[μ-1,2-Disalicyloylhydrazine(2–)-κ3N,O,O′:κ3N′,O′′,O′′′]bis­[tripyridine­nickel(II)] pyridine disolvate

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

doi:10.1107/S1600536807033582

[μ-1,2-Disalicyloylhydrazine(2–)-κ³N,O,O′:κ³N′,O′′,O′′′]bis[tripyridinenickel(II)] pyridine disolvate

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

The title complex, [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·2C₅H₅N, is a polymorph of a previously reported compound [Chen & Liu (2005). Chin. J. Inorg. Chem. 21, 15–20]. The 1,2-disalicyloylhydrazine ligand lies on an inversion center and coordinates to two Ni^II atoms. Each Ni^II atom is octahedrally coordinated by a phenolate O atom, a carbonyl O atom and a hydrazine N atom of the ligand and three pyridine N atoms.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033582/hy2070sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033582/hy2070Isup2.hkl Contains datablock I

CCDC reference: 648656

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.053
wR factor = 0.152
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     200.00 A   3 

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for         N5
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C24
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C26
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C23
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C25
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C27
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.12
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        102

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Recently, we have synthesized two metallacrowns using N-acyl-3-hydroxy-2-naphthalenecarbohydrazide (Dou et al., 2006). As an extension of our work on the structural characterization of naphthalenecarbohydrazide compounds, the title complex, (I), was synthesized and characterized by X-ray diffraction.

The complex (I) (space group I4₁/a) is a polymorph of the compound (space group P2₁/c) previously reported by Chen & Liu (2005), with the same formula [Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆].2C₅H₅N. The complex molecule of (I) lies on an inversion center (Fig. 1). The 1,2-disalicyloylhydrazine molecule acts as a hexadentate tetravalent anionic ligand linking two Ni^II atoms. The iminophenolate group (O2 and N1) and the iminoacyl group (O1ⁱ and N1; symmetry code: (i) 1 - x, -y, -z) of the ligand are coordinated to the Ni1 atom to form six-membered and five-membered chelating rings, respectively, with a dihedral angle of 1.7 (4)°. Besides the above three atoms coordinated to the Ni1 atom, there are other three pyridine N atoms bonded to the Ni1 atom. So the coordination geometry of the Ni1 atom can be described as an N₄O₂ octahedron. As shown in Table 1, the axial Ni—N distances are longer than the equatorial Ni—N and Ni—O distances, which shows the Ni^II atom in a distorted octahedral geometry. This typical Jahn-Teller elongation has been observed in the other complexes (Kwak et al., 2000).

Related literature top

For related literature, see: Chen & Liu (2005); Dou et al. (2006); Kwak et al. (2000).

Experimental top

A solution of Ni(CH₃CO₂)₂.H₂O (0.100 g, 0.4 mmol) in methanol (10 ml) was added to the mixture of 1,2-disalicyloylhydrazine (0.054 g, 0.2 mmol) and sodium hydroxide (0.032 g, 0.8 mmol) in pyridine (10 ml). A red solution was generated after stirring for 2 h at room temperature. The solution was allowed to stand for 2 weeks, whereupon red needle crystals were obtained (0.070 g, yield 34%).

Structure description top

For related literature, see: Chen & Liu (2005); Dou et al. (2006); Kwak et al. (2000).

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) 1 - x, -y, -z.]

[µ-1,2-Disalicyloylhydrazine(2-)- κ³N,O,O':κ³N',O'',O''']bis[tripyridinenickel(II)] pyridine disolvate top

Crystal data top

[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·2C₅H₅N	D_x = 1.292 Mg m⁻³
M_r = 1018.44	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3046 reflections
Hall symbol: -I 4ad	θ = 2.2–21.5°
a = 27.040 (2) Å	µ = 0.77 mm⁻¹
c = 14.3178 (18) Å	T = 298 K
V = 10468.6 (17) Å³	Block, red
Z = 8	0.34 × 0.23 × 0.20 mm
F(000) = 4240

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4609 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
φ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→32
T_min = 0.779, T_max = 0.861	k = −32→30
21466 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
4609 reflections	(Δ/σ)_max < 0.001
316 parameters	Δρ_max = 0.31 e Å⁻³
102 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·2C₅H₅N	Z = 8
M_r = 1018.44	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.77 mm⁻¹
a = 27.040 (2) Å	T = 298 K
c = 14.3178 (18) Å	0.34 × 0.23 × 0.20 mm
V = 10468.6 (17) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4609 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2743 reflections with I > 2σ(I)
T_min = 0.779, T_max = 0.861	R_int = 0.064
21466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	102 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
4609 reflections	Δρ_min = −0.43 e Å⁻³
316 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.

