Bis(formato-κO)bis­[1-(pyridin-2-yl)ethanone oxime-κ2N,N′]nickel(II)

Li, L.; Qiu, X.; Li, D.

doi:10.1107/S1600536811050859

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m2

doi:10.1107/S1600536811050859

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Bis(formato-κO)bis[1-(pyridin-2-yl)ethanone oxime-κ²N,N′]nickel(II)

Leilei Li,^a Xiumin Qiu ^a and Dacheng Li ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@163.com

(Received 18 November 2011; accepted 26 November 2011; online 3 December 2011)

In the title compound, [Ni(HCOO)₂(C₇H₈N₂O)₂], the Ni atom is six-coordinated by four N atoms from two oxime ligands and by two O atoms from two formate ions in a distorted octahedral geometry, with the oxime-N atoms mutually trans. The molecular conformation is stabilized by intramolecular O—H⋯O hydrogen bonds.

Related literature

For uses of oximes, see: Davidson et al. (2007 ); Pavlishchuk et al. (2003 ) and of 2-pyridyl oximes, see: Chaudhuri (2003 ); Milios et al. (2006 ). For a related structure, see: Zuo et al. (2007 ).

Experimental

Crystal data

[Ni(CHO₂)₂(C₇H₈N₂O)₂]
M_r = 421.05
Monoclinic,
a = 10.5000 (12) Å
b = 14.6109 (16) Å
c = 15.7391 (17) Å
β = 131.850 (2)°
V = 1798.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.807, T_max = 0.887
9294 measured reflections
3171 independent reflections
2209 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.137
S = 1.00
3171 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.69	2.508 (4)	177
O2—H2⋯O6	0.82	1.67	2.482 (4)	169

Data collection: SMART (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/S1600536811050859/vm2139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811050859/vm2139Isup2.hkl

checkCIF report

Comment top

Recently, there is a intense interest in the coordination chemistry of oximes (Davidson et al., 2007; Pavlishchuk et al., 2003). 2-Pyridyl oximes which are versatile ligands for a variety of research objectives are popular ligands in coordination chemistry (Chaudhuri, 2003; Milios et al., 2006). We report here the synthesis and structure of the title compound.

The complex (Fig. 1) crystallizes in monoclinic space group P2₁/c. The central Ni atom is six coordinated by four N atoms from the oxime ligands and two O atoms from the formate ions in a distorted octahedral geometry. The N1 and N3 atoms of methyl 2-pyridylketone oxime occupy the axial sites. The N2, N4 and O3, O5 are in the equatorial plane. The six coordinated molecule is the cis-cis-trans isomer considering the positions of the coordinated formyl groups, pyridyl and oxime nitrogen atoms, respectively (Zuo et al., 2007). The Ni–N bond distances in the compound are in the range of 2.075 (3)–2.107 (3) Å which is longer than the Ni–O distances (2.049 (3)–2.070 (3) Å). The molecular conformation is stabilized by intramolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For uses of oximes, see: Davidson et al. (2007); Pavlishchuk et al. (2003) and of 2-pyridyl oximes, see: Chaudhuri (2003); Milios et al. (2006). For a related structure, see: Zuo et al. (2007)

Experimental top

A solution of NiSO₄.6H₂O (0.131 g, 0.5 mmol) and methyl 2-pyridyl ketone oxime (0.068 g, 0.5 mmol) in MeOH was treated with equivalent amounts of HCOONa. After stirring for 6 h, a green solution was obtained. After filtration, green block crystals suitable for single-crystal X-ray diffraction were obtained after two weeks by evaporating the resulting filtrate in air. Yield: 47% (based on Ni).

Computing details top

Data collection: SMART (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. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.

