Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database
Authors
Milovanović, Milan R.Živković, Jelena M.
Ninković, Dragan
Blagojević Filipović, Jelena P.
Vojislavljević-Vasilev, Dubravka
Veljković, Ivana S.
Stanković, Ivana M.
Malenov, Dušan P.
Medaković, Vesna
Veljković, Dušan Ž.
Zarić, Snežana D.
Conference object (Published version)
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In the recent review it was point out that the crystal structures in the Cambridge Structural Database (CSD), collected, have contribute
to various fields of chemical research such as geometries of molecules, noncovalent interactions of molecules, and large assemblies of
molecules. The CSD also contributed to the study and the design of biologically active molecules and the study of gas storage and
delivery [1].
In our group we use analysis of the crystal structures in the CSD to recognize and characterize new types of noncovalent interactions
and to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions,
frequency of the interactions, and preferred geometries of the interactions in the crystal structures. In addition, we perform quantum
chemical calculations to evaluate the energies of the interactions. Based on the calculated potential energy surfaces for the
interactions, we can determine the most stable ge...ometries, as well as stability of various geometries. We also can determine the
interaction energies for the preferred geometries in the crystal structures. In the cases where the most preferred geometries in the
crystal structures are not the most stable geometries at the potential energy surface, one can find significant influence of the
supramolecular structures in the crystals.
Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic
aromatic rings and stacking interactions between two chelate rings. The calculated energies indicate strong stacking interactions of
metal-chelate rings; the stacking of metal-chelate rings is stronger than stacking between two benzene molecules [2]. The data indicate
influence of the metal and ligand type in the metal chelate ring on the strength of the interactions. Our results also indicate strong
stacking interactions of coordinated aromatic rings [3]. Studies of interactions of coordinated water indicate stronger hydrogen bonds
and stronger OH/π interactions of coordinated in comparison to noncoordianted water molecule [4,5]. The calculations on OH/M
interactions between metal ion in square-planar complexes and water molecule indicate that these interactions are among the strongest
hydrogen bonds in any molecular system [6].
The studies on stacking interactions of benzene molecules in the crystal structures in the CSD show preference for interactions at large
horizontal displacements, while high level quantum chemical calculations indicate significantly strong interactions at large offsets; the
energy is 70% of the strongest stacking geometry [7].
Keywords:
Cambridge Structural Database / noncovalent interactions / ab initio calculations / aromatic molecules / metal complexesSource:
25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021, 2021, A77, C192-Publisher:
- Wiley
Funding / projects:
- Noncovalent interactions of pi-systems and their role in molecular recognition (RS-MESTD-Basic Research (BR or ON)-172065)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200288 (Innovation Center of the Faculty of Chemistry) (RS-MESTD-inst-2020-200288)
Collections
Institution/Community
Inovacioni centar / Innovation CentreTY - CONF AU - Milovanović, Milan R. AU - Živković, Jelena M. AU - Ninković, Dragan AU - Blagojević Filipović, Jelena P. AU - Vojislavljević-Vasilev, Dubravka AU - Veljković, Ivana S. AU - Stanković, Ivana M. AU - Malenov, Dušan P. AU - Medaković, Vesna AU - Veljković, Dušan Ž. AU - Zarić, Snežana D. PY - 2021 UR - http://cherry.chem.bg.ac.rs/handle/123456789/5275 UR - https://iucr25.org/ AB - In the recent review it was point out that the crystal structures in the Cambridge Structural Database (CSD), collected, have contribute to various fields of chemical research such as geometries of molecules, noncovalent interactions of molecules, and large assemblies of molecules. The CSD also contributed to the study and the design of biologically active molecules and the study of gas storage and delivery [1]. In our group we use analysis of the crystal structures in the CSD to recognize and characterize new types of noncovalent interactions and to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures. In addition, we perform quantum chemical calculations to evaluate the energies of the interactions. Based on the calculated potential energy surfaces for the interactions, we can determine the most stable geometries, as well as stability of various geometries. We also can determine the interaction energies for the preferred geometries in the crystal structures. In the cases where the most preferred geometries in the crystal structures are not the most stable geometries at the potential energy surface, one can find significant influence of the supramolecular structures in the crystals. Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic aromatic rings and stacking interactions between two chelate rings. The calculated energies indicate strong stacking interactions of metal-chelate rings; the stacking of metal-chelate rings is stronger than stacking between two benzene molecules [2]. The data indicate influence of the metal and ligand type in the metal chelate ring on the strength of the interactions. Our results also indicate strong stacking interactions of coordinated aromatic rings [3]. Studies of interactions of coordinated water indicate stronger hydrogen bonds and stronger OH/π interactions of coordinated in comparison to noncoordianted water molecule [4,5]. The calculations on OH/M interactions between metal ion in square-planar complexes and water molecule indicate that these interactions are among the strongest hydrogen bonds in any molecular system [6]. The studies on stacking interactions of benzene molecules in the crystal structures in the CSD show preference for interactions at large horizontal displacements, while high level quantum chemical calculations indicate significantly strong interactions at large offsets; the energy is 70% of the strongest stacking geometry [7]. PB - Wiley C3 - 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021 T1 - Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database VL - A77 SP - C192 UR - https://hdl.handle.net/21.15107/rcub_cherry_5275 ER -
@conference{ author = "Milovanović, Milan R. and Živković, Jelena M. and Ninković, Dragan and Blagojević Filipović, Jelena P. and Vojislavljević-Vasilev, Dubravka and Veljković, Ivana S. and Stanković, Ivana M. and Malenov, Dušan P. and Medaković, Vesna and Veljković, Dušan Ž. and Zarić, Snežana D.", year = "2021", abstract = "In the recent review it was point out that the crystal structures in the Cambridge Structural Database (CSD), collected, have contribute to various fields of chemical research such as geometries of molecules, noncovalent interactions of molecules, and large assemblies of molecules. The CSD also contributed to the study and the design of biologically active molecules and the study of gas storage and delivery [1]. In our group we use analysis of the crystal structures in the CSD to recognize and characterize new types of noncovalent interactions and to study already known noncovalent interactions. Based on the data from the CSD we can determine existence of the interactions, frequency of the interactions, and preferred geometries of the interactions in the crystal structures. In addition, we perform quantum chemical calculations to evaluate the energies of the interactions. Based on the calculated potential energy surfaces for the interactions, we can determine the most stable geometries, as well as stability of various geometries. We also can determine the interaction energies for the preferred geometries in the crystal structures. In the cases where the most preferred geometries in the crystal structures are not the most stable geometries at the potential energy surface, one can find significant influence of the supramolecular structures in the crystals. Using this methodology our group recognized stacking interactions of planar metal-chelate rings; stacking interactions with organic aromatic rings and stacking interactions between two chelate rings. The calculated energies indicate strong stacking interactions of metal-chelate rings; the stacking of metal-chelate rings is stronger than stacking between two benzene molecules [2]. The data indicate influence of the metal and ligand type in the metal chelate ring on the strength of the interactions. Our results also indicate strong stacking interactions of coordinated aromatic rings [3]. Studies of interactions of coordinated water indicate stronger hydrogen bonds and stronger OH/π interactions of coordinated in comparison to noncoordianted water molecule [4,5]. The calculations on OH/M interactions between metal ion in square-planar complexes and water molecule indicate that these interactions are among the strongest hydrogen bonds in any molecular system [6]. The studies on stacking interactions of benzene molecules in the crystal structures in the CSD show preference for interactions at large horizontal displacements, while high level quantum chemical calculations indicate significantly strong interactions at large offsets; the energy is 70% of the strongest stacking geometry [7].", publisher = "Wiley", journal = "25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021", title = "Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database", volume = "A77", pages = "C192", url = "https://hdl.handle.net/21.15107/rcub_cherry_5275" }
Milovanović, M. R., Živković, J. M., Ninković, D., Blagojević Filipović, J. P., Vojislavljević-Vasilev, D., Veljković, I. S., Stanković, I. M., Malenov, D. P., Medaković, V., Veljković, D. Ž.,& Zarić, S. D.. (2021). Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021 Wiley., A77, C192. https://hdl.handle.net/21.15107/rcub_cherry_5275
Milovanović MR, Živković JM, Ninković D, Blagojević Filipović JP, Vojislavljević-Vasilev D, Veljković IS, Stanković IM, Malenov DP, Medaković V, Veljković DŽ, Zarić SD. Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database. in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021. 2021;A77:C192. https://hdl.handle.net/21.15107/rcub_cherry_5275 .
Milovanović, Milan R., Živković, Jelena M., Ninković, Dragan, Blagojević Filipović, Jelena P., Vojislavljević-Vasilev, Dubravka, Veljković, Ivana S., Stanković, Ivana M., Malenov, Dušan P., Medaković, Vesna, Veljković, Dušan Ž., Zarić, Snežana D., "Study of noncovalent interactions using crystal structure data in the Cambridge Structural Database" in 25th Congress and General Assembly of the International Union of Crystallography, Prague, Czech Republic, August 2021, A77 (2021):C192, https://hdl.handle.net/21.15107/rcub_cherry_5275 .