Diaqua-[5,5'-dicarb-oxy-2,2'-(propane-1,3-di-yl)bis-(1H-imidazole-4-carboxyl-ato)]nickel(II) dihydrate.

In the title complex, [Ni(C(13)H(10)N(4)O(8))(H(2)O)(2)]·2H(2)O, the Ni(2+) cation is six-coordinated by two N atoms and two O atoms from the tetra-dentate anion in equatorial positions and by two water O atoms in axial positions, leading to a distorted octa-hedral environment. The central C atom of the propanediyl unit is disordered over two sites in a 0.531 (6):0.469 (6) ratio. In the crystal, adjacent mol-ecules are linked through O-H⋯O and N-H⋯O hydrogen-bonding inter-actions into a three-dimensional network.

Related literature

For background to complexes based on 1H-imidazole-4,5-dicarb­oxy­lic acid, see: Baures et al. (2002 ▶); Sun & Yang (2007 ▶).

Experimental

Crystal data

[Ni(C13H10N4O8)(H2O)2]·2H2O

M = 481.02

Triclinic,

a = 8.9852 (18) Å

b = 9.4392 (19) Å

c = 12.538 (3) Å

α = 108.81 (3)°

β = 92.34 (3)°

γ = 116.18 (3)°

V = 882.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.18 mm−1

T = 293 K

0.21 × 0.18 × 0.15 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.790, T max = 0.843

9532 measured reflections

3451 independent reflections

3037 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.02

3451 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024391/wm2496sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024391/wm2496Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C13H10N4O8)(H2O)2]·2H2O	Z = 2
Mr = 481.02	F(000) = 496
Triclinic, P1	Dx = 1.811 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9852 (18) Å	Cell parameters from 2450 reflections
b = 9.4392 (19) Å	θ = 2.6–27.9°
c = 12.538 (3) Å	µ = 1.18 mm−1
α = 108.81 (3)°	T = 293 K
β = 92.34 (3)°	Prism, green
γ = 116.18 (3)°	0.21 × 0.18 × 0.15 mm
V = 882.1 (5) Å3

