Bis(acetato-κO)bis­(pyridine-2-aldoxime-κ2N,N′)nickel(II)

Si, Y.

doi:10.1107/S1600536812014377

Bis(acetato-κO)bis(pyridine-2-aldoxime-κ²N,N′)nickel(II)

In the mononuclear title compound, [Ni(CH₃COO)₂(C₆H₆N₂O)₂], the Ni^II atom is coordinated by two pyridine-2-aldoxime (PaoH) ligands and two acetate groups, with cis coordination for the pairs of identical ligands. While each acetate group binds to the Ni^II atom by one O atom, each PaoH chelates the Ni^II atom through two N atoms. The O atom on PaoH is not deprotonated and does not participate in bonding to the Ni^II atom. Thus, the Ni^II atom exhibits an octahedral environment. Intramolecular O—H⋯O hydrogen-bonding interactions and intermolecular C—H⋯O hydrogen-bonding interactions are present in the structure. Adjacent molecules pack along [100] through van der Waals forces.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812014377/ru2032sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812014377/ru2032Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S1600536812014377/ru2032Isup3.cdx Supplementary material

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.113
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          6
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          2
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C15
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N3  -NI1 -O6  -C16   -30.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N1  -NI1 -O4  -C14   -18.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         12
            O6  -NI1 -N3  -C7     18.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            O6  -NI1 -N3  -C11     5.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            O4  -NI1 -N1  -C1   -154.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         36
            O4  -NI1 -N1  -C5     24.00  5.00   1.555   1.555   1.555   1.555

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Ni(PaoH)₂Cl₂ is a good coordination donor building for assembly with transition metal ions, like Mn²⁺. The reaction of Ni(PaoH)₂Cl₂ and Mn(OAc)₂.4H₂O afforded, unexpectedly, the title compound, in which AcO^- is substituted for Cl^-.

Cis coordination fashion was found for the identical ligands. The average Ni—N bond length is 2.095 (18) Å, and the average Fe—O bond length is 2.060 (1) Å. The O atoms on PaoH remain protonated, and intramolecular O—H···O hydrogen-bonds are present, with the acceptor O atom from acetate.

Related literature top

For related literature [on what subject?], see: Krause & Busch (1960); Miyasaka et al. (2004).

Experimental top

Ni(PaoH)₂Cl₂ (0.19 g, 0.5 mmol) and Mn(OAc)₂.4H₂O (0.24 g, 1 mmol) were dissolved in DMF (1 mL) and MeOH (15 mL), then the mixture was stirred for 1 h, followed by filtration. After standing in air for 3 days, well shaped light purple crystals were obtained from the solution.

Structure description top

For related literature [on what subject?], see: Krause & Busch (1960); Miyasaka et al. (2004).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 20% probability displacement ellipsoids for all non-H atoms (H atoms omitted).

Bis(acetato-κO)bis(pyridine-2-aldoxime- κ²N,N')nickel(II) top

Crystal data top

[Ni(C₂H₃O₂)₂(C₆H₆N₂O)₂]	F(000) = 872
M_r = 421.05	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1810 reflections
a = 8.649 (4) Å	θ = 2.7–27.5°
b = 13.707 (7) Å	µ = 1.09 mm⁻¹
c = 17.775 (7) Å	T = 293 K
β = 119.051 (17)°	Prism, light purple
V = 1842.1 (15) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	4207 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
CCD_Profile_fitting scans	h = −9→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −16→17
T_min = 0.809, T_max = 1.000	l = −23→23
14112 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0526P)² + 0.2764P] where P = (F_o² + 2F_c²)/3
4207 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Ni(C₂H₃O₂)₂(C₆H₆N₂O)₂]	V = 1842.1 (15) Å³
M_r = 421.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.649 (4) Å	µ = 1.09 mm⁻¹
b = 13.707 (7) Å	T = 293 K
c = 17.775 (7) Å	0.20 × 0.20 × 0.20 mm
β = 119.051 (17)°

