6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl perchlorate

In the title compound, [Bi(C20H17N)(ClO4)] or C20H17BiClNO4, the BiIII ion assumes a distorted ψ trigonal–bipyramidal geometry, with two C atoms and the electron lone pair of the Bi atom at the equatorial positions and an amine N atom and a perchlorate O atom at the apical positions. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

In the title compound, [Bi(C 20 H 17 N)(ClO 4 )] or C 20 H 17 Bi-ClNO 4 , the Bi III ion assumes a distorted trigonalbipyramidal geometry, with two C atoms and the electron lone pair of the Bi atom at the equatorial positions and an amine N atom and a perchlorate O atom at the apical positions. Weak intermolecular C-HÁ Á ÁO hydrogen bonding is present in the crystal structure.

Comment
Bismuth is a nontoxic and noncarcinogenic element and many of its compounds are low in toxicity and can be safely used in areas such as medicine, catalysis, and synthesis (Shimada et al., 2004;Yin et al., 2008;Zhang, Qiu, Tan et al., 2010). The 5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocine framework is highly stable as a organobismuth Fragment because the weakly coordination exists between bismuth and nitrogen atoms on 1,5-azabismocine (Ohkata et al.,1989;Minoura et al.,1999), and therefore, is suitable for the study of organobismuth compounds bearing various groups on the bismuth and nitrogen atom for potential uses.
In the present paper, we report the crystal structure of the title compound (Fig. 1). The central bismuth-containing part of the complex exhibits a distorted pseudo trigonal-bipyramidal structure. The C (8), C (1) atoms and a lone electron pair of the Bi atom exist at the equatorial positions while the N (1) and O (1) atoms are located at the apical positions. The Bi-C (8) and Bi-C (1) distance is 2.250 (13) Å and 2.204 (12) Å, respectively. The C (8)-Bi-C (1) angle is 92.5 (5) ° while the (19) Å also (Zhang, Xia, Yan et al., 2009).

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.93 Å for aryl, 0.98 Å methine and 0.97 Å for methylene H atoms, respectively. U iso (H)= 1.2U eq (C) for all H atoms. Fig. 1. The molecular structure of the title compound with atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All hydrogen atoms are omitted for clarity.

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.
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 > 2sigma(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.