{μ-6,6'-Dieth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato}trinitratoholmium(III)nickel(II).

In the title heteronuclear Ni(II)-Ho(III) complex (systematic name: {μ-6,6'-dieth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolato-1κ(4)O(1),O(1'),O(6),O(6'):2κ(4)O(1),N,N',O(1')}trinitrato-1κ(6)O,O'-holmium(III)nickel(II)), [HoNi(C(20)H(22)N(2)O(4))(NO(3))(3)], with the hexa-dentate Schiff base compartmental ligand N,N'-bis-(3-ethoxy-salicyl-idene)ethyl-enediamine (H(2)L), the Ho and Ni atoms are doubly bridged by two phenolate O atoms of the Schiff base ligand. The coordination of Ni is square-planar with the donor centers of two imine N atoms and two phenolate O atoms. The holmium(III) center has a tenfold -coordination environment of O atoms, involving the phenolate O atoms, two eth-oxy O atoms and two O atoms each from the three nitrates. Weak C-H⋯O and O⋯Ni [3.383 (4) Å] inter-actions generate a two-dimensional zigzag sheet.

Related literature

For related literature, see: Baggio et al. (2000 ▶); Caravan et al. (1999 ▶); Edder et al. (2000 ▶); Knoer et al. (2005 ▶); Sui et al. (2006 ▶).

Experimental

Crystal data

[HoNi(C20H22N2O4)(NO3)3]

M = 764.07

Orthorhombic,

a = 8.5825 (8) Å

b = 13.7028 (14) Å

c = 21.203 (2) Å

V = 2493.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.98 mm−1

T = 293 (2) K

0.17 × 0.16 × 0.13 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.559, T max = 0.625

18705 measured reflections

5970 independent reflections

4299 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.113

S = 1.04

5970 reflections

364 parameters

H-atom parameters constrained

Δρmax = 2.00 e Å−3

Δρmin = −0.61 e Å−3

Absolute structure: Flack (1983 ▶), 2455 Friedel pairs

Flack parameter: −0.003 (18)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013755/hg2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013755/hg2401Isup2.hkl

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

[HoNi(C20H22N2O4)(NO3)3]	F000 = 1504
Mr = 764.07	Dx = 2.035 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6504 reflections
a = 8.5825 (8) Å	θ = 1.9–28.3º
b = 13.7028 (14) Å	µ = 3.98 mm−1
c = 21.203 (2) Å	T = 293 (2) K
V = 2493.6 (4) Å3	Block, red
Z = 4	0.17 × 0.16 × 0.13 mm

Bruker APEXII area-detector diffractometer	5970 independent reflections
Radiation source: fine-focus sealed tube	4299 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.055
T = 293(2) K	θmax = 28.3º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.559, Tmax = 0.626	k = −17→18
18705 measured reflections	l = −27→27

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043	(Δ/σ)max = 0.001
wR(F2) = 0.113	Δρmax = 2.00 e Å−3
S = 1.04	Δρmin = −0.61 e Å−3
5970 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
364 parameters	Extinction coefficient: 0.0058 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2455 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.003 (18)
Hydrogen site location: inferred from neighbouring sites

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
C5	−0.1509 (7)	0.3317 (5)	0.3044 (3)	0.0427 (15)
Ho1	0.25263 (3)	0.49982 (2)	0.400886 (12)	0.04143 (11)
Ni1	−0.06665 (9)	0.56000 (6)	0.31450 (4)	0.03838 (19)
O2	0.0323 (4)	0.4496 (3)	0.34434 (19)	0.0399 (10)
O1	0.0808 (5)	0.6237 (3)	0.36270 (19)	0.0411 (10)
N1	−0.1998 (6)	0.4934 (4)	0.2621 (2)	0.0434 (12)
N2	−0.1729 (6)	0.6703 (4)	0.2905 (3)	0.0423 (13)
N3	0.1352 (8)	0.5100 (5)	0.5279 (3)	0.0588 (16)
O6	0.0496 (6)	0.5277 (4)	0.4813 (2)	0.0647 (14)
C12	−0.1460 (7)	0.7577 (5)	0.3087 (3)	0.0470 (16)
H12	−0.2126	0.8065	0.2945	0.056*
O3	0.1551 (5)	0.3283 (3)	0.4234 (2)	0.0422 (10)
C18	0.0875 (7)	0.7189 (4)	0.3736 (3)	0.0386 (13)
O4	0.3135 (5)	0.6799 (3)	0.4295 (2)	0.0473 (11)
O5	0.2787 (6)	0.4948 (4)	0.5150 (2)	0.0609 (13)
C15	0.1149 (8)	0.9161 (5)	0.4034 (4)	0.0556 (18)
H15	0.1222	0.9816	0.4147	0.067*
C4	−0.0255 (7)	0.3594 (4)	0.3442 (3)	0.0387 (14)
O7	0.0834 (8)	0.5055 (4)	0.5815 (3)	0.0841 (17)
C19	0.4500 (8)	0.7097 (5)	0.4648 (3)	0.0533 (17)
H19A	0.4917	0.6538	0.4872	0.064*
H19B	0.4203	0.7583	0.4957	0.064*
C1	0.3381 (9)	0.1918 (6)	0.4400 (4)	0.059 (2)
H1A	0.2848	0.1544	0.4084	0.089*
H1B	0.3793	0.1487	0.4716	0.089*
H1C	0.4219	0.2275	0.4208	0.089*
C17	0.2135 (7)	0.7529 (4)	0.4098 (3)	0.0422 (15)
C13	−0.0195 (8)	0.7860 (4)	0.3498 (3)	0.0434 (15)
C14	−0.0046 (9)	0.8868 (5)	0.3667 (3)	0.0515 (17)
H14	−0.0773	0.9320	0.3524	0.062*
C2	0.2241 (8)	0.2632 (5)	0.4706 (3)	0.0487 (16)
H2A	0.1421	0.2270	0.4917	0.058*
H2B	0.2784	0.3017	0.5021	0.058*
O9	0.3184 (6)	0.5422 (4)	0.2897 (2)	0.0581 (13)
N4	0.3530 (6)	0.4577 (5)	0.2744 (3)	0.0517 (16)
O8	0.3482 (6)	0.3918 (3)	0.3167 (3)	0.0573 (12)
C9	−0.2254 (8)	0.3989 (5)	0.2623 (3)	0.0447 (15)
H9	−0.2964	0.3741	0.2333	0.054*
O12	0.5289 (6)	0.5328 (4)	0.3902 (3)	0.0593 (13)
N5	0.5831 (8)	0.4621 (5)	0.4212 (3)	0.0605 (16)
C16	0.2267 (9)	0.8516 (5)	0.4248 (3)	0.0510 (17)
H16	0.3099	0.8738	0.4489	0.061*
C6	−0.2073 (8)	0.2359 (5)	0.3070 (3)	0.0506 (17)
H6	−0.2863	0.2162	0.2798	0.061*
C3	0.0358 (7)	0.2907 (5)	0.3862 (3)	0.0417 (14)
C11	−0.3100 (8)	0.6507 (5)	0.2514 (3)	0.0516 (17)
H11A	−0.3272	0.7036	0.2218	0.062*
H11B	−0.4022	0.6434	0.2774	0.062*
C10	−0.2754 (8)	0.5578 (5)	0.2171 (3)	0.0513 (16)
H10A	−0.3710	0.5285	0.2016	0.062*
H10B	−0.2073	0.5702	0.1815	0.062*
O11	0.4839 (6)	0.4045 (4)	0.4421 (3)	0.0728 (17)
C20	0.5726 (10)	0.7506 (6)	0.4231 (4)	0.071 (2)
H20A	0.6009	0.7031	0.3919	0.106*
H20B	0.6624	0.7672	0.4478	0.106*
H20C	0.5336	0.8081	0.4026	0.106*
C8	−0.0229 (7)	0.1970 (5)	0.3887 (4)	0.0484 (16)
H8	0.0192	0.1514	0.4164	0.058*
O10	0.3939 (7)	0.4348 (5)	0.2204 (2)	0.0808 (18)
O13	0.7234 (6)	0.4536 (7)	0.4307 (3)	0.099 (2)
C7	−0.1465 (9)	0.1717 (5)	0.3492 (3)	0.0563 (19)
H7	−0.1884	0.1092	0.3518	0.068*

	U11	U22	U33	U12	U13	U23
C5	0.040 (3)	0.041 (3)	0.048 (4)	−0.006 (3)	−0.003 (3)	−0.002 (3)
Ho1	0.04247 (16)	0.03543 (16)	0.04639 (17)	−0.00007 (18)	−0.00389 (12)	0.00217 (13)
Ni1	0.0375 (4)	0.0340 (4)	0.0436 (4)	−0.0005 (3)	−0.0050 (4)	0.0047 (4)
O2	0.038 (2)	0.033 (2)	0.049 (2)	−0.0065 (18)	−0.0099 (18)	0.004 (2)
O1	0.045 (2)	0.026 (2)	0.052 (2)	0.0024 (19)	−0.014 (2)	0.004 (2)
N1	0.037 (2)	0.051 (3)	0.043 (3)	−0.005 (3)	−0.002 (2)	0.002 (3)
N2	0.040 (3)	0.038 (3)	0.049 (3)	−0.001 (2)	0.001 (2)	0.010 (3)
N3	0.085 (5)	0.037 (3)	0.054 (3)	0.003 (3)	0.007 (3)	−0.005 (3)
O6	0.066 (3)	0.076 (4)	0.052 (3)	0.003 (3)	−0.001 (3)	−0.001 (3)
C12	0.041 (3)	0.046 (4)	0.054 (4)	0.011 (3)	0.009 (3)	0.018 (4)
O3	0.045 (2)	0.027 (2)	0.054 (3)	−0.0026 (19)	−0.004 (2)	0.008 (2)
C18	0.039 (3)	0.034 (3)	0.043 (3)	−0.002 (3)	0.000 (3)	0.006 (3)
O4	0.049 (2)	0.037 (2)	0.056 (3)	−0.004 (2)	−0.016 (2)	0.000 (2)
O5	0.070 (3)	0.061 (3)	0.051 (3)	0.005 (3)	−0.008 (2)	0.002 (3)
C15	0.063 (4)	0.034 (4)	0.069 (5)	−0.007 (3)	0.008 (4)	0.003 (4)
C4	0.041 (3)	0.036 (3)	0.039 (3)	−0.004 (3)	0.001 (3)	−0.001 (3)
O7	0.120 (5)	0.077 (4)	0.055 (3)	0.004 (4)	0.013 (4)	0.003 (3)
C19	0.048 (4)	0.052 (4)	0.060 (4)	−0.002 (3)	−0.010 (4)	−0.006 (3)
C1	0.057 (4)	0.044 (4)	0.077 (5)	0.010 (3)	−0.016 (4)	−0.002 (4)
C17	0.053 (4)	0.031 (3)	0.043 (3)	0.004 (3)	0.010 (3)	0.003 (3)
C13	0.052 (4)	0.032 (3)	0.046 (3)	0.001 (3)	0.005 (3)	0.004 (3)
C14	0.061 (4)	0.032 (3)	0.062 (4)	0.011 (3)	0.001 (3)	0.008 (3)
C2	0.061 (4)	0.042 (4)	0.043 (3)	0.002 (3)	−0.010 (3)	0.008 (3)
O9	0.069 (3)	0.051 (3)	0.055 (3)	0.002 (3)	−0.004 (3)	0.012 (3)
N4	0.043 (3)	0.063 (4)	0.049 (3)	−0.018 (3)	−0.006 (3)	−0.003 (3)
O8	0.064 (3)	0.051 (3)	0.056 (3)	−0.007 (2)	0.001 (3)	−0.009 (3)
C9	0.047 (4)	0.041 (3)	0.046 (3)	−0.006 (3)	−0.003 (3)	0.000 (3)
O12	0.053 (3)	0.052 (3)	0.073 (3)	0.000 (2)	0.000 (3)	0.005 (3)
N5	0.055 (4)	0.068 (4)	0.059 (3)	−0.002 (3)	0.002 (3)	0.000 (3)
C16	0.054 (4)	0.047 (4)	0.053 (3)	−0.011 (3)	0.005 (3)	−0.001 (3)
C6	0.047 (4)	0.041 (4)	0.064 (4)	−0.006 (3)	0.002 (4)	−0.007 (4)
C3	0.042 (3)	0.034 (3)	0.049 (3)	−0.001 (3)	0.001 (3)	0.001 (3)
C11	0.046 (4)	0.056 (5)	0.053 (4)	0.005 (3)	−0.008 (3)	0.011 (4)
C10	0.049 (4)	0.051 (4)	0.054 (3)	−0.007 (3)	−0.019 (3)	0.004 (3)
O11	0.054 (3)	0.081 (4)	0.083 (4)	0.005 (3)	−0.003 (3)	0.029 (3)
C20	0.066 (5)	0.058 (5)	0.087 (5)	−0.016 (5)	0.006 (5)	−0.012 (5)
C8	0.047 (4)	0.034 (4)	0.064 (4)	0.001 (3)	0.005 (3)	0.008 (3)
O10	0.080 (4)	0.115 (5)	0.048 (3)	−0.034 (4)	0.013 (3)	−0.018 (4)
O13	0.044 (3)	0.138 (6)	0.114 (5)	0.010 (4)	−0.012 (3)	0.022 (5)
C7	0.063 (4)	0.034 (4)	0.072 (5)	−0.013 (3)	0.000 (4)	−0.002 (4)

Ho1—O1	2.390 (4)	C15—H15	0.9300
Ho1—O2	2.343 (4)	C4—C3	1.398 (9)
Ho1—O3	2.540 (4)	C19—C20	1.484 (10)
Ho1—O4	2.594 (4)	C19—H19A	0.9700
Ho1—O5	2.430 (5)	C19—H19B	0.9700
Ho1—O6	2.468 (5)	C1—C2	1.529 (10)
Ho1—O8	2.460 (5)	C1—H1A	0.9600
Ho1—O9	2.492 (5)	C1—H1B	0.9600
Ho1—O11	2.531 (5)	C1—H1C	0.9600
Ho1—O12	2.425 (5)	C17—C16	1.394 (9)
Ni1—O1	1.846 (4)	C13—C14	1.433 (9)
Ni1—O2	1.847 (4)	C14—H14	0.9300
Ni1—N1	1.837 (5)	C2—H2A	0.9700
Ni1—N2	1.837 (5)	C2—H2B	0.9700
C5—C6	1.400 (9)	O9—N4	1.239 (8)
C5—C4	1.419 (8)	N4—O10	1.238 (7)
C5—C9	1.433 (9)	N4—O8	1.272 (8)
O2—C4	1.332 (7)	C9—H9	0.9300
O1—C18	1.327 (7)	O12—N5	1.259 (8)
N1—C9	1.313 (8)	N5—O13	1.227 (8)
N1—C10	1.453 (8)	N5—O11	1.242 (8)
N2—C12	1.280 (8)	C16—H16	0.9300
N2—C11	1.465 (9)	C6—C7	1.359 (10)
N3—O7	1.221 (7)	C6—H6	0.9300
N3—O6	1.255 (8)	C3—C8	1.380 (9)
N3—O5	1.279 (8)	C11—C10	1.496 (10)
C12—C13	1.445 (9)	C11—H11A	0.9700
C12—H12	0.9300	C11—H11B	0.9700
O3—C3	1.392 (7)	C10—H10A	0.9700
O3—C2	1.466 (7)	C10—H10B	0.9700
C18—C13	1.393 (8)	C20—H20A	0.9600
C18—C17	1.406 (9)	C20—H20B	0.9600
O4—C17	1.383 (7)	C20—H20C	0.9600
O4—C19	1.449 (8)	C8—C7	1.396 (10)
C15—C14	1.348 (10)	C8—H8	0.9300
C15—C16	1.382 (10)	C7—H7	0.9300
C6—C5—C4	119.3 (6)	C19—O4—Ho1	123.5 (4)
C6—C5—C9	118.2 (6)	N3—O5—Ho1	96.9 (4)
C4—C5—C9	122.4 (6)	C14—C15—C16	121.8 (6)
O2—Ho1—O1	62.44 (14)	C14—C15—H15	119.1
O2—Ho1—O12	142.78 (15)	C16—C15—H15	119.1
O1—Ho1—O12	116.07 (17)	O2—C4—C3	118.9 (5)
O2—Ho1—O5	125.12 (15)	O2—C4—C5	122.1 (6)
O1—Ho1—O5	114.48 (17)	C3—C4—C5	118.9 (5)
O12—Ho1—O5	90.49 (18)	O4—C19—C20	111.9 (6)
O2—Ho1—O8	73.78 (15)	O4—C19—H19A	109.2
O1—Ho1—O8	112.76 (15)	C20—C19—H19A	109.2
O12—Ho1—O8	73.62 (17)	O4—C19—H19B	109.2
O5—Ho1—O8	132.44 (19)	C20—C19—H19B	109.2
O2—Ho1—O6	80.15 (16)	H19A—C19—H19B	107.9
O1—Ho1—O6	71.83 (16)	C2—C1—H1A	109.5
O12—Ho1—O6	136.61 (17)	C2—C1—H1B	109.5
O5—Ho1—O6	51.82 (17)	H1A—C1—H1B	109.5
O8—Ho1—O6	146.11 (17)	C2—C1—H1C	109.5
O2—Ho1—O9	76.56 (16)	H1A—C1—H1C	109.5
O1—Ho1—O9	69.75 (16)	H1B—C1—H1C	109.5
O12—Ho1—O9	69.29 (18)	O4—C17—C16	125.6 (6)
O5—Ho1—O9	157.98 (18)	O4—C17—C18	113.8 (5)
O8—Ho1—O9	51.54 (17)	C16—C17—C18	120.6 (6)
O6—Ho1—O9	141.01 (17)	C18—C13—C14	119.1 (6)
O2—Ho1—O11	131.15 (18)	C18—C13—C12	122.4 (6)
O1—Ho1—O11	165.27 (17)	C14—C13—C12	118.5 (6)
O12—Ho1—O11	50.32 (17)	C15—C14—C13	119.9 (6)
O5—Ho1—O11	64.50 (19)	C15—C14—H14	120.0
O8—Ho1—O11	71.28 (19)	C13—C14—H14	120.0
O6—Ho1—O11	113.28 (17)	O3—C2—C1	111.0 (5)
O9—Ho1—O11	105.60 (18)	O3—C2—H2A	109.4
O2—Ho1—O3	63.79 (14)	C1—C2—H2A	109.4
O1—Ho1—O3	121.17 (14)	O3—C2—H2B	109.4
O12—Ho1—O3	120.80 (16)	C1—C2—H2B	109.4
O5—Ho1—O3	79.44 (17)	H2A—C2—H2B	108.0
O8—Ho1—O3	71.93 (16)	N4—O9—Ho1	94.8 (4)
O6—Ho1—O3	77.33 (17)	O10—N4—O9	123.1 (7)
O9—Ho1—O3	117.91 (17)	O10—N4—O8	118.8 (7)
O11—Ho1—O3	73.51 (16)	O9—N4—O8	118.1 (6)
O2—Ho1—O4	124.19 (15)	N4—O8—Ho1	95.5 (4)
O1—Ho1—O4	61.83 (14)	N1—C9—C5	124.2 (6)
O12—Ho1—O4	69.37 (16)	N1—C9—H9	117.9
O5—Ho1—O4	77.05 (16)	C5—C9—H9	117.9
O8—Ho1—O4	132.43 (16)	N5—O12—Ho1	99.7 (4)
O6—Ho1—O4	80.41 (17)	O13—N5—O11	123.6 (8)
O9—Ho1—O4	87.35 (17)	O13—N5—O12	121.4 (7)
O11—Ho1—O4	104.59 (17)	O11—N5—O12	114.9 (6)
O3—Ho1—O4	154.49 (18)	C15—C16—C17	119.3 (7)
N1—Ni1—N2	86.1 (3)	C15—C16—H16	120.3
N1—Ni1—O1	175.1 (2)	C17—C16—H16	120.3
N2—Ni1—O1	96.0 (2)	C7—C6—C5	120.0 (6)
N1—Ni1—O2	94.9 (2)	C7—C6—H6	120.0
N2—Ni1—O2	175.7 (2)	C5—C6—H6	120.0
O1—Ni1—O2	83.27 (17)	C8—C3—O3	126.2 (6)
C4—O2—Ni1	126.1 (4)	C8—C3—C4	120.9 (6)
