Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103016901/jz1570sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103016901/jz1570Isup2.hkl |
CCDC reference: 226099
Single crystals of [Ba(L)(ClO4)](ClO4), (I), suitable for X-ray crystallography were grown by slow diffusion of diethyl ether into an acetonitrile solution of the previously reported complex Ba(L)(ClO4)2 (Esteban et al., 1999).
Atoms C29 and C30 of the crown moiety were disordered (site occupancy factors 0.593 (10) for C29A and 0.26 (3) for C30A), and 76 similarity restraints were imposed. These restraints were applied to the bonds C28—C29A, C28—C29B, O3—C29A, O3—C29B, O3—C30A, O3—C30B, C30A—C31 and C30B—C31. The positions of all H atoms were calculated geometrically and a riding model was used in their refinement, with C—H distances in the range 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C). Is this added text correct?.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of the cation of (I) with 30% probability displacement ellipsoids. H atoms and the minor disorder component have been omitted for clarity. |
[Ba(ClO4)(C33H41N5O4)](ClO4) | Dx = 1.588 Mg m−3 |
Mr = 907.95 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 6140 reflections |
a = 17.6868 (7) Å | θ = 1.8–28.3° |
b = 20.6923 (8) Å | µ = 1.25 mm−1 |
c = 20.7567 (8) Å | T = 293 K |
V = 7596.5 (5) Å3 | Prism, colourless |
Z = 8 | 0.60 × 0.10 × 0.07 mm |
F(000) = 3680 |
Bruker SMART CCD area-detector diffractometer | 9421 independent reflections |
Radiation source: fine-focus sealed tube | 6140 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ϕ–ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −23→22 |
Tmin = 0.520, Tmax = 0.917 | k = −27→27 |
53172 measured reflections | l = −20→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0141P)2 + 16.3465P] where P = (Fo2 + 2Fc2)/3 |
9421 reflections | (Δ/σ)max = 0.001 |
498 parameters | Δρmax = 0.58 e Å−3 |
76 restraints | Δρmin = −0.47 e Å−3 |
[Ba(ClO4)(C33H41N5O4)](ClO4) | V = 7596.5 (5) Å3 |
Mr = 907.95 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 17.6868 (7) Å | µ = 1.25 mm−1 |
b = 20.6923 (8) Å | T = 293 K |
c = 20.7567 (8) Å | 0.60 × 0.10 × 0.07 mm |
Bruker SMART CCD area-detector diffractometer | 9421 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 6140 reflections with I > 2σ(I) |
Tmin = 0.520, Tmax = 0.917 | Rint = 0.062 |
53172 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 76 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0141P)2 + 16.3465P] where P = (Fo2 + 2Fc2)/3 |
9421 reflections | Δρmax = 0.58 e Å−3 |
498 parameters | Δρmin = −0.47 e Å−3 |
Experimental. Data were collected using a Bruker SMART CCD-based diffractometer operating at room temperature. Data were measured using phi–omega scans of 0.3 degrees per frame for 20 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. 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) | |
Ba1 | 0.695633 (13) | 0.083021 (11) | 0.29307 (1) | 0.03601 (7) | |
Cl1 | 0.83747 (8) | 0.00395 (7) | 0.18978 (8) | 0.0754 (4) | |
Cl2 | 0.54839 (7) | 0.19265 (5) | −0.01173 (5) | 0.0517 (3) | |
N1 | 0.76618 (19) | 0.00035 (17) | 0.39403 (17) | 0.0467 (9) | |
N2 | 0.62103 (18) | −0.04638 (15) | 0.30168 (15) | 0.0379 (7) | |
N3 | 0.61896 (18) | 0.02235 (15) | 0.18423 (15) | 0.0370 (7) | |
N4 | 0.68435 (19) | 0.14327 (15) | 0.16577 (16) | 0.0426 (8) | |
N5 | 0.5982 (2) | 0.2366 (2) | 0.2575 (2) | 0.0616 (11) | |
O1 | 0.72915 (19) | 0.20873 (16) | 0.3316 (2) | 0.0934 (14) | |
O2 | 0.83454 (17) | 0.12090 (15) | 0.35331 (17) | 0.0623 (9) | |
O3 | 0.6330 (2) | 0.0730 (2) | 0.41740 (16) | 0.0876 (13) | |
O4 | 0.54582 (18) | 0.11353 (16) | 0.31822 (17) | 0.0640 (9) | |
O5 | 0.7778 (2) | −0.0265 (2) | 0.2245 (2) | 0.0982 (14) | |
O6 | 0.8342 (2) | 0.06968 (19) | 0.2098 (2) | 0.1026 (14) | |
O7 | 0.9058 (3) | −0.0238 (3) | 0.2077 (3) | 0.158 (2) | |
O8 | 0.8276 (4) | −0.0011 (3) | 0.1254 (2) | 0.174 (3) | |
O9 | 0.5965 (3) | 0.2424 (2) | 0.0088 (2) | 0.1204 (17) | |
O10 | 0.5098 (3) | 0.1691 (2) | 0.0418 (2) | 0.1157 (17) | |
O11 | 0.5921 (2) | 0.14246 (16) | −0.03974 (18) | 0.0773 (11) | |
O12 | 0.5008 (3) | 0.2188 (3) | −0.0581 (2) | 0.1231 (18) | |
C1 | 0.7542 (2) | −0.0696 (2) | 0.3816 (2) | 0.0514 (11) | |
H1A | 0.7913 | −0.0937 | 0.4063 | 0.062* | |
H1B | 0.7644 | −0.0778 | 0.3364 | 0.062* | |
C2 | 0.6772 (2) | −0.09607 (18) | 0.3971 (2) | 0.0456 (10) | |
C3 | 0.6137 (2) | −0.08480 (19) | 0.35876 (19) | 0.0421 (9) | |
C4 | 0.5437 (3) | −0.1102 (2) | 0.3765 (2) | 0.0528 (11) | |
H4 | 0.5011 | −0.1005 | 0.3522 | 0.063* | |
C5 | 0.5372 (3) | −0.1498 (2) | 0.4298 (2) | 0.0631 (13) | |
H5 | 0.4905 | −0.1672 | 0.4408 | 0.076* | |
C6 | 0.5996 (3) | −0.1632 (2) | 0.4664 (2) | 0.0667 (14) | |
H6 | 0.5955 | −0.1903 | 0.5020 | 0.080* | |
C7 | 0.6683 (3) | −0.1367 (2) | 0.4505 (2) | 0.0599 (13) | |
H7 | 0.7101 | −0.1459 | 0.4760 | 0.072* | |
C8 | 0.5863 (2) | −0.06788 (19) | 0.2524 (2) | 0.0460 (10) | |
H8 | 0.5597 | −0.1064 | 0.2565 | 0.055* | |
C9 | 0.5855 (2) | −0.03561 (19) | 0.18937 (19) | 0.0400 (9) | |
C10 | 0.5517 (2) | −0.0667 (2) | 0.1376 (2) | 0.0476 (11) | |
H10 | 0.5279 | −0.1064 | 0.1434 | 0.057* | |
C11 | 0.5538 (2) | −0.0385 (2) | 0.0775 (2) | 0.0504 (11) | |
H11 | 0.5317 | −0.0586 | 0.0422 | 0.060* | |
C12 | 0.5893 (2) | 0.0201 (2) | 0.0713 (2) | 0.0455 (10) | |
H12 | 0.5920 | 0.0403 | 0.0313 | 0.055* | |
C13 | 0.6215 (2) | 0.04910 (18) | 0.12568 (19) | 0.0376 (9) | |
C14 | 0.6594 (2) | 0.11208 (19) | 0.1183 (2) | 0.0427 (10) | |
H14 | 0.6651 | 0.1293 | 0.0772 | 0.051* | |
C15 | 0.7188 (3) | 0.2046 (2) | 0.1518 (2) | 0.0479 (11) | |
C16 | 0.6779 (3) | 0.2611 (2) | 0.1633 (2) | 0.0550 (12) | |
C17 | 0.7111 (4) | 0.3197 (3) | 0.1473 (3) | 0.0819 (18) | |
H17 | 0.6840 | 0.3578 | 0.1528 | 0.098* | |
C18 | 0.7835 (4) | 0.3220 (3) | 0.1232 (3) | 0.100 (2) | |
H18 | 0.8051 | 0.3619 | 0.1137 | 0.120* | |
C19 | 0.8238 (4) | 0.2673 (3) | 0.1130 (3) | 0.090 (2) | |
H19 | 0.8726 | 0.2696 | 0.0967 | 0.108* | |
C20 | 0.7911 (3) | 0.2070 (3) | 0.1274 (3) | 0.0682 (14) | |
H20 | 0.8181 | 0.1691 | 0.1204 | 0.082* | |
C21 | 0.5996 (3) | 0.2581 (2) | 0.1906 (2) | 0.0620 (13) | |
H21A | 0.5768 | 0.3006 | 0.1879 | 0.074* | |
H21B | 0.5694 | 0.2288 | 0.1648 | 0.074* | |
C22 | 0.6362 (3) | 0.2843 (3) | 0.2998 (3) | 0.0762 (16) | |
H22A | 0.6720 | 0.3091 | 0.2746 | 0.091* | |
H22B | 0.5987 | 0.3140 | 0.3167 | 0.091* | |
C23 | 0.6752 (3) | 0.2544 (3) | 0.3528 (3) | 0.0884 (19) | |
H23A | 0.7004 | 0.2875 | 0.3780 | 0.106* | |
H23B | 0.6388 | 0.2330 | 0.3805 | 0.106* | |
C24 | 0.8054 (3) | 0.2270 (2) | 0.3248 (3) | 0.0746 (15) | |
H24A | 0.8114 | 0.2722 | 0.3361 | 0.090* | |
H24B | 0.8212 | 0.2215 | 0.2804 | 0.090* | |
C25 | 0.8518 (3) | 0.1873 (2) | 0.3667 (3) | 0.0715 (15) | |
H25A | 0.9049 | 0.1956 | 0.3588 | 0.086* | |
H25B | 0.8409 | 0.1971 | 0.4115 | 0.086* | |
C26 | 0.8764 (3) | 0.0782 (2) | 0.3930 (3) | 0.0756 (17) | |
H26A | 0.8708 | 0.0906 | 0.4378 | 0.091* | |
H26B | 0.9296 | 0.0805 | 0.3819 | 0.091* | |
C27 | 0.8484 (3) | 0.0107 (2) | 0.3837 (3) | 0.0635 (14) | |
H27A | 0.8607 | −0.0028 | 0.3402 | 0.076* | |
H27B | 0.8758 | −0.0174 | 0.4129 | 0.076* | |
C28 | 0.7420 (3) | 0.0203 (3) | 0.4594 (2) | 0.0664 (14) | |
H28A | 0.7587 | −0.0123 | 0.4897 | 0.080* | |
H28B | 0.7680 | 0.0602 | 0.4702 | 0.080* | |
C29A | 0.6606 (5) | 0.0305 (4) | 0.4686 (4) | 0.061 (3) | 0.593 (10) |
H29A | 0.6342 | −0.0106 | 0.4670 | 0.074* | 0.593 (10) |
H29B | 0.6513 | 0.0500 | 0.5103 | 0.074* | 0.593 (10) |
C29B | 0.6995 (8) | 0.0820 (6) | 0.4647 (6) | 0.075 (4) | 0.407 (10) |
H29C | 0.7307 | 0.1184 | 0.4524 | 0.090* | 0.407 (10) |
H29D | 0.6813 | 0.0886 | 0.5083 | 0.090* | 0.407 (10) |
C30A | 0.5631 (16) | 0.100 (3) | 0.4340 (9) | 0.091 (8) | 0.26 (3) |
H30A | 0.5716 | 0.1403 | 0.4567 | 0.109* | 0.26 (3) |
H30B | 0.5369 | 0.0709 | 0.4631 | 0.109* | 0.26 (3) |
C30B | 0.5526 (5) | 0.0676 (7) | 0.4194 (7) | 0.090 (4) | 0.74 (3) |
H30C | 0.5382 | 0.0243 | 0.4064 | 0.108* | 0.74 (3) |
H30D | 0.5356 | 0.0740 | 0.4634 | 0.108* | 0.74 (3) |
C31 | 0.5166 (3) | 0.1121 (4) | 0.3797 (3) | 0.0912 (19) | |
H31A | 0.4771 | 0.0795 | 0.3800 | 0.109* | |
H31B | 0.4920 | 0.1533 | 0.3869 | 0.109* | |
C32 | 0.5040 (3) | 0.1537 (3) | 0.2725 (3) | 0.0789 (17) | |
H32A | 0.5156 | 0.1394 | 0.2291 | 0.095* | |
H32B | 0.4503 | 0.1475 | 0.2795 | 0.095* | |
C33 | 0.5213 (3) | 0.2221 (3) | 0.2779 (3) | 0.0808 (17) | |
H33A | 0.5148 | 0.2356 | 0.3223 | 0.097* | |
H33B | 0.4861 | 0.2465 | 0.2517 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ba1 | 0.03678 (11) | 0.03728 (11) | 0.03397 (11) | −0.00214 (11) | −0.00420 (11) | −0.00357 (11) |
Cl1 | 0.0685 (9) | 0.0676 (8) | 0.0900 (11) | 0.0017 (7) | 0.0280 (8) | −0.0124 (8) |
Cl2 | 0.0603 (7) | 0.0457 (6) | 0.0491 (6) | 0.0049 (5) | 0.0023 (6) | −0.0016 (5) |
