Bis(1-methyl-1H-imidazole-κN3)bis­[2-(naphthalen-1-yl)acetato-κO]copper(II) monohydrate

Yin, F.-J.; Han, L.-J.; Yang, S.-P.; Xu, X.-Y.; Gu, Y.

doi:10.1107/S1600536811049439

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1821

https://doi.org/10.1107/S1600536811049439

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Bis(1-methyl-1H-imidazole-κN³)bis[2-(naphthalen-1-yl)acetato-κO]copper(II) monohydrate

Fu-Jun Yin,^a ^* Li-Jun Han,^b Shu-Ping Yang,^c Xing-You Xu ^d and Yu Gu ^e

^aJiangsu Marine Resources Development, Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bDepartment of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^cDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^dDepartment of Chemical Engineering, Huaiyin Insititute of Technology, Huaiyin 223003, People's Republic of China, and ^eQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: yfj1999@126.com

(Received 10 November 2011; accepted 19 November 2011; online 25 November 2011)

In the crystal structure of the title compound, [Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O, the Cu^II atom is coordinated by two 2-(naphthalen-1-yl)acetate anions and two 1-methylimidazole ligands, giving monomeric complexes with a square-planar coordination environment. Two complex molecules and two water molecules form a centrosymmetric ring system via O—H⋯O hydrogen bonds.

Related literature

For the pharmacological potential of metal complexes with imidazole, see: Boiani & Gonzales (2005 ); Parshina & Trofimov (2011 ). For the coordination chemistry of 1-naphthylacetate ligands, see: Yin et al. (2010 ); Chen et al. (2004 ); Yang et al. (2008 ); Tang et al. (2006 ); Ji et al. (2011 ).

Experimental

Crystal data

[Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O
M_r = 616.16
Triclinic, $[P \overline 1]$
a = 8.7213 (10) Å
b = 12.8689 (14) Å
c = 13.5787 (15) Å
α = 107.223 (1)°
β = 90.295 (2)°
γ = 90.931 (1)°
V = 1455.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.843, T_max = 0.843
11175 measured reflections
5094 independent reflections
3534 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.102
S = 1.03
5094 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1	0.85	1.97	2.789 (3)	163
O1W—H1WB⋯O3ⁱ	0.85	2.07	2.904 (3)	167
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker 2007 ); cell refinement: SAINT (Bruker 2007); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049439/im2340sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049439/im2340Isup2.hkl

checkCIF report

Comment top

Self-assembly of supramolecular architectures based on naphthalene-1-yl-acetate ligands has attracted much attention during recent decades (Yin et al., 2010; Chen et al., 2004; Yang et al., 2008; Tang et al.,2006; Ji et al., 2011). Recent studies reveal that metal complexes with substituted imidazole and carboxylate ligands are interesting for medicinal chemists who explore their various pharmacological potentials (Boiani & Gonzales, 2005; Parshina & Trofimov, 2011). The crystal structure of the title compound was determined as part of an ongoing study on the properties of copper complexes containing imidazole ligands.

In the crystal structure of the title compound [Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]H₂O, each copper cation is coordinated by two N atoms of different 1-methylimidazole ligands and by two carboxyl O atoms of distinct naphthalene-1-yl-acetate anions within a square planar coordination sphere (Fig. 1). The Cu—N and Cu—O bond lengths are 1.985 (3) and 1.974 (2) Å, respectively. The asymmetric unit consits of one Cu^II cation, two neutral imidazole ligands, two anionic carboxylate ligands and one lattic water in general positions. It is noteworthy that there exist strong hydrogen-bonding interactions (Table 1, Fig.2) involving the carboxy group oxygen atoms of 1-naphthylacetate ligands as well as water molecules. The molecules fomr centrosymmetric ring systems by O—H···O hydrogen bonds

Related literature top

For the pharmacological potential of metal complexes with imidazole, see: Boiani & Gonzales (2005); Parshina & Trofimov (2011). For the coordination chemistry of 1-naphthylacetate ligands, see: Yin et al. (2010); Chen et al. (2004); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011).

