Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106023833/ob3011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106023833/ob3011Isup2.hkl |
CCDC reference: 618644
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.
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.
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).
[Yb(C36H38N4O4)]ClO4·C2H3N | F(000) = 1820 |
Mr = 904.25 | Dx = 1.668 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1499 reflections |
a = 11.901 (2) Å | θ = 2.4–28.3° |
b = 13.855 (3) Å | µ = 2.73 mm−1 |
c = 21.936 (4) Å | T = 100 K |
β = 95.347 (3)° | Prism, yellow |
V = 3601.3 (12) Å3 | 0.48 × 0.3 × 0.26 mm |
Z = 4 |
Siemens SMART CCD 1000 diffractometer | 8961 independent reflections |
Radiation source: fine-focus sealed tube | 7644 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.347, Tmax = 0.49 | k = −18→18 |
65102 measured reflections | l = −28→29 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-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 = 1.09 | Δρmax = 0.74 e Å−3 |
8961 reflections | Δρmin = −0.85 e Å−3 |
479 parameters |
[Yb(C36H38N4O4)]ClO4·C2H3N | V = 3601.3 (12) Å3 |
Mr = 904.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.901 (2) Å | µ = 2.73 mm−1 |
b = 13.855 (3) Å | T = 100 K |
c = 21.936 (4) Å | 0.48 × 0.3 × 0.26 mm |
β = 95.347 (3)° |
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 = 0.49 | Rint = 0.042 |
65102 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.74 e Å−3 |
8961 reflections | Δρmin = −0.85 e Å−3 |
479 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Yb1 | 0.185365 (7) | 0.227855 (6) | 0.423948 (4) | 0.01203 (3) | |
Cl1 | 0.45962 (5) | 0.01837 (4) | 0.17604 (2) | 0.02226 (11) | |
O1 | 0.21509 (13) | 0.21639 (10) | 0.52073 (7) | 0.0174 (3) | |
O2 | 0.38640 (13) | 0.25312 (11) | 0.44450 (7) | 0.0206 (3) | |
O3 | 0.17611 (13) | 0.32225 (10) | 0.33167 (6) | 0.0173 (3) | |
O4 | 0.04499 (12) | 0.17031 (10) | 0.36754 (7) | 0.0153 (3) | |
O5 | 0.51237 (17) | −0.07256 (14) | 0.19266 (9) | 0.0387 (5) | |
O6 | 0.50930 (17) | 0.09363 (14) | 0.21474 (9) | 0.0396 (5) | |
O7 | 0.47527 (18) | 0.04092 (15) | 0.11338 (8) | 0.0420 (5) | |
O8 | 0.34236 (15) | 0.01223 (15) | 0.18428 (10) | 0.0414 (5) | |
N1 | 0.18932 (15) | 0.05464 (13) | 0.44677 (8) | 0.0156 (4) | |
N2 | 0.30251 (15) | 0.15077 (12) | 0.34110 (8) | 0.0154 (4) | |
N3 | 0.24117 (15) | 0.40817 (12) | 0.44567 (8) | 0.0154 (4) | |
N4 | 0.01556 (15) | 0.30366 (12) | 0.45813 (8) | 0.0138 (3) | |
N5 | 0.6944 (2) | 0.2314 (2) | 0.52154 (13) | 0.0515 (7) | |
C1 | 0.26408 (18) | 0.15854 (15) | 0.56206 (10) | 0.0162 (4) | |
C2 | 0.32012 (19) | 0.19591 (17) | 0.61667 (10) | 0.0199 (5) | |
H2 | 0.3241 | 0.2623 | 0.6228 | 0.024* | |
C3 | 0.36895 (19) | 0.13442 (18) | 0.66094 (10) | 0.0217 (5) | |
H3 | 0.4087 | 0.1603 | 0.6956 | 0.026* | |
C4 | 0.3603 (2) | 0.03468 (18) | 0.65510 (11) | 0.0250 (5) | |
H4 | 0.3906 | −0.0056 | 0.6863 | 0.03* | |
C5 | 0.3064 (2) | −0.00346 (17) | 0.60241 (11) | 0.0231 (5) | |
H5 | 0.2997 | −0.0701 | 0.5983 | 0.028* | |
C6 | 0.26099 (18) | 0.05653 (15) | 0.55451 (10) | 0.0165 (4) | |
C7 | 0.21396 (18) | 0.01154 (15) | 0.49869 (10) | 0.0175 (4) | |
H7 | 0.2 | −0.0544 | 0.5 | 0.021* | |
C8 | 0.14262 (19) | −0.00465 (15) | 0.39686 (10) | 0.0163 (4) | |
C9 | 0.04046 (19) | −0.05215 (15) | 0.39962 (10) | 0.0191 (4) | |
H9 | 0.0036 | −0.0493 | 0.4351 | 0.023* | |
C10 | −0.0067 (2) | −0.10390 (16) | 0.34928 (11) | 0.0213 (5) | |
H10 | −0.0757 | −0.1349 | 0.3509 | 0.026* | |
C11 | 0.0491 (2) | −0.10933 (16) | 0.29671 (11) | 0.0214 (5) | |
H11 | 0.0182 | −0.1448 | 0.2633 | 0.026* | |
C12 | 0.15147 (19) | −0.06164 (15) | 0.29391 (10) | 0.0194 (4) | |
H12 | 0.1888 | −0.0657 | 0.2586 | 0.023* | |
C13 | 0.19836 (19) | −0.00792 (15) | 0.34357 (10) | 0.0170 (4) | |
C14 | 0.30998 (18) | 0.04256 (15) | 0.34117 (10) | 0.0178 (4) | |
H14A | 0.3603 | 0.0224 | 0.3762 | 0.021* | |
H14B | 0.3431 | 0.022 | 0.3045 | 0.021* | |
C15 | 0.42074 (18) | 0.18684 (17) | 0.34832 (10) | 0.0188 (4) | |
H15A | 0.4241 | 0.2508 | 0.3305 | 0.023* | |
H15B | 0.4687 | 0.1443 | 0.327 | 0.023* | |
C16 | 0.46220 (19) | 0.19073 (17) | 0.41514 (11) | 0.0217 (5) | |
H16A | 0.4623 | 0.1266 | 0.4329 | 0.026* | |
H16B | 0.5385 | 0.2161 | 0.4204 | 0.026* | |
C17 | 0.43637 (19) | 0.34324 (17) | 0.46477 (12) | 0.0243 (5) | |
H17A | 0.4688 | 0.375 | 0.4311 | 0.029* | |
H17B | 0.4961 | 0.332 | 0.4972 | 0.029* | |
C18 | 0.34592 (19) | 0.40589 (16) | 0.48793 (11) | 0.0205 (5) | |
H18A | 0.3282 | 0.382 | 0.5275 | 0.025* | |
H18B | 0.3746 | 0.4711 | 0.4936 | 0.025* | |
C19 | 0.2614 (2) | 0.45552 (15) | 0.38707 (10) | 0.0197 (5) | |
H19A | 0.335 | 0.437 | 0.3754 | 0.024* | |
H19B | 0.2607 | 0.5251 | 0.3921 | 0.024* | |
C20 | 0.1715 (2) | 0.42626 (15) | 0.33761 (10) | 0.0208 (5) | |
H20A | 0.0978 | 0.446 | 0.3485 | 0.025* | |
H20B | 0.185 | 0.4568 | 0.2992 | 0.025* | |
C21 | 0.2286 (2) | 0.29069 (15) | 0.27867 (10) | 0.0190 (5) | |
H21A | 0.3013 | 0.3219 | 0.2776 | 0.023* | |
H21B | 0.1817 | 0.3081 | 0.2418 | 0.023* | |
C22 | 0.24382 (19) | 0.18249 (16) | 0.28166 (9) | 0.0174 (4) | |
H22A | 0.1704 | 0.1516 | 0.2758 | 0.021* | |
H22B | 0.2872 | 0.162 | 0.2487 | 0.021* | |
C23 | 0.15747 (18) | 0.46822 (15) | 0.47492 (10) | 0.0155 (4) | |
H23A | 0.0964 | 0.4844 | 0.4442 | 0.019* | |
H23B | 0.1936 | 0.5281 | 0.4888 | 0.019* | |
C24 | 0.10815 (18) | 0.42136 (14) | 0.52833 (10) | 0.0155 (4) | |
C25 | 0.13158 (19) | 0.45613 (15) | 0.58748 (10) | 0.0191 (4) | |
H25 | 0.1838 | 0.5057 | 0.5949 | 0.023* | |
C26 | 0.0783 (2) | 0.41810 (16) | 0.63583 (10) | 0.0219 (5) | |
H26 | 0.0955 | 0.4415 | 0.6753 | 0.026* | |
C27 | −0.0005 (2) | 0.34531 (16) | 0.62493 (10) | 0.0213 (5) | |
H27 | −0.0383 | 0.3212 | 0.6569 | 0.026* | |
C28 | −0.02333 (19) | 0.30798 (15) | 0.56612 (10) | 0.0182 (4) | |
H28 | −0.075 | 0.2579 | 0.5591 | 0.022* | |
C29 | 0.03092 (18) | 0.34538 (14) | 0.51810 (9) | 0.0148 (4) | |
C30 | −0.08784 (18) | 0.29927 (14) | 0.43383 (10) | 0.0150 (4) | |
H30 | −0.1423 | 0.3282 | 0.4555 | 0.018* | |
C31 | −0.12700 (18) | 0.25405 (14) | 0.37654 (10) | 0.0150 (4) | |
C32 | −0.23891 (18) | 0.27190 (16) | 0.35214 (10) | 0.0186 (4) | |
H32 | −0.2832 | 0.3147 | 0.3722 | 0.022* | |
C33 | −0.28417 (19) | 0.22737 (17) | 0.29932 (10) | 0.0206 (4) | |
H33 | −0.3573 | 0.2411 | 0.283 | 0.025* | |
C34 | −0.21733 (19) | 0.16088 (16) | 0.27074 (10) | 0.0198 (5) | |
H34 | −0.2476 | 0.1289 | 0.2357 | 0.024* | |
C35 | −0.10798 (19) | 0.14192 (15) | 0.29340 (10) | 0.0177 (4) | |
H35 | −0.0659 | 0.0974 | 0.2734 | 0.021* | |
