Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate
Abstract
The title compound, C39H30O6 center dot CDCl3, has a chemical threefold axis and an approximately planar structure, with an ethoxycarbonyl substituent on each of the terminal benzenes oriented in the same direction, thus forming a propellershaped molecule. This molecule is of particular interest in the field of metal-organic frameworks (MOFs), where its hydrolyzed analogue forms MOF structures with high surface areas. The benzene ring which occupies the centre of the molecule forms pi-pi interactions to the equivalent benzene ring at a perpendicular distance of 3.32 (1) angstrom. Centrosymmetric dimers formed in this way are interconnected by intermolecular C-H center dot center dot center dot pi interactions with a rather short H center dot center dot center dot CgA distance of 2.51 angstrom (CgA is the centroid of the central benzene ring). The molecules are arranged in regular parallel sheets. Within a sheet, molecules are interconnected via C-H center dot center dot center dot O in...teractions where all carbonyl O atoms participate in weak hydrogen bonds as hydrogen-bond acceptors. Neighbouring sheets are connected through the above-mentioned pi-pi and interactions.
Keywords:
crystal structure / metal-organic frameworks / MOFs / benzenetriyl triester / propeller-shaped molecule / monomolecular sheetsSource:
Acta Crystallographica Section C: Structural Chemistry, 2014, 70, 937-U43Funding / projects:
- Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds (RS-MESTD-Basic Research (BR or ON)-172014)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
DOI: 10.1107/S2053229614019147
ISSN: 0108-2701; 1600-5759
PubMed: 25279591
WoS: 000342905500003
Scopus: 2-s2.0-84925884781
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VinčaTY - JOUR AU - Knežević, Nikola AU - Novaković, Slađana B. AU - Bogdanović, Goran A. PY - 2014 UR - https://vinar.vin.bg.ac.rs/handle/123456789/149 AB - The title compound, C39H30O6 center dot CDCl3, has a chemical threefold axis and an approximately planar structure, with an ethoxycarbonyl substituent on each of the terminal benzenes oriented in the same direction, thus forming a propellershaped molecule. This molecule is of particular interest in the field of metal-organic frameworks (MOFs), where its hydrolyzed analogue forms MOF structures with high surface areas. The benzene ring which occupies the centre of the molecule forms pi-pi interactions to the equivalent benzene ring at a perpendicular distance of 3.32 (1) angstrom. Centrosymmetric dimers formed in this way are interconnected by intermolecular C-H center dot center dot center dot pi interactions with a rather short H center dot center dot center dot CgA distance of 2.51 angstrom (CgA is the centroid of the central benzene ring). The molecules are arranged in regular parallel sheets. Within a sheet, molecules are interconnected via C-H center dot center dot center dot O interactions where all carbonyl O atoms participate in weak hydrogen bonds as hydrogen-bond acceptors. Neighbouring sheets are connected through the above-mentioned pi-pi and interactions. T2 - Acta Crystallographica Section C: Structural Chemistry T1 - Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate VL - 70 SP - 937 EP - U43 DO - 10.1107/S2053229614019147 ER -
@article{ author = "Knežević, Nikola and Novaković, Slađana B. and Bogdanović, Goran A.", year = "2014", abstract = "The title compound, C39H30O6 center dot CDCl3, has a chemical threefold axis and an approximately planar structure, with an ethoxycarbonyl substituent on each of the terminal benzenes oriented in the same direction, thus forming a propellershaped molecule. This molecule is of particular interest in the field of metal-organic frameworks (MOFs), where its hydrolyzed analogue forms MOF structures with high surface areas. The benzene ring which occupies the centre of the molecule forms pi-pi interactions to the equivalent benzene ring at a perpendicular distance of 3.32 (1) angstrom. Centrosymmetric dimers formed in this way are interconnected by intermolecular C-H center dot center dot center dot pi interactions with a rather short H center dot center dot center dot CgA distance of 2.51 angstrom (CgA is the centroid of the central benzene ring). The molecules are arranged in regular parallel sheets. Within a sheet, molecules are interconnected via C-H center dot center dot center dot O interactions where all carbonyl O atoms participate in weak hydrogen bonds as hydrogen-bond acceptors. Neighbouring sheets are connected through the above-mentioned pi-pi and interactions.", journal = "Acta Crystallographica Section C: Structural Chemistry", title = "Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate", volume = "70", pages = "937-U43", doi = "10.1107/S2053229614019147" }
Knežević, N., Novaković, S. B.,& Bogdanović, G. A.. (2014). Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate. in Acta Crystallographica Section C: Structural Chemistry, 70, 937-U43. https://doi.org/10.1107/S2053229614019147
Knežević N, Novaković SB, Bogdanović GA. Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate. in Acta Crystallographica Section C: Structural Chemistry. 2014;70:937-U43. doi:10.1107/S2053229614019147 .
Knežević, Nikola, Novaković, Slađana B., Bogdanović, Goran A., "Monomolecular sheets of propeller-shaped triethyl 4,4 ,4 -[benzene-1,3,5-triyltris(ethyne-2,1-diyl)]tribenzoate deuterochloroform monosolvate" in Acta Crystallographica Section C: Structural Chemistry, 70 (2014):937-U43, https://doi.org/10.1107/S2053229614019147 . .