Aqua­(2-oxido-2,2-diphenyl­acetato-κ2O1,O2)(1,10-phenanthroline-κ2N,N′)copper(II)

Yang, X.-X.; Zhang, F.-Y.; Xu, S.-H.

doi:10.1107/S1600536809053483

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m69

doi:10.1107/S1600536809053483

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Aqua(2-oxido-2,2-diphenylacetato-κ²O¹,O²)(1,10-phenanthroline-κ²N,N′)copper(II)

Xiao-Xia Yang,^a Fu-Yong Zhang ^a and Shi-Hai Xu ^a ^*

^aDepartment of Chemistry, Jinan University, Guangzhou 510632, People's Republic of China
^*Correspondence e-mail: xuhs09@126.com

(Received 6 December 2009; accepted 11 December 2009; online 16 December 2009)

In the title mononuclear complex, [Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)], the Cu^II atom is five-coordinated by two N atoms from a 1,10-phenanthroline (phen) ligand, two O atoms from a benzilate ligand and one O atom from a water molecule in a distorted square-pyramidal geometry. The crystal structure is stabilized via intermolecular O—H⋯O and C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π stacking interactions between the pyridine and benzene rings of neighboring phen ligands [centroid–centroid distances = 3.684 (2), 3.564 (2) and 3.380 (1) Å].

Related literature

For related structures of benzilate compounds, see: Mora et al. (2003 ); Rojas et al. (2003 ).

Experimental

Crystal data

[Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)]
M_r = 487.98
Triclinic, $[P \overline 1]$
a = 7.4473 (15) Å
b = 9.757 (2) Å
c = 15.319 (3) Å
α = 102.99 (3)°
β = 98.39 (3)°
γ = 96.70 (3)°
V = 1060.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.07 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.740, T_max = 0.807
8229 measured reflections
3802 independent reflections
2607 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.229
S = 1.09
3802 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −1.54 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.949 (4)
Cu1—O3	1.853 (4)
Cu1—N1	2.014 (4)
Cu1—N2	2.019 (5)
Cu1—O1W	2.476 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2ⁱ	0.82	2.07	2.883 (6)	171
O1W—H2W⋯O1ⁱⁱ	0.83	2.13	2.954 (4)	175
C17—H17⋯O1ⁱⁱⁱ	0.93	2.41	3.312 (8)	162
C21—H21⋯Cg1ⁱ	0.93	2.46	3.267 (8)	146
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z; (iii) x-1, y-1, z. Cg1 is the centroid of the C9–C14 ring.

Data collection: CrystalStructure (Rigaku/MSC, 2002 ); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053483/hy2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053483/hy2263Isup2.hkl

checkCIF report

Comment top

In the structural investigations of benzilate complexes, it has been found that the benzilic acid functions as a multidentate ligand with versatile binding and coordination modes (Mora et al., 2003; Rojas et al., 2003). In this paper, we report the structure of the title compound, a copper(II) complex obtained by the reaction of benzilic acid, 1,10-phenanthroline (phen) and copper chloride in an alkaline aqueous solution.

As depicted in Fig. 1, the Cu^II atom exists in a square-pyramidal environment, defined by two O atoms from one benzilate ligand, two N atoms from one phen ligand and one water molecule. The crystal structure is stabilized via intermolecular O—H···O and C—H···O hydrogen bonds, C—H···π interactions (Table 1) and π–π stacking interactions between the pyridine and benzene rings of neighboring phen ligands (Fig. 2), with the centroid–centroid distances of Cg2···Cg3ⁱ = 3.684 (2), Cg3···Cg4ⁱ = 3.564 (2) and Cg4···Cg4ⁱⁱ = 3.380 (1) Å [Cg2, Cg3 and Cg4 are the centroids of the N1, C15, C16, C17, C23, C25 ring, the N2, C20, C21, C22, C24, C26 ring and the C18, C19, C23, C24, C25, C26 ring, respectively. Symmetry codes: (i) -x, -y, -z; (ii) -1-x, -y, -z].

Related literature top

For related structures of benzilate compounds, see: Mora et al. (2003); Rojas et al. (2003).

Experimental top

A mixture of copper chloride (0.134 g, 1 mmol), benzilic acid (0.228 g, 1 mmol), phen (0.18 g, 1 mmol), NaOH (0.06 g, 1.5 mmol), EtOH (6 ml) and H₂O (6 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 358 K for 8 h and then cooled to room temperature at a rate of 10 K h^-1. The blue crystals obtained were washed with water and dried in air.

