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Three polymorphs of a calix[4]arene fixed in the 1,3-alternate conformation by two bridges, a crown-6 on one side and a crown-6 including a photoisomerizable azobenzene unit on the other, 8,11,14,28,31,34,37,40,43,57,60,63-do­deca­oxa­-2,3-diaza­nona­cyclo­[62.2.2.24,7.116,45.126,55.015,20.022,27.044,49.051,56]doheptaconta-1(66),2,4,6,15,17,19,22,24,26,44,46,48,51,53,55,64,67,69-nonadec­ene, have been characterized by single-crystal X-ray diffraction. In all the polymorphs the azobenzene group is in the more stable trans conformation. The polymorphism arises from the high conformational flexibility of the bridges, which are arranged differently and are highly disordered in the two monoclinic forms (1) and (2a). Form (2a) presents a phase transition near 268 (2) K, leading to a triclinic form (2b), differing from the high-temperature form by some ordering of the chains and a subsequent reduction in crystallographic site multiplicity. The evolution of the cell parameters and peak width with temperature has been investigated down to 173 (2) K. Adiabatic calorimetry measurements indicate a smooth transition centered at 265.0 (1) K, with a heat capacity jump of 60 mJ g-1 K-1, suggesting a second-order nature for the transition.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 1, 2a, 2b

hkl

Structure factor file (CIF format)
Contains datablock 1

hkl

Structure factor file (CIF format)
Contains datablock 2a

hkl

Structure factor file (CIF format)
Contains datablock 2b

CCDC references: 131741; 131742; 131743

Computing details top

For all compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software (Enraf-Nonius, 1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: SHELXTL (Sheldrick, 1993); software used to prepare material for publication: SHELXTL (Sheldrick, 1993).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(1) top
Crystal data top
C58H64N2O12F(000) = 2088
Mr = 981.11Dx = 1.267 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 13.667 (4) ÅCell parameters from 25 reflections
b = 18.647 (11) Åθ = 8–12°
c = 20.188 (6) ŵ = 0.09 mm1
β = 90.72 (2)°T = 243 K
V = 5145 (4) Å3Parallelepiped, orange
Z = 40.70 × 0.60 × 0.50 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.02
Radiation source: fine-focus sealed tubeθmax = 22°, θmin = 1°
Graphite monochromatorh = 014
ω/2θ scansk = 019
6514 measured reflectionsl = 2121
6301 independent reflections3 standard reflections every 60 min
2449 reflections with I > 2σ(I) intensity decay: 4.7%
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)] = 0.127Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.385H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.1798P)2 + 16.015P],
where P = (Fo2 + 2Fc2)/3
4701 reflections(Δ/σ)max = 0.019
628 parametersΔρmax = 1.49 e Å3
79 restraintsΔρmin = 0.60 e Å3
Crystal data top
C58H64N2O12V = 5145 (4) Å3
Mr = 981.11Z = 4
Monoclinic, P21/aMo Kα radiation
a = 13.667 (4) ŵ = 0.09 mm1
b = 18.647 (11) ÅT = 243 K
c = 20.188 (6) Å0.70 × 0.60 × 0.50 mm
β = 90.72 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.02
6514 measured reflectionsθmax = 22°
6301 independent reflections3 standard reflections every 60 min
2449 reflections with I > 2σ(I) intensity decay: 4.7%
Refinement top
R[F2 > 2σ(F2)] = 0.12779 restraints
wR(F2) = 0.385H-atom parameters constrained
S = 1.11Δρmax = 1.49 e Å3
4701 reflectionsΔρmin = 0.60 e Å3
628 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. All atoms refined anisotropically, unless those of the disordered parts of the molecule that were refined isotropically, with occupation factors constrained to sum to unity. The occupation factors have been constrained to be equal for atoms in the same fragment of disordered parts. The low data quality resulted in some non physical bond lengths and angles in the disordered parts of the molecule, hence those bond lengths were restrained to the usual values: O—C 1.426 (10) A, N-Car. 1.43 (1) A and C—C 1.53 (1) A; some 1···3 distances were also restrained (C···O 2.39 (1), C···C 2.36 (1) A) so as to restrain the bond angles around C(23), C(24 A), C(24B), C(26 A), C(26B), C(27 A), C(27B) and C(29). The structure is particularly unsatisfying for the diazobenzene moiety: the two nitrogen atoms have been found, but, being unstable on refinement, they were fixed in the last refinement cycles with an isotropic displacement factor set to 0.15; the N—N distance is nevertheless shorter than usual. The bond distances in the two benzenic rings have been restrained to Car-Car 1.39 (1) A. The last Fourier map presents a single peak at 1.49 e/A3 that could be attributed to a second position for N(1), in agreement with high values of the displacement parameters for the benzenic rings (C(5)—C(16)): two positions of N(1) and of one aromatic ring (C(5)—C(10)), symmetrical with respect to the C—N(2) bond direction and both corresponding to trans geometries, could exist, but the poor data did not enable to resolve this disorder. Hydrogen atoms were introduced, unless for the disordered parts, at calculated positions and constrained to ride on their parent carbon atoms (C—H 0.97 A for CH2, 0.93 A for Car·H, displacement factor equal to 1.2 times that of the parent carbon atom). Refinement on F2 for all reflections except those with very negative F2 or flagged for rejection. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.0606 (7)0.0561 (7)0.7024 (5)0.095 (3)
O20.0060 (8)0.1197 (7)0.5719 (6)0.119 (4)
O30.1031 (9)0.1084 (7)0.4428 (5)0.105 (4)
O40.7809 (7)0.1316 (7)0.7837 (6)0.105 (4)
O50.6100 (7)0.1667 (5)0.8658 (4)0.074 (3)
O60.4234 (6)0.0695 (5)0.8870 (4)0.071 (3)
O70.3796 (6)0.0714 (5)0.6844 (4)0.067 (2)
O80.3940 (9)0.2168 (6)0.6361 (5)0.117 (4)
O9A0.3056 (12)0.3212 (7)0.7756 (7)0.063 (8)*0.49 (3)
O9B0.2386 (14)0.3188 (9)0.7435 (11)0.138 (12)*0.51 (3)
O10A0.1754 (15)0.3690 (11)0.8819 (9)0.144 (10)*0.58 (2)
O10B0.2716 (16)0.3211 (12)0.8776 (9)0.108 (11)*0.41 (2)
O110.1182 (8)0.2084 (5)0.9732 (5)0.101 (3)
O120.1126 (6)0.0695 (5)0.9141 (4)0.059 (2)
N10.48600.11140.55520.150*
N20.53140.14570.58570.150*
C1A0.0310 (13)0.0878 (15)0.6834 (11)0.083 (11)*0.58 (4)
C1B0.0278 (18)0.0479 (18)0.6634 (17)0.083 (14)*0.42 (4)
C2A0.047 (2)0.0690 (14)0.6104 (10)0.094 (12)*0.58 (4)
C2B0.057 (2)0.1171 (18)0.6275 (13)0.088 (16)*0.42 (4)
C30.0417 (11)0.1133 (9)0.5091 (7)0.104 (5)
H3A0.0483 (11)0.0633 (9)0.4966 (7)0.125*
H3B0.1063 (11)0.1348 (9)0.5101 (7)0.125*
C40.0235 (11)0.1530 (9)0.4606 (8)0.096 (5)
H4A0.0479 (11)0.1967 (9)0.4810 (8)0.115*
H4B0.0141 (11)0.1660 (9)0.4214 (8)0.115*
C50.1951 (10)0.1249 (9)0.4707 (7)0.092 (4)
C60.2343 (11)0.1870 (9)0.5011 (9)0.127 (6)
H60.1980 (11)0.2289 (9)0.5056 (9)0.152*
C70.3328 (9)0.1817 (9)0.5244 (9)0.136 (7)
H70.3576 (9)0.2227 (9)0.5448 (9)0.163*
C80.3957 (12)0.1256 (9)0.5211 (11)0.166 (9)
C90.3503 (10)0.0692 (11)0.4905 (8)0.133 (7)
H90.3872 (10)0.0275 (11)0.4871 (8)0.160*
C100.2565 (10)0.0658 (10)0.4639 (8)0.105 (5)
H100.2350 (10)0.0249 (10)0.4418 (8)0.126*
C110.6007 (8)0.1503 (7)0.6343 (6)0.157 (12)
C120.6191 (13)0.2123 (7)0.6697 (8)0.149 (10)
H120.5910 (13)0.2555 (7)0.6566 (8)0.179*
C130.6780 (11)0.2095 (8)0.7229 (7)0.101 (5)
H130.6897 (11)0.2479 (8)0.7513 (7)0.121*
C140.7186 (10)0.1432 (8)0.7305 (7)0.085 (5)
C150.7102 (9)0.0806 (8)0.6967 (6)0.094 (5)
H150.7439 (9)0.0389 (8)0.7080 (6)0.112*
C160.6488 (9)0.0858 (6)0.6461 (7)0.128 (7)
H160.6378 (9)0.0466 (6)0.6185 (7)0.154*
C170.7755 (12)0.1816 (9)0.8366 (8)0.103 (5)
H17A0.8396 (12)0.1882 (9)0.8568 (8)0.124*
H17B0.7528 (12)0.2276 (9)0.8201 (8)0.124*
C180.7054 (11)0.1528 (9)0.8866 (8)0.093 (5)
H18A0.7177 (11)0.1752 (9)0.9292 (8)0.111*
H18B0.7148 (11)0.1015 (9)0.8915 (8)0.111*
C190.5399 (11)0.1611 (8)0.9172 (8)0.089 (5)
H19A0.5691 (11)0.1796 (8)0.9578 (8)0.106*
H19B0.4846 (11)0.1916 (8)0.9060 (8)0.106*
C200.5020 (12)0.0861 (8)0.9307 (8)0.084 (5)
H20A0.4800 (12)0.0830 (8)0.9761 (8)0.101*
H20B0.5543 (12)0.0517 (8)0.9249 (8)0.101*
C210.4332 (11)0.0904 (8)0.6280 (7)0.087 (5)
H21A0.3919 (11)0.0862 (8)0.5888 (7)0.104*
H21B0.4883 (11)0.0581 (8)0.6232 (7)0.104*
C220.4690 (12)0.1647 (9)0.6345 (9)0.116 (7)
H22A0.5079 (12)0.1685 (9)0.6748 (9)0.139*
H22B0.5114 (12)0.1751 (9)0.5976 (9)0.139*
C230.3589 (13)0.2354 (7)0.6993 (6)0.124 (7)
C24A0.328 (3)0.3114 (9)0.7062 (9)0.077 (11)*0.49 (3)
C24B0.279 (3)0.294 (2)0.6838 (10)0.110 (15)*0.51 (3)
C250.2545 (11)0.3868 (6)0.7769 (6)0.102 (6)
C26A0.2542 (15)0.4041 (12)0.8509 (8)0.092 (9)*0.58 (2)
C26B0.218 (2)0.3782 (19)0.8470 (11)0.104 (13)*0.41 (2)
C27A0.188 (2)0.2969 (12)0.9046 (15)0.099 (10)*0.58 (2)
C27B0.225 (2)0.2945 (16)0.9349 (10)0.080 (11)*0.41 (2)
C28A0.107 (2)0.2812 (10)0.9548 (16)0.137 (14)*0.58 (2)
C28B0.142 (2)0.2442 (16)0.9128 (10)0.088 (12)*0.41 (2)
C290.0305 (9)0.1678 (6)0.9668 (9)0.095 (5)
C30A0.061 (2)0.0881 (6)0.9735 (10)0.099 (19)*0.50
C30B0.0540 (19)0.0884 (6)0.9695 (12)0.067 (17)*0.50
C310.0795 (10)0.0159 (10)0.7127 (8)0.076 (4)
C320.0341 (9)0.0507 (10)0.7656 (8)0.074 (4)
C330.0485 (10)0.1223 (11)0.7722 (7)0.081 (5)
H330.0159 (10)0.1473 (11)0.8051 (7)0.097*
C340.1105 (13)0.1585 (10)0.7308 (9)0.098 (5)
H340.1207 (13)0.2074 (10)0.7363 (9)0.118*
C350.1585 (10)0.1209 (11)0.6800 (8)0.088 (5)
H350.1998 (10)0.1455 (11)0.6517 (8)0.105*
C360.1453 (10)0.0508 (10)0.6723 (7)0.071 (4)
C370.2066 (10)0.0065 (9)0.6243 (7)0.086 (5)
H37A0.2360 (10)0.0380 (9)0.5919 (7)0.103*
H37B0.1649 (10)0.0274 (9)0.6009 (7)0.103*
C380.2873 (10)0.0342 (8)0.6626 (6)0.066 (4)
C390.3662 (10)0.0017 (8)0.6936 (7)0.064 (4)
C400.4311 (9)0.0396 (7)0.7331 (6)0.055 (3)
C410.4168 (11)0.1134 (8)0.7395 (8)0.077 (4)
H410.4576 (11)0.1398 (8)0.7675 (8)0.092*
C420.3451 (13)0.1467 (8)0.7059 (9)0.085 (5)
H420.3411 (13)0.1964 (8)0.7073 (9)0.102*
C430.2766 (11)0.1084 (11)0.6688 (7)0.079 (5)
H430.2243 (11)0.1319 (11)0.6484 (7)0.095*
C440.5043 (8)0.0006 (7)0.7755 (7)0.067 (4)
H44A0.5408 (8)0.0328 (7)0.7485 (7)0.080*
H44B0.5501 (8)0.0347 (7)0.7949 (7)0.080*
C450.4522 (8)0.0403 (8)0.8307 (6)0.061 (4)
C460.4068 (8)0.0039 (7)0.8818 (6)0.053 (3)
C470.3446 (9)0.0370 (7)0.9243 (6)0.061 (3)
C480.3301 (10)0.1092 (9)0.9185 (7)0.071 (4)
H480.2856 (10)0.1321 (9)0.9458 (7)0.085*
C490.3811 (11)0.1481 (8)0.8726 (8)0.075 (4)
H490.3745 (11)0.1977 (8)0.8708 (8)0.090*
C500.4422 (10)0.1132 (7)0.8290 (7)0.072 (4)
H500.4769 (10)0.1397 (7)0.7981 (7)0.086*
C510.2743 (11)0.0068 (8)0.9680 (7)0.077 (4)
H51A0.3120 (11)0.0426 (8)0.9921 (7)0.092*
H51B0.2455 (11)0.0251 (8)1.0003 (7)0.092*
C520.1946 (11)0.0433 (8)0.9309 (6)0.063 (4)
C530.1197 (11)0.0034 (7)0.9019 (7)0.062 (4)
C540.0504 (10)0.0342 (8)0.8590 (8)0.073 (4)
C550.0564 (12)0.1072 (9)0.8491 (8)0.080 (4)
H550.0098 (12)0.1289 (9)0.8217 (8)0.097*
C560.1268 (14)0.1489 (8)0.8772 (10)0.094 (5)
H560.1284 (14)0.1979 (8)0.8690 (10)0.113*
C570.1956 (15)0.1174 (10)0.9179 (9)0.100 (6)
H570.2440 (15)0.1458 (10)0.9374 (9)0.120*
C580.0204 (10)0.0125 (9)0.8201 (8)0.084 (5)
H58A0.0500 (10)0.0474 (9)0.8493 (8)0.101*
H58B0.0720 (10)0.0169 (9)0.8010 (8)0.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.059 (6)0.135 (10)0.091 (8)0.031 (6)0.002 (5)0.025 (7)
O20.100 (8)0.163 (12)0.093 (8)0.009 (8)0.019 (7)0.039 (8)
O30.102 (8)0.136 (10)0.075 (7)0.015 (8)0.003 (7)0.013 (7)
O40.054 (6)0.143 (11)0.119 (9)0.028 (6)0.004 (6)0.007 (8)
O50.056 (6)0.090 (7)0.075 (6)0.012 (5)0.005 (5)0.003 (5)
O60.071 (6)0.072 (7)0.071 (6)0.017 (5)0.003 (5)0.005 (5)
O70.067 (6)0.070 (6)0.066 (6)0.001 (5)0.024 (5)0.005 (5)
O80.161 (12)0.097 (8)0.095 (8)0.006 (8)0.050 (8)0.018 (7)
O110.123 (9)0.093 (8)0.087 (8)0.006 (7)0.001 (7)0.002 (6)
O120.057 (5)0.063 (6)0.058 (5)0.004 (4)0.023 (4)0.003 (4)
C30.100 (13)0.106 (13)0.107 (14)0.016 (11)0.022 (12)0.015 (12)
C40.099 (13)0.115 (14)0.074 (11)0.008 (12)0.024 (10)0.017 (10)
C50.082 (10)0.132 (12)0.063 (10)0.028 (7)0.002 (8)0.013 (9)
C60.167 (14)0.097 (11)0.117 (16)0.021 (11)0.003 (13)0.021 (10)
C70.141 (15)0.191 (17)0.075 (12)0.099 (12)0.016 (13)0.021 (14)
C80.126 (16)0.25 (3)0.120 (18)0.046 (12)0.031 (14)0.076 (18)
C90.097 (11)0.227 (19)0.075 (12)0.007 (12)0.014 (9)0.028 (13)
C100.103 (11)0.136 (13)0.075 (11)0.000 (10)0.008 (9)0.005 (10)
C110.033 (8)0.37 (4)0.071 (11)0.054 (16)0.018 (7)0.064 (19)
C120.16 (2)0.082 (16)0.21 (3)0.065 (15)0.10 (2)0.054 (16)
C130.090 (12)0.122 (14)0.090 (12)0.023 (11)0.015 (9)0.042 (10)
C140.078 (11)0.069 (11)0.109 (13)0.002 (9)0.034 (10)0.031 (10)
C150.048 (8)0.137 (14)0.094 (10)0.015 (8)0.029 (7)0.057 (10)
C160.107 (13)0.051 (10)0.23 (2)0.006 (9)0.102 (14)0.001 (11)
C170.077 (11)0.133 (15)0.099 (12)0.004 (10)0.018 (10)0.022 (12)
C180.069 (11)0.107 (13)0.102 (13)0.003 (9)0.002 (10)0.009 (10)
C190.082 (10)0.093 (12)0.091 (11)0.013 (9)0.006 (9)0.031 (9)
C200.103 (12)0.068 (10)0.081 (11)0.039 (9)0.009 (9)0.009 (8)
C210.096 (11)0.086 (12)0.080 (11)0.000 (9)0.051 (9)0.004 (9)
C220.142 (16)0.090 (14)0.118 (15)0.007 (12)0.077 (12)0.010 (11)
C230.167 (18)0.099 (13)0.108 (14)0.010 (12)0.057 (13)0.009 (11)
C250.094 (11)0.060 (9)0.153 (16)0.003 (8)0.041 (11)0.018 (9)
C290.084 (11)0.072 (10)0.132 (15)0.007 (9)0.049 (10)0.023 (10)
C310.042 (8)0.114 (14)0.072 (10)0.013 (9)0.009 (8)0.021 (10)
C320.036 (8)0.100 (13)0.087 (11)0.001 (8)0.003 (8)0.011 (10)
C330.054 (9)0.124 (15)0.066 (10)0.012 (9)0.016 (8)0.019 (10)
C340.088 (12)0.105 (13)0.101 (13)0.029 (11)0.007 (11)0.011 (11)
C350.055 (9)0.135 (16)0.073 (11)0.011 (10)0.003 (8)0.018 (11)
C360.055 (9)0.098 (12)0.059 (9)0.007 (8)0.006 (7)0.013 (9)
C370.066 (9)0.132 (14)0.058 (9)0.007 (10)0.004 (7)0.006 (9)
C380.070 (10)0.070 (10)0.058 (9)0.001 (8)0.016 (8)0.010 (8)
C390.061 (9)0.075 (10)0.058 (9)0.018 (8)0.020 (7)0.008 (8)
C400.036 (7)0.069 (9)0.061 (8)0.001 (7)0.012 (7)0.005 (7)
C410.070 (10)0.070 (11)0.091 (11)0.004 (8)0.038 (8)0.000 (9)
C420.084 (11)0.060 (10)0.112 (13)0.025 (9)0.025 (10)0.035 (10)
C430.057 (9)0.117 (16)0.065 (10)0.011 (10)0.020 (8)0.018 (10)
C440.041 (7)0.077 (9)0.083 (9)0.006 (7)0.021 (7)0.012 (8)
C450.031 (7)0.083 (10)0.068 (9)0.006 (7)0.001 (6)0.025 (8)
C460.047 (7)0.062 (9)0.048 (8)0.012 (7)0.004 (6)0.008 (7)
C470.056 (8)0.062 (9)0.066 (9)0.012 (7)0.000 (7)0.018 (7)
C480.065 (9)0.085 (12)0.063 (9)0.000 (9)0.001 (8)0.016 (9)
C490.082 (10)0.055 (9)0.088 (11)0.017 (8)0.010 (9)0.014 (9)
C500.068 (9)0.058 (10)0.090 (11)0.005 (8)0.001 (8)0.019 (8)
C510.090 (11)0.073 (10)0.068 (9)0.041 (9)0.022 (9)0.028 (8)
C520.076 (10)0.066 (10)0.048 (8)0.002 (9)0.020 (7)0.001 (7)
C530.076 (10)0.045 (8)0.066 (9)0.008 (8)0.033 (8)0.007 (7)
C540.061 (9)0.070 (11)0.089 (11)0.013 (8)0.036 (9)0.008 (9)
C550.069 (11)0.081 (12)0.092 (11)0.015 (9)0.039 (9)0.023 (9)
C560.094 (13)0.049 (9)0.140 (16)0.024 (10)0.013 (11)0.022 (10)
C570.118 (15)0.080 (13)0.104 (13)0.026 (12)0.064 (12)0.030 (11)
C580.045 (9)0.110 (12)0.098 (12)0.008 (9)0.012 (8)0.022 (10)
Geometric parameters (Å, º) top
O1—C311.38 (2)C13—C141.363 (10)
O1—C1A1.432 (11)C14—C151.356 (10)
O1—C1B1.441 (11)C15—C161.318 (9)
O2—C2B1.419 (11)C17—C181.50 (2)
O2—C31.424 (10)C19—C201.52 (2)
O2—C2A1.429 (11)C21—C221.47 (2)
O3—C51.405 (10)C23—C24A1.485 (11)
O3—C41.420 (10)C23—C24B1.570 (11)
O4—C141.379 (10)C25—C26B1.515 (11)
O4—C171.420 (10)C25—C26A1.529 (11)
O5—C181.39 (2)C27A—C28A1.530 (11)
O5—C191.43 (2)C27B—C28B1.531 (11)
O6—C461.392 (14)C29—C30B1.516 (12)
O6—C201.42 (2)C29—C30A1.550 (11)
O7—C391.39 (2)C31—C321.40 (2)
O7—C211.408 (15)C31—C361.38 (2)
O8—C221.412 (10)C32—C331.36 (2)
O8—C231.411 (9)C32—C581.51 (2)
O9A—C251.410 (10)C33—C341.37 (2)
O9A—C24A1.451 (11)C34—C351.41 (2)
O9B—C24B1.413 (11)C35—C361.33 (2)
O9B—C251.450 (10)C36—C371.53 (2)
O10A—C27A1.430 (11)C37—C381.54 (2)
O10A—C26A1.413 (11)C38—C391.38 (2)
O10B—C27B1.418 (11)C38—C431.40 (2)
O10B—C26B1.429 (12)C39—C401.38 (2)
O11—C28A1.414 (11)C40—C411.40 (2)
O11—C291.422 (10)C40—C441.50 (2)
O11—C28B1.431 (11)C41—C421.34 (2)
O12—C531.386 (14)C42—C431.39 (2)
O12—C30B1.428 (11)C44—C451.53 (2)
O12—C30A1.440 (11)C45—C501.37 (2)
N1—N21.08C45—C461.39 (2)
N1—C81.431 (14)C46—C471.36 (2)
N2—C111.358 (8)C47—C481.37 (2)
C1A—C2A1.529 (11)C47—C511.55 (2)
C1B—C2B1.529 (11)C48—C491.37 (2)
C3—C41.524 (10)C49—C501.38 (2)
C5—C101.392 (10)C51—C521.48 (2)
C5—C61.41 (2)C52—C531.39 (2)
C6—C71.423 (10)C52—C571.41 (2)
C7—C81.357 (11)C53—C541.40 (2)
C8—C91.364 (11)C54—C551.38 (2)
C9—C101.385 (10)C54—C581.51 (2)
C11—C121.381 (9)C55—C561.36 (2)
C11—C161.390 (9)C56—C571.37 (2)
C12—C131.335 (10)
C31—O1—C1A127.1 (16)O10A—C27A—C28A108.1 (10)
C31—O1—C1B97.6 (16)O10B—C27B—C28B108.3 (11)
C2B—O2—C3115.3 (19)O11—C28A—C27A106.5 (18)
C3—O2—C2A101.4 (14)O11—C28B—C27B102.4 (16)
C5—O3—C4117.1 (12)O11—C29—C30B109.8 (11)
C14—O4—C17116.4 (12)O11—C29—C30A106.0 (10)
C18—O5—C19113.8 (11)O12—C30A—C29107.0 (11)
C46—O6—C20112.6 (10)O12—C30B—C29109.4 (12)
C39—O7—C21115.2 (10)O1—C31—C32118.7 (16)
C22—O8—C23116.5 (12)O1—C31—C36119.3 (14)
