cyclo-Tetra­kis[μ-N-(2-hydroxy­benzo­yl)-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)hydrazinato(2−)]tetra­nickel(II) N,N-dimethyl­formamide tetra­solvate

Guan, G.; Gao, Y.; Wang, L.; Wang, T.

doi:10.1107/S1600536807048325

Retracted: cyclo-Tetrakis[μ-N-(2-hydroxybenzoyl)-N′-(2-hydroxy-3-methoxybenzylidene)hydrazinato(2−)]tetranickel(II) N,N-dimethylformamide tetrasolvate

The title compound, [Ni₄(C₁₅H₁₂N₂O₄)₄].₄C₃H₇NO, is isostructural with its Co^II and Zn^II analogues. The compound contains N-(2-hydroxybenzoyl)-N-(2-hydroxy-3-methoxybenzylidene)hydrazine anions and Ni^II cations linked into a tetrameric complex about a position of $\overline{4}$ point symmetry. Each Ni^II cation is pentacoordinate 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/S1600536807048325/bi2239sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048325/bi2239Isup2.hkl Contains datablock I

CCDC reference: 1259419

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R factor = 0.041
wR factor = 0.148
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O4      ..       6.81 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N2      ..       5.21 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         C3
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 Ni1         (2)       1.98

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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, [Ni₄(C₁₅H₁₂N₂O₄)₄].4C₃H₇NO, is isostructural with its Co^II (Gao et al., 2007a) and Zn^II (Gao et al., 2007b) analogues. As shown in Figure 1, each Ni^II cation is penta-coordinated by four O atoms and one N atom, forming a distorted square-based pyramidal geometry. The Ni—O bond lengths are in the range 1.936 (3)–2.277 (3) Å, and Ni—N = 1.951 (3) Å. The Ni^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

For the analogous Co^II and Zn^II complexes, see: Gao et al. (2007a,b).

Experimental top

A mixture of nickel(II) acetate (0.5 mmol) and N-(2-hydroxybenzoyl)-N-(2-hydroxy-3-methoxybenzylidene)-hydrazine in DMF (35 ml) was refluxed for 1 h then filtered. The filtrate was evaporated in the open flask to give green, block-shaped crystals in a yield of 22%. Elemental analysis calculated: C 51.32, H 4.51, N 9.98%; found: C 51.23, H 4.59, N 9.92%.

Structure description top

For the analogous Co^II and Zn^II complexes, see: Gao et al. (2007a,b).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Bruker, 2001).

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 + 1/4, -x + 3/4,-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)hydrazinato(2-)]tetranickel(II) N,N-dimethylformamide tetrasolvate top

Crystal data top

[Ni₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO	D_x = 1.452 Mg m⁻³
M_r = 1664.29	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3554 reflections
Hall symbol: -I 4ad	θ = 1.7–25.6°
a = 24.1627 (5) Å	µ = 1.05 mm⁻¹
c = 13.0428 (5) Å	T = 293 K
V = 7614.9 (5) Å³	Block, green
Z = 4	0.44 × 0.32 × 0.28 mm
F(000) = 3456

Data collection top

Bruker APEXII CCD diffractometer	3554 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
φ and ω scans	θ_max = 25.6°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −29→26
T_min = 0.641, T_max = 0.742	k = −26→29
19316 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.0789P)² + 9.3105P] where P = (F_o² + 2F_c²)/3
3554 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Ni₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO	Z = 4
M_r = 1664.29	Mo Kα radiation
Tetragonal, I4₁/a	µ = 1.05 mm⁻¹
a = 24.1627 (5) Å	T = 293 K
c = 13.0428 (5) Å	0.44 × 0.32 × 0.28 mm
V = 7614.9 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	3554 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2243 reflections with I > 2σ(I)
T_min = 0.641, T_max = 0.742	R_int = 0.062
19316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.148	H-atom parameters not refined
S = 1.00	Δρ_max = 0.41 e Å⁻³
3554 reflections	Δρ_min = −0.27 e Å⁻³
248 parameters

