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A new polymorph of physcion.
MedLine Citation:
PMID:  22850859     Owner:  NLM     Status:  In-Data-Review    
The structure of the title compound, 7-methoxy-2-methyl-4,5-dihydroxyanthracene-9,10-dione, C(16)H(12)O(5), was originally reported by Ulický et al. [Acta Cryst. (1991). C47, 1879-1881] in the space group P2(1)2(1)2(1) [polymorph (Io)]. The new polymorph, (Im), crystallizes in the space group P2(1)/c. The molecular structures are closely similar, with both -OH groups forming intramolecular hydrogen bonds to one of the neighbouring quinone O atoms, thus slightly lengthening this C=O bond; the pattern of C-C bond lengths in the ring system is consistent with some contribution from a resonance form with a negative charge at the hydrogen-bonded quinone O atom and an aromatic region around its neighbouring C atoms. The packing of (Im) is simpler than the extensively crosslinked pattern of (Io), with molecular tapes connected by classical (but three-centre) and `weak' hydrogen bonds, parallel to [20-1].
Henning Hopf; Peter G Jones; Eva Goclik; Pauline Aust; Johanna Rödiger
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Publication Detail:
Type:  Journal Article     Date:  2012-07-19
Journal Detail:
Title:  Acta crystallographica. Section C, Crystal structure communications     Volume:  68     ISSN:  1600-5759     ISO Abbreviation:  Acta Crystallogr C     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-08-01     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8305826     Medline TA:  Acta Crystallogr C     Country:  United States    
Other Details:
Languages:  eng     Pagination:  o317-9     Citation Subset:  IM    
Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany.
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