{4,4'-Dimeth-oxy-2,2'-[1,1'-(ethane-1,2-diyldinitrilo)diethyl-idyne]diphenolato}nickel(II) hemihydrate.

In the title complex, [Ni(C(20)H(22)N(2)O(4))]·0.5H(2)O, the Ni(II) ion is in a slightly distorted square-planar geometry involving an N(2)O(2) atom set of the tetra-dentate Schiff base ligand. The asymmetric unit contains one mol-ecule of the complex and half a water solvent mol-ecule. The solvent water mol-ecule lies on a crystallographic twofold rotation axis. An inter-molecular O-H⋯O hydrogen bond forms an R(2) (1)(4) ring motif involving a bifurcated hydrogen bond to the phenolate O atoms of the complex. In the crystal structure, mol-ecules are linked by π-π stacking inter-actions, with centroid-centroid distances in the range 3.5310 (11)-3.7905 (12) Å, forming extended chains along the b axis. In addition, there are Ni⋯Ni and Ni⋯N inter-actions [3.4404 (4)-4.1588 (4) and 3.383 (2)-3.756 (2) Å, respectively] which are shorter than the sum of the van der Waals radii of the relevant atoms. Further stabilization of the crystal structure is attained by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures see, for example: Clark et al. (1968 ▶, 1969 ▶, 1970 ▶); Hodgson (1975 ▶). For applications and bioactivities see, for example: Elmali et al. (2000 ▶); Blower (1998 ▶); Granovski et al. (1993 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶); Fun & Kia (2008 ▶).

Experimental

Crystal data

[Ni(C20H22N2O4)]·0.5H2O

M = 422.11

Monoclinic,

a = 29.1721 (7) Å

b = 7.3032 (2) Å

c = 17.2833 (4) Å

β = 101.323 (1)°

V = 3610.53 (16) Å3

Z = 8

Mo Kα radiation

μ = 1.11 mm−1

T = 100.0 (1) K

0.33 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.712, T max = 0.853

21087 measured reflections

5319 independent reflections

4166 reflections with I > 2˘I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.138

S = 1.04

5319 reflections

253 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −0.90 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023362/lh2663sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023362/lh2663Isup2.hkl

