1-Methyl-3-phenyl-thio-urea.

The title compound, C8H10N2S, was prepared by reaction of methyl-amine solution, KOH and phenyl-iso-thio-cyanate in ethanol. It adopts a syn-Me and anti-Ph conformation relative to the C=S double bond. The dihedral angle between the N-C(=S)-N thio-urea and phenyl planes is 67.83 (6)°. In the crystal, the mol-ecules centrosymmetrical dimers by pairs of N(Ph)-H⋯S hydrogen bonds. The dimers are linked by N(Me)-H⋯S hydrogen bonds into layers parallel to (100).

Related literature

For applications of thio­urea derivatives, see: Madan & Taneja (1991 ▶); Xu et al. (2004 ▶); Borisova et al. (2007 ▶). For the crystal structures of related compounds, see: Ji et al. (2002 ▶); Wenzel et al. (2011 ▶).

Experimental

Crystal data

C8H10N2S

M = 166.24

Monoclinic,

a = 17.348 (3) Å

b = 8.6023 (13) Å

c = 12.1672 (18) Å

β = 99.637 (3)°

V = 1790.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

5444 measured reflections

2026 independent reflections

1424 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.03

2026 reflections

109 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker 1997 ▶); cell refinement: SAINT (Bruker 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007442/kq2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007442/kq2012Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007442/kq2012Isup3.cml

CCDC reference: 995308

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H10N2S	F(000) = 704
Mr = 166.24	Dx = 1.234 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.348 (3) Å	Cell parameters from 1286 reflections
b = 8.6023 (13) Å	θ = 2.4–24.8°
c = 12.1672 (18) Å	µ = 0.30 mm−1
β = 99.637 (3)°	T = 296 K
V = 1790.1 (5) Å3	Bar, colorless
Z = 8	0.25 × 0.23 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.033
Radiation source: sealed tube	θmax = 27.5°, θmin = 2.4°
phi and ω scans	h = −22→21
5444 measured reflections	k = −8→11
2026 independent reflections	l = −15→15
1424 reflections with I > 2σ(I)

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1272P] where P = (Fo2 + 2Fc2)/3
2026 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
S1	0.16423 (3)	1.19173 (6)	0.35515 (4)	0.04468 (19)
N1	0.29456 (9)	1.0463 (2)	0.43958 (15)	0.0467 (5)
N2	0.23002 (10)	0.9493 (2)	0.27416 (15)	0.0485 (5)
C1	0.35645 (10)	0.9351 (2)	0.45446 (17)	0.0401 (5)
C2	0.36233 (13)	0.8311 (3)	0.5403 (2)	0.0648 (7)
H2A	0.3251	0.8303	0.5871	0.078*
C3	0.42442 (15)	0.7264 (3)	0.5572 (3)	0.0814 (9)
H3	0.4287	0.6555	0.6156	0.098*
C4	0.47899 (13)	0.7275 (3)	0.4884 (3)	0.0683 (7)
H4	0.5202	0.6569	0.4997	0.082*
C5	0.47334 (12)	0.8309 (3)	0.4037 (2)	0.0646 (7)
H5	0.5109	0.8317	0.3573	0.077*
C6	0.41193 (11)	0.9357 (3)	0.38576 (18)	0.0510 (5)
H6	0.4082	1.0064	0.3273	0.061*
C7	0.23382 (9)	1.0531 (2)	0.35543 (15)	0.0353 (4)
C8	0.16755 (12)	0.9440 (3)	0.1781 (2)	0.0685 (7)
H8A	0.1740	1.0278	0.1284	0.103*
H8B	0.1180	0.9540	0.2026	0.103*
H8C	0.1695	0.8467	0.1401	0.103*
H1	0.2993 (12)	1.117 (3)	0.4843 (19)	0.054 (7)*
H2	0.2646 (12)	0.893 (3)	0.2769 (18)	0.052 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0346 (3)	0.0467 (3)	0.0524 (3)	0.0114 (2)	0.0062 (2)	0.0000 (2)
N1	0.0401 (9)	0.0497 (11)	0.0462 (11)	0.0157 (8)	−0.0043 (8)	−0.0147 (9)
N2	0.0365 (9)	0.0573 (12)	0.0482 (11)	0.0134 (8)	−0.0034 (8)	−0.0132 (9)
C1	0.0293 (8)	0.0418 (11)	0.0457 (11)	0.0061 (8)	−0.0044 (8)	−0.0085 (9)
C2	0.0512 (13)	0.0680 (17)	0.0758 (17)	0.0096 (11)	0.0123 (12)	0.0206 (13)
C3	0.0690 (17)	0.0612 (18)	0.109 (2)	0.0133 (14)	0.0015 (16)	0.0307 (16)
C4	0.0427 (12)	0.0587 (16)	0.097 (2)	0.0177 (11)	−0.0081 (13)	−0.0096 (15)
C5	0.0364 (10)	0.090 (2)	0.0637 (16)	0.0163 (11)	−0.0007 (10)	−0.0205 (14)
C6	0.0397 (10)	0.0647 (15)	0.0465 (12)	0.0101 (10)	0.0009 (9)	−0.0033 (11)
C7	0.0298 (9)	0.0394 (11)	0.0373 (10)	0.0024 (7)	0.0075 (8)	0.0004 (9)
C8	0.0504 (12)	0.093 (2)	0.0555 (14)	0.0138 (12)	−0.0108 (11)	−0.0244 (14)