Bis(formato-κO)bis[1-(pyridin-2-yl)ethanone oxime-κ²N,N']nickel(II) top

Crystal data top

[Ni(CHO₂)₂(C₇H₈N₂O)₂]	F(000) = 872
M_r = 421.05	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3030 reflections
a = 10.5000 (12) Å	θ = 2.4–25.3°
b = 14.6109 (16) Å	µ = 1.12 mm⁻¹
c = 15.7391 (17) Å	T = 298 K
β = 131.850 (2)°	Block, green
V = 1798.6 (3) Å³	0.20 × 0.17 × 0.11 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3171 independent reflections
Radiation source: fine-focus sealed tube	2209 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.807, T_max = 0.887	k = −16→17
9294 measured reflections	l = −14→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.077P)²] where P = (F_o² + 2F_c²)/3
3171 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ni(CHO₂)₂(C₇H₈N₂O)₂]	V = 1798.6 (3) Å³
M_r = 421.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5000 (12) Å	µ = 1.12 mm⁻¹
b = 14.6109 (16) Å	T = 298 K
c = 15.7391 (17) Å	0.20 × 0.17 × 0.11 mm
β = 131.850 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3171 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2209 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.887	R_int = 0.077
9294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.00	Δρ_max = 0.98 e Å⁻³
3171 reflections	Δρ_min = −0.38 e Å⁻³
244 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	0.79945 (5)	0.29154 (3)	0.43579 (3)	0.0370 (2)
N1	0.9617 (4)	0.2714 (2)	0.6114 (2)	0.0438 (8)
N2	0.9641 (4)	0.1861 (2)	0.4685 (2)	0.0417 (7)
N3	0.6356 (4)	0.2740 (2)	0.2604 (2)	0.0425 (7)
N4	0.6175 (3)	0.19950 (19)	0.4010 (2)	0.0389 (7)
O1	0.9530 (4)	0.3159 (2)	0.6839 (2)	0.0625 (8)
H1	0.8715	0.3512	0.6473	0.094*
O2	0.6505 (4)	0.3135 (2)	0.1895 (2)	0.0600 (8)
H2	0.7258	0.3525	0.2244	0.090*
O3	0.6415 (3)	0.39657 (19)	0.4059 (2)	0.0594 (7)
O4	0.6976 (4)	0.4197 (3)	0.5686 (3)	0.0824 (11)
O5	0.9714 (3)	0.38535 (19)	0.4670 (2)	0.0565 (7)
O6	0.9048 (4)	0.4151 (2)	0.3023 (2)	0.0647 (8)
C1	1.1889 (5)	0.1813 (3)	0.7810 (3)	0.0666 (13)
H1A	1.1802	0.2260	0.8217	0.100*
H1B	1.3051	0.1780	0.8133	0.100*
H1C	1.1540	0.1226	0.7866	0.100*
C2	1.0756 (4)	0.2085 (3)	0.6584 (3)	0.0453 (9)
C3	1.0842 (4)	0.1614 (3)	0.5792 (3)	0.0454 (9)
C4	1.2087 (5)	0.0964 (3)	0.6154 (4)	0.0640 (12)
H4	1.2920	0.0811	0.6921	0.077*
C5	1.2066 (6)	0.0551 (3)	0.5356 (4)	0.0763 (14)
H5	1.2880	0.0113	0.5578	0.092*
C6	1.0840 (6)	0.0793 (3)	0.4241 (4)	0.0692 (13)
H6	1.0803	0.0518	0.3692	0.083*
C7	0.9647 (5)	0.1451 (3)	0.3928 (3)	0.0527 (10)
H7	0.8819	0.1614	0.3164	0.063*
C8	0.3945 (5)	0.1940 (3)	0.0882 (3)	0.0625 (12)
H8A	0.3672	0.2490	0.0455	0.094*
