Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 7 (July 2012)


organic compounds



fg3250 scheme

Acta Cryst. (2012). C68, o253-o256    [ doi:10.1107/S010827011202447X ]

Cyclic imides and an open-chain amide carb­oxy­lic acid from the facile reaction of cis-cyclo­hexane-1,2-car­boxy­lic anhydride with the isomeric mono­fluoro­anilines

G. Smith and U. D. Wermuth

Abstract: The structures of the cyclic imides cis-2-(2-fluoro­phenyl)-3a,4,5,6,7,7a-hexa­hydro­iso­in­dole-1,3-dione, C14H14FNO2, (I), and cis-2-(4-fluoro­phenyl)-3a,4,5,6,7,7a-hexa­hydro­isoindoline-1,3-dione, C14H14FNO2, (III), and the open-chain amide acid rac-cis-2-[(3-fluoro­phenyl)­carbamoyl]­cyclo­hexane-1-carb­oxy­lic acid, C14H16FNO3, (II), are reported. Cyclic imides (I) and (III) are conformationally similar, with comparable ring rotations about the imide N-Car bond [the dihedral angles between the benzene ring and the five-membered isoindole ring are 55.40 (8)° for (I) and 51.83 (7)° for (III)]. There are no formal inter­molecular hydrogen bonds involved in the crystal packing of either (I) or (III). With the acid (II), in which the meta-related F-atom substituent is rotationally disordered (0.784:0.216), the amide group lies slightly out of the benzene plane [the inter­planar dihedral angle is 39.7 (1)°]. Inter­molecular amide-carboxyl N-H...O hydrogen-bonding inter­actions between centrosymmetrically related mol­ecules form stacks extending down b, and these are linked across c by carboxyl-amide O-H...O hydrogen bonds, giving two-dimensional layered structures which lie in the (011) plane. The structures reported here represent examples of com­pounds analogous to the phthalimides or phthalanilic acids and have little precedence in the crystallographic literature.

Formula: C14H14FNO2, C14H16FNO3 and C14H14FNO2


hkldisplay filedownload file

Structure factor file (CIF format) (110.9 kbytes)
[ doi:10.1107/S010827011202447X/fg3250Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (120.3 kbytes)
[ doi:10.1107/S010827011202447X/fg3250IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (113.7 kbytes)
[ doi:10.1107/S010827011202447X/fg3250IIIsup4.hkl ]
Contains datablock III


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