Experimental top

The title compound was synthesized by the reaction of Cu(NO₃)₂ × 3 H₂O (72.3 mg, 0.3 mmol), naphthalene-1-yl-acetic acid (93 mg, 0.5 mmol), 1-methylimidazole (32.8 mg, 0.4 mmol) and NaOH (20 mg, 0.5 mmol) in 6 mL of a water-ethanol (2:1) mixture under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 140°C for three days. After cooling green crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol (yield: 38.7% based on Cu(NO₃)₂ × 3 H₂O ).

Structure description top

For the pharmacological potential of metal complexes with imidazole, see: Boiani & Gonzales (2005); Parshina & Trofimov (2011). For the coordination chemistry of 1-naphthylacetate ligands, see: Yin et al. (2010); Chen et al. (2004); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011).

Computing details top

Data collection: APEX2 (Bruker 2007); cell refinement: SAINT (Bruker 2007); data reduction: SAINT'(Bruker 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Crystal structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Centrosymmetric ring system of the title compound including lattice water molecules. Hydrogen bonds are shown as dashed lines, and H atoms not involved in hydrogen bonding are omitted for clarity.

Bis(1-methyl-1H-imidazole-κN³)bis[2-(naphthalen-1-yl)acetato- κO]copper(II) monohydrate top

