1-Amino-2-methyl-4-(triphenylphosphonio)anthraquinone bromide

Sample Originator: S. M. Khan, Michael B. Hursthouse, Simon J. Coles and D. W. Allen.

C₃₃H₂₅N₁O₂P+ . Br-

InChI=1/C33H25NO2P.Br/c1-22-21-28(29-30(31(22)34)33(36)27-20-12-11-19-26(27)32(29)35)37(23-13-5-2-6-14-23,24-15-7-3-8-16-24)25-17-9-4-10-18-25;/h2-21H,34H2,1H3;

Identification Number:	10.5258/ecrystals/80
Controlled Keywords:	Crystal structures, Catalysis, Phosphonium salts, Stibonium salts, Hypercoordination
Date Created:	08 April 2002
Deposited On:	21 Jan 2008 15:28
Deposited By:	A.N. Admin

Depositor Comments

Metal ion-catalysed replacement of bromine in 1-amino-2-methyl-4-bromoanthraquinone by triphenylphosphine and triphenylstibine occurs readily under mild conditions to give the respective phosphonio- and stibonio-anthraquinone salts, the carbonyl group acting as a coordination template for the metal ion, facilitating replacement of the halogen. The extent to which the Group 15 element may be involved in hypercoordination from the adjacent carbonyl oxygen atom in the ’onium salts has been investigated by X-ray crystallography. Both salts involve considerable distortion of bond angles about the Group 15 atom in the direction of trigonal bipyramidal geometry, with phosphorus–oxygen (2.661 Å) and antimony–oxygen (2.497 Å) distances which are well within the sum of the van der Waals radii. In both structures, the Group 15 element and the adjacent carbonyl oxygen atom are bent out of the plane of the anthraquinone system. However, the extent of out of plane deformation is smaller in the case of the larger antimony atom, suggesting that there is a genuine hypercoordinative interaction which increases as the Group is descended.DOI: 10.1016/S0020-1693(03)00481-X

Data collection parameters

Chemical formula	C33 H25 Br N O2 P
Crystal morphology
Crystal system	Monoclinic
Space group symbol	C2/c
Cell length a	26.860(3)
Cell length b	10.0338(9)
Cell length c	22.976(3)
Cell angle alpha	90.00
Cell angle beta	124.152(11)
Cell angle gamma	90.00
Data collection temperature	120(2)

Refinement results

Solution figure of merit	0.0895
R Factor (Obs)	0.0493
R Factor (All)	0.0726
Weighted R Factor (Obs)	0.1085
Weighted R Factor (All)	0.1219

Citation: Khan, S. M. and Hursthouse, Michael B. and Coles, Simon J. and Allen, D. W. (2002) University of Southampton, Crystal Structure Report Archive. (doi:10.5258/ecrystals/80)
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