{4,4',5,5'-Tetra-methyl-2,2'-[1,1'-(ethane-1,2-diyldinitrilo)diethyl-idyne]diphenolato}nickel(II)-methanol-chloro-form (1/1/1).

In the title compound, [Ni(C(22)H(26)N(2)O(2))]·CH(3)OH·CHCl(3), 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 one mol-ecule each of chloro-form and methanol. The methanol mol-ecule is hydrogen bonded to the phenolate O atoms. In the crystal structure, short inter-molecular distances between the centroids of six-membered chelate rings [3.7002 (9) Å] indicate the presence of π-π inter-actions, which link the mol-ecules into stacks along the a axis. In addition, there are Ni⋯Ni distances which are shorter than the sum of the van der Waals radii of two Ni atoms. The crystal structure is further stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, and weak inter-molecular C-H⋯π inter-actions linking mol-ecules into extended one-dimensional chains along the c axis.

Related literature

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

Experimental

Crystal data

[Ni(C22H26N2O2)]·CH4O·CHCl3

M = 560.59

Triclinic,

a = 7.5473 (1) Å

b = 12.3899 (2) Å

c = 14.2481 (2) Å

α = 75.949 (1)°

β = 83.761 (1)°

γ = 74.693 (1)°

V = 1245.21 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.13 mm−1

T = 100.0 (1) K

0.36 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.684, T max = 0.882

29477 measured reflections

7348 independent reflections

5851 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.04

7348 reflections

305 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.80 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/S1600536808024306/lh2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024306/lh2659Isup2.hkl

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

[Ni(C22H26N2O2)]·CH4O·CHCl3	Z = 2
Mr = 560.59	F000 = 584
Triclinic, P1	Dx = 1.495 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5473 (1) Å	Cell parameters from 7819 reflections
b = 12.3899 (2) Å	θ = 2.5–29.3º
c = 14.2481 (2) Å	µ = 1.13 mm−1
α = 75.949 (1)º	T = 100.0 (1) K
β = 83.761 (1)º	Block, pink
γ = 74.693 (1)º	0.36 × 0.17 × 0.11 mm
V = 1245.21 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7348 independent reflections
Radiation source: fine-focus sealed tube	5851 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
T = 100.0(1) K	θmax = 30.2º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.684, Tmax = 0.882	k = −16→17
29477 measured reflections	l = −20→20

