{6,6'-Dieth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II) monohydrate.

In the title complex, [Ni(C(23)H(28)N(2)O(4))]·H(2)O, the Ni(II) ion is coordinated by the N(2)O(2) unit of the tetra-dentate Schiff base ligand in a slightly distorted planar geometry. The asymmetric unit of the title compound comprises one complex mol-ecule and a water mol-ecule of crystallization. The H atoms of the water mol-ecule make bifurcated inter-molecular hydrogen bonds with the O atoms of the phenolate and eth-oxy groups with R(1) (2)(5) and R(1) (2)(6) ring motifs, which may, in part, influence the mol-ecular configuration. The dihedral angle between the two benzene rings is 31.43 (5)°. The crystal structure is further stabilized by inter-molecular C-H⋯O and C-H⋯π inter-actions, which link neighbouring mol-ecules into one-dimensional extended chains along the a axis. An inter-esting feature of the crystal structure is the short inter-molecular C⋯C [3.3044 (14) Å] contact which is shorter than the sum of the van der Waals radii.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For related structures see, for example: Clark et al. (1968 ▶, 1969 ▶, 1970 ▶). For the applications and bioactivities of Schiff base complexes with transition metals, see, for example: Elmali et al. (2000 ▶); Blower (1998 ▶); Granovski et al., (1993 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Ni(C23H28N2O4)]·H2O

M = 473.20

Triclinic,

a = 9.3797 (1) Å

b = 10.7570 (1) Å

c = 12.8002 (1) Å

α = 65.811 (1)°

β = 68.87°

γ = 78.336 (1)°

V = 1096.64 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.92 mm−1

T = 100 K

0.36 × 0.19 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.733, T max = 0.879

29688 measured reflections

9211 independent reflections

8270 reflections with I > 2σI)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.04

9211 reflections

290 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008721/at2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008721/at2741Isup2.hkl

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

[Ni(C23H28N2O4)]·H2O	Z = 2
Mr = 473.20	F(000) = 500
Triclinic, P1	Dx = 1.433 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3797 (1) Å	Cell parameters from 9961 reflections
b = 10.7570 (1) Å	θ = 2.2–39.8°
c = 12.8002 (1) Å	µ = 0.92 mm−1
α = 65.811 (1)°	T = 100 K
β = 68.87°	Block, green
γ = 78.336 (1)°	0.36 × 0.19 × 0.14 mm
V = 1096.64 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8270 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2005)	θmax = 34.5°, θmin = 1.8°
Tmin = 0.733, Tmax = 0.879	h = −14→14
29688 measured reflections	k = −17→16
9211 independent reflections	l = −20→20

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.3434P] where P = (Fo2 + 2Fc2)/3
9211 reflections	(Δ/σ)max = 0.002
290 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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.

