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The reactions of N-heterocyclic carbene Cu I and Ag I halides with potassium thio- or seleno-cyanate gave unexpected products. The attempted substitution reaction of bromido-(1,3-dibenzyl-4,5-di-phenyl-imidazol-2-yl-idene)silver (NHC*-Ag-Br) with KSCN yielded bis-[bis-(1,3-dibenzyl-4,5-di-phenyl-imidazol-2-yl-idene)silver(I)] tris-(thio-cyanato)-argentate(I) diethyl ether disolvate, [Ag(C 29 H 24 N 2 ) 2 ][Ag(NCS) 3 ]·2C 4 H 10 O or [NHC* 2 Ag] 2 [Ag(SCN) 3 ]·2Et 2 O, ( 1 ), while reaction with KSeCN led to bis-(μ-1,3-dibenzyl-4,5-diphenyl-2-seleno-imidazole-κ 2  Se : Se )bis-[bromido-(1,3-dibenzyl-4,5-diphenyl-2-seleno-imid-azole-κ Se )silver(I)] di-chloro-methane hexa-solvate, [Ag 2 Br 2 (C 29 H 24 N 2 Se) 4 ]·6CH 2 Cl 2 or (NHC*Se) 4 Ag 2 Br 2 ·6CH 2 Cl 2 , ( 2 ), via oxidation of the NHC* fragment to 2-seleno-imidazole. This oxidation was observed again in the reaction of NHC*-Cu-Br with KSeCN, yielding catena -poly[[[(1,3-dibenzyl-4,5-diphenyl-2-seleno-imidazole-κ Se )copper(I)]-μ-cyanido-κ 2  C : N ] aceto-nitrile monosolvate], {[Cu(CN)(C 29 H 24 N 2 Se)]·C 2 H 3 N}  n  or NHC*Se-CuCN·CH 3 CN, ( 3 ). Compound ( 1 ) represents an organic/inorganic salt with Ag I in a linear coordination in each of the two cations and in a trigonal coordination in the anion, accompanied by diethyl ether solvent mol-ecules. The tri-blade boomerang-shaped complex anion [Ag(SCN) 3 ] 2- present in ( 1 ) is characterized by X-ray diffraction for the first time. Compound ( 2 ) comprises an isolated centrosymmetric mol-ecule with Ag I in a distorted tetra-hedral BrSe 3 coordination, together with di-chloro-methane solvent mol-ecules. Compound ( 3 ) exhibits a linear polymeric 1  ∞ [Cu-C≡N-Cu-] chain structure with a seleno-imidazole moiety additionally coordinating to each Cu I atom, and completed by aceto-nitrile solvent mol-ecules. Electron densities associated with an additional ether solvent mol-ecule in ( 1 ) and two additional di-chloro-methane solvent mol-ecules in ( 2 ) were removed with the SQUEEZE procedure [Spek (2015 ▸). Acta Cryst. C 71 , 9-18] in PLATON .

Unexpected reactions of NHC*—CuI and —AgI bromides with potassium thio- or selenocyanate

Unexpected reactions of NHC*—Cu^I and —Ag^I bromides with potassium thio- or selenocyanate