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
Ni1	0.51343 (2)	0.18333 (2)	0.46561 (3)	0.0409 (2)
C1	0.7168 (5)	0.1344 (6)	0.4322 (8)	0.216 (6)
H1A	0.6779	0.1285	0.4422	0.324*
H1B	0.7332	0.1016	0.4039	0.324*
H1C	0.7222	0.1648	0.3859	0.324*
C2	0.7902 (4)	0.1806 (4)	0.5196 (7)	0.143 (3)
H2A	0.8041	0.1883	0.5871	0.215*
H2B	0.7810	0.2147	0.4861	0.215*
H2C	0.8181	0.1616	0.4807	0.215*
C3	0.7206 (4)	0.1337 (4)	0.6169 (7)	0.115 (2)
H3	0.7379	0.1475	0.6753	0.138*
C4	0.6877 (3)	0.3233 (3)	0.2908 (5)	0.125 (3)
H4A	0.7052	0.3548	0.3216	0.187*
H4B	0.6749	0.3329	0.2234	0.187*
H4C	0.7138	0.2935	0.2861	0.187*
C5	0.65107 (17)	0.29037 (18)	0.4539 (3)	0.0507 (10)
C6	0.69529 (19)	0.3068 (2)	0.5121 (4)	0.0635 (13)
H6	0.7229	0.3284	0.4828	0.076*
C7	0.6993 (2)	0.2913 (2)	0.6157 (4)	0.0703 (14)
H7	0.7296	0.3027	0.6543	0.084*
C8	0.6593 (2)	0.2599 (2)	0.6597 (4)	0.0662 (13)
H8	0.6619	0.2509	0.7289	0.079*
C9	0.61399 (17)	0.24100 (17)	0.6018 (3)	0.0500 (10)
C10	0.60984 (16)	0.25627 (17)	0.4954 (3)	0.0458 (10)
C11	0.57372 (18)	0.20921 (17)	0.6556 (3)	0.0519 (10)
H11	0.5778	0.2048	0.7260	0.062*
C12	0.45681 (17)	0.13432 (17)	0.6187 (3)	0.0502 (10)
C13	0.41377 (18)	0.10458 (18)	0.6752 (4)	0.0546 (11)
C14	0.3737 (2)	0.07678 (19)	0.6201 (5)	0.0713 (14)
H14	0.3753	0.0761	0.5488	0.086*
C15	0.3308 (2)	0.0498 (2)	0.6711 (7)	0.096 (2)
H15	0.3037	0.0309	0.6345	0.116*
C16	0.3291 (3)	0.0515 (3)	0.7802 (7)	0.101 (2)
H16	0.3000	0.0344	0.8142	0.121*
C17	0.3682 (3)	0.0772 (3)	0.8349 (6)	0.095 (2)
H17	0.3664	0.0772	0.9062	0.115*
C18	0.4115 (2)	0.1039 (2)	0.7853 (4)	0.0702 (14)
N1	0.7419 (3)	0.1467 (3)	0.5271 (5)	0.122 (2)
N2	0.53184 (15)	0.18618 (14)	0.6112 (3)	0.0504 (9)
N3	0.49535 (15)	0.15758 (15)	0.6751 (3)	0.0550 (9)
O1	0.6796 (3)	0.1047 (3)	0.6286 (5)	0.169 (3)
O2	0.64209 (12)	0.30661 (13)	0.3519 (2)	0.0618 (8)
O3	0.56721 (11)	0.24110 (12)	0.4338 (2)	0.0483 (7)
O4	0.45500 (12)	0.13623 (12)	0.5176 (2)	0.0553 (8)
O5	0.44927 (19)	0.12902 (19)	0.8454 (3)	0.0966 (13)
H5	0.4730	0.1436	0.8094	0.145*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0523 (3)	0.0493 (3)	0.0210 (3)	−0.0025 (2)	−0.0030 (2)	0.0027 (2)
C1	0.232 (12)	0.307 (16)	0.110 (9)	−0.076 (12)	0.016 (8)	−0.032 (9)
C2	0.118 (6)	0.146 (7)	0.166 (9)	0.000 (6)	0.011 (6)	0.018 (6)
C3	0.103 (6)	0.138 (7)	0.103 (6)	0.006 (5)	0.008 (5)	−0.011 (5)
C4	0.104 (5)	0.188 (8)	0.082 (5)	−0.057 (5)	0.002 (4)	0.050 (5)
C5	0.055 (3)	0.059 (3)	0.038 (2)	−0.001 (2)	−0.0010 (19)	0.0006 (19)
C6	0.058 (3)	0.073 (3)	0.059 (3)	−0.013 (2)	−0.005 (2)	0.002 (2)
C7	0.064 (3)	0.084 (3)	0.063 (3)	−0.019 (3)	−0.016 (3)	0.001 (3)
C8	0.069 (3)	0.087 (3)	0.042 (3)	−0.004 (3)	−0.016 (2)	0.002 (2)
C9	0.055 (2)	0.057 (3)	0.037 (2)	−0.0041 (19)	−0.0067 (19)	0.0004 (19)
C10	0.049 (2)	0.053 (2)	0.036 (2)	0.0001 (18)	−0.0048 (18)	−0.0029 (18)
C11	0.063 (3)	0.064 (3)	0.030 (2)	−0.003 (2)	−0.012 (2)	0.0046 (19)
C12	0.059 (3)	0.052 (2)	0.040 (2)	0.007 (2)	0.000 (2)	0.0116 (19)
C13	0.059 (3)	0.051 (2)	0.054 (3)	0.005 (2)	0.003 (2)	0.014 (2)
C14	0.062 (3)	0.063 (3)	0.089 (4)	0.000 (2)	0.002 (3)	0.021 (3)
C15	0.066 (3)	0.079 (4)	0.145 (7)	−0.009 (3)	−0.002 (4)	0.031 (4)
C16	0.083 (4)	0.088 (4)	0.132 (7)	−0.001 (4)	0.032 (4)	0.040 (4)
C17	0.100 (5)	0.095 (4)	0.092 (5)	0.008 (4)	0.040 (4)	0.030 (4)
C18	0.077 (3)	0.076 (3)	0.058 (3)	0.007 (3)	0.018 (3)	0.017 (3)
N1	0.102 (4)	0.171 (6)	0.092 (5)	−0.004 (4)	0.018 (4)	−0.010 (4)
N2	0.060 (2)	0.061 (2)	0.0303 (19)	−0.0001 (17)	−0.0012 (16)	0.0080 (16)
N3	0.061 (2)	0.071 (2)	0.0333 (19)	−0.0056 (19)	−0.0004 (17)	0.0076 (17)
O1	0.149 (5)	0.217 (7)	0.143 (6)	−0.022 (5)	0.024 (5)	0.015 (5)
O2	0.0626 (19)	0.080 (2)	0.0431 (18)	−0.0146 (16)	0.0003 (14)	0.0138 (16)
O3	0.0555 (16)	0.0626 (17)	0.0268 (14)	−0.0049 (13)	−0.0038 (12)	0.0038 (13)
O4	0.0681 (19)	0.0615 (18)	0.0364 (17)	−0.0058 (14)	−0.0051 (14)	0.0039 (13)
O5	0.123 (3)	0.124 (3)	0.043 (2)	−0.027 (3)	0.015 (2)	0.009 (2)