N1 | 0.041 (2) | 0.049 (2) | 0.050 (2) | 0.0019 (17) | −0.0113 (17) | 0.0052 (18) |
N2 | 0.0396 (18) | 0.0371 (17) | 0.0369 (19) | 0.0011 (14) | −0.0037 (15) | 0.0024 (15) |
N3 | 0.0411 (19) | 0.0373 (17) | 0.0325 (17) | −0.0005 (15) | −0.0027 (14) | −0.0007 (14) |
N4 | 0.047 (2) | 0.0404 (18) | 0.0405 (19) | −0.0050 (16) | 0.0006 (16) | 0.0022 (15) |
N5 | 0.043 (2) | 0.071 (3) | 0.071 (3) | 0.006 (2) | −0.001 (2) | −0.009 (2) |
O1 | 0.050 (2) | 0.052 (2) | 0.178 (4) | 0.0069 (17) | −0.032 (2) | −0.041 (3) |
O2 | 0.0517 (19) | 0.0506 (18) | 0.085 (2) | −0.0026 (15) | −0.0276 (18) | 0.0010 (18) |
O3 | 0.084 (3) | 0.134 (4) | 0.0449 (19) | 0.046 (3) | 0.0068 (18) | 0.005 (2) |
O4 | 0.0486 (19) | 0.068 (2) | 0.076 (2) | 0.0114 (17) | 0.0046 (18) | −0.0028 (19) |
O5 | 0.078 (3) | 0.102 (3) | 0.115 (4) | −0.007 (2) | 0.030 (2) | 0.003 (3) |
O6 | 0.090 (3) | 0.078 (3) | 0.139 (4) | −0.001 (2) | 0.016 (3) | −0.028 (3) |
O7 | 0.077 (3) | 0.165 (5) | 0.234 (7) | 0.060 (3) | 0.041 (4) | −0.001 (5) |
O8 | 0.259 (8) | 0.197 (6) | 0.064 (3) | −0.006 (6) | 0.042 (4) | −0.037 (4) |
O9 | 0.127 (4) | 0.097 (3) | 0.137 (4) | −0.041 (3) | 0.007 (3) | −0.047 (3) |
O10 | 0.125 (4) | 0.110 (3) | 0.111 (4) | 0.020 (3) | 0.077 (3) | 0.027 (3) |
O11 | 0.097 (3) | 0.059 (2) | 0.076 (2) | 0.020 (2) | 0.029 (2) | −0.0035 (19) |
O12 | 0.099 (3) | 0.172 (5) | 0.098 (3) | 0.057 (3) | −0.021 (3) | 0.020 (3) |
C1 | 0.050 (3) | 0.046 (3) | 0.058 (3) | 0.010 (2) | −0.008 (2) | 0.004 (2) |
C2 | 0.058 (3) | 0.036 (2) | 0.043 (2) | 0.0049 (19) | −0.002 (2) | 0.0012 (18) |
C3 | 0.053 (2) | 0.0333 (19) | 0.040 (2) | 0.000 (2) | −0.0004 (18) | 0.0019 (19) |
C4 | 0.057 (3) | 0.048 (2) | 0.053 (3) | −0.009 (2) | −0.003 (2) | 0.006 (2) |
C5 | 0.077 (4) | 0.059 (3) | 0.054 (3) | −0.016 (3) | 0.009 (3) | 0.010 (2) |
C6 | 0.100 (4) | 0.054 (3) | 0.046 (3) | −0.003 (3) | 0.008 (3) | 0.013 (2) |
C7 | 0.082 (4) | 0.049 (3) | 0.049 (3) | 0.007 (3) | −0.010 (3) | 0.009 (2) |
C8 | 0.053 (3) | 0.037 (2) | 0.048 (2) | −0.0087 (19) | −0.005 (2) | 0.0019 (19) |
C9 | 0.042 (2) | 0.037 (2) | 0.040 (2) | −0.0028 (18) | −0.0045 (18) | −0.0005 (18) |
C10 | 0.051 (3) | 0.041 (2) | 0.051 (3) | −0.0052 (19) | −0.007 (2) | −0.004 (2) |
C11 | 0.050 (3) | 0.060 (3) | 0.041 (2) | −0.004 (2) | −0.013 (2) | −0.011 (2) |
C12 | 0.047 (2) | 0.055 (3) | 0.035 (2) | 0.002 (2) | −0.0019 (19) | −0.001 (2) |
C13 | 0.036 (2) | 0.039 (2) | 0.038 (2) | 0.0012 (17) | −0.0008 (17) | 0.0000 (18) |
C14 | 0.043 (2) | 0.047 (2) | 0.038 (2) | −0.001 (2) | −0.0020 (19) | 0.006 (2) |
C15 | 0.056 (3) | 0.048 (2) | 0.040 (2) | −0.014 (2) | −0.002 (2) | 0.000 (2) |
C16 | 0.057 (3) | 0.046 (3) | 0.061 (3) | −0.007 (2) | −0.007 (2) | 0.002 (2) |
C17 | 0.099 (5) | 0.047 (3) | 0.100 (5) | −0.013 (3) | −0.001 (4) | 0.003 (3) |
C18 | 0.119 (6) | 0.067 (4) | 0.115 (6) | −0.055 (4) | 0.018 (5) | −0.003 (4) |
C19 | 0.082 (4) | 0.104 (5) | 0.085 (4) | −0.045 (4) | 0.019 (3) | −0.010 (4) |
C20 | 0.064 (3) | 0.071 (3) | 0.069 (3) | −0.016 (3) | 0.015 (3) | −0.004 (3) |
C21 | 0.058 (3) | 0.052 (3) | 0.076 (4) | 0.010 (2) | −0.012 (3) | −0.004 (3) |
C22 | 0.088 (4) | 0.067 (3) | 0.074 (4) | 0.023 (3) | −0.005 (3) | −0.025 (3) |
C23 | 0.083 (4) | 0.069 (3) | 0.113 (5) | 0.012 (3) | −0.023 (4) | −0.036 (4) |
C24 | 0.071 (4) | 0.057 (3) | 0.095 (4) | −0.007 (3) | −0.017 (3) | −0.006 (3) |
C25 | 0.055 (3) | 0.062 (3) | 0.097 (4) | −0.017 (3) | −0.023 (3) | 0.000 (3) |
C26 | 0.046 (3) | 0.071 (3) | 0.110 (5) | −0.009 (3) | −0.035 (3) | 0.018 (3) |
C27 | 0.046 (3) | 0.067 (3) | 0.078 (4) | 0.004 (2) | −0.020 (3) | 0.013 (3) |
C28 | 0.081 (3) | 0.070 (3) | 0.047 (3) | 0.003 (3) | −0.023 (3) | −0.002 (3) |
C29A | 0.080 (5) | 0.070 (6) | 0.035 (4) | −0.001 (5) | 0.001 (4) | −0.007 (4) |
C29B | 0.096 (9) | 0.081 (8) | 0.047 (6) | 0.007 (8) | 0.004 (6) | −0.013 (7) |
C30A | 0.109 (13) | 0.095 (19) | 0.068 (12) | 0.056 (13) | 0.036 (9) | 0.007 (13) |
C30B | 0.113 (6) | 0.066 (6) | 0.092 (7) | 0.036 (5) | 0.063 (5) | 0.013 (5) |
C31 | 0.056 (3) | 0.119 (5) | 0.098 (5) | 0.008 (3) | 0.016 (3) | 0.004 (4) |
C32 | 0.042 (3) | 0.079 (4) | 0.116 (5) | 0.008 (3) | −0.014 (3) | 0.001 (4) |
C33 | 0.056 (3) | 0.087 (4) | 0.099 (5) | 0.019 (3) | 0.007 (3) | 0.009 (4) |
Ba1—O4 | 2.773 (3) | C10—H10 | 0.9300 |
Ba1—O1 | 2.785 (3) | C11—C12 | 1.371 (6) |
Ba1—O3 | 2.816 (3) | C11—H11 | 0.9300 |
Ba1—O2 | 2.866 (3) | C12—C13 | 1.400 (5) |