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

[Ni(C20H22N2O4)]·0.5H2O	F000 = 1776
Mr = 422.11	Dx = 1.557 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6474 reflections
a = 29.1721 (7) Å	θ = 2.4–28.5º
b = 7.3032 (2) Å	µ = 1.11 mm−1
c = 17.2833 (4) Å	T = 100.0 (1) K
β = 101.323 (1)º	Block, red
V = 3610.53 (16) Å3	0.33 × 0.18 × 0.15 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	5319 independent reflections
Radiation source: fine-focus sealed tube	4166 reflections with I > 2˘I)
Monochromator: graphite	Rint = 0.042
T = 100.0(1) K	θmax = 30.2º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −35→41
Tmin = 0.712, Tmax = 0.853	k = −10→8
21087 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0817P)2 + 1.6212P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5319 reflections	Δρmax = 1.43 e Å−3
253 parameters	Δρmin = −0.90 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Ni1	0.013248 (10)	0.72441 (4)	0.025207 (15)	0.01283 (11)
O1	0.04524 (6)	0.6694 (2)	0.12462 (9)	0.0166 (3)
O2	−0.02834 (6)	0.8182 (2)	0.08056 (9)	0.0163 (3)
O3	0.22776 (6)	0.4706 (3)	0.23839 (11)	0.0386 (6)
O4	−0.20747 (6)	1.0823 (3)	−0.00397 (10)	0.0263 (4)
N1	0.05957 (7)	0.6362 (3)	−0.02489 (11)	0.0148 (4)
N2	−0.02394 (7)	0.7776 (3)	−0.07261 (11)	0.0138 (4)
C1	0.08918 (8)	0.6183 (3)	0.14511 (13)	0.0146 (4)
C2	0.10797 (8)	0.6091 (3)	0.22710 (13)	0.0174 (5)
H2A	0.0889	0.6372	0.2627	0.021*
C3	0.15355 (9)	0.5599 (4)	0.25526 (14)	0.0229 (5)
H3A	0.1651	0.5554	0.3094	0.027*
C4	0.18251 (9)	0.5167 (4)	0.20272 (14)	0.0221 (5)
C5	0.16555 (8)	0.5227 (3)	0.12301 (13)	0.0184 (5)
H5A	0.1852	0.4928	0.0885	0.022*
C6	0.11850 (8)	0.5736 (3)	0.09201 (13)	0.0148 (4)
C7	0.10115 (8)	0.5758 (3)	0.00639 (13)	0.0148 (5)
C8	0.04336 (8)	0.6242 (3)	−0.11176 (12)	0.0155 (5)
H8A	0.0355	0.4982	−0.1266	0.019*
H8B	0.0683	0.6625	−0.1379	0.019*
C9	0.00088 (9)	0.7449 (3)	−0.13816 (13)	0.0167 (5)
H9A	0.0106	0.8611	−0.1568	0.020*
H9B	−0.0202	0.6866	−0.1816	0.020*
C10	−0.06551 (8)	0.8514 (3)	−0.08899 (13)	0.0147 (4)
C11	−0.09141 (8)	0.8976 (3)	−0.02736 (13)	0.0150 (4)
C12	−0.13832 (8)	0.9617 (3)	−0.04730 (13)	0.0165 (5)
H12A	−0.1531	0.9677	−0.1001	0.020*
C13	−0.16223 (8)	1.0148 (3)	0.00996 (14)	0.0182 (5)
C14	−0.14041 (8)	1.0085 (3)	0.08966 (13)	0.0184 (5)
H14A	−0.1562	1.0488	0.1283	0.022*
C15	−0.09594 (8)	0.9432 (3)	0.11049 (13)	0.0161 (5)
H15A	−0.0819	0.9378	0.1636	0.019*
C16	−0.07050 (8)	0.8834 (3)	0.05342 (13)	0.0152 (5)
C17	0.26105 (9)	0.4494 (4)	0.19015 (16)	0.0292 (6)
H17A	0.2906	0.4159	0.2221	0.044*
H17B	0.2643	0.5626	0.1636	0.044*
H17C	0.2510	0.3552	0.1519	0.044*
C18	0.13369 (9)	0.5047 (3)	−0.04465 (14)	0.0185 (5)
H18A	0.1160	0.4753	−0.0961	0.028*
H18B	0.1493	0.3968	−0.0210	0.028*
H18C	0.1565	0.5968	−0.0493	0.028*
C19	−0.08767 (8)	0.8943 (3)	−0.17351 (13)	0.0187 (5)
H19A	−0.0638	0.9289	−0.2019	0.028*
H19B	−0.1095	0.9932	−0.1747	0.028*
H19C	−0.1038	0.7879	−0.1977	0.028*
C20	−0.23260 (9)	1.0747 (4)	−0.08316 (15)	0.0263 (6)
H20A	−0.2635	1.1232	−0.0858	0.039*
H20B	−0.2347	0.9498	−0.1009	0.039*
H20C	−0.2166	1.1459	−0.1163	0.039*
O1W	0.0000	0.8705 (3)	0.2500	0.0218 (5)
H1W1	−0.0017	0.8066	0.2094	0.033*

