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

Zhang, X.-W.; Fan, T.

doi:10.1107/S1600536811021039

Volume 67
Part 7
Page m875
July 2011

Received 4 May 2011
Accepted 31 May 2011
Online 11 June 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.018 Å
R = 0.065
wR = 0.163
Data-to-parameter ratio = 13.4
Details

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

Xiao-Wen Zhang ^a ^* and Ting Fan ^b

^aCollege of Environment Protection and Safety Engineering, University of South China, Hengyang 421001, People's Republic of China, and ^bKey Laboratory of Pollution Control and Resource Use of Hunan Province, University of South China, Hengyang 421001, People's Republic of China
Correspondence e-mail: shawn_zhang@sina.com

In the title compound, [Bi(C₂₀H₁₇N)(ClO₄)] or C₂₀H₁₇BiClNO₄, the Bi^III ion assumes a distorted [psi] 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-HO hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis of 12-chloro-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine, see: Zhang et al. (2009). For general background, see: Shimada et al. (2004); Yin et al. (2008); Zhang et al. (2010); Tan & Zhang (2011). For related structures, see: Ohkata et al. (1989); Minoura et al. (1999).

Experimental

Crystal data

[Bi(C₂₀H₁₇N)(ClO₄)]
M_r = 579.78
Monoclinic, P 2₁ /c
a = 12.0635 (10) Å
b = 14.0755 (12) Å
c = 11.5121 (10) Å
= 107.590 (2)°
V = 1863.4 (3) Å³
Z = 4
Mo K radiation
= 9.63 mm^-1
T = 293 K
0.32 × 0.21 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan(SADABS; Bruker, 2001) T_min = 0.100, T_max = 0.145
9267 measured reflections
3279 independent reflections
2585 reflections with I > 2(I)
R_int = 0.166

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.163
S = 1.02
3279 reflections
244 parameters
H-atom parameters constrained
_max = 4.89 e Å^-3
_min = -4.14 e Å^-3

Table 1
Selected bond lengths (Å)

Bi-N1	2.387 (10)
Bi-O1	2.546 (10)
Bi-C1	2.245 (13)
Bi-C8	2.204 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O3ⁱ	0.93	2.46	3.137 (17)	130
C14-H14BO2ⁱⁱ	0.97	2.55	3.398 (16)	146
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5208 ).

Acknowledgements

The authors acknowledge the National Science Foundation of China (grant No. 51074093) for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Minoura, M., Kanamori, Y., Miyake, A. & Akiba, K. (1999). Chem. Lett. pp. 861-862.
Ohkata, K., Takemoto, S., Ohnishi, M. & Akiba, K. Y. (1989). Tetrahedron Lett. 30, 4841-4844.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shimada, S., Yamazaki, O., Tanaka, T., Suzuki, Y. & Tanaka, M. (2004). J. Organomet. Chem. 689, 3012-3023.
Tan, N. & Zhang, X. (2011). Acta Cryst. E67, m252.
Yin, S., Maruyama, J., Yamashita, T. & Shimada, S. (2008). Angew. Chem. Int. Ed. 47, 6590-6593.
Zhang, X.-W., Qiu, R.-H., Tan, N.-Y., Yin, S.-F., Xia, J., Au, C.-T. & Luo, S.-L. (2010). Tetrahedron Lett. 51, 153-156.
Zhang, X.-W., Xia, J., Yan, H.-W., Luo, S.-L., Yin, S.-F., Au, C.-T. & Wong, W.-Y. (2009). J. Organomet. Chem. 694, 3019-3026.

metal-organic compounds