(1,2-Disalicyloylhydrazine)hexakis(pyridine)dinickel(II) 1,2-disalicyloyl­hydrazine solvate

Chen, Y.-T.; Dou, J.-M.; Li, D.-C.; Wang, D.-Q.; Zhu, Y.-H.

doi:10.1107/S1600536807042936

(1,2-Disalicyloylhydrazine)hexakis(pyridine)dinickel(II) 1,2-disalicyloylhydrazine solvate

Y.-T. Chen, J.-M. Dou, D.-C. Li, D.-Q. Wang and Y.-H, Zhu

The title compound, [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]C₁₄H₁₂N₂O₄, is composed of the complex [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆] and a free ligand. Each nickel(II) coordination environment in the complex exhibits a distorted octahedral geometry. The dinuclear complex is centrosymmetric. The complex molecules are linked into one-dimensional chains via intermolecular O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042936/kj2063sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042936/kj2063Isup2.hkl Contains datablock I

CCDC reference: 663581

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.035
wR factor = 0.102
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        400 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.07

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

A large number of salicylhydrazine complexes have been prepared and studied. However, research on the complex with 1,2-disalicyloylhydrazine is limited to only one complex [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]2C₅H₅N (Chen & Liu, 2005). We have synthesized another new complex [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]C₁₄H₁₂N₂O₄, which has been characterized by X-ray diffraction and elemental analysis. Here we present the crystal structure of the title complex.

The title compound consists of the complex [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆] and a free ligand (1,2-disalicyloylhydrazine) (Fig. 1). The Ni complex is formed by one chelated ligand, two nickel ions and six pyridine molecules. The ligand is present as the tetranionic hexadentate ligand dsh^4- and is linked with two nickel atoms. Both the binuclear nickel complex and the free ligand exhibit crystallographic centrosymmetry. From the data shown in Table 1, we can see that each nickel ion resides in a slightly distorted octahedral coordination environment, consisting of three pyridine N, a phenolate O, a carbonyl O and a hydrazine N of the ligand. which construct the fused five-membered and six-membered rings with each nickel atom. The two unique chelate rings, one five-membered and one six-membered, are near to coplanar with an 3.9 (3) ° dihedral angle.

As illustrated in Fig 2, the alternation of complex and free ligand molecules is linked into one-dimensional chain by intermolecular O4—H4···O2 H-bonds (Table 2) along the [1 - 1 1] axis.

Related literature top

The complex [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·2C₅H₅N with 1,2-disalicyloylhydrazine was reported previously (Chen & Liu, 2005). In that complex, the salicyloylhydrazine ligand functions as a tetranionic hexadentate ligand.

Experimental top

A solution of Ni(OAc)₂H₂O (0.0996 g, 0.4 mmol) in methanol (10 ml) was added to 1,2-disalicyloylhydrazine (0.054 g, 0.2 mmol) in pyridine (10 ml). After stirring the solution for four hours at room temperature, a reddish solution was obtained. After the solution had been standing for two weeks, red block crystals suitable for X-ray diffraction appeared. Yield: 0.086 g, 39%. m.p.> 573 K. Anal. for C₅₈H₅₀N₁₀Ni₂O₈: Calc. C, 61.46; H, 4.41; N, 11.36; Found: C, 61.42; H, 4.47; N, 11.33%.

Structure description top

As illustrated in Fig 2, the alternation of complex and free ligand molecules is linked into one-dimensional chain by intermolecular O4—H4···O2 H-bonds (Table 2) along the [1 - 1 1] axis.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at 30% probability level and H atoms have been omitted for clarity. symm. (A) -x + 1, -y + 2, -z, (B) -x, -y + 1, -z + 1
	Fig. 2. Crystal packing of the title complex.

