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Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies

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Abstract

Crystals of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane -1,3,5,9-tetraone were grown in polar solvents and subjected to single crystal X-ray diffraction. The molecular crystal is Triclinic, P-1, a= 8.3734 (19) Å, b= 12.382 (3) Å, c= 12.871 (3) Å, α= 66.639 (7) ∘, β= 85.148 (7) ∘, γ= 70.690 (6) ∘, V= 1154.5 (5)Å 3, Z= 2, D calc= 1.519 g cm −3. The optimized molecular structure of the studied compound using B3LYP/6-311G(d,p) method showed good agreement with the X-ray structure. The electronic and spectroscopic properties of the title compound were predicted. The NBO calculations were used to calculate the natural atomic charges at the different atomic sites as well as the intramolecular charge transfer (ICT) interactions among the most significant natural orbitals. The high LP(N) → BD*(2)C-O ICT interaction energies indicate strong electron delocalization from the lone pair of the N-atoms of the pyrimidinetrione ring to the adjacent carbonyl groups. In contrast, the small LP(O) →BD*(1)C-H stabilization energies (E (2)) indicated weak C-H—O interactions. Experimentally, the studied compound showed the most intense electronic transition band at 232 nm which is calculated using TD-DFT method as a shoulder at 231.3 nm (f =0.0832) and it belongs to H-3/H-1 →L+1 and H-2 →L+2 excitations. The GIAO calculated 1H and 13C NMR chemical shifts showed good correlations with the experimental data.

The X-Ray single crystal structure and DFT computation of the 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4-diazaspiro[5.5]undecane -1,3,5,9-tetraone are discussed.

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Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding this Research group NO (RG -044-1435-1436).

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Authors and Affiliations

  1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia

    MOHAMMAD SHAHIDUL ISLAM, ASSEM BARAKAT & ABDULLAH MOHAMMED AL-MAJID

  2. Department of Chemistry, Rabigh College of Science and Art, King Abdulaziz University, P. O. Box 344, Rabigh, 21911, Saudi Arabia

    SAIED M SOLIMAN

  3. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt

    ASSEM BARAKAT & SAIED M SOLIMAN

  4. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    HAZEM A GHABBOUR & HOONG-KUN FUN

  5. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt

    HAZEM A GHABBOUR

  6. X-Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang, 11800, Malaysia

    HOONG-KUN FUN

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  1. MOHAMMAD SHAHIDUL ISLAM
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  2. ASSEM BARAKAT
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  5. HAZEM A GHABBOUR
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Correspondence to ASSEM BARAKAT.

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Supplementary Information

All additional information pertaining to characterization of the target compound: The correlation graphs between calculated and observed geometrical parameters of the title compound are shown in figure S1 S1. NMR (figures S2 and S3), IR (figure S4), H-bonding information (table S1) and NMR chemical shift data (table S2) are given in the Supplementary Information which is available at www.ias.ac.in/chemsci.

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ISLAM, M.S., BARAKAT, A., AL-MAJID, A.M. et al. Crystal Structure of 7,11-bis(2,4-dichlorophenyl)-2,4-dimethyl-2,4- diazaspiro[5.5]undecane -1,3,5,9-tetraone and its computational studies. J Chem Sci 127, 2039–2050 (2015). https://doi.org/10.1007/s12039-015-0969-9

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