Crystal data top

[Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O	Z = 2
M_r = 616.16	F(000) = 642
Triclinic, P1	D_x = 1.406 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7213 (10) Å	Cell parameters from 1644 reflections
b = 12.8689 (14) Å	θ = 2.3–19.2°
c = 13.5787 (15) Å	µ = 0.80 mm⁻¹
α = 107.223 (1)°	T = 298 K
β = 90.295 (2)°	Prism, green
γ = 90.931 (1)°	0.20 × 0.20 × 0.20 mm
V = 1455.4 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	5094 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.843, T_max = 0.843	k = −15→15
11175 measured reflections	l = −15→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0371P)² + 0.1784P] where P = (F_o² + 2F_c²)/3
5094 reflections	(Δ/σ)_max = 0.001
381 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O	γ = 90.931 (1)°
M_r = 616.16	V = 1455.4 (3) Å³
Triclinic, P1	Z = 2
a = 8.7213 (10) Å	Mo Kα radiation
b = 12.8689 (14) Å	µ = 0.80 mm⁻¹
c = 13.5787 (15) Å	T = 298 K
α = 107.223 (1)°	0.20 × 0.20 × 0.20 mm
β = 90.295 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5094 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3534 reflections with I > 2σ(I)
T_min = 0.843, T_max = 0.843	R_int = 0.040
11175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
5094 reflections	Δρ_min = −0.31 e Å⁻³
381 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7153 (4)	0.7870 (3)	0.6104 (3)	0.0395 (8)
C2	0.7391 (4)	0.6657 (2)	0.5639 (3)	0.0490 (9)
H2A	0.6505	0.6333	0.5219	0.059*
H2B	0.7486	0.6320	0.6187	0.059*
C3	0.8829 (4)	0.6438 (2)	0.4976 (3)	0.0444 (8)
C4	0.8703 (4)	0.6226 (3)	0.3940 (3)	0.0500 (9)
H4	0.7735	0.6199	0.3643	0.060*
C5	0.9998 (5)	0.6045 (3)	0.3301 (3)	0.0630 (11)
H5	0.9880	0.5891	0.2590	0.076*
C6	1.1423 (5)	0.6098 (3)	0.3728 (3)	0.0587 (10)
H6	1.2279	0.5991	0.3307	0.070*
C7	1.1612 (4)	0.6314 (3)	0.4797 (3)	0.0470 (9)
C8	1.0292 (4)	0.6489 (2)	0.5452 (3)	0.0435 (8)
C9	1.0541 (4)	0.6709 (3)	0.6524 (3)	0.0479 (9)
H9	0.9703	0.6810	0.6960	0.058*
C10	1.1973 (5)	0.6777 (3)	0.6928 (3)	0.0639 (11)
H10	1.2109	0.6938	0.7637	0.077*
C11	1.3237 (5)	0.6609 (3)	0.6291 (4)	0.0746 (13)
H11	1.4216	0.6652	0.6577	0.090*
C12	1.3065 (4)	0.6384 (3)	0.5264 (4)	0.0653 (11)
H12	1.3932	0.6273	0.4852	0.078*
C13	0.7022 (4)	1.1979 (3)	0.8398 (3)	0.0435 (8)
C14	0.6624 (4)	1.3180 (2)	0.8668 (2)	0.0486 (9)
H14A	0.7555	1.3604	0.8673	0.058*
H14B	0.5946	1.3286	0.8139	0.058*
C15	0.5856 (4)	1.3596 (3)	0.9707 (3)	0.0461 (9)
C16	0.6705 (5)	1.4139 (3)	1.0546 (3)	0.0587 (10)
H16	0.7744	1.4269	1.0472	0.070*
C17	0.6043 (6)	1.4509 (3)	1.1527 (3)	0.0729 (13)
H17	0.6643	1.4883	1.2093	0.088*
C18	0.4542 (6)	1.4321 (3)	1.1650 (3)	0.0736 (13)
H18	0.4120	1.4561	1.2304	0.088*
C19	0.3595 (5)	1.3768 (3)	1.0802 (3)	0.0572 (10)
C20	0.4261 (4)	1.3412 (3)	0.9806 (3)	0.0448 (9)
C21	0.3277 (5)	1.2891 (3)	0.8967 (3)	0.0597 (10)
H21	0.3683	1.2649	0.8308	0.072*
C22	0.1773 (5)	1.2735 (4)	0.9093 (4)	0.0807 (13)
H22	0.1156	1.2400	0.8524	0.097*
C23	0.1130 (6)	1.3074 (4)	1.0074 (5)	0.0928 (16)
H23	0.0093	1.2948	1.0157	0.111*
C24	0.2010 (6)	1.3585 (4)	1.0903 (4)	0.0837 (15)
H24	0.1565	1.3820	1.1551	0.100*
C25	0.5448 (4)	0.8706 (3)	0.8592 (3)	0.0524 (9)
H25	0.6224	0.8212	0.8566	0.063*
C26	0.4117 (4)	0.8717 (3)	0.9070 (3)	0.0579 (10)
H26	0.3797	0.8238	0.9427	0.069*
C27	0.4195 (4)	1.0032 (3)	0.8372 (3)	0.0518 (9)
H27	0.3913	1.0633	0.8169	0.062*
C28	0.1776 (4)	0.9878 (4)	0.9308 (3)	0.0884 (15)
H28A	0.1519	1.0545	0.9172	0.133*
H28B	0.1746	0.9981	1.0037	0.133*
H28C	0.1050	0.9318	0.8964	0.133*
C29	0.9660 (4)	1.1131 (3)	0.6535 (3)	0.0530 (10)
H29	0.9081	1.1756	0.6656	0.064*
C30	1.1062 (4)	1.1006 (3)	0.6125 (3)	0.0574 (10)
H30	1.1621	1.1517	0.5906	0.069*
C31	1.0373 (4)	0.9532 (3)	0.6472 (3)	0.0486 (9)
H31	1.0398	0.8832	0.6536	0.058*