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2002); cell refinement: CrystalStructure (Rigaku/MSC, 2002); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. A packing view of the title compound. C—H···π interactions and π–π stacking interactions are shown as dashed lines.

Aqua(2-oxido-2,2-diphenylacetato-κ²O¹,O²)(1,10- phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)]	Z = 2
M_r = 487.98	F(000) = 502
Triclinic, P1	D_x = 1.529 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4473 (15) Å	Cell parameters from 2895 reflections
b = 9.757 (2) Å	θ = 2.4–27.9°
c = 15.319 (3) Å	µ = 1.07 mm⁻¹
α = 102.99 (3)°	T = 293 K
β = 98.39 (3)°	Block, blue
γ = 96.70 (3)°	0.30 × 0.26 × 0.21 mm
V = 1060.1 (4) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3802 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 25.2°, θ_min = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −8→8
T_min = 0.740, T_max = 0.807	k = −11→11
8229 measured reflections	l = −18→18

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1409P)²] where P = (F_o² + 2F_c²)/3
3802 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −1.54 e Å⁻³

Crystal data top

[Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)]	γ = 96.70 (3)°
M_r = 487.98	V = 1060.1 (4) Å³
Triclinic, P1	Z = 2
a = 7.4473 (15) Å	Mo Kα radiation
b = 9.757 (2) Å	µ = 1.07 mm⁻¹
c = 15.319 (3) Å	T = 293 K
α = 102.99 (3)°	0.30 × 0.26 × 0.21 mm
β = 98.39 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3802 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2607 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.807	R_int = 0.049
8229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.229	H-atom parameters constrained
S = 1.09	Δρ_max = 0.73 e Å⁻³
3802 reflections	Δρ_min = −1.54 e Å⁻³
298 parameters