C25—O9A—C24A103.8 (11)C32—C31—C36121.9 (17)
C24B—O9B—C25129 (3)C33—C32—C31117.7 (15)
C27A—O10A—C26A119 (2)C33—C32—C58117.7 (15)
C27B—O10B—C26B112 (2)C31—C32—C58124.2 (17)
C28A—O11—C29113.7 (17)C32—C33—C34120.9 (15)
C29—O11—C28B111.9 (13)C33—C34—C35119.7 (17)
C53—O12—C30B114.9 (8)C36—C35—C34120.7 (17)
C53—O12—C30A114.8 (8)C35—C36—C31118.8 (15)
N2—N1—C8130.6 (6)C35—C36—C37122.1 (14)
N1—N2—C11147.2 (6)C31—C36—C37119.0 (16)
O1—C1A—C2A106.3 (18)C36—C37—C38110.0 (11)
O1—C1B—C2B112 (2)C39—C38—C43118.4 (14)
O2—C2A—C1A107.6 (18)C39—C38—C37124.2 (14)
O2—C2B—C1B105 (2)C43—C38—C37117.3 (15)
O2—C3—C4105.4 (12)C38—C39—C40122.0 (13)
O3—C4—C3109.6 (13)C38—C39—O7118.3 (14)
C10—C5—C6117.7 (13)C40—C39—O7119.7 (12)
C10—C5—O3109.0 (12)C39—C40—C41118.0 (13)
C6—C5—O3133.3 (14)C39—C40—C44120.1 (12)
C5—C6—C7116.0 (16)C41—C40—C44121.3 (13)
C8—C7—C6129.4 (18)C42—C41—C40120.8 (15)
C9—C8—C7109.3 (18)C41—C42—C43121.3 (15)
C9—C8—N1117.3 (11)C42—C43—C38119.1 (14)
C7—C8—N1131.6 (14)C40—C44—C45110.1 (9)
C8—C9—C10128.6 (19)C50—C45—C46117.4 (12)
C5—C10—C9118.8 (17)C50—C45—C44121.5 (13)
N2—C11—C12123.2 (9)C46—C45—C44120.9 (12)
N2—C11—C16113.2 (9)C47—C46—C45122.4 (12)
C12—C11—C16123.6 (9)C47—C46—O6120.1 (11)
C11—C12—C13119.1 (13)C45—C46—O6117.5 (11)
C12—C13—C14111.6 (14)C48—C47—C46118.9 (13)
C15—C14—C13133.8 (14)C48—C47—C51118.6 (12)
C15—C14—O4107.7 (12)C46—C47—C51121.2 (12)
C13—C14—O4118.5 (13)C47—C48—C49120.3 (14)
C14—C15—C16112.1 (13)C50—C49—C48119.7 (13)
C15—C16—C11119.5 (11)C45—C50—C49120.8 (14)
O4—C17—C18108.0 (13)C52—C51—C47114.3 (11)
O5—C18—C17109.6 (13)C53—C52—C57117.2 (16)
O5—C19—C20115.6 (12)C53—C52—C51120.1 (13)
O6—C20—C19110.4 (12)C57—C52—C51122.4 (16)
O7—C21—C22109.9 (12)C52—C53—O12120.3 (13)
O8—C22—C21114.1 (14)C52—C53—C54122.1 (13)
O8—C23—C24A114.8 (9)O12—C53—C54117.6 (14)
O8—C23—C24B103.5 (9)C55—C54—C53117.0 (15)
O9A—C24A—C23105.8 (10)C55—C54—C58122.0 (16)
O9B—C24B—C23109.8 (11)C53—C54—C58120.6 (13)
O9B—C25—C26B107.0 (19)C56—C55—C54123.2 (16)
O9A—C25—C26A102.0 (13)C55—C56—C57118.9 (15)
O10A—C26A—C25110.3 (11)C56—C57—C52121.5 (17)
O10B—C26B—C25107.9 (11)C54—C58—C32109.3 (11)
(2a) top
Crystal data top
C58H64N2O12F(000) = 2088
Mr = 981.11Dx = 1.239 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 20.341 (6) ÅCell parameters from 25 reflections
b = 11.709 (3) Åθ = 8–12°
c = 23.875 (8) ŵ = 0.09 mm1
β = 112.39 (2)°T = 273 K
V = 5258 (3) Å3Parallelepipedic, orange
Z = 40.65 × 0.60 × 0.50 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 23°, θmin = 1°
Graphite monochromatorh = 022
ω/θ scansk = 012
7559 measured reflectionsl = 2624
7304 independent reflections3 standard reflections every 60 min
3495 reflections with I > 2σ(I) intensity decay: 0.4%
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)] = 0.107Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.367H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1516P)2 + 13.1365P],
where P = (Fo2 + 2Fc2)/3
5696 reflections(Δ/σ)max = 0.016
636 parametersΔρmax = 0.56 e Å3
75 restraintsΔρmin = 0.33 e Å3
Crystal data top
C58H64N2O12V = 5258 (3) Å3
Mr = 981.11Z = 4
Monoclinic, P21/aMo Kα radiation
a = 20.341 (6) ŵ = 0.09 mm1
b = 11.709 (3) ÅT = 273 K
c = 23.875 (8) Å0.65 × 0.60 × 0.50 mm
β = 112.39 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.017
7559 measured reflectionsθmax = 23°
7304 independent reflections3 standard reflections every 60 min
3495 reflections with I > 2σ(I) intensity decay: 0.4%
Refinement top
R[F2 > 2σ(F2)] = 0.10775 restraints
wR(F2) = 0.367H-atom parameters constrained
S = 1.07Δρmax = 0.56 e Å3
5696 reflectionsΔρmin = 0.33 e Å3
636 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. All atoms refined anisotropically, unless those of the disordered parts of the molecule that were refined isotropically, with occupation factors constrained to sum to unity. The occupation factors have been constrained to be equal for atoms in the same fragment of disordered parts. The low data quality resulted in some non physical bond lengths and angles in the disordered parts of the molecule, hence those bond lengths were restrained to the usual values: O—C 1.426 (10) A, N-Car. 1.43 (1) A and C—C 1.53 (1) A. Some 1···3 distances were also restrained (C···O 2.39 (1), C···C 2.36 (1) A) so as to restrain the bond angles around O(3), O(8), O(10 A), O(10B), O(11 A), O(11B), C(24 A), C(24B), C(26) and C(27). C(28 A) and C(28B), being unstable on refinement, have been given fixed occupations (1/2) and isotropic displacement factors (0.15). Hydrogen atoms were introduced, unless for the disordered parts, at calculated positions and constrained to ride on their parent carbon atoms (C—H 0.97 A for CH2, 0.93 A for Car·H, displacement factor equal to 1.2 times that of the parent carbon atom). Refinement on F2 for all reflections except those with very negative F2 or flagged for rejection. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3167 (3)0.0297 (6)0.2072 (4)0.091 (2)
O2A0.4558 (7)0.1238 (14)0.2473 (6)0.106 (6)*0.60 (2)
O2B0.4626 (6)0.2055 (14)0.2264 (6)0.071 (7)*0.41 (2)
O30.5656 (4)0.1722 (9)0.3615 (3)0.123 (3)
O40.0827 (3)0.0301 (7)0.4923 (3)0.082 (2)
O50.0782 (3)0.1844 (7)0.3959 (3)0.081 (2)
O60.1708 (3)0.2595 (6)0.3354 (3)0.075 (2)
O70.0690 (3)0.0999 (6)0.1302 (3)0.076 (2)
O80.0186 (6)0.1624 (8)0.0068 (4)0.147 (4)
O9A0.0927 (8)0.3541 (13)0.0315 (8)0.151 (7)*0.70 (2)
O9B0.0734 (15)0.421 (2)0.0017 (11)0.132 (9)*0.31 (2)
O10A0.1970 (9)0.5125 (17)0.0310 (11)0.163 (14)*0.66 (3)
O10B0.2089 (10)0.5104 (18)0.0159 (5)0.158 (15)*0.35 (3)
O11A0.3324 (10)0.5120 (14)0.1411 (4)0.168 (15)*0.66 (3)
O11B0.3068 (9)0.5984 (12)0.1668 (6)0.145 (16)*0.35 (3)
O120.3240 (4)0.3892 (6)0.2354 (3)0.076 (2)
N10.3329 (4)0.1618 (7)0.4297 (3)0.060 (2)
N20.3332 (4)0.0801 (7)0.4636 (3)0.059 (2)
C1A0.3349 (7)0.1239 (17)0.1763 (10)0.120 (11)*0.60 (2)
C1B0.3456 (8)0.1352 (13)0.1990 (14)0.068 (9)*0.41 (2)
C2A0.4124 (7)0.114 (3)0.1848 (7)0.16 (2)*0.60 (2)
C2B0.4208 (12)0.110 (2)0.2004 (18)0.14 (2)*0.41 (2)
C3A0.5302 (7)0.131 (2)0.2565 (6)0.113 (9)*0.60 (2)
C3B0.5366 (8)0.184 (2)0.2539 (5)0.081 (9)*0.41 (2)
C4A0.5631 (9)0.2196 (19)0.3074 (6)0.159 (8)*0.60 (2)
C4B0.5655 (10)0.2481 (19)0.3148 (6)0.154 (10)*0.41 (2)
C50.5084 (6)0.1825 (10)0.3780 (5)0.075 (3)
C60.4487 (7)0.2472 (11)0.3525 (6)0.097 (4)
H60.4455 (7)0.2959 (11)0.3208 (6)0.116*
C70.3933 (6)0.2435 (11)0.3715 (5)0.084 (3)
H70.3538 (6)0.2897 (11)0.3528 (5)0.101*
C80.3954 (5)0.1734 (8)0.4172 (5)0.061 (2)
C90.4561 (5)0.1101 (10)0.4454 (5)0.084 (3)
H90.4587 (5)0.0620 (10)0.4772 (5)0.101*
C100.5123 (6)0.1158 (10)0.4282 (6)0.083 (3)
H100.5536 (6)0.0754 (10)0.4496 (6)0.100*
C110.2680 (4)0.0635 (8)0.4719 (4)0.053 (2)
C120.2108 (5)0.1335 (8)0.4503 (4)0.059 (2)
H120.2129 (5)0.2013 (8)0.4308 (4)0.070*
C130.1491 (5)0.1021 (10)0.4580 (4)0.071 (3)
H130.1100 (5)0.1505 (10)0.4439 (4)0.085*
C140.1441 (5)0.0019 (10)0.4855 (4)0.062 (3)
C150.2037 (5)0.0654 (10)0.5100 (4)0.071 (3)
H150.2020 (5)0.1311 (10)0.5313 (4)0.086*
C160.2655 (4)0.0368 (8)0.5035 (4)0.062 (2)
H160.3054 (4)0.0830 (8)0.5197 (4)0.075*
C170.0241 (5)0.0472 (11)0.4367 (6)0.101 (4)
H17A0.0197 (5)0.0286 (11)0.4420 (6)0.121*
H17B0.0283 (5)0.0038 (11)0.4062 (6)0.121*
C180.0205 (5)0.1690 (11)0.4150 (5)0.091 (4)
H18A0.0243 (5)0.1829 (11)0.3816 (5)0.109*
H18B0.0246 (5)0.2216 (11)0.4475 (5)0.109*
C190.0875 (5)0.3014 (12)0.3845 (5)0.086 (3)
H19A0.0811 (5)0.3487 (12)0.4154 (5)0.103*
H19B0.0522 (5)0.3236 (12)0.3455 (5)0.103*
C200.1610 (5)0.3194 (12)0.3848 (5)0.098 (4)
H20A0.1689 (5)0.4005 (12)0.3815 (5)0.118*
H20B0.1960 (5)0.2927 (12)0.4230 (5)0.118*
C210.0046 (6)0.0458 (12)0.0931 (5)0.105 (5)
H21A0.0185 (6)0.0133 (12)0.1182 (5)0.126*
H21B0.0148 (6)0.0157 (12)0.0704 (5)0.126*
C220.0442 (6)0.1322 (12)0.0498 (6)0.141 (7)
H22A0.0913 (6)0.0997 (12)0.0305 (6)0.169*
H22B0.0479 (6)0.1995 (12)0.0721 (6)0.169*
C23A0.0147 (17)0.2701 (19)0.0122 (11)0.179 (11)*0.70 (2)
C23B0.0385 (11)0.241 (2)0.0258 (13)0.164 (14)*0.31 (2)
C24A0.0270 (12)0.2939 (18)0.0464 (8)0.159 (11)*0.70 (2)
C24B0.0148 (12)0.344 (2)0.0179 (19)0.176 (12)*0.31 (2)
C250.0855 (7)0.4674 (13)0.0481 (8)0.214 (8)
C260.1466 (8)0.5424 (14)0.0285 (7)0.224 (9)
C270.2395 (5)0.6023 (12)0.0604 (4)0.292 (16)
C28A0.31830.58260.08970.150*0.50
C28B0.25760.53430.12080.150*0.50
C290.3737 (6)0.5546 (13)0.1965 (4)0.206 (11)
C300.3779 (7)0.4741 (10)0.2474 (4)0.126 (5)
H30A0.4235 (7)0.4354 (10)0.2605 (4)0.151*
H30B0.3777 (7)0.5199 (10)0.2812 (4)0.151*
