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C–H...O, C–H...π and π–π stacking interactions in 3-(2,4-dimethylphenyloxymethyl)-3,4-dihydroisocoumarin

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Abstract

3-(2,4-Dimethylphenyloxymethyl)-3,4-dihydroisocoumarin (C18H18O3) was prepared by the alkylation of o-lithio N-methyl benzamide with 2-(2,4-dimethylphenoxy)methyl oxirane, followed by alkaline hydrolysis. The compound crystallizes in the orthorhombic space group Pbca with unit cell parameters : a = 8.239(2) Å, b = 14.918(5) Å, c = 24.831(9) Å, Z = 8. The crystal structure was solved by direct methods and refined to R = 0.0514 for 1564 observed reflections. The heterocyclic ring adopts a distorted half-chair conformation. Molecules are connected by π–π interactions between phenyl rings of the isocoumarin nucleus forming dimers. Dimers are connected via C–H...O hydrogen bonds forming chains. Further intermolecular C–H...π hydrogen bonds link the dimer chains to form supramolecular structure.

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Acknowledgments

The authors are grateful to the Head, SAIF, IIT, Madras, Chennai, for the use of the intensity data collection facility. V.K.G. is grateful to the University Grants Commission, Govt. of India, for research funding under DRS Program [Project No. F-530/1/DRS/2001(SAP-I)].

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Authors and Affiliations

  1. Department of Physics, University of Jammu, Jammu Tawi, 180 006, India

    Sanjeev Goswami & Vivek K. Gupta

  2. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388 120, India

    D. I. Brahmbhatt & U. R. Pandya

Authors
  1. Sanjeev Goswami
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  2. Vivek K. Gupta
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  3. D. I. Brahmbhatt
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  4. U. R. Pandya
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Correspondence to Vivek K. Gupta.

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CCDC-248997 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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Goswami, S., Gupta, V.K., Brahmbhatt, D.I. et al. C–H...O, C–H...π and π–π stacking interactions in 3-(2,4-dimethylphenyloxymethyl)-3,4-dihydroisocoumarin. J Chem Crystallogr 37, 213–217 (2007). https://doi.org/10.1007/s10870-006-9173-6

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  • DOI: https://doi.org/10.1007/s10870-006-9173-6

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