The first imine-bridged pyridyltetrathiafulvalene building block (TTF-CH=N-Py, 1) has been synthesized via the Schiff base condensation of formyltetrathiafulvalene and 2-aminopyridine. The preparation, X-ray crystal structure, electrochemical and magnetic characterization of a 1:1 copper complex [CuII(hfac)2(TTF-CH=N-Py)] (2) are reported. The crystal structure reveals that the imine N atom participates in chelation to the paramagnetic center, thus making this ligand an attractive precursor for the assembly of pi-d systems.

Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.003 Å; R factor = 0.044; wR factor = 0.130; data-to-parameter ratio = 14.4.The title molecule, C 12 H 11 N 3 O 2 S, adopts a cis-trans configuration of the furoyl and 6-methyl-2-pyridyl groups with respect to the thiono S atom across the thiourea C-N bonds. Intramolecular N-HÁ Á ÁO, N-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds contribute to the essential planarity of the molecular skeleton. In the crystal structure, weak intermolecular N-HÁ Á ÁS hydrogen bonds link the molecules into centrosymmetric dimers. ExperimentalCrystal data C 12 H 11 N 3 O 2 S M r = 261.30 Monoclinic, P2 1 =c a = 7.3189 (16) Å b = 18.187 (4) Å c = 9.534 (2) Å = 108.482 (4) V = 1203.6 (4) Å 3 Z = 4 Mo K radiation = 0.27 mm À1 T = 298 (2) K 0.42 Â 0.32 Â 0.31 mm Data collection Bruker SMART APEX CCD areadetector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.896, T max = 0.922 6575 measured reflections 2352 independent reflections 1959 reflections with I > 2(I) R int = 0.018