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C—Br…S halogen bonds in novel thiourea N ‐oxide cocrystals: analysis of energetic and QTAIM parameters
Author(s) -
Wzgarda-Raj Kinga,
Rybarczyk-Pirek Agnieszka J.,
Wojtulewski Sławomir,
Palusiak Marcin
Publication year - 2020
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229620000947
Subject(s) - halogen , chemistry , synthon , molecule , substituent , thiourea , atoms in molecules , crystallography , monoclinic crystal system , hydrogen bond , halogen bond , bromine , oxide , crystal structure , computational chemistry , stereochemistry , organic chemistry , alkyl
Cocrystals of thiourea with 4‐nitropyridine N ‐oxide, C 5 H 4 N 2 O 3 ·2CH 4 N 2 S, ( I ), and 3‐bromopyridine N ‐oxide, C 5 H 4 BrNO·CH 4 N 2 S, ( II ), crystallize in the monoclinic space group P 2 1 / c . In the crystals, molecules of both components are linked by N—H…O hydrogen bonds, creating R 2 1 (6) synthons. The bromine substituent of the N ‐oxide component in ( II ) is a centre for C—Br…S halogen bonding to the thiourea molecule. Computations based on quantum chemistry methods (quantum theory of atoms in molecules, QTAIM) and atoms in molecules (AIM) theory were performed for a more detailed description of the observed type of halogen‐bonding interaction.