Ba1—N3 | 2.919 (3) | C12—H12 | 0.9300 |
Ba1—N4 | 2.928 (3) | C13—C14 | 1.474 (5) |
Ba1—N1 | 2.979 (3) | C14—H14 | 0.9300 |
Ba1—N2 | 2.990 (3) | C15—C20 | 1.375 (6) |
Ba1—O6 | 3.012 (4) | C15—C16 | 1.394 (6) |
Ba1—O5 | 3.045 (4) | C16—C17 | 1.388 (7) |
Cl1—O8 | 1.351 (5) | C16—C21 | 1.498 (6) |
Cl1—O7 | 1.388 (5) | C17—C18 | 1.375 (8) |
Cl1—O6 | 1.423 (4) | C17—H17 | 0.9300 |
Cl1—O5 | 1.425 (4) | C18—C19 | 1.354 (9) |
Cl2—O12 | 1.389 (4) | C18—H18 | 0.9300 |
Cl2—O10 | 1.392 (4) | C19—C20 | 1.408 (7) |
Cl2—O9 | 1.402 (4) | C19—H19 | 0.9300 |
Cl2—O11 | 1.419 (3) | C20—H20 | 0.9300 |
N1—C28 | 1.481 (6) | C21—H21A | 0.9700 |
N1—C27 | 1.485 (5) | C21—H21B | 0.9700 |
N1—C1 | 1.486 (5) | C22—C23 | 1.438 (7) |
N2—C8 | 1.274 (5) | C22—H22A | 0.9700 |
N2—C3 | 1.433 (5) | C22—H22B | 0.9700 |
N3—C13 | 1.336 (5) | C23—H23A | 0.9700 |
N3—C9 | 1.342 (5) | C23—H23B | 0.9700 |
N4—C14 | 1.258 (5) | C24—C25 | 1.452 (7) |
N4—C15 | 1.438 (5) | C24—H24A | 0.9700 |
N5—C33 | 1.456 (6) | C24—H24B | 0.9700 |
N5—C21 | 1.457 (6) | C25—H25A | 0.9700 |
N5—C22 | 1.482 (6) | C25—H25B | 0.9700 |
O1—C24 | 1.408 (6) | C26—C27 | 1.495 (6) |
O1—C23 | 1.412 (6) | C26—H26A | 0.9700 |
O2—C26 | 1.417 (5) | C26—H26B | 0.9700 |
O2—C25 | 1.434 (5) | C27—H27A | 0.9700 |
O3—C30A | 1.401 (16) | C27—H27B | 0.9700 |
O3—C30B | 1.428 (9) | C28—C29A | 1.468 (9) |
O3—C29A | 1.463 (8) | C28—C29B | 1.485 (12) |
O3—C29B | 1.543 (12) | C28—H28A | 0.9700 |
O4—C31 | 1.377 (6) | C28—H28B | 0.9700 |
O4—C32 | 1.461 (6) | C29A—H29A | 0.9700 |
C1—C2 | 1.503 (6) | C29A—H29B | 0.9700 |
C1—H1A | 0.9700 | C29B—H29C | 0.9700 |
C1—H1B | 0.9700 | C29B—H29D | 0.9700 |
C2—C3 | 1.397 (6) | C30A—C31 | 1.418 (17) |
C2—C7 | 1.400 (6) | C30A—H30A | 0.9700 |
C3—C4 | 1.393 (6) | C30A—H30B | 0.9700 |
C4—C5 | 1.381 (6) | C30B—C31 | 1.389 (9) |
C4—H4 | 0.9300 | C30B—H30C | 0.9700 |
C5—C6 | 1.369 (7) | C30B—H30D | 0.9700 |
C5—H5 | 0.9300 | C31—H31A | 0.9700 |
C6—C7 | 1.374 (7) | C31—H31B | 0.9700 |
C6—H6 | 0.9300 | C32—C33 | 1.453 (7) |
C7—H7 | 0.9300 | C32—H32A | 0.9700 |
C8—C9 | 1.468 (5) | C32—H32B | 0.9700 |
C8—H8 | 0.9300 | C33—H33A | 0.9700 |
C9—C10 | 1.388 (5) | C33—H33B | 0.9700 |
C10—C11 | 1.377 (6) | ||
O4—Ba1—O1 | 86.37 (10) | C12—C11—C10 | 118.2 (4) |
O4—Ba1—O3 | 57.90 (11) | C12—C11—H11 | 120.9 |
O1—Ba1—O3 | 83.64 (14) | C10—C11—H11 | 120.9 |
O4—Ba1—O2 | 132.42 (10) | C11—C12—C13 | 119.3 (4) |
O1—Ba1—O2 | 55.72 (9) | C11—C12—H12 | 120.4 |
O3—Ba1—O2 | 87.55 (11) | C13—C12—H12 | 120.4 |
O4—Ba1—N3 | 78.45 (10) | N3—C13—C12 | 122.9 (4) |
O1—Ba1—N3 | 136.29 (11) | N3—C13—C14 | 118.4 (4) |
O3—Ba1—N3 | 119.68 (11) | C12—C13—C14 | 118.7 (4) |
O2—Ba1—N3 | 148.61 (9) | N4—C14—C13 | 122.2 (4) |
O4—Ba1—N4 | 90.45 (10) | N4—C14—H14 | 118.9 |
O1—Ba1—N4 | 82.88 (12) | C13—C14—H14 | 118.9 |
O3—Ba1—N4 | 146.26 (10) | C20—C15—C16 | 121.1 (4) |
O2—Ba1—N4 | 109.61 (10) | C20—C15—N4 | 120.0 (4) |
N3—Ba1—N4 | 56.84 (9) | C16—C15—N4 | 119.0 (4) |
O4—Ba1—N1 | 113.48 (10) | C17—C16—C15 | 118.1 (5) |
O1—Ba1—N1 | 104.19 (11) | C17—C16—C21 | 121.2 (5) |
O3—Ba1—N1 | 58.51 (10) | C15—C16—C21 | 120.7 (4) |
O2—Ba1—N1 | 59.41 (9) | C18—C17—C16 | 120.8 (6) |
N3—Ba1—N1 | 119.48 (9) | C18—C17—H17 | 119.6 |
N4—Ba1—N1 | 155.19 (10) | C16—C17—H17 | 119.6 |
O4—Ba1—N2 | 76.77 (9) | C19—C18—C17 | 121.1 (5) |
O1—Ba1—N2 | 155.93 (12) | C19—C18—H18 | 119.4 |
O3—Ba1—N2 | 72.89 (11) | C17—C18—H18 | 119.4 |
O2—Ba1—N2 | 126.66 (9) | C18—C19—C20 | 119.5 (6) |
N3—Ba1—N2 | 57.05 (9) | C18—C19—H19 | 120.3 |
N4—Ba1—N2 | 113.90 (9) | C20—C19—H19 | 120.3 |
N1—Ba1—N2 | 68.20 (9) | C15—C20—C19 | 119.4 (5) |
O4—Ba1—O6 | 154.99 (12) | C15—C20—H20 | 120.3 |
O1—Ba1—O6 | 94.43 (12) | C19—C20—H20 | 120.3 |
O3—Ba1—O6 | 147.07 (12) | N5—C21—C16 | 112.8 (4) |
O2—Ba1—O6 | 65.04 (11) | N5—C21—H21A | 109.0 |
N3—Ba1—O6 | 83.93 (11) | C16—C21—H21A | 109.0 |
N4—Ba1—O6 | 64.94 (11) | N5—C21—H21B | 109.0 |
N1—Ba1—O6 | 90.60 (12) | C16—C21—H21B | 109.0 |
N2—Ba1—O6 | 108.13 (10) | H21A—C21—H21B | 107.8 |
O4—Ba1—O5 | 135.52 (10) | C23—C22—N5 | 112.6 (5) |
O1—Ba1—O5 | 136.68 (11) | C23—C22—H22A | 109.1 |
O3—Ba1—O5 | 124.13 (12) | N5—C22—H22A | 109.1 |
O2—Ba1—O5 | 89.89 (10) | C23—C22—H22B | 109.1 |
N3—Ba1—O5 | 62.62 (10) | N5—C22—H22B | 109.1 |
N4—Ba1—O5 | 85.87 (11) | H22A—C22—H22B | 107.8 |
N1—Ba1—O5 | 72.62 (11) | O1—C23—C22 | 112.0 (5) |
N2—Ba1—O5 | 64.67 (9) | O1—C23—H23A | 109.2 |
O6—Ba1—O5 | 43.54 (10) | C22—C23—H23A | 109.2 |