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.6625P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
7348 reflections	Δρmax = 0.71 e Å−3
305 parameters	Δρmin = −0.80 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	0.73830 (3)	0.02552 (2)	0.422240 (16)	0.01582 (7)
O1	0.59273 (18)	0.16632 (11)	0.43248 (9)	0.0194 (3)
O2	0.72158 (19)	0.08848 (11)	0.29250 (9)	0.0221 (3)
N1	0.7520 (2)	−0.03073 (13)	0.55493 (11)	0.0168 (3)
N2	0.8874 (2)	−0.11446 (13)	0.40463 (11)	0.0169 (3)
C1	0.5369 (2)	0.20434 (16)	0.51176 (13)	0.0173 (3)
C2	0.4308 (3)	0.31894 (16)	0.49954 (13)	0.0192 (4)
H2A	0.4036	0.3612	0.4371	0.023*
C3	0.3656 (3)	0.37099 (16)	0.57621 (14)	0.0198 (4)
C4	0.4074 (2)	0.30783 (17)	0.67159 (13)	0.0199 (4)
C5	0.5071 (2)	0.19556 (17)	0.68422 (13)	0.0195 (4)
H5A	0.5317	0.1539	0.7471	0.023*
C6	0.5749 (2)	0.13932 (16)	0.60716 (13)	0.0175 (3)
C7	0.6784 (2)	0.01988 (16)	0.62568 (13)	0.0179 (3)
C8	0.8448 (3)	−0.15402 (16)	0.58025 (13)	0.0194 (4)
H8A	0.7540	−0.1991	0.5959	0.023*
H8B	0.9172	−0.1700	0.6365	0.023*
C9	0.9685 (3)	−0.18622 (16)	0.49521 (13)	0.0193 (4)
H9A	1.0894	−0.1747	0.4995	0.023*
H9B	0.9822	−0.2666	0.4963	0.023*
C10	0.9362 (2)	−0.15019 (16)	0.32411 (13)	0.0176 (3)
C11	0.8610 (2)	−0.08203 (16)	0.23219 (13)	0.0175 (3)
C12	0.8869 (2)	−0.13058 (16)	0.14945 (13)	0.0187 (4)
H12A	0.9530	−0.2066	0.1556	0.022*
C14	0.7214 (2)	0.04489 (17)	0.05063 (13)	0.0187 (4)
C15	0.6937 (3)	0.09445 (16)	0.12986 (13)	0.0195 (4)
H15A	0.6291	0.1709	0.1224	0.023*
C16	0.7598 (3)	0.03323 (16)	0.22177 (13)	0.0185 (4)
C17	0.2529 (3)	0.49346 (17)	0.55849 (15)	0.0256 (4)
H17A	0.2465	0.5250	0.4900	0.038*
H17B	0.3094	0.5377	0.5873	0.038*
H17C	0.1311	0.4957	0.5869	0.038*
C18	0.3461 (3)	0.36271 (18)	0.75716 (14)	0.0263 (4)
H18A	0.3831	0.3070	0.8158	0.039*
H18B	0.2147	0.3904	0.7593	0.039*
H18C	0.4016	0.4257	0.7508	0.039*
C19	0.7027 (3)	−0.04867 (18)	0.72865 (14)	0.0252 (4)
H19A	0.6730	−0.1209	0.7348	0.038*
H19B	0.6226	−0.0067	0.7717	0.038*
H19C	0.8280	−0.0621	0.7449	0.038*
C20	1.0714 (3)	−0.26399 (16)	0.32619 (14)	0.0210 (4)
H20A	1.1643	−0.2748	0.3709	0.031*
H20B	1.1278	−0.2655	0.2626	0.031*
H20C	1.0084	−0.3244	0.3464	0.031*
C21	0.8500 (3)	−0.12856 (18)	−0.02354 (14)	0.0242 (4)
H21A	0.9156	−0.2074	−0.0029	0.036*
H21B	0.9204	−0.0900	−0.0746	0.036*
H21C	0.7333	−0.1251	−0.0467	0.036*
C22	0.6465 (3)	0.11405 (17)	−0.04537 (13)	0.0224 (4)
H22A	0.5839	0.1905	−0.0394	0.034*
H22B	0.5618	0.0786	−0.0646	0.034*
H22C	0.7458	0.1172	−0.0933	0.034*
Cl1	0.24264 (10)	0.37079 (6)	0.07683 (6)	0.05382 (19)
Cl2	0.28123 (13)	0.59955 (6)	0.06488 (7)	0.0640 (2)
C13	0.8193 (2)	−0.07080 (17)	0.06089 (13)	0.0197 (4)
Cl3	0.18264 (9)	0.46457 (7)	0.24800 (5)	0.05064 (18)
C23	0.3093 (3)	0.4605 (2)	0.13651 (18)	0.0350 (5)
H23A	0.4398	0.4293	0.1499	0.042*
O3	0.6398 (2)	0.33720 (14)	0.25019 (13)	0.0431 (4)
H1O3	0.6568	0.2655	0.2858	0.065*
C24	0.8172 (3)	0.3341 (2)	0.20835 (19)	0.0389 (5)
H24A	0.8137	0.4002	0.1561	0.058*
H24B	0.8625	0.2657	0.1839	0.058*
H24C	0.8971	0.3343	0.2563	0.058*

