Xianghan Zhang, Lanying Wang, Y. Zhan
May 17, 2011
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Influential Citations
20
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract A merocyanine dye with isoxazolone nucleus: 4-[(5-methoxy-1H-indole-3-yl)-methylene]-3-methyl-isoxazole-5-one ( 1 ) was synthesized and characterized by X-ray diffraction, 1 H NMR, 13 C NMR, IR, UV–Vis spectra and elemental analysis. The crystals are monoclinic, space group P 2 1 /n, with a = 6.4195(16), b = 7.5759(19), c = 25.181(6) A, V = 1217.9(5) A 3 , and Z = 4 (at 298(2) K). Crystal stacking scheme indicates the hydrogen bonds and intermolecular face-to-face π⋯π aromatic stacking interactions generate a unique parallelogram-void supramolecular architecture in solid state of the dye ( 1 ). By DFT calculations, molecular electrostatic potential clearly shows that the formation of hydrogen-bonding interaction [N(2) H(2)⋯O(2) and C(1) H(1A)⋯N(1)] in the crystal structure is between the positive and negative regions. In addition, molecular geometry, tautomeric forms, 1 H NMR and 13 C NMR were calculated by DFT/GIAO (the gauge invariant atomic orbital) methods are in good agreement with the experimental values. The correlation value between experimental 13 C chemical shifts and the calculated magnetic isotropic shielding tensors is 0.9989, and the absolute deviation is 0.2–4.4 based on B3LYP/6-31G * -PCM (the polarizable continuum model) level.