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Structure determination from X-ray powder diffraction, DFT calculation, and Hirshfeld surface analysis of two fused bicyclic and tricyclic compounds

Published online by Cambridge University Press:  28 February 2017

Uday Das ,
Tanusri Dey ,
Paramita Chatterjee  and
Alok K. Mukherjee
Uday Das
Affiliation:
Department of Physics, Jadavpur University, Jadavpur, Kolkata-700032, India Department of Physics, Hooghly Mohsin College, Chinsurah, Hooghly-712101, India
Tanusri Dey
Affiliation:
Department of Physics, Jadavpur University, Jadavpur, Kolkata-700032, India
Paramita Chatterjee
Affiliation:
Department of Physics, Jadavpur University, Jadavpur, Kolkata-700032, India Department of Physics, Lady Brabourne College, Kolkata-700017, India
Alok K. Mukherjee*
Affiliation:
Department of Physics, Jadavpur University, Jadavpur, Kolkata-700032, India
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

Crystal structures of two fused cyclic systems have been determined from X-ray powder diffraction data and their molecular geometries and intermolecular interactions have been analyzed by solid state DFT calculation and Hirshfeld surface evaluation, respectively.

Crystal structures of two fused cyclic compounds, 4-(methyl(sulfonyl)methoxy-2-vinyl)-2S*,3aR*,4S*,5,7aS*-(hexahydro-1H-indan-3a-yl)methylmethanesulfonate (1) and (1S*,2S*,4S*,7R*)-7-(dimethyl(phenyl)silyl)-4′,5′-dihydro-2′H-spiro[bicyclo[2.2.1]hept[5]ene-2,3′-furan]-2′-one (2), have been solved from laboratory X-ray powder diffraction data using direct space approach and refined following the Rietveld method. In the absence of strong hydrogen bond donating groups, the crystal packing of 1 and 2 exhibits C–H ⋯ O hydrogen bonds and C–H ⋯ π interactions forming two-dimensional (2D) supramolecular network. The nature of intermolecular interactions in 1 and 2 has been analyzed through the Hirshfeld surface and 2D fingerprint plots. The density functional theory optimized molecular geometries in 1 and 2 agree closely with those obtained from the crystallographic study. Hirshfeld surface analysis of 1, 2 and a few related fused carbocyclic and carbooxacyclic systems retrieved from the Cambridge Structural Database indicates that about 85% of Hirshfeld surface area in these compounds are because of H ⋯ H and O ⋯ H interactions.

Keywords

X-ray powder diffractionstructure determinationfused cyclic systemHirshfeld surface analysisDFT calculation
Type
Technical Articles
Information
Powder Diffraction , Volume 32 , Issue 2 , June 2017 , pp. 86 - 92
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Copyright
Copyright © International Centre for Diffraction Data 2017 

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