Home Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S
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Crystal structure of (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate, C14H14N2O2S

  • Yahia N. Mabkhot EMAIL logo , Hazem A. Ghabbour , Faiz A. Al-aizari and Salim Al-Showiman
Published/Copyright: October 10, 2016

Abstract

C14H14N2O2S, triclinic, P1̄, a = 8.6471(4) Å, b = 9.5576(5) Å, c = 9.7098(5) Å, α = 91.054(2)°, β = 109.380(2)°, γ = 113.769(2)°, V = 681.95(6) Å3, Z = 2, Rgt(F) = 0.061, wRref(F2) = 0.175, T = 296(2).

CCDC no.:: 1484500

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless block Size 0.32 × 0.26 × 0.24 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.4 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:19934, 3119, 0.049
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2345
N(param)refined:173
Programs:Bruker programs [12], SHELX [13]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
S10.57896(10)0.36123(8)0.14783(8)0.0524(3)
O10.2177(3)0.2648(3)0.0047(3)0.0708(7)
O20.0428(3)0.3411(3)0.0835(3)0.0779(8)
N10.6838(3)0.6103(2)0.3276(2)0.0391(5)
N20.2674(4)0.6137(3)0.3722(3)0.0662(8)
C10.7642(5)0.7946(4)0.5420(3)0.0672(9)
H1A0.80390.73050.60410.081*
C20.7753(7)0.9313(5)0.6024(5)0.0902(13)
H2A0.82240.96110.70710.108*
C30.7203(5)1.0241(4)0.5149(5)0.0750(11)
H3A0.72591.11690.55820.090*
C40.6564(5)0.9837(4)0.3639(5)0.0703(9)
H4A0.61961.04960.30260.084*
C50.6449(4)0.8474(3)0.3000(3)0.0541(7)
H5A0.60320.82040.19520.065*
C60.6945(3)0.7523(3)0.3900(3)0.0387(5)
C70.8553(4)0.6050(4)0.3404(4)0.0622(8)
H7A0.92010.68520.29090.075*
H7B0.93460.62570.44620.075*
C80.8136(5)0.4511(5)0.2705(5)0.0839(12)
H8A0.83570.38720.34720.101*
H8B0.89280.46000.21410.101*
C90.5325(3)0.4940(3)0.2338(3)0.0344(5)
C100.3550(3)0.4713(3)0.2064(3)0.0381(5)
C110.2045(4)0.3489(3)0.0895(3)0.0503(7)
C12−0.1216(5)0.2288(6)−0.0327(4)0.0952(14)
H12A−0.20470.2772−0.07530.114*
H12B−0.09040.1956−0.11290.114*
C13−0.2075(8)0.1007(5)0.0242(6)0.1189(19)
H13A−0.32900.0353−0.04930.178*
H13B−0.21840.13540.11470.178*
H13C−0.13590.04080.04750.178*
C140.3118(3)0.5551(3)0.2986(3)0.0441(6)

Source of material

The synthesis of (Z)-ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate proceeded by a reaction of ethylcyanoacetate (1 mmol) in 10 mL DMF/C2H5OH and phenylisothiocyanate (1 mmol) at presence of K2CO3. The reaction mixture was stirred for 10 h. The residue was recrystallized from DMF/C2H5OH. (Z)-Ethyl 2-cyano-2-(3-phenylthiazolidin-2-ylidene) acetate (C14H14N2O2S), yellow crystals; yield (35%); m.p.: 205 °C; 1H-NMR (400 MHz, CDCl3): δ 1.84 (s, CH3), 3.19 (t, CH2), 3.27 (t, CH2), 4.31 (q, CH2) 7.56–7.50 (m, Ar) ppm; 13C-NMR (400 MHz, CDCl3): δ 14.28, 17.85, 26.24, 29.57, 60.25, 94.90, 118.47, 123.57, 140.91, 155.42, 158.92, 147.3, 163.91, 198.31 ppm.

Experimental details

C-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation. The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density.

Discussion

This contribution is part of our continuing interest in the syntheses and crystal structures of small organic compounds [1], [2], [3], [4]. Thiazole compounds are an important in heterocyclic [5], [6], [7], [8], and also used in coordination chemistry [9] and are known as powerful inhibitors of carbonic anhydrase activity [8], [9], [10], [11].

The asymmetric unit cell of the title compound contains one molecule. The bond length of C9—C10 is 1.390(3) Å which is a typical C = C double bond and the configuration around this double bond is Z. The molecules are packed in the crystal structure at least by one non-classical intermolecular hydrogen bond C3—H3A⋯N2i. The H⋯A distance is 2.62 Å and the angle is 169°. Symmetry codes: (i) − x + 1, − y + 2, − z + 1.

Acknowledgements

The authors extend their sincere appreciation to the Deanship of Scientific Research at king Saud University for its funding this Prolific Research group (PRG-1437-29).

References

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Received: 2016-6-19
Accepted: 2016-9-14
Published Online: 2016-10-10
Published in Print: 2017-1-1

©2016 Yahia N. Mabkhot et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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