Bis(acetato-κO)[1,2-bis­(2-pyridylmeth­oxy)benzene-κ4N,O,O′,N′]copper(II) monohydrate

Zhang, S.; Wang, Y.-J.; Ma, D.-S.; Liu, Y.; Gao, J.-S.

doi:10.1107/S160053681001874X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page m701

https://doi.org/10.1107/S160053681001874X

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Bis(acetato-κO)[1,2-bis(2-pyridylmethoxy)benzene-κ⁴N,O,O′,N′]copper(II) monohydrate

Shuang Zhang,^a Yu-Jie Wang,^a,^b Dong-Sheng Ma,^b Ying Liu ^b and Jin-Sheng Gao ^a,^b ^*

^aEngineering Research Center of Pesticide of Heilongjiang Province, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 18 May 2010; accepted 19 May 2010; online 22 May 2010)

In the title compound, [Cu(CH₃COO)₂(C₁₈H₁₆N₂O₂)]·H₂O, the Cu^II ion is six-coordinated in a typically Jahn–Teller distorted octahedral environment defined by two O and two N atoms from the ligand and two O atoms from acetate anions. A linear chain structure propagating in [010] is built up by intermolecular O—H⋯O hydrogen bonds involving the uncoordinated water molecules.

Related literature

For the synthesis and for general backround to flexible pyridyl-based ligands, see: Liu et al. (2010a ,b ).

Experimental

Crystal data

[Cu(C₂H₃O₂)₂(C₁₈H₁₆N₂O₂)]·H₂O
M_r = 491.98
Monoclinic, P 2₁ /c
a = 11.661 (3) Å
b = 14.689 (6) Å
c = 15.553 (4) Å
β = 123.540 (11)°
V = 2220.5 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 291 K
0.20 × 0.19 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.818, T_max = 0.838
21143 measured reflections
4960 independent reflections
3854 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.089
S = 1.05
4960 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O5	1.9529 (16)
Cu1—O3	1.9571 (16)
Cu1—N1	2.0580 (18)
Cu1—N2	2.0823 (18)
Cu1—O2	2.4719 (15)
Cu1—O1	2.5353 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H71⋯O4ⁱ	0.85	1.92	2.772 (3)	174
O7—H72⋯O5	0.85	2.14	2.986 (2)	178
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (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); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681001874X/ng2778sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001874X/ng2778Isup2.hkl

checkCIF report

Comment top

N-Heterocyclic ligands coordinated with transition metal ions can form a variety of topology structures, including macrocycles, polyhedra and linear and helical polymers. Our group has report three kinds of flexible pyridyl-based ligands in previous reports (Liu et al. 20010a; Liu et al. 20010 b). As a part of our continuing work for bipyridyl aromatic ligands, we report the crystal structure of the title compound here.

1,2-Bis(pyridin-2-ylmethoxy)benzene molecule act as a chelating ligand to coordinate with Cu^II ion forming a discrete strucutre. Two acetate counter ions also coordinate to the center Cu^II ion, resulting the Cu^II ion is six-coordinated in quadrangular bipyramid geometry (Figure 1, Table 1).

A one-dimensional chain structure is built up by intermolecular hydrogen bonds involving the uncoordinated water molecules (Figure 2, Table 2).

Related literature top

For the synthesis and for general backround to flexible pyridyl-based ligands, see: Liu et al. (2010a,b).

Experimental top

The 1,2-Bis(pyridin-2-ylmethoxy)benzene was synthesized by the reaction of ο-dihydroxybenzene and 2-chloromethylpyridine hydrochloride under nitrogen atmosphere and alkaline condition (Liu et al., 2010a). Title ligand (0.58 g, 2 mmol) and Cu(CH₃COO)₂.H₂O (0.40 g, 2 mmol) were dissolved in 15 mL e thanol, and then the mixture keep stirring for 30 minute. The resulting solution was filtered, and the filtrate was allowed to stand in a desiccator at room temperature for several days. Bule needle crystals were obtained with yield 34 %.

Structure description top

A one-dimensional chain structure is built up by intermolecular hydrogen bonds involving the uncoordinated water molecules (Figure 2, Table 2).

For the synthesis and for general backround to flexible pyridyl-based ligands, see: Liu et al. (2010a,b).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing the one-dimensional hydrogen bonding structure. Dashed lines indicate the hydrogen bonds, no involving H atoms have been omitted.