Rigaku Saturn diffractometer	3451 independent reflections
Radiation source: fine-focus sealed tube	3037 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 28.5714 pixels mm-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −11→11
Tmin = 0.790, Tmax = 0.843	l = −15→15
9532 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.056P)2 + 0.3821P] where P = (Fo2 + 2Fc2)/3
3451 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	−0.42402 (4)	0.90838 (4)	0.72525 (3)	0.02527 (13)
N1	−0.3010 (3)	0.8092 (3)	0.79563 (19)	0.0263 (5)
N2	−0.1769 (3)	0.6933 (3)	0.8643 (2)	0.0316 (5)
H2	−0.1639	0.6220	0.8872	0.038*
N3	−0.6835 (3)	0.7484 (3)	0.69036 (17)	0.0230 (5)
N4	−0.9581 (3)	0.5817 (3)	0.65436 (18)	0.0251 (5)
H4	−1.0542	0.4986	0.6509	0.030*
O1	−0.1678 (2)	1.1022 (3)	0.75887 (18)	0.0361 (5)
O2	0.0976 (2)	1.1730 (3)	0.8274 (2)	0.0443 (5)
O3	0.2406 (2)	1.0420 (3)	0.90408 (18)	0.0382 (5)
H3	0.1934	1.0939	0.8789	0.046*
O4	0.1688 (3)	0.8133 (3)	0.94778 (18)	0.0394 (5)
O5	−0.5025 (2)	1.0349 (2)	0.65068 (17)	0.0319 (4)
O6	−0.7326 (2)	1.0223 (3)	0.56576 (19)	0.0371 (5)
O7	−1.0474 (2)	0.8392 (3)	0.5275 (2)	0.0451 (6)
H7	−0.9373	0.9087	0.5364	0.054*
O8	−1.2265 (2)	0.6084 (2)	0.55412 (17)	0.0356 (5)
O9	−0.4159 (2)	0.7760 (2)	0.55768 (16)	0.0303 (4)
H9A	−0.3629	0.7202	0.5567	0.036*
H9B	−0.3671	0.8430	0.5235	0.036*
O10	−0.4382 (2)	1.0567 (3)	0.88393 (17)	0.0436 (5)
H10A	−0.5282	1.0618	0.8968	0.052*
H10B	−0.3653	1.0951	0.9453	0.052*
O11	−0.2803 (3)	0.3396 (3)	0.6349 (2)	0.0513 (6)
H11A	−0.3282	0.2375	0.6319	0.062*
H11B	−0.3368	0.3486	0.5839	0.062*
O12	0.1580 (4)	0.5672 (3)	1.0849 (3)	0.0723 (8)
H12A	0.1773	0.6568	1.1416	0.087*
H12B	0.2033	0.6225	1.0429	0.087*
C1	−0.0641 (3)	1.0721 (4)	0.8012 (2)	0.0301 (6)
C2	−0.1280 (3)	0.9137 (3)	0.8225 (2)	0.0247 (5)
C3	−0.0494 (3)	0.8432 (3)	0.8655 (2)	0.0260 (6)
C4	0.1325 (3)	0.9006 (3)	0.9095 (2)	0.0279 (6)
C5	−0.3264 (3)	0.6761 (4)	0.8214 (3)	0.0331 (6)
C6	−0.4936 (4)	0.5266 (5)	0.8043 (4)	0.0640 (10)
H6BC	−0.4708	0.4323	0.7944	0.077*	0.531 (6)
H6BD	−0.5280	0.5511	0.8775	0.077*	0.531 (6)
H6AA	−0.4784	0.4641	0.8480	0.077*	0.469 (6)
H6AB	−0.5309	0.4519	0.7234	0.077*	0.469 (6)
C7	−0.6258 (7)	0.5718 (7)	0.8422 (5)	0.0250 (14)	0.469 (6)
H7A	−0.5750	0.6952	0.8718	0.030*	0.469 (6)
H7B	−0.6568	0.5367	0.9063	0.030*	0.469 (6)
C8	−0.7859 (4)	0.5000 (4)	0.7560 (3)	0.0435 (8)
H8BC	−0.8907	0.3927	0.7314	0.052*	0.531 (6)
H8BD	−0.7651	0.5553	0.8391	0.052*	0.531 (6)
H8AA	−0.8817	0.4600	0.7918	0.052*	0.469 (6)
H8AB	−0.7941	0.4006	0.6950	0.052*	0.469 (6)
C9	−0.8044 (3)	0.6107 (3)	0.7005 (2)	0.0241 (5)
C10	−0.9358 (3)	0.7068 (3)	0.6140 (2)	0.0242 (5)
C11	−1.0812 (3)	0.7141 (3)	0.5620 (2)	0.0284 (6)
C12	−0.7641 (3)	0.8093 (3)	0.6366 (2)	0.0234 (5)
C13	−0.6606 (3)	0.9664 (3)	0.6158 (2)	0.0274 (6)
C7A	−0.6330 (8)	0.4635 (9)	0.7229 (8)	0.0640 (10)	0.531 (6)
H7AA	−0.6791	0.3406	0.6893	0.077*	0.531 (6)
H7AB	−0.5961	0.5056	0.6625	0.077*	0.531 (6)

