Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702795X/bi2193sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702795X/bi2193Isup2.hkl |
CCDC reference: 654766
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.008 Å
- Disorder in solvent or counterion
- R factor = 0.051
- wR factor = 0.115
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 15.00 Perc.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C18 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C44 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a general discussion of macrocyclic lanthanide complexes, see Bunzli & Piguet (2002). Some examples of symmetric macrocyclic lanthanide complexes are given in Hu et al. (2005). The GdIII and LuIII analogues of the title complex have been reported recently (Hu, Qiu et al., 2007; Hu, Chen et al., 2007).
To a methanolic solution (20 ml) of 2,6-diformyl-4-methylphenol (1 mmol) and Dy(NO3)3.6H2O (0.5 mmol), 1,5-diamino-3-azapentane (1 mmol) was added dropwise. After refluxing for 3 h, the solvent was removed. The resulting yellow solid was recrystallized from CH3CN, yielding yellow block crystals suitable for X-ray analysis.
H atoms bound to C atoms were placed geometrically (C—H 0.93 to 0.97 Å) and were allowed to ride during refinement with Uiso(H) = 1.2Ueq(C). H atoms bound to N atoms were visible in difference Fourier maps, but were placed geometrically with N—H = 0.90 or 0.91 Å for N(sp3) and 0.86 Å for N(sp2), and allowed to ride during refinement with Uiso(H) = 1.2Ueq(N). H atoms of the water molecules were located in difference Fourier maps, then their O—H distances were normalized to 0.85 Å and they were refined as riding with Uiso(H) = 1.2Ueq(O).
Lanthanide macrocyclic complexes have received much attention due to their unique properties and many valuable applications such as fluorescent probes in biological systems, material science and chemical processes (Bunzli & Piguet, 2002). Generally, the syntheses of lanthanide macrocyclic complexes are carried out in the presence of a suitable lanthanide ion which acts as a template for macrocycle formation, Most of them are symmetric (Hu et al., 2005). There have been few reports of asymmetric lanthanide complexes.
Recently, Hu et al. (Hu, Qiu et al., 2007; Hu, Chen et al., 2007) have reported the crystal structures of GdIII and LuIII complexes with a macrocyclic ligand derived from 2,6-diformyl-4-methylphenol and 1,5-diamino-3-azapentane: [Gd(C26H34N6O2)(NO3)2]+(NO3)-.H2O and [Lu(C26H34N6O2)(NO3)2]+(NO3)-.0.5H2O.0.25CH3COOC2H5. In these complexes, the central lanthanide ion is nine-coordinate, being bound to five donor atoms from the cyclic polydentate ligand and to four O of two bidentate nitrate anions. Reported here is a new DyIII analogue [Dy(III)(C26H34N6O2)(NO3)2]+(NO3)-.H2O, which exhibits a similar nine-coordinate distorted tricapped trigonal prismatic coordination geometry (Fig. 1 & Fig. 2). The title complex is not isostructural with its GdIII and LuIII analogues. (space groups Cc and C2/c, respectively).
For a general discussion of macrocyclic lanthanide complexes, see Bunzli & Piguet (2002). Some examples of symmetric macrocyclic lanthanide complexes are given in Hu et al. (2005). The GdIII and LuIII analogues of the title complex have been reported recently (Hu, Qiu et al., 2007; Hu, Chen et al., 2007).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Dy(C26H34N6O2)(NO3)2]NO3·H2O | Z = 4 |
Mr = 829.14 | F(000) = 1668 |
Triclinic, P1 | Dx = 1.504 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.005 (3) Å | Cell parameters from 6195 reflections |
b = 14.045 (3) Å | θ = 2.5–22.7° |
c = 21.896 (4) Å | µ = 2.11 mm−1 |
α = 96.386 (3)° | T = 292 K |
β = 99.094 (3)° | Block, yellow |
γ = 118.217 (3)° | 0.30 × 0.22 × 0.20 mm |
V = 3661.0 (13) Å3 |
Bruker SMART CCD diffractometer | 14395 independent reflections |
Radiation source: sealed tube | 10889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 26.0°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −17→17 |
Tmin = 0.58, Tmax = 0.66 | k = −17→17 |
36705 measured reflections | l = −27→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full with fixed elements per cycle | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
14395 reflections | (Δ/σ)max < 0.001 |
872 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −1.42 e Å−3 |
[Dy(C26H34N6O2)(NO3)2]NO3·H2O | γ = 118.217 (3)° |
Mr = 829.14 | V = 3661.0 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 14.005 (3) Å | Mo Kα radiation |
b = 14.045 (3) Å | µ = 2.11 mm−1 |
c = 21.896 (4) Å | T = 292 K |
α = 96.386 (3)° | 0.30 × 0.22 × 0.20 mm |
β = 99.094 (3)° |
Bruker SMART CCD diffractometer | 14395 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 10889 reflections with I > 2σ(I) |
Tmin = 0.58, Tmax = 0.66 | Rint = 0.042 |
36705 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.45 e Å−3 |
