cyclo-Tetra­kis[μ-N-(2-hydroxy­benzo­yl)-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)hydrazine(2–)]tetra­zinc(II) N,N-dimethyl­formamide tetra­solvate

Gao, Y.-X.; Wang, L.-B.; Niu, Y.-L.

doi:10.1107/S1600536807034514

Retracted: cyclo-Tetrakis[μ-N-(2-hydroxybenzoyl)-N′-(2-hydroxy-3-methoxybenzylidene)hydrazine(2–)]tetrazinc(II) N,N-dimethylformamide tetrasolvate

The title compound, [Zn₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO, is isostructural with its Co^II analogue. The compound contains N-(2-hydroxybenzoyl)-N-(2-hydroxy-3-methoxybenzylidene)hydrazine anions and Zn^II cations linked into tetrameric complexes about a position of $\overline{4}$ point symmetry. Each Zn^II cation is pentacoordinated with a distorted square-based pyramidal geometry. The ligand exhibits an intramolecular O—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034514/bi2214sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034514/bi2214Isup2.hkl Contains datablock I

CCDC reference: 1270865

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R factor = 0.046
wR factor = 0.154
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C16
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       2.20

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The title compound, [Zn₄(C₁₅H₁₂N₂O₄)₄].4C₃H₇NO, is isostructural with its Co^II analogue (Gao et al., 2007). As shown in Figure 1, each Zn^II cation is penta-coordinated by four O atoms and one N atom, forming a distorted square-based pyramidal geometry. The Zn—O bond lengths are in the range 1.936 (3)–2.275 Å, and Zn—N = 1.961 (4) Å. The Zn^II cations are linked into tetrameric complexes about positions of 4 point symmetry by four N-(2-hydroxybenzoyl)-N-(2-hydroxy-3-methoxybenzylidene)-hydrazine anions (Figure 2). The ligand exhibits an intramolecular O—H···N hydrogen bond.

Related literature top

One motivation to study hydrazine and its analogues is to understand better the mechanism of enzymes containing vitamin B6. For related literature, see: Maghler et al. (1982); Rath et al. (1997, 1998). For the analogous Co^II complex, see: Gao et al. (2007).

Experimental top

All chemicals were used as purchased from Shanghai chemical Co. Ltd. A mixture of zinc(II) acetate (0.5 mmol) and N-(2-hydroxybenzoyl)-N-(2-hydroxy-3-methoxybenzylidene)-hydrazine (0.5 mmol) in DMF (30 ml) was refluxed for 1 h then filtered. Colourless crystals were obtained after a few days standing at room temperature with a yield of 15%. Elemental analysis calculated: C 51.09, H 4.49, N 9.93%; found: C 51.01, H 4.55, N 9.90%.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing displacement ellipsoids at 50% probability for non-H atoms. Atoms labeled with the subscript I are generated by the symmetry operator -y + 3/4, x - 1/4, -z + 3/4.
	Fig. 2. Tetrameric complex formed about the position of 4 point symmetry.

cyclo-Tetrakis[µ-N-(2-hydroxybenzoyl)-N'-(2-hydroxy-3-µethoxybenzylidene)hydrazine(2-)]tetrazinc(II)} N,N-dimethylformamide tetrasolvate top

Crystal data top

[Zn₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO	D_x = 1.474 Mg m⁻³
M_r = 1690.93	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3529 reflections
Hall symbol: -I 4ad	θ = 1.7–25.5°
a = 24.1202 (10) Å	µ = 1.32 mm⁻¹
c = 13.093 (2) Å	T = 293 K
V = 7617.2 (12) Å³	Cube, colourless
Z = 4	0.15 × 0.15 × 0.15 mm
F(000) = 3488

Data collection top

Bruker APEXII CCD diffractometer	3529 independent reflections
Radiation source: fine-focus sealed tube	2249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
φ and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −29→26
T_min = 0.826, T_max = 0.826	k = −26→29
19270 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.076P)² + 20.3206P] where P = (F_o² + 2F_c²)/3
3529 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Zn₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO	Z = 4
M_r = 1690.93	Mo Kα radiation
Tetragonal, I4₁/a	µ = 1.32 mm⁻¹
a = 24.1202 (10) Å	T = 293 K
c = 13.093 (2) Å	0.15 × 0.15 × 0.15 mm
V = 7617.2 (12) Å³

Data collection top

Bruker APEXII CCD diffractometer	3529 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2249 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.826	R_int = 0.052
19270 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.154	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.076P)² + 20.3206P] where P = (F_o² + 2F_c²)/3
3529 reflections	Δρ_max = 0.43 e Å⁻³
248 parameters	Δρ_min = −0.30 e Å⁻³