C310.2842 (5)0.0512 (8)0.1631 (4)0.061 (2)
C320.2170 (5)0.0314 (9)0.1213 (4)0.067 (3)
C330.1877 (7)0.1134 (12)0.0763 (5)0.088 (3)
H330.1427 (7)0.1025 (12)0.0465 (5)0.105*
C340.2261 (9)0.2118 (13)0.0763 (6)0.108 (5)
H340.2083 (9)0.2632 (13)0.0443 (6)0.130*
C350.2876 (7)0.2334 (11)0.1211 (6)0.087 (3)
H350.3092 (7)0.3039 (11)0.1224 (6)0.105*
C360.3204 (6)0.1552 (10)0.1657 (5)0.079 (3)
C370.3863 (5)0.1821 (10)0.2209 (5)0.085 (3)
H37A0.4100 (5)0.2476 (10)0.2122 (5)0.102*
H37B0.4186 (5)0.1177 (10)0.2295 (5)0.102*
C380.3698 (5)0.2078 (10)0.2769 (5)0.071 (3)
C390.3377 (5)0.3079 (10)0.2805 (5)0.068 (3)
C400.3158 (5)0.3278 (10)0.3282 (5)0.073 (3)
C410.3306 (6)0.2453 (13)0.3733 (5)0.086 (4)
H410.3171 (6)0.2569 (13)0.4059 (5)0.103*
C420.3648 (6)0.1487 (14)0.3697 (7)0.100 (4)
H420.3759 (6)0.0955 (14)0.4008 (7)0.120*
C430.3827 (6)0.1277 (11)0.3232 (6)0.087 (3)
H430.4043 (6)0.0586 (11)0.3212 (6)0.104*
C440.2687 (6)0.4296 (10)0.3267 (5)0.084 (3)
H44A0.2893 (6)0.4986 (10)0.3179 (5)0.101*
H44B0.2655 (6)0.4386 (10)0.3660 (5)0.101*
C450.1947 (6)0.4117 (10)0.2785 (5)0.071 (3)
C460.1509 (5)0.3218 (9)0.2822 (4)0.066 (3)
C470.0911 (5)0.2884 (9)0.2332 (4)0.064 (3)
C480.0707 (6)0.3515 (12)0.1818 (5)0.082 (3)
H480.0300 (6)0.3306 (12)0.1490 (5)0.098*
C490.1081 (8)0.4443 (12)0.1768 (6)0.095 (4)
H490.0916 (8)0.4885 (12)0.1418 (6)0.114*
C500.1715 (7)0.4733 (11)0.2246 (7)0.092 (4)
H500.1984 (7)0.5343 (11)0.2202 (7)0.111*
C510.0543 (5)0.1772 (11)0.2360 (5)0.081 (3)
H51A0.0429 (5)0.1775 (11)0.2719 (5)0.097*
H51B0.0099 (5)0.1727 (11)0.2010 (5)0.097*
C520.0979 (5)0.0730 (10)0.2372 (5)0.067 (3)
C530.1070 (5)0.0405 (9)0.1838 (5)0.068 (3)
C540.1533 (5)0.0470 (9)0.1822 (5)0.068 (3)
C550.1882 (6)0.1023 (10)0.2363 (6)0.087 (3)
H550.2197 (6)0.1609 (10)0.2376 (6)0.104*
C560.1783 (8)0.0744 (12)0.2879 (6)0.102 (4)
H560.2007 (8)0.1172 (12)0.3228 (6)0.122*
C570.1362 (6)0.0151 (12)0.2892 (5)0.084 (3)
H570.1334 (6)0.0370 (12)0.3257 (5)0.101*
C580.1720 (5)0.0689 (9)0.1279 (5)0.078 (3)
H58A0.1291 (5)0.0757 (9)0.0918 (5)0.094*
H58B0.1986 (5)0.1395 (9)0.1333 (5)0.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.069 (4)0.069 (5)0.115 (6)0.000 (4)0.012 (4)0.018 (5)
O30.060 (5)0.206 (10)0.102 (6)0.032 (6)0.032 (4)0.024 (6)
O40.050 (4)0.134 (7)0.063 (4)0.004 (4)0.025 (3)0.010 (4)
O50.065 (4)0.109 (6)0.086 (5)0.011 (4)0.049 (4)0.018 (4)
O60.071 (4)0.104 (6)0.050 (4)0.029 (4)0.023 (3)0.009 (4)
O70.054 (4)0.096 (5)0.063 (4)0.006 (4)0.006 (3)0.010 (4)
O80.172 (11)0.137 (9)0.089 (6)0.015 (8)0.000 (7)0.006 (7)
O120.080 (5)0.057 (4)0.093 (5)0.021 (4)0.037 (4)0.003 (4)
N10.057 (5)0.057 (5)0.063 (5)0.001 (4)0.020 (4)0.006 (4)
N20.055 (5)0.056 (5)0.057 (5)0.006 (4)0.012 (4)0.009 (4)
C50.065 (7)0.096 (9)0.074 (7)0.027 (6)0.036 (6)0.025 (7)
C60.100 (9)0.102 (10)0.107 (9)0.013 (8)0.061 (8)0.016 (8)
C70.070 (7)0.103 (9)0.085 (8)0.015 (6)0.036 (6)0.024 (7)
C80.050 (6)0.058 (6)0.075 (6)0.007 (5)0.022 (5)0.005 (5)
C90.054 (6)0.102 (9)0.100 (8)0.016 (6)0.033 (6)0.034 (7)
C100.063 (6)0.082 (8)0.111 (9)0.001 (6)0.041 (6)0.004 (7)
C110.042 (5)0.065 (6)0.051 (5)0.002 (4)0.016 (4)0.003 (5)
C120.052 (5)0.060 (6)0.059 (6)0.010 (5)0.015 (4)0.000 (5)
C130.053 (6)0.090 (8)0.070 (6)0.022 (6)0.023 (5)0.000 (6)
C140.052 (6)0.081 (8)0.050 (5)0.004 (5)0.017 (5)0.013 (5)
C150.058 (6)0.089 (8)0.074 (6)0.009 (6)0.033 (5)0.002 (6)
C160.044 (5)0.066 (7)0.074 (6)0.004 (5)0.020 (5)0.013 (5)
C170.043 (6)0.152 (13)0.119 (10)0.005 (7)0.044 (7)0.035 (9)
C180.058 (6)0.149 (12)0.065 (7)0.005 (7)0.025 (5)0.011 (8)
C190.091 (8)0.114 (11)0.061 (6)0.001 (7)0.038 (6)0.011 (7)
C200.085 (8)0.148 (12)0.067 (7)0.043 (8)0.036 (6)0.023 (8)
C210.064 (7)0.180 (14)0.063 (7)0.011 (8)0.017 (6)0.032 (8)
C220.083 (9)0.218 (19)0.073 (9)0.020 (11)0.025 (8)0.045 (11)
C250.177 (17)0.174 (18)0.29 (2)0.020 (12)0.085 (17)0.047 (16)
C260.158 (17)0.193 (18)0.30 (2)0.025 (13)0.070 (18)0.040 (17)
C270.41 (4)0.34 (4)0.17 (2)0.07 (4)0.16 (3)0.10 (3)
C290.28 (3)0.074 (10)0.37 (3)0.059 (14)0.24 (3)0.007 (16)
C300.132 (12)0.091 (10)0.183 (15)0.074 (9)0.093 (11)0.046 (10)
C310.056 (6)0.059 (6)0.064 (6)0.012 (5)0.017 (5)0.011 (5)
C320.068 (6)0.073 (7)0.061 (6)0.010 (6)0.025 (5)0.009 (6)
C330.096 (8)0.107 (10)0.060 (7)0.025 (8)0.030 (6)0.000 (7)
C340.148 (14)0.105 (11)0.076 (9)0.029 (10)0.047 (10)0.039 (8)
C350.101 (9)0.077 (8)0.086 (8)0.008 (7)0.037 (8)0.024 (7)
C360.083 (7)0.075 (8)0.097 (8)0.001 (7)0.055 (7)0.011 (7)
C370.058 (6)0.077 (8)0.114 (9)0.019 (6)0.026 (6)0.009 (7)
C380.051 (6)0.075 (8)0.080 (7)0.018 (5)0.016 (5)0.001 (6)
C390.051 (6)0.064 (7)0.079 (7)0.026 (5)0.014 (5)0.003 (6)
C400.056 (6)0.083 (8)0.079 (7)0.029 (6)0.023 (5)0.000 (7)
C410.060 (7)0.124 (11)0.061 (7)0.015 (7)0.009 (5)0.000 (8)
C420.061 (7)0.122 (13)0.097 (10)0.020 (8)0.007 (7)0.022 (9)
C430.059 (7)0.092 (9)0.091 (8)0.003 (6)0.007 (6)0.020 (8)
C440.081 (7)0.087 (8)0.084 (7)0.024 (7)0.031 (6)0.015 (6)
C450.078 (7)0.082 (8)0.067 (7)0.004 (6)0.044 (6)0.010 (6)
C460.069 (6)0.086 (8)0.050 (6)0.009 (6)0.031 (5)0.001 (6)
C470.058 (6)0.078 (7)0.055 (6)0.005 (5)0.021 (5)0.015 (5)
C480.067 (7)0.116 (10)0.052 (6)0.017 (7)0.010 (5)0.000 (7)
C490.112 (10)0.097 (10)0.073 (8)0.023 (9)0.031 (8)0.014 (7)
C500.090 (9)0.084 (9)0.121 (11)0.009 (7)0.061 (9)0.000 (8)
C510.045 (5)0.129 (10)0.060 (6)0.011 (7)0.011 (5)0.021 (7)
C520.051 (5)0.089 (8)0.063 (6)0.025 (5)0.023 (5)0.025 (6)
C530.041 (5)0.077 (7)0.073 (7)0.014 (5)0.008 (5)0.004 (6)
C540.059 (6)0.068 (7)0.068 (7)0.016 (5)0.014 (5)0.009 (6)
C550.087 (8)0.071 (8)0.096 (9)0.006 (6)0.027 (7)0.010 (7)
C560.123 (11)0.089 (10)0.092 (10)0.014 (9)0.039 (8)0.037 (8)
C570.079 (7)0.103 (10)0.068 (8)0.021 (7)0.026 (6)0.013 (7)
C580.057 (6)0.081 (8)0.086 (7)0.010 (5)0.016 (5)0.029 (6)
Geometric parameters (Å, º) top
O1—C311.382 (11)C11—C121.354 (12)
O1—C1B1.414 (10)C11—C161.407 (12)
O1—C1A1.452 (10)C12—C131.384 (13)
O2A—C2A1.420 (10)C13—C141.367 (14)
O2A—C3A1.445 (10)C14—C151.376 (14)
O2B—C2B1.399 (10)C15—C161.365 (12)
O2B—C3B1.416 (10)C17—C181.510 (9)
O3—C51.369 (11)C19—C201.508 (9)
O3—C4A1.388 (10)C21—C221.515 (10)
O3—C4B1.426 (10)C23A—C24A1.538 (10)
O4—C141.372 (11)C23B—C24B1.544 (11)
O4—C171.421 (13)C25—C261.446 (8)
O5—C181.422 (11)C27—C28A1.502 (10)
O5—C191.423 (13)C27—C28B1.563 (9)
O6—C461.383 (11)C29—C301.515 (9)
O6—C201.450 (12)C31—C321.372 (13)
O7—C531.400 (12)C31—C361.412 (14)
O7—C211.422 (12)C32—C331.394 (15)
O8—C221.364 (13)C32—C581.532 (14)
O8—C23A1.414 (10)C33—C341.39 (2)
O8—C23B1.413 (11)C34—C351.33 (2)
O9A—C251.377 (10)C35—C361.37 (2)
O9A—C24A1.430 (10)C36—C371.513 (15)
O9B—C251.414 (10)C37—C381.53 (2)
O9B—C24B1.426 (11)C38—C391.360 (15)
O10A—C271.372 (10)C38—C431.397 (15)
O10A—C261.444 (10)C39—C401.391 (15)
O10B—C261.359 (10)C40—C411.39 (2)
O10B—C271.473 (11)C40—C441.52 (2)
O11A—C291.364 (10)C41—C421.35 (2)
O11A—C28A1.414 (9)C42—C431.32 (2)
O11B—C291.373 (10)C44—C451.521 (15)
O11B—C28B1.390 (10)C45—C501.39 (2)
O12—C391.385 (12)C45—C461.404 (14)
O12—C301.427 (12)C46—C471.384 (13)
N1—N21.251 (10)C47—C481.356 (15)
N1—C81.419 (11)C47—C511.516 (14)
N2—C111.427 (11)C48—C491.36 (2)
C1A—C2A1.515 (10)C49—C501.40 (2)
C1B—C2B1.546 (10)C51—C521.502 (15)
C3A—C4A1.543 (10)C52—C571.368 (15)
C3B—C4B1.539 (10)C52—C531.410 (13)
C5—C61.36 (2)C53—C541.402 (14)
C5—C101.407 (15)C54—C551.375 (15)
C6—C71.366 (15)C54—C581.505 (14)
C7—C81.354 (14)C55—C561.36 (2)
C8—C91.377 (14)C56—C571.36 (2)
C9—C101.354 (14)
C31—O1—C1B126.6 (15)O10B—C26—C25121.0 (11)
C31—O1—C1A105.9 (12)O10A—C26—C25111.8 (8)
C2A—O2A—C3A111.1 (9)O10A—C27—C28A118.3 (12)
C2B—O2B—C3B115.1 (11)O10B—C27—C28B100.4 (9)
C5—O3—C4A119.9 (11)O11A—C28A—C27108.8 (8)
C5—O3—C4B115.0 (11)O11B—C28B—C27107.4 (7)
C14—O4—C17114.0 (7)O11B—C29—C30112.8 (9)
C18—O5—C19111.6 (8)O11A—C29—C30112.1 (8)
C46—O6—C20114.1 (9)O12—C30—C29117.9 (8)
C53—O7—C21113.8 (8)C32—C31—O1119.5 (9)
C22—O8—C23A118.0 (10)C32—C31—C36122.4 (10)
C22—O8—C23B115.4 (14)O1—C31—C36117.9 (9)
C25—O9A—C24A114.7 (11)C31—C32—C33117.3 (10)
C25—O9B—C24B111.1 (12)C31—C32—C58121.6 (9)
C27—O10A—C26113.0 (12)C33—C32—C58120.7 (10)
C26—O10B—C27112.0 (12)C32—C33—C34119.7 (11)
C29—O11A—C28A118.3 (12)C35—C34—C33120.9 (12)
C29—O11B—C28B118.7 (11)C34—C35—C36122.1 (13)
C39—O12—C30114.3 (7)C35—C36—C31116.9 (11)
N2—N1—C8115.1 (8)C35—C36—C37123.1 (11)
N1—N2—C11114.7 (7)C31—C36—C37119.4 (11)
O1—C1A—C2A109.2 (10)C36—C37—C38112.8 (8)
O1—C1B—C2B106.9 (10)C39—C38—C43118.6 (11)
O2A—C2A—C1A109.5 (10)C39—C38—C37119.7 (10)