	x	y	z	Uiso*/Ueq
Ni1	0.226401 (12)	−0.053714 (11)	0.977253 (10)	0.01153 (3)
O1	0.23133 (8)	−0.03160 (7)	0.82469 (6)	0.01499 (11)
O2	0.29583 (8)	0.12152 (7)	0.90220 (6)	0.01433 (11)
O3	0.28411 (8)	0.03631 (7)	0.59447 (6)	0.01764 (12)
O4	0.30413 (8)	0.38398 (7)	0.78316 (6)	0.01683 (12)
N1	0.10045 (8)	−0.20138 (8)	1.05666 (7)	0.01348 (12)
N2	0.28140 (8)	−0.09129 (8)	1.11477 (7)	0.01317 (12)
C1	0.17327 (10)	−0.10785 (9)	0.79462 (8)	0.01354 (14)
C2	0.19469 (10)	−0.07175 (9)	0.66932 (8)	0.01518 (14)
C3	0.12695 (11)	−0.14175 (10)	0.63155 (9)	0.01851 (16)
H3A	0.1417	−0.1157	0.5481	0.022*
C4	0.03610 (12)	−0.25156 (11)	0.71655 (10)	0.02041 (17)
H4A	−0.0122	−0.2979	0.6905	0.024*
C5	0.01751 (11)	−0.29140 (10)	0.83686 (9)	0.01839 (16)
H5A	−0.0420	−0.3666	0.8936	0.022*
C6	0.08636 (10)	−0.22137 (9)	0.87752 (8)	0.01478 (14)
C7	0.05068 (10)	−0.25756 (9)	1.00486 (8)	0.01497 (14)
H7A	−0.0157	−0.3295	1.0562	0.018*
C8	0.02317 (10)	−0.23401 (9)	1.18710 (8)	0.01525 (15)
H8A	−0.0543	−0.3007	1.2157	0.018*
H8B	−0.0316	−0.1499	1.1996	0.018*
C9	0.13208 (10)	−0.29300 (9)	1.26399 (8)	0.01469 (14)
C10	0.29062 (10)	−0.23683 (9)	1.19059 (8)	0.01490 (14)
H10A	0.3476	−0.2494	1.2463	0.018*
H10B	0.3484	−0.2895	1.1387	0.018*
C11	0.33388 (10)	−0.00677 (9)	1.13864 (8)	0.01485 (14)
H11A	0.3686	−0.0425	1.2072	0.018*
C12	0.34334 (10)	0.13722 (9)	1.06889 (8)	0.01425 (14)
C13	0.38100 (12)	0.22038 (10)	1.11540 (9)	0.01869 (16)
H13A	0.4020	0.1802	1.1901	0.022*
C14	0.38748 (12)	0.35894 (10)	1.05349 (9)	0.01931 (17)
H14A	0.4100	0.4146	1.0864	0.023*
C15	0.36063 (11)	0.41821 (10)	0.94107 (9)	0.01667 (15)
H15A	0.3634	0.5142	0.8989	0.020*
C16	0.33023 (10)	0.33740 (9)	0.89181 (8)	0.01361 (14)
C17	0.32095 (9)	0.19304 (9)	0.95500 (8)	0.01256 (13)
C18	0.06211 (12)	−0.25176 (11)	1.37441 (9)	0.02151 (18)
H18A	0.0491	−0.1520	1.3479	0.032*
H18B	0.1303	−0.2864	1.4244	0.032*
H18C	−0.0378	−0.2906	1.4215	0.032*
C19	0.15271 (12)	−0.44884 (10)	1.30393 (11)	0.02356 (19)
H19A	0.2224	−0.4841	1.3527	0.035*
H19B	0.1958	−0.4741	1.2328	0.035*
H19C	0.0532	−0.4880	1.3519	0.035*
C20	0.29788 (12)	0.09025 (10)	0.46874 (8)	0.01952 (17)
H20A	0.1955	0.1167	0.4575	0.023*
H20B	0.3498	0.0213	0.4322	0.023*
C21	0.39176 (14)	0.21404 (11)	0.41110 (9)	0.02295 (19)
H21A	0.3962	0.2597	0.3263	0.034*
H21B	0.4957	0.1851	0.4164	0.034*
H21C	0.3440	0.2774	0.4533	0.034*
C22	0.35841 (11)	0.51438 (9)	0.69639 (9)	0.01766 (16)
H22A	0.4706	0.5140	0.6771	0.021*
H22B	0.3085	0.5873	0.7284	0.021*
C23	0.31822 (12)	0.53790 (11)	0.58548 (9)	0.02132 (18)
H23A	0.3592	0.6233	0.5216	0.032*