14395 reflections | Δρmin = −1.42 e Å−3 |
872 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.47785 (19) | 0.8435 (3) | 0.33060 (16) | 0.0424 (11) | |
C2 | 0.3861 (3) | 0.7491 (2) | 0.33767 (16) | 0.0457 (11) | |
C3 | 0.2811 (2) | 0.7395 (2) | 0.32526 (17) | 0.0501 (12) | |
H3 | 0.2197 | 0.6763 | 0.3300 | 0.060* | |
C4 | 0.2679 (2) | 0.8243 (3) | 0.30578 (16) | 0.0487 (12) | |
C5 | 0.3597 (3) | 0.9188 (2) | 0.29872 (17) | 0.0518 (12) | |
H5 | 0.3509 | 0.9755 | 0.2857 | 0.062* | |
C6 | 0.4647 (2) | 0.9284 (2) | 0.31113 (17) | 0.0626 (15) | |
C7 | 0.3928 (4) | 0.6602 (4) | 0.3563 (2) | 0.0423 (11) | |
H7 | 0.3267 | 0.5988 | 0.3580 | 0.051* | |
C8 | 0.1511 (5) | 0.8098 (5) | 0.2895 (3) | 0.0620 (15) | |
H8A | 0.1469 | 0.8625 | 0.3192 | 0.093* | |
H8B | 0.0972 | 0.7363 | 0.2915 | 0.093* | |
H8C | 0.1357 | 0.8214 | 0.2475 | 0.093* | |
C9 | 0.5574 (5) | 1.0360 (5) | 0.3046 (3) | 0.0622 (14) | |
H9 | 0.5392 | 1.0901 | 0.2970 | 0.075* | |
C10 | 0.8457 (3) | 0.7694 (3) | 0.34372 (15) | 0.0533 (13) | |
C11 | 0.9485 (3) | 0.83720 (19) | 0.38639 (15) | 0.0465 (11) | |
C12 | 1.0079 (2) | 0.7912 (2) | 0.41481 (14) | 0.0528 (13) | |
H12 | 1.0767 | 0.8365 | 0.4434 | 0.063* | |
C13 | 0.9645 (3) | 0.6774 (2) | 0.40058 (15) | 0.0461 (11) | |
C14 | 0.8618 (3) | 0.60959 (19) | 0.35791 (16) | 0.0528 (13) | |
H14 | 0.8327 | 0.5334 | 0.3484 | 0.063* | |
C15 | 0.8024 (2) | 0.6556 (2) | 0.32948 (14) | 0.0560 (13) | |
C16 | 1.0050 (5) | 0.9589 (5) | 0.4031 (2) | 0.0616 (15) | |
H16 | 1.0794 | 0.9956 | 0.4254 | 0.074* | |
C17 | 1.0299 (4) | 0.6233 (5) | 0.4289 (2) | 0.0531 (13) | |
H17A | 1.0693 | 0.6117 | 0.3994 | 0.080* | |
H17B | 0.9788 | 0.5536 | 0.4371 | 0.080* | |
H17C | 1.0823 | 0.6711 | 0.4677 | 0.080* | |
C18 | 0.6876 (5) | 0.5791 (5) | 0.2826 (2) | 0.0580 (14) | |
H18 | 0.6739 | 0.5032 | 0.2730 | 0.070* | |
C19 | 0.4863 (4) | 0.5560 (4) | 0.3875 (3) | 0.0500 (12) | |
H19A | 0.4148 | 0.4912 | 0.3668 | 0.060* | |
H19B | 0.4963 | 0.5611 | 0.4328 | 0.060* | |
C20 | 0.5788 (5) | 0.5432 (5) | 0.3666 (3) | 0.0619 (15) | |
H20A | 0.6477 | 0.5863 | 0.3992 | 0.074* | |
H20B | 0.5595 | 0.4662 | 0.3604 | 0.074* | |
C21 | 0.4973 (4) | 0.5106 (5) | 0.2517 (3) | 0.0616 (16) | |
H21A | 0.4337 | 0.5200 | 0.2547 | 0.074* | |
H21B | 0.4751 | 0.4330 | 0.2476 | 0.074* | |
C22 | 0.5480 (4) | 0.5575 (4) | 0.1967 (2) | 0.0515 (13) | |
H22A | 0.5254 | 0.6091 | 0.1837 | 0.062* | |
H22B | 0.5255 | 0.4986 | 0.1605 | 0.062* | |
C23 | 1.0414 (4) | 1.1413 (5) | 0.4118 (3) | 0.0549 (14) | |
H23A | 1.0911 | 1.1567 | 0.4524 | 0.066* | |
H23B | 1.0865 | 1.1675 | 0.3816 | 0.066* | |
C24 | 0.9790 (4) | 1.1999 (4) | 0.4176 (2) | 0.0549 (14) | |
H24A | 1.0294 | 1.2791 | 0.4253 | 0.066* | |
H24B | 0.9446 | 1.1842 | 0.4531 | 0.066* | |
C25 | 0.8306 (4) | 1.2242 (5) | 0.3592 (2) | 0.0531 (13) | |
H25A | 0.8800 | 1.3012 | 0.3592 | 0.064* | |
H25B | 0.8029 | 1.2212 | 0.3973 | 0.064* | |
C26 | 0.7338 (5) | 1.1730 (5) | 0.3014 (3) | 0.0654 (15) | |
H26A | 0.6969 | 1.2165 | 0.2990 | 0.078* | |
H26B | 0.7599 | 1.1696 | 0.2632 | 0.078* | |
C27 | 0.2983 (4) | −0.1020 (4) | 0.1215 (2) | 0.0450 (11) | |
C28 | 0.3961 (4) | −0.1080 (5) | 0.1358 (2) | 0.0473 (12) | |
C29 | 0.3941 (4) | −0.2033 (4) | 0.1516 (2) | 0.0446 (11) | |
H29 | 0.4603 | −0.2049 | 0.1612 | 0.054* | |
C30 | 0.2948 (4) | −0.2947 (4) | 0.1532 (2) | 0.0450 (11) | |
C31 | 0.1949 (5) | −0.2905 (5) | 0.1391 (3) | 0.0565 (13) | |
H31 | 0.1278 | −0.3508 | 0.1405 | 0.068* | |
C32 | 0.1965 (5) | −0.1951 (4) | 0.1228 (3) | 0.0531 (12) | |
C33 | 0.5050 (4) | −0.0196 (5) | 0.1327 (2) | 0.0498 (12) | |
H33 | 0.5624 | −0.0360 | 0.1379 | 0.060* | |
C34 | 0.2921 (5) | −0.3957 (5) | 0.1720 (3) | 0.0557 (13) | |
H34A | 0.2948 | −0.4404 | 0.1366 | 0.084* | |
H34B | 0.2246 | −0.4377 | 0.1852 | 0.084* | |
H34C | 0.3553 | −0.3734 | 0.2064 | 0.084* | |
C35 | 0.0938 (4) | −0.2017 (4) | 0.1077 (2) | 0.0420 (11) | |
H35 | 0.0314 | −0.2654 | 0.1109 | 0.050* | |
C36 | 0.2392 (4) | 0.2650 (4) | 0.1082 (3) | 0.0543 (13) | |
C37 | 0.2605 (4) | 0.3269 (4) | 0.0600 (2) | 0.0492 (12) | |
C38 | 0.1853 (4) | 0.3658 (4) | 0.0384 (3) | 0.0514 (13) | |
H38 | 0.1995 | 0.4079 | 0.0076 | 0.062* | |
C39 | 0.0952 (5) | 0.3430 (4) | 0.0615 (3) | 0.0572 (15) | |
C40 | 0.0692 (5) | 0.2750 (4) | 0.1055 (2) | 0.0539 (13) | |
H40 | 0.0034 | 0.2540 | 0.1187 | 0.065* | |
C41 | 0.1393 (4) | 0.2397 (4) | 0.1287 (2) | 0.0433 (11) | |
C42 | 0.3492 (4) | 0.3483 (4) | 0.0306 (2) | 0.0421 (10) | |
H42A | 0.3568 | 0.3914 | 0.0004 | 0.050* | |
C43 | 0.0218 (4) | 0.3921 (4) | 0.0331 (2) | 0.0550 (14) | |
H43A | 0.0479 | 0.4641 | 0.0582 | 0.083* | |
H43B | −0.0547 | 0.3442 | 0.0333 | 0.083* | |
H43C | 0.0274 | 0.3979 | −0.0097 | 0.083* | |
C44 | 0.1037 (5) | 0.1637 (4) | 0.1756 (3) | 0.0586 (14) | |
H44 | 0.0403 | 0.1628 | 0.1897 | 0.070* | |
C45 | 0.1679 (4) | 0.0949 (5) | 0.2612 (2) | 0.0517 (12) | |
H45A | 0.2276 | 0.0775 | 0.2676 | 0.062* | |
H45B | 0.1478 | 0.1033 | 0.3011 | 0.062* | |
C46 | 0.0712 (4) | 0.0098 (5) | 0.2122 (2) | 0.0463 (11) | |
H46A | 0.0727 | −0.0589 | 0.2058 | 0.056* | |
H46B | 0.0021 | −0.0040 | 0.2232 | 0.056* | |
C47 | −0.0090 (4) | −0.0068 (4) | 0.1010 (3) | 0.0521 (13) | |
H47A | 0.0066 | 0.0308 | 0.0662 | 0.062* | |
H47B | −0.0762 | −0.0110 | 0.1103 | 0.062* | |
C48 | −0.0293 (4) | −0.1248 (4) | 0.0808 (2) | 0.0458 (11) | |
H48A | −0.0734 | −0.1719 | 0.1065 | 0.055* | |
H48B | −0.0705 | −0.1552 | 0.0369 | 0.055* | |
C49 | 0.6479 (4) | 0.1487 (4) | 0.1208 (2) | 0.0435 (11) | |
H49A | 0.6855 | 0.1059 | 0.1196 | 0.052* | |
H49B | 0.6874 | 0.2086 | 0.1580 | 0.052* | |
C50 | 0.6474 (4) | 0.1958 (4) | 0.0607 (2) | 0.0470 (11) | |
H50A | 0.7235 | 0.2443 | 0.0584 | 0.056* | |
H50B | 0.6116 | 0.1358 | 0.0236 | 0.056* | |
C51 | 0.5600 (4) | 0.2838 (5) | −0.0015 (2) | 0.0520 (13) | |
H51A | 0.5052 | 0.2163 | −0.0318 | 0.062* | |
H51B | 0.6265 | 0.3184 | −0.0175 | 0.062* | |
C52 | 0.5134 (4) | 0.3620 (4) | 0.0067 (2) | 0.0483 (12) | |
H52A | 0.5722 | 0.4342 | 0.0310 | 0.058* | |
H52B | 0.4850 | 0.3707 | −0.0344 | 0.058* | |
Dy1 | 0.75925 (2) | 0.95316 (2) | 0.336610 (11) | 0.05113 (8) | |
Dy2 | 0.407500 (18) | 0.16379 (2) | 0.100570 (12) | 0.04739 (8) | |
N1 | 0.4865 (4) | 0.6566 (4) | 0.3717 (2) | 0.0529 (11) | |
H1A | 0.5490 | 0.7138 | 0.3725 | 0.063* | |
N2 | 0.6562 (4) | 1.0606 (4) | 0.3082 (2) | 0.0573 (12) | |
N3 | 0.8918 (4) | 1.1639 (3) | 0.3585 (2) | 0.0463 (10) | |
H3A | 0.9267 | 1.1785 | 0.3262 | 0.056* | |
N4 | 0.9631 (4) | 1.0184 (4) | 0.3904 (2) | 0.0538 (11) | |
N5 | 0.6776 (4) | 0.6179 (4) | 0.2258 (2) | 0.0601 (12) | |
H5A | 0.7121 | 0.5997 | 0.1992 | 0.072* | |
H5B | 0.7072 | 0.6918 | 0.2342 | 0.072* | |
N6 | 0.5944 (3) | 0.5815 (4) | 0.3070 (2) | 0.0537 (11) | |
N7 | 0.7380 (4) | 0.9146 (4) | 0.1990 (2) | 0.0596 (12) | |
N8 | 0.7392 (4) | 0.9437 (4) | 0.4685 (2) | 0.0592 (13) | |
N9 | 0.5318 (4) | 0.0781 (4) | 0.1236 (2) | 0.0586 (12) | |
N10 | 0.0796 (3) | −0.1221 (4) | 0.0888 (2) | 0.0480 (10) | |
H10A | 0.1353 | −0.0669 | 0.0810 | 0.058* | |
N11 | 0.0828 (3) | 0.0565 (3) | 0.15591 (19) | 0.0438 (9) | |
N12 | 0.2046 (4) | 0.2077 (4) | 0.2318 (2) | 0.0575 (12) | |
H12A | 0.2115 | 0.2641 | 0.2597 | 0.069* | |
H12B | 0.2686 | 0.2291 | 0.2192 | 0.069* | |
N13 | 0.4212 (4) | 0.3152 (4) | 0.0404 (2) | 0.0567 (12) | |
N14 | 0.5880 (3) | 0.2569 (3) | 0.06133 (18) | 0.0430 (9) | |
H14A | 0.6345 | 0.3227 | 0.0891 | 0.052* | |
N15 | 0.5202 (4) | 0.2597 (3) | 0.2372 (2) | 0.0504 (11) | |
N16 | 0.2567 (3) | 0.0129 (3) | −0.01617 (18) | 0.0423 (9) | |
N17 | 0.1430 (4) | 0.3787 (3) | 0.3121 (2) | 0.0550 (12) | |
N18 | 0.8148 (4) | 0.5559 (4) | 0.1309 (2) | 0.0554 (11) | |
O1 | 0.5778 (3) | 0.8473 (3) | 0.33876 (17) | 0.0556 (9) | |
O2 | 0.7896 (3) | 0.8106 (3) | 0.31100 (18) | 0.0645 (11) | |
O3 | 0.6560 (3) | 0.8534 (3) | 0.22214 (19) | 0.0638 (11) | |
O4 | 0.8157 (3) | 0.9962 (3) | 0.23469 (16) | 0.0511 (9) | |
O5 | 0.7318 (3) | 0.8909 (3) | 0.14592 (18) | 0.0582 (10) | |
O6 | 0.7480 (3) | 0.8677 (3) | 0.43658 (16) | 0.0534 (9) | |
O7 | 0.7562 (3) | 1.0260 (3) | 0.44466 (17) | 0.0566 (10) | |
O8 | 0.7203 (3) | 0.9337 (3) | 0.52032 (18) | 0.0593 (10) | |
O9 | 0.2978 (3) | −0.0141 (3) | 0.10996 (16) | 0.0466 (8) | |
O10 | 0.3063 (3) | 0.2363 (3) | 0.13515 (16) | 0.0457 (8) | |
O11 | 0.4298 (3) | 0.1682 (3) | 0.21994 (16) | 0.0539 (9) | |
O12 | 0.5602 (3) | 0.3048 (3) | 0.19477 (16) | 0.0469 (8) | |
O13 | 0.5665 (3) | 0.3021 (3) | 0.29462 (19) | 0.0620 (10) | |
O14 | 0.3596 (2) | 0.0465 (3) | −0.00753 (15) | 0.0410 (7) | |
O15 | 0.2248 (3) | 0.0671 (3) | 0.01518 (15) | 0.0483 (8) | |
O16 | 0.1887 (3) | −0.0741 (3) | −0.05426 (17) | 0.0627 (11) | |
O17 | 0.0664 (3) | 0.2836 (3) | 0.28828 (18) | 0.0665 (12) | |
O18 | 0.2305 (3) | 0.4028 (3) | 0.29827 (19) | 0.0637 (11) | |
O19 | 0.1357 (3) | 0.4538 (3) | 0.34430 (18) | 0.0616 (10) | |
O20 | 0.7317 (3) | 0.5001 (3) | 0.13864 (19) | 0.0686 (12) | |
O21 | 0.8556 (4) | 0.6503 (4) | 0.15550 (19) | 0.0661 (11) | |
O22 | 0.8672 (3) | 0.5325 (4) | 0.09746 (18) | 0.0649 (11) | |
O23 | 0.9291 (9) | 0.4352 (9) | 0.2281 (5) | 0.071 (3) | 0.40 |
H23D | 0.9409 | 0.4081 | 0.2593 | 0.085* | 0.40 |
H23E | 0.8911 | 0.3836 | 0.1953 | 0.085* | 0.40 |
O24 | 0.2786 (8) | 0.5461 (8) | 0.5132 (4) | 0.058 (2) | 0.40 |
H24C | 0.2583 | 0.4991 | 0.5366 | 0.069* | 0.40 |
H24E | 0.2217 | 0.5358 | 0.4866 | 0.069* | 0.40 |
O25 | 0.6348 (8) | 0.7333 (8) | 0.5865 (4) | 0.065 (3) | 0.40 |
H25D | 0.6597 | 0.6894 | 0.5920 | 0.078* | 0.40 |
H25E | 0.6646 | 0.7713 | 0.5603 | 0.078* | 0.40 |
O26 | 0.4610 (10) | 0.8251 (10) | 0.5315 (6) | 0.087 (4) | 0.40 |
H26E | 0.5163 | 0.8174 | 0.5460 | 0.105* | 0.40 |
H26D | 0.4735 | 0.8536 | 0.4993 | 0.105* | 0.40 |
O27 | 0.3462 (10) | 0.6915 (12) | 0.5223 (5) | 0.097 (5) | 0.40 |
