Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102016451/av1117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102016451/av1117Isup2.hkl |
CCDC reference: 199403
The title ternary complex was prepared by thoroughly mixing Ba(OH)2·8H2O (1.58 g, 5 mmol), 2-nitrophenol (1.39 g, 10 mmol) and 18-crown-6 (1.32 g, 5 mmol) in ethanol (50 ml). Distilled water (2 mmol Should this be 2 ml?) was then added and the mixture was warmed until a solution was obtained. The solution was filtered and left to evaporate slowly in air. Orange block single crystals of (I) suitable for X-ray data collection were obtained from the solution after a few days.
Rigid regular phenyl groups were fitted for all the phenolate aromatic rings. All H atoms were geometrically fixed with ideal bond lengths and angles, and were treated as riding atoms with Uiso(H) = 1.2Ueq(C, N). Owing to the crystal not being of the best quality, the completeness is less than 0.92. The residual highest peak and deepest hole are 2.47 e Å-3 (0.05 Å from Ba2) and 2.90 e Å-3 (0.94 Å from Ba1), respectively.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
[Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)] | Z = 2 |
Mr = 1427.78 | F(000) = 1448 |
Triclinic, P1 | Dx = 1.597 Mg m−3 |
a = 13.7492 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.9672 (3) Å | Cell parameters from 7466 reflections |
c = 16.8669 (3) Å | θ = 2.5–28.3° |
α = 97.9362 (2)° | µ = 1.41 mm−1 |
β = 109.7546 (7)° | T = 293 K |
γ = 108.8642 (7)° | Block, orange |
V = 2969.6 (1) Å3 | 0.24 × 0.22 × 0.20 mm |
Siemens SMART CCD area-detector diffractometer | 13455 independent reflections |
Radiation source: fine-focus sealed tube | 10337 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
ω scans | h = −11→18 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −19→19 |
Tmin = 0.729, Tmax = 0.766 | l = −22→15 |
17916 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.0328P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
13455 reflections | Δρmax = 2.47 e Å−3 |
692 parameters | Δρmin = −2.90 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0175 (7) |
[Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)] | γ = 108.8642 (7)° |
Mr = 1427.78 | V = 2969.6 (1) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.7492 (3) Å | Mo Kα radiation |
b = 14.9672 (3) Å | µ = 1.41 mm−1 |
c = 16.8669 (3) Å | T = 293 K |
α = 97.9362 (2)° | 0.24 × 0.22 × 0.20 mm |
β = 109.7546 (7)° |
Siemens SMART CCD area-detector diffractometer | 13455 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 10337 reflections with I > 2σ(I) |
Tmin = 0.729, Tmax = 0.766 | Rint = 0.081 |
17916 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 0.96 | Δρmax = 2.47 e Å−3 |
13455 reflections | Δρmin = −2.90 e Å−3 |
692 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
Ba1 | 0.00994 (2) | −0.022354 (19) | 0.250290 (16) | 0.02284 (11) | |
Ba2 | −0.03274 (2) | 0.414640 (19) | 0.243444 (17) | 0.02569 (11) | |
N1 | 0.2253 (4) | 0.2357 (4) | 0.4262 (3) | 0.0406 (11) | |
N2 | −0.2356 (5) | 0.0141 (4) | 0.0846 (3) | 0.0518 (14) | |
N3 | −0.3297 (5) | 0.4673 (4) | 0.0473 (3) | 0.0506 (14) | |
N4 | 0.3601 (4) | 0.7976 (4) | 0.4740 (3) | 0.0451 (12) | |
O1 | 0.0163 (3) | −0.0789 (3) | 0.4117 (2) | 0.0365 (8) | |
O2 | 0.2255 (3) | 0.0223 (3) | 0.4003 (2) | 0.0355 (8) | |
O3 | 0.1996 (3) | −0.0557 (3) | 0.2311 (2) | 0.0418 (9) | |
O4 | 0.0147 (4) | −0.0765 (3) | 0.0811 (2) | 0.0422 (9) | |
O5 | −0.1939 (3) | −0.1764 (3) | 0.0924 (2) | 0.0385 (9) | |
O6 | −0.1802 (3) | −0.1921 (3) | 0.2572 (2) | 0.0395 (9) | |
O7 | 0.0108 (3) | −0.2130 (3) | 0.2371 (3) | 0.0482 (10) | |
H1W1 | −0.0451 | −0.2647 | 0.1931 | 0.072* | |
H2W1 | 0.0673 | −0.2218 | 0.2770 | 0.072* | |
O8 | 0.1372 (3) | 0.1474 (3) | 0.2358 (3) | 0.0453 (10) | |
O9 | 0.1270 (4) | 0.1724 (3) | 0.3930 (3) | 0.0478 (10) | |
O10 | 0.2683 (4) | 0.2850 (4) | 0.5031 (3) | 0.0682 (14) | |
O11 | −0.1345 (3) | 0.0555 (3) | 0.2759 (3) | 0.0436 (9) | |
O12 | −0.1355 (4) | 0.0366 (3) | 0.1152 (3) | 0.0512 (10) | |
O13 | −0.2894 (6) | −0.0031 (6) | 0.0067 (4) | 0.106 (3) | |
O14 | −0.0341 (3) | 0.3823 (3) | 0.4055 (2) | 0.0375 (9) | |
O15 | 0.1715 (3) | 0.4434 (3) | 0.3871 (2) | 0.0364 (8) | |
O16 | 0.1746 (3) | 0.4587 (3) | 0.2256 (2) | 0.0364 (8) | |
O17 | −0.0278 (3) | 0.3499 (3) | 0.0772 (2) | 0.0353 (8) | |
O18 | −0.2357 (3) | 0.3064 (3) | 0.0921 (2) | 0.0358 (8) | |
O19 | −0.2324 (3) | 0.2854 (3) | 0.2528 (3) | 0.0424 (9) | |
O20 | −0.0166 (4) | 0.2386 (3) | 0.2406 (3) | 0.0504 (11) | |
H1W2 | −0.0788 | 0.1838 | 0.2252 | 0.076* | |
H2W2 | 0.0510 | 0.2349 | 0.2549 | 0.076* | |
O21 | −0.1538 (4) | 0.5488 (4) | 0.2217 (3) | 0.0658 (14) | |
O22 | −0.2441 (5) | 0.5154 (4) | 0.0416 (3) | 0.0694 (14) | |
O23 | −0.4053 (5) | 0.3967 (4) | −0.0149 (3) | 0.0827 (18) | |
O24 | 0.0079 (3) | 0.5676 (3) | 0.1566 (2) | 0.0409 (9) | |
H1W3 | −0.0314 | 0.6059 | 0.1522 | 0.061* | |
H2W3 | 0.0598 | 0.5770 | 0.1339 | 0.061* | |
O25 | 0.0383 (3) | 0.6025 (3) | 0.3634 (2) | 0.0389 (9) | |
H1W4 | −0.0034 | 0.6385 | 0.3519 | 0.058* | |
H2W4 | 0.1022 | 0.6252 | 0.4125 | 0.058* | |
O26 | 0.1824 (3) | 0.7160 (3) | 0.2995 (3) | 0.0423 (9) | |
O27 | 0.2708 (4) | 0.7563 (4) | 0.4771 (3) | 0.0726 (16) | |
O28 | 0.4388 (4) | 0.8640 (5) | 0.5382 (3) | 0.0865 (18) | |
C1 | 0.1213 (5) | −0.0735 (5) | 0.4741 (4) | 0.0432 (14) | |
H1A | 0.1354 | −0.1304 | 0.4548 | 0.052* | |
H1B | 0.1184 | −0.0726 | 0.5308 | 0.052* | |
C2 | 0.2131 (5) | 0.0184 (5) | 0.4809 (3) | 0.0447 (14) | |
H2A | 0.1980 | 0.0744 | 0.5009 | 0.054* | |
H2B | 0.2838 | 0.0241 | 0.5248 | 0.054* | |
C3 | 0.2910 (4) | −0.0295 (4) | 0.3835 (4) | 0.0395 (13) | |
H3A | 0.2522 | −0.0991 | 0.3752 | 0.047* | |
H3B | 0.3633 | −0.0058 | 0.4331 | 0.047* | |
C4 | 0.3080 (5) | −0.0130 (5) | 0.3029 (4) | 0.0428 (13) | |
H4A | 0.3429 | 0.0568 | 0.3097 | 0.051* | |
H4B | 0.3564 | −0.0438 | 0.2926 | 0.051* | |
C5 | 0.2035 (6) | −0.0586 (5) | 0.1473 (4) | 0.0538 (17) | |
H5A | 0.2573 | −0.0856 | 0.1426 | 0.065* | |
H5B | 0.2284 | 0.0076 | 0.1414 | 0.065* | |
