Bis(2,2′-bipyridine)(2-hy­droxy-2,2-diphenyl­acetato)­copper(II) nitrate dihydrate

Xiao-Jun Wang; Chun Zheng; Shao-Wei Mai; Xuan Xu; Yi-Fan Luo

doi:10.1107/S1600536810035555

. 2010 Sep 11;66(Pt 10):m1245. doi: 10.1107/S1600536810035555

Bis(2,2′-bipyridine)(2-hydroxy-2,2-diphenylacetato)copper(II) nitrate dihydrate

Xiao-Jun Wang ^a, Chun Zheng ^a, Shao-Wei Mai ^a, Xuan Xu ^a,^*, Yi-Fan Luo ^a

PMCID: PMC2983227 PMID: 21587395

Abstract

In the title complex, [Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O, the Cu^II atom is coordinated by four N atoms from two 2,2′-bipyridine ligands and two O atoms from one benzilate ligand in a distorted octahedral geometry. A supramolecular network is formed via intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactions. π–π stacking interactions between neighboring pyridine rings are also present, the centroid—centroid distance being 3.808 (2) Å.

Related literature

For related structures, see: Carballo et al. (2005 ▶); Herrmann et al. (1994 ▶); Qiu et al. (2007 ▶).

Experimental

Crystal data

[Cu(C₁₄H₁₁O₃)(C₁₀H₈N₂)₂]NO₃·2H₂O
M _r = 701.18
Monoclinic,
a = 10.612 (2) Å
b = 25.758 (6) Å
c = 12.322 (3) Å
β = 108.220 (3)°
V = 3199.3 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.848, T _max = 0.872
16165 measured reflections
5750 independent reflections
3659 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.138
S = 1.00
5750 reflections
434 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536810035555/pv2323sup1.cif

e-66-m1245-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035555/pv2323Isup2.hkl

e-66-m1245-Isup2.hkl^{(281.5KB, 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
O2W—H3W⋯O5ⁱ	0.85	2.16	2.844 (6)	138
O1W—H1W⋯O4ⁱⁱ	0.85	2.07	2.884 (7)	159
O2W—H3W⋯O1Wⁱⁱⁱ	0.85	2.59	3.041 (7)	114
O1W—H2W⋯O2Wⁱⁱⁱ	0.85	2.46	3.041 (7)	126
O1W—H2W⋯O4^iv	0.85	2.28	2.856 (6)	125
O3—H3⋯O6^v	0.82	2.48	3.210 (5)	149
O3—H3⋯O1	0.82	2.10	2.597 (4)	119
C10—H10⋯O1W	0.93	2.41	3.341 (7)	174
C8—H8⋯O3^iv	0.93	2.54	3.389 (6)	152
C4—H4⋯O5^vi	0.93	2.59	3.488 (6)	162
C12—H12⋯O5^vii	0.93	2.38	3.285 (7)	165
C14—H14⋯O1^viii	0.93	2.56	3.420 (6)	155
C17—H17⋯O1^viii	0.93	2.39	3.270 (5)	159

Open in a new tab

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

Acknowledgments

The authors acknowledge the Natural Science Foundation of Guangdong Province (No. 9151063101000037) for support of this work.

supplementary crystallographic information

Comment

Hydrogen-bonding interactions between ligands are specific and directional. In this context, 2,2'-bipyridine and benzilic acid are excellent candidates for construction of three-demensional network motifs, and can simultaneously coordinate metal ions (Carballo et al., 2005; Herrmann et al., 1994; Qiu et al., 2007). Herein, we report the crystal structure of a new coordination polymer, (I).

In (I), the Cu^II centre is coordinated by two oxygen atoms from one benzilate ligand and four N atoms from two 2,2'-bipyridine ligands (Fig. 1), and represents a distorted octahedral geometry. The Cu—N distances range from 1.982 (3) to 2.174 (3) Å, and the Cu—O distances are 1.982 (3) and 2.744 (3) Å, respectively. However, the O—Cu—N and N—Cu—N angles fall in the range from 89.06 (1) to 158.18 (1) ° and 77.87 (1) to 175.10 (1) °, respectively. Intermolecular O—H···O and C—H···O hydrogen bonding interactions (Table 1) link each asymmetric unit to form a three-dimensional supramolecular network motif (Fig. 2) in (0 0 1) plane, which is stabilized by π-π stacking interactions between neighboring pyridyl rings (the centriod—centriod distance is 3.808 Å).

Experimental

A mixture of CuNO₃ (0.063 g, 0.5mmol), 2,2'-bipyridine (0.078 g; 0.5 mmol), benzilic acid (0.114 g; 0.5 mmol), water (10 mL) was stirred vigorously for 60 min and the blue block crystals were obtained by evaporating mother liquor.