Bis[μ-4-hydr-oxy-N'-(4-meth-oxy-2-oxido-benzyl-idene)benzohydrazidato]bis-[pyridine-copper(II)].

In the title compound, [Cu(2)(C(15)H(12)N(2)O(4))(2)(C(6)H(5)N)(2)], each Cu(II) atom is chelated by the tridentate doubly deprotonated Schiff base and a pyridine mol-ecule in a nearly planar environment (r.m.s. deviation for all non-H atoms = 0.107 Å). The metal ions are bridged by one O atom from the symmetry-related Schiff base ligands, forming a centrosymmetric dinuclear copper(II) complex. The dimeric complex is linked to another dimer via weaker Cu-O inter-actions and also O-H⋯N hydrogen bonds.

Related literature

For the crystal structure of the monohydrated Schiff base ligand, see: Mohd Lair et al. (2009a ▶). For the structure of the pyridine adduct of the copper complex of the 4-nitro analog, see: Mohd Lair et al. (2009b ▶). For the crystal structure of a dinuclear copper(II) salphen complex with a similar coordin­ation, see: Yu et al. (2008 ▶).

Experimental

Crystal data

[Cu2(C15H12N2O4)2(C6H5N)2]

M = 853.83

Monoclinic,

a = 13.3666 (3) Å

b = 7.9402 (2) Å

c = 16.7229 (3) Å

β = 94.775 (1)°

V = 1768.70 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.27 mm−1

T = 100 K

0.26 × 0.12 × 0.01 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.734, T max = 0.991

10121 measured reflections

4035 independent reflections

3473 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.075

S = 1.01

4035 reflections

257 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011323/om2326sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011323/om2326Isup2.hkl

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

[Cu2(C15H12N2O4)2(C6H5N)2]	F(000) = 876
Mr = 853.83	Dx = 1.603 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4307 reflections
a = 13.3666 (3) Å	θ = 2.8–30.2°
b = 7.9402 (2) Å	µ = 1.27 mm−1
c = 16.7229 (3) Å	T = 100 K
β = 94.775 (1)°	Lath, pale green
V = 1768.70 (7) Å3	0.26 × 0.12 × 0.01 mm
Z = 2

Bruker SMART APEXII diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	3473 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.734, Tmax = 0.991	k = −7→10
10121 measured reflections	l = −21→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0332P)2 + 1.6174P] where P = (Fo2 + 2Fc2)/3
4035 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.511594 (16)	0.77247 (3)	−0.003528 (13)	0.01666 (8)
O1	0.36136 (10)	1.26026 (19)	0.39906 (8)	0.0223 (3)
H1	0.3017 (9)	1.277 (3)	0.4068 (15)	0.033*
O2	0.49690 (10)	0.92300 (18)	0.08564 (8)	0.0189 (3)
O3	0.51275 (10)	0.62681 (19)	−0.09181 (8)	0.0231 (3)
O4	0.39119 (10)	0.28970 (18)	−0.31267 (8)	0.0226 (3)
N1	0.33448 (12)	0.8237 (2)	0.07305 (9)	0.0165 (3)
N2	0.37010 (11)	0.74438 (19)	0.00604 (9)	0.0159 (3)
N3	0.66146 (12)	0.7893 (2)	0.00376 (9)	0.0169 (3)
C1	0.36838 (14)	1.1762 (2)	0.32891 (11)	0.0178 (4)
C2	0.28481 (14)	1.1087 (2)	0.28451 (11)	0.0191 (4)
H2	0.2200	1.1206	0.3032	0.023*
C3	0.29600 (14)	1.0246 (2)	0.21334 (11)	0.0178 (4)
H3	0.2385	0.9800	0.1834	0.021*
C4	0.39081 (14)	1.0044 (2)	0.18485 (11)	0.0166 (4)
C5	0.47366 (14)	1.0747 (3)	0.22963 (11)	0.0207 (4)
H5	0.5385	1.0642	0.2108	0.025*
C6	0.46282 (14)	1.1589 (3)	0.30079 (11)	0.0213 (4)
H6	0.5200	1.2051	0.3305	0.026*
C7	0.40775 (14)	0.9119 (2)	0.11040 (10)	0.0165 (4)
C8	0.30712 (14)	0.6628 (2)	−0.04221 (11)	0.0171 (4)
H8	0.2384	0.6637	−0.0316	0.021*
C9	0.33470 (14)	0.5707 (2)	−0.11095 (11)	0.0168 (4)
C10	0.25867 (14)	0.4850 (2)	−0.15879 (11)	0.0192 (4)
H10	0.1914	0.4927	−0.1448	0.023*
C11	0.27833 (14)	0.3915 (3)	−0.22433 (11)	0.0206 (4)
H11	0.2258	0.3346	−0.2552	0.025*
C12	0.37823 (14)	0.3815 (2)	−0.24505 (11)	0.0188 (4)
C13	0.45461 (14)	0.4615 (3)	−0.20009 (11)	0.0197 (4)
H13	0.5214	0.4524	−0.2151	0.024*
C14	0.43541 (14)	0.5572 (2)	−0.13177 (11)	0.0182 (4)
C15	0.48858 (15)	0.2908 (3)	−0.34204 (12)	0.0251 (4)
H15A	0.5092	0.4073	−0.3509	0.038*
H15B	0.4865	0.2286	−0.3928	0.038*
H15C	0.5368	0.2373	−0.3026	0.038*
C16	0.71550 (15)	0.7054 (3)	−0.04781 (11)	0.0201 (4)
H16	0.6810	0.6402	−0.0890	0.024*
C17	0.81867 (15)	0.7103 (3)	−0.04325 (12)	0.0239 (4)
H17	0.8543	0.6481	−0.0803	0.029*
C18	0.87010 (15)	0.8063 (3)	0.01561 (12)	0.0249 (4)
H18	0.9413	0.8124	0.0196	0.030*
C19	0.81467 (15)	0.8934 (3)	0.06856 (12)	0.0249 (4)
H19	0.8475	0.9612	0.1095	0.030*
C20	0.71148 (15)	0.8808 (3)	0.06130 (11)	0.0207 (4)
H20	0.6744	0.9394	0.0986	0.025*

