The structure of the title compound, C 9 H 12 O 4 , contains two independent molecules in the asymmetric unit, with an unusually strong twist around the norbornane C2ÐC3 bond.
Norbornane-exo-cis-2,3-dicarboxylic acid
✍ Scribed by Batsanov, Andrei S. ;Hesselink, Joanna L.
- Publisher
- International Union of Crystallography
- Year
- 2002
- Tongue
- English
- Weight
- 172 KB
- Volume
- 58
- Category
- Article
- ISSN
- 1600-5368
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✦ Synopsis
Both carboxyl groups in the title molecule, C 9 H 12 O 4 , have gauche orientations [relative to the (HOOCÐ)CÐC(Ð COOH) bond] and participate in hydrogen bonds, linking the molecules into an in®nite chain.
Experimental
Hydrogen was introduced to a stirred mixture of (II) (0.65 g, 4 mmol), palladium on carbon (5% Pd, 100 mg) and acetic acid (10 ml). The catalyst was ®ltered off and the solvent removed using a rotary evaporator. The product was recrystallized from doubly distilled water, giving colourless crystalline (I) in 88% yield (0.58 g,
📜 SIMILAR VOLUMES
Single-crystal X-ray study T = 150 K Mean '(C±C) = 0.003 A Ê Disorder in main residue R factor = 0.049 wR factor = 0.102 Data-to-parameter ratio = 12.1 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
The crystal structure of the title compound, C 9 H 10 O 4 , contains in®nite hydrogen-bonded chains of molecules. The norbornene skeleton is slightly twisted.
Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.031 wR factor = 0.110 Data-to-parameter ratio = 9.7 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.002 A Ê R factor = 0.046 wR factor = 0.131 Data-to-parameter ratio = 12.1 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
In the title complex, 2C 9 H 10 O 4 ÁC 8 H 12 N 2 , there is an inversion centre at the centre of the 2,3,5,6-tetramethylpyrazine molecule, which is linked to two endo-norbornene-cis-5,6-dicarboxylic acid molecules via O-HÁ Á ÁN hydrogen bonds. In the crystal structure, O-HÁ Á ÁO and O-HÁ Á ÁN hydro