metal-organic compounds
Bis[μ-N-(2-oxidobenzylidene)pyridine-2-carbohydrazidato]bis[chlorido(methanol-κO)erbium(III)]
aCollege of Chemistry and Chemical Engineering, Yan'an University, Yan'an, Shaanxi 716000, People's Republic of China
*Correspondence e-mail: yanghua7687@163.com
In the binuclear title complex, [Er2(C13H9N3O2)2Cl2(CH3OH)2], the entire molecule is generated by the application of inversion symmetry. Each ErIII ion is seven-coordinated by two O atoms and one N atom from one N-(2-oxidobenzylidene)pyridine-2-carbohydrazidate (L2−) ligand, one O atom and one N atom from the symmetry-related L2− ligand, one O atom of a methanol molecule and one chloride anion. The coordination geometry is based on a pseudo-pentagonal bipyramid. Linear supramolecular chains along [010] are formed in the crystal packing through O—H⋯Cl hydrogen bonds.
Related literature
For complexes containing salicylaldehyde-2-pyridinecarboxyl-hydrazone and related ligands, see: Guo et al. (2011a,b); Bai et al. (2005, 2006); Wu et al. (2004); Milway et al. (2003). For the mechanism of the hydrolysis of salicylaldehyde thiosemicarbazone, see: Narang & Aggarwal (1974).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812013979/tk5069sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812013979/tk5069Isup2.hkl
A mixture of ErCl3.6H2O (0.0762 g, 0.2 mmol), α-pyridoin (0.0214 g, 0.1 mmol), salicylaldehyde thiosemicarbazone (0.0390 g, 0.2 mmol) and CH3OH (2 ml) was sealed in a 6 ml Pyrex-tube. The tube was heated at 393 K for 3 days under autogenous pressure. Cooling of the resultant solution to room temperature gave yellow crystals. The crystals were collected by filtration, washed with CH3OH (2 ml) and dried in air.
The H atoms were placed in calculated positions with O—H = 0.95 Å and C—H = 0.95–0.98 Å, and with Uiso(H) = 1.2–1.5Ueq(C, O).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Er2(C13H9N3O2)2Cl2(CH4O)2] | F(000) = 908 |
Mr = 947.97 | Dx = 2.089 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4466 reflections |
a = 9.5810 (4) Å | θ = 2.7–28.1° |
b = 7.0906 (3) Å | µ = 5.76 mm−1 |
c = 22.3504 (8) Å | T = 128 K |
β = 96.920 (3)° | Block, yellow |
V = 1507.31 (10) Å3 | 0.15 × 0.13 × 0.12 mm |
Z = 2 |
Bruker SMART CCD diffractometer | 3732 independent reflections |
Radiation source: fine-focus sealed tube | 2931 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ scans and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker 2000) | h = −12→11 |
Tmin = 0.479, Tmax = 0.545 | k = −9→9 |
14182 measured reflections | l = −29→29 |
