3-Phenyl-1-[2-(3-phenyl­isoquinolin-1-yl)­diselan­yl]isoquinoline

Hathwar, V.R.; Prabakaran, K.; Subashini, R.; Manivel, P.; Khan, F.N.

doi:10.1107/S160053680803609X

Volume 64
Part 12
Page o2295
December 2008

Received 20 October 2008
Accepted 4 November 2008
Online 8 November 2008

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.006 Å
R = 0.043
wR = 0.102
Data-to-parameter ratio = 14.0
Details

3-Phenyl-1-[2-(3-phenylisoquinolin-1-yl)diselanyl]isoquinoline

Venkatesha R. Hathwar,^a K. Prabakaran,^b R. Subashini,^b P. Manivel ^b and F. Nawaz Khan ^b ^*

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^bOrganic Chemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India
Correspondence e-mail: nawaz_f@yahoo.co.in

The complete molecule of the title compound, C₃₀H₂₀N₂Se₂, is generated by a crystallographic inversion centre at the mid-point of the Se-Se bond. The dihedral angle between the isoquinoline-1-selenol group and the phenyl ring is 14.92 (2)°. The herringbone-like packing of the structure is supported by intermolecular [pi] - [pi] stacking interactions with a shortest perpendicular distance between isoquinoline groups of 3.514 Å; the slippage between these ring systems is 0.972 Å, and the distance between the centroids of the six-membered carbon rings is 3.645 (3) Å.

Related literature

For biological properties of organoselenium compounds, see: Mugesh & Singh (2000). For chemopreventive agents in human cancer therapy, see: Sugie et al. (2000).

Experimental

Crystal data

C₃₀H₂₀N₂Se₂
M_r = 566.40
Monoclinic, C 2/c
a = 11.2441 (17) Å
b = 17.559 (3) Å
c = 13.248 (3) Å
= 115.082 (2)°
V = 2369.0 (8) Å³
Z = 4
Mo K radiation
= 3.14 mm^-1
T = 290 (2) K
0.20 × 0.14 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.585, T_max = 0.703
8668 measured reflections
2207 independent reflections
1516 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.102
S = 1.00
2207 reflections
158 parameters
H-atom parameters constrained
_max = 0.66 e Å^-3
_min = -0.22 e Å^-3

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2124 ).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA-DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks DST for Fast Track Proposal funding.

References

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Mugesh, G. & Singh, H. B. (2000). Chem. Soc. Rev. 29, 347-357.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Sugie, S., Tanaka, T. & El-Bayoumy, K. (2000). J. Health. Sci. 46, 422-425.
Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds