1,10-Phenanthrolinium 4-chloro-2-hydroxy­benzoate–1,10-phenanthroline–4-chloro-2-hydroxy­benzoic acid (1/1/1)

Shen, H.; Nie, J.-J.; Xu, D.-J.

doi:10.1107/S1600536808015110

Volume 64
Part 6
Pages o1146-o1147
June 2008

Received 19 May 2008
Accepted 19 May 2008
Online 24 May 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.039
wR = 0.099
Data-to-parameter ratio = 13.9
Details

1,10-Phenanthrolinium 4-chloro-2-hydroxybenzoate-1,10-phenanthroline-4-chloro-2-hydroxybenzoic acid (1/1/1)

Hong Shen,^a Jing-Jing Nie ^a and Duan-Jun Xu ^a ^*

^aDepartment of Chemistry, Zhejiang University, People's Republic of China
Correspondence e-mail: xudj@mail.hz.zj.cn

The title compound, C₁₂H₉N₂⁺·C₇H₄ClO₃^-·C₁₂H₈N₂·C₇H₅ClO₃, contains one phenanthrolinium (Hphen) cation, one phenanthroline (phen) molecule, one 4-chloro-2-hydroxybenzoate anion (hcba) and one 4-chloro-2-hydroxybenzoic acid (Hhcba) molecule in the asymmetric unit. The phen molecule is approximately parallel to Hphen, making a dihedral angle of 1.98 (6)°. The centroid-centroid distance between pyridine rings of adjacent phen and Hphen species is 3.7718 (15) Å, and that between the benzene and pyridine rings of adjacent phen and Hphen species is 3.7922 (16) Å, indicative of [pi] - [pi] stacking interactions. The crystal structure contains an extensive network of classical (O-HO, N-HN and O-HCl) and weak (C-HO and C-HN) hydrogen bonds. Finally, C-H [pi] interactions are seen between Hphen and hcba and between phen and Hhcba in the crystal structure. The hydroxy group of the anion is disordered over the two sites ortho to the carboxylate group in a 0.75:0.25 ratio.

Related literature

For general background, see: Su & Xu (2004); Pan et al. (2006). For a related structure, see: Fu et al. (2005).

Experimental

Crystal data

C₁₂H₉N₂⁺·C₇H₄ClO₃^-·C₁₂H₈N₂·C₇H₅ClO₃
M_r = 705.53
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0627 (6) Å
b = 19.6005 (15) Å
c = 20.7929 (17) Å
V = 3286.0 (4) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 295 (2) K
0.43 × 0.37 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
37126 measured reflections
6394 independent reflections
4326 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.098
S = 0.98
6394 reflections
460 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.14 e Å^-3
Absolute structure: Flack (1983), 2739 Friedel pairs
Flack parameter: -0.09 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO5	0.88	1.61	2.484 (2)	173
N1-H1NN3ⁱ	0.85	2.14	2.915 (3)	153
O3-H3ACl1ⁱⁱ	0.95	2.66	3.1714 (19)	114
O3-H3AO2	0.95	1.86	2.603 (3)	133
O6A-H6AO4	0.94	1.74	2.584 (3)	148
O6B-H6BO5	0.82	1.80	2.494 (7)	142
C5-H5O2ⁱⁱⁱ	0.93	2.50	3.404 (3)	164
C12-H12O4ⁱⁱ	0.93	2.51	3.381 (3)	157
C21-H21N2ⁱ	0.93	2.51	3.345 (4)	150
C22-H22O1^iv	0.93	2.54	3.220 (4)	130
C37-H37O4	0.93	2.60	3.430 (3)	150
C25-H25Cg1	0.93	2.65	3.571 (3)	174
C40-H40Cg2	0.93	2.63	3.489 (3)	154
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z; (iii) x-1, y, z; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C8-C13 benzene ring and Cg2 is the centroid of the C1-C6 benzene ring.

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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: HB2735 ).

Acknowledgements

The work was supported by the ZIJIN project of Zhejiang University, China.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fu, A.-Y., Wang, D.-Q. & Zhang, C.-L. (2005). Acta Cryst. E61, o3119-o3121.
Pan, T.-T., Liu, J.-G. & Xu, D.-J. (2006). Acta Cryst. E62, m1597-m1599.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Su, J.-R. & Xu, D.-J. (2004). J. Coord. Chem. 57, 223-229.

organic compounds