Data collection top

Rigaku Mercury2 diffractometer	4207 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3298 reflections with I > 2σ(I)
T_min = 0.809, T_max = 1.000	R_int = 0.035
14112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
4207 reflections	Δρ_min = −0.37 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	0.00171 (4)	0.80019 (2)	0.15100 (2)	0.03476 (13)
O3	0.3495 (3)	0.88769 (19)	0.33957 (15)	0.0740 (7)
O5	−0.4089 (3)	0.87646 (17)	0.10176 (16)	0.0686 (7)
O6	−0.1317 (2)	0.92515 (14)	0.14997 (13)	0.0499 (5)
O1	0.3372 (3)	0.92561 (17)	0.19987 (14)	0.0627 (6)
H1A	0.3453	0.9146	0.2470	0.094*
O4	0.1120 (3)	0.79396 (15)	0.28287 (12)	0.0531 (5)
O2	−0.3346 (2)	0.70350 (14)	0.13957 (13)	0.0493 (5)
H2A	−0.3671	0.7602	0.1271	0.074*
N3	0.1359 (3)	0.67005 (16)	0.15232 (14)	0.0391 (5)
N2	0.1841 (3)	0.88691 (16)	0.13709 (15)	0.0408 (5)
N1	−0.1082 (3)	0.80866 (15)	0.01696 (14)	0.0370 (5)
N4	−0.1728 (3)	0.69206 (16)	0.14512 (14)	0.0385 (5)
C15	−0.3523 (4)	1.0447 (2)	0.1205 (2)	0.0618 (8)
H15A	−0.4773	1.0458	0.1004	0.093*
H15B	−0.3272	1.0807	0.0813	0.093*
H15C	−0.2909	1.0738	0.1766	0.093*
C3	−0.2199 (5)	0.8366 (3)	−0.1565 (2)	0.0603 (8)
H3A	−0.2570	0.8451	−0.2147	0.072*
C16	−0.2919 (4)	0.9406 (2)	0.12523 (19)	0.0482 (7)
C7	0.2866 (3)	0.6588 (2)	0.14993 (18)	0.0443 (6)
H7A	0.3472	0.7145	0.1490	0.053*
C4	−0.0615 (4)	0.8770 (2)	−0.0945 (2)	0.0558 (8)
H4A	0.0081	0.9139	−0.1104	0.067*
C11	0.0493 (3)	0.5883 (2)	0.15438 (18)	0.0428 (6)
C2	−0.3204 (4)	0.7842 (2)	−0.1307 (2)	0.0547 (8)
H2B	−0.4277	0.7574	−0.1711	0.066*
C14	0.2413 (4)	0.8323 (2)	0.34460 (18)	0.0436 (6)
C1	−0.2604 (3)	0.7717 (2)	−0.04356 (18)	0.0450 (6)
H1B	−0.3294	0.7358	−0.0266	0.054*
C13	0.2694 (4)	0.8122 (2)	0.4337 (2)	0.0619 (9)
H13A	0.1793	0.7685	0.4302	0.093*
H13B	0.2633	0.8723	0.4599	0.093*
H13C	0.3835	0.7829	0.4679	0.093*
C5	−0.0093 (4)	0.86133 (19)	−0.00854 (18)	0.0413 (6)
C12	−0.1192 (4)	0.6044 (2)	0.15257 (19)	0.0478 (7)
H12A	−0.1846	0.5528	0.1567	0.057*
C6	0.1540 (4)	0.9011 (2)	0.06049 (19)	0.0463 (7)
H6A	0.2330	0.9355	0.0491	0.056*
C9	0.2713 (4)	0.4870 (2)	0.1523 (2)	0.0652 (9)
H9A	0.3170	0.4256	0.1522	0.078*
C8	0.3571 (4)	0.5693 (2)	0.1487 (2)	0.0549 (8)
H8A	0.4611	0.5648	0.1456	0.066*
C10	0.1161 (4)	0.4964 (2)	0.1560 (2)	0.0607 (9)
H10A	0.0572	0.4413	0.1595	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03189 (19)	0.0365 (2)	0.0371 (2)	−0.00362 (13)	0.01775 (15)	0.00059 (14)
O3	0.0659 (14)	0.0939 (19)	0.0554 (14)	−0.0353 (14)	0.0241 (11)	−0.0081 (13)
O5	0.0434 (12)	0.0570 (14)	0.1006 (19)	0.0026 (10)	0.0311 (12)	0.0034 (13)
O6	0.0412 (10)	0.0474 (11)	0.0631 (13)	0.0031 (8)	0.0270 (9)	−0.0046 (10)
O1	0.0501 (12)	0.0747 (15)	0.0596 (14)	−0.0285 (11)	0.0237 (10)	−0.0104 (11)
O4	0.0481 (11)	0.0691 (14)	0.0347 (11)	−0.0148 (10)	0.0142 (9)	−0.0021 (9)
O2	0.0356 (10)	0.0568 (13)	0.0626 (13)	−0.0030 (8)	0.0294 (9)	0.0071 (10)
N3	0.0350 (11)	0.0385 (12)	0.0424 (13)	−0.0019 (9)	0.0177 (9)	0.0026 (10)
N2	0.0339 (11)	0.0389 (12)	0.0492 (14)	−0.0081 (9)	0.0197 (10)	−0.0029 (10)
N1	0.0394 (11)	0.0374 (12)	0.0374 (12)	−0.0007 (9)	0.0212 (9)	0.0016 (9)
N4	0.0326 (11)	0.0460 (13)	0.0390 (12)	−0.0071 (9)	0.0190 (9)	0.0030 (10)
C15	0.0566 (18)	0.0544 (19)	0.069 (2)	0.0126 (15)	0.0265 (16)	−0.0026 (16)
C3	0.078 (2)	0.064 (2)	0.0404 (17)	0.0078 (17)	0.0296 (16)	0.0033 (15)
C16	0.0484 (16)	0.0555 (18)	0.0450 (16)	0.0083 (14)	0.0262 (13)	0.0021 (13)
C7	0.0359 (13)	0.0438 (15)	0.0555 (18)	0.0003 (12)	0.0239 (12)	0.0057 (13)
C4	0.074 (2)	0.0536 (19)	0.0545 (19)	0.0053 (15)	0.0422 (17)	0.0089 (15)
C11	0.0411 (14)	0.0374 (14)	0.0460 (16)	−0.0049 (11)	0.0181 (12)	0.0027 (12)
C2	0.0577 (18)	0.0531 (18)	0.0430 (17)	0.0019 (14)	0.0163 (14)	−0.0033 (14)
C14	0.0427 (14)	0.0414 (15)	0.0425 (16)	0.0054 (12)	0.0174 (12)	−0.0025 (12)
C1	0.0414 (14)	0.0475 (16)	0.0422 (16)	−0.0017 (12)	0.0173 (12)	0.0017 (13)
C13	0.064 (2)	0.073 (2)	0.0407 (17)	−0.0059 (16)	0.0194 (15)	−0.0016 (15)
C5	0.0504 (15)	0.0373 (14)	0.0450 (16)	0.0023 (12)	0.0301 (13)	0.0005 (12)
C12	0.0435 (15)	0.0425 (16)	0.0609 (19)	−0.0096 (12)	0.0280 (13)	0.0055 (13)
C6	0.0483 (15)	0.0457 (16)	0.0550 (18)	−0.0081 (12)	0.0331 (14)	0.0019 (13)
C9	0.0530 (18)	0.0430 (17)	0.093 (3)	0.0070 (14)	0.0307 (18)	−0.0010 (17)
C8	0.0417 (15)	0.0550 (18)	0.071 (2)	0.0072 (13)	0.0297 (15)	0.0049 (16)
C10	0.0506 (17)	0.0384 (16)	0.089 (3)	−0.0057 (13)	0.0307 (17)	−0.0003 (16)