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
C1	0.3405 (2)	0.2402 (2)	0.6596 (4)	0.0602 (14)
H1	0.3377	0.2495	0.7284	0.072*
C2	0.3006 (2)	0.2089 (2)	0.6154 (4)	0.0642 (15)
H2	0.2703	0.1975	0.6538	0.077*
C3	0.3046 (2)	0.1934 (2)	0.5123 (4)	0.0579 (13)
H3	0.2767	0.1718	0.4833	0.069*
C4	0.34886 (19)	0.20960 (19)	0.4540 (3)	0.0460 (11)
C5	0.3122 (3)	0.1772 (4)	0.2909 (5)	0.116 (3)
H5A	0.2997	0.1411	0.3118	0.175*
H5B	0.3233	0.1759	0.2205	0.175*
H5C	0.2827	0.2035	0.2989	0.175*
C6	0.39010 (18)	0.24382 (18)	0.4953 (3)	0.0410 (10)
C7	0.38608 (19)	0.25887 (19)	0.6020 (3)	0.0449 (11)
C8	0.42652 (19)	0.29078 (19)	0.6552 (3)	0.0473 (11)
H8	0.4225	0.2952	0.7253	0.057*
C9	0.54307 (19)	0.36577 (18)	0.6185 (4)	0.0451 (11)
C10	0.5861 (2)	0.39546 (19)	0.6751 (4)	0.0496 (12)
C11	0.6263 (2)	0.4233 (2)	0.6198 (5)	0.0648 (15)
H11	0.6246	0.4240	0.5489	0.078*
C12	0.6693 (3)	0.4505 (3)	0.6705 (7)	0.089 (2)
H12	0.6964	0.4696	0.6341	0.107*
C13	0.6710 (3)	0.4484 (3)	0.7795 (7)	0.096 (2)
H13	0.7002	0.4656	0.8134	0.115*
C14	0.6319 (3)	0.4226 (3)	0.8351 (6)	0.088 (2)
H14	0.6339	0.4225	0.9060	0.105*
C15	0.5884 (2)	0.3959 (2)	0.7857 (4)	0.0642 (15)
C16	0.2793 (4)	0.3665 (4)	0.6165 (8)	0.108 (3)
H16	0.2618	0.3529	0.6746	0.129*
C17	0.2830 (5)	0.3663 (6)	0.4320 (9)	0.205 (6)
H17A	0.2659	0.3988	0.4038	0.307*
H17B	0.2782	0.3358	0.3857	0.307*
H17C	0.3218	0.3730	0.4421	0.307*
C18	0.2097 (4)	0.3197 (4)	0.5211 (8)	0.134 (3)
H18A	0.1976	0.3105	0.5888	0.201*
H18B	0.2182	0.2863	0.4843	0.201*
H18C	0.1809	0.3396	0.4862	0.201*
N1	0.46812 (16)	0.31377 (15)	0.6114 (3)	0.0445 (9)
N2	0.50458 (16)	0.34242 (17)	0.6749 (3)	0.0494 (10)
N3	0.2579 (3)	0.3533 (3)	0.5269 (6)	0.114 (2)
O1	0.3203 (3)	0.3951 (3)	0.6286 (6)	0.157 (3)
O2	0.43283 (12)	0.25892 (13)	0.4338 (2)	0.0425 (7)
O3	0.54506 (13)	0.36375 (13)	0.5177 (2)	0.0488 (8)
O4	0.5508 (2)	0.3710 (2)	0.8454 (3)	0.0883 (13)
H4	0.5281	0.3546	0.8097	0.133*
O5	0.35790 (13)	0.19336 (14)	0.3519 (2)	0.0552 (9)
Zn1	0.48656 (2)	0.31666 (2)	0.46560 (4)	0.0434 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.064 (3)	0.079 (4)	0.037 (3)	−0.005 (3)	0.016 (2)	−0.003 (3)
C2	0.056 (3)	0.079 (4)	0.057 (3)	−0.016 (3)	0.016 (3)	0.001 (3)
C3	0.053 (3)	0.067 (3)	0.054 (3)	−0.012 (2)	0.004 (2)	−0.003 (3)
C4	0.051 (3)	0.052 (3)	0.034 (3)	−0.001 (2)	0.001 (2)	0.000 (2)
C5	0.094 (5)	0.182 (8)	0.073 (5)	−0.058 (5)	0.002 (4)	−0.053 (5)
C6	0.046 (3)	0.046 (3)	0.031 (2)	0.000 (2)	0.0032 (19)	0.0023 (19)
C7	0.050 (3)	0.053 (3)	0.031 (2)	−0.003 (2)	0.007 (2)	−0.001 (2)
C8	0.058 (3)	0.060 (3)	0.024 (2)	−0.003 (2)	0.011 (2)	−0.006 (2)
C9	0.053 (3)	0.046 (3)	0.036 (3)	0.006 (2)	−0.002 (2)	−0.010 (2)
C10	0.053 (3)	0.045 (3)	0.051 (3)	0.007 (2)	−0.004 (2)	−0.014 (2)
C11	0.057 (3)	0.059 (3)	0.079 (4)	0.000 (3)	−0.001 (3)	−0.019 (3)
C12	0.060 (4)	0.072 (4)	0.134 (7)	−0.009 (3)	0.004 (4)	−0.032 (4)
C13	0.077 (5)	0.078 (5)	0.132 (7)	0.001 (4)	−0.036 (5)	−0.039 (5)
C14	0.094 (5)	0.087 (5)	0.082 (5)	0.010 (4)	−0.039 (4)	−0.030 (4)
C15	0.072 (4)	0.067 (3)	0.054 (3)	0.009 (3)	−0.017 (3)	−0.017 (3)
C16	0.097 (6)	0.123 (7)	0.102 (7)	0.008 (5)	−0.005 (5)	0.013 (5)
C17	0.198 (12)	0.305 (18)	0.111 (9)	−0.080 (12)	−0.029 (9)	0.033 (10)
C18	0.114 (7)	0.129 (7)	0.159 (10)	0.003 (6)	−0.016 (6)	−0.014 (7)
N1	0.055 (2)	0.055 (2)	0.0239 (19)	−0.0004 (18)	0.0017 (17)	−0.0064 (17)
N2	0.055 (2)	0.065 (3)	0.028 (2)	−0.004 (2)	−0.0002 (18)	−0.0077 (18)
N3	0.098 (5)	0.161 (7)	0.085 (5)	−0.007 (5)	−0.018 (4)	0.011 (5)
O1	0.139 (6)	0.199 (7)	0.131 (6)	−0.023 (5)	−0.025 (5)	−0.010 (5)
O2	0.0501 (18)	0.0563 (18)	0.0211 (14)	−0.0046 (14)	0.0036 (13)	−0.0038 (13)
O3	0.061 (2)	0.0550 (19)	0.0307 (18)	−0.0062 (15)	0.0049 (15)	−0.0041 (14)
O4	0.114 (4)	0.114 (4)	0.037 (2)	−0.025 (3)	−0.015 (2)	−0.010 (2)
O5	0.056 (2)	0.072 (2)	0.0377 (19)	−0.0142 (16)	0.0000 (15)	−0.0126 (16)
Zn1	0.0547 (4)	0.0517 (4)	0.0238 (3)	−0.0025 (2)	0.0031 (2)	−0.0027 (2)

