2-(2-Quinol­yl)quinolinium nitrate

Abedi, A.; Bahrami Shabestari, A.; Amani, V.

doi:10.1107/S1600536808012579

Volume 64
Part 6
Page o990
June 2008

Received 17 April 2008
Accepted 29 April 2008
Online 3 May 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.057
wR = 0.137
Data-to-parameter ratio = 16.3
Details

2-(2-Quinolyl)quinolinium nitrate

Anita Abedi,^a Arezoo Bahrami Shabestari ^a and Vahid Amani ^b ^*

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
Correspondence e-mail: v_amani2002@yahoo.com

In the cation of the title compound, C₁₈H₁₃N₂⁺·NO₃^-, the two bicyclic ring systems form a dihedral angle of 3.84 (4)°. The nitrate anion is disordered over two orientations in a 0.9:0.1 ratio. In the crystal structure, the cations form stacks along the a axis, with short intermolecular contacts [CC = 3.330 (3) and 3.345 (4) Å], and link to the anions via N-HO hydrogen bonds.

Related literature

For related literature, see: Smith et al. (1999); Zafar et al. (2000); Rafizadeh et al. (2006); Yousefi et al. (2007); Parlow & Hartl (1979).

Experimental

Crystal data

C₁₈H₁₃N₂⁺·NO₃^-
M_r = 319.31
Monoclinic, P 2₁ /c
a = 6.9756 (6) Å
b = 10.6408 (9) Å
c = 19.1226 (15) Å
= 94.399 (2)°
V = 1415.2 (2) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 120 (2) K
0.45 × 0.30 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: none
15078 measured reflections
3739 independent reflections
2115 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.136
S = 0.97
3739 reflections
229 parameters
3 restraints
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NO1	0.91	1.92	2.766 (2)	153

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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: CV2401 ).

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Parlow, A. & Hartl, H. (1979). Acta Cryst. B35, 1930-1933.
Rafizadeh, M., Aghayan, H. & Amani, V. (2006). Acta Cryst. E62, o5034-o5035.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Pascoe, C. E., Kennard, C. H. L. & Byriel, K. A. (1999). Aust. J. Chem. 52, 71-74.
Yousefi, M., Amani, V. & Khavasi, H. R. (2007). Acta Cryst. E63, o3782.
Zafar, A., Geib, S. J., Hamuro, Y., Carr, A. J. & Hamilton, A. D. (2000). Tetrahedron, 56, 8419-8427.

organic compounds