(E)-Methyl 2-(3-cinnamoyl-thio-ureido)acetate.

In the title compound, C(13)H(14)N(2)O(3)S, the methyl 2-(3-formyl-thio-ureido)acetate fragment and the phenyl ring adopt an E configuration. The mol-ecule exhibits an intra-molecular N-H⋯O hydrogen bond, which completes a six-membered ring. The crystal packing is stabilized by inter-molecular N-H⋯S contacts, generating a two-dimensional hydrogen-bonding network.

Related literature

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

Experimental

Crystal data

C13H14N2O3S

M = 278.33

Triclinic,

a = 4.992 (2) Å

b = 11.720 (5) Å

c = 12.542 (6) Å

α = 112.999 (7)°

β = 91.492 (7)°

γ = 96.258 (7)°

V = 669.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.38 × 0.32 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.912, T max = 0.969

6562 measured reflections

2466 independent reflections

1689 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.173

S = 1.12

2466 reflections

180 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.36 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/S1600536810030084/kp2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030084/kp2273Isup2.hkl

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

C13H14N2O3S	Z = 2
Mr = 278.33	F(000) = 292
Triclinic, P1	Dx = 1.381 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.992 (2) Å	Cell parameters from 1753 reflections
b = 11.720 (5) Å	θ = 1.8–25.5°
c = 12.542 (6) Å	µ = 0.25 mm−1
α = 112.999 (7)°	T = 298 K
β = 91.492 (7)°	Block, colourless
γ = 96.258 (7)°	0.38 × 0.32 × 0.13 mm
V = 669.6 (5) Å3

Bruker SMART APEX CCD area-detector diffractometer	2466 independent reflections
Radiation source: fine-focus sealed tube	1689 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scan	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −6→6
Tmin = 0.912, Tmax = 0.969	k = −14→14
6562 measured reflections	l = −15→15

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0832P)2 + 0.1736P] where P = (Fo2 + 2Fc2)/3
2466 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.36 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	0.2582 (2)	0.96891 (9)	0.84472 (8)	0.0546 (4)
O1	0.8785 (5)	1.3017 (3)	0.8950 (2)	0.0691 (9)
O2	0.6025 (5)	1.2077 (3)	0.5979 (2)	0.0728 (9)
O3	0.2006 (5)	1.1278 (2)	0.5020 (2)	0.0578 (7)
N1	0.6772 (6)	1.1430 (3)	0.9392 (2)	0.0423 (7)
N2	0.4711 (6)	1.1404 (3)	0.7718 (2)	0.0497 (8)
C1	1.5217 (7)	1.3497 (3)	1.2458 (3)	0.0541 (10)
H1B	1.4097	1.2766	1.2349	0.065*
C2	1.7365 (8)	1.3923 (4)	1.3298 (3)	0.0643 (11)
H2B	1.7663	1.3478	1.3753	0.077*
C3	1.9055 (8)	1.4992 (4)	1.3466 (3)	0.0596 (10)
H3A	2.0484	1.5274	1.4035	0.072*
C4	1.8621 (7)	1.5641 (3)	1.2790 (3)	0.0554 (10)
H4A	1.9769	1.6362	1.2891	0.066*
C5	1.6476 (7)	1.5223 (3)	1.1957 (3)	0.0477 (9)
H5A	1.6196	1.5672	1.1504	0.057*
C6	1.4733 (6)	1.4153 (3)	1.1780 (3)	0.0400 (8)
C7	1.2554 (7)	1.3734 (3)	1.0864 (3)	0.0453 (8)
H7A	1.2414	1.4237	1.0452	0.054*
C8	1.0742 (6)	1.2719 (3)	1.0546 (3)	0.0428 (8)
H8A	1.0749	1.2193	1.0942	0.051*
C9	0.8735 (7)	1.2429 (3)	0.9572 (3)	0.0479 (9)
C10	0.4759 (6)	1.0896 (3)	0.8501 (3)	0.0394 (8)
C11	0.2769 (7)	1.0976 (3)	0.6722 (3)	0.0496 (9)
H11A	0.1038	1.1253	0.6961	0.059*
H11B	0.2522	1.0070	0.6355	0.059*
C12	0.3849 (7)	1.1516 (3)	0.5889 (3)	0.0431 (8)
C13	0.2708 (9)	1.1823 (4)	0.4194 (3)	0.0680 (12)
H13A	0.1251	1.1594	0.3605	0.102*
H13B	0.4312	1.1520	0.3841	0.102*
H13C	0.3027	1.2716	0.4588	0.102*
H2A	0.591 (6)	1.204 (2)	0.787 (3)	0.076 (14)*
H1A	0.694 (8)	1.112 (3)	0.990 (3)	0.070 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0615 (6)	0.0558 (6)	0.0520 (6)	−0.0166 (4)	−0.0175 (4)	0.0350 (5)
O1	0.0748 (18)	0.0797 (19)	0.0662 (17)	−0.0313 (15)	−0.0313 (14)	0.0561 (16)
O2	0.0507 (17)	0.109 (2)	0.0733 (19)	−0.0241 (16)	−0.0172 (14)	0.0620 (18)
O3	0.0570 (15)	0.0750 (18)	0.0525 (15)	−0.0159 (13)	−0.0175 (12)	0.0450 (14)
N1	0.0475 (16)	0.0468 (17)	0.0386 (16)	−0.0049 (13)	−0.0107 (13)	0.0270 (14)
N2	0.0589 (19)	0.0551 (19)	0.0407 (16)	−0.0160 (15)	−0.0173 (14)	0.0324 (15)
C1	0.054 (2)	0.058 (2)	0.058 (2)	−0.0086 (18)	−0.0137 (18)	0.0368 (19)
C2	0.066 (3)	0.077 (3)	0.061 (2)	−0.005 (2)	−0.019 (2)	0.046 (2)
C3	0.053 (2)	0.070 (3)	0.050 (2)	−0.004 (2)	−0.0173 (18)	0.023 (2)
C4	0.050 (2)	0.048 (2)	0.061 (2)	−0.0087 (17)	−0.0087 (18)	0.0193 (19)
C5	0.051 (2)	0.047 (2)	0.051 (2)	−0.0028 (17)	−0.0041 (17)	0.0278 (18)
C6	0.0392 (18)	0.0427 (19)	0.0408 (18)	−0.0029 (15)	0.0001 (15)	0.0217 (16)
C7	0.047 (2)	0.049 (2)	0.0449 (19)	−0.0022 (17)	−0.0054 (16)	0.0267 (17)
C8	0.0451 (19)	0.050 (2)	0.0400 (19)	−0.0011 (16)	−0.0061 (15)	0.0271 (16)
C9	0.053 (2)	0.050 (2)	0.045 (2)	−0.0034 (17)	−0.0062 (17)	0.0270 (18)
C10	0.0424 (19)	0.0425 (19)	0.0379 (18)	0.0021 (15)	−0.0024 (15)	0.0221 (16)
C11	0.051 (2)	0.059 (2)	0.045 (2)	−0.0092 (18)	−0.0124 (17)	0.0330 (17)
C12	0.046 (2)	0.048 (2)	0.0401 (19)	0.0011 (17)	−0.0079 (16)	0.0246 (17)
C13	0.083 (3)	0.083 (3)	0.056 (2)	−0.009 (2)	−0.012 (2)	0.052 (2)