	U11	U22	U33	U12	U13	U23
Ni1	0.01457 (17)	0.01553 (18)	0.00876 (15)	0.00044 (11)	0.00319 (11)	−0.00026 (10)
O1	0.0164 (8)	0.0229 (9)	0.0106 (7)	0.0030 (7)	0.0031 (6)	−0.0001 (6)
O2	0.0169 (8)	0.0207 (9)	0.0114 (7)	0.0043 (7)	0.0026 (6)	−0.0012 (6)
O3	0.0139 (9)	0.0829 (18)	0.0188 (9)	0.0118 (10)	0.0030 (8)	0.0066 (10)
O4	0.0159 (9)	0.0410 (12)	0.0216 (9)	0.0080 (8)	0.0026 (7)	−0.0027 (8)
N1	0.0197 (10)	0.0146 (10)	0.0110 (8)	−0.0028 (8)	0.0055 (7)	−0.0004 (7)
N2	0.0176 (10)	0.0149 (9)	0.0095 (8)	−0.0008 (8)	0.0042 (7)	−0.0002 (7)
C1	0.0161 (11)	0.0139 (11)	0.0139 (10)	−0.0014 (9)	0.0029 (8)	0.0002 (8)
C2	0.0187 (12)	0.0222 (12)	0.0124 (10)	−0.0009 (9)	0.0058 (9)	−0.0007 (9)
C3	0.0200 (13)	0.0356 (15)	0.0121 (11)	−0.0034 (11)	0.0007 (9)	0.0027 (10)
C4	0.0146 (12)	0.0341 (15)	0.0173 (11)	0.0013 (11)	0.0022 (9)	0.0037 (10)
C5	0.0155 (12)	0.0249 (13)	0.0155 (11)	0.0008 (10)	0.0050 (9)	−0.0003 (9)
C6	0.0158 (11)	0.0154 (11)	0.0134 (10)	−0.0018 (9)	0.0034 (8)	−0.0002 (8)
C7	0.0184 (12)	0.0136 (11)	0.0135 (10)	−0.0024 (9)	0.0055 (9)	−0.0005 (8)
C8	0.0182 (11)	0.0178 (11)	0.0116 (10)	0.0007 (9)	0.0056 (8)	−0.0010 (8)
C9	0.0187 (12)	0.0212 (12)	0.0111 (10)	−0.0013 (9)	0.0050 (9)	0.0002 (8)
C10	0.0170 (11)	0.0141 (11)	0.0124 (10)	−0.0022 (9)	0.0012 (8)	0.0009 (8)
C11	0.0184 (12)	0.0128 (11)	0.0141 (10)	−0.0017 (9)	0.0042 (9)	−0.0004 (8)
C12	0.0165 (12)	0.0169 (12)	0.0145 (10)	−0.0004 (9)	−0.0009 (9)	0.0026 (8)
C13	0.0150 (11)	0.0212 (12)	0.0178 (11)	0.0033 (9)	0.0023 (9)	0.0011 (9)
C14	0.0193 (12)	0.0219 (13)	0.0154 (11)	0.0016 (10)	0.0073 (9)	−0.0011 (9)
C15	0.0186 (12)	0.0171 (11)	0.0126 (10)	−0.0002 (9)	0.0032 (9)	−0.0003 (8)
C16	0.0171 (11)	0.0125 (11)	0.0163 (10)	−0.0001 (9)	0.0039 (9)	−0.0001 (8)
C17	0.0186 (13)	0.0424 (17)	0.0284 (14)	0.0081 (12)	0.0089 (11)	0.0058 (12)
C18	0.0191 (12)	0.0210 (12)	0.0165 (11)	0.0026 (10)	0.0064 (9)	−0.0015 (9)
C19	0.0214 (12)	0.0215 (12)	0.0124 (10)	0.0021 (10)	0.0014 (9)	0.0013 (9)
C20	0.0183 (13)	0.0335 (15)	0.0246 (13)	0.0054 (11)	−0.0019 (10)	−0.0003 (11)
O1W	0.0307 (14)	0.0245 (14)	0.0100 (10)	0.000	0.0039 (10)	0.000

