{μ-6,6′-Dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}trinitratoholmium(III)nickel(II)

Xiao, Y.-A.; Fu, X.-K.; Sui, Y.; Wu, Q.; Xiong, S.-H.

doi:10.1107/S1600536808013755

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m806-m807

doi:10.1107/S1600536808013755

Open

access

RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: {μ-6,6′-Diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}trinitratoholmium(III)nickel(II)

Yi-An Xiao,^a Xiang-Kai Fu,^b Yan Sui,^c ^* Qing Wu ^c and Shao-Hui Xiong ^c

^aCollege of Life Sciences, JingGangShan University, 343009 Ji'an, JiangXi, People's Republic of China, ^bCollege of Chemistry & Chemical Engineering, Southwest University, 400715 Beibei, Chongqing, People's Republic of China, and ^cJiangXi Province Key Laboratory of Coordination Chemistry, College of Chemistry & Chemical Engineering, JingGangShan University, 343009 Ji'an, JiangXi, People's Republic of China
^*Correspondence e-mail: ysui@163.com

(Received 6 May 2008; accepted 8 May 2008; online 14 May 2008)

In the title heteronuclear Ni^II–Ho^III complex (systematic name: {μ-6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}trinitrato-1κ⁶O,O′-holmium(III)nickel(II)), [HoNi(C₂₀H₂₂N₂O₄)(NO₃)₃], with the hexadentate Schiff base compartmental ligand N,N′-bis(3-ethoxysalicylidene)ethylenediamine (H₂L), 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 ethoxy O atoms and two O atoms each from the three nitrates. Weak C—H⋯O and O⋯Ni [3.383 (4) Å] interactions 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_r = 764.07
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.04
5970 reflections
364 parameters
H-atom parameters constrained
Δρ_max = 2.00 e Å⁻³
Δρ_min = −0.61 e Å⁻³
Absolute structure: Flack (1983 ), 2455 Friedel pairs
Flack parameter: −0.003 (18)

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The potential applications of trivalent lanthanide complexes as contrast agent for magnetic resonance imaging and stains for fluorescence imaging have prompted considerable interest in the preparation, magnetic and optical properties of 3 d-4f hetorometallic dinuclear complexes (Baggio et al., 2000; Caravan et al., 1999; Edder et al., 2000; Knoer et al., 2005). As part of our investigations into the structure and applications of 3 d-4f hetorometallic Schiff base complexes(Sui et al. 2006), we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new Ni^II—Ho^III complex with salen-type Schiff base N,N'-bis(3-ethoxysalicylidene) ethylenediamine(H₂L).

Complex (I) crystallizes in the space group P2₁2₁2₁, with nickel and holmium doubly bridged by two phenolate O atoms provided by a salen-type Schiff base ligand. The inner salen-type cavity is occupied by nickel(II), while holmium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand. The dihedral angles between the mean planes of Ni1/O1/O2 and Ho1/O1/O2 is 6.97 (26)° suggesting that the bridging moiety is almost planar; the deviation of atoms from the least squares Ni1/O1/O2/Ho1 plane being -0.0583 (2)Å for Ni, -0.0397 (3)Å for Ho, 0.0483 (2)Å for O1 and 0.0497 (2)Å for O2.

The holmium(III) center in (I) has a decacoordination environment of O atoms. In addition to the phenolate ligands, two ethoxy O atoms coordinate to this metal center, two O atoms from each of the three nitrates chelate to holmium to complete the decacoordination. The three kinds of Ho—O bond distances are significantly different, the shortest being the Ho—O(phenolate) and longest being the Ho—O(ethoxy) separations.

The coordination of nickel(II) is approximately square planar. The donor centers are alternatively above and below the mean N₂O₂ plane with an average deviation from the plane of 0.0698 (2) Å, while Ni1 is 0.0022 (2)Å above this square plane.

Adjacent molecules are held together by weak interactions (O13···Ni1=3.383 (4) Å, C10—H10A···O10ⁱ=3.301 (9), and C12—H12···O10ⁱⁱ=3.286 (8); symmetry codes:(i)x - 1, y, z; (ii)-x, 1/2 + y, 1/2 - z.) these link the molecules into a two-dimensional zigzag sheet(Fig 2).