C6 | 0.0948 (5) | −0.1177 (5) | 0.0783 (4) | 0.0492 (15) | |
H6A | 0.0696 | −0.1838 | 0.0845 | 0.059* | |
H6B | 0.0999 | −0.1215 | 0.0221 | 0.059* | |
C7 | −0.0956 (5) | −0.1236 (5) | 0.0055 (4) | 0.0470 (15) | |
H7A | −0.1297 | −0.0763 | −0.0037 | 0.056* | |
H7B | −0.0851 | −0.1450 | −0.0469 | 0.056* | |
C8 | −0.1698 (6) | −0.2075 (5) | 0.0200 (4) | 0.0518 (16) | |
H8A | −0.2394 | −0.2408 | −0.0322 | 0.062* | |
H8B | −0.1344 | −0.2535 | 0.0318 | 0.062* | |
C9 | −0.2757 (5) | −0.2570 (4) | 0.1039 (4) | 0.0463 (14) | |
H9A | −0.2517 | −0.3112 | 0.1061 | 0.056* | |
H9B | −0.3479 | −0.2797 | 0.0543 | 0.056* | |
C10 | −0.2879 (4) | −0.2249 (4) | 0.1865 (4) | 0.0394 (12) | |
H10A | −0.3141 | −0.1720 | 0.1841 | 0.047* | |
H10B | −0.3421 | −0.2793 | 0.1945 | 0.047* | |
C11 | −0.1827 (5) | −0.1704 (5) | 0.3411 (4) | 0.0428 (14) | |
H11A | −0.2451 | −0.2223 | 0.3434 | 0.051* | |
H11B | −0.1924 | −0.1092 | 0.3524 | 0.051* | |
C12 | −0.0727 (5) | −0.1618 (5) | 0.4091 (4) | 0.0409 (13) | |
H12A | −0.0757 | −0.1548 | 0.4662 | 0.049* | |
H12B | −0.0599 | −0.2208 | 0.3944 | 0.049* | |
C13 | −0.2445 (2) | 0.0316 (3) | 0.2310 (2) | 0.0355 (11) | |
C14 | −0.3076 (3) | 0.0297 (3) | 0.28049 (19) | 0.0488 (15) | |
H14 | −0.2722 | 0.0484 | 0.3414 | 0.059* | |
C15 | −0.4236 (3) | 0.0001 (4) | 0.2390 (3) | 0.071 (2) | |
H15 | −0.4658 | −0.0012 | 0.2721 | 0.085* | |
C16 | −0.4765 (2) | −0.0278 (4) | 0.1480 (3) | 0.078 (3) | |
H16 | −0.5541 | −0.0476 | 0.1202 | 0.094* | |
C17 | −0.4133 (3) | −0.0260 (3) | 0.0985 (2) | 0.0565 (17) | |
H17 | −0.4487 | −0.0446 | 0.0376 | 0.068* | |
C18 | −0.2973 (3) | 0.0037 (3) | 0.1400 (2) | 0.0384 (12) | |
C19 | 0.2466 (2) | 0.2082 (2) | 0.2851 (2) | 0.0353 (11) | |
C20 | 0.3160 (3) | 0.2276 (3) | 0.2404 (2) | 0.0481 (15) | |
H20 | 0.2871 | 0.1982 | 0.1805 | 0.058* | |
C21 | 0.4287 (3) | 0.2910 (4) | 0.2852 (3) | 0.065 (2) | |
H21 | 0.4752 | 0.3040 | 0.2553 | 0.078* | |
C22 | 0.4720 (2) | 0.3350 (4) | 0.3747 (3) | 0.078 (3) | |
H22 | 0.5474 | 0.3774 | 0.4047 | 0.094* | |
C23 | 0.4026 (3) | 0.3155 (3) | 0.4194 (2) | 0.0596 (18) | |
H23 | 0.4316 | 0.3450 | 0.4793 | 0.072* | |
C24 | 0.2899 (3) | 0.2521 (3) | 0.3746 (2) | 0.0355 (11) | |
C25 | 0.0650 (5) | 0.3876 (5) | 0.4694 (4) | 0.0475 (15) | |
H25A | 0.0722 | 0.3253 | 0.4578 | 0.057* | |
H25B | 0.0626 | 0.4005 | 0.5265 | 0.057* | |
C26 | 0.1658 (5) | 0.4690 (5) | 0.4696 (4) | 0.0470 (15) | |
H26A | 0.1573 | 0.5310 | 0.4781 | 0.056* | |
H26B | 0.2343 | 0.4759 | 0.5168 | 0.056* | |
C27 | 0.2698 (5) | 0.5131 (4) | 0.3826 (4) | 0.0434 (13) | |
H27A | 0.3372 | 0.5223 | 0.4323 | 0.052* | |
H27B | 0.2640 | 0.5761 | 0.3841 | 0.052* | |
C28 | 0.2764 (5) | 0.4740 (4) | 0.2997 (4) | 0.0407 (13) | |
H28A | 0.3412 | 0.5201 | 0.2951 | 0.049* | |
H28B | 0.2853 | 0.4123 | 0.2995 | 0.049* | |
C29 | 0.1711 (6) | 0.4117 (5) | 0.1450 (4) | 0.0503 (16) | |
H29A | 0.1650 | 0.3451 | 0.1440 | 0.060* | |
H29B | 0.2401 | 0.4470 | 0.1392 | 0.060* | |
C30 | 0.0742 (5) | 0.4096 (5) | 0.0716 (4) | 0.0409 (13) | |
H30A | 0.0779 | 0.4758 | 0.0741 | 0.049* | |
H30B | 0.0752 | 0.3824 | 0.0163 | 0.049* | |
C31 | −0.1273 (6) | 0.3452 (5) | 0.0085 (3) | 0.0448 (14) | |
H31A | −0.1255 | 0.3258 | −0.0481 | 0.054* | |
H31B | −0.1311 | 0.4092 | 0.0158 | 0.054* | |
C32 | −0.2258 (5) | 0.2733 (5) | 0.0128 (4) | 0.0473 (15) | |
H32A | −0.2931 | 0.2637 | −0.0370 | 0.057* | |
H32B | −0.2185 | 0.2107 | 0.0103 | 0.057* | |
C33 | −0.3306 (5) | 0.2357 (4) | 0.0983 (4) | 0.0474 (14) | |
H33A | −0.3241 | 0.1727 | 0.0934 | 0.057* | |
H33B | −0.3994 | 0.2274 | 0.0506 | 0.057* | |
C34 | −0.3351 (5) | 0.2696 (5) | 0.1840 (4) | 0.0466 (14) | |
H34A | −0.3472 | 0.3301 | 0.1873 | 0.056* | |
H34B | −0.3971 | 0.2204 | 0.1893 | 0.056* | |
C35 | −0.2347 (5) | 0.3011 (5) | 0.3367 (4) | 0.0460 (14) | |
H35A | −0.2999 | 0.2496 | 0.3360 | 0.055* | |
H35B | −0.2394 | 0.3638 | 0.3532 | 0.055* | |
C36 | −0.1304 (6) | 0.3003 (5) | 0.4001 (4) | 0.0487 (15) | |
H36A | −0.1327 | 0.3054 | 0.4574 | 0.058* | |
H36B | −0.1239 | 0.2390 | 0.3815 | 0.058* | |
C37 | −0.2601 (2) | 0.5343 (3) | 0.2081 (2) | 0.0407 (13) | |
C38 | −0.2836 (3) | 0.5573 (3) | 0.2804 (2) | 0.0502 (15) | |
H38 | −0.2255 | 0.5853 | 0.3361 | 0.060* | |
C39 | −0.3939 (4) | 0.5386 (4) | 0.2693 (3) | 0.066 (2) | |
H39 | −0.4096 | 0.5540 | 0.3177 | 0.079* | |
C40 | −0.4807 (3) | 0.4968 (4) | 0.1860 (3) | 0.079 (3) | |
H40 | −0.5545 | 0.4842 | 0.1786 | 0.095* | |
C41 | −0.4572 (3) | 0.4737 (3) | 0.1137 (2) | 0.0585 (18) | |
H41 | −0.5153 | 0.4457 | 0.0579 | 0.070* | |
C42 | −0.3469 (3) | 0.4925 (3) | 0.1247 (2) | 0.0398 (13) | |
C43 | 0.2894 (2) | 0.7333 (3) | 0.3130 (2) | 0.0340 (11) | |
C44 | 0.3127 (3) | 0.7111 (3) | 0.24047 (18) | 0.0506 (15) | |
H44 | 0.2545 | 0.6836 | 0.1847 | 0.061* | |
C45 | 0.4229 (4) | 0.7300 (4) | 0.2512 (3) | 0.076 (2) | |
H45 | 0.4385 | 0.7152 | 0.2027 | 0.091* | |
C46 | 0.5099 (3) | 0.7712 (4) | 0.3345 (3) | 0.074 (2) | |
H46 | 0.5836 | 0.7838 | 0.3417 | 0.089* | |
C47 | 0.4866 (2) | 0.7934 (4) | 0.4071 (2) | 0.0545 (17) | |
H47 | 0.5447 | 0.8209 | 0.4628 | 0.065* | |
C48 | 0.3763 (3) | 0.7744 (3) | 0.39634 (19) | 0.0365 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ba1 | 0.02353 (17) | 0.02290 (16) | 0.02523 (16) | 0.01037 (12) | 0.01214 (12) | 0.00759 (11) |
Ba2 | 0.03054 (19) | 0.02262 (16) | 0.02452 (16) | 0.00905 (13) | 0.01297 (12) | 0.00757 (11) |
N1 | 0.044 (3) | 0.042 (3) | 0.039 (2) | 0.018 (2) | 0.017 (2) | 0.018 (2) |
N2 | 0.074 (4) | 0.058 (4) | 0.039 (3) | 0.042 (3) | 0.022 (3) | 0.023 (2) |
N3 | 0.055 (4) | 0.047 (3) | 0.046 (3) | 0.030 (3) | 0.008 (3) | 0.011 (2) |
N4 | 0.044 (3) | 0.044 (3) | 0.046 (3) | 0.016 (2) | 0.018 (2) | 0.014 (2) |
O1 | 0.034 (2) | 0.046 (2) | 0.0339 (19) | 0.0151 (18) | 0.0165 (16) | 0.0204 (17) |
O2 | 0.038 (2) | 0.040 (2) | 0.0349 (19) | 0.0186 (18) | 0.0167 (16) | 0.0155 (16) |
O3 | 0.032 (2) | 0.054 (3) | 0.043 (2) | 0.0161 (19) | 0.0209 (17) | 0.0119 (18) |
O4 | 0.053 (3) | 0.046 (2) | 0.0326 (19) | 0.022 (2) | 0.0221 (18) | 0.0062 (17) |
O5 | 0.047 (2) | 0.029 (2) | 0.0335 (19) | 0.0088 (18) | 0.0172 (17) | 0.0057 (15) |
O6 | 0.0276 (19) | 0.042 (2) | 0.042 (2) | 0.0031 (17) | 0.0187 (16) | 0.0074 (17) |
O7 | 0.041 (2) | 0.034 (2) | 0.075 (3) | 0.0168 (19) | 0.026 (2) | 0.019 (2) |
O8 | 0.046 (2) | 0.033 (2) | 0.045 (2) | 0.0028 (18) | 0.0185 (19) | 0.0074 (17) |
O9 | 0.044 (2) | 0.053 (3) | 0.056 (3) | 0.016 (2) | 0.031 (2) | 0.023 (2) |
O10 | 0.074 (4) | 0.084 (4) | 0.038 (2) | 0.022 (3) | 0.024 (2) | 0.009 (2) |
O11 | 0.032 (2) | 0.054 (3) | 0.048 (2) | 0.022 (2) | 0.0151 (18) | 0.0152 (19) |
O12 | 0.053 (3) | 0.049 (3) | 0.054 (3) | 0.019 (2) | 0.026 (2) | 0.015 (2) |
O13 | 0.103 (5) | 0.202 (8) | 0.051 (3) | 0.097 (6) | 0.034 (3) | 0.058 (4) |
O14 | 0.045 (2) | 0.041 (2) | 0.0332 (19) | 0.0167 (19) | 0.0217 (17) | 0.0183 (16) |
O15 | 0.041 (2) | 0.037 (2) | 0.0291 (18) | 0.0118 (18) | 0.0162 (16) | 0.0090 (15) |
O16 | 0.038 (2) | 0.041 (2) | 0.0367 (19) | 0.0189 (18) | 0.0194 (17) | 0.0119 (16) |
O17 | 0.048 (2) | 0.035 (2) | 0.0286 (17) | 0.0206 (18) | 0.0171 (16) | 0.0111 (15) |
O18 | 0.036 (2) | 0.029 (2) | 0.0340 (19) | 0.0080 (17) | 0.0113 (16) | 0.0069 (15) |
O19 | 0.032 (2) | 0.054 (3) | 0.044 (2) | 0.0121 (19) | 0.0208 (18) | 0.0191 (19) |
O20 | 0.055 (3) | 0.024 (2) | 0.077 (3) | 0.0161 (19) | 0.031 (2) | 0.0160 (19) |
O21 | 0.032 (2) | 0.100 (4) | 0.054 (3) | 0.027 (3) | 0.011 (2) | 0.002 (3) |
O22 | 0.077 (4) | 0.074 (4) | 0.070 (3) | 0.033 (3) | 0.042 (3) | 0.018 (3) |
O23 | 0.073 (4) | 0.068 (4) | 0.065 (3) | 0.033 (3) | −0.014 (3) | −0.012 (3) |
O24 | 0.046 (2) | 0.037 (2) | 0.047 (2) | 0.0191 (19) | 0.0255 (19) | 0.0088 (17) |
O25 | 0.034 (2) | 0.041 (2) | 0.0360 (19) | 0.0105 (17) | 0.0110 (16) | 0.0121 (16) |
O26 | 0.0226 (19) | 0.042 (2) | 0.052 (2) | 0.0057 (17) | 0.0086 (17) | 0.0147 (18) |
O27 | 0.042 (3) | 0.091 (4) | 0.053 (3) | −0.011 (3) | 0.025 (2) | 0.001 (3) |
O28 | 0.058 (3) | 0.097 (5) | 0.054 (3) | −0.001 (3) | 0.009 (3) | −0.013 (3) |
C1 | 0.033 (3) | 0.051 (4) | 0.038 (3) | 0.010 (3) | 0.008 (2) | 0.022 (3) |
C2 | 0.043 (3) | 0.052 (4) | 0.028 (3) | 0.011 (3) | 0.008 (2) | 0.013 (2) |
C3 | 0.024 (3) | 0.038 (3) | 0.050 (3) | 0.013 (2) | 0.006 (2) | 0.011 (2) |
C4 | 0.026 (3) | 0.046 (3) | 0.059 (4) | 0.014 (3) | 0.021 (3) | 0.013 (3) |
C5 | 0.054 (4) | 0.065 (4) | 0.057 (4) | 0.022 (3) | 0.042 (3) | 0.013 (3) |
C6 | 0.050 (4) | 0.058 (4) | 0.046 (3) | 0.023 (3) | 0.029 (3) | 0.003 (3) |
C7 | 0.052 (4) | 0.059 (4) | 0.028 (3) | 0.019 (3) | 0.019 (3) | 0.009 (3) |
C8 | 0.058 (4) | 0.046 (4) | 0.033 (3) | 0.010 (3) | 0.014 (3) | −0.006 (3) |
C9 | 0.049 (4) | 0.026 (3) | 0.046 (3) | 0.002 (3) | 0.013 (3) | 0.002 (2) |
C10 | 0.031 (3) | 0.032 (3) | 0.051 (3) | 0.006 (2) | 0.017 (2) | 0.013 (2) |
C11 | 0.036 (3) | 0.050 (4) | 0.047 (3) | 0.009 (3) | 0.031 (3) | 0.016 (3) |
C12 | 0.042 (3) | 0.051 (4) | 0.044 (3) | 0.017 (3) | 0.029 (3) | 0.029 (3) |
C13 | 0.034 (3) | 0.028 (3) | 0.049 (3) | 0.013 (2) | 0.020 (2) | 0.017 (2) |
C14 | 0.053 (4) | 0.057 (4) | 0.045 (3) | 0.022 (3) | 0.026 (3) | 0.024 (3) |
C15 | 0.039 (4) | 0.090 (6) | 0.091 (6) | 0.018 (4) | 0.037 (4) | 0.035 (5) |
C16 | 0.016 (3) | 0.082 (6) | 0.107 (7) | 0.004 (3) | 0.004 (4) | 0.034 (5) |
C17 | 0.046 (4) | 0.053 (4) | 0.051 (4) | 0.012 (3) | 0.003 (3) | 0.021 (3) |
C18 | 0.040 (3) | 0.034 (3) | 0.046 (3) | 0.017 (3) | 0.018 (3) | 0.018 (2) |
C19 | 0.035 (3) | 0.027 (3) | 0.048 (3) | 0.010 (2) | 0.021 (2) | 0.019 (2) |
C20 | 0.055 (4) | 0.049 (4) | 0.054 (4) | 0.021 (3) | 0.035 (3) | 0.024 (3) |
C21 | 0.047 (4) | 0.081 (5) | 0.082 (5) | 0.020 (4) | 0.043 (4) | 0.040 (4) |
C22 | 0.026 (3) | 0.098 (7) | 0.078 (5) | −0.006 (4) | 0.012 (3) | 0.025 (5) |
C23 | 0.043 (4) | 0.065 (5) | 0.052 (4) | 0.006 (3) | 0.012 (3) | 0.016 (3) |
C24 | 0.035 (3) | 0.037 (3) | 0.040 (3) | 0.015 (2) | 0.017 (2) | 0.020 (2) |
C25 | 0.050 (4) | 0.064 (4) | 0.035 (3) | 0.023 (3) | 0.021 (3) | 0.026 (3) |
C26 | 0.047 (4) | 0.058 (4) | 0.026 (3) | 0.015 (3) | 0.010 (2) | 0.009 (3) |
C27 | 0.035 (3) | 0.038 (3) | 0.042 (3) | 0.001 (3) | 0.011 (2) | 0.011 (2) |
C28 | 0.030 (3) | 0.045 (3) | 0.045 (3) | 0.011 (3) | 0.014 (2) | 0.019 (3) |
C29 | 0.057 (4) | 0.062 (4) | 0.053 (4) | 0.035 (4) | 0.036 (3) | 0.018 (3) |
C30 | 0.053 (4) | 0.048 (3) | 0.038 (3) | 0.024 (3) | 0.033 (3) | 0.016 (2) |
C31 | 0.062 (4) | 0.053 (4) | 0.026 (3) | 0.031 (3) | 0.017 (3) | 0.014 (2) |
C32 | 0.054 (4) | 0.043 (4) | 0.033 (3) | 0.014 (3) | 0.013 (3) | 0.001 (2) |
C33 | 0.044 (4) | 0.036 (3) | 0.056 (4) | 0.011 (3) | 0.017 (3) | 0.015 (3) |
C34 | 0.040 (3) | 0.042 (3) | 0.065 (4) | 0.014 (3) | 0.028 (3) | 0.024 (3) |
C35 | 0.039 (3) | 0.053 (4) | 0.050 (3) | 0.012 (3) | 0.028 (3) | 0.014 (3) |
C36 | 0.065 (4) | 0.048 (4) | 0.042 (3) | 0.016 (3) | 0.036 (3) | 0.021 (3) |
C37 | 0.029 (3) | 0.041 (3) | 0.046 (3) | 0.013 (3) | 0.010 (2) | 0.010 (2) |
C38 | 0.042 (4) | 0.049 (4) | 0.059 (4) | 0.015 (3) | 0.021 (3) | 0.019 (3) |
C39 | 0.067 (5) | 0.078 (5) | 0.081 (5) | 0.033 (4) | 0.052 (4) | 0.041 (4) |
C40 | 0.030 (4) | 0.105 (7) | 0.107 (7) | 0.022 (4) | 0.033 (4) | 0.046 (6) |
C41 | 0.029 (3) | 0.052 (4) | 0.076 (5) | 0.006 (3) | 0.006 (3) | 0.025 (3) |
C42 | 0.027 (3) | 0.026 (3) | 0.060 (4) | 0.010 (2) | 0.010 (2) | 0.016 (2) |
C43 | 0.028 (3) | 0.029 (3) | 0.046 (3) | 0.010 (2) | 0.014 (2) | 0.019 (2) |
C44 | 0.045 (4) | 0.063 (4) | 0.042 (3) | 0.018 (3) | 0.017 (3) | 0.016 (3) |
C45 | 0.089 (6) | 0.091 (6) | 0.079 (5) | 0.041 (5) | 0.063 (5) | 0.033 (5) |
C46 | 0.033 (4) | 0.103 (7) | 0.086 (5) | 0.021 (4) | 0.032 (4) | 0.017 (5) |
C47 | 0.027 (3) | 0.066 (5) | 0.057 (4) | 0.013 (3) | 0.009 (3) | 0.015 (3) |
C48 | 0.036 (3) | 0.032 (3) | 0.046 (3) | 0.016 (2) | 0.018 (2) | 0.018 (2) |
Ba1—O8 | 2.676 (4) | C7—H7A | 0.9700 |
Ba1—O11 | 2.725 (4) | C7—H7B | 0.9700 |
Ba1—O7 | 2.836 (4) | C8—H8A | 0.9700 |
Ba1—O4 | 2.886 (4) | C8—H8B | 0.9700 |
Ba1—O3 | 2.919 (4) | C9—C10 | 1.493 (8) |
Ba1—O12 | 2.930 (5) | C9—H9A | 0.9700 |
Ba1—O1 | 2.943 (3) | C9—H9B | 0.9700 |
Ba1—O2 | 2.969 (4) | C10—H10A | 0.9700 |
Ba1—O9 | 3.048 (5) | C10—H10B | 0.9700 |
