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
| Crystallographic Information File (CIF) Contains datablocks 1, 2a, 2b |
| Structure factor file (CIF format) Contains datablock 1 |
| Structure factor file (CIF format) Contains datablock 2a |
| Structure factor file (CIF format) Contains datablock 2b |
CCDC references: 131741; 131742; 131743
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).
Crystal data top
C58H64N2O12 | F(000) = 2088 |
Mr = 981.11 | Dx = 1.267 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 13.667 (4) Å | Cell parameters from 25 reflections |
b = 18.647 (11) Å | θ = 8–12° |
c = 20.188 (6) Å | µ = 0.09 mm−1 |
β = 90.72 (2)° | T = 243 K |
V = 5145 (4) Å3 | Parallelepiped, orange |
Z = 4 | 0.70 × 0.60 × 0.50 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.02 |
Radiation source: fine-focus sealed tube | θmax = 22°, θmin = 1° |
Graphite monochromator | h = 0→14 |
ω/2θ scans | k = 0→19 |
6514 measured reflections | l = −21→21 |
6301 independent reflections | 3 standard reflections every 60 min |
2449 reflections with I > 2σ(I) | intensity decay: 4.7% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.127 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.385 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1798P)2 + 16.015P], where P = (Fo2 + 2Fc2)/3 |
4701 reflections | (Δ/σ)max = 0.019 |
628 parameters | Δρmax = 1.49 e Å−3 |
79 restraints | Δρmin = −0.60 e Å−3 |
Crystal data top
C58H64N2O12 | V = 5145 (4) Å3 |
Mr = 981.11 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 13.667 (4) Å | µ = 0.09 mm−1 |
b = 18.647 (11) Å | T = 243 K |
c = 20.188 (6) Å | 0.70 × 0.60 × 0.50 mm |
β = 90.72 (2)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.02 |
6514 measured reflections | θmax = 22° |
6301 independent reflections | 3 standard reflections every 60 min |
2449 reflections with I > 2σ(I) | intensity decay: 4.7% |
Refinement top
R[F2 > 2σ(F2)] = 0.127 | 79 restraints |
wR(F2) = 0.385 | H-atom parameters constrained |
S = 1.11 | Δρmax = 1.49 e Å−3 |
4701 reflections | Δρmin = −0.60 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.0606 (7) | −0.0561 (7) | 0.7024 (5) | 0.095 (3) | |
O2 | 0.0060 (8) | −0.1197 (7) | 0.5719 (6) | 0.119 (4) | |
O3 | 0.1031 (9) | −0.1084 (7) | 0.4428 (5) | 0.105 (4) | |
O4 | 0.7809 (7) | −0.1316 (7) | 0.7837 (6) | 0.105 (4) | |
O5 | 0.6100 (7) | −0.1667 (5) | 0.8658 (4) | 0.074 (3) | |
O6 | 0.4234 (6) | −0.0695 (5) | 0.8870 (4) | 0.071 (3) | |
O7 | 0.3796 (6) | 0.0714 (5) | 0.6844 (4) | 0.067 (2) | |
O8 | 0.3940 (9) | 0.2168 (6) | 0.6361 (5) | 0.117 (4) | |
O9A | 0.3056 (12) | 0.3212 (7) | 0.7756 (7) | 0.063 (8)* | 0.49 (3) |
O9B | 0.2386 (14) | 0.3188 (9) | 0.7435 (11) | 0.138 (12)* | 0.51 (3) |
O10A | 0.1754 (15) | 0.3690 (11) | 0.8819 (9) | 0.144 (10)* | 0.58 (2) |
O10B | 0.2716 (16) | 0.3211 (12) | 0.8776 (9) | 0.108 (11)* | 0.41 (2) |
O11 | 0.1182 (8) | 0.2084 (5) | 0.9732 (5) | 0.101 (3) | |
O12 | 0.1126 (6) | 0.0695 (5) | 0.9141 (4) | 0.059 (2) | |
N1 | 0.4860 | −0.1114 | 0.5552 | 0.150* | |
N2 | 0.5314 | −0.1457 | 0.5857 | 0.150* | |
C1A | −0.0310 (13) | −0.0878 (15) | 0.6834 (11) | 0.083 (11)* | 0.58 (4) |
C1B | −0.0278 (18) | −0.0479 (18) | 0.6634 (17) | 0.083 (14)* | 0.42 (4) |
C2A | −0.047 (2) | −0.0690 (14) | 0.6104 (10) | 0.094 (12)* | 0.58 (4) |
C2B | −0.057 (2) | −0.1171 (18) | 0.6275 (13) | 0.088 (16)* | 0.42 (4) |
C3 | −0.0417 (11) | −0.1133 (9) | 0.5091 (7) | 0.104 (5) | |
H3A | −0.0483 (11) | −0.0633 (9) | 0.4966 (7) | 0.125* | |
H3B | −0.1063 (11) | −0.1348 (9) | 0.5101 (7) | 0.125* | |
C4 | 0.0235 (11) | −0.1530 (9) | 0.4606 (8) | 0.096 (5) | |
H4A | 0.0479 (11) | −0.1967 (9) | 0.4810 (8) | 0.115* | |
H4B | −0.0141 (11) | −0.1660 (9) | 0.4214 (8) | 0.115* | |
C5 | 0.1951 (10) | −0.1249 (9) | 0.4707 (7) | 0.092 (4) | |
C6 | 0.2343 (11) | −0.1870 (9) | 0.5011 (9) | 0.127 (6) | |
H6 | 0.1980 (11) | −0.2289 (9) | 0.5056 (9) | 0.152* | |
C7 | 0.3328 (9) | −0.1817 (9) | 0.5244 (9) | 0.136 (7) | |
H7 | 0.3576 (9) | −0.2227 (9) | 0.5448 (9) | 0.163* | |
C8 | 0.3957 (12) | −0.1256 (9) | 0.5211 (11) | 0.166 (9) | |
C9 | 0.3503 (10) | −0.0692 (11) | 0.4905 (8) | 0.133 (7) | |
H9 | 0.3872 (10) | −0.0275 (11) | 0.4871 (8) | 0.160* | |
C10 | 0.2565 (10) | −0.0658 (10) | 0.4639 (8) | 0.105 (5) | |
H10 | 0.2350 (10) | −0.0249 (10) | 0.4418 (8) | 0.126* | |
C11 | 0.6007 (8) | −0.1503 (7) | 0.6343 (6) | 0.157 (12) | |
C12 | 0.6191 (13) | −0.2123 (7) | 0.6697 (8) | 0.149 (10) | |
H12 | 0.5910 (13) | −0.2555 (7) | 0.6566 (8) | 0.179* | |
C13 | 0.6780 (11) | −0.2095 (8) | 0.7229 (7) | 0.101 (5) | |
H13 | 0.6897 (11) | −0.2479 (8) | 0.7513 (7) | 0.121* | |
C14 | 0.7186 (10) | −0.1432 (8) | 0.7305 (7) | 0.085 (5) | |
C15 | 0.7102 (9) | −0.0806 (8) | 0.6967 (6) | 0.094 (5) | |
H15 | 0.7439 (9) | −0.0389 (8) | 0.7080 (6) | 0.112* | |
C16 | 0.6488 (9) | −0.0858 (6) | 0.6461 (7) | 0.128 (7) | |
H16 | 0.6378 (9) | −0.0466 (6) | 0.6185 (7) | 0.154* | |
C17 | 0.7755 (12) | −0.1816 (9) | 0.8366 (8) | 0.103 (5) | |
H17A | 0.8396 (12) | −0.1882 (9) | 0.8568 (8) | 0.124* | |
H17B | 0.7528 (12) | −0.2276 (9) | 0.8201 (8) | 0.124* | |
C18 | 0.7054 (11) | −0.1528 (9) | 0.8866 (8) | 0.093 (5) | |
H18A | 0.7177 (11) | −0.1752 (9) | 0.9292 (8) | 0.111* | |
H18B | 0.7148 (11) | −0.1015 (9) | 0.8915 (8) | 0.111* | |
C19 | 0.5399 (11) | −0.1611 (8) | 0.9172 (8) | 0.089 (5) | |
H19A | 0.5691 (11) | −0.1796 (8) | 0.9578 (8) | 0.106* | |
H19B | 0.4846 (11) | −0.1916 (8) | 0.9060 (8) | 0.106* | |
C20 | 0.5020 (12) | −0.0861 (8) | 0.9307 (8) | 0.084 (5) | |
H20A | 0.4800 (12) | −0.0830 (8) | 0.9761 (8) | 0.101* | |
H20B | 0.5543 (12) | −0.0517 (8) | 0.9249 (8) | 0.101* | |
C21 | 0.4332 (11) | 0.0904 (8) | 0.6280 (7) | 0.087 (5) | |
H21A | 0.3919 (11) | 0.0862 (8) | 0.5888 (7) | 0.104* | |
H21B | 0.4883 (11) | 0.0581 (8) | 0.6232 (7) | 0.104* | |
C22 | 0.4690 (12) | 0.1647 (9) | 0.6345 (9) | 0.116 (7) | |
H22A | 0.5079 (12) | 0.1685 (9) | 0.6748 (9) | 0.139* | |
H22B | 0.5114 (12) | 0.1751 (9) | 0.5976 (9) | 0.139* | |
C23 | 0.3589 (13) | 0.2354 (7) | 0.6993 (6) | 0.124 (7) | |
C24A | 0.328 (3) | 0.3114 (9) | 0.7062 (9) | 0.077 (11)* | 0.49 (3) |
C24B | 0.279 (3) | 0.294 (2) | 0.6838 (10) | 0.110 (15)* | 0.51 (3) |
C25 | 0.2545 (11) | 0.3868 (6) | 0.7769 (6) | 0.102 (6) | |
C26A | 0.2542 (15) | 0.4041 (12) | 0.8509 (8) | 0.092 (9)* | 0.58 (2) |
C26B | 0.218 (2) | 0.3782 (19) | 0.8470 (11) | 0.104 (13)* | 0.41 (2) |
C27A | 0.188 (2) | 0.2969 (12) | 0.9046 (15) | 0.099 (10)* | 0.58 (2) |
C27B | 0.225 (2) | 0.2945 (16) | 0.9349 (10) | 0.080 (11)* | 0.41 (2) |
C28A | 0.107 (2) | 0.2812 (10) | 0.9548 (16) | 0.137 (14)* | 0.58 (2) |
C28B | 0.142 (2) | 0.2442 (16) | 0.9128 (10) | 0.088 (12)* | 0.41 (2) |
C29 | 0.0305 (9) | 0.1678 (6) | 0.9668 (9) | 0.095 (5) | |
C30A | 0.061 (2) | 0.0881 (6) | 0.9735 (10) | 0.099 (19)* | 0.50 |
C30B | 0.0540 (19) | 0.0884 (6) | 0.9695 (12) | 0.067 (17)* | 0.50 |
C31 | 0.0795 (10) | 0.0159 (10) | 0.7127 (8) | 0.076 (4) | |
C32 | 0.0341 (9) | 0.0507 (10) | 0.7656 (8) | 0.074 (4) | |
C33 | 0.0485 (10) | 0.1223 (11) | 0.7722 (7) | 0.081 (5) | |
H33 | 0.0159 (10) | 0.1473 (11) | 0.8051 (7) | 0.097* | |
C34 | 0.1105 (13) | 0.1585 (10) | 0.7308 (9) | 0.098 (5) | |