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

	x	y	z	U_iso*/U_eq
Ni1	0.547168 (18)	0.061356 (19)	0.07264 (4)	0.0430 (2)
N1	0.50175 (11)	0.00672 (11)	0.0474 (2)	0.0402 (8)
N2	0.49003 (13)	0.11803 (14)	0.0520 (3)	0.0576 (9)
N3	0.61032 (12)	0.01068 (13)	0.0880 (3)	0.0498 (9)
N4	0.59618 (12)	0.12023 (12)	0.0881 (2)	0.0465 (9)
N5	0.7088 (6)	0.3732 (4)	0.3455 (7)	0.175 (4)
O1	0.44541 (9)	−0.05583 (9)	0.07017 (18)	0.0443 (7)
O2	0.53200 (10)	0.05767 (9)	0.2084 (2)	0.0492 (7)
C1	0.47284 (14)	−0.02083 (14)	0.1014 (3)	0.0384 (9)
C2	0.47115 (14)	−0.00872 (14)	0.2032 (3)	0.0381 (9)
C3	0.49896 (14)	0.02951 (14)	0.2477 (3)	0.0420 (10)
C4	0.48975 (16)	0.03587 (16)	0.3447 (3)	0.0501 (11)
H4	0.5068	0.0607	0.3761	0.060*
C5	0.45740 (16)	0.00756 (17)	0.3939 (3)	0.0533 (11)
H5	0.4528	0.0135	0.4572	0.064*
C6	0.43109 (17)	−0.03022 (17)	0.3502 (3)	0.0565 (12)
H6	0.4094	−0.0502	0.3836	0.068*
C7	0.43824 (14)	−0.03701 (16)	0.2565 (3)	0.0468 (10)
H7	0.4203	−0.0617	0.2266	0.056*
C8	0.4812 (2)	0.1372 (2)	−0.0297 (5)	0.0941 (16)
H8	0.4977	0.1238	−0.0807	0.113*
C9	0.4494 (2)	0.1757 (3)	−0.0462 (5)	0.1082 (17)
H9	0.4458	0.1884	−0.1062	0.130*
C10	0.4239 (2)	0.1948 (2)	0.0245 (5)	0.1061 (17)
H10	0.4014	0.2204	0.0154	0.127*
C11	0.4319 (3)	0.1754 (3)	0.1097 (5)	0.1206 (19)
H11	0.4149	0.1876	0.1613	0.145*
C12	0.4651 (2)	0.1376 (2)	0.1203 (5)	0.1042 (17)
H12	0.4702	0.1251	0.1801	0.125*
C13	0.61964 (19)	−0.02483 (18)	0.0272 (4)	0.0725 (15)
H13	0.5992	−0.0278	−0.0247	0.087*
C14	0.6578 (2)	−0.0574 (2)	0.0369 (5)	0.0954 (19)
H14	0.6626	−0.0819	−0.0077	0.115*
C15	0.6881 (2)	−0.0543 (3)	0.1102 (6)	0.101 (2)
H15	0.7142	−0.0763	0.1176	0.121*
C16	0.6796 (2)	−0.0176 (3)	0.1742 (5)	0.109 (2)
H16	0.6998	−0.0140	0.2264	0.131*
C17	0.6407 (2)	0.0136 (2)	0.1591 (4)	0.0812 (17)
H17	0.6354	0.0388	0.2023	0.097*
C18	0.62427 (18)	0.13505 (18)	0.0177 (4)	0.0663 (14)
H18	0.6214	0.1184	−0.0389	0.080*
C19	0.65742 (19)	0.17364 (19)	0.0229 (4)	0.0746 (15)
H19	0.6760	0.1828	−0.0289	0.090*
C20	0.66227 (19)	0.19768 (18)	0.1045 (4)	0.0708 (15)
H20	0.6844	0.2239	0.1104	0.085*
C21	0.6339 (2)	0.18282 (19)	0.1793 (4)	0.0796 (16)
H21	0.6365	0.1987	0.2368	0.096*
C22	0.60200 (19)	0.14440 (18)	0.1675 (3)	0.0679 (14)
H22	0.5831	0.1345	0.2185	0.081*
C23	0.6591 (6)	0.3744 (4)	0.3440 (8)	0.159 (4)
H23	0.6407	0.3514	0.3775	0.191*
C24	0.6371 (4)	0.4087 (7)	0.2945 (11)	0.185 (6)
H24	0.6029	0.4119	0.2979	0.223*
C25	0.6630 (7)	0.4396 (4)	0.2384 (10)	0.166 (6)
H25	0.6465	0.4614	0.1990	0.199*
C26	0.7111 (7)	0.4387 (4)	0.2398 (8)	0.177 (5)
