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X-ray crystal structure analysis of nitroxazepine: 10-(3-dimethylaminopropyl)-2-nitro-10,11-dihydrodibenz [b,f][l,4]oxazepin-11-one

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Abstract

The title compound, C18H19O4N3,M r=341, the base (I) of the dibenzoxazepine anti-depressant drug Sintamil, crystallizes in the orthorhombic space group,Pbca withZ=8 in a cella=8.636(2),b=23.687(3),c=16.787(3)Å,V c=3434 Å3. The structure was solved by direct methods and refined toR=0.102 (R w=0.093) with 1348 observed CuKα reflections. The tricyclic framework takes up a saddle shape with the heterocyclic ring in boat conformation; the flanking planar aromatic rings make angles 148.2(3), 150.8(3)° with the central ring plane, compared with 143.5(5), 158.1(5)° in Sintamil monohydrate (II). BothI andII have extended-CNMe2 side chains (with appreciable thermal motion); this conformation, and the distances of the -N(CH3)3 nitrogen to the centers of aromatic rings (6.4 and 7.8 Å inI), are consistent with inhibition of uptake mechanisms underlying the pharmacological action.

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References

  • Drake J. A. G. and Jones D. W. (1977)J. Pharm. Pharmac. 29, 303.

    Google Scholar 

  • Drake, J. A. G., and Jones, D. W. (1982)Acta Crystallogr. B 38, 200.

    Google Scholar 

  • International Tables for X-ray Crystallography (1974) Vol. IV (Kynoch Press, Birmingham), pp. 99–102.

  • Main, P., Fiske, S. J., Hull, S. E., Lessinger, L., Germain, G., Declercq, J.-P., and Woolfson, M. M. (1980)A system of computer programs for the automatic solution of crystal structures from X-ray diffraction data. (Universities of York, England and Louvain, Belgium).

    Google Scholar 

  • Martin, A. R., Paradkar, V. M., Peng, G. W., Speth, R. C., Yamayura, H. I., and Horn, A. S. (1980).J. Med. Chem. 23, 865.

    PubMed  Google Scholar 

  • Nagarajan, K., David, J., Kaul, C. L., Mailer, R. K., Rao, R. R., and Grewal, R. S. (1975).Ind. J. Physiol. Pharmacol. 19, 39.

    Google Scholar 

  • Post, M. L., Kennard, O., and Horn, A. S. (1975)Acta Crystallogr. B 31, 1008.

    Google Scholar 

  • Sheldrick, G. M. (1978) An integrated system for solving, refining and displaying crystal structures from diffraction data. University of Göttingen, Germany.

    Google Scholar 

  • Usha, R., Bhadbhade, M. M., Venkatesan, K., Nagarajan, K., and David, J. (1982)Acta Crystallogr. B 38, 1854.

    Google Scholar 

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Author notes

  1. O. Johnson

    Present address: Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, Cambridge, UK

Authors and Affiliations

  1. Chemistry and Chemical Technology, University of Bradford, BD7 1DP, Bradford, West Yorkshire, UK

    O. Johnson & D. W. Jones

  2. Searle (India) Ltd., Thane-Benlapur Road, 400601, Thane, India

    K. Nagarajan

  3. Department of Organic Chemistry, Indian Institute of Science, 560012, Bangalore, India

    M. M. Bhadbhade & K. Venkatesan

Authors
  1. O. Johnson
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  2. D. W. Jones
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  3. K. Nagarajan
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  4. M. M. Bhadbhade
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  5. K. Venkatesan
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Johnson, O., Jones, D.W., Nagarajan, K. et al. X-ray crystal structure analysis of nitroxazepine: 10-(3-dimethylaminopropyl)-2-nitro-10,11-dihydrodibenz [b,f][l,4]oxazepin-11-one. Journal of Crystallographic and Spectroscopic Research 22, 579–583 (1992). https://doi.org/10.1007/BF01161343

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  • DOI: https://doi.org/10.1007/BF01161343

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