Vimala G, Poomathi N, Perumal P T, SubbiahPandi A
Department of Physics, Presidency College (Autonomous), Chennai 600 005, India.
Organic Chemistry, CSIR - Central Leather Research Institute, Adyar, Chennai 600 020, India.
Acta Crystallogr E Crystallogr Commun. 2016 Jan 30;72(Pt 2):261-5. doi: 10.1107/S2056989016001493. eCollection 2016 Feb 1.
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.
标题化合物C₁₉H₁₆ClNO₅(I)和C₁₉H₁₅Cl₂NO₅(II)均结晶于单斜空间群P2₁/n。它们的主要区别在于乙酸甲酯基团的取向,在(I)中C=O键指向NO₂基团,而在(II)中则远离该基团。在化合物(I)中,丙烯酸甲酯单元的平均平面是平的,甲基C原子的最大偏差为0.0044(2)Å,而在(II)中该偏差为0.0147 Å。对于化合物(I)和(II),两个芳香环之间的面间角分别为74.87(9)°和75.65(2)°。在这两种化合物中,丙烯酸甲酯和硝基乙烯基围绕C=C键均采取E构象。在(I)的晶体中,分子通过C-H⋯O氢键相连,沿b轴形成链。这些链通过C-H⋯Cl氢键相连,形成平行于ab平面的片层。这些片层通过C-H⋯π相互作用相连,形成三维结构。在(II)的晶体中,分子通过成对的C-H⋯O氢键相连,形成具有R₂²(30)环 motif的反演二聚体。这些二聚体通过C-H⋯O氢键相连,形成平行于ac平面并包含R₄⁴(28)环motif的片层。这些片层通过平行滑移的π-π相互作用(质心间距均约为3.86 Å)相连,形成三维结构。