Bis(acetato-κO)[1,2-bis(2-pyridylmethoxy)benzene- κ⁴N,O,O',N']copper(II) monohydrate top

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₈H₁₆N₂O₂)]·H₂O	F(000) = 1020
M_r = 491.98	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15798 reflections
a = 11.661 (3) Å	θ = 3.0–27.5°
b = 14.689 (6) Å	µ = 1.03 mm⁻¹
c = 15.553 (4) Å	T = 291 K
β = 123.540 (11)°	Block, blue
V = 2220.5 (12) Å³	0.20 × 0.19 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4960 independent reflections
Radiation source: fine-focus sealed tube	3854 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scan	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.818, T_max = 0.838	k = −19→19
21143 measured reflections	l = −19→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0469P)² + 0.2754P] where P = (F_o² + 2F_c²)/3
4960 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Cu(C₂H₃O₂)₂(C₁₈H₁₆N₂O₂)]·H₂O	V = 2220.5 (12) Å³
M_r = 491.98	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.661 (3) Å	µ = 1.03 mm⁻¹
b = 14.689 (6) Å	T = 291 K
c = 15.553 (4) Å	0.20 × 0.19 × 0.18 mm
β = 123.540 (11)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4960 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3854 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.838	R_int = 0.043
21143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	Δρ_max = 0.28 e Å⁻³
4960 reflections	Δρ_min = −0.28 e Å⁻³
291 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 > σ(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
Cu1	0.19750 (2)	0.638427 (17)	0.351821 (17)	0.02824 (9)
O1	0.43387 (14)	0.58511 (11)	0.40262 (11)	0.0360 (3)
O2	0.23187 (14)	0.59585 (11)	0.21381 (11)	0.0379 (4)
O3	0.26556 (16)	0.75769 (10)	0.34343 (12)	0.0394 (4)
O4	0.13698 (19)	0.81284 (13)	0.39686 (14)	0.0531 (5)
O5	0.15262 (15)	0.51145 (10)	0.35769 (11)	0.0352 (3)
O6	0.00215 (19)	0.56093 (13)	0.39381 (14)	0.0533 (5)
N1	0.33015 (19)	0.64394 (11)	0.50978 (13)	0.0319 (4)
N2	0.01307 (18)	0.65453 (12)	0.20902 (13)	0.0315 (4)
C1	0.2732 (3)	0.66269 (16)	0.56418 (17)	0.0400 (5)
H1	0.1779	0.6651	0.5294	0.048*
C2	0.3524 (3)	0.67823 (18)	0.66939 (19)	0.0513 (6)
H2	0.3115	0.6921	0.7049	0.062*
C3	0.4931 (3)	0.6726 (2)	0.72009 (18)	0.0585 (7)
H3	0.5486	0.6836	0.7907	0.070*
C4	0.5530 (3)	0.65064 (18)	0.66613 (18)	0.0503 (6)
H4	0.6479	0.6443	0.7003	0.060*
C5	0.4679 (2)	0.63844 (15)	0.56047 (16)	0.0347 (5)
C6	0.5334 (2)	0.62142 (17)	0.50060 (17)	0.0400 (5)
H6A	0.5692	0.6780	0.4924	0.048*
H6B	0.6093	0.5790	0.5381	0.048*
C7	0.4697 (2)	0.58313 (15)	0.33102 (16)	0.0336 (5)
C8	0.6037 (2)	0.57611 (17)	0.35554 (19)	0.0432 (6)
H8	0.6772	0.5743	0.4242	0.052*
C9	0.6276 (3)	0.57171 (19)	0.2769 (2)	0.0532 (7)
H9	0.7170	0.5673	0.2929	0.064*
C10	0.5183 (3)	0.57400 (19)	0.1761 (2)	0.0525 (7)
H10	0.5343	0.5704	0.1238	0.063*
C11	0.3831 (3)	0.58167 (17)	0.15022 (19)	0.0440 (6)
H11	0.3098	0.5833	0.0814	0.053*
C12	0.3594 (2)	0.58687 (14)	0.22831 (16)	0.0325 (5)
C13	0.1171 (2)	0.61228 (17)	0.11292 (16)	0.0387 (5)
H13A	0.0978	0.5588	0.0704	0.046*
H13B	0.1364	0.6627	0.0825	0.046*
C14	−0.0064 (2)	0.63471 (15)	0.11764 (16)	0.0328 (4)
C15	−0.1366 (2)	0.63615 (18)	0.02673 (17)	0.0467 (6)
H15	−0.1481	0.6222	−0.0359	0.056*
