rac-5-(1-Methyl-eth-yl)-2-sulfanylidene-imidazolidin-4-one.

In the title compound, C6H10N2OS, the 2-sulfanylideneimidazolidin-4-one fragment is essentially planar (r.m.s. deviation = 0.0033 Å). In the crystal, one amino group is involved in N-H⋯O hydrogen bonding, which links pairs of mol-ecules into inversion dimers, while the other amino group generates weak N-H⋯S hydrogen bonds, which link these dimers into chains in [10-1]. The chains are further aggregated into layers parallel to the ac plane through weak C-H⋯O inter-actions.

Related literature

For the biological activity of 2-thio­hydantoin derivatives, see: Ghoneim et al. (1987 ▶); Marton et al. (1993 ▶). For the crystal structures of related compounds, see: Kunimoto et al. (2009 ▶); Ogawa et al. (2007 ▶). For details of the synthesis, see: Wang et al. (2006 ▶).

Experimental

Crystal data

C6H10N2OS

M = 158.23

Monoclinic,

a = 5.7161 (1) Å

b = 17.4091 (4) Å

c = 8.2505 (2) Å

β = 103.513 (1)°

V = 798.30 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 308 K

0.93 × 0.4 × 0.3 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.936, T max = 0.979

18741 measured reflections

3064 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.114

S = 1.02

3064 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008337/cv5395sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008337/cv5395Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008337/cv5395Isup3.cml

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

C6H10N2OS	F(000) = 336
Mr = 158.23	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 637 reflections
a = 5.7161 (1) Å	θ = 7.0–60.8°
b = 17.4091 (4) Å	µ = 0.34 mm−1
c = 8.2505 (2) Å	T = 308 K
β = 103.513 (1)°	Prism, colourless
V = 798.30 (3) Å3	0.93 × 0.4 × 0.3 mm
Z = 4

Bruker APEXII CCD diffractometer	2544 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.020
φ and ω scans	θmax = 34.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −9→8
Tmin = 0.936, Tmax = 0.979	k = −26→27
18741 measured reflections	l = −12→13
3064 independent reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.0869P] where P = (Fo2 + 2Fc2)/3
3064 reflections	(Δ/σ)max = 0.002
93 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.50440 (6)	0.579973 (16)	0.22144 (4)	0.04944 (11)
C1	0.31293 (17)	0.50804 (5)	0.22060 (11)	0.03529 (18)
N1	0.25674 (18)	0.45108 (5)	0.11098 (10)	0.0431 (2)
H1	0.3188	0.446	0.0262	0.052*
C3	0.07920 (18)	0.39803 (6)	0.14899 (11)	0.03667 (18)
H3	−0.0682	0.4005	0.0602	0.044*
C4	0.16814 (19)	0.31474 (5)	0.16973 (13)	0.0415 (2)
H4	0.2276	0.3015	0.0711	0.05*
C5	−0.0352 (2)	0.25955 (7)	0.17693 (18)	0.0568 (3)
H5A	−0.0905	0.2689	0.2764	0.085*
H5B	0.0219	0.2077	0.1778	0.085*
H5C	−0.1655	0.2672	0.0811	0.085*
C6	0.3773 (2)	0.30522 (7)	0.3219 (2)	0.0595 (3)
H6C	0.5011	0.3417	0.3163	0.089*
H6B	0.4408	0.2541	0.3236	0.089*
H6A	0.3215	0.3139	0.4214	0.089*
C2	0.03374 (17)	0.43453 (5)	0.30588 (12)	0.03636 (18)
O1	−0.10205 (16)	0.41213 (5)	0.38922 (12)	0.0516 (2)
N2	0.17754 (15)	0.49851 (5)	0.33699 (11)	0.03987 (18)
H2	0.1825	0.5291	0.4196	0.048*