(1,2-Disalicyloylhydrazine)hexakis(pyridine)dinickel(II) 1,2-disalicyloylhydrazine solvate top

Crystal data top

[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·C₁₄H₁₂N₂O₄	Z = 1
M_r = 1132.50	F(000) = 588
Triclinic, P1	D_x = 1.399 Mg m⁻³
a = 10.615 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.097 (4) Å	Cell parameters from 2995 reflections
c = 12.094 (5) Å	θ = 2.2–25.4°
α = 72.230 (4)°	µ = 0.77 mm⁻¹
β = 85.285 (4)°	T = 298 K
γ = 82.876 (4)°	Block, red
V = 1344.7 (9) Å³	0.63 × 0.52 × 0.40 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4652 independent reflections
Radiation source: fine-focus sealed tube	3642 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.644, T_max = 0.749	k = −9→13
6973 measured reflections	l = −13→14

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.048P)² + 0.4895P] where P = (F_o² + 2F_c²)/3
4652 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·C₁₄H₁₂N₂O₄	γ = 82.876 (4)°
M_r = 1132.50	V = 1344.7 (9) Å³
Triclinic, P1	Z = 1
a = 10.615 (4) Å	Mo Kα radiation
b = 11.097 (4) Å	µ = 0.77 mm⁻¹
c = 12.094 (5) Å	T = 298 K
α = 72.230 (4)°	0.63 × 0.52 × 0.40 mm
β = 85.285 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4652 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3642 reflections with I > 2σ(I)
T_min = 0.644, T_max = 0.749	R_int = 0.024
6973 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.00	Δρ_max = 0.40 e Å⁻³
4652 reflections	Δρ_min = −0.28 e Å⁻³
352 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	0.58655 (3)	0.85566 (3)	0.16798 (3)	0.03193 (12)
N1	0.45229 (19)	1.05133 (19)	−0.00523 (17)	0.0279 (5)
N2	0.7511 (2)	0.9521 (2)	0.16127 (19)	0.0371 (5)
N3	0.5968 (2)	0.7776 (2)	0.34846 (18)	0.0381 (5)
N4	0.4278 (2)	0.7424 (2)	0.18095 (19)	0.0388 (5)
N5	0.0379 (3)	0.5115 (3)	0.5385 (2)	0.0567 (7)
H5	0.0788	0.4495	0.5882	0.068*
O1	0.46160 (17)	1.00370 (17)	0.19156 (14)	0.0366 (4)
O2	0.29489 (17)	1.27700 (16)	−0.11339 (15)	0.0358 (4)
O3	−0.0127 (2)	0.7197 (2)	0.4626 (2)	0.0711 (7)
O4	0.1637 (2)	0.43717 (19)	0.73076 (18)	0.0514 (5)
H4	0.2054	0.3913	0.7850	0.077*
C1	0.4151 (2)	1.0710 (2)	0.0945 (2)	0.0285 (6)
C2	0.3100 (2)	1.1727 (2)	0.0950 (2)	0.0306 (6)
C3	0.2541 (2)	1.2639 (2)	−0.0030 (2)	0.0327 (6)
C4	0.1496 (3)	1.3461 (3)	0.0180 (3)	0.0449 (7)
H4A	0.1106	1.4054	−0.0452	0.054*
C5	0.1028 (3)	1.3425 (3)	0.1281 (3)	0.0528 (8)
H5A	0.0329	1.3981	0.1381	0.063*
C6	0.1585 (3)	1.2572 (3)	0.2234 (3)	0.0506 (8)
H6	0.1284	1.2558	0.2982	0.061*
C7	0.2595 (3)	1.1742 (3)	0.2060 (2)	0.0419 (7)
H7	0.2965	1.1159	0.2708	0.050*
C8	0.8504 (3)	0.8988 (3)	0.2266 (3)	0.0517 (8)
H8	0.8428	0.8217	0.2839	0.062*
C9	0.9626 (3)	0.9511 (3)	0.2139 (3)	0.0656 (10)
H9	1.0285	0.9113	0.2627	0.079*
C10	0.9763 (3)	1.0626 (3)	0.1285 (3)	0.0642 (10)
H10	1.0528	1.0987	0.1157	0.077*
C11	0.8747 (3)	1.1202 (3)	0.0620 (3)	0.0642 (10)