S1—C7	1.6964 (17)	C3—C4	1.365 (4)
N1—C7	1.342 (2)	C3—H3	0.9300
N1—C1	1.427 (2)	C4—C5	1.353 (4)
N1—H1	0.81 (2)	C4—H4	0.9300
N2—C7	1.326 (2)	C5—C6	1.384 (3)
N2—C8	1.455 (3)	C5—H5	0.9300
N2—H2	0.77 (2)	C6—H6	0.9300
C1—C2	1.366 (3)	C8—H8A	0.9600
C1—C6	1.376 (3)	C8—H8B	0.9600
C2—C3	1.393 (3)	C8—H8C	0.9600
C2—H2A	0.9300
C7—N1—C1	127.17 (17)	C3—C4—H4	119.9
C7—N1—H1	117.4 (16)	C4—C5—C6	120.2 (2)
C1—N1—H1	115.2 (16)	C4—C5—H5	119.9
C7—N2—C8	123.87 (18)	C6—C5—H5	119.9
C7—N2—H2	117.0 (17)	C1—C6—C5	120.0 (2)
C8—N2—H2	119.0 (17)	C1—C6—H6	120.0
C2—C1—C6	119.74 (18)	C5—C6—H6	120.0
C2—C1—N1	119.64 (18)	N2—C7—N1	118.32 (17)
C6—C1—N1	120.57 (18)	N2—C7—S1	121.70 (15)
C1—C2—C3	119.6 (2)	N1—C7—S1	119.98 (14)
C1—C2—H2A	120.2	N2—C8—H8A	109.5
C3—C2—H2A	120.2	N2—C8—H8B	109.5
C4—C3—C2	120.2 (3)	H8A—C8—H8B	109.5
C4—C3—H3	119.9	N2—C8—H8C	109.5
C2—C3—H3	119.9	H8A—C8—H8C	109.5
C5—C4—C3	120.2 (2)	H8B—C8—H8C	109.5
C5—C4—H4	119.9
C7—N1—C1—C2	−112.2 (2)	C2—C1—C6—C5	0.1 (3)
C7—N1—C1—C6	70.3 (3)	N1—C1—C6—C5	177.57 (19)
C6—C1—C2—C3	−0.1 (3)	C4—C5—C6—C1	0.2 (3)
N1—C1—C2—C3	−177.7 (2)	C8—N2—C7—N1	−179.8 (2)
C1—C2—C3—C4	−0.1 (4)	C8—N2—C7—S1	0.4 (3)
C2—C3—C4—C5	0.4 (4)	C1—N1—C7—N2	−1.9 (3)
C3—C4—C5—C6	−0.4 (4)	C1—N1—C7—S1	177.91 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.81 (2)	2.55 (2)	3.351 (2)	169 (2)
N2—H2···S1ii	0.77 (2)	2.78 (2)	3.4229 (19)	142 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.81 (2)	2.55 (2)	3.351 (2)	169 (2)
N2—H2⋯S1ii	0.77 (2)	2.78 (2)	3.4229 (19)	142 (2)

Symmetry codes: (i) ; (ii) .