H34 | 0.1207 (13) | 0.2074 (10) | 0.7363 (9) | 0.118* | |
C35 | 0.1585 (10) | 0.1209 (11) | 0.6800 (8) | 0.088 (5) | |
H35 | 0.1998 (10) | 0.1455 (11) | 0.6517 (8) | 0.105* | |
C36 | 0.1453 (10) | 0.0508 (10) | 0.6723 (7) | 0.071 (4) | |
C37 | 0.2066 (10) | 0.0065 (9) | 0.6243 (7) | 0.086 (5) | |
H37A | 0.2360 (10) | 0.0380 (9) | 0.5919 (7) | 0.103* | |
H37B | 0.1649 (10) | −0.0274 (9) | 0.6009 (7) | 0.103* | |
C38 | 0.2873 (10) | −0.0342 (8) | 0.6626 (6) | 0.066 (4) | |
C39 | 0.3662 (10) | −0.0017 (8) | 0.6936 (7) | 0.064 (4) | |
C40 | 0.4311 (9) | −0.0396 (7) | 0.7331 (6) | 0.055 (3) | |
C41 | 0.4168 (11) | −0.1134 (8) | 0.7395 (8) | 0.077 (4) | |
H41 | 0.4576 (11) | −0.1398 (8) | 0.7675 (8) | 0.092* | |
C42 | 0.3451 (13) | −0.1467 (8) | 0.7059 (9) | 0.085 (5) | |
H42 | 0.3411 (13) | −0.1964 (8) | 0.7073 (9) | 0.102* | |
C43 | 0.2766 (11) | −0.1084 (11) | 0.6688 (7) | 0.079 (5) | |
H43 | 0.2243 (11) | −0.1319 (11) | 0.6484 (7) | 0.095* | |
C44 | 0.5043 (8) | −0.0006 (7) | 0.7755 (7) | 0.067 (4) | |
H44A | 0.5408 (8) | 0.0328 (7) | 0.7485 (7) | 0.080* | |
H44B | 0.5501 (8) | −0.0347 (7) | 0.7949 (7) | 0.080* | |
C45 | 0.4522 (8) | 0.0403 (8) | 0.8307 (6) | 0.061 (4) | |
C46 | 0.4068 (8) | 0.0039 (7) | 0.8818 (6) | 0.053 (3) | |
C47 | 0.3446 (9) | 0.0370 (7) | 0.9243 (6) | 0.061 (3) | |
C48 | 0.3301 (10) | 0.1092 (9) | 0.9185 (7) | 0.071 (4) | |
H48 | 0.2856 (10) | 0.1321 (9) | 0.9458 (7) | 0.085* | |
C49 | 0.3811 (11) | 0.1481 (8) | 0.8726 (8) | 0.075 (4) | |
H49 | 0.3745 (11) | 0.1977 (8) | 0.8708 (8) | 0.090* | |
C50 | 0.4422 (10) | 0.1132 (7) | 0.8290 (7) | 0.072 (4) | |
H50 | 0.4769 (10) | 0.1397 (7) | 0.7981 (7) | 0.086* | |
C51 | 0.2743 (11) | −0.0068 (8) | 0.9680 (7) | 0.077 (4) | |
H51A | 0.3120 (11) | −0.0426 (8) | 0.9921 (7) | 0.092* | |
H51B | 0.2455 (11) | 0.0251 (8) | 1.0003 (7) | 0.092* | |
C52 | 0.1946 (11) | −0.0433 (8) | 0.9309 (6) | 0.063 (4) | |
C53 | 0.1197 (11) | −0.0034 (7) | 0.9019 (7) | 0.062 (4) | |
C54 | 0.0504 (10) | −0.0342 (8) | 0.8590 (8) | 0.073 (4) | |
C55 | 0.0564 (12) | −0.1072 (9) | 0.8491 (8) | 0.080 (4) | |
H55 | 0.0098 (12) | −0.1289 (9) | 0.8217 (8) | 0.097* | |
C56 | 0.1268 (14) | −0.1489 (8) | 0.8772 (10) | 0.094 (5) | |
H56 | 0.1284 (14) | −0.1979 (8) | 0.8690 (10) | 0.113* | |
C57 | 0.1956 (15) | −0.1174 (10) | 0.9179 (9) | 0.100 (6) | |
H57 | 0.2440 (15) | −0.1458 (10) | 0.9374 (9) | 0.120* | |
C58 | −0.0204 (10) | 0.0125 (9) | 0.8201 (8) | 0.084 (5) | |
H58A | −0.0500 (10) | 0.0474 (9) | 0.8493 (8) | 0.101* | |
H58B | −0.0720 (10) | −0.0169 (9) | 0.8010 (8) | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.059 (6) | 0.135 (10) | 0.091 (8) | −0.031 (6) | −0.002 (5) | −0.025 (7) |
O2 | 0.100 (8) | 0.163 (12) | 0.093 (8) | −0.009 (8) | 0.019 (7) | −0.039 (8) |
O3 | 0.102 (8) | 0.136 (10) | 0.075 (7) | 0.015 (8) | 0.003 (7) | 0.013 (7) |
O4 | 0.054 (6) | 0.143 (11) | 0.119 (9) | −0.028 (6) | −0.004 (6) | 0.007 (8) |
O5 | 0.056 (6) | 0.090 (7) | 0.075 (6) | 0.012 (5) | 0.005 (5) | −0.003 (5) |
O6 | 0.071 (6) | 0.072 (7) | 0.071 (6) | 0.017 (5) | −0.003 (5) | 0.005 (5) |
O7 | 0.067 (6) | 0.070 (6) | 0.066 (6) | −0.001 (5) | 0.024 (5) | 0.005 (5) |
O8 | 0.161 (12) | 0.097 (8) | 0.095 (8) | 0.006 (8) | 0.050 (8) | 0.018 (7) |
O11 | 0.123 (9) | 0.093 (8) | 0.087 (8) | −0.006 (7) | 0.001 (7) | 0.002 (6) |
O12 | 0.057 (5) | 0.063 (6) | 0.058 (5) | 0.004 (4) | 0.023 (4) | 0.003 (4) |
C3 | 0.100 (13) | 0.106 (13) | 0.107 (14) | −0.016 (11) | −0.022 (12) | −0.015 (12) |
C4 | 0.099 (13) | 0.115 (14) | 0.074 (11) | 0.008 (12) | −0.024 (10) | −0.017 (10) |
C5 | 0.082 (10) | 0.132 (12) | 0.063 (10) | 0.028 (7) | −0.002 (8) | −0.013 (9) |
C6 | 0.167 (14) | 0.097 (11) | 0.117 (16) | 0.021 (11) | −0.003 (13) | −0.021 (10) |
C7 | 0.141 (15) | 0.191 (17) | 0.075 (12) | 0.099 (12) | −0.016 (13) | −0.021 (14) |
C8 | 0.126 (16) | 0.25 (3) | 0.120 (18) | 0.046 (12) | −0.031 (14) | −0.076 (18) |
C9 | 0.097 (11) | 0.227 (19) | 0.075 (12) | −0.007 (12) | −0.014 (9) | −0.028 (13) |
C10 | 0.103 (11) | 0.136 (13) | 0.075 (11) | 0.000 (10) | −0.008 (9) | −0.005 (10) |
C11 | 0.033 (8) | 0.37 (4) | 0.071 (11) | 0.054 (16) | −0.018 (7) | −0.064 (19) |
C12 | 0.16 (2) | 0.082 (16) | 0.21 (3) | 0.065 (15) | 0.10 (2) | 0.054 (16) |
C13 | 0.090 (12) | 0.122 (14) | 0.090 (12) | 0.023 (11) | −0.015 (9) | 0.042 (10) |
C14 | 0.078 (11) | 0.069 (11) | 0.109 (13) | −0.002 (9) | 0.034 (10) | 0.031 (10) |
C15 | 0.048 (8) | 0.137 (14) | 0.094 (10) | −0.015 (8) | −0.029 (7) | −0.057 (10) |
C16 | 0.107 (13) | 0.051 (10) | 0.23 (2) | −0.006 (9) | 0.102 (14) | 0.001 (11) |
C17 | 0.077 (11) | 0.133 (15) | 0.099 (12) | 0.004 (10) | 0.018 (10) | 0.022 (12) |
C18 | 0.069 (11) | 0.107 (13) | 0.102 (13) | −0.003 (9) | 0.002 (10) | 0.009 (10) |
C19 | 0.082 (10) | 0.093 (12) | 0.091 (11) | 0.013 (9) | −0.006 (9) | 0.031 (9) |
C20 | 0.103 (12) | 0.068 (10) | 0.081 (11) | 0.039 (9) | 0.009 (9) | 0.009 (8) |
C21 | 0.096 (11) | 0.086 (12) | 0.080 (11) | 0.000 (9) | 0.051 (9) | 0.004 (9) |
C22 | 0.142 (16) | 0.090 (14) | 0.118 (15) | 0.007 (12) | 0.077 (12) | 0.010 (11) |
C23 | 0.167 (18) | 0.099 (13) | 0.108 (14) | 0.010 (12) | 0.057 (13) | −0.009 (11) |
C25 | 0.094 (11) | 0.060 (9) | 0.153 (16) | 0.003 (8) | −0.041 (11) | −0.018 (9) |
C29 | 0.084 (11) | 0.072 (10) | 0.132 (15) | 0.007 (9) | 0.049 (10) | −0.023 (10) |
C31 | 0.042 (8) | 0.114 (14) | 0.072 (10) | 0.013 (9) | −0.009 (8) | −0.021 (10) |
C32 | 0.036 (8) | 0.100 (13) | 0.087 (11) | 0.001 (8) | 0.003 (8) | 0.011 (10) |
C33 | 0.054 (9) | 0.124 (15) | 0.066 (10) | 0.012 (9) | 0.016 (8) | 0.019 (10) |
C34 | 0.088 (12) | 0.105 (13) | 0.101 (13) | 0.029 (11) | −0.007 (11) | −0.011 (11) |
C35 | 0.055 (9) | 0.135 (16) | 0.073 (11) | 0.011 (10) | 0.003 (8) | 0.018 (11) |
C36 | 0.055 (9) | 0.098 (12) | 0.059 (9) | −0.007 (8) | 0.006 (7) | 0.013 (9) |
C37 | 0.066 (9) | 0.132 (14) | 0.058 (9) | 0.007 (10) | 0.004 (7) | 0.006 (9) |
C38 | 0.070 (10) | 0.070 (10) | 0.058 (9) | −0.001 (8) | 0.016 (8) | −0.010 (8) |
C39 | 0.061 (9) | 0.075 (10) | 0.058 (9) | −0.018 (8) | 0.020 (7) | −0.008 (8) |
C40 | 0.036 (7) | 0.069 (9) | 0.061 (8) | −0.001 (7) | 0.012 (7) | −0.005 (7) |
C41 | 0.070 (10) | 0.070 (11) | 0.091 (11) | −0.004 (8) | 0.038 (8) | 0.000 (9) |
C42 | 0.084 (11) | 0.060 (10) | 0.112 (13) | −0.025 (9) | 0.025 (10) | −0.035 (10) |
C43 | 0.057 (9) | 0.117 (16) | 0.065 (10) | −0.011 (10) | 0.020 (8) | −0.018 (10) |
C44 | 0.041 (7) | 0.077 (9) | 0.083 (9) | −0.006 (7) | 0.021 (7) | 0.012 (8) |
C45 | 0.031 (7) | 0.083 (10) | 0.068 (9) | 0.006 (7) | 0.001 (6) | −0.025 (8) |
C46 | 0.047 (7) | 0.062 (9) | 0.048 (8) | 0.012 (7) | 0.004 (6) | 0.008 (7) |
C47 | 0.056 (8) | 0.062 (9) | 0.066 (9) | 0.012 (7) | 0.000 (7) | −0.018 (7) |
C48 | 0.065 (9) | 0.085 (12) | 0.063 (9) | 0.000 (9) | 0.001 (8) | −0.016 (9) |
C49 | 0.082 (10) | 0.055 (9) | 0.088 (11) | 0.017 (8) | −0.010 (9) | −0.014 (9) |
C50 | 0.068 (9) | 0.058 (10) | 0.090 (11) | −0.005 (8) | 0.001 (8) | −0.019 (8) |
C51 | 0.090 (11) | 0.073 (10) | 0.068 (9) | 0.041 (9) | 0.022 (9) | 0.028 (8) |
C52 | 0.076 (10) | 0.066 (10) | 0.048 (8) | 0.002 (9) | 0.020 (7) | 0.001 (7) |
C53 | 0.076 (10) | 0.045 (8) | 0.066 (9) | −0.008 (8) | 0.033 (8) | −0.007 (7) |
