Chain formation by disordered, but correlated, hydrogen bonds in cis-(2RS,4SR)-2-(thio­phen-2-yl)-2,3,4,5-tetra­hydro-1H-1-benzazepin-4-ol and cis-(2RS,4SR)-2-(5-methyl­thio­phen-2-yl)-2,3,4,5-tetra­hydro-1H-1-benz­azepin-4-ol

The closely related compounds cis-(2RS,4SR)-2-(thio­phen-2-yl)-2,3,4,5-tetra­hydro-1H-1-benzazepin-4-ol, C₁₄H₁₅NOS, (I), and cis-(2RS,4SR)-2-(5-methyl­thio­phen-2-yl)-2,3,4,5-tetra­hy­dro-1H-1-benzazepin-4-ol, C₁₅H₁₇NOS, (II), both crystallize with Z' = 2 in the space group P. In (I), the thienyl substituent in one of the two independent mol­ecules is disordered over two sets of atomic sites having occupancies of 0.856 (2) and 0.144 (2). In both compounds, the two independent hy­droxy O atoms are both within 2.8 Å of the hy­droxy O atoms of two neighbouring mol­ecules, and all of the hy­droxy H atoms are disordered, each over two sites. The resulting O-H...O hydrogen bonds generate two similar but distinct C₄⁴(8) chains, depending upon which hy­droxy H-atom sites are occupied or vacant, with full correlation of the hy­droxy H-atom occupancies within each chain. Comparisons are made with the supra­molecular assembly in some related compounds.

Nine closely related tetra­hydro-1,4-ep­oxy-1-benzazepines carrying pendant heterocyclic substituents: hydrogen-bonded supra­molecular assembly in zero, one and two dimensions

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, C₁₄H₁₂N₂O₄, (I), 7-fluoro-2-exo-(1-methyl-1H-pyrrol-2-yl)-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₅FN₂O, (II), 7-fluoro-2-exo-(5-methyl­furan-2-yl)-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₄FNO₂, (III), 7-fluoro-2-exo-(3-methylthio­phen-2-yl)-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₄FNOS, (IV), 7-fluoro-2-exo-(5-methyl­thio­phen-2-yl)-2,3,4,5-tetra­hy­dro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₄FNOS, (V), 7-chloro-2-exo-(5-methyl­furan-2-yl)-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₄ClNO₂, (VI), 2-exo-(5-methyl­furan-2-yl)-7-trifluoro­meth­oxy-2,3,4,5-tetrahydro-1,4-ep­oxy-1H-1-benzazepine, C₁₆H₁₄F₃NO₃, (VII), 2-exo-(3-methyl­thio­phen-2-yl)-7-trifluoro­meth­oxy-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₆H₁₄F₃NO₂S, (VIII), and 2-exo-(5-nitro­furan-2-yl)-7-trifluoro­meth­oxy-2,3,4,5-tetra­hydro-1,4-ep­oxy-1H-1-benzazepine, C₁₅H₁₁F₃N₂O₅, (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...[pi](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...[pi](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...[pi](arene) hydrogen bond. Comparisons are made with some related compounds.

(2RS,4RS)-7-Fluoro-2-(2-phenyl­eth­yl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine and (2RS,4RS)-7-chloro-2-(2-phenyl­eth­yl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine are isomorphous but not strictly isostructural

(2RS,4RS)-7-Fluoro-2-(2-phenyl­ethyl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C₁₈H₁₈FNO, (I), and (2RS,4RS)-7-chloro-2-(2-phenyl­ethyl)-2,3,4,5-tetra­hydro-1H-1,4-ep­oxy-1-benzazepine, C₁₈H₁₈ClNO, (II), are isomorphous but not strictly isostructural, as the slight differences in the unit-cell dimensions and mol­ecular conformations are sufficient to preclude, in the structure of (I), the direction-specific inter­molecular inter­actions present in the structure of (II), where the mol­ecules are linked into sheets by a combination of C-H...N and C-H...[pi](arene) hydrogen bonds.