C32	1.2957 (4)	0.9490 (3)	0.5669 (3)	0.0702 (12)
H32A	1.2955	0.8747	0.5679	0.105*
H32B	1.3799	0.9881	0.6081	0.105*
H32C	1.3064	0.9513	0.4973	0.105*
Cu1	0.72561 (4)	0.98739 (3)	0.73588 (3)	0.03873 (15)
N1	0.5513 (3)	0.9531 (2)	0.8147 (2)	0.0434 (7)
N2	0.9208 (3)	1.0192 (2)	0.67509 (19)	0.0403 (7)
N3	0.3314 (3)	0.9560 (2)	0.8930 (2)	0.0527 (8)
N4	1.1514 (3)	0.9992 (2)	0.6089 (2)	0.0461 (7)
O1	0.6406 (3)	0.83829 (19)	0.56361 (17)	0.0543 (6)
O2	0.7793 (2)	0.83265 (16)	0.69796 (17)	0.0433 (6)
O3	0.6513 (2)	1.13568 (16)	0.75272 (17)	0.0444 (6)
O4	0.7809 (3)	1.16518 (18)	0.89921 (18)	0.0540 (6)
O1W	0.5269 (3)	0.7509 (2)	0.36319 (19)	0.0803 (9)
H1WA	0.5433	0.7839	0.4266	0.120*
H1WB	0.4770	0.7933	0.3378	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0288 (18)	0.0333 (19)	0.053 (2)	0.0010 (15)	0.0151 (17)	0.0078 (17)
C2	0.0364 (19)	0.0341 (19)	0.068 (2)	0.0010 (16)	0.0061 (17)	0.0025 (17)
C3	0.043 (2)	0.0273 (18)	0.057 (2)	0.0033 (15)	0.0049 (18)	0.0016 (16)
C4	0.050 (2)	0.0354 (19)	0.053 (2)	0.0078 (17)	−0.0026 (18)	−0.0050 (17)
C5	0.082 (3)	0.046 (2)	0.054 (2)	0.016 (2)	0.010 (2)	0.0012 (19)
C6	0.057 (3)	0.047 (2)	0.072 (3)	0.0129 (19)	0.023 (2)	0.016 (2)
C7	0.039 (2)	0.0324 (19)	0.072 (3)	0.0081 (16)	0.0143 (19)	0.0175 (18)
C8	0.040 (2)	0.0250 (17)	0.066 (3)	0.0041 (15)	0.0048 (18)	0.0145 (17)
C9	0.048 (2)	0.041 (2)	0.057 (2)	0.0063 (17)	0.0068 (18)	0.0174 (18)
C10	0.061 (3)	0.064 (3)	0.073 (3)	0.005 (2)	−0.011 (2)	0.029 (2)
C11	0.045 (3)	0.081 (3)	0.109 (4)	0.003 (2)	−0.009 (3)	0.046 (3)
C12	0.040 (2)	0.071 (3)	0.094 (3)	0.011 (2)	0.013 (2)	0.037 (3)
C13	0.049 (2)	0.038 (2)	0.045 (2)	0.0085 (17)	0.0225 (18)	0.0130 (18)
C14	0.060 (2)	0.0341 (19)	0.050 (2)	0.0078 (17)	0.0128 (18)	0.0092 (17)
C15	0.065 (3)	0.0293 (18)	0.044 (2)	0.0163 (18)	0.0044 (19)	0.0098 (17)
C16	0.069 (3)	0.039 (2)	0.063 (3)	0.0108 (19)	−0.006 (2)	0.007 (2)
C17	0.110 (4)	0.048 (2)	0.051 (3)	0.023 (3)	−0.017 (3)	−0.001 (2)
C18	0.125 (4)	0.054 (3)	0.043 (3)	0.044 (3)	0.017 (3)	0.014 (2)
C19	0.077 (3)	0.047 (2)	0.052 (3)	0.029 (2)	0.019 (2)	0.020 (2)
C20	0.058 (2)	0.0325 (19)	0.044 (2)	0.0147 (17)	0.0094 (18)	0.0109 (16)
C21	0.062 (3)	0.049 (2)	0.065 (3)	0.009 (2)	0.000 (2)	0.010 (2)
C22	0.063 (3)	0.074 (3)	0.102 (4)	0.007 (3)	−0.009 (3)	0.022 (3)
C23	0.061 (3)	0.092 (4)	0.135 (5)	0.022 (3)	0.020 (3)	0.047 (4)
C24	0.088 (4)	0.081 (3)	0.095 (4)	0.040 (3)	0.049 (3)	0.043 (3)
C25	0.060 (2)	0.048 (2)	0.055 (2)	0.0086 (19)	0.0147 (19)	0.0227 (19)
C26	0.071 (3)	0.055 (2)	0.052 (2)	−0.001 (2)	0.015 (2)	0.022 (2)
C27	0.054 (2)	0.045 (2)	0.061 (2)	0.0096 (19)	0.0161 (19)	0.0212 (19)
C28	0.052 (3)	0.114 (4)	0.106 (4)	0.012 (3)	0.039 (3)	0.042 (3)
C29	0.061 (2)	0.035 (2)	0.066 (3)	0.0124 (18)	0.022 (2)	0.0186 (19)
C30	0.062 (3)	0.047 (2)	0.065 (3)	−0.001 (2)	0.017 (2)	0.021 (2)
C31	0.050 (2)	0.038 (2)	0.059 (2)	0.0021 (18)	0.0131 (19)	0.0160 (18)
C32	0.047 (2)	0.068 (3)	0.097 (3)	0.014 (2)	0.023 (2)	0.025 (2)
Cu1	0.0421 (3)	0.0321 (2)	0.0417 (3)	0.00717 (17)	0.00974 (18)	0.00997 (18)
N1	0.0499 (18)	0.0345 (15)	0.0460 (17)	0.0054 (14)	0.0122 (14)	0.0116 (13)
N2	0.0433 (17)	0.0325 (15)	0.0437 (17)	0.0034 (13)	0.0083 (13)	0.0089 (13)
N3	0.0475 (18)	0.0539 (19)	0.0560 (19)	0.0007 (16)	0.0189 (15)	0.0150 (16)
N4	0.0430 (17)	0.0433 (17)	0.0508 (18)	0.0046 (14)	0.0133 (14)	0.0118 (14)
O1	0.0524 (15)	0.0514 (15)	0.0562 (16)	0.0112 (12)	0.0009 (12)	0.0111 (13)
O2	0.0456 (14)	0.0348 (13)	0.0479 (15)	0.0066 (11)	0.0114 (11)	0.0092 (11)
O3	0.0512 (14)	0.0351 (13)	0.0468 (15)	0.0091 (11)	0.0119 (11)	0.0113 (11)
O4	0.0604 (16)	0.0506 (15)	0.0530 (16)	0.0123 (13)	0.0076 (13)	0.0177 (13)
O1W	0.091 (2)	0.085 (2)	0.0606 (18)	0.0234 (17)	−0.0078 (15)	0.0132 (15)