S1—C10	1.666 (3)	C3—H3A	0.9300
O1—C9	1.226 (4)	C4—C5	1.380 (5)
O2—C12	1.186 (4)	C4—H4A	0.9300
O3—C12	1.329 (4)	C5—C6	1.383 (4)
O3—C13	1.445 (4)	C5—H5A	0.9300
N1—C10	1.381 (4)	C6—C7	1.456 (5)
N1—C9	1.383 (4)	C7—C8	1.330 (5)
N1—H1A	0.859 (10)	C7—H7A	0.9300
N2—C10	1.333 (4)	C8—C9	1.466 (5)
N2—C11	1.447 (4)	C8—H8A	0.9300
N2—H2A	0.859 (10)	C11—C12	1.502 (4)
C1—C6	1.383 (5)	C11—H11A	0.9700
C1—C2	1.387 (5)	C11—H11B	0.9700
C1—H1B	0.9300	C13—H13A	0.9600
C2—C3	1.371 (6)	C13—H13B	0.9600
C2—H2B	0.9300	C13—H13C	0.9600
C3—C4	1.370 (5)
C12—O3—C13	116.2 (3)	C8—C7—H7A	116.1
C10—N1—C9	127.9 (3)	C6—C7—H7A	116.1
C10—N1—H1A	120 (3)	C7—C8—C9	120.0 (3)
C9—N1—H1A	112 (3)	C7—C8—H8A	120.0
C10—N2—C11	124.3 (3)	C9—C8—H8A	120.0
C10—N2—H2A	114 (3)	O1—C9—N1	121.8 (3)
C11—N2—H2A	122 (3)	O1—C9—C8	122.9 (3)
C6—C1—C2	120.3 (3)	N1—C9—C8	115.3 (3)
C6—C1—H1B	119.8	N2—C10—N1	116.0 (3)
C2—C1—H1B	119.8	N2—C10—S1	123.9 (2)
C3—C2—C1	120.8 (4)	N1—C10—S1	120.2 (2)
C3—C2—H2B	119.6	N2—C11—C12	107.6 (3)
C1—C2—H2B	119.6	N2—C11—H11A	110.2
C4—C3—C2	119.4 (3)	C12—C11—H11A	110.2
C4—C3—H3A	120.3	N2—C11—H11B	110.2
C2—C3—H3A	120.3	C12—C11—H11B	110.2
C3—C4—C5	119.8 (3)	H11A—C11—H11B	108.5
C3—C4—H4A	120.1	O2—C12—O3	124.0 (3)
C5—C4—H4A	120.1	O2—C12—C11	125.7 (3)
C4—C5—C6	121.7 (3)	O3—C12—C11	110.3 (3)
C4—C5—H5A	119.2	O3—C13—H13A	109.5
C6—C5—H5A	119.2	O3—C13—H13B	109.5
C1—C6—C5	117.9 (3)	H13A—C13—H13B	109.5
C1—C6—C7	122.8 (3)	O3—C13—H13C	109.5
C5—C6—C7	119.2 (3)	H13A—C13—H13C	109.5
C8—C7—C6	127.8 (3)	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.88	2.610 (4)	142
N1—H1A···S1i	0.85	2.61	3.463 (4)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.88	2.610 (4)	142
N1—H1A⋯S1i	0.85	2.61	3.463 (4)	176

Symmetry code: (i) .