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Bis[6-methoxy-2-[(4-methylphenyl)iminiomethyl]phenolate-κO1]tris(nitrato-κ2O,O′)ytterbium(III) monohydrate
aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China, and College of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
*Correspondence e-mail: sky53@zjnu.cn
The 3)3(C15H15NO2)2]·H2O, contains two Schiff base 2-[(4-methylphenyl)iminomethyl]-6-methoxyphenol (HL) ligands, three independent nitrate ions that chelate to the ytterbium(III) ion in an O,O′-bidentate manner and an uncoordinated water molecule. The of the YbIII ion is eight. The HL ligands chelate with a strong Yb—O(phenolate) bond and a weak Yb—O(methoxy) contact. The latter augments the to give a YbO10 bicapped square antiprism. Classical intermolecular O—H⋯O and N—H⋯O hydrogen bonds as well as weak C—H⋯O contacts contribute to the stability of the structure.
of title compound, [Yb(NORelated literature
For the L ligands, see: Xian et al. (2008). For a related terbium(III) complex, see: Zhao et al. (2007
). For the zigzag chain cadmium(II) complex bridged by chloride, see: Li et al. (2008
). For iron(III) and cobalt(III) complexes of some N-salicylideneamino acids, see: Burrows & Bailar (1966
). For a heterodimetallic (Yb, La) complex, see: Costes et al. (1998
). For the syntheses of rare earth complexes with derived from o-vanillin and adamantaneamine, see: Zhao et al. (2005
).
Experimental
Crystal data
|
Refinement
|
|
|
Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006
); 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: SHELXL97 and PLATON (Spek, 2009
).
Supporting information
https://doi.org/10.1107/S1600536809041361/si2199sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041361/si2199Isup2.hkl
Reagents and solvents used were of commercially available quality and without purified before using. The Schiff base ligand 2-[(4- methylphenyl)iminomethyl]-6-methoxy-phenol was prepared by condensation of o-vanillin and p-methylaniline with a high yield and which was purified by recrystallization in ethanol. The compound (1) was obtained by adding Yb(NO3)3 (1 mmol, dissolved in methanol) to N-salicylidene-p-toluidine (3 mmol) in methanol solution. The mixture solution was stirred at room temperature for 8 h to obtain a purplish red solution. At last, the deposit was filtered out and the solution was kept for evaporating. The red crystal was formed after several days.
The structure was solved by
and successive Fourier difference synthesis. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å, Uiso(H) = 1.5Ueq(C), aromatic C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C), and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(N)]. The H atoms bonded to water O atoms were located in difference Fourier maps and refined with O—H distance restraints of 0.88 (2) and Uiso(H) = 1.5Ueq(O).It has well been confirmed that
are important in multiple fields such as chemistry and biochemistry owing to their biological activities (Zhao et al., 2005). Schiff base complexes prepared by ligands from substituted o-vanillin have been absorbed considerable attention in the past decades due to the intriguing biological activities of o-vanillin and the convenience in synthesis (Burrows & Bailar, 1966). Interested in this field, we have been engaged in a major effort directed toward the development of syntheses of new analogous derived from o-vanillin and their rare metal complexes. In a few of articles we have reported our partial research results (Zhao et al., 2007; Xian et al. 2008; Li et al. 2008). Herein, we describe a new ytterbium(III) complex.The structure of the title complex is shown in Fig.1, and the coordination environment of YbIII is shown in Fig. 2. In this complex the YbIII is eight-coordinated by O atoms, six of which come from three nitrate ions and two come from the Schiff base ligands (HL). The HL ligands coordinate to the YbIII ion using oxygen atoms from deprotonated phenolic hydroxyl groups. The ten Yb—O bond distances are listed in Table 1 (including weak Yb—O interactions). The distances between YbIII and methoxyl O atoms (2.833 (4) Å and 2.927 (3) Å for Yb—O2 and Yb—O4) are longer than in similar reported complexes (Costes et al., 1998; Zhao et al., 2007), and even longer than the distances between Yb and Nitrate N, indicating the interactions are weak. In contrast, in the TbIII complex Zhao (2007), the Tb—O (methoxyl) bonds are shorter and stronger (2.731 (2) Å and 2.744 (2) Å), which can be attribute to the ionic radii decrease from TbIII to YbIII due to the lanthanide contraction.
The hydrogen bonds and weak π···π non-covalent interactions lend stability to the structure. The hydrogen bonds are listed in Table 2 and the stacking plot of this compound is shown in Fig. 3. Complex molecules are linked in a chain through water molecules by hydrogen bonds, and different chains are interlocked with benzene rings of Schiff base using π···π stacking. In the HL ligands, the proton of the phenolic hydroxyl group is considered to have transferred to the N-imine atom, which involving in an intramolecular hydrogen bond (Table 2).
For the
of a zinc(II) complex with two chelating HL ligands, see: Xian et al. (2008). For a related terbium(III) complex, see: Zhao et al. (2007). For the zigzag chain cadmium(II) complex bridged by chloride, see: Li et al. (2008). For iron(III) and cobalt(III) complexes of some N-salicylideneamino acids, see: Burrows & Bailar (1966). For a heterodimetallic (Yb, La) complex, see: Costes et al. (1998). For the syntheses of rare earth complexes with derived from o-vanillin and adamantaneamine, see: Zhao et al. (2005).Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).[Yb(NO3)3(C15H15NO2)2]·H2O | Z = 2 |
Mr = 859.65 | F(000) = 858 |
Triclinic, P1 | Dx = 1.738 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6878 (1) Å | Cell parameters from 9270 reflections |
b = 9.9210 (2) Å | θ = 2.2–27.6° |
c = 18.5998 (3) Å | µ = 2.92 mm−1 |
α = 97.341 (1)° | T = 296 K |
β = 101.929 (1)° | Block, red |
γ = 106.593 (1)° | 0.27 × 0.16 × 0.10 mm |
V = 1642.63 (5) Å3 |
Bruker APEXII area-detector diffractometer | 7543 independent reflections |
Radiation source: fine-focus sealed tube | 6122 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 27.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.576, Tmax = 0.757 | k = −11→12 |
24571 measured reflections | l = −24→24 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.3718P] where P = (Fo2 + 2Fc2)/3 |
7543 reflections | (Δ/σ)max = 0.001 |
457 parameters | Δρmax = 1.88 e Å−3 |
4 restraints | Δρmin = −0.76 e Å−3 |
[Yb(NO3)3(C15H15NO2)2]·H2O | γ = 106.593 (1)° |
Mr = 859.65 | V = 1642.63 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6878 (1) Å | Mo Kα radiation |
b = 9.9210 (2) Å | µ = 2.92 mm−1 |
c = 18.5998 (3) Å | T = 296 K |
α = 97.341 (1)° | 0.27 × 0.16 × 0.10 mm |
β = 101.929 (1)° |
Bruker APEXII area-detector diffractometer | 7543 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6122 reflections with I > 2σ(I) |
Tmin = 0.576, Tmax = 0.757 | Rint = 0.029 |
24571 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 4 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 1.88 e Å−3 |
7543 reflections | Δρmin = −0.76 e Å−3 |
457 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
Yb | 0.968710 (17) | 0.805760 (19) | 0.249140 (10) | 0.04617 (8) | |
N1 | 1.4545 (4) | 1.0479 (4) | 0.27759 (19) | 0.0459 (8) | |
H1A | 1.3655 | 1.0118 | 0.2820 | 0.055* | |
N2 | 0.5165 (4) | 0.4795 (4) | 0.22488 (19) | 0.0456 (8) | |
H2A | 0.6045 | 0.5268 | 0.2226 | 0.055* | |
N3 | 0.8386 (5) | 0.7186 (5) | 0.0937 (2) | 0.0606 (10) | |
N4 | 1.1154 (5) | 0.7510 (6) | 0.3852 (3) | 0.0664 (12) | |
N5 | 0.9364 (6) | 1.0733 (5) | 0.2322 (3) | 0.0681 (12) | |
O1 | 1.2019 (3) | 0.8427 (3) | 0.24032 (17) | 0.0530 (8) | |
O2 | 1.0387 (3) | 0.5841 (4) | 0.1676 (2) | 0.0643 (9) | |
O3 | 0.7601 (3) | 0.7075 (3) | 0.28207 (17) | 0.0517 (7) | |
O4 | 0.8875 (3) | 0.9622 (4) | 0.36941 (19) | 0.0654 (9) | |
O5 | 0.7806 (3) | 0.6609 (4) | 0.14198 (19) | 0.0614 (9) | |
O6 | 0.9582 (4) | 0.8237 (4) | 0.12055 (19) | 0.0621 (8) | |
O7 | 0.7843 (6) | 0.6766 (5) | 0.0273 (2) | 0.0980 (14) | |
O8 | 1.1297 (5) | 0.8765 (5) | 0.3772 (2) | 0.0729 (10) | |
O9 | 1.0374 (4) | 0.6518 (4) | 0.3277 (2) | 0.0716 (10) | |
O10 | 1.1715 (5) | 0.7193 (5) | 0.4431 (2) | 0.0904 (13) | |
O11 | 0.8255 (4) | 0.9634 (4) | 0.2118 (2) | 0.0700 (9) | |
O12 | 1.0607 (4) | 1.0550 (3) | 0.2605 (2) | 0.0611 (9) | |
O13 | 0.9282 (6) | 1.1912 (5) | 0.2263 (3) | 0.1144 (18) | |
C1 | 1.3997 (4) | 0.8384 (5) | 0.1834 (2) | 0.0429 (9) | |
C2 | 1.2576 (4) | 0.7763 (5) | 0.1938 (2) | 0.0439 (9) | |
C3 | 1.1733 (5) | 0.6369 (5) | 0.1516 (2) | 0.0480 (10) | |
C4 | 1.2283 (5) | 0.5683 (5) | 0.1010 (3) | 0.0554 (11) | |
H4A | 1.1713 | 0.4774 | 0.0732 | 0.067* | |
C5 | 1.3693 (6) | 0.6341 (5) | 0.0912 (3) | 0.0600 (12) | |
H5A | 1.4049 | 0.5870 | 0.0563 | 0.072* | |
C6 | 1.4543 (5) | 0.7647 (5) | 0.1316 (2) | 0.0527 (11) | |
H6A | 1.5490 | 0.8065 | 0.1255 | 0.063* | |
C7 | 1.4944 (5) | 0.9742 (5) | 0.2276 (2) | 0.0467 (10) | |
H7A | 1.5889 | 1.0115 | 0.2203 | 0.056* | |
C8 | 0.9538 (7) | 0.4397 (6) | 0.1344 (4) | 0.092 (2) | |
H8A | 1.0138 | 0.3791 | 0.1452 | 0.139* | |
H8B | 0.9214 | 0.4305 | 0.0811 | 0.139* | |
H8C | 0.8685 | 0.4114 | 0.1544 | 0.139* | |
C9 | 1.5409 (5) | 1.1810 (4) | 0.3256 (2) | 0.0456 (9) | |
C10 | 1.6779 (5) | 1.2602 (5) | 0.3190 (3) | 0.0576 (11) | |
H10A | 1.7168 | 1.2282 | 0.2810 | 0.069* | |
C11 | 1.7572 (5) | 1.3869 (5) | 0.3689 (3) | 0.0619 (12) | |
H11A | 1.8502 | 1.4395 | 0.3643 | 0.074* | |
C12 | 1.7019 (6) | 1.4379 (5) | 0.4256 (3) | 0.0603 (12) | |
C13 | 1.5647 (6) | 1.3591 (6) | 0.4309 (3) | 0.0721 (15) | |
H13A | 1.5257 | 1.3921 | 0.4686 | 0.087* | |
C14 | 1.4825 (6) | 1.2312 (6) | 0.3812 (3) | 0.0673 (14) | |
H14A | 1.3888 | 1.1795 | 0.3853 | 0.081* | |
C15 | 1.7903 (7) | 1.5764 (6) | 0.4809 (3) | 0.0851 (18) | |
H15A | 1.7900 | 1.5618 | 0.5309 | 0.128* | |
H15B | 1.7462 | 1.6492 | 0.4705 | 0.128* | |
H15C | 1.8910 | 1.6061 | 0.4764 | 0.128* | |
C16 | 0.5417 (4) | 0.6699 (5) | 0.3259 (2) | 0.0442 (9) | |
C17 | 0.6855 (4) | 0.7534 (5) | 0.3255 (2) | 0.0424 (9) | |
C18 | 0.7486 (5) | 0.8889 (5) | 0.3747 (2) | 0.0481 (10) | |
C19 | 0.6746 (5) | 0.9362 (5) | 0.4222 (3) | 0.0569 (11) | |
H19A | 0.7185 | 1.0252 | 0.4544 | 0.068* | |
C20 | 0.5325 (6) | 0.8503 (6) | 0.4224 (3) | 0.0696 (15) | |
H20A | 0.4826 | 0.8825 | 0.4550 | 0.083* | |
C21 | 0.4670 (5) | 0.7214 (5) | 0.3758 (3) | 0.0602 (12) | |
H21A | 0.3720 | 0.6658 | 0.3762 | 0.072* | |
C22 | 0.4648 (5) | 0.5359 (5) | 0.2758 (2) | 0.0476 (10) | |
H22A | 0.3708 | 0.4851 | 0.2798 | 0.057* | |
C23 | 0.9660 (6) | 1.0991 (5) | 0.4183 (3) | 0.0681 (14) | |
H23A | 0.9765 | 1.0881 | 0.4695 | 0.102* | |
H23B | 0.9111 | 1.1644 | 0.4085 | 0.102* | |
H23C | 1.0628 | 1.1363 | 0.4097 | 0.102* | |
C24 | 0.4433 (4) | 0.3477 (4) | 0.1723 (2) | 0.0443 (9) | |
C25 | 0.3097 (5) | 0.2547 (5) | 0.1744 (3) | 0.0531 (11) | |
H25A | 0.2642 | 0.2759 | 0.2118 | 0.064* | |
C26 | 0.2433 (5) | 0.1309 (5) | 0.1216 (3) | 0.0589 (12) | |
H26A | 0.1524 | 0.0688 | 0.1235 | 0.071* | |
C27 | 0.3079 (6) | 0.0956 (5) | 0.0654 (3) | 0.0590 (12) | |
C28 | 0.4427 (6) | 0.1890 (6) | 0.0646 (3) | 0.0708 (14) | |
H28A | 0.4887 | 0.1667 | 0.0277 | 0.085* | |
C29 | 0.5122 (5) | 0.3158 (6) | 0.1174 (3) | 0.0628 (13) | |
H29A | 0.6033 | 0.3780 | 0.1158 | 0.075* | |
C30 | 0.2304 (5) | −0.0412 (5) | 0.0060 (3) | 0.0803 (16) | |
H30A | 0.1376 | −0.0919 | 0.0155 | 0.121* | |
H30B | 0.2930 | −0.1009 | 0.0077 | 0.121* | |
H30C | 0.2117 | −0.0171 | −0.0427 | 0.121* | |
O1W | 0.1609 (5) | 0.4096 (5) | 0.3221 (3) | 0.207 (4) | |
H1WB | 0.086 (11) | 0.330 (10) | 0.300 (8) | 0.310* | |
H1WA | 0.117 (14) | 0.466 (10) | 0.342 (5) | 0.310* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Yb | 0.03135 (10) | 0.04494 (13) | 0.05706 (13) | 0.00384 (8) | 0.01277 (8) | 0.00902 (9) |
N1 | 0.0345 (17) | 0.047 (2) | 0.050 (2) | 0.0088 (15) | 0.0070 (15) | 0.0024 (16) |
N2 | 0.0332 (17) | 0.049 (2) | 0.050 (2) | 0.0065 (15) | 0.0106 (15) | 0.0092 (16) |
N3 | 0.062 (3) | 0.061 (3) | 0.058 (3) | 0.026 (2) | 0.011 (2) | 0.002 (2) |
N4 | 0.056 (3) | 0.094 (4) | 0.062 (3) | 0.032 (3) | 0.027 (2) | 0.021 (3) |
N5 | 0.089 (3) | 0.061 (3) | 0.082 (3) | 0.039 (3) | 0.051 (3) | 0.029 (2) |
O1 | 0.0361 (15) | 0.061 (2) | 0.0549 (17) | 0.0093 (13) | 0.0141 (13) | −0.0023 (15) |
O2 | 0.0433 (17) | 0.055 (2) | 0.082 (2) | −0.0006 (15) | 0.0122 (16) | 0.0132 (18) |
O3 | 0.0392 (15) | 0.0500 (18) | 0.0610 (18) | 0.0054 (13) | 0.0213 (14) | 0.0007 (14) |
O4 | 0.0477 (18) | 0.059 (2) | 0.072 (2) | −0.0028 (15) | 0.0197 (16) | −0.0090 (17) |
O5 | 0.0461 (17) | 0.063 (2) | 0.064 (2) | 0.0046 (15) | 0.0174 (15) | −0.0037 (17) |
O6 | 0.062 (2) | 0.055 (2) | 0.066 (2) | 0.0109 (17) | 0.0205 (17) | 0.0134 (17) |
O7 | 0.130 (4) | 0.096 (3) | 0.050 (2) | 0.036 (3) | −0.003 (2) | −0.004 (2) |
O8 | 0.086 (3) | 0.077 (3) | 0.064 (2) | 0.042 (2) | 0.0200 (19) | 0.008 (2) |
O9 | 0.056 (2) | 0.069 (2) | 0.089 (3) | 0.0118 (18) | 0.0153 (19) | 0.034 (2) |
O10 | 0.096 (3) | 0.136 (4) | 0.064 (2) | 0.064 (3) | 0.025 (2) | 0.042 (3) |
O11 | 0.058 (2) | 0.068 (2) | 0.091 (3) | 0.0236 (19) | 0.0271 (19) | 0.019 (2) |
O12 | 0.059 (2) | 0.0428 (18) | 0.087 (2) | 0.0130 (15) | 0.0361 (18) | 0.0134 (17) |
O13 | 0.159 (5) | 0.073 (3) | 0.159 (5) | 0.065 (3) | 0.085 (4) | 0.056 (3) |
C1 | 0.0340 (19) | 0.048 (2) | 0.046 (2) | 0.0135 (18) | 0.0083 (17) | 0.0095 (19) |
C2 | 0.037 (2) | 0.050 (3) | 0.043 (2) | 0.0160 (18) | 0.0060 (17) | 0.0066 (19) |
C3 | 0.039 (2) | 0.050 (3) | 0.050 (2) | 0.0103 (19) | 0.0054 (18) | 0.011 (2) |
C4 | 0.062 (3) | 0.041 (3) | 0.055 (3) | 0.013 (2) | 0.005 (2) | 0.002 (2) |
C5 | 0.068 (3) | 0.059 (3) | 0.057 (3) | 0.027 (3) | 0.020 (2) | 0.002 (2) |
C6 | 0.048 (2) | 0.060 (3) | 0.052 (3) | 0.021 (2) | 0.017 (2) | 0.005 (2) |
C7 | 0.039 (2) | 0.052 (3) | 0.047 (2) | 0.0164 (19) | 0.0076 (18) | 0.003 (2) |
C8 | 0.069 (4) | 0.052 (3) | 0.143 (6) | −0.001 (3) | 0.019 (4) | 0.031 (4) |
C9 | 0.044 (2) | 0.040 (2) | 0.047 (2) | 0.0105 (18) | 0.0046 (18) | 0.0055 (19) |
C10 | 0.049 (3) | 0.053 (3) | 0.068 (3) | 0.010 (2) | 0.020 (2) | 0.007 (2) |
C11 | 0.051 (3) | 0.045 (3) | 0.077 (3) | 0.001 (2) | 0.011 (2) | 0.007 (2) |
C12 | 0.063 (3) | 0.043 (3) | 0.060 (3) | 0.006 (2) | −0.003 (2) | 0.011 (2) |
C13 | 0.082 (4) | 0.055 (3) | 0.067 (3) | 0.009 (3) | 0.026 (3) | −0.010 (3) |
C14 | 0.060 (3) | 0.055 (3) | 0.075 (3) | 0.003 (2) | 0.025 (3) | −0.004 (3) |
C15 | 0.098 (5) | 0.049 (3) | 0.076 (4) | 0.003 (3) | −0.004 (3) | −0.007 (3) |
C16 | 0.042 (2) | 0.046 (2) | 0.048 (2) | 0.0147 (18) | 0.0151 (18) | 0.0130 (19) |
C17 | 0.037 (2) | 0.047 (2) | 0.045 (2) | 0.0138 (18) | 0.0128 (17) | 0.0111 (19) |
C18 | 0.044 (2) | 0.050 (3) | 0.049 (2) | 0.0122 (19) | 0.0130 (19) | 0.009 (2) |
C19 | 0.059 (3) | 0.050 (3) | 0.064 (3) | 0.020 (2) | 0.020 (2) | 0.006 (2) |
C20 | 0.073 (3) | 0.062 (3) | 0.083 (4) | 0.022 (3) | 0.046 (3) | 0.003 (3) |
C21 | 0.052 (3) | 0.060 (3) | 0.076 (3) | 0.017 (2) | 0.036 (2) | 0.011 (3) |
C22 | 0.041 (2) | 0.045 (2) | 0.057 (3) | 0.0079 (18) | 0.0181 (19) | 0.017 (2) |
C23 | 0.060 (3) | 0.054 (3) | 0.070 (3) | 0.000 (2) | 0.008 (2) | −0.004 (3) |
C24 | 0.043 (2) | 0.039 (2) | 0.048 (2) | 0.0096 (18) | 0.0101 (18) | 0.0102 (18) |
C25 | 0.049 (2) | 0.049 (3) | 0.055 (3) | 0.004 (2) | 0.017 (2) | 0.009 (2) |
C26 | 0.051 (3) | 0.051 (3) | 0.065 (3) | 0.001 (2) | 0.015 (2) | 0.015 (2) |
C27 | 0.061 (3) | 0.052 (3) | 0.056 (3) | 0.014 (2) | 0.004 (2) | 0.011 (2) |
C28 | 0.064 (3) | 0.070 (4) | 0.076 (3) | 0.014 (3) | 0.029 (3) | 0.002 (3) |
C29 | 0.045 (3) | 0.061 (3) | 0.076 (3) | 0.007 (2) | 0.025 (2) | 0.001 (3) |
C30 | 0.083 (4) | 0.060 (3) | 0.077 (4) | 0.012 (3) | 0.001 (3) | −0.004 (3) |
O1W | 0.172 (7) | 0.191 (9) | 0.248 (10) | 0.041 (6) | 0.078 (7) | 0.018 (7) |
Yb—O3 | 2.225 (3) | C8—H8B | 0.9600 |
Yb—O1 | 2.228 (3) | C8—H8C | 0.9600 |
Yb—O12 | 2.342 (3) | C9—C10 | 1.375 (6) |
Yb—O5 | 2.373 (3) | C9—C14 | 1.383 (6) |
Yb—O9 | 2.379 (4) | C10—C11 | 1.373 (6) |
Yb—O6 | 2.404 (3) | C10—H10A | 0.9300 |
Yb—O11 | 2.444 (4) | C11—C12 | 1.382 (7) |
Yb—O8 | 2.451 (4) | C11—H11A | 0.9300 |
Yb—N5 | 2.809 (5) | C12—C13 | 1.367 (7) |
Yb—N3 | 2.815 (4) | C12—C15 | 1.510 (7) |
Yb—O2 | 2.833 (4) | C13—C14 | 1.384 (7) |
Yb—O4 | 2.927 (3) | C13—H13A | 0.9300 |
Yb—N4 | 2.833 (5) | C14—H14A | 0.9300 |
N1—C7 | 1.298 (5) | C15—H15A | 0.9600 |
N1—C9 | 1.414 (5) | C15—H15B | 0.9600 |
N1—H1A | 0.8600 | C15—H15C | 0.9600 |
N2—C22 | 1.297 (5) | C16—C17 | 1.405 (5) |
N2—C24 | 1.423 (5) | C16—C21 | 1.419 (6) |
N2—H2A | 0.8600 | C16—C22 | 1.423 (6) |
N3—O7 | 1.205 (5) | C17—C18 | 1.416 (6) |
N3—O5 | 1.267 (5) | C18—C19 | 1.365 (6) |
N3—O6 | 1.271 (5) | C19—C20 | 1.397 (7) |
N4—O10 | 1.223 (6) | C19—H19A | 0.9300 |
N4—O8 | 1.245 (6) | C20—C21 | 1.347 (7) |
N4—O9 | 1.287 (6) | C20—H20A | 0.9300 |
N5—O13 | 1.212 (6) | C21—H21A | 0.9300 |
N5—O11 | 1.242 (6) | C22—H22A | 0.9300 |
N5—O12 | 1.284 (6) | C23—H23A | 0.9600 |
O1—C2 | 1.313 (5) | C23—H23B | 0.9600 |
O2—C3 | 1.369 (5) | C23—H23C | 0.9600 |
O2—C8 | 1.415 (6) | C24—C25 | 1.369 (5) |
O3—C17 | 1.310 (5) | C24—C29 | 1.381 (6) |
O4—C18 | 1.365 (5) | C25—C26 | 1.367 (6) |
O4—C23 | 1.435 (5) | C25—H25A | 0.9300 |
C1—C2 | 1.402 (5) | C26—C27 | 1.381 (7) |
C1—C6 | 1.412 (6) | C26—H26A | 0.9300 |
C1—C7 | 1.425 (6) | C27—C28 | 1.373 (7) |
C2—C3 | 1.417 (6) | C27—C30 | 1.524 (7) |
C3—C4 | 1.372 (6) | C28—C29 | 1.388 (7) |
C4—C5 | 1.397 (7) | C28—H28A | 0.9300 |
C4—H4A | 0.9300 | C29—H29A | 0.9300 |
C5—C6 | 1.344 (6) | C30—H30A | 0.9600 |
C5—H5A | 0.9300 | C30—H30B | 0.9600 |
C6—H6A | 0.9300 | C30—H30C | 0.9600 |
C7—H7A | 0.9300 | O1W—H1WB | 0.88 |
C8—H8A | 0.9600 | O1W—H1WA | 0.88 |
O3—Yb—O1 | 157.78 (13) | C2—C1—C6 | 120.7 (4) |
O3—Yb—O12 | 119.91 (11) | C2—C1—C7 | 120.5 (4) |
O1—Yb—O12 | 77.05 (11) | C6—C1—C7 | 118.7 (4) |
O3—Yb—O5 | 70.20 (11) | O1—C2—C1 | 122.4 (4) |
O1—Yb—O5 | 115.39 (10) | O1—C2—C3 | 120.0 (4) |
O12—Yb—O5 | 120.65 (13) | C1—C2—C3 | 117.6 (4) |
O3—Yb—O9 | 77.22 (12) | O2—C3—C4 | 126.4 (4) |
O1—Yb—O9 | 80.67 (12) | O2—C3—C2 | 113.0 (4) |
O12—Yb—O9 | 131.26 (14) | C4—C3—C2 | 120.6 (4) |
O5—Yb—O9 | 108.04 (14) | C3—C4—C5 | 120.4 (4) |
O3—Yb—O6 | 119.78 (11) | C3—C4—H4A | 119.8 |
O1—Yb—O6 | 75.37 (11) | C5—C4—H4A | 119.8 |
O12—Yb—O6 | 79.10 (12) | C6—C5—C4 | 120.8 (4) |
O5—Yb—O6 | 53.28 (11) | C6—C5—H5A | 119.6 |
O9—Yb—O6 | 135.12 (13) | C4—C5—H5A | 119.6 |
O3—Yb—O11 | 78.88 (12) | C5—C6—C1 | 119.9 (4) |
O1—Yb—O11 | 123.06 (12) | C5—C6—H6A | 120.0 |
O12—Yb—O11 | 53.16 (12) | C1—C6—H6A | 120.0 |
O5—Yb—O11 | 76.57 (13) | N1—C7—C1 | 122.9 (4) |
O9—Yb—O11 | 152.18 (13) | N1—C7—H7A | 118.6 |
O6—Yb—O11 | 70.21 (12) | C1—C7—H7A | 118.6 |
O3—Yb—O8 | 95.26 (13) | O2—C8—H8A | 109.5 |
O1—Yb—O8 | 72.75 (12) | O2—C8—H8B | 109.5 |
O12—Yb—O8 | 79.24 (14) | H8A—C8—H8B | 109.5 |
O5—Yb—O8 | 159.19 (15) | O2—C8—H8C | 109.5 |
O9—Yb—O8 | 52.78 (14) | H8A—C8—H8C | 109.5 |
O6—Yb—O8 | 144.64 (13) | H8B—C8—H8C | 109.5 |
O11—Yb—O8 | 116.21 (13) | C10—C9—C14 | 119.7 (4) |
O3—Yb—N5 | 99.59 (12) | C10—C9—N1 | 123.0 (4) |
O1—Yb—N5 | 100.65 (13) | C14—C9—N1 | 117.3 (4) |
O12—Yb—N5 | 26.97 (13) | C11—C10—C9 | 119.8 (4) |
O5—Yb—N5 | 98.56 (14) | C11—C10—H10A | 120.1 |
O9—Yb—N5 | 149.93 (15) | C9—C10—H10A | 120.1 |
O6—Yb—N5 | 72.70 (12) | C10—C11—C12 | 121.5 (4) |
O11—Yb—N5 | 26.20 (13) | C10—C11—H11A | 119.3 |
O8—Yb—N5 | 98.52 (15) | C12—C11—H11A | 119.3 |
O3—Yb—N3 | 95.23 (12) | C13—C12—C11 | 118.2 (4) |
O1—Yb—N3 | 95.27 (12) | C13—C12—C15 | 120.6 (5) |
O12—Yb—N3 | 100.83 (13) | C11—C12—C15 | 121.3 (5) |
O5—Yb—N3 | 26.55 (11) | C12—C13—C14 | 121.5 (5) |
O9—Yb—N3 | 124.08 (14) | C12—C13—H13A | 119.3 |
O6—Yb—N3 | 26.74 (11) | C14—C13—H13A | 119.3 |
O11—Yb—N3 | 72.08 (12) | C9—C14—C13 | 119.4 (5) |
O8—Yb—N3 | 167.78 (12) | C9—C14—H14A | 120.3 |
N5—Yb—N3 | 85.88 (13) | C13—C14—H14A | 120.3 |
O3—Yb—O2 | 108.26 (10) | C12—C15—H15A | 109.5 |
O1—Yb—O2 | 60.78 (10) | C12—C15—H15B | 109.5 |
O12—Yb—O2 | 130.25 (10) | H15A—C15—H15B | 109.5 |
O5—Yb—O2 | 63.94 (11) | C12—C15—H15C | 109.5 |
O9—Yb—O2 | 68.91 (13) | H15A—C15—H15C | 109.5 |
O6—Yb—O2 | 66.31 (11) | H15B—C15—H15C | 109.5 |
O11—Yb—O2 | 133.11 (12) | C17—C16—C21 | 119.8 (4) |
O8—Yb—O2 | 109.30 (11) | C17—C16—C22 | 122.1 (4) |
N5—Yb—O2 | 137.96 (11) | C21—C16—C22 | 118.0 (4) |
N3—Yb—O2 | 61.23 (11) | O3—C17—C16 | 121.6 (4) |
O3—Yb—N4 | 85.22 (12) | O3—C17—C18 | 120.8 (3) |
O1—Yb—N4 | 75.93 (11) | C16—C17—C18 | 117.5 (4) |
O12—Yb—N4 | 105.01 (15) | C19—C18—O4 | 125.4 (4) |
O5—Yb—N4 | 134.23 (15) | C19—C18—C17 | 121.6 (4) |
O9—Yb—N4 | 26.82 (13) | O4—C18—C17 | 113.0 (4) |
O6—Yb—N4 | 149.20 (11) | C18—C19—C20 | 119.8 (4) |
O11—Yb—N4 | 136.87 (13) | C18—C19—H19A | 120.1 |
O8—Yb—N4 | 25.98 (13) | C20—C19—H19A | 120.1 |
N5—Yb—N4 | 123.86 (15) | C21—C20—C19 | 120.8 (4) |
N3—Yb—N4 | 149.85 (14) | C21—C20—H20A | 119.6 |
O2—Yb—N4 | 89.92 (12) | C19—C20—H20A | 119.6 |
C7—N1—C9 | 127.4 (4) | C20—C21—C16 | 120.4 (4) |
C7—N1—H1A | 116.3 | C20—C21—H21A | 119.8 |