O8—Cl1—O7 | 110.2 (4) | O1—C23—H23B | 109.2 |
O8—Cl1—O6 | 110.9 (4) | C22—C23—H23B | 109.2 |
O7—Cl1—O6 | 110.6 (3) | H23A—C23—H23B | 107.9 |
O8—Cl1—O5 | 111.8 (4) | O1—C24—C25 | 109.2 (5) |
O7—Cl1—O5 | 109.0 (3) | O1—C24—H24A | 109.8 |
O6—Cl1—O5 | 104.2 (3) | C25—C24—H24A | 109.8 |
O12—Cl2—O10 | 113.1 (3) | O1—C24—H24B | 109.8 |
O12—Cl2—O9 | 106.9 (3) | C25—C24—H24B | 109.8 |
O10—Cl2—O9 | 108.2 (3) | H24A—C24—H24B | 108.3 |
O12—Cl2—O11 | 109.4 (3) | O2—C25—C24 | 107.8 (4) |
O10—Cl2—O11 | 109.7 (2) | O2—C25—H25A | 110.1 |
O9—Cl2—O11 | 109.4 (3) | C24—C25—H25A | 110.1 |
C28—N1—C27 | 112.0 (4) | O2—C25—H25B | 110.1 |
C28—N1—C1 | 113.0 (4) | C24—C25—H25B | 110.1 |
C27—N1—C1 | 104.7 (3) | H25A—C25—H25B | 108.5 |
C28—N1—Ba1 | 111.3 (3) | O2—C26—C27 | 109.6 (4) |
C27—N1—Ba1 | 103.1 (3) | O2—C26—H26A | 109.8 |
C1—N1—Ba1 | 112.2 (2) | C27—C26—H26A | 109.8 |
C8—N2—C3 | 115.3 (3) | O2—C26—H26B | 109.8 |
C8—N2—Ba1 | 118.5 (3) | C27—C26—H26B | 109.8 |
C3—N2—Ba1 | 125.9 (2) | H26A—C26—H26B | 108.2 |
C13—N3—C9 | 117.2 (3) | N1—C27—C26 | 116.1 (4) |
C13—N3—Ba1 | 120.7 (2) | N1—C27—H27A | 108.3 |
C9—N3—Ba1 | 121.9 (2) | C26—C27—H27A | 108.3 |
C14—N4—C15 | 116.3 (3) | N1—C27—H27B | 108.3 |
C14—N4—Ba1 | 120.8 (3) | C26—C27—H27B | 108.3 |
C15—N4—Ba1 | 122.0 (2) | H27A—C27—H27B | 107.4 |
C33—N5—C21 | 110.9 (4) | C29A—C28—N1 | 116.3 (5) |
C33—N5—C22 | 112.8 (4) | N1—C28—C29B | 117.1 (6) |
C21—N5—C22 | 110.8 (4) | C29A—C28—H28A | 108.2 |
C24—O1—C23 | 119.9 (4) | N1—C28—H28A | 108.2 |
C24—O1—Ba1 | 115.2 (3) | C29B—C28—H28A | 134.7 |
C23—O1—Ba1 | 124.8 (3) | C29A—C28—H28B | 108.2 |
C26—O2—C25 | 111.9 (4) | N1—C28—H28B | 108.2 |
C26—O2—Ba1 | 122.1 (3) | C29B—C28—H28B | 59.5 |
C25—O2—Ba1 | 121.9 (3) | H28A—C28—H28B | 107.4 |
C30A—O3—C29A | 110.8 (14) | O3—C29A—C28 | 108.5 (6) |
C30B—O3—C29A | 105.3 (6) | O3—C29A—H29A | 110.0 |
C30A—O3—C29B | 117.9 (15) | C28—C29A—H29A | 110.0 |
C30B—O3—C29B | 138.6 (9) | O3—C29A—H29B | 110.0 |
C30A—O3—Ba1 | 122.9 (10) | C28—C29A—H29B | 110.0 |
C30B—O3—Ba1 | 115.1 (6) | H29A—C29A—H29B | 108.4 |
C29A—O3—Ba1 | 125.4 (4) | C28—C29B—O3 | 103.6 (7) |
C29B—O3—Ba1 | 106.0 (6) | C28—C29B—H29C | 111.0 |
C31—O4—C32 | 115.1 (4) | O3—C29B—H29C | 111.0 |
C31—O4—Ba1 | 121.9 (3) | C28—C29B—H29D | 111.0 |
C32—O4—Ba1 | 119.4 (3) | O3—C29B—H29D | 111.0 |
Cl1—O5—Ba1 | 105.1 (2) | H29C—C29B—H29D | 109.0 |
Cl1—O6—Ba1 | 106.7 (2) | O3—C30A—C31 | 112.8 (13) |
N1—C1—C2 | 116.5 (4) | O3—C30A—H30A | 109.0 |
N1—C1—H1A | 108.2 | C31—C30A—H30A | 109.0 |
C2—C1—H1A | 108.2 | O3—C30A—H30B | 109.0 |
N1—C1—H1B | 108.2 | C31—C30A—H30B | 109.0 |
C2—C1—H1B | 108.2 | H30A—C30A—H30B | 107.8 |
H1A—C1—H1B | 107.3 | C31—C30B—O3 | 112.9 (6) |
C3—C2—C7 | 117.4 (4) | C31—C30B—H30C | 109.0 |
C3—C2—C1 | 123.1 (4) | O3—C30B—H30C | 109.0 |
C7—C2—C1 | 119.4 (4) | C31—C30B—H30D | 109.0 |
C4—C3—C2 | 120.1 (4) | O3—C30B—H30D | 109.0 |
C4—C3—N2 | 120.6 (4) | H30C—C30B—H30D | 107.8 |
C2—C3—N2 | 119.4 (4) | O4—C31—C30B | 113.1 (7) |
C5—C4—C3 | 120.6 (5) | O4—C31—C30A | 121.5 (10) |
C5—C4—H4 | 119.7 | O4—C31—H31A | 107.0 |
C3—C4—H4 | 119.7 | C30B—C31—H31A | 82.4 |
C6—C5—C4 | 119.9 (5) | C30A—C31—H31A | 107.0 |
C6—C5—H5 | 120.0 | O4—C31—H31B | 107.0 |
C4—C5—H5 | 120.0 | C30B—C31—H31B | 134.2 |
C5—C6—C7 | 119.8 (4) | C30A—C31—H31B | 107.0 |
C5—C6—H6 | 120.1 | H31A—C31—H31B | 106.7 |
C7—C6—H6 | 120.1 | C33—C32—O4 | 113.4 (5) |
C6—C7—C2 | 122.1 (5) | C33—C32—H32A | 108.9 |
C6—C7—H7 | 119.0 | O4—C32—H32A | 108.9 |
C2—C7—H7 | 119.0 | C33—C32—H32B | 108.9 |
N2—C8—C9 | 124.1 (4) | O4—C32—H32B | 108.9 |
N2—C8—H8 | 117.9 | H32A—C32—H32B | 107.7 |
C9—C8—H8 | 117.9 | C32—C33—N5 | 112.0 (5) |
N3—C9—C10 | 122.9 (4) | C32—C33—H33A | 109.2 |
N3—C9—C8 | 118.2 (3) | N5—C33—H33A | 109.2 |
C10—C9—C8 | 118.9 (4) | C32—C33—H33B | 109.2 |
C11—C10—C9 | 119.5 (4) | N5—C33—H33B | 109.2 |
C11—C10—H10 | 120.2 | H33A—C33—H33B | 107.9 |
C9—C10—H10 | 120.2 | ||
O4—Ba1—N1—C28 | −39.8 (3) | O5—Ba1—O3—C29B | 80.5 (5) |
O1—Ba1—N1—C28 | 52.4 (3) | O1—Ba1—O4—C31 | −81.0 (4) |
O3—Ba1—N1—C28 | −20.8 (3) | O3—Ba1—O4—C31 | 3.7 (4) |
O2—Ba1—N1—C28 | 86.9 (3) | O2—Ba1—O4—C31 | −46.4 (5) |
N3—Ba1—N1—C28 | −129.5 (3) | N3—Ba1—O4—C31 | 140.2 (4) |
N4—Ba1—N1—C28 | 156.4 (3) | N4—Ba1—O4—C31 | −163.9 (4) |
N2—Ba1—N1—C28 | −103.6 (3) | N1—Ba1—O4—C31 | 22.9 (4) |
O6—Ba1—N1—C28 | 147.1 (3) | N2—Ba1—O4—C31 | 81.6 (4) |
O5—Ba1—N1—C28 | −172.6 (3) | O6—Ba1—O4—C31 | −173.7 (4) |
O4—Ba1—N1—C27 | −160.0 (3) | O5—Ba1—O4—C31 | 111.6 (4) |