Ni1—O2	1.8201 (16)	C8—H8B	0.9700
Ni1—O1	1.8315 (15)	C9—H9A	0.9700
Ni1—N1	1.8575 (19)	C9—H9B	0.9700
Ni1—N2	1.8617 (19)	C10—C11	1.461 (3)
O1—C1	1.315 (3)	C10—C19	1.510 (3)
O2—C16	1.316 (3)	C11—C16	1.413 (3)
O3—C4	1.384 (3)	C11—C12	1.423 (3)
O3—C17	1.407 (3)	C12—C13	1.374 (3)
O4—C13	1.385 (3)	C12—H12A	0.9300
O4—C20	1.421 (3)	C13—C14	1.400 (3)
N1—C7	1.304 (3)	C14—C15	1.363 (3)
N1—C8	1.486 (3)	C14—H14A	0.9300
N2—C10	1.307 (3)	C15—C16	1.415 (3)
N2—C9	1.479 (3)	C15—H15A	0.9300
C1—C6	1.410 (3)	C17—H17A	0.9600
C1—C2	1.417 (3)	C17—H17B	0.9600
C2—C3	1.371 (3)	C17—H17C	0.9600
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.392 (3)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.370 (3)	C19—H19A	0.9600
C5—C6	1.422 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.467 (3)	C20—H20A	0.9600
C7—C18	1.509 (3)	C20—H20B	0.9600
C8—C9	1.516 (3)	C20—H20C	0.9600
C8—H8A	0.9700	O1W—H1W1	0.8359
Ni1···Ni1i	3.4404 (4)	Ni1···N2ii	3.728 (2)
Ni1···Ni1ii	4.1588 (4)	Cg1···Cg3iii	3.7905 (12)
Ni1···N1i	3.383 (2)	Cg3···Cg4iv	3.5310 (11)
Ni1···N2i	3.756 (2)	Cg4···Cg4iii	3.6152 (11)
O2—Ni1—O1	81.89 (7)	C8—C9—H9B	109.4
O2—Ni1—N1	175.30 (8)	H9A—C9—H9B	108.0
O1—Ni1—N1	94.47 (8)	N2—C10—C11	121.9 (2)
O2—Ni1—N2	93.96 (8)	N2—C10—C19	119.9 (2)
O1—Ni1—N2	175.13 (8)	C11—C10—C19	118.2 (2)
N1—Ni1—N2	89.81 (8)	C16—C11—C12	118.1 (2)
C1—O1—Ni1	127.23 (14)	C16—C11—C10	121.2 (2)
C16—O2—Ni1	128.42 (14)	C12—C11—C10	120.6 (2)
C4—O3—C17	118.2 (2)	C13—C12—C11	121.2 (2)
C13—O4—C20	116.57 (19)	C13—C12—H12A	119.4
C7—N1—C8	118.98 (19)	C11—C12—H12A	119.4
C7—N1—Ni1	128.81 (16)	C12—C13—O4	125.2 (2)
C8—N1—Ni1	112.03 (14)	C12—C13—C14	120.2 (2)
C10—N2—C9	118.29 (19)	O4—C13—C14	114.6 (2)
C10—N2—Ni1	129.30 (16)	C15—C14—C13	119.8 (2)
C9—N2—Ni1	112.11 (15)	C15—C14—H14A	120.1
O1—C1—C6	125.0 (2)	C13—C14—H14A	120.1
O1—C1—C2	116.6 (2)	C14—C15—C16	121.8 (2)
C6—C1—C2	118.4 (2)	C14—C15—H15A	119.1
C3—C2—C1	121.7 (2)	C16—C15—H15A	119.1
C3—C2—H2A	119.2	O2—C16—C11	124.8 (2)
C1—C2—H2A	119.2	O2—C16—C15	116.4 (2)
C2—C3—C4	119.9 (2)	C11—C16—C15	118.8 (2)
C2—C3—H3A	120.1	O3—C17—H17A	109.5
C4—C3—H3A	120.1	O3—C17—H17B	109.5
C5—C4—O3	125.5 (2)	H17A—C17—H17B	109.5
C5—C4—C3	120.2 (2)	O3—C17—H17C	109.5
O3—C4—C3	114.4 (2)	H17A—C17—H17C	109.5
C4—C5—C6	121.2 (2)	H17B—C17—H17C	109.5
C4—C5—H5A	119.4	C7—C18—H18A	109.5
C6—C5—H5A	119.4	C7—C18—H18B	109.5
C1—C6—C5	118.6 (2)	H18A—C18—H18B	109.5
C1—C6—C7	121.4 (2)	C7—C18—H18C	109.5
C5—C6—C7	119.9 (2)	H18A—C18—H18C	109.5
N1—C7—C6	122.0 (2)	H18B—C18—H18C	109.5
