{μ-6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}-μ-nitrato-dinitratoholmium(III)zinc(II)

Xiao, Y.-A.; Sui, Y.; Yi, X.-G.; Wu, J.-H.; Zhang, L.-P.

doi:10.1107/S1600536808013743

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m804-m805

doi:10.1107/S1600536808013743

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RETRACTED ARTICLE

This article has been retracted.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

Retracted: {μ-6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}-μ-nitrato-dinitratoholmium(III)zinc(II)

Yi-An Xiao,^a Yan Sui,^b ^* Xiu-Guang Yi,^b Jian-Hong Wu ^b and Li-Ping Zhang ^b

^aCollege of Life Science, JingGangShan University, 343009 Ji'an, JiangXi, People's Republic of China, and ^bJiangXi 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 Zn^II–Ho^III complex (systematic name: {μ-6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′)-μ-nitrato-1:2κ²O:O′-dinitrato-1κ⁴O,O′-holmium(III)zinc(II)), [HoZn(C₁₈H₁₈N₂O₄)(NO₃)₃], with the hexadentate Schiff base compartmental ligand N,N′-bis(3-methoxysalicylidene)ethylenediamine (H₂L), the Ho and Zn atoms are triply bridged by two phenolate O atoms of the Schiff base ligand and one nitrate ion. The five-coordinate Zn atom is in a square-pyramidal geometry with the donor centers of two imine N atoms, two phenolate O atoms and one of the bridging nitrate O atoms. The Ho^III center has a ninefold coordination environment of O atoms, involving the phenolate O atoms, two methoxy O atoms, two O atoms from two nitrate ions and one from the bridging nitrate ion. Weak intermolecular C—H⋯O interactions generate a two-dimensional double-layer structure.

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 , 2007 ).

Experimental

Crystal data

[HoZn(C₁₈H₁₈N₂O₄)(NO₃)₃]
M_r = 742.67
Monoclinic, P 2₁ /n
a = 10.694 (4) Å
b = 16.481 (7) Å
c = 14.921 (6) Å
β = 99.667 (6)°
V = 2592.4 (18) Å³
Z = 4
Mo Kα radiation
μ = 4.03 mm⁻¹
T = 293 (2) K
0.16 × 0.16 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.565, T_max = 0.689
15217 measured reflections
4499 independent reflections
3377 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.02
4499 reflections
345 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −1.18 e Å⁻³

Table 1
Selected bond lengths (Å)

Ho1—O1	2.293 (3)
Ho1—O2	2.298 (3)
Ho1—O3	2.604 (4)
Ho1—O4	2.604 (4)
Ho1—O6	2.323 (4)
Ho1—O8	2.448 (4)
Ho1—O9	2.481 (4)
Ho1—O11	2.430 (4)
Ho1—O12	2.468 (4)
Zn1—O1	2.005 (4)
Zn1—O2	2.022 (3)
Zn1—O5	1.979 (4)
Zn1—N1	2.047 (4)
Zn1—N2	2.021 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O11ⁱ	0.93	2.45	3.377 (7)	174
C10—H10A⋯O13ⁱⁱ	0.97	2.54	3.483 (8)	165
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+2.

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/S1600536808013743/at2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013743/at2567Isup2.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 3d-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 3d-4f hetorometallic Schiff base complexes (Sui et al. 2006; Sui et al. 2007), we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new Zn^II—Ho^III complex with salen-type Schiff base N,N'-bis(3-methoxysalicylidene) ethylenediamine (H₂L).

Complex (I) crystallizes in the space group P2₁/n, with zinc and holmium triply bridged by two phenolate O atoms provided by the Schiff base ligand and one nitrate ion. The inner salen-type cavity is occupied by zinc(II), while holmium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand.

The Ho^III center has a ninefold coordination environment of O atoms, involving the phenolate O atoms, two methoxy O atoms, two O atoms from two nitrate ions and one from the bridging nitrate ion. The four kinds of Ho—O bond distances are significantly different, the longest being the Ho—O (methoxy) separations and the shortest being the Ho—O (phenolate).

