Conformational analysis: crystallographic, molecular mechanics and quantum chemical studies of C--H...O hydrogen bonding in the flexible bis(nosylate) derivative of catechol

Acta Crystallographica. Section B, Structural Science
Orde Q Munro, Lynette Mariah

Abstract

The single-crystal X-ray diffraction analysis of 2-[[(4-nitrophenoxy)sulfonyl]oxy]phenyl 4-nitrophenyl sulfate (4) reveals that an interesting intermolecular or extended structure (a one-dimensional hydrogen-bonded polymer) is formed because of pairs of intermolecular (aryl)C--H...O(nitro) hydrogen bonds between the C(2) symmetry monomer units. The axis of the hydrogen-bonded polymer runs co-linear with the [101] face diagonal of the monoclinic unit cell. Molecular mechanics calculations using a modified version of the MM+ force field and a random conformational search algorithm have been used to locate the important low-energy in vacuo conformations of (4). The MM-calculated conformation of (4) that most closely matches the X-ray structure lies some 26.5 kJ mol(-1) higher in energy than the global minimum-energy conformation, consistent with the notion that the crystallographically observed molecular architecture of (4) is a local energy minimum in the absence of its crystal lattice environment. Since the X-ray conformation of (4) was correctly calculated only when all of the neighbouring molecules in the crystal lattice were included in the simulation, hydrogen bonding and other non-bonded interactions in the crystal lattice ...Continue Reading

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