Cinnamoyl-thio-urea.

IN THE TITLE COMPOUND [SYSTEMATIC NAME: 1-(3-phenyl-prop-2-eno-yl)thio-urea], C(10)H(10)N(2)OS, the acetyl-thio-urea fragment and the phenyl ring adopt an E configuration. The roughly planar but-2-enoyl-thio-urea fragment [maximum deviation = 0.053 (3) Å] forms a dihedral of 10.54 (11)° with the phenyl ring. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked into sheets parallel to (100) by N-H⋯S hydrogen bonds.

Related literature

For the preparation, see: Hassan et al. (2010a ▶). For related structures, see: Hung et al. (2010 ▶); Hassan et al. (2008 ▶, 2009 ▶, 2010 ▶); Yamin & Hassan (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H10N2OS

M = 206.26

Monoclinic,

a = 14.3313 (18) Å

b = 4.9801 (6) Å

c = 15.4199 (19) Å

β = 111.612 (3)°

V = 1023.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 273 K

0.34 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.960, T max = 0.975

7192 measured reflections

2551 independent reflections

1688 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.156

S = 1.08

2551 reflections

127 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040018/ci5180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040018/ci5180Isup2.hkl

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

C10H10N2OS	F(000) = 432
Mr = 206.26	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1059 reflections
a = 14.3313 (18) Å	θ = 1.5–28.3°
b = 4.9801 (6) Å	µ = 0.28 mm−1
c = 15.4199 (19) Å	T = 273 K
β = 111.612 (3)°	Plate, colourless
V = 1023.2 (2) Å3	0.34 × 0.12 × 0.09 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2551 independent reflections
Radiation source: fine-focus sealed tube	1688 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −18→19
Tmin = 0.960, Tmax = 0.975	k = −6→6
7192 measured reflections	l = −20→16

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.1088P] where P = (Fo2 + 2Fc2)/3
2551 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.40 e Å−3
3 restraints	Δρmin = −0.20 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.

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	−0.03467 (5)	0.16643 (15)	0.35571 (4)	0.0559 (3)
O1	0.24962 (15)	0.6309 (4)	0.51663 (12)	0.0647 (6)
N1	0.11111 (14)	0.5226 (4)	0.38961 (13)	0.0428 (5)
H1A	0.0790	0.5740	0.3339	0.051*
N2	0.11216 (16)	0.2739 (5)	0.51525 (14)	0.0551 (6)
H2A	0.1680	0.3641	0.5479	0.066*
H2B	0.0850	0.1571	0.5415	0.066*
C1	0.2743 (2)	1.2916 (6)	0.26352 (19)	0.0553 (7)
H1B	0.2112	1.2149	0.2350	0.066*
C2	0.3067 (2)	1.4824 (6)	0.2166 (2)	0.0674 (8)
H2C	0.2655	1.5331	0.1567	0.081*
C3	0.3993 (2)	1.5982 (6)	0.2575 (2)	0.0676 (8)
H3A	0.4206	1.7273	0.2253	0.081*
C4	0.4604 (2)	1.5251 (6)	0.3454 (2)	0.0669 (8)
H4A	0.5232	1.6043	0.3731	0.080*
C5	0.42846 (19)	1.3317 (6)	0.3932 (2)	0.0551 (7)
H5A	0.4704	1.2819	0.4530	0.066*
C6	0.33484 (18)	1.2118 (5)	0.35306 (17)	0.0431 (6)
C7	0.30347 (18)	1.0120 (5)	0.40557 (17)	0.0456 (6)
H7A	0.3462	0.9838	0.4670	0.055*
C8	0.22069 (18)	0.8664 (5)	0.37521 (16)	0.0434 (6)
H8A	0.1758	0.8900	0.3143	0.052*
C9	0.19735 (18)	0.6684 (5)	0.43484 (16)	0.0433 (6)
C10	0.06860 (17)	0.3267 (5)	0.42595 (15)	0.0395 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0556 (4)	0.0654 (5)	0.0402 (4)	−0.0166 (3)	0.0101 (3)	0.0071 (3)
O1	0.0744 (13)	0.0688 (13)	0.0390 (10)	−0.0198 (10)	0.0072 (9)	0.0076 (9)
N1	0.0475 (11)	0.0421 (11)	0.0342 (10)	−0.0031 (9)	0.0097 (9)	0.0060 (9)
N2	0.0651 (14)	0.0608 (15)	0.0354 (11)	−0.0148 (11)	0.0139 (10)	0.0072 (10)
C1	0.0558 (15)	0.0559 (17)	0.0509 (15)	−0.0097 (13)	0.0160 (13)	0.0026 (13)
C2	0.077 (2)	0.065 (2)	0.0623 (18)	−0.0090 (17)	0.0280 (16)	0.0113 (16)
C3	0.081 (2)	0.0569 (18)	0.083 (2)	−0.0114 (16)	0.0516 (19)	0.0027 (17)
C4	0.0598 (17)	0.0601 (19)	0.092 (2)	−0.0174 (15)	0.0407 (18)	−0.0169 (18)
C5	0.0523 (15)	0.0526 (16)	0.0576 (17)	−0.0040 (13)	0.0170 (13)	−0.0088 (14)
C6	0.0444 (12)	0.0373 (13)	0.0470 (14)	−0.0009 (10)	0.0162 (11)	−0.0036 (11)
C7	0.0488 (14)	0.0427 (14)	0.0392 (12)	−0.0002 (11)	0.0090 (11)	−0.0021 (11)
C8	0.0490 (13)	0.0410 (14)	0.0368 (12)	−0.0022 (11)	0.0117 (10)	−0.0003 (11)
C9	0.0504 (13)	0.0408 (14)	0.0369 (13)	−0.0005 (11)	0.0140 (11)	−0.0009 (11)
C10	0.0455 (12)	0.0383 (12)	0.0360 (12)	0.0041 (11)	0.0162 (10)	0.0034 (10)