Geometric parameters (Å, º) top

Ni1—O4	2.059 (2)	C3—C2	1.367 (5)
Ni1—O6	2.061 (2)	C3—C4	1.390 (5)
Ni1—N4	2.081 (2)	C3—H3A	0.9300
Ni1—N2	2.084 (2)	C7—C8	1.375 (4)
Ni1—N1	2.096 (2)	C7—H7A	0.9300
Ni1—N3	2.122 (2)	C4—C5	1.383 (4)
O3—C14	1.241 (3)	C4—H4A	0.9300
O5—C16	1.249 (4)	C11—C10	1.380 (4)
O6—C16	1.252 (3)	C11—C12	1.459 (4)
O1—N2	1.358 (3)	C2—C1	1.384 (4)
O1—H1A	0.8200	C2—H2B	0.9300
O4—C14	1.241 (3)	C14—C13	1.507 (4)
O2—N4	1.364 (3)	C1—H1B	0.9300
O2—H2A	0.8200	C13—H13A	0.9600
N3—C7	1.333 (3)	C13—H13B	0.9600
N3—C11	1.358 (3)	C13—H13C	0.9600
N2—C6	1.271 (3)	C5—C6	1.454 (4)
N1—C1	1.331 (3)	C12—H12A	0.9300
N1—C5	1.355 (3)	C6—H6A	0.9300
N4—C12	1.272 (3)	C9—C8	1.368 (4)
C15—C16	1.507 (4)	C9—C10	1.381 (4)
C15—H15A	0.9600	C9—H9A	0.9300
C15—H15B	0.9600	C8—H8A	0.9300
C15—H15C	0.9600	C10—H10A	0.9300

