Bis(μ-biphenyl-2,2′-dicarboxyl­ato)bis­[aqua­(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)copper(II)]

Dong, X.-Y.; Xu, X.-J.; Yang, L.

doi:10.1107/S1600536809040628

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1360

https://doi.org/10.1107/S1600536809040628

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Bis(μ-biphenyl-2,2′-dicarboxylato)bis[aqua(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)copper(II)]

Xi-Yan Dong,^a ^* Xiao-Jie Xu ^a and Lei Yang ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, Henan, People's Republic of China
^*Correspondence e-mail: xiyandong@yeah.net

(Received 27 September 2009; accepted 6 October 2009; online 17 October 2009)

The molecule of the title binuclear copper(II) complex, [Cu₂(C₁₄H₈O₄)₂(C₁₂H₁₂N₂)₂(H₂O)₂], is bisected by a crystallographic twofold axis. Each Cu^II atom is coordinated in a distorted octahedral geometry by three O atoms from two biphenyl-2,2′-dicarboxylate anions, one aqua O atom and two N atoms of a 4,4′-dimethyl-2,2′-bipyridine ligand. Intramolecular O—H⋯O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms are also present.

Related literature

For related structures, see: Li et al. (2009 ); Jiang & Feng (2009 ); Xu et al. (2009 ); Zhang et al. (2009 ); Rizal & Ng (2009 ); Zhang (2009 ).

Experimental

Crystal data

[Cu₂(C₁₄H₈O₄)₂(C₁₂H₁₂N₂)₂(H₂O)₂]
M_r = 1109.71
Monoclinic, C 2/c
a = 17.104 (3) Å
b = 15.395 (2) Å
c = 18.289 (3) Å
β = 104.413 (3)°
V = 4664.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 296 K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.785, T_max = 0.814
13512 measured reflections
4594 independent reflections
3108 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 0.93
4594 reflections
310 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O4ⁱ	0.85	1.78	2.632 (4)	174
O1W—H1WA⋯O1ⁱ	0.85	1.95	2.782 (4)	164
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809040628/jh2107sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040628/jh2107Isup2.hkl

checkCIF report

Comment top

The title binuclear copper(II) complex, [Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)₂(H₂O)₂], is a centrosymmetric dimer. The asymmetric unit consitsts of one Cu^II atom, one 4,4'-dimethyl-2,2'-bipyridine (dbpy) ligand, one [1,1'-biphenyl]-2,2'-dicarboxylate dianion (bpdc^2-) and a coordinated water molecule.

The Cu^II atom is six-coordinated by two N atoms from bpy and four O atoms, three from two bpdc^2- anions and one from coordinated H₂O, in a distorted octahedron coordination geometry. And it is noteworthy that the two Cu^II ions in the complex are bridged by two bpdc^2- dianions, one is in a bis-monodentate mode whereas the other is in a bis-bidentate mode.

Related literature top

For related structures, see: Li et al. (2009); Jiang & Feng (2009); Xu et al. (2009); Zhang et al. (2009); Rizal & Ng (2009); Zhang (2009).

Experimental top

The title complound was synthesized hydrothermally in a Teflon-lined autoclave (25 ml) by heating a mixture of H₂bpdc (0.2 mmol), dbpy (0.4 mmol) and CuSO₄.5H₂O (0.2 mmol) in water (10 ml) at 393 K for 3 d. Crystals suitable for X-ray analysis were obtained.

Structure description top

For related structures, see: Li et al. (2009); Jiang & Feng (2009); Xu et al. (2009); Zhang et al. (2009); Rizal & Ng (2009); Zhang (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius. Hydrogen-bond interactions are drawn with dashed lines. Atoms labeled(i) are generated by the symmetry code -x, y, -z + 1/2.

