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)
[ doi:10.1107/S010827011202447X/fg3250Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format)
[ doi:10.1107/S010827011202447X/fg3250IIsup3.hkl ]
Contains datablock {vcif ERROR: unable to open file /journals/webproduction/sites/cjo-test/c/issues/2012/07/00/fg3250/fg3250IIsup3.hkl - exiting}

hkldisplay filedownload file

Structure factor file (CIF format)
[ doi:10.1107/S010827011202447X/fg3250IIIsup4.hkl ]
Contains datablock {vcif ERROR: unable to open file /journals/webproduction/sites/cjo-test/c/issues/2012/07/00/fg3250/fg3250IIIsup4.hkl - exiting}


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster