14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-indeno[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione

In the title compound, C27H28N2O3, each of the pyrrolidine rings adopts a twisted conformation, as does the cyclopentane ring. The indane ring has an r.m.s deviation of 0.0693 Å. The dihedral angle between the mean plane of the pyrrolizine ring and indane system is 82.58 (1)°. The piperidine ring has the methyl substituent in an equatorial position and adopts a twisted chair conformation. The molecular structure is stabilized by a weak intramolecular O—H⋯N interaction.

In the title compound, C 27 H 28 N 2 O 3 , each of the pyrrolidine rings adopts a twisted conformation, as does the cyclopentane ring. The indane ring has an r.m.s deviation of 0.0693 Å . The dihedral angle between the mean plane of the pyrrolizine ring and indane system is 82.58 (1) . The piperidine ring has the methyl substituent in an equatorial position and adopts a twisted chair conformation. The molecular structure is stabilized by a weak intramolecular O-HÁ Á ÁN interaction.

Comment
Pyrazole derivatives in general are well known nitrogen-containing heterocyclic compounds that have been the subject of enormous research due to their importance in various applications and their widespread potential biological and pharmacological activities such as anti-microbial (Mahajan et al., 1991), anti-viral (Baraldi et al., 1998), anti-tumor (Katayama & Oshiyama, 1997) and anti-fungal (Baraldi et al., 1998. In view of its medicinal importance we report the crystal structure of the title compound. In the title compound ( Fig. 1) The plane through the two fused rings of the indane system is slightly folded around the C14-C15 bond, as indicated by the dihedral angle between them of 5.20 (1)°. The dihedral angle between the mean plane of the pyrrolizine and indane system is 82.58 (1)°, indicating that they are nearly perpendicular to each other. The cyclopentane ring adopts a twisted conformation with puckering parameters: q 2 = 0.4839 (16) Å and Φ 2 = 17.98 (17)°. The dihedral angle between the mean planes of the pyrrolizine ring system and cyclopentane ring is 58.90 (1)°, indicating the significant curvature between the pyrrolizine and cyclopentene ring systems. The hydroxyl oxygen (O1) attached to the cyclopentane ring deviates by 1.1990 (10) Å from the mean plane of the ring. The piperidine ring with the methyl substituent in an equatorial position, adopts a twisted chair conformation with atoms C2 and C5 deviating by -0.6623 (10) Å and 0.8578 (10) Å respectively, from the mean plane defined by other atoms. In the structure, the aryl ring is in equatorial position of the attached pyrrolidine ring, as indicated by the torsion angle C7-C21-C26-C27 = -178.5 (15)°. The structure features a weak intramolecular O-H···N interaction.

Refinement
H atoms were placed at calculated positions and allowed to ride on their carrier atoms with O-H = 0.82 Å and C-H = 0.93-0.98 Å, and with U iso = 1.2U eq (C) for CH 2 and CH groups, and U iso = 1.5U eq (O, C) for OH and CH 3 groups.

Figure 1
The molecular structure of (I), showing 20% probability displacement ellipsoids and the atom-numbering scheme. Hatoms are omitted for clarity.
14a-Hydroxy-12-methyl-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octahydro-10a,14-methano-5H-  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 R-factors (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.