O2B—C2B—C1B106.6 (10)C43—C38—C37121.5 (12)
O2A—C3A—C4A105.9 (9)C38—C39—C40120.5 (11)
O2B—C3B—C4B108.0 (10)C38—C39—O12120.1 (10)
O3—C4A—C3A108.4 (10)C40—C39—O12119.3 (11)
O3—C4B—C3B108.8 (11)C39—C40—C41118.3 (12)
O3—C5—C6129.1 (10)C39—C40—C44120.5 (11)
O3—C5—C10114.7 (11)C41—C40—C44120.7 (11)
C6—C5—C10116.2 (9)C42—C41—C40119.9 (12)
C5—C6—C7122.8 (11)C43—C42—C41121.8 (14)
C8—C7—C6120.7 (11)C42—C43—C38120.8 (13)
C7—C8—C9117.9 (9)C40—C44—C45110.0 (9)
C7—C8—N1118.2 (9)C50—C45—C46116.6 (10)
C9—C8—N1123.7 (9)C50—C45—C44121.2 (10)
C10—C9—C8121.9 (10)C46—C45—C44121.6 (10)
C9—C10—C5120.4 (11)O6—C46—C47118.8 (10)
C12—C11—C16120.5 (8)O6—C46—C45118.8 (9)
C12—C11—N2125.1 (9)C47—C46—C45122.2 (9)
C16—C11—N2114.4 (8)C48—C47—C46118.6 (11)
C11—C12—C13118.7 (9)C48—C47—C51121.4 (10)
C14—C13—C12121.9 (9)C46—C47—C51119.8 (9)
C13—C14—O4121.9 (9)C47—C48—C49121.9 (11)
C13—C14—C15118.8 (9)C48—C49—C50119.7 (12)
O4—C14—C15119.2 (10)C45—C50—C49120.7 (12)
C16—C15—C14120.7 (10)C52—C51—C47113.6 (8)
C15—C16—C11119.3 (9)C57—C52—C53117.5 (11)
O4—C17—C18111.5 (10)C57—C52—C51123.3 (10)
O5—C18—C17107.0 (9)C53—C52—C51118.7 (10)
O5—C19—C20109.7 (10)C54—C53—C52122.8 (10)
O6—C20—C19111.9 (8)C54—C53—O7118.8 (9)
O7—C21—C22109.6 (10)C52—C53—O7118.4 (9)
O8—C22—C21110.4 (12)C55—C54—C53115.6 (10)
O8—C23A—C24A108.4 (10)C55—C54—C58121.2 (11)
O8—C23B—C24B106.4 (11)C53—C54—C58122.7 (10)
O9A—C24A—C23A108.7 (10)C56—C55—C54122.3 (12)
O9B—C24B—C23B105.4 (11)C55—C56—C57121.1 (12)
O9A—C25—C26120.6 (10)C52—C57—C56120.4 (12)
O9B—C25—C26111.5 (9)C54—C58—C32108.4 (8)
(2b) top
Crystal data top
C58H64N2O12Z = 4
Mr = 981.11F(000) = 2088
Triclinic, P1Dx = 1.253 Mg m3
a = 20.285 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.608 (4) ÅCell parameters from 25 reflections
c = 23.894 (6) Åθ = 8–12°
α = 92.22 (3)°µ = 0.09 mm1
β = 112.32 (2)°T = 213 K
γ = 87.81 (3)°Parallelepipedic, orange
V = 5199 (3) Å30.65 × 0.60 × 0.50 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 23°, θmin = 1°
Graphite monochromatorh = 2222
w/2θ scansk = 012
13177 measured reflectionsl = 2626
12513 independent reflections3 standard reflections every 60 min
8852 reflections with I > 2σ(I) intensity decay: 5.6%
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)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.1351P)2 + 11.9644P],
where P = (Fo2 + 2Fc2)/3
12460 reflections(Δ/σ)max = 0.019
1290 parametersΔρmax = 0.66 e Å3
104 restraintsΔρmin = 0.50 e Å3
Crystal data top
C58H64N2O12γ = 87.81 (3)°
Mr = 981.11V = 5199 (3) Å3
Triclinic, P1Z = 4
a = 20.285 (8) ÅMo Kα radiation
b = 11.608 (4) ŵ = 0.09 mm1
c = 23.894 (6) ÅT = 213 K
α = 92.22 (3)°0.65 × 0.60 × 0.50 mm
β = 112.32 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.021
13177 measured reflectionsθmax = 23°
12513 independent reflections3 standard reflections every 60 min
8852 reflections with I > 2σ(I) intensity decay: 5.6%
Refinement top
R[F2 > 2σ(F2)] = 0.080104 restraints
wR(F2) = 0.245H-atom parameters constrained
S = 0.97Δρmax = 0.66 e Å3
12460 reflectionsΔρmin = 0.50 e Å3
1290 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. All atoms refined anisotropically, unless those of the disordered parts of the molecule that were refined isotropically, with occupation factors constrained to sum to unity. The occupation factors have been constrained to be equal for atoms in the same fragment of disordered parts. The low data quality resulted in some non physical bond lengths and angles in the disordered parts of the molecule, hence those bond lengths were restrained to the usual values: O—C 1.426 (10) A, N-Car. 1.43 (1) A and C—C 1.53 (1) A; some 1···3 distances were also restrained (C···O 2.39 (1), C···C 2.36 (1) A) so as to restrain the bond angles around O(3 A), O(8i), O(8j), O(9i), O(9j), C(22i), C(22j), C(23i), C(23j), C(24i), C(24j), C(25 A) for molecule A and O(8B), O(9k), O(9 l), O(10k), O(10 l), O(11k), O(11 l), C(23B), C(24k), C(24 l), C(26k), C(26 l), C(27k), C(27 l), C(28k), C(28 l) for molecule B. Hydrogen atoms were introduced, unless for the disordered parts, at calculated positions and constrained to ride on their parent carbon atoms (C—H 0.97 A for CH2, 0.93 A for Car·H, displacement factor equal to 1.2 times that of the parent carbon atom). Refinement on F2 for all reflections except those with very negative F2 or flagged for rejection. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.6766 (2)0.2402 (3)0.3401 (2)0.0503 (10)
O2A0.5797 (2)0.1675 (4)0.3966 (2)0.0634 (11)
O3A0.5821 (2)0.0195 (4)0.4933 (2)0.0592 (11)
O4A1.0698 (2)0.1506 (4)0.3628 (2)0.0601 (11)
O5A0.9616 (2)0.1535 (4)0.2332 (2)0.0616 (11)
O6A0.8209 (2)0.0406 (3)0.1889 (2)0.0483 (9)
O7A0.5699 (2)0.0950 (4)0.1301 (2)0.0717 (14)
O8I0.5033 (5)0.1802 (8)0.0016 (4)0.063 (3)*0.470 (7)
O8J0.4803 (4)0.1603 (5)0.0172 (3)0.045 (2)*0.545 (7)
O9I0.5764 (4)0.3189 (7)0.0551 (5)0.080 (3)*0.470 (7)
O9J0.5495 (4)0.3515 (7)0.0243 (4)0.082 (3)*0.545 (7)
O10A0.6621 (3)0.5072 (4)0.0271 (2)0.0681 (12)
O11A0.8265 (3)0.5504 (4)0.1511 (2)0.0794 (14)
O12A0.8221 (2)0.3878 (3)0.2396 (2)0.0414 (8)
N1A0.8382 (2)0.0867 (4)0.4668 (2)0.0415 (10)
N2A0.8388 (2)0.1685 (4)0.4311 (2)0.0444 (11)
C1A0.6654 (3)0.2951 (6)0.3908 (3)0.063 (2)
H1A10.6752 (3)0.3764 (6)0.3918 (3)0.076*
H1A20.6992 (3)0.2623 (6)0.4277 (3)0.076*
C2A0.5920 (3)0.2831 (6)0.3896 (3)0.064 (2)
H2A10.5863 (3)0.3302 (6)0.4219 (3)0.077*
H2A20.5574 (3)0.3101 (6)0.3514 (3)0.077*
C3A0.5194 (3)0.1556 (6)0.4126 (3)0.075 (2)
C4I0.5534 (12)0.1306 (15)0.4792 (6)0.064 (18)*0.14 (2)
C4J0.5230 (3)0.0375 (6)0.4363 (3)0.068 (3)*0.87 (2)
C5A0.6450 (2)0.0113 (5)0.4878 (2)0.0452 (14)
C6A0.6514 (3)0.1115 (5)0.4575 (3)0.0509 (14)
H6A0.6129 (3)0.1602 (5)0.4418 (3)0.061*
C7A0.7140 (3)0.1409 (5)0.4500 (2)0.0472 (14)
H7A0.7173 (3)0.2079 (5)0.4285 (2)0.057*
C8A0.7721 (3)0.0696 (5)0.4749 (2)0.0413 (13)
C9A0.7669 (3)0.0274 (5)0.5084 (2)0.0476 (14)
H9A0.8066 (3)0.0729 (5)0.5269 (2)0.057*
C10A0.7032 (3)0.0580 (5)0.5151 (2)0.0467 (13)
H10A0.6999 (3)0.1238 (5)0.5374 (2)0.056*
C11A0.9023 (3)0.1764 (4)0.4190 (2)0.0411 (12)
C12A0.9654 (3)0.1236 (5)0.4548 (2)0.0441 (13)
H12A0.9699 (3)0.0901 (5)0.4920 (2)0.053*
C13A1.0208 (3)0.1207 (5)0.4357 (2)0.0458 (13)
H13A1.0631 (3)0.0861 (5)0.4601 (2)0.055*
C14A1.0139 (3)0.1691 (5)0.3801 (3)0.0463 (13)
C15A0.9539 (3)0.2299 (5)0.3461 (3)0.0527 (15)
H15A0.9505 (3)0.2676 (5)0.3101 (3)0.063*
C16A0.8986 (3)0.2333 (5)0.3669 (3)0.0506 (14)
H16A0.8584 (3)0.2752 (5)0.3449 (3)0.061*
C17A1.0741 (3)0.2062 (6)0.3105 (3)0.063 (2)
H17A1.0538 (3)0.2819 (6)0.3061 (3)0.075*
H17B1.1240 (3)0.2173 (6)0.3168 (3)0.075*
C18A1.0373 (3)0.1438 (7)0.2526 (3)0.066 (2)
H18A1.0497 (3)0.0631 (7)0.2587 (3)0.080*
H18B1.0530 (3)0.1766 (7)0.2216 (3)0.080*
C19A0.9247 (3)0.1252 (6)0.1723 (3)0.058 (2)
H19A0.9381 (3)0.1791 (6)0.1462 (3)0.070*
H19B0.9367 (3)0.0482 (6)0.1656 (3)0.070*
C20A0.8461 (3)0.1305 (5)0.1580 (3)0.060 (2)
H20A0.8206 (3)0.1240 (5)0.1147 (3)0.072*
H20B0.8358 (3)0.2049 (5)0.1695 (3)0.072*
C21I0.5014 (5)0.0763 (11)0.0858 (4)0.062 (3)*0.470 (7)
C21J0.5061 (4)0.0238 (7)0.0960 (4)0.047 (3)*0.545 (7)
C22I0.4668 (6)0.1726 (10)0.0423 (5)0.058 (3)*0.470 (7)
C22J0.4522 (5)0.1141 (8)0.0576 (4)0.048 (3)*0.545 (7)
C23I0.4706 (6)0.2707 (11)0.0408 (5)0.072 (3)*0.470 (7)
C23J0.4551 (6)0.2749 (8)0.0013 (5)0.074 (3)*0.545 (7)
C24I0.5098 (6)0.2642 (10)0.0844 (5)0.082 (4)*0.470 (7)
C24J0.4787 (5)0.3148 (11)0.0480 (5)0.088 (4)*0.545 (7)
C25A0.5655 (4)0.4391 (6)0.0593 (3)0.092 (2)
C26A0.6416 (4)0.4808 (8)0.0344 (3)0.116 (3)
C27A0.7352 (4)0.5299 (7)0.0559 (3)0.077 (2)
H27A0.7462 (4)0.6001 (7)0.0408 (3)0.093*
H27B0.7636 (4)0.4668 (7)0.0482 (3)0.093*
C28A0.7510 (4)0.5431 (6)0.1228 (3)0.068 (2)
H28A0.7278 (4)0.6124 (6)0.1314 (3)0.082*
H28B0.7344 (4)0.4771 (6)0.1370 (3)0.082*
C29A0.8516 (4)0.5703 (6)0.2130 (3)0.077 (2)
H29A0.8136 (4)0.6074 (6)0.2229 (3)0.092*
H29B0.8902 (4)0.6242 (6)0.2239 (3)0.092*
C30A0.8780 (3)0.4664 (5)0.2513 (3)0.0530 (15)
H30A0.9167 (3)0.4288 (5)0.2426 (3)0.064*
H30B0.8962 (3)0.4900 (5)0.2937 (3)0.064*
C31A0.6553 (3)0.3081 (5)0.2894 (2)0.0439 (13)
C32A0.5947 (3)0.2740 (6)0.2402 (3)0.052 (2)
C33A0.5713 (3)0.3426 (7)0.1899 (3)0.065 (2)
H33A0.5299 (3)0.3239 (7)0.1573 (3)0.077*
C34A0.6081 (4)0.4375 (8)0.1874 (3)0.077 (2)
H34A0.5913 (4)0.4833 (8)0.1535 (3)0.092*
C35A0.6709 (3)0.4654 (6)0.2360 (3)0.059 (2)
H35A0.6958 (3)0.5297 (6)0.2339 (3)0.071*
C36A0.6968 (3)0.3984 (5)0.2874 (2)0.0431 (13)
C37A0.7708 (3)0.4145 (5)0.3341 (3)0.0511 (14)
H37A0.7692 (3)0.4197 (5)0.3742 (3)0.061*
H37B0.7897 (3)0.4857 (5)0.3271 (3)0.061*
C38A0.8185 (3)0.3139 (4)0.3303 (2)0.0421 (13)
C39A0.8389 (2)0.2987 (4)0.2814 (2)0.0397 (13)
C40A0.8729 (3)0.1987 (4)0.2706 (2)0.0419 (13)
C41A0.8887 (3)0.1128 (5)0.3140 (3)0.055 (2)
H41A0.9110 (3)0.0442 (5)0.3084 (3)0.066*
C42A0.8722 (3)0.1275 (5)0.3640 (3)0.057 (2)
H42A0.8846 (3)0.0702 (5)0.3926 (3)0.069*
C43A0.8371 (3)0.2271 (5)0.3726 (3)0.053 (2)
H43A0.8258 (3)0.2361 (5)0.4068 (3)0.064*
C44A0.8863 (3)0.1778 (5)0.2132 (3)0.0531 (15)
H44A0.9080 (3)0.2451 (5)0.2053 (3)0.064*
H44B0.9193 (3)0.1127 (5)0.2182 (3)0.064*
C45A0.8183 (3)0.1539 (5)0.1602 (2)0.0448 (13)
C46A0.7845 (3)0.0491 (4)0.1525 (2)0.0402 (12)
C47A0.7144 (3)0.0346 (5)0.1127 (2)0.0463 (14)
C48A0.6805 (3)0.1242 (6)0.0750 (3)0.064 (2)
H48A0.6341 (3)0.1157 (6)0.0471 (3)0.077*
C49A0.7149 (4)0.2263 (6)0.0783 (3)0.077 (2)
H49A0.6925 (4)0.2850 (6)0.0517 (3)0.093*
C50A0.7825 (4)0.2407 (5)0.1212 (3)0.063 (2)
H50A0.8047 (4)0.3105 (5)0.1240 (3)0.076*
C51A0.6729 (3)0.0684 (6)0.1174 (3)0.056 (2)
H51A0.6284 (3)0.0726 (6)0.0824 (3)0.067*
H51B0.7003 (3)0.1390 (6)0.1182 (3)0.067*
C52A0.6576 (3)0.0558 (5)0.1745 (3)0.0507 (15)
C53A0.6092 (3)0.0302 (6)0.1793 (3)0.059 (2)
C54A0.6039 (3)0.0579 (5)0.2348 (3)0.053 (2)
C55A0.6454 (3)0.0047 (6)0.2850 (3)0.061 (2)
H55A0.6424 (3)0.0127 (6)0.3223 (3)0.073*
C56A0.6908 (4)0.0919 (6)0.2802 (3)0.066 (2)
H56A0.7174 (4)0.1344 (6)0.3139 (3)0.080*
C57A0.6968 (3)0.1166 (5)0.2255 (3)0.061 (2)
H57A0.7280 (3)0.1755 (5)0.2229 (3)0.073*
C58A0.5589 (3)0.1625 (6)0.2402 (3)0.065 (2)
H58A0.5131 (3)0.1610 (6)0.2066 (3)0.077*
H58B0.5504 (3)0.1587 (6)0.2773 (3)0.077*
O1B0.3159 (2)0.5231 (3)0.2158 (2)0.0522 (10)
O2B0.4575 (2)0.7065 (5)0.2229 (2)0.0871 (15)
O3B0.5613 (2)0.6766 (5)0.3572 (2)0.0802 (15)
O4B0.0812 (2)0.4729 (4)0.4887 (2)0.0548 (10)
O5B0.0785 (2)0.3072 (3)0.3942 (2)0.0515 (10)
O6B0.1689 (2)0.2266 (3)0.32982 (15)0.0445 (9)
O7B0.0659 (2)0.4091 (3)0.13245 (15)0.0457 (9)
O8B0.0315 (3)0.3477 (4)0.0086 (2)0.0850 (15)
O9K0.0895 (5)0.1532 (8)0.0307 (4)0.102 (4)*0.623 (14)
O9L0.0244 (7)0.0799 (10)0.0365 (7)0.135 (7)*0.383 (14)
O10K0.2103 (7)0.0292 (15)0.0382 (9)0.145 (6)*0.354 (9)
O10L0.1649 (5)0.1046 (8)0.0415 (5)0.139 (4)*0.682 (9)
O11K0.3437 (8)0.0157 (12)0.1284 (7)0.098 (6)*0.354 (9)
O11L0.2975 (4)0.0924 (7)0.1378 (4)0.097 (3)*0.682 (9)
O12B0.3180 (2)0.1005 (3)0.2216 (2)0.0607 (11)
N1B0.3298 (2)0.6594 (4)0.4281 (2)0.0482 (11)
N2B0.3320 (2)0.5761 (4)0.4608 (2)0.0446 (11)
C1B0.3472 (3)0.6223 (6)0.2035 (3)0.068 (2)
H1B10.3359 (3)0.6898 (6)0.2237 (3)0.082*
H1B20.3279 (3)0.6353 (6)0.1603 (3)0.082*
C2B0.4284 (3)0.6039 (6)0.2259 (4)0.086 (3)
H2B10.4469 (3)0.5778 (6)0.2672 (4)0.103*
H2B20.4403 (3)0.5458 (6)0.2007 (4)0.103*
C3B0.5336 (4)0.7049 (8)0.2483 (3)0.089 (2)
H3B10.5505 (4)0.7501 (8)0.2233 (3)0.107*
H3B20.5510 (4)0.6261 (8)0.2472 (3)0.107*
C4B0.5646 (4)0.7513 (8)0.3123 (3)0.093 (3)
H4B10.6141 (4)0.7688 (8)0.3218 (3)0.111*
H4B20.5397 (4)0.8232 (8)0.3148 (3)0.111*
C5B0.5039 (3)0.6824 (6)0.3757 (3)0.060 (2)
C6B0.5079 (3)0.6054 (6)0.4192 (3)0.066 (2)
H6B0.5485 (3)0.5587 (6)0.4360 (3)0.079*
C7B0.4522 (3)0.5972 (6)0.4378 (3)0.063 (2)
H7B0.4548 (3)0.5431 (6)0.4664 (3)0.076*
C8B0.3924 (3)0.6680 (5)0.4149 (2)0.0456 (13)
C9B0.3903 (3)0.7486 (5)0.3739 (3)0.061 (2)
H9B0.3513 (3)0.7995 (5)0.3596 (3)0.074*
C10B0.4455 (4)0.7553 (6)0.3534 (3)0.068 (2)
H10B0.4429 (4)0.8090 (6)0.3246 (3)0.082*
C11B0.2677 (3)0.5613 (5)0.4704 (2)0.0410 (12)
C12B0.2085 (3)0.6361 (5)0.4512 (2)0.0446 (13)
H12B0.2108 (3)0.7055 (5)0.4339 (2)0.053*
C13B0.1473 (3)0.6083 (5)0.4574 (2)0.0482 (14)
H13B0.1080 (3)0.6586 (5)0.4445 (2)0.058*
C14B0.1434 (3)0.5044 (5)0.4833 (2)0.0457 (14)
C15B0.2022 (3)0.4324 (5)0.5051 (3)0.0492 (14)
H15B0.2004 (3)0.3648 (5)0.5240 (3)0.059*
C16B0.2642 (3)0.4615 (5)0.4986 (2)0.0484 (14)
H16B0.3043 (3)0.4131 (5)0.5136 (2)0.058*
C17B0.0220 (3)0.4531 (6)0.4330 (3)0.057 (2)
H17C0.0253 (3)0.5024 (6)0.4023 (3)0.069*
H17D0.0220 (3)0.4733 (6)0.4385 (3)0.069*
C18B0.0203 (3)0.3309 (5)0.4120 (3)0.0516 (15)
H18C0.0232 (3)0.2806 (5)0.4444 (3)0.062*
H18D0.0241 (3)0.3168 (5)0.3781 (3)0.062*
C19B0.0863 (3)0.1900 (5)0.3793 (3)0.0531 (15)
H19C0.0497 (3)0.1706 (5)0.3404 (3)0.064*
H19D0.0806 (3)0.1419 (5)0.4094 (3)0.064*
C20B0.1579 (3)0.1672 (6)0.3770 (2)0.055 (2)
H20C0.1940 (3)0.1900 (6)0.4156 (2)0.066*
H20D0.1641 (3)0.0849 (6)0.3711 (2)0.066*
C21B0.0012 (3)0.4697 (5)0.0984 (3)0.058 (2)
H21A0.0112 (3)0.5298 (5)0.0758 (3)0.070*
H21B0.0190 (3)0.5059 (5)0.1257 (3)0.070*
C22B0.0510 (3)0.3888 (6)0.0556 (3)0.072 (2)
H22A0.0559 (3)0.3239 (6)0.0780 (3)0.087*
H22B0.0971 (3)0.4281 (6)0.0388 (3)0.087*
C23B0.0162 (5)0.2488 (7)0.0200 (4)0.109 (3)
C24K0.0258 (8)0.2204 (11)0.0414 (6)0.108 (5)*0.623 (14)
C24L0.0042 (11)0.1897 (15)0.0444 (7)0.117 (7)*0.383 (14)
C25B0.0952 (5)0.0583 (9)0.0012 (6)0.161 (5)
C26K0.1437 (10)0.039 (2)0.0102 (10)0.139 (6)*0.354 (9)
C26L0.1600 (8)0.0130 (12)0.0004 (8)0.139 (5)*0.682 (9)
C27K0.2527 (8)0.1302 (13)0.0558 (9)0.090 (7)*0.354 (9)
C27L0.2199 (6)0.1856 (10)0.0471 (6)0.120 (7)*0.682 (9)
C28K0.3309 (7)0.0923 (19)0.0766 (7)0.123 (10)*0.354 (9)
C28L0.2914 (6)0.1324 (13)0.0788 (5)0.123 (5)*0.682 (9)
C29K0.3422 (14)0.0764 (14)0.1778 (6)0.087 (7)*0.354 (9)
C29L0.3653 (5)0.0442 (12)0.1702 (4)0.086 (4)*0.682 (9)
C30B0.3714 (4)0.0085 (6)0.2314 (3)0.089 (3)
C31B0.2846 (3)0.4494 (5)0.1667 (2)0.0431 (13)
C32B0.2168 (3)0.4768 (5)0.1241 (2)0.0436 (13)
C33B0.1889 (3)0.4035 (6)0.0741 (3)0.056 (2)
H33B0.1446 (3)0.4208 (6)0.0443 (3)0.067*
C34B0.2259 (4)0.3057 (6)0.0679 (3)0.069 (2)
H34B0.2081 (4)0.2603 (6)0.0327 (3)0.082*
C35B0.2888 (4)0.2743 (5)0.1131 (3)0.063 (2)
H35B0.3113 (4)0.2048 (5)0.1094 (3)0.076*
C36B0.3194 (3)0.3442 (5)0.1641 (3)0.0480 (14)
C37B0.3849 (3)0.3058 (6)0.2171 (3)0.062 (2)
H37C0.4195 (3)0.3665 (6)0.2286 (3)0.074*
H37D0.4064 (3)0.2382 (6)0.2049 (3)0.074*
C38B0.3675 (3)0.2771 (5)0.2713 (3)0.054 (2)
C39B0.3335 (3)0.1758 (5)0.2713 (3)0.0521 (15)
C40B0.3116 (3)0.1508 (5)0.3182 (3)0.053 (2)
C41B0.3277 (3)0.2269 (6)0.3667 (3)0.058 (2)
H41B0.3147 (3)0.2103 (6)0.3988 (3)0.069*
C42B0.3627 (3)0.3271 (6)0.3688 (3)0.066 (2)
H42B0.3738 (3)0.3772 (6)0.4022 (3)0.079*
C43B0.3814 (3)0.3531 (6)0.3207 (3)0.063 (2)
H43B0.4035 (3)0.4222 (6)0.3215 (3)0.075*
C44B0.2626 (3)0.0500 (5)0.3123 (3)0.059 (2)
H44C0.2822 (3)0.0197 (5)0.3001 (3)0.071*
H44D0.2594 (3)0.0373 (5)0.3510 (3)0.071*
C45B0.1889 (3)0.0768 (5)0.2654 (3)0.0495 (14)
C46B0.1473 (3)0.1687 (5)0.2745 (2)0.0420 (13)
C47B0.0866 (3)0.2105 (5)0.2282 (2)0.0419 (13)
C48B0.0630 (3)0.1483 (6)0.1739 (3)0.057 (2)
H48B0.0212 (3)0.1714 (6)0.1427 (3)0.068*
C49B0.1009 (4)0.0525 (6)0.1657 (3)0.066 (2)
H49B0.0834 (4)0.0102 (6)0.1294 (3)0.079*
C50B0.1640 (4)0.0185 (5)0.2099 (3)0.059 (2)
H50B0.1901 (4)0.0439 (5)0.2027 (3)0.071*
C51B0.0513 (3)0.3230 (5)0.2358 (3)0.0516 (15)
H51C0.0416 (3)0.3218 (5)0.2726 (3)0.062*
H51D0.0061 (3)0.3320 (5)0.2020 (3)0.062*
C52B0.0973 (3)0.4248 (5)0.2392 (2)0.0418 (13)
C53B0.1058 (3)0.4625 (5)0.1879 (2)0.0413 (13)
C54B0.1538 (3)0.5475 (5)0.1906 (2)0.0461 (13)
C55B0.1903 (3)0.5997 (5)0.2466 (3)0.0533 (15)
H55B0.2209 (3)0.6594 (5)0.2495 (3)0.064*
C56B0.1820 (3)0.5650 (5)0.2976 (3)0.055 (2)
H56B0.2075 (3)0.6003 (5)0.3348 (3)0.066*
C57B0.1363 (3)0.4786 (5)0.2941 (3)0.0522 (15)
H57B0.1315 (3)0.4556 (5)0.3292 (3)0.063*
C58B0.1717 (3)0.5751 (5)0.1362 (3)0.0522 (15)
H58C0.1281 (3)0.5854 (5)0.1009 (3)0.063*
H58D0.1977 (3)0.6462 (5)0.1442 (3)0.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.046 (2)0.066 (3)0.037 (2)0.009 (2)0.013 (2)0.001 (2)
O2A0.047 (2)0.088 (3)0.064 (3)0.005 (2)0.029 (2)0.021 (2)
O3A0.035 (2)0.102 (3)0.046 (2)0.001 (2)0.020 (2)0.011 (2)
O4A0.043 (2)0.085 (3)0.055 (2)0.003 (2)0.024 (2)0.001 (2)
O5A0.041 (2)0.086 (3)0.058 (3)0.004 (2)0.018 (2)0.021 (2)
O6A0.042 (2)0.043 (2)0.054 (2)0.001 (2)0.011 (2)0.006 (2)
O7A0.031 (2)0.121 (4)0.044 (2)0.012 (2)0.005 (2)0.024 (2)
O10A0.083 (3)0.067 (3)0.053 (3)0.008 (2)0.024 (2)0.011 (2)
O11A0.088 (4)0.078 (3)0.071 (3)0.023 (3)0.025 (3)0.017 (3)
O12A0.042 (2)0.032 (2)0.047 (2)0.007 (2)0.013 (2)0.006 (2)
N1A0.038 (2)0.041 (3)0.046 (3)0.002 (2)0.017 (2)0.004 (2)
N2A0.044 (3)0.043 (3)0.045 (3)0.002 (2)0.016 (2)0.004 (2)
C1A0.070 (4)0.087 (5)0.034 (3)0.020 (4)0.020 (3)0.007 (3)
C2A0.067 (4)0.089 (5)0.041 (3)0.004 (4)0.026 (3)0.001 (3)
C3A0.040 (3)0.125 (6)0.070 (4)0.011 (4)0.032 (3)0.027 (4)