Bis(µ-biphenyl-2,2'-dicarboxylato)bis[aqua(4,4'-dimethyl-2,2'- bipyridine)copper(II)] top

Crystal data top

[Cu₂(C₁₄H₈O₄)₂(C₁₂H₁₂N₂)₂(H₂O)₂]	F(000) = 2240
M_r = 1109.71	D_x = 1.580 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3688 reflections
a = 17.104 (3) Å	θ = 2.7–27.3°
b = 15.395 (2) Å	µ = 0.98 mm⁻¹
c = 18.289 (3) Å	T = 296 K
β = 104.413 (3)°	Block, colourless
V = 4664.2 (13) Å³	0.26 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4594 independent reflections
Radiation source: fine-focus sealed tube	3108 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→20
T_min = 0.785, T_max = 0.814	k = −18→12
13512 measured reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
4594 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 0.87 e Å⁻³
12 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Cu₂(C₁₄H₈O₄)₂(C₁₂H₁₂N₂)₂(H₂O)₂]	V = 4664.2 (13) Å³
M_r = 1109.71	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.104 (3) Å	µ = 0.98 mm⁻¹
b = 15.395 (2) Å	T = 296 K
c = 18.289 (3) Å	0.26 × 0.24 × 0.22 mm
β = 104.413 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4594 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3108 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.814	R_int = 0.060
13512 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	12 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	Δρ_max = 0.87 e Å⁻³
4594 reflections	Δρ_min = −0.33 e Å⁻³
310 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
Cd1	0.13088 (2)	0.599652 (19)	0.344239 (17)	0.05361 (14)
N1	0.1810 (2)	0.5542 (2)	0.4686 (2)	0.0615 (10)
N2	0.2592 (2)	0.6574 (2)	0.39215 (19)	0.0516 (9)
O1	0.11652 (18)	0.67905 (18)	0.23068 (16)	0.0602 (8)
O2	0.0871 (2)	0.74927 (19)	0.32546 (17)	0.0611 (8)
O3	0.1387 (2)	0.4729 (2)	0.2927 (3)	0.0977 (12)
O4	0.0538 (2)	0.41826 (19)	0.1917 (2)	0.0701 (10)
O1W	0.00362 (18)	0.57274 (19)	0.35468 (17)	0.0611 (8)
H1WA	−0.0326	0.6100	0.3365	0.073*
H1WB	−0.0137	0.5234	0.3371	0.073*
C1	0.0942 (3)	0.7474 (3)	0.2590 (3)	0.0527 (11)
C2	0.0782 (3)	0.8273 (3)	0.2111 (2)	0.0537 (11)
C3	0.1193 (3)	0.8370 (3)	0.1546 (3)	0.0677 (14)
H3	0.1545	0.7937	0.1473	0.081*
C4	0.1087 (4)	0.9095 (3)	0.1096 (3)	0.0825 (17)
H4	0.1387	0.9161	0.0740	0.099*
C5	0.0541 (4)	0.9725 (3)	0.1166 (3)	0.0813 (16)
H5	0.0455	1.0205	0.0848	0.098*
C6	0.0121 (3)	0.9632 (3)	0.1716 (3)	0.0685 (14)
H6	−0.0245	1.0060	0.1769	0.082*
C7	0.0232 (3)	0.8913 (2)	0.2195 (3)	0.0540 (11)
C8	0.0959 (3)	0.4138 (3)	0.2577 (4)	0.0675 (15)
C9	0.0975 (3)	0.3293 (3)	0.3005 (3)	0.0578 (12)
C10	0.1638 (4)	0.3135 (4)	0.3615 (4)	0.0935 (19)
H10	0.2047	0.3546	0.3747	0.112*
C11	0.1687 (5)	0.2361 (5)	0.4026 (4)	0.114 (2)
H11	0.2144	0.2245	0.4411	0.137*
C12	0.1072 (5)	0.1780 (4)	0.3865 (4)	0.101 (2)
H12	0.1096	0.1276	0.4151	0.121*
C13	0.0428 (3)	0.1938 (3)	0.3290 (3)	0.0691 (14)
H13	0.0007	0.1538	0.3194	0.083*
C14	0.0357 (3)	0.2671 (2)	0.2827 (2)	0.0491 (10)
C15	0.2960 (3)	0.7114 (3)	0.3534 (2)	0.0619 (12)
H15	0.2725	0.7195	0.3023	0.074*
C16	0.3658 (3)	0.7551 (3)	0.3848 (3)	0.0577 (12)
H16	0.3882	0.7925	0.3556	0.069*
C17	0.4026 (3)	0.7432 (3)	0.4598 (2)	0.0523 (11)
