1-Bromo-8-(phenylselenyl)naphthalene

✍ Scribed by Fuller, Amy L. ;Knight, Fergus R. ;Slawin, Alexandra M. Z. ;Woollins, J. Derek

• Publisher: International Union of Crystallography
• Year: 2007
• Tongue: English
• Weight: 445 KB
• Volume: 63
• Category: Article
• ISSN: 1600-5368
• DOI: 10.1107/s1600536807040627

✦ Synopsis

We are investigating the structures of 1,8-disubstituted naphthalenes as part of a wider study into steric crowding and hyperconjugation. In the title compound, C 16 H 11 BrSe, the SeÁ Á ÁBr distance is 3.1136 (5) A ˚. The Br and Se atoms lie 0.400 (1) and À0.421 (1) A ˚, respectively, from the mean plane of the naphthalene backbone. The heavy atoms are further accommodated by in-plane distortions in the C-C-C group between the Br and Se atoms. As expected from the heavy atom displacement, the phenylselenyl group lies on one side of the naphthalene plane, the phenyl ring being inclined at 88 to the naphthalene plane.

Related literature

For examples of sterically crowded 1,8 naphthalenes, see: Nakanishi & Hayashi (2002); Aucott et al. (2004). Experimental Crystal data C 16 H 11 BrSe M r = 362.13 Monoclinic, P2 1 =c a = 12.2378 (6) A b = 7.8921 (4) A c = 14.7367 (8) A = 110.980 (1) V = 1328.94 (12) A ˚3 Z = 4 Mo K radiation = 5.82 mm À1 T = 125.1 K 0.40 Â 0.16 Â 0.13 mm Data collection Rigaku SCXmini diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T min = 0.220, T max = 0.469 10966 measured reflections 2337 independent reflections 2043 reflections with F 2 > 2(F 2 ) R int = 0.052 Refinement R[F 2 > 2(F 2 )] = 0.033 wR(F 2