S1—C10	1.679 (2)	C2—H2C	0.93
O1—C9	1.221 (3)	C3—C4	1.365 (4)
N1—C10	1.374 (3)	C3—H3A	0.93
N1—C9	1.381 (3)	C4—C5	1.389 (4)
N1—H1A	0.85	C4—H4A	0.93
N2—C10	1.312 (3)	C5—C6	1.389 (3)
N2—H2A	0.89	C5—H5A	0.93
N2—H2B	0.88	C6—C7	1.455 (3)
C1—C2	1.374 (4)	C7—C8	1.320 (3)
C1—C6	1.391 (3)	C7—H7A	0.93
C1—H1B	0.93	C8—C9	1.468 (3)
C2—C3	1.369 (4)	C8—H8A	0.93
C10—N1—C9	128.04 (19)	C6—C5—C4	121.0 (3)
C10—N1—H1A	118.0	C6—C5—H5A	119.5
C9—N1—H1A	113.7	C4—C5—H5A	119.5
C10—N2—H2A	118.2	C5—C6—C1	117.8 (2)
C10—N2—H2B	119.8	C5—C6—C7	119.5 (2)
H2A—N2—H2B	122.0	C1—C6—C7	122.7 (2)
C2—C1—C6	120.8 (3)	C8—C7—C6	126.9 (2)
C2—C1—H1B	119.6	C8—C7—H7A	116.6
C6—C1—H1B	119.6	C6—C7—H7A	116.6
C3—C2—C1	120.4 (3)	C7—C8—C9	121.9 (2)
C3—C2—H2C	119.8	C7—C8—H8A	119.0
C1—C2—H2C	119.8	C9—C8—H8A	119.0
C4—C3—C2	120.3 (3)	O1—C9—N1	122.4 (2)
C4—C3—H3A	119.9	O1—C9—C8	123.7 (2)
C2—C3—H3A	119.9	N1—C9—C8	113.9 (2)
C3—C4—C5	119.7 (3)	N2—C10—N1	117.3 (2)
C3—C4—H4A	120.1	N2—C10—S1	123.18 (19)
C5—C4—H4A	120.1	N1—C10—S1	119.49 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.89	1.95	2.649 (3)	134
N1—H1A···S1i	0.85	2.79	3.602 (2)	159
N2—H2B···S1ii	0.88	2.54	3.409 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.89	1.95	2.649 (3)	134
N1—H1A⋯S1i	0.85	2.79	3.602 (2)	159
N2—H2B⋯S1ii	0.88	2.54	3.409 (2)	169

Symmetry codes: (i) ; (ii) .