H8B	0.2915	0.1674	0.0643	0.094*
H8C	0.4493	0.1514	0.0750	0.094*
C9	0.5122 (4)	0.2164 (2)	0.2125 (3)	0.0399 (8)
C10	0.4964 (4)	0.1737 (3)	0.2905 (3)	0.0398 (8)
C11	0.3649 (5)	0.1158 (3)	0.2541 (3)	0.0508 (10)
H11	0.2837	0.0982	0.1780	0.061*
C12	0.3560 (5)	0.0843 (3)	0.3330 (4)	0.0570 (11)
H12	0.2686	0.0449	0.3105	0.068*
C13	0.4765 (5)	0.1115 (3)	0.4443 (3)	0.0535 (10)
H13	0.4710	0.0921	0.4981	0.064*
C14	0.6058 (4)	0.1680 (3)	0.4749 (3)	0.0428 (9)
H14	0.6892	0.1852	0.5510	0.051*
C15	0.6164 (5)	0.4323 (3)	0.4662 (4)	0.0604 (11)
H15	0.5257	0.4733	0.4293	0.072*
C16	0.9880 (5)	0.4261 (3)	0.4058 (4)	0.0535 (10)
H16	1.0734	0.4703	0.4419	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0332 (3)	0.0470 (3)	0.0287 (3)	−0.0006 (2)	0.0199 (2)	−0.00075 (19)
N1	0.0397 (17)	0.061 (2)	0.0314 (16)	−0.0092 (15)	0.0238 (15)	−0.0067 (14)
N2	0.0377 (16)	0.0543 (19)	0.0363 (17)	0.0045 (13)	0.0260 (15)	0.0063 (13)
N3	0.0422 (17)	0.055 (2)	0.0331 (16)	0.0040 (15)	0.0263 (15)	0.0067 (14)
N4	0.0350 (16)	0.0485 (18)	0.0303 (15)	−0.0008 (13)	0.0206 (14)	−0.0040 (12)
O1	0.0598 (17)	0.091 (2)	0.0364 (15)	0.0007 (15)	0.0322 (14)	−0.0092 (14)
O2	0.0632 (18)	0.082 (2)	0.0373 (15)	−0.0115 (15)	0.0347 (14)	0.0029 (13)
O3	0.0552 (17)	0.0595 (18)	0.0588 (18)	0.0075 (13)	0.0361 (15)	−0.0041 (14)
O4	0.083 (2)	0.104 (3)	0.073 (2)	0.022 (2)	0.058 (2)	−0.0027 (19)
O5	0.0495 (16)	0.0650 (19)	0.0470 (16)	−0.0112 (13)	0.0289 (14)	0.0010 (13)
O6	0.0609 (18)	0.074 (2)	0.0571 (19)	−0.0065 (16)	0.0386 (16)	0.0083 (16)
C1	0.051 (3)	0.095 (3)	0.037 (2)	0.004 (2)	0.022 (2)	0.012 (2)
C2	0.0305 (19)	0.062 (3)	0.033 (2)	−0.0076 (18)	0.0172 (17)	0.0042 (17)
C3	0.035 (2)	0.055 (2)	0.044 (2)	0.0015 (17)	0.0258 (18)	0.0078 (18)
C4	0.052 (3)	0.077 (3)	0.058 (3)	0.014 (2)	0.034 (2)	0.020 (2)
C5	0.071 (3)	0.078 (3)	0.091 (4)	0.033 (3)	0.059 (3)	0.026 (3)
C6	0.080 (3)	0.074 (3)	0.083 (4)	0.012 (3)	0.066 (3)	0.000 (3)
C7	0.055 (2)	0.063 (3)	0.050 (2)	0.007 (2)	0.039 (2)	0.003 (2)
C8	0.056 (3)	0.087 (3)	0.032 (2)	−0.012 (2)	0.024 (2)	−0.012 (2)
C9	0.0332 (19)	0.052 (2)	0.0245 (17)	0.0053 (17)	0.0151 (16)	−0.0010 (15)
C10	0.0371 (19)	0.045 (2)	0.0356 (19)	0.0024 (16)	0.0237 (17)	−0.0014 (16)
C11	0.045 (2)	0.058 (3)	0.039 (2)	−0.0116 (18)	0.0237 (18)	−0.0149 (18)
C12	0.058 (3)	0.057 (3)	0.064 (3)	−0.019 (2)	0.044 (2)	−0.012 (2)
C13	0.062 (3)	0.057 (3)	0.049 (2)	−0.011 (2)	0.040 (2)	−0.0053 (19)
C14	0.042 (2)	0.054 (2)	0.0329 (19)	−0.0052 (17)	0.0250 (18)	−0.0043 (17)
C15	0.052 (3)	0.057 (3)	0.077 (3)	−0.002 (2)	0.045 (3)	−0.011 (2)
C16	0.042 (2)	0.050 (2)	0.062 (3)	0.0012 (18)	0.032 (2)	0.008 (2)