N1—C7—C18	121.0 (2)	C10—C19—H19A	109.5
C6—C7—C18	117.0 (2)	C10—C19—H19B	109.5
N1—C8—C9	110.42 (18)	H19A—C19—H19B	109.5
N1—C8—H8A	109.6	C10—C19—H19C	109.5
C9—C8—H8A	109.6	H19A—C19—H19C	109.5
N1—C8—H8B	109.6	H19B—C19—H19C	109.5
C9—C8—H8B	109.6	O4—C20—H20A	109.5
H8A—C8—H8B	108.1	O4—C20—H20B	109.5
N2—C9—C8	110.95 (18)	H20A—C20—H20B	109.5
N2—C9—H9A	109.4	O4—C20—H20C	109.5
C8—C9—H9A	109.4	H20A—C20—H20C	109.5
N2—C9—H9B	109.4	H20B—C20—H20C	109.5
O2—Ni1—O1—C1	−166.3 (2)	C8—N1—C7—C18	3.6 (3)
N1—Ni1—O1—C1	10.7 (2)	Ni1—N1—C7—C18	178.43 (16)
N2—Ni1—O1—C1	162.0 (9)	C1—C6—C7—N1	7.0 (3)
O1—Ni1—O2—C16	−172.8 (2)	C5—C6—C7—N1	−174.1 (2)
N1—Ni1—O2—C16	147.8 (9)	C1—C6—C7—C18	−173.1 (2)
N2—Ni1—O2—C16	4.6 (2)	C5—C6—C7—C18	5.8 (3)
O2—Ni1—N1—C7	33.3 (11)	C7—N1—C8—C9	−164.8 (2)
O1—Ni1—N1—C7	−5.7 (2)	Ni1—N1—C8—C9	19.5 (2)
N2—Ni1—N1—C7	176.6 (2)	C10—N2—C9—C8	−168.1 (2)
O2—Ni1—N1—C8	−151.6 (9)	Ni1—N2—C9—C8	17.5 (2)
O1—Ni1—N1—C8	169.41 (15)	N1—C8—C9—N2	−23.6 (3)
N2—Ni1—N1—C8	−8.25 (15)	C9—N2—C10—C11	−176.6 (2)
O2—Ni1—N2—C10	−1.8 (2)	Ni1—N2—C10—C11	−3.4 (3)
O1—Ni1—N2—C10	29.6 (10)	C9—N2—C10—C19	2.3 (3)
N1—Ni1—N2—C10	−179.0 (2)	Ni1—N2—C10—C19	175.59 (16)
O2—Ni1—N2—C9	171.73 (15)	N2—C10—C11—C16	7.2 (4)
O1—Ni1—N2—C9	−156.8 (9)	C19—C10—C11—C16	−171.8 (2)
N1—Ni1—N2—C9	−5.46 (16)	N2—C10—C11—C12	−174.0 (2)
Ni1—O1—C1—C6	−8.5 (3)	C19—C10—C11—C12	7.0 (3)
Ni1—O1—C1—C2	171.10 (16)	C16—C11—C12—C13	2.3 (3)
O1—C1—C2—C3	−179.1 (2)	C10—C11—C12—C13	−176.5 (2)
C6—C1—C2—C3	0.6 (4)	C11—C12—C13—O4	178.6 (2)
C1—C2—C3—C4	−0.3 (4)	C11—C12—C13—C14	0.7 (4)
C17—O3—C4—C5	8.2 (4)	C20—O4—C13—C12	7.9 (4)
C17—O3—C4—C3	−171.5 (2)	C20—O4—C13—C14	−174.1 (2)
C2—C3—C4—C5	−0.2 (4)	C12—C13—C14—C15	−2.4 (4)
C2—C3—C4—O3	179.5 (2)	O4—C13—C14—C15	179.5 (2)
O3—C4—C5—C6	−179.3 (3)	C13—C14—C15—C16	1.0 (4)
C3—C4—C5—C6	0.4 (4)	Ni1—O2—C16—C11	−2.0 (3)
O1—C1—C6—C5	179.2 (2)	Ni1—O2—C16—C15	178.21 (16)
C2—C1—C6—C5	−0.4 (3)	C12—C11—C16—O2	176.6 (2)
O1—C1—C6—C7	−1.9 (4)	C10—C11—C16—O2	−4.6 (4)
C2—C1—C6—C7	178.5 (2)	C12—C11—C16—C15	−3.7 (3)
C4—C5—C6—C1	−0.1 (4)	C10—C11—C16—C15	175.2 (2)
C4—C5—C6—C7	−179.0 (2)	C14—C15—C16—O2	−178.2 (2)
C8—N1—C7—C6	−176.5 (2)	C14—C15—C16—C11	2.1 (4)
Ni1—N1—C7—C6	−1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.84	2.41	3.1173 (19)	143
O1W—H1W1···O2	0.84	2.21	2.9077 (16)	141
C8—H8A···O2i	0.97	2.47	3.319 (3)	146
C9—H9A···O1Wii	0.97	2.52	3.407 (3)	152
C18—H18B···Cg1iv	0.96	2.71	3.385 (2)	127
C19—H19C···Cg2iv	0.96	2.81	3.652 (3)	146