C36 | −0.05822 (17) | 0.18867 (15) | 0.34639 (9) | 0.0142 (4) | |
C37 | 0.6705 (2) | 0.2303 (2) | 0.57049 (13) | 0.0312 (6) | |
C38 | 0.6400 (3) | 0.2306 (2) | 0.63307 (13) | 0.0368 (6) | |
H38A | 0.7069 | 0.2242 | 0.6608 | 0.055* | |
H38B | 0.5901 | 0.1776 | 0.6388 | 0.055* | |
H38C | 0.6029 | 0.2902 | 0.641 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Yb1 | 0.01257 (4) | 0.01168 (4) | 0.01154 (4) | 0.00042 (4) | −0.00045 (3) | 0.00012 (3) |
C1 | 0.0148 (10) | 0.0206 (10) | 0.0134 (10) | 0.0027 (8) | 0.0032 (8) | 0.0024 (8) |
C2 | 0.0221 (11) | 0.0224 (11) | 0.0152 (11) | 0.0006 (9) | 0.0022 (9) | −0.0009 (8) |
C3 | 0.0180 (11) | 0.0341 (13) | 0.0128 (11) | 0.0018 (10) | 0.0005 (9) | −0.0008 (9) |
C4 | 0.0262 (13) | 0.0325 (13) | 0.0161 (11) | 0.0085 (11) | 0.0002 (9) | 0.0060 (10) |
C5 | 0.0265 (12) | 0.0212 (11) | 0.0214 (12) | 0.0045 (10) | 0.0008 (9) | 0.0033 (9) |
C6 | 0.0163 (10) | 0.0186 (10) | 0.0145 (10) | 0.0022 (8) | 0.0010 (8) | 0.0027 (8) |
C7 | 0.0180 (11) | 0.0138 (9) | 0.0208 (11) | 0.0019 (8) | 0.0024 (9) | 0.0019 (8) |
C8 | 0.0208 (11) | 0.0122 (9) | 0.0153 (10) | 0.0024 (8) | −0.0011 (8) | 0.0002 (8) |
C9 | 0.0222 (11) | 0.0155 (10) | 0.0198 (11) | −0.0003 (9) | 0.0024 (9) | 0.0009 (8) |
C10 | 0.0214 (12) | 0.0167 (10) | 0.0255 (12) | −0.0029 (9) | −0.0005 (9) | 0.0004 (9) |
C11 | 0.0262 (12) | 0.0149 (10) | 0.0216 (12) | −0.0005 (9) | −0.0047 (9) | −0.0030 (8) |
C12 | 0.0245 (12) | 0.0162 (10) | 0.0174 (11) | 0.0032 (9) | 0.0020 (9) | −0.0008 (8) |
C13 | 0.0186 (11) | 0.0142 (9) | 0.0179 (11) | 0.0036 (8) | 0.0006 (8) | −0.0001 (8) |
C14 | 0.0177 (11) | 0.0165 (10) | 0.0192 (11) | 0.0029 (9) | 0.0019 (8) | −0.0015 (8) |
C15 | 0.0129 (10) | 0.0210 (10) | 0.0228 (12) | −0.0002 (9) | 0.0038 (8) | −0.0015 (9) |
C16 | 0.0128 (10) | 0.0248 (11) | 0.0270 (12) | 0.0028 (9) | −0.0011 (9) | −0.0051 (10) |
C17 | 0.0160 (11) | 0.0225 (11) | 0.0329 (14) | −0.0025 (9) | −0.0055 (10) | −0.0044 (10) |
C18 | 0.0182 (11) | 0.0180 (10) | 0.0241 (12) | −0.0019 (9) | −0.0050 (9) | −0.0029 (9) |
C19 | 0.0237 (12) | 0.0147 (10) | 0.0213 (11) | −0.0020 (9) | 0.0053 (9) | 0.0030 (8) |
C20 | 0.0316 (13) | 0.0135 (10) | 0.0172 (11) | 0.0027 (9) | 0.0031 (9) | 0.0030 (8) |
C21 | 0.0223 (11) | 0.0210 (11) | 0.0142 (10) | 0.0034 (9) | 0.0035 (9) | 0.0010 (8) |
C22 | 0.0188 (11) | 0.0207 (10) | 0.0126 (10) | 0.0032 (9) | 0.0006 (8) | −0.0015 (8) |
C23 | 0.0173 (10) | 0.0129 (9) | 0.0159 (10) | 0.0013 (8) | −0.0001 (8) | −0.0014 (8) |
C24 | 0.0169 (10) | 0.0132 (9) | 0.0159 (10) | 0.0027 (8) | −0.0004 (8) | 0.0002 (8) |
C25 | 0.0231 (12) | 0.0143 (10) | 0.0189 (11) | 0.0003 (9) | −0.0039 (9) | −0.0025 (8) |
C26 | 0.0312 (13) | 0.0197 (11) | 0.0137 (11) | 0.0063 (10) | −0.0031 (9) | −0.0023 (8) |
C27 | 0.0309 (13) | 0.0191 (11) | 0.0144 (11) | 0.0051 (10) | 0.0045 (9) | 0.0020 (8) |
C28 | 0.0226 (11) | 0.0140 (9) | 0.0181 (11) | 0.0009 (9) | 0.0017 (9) | 0.0000 (8) |
C29 | 0.0170 (10) | 0.0130 (9) | 0.0139 (10) | 0.0033 (8) | −0.0004 (8) | −0.0019 (7) |
C30 | 0.0177 (10) | 0.0117 (9) | 0.0159 (10) | 0.0013 (8) | 0.0034 (8) | 0.0005 (7) |
C31 | 0.0153 (10) | 0.0147 (10) | 0.0151 (10) | −0.0010 (8) | 0.0016 (8) | 0.0011 (7) |
C32 | 0.0162 (10) | 0.0181 (10) | 0.0214 (11) | 0.0012 (9) | 0.0015 (8) | −0.0002 (9) |
C33 | 0.0154 (10) | 0.0230 (11) | 0.0220 (11) | 0.0006 (9) | −0.0046 (8) | 0.0011 (9) |
C34 | 0.0197 (11) | 0.0222 (11) | 0.0163 (11) | −0.0033 (9) | −0.0041 (9) | −0.0007 (8) |
C35 | 0.0194 (11) | 0.0174 (10) | 0.0160 (11) | 0.0000 (9) | 0.0007 (8) | −0.0029 (8) |
C36 | 0.0153 (10) | 0.0135 (9) | 0.0138 (10) | −0.0006 (8) | 0.0008 (8) | 0.0022 (8) |
C37 | 0.0188 (12) | 0.0362 (14) | 0.0372 (16) | 0.0060 (11) | −0.0041 (11) | −0.0033 (12) |
C38 | 0.0392 (16) | 0.0353 (14) | 0.0361 (15) | 0.0079 (13) | 0.0042 (12) | −0.0040 (12) |
Cl1 | 0.0185 (3) | 0.0308 (3) | 0.0169 (3) | 0.0073 (2) | −0.0012 (2) | −0.0020 (2) |
N1 | 0.0176 (9) | 0.0148 (8) | 0.0143 (9) | 0.0003 (7) | 0.0014 (7) | −0.0012 (7) |
N2 | 0.0144 (9) | 0.0156 (8) | 0.0161 (9) | 0.0014 (7) | 0.0011 (7) | −0.0006 (7) |
N3 | 0.0165 (9) | 0.0152 (8) | 0.0142 (9) | −0.0009 (7) | −0.0007 (7) | −0.0005 (7) |
N4 | 0.0171 (9) | 0.0112 (8) | 0.0128 (9) | −0.0012 (7) | 0.0005 (7) | −0.0012 (6) |
N5 | 0.0293 (13) | 0.086 (2) | 0.0385 (16) | 0.0126 (14) | −0.0008 (11) | 0.0013 (14) |
O1 | 0.0238 (8) | 0.0163 (7) | 0.0116 (7) | 0.0042 (6) | −0.0009 (6) | 0.0009 (6) |
O2 | 0.0139 (7) | 0.0232 (8) | 0.0243 (9) | −0.0008 (6) | 0.0002 (6) | −0.0077 (6) |
O3 | 0.0249 (8) | 0.0144 (7) | 0.0131 (7) | 0.0008 (6) | 0.0042 (6) | −0.0001 (6) |
O4 | 0.0143 (7) | 0.0149 (7) | 0.0163 (7) | 0.0024 (6) | −0.0009 (6) | −0.0021 (6) |
O5 | 0.0435 (12) | 0.0396 (11) | 0.0347 (11) | 0.0214 (9) | 0.0123 (9) | 0.0121 (9) |
O6 | 0.0445 (12) | 0.0439 (12) | 0.0287 (10) | −0.0174 (10) | −0.0052 (9) | −0.0014 (8) |
O7 | 0.0571 (13) | 0.0527 (12) | 0.0161 (9) | 0.0291 (11) | 0.0034 (9) | 0.0045 (8) |
O8 | 0.0170 (9) | 0.0567 (13) | 0.0499 (13) | 0.0033 (9) | 0.0004 (8) | −0.0185 (10) |
Yb1—O1 | 2.1254 (15) | C14—H14A | 0.97 |
Yb1—O4 | 2.1383 (14) | C14—H14B | 0.97 |
Yb1—O3 | 2.4039 (15) | C15—H15A | 0.97 |
Yb1—O2 | 2.4184 (16) | C15—H15B | 0.97 |
Yb1—N1 | 2.4511 (18) | C16—C15 | 1.503 (3) |
Yb1—N4 | 2.4560 (18) | C16—H16A | 0.97 |
Yb1—N3 | 2.6174 (18) | C16—H16B | 0.97 |
Yb1—N2 | 2.6190 (18) | C17—C18 | 1.507 (3) |
Cl1—O8 | 1.4263 (19) | C17—H17A | 0.97 |
Cl1—O6 | 1.4367 (19) | C17—H17B | 0.97 |
Cl1—O7 | 1.4386 (19) | C18—H18A | 0.97 |
Cl1—O5 | 1.4392 (19) | C18—H18B | 0.97 |
O3—C21 | 1.438 (3) | C19—H19A | 0.97 |
O3—C20 | 1.448 (2) | C19—H19B | 0.97 |
O4—C36 | 1.297 (2) | C20—C19 | 1.506 (3) |
O2—C17 | 1.436 (3) | C20—H20A | 0.97 |
O2—C16 | 1.444 (3) | C20—H20B | 0.97 |
N1—C7 | 1.295 (3) | C21—C22 | 1.511 (3) |
N1—C8 | 1.438 (3) | C21—H21A | 0.97 |
N2—C22 | 1.487 (3) | C21—H21B | 0.97 |
N2—C15 | 1.488 (3) | C22—H22A | 0.97 |
N2—C14 | 1.502 (3) | C22—H22B | 0.97 |
N3—C19 | 1.483 (3) | C23—H23A | 0.97 |
N3—C18 | 1.483 (3) | C23—H23B | 0.97 |
N3—C23 | 1.488 (3) | C24—C23 | 1.506 (3) |
N4—C30 | 1.296 (3) | C24—C25 | 1.388 (3) |
N4—C29 | 1.433 (3) | C24—C29 | 1.402 (3) |
N5—C37 | 1.136 (4) | C25—C26 | 1.389 (3) |
C1—C2 | 1.414 (3) | C25—H25 | 0.93 |
C1—O1 | 1.306 (2) | C26—H26 | 0.93 |
C2—H2 | 0.93 | C27—C26 | 1.383 (3) |
C3—C2 | 1.379 (3) | C27—H27 | 0.93 |
C3—C4 | 1.391 (3) | C28—C27 | 1.393 (3) |
C3—H3 | 0.93 | C28—H28 | 0.93 |
C4—H4 | 0.93 | C29—C28 | 1.386 (3) |
C5—C4 | 1.375 (3) | C30—H30 | 0.93 |
C5—H5 | 0.93 | C31—C30 | 1.442 (3) |
C6—C1 | 1.423 (3) | C31—C36 | 1.424 (3) |
C6—C5 | 1.407 (3) | C32—C31 | 1.410 (3) |
C6—C7 | 1.440 (3) | C32—C33 | 1.377 (3) |
C7—H7 | 0.93 | C32—H32 | 0.93 |
C8—C9 | 1.389 (3) | C33—H33 | 0.93 |
C9—H9 | 0.93 | C34—C33 | 1.403 (3) |
C10—C11 | 1.385 (3) | C34—H34 | 0.93 |
C10—C9 | 1.391 (3) | C35—C34 | 1.374 (3) |
C10—H10 | 0.93 | C35—C36 | 1.412 (3) |
C11—H11 | 0.93 | C35—H35 | 0.93 |
C12—C11 | 1.393 (3) | C37—C38 | 1.452 (4) |
C12—H12 | 0.93 | C38—H38A | 0.96 |
C13—C12 | 1.392 (3) | C38—H38B | 0.96 |
C13—C14 | 1.507 (3) | C38—H38C | 0.96 |
C13—C8 | 1.397 (3) | ||
O1—Yb1—O4 | 126.76 (6) | C36—C31—C30 | 121.86 (19) |
O1—Yb1—O3 | 150.70 (5) | O1—C1—C2 | 120.5 (2) |
O1—Yb1—O2 | 75.81 (6) | O1—C1—C6 | 121.57 (19) |
O1—Yb1—N1 | 74.01 (6) | C2—C1—C6 | 117.87 (19) |
O1—Yb1—N4 | 78.00 (6) | C29—C28—C27 | 120.0 (2) |
O1—Yb1—N3 | 82.75 (6) | C29—C28—H28 | 120 |
O1—Yb1—N2 | 127.79 (6) | C27—C28—H28 | 120 |
O2—Yb1—N1 | 95.96 (6) | C2—C3—C4 | 121.8 (2) |
O2—Yb1—N4 | 135.16 (5) | C2—C3—H3 | 119.1 |
O2—Yb1—N3 | 66.30 (5) | C4—C3—H3 | 119.1 |
O2—Yb1—N2 | 66.86 (5) | C3—C2—C1 | 120.3 (2) |
O3—Yb1—N1 | 134.68 (5) | C3—C2—H2 | 119.8 |
O3—Yb1—O2 | 92.59 (5) | C1—C2—H2 | 119.8 |
O3—Yb1—N4 | 92.87 (5) | O4—C36—C35 | 121.00 (19) |
O3—Yb1—N3 | 67.97 (5) | O4—C36—C31 | 121.64 (19) |
O3—Yb1—N2 | 67.86 (5) | C35—C36—C31 | 117.33 (19) |
O4—Yb1—O3 | 75.14 (5) | C9—C8—C13 | 120.5 (2) |
O4—Yb1—O2 | 150.21 (5) | C9—C8—N1 | 121.01 (19) |
O4—Yb1—N1 | 75.65 (6) | C13—C8—N1 | 118.38 (19) |
O4—Yb1—N4 | 73.47 (6) | O2—C17—C18 | 108.47 (18) |
O4—Yb1—N3 | 129.24 (5) | O2—C17—H17A | 110 |
O4—Yb1—N2 | 83.34 (6) | C18—C17—H17A | 110 |
N1—Yb1—N2 | 75.00 (6) | O2—C17—H17B | 110 |
N1—Yb1—N3 | 153.85 (6) | C18—C17—H17B | 110 |
N1—Yb1—N4 | 110.92 (6) | H17A—C17—H17B | 108.4 |
N3—Yb1—N2 | 111.91 (6) | C13—C12—C11 | 120.5 (2) |
N4—Yb1—N2 | 153.21 (6) | C13—C12—H12 | 119.8 |
N4—Yb1—N3 | 74.83 (6) | C11—C12—H12 | 119.8 |
O6—Cl1—O5 | 109.87 (12) | C10—C11—C12 | 120.0 (2) |
O6—Cl1—O7 | 108.91 (13) | C10—C11—H11 | 120 |
O7—Cl1—O5 | 109.87 (11) | C12—C11—H11 | 120 |
O8—Cl1—O5 | 108.94 (13) | O3—C20—C19 | 107.61 (17) |
O8—Cl1—O6 | 108.79 (12) | O3—C20—H20A | 110.2 |
O8—Cl1—O7 | 110.45 (13) | C19—C20—H20A | 110.2 |
C21—O3—C20 | 113.46 (16) | O3—C20—H20B | 110.2 |
C21—O3—Yb1 | 121.74 (12) | C19—C20—H20B | 110.2 |
C20—O3—Yb1 | 117.68 (12) | H20A—C20—H20B | 108.5 |
C36—O4—Yb1 | 142.80 (13) | N2—C14—C13 | 114.28 (17) |
C17—O2—C16 | 113.63 (17) | N2—C14—H14A | 108.7 |
C17—O2—Yb1 | 123.90 (13) | C13—C14—H14A | 108.7 |
C16—O2—Yb1 | 118.59 (12) | N2—C14—H14B | 108.7 |
C19—N3—C18 | 110.87 (17) | C13—C14—H14B | 108.7 |
C19—N3—C23 | 107.21 (16) | H14A—C14—H14B | 107.6 |
C18—N3—C23 | 107.45 (16) | N3—C19—C20 | 110.08 (18) |
C19—N3—Yb1 | 108.88 (12) | N3—C19—H19A | 109.6 |
C18—N3—Yb1 | 106.13 (12) | C20—C19—H19A | 109.6 |
C23—N3—Yb1 | 116.32 (12) | N3—C19—H19B | 109.6 |
C30—N4—C29 | 115.57 (18) | C20—C19—H19B | 109.6 |
C30—N4—Yb1 | 129.12 (14) | H19A—C19—H19B | 108.2 |
C29—N4—Yb1 | 114.49 (13) | C32—C33—C34 | 118.5 (2) |
C22—N2—C15 | 110.88 (17) | C32—C33—H33 | 120.8 |
C22—N2—C14 | 108.59 (16) | C34—C33—H33 | 120.8 |
C15—N2—C14 | 106.26 (16) | C24—C25—C26 | 121.1 (2) |
C22—N2—Yb1 | 104.53 (12) | C24—C25—H25 | 119.5 |
C15—N2—Yb1 | 110.39 (12) | C26—C25—H25 | 119.5 |
C14—N2—Yb1 | 116.21 (12) | N5—C37—C38 | 179.1 (3) |
C7—N1—C8 | 116.47 (18) | N1—C7—C6 | 125.9 (2) |