Geometric parameters (Å, º) top

Ni1—O5	2.049 (3)	C2—C3	1.478 (5)
Ni1—O3	2.070 (3)	C3—C4	1.394 (5)
Ni1—N3	2.075 (3)	C4—C5	1.379 (7)
Ni1—N1	2.085 (3)	C4—H4	0.9300
Ni1—N4	2.089 (3)	C5—C6	1.359 (6)
Ni1—N2	2.107 (3)	C5—H5	0.9300
N1—C2	1.281 (5)	C6—C7	1.382 (5)
N1—O1	1.368 (4)	C6—H6	0.9300
N2—C7	1.337 (5)	C7—H7	0.9300
N2—C3	1.351 (4)	C8—C9	1.494 (5)
N3—C9	1.285 (4)	C8—H8A	0.9600
N3—O2	1.356 (4)	C8—H8B	0.9600
N4—C14	1.330 (4)	C8—H8C	0.9600
N4—C10	1.354 (4)	C9—C10	1.481 (5)
O1—H1	0.8200	C10—C11	1.377 (5)
O2—H2	0.8200	C11—C12	1.386 (5)
O3—C15	1.256 (5)	C11—H11	0.9300
O4—C15	1.235 (5)	C12—C13	1.367 (5)
O5—C16	1.239 (5)	C12—H12	0.9300
O6—C16	1.243 (5)	C13—C14	1.373 (5)
C1—C2	1.493 (5)	C13—H13	0.9300
C1—H1A	0.9600	C14—H14	0.9300
C1—H1B	0.9600	C15—H15	0.9300
C1—H1C	0.9600	C16—H16	0.9300