	U11	U22	U33	U12	U13	U23
Ni1	0.01820 (19)	0.0280 (2)	0.0328 (2)	0.01094 (15)	0.00339 (14)	0.01571 (15)
N1	0.0189 (11)	0.0294 (12)	0.0302 (12)	0.0123 (10)	0.0013 (9)	0.0103 (9)
N2	0.0277 (12)	0.0314 (12)	0.0435 (14)	0.0188 (11)	0.0040 (10)	0.0174 (11)
N3	0.0191 (11)	0.0269 (11)	0.0259 (11)	0.0117 (9)	0.0059 (9)	0.0126 (9)
N4	0.0183 (11)	0.0232 (11)	0.0323 (12)	0.0076 (9)	0.0048 (9)	0.0121 (9)
O1	0.0262 (10)	0.0364 (11)	0.0517 (13)	0.0140 (9)	0.0055 (9)	0.0255 (10)
O2	0.0227 (11)	0.0410 (12)	0.0694 (15)	0.0095 (10)	0.0035 (10)	0.0302 (11)
O3	0.0232 (10)	0.0449 (12)	0.0467 (12)	0.0179 (10)	0.0009 (9)	0.0159 (10)
O4	0.0331 (11)	0.0454 (12)	0.0407 (12)	0.0250 (10)	−0.0046 (9)	0.0101 (10)
O5	0.0209 (10)	0.0324 (10)	0.0471 (12)	0.0105 (8)	0.0052 (8)	0.0241 (9)
O6	0.0275 (10)	0.0453 (12)	0.0551 (13)	0.0196 (10)	0.0099 (9)	0.0358 (10)
O7	0.0218 (10)	0.0520 (13)	0.0728 (16)	0.0158 (10)	0.0044 (10)	0.0407 (12)
O8	0.0208 (10)	0.0348 (11)	0.0493 (13)	0.0116 (9)	0.0028 (9)	0.0168 (9)
O9	0.0265 (10)	0.0386 (11)	0.0373 (11)	0.0191 (9)	0.0108 (8)	0.0226 (9)
O10	0.0279 (11)	0.0621 (14)	0.0340 (11)	0.0262 (11)	0.0004 (9)	0.0040 (10)
O11	0.0313 (12)	0.0441 (13)	0.0710 (16)	0.0043 (10)	0.0005 (11)	0.0341 (12)
O12	0.090 (2)	0.0575 (16)	0.081 (2)	0.0379 (16)	0.0068 (16)	0.0390 (15)
C1	0.0230 (14)	0.0337 (15)	0.0339 (15)	0.0145 (12)	0.0059 (11)	0.0118 (12)
C2	0.0190 (13)	0.0310 (14)	0.0239 (13)	0.0137 (11)	0.0032 (10)	0.0079 (11)
C3	0.0234 (14)	0.0290 (14)	0.0260 (13)	0.0149 (12)	0.0040 (10)	0.0075 (11)
C4	0.0246 (14)	0.0332 (15)	0.0230 (13)	0.0167 (13)	0.0023 (10)	0.0034 (11)
C5	0.0249 (14)	0.0325 (15)	0.0454 (17)	0.0158 (13)	0.0070 (12)	0.0159 (13)
C6	0.0307 (16)	0.0442 (18)	0.118 (3)	0.0155 (15)	0.0163 (18)	0.036 (2)
C7	0.023 (3)	0.029 (3)	0.030 (3)	0.013 (2)	0.006 (2)	0.019 (2)
C8	0.0361 (18)	0.0466 (19)	0.061 (2)	0.0205 (15)	0.0116 (15)	0.0347 (17)
C9	0.0217 (13)	0.0252 (13)	0.0263 (13)	0.0117 (11)	0.0074 (10)	0.0101 (11)
C10	0.0195 (13)	0.0275 (13)	0.0244 (12)	0.0112 (11)	0.0037 (10)	0.0087 (10)
C11	0.0232 (14)	0.0309 (14)	0.0310 (14)	0.0141 (12)	0.0028 (11)	0.0103 (11)
C12	0.0218 (13)	0.0256 (13)	0.0273 (13)	0.0145 (11)	0.0062 (10)	0.0108 (10)
C13	0.0206 (13)	0.0312 (14)	0.0328 (14)	0.0131 (12)	0.0049 (11)	0.0142 (12)
C7A	0.0307 (16)	0.0442 (18)	0.118 (3)	0.0155 (15)	0.0163 (18)	0.036 (2)

