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The title compound, 1,4,8,11,14,18,23,27-octa­aza-6,16,25(2,6)- tripyridinabi­cyclo­[9.9.9]­nonacosaphane(8+) octaperchlorate pen­ta­hydrate, C33H59N118+·8ClO4-·5H2O, is a salt of an octaprotonated cryptand in which one of the pyridine groups and the bridgehead tertiary amines remain unprotonated. The central cavity of the cryptand is not occupied, although the perchlorate ions are hydrogen bonded in clefts formed between the arms of the cryptand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103002580/bm1519sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103002580/bm1519Isup2.hkl
Contains datablock I

CCDC reference: 208027

Comment top

Protonated aminocryptands have previously been shown to be versatile hosts for polyatomic oxoanions (Morgan et al., 1995; Hynes et al., 2000; Maubert et al., 2001; Farrell et al., 2003). In these examples, either one or two anions are encapsulated within the cavity of the cryptand, most commonly by a mixture of direct (anion-protonated amine) and indirect (anion–water-protonated amine) hydrogen bonding. The hexaprotonated form of the pyridine-containing cryptand L has been shown to bind a single SiF62− ion within the cavity via six (amine)NH···F hydrogen bonds, while four BF4 ions are located in the lattice but clearly outside the host.

In contrast, the octaprotonated form of the host in the title compound, (I), binds three of the perchlorate anions in sites within clefts formed between the arms [## AUTHOR - change OK? ##] of the cryptand.

Fig. 1 shows the conformation of the protonated cryptand. The six secondary amine groups are protonated, but the tertiary amines of the bridgeheads (N1 and N2) are not. Two of the pyridine groups are protonated (at N4A and N4C), and the planes of these rings are aligned tangentially to the body of the cryptand and are almost parallel to each other (Fig. 2). The hydrogen atoms attached to N4A and N4C were located from difference maps, and there is further support for this assignment in the observation of hydrogen bonding between these two pyridine groups and perchlorate O atoms.

Protonation of the pyridine rings rather than the bridgehead N atoms would be surprising if the pKa values of these groups were close to those of free pyridine and triethylamine (pKa = 5.25 and 11.01, respectively). Within the constraints the cage framework, however, this assumption appears not to hold. In part, this behaviour may be due to some flattening of the tetrahedral geometry at the bridgehead N atoms, which reflects a tendency towards sp2 hybridization and therefore a decrease in basicity. However, geometric evidence for sp2 hybridization is slight; the angle sums at N1 and N2 are 338 (8) and 337 (9)°, respectively. An alternative possibility is that, since protonation is stabilized by hydrogen bonding, the observed protonation pattern is a consequence of the hydrogen bonding in the lattice.

As with other reported anion cryptates (Morgan et al., 1995; Hynes et al., 2000; Maubert et al., 2001; Farrell et al., 2003) the hydrogen-bonding network linking cation, anions and solvate water molecules is complex. The individual hydrogen bonds are listed in Table 1, while Fig. 2 illustrates the binding of the three perchlorate anions most closely associated with the clefts between the arms of the cryptand. Each of the eight perchlorate anions forms at least one hydrogen bond to a protonated group of the cryptand, and each cryptand NH2+ ion forms at least two hydrogen bonds (some are bifurcated) to O atoms of either perchlorate or water. The solvate water molecules facilitate further hydrogen-bonding interactions that extend through the lattice.

The hexaprotonated analogue of the cryptand can selectively encapsulate SiF62− in preference to BF4 (Morgan et al., 1995). Although this observation can be partly explained on the basis of charge selectivity, taken in tandem with the present result this preference might also suggest that the cryptand does not favour tetrahedral guests. However, as it is equally possible that the octaprotonated cryptand adopts this geometry to maximize the hydrogen bonding and hence minimize the energy of the structure, the structures of other hexa- or octaprotonated cryptates of this ligand will be of much interest.

Experimental top

The neutral cryptand was prepared by the literature method (Marrs et al., 1993). It was then dissolved in ethanol and perchloric acid was added until the pH was approximately 2. Colourless crystals of the complex crystallized out of this solution over approximately two weeks.

Refinement top

H atoms bonded to C atoms or amine N atoms were inserted at calculated positions; those bonded to O atoms or to the pyridine N atoms were located from difference maps. The constrained C—H distances were 0.95, 0.99 and 0.92 Å for aryl, methylene and amine H atoms, respectively, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: XSCANS (Siemens, 1990a); cell refinement: XSCANS (Siemens, 1990a); data reduction: XSCANS (Siemens, 1990a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. A perspective view of the title cation showing 50% probability displacement ellipsoids. H atoms bonded to C atoms have been omitted for clarity.
[Figure 2] Fig. 2. A perspective diagram showing the three perchlorate anions hydrogen bonded into the clefts between strands of the protonated cryptand. Hydrogen bonds are shown as dashed lines.
[Figure 3] Fig. 3. A projection of the unit cell along a with hydrogen bonds shown as dashed lines.
(I) top
Crystal data top
C33H59N118+·8ClO4·5H2OZ = 2
Mr = 1495.59F(000) = 1552
Triclinic, P1Dx = 1.719 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.9265 (13) ÅCell parameters from 36 reflections
b = 13.6798 (14) Åθ = 4.5–12.5°
c = 18.5310 (19) ŵ = 0.50 mm1
α = 84.258 (9)°T = 128 K
β = 76.394 (8)°Block, colourless
γ = 65.092 (8)°0.82 × 0.52 × 0.36 mm
V = 2888.7 (6) Å3
Data collection top
Siemens P4
diffractometer
7315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.105
Graphite monochromatorθmax = 24.0°, θmin = 2.3°
ω scansh = 014
Absorption correction: ψ scan
(SHELXTL/PC; Siemens, 1990b)
k = 1415
Tmin = 0.862, Tmax = 0.972l = 2021
9513 measured reflections3 standard reflections every 97 reflections
9055 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.058P)2 + 4.792P]
where P = (Fo2 + 2Fc2)/3
9055 reflections(Δ/σ)max = 0.001
838 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.67 e Å3
Crystal data top
C33H59N118+·8ClO4·5H2Oγ = 65.092 (8)°
Mr = 1495.59V = 2888.7 (6) Å3
Triclinic, P1Z = 2
a = 12.9265 (13) ÅMo Kα radiation
b = 13.6798 (14) ŵ = 0.50 mm1
c = 18.5310 (19) ÅT = 128 K
α = 84.258 (9)°0.82 × 0.52 × 0.36 mm
β = 76.394 (8)°
Data collection top
Siemens P4
diffractometer
7315 reflections with I > 2σ(I)
Absorption correction: ψ scan
(SHELXTL/PC; Siemens, 1990b)
Rint = 0.105
Tmin = 0.862, Tmax = 0.972θmax = 24.0°
9513 measured reflections3 standard reflections every 97 reflections
9055 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.65 e Å3
9055 reflectionsΔρmin = 0.67 e Å3
838 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. The structure was solved by direct methods (Sheldrick, 1990), and all the non-H atoms were refined with anisotropic atomic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.2799 (2)0.5830 (2)0.19115 (14)0.0124 (6)
C1A1.3201 (3)0.6256 (3)0.11925 (18)0.0146 (7)
H1A11.37290.56500.08500.018*
H1A21.36470.66640.12620.018*
C2A1.2179 (3)0.6988 (3)0.08536 (18)0.0159 (7)
H2A11.16970.65990.08190.019*
H2A21.16840.76260.11750.019*
N3A1.2608 (2)0.7344 (2)0.00966 (14)0.0142 (6)
H3A11.30240.67490.02060.017*
H3A21.31090.76480.01290.017*
C3A1.1640 (3)0.8144 (3)0.02510 (18)0.0164 (7)
H3A31.19730.83050.07630.020*
H3A41.12600.88240.00360.020*
C4A1.0738 (3)0.7727 (3)0.02723 (17)0.0134 (7)
C5A1.0915 (3)0.6930 (3)0.07367 (19)0.0190 (8)
H5A1.16270.66270.10920.023*
C6A1.0050 (3)0.6567 (3)0.0686 (2)0.0214 (8)
H6A1.01800.59990.09990.026*
C7A0.8990 (3)0.7028 (3)0.01793 (19)0.0198 (8)
H7A0.83970.67770.01420.024*
C8A0.8819 (3)0.7851 (3)0.02657 (18)0.0143 (7)
N4A0.9700 (2)0.8158 (2)0.02143 (15)0.0143 (6)
H4A0.961 (3)0.865 (3)0.050 (2)0.017*
C9A0.7710 (3)0.8482 (3)0.08157 (19)0.0176 (7)
H9A10.79110.87290.12270.021*
H9A20.72200.91290.05670.021*
N5A0.7023 (2)0.7828 (2)0.11291 (15)0.0167 (6)
H5A10.74780.72370.13680.020*
H5A20.68620.75820.07430.020*
C10A0.5893 (3)0.8430 (3)0.16644 (19)0.0216 (8)
H10A0.54460.79780.17870.026*
H10B0.54240.90950.14210.026*
C11A0.6066 (3)0.8732 (3)0.23727 (19)0.0209 (8)
H11A0.65010.91950.22490.025*
H11B0.52920.91620.26830.025*
N20.6704 (2)0.7797 (2)0.28121 (15)0.0166 (6)
C1B1.2025 (3)0.6671 (3)0.24645 (18)0.0147 (7)
H1B11.18290.63110.29340.018*
H1B21.12880.70860.22930.018*
C2B1.2479 (3)0.7472 (3)0.26366 (18)0.0146 (7)
H2B11.31920.70940.28390.018*
H2B21.26620.78680.21830.018*
N3B1.1505 (2)0.8227 (2)0.32019 (15)0.0146 (6)
H3B11.08430.85160.30090.017*
H3B21.13610.78300.36130.017*
C3B1.1689 (3)0.9128 (3)0.34500 (19)0.0168 (7)
H3B31.20390.94580.30170.020*
H3B41.22310.88550.37940.020*
C4B1.0518 (3)0.9968 (3)0.38403 (18)0.0152 (7)
C5B1.0453 (3)1.0803 (3)0.42379 (18)0.0181 (7)
H5B1.11431.08540.42900.022*
C6B0.9363 (3)1.1561 (3)0.45574 (18)0.0200 (8)
H6B0.92921.21390.48380.024*
C7B0.8375 (3)1.1468 (3)0.44642 (18)0.0190 (8)
H7B0.76171.19800.46780.023*
C8B0.8519 (3)1.0612 (3)0.40520 (17)0.0152 (7)
N4B0.9575 (2)0.9865 (2)0.37408 (14)0.0149 (6)
C9B0.7490 (3)1.0478 (3)0.39027 (19)0.0188 (7)
