Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 5 (May 2009)

organic compounds

Acta Cryst. (2009). C65, o248-o252 [ doi:10.1107/S0108270109013456 ]

1,3,5-Triphenyladamantane and 1,3,5,7-tetraphenyladamantane

I. Boldog, A. B. Lysenko, E. B. Rusanov, A. N. Chernega and K. V. Domasevitch

Abstract: In 1,3,5-triphenyladamantane, C₂₈H₂₈, (I), and 1,3,5,7-tetraphenyladamantane, C₃₄H₃₂, (II), the molecules possess symmetries 3 and $\overline{4}$ , and are situated across threefold and fourfold improper axes, respectively. The molecules aggregate by means of extensive C-H [pi] interactions. In (I), the pyramidal shape of the molecules dictates the formation of dimers through a `sixfold phenyl embrace' pattern. The dimers are linked to six close neighbors and constitute a primitive cubic net [H [pi] = 2.95 (2) and 3.02 (2) Å]. Compound (II) is isomorphous with tetraphenyl derivatives EPh₄ of group 14 (E = C-Pb) and ionic salts [EPh₄][BPh₄] (E = P, As and Sb). The multiple C-H [pi] interactions arrange the molecules into chains, with a concerted action of CH (phenyl) and CH₂ (adamantane) groups as donors [H [pi] = 3.15 (2) and 3.44 (2) Å, respectively]. The additional interactions with the methylene groups (four per molecule) are presumably important for explaining the high melting point and insolubility of (II) compared with the EPh₄ analogs.

Formula: C₂₈H₂₈ and C₃₄H₃₂


	Structure factor file (CIF format) (65.4 kbytes) [ doi:10.1107/S0108270109013456/sf3104Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (40.1 kbytes) [ doi:10.1107/S0108270109013456/sf3104IIsup3.hkl ] Contains datablock II

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