Abstract
This is the first work to synthesize 4,4,10,10-tetramethyl-1,3,7,9-tetraazospiro[5.5]undecane-2,8-dione monohydrate, monochloride, mononitrate, and teteraiodotellurate: C11H20N4O2·H2O (I), C11H21N4O +2 ·Cl− (II), C11H21N4O +2 ·NO −3 (III), and 2(C11H21N4O +2 )·TeI 2−4 ·C3H6O (IV) and determine their structures. Crystals of I are monoclinic: space group P21/c, at 298 K a = 5.7118(7) Å, b = 17.842(2) Å, and c = 13.5905(16) Å; β = 91.621(11)°; V = 1384.5(3) Å3; d x = 1.239 g/cm3, Z = 4. Crystals of II are tetragonal: space group P43, at 298 K a = 6.4134(3) Å and c = 34.292(2) Å; V = 1410.47(14) Å3; d x = 1.303 g/cm3; Z = 4. Crystals of III are triclinic: space group \(P\bar 1\), at 298 K a = 8.7614(14) Å, b = 9.3904(18) Å, and c = 10.028(2) Å; α = 63.27(2)°, β = 78.591(16)°, and γ = 84.308(15)°; V = 722.3(2) Å3; d x = 1.40 g/cm3; Z = 2. Crystals of IV are triclinic: space group \(P\bar 1\), at 100 K a = 10.4630(4) Å, b = 11.9372(6) Å, and c = 16.4118(5) Å; α = 72.058(3)°, β = 76.406(3)°, and γ = 87.029(3)°; V = 1895.04(12) Å3; d x = 2.06 g/cm3; Z = 2. The synthesis of s and p metals with spirocarbone in acetone medium is found to be impossible due to the protonation by the oxygen atom of the carbonyl group. The main crystalline product of the complexation reaction is a monosalt. Evidence is provided that the recrystallization and drying of the synthesized spirocarbone preparation yields monohydrate (I); its purity and monophasity is confirmed by a Rietveld refinement of the powder X-ray pattern. The lattice parameters at room temperature are: a = 5.6885(12) Å, b = 17.8496(12) Å, and c = 13.518(3) Å; β = 91.449(15)°; V = 1372.1(4) Å3. The sample is monophasic.
Similar content being viewed by others
References
A. Weinschenk, Chem. Ber., 34, No. 2, 2186 (1901).
G. Zigeuner, E. Fuchs, H. Brunnetti, et al., Monatsh. Chem., 97, No. 1, 36 (1966).
R. L. Lipnick and J. D. Fissekis, J. Org. Chem., 44, No. 26, 4867 (1979).
V. P. Mamaev and V. F. Sedova, Khimiya Geterots. Soed., 3, No. 3, 571 (1967).
H. H. Hatt, G. D. Liohtenwalter, and G. H. Riesser, Aust. J. Chem., 23, 561 (1970).
A. R. Butler and I. Hussain, J. Chem. Soc., Perkin Trans., 2, 229 (1980).
A. R. Butler and I. Hussain, J. Chem. Soc., Perkin Trans., 2, 232 (1980).
V. F. Sedova and V. M. Mamaev, Khimiya Geterots. Soed., 4, No. 5, 921 (1968).
H. H. Hatt and A. K. Triffett, Chem. Commun., 19, 439 (1965).
A. F. Fedorenko, Relative Solubility Method: Theory and Practice, Dr. Sci. (Chem.) Dissertation, Kiev: Institute of General and Inorganic Chemistry (1992).
M. Kaftory, M. Kapon, and M. Botoshansky, Chem. Mater., 6, 1245 (1994).
A. Mahbub, H. Fazal, and L. Khalid, Ind. J. Exp. Biology, 30, 1181 (1992).
K. P. Dudok, A. M. Fedorovich, T. G. Dudok, et al., Studia Biologica [in Ukrainian], 3, No. 2, 23 (2009).
L. S. Starikovich, M. A. Starikovich, O. N. Rechitskii, et al., Studia Biologica [in Ukrainian], 3, No. 2, 93 (2009).
K. P. Dudok, L. S. Starikovich, O. N. Rechitskii et al., Visn. Lviv. Univ. Ser. Biolog., 60, 126 (2012).
A. G. Musatov, A. A. Semyashkina, and R. F. Dashevskii, Zh. Khranenie i Pererabotka Zerna [in Ukrainian], No. 7, 38 (2007).
A. I. Zlobin, Morphophysiological and Biochemical Changes in Barley Plants in Response to Growth Regulator Treatment, Extended Abstract of Cand. Sci. (Biol.) Dissertation, Moscow: K.A. Timiryazev Moscow Agricultural Academy (1994).
A. S. Gurevich, V. A. Titov, E. V. Babaeva, et al., Introduction, Acclimatization, and Cultivation of Plants [in Russian], Kaliningrad Univ., Kaliningrad (1998), p. 50.
L. I. Khrustaleva, Exogenous Growth Regulators and Their Effect on the Plant Genome, Extended Abstract of Dr. Sci. (Biol.) Dissertation, Moscow: K.A. Timiryazev Moscow Agricultural Academy (1994).
M. V. Kozichar, Methods of Enhancement of Wool Productivity of Askania Fine-Wool Sheep [in Ukrainian]. Biological Sciences Candidate’s Dissertation, Kherson, KhNTU (1999).
E. E. Netreba, A. M. Fedorenko, and A. A. Pavlov, Zh. Nauk. Visn., Uzhgorod Univ., Ser. Khimiya, 25, No. 1, 107 (2011).
V. A. Klimova, Basic Micromethods for Organic Compound Analysis [in Russian], Khimiya, Moscow (1975).
G. Sheldrick, Acta Crystallogr. A, 64, 112 (2008).
J. Rodriguez-Carvajal and T. Roisnel, FullProf.98 and WinPLOTR: New Windows 95/NT Applications for Diffraction. Commission for Powder Diffraction, International Union of Crystallography.-Newsletter No. 20 (May–August) Summer, 1998.
V. Gutmann, Coordination Chemistry in Non-Aqueous Solutions, Springer-Verlag, New York (1968).
Yu. Ya. Fialkov, Not Only in Water [in Russian], Khimiya, Leningrad (1989).
Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 58, No. 5, 713 (1989).
H.-B. Burgi and J. D. Dunitz, Structure Correlation, Vol. 2, VCH, Weinheim (1994).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2014 E. E. Netreba, E. S. Papayanina.
__________
Translated from Zhurnal Strukturnoi Khimii, Vol. 55, No. 4, pp. 756–764, July–August, 2014.
Rights and permissions
About this article
Cite this article
Netreba, E.E., Papayanina, E.S. Study of new molecular and crystal structures of 4,4,10,10-tetramethyl-1,3,7,9-tetraazospiro[5.5]undecane-2,8-dione and its salts: Monochloride, mononitrate, and tetraiodotellurate. J Struct Chem 55, 722–730 (2014). https://doi.org/10.1134/S0022476614040209
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476614040209