5-Isopropyl-5-methyl-2-sulfanylidene-imidazolidin-4-one.

In the title compound, C7H12N2OS, the 2-sulfanylideneimidazolidin-4-one moiety is nearly planar, with a maximum deviation of 0.054 (2) Å. In the crystal, a pair of N-H⋯O hydrogen bonds and a pair of N-H⋯S hydrogen bonds each form a centrosymmetric ring with an R 2 (2)(8) graph-set motif. The enanti-omeric R and S mol-ecules are alternately linked into a tape along [1-10] via these pairs of hydrogen bonds.

Related literature

For applications and the biological activity of 2-sulfanylideneimidazolidin-4-ones, see: Marton et al. (1993 ▶). For the crystal structures of related compounds, see: Devillanova et al. (1987 ▶); Ogawa et al. (2009 ▶); Walker et al. (1969 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶). For the synthetic procedure, see: Wang et al. (2006 ▶).

Experimental

Crystal data

C7H12N2OS

M = 172.26

Monoclinic,

a = 5.8317 (5) Å

b = 9.2114 (8) Å

c = 16.8967 (16) Å

β = 95.855 (3)°

V = 902.92 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 123 K

0.20 × 0.10 × 0.04 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Rigaku, 1998 ▶) T min = 0.795, T max = 0.988

9484 measured reflections

2051 independent reflections

1660 reflections with F 2 > 2σ(F 2)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.126

S = 1.14

2051 reflections

111 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013639/is5273sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013639/is5273Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013639/is5273Isup3.cml

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

C7H12N2OS	F(000) = 368
Mr = 172.26	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 2692 reflections
a = 5.8317 (5) Å	θ = 3.5–27.5°
b = 9.2114 (8) Å	µ = 0.31 mm−1
c = 16.8967 (16) Å	T = 123 K
β = 95.855 (3)°	Plate, colorless
V = 902.92 (14) Å3	0.20 × 0.10 × 0.04 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	1660 reflections with F2 > 2σ(F2)
Detector resolution: 7.314 pixels mm-1	Rint = 0.038
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −7→7
Tmin = 0.795, Tmax = 0.988	k = −11→10
9484 measured reflections	l = −21→21
2051 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0462P)2 + 1.0263P] where P = (Fo2 + 2Fc2)/3
2051 reflections	(Δ/σ)max < 0.001
111 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods

Experimental. m.p. 145 °C; 1H NMR (500 MHz, CDCl3): δ 9.11 (br s, 1H), 8.09 (br s, 1H), 2.07 (sep, 1H, J = 6.9 Hz), 1.46 (s, 3H), 1.03 (d, 3H, J = 6.9 Hz), 0.95 (d, 3H, J = 6.9 Hz); 13C NMR (125 MHz, CDCl3): δ 181.13, 177.71, 70.15, 34.82, 20.97, 16.86, 16.42; IR (KBr, cm-1): 3182 (ν(N—H)), 1743 (ν(C═O)), 1532 (ν(C—N)+δ(N—H)).

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
S1	−0.05936 (9)	0.28891 (6)	0.42364 (3)	0.02414 (18)
O1	0.6264 (3)	0.09152 (17)	0.58845 (10)	0.0278 (4)
N1	0.2019 (4)	0.3572 (2)	0.55956 (10)	0.0204 (4)
N2	0.3053 (4)	0.1562 (2)	0.50439 (11)	0.0244 (5)
C1	0.1488 (4)	0.2702 (3)	0.49775 (12)	0.0192 (5)
C2	0.4673 (4)	0.1723 (3)	0.56850 (13)	0.0219 (5)
C3	0.4068 (4)	0.3105 (3)	0.61121 (12)	0.0190 (5)
C4	0.6026 (4)	0.4209 (3)	0.61059 (14)	0.0259 (5)
C5	0.3484 (4)	0.2730 (3)	0.69649 (12)	0.0225 (5)
C6	0.1683 (5)	0.1524 (3)	0.69600 (14)	0.0300 (6)
C7	0.2715 (5)	0.4046 (3)	0.74022 (15)	0.0331 (6)
H1	0.140 (5)	0.431 (4)	0.5650 (16)	0.026 (7)*
H2	0.320 (6)	0.086 (4)	0.468 (2)	0.049 (9)*
H4A	0.7335	0.3896	0.6476	0.0310*
H4B	0.5490	0.5161	0.6269	0.0310*
H4C	0.6506	0.4277	0.5568	0.0310*
H5	0.4929	0.2361	0.7268	0.0270*
H6A	0.2276	0.0643	0.6726	0.0360*
H6B	0.0265	0.1833	0.6644	0.0360*
H6C	0.1355	0.1321	0.7507	0.0360*
H7A	0.1359	0.4476	0.7100	0.0397*
H7B	0.3966	0.4761	0.7460	0.0397*
H7C	0.2323	0.3755	0.7930	0.0397*

