[μ2-N2,N2′-Bis(3-meth­oxy-2-oxido­benzyl­idene)benzene-1,3-dicarbo­hydrazi­dato]bis­[pyridine­copper(II)]

Tong, H.-B.; Xiao, Z.-J.

doi:10.1107/S1600536813030286

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page m658

doi:10.1107/S1600536813030286

Open

access

[μ₂-N²,N^2′-Bis(3-methoxy-2-oxidobenzylidene)benzene-1,3-dicarbohydrazidato]bis[pyridinecopper(II)]

Hai-Bin Tong ^a and Zi-Jing Xiao ^a ^*

^aCollege of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021, People's Republic of China
^*Correspondence e-mail: xzj@hqu.edu.cn

(Received 21 October 2013; accepted 5 November 2013; online 13 November 2013)

In the centrosymmetric dinuclear title complex, [Cu₂(C₂₄H₁₈N₄O₆)(C₅H₅N)₂], the Cu^II ions is tetracoordinated by two O-atoms and one N-donor of the bridging terephthalohydrazonate ligand and by one pyridine N atom, resulting in a nearly square-planar N₂O₂ coordination geometry with the Cu^II ion 0.044 (2) Å out of the mean plane (r.m.s. deviation of 0.0675 Å) of the coordinating atoms.

CCDC reference: 970316

Related literature

For the structural coordination chemistry and potential applications in luminescence, redox activity and magnetism of bifunctional organic ligands and their complexes, see: He et al. (2004 ); Qiao et al. (2007 ); Yin et al. (2008 ); Zhu et al. (2010 ); Lin et al. (2012 ). For the crystal structures of dinuclear copper(II) complexes with a similar coordination geometry, see: Banerjee et al. (2009 ); Shulgin et al. (2011 ); Mistri et al. (2013 ). For the synthesis of N,N′-bis(3-methoxy-2-oxybenzylidene)terephthalohydrazone, see: Yin et al. (2008).

Experimental

Crystal data

[Cu₂(C₂₄H₁₈N₄O₆)(C₅H₅N)₂]
M_r = 743.70
Monoclinic, P 2₁ /n
a = 4.8474 (2) Å
b = 15.2776 (6) Å
c = 20.5546 (6) Å
β = 96.113 (4)°
V = 1513.55 (10) Å³
Z = 2
Cu Kα radiation
μ = 2.23 mm⁻¹
T = 153 K
0.45 × 0.32 × 0.22 mm

Data collection

Agilent Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.447, T_max = 0.615
5837 measured reflections
2658 independent reflections
2113 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.133
S = 1.06
2658 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 970316

Crystal structure: contains datablocks I, a. DOI: 10.1107/S1600536813030286/fj2648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030286/fj2648Isup2.hkl

checkCIF report

Comment top

Bifunctional organic ligand and their complexes have attracted increasing interest in recent years, due to their potential applications in luminescence, redox activity, magnetism and diversities of coordination (He et al., 2004; Qiao et al., 2007; Yin et al., 2008; Zhu et al., 2010; Lin et al., 2012). Relatively speaking, only a few crystal structures of arylaldehyde terephthalohydrazone complexes have been reported (He et al., 2004; Yin et al.,2008; Lin et al., 2012). Herein, we report the synthesis and structure of copper complex with N,N'-bis(3-methoxy-2-oxybenzylidene)terephthalohydrazone.