C9—N1—H1A | 116.3 | C16—C21—H21A | 119.8 |
C22—N2—C24 | 127.0 (3) | N2—C22—C16 | 124.6 (4) |
C22—N2—H2A | 116.5 | N2—C22—H22A | 117.7 |
C24—N2—H2A | 116.5 | C16—C22—H22A | 117.7 |
O7—N3—O5 | 122.4 (5) | O4—C23—H23A | 109.5 |
O7—N3—O6 | 122.6 (5) | O4—C23—H23B | 109.5 |
O5—N3—O6 | 115.1 (4) | H23A—C23—H23B | 109.5 |
O7—N3—Yb | 177.5 (4) | O4—C23—H23C | 109.5 |
O5—N3—Yb | 56.8 (2) | H23A—C23—H23C | 109.5 |
O6—N3—Yb | 58.3 (2) | H23B—C23—H23C | 109.5 |
O10—N4—O8 | 123.9 (5) | C25—C24—C29 | 120.2 (4) |
O10—N4—O9 | 120.0 (5) | C25—C24—N2 | 122.6 (4) |
O8—N4—O9 | 116.0 (4) | C29—C24—N2 | 117.2 (4) |
O10—N4—Yb | 175.9 (4) | C26—C25—C24 | 120.0 (4) |
O8—N4—Yb | 59.6 (3) | C26—C25—H25A | 120.0 |
O9—N4—Yb | 56.5 (2) | C24—C25—H25A | 120.0 |
O13—N5—O11 | 122.2 (5) | C25—C26—C27 | 121.6 (4) |
O13—N5—O12 | 121.7 (5) | C25—C26—H26A | 119.2 |
O11—N5—O12 | 116.1 (4) | C27—C26—H26A | 119.2 |
O13—N5—Yb | 177.5 (5) | C28—C27—C26 | 117.7 (5) |
O11—N5—Yb | 60.3 (2) | C28—C27—C30 | 121.5 (5) |
O12—N5—Yb | 55.8 (2) | C26—C27—C30 | 120.8 (4) |
C2—O1—Yb | 131.5 (3) | C27—C28—C29 | 121.9 (5) |
C3—O2—C8 | 117.1 (4) | C27—C28—H28A | 119.1 |
C3—O2—Yb | 110.7 (3) | C29—C28—H28A | 119.1 |
C8—O2—Yb | 131.7 (3) | C24—C29—C28 | 118.6 (4) |
C17—O3—Yb | 135.2 (3) | C24—C29—H29A | 120.7 |
C18—O4—C23 | 118.6 (4) | C28—C29—H29A | 120.7 |
C18—O4—Yb | 110.7 (2) | C27—C30—H30A | 109.5 |
C23—O4—Yb | 130.7 (3) | C27—C30—H30B | 109.5 |
N3—O5—Yb | 96.6 (3) | H30A—C30—H30B | 109.5 |
N3—O6—Yb | 95.0 (3) | C27—C30—H30C | 109.5 |
N4—O8—Yb | 94.4 (3) | H30A—C30—H30C | 109.5 |
N4—O9—Yb | 96.7 (3) | H30B—C30—H30C | 109.5 |
N5—O11—Yb | 93.5 (3) | H1WB—O1W—H1WA | 103 |
N5—O12—Yb | 97.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 1.89 | 2.590 (4) | 138 |
N2—H2A···O3 | 0.86 | 1.99 | 2.668 (4) | 135 |
O1W—H1WB···O13i | 0.88 | 1.89 (13) | 2.7413 | 162 |
O1W—H1WB···N5i | 0.88 | 2.55 (11) | 3.4036 | 163 |
O1W—H1WA···O9ii | 0.88 | 2.22 (11) | 2.9742 | 144 |
C22—H22A···O1W | 0.93 | 2.29 | 3.1932 | 163 |
C4—H4A···O7iii | 0.93 | 2.45 | 3.137 (7) | 131 |
Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Yb(NO3)3(C15H15NO2)2]·H2O |
Mr | 859.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.6878 (1), 9.9210 (2), 18.5998 (3) |
α, β, γ (°) | 97.341 (1), 101.929 (1), 106.593 (1) |
V (Å3) | 1642.63 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.92 |
Crystal size (mm) | 0.27 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.576, 0.757 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24571, 7543, 6122 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.652 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.095, 0.99 |
No. of reflections | 7543 |
No. of parameters | 457 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.88, −0.76 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Yb—O3 | 2.225 (3) | Yb—O6 | 2.404 (3) |
Yb—O1 | 2.228 (3) | Yb—O11 | 2.444 (4) |
Yb—O12 | 2.342 (3) | Yb—O8 | 2.451 (4) |
Yb—O5 | 2.373 (3) | Yb—O2 | 2.833 (4) |
Yb—O9 | 2.379 (4) | Yb—O4 | 2.927 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 1.89 | 2.590 (4) | 137.6 |
N2—H2A···O3 | 0.86 | 1.99 | 2.668 (4) | 134.6 |
O1W—H1WB···O13i | 0.88 | 1.89 (13) | 2.74133 | 162 |
