1-(2-Hy-droxy-eth-yl)-3-phenyl-thio-urea.

The title compound, C(9)H(12)N(2)OS, was obtained unexpectedly in a multicomponent reaction of an equimolar ratio of phenyl isothio-cyanate, malononitrile and amino-ethanol. The -C(H(2))-N(H)-(C=S)-N(H)- methyl-thio-urea-methane group is almost normal to the phenyl ring, with a dihedral angle of 71.13 (9)°. The N-C-C-O torsion angle is 72.8 (2)°. In the crystal, mol-ecules are connected by N-H⋯O, O-H⋯S and N-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of thio­ureas, see: Kilcigil & Altanlar (2006 ▶); Struga et al. (2007 ▶); Desai et al. (2007 ▶); Patel et al. (2007 ▶); Arslan et al. (2006 ▶); Katritzky & Gordeev (1991 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C9H12N2OS

M = 196.28

Tetragonal,

a = 26.170 (4) Å

c = 5.7775 (16) Å

V = 3956.8 (16) Å3

Z = 16

Mo Kα radiation

μ = 0.29 mm−1

T = 150 K

0.27 × 0.09 × 0.08 mm

Data collection

Bruker APEX 2K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.926, T max = 0.977

15367 measured reflections

2056 independent reflections

1540 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.110

S = 0.98

2056 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201183X/rk2342sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201183X/rk2342Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201183X/rk2342Isup3.cml

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

C9H12N2OS	Dx = 1.318 Mg m−3
Mr = 196.28	Melting point: 393 K
Tetragonal, I41/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4ad	Cell parameters from 800 reflections
a = 26.170 (4) Å	θ = 3.5–28.2°
c = 5.7775 (16) Å	µ = 0.29 mm−1
V = 3956.8 (16) Å3	T = 150 K
Z = 16	Needle, colourless
F(000) = 1664	0.27 × 0.09 × 0.08 mm

Bruker APEX 2K CCD diffractometer	2056 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
φ and ω scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→32
Tmin = 0.926, Tmax = 0.977	k = −32→32
15367 measured reflections	l = −7→7

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3
2056 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All s.u.'s are estimated from the variances of the (full) variance-covariance matrix. The cell s.u.'s are taken into account in the estimation of distances, angles and torsion angles.

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor 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	0.53773 (2)	0.07294 (2)	0.52460 (10)	0.0281 (2)
O1	0.56205 (6)	0.17228 (6)	−0.1675 (3)	0.0322 (5)
N1	0.45696 (7)	0.04810 (6)	0.2790 (3)	0.0269 (6)
N2	0.49000 (6)	0.12770 (6)	0.1987 (3)	0.0215 (5)
C1	0.41711 (9)	0.01902 (9)	−0.0757 (4)	0.0352 (8)
C2	0.37649 (9)	0.01894 (10)	−0.2287 (4)	0.0416 (9)
C3	0.33488 (9)	0.04979 (9)	−0.1906 (4)	0.0365 (8)
C4	0.33371 (9)	0.08094 (10)	−0.0010 (4)	0.0394 (9)
C5	0.37390 (9)	0.08096 (9)	0.1544 (4)	0.0346 (8)
C6	0.41558 (8)	0.05020 (8)	0.1157 (4)	0.0237 (7)
C7	0.49204 (8)	0.08449 (8)	0.3204 (4)	0.0216 (7)
C8	0.52638 (8)	0.16964 (8)	0.2207 (4)	0.0231 (7)
C9	0.57332 (8)	0.16375 (9)	0.0697 (4)	0.0282 (7)
H1	0.44530	−0.00190	−0.10200	0.0420*
H1A	0.45960	0.02050	0.35900	0.0320*
H1B	0.55420	0.14510	−0.22890	0.0480*
H2	0.37740	−0.00210	−0.35820	0.0500*
H2A	0.46550	0.13110	0.10050	0.0260*
H3	0.30760	0.04950	−0.29360	0.0440*
H4	0.30580	0.10220	0.02370	0.0470*
H5	0.37270	0.10170	0.28490	0.0410*
H8A	0.53710	0.17210	0.38100	0.0280*
H8B	0.50930	0.20130	0.18060	0.0280*
H9A	0.59920	0.18790	0.11950	0.0340*
H9B	0.58700	0.12960	0.08840	0.0340*

