Acta Cryst. (2012). C68, o288-o293 [ doi:10.1107/S0108270112025620 ]
Abstract: The title compounds, (9-fluoro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C11H8FNO3, (I), and (9-chloro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C11H8ClNO3, (II), crystallize in the orthorhombic space group Pbca with Z' = 1 and the triclinic space group P
with Z' = 6, respectively. The simple replacement of F by Cl in the main molecular scaffold of (I) and (II) results in significant differences in the intermolecular interaction patterns and a corresponding change in the point-group symmetry from D2h to Ci = S2. These striking differences are manifested through the presence of C-H
F and the absence of O-HO and C-HO interactions in (I), and the absence of C-HCl and the presence of O-HO and C-HO interactions in (II). However, the geometry of the synthons formed by the O-HN and O-HX (X = F or Cl) interactions observed in the constitution of the supramolecular networks of both (I) and (II) remains similar. Also, C-HO interactions are not preferred in the presence of F in (I), while they are much preferred in the presence of Cl in (II).
Formula: C11H8FNO3 and C11H8ClNO3
 |   Structure factor file (CIF format) (148.1 kbytes) |
| Structure factor file (CIF format) (1046.4 kbytes) |
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