Investigation of three diasteromeric chalcone epoxides derivatives by nmr spectroscopy and X-ray crystallography
Por:
Obregón-Mendoza M.A., Escobedo-Martínez C., Lozada M.C., Gnecco D., Soriano-García M., Enríquez R.G.
Publicada:
1 oct 2014
Resumen:
Structures of diasteromeric chalcone epoxides derivatives [3-(4-nitrophenyl)oxiran-2-yl)(phenyl)]-methanone (C15H11NO4), compound 1; (3,4-dimethoxy phenyl)-(3-(4-nitrophenyl)-oxiran-2-yl)methanone (C17H15NO6) compound 2 and [(3-(4-nitrophenyl)-oxiran-2-yl) phenyl-methanol] (C15H13NO4) compound 3 were established by spectral and X-ray diffraction studies. Compound 1 crystallizes in the monoclinic space group P21/c with unit cell parameters a = 10.3127(10), b = 10.45331(10), c = 12.9227(13) Å, ß = 113.769(2)°, Z = 4. Compound 2 crystallizes in the triclinic space group P-1 with unit cell parameters a = 6.977(1), b = 8.259(1), c = 13.964(2) Å, a = 103.889(2), ß = 91.151(2), ? = 100.780(2)°, Z = 2. Compound 3 crystallizes in the monoclinic space group P21 with unit cell parameters a = 6.708(1), b = 8.388(1), c = 12.407(2) Å, ß = 103.322(3)°, Z = 2. The absolute configurations of 3 for the chiral centers are 1S, 2R, and 3R. In structures 1 and 2, the molecules in the crystal are linked by C-H···O interactions and van der Waals forces. Molecules 2 in the crystal are stacked in an anti-parallel fashion along the a-axis by p···p interactions which gives additional support to molecular packing stability. In structure 3, the molecules in the crystal are linked by both intra- and intermolecular hydrogen bonds O1-H···O2 and O1-H···O4, respectively. Adjacent molecules are interconnected by intermolecular weak C-H···O interactions. Graphical Abstract: Structures of three diasteromeric chalcone epoxides derivatives [3-(4-nitrophenyl)oxiran-2-yl)(phenyl)]-methanone 1; (3,4-dimethoxyphenyl)-(3-(4-nitrophenyl)-oxiran-2-yl)methanone 2 and [(3-(4-nitro phenyl)-oxiran-2-yl) phenyl-methanol] 3 were established by spectral and X-ray diffraction studies. The geometric parameters of the oxirane ring are in good agreement with those found in the literature and exist as trans isomer. The crystal packing in all three structures is stabilized by weak intermolecular C-H···O interactions. In structure 3, the molecules in the crystal are internally stabilized by both intra- and intermolecular O-H···O hydrogen bonds.[Figure not available: see fulltext.] © 2014 Springer Science+Business Media New York.
Filiaciones:
Obregón-Mendoza M.A.:
Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
Escobedo-Martínez C.:
División de Ciencias Naturales y Exactas Del Campus Guanajuato, Departamento de Farmacia, Universidad de Guanajuato, Col. Noria Alta s/n., C.P Guanajuato Gto, 36050, Mexico
Lozada M.C.:
Departamento de Sistemas Biológicos, UAM-Xochimilco, Calzada del Hueso 1100 Col. Villa Quietud, Coyoacán, Mexico, 04960, Mexico
Gnecco D.:
Centro de Química, BUAP Puebla, Mexico, Mexico
Soriano-García M.:
Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
Enríquez R.G.:
Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
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