O1—Ba1—N1—C27 | −67.8 (3) | O1—Ba1—O4—C32 | 76.3 (3) |
O3—Ba1—N1—C27 | −141.0 (3) | O3—Ba1—O4—C32 | 161.1 (4) |
O2—Ba1—N1—C27 | −33.3 (3) | O2—Ba1—O4—C32 | 111.0 (3) |
N3—Ba1—N1—C27 | 110.3 (3) | N3—Ba1—O4—C32 | −62.5 (3) |
N4—Ba1—N1—C27 | 36.2 (4) | N4—Ba1—O4—C32 | −6.5 (3) |
N2—Ba1—N1—C27 | 136.2 (3) | N1—Ba1—O4—C32 | −179.8 (3) |
O6—Ba1—N1—C27 | 26.9 (3) | N2—Ba1—O4—C32 | −121.0 (3) |
O5—Ba1—N1—C27 | 67.2 (3) | O6—Ba1—O4—C32 | −16.4 (5) |
O4—Ba1—N1—C1 | 87.9 (3) | O5—Ba1—O4—C32 | −91.1 (3) |
O1—Ba1—N1—C1 | −179.9 (3) | O8—Cl1—O5—Ba1 | −113.8 (3) |
O3—Ba1—N1—C1 | 106.9 (3) | O7—Cl1—O5—Ba1 | 124.2 (3) |
O2—Ba1—N1—C1 | −145.4 (3) | O6—Cl1—O5—Ba1 | 6.1 (3) |
N3—Ba1—N1—C1 | −1.8 (3) | O4—Ba1—O5—Cl1 | 139.7 (2) |
N4—Ba1—N1—C1 | −75.9 (4) | O1—Ba1—O5—Cl1 | −21.8 (3) |
N2—Ba1—N1—C1 | 24.1 (3) | O3—Ba1—O5—Cl1 | −143.4 (2) |
O6—Ba1—N1—C1 | −85.2 (3) | O2—Ba1—O5—Cl1 | −56.4 (2) |
O5—Ba1—N1—C1 | −44.9 (3) | N3—Ba1—O5—Cl1 | 107.8 (3) |
O4—Ba1—N2—C8 | 81.9 (3) | N4—Ba1—O5—Cl1 | 53.3 (2) |
O1—Ba1—N2—C8 | 128.6 (3) | N1—Ba1—O5—Cl1 | −114.2 (2) |
O3—Ba1—N2—C8 | 142.0 (3) | N2—Ba1—O5—Cl1 | 172.2 (3) |
O2—Ba1—N2—C8 | −144.6 (3) | O6—Ba1—O5—Cl1 | −4.0 (2) |
N3—Ba1—N2—C8 | −2.8 (3) | O8—Cl1—O6—Ba1 | 114.2 (4) |
N4—Ba1—N2—C8 | −2.7 (3) | O7—Cl1—O6—Ba1 | −123.2 (3) |
N1—Ba1—N2—C8 | −155.8 (3) | O5—Cl1—O6—Ba1 | −6.2 (3) |
O6—Ba1—N2—C8 | −72.6 (3) | O4—Ba1—O6—Cl1 | −97.1 (3) |
O5—Ba1—N2—C8 | −75.4 (3) | O1—Ba1—O6—Cl1 | 171.9 (3) |
O4—Ba1—N2—C3 | −91.3 (3) | O3—Ba1—O6—Cl1 | 86.8 (3) |
O1—Ba1—N2—C3 | −44.6 (4) | O2—Ba1—O6—Cl1 | 123.2 (3) |
O3—Ba1—N2—C3 | −31.2 (3) | N3—Ba1—O6—Cl1 | −51.9 (3) |
O2—Ba1—N2—C3 | 42.2 (3) | N4—Ba1—O6—Cl1 | −108.0 (3) |
N3—Ba1—N2—C3 | −176.0 (3) | N1—Ba1—O6—Cl1 | 67.7 (3) |
N4—Ba1—N2—C3 | −175.8 (3) | N2—Ba1—O6—Cl1 | 0.5 (3) |
N1—Ba1—N2—C3 | 31.0 (3) | O5—Ba1—O6—Cl1 | 4.1 (2) |
O6—Ba1—N2—C3 | 114.2 (3) | C28—N1—C1—C2 | 49.9 (5) |
O5—Ba1—N2—C3 | 111.4 (3) | C27—N1—C1—C2 | 172.0 (4) |
O4—Ba1—N3—C13 | 104.5 (3) | Ba1—N1—C1—C2 | −76.9 (4) |
O1—Ba1—N3—C13 | 32.4 (3) | N1—C1—C2—C3 | 75.1 (5) |
O3—Ba1—N3—C13 | 146.7 (3) | N1—C1—C2—C7 | −108.2 (4) |
O2—Ba1—N3—C13 | −66.2 (3) | C7—C2—C3—C4 | 4.0 (6) |
N4—Ba1—N3—C13 | 6.3 (3) | C1—C2—C3—C4 | −179.2 (4) |
N1—Ba1—N3—C13 | −144.9 (3) | C7—C2—C3—N2 | −176.7 (4) |
N2—Ba1—N3—C13 | −173.9 (3) | C1—C2—C3—N2 | 0.1 (6) |
O6—Ba1—N3—C13 | −57.7 (3) | C8—N2—C3—C4 | −43.5 (5) |
O5—Ba1—N3—C13 | −97.7 (3) | Ba1—N2—C3—C4 | 129.9 (3) |
O4—Ba1—N3—C9 | −81.2 (3) | C8—N2—C3—C2 | 137.2 (4) |
O1—Ba1—N3—C9 | −153.3 (3) | Ba1—N2—C3—C2 | −49.4 (5) |
O3—Ba1—N3—C9 | −39.0 (3) | C2—C3—C4—C5 | −3.8 (7) |
O2—Ba1—N3—C9 | 108.1 (3) | N2—C3—C4—C5 | 176.9 (4) |
N4—Ba1—N3—C9 | −179.4 (3) | C3—C4—C5—C6 | 1.3 (7) |
N1—Ba1—N3—C9 | 29.4 (3) | C4—C5—C6—C7 | 0.9 (8) |
N2—Ba1—N3—C9 | 0.4 (3) | C5—C6—C7—C2 | −0.5 (8) |
O6—Ba1—N3—C9 | 116.6 (3) | C3—C2—C7—C6 | −1.9 (7) |
O5—Ba1—N3—C9 | 76.6 (3) | C1—C2—C7—C6 | −178.8 (4) |
O4—Ba1—N4—C14 | −85.0 (3) | C3—N2—C8—C9 | 179.1 (4) |
O1—Ba1—N4—C14 | −171.3 (3) | Ba1—N2—C8—C9 | 5.2 (5) |
O3—Ba1—N4—C14 | −104.1 (4) | C13—N3—C9—C10 | −2.4 (6) |
O2—Ba1—N4—C14 | 139.0 (3) | Ba1—N3—C9—C10 | −176.9 (3) |
N3—Ba1—N4—C14 | −9.1 (3) | C13—N3—C9—C8 | 176.1 (4) |
N1—Ba1—N4—C14 | 80.2 (4) | Ba1—N3—C9—C8 | 1.6 (5) |
N2—Ba1—N4—C14 | −9.3 (3) | N2—C8—C9—N3 | −4.8 (6) |
O6—Ba1—N4—C14 | 90.4 (3) | N2—C8—C9—C10 | 173.9 (4) |
O5—Ba1—N4—C14 | 50.6 (3) | N3—C9—C10—C11 | 1.7 (7) |
O4—Ba1—N4—C15 | 106.3 (3) | C8—C9—C10—C11 | −176.8 (4) |
O1—Ba1—N4—C15 | 20.0 (3) | C9—C10—C11—C12 | −0.2 (7) |
O3—Ba1—N4—C15 | 87.2 (4) | C10—C11—C12—C13 | −0.5 (6) |
O2—Ba1—N4—C15 | −29.7 (3) | C9—N3—C13—C12 | 1.7 (6) |
N3—Ba1—N4—C15 | −177.8 (3) | Ba1—N3—C13—C12 | 176.3 (3) |
N1—Ba1—N4—C15 | −88.5 (4) | C9—N3—C13—C14 | −178.7 (3) |
N2—Ba1—N4—C15 | −178.0 (3) | Ba1—N3—C13—C14 | −4.1 (5) |
O6—Ba1—N4—C15 | −78.3 (3) | C11—C12—C13—N3 | −0.3 (6) |
O5—Ba1—N4—C15 | −118.1 (3) | C11—C12—C13—C14 | −179.9 (4) |
O4—Ba1—O1—C24 | −175.4 (4) | C15—N4—C14—C13 | −178.9 (4) |
O3—Ba1—O1—C24 | 126.6 (4) | Ba1—N4—C14—C13 | 11.8 (5) |
O2—Ba1—O1—C24 | 35.2 (3) | N3—C13—C14—N4 | −5.2 (6) |
N3—Ba1—O1—C24 | −106.3 (4) | C12—C13—C14—N4 | 174.4 (4) |
N4—Ba1—O1—C24 | −84.4 (4) | C14—N4—C15—C20 | −77.7 (5) |
N1—Ba1—O1—C24 | 71.3 (4) | Ba1—N4—C15—C20 | 91.5 (4) |
N2—Ba1—O1—C24 | 139.4 (4) | C14—N4—C15—C16 | 102.4 (5) |
O6—Ba1—O1—C24 | −20.4 (4) | Ba1—N4—C15—C16 | −88.4 (4) |
O5—Ba1—O1—C24 | −8.2 (5) | C20—C15—C16—C17 | 2.4 (7) |