	U11	U22	U33	U12	U13	U23
S1	0.0281 (3)	0.0216 (3)	0.0209 (3)	0.0062 (3)	−0.0060 (2)	−0.0030 (2)
O1	0.0281 (9)	0.0245 (9)	0.0290 (9)	0.0104 (7)	−0.0057 (7)	−0.0047 (7)
N1	0.0255 (10)	0.0156 (9)	0.0193 (9)	0.0067 (8)	−0.0011 (7)	−0.0018 (7)
N2	0.0315 (11)	0.0185 (9)	0.0219 (10)	0.0086 (8)	−0.0039 (8)	−0.0053 (8)
C1	0.0223 (10)	0.0177 (10)	0.0171 (10)	0.0037 (8)	0.0005 (8)	0.0013 (8)
C2	0.0245 (11)	0.0192 (11)	0.0212 (11)	0.0008 (9)	−0.0016 (8)	−0.0017 (8)
C3	0.0205 (10)	0.0178 (10)	0.0179 (10)	0.0024 (8)	−0.0017 (8)	−0.0007 (8)
C4	0.0254 (11)	0.0231 (11)	0.0286 (12)	−0.0014 (9)	0.0001 (9)	−0.0003 (9)
C5	0.0223 (11)	0.0258 (11)	0.0188 (10)	−0.0012 (9)	−0.0004 (8)	0.0001 (9)
C6	0.0306 (12)	0.0296 (13)	0.0295 (12)	−0.0072 (10)	0.0010 (10)	0.0047 (10)
C7	0.0376 (14)	0.0332 (14)	0.0286 (13)	0.0006 (11)	0.0035 (10)	−0.0060 (10)

S1—C1	1.662 (2)	N2—H2	0.91 (4)
O1—C2	1.210 (3)	C4—H4A	0.980
N1—C1	1.328 (3)	C4—H4B	0.980
N1—C3	1.470 (3)	C4—H4C	0.980
N2—C1	1.389 (3)	C5—H5	1.000
N2—C2	1.371 (3)	C6—H6A	0.980
C2—C3	1.523 (3)	C6—H6B	0.980
C3—C4	1.529 (3)	C6—H6C	0.980
C3—C5	1.553 (3)	C7—H7A	0.980
C5—C6	1.528 (4)	C7—H7B	0.980
C5—C7	1.512 (4)	C7—H7C	0.980
N1—H1	0.78 (3)
C1—N1—C3	113.63 (18)	C3—C4—H4A	109.471
C1—N2—C2	112.12 (18)	C3—C4—H4B	109.469
S1—C1—N1	128.62 (17)	C3—C4—H4C	109.469
S1—C1—N2	124.27 (16)	H4A—C4—H4B	109.470
N1—C1—N2	107.11 (18)	H4A—C4—H4C	109.476
O1—C2—N2	126.9 (2)	H4B—C4—H4C	109.473
O1—C2—C3	126.2 (2)	C3—C5—H5	107.349
N2—C2—C3	106.89 (18)	C6—C5—H5	107.356
N1—C3—C2	100.18 (16)	C7—C5—H5	107.359
N1—C3—C4	111.34 (17)	C5—C6—H6A	109.476
N1—C3—C5	111.94 (17)	C5—C6—H6B	109.471
C2—C3—C4	110.09 (18)	C5—C6—H6C	109.465
C2—C3—C5	109.67 (18)	H6A—C6—H6B	109.480
C4—C3—C5	112.89 (17)	H6A—C6—H6C	109.472
C3—C5—C6	111.88 (17)	H6B—C6—H6C	109.463
C3—C5—C7	112.26 (19)	C5—C7—H7A	109.475
C6—C5—C7	110.4 (2)	C5—C7—H7B	109.480
C1—N1—H1	123.2 (19)	C5—C7—H7C	109.472
C3—N1—H1	122.7 (19)	H7A—C7—H7B	109.474
C1—N2—H2	126 (2)	H7A—C7—H7C	109.465
C2—N2—H2	121 (2)	H7B—C7—H7C	109.461
C1—N1—C3—C2	−1.1 (3)	O1—C2—C3—C5	−61.8 (3)
C1—N1—C3—C4	115.27 (19)	N2—C2—C3—N1	−0.6 (2)
C1—N1—C3—C5	−117.31 (18)	N2—C2—C3—C4	−117.96 (18)
C3—N1—C1—S1	−176.53 (17)	N2—C2—C3—C5	117.24 (18)
C3—N1—C1—N2	2.4 (3)	N1—C3—C5—C6	58.7 (3)
C1—N2—C2—O1	−178.9 (2)	N1—C3—C5—C7	−66.0 (2)
C1—N2—C2—C3	2.1 (3)	C2—C3—C5—C6	−51.5 (2)
C2—N2—C1—S1	176.16 (17)	C2—C3—C5—C7	−176.24 (15)
C2—N2—C1—N1	−2.9 (3)	C4—C3—C5—C6	−174.68 (16)
O1—C2—C3—N1	−179.6 (2)	C4—C3—C5—C7	60.6 (3)
O1—C2—C3—C4	63.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1i	0.78 (3)	2.63 (3)	3.383 (2)	162 (3)
N2—H2···O1ii	0.91 (4)	1.93 (4)	2.820 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1i	0.78 (3)	2.63 (3)	3.383 (2)	162 (3)
N2—H2⋯O1ii	0.91 (4)	1.93 (4)	2.820 (3)	166 (3)

Symmetry codes: (i) ; (ii) .