H11	0.8801	1.1976	0.0046	0.077*
C12	0.7657 (3)	1.0625 (3)	0.0812 (3)	0.0488 (8)
H12	0.6974	1.1028	0.0355	0.059*
C13	0.5915 (3)	0.8589 (3)	0.4115 (3)	0.0541 (8)
H13	0.5839	0.9457	0.3730	0.065*
C14	0.5965 (4)	0.8199 (4)	0.5297 (3)	0.0730 (11)
H14	0.5928	0.8792	0.5704	0.088*
C15	0.6072 (4)	0.6928 (4)	0.5873 (3)	0.0803 (12)
H15	0.6117	0.6640	0.6677	0.096*
C16	0.6112 (4)	0.6085 (4)	0.5247 (3)	0.0689 (10)
H16	0.6187	0.5213	0.5619	0.083*
C17	0.6040 (3)	0.6544 (3)	0.4060 (3)	0.0485 (8)
H17	0.6042	0.5966	0.3642	0.058*
C18	0.3257 (3)	0.7548 (3)	0.2496 (3)	0.0502 (8)
H18	0.3233	0.8124	0.2920	0.060*
C19	0.2233 (3)	0.6862 (4)	0.2606 (3)	0.0644 (10)
H19	0.1534	0.6978	0.3094	0.077*
C20	0.2254 (4)	0.6018 (4)	0.2000 (4)	0.0723 (11)
H20	0.1574	0.5543	0.2065	0.087*
C21	0.3297 (4)	0.5875 (3)	0.1286 (3)	0.0666 (10)
H21	0.3337	0.5300	0.0861	0.080*
C22	0.4284 (3)	0.6599 (3)	0.1209 (3)	0.0499 (8)
H22	0.4984	0.6506	0.0716	0.060*
C23	0.0469 (3)	0.6322 (3)	0.5347 (3)	0.0493 (8)
C24	0.1349 (3)	0.6538 (3)	0.6131 (2)	0.0451 (7)
C25	0.1928 (3)	0.5585 (3)	0.7058 (3)	0.0442 (7)
C26	0.2772 (3)	0.5909 (3)	0.7717 (3)	0.0585 (9)
H26	0.3158	0.5283	0.8330	0.070*
C27	0.3040 (4)	0.7143 (4)	0.7470 (4)	0.0746 (11)
H27	0.3618	0.7347	0.7905	0.090*
C28	0.2452 (4)	0.8086 (4)	0.6577 (4)	0.0819 (12)
H28	0.2619	0.8926	0.6422	0.098*
C29	0.1627 (4)	0.7781 (3)	0.5924 (3)	0.0674 (10)
H29	0.1240	0.8422	0.5323	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0359 (2)	0.0282 (2)	0.02966 (19)	0.00429 (14)	−0.00713 (14)	−0.00721 (14)
N1	0.0280 (11)	0.0233 (11)	0.0314 (11)	0.0056 (8)	−0.0071 (9)	−0.0081 (9)
N2	0.0397 (13)	0.0301 (12)	0.0389 (12)	0.0012 (10)	−0.0122 (10)	−0.0058 (10)
N3	0.0445 (14)	0.0332 (13)	0.0328 (12)	−0.0011 (11)	−0.0077 (10)	−0.0040 (11)
N4	0.0379 (14)	0.0361 (13)	0.0397 (13)	−0.0001 (10)	−0.0056 (10)	−0.0076 (11)
N5	0.0685 (19)	0.0425 (15)	0.0532 (16)	0.0106 (14)	−0.0261 (13)	−0.0059 (13)
O1	0.0453 (11)	0.0360 (10)	0.0267 (9)	0.0095 (8)	−0.0078 (8)	−0.0106 (8)
O2	0.0401 (11)	0.0291 (10)	0.0345 (10)	0.0082 (8)	−0.0055 (8)	−0.0076 (8)
O3	0.0887 (19)	0.0464 (14)	0.0629 (15)	0.0190 (13)	−0.0272 (13)	0.0024 (12)
O4	0.0591 (14)	0.0373 (12)	0.0513 (12)	0.0072 (10)	−0.0215 (10)	−0.0036 (10)
C1	0.0285 (14)	0.0281 (14)	0.0303 (14)	−0.0005 (11)	−0.0041 (11)	−0.0108 (11)
C2	0.0300 (14)	0.0292 (14)	0.0348 (14)	−0.0016 (11)	−0.0051 (11)	−0.0125 (11)
C3	0.0321 (14)	0.0283 (14)	0.0387 (15)	−0.0009 (11)	−0.0028 (11)	−0.0123 (12)
C4	0.0406 (17)	0.0380 (17)	0.0510 (18)	0.0116 (13)	−0.0040 (14)	−0.0115 (14)
C5	0.0441 (18)	0.0492 (19)	0.064 (2)	0.0144 (15)	0.0028 (15)	−0.0234 (17)
C6	0.0505 (19)	0.057 (2)	0.0478 (17)	0.0094 (16)	0.0045 (14)	−0.0284 (16)
C7	0.0441 (17)	0.0445 (17)	0.0385 (15)	0.0057 (14)	−0.0060 (13)	−0.0172 (14)
C8	0.0464 (19)	0.0376 (17)	0.063 (2)	−0.0010 (14)	−0.0196 (16)	−0.0007 (15)