O4—Ba1—O1—C23 | 0.5 (5) | N4—C15—C16—C17 | −177.6 (4) |
O3—Ba1—O1—C23 | −57.5 (5) | C20—C15—C16—C21 | −179.3 (4) |
O2—Ba1—O1—C23 | −148.9 (5) | N4—C15—C16—C21 | 0.7 (7) |
N3—Ba1—O1—C23 | 69.6 (5) | C15—C16—C17—C18 | −2.8 (9) |
N4—Ba1—O1—C23 | 91.5 (5) | C21—C16—C17—C18 | 178.9 (6) |
N1—Ba1—O1—C23 | −112.8 (5) | C16—C17—C18—C19 | 1.6 (11) |
N2—Ba1—O1—C23 | −44.7 (6) | C17—C18—C19—C20 | −0.1 (11) |
O6—Ba1—O1—C23 | 155.5 (5) | C16—C15—C20—C19 | −0.9 (8) |
O5—Ba1—O1—C23 | 167.7 (4) | N4—C15—C20—C19 | 179.1 (5) |
O4—Ba1—O2—C26 | 106.1 (4) | C18—C19—C20—C15 | −0.3 (9) |
O1—Ba1—O2—C26 | 149.5 (4) | C33—N5—C21—C16 | −168.6 (4) |
O3—Ba1—O2—C26 | 65.5 (4) | C22—N5—C21—C16 | 65.4 (5) |
N3—Ba1—O2—C26 | −86.3 (4) | C17—C16—C21—N5 | −112.5 (5) |
N4—Ba1—O2—C26 | −144.2 (4) | C15—C16—C21—N5 | 69.2 (6) |
N1—Ba1—O2—C26 | 11.1 (4) | C33—N5—C22—C23 | 89.2 (6) |
N2—Ba1—O2—C26 | −0.9 (4) | C21—N5—C22—C23 | −145.9 (5) |
O6—Ba1—O2—C26 | −95.6 (4) | C24—O1—C23—C22 | 95.8 (6) |
O5—Ba1—O2—C26 | −58.6 (4) | Ba1—O1—C23—C22 | −79.9 (6) |
O4—Ba1—O2—C25 | −49.3 (4) | N5—C22—C23—O1 | 56.8 (7) |
O1—Ba1—O2—C25 | −5.9 (4) | C23—O1—C24—C25 | 120.1 (6) |
O3—Ba1—O2—C25 | −89.9 (4) | Ba1—O1—C24—C25 | −63.8 (5) |
N3—Ba1—O2—C25 | 118.3 (4) | C26—O2—C25—C24 | −179.0 (5) |
N4—Ba1—O2—C25 | 60.4 (4) | Ba1—O2—C25—C24 | −21.3 (6) |
N1—Ba1—O2—C25 | −144.3 (4) | O1—C24—C25—O2 | 52.9 (6) |
N2—Ba1—O2—C25 | −156.4 (3) | C25—O2—C26—C27 | 171.9 (5) |
O6—Ba1—O2—C25 | 108.9 (4) | Ba1—O2—C26—C27 | 14.3 (6) |
O5—Ba1—O2—C25 | 145.9 (4) | C28—N1—C27—C26 | −57.4 (6) |
O4—Ba1—O3—C30A | −13 (3) | C1—N1—C27—C26 | 179.8 (4) |
O1—Ba1—O3—C30A | 76 (3) | Ba1—N1—C27—C26 | 62.3 (5) |
O2—Ba1—O3—C30A | 132 (3) | O2—C26—C27—N1 | −55.0 (6) |
N3—Ba1—O3—C30A | −64 (3) | C27—N1—C28—C29A | 162.5 (5) |
N4—Ba1—O3—C30A | 9 (3) | C1—N1—C28—C29A | −79.5 (6) |
N1—Ba1—O3—C30A | −173 (3) | Ba1—N1—C28—C29A | 47.8 (6) |
N2—Ba1—O3—C30A | −98 (3) | C27—N1—C28—C29B | 105.0 (8) |
O6—Ba1—O3—C30A | 165 (3) | C1—N1—C28—C29B | −137.0 (7) |
O5—Ba1—O3—C30A | −140 (3) | Ba1—N1—C28—C29B | −9.8 (8) |
O4—Ba1—O3—C30B | 21.4 (7) | C30A—O3—C29A—C28 | −162 (3) |
O1—Ba1—O3—C30B | 111.1 (7) | C30B—O3—C29A—C28 | 165.8 (9) |
O2—Ba1—O3—C30B | 166.8 (7) | Ba1—O3—C29A—C28 | 28.6 (8) |
N3—Ba1—O3—C30B | −29.6 (7) | N1—C28—C29A—O3 | −50.4 (8) |
N4—Ba1—O3—C30B | 44.1 (8) | N1—C28—C29B—O3 | 54.4 (10) |
N1—Ba1—O3—C30B | −138.0 (7) | C30A—O3—C29B—C28 | 144 (3) |
N2—Ba1—O3—C30B | −63.5 (7) | C30B—O3—C29B—C28 | 114.3 (11) |
O6—Ba1—O3—C30B | −160.6 (7) | Ba1—O3—C29B—C28 | −73.2 (8) |
O5—Ba1—O3—C30B | −105.0 (7) | C29A—O3—C30A—C31 | −149 (3) |
O4—Ba1—O3—C29A | 155.0 (6) | C29B—O3—C30A—C31 | 156 (3) |
O1—Ba1—O3—C29A | −115.3 (5) | Ba1—O3—C30A—C31 | 21 (6) |
O2—Ba1—O3—C29A | −59.5 (5) | C29A—O3—C30B—C31 | 171.4 (11) |
N3—Ba1—O3—C29A | 104.0 (5) | C29B—O3—C30B—C31 | 125.8 (12) |
N4—Ba1—O3—C29A | 177.7 (5) | Ba1—O3—C30B—C31 | −46.3 (15) |
N1—Ba1—O3—C29A | −4.4 (5) | C32—O4—C31—C30B | 172.9 (8) |
N2—Ba1—O3—C29A | 70.1 (5) | Ba1—O4—C31—C30B | −28.8 (10) |
O6—Ba1—O3—C29A | −27.0 (6) | C32—O4—C31—C30A | −153 (3) |
O5—Ba1—O3—C29A | 28.7 (6) | Ba1—O4—C31—C30A | 5 (3) |
O4—Ba1—O3—C29B | −153.2 (6) | O3—C30B—C31—O4 | 49.1 (16) |
O1—Ba1—O3—C29B | −63.5 (5) | O3—C30A—C31—O4 | −17 (5) |
O2—Ba1—O3—C29B | −7.7 (5) | C31—O4—C32—C33 | 80.4 (6) |
N3—Ba1—O3—C29B | 155.8 (5) | Ba1—O4—C32—C33 | −78.5 (5) |
N4—Ba1—O3—C29B | −130.4 (5) | O4—C32—C33—N5 | 68.3 (7) |
N1—Ba1—O3—C29B | 47.5 (5) | C21—N5—C33—C32 | 96.2 (5) |
N2—Ba1—O3—C29B | 122.0 (5) | C22—N5—C33—C32 | −138.9 (5) |
O6—Ba1—O3—C29B | 24.9 (6) |
Experimental details
Crystal data | |
Chemical formula | [Ba(ClO4)(C33H41N5O4)](ClO4) |
Mr | 907.95 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 17.6868 (7), 20.6923 (8), 20.7567 (8) |
V (Å3) | 7596.5 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.25 |
Crystal size (mm) | 0.60 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.520, 0.917 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 53172, 9421, 6140 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.092, 1.07 |
No. of reflections | 9421 |
No. of parameters | 498 |
No. of restraints | 76 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0141P)2 + 16.3465P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.58, −0.47 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXTL (Sheldrick, 1997a), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997b), SHELXTL.
