Issue 12, 1972

Molecular packing modes. Part V. Crystal and molecular structures of fumaramic acid

Abstract

The crystal structure of the title compound has ben solved from X-ray diffractometer data by direct methods and refined by least-squares to R 0·038 for 1182 independent reflections. Crystals are monoclinic, space group P21, with Z= 2 in a unit cell of dimensions: a= 7·367(1), b= 9·041(1), c= 3·742(1)Å, β= 99·39(1)°. The mean σ for bond lengths not involving hydrogen is 0·002 Å.

The hydrogen-bond network is two-dimensional. The amide and carboxy-groups of molecules related by translation form cyclic hydrogen-bonded (asymmetric) pairs (OH ⋯ O, 2·660; NH ⋯ O, 2·838 Å) generating chains which are interlinked, along the 21 axis, by NH ⋯ O (2·935 Å) bonds. The conformations of the groups C:C·C(NH2):O and C:C·C(OH):O are syn-planar, in contrast to the antiplanar C:C·C:O arrangements in the α- and β-forms of fumaric acid.

The bond lengths are: C[double bond, length half m-dash]C 1·320, C(OH)–C 1·497, C(NH2)–C 1·486, C(OH)[double bond, length as m-dash]O 1·209, C(NH2)[double bond, length as m-dash]O 1·247, C–OH 1·310, and C–NH2 1·323 Å.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1972, 1758-1763

Molecular packing modes. Part V. Crystal and molecular structures of fumaramic acid

V. Benghiat, H. W. Kaufman, L. Leiserowitz and G. M. J. Schmidt, J. Chem. Soc., Perkin Trans. 2, 1972, 1758 DOI: 10.1039/P29720001758

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements