{6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ4O1,O1′,O6,O6′:2κ4O1,N,N′,O1′}(ethanol-1κO)-μ-nitrato-1:2κ2O:O′-dinitrato-1κ4O,O′-samarium(III)zinc(II)

Huang, Q.; Sui, Y.-H.; Zhang, G.-X.

doi:10.1107/S1600536809033558

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1161-m1162

doi:10.1107/S1600536809033558

Open

access

RETRACTED ARTICLE

This article has been retracted.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

Retracted: {6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}(ethanol-1κO)-μ-nitrato-1:2κ²O:O′-dinitrato-1κ⁴O,O′-samarium(III)zinc(II)

Qiang Huang,^a ^* Yu-Hua Sui ^b and Guo-Xiang Zhang ^c

^aCollege of Mechanical and Materials Engineering, Jiujiang University, 332005 Jiujiang, JiangXi, People's Republic of China, ^bVacational Education Center of JiLin Oil Feild, 131200 SongYuan, JiLin, People's Republic of China, and ^cThe Pipeline Tools Subsidiary, Well Drilling Technology and Service Corporation of Jilin Oil Field, 131200 SongYuan, JiLin, People's Republic of China
^*Correspondence e-mail: qhuang111@163.com

(Received 13 August 2009; accepted 23 August 2009; online 5 September 2009)

In the title heteronuclear Zn^II–Sm^III complex, [SmZn(C₁₈H₁₈N₂O₄)(NO₃)₃(CH₃CH₂OH)], with the hexadentate Schiff base compartmental ligand N,N′-bis(3-methoxysalicylidene)ethylenediamine (H₂L), the Sm^III and Zn^II ions are triply bridged by two phenolate O atoms from the Schiff base ligand and one nitrate anion. The five-coordinate Zn^II ion is in a square-pyramidal geometry formed by the donor centers of two imine N atoms, two phenolate O atoms and one of the bridging nitrate O atoms. The Sm^III center is in a ten-fold coordination of O atoms, involving the phenolate O atoms, two methoxy O atoms, one ethanol O atom, and two O atoms from two nitrate anions and one from the bridging nitrate anion. In the crystal, intermolecular O—H⋯O and C—H⋯O interactions generate a layer structure extending parallel to (101).

Related literature

For the preparation, magnetic and optical properties of 3d-4f hetorometallic dinuclear complexes, see: Baggio et al. (2000 ); Caravan et al. (1999 ); Edder et al. (2000 ); Knoer et al. (2005 ).

Experimental

Crystal data

[SmZn(C₁₈H₁₈N₂O₄)(NO₃)₃(C₂H₆O)]
M_r = 774.16
Monoclinic, P 2₁ /n
a = 9.975 (3) Å
b = 13.780 (4) Å
c = 19.889 (6) Å
β = 91.745 (4)°
V = 2732.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 293 K
0.26 × 0.23 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.501, T_max = 0.592
16112 measured reflections
4741 independent reflections
4175 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.079
S = 1.08
4741 reflections
377 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O9	0.96	2.52	3.237 (6)	132
O14—H14S⋯O6ⁱ	0.855 (19)	1.87 (2)	2.718 (4)	171 (5)
C8—H8⋯O11ⁱⁱ	0.93	2.55	3.440 (5)	160
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033558/at2862sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033558/at2862Isup2.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). we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new Zn^II—Sm^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 samarium triply bridged by two phenolate O atoms provided by a salen-type Schiff base ligand and one nitrate. The inner salen-type cavity is occupied by zinc(II), while samarium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand.

The Sm^III center has a decacoordination environment of O atoms, involving the phenolate O atoms, two methoxy O atoms, one ethanol O atom, two O atoms from two nitrates and one from the bridging nitrate. The five kinds of Sm—O bond distances are significantly different, the longest being the Sm—O(methoxy) separations and the shortest being the Sm—O5(bridging nitrate).

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.

Adjacent molecules are held together by typical O—H···O hydrogen bonds and weak C—H···O interactions. these link the molecules into a two-dimensional layer structure(Fig 2).

Related literature top

For the preparation, magnetic and optical

properties of 3d-4f hetorometallic dinuclear complexes, see: Baggio et al. (2000); Caravan et al. (1999); Edder et al. (2000); Knoer et al. (2005).

