Crystal Structure of the 2:1 Charge-Transfer Salt Derived from Hexamethylenetetraselenafulvalene (HMTSF) and 7,7,8,8-Tetracyano-p-Quinodimethane (TCNQ), (HMTSF)₂(TCNQ)

References

• Melby , L. R. , Harder , R. J. , Hertler , W. R. , Mahler , W. , Benson , R. E. and Mochel , W. E. 1962 . J. Am. Chem. Soc. , 84 : 3374
   Web of Science ®Google Scholar
• Schegolev , I. F. 1972 . Phys. Stat. Solid: , 12 : 9
   Google Scholar
• Herbstein , F. H. 1971 . Perspectives in Structural Chemistry , Edited by: Dunitz , J. D. and Ibers , J. A. Vol IV , New York : John Wiley and Sons .
   Google Scholar
• Garito , A. F. and Heeger , A. J. 1974 . Acct. Chem. Res. , 7 : 232
   Web of Science ®Google Scholar
• Torrance , J. B. 1979 . Acct. Chem. Res. , 12 : 79
   Web of Science ®Google Scholar
• Bloch , A. N. Acct. Chem. Res. , in press
   Google Scholar
• Kistenmacher , T. J. 1978 . Ann. N. Y. Acad. Sci. , 313 : 333
   Google Scholar
• Ferraris , J. P. , Cowan , D. O. , Walatka , V. and Perlstein , J. 1973 . J. Am. Chem. Soc. , 95 : 948
   Web of Science ®Google Scholar
• Coleman , L. B. , Cohen , M. J. , Sandman , D. J. , Yamagishi , F. G. , Garito , A. F. and Heeger , A. J. 1973 . Solid State Commun. , 12 : 1125
   Web of Science ®Google Scholar
• Kistenmacher , T. J. , Phillips , T. E. and Cowan , D. O. 1974 . Acta Crystallogr. , B30 : 763
   Google Scholar
• Ferraris , J. P. , Poehler , T. O. , Bloch , A. N. and Cowan , D. O. 1973 . Tett. Lett. , : 2553
   Google Scholar
• Phillips , T. E. , Kistenmacher , T. J. , Bloch , A. N. , Ferraris , J. P. and Cowan , D. O. 1977 . Acta Crystallogr. , B33 : 422
   Google Scholar
• Bloch , A. N. , Carruthers , T. F. , Poehler , T. O. and Cowan , D. O. 1977 . Chemistry and Physics of One-Dimensional Metals , Edited by: Keller , H. J. 47 – 58 . New York : Plenum Press .
   Google Scholar
• Bechgaard , K. , Kistenmacher , T. J. , Bloch , A. N. and Cowan , D. O. 1977 . Acta Crystallogr. , B33 : 417
   Google Scholar
• Greene , R. L. , Mayerle , J. J. , Schumaker , R. R. , Castro , G. , Chaikin , P. M. , Etemad , S. and La Placa , S. J. 1976 . Solid State Commun. , 20 : 943
   Web of Science ®Google Scholar
• Chasseau , D. , Comberton , G. , Gaultier , J. and Hauw , C. 1978 . Acta Crystallogr. , B34 : 689
   Google Scholar
• Silverman , B. D. and La Placa , S. J. 1978 . J. Chem. Phys. , 69 : 2585
   Web of Science ®Google Scholar
