(IUCr) 2-Chloro-12-phenyl-6,7,8,9,10,11-hexahydrocycloocta[b]quinoline

Volume 64
Part 5
Page o831
May 2008

Received 4 April 2008
Accepted 5 April 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.126
Data-to-parameter ratio = 18.3
Details

2-Chloro-12-phenyl-6,7,8,9,10,11-hexahydrocycloocta[b]quinoline

Ayoob Bazgir ^a ^* and Ali Mohammad Astaraki ^a

^aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran
Correspondence e-mail: a_bazgir@yahoo.com

In the molecule of the title compound, C₂₁H₂₀ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak [pi] - [pi] interactions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.

Related literature

For general background, see: Kalluraya & Sreenivasa (1998); Doube et al. (1998); Maguire et al. (1994). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₁H₂₀ClN
M_r = 321.83
Triclinic, $[P \overline 1]$
a = 9.837 (2) Å
b = 9.980 (2) Å
c = 10.175 (2) Å
= 74.600 (17)°
= 70.575 (16)°
= 61.829 (15)°
V = 823.4 (3) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 298 (2) K
0.5 × 0.5 × 0.25 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical; shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2002) T_min = 0.889, T_max = 0.949
8123 measured reflections
3801 independent reflections
3493 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.126
S = 1.03
3801 reflections
208 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.19 e Å^-3

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2449 ).

Acknowledgements

The author is grateful to the Islamic Azad University, Dorood Branch, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Doube, D., Blouin, M., Brideau, C., Chan, C., Desmarais, S., Eithier, D., Falgueyert, J. P., Friesen, R. W., Girrard, M., Girrard, J., Tagari, P. & Yang, R. N. (1998). Bioorg. Med. Chem. Lett. 8, 1255-1260.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kalluraya, B. & Sreenivasa, S. (1998). Il Farmaco, 53, 399-404.
Maguire, M. P., Sheets, K. R., Mevety, K., Spada, A. P. & Ziberstein, A. (1994). J. Med. Chem. 37, 2129-2137.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

organic compounds