The Zn^II is in a square-pyramidal geometry and is five-coordinated by two imine N atoms, two phenolate O atoms and one of the bridging nitrate O atoms. The Zn atom is 0.6067 (4) Å below the mean N₂O₂ plane with an average deviation from the plane of 0.0380 (3) Å, which construct the bottom of square-pyramid. The Zn—O5 (bridging nitrate) separation is 1.979 (4) Å and the angles of this Zn—O vector with the Zn—N or Zn—O bonds lie between 102.5 (4)° and 112.6 (4)°, which suggesting that the Zn^II is in a slightly distorted square-pyramidal conformation.

Adjacent molecules are held together by weak interactions [C5(H5)···O11ⁱ= 3.377 (7) Å and C10(H10A)···O13ⁱⁱ= 3.483 (8) Å; symmetry codes: (i) -1/2 + x, 1/2 - y, 1/2 + z; (ii) 1 - x, -y, 2 - z]. These link the molecules into a two-dimensional double layer structure (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, 2007).

Experimental top

H₂L was prepared by the 2:1 condensation of 3-methoxysalicylaldehyde and ethylenediamine in methanol. Complex (I) was obtained by the treatment of zinc(II) acetate dihydrate (0.188 g, 1 mmol) with H₂L (0.328 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 C₁₈H₁₈HoN₅O₁₃Zn: C 29.11 H 2.44, Ho 22.21, N 9.43, Zn 8.80%; found: C 29.20, H 2.45, Ho 22.30, N 9.50, Zn 8.90%. IR (KBr, cm^-1): 1640 (C=N), 1386,1490 (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. All the H atoms on carbon have been omitted for clarity.
	Fig. 2. The packing diagram of (I), viewed along the b axis; hydrogen bonds are shown as dashed lines.

{µ-6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O¹,O^1',O⁶,O^6':2κ⁴O¹,N,N', O^1')-µ-nitrato-1:2κ²O:O'-dinitrato-1κ⁴O,O'- holmium(III)zinc(II)) top

Crystal data top

[HoZn(C₁₈H₁₈N₂O₄)(NO₃)₃]	F(000) = 1448
M_r = 742.67	D_x = 1.903 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5632 reflections
a = 10.694 (4) Å	θ = 2.2–25.3°
b = 16.481 (7) Å	µ = 4.03 mm⁻¹
c = 14.921 (6) Å	T = 293 K
β = 99.667 (6)°	Block, yellow
V = 2592.4 (18) Å³	0.16 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4499 independent reflections
Radiation source: fine-focus sealed tube	3377 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.565, T_max = 0.689	k = −19→19
15217 measured reflections	l = −17→17

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0558P)² + 0.1192P] where P = (F_o² + 2F_c²)/3
4499 reflections	(Δ/σ)_max < 0.001
345 parameters	Δρ_max = 0.61 e Å⁻³
2 restraints	Δρ_min = −1.18 e Å⁻³

Crystal data top

[HoZn(C₁₈H₁₈N₂O₄)(NO₃)₃]	V = 2592.4 (18) Å³
M_r = 742.67	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.694 (4) Å	µ = 4.03 mm⁻¹
b = 16.481 (7) Å	T = 293 K
c = 14.921 (6) Å	0.16 × 0.16 × 0.10 mm
β = 99.667 (6)°

Data collection top

Bruker APEXII area-detector diffractometer	4499 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3377 reflections with I > 2σ(I)
T_min = 0.565, T_max = 0.689	R_int = 0.037
15217 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.02	Δρ_max = 0.61 e Å⁻³
4499 reflections	Δρ_min = −1.18 e Å⁻³
345 parameters

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
Ho1	0.36187 (2)	0.109293 (15)	0.723858 (16)	0.04439 (11)
Zn1	0.21999 (6)	0.03550 (4)	0.88927 (4)	0.04303 (17)
O1	0.2906 (4)	0.1419 (2)	0.8559 (2)	0.0493 (9)
O12	0.5712 (4)	0.1290 (3)	0.8198 (3)	0.0640 (12)
O2	0.3521 (4)	−0.0016 (2)	0.8158 (2)	0.0497 (9)
O4	0.4894 (3)	−0.0201 (2)	0.6956 (2)	0.0495 (9)
C17	0.4119 (5)	−0.0722 (3)	0.8204 (3)	0.0413 (12)
O8	0.2843 (4)	0.1975 (2)	0.5945 (2)	0.0582 (10)
N4	0.2806 (5)	0.1437 (3)	0.5329 (4)	0.0624 (14)
O6	0.1491 (4)	0.0740 (3)	0.6881 (3)	0.0613 (11)
C3	0.2935 (6)	0.3590 (4)	0.8767 (4)	0.0567 (15)
H3	0.3175	0.4036	0.8452	0.068*
N5	0.6224 (5)	0.1590 (4)	0.7564 (4)	0.0659 (15)
O5	0.0581 (3)	0.0283 (2)	0.8031 (3)	0.0543 (10)
C16	0.4896 (5)	−0.0846 (3)	0.7542 (4)	0.0460 (13)
O9	0.3274 (4)	0.0751 (3)	0.5596 (3)	0.0624 (11)
C2	0.3092 (5)	0.2813 (3)	0.8465 (3)	0.0448 (13)
C12	0.4039 (5)	−0.1325 (3)	0.8854 (4)	0.0457 (13)
N3	0.0556 (5)	0.0490 (3)	0.7206 (4)	0.0695 (14)
O11	0.5537 (4)	0.1634 (3)	0.6792 (3)	0.0612 (11)
O10	0.2350 (6)	0.1567 (3)	0.4552 (3)	0.107 (2)
N1	0.1978 (4)	0.0839 (3)	1.0120 (3)	0.0506 (12)
N2	0.2494 (4)	−0.0675 (3)	0.9634 (3)	0.0488 (11)
C11	0.3278 (5)	−0.1246 (4)	0.9578 (4)	0.0513 (15)
H11	0.3374	−0.1641	1.0030	0.062*
C7	0.2716 (5)	0.2135 (3)	0.8916 (3)	0.0428 (12)
C8	0.1985 (5)	0.1588 (4)	1.0310 (4)	0.0573 (16)
H8	0.1823	0.1728	1.0884	0.069*
C10	0.1754 (6)	−0.0615 (4)	1.0385 (4)	0.0590 (16)
H10A	0.2017	−0.1037	1.0830	0.071*
H10B	0.0859	−0.0688	1.0151	0.071*
C6	0.2222 (5)	0.2248 (3)	0.9720 (4)	0.0500 (14)
C18	0.5665 (6)	−0.0292 (4)	0.6251 (4)	0.0638 (17)
H18A	0.6543	−0.0328	0.6524	0.096*
H18B	0.5544	0.0168	0.5852	0.096*
H18C	0.5421	−0.0777	0.5910	0.096*
C5	0.2056 (6)	0.3045 (4)	1.0014 (4)	0.0631 (17)
H5	0.1699	0.3130	1.0533	0.076*
O13	0.7311 (5)	0.1830 (4)	0.7710 (4)	0.112 (2)
C4	0.2412 (7)	0.3697 (4)	0.9550 (4)	0.0643 (18)
H4	0.2302	0.4219	0.9762	0.077*
C15	0.5530 (6)	−0.1572 (4)	0.7500 (4)	0.0569 (15)
H15	0.6023	−0.1659	0.7052	0.068*
C9	0.1972 (6)	0.0203 (4)	1.0823 (4)	0.0612 (17)
H9A	0.1307	0.0317	1.1174	0.073*
H9B	0.2777	0.0205	1.1234	0.073*
C14	0.5419 (6)	−0.2169 (4)	0.8140 (5)	0.0701 (19)
H14	0.5833	−0.2662	0.8113	0.084*
C13	0.4716 (6)	−0.2043 (4)	0.8802 (4)	0.0623 (17)
H13	0.4683	−0.2446	0.9235	0.075*
O7	−0.0708 (6)	0.0407 (5)	0.6557 (5)	0.142 (3)
O3	0.3629 (4)	0.2616 (2)	0.7706 (2)	0.0502 (9)
C1	0.4246 (7)	0.3260 (4)	0.7307 (4)	0.0661 (17)
H1A	0.3638	0.3673	0.7090	0.099*
H1B	0.4611	0.3051	0.6808	0.099*
H1C	0.4903	0.3486	0.7755	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ho1	0.05102 (19)	0.04515 (17)	0.04112 (16)	0.00162 (12)	0.01960 (11)	0.00255 (11)
Zn1	0.0470 (4)	0.0447 (4)	0.0411 (3)	−0.0003 (3)	0.0182 (3)	0.0028 (3)
O1	0.067 (3)	0.036 (2)	0.052 (2)	−0.0004 (19)	0.034 (2)	−0.0054 (18)
O12	0.050 (2)	0.091 (3)	0.053 (2)	−0.010 (2)	0.0144 (19)	0.013 (2)
O2	0.064 (3)	0.042 (2)	0.051 (2)	0.0077 (19)	0.0327 (19)	0.0102 (17)
O4	0.060 (2)	0.048 (2)	0.047 (2)	0.0107 (19)	0.0264 (18)	0.0023 (18)
C17	0.035 (3)	0.037 (3)	0.051 (3)	0.003 (2)	0.006 (2)	0.000 (3)
O8	0.081 (3)	0.049 (2)	0.045 (2)	0.013 (2)	0.014 (2)	0.0020 (19)
N4	0.076 (4)	0.063 (3)	0.053 (3)	0.018 (3)	0.024 (3)	0.004 (3)
O6	0.058 (3)	0.074 (3)	0.052 (2)	−0.010 (2)	0.0101 (18)	0.007 (2)
C3	0.068 (4)	0.039 (3)	0.060 (4)	0.001 (3)	0.003 (3)	0.001 (3)
N5	0.056 (4)	0.079 (4)	0.068 (4)	−0.008 (3)	0.024 (3)	0.003 (3)
O5	0.047 (2)	0.055 (2)	0.064 (2)	−0.0028 (19)	0.0182 (19)	0.0082 (19)
C16	0.044 (3)	0.047 (3)	0.048 (3)	0.004 (3)	0.010 (2)	−0.002 (3)
O9	0.088 (3)	0.055 (3)	0.047 (2)	0.015 (2)	0.021 (2)	0.000 (2)
C2	0.053 (3)	0.035 (3)	0.045 (3)	0.003 (3)	0.004 (2)	−0.001 (2)
C12	0.041 (3)	0.044 (3)	0.053 (3)	−0.002 (3)	0.009 (3)	0.002 (3)
N3	0.065 (3)	0.072 (4)	0.072 (3)	−0.007 (3)	0.015 (3)	0.010 (3)
O11	0.060 (3)	0.079 (3)	0.048 (2)	−0.007 (2)	0.021 (2)	0.014 (2)
O10	0.154 (5)	0.118 (5)	0.043 (3)	0.058 (4)	0.003 (3)	0.004 (3)
N1	0.052 (3)	0.062 (3)	0.044 (3)	−0.005 (2)	0.024 (2)	−0.001 (2)
N2	0.047 (3)	0.052 (3)	0.049 (3)	0.001 (2)	0.015 (2)	0.010 (2)
C11	0.049 (4)	0.053 (4)	0.050 (3)	−0.007 (3)	0.003 (3)	0.011 (3)
C7	0.043 (3)	0.049 (3)	0.037 (3)	−0.001 (3)	0.008 (2)	−0.012 (3)
C8	0.055 (4)	0.078 (5)	0.044 (3)	0.000 (3)	0.025 (3)	−0.013 (3)
C10	0.056 (4)	0.070 (4)	0.055 (3)	−0.006 (3)	0.021 (3)	0.024 (3)
C6	0.058 (4)	0.048 (3)	0.045 (3)	0.001 (3)	0.012 (3)	−0.013 (3)
C18	0.071 (4)	0.068 (4)	0.063 (4)	0.011 (3)	0.040 (3)	0.003 (3)
C5	0.069 (4)	0.072 (5)	0.051 (3)	0.010 (4)	0.016 (3)	−0.022 (3)
O13	0.064 (3)	0.173 (6)	0.100 (4)	−0.036 (4)	0.021 (3)	0.026 (4)
C4	0.085 (5)	0.051 (4)	0.056 (4)	0.013 (4)	0.009 (3)	−0.016 (3)
C15	0.053 (4)	0.055 (4)	0.065 (4)	0.014 (3)	0.018 (3)	−0.007 (3)
C9	0.065 (4)	0.077 (5)	0.046 (3)	0.000 (3)	0.023 (3)	0.007 (3)
C14	0.067 (4)	0.046 (4)	0.102 (5)	0.021 (3)	0.025 (4)	0.006 (4)
C13	0.062 (4)	0.045 (4)	0.080 (4)	0.009 (3)	0.013 (3)	0.020 (3)
O7	0.099 (5)	0.175 (7)	0.138 (6)	−0.011 (5)	−0.026 (4)	−0.001 (5)
O3	0.067 (3)	0.038 (2)	0.049 (2)	−0.0051 (19)	0.0216 (18)	0.0003 (18)
C1	0.092 (5)	0.048 (4)	0.063 (4)	−0.013 (4)	0.026 (3)	0.005 (3)

