Tris(5,6-dimethyl-1H-benzimidazole-κN3)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)nickel(II)

Li, Y.-H.; Li, F.-F.; Liu, X.-H.; Zhao, L.-Y.

doi:10.1107/S1600536812019502

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m739

doi:10.1107/S1600536812019502

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Tris(5,6-dimethyl-1H-benzimidazole-κN³)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)nickel(II)

Yue-Hua Li,^a ^* Feng-Feng Li,^b Xin-Hua Liu ^b and Ling-Yan Zhao ^c

^aCollege of Chemical Engineering, Hebei United University, Tangshan 063009, People's Republic of China, ^bCollege of Light Industry, Hebei United University, Tangshan 063009, People's Republic of China, and ^cQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: tsdgying@126.com

(Received 21 April 2012; accepted 1 May 2012; online 5 May 2012)

The title mononuclear complex, [Ni(C₇H₃NO₄)(C₉H₁₀N₂)₃], shows a central Ni^II atom which is coordinated by two carboxylate O atoms and the N atom from a pyridine-2,6-dicarboxylate ligand and by three N atoms from different 5,6-dimethyl-1H-benzimidazole ligands in a distorted octahedral geometry. The crystal structure shows intermolecular N—H⋯O hydrogen bonds.

Related literature

For related structures of dipicolinate complexes, see: How et al. (1991 ); Dong et al. (2010 ); Liu et al. (2011 ).

Experimental

Crystal data

[Ni(C₇H₃NO₄)(C₉H₁₀N₂)₃]
M_r = 662.38
Triclinic, $[P \overline 1]$
a = 7.5884 (7) Å
b = 9.4499 (9) Å
c = 23.839 (2) Å
α = 89.0040 (9)°
β = 81.484 (1)°
γ = 74.078 (1)°
V = 1625.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 293 K
0.18 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.872, T_max = 0.935
12396 measured reflections
5721 independent reflections
5078 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 0.94
5721 reflections
421 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4ⁱ	0.86	2.27	2.877 (2)	127
N5—H5A⋯O1ⁱⁱ	0.86	2.14	2.786 (2)	132
N7—H7A⋯O4ⁱⁱⁱ	0.86	1.94	2.788 (2)	171
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) x+1, y-1, z.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019502/im2371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019502/im2371Isup2.hkl

checkCIF report

Comment top

Benzimidazole and its derivatives are widely used as intermediates in synthesis and commonly coordinate to transition metals by N atom. Some Cu(II) dipicolinate complexes with additional imidazole ligands have been reported (How et al., 1991; Dong et al., 2010; Liu et al., 2011). Here, we report the crystal structure of the title compound.

The asymmetric unit of (I) contains one nickel(II), one 2,6- pyridinedicarboxylato and three 5,6-dimethylbenzimidazole ligands. The nickel center is six-coordinated in a distorted octahedral coordination geometry (Fig.1). Each nickel(II) is coordinated by one tridentate dipicolinato ligand via its carboxylate oxygen atoms and the pyridine nitrogen atom as donors (Ni1—N1= 1.997 (2); Ni1—O2=2.134 (1); Ni1—O3= 2.190 (1) Å). Three additional N donor atoms from three 5,6-dimethylbenzimidazole ligands complete the coordination sphere of nickel (Ni1- N from 2.056 (2) to 2.123 (2) Å). It is noteworthy that there exist strong N—H···O hydrogen bond interactions (Table 1) involving the carboxy group oxygen atoms of dipicolinato ligands as well as the NH functions of the benzimidazole ligands.

Related literature top

For related structures of dipicolinate complexes, see: How et al. (1991); Dong et al. (2010); Liu et al. (2011).

Experimental top

A mixture of Ni(NO₃)₂.6H₂O (290.8 mg, 0.5 mmol), 2,6-pyridinedicarboxylic acid (167 mg, 1 mmol), NaOH (80 mg, 2 mm mol), 5,6-dimethylbenzimidazole (73 mg, 0.5 mmol) and water (12 ml) was sealed in a 25 ml teflon-lined stainless steel reactor and heated to 413 K for 72 h. The reaction was cooled to room temperature over a period of 24 h. Green prismatic crystals of (I) suitable for X– ray difraction analysis were obtained with a yield of 38% (based Ni(NO₃)₂.6H₂O).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

Tris(5,6-dimethyl-1H-benzimidazole-κN³)(pyridine-2,6- dicarboxylato-κ³O²,N,O⁶)nickel(II) top

Crystal data top

[Ni(C₇H₃NO₄)(C₉H₁₀N₂)₃]	V = 1625.3 (3) Å³
M_r = 662.38	Z = 2
Triclinic, P1	F(000) = 692
Hall symbol: -P 1	D_x = 1.353 Mg m⁻³
a = 7.5884 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4499 (9) Å	µ = 0.65 mm⁻¹
c = 23.839 (2) Å	T = 293 K
α = 89.0040 (9)°	Block, green
β = 81.484 (1)°	0.18 × 0.15 × 0.14 mm
γ = 74.078 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5721 independent reflections
Radiation source: fine-focus sealed tube	5078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.872, T_max = 0.935	k = −11→11
12396 measured reflections	l = −28→28

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0503P)² + 0.7157P] where P = (F_o² + 2F_c²)/3
5721 reflections	(Δ/σ)_max = 0.001
421 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(C₇H₃NO₄)(C₉H₁₀N₂)₃]	γ = 74.078 (1)°
M_r = 662.38	V = 1625.3 (3) Å³
Triclinic, P1	Z = 2
a = 7.5884 (7) Å	Mo Kα radiation
b = 9.4499 (9) Å	µ = 0.65 mm⁻¹
c = 23.839 (2) Å	T = 293 K
α = 89.0040 (9)°	0.18 × 0.15 × 0.14 mm
β = 81.484 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5721 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5078 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.935	R_int = 0.021
12396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 0.94	Δρ_max = 0.27 e Å⁻³
5721 reflections	Δρ_min = −0.34 e Å⁻³
421 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	0.99661 (3)	0.63280 (2)	0.222282 (9)	0.02907 (9)
N1	0.9467 (2)	0.84068 (16)	0.19677 (6)	0.0297 (3)
N4	0.8878 (2)	0.57135 (18)	0.15400 (7)	0.0365 (4)
N2	1.1152 (2)	0.68619 (17)	0.29151 (7)	0.0342 (4)
N6	1.0510 (2)	0.41948 (17)	0.24934 (7)	0.0362 (4)
O3	0.71968 (17)	0.73993 (13)	0.26733 (6)	0.0349 (3)
O2	1.24640 (17)	0.62840 (15)	0.16685 (6)	0.0389 (3)
O4	0.51849 (18)	0.96040 (15)	0.28495 (7)	0.0459 (4)
C23	0.9603 (3)	0.1205 (2)	0.33262 (9)	0.0443 (5)
H23	1.0312	0.0285	0.3419	0.053*
C7	0.6658 (2)	0.87699 (19)	0.26080 (8)	0.0313 (4)
C6	0.7936 (2)	0.9412 (2)	0.21938 (8)	0.0318 (4)
C25	1.2158 (3)	0.3253 (2)	0.24373 (9)	0.0423 (5)
H25	1.3208	0.3441	0.2232	0.051*
C9	1.0555 (3)	0.6914 (2)	0.35000 (8)	0.0334 (4)
C1	1.0729 (3)	0.8747 (2)	0.15801 (8)	0.0351 (4)
O1	1.3415 (2)	0.7556 (2)	0.09431 (7)	0.0637 (5)
N7	1.2178 (2)	0.19856 (18)	0.27062 (8)	0.0453 (4)
H7A	1.3124	0.1237	0.2712	0.054*
C17	0.9343 (3)	0.3497 (2)	0.28265 (8)	0.0337 (4)
N3	1.3074 (2)	0.7679 (2)	0.33549 (7)	0.0439 (4)
H3A	1.4004	0.7997	0.3400	0.053*
C8	1.2639 (3)	0.7329 (2)	0.28601 (9)	0.0392 (5)
H8	1.3330	0.7411	0.2511	0.047*
C2	1.2345 (3)	0.7425 (2)	0.13747 (8)	0.0393 (5)
C27	0.9756 (3)	0.4677 (2)	0.11018 (8)	0.0343 (4)
C18	0.7458 (3)	0.3971 (2)	0.30265 (8)	0.0370 (4)
H18	0.6745	0.4876	0.2922	0.044*