Ba1—O4 | 2.773 (3) | Ba1—N4 | 2.928 (3) |
Ba1—O1 | 2.785 (3) | Ba1—N1 | 2.979 (3) |
Ba1—O3 | 2.816 (3) | Ba1—N2 | 2.990 (3) |
Ba1—O2 | 2.866 (3) | Ba1—O6 | 3.012 (4) |
Ba1—N3 | 2.919 (3) | Ba1—O5 | 3.045 (4) |
O4—Ba1—O1 | 86.37 (10) | O3—Ba1—N2 | 72.89 (11) |
O4—Ba1—O3 | 57.90 (11) | O2—Ba1—N2 | 126.66 (9) |
O1—Ba1—O3 | 83.64 (14) | N3—Ba1—N2 | 57.05 (9) |
O4—Ba1—O2 | 132.42 (10) | N4—Ba1—N2 | 113.90 (9) |
O1—Ba1—O2 | 55.72 (9) | N1—Ba1—N2 | 68.20 (9) |
O3—Ba1—O2 | 87.55 (11) | O4—Ba1—O6 | 154.99 (12) |
O4—Ba1—N3 | 78.45 (10) | O1—Ba1—O6 | 94.43 (12) |
O1—Ba1—N3 | 136.29 (11) | O3—Ba1—O6 | 147.07 (12) |
O3—Ba1—N3 | 119.68 (11) | O2—Ba1—O6 | 65.04 (11) |
O2—Ba1—N3 | 148.61 (9) | N3—Ba1—O6 | 83.93 (11) |
O4—Ba1—N4 | 90.45 (10) | N4—Ba1—O6 | 64.94 (11) |
O1—Ba1—N4 | 82.88 (12) | N1—Ba1—O6 | 90.60 (12) |
O3—Ba1—N4 | 146.26 (10) | N2—Ba1—O6 | 108.13 (10) |
O2—Ba1—N4 | 109.61 (10) | O4—Ba1—O5 | 135.52 (10) |
N3—Ba1—N4 | 56.84 (9) | O1—Ba1—O5 | 136.68 (11) |
O4—Ba1—N1 | 113.48 (10) | O3—Ba1—O5 | 124.13 (12) |
O1—Ba1—N1 | 104.19 (11) | O2—Ba1—O5 | 89.89 (10) |
O3—Ba1—N1 | 58.51 (10) | N3—Ba1—O5 | 62.62 (10) |
O2—Ba1—N1 | 59.41 (9) | N4—Ba1—O5 | 85.87 (11) |
N3—Ba1—N1 | 119.48 (9) | N1—Ba1—O5 | 72.62 (11) |
N4—Ba1—N1 | 155.19 (10) | N2—Ba1—O5 | 64.67 (9) |
O4—Ba1—N2 | 76.77 (9) | O6—Ba1—O5 | 43.54 (10) |
O1—Ba1—N2 | 155.93 (12) |
Macropolycyclic structures delineate molecular cavities into which substrates can penetrate, forming complexes of which the geometry may be regulated via ligand design. According to the number of connecting bridges used for their construction and to the nature of the subunits used as building blocks, a variety of macropolycyclic structures may be envisaged. Lateral macrobicycles are one of these structures, although to date they have been investigated little. They are asymmetrical molecules structurally based on the combination of two different binding units, one chelating and one macrocyclic (Lehn, 1980). We describe herein the X-ray crystal-structure determination of the title barium complex [Ba(L)(ClO4)](ClO4), (I), where L is a Schiff base lateral macrobicycle formed by condensation of the two-armed crown ether N,N'-bis-(2-aminobenzyl)-4,13-diaza-18-crown-6 and 2,6-diformylpyridine. This kind of Schiff base lateral macrobicycle cannot be prepared by a direct reaction between the organic precursors, but BaII is able to template the reaction, thereby allowing the formation of the desired macrobicycles in high yield. In all cases, this metal ion remains trapped in the macrobicycle cavity, giving evidence of its behaviour as a permanent template. \sch
The asymmetric unit of (I) contains the [Ba(L)(ClO4)]+ cation and a well separated perchlorate anion. Fig. 1 shows the structure of the cationic complex, while selected bond lengths and angles are given in Table 1. Unlike its analogue derived from the precursor N,N'-bis-(2-aminobenzyl)-1,10-diaza-15-crown-5, where the BaII ion is coordinated to each donor atom of the macrobicyle (Esteban et al., 1999), in (I) the sequestered BaII ion is only coordinated to eight of the nine available donor atoms of the macrobicycle. The long Ba—N5 distance [3.690 (4) Å] indicates that the pivotal N5 atom does not belong to the coordination sphere of the BaII ion, in spite of its endo conformation with the lone pair directed towards the inside of the cavity. The BaII ion completes its coordination core with two O atoms of one perchlorate group acting as a bidentate ligand. The Ba—O5 and Ba—O6 distances indicate a weak interaction of the BaII ion with the perchlorate group, very often described as `semi-coordination' (Gowda et al., 1984).
The fold of the macrobicyclic receptor around the metal ion allows donor atoms N1, N5, O2 and O4 of the crown moiety to be essentially coplanar [mean deviation from the plane 0.0771 (19) Å], with the BaII ion located 1.032 (2) Å above it. The N3—C13—C14—N4 [−5.2 (6)°] and N3—C9—C8—N2 [−4.8 (6)°] dihedral angles show that the imine groups are not coplanar with the pyridine group, although the loss of planarity is less than that found in the analogue derived from N,N'-bis-(2-aminobenzyl)-1,10-diaza-15-crown-5 (corresponding values of −11.5 and 4.9°). The pyridine ring forms dihedral angles of 83.3 (1)° with the plane containing the benzyl ring attached to the imine atom N4 and of 49.4 (2)° with the plane containing the second aromatic ring. The distance between the two imine atoms (N2 and N4) is 4.961 (4) Å, whereas the distance between the two pivotal atoms (N1 and N5) is 6.384 (4) Å.