H27C | 0.3388 | 0.6655 | 0.5556 | 0.117* | 0.40 |
H27A | 0.2893 | 0.6967 | 0.5076 | 0.117* | 0.40 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.039 (2) | 0.056 (3) | 0.043 (2) | 0.033 (2) | 0.0094 (19) | 0.007 (2) |
C2 | 0.036 (2) | 0.037 (3) | 0.072 (3) | 0.024 (2) | 0.012 (2) | 0.013 (2) |
C3 | 0.041 (3) | 0.052 (3) | 0.050 (3) | 0.017 (2) | 0.016 (2) | 0.008 (2) |
C4 | 0.040 (3) | 0.047 (3) | 0.061 (3) | 0.021 (2) | 0.016 (2) | 0.016 (2) |
C5 | 0.051 (3) | 0.054 (3) | 0.052 (3) | 0.027 (3) | 0.014 (2) | 0.008 (2) |
C6 | 0.060 (3) | 0.065 (4) | 0.048 (3) | 0.019 (3) | 0.018 (3) | 0.009 (3) |
C7 | 0.040 (2) | 0.032 (2) | 0.038 (2) | 0.009 (2) | 0.0065 (18) | −0.0072 (18) |
C8 | 0.064 (4) | 0.055 (3) | 0.058 (3) | 0.021 (3) | 0.019 (3) | 0.012 (3) |
C9 | 0.051 (3) | 0.051 (3) | 0.076 (4) | 0.019 (3) | 0.014 (3) | 0.014 (3) |
C10 | 0.050 (3) | 0.062 (3) | 0.031 (2) | 0.016 (3) | 0.009 (2) | 0.004 (2) |
C11 | 0.040 (3) | 0.039 (3) | 0.052 (3) | 0.012 (2) | 0.013 (2) | 0.013 (2) |
C12 | 0.056 (3) | 0.037 (3) | 0.041 (2) | 0.007 (2) | 0.005 (2) | 0.008 (2) |
C13 | 0.041 (3) | 0.054 (3) | 0.044 (2) | 0.021 (2) | 0.016 (2) | 0.019 (2) |
C14 | 0.053 (3) | 0.031 (3) | 0.061 (3) | 0.009 (2) | 0.017 (2) | 0.009 (2) |
C15 | 0.056 (3) | 0.047 (3) | 0.053 (3) | 0.017 (3) | 0.013 (2) | 0.006 (2) |
C16 | 0.056 (3) | 0.059 (4) | 0.045 (3) | 0.013 (3) | 0.006 (2) | 0.002 (2) |
C17 | 0.044 (3) | 0.051 (3) | 0.047 (3) | 0.012 (2) | 0.006 (2) | 0.010 (2) |
C18 | 0.051 (3) | 0.059 (3) | 0.044 (3) | 0.021 (3) | 0.000 (2) | −0.016 (2) |
C19 | 0.041 (3) | 0.046 (3) | 0.055 (3) | 0.015 (2) | 0.009 (2) | 0.015 (2) |
C20 | 0.042 (3) | 0.059 (4) | 0.066 (3) | 0.010 (3) | 0.019 (3) | 0.006 (3) |
C21 | 0.038 (3) | 0.062 (4) | 0.056 (3) | 0.019 (3) | −0.016 (2) | −0.025 (3) |
C22 | 0.043 (3) | 0.040 (3) | 0.047 (3) | 0.013 (2) | −0.013 (2) | −0.012 (2) |
C23 | 0.030 (2) | 0.066 (4) | 0.051 (3) | 0.010 (2) | 0.013 (2) | 0.007 (3) |
C24 | 0.048 (3) | 0.033 (3) | 0.055 (3) | 0.000 (2) | 0.006 (2) | 0.006 (2) |
C25 | 0.045 (3) | 0.049 (3) | 0.050 (3) | 0.010 (2) | 0.010 (2) | 0.022 (2) |
C26 | 0.061 (4) | 0.065 (4) | 0.067 (4) | 0.029 (3) | 0.014 (3) | 0.017 (3) |
C27 | 0.048 (3) | 0.045 (3) | 0.033 (2) | 0.019 (2) | 0.0073 (19) | −0.0041 (19) |
C28 | 0.045 (3) | 0.053 (3) | 0.039 (2) | 0.027 (2) | −0.004 (2) | −0.001 (2) |
C29 | 0.037 (2) | 0.046 (3) | 0.045 (2) | 0.022 (2) | 0.0017 (19) | −0.007 (2) |
C30 | 0.052 (3) | 0.039 (3) | 0.045 (2) | 0.030 (2) | −0.002 (2) | −0.001 (2) |
C31 | 0.057 (3) | 0.042 (3) | 0.065 (3) | 0.020 (3) | 0.010 (3) | 0.022 (3) |
C32 | 0.049 (3) | 0.041 (3) | 0.057 (3) | 0.017 (2) | 0.006 (2) | 0.003 (2) |
C33 | 0.029 (2) | 0.062 (3) | 0.045 (3) | 0.019 (2) | −0.0042 (19) | −0.005 (2) |
C34 | 0.047 (3) | 0.067 (4) | 0.054 (3) | 0.029 (3) | 0.011 (2) | 0.015 (3) |
C35 | 0.030 (2) | 0.021 (2) | 0.060 (3) | 0.0082 (18) | 0.0037 (19) | −0.0158 (19) |
C36 | 0.041 (3) | 0.039 (3) | 0.062 (3) | 0.008 (2) | 0.008 (2) | −0.001 (2) |
C37 | 0.042 (3) | 0.040 (3) | 0.052 (3) | 0.016 (2) | 0.000 (2) | −0.005 (2) |
C38 | 0.043 (3) | 0.032 (3) | 0.058 (3) | 0.014 (2) | −0.012 (2) | −0.012 (2) |
C39 | 0.060 (3) | 0.033 (3) | 0.060 (3) | 0.025 (3) | −0.018 (3) | −0.021 (2) |
C40 | 0.059 (3) | 0.036 (3) | 0.044 (3) | 0.018 (2) | −0.009 (2) | −0.019 (2) |
C41 | 0.039 (2) | 0.040 (3) | 0.049 (3) | 0.022 (2) | 0.005 (2) | −0.006 (2) |
C42 | 0.043 (3) | 0.034 (2) | 0.055 (3) | 0.023 (2) | 0.012 (2) | 0.009 (2) |
C43 | 0.046 (3) | 0.042 (3) | 0.050 (3) | 0.014 (2) | −0.021 (2) | −0.010 (2) |
C44 | 0.055 (3) | 0.035 (3) | 0.071 (4) | 0.011 (2) | 0.008 (3) | 0.020 (3) |
C45 | 0.041 (3) | 0.049 (3) | 0.051 (3) | 0.012 (2) | 0.011 (2) | 0.009 (2) |
C46 | 0.038 (2) | 0.054 (3) | 0.049 (3) | 0.021 (2) | 0.016 (2) | 0.019 (2) |
C47 | 0.040 (3) | 0.043 (3) | 0.054 (3) | 0.014 (2) | −0.010 (2) | −0.001 (2) |
C48 | 0.043 (3) | 0.038 (3) | 0.050 (3) | 0.017 (2) | 0.007 (2) | 0.005 (2) |
C49 | 0.031 (2) | 0.040 (3) | 0.052 (3) | 0.008 (2) | 0.023 (2) | 0.005 (2) |
C50 | 0.054 (3) | 0.030 (2) | 0.047 (3) | 0.013 (2) | 0.014 (2) | 0.006 (2) |
C51 | 0.038 (3) | 0.056 (3) | 0.052 (3) | 0.015 (2) | 0.012 (2) | 0.010 (2) |
C52 | 0.043 (3) | 0.045 (3) | 0.057 (3) | 0.017 (2) | 0.017 (2) | 0.031 (2) |
Dy1 | 0.04810 (14) | 0.04859 (15) | 0.04748 (14) | 0.01280 (12) | 0.01949 (11) | 0.01889 (11) |
Dy2 | 0.02832 (11) | 0.04888 (15) | 0.05916 (15) | 0.01496 (10) | 0.01314 (10) | 0.00690 (11) |
N1 | 0.048 (2) | 0.037 (2) | 0.060 (3) | 0.008 (2) | 0.011 (2) | 0.027 (2) |
N2 | 0.071 (3) | 0.052 (3) | 0.045 (2) | 0.019 (2) | 0.032 (2) | 0.027 (2) |
N3 | 0.055 (3) | 0.036 (2) | 0.049 (2) | 0.020 (2) | 0.0164 (19) | 0.0164 (18) |
N4 | 0.049 (3) | 0.053 (3) | 0.063 (3) | 0.025 (2) | 0.021 (2) | 0.014 (2) |
N5 | 0.057 (3) | 0.053 (3) | 0.048 (2) | 0.019 (2) | −0.005 (2) | −0.009 (2) |
N6 | 0.032 (2) | 0.057 (3) | 0.046 (2) | 0.011 (2) | −0.0042 (17) | −0.013 (2) |
N7 | 0.057 (3) | 0.058 (3) | 0.048 (3) | 0.019 (3) | 0.010 (2) | 0.007 (2) |
N8 | 0.053 (3) | 0.053 (3) | 0.046 (2) | 0.014 (2) | 0.005 (2) | −0.015 (2) |
N9 | 0.043 (2) | 0.045 (3) | 0.066 (3) | 0.006 (2) | 0.010 (2) | 0.009 (2) |
N10 | 0.038 (2) | 0.048 (3) | 0.057 (2) | 0.0151 (19) | 0.0163 (19) | 0.029 (2) |
N11 | 0.035 (2) | 0.044 (2) | 0.049 (2) | 0.0150 (18) | 0.0192 (17) | 0.0096 (18) |
N12 | 0.054 (3) | 0.051 (3) | 0.044 (2) | 0.016 (2) | −0.0008 (19) | −0.0120 (19) |
N13 | 0.043 (2) | 0.050 (3) | 0.057 (3) | 0.009 (2) | 0.011 (2) | 0.008 (2) |
N14 | 0.045 (2) | 0.037 (2) | 0.0387 (19) | 0.0139 (18) | 0.0148 (16) | 0.0022 (16) |
N15 | 0.050 (3) | 0.034 (2) | 0.049 (2) | 0.016 (2) | −0.005 (2) | −0.0042 (19) |
N16 | 0.040 (2) | 0.030 (2) | 0.045 (2) | 0.0095 (18) | 0.0063 (17) | 0.0066 (17) |
N17 | 0.063 (3) | 0.024 (2) | 0.053 (2) | 0.002 (2) | 0.015 (2) | 0.0093 (18) |
N18 | 0.055 (3) | 0.054 (3) | 0.049 (2) | 0.019 (3) | 0.015 (2) | 0.013 (2) |
O1 | 0.056 (2) | 0.044 (2) | 0.053 (2) | 0.0139 (18) | 0.0120 (17) | 0.0167 (16) |
O2 | 0.056 (2) | 0.058 (3) | 0.052 (2) | 0.016 (2) | −0.0029 (18) | −0.0034 (18) |
O3 | 0.048 (2) | 0.052 (2) | 0.066 (2) | 0.0084 (19) | 0.0002 (18) | 0.0196 (19) |
O4 | 0.048 (2) | 0.043 (2) | 0.0514 (19) | 0.0108 (17) | 0.0169 (16) | 0.0214 (17) |
O5 | 0.056 (2) | 0.052 (2) | 0.051 (2) | 0.0130 (19) | 0.0194 (17) | 0.0093 (17) |
O6 | 0.056 (2) | 0.045 (2) | 0.0489 (19) | 0.0133 (18) | 0.0217 (17) | 0.0146 (16) |
O7 | 0.049 (2) | 0.047 (2) | 0.049 (2) | 0.0067 (18) | 0.0152 (16) | −0.0047 (17) |
O8 | 0.046 (2) | 0.058 (2) | 0.060 (2) | 0.0141 (18) | 0.0161 (17) | 0.0123 (19) |
O9 | 0.0417 (18) | 0.043 (2) | 0.0535 (19) | 0.0170 (16) | 0.0133 (15) | 0.0192 (16) |
O10 | 0.051 (2) | 0.0321 (17) | 0.060 (2) | 0.0260 (16) | 0.0118 (16) | 0.0098 (15) |
O11 | 0.064 (2) | 0.044 (2) | 0.0434 (18) | 0.0184 (19) | 0.0120 (16) | 0.0125 (15) |
O12 | 0.0435 (19) | 0.044 (2) | 0.0459 (18) | 0.0181 (16) | 0.0133 (15) | −0.0010 (15) |
O13 | 0.059 (2) | 0.040 (2) | 0.067 (2) | 0.0138 (19) | 0.0045 (19) | 0.0006 (18) |
O14 | 0.0268 (15) | 0.0415 (18) | 0.0496 (17) | 0.0160 (14) | 0.0104 (13) | −0.0058 (14) |
O15 | 0.0468 (19) | 0.045 (2) | 0.0423 (17) | 0.0196 (17) | 0.0039 (15) | −0.0036 (15) |
O16 | 0.045 (2) | 0.059 (2) | 0.052 (2) | 0.0145 (19) | −0.0167 (17) | −0.0159 (18) |
O17 | 0.059 (2) | 0.046 (2) | 0.053 (2) | −0.0071 (19) | 0.0226 (18) | −0.0012 (17) |
O18 | 0.050 (2) | 0.059 (3) | 0.064 (2) | 0.018 (2) | 0.0196 (18) | −0.0154 (19) |
O19 | 0.059 (2) | 0.053 (2) | 0.057 (2) | 0.017 (2) | 0.0195 (18) | −0.0032 (18) |
O20 | 0.053 (2) | 0.052 (2) | 0.060 (2) | −0.001 (2) | 0.0174 (19) | −0.0151 (19) |
O21 | 0.070 (3) | 0.056 (3) | 0.061 (2) | 0.020 (2) | 0.019 (2) | 0.020 (2) |
O22 | 0.061 (2) | 0.065 (3) | 0.053 (2) | 0.019 (2) | 0.0144 (19) | 0.0162 (19) |
O23 | 0.068 (7) | 0.054 (6) | 0.067 (6) | 0.019 (5) | −0.012 (5) | 0.021 (5) |
O24 | 0.052 (5) | 0.054 (6) | 0.042 (4) | 0.008 (5) | 0.006 (4) | 0.016 (4) |
O25 | 0.065 (6) | 0.054 (6) | 0.057 (5) | 0.022 (5) | −0.015 (5) | 0.024 (5) |
O26 | 0.064 (7) | 0.077 (8) | 0.084 (8) | 0.007 (6) | 0.032 (6) | −0.005 (6) |
O27 | 0.078 (8) | 0.112 (11) | 0.066 (7) | 0.046 (8) | −0.028 (6) | −0.046 (7) |
C1—O1 | 1.358 (4) | C39—C43 | 1.576 (5) |
C1—C2 | 1.390 | C40—C41 | 1.353 (6) |
C1—C6 | 1.390 | C40—H40 | 0.930 |
C2—C3 | 1.390 | C41—C44 | 1.530 (8) |
C2—C7 | 1.396 (6) | C42—N13 | 1.296 (7) |
C3—C4 | 1.390 | C42—H42A | 0.930 |
C3—H3 | 0.930 | C43—H43A | 0.960 |
C4—C5 | 1.390 | C43—H43B | 0.960 |
C4—C8 | 1.526 (6) | C43—H43C | 0.960 |
C5—C6 | 1.390 | C44—N11 | 1.391 (7) |
C5—H5 | 0.930 | C44—N12 | 1.533 (7) |
C6—C9 | 1.498 (6) | C44—H44 | 0.980 |
C7—N1 | 1.328 (5) | C45—C46 | 1.463 (7) |
C7—H7 | 0.930 | C45—N12 | 1.659 (7) |
C8—H8A | 0.960 | C45—H45A | 0.970 |
C8—H8B | 0.960 | C45—H45B | 0.970 |
C8—H8C | 0.960 | C46—N11 | 1.455 (6) |
C9—N2 | 1.244 (6) | C46—H46A | 0.970 |
C9—H9 | 0.930 | C46—H46B | 0.970 |
C10—O2 | 1.346 (4) | C47—N11 | 1.443 (6) |
C10—C11 | 1.390 | C47—C48 | 1.541 (7) |
C10—C15 | 1.390 | C47—H47A | 0.970 |
C11—C12 | 1.390 | C47—H47B | 0.970 |
C11—C16 | 1.474 (7) | C48—N10 | 1.490 (6) |
C12—C13 | 1.390 | C48—H48A | 0.970 |
C12—H12 | 0.930 | C48—H48B | 0.970 |
C13—C14 | 1.390 | C49—N9 | 1.467 (6) |
C13—C17 | 1.542 (6) | C49—C50 | 1.538 (7) |
C14—C15 | 1.390 | C49—H49A | 0.970 |
C14—H14 | 0.930 | C49—H49B | 0.970 |
C15—C18 | 1.546 (5) | C50—N14 | 1.451 (7) |
C16—N4 | 1.259 (7) | C50—H50A | 0.970 |
C16—H16 | 0.930 | C50—H50B | 0.970 |
C17—H17A | 0.960 | C51—N14 | 1.507 (6) |
C17—H17B | 0.960 | C51—C52 | 1.528 (8) |
C17—H17C | 0.960 | C51—H51A | 0.970 |
C18—N5 | 1.425 (6) | C51—H51B | 0.970 |
C18—N6 | 1.501 (6) | C52—N13 | 1.500 (6) |
C18—H18 | 0.980 | C52—H52A | 0.970 |
C19—N1 | 1.490 (5) | C52—H52B | 0.970 |
C19—C20 | 1.519 (8) | Dy1—O2 | 2.265 (4) |
C19—H19A | 0.970 | Dy1—O1 | 2.269 (4) |
C19—H19B | 0.970 | Dy1—O7 | 2.486 (3) |
C20—N6 | 1.475 (6) | Dy1—O4 | 2.525 (3) |
C20—H20A | 0.970 | Dy1—O3 | 2.548 (4) |
C20—H20B | 0.970 | Dy1—N4 | 2.569 (5) |
C21—N6 | 1.495 (5) | Dy1—N3 | 2.578 (4) |
C21—C22 | 1.548 (8) | Dy1—N2 | 2.595 (5) |
C21—H21A | 0.970 | Dy1—O6 | 2.602 (3) |
C21—H21B | 0.970 | Dy2—O10 | 2.270 (3) |
C22—N5 | 1.575 (5) | Dy2—O9 | 2.287 (3) |
C22—H22A | 0.970 | Dy2—O14 | 2.520 (3) |
C22—H22B | 0.970 | Dy2—O12 | 2.538 (3) |
C23—C24 | 1.467 (8) | Dy2—O15 | 2.555 (3) |
C23—N4 | 1.506 (6) | Dy2—N9 | 2.564 (5) |
C23—H23A | 0.970 | Dy2—N13 | 2.571 (5) |
C23—H23B | 0.970 | Dy2—O11 | 2.573 (3) |
C24—N3 | 1.480 (5) | Dy2—N14 | 2.578 (4) |
C24—H24A | 0.970 | N1—H1A | 0.860 |
C24—H24B | 0.970 | N3—H3A | 0.910 |
C25—N3 | 1.463 (6) | N5—H5A | 0.900 |
C25—C26 | 1.513 (8) | N5—H5B | 0.900 |
C25—H25A | 0.970 | N7—O5 | 1.151 (6) |
C25—H25B | 0.970 | N7—O4 | 1.209 (6) |
C26—N2 | 1.475 (6) | N7—O3 | 1.288 (6) |
C26—H26A | 0.970 | N8—O8 | 1.214 (6) |
C26—H26B | 0.970 | N8—O7 | 1.257 (7) |
C27—O9 | 1.291 (5) | N8—O6 | 1.275 (6) |
C27—C28 | 1.401 (7) | N10—H10A | 0.860 |
C27—C32 | 1.415 (7) | N12—H12A | 0.900 |
C28—C29 | 1.408 (7) | N12—H12B | 0.900 |
C28—C33 | 1.460 (7) | N14—H14A | 0.910 |
C29—C30 | 1.385 (7) | N15—O12 | 1.240 (6) |
C29—H29 | 0.930 | N15—O13 | 1.252 (5) |
C30—C31 | 1.414 (7) | N15—O11 | 1.265 (6) |
C30—C34 | 1.507 (7) | N16—O16 | 1.231 (5) |
C31—C32 | 1.416 (8) | N16—O15 | 1.246 (5) |
C31—H31 | 0.930 | N16—O14 | 1.259 (5) |
C32—C35 | 1.379 (7) | N17—O18 | 1.206 (6) |
C33—N9 | 1.289 (6) | N17—O17 | 1.233 (5) |
C33—H33 | 0.930 | N17—O19 | 1.257 (6) |
C34—H34A | 0.960 | N18—O20 | 1.107 (6) |
C34—H34B | 0.960 | N18—O21 | 1.185 (6) |
C34—H34C | 0.960 | N18—O22 | 1.235 (6) |
C35—N10 | 1.321 (5) | O23—H23D | 0.850 |
C35—H35 | 0.930 | O23—H23E | 0.850 |
C36—O10 | 1.276 (6) | O24—H24C | 0.850 |
C36—C37 | 1.421 (8) | O24—H24E | 0.850 |
C36—C41 | 1.431 (6) | O25—H25D | 0.850 |
C37—C42 | 1.411 (5) | O25—H25E | 0.850 |
C37—C38 | 1.442 (7) | O26—H26E | 0.850 |
C38—C39 | 1.343 (8) | O26—H26D | 0.850 |
C38—H38 | 0.930 | O27—H27C | 0.850 |
C39—C40 | 1.400 (8) | O27—H27A | 0.850 |
O1—C1—C2 | 118.6 (2) | N11—C47—H47B | 109.2 |
O1—C1—C6 | 121.2 (2) | C48—C47—H47B | 109.2 |
C2—C1—C6 | 120.0 | H47A—C47—H47B | 107.9 |
C1—C2—C3 | 120.0 | N10—C48—C47 | 109.7 (4) |
C1—C2—C7 | 123.1 (3) | N10—C48—H48A | 109.7 |
C3—C2—C7 | 116.9 (3) | C47—C48—H48A | 109.7 |
C4—C3—C2 | 120.0 | N10—C48—H48B | 109.7 |
C4—C3—H3 | 120.0 | C47—C48—H48B | 109.7 |
C2—C3—H3 | 120.0 | H48A—C48—H48B | 108.2 |
C3—C4—C5 | 120.0 | N9—C49—C50 | 108.3 (4) |
C3—C4—C8 | 119.1 (3) | N9—C49—H49A | 110.0 |
C5—C4—C8 | 120.9 (3) | C50—C49—H49A | 110.0 |
C6—C5—C4 | 120.0 | N9—C49—H49B | 110.0 |
C6—C5—H5 | 120.0 | C50—C49—H49B | 110.0 |
C4—C5—H5 | 120.0 | H49A—C49—H49B | 108.4 |
C5—C6—C1 | 120.0 | N14—C50—C49 | 110.2 (4) |
C5—C6—C9 | 114.8 (3) | N14—C50—H50A | 109.6 |
C1—C6—C9 | 125.1 (3) | C49—C50—H50A | 109.6 |
N1—C7—C2 | 124.9 (4) | N14—C50—H50B | 109.6 |
N1—C7—H7 | 117.5 | C49—C50—H50B | 109.6 |
C2—C7—H7 | 117.5 | H50A—C50—H50B | 108.1 |
C4—C8—H8A | 109.5 | N14—C51—C52 | 109.6 (4) |
C4—C8—H8B | 109.5 | N14—C51—H51A | 109.7 |
H8A—C8—H8B | 109.5 | C52—C51—H51A | 109.7 |
C4—C8—H8C | 109.5 | N14—C51—H51B | 109.7 |
H8A—C8—H8C | 109.5 | C52—C51—H51B | 109.7 |
H8B—C8—H8C | 109.5 | H51A—C51—H51B | 108.2 |
N2—C9—C6 | 126.7 (5) | N13—C52—C51 | 109.2 (4) |
N2—C9—H9 | 116.7 | N13—C52—H52A | 109.8 |
C6—C9—H9 | 116.7 | C51—C52—H52A | 109.8 |
O2—C10—C11 | 122.2 (2) | N13—C52—H52B | 109.8 |
O2—C10—C15 | 117.6 (2) | C51—C52—H52B | 109.8 |
C11—C10—C15 | 120.0 | H52A—C52—H52B | 108.3 |
C12—C11—C10 | 120.0 | O2—Dy1—O1 | 96.09 (15) |
C12—C11—C16 | 115.1 (3) | O2—Dy1—O7 | 124.77 (15) |
C10—C11—C16 | 124.9 (3) | O1—Dy1—O7 | 77.37 (13) |
C11—C12—C13 | 120.0 | O2—Dy1—O4 | 82.30 (14) |
C11—C12—H12 | 120.0 | O1—Dy1—O4 | 121.63 (12) |
C13—C12—H12 | 120.0 | O7—Dy1—O4 | 147.27 (13) |
C12—C13—C14 | 120.0 | O2—Dy1—O3 | 70.77 (14) |
C12—C13—C17 | 121.7 (3) | O1—Dy1—O3 | 74.58 (13) |
C14—C13—C17 | 118.3 (3) | O7—Dy1—O3 | 149.38 (13) |
C15—C14—C13 | 120.0 | O4—Dy1—O3 | 49.67 (12) |
C15—C14—H14 | 120.0 | O2—Dy1—N4 | 72.73 (14) |
C13—C14—H14 | 120.0 | O1—Dy1—N4 | 145.61 (14) |
C14—C15—C10 | 120.0 | O7—Dy1—N4 | 82.75 (14) |
C14—C15—C18 | 119.4 (3) | O4—Dy1—N4 | 89.71 (13) |
C10—C15—C18 | 120.6 (3) | O3—Dy1—N4 | 127.77 (14) |
N4—C16—C11 | 126.8 (5) | O2—Dy1—N3 | 130.87 (14) |
N4—C16—H16 | 116.6 | O1—Dy1—N3 | 133.02 (14) |
C11—C16—H16 | 116.6 | O7—Dy1—N3 | 74.39 (13) |
C13—C17—H17A | 109.5 | O4—Dy1—N3 | 73.54 (12) |
C13—C17—H17B | 109.5 | O3—Dy1—N3 | 117.53 (13) |
H17A—C17—H17B | 109.5 | N4—Dy1—N3 | 65.19 (14) |
C13—C17—H17C | 109.5 | O2—Dy1—N2 | 149.91 (14) |
H17A—C17—H17C | 109.5 | O1—Dy1—N2 | 71.76 (14) |
H17B—C17—H17C | 109.5 | O7—Dy1—N2 | 80.41 (14) |
N5—C18—N6 | 100.7 (4) | O4—Dy1—N2 | 81.32 (12) |
N5—C18—C15 | 112.2 (4) | O3—Dy1—N2 | 79.39 (14) |
N6—C18—C15 | 111.9 (3) | N4—Dy1—N2 | 132.06 (15) |
N5—C18—H18 | 110.5 | N3—Dy1—N2 | 67.11 (14) |
N6—C18—H18 | 110.5 | O2—Dy1—O6 | 75.76 (14) |
C15—C18—H18 | 110.5 | O1—Dy1—O6 | 70.35 (12) |
N1—C19—C20 | 111.3 (4) | O7—Dy1—O6 | 50.09 (13) |
N1—C19—H19A | 109.4 | O4—Dy1—O6 | 156.28 (13) |
C20—C19—H19A | 109.4 | O3—Dy1—O6 | 127.74 (12) |
N1—C19—H19B | 109.4 | N4—Dy1—O6 | 75.35 (13) |
C20—C19—H19B | 109.4 | N3—Dy1—O6 | 114.73 (12) |
H19A—C19—H19B | 108.0 | N2—Dy1—O6 | 122.36 (12) |
N6—C20—C19 | 109.7 (5) | O10—Dy2—O9 | 98.05 (12) |
N6—C20—H20A | 109.7 | O10—Dy2—O14 | 125.75 (11) |
C19—C20—H20A | 109.7 | O9—Dy2—O14 | 74.94 (12) |
N6—C20—H20B | 109.7 | O10—Dy2—O12 | 83.54 (12) |
C19—C20—H20B | 109.7 | O9—Dy2—O12 | 119.82 (12) |
H20A—C20—H20B | 108.2 | O14—Dy2—O12 | 147.03 (10) |
N6—C21—C22 | 100.6 (4) | O10—Dy2—O15 | 76.39 (12) |
N6—C21—H21A | 111.7 | O9—Dy2—O15 | 69.21 (12) |
C22—C21—H21A | 111.7 | O14—Dy2—O15 | 50.44 (10) |
N6—C21—H21B | 111.7 | O12—Dy2—O15 | 159.19 (11) |
C22—C21—H21B | 111.7 | O10—Dy2—N9 | 149.36 (14) |
H21A—C21—H21B | 109.4 | O9—Dy2—N9 | 71.61 (13) |
C21—C22—N5 | 103.5 (3) | O14—Dy2—N9 | 80.44 (13) |
C21—C22—H22A | 111.1 | O12—Dy2—N9 | 77.60 (13) |
N5—C22—H22A | 111.1 | O15—Dy2—N9 | 122.92 (13) |
C21—C22—H22B | 111.1 | O10—Dy2—N13 | 71.20 (14) |
N5—C22—H22B | 111.1 | O9—Dy2—N13 | 145.54 (13) |
H22A—C22—H22B | 109.0 | O14—Dy2—N13 | 85.04 (13) |
C24—C23—N4 | 110.8 (4) | O12—Dy2—N13 | 92.10 (13) |
C24—C23—H23A | 109.5 | O15—Dy2—N13 | 76.39 (13) |
N4—C23—H23A | 109.5 | N9—Dy2—N13 | 132.80 (15) |
C24—C23—H23B | 109.5 | O10—Dy2—O11 | 72.68 (13) |
N4—C23—H23B | 109.5 | O9—Dy2—O11 | 73.55 (12) |
H23A—C23—H23B | 108.1 | O14—Dy2—O11 | 145.53 (12) |
C23—C24—N3 | 109.5 (4) | O12—Dy2—O11 | 49.39 (12) |
C23—C24—H24A | 109.8 | O15—Dy2—O11 | 126.79 (12) |
N3—C24—H24A | 109.8 | N9—Dy2—O11 | 76.71 (14) |
C23—C24—H24B | 109.8 | N13—Dy2—O11 | 129.33 (14) |
N3—C24—H24B | 109.8 | O10—Dy2—N14 | 129.84 (13) |
H24A—C24—H24B | 108.2 | O9—Dy2—N14 | 132.09 (13) |
N3—C25—C26 | 109.5 (4) | O14—Dy2—N14 | 75.68 (11) |
N3—C25—H25A | 109.8 | O12—Dy2—N14 | 73.20 (11) |
C26—C25—H25A | 109.8 | O15—Dy2—N14 | 116.04 (12) |
N3—C25—H25B | 109.8 | N9—Dy2—N14 | 66.83 (14) |
C26—C25—H25B | 109.8 | N13—Dy2—N14 | 66.10 (14) |
H25A—C25—H25B | 108.2 | O11—Dy2—N14 | 117.08 (12) |
N2—C26—C25 | 106.7 (4) | C7—N1—C19 | 121.9 (3) |
N2—C26—H26A | 110.4 | C7—N1—H1A | 119.1 |
C25—C26—H26A | 110.4 | C19—N1—H1A | 119.0 |
N2—C26—H26B | 110.4 | C9—N2—C26 | 117.1 (4) |
C25—C26—H26B | 110.4 | C9—N2—Dy1 | 130.9 (3) |
H26A—C26—H26B | 108.6 | C26—N2—Dy1 | 111.7 (3) |
O9—C27—C28 | 123.0 (4) | C25—N3—C24 | 112.7 (3) |
O9—C27—C32 | 118.8 (4) | C25—N3—Dy1 | 111.6 (2) |
C28—C27—C32 | 118.1 (5) | C24—N3—Dy1 | 110.0 (2) |
C27—C28—C29 | 121.3 (5) | C25—N3—H3A | 107.4 |
C27—C28—C33 | 123.0 (5) | C24—N3—H3A | 107.4 |
C29—C28—C33 | 115.7 (4) | Dy1—N3—H3A | 107.4 |
C30—C29—C28 | 121.0 (4) | C16—N4—C23 | 115.4 (3) |
C30—C29—H29 | 119.5 | C16—N4—Dy1 | 127.2 (3) |
C28—C29—H29 | 119.5 | C23—N4—Dy1 | 117.3 (2) |
C29—C30—C31 | 118.8 (5) | C18—N5—C22 | 104.1 (3) |
C29—C30—C34 | 121.4 (4) | C18—N5—H5A | 110.9 |
C31—C30—C34 | 119.8 (5) | C22—N5—H5A | 110.9 |
C30—C31—C32 | 120.4 (5) | C18—N5—H5B | 110.9 |
C30—C31—H31 | 119.8 | C22—N5—H5B | 110.9 |
C32—C31—H31 | 119.8 | H5A—N5—H5B | 108.9 |
C35—C32—C27 | 124.1 (5) | C20—N6—C21 | 113.7 (3) |
C35—C32—C31 | 115.5 (5) | C20—N6—C18 | 115.4 (3) |
C27—C32—C31 | 120.4 (5) | C21—N6—C18 | 101.1 (3) |
N9—C33—C28 | 128.5 (4) | O5—N7—O4 | 123.9 (5) |
N9—C33—H33 | 115.7 | O5—N7—O3 | 118.9 (5) |
C28—C33—H33 | 115.7 | O4—N7—O3 | 117.2 (4) |
C30—C34—H34A | 109.5 | O8—N8—O7 | 125.0 (5) |
C30—C34—H34B | 109.5 | O8—N8—O6 | 118.0 (5) |
H34A—C34—H34B | 109.5 | O7—N8—O6 | 116.8 (4) |
C30—C34—H34C | 109.5 | C33—N9—C49 | 116.4 (4) |
H34A—C34—H34C | 109.5 | C33—N9—Dy2 | 129.3 (3) |
H34B—C34—H34C | 109.5 | C49—N9—Dy2 | 114.2 (3) |
N10—C35—C32 | 123.4 (4) | C35—N10—C48 | 122.3 (4) |
N10—C35—H35 | 118.3 | C35—N10—H10A | 118.7 |
C32—C35—H35 | 118.3 | C48—N10—H10A | 119.0 |
O10—C36—C37 | 123.3 (5) | C44—N11—C47 | 113.7 (4) |
O10—C36—C41 | 119.8 (4) | C44—N11—C46 | 104.9 (4) |
C37—C36—C41 | 116.8 (5) | C47—N11—C46 | 115.4 (4) |
C42—C37—C36 | 123.2 (4) | C44—N12—C45 | 99.6 (4) |
C42—C37—C38 | 118.5 (5) | C44—N12—H12A | 111.8 |
C36—C37—C38 | 118.3 (5) | C45—N12—H12A | 111.8 |
C39—C38—C37 | 121.9 (6) | C44—N12—H12B | 111.8 |
C39—C38—H38 | 119.0 | C45—N12—H12B | 111.8 |
C37—C38—H38 | 119.0 | H12A—N12—H12B | 109.6 |
C38—C39—C40 | 119.9 (5) | C42—N13—C52 | 115.2 (5) |
C38—C39—C43 | 115.6 (5) | C42—N13—Dy2 | 126.2 (4) |
C40—C39—C43 | 124.4 (5) | C52—N13—Dy2 | 118.2 (3) |
C41—C40—C39 | 120.1 (5) | C50—N14—C51 | 114.0 (4) |
C41—C40—H40 | 119.9 | C50—N14—Dy2 | 114.4 (3) |
C39—C40—H40 | 119.9 | C51—N14—Dy2 | 108.1 (3) |
C40—C41—C36 | 122.7 (4) | C50—N14—H14A | 106.6 |
C40—C41—C44 | 116.9 (4) | C51—N14—H14A | 106.6 |
