Ethyl 4-anilino-2,6-bis-(4-fluoro-phen-yl)-1-phenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Acta Crystallogr Sect E Struct Rep Online

Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India.

Published: February 2013

In the title compound, C(32)H(28)F(2)N(2)O(2), the tetra-hydro-pyridine ring adopts a distorted boat conformation. The two fluoro-phenyl groups are attached to the tetra-hydro-pyridine ring in a trans orientation. The dihedral angle between the planes of the fluoro-substituted rings is 57.0 (1)°. The amino group and carbonyl O atom are involved in intra-molecular hydrogen bonding. In the crystal, weak C-H⋯O, C-H⋯F and C-H⋯π inter-actions link the mol-ecules into columns along [010].

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569819PMC
http://dx.doi.org/10.1107/S1600536813002158DOI Listing

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Article Synopsis
  • - The compound CHFNO, a tetrahydropyridine, is synthesized through a one-pot reaction using 4-fluoro-aniline, ethyl acetoacetate, and benzaldehyde at room temperature, utilizing sodium lauryl sulfate as a catalyst.
  • - In its crystal form, CHFNO contains two molecules in the asymmetric unit and features a distorted boat conformation, with hydrogen bonding interactions contributing to its three-dimensional structure.
  • - Computational analysis using density functional theory (DFT) compares the optimized molecular structure with experimental data and examines the compound’s electronic properties through HOMO-LUMO behavior and Natural Bond Orbital (NBO) analysis.
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In 2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile hemihydrate, CHBrNO·0.5HO, (I), pairs of mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming dimers with an (12) ring motif. The dimers are connected by N-H⋯Br and O-H⋯O hydrogen bonds, and C-Br⋯π inter-actions, forming layers parallel to the (010) plane.

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Crystal structure and Hirshfeld surface analysis of 5-acetyl-2-amino-4-(4-bromo-phen-yl)-6-oxo-1-phenyl-1,4,5,6-tetra-hydro-pyridine-3-carbo-nitrile.

Acta Crystallogr E Crystallogr Commun

February 2022

Acad. Sci. Republ. Tajikistan, Kh. Yu. Yusufbekov Pamir Biol. Inst., 1 Kholdorova str., 736002, Khorog, Gbao, Tajikistan.

The crystal structure of the title compound, CHBrNO, was determined using an inversion twin. Its asymmetric unit comprises two crystallographically independent mol-ecules ( and ) being the stereoisomers. Both mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming a dimer with an (16) ring motif.

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The central tetra-hydro-pyridine ring of the title compound, CHNO, adopts a screw-boat conformation. In the crystal, strong C-H⋯O and N-H⋯N hydrogen bonds form dimers with (14) and (12) ring motifs, respectively, between consecutive mol-ecules along the -axis direction. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds connect these dimers, forming a three-dimensional network.

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The mol-ecular conformation of the title compound, CHClNO, is stabilized by an intra-molecular O-H⋯O hydrogen bond, forming an (6) ring motif. The central pyridine ring is almost planar [maximum deviation = 0.074 (3) Å].

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