Bis(1H-benzimidazole-κN ³)bis­[2-(naphthalen-1-yl)acetato-κ² O,O′]nickel(II) monohydrate

Abstract

In the title compound, [Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O, The Ni^II cation is located on a twofold rotation axis and is six-coordinated in a distorted NiN₂O₄ octa­hedral geometry. The asymmetric unit consists of a nickel(II) ion, one 2-(naphthalen-1-yl)acetate anion, a neutral benzotriazole ligand and one half of a lattice water mol­ecule. The crystal packing is stabilized by O—H⋯O and N—H⋯O hydrogen bonds. The title compound is isotypic with its Cd^II analogue.

Related literature  

For the crystal structures of related 2-(naphthalen-1-yl)acetate complexes, see: Yin et al. (2011a ▶,b ▶); Liu et al. (2007 ▶); Yang et al. (2008 ▶); Tang et al. (2006 ▶); Ji et al. (2011 ▶). For the isotypic Cd^II complex, see: Duan et al. (2007 ▶).

Experimental  

Crystal data  

• [Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O

• M _r = 683.37

• Monoclinic,

• a = 11.573 (4) Å

• b = 19.991 (7) Å

• c = 14.290 (5) Å

• β = 105.903 (4)°

• V = 3179.5 (19) ų

• Z = 4

• Mo Kα radiation

• μ = 0.66 mm⁻¹

• T = 298 K

• 0.10 × 0.10 × 0.10 mm

Data collection  

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.952, T _max = 0.952

• 11840 measured reflections

• 2807 independent reflections

• 1849 reflections with I > 2σ(I)

• R _int = 0.083

Refinement  

• R[F ² > 2σ(F ²)] = 0.050

• wR(F ²) = 0.122

• S = 0.99

• 2807 reflections

• 221 parameters

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.41 e Å⁻³

• Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O4	0.90 (8)	2.24 (8)	2.988 (6)	141 (8)
N2—H2⋯O4i	0.86	2.00	2.791 (4)	152

Symmetry code: (i) .

supplementary crystallographic information

Comment

In recent years particular interest has been devoted to the 1-naphthylacetate ligand in coordination chemistry due to its ability to form metal complexes (Yin et al., 2011a, 2011b; Liu et al.,2007; Yang et al., 2008; Tang et al.,2006 ; Ji et al., 2011). The crystal structure of the title compound was determined as part of an ongoing study of the properties of nickel complexes containing imidazole ligands. In the title mononuclear metal complex, the asymmetric unit consists of a nickel cation, one 2-(naphthalen-1-yl)acetate anion,a benzotriazole ligand, and half of a lattic water molecule. The Ni^II cation is located on a two fold rotation axis and is six coordinated by two N from two benzotriazoles and four O atoms from two different 2-(naphthalen-1-yl)acetate anions, displaying a distorted NiN2O4 octahedral geometry, with Ni-O bond lengths in the range 2.056 (2)-2.288 (2)Å; the Ni-N bond length is 2.020 (3)Å. The crystal packing is stabilized by intermolecular N—H···O hydrogen bonding (Fig. 2) interactions which give rise to a one-dimensional chain structure. An isotypic cadmium(II) structure has been reported previously (Duan et al., 2007).

Experimental

The title compound was synthesized by the reaction ofNi(NO₃)₂.6H₂O, (87.24 mg, 0.3 mmol), 1-naphthylacetic acid(93 mg, 0.5 mmol), benzotriazole (35.4mg, 0.3 mmol) and NaOH (20 mg, 0.5 mmol) in 16 mL of a water-ethanol (2:1) mixture under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 160°C for three days. After cooling colorless the crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol.

Refinement

H atoms were placed in calculated positions, with N–H = 0.86 Å ; C—H = 0.93 Å or C—H = 0.97 Å and refined with a riding model, with U_iso(H) = 1.2U_eq(C).Water H atoms were located in Fourier difference maps and refined isotropically..

Figures

Fig. 1.

Molecule and the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.Hydrogenbonding is shown as dashed lines[Symmetry code: (A) 1-x, y, 1.5-z].

Fig. 2.

Part of the one-dimensional chain structure of (I) formed by N—H···O hydrogen bonds (dashed lines)along [001].