Related literature top

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 top

H₂L was prepared by the 2:1 condensation of 3-ethoxysalicylaldehyde and ethylenediamine in methanol. Complex (I) was obtained by the treatment of nickel(II) acetate tetrahydrate (0.217 g, 1 mmol) with H₂L(0.356 g, 1 mmol) in methanol solution (80 ml) under reflux for 3 h and then for another 3 h after the addition of holmium(III) nitrate hexahydrate (0.459 g, 1 mmol). The reaction mixture was cooled and the resulting precipitate was filtered off, washed with diethyl ether and dried in vacuo. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation at room temperature of a methanol solution. Analysis calculated for C₂₀H₂₂HoN₅NiO₁₃: C 31.44, H 2.90, Ho 21.59, N 9.17, Ni 7.68%; found: C 31.85, H 2.95, Ho 21.55, N 9.24, Ni 7.78. IR(KBr, cm^-1): 1645(C=N), 1385,1491(nitrate).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram of (I), viewed along the b axis; hydrogen bonds are shown as dashed lines.

{µ-6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O¹,O^1',O⁶,O^6': 2κ⁴O¹,N,N',O^1''}trinitrato-1κ⁶O,O'-holmium(III) nickel(II)) top

Crystal data top

[HoNi(C₂₀H₂₂N₂O₄)(NO₃)₃]	F(000) = 1504
M_r = 764.07	D_x = 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 = 1.9–28.3°
b = 13.7028 (14) Å	µ = 3.98 mm⁻¹
c = 21.203 (2) Å	T = 293 K
V = 2493.6 (4) Å³	Block, red
Z = 4	0.17 × 0.16 × 0.13 mm

Data collection top

Bruker APEXII area-detector diffractometer	5970 independent reflections
Radiation source: fine-focus sealed tube	4299 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.559, T_max = 0.626	k = −17→18
18705 measured reflections	l = −27→27

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 2.00 e Å⁻³
5970 reflections	Δρ_min = −0.61 e Å⁻³
364 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	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	Absolute structure parameter: −0.003 (18)

Crystal data top

[HoNi(C₂₀H₂₂N₂O₄)(NO₃)₃]	V = 2493.6 (4) Å³
M_r = 764.07	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5825 (8) Å	µ = 3.98 mm⁻¹
b = 13.7028 (14) Å	T = 293 K
c = 21.203 (2) Å	0.17 × 0.16 × 0.13 mm

Data collection top

Bruker APEXII area-detector diffractometer	5970 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4299 reflections with I > 2σ(I)
T_min = 0.559, T_max = 0.626	R_int = 0.055
18705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.113	Δρ_max = 2.00 e Å⁻³
S = 1.04	Δρ_min = −0.61 e Å⁻³
5970 reflections	Absolute structure: Flack (1983), 2455 Friedel pairs
364 parameters	Absolute structure parameter: −0.003 (18)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[HoNi(C₂₀H₂₂N₂O₄)(NO₃)₃]
M_r	764.07
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.5825 (8), 13.7028 (14), 21.203 (2)
V (Å³)	2493.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.98
Crystal size (mm)	0.17 × 0.16 × 0.13

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.559, 0.626
No. of measured, independent and observed [I > 2σ(I)] reflections	18705, 5970, 4299
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.04
No. of reflections	5970
No. of parameters	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.00, −0.61
Absolute structure	Flack (1983), 2455 Friedel pairs
Absolute structure parameter	−0.003 (18)

Computer programs: , SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), APEX2 (Bruker, 2004) and publCIF (Westrip, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O10ⁱ	0.93	2.37	3.286 (8)	168.7
C10—H10A···O10ⁱⁱ	0.97	2.42	3.301 (9)	150.1

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z.

Acknowledgements

We gratefully acknowledge financial support from the Department of Education, JiangXi Province (No. 2007317) and the Natural Science Foundation of JiangXi Province (No. 2007GZH1667).

References

Baggio, R., Garland, M. T., Moreno, Y., Pena, O., Perec, M. & Spodine, E. (2000). J. Chem. Soc. Dalton Trans. pp. 2061–2066. Web of Science CSD CrossRef Google Scholar
Bruker (2004). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Caravan, P., Ellison, J. J., McMurry, T. J. & Lauffer, R. B. (1999). Chem. Rev. 99, 2293–2352. Web of Science CrossRef PubMed CAS Google Scholar
Edder, C., Piguet, C., Bernardinelli, G., Mareda, J., Bochet, C. G., Bunzli, J.-C. G. & Hopfgartner, G. (2000). Inorg. Chem. 39, 5059–5073. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Knoer, R., Lin, H.-H., Wei, H.-H. & Mohanta, S. (2005). Inorg. Chem. 44, 3524–3536. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sui, Y., Fang, X.-N., Xiao, Y.-A., Luo, Q.-Y. & Li, M.-H. (2006). Acta Cryst. E62, m2230–m2232. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m806-m807

doi:10.1107/S1600536808013755

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Retracted: {μ-6,6′-Dieth­­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}trinitratoholmium(III)nickel(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: {μ-6,6′-Diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}trinitratoholmium(III)nickel(II)