H23B	0.2066	0.5439	0.6047	0.032*
H23C	0.3627	0.4618	0.5580	0.032*
O1W	0.47217 (9)	0.17324 (9)	0.65560 (7)	0.02297 (15)
H2W1	0.422 (2)	0.1245 (18)	0.6513 (16)	0.037 (5)*
H1W1	0.419 (2)	0.187 (2)	0.7124 (19)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
Ni1	0.01281 (5)	0.01131 (5)	0.01095 (5)	−0.00182 (3)	−0.00487 (4)	−0.00308 (4)
O1	0.0199 (3)	0.0142 (3)	0.0134 (3)	−0.0042 (2)	−0.0070 (2)	−0.0047 (2)
O2	0.0197 (3)	0.0125 (3)	0.0130 (3)	−0.0036 (2)	−0.0068 (2)	−0.0040 (2)
O3	0.0247 (3)	0.0172 (3)	0.0125 (3)	−0.0044 (2)	−0.0076 (2)	−0.0040 (2)
O4	0.0215 (3)	0.0138 (3)	0.0151 (3)	−0.0060 (2)	−0.0086 (2)	−0.0004 (2)
N1	0.0123 (3)	0.0136 (3)	0.0136 (3)	−0.0012 (2)	−0.0045 (2)	−0.0036 (2)
N2	0.0133 (3)	0.0135 (3)	0.0122 (3)	−0.0014 (2)	−0.0051 (2)	−0.0031 (2)
C1	0.0141 (3)	0.0130 (3)	0.0159 (4)	0.0007 (3)	−0.0066 (3)	−0.0067 (3)
C2	0.0171 (4)	0.0149 (4)	0.0162 (4)	0.0001 (3)	−0.0071 (3)	−0.0071 (3)
C3	0.0209 (4)	0.0207 (4)	0.0199 (4)	−0.0005 (3)	−0.0089 (3)	−0.0114 (3)
C4	0.0200 (4)	0.0232 (4)	0.0258 (5)	−0.0024 (3)	−0.0084 (3)	−0.0148 (4)
C5	0.0160 (4)	0.0195 (4)	0.0229 (4)	−0.0038 (3)	−0.0045 (3)	−0.0110 (3)
C6	0.0133 (3)	0.0153 (4)	0.0174 (4)	−0.0015 (3)	−0.0045 (3)	−0.0076 (3)
C7	0.0125 (3)	0.0146 (4)	0.0174 (4)	−0.0020 (3)	−0.0043 (3)	−0.0052 (3)
C8	0.0115 (3)	0.0181 (4)	0.0134 (3)	−0.0008 (3)	−0.0033 (3)	−0.0037 (3)
C9	0.0132 (3)	0.0137 (3)	0.0136 (3)	−0.0005 (3)	−0.0043 (3)	−0.0017 (3)
C10	0.0132 (3)	0.0140 (3)	0.0154 (4)	0.0001 (3)	−0.0061 (3)	−0.0025 (3)
C11	0.0152 (3)	0.0172 (4)	0.0125 (3)	−0.0024 (3)	−0.0055 (3)	−0.0041 (3)
C12	0.0155 (3)	0.0164 (4)	0.0124 (3)	−0.0036 (3)	−0.0049 (3)	−0.0052 (3)
C13	0.0228 (4)	0.0221 (4)	0.0152 (4)	−0.0062 (3)	−0.0070 (3)	−0.0076 (3)
C14	0.0222 (4)	0.0212 (4)	0.0189 (4)	−0.0068 (3)	−0.0057 (3)	−0.0096 (3)
C15	0.0167 (4)	0.0163 (4)	0.0183 (4)	−0.0042 (3)	−0.0044 (3)	−0.0072 (3)
C16	0.0126 (3)	0.0145 (3)	0.0140 (3)	−0.0025 (3)	−0.0043 (3)	−0.0047 (3)
C17	0.0117 (3)	0.0138 (3)	0.0130 (3)	−0.0021 (2)	−0.0039 (3)	−0.0052 (3)
C18	0.0204 (4)	0.0266 (5)	0.0143 (4)	0.0003 (3)	−0.0051 (3)	−0.0056 (3)
C19	0.0205 (4)	0.0134 (4)	0.0302 (5)	−0.0011 (3)	−0.0082 (4)	−0.0014 (4)
C20	0.0286 (5)	0.0188 (4)	0.0137 (4)	−0.0003 (3)	−0.0089 (3)	−0.0069 (3)
C21	0.0347 (5)	0.0193 (4)	0.0141 (4)	−0.0035 (4)	−0.0074 (4)	−0.0048 (3)
C22	0.0174 (4)	0.0138 (4)	0.0185 (4)	−0.0039 (3)	−0.0065 (3)	−0.0006 (3)
C23	0.0216 (4)	0.0201 (4)	0.0175 (4)	−0.0021 (3)	−0.0070 (3)	−0.0013 (3)
O1W	0.0231 (3)	0.0296 (4)	0.0172 (3)	−0.0094 (3)	−0.0036 (3)	−0.0084 (3)