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

	x	y	z	U_iso*/U_eq
Cu1	−0.01419 (8)	0.32886 (6)	0.11584 (5)	0.0478 (3)
O1	0.4514 (5)	0.5892 (4)	0.1612 (3)	0.0550 (10)
O2	0.1851 (5)	0.4550 (4)	0.0914 (3)	0.0480 (9)
O3	0.0740 (5)	0.4170 (4)	0.2375 (3)	0.0536 (10)
N1	−0.1600 (6)	0.1655 (5)	0.1476 (4)	0.0507 (12)
N2	−0.0958 (6)	0.2006 (5)	−0.0106 (3)	0.0471 (11)
C1	0.3024 (7)	0.5192 (5)	0.1632 (4)	0.0430 (12)
C2	0.2428 (7)	0.5060 (6)	0.2553 (4)	0.0458 (13)
C3	0.3883 (8)	0.4467 (5)	0.3150 (4)	0.0505 (13)
C4	0.3222 (9)	0.3619 (7)	0.3695 (5)	0.0617 (16)
H4	0.1962	0.3390	0.3661	0.074*
C5	0.4417 (11)	0.3116 (7)	0.4283 (5)	0.072 (2)
H5	0.3951	0.2549	0.4637	0.087*
C6	0.6278 (11)	0.3443 (7)	0.4350 (5)	0.0717 (19)
H6	0.7076	0.3104	0.4748	0.086*
C7	0.6948 (10)	0.4270 (8)	0.3826 (5)	0.0727 (19)
H7	0.8211	0.4506	0.3874	0.087*
C8	0.5765 (8)	0.4766 (7)	0.3222 (5)	0.0595 (16)
H8	0.6249	0.5309	0.2860	0.071*
C9	0.2267 (8)	0.6559 (6)	0.3114 (4)	0.0481 (13)
C10	0.3750 (8)	0.7666 (6)	0.3423 (4)	0.0532 (14)
H10	0.4902	0.7518	0.3289	0.064*
C11	0.3524 (10)	0.8971 (7)	0.3922 (5)	0.0641 (17)
H11	0.4519	0.9704	0.4108	0.077*
C12	0.1844 (10)	0.9215 (7)	0.4153 (5)	0.0704 (18)
H12	0.1710	1.0092	0.4509	0.085*
C13	0.0366 (11)	0.8128 (8)	0.3845 (5)	0.079 (2)
H13	−0.0778	0.8279	0.3990	0.095*
C14	0.0569 (9)	0.6817 (7)	0.3324 (5)	0.0633 (17)
H14	−0.0444	0.6103	0.3113	0.076*
C15	−0.1857 (8)	0.1530 (7)	0.2300 (5)	0.0600 (16)
H15	−0.1392	0.2287	0.2802	0.072*
C16	−0.2811 (9)	0.0283 (8)	0.2425 (6)	0.0707 (19)
H16	−0.2958	0.0222	0.3009	0.085*
C17	−0.3527 (9)	−0.0840 (7)	0.1704 (6)	0.068 (2)
H17	−0.4187	−0.1656	0.1788	0.081*
C18	−0.3932 (8)	−0.1834 (6)	0.0027 (6)	0.0660 (19)
H18	−0.4590	−0.2681	0.0068	0.079*
C19	−0.3644 (8)	−0.1664 (6)	−0.0801 (6)	0.070 (2)
H19	−0.4125	−0.2393	−0.1318	0.085*
C20	−0.2216 (8)	−0.0133 (7)	−0.1706 (5)	0.0630 (17)
H20	−0.2624	−0.0833	−0.2245	0.076*
C21	−0.1223 (8)	0.1146 (7)	−0.1719 (5)	0.0626 (16)
H21	−0.0952	0.1311	−0.2264	0.075*
C22	−0.0627 (8)	0.2192 (6)	−0.0902 (4)	0.0540 (15)
H22	0.0030	0.3054	−0.0918	0.065*
C23	−0.3250 (7)	−0.0746 (6)	0.0826 (5)	0.0572 (17)
C24	−0.2607 (8)	−0.0375 (6)	−0.0896 (5)	0.0545 (15)
C25	−0.2280 (6)	0.0541 (5)	0.0764 (5)	0.0481 (14)
C26	−0.1937 (7)	0.0717 (5)	−0.0108 (4)	0.0486 (14)
O1W	−0.2525 (6)	0.4712 (4)	0.0741 (3)	0.0641 (12)
H1W	−0.2344	0.5019	0.0299	0.096*
H2W	−0.3373	0.5069	0.0958	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0511 (4)	0.0331 (4)	0.0568 (5)	0.0027 (3)	0.0079 (3)	0.0093 (3)
O1	0.051 (2)	0.052 (2)	0.062 (3)	−0.0036 (18)	0.013 (2)	0.018 (2)
O2	0.052 (2)	0.042 (2)	0.048 (2)	0.0046 (17)	0.0058 (18)	0.0105 (18)
O3	0.055 (2)	0.047 (2)	0.052 (3)	−0.0086 (18)	0.0080 (19)	0.0090 (19)
N1	0.048 (2)	0.036 (2)	0.069 (3)	0.006 (2)	0.014 (2)	0.012 (2)
N2	0.047 (2)	0.038 (2)	0.059 (3)	0.0138 (19)	0.009 (2)	0.014 (2)
C1	0.057 (3)	0.030 (3)	0.046 (3)	0.011 (2)	0.013 (3)	0.013 (2)
C2	0.044 (3)	0.038 (3)	0.055 (4)	0.003 (2)	0.011 (3)	0.012 (3)
C3	0.069 (3)	0.032 (3)	0.052 (3)	0.009 (2)	0.016 (3)	0.008 (2)
C4	0.070 (4)	0.050 (3)	0.066 (4)	0.001 (3)	0.012 (3)	0.020 (3)
C5	0.103 (5)	0.050 (4)	0.071 (5)	0.011 (4)	0.011 (4)	0.033 (4)
C6	0.092 (5)	0.060 (4)	0.070 (5)	0.033 (4)	0.005 (4)	0.023 (4)
C7	0.074 (4)	0.071 (5)	0.081 (5)	0.032 (4)	0.016 (4)	0.023 (4)
C8	0.059 (3)	0.058 (4)	0.069 (4)	0.017 (3)	0.015 (3)	0.024 (3)
C9	0.057 (3)	0.039 (3)	0.048 (3)	0.008 (2)	0.008 (3)	0.012 (3)
C10	0.058 (3)	0.042 (3)	0.055 (4)	0.000 (3)	0.002 (3)	0.011 (3)
C11	0.084 (4)	0.042 (3)	0.055 (4)	0.002 (3)	−0.005 (3)	0.002 (3)
C12	0.092 (5)	0.044 (4)	0.069 (5)	0.012 (4)	0.014 (4)	0.002 (3)
C13	0.094 (5)	0.076 (5)	0.080 (5)	0.042 (4)	0.036 (4)	0.019 (4)
C14	0.063 (4)	0.051 (4)	0.076 (5)	0.004 (3)	0.020 (3)	0.013 (3)
C15	0.061 (3)	0.046 (3)	0.074 (5)	0.003 (3)	0.017 (3)	0.014 (3)
C16	0.069 (4)	0.067 (4)	0.087 (5)	0.012 (3)	0.027 (4)	0.031 (4)
C17	0.055 (3)	0.049 (4)	0.110 (6)	0.009 (3)	0.022 (4)	0.037 (4)
C18	0.053 (3)	0.031 (3)	0.108 (6)	0.005 (3)	0.003 (4)	0.013 (4)
C19	0.054 (3)	0.033 (3)	0.107 (6)	0.012 (3)	−0.016 (4)	−0.004 (4)
C20	0.058 (3)	0.051 (4)	0.067 (5)	0.020 (3)	−0.008 (3)	−0.005 (3)
C21	0.063 (4)	0.059 (4)	0.064 (4)	0.024 (3)	0.000 (3)	0.012 (3)
C22	0.051 (3)	0.050 (3)	0.065 (4)	0.016 (3)	0.008 (3)	0.020 (3)
C23	0.038 (3)	0.038 (3)	0.097 (5)	0.011 (2)	0.011 (3)	0.018 (3)
C24	0.046 (3)	0.043 (3)	0.068 (4)	0.015 (2)	−0.005 (3)	0.006 (3)
C25	0.032 (2)	0.032 (3)	0.079 (4)	0.006 (2)	0.008 (3)	0.012 (3)
C26	0.043 (3)	0.032 (3)	0.068 (4)	0.014 (2)	0.000 (3)	0.008 (3)
O1W	0.067 (2)	0.062 (3)	0.072 (3)	0.021 (2)	0.019 (2)	0.026 (2)

