N-Propionylthio-urea.

The mol-ecule of the title compound, C(4)H(8)N(2)OS, is essentially planar; it adopts a trans configuration with respect to the position of the propionyl group relative to the thiono S atom about the C-N bond. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond between the propionyl O atom and the amide H atom. Mol-ecules are linked into a two-dimensional network parallel to the (10) plane by N-H⋯O and N-H⋯S inter-molecular hydrogen bonds.

Related literature

For the crystal structures of thio­urea analogues, see: Yusof et al. (2007 ▶); Rosli et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C4H8N2OS

M = 132.19

Monoclinic,

a = 5.0790 (15) Å

b = 14.342 (4) Å

c = 9.273 (3) Å

β = 102.744 (6)°

V = 658.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 298 (2) K

0.48 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.832, T max = 0.946

3622 measured reflections

1291 independent reflections

910 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.02

1291 reflections

73 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706031X/ci2516sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706031X/ci2516Isup2.hkl

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

C4H8N2OS	F000 = 280
Mr = 132.19	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1291 reflections
a = 5.0790 (15) Å	θ = 2.6–26.0º
b = 14.342 (4) Å	µ = 0.40 mm−1
c = 9.273 (3) Å	T = 298 (2) K
β = 102.744 (6)º	Block, yellow
V = 658.8 (3) Å3	0.48 × 0.19 × 0.14 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1291 independent reflections
Radiation source: fine-focus sealed tube	910 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 83.66 pixels mm-1	θmax = 26.0º
T = 298(2) K	θmin = 2.6º
ω scan	h = −6→5
Absorption correction: multi-scan(SADABS; Bruker, 2000)	k = −16→17
Tmin = 0.832, Tmax = 0.946	l = −9→11
3622 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.293P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
1291 reflections	Δρmax = 0.23 e Å−3
73 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 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 > σ(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	0.01989 (18)	0.06361 (6)	0.28118 (8)	0.0646 (3)
O1	0.7005 (4)	0.22101 (13)	0.58191 (18)	0.0537 (5)
N1	0.4084 (4)	0.18551 (14)	0.3657 (2)	0.0428 (6)
H1D	0.3630	0.2009	0.2739	0.051*
C4	0.2638 (5)	0.11286 (17)	0.4084 (3)	0.0413 (6)
N2	0.3300 (5)	0.08712 (15)	0.5470 (2)	0.0514 (6)
H2C	0.4587	0.1151	0.6072	0.062*
H2D	0.2448	0.0422	0.5779	0.062*
C3	0.6154 (5)	0.23647 (18)	0.4506 (3)	0.0431 (6)
C2	0.7271 (7)	0.3102 (2)	0.3675 (3)	0.0635 (9)
H2A	0.7959	0.2807	0.2892	0.076*
H2B	0.5808	0.3512	0.3212	0.076*
C1	0.9454 (7)	0.3677 (2)	0.4578 (3)	0.0706 (9)
H1A	1.0051	0.4130	0.3958	0.106*
H1B	1.0940	0.3282	0.5022	0.106*
H1C	0.8785	0.3990	0.5340	0.106*

	U11	U22	U33	U12	U13	U23
S1	0.0696 (6)	0.0701 (6)	0.0465 (5)	−0.0255 (4)	−0.0038 (4)	0.0050 (4)
O1	0.0653 (13)	0.0566 (12)	0.0324 (10)	−0.0098 (10)	−0.0040 (8)	0.0002 (8)
N1	0.0498 (14)	0.0479 (13)	0.0273 (10)	−0.0060 (11)	0.0013 (9)	0.0028 (9)
C4	0.0445 (15)	0.0408 (15)	0.0385 (14)	0.0040 (12)	0.0089 (11)	−0.0008 (11)
N2	0.0633 (16)	0.0523 (14)	0.0357 (12)	−0.0122 (12)	0.0045 (10)	0.0034 (10)
C3	0.0473 (17)	0.0420 (15)	0.0373 (14)	0.0028 (12)	0.0032 (11)	−0.0015 (11)
C2	0.073 (2)	0.063 (2)	0.0484 (17)	−0.0223 (17)	−0.0002 (15)	0.0073 (14)
C1	0.076 (2)	0.069 (2)	0.064 (2)	−0.0238 (18)	0.0095 (17)	−0.0026 (16)

S1—C4	1.668 (3)	C3—C2	1.492 (4)
O1—C3	1.219 (3)	C2—C1	1.483 (4)
N1—C3	1.377 (3)	C2—H2A	0.97
N1—C4	1.382 (3)	C2—H2B	0.97
N1—H1D	0.86	C1—H1A	0.96
C4—N2	1.308 (3)	C1—H1B	0.96
N2—H2C	0.86	C1—H1C	0.96
N2—H2D	0.86
C3—N1—C4	128.6 (2)	C1—C2—C3	115.1 (2)
C3—N1—H1D	115.7	C1—C2—H2A	108.5
C4—N1—H1D	115.7	C3—C2—H2A	108.5
N2—C4—N1	117.2 (2)	C1—C2—H2B	108.5
N2—C4—S1	124.4 (2)	C3—C2—H2B	108.5
N1—C4—S1	118.37 (18)	H2A—C2—H2B	107.5
C4—N2—H2C	120.0	C2—C1—H1A	109.5
C4—N2—H2D	120.0	C2—C1—H1B	109.5
H2C—N2—H2D	120.0	H1A—C1—H1B	109.5
O1—C3—N1	122.2 (2)	C2—C1—H1C	109.5
O1—C3—C2	123.6 (2)	H1A—C1—H1C	109.5
N1—C3—C2	114.2 (2)	H1B—C1—H1C	109.5
C3—N1—C4—N2	−0.7 (4)	C4—N1—C3—C2	179.8 (3)
C3—N1—C4—S1	179.7 (2)	O1—C3—C2—C1	−2.5 (5)
C4—N1—C3—O1	0.7 (4)	N1—C3—C2—C1	178.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O1	0.86	2.00	2.658 (3)	133
N1—H1D···O1i	0.86	2.11	2.935 (3)	160
N2—H2D···S1ii	0.86	2.57	3.409 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2C⋯O1	0.86	2.00	2.658 (3)	133
N1—H1D⋯O1i	0.86	2.11	2.935 (3)	160
N2—H2D⋯S1ii	0.86	2.57	3.409 (3)	166

Symmetry codes: (i) ; (ii) .