Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan
The title furan bis(imine) compound, 2,5-bis[(4-fluorophenyl)iminomethyl]furan, C18H12F2N2O, was synthesized by condensation of 2,5-furandicarboxaldehyde with two equivalents of 4-fluoroaniline. The molecular structure consists of a central furan ring symmetrically bound to nearly coplanar iminometh...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2025-07-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | https://journals.iucr.org/paper?S2056989025005006 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1839637022327701504 |
|---|---|
| author | Moira K. Lauer Gary J. Balaich Scott T. Iacono Nathan J. Weeks |
| author_facet | Moira K. Lauer Gary J. Balaich Scott T. Iacono Nathan J. Weeks |
| author_sort | Moira K. Lauer |
| collection | DOAJ |
| description | The title furan bis(imine) compound, 2,5-bis[(4-fluorophenyl)iminomethyl]furan, C18H12F2N2O, was synthesized by condensation of 2,5-furandicarboxaldehyde with two equivalents of 4-fluoroaniline. The molecular structure consists of a central furan ring symmetrically bound to nearly coplanar iminomethyl groups with N-bonded 4-fluorophenyl rings that are significantly tipped out of the plane of the furan ring. In the crystal structure, the furan ring lies on a twofold rotation axis in space group C2/c with the furan ring and imine groups of adjacent molecules participating in C—H...N interactions to give furan-ring-centered hydrogen-bonded chains extending along [010]. Further cohesion of the crystal structure is achieved by participation of the peripheral 4-fluorophenyl rings in C—H...F hydrogen bonding and edge-to-face C—H...π interactions, resulting in a tri-periodic network. The resulting supramolecular chains formed by C—H...F hydrogen bonding extend in a direction parallel to [101]. |
| format | Article |
| id | doaj-art-8d87e5c61bbe4cd4a600c33f35d69dba |
| institution | Matheson Library |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-8d87e5c61bbe4cd4a600c33f35d69dba2025-07-07T07:54:06ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-07-0181762362610.1107/S2056989025005006wm5760Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furanMoira K. Lauer0Gary J. Balaich1Scott T. Iacono2Nathan J. Weeks3Department of Chemistry and Physics, University of North Carolina at Pembroke, Pembroke, NC 28372, USADepartment of Chemistry & Chemistry Research Center, USAF Academy, Colorado, Springs, CO 80840, USADepartment of Chemistry & Chemistry Research Center, USAF Academy, Colorado, Springs, CO 80840, USADepartment of Chemistry & Chemistry Research Center, USAF Academy, Colorado, Springs, CO 80840, USAThe title furan bis(imine) compound, 2,5-bis[(4-fluorophenyl)iminomethyl]furan, C18H12F2N2O, was synthesized by condensation of 2,5-furandicarboxaldehyde with two equivalents of 4-fluoroaniline. The molecular structure consists of a central furan ring symmetrically bound to nearly coplanar iminomethyl groups with N-bonded 4-fluorophenyl rings that are significantly tipped out of the plane of the furan ring. In the crystal structure, the furan ring lies on a twofold rotation axis in space group C2/c with the furan ring and imine groups of adjacent molecules participating in C—H...N interactions to give furan-ring-centered hydrogen-bonded chains extending along [010]. Further cohesion of the crystal structure is achieved by participation of the peripheral 4-fluorophenyl rings in C—H...F hydrogen bonding and edge-to-face C—H...π interactions, resulting in a tri-periodic network. The resulting supramolecular chains formed by C—H...F hydrogen bonding extend in a direction parallel to [101].https://journals.iucr.org/paper?S2056989025005006crystal structurefuranmonomergreen chemistry |
| spellingShingle | Moira K. Lauer Gary J. Balaich Scott T. Iacono Nathan J. Weeks Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan Acta Crystallographica Section E: Crystallographic Communications crystal structure furan monomer green chemistry |
| title | Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan |
| title_full | Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan |
| title_fullStr | Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan |
| title_full_unstemmed | Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan |
| title_short | Molecular and crystal structure of 2,5-bis[(4-fluorophenyl)iminomethyl]furan |
| title_sort | molecular and crystal structure of 2 5 bis 4 fluorophenyl iminomethyl furan |
| topic | crystal structure furan monomer green chemistry |
| url | https://journals.iucr.org/paper?S2056989025005006 |
| work_keys_str_mv | AT moiraklauer molecularandcrystalstructureof25bis4fluorophenyliminomethylfuran AT garyjbalaich molecularandcrystalstructureof25bis4fluorophenyliminomethylfuran AT scotttiacono molecularandcrystalstructureof25bis4fluorophenyliminomethylfuran AT nathanjweeks molecularandcrystalstructureof25bis4fluorophenyliminomethylfuran |