Geometric parameters (Å, º) top

Cu1—O2	1.949 (4)	C11—C12	1.381 (10)
Cu1—O3	1.853 (4)	C11—H11	0.9300
Cu1—N1	2.014 (4)	C12—C13	1.382 (10)
Cu1—N2	2.019 (5)	C12—H12	0.9300
Cu1—O1W	2.476 (5)	C13—C14	1.385 (10)
O1—C1	1.241 (6)	C13—H13	0.9300
O2—C1	1.283 (7)	C14—H14	0.9300
O3—C2	1.396 (6)	C15—C16	1.402 (9)
N1—C15	1.333 (8)	C15—H15	0.9300
N1—C25	1.343 (8)	C16—C17	1.361 (10)
N2—C22	1.325 (8)	C16—H16	0.9300
N2—C26	1.377 (7)	C17—C23	1.411 (10)
C1—C2	1.567 (7)	C17—H17	0.9300
C2—C9	1.548 (8)	C18—C19	1.360 (10)
C2—C3	1.562 (8)	C18—C23	1.411 (10)
C3—C8	1.381 (8)	C18—H18	0.9300
C3—C4	1.400 (8)	C19—C24	1.445 (9)
C4—C5	1.382 (10)	C19—H19	0.9300
C4—H4	0.9300	C20—C24	1.379 (9)
C5—C6	1.369 (10)	C20—C21	1.380 (9)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.363 (10)	C21—C22	1.402 (9)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.389 (9)	C22—H22	0.9300
C7—H7	0.9300	C23—C25	1.403 (7)
C8—H8	0.9300	C24—C26	1.401 (9)
C9—C14	1.387 (8)	C25—C26	1.441 (9)
C9—C10	1.397 (8)	O1W—H1W	0.8214
C10—C11	1.373 (9)	O1W—H2W	0.8307
C10—H10	0.9300

