2-Eth­oxy­ethyl (Z)-2-cyano-3-[(N-phenyl­carbamo­yl)amino]­prop-2-enoate

Shihua Zhong; Dongmei Wei; Jianbing Liu; Bingyu Liu

doi:10.1107/S1600536811055000

. 2012 Jan 7;68(Pt 2):o267. doi: 10.1107/S1600536811055000

2-Ethoxyethyl (Z)-2-cyano-3-[(N-phenylcarbamoyl)amino]prop-2-enoate

Shihua Zhong ^a, Dongmei Wei ^a, Jianbing Liu ^a,^*, Bingyu Liu ^a

PMCID: PMC3274966 PMID: 22346911

Abstract

The crystal structure of the title compound, C₁₅H₁₇N₃O₄, is stabilized by intermolecular N—H⋯N hydrogen bonds. An intramolecular N—H⋯O hydrogen bond also occurs.

Related literature

The title compound was synthesized as a possible novel herbicide. For details of the synthesis, see: Wang et al. (2004 ▶); Senda et al. (1972 ▶). For reviews of cyanoacrylate derivatives as bioactive agents, see: Zhang et al. (2008 ▶); Liu et al. (1998 ▶).

Experimental

Crystal data

C₁₅H₁₇N₃O₄
M _r = 303.32
Monoclinic,
a = 25.102 (7) Å
b = 12.013 (3) Å
c = 10.436 (3) Å
β = 96.248 (4)°
V = 3128.4 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 153 K
0.48 × 0.44 × 0.09 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.956, T _max = 0.992
16240 measured reflections
4149 independent reflections
2994 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.116
S = 1.00
4149 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055000/hg5148sup1.cif

e-68-0o267-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055000/hg5148Isup2.hkl

e-68-0o267-Isup2.hkl^{(203.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055000/hg5148Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.910 (15)	2.068 (15)	2.7543 (14)	131.2 (12)
N1—H1N⋯N3ⁱ	0.867 (15)	2.050 (15)	2.9120 (15)	172.6 (14)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to Hunan Normal University for financial support and thank Mr Kai-bei Yu of Beijing Institute of Technology for the X-ray crystallographic data collection and structure determination.

supplementary crystallographic information

Comment

Previous studies have shown that cyanoacrylate derivatives are an important class of compounds with high bioactivities and can be applied as herbicide (Zhang et al., 2008), urea derivatives also exhibit good herbicidal activities (Liu et al., 1998), both kinds of compounds are inhibitors of photosystem II electron transport and inhibit the growth of weeds by disrupting photosynthetic electron transport. A novel cyanoacrylate compound (C₁₅H₁₇N₃O₄) which bears a phenyl urea unit was synthesized and investigated for its ability to inhibit PSII electron transport, its crystal structure is reported here.

The crystal structure of title compound is stabilized by inter-molecular N—H···N hydrogen bonds, the orientation of phenylurea and ester carbonyl is cis and an intramolecular N—H···O hydrogen bond was generated to stabilize the conformation.

Experimental

The title compound was prepared according to the reported method (Wang et al., 2004; Senda et al., 1972). A mixture of 2-ethoxyethyl cyanoacetate (0.55 g, 3.5 mmol), Phenylurea (0.39 g 2.9 mmol) and triethyl orthoformate (0.59 ml, 3.5 mmol) was heated at 378 K for 2 hr, cooled to room temperature, the precipitation was filtered off, washed with hexane and recrystallized from ethanol to give white solid (yield 37%), mp: 458 K. Crystals of (I) suitable for XRD were obtained by slow evaporation of a mixture solution of ethanol and acetone in a ratio of 1:2 at 293 K.