Geometric parameters (Å, º) top

Ho1—O1	2.293 (3)	C2—C7	1.398 (7)
Ho1—O2	2.298 (3)	C12—C13	1.396 (8)
Ho1—O3	2.604 (4)	C12—C11	1.463 (8)
Ho1—O4	2.604 (4)	N3—O7	1.531 (8)
Ho1—O6	2.323 (4)	N1—C8	1.267 (8)
Ho1—O8	2.448 (4)	N1—C9	1.484 (7)
Ho1—O9	2.481 (4)	N2—C11	1.273 (7)
Ho1—O11	2.430 (4)	N2—C10	1.480 (6)
Ho1—O12	2.468 (4)	C11—H11	0.9300
Zn1—O1	2.005 (4)	C7—C6	1.401 (7)
Zn1—O2	2.022 (3)	C8—C6	1.449 (8)
Zn1—O5	1.979 (4)	C8—H8	0.9300
Zn1—N1	2.047 (4)	C10—C9	1.498 (9)
Zn1—N2	2.021 (5)	C10—H10A	0.9700
O1—C7	1.324 (6)	C10—H10B	0.9700
O12—N5	1.269 (6)	C6—C5	1.406 (8)
O2—C17	1.325 (6)	C18—H18A	0.9600
O4—C16	1.376 (6)	C18—H18B	0.9600
O4—C18	1.449 (6)	C18—H18C	0.9600
C17—C12	1.402 (7)	C5—C4	1.367 (9)
C17—C16	1.408 (7)	C5—H5	0.9300
O8—N4	1.273 (6)	C4—H4	0.9300
N4—O10	1.199 (6)	C15—C14	1.390 (9)
N4—O9	1.272 (6)	C15—H15	0.9300
O6—N3	1.251 (6)	C9—H9A	0.9700
C3—C2	1.379 (8)	C9—H9B	0.9700
C3—C4	1.389 (9)	C14—C13	1.355 (9)
C3—H3	0.9300	C14—H14	0.9300
N5—O13	1.213 (7)	C13—H13	0.9300
N5—O11	1.260 (6)	O3—C1	1.431 (6)
O5—N3	1.274 (6)	C1—H1A	0.9600
C16—C15	1.382 (8)	C1—H1B	0.9600
C2—O3	1.390 (6)	C1—H1C	0.9600

