Bis(μ-2-phenyl­acetato-κ2O:O)bis­[(2,2′-bipyridyl-κ2N,N′)(2-phenyl­acetato-κO)copper(II)] dihydrate

Xu, W.; Jin, L.; Liu, B.-B.

doi:10.1107/S1600536811035483

metal-organic compounds

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Volume 67| Part 10| October 2011| Page m1334

https://doi.org/10.1107/S1600536811035483

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Bis(μ-2-phenylacetato-κ²O:O)bis[(2,2′-bipyridyl-κ²N,N′)(2-phenylacetato-κO)copper(II)] dihydrate

Wei Xu,^a ^* Ling Jin ^a and Bin-Bin Liu ^a

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: xuwei@nbu.edu.cn

(Received 16 June 2011; accepted 31 August 2011; online 14 September 2011)

The molecule of the binuclear title complex, [Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂]·2H₂O, is located on an inversion centre. The Cu atoms are bridged by two O atoms of the monodentate phenylacetate groups [Cu—O = 1.9808 (14) and 2.3668 (14) Å]. The longer of the two bridging Cu—O bonds takes the apical position of the distorted square-pyramidal environment of the Cu atom, which is completed by two N atoms of the chelate 2,2′-bipyridine ligand [Cu—N = 2.0107 (17) and 2.0234 (16) Å]. The molecules are assembled into stacks along [100] through π–π interactions with interplanar distances of 3.630 (4) and 3.407 (3) Å; the resulting stacks are further connected into a three-dimensional supramolecular architecture by O—H⋯O and C—H⋯O hydrogen-bonding interactions.

Related literature

For applications of inorganic–organic hybrid materials, see: Pan et al. (2003 ); Shibasaki & Yoshikawa (2002 ). For related structures, see: Addison & Rao (1984 ); Antolini et al. (1985 ); Zhang et al. (2006 ).

Experimental

Crystal data

[Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂]·2H₂O
M_r = 1016.02
Monoclinic, P 2₁ /n
a = 10.213 (2) Å
b = 16.058 (3) Å
c = 14.633 (3) Å
β = 100.75 (3)°
V = 2357.7 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 295 K
0.17 × 0.14 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.678, T_max = 0.784
22348 measured reflections
5356 independent reflections
4268 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.090
S = 1.10
5356 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4	0.85	2.05	2.781 (3)	143
O5—H52⋯O2ⁱ	0.86	2.08	2.931 (3)	174
C20—H20A⋯O4ⁱⁱ	0.93	2.38	3.245 (3)	156
C24—H24A⋯O2ⁱⁱⁱ	0.93	2.48	3.172 (3)	131
C25—H25A⋯O5^iv	0.93	2.50	3.201 (3)	132
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y, -z; (iii) x-1, y, z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035483/ya2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035483/ya2144Isup2.hkl

checkCIF report

Comment top

The use of metal centers for organizing of molecular building blocks into inorganic–organic hybrid materials have been studied for potential applications in catalysis, gas storage, and in molecular–based magnetic materials (Pan et al., 2003; Shibasaki & Yoshikawa, 2002). As part of our investigations of self-assemblies of Cu²⁺ ions and bipy with phenylacetic acid, we prepared the title complex, [Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂].2H₂O.

The molecule of the complex occupies a special position in the inversion centre (Fig. 1). The square pyramidal coordination environment of the Cu atom is formed by the N atoms of 2,2'-bipyridine ligands (Cu—N1 2.0108 (17) Å and Cu—N2 2.0234 (16) Å), the O atom of terminal phenylacetato ligand (Cu—O3 1.9557 (16) Å), and two O atoms of bridging phenylacetato groups, the O1ⁱ atom [symmetry code (i): 1 - x, -y, -z] takes one of the equatorial positions, whereas the O1 atom occupies the apical site. As one would expect (Antolini et al., 1985; Zhang et al., 2006), the apical bond Cu—O1 2.3669 (14) Å is substantially longer than the equatorial Cu—O1ⁱ distance of 1.9807 (14) Å. The Cu atom is displaced by 0.078 (1) Å towards the apical vertex from the mean plane of the equatorial ligands [τ = 0.04 according to Addison & Rao (1984)].

