (4)	0.710 (4)	0.0126 (9)	0.064*
C1	0.3398 (3)	1.0308 (3)	0.02455 (8)	0.0548 (6)
C2	0.4797 (4)	1.0708 (4)	0.00878 (10)	0.0740 (8)
H2	0.5241	1.0147	−0.0123	0.089*
C3	0.5529 (6)	1.1951 (5)	0.02461 (13)	0.1007 (13)
H3	0.6475	1.2232	0.0144	0.121*
C4	0.4868 (7)	1.2767 (5)	0.05524 (16)	0.1167 (17)
H4	0.5363	1.3615	0.0653	0.140*
C5	0.3486 (6)	1.2364 (5)	0.07158 (15)	0.1124 (15)
H5	0.3054	1.2924	0.0928	0.135*
C6	0.2731 (4)	1.1093 (4)	0.05579 (10)	0.0816 (9)
H6	0.1795	1.0794	0.0665	0.098*
C7	0.3008 (3)	0.7054 (3)	0.06911 (7)	0.0502 (5)
C8	0.4334 (3)	0.6721 (3)	0.09016 (8)	0.0563 (6)
H8	0.5254	0.6688	0.0760	0.068*
C9	0.4301 (4)	0.6434 (4)	0.13244 (8)	0.0675 (7)
C10	0.2930 (4)	0.6565 (4)	0.15269 (9)	0.0758 (9)
H10	0.2891	0.6403	0.1810	0.091*
C11	0.1614 (4)	0.6932 (4)	0.13180 (10)	0.0793 (9)
H11	0.0706	0.7034	0.1462	0.095*
C12	0.1636 (3)	0.7147 (4)	0.08980 (9)	0.0671 (7)
H12	0.0741	0.7352	0.0755	0.081*
C13	0.5728 (5)	0.6023 (6)	0.15481 (11)	0.0973 (12)
H13A	0.5927	0.4968	0.1513	0.117*
H13B	0.5612	0.6242	0.1836	0.117*
H13C	0.6564	0.6594	0.1439	0.117*
S2	0.11402 (7)	0.27358 (7)	0.246445 (17)	0.05112 (19)
O3	0.1367 (2)	0.4283 (2)	0.23607 (6)	0.0637 (5)
O4	0.0977 (2)	0.2326 (2)	0.28860 (5)	0.0676 (5)
N2	−0.0417 (2)	0.2159 (3)	0.22416 (6)	0.0527 (5)
H2N	−0.065 (4)	0.136 (4)	0.2348 (8)	0.063*
C14	0.2668 (3)	0.1716 (3)	0.22523 (7)	0.0532 (6)
C15	0.2926 (3)	0.0270 (4)	0.23940 (9)	0.0674 (7)
H15	0.2299	−0.0157	0.2593	0.081*
C16	0.4143 (5)	−0.0526 (4)	0.22311 (12)	0.0902 (10)
H16	0.4344	−0.1497	0.2323	0.108*
C17	0.5046 (4)	0.0106 (5)	0.19371 (14)	0.0998 (13)
H17	0.5863	−0.0438	0.1832	0.120*
C18	0.4775 (5)	0.1509 (6)	0.17945 (14)	0.1068 (14)
H18	0.5396	0.1913	0.1590	0.128*
C19	0.3571 (4)	0.2356 (4)	0.19508 (10)	0.0821 (9)
H19	0.3381	0.3324	0.1855	0.099*
C20	−0.0626 (3)	0.2246 (3)	0.18014 (7)	0.0504 (5)
C21	−0.1049 (3)	0.0949 (3)	0.15949 (8)	0.0539 (6)
H21	−0.1118	0.0046	0.1739	0.065*
C22	−0.1374 (3)	0.0981 (4)	0.11760 (8)	0.0609 (6)
C23	−0.1195 (4)	0.2328 (4)	0.09707 (9)	0.0729 (8)
H23	−0.1369	0.2369	0.0688	0.087*
C24	−0.0769 (5)	0.3601 (4)	0.11743 (10)	0.0847 (10)
H24	−0.0661	0.4496	0.1028	0.102*
C25	−0.0492 (4)	0.3584 (4)	0.15961 (9)	0.0705 (8)
H25	−0.0223	0.4460	0.1735	0.085*
C26	−0.1914 (5)	−0.0405 (4)	0.09576 (11)	0.0861 (10)
H26A	−0.1587	−0.1280	0.1107	0.103*
H26B	−0.1496	−0.0429	0.0684	0.103*
H26C	−0.3005	−0.0394	0.0942	0.103*