C28	1.1593 (3)	0.3843 (2)	0.09756 (8)	0.0389 (4)
H28	1.2472	0.3954	0.1192	0.047*
C24	1.0398 (3)	0.2113 (2)	0.29699 (8)	0.0385 (5)
C16	0.9040 (3)	0.6554 (2)	0.38086 (9)	0.0408 (5)
H16	0.8247	0.6195	0.3625	0.049*
C19	0.6656 (3)	0.3076 (2)	0.33837 (9)	0.0392 (5)
C34	0.8467 (3)	0.4538 (2)	0.07628 (9)	0.0400 (5)
C10	1.1749 (3)	0.7435 (2)	0.37780 (9)	0.0389 (4)
N5	0.6813 (2)	0.5511 (2)	0.10001 (8)	0.0508 (5)
H5A	0.5765	0.5671	0.0879	0.061*
C22	0.7744 (3)	0.1691 (2)	0.35405 (9)	0.0426 (5)
C29	1.2092 (3)	0.2845 (2)	0.05225 (9)	0.0441 (5)
C5	0.7630 (3)	1.0872 (2)	0.20455 (10)	0.0462 (5)
H5	0.6570	1.1581	0.2207	0.055*
C3	1.0500 (3)	1.0176 (3)	0.14083 (10)	0.0513 (6)
H3	1.1374	1.0417	0.1135	0.062*
C26	0.7146 (3)	0.6156 (2)	0.14517 (9)	0.0457 (5)
H26	0.6236	0.6855	0.1682	0.055*
C14	0.7053 (4)	0.6362 (4)	0.47250 (12)	0.0769 (8)
H14A	0.6200	0.7242	0.4900	0.115*
H14B	0.7447	0.5672	0.5013	0.115*
H14C	0.6455	0.5934	0.4473	0.115*
C32	1.0753 (4)	0.2693 (2)	0.01906 (9)	0.0498 (6)
C33	0.8945 (3)	0.3547 (3)	0.03046 (9)	0.0502 (5)
H33	0.8070	0.3464	0.0082	0.060*
C15	0.8732 (3)	0.6738 (3)	0.43916 (9)	0.0496 (5)
C11	1.1441 (3)	0.7635 (3)	0.43657 (9)	0.0519 (6)
H11	1.2237	0.7997	0.4548	0.062*
C31	1.1298 (5)	0.1571 (3)	−0.02934 (11)	0.0750 (8)
H31A	1.0250	0.1635	−0.0484	0.112*
H31B	1.1704	0.0601	−0.0147	0.112*
H31C	1.2287	0.1765	−0.0556	0.112*
C12	0.9932 (4)	0.7287 (3)	0.46718 (9)	0.0554 (6)
C4	0.8950 (4)	1.1245 (3)	0.16495 (11)	0.0579 (6)
H4	0.8790	1.2220	0.1546	0.069*
C20	0.4618 (3)	0.3609 (3)	0.36204 (11)	0.0574 (6)
H20A	0.4480	0.3879	0.4014	0.086*
H20B	0.4040	0.2837	0.3582	0.086*
H20C	0.4039	0.4449	0.3415	0.086*
C13	0.9562 (5)	0.7524 (4)	0.53117 (11)	0.0908 (10)
H13A	1.0543	0.7846	0.5433	0.136*
H13B	0.9503	0.6616	0.5491	0.136*
H13C	0.8405	0.8258	0.5416	0.136*
C21	0.6875 (4)	0.0748 (3)	0.39503 (11)	0.0608 (7)
H21A	0.7793	−0.0147	0.4009	0.091*
H21B	0.5884	0.0518	0.3796	0.091*
H21C	0.6395	0.1274	0.4306	0.091*
C30	1.4084 (4)	0.1915 (3)	0.03947 (11)	0.0643 (7)
H30A	1.4795	0.2179	0.0656	0.096*
H30B	1.4592	0.2084	0.0014	0.096*
H30C	1.4128	0.0894	0.0432	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02265 (13)	0.02596 (14)	0.03356 (14)	−0.00152 (9)	0.00148 (9)	0.00487 (9)
N1	0.0260 (8)	0.0300 (8)	0.0320 (8)	−0.0065 (6)	−0.0031 (6)	0.0069 (6)
N4	0.0296 (8)	0.0356 (9)	0.0405 (9)	−0.0043 (7)	−0.0027 (7)	0.0024 (7)
N2	0.0307 (8)	0.0341 (8)	0.0354 (9)	−0.0071 (7)	−0.0015 (7)	0.0052 (7)
N6	0.0329 (9)	0.0284 (8)	0.0421 (9)	−0.0010 (7)	−0.0037 (7)	0.0052 (7)
O3	0.0266 (6)	0.0282 (7)	0.0438 (8)	−0.0027 (5)	0.0035 (5)	0.0076 (6)
O2	0.0274 (7)	0.0441 (8)	0.0395 (8)	−0.0039 (6)	0.0022 (6)	0.0033 (6)
O4	0.0290 (7)	0.0337 (8)	0.0642 (10)	0.0022 (6)	0.0063 (7)	0.0032 (7)
C23	0.0577 (14)	0.0256 (10)	0.0444 (12)	−0.0020 (9)	−0.0101 (10)	0.0061 (9)