The molecules are assembled into stacks along [100] through π···π stacking interactions with the mean interplanar distance of 3.407 (3) Å between adjacent bipy ligands and 3.630 (4) Å between bipy ligands and phenylacetato groups, and the stacks are further stabilized by the weak C—H···O hydrogen bonding interactions from the phenyl CH groups to the uncoordinating carboxylate O2 and O4 atoms (Table 1), as well O—H···O bonds involving water molecule (Fig. 2). As a result, three-dimensional network is formed.

Related literature top

For applications of inorganic–organic hybrid materials , see: Pan et al. (2003); Shibasaki & Yoshikawa (2002). For related structures, see: Addison & Rao (1984); Antolini et al. (1985); Zhang et al. (2006).

Experimental top

Phenylacetic acid(0.2726 g, 2.000 mmol) was completely dissolved in a mixture of 10 ml of ethanol, 10 ml of water, and bipy (0.1561 g, 1.000 mmol). 0.2602 g (1.084 mmol) of Cu(NO₃)₂.3H₂O were then added, and after dropwise addition of 2.0 ml (1M) NaOH to the resulting solution under continuous stirring for 1 h, the blue suspension was produced. The suspension was filtered and the filtrate (pH = 6.51) was allowed to stand at room temperature for several weeks; the precipitation of blue block crystals was observed.

Structure description top

For applications of inorganic–organic hybrid materials , see: Pan et al. (2003); Shibasaki & Yoshikawa (2002). For related structures, see: Addison & Rao (1984); Antolini et al. (1985); Zhang et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound. The displacement ellipsoids are drawn at 45% probability level; hydrogen atoms bonded to carbon were omitted.
	Fig. 2. Crystal packing of the title complex viewed down the c axis. Hydrogen bonds are shown as dashed lines.

Bis(µ-2-phenylacetato-κ²O:O)bis[(2,2'- bipyridyl-κ²N,N')(2-phenylacetato-κO)copper(II)] dihydrate top

