1-(o-Tol-yl)thio-urea.

In the title compound, C(8)H(10)N(2)S, the o-tolyl group and the thio-urea core are planar. The mean planes of the two groups are almost perpendicular [82.19 (8)°]. The thio-urea group is in the thio-amide form, in which resonance is present. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯S hydrogen bonds, forming two infinite chains parallel to the (110) and (10) planes.

Related literature

For general background, see: Koketsu & Ishihara (2006 ▶); Struga et al. (2007 ▶). For related structures, see: Corrêa et al. (2006 ▶); Corrêa et al. (2008 ▶); Estévez-Hernández et al. (2008 ▶); Duque et al. (2008 ▶). For the synthesis, see: Otazo-Sánches et al. (2001 ▶). For related literature, see: Otazo et al. (2001 ▶); Ramadas et al. (1998 ▶).

Experimental

Crystal data

C8H10N2S

M = 166.25

Monoclinic,

a = 15.1323 (3) Å

b = 7.7965 (2) Å

c = 15.3222 (4) Å

β = 90.828 (2)°

V = 1807.61 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 294 K

0.31 × 0.22 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (Coppens et al., 1965 ▶) T min = 0.973, T max = 0.991

6748 measured reflections

1914 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.140

S = 1.03

1914 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DEn class="Chemical">NZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024161/fb2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024161/fb2105Isup2.hkl

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

C8H10N2S	F000 = 704
Mr = 166.25	Dx = 1.222 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 15611 reflections
a = 15.1323 (3) Å	θ = 2.9–26.7º
b = 7.7965 (2) Å	µ = 0.30 mm−1
c = 15.3222 (4) Å	T = 294 K
β = 90.828 (2)º	Prism, colourless
V = 1807.61 (8) Å3	0.31 × 0.22 × 0.10 mm
Z = 8

Nonius KappaCCD diffractometer	1438 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Enraf Nonius FR590	Rint = 0.031
Monochromator: horizontally mounted graphite crystal	θmax = 26.8º
φ scans and ω scans winth κ offsets	θmin = 3.8º
Absorption correction: gaussian(Coppens et al., 1965)	h = −19→18
Tmin = 0.973, Tmax = 0.991	k = −9→9
6748 measured reflections	l = −19→19
1914 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0896P)2 + 0.2205P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1914 reflections	Δρmax = 0.19 e Å−3
101 parameters	Δρmin = −0.21 e Å−3
40 constraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.11314 (11)	0.8287 (2)	0.06714 (12)	0.0577 (5)
C2	0.15409 (11)	0.6359 (3)	0.18736 (12)	0.0611 (5)
C3	0.12742 (14)	0.4692 (3)	0.18788 (14)	0.0740 (6)
C4	0.11722 (18)	0.3923 (3)	0.27051 (17)	0.0886 (7)
H4	0.0995	0.2783	0.2737	0.106*
C5	0.13277 (17)	0.4810 (4)	0.34545 (15)	0.0887 (7)
H5	0.1256	0.4269	0.399	0.106*
C6	0.15879 (16)	0.6486 (4)	0.34321 (15)	0.0884 (7)
H6	0.1691	0.7089	0.3947	0.106*
C7	0.16938 (15)	0.7262 (3)	0.26419 (14)	0.0769 (6)
H7	0.187	0.8404	0.2618	0.092*
C8	0.1108 (2)	0.3713 (4)	0.10584 (18)	0.1082 (9)
H8A	0.0882	0.2598	0.1197	0.162*
H8B	0.1651	0.3594	0.0748	0.162*
H8C	0.0685	0.4317	0.0701	0.162*
N1	0.16917 (10)	0.7203 (2)	0.10564 (10)	0.0665 (5)
H1	0.218	0.6992	0.0797	0.08*
N2	0.03568 (11)	0.8514 (3)	0.10408 (12)	0.0897 (7)
H2A	0.0232	0.797	0.1512	0.108*
H2B	−0.0023	0.9205	0.081	0.108*
S1	0.14045 (3)	0.93276 (6)	−0.02514 (3)	0.0663 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0496 (9)	0.0631 (10)	0.0607 (10)	0.0091 (8)	0.0069 (8)	0.0058 (8)
C2	0.0486 (9)	0.0738 (12)	0.0610 (11)	0.0136 (8)	0.0074 (8)	0.0143 (9)
C3	0.0718 (13)	0.0793 (14)	0.0711 (13)	0.0099 (11)	0.0082 (10)	0.0043 (10)
C4	0.0938 (16)	0.0817 (14)	0.0906 (17)	0.0062 (12)	0.0181 (14)	0.0225 (13)
C5	0.0963 (16)	0.1078 (18)	0.0624 (13)	0.0242 (15)	0.0148 (11)	0.0210 (13)
C6	0.0920 (16)	0.1113 (19)	0.0619 (13)	0.0199 (14)	0.0023 (11)	0.0010 (13)
C7	0.0741 (13)	0.0871 (14)	0.0696 (13)	0.0052 (11)	0.0053 (10)	0.0012 (11)
C8	0.130 (2)	0.1022 (18)	0.0930 (18)	−0.0140 (18)	0.0182 (17)	−0.0160 (16)
N1	0.0539 (8)	0.0834 (11)	0.0626 (9)	0.0202 (7)	0.0146 (7)	0.0205 (8)
N2	0.0616 (10)	0.1243 (16)	0.0838 (12)	0.0374 (10)	0.0250 (9)	0.0451 (12)
S1	0.0622 (4)	0.0697 (4)	0.0673 (4)	0.0189 (2)	0.0158 (2)	0.0183 (2)