C7	0.0239 (9)	0.0286 (10)	0.0383 (10)	−0.0027 (7)	−0.0034 (8)	0.0021 (8)
C6	0.0295 (9)	0.0275 (9)	0.0364 (10)	−0.0046 (7)	−0.0052 (8)	0.0052 (8)
C25	0.0344 (11)	0.0362 (11)	0.0489 (12)	−0.0003 (9)	−0.0014 (9)	0.0053 (9)
C9	0.0337 (10)	0.0284 (9)	0.0345 (10)	−0.0037 (8)	−0.0036 (8)	0.0041 (8)
C1	0.0314 (10)	0.0448 (11)	0.0312 (10)	−0.0152 (8)	−0.0038 (8)	0.0096 (8)
O1	0.0379 (8)	0.0897 (13)	0.0485 (9)	−0.0043 (8)	0.0132 (7)	0.0230 (9)
N7	0.0388 (10)	0.0315 (9)	0.0539 (11)	0.0081 (7)	−0.0040 (8)	0.0064 (8)
C17	0.0397 (10)	0.0241 (9)	0.0354 (10)	−0.0049 (8)	−0.0071 (8)	0.0027 (8)
N3	0.0341 (9)	0.0525 (11)	0.0479 (10)	−0.0169 (8)	−0.0058 (8)	0.0023 (8)
C8	0.0336 (10)	0.0428 (11)	0.0391 (11)	−0.0106 (9)	0.0006 (8)	0.0053 (9)
C2	0.0257 (10)	0.0573 (13)	0.0335 (10)	−0.0108 (9)	−0.0011 (8)	0.0072 (9)
C27	0.0384 (10)	0.0300 (10)	0.0337 (10)	−0.0101 (8)	−0.0026 (8)	0.0073 (8)
C18	0.0364 (10)	0.0260 (9)	0.0441 (11)	−0.0006 (8)	−0.0071 (9)	0.0038 (8)
C28	0.0390 (11)	0.0367 (11)	0.0387 (11)	−0.0091 (9)	−0.0010 (9)	0.0034 (8)
C24	0.0424 (11)	0.0283 (10)	0.0394 (11)	0.0003 (8)	−0.0082 (9)	0.0006 (8)
C16	0.0403 (11)	0.0423 (11)	0.0398 (11)	−0.0138 (9)	−0.0016 (9)	0.0052 (9)
C19	0.0439 (11)	0.0338 (10)	0.0394 (11)	−0.0105 (9)	−0.0047 (9)	0.0006 (8)
C34	0.0427 (11)	0.0402 (11)	0.0395 (11)	−0.0150 (9)	−0.0081 (9)	0.0096 (9)
C10	0.0370 (11)	0.0362 (11)	0.0415 (11)	−0.0070 (8)	−0.0059 (9)	0.0045 (9)
N5	0.0359 (10)	0.0623 (12)	0.0540 (11)	−0.0091 (9)	−0.0143 (8)	0.0018 (9)
C22	0.0581 (14)	0.0325 (11)	0.0369 (11)	−0.0130 (10)	−0.0055 (10)	0.0033 (9)
C29	0.0530 (13)	0.0370 (11)	0.0373 (11)	−0.0109 (10)	0.0059 (9)	0.0028 (9)
C5	0.0465 (12)	0.0288 (10)	0.0581 (14)	−0.0048 (9)	−0.0032 (10)	0.0081 (9)
C3	0.0533 (14)	0.0510 (13)	0.0524 (13)	−0.0238 (11)	−0.0008 (11)	0.0204 (11)
C26	0.0324 (11)	0.0499 (13)	0.0494 (13)	−0.0031 (9)	−0.0041 (9)	−0.0001 (10)
C14	0.0722 (19)	0.104 (2)	0.0523 (15)	−0.0346 (17)	0.0154 (13)	0.0067 (15)
C32	0.0753 (16)	0.0429 (12)	0.0329 (11)	−0.0229 (12)	−0.0008 (11)	0.0032 (9)
C33	0.0646 (15)	0.0521 (13)	0.0414 (12)	−0.0255 (12)	−0.0141 (11)	0.0078 (10)
C15	0.0527 (13)	0.0550 (14)	0.0378 (11)	−0.0146 (11)	0.0026 (10)	0.0069 (10)
C11	0.0561 (14)	0.0587 (14)	0.0437 (12)	−0.0166 (11)	−0.0150 (11)	−0.0005 (10)
C31	0.105 (2)	0.0683 (18)	0.0490 (15)	−0.0240 (17)	−0.0016 (15)	−0.0136 (13)
C12	0.0630 (15)	0.0625 (15)	0.0365 (12)	−0.0121 (12)	−0.0042 (11)	0.0030 (11)
C4	0.0665 (16)	0.0356 (12)	0.0719 (16)	−0.0181 (11)	−0.0056 (13)	0.0220 (11)
C20	0.0497 (14)	0.0542 (14)	0.0639 (15)	−0.0128 (11)	0.0020 (11)	0.0094 (12)
C13	0.107 (3)	0.128 (3)	0.0393 (15)	−0.039 (2)	−0.0024 (15)	−0.0056 (16)
C21	0.0778 (18)	0.0452 (14)	0.0577 (15)	−0.0200 (12)	−0.0007 (13)	0.0167 (11)
C30	0.0601 (15)	0.0596 (16)	0.0592 (15)	−0.0043 (12)	0.0143 (12)	−0.0126 (12)