	U11	U22	U33	U12	U13	U23
Cu1	0.01512 (12)	0.01935 (13)	0.01608 (12)	0.00010 (9)	0.00468 (8)	−0.00223 (9)
O1	0.0198 (7)	0.0291 (8)	0.0184 (7)	0.0027 (6)	0.0046 (5)	−0.0057 (6)
O2	0.0171 (6)	0.0236 (7)	0.0171 (6)	−0.0008 (6)	0.0066 (5)	−0.0034 (6)
O3	0.0162 (6)	0.0304 (8)	0.0231 (7)	−0.0017 (6)	0.0048 (5)	−0.0092 (6)
O4	0.0235 (7)	0.0255 (8)	0.0196 (7)	−0.0019 (6)	0.0061 (5)	−0.0054 (6)
N1	0.0192 (7)	0.0173 (8)	0.0139 (7)	0.0010 (6)	0.0069 (6)	0.0004 (6)
N2	0.0175 (7)	0.0155 (8)	0.0154 (7)	0.0010 (6)	0.0063 (6)	0.0004 (6)
N3	0.0175 (7)	0.0172 (8)	0.0162 (7)	0.0013 (6)	0.0031 (6)	0.0023 (6)
C1	0.0223 (9)	0.0170 (9)	0.0147 (8)	0.0032 (7)	0.0045 (7)	0.0009 (7)
C2	0.0159 (9)	0.0220 (10)	0.0204 (9)	0.0018 (7)	0.0068 (7)	−0.0001 (8)
C3	0.0176 (9)	0.0166 (10)	0.0195 (9)	−0.0011 (7)	0.0029 (7)	−0.0005 (7)
C4	0.0194 (9)	0.0156 (9)	0.0154 (8)	0.0015 (7)	0.0041 (7)	0.0024 (7)
C5	0.0169 (9)	0.0262 (11)	0.0196 (9)	0.0003 (8)	0.0051 (7)	0.0005 (8)
C6	0.0175 (9)	0.0262 (11)	0.0202 (9)	−0.0003 (8)	0.0015 (7)	−0.0016 (8)
C7	0.0196 (9)	0.0158 (10)	0.0147 (8)	0.0019 (7)	0.0055 (7)	0.0043 (7)
C8	0.0176 (9)	0.0153 (9)	0.0192 (9)	−0.0003 (7)	0.0064 (7)	0.0034 (7)
C9	0.0201 (9)	0.0141 (9)	0.0165 (8)	−0.0002 (7)	0.0038 (7)	0.0018 (7)
C10	0.0167 (9)	0.0196 (10)	0.0219 (9)	−0.0007 (7)	0.0059 (7)	0.0022 (8)
C11	0.0202 (9)	0.0212 (10)	0.0202 (9)	−0.0032 (8)	0.0015 (7)	−0.0002 (8)
C12	0.0248 (10)	0.0155 (9)	0.0166 (9)	0.0006 (7)	0.0054 (7)	0.0010 (7)
C13	0.0169 (9)	0.0217 (10)	0.0213 (9)	0.0006 (7)	0.0058 (7)	−0.0014 (8)
C14	0.0204 (9)	0.0164 (9)	0.0182 (9)	0.0001 (7)	0.0042 (7)	0.0013 (7)
C15	0.0250 (10)	0.0289 (11)	0.0224 (10)	0.0032 (9)	0.0084 (8)	−0.0036 (9)
C16	0.0221 (9)	0.0211 (10)	0.0176 (9)	−0.0010 (8)	0.0048 (7)	−0.0016 (8)
C17	0.0206 (9)	0.0296 (11)	0.0225 (9)	0.0012 (8)	0.0074 (8)	−0.0028 (8)
C18	0.0184 (9)	0.0343 (12)	0.0221 (9)	−0.0018 (9)	0.0027 (7)	0.0000 (9)
C19	0.0231 (10)	0.0305 (12)	0.0209 (9)	−0.0016 (9)	0.0006 (8)	−0.0048 (8)
C20	0.0222 (9)	0.0219 (10)	0.0184 (9)	0.0018 (8)	0.0043 (7)	−0.0005 (8)