As show in Fig 1, we can see that the title complex contain dinuclear copper(II) skeletons showing a trans conformation (centrosymmetry). That is, one half of the dinuclear copper(II) complex constitutes the crystallographic asymmetric unit and the other half is produced by an inversion centre. In the title complex, Cu1(II) ion is coordinated by carbonyl atom O1, hydrazine atom N2 and phenol atom O2 from the moieties of the ligand H₄L, which is hexadentate ligand that function as tetrabasic in the enol form, and N3 atom from coordinated pyridine molecule, obtaining a nearly square-planar N₂O₂ geometry (r.m.s deviation =0.0675 Å). The Cu^II atom is shifted 0.044 (2) Å out of the square-plane. One five-membered chelate ring (ring M₁) and one six-membered chelate ring (ring M₂) are formed by the moieties of the ligand L^4- and Cu1 atom. The ring M₁ is composed of Cu1, N2, N1, C1 and O1 with r.m.s deviation of 0.0123 Å,The ring M₂ of Cu1, N2, C5, C6, C7 and O2 with r.m.s deviation of 0.0238 Å. All two chelate rings are planar. The bond lengths of Cu—N and Cu—O in the title complex are similar to those in other dinuclear copper(II) complexes (Banerjee et al., 2009; Shulgin et al., 2011; Mistri et al., 2013). The whole L^4- ligand is a nearly planar (r.m.s deviation=0.0805 Å), the dihedral angle between the two benzene rings is 7.29 (29)°.

Related literature top

For the structural coordination chemistry and potential applications in luminescence, redox activity and magnetism of bifunctional organic ligands and their complexes, see: He et al. (2004); Qiao et al. (2007); Yin et al. (2008); Zhu et al. (2010); Lin et al. (2012). For the crystal structures of dinuclear copper(II) complexes with a similar coordination geometry, see: Banerjee et al. (2009); Shulgin et al. (2011); Mistri et al. (2013). For the synthesis of N,N'-bis(3-methoxy-2-oxybenzylidene)terephthalohydrazone, see: Yin et al. (2008).

Experimental top

Reagents and solvents were used as obtained without further purification. N,N'-bis(3-methoxy-2-oxybenzylidene)terephthalohydrazone (H₄L) was synthesized according to the literature methods (Yin et al., 2008). H₄L (0.0462 g, 0.1 mmol) and copper(II) chloride dihydrate (0.0342 g, 0.2 mmol) were dissolved in a mixed solution of 10 ml CH₃OH and 5 ml DMF. The mixture was stirred for 10 minutes at room temperature and then 5 ml pyridine was slowly added. The reaction mixture was further stirred for 4 h. After being obtained by filtration, the dark green filtrate was allowed to stand at room temperature for 15 days. The dark green prism crystals of the title complex were obtained by slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title complex, showing 50% probability displacement ellipsoids and the atom numbering scheme.

[µ₂-N²,N^2'-Bis(3-methoxy-2-oxidobenzylidene)benzene-1,3-dicarbohydrazidato]bis[pyridinecopper(II)] top

Crystal data top

[Cu₂(C₂₄H₁₈N₄O₆)(C₅H₅N)₂]	F(000) = 760
M_r = 743.70	D_x = 1.632 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2658 reflections
a = 4.8474 (2) Å	θ = 3.6–66.5°
b = 15.2776 (6) Å	µ = 2.23 mm⁻¹
c = 20.5546 (6) Å	T = 153 K
β = 96.113 (4)°	Prism, dark green
V = 1513.55 (10) Å³	0.45 × 0.32 × 0.22 mm
Z = 2

Data collection top

Agilent Gemini S Ultra diffractometer	2658 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2113 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 15.9149 pixels mm^-1	θ_max = 66.5°, θ_min = 3.6°
ω scans	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→17
T_min = 0.447, T_max = 0.615	l = −24→24
5837 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0637P)² + 0.5957P] where P = (F_o² + 2F_c²)/3
2658 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Cu₂(C₂₄H₁₈N₄O₆)(C₅H₅N)₂]	V = 1513.55 (10) Å³
M_r = 743.70	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.8474 (2) Å	µ = 2.23 mm⁻¹
b = 15.2776 (6) Å	T = 153 K
c = 20.5546 (6) Å	0.45 × 0.32 × 0.22 mm
β = 96.113 (4)°

Data collection top

Agilent Gemini S Ultra diffractometer	2658 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2113 reflections with I > 2σ(I)
T_min = 0.447, T_max = 0.615	R_int = 0.029
5837 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
2658 reflections	Δρ_min = −0.35 e Å⁻³
218 parameters

