[μ2-N (2),N (2')-Bis(3-meth-oxy-2-oxido-benzyl-idene)benzene-1,3-dicarbo-hydrazi-dato]bis-[pyridine-copper(II)].

In the centrosymmetric dinuclear title complex, [Cu2(C24H18N4O6)(C5H5N)2], the Cu(II) ions is tetra-coordinated by two O-atoms and one N-donor of the bridging terephthalo-hydra-zonate 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.

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 = 743.70

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.06

2658 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) I, a. DOI: 10.1107/S1600536813030286/fj2648sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu2(C24H18N4O6)(C5H5N)2]	F(000) = 760
Mr = 743.70	Dx = 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

Agilent Gemini S Ultra diffractometer	2658 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2113 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 15.9149 pixels mm-1	θmax = 66.5°, θmin = 3.6°
ω scans	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→17
Tmin = 0.447, Tmax = 0.615	l = −24→24
5837 measured reflections

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(Fo2) + (0.0637P)2 + 0.5957P] where P = (Fo2 + 2Fc2)/3
2658 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)