H26	0.7291	0.4609	0.2036	0.213*
C27	0.7346 (3)	0.4057 (5)	0.2934 (11)	0.156 (4)
H27	0.7690	0.4053	0.2948	0.187*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0436 (3)	0.0457 (3)	0.0396 (3)	−0.0082 (2)	−0.0003 (2)	−0.0042 (2)
N1	0.0420 (18)	0.048 (2)	0.0302 (17)	−0.0042 (16)	0.0010 (15)	−0.0027 (15)
N2	0.056 (2)	0.060 (2)	0.058 (2)	0.0037 (18)	0.0054 (18)	−0.0014 (18)
N3	0.047 (2)	0.049 (2)	0.053 (2)	−0.0053 (17)	−0.0005 (18)	0.0004 (18)
N4	0.049 (2)	0.044 (2)	0.047 (2)	−0.0061 (16)	−0.0016 (17)	−0.0021 (17)
N5	0.249 (13)	0.146 (8)	0.131 (8)	0.039 (9)	−0.048 (8)	−0.037 (6)
O1	0.0460 (16)	0.0466 (16)	0.0402 (17)	−0.0145 (13)	0.0017 (12)	−0.0025 (13)
O2	0.0572 (18)	0.0501 (17)	0.0403 (17)	−0.0147 (15)	0.0006 (13)	−0.0016 (13)
C1	0.037 (2)	0.041 (2)	0.037 (2)	0.0008 (18)	0.0024 (17)	0.0012 (18)
C2	0.039 (2)	0.041 (2)	0.034 (2)	0.0028 (18)	−0.0001 (17)	0.0000 (17)
C3	0.041 (2)	0.044 (2)	0.041 (2)	0.0062 (19)	−0.0039 (19)	−0.0007 (19)
C4	0.056 (3)	0.055 (3)	0.039 (3)	0.002 (2)	0.000 (2)	−0.010 (2)
C5	0.057 (3)	0.069 (3)	0.034 (2)	0.004 (2)	0.006 (2)	0.000 (2)
C6	0.055 (3)	0.064 (3)	0.050 (3)	−0.006 (2)	0.012 (2)	0.003 (2)
C7	0.041 (2)	0.055 (3)	0.045 (3)	−0.005 (2)	0.0049 (19)	−0.001 (2)
C8	0.105 (3)	0.096 (3)	0.081 (3)	0.040 (3)	0.003 (3)	0.006 (3)
C9	0.119 (4)	0.110 (4)	0.096 (4)	0.045 (3)	−0.003 (3)	0.010 (3)
C10	0.111 (4)	0.104 (4)	0.104 (4)	0.046 (3)	0.003 (3)	0.010 (3)
C11	0.133 (4)	0.125 (4)	0.105 (4)	0.058 (3)	0.022 (3)	0.004 (3)
C12	0.113 (4)	0.114 (4)	0.086 (4)	0.056 (3)	0.020 (3)	0.013 (3)
C13	0.085 (4)	0.067 (3)	0.066 (4)	0.023 (3)	−0.008 (3)	−0.007 (3)
C14	0.112 (5)	0.091 (4)	0.083 (5)	0.044 (4)	0.014 (4)	0.005 (3)
C15	0.071 (4)	0.114 (6)	0.118 (6)	0.035 (4)	0.003 (4)	0.026 (5)
C16	0.085 (5)	0.109 (5)	0.133 (7)	0.011 (4)	−0.054 (4)	0.001 (5)
C17	0.075 (4)	0.075 (4)	0.093 (4)	0.008 (3)	−0.031 (3)	−0.009 (3)
C18	0.070 (3)	0.070 (3)	0.059 (3)	−0.021 (3)	0.012 (3)	−0.006 (3)
C19	0.070 (3)	0.072 (4)	0.082 (4)	−0.025 (3)	0.011 (3)	0.002 (3)
C20	0.063 (3)	0.055 (3)	0.094 (4)	−0.020 (3)	−0.011 (3)	0.004 (3)
C21	0.088 (4)	0.071 (4)	0.080 (4)	−0.033 (3)	−0.006 (3)	−0.019 (3)
C22	0.076 (3)	0.071 (3)	0.056 (3)	−0.028 (3)	0.007 (3)	−0.012 (3)
C23	0.184 (11)	0.172 (11)	0.121 (9)	0.005 (10)	0.069 (9)	0.017 (7)
C24	0.128 (9)	0.245 (17)	0.184 (14)	0.104 (11)	−0.004 (8)	−0.064 (11)
C25	0.223 (15)	0.094 (7)	0.181 (13)	0.054 (9)	−0.090 (12)	−0.019 (7)
C26	0.257 (16)	0.071 (6)	0.204 (12)	−0.036 (9)	−0.035 (11)	0.032 (6)
C27	0.131 (8)	0.101 (7)	0.235 (14)	−0.010 (7)	−0.024 (9)	−0.058 (8)

