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Synthesis, crystal structure, hydrogen bonding interactions analysis of novel acyl thiourea derivative
Author(s) -
Zhang Xing,
Du Xiaoli,
Song Jirong,
Huang Jie
Publication year - 2020
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.4016
Subject(s) - chemistry , hydrogen bond , crystallography , van der waals force , stacking , crystal structure , intramolecular force , molecule , orthorhombic crystal system , intermolecular force , thiourea , non covalent interactions , crystal (programming language) , stereochemistry , organic chemistry , computer science , programming language
The N ‐(p‐methoxybenzoyl)‐ N ′‐(2,4‐dinitrophenyl amino)thiourea has been synthesized and characterized by FT‐IR, 1 H NMR, and elemental analyses techniques. Also, its molecular structure was determined by single‐crystal X‐ray diffraction. It revealed that the title compound crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell, space group Pna2(1) with a = 18.857(5) Å, b = 8.148(2) Å, c = 22.443(6) Å, β = 90.00°, C 15 H 13 N 5 O 6 S, M r = 391.36, V = 3448.2(15) Å 3 , Z = 8, D c = 1.508 g·cm −1 , F (000) = 1616, μ = 0.233 mm −1 , S = 1.06, the final R = 0.0626, and wR ( I > 2ϭ( I )) = 0.1392. Intramolecular NH … N, CH … N, and NH … O hydrogen bonds indicate that the molecule conformation was mostly planar. Crystal structure stacking through the NH … O, CH … O, and NH … S hydrogen bonds, and two π … π interactions arrangement revealed their conspicuous role in the stabilization of the molecular structure. The type and nature of intermolecular interactions in the crystal structure were investigated by Hirshfeld surfaces and their associated two‐dimensional fingerprint plots. Furthermore, shape index and curvedness surfaces further confirmed π … π stacking interactions with different features of molecule A and B . More importantly, the reduced density gradient (RDG) function provides a real‐space function for discussing noncovalent interactions (NCI) in title compound, including van der Waals interactions and CH … π contacts in addition to hydrogen bonding interactions within molecule.