O1—Ho1—O2	67.54 (12)	C15—C16—C17	120.6 (5)
O1—Ho1—O6	78.56 (14)	N4—O9—Ho1	95.4 (3)
O2—Ho1—O6	78.26 (14)	C3—C2—O3	124.9 (5)
O1—Ho1—O11	124.55 (14)	C3—C2—C7	121.6 (5)
O2—Ho1—O11	125.51 (14)	O3—C2—C7	113.4 (4)
O6—Ho1—O11	150.31 (13)	C13—C12—C17	118.0 (5)
O1—Ho1—O8	114.92 (13)	C13—C12—C11	118.3 (5)
O2—Ho1—O8	154.15 (14)	C17—C12—C11	123.7 (5)
O6—Ho1—O8	77.22 (14)	O6—N3—O5	125.0 (5)
O11—Ho1—O8	75.84 (14)	O6—N3—O7	117.5 (5)
O1—Ho1—O12	82.58 (14)	O5—N3—O7	117.4 (5)
O2—Ho1—O12	83.46 (14)	N5—O11—Ho1	96.7 (3)
O6—Ho1—O12	157.61 (13)	C8—N1—C9	122.1 (5)
O11—Ho1—O12	52.07 (13)	C8—N1—Zn1	125.6 (4)
O8—Ho1—O12	122.24 (14)	C9—N1—Zn1	111.8 (4)
O1—Ho1—O9	152.44 (15)	C11—N2—C10	122.7 (5)
O2—Ho1—O9	113.29 (14)	C11—N2—Zn1	129.0 (4)
O6—Ho1—O9	74.88 (14)	C10—N2—Zn1	107.7 (4)
O11—Ho1—O9	78.74 (14)	N2—C11—C12	124.6 (5)
O8—Ho1—O9	51.77 (13)	N2—C11—H11	117.7
O12—Ho1—O9	124.92 (14)	C12—C11—H11	117.7
O1—Ho1—O4	126.16 (12)	O1—C7—C2	116.2 (4)
O2—Ho1—O4	61.54 (11)	O1—C7—C6	124.6 (5)
O6—Ho1—O4	106.10 (14)	C2—C7—C6	119.1 (5)
O11—Ho1—O4	76.52 (13)	N1—C8—C6	126.2 (5)
O8—Ho1—O4	118.41 (12)	N1—C8—H8	116.9
O12—Ho1—O4	75.69 (14)	C6—C8—H8	116.9
O9—Ho1—O4	69.45 (12)	N2—C10—C9	109.0 (5)
O1—Ho1—O3	62.03 (12)	N2—C10—H10A	109.9
O2—Ho1—O3	127.20 (12)	C9—C10—H10A	109.9
O6—Ho1—O3	105.25 (14)	N2—C10—H10B	109.9
O11—Ho1—O3	75.75 (13)	C9—C10—H10B	109.9
O8—Ho1—O3	67.95 (12)	H10A—C10—H10B	108.3
O12—Ho1—O3	75.82 (14)	C7—C6—C5	118.5 (6)
O9—Ho1—O3	118.46 (12)	C7—C6—C8	123.4 (5)
O4—Ho1—O3	148.63 (12)	C5—C6—C8	117.8 (5)
O5—Zn1—O1	102.49 (16)	O4—C18—H18A	109.5
O5—Zn1—N2	110.09 (18)	O4—C18—H18B	109.5
O1—Zn1—N2	147.12 (18)	H18A—C18—H18B	109.5
O5—Zn1—O2	104.16 (16)	O4—C18—H18C	109.5
O1—Zn1—O2	78.64 (14)	H18A—C18—H18C	109.5
N2—Zn1—O2	89.09 (16)	H18B—C18—H18C	109.5
O5—Zn1—N1	112.60 (18)	C4—C5—C6	121.1 (6)
O1—Zn1—N1	89.23 (17)	C4—C5—H5	119.5
N2—Zn1—N1	82.44 (19)	C6—C5—H5	119.5
O2—Zn1—N1	143.00 (18)	C5—C4—C3	120.8 (6)
C7—O1—Zn1	126.1 (3)	C5—C4—H4	119.6
C7—O1—Ho1	130.6 (3)	C3—C4—H4	119.6
Zn1—O1—Ho1	101.65 (15)	C16—C15—C14	118.9 (6)
N5—O12—Ho1	94.7 (3)	C16—C15—H15	120.5
C17—O2—Zn1	127.8 (3)	C14—C15—H15	120.5
C17—O2—Ho1	131.3 (3)	N1—C9—C10	110.3 (5)
Zn1—O2—Ho1	100.93 (15)	N1—C9—H9A	109.6
C16—O4—C18	116.2 (4)	C10—C9—H9A	109.6
C16—O4—Ho1	118.3 (3)	N1—C9—H9B	109.6
C18—O4—Ho1	125.5 (3)	C10—C9—H9B	109.6
O2—C17—C12	125.0 (5)	H9A—C9—H9B	108.1
O2—C17—C16	115.3 (5)	C13—C14—C15	121.0 (6)
C12—C17—C16	119.7 (5)	C13—C14—H14	119.5
N4—O8—Ho1	96.9 (3)	C15—C14—H14	119.5
O10—N4—O9	122.4 (5)	C14—C13—C12	121.8 (6)
O10—N4—O8	122.1 (5)	C14—C13—H13	119.1
O9—N4—O8	115.4 (5)	C12—C13—H13	119.1
N3—O6—Ho1	144.0 (4)	C2—O3—C1	116.6 (4)
C2—C3—C4	118.8 (6)	C2—O3—Ho1	117.3 (3)
C2—C3—H3	120.6	C1—O3—Ho1	125.8 (3)
C4—C3—H3	120.6	O3—C1—H1A	109.5
O13—N5—O11	122.6 (5)	O3—C1—H1B	109.5
O13—N5—O12	120.9 (6)	H1A—C1—H1B	109.5
O11—N5—O12	116.5 (5)	O3—C1—H1C	109.5
N3—O5—Zn1	119.1 (3)	H1A—C1—H1C	109.5
O4—C16—C15	126.0 (5)	H1B—C1—H1C	109.5
O4—C16—C17	113.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O11	0.96	2.54	3.167 (8)	123
C5—H5···O11ⁱ	0.93	2.45	3.377 (7)	174
C10—H10A···O13ⁱⁱ	0.97	2.54	3.483 (8)	165
C18—H18B···O9	0.96	2.58	3.100 (8)	114

