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In the crystal structure of the title compound, [Yb(C36H38N4O4)]ClO4·CH3CN, the ytterbium ion is eight-coordinated and deeply buried in the cavity of the dianionic Schiff base ligand. The coordination polyhedron may be described as a distorted square anti­prism that shows a twist angle of 29.5 (1)° between the two square planes. The receptor adopts a syn arrangement, with both pendent arms on the same side of the crown group, and there are two helicities (one associated with this layout of the pendent arms and the other with the conformation of the crown ring), which give rise to enantiomeric pairs of diastereoisomers, viz. [Delta]([lambda][lambda][lambda][lambda]) and [Lambda]([delta][delta][delta][delta]).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106023833/ob3011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106023833/ob3011Isup2.hkl
Contains datablock I

CCDC reference: 618644

Comment top

Recently, we described the coordination ability of the dianionic Schiff base bibrachial lariat ether N,N'-bis-(2-salicylaldiminatebenzyl)-4,10-diaza-12-crown-4 (H2L) toward lanthanide(III) ions (González-Lorenzo et al., 2005). We have found that this receptor shows a certain degree of selectivity toward the heaviest lanthanide(III) ions, only forming stable complexes with lanthanides from LuIII to HoIII. Moreover, the luminescence properties of the corresponding YbIII and ErIII complexes make them ideally suited for use as luminescent tags even in protic media. They have been shown to be emissive in the near-IR, and time-resolved studies revealed that the solvent is excluded from the inner coordination sphere in solution.

The crystal structures of [Ho(L)]ClO4, (II), and [Er(L)]ClO4·H2O, (III), were reported previously (González-Lorenzo et al., 2005). We describe here the crystal structure of the title compound (I), which is the corresponding ytterbium complex, [Yb(L)]ClO4·CH3CN. Some examples of X-ray crystal structures of YbIII complexes with Schiff base ligands have been found in the literature. In those systems, the Schiff base function is incorporated within an acyclic ligand (Liu & Ding, 1998), within a macrocyclic receptor (Casellato et al., 2000; Lisowski & Starinowick, 2003; Barge et al., 2005), in a podand (Costes et al., 1998; Bernhardt et al., 2001; Kanesato et al., 2004) or in a cryptand (Rodríguez-Cortiñas et al., 2002). The X-ray crystal structure here described is the first example of a YbIII complex with a lariat ether containing Schiff base pendent arms.

Although crystals of (II) and (III) are isostructural in space group P1, compound (I) crystallizes in the monoclinic space group P21/c. Figs. 1 and 2 show two different perspectives of the structure of the [Yb(L)]+ complex, while selected bond lengths and angles are given in Table 1. The structure of the complex in (I) is quite similar to those in (II) and (III) (González-Lorenzo et al., 2005). The YbIII ion is wrapped up in the Schiff base receptor, bound to its eight available donor atoms. The coordination environment of the metal may be described as a distorted square antiprism composed of two parallel pseudo-planes; atoms N1, O1, N4 and O4 define one of the pseudo-planes (the mean deviation from planarity is 0.21 Å), while atoms N2, O2, N3 and O3 define the other (the mean deviation from planarity is 0.10 Å). The angle between these two least-squares planes is 0.91 (4)°, with the ytterbium ion located 1.1343 (2) Å from the first plane and at 1.5809 (2) Å from the second. The twist angle between two square planes is 29.5 (1)°, showing a deformation of the coordination polyhedron from a square antiprism (ideal value 45°) toward a square prism (ideal value 0°).

Fig. 1 allows an appraisal of the conformation adopted by the bibrachial receptor. Both side arms are orientated on the same side of the crown ring, resulting in a syn conformation. Likewise, the lone pairs of both pivotal N atoms are directed into the receptor cavity in an endo--endo arrangement. In [Yb(L)]+, there are two helicities (one associated with this layout of the pendent arms and the other with the conformation of the crown moiety), which may give rise to two enantiomeric pairs of diastereoisomers. On the one hand, the coordination of the crown moiety donor atoms to the YbIII ion gives rise to five-membered chelate rings, Yb—N—C—C—O, adopting conformations that can be described as λ or δ. On the other hand, the syn conformation adopted by the receptor L leads to a chiral structure for the complex with two possible optical isomers, labeled Λ or Δ (see Fig. 2), depending on the skew form of the pendent arms (Jacques & Desreux, 1994). The title compound is a racemic mixture of Δ(λλλλ) and Λ(δδδδ).

The N2—C14—C13 and N3—C23—C24 angles, related to the fold of the pendant arms in the receptor, are 114.28 (17) and 114.81 (17)°, whereas the planes defined by the benzene rings intersect at 20.04 (6)°, and those formed by the phenol rings intersect at 54.81 (7)°. The benzene and phenol rings of the same pendant arm form angles of 70.98 (6) and 74.69 (7)°. The distances between the donor atoms give an idea about the shape and size of the receptor cavity. In (I), the pivotal N atoms are separated by 4.339 (3) Å, the imine N atoms by 4.042 (3) Å, and the phenolate O atoms by 3.182 (2) Å.

Experimental top

The synthesis of [Yb(L)]ClO4·H2O was described by González-Lorenzo et al. (2005). Crystals of (I) suitable for X-ray crystallography were grown by slow diffusion of diethyl ether into an acetonitrile solution of [Yb(L)]ClO4·H2O. During this process, the crystal solvent was replaced with acetonitrile.