Crystal data

[Ni(C12H9O2)2(C7H6N2)2]·H2O	F(000) = 1424
Mr = 683.37	Dx = 1.428 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1368 reflections
a = 11.573 (4) Å	θ = 3.5–23.4°
b = 19.991 (7) Å	µ = 0.66 mm−1
c = 14.290 (5) Å	T = 298 K
β = 105.903 (4)°	Block, colourless
V = 3179.5 (19) Å3	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	2807 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.952, Tmax = 0.952	k = −23→23
11840 measured reflections	l = −16→16

Refinement

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3
2807 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6876 (3)	0.58948 (19)	0.7714 (2)	0.0396 (9)
C2	0.8061 (3)	0.6268 (2)	0.7974 (3)	0.0527 (10)
H2A	0.8067	0.6572	0.8505	0.063*
H2B	0.8701	0.5946	0.8214	0.063*
C3	0.8350 (3)	0.6664 (2)	0.7174 (3)	0.0460 (9)
C4	0.8408 (3)	0.7344 (2)	0.7213 (3)	0.0585 (11)
H4	0.8252	0.7564	0.7738	0.070*
C5	0.8696 (4)	0.7721 (2)	0.6480 (4)	0.0679 (13)
H5	0.8750	0.8184	0.6533	0.081*
C6	0.8898 (4)	0.7412 (2)	0.5694 (3)	0.0661 (13)
H6	0.9074	0.7667	0.5206	0.079*
C7	0.8844 (3)	0.6714 (2)	0.5609 (3)	0.0507 (10)
C8	0.8573 (3)	0.63328 (19)	0.6355 (3)	0.0433 (9)
C9	0.8534 (3)	0.5631 (2)	0.6255 (3)	0.0525 (11)
H9	0.8374	0.5371	0.6744	0.063*
C10	0.8724 (4)	0.5324 (2)	0.5464 (4)	0.0665 (13)
H10	0.8690	0.4860	0.5416	0.080*
C11	0.8969 (4)	0.5702 (3)	0.4727 (4)	0.0741 (14)
H11	0.9087	0.5489	0.4182	0.089*
C12	0.9039 (3)	0.6382 (3)	0.4795 (3)	0.0666 (13)
H12	0.9216	0.6629	0.4301	0.080*
C13	0.4383 (3)	0.44910 (18)	0.5645 (2)	0.0421 (9)
H13	0.3634	0.4697	0.5500	0.050*
C14	0.5879 (3)	0.38798 (17)	0.5476 (3)	0.0428 (9)
C15	0.6185 (3)	0.41847 (17)	0.6388 (2)	0.0370 (8)
C16	0.7297 (3)	0.40796 (19)	0.7041 (3)	0.0515 (10)
H16	0.7507	0.4278	0.7653	0.062*
C17	0.8083 (4)	0.3663 (2)	0.6737 (4)	0.0638 (12)
H17	0.8842	0.3582	0.7154	0.077*
C18	0.7766 (4)	0.3365 (2)	0.5830 (4)	0.0684 (13)
H18	0.8319	0.3087	0.5658	0.082*
C19	0.6675 (4)	0.34618 (19)	0.5176 (3)	0.0556 (11)
H19	0.6472	0.3261	0.4565	0.067*
N1	0.5211 (2)	0.45750 (13)	0.64759 (19)	0.0380 (7)
N2	0.4725 (3)	0.40802 (14)	0.5028 (2)	0.0434 (8)
H2	0.4300	0.3964	0.4458	0.052*
Ni1	0.5000	0.52246 (3)	0.7500	0.0369 (2)
O2	0.6755 (2)	0.54170 (12)	0.82476 (17)	0.0469 (7)
O4	0.6028 (2)	0.60642 (12)	0.69919 (17)	0.0441 (6)
O1W	0.5000	0.7341 (3)	0.7500	0.163 (4)
H1A	0.541 (8)	0.711 (4)	0.716 (8)	0.245*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.038 (2)	0.052 (2)	0.032 (2)	−0.0045 (18)	0.0159 (17)	−0.0054 (18)
C2	0.042 (2)	0.069 (3)	0.048 (2)	−0.011 (2)	0.0140 (18)	0.000 (2)
C3	0.028 (2)	0.054 (3)	0.056 (2)	−0.0035 (18)	0.0110 (17)	0.001 (2)
C4	0.047 (3)	0.058 (3)	0.073 (3)	−0.003 (2)	0.019 (2)	−0.010 (2)
C5	0.057 (3)	0.047 (3)	0.097 (4)	−0.007 (2)	0.017 (3)	0.012 (3)
C6	0.052 (3)	0.074 (4)	0.074 (3)	−0.004 (2)	0.019 (2)	0.022 (3)
C7	0.032 (2)	0.066 (3)	0.054 (3)	0.001 (2)	0.0117 (18)	0.007 (2)
C8	0.0237 (19)	0.048 (3)	0.057 (2)	0.0011 (17)	0.0101 (17)	0.006 (2)
C9	0.034 (2)	0.057 (3)	0.068 (3)	−0.0009 (19)	0.017 (2)	0.000 (2)
C10	0.042 (3)	0.070 (3)	0.086 (3)	0.011 (2)	0.015 (2)	−0.020 (3)
C11	0.044 (3)	0.109 (4)	0.069 (3)	0.021 (3)	0.014 (2)	−0.021 (3)
C12	0.041 (3)	0.107 (4)	0.055 (3)	0.009 (3)	0.018 (2)	0.009 (3)
C13	0.041 (2)	0.046 (2)	0.042 (2)	−0.0002 (18)	0.0162 (18)	0.0009 (18)
C14	0.049 (2)	0.040 (2)	0.046 (2)	−0.0024 (19)	0.0236 (19)	0.0021 (18)
C15	0.036 (2)	0.038 (2)	0.040 (2)	−0.0002 (17)	0.0171 (17)	0.0012 (17)
C16	0.045 (2)	0.052 (3)	0.058 (3)	0.003 (2)	0.016 (2)	0.002 (2)
C17	0.043 (3)	0.060 (3)	0.088 (3)	0.008 (2)	0.016 (2)	0.004 (3)
C18	0.064 (3)	0.060 (3)	0.094 (4)	0.015 (2)	0.043 (3)	−0.004 (3)
C19	0.064 (3)	0.052 (3)	0.061 (3)	0.000 (2)	0.035 (2)	−0.006 (2)
N1	0.0346 (17)	0.0430 (18)	0.0379 (16)	0.0012 (14)	0.0127 (14)	0.0027 (14)
N2	0.045 (2)	0.0480 (19)	0.0362 (16)	−0.0053 (16)	0.0095 (15)	−0.0029 (15)
Ni1	0.0321 (4)	0.0448 (4)	0.0365 (4)	0.000	0.0142 (3)	0.000
O2	0.0376 (15)	0.0565 (17)	0.0476 (15)	−0.0063 (12)	0.0132 (12)	0.0065 (13)
O4	0.0357 (15)	0.0578 (17)	0.0412 (14)	−0.0039 (12)	0.0143 (12)	−0.0008 (12)
O1W	0.097 (5)	0.066 (4)	0.320 (13)	0.000	0.046 (6)	0.000

Geometric parameters (Å, º)

C1—O2	1.254 (4)	C13—N1	1.316 (4)
C1—O4	1.260 (4)	C13—N2	1.341 (4)
C1—C2	1.516 (5)	C13—H13	0.9300
C1—Ni1	2.498 (4)	C14—N2	1.374 (4)
C2—C3	1.502 (5)	C14—C15	1.394 (5)
C2—H2A	0.9700	C14—C19	1.395 (5)
C2—H2B	0.9700	C15—C16	1.383 (5)
C3—C4	1.361 (5)	C15—N1	1.405 (4)
C3—C8	1.429 (5)	C16—C17	1.389 (5)
C4—C5	1.403 (6)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.382 (6)
C5—C6	1.356 (6)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.364 (6)
C6—C7	1.401 (6)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.410 (5)	N1—Ni1	2.021 (3)
C7—C8	1.413 (5)	N2—H2	0.8600
C8—C9	1.410 (5)	Ni1—N1i	2.021 (3)
C9—C10	1.355 (5)	Ni1—O2	2.055 (2)
C9—H9	0.9300	Ni1—O2i	2.055 (2)
C10—C11	1.386 (6)	Ni1—O4	2.287 (2)
C10—H10	0.9300	Ni1—O4i	2.288 (2)
C11—C12	1.364 (6)	Ni1—C1i	2.498 (4)
C11—H11	0.9300	O1W—H1A	0.90 (8)
C12—H12	0.9300
O2—C1—O4	120.7 (3)	C14—C15—N1	108.8 (3)
O2—C1—C2	118.1 (3)	C15—C16—C17	116.6 (4)
O4—C1—C2	121.2 (3)	C15—C16—H16	121.7
O2—C1—Ni1	55.05 (17)	C17—C16—H16	121.7
O4—C1—Ni1	65.66 (19)	C18—C17—C16	121.6 (4)
C2—C1—Ni1	172.8 (3)	C18—C17—H17	119.2
C3—C2—C1	116.6 (3)	C16—C17—H17	119.2
C3—C2—H2A	108.1	C19—C18—C17	122.7 (4)
C1—C2—H2A	108.1	C19—C18—H18	118.7
C3—C2—H2B	108.1	C17—C18—H18	118.7
C1—C2—H2B	108.1	C18—C19—C14	116.1 (4)
H2A—C2—H2B	107.3	C18—C19—H19	122.0
C4—C3—C8	118.6 (4)	C14—C19—H19	122.0
C4—C3—C2	120.9 (4)	C13—N1—C15	104.6 (3)
C8—C3—C2	120.5 (4)	C13—N1—Ni1	122.2 (2)
C3—C4—C5	121.7 (4)	C15—N1—Ni1	132.9 (2)
C3—C4—H4	119.2	C13—N2—C14	107.3 (3)
C5—C4—H4	119.2	C13—N2—H2	126.4
C6—C5—C4	120.2 (4)	C14—N2—H2	126.4
C6—C5—H5	119.9	N1—Ni1—N1i	100.03 (15)
C4—C5—H5	119.9	N1—Ni1—O2	101.45 (10)
C5—C6—C7	120.8 (4)	N1i—Ni1—O2	92.41 (10)
C5—C6—H6	119.6	N1—Ni1—O2i	92.41 (10)
C7—C6—H6	119.6	N1i—Ni1—O2i	101.45 (10)
C6—C7—C12	121.8 (4)	O2—Ni1—O2i	158.42 (14)
C6—C7—C8	119.1 (4)	N1—Ni1—O4	93.73 (10)
C12—C7—C8	119.1 (4)	N1i—Ni1—O4	151.40 (10)
C9—C8—C7	117.9 (4)	O2—Ni1—O4	60.13 (9)
C9—C8—C3	122.4 (4)	O2i—Ni1—O4	102.90 (9)
C7—C8—C3	119.6 (4)	N1—Ni1—O4i	151.40 (10)
C10—C9—C8	121.7 (4)	N1i—Ni1—O4i	93.73 (10)
C10—C9—H9	119.1	O2—Ni1—O4i	102.90 (9)
C8—C9—H9	119.1	O2i—Ni1—O4i	60.13 (9)
C9—C10—C11	120.1 (4)	O4—Ni1—O4i	85.60 (12)
C9—C10—H10	120.0	N1—Ni1—C1	99.19 (11)
C11—C10—H10	120.0	N1i—Ni1—C1	121.98 (11)
C12—C11—C10	120.6 (4)	O2—Ni1—C1	30.01 (10)
C12—C11—H11	119.7	O2i—Ni1—C1	131.69 (12)
C10—C11—H11	119.7	O4—Ni1—C1	30.12 (10)
C11—C12—C7	120.6 (4)	O4i—Ni1—C1	94.46 (11)
C11—C12—H12	119.7	N1—Ni1—C1i	121.98 (11)
C7—C12—H12	119.7	N1i—Ni1—C1i	99.19 (11)
N1—C13—N2	113.5 (3)	O2—Ni1—C1i	131.69 (12)
N1—C13—H13	123.3	O2i—Ni1—C1i	30.01 (10)