C54 | 0.061 (9) | 0.070 (11) | 0.089 (11) | −0.013 (8) | 0.036 (9) | −0.008 (9) |
C55 | 0.069 (11) | 0.081 (12) | 0.092 (11) | −0.015 (9) | 0.039 (9) | −0.023 (9) |
C56 | 0.094 (13) | 0.049 (9) | 0.140 (16) | −0.024 (10) | 0.013 (11) | −0.022 (10) |
C57 | 0.118 (15) | 0.080 (13) | 0.104 (13) | 0.026 (12) | 0.064 (12) | 0.030 (11) |
C58 | 0.045 (9) | 0.110 (12) | 0.098 (12) | −0.008 (9) | 0.012 (8) | −0.022 (10) |
Geometric parameters (Å, º) top
O1—C31 | 1.38 (2) | C13—C14 | 1.363 (10) |
O1—C1A | 1.432 (11) | C14—C15 | 1.356 (10) |
O1—C1B | 1.441 (11) | C15—C16 | 1.318 (9) |
O2—C2B | 1.419 (11) | C17—C18 | 1.50 (2) |
O2—C3 | 1.424 (10) | C19—C20 | 1.52 (2) |
O2—C2A | 1.429 (11) | C21—C22 | 1.47 (2) |
O3—C5 | 1.405 (10) | C23—C24A | 1.485 (11) |
O3—C4 | 1.420 (10) | C23—C24B | 1.570 (11) |
O4—C14 | 1.379 (10) | C25—C26B | 1.515 (11) |
O4—C17 | 1.420 (10) | C25—C26A | 1.529 (11) |
O5—C18 | 1.39 (2) | C27A—C28A | 1.530 (11) |
O5—C19 | 1.43 (2) | C27B—C28B | 1.531 (11) |
O6—C46 | 1.392 (14) | C29—C30B | 1.516 (12) |
O6—C20 | 1.42 (2) | C29—C30A | 1.550 (11) |
O7—C39 | 1.39 (2) | C31—C32 | 1.40 (2) |
O7—C21 | 1.408 (15) | C31—C36 | 1.38 (2) |
O8—C22 | 1.412 (10) | C32—C33 | 1.36 (2) |
O8—C23 | 1.411 (9) | C32—C58 | 1.51 (2) |
O9A—C25 | 1.410 (10) | C33—C34 | 1.37 (2) |
O9A—C24A | 1.451 (11) | C34—C35 | 1.41 (2) |
O9B—C24B | 1.413 (11) | C35—C36 | 1.33 (2) |
O9B—C25 | 1.450 (10) | C36—C37 | 1.53 (2) |
O10A—C27A | 1.430 (11) | C37—C38 | 1.54 (2) |
O10A—C26A | 1.413 (11) | C38—C39 | 1.38 (2) |
O10B—C27B | 1.418 (11) | C38—C43 | 1.40 (2) |
O10B—C26B | 1.429 (12) | C39—C40 | 1.38 (2) |
O11—C28A | 1.414 (11) | C40—C41 | 1.40 (2) |
O11—C29 | 1.422 (10) | C40—C44 | 1.50 (2) |
O11—C28B | 1.431 (11) | C41—C42 | 1.34 (2) |
O12—C53 | 1.386 (14) | C42—C43 | 1.39 (2) |
O12—C30B | 1.428 (11) | C44—C45 | 1.53 (2) |
O12—C30A | 1.440 (11) | C45—C50 | 1.37 (2) |
N1—N2 | 1.08 | C45—C46 | 1.39 (2) |
N1—C8 | 1.431 (14) | C46—C47 | 1.36 (2) |
N2—C11 | 1.358 (8) | C47—C48 | 1.37 (2) |
C1A—C2A | 1.529 (11) | C47—C51 | 1.55 (2) |
C1B—C2B | 1.529 (11) | C48—C49 | 1.37 (2) |
C3—C4 | 1.524 (10) | C49—C50 | 1.38 (2) |
C5—C10 | 1.392 (10) | C51—C52 | 1.48 (2) |
C5—C6 | 1.41 (2) | C52—C53 | 1.39 (2) |
C6—C7 | 1.423 (10) | C52—C57 | 1.41 (2) |
C7—C8 | 1.357 (11) | C53—C54 | 1.40 (2) |
C8—C9 | 1.364 (11) | C54—C55 | 1.38 (2) |
C9—C10 | 1.385 (10) | C54—C58 | 1.51 (2) |
C11—C12 | 1.381 (9) | C55—C56 | 1.36 (2) |
C11—C16 | 1.390 (9) | C56—C57 | 1.37 (2) |
C12—C13 | 1.335 (10) | | |
| | | |
C31—O1—C1A | 127.1 (16) | O10A—C27A—C28A | 108.1 (10) |
C31—O1—C1B | 97.6 (16) | O10B—C27B—C28B | 108.3 (11) |
C2B—O2—C3 | 115.3 (19) | O11—C28A—C27A | 106.5 (18) |
C3—O2—C2A | 101.4 (14) | O11—C28B—C27B | 102.4 (16) |
C5—O3—C4 | 117.1 (12) | O11—C29—C30B | 109.8 (11) |
C14—O4—C17 | 116.4 (12) | O11—C29—C30A | 106.0 (10) |
C18—O5—C19 | 113.8 (11) | O12—C30A—C29 | 107.0 (11) |
C46—O6—C20 | 112.6 (10) | O12—C30B—C29 | 109.4 (12) |
C39—O7—C21 | 115.2 (10) | O1—C31—C32 | 118.7 (16) |
C22—O8—C23 | 116.5 (12) | O1—C31—C36 | 119.3 (14) |
C25—O9A—C24A | 103.8 (11) | C32—C31—C36 | 121.9 (17) |
C24B—O9B—C25 | 129 (3) | C33—C32—C31 | 117.7 (15) |
C27A—O10A—C26A | 119 (2) | C33—C32—C58 | 117.7 (15) |
C27B—O10B—C26B | 112 (2) | C31—C32—C58 | 124.2 (17) |
C28A—O11—C29 | 113.7 (17) | C32—C33—C34 | 120.9 (15) |
C29—O11—C28B | 111.9 (13) | C33—C34—C35 | 119.7 (17) |
C53—O12—C30B | 114.9 (8) | C36—C35—C34 | 120.7 (17) |
C53—O12—C30A | 114.8 (8) | C35—C36—C31 | 118.8 (15) |
N2—N1—C8 | 130.6 (6) | C35—C36—C37 | 122.1 (14) |
N1—N2—C11 | 147.2 (6) | C31—C36—C37 | 119.0 (16) |
O1—C1A—C2A | 106.3 (18) | C36—C37—C38 | 110.0 (11) |
O1—C1B—C2B | 112 (2) | C39—C38—C43 | 118.4 (14) |
O2—C2A—C1A | 107.6 (18) | C39—C38—C37 | 124.2 (14) |
O2—C2B—C1B | 105 (2) | C43—C38—C37 | 117.3 (15) |
O2—C3—C4 | 105.4 (12) | C38—C39—C40 | 122.0 (13) |
O3—C4—C3 | 109.6 (13) | C38—C39—O7 | 118.3 (14) |
C10—C5—C6 | 117.7 (13) | C40—C39—O7 | 119.7 (12) |
C10—C5—O3 | 109.0 (12) | C39—C40—C41 | 118.0 (13) |
C6—C5—O3 | 133.3 (14) | C39—C40—C44 | 120.1 (12) |
C5—C6—C7 | 116.0 (16) | C41—C40—C44 | 121.3 (13) |
C8—C7—C6 | 129.4 (18) | C42—C41—C40 | 120.8 (15) |
C9—C8—C7 | 109.3 (18) | C41—C42—C43 | 121.3 (15) |
C9—C8—N1 | 117.3 (11) | C42—C43—C38 | 119.1 (14) |
C7—C8—N1 | 131.6 (14) | C40—C44—C45 | 110.1 (9) |
C8—C9—C10 | 128.6 (19) | C50—C45—C46 | 117.4 (12) |
C5—C10—C9 | 118.8 (17) | C50—C45—C44 | 121.5 (13) |
N2—C11—C12 | 123.2 (9) | C46—C45—C44 | 120.9 (12) |
N2—C11—C16 | 113.2 (9) | C47—C46—C45 | 122.4 (12) |
C12—C11—C16 | 123.6 (9) | C47—C46—O6 | 120.1 (11) |
C11—C12—C13 | 119.1 (13) | C45—C46—O6 | 117.5 (11) |
C12—C13—C14 | 111.6 (14) | C48—C47—C46 | 118.9 (13) |
C15—C14—C13 | 133.8 (14) | C48—C47—C51 | 118.6 (12) |
C15—C14—O4 | 107.7 (12) | C46—C47—C51 | 121.2 (12) |
C13—C14—O4 | 118.5 (13) | C47—C48—C49 | 120.3 (14) |
C14—C15—C16 | 112.1 (13) | C50—C49—C48 | 119.7 (13) |
C15—C16—C11 | 119.5 (11) | C45—C50—C49 | 120.8 (14) |
O4—C17—C18 | 108.0 (13) | C52—C51—C47 | 114.3 (11) |
O5—C18—C17 | 109.6 (13) | C53—C52—C57 | 117.2 (16) |
O5—C19—C20 | 115.6 (12) | C53—C52—C51 | 120.1 (13) |
O6—C20—C19 | 110.4 (12) | C57—C52—C51 | 122.4 (16) |
O7—C21—C22 | 109.9 (12) | C52—C53—O12 | 120.3 (13) |
O8—C22—C21 | 114.1 (14) | C52—C53—C54 | 122.1 (13) |
O8—C23—C24A | 114.8 (9) | O12—C53—C54 | 117.6 (14) |
O8—C23—C24B | 103.5 (9) | C55—C54—C53 | 117.0 (15) |
O9A—C24A—C23 | 105.8 (10) | C55—C54—C58 | 122.0 (16) |
O9B—C24B—C23 | 109.8 (11) | C53—C54—C58 | 120.6 (13) |
O9B—C25—C26B | 107.0 (19) | C56—C55—C54 | 123.2 (16) |
O9A—C25—C26A | 102.0 (13) | C55—C56—C57 | 118.9 (15) |
O10A—C26A—C25 | 110.3 (11) | C56—C57—C52 | 121.5 (17) |
O10B—C26B—C25 | 107.9 (11) | C54—C58—C32 | 109.3 (11) |
Crystal data top
C58H64N2O12 | F(000) = 2088 |
Mr = 981.11 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.341 (6) Å | Cell parameters from 25 reflections |
b = 11.709 (3) Å | θ = 8–12° |
c = 23.875 (8) Å | µ = 0.09 mm−1 |
β = 112.39 (2)° | T = 273 K |
V = 5258 (3) Å3 | Parallelepipedic, orange |
Z = 4 | 0.65 × 0.60 × 0.50 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 23°, θmin = 1° |
Graphite monochromator | h = 0→22 |
ω/θ scans | k = 0→12 |
7559 measured reflections | l = −26→24 |
7304 independent reflections | 3 standard reflections every 60 min |
3495 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.107 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.367 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1516P)2 + 13.1365P], where P = (Fo2 + 2Fc2)/3 |
5696 reflections | (Δ/σ)max = 0.016 |
636 parameters | Δρmax = 0.56 e Å−3 |
75 restraints | Δρmin = −0.33 e Å−3 |
Crystal data top
C58H64N2O12 | V = 5258 (3) Å3 |
Mr = 981.11 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 20.341 (6) Å | µ = 0.09 mm−1 |
b = 11.709 (3) Å | T = 273 K |
c = 23.875 (8) Å | 0.65 × 0.60 × 0.50 mm |
β = 112.39 (2)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.017 |
7559 measured reflections | θmax = 23° |
7304 independent reflections | 3 standard reflections every 60 min |
3495 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement top
R[F2 > 2σ(F2)] = 0.107 | 75 restraints |
wR(F2) = 0.367 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.56 e Å−3 |