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) = 0.059 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0299P)2] where P = (Fo2 + 2Fc2)/3 |
3732 reflections | (Δ/σ)max = 0.004 |
200 parameters | Δρmax = 1.25 e Å−3 |
0 restraints | Δρmin = −0.71 e Å−3 |
[Er2(C13H9N3O2)2Cl2(CH4O)2] | V = 1507.31 (10) Å3 |
Mr = 947.97 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.5810 (4) Å | µ = 5.76 mm−1 |
b = 7.0906 (3) Å | T = 128 K |
c = 22.3504 (8) Å | 0.15 × 0.13 × 0.12 mm |
β = 96.920 (3)° |
Bruker SMART CCD diffractometer | 3732 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2000) | 2931 reflections with I > 2σ(I) |
Tmin = 0.479, Tmax = 0.545 | Rint = 0.040 |
14182 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.25 e Å−3 |
3732 reflections | Δρmin = −0.71 e Å−3 |
200 parameters |
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 | ||
Er1 | 0.372121 (17) | 0.91591 (3) | 0.432040 (7) | 0.02740 (6) | |
O2 | 0.5836 (3) | 1.0615 (4) | 0.46548 (11) | 0.0323 (6) | |
O3 | 0.2988 (3) | 1.2290 (5) | 0.42893 (15) | 0.0526 (8) | |
H7 | 0.3591 | 1.3150 | 0.4521 | 0.063* | |
C5 | 0.6425 (4) | 1.0757 (5) | 0.36561 (16) | 0.0289 (8) | |
Cl1 | 0.48595 (13) | 0.58790 (16) | 0.42195 (5) | 0.0476 (3) | |
N1 | 0.5108 (3) | 1.0104 (5) | 0.34970 (14) | 0.0282 (7) | |
O1 | 0.1993 (3) | 0.8698 (4) | 0.36235 (12) | 0.0386 (7) | |
C14 | 0.0511 (4) | 0.7742 (6) | 0.46482 (18) | 0.0366 (9) | |
H14 | −0.0122 | 0.7498 | 0.4935 | 0.044* | |
C8 | 0.0727 (4) | 0.7952 (5) | 0.35398 (17) | 0.0306 (9) | |
C6 | 0.6814 (4) | 1.1036 (5) | 0.43082 (17) | 0.0287 (8) | |
N3 | 0.1753 (3) | 0.8294 (5) | 0.48577 (14) | 0.0308 (7) | |
N4 | 0.8066 (3) | 1.1581 (5) | 0.45048 (14) | 0.0344 (8) | |
C1 | 0.4695 (4) | 0.9753 (6) | 0.29156 (18) | 0.0343 (9) | |
H1 | 0.3765 | 0.9309 | 0.2802 | 0.041* | |
C4 | 0.7340 (4) | 1.1077 (6) | 0.32293 (18) | 0.0373 (10) | |
H4 | 0.8257 | 1.1559 | 0.3347 | 0.045* | |
C10 | −0.1348 (5) | 0.6619 (7) | 0.3905 (2) | 0.0435 (11) | |
H10 | −0.1858 | 0.6313 | 0.4230 | 0.052* | |
C12 | −0.1223 (5) | 0.6715 (7) | 0.2860 (2) | 0.0440 (11) | |
H12 | −0.1625 | 0.6447 | 0.2459 | 0.053* | |
C9 | −0.0018 (4) | 0.7457 (6) | 0.40305 (17) | 0.0332 (8) | |
C3 | 0.6899 (5) | 1.0688 (6) | 0.26356 (19) | 0.0413 (10) | |
H3 | 0.7513 | 1.0886 | 0.2338 | 0.050* | |
C13 | 0.0074 (4) | 0.7590 (6) | 0.29574 (18) | 0.0366 (9) | |
H13 | 0.0532 | 0.7954 | 0.2621 | 0.044* | |
C2 | 0.5561 (5) | 1.0008 (7) | 0.24736 (18) | 0.0393 (10) | |
H2 | 0.5241 | 0.9721 | 0.2065 | 0.047* | |
C11 | −0.1934 (5) | 0.6230 (7) | 0.3332 (2) | 0.0499 (12) | |
H11 | −0.2825 | 0.5629 | 0.3262 | 0.060* | |