	U11	U22	U33	U12	U13	U23
Ni1	0.01784 (12)	0.01479 (12)	0.01401 (11)	−0.00247 (8)	−0.00203 (8)	−0.00282 (8)
O1	0.0229 (7)	0.0177 (6)	0.0157 (6)	−0.0012 (5)	−0.0018 (5)	−0.0041 (5)
O2	0.0332 (8)	0.0167 (7)	0.0146 (6)	−0.0019 (6)	−0.0026 (5)	−0.0038 (5)
N1	0.0164 (7)	0.0154 (7)	0.0180 (7)	−0.0030 (6)	−0.0023 (6)	−0.0030 (6)
N2	0.0164 (7)	0.0164 (7)	0.0171 (7)	−0.0036 (6)	−0.0023 (5)	−0.0019 (6)
C1	0.0160 (8)	0.0185 (9)	0.0183 (8)	−0.0049 (7)	−0.0010 (6)	−0.0050 (7)
C2	0.0204 (9)	0.0185 (9)	0.0178 (8)	−0.0042 (7)	−0.0025 (7)	−0.0022 (7)
C3	0.0179 (8)	0.0187 (9)	0.0231 (9)	−0.0053 (7)	−0.0001 (7)	−0.0051 (7)
C4	0.0172 (9)	0.0225 (9)	0.0205 (9)	−0.0041 (7)	0.0005 (7)	−0.0075 (7)
C5	0.0173 (8)	0.0230 (9)	0.0174 (8)	−0.0036 (7)	−0.0010 (6)	−0.0047 (7)
C6	0.0163 (8)	0.0184 (9)	0.0179 (8)	−0.0039 (7)	−0.0010 (6)	−0.0043 (7)
C7	0.0154 (8)	0.0203 (9)	0.0172 (8)	−0.0046 (7)	−0.0011 (6)	−0.0022 (7)
C8	0.0217 (9)	0.0168 (9)	0.0179 (8)	−0.0025 (7)	−0.0034 (7)	−0.0017 (7)
C9	0.0207 (9)	0.0181 (9)	0.0172 (8)	−0.0019 (7)	−0.0037 (7)	−0.0023 (7)
C10	0.0166 (8)	0.0176 (9)	0.0195 (8)	−0.0055 (7)	−0.0005 (6)	−0.0047 (7)
C11	0.0190 (9)	0.0177 (9)	0.0170 (8)	−0.0065 (7)	−0.0009 (6)	−0.0039 (7)
C12	0.0184 (9)	0.0181 (9)	0.0202 (9)	−0.0041 (7)	−0.0002 (7)	−0.0065 (7)
C14	0.0161 (8)	0.0227 (9)	0.0178 (8)	−0.0067 (7)	−0.0001 (6)	−0.0035 (7)
C15	0.0215 (9)	0.0177 (9)	0.0187 (8)	−0.0033 (7)	−0.0007 (7)	−0.0050 (7)
C16	0.0205 (9)	0.0187 (9)	0.0170 (8)	−0.0061 (7)	0.0006 (6)	−0.0046 (7)
C17	0.0286 (10)	0.0197 (10)	0.0259 (10)	−0.0024 (8)	0.0010 (8)	−0.0053 (8)
C18	0.0299 (11)	0.0255 (10)	0.0226 (9)	−0.0013 (8)	−0.0010 (8)	−0.0100 (8)
C19	0.0293 (10)	0.0242 (10)	0.0171 (9)	−0.0005 (8)	−0.0014 (7)	−0.0019 (7)
C20	0.0204 (9)	0.0182 (9)	0.0228 (9)	−0.0007 (7)	−0.0011 (7)	−0.0061 (7)
C21	0.0245 (10)	0.0292 (11)	0.0207 (9)	−0.0048 (8)	−0.0021 (7)	−0.0107 (8)
C22	0.0237 (9)	0.0260 (10)	0.0179 (9)	−0.0068 (8)	−0.0010 (7)	−0.0048 (7)
Cl1	0.0519 (4)	0.0516 (4)	0.0728 (5)	−0.0196 (3)	0.0068 (3)	−0.0386 (4)
Cl2	0.0768 (6)	0.0307 (4)	0.0800 (6)	−0.0115 (3)	−0.0152 (4)	−0.0009 (4)
C13	0.0176 (8)	0.0250 (10)	0.0189 (8)	−0.0074 (7)	0.0020 (7)	−0.0085 (7)
Cl3	0.0402 (4)	0.0571 (4)	0.0579 (4)	−0.0051 (3)	0.0034 (3)	−0.0290 (3)
C23	0.0320 (12)	0.0268 (11)	0.0483 (14)	−0.0049 (9)	−0.0056 (10)	−0.0131 (10)
O3	0.0401 (10)	0.0246 (8)	0.0521 (11)	−0.0019 (7)	−0.0001 (8)	0.0073 (7)
C24	0.0369 (13)	0.0270 (12)	0.0498 (15)	−0.0053 (10)	−0.0087 (11)	−0.0028 (11)