• Bloch , A. N. , Cowan , D. O. , Bechgaard , K. , Pyle , R. E. and Banks , R. H. 1975 . Phys. Rev. Lett. , 34 : 1561
   Web of Science ®Google Scholar
• Phillips , T. E. , Kistenmacher , T. J. , Bloch , A. N. and Cowan , D. O. 1976 . J. Chem. Soc. Chem. Commun. , : 344
   Google Scholar
• Abbreviations mentioned in the text are: TCNQ (tetracyano-p-quinodimethane); TCNQF4 and 2.5-TCNQF2 (perfluoro-TCNQ and 2.5-difluoro-TCNQ); TNAP (tetracyano-3,7-naphthoquinodimethane); TTF (tetrathiafulvalene); TMTTF, HMTTF, DBTTF, DTTTF, and TETTF (tetramethyl-TTF; hexamethylene-TTF; dibenzo-TTF; dithieno-TTF; and, tetraethyl-TTF); HMTSF and TMTSF (hexamethylene- and tetramethyl-tetraselenafulvalene); NBP (5-(1-butyl)-phenazine)
   Google Scholar
• Torrance , J. B. , Mayerle , J. J. , Bechgaard , K. , Silverman , B. D. and Tomkiewicz , Y. 1980 . Phys. Rev. B. , 22 : 4960
   Web of Science ®Google Scholar
• Hawley , M. E. , Poehler , T. O. , Carruthers , T. F. , Bloch , A. N. , Cowan , D. O. and Kistenmacher , T. J. 1978 . Bull. Am. Phys. Soc. , 23 : 424
   Google Scholar
• Pyte , E. 1974 . Phys. Rev. B , 10 : 4637
   Google Scholar
• Jacobs , I. S. , Bray , J. W. , Hart , H. R. , Interrante , L. V. , Kasper , J. S. , Watkins , G. D. , Prober , D. E. and Bonner , J. C. 1976 . Phys. Rev. B. , 14 : 3036
   Web of Science ®Google Scholar
• Emge , T. J. , Wiygul , F. M. , Ferraris , J. P. and Kistenmacher , T. J. 1981 . Mol. Cryst. Liq. Cryst. , 78 : 295
   Web of Science ®Google Scholar
• Emge , T. J. , Bryden , W. A. , Wiygul , F. M. , Bloch , A. N. , Cowan , D. O. and Kistenmacher , T. J. J. Chem. Phys. , in press
   Google Scholar
• Shu , P. , Chiang , L. , Emge , T. , Holt , D. , Kistenmacher , T. , Lee , M. , Stokes , J. , Poehler , T. , Bloch , A. and Cowan , D. 1981 . J. Chem. Soc. Chem. Commun. , 920
   Google Scholar
• Bryden , W. A. , Emge , T. J. , Stokes , J. P. , Bloch , A. N. , Cowan , D. O. and Kistenmacher , T. J. to be published
   Google Scholar
• Soos , Z. G. 1974 . Ann. Rev. Phys. Chem. , 25 : 121
   Web of Science ®Google Scholar
• Strebel , P. J. and Soos , Z. G. 1970 . J. Chem. Phys. , 53 : 4077
   Web of Science ®Google Scholar
• Lyubovska , R. N. 1975 . Izv. Akad. Nauk SSSR Ser. Khim. , : 177
   Google Scholar
• Jones , M. T. , Kellerman , R. , Troup , A. and Sandman , D. J. Proc. Intl. Conf. on Low Dimensional Synthetic Metals . Denmark : Helsingor .