Special details top

Experimental. CrysAlis PRO, Agilent Technologies, Version 1.171.36.21 (release 14–08-2012 CrysAlis171. NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cu1	0.10363 (10)	0.25720 (3)	0.16238 (2)	0.0517 (2)
N1	0.0548 (6)	0.3121 (2)	0.03092 (13)	0.0562 (7)
N2	−0.0561 (6)	0.25260 (18)	0.07303 (14)	0.0508 (7)
N3	0.2965 (6)	0.26684 (19)	0.25349 (14)	0.0511 (7)
O1	0.3097 (5)	0.35162 (17)	0.12788 (10)	0.0565 (6)
O2	−0.1445 (5)	0.17419 (17)	0.19006 (11)	0.0602 (6)
O3	−0.4238 (6)	0.0629 (2)	0.25128 (12)	0.0706 (8)
C1	0.2389 (7)	0.3600 (2)	0.06565 (16)	0.0511 (8)
C2	0.3731 (7)	0.4314 (2)	0.03120 (16)	0.0528 (8)
C3	0.3252 (9)	0.4435 (3)	−0.03547 (17)	0.0730 (12)
H3A	0.2067	0.4054	−0.0603	0.088*
C4	0.5515 (9)	0.4894 (3)	0.06609 (18)	0.0733 (12)
H4A	0.5884	0.4828	0.1112	0.088*
C5	−0.2521 (8)	0.2022 (3)	0.04869 (17)	0.0578 (9)
H5A	−0.3074	0.2070	0.0041	0.069*
C6	−0.3922 (7)	0.1392 (2)	0.08483 (17)	0.0541 (8)
C7	−0.3333 (7)	0.1298 (2)	0.15349 (17)	0.0530 (8)
C8	−0.4884 (8)	0.0671 (3)	0.18484 (18)	0.0564 (9)
C9	−0.6886 (8)	0.0168 (3)	0.1499 (2)	0.0666 (10)
H9A	−0.7900	−0.0235	0.1715	0.080*
C10	−0.7394 (8)	0.0262 (3)	0.0824 (2)	0.0684 (11)
H10A	−0.8718	−0.0088	0.0589	0.082*
C11	−0.5966 (8)	0.0862 (3)	0.05070 (19)	0.0643 (10)
H11A	−0.6343	0.0924	0.0056	0.077*
C12	−0.5910 (10)	0.0070 (3)	0.2862 (2)	0.0793 (13)
H12A	−0.5422	0.0145	0.3324	0.119*
H12B	−0.5606	−0.0528	0.2745	0.119*
H12C	−0.7830	0.0216	0.2753	0.119*
C13	0.5123 (8)	0.3210 (2)	0.26756 (17)	0.0571 (9)
H13A	0.5736	0.3542	0.2340	0.069*
C14	0.6461 (8)	0.3293 (3)	0.32932 (19)	0.0648 (10)
H14A	0.7951	0.3675	0.3373	0.078*
C15	0.5587 (9)	0.2807 (3)	0.37955 (19)	0.0665 (10)
H15A	0.6463	0.2857	0.4219	0.080*
C16	0.3409 (9)	0.2250 (3)	0.36585 (18)	0.0651 (10)
H16A	0.2792	0.1908	0.3988	0.078*
C17	0.2124 (8)	0.2198 (3)	0.30282 (17)	0.0583 (9)
H17A	0.0619	0.1823	0.2942	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0608 (3)	0.0568 (3)	0.0367 (3)	−0.0049 (2)	0.0017 (2)	0.0011 (2)
N1	0.0682 (18)	0.0619 (18)	0.0379 (14)	−0.0119 (15)	0.0030 (13)	0.0058 (14)
N2	0.0598 (16)	0.0557 (17)	0.0365 (14)	−0.0046 (14)	0.0035 (12)	0.0003 (12)
N3	0.0583 (16)	0.0568 (17)	0.0377 (14)	0.0027 (14)	0.0026 (12)	0.0013 (13)
O1	0.0745 (15)	0.0598 (14)	0.0348 (11)	−0.0132 (12)	0.0035 (10)	0.0020 (10)
O2	0.0668 (15)	0.0699 (16)	0.0429 (12)	−0.0143 (13)	0.0011 (11)	0.0015 (12)
O3	0.0825 (18)	0.0779 (18)	0.0502 (14)	−0.0214 (15)	0.0014 (13)	0.0066 (13)
C1	0.061 (2)	0.0542 (19)	0.0382 (16)	0.0007 (16)	0.0072 (14)	0.0010 (15)
C2	0.064 (2)	0.0564 (19)	0.0377 (16)	−0.0036 (17)	0.0056 (14)	0.0031 (15)
C3	0.093 (3)	0.084 (3)	0.0399 (18)	−0.037 (2)	−0.0064 (18)	0.0040 (19)
C4	0.098 (3)	0.084 (3)	0.0352 (17)	−0.032 (2)	−0.0025 (18)	0.0083 (19)
C5	0.065 (2)	0.069 (2)	0.0384 (17)	−0.0003 (19)	0.0012 (15)	0.0005 (17)
C6	0.0566 (19)	0.056 (2)	0.0488 (19)	0.0008 (16)	0.0015 (15)	−0.0029 (16)
C7	0.0555 (18)	0.055 (2)	0.0479 (18)	−0.0001 (16)	0.0034 (15)	−0.0024 (16)
C8	0.061 (2)	0.055 (2)	0.053 (2)	−0.0017 (17)	0.0044 (16)	−0.0002 (17)
C9	0.063 (2)	0.066 (2)	0.070 (3)	−0.0103 (19)	0.0030 (19)	0.003 (2)
C10	0.066 (2)	0.069 (2)	0.067 (3)	−0.013 (2)	−0.0083 (19)	−0.004 (2)
C11	0.067 (2)	0.068 (2)	0.054 (2)	−0.004 (2)	−0.0074 (17)	−0.0025 (19)
C12	0.099 (3)	0.077 (3)	0.061 (2)	−0.025 (3)	0.008 (2)	0.011 (2)
C13	0.062 (2)	0.059 (2)	0.0490 (19)	−0.0002 (18)	0.0022 (16)	0.0064 (17)
C14	0.062 (2)	0.068 (2)	0.062 (2)	−0.0012 (19)	−0.0088 (18)	−0.005 (2)
C15	0.074 (2)	0.080 (3)	0.0429 (19)	0.009 (2)	−0.0090 (17)	−0.0009 (19)
C16	0.080 (3)	0.073 (3)	0.0418 (19)	0.001 (2)	0.0011 (18)	0.0078 (18)
C17	0.067 (2)	0.063 (2)	0.0446 (19)	−0.0036 (18)	0.0009 (16)	0.0065 (17)

