Abstract
The title compounds, C19H16ClNO5, (I), and C19H15Cl2NO5, (II), both crystallize in the monoclinic space group P21/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO2 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 inter-planar 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 nitro-vinyl groups each adopt an E conformation about the C=C bond. In the crystal of (I), mol-ecules 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 inter-actions, forming a three-dimensional structure. In the crystal of (II), mol-ecules 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 inter-actions (inter-centroid distances are both ca 3.86 Å), forming a three-dimensional structure.
Highlights
C atom, while in (II) this deviation is 0.0147 Å
In the crystal of (I), molecules are linked by C—H O hydrogen bonds forming chains along the b axis
In the crystal of (II), molecules are linked by pairs of C—
Summary
2-cyanoacrylates have been used extensively as agrochemicals because of their unique mechanism of action and good environmental profiles (Govindan et al, 2011). Cinnamic acid derivatives have received attention in medicinal research as traditional as well as recently synthetic antitumor agents (De et al, 2011). They possess significant antibacterial activity against Staphylococcus aureus (Xiao et al, 2008). Different substitutions on the basic moiety lead to various pharmacological activities, such as anti-oxidant, hepatoprotective, anxiolytic, insect repellent, antidiabetic and anticholesterolemic (Sharma, 2011). Against this background, the title compounds were synthesized and we report on their crystal structures
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More From: Acta crystallographica. Section E, Crystallographic communications
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