	U11	U22	U33	U12	U13	U23
S1	0.0669 (2)	0.04239 (16)	0.04620 (17)	−0.02026 (11)	0.02773 (13)	−0.00744 (10)
C1	0.0445 (4)	0.0311 (4)	0.0333 (4)	−0.0024 (3)	0.0153 (3)	0.0008 (3)
N1	0.0626 (5)	0.0386 (4)	0.0348 (4)	−0.0127 (4)	0.0248 (4)	−0.0050 (3)
C3	0.0431 (4)	0.0368 (4)	0.0320 (4)	−0.0061 (3)	0.0126 (3)	−0.0032 (3)
C4	0.0497 (5)	0.0335 (4)	0.0486 (5)	−0.0080 (4)	0.0263 (4)	−0.0118 (4)
C5	0.0625 (7)	0.0448 (6)	0.0676 (7)	−0.0212 (5)	0.0242 (6)	−0.0143 (5)
C6	0.0440 (5)	0.0419 (5)	0.0917 (10)	0.0023 (4)	0.0142 (6)	0.0060 (6)
C2	0.0379 (4)	0.0328 (4)	0.0431 (4)	−0.0009 (3)	0.0190 (3)	−0.0048 (3)
O1	0.0562 (5)	0.0449 (4)	0.0667 (5)	−0.0122 (3)	0.0406 (4)	−0.0155 (4)
N2	0.0486 (4)	0.0345 (4)	0.0431 (4)	−0.0074 (3)	0.0239 (3)	−0.0096 (3)

S1—C1	1.6621 (9)	C4—H4	0.98
C1—N1	1.3300 (12)	C5—H5A	0.96
C1—N2	1.3769 (12)	C5—H5B	0.96
N1—C3	1.4595 (12)	C5—H5C	0.96
N1—H1	0.86	C6—H6C	0.96
C3—C2	1.5179 (13)	C6—H6B	0.96
C3—C4	1.5328 (14)	C6—H6A	0.96
C3—H3	0.98	C2—O1	1.2152 (12)
C4—C5	1.5200 (14)	C2—N2	1.3724 (12)
C4—C6	1.5269 (18)	N2—H2	0.86
N1—C1—N2	107.37 (8)	C4—C5—H5A	109.5
N1—C1—S1	128.23 (7)	C4—C5—H5B	109.5
N2—C1—S1	124.39 (7)	H5A—C5—H5B	109.5
C1—N1—C3	113.28 (8)	C4—C5—H5C	109.5
C1—N1—H1	123.4	H5A—C5—H5C	109.5
C3—N1—H1	123.4	H5B—C5—H5C	109.5
N1—C3—C2	100.63 (7)	C4—C6—H6C	109.5
N1—C3—C4	113.17 (8)	C4—C6—H6B	109.5
C2—C3—C4	114.79 (8)	H6C—C6—H6B	109.5
N1—C3—H3	109.3	C4—C6—H6A	109.5
C2—C3—H3	109.3	H6C—C6—H6A	109.5
C4—C3—H3	109.3	H6B—C6—H6A	109.5
C5—C4—C6	111.00 (10)	O1—C2—N2	126.04 (9)
C5—C4—C3	111.44 (9)	O1—C2—C3	127.40 (9)
C6—C4—C3	111.72 (8)	N2—C2—C3	106.55 (8)
C5—C4—H4	107.5	C2—N2—C1	112.15 (8)
C6—C4—H4	107.5	C2—N2—H2	123.9
C3—C4—H4	107.5	C1—N2—H2	123.9
N2—C1—N1—C3	−0.87 (12)	N1—C3—C2—O1	−179.83 (11)
S1—C1—N1—C3	−179.62 (7)	C4—C3—C2—O1	−57.99 (15)
C1—N1—C3—C2	0.55 (11)	N1—C3—C2—N2	−0.03 (10)
C1—N1—C3—C4	−122.43 (10)	C4—C3—C2—N2	121.82 (9)
N1—C3—C4—C5	−169.42 (9)	O1—C2—N2—C1	179.33 (11)
C2—C3—C4—C5	75.83 (11)	C3—C2—N2—C1	−0.49 (11)
N1—C3—C4—C6	65.78 (11)	N1—C1—N2—C2	0.84 (12)
C2—C3—C4—C6	−48.97 (12)	S1—C1—N2—C2	179.65 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	2.02	2.8573 (11)	164
N1—H1···S1ii	0.86	2.52	3.3806 (9)	176
C6—H6C···O1iii	0.96	2.52	3.4434 (14)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	2.02	2.8573 (11)	164
N1—H1⋯S1ii	0.86	2.52	3.3806 (9)	176
C6—H6C⋯O1iii	0.96	2.52	3.4434 (14)	160

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