Ba1—O6 | 3.048 (4) | C11—C12 | 1.510 (8) |
Ba1—O5 | 3.057 (4) | C11—H11A | 0.9700 |
Ba2—O20 | 2.710 (4) | C11—H11B | 0.9700 |
Ba2—O18 | 2.836 (4) | C12—H12A | 0.9700 |
Ba2—O16 | 2.841 (4) | C12—H12B | 0.9700 |
Ba2—O14 | 2.846 (3) | C13—C14 | 1.3900 |
Ba2—O17 | 2.868 (3) | C13—C18 | 1.3900 |
Ba2—O19 | 2.871 (4) | C14—C15 | 1.3900 |
Ba2—O25 | 2.876 (4) | C14—H14 | 0.9300 |
Ba2—O15 | 2.877 (4) | C15—C16 | 1.3900 |
Ba2—O24 | 2.890 (4) | C15—H15 | 0.9300 |
Ba2—O21 | 2.982 (5) | C16—C17 | 1.3900 |
N1—O10 | 1.230 (6) | C16—H16 | 0.9300 |
N1—O9 | 1.245 (6) | C17—C18 | 1.3900 |
N1—C24 | 1.431 (5) | C17—H17 | 0.9300 |
N2—O12 | 1.203 (7) | C19—C20 | 1.3900 |
N2—O13 | 1.211 (7) | C19—C24 | 1.3900 |
N2—C18 | 1.451 (6) | C20—C21 | 1.3900 |
N3—O22 | 1.209 (8) | C20—H20 | 0.9300 |
N3—O23 | 1.242 (7) | C21—C22 | 1.3900 |
N3—C42 | 1.427 (6) | C21—H21 | 0.9300 |
N4—O27 | 1.206 (6) | C22—C23 | 1.3900 |
N4—O28 | 1.244 (7) | C22—H22 | 0.9300 |
N4—C48 | 1.417 (6) | C23—C24 | 1.3900 |
O1—C12 | 1.416 (6) | C23—H23 | 0.9300 |
O1—C1 | 1.440 (6) | C25—C26 | 1.520 (9) |
O2—C3 | 1.433 (6) | C25—H25A | 0.9700 |
O2—C2 | 1.434 (7) | C25—H25B | 0.9700 |
O3—C5 | 1.428 (7) | C26—H26A | 0.9700 |
O3—C4 | 1.431 (7) | C26—H26B | 0.9700 |
O4—C6 | 1.435 (7) | C27—C28 | 1.483 (8) |
O4—C7 | 1.475 (7) | C27—H27A | 0.9700 |
O5—C8 | 1.425 (7) | C27—H27B | 0.9700 |
O5—C9 | 1.446 (7) | C28—H28A | 0.9700 |
O6—C11 | 1.423 (6) | C28—H28B | 0.9700 |
O6—C10 | 1.425 (6) | C29—C30 | 1.468 (8) |
O7—H1W1 | 0.9000 | C29—H29A | 0.9700 |
O7—H2W1 | 0.9001 | C29—H29B | 0.9700 |
O8—C19 | 1.358 (5) | C30—H30A | 0.9700 |
O11—C13 | 1.337 (4) | C30—H30B | 0.9700 |
O14—C25 | 1.392 (7) | C31—C32 | 1.463 (9) |
O14—C36 | 1.452 (7) | C31—H31A | 0.9700 |
O15—C26 | 1.426 (6) | C31—H31B | 0.9700 |
O15—C27 | 1.449 (7) | C32—H32A | 0.9700 |
O16—C29 | 1.420 (7) | C32—H32B | 0.9700 |
O16—C28 | 1.450 (6) | C33—C34 | 1.494 (8) |
O17—C31 | 1.437 (7) | C33—H33A | 0.9700 |
O17—C30 | 1.442 (7) | C33—H33B | 0.9700 |
O18—C32 | 1.427 (7) | C34—H34A | 0.9700 |
O18—C33 | 1.436 (7) | C34—H34B | 0.9700 |
O19—C34 | 1.413 (7) | C35—C36 | 1.476 (9) |
O19—C35 | 1.416 (7) | C35—H35A | 0.9700 |
O20—H1W2 | 0.9002 | C35—H35B | 0.9700 |
O20—H2W2 | 0.9000 | C36—H36A | 0.9700 |
O21—C37 | 1.338 (5) | C36—H36B | 0.9700 |
O24—H1W3 | 0.9001 | C37—C38 | 1.3900 |
O24—H2W3 | 0.8999 | C37—C42 | 1.3900 |
O25—H1W4 | 0.9000 | C38—C39 | 1.3900 |
O25—H2W4 | 0.9001 | C38—H38 | 0.9300 |
O26—C43 | 1.340 (4) | C39—C40 | 1.3900 |
C1—C2 | 1.495 (8) | C39—H39 | 0.9300 |
C1—H1A | 0.9700 | C40—C41 | 1.3900 |
C1—H1B | 0.9700 | C40—H40 | 0.9300 |
C2—H2A | 0.9700 | C41—C42 | 1.3900 |
C2—H2B | 0.9700 | C41—H41 | 0.9300 |
C3—C4 | 1.494 (8) | C43—C44 | 1.3900 |
C3—H3A | 0.9700 | C43—C48 | 1.3900 |
C3—H3B | 0.9700 | C44—C45 | 1.3900 |
C4—H4A | 0.9700 | C44—H44 | 0.9300 |
C4—H4B | 0.9700 | C45—C46 | 1.3900 |
C5—C6 | 1.433 (9) | C45—H45 | 0.9300 |
C5—H5A | 0.9700 | C46—C47 | 1.3900 |
C5—H5B | 0.9700 | C46—H46 | 0.9300 |
C6—H6A | 0.9700 | C47—C48 | 1.3900 |
C6—H6B | 0.9700 | C47—H47 | 0.9300 |
C7—C8 | 1.450 (9) | ||
O8—Ba1—O11 | 91.40 (13) | C6—C5—H5A | 109.5 |
O8—Ba1—O7 | 135.99 (12) | O3—C5—H5B | 109.5 |
O11—Ba1—O7 | 132.56 (12) | C6—C5—H5B | 109.5 |
O8—Ba1—O4 | 76.35 (12) | H5A—C5—H5B | 108.1 |
O11—Ba1—O4 | 122.88 (12) | C5—C6—O4 | 110.7 (5) |
O7—Ba1—O4 | 76.73 (12) | C5—C6—H6A | 109.5 |
O8—Ba1—O3 | 75.05 (12) | O4—C6—H6A | 109.5 |
O11—Ba1—O3 | 166.02 (12) | C5—C6—H6B | 109.5 |
O7—Ba1—O3 | 61.19 (12) | O4—C6—H6B | 109.5 |
O4—Ba1—O3 | 57.86 (11) | H6A—C6—H6B | 108.1 |
O8—Ba1—O12 | 71.77 (13) | C8—C7—O4 | 110.8 (5) |
O11—Ba1—O12 | 56.46 (12) | C8—C7—H7A | 109.5 |
O7—Ba1—O12 | 126.08 (13) | O4—C7—H7A | 109.5 |
O4—Ba1—O12 | 66.81 (11) | C8—C7—H7B | 109.5 |
O3—Ba1—O12 | 120.28 (11) | O4—C7—H7B | 109.5 |
O8—Ba1—O1 | 127.92 (11) | H7A—C7—H7B | 108.1 |
O11—Ba1—O1 | 83.78 (11) | O5—C8—C7 | 110.3 (5) |
O7—Ba1—O1 | 69.41 (12) | O5—C8—H8A | 109.6 |
O4—Ba1—O1 | 146.04 (11) | C7—C8—H8A | 109.6 |
O3—Ba1—O1 | 101.72 (10) | O5—C8—H8B | 109.6 |
O12—Ba1—O1 | 137.79 (11) | C7—C8—H8B | 109.6 |
O8—Ba1—O2 | 80.30 (12) | H8A—C8—H8B | 108.1 |
O11—Ba1—O2 | 118.68 (11) | O5—C9—C10 | 110.3 (4) |
O7—Ba1—O2 | 79.57 (11) | O5—C9—H9A | 109.6 |
O4—Ba1—O2 | 113.79 (11) | C10—C9—H9A | 109.6 |
O3—Ba1—O2 | 56.45 (10) | O5—C9—H9B | 109.6 |
O12—Ba1—O2 | 151.16 (12) | C10—C9—H9B | 109.6 |
O1—Ba1—O2 | 58.12 (10) | H9A—C9—H9B | 108.1 |
O8—Ba1—O9 | 55.42 (11) | O6—C10—C9 | 107.5 (4) |
O11—Ba1—O9 | 66.41 (11) | O6—C10—H10A | 110.2 |
O7—Ba1—O9 | 135.96 (12) | C9—C10—H10A | 110.2 |
O4—Ba1—O9 | 131.66 (11) | O6—C10—H10B | 110.2 |
O3—Ba1—O9 | 102.22 (11) | C9—C10—H10B | 110.2 |
O12—Ba1—O9 | 97.82 (12) | H10A—C10—H10B | 108.5 |
O1—Ba1—O9 | 75.69 (11) | O6—C11—C12 | 108.1 (4) |
O2—Ba1—O9 | 59.16 (11) | O6—C11—H11A | 110.1 |
O8—Ba1—O6 | 165.08 (12) | C12—C11—H11A | 110.1 |
O11—Ba1—O6 | 74.46 (12) | O6—C11—H11B | 110.1 |
O7—Ba1—O6 | 58.14 (11) | C12—C11—H11B | 110.1 |
O4—Ba1—O6 | 107.10 (11) | H11A—C11—H11B | 108.4 |
O3—Ba1—O6 | 119.33 (11) | O1—C12—C11 | 109.4 (4) |
O12—Ba1—O6 | 95.93 (12) | O1—C12—H12A | 109.8 |
O1—Ba1—O6 | 56.40 (10) | C11—C12—H12A | 109.8 |
O2—Ba1—O6 | 110.42 (10) | O1—C12—H12B | 109.8 |
O9—Ba1—O6 | 120.31 (10) | C11—C12—H12B | 109.8 |
O8—Ba1—O5 | 121.75 (11) | H12A—C12—H12B | 108.2 |
O11—Ba1—O5 | 86.61 (11) | O11—C13—C14 | 116.1 (3) |
O7—Ba1—O5 | 68.04 (11) | O11—C13—C18 | 123.8 (3) |
O4—Ba1—O5 | 57.42 (11) | C14—C13—C18 | 120.0 |
O3—Ba1—O5 | 103.29 (10) | C13—C14—C15 | 120.0 |
O12—Ba1—O5 | 59.17 (11) | C13—C14—H14 | 120.0 |
O1—Ba1—O5 | 109.72 (10) | C15—C14—H14 | 120.0 |
O2—Ba1—O5 | 147.53 (10) | C16—C15—C14 | 120.0 |
O9—Ba1—O5 | 152.08 (10) | C16—C15—H15 | 120.0 |
O6—Ba1—O5 | 53.96 (10) | C14—C15—H15 | 120.0 |
O20—Ba2—O18 | 84.63 (12) | C15—C16—C17 | 120.0 |
O20—Ba2—O16 | 80.60 (12) | C15—C16—H16 | 120.0 |
O18—Ba2—O16 | 118.35 (10) | C17—C16—H16 | 120.0 |
O20—Ba2—O14 | 75.42 (12) | C18—C17—C16 | 120.0 |
O18—Ba2—O14 | 116.35 (11) | C18—C17—H17 | 120.0 |
O16—Ba2—O14 | 116.83 (11) | C16—C17—H17 | 120.0 |
O20—Ba2—O17 | 74.96 (12) | C17—C18—C13 | 120.0 |