	U11	U22	U33	U12	U13	U23
S1	0.0439 (3)	0.0637 (3)	0.0449 (3)	−0.0013 (3)	−0.0050 (2)	−0.0031 (3)
O1	0.0395 (8)	0.0884 (13)	0.0702 (11)	0.0026 (9)	−0.0048 (8)	−0.0042 (11)
O2	0.0692 (12)	0.0883 (13)	0.0450 (8)	−0.0003 (11)	−0.0035 (8)	−0.0041 (10)
N1	0.0497 (10)	0.0613 (12)	0.0492 (10)	0.0043 (10)	0.0060 (9)	−0.0033 (10)
C1	0.0554 (14)	0.0568 (13)	0.0523 (13)	−0.0011 (12)	−0.0138 (11)	0.0063 (12)
C2	0.0700 (17)	0.0829 (19)	0.0690 (18)	−0.0202 (17)	−0.0053 (14)	0.0104 (16)
C3	0.107 (3)	0.095 (3)	0.101 (3)	−0.044 (2)	−0.021 (2)	0.017 (2)
C4	0.139 (4)	0.073 (2)	0.138 (4)	−0.029 (3)	−0.054 (3)	0.003 (3)
C5	0.130 (4)	0.090 (3)	0.117 (3)	0.014 (3)	−0.031 (3)	−0.038 (3)
C6	0.083 (2)	0.082 (2)	0.0793 (18)	0.0032 (19)	−0.0102 (17)	−0.0229 (18)
C7	0.0525 (12)	0.0477 (12)	0.0503 (11)	−0.0035 (11)	0.0060 (10)	−0.0011 (11)
C8	0.0538 (14)	0.0587 (14)	0.0564 (13)	−0.0038 (12)	0.0040 (11)	0.0002 (12)
C9	0.0789 (18)	0.0656 (17)	0.0580 (14)	−0.0086 (16)	−0.0088 (14)	0.0048 (14)
C10	0.097 (2)	0.0811 (19)	0.0496 (13)	−0.0142 (19)	0.0120 (15)	0.0081 (15)
C11	0.078 (2)	0.091 (2)	0.0682 (17)	−0.0070 (19)	0.0266 (16)	0.0095 (17)
C12	0.0560 (14)	0.0802 (18)	0.0651 (15)	−0.0021 (15)	0.0115 (13)	0.0086 (15)
C13	0.093 (3)	0.120 (3)	0.079 (2)	0.001 (3)	−0.0190 (19)	0.022 (2)
S2	0.0540 (3)	0.0561 (3)	0.0432 (3)	0.0010 (3)	0.0032 (2)	−0.0055 (2)
O3	0.0722 (12)	0.0541 (9)	0.0649 (11)	−0.0015 (9)	0.0044 (9)	−0.0077 (8)
O4	0.0777 (12)	0.0808 (12)	0.0444 (8)	0.0005 (12)	0.0036 (8)	−0.0037 (9)
N2	0.0503 (10)	0.0584 (11)	0.0493 (10)	−0.0057 (10)	0.0036 (9)	0.0040 (10)
C14	0.0456 (12)	0.0639 (14)	0.0500 (12)	0.0015 (11)	−0.0032 (11)	−0.0098 (11)
C15	0.0641 (17)	0.0689 (16)	0.0693 (16)	0.0066 (14)	0.0029 (13)	−0.0031 (15)
C16	0.086 (2)	0.077 (2)	0.107 (3)	0.025 (2)	−0.005 (2)	−0.007 (2)
C17	0.068 (2)	0.106 (3)	0.125 (3)	0.024 (2)	0.017 (2)	−0.020 (3)
C18	0.082 (2)	0.119 (3)	0.119 (3)	0.020 (3)	0.045 (2)	0.011 (3)
C19	0.0743 (19)	0.085 (2)	0.087 (2)	0.0097 (19)	0.0281 (17)	0.0082 (19)
C20	0.0423 (11)	0.0606 (14)	0.0483 (11)	0.0029 (11)	0.0021 (9)	0.0032 (12)
C21	0.0503 (12)	0.0555 (13)	0.0561 (12)	0.0054 (12)	0.0044 (11)	0.0010 (11)
C22	0.0504 (13)	0.0743 (16)	0.0579 (13)	0.0047 (13)	0.0017 (11)	−0.0086 (13)
C23	0.0739 (18)	0.093 (2)	0.0519 (13)	−0.009 (2)	−0.0078 (13)	0.0054 (15)
C24	0.100 (3)	0.087 (2)	0.0675 (17)	−0.018 (2)	−0.0173 (18)	0.0265 (17)
