Collect. Czech. Chem. Commun.
1987, 52, 696-706
https://doi.org/10.1135/cccc19870696
The crystal and electron structure of O-(2-chloroethyl)-O-isobutyl-O-(2-phenyl-4-methylthio-3-oxo-2H-pyridazine-5-yl) thiophosphate
Viktor Vrábela, František Pavelčíkb, Eleonóra Kellöa, Stanislav Miertuša, Václav Konečnýc and Jan Lokaja
a Department of Analytical Chemistry, Faculty of Chemical Technology, Slovak Institute of Technology, 812 37 Bratislava
b Department of Analytical Chemistry, Faculty of Pharmacy, Comenius University, 800 34 Bratislava
c Research Institute of Chemical Technology, 836 03 Bratislava
Abstract
The crystal structure of the title fungicide was solved by direct methods, using Σ2 relationship and tangent formula. The structure refinement was made by full-matrix least-squares with anisotropic temperature factors to the final R = 0.096 for 1 486 significant reflexions. The compound crystallizes in the orthorhombic system, the space group Pccn. The lattice parameters are a = 1.8719(9), b = 3.0426(33), c = 0.7616(2) nm and Z = 8. The intermolecular interactions of types C-H···Cl and C-H···O are observed between the centrosymmetrically related molecules in the crystal structure. The coordination polyhedron around phosphorus is between trigonal pyramid and tetrahedron. The planes of the phenyl and pyridazine rings are rotated through 70° each other. The electron structure was calculated by semiempirical CNDO/2 method. The calculations revealed the most negative net charges on S(2) and O(1). The value of Wiberg index Iw = 1.08 and the bond distance 0.149 nm show that the bond N(1)-C(5) is simple and is not involved in the conjugation.