C9	0.048 (2)	0.052 (2)	0.091 (3)	−0.0017 (17)	−0.0284 (19)	−0.007 (2)
C10	0.050 (2)	0.062 (2)	0.083 (3)	−0.0165 (18)	−0.0067 (18)	−0.020 (2)
C11	0.074 (3)	0.049 (2)	0.062 (2)	−0.0234 (19)	−0.0175 (19)	0.0038 (17)
C12	0.054 (2)	0.0391 (17)	0.0490 (18)	−0.0059 (15)	−0.0206 (15)	−0.0022 (15)
C13	0.077 (2)	0.0435 (18)	0.0432 (17)	0.0012 (16)	−0.0187 (16)	−0.0131 (15)
C14	0.105 (3)	0.075 (3)	0.0423 (19)	0.002 (2)	−0.0203 (19)	−0.0234 (19)
C15	0.100 (3)	0.096 (3)	0.0348 (18)	−0.010 (3)	−0.0134 (19)	−0.001 (2)
C16	0.081 (3)	0.054 (2)	0.054 (2)	−0.009 (2)	−0.0116 (19)	0.0109 (19)
C17	0.0482 (19)	0.0418 (18)	0.0493 (18)	−0.0016 (14)	−0.0078 (14)	−0.0041 (15)
C18	0.0499 (19)	0.0480 (19)	0.0465 (17)	0.0000 (15)	0.0034 (15)	−0.0081 (15)
C19	0.050 (2)	0.061 (2)	0.067 (2)	−0.0070 (18)	0.0094 (17)	0.0012 (19)
C20	0.056 (2)	0.057 (2)	0.095 (3)	−0.0221 (19)	−0.008 (2)	−0.002 (2)
C21	0.071 (3)	0.053 (2)	0.084 (3)	−0.0117 (19)	−0.018 (2)	−0.026 (2)
C22	0.0498 (19)	0.0480 (19)	0.0546 (18)	−0.0010 (15)	−0.0078 (15)	−0.0195 (16)
C23	0.056 (2)	0.0427 (18)	0.0397 (16)	0.0099 (15)	0.0018 (14)	−0.0052 (14)
C24	0.0491 (18)	0.0384 (17)	0.0428 (16)	0.0048 (14)	0.0024 (14)	−0.0096 (14)
C25	0.0435 (17)	0.0400 (17)	0.0458 (17)	0.0075 (14)	0.0005 (13)	−0.0130 (14)
C26	0.059 (2)	0.054 (2)	0.063 (2)	0.0058 (17)	−0.0104 (17)	−0.0201 (18)
C27	0.077 (3)	0.067 (3)	0.092 (3)	−0.008 (2)	−0.011 (2)	−0.040 (2)
C28	0.094 (3)	0.049 (2)	0.105 (3)	−0.015 (2)	−0.004 (3)	−0.023 (2)
C29	0.084 (3)	0.042 (2)	0.069 (2)	−0.0011 (18)	−0.002 (2)	−0.0088 (18)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	1.974 (2)	C9—C10	1.364 (5)
Ni1—O2ⁱ	2.0455 (18)	C9—H9	0.9300
Ni1—O1	2.0549 (18)	C10—C11	1.370 (5)
Ni1—N3	2.095 (2)	C10—H10	0.9300
Ni1—N2	2.142 (2)	C11—C12	1.360 (4)
Ni1—N4	2.192 (2)	C11—H11	0.9300
N1—C1	1.312 (3)	C12—H12	0.9300
N1—N1ⁱ	1.410 (4)	C13—C14	1.365 (4)
N1—Ni1ⁱ	1.974 (2)	C13—H13	0.9300
N2—C12	1.327 (3)	C14—C15	1.365 (5)
N2—C8	1.335 (4)	C14—H14	0.9300
N3—C17	1.328 (4)	C15—C16	1.367 (5)
N3—C13	1.341 (4)	C15—H15	0.9300
N4—C18	1.330 (4)	C16—C17	1.374 (4)
N4—C22	1.331 (4)	C16—H16	0.9300
N5—C23	1.341 (4)	C17—H17	0.9300
N5—N5ⁱⁱ	1.378 (5)	C18—C19	1.378 (5)
N5—H5	0.8600	C18—H18	0.9300
O1—C1	1.284 (3)	C19—C20	1.352 (5)
O2—C3	1.339 (3)	C19—H19	0.9300
O2—Ni1ⁱ	2.0455 (18)	C20—C21	1.370 (5)
O3—C23	1.235 (3)	C20—H20	0.9300
O4—C25	1.356 (3)	C21—C22	1.378 (4)
O4—H4	0.8200	C21—H21	0.9300
C1—C2	1.485 (4)	C22—H22	0.9300
C2—C7	1.409 (4)	C23—C24	1.473 (4)
C2—C3	1.419 (4)	C24—C29	1.389 (4)
C3—C4	1.404 (4)	C24—C25	1.407 (4)
C4—C5	1.373 (4)	C25—C26	1.394 (4)
C4—H4A	0.9300	C26—C27	1.370 (5)
C5—C6	1.372 (4)	C26—H26	0.9300
C5—H5A	0.9300	C27—C28	1.382 (5)
C6—C7	1.371 (4)	C27—H27	0.9300
C6—H6	0.9300	C28—C29	1.362 (5)
C7—H7	0.9300	C28—H28	0.9300
C8—C9	1.366 (4)	C29—H29	0.9300
C8—H8	0.9300