C25	0.085 (2)	0.0646 (16)	0.0625 (15)	−0.0112 (16)	−0.0115 (15)	0.0075 (14)
C26	0.097 (2)	0.082 (2)	0.0790 (19)	0.002 (2)	−0.0076 (19)	−0.0239 (18)

S1—O2	1.4214 (18)	S2—O4	1.4212 (18)
S1—O1	1.4378 (18)	S2—O3	1.429 (2)
S1—N1	1.622 (2)	S2—N2	1.630 (2)
S1—C1	1.756 (3)	S2—C14	1.760 (3)
N1—C7	1.433 (3)	N2—C20	1.440 (3)
N1—H1N	0.87 (3)	N2—H2N	0.82 (3)
C1—C6	1.362 (4)	C14—C19	1.381 (4)
C1—C2	1.379 (4)	C14—C15	1.383 (4)
C2—C3	1.377 (5)	C15—C16	1.386 (5)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.359 (6)	C16—C17	1.361 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.373 (7)	C17—C18	1.350 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.406 (6)	C18—C19	1.393 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.382 (4)	C20—C25	1.367 (4)
C7—C8	1.382 (4)	C20—C21	1.383 (4)
C8—C9	1.394 (3)	C21—C22	1.387 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.377 (5)	C22—C23	1.378 (4)
C9—C13	1.494 (5)	C22—C26	1.497 (4)
C10—C11	1.379 (5)	C23—C24	1.362 (5)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.375 (4)	C24—C25	1.388 (4)
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
O2—S1—O1	118.86 (11)	O4—S2—O3	119.12 (12)
O2—S1—N1	105.62 (12)	O4—S2—N2	105.12 (12)
O1—S1—N1	108.43 (12)	O3—S2—N2	108.38 (12)
O2—S1—C1	108.75 (13)	O4—S2—C14	108.70 (12)
O1—S1—C1	106.75 (13)	O3—S2—C14	107.27 (12)
N1—S1—C1	108.04 (11)	N2—S2—C14	107.80 (12)
C7—N1—S1	122.14 (18)	C20—N2—S2	121.91 (17)
C7—N1—H1N	119.3 (19)	C20—N2—H2N	116 (2)
S1—N1—H1N	102 (2)	S2—N2—H2N	107 (2)
C6—C1—C2	121.8 (3)	C19—C14—C15	121.6 (3)
C6—C1—S1	120.3 (2)	C19—C14—S2	120.2 (2)
C2—C1—S1	117.9 (2)	C15—C14—S2	118.3 (2)
C3—C2—C1	119.0 (4)	C14—C15—C16	118.3 (3)
C3—C2—H2	120.5	C14—C15—H15	120.9
C1—C2—H2	120.5	C16—C15—H15	120.9
C4—C3—C2	120.0 (4)	C17—C16—C15	120.4 (4)
C4—C3—H3	120.0	C17—C16—H16	119.8
C2—C3—H3	120.0	C15—C16—H16	119.8
C3—C4—C5	121.4 (4)	C18—C17—C16	121.1 (4)
C3—C4—H4	119.3	C18—C17—H17	119.4
C5—C4—H4	119.3	C16—C17—H17	119.4
C4—C5—C6	119.1 (4)	C17—C18—C19	120.5 (4)
C4—C5—H5	120.4	C17—C18—H18	119.7
C6—C5—H5	120.4	C19—C18—H18	119.7
C1—C6—C5	118.6 (4)	C14—C19—C18	118.1 (4)
C1—C6—H6	120.7	C14—C19—H19	121.0
C5—C6—H6	120.7	C18—C19—H19	121.0
C12—C7—C8	120.6 (2)	C25—C20—C21	120.8 (2)
C12—C7—N1	121.0 (2)	C25—C20—N2	121.2 (3)
C8—C7—N1	118.4 (2)	C21—C20—N2	117.9 (2)
C7—C8—C9	120.5 (3)	C20—C21—C22	120.8 (2)