Geometric parameters (Å, º) top

Ni1—O4	1.936 (3)	C7—H7	0.930
Ni1—O3	1.952 (3)	C8—C9	1.408 (6)
Ni1—N2	1.951 (3)	C8—H8	0.930
Ni1—O3ⁱ	2.022 (3)	C9—C11	1.425 (6)
Ni1—O2ⁱ	2.277 (3)	C9—C10	1.440 (6)
C1—N1	1.410 (11)	C10—O3	1.357 (5)
C1—H1A	0.960	C11—N2	1.292 (5)
C1—H1B	0.960	C11—H11	0.930
C1—H1C	0.960	C12—N3	1.313 (5)
C2—N1	1.429 (10)	C12—O4	1.320 (5)
C2—H2A	0.960	C12—C13	1.463 (6)
C2—H2B	0.960	C13—C14	1.380 (7)
C2—H2C	0.960	C13—C18	1.438 (7)
C3—O1	1.224 (9)	C14—C15	1.393 (7)
C3—N1	1.318 (10)	C14—H14	0.930
C3—H3	0.930	C15—C16	1.423 (10)
C4—O2	1.418 (6)	C15—H15	0.930
C4—H4A	0.960	C16—C17	1.337 (9)
C4—H4B	0.960	C16—H16	0.930
C4—H4C	0.960	C17—C18	1.389 (7)
C5—C6	1.369 (6)	C17—H17	0.930
C5—O2	1.404 (5)	C18—O5	1.347 (6)
C5—C10	1.401 (6)	N2—N3	1.396 (5)
C6—C7	1.406 (7)	O2—Ni1ⁱⁱ	2.277 (3)
C6—H6	0.930	O3—Ni1ⁱⁱ	2.022 (3)
C7—C8	1.356 (7)	O5—H5	0.820