5696 reflections | Δρmin = −0.33 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.3167 (3) | −0.0297 (6) | 0.2072 (4) | 0.091 (2) | |
O2A | 0.4558 (7) | −0.1238 (14) | 0.2473 (6) | 0.106 (6)* | 0.60 (2) |
O2B | 0.4626 (6) | −0.2055 (14) | 0.2264 (6) | 0.071 (7)* | 0.41 (2) |
O3 | 0.5656 (4) | −0.1722 (9) | 0.3615 (3) | 0.123 (3) | |
O4 | 0.0827 (3) | 0.0301 (7) | 0.4923 (3) | 0.082 (2) | |
O5 | 0.0782 (3) | 0.1844 (7) | 0.3959 (3) | 0.081 (2) | |
O6 | 0.1708 (3) | 0.2595 (6) | 0.3354 (3) | 0.075 (2) | |
O7 | 0.0690 (3) | 0.0999 (6) | 0.1302 (3) | 0.076 (2) | |
O8 | −0.0186 (6) | 0.1624 (8) | 0.0068 (4) | 0.147 (4) | |
O9A | 0.0927 (8) | 0.3541 (13) | −0.0315 (8) | 0.151 (7)* | 0.70 (2) |
O9B | 0.0734 (15) | 0.421 (2) | 0.0017 (11) | 0.132 (9)* | 0.31 (2) |
O10A | 0.1970 (9) | 0.5125 (17) | 0.0310 (11) | 0.163 (14)* | 0.66 (3) |
O10B | 0.2089 (10) | 0.5104 (18) | 0.0159 (5) | 0.158 (15)* | 0.35 (3) |
O11A | 0.3324 (10) | 0.5120 (14) | 0.1411 (4) | 0.168 (15)* | 0.66 (3) |
O11B | 0.3068 (9) | 0.5984 (12) | 0.1668 (6) | 0.145 (16)* | 0.35 (3) |
O12 | 0.3240 (4) | 0.3892 (6) | 0.2354 (3) | 0.076 (2) | |
N1 | 0.3329 (4) | −0.1618 (7) | 0.4297 (3) | 0.060 (2) | |
N2 | 0.3332 (4) | −0.0801 (7) | 0.4636 (3) | 0.059 (2) | |
C1A | 0.3349 (7) | −0.1239 (17) | 0.1763 (10) | 0.120 (11)* | 0.60 (2) |
C1B | 0.3456 (8) | −0.1352 (13) | 0.1990 (14) | 0.068 (9)* | 0.41 (2) |
C2A | 0.4124 (7) | −0.114 (3) | 0.1848 (7) | 0.16 (2)* | 0.60 (2) |
C2B | 0.4208 (12) | −0.110 (2) | 0.2004 (18) | 0.14 (2)* | 0.41 (2) |
C3A | 0.5302 (7) | −0.131 (2) | 0.2565 (6) | 0.113 (9)* | 0.60 (2) |
C3B | 0.5366 (8) | −0.184 (2) | 0.2539 (5) | 0.081 (9)* | 0.41 (2) |
C4A | 0.5631 (9) | −0.2196 (19) | 0.3074 (6) | 0.159 (8)* | 0.60 (2) |
C4B | 0.5655 (10) | −0.2481 (19) | 0.3148 (6) | 0.154 (10)* | 0.41 (2) |
C5 | 0.5084 (6) | −0.1825 (10) | 0.3780 (5) | 0.075 (3) | |
C6 | 0.4487 (7) | −0.2472 (11) | 0.3525 (6) | 0.097 (4) | |
H6 | 0.4455 (7) | −0.2959 (11) | 0.3208 (6) | 0.116* | |
C7 | 0.3933 (6) | −0.2435 (11) | 0.3715 (5) | 0.084 (3) | |
H7 | 0.3538 (6) | −0.2897 (11) | 0.3528 (5) | 0.101* | |
C8 | 0.3954 (5) | −0.1734 (8) | 0.4172 (5) | 0.061 (2) | |
C9 | 0.4561 (5) | −0.1101 (10) | 0.4454 (5) | 0.084 (3) | |
H9 | 0.4587 (5) | −0.0620 (10) | 0.4772 (5) | 0.101* | |
C10 | 0.5123 (6) | −0.1158 (10) | 0.4282 (6) | 0.083 (3) | |
H10 | 0.5536 (6) | −0.0754 (10) | 0.4496 (6) | 0.100* | |
C11 | 0.2680 (4) | −0.0635 (8) | 0.4719 (4) | 0.053 (2) | |
C12 | 0.2108 (5) | −0.1335 (8) | 0.4503 (4) | 0.059 (2) | |
H12 | 0.2129 (5) | −0.2013 (8) | 0.4308 (4) | 0.070* | |
C13 | 0.1491 (5) | −0.1021 (10) | 0.4580 (4) | 0.071 (3) | |
H13 | 0.1100 (5) | −0.1505 (10) | 0.4439 (4) | 0.085* | |
C14 | 0.1441 (5) | −0.0019 (10) | 0.4855 (4) | 0.062 (3) | |
C15 | 0.2037 (5) | 0.0654 (10) | 0.5100 (4) | 0.071 (3) | |
H15 | 0.2020 (5) | 0.1311 (10) | 0.5313 (4) | 0.086* | |
C16 | 0.2655 (4) | 0.0368 (8) | 0.5035 (4) | 0.062 (2) | |
H16 | 0.3054 (4) | 0.0830 (8) | 0.5197 (4) | 0.075* | |
C17 | 0.0241 (5) | 0.0472 (11) | 0.4367 (6) | 0.101 (4) | |
H17A | −0.0197 (5) | 0.0286 (11) | 0.4420 (6) | 0.121* | |
H17B | 0.0283 (5) | −0.0038 (11) | 0.4062 (6) | 0.121* | |
C18 | 0.0205 (5) | 0.1690 (11) | 0.4150 (5) | 0.091 (4) | |
H18A | −0.0243 (5) | 0.1829 (11) | 0.3816 (5) | 0.109* | |
H18B | 0.0246 (5) | 0.2216 (11) | 0.4475 (5) | 0.109* | |
C19 | 0.0875 (5) | 0.3014 (12) | 0.3845 (5) | 0.086 (3) | |
H19A | 0.0811 (5) | 0.3487 (12) | 0.4154 (5) | 0.103* | |
H19B | 0.0522 (5) | 0.3236 (12) | 0.3455 (5) | 0.103* | |
C20 | 0.1610 (5) | 0.3194 (12) | 0.3848 (5) | 0.098 (4) | |
H20A | 0.1689 (5) | 0.4005 (12) | 0.3815 (5) | 0.118* | |
H20B | 0.1960 (5) | 0.2927 (12) | 0.4230 (5) | 0.118* | |
C21 | 0.0046 (6) | 0.0458 (12) | 0.0931 (5) | 0.105 (5) | |
H21A | −0.0185 (6) | 0.0133 (12) | 0.1182 (5) | 0.126* | |
H21B | 0.0148 (6) | −0.0157 (12) | 0.0704 (5) | 0.126* | |
C22 | −0.0442 (6) | 0.1322 (12) | 0.0498 (6) | 0.141 (7) | |
H22A | −0.0913 (6) | 0.0997 (12) | 0.0305 (6) | 0.169* | |
H22B | −0.0479 (6) | 0.1995 (12) | 0.0721 (6) | 0.169* | |
C23A | 0.0147 (17) | 0.2701 (19) | 0.0122 (11) | 0.179 (11)* | 0.70 (2) |
C23B | 0.0385 (11) | 0.241 (2) | 0.0258 (13) | 0.164 (14)* | 0.31 (2) |
C24A | 0.0270 (12) | 0.2939 (18) | −0.0464 (8) | 0.159 (11)* | 0.70 (2) |
C24B | 0.0148 (12) | 0.344 (2) | −0.0179 (19) | 0.176 (12)* | 0.31 (2) |
C25 | 0.0855 (7) | 0.4674 (13) | −0.0481 (8) | 0.214 (8) | |
C26 | 0.1466 (8) | 0.5424 (14) | −0.0285 (7) | 0.224 (9) | |
C27 | 0.2395 (5) | 0.6023 (12) | 0.0604 (4) | 0.292 (16) | |
C28A | 0.3183 | 0.5826 | 0.0897 | 0.150* | 0.50 |
C28B | 0.2576 | 0.5343 | 0.1208 | 0.150* | 0.50 |
C29 | 0.3737 (6) | 0.5546 (13) | 0.1965 (4) | 0.206 (11) | |
C30 | 0.3779 (7) | 0.4741 (10) | 0.2474 (4) | 0.126 (5) | |
H30A | 0.4235 (7) | 0.4354 (10) | 0.2605 (4) | 0.151* | |
H30B | 0.3777 (7) | 0.5199 (10) | 0.2812 (4) | 0.151* | |
C31 | 0.2842 (5) | 0.0512 (8) | 0.1631 (4) | 0.061 (2) | |
C32 | 0.2170 (5) | 0.0314 (9) | 0.1213 (4) | 0.067 (3) | |
C33 | 0.1877 (7) | 0.1134 (12) | 0.0763 (5) | 0.088 (3) | |
H33 | 0.1427 (7) | 0.1025 (12) | 0.0465 (5) | 0.105* | |
C34 | 0.2261 (9) | 0.2118 (13) | 0.0763 (6) | 0.108 (5) | |
H34 | 0.2083 (9) | 0.2632 (13) | 0.0443 (6) | 0.130* | |
C35 | 0.2876 (7) | 0.2334 (11) | 0.1211 (6) | 0.087 (3) | |
H35 | 0.3092 (7) | 0.3039 (11) | 0.1224 (6) | 0.105* | |
C36 | 0.3204 (6) | 0.1552 (10) | 0.1657 (5) | 0.079 (3) | |
C37 | 0.3863 (5) | 0.1821 (10) | 0.2209 (5) | 0.085 (3) | |
H37A | 0.4100 (5) | 0.2476 (10) | 0.2122 (5) | 0.102* | |
H37B | 0.4186 (5) | 0.1177 (10) | 0.2295 (5) | 0.102* | |
C38 | 0.3698 (5) | 0.2078 (10) | 0.2769 (5) | 0.071 (3) | |
C39 | 0.3377 (5) | 0.3079 (10) | 0.2805 (5) | 0.068 (3) | |
C40 | 0.3158 (5) | 0.3278 (10) | 0.3282 (5) | 0.073 (3) | |
C41 | 0.3306 (6) | 0.2453 (13) | 0.3733 (5) | 0.086 (4) | |
H41 | 0.3171 (6) | 0.2569 (13) | 0.4059 (5) | 0.103* | |
C42 | 0.3648 (6) | 0.1487 (14) | 0.3697 (7) | 0.100 (4) | |
H42 | 0.3759 (6) | 0.0955 (14) | 0.4008 (7) | 0.120* | |
C43 | 0.3827 (6) | 0.1277 (11) | 0.3232 (6) | 0.087 (3) | |
H43 | 0.4043 (6) | 0.0586 (11) | 0.3212 (6) | 0.104* | |
C44 | 0.2687 (6) | 0.4296 (10) | 0.3267 (5) | 0.084 (3) | |
H44A | 0.2893 (6) | 0.4986 (10) | 0.3179 (5) | 0.101* | |
H44B | 0.2655 (6) | 0.4386 (10) | 0.3660 (5) | 0.101* | |
C45 | 0.1947 (6) | 0.4117 (10) | 0.2785 (5) | 0.071 (3) | |
C46 | 0.1509 (5) | 0.3218 (9) | 0.2822 (4) | 0.066 (3) | |
C47 | 0.0911 (5) | 0.2884 (9) | 0.2332 (4) | 0.064 (3) | |
C48 | 0.0707 (6) | 0.3515 (12) | 0.1818 (5) | 0.082 (3) | |
H48 | 0.0300 (6) | 0.3306 (12) | 0.1490 (5) | 0.098* | |
C49 | 0.1081 (8) | 0.4443 (12) | 0.1768 (6) | 0.095 (4) | |
H49 | 0.0916 (8) | 0.4885 (12) | 0.1418 (6) | 0.114* | |
C50 | 0.1715 (7) | 0.4733 (11) | 0.2246 (7) | 0.092 (4) | |
H50 | 0.1984 (7) | 0.5343 (11) | 0.2202 (7) | 0.111* | |
C51 | 0.0543 (5) | 0.1772 (11) | 0.2360 (5) | 0.081 (3) | |
H51A | 0.0429 (5) | 0.1775 (11) | 0.2719 (5) | 0.097* | |
H51B | 0.0099 (5) | 0.1727 (11) | 0.2010 (5) | 0.097* | |
C52 | 0.0979 (5) | 0.0730 (10) | 0.2372 (5) | 0.067 (3) | |
C53 | 0.1070 (5) | 0.0405 (9) | 0.1838 (5) | 0.068 (3) | |
C54 | 0.1533 (5) | −0.0470 (9) | 0.1822 (5) | 0.068 (3) | |
C55 | 0.1882 (6) | −0.1023 (10) | 0.2363 (6) | 0.087 (3) | |