C16	−0.2490 (3)	0.65856 (19)	0.0306 (2)	0.0526 (7)
H16	−0.3370	0.6584	−0.0293	0.063*
C17	−0.2301 (2)	0.68105 (18)	0.12371 (19)	0.0454 (6)
H17	−0.3041	0.6975	0.1275	0.054*
C18	−0.0983 (2)	0.67845 (16)	0.21095 (17)	0.0369 (5)
H18	−0.0849	0.6937	0.2739	0.044*
C19	0.2749 (4)	0.91611 (19)	0.3717 (2)	0.0691 (9)
H19A	0.3666	0.9223	0.4319	0.104*
H19B	0.2168	0.9618	0.3728	0.104*
H19C	0.2763	0.9235	0.3110	0.104*
C20	0.2198 (3)	0.82288 (17)	0.37095 (16)	0.0406 (5)
C21	0.0351 (3)	0.40102 (19)	0.3948 (2)	0.0531 (6)
H21A	−0.0609	0.3877	0.3477	0.080*
H21B	0.0603	0.3919	0.4643	0.080*
H21C	0.0887	0.3614	0.3811	0.080*
C22	0.0622 (2)	0.49872 (16)	0.38126 (16)	0.0368 (5)
O7	0.1077 (2)	0.40557 (15)	0.17760 (17)	0.0729 (6)
H71	0.0314	0.3772	0.1505	0.109*
H72	0.1223	0.4355	0.2295	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02986 (14)	0.03193 (14)	0.02291 (13)	−0.00047 (11)	0.01457 (11)	0.00016 (10)
O1	0.0302 (7)	0.0476 (10)	0.0287 (8)	−0.0046 (7)	0.0153 (7)	−0.0046 (7)
O2	0.0285 (7)	0.0602 (11)	0.0254 (7)	0.0034 (7)	0.0152 (7)	−0.0004 (7)
O3	0.0487 (9)	0.0370 (9)	0.0358 (8)	−0.0042 (7)	0.0254 (8)	−0.0001 (7)
O4	0.0606 (11)	0.0524 (11)	0.0561 (11)	0.0162 (9)	0.0384 (10)	0.0136 (9)
O5	0.0353 (8)	0.0358 (8)	0.0345 (8)	−0.0041 (6)	0.0193 (7)	−0.0006 (6)
O6	0.0604 (11)	0.0581 (12)	0.0542 (11)	0.0101 (9)	0.0397 (10)	0.0089 (9)
N1	0.0400 (10)	0.0301 (9)	0.0247 (8)	−0.0018 (8)	0.0173 (8)	0.0000 (7)
N2	0.0314 (9)	0.0360 (10)	0.0272 (9)	0.0014 (7)	0.0163 (8)	0.0017 (7)
C1	0.0528 (14)	0.0394 (13)	0.0335 (12)	−0.0003 (10)	0.0274 (12)	0.0016 (9)
C2	0.0784 (19)	0.0500 (15)	0.0348 (13)	−0.0035 (14)	0.0372 (14)	−0.0017 (11)
C3	0.077 (2)	0.0650 (18)	0.0212 (11)	−0.0089 (15)	0.0193 (13)	−0.0039 (11)
C4	0.0500 (15)	0.0558 (17)	0.0300 (12)	−0.0082 (12)	0.0125 (12)	0.0019 (11)
C5	0.0396 (12)	0.0301 (11)	0.0275 (10)	−0.0034 (9)	0.0141 (10)	0.0020 (9)
C6	0.0328 (11)	0.0457 (14)	0.0327 (11)	−0.0070 (10)	0.0126 (10)	−0.0034 (10)
C7	0.0347 (11)	0.0347 (12)	0.0363 (12)	0.0012 (9)	0.0226 (10)	0.0000 (9)
C8	0.0326 (12)	0.0491 (15)	0.0467 (14)	0.0044 (10)	0.0213 (12)	0.0004 (11)
C9	0.0452 (14)	0.0641 (18)	0.0663 (18)	0.0055 (12)	0.0408 (15)	−0.0027 (14)
C10	0.0540 (15)	0.0651 (18)	0.0588 (17)	0.0042 (13)	0.0439 (15)	−0.0010 (13)
C11	0.0454 (13)	0.0550 (16)	0.0400 (13)	0.0024 (11)	0.0288 (12)	−0.0016 (11)
C12	0.0327 (11)	0.0340 (12)	0.0354 (11)	0.0003 (9)	0.0216 (10)	−0.0022 (9)
C13	0.0365 (12)	0.0523 (14)	0.0260 (11)	0.0034 (10)	0.0164 (10)	0.0011 (9)
C14	0.0341 (11)	0.0356 (12)	0.0274 (10)	0.0001 (9)	0.0163 (10)	0.0012 (9)
C15	0.0424 (13)	0.0627 (17)	0.0261 (11)	0.0087 (12)	0.0133 (11)	0.0013 (11)
C16	0.0332 (12)	0.074 (2)	0.0350 (13)	0.0103 (12)	0.0089 (11)	0.0045 (12)
C17	0.0366 (12)	0.0519 (15)	0.0456 (14)	0.0120 (11)	0.0215 (12)	0.0096 (11)
C18	0.0376 (12)	0.0398 (13)	0.0344 (11)	0.0070 (10)	0.0206 (11)	0.0040 (10)
C19	0.116 (3)	0.0406 (16)	0.0568 (17)	−0.0208 (16)	0.0513 (19)	−0.0090 (13)
C20	0.0542 (15)	0.0365 (13)	0.0269 (11)	0.0013 (11)	0.0199 (11)	0.0057 (9)
C21	0.0548 (15)	0.0511 (16)	0.0530 (16)	−0.0142 (13)	0.0295 (14)	0.0008 (12)
C22	0.0347 (11)	0.0441 (13)	0.0277 (11)	−0.0024 (10)	0.0146 (10)	0.0012 (9)
O7	0.0755 (14)	0.0811 (16)	0.0852 (15)	−0.0315 (12)	0.0590 (14)	−0.0353 (12)