C1—N2	1.321 (2)	C5—H5	0.93
C1—N1	1.329 (2)	C6—C7	1.365 (3)
C1—S1	1.6868 (18)	C6—H6	0.93
C2—C3	1.361 (3)	C7—H7	0.93
C2—C7	1.388 (3)	C8—H8A	0.96
C2—N1	1.435 (2)	C8—H8B	0.96
C3—C4	1.411 (3)	C8—H8C	0.96
C3—C8	1.489 (3)	N1—H1	0.86
C4—C5	1.358 (4)	N2—H2A	0.86
C4—H4	0.93	N2—H2B	0.86
C5—C6	1.365 (4)
N2—C1—N1	117.34 (16)	C5—C6—H6	120.5
N2—C1—S1	121.63 (14)	C6—C7—C2	120.5 (2)
N1—C1—S1	121.03 (13)	C6—C7—H7	119.8
C3—C2—C7	121.68 (19)	C2—C7—H7	119.8
C3—C2—N1	119.57 (19)	C3—C8—H8A	109.5
C7—C2—N1	118.73 (19)	C3—C8—H8B	109.5
C2—C3—C4	116.6 (2)	H8A—C8—H8B	109.5
C2—C3—C8	122.1 (2)	C3—C8—H8C	109.5
C4—C3—C8	121.4 (2)	H8A—C8—H8C	109.5
C5—C4—C3	121.5 (2)	H8B—C8—H8C	109.5
C5—C4—H4	119.3	C1—N1—C2	124.75 (15)
C3—C4—H4	119.3	C1—N1—H1	117.6
C4—C5—C6	120.9 (2)	C2—N1—H1	117.6
C4—C5—H5	119.6	C1—N2—H2A	120
C6—C5—H5	119.6	C1—N2—H2B	120
C7—C6—C5	119.0 (2)	H2A—N2—H2B	120
C7—C6—H6	120.5
C7—C2—C3—C4	−0.8 (3)	C5—C6—C7—C2	−0.1 (3)
N1—C2—C3—C4	177.56 (18)	C3—C2—C7—C6	0.7 (3)
C7—C2—C3—C8	180.0 (2)	N1—C2—C7—C6	−177.68 (18)
N1—C2—C3—C8	−1.7 (3)	N2—C1—N1—C2	−4.6 (3)
C2—C3—C4—C5	0.4 (3)	S1—C1—N1—C2	175.28 (16)
C8—C3—C4—C5	179.6 (3)	C3—C2—N1—C1	101.4 (2)
C3—C4—C5—C6	0.1 (4)	C7—C2—N1—C1	−80.2 (3)
C4—C5—C6—C7	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.86	2.53	3.368 (2)	165
N2—H2B···S1ii	0.86	2.52	3.362 (2)	166

C1—N2	1.321 (2)
C1—N1	1.329 (2)
C1—S1	1.6868 (18)
C2—N1	1.435 (2)

N2—C1—N1	117.34 (16)
N2—C1—S1	121.63 (14)
N1—C1—S1	121.03 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.86	2.53	3.368 (2)	165
N2—H2B⋯S1ii	0.86	2.52	3.362 (2)	166

Symmetry codes: (i) ; (ii) .