Bis[μ-4-hydr­oxy-N′-(4-meth­oxy-2-oxido­benzyl­idene)benzohydrazidato]bis­[pyridine­copper(II)]

Mohd Lair, N.; Khaledi, H.; Mohd Ali, H.; Puteh, R.

doi:10.1107/S1600536810011323

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m470

doi:10.1107/S1600536810011323

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Bis[μ-4-hydroxy-N′-(4-methoxy-2-oxidobenzylidene)benzohydrazidato]bis[pyridinecopper(II)]

Nooraziah Mohd Lair,^a Hamid Khaledi,^a ^* Hapipah Mohd Ali ^a and Rustam Puteh ^b

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Physics, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@perdana.um.edu.my

(Received 8 March 2010; accepted 25 March 2010; online 31 March 2010)

In the title compound, [Cu₂(C₁₅H₁₂N₂O₄)₂(C₆H₅N)₂], each Cu^II atom is chelated by the tridentate doubly deprotonated Schiff base and a pyridine molecule 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 interactions 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_r = 853.83
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 1.01
4035 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.26 e Å⁻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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound is the pyridine adduct of the copper complex of 4-hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide. In the asymmetric unit, which contains one half of the formula unit, the copper ion is four coordinated in an approximately planar environment, the highest deviation from the best plane passing through all non-H atoms being 0.348 (2) Å for O2. From this point of view, it is similar to the structure of the 4-nitrated analogous compound (Mohd Lair et al. 2009b). However, replacement of the electron-withdrawing nitro group by a hydroxy group resulted in bridging the copper ions by O2 atoms from the symmetry related Schiff bases at (-x+1, -y+2, -z), forming a centrosymmetric dinuclear Cu^II complex. The distance of Cu1—O2ⁱis 2.778 (1) Å which is similar to the length of the Cu—O bridge (2.783 Å) in the dinuclear copper (II) salphen complex (Yu et al. 2008). Morever, there is a weak interaction between the copper ions and O3 atoms from the symmetry related molecules at (-x+1, -y+1, -z) with Cu1—O3ⁱⁱⁱdistance of 3.576 (2) Å, which binds the molecules in one-dimensional infinite chains. Intermolecular hydrogen bonds between the hydroxy groups and the imine N atoms of the neighboring molecules connect the complexes to each other.

Related literature top

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 crystal structure of dinuclear copper(II) salphen complex with a similar coordination see: Yu et al. (2008).

Experimental top

The Schiff base ligand was prepared as reported previously (Mohd Lair et al., 2009a). A mixture of the Schiff base (0.57 g, 2 mmol) and copper(II) acetate monohydrate (0.4 g, 2 mmol) in the presence of a few drops of triethylamine was refluxed in ethanol (100 ml) for 5 hours. The resulting green precipitate was then filtered, washed with ethanol and dried over silica gel. The green crystal of the title compound was obtained by slow evaporation of a pyridine solution of the compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at 60% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A view of the interaction between Cu1 and O3 from the symmetry related molecule at (-x+1, -y+1, -z). Hydrogen atoms have been omitted for clarity.

Bis[µ-4-hydroxy-N'-(4-methoxy-2- oxidobenzylidene)benzohydrazidato]bis[pyridinecopper(II)] top

Crystal data top

[Cu₂(C₁₅H₁₂N₂O₄)₂(C₆H₅N)₂]	F(000) = 876
M_r = 853.83	D_x = 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

Data collection top

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

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)] = 0.030	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(F_o²) + (0.0332P)² + 1.6174P] where P = (F_o² + 2F_c²)/3
4035 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Cu₂(C₁₅H₁₂N₂O₄)₂(C₆H₅N)₂]	V = 1768.70 (7) Å³
M_r = 853.83	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.3666 (3) Å	µ = 1.27 mm⁻¹
b = 7.9402 (2) Å	T = 100 K
c = 16.7229 (3) Å	0.26 × 0.12 × 0.01 mm
β = 94.775 (1)°

Data collection top

Bruker SMART APEXII diffractometer	4035 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3473 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.991	R_int = 0.021
10121 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.41 e Å⁻³
4035 reflections	Δρ_min = −0.26 e Å⁻³
257 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₅H₁₂N₂O₄)₂(C₆H₅N)₂]
M_r	853.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.3666 (3), 7.9402 (2), 16.7229 (3)
β (°)	94.775 (1)
V (Å³)	1768.70 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.26 × 0.12 × 0.01

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.734, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10121, 4035, 3473
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.01
No. of reflections	4035
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.830 (10)	1.914 (10)	2.743 (2)	178 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, o189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009b). Acta Cryst. E65, m121. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
Yu, G., Ding, Y., Wang, L., Fu, Z. & Hu, X. (2008). Acta Cryst. E64, m504. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page m470

doi:10.1107/S1600536810011323

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[μ-4-hydr­­oxy-N′-(4-meth­­oxy-2-oxido­benzyl­­idene)benzohydrazidato]bis­­[pyridine­copper(II)]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[μ-4-hydroxy-N′-(4-methoxy-2-oxidobenzylidene)benzohydrazidato]bis[pyridinecopper(II)]