Abstract
In the cation of the title mol-ecular salt, C18H24N3O+·Cl-, an intra-molecular C-H⋯O hydrogen bond stabilizes the almost coplanar orientation of the aromatic ring of the indane unit and the amide plane. In the crystal, the packing is dominated by inter-molecular C-H⋯Cl hydrogen-bonding inter-actions that result in the formation of slab-like structures propagating along [010]. The slabs are linked by weak C-H⋯O inter-actions, forming layers lying parallel to (100). The methyl-ene carbon atom of the indanyl substituent is disordered over two positions with a refined occupancy ratio of 0.84 (2):0.16 (2). The crystal studied was refined as a twin with matrix [1 0 0.9, 0 0, 0 0 ]; the resulting BASF value is 0.30.
Highlights
1979), the first hemilabile NHC ligand was developed some twenty years later (McGuinness & Cavell, 2000)
The amide group is linked to one nitrogen of the imidazolium ring, N2, by a methylene group, and bears on its opposite side a indanyl substituent bound to the amide nitrogen atom N1
These are the N—C bond of the amide to its substituent on N ranging from ca 1.409 Afor a phenyl (Samantaray et al, 2007) to 1.482 Afor a t-butyl (Ray et al, 2007), and the N—C bond of the imidazolium ring to the
Summary
N-Heterocyclic carbenes (NHCs) are neutral compounds in which a 6eÀ-containing divalent carbon atom is placed between two hetero atoms They are typically derived from their parent imidazolium salts by deprotonation of the carbon atom located in between the two nitrogen atoms (Bhatia et al, 2013). Over the past two decades, N-heterocyclic carbene (NHC) ligands have been among the most exploited in organic synthesis They can be considered superior to phosphine ligands as their electronic and steric properties can be fine-tuned by simple variations in their structures (DıezGonzalez et al, 2009; Hermann, 2002; Froese et al, 2017). Attempts have been made to tune or modify the electronic and steric properties of NHCs by changing the substituent at one or both nitrogen centres. We present the synthesis and crystal structure of the chloride salt of the potentially hemilabile amido-functionalized NHC ligand precursor, 1-butyl-3-{2-[(indan-5-yl)amino]2-oxoethyl}-1H-imidazol-3-ium
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