Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety
Authors
Lazić, Anita M.
Trišović, Nemanja

Radovanović, Lidija D.

Rogan, Jelena R.

Poleti, Dejan

Vitnik, Željko

Vitnik, Vesna

Ušćumlić, Gordana

Article (Accepted Version)
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A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an imp...ortant role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.
Source:
CrystEngComm, 2017, 19, 3, 469-483Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
- Zero- to Three-Dimensional Nanostructures for Application in Electronics and Renewable Energy Sources: Synthesis, Characterization and Processing (RS-45007)
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
Note:
- This is the peer-reviewed version of the following article: Crystengcomm, 2017, 19, 3, 469-483 https://dx.doi.org/10.1039/C6CE02210C
- http://cer.ihtm.bg.ac.rs/handle/123456789/2204
DOI: 10.1039/c6ce02210c
ISSN: 1466-8033
WoS: 000395439400007
Scopus: 2-s2.0-85010198850
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IHTMTY - JOUR AU - Lazić, Anita M. AU - Trišović, Nemanja AU - Radovanović, Lidija D. AU - Rogan, Jelena R. AU - Poleti, Dejan AU - Vitnik, Željko AU - Vitnik, Vesna AU - Ušćumlić, Gordana PY - 2017 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3002 AB - A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives. PB - Royal Soc Chemistry, Cambridge T2 - CrystEngComm T1 - Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety VL - 19 IS - 3 SP - 469 EP - 483 DO - 10.1039/c6ce02210c ER -
@article{ author = "Lazić, Anita M. and Trišović, Nemanja and Radovanović, Lidija D. and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Ušćumlić, Gordana", year = "2017", abstract = "A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/ or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H... O hydrogen bonds in R22(8) rings, while the CH. O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X...O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H... X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X. O interaction is absent, and along with the C-H. X interactions, these compounds realize an alternative crystal structure with an emphasis on the X. p interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.", publisher = "Royal Soc Chemistry, Cambridge", journal = "CrystEngComm", title = "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety", volume = "19", number = "3", pages = "469-483", doi = "10.1039/c6ce02210c" }
Lazić, A. M., Trišović, N., Radovanović, L. D., Rogan, J. R., Poleti, D., Vitnik, Ž., Vitnik, V.,& Ušćumlić, G.. (2017). Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm Royal Soc Chemistry, Cambridge., 19(3), 469-483. https://doi.org/10.1039/c6ce02210c
Lazić AM, Trišović N, Radovanović LD, Rogan JR, Poleti D, Vitnik Ž, Vitnik V, Ušćumlić G. Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety. in CrystEngComm. 2017;19(3):469-483. doi:10.1039/c6ce02210c .
Lazić, Anita M., Trišović, Nemanja, Radovanović, Lidija D., Rogan, Jelena R., Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Ušćumlić, Gordana, "Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety" in CrystEngComm, 19, no. 3 (2017):469-483, https://doi.org/10.1039/c6ce02210c . .