O18—Ba2—O17 | 59.39 (11) | C17—C18—N2 | 116.8 (3) |
O16—Ba2—O17 | 58.96 (11) | C13—C18—N2 | 122.8 (3) |
O14—Ba2—O17 | 150.35 (11) | O8—C19—C20 | 116.0 (3) |
O20—Ba2—O19 | 73.06 (13) | O8—C19—C24 | 124.0 (3) |
O18—Ba2—O19 | 57.77 (11) | C20—C19—C24 | 120.0 |
O16—Ba2—O19 | 153.57 (11) | C19—C20—C21 | 120.0 |
O14—Ba2—O19 | 58.64 (11) | C19—C20—H20 | 120.0 |
O17—Ba2—O19 | 110.64 (11) | C21—C20—H20 | 120.0 |
O20—Ba2—O25 | 140.80 (12) | C20—C21—C22 | 120.0 |
O18—Ba2—O25 | 129.64 (11) | C20—C21—H21 | 120.0 |
O16—Ba2—O25 | 94.82 (11) | C22—C21—H21 | 120.0 |
O14—Ba2—O25 | 72.16 (11) | C23—C22—C21 | 120.0 |
O17—Ba2—O25 | 135.16 (11) | C23—C22—H22 | 120.0 |
O19—Ba2—O25 | 106.84 (11) | C21—C22—H22 | 120.0 |
O20—Ba2—O15 | 71.43 (12) | C24—C23—C22 | 120.0 |
O18—Ba2—O15 | 156.06 (11) | C24—C23—H23 | 120.0 |
O16—Ba2—O15 | 58.14 (10) | C22—C23—H23 | 120.0 |
O14—Ba2—O15 | 58.93 (11) | C23—C24—C19 | 120.0 |
O17—Ba2—O15 | 111.72 (10) | C23—C24—N1 | 116.1 (3) |
O19—Ba2—O15 | 113.44 (11) | C19—C24—N1 | 123.9 (3) |
O25—Ba2—O15 | 73.22 (10) | O14—C25—C26 | 110.1 (5) |
O20—Ba2—O24 | 139.13 (12) | O14—C25—H25A | 109.6 |
O18—Ba2—O24 | 87.15 (11) | C26—C25—H25A | 109.6 |
O16—Ba2—O24 | 68.49 (10) | O14—C25—H25B | 109.6 |
O14—Ba2—O24 | 142.31 (11) | C26—C25—H25B | 109.6 |
O17—Ba2—O24 | 66.49 (10) | H25A—C25—H25B | 108.2 |
O19—Ba2—O24 | 132.84 (11) | O15—C26—C25 | 107.9 (5) |
O25—Ba2—O24 | 70.19 (10) | O15—C26—H26A | 110.1 |
O15—Ba2—O24 | 110.40 (11) | C25—C26—H26A | 110.1 |
O20—Ba2—O21 | 155.03 (14) | O15—C26—H26B | 110.1 |
O18—Ba2—O21 | 75.54 (12) | C25—C26—H26B | 110.1 |
O16—Ba2—O21 | 122.14 (13) | H26A—C26—H26B | 108.4 |
O14—Ba2—O21 | 99.77 (12) | O15—C27—C28 | 108.5 (4) |
O17—Ba2—O21 | 106.55 (12) | O15—C27—H27A | 110.0 |
O19—Ba2—O21 | 83.47 (13) | C28—C27—H27A | 110.0 |
O25—Ba2—O21 | 54.37 (11) | O15—C27—H27B | 110.0 |
O15—Ba2—O21 | 127.58 (11) | C28—C27—H27B | 110.0 |
O24—Ba2—O21 | 55.81 (12) | H27A—C27—H27B | 108.4 |
O10—N1—O9 | 121.1 (5) | O16—C28—C27 | 109.8 (4) |
O10—N1—C24 | 118.9 (5) | O16—C28—H28A | 109.7 |
O9—N1—C24 | 120.0 (4) | C27—C28—H28A | 109.7 |
O12—N2—O13 | 121.8 (6) | O16—C28—H28B | 109.7 |
O12—N2—C18 | 120.9 (5) | C27—C28—H28B | 109.7 |
O13—N2—C18 | 117.3 (6) | H28A—C28—H28B | 108.2 |
O22—N3—O23 | 120.7 (7) | O16—C29—C30 | 109.9 (4) |
O22—N3—C42 | 120.5 (5) | O16—C29—H29A | 109.7 |
O23—N3—C42 | 118.8 (6) | C30—C29—H29A | 109.7 |
O27—N4—O28 | 120.4 (5) | O16—C29—H29B | 109.7 |
O27—N4—C48 | 121.0 (5) | C30—C29—H29B | 109.7 |
O28—N4—C48 | 118.6 (5) | H29A—C29—H29B | 108.2 |
C12—O1—C1 | 109.0 (4) | O17—C30—C29 | 108.8 (5) |
C12—O1—Ba1 | 120.4 (3) | O17—C30—H30A | 109.9 |
C1—O1—Ba1 | 118.9 (3) | C29—C30—H30A | 109.9 |
C3—O2—C2 | 113.0 (4) | O17—C30—H30B | 109.9 |
C3—O2—Ba1 | 114.9 (3) | C29—C30—H30B | 109.9 |
C2—O2—Ba1 | 113.1 (3) | H30A—C30—H30B | 108.3 |
C5—O3—C4 | 113.9 (4) | O17—C31—C32 | 108.6 (5) |
C5—O3—Ba1 | 115.8 (3) | O17—C31—H31A | 110.0 |
C4—O3—Ba1 | 119.9 (3) | C32—C31—H31A | 110.0 |
C6—O4—C7 | 114.8 (4) | O17—C31—H31B | 110.0 |
C6—O4—Ba1 | 116.1 (3) | C32—C31—H31B | 110.0 |
C7—O4—Ba1 | 116.1 (3) | H31A—C31—H31B | 108.4 |
C8—O5—C9 | 111.7 (4) | O18—C32—C31 | 110.4 (5) |
C8—O5—Ba1 | 114.4 (3) | O18—C32—H32A | 109.6 |
C9—O5—Ba1 | 121.0 (3) | C31—C32—H32A | 109.6 |
C11—O6—C10 | 113.2 (4) | O18—C32—H32B | 109.6 |
C11—O6—Ba1 | 109.1 (3) | C31—C32—H32B | 109.6 |
C10—O6—Ba1 | 116.6 (3) | H32A—C32—H32B | 108.1 |
Ba1—O7—H1W1 | 120.3 | O18—C33—C34 | 109.9 (5) |
Ba1—O7—H2W1 | 119.7 | O18—C33—H33A | 109.7 |
H1W1—O7—H2W1 | 120.0 | C34—C33—H33A | 109.7 |
C19—O8—Ba1 | 130.5 (3) | O18—C33—H33B | 109.7 |
N1—O9—Ba1 | 132.7 (3) | C34—C33—H33B | 109.7 |
C13—O11—Ba1 | 132.3 (3) | H33A—C33—H33B | 108.2 |
N2—O12—Ba1 | 131.9 (4) | O19—C34—C33 | 109.0 (5) |
C25—O14—C36 | 110.7 (4) | O19—C34—H34A | 109.9 |
C25—O14—Ba2 | 118.5 (3) | C33—C34—H34A | 109.9 |
C36—O14—Ba2 | 116.4 (3) | O19—C34—H34B | 109.9 |
C26—O15—C27 | 112.4 (4) | C33—C34—H34B | 109.9 |
C26—O15—Ba2 | 111.6 (3) | H34A—C34—H34B | 108.3 |
C27—O15—Ba2 | 111.8 (3) | O19—C35—C36 | 108.1 (5) |
C29—O16—C28 | 112.2 (4) | O19—C35—H35A | 110.1 |
C29—O16—Ba2 | 117.6 (3) | C36—C35—H35A | 110.1 |
C28—O16—Ba2 | 120.5 (3) | O19—C35—H35B | 110.1 |
C31—O17—C30 | 112.7 (4) | C36—C35—H35B | 110.1 |
C31—O17—Ba2 | 109.0 (3) | H35A—C35—H35B | 108.4 |
C30—O17—Ba2 | 112.5 (3) | O14—C36—C35 | 109.4 (5) |
C32—O18—C33 | 111.1 (4) | O14—C36—H36A | 109.8 |
C32—O18—Ba2 | 117.1 (3) | C35—C36—H36A | 109.8 |
C33—O18—Ba2 | 120.6 (3) | O14—C36—H36B | 109.8 |
C34—O19—C35 | 113.6 (4) | C35—C36—H36B | 109.8 |
C34—O19—Ba2 | 115.6 (3) | H36A—C36—H36B | 108.2 |
C35—O19—Ba2 | 115.2 (3) | O21—C37—C38 | 118.3 (3) |
Ba2—O20—H1W2 | 120.0 | O21—C37—C42 | 121.6 (3) |
Ba2—O20—H2W2 | 120.0 | C38—C37—C42 | 120.0 |
H1W2—O20—H2W2 | 120.0 | C37—C38—C39 | 120.0 |
C37—O21—Ba2 | 131.7 (4) | C37—C38—H38 | 120.0 |
Ba2—O24—H1W3 | 120.0 | C39—C38—H38 | 120.0 |
Ba2—O24—H2W3 | 120.0 | C40—C39—C38 | 120.0 |
H1W3—O24—H2W3 | 120.0 | C40—C39—H39 | 120.0 |
Ba2—O25—H1W4 | 120.0 | C38—C39—H39 | 120.0 |
Ba2—O25—H2W4 | 120.0 | C41—C40—C39 | 120.0 |
H1W4—O25—H2W4 | 120.0 | C41—C40—H40 | 120.0 |
O1—C1—C2 | 108.2 (5) | C39—C40—H40 | 120.0 |
O1—C1—H1A | 110.1 | C42—C41—C40 | 120.0 |
C2—C1—H1A | 110.1 | C42—C41—H41 | 120.0 |
O1—C1—H1B | 110.1 | C40—C41—H41 | 120.0 |
C2—C1—H1B | 110.1 | C41—C42—C37 | 120.0 |
H1A—C1—H1B | 108.4 | C41—C42—N3 | 116.6 (3) |
O2—C2—C1 | 114.0 (5) | C37—C42—N3 | 123.4 (3) |
O2—C2—H2A | 108.8 | O26—C43—C44 | 118.1 (3) |
C1—C2—H2A | 108.8 | O26—C43—C48 | 121.9 (3) |
O2—C2—H2B | 108.8 | C44—C43—C48 | 120.0 |
C1—C2—H2B | 108.8 | C45—C44—C43 | 120.0 |
H2A—C2—H2B | 107.7 | C45—C44—H44 | 120.0 |
O2—C3—C4 | 108.8 (4) | C43—C44—H44 | 120.0 |
O2—C3—H3A | 109.9 | C44—C45—C46 | 120.0 |
C4—C3—H3A | 109.9 | C44—C45—H45 | 120.0 |
O2—C3—H3B | 109.9 | C46—C45—H45 | 120.0 |
C4—C3—H3B | 109.9 | C47—C46—C45 | 120.0 |
H3A—C3—H3B | 108.3 | C47—C46—H46 | 120.0 |
O3—C4—C3 | 107.5 (4) | C45—C46—H46 | 120.0 |
O3—C4—H4A | 110.2 | C48—C47—C46 | 120.0 |
C3—C4—H4A | 110.2 | C48—C47—H47 | 120.0 |
O3—C4—H4B | 110.2 | C46—C47—H47 | 120.0 |
