Bis(8-hy­droxy-2-methyl­quinolinium) bis­(pyridine-2,6-dicarboxyl­ato)­nickelate(II) methanol monosolvate monohydrate

Hossein Aghabozorg; Ahmad Gholizadeh; Masoud Mirzaei; Behrouz Notash; Niloofar Moshki

doi:10.1107/S1600536811021015

. 2011 Jun 11;67(Pt 7):m891–m892. doi: 10.1107/S1600536811021015

Bis(8-hydroxy-2-methylquinolinium) bis(pyridine-2,6-dicarboxylato)nickelate(II) methanol monosolvate monohydrate

Hossein Aghabozorg ^a, Ahmad Gholizadeh ^a,^*, Masoud Mirzaei ^b, Behrouz Notash ^c, Niloofar Moshki ^a

PMCID: PMC3152105 PMID: 21836882

Abstract

In the title compound, (C₁₀H₁₀NO)₂[Ni(C₇H₃NO₄)₂]·CH₃OH·H₂O, the coordination geometry of the Ni^II atom can be described as distorted octahedral. In the crystal, noncovalent interactions play an important role in the stabilization of the structure, involving O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds and π–π stacking interactions between the pyridine rings of the pyridine-2,6-dicarboxylate ligands [centroid–centroid distance = 3.7138 (15) Å] and between the 8-hydroxy-2-methylquinolinium cations [centroid–centroid distances = 3.6737 (15), 3.4434 (14), 3.6743 (15), 3.7541 (16), 3.5020 (15) and 3.7947 (15) Å].

Related literature

For general background to proton transfer compounds based on carboxylic acid derivatives, see: Aghabozorg et al. (2008 ▶); Eshtiagh-Hosseini, Aghabozorg et al. (2010 ▶); Eshtiagh-Hosseini, Alfi et al. (2010 ▶); Eshtiagh-Hosseini, Yousefi et al. (2010 ▶). For related structures, see: Aghabozorg et al. (2011 ▶); Pasdar et al. (2011 ▶).

Experimental

Crystal data

(C₁₀H₁₀NO)₂[Ni(C₇H₃NO₄)₂]·CH₄O·H₂O
M _r = 759.34
Triclinic,
a = 10.100 (2) Å
b = 12.733 (3) Å
c = 14.638 (3) Å
α = 115.45 (3)°
β = 98.73 (3)°
γ = 95.89 (3)°
V = 1650.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 120 K
0.50 × 0.50 × 0.23 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T _min = 0.723, T _max = 0.856
18115 measured reflections
8795 independent reflections
7132 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.138
S = 1.05
8795 reflections
492 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.35 e Å⁻³
Δρ_min = −1.17 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021015/hy2430sup1.cif

e-67-0m891-sup1.cif^{(30.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021015/hy2430Isup2.hkl

e-67-0m891-Isup2.hkl^{(430.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O7ⁱ	0.93	2.54	3.164 (3)	124
C11—H11⋯O1ⁱⁱ	0.93	2.52	3.154 (3)	126
C15—H15A⋯O4ⁱⁱⁱ	0.96	2.47	3.398 (3)	162
C17—H17⋯O6^iv	0.93	2.27	3.155 (3)	158
C21—H21⋯O6	0.93	2.58	3.344 (3)	139
C25—H25A⋯O8ⁱⁱ	0.96	2.50	3.169 (3)	127
C27—H27⋯O4^v	0.93	2.42	3.298 (3)	158
N3—H3A⋯O11ⁱⁱⁱ	0.82 (3)	1.92 (3)	2.732 (3)	171 (3)
N4—H4A⋯O8ⁱⁱ	0.86 (3)	1.89 (3)	2.706 (3)	157 (3)
O9—H9A⋯O5^v	0.82	1.75	2.574 (2)	178
O10—H10A⋯O2^vi	0.82	1.76	2.562 (2)	166
O11—H11A⋯O3	0.87 (4)	1.83 (4)	2.699 (2)	171 (4)
O12—H12A⋯O7	0.82 (2)	2.05 (2)	2.852 (4)	167 (5)
O12—H12B⋯O4ⁱ	0.82 (2)	2.32 (3)	3.049 (4)	149 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors thank the Faculty of Chemistry, Islamic Azad University, North Tehran Branch, for supporting this work.

supplementary crystallographic information

Comment

Recently, we have defined a plan to prepare water soluble proton transfer compounds as novel self-assembled systems that can function as suitable ligands in the synthesis of metal complexes. In this regard, we have reported cases in which proton transfers from pyridine-2,6-dicarboxylic acid (pydcH₂) to different amine base ligands (Eshtiagh-Hosseini, Aghabozorg et al., 2010; Eshtiagh-Hosseini, Alfi et al., 2010; Eshtiagh-Hosseini, Yousefi et al., 2010). This research plan has resulted in the formation of some novel proton transfer compounds based on carboxylic acid derivatives. For more details and related literature see our review article (Aghabozorg et al., 2008).

We have recently reported an isostructural Cu(II) compound with formula (8hmqH)₂[Cu(pydc)₂].CH₃OH.H₂O (8hmq = 8-hydroxy-2-methylquinoline) (Aghabozorg et al., 2011) and a related Ni(II) compound (Pasdar et al., 2011). The molecular structure of the title compound is presented in Fig. 1. The Ni^II atom is six-coordinated by two pydc ligands. As it can be seen, atoms N1 and N2 of the two pydc ligands occupy the axial positions, while atoms O1, O3, O5, and O7 form the equatorial plane, with Ni—O distances ranging from 2.1247 (16) to 2.1449 (16) Å. The N1—Ni1—N2 angle [173.76 (7)°] deviates from linearity. Therefore, the geometry of the resulting NiN₂O₄ coordination can be described as distorted octahedral. In the crystal structure, non-covalent interactions play an important role in the stabilization of the structure, involving O—H···O, N—H···O and weak C—H···O hydrogen bonds and π–π stacking interactions between the pyridine rings of the pydc ligands [centroid–centroid distance = 3.7138 (15) Å] and between the 8hmqH cations [centroid–centroid distances = 3.6737 (15), 3.4434 (14), 3.6743 (15), 3.7541 (16), 3.5020 (15) and 3.7947 (15) Å].

Experimental

8-Hydroxy-2-methylquinoline (0.320 g, 2 mmol) in methanol (10 ml) and 2,6-pyridine dicarboxylic acid (0.170 g, 1 mmol) in methanol (10 ml) were mixed and stirred until a clear solution was obtained. A solution of Ni(NO₃)₂.6H₂O (0.145 g, 0.5 mmol) in methanol (5 ml) was added to the mixture and stirred for 30 min. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation after two weeks.