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 ethanol solution (80 ml) under reflux for 3 h and then for another 3 h after the addition of samarium(III) nitrate hexahydrate(0.444 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 ethanol solution. Analysis calculated for C₂₀H₂₄N₅O₁₄SmZn: C 31.03, H 3.12, N 9.05, Sm 19.42, Zn 8.45%; found: C 31.10, H 2.98, N 8.99, Sm 20.01, Zn 8.40%. IR(KBr, cm^-1): 1640(C=N), 1386,1490(nitrate).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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, 2009).

Figures top

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

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

Crystal data top

[SmZn(C₁₈H₁₈N₂O₄)(NO₃)₃(C₂H₆O)]	F(000) = 1532
M_r = 774.16	D_x = 1.882 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5725 reflections
a = 9.975 (3) Å	θ = 2.5–28.2°
b = 13.780 (4) Å	µ = 3.08 mm⁻¹
c = 19.889 (6) Å	T = 293 K
β = 91.745 (4)°	Block, yellow
V = 2732.4 (13) Å³	0.26 × 0.23 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4741 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.501, T_max = 0.592	k = −15→16
16112 measured reflections	l = −23→23

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.045P)² + 4.1668P] where P = (F_o² + 2F_c²)/3
4741 reflections	(Δ/σ)_max < 0.001
377 parameters	Δρ_max = 0.67 e Å⁻³
3 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

[SmZn(C₁₈H₁₈N₂O₄)(NO₃)₃(C₂H₆O)]	V = 2732.4 (13) Å³
M_r = 774.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.975 (3) Å	µ = 3.08 mm⁻¹
b = 13.780 (4) Å	T = 293 K
c = 19.889 (6) Å	0.26 × 0.23 × 0.19 mm
β = 91.745 (4)°

Data collection top

Bruker APEXII area-detector diffractometer	4741 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4175 reflections with I > 2σ(I)
T_min = 0.501, T_max = 0.592	R_int = 0.021
16112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	3 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.67 e Å⁻³
4741 reflections	Δρ_min = −0.70 e Å⁻³
377 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
C1	0.5387 (4)	0.1513 (4)	0.1046 (2)	0.0435 (11)
H1A	0.6226	0.1846	0.1108	0.065*
H1B	0.5050	0.1609	0.0594	0.065*
H1C	0.5517	0.0832	0.1126	0.065*
C2	0.4878 (4)	0.1904 (3)	0.21745 (19)	0.0287 (8)
C3	0.4091 (4)	0.2491 (3)	0.25846 (18)	0.0248 (8)
C4	0.4475 (4)	0.2570 (3)	0.32728 (19)	0.0309 (9)
C5	0.5626 (4)	0.2059 (3)	0.3513 (2)	0.0405 (11)
H5	0.5894	0.2119	0.3963	0.049*
C6	0.6343 (5)	0.1489 (4)	0.3106 (2)	0.0468 (12)
H6	0.7083	0.1151	0.3280	0.056*
C7	0.5978 (4)	0.1404 (3)	0.2430 (2)	0.0416 (10)
H7	0.6473	0.1011	0.2150	0.050*
C8	0.3727 (4)	0.3097 (3)	0.37649 (19)	0.0325 (9)
H8	0.4042	0.3070	0.4209	0.039*
C9	0.1883 (5)	0.4013 (3)	0.4187 (2)	0.0419 (11)
H9A	0.1913	0.4716	0.4174	0.050*
H9B	0.2236	0.3797	0.4621	0.050*
C10	0.0444 (5)	0.3652 (4)	0.4069 (2)	0.0432 (11)
H10A	0.0380	0.2976	0.4201	0.052*
H10B	−0.0162	0.4027	0.4340	0.052*
C11	−0.1155 (4)	0.3718 (3)	0.3160 (2)	0.0376 (10)
H11	−0.1793	0.3652	0.3488	0.045*
C12	−0.1630 (4)	0.3768 (3)	0.2471 (2)	0.0337 (9)
C13	−0.3008 (4)	0.3975 (3)	0.2340 (3)	0.0454 (11)
H13	−0.3576	0.4041	0.2700	0.054*
C14	−0.3520 (4)	0.4080 (3)	0.1702 (3)	0.0482 (12)
H14	−0.4427	0.4212	0.1631	0.058*
C15	−0.2698 (4)	0.3991 (3)	0.1159 (2)	0.0419 (11)
H15	−0.3044	0.4081	0.0724	0.050*
C16	−0.1355 (4)	0.3769 (3)	0.1268 (2)	0.0327 (9)
C17	−0.0801 (4)	0.3635 (3)	0.1915 (2)	0.0291 (8)
C18	−0.0918 (5)	0.3868 (4)	0.0095 (2)	0.0523 (13)
H18A	−0.1594	0.3406	−0.0040	0.078*
H18B	−0.0188	0.3835	−0.0207	0.078*
H18C	−0.1295	0.4509	0.0085	0.078*
C19	0.0334 (4)	0.0595 (3)	0.1448 (3)	0.0453 (11)
H19A	0.0360	0.0054	0.1761	0.054*
H19B	0.0421	0.0337	0.0998	0.054*
C20	−0.0964 (5)	0.1103 (4)	0.1492 (3)	0.0640 (15)
H20A	−0.1040	0.1376	0.1934	0.096*
H20B	−0.1683	0.0651	0.1409	0.096*
H20C	−0.1014	0.1612	0.1163	0.096*
H14S	0.189 (4)	0.093 (3)	0.1907 (18)	0.045 (14)*
N1	0.2671 (4)	0.3598 (3)	0.36409 (16)	0.0334 (8)
N2	0.0069 (4)	0.3757 (3)	0.33567 (17)	0.0365 (8)
N3	0.2742 (4)	0.5201 (3)	0.18223 (18)	0.0429 (8)
N4	0.3575 (4)	0.3693 (3)	−0.00107 (19)	0.0461 (10)
N5	0.1636 (4)	0.1430 (3)	−0.00124 (17)	0.0380 (8)
O1	0.3020 (3)	0.29131 (19)	0.22943 (13)	0.0285 (6)
O2	0.0480 (2)	0.3360 (2)	0.19722 (13)	0.0310 (6)
O3	0.4443 (3)	0.1886 (2)	0.15072 (13)	0.0340 (6)
O4	−0.0437 (3)	0.3650 (2)	0.07643 (14)	0.0378 (7)
O5	0.2537 (3)	0.4574 (2)	0.13814 (15)	0.0460 (8)
O6	0.2370 (3)	0.5111 (2)	0.24316 (13)	0.0334 (6)
O7	0.3498 (5)	0.6110 (3)	0.1638 (3)	0.0920 (15)
O8	0.4194 (3)	0.3382 (2)	0.05096 (16)	0.0441 (7)
O9	0.2306 (3)	0.3687 (2)	−0.00015 (14)	0.0422 (7)
O10	0.4160 (5)	0.3958 (4)	−0.0499 (2)	0.0997 (17)
O11	0.0688 (3)	0.1928 (2)	0.02181 (14)	0.0383 (7)
O12	0.2775 (3)	0.1549 (2)	0.02628 (15)	0.0408 (7)
O13	0.1458 (4)	0.0871 (3)	−0.04800 (19)	0.0694 (11)
O14	0.1442 (3)	0.1242 (2)	0.16021 (15)	0.0361 (7)
Sm1	0.209482 (19)	0.287372 (15)	0.113944 (9)	0.02816 (9)
Zn1	0.17006 (4)	0.38157 (3)	0.27338 (2)	0.02711 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.035 (2)	0.060 (3)	0.036 (2)	0.016 (2)	0.0029 (18)	−0.011 (2)
C2	0.0245 (19)	0.034 (2)	0.027 (2)	−0.0018 (16)	−0.0040 (15)	0.0050 (16)
C3	0.0228 (19)	0.028 (2)	0.0233 (19)	−0.0031 (15)	−0.0020 (14)	0.0067 (15)
C4	0.028 (2)	0.038 (2)	0.027 (2)	−0.0031 (17)	−0.0074 (16)	0.0051 (17)
C5	0.035 (2)	0.058 (3)	0.028 (2)	0.001 (2)	−0.0093 (18)	0.0101 (19)
C6	0.036 (2)	0.058 (3)	0.046 (3)	0.012 (2)	−0.012 (2)	0.015 (2)
C7	0.036 (2)	0.045 (3)	0.044 (3)	0.0095 (19)	0.0013 (19)	0.007 (2)
C8	0.036 (2)	0.041 (2)	0.0203 (19)	−0.0063 (18)	−0.0052 (16)	0.0038 (17)
C9	0.056 (3)	0.049 (3)	0.021 (2)	0.003 (2)	0.0044 (18)	−0.0073 (19)
C10	0.052 (3)	0.053 (3)	0.026 (2)	0.004 (2)	0.0140 (19)	−0.0007 (19)
C11	0.035 (2)	0.036 (2)	0.043 (3)	−0.0011 (18)	0.0172 (19)	−0.0053 (19)
C12	0.026 (2)	0.031 (2)	0.045 (2)	−0.0022 (16)	0.0072 (17)	−0.0053 (18)
C13	0.028 (2)	0.041 (3)	0.068 (3)	−0.0012 (19)	0.015 (2)	−0.008 (2)
C14	0.022 (2)	0.049 (3)	0.074 (4)	0.0056 (19)	−0.004 (2)	−0.007 (2)
C15	0.029 (2)	0.038 (3)	0.057 (3)	0.0059 (18)	−0.010 (2)	−0.005 (2)
C16	0.029 (2)	0.027 (2)	0.042 (2)	0.0032 (16)	−0.0028 (17)	−0.0083 (17)
C17	0.025 (2)	0.024 (2)	0.038 (2)	0.0009 (15)	0.0006 (16)	−0.0061 (16)
C18	0.051 (3)	0.066 (3)	0.039 (3)	0.017 (2)	−0.013 (2)	−0.001 (2)
C19	0.038 (3)	0.038 (3)	0.060 (3)	−0.002 (2)	−0.002 (2)	0.006 (2)
C20	0.036 (3)	0.059 (3)	0.097 (5)	−0.002 (2)	0.009 (3)	−0.003 (3)
N1	0.043 (2)	0.0359 (19)	0.0215 (16)	−0.0051 (16)	0.0014 (14)	−0.0033 (14)
N2	0.040 (2)	0.041 (2)	0.0291 (18)	−0.0007 (16)	0.0111 (15)	0.0003 (15)
N3	0.058 (2)	0.038 (2)	0.0329 (14)	0.0040 (17)	0.0048 (15)	−0.0028 (12)
N4	0.053 (3)	0.048 (2)	0.038 (2)	0.0035 (18)	0.0141 (18)	0.0109 (18)
N5	0.047 (2)	0.038 (2)	0.0287 (18)	−0.0019 (17)	−0.0023 (16)	−0.0059 (16)
O1	0.0244 (14)	0.0385 (16)	0.0221 (14)	0.0051 (11)	−0.0042 (10)	−0.0010 (11)
O2	0.0226 (13)	0.0421 (16)	0.0282 (14)	0.0061 (12)	−0.0005 (11)	−0.0067 (12)
O3	0.0251 (14)	0.0489 (17)	0.0279 (15)	0.0091 (12)	−0.0016 (11)	−0.0054 (12)
O4	0.0317 (15)	0.0516 (18)	0.0298 (15)	0.0093 (13)	−0.0054 (12)	−0.0056 (13)
O5	0.071 (2)	0.0360 (17)	0.0308 (15)	−0.0057 (15)	0.0056 (15)	−0.0015 (11)
O6	0.0410 (16)	0.0288 (15)	0.0303 (12)	−0.0026 (12)	0.0015 (11)	−0.0031 (11)
O7	0.114 (4)	0.069 (3)	0.095 (4)	−0.018 (3)	0.033 (3)	−0.002 (2)
O8	0.0332 (16)	0.053 (2)	0.0460 (19)	−0.0035 (14)	−0.0014 (13)	0.0090 (15)
O9	0.0420 (18)	0.054 (2)	0.0309 (16)	0.0052 (14)	−0.0023 (13)	0.0070 (14)
O10	0.085 (3)	0.143 (5)	0.074 (3)	0.015 (3)	0.042 (3)	0.058 (3)
O11	0.0355 (16)	0.0480 (18)	0.0310 (16)	0.0025 (13)	−0.0073 (12)	−0.0040 (13)
O12	0.0341 (17)	0.0488 (19)	0.0393 (17)	0.0041 (13)	−0.0037 (13)	−0.0085 (14)
O13	0.082 (3)	0.069 (3)	0.056 (2)	−0.001 (2)	−0.013 (2)	−0.036 (2)
O14	0.0323 (16)	0.0368 (17)	0.0386 (17)	−0.0058 (12)	−0.0078 (13)	0.0112 (13)
Sm1	0.02985 (13)	0.03342 (14)	0.02110 (13)	0.00080 (8)	−0.00085 (8)	−0.00187 (8)
Zn1	0.0286 (2)	0.0328 (3)	0.0200 (2)	−0.00050 (18)	0.00205 (17)	−0.00135 (17)

Geometric parameters (Å, º) top

C1—O3	1.430 (5)	C17—O2	1.334 (5)
C1—H1A	0.9600	C18—O4	1.433 (5)
C1—H1B	0.9600	C18—H18A	0.9600
C1—H1C	0.9600	C18—H18B	0.9600
C2—C7	1.379 (6)	C18—H18C	0.9600
C2—O3	1.384 (5)	C19—O14	1.446 (5)
C2—C3	1.406 (6)	C19—C20	1.477 (7)
C3—O1	1.333 (4)	C19—H19A	0.9700
C3—C4	1.414 (5)	C19—H19B	0.9700
C4—C5	1.418 (6)	C20—H20A	0.9600
C4—C8	1.444 (6)	C20—H20B	0.9600
C5—C6	1.348 (7)	C20—H20C	0.9600
C5—H5	0.9300	N1—Zn1	2.043 (3)
C6—C7	1.387 (6)	N2—Zn1	2.077 (3)
C6—H6	0.9300	N3—O5	1.244 (5)
C7—H7	0.9300	N3—O6	1.284 (4)
C8—N1	1.277 (5)	N3—O7	1.512 (6)
C8—H8	0.9300	N4—O10	1.205 (5)
C9—N1	1.474 (5)	N4—O8	1.264 (5)
C9—C10	1.530 (7)	N4—O9	1.267 (5)
C9—H9A	0.9700	N5—O13	1.217 (5)
C9—H9B	0.9700	N5—O12	1.257 (4)
C10—N2	1.462 (5)	N5—O11	1.265 (5)
C10—H10A	0.9700	O1—Zn1	2.028 (3)
C10—H10B	0.9700	O1—Sm1	2.450 (3)
C11—N2	1.272 (6)	O2—Zn1	2.014 (3)
C11—C12	1.438 (6)	O2—Sm1	2.439 (3)
C11—H11	0.9300	O3—Sm1	2.787 (3)
C12—C17	1.413 (6)	O4—Sm1	2.822 (3)
C12—C13	1.420 (6)	O5—Sm1	2.429 (3)
C13—C14	1.362 (7)	O6—Zn1	2.004 (3)
C13—H13	0.9300	O8—Sm1	2.570 (3)
C14—C15	1.380 (7)	O9—Sm1	2.545 (3)
C14—H14	0.9300	O11—Sm1	2.621 (3)
C15—C16	1.385 (6)	O12—Sm1	2.627 (3)
C15—H15	0.9300	O14—Sm1	2.523 (3)
C16—O4	1.387 (5)	O14—H14S	0.855 (19)
C16—C17	1.398 (6)

