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

In the title compound, C(14)H(16)N(2)O(3)S, the phenyl ring and the ethyl 2-(3-formyl-thio-ureido)acetate fragment adopt an E configuration with respect to the C=C bond. An intra-molecular N-H⋯O hydrogen bond generating an S(6) ring motif is observed. In the crystal, mol-ecules are linked by N-H⋯S, C-H⋯S and C-H⋯O hydrogen bonds, forming sheets lying parallel to the ab plane.

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 synthesis, see: Hassan et al. (2008a ▶).

Experimental

Crystal data

C14H16N2O3S

M = 292.35

Orthorhombic,

a = 5.1867 (9) Å

b = 9.7417 (16) Å

c = 29.154 (5) Å

V = 1473.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.49 × 0.38 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.897, T max = 0.947

10938 measured reflections

3637 independent reflections

2747 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.164

S = 1.03

3637 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1497 Friedel pairs

Flack parameter: −0.04 (13)

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/S1600536810037918/ci5178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037918/ci5178Isup2.hkl

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

C14H16N2O3S	F(000) = 616
Mr = 292.35	Dx = 1.318 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2524 reflections
a = 5.1867 (9) Å	θ = 2.2–25.5°
b = 9.7417 (16) Å	µ = 0.23 mm−1
c = 29.154 (5) Å	T = 298 K
V = 1473.1 (4) Å3	Block, colourless
Z = 4	0.49 × 0.38 × 0.24 mm

Bruker SMART APEX CCD area-detector diffractometer	3637 independent reflections
Radiation source: fine-focus sealed tube	2747 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scan	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −6→6
Tmin = 0.897, Tmax = 0.947	k = −12→13
10938 measured reflections	l = −32→38

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.036
3637 reflections	Δρmax = 0.35 e Å−3
182 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 1497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (13)

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	−0.18635 (18)	0.08578 (8)	0.03548 (2)	0.0573 (2)
O1	0.3380 (5)	0.2635 (3)	0.14456 (7)	0.0694 (7)
O2	0.0044 (6)	−0.0041 (3)	0.20692 (9)	0.0952 (10)
O3	−0.3348 (5)	−0.1415 (2)	0.19707 (7)	0.0712 (7)
N1	0.1857 (5)	0.2377 (2)	0.07184 (7)	0.0446 (5)
H1A	0.2047	0.2655	0.0440	0.053*
N2	−0.0312 (5)	0.0950 (2)	0.12136 (8)	0.0494 (6)
H2A	0.0690	0.1285	0.1420	0.059*
C1	0.9341 (6)	0.5968 (3)	0.05420 (11)	0.0540 (7)
H1B	0.8379	0.5558	0.0310	0.065*
C2	1.1166 (7)	0.6944 (3)	0.04298 (12)	0.0630 (9)
H2B	1.1426	0.7182	0.0124	0.076*
C3	1.2592 (6)	0.7563 (3)	0.07652 (12)	0.0635 (9)
H3A	1.3788	0.8236	0.0689	0.076*
C4	1.2251 (7)	0.7186 (3)	0.12129 (13)	0.0661 (9)
H4A	1.3249	0.7593	0.1441	0.079*
C5	1.0440 (7)	0.6208 (3)	0.13305 (11)	0.0581 (8)
H5A	1.0234	0.5962	0.1637	0.070*
C6	0.8916 (5)	0.5586 (3)	0.09962 (10)	0.0450 (6)
C7	0.7010 (6)	0.4568 (3)	0.11298 (10)	0.0487 (6)
H7A	0.6949	0.4335	0.1439	0.058*
C8	0.5352 (6)	0.3939 (3)	0.08554 (10)	0.0451 (6)
H8A	0.5372	0.4125	0.0543	0.054*
C9	0.3480 (6)	0.2950 (3)	0.10411 (9)	0.0465 (6)
C10	−0.0050 (6)	0.1404 (3)	0.07938 (10)	0.0439 (6)
C11	−0.2162 (6)	−0.0072 (3)	0.13555 (10)	0.0514 (7)
H11A	−0.2033	−0.0869	0.1158	0.062*
H11B	−0.3892	0.0297	0.1328	0.062*
C12	−0.1669 (7)	−0.0482 (3)	0.18390 (11)	0.0604 (8)
C13	−0.3116 (12)	−0.1938 (5)	0.24386 (13)	0.1039 (16)
H13A	−0.1398	−0.2299	0.2490	0.125*
H13B	−0.3433	−0.1210	0.2658	0.125*
C14	−0.5011 (16)	−0.3012 (7)	0.24893 (19)	0.165 (3)
H14A	−0.4645	−0.3534	0.2761	0.247*
H14B	−0.4953	−0.3606	0.2227	0.247*
H14C	−0.6697	−0.2612	0.2514	0.247*

