An X-Ray Crystallographic Study of Five Compounds from a Series of 1,x-bis-(4-Oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes

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• 作者：Valerio Bertolasi (2)
  Naomi J. Hunter (1)
  Keith Vaughan (1) keith.vaughan@smu.ca
• 关键词：X ; ray – Benzotriazinone – Alkane – Anthranilamide – Structural parameters
• 刊名：Journal of Chemical Crystallography
• 出版年：2011
• 出版时间：August 2011
• 年：2011
• 卷：41
• 期：8
• 页码：1105-1113
• 全文大小：368.3 KB
• 参考文献：1. Neunhofer H, Wiley PF (1978) In “Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines.” Vol. 33 in the series “HeterocyclicCompounds” ed. By Weissberger, A. and Taylor, E.C., publ. by John Wiley and Sons, New York, p 17
  2. Hunter N, Vaughan KJ (2006) Heterocycl Chem 43:731
  3. Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AGG, Polidori G, Spagna R (1999) J Appl Crystallogr 32:115
  4. Sheldrick GM SHELX-97 (1997) Program for crystal structure refinement, University of Gottingen, Germany
  5. Nardelli M (1995) J Appl Crystallogr 28:659
  6. Farrugia L (1999) J Appl Crystallogr 32:837
  7. Burnett MN, Johnson CK (1996) ORTEP III, Report ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN
  8. Rohrbaugh WJ, Meyers EK, Jacobson RA (1976) J Agric Food Chem 24:713
  9. Hunt WE, Schwalbe CH, Vaughan K (1983) Acta Crystallogr Sect C 39:738
  10. Hjortas J (1973) Acta Crystallogr Sect B 29:1916
  11. Li H, Jiang X, Ya Y, Fan C, Romoff T, Goodman M (1999) Org Lett 1:91
  12. Fernandez-Fomer D, Eritja R, Bardella F, Ruiz-Perez C, Solans X, Girait E, Pedroso E (1991) Tetrahedron 47:8917
  13. Baughman RG, Allen JL (1995) Acta Crystallogr Sect C 51:521
  14. Steiner T (2002) Angew Chem Int Ed 41:48
  15. Nishio M (2004) Cryst Eng Comm 6:130
• 作者单位：1. Department of Chemistry, Saint Mary’s University, Halifax, NS B3H 3C3, Canada2. Dipartimento di Chimica and Centro di Strutturistica Diffrattometrica, Universita-di Ferrara, Via L. Borsari, 46, 44100 Ferrara, Italy
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Organometallic Chemistry
  Crystallography
  Physical Chemistry
  Inorganic Chemistry
  
• 出版者：Springer Netherlands
• ISSN：1572-8854

文摘

Abstract The crystal structures of a series of bis-(4-oxo-3,4-dihydro-1,2,3-benzotriazin-3-yl)alkanes, compounds 5 to 9, have been determined by single crystal X-ray diffraction analysis. The structural parameters of the triazinone rings in the five compounds do not display systematic differences with respect to those reported for a few analogous compounds. The benzotriazinone rings in 5 and 9 are almost perpendicular to the alkylic chain. The molecules in the crystal packing are linked by means of a weak C–H···X H-bond (X = N/O). Compound 6 has two independent molecules in the asymmetric unit; one of the molecules displays disorder within the benzotriazinone moiety linked in position 1 to the propane alkylic group. The disordered molecule displays two conformations of the benzotriazinone linked in position 1 to the propane bridge. Compound 8 also displays disorder within the benzotriazinone moiety linked in position 1 to the pentane alkylic spacer group. The molecules of compound 7, in the crystal packing, also form intra and inter-molecular C–H···X (X = N/O) hydrogen bonds. None of these compounds show any tendency to adopt a folded conformation with intramolecular π–π stacking between benzotriazinone units. Crystal data: 5 C₁₆H₁₂N₆O_2, monoclinic, space group P2 ₁ /c, a = 4.8370(2)?, b = 14.7845(7)?, c = 10.0837(4)?, β = 95.430(2)°, V = 717.88(6)?3, for Ζ = 2; 6 C₁₇H₁₄N₆O_2, triclinic, space group P-1, a = 7.4237(4)?, b = 14.4738(9)?, c = 15.0359(10)?, α = 91.871(3)°, β = 92.147(3)°, γ = 101.233(3)°, V = 1582.2(2)?3, for Ζ = 4; 7 C₁₈H₁₆N₆O_2, monoclinic, space group C2/c, a = 33.8886(10)?, b = 6.4593(2)?, c = 16.0608(6)?, β = 102.298(1)°, V = 3435.0(2)?3, for Ζ = 8; 8 C₁₉H₁₈N₆O_2, triclinic, space group P-1, a = 7.2592(2)?, b = 7.6795(2)?, c = 16.1003(5)?, α = 85.292(1)°, β = 81.367(1)°, γ = 88.377(1)°, V = 884.26(4)?3, for Ζ = 2; 9 C₂₀H₂₀N₆O_2, monoclinic, space group P2 ₁ /c, a = 7.2668(2)?, b = 4.5612(1)?, c = 28.1993(12)?, β = 97.313(2)°, V = 927.07(5)?3, for Ζ = 2.