Crystal data top

[Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂]·2H₂O	F(000) = 1052
M_r = 1016.02	D_x = 1.431 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 22348 reflections
a = 10.213 (2) Å	θ = 3.1–27.4°
b = 16.058 (3) Å	µ = 0.97 mm⁻¹
c = 14.633 (3) Å	T = 295 K
β = 100.75 (3)°	Block, blue
V = 2357.7 (8) Å³	0.17 × 0.14 × 0.11 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	5356 independent reflections
Radiation source: fine-focus sealed tube	4268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 0 pixels mm^-1	θ_max = 27.4°, θ_min = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −20→20
T_min = 0.678, T_max = 0.784	l = −18→18
22348 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0357P)² + 1.1037P] where P = (F_o² + 2F_c²)/3
5356 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂]·2H₂O	V = 2357.7 (8) Å³
M_r = 1016.02	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.213 (2) Å	µ = 0.97 mm⁻¹
b = 16.058 (3) Å	T = 295 K
c = 14.633 (3) Å	0.17 × 0.14 × 0.11 mm
β = 100.75 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5356 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4268 reflections with I > 2σ(I)
T_min = 0.678, T_max = 0.784	R_int = 0.033
22348 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.10	Δρ_max = 0.29 e Å⁻³
5356 reflections	Δρ_min = −0.56 e Å⁻³
307 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cu	0.34936 (2)	0.003603 (15)	0.032956 (16)	0.03079 (8)
O1	0.51708 (12)	0.08258 (8)	−0.01885 (10)	0.0349 (3)
O2	0.65975 (14)	0.18355 (10)	−0.03382 (12)	0.0509 (4)
C1	0.54722 (19)	0.15958 (13)	−0.02762 (13)	0.0335 (4)
C2	0.4344 (2)	0.22176 (13)	−0.03118 (15)	0.0390 (5)
H2A	0.3904	0.2116	0.0211	0.047*
H2B	0.4716	0.2775	−0.0244	0.047*
C3	0.33151 (19)	0.21773 (12)	−0.12042 (15)	0.0371 (4)
C4	0.3645 (3)	0.18987 (17)	−0.20253 (17)	0.0583 (7)
H4A	0.4507	0.1714	−0.2029	0.070*
C5	0.2707 (3)	0.1891 (2)	−0.2844 (2)	0.0775 (9)
H5A	0.2943	0.1704	−0.3393	0.093*
C6	0.1426 (3)	0.2159 (2)	−0.2846 (2)	0.0747 (9)
H6A	0.0796	0.2149	−0.3394	0.090*
C7	0.1079 (2)	0.24395 (17)	−0.2039 (2)	0.0633 (8)
H7A	0.0213	0.2620	−0.2039	0.076*
C8	0.2023 (2)	0.24547 (14)	−0.12211 (17)	0.0467 (5)
H8A	0.1786	0.2654	−0.0678	0.056*
O3	0.43667 (14)	0.02350 (11)	0.16182 (10)	0.0444 (4)
O4	0.28773 (16)	−0.06110 (11)	0.20372 (11)	0.0555 (4)
C9	0.3872 (2)	−0.01680 (15)	0.22212 (14)	0.0411 (5)
C10	0.4592 (2)	−0.00598 (19)	0.32311 (16)	0.0596 (7)
H10A	0.5128	−0.0550	0.3420	0.071*
H10B	0.5188	0.0414	0.3269	0.071*
C11	0.3641 (2)	0.00710 (15)	0.38924 (15)	0.0456 (5)
C12	0.3061 (3)	−0.05839 (18)	0.42846 (19)	0.0650 (7)
H12A	0.3274	−0.1128	0.4152	0.078*
C13	0.2172 (3)	−0.0439 (2)	0.4869 (2)	0.0742 (8)
H13A	0.1795	−0.0887	0.5129	0.089*
C14	0.1839 (3)	0.0353 (2)	0.50716 (18)	0.0636 (7)
H14A	0.1238	0.0447	0.5467	0.076*
C15	0.2394 (3)	0.10011 (19)	0.46888 (19)	0.0631 (7)
H15A	0.2170	0.1543	0.4821	0.076*
C16	0.3284 (3)	0.08655 (17)	0.41081 (18)	0.0563 (6)
H16A	0.3655	0.1319	0.3854	0.068*
N1	0.23495 (15)	−0.01459 (10)	−0.09298 (11)	0.0314 (3)
N2	0.19920 (15)	0.08350 (10)	0.04221 (11)	0.0325 (3)
C17	0.2643 (2)	−0.06336 (14)	−0.16069 (14)	0.0391 (5)
H17A	0.3461	−0.0906	−0.1511	0.047*
C18	0.1775 (2)	−0.07459 (15)	−0.24405 (15)	0.0466 (5)
H18A	0.2003	−0.1090	−0.2898	0.056*
C19	0.0565 (2)	−0.03411 (16)	−0.25860 (16)	0.0495 (6)
