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Crystal structures of methyl (E)-3-(2-chloro­phen­yl)-2-({2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)acrylate and methyl (E)-2-({4-chloro-2-[(E)-2-nitro­vin­yl]phen­oxy}meth­yl)-3-(2-chloro­phen­yl)acrylate

The title compounds, C(19)H(16)ClNO(5), (I), and C(19)H(15)Cl(2)NO(5), (II), both crystallize in the monoclinic space group P2(1)/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO(2) group in (I) but away from it in (II). In compound...

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Detalles Bibliográficos
Autores principales: Vimala, G., Poomathi, N., Perumal, P. T., SubbiahPandi, A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4770962/
https://www.ncbi.nlm.nih.gov/pubmed/26958402
http://dx.doi.org/10.1107/S2056989016001493
Descripción
Sumario:The title compounds, C(19)H(16)ClNO(5), (I), and C(19)H(15)Cl(2)NO(5), (II), both crystallize in the monoclinic space group P2(1)/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO(2) group in (I) but away from it in (II). In compound (I), the mean plane of the methyl acrylate unit is planar, with a maximum deviation of 0.0044 (2) Å for the methyl C atom, while in (II) this deviation is 0.0147 Å. The inter­planar angles between the two aromatic rings are 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In both compounds, the methyl acrylate and nitro­vinyl groups each adopt an E conformation about the C=C bond. In the crystal of (I), mol­ecules are linked by C—H⋯O hydrogen bonds forming chains along the b axis. The chains are linked via C—H⋯Cl hydrogen bonds, forming sheets parallel to the ab plane. The sheets are linked via C—H⋯π inter­actions, forming a three-dimensional structure. In the crystal of (II), mol­ecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R (2) (2)(30) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane and enclosing R (4) (4)(28) ring motifs. The sheets are linked via parallel slipped π–π inter­actions (inter­centroid distances are both ca 3.86 Å), forming a three-dimensional structure.