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Structural Investigations of Novel Indoloacridines

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Abstract

5,6-Dihydro-9-chloro-7-phenylindolo[3,2-c]acridinium sulfates (3a-c) were formed from 2,3,4,9-tetrahydro-1H-carbazol-1-ones (1a-c) on reaction with 2-amino-5-chlorobenzophenone. 3b and 3c are isostructural and all three sulfates crystallize in the triclinic system with the space group P\( \bar{1} \) each with two crystallographically independent organic cations and one sulfate anion in the asymmetric unit. 3a exhibits the parameters a = 9.8896(17), b = 14.165(2) and c = 14.583(2) Å, α = 83.184(3)°, β = 78.985(3)° and γ = 75.903(3)°; 3b a = 10.5713(9), b = 14.5667(12) and c = 14.9947(13) Å, α = 90.916(1)°, β = 97.153(1)° and γ = 97.208(1)°; and 3c a = 10.5505(10), b = 14.6090(13) and c = 15.2960(14) Å, and α = 91.4310(10)°, β = 98.8630(10)° and γ = 98.9100(10)°. The structure of 3c exhibits voids of 286 Å3 of ill defined and disordered solvate molecules. The structure of 3a is both non-merohedrally twinned and also exhibits an interesting type of pseudosymmetry. All but the sulfate ion and the ethylene moieties also fit with a unit cell half the size with only one independent cation, and disordered ethylene moieties and sulfate anions. The choice of unit cell was made based on the diffraction pattern and the absence of disorder in the larger cell, pointing towards alternating ordered ethylene and sulfate units rather than randomly disordered ones.

Index Abstract

[The structures of three indoloacridines 3a, 3b, and 3c with similar packing motifs are described. The structure of 3a is both non-merohedrally twinned and also exhibits an interesting type of pseudosymmetry by being a double volume ordered supercell of an alternative cell with disordered ethylene and sulfate anion moieties.]

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Acknowledgements

We acknowledge UGC, New Delhi, India, for the award of Major Research Project Grant No.F.No.31-122/2005. M.S thanks UGC, New Delhi for the award of research fellowship. Our sincere thanks to the Director, ISO Quality Assurance Cell, IICT, Hyderabad and, The Chairman, NMR Research Center, IISc, Bangalore for providing Mass and NMR spectra respectively. The authors would also like to thank Dr. Michael Ruf and Susan Byram of Bruker AXS for providing a copy of twinabs version 2007/3 prior to its official release. The X-ray diffractometer was funded by NSF Grant 0087210, Ohio Board of Regents Grant CAP-491, and by Youngstown State University.

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Authors and Affiliations

  1. Department of Chemistry, Bharathiar University, Coimbatore, 641-046, India

    Makuteswaran Sridharan & Karnam Jayarampillai Rajendra Prasad

  2. Department of Chemistry, Youngstown State University, One University Plaza, Youngstown, OH, 44555-3663, USA

    Aimable Ngendahimana & Matthias Zeller

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  1. Makuteswaran Sridharan
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  2. Karnam Jayarampillai Rajendra Prasad
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  3. Aimable Ngendahimana
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  4. Matthias Zeller
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Correspondence to Matthias Zeller.

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Sridharan, M., Prasad, K.J.R., Ngendahimana, A. et al. Structural Investigations of Novel Indoloacridines. J Chem Crystallogr 39, 270–278 (2009). https://doi.org/10.1007/s10870-008-9469-9

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  • DOI: https://doi.org/10.1007/s10870-008-9469-9

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