Ni1—O1	1.8523 (6)	C10—H10B	0.9900
Ni1—O2	1.8605 (6)	C11—C12	1.4385 (12)
Ni1—N2	1.8748 (7)	C11—H11A	0.9500
Ni1—N1	1.8766 (8)	C12—C17	1.4079 (12)
O1—C1	1.3068 (10)	C12—C13	1.4127 (12)
O2—C17	1.3109 (10)	C13—C14	1.3738 (14)
O3—C2	1.3692 (11)	C13—H13A	0.9500
O3—C20	1.4349 (11)	C14—C15	1.4089 (14)
O4—C16	1.3675 (11)	C14—H14A	0.9500
O4—C22	1.4370 (11)	C15—C16	1.3833 (12)
N1—C7	1.2994 (11)	C15—H15A	0.9500
N1—C8	1.4786 (12)	C16—C17	1.4310 (12)
N2—C11	1.2960 (11)	C18—H18A	0.9800
N2—C10	1.4700 (11)	C18—H18B	0.9800
C1—C6	1.4137 (12)	C18—H18C	0.9800
C1—C2	1.4327 (12)	C19—H19A	0.9800
C2—C3	1.3848 (12)	C19—H19B	0.9800
C3—C4	1.4109 (15)	C19—H19C	0.9800
C3—H3A	0.9500	C20—C21	1.5144 (15)
C4—C5	1.3716 (14)	C20—H20A	0.9900
C4—H4A	0.9500	C20—H20B	0.9900
C5—C6	1.4197 (13)	C21—H21A	0.9800
C5—H5A	0.9500	C21—H21B	0.9800
C6—C7	1.4352 (13)	C21—H21C	0.9800
C7—H7A	0.9500	C22—C23	1.5081 (14)
C8—C9	1.5382 (12)	C22—H22A	0.9900
C8—H8A	0.9900	C22—H22B	0.9900
C8—H8B	0.9900	C23—H23A	0.9800
C9—C19	1.5320 (13)	C23—H23B	0.9800
C9—C10	1.5330 (12)	C23—H23C	0.9800
C9—C18	1.5337 (14)	O1W—H2W1	0.798 (19)
C10—H10A	0.9900	O1W—H1W1	0.77 (2)
O1—Ni1—O2	84.55 (3)	C12—C11—H11A	117.6
O1—Ni1—N2	163.37 (3)	C17—C12—C13	120.81 (8)
O2—Ni1—N2	93.63 (3)	C17—C12—C11	120.71 (8)
O1—Ni1—N1	94.46 (3)	C13—C12—C11	118.45 (8)
O2—Ni1—N1	163.13 (3)	C14—C13—C12	120.52 (8)
N2—Ni1—N1	91.99 (3)	C14—C13—H13A	119.7
C1—O1—Ni1	128.09 (6)	C12—C13—H13A	119.7
C17—O2—Ni1	126.23 (6)	C13—C14—C15	119.80 (8)
C2—O3—C20	118.18 (7)	C13—C14—H14A	120.1
C16—O4—C22	117.93 (7)	C15—C14—H14A	120.1
C7—N1—C8	116.61 (7)	C16—C15—C14	120.37 (9)
C7—N1—Ni1	125.70 (6)	C16—C15—H15A	119.8
C8—N1—Ni1	116.04 (6)	C14—C15—H15A	119.8
C11—N2—C10	117.40 (7)	O4—C16—C15	125.18 (8)
C11—N2—Ni1	126.74 (6)	O4—C16—C17	113.82 (7)
C10—N2—Ni1	114.92 (6)	C15—C16—C17	120.99 (8)
O1—C1—C6	124.54 (8)	O2—C17—C12	124.49 (8)
O1—C1—C2	117.97 (8)	O2—C17—C16	118.10 (7)
C6—C1—C2	117.46 (8)	C12—C17—C16	117.39 (8)
O3—C2—C3	124.85 (8)	C9—C18—H18A	109.5
O3—C2—C1	114.03 (8)	C9—C18—H18B	109.5
C3—C2—C1	121.11 (9)	H18A—C18—H18B	109.5
C2—C3—C4	120.24 (9)	C9—C18—H18C	109.5
C2—C3—H3A	119.9	H18A—C18—H18C	109.5