C7—N1—Yb1 | 129.01 (14) | N1—C7—H7 | 117.1 |
C8—N1—Yb1 | 113.89 (13) | C6—C7—H7 | 117.1 |
C34—C35—C36 | 121.4 (2) | N4—C30—C31 | 126.6 (2) |
C34—C35—H35 | 119.3 | N4—C30—H30 | 116.7 |
C36—C35—H35 | 119.3 | C31—C30—H30 | 116.7 |
C25—C24—C29 | 118.8 (2) | N2—C15—C16 | 109.70 (18) |
C25—C24—C23 | 121.26 (19) | N2—C15—H15A | 109.7 |
C29—C24—C23 | 119.77 (19) | C16—C15—H15A | 109.7 |
C5—C6—C1 | 119.7 (2) | N2—C15—H15B | 109.7 |
C5—C6—C7 | 118.1 (2) | C16—C15—H15B | 109.7 |
C1—C6—C7 | 122.19 (19) | H15A—C15—H15B | 108.2 |
C12—C13—C8 | 119.0 (2) | C26—C27—C28 | 120.1 (2) |
C12—C13—C14 | 120.7 (2) | C26—C27—H27 | 119.9 |
C8—C13—C14 | 120.20 (19) | C28—C27—H27 | 119.9 |
O3—C21—C22 | 109.03 (17) | C4—C5—C6 | 121.2 (2) |
O3—C21—H21A | 109.9 | C4—C5—H5 | 119.4 |
C22—C21—H21A | 109.9 | C6—C5—H5 | 119.4 |
O3—C21—H21B | 109.9 | N2—C22—C21 | 112.09 (17) |
C22—C21—H21B | 109.9 | N2—C22—H22A | 109.2 |
H21A—C21—H21B | 108.3 | C21—C22—H22A | 109.2 |
C35—C34—C33 | 121.4 (2) | N2—C22—H22B | 109.2 |
C35—C34—H34 | 119.3 | C21—C22—H22B | 109.2 |
C33—C34—H34 | 119.3 | H22A—C22—H22B | 107.9 |
C11—C10—C9 | 120.0 (2) | N3—C18—C17 | 112.75 (18) |
C11—C10—H10 | 120 | N3—C18—H18A | 109 |
C9—C10—H10 | 120 | C17—C18—H18A | 109 |
O2—C16—C15 | 107.13 (18) | N3—C18—H18B | 109 |
O2—C16—H16A | 110.3 | C17—C18—H18B | 109 |
C15—C16—H16A | 110.3 | H18A—C18—H18B | 107.8 |
O2—C16—H16B | 110.3 | C27—C26—C25 | 119.7 (2) |
C15—C16—H16B | 110.3 | C27—C26—H26 | 120.2 |
H16A—C16—H16B | 108.5 | C25—C26—H26 | 120.2 |
N3—C23—C24 | 114.81 (17) | C8—C9—C10 | 120.0 (2) |
N3—C23—H23A | 108.6 | C8—C9—H9 | 120 |
C24—C23—H23A | 108.6 | C10—C9—H9 | 120 |
N3—C23—H23B | 108.6 | C5—C4—C3 | 119.0 (2) |
C24—C23—H23B | 108.6 | C5—C4—H4 | 120.5 |
H23A—C23—H23B | 107.5 | C3—C4—H4 | 120.5 |
C28—C29—C24 | 120.26 (19) | C37—C38—H38A | 109.5 |
C28—C29—N4 | 121.22 (19) | C37—C38—H38B | 109.5 |
C24—C29—N4 | 118.40 (19) | H38A—C38—H38B | 109.5 |
C33—C32—C31 | 121.5 (2) | C37—C38—H38C | 109.5 |
C33—C32—H32 | 119.3 | H38A—C38—H38C | 109.5 |
C31—C32—H32 | 119.3 | H38B—C38—H38C | 109.5 |
C32—C31—C36 | 119.91 (19) | C1—O1—Yb1 | 139.58 (13) |
C32—C31—C30 | 118.14 (19) | ||
O1—Yb1—O3—C21 | 132.58 (16) | C20—O3—C21—C22 | 172.06 (17) |
O4—Yb1—O3—C21 | −85.00 (15) | Yb1—O3—C21—C22 | 22.3 (2) |
O2—Yb1—O3—C21 | 67.47 (15) | C36—C35—C34—C33 | −0.1 (3) |
N1—Yb1—O3—C21 | −33.54 (18) | C17—O2—C16—C15 | −110.3 (2) |
N4—Yb1—O3—C21 | −157.06 (15) | Yb1—O2—C16—C15 | 48.4 (2) |
N3—Yb1—O3—C21 | 130.57 (16) | C19—N3—C23—C24 | 167.93 (18) |
N2—Yb1—O3—C21 | 3.77 (14) | C18—N3—C23—C24 | −72.8 (2) |
O1—Yb1—O3—C20 | −16.0 (2) | Yb1—N3—C23—C24 | 45.9 (2) |
O4—Yb1—O3—C20 | 126.44 (15) | C25—C24—C23—N3 | 112.4 (2) |
O2—Yb1—O3—C20 | −81.09 (15) | C29—C24—C23—N3 | −72.1 (3) |
N1—Yb1—O3—C20 | 177.91 (13) | C25—C24—C29—C28 | 1.9 (3) |
N4—Yb1—O3—C20 | 54.38 (15) | C23—C24—C29—C28 | −173.69 (19) |
N3—Yb1—O3—C20 | −17.98 (14) | C25—C24—C29—N4 | −173.97 (19) |
N2—Yb1—O3—C20 | −144.79 (16) | C23—C24—C29—N4 | 10.4 (3) |
O1—Yb1—O4—C36 | 85.2 (2) | C30—N4—C29—C28 | 57.0 (3) |
O3—Yb1—O4—C36 | −73.0 (2) | Yb1—N4—C29—C28 | −113.64 (19) |
O2—Yb1—O4—C36 | −141.3 (2) | C30—N4—C29—C24 | −127.1 (2) |
N1—Yb1—O4—C36 | 142.1 (2) | Yb1—N4—C29—C24 | 62.2 (2) |
N4—Yb1—O4—C36 | 24.7 (2) | C33—C32—C31—C36 | 0.0 (3) |
N3—Yb1—O4—C36 | −28.8 (2) | C33—C32—C31—C30 | −176.6 (2) |
N2—Yb1—O4—C36 | −141.8 (2) | C5—C6—C1—O1 | −174.5 (2) |
O1—Yb1—O2—C17 | −80.47 (17) | C7—C6—C1—O1 | 6.3 (3) |
O4—Yb1—O2—C17 | 136.31 (16) | C5—C6—C1—C2 | 4.2 (3) |
O3—Yb1—O2—C17 | 72.28 (17) | C7—C6—C1—C2 | −175.0 (2) |
N1—Yb1—O2—C17 | −152.29 (17) | C24—C29—C28—C27 | −0.6 (3) |
N4—Yb1—O2—C17 | −24.4 (2) | N4—C29—C28—C27 | 175.2 (2) |
N3—Yb1—O2—C17 | 7.74 (16) | C4—C3—C2—C1 | −3.2 (3) |
N2—Yb1—O2—C17 | 136.84 (18) | O1—C1—C2—C3 | 178.2 (2) |
O1—Yb1—O2—C16 | 123.14 (16) | C6—C1—C2—C3 | −0.5 (3) |
O4—Yb1—O2—C16 | −20.1 (2) | Yb1—O4—C36—C35 | 158.58 (17) |
O3—Yb1—O2—C16 | −84.11 (15) | Yb1—O4—C36—C31 | −23.5 (3) |
N1—Yb1—O2—C16 | 51.33 (16) | C34—C35—C36—O4 | 179.9 (2) |
N4—Yb1—O2—C16 | 179.21 (14) | C34—C35—C36—C31 | 1.9 (3) |
N3—Yb1—O2—C16 | −148.65 (16) | C32—C31—C36—O4 | −179.85 (19) |
N2—Yb1—O2—C16 | −19.55 (14) | C30—C31—C36—O4 | −3.4 (3) |
O1—Yb1—N3—C19 | 166.97 (14) | C32—C31—C36—C35 | −1.9 (3) |
O4—Yb1—N3—C19 | −60.58 (15) | C30—C31—C36—C35 | 174.57 (19) |
O3—Yb1—N3—C19 | −14.03 (13) | C12—C13—C8—C9 | −1.7 (3) |
O2—Yb1—N3—C19 | 89.32 (14) | C14—C13—C8—C9 | −179.12 (19) |
N1—Yb1—N3—C19 | 139.76 (15) | C12—C13—C8—N1 | −177.21 (19) |
N4—Yb1—N3—C19 | −113.56 (14) | C14—C13—C8—N1 | 5.4 (3) |
N2—Yb1—N3—C19 | 39.04 (14) | C7—N1—C8—C9 | 62.1 (3) |
O1—Yb1—N3—C18 | 47.57 (13) | Yb1—N1—C8—C9 | −109.68 (19) |
O4—Yb1—N3—C18 | −179.97 (12) | C7—N1—C8—C13 | −122.4 (2) |
O3—Yb1—N3—C18 | −133.42 (14) | Yb1—N1—C8—C13 | 65.8 (2) |
O2—Yb1—N3—C18 | −30.07 (13) | C16—O2—C17—C18 | 173.70 (19) |
N1—Yb1—N3—C18 | 20.4 (2) | Yb1—O2—C17—C18 | 16.3 (3) |
N4—Yb1—N3—C18 | 127.05 (14) | C8—C13—C12—C11 | 1.7 (3) |
N2—Yb1—N3—C18 | −80.35 (14) | C14—C13—C12—C11 | 179.0 (2) |
O1—Yb1—N3—C23 | −71.85 (14) | C9—C10—C11—C12 | −1.1 (3) |
O4—Yb1—N3—C23 | 60.61 (15) | C13—C12—C11—C10 | −0.3 (3) |
O3—Yb1—N3—C23 | 107.16 (14) | C21—O3—C20—C19 | −104.0 (2) |
O2—Yb1—N3—C23 | −149.49 (15) | Yb1—O3—C20—C19 | 47.1 (2) |
N1—Yb1—N3—C23 | −99.05 (18) | C22—N2—C14—C13 | −69.2 (2) |
N4—Yb1—N3—C23 | 7.63 (13) | C15—N2—C14—C13 | 171.48 (18) |
N2—Yb1—N3—C23 | 160.23 (13) | Yb1—N2—C14—C13 | 48.2 (2) |
O1—Yb1—N4—C30 | −142.47 (18) | C12—C13—C14—N2 | 112.8 (2) |
O4—Yb1—N4—C30 | −7.94 (17) | C8—C13—C14—N2 | −69.9 (3) |
O3—Yb1—N4—C30 | 65.64 (18) | C18—N3—C19—C20 | 159.37 (18) |
O2—Yb1—N4—C30 | 162.21 (16) | C23—N3—C19—C20 | −83.6 (2) |
N1—Yb1—N4—C30 | −74.97 (18) | Yb1—N3—C19—C20 | 42.98 (19) |
N3—Yb1—N4—C30 | 131.89 (18) | O3—C20—C19—N3 | −59.4 (2) |
N2—Yb1—N4—C30 | 23.2 (2) | C31—C32—C33—C34 | 1.9 (3) |
O1—Yb1—N4—C29 | 26.62 (13) | C35—C34—C33—C32 | −1.8 (3) |
O4—Yb1—N4—C29 | 161.15 (14) | C29—C24—C25—C26 | −1.2 (3) |
O3—Yb1—N4—C29 | −125.27 (14) | C23—C24—C25—C26 | 174.3 (2) |
O2—Yb1—N4—C29 | −28.70 (17) | C8—N1—C7—C6 | −179.8 (2) |
N1—Yb1—N4—C29 | 94.11 (14) | Yb1—N1—C7—C6 | −9.5 (3) |
N3—Yb1—N4—C29 | −59.02 (13) | C5—C6—C7—N1 | −165.7 (2) |
N2—Yb1—N4—C29 | −167.72 (13) | C1—C6—C7—N1 | 13.5 (3) |
O1—Yb1—N2—C22 | −179.98 (12) | C29—N4—C30—C31 | −174.71 (19) |
O4—Yb1—N2—C22 | 47.80 (13) | Yb1—N4—C30—C31 | −5.7 (3) |
O3—Yb1—N2—C22 | −28.83 (12) | C32—C31—C30—N4 | −168.4 (2) |
O2—Yb1—N2—C22 | −131.94 (14) | C36—C31—C30—N4 | 15.1 (3) |
N1—Yb1—N2—C22 | 124.68 (13) | C22—N2—C15—C16 | 156.85 (18) |
N4—Yb1—N2—C22 | 17.9 (2) | C14—N2—C15—C16 | −85.3 (2) |
N3—Yb1—N2—C22 | −81.96 (13) | Yb1—N2—C15—C16 | 41.5 (2) |
O1—Yb1—N2—C15 | −60.70 (15) | O2—C16—C15—N2 | −58.2 (2) |
O4—Yb1—N2—C15 | 167.08 (14) | C29—C28—C27—C26 | −1.6 (3) |
O3—Yb1—N2—C15 | 90.45 (14) | C1—C6—C5—C4 | −4.2 (3) |
O2—Yb1—N2—C15 | −12.66 (12) | C7—C6—C5—C4 | 174.9 (2) |
N1—Yb1—N2—C15 | −116.04 (14) | C15—N2—C22—C21 | −65.8 (2) |
N4—Yb1—N2—C15 | 137.15 (14) | C14—N2—C22—C21 | 177.76 (17) |
N3—Yb1—N2—C15 | 37.33 (14) | Yb1—N2—C22—C21 | 53.11 (19) |
O1—Yb1—N2—C14 | 60.36 (16) | O3—C21—C22—N2 | −52.1 (2) |
O4—Yb1—N2—C14 | −71.86 (14) | C19—N3—C18—C17 | −65.7 (2) |
O3—Yb1—N2—C14 | −148.48 (15) | C23—N3—C18—C17 | 177.41 (18) |
O2—Yb1—N2—C14 | 108.40 (14) | Yb1—N3—C18—C17 | 52.3 (2) |
N1—Yb1—N2—C14 | 5.02 (13) | O2—C17—C18—N3 | −46.9 (3) |
N4—Yb1—N2—C14 | −101.79 (17) | C28—C27—C26—C25 | 2.3 (3) |
N3—Yb1—N2—C14 | 158.39 (13) | C24—C25—C26—C27 | −0.9 (3) |
O1—Yb1—N1—C7 | −6.33 (18) | C13—C8—C9—C10 | 0.4 (3) |
O4—Yb1—N1—C7 | −142.05 (19) | N1—C8—C9—C10 | 175.8 (2) |
O3—Yb1—N1—C7 | 166.65 (16) | C11—C10—C9—C8 | 1.0 (3) |
O2—Yb1—N1—C7 | 67.04 (19) | C6—C5—C4—C3 | 0.6 (4) |
N4—Yb1—N1—C7 | −76.39 (19) | C2—C3—C4—C5 | 3.2 (4) |
N3—Yb1—N1—C7 | 21.8 (3) | C2—C1—O1—Yb1 | 144.29 (18) |
N2—Yb1—N1—C7 | 131.12 (19) | C6—C1—O1—Yb1 | −37.1 (3) |
O1—Yb1—N1—C8 | 164.19 (15) | O4—Yb1—O1—C1 | 89.1 (2) |
O4—Yb1—N1—C8 | 28.47 (14) | O3—Yb1—O1—C1 | −138.3 (2) |
O3—Yb1—N1—C8 | −22.83 (17) | O2—Yb1—O1—C1 | −69.1 (2) |
O2—Yb1—N1—C8 | −122.44 (14) | N1—Yb1—O1—C1 | 31.5 (2) |
N4—Yb1—N1—C8 | 94.13 (14) | N4—Yb1—O1—C1 | 147.6 (2) |
N3—Yb1—N1—C8 | −167.66 (13) | N3—Yb1—O1—C1 | −136.4 (2) |
N2—Yb1—N1—C8 | −58.36 (14) | N2—Yb1—O1—C1 | −24.3 (2) |
Experimental details
Crystal data | |
Chemical formula | [Yb(C36H38N4O4)]ClO4·C2H3N |
Mr | 904.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.901 (2), 13.855 (3), 21.936 (4) |
β (°) | 95.347 (3) |
V (Å3) | 3601.3 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.73 |
Crystal size (mm) | 0.48 × 0.3 × 0.26 |
Data collection | |
Diffractometer | Siemens SMART CCD 1000 diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.347, 0.49 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 65102, 8961, 7644 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.020, 0.046, 1.09 |
No. of reflections | 8961 |
No. of parameters | 479 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
Yb1—O1 | 2.1254 (15) | Yb1—N1 | 2.4511 (18) |
Yb1—O4 | 2.1383 (14) | Yb1—N4 | 2.4560 (18) |
Yb1—O3 | 2.4039 (15) | Yb1—N3 | 2.6174 (18) |
Yb1—O2 | 2.4184 (16) | Yb1—N2 | 2.6190 (18) |
O1—Yb1—O4 | 126.76 (6) | O3—Yb1—N3 | 67.97 (5) |
O1—Yb1—O3 | 150.70 (5) | O3—Yb1—N2 | 67.86 (5) |
O1—Yb1—O2 | 75.81 (6) | O4—Yb1—O3 | 75.14 (5) |
O1—Yb1—N1 | 74.01 (6) | O4—Yb1—O2 | 150.21 (5) |
O1—Yb1—N4 | 78.00 (6) | O4—Yb1—N1 | 75.65 (6) |
O1—Yb1—N3 | 82.75 (6) | O4—Yb1—N4 | 73.47 (6) |
O1—Yb1—N2 | 127.79 (6) | O4—Yb1—N3 | 129.24 (5) |
O2—Yb1—N1 | 95.96 (6) | O4—Yb1—N2 | 83.34 (6) |
O2—Yb1—N4 | 135.16 (5) | N1—Yb1—N2 | 75.00 (6) |
O2—Yb1—N3 | 66.30 (5) | N1—Yb1—N3 | 153.85 (6) |
O2—Yb1—N2 | 66.86 (5) | N1—Yb1—N4 | 110.92 (6) |
O3—Yb1—N1 | 134.68 (5) | N3—Yb1—N2 | 111.91 (6) |
O3—Yb1—O2 | 92.59 (5) | N4—Yb1—N2 | 153.21 (6) |
O3—Yb1—N4 | 92.87 (5) | N4—Yb1—N3 | 74.83 (6) |
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.