Ni1—O5	2.0514 (18)	O11—H11A	0.8504
Ni1—N1	2.060 (2)	O11—H11B	0.8499
Ni1—N3	2.072 (2)	O12—H12A	0.8500
Ni1—O10	2.078 (2)	O12—H12B	0.8499
Ni1—O9	2.093 (2)	C1—C2	1.466 (4)
Ni1—O1	2.128 (2)	C2—C3	1.358 (4)
N1—C5	1.323 (4)	C3—C4	1.491 (4)
N1—C2	1.376 (3)	C5—C6	1.484 (4)
N2—C5	1.346 (3)	C6—C7A	1.346 (8)
N2—C3	1.368 (4)	C6—C7	1.477 (6)
N2—H2	0.8600	C6—H6BC	0.9700
N3—C9	1.325 (3)	C6—H6BD	0.9700
N3—C12	1.374 (3)	C6—H6AA	0.9702
N4—C9	1.348 (3)	C6—H6AB	0.9698
N4—C10	1.369 (3)	C7—C8	1.496 (6)
N4—H4	0.8600	C7—H7A	0.9700
O1—C1	1.234 (3)	C7—H7B	0.9700
O2—C1	1.290 (3)	C8—C9	1.489 (4)
O3—C4	1.284 (4)	C8—C7A	1.596 (7)
O3—H3	0.8899	C8—H8BC	0.9700
O4—C4	1.222 (3)	C8—H8BD	0.9700
O5—C13	1.258 (3)	C8—H8AA	0.9699
O6—C13	1.254 (3)	C8—H8AB	0.9702
O7—C11	1.303 (3)	C10—C12	1.366 (4)
O7—H7	0.8901	C10—C11	1.475 (3)
O8—C11	1.219 (3)	C12—C13	1.478 (4)
O9—H9A	0.8499	C7A—H6AB	0.9711
O9—H9B	0.8499	C7A—H8AB	1.2792
O10—H10A	0.8497	C7A—H7AA	0.9700
O10—H10B	0.8499	C7A—H7AB	0.9700
O5—Ni1—N1	169.24 (8)	C5—C6—H6BD	105.7
O5—Ni1—N3	81.61 (8)	H6BC—C6—H6BD	106.1
N1—Ni1—N3	108.79 (9)	C7A—C6—H6AA	123.7
O5—Ni1—O10	88.48 (9)	C7—C6—H6AA	108.3
N1—Ni1—O10	94.21 (9)	C5—C6—H6AA	108.1
N3—Ni1—O10	89.72 (9)	C7—C6—H6AB	109.8
O5—Ni1—O9	85.09 (8)	C5—C6—H6AB	108.8
N1—Ni1—O9	92.00 (8)	H6BD—C6—H6AB	144.7
N3—Ni1—O9	89.98 (9)	H6AA—C6—H6AB	107.7
O10—Ni1—O9	173.54 (8)	C6—C7—C8	118.4 (4)
O5—Ni1—O1	89.84 (8)	C6—C7—H7A	107.7
N1—Ni1—O1	79.91 (8)	C8—C7—H7A	107.7
N3—Ni1—O1	170.90 (8)	C6—C7—H7B	107.7
O10—Ni1—O1	86.91 (9)	C8—C7—H7B	107.7
O9—Ni1—O1	92.42 (9)	H7A—C7—H7B	107.1
C5—N1—C2	106.1 (2)	C9—C8—C7	118.5 (3)
C5—N1—Ni1	143.02 (19)	C9—C8—C7A	111.2 (4)
C2—N1—Ni1	110.77 (17)	C7—C8—C7A	57.7 (4)
C5—N2—C3	108.5 (2)	C9—C8—H8BC	109.4
C5—N2—H2	125.8	C7—C8—H8BC	131.9
C3—N2—H2	125.8	C7A—C8—H8BC	109.4
C9—N3—C12	106.5 (2)	C9—C8—H8BD	109.4
C9—N3—Ni1	145.05 (18)	C7A—C8—H8BD	109.4
C12—N3—Ni1	108.42 (16)	H8BC—C8—H8BD	108.0
C9—N4—C10	108.6 (2)	C9—C8—H8AA	108.2
C9—N4—H4	125.7	C7—C8—H8AA	108.8
C10—N4—H4	125.7	C7A—C8—H8AA	139.8
C1—O1—Ni1	113.46 (18)	C9—C8—H8AB	107.3
C4—O3—H3	113.8	C7—C8—H8AB	106.4
C13—O5—Ni1	115.03 (17)	H8BC—C8—H8AB	60.8
C11—O7—H7	114.9	H8BD—C8—H8AB	143.2
Ni1—O9—H9A	112.4	H8AA—C8—H8AB	107.1
Ni1—O9—H9B	111.7	N3—C9—N4	110.0 (2)
H9A—O9—H9B	107.0	N3—C9—C8	128.3 (2)
Ni1—O10—H10A	122.8	N4—C9—C8	121.7 (2)
Ni1—O10—H10B	122.2	C12—C10—N4	105.5 (2)
H10A—O10—H10B	113.1	C12—C10—C11	132.8 (2)
H11A—O11—H11B	110.1	N4—C10—C11	121.7 (2)
H12A—O12—H12B	93.0	O8—C11—O7	121.9 (2)
O1—C1—O2	123.1 (3)	O8—C11—C10	120.8 (2)
O1—C1—C2	118.3 (2)	O7—C11—C10	117.3 (2)
O2—C1—C2	118.6 (2)	C10—C12—N3	109.5 (2)
C3—C2—N1	109.7 (2)	C10—C12—C13	131.6 (2)
C3—C2—C1	132.8 (2)	N3—C12—C13	118.9 (2)
N1—C2—C1	117.5 (2)	O6—C13—O5	124.5 (2)
C2—C3—N2	105.5 (2)	O6—C13—C12	119.5 (2)
C2—C3—C4	132.7 (3)	O5—C13—C12	116.0 (2)
N2—C3—C4	121.7 (2)	C6—C7A—C8	120.2 (6)
O4—C4—O3	124.9 (3)	C8—C7A—H6AB	165.8
O4—C4—C3	119.3 (3)	C6—C7A—H8AB	149.0
O3—C4—C3	115.8 (2)	H6AB—C7A—H8AB	151.6
N1—C5—N2	110.2 (2)	C6—C7A—H7AA	107.3
N1—C5—C6	125.8 (3)	C8—C7A—H7AA	107.3
N2—C5—C6	124.0 (3)	H6AB—C7A—H7AA	77.9