Refinement top

The positions of all H atoms were calculated geometrically and a riding model was used in their refinement, with C—H distances of 0.93–0.97 Å, and with Uiso(H) values of 1.2Ueq(C), or 1.5Ueq(C) for the methyl group.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Front view of the [Yb(L)]+ cation, showing the Δ(λλλλ) isomer. Displacement ellipsoids are drawn at the 50% probability level, and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Top view of the [Yb(L)]+ cation, showing the optical isomers Λ (left) and Δ (right). Atoms labeled with an asterisk (*) are at the symmetry position (−x, −y, −z).
{4,10-Bis[2-(2-oxidobenzylideneamino-κ2N,O)benzyl]-1,7-dioxa-4,10- diazacyclododecane-κ4N4,N10,O1,O7}ytterbium(III) perchlorate acetonitrile solvate top
Crystal data top
[Yb(C36H38N4O4)]ClO4·C2H3NF(000) = 1820
Mr = 904.25Dx = 1.668 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1499 reflections
a = 11.901 (2) Åθ = 2.4–28.3°
b = 13.855 (3) ŵ = 2.73 mm1
c = 21.936 (4) ÅT = 100 K
β = 95.347 (3)°Prism, yellow
V = 3601.3 (12) Å30.48 × 0.3 × 0.26 mm
Z = 4
Data collection top
Siemens SMART CCD 1000
diffractometer
8961 independent reflections
Radiation source: fine-focus sealed tube7644 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.347, Tmax = 0.49k = 1818
65102 measured reflectionsl = 2829
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.020 w = 1/[σ2(Fo2) + (0.0135P)2 + 3.274P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.046(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.74 e Å3
8961 reflectionsΔρmin = 0.85 e Å3
479 parameters
Crystal data top
[Yb(C36H38N4O4)]ClO4·C2H3NV = 3601.3 (12) Å3
Mr = 904.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.901 (2) ŵ = 2.73 mm1
b = 13.855 (3) ÅT = 100 K
c = 21.936 (4) Å0.48 × 0.3 × 0.26 mm
β = 95.347 (3)°
Data collection top
Siemens SMART CCD 1000
diffractometer
8961 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7644 reflections with I > 2σ(I)
Tmin = 0.347, Tmax = 0.49Rint = 0.042
65102 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0200 restraints
wR(F2) = 0.046H-atom parameters constrained
S = 1.09Δρmax = 0.74 e Å3
8961 reflectionsΔρmin = 0.85 e Å3
479 parameters
Special details top

Experimental. Data were collected using a Bruker SMART 1000 CCD based diffractometer operating at 100.0 K. Data were measured using phi-omega scans of 0.3 degrees per frame for 5 s. A total of 1321 frames were collected. The first 50 frames were recollected at the end of the measurement.