O1W—H1WB···N5i | 0.88 | 2.55 (11) | 3.40359 | 163 |
O1W—H1WA···O9ii | 0.88 | 2.22 (11) | 2.97416 | 144 |
C22—H22A···O1W | 0.93 | 2.29 | 3.1932 | 163 |
C4—H4A···O7iii | 0.93 | 2.45 | 3.137 (7) | 131 |
Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y, z; (iii) −x+2, −y+1, −z. |
References
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burrows, R. C. & Bailar, J. C. (1966). J. Am. Chem. Soc. 88, 4150–4152. CrossRef CAS Web of Science Google Scholar
Costes, J. P., Dahan, F., Dupuis, A., Lagrave, S. & Laurent, J. P. (1998). Inorg. Chem. 37, 153–155. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268. CSD CrossRef IUCr Journals Google Scholar
Zhao, G.-L., Zhang, P.-H. & Feng, Y.-L. (2005). Chin. J. Inorg. Chem. 21, 421–424. CAS 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.
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It has well been confirmed that Schiff bases are important in multiple fields such as chemistry and biochemistry owing to their biological activities (Zhao et al., 2005). Schiff base complexes prepared by ligands from substituted o-vanillin have been absorbed considerable attention in the past decades due to the intriguing biological activities of o-vanillin and the convenience in Schiff bases synthesis (Burrows & Bailar, 1966). Interested in this field, we have been engaged in a major effort directed toward the development of syntheses of new analogous Schiff bases derived from o-vanillin and their rare metal complexes. In a few of articles we have reported our partial research results (Zhao et al., 2007; Xian et al. 2008; Li et al. 2008). Herein, we describe a new ytterbium(III) complex.
The structure of the title complex is shown in Fig.1, and the coordination environment of YbIII is shown in Fig. 2. In this complex the YbIII is eight-coordinated by O atoms, six of which come from three nitrate ions and two come from the Schiff base ligands (HL). The HL ligands coordinate to the YbIII ion using oxygen atoms from deprotonated phenolic hydroxyl groups. The ten Yb—O bond distances are listed in Table 1 (including weak Yb—O interactions). The distances between YbIII and methoxyl O atoms (2.833 (4) Å and 2.927 (3) Å for Yb—O2 and Yb—O4) are longer than in similar reported complexes (Costes et al., 1998; Zhao et al., 2007), and even longer than the distances between Yb and Nitrate N, indicating the interactions are weak. In contrast, in the TbIII complex Zhao (2007), the Tb—O (methoxyl) bonds are shorter and stronger (2.731 (2) Å and 2.744 (2) Å), which can be attribute to the ionic radii decrease from TbIII to YbIII due to the lanthanide contraction.
The hydrogen bonds and weak π···π non-covalent interactions lend stability to the structure. The hydrogen bonds are listed in Table 2 and the stacking plot of this compound is shown in Fig. 3. Complex molecules are linked in a chain through water molecules by hydrogen bonds, and different chains are interlocked with benzene rings of Schiff base using π···π stacking. In the HL ligands, the proton of the phenolic hydroxyl group is considered to have transferred to the N-imine atom, which involving in an intramolecular hydrogen bond (Table 2).