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Insight Into the Intermolecular Factors Responsible for the Z , Z Configuration of Ar–X–N=S=N–X–Ar (X = S, Se) Derivatives in the Solid State
Author(s) -
Tersago Karla,
Bagryanskaya Irina Yu.,
Gatilov Yuri V.,
Gromilov Sergey A.,
Makarov Alexander Yu.,
Mandado Marcos,
Van Alsenoy Christian,
Zibarev Andrey V.,
Blockhuys Frank
Publication year - 2007
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200601024
Subject(s) - chemistry , intramolecular force , intermolecular force , crystallography , crystal structure , stereochemistry , crystal (programming language) , derivative (finance) , crystal engineering , molecule , supramolecular chemistry , organic chemistry , computer science , financial economics , programming language , economics
The molecular and crystal structures of three new derivatives of Ph–S–N=S=N–S–Ph ( 1 ), with 2,4,6‐( tert‐ C 4 H 9 ) 3 C 6 H 2 ( 4 ), C 6 F 5 ( 5 ) and 4‐CF 3 C 6 F 4 ( 6 ) as peripheral rings, respectively, and one new derivative of Ph–Se–N=S=N–Se–Ph ( 2 ), with C 6 F 5 ( 7 ) as peripheral rings, are reported and discussed in connection with those of the two parent structures 1 and 2 and those of the previously studied derivative of 1 containing 4‐ClC 6 H 4 ( 3 ) as peripheral rings. For these seven compounds the Z , Z configuration is the only one of the three theoretically possible configurations observed in the solid state and this configurational preference can not be explained by intramolecular stereoelectronic effects. Calculation of the packing energies and densities for the six most common space groups revealed that the crystal packing of the parent structure 1 in the Z , Z configuration has a systematic preference over the corresponding packing of 1 in the Z , E configuration by 0.3–4.9 kJ mol –1 . As a result, packing forces are most likely responsible for the dominance of the Z , Z configuration of the title compounds in the crystal.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)