H55 | 0.2197 (6) | −0.1609 (10) | 0.2376 (6) | 0.104* | |
C56 | 0.1783 (8) | −0.0744 (12) | 0.2879 (6) | 0.102 (4) | |
H56 | 0.2007 (8) | −0.1172 (12) | 0.3228 (6) | 0.122* | |
C57 | 0.1362 (6) | 0.0151 (12) | 0.2892 (5) | 0.084 (3) | |
H57 | 0.1334 (6) | 0.0370 (12) | 0.3257 (5) | 0.101* | |
C58 | 0.1720 (5) | −0.0689 (9) | 0.1279 (5) | 0.078 (3) | |
H58A | 0.1291 (5) | −0.0757 (9) | 0.0918 (5) | 0.094* | |
H58B | 0.1986 (5) | −0.1395 (9) | 0.1333 (5) | 0.094* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.069 (4) | 0.069 (5) | 0.115 (6) | 0.000 (4) | 0.012 (4) | 0.018 (5) |
O3 | 0.060 (5) | 0.206 (10) | 0.102 (6) | 0.032 (6) | 0.032 (4) | −0.024 (6) |
O4 | 0.050 (4) | 0.134 (7) | 0.063 (4) | 0.004 (4) | 0.025 (3) | 0.010 (4) |
O5 | 0.065 (4) | 0.109 (6) | 0.086 (5) | 0.011 (4) | 0.049 (4) | 0.018 (4) |
O6 | 0.071 (4) | 0.104 (6) | 0.050 (4) | −0.029 (4) | 0.023 (3) | −0.009 (4) |
O7 | 0.054 (4) | 0.096 (5) | 0.063 (4) | 0.006 (4) | 0.006 (3) | −0.010 (4) |
O8 | 0.172 (11) | 0.137 (9) | 0.089 (6) | 0.015 (8) | 0.000 (7) | −0.006 (7) |
O12 | 0.080 (5) | 0.057 (4) | 0.093 (5) | −0.021 (4) | 0.037 (4) | −0.003 (4) |
N1 | 0.057 (5) | 0.057 (5) | 0.063 (5) | −0.001 (4) | 0.020 (4) | 0.006 (4) |
N2 | 0.055 (5) | 0.056 (5) | 0.057 (5) | 0.006 (4) | 0.012 (4) | 0.009 (4) |
C5 | 0.065 (7) | 0.096 (9) | 0.074 (7) | 0.027 (6) | 0.036 (6) | 0.025 (7) |
C6 | 0.100 (9) | 0.102 (10) | 0.107 (9) | 0.013 (8) | 0.061 (8) | −0.016 (8) |
C7 | 0.070 (7) | 0.103 (9) | 0.085 (8) | −0.015 (6) | 0.036 (6) | −0.024 (7) |
C8 | 0.050 (6) | 0.058 (6) | 0.075 (6) | 0.007 (5) | 0.022 (5) | −0.005 (5) |
C9 | 0.054 (6) | 0.102 (9) | 0.100 (8) | 0.016 (6) | 0.033 (6) | −0.034 (7) |
C10 | 0.063 (6) | 0.082 (8) | 0.111 (9) | 0.001 (6) | 0.041 (6) | −0.004 (7) |
C11 | 0.042 (5) | 0.065 (6) | 0.051 (5) | 0.002 (4) | 0.016 (4) | 0.003 (5) |
C12 | 0.052 (5) | 0.060 (6) | 0.059 (6) | −0.010 (5) | 0.015 (4) | 0.000 (5) |
C13 | 0.053 (6) | 0.090 (8) | 0.070 (6) | −0.022 (6) | 0.023 (5) | 0.000 (6) |
C14 | 0.052 (6) | 0.081 (8) | 0.050 (5) | 0.004 (5) | 0.017 (5) | 0.013 (5) |
C15 | 0.058 (6) | 0.089 (8) | 0.074 (6) | 0.009 (6) | 0.033 (5) | 0.002 (6) |
C16 | 0.044 (5) | 0.066 (7) | 0.074 (6) | −0.004 (5) | 0.020 (5) | −0.013 (5) |
C17 | 0.043 (6) | 0.152 (13) | 0.119 (10) | 0.005 (7) | 0.044 (7) | 0.035 (9) |
C18 | 0.058 (6) | 0.149 (12) | 0.065 (7) | 0.005 (7) | 0.025 (5) | 0.011 (8) |
C19 | 0.091 (8) | 0.114 (11) | 0.061 (6) | 0.001 (7) | 0.038 (6) | −0.011 (7) |
C20 | 0.085 (8) | 0.148 (12) | 0.067 (7) | −0.043 (8) | 0.036 (6) | −0.023 (8) |
C21 | 0.064 (7) | 0.180 (14) | 0.063 (7) | −0.011 (8) | 0.017 (6) | −0.032 (8) |
C22 | 0.083 (9) | 0.218 (19) | 0.073 (9) | 0.020 (11) | −0.025 (8) | −0.045 (11) |
C25 | 0.177 (17) | 0.174 (18) | 0.29 (2) | 0.020 (12) | 0.085 (17) | 0.047 (16) |
C26 | 0.158 (17) | 0.193 (18) | 0.30 (2) | 0.025 (13) | 0.070 (18) | 0.040 (17) |
C27 | 0.41 (4) | 0.34 (4) | 0.17 (2) | 0.07 (4) | 0.16 (3) | 0.10 (3) |
C29 | 0.28 (3) | 0.074 (10) | 0.37 (3) | −0.059 (14) | 0.24 (3) | 0.007 (16) |
C30 | 0.132 (12) | 0.091 (10) | 0.183 (15) | −0.074 (9) | 0.093 (11) | −0.046 (10) |
C31 | 0.056 (6) | 0.059 (6) | 0.064 (6) | 0.012 (5) | 0.017 (5) | 0.011 (5) |
C32 | 0.068 (6) | 0.073 (7) | 0.061 (6) | 0.010 (6) | 0.025 (5) | −0.009 (6) |
C33 | 0.096 (8) | 0.107 (10) | 0.060 (7) | 0.025 (8) | 0.030 (6) | 0.000 (7) |
C34 | 0.148 (14) | 0.105 (11) | 0.076 (9) | 0.029 (10) | 0.047 (10) | 0.039 (8) |
C35 | 0.101 (9) | 0.077 (8) | 0.086 (8) | 0.008 (7) | 0.037 (8) | 0.024 (7) |
C36 | 0.083 (7) | 0.075 (8) | 0.097 (8) | −0.001 (7) | 0.055 (7) | −0.011 (7) |
C37 | 0.058 (6) | 0.077 (8) | 0.114 (9) | −0.019 (6) | 0.026 (6) | −0.009 (7) |
C38 | 0.051 (6) | 0.075 (8) | 0.080 (7) | −0.018 (5) | 0.016 (5) | −0.001 (6) |
C39 | 0.051 (6) | 0.064 (7) | 0.079 (7) | −0.026 (5) | 0.014 (5) | 0.003 (6) |
C40 | 0.056 (6) | 0.083 (8) | 0.079 (7) | −0.029 (6) | 0.023 (5) | 0.000 (7) |
C41 | 0.060 (7) | 0.124 (11) | 0.061 (7) | −0.015 (7) | 0.009 (5) | 0.000 (8) |
C42 | 0.061 (7) | 0.122 (13) | 0.097 (10) | −0.020 (8) | 0.007 (7) | 0.022 (9) |
C43 | 0.059 (7) | 0.092 (9) | 0.091 (8) | −0.003 (6) | 0.007 (6) | 0.020 (8) |
C44 | 0.081 (7) | 0.087 (8) | 0.084 (7) | −0.024 (7) | 0.031 (6) | −0.015 (6) |
C45 | 0.078 (7) | 0.082 (8) | 0.067 (7) | −0.004 (6) | 0.044 (6) | −0.010 (6) |
C46 | 0.069 (6) | 0.086 (8) | 0.050 (6) | 0.009 (6) | 0.031 (5) | −0.001 (6) |
C47 | 0.058 (6) | 0.078 (7) | 0.055 (6) | 0.005 (5) | 0.021 (5) | −0.015 (5) |
C48 | 0.067 (7) | 0.116 (10) | 0.052 (6) | 0.017 (7) | 0.010 (5) | 0.000 (7) |
C49 | 0.112 (10) | 0.097 (10) | 0.073 (8) | 0.023 (9) | 0.031 (8) | 0.014 (7) |
C50 | 0.090 (9) | 0.084 (9) | 0.121 (11) | 0.009 (7) | 0.061 (9) | 0.000 (8) |
C51 | 0.045 (5) | 0.129 (10) | 0.060 (6) | −0.011 (7) | 0.011 (5) | −0.021 (7) |
C52 | 0.051 (5) | 0.089 (8) | 0.063 (6) | −0.025 (5) | 0.023 (5) | −0.025 (6) |
C53 | 0.041 (5) | 0.077 (7) | 0.073 (7) | −0.014 (5) | 0.008 (5) | −0.004 (6) |
C54 | 0.059 (6) | 0.068 (7) | 0.068 (7) | −0.016 (5) | 0.014 (5) | −0.009 (6) |
C55 | 0.087 (8) | 0.071 (8) | 0.096 (9) | −0.006 (6) | 0.027 (7) | 0.010 (7) |
C56 | 0.123 (11) | 0.089 (10) | 0.092 (10) | −0.014 (9) | 0.039 (8) | 0.037 (8) |
C57 | 0.079 (7) | 0.103 (10) | 0.068 (8) | −0.021 (7) | 0.026 (6) | 0.013 (7) |
C58 | 0.057 (6) | 0.081 (8) | 0.086 (7) | −0.010 (5) | 0.016 (5) | −0.029 (6) |
Geometric parameters (Å, º) top
O1—C31 | 1.382 (11) | C11—C12 | 1.354 (12) |
O1—C1B | 1.414 (10) | C11—C16 | 1.407 (12) |
O1—C1A | 1.452 (10) | C12—C13 | 1.384 (13) |
O2A—C2A | 1.420 (10) | C13—C14 | 1.367 (14) |
O2A—C3A | 1.445 (10) | C14—C15 | 1.376 (14) |
O2B—C2B | 1.399 (10) | C15—C16 | 1.365 (12) |
O2B—C3B | 1.416 (10) | C17—C18 | 1.510 (9) |
O3—C5 | 1.369 (11) | C19—C20 | 1.508 (9) |
O3—C4A | 1.388 (10) | C21—C22 | 1.515 (10) |
O3—C4B | 1.426 (10) | C23A—C24A | 1.538 (10) |
O4—C14 | 1.372 (11) | C23B—C24B | 1.544 (11) |
O4—C17 | 1.421 (13) | C25—C26 | 1.446 (8) |
O5—C18 | 1.422 (11) | C27—C28A | 1.502 (10) |
O5—C19 | 1.423 (13) | C27—C28B | 1.563 (9) |
O6—C46 | 1.383 (11) | C29—C30 | 1.515 (9) |
O6—C20 | 1.450 (12) | C31—C32 | 1.372 (13) |
O7—C53 | 1.400 (12) | C31—C36 | 1.412 (14) |
O7—C21 | 1.422 (12) | C32—C33 | 1.394 (15) |
O8—C22 | 1.364 (13) | C32—C58 | 1.532 (14) |
O8—C23A | 1.414 (10) | C33—C34 | 1.39 (2) |
O8—C23B | 1.413 (11) | C34—C35 | 1.33 (2) |
O9A—C25 | 1.377 (10) | C35—C36 | 1.37 (2) |
O9A—C24A | 1.430 (10) | C36—C37 | 1.513 (15) |
O9B—C25 | 1.414 (10) | C37—C38 | 1.53 (2) |
O9B—C24B | 1.426 (11) | C38—C39 | 1.360 (15) |
O10A—C27 | 1.372 (10) | C38—C43 | 1.397 (15) |
O10A—C26 | 1.444 (10) | C39—C40 | 1.391 (15) |
O10B—C26 | 1.359 (10) | C40—C41 | 1.39 (2) |
O10B—C27 | 1.473 (11) | C40—C44 | 1.52 (2) |
O11A—C29 | 1.364 (10) | C41—C42 | 1.35 (2) |
O11A—C28A | 1.414 (9) | C42—C43 | 1.32 (2) |
O11B—C29 | 1.373 (10) | C44—C45 | 1.521 (15) |
O11B—C28B | 1.390 (10) | C45—C50 | 1.39 (2) |
O12—C39 | 1.385 (12) | C45—C46 | 1.404 (14) |
O12—C30 | 1.427 (12) | C46—C47 | 1.384 (13) |
N1—N2 | 1.251 (10) | C47—C48 | 1.356 (15) |
N1—C8 | 1.419 (11) | C47—C51 | 1.516 (14) |
N2—C11 | 1.427 (11) | C48—C49 | 1.36 (2) |
C1A—C2A | 1.515 (10) | C49—C50 | 1.40 (2) |
C1B—C2B | 1.546 (10) | C51—C52 | 1.502 (15) |
