(IUCr) 5-Chloro-8-hydroxyquinolinium nitrate

Volume 65
Part 6
Page o1450
June 2009

Received 25 May 2009
Accepted 26 May 2009
Online 29 May 2009

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.192
Data-to-parameter ratio = 14.4
Details

5-Chloro-8-hydroxyquinolinium nitrate

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The 5-chloro-8-hydroxyquinolinium cation in the the title ion pair, C₉H₇ClNO⁺·NO₃^-, is approximately coplanar with the nitrate anion [dihedral angle = 16.1 (1)°]. Two ion pairs are hydrogen bonded (2 × O-HO and 2 × N-HO) about a center of inversion, generating an R₄⁴(14) ring.

Related literature

The 8-hydroxyquinolinium cation has been isolated as a number of salts; for the 8-hydroxyquinolinium chloride hydrate, see: Skakle et al. (2006). For the crystal structure of 5-chloro-8-hydroxyquinoline, see: Banerjee & Saha (1986).

Experimental

Crystal data

C₉H₇ClNO⁺·NO₃^-
M_r = 242.62
Monoclinic, P 2₁ /n
a = 7.4379 (3) Å
b = 11.5518 (6) Å
c = 11.2288 (5) Å
= 95.831 (3)°
V = 959.80 (8) Å³
Z = 4
Mo K radiation
= 0.40 mm^-1
T = 123 K
0.20 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.925, T_max = 0.980
6472 measured reflections
2196 independent reflections
1574 reflections with I > 2I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.192
S = 1.07
2196 reflections
153 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.20 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oO2ⁱ	0.84 (1)	1.87 (1)	2.695 (3)	169 (4)
N1-H1nO2	0.88 (1)	1.95 (1)	2.816 (3)	167 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2465 ).

Acknowledgements

I thank the University of Malaya for supporting this study.

References

Banerjee, T. & Saha, N. N. (1986). Acta Cryst. C42, 1408-1411.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2006). Acta Cryst. C62, o312-o314.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds