Methyl 4-(4-chlorophenyl)-3,3a,4,4a,5,12c-hexahydro-2-thianaphtho[1′,2′:3,2]furo[5,4-b]pyrrolizine-4a-carboxylate

In the title compound, C25H22ClNO3S, both the pyrrolidinyl and thiazolyl rings adopt envelope conformations whereas the dihydropyran ring adopts a half-chair conformation. The chlorophenyl and naphthalenyl ring systems are oriented at a dihedral angle of 59.7 (1)°. The crystal packing is stabilized by an intramolecular C—H⋯N hydrogen bond and weak intermolecular C—H⋯π interactions.

In the title compound, C 25 H 22 ClNO 3 S, both the pyrrolidinyl and thiazolyl rings adopt envelope conformations whereas the dihydropyran ring adopts a half-chair conformation. The chlorophenyl and naphthalenyl ring systems are oriented at a dihedral angle of 59.7 (1) . The crystal packing is stabilized by an intramolecular C-HÁ Á ÁN hydrogen bond and weak intermolecular C-HÁ Á Á interactions.
Cg is the centroid of the chlorophenyl ring.

Comment
In continuation of our work on the crystal structure analysis of pyrrolizine derivatives, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.
In addition to van der Waals interactions, the molecular packing is stabilized by intramolecular C-H···N hydrogen bond and intermolecular weak C-H···π interactions (Fig. 3).

Refinement
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H respectively, and U iso (H) = 1.5U eq (C) for methyl H and U iso (H) = 1.2U eq (C) for all other H atoms.  Methyl 4-(4-chlorophenyl)-3,3a,4,4a,5,12c-hexahydro-2-thianaphtho[1',2':3,2]furo [5,4-b] Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.