O5—Ni1—O3	90.17 (12)	C5—C4—C3	119.0 (4)
O5—Ni1—N3	102.57 (11)	C5—C4—H4	120.5
O3—Ni1—N3	87.81 (11)	C3—C4—H4	120.5
O5—Ni1—N1	88.09 (11)	C6—C5—C4	119.2 (4)
O3—Ni1—N1	103.18 (12)	C6—C5—H5	120.4
N3—Ni1—N1	164.78 (12)	C4—C5—H5	120.4
O5—Ni1—N4	177.98 (11)	C5—C6—C7	119.5 (4)
O3—Ni1—N4	87.92 (11)	C5—C6—H6	120.2
N3—Ni1—N4	76.72 (11)	C7—C6—H6	120.2
N1—Ni1—N4	92.98 (11)	N2—C7—C6	122.4 (4)
O5—Ni1—N2	88.99 (12)	N2—C7—H7	118.8
O3—Ni1—N2	178.97 (12)	C6—C7—H7	118.8
N3—Ni1—N2	92.95 (11)	C9—C8—H8A	109.5
N1—Ni1—N2	76.20 (11)	C9—C8—H8B	109.5
N4—Ni1—N2	92.93 (12)	H8A—C8—H8B	109.5
C2—N1—O1	114.6 (3)	C9—C8—H8C	109.5
C2—N1—Ni1	119.3 (3)	H8A—C8—H8C	109.5
O1—N1—Ni1	126.0 (2)	H8B—C8—H8C	109.5
C7—N2—C3	118.3 (3)	N3—C9—C10	114.5 (3)
C7—N2—Ni1	126.9 (3)	N3—C9—C8	122.8 (3)
C3—N2—Ni1	114.7 (2)	C10—C9—C8	122.7 (3)
C9—N3—O2	114.8 (3)	N4—C10—C11	121.8 (3)
C9—N3—Ni1	118.6 (2)	N4—C10—C9	114.8 (3)
O2—N3—Ni1	126.4 (2)	C11—C10—C9	123.3 (3)
C14—N4—C10	118.2 (3)	C10—C11—C12	118.7 (3)
C14—N4—Ni1	126.6 (2)	C10—C11—H11	120.6
C10—N4—Ni1	115.2 (2)	C12—C11—H11	120.6
N1—O1—H1	109.5	C13—C12—C11	119.6 (4)
N3—O2—H2	109.5	C13—C12—H12	120.2
C15—O3—Ni1	132.6 (3)	C11—C12—H12	120.2
C16—O5—Ni1	133.9 (3)	C12—C13—C14	118.6 (4)
C2—C1—H1A	109.5	C12—C13—H13	120.7
C2—C1—H1B	109.5	C14—C13—H13	120.7
H1A—C1—H1B	109.5	N4—C14—C13	123.2 (3)
C2—C1—H1C	109.5	N4—C14—H14	118.4
H1A—C1—H1C	109.5	C13—C14—H14	118.4
H1B—C1—H1C	109.5	O4—C15—O3	127.8 (4)
N1—C2—C3	113.9 (3)	O4—C15—H15	116.1
N1—C2—C1	124.6 (4)	O3—C15—H15	116.1
C3—C2—C1	121.4 (4)	O5—C16—O6	128.1 (4)
N2—C3—C4	121.5 (4)	O5—C16—H16	115.9
N2—C3—C2	115.8 (3)	O6—C16—H16	115.9
C4—C3—C2	122.7 (4)