Geometric parameters (Å, º) top

Ni1—N1	1.9976 (15)	C16—H16	0.9300
Ni1—N6	2.0561 (15)	C19—C22	1.420 (3)
Ni1—N4	2.0886 (16)	C19—C20	1.513 (3)
Ni1—N2	2.1227 (16)	C34—C33	1.390 (3)
Ni1—O2	2.1348 (13)	C34—N5	1.384 (3)
Ni1—O3	2.1901 (12)	C10—C11	1.393 (3)
N1—C6	1.330 (2)	N5—C26	1.335 (3)
N1—C1	1.331 (2)	N5—H5A	0.8600
N4—C26	1.313 (3)	C22—C21	1.511 (3)
N4—C27	1.402 (2)	C29—C32	1.414 (3)
N2—C8	1.309 (3)	C29—C30	1.515 (3)
N2—C9	1.398 (2)	C5—C4	1.386 (3)
N6—C25	1.310 (2)	C5—H5	0.9300
N6—C17	1.394 (2)	C3—C4	1.379 (3)
O3—C7	1.261 (2)	C3—H3	0.9300
O2—C2	1.265 (2)	C26—H26	0.9300
O4—C7	1.243 (2)	C14—C15	1.523 (3)
C23—C22	1.379 (3)	C14—H14A	0.9600
C23—C24	1.389 (3)	C14—H14B	0.9600
C23—H23	0.9300	C14—H14C	0.9600
C7—C6	1.517 (3)	C32—C33	1.378 (3)
C6—C5	1.384 (3)	C32—C31	1.512 (3)
C25—N7	1.346 (3)	C33—H33	0.9300
C25—H25	0.9300	C15—C12	1.413 (3)
C9—C10	1.391 (3)	C11—C12	1.379 (3)
C9—C16	1.391 (3)	C11—H11	0.9300
C1—C3	1.377 (3)	C31—H31A	0.9600
C1—C2	1.518 (3)	C31—H31B	0.9600
O1—C2	1.239 (2)	C31—H31C	0.9600
N7—C24	1.377 (3)	C12—C13	1.519 (3)
N7—H7A	0.8600	C4—H4	0.9300
C17—C18	1.389 (3)	C20—H20A	0.9600
C17—C24	1.400 (3)	C20—H20B	0.9600
N3—C8	1.341 (3)	C20—H20C	0.9600
N3—C10	1.379 (3)	C13—H13A	0.9600
N3—H3A	0.8600	C13—H13B	0.9600
C8—H8	0.9300	C13—H13C	0.9600
C27—C28	1.391 (3)	C21—H21A	0.9600
C27—C34	1.391 (3)	C21—H21B	0.9600
C18—C19	1.384 (3)	C21—H21C	0.9600
C18—H18	0.9300	C30—H30A	0.9600
C28—C29	1.385 (3)	C30—H30B	0.9600
C28—H28	0.9300	C30—H30C	0.9600
C16—C15	1.381 (3)

