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ORTEP-III (Burnett, 1996) drawing
Wortmannin is isolated from Penicillium wortmanni and is a potent inhibitor of phosphatidylinositol 3-kinase (PI 3-kinase). The electrophilic 21-site makes a covalent linkage with the enzyme and the inhibition of PI 3-kinase is irreversible. PI 3-kinase mediates several intracellular signaling pathways, and wortmannin has been focused as a probe to understand the structural requirements necessary for PI 3-kinase inhibition. Two types of structure has been reported for wortmannin; one is orthorhombic crystal and space group P2121212, the other is a 21-methylated analogue and monoclinic, P21. This crystal is a polymorphic with monoclinic C2.
When the minimum van der Waals radii for carbon, oxygen and hydrogen atoms are considered approximately as 1.5, 1.7 and 1.2 Ang respectively, a short contact is found at C21...O21. The distance between H21 and O21 atoms is about 0.5 Ang below the sum of the van der Waals radii of hydrogen and oxygen (=2.7 Ang. and it could be defined as the C-H...O hydrogen bond.

Paper: Polymorphism and C-H...O interactions of Wortmannin, a Phosphatidylinositol 3-Kinase Inhibitor
Mitsunobu DOI, Toshimasa ISHIDA, Akira TERASHIMA, Taizo TANIGUCHI, Masahiro SASAKI and Chikako TANAKA
Analytical Sciences (1998) 14, 1191-2.

X-Ray Data Summary

formulaC9 H10 F N O4 + H2O
space groupP21/c
Cell Crystal
a (Ang) 10.626(3)description needle
b (Ang) 7.482(3) colour Colorless
c (Ang) 13.065(4)size (mm) 0.5x0.09x0.09
alpha (deg)90.0 Dx (g/ml) 1.553
beta (deg)106.23(2)F(000) 488
gamma (deg)90.0 mu(CuKa) 1.206
V (Ang^3) 997.4(6)
Z 4
Refinement Diffrn measurement
Flack device type Rigaku AFC5R/RU-200
parameters 147decay 0.7 %
restraints 0 index limit -12-h-12,-8-k-0,-15-L-15
R_factor_all 0.0592theta (deg.) 4.33 - 65.58
R_factor_gt 0.0453total reflections 3239 include Friedel pairs
wR_factor_ref0.1321reflections(obs) 1393 .gt. 2sigma(I)
wR_factor_gt 0.1186Structure
shift/su_max lt.0.001 solution SHELXS-97
shift/su_mean lt.0.001 refinement SHELXL-97

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Date: Jly.1998