C4—O2—Ho1	125.1 (4)	O3—C3—C4	112.9 (5)
Ni1—O2—Ho1	107.79 (18)	N2—C11—C10	105.8 (5)
C18—O1—Ni1	126.2 (4)	N2—C11—H11A	110.6
C18—O1—Ho1	127.8 (4)	C10—C11—H11A	110.6
Ni1—O1—Ho1	105.95 (17)	N2—C11—H11B	110.6
C9—N1—C10	121.8 (5)	C10—C11—H11B	110.6
C9—N1—Ni1	126.3 (5)	H11A—C11—H11B	108.7
C10—N1—Ni1	111.9 (4)	N1—C10—C11	106.7 (5)
C12—N2—C11	119.2 (6)	N1—C10—H10A	110.4
C12—N2—Ni1	126.7 (5)	C11—C10—H10A	110.4
C11—N2—Ni1	113.9 (4)	N1—C10—H10B	110.4
O7—N3—O6	122.0 (7)	C11—C10—H10B	110.4
O7—N3—O5	122.8 (7)	H10A—C10—H10B	108.6
O6—N3—O5	115.3 (6)	N5—O11—Ho1	95.0 (4)
N3—O6—Ho1	95.8 (4)	C19—C20—H20A	109.5
N2—C12—C13	124.7 (6)	C19—C20—H20B	109.5
N2—C12—H12	117.7	H20A—C20—H20B	109.5
C13—C12—H12	117.7	C19—C20—H20C	109.5
C3—O3—C2	117.3 (5)	H20A—C20—H20C	109.5
C3—O3—Ho1	118.6 (3)	H20B—C20—H20C	109.5
C2—O3—Ho1	124.0 (4)	C3—C8—C7	119.0 (6)
O1—C18—C13	123.9 (6)	C3—C8—H8	120.5
O1—C18—C17	117.0 (5)	C7—C8—H8	120.5
C13—C18—C17	119.1 (6)	C6—C7—C8	121.7 (6)
C17—O4—C19	117.0 (5)	C6—C7—H7	119.1
C17—O4—Ho1	119.5 (4)	C8—C7—H7	119.1

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O12	0.96	2.41	3.088 (9)	127
C12—H12···O10i	0.93	2.37	3.286 (8)	169
C10—H10A···O10ii	0.97	2.42	3.301 (9)	150
C2—H2B···O11	0.97	2.59	3.015 (9)	107
C1—H1C···O11	0.96	2.52	3.173 (10)	125

Table 1

Selected bond lengths (Å)

Ho1—O1	2.390 (4)
Ho1—O2	2.343 (4)
Ho1—O3	2.540 (4)
Ho1—O4	2.594 (4)
Ho1—O5	2.430 (5)
Ho1—O6	2.468 (5)
Ho1—O8	2.460 (5)
Ho1—O9	2.492 (5)
Ho1—O11	2.531 (5)
Ho1—O12	2.425 (5)
Ni1—O1	1.846 (4)
Ni1—O2	1.847 (4)
Ni1—N1	1.837 (5)
Ni1—N2	1.837 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O10i	0.93	2.37	3.286 (8)	169
C10—H10A⋯O10ii	0.97	2.42	3.301 (9)	150

Symmetry codes: (i) ; (ii) .