Geometric parameters (Å, º) top

C1—O1	1.233 (4)	C19—C20	1.423 (5)
C1—O2	1.280 (4)	C20—C21	1.416 (5)
C1—C2	1.519 (4)	C21—C22	1.343 (5)
C2—C3	1.528 (4)	C21—H21	0.9300
C2—H2A	0.9700	C22—C23	1.396 (6)
C2—H2B	0.9700	C22—H22	0.9300
C3—C4	1.355 (4)	C23—C24	1.351 (6)
C3—C8	1.419 (4)	C23—H23	0.9300
C4—C5	1.408 (5)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.331 (4)
C5—C6	1.360 (5)	C25—N1	1.369 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.403 (5)	C26—N3	1.360 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C12	1.404 (5)	C27—N1	1.319 (4)
C7—C8	1.438 (4)	C27—N3	1.341 (4)
C8—C9	1.413 (4)	C27—H27	0.9300
C9—C10	1.353 (4)	C28—N3	1.460 (4)
C9—H9	0.9300	C28—H28A	0.9600
C10—C11	1.385 (5)	C28—H28B	0.9600
C10—H10	0.9300	C28—H28C	0.9600
C11—C12	1.345 (5)	C29—C30	1.338 (4)
C11—H11	0.9300	C29—N2	1.377 (4)
C12—H12	0.9300	C29—H29	0.9300
C13—O4	1.226 (4)	C30—N4	1.356 (4)
C13—O3	1.288 (4)	C30—H30	0.9300
C13—C14	1.525 (4)	C31—N2	1.319 (4)
C14—C15	1.517 (4)	C31—N4	1.334 (4)
C14—H14A	0.9700	C31—H31	0.9300
C14—H14B	0.9700	C32—N4	1.463 (4)
C15—C16	1.356 (5)	C32—H32A	0.9600
C15—C20	1.421 (5)	C32—H32B	0.9600
C16—C17	1.406 (5)	C32—H32C	0.9600
C16—H16	0.9300	Cu1—O2	1.969 (2)
C17—C18	1.348 (6)	Cu1—O3	1.974 (2)
C17—H17	0.9300	Cu1—N1	1.981 (3)
C18—C19	1.415 (5)	Cu1—N2	1.985 (3)
C18—H18	0.9300	O1W—H1WA	0.8500
C19—C24	1.413 (6)	O1W—H1WB	0.8501