H9B10.67951.08330.43010.023*
H9B20.73161.08260.34250.023*
N5B0.7752 (2)0.9310 (2)0.38721 (17)0.0199 (6)
H5B10.78330.90130.43340.024*
H5B20.84550.89730.35470.024*
C10B0.6842 (3)0.9084 (3)0.3636 (2)0.0219 (8)
H10C0.64060.96910.33350.026*
H10D0.62830.90010.40790.026*
C11B0.7444 (3)0.8049 (3)0.31789 (19)0.0167 (7)
H11C0.80970.81010.27950.020*
H11D0.77870.74400.35090.020*
C1C1.3802 (3)0.4979 (3)0.21638 (18)0.0151 (7)
H1C11.42590.53110.23250.018*
H1C21.43140.44910.17440.018*
C2C1.3426 (3)0.4326 (3)0.28035 (18)0.0151 (7)
H2C11.41100.36610.28750.018*
H2C21.31160.47530.32670.018*
N3C1.2513 (2)0.4036 (2)0.26461 (15)0.0134 (6)
H3C11.27450.37680.21710.016*
H3C21.18300.46460.26720.016*
C3C1.2293 (3)0.3211 (3)0.31843 (18)0.0149 (7)
H3C31.29970.25210.31160.018*
H3C41.21260.34600.36990.018*
C4C1.1276 (3)0.3040 (2)0.30575 (17)0.0135 (7)
C5C1.1377 (3)0.2259 (3)0.26024 (18)0.0176 (7)
H5C1.21280.17670.23590.021*
C6C1.0387 (3)0.2187 (3)0.24987 (18)0.0192 (8)
H6C1.04540.16470.21840.023*
C7C0.9286 (3)0.2914 (3)0.28591 (19)0.0181 (7)
H7C0.86010.28700.27910.022*
C8C0.9199 (3)0.3694 (3)0.33130 (17)0.0144 (7)
N4C1.0195 (2)0.3721 (2)0.34011 (15)0.0134 (6)
H4C1.014 (3)0.415 (3)0.370 (2)0.016*
C9C0.8069 (3)0.4511 (3)0.37432 (18)0.0170 (7)
H9C10.74960.41850.38930.020*
H9C20.82070.47090.42000.020*
N5C0.7568 (2)0.5513 (2)0.32931 (15)0.0163 (6)
H5C10.81360.57610.30950.020*
H5C20.73350.53490.29060.020*
C10C0.6542 (3)0.6384 (3)0.37627 (19)0.0182 (7)
H10E0.68160.66250.41390.022*
H10F0.59800.60850.40290.022*
C11C0.5921 (3)0.7354 (3)0.33007 (19)0.0188 (7)
H11E0.55240.71380.29910.023*
H11F0.53120.79290.36410.023*
Cl11.37126 (7)0.44076 (6)0.05127 (4)0.01683 (19)
O1A1.2532 (2)0.4612 (2)0.01323 (15)0.0336 (7)
O1B1.4501 (2)0.3878 (2)0.00286 (13)0.0239 (6)
O1C1.4030 (2)0.37490 (19)0.11585 (14)0.0261 (6)
O1D1.3781 (2)0.54202 (19)0.07669 (13)0.0233 (6)
Cl20.94428 (7)0.99198 (6)0.18214 (4)0.01594 (18)
O2A0.8699 (2)0.9430 (2)0.22414 (15)0.0314 (6)
O2B1.0586 (2)0.9374 (2)0.19777 (14)0.0310 (6)
O2C0.8974 (2)1.10376 (19)0.19951 (14)0.0255 (6)
O2D0.9531 (2)0.98124 (19)0.10332 (13)0.0227 (6)
Cl30.98709 (7)0.62850 (6)0.43328 (4)0.01363 (18)
O3A0.8786 (2)0.6209 (2)0.43590 (15)0.0290 (6)
O3B0.9844 (2)0.72802 (18)0.39691 (13)0.0194 (5)
O3C1.0804 (2)0.53829 (18)0.39068 (13)0.0230 (6)
O3D1.0064 (2)0.62624 (19)0.50605 (13)0.0228 (6)
Cl40.97261 (7)0.59593 (6)0.17288 (4)0.01566 (18)
O4A0.9996 (2)0.5509 (2)0.24295 (15)0.0318 (6)
O4B0.8694 (2)0.58444 (19)0.16525 (13)0.0206 (5)
O4C1.0661 (2)0.5418 (2)0.11188 (15)0.0303 (6)
O4D0.9510 (2)0.70784 (19)0.17057 (13)0.0229 (6)
Cl50.69858 (7)1.03231 (7)0.09514 (5)0.0203 (2)
O5A0.6576 (3)1.1469 (2)0.08597 (16)0.0344 (7)
O5B0.6089 (2)1.0002 (2)0.05227 (15)0.0284 (6)
O5C0.7176 (3)1.0104 (2)0.17190 (15)0.0376 (7)
O5D0.8029 (2)0.9788 (3)0.06772 (18)0.0490 (9)
Cl61.35913 (7)0.58201 (6)0.43736 (4)0.01733 (19)
O6A1.2492 (2)0.6631 (2)0.42476 (14)0.0268 (6)
O6B1.3926 (2)0.6169 (2)0.49442 (15)0.0303 (6)
O6C1.3431 (2)0.4842 (2)0.46069 (14)0.0279 (6)
O6D1.4463 (2)0.5617 (2)0.36967 (14)0.0295 (6)
Cl70.64390 (7)0.92975 (7)0.58632 (5)0.0202 (2)
O7A0.7477 (2)0.8545 (2)0.53767 (15)0.0296 (6)
O7B0.6766 (2)0.9483 (2)0.65039 (15)0.0386 (7)
O7C0.5948 (2)1.0285 (2)0.54793 (16)0.0400 (8)
O7D0.5606 (2)0.8828 (2)0.60946 (17)0.0370 (7)
Cl81.56932 (8)0.16959 (7)0.16125 (5)0.0274 (2)
O8A1.6162 (4)0.1036 (4)0.0987 (3)0.112 (2)
O8B1.6305 (4)0.1187 (4)0.2171 (3)0.0980 (17)
O8C1.5882 (3)0.2652 (2)0.1430 (2)0.0741 (13)
O8D1.4497 (3)0.1949 (3)0.1874 (2)0.0591 (10)
O1W1.2523 (3)0.3431 (2)0.13165 (15)0.0289 (6)
H1WA1.215 (4)0.403 (4)0.112 (2)0.035*
H1WB1.311 (4)0.283 (4)0.108 (2)0.035*
O2W0.6074 (2)0.7995 (2)0.01119 (14)0.0240 (6)
H2WA0.597 (3)0.865 (4)0.025 (2)0.029*
H2WB0.544 (4)0.799 (3)0.008 (2)0.029*
O3W0.6914 (3)0.4730 (3)0.23071 (16)0.0320 (7)
H3WA0.655 (4)0.507 (4)0.199 (3)0.038*
H3WB0.670 (4)0.418 (4)0.240 (2)0.038*
O4W0.6624 (3)0.2979 (3)0.2898 (2)0.0404 (8)
