Acta Crystallographica Section B

Structural Science

Volume 57, Part 6 (December 2001)

Acta Cryst. (2001). B57, 806-814 [doi:10.1107/S0108768101016238]

X-ray investigations of sulfur-containing fungicides. III. Intramolecular forces governing the conformation of a novel orthorhombic polymorph of benzoylmethyl phenyl sulfone, benzoylmethyl 4-chlorophenyl sulfone and benzoylphenylmethyl phenyl sulfone

W. M. Wolf

Abstract: The crystal and molecular structures of three [beta] -ketosulfones: benzoylmethyl phenyl sulfone (I), benzoylmethyl 4-chlorophenyl sulfone (II) and benzoylphenylmethyl phenyl sulfone (III) have been investigated using X-ray analysis and quantum mechanics ab initio calculations. Compound (I) crystallizes in the monoclinic and orthorhombic crystal systems. The crystal structure of the orthorhombic polymorph has not been reported previously. At room temperature and in the presence of daylight the pale yellow orthorhombic crystals undergo transformation to the stable colourless monoclinic polymorph. Hyperconjugative [bold sigma] (S-C1) - [bold pi] ^*(C2=O3) and ^*(S-C1) - (C2=O3) stabilization energies in benzoylmethyl phenyl sulfones are highly dependent on the central dihedral angle [alpha] : S-C1-C2=O3 and are largest for a gauche arrangement, as found in both crystal forms of (I). The electron density distribution in all compounds (I), (II) and (III) is significantly affected by interactions of oxygen lone pairs with non-bonding orbitals of the adjacent S-C1 and C1-C2 bonds. The latter effect is responsible for back-donation of the electron density from O atoms towards the central part of the molecule.

Online 29 November 2001


	Structure factor file (CIF format) (129.4 kbytes) Contains datablock (Io)

	Structure factor file (CIF format) (178.3 kbytes) Contains datablock (Im)

	Structure factor file (CIF format) (111.9 kbytes) Contains datablock (II)

	Structure factor file (CIF format) (185.4 kbytes) Contains datablock (III)

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