	U11	U22	U33	U12	U13	U23
S1	0.0656 (5)	0.0633 (4)	0.0430 (4)	−0.0139 (4)	−0.0054 (4)	−0.0001 (3)
O1	0.0813 (16)	0.0836 (14)	0.0431 (11)	−0.0360 (15)	−0.0067 (11)	0.0109 (10)
O2	0.105 (2)	0.113 (2)	0.0677 (17)	−0.049 (2)	−0.0235 (16)	0.0243 (17)
O3	0.0789 (16)	0.0854 (15)	0.0494 (12)	−0.0338 (14)	−0.0044 (12)	0.0145 (11)
N1	0.0475 (12)	0.0476 (11)	0.0386 (11)	−0.0068 (12)	0.0019 (11)	0.0020 (9)
N2	0.0518 (14)	0.0541 (13)	0.0422 (12)	−0.0123 (12)	−0.0024 (10)	0.0020 (11)
C1	0.0510 (17)	0.0602 (16)	0.0509 (16)	−0.0087 (15)	−0.0081 (13)	0.0023 (14)
C2	0.063 (2)	0.0684 (18)	0.0579 (19)	−0.0092 (17)	0.0024 (15)	0.0120 (15)
C3	0.053 (2)	0.0544 (16)	0.084 (2)	−0.0068 (15)	0.0053 (16)	−0.0015 (16)
C4	0.059 (2)	0.0655 (19)	0.073 (2)	−0.0121 (16)	−0.0086 (17)	−0.0198 (17)
C5	0.0598 (19)	0.0647 (19)	0.0497 (17)	−0.0059 (17)	−0.0031 (14)	−0.0092 (14)
C6	0.0396 (14)	0.0439 (14)	0.0513 (15)	0.0033 (11)	−0.0010 (12)	−0.0043 (11)
C7	0.0519 (16)	0.0515 (14)	0.0427 (14)	0.0005 (14)	0.0013 (13)	0.0001 (11)
C8	0.0464 (15)	0.0455 (14)	0.0433 (14)	−0.0002 (13)	−0.0003 (12)	0.0017 (11)
C9	0.0473 (16)	0.0472 (14)	0.0449 (14)	−0.0019 (13)	−0.0044 (12)	0.0012 (11)
C10	0.0431 (16)	0.0393 (12)	0.0492 (15)	0.0014 (12)	−0.0004 (12)	−0.0028 (11)
C11	0.0502 (16)	0.0538 (15)	0.0503 (15)	−0.0080 (14)	−0.0016 (13)	0.0065 (12)
C12	0.0631 (19)	0.0642 (18)	0.0538 (17)	−0.0143 (18)	0.0004 (17)	0.0043 (13)
C13	0.124 (4)	0.125 (3)	0.062 (2)	−0.041 (4)	−0.012 (3)	0.038 (2)
C14	0.184 (6)	0.229 (8)	0.083 (3)	−0.108 (6)	−0.038 (4)	0.083 (4)

