Competing and directing interactions in new phosphoramide/thiophosphoramide structures: energy considerations and evidence for CHMIDLINE HORIZONTAL ELLIPSISHC contacts and aliphatic-aromatic stacking

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Authors	HOSSEINPOOR Saeed POURAYOUBI Mehrdad ABRISHAMI Mozhgan SOBATI Marjan AHMADABAD Fatemeh Karimi SABBAGHI Fahimeh NEČAS Marek DUSEK Michal KUCERAKOVA Monika KAUR Manpreet
Year of publication	2023
Type	Article in Periodical
Magazine / Source	CrystEngComm
MU Faculty or unit	Faculty of Science
Citation
Web	https://pubs.rsc.org/en/content/articlelanding/2023/CE/D3CE00204G
Doi	http://dx.doi.org/10.1039/d3ce00204g
Keywords	HYDROGEN-BOND PATTERNS; PHOSPHORIC TRIAMIDES; DATABASE ANALYSIS
Description	Supramolecular aggregates, driven by different molecular functionalities and crystal forces, are studied in new phosphoramide and thiophosphoramide structures (C6H5O)(2)P(O)(2-NHC5H4N) (I), (4-Cl-C6H4O)P(O)(NHC6H11)(2) (II), (4-Cl-C6H4O)P(O)(N(CH3)C6H11)(2) (III), P(S)(NHC(CH3)(3))(3) (IV), and P(S)(3-NHC5H4N)(3) (V). DHMIDLINE HORIZONTAL ELLIPSISA (D = N, C; A = N, O, S) hydrogen bonds, contacts related to the ring stacking (CHMIDLINE HORIZONTAL ELLIPSISp/sMIDLINE HORIZONTAL ELLIPSISp and pMIDLINE HORIZONTAL ELLIPSISp) and some other weak interactions are the structural elements inspected. The techniques/methods used are X-ray crystallography, QTAIM, NCI, 2D fingerprint plots, and lattice energy calculations, complemented by spectroscopic approaches for some additional investigations. A comparison is made with selected analogous structures from the Cambridge Structural Database (CSD). Determinative roles of stronger hydrogen bonds and competition between weaker hydrogen bonds (mostly having dispersion characteristics) are addressed as well as the cyclohexylMIDLINE HORIZONTAL ELLIPSISarene (sMIDLINE HORIZONTAL ELLIPSISp) stacking with pronounced CHMIDLINE HORIZONTAL ELLIPSISp interactions. When the strength and specificity of the hydrogen bonds decrease, the molecules can form a denser packing, and the role of CHMIDLINE HORIZONTAL ELLIPSISHC interactions becomes prominent. Despite their weakness, such interactions together make the bulk of the crystal stabilizing forces.
Related projects:	Czech Infrastructure for Integrative Structural Biology