Abstract
Crystal structures of a series of p-halogenated 6,6-diphenylfulvenes 2–5 are reported and comparatively discussed including the known structure of the non-halogenate parent compound 1. The molecular structures show twisted conformations of the plane aryl and fulvene subunits against each other, rather unaffected by the different halogen substituents. The packing structures exclusively involve C–H···X (X = F, Cl, π) contacts while Hal···Hal and π-stacking interactions do not occur.
Similar content being viewed by others
References
Bergmann ED (1968) Chem Rev 68:41
Hafner K, Häfner KH, König C, Kreuder M, Ploss G, Schulz G, Sturm E, Vöpel KH (1963) Angew Chem 75:35
Behrens U (1976) J Organomet Chem 107:103
Edelmann F, Lubke B, Behrens U (1982) Chem Ber 115:1325
Christofides A, Howard JAK, Spencer JL, Stone FGA (1982) J Organomet Chem 232:279
Wadepohl H, Pritzkow H (1991) Acta Crystallogr C47:2061
Blake AJ, Dyson PJ, Johnson BFG, Pearsons S, Reed D, Shephard DS (1995) Organometallics 14:4199
Teuber R, Köppe R, Linti G, Tacke M (1997) J Organomet Chem 545–546:105
Schwarzer A, Bombicz P, Weber E (2010) J Fluorine Chem 131:435
Martin JG, Hill RK (1961) Chem Rev 61:537
Bolte M, Amon M (1997) Acta Crystallogr C53:1354
Vittal J, Zaworotko M, Tiekink ERT (eds) (2010) Organic crystal engineering. Wiley, New York
Aakeröy CB, Champness NR, Janiak C (2010) CrystEngComm 12:22
Leonard J, Lygo B, Procter G (1996) Praxis der Organischen Chemie. VCH, Weinheim, pp 53–68
Bergmann E, Engel L, Meyer H (1932) Ber Dtsch Chem Ges 65:446
Thiele J (1900) Ber Dtsch Chem Ges 33:666
Alper H, Laycock DE (1981) Tetrahedron Lett 22:33
Scherer A, Kollak K, Lützen A, Friedemann M, Haase D, Saak W, Beckhaus R (2005) Eur J Inorg Chem 1003
Kresze G, Rau S, Sabelus G, Goetz H (1961) Liebigs Ann Chem 648:51
Takeno M (1970) Nippon Kagaku Zasshi 91:1182
Bruker (2004) SMART (Version 5.628) and SAINT (Version 6.45a). Bruker AXS Inc, Madison, WI, USA
Sheldrick GM (2008) Acta Crystallogr A64:112
Sheldrick GM (2004) SADABS: program for empirical absorption corrections. University of Göttingen, Germany
Spek AL (2009) Acta Crystallogr D65:148
Farrugia LJ (1997) J Appl Cryst 30:565
Dance I (2004) In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 1076–1092
Nishio M (2004) CrystEngComm 6:130
Thallapally PK, Nangia A (2001) CrystEngComm 3:114
Brammer L, Bruton EA, Sherwood P (2001) Cryst Growth Des 1:277
Awwadi FF, Willett RD, Peterson KA, Twamley B (2006) Chem Eur J 12:8952
Fourmigué M (2009) Curr Opin Solid State Mater Sci 13:36
Reddy CM, Kirchner MT, Gundakaram RC, Padmanabhau KA, Desiraju GR (2006) Chem Eur J 12:2222
Day GM, Price SL (2003) J Am Chem Soc 125:16434
Csöregh I, Brehmer T, Bombicz P, Weber E (2001) Cryst Eng 4:343
Hosseinzadeh R, Seichter W, Sanaeishoar T, Weber E (2007) Supramol Chem 19:353
Hauptvogel IM, Schwarzer A, Weber E (2007) Acta Crystallogr E 63:2106
Jetti RKR, Xue F, Mak TCW, Nangia A (2000) Cryst Eng 2:215
Nangia A, Desiraju GR (1998) In: Weber E (ed) Design of organic solids, topics in current chemistry, vol 198. Springer, Berlin-Heidelberg, pp 57–95
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Schwarzer, A., Seichter, W. & Weber, E. X-ray crystal structures of p-halogenated 6,6-diphenylfulvenes. Struct Chem 22, 95–101 (2011). https://doi.org/10.1007/s11224-010-9685-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-010-9685-8