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. The structure was solved by Patterson method and refined by full matrix least-squares on F2. Refinement converged with anisotropic displacement parameters for all non-hydrogen atoms. Minimum and maximum final electron density −0.847 and 0.738 e %A−3.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Yb10.185365 (7)0.227855 (6)0.423948 (4)0.01203 (3)
Cl10.45962 (5)0.01837 (4)0.17604 (2)0.02226 (11)
O10.21509 (13)0.21639 (10)0.52073 (7)0.0174 (3)
O20.38640 (13)0.25312 (11)0.44450 (7)0.0206 (3)
O30.17611 (13)0.32225 (10)0.33167 (6)0.0173 (3)
O40.04499 (12)0.17031 (10)0.36754 (7)0.0153 (3)
O50.51237 (17)0.07256 (14)0.19266 (9)0.0387 (5)
O60.50930 (17)0.09363 (14)0.21474 (9)0.0396 (5)
O70.47527 (18)0.04092 (15)0.11338 (8)0.0420 (5)
O80.34236 (15)0.01223 (15)0.18428 (10)0.0414 (5)
N10.18932 (15)0.05464 (13)0.44677 (8)0.0156 (4)
N20.30251 (15)0.15077 (12)0.34110 (8)0.0154 (4)
N30.24117 (15)0.40817 (12)0.44567 (8)0.0154 (4)
N40.01556 (15)0.30366 (12)0.45813 (8)0.0138 (3)
N50.6944 (2)0.2314 (2)0.52154 (13)0.0515 (7)
C10.26408 (18)0.15854 (15)0.56206 (10)0.0162 (4)
C20.32012 (19)0.19591 (17)0.61667 (10)0.0199 (5)
H20.32410.26230.62280.024*
C30.36895 (19)0.13442 (18)0.66094 (10)0.0217 (5)
H30.40870.16030.69560.026*
C40.3603 (2)0.03468 (18)0.65510 (11)0.0250 (5)
H40.39060.00560.68630.03*
C50.3064 (2)0.00346 (17)0.60241 (11)0.0231 (5)
H50.29970.07010.59830.028*
C60.26099 (18)0.05653 (15)0.55451 (10)0.0165 (4)
C70.21396 (18)0.01154 (15)0.49869 (10)0.0175 (4)
H70.20.05440.50.021*
C80.14262 (19)0.00465 (15)0.39686 (10)0.0163 (4)
C90.04046 (19)0.05215 (15)0.39962 (10)0.0191 (4)
H90.00360.04930.43510.023*
C100.0067 (2)0.10390 (16)0.34928 (11)0.0213 (5)
H100.07570.13490.35090.026*
C110.0491 (2)0.10933 (16)0.29671 (11)0.0214 (5)
H110.01820.14480.26330.026*
C120.15147 (19)0.06164 (15)0.29391 (10)0.0194 (4)
H120.18880.06570.25860.023*
C130.19836 (19)0.00792 (15)0.34357 (10)0.0170 (4)
C140.30998 (18)0.04256 (15)0.34117 (10)0.0178 (4)
H14A0.36030.02240.37620.021*
H14B0.34310.0220.30450.021*
C150.42074 (18)0.18684 (17)0.34832 (10)0.0188 (4)
H15A0.42410.25080.33050.023*
H15B0.46870.14430.3270.023*
C160.46220 (19)0.19073 (17)0.41514 (11)0.0217 (5)
H16A0.46230.12660.43290.026*
H16B0.53850.21610.42040.026*
C170.43637 (19)0.34324 (17)0.46477 (12)0.0243 (5)
H17A0.46880.3750.43110.029*
H17B0.49610.3320.49720.029*
C180.34592 (19)0.40589 (16)0.48793 (11)0.0205 (5)
H18A0.32820.3820.52750.025*
H18B0.37460.47110.49360.025*
C190.2614 (2)0.45552 (15)0.38707 (10)0.0197 (5)
H19A0.3350.4370.37540.024*
H19B0.26070.52510.39210.024*
C200.1715 (2)0.42626 (15)0.33761 (10)0.0208 (5)
H20A0.09780.4460.34850.025*
H20B0.1850.45680.29920.025*
C210.2286 (2)0.29069 (15)0.27867 (10)0.0190 (5)
H21A0.30130.32190.27760.023*
H21B0.18170.30810.24180.023*
C220.24382 (19)0.18249 (16)0.28166 (9)0.0174 (4)
H22A0.17040.15160.27580.021*
H22B0.28720.1620.24870.021*
C230.15747 (18)0.46822 (15)0.47492 (10)0.0155 (4)
H23A0.09640.48440.44420.019*
H23B0.19360.52810.48880.019*
C240.10815 (18)0.42136 (14)0.52833 (10)0.0155 (4)
C250.13158 (19)0.45613 (15)0.58748 (10)0.0191 (4)
H250.18380.50570.59490.023*
C260.0783 (2)0.41810 (16)0.63583 (10)0.0219 (5)
H260.09550.44150.67530.026*
C270.0005 (2)0.34531 (16)0.62493 (10)0.0213 (5)
H270.03830.32120.65690.026*
C280.02333 (19)0.30798 (15)0.56612 (10)0.0182 (4)
H280.0750.25790.55910.022*
C290.03092 (18)0.34538 (14)0.51810 (9)0.0148 (4)
C300.08784 (18)0.29927 (14)0.43383 (10)0.0150 (4)
H300.14230.32820.45550.018*
C310.12700 (18)0.25405 (14)0.37654 (10)0.0150 (4)
C320.23891 (18)0.27190 (16)0.35214 (10)0.0186 (4)
H320.28320.31470.37220.022*
C330.28417 (19)0.22737 (17)0.29932 (10)0.0206 (4)
H330.35730.24110.2830.025*
C340.21733 (19)0.16088 (16)0.27074 (10)0.0198 (5)
H340.24760.12890.23570.024*
C350.10798 (19)0.14192 (15)0.29340 (10)0.0177 (4)
H350.06590.09740.27340.021*
C360.05822 (17)0.18867 (15)0.34639 (9)0.0142 (4)
C370.6705 (2)0.2303 (2)0.57049 (13)0.0312 (6)
C380.6400 (3)0.2306 (2)0.63307 (13)0.0368 (6)
H38A0.70690.22420.66080.055*
H38B0.59010.17760.63880.055*
H38C0.60290.29020.6410.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Yb10.01257 (4)0.01168 (4)0.01154 (4)0.00042 (4)0.00045 (3)0.00012 (3)
C10.0148 (10)0.0206 (10)0.0134 (10)0.0027 (8)0.0032 (8)0.0024 (8)
C20.0221 (11)0.0224 (11)0.0152 (11)0.0006 (9)0.0022 (9)0.0009 (8)
C30.0180 (11)0.0341 (13)0.0128 (11)0.0018 (10)0.0005 (9)0.0008 (9)
C40.0262 (13)0.0325 (13)0.0161 (11)0.0085 (11)0.0002 (9)0.0060 (10)
C50.0265 (12)0.0212 (11)0.0214 (12)0.0045 (10)0.0008 (9)0.0033 (9)
C60.0163 (10)0.0186 (10)0.0145 (10)0.0022 (8)0.0010 (8)0.0027 (8)
C70.0180 (11)0.0138 (9)0.0208 (11)0.0019 (8)0.0024 (9)0.0019 (8)
C80.0208 (11)0.0122 (9)0.0153 (10)0.0024 (8)0.0011 (8)0.0002 (8)
C90.0222 (11)0.0155 (10)0.0198 (11)0.0003 (9)0.0024 (9)0.0009 (8)
C100.0214 (12)0.0167 (10)0.0255 (12)0.0029 (9)0.0005 (9)0.0004 (9)
C110.0262 (12)0.0149 (10)0.0216 (12)0.0005 (9)0.0047 (9)0.0030 (8)
C120.0245 (12)0.0162 (10)0.0174 (11)0.0032 (9)0.0020 (9)0.0008 (8)
C130.0186 (11)0.0142 (9)0.0179 (11)0.0036 (8)0.0006 (8)0.0001 (8)
C140.0177 (11)0.0165 (10)0.0192 (11)0.0029 (9)0.0019 (8)0.0015 (8)
C150.0129 (10)0.0210 (10)0.0228 (12)0.0002 (9)0.0038 (8)0.0015 (9)
C160.0128 (10)0.0248 (11)0.0270 (12)0.0028 (9)0.0011 (9)0.0051 (10)
C170.0160 (11)0.0225 (11)0.0329 (14)0.0025 (9)0.0055 (10)0.0044 (10)
C180.0182 (11)0.0180 (10)0.0241 (12)0.0019 (9)0.0050 (9)0.0029 (9)
C190.0237 (12)0.0147 (10)0.0213 (11)0.0020 (9)0.0053 (9)0.0030 (8)
C200.0316 (13)0.0135 (10)0.0172 (11)0.0027 (9)0.0031 (9)0.0030 (8)
C210.0223 (11)0.0210 (11)0.0142 (10)0.0034 (9)0.0035 (9)0.0010 (8)
C220.0188 (11)0.0207 (10)0.0126 (10)0.0032 (9)0.0006 (8)0.0015 (8)
C230.0173 (10)0.0129 (9)0.0159 (10)0.0013 (8)0.0001 (8)0.0014 (8)
C240.0169 (10)0.0132 (9)0.0159 (10)0.0027 (8)0.0004 (8)0.0002 (8)
C250.0231 (12)0.0143 (10)0.0189 (11)0.0003 (9)0.0039 (9)0.0025 (8)
C260.0312 (13)0.0197 (11)0.0137 (11)0.0063 (10)0.0031 (9)0.0023 (8)
C270.0309 (13)0.0191 (11)0.0144 (11)0.0051 (10)0.0045 (9)0.0020 (8)
C280.0226 (11)0.0140 (9)0.0181 (11)0.0009 (9)0.0017 (9)0.0000 (8)
C290.0170 (10)0.0130 (9)0.0139 (10)0.0033 (8)0.0004 (8)0.0019 (7)
C300.0177 (10)0.0117 (9)0.0159 (10)0.0013 (8)0.0034 (8)0.0005 (7)
C310.0153 (10)0.0147 (10)0.0151 (10)0.0010 (8)0.0016 (8)0.0011 (7)
C320.0162 (10)0.0181 (10)0.0214 (11)0.0012 (9)0.0015 (8)0.0002 (9)
C330.0154 (10)0.0230 (11)0.0220 (11)0.0006 (9)0.0046 (8)0.0011 (9)
C340.0197 (11)0.0222 (11)0.0163 (11)0.0033 (9)0.0041 (9)0.0007 (8)
C350.0194 (11)0.0174 (10)0.0160 (11)0.0000 (9)0.0007 (8)0.0029 (8)
C360.0153 (10)0.0135 (9)0.0138 (10)0.0006 (8)0.0008 (8)0.0022 (8)
C370.0188 (12)0.0362 (14)0.0372 (16)0.0060 (11)0.0041 (11)0.0033 (12)
C380.0392 (16)0.0353 (14)0.0361 (15)0.0079 (13)0.0042 (12)0.0040 (12)
Cl10.0185 (3)0.0308 (3)0.0169 (3)0.0073 (2)0.0012 (2)0.0020 (2)
N10.0176 (9)0.0148 (8)0.0143 (9)0.0003 (7)0.0014 (7)0.0012 (7)
N20.0144 (9)0.0156 (8)0.0161 (9)0.0014 (7)0.0011 (7)0.0006 (7)
N30.0165 (9)0.0152 (8)0.0142 (9)0.0009 (7)0.0007 (7)0.0005 (7)
N40.0171 (9)0.0112 (8)0.0128 (9)0.0012 (7)0.0005 (7)0.0012 (6)
N50.0293 (13)0.086 (2)0.0385 (16)0.0126 (14)0.0008 (11)0.0013 (14)