   Google Scholar
• Kistenmacher , T. J. , Emge , T. J. , Wiygul , F. M. , Bryden , W. A. , Chappell , J. S. , Stokes , J. P. , Chiang , L. Y. , Cowan , D. O. and Bloch , A. N. 1981 . Solid State Commun. , 39 : 415
   Web of Science ®Google Scholar
• Emge , T. J. , Wiygul , F. M. , Chappell , J. S. , Bloch , A. N. , Ferraris , J. P. , Cowan , D. O. and Kistenmacher , T. J. 1982 . Mol. Cryst. Liq. Cryst. , 87 : 137
   Web of Science ®Google Scholar
• Kistenmacher , T. J. , Emge , T. J. , Bloch , A. N. and Cowan , D. O. 1982 . Acta Crystallogr. , B38 : 1193
   Google Scholar
• Galinge , J. L. , Fabre , J. M. and Giral , L. 1977 . Acta Crystallogr. , B33 : 3827
   Google Scholar
• Harms , R. H. , Keller , H. J. , Nothe , D. , Wehe , D. , Heimer , N. , Metzger , R. M. , Gundel , D. and Sixl , H. 1982 . Mol. Cryst. Liq. Cryst. , 85 : 249
   Web of Science ®Google Scholar
• Bechgaard , K. , Cowan , D. O. , Bloch , A. N. and Henriksen , L. 1975 . J. Org. Chem. , 40 : 746 and references therein
   Web of Science ®Google Scholar
• Wilson , A. J. C. 1942 . Nature (London) , 150 : 151
   Google Scholar
• Hanson , H. P. , Herman , F. , Lea , J. D. and Skillman , S. 1964 . Acta Crystallogr. , 17 : 1040
   Web of Science ®Google Scholar
• Stewart , R. F. , Davidson , E. R. and Simpson , W. T. 1965 . J. Chem. Phys. , 42 : 3175
   Web of Science ®Google Scholar
• Cromer , D. T. and Liberman , D. 1970 . J. Chem. Phys. , 53 : 1891
   Web of Science ®Google Scholar
• Crystallographic programs used include Wehe, Busing and Levy's ORABS, Busing, Martin and Levy's ORFLS (modified), Zalkin's FORDAP, and Pippy and Ahmed's MEAN PLANE
   Google Scholar
• Johnson , C. K. 1965 . Oak Ridge, Tenn : Oak Ridge National Laboratory . ORTEP, Report ORNL-3794
   Google Scholar
• Kistenmacher , T. J. , Rossi , M. , Cowan , D. O. and Bloch , A. N. to be published
   Google Scholar
• Pauling , L. 1960 . The Nature of the Chemical Bond. , 3rd. Ed. , Ithaca : Cornell University Press . Van der Waals radii employed include the following: Se (2.0 Å); C (1.75 Å); N (1.5 Å). Values taken from
   Google Scholar
• Thorup , N. , Rindorf , G. , Soling , H. and Bechgaard , K. 1981 . Acta Crystallogr. , B37 : 1236
   Google Scholar
• Wudl , F. 1981 . J. Am. Chem. Soc. , 103 : 7064
   Web of Science ®Google Scholar
• Bechgaard , K. , Caneiro , K. , Rasmussen , F. B. , Olsen , M. , Rindorf , G. , Jacobsen , C. S. , Pederson , H. J. and Scott , J. C. 1981 . J. Am. Chem. Soc. , 103 : 2442
   Web of Science ®Google Scholar
• Murata , K. , Anzai , H. , Saito , G. , Kajimura , K. and Ishiguro , T. 1981 . J. Phys. Soc. (Japan) , 50 : 3529
   Google Scholar
• McConnell , H. M. , Hoffman , B. M. and Metzger , R. M. 1965 . Proc. Natl. Acad. Sci. , 53 : 46
   PubMed Web of Science ®Google Scholar
• Nordio , P. L. , Soos , Z. G. and McConnell , H. M. 1966 . Ann. Rev. Phys. Chem. , 17 : 237
   Web of Science ®Google Scholar
• Schomaker , V. and Trueblood , K. N. 1968 . Acta Crystallogr. , B24 : 63 The largest librational amplitudes are 4.9° and 4.6° about the longitudinal in-plane molecular axes of the donor and acceptor, respectively. Bond length and bond angle corrections were on the order of their esd's. The RMS difference between the calculated and observed anisotropic thermal parameters for the HMTSF donor and the TCNQ acceptor were acceptably low at 0.0031(35) and 0.0045(48) å2, respectively, A rigid-body analysis of the thermal motion for the TCNQ molecule and the tetra-selenaethylene moiety of the HMTSF molecule was performed employing the methodology of
   Web of Science ®Google Scholar
• Hoekstra , A. , Spoelder , T. and Vos , A. 1972 . Acta Crystallogr. , B28 : 14
   Google Scholar
• Coppens , P. and Row , T. N. G. 1978 . Ann. N. Y. Acad. Sci. , 313 : 244
   Google Scholar
• Flandrois , W. and Chasseau , D. 1977 . Acta Crystallogr. , B33 : 2744
   Google Scholar