N1ⁱ—Ni1—O2ⁱ	90.10 (8)	C9—C10—C11	118.3 (3)
N1ⁱ—Ni1—O1	79.56 (8)	C9—C10—H10	120.8
O2ⁱ—Ni1—O1	169.66 (7)	C11—C10—H10	120.8
N1ⁱ—Ni1—N3	169.09 (8)	C12—C11—C10	119.1 (3)
O2ⁱ—Ni1—N3	100.36 (8)	C12—C11—H11	120.5
O1—Ni1—N3	89.96 (8)	C10—C11—H11	120.5
N1ⁱ—Ni1—N2	93.18 (8)	N2—C12—C11	123.8 (3)
O2ⁱ—Ni1—N2	86.83 (8)	N2—C12—H12	118.1
O1—Ni1—N2	93.90 (9)	C11—C12—H12	118.1
N3—Ni1—N2	90.50 (9)	N3—C13—C14	123.0 (3)
N1ⁱ—Ni1—N4	89.88 (8)	N3—C13—H13	118.5
O2ⁱ—Ni1—N4	89.64 (8)	C14—C13—H13	118.5
O1—Ni1—N4	90.12 (9)	C15—C14—C13	119.1 (4)
N3—Ni1—N4	87.12 (9)	C15—C14—H14	120.5
N2—Ni1—N4	175.33 (8)	C13—C14—H14	120.5
C1—N1—N1ⁱ	113.2 (2)	C14—C15—C16	118.8 (3)
C1—N1—Ni1ⁱ	133.30 (17)	C14—C15—H15	120.6
N1ⁱ—N1—Ni1ⁱ	113.25 (19)	C16—C15—H15	120.6
C12—N2—C8	116.2 (3)	C15—C16—C17	119.0 (3)
C12—N2—Ni1	120.89 (18)	C15—C16—H16	120.5
C8—N2—Ni1	122.46 (19)	C17—C16—H16	120.5
C17—N3—C13	117.2 (3)	N3—C17—C16	122.9 (3)
C17—N3—Ni1	125.4 (2)	N3—C17—H17	118.6
C13—N3—Ni1	117.38 (19)	C16—C17—H17	118.6
C18—N4—C22	117.2 (3)	N4—C18—C19	122.9 (3)
C18—N4—Ni1	120.6 (2)	N4—C18—H18	118.6
C22—N4—Ni1	122.2 (2)	C19—C18—H18	118.6
C23—N5—N5ⁱⁱ	119.0 (3)	C20—C19—C18	119.4 (3)
C23—N5—H5	120.5	C20—C19—H19	120.3
N5ⁱⁱ—N5—H5	120.5	C18—C19—H19	120.3
C1—O1—Ni1	110.36 (15)	C19—C20—C21	118.8 (3)
C3—O2—Ni1ⁱ	124.83 (16)	C19—C20—H20	120.6
C25—O4—H4	109.5	C21—C20—H20	120.6
O1—C1—N1	123.2 (2)	C20—C21—C22	118.9 (3)
O1—C1—C2	118.8 (2)	C20—C21—H21	120.5
N1—C1—C2	118.0 (2)	C22—C21—H21	120.5
C7—C2—C3	117.7 (2)	N4—C22—C21	122.8 (3)
C7—C2—C1	115.1 (2)	N4—C22—H22	118.6
C3—C2—C1	127.3 (2)	C21—C22—H22	118.6
O2—C3—C4	118.1 (2)	O3—C23—N5	119.3 (3)
O2—C3—C2	124.4 (2)	O3—C23—C24	123.0 (3)
C4—C3—C2	117.5 (2)	N5—C23—C24	117.5 (3)
C5—C4—C3	122.5 (3)	C29—C24—C25	118.2 (3)
C5—C4—H4A	118.7	C29—C24—C23	116.8 (3)
C3—C4—H4A	118.7	C25—C24—C23	125.0 (3)
C6—C5—C4	120.5 (3)	O4—C25—C26	121.1 (3)
C6—C5—H5A	119.8	O4—C25—C24	119.5 (3)
C4—C5—H5A	119.8	C26—C25—C24	119.4 (3)
C7—C6—C5	118.5 (3)	C27—C26—C25	120.5 (3)
C7—C6—H6	120.8	C27—C26—H26	119.7
C5—C6—H6	120.8	C25—C26—H26	119.7
C6—C7—C2	123.4 (3)	C26—C27—C28	120.2 (4)
C6—C7—H7	118.3	C26—C27—H27	119.9
C2—C7—H7	118.3	C28—C27—H27	119.9
N2—C8—C9	123.7 (3)	C29—C28—C27	119.8 (4)
N2—C8—H8	118.1	C29—C28—H28	120.1
C9—C8—H8	118.1	C27—C28—H28	120.1
C10—C9—C8	118.9 (3)	C28—C29—C24	121.8 (4)
C10—C9—H9	120.6	C28—C29—H29	119.1
C8—C9—H9	120.6	C24—C29—H29	119.1