O10.0238 (8)0.0163 (7)0.0116 (7)0.0042 (6)0.0009 (6)0.0009 (6)
O20.0139 (7)0.0232 (8)0.0243 (9)0.0008 (6)0.0002 (6)0.0077 (6)
O30.0249 (8)0.0144 (7)0.0131 (7)0.0008 (6)0.0042 (6)0.0001 (6)
O40.0143 (7)0.0149 (7)0.0163 (7)0.0024 (6)0.0009 (6)0.0021 (6)
O50.0435 (12)0.0396 (11)0.0347 (11)0.0214 (9)0.0123 (9)0.0121 (9)
O60.0445 (12)0.0439 (12)0.0287 (10)0.0174 (10)0.0052 (9)0.0014 (8)
O70.0571 (13)0.0527 (12)0.0161 (9)0.0291 (11)0.0034 (9)0.0045 (8)
O80.0170 (9)0.0567 (13)0.0499 (13)0.0033 (9)0.0004 (8)0.0185 (10)
Geometric parameters (Å, º) top
Yb1—O12.1254 (15)C14—H14A0.97
Yb1—O42.1383 (14)C14—H14B0.97
Yb1—O32.4039 (15)C15—H15A0.97
Yb1—O22.4184 (16)C15—H15B0.97
Yb1—N12.4511 (18)C16—C151.503 (3)
Yb1—N42.4560 (18)C16—H16A0.97
Yb1—N32.6174 (18)C16—H16B0.97
Yb1—N22.6190 (18)C17—C181.507 (3)
Cl1—O81.4263 (19)C17—H17A0.97
Cl1—O61.4367 (19)C17—H17B0.97
Cl1—O71.4386 (19)C18—H18A0.97
Cl1—O51.4392 (19)C18—H18B0.97
O3—C211.438 (3)C19—H19A0.97
O3—C201.448 (2)C19—H19B0.97
O4—C361.297 (2)C20—C191.506 (3)
O2—C171.436 (3)C20—H20A0.97
O2—C161.444 (3)C20—H20B0.97
N1—C71.295 (3)C21—C221.511 (3)
N1—C81.438 (3)C21—H21A0.97
N2—C221.487 (3)C21—H21B0.97
N2—C151.488 (3)C22—H22A0.97
N2—C141.502 (3)C22—H22B0.97
N3—C191.483 (3)C23—H23A0.97
N3—C181.483 (3)C23—H23B0.97
N3—C231.488 (3)C24—C231.506 (3)
N4—C301.296 (3)C24—C251.388 (3)
N4—C291.433 (3)C24—C291.402 (3)
N5—C371.136 (4)C25—C261.389 (3)
C1—C21.414 (3)C25—H250.93
C1—O11.306 (2)C26—H260.93
C2—H20.93C27—C261.383 (3)
C3—C21.379 (3)C27—H270.93
C3—C41.391 (3)C28—C271.393 (3)
C3—H30.93C28—H280.93
C4—H40.93C29—C281.386 (3)
C5—C41.375 (3)C30—H300.93
C5—H50.93C31—C301.442 (3)
C6—C11.423 (3)C31—C361.424 (3)
C6—C51.407 (3)C32—C311.410 (3)
C6—C71.440 (3)C32—C331.377 (3)
C7—H70.93C32—H320.93
C8—C91.389 (3)C33—H330.93
C9—H90.93C34—C331.403 (3)
C10—C111.385 (3)C34—H340.93
C10—C91.391 (3)C35—C341.374 (3)
C10—H100.93C35—C361.412 (3)
C11—H110.93C35—H350.93
C12—C111.393 (3)C37—C381.452 (4)
C12—H120.93C38—H38A0.96
C13—C121.392 (3)C38—H38B0.96
C13—C141.507 (3)C38—H38C0.96
C13—C81.397 (3)
O1—Yb1—O4126.76 (6)C36—C31—C30121.86 (19)
O1—Yb1—O3150.70 (5)O1—C1—C2120.5 (2)
O1—Yb1—O275.81 (6)O1—C1—C6121.57 (19)
O1—Yb1—N174.01 (6)C2—C1—C6117.87 (19)
O1—Yb1—N478.00 (6)C29—C28—C27120.0 (2)
O1—Yb1—N382.75 (6)C29—C28—H28120
O1—Yb1—N2127.79 (6)C27—C28—H28120
O2—Yb1—N195.96 (6)C2—C3—C4121.8 (2)
O2—Yb1—N4135.16 (5)C2—C3—H3119.1
O2—Yb1—N366.30 (5)C4—C3—H3119.1
O2—Yb1—N266.86 (5)C3—C2—C1120.3 (2)
O3—Yb1—N1134.68 (5)C3—C2—H2119.8
O3—Yb1—O292.59 (5)C1—C2—H2119.8
O3—Yb1—N492.87 (5)O4—C36—C35121.00 (19)
O3—Yb1—N367.97 (5)O4—C36—C31121.64 (19)
O3—Yb1—N267.86 (5)C35—C36—C31117.33 (19)
O4—Yb1—O375.14 (5)C9—C8—C13120.5 (2)
O4—Yb1—O2150.21 (5)C9—C8—N1121.01 (19)
O4—Yb1—N175.65 (6)C13—C8—N1118.38 (19)
O4—Yb1—N473.47 (6)O2—C17—C18108.47 (18)
O4—Yb1—N3129.24 (5)O2—C17—H17A110
O4—Yb1—N283.34 (6)C18—C17—H17A110
N1—Yb1—N275.00 (6)O2—C17—H17B110
N1—Yb1—N3153.85 (6)C18—C17—H17B110
N1—Yb1—N4110.92 (6)H17A—C17—H17B108.4
N3—Yb1—N2111.91 (6)C13—C12—C11120.5 (2)
N4—Yb1—N2153.21 (6)C13—C12—H12119.8
N4—Yb1—N374.83 (6)C11—C12—H12119.8
O6—Cl1—O5109.87 (12)C10—C11—C12120.0 (2)
O6—Cl1—O7108.91 (13)C10—C11—H11120
O7—Cl1—O5109.87 (11)C12—C11—H11120
O8—Cl1—O5108.94 (13)O3—C20—C19107.61 (17)
O8—Cl1—O6108.79 (12)O3—C20—H20A110.2
O8—Cl1—O7110.45 (13)C19—C20—H20A110.2
C21—O3—C20113.46 (16)O3—C20—H20B110.2
C21—O3—Yb1121.74 (12)C19—C20—H20B110.2
C20—O3—Yb1117.68 (12)H20A—C20—H20B108.5
C36—O4—Yb1142.80 (13)N2—C14—C13114.28 (17)
C17—O2—C16113.63 (17)N2—C14—H14A108.7
C17—O2—Yb1123.90 (13)C13—C14—H14A108.7
