Abstract
The molecular and crystal structures of spiro[1,3-indanedione-2,3′-(2′-phenyl)-1-azirine] (C16H9NO2) were determined by x-ray diffraction analysis. The crystals are monoclinic with a=6.987(1), b=13.987(3), c=12.418(1) Å, β=101.38(1)°, Z=4, dcalc=1.38 g · cm−3, and space group P21/a. The structure was decoded from 970 reflections, the intensities of which were measured with a P21 automatic diffractometer and refined by the method of least squares within the total matrix anisotropic approximation to R=0.069. The indanedione (A) and phenyl (C) rings are planar. The angle between the average (A) and azirine (B) planes is 91.8°, as compared with 85.65° between the A and C planes and 175.57° between the B and C planes. The bond lengths in the A and C rings have their usual values. The C2-N bond (1.57 Å) in the B ring is lengthened considerably. The packing of the molecules in the crystal is accomplished at the van der Waals distances. An explanation of the practically observed chemical behavior of the compound is proposed on the basis of the geometrical characteristics of the molecule.
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L. S.Geita,I. É. Dal'berga, and A. K.Grinvalde, Izv. Akad. Nauk Latv. SSR, Ser. Khim., 494 (1974).
L. S. Geita, I. É. Dalberga, A. K. Grinvalde, and I. S. Yankovska, Khim. Geterotsikl. Soedin., No. 1, 65 (1976).
A. Hassner and F. Fowler, J. Am. Chem. Soc., 90, 2896 (1968).
J. Music and F. Matsen, J. Am. Chem. Soc., 72, 5256 (1950).
G. Collet and G. Leroy, J. Chim. Phys. Phys.-Chim. Biol., 71, 1033 (1974).
G. Germain, P. Main, and M. M. Woolfson, Acta Cryst., A27, 368 (1971).
G. Bravic, F. Bechtel, J. Gaultier, and C. Hauw, Cryst. Struct. Comm., 5, No. 1, 1 (1976).
F. Bechtel, G. Bravic, J. Gaultier, and C. Hauw, Cryst. Struct. Comm., 1, No. 3, 159 (1972).
A. E. Shvets, Ya. Ya. Bleidelis, R. P. Shibaeva, and L. O. Atovmyan, Zh. Strukt. Khim., 13, 745 (1972).
A. E. Shvets, A. A. Kemme, Ya. Ya. Bleidelis, Ya. F. Freimanis, and R. P. Shibaeva, Zh. Strukt. Khim., 14, 576 (1973).
E. G. Cox, D. W. J. Cruickshank, and J. A. S. Smith, Proc. Roy. Soc., A247, 1 (1958).
O. Bastiansen, F. N. Fritsch, and K. Hedberg, Acta Cryst., 17, 538 (1964).
S. A. Giller, Ya. Ya. Bleidelis, A. A. Kemme, A. V. Eremeev, and V. A. Kholodnikov, Zh. Strukt. Khim., 16, 411 (1975).
J. Galloy, J. P. Putzeys, G. Germain, J. P. Declercq, and M. Van Meersche, Acta Cryst., B30, 2462 (1974).
R. Macanlay, L. Burnelle, and C. Sandafy, Theor. Chim. Acta, 29, 1 (1973).
A. Walsh, Trans. Faraday Soc., 45, 179 (1949).
G. Closs and H. Klinger, J. Am. Chem. Soc., 87, 3265 (1965).
N. Cromwell and M. Graff, J. Org. Chem., 17, 414 (1952).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1217–1220, September, 1977.
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Mishnev, A.F., Bleidelis, Y.Y. & Geita, L.S. Molecular and crystal structures of spiro[1,3-indanedione-2,3′-(2′-phenyl)-1′-azirine] and its chemical properties. Chem Heterocycl Compd 13, 982–985 (1977). https://doi.org/10.1007/BF00472452
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DOI: https://doi.org/10.1007/BF00472452