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱⁱⁱ	0.82	1.72	2.534 (3)	171

Symmetry code: (iii) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·C₁₄H₁₂N₂O₄
M_r	1132.50
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.615 (4), 11.097 (4), 12.094 (5)
α, β, γ (°)	72.230 (4), 85.285 (4), 82.876 (4)
V (Å³)	1344.7 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.63 × 0.52 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.644, 0.749
No. of measured, independent and observed [I > 2σ(I)] reflections	6973, 4652, 3642
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 1.00
No. of reflections	4652
No. of parameters	352
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.28

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected bond angles (º) top

N1ⁱ—Ni1—O2ⁱ	90.10 (8)	O1—Ni1—N2	93.90 (9)
N1ⁱ—Ni1—O1	79.56 (8)	N3—Ni1—N2	90.50 (9)
O2ⁱ—Ni1—O1	169.66 (7)	N1ⁱ—Ni1—N4	89.88 (8)
N1ⁱ—Ni1—N3	169.09 (8)	O2ⁱ—Ni1—N4	89.64 (8)
O2ⁱ—Ni1—N3	100.36 (8)	O1—Ni1—N4	90.12 (9)
O1—Ni1—N3	89.96 (8)	N3—Ni1—N4	87.12 (9)
N1ⁱ—Ni1—N2	93.18 (8)	N2—Ni1—N4	175.33 (8)
O2ⁱ—Ni1—N2	86.83 (8)

Symmetry code: (i) −x+1, −y+2, −z.