Cu1—O3	1.8765 (14)	C5—H5	0.9500
Cu1—N2	1.9242 (15)	C6—H6	0.9500
Cu1—O2	1.9338 (13)	C8—C9	1.436 (3)
Cu1—N3	2.0012 (16)	C8—H8	0.9500
Cu1—O2i	2.7784 (14)	C9—C10	1.414 (3)
O1—C1	1.360 (2)	C9—C14	1.422 (3)
O1—H1	0.830 (10)	C10—C11	1.367 (3)
O2—C7	1.297 (2)	C10—H10	0.9500
O3—C14	1.306 (2)	C11—C12	1.409 (3)
O4—C12	1.368 (2)	C11—H11	0.9500
O4—C15	1.429 (2)	C12—C13	1.372 (3)
N1—C7	1.318 (2)	C13—C14	1.413 (3)
N1—N2	1.403 (2)	C13—H13	0.9500
N2—C8	1.291 (2)	C15—H15A	0.9800
N3—C20	1.340 (2)	C15—H15B	0.9800
N3—C16	1.346 (2)	C15—H15C	0.9800
C1—C6	1.390 (3)	C16—C17	1.375 (3)
C1—C2	1.396 (3)	C16—H16	0.9500
C2—C3	1.384 (3)	C17—C18	1.382 (3)
C2—H2	0.9500	C17—H17	0.9500
C3—C4	1.400 (3)	C18—C19	1.386 (3)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.400 (3)	C19—C20	1.378 (3)
C4—C7	1.479 (2)	C19—H19	0.9500
C5—C6	1.383 (3)	C20—H20	0.9500
O3—Cu1—N2	93.82 (6)	N2—C8—C9	123.94 (17)
O3—Cu1—O2	174.65 (6)	N2—C8—H8	118.0
N2—Cu1—O2	81.02 (6)	C9—C8—H8	118.0
O3—Cu1—N3	90.87 (6)	C10—C9—C14	118.39 (17)
N2—Cu1—N3	171.29 (6)	C10—C9—C8	118.51 (16)
O2—Cu1—N3	94.43 (6)	C14—C9—C8	123.06 (17)
O3—Cu1—O2i	98.64 (5)	C11—C10—C9	122.52 (17)
N2—Cu1—O2i	98.16 (5)	C11—C10—H10	118.7
O2—Cu1—O2i	80.83 (5)	C9—C10—H10	118.7
N3—Cu1—O2i	88.37 (5)	C10—C11—C12	118.48 (18)
C1—O1—H1	110.6 (18)	C10—C11—H11	120.8
C7—O2—Cu1	111.04 (12)	C12—C11—H11	120.8
C14—O3—Cu1	127.26 (12)	O4—C12—C13	124.03 (17)
C12—O4—C15	117.55 (15)	O4—C12—C11	114.89 (17)
C7—N1—N2	109.19 (14)	C13—C12—C11	121.07 (17)
C8—N2—N1	118.52 (15)	C12—C13—C14	120.99 (17)
C8—N2—Cu1	126.91 (13)	C12—C13—H13	119.5
N1—N2—Cu1	114.57 (11)	C14—C13—H13	119.5
C20—N3—C16	117.79 (17)	O3—C14—C13	116.87 (16)
C20—N3—Cu1	121.15 (13)	O3—C14—C9	124.60 (17)
C16—N3—Cu1	121.04 (13)	C13—C14—C9	118.53 (17)
O1—C1—C6	118.04 (17)	O4—C15—H15A	109.5
O1—C1—C2	122.52 (16)	O4—C15—H15B	109.5
C6—C1—C2	119.43 (17)	H15A—C15—H15B	109.5
C3—C2—C1	120.25 (17)	O4—C15—H15C	109.5
C3—C2—H2	119.9	H15A—C15—H15C	109.5
C1—C2—H2	119.9	H15B—C15—H15C	109.5
C2—C3—C4	120.92 (17)	N3—C16—C17	122.65 (18)
C2—C3—H3	119.5	N3—C16—H16	118.7
C4—C3—H3	119.5	C17—C16—H16	118.7
C3—C4—C5	118.07 (17)	C16—C17—C18	119.48 (18)
C3—C4—C7	123.35 (17)	C16—C17—H17	120.3
C5—C4—C7	118.58 (16)	C18—C17—H17	120.3
C6—C5—C4	121.20 (17)	C17—C18—C19	118.02 (19)
C6—C5—H5	119.4	C17—C18—H18	121.0
C4—C5—H5	119.4	C19—C18—H18	121.0
C5—C6—C1	120.12 (18)	C20—C19—C18	119.46 (19)
C5—C6—H6	119.9	C20—C19—H19	120.3
C1—C6—H6	119.9	C18—C19—H19	120.3
O2—C7—N1	123.45 (16)	N3—C20—C19	122.60 (18)
O2—C7—C4	116.35 (16)	N3—C20—H20	118.7
N1—C7—C4	120.20 (16)	C19—C20—H20	118.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ii	0.83 (1)	1.91 (1)	2.743 (2)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.83 (1)	1.91 (1)	2.743 (2)	178 (3)

Symmetry code: (i) .