H19A	−0.0037	−0.0413	−0.3141	0.059*
C20	0.0255 (2)	0.01729 (14)	−0.18992 (15)	0.0427 (5)
H20A	−0.0553	0.0456	−0.1988	0.051*
C21	0.11684 (18)	0.02584 (12)	−0.10760 (13)	0.0312 (4)
C22	0.09470 (17)	0.07952 (12)	−0.02961 (13)	0.0306 (4)
C23	−0.02197 (19)	0.12337 (13)	−0.02906 (15)	0.0383 (5)
H23A	−0.0940	0.1183	−0.0781	0.046*
C24	−0.0295 (2)	0.17477 (14)	0.04555 (16)	0.0440 (5)
H24A	−0.1070	0.2047	0.0473	0.053*
C25	0.0786 (2)	0.18136 (14)	0.11732 (16)	0.0452 (5)
H25A	0.0763	0.2170	0.1671	0.054*
C26	0.1906 (2)	0.13390 (14)	0.11387 (15)	0.0405 (5)
H26A	0.2626	0.1371	0.1631	0.049*
O5	0.2460 (2)	−0.23227 (13)	0.20341 (15)	0.0773 (6)
H51	0.2485	−0.1839	0.2272	0.116*
H52	0.2711	−0.2215	0.1520	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.02265 (12)	0.03791 (15)	0.03088 (13)	0.00331 (9)	0.00258 (8)	−0.00214 (10)
O1	0.0285 (6)	0.0323 (7)	0.0433 (8)	0.0024 (5)	0.0051 (6)	0.0023 (6)
O2	0.0342 (8)	0.0455 (9)	0.0739 (11)	−0.0039 (7)	0.0121 (7)	0.0069 (8)
C1	0.0320 (10)	0.0356 (11)	0.0312 (10)	0.0014 (8)	0.0019 (8)	−0.0005 (8)
C2	0.0400 (11)	0.0334 (11)	0.0426 (11)	0.0032 (9)	0.0055 (9)	−0.0029 (9)
C3	0.0351 (10)	0.0321 (10)	0.0428 (11)	0.0030 (8)	0.0039 (8)	0.0058 (9)
C4	0.0551 (14)	0.0698 (18)	0.0468 (14)	0.0191 (13)	0.0007 (11)	−0.0008 (13)
C5	0.090 (2)	0.090 (2)	0.0448 (15)	0.0176 (18)	−0.0081 (14)	−0.0041 (15)
C6	0.0710 (19)	0.075 (2)	0.0636 (19)	0.0014 (16)	−0.0254 (15)	0.0121 (15)
C7	0.0376 (12)	0.0606 (17)	0.086 (2)	0.0029 (11)	−0.0042 (13)	0.0222 (15)
C8	0.0377 (11)	0.0428 (12)	0.0599 (14)	0.0023 (9)	0.0099 (10)	0.0093 (11)
O3	0.0309 (7)	0.0674 (10)	0.0337 (8)	0.0018 (7)	0.0031 (6)	−0.0036 (7)
O4	0.0500 (9)	0.0661 (11)	0.0491 (10)	−0.0099 (8)	0.0062 (7)	−0.0053 (8)
C9	0.0315 (10)	0.0574 (14)	0.0335 (11)	0.0116 (10)	0.0037 (8)	−0.0074 (10)
C10	0.0410 (12)	0.100 (2)	0.0355 (12)	0.0106 (13)	0.0012 (9)	−0.0053 (13)
C11	0.0457 (12)	0.0607 (15)	0.0286 (10)	0.0041 (11)	0.0024 (9)	0.0002 (10)
C12	0.090 (2)	0.0494 (15)	0.0579 (16)	0.0079 (14)	0.0187 (15)	0.0018 (13)
C13	0.096 (2)	0.071 (2)	0.0629 (18)	−0.0154 (18)	0.0345 (16)	0.0074 (16)
C14	0.0631 (16)	0.085 (2)	0.0467 (15)	−0.0023 (15)	0.0211 (12)	−0.0068 (15)
C15	0.0716 (18)	0.0637 (17)	0.0549 (16)	0.0097 (14)	0.0144 (13)	−0.0113 (13)
C16	0.0660 (16)	0.0532 (15)	0.0509 (14)	−0.0050 (12)	0.0140 (12)	0.0018 (12)
N1	0.0259 (7)	0.0354 (9)	0.0325 (8)	0.0004 (6)	0.0044 (6)	−0.0008 (7)
N2	0.0259 (7)	0.0372 (9)	0.0340 (8)	0.0012 (7)	0.0046 (6)	−0.0020 (7)
C17	0.0321 (10)	0.0462 (12)	0.0395 (11)	0.0043 (9)	0.0080 (8)	−0.0070 (9)
C18	0.0477 (12)	0.0546 (14)	0.0372 (11)	0.0004 (11)	0.0071 (9)	−0.0115 (10)
C19	0.0462 (13)	0.0617 (15)	0.0358 (12)	0.0001 (11)	−0.0044 (9)	−0.0055 (11)
C20	0.0333 (10)	0.0501 (13)	0.0413 (12)	0.0052 (9)	−0.0018 (9)	0.0010 (10)
C21	0.0260 (9)	0.0332 (10)	0.0341 (10)	−0.0011 (7)	0.0048 (7)	0.0023 (8)
C22	0.0256 (8)	0.0330 (10)	0.0330 (10)	−0.0009 (8)	0.0052 (7)	0.0034 (8)
C23	0.0282 (9)	0.0416 (11)	0.0440 (11)	0.0037 (8)	0.0040 (8)	0.0025 (9)
C24	0.0323 (10)	0.0449 (12)	0.0565 (14)	0.0080 (9)	0.0125 (9)	−0.0031 (10)
C25	0.0416 (11)	0.0467 (13)	0.0492 (13)	0.0034 (10)	0.0135 (10)	−0.0125 (10)
C26	0.0339 (10)	0.0462 (12)	0.0405 (11)	0.0011 (9)	0.0046 (8)	−0.0085 (10)
O5	0.0807 (14)	0.0718 (13)	0.0769 (14)	−0.0005 (11)	0.0082 (11)	0.0222 (11)