Ni1—O2	1.8276 (13)	C14—C15	1.383 (3)
Ni1—O1	1.8298 (13)	C14—C13	1.409 (3)
Ni1—N1	1.8534 (15)	C14—C22	1.506 (3)
Ni1—N2	1.8592 (16)	C15—C16	1.414 (3)
O1—C1	1.314 (2)	C15—H15A	0.9300
O2—C16	1.317 (2)	C17—H17A	0.9600
N1—C7	1.311 (2)	C17—H17B	0.9600
N1—C8	1.475 (2)	C17—H17C	0.9600
N2—C10	1.310 (2)	C18—H18A	0.9600
N2—C9	1.469 (2)	C18—H18B	0.9600
C1—C2	1.413 (3)	C18—H18C	0.9600
C1—C6	1.418 (2)	C19—H19A	0.9600
C2—C3	1.382 (3)	C19—H19B	0.9600
C2—H2A	0.9300	C19—H19C	0.9600
C3—C4	1.416 (3)	C20—H20A	0.9600
C3—C17	1.506 (3)	C20—H20B	0.9600
C4—C5	1.374 (3)	C20—H20C	0.9600
C4—C18	1.509 (3)	C21—C13	1.511 (3)
C5—C6	1.419 (3)	C21—H21A	0.9600
C5—H5A	0.9300	C21—H21B	0.9600
C6—C7	1.454 (3)	C21—H21C	0.9600
C7—C19	1.510 (2)	C22—H22A	0.9600
C8—C9	1.514 (3)	C22—H22B	0.9600
C8—H8A	0.9700	C22—H22C	0.9600
C8—H8B	0.9700	Cl1—C23	1.749 (2)
C9—H9A	0.9700	Cl2—C23	1.748 (3)
C9—H9B	0.9700	Cl3—C23	1.767 (3)
C10—C11	1.457 (3)	C23—H23A	0.9800
C10—C20	1.502 (3)	O3—C24	1.400 (3)
C11—C16	1.411 (3)	O3—H1O3	0.8931
C11—C12	1.422 (2)	C24—H24A	0.9600
C12—C13	1.374 (3)	C24—H24B	0.9600
C12—H12A	0.9300	C24—H24C	0.9600
Ni1···Ni1i	4.1276 (3)	Ni1···Ni1ii	4.5626 (3)
O2—Ni1—O1	82.98 (6)	C14—C15—C16	122.47 (18)
O2—Ni1—N1	177.05 (6)	C14—C15—H15A	118.8
O1—Ni1—N1	94.26 (6)	C16—C15—H15A	118.8
O2—Ni1—N2	93.94 (6)	O2—C16—C11	124.29 (16)
O1—Ni1—N2	176.90 (6)	O2—C16—C15	117.16 (17)
N1—Ni1—N2	88.82 (7)	C11—C16—C15	118.55 (17)
C1—O1—Ni1	127.77 (12)	C3—C17—H17A	109.5
C16—O2—Ni1	126.95 (12)	C3—C17—H17B	109.5
C7—N1—C8	117.97 (15)	H17A—C17—H17B	109.5
C7—N1—Ni1	129.48 (13)	C3—C17—H17C	109.5
C8—N1—Ni1	112.23 (11)	H17A—C17—H17C	109.5
C10—N2—C9	119.07 (16)	H17B—C17—H17C	109.5
C10—N2—Ni1	128.89 (13)	C4—C18—H18A	109.5
C9—N2—Ni1	111.81 (12)	C4—C18—H18B	109.5
O1—C1—C2	116.60 (16)	H18A—C18—H18B	109.5
O1—C1—C6	124.99 (17)	C4—C18—H18C	109.5
C2—C1—C6	118.41 (16)	H18A—C18—H18C	109.5
C3—C2—C1	122.95 (17)	H18B—C18—H18C	109.5
C3—C2—H2A	118.5	C7—C19—H19A	109.5
C1—C2—H2A	118.5	C7—C19—H19B	109.5
C2—C3—C4	119.06 (18)	H19A—C19—H19B	109.5
C2—C3—C17	120.45 (17)	C7—C19—H19C	109.5