C3—C4—H4B | 110.2 | C47—C48—C43 | 120.0 |
H4A—C4—H4B | 108.5 | C47—C48—N4 | 116.2 (3) |
O3—C5—C6 | 110.7 (5) | C43—C48—N4 | 123.8 (3) |
O3—C5—H5A | 109.5 | ||
O8—Ba1—O1—C12 | 165.6 (4) | O17—Ba2—O16—C29 | −9.4 (4) |
O11—Ba1—O1—C12 | 78.7 (4) | O19—Ba2—O16—C29 | 63.9 (5) |
O7—Ba1—O1—C12 | −61.4 (4) | O25—Ba2—O16—C29 | −150.7 (4) |
O4—Ba1—O1—C12 | −65.9 (4) | O15—Ba2—O16—C29 | 142.5 (4) |
O3—Ba1—O1—C12 | −114.3 (4) | O24—Ba2—O16—C29 | −84.2 (4) |
O12—Ba1—O1—C12 | 60.1 (4) | O21—Ba2—O16—C29 | −100.3 (4) |
O2—Ba1—O1—C12 | −151.8 (4) | O20—Ba2—O16—C28 | −74.7 (4) |
O9—Ba1—O1—C12 | 145.9 (4) | O18—Ba2—O16—C28 | −153.4 (3) |
O6—Ba1—O1—C12 | 3.3 (4) | O14—Ba2—O16—C28 | −6.4 (4) |
O5—Ba1—O1—C12 | −5.4 (4) | O17—Ba2—O16—C28 | −152.7 (4) |
O8—Ba1—O1—C1 | −55.3 (4) | O19—Ba2—O16—C28 | −79.4 (4) |
O11—Ba1—O1—C1 | −142.2 (4) | O25—Ba2—O16—C28 | 66.0 (4) |
O7—Ba1—O1—C1 | 77.7 (4) | O15—Ba2—O16—C28 | −0.8 (3) |
O4—Ba1—O1—C1 | 73.1 (4) | O24—Ba2—O16—C28 | 132.5 (4) |
O3—Ba1—O1—C1 | 24.8 (4) | O21—Ba2—O16—C28 | 116.4 (4) |
O12—Ba1—O1—C1 | −160.9 (4) | O20—Ba2—O17—C31 | 122.5 (4) |
O2—Ba1—O1—C1 | −12.7 (4) | O18—Ba2—O17—C31 | 29.8 (3) |
O9—Ba1—O1—C1 | −75.0 (4) | O16—Ba2—O17—C31 | −149.5 (4) |
O6—Ba1—O1—C1 | 142.4 (4) | O14—Ba2—O17—C31 | 120.0 (4) |
O5—Ba1—O1—C1 | 133.7 (4) | O19—Ba2—O17—C31 | 57.6 (4) |
O8—Ba1—O2—C3 | −99.8 (4) | O25—Ba2—O17—C31 | −87.3 (4) |
O11—Ba1—O2—C3 | 173.9 (3) | O15—Ba2—O17—C31 | −175.0 (3) |
O7—Ba1—O2—C3 | 40.8 (3) | O24—Ba2—O17—C31 | −71.4 (3) |
O4—Ba1—O2—C3 | −29.5 (4) | O21—Ba2—O17—C31 | −31.6 (4) |
O3—Ba1—O2—C3 | −21.4 (3) | O20—Ba2—O17—C30 | −111.8 (3) |
O12—Ba1—O2—C3 | −114.3 (4) | O18—Ba2—O17—C30 | 155.6 (4) |
O1—Ba1—O2—C3 | 113.0 (4) | O16—Ba2—O17—C30 | −23.8 (3) |
O9—Ba1—O2—C3 | −155.2 (4) | O14—Ba2—O17—C30 | −114.2 (4) |
O6—Ba1—O2—C3 | 90.9 (3) | O19—Ba2—O17—C30 | −176.7 (3) |
O5—Ba1—O2—C3 | 36.7 (4) | O25—Ba2—O17—C30 | 38.4 (4) |
O8—Ba1—O2—C2 | 128.3 (4) | O15—Ba2—O17—C30 | −49.3 (3) |
O11—Ba1—O2—C2 | 42.1 (4) | O24—Ba2—O17—C30 | 54.4 (3) |
O7—Ba1—O2—C2 | −91.0 (4) | O21—Ba2—O17—C30 | 94.1 (3) |
O4—Ba1—O2—C2 | −161.4 (3) | O20—Ba2—O18—C32 | −73.0 (4) |
O3—Ba1—O2—C2 | −153.2 (4) | O16—Ba2—O18—C32 | 3.3 (4) |
O12—Ba1—O2—C2 | 113.9 (4) | O14—Ba2—O18—C32 | −143.8 (4) |
O1—Ba1—O2—C2 | −18.9 (3) | O17—Ba2—O18—C32 | 2.7 (3) |
O9—Ba1—O2—C2 | 73.0 (4) | O19—Ba2—O18—C32 | −146.4 (4) |
O6—Ba1—O2—C2 | −40.9 (4) | O25—Ba2—O18—C32 | 128.1 (4) |
O5—Ba1—O2—C2 | −95.1 (4) | O15—Ba2—O18—C32 | −71.5 (5) |
O8—Ba1—O3—C5 | −68.6 (4) | O24—Ba2—O18—C32 | 66.9 (4) |
O11—Ba1—O3—C5 | −83.0 (6) | O21—Ba2—O18—C32 | 122.3 (4) |
O7—Ba1—O3—C5 | 106.6 (4) | O20—Ba2—O18—C33 | 67.5 (4) |
O4—Ba1—O3—C5 | 14.5 (4) | O16—Ba2—O18—C33 | 143.8 (4) |
O12—Ba1—O3—C5 | −10.7 (4) | O14—Ba2—O18—C33 | −3.3 (4) |
O1—Ba1—O3—C5 | 165.0 (4) | O17—Ba2—O18—C33 | 143.2 (4) |
O2—Ba1—O3—C5 | −156.7 (4) | O19—Ba2—O18—C33 | −5.8 (4) |
O9—Ba1—O3—C5 | −117.4 (4) | O25—Ba2—O18—C33 | −91.4 (4) |
O6—Ba1—O3—C5 | 107.1 (4) | O15—Ba2—O18—C33 | 69.0 (5) |
O5—Ba1—O3—C5 | 51.2 (4) | O24—Ba2—O18—C33 | −152.6 (4) |
O8—Ba1—O3—C4 | 74.5 (4) | O21—Ba2—O18—C33 | −97.2 (4) |
O11—Ba1—O3—C4 | 60.0 (6) | O20—Ba2—O19—C34 | −120.2 (4) |
O7—Ba1—O3—C4 | −110.4 (4) | O18—Ba2—O19—C34 | −25.8 (3) |
O4—Ba1—O3—C4 | 157.5 (4) | O16—Ba2—O19—C34 | −115.4 (4) |
O12—Ba1—O3—C4 | 132.4 (4) | O14—Ba2—O19—C34 | 156.8 (4) |
O1—Ba1—O3—C4 | −52.0 (4) | O17—Ba2—O19—C34 | −54.1 (4) |
O2—Ba1—O3—C4 | −13.7 (4) | O25—Ba2—O19—C34 | 100.8 (4) |
O9—Ba1—O3—C4 | 25.7 (4) | O15—Ba2—O19—C34 | 179.4 (3) |
O6—Ba1—O3—C4 | −109.9 (4) | O24—Ba2—O19—C34 | 22.5 (4) |
O5—Ba1—O3—C4 | −165.8 (4) | O21—Ba2—O19—C34 | 51.2 (4) |
O8—Ba1—O4—C6 | 98.0 (4) | O20—Ba2—O19—C35 | 104.1 (4) |
O11—Ba1—O4—C6 | −179.3 (4) | O18—Ba2—O19—C35 | −161.6 (4) |
O7—Ba1—O4—C6 | −46.8 (4) | O16—Ba2—O19—C35 | 108.9 (4) |
O3—Ba1—O4—C6 | 17.3 (4) | O14—Ba2—O19—C35 | 21.1 (3) |
O12—Ba1—O4—C6 | 173.8 (4) | O17—Ba2—O19—C35 | 170.2 (3) |
O1—Ba1—O4—C6 | −42.5 (5) | O25—Ba2—O19—C35 | −34.9 (4) |
O2—Ba1—O4—C6 | 25.3 (4) | O15—Ba2—O19—C35 | 43.7 (4) |
O9—Ba1—O4—C6 | 94.3 (4) | O24—Ba2—O19—C35 | −113.2 (4) |
O6—Ba1—O4—C6 | −97.0 (4) | O21—Ba2—O19—C35 | −84.6 (4) |
O5—Ba1—O4—C6 | −119.1 (4) | O20—Ba2—O21—C37 | 10.0 (6) |
O8—Ba1—O4—C7 | −122.4 (4) | O18—Ba2—O21—C37 | 48.5 (4) |
O11—Ba1—O4—C7 | −39.7 (4) | O16—Ba2—O21—C37 | 163.2 (4) |
O7—Ba1—O4—C7 | 92.7 (4) | O14—Ba2—O21—C37 | −66.4 (4) |
O3—Ba1—O4—C7 | 156.8 (4) | O17—Ba2—O21—C37 | 99.8 (4) |
O12—Ba1—O4—C7 | −46.7 (4) | O19—Ba2—O21—C37 | −9.8 (4) |
O1—Ba1—O4—C7 | 97.1 (4) | O25—Ba2—O21—C37 | −126.0 (5) |
O2—Ba1—O4—C7 | 164.8 (4) | O15—Ba2—O21—C37 | −124.5 (4) |
O9—Ba1—O4—C7 | −126.1 (4) | O24—Ba2—O21—C37 | 145.0 (5) |
O6—Ba1—O4—C7 | 42.5 (4) | C12—O1—C1—C2 | −175.8 (5) |
O5—Ba1—O4—C7 | 20.5 (4) | Ba1—O1—C1—C2 | 40.9 (6) |
O8—Ba1—O5—C8 | 55.4 (4) | C3—O2—C2—C1 | −82.5 (6) |
O11—Ba1—O5—C8 | 145.0 (4) | Ba1—O2—C2—C1 | 50.3 (6) |
O7—Ba1—O5—C8 | −76.1 (4) | O1—C1—C2—O2 | −61.2 (7) |
O4—Ba1—O5—C8 | 11.9 (4) | C2—O2—C3—C4 | −174.7 (5) |
O3—Ba1—O5—C8 | −25.1 (4) | Ba1—O2—C3—C4 | 53.4 (5) |
O12—Ba1—O5—C8 | 92.5 (4) | C5—O3—C4—C3 | −171.3 (5) |
O1—Ba1—O5—C8 | −132.9 (4) | Ba1—O3—C4—C3 | 45.0 (6) |
O2—Ba1—O5—C8 | −71.7 (4) | O2—C3—C4—O3 | −63.8 (6) |
O9—Ba1—O5—C8 | 130.5 (4) | C4—O3—C5—C6 | 169.5 (5) |
O6—Ba1—O5—C8 | −141.8 (4) | Ba1—O3—C5—C6 | −45.3 (6) |
O8—Ba1—O5—C9 | −166.3 (4) | O3—C5—C6—O4 | 62.1 (7) |
O11—Ba1—O5—C9 | −76.7 (4) | C7—O4—C6—C5 | 171.6 (5) |
O7—Ba1—O5—C9 | 62.2 (4) | Ba1—O4—C6—C5 | −48.3 (6) |
O4—Ba1—O5—C9 | 150.2 (4) | C6—O4—C7—C8 | 86.8 (6) |
O3—Ba1—O5—C9 | 113.3 (4) | Ba1—O4—C7—C8 | −53.2 (6) |
O12—Ba1—O5—C9 | −129.2 (4) | C9—O5—C8—C7 | 174.8 (5) |
O1—Ba1—O5—C9 | 5.4 (4) | Ba1—O5—C8—C7 | −43.0 (6) |
O2—Ba1—O5—C9 | 66.6 (4) | O4—C7—C8—O5 | 64.1 (7) |
O9—Ba1—O5—C9 | −91.2 (4) | C8—O5—C9—C10 | 172.7 (5) |
O6—Ba1—O5—C9 | −3.5 (4) | Ba1—O5—C9—C10 | 33.4 (6) |
O8—Ba1—O6—C11 | −81.1 (5) | C11—O6—C10—C9 | −172.9 (5) |
O11—Ba1—O6—C11 | −62.1 (3) | Ba1—O6—C10—C9 | 59.3 (5) |
O7—Ba1—O6—C11 | 115.9 (4) | O5—C9—C10—O6 | −59.2 (6) |
O4—Ba1—O6—C11 | 177.6 (3) | C10—O6—C11—C12 | 165.9 (5) |
O3—Ba1—O6—C11 | 115.4 (3) | Ba1—O6—C11—C12 | −62.5 (5) |