C7A—C6—C7	63.7 (4)	H8AB—C7A—H7AA	73.9
C7A—C6—C5	126.5 (5)	C6—C7A—H7AB	107.3
C7—C6—C5	113.9 (3)	C8—C7A—H7AB	107.3
C7A—C6—H6BC	105.7	H6AB—C7A—H7AB	83.1
C7—C6—H6BC	136.7	H8AB—C7A—H7AB	101.6
C5—C6—H6BC	105.7	H7AA—C7A—H7AB	106.9
C7A—C6—H6BD	105.7
N3—Ni1—N1—C5	5.0 (3)	Ni1—N1—C5—N2	177.0 (2)
O10—Ni1—N1—C5	96.1 (3)	C2—N1—C5—C6	−178.3 (3)
O9—Ni1—N1—C5	−85.7 (3)	Ni1—N1—C5—C6	−1.9 (6)
O1—Ni1—N1—C5	−177.8 (3)	C3—N2—C5—N1	−0.5 (3)
O5—Ni1—N1—C2	16.6 (5)	C3—N2—C5—C6	178.4 (3)
N3—Ni1—N1—C2	−178.70 (16)	N1—C5—C6—C7A	29.0 (7)
O10—Ni1—N1—C2	−87.56 (18)	N2—C5—C6—C7A	−149.8 (5)
O9—Ni1—N1—C2	90.65 (18)	N1—C5—C6—C7	−45.1 (6)
O1—Ni1—N1—C2	−1.46 (16)	N2—C5—C6—C7	136.1 (4)
O5—Ni1—N3—C9	−177.6 (3)	C7A—C6—C7—C8	2.0 (5)
N1—Ni1—N3—C9	5.2 (3)	C5—C6—C7—C8	122.5 (4)
O10—Ni1—N3—C9	−89.1 (3)	C6—C7—C8—C9	−100.1 (5)
O9—Ni1—N3—C9	97.3 (3)	C6—C7—C8—C7A	−1.8 (4)
O5—Ni1—N3—C12	1.02 (16)	C12—N3—C9—N4	0.5 (3)
N1—Ni1—N3—C12	−176.13 (15)	Ni1—N3—C9—N4	179.1 (2)
O10—Ni1—N3—C12	89.52 (17)	C12—N3—C9—C8	−177.8 (3)
O9—Ni1—N3—C12	−84.02 (16)	Ni1—N3—C9—C8	0.9 (5)
O5—Ni1—O1—C1	−175.7 (2)	C10—N4—C9—N3	−0.7 (3)
N1—Ni1—O1—C1	1.0 (2)	C10—N4—C9—C8	177.7 (2)
O10—Ni1—O1—C1	95.8 (2)	C7—C8—C9—N3	21.0 (5)
O9—Ni1—O1—C1	−90.7 (2)	C7A—C8—C9—N3	−42.8 (5)
N1—Ni1—O5—C13	163.9 (4)	C7—C8—C9—N4	−157.1 (3)
N3—Ni1—O5—C13	−1.47 (19)	C7A—C8—C9—N4	139.1 (4)
O10—Ni1—O5—C13	−91.4 (2)	C9—N4—C10—C12	0.6 (3)
O9—Ni1—O5—C13	89.2 (2)	C9—N4—C10—C11	−177.8 (2)
O1—Ni1—O5—C13	−178.32 (19)	C12—C10—C11—O8	−177.5 (3)
Ni1—O1—C1—O2	179.6 (2)	N4—C10—C11—O8	0.3 (4)
Ni1—O1—C1—C2	−0.2 (3)	C12—C10—C11—O7	1.2 (4)
C5—N1—C2—C3	−0.4 (3)	N4—C10—C11—O7	179.0 (2)
Ni1—N1—C2—C3	−178.14 (17)	N4—C10—C12—N3	−0.3 (3)
C5—N1—C2—C1	179.5 (2)	C11—C10—C12—N3	177.8 (3)
Ni1—N1—C2—C1	1.8 (3)	N4—C10—C12—C13	−178.8 (3)
O1—C1—C2—C3	178.9 (3)	C11—C10—C12—C13	−0.7 (5)
O2—C1—C2—C3	−1.0 (5)	C9—N3—C12—C10	−0.1 (3)
O1—C1—C2—N1	−1.1 (4)	Ni1—N3—C12—C10	−179.28 (17)
O2—C1—C2—N1	179.0 (2)	C9—N3—C12—C13	178.6 (2)
N1—C2—C3—N2	0.1 (3)	Ni1—N3—C12—C13	−0.6 (3)
C1—C2—C3—N2	−179.9 (3)	Ni1—O5—C13—O6	−178.4 (2)
N1—C2—C3—C4	−178.8 (3)	Ni1—O5—C13—C12	1.5 (3)
C1—C2—C3—C4	1.2 (5)	C10—C12—C13—O6	−2.3 (4)
C5—N2—C3—C2	0.2 (3)	N3—C12—C13—O6	179.3 (2)
C5—N2—C3—C4	179.3 (2)	C10—C12—C13—O5	177.7 (3)
C2—C3—C4—O4	177.4 (3)	N3—C12—C13—O5	−0.6 (4)
N2—C3—C4—O4	−1.4 (4)	C7—C6—C7A—C8	−1.9 (5)
C2—C3—C4—O3	−2.4 (4)	C5—C6—C7A—C8	−103.3 (6)
N2—C3—C4—O3	178.7 (2)	C9—C8—C7A—C6	113.1 (6)
C2—N1—C5—N2	0.6 (3)	C7—C8—C7A—C6	2.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.89	1.60	2.485 (3)	176
O7—H7···O6	0.89	1.62	2.501 (3)	171
O12—H12B···O4	0.85	2.57	3.279 (3)	142
N2—H2···O12i	0.86	1.95	2.802 (3)	171
N4—H4···O11ii	0.86	1.87	2.721 (3)	170
O10—H10A···O3ii	0.85	2.01	2.853 (3)	171
O9—H9A···O8iii	0.85	1.93	2.781 (3)	176
O9—H9A···O7iii	0.85	2.64	3.157 (3)	121
O11—H11B···O8iii	0.85	2.37	2.884 (3)	120
O9—H9B···O6iv	0.85	1.91	2.762 (3)	175
O10—H10B···O4v	0.85	1.84	2.667 (3)	165
O12—H12A···O1v	0.85	2.26	3.063 (4)	159
O12—H12B···O10v	0.85	2.62	3.198 (4)	126
O11—H11A···O5vi	0.85	1.96	2.762 (3)	157
O11—H11B···O9vii	0.85	2.34	3.100 (3)	148