Geometric parameters (Å, º) top

Cu1—O2	1.877 (3)	C6—C11	1.407 (5)
Cu1—N2	1.917 (3)	C6—C7	1.417 (5)
Cu1—O1	1.932 (2)	C7—C8	1.414 (5)
Cu1—N3	2.007 (3)	C8—C9	1.379 (5)
N1—C1	1.307 (5)	C9—C10	1.389 (5)
N1—N2	1.401 (4)	C9—H9A	0.9300
N2—C5	1.282 (5)	C10—C11	1.357 (5)
N3—C13	1.341 (5)	C10—H10A	0.9300
N3—C17	1.341 (5)	C11—H11A	0.9300
O1—C1	1.295 (4)	C12—H12A	0.9600
O2—C7	1.310 (4)	C12—H12B	0.9600
O3—C8	1.370 (4)	C12—H12C	0.9600
O3—C12	1.423 (4)	C13—C14	1.368 (5)
C1—C2	1.487 (5)	C13—H13A	0.9300
C2—C3	1.378 (5)	C14—C15	1.375 (6)
C2—C4	1.384 (5)	C14—H14A	0.9300
C3—C4ⁱ	1.373 (5)	C15—C16	1.361 (6)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C3ⁱ	1.373 (5)	C16—C17	1.379 (5)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.431 (5)	C17—H17A	0.9300
C5—H5A	0.9300

O2—Cu1—N2	93.38 (11)	O2—C7—C6	125.0 (3)
O2—Cu1—O1	171.34 (11)	C8—C7—C6	117.5 (3)
N2—Cu1—O1	81.23 (11)	O3—C8—C9	124.6 (4)
O2—Cu1—N3	90.95 (11)	O3—C8—C7	114.2 (3)
N2—Cu1—N3	175.52 (12)	C9—C8—C7	121.2 (3)
O1—Cu1—N3	94.59 (11)	C8—C9—C10	120.2 (4)
C1—N1—N2	108.1 (3)	C8—C9—H9A	119.9
C5—N2—N1	117.7 (3)	C10—C9—H9A	119.9
C5—N2—Cu1	127.1 (3)	C11—C10—C9	120.3 (4)
N1—N2—Cu1	115.2 (2)	C11—C10—H10A	119.9
C13—N3—C17	117.4 (3)	C9—C10—H10A	119.9
C13—N3—Cu1	121.4 (2)	C10—C11—C6	121.1 (4)
C17—N3—Cu1	121.2 (3)	C10—C11—H11A	119.4
C1—O1—Cu1	110.1 (2)	C6—C11—H11A	119.4
C7—O2—Cu1	127.4 (2)	O3—C12—H12A	109.5
C8—O3—C12	116.7 (3)	O3—C12—H12B	109.5
O1—C1—N1	125.3 (3)	H12A—C12—H12B	109.5
O1—C1—C2	117.4 (3)	O3—C12—H12C	109.5
N1—C1—C2	117.3 (3)	H12A—C12—H12C	109.5
C3—C2—C4	117.3 (3)	H12B—C12—H12C	109.5
C3—C2—C1	122.4 (3)	N3—C13—C14	122.6 (4)
C4—C2—C1	120.2 (3)	N3—C13—H13A	118.7
C4ⁱ—C3—C2	121.4 (4)	C14—C13—H13A	118.7
C4ⁱ—C3—H3A	119.3	C13—C14—C15	119.5 (4)
C2—C3—H3A	119.3	C13—C14—H14A	120.2
C3ⁱ—C4—C2	121.3 (3)	C15—C14—H14A	120.2
C3ⁱ—C4—H4A	119.4	C16—C15—C14	118.4 (4)
C2—C4—H4A	119.4	C16—C15—H15A	120.8
N2—C5—C6	125.1 (3)	C14—C15—H15A	120.8
N2—C5—H5A	117.5	C15—C16—C17	119.6 (4)
C6—C5—H5A	117.5	C15—C16—H16A	120.2
C11—C6—C7	119.6 (4)	C17—C16—H16A	120.2
C11—C6—C5	118.4 (3)	N3—C17—C16	122.4 (4)
C7—C6—C5	121.9 (3)	N3—C17—H17A	118.8
O2—C7—C8	117.5 (3)	C16—C17—H17A	118.8

C1—N1—N2—C5	176.5 (3)	N2—C5—C6—C11	−177.6 (4)
C1—N1—N2—Cu1	−2.8 (4)	N2—C5—C6—C7	3.2 (6)
O2—Cu1—N2—C5	−3.7 (3)	Cu1—O2—C7—C8	176.9 (3)
O1—Cu1—N2—C5	−176.9 (3)	Cu1—O2—C7—C6	−2.6 (5)
O2—Cu1—N2—N1	175.5 (2)	C11—C6—C7—O2	178.7 (4)
O1—Cu1—N2—N1	2.4 (2)	C5—C6—C7—O2	−2.2 (6)
O2—Cu1—N3—C13	−179.7 (3)	C11—C6—C7—C8	−0.8 (5)
O1—Cu1—N3—C13	−6.4 (3)	C5—C6—C7—C8	178.4 (3)
O2—Cu1—N3—C17	−0.3 (3)	C12—O3—C8—C9	−4.8 (6)
O1—Cu1—N3—C17	173.0 (3)	C12—O3—C8—C7	174.2 (3)
N2—Cu1—O1—C1	−1.4 (2)	O2—C7—C8—O3	1.7 (5)
N3—Cu1—O1—C1	177.0 (2)	C6—C7—C8—O3	−178.8 (3)
N2—Cu1—O2—C7	4.7 (3)	O2—C7—C8—C9	−179.2 (4)
N3—Cu1—O2—C7	−174.2 (3)	C6—C7—C8—C9	0.3 (6)
Cu1—O1—C1—N1	0.1 (5)	O3—C8—C9—C10	179.8 (4)
Cu1—O1—C1—C2	178.6 (2)	C7—C8—C9—C10	0.8 (6)
N2—N1—C1—O1	1.8 (5)	C8—C9—C10—C11	−1.4 (6)
N2—N1—C1—C2	−176.8 (3)	C9—C10—C11—C6	0.9 (6)
O1—C1—C2—C3	176.4 (4)	C7—C6—C11—C10	0.2 (6)
N1—C1—C2—C3	−4.9 (6)	C5—C6—C11—C10	−179.0 (4)
O1—C1—C2—C4	−4.3 (5)	C17—N3—C13—C14	0.0 (6)
N1—C1—C2—C4	174.3 (4)	Cu1—N3—C13—C14	179.5 (3)
C4—C2—C3—C4ⁱ	−0.2 (8)	N3—C13—C14—C15	0.1 (6)
C1—C2—C3—C4ⁱ	179.1 (4)	C13—C14—C15—C16	0.4 (6)
C3—C2—C4—C3ⁱ	0.2 (8)	C14—C15—C16—C17	−0.9 (6)
C1—C2—C4—C3ⁱ	−179.1 (4)	C13—N3—C17—C16	−0.6 (6)
N1—N2—C5—C6	−178.7 (3)	Cu1—N3—C17—C16	180.0 (3)
Cu1—N2—C5—C6	0.6 (6)	C15—C16—C17—N3	1.0 (6)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₂₄H₁₈N₄O₆)(C₅H₅N)₂]
M_r	743.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	153
a, b, c (Å)	4.8474 (2), 15.2776 (6), 20.5546 (6)
β (°)	96.113 (4)
V (Å³)	1513.55 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.45 × 0.32 × 0.22

Data collection
Diffractometer	Agilent Gemini S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.447, 0.615
No. of measured, independent and observed [I > 2σ(I)] reflections	5837, 2658, 2113
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.06
No. of reflections	2658
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.35

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Acknowledgements

This project was supported financially by the Natural Science Foundation of Fujian Province of China (No. D1310010).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Banerjee, S., Mondal, S., Sen, S., Das, S., Hughes, D. L., Rizzoli, C., Desplanches, C., Mandal, C. & Mitra, S. (2009). Dalton Trans. 34, 6849–6860. Web of Science CSD CrossRef PubMed Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
He, Z., He, C., Wang, Z.-M., Gao, E.-Q., Liu, Y. & Yan, C.-H. (2004). Dalton Trans. pp. 502–504. Web of Science CSD CrossRef Google Scholar
Lin, P. H., Korobkov, I., Burchell, T. J. & Murugesu, M. (2012). Dalton Trans. 41, 13649–13655. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mistri, S., Zangrando, E. & Manna, S. C. (2013). Polyhedron, 49, 252–258. Web of Science CSD CrossRef CAS Google Scholar
Qiao, Y., Yin, H. & Cui, J. (2007). Acta Cryst. E63, o4819. 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
Shulgin, E. F., Trush, Y. V., Konnik, O. V., Rusanov, E. B., Zub, V. Y. & Minin, V. V. (2011). Zh. Neorg. Khim. 56, 755–756. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, H.-D., Cui, J.-C. & Qiao, Y.-L. (2008). Polyhedron, 27, 2157–2166. Web of Science CSD CrossRef CAS Google Scholar
Zhu, X., He, C., Dong, D.-P., Liu, Y. & Duan, C.-Y. (2010). Dalton Trans. 39, 10051–10055. Web of Science CSD CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.