O1—C1—O2	122.5 (3)	C15—C20—C19	118.9 (3)
O1—C1—C2	120.6 (3)	C22—C21—C20	122.0 (4)
O2—C1—C2	116.9 (3)	C22—C21—H21	119.0
C1—C2—C3	111.2 (3)	C20—C21—H21	119.0
C1—C2—H2A	109.4	C21—C22—C23	120.5 (5)
C3—C2—H2A	109.4	C21—C22—H22	119.8
C1—C2—H2B	109.4	C23—C22—H22	119.8
C3—C2—H2B	109.4	C24—C23—C22	120.3 (5)
H2A—C2—H2B	108.0	C24—C23—H23	119.9
C4—C3—C8	120.3 (3)	C22—C23—H23	119.9
C4—C3—C2	119.8 (3)	C23—C24—C19	121.0 (4)
C8—C3—C2	119.8 (3)	C23—C24—H24	119.5
C3—C4—C5	121.9 (3)	C19—C24—H24	119.5
C3—C4—H4	119.1	C26—C25—N1	110.2 (3)
C5—C4—H4	119.1	C26—C25—H25	125.0
C6—C5—C4	119.6 (4)	N1—C25—H25	124.8
C6—C5—H5	120.2	C25—C26—N3	106.7 (3)
C4—C5—H5	120.2	C25—C26—H26	126.6
C5—C6—C7	120.7 (4)	N3—C26—H26	126.7
C5—C6—H6	119.7	N1—C27—N3	111.1 (3)
C7—C6—H6	119.7	N1—C27—H27	124.5
C6—C7—C12	122.1 (3)	N3—C27—H27	124.4
C6—C7—C8	119.9 (3)	N3—C28—H28A	109.5
C12—C7—C8	118.0 (4)	N3—C28—H28B	109.5
C9—C8—C3	124.6 (3)	H28A—C28—H28B	109.5
C9—C8—C7	117.8 (3)	N3—C28—H28C	109.5
C3—C8—C7	117.6 (3)	H28A—C28—H28C	109.5
C10—C9—C8	121.4 (3)	H28B—C28—H28C	109.5
C10—C9—H9	119.3	C30—C29—N2	109.5 (3)
C8—C9—H9	119.3	C30—C29—H29	125.2
C9—C10—C11	120.3 (4)	N2—C29—H29	125.2
C9—C10—H10	119.8	C29—C30—N4	107.0 (3)
C11—C10—H10	119.8	C29—C30—H30	126.6
C12—C11—C10	120.8 (4)	N4—C30—H30	126.4
C12—C11—H11	119.6	N2—C31—N4	111.6 (3)
C10—C11—H11	119.6	N2—C31—H31	124.2
C11—C12—C7	121.7 (4)	N4—C31—H31	124.1
C11—C12—H12	119.1	N4—C32—H32A	109.5
C7—C12—H12	119.1	N4—C32—H32B	109.5
O4—C13—O3	123.2 (3)	H32A—C32—H32B	109.5
O4—C13—C14	120.0 (3)	N4—C32—H32C	109.5
O3—C13—C14	116.7 (3)	H32A—C32—H32C	109.5
C15—C14—C13	112.8 (3)	H32B—C32—H32C	109.5
C15—C14—H14A	109.0	O2—Cu1—O3	170.52 (10)
C13—C14—H14A	109.0	O2—Cu1—N1	88.15 (10)
C15—C14—H14B	109.0	O3—Cu1—N1	92.02 (10)
C13—C14—H14B	109.0	O2—Cu1—N2	89.41 (9)
H14A—C14—H14B	107.8	O3—Cu1—N2	91.82 (9)
C16—C15—C20	120.1 (3)	N1—Cu1—N2	170.95 (11)
C16—C15—C14	119.5 (3)	C27—N1—C25	105.1 (3)
C20—C15—C14	120.5 (3)	C27—N1—Cu1	128.9 (2)
C15—C16—C17	121.1 (4)	C25—N1—Cu1	126.0 (2)
C15—C16—H16	119.4	C31—N2—C29	104.9 (3)
C17—C16—H16	119.4	C31—N2—Cu1	126.5 (2)
C18—C17—C16	120.2 (4)	C29—N2—Cu1	128.7 (2)
C18—C17—H17	119.9	C27—N3—C26	107.0 (3)
C16—C17—H17	119.9	C27—N3—C28	126.8 (3)
C17—C18—C19	121.2 (4)	C26—N3—C28	126.2 (3)
C17—C18—H18	119.4	C31—N4—C30	107.0 (3)
C19—C18—H18	119.4	C31—N4—C32	126.9 (3)
C24—C19—C18	122.4 (4)	C30—N4—C32	126.1 (3)
C24—C19—C20	119.1 (4)	C1—O2—Cu1	106.53 (19)
C18—C19—C20	118.5 (4)	C13—O3—Cu1	108.00 (19)
C21—C20—C15	123.9 (3)	H1WA—O1W—H1WB	107.7
C21—C20—C19	117.3 (4)