C18	0.3652 (3)	0.6872 (3)	0.4998 (2)	0.0514 (11)
H18	0.3882	0.6778	0.5508	0.062*
C19	0.2946 (3)	0.6456 (2)	0.4655 (2)	0.0446 (10)
C20	0.2522 (3)	0.5850 (2)	0.5076 (3)	0.0484 (11)
C21	0.2842 (3)	0.5611 (3)	0.5819 (3)	0.0575 (12)
H21	0.3336	0.5840	0.6080	0.069*
C22	0.2441 (3)	0.5040 (3)	0.6179 (3)	0.0589 (12)
C23	0.1719 (3)	0.4713 (3)	0.5762 (3)	0.0750 (15)
H23	0.1435	0.4311	0.5974	0.090*
C24	0.1423 (3)	0.4981 (3)	0.5035 (3)	0.0761 (15)
H24	0.0927	0.4763	0.4766	0.091*
C25	0.4800 (3)	0.7895 (3)	0.4962 (3)	0.0717 (14)
H25A	0.4703	0.8509	0.4960	0.108*
H25B	0.5196	0.7774	0.4685	0.108*
H25C	0.4994	0.7698	0.5473	0.108*
C26	0.2776 (3)	0.4777 (4)	0.6985 (3)	0.0843 (16)
H26A	0.3136	0.4294	0.7006	0.126*
H26B	0.2342	0.4612	0.7203	0.126*
H26C	0.3066	0.5256	0.7263	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0639 (3)	0.0397 (2)	0.0639 (2)	−0.00834 (15)	0.02867 (18)	−0.00204 (16)
N1	0.068 (3)	0.050 (2)	0.073 (3)	−0.012 (2)	0.031 (2)	0.012 (2)
N2	0.062 (2)	0.044 (2)	0.057 (2)	−0.0098 (17)	0.0290 (18)	0.0006 (17)
O1	0.074 (2)	0.0420 (17)	0.073 (2)	0.0006 (15)	0.0356 (17)	−0.0078 (15)
O2	0.078 (2)	0.0476 (17)	0.068 (2)	0.0056 (15)	0.0378 (17)	0.0039 (15)
O3	0.087 (2)	0.070 (2)	0.150 (3)	−0.021 (2)	0.057 (2)	−0.040 (2)
O4	0.084 (3)	0.0377 (18)	0.106 (3)	−0.0016 (17)	0.058 (2)	−0.0019 (19)
O1W	0.065 (2)	0.0444 (16)	0.080 (2)	−0.0043 (15)	0.0306 (17)	−0.0008 (16)
C1	0.055 (3)	0.039 (2)	0.073 (3)	−0.0036 (19)	0.033 (2)	0.001 (2)
C2	0.063 (3)	0.042 (2)	0.065 (3)	−0.007 (2)	0.032 (2)	−0.002 (2)
C3	0.082 (4)	0.054 (3)	0.080 (3)	−0.004 (3)	0.045 (3)	0.003 (3)
C4	0.113 (5)	0.073 (4)	0.078 (4)	−0.014 (3)	0.054 (3)	0.009 (3)
C5	0.115 (5)	0.050 (3)	0.087 (4)	−0.005 (3)	0.040 (3)	0.017 (3)
C6	0.088 (4)	0.041 (3)	0.083 (3)	−0.002 (2)	0.035 (3)	0.008 (2)
C7	0.063 (3)	0.035 (2)	0.068 (3)	−0.005 (2)	0.025 (2)	0.000 (2)
C8	0.062 (3)	0.044 (3)	0.116 (5)	−0.009 (2)	0.057 (3)	−0.029 (3)
C9	0.058 (3)	0.053 (3)	0.069 (3)	0.005 (2)	0.027 (2)	−0.026 (2)
C10	0.067 (4)	0.093 (5)	0.117 (5)	0.003 (3)	0.017 (4)	−0.044 (4)
C11	0.116 (5)	0.116 (5)	0.093 (4)	0.045 (5)	−0.008 (4)	−0.020 (4)
C12	0.125 (6)	0.089 (5)	0.082 (4)	0.030 (4)	0.013 (4)	−0.001 (4)
C13	0.090 (4)	0.052 (3)	0.069 (3)	0.017 (3)	0.026 (3)	0.003 (3)
C14	0.061 (3)	0.035 (2)	0.058 (3)	0.0070 (19)	0.0269 (19)	−0.0053 (19)
C15	0.072 (3)	0.065 (3)	0.055 (3)	−0.009 (3)	0.029 (2)	0.012 (2)
C16	0.066 (3)	0.049 (3)	0.068 (3)	−0.010 (2)	0.037 (3)	0.008 (2)
C17	0.066 (3)	0.036 (2)	0.065 (3)	−0.003 (2)	0.036 (2)	−0.004 (2)
C18	0.062 (3)	0.047 (2)	0.052 (2)	−0.003 (2)	0.027 (2)	−0.003 (2)
C19	0.056 (3)	0.032 (2)	0.055 (3)	0.0018 (19)	0.031 (2)	−0.0006 (19)
C20	0.056 (3)	0.036 (2)	0.062 (3)	0.0020 (19)	0.032 (2)	0.001 (2)
C21	0.066 (3)	0.052 (3)	0.064 (3)	−0.001 (2)	0.034 (2)	0.008 (2)
C22	0.069 (3)	0.054 (3)	0.068 (3)	0.006 (2)	0.042 (3)	0.010 (2)
C23	0.083 (4)	0.068 (3)	0.087 (4)	−0.013 (3)	0.045 (3)	0.025 (3)
C24	0.068 (3)	0.070 (3)	0.096 (4)	−0.016 (3)	0.030 (3)	0.020 (3)
C25	0.077 (4)	0.068 (3)	0.077 (3)	−0.023 (3)	0.033 (3)	−0.007 (3)
C26	0.106 (4)	0.083 (4)	0.079 (4)	−0.003 (3)	0.050 (3)	0.022 (3)

Geometric parameters (Å, º) top

Cd1—O3	2.186 (4)	C10—H10	0.9300
Cd1—O1W	2.270 (3)	C11—C12	1.357 (9)
Cd1—N2	2.327 (3)	C11—H11	0.9300
Cd1—N1	2.329 (4)	C12—C13	1.342 (8)
Cd1—O1	2.369 (3)	C12—H12	0.9300
Cd1—O2	2.420 (3)	C13—C14	1.397 (6)
N1—C20	1.335 (6)	C13—H13	0.9300
N1—C24	1.343 (5)	C14—C14ⁱ	1.482 (8)
N2—C19	1.339 (5)	C15—C16	1.366 (6)
N2—C15	1.346 (5)	C15—H15	0.9300
O1—C1	1.272 (5)	C16—C17	1.371 (6)
O2—C1	1.252 (5)	C16—H16	0.9300
O3—C8	1.240 (6)	C17—C18	1.386 (5)
O4—C8	1.244 (6)	C17—C25	1.505 (6)
O1W—H1WA	0.8498	C18—C19	1.373 (6)
O1W—H1WB	0.8499	C18—H18	0.9300
C1—C2	1.495 (6)	C19—C20	1.506 (5)
C2—C3	1.395 (6)	C20—C21	1.382 (6)
C2—C7	1.397 (6)	C21—C22	1.380 (6)
C3—C4	1.372 (6)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.375 (7)
C4—C5	1.374 (7)	C22—C26	1.499 (6)
C4—H4	0.9300	C23—C24	1.364 (7)
C5—C6	1.382 (7)	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.394 (6)	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C7—C7ⁱ	1.524 (8)	C25—H25C	0.9600
C8—C9	1.515 (7)	C26—H26A	0.9600
C9—C10	1.400 (8)	C26—H26B	0.9600
C9—C14	1.403 (6)	C26—H26C	0.9600
C10—C11	1.400 (9)

