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The Structure of Bilirubin

R. Bonnett, J. E. Davies, M. B. Hursthouse and G. M. Sheldrick
Proceedings of the Royal Society of London. Series B, Biological Sciences
Vol. 202, No. 1147 (Jun. 23, 1978), pp. 249-268
Published by: Royal Society
Stable URL: http://www.jstor.org/stable/77251
Page Count: 20
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The Structure of Bilirubin
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Abstract

Crystals of bilirubin are triclinic, space group P1̄ with cell dimensions a = 19.439, b = 11.707, c = 15.500 angstrom,† , α = 97.19, β = 100.22, γ = 118.20 degrees, Z = 4. The structure was solved by direct methods incorporating information derived from reflexion quartets and by using a set of diffractometer data containing 1408 reflexions with Fobs≥ 3σ (Fobs). The structure was refined with bond-length constraints to a final R of 0.125 by using a set of microdensitometer-measured photographic data containing 1323 unique observed reflexions. Both data sets were collected from a matured crystal whose diffraction pattern had improved considerably during a period of several weeks. Bilirubin is shown to have the Z configuration at both the C5 and C15 bridges. The two independent molecules of bilirubin in the crystal structure have very similar 'ridge tile' conformations: rings (A + B) and rings (C + D) form two good planes with an interplanar angle of approximately 97 degrees and the molecule is stabilized by six intramolecular hydrogen bonds. There is no evidence for any intermolecular hydrogen bonding. Observed bond lengths suggest that bilirubin can be regarded as a 2,2′-dipyrrolylmethane with conjugating substituents at the α positions. When freshly prepared, most crystals of bilirubin have reflexions hkl (h odd) diffuse: this observation is discussed in terms of the molecular conformation of bilirubin and the particular packing arrangement which these molecules adopt in the crystal structure.

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