C16—O2—Yb1118.59 (12)N2—C14—H14B108.7
C19—N3—C18110.87 (17)C13—C14—H14B108.7
C19—N3—C23107.21 (16)H14A—C14—H14B107.6
C18—N3—C23107.45 (16)N3—C19—C20110.08 (18)
C19—N3—Yb1108.88 (12)N3—C19—H19A109.6
C18—N3—Yb1106.13 (12)C20—C19—H19A109.6
C23—N3—Yb1116.32 (12)N3—C19—H19B109.6
C30—N4—C29115.57 (18)C20—C19—H19B109.6
C30—N4—Yb1129.12 (14)H19A—C19—H19B108.2
C29—N4—Yb1114.49 (13)C32—C33—C34118.5 (2)
C22—N2—C15110.88 (17)C32—C33—H33120.8
C22—N2—C14108.59 (16)C34—C33—H33120.8
C15—N2—C14106.26 (16)C24—C25—C26121.1 (2)
C22—N2—Yb1104.53 (12)C24—C25—H25119.5
C15—N2—Yb1110.39 (12)C26—C25—H25119.5
C14—N2—Yb1116.21 (12)N5—C37—C38179.1 (3)
C7—N1—C8116.47 (18)N1—C7—C6125.9 (2)
C7—N1—Yb1129.01 (14)N1—C7—H7117.1
C8—N1—Yb1113.89 (13)C6—C7—H7117.1
C34—C35—C36121.4 (2)N4—C30—C31126.6 (2)
C34—C35—H35119.3N4—C30—H30116.7
C36—C35—H35119.3C31—C30—H30116.7
C25—C24—C29118.8 (2)N2—C15—C16109.70 (18)
C25—C24—C23121.26 (19)N2—C15—H15A109.7
C29—C24—C23119.77 (19)C16—C15—H15A109.7
C5—C6—C1119.7 (2)N2—C15—H15B109.7
C5—C6—C7118.1 (2)C16—C15—H15B109.7
C1—C6—C7122.19 (19)H15A—C15—H15B108.2
C12—C13—C8119.0 (2)C26—C27—C28120.1 (2)
C12—C13—C14120.7 (2)C26—C27—H27119.9
C8—C13—C14120.20 (19)C28—C27—H27119.9
O3—C21—C22109.03 (17)C4—C5—C6121.2 (2)
O3—C21—H21A109.9C4—C5—H5119.4
C22—C21—H21A109.9C6—C5—H5119.4
O3—C21—H21B109.9N2—C22—C21112.09 (17)
C22—C21—H21B109.9N2—C22—H22A109.2
H21A—C21—H21B108.3C21—C22—H22A109.2
C35—C34—C33121.4 (2)N2—C22—H22B109.2
C35—C34—H34119.3C21—C22—H22B109.2
C33—C34—H34119.3H22A—C22—H22B107.9
C11—C10—C9120.0 (2)N3—C18—C17112.75 (18)
C11—C10—H10120N3—C18—H18A109
C9—C10—H10120C17—C18—H18A109
O2—C16—C15107.13 (18)N3—C18—H18B109
O2—C16—H16A110.3C17—C18—H18B109
C15—C16—H16A110.3H18A—C18—H18B107.8
O2—C16—H16B110.3C27—C26—C25119.7 (2)
C15—C16—H16B110.3C27—C26—H26120.2
H16A—C16—H16B108.5C25—C26—H26120.2
N3—C23—C24114.81 (17)C8—C9—C10120.0 (2)
N3—C23—H23A108.6C8—C9—H9120
C24—C23—H23A108.6C10—C9—H9120
N3—C23—H23B108.6C5—C4—C3119.0 (2)
C24—C23—H23B108.6C5—C4—H4120.5
H23A—C23—H23B107.5C3—C4—H4120.5
C28—C29—C24120.26 (19)C37—C38—H38A109.5
C28—C29—N4121.22 (19)C37—C38—H38B109.5
C24—C29—N4118.40 (19)H38A—C38—H38B109.5
C33—C32—C31121.5 (2)C37—C38—H38C109.5
C33—C32—H32119.3H38A—C38—H38C109.5
C31—C32—H32119.3H38B—C38—H38C109.5
C32—C31—C36119.91 (19)C1—O1—Yb1139.58 (13)
C32—C31—C30118.14 (19)
O1—Yb1—O3—C21132.58 (16)C20—O3—C21—C22172.06 (17)
O4—Yb1—O3—C2185.00 (15)Yb1—O3—C21—C2222.3 (2)
O2—Yb1—O3—C2167.47 (15)C36—C35—C34—C330.1 (3)
N1—Yb1—O3—C2133.54 (18)C17—O2—C16—C15110.3 (2)
N4—Yb1—O3—C21157.06 (15)Yb1—O2—C16—C1548.4 (2)
N3—Yb1—O3—C21130.57 (16)C19—N3—C23—C24167.93 (18)
N2—Yb1—O3—C213.77 (14)C18—N3—C23—C2472.8 (2)
O1—Yb1—O3—C2016.0 (2)Yb1—N3—C23—C2445.9 (2)
O4—Yb1—O3—C20126.44 (15)C25—C24—C23—N3112.4 (2)
O2—Yb1—O3—C2081.09 (15)C29—C24—C23—N372.1 (3)
N1—Yb1—O3—C20177.91 (13)C25—C24—C29—C281.9 (3)
N4—Yb1—O3—C2054.38 (15)C23—C24—C29—C28173.69 (19)
N3—Yb1—O3—C2017.98 (14)C25—C24—C29—N4173.97 (19)
N2—Yb1—O3—C20144.79 (16)C23—C24—C29—N410.4 (3)
O1—Yb1—O4—C3685.2 (2)C30—N4—C29—C2857.0 (3)
O3—Yb1—O4—C3673.0 (2)Yb1—N4—C29—C28113.64 (19)
O2—Yb1—O4—C36141.3 (2)C30—N4—C29—C24127.1 (2)
N1—Yb1—O4—C36142.1 (2)Yb1—N4—C29—C2462.2 (2)
N4—Yb1—O4—C3624.7 (2)C33—C32—C31—C360.0 (3)
N3—Yb1—O4—C3628.8 (2)C33—C32—C31—C30176.6 (2)
N2—Yb1—O4—C36141.8 (2)C5—C6—C1—O1174.5 (2)
O1—Yb1—O2—C1780.47 (17)C7—C6—C1—O16.3 (3)
O4—Yb1—O2—C17136.31 (16)C5—C6—C1—C24.2 (3)
O3—Yb1—O2—C1772.28 (17)C7—C6—C1—C2175.0 (2)
N1—Yb1—O2—C17152.29 (17)C24—C29—C28—C270.6 (3)
N4—Yb1—O2—C1724.4 (2)N4—C29—C28—C27175.2 (2)
N3—Yb1—O2—C177.74 (16)C4—C3—C2—C13.2 (3)
N2—Yb1—O2—C17136.84 (18)O1—C1—C2—C3178.2 (2)
