Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane

In the title compound, C25H32N4O4, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

In the title compound, C 25 H 32 N 4 O 4 , both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2) ] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2) from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5) . No classical hydrogen bonds were observed.  (2000). For puckering parameters, see Cremer & Pople (1975

Comment
1-(3,4-Methylenedioxybenzyl)piperazine or 1-piperonylpiperazine is a psychoactive drug of the piperazine class and is used to synthesise the drug, piribedil, an antiparkinsonian agent (Millan et al., 2001). The piperazine moiety is extensively employed to construct various bioactive molecules with anti-bacterial, antimalarial activity and as antipsychotic agents (Choudhary et al., 2006). A valuable insight into recent advances on antimicrobial activity of piperazine derivatives is reported (Kharb et al., 2012). Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004;Bogatcheva et al., 2006). A review on the current pharmacological and toxicological information for piperazine derivatives is described ( , 1975). One of the two five-membered dioxolane rings is planar while the other is in a slightly disordered envelope conformation (φ = 331.0 (18)°) where the mean plane of the dioxolane ring is twisted by 3.6 (1)° from that of the benzene ring. The dihedral angle between the mean planes of the two benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

Experimental
0.5 g of 1-piperonylpiperazine (Sigma-Aldrich) was dissolved in 5 ml of methanol at 333 K with stirring for 10 min and left for slow evaporation. After two days, crystal formation was not observed. For the same compound, 5 ml of dimethyl formamide was added at 333 K with stirring for 15 min and left for slow evaporation. X-ray quality crystals were obtained and were used as such (m.p.: 308-312 K.)

Refinement
H1A and H1B were located by a difference map and refined isotropically. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom-H lengths of 0.93Å (CH) or 0.97Å (CH 2 ).
Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH 2 ) times U eq of the parent atom.

Computing details
Data

Figure 1
ORTEP drawing of (I) (C 25 H 32 N 4 O 4 ) showing the labeling scheme with 30% probability displacement ellipsoids.  Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.