O1—C1—C2—C3	89.1 (4)	C20—C21—C22—C23	−0.9 (6)
O2—C1—C2—C3	−89.1 (4)	C21—C22—C23—C24	1.5 (7)
C1—C2—C3—C4	−97.6 (4)	C22—C23—C24—C19	−1.2 (7)
C1—C2—C3—C8	80.5 (4)	C18—C19—C24—C23	178.5 (4)
C8—C3—C4—C5	0.3 (5)	C20—C19—C24—C23	0.4 (6)
C2—C3—C4—C5	178.4 (3)	N1—C25—C26—N3	0.1 (4)
C3—C4—C5—C6	−1.0 (5)	N2—C29—C30—N4	−0.6 (4)
C4—C5—C6—C7	1.0 (5)	N3—C27—N1—C25	−0.2 (4)
C5—C6—C7—C12	−179.4 (3)	N3—C27—N1—Cu1	−179.4 (2)
C5—C6—C7—C8	−0.4 (5)	C26—C25—N1—C27	0.1 (4)
C4—C3—C8—C9	179.7 (3)	C26—C25—N1—Cu1	179.3 (2)
C2—C3—C8—C9	1.5 (5)	O2—Cu1—N1—C27	−153.0 (3)
C4—C3—C8—C7	0.3 (5)	O3—Cu1—N1—C27	17.5 (3)
C2—C3—C8—C7	−177.9 (3)	N2—Cu1—N1—C27	132.6 (6)
C6—C7—C8—C9	−179.7 (3)	O2—Cu1—N1—C25	27.9 (3)
C12—C7—C8—C9	−0.7 (4)	O3—Cu1—N1—C25	−161.5 (3)
C6—C7—C8—C3	−0.2 (4)	N2—Cu1—N1—C25	−46.5 (8)
C12—C7—C8—C3	178.8 (3)	N4—C31—N2—C29	−0.6 (4)
C3—C8—C9—C10	−178.0 (3)	N4—C31—N2—Cu1	180.0 (2)
C7—C8—C9—C10	1.4 (5)	C30—C29—N2—C31	0.7 (4)
C8—C9—C10—C11	−1.3 (5)	C30—C29—N2—Cu1	−179.8 (2)
C9—C10—C11—C12	0.5 (6)	O2—Cu1—N2—C31	−12.6 (3)
C10—C11—C12—C7	0.2 (6)	O3—Cu1—N2—C31	176.8 (3)
C6—C7—C12—C11	178.9 (4)	N1—Cu1—N2—C31	61.7 (8)
C8—C7—C12—C11	−0.1 (5)	O2—Cu1—N2—C29	168.0 (3)
O4—C13—C14—C15	−55.1 (4)	O3—Cu1—N2—C29	−2.6 (3)
O3—C13—C14—C15	125.9 (3)	N1—Cu1—N2—C29	−117.6 (7)
C13—C14—C15—C16	98.1 (4)	N1—C27—N3—C26	0.2 (4)
C13—C14—C15—C20	−81.3 (4)	N1—C27—N3—C28	−179.1 (3)
C20—C15—C16—C17	1.3 (5)	C25—C26—N3—C27	−0.1 (4)
C14—C15—C16—C17	−178.1 (3)	C25—C26—N3—C28	179.2 (4)
C15—C16—C17—C18	0.4 (6)	N2—C31—N4—C30	0.2 (4)
C16—C17—C18—C19	−0.9 (6)	N2—C31—N4—C32	−177.6 (3)
C17—C18—C19—C24	−178.3 (4)	C29—C30—N4—C31	0.3 (4)
C17—C18—C19—C20	−0.2 (5)	C29—C30—N4—C32	178.0 (3)
C16—C15—C20—C21	177.5 (3)	O1—C1—O2—Cu1	2.0 (3)
C14—C15—C20—C21	−3.1 (5)	C2—C1—O2—Cu1	−179.8 (2)
C16—C15—C20—C19	−2.4 (5)	O3—Cu1—O2—C1	3.1 (6)
C14—C15—C20—C19	177.0 (3)	N1—Cu1—O2—C1	94.28 (19)
C24—C19—C20—C21	0.1 (5)	N2—Cu1—O2—C1	−94.44 (19)
C18—C19—C20—C21	−178.0 (3)	O4—C13—O3—Cu1	−1.0 (4)
C24—C19—C20—C15	−179.9 (3)	C14—C13—O3—Cu1	178.0 (2)
C18—C19—C20—C15	1.9 (5)	O2—Cu1—O3—C13	176.3 (5)
C15—C20—C21—C22	−179.8 (3)	N1—Cu1—O3—C13	85.4 (2)
C19—C20—C21—C22	0.1 (5)	N2—Cu1—O3—C13	−86.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.85	1.97	2.789 (3)	163
O1W—H1WB···O3ⁱ	0.85	2.07	2.904 (3)	167