O1—Yb1—O2—C16123.14 (16)C6—C1—C2—C30.5 (3)
O4—Yb1—O2—C1620.1 (2)Yb1—O4—C36—C35158.58 (17)
O3—Yb1—O2—C1684.11 (15)Yb1—O4—C36—C3123.5 (3)
N1—Yb1—O2—C1651.33 (16)C34—C35—C36—O4179.9 (2)
N4—Yb1—O2—C16179.21 (14)C34—C35—C36—C311.9 (3)
N3—Yb1—O2—C16148.65 (16)C32—C31—C36—O4179.85 (19)
N2—Yb1—O2—C1619.55 (14)C30—C31—C36—O43.4 (3)
O1—Yb1—N3—C19166.97 (14)C32—C31—C36—C351.9 (3)
O4—Yb1—N3—C1960.58 (15)C30—C31—C36—C35174.57 (19)
O3—Yb1—N3—C1914.03 (13)C12—C13—C8—C91.7 (3)
O2—Yb1—N3—C1989.32 (14)C14—C13—C8—C9179.12 (19)
N1—Yb1—N3—C19139.76 (15)C12—C13—C8—N1177.21 (19)
N4—Yb1—N3—C19113.56 (14)C14—C13—C8—N15.4 (3)
N2—Yb1—N3—C1939.04 (14)C7—N1—C8—C962.1 (3)
O1—Yb1—N3—C1847.57 (13)Yb1—N1—C8—C9109.68 (19)
O4—Yb1—N3—C18179.97 (12)C7—N1—C8—C13122.4 (2)
O3—Yb1—N3—C18133.42 (14)Yb1—N1—C8—C1365.8 (2)
O2—Yb1—N3—C1830.07 (13)C16—O2—C17—C18173.70 (19)
N1—Yb1—N3—C1820.4 (2)Yb1—O2—C17—C1816.3 (3)
N4—Yb1—N3—C18127.05 (14)C8—C13—C12—C111.7 (3)
N2—Yb1—N3—C1880.35 (14)C14—C13—C12—C11179.0 (2)
O1—Yb1—N3—C2371.85 (14)C9—C10—C11—C121.1 (3)
O4—Yb1—N3—C2360.61 (15)C13—C12—C11—C100.3 (3)
O3—Yb1—N3—C23107.16 (14)C21—O3—C20—C19104.0 (2)
O2—Yb1—N3—C23149.49 (15)Yb1—O3—C20—C1947.1 (2)
N1—Yb1—N3—C2399.05 (18)C22—N2—C14—C1369.2 (2)
N4—Yb1—N3—C237.63 (13)C15—N2—C14—C13171.48 (18)
N2—Yb1—N3—C23160.23 (13)Yb1—N2—C14—C1348.2 (2)
O1—Yb1—N4—C30142.47 (18)C12—C13—C14—N2112.8 (2)
O4—Yb1—N4—C307.94 (17)C8—C13—C14—N269.9 (3)
O3—Yb1—N4—C3065.64 (18)C18—N3—C19—C20159.37 (18)
O2—Yb1—N4—C30162.21 (16)C23—N3—C19—C2083.6 (2)
N1—Yb1—N4—C3074.97 (18)Yb1—N3—C19—C2042.98 (19)
N3—Yb1—N4—C30131.89 (18)O3—C20—C19—N359.4 (2)
N2—Yb1—N4—C3023.2 (2)C31—C32—C33—C341.9 (3)
O1—Yb1—N4—C2926.62 (13)C35—C34—C33—C321.8 (3)
O4—Yb1—N4—C29161.15 (14)C29—C24—C25—C261.2 (3)
O3—Yb1—N4—C29125.27 (14)C23—C24—C25—C26174.3 (2)
O2—Yb1—N4—C2928.70 (17)C8—N1—C7—C6179.8 (2)
N1—Yb1—N4—C2994.11 (14)Yb1—N1—C7—C69.5 (3)
N3—Yb1—N4—C2959.02 (13)C5—C6—C7—N1165.7 (2)
N2—Yb1—N4—C29167.72 (13)C1—C6—C7—N113.5 (3)
O1—Yb1—N2—C22179.98 (12)C29—N4—C30—C31174.71 (19)
O4—Yb1—N2—C2247.80 (13)Yb1—N4—C30—C315.7 (3)
O3—Yb1—N2—C2228.83 (12)C32—C31—C30—N4168.4 (2)
O2—Yb1—N2—C22131.94 (14)C36—C31—C30—N415.1 (3)
N1—Yb1—N2—C22124.68 (13)C22—N2—C15—C16156.85 (18)
N4—Yb1—N2—C2217.9 (2)C14—N2—C15—C1685.3 (2)
N3—Yb1—N2—C2281.96 (13)Yb1—N2—C15—C1641.5 (2)
O1—Yb1—N2—C1560.70 (15)O2—C16—C15—N258.2 (2)
O4—Yb1—N2—C15167.08 (14)C29—C28—C27—C261.6 (3)
O3—Yb1—N2—C1590.45 (14)C1—C6—C5—C44.2 (3)
O2—Yb1—N2—C1512.66 (12)C7—C6—C5—C4174.9 (2)
N1—Yb1—N2—C15116.04 (14)C15—N2—C22—C2165.8 (2)
N4—Yb1—N2—C15137.15 (14)C14—N2—C22—C21177.76 (17)
N3—Yb1—N2—C1537.33 (14)Yb1—N2—C22—C2153.11 (19)
O1—Yb1—N2—C1460.36 (16)O3—C21—C22—N252.1 (2)
O4—Yb1—N2—C1471.86 (14)C19—N3—C18—C1765.7 (2)
O3—Yb1—N2—C14148.48 (15)C23—N3—C18—C17177.41 (18)
O2—Yb1—N2—C14108.40 (14)Yb1—N3—C18—C1752.3 (2)
N1—Yb1—N2—C145.02 (13)O2—C17—C18—N346.9 (3)
N4—Yb1—N2—C14101.79 (17)C28—C27—C26—C252.3 (3)
N3—Yb1—N2—C14158.39 (13)C24—C25—C26—C270.9 (3)
O1—Yb1—N1—C76.33 (18)C13—C8—C9—C100.4 (3)
O4—Yb1—N1—C7142.05 (19)N1—C8—C9—C10175.8 (2)
O3—Yb1—N1—C7166.65 (16)C11—C10—C9—C81.0 (3)
O2—Yb1—N1—C767.04 (19)C6—C5—C4—C30.6 (4)
N4—Yb1—N1—C776.39 (19)C2—C3—C4—C53.2 (4)
N3—Yb1—N1—C721.8 (3)C2—C1—O1—Yb1144.29 (18)
N2—Yb1—N1—C7131.12 (19)C6—C1—O1—Yb137.1 (3)
O1—Yb1—N1—C8164.19 (15)O4—Yb1—O1—C189.1 (2)
O4—Yb1—N1—C828.47 (14)O3—Yb1—O1—C1138.3 (2)
O3—Yb1—N1—C822.83 (17)O2—Yb1—O1—C169.1 (2)
O2—Yb1—N1—C8122.44 (14)N1—Yb1—O1—C131.5 (2)
N4—Yb1—N1—C894.13 (14)N4—Yb1—O1—C1147.6 (2)
N3—Yb1—N1—C8167.66 (13)N3—Yb1—O1—C1136.4 (2)
N2—Yb1—N1—C858.36 (14)N2—Yb1—O1—C124.3 (2)