C5A0.034 (3)0.065 (4)0.039 (3)0.002 (3)0.014 (2)0.015 (3)
C6A0.035 (3)0.065 (4)0.052 (3)0.012 (3)0.016 (3)0.001 (3)
C7A0.044 (3)0.052 (3)0.040 (3)0.008 (3)0.009 (3)0.000 (3)
C8A0.034 (3)0.051 (3)0.038 (3)0.000 (2)0.012 (2)0.008 (3)
C9A0.038 (3)0.054 (4)0.051 (3)0.006 (3)0.017 (3)0.001 (3)
C10A0.044 (3)0.049 (3)0.050 (3)0.000 (3)0.022 (3)0.002 (3)
C11A0.046 (3)0.033 (3)0.046 (3)0.001 (2)0.019 (3)0.005 (2)
C12A0.040 (3)0.049 (3)0.041 (3)0.003 (3)0.013 (3)0.003 (2)
C13A0.033 (3)0.047 (3)0.053 (3)0.006 (2)0.012 (3)0.002 (3)
C14A0.042 (3)0.048 (3)0.052 (3)0.008 (3)0.022 (3)0.008 (3)
C15A0.062 (4)0.056 (4)0.045 (3)0.003 (3)0.026 (3)0.002 (3)
C16A0.052 (3)0.049 (3)0.049 (3)0.012 (3)0.017 (3)0.004 (3)
C17A0.049 (4)0.082 (5)0.062 (4)0.014 (3)0.027 (3)0.006 (3)
C18A0.048 (4)0.096 (5)0.061 (4)0.005 (3)0.028 (3)0.009 (4)
C19A0.056 (4)0.060 (4)0.059 (4)0.009 (3)0.022 (3)0.006 (3)
C20A0.057 (4)0.038 (3)0.078 (4)0.007 (3)0.017 (3)0.002 (3)
C25A0.107 (6)0.095 (6)0.056 (4)0.002 (5)0.008 (4)0.018 (4)
C26A0.099 (7)0.203 (11)0.044 (4)0.032 (7)0.025 (4)0.022 (5)
C27A0.082 (5)0.081 (5)0.071 (5)0.000 (4)0.029 (4)0.026 (4)
C28A0.080 (5)0.054 (4)0.067 (4)0.006 (3)0.021 (4)0.011 (3)
C29A0.107 (6)0.051 (4)0.065 (5)0.038 (4)0.019 (4)0.006 (3)
C30A0.059 (4)0.045 (3)0.054 (4)0.016 (3)0.018 (3)0.004 (3)
C31A0.036 (3)0.063 (4)0.033 (3)0.008 (3)0.015 (2)0.001 (3)
C32A0.033 (3)0.084 (4)0.042 (3)0.005 (3)0.017 (3)0.007 (3)
C33A0.045 (4)0.097 (5)0.046 (4)0.013 (4)0.012 (3)0.002 (4)
C34A0.058 (4)0.118 (7)0.048 (4)0.038 (4)0.014 (3)0.026 (4)
C35A0.057 (4)0.063 (4)0.060 (4)0.020 (3)0.027 (3)0.014 (3)
C36A0.044 (3)0.049 (3)0.041 (3)0.010 (3)0.021 (3)0.003 (3)
C37A0.053 (3)0.056 (4)0.044 (3)0.007 (3)0.018 (3)0.001 (3)
C38A0.034 (3)0.042 (3)0.045 (3)0.011 (2)0.007 (2)0.005 (2)
C39A0.028 (3)0.041 (3)0.045 (3)0.012 (2)0.005 (2)0.010 (2)
C40A0.028 (3)0.031 (3)0.059 (4)0.005 (2)0.008 (2)0.000 (3)
C41A0.034 (3)0.041 (3)0.075 (4)0.002 (2)0.004 (3)0.007 (3)
C42A0.044 (3)0.056 (4)0.061 (4)0.001 (3)0.005 (3)0.024 (3)
C43A0.039 (3)0.063 (4)0.049 (3)0.012 (3)0.005 (3)0.013 (3)
C44A0.048 (3)0.038 (3)0.081 (4)0.004 (3)0.034 (3)0.004 (3)
C45A0.046 (3)0.043 (3)0.051 (3)0.001 (3)0.025 (3)0.001 (3)
C46A0.041 (3)0.036 (3)0.045 (3)0.003 (2)0.017 (3)0.007 (2)
C47A0.040 (3)0.057 (4)0.039 (3)0.007 (3)0.013 (3)0.007 (3)
C48A0.064 (4)0.064 (4)0.046 (4)0.024 (4)0.004 (3)0.011 (3)
C49A0.118 (6)0.047 (4)0.049 (4)0.031 (4)0.014 (4)0.008 (3)
C50A0.088 (5)0.041 (3)0.055 (4)0.000 (3)0.022 (4)0.002 (3)
C51A0.032 (3)0.077 (4)0.053 (4)0.011 (3)0.010 (3)0.020 (3)
C52A0.035 (3)0.059 (4)0.059 (4)0.019 (3)0.019 (3)0.015 (3)
C53A0.030 (3)0.086 (5)0.050 (4)0.019 (3)0.005 (3)0.019 (3)
C54A0.034 (3)0.072 (4)0.054 (4)0.022 (3)0.018 (3)0.020 (3)
C55A0.064 (4)0.072 (4)0.058 (4)0.029 (4)0.034 (4)0.003 (3)
C56A0.085 (5)0.057 (4)0.071 (5)0.013 (4)0.044 (4)0.013 (3)
C57A0.065 (4)0.051 (4)0.068 (4)0.020 (3)0.026 (4)0.003 (3)
C58A0.032 (3)0.113 (6)0.048 (4)0.015 (3)0.017 (3)0.026 (4)
O1B0.045 (2)0.056 (2)0.050 (2)0.015 (2)0.012 (2)0.002 (2)
O2B0.062 (3)0.095 (4)0.099 (4)0.021 (3)0.023 (3)0.002 (3)
O3B0.048 (3)0.116 (4)0.079 (3)0.027 (3)0.022 (2)0.030 (3)
O4B0.040 (2)0.080 (3)0.048 (2)0.002 (2)0.022 (2)0.006 (2)
O5B0.043 (2)0.069 (3)0.052 (2)0.008 (2)0.027 (2)0.005 (2)
O6B0.041 (2)0.055 (2)0.036 (2)0.005 (2)0.013 (2)0.004 (2)
O7B0.037 (2)0.054 (2)0.037 (2)0.004 (2)0.004 (2)0.004 (2)
O8B0.104 (4)0.073 (3)0.062 (3)0.001 (3)0.013 (3)0.005 (3)
O12B0.065 (3)0.046 (2)0.085 (3)0.017 (2)0.045 (2)0.012 (2)
N1B0.045 (3)0.050 (3)0.044 (3)0.006 (2)0.010 (2)0.004 (2)
N2B0.039 (3)0.047 (3)0.042 (3)0.008 (2)0.009 (2)0.005 (2)
C1B0.056 (4)0.059 (4)0.083 (5)0.022 (3)0.018 (3)0.000 (3)
C2B0.089 (5)0.052 (4)0.159 (8)0.027 (4)0.092 (6)0.006 (4)
C3B0.057 (4)0.130 (7)0.076 (5)0.030 (4)0.018 (4)0.006 (5)
C4B0.073 (5)0.132 (7)0.077 (5)0.045 (5)0.030 (4)0.000 (5)
C5B0.046 (4)0.069 (4)0.063 (4)0.023 (3)0.018 (3)0.003 (3)
C6B0.039 (3)0.077 (5)0.073 (4)0.009 (3)0.010 (3)0.020 (4)
C7B0.042 (3)0.079 (5)0.062 (4)0.007 (3)0.010 (3)0.029 (3)
C8B0.038 (3)0.046 (3)0.046 (3)0.009 (3)0.008 (3)0.004 (3)
C9B0.062 (4)0.053 (4)0.070 (4)0.003 (3)0.024 (3)0.015 (3)
C10B0.071 (5)0.060 (4)0.080 (5)0.010 (4)0.034 (4)0.021 (4)
C11B0.038 (3)0.047 (3)0.033 (3)0.007 (2)0.007 (2)0.003 (2)
C12B0.045 (3)0.043 (3)0.041 (3)0.002 (3)0.012 (3)0.003 (2)
C13B0.050 (3)0.050 (3)0.049 (3)0.010 (3)0.024 (3)0.001 (3)
C14B0.042 (3)0.063 (4)0.034 (3)0.001 (3)0.017 (2)0.008 (3)
C15B0.046 (3)0.049 (3)0.052 (3)0.002 (3)0.018 (3)0.005 (3)
C16B0.035 (3)0.055 (4)0.050 (3)0.000 (3)0.009 (3)0.009 (3)
C17B0.037 (3)0.080 (5)0.055 (4)0.004 (3)0.018 (3)0.000 (3)
C18B0.032 (3)0.079 (4)0.047 (3)0.002 (3)0.019 (3)0.003 (3)
C19B0.051 (3)0.061 (4)0.048 (3)0.003 (3)0.019 (3)0.003 (3)
C20B0.048 (3)0.077 (4)0.039 (3)0.010 (3)0.018 (3)0.012 (3)
C21B0.047 (3)0.072 (4)0.044 (3)0.011 (3)0.005 (3)0.014 (3)
C22B0.048 (4)0.093 (5)0.060 (4)0.001 (4)0.002 (3)0.020 (4)
C23B0.153 (9)0.092 (6)0.072 (5)0.015 (6)0.032 (6)0.021 (5)
C25B0.126 (10)0.148 (11)0.189 (13)0.006 (8)0.029 (9)0.066 (10)
C30B0.103 (6)0.076 (5)0.111 (6)0.055 (4)0.068 (5)0.034 (4)
C31B0.041 (3)0.050 (3)0.040 (3)0.010 (3)0.017 (3)0.009 (3)
C32B0.041 (3)0.048 (3)0.044 (3)0.006 (3)0.017 (3)0.008 (3)
C33B0.052 (4)0.067 (4)0.047 (4)0.014 (3)0.014 (3)0.002 (3)
C34B0.077 (5)0.065 (4)0.065 (4)0.017 (4)0.028 (4)0.009 (3)
C35B0.071 (4)0.048 (4)0.081 (5)0.000 (3)0.041 (4)0.005 (3)
C36B0.047 (3)0.049 (3)0.058 (4)0.001 (3)0.030 (3)0.008 (3)
C37B0.041 (3)0.069 (4)0.080 (4)0.006 (3)0.027 (3)0.024 (3)
C38B0.031 (3)0.061 (4)0.068 (4)0.012 (3)0.016 (3)0.023 (3)
C39B0.036 (3)0.061 (4)0.060 (4)0.017 (3)0.019 (3)0.015 (3)
C40B0.036 (3)0.063 (4)0.065 (4)0.015 (3)0.023 (3)0.020 (3)
C41B0.035 (3)0.082 (5)0.056 (4)0.011 (3)0.016 (3)0.019 (4)
C42B0.045 (4)0.081 (5)0.060 (4)0.004 (3)0.008 (3)0.014 (4)
C43B0.038 (3)0.067 (4)0.067 (4)0.001 (3)0.001 (3)0.016 (4)
C44B0.056 (4)0.056 (4)0.078 (4)0.016 (3)0.037 (3)0.023 (3)
C45B0.057 (4)0.050 (3)0.053 (4)0.004 (3)0.034 (3)0.009 (3)
C46B0.037 (3)0.053 (3)0.039 (3)0.005 (3)0.018 (3)0.003 (3)
C47B0.037 (3)0.051 (3)0.042 (3)0.012 (3)0.019 (3)0.003 (3)
C48B0.056 (4)0.068 (4)0.046 (4)0.018 (3)0.017 (3)0.007 (3)
C49B0.090 (5)0.058 (4)0.053 (4)0.027 (4)0.030 (4)0.005 (3)
C50B0.080 (5)0.044 (3)0.070 (4)0.010 (3)0.047 (4)0.002 (3)
C51B0.032 (3)0.077 (4)0.045 (3)0.006 (3)0.013 (3)0.018 (3)
C52B0.033 (3)0.055 (3)0.037 (3)0.013 (2)0.013 (2)0.008 (3)
C53B0.032 (3)0.048 (3)0.039 (3)0.007 (2)0.009 (2)0.000 (2)
C54B0.045 (3)0.042 (3)0.046 (3)0.010 (3)0.012 (3)0.010 (3)
C55B0.051 (3)0.048 (3)0.054 (4)0.000 (3)0.013 (3)0.003 (3)
C56B0.052 (4)0.057 (4)0.049 (4)0.012 (3)0.011 (3)0.008 (3)
C57B0.054 (4)0.057 (4)0.046 (3)0.013 (3)0.021 (3)0.000 (3)
C58B0.048 (3)0.049 (3)0.054 (4)0.001 (3)0.011 (3)0.012 (3)
Geometric parameters (Å, º) top
O1A—C31A1.389 (6)O1B—C1B1.429 (7)
O1A—C1A1.435 (7)O2B—C2B1.366 (7)
O2A—C2A1.403 (8)O2B—C3B1.427 (8)
O2A—C3A1.426 (7)O3B—C5B1.391 (7)
O3A—C5A1.365 (6)O3B—C4B1.428 (8)
O3A—C4I1.394 (10)O4B—C14B1.381 (6)
O3A—C4J1.448 (6)O4B—C17B1.432 (7)
O4A—C14A1.372 (6)O5B—C19B1.412 (7)
O4A—C17A1.414 (7)O5B—C18B1.413 (6)
O5A—C19A1.406 (7)O6B—C46B1.379 (6)
O5A—C18A1.433 (7)O6B—C20B1.436 (6)
O6A—C46A1.383 (6)O7B—C53B1.397 (6)
O6A—C20A1.442 (7)O7B—C21B1.429 (6)
O7A—C53A1.377 (8)O8B—C22B1.389 (8)
O7A—C21I1.408 (9)O8B—C23B1.439 (9)
O7A—C21J1.499 (8)O9K—C25B1.340 (8)
O8I—C22I1.436 (9)O9K—C24K1.426 (8)
O8I—C23I1.445 (9)O9L—C24L1.369 (9)
O8J—C23J1.419 (8)O9L—C25B1.394 (9)
O8J—C22J1.422 (8)O10K—C27K1.406 (10)
O9I—C25A1.406 (8)O10K—C26K1.410 (10)
O9I—C24I1.424 (9)O10L—C27L1.401 (9)
O9J—C24J1.406 (9)O10L—C26L1.450 (10)
O9J—C25A1.463 (7)O11K—C29K1.409 (10)
O10A—C26A1.390 (8)O11K—C28K1.441 (10)
O10A—C27A1.408 (8)O11L—C29L1.422 (8)
O11A—C29A1.382 (8)O11L—C28L1.428 (9)
O11A—C28A1.425 (8)O12B—C39B1.391 (7)
O12A—C39A1.406 (6)O12B—C30B1.451 (7)
O12A—C30A1.420 (6)N1B—N2B1.255 (6)
N1A—N2A1.255 (6)N1B—C8B1.427 (7)
N1A—C8A1.430 (6)N2B—C11B1.426 (7)
N2A—C11A1.423 (7)C1B—C2B1.535 (7)
C1A—C2A1.490 (8)C3B—C4B1.503 (10)
C3A—C4J1.493 (8)C5B—C10B1.373 (9)
C3A—C4I1.511 (11)C5B—C6B1.375 (8)
C5A—C6A1.375 (8)C6B—C7B1.372 (8)
C5A—C10A1.383 (7)C7B—C8B1.378 (8)
C6A—C7A1.376 (8)C8B—C9B1.369 (8)
C7A—C8A1.391 (7)C9B—C10B1.388 (9)
C8A—C9A1.381 (8)C11B—C16B1.380 (7)
C9A—C10A1.392 (7)C11B—C12B1.393 (7)
C11A—C16A1.364 (7)C12B—C13B1.356 (7)
C11A—C12A1.389 (7)C13B—C14B1.394 (8)
C12A—C13A1.367 (7)C14B—C15B1.371 (8)
C13A—C14A1.382 (8)C15B—C16B1.379 (7)