S1—C10	1.675 (3)	C4—C5	1.381 (5)
O1—C9	1.219 (3)	C4—H4A	0.93
O2—C12	1.193 (4)	C5—C6	1.393 (4)
O3—C12	1.316 (4)	C5—H5A	0.93
O3—C13	1.462 (4)	C6—C7	1.453 (4)
N1—C9	1.380 (4)	C7—C8	1.325 (4)
N1—C10	1.387 (4)	C7—H7A	0.93
N1—H1A	0.86	C8—C9	1.472 (4)
N2—C10	1.308 (4)	C8—H8A	0.93
N2—C11	1.443 (4)	C11—C12	1.487 (4)
N2—H2A	0.86	C11—H11A	0.97
C1—C2	1.381 (4)	C11—H11B	0.97
C1—C6	1.393 (4)	C13—C14	1.443 (7)
C1—H1B	0.93	C13—H13A	0.97
C2—C3	1.366 (5)	C13—H13B	0.97
C2—H2B	0.93	C14—H14A	0.96
C3—C4	1.367 (5)	C14—H14B	0.96
C3—H3A	0.93	C14—H14C	0.96
C12—O3—C13	117.3 (3)	C7—C8—H8A	119.7
C9—N1—C10	127.1 (2)	C9—C8—H8A	119.7
C9—N1—H1A	116.5	O1—C9—N1	122.2 (3)
C10—N1—H1A	116.5	O1—C9—C8	123.2 (3)
C10—N2—C11	124.8 (2)	N1—C9—C8	114.6 (2)
C10—N2—H2A	117.6	N2—C10—N1	117.0 (2)
C11—N2—H2A	117.6	N2—C10—S1	123.3 (2)
C2—C1—C6	121.2 (3)	N1—C10—S1	119.7 (2)
C2—C1—H1B	119.4	N2—C11—C12	110.0 (3)
C6—C1—H1B	119.4	N2—C11—H11A	109.6
C3—C2—C1	120.3 (3)	C12—C11—H11A	109.6
C3—C2—H2B	119.8	N2—C11—H11B	109.7
C1—C2—H2B	119.8	C12—C11—H11B	109.7
C2—C3—C4	119.7 (3)	H11A—C11—H11B	108.2
C2—C3—H3A	120.2	O2—C12—O3	125.3 (3)
C4—C3—H3A	120.2	O2—C12—C11	124.3 (3)
C3—C4—C5	120.6 (3)	O3—C12—C11	110.4 (3)
C3—C4—H4A	119.7	C14—C13—O3	107.0 (4)
C5—C4—H4A	119.7	C14—C13—H13A	110.3
C4—C5—C6	120.8 (3)	O3—C13—H13A	110.3
C4—C5—H5A	119.6	C14—C13—H13B	110.3
C6—C5—H5A	119.6	O3—C13—H13B	110.3
C5—C6—C1	117.3 (3)	H13A—C13—H13B	108.6
C5—C6—C7	119.7 (3)	C13—C14—H14A	109.5
C1—C6—C7	123.0 (3)	C13—C14—H14B	109.5
C8—C7—C6	126.5 (3)	H14A—C14—H14B	109.5
C8—C7—H7A	116.7	C13—C14—H14C	109.5
C6—C7—H7A	116.7	H14A—C14—H14C	109.5
C7—C8—C9	120.6 (3)	H14B—C14—H14C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1i	0.86	2.79	3.631 (2)	166
N2—H2A···O1	0.86	1.92	2.611 (4)	137
C4—H4A···O3ii	0.93	2.54	3.457 (4)	170
C8—H8A···S1i	0.93	2.86	3.716 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1i	0.86	2.79	3.631 (2)	166
N2—H2A⋯O1	0.86	1.92	2.611 (4)	137
C4—H4A⋯O3ii	0.93	2.54	3.457 (4)	170
C8—H8A⋯S1i	0.93	2.86	3.716 (3)	153

Symmetry codes: (i) ; (ii) .