(6-Methoxy-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate

Abstract

In the title compound, C16H17NO3S2, the 2H-chromene ring is close to being planar [maximum deviation = 0.034 (2) Å] and the pyrrolidine ring is twisted about the C—C bond opposite the N atom. The dihedral angle between the ring-system planes is 75.24 (16)° and an intra­molecular C—H⋯S inter­action occurs. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and the packing also exhibits π–π inter­actions, with a distance of 3.6106 (13) Å between the centroids of the benzene rings of neighbouring mol­ecules.

Quantum chemical studies on the molecular structure, spectroscopic and electronic properties of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate

“…In the previous publication, the X-ray crystallography and IR spectra of (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate were studied [18]. In spite of its importance, mentioned above, no theoretical calculation concerning (6-Methoxy-2-oxo-2H-chromen-4-yl)-methyl pyrrolidine-1-carbodithioate has been published yet.…”

“…The title crystal is not planar. The dihedral angle between the 2H-chromene (O4/C8-C16) ring and pyrrolidine (N6/C18-C22) ring is 75.24 (16)°for X-ray [18], whereas the dihedral angle has been calculated as 67.65°for B3LYP and 70.00°for HF. The orientation of the both the rings is defined by the torsion angles C22-N6-C18-S1 (178.00°), N6-C18-S1-C17 (-170.98°), C18-S1-C17-C14 (103.72°) and S1-C17-C14-C15 (-99.35°) which have been calculated as 178.48°, -176.56°, 105.99°and -104.04°for B3LYP, and 178.56°, -174.45°, 98.78°and -107.40°for HF, respectively.…”

“…The crystal structure of the title compound is triclinic and space group is P-1. The crystal structure parameters are a = 6.7223 (2)Å, b = 8.0369 (2)Å, c = 15.4101 (5)Å, α = 75.320 (2)°, β = 88.482 (1)°, γ = 78.842 (1)°and V = 789.93 (4)Å 3 [18].…”

“…The atomic numbering scheme for the title crystal [18] and the theoretical geometric structure of the title compound are shown in Fig. 1.…”

Synthesis, Spectroscopic and Crystal Structure Studies on Ethyl 5,7-Dimethyl Coumarin-4-Acetate

“…The reactivity of C 4 -methylene group has been employed for the construction of many 4-substituted bi-heterocyclic coumarins. Solid state conformational studies on coumarin 4-acetic acid [9], ester [10,11] and dithionate [12] have been reported recently. It needs to be emphasized that the crystallographic study on esters is of considerable biological interest [13] since it determines the preferred orientation of the rotamer (Figure 1), in turn the direction of the electron pair on alkyl oxygen.…”