O3—C1—H1A	109.5	O5—N3—O7	118.5 (4)
O3—C1—H1B	109.5	O6—N3—O7	118.0 (3)
H1A—C1—H1B	109.5	O10—N4—O8	121.8 (4)
O3—C1—H1C	109.5	O10—N4—O9	121.5 (4)
H1A—C1—H1C	109.5	O8—N4—O9	116.7 (3)
H1B—C1—H1C	109.5	O13—N5—O12	121.7 (4)
C7—C2—O3	124.6 (4)	O13—N5—O11	121.8 (4)
C7—C2—C3	121.7 (4)	O12—N5—O11	116.6 (3)
O3—C2—C3	113.7 (3)	C3—O1—Zn1	127.1 (2)
O1—C3—C2	117.0 (3)	C3—O1—Sm1	132.1 (2)
O1—C3—C4	125.1 (3)	Zn1—O1—Sm1	100.77 (10)
C2—C3—C4	117.8 (3)	C17—O2—Zn1	122.1 (2)
C3—C4—C5	118.7 (4)	C17—O2—Sm1	132.1 (2)
C3—C4—C8	124.4 (4)	Zn1—O2—Sm1	101.52 (10)
C5—C4—C8	116.8 (4)	C2—O3—C1	115.4 (3)
C6—C5—C4	121.8 (4)	C2—O3—Sm1	118.7 (2)
C6—C5—H5	119.1	C1—O3—Sm1	124.9 (2)
C4—C5—H5	119.1	C16—O4—C18	115.8 (3)
C5—C6—C7	120.1 (4)	C16—O4—Sm1	117.3 (2)
C5—C6—H6	119.9	C18—O4—Sm1	126.7 (3)
C7—C6—H6	119.9	N3—O5—Sm1	146.6 (3)
C2—C7—C6	119.9 (4)	N3—O6—Zn1	118.6 (2)
C2—C7—H7	120.1	N4—O8—Sm1	96.1 (2)
C6—C7—H7	120.1	N4—O9—Sm1	97.2 (2)
N1—C8—C4	125.5 (4)	N5—O11—Sm1	97.6 (2)
N1—C8—H8	117.3	N5—O12—Sm1	97.6 (2)
C4—C8—H8	117.3	C19—O14—Sm1	132.6 (2)
N1—C9—C10	106.2 (3)	C19—O14—H14S	103 (3)
N1—C9—H9A	110.5	Sm1—O14—H14S	125 (3)
C10—C9—H9A	110.5	O5—Sm1—O2	73.74 (10)
N1—C9—H9B	110.5	O5—Sm1—O1	74.45 (10)
C10—C9—H9B	110.5	O2—Sm1—O1	66.10 (9)
H9A—C9—H9B	108.7	O5—Sm1—O14	146.58 (10)
N2—C10—C9	109.1 (3)	O2—Sm1—O14	79.28 (10)
N2—C10—H10A	109.9	O1—Sm1—O14	76.81 (9)
C9—C10—H10A	109.9	O5—Sm1—O9	74.48 (10)
N2—C10—H10B	109.9	O2—Sm1—O9	123.96 (10)
C9—C10—H10B	109.9	O1—Sm1—O9	141.92 (10)
H10A—C10—H10B	108.3	O14—Sm1—O9	138.33 (10)
N2—C11—C12	125.3 (4)	O5—Sm1—O8	71.83 (11)
N2—C11—H11	117.4	O2—Sm1—O8	145.17 (10)
C12—C11—H11	117.4	O1—Sm1—O8	99.31 (9)
C17—C12—C13	118.0 (4)	O14—Sm1—O8	130.09 (10)
C17—C12—C11	123.7 (4)	O9—Sm1—O8	49.82 (10)
C13—C12—C11	118.2 (4)	O5—Sm1—O11	135.09 (10)
C14—C13—C12	121.6 (4)	O2—Sm1—O11	105.13 (9)
C14—C13—H13	119.2	O1—Sm1—O11	147.66 (9)
C12—C13—H13	119.2	O14—Sm1—O11	70.91 (9)
C13—C14—C15	120.4 (4)	O9—Sm1—O11	69.69 (10)
C13—C14—H14	119.8	O8—Sm1—O11	102.80 (10)
C15—C14—H14	119.8	O5—Sm1—O12	138.80 (10)
C14—C15—C16	119.5 (4)	O2—Sm1—O12	146.17 (9)
C14—C15—H15	120.3	O1—Sm1—O12	122.69 (9)
C16—C15—H15	120.3	O14—Sm1—O12	72.40 (10)
C15—C16—O4	124.8 (4)	O9—Sm1—O12	71.60 (10)
C15—C16—C17	121.8 (4)	O8—Sm1—O12	68.60 (10)
O4—C16—C17	113.5 (3)	O11—Sm1—O12	48.25 (9)
O2—C17—C16	117.8 (3)	O5—Sm1—O3	105.83 (10)
O2—C17—C12	123.5 (4)	O2—Sm1—O3	121.53 (8)
C16—C17—C12	118.6 (4)	O1—Sm1—O3	58.34 (8)
O4—C18—H18A	109.5	O14—Sm1—O3	72.15 (9)
O4—C18—H18B	109.5	O9—Sm1—O3	110.93 (9)
H18A—C18—H18B	109.5	O8—Sm1—O3	64.54 (9)
O4—C18—H18C	109.5	O11—Sm1—O3	111.62 (9)
H18A—C18—H18C	109.5	O12—Sm1—O3	66.62 (8)
H18B—C18—H18C	109.5	O5—Sm1—O4	80.93 (10)
O14—C19—C20	111.1 (4)	O2—Sm1—O4	58.08 (8)
O14—C19—H19A	109.4	O1—Sm1—O4	123.23 (8)
C20—C19—H19A	109.4	O14—Sm1—O4	101.26 (9)
O14—C19—H19B	109.4	O9—Sm1—O4	72.24 (9)
C20—C19—H19B	109.4	O8—Sm1—O4	120.25 (9)
H19A—C19—H19B	108.0	O11—Sm1—O4	63.13 (9)
C19—C20—H20A	109.5	O12—Sm1—O4	109.57 (9)
C19—C20—H20B	109.5	O3—Sm1—O4	173.01 (9)
H20A—C20—H20B	109.5	O6—Zn1—O2	104.55 (12)
C19—C20—H20C	109.5	O6—Zn1—O1	100.96 (11)
H20A—C20—H20C	109.5	O2—Zn1—O1	82.54 (10)
H20B—C20—H20C	109.5	O6—Zn1—N1	104.02 (13)
C8—N1—C9	121.5 (3)	O2—Zn1—N1	151.32 (13)
C8—N1—Zn1	128.0 (3)	O1—Zn1—N1	89.69 (12)
C9—N1—Zn1	110.2 (3)	O6—Zn1—N2	119.22 (13)
C11—N2—C10	120.6 (4)	O2—Zn1—N2	88.27 (13)
C11—N2—Zn1	125.5 (3)	O1—Zn1—N2	139.80 (13)
C10—N2—Zn1	113.6 (3)	N1—Zn1—N2	79.99 (14)
O5—N3—O6	123.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O12	0.96	2.35	2.995 (5)	125
C18—H18B···O9	0.96	2.52	3.237 (6)	132
O14—H14S···O6ⁱ	0.86 (2)	1.87 (2)	2.718 (4)	171 (5)
C8—H8···O11ⁱⁱ	0.93	2.55	3.440 (5)	160