O3—Cd1—O1W	92.06 (12)	C9—C10—H10	119.9
O3—Cd1—N2	110.50 (13)	C12—C11—C10	120.3 (6)
O1W—Cd1—N2	150.70 (11)	C12—C11—H11	119.8
O3—Cd1—N1	96.06 (15)	C10—C11—H11	119.8
O1W—Cd1—N1	89.48 (12)	C13—C12—C11	119.4 (6)
N2—Cd1—N1	70.32 (12)	C13—C12—H12	120.3
O3—Cd1—O1	95.00 (13)	C11—C12—H12	120.3
O1W—Cd1—O1	106.00 (11)	C12—C13—C14	123.5 (6)
N2—Cd1—O1	90.88 (11)	C12—C13—H13	118.2
N1—Cd1—O1	160.61 (12)	C14—C13—H13	118.2
O3—Cd1—O2	147.01 (15)	C13—C14—C9	117.6 (4)
O1W—Cd1—O2	85.21 (10)	C13—C14—C14ⁱ	114.8 (4)
N2—Cd1—O2	85.37 (12)	C9—C14—C14ⁱ	127.5 (3)
N1—Cd1—O2	116.74 (12)	N2—C15—C16	123.9 (4)
O1—Cd1—O2	54.80 (9)	N2—C15—H15	118.0
C20—N1—C24	117.8 (4)	C16—C15—H15	118.0
C20—N1—Cd1	118.7 (3)	C15—C16—C17	119.3 (4)
C24—N1—Cd1	123.5 (4)	C15—C16—H16	120.4
C19—N2—C15	117.1 (4)	C17—C16—H16	120.4
C19—N2—Cd1	118.3 (2)	C16—C17—C18	117.0 (4)
C15—N2—Cd1	124.0 (3)	C16—C17—C25	120.9 (4)
C1—O1—Cd1	92.7 (2)	C18—C17—C25	122.1 (4)
C1—O2—Cd1	90.8 (2)	C19—C18—C17	121.2 (4)
C8—O3—Cd1	141.8 (3)	C19—C18—H18	119.4
Cd1—O1W—H1WA	117.7	C17—C18—H18	119.4
Cd1—O1W—H1WB	112.5	N2—C19—C18	121.5 (4)
H1WA—O1W—H1WB	107.7	N2—C19—C20	116.1 (4)
O2—C1—O1	121.7 (4)	C18—C19—C20	122.4 (4)
O2—C1—C2	120.2 (4)	N1—C20—C21	121.1 (4)
O1—C1—C2	118.1 (4)	N1—C20—C19	115.9 (4)
C3—C2—C7	118.8 (4)	C21—C20—C19	123.0 (4)
C3—C2—C1	118.0 (4)	C22—C21—C20	121.1 (5)
C7—C2—C1	123.1 (4)	C22—C21—H21	119.5
C4—C3—C2	121.1 (5)	C20—C21—H21	119.5
C4—C3—H3	119.5	C23—C22—C21	116.9 (4)
C2—C3—H3	119.5	C23—C22—C26	121.2 (4)
C3—C4—C5	120.7 (5)	C21—C22—C26	121.9 (5)
C3—C4—H4	119.7	C24—C23—C22	119.7 (4)
C5—C4—H4	119.7	C24—C23—H23	120.2
C4—C5—C6	119.0 (5)	C22—C23—H23	120.2
C4—C5—H5	120.5	N1—C24—C23	123.4 (5)
C6—C5—H5	120.5	N1—C24—H24	118.3
C5—C6—C7	121.6 (5)	C23—C24—H24	118.3
C5—C6—H6	119.2	C17—C25—H25A	109.5
C7—C6—H6	119.2	C17—C25—H25B	109.5
C6—C7—C2	118.8 (4)	H25A—C25—H25B	109.5
C6—C7—C7ⁱ	116.4 (3)	C17—C25—H25C	109.5
C2—C7—C7ⁱ	124.6 (3)	H25A—C25—H25C	109.5
O3—C8—O4	125.9 (6)	H25B—C25—H25C	109.5
O3—C8—C9	115.5 (6)	C22—C26—H26A	109.5
O4—C8—C9	118.7 (4)	C22—C26—H26B	109.5
C10—C9—C14	118.7 (5)	H26A—C26—H26B	109.5
C10—C9—C8	117.9 (5)	C22—C26—H26C	109.5
C14—C9—C8	123.5 (4)	H26A—C26—H26C	109.5
C11—C10—C9	120.3 (6)	H26B—C26—H26C	109.5
C11—C10—H10	119.9

O3—Cd1—N1—C20	113.7 (3)	C1—C2—C7—C6	−179.5 (4)
O1W—Cd1—N1—C20	−154.3 (3)	C3—C2—C7—C7ⁱ	−177.3 (5)
N2—Cd1—N1—C20	4.0 (3)	C1—C2—C7—C7ⁱ	3.9 (8)
O1—Cd1—N1—C20	−10.8 (6)	Cd1—O3—C8—O4	69.7 (8)
O2—Cd1—N1—C20	−69.9 (3)	Cd1—O3—C8—C9	−111.2 (6)
O3—Cd1—N1—C24	−65.9 (4)	O3—C8—C9—C10	−21.7 (6)
O1W—Cd1—N1—C24	26.1 (4)	O4—C8—C9—C10	157.6 (4)
N2—Cd1—N1—C24	−175.6 (4)	O3—C8—C9—C14	157.5 (4)
O1—Cd1—N1—C24	169.6 (3)	O4—C8—C9—C14	−23.3 (6)
O2—Cd1—N1—C24	110.5 (4)	C14—C9—C10—C11	1.4 (7)
O3—Cd1—N2—C19	−95.8 (3)	C8—C9—C10—C11	−179.4 (5)
O1W—Cd1—N2—C19	42.3 (4)	C9—C10—C11—C12	−3.8 (10)
N1—Cd1—N2—C19	−6.6 (3)	C10—C11—C12—C13	2.4 (10)
O1—Cd1—N2—C19	168.5 (3)	C11—C12—C13—C14	1.3 (9)
O2—Cd1—N2—C19	114.0 (3)	C12—C13—C14—C9	−3.6 (7)
O3—Cd1—N2—C15	93.2 (4)	C12—C13—C14—C14ⁱ	173.3 (5)
O1W—Cd1—N2—C15	−128.7 (3)	C10—C9—C14—C13	2.1 (6)
N1—Cd1—N2—C15	−177.6 (4)	C8—C9—C14—C13	−177.0 (4)
O1—Cd1—N2—C15	−2.5 (3)	C10—C9—C14—C14ⁱ	−174.3 (5)
O2—Cd1—N2—C15	−57.1 (3)	C8—C9—C14—C14ⁱ	6.5 (7)
O3—Cd1—O1—C1	166.2 (3)	C19—N2—C15—C16	−1.0 (7)
O1W—Cd1—O1—C1	72.6 (3)	Cd1—N2—C15—C16	170.2 (4)
N2—Cd1—O1—C1	−83.1 (3)	N2—C15—C16—C17	1.1 (7)
N1—Cd1—O1—C1	−69.2 (4)	C15—C16—C17—C18	−0.7 (6)
O2—Cd1—O1—C1	0.6 (2)	C15—C16—C17—C25	179.5 (4)
O3—Cd1—O2—C1	−27.6 (4)	C16—C17—C18—C19	0.2 (6)
O1W—Cd1—O2—C1	−114.0 (3)	C25—C17—C18—C19	−180.0 (4)
N2—Cd1—O2—C1	93.8 (3)	C15—N2—C19—C18	0.4 (6)
N1—Cd1—O2—C1	159.0 (3)	Cd1—N2—C19—C18	−171.2 (3)
O1—Cd1—O2—C1	−0.6 (2)	C15—N2—C19—C20	179.9 (4)
O1W—Cd1—O3—C8	22.1 (7)	Cd1—N2—C19—C20	8.3 (4)
N2—Cd1—O3—C8	−177.0 (7)	C17—C18—C19—N2	−0.1 (6)
N1—Cd1—O3—C8	111.8 (7)	C17—C18—C19—C20	−179.5 (4)
O1—Cd1—O3—C8	−84.2 (7)	C24—N1—C20—C21	−1.3 (6)
O2—Cd1—O3—C8	−62.3 (8)	Cd1—N1—C20—C21	179.0 (3)
Cd1—O2—C1—O1	1.1 (4)	C24—N1—C20—C19	178.2 (4)
Cd1—O2—C1—C2	−177.5 (4)	Cd1—N1—C20—C19	−1.4 (5)
Cd1—O1—C1—O2	−1.1 (4)	N2—C19—C20—N1	−4.5 (5)
Cd1—O1—C1—C2	177.5 (3)	C18—C19—C20—N1	175.0 (4)
O2—C1—C2—C3	151.3 (4)	N2—C19—C20—C21	175.0 (4)
O1—C1—C2—C3	−27.4 (6)	C18—C19—C20—C21	−5.5 (6)
O2—C1—C2—C7	−29.9 (7)	N1—C20—C21—C22	0.8 (6)