	U11	U22	U33	U12	U13	U23
S1	0.0314 (3)	0.0206 (3)	0.0322 (3)	−0.0001 (2)	−0.0121 (3)	0.0010 (2)
O1	0.0448 (10)	0.0284 (9)	0.0234 (9)	−0.0100 (8)	0.0032 (8)	−0.0016 (7)
N1	0.0285 (10)	0.0191 (9)	0.0332 (11)	−0.0045 (8)	−0.0107 (8)	0.0074 (8)
N2	0.0214 (9)	0.0219 (9)	0.0211 (10)	−0.0023 (7)	−0.0036 (7)	0.0015 (7)
C1	0.0253 (12)	0.0417 (15)	0.0385 (14)	0.0047 (11)	−0.0008 (11)	−0.0120 (12)
C2	0.0388 (15)	0.0516 (16)	0.0343 (15)	0.0003 (12)	−0.0058 (12)	−0.0151 (12)
C3	0.0292 (13)	0.0402 (15)	0.0402 (15)	−0.0034 (11)	−0.0118 (11)	0.0027 (12)
C4	0.0291 (13)	0.0384 (14)	0.0508 (17)	0.0090 (11)	−0.0089 (12)	−0.0073 (12)
C5	0.0362 (14)	0.0298 (13)	0.0377 (15)	0.0049 (11)	−0.0063 (11)	−0.0102 (11)
C6	0.0233 (11)	0.0201 (11)	0.0278 (12)	−0.0053 (9)	−0.0038 (9)	0.0052 (9)
C7	0.0233 (11)	0.0191 (11)	0.0223 (12)	0.0014 (9)	0.0007 (9)	−0.0033 (9)
C8	0.0291 (12)	0.0188 (11)	0.0214 (12)	−0.0039 (9)	−0.0015 (9)	−0.0001 (9)
C9	0.0267 (12)	0.0325 (13)	0.0255 (13)	−0.0068 (10)	−0.0002 (10)	−0.0011 (10)

S1—C7	1.707 (2)	C4—C5	1.383 (3)
O1—C9	1.420 (3)	C5—C6	1.374 (3)
O1—H1B	0.8200	C8—C9	1.515 (3)
N1—C6	1.437 (3)	C1—H1	0.9300
N1—C7	1.344 (3)	C2—H2	0.9300
N2—C7	1.333 (3)	C3—H3	0.9300
N2—C8	1.459 (3)	C4—H4	0.9300
N1—H1A	0.8600	C5—H5	0.9300
N2—H2A	0.8600	C8—H8A	0.9700
C1—C2	1.383 (3)	C8—H8B	0.9700
C1—C6	1.375 (3)	C9—H9A	0.9700
C2—C3	1.373 (3)	C9—H9B	0.9700
C3—C4	1.366 (3)
C9—O1—H1B	109.00	C2—C1—H1	120.00
C6—N1—C7	127.18 (17)	C6—C1—H1	120.00
C7—N2—C8	124.50 (17)	C1—C2—H2	120.00
C6—N1—H1A	116.00	C3—C2—H2	120.00
C7—N1—H1A	116.00	C2—C3—H3	120.00
C8—N2—H2A	118.00	C4—C3—H3	120.00
C7—N2—H2A	118.00	C3—C4—H4	120.00
C2—C1—C6	119.5 (2)	C5—C4—H4	120.00
C1—C2—C3	120.4 (2)	C4—C5—H5	120.00
C2—C3—C4	119.8 (2)	C6—C5—H5	120.00
C3—C4—C5	120.3 (2)	N2—C8—H8A	109.00
C4—C5—C6	119.9 (2)	N2—C8—H8B	109.00
N1—C6—C1	118.90 (19)	C9—C8—H8A	109.00
C1—C6—C5	120.1 (2)	C9—C8—H8B	109.00
N1—C6—C5	120.9 (2)	H8A—C8—H8B	108.00
S1—C7—N1	118.42 (16)	O1—C9—H9A	109.00
N1—C7—N2	118.68 (19)	O1—C9—H9B	109.00
S1—C7—N2	122.89 (16)	C8—C9—H9A	109.00
N2—C8—C9	113.75 (18)	C8—C9—H9B	109.00
O1—C9—C8	111.81 (17)	H9A—C9—H9B	108.00
C6—N1—C7—S1	179.93 (17)	C2—C1—C6—N1	177.1 (2)
C7—N1—C6—C1	111.2 (3)	C2—C1—C6—C5	0.1 (3)
C7—N1—C6—C5	−71.9 (3)	C1—C2—C3—C4	0.3 (4)
C6—N1—C7—N2	−0.8 (3)	C2—C3—C4—C5	−1.0 (4)
C7—N2—C8—C9	86.7 (3)	C3—C4—C5—C6	1.2 (4)
C8—N2—C7—S1	1.1 (3)	C4—C5—C6—N1	−177.6 (2)
C8—N2—C7—N1	−178.12 (19)	C4—C5—C6—C1	−0.7 (3)
C6—C1—C2—C3	0.1 (4)	N2—C8—C9—O1	72.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.54	3.3676 (18)	163
O1—H1B···S1ii	0.82	2.40	3.2137 (18)	169
N2—H2A···O1iii	0.86	2.15	2.875 (2)	142
C8—H8A···S1	0.97	2.72	3.094 (2)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.54	3.3676 (18)	163
O1—H1B⋯S1ii	0.82	2.40	3.2137 (18)	169
N2—H2A⋯O1iii	0.86	2.15	2.875 (2)	142

Symmetry codes: (i) ; (ii) ; (iii) .