Geometric parameters (Å, º) top

Cu1—O5	1.9529 (16)	C7—C8	1.393 (3)
Cu1—O3	1.9571 (16)	C8—C9	1.398 (3)
Cu1—N1	2.0580 (18)	C8—H8	0.9300
Cu1—N2	2.0823 (18)	C9—C10	1.370 (4)
Cu1—O2	2.4719 (15)	C9—H9	0.9300
Cu1—O1	2.5353 (16)	C10—C11	1.401 (3)
O1—C7	1.389 (2)	C10—H10	0.9300
O1—C6	1.414 (3)	C11—C12	1.389 (3)
O2—C12	1.381 (2)	C11—H11	0.9300
O2—C13	1.411 (3)	C13—C14	1.519 (3)
O3—C20	1.280 (3)	C13—H13A	0.9700
O4—C20	1.244 (3)	C13—H13B	0.9700
O5—C22	1.307 (3)	C14—C15	1.390 (3)
O6—C22	1.231 (3)	C15—C16	1.385 (3)
N1—C5	1.345 (3)	C15—H15	0.9300
N1—C1	1.362 (3)	C16—C17	1.378 (3)
N2—C14	1.341 (3)	C16—H16	0.9300
N2—C18	1.362 (3)	C17—C18	1.378 (3)
C1—C2	1.383 (3)	C17—H17	0.9300
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.376 (4)	C19—C20	1.510 (3)
C2—H2	0.9300	C19—H19A	0.9600
C3—C4	1.394 (4)	C19—H19B	0.9600
C3—H3	0.9300	C19—H19C	0.9600
C4—C5	1.384 (3)	C21—C22	1.509 (3)
C4—H4	0.9300	C21—H21A	0.9600
C5—C6	1.516 (3)	C21—H21B	0.9600
C6—H6A	0.9700	C21—H21C	0.9600
C6—H6B	0.9700	O7—H71	0.8527
C7—C12	1.392 (3)	O7—H72	0.8496