Table 1

Selected bond lengths (Å)

Ni1—O5	2.0514 (18)
Ni1—N1	2.060 (2)
Ni1—N3	2.072 (2)
Ni1—O10	2.078 (2)
Ni1—O9	2.093 (2)
Ni1—O1	2.128 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.89	1.60	2.485 (3)	176
O7—H7⋯O6	0.89	1.62	2.501 (3)	171
O12—H12B⋯O4	0.85	2.57	3.279 (3)	142
N2—H2⋯O12i	0.86	1.95	2.802 (3)	171
N4—H4⋯O11ii	0.86	1.87	2.721 (3)	170
O10—H10A⋯O3ii	0.85	2.01	2.853 (3)	171
O9—H9A⋯O8iii	0.85	1.93	2.781 (3)	176
O9—H9A⋯O7iii	0.85	2.64	3.157 (3)	121
O11—H11B⋯O8iii	0.85	2.37	2.884 (3)	120
O9—H9B⋯O6iv	0.85	1.91	2.762 (3)	175
O10—H10B⋯O4v	0.85	1.84	2.667 (3)	165
O12—H12A⋯O1v	0.85	2.26	3.063 (4)	159
O12—H12B⋯O10v	0.85	2.62	3.198 (4)	126
O11—H11A⋯O5vi	0.85	1.96	2.762 (3)	157
O11—H11B⋯O9vii	0.85	2.34	3.100 (3)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .