Crystal structure of (2Z)-(3,3-dimethyl-3,4-dihydroisoquinolin- 1(2H)-ylidene)nitrosoacetonitrile
- Authors: Polyakova E.I.1, Polyakova I.N.2, Davydov V.V.1, Ryabov M.A.1, Sergienko V.S.2, Shklyaev Y.V.3
-
Affiliations:
- Peoples’ Friendship University of Russia
- Kurnakov Institute of General and Inorganic Chemistry
- Institute of Technical Chemistry, Ural Branch
- Issue: Vol 62, No 4 (2017)
- Pages: 566-571
- Section: Structure of Organic Compounds
- URL: https://journals.rcsi.science/1063-7745/article/view/191143
- DOI: https://doi.org/10.1134/S1063774517040162
- ID: 191143
Cite item
Abstract
The crystal structure of (2Z)-(3,3-dimethyl-3,4-dihydroisoquinolin-1(2Н)-ylidene)nitrosoacetonitrile is determined (T = 150 K, R1 = 0.0435). The compound crystallizes as the E-cis and Z-cis isomers of the nitroso tautomer. Two independent molecules differ in the rotation of the nitroso group about the С–С bond between the dihydroisoquinoline group and the substituent. Analysis of bond lengths reveals their conjugation and prevailing contribution of the zwitter-ionic structures with the positive charge located on the isoquinoline fragment and the negative charge located on the substituent. Molecules having E and Z conformations are connected by the N–H···O hydrogen bond (N···O 2.922(3) Å) into dimers. The N–H group of the other molecule forms the intramolecular N–H···O hydrogen bond (N···O 2.544(3) Å) which closes a sixmembered cycle. Electronic absorption spectra are studied, and quantum-chemical modeling of the compound is performed.
About the authors
E. I. Polyakova
Peoples’ Friendship University of Russia
Author for correspondence.
Email: alania1980@mail.ru
Russian Federation, Moscow, 117198
I. N. Polyakova
Kurnakov Institute of General and Inorganic Chemistry
Email: alania1980@mail.ru
Russian Federation, Moscow, 119991
V. V. Davydov
Peoples’ Friendship University of Russia
Email: alania1980@mail.ru
Russian Federation, Moscow, 117198
M. A. Ryabov
Peoples’ Friendship University of Russia
Email: alania1980@mail.ru
Russian Federation, Moscow, 117198
V. S. Sergienko
Kurnakov Institute of General and Inorganic Chemistry
Email: alania1980@mail.ru
Russian Federation, Moscow, 119991
Yu. V. Shklyaev
Institute of Technical Chemistry, Ural Branch
Email: alania1980@mail.ru
Russian Federation, Perm, 614990