Geometric parameters (Å, º) top

C1—C2	1.352 (7)	C12—H12	0.930
C1—C7	1.408 (6)	C13—C14	1.343 (10)
C1—H1	0.930	C13—H13	0.930
C2—C3	1.404 (8)	C14—C15	1.390 (8)
C2—H2	0.930	C14—H14	0.930
C3—C4	1.370 (6)	C15—O4	1.342 (7)
C3—H3	0.930	C16—O1	1.214 (10)
C4—C6	1.401 (6)	C16—N3	1.321 (10)
C4—O5	1.411 (5)	C16—H16	0.930
C5—O5	1.416 (7)	C17—N3	1.418 (12)
C5—H5A	0.960	C17—H17A	0.960
C5—H5B	0.960	C17—H17B	0.960
C5—H5C	0.960	C17—H17C	0.960
C6—O2	1.358 (5)	C18—N3	1.418 (10)
C6—C7	1.446 (6)	C18—H18A	0.960
C7—C8	1.424 (6)	C18—H18B	0.960
C8—N1	1.282 (6)	C18—H18C	0.960
C8—H8	0.930	N1—N2	1.393 (5)
C9—N2	1.313 (6)	O2—Zn1ⁱ	2.028 (3)
C9—O3	1.322 (5)	O4—H4	0.820
C9—C10	1.463 (6)	O5—Zn1ⁱ	2.275 (3)
C10—C11	1.383 (7)	Zn1—N1	1.961 (4)
C10—C15	1.449 (7)	Zn1—O2	1.948 (3)
C11—C12	1.395 (8)	Zn1—O3	1.936 (3)
C11—H11	0.930	Zn1—O2ⁱⁱ	2.028 (3)
C12—C13	1.429 (11)	Zn1—O5ⁱⁱ	2.275 (3)