O12—Ba1—O6—C11 | −114.9 (3) | C1—O1—C12—C11 | −177.6 (5) |
O1—Ba1—O6—C11 | 30.7 (3) | Ba1—O1—C12—C11 | −35.0 (6) |
O2—Ba1—O6—C11 | 53.2 (3) | O6—C11—C12—O1 | 66.2 (6) |
O9—Ba1—O6—C11 | −12.2 (4) | Ba1—O11—C13—C14 | 135.5 (3) |
O5—Ba1—O6—C11 | −159.4 (4) | Ba1—O11—C13—C18 | −40.6 (5) |
O8—Ba1—O6—C10 | 48.7 (6) | O11—C13—C14—C15 | −176.3 (4) |
O11—Ba1—O6—C10 | 67.7 (3) | C13—C14—C15—C16 | 0.0 |
O7—Ba1—O6—C10 | −114.3 (4) | C14—C15—C16—C17 | 0.0 |
O4—Ba1—O6—C10 | −52.6 (3) | C15—C16—C17—C18 | 0.0 |
O3—Ba1—O6—C10 | −114.8 (3) | C16—C17—C18—C13 | 0.0 |
O12—Ba1—O6—C10 | 15.0 (3) | C16—C17—C18—N2 | −173.4 (4) |
O1—Ba1—O6—C10 | 160.6 (4) | O11—C13—C18—C17 | 176.0 (4) |
O2—Ba1—O6—C10 | −177.0 (3) | C14—C13—C18—C17 | 0.0 |
O9—Ba1—O6—C10 | 117.6 (3) | O11—C13—C18—N2 | −11.0 (5) |
O5—Ba1—O6—C10 | −29.6 (3) | C14—C13—C18—N2 | 173.0 (4) |
O11—Ba1—O8—C19 | 118.6 (4) | O12—N2—C18—C17 | −177.7 (4) |
O7—Ba1—O8—C19 | −64.1 (4) | O13—N2—C18—C17 | 0.5 (7) |
O4—Ba1—O8—C19 | −117.9 (4) | O12—N2—C18—C13 | 9.0 (7) |
O3—Ba1—O8—C19 | −58.0 (4) | O13—N2—C18—C13 | −172.7 (6) |
O12—Ba1—O8—C19 | 172.4 (4) | Ba1—O8—C19—C20 | 123.0 (3) |
O1—Ba1—O8—C19 | 35.4 (4) | Ba1—O8—C19—C24 | −58.7 (5) |
O2—Ba1—O8—C19 | −0.3 (4) | O8—C19—C20—C21 | 178.4 (4) |
O9—Ba1—O8—C19 | 58.8 (4) | C24—C19—C20—C21 | 0.0 |
O6—Ba1—O8—C19 | 136.8 (4) | C19—C20—C21—C22 | 0.0 |
O5—Ba1—O8—C19 | −154.6 (3) | C20—C21—C22—C23 | 0.0 |
O10—N1—O9—Ba1 | −148.7 (4) | C21—C22—C23—C24 | 0.0 |
C24—N1—O9—Ba1 | 31.3 (7) | C22—C23—C24—C19 | 0.0 |
O8—Ba1—O9—N1 | −49.1 (4) | C22—C23—C24—N1 | 179.4 (4) |
O11—Ba1—O9—N1 | −158.6 (5) | O8—C19—C24—C23 | −178.2 (4) |
O7—Ba1—O9—N1 | 73.8 (5) | C20—C19—C24—C23 | 0.0 |
O4—Ba1—O9—N1 | −44.7 (5) | O8—C19—C24—N1 | 2.5 (5) |
O3—Ba1—O9—N1 | 12.9 (5) | C20—C19—C24—N1 | −179.3 (4) |
O12—Ba1—O9—N1 | −110.5 (4) | O10—N1—C24—C23 | 7.4 (6) |
O1—Ba1—O9—N1 | 112.1 (5) | O9—N1—C24—C23 | −172.7 (4) |
O2—Ba1—O9—N1 | 50.9 (4) | O10—N1—C24—C19 | −173.2 (4) |
O6—Ba1—O9—N1 | 147.9 (4) | O9—N1—C24—C19 | 6.7 (6) |
O5—Ba1—O9—N1 | −142.7 (4) | C36—O14—C25—C26 | 175.8 (5) |
O8—Ba1—O11—C13 | 119.2 (4) | Ba2—O14—C25—C26 | 37.5 (6) |
O7—Ba1—O11—C13 | −58.3 (4) | C27—O15—C26—C25 | −175.9 (5) |
O4—Ba1—O11—C13 | 44.6 (4) | Ba2—O15—C26—C25 | 57.6 (5) |
O3—Ba1—O11—C13 | 133.1 (5) | O14—C25—C26—O15 | −63.9 (7) |
O12—Ba1—O11—C13 | 52.2 (4) | C26—O15—C27—C28 | 172.9 (5) |
O1—Ba1—O11—C13 | −112.8 (4) | Ba2—O15—C27—C28 | −60.7 (5) |
O2—Ba1—O11—C13 | −161.1 (4) | C29—O16—C28—C27 | −173.8 (5) |
O9—Ba1—O11—C13 | 170.1 (4) | Ba2—O16—C28—C27 | −28.7 (6) |
O6—Ba1—O11—C13 | −56.0 (4) | O15—C27—C28—O16 | 58.6 (6) |
O5—Ba1—O11—C13 | −2.5 (4) | C28—O16—C29—C30 | −172.7 (5) |
O13—N2—O12—Ba1 | −137.8 (6) | Ba2—O16—C29—C30 | 41.1 (6) |
C18—N2—O12—Ba1 | 40.4 (8) | C31—O17—C30—C29 | 178.9 (4) |
O8—Ba1—O12—N2 | −159.3 (5) | Ba2—O17—C30—C29 | 55.2 (5) |
O11—Ba1—O12—N2 | −54.9 (5) | O16—C29—C30—O17 | −64.2 (6) |
O7—Ba1—O12—N2 | 66.5 (5) | C30—O17—C31—C32 | 172.6 (5) |
O4—Ba1—O12—N2 | 118.1 (5) | Ba2—O17—C31—C32 | −61.7 (5) |
O3—Ba1—O12—N2 | 141.1 (5) | C33—O18—C32—C31 | −178.8 (5) |
O1—Ba1—O12—N2 | −32.5 (6) | Ba2—O18—C32—C31 | −34.7 (6) |
O2—Ba1—O12—N2 | −144.3 (5) | O17—C31—C32—O18 | 65.7 (6) |
O9—Ba1—O12—N2 | −109.8 (5) | C32—O18—C33—C34 | 176.8 (5) |
O6—Ba1—O12—N2 | 12.0 (5) | Ba2—O18—C33—C34 | 34.2 (6) |
O5—Ba1—O12—N2 | 53.3 (5) | C35—O19—C34—C33 | −169.6 (5) |
O20—Ba2—O14—C25 | 70.4 (4) | Ba2—O19—C34—C33 | 54.0 (5) |
O18—Ba2—O14—C25 | 146.7 (4) | O18—C33—C34—O19 | −56.8 (6) |
O16—Ba2—O14—C25 | −0.9 (4) | C34—O19—C35—C36 | 170.9 (5) |
O17—Ba2—O14—C25 | 72.8 (5) | Ba2—O19—C35—C36 | −52.5 (6) |
O19—Ba2—O14—C25 | 149.2 (4) | C25—O14—C36—C35 | 175.8 (5) |
O25—Ba2—O14—C25 | −87.3 (4) | Ba2—O14—C36—C35 | −45.1 (6) |
O15—Ba2—O14—C25 | −6.5 (4) | O19—C35—C36—O14 | 64.2 (6) |
O24—Ba2—O14—C25 | −89.9 (4) | Ba2—O21—C37—C38 | 94.1 (4) |
O21—Ba2—O14—C25 | −134.7 (4) | Ba2—O21—C37—C42 | −82.6 (5) |
O20—Ba2—O14—C36 | −65.6 (4) | O21—C37—C38—C39 | −176.8 (5) |
O18—Ba2—O14—C36 | 10.7 (4) | C42—C37—C38—C39 | 0.0 |
O16—Ba2—O14—C36 | −136.9 (4) | C37—C38—C39—C40 | 0.0 |
O17—Ba2—O14—C36 | −63.1 (4) | C38—C39—C40—C41 | 0.0 |
O19—Ba2—O14—C36 | 13.2 (4) | C39—C40—C41—C42 | 0.0 |
O25—Ba2—O14—C36 | 136.8 (4) | C40—C41—C42—C37 | 0.0 |
O15—Ba2—O14—C36 | −142.4 (4) | C40—C41—C42—N3 | −179.6 (4) |
O24—Ba2—O14—C36 | 134.1 (4) | O21—C37—C42—C41 | 176.6 (5) |
O21—Ba2—O14—C36 | 89.3 (4) | C38—C37—C42—C41 | 0.0 |
O20—Ba2—O15—C26 | −111.4 (4) | O21—C37—C42—N3 | −3.8 (6) |
O18—Ba2—O15—C26 | −112.9 (4) | C38—C37—C42—N3 | 179.6 (4) |
O16—Ba2—O15—C26 | 158.3 (4) | O22—N3—C42—C41 | 147.1 (5) |
O14—Ba2—O15—C26 | −27.5 (3) | O23—N3—C42—C41 | −31.0 (6) |
O17—Ba2—O15—C26 | −176.0 (3) | O22—N3—C42—C37 | −32.5 (7) |
O19—Ba2—O15—C26 | −50.1 (4) | O23—N3—C42—C37 | 149.4 (4) |
O25—Ba2—O15—C26 | 51.4 (4) | O26—C43—C44—C45 | 178.4 (4) |
O24—Ba2—O15—C26 | 112.1 (4) | C48—C43—C44—C45 | 0.0 |
O21—Ba2—O15—C26 | 50.1 (4) | C43—C44—C45—C46 | 0.0 |
O20—Ba2—O15—C27 | 121.8 (4) | C44—C45—C46—C47 | 0.0 |
O18—Ba2—O15—C27 | 120.2 (4) | C45—C46—C47—C48 | 0.0 |
O16—Ba2—O15—C27 | 31.5 (3) | C46—C47—C48—C43 | 0.0 |
O14—Ba2—O15—C27 | −154.4 (4) | C46—C47—C48—N4 | 178.8 (4) |
O17—Ba2—O15—C27 | 57.2 (4) | O26—C43—C48—C47 | −178.4 (4) |
O19—Ba2—O15—C27 | −176.9 (3) | C44—C43—C48—C47 | 0.0 |
O25—Ba2—O15—C27 | −75.4 (3) | O26—C43—C48—N4 | 2.9 (5) |
O24—Ba2—O15—C27 | −14.7 (4) | C44—C43—C48—N4 | −178.7 (4) |
O21—Ba2—O15—C27 | −76.7 (4) | O27—N4—C48—C47 | −155.0 (5) |
O20—Ba2—O16—C29 | 68.6 (4) | O28—N4—C48—C47 | 27.5 (6) |
O18—Ba2—O16—C29 | −10.0 (4) | O27—N4—C48—C43 | 23.8 (7) |
O14—Ba2—O16—C29 | 136.9 (4) | O28—N4—C48—C43 | −153.7 (5) |
Experimental details
Crystal data | |
Chemical formula | [Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)] |
Mr | 1427.78 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 13.7492 (3), 14.9672 (3), 16.8669 (3) |
α, β, γ (°) | 97.9362 (2), 109.7546 (7), 108.8642 (7) |
V (Å3) | 2969.6 (1) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.41 |
