Molecular structure of (E)- and (Z)-methylcyanovinyl sulphone in the gas phase and in crystal

Autor:	Jana Podlahová, D. Hnyk, Jaroslav Podlaha, B. Rozsondai, E. Vajda, J. Hašek
Rok vydání:	1990
Předmět:	Steric effects Chemistry Gas electron diffraction Hydrogen bond Organic Chemistry Analytical Chemistry Inorganic Chemistry Crystal Crystallography Molecular geometry Intramolecular force Molecule Conformational isomerism Spectroscopy
Zdroj:	Journal of Molecular Structure. 239:265-279
ISSN:	0022-2860
DOI:	10.1016/0022-2860(90)80220-e
Popis:	The structure of (E)- and (Z)-methylcyanovinyl sulphone has been determined by gas electron diffraction and by X-ray crystallography. Considerably widened bond angles in the Z-isomer indicate steric repulsions across the CC bond. The conformer occurring in the crystal and prevailing in the gas phase has nearly eclipsed CC and SO bonds and is stabilized by an intramolecular hydrogen bond in the E-isomer, and by an attractive interaction, O···C(N) 2.78–2.81 A, in the Z-isomer. Parameters (rg with estimated total errors) SO, SCmean, CC, CN and OSCvinyl, OSCmethyl, CSC, SCC, CCC, OSO in the free E-isomer: 1.437(3), 1.781(4), 1.344(5). 1.165(3) A and 105.2(5), 110.2(2), 102.3(9), 114.9(6), 121.5(7), 121.4(7)°; in the free Z-isomer: 1.437(3), 1.780(4), 1.344(5), 1.168(3) A and 109.6(3), 104.3(3), 108.4(5), 124.7(4), 127.3(7), 119.8(0)°. Crystal data: E-isomer: P1, a=5.798(1), b=6.185(1), c=8.959(2) A, α=102.83(2), β=108.74(2), γ=92.18(2)°, Z=2,ϱm=1.476(7),ϱc=1.480 g cm−3; Z-isomer; P21/c, a=10.613(4), b=16.066(4), c=8.630(2) A, α=90, β=122.14(2), γ=90°, Z=8, ϱm=1.395(4), ϱc=1.398 g cm−3. There is an O⋯H contact of 2.26 A between the two independent molecules in the asymmetric unit of the Z-isomer.
Databáze:	OpenAIRE
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