C3A—C4A | 1.543 (10) | C52—C57 | 1.368 (15) |
C3B—C4B | 1.539 (10) | C52—C53 | 1.410 (13) |
C5—C6 | 1.36 (2) | C53—C54 | 1.402 (14) |
C5—C10 | 1.407 (15) | C54—C55 | 1.375 (15) |
C6—C7 | 1.366 (15) | C54—C58 | 1.505 (14) |
C7—C8 | 1.354 (14) | C55—C56 | 1.36 (2) |
C8—C9 | 1.377 (14) | C56—C57 | 1.36 (2) |
C9—C10 | 1.354 (14) | | |
| | | |
C31—O1—C1B | 126.6 (15) | O10B—C26—C25 | 121.0 (11) |
C31—O1—C1A | 105.9 (12) | O10A—C26—C25 | 111.8 (8) |
C2A—O2A—C3A | 111.1 (9) | O10A—C27—C28A | 118.3 (12) |
C2B—O2B—C3B | 115.1 (11) | O10B—C27—C28B | 100.4 (9) |
C5—O3—C4A | 119.9 (11) | O11A—C28A—C27 | 108.8 (8) |
C5—O3—C4B | 115.0 (11) | O11B—C28B—C27 | 107.4 (7) |
C14—O4—C17 | 114.0 (7) | O11B—C29—C30 | 112.8 (9) |
C18—O5—C19 | 111.6 (8) | O11A—C29—C30 | 112.1 (8) |
C46—O6—C20 | 114.1 (9) | O12—C30—C29 | 117.9 (8) |
C53—O7—C21 | 113.8 (8) | C32—C31—O1 | 119.5 (9) |
C22—O8—C23A | 118.0 (10) | C32—C31—C36 | 122.4 (10) |
C22—O8—C23B | 115.4 (14) | O1—C31—C36 | 117.9 (9) |
C25—O9A—C24A | 114.7 (11) | C31—C32—C33 | 117.3 (10) |
C25—O9B—C24B | 111.1 (12) | C31—C32—C58 | 121.6 (9) |
C27—O10A—C26 | 113.0 (12) | C33—C32—C58 | 120.7 (10) |
C26—O10B—C27 | 112.0 (12) | C32—C33—C34 | 119.7 (11) |
C29—O11A—C28A | 118.3 (12) | C35—C34—C33 | 120.9 (12) |
C29—O11B—C28B | 118.7 (11) | C34—C35—C36 | 122.1 (13) |
C39—O12—C30 | 114.3 (7) | C35—C36—C31 | 116.9 (11) |
N2—N1—C8 | 115.1 (8) | C35—C36—C37 | 123.1 (11) |
N1—N2—C11 | 114.7 (7) | C31—C36—C37 | 119.4 (11) |
O1—C1A—C2A | 109.2 (10) | C36—C37—C38 | 112.8 (8) |
O1—C1B—C2B | 106.9 (10) | C39—C38—C43 | 118.6 (11) |
O2A—C2A—C1A | 109.5 (10) | C39—C38—C37 | 119.7 (10) |
O2B—C2B—C1B | 106.6 (10) | C43—C38—C37 | 121.5 (12) |
O2A—C3A—C4A | 105.9 (9) | C38—C39—C40 | 120.5 (11) |
O2B—C3B—C4B | 108.0 (10) | C38—C39—O12 | 120.1 (10) |
O3—C4A—C3A | 108.4 (10) | C40—C39—O12 | 119.3 (11) |
O3—C4B—C3B | 108.8 (11) | C39—C40—C41 | 118.3 (12) |
O3—C5—C6 | 129.1 (10) | C39—C40—C44 | 120.5 (11) |
O3—C5—C10 | 114.7 (11) | C41—C40—C44 | 120.7 (11) |
C6—C5—C10 | 116.2 (9) | C42—C41—C40 | 119.9 (12) |
C5—C6—C7 | 122.8 (11) | C43—C42—C41 | 121.8 (14) |
C8—C7—C6 | 120.7 (11) | C42—C43—C38 | 120.8 (13) |
C7—C8—C9 | 117.9 (9) | C40—C44—C45 | 110.0 (9) |
C7—C8—N1 | 118.2 (9) | C50—C45—C46 | 116.6 (10) |
C9—C8—N1 | 123.7 (9) | C50—C45—C44 | 121.2 (10) |
C10—C9—C8 | 121.9 (10) | C46—C45—C44 | 121.6 (10) |
C9—C10—C5 | 120.4 (11) | O6—C46—C47 | 118.8 (10) |
C12—C11—C16 | 120.5 (8) | O6—C46—C45 | 118.8 (9) |
C12—C11—N2 | 125.1 (9) | C47—C46—C45 | 122.2 (9) |
C16—C11—N2 | 114.4 (8) | C48—C47—C46 | 118.6 (11) |
C11—C12—C13 | 118.7 (9) | C48—C47—C51 | 121.4 (10) |
C14—C13—C12 | 121.9 (9) | C46—C47—C51 | 119.8 (9) |
C13—C14—O4 | 121.9 (9) | C47—C48—C49 | 121.9 (11) |
C13—C14—C15 | 118.8 (9) | C48—C49—C50 | 119.7 (12) |
O4—C14—C15 | 119.2 (10) | C45—C50—C49 | 120.7 (12) |
C16—C15—C14 | 120.7 (10) | C52—C51—C47 | 113.6 (8) |
C15—C16—C11 | 119.3 (9) | C57—C52—C53 | 117.5 (11) |
O4—C17—C18 | 111.5 (10) | C57—C52—C51 | 123.3 (10) |
O5—C18—C17 | 107.0 (9) | C53—C52—C51 | 118.7 (10) |
O5—C19—C20 | 109.7 (10) | C54—C53—C52 | 122.8 (10) |
O6—C20—C19 | 111.9 (8) | C54—C53—O7 | 118.8 (9) |
O7—C21—C22 | 109.6 (10) | C52—C53—O7 | 118.4 (9) |
O8—C22—C21 | 110.4 (12) | C55—C54—C53 | 115.6 (10) |
O8—C23A—C24A | 108.4 (10) | C55—C54—C58 | 121.2 (11) |
O8—C23B—C24B | 106.4 (11) | C53—C54—C58 | 122.7 (10) |
O9A—C24A—C23A | 108.7 (10) | C56—C55—C54 | 122.3 (12) |
O9B—C24B—C23B | 105.4 (11) | C55—C56—C57 | 121.1 (12) |
O9A—C25—C26 | 120.6 (10) | C52—C57—C56 | 120.4 (12) |
O9B—C25—C26 | 111.5 (9) | C54—C58—C32 | 108.4 (8) |
Crystal data top
C58H64N2O12 | Z = 4 |
Mr = 981.11 | F(000) = 2088 |
Triclinic, P1 | Dx = 1.253 Mg m−3 |
a = 20.285 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.608 (4) Å | Cell parameters from 25 reflections |
c = 23.894 (6) Å | θ = 8–12° |
α = 92.22 (3)° | µ = 0.09 mm−1 |
β = 112.32 (2)° | T = 213 K |
γ = 87.81 (3)° | Parallelepipedic, orange |
V = 5199 (3) Å3 | 0.65 × 0.60 × 0.50 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 23°, θmin = 1° |
Graphite monochromator | h = −22→22 |
w/2θ scans | k = 0→12 |
13177 measured reflections | l = −26→26 |
12513 independent reflections | 3 standard reflections every 60 min |
8852 reflections with I > 2σ(I) | intensity decay: 5.6% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.1351P)2 + 11.9644P], where P = (Fo2 + 2Fc2)/3 |
12460 reflections | (Δ/σ)max = 0.019 |
1290 parameters | Δρmax = 0.66 e Å−3 |
104 restraints | Δρmin = −0.50 e Å−3 |
Crystal data top
C58H64N2O12 | γ = 87.81 (3)° |
Mr = 981.11 | V = 5199 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 20.285 (8) Å | Mo Kα radiation |
b = 11.608 (4) Å | µ = 0.09 mm−1 |
c = 23.894 (6) Å | T = 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 reflections | θmax = 23° |
12513 independent reflections | 3 standard reflections every 60 min |
8852 reflections with I > 2σ(I) | intensity decay: 5.6% |
Refinement top
R[F2 > 2σ(F2)] = 0.080 | 104 restraints |
wR(F2) = 0.245 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.66 e Å−3 |
12460 reflections | Δρmin = −0.50 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.6766 (2) | 0.2402 (3) | 0.3401 (2) | 0.0503 (10) | |
O2A | 0.5797 (2) | 0.1675 (4) | 0.3966 (2) | 0.0634 (11) | |
O3A | 0.5821 (2) | 0.0195 (4) | 0.4933 (2) | 0.0592 (11) | |
O4A | 1.0698 (2) | −0.1506 (4) | 0.3628 (2) | 0.0601 (11) | |
O5A | 0.9616 (2) | −0.1535 (4) | 0.2332 (2) | 0.0616 (11) | |
O6A | 0.8209 (2) | −0.0406 (3) | 0.1889 (2) | 0.0483 (9) | |
O7A | 0.5699 (2) | 0.0950 (4) | 0.1301 (2) | 0.0717 (14) | |
O8I | 0.5033 (5) | 0.1802 (8) | 0.0016 (4) | 0.063 (3)* | 0.470 (7) |
O8J | 0.4803 (4) | 0.1603 (5) | 0.0172 (3) | 0.045 (2)* | 0.545 (7) |
O9I | 0.5764 (4) | 0.3189 (7) | −0.0551 (5) | 0.080 (3)* | 0.470 (7) |
O9J | 0.5495 (4) | 0.3515 (7) | −0.0243 (4) | 0.082 (3)* | 0.545 (7) |
O10A | 0.6621 (3) | 0.5072 (4) | 0.0271 (2) | 0.0681 (12) | |
O11A | 0.8265 (3) | 0.5504 (4) | 0.1511 (2) | 0.0794 (14) | |
O12A | 0.8221 (2) | 0.3878 (3) | 0.2396 (2) | 0.0414 (8) | |
N1A | 0.8382 (2) | −0.0867 (4) | 0.4668 (2) | 0.0415 (10) | |
N2A | 0.8388 (2) | −0.1685 (4) | 0.4311 (2) | 0.0444 (11) | |
C1A | 0.6654 (3) | 0.2951 (6) | 0.3908 (3) | 0.063 (2) | |
H1A1 | 0.6752 (3) | 0.3764 (6) | 0.3918 (3) | 0.076* | |
H1A2 | 0.6992 (3) | 0.2623 (6) | 0.4277 (3) | 0.076* | |
C2A | 0.5920 (3) | 0.2831 (6) | 0.3896 (3) | 0.064 (2) | |
H2A1 | 0.5863 (3) | 0.3302 (6) | 0.4219 (3) | 0.077* | |
H2A2 | 0.5574 (3) | 0.3101 (6) | 0.3514 (3) | 0.077* | |
C3A | 0.5194 (3) | 0.1556 (6) | 0.4126 (3) | 0.075 (2) | |
C4I | 0.5534 (12) | 0.1306 (15) | 0.4792 (6) | 0.064 (18)* | 0.14 (2) |
C4J | 0.5230 (3) | 0.0375 (6) | 0.4363 (3) | 0.068 (3)* | 0.87 (2) |
C5A | 0.6450 (2) | −0.0113 (5) | 0.4878 (2) | 0.0452 (14) | |
C6A | 0.6514 (3) | −0.1115 (5) | 0.4575 (3) | 0.0509 (14) | |
H6A | 0.6129 (3) | −0.1602 (5) | 0.4418 (3) | 0.061* | |
C7A | 0.7140 (3) | −0.1409 (5) | 0.4500 (2) | 0.0472 (14) | |
H7A | 0.7173 (3) | −0.2079 (5) | 0.4285 (2) | 0.057* | |
C8A | 0.7721 (3) | −0.0696 (5) | 0.4749 (2) | 0.0413 (13) | |
C9A | 0.7669 (3) | 0.0274 (5) | 0.5084 (2) | 0.0476 (14) | |
H9A | 0.8066 (3) | 0.0729 (5) | 0.5269 (2) | 0.057* | |
C10A | 0.7032 (3) | 0.0580 (5) | 0.5151 (2) | 0.0467 (13) | |