Geometric parameters (Å, º) top

Cu—O3	1.9558 (15)	C12—H12A	0.9300
Cu—O1ⁱ	1.9808 (14)	C13—C14	1.363 (4)
Cu—N1	2.0107 (17)	C13—H13A	0.9300
Cu—N2	2.0234 (16)	C14—C15	1.356 (4)
Cu—O1	2.3668 (14)	C14—H14A	0.9300
O1—C1	1.286 (2)	C15—C16	1.372 (4)
O1—Cuⁱ	1.9808 (14)	C15—H15A	0.9300
O2—C1	1.231 (2)	C16—H16A	0.9300
C1—C2	1.518 (3)	N1—C17	1.340 (3)
C2—C3	1.517 (3)	N1—C21	1.351 (2)
C2—H2A	0.9700	N2—C26	1.340 (3)
C2—H2B	0.9700	N2—C22	1.352 (2)
C3—C4	1.381 (3)	C17—C18	1.380 (3)
C3—C8	1.389 (3)	C17—H17A	0.9300
C4—C5	1.388 (4)	C18—C19	1.377 (3)
C4—H4A	0.9300	C18—H18A	0.9300
C5—C6	1.377 (4)	C19—C20	1.382 (3)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.371 (4)	C20—C21	1.386 (3)
C6—H6A	0.9300	C20—H20A	0.9300
C7—C8	1.390 (3)	C21—C22	1.481 (3)
C7—H7A	0.9300	C22—C23	1.385 (3)
C8—H8A	0.9300	C23—C24	1.382 (3)
O3—C9	1.272 (3)	C23—H23A	0.9300
O4—C9	1.228 (3)	C24—C25	1.379 (3)
C9—C10	1.533 (3)	C24—H24A	0.9300
C10—C11	1.508 (3)	C25—C26	1.383 (3)
C10—H10A	0.9700	C25—H25A	0.9300
C10—H10B	0.9700	C26—H26A	0.9300
C11—C16	1.380 (3)	O5—H51	0.8494
C11—C12	1.383 (4)	O5—H52	0.8560
C12—C13	1.379 (4)

