Complexes of the “proton sponge” 1,8-bis(dimethylamino)naphthalene (DMAN) Part 7. The occurrence of a very short asymmetric intermolecular hydrogen bond in the 100 K structure of [DMANH]+·[d-hydrogentartrate]−·trihydrate☆

Add time:08/15/2019    Source:sciencedirect.com

The structure of the complex of 1,8-bis(dimethylamino)naphthalene with d-tartaric acid, [DMANH]+·[d-hydrogentartrate]−·3H2O, has been determined by X-ray diffraction methods at 100 K. The crystals are orthorhombic, space group P212121 with a = 7.0849(3), b = 12.2115(3), c = 24.089(1) Å, V = 2084.1(1) Å3 and Z = 4. The structure, solved by direct methods, refined to R = 0.0315 for 2327 unique reflections with I >/ 2.5σ(I). As in other [DMANH]+ complexes, a proton is transferred to the DMAN residue, which results in a strong intramolecular [NH⋯N]+ H-bond (N⋯N 2.610(3) Å). The H atom in this intramolecular H-bond was found to be disordered over two positions at distances of 0.91(5) and 0.84(12) Å from the N atoms.The H-bond scheme primarily d-hydrogentartrate fragments and water molecules. One H-bond between carboxyl and carboxylate groups is extremely short (O⋯O 2.463(2) Å), but nevertheless asymmetric.

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