C7—C8—H8	119.8	C20—C21—H21	119.6
C9—C8—H8	119.8	C22—C21—H21	119.6
C10—C9—C8	118.1 (3)	C23—C22—C21	117.8 (3)
C10—C9—C13	121.6 (3)	C23—C22—C26	121.5 (3)
C8—C9—C13	120.3 (3)	C21—C22—C26	120.7 (3)
C9—C10—C11	121.3 (2)	C24—C23—C22	121.2 (3)
C9—C10—H10	119.4	C24—C23—H23	119.4
C11—C10—H10	119.4	C22—C23—H23	119.4
C12—C11—C10	120.5 (3)	C23—C24—C25	121.1 (3)
C12—C11—H11	119.7	C23—C24—H24	119.5
C10—C11—H11	119.7	C25—C24—H24	119.5
C11—C12—C7	118.9 (3)	C20—C25—C24	118.3 (3)
C11—C12—H12	120.5	C20—C25—H25	120.9
C7—C12—H12	120.5	C24—C25—H25	120.9
C9—C13—H13A	109.5	C22—C26—H26A	109.5
C9—C13—H13B	109.5	C22—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C9—C13—H13C	109.5	C22—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
O2—S1—N1—C7	172.1 (2)	O4—S2—N2—C20	−174.2 (2)
O1—S1—N1—C7	−59.5 (2)	O3—S2—N2—C20	57.4 (2)
C1—S1—N1—C7	55.8 (2)	C14—S2—N2—C20	−58.4 (3)
O2—S1—C1—C6	150.7 (2)	O4—S2—C14—C19	−146.4 (3)
O1—S1—C1—C6	21.3 (3)	O3—S2—C14—C19	−16.4 (3)
N1—S1—C1—C6	−95.2 (3)	N2—S2—C14—C19	100.1 (3)
O2—S1—C1—C2	−28.4 (3)	O4—S2—C14—C15	33.9 (2)
O1—S1—C1—C2	−157.8 (2)	O3—S2—C14—C15	163.9 (2)
N1—S1—C1—C2	85.8 (2)	N2—S2—C14—C15	−79.6 (2)
C6—C1—C2—C3	−1.1 (5)	C19—C14—C15—C16	1.2 (4)
S1—C1—C2—C3	178.0 (3)	S2—C14—C15—C16	−179.1 (3)
C1—C2—C3—C4	−0.3 (5)	C14—C15—C16—C17	−0.5 (5)
C2—C3—C4—C5	1.3 (7)	C15—C16—C17—C18	−0.6 (7)
C3—C4—C5—C6	−1.0 (7)	C16—C17—C18—C19	1.0 (8)
C2—C1—C6—C5	1.4 (5)	C15—C14—C19—C18	−0.8 (5)
S1—C1—C6—C5	−177.7 (3)	S2—C14—C19—C18	179.5 (3)
C4—C5—C6—C1	−0.3 (6)	C17—C18—C19—C14	−0.3 (7)
S1—N1—C7—C12	57.0 (3)	S2—N2—C20—C25	−56.3 (3)
S1—N1—C7—C8	−125.3 (2)	S2—N2—C20—C21	127.3 (2)
C12—C7—C8—C9	1.7 (4)	C25—C20—C21—C22	−1.1 (4)
N1—C7—C8—C9	−176.1 (3)	N2—C20—C21—C22	175.4 (2)
C7—C8—C9—C10	−3.1 (5)	C20—C21—C22—C23	2.8 (4)
C7—C8—C9—C13	177.9 (3)	C20—C21—C22—C26	−176.7 (3)
C8—C9—C10—C11	1.6 (5)	C21—C22—C23—C24	−2.4 (5)
C13—C9—C10—C11	−179.4 (4)	C26—C22—C23—C24	177.1 (3)
C9—C10—C11—C12	1.3 (6)	C22—C23—C24—C25	0.3 (6)
C10—C11—C12—C7	−2.8 (5)	C21—C20—C25—C24	−1.0 (5)
C8—C7—C12—C11	1.2 (5)	N2—C20—C25—C24	−177.4 (3)
N1—C7—C12—C11	178.9 (3)	C23—C24—C25—C20	1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (3)	2.08 (3)	2.919 (3)	162 (3)
N2—H2N···O3ii	0.82 (3)	2.17 (3)	2.981 (3)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (3)	2.08 (3)	2.919 (3)	162 (3)
N2—H2N⋯O3ii	0.82 (3)	2.17 (3)	2.981 (3)	178 (3)

Symmetry codes: (i) ; (ii) .