Blanco Maria C, Palma Alirio, Cobo Justo, Glidewell Christopher
Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
Acta Crystallogr C. 2012 Mar;68(Pt 3):o131-40. doi: 10.1107/S010827011200707X. Epub 2012 Feb 24.
The structures are reported of nine closely related tetrahydro-1,4-epoxy-1-benzazepines carrying pendant heterocyclic substituents, namely: 2-exo-(5-nitrofuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(14)H(12)N(2)O(4), (I), 7-fluoro-2-exo-(1-methyl-1H-pyrrol-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(15)FN(2)O, (II), 7-fluoro-2-exo-(5-methylfuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(14)FNO(2), (III), 7-fluoro-2-exo-(3-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(14)FNOS, (IV), 7-fluoro-2-exo-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(14)FNOS, (V), 7-chloro-2-exo-(5-methylfuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(14)ClNO(2), (VI), 2-exo-(5-methylfuran-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(16)H(14)F(3)NO(3), (VII), 2-exo-(3-methylthiophen-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(16)H(14)F(3)NO(2)S, (VIII), and 2-exo-(5-nitrofuran-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C(15)H(11)F(3)N(2)O(5), (IX). All nine compounds crystallize in centrosymmetric space groups as racemic mixtures with configuration (2RS,4SR). There are no direction-specific interactions between the molecules in (V). The molecules in (III), (IV), (VI) and (VII) are linked into simple chains, by means of a single C-H...O hydrogen bond in each of (III), (VI) and (VII), and by means of a single C-H...π(arene) hydrogen bond in (IV), while the molecules in (VIII) are linked into a chain of rings. In each of (I) and (II), a combination of one C-H...O hydrogen bond and one C-H...π(arene) hydrogen bond links the molecules into sheets, albeit of completely different construction in the two compounds. In (IX), the sheet structure is built from a combination of four independent C-H...O hydrogen bonds and one C-H...π(arene) hydrogen bond. Comparisons are made with some related compounds.
报道了9种带有侧链杂环取代基的紧密相关的四氢-1,4-环氧-1-苯并氮杂䓬的结构，即：2-外型-(5-硝基呋喃-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(14)H(12)N(2)O(4)，(I)；7-氟-2-外型-(1-甲基-1H-吡咯-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(15)FN(2)O，(II)；7-氟-2-外型-(5-甲基呋喃-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(14)FNO(2)，(III)；7-氟-2-外型-(3-甲基噻吩-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(14)FNOS，(IV)；7-氟-2-外型-(5-甲基噻吩-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(14)FNOS，(V)；7-氯-2-外型-(5-甲基呋喃-2-基)-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(14)ClNO(2)，(VI)；2-外型-(5-甲基呋喃-2-基)-7-三氟甲氧基-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(16)H(14)F(3)NO(3)，(VII)；2-外型-(3-甲基噻吩-2-基)-7-三氟甲氧基-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(16)H(14)F(3)NO(2)S，(VIII)；以及2-外型-(5-硝基呋喃-2-基)-7-三氟甲氧基-2,3,4,5-四氢-1,4-环氧-1H-1-苯并氮杂䓬，C(15)H(11)F(3)N(2)O(5)，(IX)。所有9种化合物均以中心对称空间群结晶，为构型(2RS,4SR)的外消旋混合物。(V)中分子之间不存在特定方向的相互作用。(III)、(IV)、(VI)和(VII)中的分子通过(III)、(VI)和(VII)中各自的一个C-H...O氢键以及(IV)中的一个C-H...π(芳烃)氢键连接成简单链，而(VIII)中的分子连接成环链。在(I)和(II)中，一个C-H...O氢键和一个C-H...π(芳烃)氢键的组合将分子连接成片，尽管这两种化合物中的片层结构完全不同。在(IX)中，片层结构由四个独立的C-H...O氢键和一个C-H...π(芳烃)氢键组合而成。并与一些相关化合物进行了比较。
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