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

Experimental details

Crystal data
Chemical formula	[HoZn(C₁₈H₁₈N₂O₄)(NO₃)₃]
M_r	742.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.694 (4), 16.481 (7), 14.921 (6)
β (°)	99.667 (6)
V (Å³)	2592.4 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.03
Crystal size (mm)	0.16 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.565, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	15217, 4499, 3377
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.02
No. of reflections	4499
No. of parameters	345
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −1.18

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

Selected bond lengths (Å) top

Ho1—O1	2.293 (3)	Ho1—O11	2.430 (4)
Ho1—O2	2.298 (3)	Ho1—O12	2.468 (4)
Ho1—O3	2.604 (4)	Zn1—O1	2.005 (4)
Ho1—O4	2.604 (4)	Zn1—O2	2.022 (3)
Ho1—O6	2.323 (4)	Zn1—O5	1.979 (4)
Ho1—O8	2.448 (4)	Zn1—N1	2.047 (4)
Ho1—O9	2.481 (4)	Zn1—N2	2.021 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O11ⁱ	0.93	2.45	3.377 (7)	173.9
C10—H10A···O13ⁱⁱ	0.97	2.54	3.483 (8)	164.7

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

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
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
Sui, Y., He, D.-Y., Fang, X.-N., Chen, L. & Peng, J.-L. (2007). Acta Cryst. E63, m2013–m2014. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages m804-m805

doi:10.1107/S1600536808013743

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

Retracted: {μ-6,6′-Dimeth­­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}-μ-nitrato-dinitratoholmium(III)zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: {μ-6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}-μ-nitrato-dinitratoholmium(III)zinc(II)