N2—C13—H13	123.3	O4—Ni1—C1i	94.46 (11)
N2—C14—C15	105.9 (3)	O4i—Ni1—C1i	30.12 (10)
N2—C14—C19	132.2 (4)	C1—Ni1—C1i	115.13 (18)
C15—C14—C19	122.0 (4)	C1—O2—Ni1	94.9 (2)
C16—C15—C14	121.1 (3)	C1—O4—Ni1	84.2 (2)
C16—C15—N1	130.1 (3)
O2—C1—C2—C3	159.6 (3)	C13—N1—Ni1—O2	−156.1 (3)
O4—C1—C2—C3	−21.6 (5)	C15—N1—Ni1—O2	16.7 (3)
Ni1—C1—C2—C3	177 (2)	C13—N1—Ni1—O2i	7.2 (3)
C1—C2—C3—C4	113.3 (4)	C15—N1—Ni1—O2i	−180.0 (3)
C1—C2—C3—C8	−66.9 (5)	C13—N1—Ni1—O4	−95.9 (3)
C8—C3—C4—C5	−0.9 (6)	C15—N1—Ni1—O4	76.9 (3)
C2—C3—C4—C5	178.9 (4)	C13—N1—Ni1—O4i	−8.2 (4)
C3—C4—C5—C6	1.7 (6)	C15—N1—Ni1—O4i	164.6 (2)
C4—C5—C6—C7	−1.2 (6)	C13—N1—Ni1—C1	−125.7 (3)
C5—C6—C7—C12	179.4 (4)	C15—N1—Ni1—C1	47.1 (3)
C5—C6—C7—C8	0.1 (6)	C13—N1—Ni1—C1i	1.8 (3)
C6—C7—C8—C9	−179.5 (3)	C15—N1—Ni1—C1i	174.6 (3)
C12—C7—C8—C9	1.2 (5)	O2—C1—Ni1—N1	−97.0 (2)
C6—C7—C8—C3	0.6 (5)	O4—C1—Ni1—N1	81.5 (2)
C12—C7—C8—C3	−178.7 (3)	C2—C1—Ni1—N1	−116 (2)
C4—C3—C8—C9	179.9 (3)	O2—C1—Ni1—N1i	11.0 (2)
C2—C3—C8—C9	0.1 (5)	O4—C1—Ni1—N1i	−170.49 (17)
C4—C3—C8—C7	−0.2 (5)	C2—C1—Ni1—N1i	−8 (2)
C2—C3—C8—C7	−180.0 (3)	O4—C1—Ni1—O2	178.5 (3)
C7—C8—C9—C10	−1.3 (5)	C2—C1—Ni1—O2	−19 (2)
C3—C8—C9—C10	178.6 (4)	O2—C1—Ni1—O2i	161.39 (15)
C8—C9—C10—C11	0.2 (6)	O4—C1—Ni1—O2i	−20.1 (3)
C9—C10—C11—C12	0.9 (6)	C2—C1—Ni1—O2i	142 (2)
C10—C11—C12—C7	−1.0 (6)	O2—C1—Ni1—O4	−178.5 (3)
C6—C7—C12—C11	−179.4 (4)	C2—C1—Ni1—O4	162 (2)
C8—C7—C12—C11	−0.1 (6)	O2—C1—Ni1—O4i	108.2 (2)
N2—C14—C15—C16	179.0 (3)	O4—C1—Ni1—O4i	−73.3 (2)
C19—C14—C15—C16	−0.5 (5)	C2—C1—Ni1—O4i	89 (2)
N2—C14—C15—N1	−0.7 (4)	O2—C1—Ni1—C1i	131.1 (2)
C19—C14—C15—N1	179.7 (3)	O4—C1—Ni1—C1i	−50.43 (17)
C14—C15—C16—C17	0.5 (5)	C2—C1—Ni1—C1i	112 (2)
N1—C15—C16—C17	−179.8 (3)	O4—C1—O2—Ni1	−1.6 (4)
C15—C16—C17—C18	−0.4 (6)	C2—C1—O2—Ni1	177.3 (3)
C16—C17—C18—C19	0.4 (7)	N1—Ni1—O2—C1	88.6 (2)
C17—C18—C19—C14	−0.4 (6)	N1i—Ni1—O2—C1	−170.7 (2)
N2—C14—C19—C18	−179.0 (4)	O2i—Ni1—O2—C1	−40.39 (19)
C15—C14—C19—C18	0.5 (6)	O4—Ni1—O2—C1	0.86 (19)
N2—C13—N1—C15	0.3 (4)	O4i—Ni1—O2—C1	−76.3 (2)
N2—C13—N1—Ni1	174.9 (2)	C1i—Ni1—O2—C1	−66.1 (3)
C16—C15—N1—C13	−179.5 (4)	O2—C1—O4—Ni1	1.4 (3)
C14—C15—N1—C13	0.3 (4)	C2—C1—O4—Ni1	−177.4 (3)
C16—C15—N1—Ni1	6.8 (6)	N1—Ni1—O4—C1	−101.9 (2)
C14—C15—N1—Ni1	−173.4 (2)	N1i—Ni1—O4—C1	17.0 (3)
N1—C13—N2—C14	−0.8 (4)	O2—Ni1—O4—C1	−0.86 (19)
C15—C14—N2—C13	0.9 (4)	O2i—Ni1—O4—C1	164.7 (2)
C19—C14—N2—C13	−179.5 (4)	O4i—Ni1—O4—C1	106.7 (2)
C13—N1—Ni1—N1i	109.3 (3)	C1i—Ni1—O4—C1	135.57 (19)
C15—N1—Ni1—N1i	−77.9 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4	0.90 (8)	2.24 (8)	2.988 (6)	141 (8)
N2—H2···O4ii	0.86	2.00	2.791 (4)	152

Symmetry code: (ii) −x+1, −y+1, −z+1.