C7 | 0.1756 (6) | 1.3080 (8) | 0.3970 (3) | 0.0722 (17) | |
H7A | 0.1078 | 1.2075 | 0.3850 | 0.108* | |
H7B | 0.2000 | 1.3728 | 0.3609 | 0.108* | |
H7C | 0.1341 | 1.3985 | 0.4229 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Er1 | 0.02276 (9) | 0.03156 (11) | 0.02796 (10) | −0.00645 (8) | 0.00334 (6) | −0.00213 (8) |
O2 | 0.0269 (13) | 0.0435 (18) | 0.0273 (14) | −0.0087 (12) | 0.0062 (10) | −0.0013 (12) |
O3 | 0.0461 (19) | 0.0366 (19) | 0.073 (2) | 0.0010 (15) | −0.0021 (15) | −0.0050 (17) |
C5 | 0.0294 (18) | 0.027 (2) | 0.0304 (19) | −0.0045 (16) | 0.0041 (15) | 0.0008 (17) |
Cl1 | 0.0544 (7) | 0.0371 (6) | 0.0535 (7) | 0.0029 (5) | 0.0145 (5) | 0.0048 (5) |
N1 | 0.0286 (16) | 0.0276 (17) | 0.0285 (17) | −0.0043 (13) | 0.0038 (13) | −0.0008 (14) |
O1 | 0.0266 (14) | 0.054 (2) | 0.0347 (16) | −0.0102 (13) | 0.0012 (11) | −0.0015 (13) |
C14 | 0.0283 (19) | 0.042 (3) | 0.040 (2) | −0.0070 (18) | 0.0065 (16) | −0.003 (2) |
C8 | 0.0251 (18) | 0.032 (2) | 0.034 (2) | 0.0003 (15) | −0.0017 (15) | −0.0056 (17) |
C6 | 0.0285 (19) | 0.031 (2) | 0.0273 (19) | −0.0042 (16) | 0.0040 (14) | −0.0006 (16) |
N3 | 0.0264 (16) | 0.0361 (19) | 0.0299 (17) | −0.0075 (14) | 0.0033 (13) | −0.0026 (14) |
N4 | 0.0288 (17) | 0.046 (2) | 0.0289 (18) | −0.0093 (15) | 0.0066 (14) | −0.0029 (15) |
C1 | 0.035 (2) | 0.038 (3) | 0.029 (2) | −0.0038 (17) | 0.0004 (16) | 0.0010 (18) |
C4 | 0.032 (2) | 0.045 (3) | 0.035 (2) | −0.0083 (19) | 0.0059 (16) | 0.003 (2) |
C10 | 0.035 (2) | 0.048 (3) | 0.046 (3) | −0.012 (2) | 0.0013 (19) | −0.002 (2) |
C12 | 0.036 (2) | 0.047 (3) | 0.046 (3) | −0.003 (2) | −0.0083 (19) | −0.011 (2) |
C9 | 0.0263 (18) | 0.036 (2) | 0.036 (2) | −0.0036 (18) | 0.0003 (15) | −0.0054 (19) |
C3 | 0.041 (2) | 0.049 (3) | 0.036 (2) | 0.002 (2) | 0.0135 (18) | 0.005 (2) |
C13 | 0.033 (2) | 0.040 (2) | 0.036 (2) | 0.0003 (19) | 0.0012 (16) | −0.006 (2) |
C2 | 0.044 (2) | 0.047 (3) | 0.026 (2) | 0.000 (2) | −0.0002 (18) | 0.0001 (19) |
C11 | 0.037 (2) | 0.050 (3) | 0.060 (3) | −0.018 (2) | −0.007 (2) | −0.005 (2) |
C7 | 0.069 (4) | 0.058 (4) | 0.088 (4) | 0.019 (3) | 0.003 (3) | 0.013 (3) |
Er1—O1 | 2.157 (3) | C6—N4 | 1.286 (5) |
Er1—O2i | 2.284 (3) | N3—N4i | 1.417 (4) |
Er1—O2 | 2.316 (3) | N4—N3i | 1.417 (4) |
Er1—O3 | 2.327 (3) | C1—C2 | 1.376 (6) |
Er1—N3 | 2.433 (3) | C1—H1 | 0.9500 |
Er1—N1 | 2.488 (3) | C4—C3 | 1.371 (6) |
Er1—Cl1 | 2.5901 (12) | C4—H4 | 0.9500 |
O2—C6 | 1.320 (4) | C10—C11 | 1.362 (6) |
O2—Er1i | 2.284 (3) | C10—C9 | 1.403 (5) |
O3—C7 | 1.419 (6) | C10—H10 | 0.9500 |
O3—H7 | 0.9500 | C12—C11 | 1.369 (7) |
C5—N1 | 1.351 (5) | C12—C13 | 1.382 (6) |
C5—C4 | 1.390 (5) | C12—H12 | 0.9500 |
C5—C6 | 1.474 (5) | C3—C2 | 1.377 (6) |
N1—C1 | 1.335 (5) | C3—H3 | 0.9500 |
O1—C8 | 1.316 (4) | C13—H13 | 0.9500 |
C14—N3 | 1.286 (5) | C2—H2 | 0.9500 |
C14—C9 | 1.427 (5) | C11—H11 | 0.9500 |
C14—H14 | 0.9500 | C7—H7A | 0.9800 |
C8—C13 | 1.398 (5) | C7—H7B | 0.9800 |
C8—C9 | 1.423 (5) | C7—H7C | 0.9800 |
O1—Er1—O2i | 140.21 (10) | O1—C8—C13 | 120.5 (4) |
O1—Er1—O2 | 149.99 (10) | O1—C8—C9 | 122.0 (3) |
O2i—Er1—O2 | 66.16 (10) | C13—C8—C9 | 117.5 (3) |
O1—Er1—O3 | 85.42 (12) | N4—C6—O2 | 124.5 (3) |
O2i—Er1—O3 | 88.97 (11) | N4—C6—C5 | 119.5 (3) |
O2—Er1—O3 | 80.42 (11) | O2—C6—C5 | 115.9 (3) |
O1—Er1—N3 | 75.24 (10) | C14—N3—N4i | 112.4 (3) |
O2i—Er1—N3 | 65.42 (10) | C14—N3—Er1 | 129.4 (3) |
O2—Er1—N3 | 130.77 (10) | N4i—N3—Er1 | 118.2 (2) |
O3—Er1—N3 | 90.34 (11) | C6—N4—N3i | 111.0 (3) |
O1—Er1—N1 | 86.47 (10) | N1—C1—C2 | 122.7 (4) |
O2i—Er1—N1 | 132.20 (10) | N1—C1—H1 | 118.6 |
O2—Er1—N1 | 66.06 (9) | C2—C1—H1 | 118.6 |
O3—Er1—N1 | 84.69 (11) | C3—C4—C5 | 119.0 (4) |
N3—Er1—N1 | 161.38 (11) | C3—C4—H4 | 120.5 |
O1—Er1—Cl1 | 95.50 (9) | C5—C4—H4 | 120.5 |
O2i—Er1—Cl1 | 96.94 (7) | C11—C10—C9 | 122.4 (4) |
O2—Er1—Cl1 | 93.86 (7) | C11—C10—H10 | 118.8 |
O3—Er1—Cl1 | 169.37 (9) | C9—C10—H10 | 118.8 |
N3—Er1—Cl1 | 100.15 (8) | C11—C12—C13 | 120.8 (4) |
N1—Er1—Cl1 | 84.80 (8) | C11—C12—H12 | 119.6 |
O1—Er1—Er1i | 167.32 (8) | C13—C12—H12 | 119.6 |
O2i—Er1—Er1i | 33.34 (6) | C10—C9—C8 | 118.5 (4) |
O2—Er1—Er1i | 32.82 (6) | C10—C9—C14 | 117.5 (4) |
O3—Er1—Er1i | 83.65 (8) | C8—C9—C14 | 123.9 (3) |
N3—Er1—Er1i | 98.39 (7) | C4—C3—C2 | 119.6 (4) |
N1—Er1—Er1i | 98.87 (7) | C4—C3—H3 | 120.2 |
Cl1—Er1—Er1i | 96.43 (3) | C2—C3—H3 | 120.2 |
C6—O2—Er1i | 120.9 (2) | C12—C13—C8 | 121.5 (4) |
C6—O2—Er1 | 124.5 (2) | C12—C13—H13 | 119.3 |
Er1i—O2—Er1 | 113.84 (10) | C8—C13—H13 | 119.3 |
C7—O3—Er1 | 128.4 (3) | C1—C2—C3 | 118.7 (4) |
C7—O3—H7 | 115.8 | C1—C2—H2 | 120.7 |
Er1—O3—H7 | 115.8 | C3—C2—H2 | 120.7 |
N1—C5—C4 | 121.5 (4) | C10—C11—C12 | 119.2 (4) |
N1—C5—C6 | 115.0 (3) | C10—C11—H11 | 120.4 |
C4—C5—C6 | 123.5 (3) | C12—C11—H11 | 120.4 |
C1—N1—C5 | 118.5 (3) | O3—C7—H7A | 109.5 |
C1—N1—Er1 | 123.2 (3) | O3—C7—H7B | 109.5 |
C5—N1—Er1 | 117.6 (2) | H7A—C7—H7B | 109.5 |
C8—O1—Er1 | 141.0 (2) | O3—C7—H7C | 109.5 |
N3—C14—C9 | 126.9 (4) | H7A—C7—H7C | 109.5 |
N3—C14—H14 | 116.5 | H7B—C7—H7C | 109.5 |
C9—C14—H14 | 116.5 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H7···Cl1ii | 0.95 | 2.42 | 3.128 (4) | 131 |
Symmetry code: (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Er2(C13H9N3O2)2Cl2(CH4O)2] |