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₉O₂)₂(C₄H₆N₂)₂]·H₂O
M_r	616.16
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7213 (10), 12.8689 (14), 13.5787 (15)
α, β, γ (°)	107.223 (1), 90.295 (2), 90.931 (1)
V (Å³)	1455.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.843, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	11175, 5094, 3534
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.102, 1.03
No. of reflections	5094
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.31

Computer programs: APEX2 (Bruker 2007), SAINT (Bruker 2007), SAINT'(Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1	0.85	1.97	2.789 (3)	163
O1W—H1WB···O3ⁱ	0.85	2.07	2.904 (3)	167

Symmetry code: (i) −x+1, −y+2, −z+1.

References

Boiani, M. & Gonzales, M. (2005). Mini Rev. Med. Chem. 5, 409–424. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L.-F., Zhang, J., Song, L.-J., Wang, W.-G. & Ju, Z.-F. (2004). Acta Cryst. E60, m1032–m1034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ji, L.-L., Liu, J.-S. & Song, W.-D. (2011). Acta Cryst. E67, m606. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parshina, L. N. & Trofimov, B. A. (2011). Russ. Chem. Bull. 60, 601–614. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, D.-X., Feng, L.-X. & Zhang, X.-Q. (2006). Chin. J. Inorg. Chem. 22, 1891–1894. CAS Google Scholar
Yang, Y.-Q., Li, C.-H. L. W. & Kuang, Y.-F. (2008). Chin. J. Struct. Chem. 30, 4524–4530. Google Scholar
Yin, F.-J., Zhao, H. & Hu, X.-L. (2010). Synth. React. Inorg. Met. Org. Nano-Metal Chem. 40, 606–612. CAS Google Scholar

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Volume 67| Part 12| December 2011| Page m1821

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