O4—Ni1—O3	168.64 (12)	C8—C9—C10	119.2 (4)
O4—Ni1—N2	81.15 (13)	C11—C9—C10	124.4 (4)
O3—Ni1—N2	91.71 (13)	O3—C10—C5	118.1 (4)
O4—Ni1—O3ⁱ	97.99 (12)	O3—C10—C9	123.7 (4)
O3—Ni1—O3ⁱ	88.71 (11)	C5—C10—C9	118.2 (4)
N2—Ni1—O3ⁱ	177.17 (13)	N2—C11—C9	123.1 (4)
O4—Ni1—O2ⁱ	89.95 (12)	N2—C11—H11	118.4
O3—Ni1—O2ⁱ	100.67 (12)	C9—C11—H11	118.4
N2—Ni1—O2ⁱ	107.47 (13)	N3—C12—O4	124.6 (4)
O3ⁱ—Ni1—O2ⁱ	75.18 (10)	N3—C12—C13	115.6 (4)
N1—C1—H1A	109.5	O4—C12—C13	119.8 (4)
N1—C1—H1B	109.5	C14—C13—C18	119.2 (5)
H1A—C1—H1B	109.5	C14—C13—C12	118.4 (4)
N1—C1—H1C	109.5	C18—C13—C12	122.4 (4)
H1A—C1—H1C	109.5	C13—C14—C15	120.0 (6)
H1B—C1—H1C	109.5	C13—C14—H14	120.0
N1—C2—H2A	109.5	C15—C14—H14	120.0
N1—C2—H2B	109.5	C14—C15—C16	119.0 (6)
H2A—C2—H2B	109.5	C14—C15—H15	120.5
N1—C2—H2C	109.5	C16—C15—H15	120.5
H2A—C2—H2C	109.5	C17—C16—C15	121.8 (6)
H2B—C2—H2C	109.5	C17—C16—H16	119.1
O1—C3—N1	124.3 (9)	C15—C16—H16	119.1
O1—C3—H3	117.8	C16—C17—C18	119.9 (7)
N1—C3—H3	117.8	C16—C17—H17	120.1
O2—C4—H4A	109.5	C18—C17—H17	120.1
O2—C4—H4B	109.5	O5—C18—C17	116.6 (6)
H4A—C4—H4B	109.5	O5—C18—C13	123.4 (4)
O2—C4—H4C	109.5	C17—C18—C13	120.0 (6)
H4A—C4—H4C	109.5	C3—N1—C1	124.2 (8)
H4B—C4—H4C	109.5	C3—N1—C2	121.1 (8)
C6—C5—O2	124.4 (4)	C1—N1—C2	114.4 (8)
C6—C5—C10	120.8 (4)	C11—N2—N3	116.1 (3)
O2—C5—C10	114.8 (4)	C11—N2—Ni1	129.1 (3)
C5—C6—C7	120.6 (4)	N3—N2—Ni1	114.8 (3)
C5—C6—H6	119.7	C12—N3—N2	109.0 (3)
C7—C6—H6	119.7	C5—O2—C4	119.5 (4)
C8—C7—C6	120.4 (4)	C5—O2—Ni1ⁱⁱ	111.2 (2)
C8—C7—H7	119.8	C4—O2—Ni1ⁱⁱ	122.3 (3)
C6—C7—H7	119.8	C10—O3—Ni1	125.0 (3)
C7—C8—C9	120.6 (4)	C10—O3—Ni1ⁱⁱ	120.2 (2)
C7—C8—H8	119.7	Ni1—O3—Ni1ⁱⁱ	113.04 (13)
C9—C8—H8	119.7	C12—O4—Ni1	110.3 (3)
C8—C9—C11	116.3 (4)	C18—O5—H5	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N3	0.82	1.86	2.579 (5)	145

Experimental details

Crystal data
Chemical formula	[Ni₄(C₁₅H₁₂N₂O₄)₄]·4C₃H₇NO
M_r	1664.29
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	24.1627 (5), 13.0428 (5)
V (Å³)	7614.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.44 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.641, 0.742
No. of measured, independent and observed [I > 2σ(I)] reflections	19316, 3554, 2243
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.148, 1.00
No. of reflections	3554
No. of parameters	248
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N3	0.82	1.86	2.579 (5)	144.9

Format		BIBTeX
		EndNote
		RefMan
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		Medline
		CIF
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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)hydrazinato(2−)]tetra­nickel(II) N,N-dimethyl­formamide tetra­solvate

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: cyclo-Tetrakis[μ-N-(2-hydroxybenzoyl)-N′-(2-hydroxy-3-methoxybenzylidene)hydrazinato(2−)]tetranickel(II) N,N-dimethylformamide tetrasolvate