Mr | 947.97 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 128 |
a, b, c (Å) | 9.5810 (4), 7.0906 (3), 22.3504 (8) |
β (°) | 96.920 (3) |
V (Å3) | 1507.31 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 5.76 |
Crystal size (mm) | 0.15 × 0.13 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker 2000) |
Tmin, Tmax | 0.479, 0.545 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14182, 3732, 2931 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.059, 0.99 |
No. of reflections | 3732 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.25, −0.71 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Er1—O1 | 2.157 (3) | Er1—N3 | 2.433 (3) |
Er1—O2i | 2.284 (3) | Er1—N1 | 2.488 (3) |
Er1—O2 | 2.316 (3) | Er1—Cl1 | 2.5901 (12) |
Er1—O3 | 2.327 (3) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H7···Cl1ii | 0.95 | 2.42 | 3.128 (4) | 131 |
Symmetry code: (ii) x, y+1, z. |
Acknowledgements
The author appreciates financial support from Yanan University (grant No. YD2011–20) and the Science and Technology Bureau of Yanan City (grant No. kn2009–16).
References
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The chemistry of coordination complexes supported by salicylaldehyde-2-pyridinecarboxyl-hydrazone (H2L) and its derivatives has received intensive attention as these form coordination complexes with aesthetically pleasing structures and intriguing magnetic behaviour (Guo et al., 2011a,b). A handful of transition metal complexes based on the H2L ligand have been prepared (Bai et al., 2005; Wu et al., 2004; Bai et al., 2006; Milway et al., 2003), but no complex containing rare earth elements has been reported to date. Herein, we report the structure of a new dinuclear ErIII complex (Scheme 1). The complex was synthesized by the 2:1:1 reaction of ErCl3.6H2O/α-pyridoin/salicylaldehyde thiosemicarbazone under solvothermal conditions. The X-ray analysis reveals that the centrosymmetric complex consists of two ErIII ions, two L2- ligands, two Cl- ions and two methanol molecules, Fig. 1 and Table 1. The intermolecular O—H···Cl hydrogen bonds, Table 2, lead to linear supramolecular chains along [010] (Fig. 2).
The remarkable structural feature of the complex is the presence of the in situ formed H2L ligand, which was proposed to be constructed by the reaction of picolinic acid, hydrazine and salicylaldehyde. The picolinic acid was assumed to be derived from the hydrolysis of α-pyridoin, and hydrazine and salicylaldehyde were believed to be originated from the hydrolysis of salicylaldehyde thiosemicarbazone (Narang & Aggarwal, 1974).