4-Cyano-N-ethyl-spiro-[chromene-2,4'-piperidine]-1'-carboxamide

Abstract

The title compound, C17H19N3O2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the pyran ring has a twisted conformation ((5)S4), with Q = 0.301 (3) Å, θ = 116.7 (6) and ϕ= 213.6 (7)° for mol-ecule A, and Q = 0.364 (2) Å, θ = 113.7 (3) and ϕ = 213.0 (4)° for mol-ecule B. In mol-ecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, mol-ecules A and B form very similar but separate R1(2)(7) motifs through N-H⋯O and C-H⋯O hydrogen bonds. The resulting chains along [001] are inter-linked by weaker C-H⋯O and C-H⋯π inter-actions, forming layers parallel to the bc plane.

Fig. 1.

The molecules of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at 30% probability. For the sake of clarity, H atoms are not shown.

Fig. 2.

Packing diagram of the title compound, showing formation of the separate R21 (7) motifs by molecules A and B (molecules A are shown in red, molecules B - in black). The cyano and ethyl groups were omitted for clarity as well as the H atoms not involved in the hydrogen bonding.

Fig. 3.

The layers formed by molecules B along (100) plane. Non-essential groups and most hydrogen atoms were omitted for clarity.