C14A—C15A1.382 (8)C17B—C18B1.483 (8)
C15A—C16A1.390 (8)C19B—C20B1.487 (8)
C17A—C18A1.500 (8)C21B—C22B1.492 (9)
C19A—C20A1.502 (8)C23B—C24L1.57 (2)
C21I—C22I1.515 (9)C23B—C24K1.572 (13)
C21J—C22J1.536 (8)C25B—C26L1.533 (10)
C23I—C24I1.531 (9)C25B—C26K1.549 (10)
C23J—C24J1.524 (9)C27K—C28K1.549 (10)
C25A—C26A1.518 (7)C27L—C28L1.502 (9)
C27A—C28A1.509 (7)C29K—C30B1.526 (10)
C29A—C30A1.497 (8)C29L—C30B1.526 (9)
C31A—C36A1.382 (8)C31B—C36B1.399 (8)
C31A—C32A1.397 (8)C31B—C32B1.399 (7)
C32A—C33A1.383 (9)C32B—C33B1.385 (8)
C32A—C58A1.509 (9)C32B—C58B1.522 (8)
C33A—C34A1.370 (10)C33B—C34B1.371 (9)
C34A—C35A1.398 (9)C34B—C35B1.369 (9)
C35A—C36A1.394 (8)C35B—C36B1.384 (9)
C36A—C37A1.506 (8)C36B—C37B1.513 (8)
C37A—C38A1.511 (8)C37B—C38B1.519 (8)
C38A—C39A1.384 (7)C38B—C39B1.386 (8)
C38A—C43A1.392 (7)C38B—C43B1.391 (9)
C39A—C40A1.393 (7)C39B—C40B1.397 (8)
C40A—C41A1.405 (8)C40B—C41B1.373 (9)
C40A—C44A1.506 (8)C40B—C44B1.531 (9)
C41A—C42A1.362 (9)C41B—C42B1.376 (9)
C42A—C43A1.385 (9)C42B—C43B1.385 (9)
C44A—C45A1.503 (8)C44B—C45B1.519 (8)
C45A—C50A1.383 (8)C45B—C50B1.385 (8)
C45A—C46A1.391 (7)C45B—C46B1.396 (8)
C46A—C47A1.390 (7)C46B—C47B1.393 (7)
C47A—C48A1.384 (8)C47B—C48B1.384 (8)
C47A—C51A1.520 (8)C47B—C51B1.504 (8)
C48A—C49A1.383 (10)C48B—C49B1.378 (9)
C49A—C50A1.376 (10)C49B—C50B1.370 (9)
C51A—C52A1.511 (8)C51B—C52B1.514 (8)
C52A—C57A1.380 (8)C52B—C57B1.387 (8)
C52A—C53A1.405 (8)C52B—C53B1.390 (7)
C53A—C54A1.396 (8)C53B—C54B1.395 (8)
C54A—C55A1.387 (9)C54B—C55B1.387 (8)
C54A—C58A1.521 (9)C54B—C58B1.524 (8)
C55A—C56A1.374 (9)C55B—C56B1.371 (8)
C56A—C57A1.375 (9)C56B—C57B1.369 (8)
O1B—C31B1.381 (6)
C31A—O1A—C1A113.6 (4)C31B—O1B—C1B115.1 (4)
C2A—O2A—C3A112.2 (5)C2B—O2B—C3B114.1 (6)
C5A—O3A—C4I120.0 (11)C5B—O3B—C4B121.2 (6)
C5A—O3A—C4J114.5 (4)C14B—O4B—C17B115.6 (4)
C14A—O4A—C17A121.0 (5)C19B—O5B—C18B113.9 (4)
C19A—O5A—C18A113.1 (4)C46B—O6B—C20B115.1 (4)
C46A—O6A—C20A114.2 (4)C53B—O7B—C21B114.2 (4)
C53A—O7A—C21I129.6 (6)C22B—O8B—C23B117.2 (5)
C53A—O7A—C21J104.5 (5)C25B—O9K—C24K114.6 (8)
C22I—O8I—C23I109.6 (7)C24L—O9L—C25B121.3 (11)
C23J—O8J—C22J112.1 (6)C27K—O10K—C26K117.7 (11)
C25A—O9I—C24I109.2 (7)C27L—O10L—C26L113.6 (8)
C24J—O9J—C25A114.9 (7)C29K—O11K—C28K110.5 (9)
C26A—O10A—C27A113.2 (5)C29L—O11L—C28L111.1 (7)
C29A—O11A—C28A114.4 (6)C39B—O12B—C30B112.4 (5)
C39A—O12A—C30A113.7 (4)N2B—N1B—C8B113.7 (4)
N2A—N1A—C8A114.5 (4)N1B—N2B—C11B114.2 (4)
N1A—N2A—C11A113.4 (4)O1B—C1B—C2B109.7 (5)
O1A—C1A—C2A113.9 (5)O2B—C2B—C1B108.1 (6)
O2A—C2A—C1A110.3 (5)O2B—C3B—C4B113.8 (7)
O2A—C3A—C4J108.0 (5)O3B—C4B—C3B115.4 (7)
O2A—C3A—C4I102.5 (10)C10B—C5B—C6B119.6 (6)
O3A—C4I—C3A115.7 (10)C10B—C5B—O3B125.6 (6)
O3A—C4J—C3A113.5 (5)C6B—C5B—O3B114.8 (6)
O3A—C5A—C6A120.7 (5)C7B—C6B—C5B120.2 (6)
O3A—C5A—C10A118.9 (5)C6B—C7B—C8B120.9 (6)
C6A—C5A—C10A120.3 (5)C9B—C8B—C7B118.6 (5)
C5A—C6A—C7A120.9 (5)C9B—C8B—N1B116.6 (5)
C6A—C7A—C8A119.5 (5)C7B—C8B—N1B124.7 (5)
C9A—C8A—C7A119.5 (5)C8B—C9B—C10B120.9 (6)
C9A—C8A—N1A115.9 (5)C5B—C10B—C9B119.7 (6)
C7A—C8A—N1A124.6 (5)C16B—C11B—C12B118.8 (5)
C8A—C9A—C10A120.9 (5)C16B—C11B—N2B115.9 (5)
C5A—C10A—C9A118.7 (5)C12B—C11B—N2B125.2 (5)
C16A—C11A—C12A119.1 (5)C13B—C12B—C11B120.4 (5)
C16A—C11A—N2A116.9 (5)C12B—C13B—C14B120.1 (5)
C12A—C11A—N2A123.9 (5)C15B—C14B—O4B118.6 (5)
C13A—C12A—C11A120.4 (5)C15B—C14B—C13B120.2 (5)
C12A—C13A—C14A119.8 (5)O4B—C14B—C13B121.2 (5)
O4A—C14A—C13A114.8 (5)C14B—C15B—C16B119.2 (5)
O4A—C14A—C15A124.8 (5)C15B—C16B—C11B121.1 (5)
C13A—C14A—C15A120.4 (5)O4B—C17B—C18B111.5 (5)
C14A—C15A—C16A118.5 (5)O5B—C18B—C17B109.2 (5)
C11A—C16A—C15A121.3 (5)O5B—C19B—C20B110.3 (5)
O4A—C17A—C18A115.4 (5)O6B—C20B—C19B113.7 (5)
O5A—C18A—C17A110.0 (5)O7B—C21B—C22B110.4 (5)
O5A—C19A—C20A108.6 (5)O8B—C22B—C21B113.4 (6)
O6A—C20A—C19A112.6 (5)O8B—C23B—C24L102.9 (7)
O7A—C21I—C22I117.4 (9)O8B—C23B—C24K105.4 (7)
O7A—C21J—C22J102.4 (6)O9K—C24K—C23B110.1 (8)
O8I—C22I—C21I108.7 (8)O9L—C24L—C23B107.4 (11)
O8J—C22J—C21J108.2 (6)O9L—C25B—C26L138.9 (14)
O8I—C23I—C24I104.8 (8)O9K—C25B—C26K114.1 (16)
O8J—C23J—C24J110.0 (8)O10K—C26K—C25B106.0 (10)
O9I—C24I—C23I107.7 (8)O10L—C26L—C25B102.3 (8)
O9J—C24J—C23J111.9 (8)O10K—C27K—C28K106.0 (9)
O9I—C25A—C26A101.7 (6)O10L—C27L—C28L110.7 (8)
O9J—C25A—C26A115.9 (6)O11K—C28K—C27K106.8 (8)
O10A—C26A—C25A109.5 (6)O11L—C28L—C27L109.2 (8)
O10A—C27A—C28A107.0 (6)O11K—C29K—C30B104.1 (12)
O11A—C28A—C27A105.4 (6)O11L—C29L—C30B112.4 (8)
O11A—C29A—C30A116.1 (6)O12B—C30B—C29L108.8 (7)
O12A—C30A—C29A110.4 (5)O12B—C30B—C29K106.5 (11)
C36A—C31A—O1A120.0 (5)O1B—C31B—C36B118.3 (5)
C36A—C31A—C32A123.1 (5)O1B—C31B—C32B119.7 (5)
O1A—C31A—C32A116.7 (5)C36B—C31B—C32B121.8 (5)
C33A—C32A—C31A117.6 (6)C33B—C32B—C31B117.7 (5)
C33A—C32A—C58A121.0 (6)C33B—C32B—C58B121.0 (5)
C31A—C32A—C58A121.3 (5)C31B—C32B—C58B120.9 (5)
C34A—C33A—C32A121.2 (6)C34B—C33B—C32B120.8 (6)
C33A—C34A—C35A119.8 (6)C33B—C34B—C35B120.5 (6)
C36A—C35A—C34A121.0 (6)C34B—C35B—C36B121.2 (6)
C31A—C36A—C35A116.9 (5)C35B—C36B—C31B117.3 (5)
C31A—C36A—C37A121.8 (5)C35B—C36B—C37B121.8 (6)
C35A—C36A—C37A120.8 (5)C31B—C36B—C37B120.8 (5)
C36A—C37A—C38A109.7 (4)C36B—C37B—C38B112.0 (4)
C39A—C38A—C43A117.7 (5)C39B—C38B—C43B118.0 (6)
C39A—C38A—C37A121.1 (5)C39B—C38B—C37B120.2 (6)
C43A—C38A—C37A120.8 (5)C43B—C38B—C37B121.8 (6)
C38A—C39A—C40A123.3 (5)C38B—C39B—O12B118.4 (5)
C38A—C39A—O12A117.8 (5)C38B—C39B—C40B121.8 (6)
C40A—C39A—O12A118.8 (5)O12B—C39B—C40B119.8 (6)
C39A—C40A—C41A116.4 (5)C41B—C40B—C39B118.3 (6)
C39A—C40A—C44A122.4 (5)C41B—C40B—C44B120.3 (5)
C41A—C40A—C44A121.0 (5)C39B—C40B—C44B120.9 (6)
C42A—C41A—C40A121.5 (6)C40B—C41B—C42B121.3 (6)
C41A—C42A—C43A120.5 (5)C41B—C42B—C43B119.7 (7)
C42A—C43A—C38A120.4 (6)C42B—C43B—C38B120.8 (6)
C45A—C44A—C40A111.4 (4)C45B—C44B—C40B109.7 (5)
C50A—C45A—C46A117.2 (5)C50B—C45B—C46B118.0 (6)
C50A—C45A—C44A120.6 (5)C50B—C45B—C44B120.9 (6)
C46A—C45A—C44A121.8 (5)C46B—C45B—C44B120.8 (5)
O6A—C46A—C47A119.5 (5)O6B—C46B—C47B117.7 (5)
O6A—C46A—C45A118.1 (5)O6B—C46B—C45B119.9 (5)
C47A—C46A—C45A122.3 (5)C47B—C46B—C45B122.2 (5)
C48A—C47A—C46A118.0 (6)C48B—C47B—C46B117.4 (5)
C48A—C47A—C51A120.7 (5)C48B—C47B—C51B121.6 (5)
C46A—C47A—C51A120.6 (5)C46B—C47B—C51B120.9 (5)
C49A—C48A—C47A120.7 (6)C49B—C48B—C47B120.6 (6)
C50A—C49A—C48A119.6 (6)C50B—C49B—C48B121.3 (6)
C49A—C50A—C45A121.7 (6)C49B—C50B—C45B120.1 (6)
C52A—C51A—C47A109.3 (4)C47B—C51B—C52B111.9 (4)
C57A—C52A—C53A118.0 (6)C57B—C52B—C53B117.5 (5)
C57A—C52A—C51A121.5 (6)C57B—C52B—C51B121.2 (5)
C53A—C52A—C51A119.9 (6)C53B—C52B—C51B121.1 (5)
O7A—C53A—C54A118.4 (6)C52B—C53B—C54B122.3 (5)
O7A—C53A—C52A120.4 (5)C52B—C53B—O7B117.6 (5)
C54A—C53A—C52A121.0 (6)C54B—C53B—O7B120.0 (5)
C55A—C54A—C53A118.5 (6)C55B—C54B—C53B117.4 (5)
C55A—C54A—C58A121.8 (5)C55B—C54B—C58B120.2 (5)
C53A—C54A—C58A119.4 (6)C53B—C54B—C58B122.1 (5)
C56A—C55A—C54A120.9 (6)C56B—C55B—C54B121.1 (6)
C55A—C56A—C57A120.1 (7)C57B—C56B—C55B120.4 (6)
C56A—C57A—C52A121.4 (6)C56B—C57B—C52B121.1 (6)
C32A—C58A—C54A111.9 (4)C32B—C58B—C54B109.6 (4)

Experimental details

(1)(2a)(2b)
Crystal data
Chemical formulaC58H64N2O12C58H64N2O12C58H64N2O12
Mr981.11981.11981.11
Crystal system, space groupMonoclinic, P21/aMonoclinic, P21/aTriclinic, P1
Temperature (K)243273213
a, b, c (Å)13.667 (4), 18.647 (11), 20.188 (6)20.341 (6), 11.709 (3), 23.875 (8)20.285 (8), 11.608 (4), 23.894 (6)
α, β, γ (°)90, 90.72 (2), 9090, 112.39 (2), 9092.22 (3), 112.32 (2), 87.81 (3)
V3)5145 (4)5258 (3)5199 (3)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.090.09
Crystal size (mm)0.70 × 0.60 × 0.500.65 × 0.60 × 0.500.65 × 0.60 × 0.50
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6514, 6301, 2449 7559, 7304, 3495 13177, 12513, 8852
Rint0.020.0170.021
θmax (°)222323
(sin θ/λ)max1)0.5270.5500.550
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.127, 0.385, 1.11 0.107, 0.367, 1.07 0.080, 0.245, 0.97
No. of reflections4701569612460
No. of parameters6286361290
No. of restraints7975104
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1798P)2 + 16.015P],
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.1516P)2 + 13.1365P],
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.1351P)2 + 11.9644P],
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.49, 0.600.56, 0.330.66, 0.50

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), MolEN (Fair, 1990), SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), SHELXTL (Sheldrick, 1993).

 
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