Geometric parameters (Å, º) top

Ni1—N1	1.955 (3)	C9—H9	0.9300
Ni1—O2	1.989 (3)	C10—C11	1.346 (9)
Ni1—O1ⁱ	2.060 (3)	C10—H10	0.9300
Ni1—N4	2.083 (3)	C11—C12	1.369 (8)
Ni1—N2	2.196 (4)	C11—H11	0.9300
Ni1—N3	2.201 (3)	C12—H12	0.9300
N1—C1	1.328 (5)	C13—C14	1.363 (7)
N1—N1ⁱ	1.409 (6)	C13—H13	0.9300
N2—C12	1.300 (6)	C14—C15	1.335 (8)
N2—C8	1.301 (6)	C14—H14	0.9300
N3—C17	1.310 (6)	C15—C16	1.371 (9)
N3—C13	1.320 (6)	C15—H15	0.9300
N4—C22	1.320 (5)	C16—C17	1.366 (8)
N4—C18	1.325 (5)	C16—H16	0.9300
N5—C23	1.345 (11)	C17—H17	0.9300
N5—C27	1.348 (11)	C18—C19	1.378 (6)
O1—C1	1.283 (4)	C18—H18	0.9300
O1—Ni1ⁱ	2.060 (3)	C19—C20	1.344 (7)
O2—C3	1.302 (4)	C19—H19	0.9300
C1—C2	1.495 (5)	C20—C21	1.378 (7)
C2—C7	1.399 (5)	C20—H20	0.9300
C2—C3	1.428 (5)	C21—C22	1.361 (6)
C3—C4	1.421 (5)	C21—H21	0.9300
C4—C5	1.359 (5)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.310 (11)
C5—C6	1.393 (6)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.354 (12)
C6—C7	1.368 (6)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.30 (3)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.371 (7)	C26—C27	1.337 (10)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.329 (8)	C27—H27	0.9300