C4—C3—H3A	119.9	H18B—C18—H18C	109.5
C5—C4—C3	120.01 (9)	C9—C19—H19A	109.5
C5—C4—H4A	120.0	C9—C19—H19B	109.5
C3—C4—H4A	120.0	H19A—C19—H19B	109.5
C4—C5—C6	120.67 (9)	C9—C19—H19C	109.5
C4—C5—H5A	119.7	H19A—C19—H19C	109.5
C6—C5—H5A	119.7	H19B—C19—H19C	109.5
C1—C6—C5	120.43 (8)	O3—C20—C21	106.38 (8)
C1—C6—C7	120.59 (8)	O3—C20—H20A	110.5
C5—C6—C7	118.55 (8)	C21—C20—H20A	110.5
N1—C7—C6	126.29 (8)	O3—C20—H20B	110.5
N1—C7—H7A	116.9	C21—C20—H20B	110.5
C6—C7—H7A	116.9	H20A—C20—H20B	108.6
N1—C8—C9	114.08 (7)	C20—C21—H21A	109.5
N1—C8—H8A	108.7	C20—C21—H21B	109.5
C9—C8—H8A	108.7	H21A—C21—H21B	109.5
N1—C8—H8B	108.7	C20—C21—H21C	109.5
C9—C8—H8B	108.7	H21A—C21—H21C	109.5
H8A—C8—H8B	107.6	H21B—C21—H21C	109.5
C19—C9—C10	107.48 (7)	O4—C22—C23	106.57 (8)
C19—C9—C18	110.13 (8)	O4—C22—H22A	110.4
C10—C9—C18	110.50 (8)	C23—C22—H22A	110.4
C19—C9—C8	110.92 (8)	O4—C22—H22B	110.4
C10—C9—C8	110.21 (7)	C23—C22—H22B	110.4
C18—C9—C8	107.62 (7)	H22A—C22—H22B	108.6
N2—C10—C9	112.31 (7)	C22—C23—H23A	109.5
N2—C10—H10A	109.1	C22—C23—H23B	109.5
C9—C10—H10A	109.1	H23A—C23—H23B	109.5
N2—C10—H10B	109.1	C22—C23—H23C	109.5
C9—C10—H10B	109.1	H23A—C23—H23C	109.5
H10A—C10—H10B	107.9	H23B—C23—H23C	109.5
N2—C11—C12	124.73 (8)	H2W1—O1W—H1W1	100.8 (18)
N2—C11—H11A	117.6
O2—Ni1—O1—C1	−168.23 (8)	Ni1—N1—C7—C6	2.41 (13)
N2—Ni1—O1—C1	107.35 (12)	C1—C6—C7—N1	−5.56 (14)
N1—Ni1—O1—C1	−5.14 (8)	C5—C6—C7—N1	−178.10 (9)
O1—Ni1—O2—C17	177.64 (7)	C7—N1—C8—C9	124.62 (9)
N2—Ni1—O2—C17	−18.95 (7)	Ni1—N1—C8—C9	−69.17 (9)
N1—Ni1—O2—C17	90.23 (12)	N1—C8—C9—C19	−89.00 (9)
O1—Ni1—N1—C7	2.24 (8)	N1—C8—C9—C10	29.91 (11)
O2—Ni1—N1—C7	88.17 (13)	N1—C8—C9—C18	150.47 (8)
N2—Ni1—N1—C7	−162.42 (8)	C11—N2—C10—C9	115.54 (9)
O1—Ni1—N1—C8	−162.55 (6)	Ni1—N2—C10—C9	−74.85 (8)
O2—Ni1—N1—C8	−76.61 (12)	C19—C9—C10—N2	161.00 (8)
N2—Ni1—N1—C8	32.80 (6)	C18—C9—C10—N2	−78.80 (9)
O1—Ni1—N2—C11	88.87 (13)	C8—C9—C10—N2	40.01 (10)
O2—Ni1—N2—C11	5.77 (8)	C10—N2—C11—C12	175.62 (8)
N1—Ni1—N2—C11	−158.31 (8)	Ni1—N2—C11—C12	7.39 (13)
O1—Ni1—N2—C10	−79.61 (12)	N2—C11—C12—C17	−11.73 (14)
O2—Ni1—N2—C10	−162.71 (6)	N2—C11—C12—C13	170.51 (9)