N1—Ni1—N6	179.06 (6)	C22—C19—C20	120.27 (19)
N1—Ni1—N4	91.46 (6)	C33—C34—N5	133.1 (2)
N6—Ni1—N4	89.43 (6)	C33—C34—C27	121.8 (2)
N1—Ni1—N2	90.59 (6)	N5—C34—C27	105.10 (18)
N6—Ni1—N2	88.51 (6)	N3—C10—C9	105.30 (17)
N4—Ni1—N2	177.57 (6)	N3—C10—C11	133.4 (2)
N1—Ni1—O2	77.98 (6)	C9—C10—C11	121.2 (2)
N6—Ni1—O2	101.73 (6)	C26—N5—C34	107.34 (17)
N4—Ni1—O2	89.53 (6)	C26—N5—H5A	126.3
N2—Ni1—O2	89.62 (6)	C34—N5—H5A	126.3
N1—Ni1—O3	76.12 (5)	C23—C22—C19	120.33 (19)
N6—Ni1—O3	104.15 (6)	C23—C22—C21	119.6 (2)
N4—Ni1—O3	92.00 (6)	C19—C22—C21	120.1 (2)
N2—Ni1—O3	89.76 (6)	C28—C29—C32	120.3 (2)
O2—Ni1—O3	154.09 (5)	C28—C29—C30	118.8 (2)
C6—N1—C1	121.90 (16)	C32—C29—C30	120.9 (2)
C6—N1—Ni1	120.19 (12)	C6—C5—C4	118.0 (2)
C1—N1—Ni1	117.88 (13)	C6—C5—H5	121.0
C26—N4—C27	104.39 (17)	C4—C5—H5	121.0
C26—N4—Ni1	126.53 (14)	C1—C3—C4	118.7 (2)
C27—N4—Ni1	128.93 (13)	C1—C3—H3	120.7
C8—N2—C9	104.53 (16)	C4—C3—H3	120.7
C8—N2—Ni1	124.08 (14)	N4—C26—N5	113.77 (19)
C9—N2—Ni1	131.26 (13)	N4—C26—H26	123.1
C25—N6—C17	105.31 (16)	N5—C26—H26	123.1
C25—N6—Ni1	124.83 (14)	C15—C14—H14A	109.5
C17—N6—Ni1	129.39 (12)	C15—C14—H14B	109.5
C7—O3—Ni1	114.55 (11)	H14A—C14—H14B	109.5
C2—O2—Ni1	113.29 (12)	C15—C14—H14C	109.5
C22—C23—C24	118.82 (18)	H14A—C14—H14C	109.5
C22—C23—H23	120.6	H14B—C14—H14C	109.5
C24—C23—H23	120.6	C33—C32—C29	120.9 (2)
O4—C7—O3	125.25 (17)	C33—C32—C31	119.2 (2)
O4—C7—C6	118.94 (16)	C29—C32—C31	119.9 (2)
O3—C7—C6	115.81 (15)	C32—C33—C34	118.1 (2)
N1—C6—C5	120.68 (18)	C32—C33—H33	121.0
N1—C6—C7	112.95 (15)	C34—C33—H33	121.0
C5—C6—C7	126.36 (17)	C16—C15—C12	120.6 (2)
N6—C25—N7	113.26 (19)	C16—C15—C14	118.6 (2)
N6—C25—H25	123.4	C12—C15—C14	120.7 (2)
N7—C25—H25	123.4	C12—C11—C10	118.6 (2)
C10—C9—C16	120.18 (18)	C12—C11—H11	120.7
C10—C9—N2	109.36 (17)	C10—C11—H11	120.7
C16—C9—N2	130.46 (18)	C32—C31—H31A	109.5
N1—C1—C3	120.40 (19)	C32—C31—H31B	109.5
N1—C1—C2	112.89 (16)	H31A—C31—H31B	109.5
C3—C1—C2	126.71 (18)	C32—C31—H31C	109.5
C25—N7—C24	107.06 (16)	H31A—C31—H31C	109.5
C25—N7—H7A	126.5	H31B—C31—H31C	109.5
C24—N7—H7A	126.5	C11—C12—C15	120.3 (2)
C18—C17—N6	131.03 (17)	C11—C12—C13	119.2 (2)
C18—C17—C24	120.27 (18)	C15—C12—C13	120.5 (2)
N6—C17—C24	108.68 (17)	C3—C4—C5	120.3 (2)
C8—N3—C10	107.15 (17)	C3—C4—H4	119.8
C8—N3—H3A	126.4	C5—C4—H4	119.8
C10—N3—H3A	126.4	C19—C20—H20A	109.5
N2—C8—N3	113.66 (18)	C19—C20—H20B	109.5
N2—C8—H8	123.2	H20A—C20—H20B	109.5
N3—C8—H8	123.2	C19—C20—H20C	109.5
O1—C2—O2	126.2 (2)	H20A—C20—H20C	109.5
O1—C2—C1	118.03 (19)	H20B—C20—H20C	109.5
O2—C2—C1	115.77 (16)	C12—C13—H13A	109.5
C28—C27—C34	119.94 (18)	C12—C13—H13B	109.5
C28—C27—N4	130.66 (18)	H13A—C13—H13B	109.5
C34—C27—N4	109.40 (17)	C12—C13—H13C	109.5
C19—C18—C17	119.02 (17)	H13A—C13—H13C	109.5
C19—C18—H18	120.5	H13B—C13—H13C	109.5
C17—C18—H18	120.5	C22—C21—H21A	109.5
C29—C28—C27	119.0 (2)	C22—C21—H21B	109.5
C29—C28—H28	120.5	H21A—C21—H21B	109.5
C27—C28—H28	120.5	C22—C21—H21C	109.5
N7—C24—C23	133.22 (18)	H21A—C21—H21C	109.5
N7—C24—C17	105.66 (17)	H21B—C21—H21C	109.5
C23—C24—C17	121.09 (19)	C29—C30—H30A	109.5
C15—C16—C9	119.0 (2)	C29—C30—H30B	109.5
C15—C16—H16	120.5	H30A—C30—H30B	109.5
C9—C16—H16	120.5	C29—C30—H30C	109.5
C18—C19—C22	120.42 (19)	H30A—C30—H30C	109.5
C18—C19—C20	119.28 (18)	H30B—C30—H30C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4ⁱ	0.86	2.27	2.877 (2)	127
N5—H5A···O1ⁱⁱ	0.86	2.14	2.786 (2)	132
N7—H7A···O4ⁱⁱⁱ	0.86	1.94	2.788 (2)	171

