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

Abstract

In the title compound, C16H17NO4S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.070 (1) Å, and the morpholine ring adopts a chair conformation; the bond-angle sum for its N atom is 357.9°. The dihedral angle between the the 2H-chromene ring and the best plane through the morpholine ring is 89.09 (6)°. An intra­molecular C—H⋯S hydrogen bond occurs. In the crystal, C—H⋯O hydrogen bonds generate R 2 2(8) rings and π–π inter­actions occur between fused benzene rings of the chromene system [shortest centroid–centroid distance = 3.5487 (8) Å].

Synthesis, Characterization, and Structural Investigations of 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate

“…Meanwhile, the morpholine ring (O1/N3/C12/C13/C14/C15) in both compounds adopted chair conformations [37] with puckering parameters of Q = 0.5799 (14) Å, = 178.46 (15) • , and = 74(5) • for compound I and Q = 0.573 (2) Å, = 178.61 (19) • , and = 202 (10) • for compound II. The same ring conformations were also reported in the related compounds that consisted of morpholine ring moiety [38][39][40]. In compound I, the whole molecule was almost planar except at the terminal chloro-substituted benzene ring where it Downloaded by [Karolinska Institutet, University Library] at 05:31 29 September 2015 of crystal packing arrangement.…”

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

“…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. In the title compound, the bond lengths and angles are within normal ranges and they are comparable with those of related compounds [24][25][26]. It is well known that DFT-optimized bond lengths are usually longer and more accurate than HF due to the inclusion of electron correlation [27].…”

Crystal structure of (6-bromo-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate

“…For biological applications of coumarins and dithiocarbamates, see: D'hooghe & De Kimpe (2006); Hesse & Kirsch (2002); Jung et al (2001Jung et al ( , 2004; Lee et al (1998); Melagraki et al (2009); Schö nenberger & Lippert (1972). For standard bond lengths, see: Devarajegowda et al (2013). For a related structure and the synthesis of the title compound, see: Devarajegowda et al (2013 2= 78.515 (2) V = 780.07 (6) Å 3 Z = 2 Mo K radiation = 2.91 mm À1 T = 296 K 0.24 Â 0.20 Â 0.12 mm…”

“…For standard bond lengths, see: Devarajegowda et al (2013). For a related structure and the synthesis of the title compound, see: Devarajegowda et al (2013 2= 78.515 (2) V = 780.07 (6) Å 3 Z = 2 Mo K radiation = 2.91 mm À1 T = 296 K 0.24 Â 0.20 Â 0.12 mm…”

“…All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to the reported method (Devarajegowda et al, 2013). The compound is recrystallized by ethanol-chloroform mixture.…”