N1—Ni1—N2—C10	33.21 (6)	C17—C12—C13—C14	3.93 (14)
Ni1—O1—C1—C6	3.45 (13)	C11—C12—C13—C14	−178.31 (9)
Ni1—O1—C1—C2	−178.65 (6)	C12—C13—C14—C15	−1.80 (15)
C20—O3—C2—C3	6.21 (13)	C13—C14—C15—C16	−1.05 (15)
C20—O3—C2—C1	−172.95 (8)	C22—O4—C16—C15	21.08 (13)
O1—C1—C2—O3	3.97 (12)	C22—O4—C16—C17	−159.98 (8)
C6—C1—C2—O3	−177.98 (8)	C14—C15—C16—O4	−179.31 (8)
O1—C1—C2—C3	−175.22 (8)	C14—C15—C16—C17	1.82 (14)
C6—C1—C2—C3	2.83 (13)	Ni1—O2—C17—C12	19.68 (12)
O3—C2—C3—C4	−179.69 (9)	Ni1—O2—C17—C16	−161.96 (6)
C1—C2—C3—C4	−0.59 (14)	C13—C12—C17—O2	175.28 (9)
C2—C3—C4—C5	−1.52 (15)	C11—C12—C17—O2	−2.42 (13)
C3—C4—C5—C6	1.30 (15)	C13—C12—C17—C16	−3.09 (13)
O1—C1—C6—C5	174.88 (8)	C11—C12—C17—C16	179.21 (8)
C2—C1—C6—C5	−3.04 (13)	O4—C16—C17—O2	2.78 (11)
O1—C1—C6—C7	2.48 (14)	C15—C16—C17—O2	−178.23 (8)
C2—C1—C6—C7	−175.44 (8)	O4—C16—C17—C12	−178.75 (8)
C4—C5—C6—C1	1.04 (14)	C15—C16—C17—C12	0.25 (12)
C4—C5—C6—C7	173.59 (9)	C2—O3—C20—C21	175.61 (8)
C8—N1—C7—C6	167.12 (8)	C16—O4—C22—C23	178.53 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O1	0.80 (2)	2.499 (19)	3.0368 (12)	125.8 (16)
O1W—H2W1···O3	0.80 (2)	2.20 (2)	2.9805 (12)	164.7 (18)
O1W—H1W1···O2	0.77 (2)	2.15 (2)	2.8597 (10)	152 (2)
O1W—H1W1···O4	0.77 (2)	2.53 (2)	3.1658 (12)	140 (2)
C8—H8B···O1i	0.99	2.42	3.3216 (13)	151
C11—H11A···O1Wii	0.95	2.51	3.4242 (13)	161
C5—-H5A···Cg1i	0.95	2.88	3.3506 (12)	111
C10—-H10B···Cg1ii	0.99	2.73	3.4406 (11)	129
C22—-H22B···Cg2iii	0.99	2.87	3.8068 (11)	158

Table 1

Selected bond lengths (Å)

Ni1—O1	1.8523 (6)
Ni1—O2	1.8605 (6)
Ni1—N2	1.8748 (7)
Ni1—N1	1.8766 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O1	0.80 (2)	2.499 (19)	3.0368 (12)	125.8 (16)
O1W—H2W1⋯O3	0.80 (2)	2.20 (2)	2.9805 (12)	164.7 (18)
O1W—H1W1⋯O2	0.77 (2)	2.15 (2)	2.8597 (10)	152 (2)
O1W—H1W1⋯O4	0.77 (2)	2.53 (2)	3.1658 (12)	140 (2)
C8—H8B⋯O1i	0.99	2.42	3.3216 (13)	151
C11—H11A⋯O1Wii	0.95	2.51	3.4242 (13)	161
C5—-H5A⋯Cg1i	0.95	2.88	3.3506 (12)	111
C10—-H10B⋯Cg1ii	0.99	2.73	3.4406 (11)	129
C22—-H22B⋯Cg2iii	0.99	2.87	3.8068 (11)	158

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C12–C17 and C1–C6 benzene rings, respectively.