O5—Cu1—O3	170.76 (6)	C7—C8—H8	120.0
O5—Cu1—N1	91.48 (6)	C9—C8—H8	120.0
O3—Cu1—N1	88.82 (7)	C10—C9—C8	119.4 (2)
O5—Cu1—N2	90.74 (7)	C10—C9—H9	120.3
O3—Cu1—N2	92.58 (7)	C8—C9—H9	120.3
N1—Cu1—N2	157.06 (7)	C9—C10—C11	121.2 (2)
O5—Cu1—O2	88.58 (6)	C9—C10—H10	119.4
O3—Cu1—O2	84.40 (6)	C11—C10—H10	119.4
N1—Cu1—O2	132.15 (6)	C12—C11—C10	119.3 (2)
N2—Cu1—O2	70.73 (6)	C12—C11—H11	120.3
O5—Cu1—O1	87.92 (6)	C10—C11—H11	120.3
O3—Cu1—O1	83.47 (6)	O2—C12—C11	125.4 (2)
N1—Cu1—O1	70.70 (6)	O2—C12—C7	114.82 (17)
N2—Cu1—O1	132.21 (6)	C11—C12—C7	119.81 (19)
O2—Cu1—O1	61.48 (5)	O2—C13—C14	109.00 (16)
C7—O1—C6	116.14 (16)	O2—C13—H13A	109.9
C7—O1—Cu1	120.87 (12)	C14—C13—H13A	109.9
C6—O1—Cu1	108.85 (12)	O2—C13—H13B	109.9
C12—O2—C13	118.16 (16)	C14—C13—H13B	109.9
C12—O2—Cu1	123.96 (12)	H13A—C13—H13B	108.3
C13—O2—Cu1	114.41 (12)	N2—C14—C15	121.7 (2)
C20—O3—Cu1	112.84 (14)	N2—C14—C13	119.23 (18)
C22—O5—Cu1	115.36 (14)	C15—C14—C13	119.09 (19)
C5—N1—C1	118.86 (19)	C16—C15—C14	119.2 (2)
C5—N1—Cu1	124.32 (14)	C16—C15—H15	120.4
C1—N1—Cu1	116.53 (15)	C14—C15—H15	120.4
C14—N2—C18	118.30 (18)	C17—C16—C15	119.8 (2)
C14—N2—Cu1	125.17 (14)	C17—C16—H16	120.1
C18—N2—Cu1	116.19 (14)	C15—C16—H16	120.1
N1—C1—C2	122.2 (2)	C18—C17—C16	118.2 (2)
N1—C1—H1	118.9	C18—C17—H17	120.9
C2—C1—H1	118.9	C16—C17—H17	120.9
C3—C2—C1	118.3 (2)	N2—C18—C17	122.9 (2)
C3—C2—H2	120.9	N2—C18—H18	118.5
C1—C2—H2	120.9	C17—C18—H18	118.5
C2—C3—C4	120.3 (2)	C20—C19—H19A	109.5
C2—C3—H3	119.9	C20—C19—H19B	109.5
C4—C3—H3	119.9	H19A—C19—H19B	109.5
C5—C4—C3	118.4 (2)	C20—C19—H19C	109.5
C5—C4—H4	120.8	H19A—C19—H19C	109.5
C3—C4—H4	120.8	H19B—C19—H19C	109.5
N1—C5—C4	121.9 (2)	O4—C20—O3	124.2 (2)
N1—C5—C6	119.58 (18)	O4—C20—C19	120.5 (2)
C4—C5—C6	118.5 (2)	O3—C20—C19	115.3 (2)
O1—C6—C5	109.39 (18)	C22—C21—H21A	109.5
O1—C6—H6A	109.8	C22—C21—H21B	109.5
C5—C6—H6A	109.8	H21A—C21—H21B	109.5
O1—C6—H6B	109.8	C22—C21—H21C	109.5
C5—C6—H6B	109.8	H21A—C21—H21C	109.5
H6A—C6—H6B	108.2	H21B—C21—H21C	109.5
O1—C7—C12	115.01 (17)	O6—C22—O5	123.8 (2)
O1—C7—C8	124.8 (2)	O6—C22—C21	120.1 (2)
C12—C7—C8	120.17 (19)	O5—C22—C21	116.0 (2)
C7—C8—C9	120.0 (2)	H71—O7—H72	109.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H71···O4ⁱ	0.85	1.92	2.772 (3)	174
O7—H72···O5	0.85	2.14	2.986 (2)	178

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H₃O₂)₂(C₁₈H₁₆N₂O₂)]·H₂O
M_r	491.98
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	11.661 (3), 14.689 (6), 15.553 (4)
β (°)	123.540 (11)
V (Å³)	2220.5 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.20 × 0.19 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.818, 0.838
No. of measured, independent and observed [I > 2σ(I)] reflections	21143, 4960, 3854
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.05
No. of reflections	4960
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O5	1.9529 (16)	Cu1—N2	2.0823 (18)
Cu1—O3	1.9571 (16)	Cu1—O2	2.4719 (15)
Cu1—N1	2.0580 (18)	Cu1—O1	2.5353 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H71···O4ⁱ	0.85	1.92	2.772 (3)	174.2
O7—H72···O5	0.85	2.14	2.986 (2)	178.3

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

The authors thank the Special Funds for the Research of Scientific and Technological Innovative Talents of Harbin Municipal Science and Technology Bureau (2006RFQXG093) and Heilongjiang University for supporting this study.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Liu, Y., Yan, P.-F., Yu, Y.-H., Hou, G.-F. & Gao, J.-S. (2010a). Cryst. Growth Des. 10, 1559–1568. Web of Science CSD CrossRef CAS Google Scholar
Liu, Y., Yan, P.-F., Yu, Y.-H., Hou, G.-F. & Gao, J.-S. (2010b). Inorg. Chem. Commun. 13, 630–632. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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