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

Experimental details

Crystal data
Chemical formula	[SmZn(C₁₈H₁₈N₂O₄)(NO₃)₃(C₂H₆O)]
M_r	774.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.975 (3), 13.780 (4), 19.889 (6)
β (°)	91.745 (4)
V (Å³)	2732.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.26 × 0.23 × 0.19

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.501, 0.592
No. of measured, independent and observed [I > 2σ(I)] reflections	16112, 4741, 4175
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.079, 1.08
No. of reflections	4741
No. of parameters	377
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.70

Computer programs: , SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), APEX2 (Bruker, 2004) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O9	0.96	2.52	3.237 (6)	131.8
O14—H14S···O6ⁱ	0.855 (19)	1.87 (2)	2.718 (4)	171 (5)
C8—H8···O11ⁱⁱ	0.93	2.55	3.440 (5)	159.6

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

Acknowledgements

We gratefully acknowledge financial support from the Educational Commission of Jiangxi Province of China (GJJ08448) and the Natural Science Foundation of Jiangxi Province of China (2008GQC0002).

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, SAINT 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
Westrip, S. P. (2009). 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 65| Part 10| October 2009| Pages m1161-m1162

doi:10.1107/S1600536809033558

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: {6,6′-Dimeth­­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato-1κ4O1,O1′,O6,O6′:2κ4O1,N,N′,O1′}(ethanol-1κO)-μ-nitrato-1:2κ2O:O′-dinitrato-1κ4O,O′-samarium(III)zinc(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Retracted: {6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}(ethanol-1κO)-μ-nitrato-1:2κ²O:O′-dinitrato-1κ⁴O,O′-samarium(III)zinc(II)