Experimental details

Crystal data
Chemical formula[Yb(C36H38N4O4)]ClO4·C2H3N
Mr904.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.901 (2), 13.855 (3), 21.936 (4)
β (°) 95.347 (3)
V3)3601.3 (12)
Z4
Radiation typeMo Kα
µ (mm1)2.73
Crystal size (mm)0.48 × 0.3 × 0.26
Data collection
DiffractometerSiemens SMART CCD 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.347, 0.49
No. of measured, independent and
observed [I > 2σ(I)] reflections
65102, 8961, 7644
Rint0.042
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.046, 1.09
No. of reflections8961
No. of parameters479
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.85

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Yb1—O12.1254 (15)Yb1—N12.4511 (18)
Yb1—O42.1383 (14)Yb1—N42.4560 (18)
Yb1—O32.4039 (15)Yb1—N32.6174 (18)
Yb1—O22.4184 (16)Yb1—N22.6190 (18)
O1—Yb1—O4126.76 (6)O3—Yb1—N367.97 (5)
O1—Yb1—O3150.70 (5)O3—Yb1—N267.86 (5)
O1—Yb1—O275.81 (6)O4—Yb1—O375.14 (5)
O1—Yb1—N174.01 (6)O4—Yb1—O2150.21 (5)
O1—Yb1—N478.00 (6)O4—Yb1—N175.65 (6)
O1—Yb1—N382.75 (6)O4—Yb1—N473.47 (6)
O1—Yb1—N2127.79 (6)O4—Yb1—N3129.24 (5)
O2—Yb1—N195.96 (6)O4—Yb1—N283.34 (6)
O2—Yb1—N4135.16 (5)N1—Yb1—N275.00 (6)
O2—Yb1—N366.30 (5)N1—Yb1—N3153.85 (6)
O2—Yb1—N266.86 (5)N1—Yb1—N4110.92 (6)
O3—Yb1—N1134.68 (5)N3—Yb1—N2111.91 (6)
O3—Yb1—O292.59 (5)N4—Yb1—N2153.21 (6)
O3—Yb1—N492.87 (5)N4—Yb1—N374.83 (6)
 

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