H10A | 0.6999 (3) | 0.1238 (5) | 0.5374 (2) | 0.056* | |
C11A | 0.9023 (3) | −0.1764 (4) | 0.4190 (2) | 0.0411 (12) | |
C12A | 0.9654 (3) | −0.1236 (5) | 0.4548 (2) | 0.0441 (13) | |
H12A | 0.9699 (3) | −0.0901 (5) | 0.4920 (2) | 0.053* | |
C13A | 1.0208 (3) | −0.1207 (5) | 0.4357 (2) | 0.0458 (13) | |
H13A | 1.0631 (3) | −0.0861 (5) | 0.4601 (2) | 0.055* | |
C14A | 1.0139 (3) | −0.1691 (5) | 0.3801 (3) | 0.0463 (13) | |
C15A | 0.9539 (3) | −0.2299 (5) | 0.3461 (3) | 0.0527 (15) | |
H15A | 0.9505 (3) | −0.2676 (5) | 0.3101 (3) | 0.063* | |
C16A | 0.8986 (3) | −0.2333 (5) | 0.3669 (3) | 0.0506 (14) | |
H16A | 0.8584 (3) | −0.2752 (5) | 0.3449 (3) | 0.061* | |
C17A | 1.0741 (3) | −0.2062 (6) | 0.3105 (3) | 0.063 (2) | |
H17A | 1.0538 (3) | −0.2819 (6) | 0.3061 (3) | 0.075* | |
H17B | 1.1240 (3) | −0.2173 (6) | 0.3168 (3) | 0.075* | |
C18A | 1.0373 (3) | −0.1438 (7) | 0.2526 (3) | 0.066 (2) | |
H18A | 1.0497 (3) | −0.0631 (7) | 0.2587 (3) | 0.080* | |
H18B | 1.0530 (3) | −0.1766 (7) | 0.2216 (3) | 0.080* | |
C19A | 0.9247 (3) | −0.1252 (6) | 0.1723 (3) | 0.058 (2) | |
H19A | 0.9381 (3) | −0.1791 (6) | 0.1462 (3) | 0.070* | |
H19B | 0.9367 (3) | −0.0482 (6) | 0.1656 (3) | 0.070* | |
C20A | 0.8461 (3) | −0.1305 (5) | 0.1580 (3) | 0.060 (2) | |
H20A | 0.8206 (3) | −0.1240 (5) | 0.1147 (3) | 0.072* | |
H20B | 0.8358 (3) | −0.2049 (5) | 0.1695 (3) | 0.072* | |
C21I | 0.5014 (5) | 0.0763 (11) | 0.0858 (4) | 0.062 (3)* | 0.470 (7) |
C21J | 0.5061 (4) | 0.0238 (7) | 0.0960 (4) | 0.047 (3)* | 0.545 (7) |
C22I | 0.4668 (6) | 0.1726 (10) | 0.0423 (5) | 0.058 (3)* | 0.470 (7) |
C22J | 0.4522 (5) | 0.1141 (8) | 0.0576 (4) | 0.048 (3)* | 0.545 (7) |
C23I | 0.4706 (6) | 0.2707 (11) | −0.0408 (5) | 0.072 (3)* | 0.470 (7) |
C23J | 0.4551 (6) | 0.2749 (8) | 0.0013 (5) | 0.074 (3)* | 0.545 (7) |
C24I | 0.5098 (6) | 0.2642 (10) | −0.0844 (5) | 0.082 (4)* | 0.470 (7) |
C24J | 0.4787 (5) | 0.3148 (11) | −0.0480 (5) | 0.088 (4)* | 0.545 (7) |
C25A | 0.5655 (4) | 0.4391 (6) | −0.0593 (3) | 0.092 (2) | |
C26A | 0.6416 (4) | 0.4808 (8) | −0.0344 (3) | 0.116 (3) | |
C27A | 0.7352 (4) | 0.5299 (7) | 0.0559 (3) | 0.077 (2) | |
H27A | 0.7462 (4) | 0.6001 (7) | 0.0408 (3) | 0.093* | |
H27B | 0.7636 (4) | 0.4668 (7) | 0.0482 (3) | 0.093* | |
C28A | 0.7510 (4) | 0.5431 (6) | 0.1228 (3) | 0.068 (2) | |
H28A | 0.7278 (4) | 0.6124 (6) | 0.1314 (3) | 0.082* | |
H28B | 0.7344 (4) | 0.4771 (6) | 0.1370 (3) | 0.082* | |
C29A | 0.8516 (4) | 0.5703 (6) | 0.2130 (3) | 0.077 (2) | |
H29A | 0.8136 (4) | 0.6074 (6) | 0.2229 (3) | 0.092* | |
H29B | 0.8902 (4) | 0.6242 (6) | 0.2239 (3) | 0.092* | |
C30A | 0.8780 (3) | 0.4664 (5) | 0.2513 (3) | 0.0530 (15) | |
H30A | 0.9167 (3) | 0.4288 (5) | 0.2426 (3) | 0.064* | |
H30B | 0.8962 (3) | 0.4900 (5) | 0.2937 (3) | 0.064* | |
C31A | 0.6553 (3) | 0.3081 (5) | 0.2894 (2) | 0.0439 (13) | |
C32A | 0.5947 (3) | 0.2740 (6) | 0.2402 (3) | 0.052 (2) | |
C33A | 0.5713 (3) | 0.3426 (7) | 0.1899 (3) | 0.065 (2) | |
H33A | 0.5299 (3) | 0.3239 (7) | 0.1573 (3) | 0.077* | |
C34A | 0.6081 (4) | 0.4375 (8) | 0.1874 (3) | 0.077 (2) | |
H34A | 0.5913 (4) | 0.4833 (8) | 0.1535 (3) | 0.092* | |
C35A | 0.6709 (3) | 0.4654 (6) | 0.2360 (3) | 0.059 (2) | |
H35A | 0.6958 (3) | 0.5297 (6) | 0.2339 (3) | 0.071* | |
C36A | 0.6968 (3) | 0.3984 (5) | 0.2874 (2) | 0.0431 (13) | |
C37A | 0.7708 (3) | 0.4145 (5) | 0.3341 (3) | 0.0511 (14) | |
H37A | 0.7692 (3) | 0.4197 (5) | 0.3742 (3) | 0.061* | |
H37B | 0.7897 (3) | 0.4857 (5) | 0.3271 (3) | 0.061* | |
C38A | 0.8185 (3) | 0.3139 (4) | 0.3303 (2) | 0.0421 (13) | |
C39A | 0.8389 (2) | 0.2987 (4) | 0.2814 (2) | 0.0397 (13) | |
C40A | 0.8729 (3) | 0.1987 (4) | 0.2706 (2) | 0.0419 (13) | |
C41A | 0.8887 (3) | 0.1128 (5) | 0.3140 (3) | 0.055 (2) | |
H41A | 0.9110 (3) | 0.0442 (5) | 0.3084 (3) | 0.066* | |
C42A | 0.8722 (3) | 0.1275 (5) | 0.3640 (3) | 0.057 (2) | |
H42A | 0.8846 (3) | 0.0702 (5) | 0.3926 (3) | 0.069* | |
C43A | 0.8371 (3) | 0.2271 (5) | 0.3726 (3) | 0.053 (2) | |
H43A | 0.8258 (3) | 0.2361 (5) | 0.4068 (3) | 0.064* | |
C44A | 0.8863 (3) | 0.1778 (5) | 0.2132 (3) | 0.0531 (15) | |
H44A | 0.9080 (3) | 0.2451 (5) | 0.2053 (3) | 0.064* | |
H44B | 0.9193 (3) | 0.1127 (5) | 0.2182 (3) | 0.064* | |
C45A | 0.8183 (3) | 0.1539 (5) | 0.1602 (2) | 0.0448 (13) | |
C46A | 0.7845 (3) | 0.0491 (4) | 0.1525 (2) | 0.0402 (12) | |
C47A | 0.7144 (3) | 0.0346 (5) | 0.1127 (2) | 0.0463 (14) | |
C48A | 0.6805 (3) | 0.1242 (6) | 0.0750 (3) | 0.064 (2) | |
H48A | 0.6341 (3) | 0.1157 (6) | 0.0471 (3) | 0.077* | |
C49A | 0.7149 (4) | 0.2263 (6) | 0.0783 (3) | 0.077 (2) | |
H49A | 0.6925 (4) | 0.2850 (6) | 0.0517 (3) | 0.093* | |
C50A | 0.7825 (4) | 0.2407 (5) | 0.1212 (3) | 0.063 (2) | |
H50A | 0.8047 (4) | 0.3105 (5) | 0.1240 (3) | 0.076* | |
C51A | 0.6729 (3) | −0.0684 (6) | 0.1174 (3) | 0.056 (2) | |
H51A | 0.6284 (3) | −0.0726 (6) | 0.0824 (3) | 0.067* | |
H51B | 0.7003 (3) | −0.1390 (6) | 0.1182 (3) | 0.067* | |
C52A | 0.6576 (3) | −0.0558 (5) | 0.1745 (3) | 0.0507 (15) | |
C53A | 0.6092 (3) | 0.0302 (6) | 0.1793 (3) | 0.059 (2) | |
C54A | 0.6039 (3) | 0.0579 (5) | 0.2348 (3) | 0.053 (2) | |
C55A | 0.6454 (3) | −0.0047 (6) | 0.2850 (3) | 0.061 (2) | |
H55A | 0.6424 (3) | 0.0127 (6) | 0.3223 (3) | 0.073* | |
C56A | 0.6908 (4) | −0.0919 (6) | 0.2802 (3) | 0.066 (2) | |
H56A | 0.7174 (4) | −0.1344 (6) | 0.3139 (3) | 0.080* | |
C57A | 0.6968 (3) | −0.1166 (5) | 0.2255 (3) | 0.061 (2) | |
H57A | 0.7280 (3) | −0.1755 (5) | 0.2229 (3) | 0.073* | |
C58A | 0.5589 (3) | 0.1625 (6) | 0.2402 (3) | 0.065 (2) | |
H58A | 0.5131 (3) | 0.1610 (6) | 0.2066 (3) | 0.077* | |
H58B | 0.5504 (3) | 0.1587 (6) | 0.2773 (3) | 0.077* | |
O1B | 0.3159 (2) | 0.5231 (3) | 0.2158 (2) | 0.0522 (10) | |
O2B | 0.4575 (2) | 0.7065 (5) | 0.2229 (2) | 0.0871 (15) | |
O3B | 0.5613 (2) | 0.6766 (5) | 0.3572 (2) | 0.0802 (15) | |
O4B | 0.0812 (2) | 0.4729 (4) | 0.4887 (2) | 0.0548 (10) | |
O5B | 0.0785 (2) | 0.3072 (3) | 0.3942 (2) | 0.0515 (10) | |
O6B | 0.1689 (2) | 0.2266 (3) | 0.32982 (15) | 0.0445 (9) | |
O7B | 0.0659 (2) | 0.4091 (3) | 0.13245 (15) | 0.0457 (9) | |
O8B | −0.0315 (3) | 0.3477 (4) | 0.0086 (2) | 0.0850 (15) | |
O9K | 0.0895 (5) | 0.1532 (8) | −0.0307 (4) | 0.102 (4)* | 0.623 (14) |
O9L | 0.0244 (7) | 0.0799 (10) | −0.0365 (7) | 0.135 (7)* | 0.383 (14) |
O10K | 0.2103 (7) | −0.0292 (15) | 0.0382 (9) | 0.145 (6)* | 0.354 (9) |
O10L | 0.1649 (5) | −0.1046 (8) | 0.0415 (5) | 0.139 (4)* | 0.682 (9) |
O11K | 0.3437 (8) | −0.0157 (12) | 0.1284 (7) | 0.098 (6)* | 0.354 (9) |
O11L | 0.2975 (4) | −0.0924 (7) | 0.1378 (4) | 0.097 (3)* | 0.682 (9) |
O12B | 0.3180 (2) | 0.1005 (3) | 0.2216 (2) | 0.0607 (11) | |
N1B | 0.3298 (2) | 0.6594 (4) | 0.4281 (2) | 0.0482 (11) | |
N2B | 0.3320 (2) | 0.5761 (4) | 0.4608 (2) | 0.0446 (11) | |
C1B | 0.3472 (3) | 0.6223 (6) | 0.2035 (3) | 0.068 (2) | |
H1B1 | 0.3359 (3) | 0.6898 (6) | 0.2237 (3) | 0.082* | |
H1B2 | 0.3279 (3) | 0.6353 (6) | 0.1603 (3) | 0.082* | |
C2B | 0.4284 (3) | 0.6039 (6) | 0.2259 (4) | 0.086 (3) | |
H2B1 | 0.4469 (3) | 0.5778 (6) | 0.2672 (4) | 0.103* | |
H2B2 | 0.4403 (3) | 0.5458 (6) | 0.2007 (4) | 0.103* | |
C3B | 0.5336 (4) | 0.7049 (8) | 0.2483 (3) | 0.089 (2) | |
H3B1 | 0.5505 (4) | 0.7501 (8) | 0.2233 (3) | 0.107* | |
