Publication

X-ray crystallographic structure of the potent antiplasmodial compound 2,7-dibromocryptolepine acetic acid solvate.

Potter, B.S.
; 
Lisgarten, J.N.
; 
Pitts, J.E.
; 
Palmer, R.A.
; 
Wright, Colin W.
Publication Date
2008
End of Embargo
Supervisor
Keywords
Cryptolepine, Malaria, DNA intercalation, Crystal structure, Antiplasmodial
Rights
Peer-Reviewed
Yes
Open Access status
closedAccess
Accepted for publication
Institution
Department
Awarded
Embargo end date
Collections
Life Sciences Publications
Show all metadata
Additional title
Abstract
The structure of 2,7-dibromocryptolepine acetic acid solvate, C16H11N2Br2 [1.5(C2H4O2)][C2H3O2 -] [0.5H2O], Mr = 460.17, has been determined from X-ray diffraction data. The crystals are monoclinic, space group P21/c with Z = 4 molecules per unit cell and a = 7.3243(3), b = 18.7804(6), c = 15.8306(7) A ° , b = 94.279(1) , Vc = 2171.5(2) A ° , crystal density Dc = 1.667 g/cm3. The structure was determined using direct methods and refined by full-matrix least-squares to a conventional R-index of 0.0496 for 4,908 reflections and 258 parameters. The cryptolepine nucleus of the 2,7-dibromocryptolepine molecule is highly planar and the two Br atoms are in this plane within 0.06 and 0.01 A ° , respectively. The crystal structure is maintained via hydrogen bonding between N(10) in the cryptolepine nucleus and the oxygen of one of the three solvated acetic acid molecules. The acetic acid molecules also form hydrogen bonded chains. Acetic acid B is deprotonated and its two C¿O bond lengths are equivalent, unlike those in A and C. Acetic acid C lies very close to a crystallographic centre of symmetry. To avoid overlap the two repeats cannot exist together and are subject to 50% statistical disorder. O(1C) of this methanol is furthest from the two-fold axis and its occupancy refines to a value of 1.0 and is assumed to exist alternately as a water oxygen hydrogen bonding to methanol O(1C) across the two-fold axis at a distance of 2.775 A ° .
URI
http://hdl.handle.net/10454/4526
Version
No full-text in the repository
Citation
Potter, B. S., Lisgarten, J. N., Pitts, J. E. Palmer, R. A. and Wright, C. W. (2008). X-ray crystallographic structure of the potent antiplasmodial compound 2,7-dibromocryptolepine acetic acid solvate. Journal of Chemical Crystallography, Vol.38, No. 11, pp. 807-813.
Link to publisher’s version
Link to published version
Link to Version of Record
https://doi.org/10.1007/s10870-008-9398-7
Type
Article
Qualification name
Notes