Crystal size (mm) | 0.24 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.729, 0.766 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17916, 13455, 10337 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.171, 0.96 |
No. of reflections | 13455 |
No. of parameters | 692 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.47, −2.90 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
O2—C2 | 1.434 (7) | C1—C2 | 1.495 (8) |
O1—C1—C2 | 108.2 (5) | O2—C2—C1 | 114.0 (5) |
O1—C1—C2—O2 | −61.2 (7) |
D-H···A | D-H | H···A | D···A | D-H···A |
O7-H21W···O26ii | 0.90 | 2.04 | 2.838 (7) | 147 |
O20-H12W···O11i | 0.90 | 2.23 | 2.953 (6) | 138 |
O20-H12W···O12i | 0.90 | 2.38 | 2.998 (6) | 126 |
O20-H22W···O8i | 0.90 | 2.09 | 2.880 (7) | 146 |
O25-H24W···O27i | 0.90 | 2.27 | 3.012 (7) | 139 |
C3-H3A···O26ii | 0.97 | 2.59 | 3.485 (7) | 154 |
C36-H36A···O27iii | 0.97 | 2.50 | 3.296 (10) | 139 |
Symmetry codes: (i) x, y, z; (ii) x, y-1, z; (iii) -x, 1-y, 1-z |
Several complexes of barium with 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) have been reported (Wei et al., 1988; Rheingold et al., 1993; Usman et al., 2002). In these papers, analyses of the structures of the complexes and the temperature-dependent crystal cell parameters were the main interest. As part of our systematic studies of the temperature-dependent crystal cell parameters of 18-crown-6 complexed with barium(II) phenolate derivatives, we have prepared the title ternary complex, (I). However, the cell parameters are almost constant in the temperature range from 300 K to 183 K. An X-ray crystal structure determination of (I) was undertaken at 300 K, and the result is reported here. Compound (I) is a ternary complex of neutral aqua-18-crown-6-barium(II)bis(o-nitrophenolate), a triaqua-18-crown-6-barium(II)-o-nitrophenolate cation, and an o-nitrophenolate anion. \sch
In the neutral moiety, the Ba2+ cation is eleven-coordinate, which is rare for Ba in 18-crown-6-barium(II) complexes, to the six O atoms of the crown (average Ba—Ocrown 2.970 Å), to the water O atom on one side [Ba—Owater 2.836 (4) Å] and to the O atoms of the phenolate and nitro groups of two o-nitrophenolates on the opposite side (average Ba—Ophenolate 2.700 Å and Ba—Onitro 2.989 Å). These average B—O bond lengths are slightly elongated when compared with those in related structures [Ba—Ocrown 2.823 Å (Rheingold et al.,1993) and 2.794 Å (Usman et al., 2002), and Ba—Ophenolate 2.689 Å and Ba—Onitro 2.995 Å (Usman et al., 2002)].
The rigid 18-crown-6, as is usually observed, has approximately D3 d symmetry, with average C—O and C—C bond distances of 1.434 and 1.479 Å, respectively, and O—C—C—O and C—O—C—C torsion angles close to +sc or -sc and ap. The O atoms of the crown form a regular hexagon ether, with nonbonded O···O distances in the range 2.771 (5)–2.871 (5) Å, and, together with atoms Ba1 and O7, they form a distorted hexagonal bipyramid. The apices Ba1 and O7 are displaced by 1.055 (1) and 1.775 (1) Å, respectively, from the basal hexagon O ether. The aromatic rings, A and B, of the two phenolates and the crown plane make dihedral angles of 12.8 (2) and 14.9 (2)°, respectively. The nitro groups (N1/O9/O10 and N2/O12/O13) are twisted by an angle of 7.1 (3)° from their attached aromatic ring.
In the cationic moiety, the Ba2+ cation is ten-coordinate, as is usually observed in 18-crown-6-barium(II) complexes (Wei et al., 1988; Rheingold et al., 1993; Usman et al., 2002), to the six O atoms of the crown (average Ba—Ocrown 2.856 Å), to the three water O molecules (average Ba—Owater 2.825 Å) and to the phenolate O atom [Ba—Ophenolate 2.982 (5) Å]. The average Ba—Ocrown and Ba—Owater bond lengths are slightly shorter, whereas the Ba—Ophenolate bond is slightly longer, when compared with the corresponding values in the neutral moiety.
The crown ether of this moiety also adopts approximately D3 d symmetry. The average C—O and C—C bond distances [1.430 and 1.484 Å, respectively], the O—C—C and C—O—C angles [average O—C—C 109.3° and C—O—C 112.2°], and O—C—C—O and C—O—C—C torsion angles are all comparable with those in the neutral moiety. Also similar is the hexagonal bipyramid formed by the regular hexagon of the O atoms of the crown ether, with atoms Ba2 and O20 being the apices. The O···O distances of the hexagon are in the range 2.778 (5)–2.826 (6) Å, and atoms Ba2 and O20 are displaced by 0.656 and 2.056 Å, respectively. The aromatic ring C of the phenolate and the crown plane make a dihedral angle of 19.9 (2)°, and the nitro group (N3/O22/O23) is twisted by an angle of 31.7 (3)° from the aromatic ring.
In the phenolate counteranion, D, the nitro group (N4/O27/O28) is twisted by an angle of 25.8 (3)° from the aromatic ring. This ring is coplanar with aromatic ring C, the corresponding angle between these two being 0.6 (2)°. The closest atom to Ba2 is atom O26, with Ba2···O26 4.277 (5) Å.
It should be noted that both crown ring systems (neutral and cation moieties) are eclipsed and coplanar to each other, with the average Ocrown—Ba1···Ba2—Ocrown torsion angle being 1.0° and the dihedral angle between the crown ring systems being 1.7 (1)°. The crown of the neutral moiety is translated by 6.766 Å from the crown of the cation moiety, approximately along the b direction. However, the two pairs of phenolates, A and B, and C and D, have slightly different orientations towards their crown rings due to the different Ba—Onitro bonds. The twisted angles of the nitro groups of phenolates A and B are also much smaller compared with those in phenolates C and D.
In the asymmetric unit of (I), the three components are interconnected via intermolecular O20—H12W···O11, O20—H12W···O12, O20—H22W···O8 and O25—H24W···O27 interactions (Table 2). The symmetry-related neutral and cationic moieties are linked by a C3—H3A···O26i intermolecular bond into molecular columns along the b direction, and these molecular columns are interconnected by C36—H36A···O27ii and O7—H21W···O26ii interactions (Fig. 2) [symmetry codes: (i) x, y - 1, z; (ii) 2 - x, 1 - y, 1 - z].