C2—C1—C7	120.3 (5)	C15—C14—H14	120.3
C2—C1—H1	119.9	O4—C15—C14	116.6 (6)
C7—C1—H1	119.9	O4—C15—C10	123.6 (5)
C1—C2—C3	120.8 (5)	C14—C15—C10	119.8 (6)
C1—C2—H2	119.6	O1—C16—N3	124.8 (9)
C3—C2—H2	119.6	O1—C16—H16	117.6
C4—C3—C2	120.8 (5)	N3—C16—H16	117.6
C4—C3—H3	119.6	N3—C17—H17A	109.4
C2—C3—H3	119.6	N3—C17—H17B	109.5
C3—C4—C6	120.5 (4)	H17A—C17—H17B	109.5
C3—C4—O5	124.7 (4)	N3—C17—H17C	109.5
C6—C4—O5	114.8 (4)	H17A—C17—H17C	109.5
O5—C5—H5A	109.5	H17B—C17—H17C	109.5
O5—C5—H5B	109.5	N3—C18—H18A	109.5
H5A—C5—H5B	109.5	N3—C18—H18B	109.5
O5—C5—H5C	109.5	H18A—C18—H18B	109.5
H5A—C5—H5C	109.5	N3—C18—H18C	109.5
H5B—C5—H5C	109.5	H18A—C18—H18C	109.5
O2—C6—C4	117.9 (4)	H18B—C18—H18C	109.5
O2—C6—C7	123.8 (4)	C8—N1—N2	116.3 (4)
C4—C6—C7	118.2 (4)	C8—N1—Zn1	128.9 (3)
C1—C7—C8	116.5 (4)	N2—N1—Zn1	114.8 (3)
C1—C7—C6	119.3 (4)	C9—N2—N1	108.9 (4)
C8—C7—C6	124.2 (4)	C16—N3—C17	123.9 (9)
N1—C8—C7	123.5 (4)	C16—N3—C18	120.4 (8)
N1—C8—H8	118.3	C17—N3—C18	115.4 (8)
C7—C8—H8	118.3	C6—O2—Zn1	124.7 (3)
N2—C9—O3	124.8 (4)	C6—O2—Zn1ⁱ	120.3 (3)
N2—C9—C10	115.3 (4)	Zn1—O2—Zn1ⁱ	113.10 (14)
O3—C9—C10	119.9 (4)	C9—O3—Zn1	110.3 (3)
C11—C10—C15	119.5 (5)	C15—O4—H4	109.5
C11—C10—C9	118.0 (5)	C4—O5—C5	119.4 (4)
C15—C10—C9	122.5 (5)	C4—O5—Zn1ⁱ	111.4 (3)
C10—C11—C12	120.0 (6)	C5—O5—Zn1ⁱ	122.0 (4)
C10—C11—H11	120.0	O3—Zn1—O2	168.57 (13)
C12—C11—H11	120.0	O3—Zn1—N1	80.97 (14)
C11—C12—C13	118.6 (7)	O2—Zn1—N1	91.83 (14)
C11—C12—H12	120.7	O3—Zn1—O2ⁱⁱ	98.19 (13)
C13—C12—H12	120.7	O2—Zn1—O2ⁱⁱ	88.56 (12)
C14—C13—C12	122.5 (6)	N1—Zn1—O2ⁱⁱ	177.14 (14)
C14—C13—H13	118.7	O3—Zn1—O5ⁱⁱ	90.08 (13)
C12—C13—H13	118.7	O2—Zn1—O5ⁱⁱ	100.61 (13)
C13—C14—C15	119.5 (7)	N1—Zn1—O5ⁱⁱ	107.61 (13)
C13—C14—H14	120.3	O2ⁱⁱ—Zn1—O5ⁱⁱ	75.09 (11)

Symmetry codes: (i) −y+3/4, x−1/4, −z+3/4; (ii) y+1/4, −x+3/4, −z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N2	0.82	1.88	2.589 (5)	144

Experimental details

Crystal data
Chemical formula	[Zn₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO
M_r	1690.93
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	24.1202 (10), 13.093 (2)
V (Å³)	7617.2 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.15 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.826, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	19270, 3529, 2249
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.154, 1.00
No. of reflections	3529
No. of parameters	248
H-atom treatment	H-atom parameters not refined
	w = 1/[σ²(F_o²) + (0.076P)² + 20.3206P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected bond lengths (Å) top

Zn1—N1	1.961 (4)	Zn1—O2ⁱ	2.028 (3)
Zn1—O2	1.948 (3)	Zn1—O5ⁱ	2.275 (3)
Zn1—O3	1.936 (3)

Symmetry code: (i) y+1/4, −x+3/4, −z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N2	0.82	1.88	2.589 (5)	144

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

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Retracted: cyclo-Tetra­kis[μ-N-(2-hydroxy­benzo­yl)-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)hydrazine(2–)]tetra­zinc(II) N,N-dimethyl­formamide tetra­solvate

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: cyclo-Tetrakis[μ-N-(2-hydroxybenzoyl)-N′-(2-hydroxy-3-methoxybenzylidene)hydrazine(2–)]tetrazinc(II) N,N-dimethylformamide tetrasolvate