O5—Ni1—N1—C2	−91.6 (3)	O3—Ni1—O5—C16	−87.8 (4)
O3—Ni1—N1—C2	178.7 (3)	N3—Ni1—O5—C16	0.0 (4)
N3—Ni1—N1—C2	43.4 (6)	N1—Ni1—O5—C16	169.0 (4)
N4—Ni1—N1—C2	90.2 (3)	N4—Ni1—O5—C16	−69 (3)
N2—Ni1—N1—C2	−2.1 (3)	N2—Ni1—O5—C16	92.8 (4)
O5—Ni1—N1—O1	92.8 (3)	O1—N1—C2—C3	−179.6 (3)
O3—Ni1—N1—O1	3.1 (3)	Ni1—N1—C2—C3	4.3 (4)
N3—Ni1—N1—O1	−132.2 (4)	O1—N1—C2—C1	1.9 (5)
N4—Ni1—N1—O1	−85.4 (3)	Ni1—N1—C2—C1	−174.1 (3)
N2—Ni1—N1—O1	−177.7 (3)	C7—N2—C3—C4	1.3 (5)
O5—Ni1—N2—C7	−89.8 (3)	Ni1—N2—C3—C4	−176.2 (3)
O3—Ni1—N2—C7	−125 (6)	C7—N2—C3—C2	−179.4 (3)
N3—Ni1—N2—C7	12.8 (3)	Ni1—N2—C3—C2	3.0 (4)
N1—Ni1—N2—C7	−178.0 (3)	N1—C2—C3—N2	−4.8 (5)
N4—Ni1—N2—C7	89.6 (3)	C1—C2—C3—N2	173.7 (3)
O5—Ni1—N2—C3	87.6 (3)	N1—C2—C3—C4	174.5 (4)
O3—Ni1—N2—C3	53 (6)	C1—C2—C3—C4	−7.0 (6)
N3—Ni1—N2—C3	−169.9 (2)	N2—C3—C4—C5	−1.3 (6)
N1—Ni1—N2—C3	−0.7 (2)	C2—C3—C4—C5	179.4 (4)
N4—Ni1—N2—C3	−93.0 (3)	C3—C4—C5—C6	0.4 (7)
O5—Ni1—N3—C9	178.4 (3)	C4—C5—C6—C7	0.5 (7)
O3—Ni1—N3—C9	−91.9 (3)	C3—N2—C7—C6	−0.4 (6)
N1—Ni1—N3—C9	44.9 (5)	Ni1—N2—C7—C6	176.8 (3)
N4—Ni1—N3—C9	−3.5 (3)	C5—C6—C7—N2	−0.5 (7)
N2—Ni1—N3—C9	88.8 (3)	O2—N3—C9—C10	−179.8 (3)
O5—Ni1—N3—O2	2.9 (3)	Ni1—N3—C9—C10	4.1 (4)
O3—Ni1—N3—O2	92.5 (3)	O2—N3—C9—C8	0.3 (5)
N1—Ni1—N3—O2	−130.7 (4)	Ni1—N3—C9—C8	−175.7 (3)
N4—Ni1—N3—O2	−179.1 (3)	C14—N4—C10—C11	−0.8 (5)
N2—Ni1—N3—O2	−86.8 (3)	Ni1—N4—C10—C11	−177.8 (3)
O5—Ni1—N4—C14	−105 (3)	C14—N4—C10—C9	176.2 (3)
O3—Ni1—N4—C14	−86.4 (3)	Ni1—N4—C10—C9	−0.8 (4)
N3—Ni1—N4—C14	−174.6 (3)	N3—C9—C10—N4	−2.1 (5)
N1—Ni1—N4—C14	16.7 (3)	C8—C9—C10—N4	177.7 (3)
N2—Ni1—N4—C14	93.1 (3)	N3—C9—C10—C11	174.8 (3)
O5—Ni1—N4—C10	72 (3)	C8—C9—C10—C11	−5.3 (6)
O3—Ni1—N4—C10	90.4 (2)	N4—C10—C11—C12	0.9 (6)
N3—Ni1—N4—C10	2.2 (2)	C9—C10—C11—C12	−175.8 (4)
N1—Ni1—N4—C10	−166.5 (2)	C10—C11—C12—C13	0.3 (6)
N2—Ni1—N4—C10	−90.2 (2)	C11—C12—C13—C14	−1.4 (6)
O5—Ni1—O3—C15	−100.5 (4)	C10—N4—C14—C13	−0.5 (5)
N3—Ni1—O3—C15	156.9 (4)	Ni1—N4—C14—C13	176.2 (3)
N1—Ni1—O3—C15	−12.4 (4)	C12—C13—C14—N4	1.6 (6)
N4—Ni1—O3—C15	80.1 (4)	Ni1—O3—C15—O4	9.0 (7)
N2—Ni1—O3—C15	−66 (6)	Ni1—O5—C16—O6	−5.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.69	2.508 (4)	177
O2—H2···O6	0.82	1.67	2.482 (4)	169

Experimental details

Crystal data
Chemical formula	[Ni(CHO₂)₂(C₇H₈N₂O)₂]
M_r	421.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.5000 (12), 14.6109 (16), 15.7391 (17)
β (°)	131.850 (2)
V (Å³)	1798.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.20 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.807, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	9294, 3171, 2209
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.137, 1.00
No. of reflections	3171
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.38

Computer programs: SMART (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
O1—H1···O4	0.82	1.69	2.508 (4)	177.4
O2—H2···O6	0.82	1.67	2.482 (4)	168.7

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 20671048, 21041002) and the Shandong Province Higher School Science and Technology Plan Projects (No. J10LB61).

References

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