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Unusual hydrogen bond patterns contributing to supramolecular assembly: conformational study, Hirshfeld surface analysis and density functional calculations of a new steroid derivative.

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Title: Unusual hydrogen bond patterns contributing to supramolecular assembly: conformational study, Hirshfeld surface analysis and density functional calculations of a new steroid derivative.
Authors: Ruiz, Alberto1, Pérez, Hiram2 hperez@fq.uh.cu, Morera-Boado, Cercis3, Almagro, Luis1, da Silva, Cecilia C. P.4, Ellena, Javier4, García de la Vega, José M.5, Martínez-Álvarez, Roberto6, Suárez, Margarita1, Martín, Nazario6 nazmar@quim.ucm.es
Source: CrystEngComm. 2014, Vol. 16 Issue 33, p7802-7814. 13p.
Subjects: Hydrogen bonding, Supramolecular chemistry, Conformational analysis, Density functional theory, Chemical research
Abstract: A structural and conformational study of 3β-acetoxy-17-chloro-16-formyl-5α-androstan-16-ene has been carried out by using X-ray analysis and M06-2X density functional calculations. The compound crystallizes with three independent molecules in the asymmetric unit. Natural Bond Order and Atoms in Molecules methods were used for a better understanding of the key factors that determine the stability of this steroidal molecule, particularly the role of C-H...Cl intramolecular interactions. A detailed investigation of C-H...Cl and C-H...O intermolecular interactions, in addition to the most important van der Waals contribution, are presented by means of Hirshfeld surface analysis. The crystal packing exhibits an unusual intra- and intermolecular hydrogen bond pattern, and shows the importance of non-classical interactions in the construction of the supramolecular assembly. Excellent agreement between the theoretical and experimental data is found. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
Description
Abstract:A structural and conformational study of 3β-acetoxy-17-chloro-16-formyl-5α-androstan-16-ene has been carried out by using X-ray analysis and M06-2X density functional calculations. The compound crystallizes with three independent molecules in the asymmetric unit. Natural Bond Order and Atoms in Molecules methods were used for a better understanding of the key factors that determine the stability of this steroidal molecule, particularly the role of C-H...Cl intramolecular interactions. A detailed investigation of C-H...Cl and C-H...O intermolecular interactions, in addition to the most important van der Waals contribution, are presented by means of Hirshfeld surface analysis. The crystal packing exhibits an unusual intra- and intermolecular hydrogen bond pattern, and shows the importance of non-classical interactions in the construction of the supramolecular assembly. Excellent agreement between the theoretical and experimental data is found. [ABSTRACT FROM AUTHOR]
ISSN:14668033
DOI:10.1039/c4ce00709c