O3—Cu—O1ⁱ	90.90 (6)	C13—C12—C11	120.8 (3)
O3—Cu—N1	171.79 (6)	C13—C12—H12A	119.6
O1ⁱ—Cu—N1	95.55 (6)	C11—C12—H12A	119.6
O3—Cu—N2	92.68 (7)	C14—C13—C12	120.8 (3)
O1ⁱ—Cu—N2	174.44 (6)	C14—C13—H13A	119.6
N1—Cu—N2	80.52 (7)	C12—C13—H13A	119.6
O3—Cu—O1	89.67 (6)	C15—C14—C13	119.1 (3)
O1ⁱ—Cu—O1	77.72 (6)	C15—C14—H14A	120.5
N1—Cu—O1	96.65 (6)	C13—C14—H14A	120.5
N2—Cu—O1	106.54 (6)	C14—C15—C16	120.7 (3)
C1—O1—Cuⁱ	118.61 (12)	C14—C15—H15A	119.7
C1—O1—Cu	138.41 (12)	C16—C15—H15A	119.7
Cuⁱ—O1—Cu	102.28 (6)	C15—C16—C11	121.5 (3)
O2—C1—O1	123.49 (18)	C15—C16—H16A	119.3
O2—C1—C2	120.32 (19)	C11—C16—H16A	119.3
O1—C1—C2	116.18 (17)	C17—N1—C21	118.68 (17)
C3—C2—C1	113.63 (17)	C17—N1—Cu	126.20 (13)
C3—C2—H2A	108.8	C21—N1—Cu	115.11 (13)
C1—C2—H2A	108.8	C26—N2—C22	118.62 (16)
C3—C2—H2B	108.8	C26—N2—Cu	126.61 (13)
C1—C2—H2B	108.8	C22—N2—Cu	114.59 (13)
H2A—C2—H2B	107.7	N1—C17—C18	122.32 (19)
C4—C3—C8	118.3 (2)	N1—C17—H17A	118.8
C4—C3—C2	121.36 (19)	C18—C17—H17A	118.8
C8—C3—C2	120.3 (2)	C19—C18—C17	119.0 (2)
C3—C4—C5	120.9 (2)	C19—C18—H18A	120.5
C3—C4—H4A	119.6	C17—C18—H18A	120.5
C5—C4—H4A	119.6	C18—C19—C20	119.4 (2)
C6—C5—C4	120.1 (3)	C18—C19—H19A	120.3
C6—C5—H5A	120.0	C20—C19—H19A	120.3
C4—C5—H5A	120.0	C19—C20—C21	118.9 (2)
C7—C6—C5	120.0 (2)	C19—C20—H20A	120.6
C7—C6—H6A	120.0	C21—C20—H20A	120.6
C5—C6—H6A	120.0	N1—C21—C20	121.75 (19)
C6—C7—C8	119.9 (2)	N1—C21—C22	114.69 (16)
C6—C7—H7A	120.1	C20—C21—C22	123.56 (18)
C8—C7—H7A	120.1	N2—C22—C23	121.76 (18)
C3—C8—C7	120.9 (2)	N2—C22—C21	114.49 (16)
C3—C8—H8A	119.5	C23—C22—C21	123.75 (17)
C7—C8—H8A	119.5	C24—C23—C22	118.88 (19)
C9—O3—Cu	114.65 (14)	C24—C23—H23A	120.6
O4—C9—O3	124.2 (2)	C22—C23—H23A	120.6
O4—C9—C10	120.3 (2)	C25—C24—C23	119.50 (19)
O3—C9—C10	115.5 (2)	C25—C24—H24A	120.3
C11—C10—C9	112.61 (19)	C23—C24—H24A	120.3
C11—C10—H10A	109.1	C24—C25—C26	118.7 (2)
C9—C10—H10A	109.1	C24—C25—H25A	120.6
C11—C10—H10B	109.1	C26—C25—H25A	120.6
C9—C10—H10B	109.1	N2—C26—C25	122.46 (19)
H10A—C10—H10B	107.8	N2—C26—H26A	118.8
C16—C11—C12	117.1 (2)	C25—C26—H26A	118.8
C16—C11—C10	120.3 (2)	H51—O5—H52	100.6
C12—C11—C10	122.5 (2)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.85	2.05	2.781 (3)	143
O5—H52···O2ⁱ	0.86	2.08	2.931 (3)	174
C20—H20A···O4ⁱⁱ	0.93	2.38	3.245 (3)	156
C24—H24A···O2ⁱⁱⁱ	0.93	2.48	3.172 (3)	131
C25—H25A···O5^iv	0.93	2.50	3.201 (3)	132

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₈H₇O₂)₄(C₁₀H₈N₂)₂]·2H₂O
M_r	1016.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.213 (2), 16.058 (3), 14.633 (3)
β (°)	100.75 (3)
V (Å³)	2357.7 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.17 × 0.14 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.678, 0.784
No. of measured, independent and observed [I > 2σ(I)] reflections	22348, 5356, 4268
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.090, 1.10
No. of reflections	5356
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.56

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4	0.85	2.05	2.781 (3)	143
O5—H52···O2ⁱ	0.86	2.08	2.931 (3)	174
C20—H20A···O4ⁱⁱ	0.93	2.38	3.245 (3)	156
C24—H24A···O2ⁱⁱⁱ	0.93	2.48	3.172 (3)	131
C25—H25A···O5^iv	0.93	2.50	3.201 (3)	132

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

This project was supported by the K. C. Wong Magna Fund in Ningbo University.

References

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