Palma Alirio, Bahsas Ali, Yépes Andrés F, Cobo Justo, Hursthouse Michael B, Glidewell Christopher
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
Acta Crystallogr C. 2009 Apr;65(Pt 4):o140-5. doi: 10.1107/S0108270109005265. Epub 2009 Mar 7.
(2R,4S)-7-Bromo-2-phenyl-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C(20)H(16)BrNO, (I), exhibits evidence of a modest degree (ca 10%) of inversion twinning, while both (2RS,4SR)-7-bromo-2-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C(20)H(15)BrClNO, (II), and (2RS,4SR)-2-(4-fluorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C(20)H(16)FNO, (III), crystallize as genuine racemic mixtures. The molecules of (I) are linked into sheets by a combination of one C-H...O hydrogen bond and two C-H...pi(arene) hydrogen bonds, while those of (II) are linked into sheets of pi-stacked hydrogen-bonded chains. A combination of one C-H...O hydrogen bond and four independent C-H...pi(arene) hydrogen bonds links the molecules of (III) into a three-dimensional framework. The significance of this study lies in its finding, via comparison with the structures of some closely-related epoxybenzazepine analogues, of significant changes in crystal structures consequent upon small changes in the peripheral substituents.
(2R,4S)-7-溴-2-苯基-2,3,4,5-四氢-1,4-环氧萘并[1,2-b]氮杂卓，C(20)H(16)BrNO，(I)，表现出适度程度（约10%）的倒转孪晶迹象，而(2RS,4SR)-7-溴-2-(4-氯苯基)-2,3,4,5-四氢-1,4-环氧萘并[1,2-b]氮杂卓，C(20)H(15)BrClNO，(II)，以及(2RS,4SR)-2-(4-氟苯基)-2,3,4,5-四氢-1,4-环氧萘并[1,2-b]氮杂卓，C(20)H(16)FNO，(III)，均以真正的外消旋混合物形式结晶。(I)的分子通过一个C-H...O氢键和两个C-H...π(芳烃)氢键的组合连接成片，而(II)的分子连接成π堆积氢键链的片层。一个C-H...O氢键和四个独立的C-H...π(芳烃)氢键的组合将(III)的分子连接成三维框架。这项研究的意义在于，通过与一些密切相关的环氧苯并氮杂卓类似物的结构进行比较，发现外围取代基的微小变化会导致晶体结构发生显著变化。
