Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 8 (August 2012)


organic compounds



ku3066 scheme

Acta Cryst. (2012). C68, o288-o293    [ doi:10.1107/S0108270112025620 ]

Supramolecular networks in (9-fluoro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol and its 9-chloro analogue at 100 K

P. Rajalakshmi, N. Srinivasan, R. V. Krishnakumar, I. A. Razak and M. M. Rosli

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\overline{1} 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-H...O and C-H...O interactions in (I), and the absence of C-H...Cl and the presence of O-H...O and C-H...O interactions in (II). However, the geometry of the synthons formed by the O-H...N and O-H...X (X = F or Cl) interactions observed in the constitution of the supramolecular networks of both (I) and (II) remains similar. Also, C-H...O 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


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Chemical Markup Language (CML) file (4.3 kbytes)
[ doi:10.1107/S0108270112025620/ku3066Isup4.cml ]
Supplementary material


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Chemical Markup Language (CML) file (4.3 kbytes)
[ doi:10.1107/S0108270112025620/ku3066IIsup5.cml ]
Supplementary material


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