O1—C1—C2—C7	151.5 (4)	C19—C20—C21—C22	−178.7 (4)
C7—C2—C3—C4	2.4 (8)	C20—C21—C22—C23	1.0 (7)
C1—C2—C3—C4	−178.7 (5)	C20—C21—C22—C26	−179.8 (4)
C2—C3—C4—C5	−3.3 (8)	C21—C22—C23—C24	−2.1 (7)
C3—C4—C5—C6	2.4 (9)	C26—C22—C23—C24	178.6 (5)
C4—C5—C6—C7	−0.7 (9)	C20—N1—C24—C23	0.1 (7)
C5—C6—C7—C2	−0.1 (8)	Cd1—N1—C24—C23	179.7 (4)
C5—C6—C7—C7ⁱ	176.7 (5)	C22—C23—C24—N1	1.7 (8)
C3—C2—C7—C6	−0.7 (7)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O4ⁱ	0.85	1.78	2.632 (4)	174
O1W—H1WA···O1ⁱ	0.85	1.95	2.782 (4)	164

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₄H₈O₄)₂(C₁₂H₁₂N₂)₂(H₂O)₂]
M_r	1109.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	17.104 (3), 15.395 (2), 18.289 (3)
β (°)	104.413 (3)
V (Å³)	4664.2 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.785, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	13512, 4594, 3108
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 0.93
No. of reflections	4594
No. of parameters	310
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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—H1WB···O4ⁱ	0.85	1.78	2.632 (4)	174.3
O1W—H1WA···O1ⁱ	0.85	1.95	2.782 (4)	164.4

Symmetry code: (i) −x, y, −z+1/2.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiang, M.-X. & Feng, Y.-L. (2009). Acta Cryst. E65, m654. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, F., Zeng, H., Yan, Z. & Li, T. (2009). Acta Cryst. E65, m681. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rizal, M. R. & Ng, S. W. (2009). Acta Cryst. E65, m1178. 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
Xu, B.-Y., Xie, T., Lu, S.-J., Xue, B. & Li, W. (2009). Acta Cryst. E65, m856–m857. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Zhang, L. (2009). Acta Cryst. E65, m871–m872. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, J., Chen, X.-D., Zhang, H.-H. & Sun, B.-W. (2009). Acta Cryst. E65, m1136. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page m1360

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