[2-(2-Carboxy­phen­yl)benzoato]bis­(1,10-phenanthroline)zinc(II) 2-(2-carboxy­phen­yl)benzoate monohydrate

Wei-Wei Huang; Shi-Ping Yang

doi:10.1107/S1600536808005862

. 2008 Mar 7;64(Pt 4):m525–m526. doi: 10.1107/S1600536808005862

[2-(2-Carboxyphenyl)benzoato]bis(1,10-phenanthroline)zinc(II) 2-(2-carboxyphenyl)benzoate monohydrate

Wei-Wei Huang ^a, Shi-Ping Yang ^a,^*

PMCID: PMC2961034 PMID: 21201991

Abstract

In the title compound, [Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O, the Zn^II atom of the complex cation is six-coordinated in an octahedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxylate group from a singly deprotonated diphenic acid. The phenanthroline and carboxylate ligands act as chelating ligands. The dihedral angles between the two benzene rings in the deprotonated diphenic acid groups are 81.05 (2) (ligand) and 89.10 (2)° (anion). O—H⋯O and C—H⋯O hydrogen bonds link the components into a three-dimensional network.

Related literature

For related structures containing the diphenic acid anion, see: Wan & Zhang (2003 ▶); Vodak et al. (2001 ▶); Chui et al. (2001 ▶); Fernandes et al. (2001 ▶); Trombe et al. (2002 ▶); Xu et al. (2003 ▶); Nie et al. (2001 ▶); Sun et al. (2001 ▶).

Experimental

Crystal data

[Zn(C₁₄H₉O₄)(C₁₂H₈N₂)₂](C₁₄H₉O₄)·H₂O
M _r = 926.24
Triclinic,
a = 10.8208 (11) Å
b = 13.7475 (14) Å
c = 14.9231 (16) Å
α = 77.824 (2)°
β = 77.294 (2)°
γ = 85.052 (2)°
V = 2115.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 298 (2) K
0.46 × 0.28 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.800, T _max = 0.960
13020 measured reflections
9403 independent reflections
4505 reflections with I > 2σ(I)
R _int = 0.103

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.144
S = 0.82
9403 reflections
603 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005862/ci2560sup1.cif

e-64-0m525-sup1.cif^{(29KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005862/ci2560Isup2.hkl

e-64-0m525-Isup2.hkl^{(459.9KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Zn1—O2	2.078 (3)
Zn1—N1	2.128 (3)
Zn1—N4	2.130 (3)
Zn1—N3	2.145 (4)
Zn1—N2	2.145 (3)
Zn1—O1	2.334 (3)

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O2—Zn1—N1	102.73 (12)
O2—Zn1—N4	97.11 (12)
N1—Zn1—N4	100.12 (12)
O2—Zn1—N3	155.43 (11)
N1—Zn1—N3	101.83 (13)
N4—Zn1—N3	77.99 (14)
O2—Zn1—N2	94.88 (12)
N1—Zn1—N2	77.67 (12)
N4—Zn1—N2	167.99 (13)
N3—Zn1—N2	90.84 (13)
O2—Zn1—O1	59.17 (10)
N1—Zn1—O1	155.22 (11)
N4—Zn1—O1	98.98 (11)
N3—Zn1—O1	97.46 (11)
N2—Zn1—O1	86.71 (11)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9B⋯O7ⁱ	0.84 (4)	2.10 (5)	2.936 (6)	171 (6)
O4—H4B⋯O5ⁱⁱ	0.82	1.86	2.633 (5)	158
O9—H9A⋯O5	0.87 (5)	1.96 (6)	2.817 (6)	171 (7)
O8—H8B⋯O6	0.82	1.69	2.500 (5)	171
C3—H3⋯O1	0.93	2.55	3.130 (5)	121
C4—H4A⋯O6ⁱⁱ	0.93	2.42	3.221 (5)	144
C12—H12⋯O9	0.93	2.42	3.273 (6)	152
C16—H16⋯O7ⁱ	0.93	2.43	3.199 (7)	139
C19—H19⋯O6ⁱⁱⁱ	0.93	2.56	3.377 (5)	146
C22—H22⋯O1^iv	0.93	2.43	3.249 (6)	147

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

Acknowledgments

The authors acknowledge financial support from the Science and Technology Foundation of Shanghai (grant No. 065212050) and the Foundation of Shanghai Higher Education (grant No. 07ZZ68).

supplementary crystallographic information

Comment

In all types of carboxylic acids, diphenic acid is widely used in the construction of coordination polymers due to their capability of acting as bridging and chelating ligand in various coordination modes (Wan & Zhang, 2003). Much interest has been paid to the preparation of metal aromatic carboxylates under hydrothermal conditions (Vodak et al., 2001; Chui et al., 2001; Nie et al., 2001; Sun et al., 2001; Fernandes et al., 2001; Trombe et al. 2002; Xu et al. 2003). Recently, we have prepared the title compound and report here its crystal structure.

The asymmetric unit of the title compound consists of a [Zn(C₁₂H₈N₂)₂(C₁₄H₉O₄)]⁺ complex cation, one singly deprotonated diphenic acid anion (C₁₄H₉O₄^-) and one water molecule (Fig. 1). In the complex cation, the Zn^II atom is six-coordinated in an octahedral geometry by four N atoms from two 1,10-phenanthroline ligands and two O atoms of a carboxylate group from a diphenic acid, with Zn—N distances of 2.128 (3)–2.145 (4) Å and Zn—O distances of 2.078 (3) and 2.334 (3) Å. The N—Zn—N, N—Zn—O and O—Zn—O bond angles are in the ranges 77.99 (14)–167.99 (13)°, 86.71 (11)–155.23 (11)° and 59.17 (10)°, respectively (Table 1). The phenanthroline and diphenic acid act as chelating ligands (Table 1 and Fig.1). The dihedral angle between the two benzene rings in diphenic acid is ca 81.05 (2)° (cation) and 89.10 (2)° (anion).

Intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) link complex cations, anions and water molecules to form a three-dimensional network (Fig. 2).

Experimental

A mixture of diphenic acid (0.0484 g, 0.2 mmol), phenanthroline (0.04 g, 0.2 mmol), Zn(NO₃)₂.6H₂O (0.1 mmol) and NaOH (0.012 g, 0.3 mmol) with a molar ratio of 2/2/1/3 in H₂O—CH₃CH₂OH (v/v 4/1) (15 ml) was sealed in a Teflon-lined stainless steel Parr bomb. The bomb was heated to 433 K for 72 h and then cooled to room temperature at 5 K h^-1. A large amount of yellow crystals formed, which were collected by filtration, washed with water, and dried in air.