TY - JOUR
T1 - A comprehensive analysis of the molecular packing in the crystal of N2-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine and in its 1:1 ethanol solvate
AU - Tan, Sang Loon
AU - Shahari, Muhammad Syafiq Bin
AU - Junaid, Ahmad
AU - Dolzhenko, Anton V.
AU - Tiekink, Edward R.T.
N1 - Funding Information:
This work was supported by the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme (Grant no. FRGS/1/2020/STG04/MUSM/02/2 ). Sunway University Sdn Bhd is gratefully acknowledged for support of research facilities and funding (GRTIN-RRO-56-2022). The authors also would like to thank Robust HPC Sdn Bhd for the provision of access to the high-performance computing facilities and for providing technical support services.
Publisher Copyright:
© 2023 Elsevier B.V.
PY - 2024/4/15
Y1 - 2024/4/15
N2 - The crystal and molecular structures of N2-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine (1) and its 1:1 ethanol solvate (1.EtOH) are reported. The triazine molecule is substituted by amino, 3,4,5-trimethoxyphenyl and 4-chlorophenylamino groups. The experimental molecular structures are like each other and similar to the calculated gas-phase structure. The molecular packing is distinct in that a twisted supramolecular tape is formed in 1 featuring amino-N[sbnd]H···N (triazine) hydrogen bonds. Similar hydrogen-bonding is evident in 1.EtOH but occurs between centrosymmetrically related molecules. The solvent ethanol molecule plays a pivotal role in the packing by participating amino-N[sbnd]H···O (ethanol) and ethanol-O[sbnd]H···O (methoxy) hydrogen bonds within a jagged supramolecular tape. Many additional non-covalent interactions between the tapes are noted in the three-dimensional molecular packing. These and the conventional hydrogen-bonding interactions have been evaluated by a variety of computational chemistry techniques. The greater crystal lattice energy calculated for 1.EtOH is ascribed to the stability afforded by the additional hydrogen-bonding involving the ethanol molecule and the considerably greater role of π···π stacking interactions in the molecular packing.
AB - The crystal and molecular structures of N2-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,5-triazine-2,4-diamine (1) and its 1:1 ethanol solvate (1.EtOH) are reported. The triazine molecule is substituted by amino, 3,4,5-trimethoxyphenyl and 4-chlorophenylamino groups. The experimental molecular structures are like each other and similar to the calculated gas-phase structure. The molecular packing is distinct in that a twisted supramolecular tape is formed in 1 featuring amino-N[sbnd]H···N (triazine) hydrogen bonds. Similar hydrogen-bonding is evident in 1.EtOH but occurs between centrosymmetrically related molecules. The solvent ethanol molecule plays a pivotal role in the packing by participating amino-N[sbnd]H···O (ethanol) and ethanol-O[sbnd]H···O (methoxy) hydrogen bonds within a jagged supramolecular tape. Many additional non-covalent interactions between the tapes are noted in the three-dimensional molecular packing. These and the conventional hydrogen-bonding interactions have been evaluated by a variety of computational chemistry techniques. The greater crystal lattice energy calculated for 1.EtOH is ascribed to the stability afforded by the additional hydrogen-bonding involving the ethanol molecule and the considerably greater role of π···π stacking interactions in the molecular packing.
KW - 1,3,5-triazines
KW - Computational chemistry
KW - Hirshfeld surface analysis
KW - Non-covalent interactions
KW - X-ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=85182503674&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2023.137449
DO - 10.1016/j.molstruc.2023.137449
M3 - Article
AN - SCOPUS:85182503674
SN - 0022-2860
VL - 1302
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 137449
ER -