H4WA0.612 (4)0.309 (4)0.336 (3)0.048*
H4WB0.654 (4)0.265 (4)0.260 (3)0.048*
O5W0.4815 (3)0.7277 (3)0.58189 (19)0.0414 (8)
H5WA0.533 (4)0.668 (4)0.564 (3)0.050*
H5WB0.520 (4)0.762 (4)0.592 (3)0.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0113 (13)0.0113 (14)0.0091 (13)0.0032 (11)0.0053 (11)0.0003 (11)
C1A0.0149 (17)0.0162 (17)0.0118 (17)0.0085 (14)0.0039 (13)0.0025 (13)
C2A0.0149 (17)0.0183 (17)0.0116 (17)0.0080 (14)0.0046 (13)0.0002 (13)
N3A0.0147 (14)0.0143 (14)0.0125 (14)0.0072 (12)0.0018 (11)0.0007 (11)
C3A0.0164 (17)0.0149 (17)0.0143 (17)0.0056 (14)0.0005 (14)0.0028 (13)
C4A0.0140 (17)0.0135 (16)0.0091 (16)0.0045 (14)0.0004 (13)0.0030 (13)
C5A0.0171 (18)0.0204 (18)0.0149 (18)0.0052 (15)0.0005 (14)0.0013 (14)
C6A0.0223 (19)0.0185 (18)0.0201 (19)0.0055 (15)0.0017 (15)0.0067 (15)
C7A0.0175 (18)0.0219 (19)0.0218 (19)0.0103 (15)0.0026 (15)0.0017 (15)
C8A0.0140 (17)0.0130 (16)0.0138 (17)0.0043 (14)0.0022 (13)0.0015 (13)
N4A0.0173 (15)0.0122 (14)0.0128 (14)0.0066 (12)0.0010 (12)0.0004 (11)
C9A0.0143 (17)0.0152 (17)0.0193 (18)0.0048 (14)0.0016 (14)0.0003 (14)
N5A0.0149 (14)0.0174 (15)0.0161 (15)0.0068 (12)0.0002 (12)0.0011 (12)
C10A0.0153 (18)0.0237 (19)0.0207 (19)0.0056 (15)0.0012 (14)0.0010 (15)
C11A0.0220 (19)0.0161 (18)0.0188 (19)0.0057 (15)0.0023 (15)0.0015 (14)
N20.0160 (14)0.0146 (14)0.0149 (15)0.0050 (12)0.0022 (11)0.0003 (11)
C1B0.0130 (16)0.0141 (16)0.0134 (17)0.0057 (14)0.0042 (13)0.0004 (13)
C2B0.0120 (16)0.0158 (17)0.0108 (16)0.0037 (14)0.0040 (13)0.0015 (13)
N3B0.0118 (14)0.0130 (14)0.0144 (14)0.0039 (11)0.0038 (11)0.0015 (11)
C3B0.0160 (17)0.0155 (17)0.0164 (17)0.0064 (14)0.0026 (14)0.0035 (14)
C4B0.0186 (18)0.0136 (17)0.0114 (17)0.0076 (14)0.0010 (13)0.0034 (13)
C5B0.0231 (19)0.0164 (17)0.0151 (17)0.0116 (15)0.0018 (14)0.0008 (14)
C6B0.033 (2)0.0119 (17)0.0132 (17)0.0105 (15)0.0023 (15)0.0023 (14)
C7B0.0238 (19)0.0107 (16)0.0131 (17)0.0025 (14)0.0052 (14)0.0019 (13)
C8B0.0175 (17)0.0134 (16)0.0098 (16)0.0047 (14)0.0020 (13)0.0022 (13)
N4B0.0165 (15)0.0109 (14)0.0121 (14)0.0036 (12)0.0026 (11)0.0008 (11)
C9B0.0161 (17)0.0147 (17)0.0176 (18)0.0021 (14)0.0025 (14)0.0005 (14)
N5B0.0122 (14)0.0161 (15)0.0257 (17)0.0022 (12)0.0008 (12)0.0040 (12)
C10B0.0144 (17)0.026 (2)0.0206 (19)0.0058 (15)0.0033 (14)0.0068 (15)
C11B0.0132 (17)0.0142 (17)0.0176 (18)0.0045 (14)0.0039 (14)0.0000 (14)
C1C0.0121 (16)0.0148 (17)0.0169 (17)0.0058 (14)0.0004 (13)0.0001 (13)
C2C0.0153 (17)0.0148 (17)0.0145 (17)0.0067 (14)0.0005 (13)0.0010 (13)
N3C0.0145 (14)0.0113 (14)0.0129 (14)0.0051 (11)0.0013 (11)0.0017 (11)
C3C0.0143 (17)0.0119 (16)0.0148 (17)0.0040 (14)0.0002 (13)0.0031 (13)
C4C0.0171 (17)0.0097 (16)0.0094 (16)0.0042 (13)0.0008 (13)0.0043 (13)
C5C0.0210 (18)0.0118 (17)0.0161 (17)0.0054 (14)0.0011 (14)0.0007 (13)
C6C0.028 (2)0.0164 (18)0.0139 (17)0.0108 (15)0.0015 (15)0.0015 (14)
C7C0.0214 (18)0.0172 (18)0.0184 (18)0.0111 (15)0.0051 (15)0.0046 (14)
C8C0.0176 (17)0.0159 (17)0.0102 (16)0.0091 (14)0.0019 (13)0.0056 (13)
N4C0.0195 (15)0.0110 (14)0.0093 (14)0.0073 (12)0.0002 (11)0.0005 (11)
C9C0.0148 (17)0.0186 (18)0.0152 (17)0.0072 (14)0.0016 (14)0.0006 (14)
N5C0.0143 (14)0.0156 (15)0.0148 (15)0.0052 (12)0.0022 (11)0.0009 (11)
C10C0.0134 (17)0.0178 (18)0.0212 (18)0.0084 (14)0.0055 (14)0.0033 (14)
C11C0.0133 (17)0.0184 (18)0.0208 (19)0.0047 (14)0.0006 (14)0.0015 (14)
Cl10.0151 (4)0.0147 (4)0.0172 (4)0.0063 (3)0.0035 (3)0.0005 (3)
O1A0.0141 (13)0.0365 (16)0.0378 (16)0.0076 (12)0.0066 (11)0.0126 (13)
O1B0.0211 (13)0.0279 (14)0.0228 (14)0.0112 (11)0.0034 (11)0.0019 (11)
O1C0.0361 (15)0.0185 (13)0.0238 (14)0.0108 (12)0.0062 (12)0.0025 (11)
O1D0.0296 (14)0.0154 (12)0.0215 (13)0.0114 (11)0.0061 (11)0.0028 (10)
Cl20.0172 (4)0.0126 (4)0.0151 (4)0.0057 (3)0.0012 (3)0.0004 (3)
O2A0.0369 (16)0.0300 (15)0.0313 (15)0.0252 (13)0.0063 (12)0.0020 (12)
O2B0.0189 (13)0.0436 (17)0.0190 (14)0.0043 (12)0.0026 (11)0.0071 (12)
O2C0.0321 (15)0.0138 (12)0.0303 (15)0.0104 (11)0.0024 (12)0.0047 (11)
O2D0.0301 (14)0.0169 (13)0.0172 (13)0.0066 (11)0.0026 (11)0.0022 (10)
Cl30.0140 (4)0.0120 (4)0.0127 (4)0.0055 (3)0.0007 (3)0.0014 (3)
O3A0.0200 (13)0.0315 (15)0.0412 (16)0.0161 (12)0.0119 (12)0.0140 (12)
O3B0.0183 (12)0.0136 (12)0.0213 (13)0.0063 (10)0.0026 (10)0.0042 (10)
O3C0.0278 (14)0.0136 (12)0.0175 (13)0.0041 (11)0.0071 (11)0.0043 (10)
O3D0.0304 (14)0.0234 (13)0.0129 (12)0.0115 (11)0.0007 (10)0.0005 (10)
Cl40.0133 (4)0.0146 (4)0.0153 (4)0.0052 (3)0.0031 (3)0.0003 (3)
O4A0.0348 (16)0.0375 (16)0.0269 (15)0.0193 (13)0.0129 (12)0.0185 (12)
O4B0.0168 (12)0.0215 (13)0.0217 (13)0.0087 (10)0.0030 (10)0.0053 (10)
O4C0.0190 (13)0.0280 (14)0.0344 (16)0.0072 (11)0.0125 (11)0.0129 (12)
O4D0.0283 (14)0.0163 (13)0.0220 (13)0.0110 (11)0.0012 (11)0.0019 (10)
Cl50.0190 (4)0.0164 (4)0.0230 (5)0.0087 (3)0.0004 (3)0.0054 (3)
O5A0.0520 (18)0.0206 (14)0.0377 (16)0.0228 (13)0.0085 (14)0.0025 (12)
O5B0.0241 (14)0.0236 (14)0.0354 (16)0.0162 (12)0.0075 (11)0.0044 (12)
O5C0.0444 (18)0.0394 (17)0.0256 (15)0.0201 (14)0.0080 (13)0.0087 (13)
O5D0.0214 (15)0.064 (2)0.0477 (19)0.0124 (15)0.0058 (13)0.0332 (16)
Cl60.0143 (4)0.0189 (4)0.0148 (4)0.0044 (3)0.0007 (3)0.0029 (3)
O6A0.0203 (13)0.0271 (14)0.0254 (14)0.0023 (11)0.0060 (11)0.0014 (11)
O6B0.0265 (14)0.0325 (15)0.0291 (15)0.0059 (12)0.0081 (12)0.0108 (12)
O6C0.0344 (15)0.0199 (13)0.0246 (14)0.0117 (12)0.0032 (12)0.0010 (11)
O6D0.0231 (14)0.0414 (16)0.0206 (14)0.0163 (12)0.0110 (11)0.0089 (12)
Cl70.0142 (4)0.0177 (4)0.0220 (4)0.0042 (3)0.0039 (3)0.0000 (3)
O7A0.0184 (13)0.0275 (14)0.0294 (15)0.0011 (11)0.0074 (11)0.0098 (12)
O7B0.0338 (16)0.0480 (18)0.0293 (16)0.0138 (14)0.0001 (13)0.0103 (13)
O7C0.0314 (16)0.0285 (15)0.0370 (17)0.0005 (13)0.0057 (13)0.0160 (13)
O7D0.0217 (14)0.0282 (15)0.059 (2)0.0141 (12)0.0010 (13)0.0026 (14)
Cl80.0211 (5)0.0194 (5)0.0318 (5)0.0025 (4)0.0015 (4)0.0002 (4)
O8A0.076 (3)0.118 (4)0.126 (4)0.032 (3)0.033 (3)0.101 (4)
O8B0.088 (3)0.104 (4)0.138 (4)0.060 (3)0.083 (3)0.076 (3)
O8C0.074 (3)0.0227 (17)0.084 (3)0.0122 (17)0.042 (2)0.0052 (17)
O8D0.0226 (17)0.076 (3)0.065 (2)0.0131 (17)0.0040 (16)0.0039 (19)
O1W0.0356 (16)0.0208 (14)0.0212 (14)0.0034 (13)0.0045 (12)0.0003 (12)
O2W0.0250 (14)0.0196 (14)0.0277 (15)0.0106 (12)0.0048 (12)0.0026 (11)
O3W0.0372 (17)0.0388 (17)0.0250 (15)0.0190 (14)0.0112 (13)0.0038 (13)
O4W0.0352 (17)0.0383 (18)0.049 (2)0.0187 (15)0.0029 (15)0.0072 (15)
O5W0.0343 (18)0.0237 (16)0.059 (2)0.0075 (13)0.0003 (15)0.0132 (15)
Geometric parameters (Å, º) top
N1—C1A1.469 (4)C1C—H1C20.9900
N1—C1B1.469 (4)C2C—N3C1.488 (4)
N1—C1C1.469 (4)C2C—H2C10.9900
C1A—C2A1.514 (5)C2C—H2C20.9900
C1A—H1A10.9900N3C—C3C1.504 (4)
C1A—H1A20.9900N3C—H3C10.9200
C2A—N3A1.496 (4)N3C—H3C20.9200
C2A—H2A10.9900C3C—C4C1.500 (5)
C2A—H2A20.9900C3C—H3C30.9900
N3A—C3A1.505 (4)C3C—H3C40.9900
N3A—H3A10.9200C4C—N4C1.352 (4)
N3A—H3A20.9200C4C—C5C1.372 (5)
C3A—C4A1.508 (5)C5C—C6C1.382 (5)
C3A—H3A30.9900C5C—H5C0.9500
C3A—H3A40.9900C6C—C7C1.397 (5)
C4A—N4A1.353 (4)C6C—H6C0.9500
C4A—C5A1.366 (5)C7C—C8C1.376 (5)
C5A—C6A1.383 (5)C7C—H7C0.9500
C5A—H5A0.9500C8C—N4C1.351 (4)
C6A—C7A1.394 (5)C8C—C9C1.508 (5)
C6A—H6A0.9500N4C—H4C0.82 (4)
C7A—C8A1.374 (5)C9C—N5C1.507 (4)
C7A—H7A0.9500C9C—H9C10.9900
C8A—N4A1.351 (4)C9C—H9C20.9900
C8A—C9A1.512 (4)N5C—C10C1.507 (4)
N4A—H4A0.85 (4)N5C—H5C10.9200
C9A—N5A1.499 (4)N5C—H5C20.9200
C9A—H9A10.9900C10C—C11C1.528 (5)
C9A—H9A20.9900C10C—H10E0.9900
N5A—C10A1.504 (4)C10C—H10F0.9900
N5A—H5A10.9200C11C—H11E0.9900
N5A—H5A20.9200C11C—H11F0.9900
C10A—C11A1.505 (5)Cl1—O1B1.431 (3)
C10A—H10A0.9900Cl1—O1A1.442 (3)
C10A—H10B0.9900Cl1—O1C1.444 (3)
C11A—N21.482 (4)Cl1—O1D1.450 (2)
C11A—H11A0.9900Cl2—O2C1.427 (2)
C11A—H11B0.9900Cl2—O2B1.433 (3)
N2—C11B1.459 (4)Cl2—O2A1.437 (3)
N2—C11C1.479 (4)Cl2—O2D1.456 (2)
C1B—C2B1.532 (5)Cl3—O3D1.423 (2)
C1B—H1B10.9900Cl3—O3A1.438 (3)
C1B—H1B20.9900Cl3—O3C1.447 (2)
C2B—N3B1.500 (4)Cl3—O3B1.448 (2)
C2B—H2B10.9900Cl4—O4D1.434 (2)
C2B—H2B20.9900Cl4—O4C1.434 (3)
N3B—C3B1.484 (4)Cl4—O4A1.435 (3)
N3B—H3B10.9200Cl4—O4B1.447 (2)
N3B—H3B20.9200Cl5—O5D1.424 (3)
C3B—C4B1.523 (4)Cl5—O5C1.426 (3)
C3B—H3B30.9900Cl5—O5A1.442 (3)
C3B—H3B40.9900Cl5—O5B1.447 (2)
C4B—N4B1.339 (4)Cl6—O6B1.422 (3)
C4B—C5B1.383 (5)Cl6—O6D1.436 (2)
C5B—C6B1.382 (5)Cl6—O6A1.442 (3)
C5B—H5B0.9500Cl6—O6C1.448 (3)
C6B—C7B1.387 (5)Cl7—O7C1.426 (3)
C6B—H6B0.9500Cl7—O7B1.428 (3)
C7B—C8B1.385 (5)Cl7—O7D1.437 (3)
C7B—H7B0.9500Cl7—O7A1.458 (3)
C8B—N4B1.346 (4)Cl8—O8A1.393 (4)
C8B—C9B1.506 (5)Cl8—O8B1.399 (4)
C9B—N5B1.491 (4)Cl8—O8D1.405 (3)
C9B—H9B10.9900Cl8—O8C1.423 (3)
C9B—H9B20.9900O1W—H1WA0.85 (5)
N5B—C10B1.498 (4)O1W—H1WB0.91 (5)
N5B—H5B10.9200O2W—H2WA0.87 (4)
N5B—H5B20.9200O2W—H2WB0.81 (4)
C10B—C11B1.526 (5)O3W—H3WA0.82 (5)
C10B—H10C0.9900O3W—H3WB0.90 (5)
C10B—H10D0.9900O4W—H4WA0.92 (5)
C11B—H11C0.9900O4W—H4WB0.79 (5)
C11B—H11D0.9900O5W—H5WA0.84 (5)
C1C—C2C1.524 (4)O5W—H5WB0.87 (5)
C1C—H1C10.9900
C1B—N1—C1A113.6 (2)C11B—C10B—H10D109.9
C1B—N1—C1C114.7 (3)H10C—C10B—H10D108.3
C1A—N1—C1C109.8 (2)N2—C11B—C10B115.8 (3)
N1—C1A—C2A111.0 (3)N2—C11B—H11C108.3
N1—C1A—H1A1109.4C10B—C11B—H11C108.3
C2A—C1A—H1A1109.4N2—C11B—H11D108.3
N1—C1A—H1A2109.4C10B—C11B—H11D108.3
C2A—C1A—H1A2109.4H11C—C11B—H11D107.4
H1A1—C1A—H1A2108.0N1—C1C—C2C112.1 (3)
N3A—C2A—C1A110.2 (3)N1—C1C—H1C1109.2
N3A—C2A—H2A1109.6C2C—C1C—H1C1109.2
C1A—C2A—H2A1109.6N1—C1C—H1C2109.2
N3A—C2A—H2A2109.6C2C—C1C—H1C2109.2
C1A—C2A—H2A2109.6H1C1—C1C—H1C2107.9
H2A1—C2A—H2A2108.1N3C—C2C—C1C110.4 (3)
C2A—N3A—C3A113.1 (2)N3C—C2C—H2C1109.6
C2A—N3A—H3A1109.0C1C—C2C—H2C1109.6
C3A—N3A—H3A1109.0N3C—C2C—H2C2109.6
C2A—N3A—H3A2109.0C1C—C2C—H2C2109.6
C3A—N3A—H3A2109.0H2C1—C2C—H2C2108.1
H3A1—N3A—H3A2107.8C2C—N3C—C3C112.0 (2)
N3A—C3A—C4A111.9 (3)C2C—N3C—H3C1109.2
N3A—C3A—H3A3109.2C3C—N3C—H3C1109.2
C4A—C3A—H3A3109.2C2C—N3C—H3C2109.2
N3A—C3A—H3A4109.2C3C—N3C—H3C2109.2
C4A—C3A—H3A4109.2H3C1—N3C—H3C2107.9
H3A3—C3A—H3A4107.9C4C—C3C—N3C109.9 (3)
N4A—C4A—C5A118.4 (3)C4C—C3C—H3C3109.7
N4A—C4A—C3A117.4 (3)N3C—C3C—H3C3109.7
C5A—C4A—C3A124.2 (3)C4C—C3C—H3C4109.7
C4A—C5A—C6A119.6 (3)N3C—C3C—H3C4109.7
C4A—C5A—H5A120.2H3C3—C3C—H3C4108.2
C6A—C5A—H5A120.2N4C—C4C—C5C118.5 (3)
C5A—C6A—C7A120.5 (3)N4C—C4C—C3C117.5 (3)
C5A—C6A—H6A119.8C5C—C4C—C3C124.0 (3)
C7A—C6A—H6A119.8C4C—C5C—C6C120.0 (3)
C8A—C7A—C6A118.8 (3)C4C—C5C—H5C120.0
C8A—C7A—H7A120.6C6C—C5C—H5C120.0
C6A—C7A—H7A120.6C5C—C6C—C7C119.7 (3)
N4A—C8A—C7A118.8 (3)C5C—C6C—H6C120.2
N4A—C8A—C9A115.1 (3)C7C—C6C—H6C120.2
C7A—C8A—C9A126.1 (3)C8C—C7C—C6C119.7 (3)
C8A—N4A—C4A123.8 (3)C8C—C7C—H7C120.2
C8A—N4A—H4A119 (2)C6C—C7C—H7C120.2
C4A—N4A—H4A117 (2)N4C—C8C—C7C118.2 (3)
N5A—C9A—C8A112.3 (3)N4C—C8C—C9C116.9 (3)
N5A—C9A—H9A1109.1C7C—C8C—C9C124.9 (3)
C8A—C9A—H9A1109.1C8C—N4C—C4C124.0 (3)
N5A—C9A—H9A2109.1C8C—N4C—H4C118 (3)
C8A—C9A—H9A2109.1C4C—N4C—H4C118 (3)
H9A1—C9A—H9A2107.9N5C—C9C—C8C111.8 (3)
C9A—N5A—C10A114.3 (3)N5C—C9C—H9C1109.2
C9A—N5A—H5A1108.7C8C—C9C—H9C1109.2
C10A—N5A—H5A1108.7N5C—C9C—H9C2109.2
C9A—N5A—H5A2108.7C8C—C9C—H9C2109.2
C10A—N5A—H5A2108.7H9C1—C9C—H9C2107.9
H5A1—N5A—H5A2107.6C10C—N5C—C9C111.2 (2)
N5A—C10A—C11A113.1 (3)C10C—N5C—H5C1109.4
N5A—C10A—H10A109.0C9C—N5C—H5C1109.4
C11A—C10A—H10A109.0C10C—N5C—H5C2109.4
N5A—C10A—H10B109.0C9C—N5C—H5C2109.4
C11A—C10A—H10B109.0H5C1—N5C—H5C2108.0
H10A—C10A—H10B107.8N5C—C10C—C11C112.3 (3)
N2—C11A—C10A114.1 (3)N5C—C10C—H10E109.2
N2—C11A—H11A108.7C11C—C10C—H10E109.2
C10A—C11A—H11A108.7N5C—C10C—H10F109.2
N2—C11A—H11B108.7C11C—C10C—H10F109.2
C10A—C11A—H11B108.7H10E—C10C—H10F107.9
H11A—C11A—H11B107.6N2—C11C—C10C114.1 (3)
C11B—N2—C11C115.3 (3)N2—C11C—H11E108.7
C11B—N2—C11A110.6 (3)C10C—C11C—H11E108.7
C11C—N2—C11A112.2 (3)N2—C11C—H11F108.7
N1—C1B—C2B117.4 (3)C10C—C11C—H11F108.7
N1—C1B—H1B1107.9H11E—C11C—H11F107.6
C2B—C1B—H1B1107.9O1B—Cl1—O1A110.40 (15)
N1—C1B—H1B2107.9O1B—Cl1—O1C110.06 (15)
C2B—C1B—H1B2107.9O1A—Cl1—O1C109.44 (17)
H1B1—C1B—H1B2107.2O1B—Cl1—O1D109.86 (15)
N3B—C2B—C1B105.1 (2)O1A—Cl1—O1D109.34 (15)
N3B—C2B—H2B1110.7O1C—Cl1—O1D107.69 (14)
C1B—C2B—H2B1110.7O2C—Cl2—O2B110.35 (17)
N3B—C2B—H2B2110.7O2C—Cl2—O2A110.75 (16)
C1B—C2B—H2B2110.7O2B—Cl2—O2A109.33 (17)
H2B1—C2B—H2B2108.8O2C—Cl2—O2D108.66 (15)
C3B—N3B—C2B116.8 (2)O2B—Cl2—O2D108.67 (15)
C3B—N3B—H3B1108.1O2A—Cl2—O2D109.03 (16)
C2B—N3B—H3B1108.1O3D—Cl3—O3A110.87 (15)
C3B—N3B—H3B2108.1O3D—Cl3—O3C109.84 (15)
C2B—N3B—H3B2108.1O3A—Cl3—O3C108.16 (16)
H3B1—N3B—H3B2107.3O3D—Cl3—O3B109.31 (15)
N3B—C3B—C4B109.0 (3)O3A—Cl3—O3B109.39 (14)
N3B—C3B—H3B3109.9O3C—Cl3—O3B109.23 (14)
C4B—C3B—H3B3109.9O4D—Cl4—O4C108.81 (15)
N3B—C3B—H3B4109.9O4D—Cl4—O4A109.45 (16)
C4B—C3B—H3B4109.9O4C—Cl4—O4A111.76 (17)
H3B3—C3B—H3B4108.3O4D—Cl4—O4B109.79 (15)
N4B—C4B—C5B123.2 (3)O4C—Cl4—O4B108.46 (15)
N4B—C4B—C3B115.5 (3)O4A—Cl4—O4B108.56 (15)
C5B—C4B—C3B121.2 (3)O5D—Cl5—O5C111.70 (19)
C6B—C5B—C4B118.5 (3)O5D—Cl5—O5A108.8 (2)
C6B—C5B—H5B120.8O5C—Cl5—O5A108.56 (17)
C4B—C5B—H5B120.8O5D—Cl5—O5B109.78 (17)
C5B—C6B—C7B119.3 (3)O5C—Cl5—O5B110.13 (17)
C5B—C6B—H6B120.3O5A—Cl5—O5B107.72 (16)
C7B—C6B—H6B120.3O6B—Cl6—O6D111.04 (16)
C8B—C7B—C6B118.4 (3)O6B—Cl6—O6A109.55 (16)
C8B—C7B—H7B120.8O6D—Cl6—O6A109.73 (16)
C6B—C7B—H7B120.8O6B—Cl6—O6C109.43 (17)
N4B—C8B—C7B122.9 (3)O6D—Cl6—O6C109.19 (16)
N4B—C8B—C9B115.4 (3)O6A—Cl6—O6C107.84 (16)
C7B—C8B—C9B121.6 (3)O7C—Cl7—O7B110.16 (19)
C4B—N4B—C8B117.6 (3)O7C—Cl7—O7D110.31 (18)
N5B—C9B—C8B110.0 (3)O7B—Cl7—O7D108.83 (18)
N5B—C9B—H9B1109.7O7C—Cl7—O7A109.70 (16)
C8B—C9B—H9B1109.7O7B—Cl7—O7A108.61 (17)
N5B—C9B—H9B2109.7O7D—Cl7—O7A109.20 (16)
C8B—C9B—H9B2109.7O8A—Cl8—O8B109.5 (4)
H9B1—C9B—H9B2108.2O8A—Cl8—O8D111.8 (3)
C9B—N5B—C10B114.3 (3)O8B—Cl8—O8D110.2 (3)
C9B—N5B—H5B1108.7O8A—Cl8—O8C108.7 (3)
C10B—N5B—H5B1108.7O8B—Cl8—O8C106.0 (3)
C9B—N5B—H5B2108.7O8D—Cl8—O8C110.5 (2)
C10B—N5B—H5B2108.7H1WA—O1W—H1WB127 (4)
H5B1—N5B—H5B2107.6H2WA—O2W—H2WB103 (4)
N5B—C10B—C11B108.8 (3)H3WA—O3W—H3WB102 (4)
N5B—C10B—H10C109.9H4WA—O4W—H4WB117 (5)
C11B—C10B—H10C109.9H5WA—O5W—H5WB105 (5)
N5B—C10B—H10D109.9
C1B—N1—C1A—C2A60.2 (3)C6B—C7B—C8B—C9B177.8 (3)
C1C—N1—C1A—C2A169.9 (3)C5B—C4B—N4B—C8B0.6 (5)
N1—C1A—C2A—N3A175.5 (2)C3B—C4B—N4B—C8B177.6 (3)
C1A—C2A—N3A—C3A175.5 (3)C7B—C8B—N4B—C4B0.0 (5)
C2A—N3A—C3A—C4A54.6 (3)C9B—C8B—N4B—C4B178.2 (3)
N3A—C3A—C4A—N4A106.1 (3)N4B—C8B—C9B—N5B35.2 (4)
N3A—C3A—C4A—C5A72.3 (4)C7B—C8B—C9B—N5B146.6 (3)
N4A—C4A—C5A—C6A1.7 (5)C8B—C9B—N5B—C10B173.0 (3)
C3A—C4A—C5A—C6A176.7 (3)C9B—N5B—C10B—C11B145.1 (3)
C4A—C5A—C6A—C7A1.8 (5)C11C—N2—C11B—C10B76.8 (4)
C5A—C6A—C7A—C8A0.3 (5)C11A—N2—C11B—C10B51.9 (4)
C6A—C7A—C8A—N4A2.3 (5)N5B—C10B—C11B—N2171.2 (3)
C6A—C7A—C8A—C9A176.6 (3)C1B—N1—C1C—C2C64.3 (3)
C7A—C8A—N4A—C4A2.5 (5)C1A—N1—C1C—C2C166.3 (3)
C9A—C8A—N4A—C4A176.5 (3)N1—C1C—C2C—N3C45.4 (4)
C5A—C4A—N4A—C8A0.5 (5)C1C—C2C—N3C—C3C168.5 (3)
C3A—C4A—N4A—C8A178.9 (3)C2C—N3C—C3C—C4C173.5 (3)
N4A—C8A—C9A—N5A151.6 (3)N3C—C3C—C4C—N4C85.5 (3)
C7A—C8A—C9A—N5A29.4 (5)N3C—C3C—C4C—C5C92.8 (4)
C8A—C9A—N5A—C10A178.4 (3)N4C—C4C—C5C—C6C0.6 (5)
C9A—N5A—C10A—C11A66.8 (4)C3C—C4C—C5C—C6C177.7 (3)
N5A—C10A—C11A—N261.9 (4)C4C—C5C—C6C—C7C0.0 (5)
C10A—C11A—N2—C11B144.9 (3)C5C—C6C—C7C—C8C0.1 (5)
C10A—C11A—N2—C11C84.8 (3)C6C—C7C—C8C—N4C0.8 (5)
C1A—N1—C1B—C2B55.2 (4)C6C—C7C—C8C—C9C178.8 (3)
C1C—N1—C1B—C2B72.3 (3)C7C—C8C—N4C—C4C1.5 (5)
N1—C1B—C2B—N3B179.2 (3)C9C—C8C—N4C—C4C179.7 (3)
C1B—C2B—N3B—C3B177.5 (3)C5C—C4C—N4C—C8C1.4 (5)
C2B—N3B—C3B—C4B164.1 (3)C3C—C4C—N4C—C8C177.0 (3)
N3B—C3B—C4B—N4B14.1 (4)N4C—C8C—C9C—N5C93.5 (3)
N3B—C3B—C4B—C5B168.8 (3)C7C—C8C—C9C—N5C88.5 (4)
N4B—C4B—C5B—C6B0.9 (5)C8C—C9C—N5C—C10C171.5 (3)
C3B—C4B—C5B—C6B177.7 (3)C9C—N5C—C10C—C11C172.6 (3)
C4B—C5B—C6B—C7B0.7 (5)C11B—N2—C11C—C10C52.4 (4)
C5B—C6B—C7B—C8B0.1 (5)C11A—N2—C11C—C10C179.7 (3)
C6B—C7B—C8B—N4B0.2 (5)N5C—C10C—C11C—N252.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A1···O1D0.921.932.850 (4)173