C36—C41—C44 | 120.3 (4) | Dy2—N14—H14A | 106.6 |
N13—C42—C37 | 127.9 (4) | O12—N15—O13 | 122.0 (4) |
N13—C42—H42A | 116.1 | O12—N15—O11 | 117.0 (4) |
C37—C42—H42A | 116.1 | O13—N15—O11 | 121.0 (5) |
C39—C43—H43A | 109.5 | O16—N16—O15 | 120.7 (4) |
C39—C43—H43B | 109.5 | O16—N16—O14 | 120.0 (4) |
H43A—C43—H43B | 109.5 | O15—N16—O14 | 119.4 (4) |
C39—C43—H43C | 109.5 | O18—N17—O17 | 115.5 (5) |
H43A—C43—H43C | 109.5 | O18—N17—O19 | 117.9 (4) |
H43B—C43—H43C | 109.5 | O17—N17—O19 | 126.3 (5) |
N11—C44—C41 | 116.3 (5) | O20—N18—O21 | 115.5 (5) |
N11—C44—N12 | 100.6 (4) | O20—N18—O22 | 128.0 (5) |
C41—C44—N12 | 107.4 (4) | O21—N18—O22 | 116.4 (5) |
N11—C44—H44 | 110.7 | C1—O1—Dy1 | 143.9 (2) |
C41—C44—H44 | 110.7 | C10—O2—Dy1 | 133.4 (2) |
N12—C44—H44 | 110.7 | N7—O3—Dy1 | 94.4 (3) |
C46—C45—N12 | 102.9 (4) | N7—O4—Dy1 | 97.7 (3) |
C46—C45—H45A | 111.2 | N8—O6—Dy1 | 93.0 (3) |
N12—C45—H45A | 111.2 | N8—O7—Dy1 | 99.0 (3) |
C46—C45—H45B | 111.2 | C27—O9—Dy2 | 144.3 (2) |
N12—C45—H45B | 111.2 | C36—O10—Dy2 | 134.5 (3) |
H45A—C45—H45B | 109.1 | N15—O11—Dy2 | 95.6 (3) |
N11—C46—C45 | 103.9 (4) | N15—O12—Dy2 | 98.0 (3) |
N11—C46—H46A | 111.0 | N16—O14—Dy2 | 93.6 (2) |
C45—C46—H46A | 111.0 | N16—O15—Dy2 | 92.4 (3) |
N11—C46—H46B | 111.0 | H23D—O23—H23E | 109.5 |
C45—C46—H46B | 111.0 | H24C—O24—H24E | 109.5 |
H46A—C46—H46B | 109.0 | H25D—O25—H25E | 109.5 |
N11—C47—C48 | 112.1 (4) | H26E—O26—H26D | 107.3 |
N11—C47—H47A | 109.2 | H27C—O27—H27A | 109.8 |
C48—C47—H47A | 109.2 |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14A···O20 | 0.91 | 2.23 | 3.118 (6) | 166 |
N12—H12B···O10 | 0.90 | 1.99 | 2.696 (6) | 134 |
N12—H12A···N17 | 0.90 | 2.50 | 3.332 (7) | 155 |
N12—H12A···O17 | 0.90 | 2.34 | 2.972 (7) | 127 |
N12—H12A···O18 | 0.90 | 1.91 | 2.786 (6) | 164 |
N5—H5B···O2 | 0.90 | 1.97 | 2.684 (6) | 135 |
N5—H5A···N18 | 0.90 | 2.45 | 3.348 (7) | 177 |
N5—H5A···O21 | 0.90 | 2.21 | 3.015 (7) | 149 |
N5—H5A···O20 | 0.90 | 1.96 | 2.809 (6) | 156 |
N1—H1A···O1 | 0.86 | 1.98 | 2.610 (5) | 130 |
N10—H10A···O9 | 0.86 | 1.99 | 2.620 (5) | 129 |
N3—H3A···O17i | 0.91 | 2.18 | 3.008 (5) | 151 |
Symmetry code: (i) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Dy(C26H34N6O2)(NO3)2]NO3·H2O |
Mr | 829.14 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 14.005 (3), 14.045 (3), 21.896 (4) |
α, β, γ (°) | 96.386 (3), 99.094 (3), 118.217 (3) |
V (Å3) | 3661.0 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.11 |
Crystal size (mm) | 0.30 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.58, 0.66 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36705, 14395, 10889 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.115, 1.04 |
No. of reflections | 14395 |
No. of parameters | 872 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −1.42 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14A···O20 | 0.91 | 2.23 | 3.118 (6) | 165.6 |
N12—H12B···O10 | 0.90 | 1.99 | 2.696 (6) | 133.8 |
N12—H12A···N17 | 0.90 | 2.50 | 3.332 (7) | 154.9 |
N12—H12A···O17 | 0.90 | 2.34 | 2.972 (7) | 126.9 |
N12—H12A···O18 | 0.90 | 1.91 | 2.786 (6) | 163.6 |
N5—H5B···O2 | 0.90 | 1.97 | 2.684 (6) | 135.1 |
N5—H5A···N18 | 0.90 | 2.45 | 3.348 (7) | 177.1 |
N5—H5A···O21 | 0.90 | 2.21 | 3.015 (7) | 149.1 |
N5—H5A···O20 | 0.90 | 1.96 | 2.809 (6) | 155.9 |
N1—H1A···O1 | 0.86 | 1.98 | 2.610 (5) | 129.5 |
N10—H10A···O9 | 0.86 | 1.99 | 2.620 (5) | 128.9 |
N3—H3A···O17i | 0.91 | 2.18 | 3.008 (5) | 150.9 |
Symmetry code: (i) x+1, y+1, z. |
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Lanthanide macrocyclic complexes have received much attention due to their unique properties and many valuable applications such as fluorescent probes in biological systems, material science and chemical processes (Bunzli & Piguet, 2002). Generally, the syntheses of lanthanide macrocyclic complexes are carried out in the presence of a suitable lanthanide ion which acts as a template for macrocycle formation, Most of them are symmetric (Hu et al., 2005). There have been few reports of asymmetric lanthanide complexes.
Recently, Hu et al. (Hu, Qiu et al., 2007; Hu, Chen et al., 2007) have reported the crystal structures of GdIII and LuIII complexes with a macrocyclic ligand derived from 2,6-diformyl-4-methylphenol and 1,5-diamino-3-azapentane: [Gd(C26H34N6O2)(NO3)2]+(NO3)-.H2O and [Lu(C26H34N6O2)(NO3)2]+(NO3)-.0.5H2O.0.25CH3COOC2H5. In these complexes, the central lanthanide ion is nine-coordinate, being bound to five donor atoms from the cyclic polydentate ligand and to four O of two bidentate nitrate anions. Reported here is a new DyIII analogue [Dy(III)(C26H34N6O2)(NO3)2]+(NO3)-.H2O, which exhibits a similar nine-coordinate distorted tricapped trigonal prismatic coordination geometry (Fig. 1 & Fig. 2). The title complex is not isostructural with its GdIII and LuIII analogues. (space groups Cc and C2/c, respectively).