Fluoren-9-one oxime.

Bernhard Bugenhagen,Thies Thiemann,Yosef Al Jasem,Mariam Al-Azani

doi:10.1107/s1600536814002669

Abstract

In the title molecule, C13H9NO, the fluorene system and the oxime group non-H atoms are essentially coplanar, with a maximum deviation from the fluorene mean plane of 0.079 (2) Å for the oxime O atom. A short intramolecular C—H⋯O generates an S(6) ring. In the crystal, molecules related by a twofold screw axis are connected by O—H⋯N hydrogen bonds, forming [100] chains Within these chains, molecules related by a unit translation along [100] show π–π stacking interactions between their fluorene ring systems with an interplanar distance of 3.347 (2) Å. The dihedral angle between the fluorene units of adjacent molecules along the helix is 88.40 (2)°. There is a short C—H⋯π contact between the fluorene groups belonging to neighbouring chains.

Highlights

In the title molecule, C13H9NO, the fluorene system and the oxime group non-H atoms are essentially coplanar, with a maximum deviation from the fluorene mean plane of
Hydrogen bonds, forming [100] chains Within these chains, molecules related by a unit translation along [100] show
There is a short C—H contact between the fluorene groups belonging to neighbouring chains

Summary

Data collection

R factor = 0.029; wR factor = 0.075; data-to-parameter ratio = 13.9. Absolute structure: Flack parameter determined using 735 quotients [(I+)(I)]/[(I+)+(I)]. Molecules related by a twofold screw axis are connected by O—H N hydrogen bonds, forming [100] chains Within these chains, molecules related by a unit translation along [100] show – stacking interactions between their fluorene ring systems with an interplanar distance of 3.347 (2) Å. The dihedral angle between the fluorene units of adjacent molecules along the helix is 88.40 (2). There is a short C—H contact between the fluorene groups belonging to neighbouring chains. Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within OLEX2.

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Special details