O3—Cu1—O2	85.53 (16)	C9—C10—H10	119.7
O3—Cu1—N1	91.89 (19)	C10—C11—C12	121.2 (6)
O2—Cu1—N1	163.11 (17)	C10—C11—H11	119.4
O3—Cu1—N2	169.49 (17)	C12—C11—H11	119.4
O2—Cu1—N2	98.71 (17)	C11—C12—C13	118.6 (6)
N1—Cu1—N2	81.2 (2)	C11—C12—H12	120.7
N1—Cu1—O1W	102.84 (17)	C13—C12—H12	120.7
N2—Cu1—O1W	86.73 (17)	C12—C13—C14	120.7 (7)
O2—Cu1—O1W	93.99 (16)	C12—C13—H13	119.7
O3—Cu1—O1W	102.66 (16)	C14—C13—H13	119.7
C1—O2—Cu1	113.1 (3)	C13—C14—C9	120.7 (6)
C2—O3—Cu1	115.2 (3)	C13—C14—H14	119.6
C15—N1—C25	117.9 (5)	C9—C14—H14	119.6
C15—N1—Cu1	127.8 (4)	N1—C15—C16	121.5 (7)
C25—N1—Cu1	114.2 (4)	N1—C15—H15	119.2
C22—N2—C26	116.9 (5)	C16—C15—H15	119.2
C22—N2—Cu1	130.3 (4)	C17—C16—C15	120.8 (7)
C26—N2—Cu1	112.7 (4)	C17—C16—H16	119.6
O1—C1—O2	123.3 (5)	C15—C16—H16	119.6
O1—C1—C2	121.6 (5)	C16—C17—C23	118.9 (6)
O2—C1—C2	115.1 (4)	C16—C17—H17	120.6
O3—C2—C9	110.0 (4)	C23—C17—H17	120.6
O3—C2—C3	109.6 (4)	C19—C18—C23	121.1 (6)
C9—C2—C3	106.6 (5)	C19—C18—H18	119.5
O3—C2—C1	109.5 (5)	C23—C18—H18	119.5
C9—C2—C1	109.1 (4)	C18—C19—C24	121.4 (6)
C3—C2—C1	112.0 (4)	C18—C19—H19	119.3
C8—C3—C4	117.2 (6)	C24—C19—H19	119.3
C8—C3—C2	125.7 (5)	C24—C20—C21	120.1 (6)
C4—C3—C2	117.0 (5)	C24—C20—H20	119.9
C5—C4—C3	120.9 (6)	C21—C20—H20	119.9
C5—C4—H4	119.5	C20—C21—C22	119.2 (6)
C3—C4—H4	119.5	C20—C21—H21	120.4
C6—C5—C4	120.7 (6)	C22—C21—H21	120.4
C6—C5—H5	119.6	N2—C22—C21	122.8 (6)
C4—C5—H5	119.6	N2—C22—H22	118.6
C7—C6—C5	119.2 (7)	C21—C22—H22	118.6
C7—C6—H6	120.4	C25—C23—C17	116.4 (6)
C5—C6—H6	120.4	C25—C23—C18	119.5 (7)
C6—C7—C8	120.7 (7)	C17—C23—C18	124.1 (6)
C6—C7—H7	119.6	C20—C24—C26	117.0 (6)
C8—C7—H7	119.6	C20—C24—C19	125.0 (6)
C3—C8—C7	121.2 (6)	C26—C24—C19	118.0 (6)
C3—C8—H8	119.4	N1—C25—C23	124.5 (6)
C7—C8—H8	119.4	N1—C25—C26	115.8 (5)
C14—C9—C10	118.2 (6)	C23—C25—C26	119.7 (6)
C14—C9—C2	118.6 (5)	N2—C26—C24	123.8 (6)
C10—C9—C2	123.2 (5)	N2—C26—C25	115.9 (5)
C11—C10—C9	120.6 (6)	C24—C26—C25	120.3 (5)
C11—C10—H10	119.7	H1W—O1W—H2W	109.4

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱ	0.82	2.07	2.883 (6)	171
O1W—H2W···O1ⁱⁱ	0.83	2.13	2.954 (4)	175
C17—H17···O1ⁱⁱⁱ	0.93	2.41	3.312 (8)	162
C21—H21···Cg1ⁱ	0.93	2.46	3.267 (8)	146

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z; (iii) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₁₀O₃)(C₁₂H₈N₂)(H₂O)]
M_r	487.98
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4473 (15), 9.757 (2), 15.319 (3)
α, β, γ (°)	102.99 (3), 98.39 (3), 96.70 (3)
V (Å³)	1060.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.30 × 0.26 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.740, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	8229, 3802, 2607
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.229, 1.09
No. of reflections	3802
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −1.54

Computer programs: CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O2	1.949 (4)	Cu1—N2	2.019 (5)
Cu1—O3	1.853 (4)	Cu1—O1W	2.476 (5)
Cu1—N1	2.014 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱ	0.82	2.07	2.883 (6)	171
O1W—H2W···O1ⁱⁱ	0.83	2.13	2.954 (4)	175
C17—H17···O1ⁱⁱⁱ	0.93	2.41	3.312 (8)	162
C21—H21···Cg1ⁱ	0.93	2.46	3.267 (8)	146

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z; (iii) x−1, y−1, z.

Acknowledgements

The authors kindly acknowledge the 863 Program of China (2006 A A09Z408) and the National Natural Science Foundation of China (20772048) for supporting this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Mora, A. J., Fitch, A. N., Ramirez, B. M., Delgado, G. E., Brunelli, M. & Wright, J. (2003). Acta Cryst. B59, 378–383. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Rojas, L. S., Ramírez, B. M., Mora, A. J., Delgado, G. E. & Delgado, G. D. (2003). Acta Cryst. E59, m647–m651. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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