C4—C3—C17	120.50 (17)	H19A—C19—H19C	109.5
C5—C4—C3	118.32 (17)	H19B—C19—H19C	109.5
C5—C4—C18	120.77 (17)	C10—C20—H20A	109.5
C3—C4—C18	120.90 (17)	C10—C20—H20B	109.5
C4—C5—C6	124.01 (17)	H20A—C20—H20B	109.5
C4—C5—H5A	118.0	C10—C20—H20C	109.5
C6—C5—H5A	118.0	H20A—C20—H20C	109.5
C1—C6—C5	117.21 (17)	H20B—C20—H20C	109.5
C1—C6—C7	121.60 (16)	C13—C21—H21A	109.5
C5—C6—C7	121.19 (16)	C13—C21—H21B	109.5
N1—C7—C6	121.70 (16)	H21A—C21—H21B	109.5
N1—C7—C19	118.56 (17)	C13—C21—H21C	109.5
C6—C7—C19	119.73 (16)	H21A—C21—H21C	109.5
N1—C8—C9	109.21 (15)	H21B—C21—H21C	109.5
N1—C8—H8A	109.8	C14—C22—H22A	109.5
C9—C8—H8A	109.8	C14—C22—H22B	109.5
N1—C8—H8B	109.8	H22A—C22—H22B	109.5
C9—C8—H8B	109.8	C14—C22—H22C	109.5
H8A—C8—H8B	108.3	H22A—C22—H22C	109.5
N2—C9—C8	109.27 (15)	H22B—C22—H22C	109.5
N2—C9—H9A	109.8	C12—C13—C14	118.70 (17)
C8—C9—H9A	109.8	C12—C13—C21	120.37 (18)
N2—C9—H9B	109.8	C14—C13—C21	120.92 (17)
C8—C9—H9B	109.8	Cl2—C23—Cl1	111.33 (14)
H9A—C9—H9B	108.3	Cl2—C23—Cl3	109.86 (13)
N2—C10—C11	121.32 (17)	Cl1—C23—Cl3	110.63 (13)
N2—C10—C20	119.63 (16)	Cl2—C23—H23A	108.3
C11—C10—C20	119.06 (16)	Cl1—C23—H23A	108.3
C16—C11—C12	117.64 (16)	Cl3—C23—H23A	108.3
C16—C11—C10	121.81 (16)	C24—O3—H1O3	100.3
C12—C11—C10	120.55 (17)	O3—C24—H24A	109.5
C13—C12—C11	123.29 (18)	O3—C24—H24B	109.5
C13—C12—H12A	118.4	H24A—C24—H24B	109.5
C11—C12—H12A	118.4	O3—C24—H24C	109.5
C15—C14—C13	119.34 (17)	H24A—C24—H24C	109.5
C15—C14—C22	120.14 (18)	H24B—C24—H24C	109.5
C13—C14—C22	120.52 (17)
O2—Ni1—O1—C1	−175.67 (15)	C5—C6—C7—N1	−175.42 (17)
N1—Ni1—O1—C1	3.28 (15)	C1—C6—C7—C19	−175.21 (17)
O1—Ni1—O2—C16	−163.17 (16)	C5—C6—C7—C19	4.6 (3)
N2—Ni1—O2—C16	17.21 (16)	C7—N1—C8—C9	−162.36 (16)
O1—Ni1—N1—C7	−0.21 (17)	Ni1—N1—C8—C9	23.57 (18)
N2—Ni1—N1—C7	179.36 (16)	C10—N2—C9—C8	−158.37 (16)
O1—Ni1—N1—C8	173.00 (12)	Ni1—N2—C9—C8	26.54 (18)
N2—Ni1—N1—C8	−7.43 (12)	N1—C8—C9—N2	−31.8 (2)
O2—Ni1—N2—C10	−6.81 (16)	C9—N2—C10—C11	−179.55 (15)
N1—Ni1—N2—C10	174.26 (16)	Ni1—N2—C10—C11	−5.4 (3)
O2—Ni1—N2—C9	167.68 (12)	C9—N2—C10—C20	0.9 (2)
N1—Ni1—N2—C9	−11.26 (12)	Ni1—N2—C10—C20	175.00 (12)