N1—Ni1—O2	90.75 (11)	C8—C9—H9	120.4
N1—Ni1—O1ⁱ	79.81 (11)	C9—C10—C11	117.1 (7)
O2—Ni1—O1ⁱ	170.55 (10)	C9—C10—H10	121.4
N1—Ni1—N4	175.46 (13)	C11—C10—H10	121.4
O2—Ni1—N4	93.76 (12)	C10—C11—C12	119.8 (7)
O1ⁱ—Ni1—N4	95.68 (12)	C10—C11—H11	120.1
N1—Ni1—N2	93.47 (13)	C12—C11—H11	120.1
O2—Ni1—N2	91.23 (13)	N2—C12—C11	124.1 (6)
O1ⁱ—Ni1—N2	89.17 (13)	N2—C12—H12	118.0
N4—Ni1—N2	85.91 (13)	C11—C12—H12	118.0
N1—Ni1—N3	92.03 (13)	N3—C13—C14	123.2 (5)
O2—Ni1—N3	91.77 (12)	N3—C13—H13	118.4
O1ⁱ—Ni1—N3	88.77 (12)	C14—C13—H13	118.4
N4—Ni1—N3	88.37 (12)	C15—C14—C13	120.3 (6)
N2—Ni1—N3	173.70 (13)	C15—C14—H14	119.8
C1—N1—N1ⁱ	112.1 (4)	C13—C14—H14	119.8
C1—N1—Ni1	133.4 (3)	C14—C15—C16	117.9 (6)
N1ⁱ—N1—Ni1	114.5 (3)	C14—C15—H15	121.1
C12—N2—C8	114.8 (5)	C16—C15—H15	121.1
C12—N2—Ni1	123.2 (4)	C17—C16—C15	118.1 (6)
C8—N2—Ni1	121.9 (4)	C17—C16—H16	120.9
C17—N3—C13	115.9 (4)	C15—C16—H16	120.9
C17—N3—Ni1	121.8 (3)	N3—C17—C16	124.6 (6)
C13—N3—Ni1	122.3 (3)	N3—C17—H17	117.7
C22—N4—C18	115.9 (4)	C16—C17—H17	117.7
C22—N4—Ni1	123.1 (3)	N4—C18—C19	124.1 (5)
C18—N4—Ni1	121.0 (3)	N4—C18—H18	117.9
C23—N5—C27	119.5 (9)	C19—C18—H18	117.9
C1—O1—Ni1ⁱ	110.1 (2)	C20—C19—C18	118.5 (5)
C3—O2—Ni1	126.4 (2)	C20—C19—H19	120.7
O1—C1—N1	123.5 (4)	C18—C19—H19	120.7
O1—C1—C2	118.9 (3)	C19—C20—C21	118.7 (5)
N1—C1—C2	117.6 (3)	C19—C20—H20	120.6
C7—C2—C3	119.2 (4)	C21—C20—H20	120.6
C7—C2—C1	115.5 (3)	C22—C21—C20	118.6 (5)
C3—C2—C1	125.3 (3)	C22—C21—H21	120.7
O2—C3—C4	118.2 (4)	C20—C21—H21	120.7
O2—C3—C2	126.3 (4)	N4—C22—C21	124.1 (5)
C4—C3—C2	115.5 (4)	N4—C22—H22	117.9
C5—C4—C3	123.4 (4)	C21—C22—H22	117.9
C5—C4—H4	118.3	C24—C23—N5	118.7 (9)
C3—C4—H4	118.3	C24—C23—H23	120.6
C4—C5—C6	120.6 (4)	N5—C23—H23	120.6
C4—C5—H5	119.7	C23—C24—C25	121.5 (10)
C6—C5—H5	119.7	C23—C24—H24	119.3
C7—C6—C5	117.8 (4)	C25—C24—H24	119.3
C7—C6—H6	121.1	C26—C25—C24	119.8 (10)
C5—C6—H6	121.1	C26—C25—H25	120.1
C6—C7—C2	123.4 (4)	C24—C25—H25	120.1
C6—C7—H7	118.3	C25—C26—C27	119.7 (9)
C2—C7—H7	118.3	C25—C26—H26	120.1
N2—C8—C9	124.9 (6)	C27—C26—H26	120.1
N2—C8—H8	117.5	C26—C27—N5	120.4 (9)
C9—C8—H8	117.5	C26—C27—H27	119.8
C10—C9—C8	119.3 (7)	N5—C27—H27	119.8
C10—C9—H9	120.4

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₄H₈N₂O₄)(C₅H₅N)₆]·2C₅H₅N
M_r	1018.44
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	298
a, c (Å)	27.040 (2), 14.3178 (18)
V (Å³)	10468.6 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.34 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.779, 0.861
No. of measured, independent and observed [I > 2σ(I)] reflections	21466, 4609, 2743
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.152, 1.02
No. of reflections	4609
No. of parameters	316
No. of restraints	102
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.43

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

Selected bond lengths (Å) top

Ni1—N1	1.955 (3)	Ni1—N4	2.083 (3)
Ni1—O2	1.989 (3)	Ni1—N2	2.196 (4)
Ni1—O1ⁱ	2.060 (3)	Ni1—N3	2.201 (3)