N3A—H3A2···O5Ai0.922.112.889 (4)142
N4A—H4A···O2D0.85 (4)1.91 (4)2.755 (4)173 (4)
N5A—H5A1···O4B0.922.012.914 (4)167
N5A—H5A2···O2W0.921.992.798 (4)146
N5A—H5A2···O1Cii0.922.512.987 (4)113
N3B—H3B1···O2B0.922.162.829 (4)129
N3B—H3B2···O6A0.922.152.850 (4)132
N3B—H3B2···O3B0.922.322.974 (3)128
N5B—H5B1···O7A0.921.982.874 (4)162
N5B—H5B2···O2A0.922.422.998 (4)121
N5B—H5B2···O3B0.922.452.976 (4)117
N3C—H3C1···O1W0.921.812.672 (4)155
N3C—H3C1···O8D0.922.563.114 (4)119
N3C—H3C2···O4A0.922.293.121 (4)150
N3C—H3C2···O3C0.922.432.956 (4)116
N4C—H4C···O3C0.82 (4)2.29 (4)2.991 (4)145 (3)
N5C—H5C1···O4A0.922.333.168 (4)152
N5C—H5C1···O4B0.922.603.125 (4)116
N5C—H5C2···O3W0.921.762.661 (4)165
O1W—H1WA···O4C0.85 (5)2.06 (5)2.833 (4)151 (4)
O1W—H1WA···O1A0.85 (5)2.39 (4)2.992 (4)129 (4)
O1W—H1WB···O2Wii0.91 (5)2.03 (5)2.840 (4)147 (4)
O2W—H2WA···O5B0.87 (4)1.92 (5)2.781 (4)167 (4)
O2W—H2WB···O1Bii0.81 (4)2.51 (4)2.927 (4)113 (3)
O2W—H2WB···O5Aiii0.81 (4)2.62 (4)3.281 (4)140 (4)
O3W—H3WA···O1Cii0.82 (5)2.14 (5)2.924 (4)160 (4)
O3W—H3WA···O1Dii0.82 (5)2.61 (5)3.237 (4)135 (4)
O3W—H3WB···O4W0.90 (5)1.83 (5)2.667 (4)155 (4)
O4W—H4WA···O5Wiv0.92 (5)1.89 (5)2.746 (5)155 (4)
O4W—H4WB···O8Bv0.79 (5)2.39 (5)3.127 (6)155 (5)
O4W—H4WB···O8Cv0.79 (5)2.51 (5)3.218 (6)149 (5)
O5W—H5WA···O6Cvi0.84 (5)2.04 (5)2.871 (4)171 (5)
O5W—H5WB···O7D0.87 (5)2.00 (5)2.846 (4)161 (5)
Symmetry codes: (i) x+2, y+2, z; (ii) x+2, y+1, z; (iii) x+1, y+2, z; (iv) x+1, y+1, z+1; (v) x1, y, z; (vi) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC33H59N118+·8ClO4·5H2O
Mr1495.59
Crystal system, space groupTriclinic, P1
Temperature (K)128
a, b, c (Å)12.9265 (13), 13.6798 (14), 18.5310 (19)
α, β, γ (°)84.258 (9), 76.394 (8), 65.092 (8)
V3)2888.7 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.50
Crystal size (mm)0.82 × 0.52 × 0.36
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correctionψ scan
(SHELXTL/PC; Siemens, 1990b)
Tmin, Tmax0.862, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
9513, 9055, 7315
Rint0.105
θmax (°)24.0
(sin θ/λ)max1)0.572
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.113, 1.03
No. of reflections9055
No. of parameters838
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.65, 0.67

Computer programs: XSCANS (Siemens, 1990a), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A1···O1D0.921.932.850 (4)173
N3A—H3A2···O5Ai0.922.112.889 (4)142
N4A—H4A···O2D0.85 (4)1.91 (4)2.755 (4)173 (4)
N5A—H5A1···O4B0.922.012.914 (4)167
N5A—H5A2···O2W0.921.992.798 (4)146
N5A—H5A2···O1Cii0.922.512.987 (4)113
N3B—H3B1···O2B0.922.162.829 (4)129
N3B—H3B2···O6A0.922.152.850 (4)132
N3B—H3B2···O3B0.922.322.974 (3)128
N5B—H5B1···O7A0.921.982.874 (4)162
N5B—H5B2···O2A0.922.422.998 (4)121
N5B—H5B2···O3B0.922.452.976 (4)117
N3C—H3C1···O1W0.921.812.672 (4)155
N3C—H3C1···O8D0.922.563.114 (4)119
N3C—H3C2···O4A0.922.293.121 (4)150
N3C—H3C2···O3C0.922.432.956 (4)116
N4C—H4C···O3C0.82 (4)2.29 (4)2.991 (4)145 (3)
N5C—H5C1···O4A0.922.333.168 (4)152
N5C—H5C1···O4B0.922.603.125 (4)116
N5C—H5C2···O3W0.921.762.661 (4)165
O1W—H1WA···O4C0.85 (5)2.06 (5)2.833 (4)151 (4)
O1W—H1WA···O1A0.85 (5)2.39 (4)2.992 (4)129 (4)
O1W—H1WB···O2Wii0.91 (5)2.03 (5)2.840 (4)147 (4)
O2W—H2WA···O5B0.87 (4)1.92 (5)2.781 (4)167 (4)
O2W—H2WB···O1Bii0.81 (4)2.51 (4)2.927 (4)113 (3)
O2W—H2WB···O5Aiii0.81 (4)2.62 (4)3.281 (4)140 (4)
O3W—H3WA···O1Cii0.82 (5)2.14 (5)2.924 (4)160 (4)
O3W—H3WA···O1Dii0.82 (5)2.61 (5)3.237 (4)135 (4)
O3W—H3WB···O4W0.90 (5)1.83 (5)2.667 (4)155 (4)
O4W—H4WA···O5Wiv0.92 (5)1.89 (5)2.746 (5)155 (4)
O4W—H4WB···O8Bv0.79 (5)2.39 (5)3.127 (6)155 (5)
O4W—H4WB···O8Cv0.79 (5)2.51 (5)3.218 (6)149 (5)
O5W—H5WA···O6Cvi0.84 (5)2.04 (5)2.871 (4)171 (5)
O5W—H5WB···O7D0.87 (5)2.00 (5)2.846 (4)161 (5)
Symmetry codes: (i) x+2, y+2, z; (ii) x+2, y+1, z; (iii) x+1, y+2, z; (iv) x+1, y+1, z+1; (v) x1, y, z; (vi) x+2, y+1, z+1.
 

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