O4—Ni1—O6	89.56 (9)	N3—C7—C8	123.4 (3)
O4—Ni1—N4	87.21 (8)	N3—C7—H7A	118.3
O6—Ni1—N4	101.66 (9)	C8—C7—H7A	118.3
O4—Ni1—N2	101.53 (8)	C5—C4—C3	118.8 (3)
O6—Ni1—N2	88.73 (9)	C5—C4—H4A	120.6
N4—Ni1—N2	166.55 (9)	C3—C4—H4A	120.6
O4—Ni1—N1	179.06 (8)	N3—C11—C10	121.5 (3)
O6—Ni1—N1	90.05 (8)	N3—C11—C12	115.7 (2)
N4—Ni1—N1	93.71 (8)	C10—C11—C12	122.8 (3)
N2—Ni1—N1	77.60 (9)	C3—C2—C1	119.1 (3)
O4—Ni1—N3	90.23 (9)	C3—C2—H2B	120.4
O6—Ni1—N3	179.02 (8)	C1—C2—H2B	120.4
N4—Ni1—N3	77.37 (9)	O4—C14—O3	125.7 (3)
N2—Ni1—N3	92.24 (9)	O4—C14—C13	117.9 (3)
N1—Ni1—N3	90.17 (8)	O3—C14—C13	116.4 (3)
C16—O6—Ni1	131.6 (2)	N1—C1—C2	122.9 (3)
N2—O1—H1A	109.5	N1—C1—H1B	118.5
C14—O4—Ni1	135.2 (2)	C2—C1—H1B	118.5
N4—O2—H2A	109.5	C14—C13—H13A	109.5
C7—N3—C11	117.8 (2)	C14—C13—H13B	109.5
C7—N3—Ni1	129.37 (19)	H13A—C13—H13B	109.5
C11—N3—Ni1	112.80 (17)	C14—C13—H13C	109.5
C6—N2—O1	115.6 (2)	H13A—C13—H13C	109.5
C6—N2—Ni1	116.18 (18)	H13B—C13—H13C	109.5
O1—N2—Ni1	128.13 (18)	N1—C5—C4	122.1 (3)
C1—N1—C5	118.0 (2)	N1—C5—C6	115.5 (2)
C1—N1—Ni1	128.49 (18)	C4—C5—C6	122.4 (3)
C5—N1—Ni1	113.46 (17)	N4—C12—C11	117.0 (2)
C12—N4—O2	115.2 (2)	N4—C12—H12A	121.5
C12—N4—Ni1	116.72 (18)	C11—C12—H12A	121.5
O2—N4—Ni1	127.99 (16)	N2—C6—C5	117.2 (2)
C16—C15—H15A	109.5	N2—C6—H6A	121.4
C16—C15—H15B	109.5	C5—C6—H6A	121.4
H15A—C15—H15B	109.5	C8—C9—C10	119.1 (3)
C16—C15—H15C	109.5	C8—C9—H9A	120.4
H15A—C15—H15C	109.5	C10—C9—H9A	120.4
H15B—C15—H15C	109.5	C9—C8—C7	118.7 (3)
C2—C3—C4	119.0 (3)	C9—C8—H8A	120.6
C2—C3—H3A	120.5	C7—C8—H8A	120.6
C4—C3—H3A	120.5	C11—C10—C9	119.4 (3)
O5—C16—O6	125.2 (3)	C11—C10—H10A	120.3
O5—C16—C15	116.4 (3)	C9—C10—H10A	120.3
O6—C16—C15	118.3 (3)