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

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₃NO₄)(C₉H₁₀N₂)₃]
M_r	662.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5884 (7), 9.4499 (9), 23.839 (2)
α, β, γ (°)	89.0040 (9), 81.484 (1), 74.078 (1)
V (Å³)	1625.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.18 × 0.15 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.872, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	12396, 5721, 5078
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 0.94
No. of reflections	5721
No. of parameters	421
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4ⁱ	0.86	2.27	2.877 (2)	127
N5—H5A···O1ⁱⁱ	0.86	2.14	2.786 (2)	132
N7—H7A···O4ⁱⁱⁱ	0.86	1.94	2.788 (2)	171

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

Acknowledgements

The authors thank Hebei United University for supporting this work.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dong, G.-Y., Fan, L.-H., Yang, L.-X. & Khan, I. U. (2010). Acta Cryst. E66, m532. Web of Science CSD CrossRef IUCr Journals Google Scholar
How, G. A., Whei, L. K., Graeme, R. H., Jeffrey, A. C., Mary, M. & Nick, C. (1991). J. Chem. Soc. Dalton Trans. pp. 3193–3291. Google Scholar
Liu, T. F., Wu, W. F., Wan, C. Q., He, C. H., Jiao, C. H. & Cui, G. H. (2011). J. Coord. Chem. 64, 975–986. Web of Science CSD CrossRef CAS 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

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