Ni1—O1—C1—C2	177.47 (12)	N2—C10—C11—C16	11.8 (3)
Ni1—O1—C1—C6	−2.7 (3)	C20—C10—C11—C16	−168.63 (16)
O1—C1—C2—C3	−178.80 (16)	N2—C10—C11—C12	−167.88 (16)
C6—C1—C2—C3	1.3 (3)	C20—C10—C11—C12	11.7 (2)
C1—C2—C3—C4	0.5 (3)	C16—C11—C12—C13	0.3 (3)
C1—C2—C3—C17	−179.93 (17)	C10—C11—C12—C13	179.94 (17)
C2—C3—C4—C5	−1.9 (3)	C13—C14—C15—C16	−0.1 (3)
C17—C3—C4—C5	178.57 (17)	C22—C14—C15—C16	179.49 (17)
C2—C3—C4—C18	177.35 (17)	Ni1—O2—C16—C11	−15.6 (3)
C17—C3—C4—C18	−2.2 (3)	Ni1—O2—C16—C15	164.22 (13)
C3—C4—C5—C6	1.5 (3)	C12—C11—C16—O2	178.46 (16)
C18—C4—C5—C6	−177.74 (17)	C10—C11—C16—O2	−1.2 (3)
O1—C1—C6—C5	178.44 (16)	C12—C11—C16—C15	−1.4 (3)
C2—C1—C6—C5	−1.7 (2)	C10—C11—C16—C15	178.98 (16)
O1—C1—C6—C7	−1.8 (3)	C14—C15—C16—O2	−178.51 (17)
C2—C1—C6—C7	178.11 (16)	C14—C15—C16—C11	1.3 (3)
C4—C5—C6—C1	0.3 (3)	C11—C12—C13—C14	0.9 (3)
C4—C5—C6—C7	−179.48 (17)	C11—C12—C13—C21	−179.10 (17)
C8—N1—C7—C6	−176.32 (15)	C15—C14—C13—C12	−1.0 (3)
Ni1—N1—C7—C6	−3.4 (3)	C22—C14—C13—C12	179.41 (16)
C8—N1—C7—C19	3.7 (2)	C15—C14—C13—C21	179.03 (17)
Ni1—N1—C7—C19	176.56 (13)	C22—C14—C13—C21	−0.6 (3)
C1—C6—C7—N1	4.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1	0.89	2.23	2.980 (2)	142
O3—H1O3···O2	0.89	2.10	2.901 (2)	149
C23—H23A···O3	0.98	2.10	2.974 (3)	148
C9—H9A···Cg1ii	0.97	2.47	3.404 (2)	162
C20—H20A···Cg2ii	0.96	2.94	3.801 (2)	150
C21—H21B···Cg3iii	0.96	2.82	3.691 (2)	152

Ni1—O2	1.8276 (13)
Ni1—O1	1.8298 (13)
Ni1—N1	1.8534 (15)
Ni1—N2	1.8592 (16)

Ni1⋯Ni1i	4.1276 (3)
Ni1⋯Ni1ii	4.5626 (3)

O2—Ni1—O1	82.98 (6)
O2—Ni1—N1	177.05 (6)
O1—Ni1—N1	94.26 (6)
O2—Ni1—N2	93.94 (6)
O1—Ni1—N2	176.90 (6)
N1—Ni1—N2	88.82 (7)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1	0.89	2.23	2.980 (2)	142
O3—H1O3⋯O2	0.89	2.10	2.901 (2)	149
C23—H23A⋯O3	0.98	2.10	2.974 (3)	148
C9—H9A⋯Cg1ii	0.97	2.47	3.404 (2)	162
C20—H20A⋯Cg2ii	0.96	2.94	3.801 (2)	150
C21—H21B⋯Cg3iii	0.96	2.82	3.691 (2)	152

Symmetry codes: (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids of the Ni1/O1/C1/C6/C7/N1, C1–C6, and C11–C16 rings, respectively.