O4—Ni1—O6—C16	−108.2 (3)	N2—Ni1—N4—C12	46.2 (5)
N4—Ni1—O6—C16	−21.1 (3)	N1—Ni1—N4—C12	95.3 (2)
N2—Ni1—O6—C16	150.2 (3)	N3—Ni1—N4—C12	6.0 (2)
N1—Ni1—O6—C16	72.6 (3)	O4—Ni1—N4—O2	90.6 (2)
N3—Ni1—O6—C16	−30 (5)	O6—Ni1—N4—O2	1.7 (2)
O6—Ni1—O4—C14	−83.6 (3)	N2—Ni1—N4—O2	−138.3 (3)
N4—Ni1—O4—C14	174.7 (3)	N1—Ni1—N4—O2	−89.1 (2)
N2—Ni1—O4—C14	5.0 (3)	N3—Ni1—N4—O2	−178.5 (2)
N1—Ni1—O4—C14	−18 (5)	Ni1—O6—C16—O5	7.5 (5)
N3—Ni1—O4—C14	97.3 (3)	Ni1—O6—C16—C15	−170.6 (2)
O4—Ni1—N3—C7	−98.1 (2)	C11—N3—C7—C8	0.6 (4)
O6—Ni1—N3—C7	−176 (100)	Ni1—N3—C7—C8	−178.1 (2)
N4—Ni1—N3—C7	174.8 (3)	C2—C3—C4—C5	1.1 (5)
N2—Ni1—N3—C7	3.4 (2)	C7—N3—C11—C10	1.5 (4)
N1—Ni1—N3—C7	81.0 (2)	Ni1—N3—C11—C10	−179.7 (2)
O4—Ni1—N3—C11	83.15 (19)	C7—N3—C11—C12	−177.0 (2)
O6—Ni1—N3—C11	5 (5)	Ni1—N3—C11—C12	1.8 (3)
N4—Ni1—N3—C11	−3.93 (17)	C4—C3—C2—C1	−1.0 (5)
N2—Ni1—N3—C11	−175.29 (19)	Ni1—O4—C14—O3	−2.7 (5)
N1—Ni1—N3—C11	−97.69 (19)	Ni1—O4—C14—C13	176.1 (2)
O4—Ni1—N2—C6	177.5 (2)	C5—N1—C1—C2	0.4 (4)
O6—Ni1—N2—C6	−93.2 (2)	Ni1—N1—C1—C2	178.6 (2)
N4—Ni1—N2—C6	47.8 (5)	C3—C2—C1—N1	0.2 (5)
N1—Ni1—N2—C6	−2.9 (2)	C1—N1—C5—C4	−0.2 (4)
N3—Ni1—N2—C6	86.8 (2)	Ni1—N1—C5—C4	−178.6 (2)
O4—Ni1—N2—O1	1.8 (2)	C1—N1—C5—C6	179.1 (2)
O6—Ni1—N2—O1	91.1 (2)	Ni1—N1—C5—C6	0.6 (3)
N4—Ni1—N2—O1	−128.0 (4)	C3—C4—C5—N1	−0.6 (4)
N1—Ni1—N2—O1	−178.6 (2)	C3—C4—C5—C6	−179.8 (3)
N3—Ni1—N2—O1	−88.9 (2)	O2—N4—C12—C11	177.0 (2)
O4—Ni1—N1—C1	−154 (5)	Ni1—N4—C12—C11	−6.9 (3)
O6—Ni1—N1—C1	−88.5 (2)	N3—C11—C12—N4	3.3 (4)
N4—Ni1—N1—C1	13.2 (2)	C10—C11—C12—N4	−175.2 (3)
N2—Ni1—N1—C1	−177.2 (2)	O1—N2—C6—C5	−179.6 (2)
N3—Ni1—N1—C1	90.6 (2)	Ni1—N2—C6—C5	4.1 (3)
O4—Ni1—N1—C5	24 (5)	N1—C5—C6—N2	−3.2 (4)
O6—Ni1—N1—C5	89.74 (18)	C4—C5—C6—N2	176.1 (3)
N4—Ni1—N1—C5	−168.57 (18)	C10—C9—C8—C7	0.7 (5)
N2—Ni1—N1—C5	1.04 (17)	N3—C7—C8—C9	−1.7 (5)
N3—Ni1—N1—C5	−91.21 (18)	N3—C11—C10—C9	−2.3 (5)
O4—Ni1—N4—C12	−84.9 (2)	C12—C11—C10—C9	176.1 (3)
O6—Ni1—N4—C12	−173.8 (2)	C8—C9—C10—C11	1.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3	0.82	1.67	2.488 (4)	176
O2—H2A···O5	0.82	1.65	2.463 (3)	173
C3—H3A···O2ⁱ	0.93	2.43	3.307 (4)	157

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₂H₃O₂)₂(C₆H₆N₂O)₂]
M_r	421.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.649 (4), 13.707 (7), 17.775 (7)
β (°)	119.051 (17)
V (Å³)	1842.1 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.809, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14112, 4207, 3298
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.113, 1.08
No. of reflections	4207
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.37

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ni1—O4	2.059 (2)	Ni1—N2	2.084 (2)
Ni1—O6	2.061 (2)	Ni1—N1	2.096 (2)
Ni1—N4	2.081 (2)	Ni1—N3	2.122 (2)