Tewes Bastian, Frehland Bastian, Fröhlich Roland, Wünsch Bernhard
Institut für Pharmazeutische und Medizinische Chemie der Universität Münster, Corrensstrasse 48, D-48149 Münster, Germany.
Organisch-chemisches Institut der Westfälischen Wilhelms-Universität Münster, Corrensstr. 40, D-48149-Münster, Germany.
Acta Crystallogr E Crystallogr Commun. 2016 Apr 15;72(Pt 5):687-91. doi: 10.1107/S2056989016005843. eCollection 2016 May 1.
The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is -anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenyl-butyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, mol-ecules are linked via O-H⋯N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane.
标题化合物C22H29NO2（3）和C22H29NO2（4）[系统名称：(1S*,2R*)-7-甲氧基-2-甲基-3-(4-苯基丁基)-2,3,4,5-四氢-1H-3-苯并氮杂卓-1-醇和(1R*,2R*)-7-甲氧基-2-甲基-3-(4-苯基丁基)-2,3,4,5-四氢-1H-3-苯并氮杂卓-1-醇]是非对映异构体，七元氮杂卓环上相邻羟基和甲基的相对构型在（3）中为反式，在（4）中为顺式。在晶体中，这些基团的取向为-反叠式（3）和+顺错式（4）。在这两种情况下，所研究的晶体均为外消旋混合物，相对构型为(R*,S*)-3和(R*,R*)-4。在这两种化合物中，七元氮杂卓环均呈椅式构象，(R*,S*)-3中的4-苯基丁基侧链呈伸展构象，而(R*,R*)-4中的则呈扭曲构象。在(S*,R*)-3的晶体中，分子通过C-H⋯O氢键相连，形成平行于ac平面的片层。在(R*,R*)-4的晶体中，分子通过O-H⋯N氢键相连，形成沿c轴方向延伸的链。这些链通过C-H⋯O氢键相连，形成平行于ac平面的片层。