Ni1—O2	1.8201 (16)
Ni1—O1	1.8315 (15)
Ni1—N1	1.8575 (19)
Ni1—N2	1.8617 (19)

Ni1⋯Ni1i	3.4404 (4)
Ni1⋯Ni1ii	4.1588 (4)
Ni1⋯N1i	3.383 (2)
Ni1⋯N2i	3.756 (2)
Ni1⋯N2ii	3.728 (2)
Cg1⋯Cg3iii	3.7905 (12)
Cg3⋯Cg4iv	3.5310 (11)
Cg4⋯Cg4iii	3.6152 (11)

O2—Ni1—O1	81.89 (7)
O2—Ni1—N1	175.30 (8)
O1—Ni1—N1	94.47 (8)
O2—Ni1—N2	93.96 (8)
O1—Ni1—N2	175.13 (8)
N1—Ni1—N2	89.81 (8)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg3, and Cg4 are the centroids of the C11–C16, Ni1-O1-C1-C6-C7-N1 and Ni1-O2-C16-C11-C10-N2 rings, respectively.

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1	0.84	2.41	3.1173 (19)	143
O1W—H1W1⋯O2	0.84	2.21	2.9077 (16)	141
C8—H8A⋯O2i	0.97	2.47	3.319 (3)	146
C9—H9A⋯O1Wii	0.97	2.52	3.407 (3)	152
C18—H18B⋯Cg1iv	0.96	2.71	3.385 (2)	127
C19—H19C⋯Cg2iv	0.96	2.81	3.652 (3)	146

Symmetry codes: (i) ; (ii) ; (iv) . Cg1 and Cg2 are centroids of the C11–C16 and C1–C6 benzene rings, respectively.