H3B2 | 0.5510 (4) | 0.6261 (8) | 0.2472 (3) | 0.107* | |
C4B | 0.5646 (4) | 0.7513 (8) | 0.3123 (3) | 0.093 (3) | |
H4B1 | 0.6141 (4) | 0.7688 (8) | 0.3218 (3) | 0.111* | |
H4B2 | 0.5397 (4) | 0.8232 (8) | 0.3148 (3) | 0.111* | |
C5B | 0.5039 (3) | 0.6824 (6) | 0.3757 (3) | 0.060 (2) | |
C6B | 0.5079 (3) | 0.6054 (6) | 0.4192 (3) | 0.066 (2) | |
H6B | 0.5485 (3) | 0.5587 (6) | 0.4360 (3) | 0.079* | |
C7B | 0.4522 (3) | 0.5972 (6) | 0.4378 (3) | 0.063 (2) | |
H7B | 0.4548 (3) | 0.5431 (6) | 0.4664 (3) | 0.076* | |
C8B | 0.3924 (3) | 0.6680 (5) | 0.4149 (2) | 0.0456 (13) | |
C9B | 0.3903 (3) | 0.7486 (5) | 0.3739 (3) | 0.061 (2) | |
H9B | 0.3513 (3) | 0.7995 (5) | 0.3596 (3) | 0.074* | |
C10B | 0.4455 (4) | 0.7553 (6) | 0.3534 (3) | 0.068 (2) | |
H10B | 0.4429 (4) | 0.8090 (6) | 0.3246 (3) | 0.082* | |
C11B | 0.2677 (3) | 0.5613 (5) | 0.4704 (2) | 0.0410 (12) | |
C12B | 0.2085 (3) | 0.6361 (5) | 0.4512 (2) | 0.0446 (13) | |
H12B | 0.2108 (3) | 0.7055 (5) | 0.4339 (2) | 0.053* | |
C13B | 0.1473 (3) | 0.6083 (5) | 0.4574 (2) | 0.0482 (14) | |
H13B | 0.1080 (3) | 0.6586 (5) | 0.4445 (2) | 0.058* | |
C14B | 0.1434 (3) | 0.5044 (5) | 0.4833 (2) | 0.0457 (14) | |
C15B | 0.2022 (3) | 0.4324 (5) | 0.5051 (3) | 0.0492 (14) | |
H15B | 0.2004 (3) | 0.3648 (5) | 0.5240 (3) | 0.059* | |
C16B | 0.2642 (3) | 0.4615 (5) | 0.4986 (2) | 0.0484 (14) | |
H16B | 0.3043 (3) | 0.4131 (5) | 0.5136 (2) | 0.058* | |
C17B | 0.0220 (3) | 0.4531 (6) | 0.4330 (3) | 0.057 (2) | |
H17C | 0.0253 (3) | 0.5024 (6) | 0.4023 (3) | 0.069* | |
H17D | −0.0220 (3) | 0.4733 (6) | 0.4385 (3) | 0.069* | |
C18B | 0.0203 (3) | 0.3309 (5) | 0.4120 (3) | 0.0516 (15) | |
H18C | 0.0232 (3) | 0.2806 (5) | 0.4444 (3) | 0.062* | |
H18D | −0.0241 (3) | 0.3168 (5) | 0.3781 (3) | 0.062* | |
C19B | 0.0863 (3) | 0.1900 (5) | 0.3793 (3) | 0.0531 (15) | |
H19C | 0.0497 (3) | 0.1706 (5) | 0.3404 (3) | 0.064* | |
H19D | 0.0806 (3) | 0.1419 (5) | 0.4094 (3) | 0.064* | |
C20B | 0.1579 (3) | 0.1672 (6) | 0.3770 (2) | 0.055 (2) | |
H20C | 0.1940 (3) | 0.1900 (6) | 0.4156 (2) | 0.066* | |
H20D | 0.1641 (3) | 0.0849 (6) | 0.3711 (2) | 0.066* | |
C21B | 0.0012 (3) | 0.4697 (5) | 0.0984 (3) | 0.058 (2) | |
H21A | 0.0112 (3) | 0.5298 (5) | 0.0758 (3) | 0.070* | |
H21B | −0.0190 (3) | 0.5059 (5) | 0.1257 (3) | 0.070* | |
C22B | −0.0510 (3) | 0.3888 (6) | 0.0556 (3) | 0.072 (2) | |
H22A | −0.0559 (3) | 0.3239 (6) | 0.0780 (3) | 0.087* | |
H22B | −0.0971 (3) | 0.4281 (6) | 0.0388 (3) | 0.087* | |
C23B | 0.0162 (5) | 0.2488 (7) | 0.0200 (4) | 0.109 (3) | |
C24K | 0.0258 (8) | 0.2204 (11) | −0.0414 (6) | 0.108 (5)* | 0.623 (14) |
C24L | −0.0042 (11) | 0.1897 (15) | −0.0444 (7) | 0.117 (7)* | 0.383 (14) |
C25B | 0.0952 (5) | 0.0583 (9) | 0.0012 (6) | 0.161 (5) | |
C26K | 0.1437 (10) | −0.039 (2) | −0.0102 (10) | 0.139 (6)* | 0.354 (9) |
C26L | 0.1600 (8) | −0.0130 (12) | 0.0004 (8) | 0.139 (5)* | 0.682 (9) |
C27K | 0.2527 (8) | −0.1302 (13) | 0.0558 (9) | 0.090 (7)* | 0.354 (9) |
C27L | 0.2199 (6) | −0.1856 (10) | 0.0471 (6) | 0.120 (7)* | 0.682 (9) |
C28K | 0.3309 (7) | −0.0923 (19) | 0.0766 (7) | 0.123 (10)* | 0.354 (9) |
C28L | 0.2914 (6) | −0.1324 (13) | 0.0788 (5) | 0.123 (5)* | 0.682 (9) |
C29K | 0.3422 (14) | −0.0764 (14) | 0.1778 (6) | 0.087 (7)* | 0.354 (9) |
C29L | 0.3653 (5) | −0.0442 (12) | 0.1702 (4) | 0.086 (4)* | 0.682 (9) |
C30B | 0.3714 (4) | 0.0085 (6) | 0.2314 (3) | 0.089 (3) | |
C31B | 0.2846 (3) | 0.4494 (5) | 0.1667 (2) | 0.0431 (13) | |
C32B | 0.2168 (3) | 0.4768 (5) | 0.1241 (2) | 0.0436 (13) | |
C33B | 0.1889 (3) | 0.4035 (6) | 0.0741 (3) | 0.056 (2) | |
H33B | 0.1446 (3) | 0.4208 (6) | 0.0443 (3) | 0.067* | |
C34B | 0.2259 (4) | 0.3057 (6) | 0.0679 (3) | 0.069 (2) | |
H34B | 0.2081 (4) | 0.2603 (6) | 0.0327 (3) | 0.082* | |
C35B | 0.2888 (4) | 0.2743 (5) | 0.1131 (3) | 0.063 (2) | |
H35B | 0.3113 (4) | 0.2048 (5) | 0.1094 (3) | 0.076* | |
C36B | 0.3194 (3) | 0.3442 (5) | 0.1641 (3) | 0.0480 (14) | |
C37B | 0.3849 (3) | 0.3058 (6) | 0.2171 (3) | 0.062 (2) | |
H37C | 0.4195 (3) | 0.3665 (6) | 0.2286 (3) | 0.074* | |
H37D | 0.4064 (3) | 0.2382 (6) | 0.2049 (3) | 0.074* | |
C38B | 0.3675 (3) | 0.2771 (5) | 0.2713 (3) | 0.054 (2) | |
C39B | 0.3335 (3) | 0.1758 (5) | 0.2713 (3) | 0.0521 (15) | |
C40B | 0.3116 (3) | 0.1508 (5) | 0.3182 (3) | 0.053 (2) | |
C41B | 0.3277 (3) | 0.2269 (6) | 0.3667 (3) | 0.058 (2) | |
H41B | 0.3147 (3) | 0.2103 (6) | 0.3988 (3) | 0.069* | |
C42B | 0.3627 (3) | 0.3271 (6) | 0.3688 (3) | 0.066 (2) | |
H42B | 0.3738 (3) | 0.3772 (6) | 0.4022 (3) | 0.079* | |
C43B | 0.3814 (3) | 0.3531 (6) | 0.3207 (3) | 0.063 (2) | |
H43B | 0.4035 (3) | 0.4222 (6) | 0.3215 (3) | 0.075* | |
C44B | 0.2626 (3) | 0.0500 (5) | 0.3123 (3) | 0.059 (2) | |
H44C | 0.2822 (3) | −0.0197 (5) | 0.3001 (3) | 0.071* | |
H44D | 0.2594 (3) | 0.0373 (5) | 0.3510 (3) | 0.071* | |
C45B | 0.1889 (3) | 0.0768 (5) | 0.2654 (3) | 0.0495 (14) | |
C46B | 0.1473 (3) | 0.1687 (5) | 0.2745 (2) | 0.0420 (13) | |
C47B | 0.0866 (3) | 0.2105 (5) | 0.2282 (2) | 0.0419 (13) | |
C48B | 0.0630 (3) | 0.1483 (6) | 0.1739 (3) | 0.057 (2) | |
H48B | 0.0212 (3) | 0.1714 (6) | 0.1427 (3) | 0.068* | |
C49B | 0.1009 (4) | 0.0525 (6) | 0.1657 (3) | 0.066 (2) | |
H49B | 0.0834 (4) | 0.0102 (6) | 0.1294 (3) | 0.079* | |
C50B | 0.1640 (4) | 0.0185 (5) | 0.2099 (3) | 0.059 (2) | |
H50B | 0.1901 (4) | −0.0439 (5) | 0.2027 (3) | 0.071* | |
C51B | 0.0513 (3) | 0.3230 (5) | 0.2358 (3) | 0.0516 (15) | |
H51C | 0.0416 (3) | 0.3218 (5) | 0.2726 (3) | 0.062* | |
H51D | 0.0061 (3) | 0.3320 (5) | 0.2020 (3) | 0.062* | |
C52B | 0.0973 (3) | 0.4248 (5) | 0.2392 (2) | 0.0418 (13) | |
C53B | 0.1058 (3) | 0.4625 (5) | 0.1879 (2) | 0.0413 (13) | |
C54B | 0.1538 (3) | 0.5475 (5) | 0.1906 (2) | 0.0461 (13) | |
C55B | 0.1903 (3) | 0.5997 (5) | 0.2466 (3) | 0.0533 (15) | |
H55B | 0.2209 (3) | 0.6594 (5) | 0.2495 (3) | 0.064* | |
C56B | 0.1820 (3) | 0.5650 (5) | 0.2976 (3) | 0.055 (2) | |
H56B | 0.2075 (3) | 0.6003 (5) | 0.3348 (3) | 0.066* | |
C57B | 0.1363 (3) | 0.4786 (5) | 0.2941 (3) | 0.0522 (15) | |
H57B | 0.1315 (3) | 0.4556 (5) | 0.3292 (3) | 0.063* | |
C58B | 0.1717 (3) | 0.5751 (5) | 0.1362 (3) | 0.0522 (15) | |
H58C | 0.1281 (3) | 0.5854 (5) | 0.1009 (3) | 0.063* | |
H58D | 0.1977 (3) | 0.6462 (5) | 0.1442 (3) | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.046 (2) | 0.066 (3) | 0.037 (2) | −0.009 (2) | 0.013 (2) | −0.001 (2) |
O2A | 0.047 (2) | 0.088 (3) | 0.064 (3) | 0.005 (2) | 0.029 (2) | 0.021 (2) |
O3A | 0.035 (2) | 0.102 (3) | 0.046 (2) | 0.001 (2) | 0.020 (2) | 0.011 (2) |
O4A | 0.043 (2) | 0.085 (3) | 0.055 (2) | 0.003 (2) | 0.024 (2) | −0.001 (2) |
O5A | 0.041 (2) | 0.086 (3) | 0.058 (3) | 0.004 (2) | 0.018 (2) | 0.021 (2) |
O6A | 0.042 (2) | 0.043 (2) | 0.054 (2) | −0.001 (2) | 0.011 (2) | 0.006 (2) |
O7A | 0.031 (2) | 0.121 (4) | 0.044 (2) | 0.012 (2) | −0.005 (2) | −0.024 (2) |
O10A | 0.083 (3) | 0.067 (3) | 0.053 (3) | 0.008 (2) | 0.024 (2) | 0.011 (2) |
O11A | 0.088 (4) | 0.078 (3) | 0.071 (3) | −0.023 (3) | 0.025 (3) | 0.017 (3) |
O12A | 0.042 (2) | 0.032 (2) | 0.047 (2) | −0.007 (2) | 0.013 (2) | 0.006 (2) |
N1A | 0.038 (2) | 0.041 (3) | 0.046 (3) | 0.002 (2) | 0.017 (2) | 0.004 (2) |
N2A | 0.044 (3) | 0.043 (3) | 0.045 (3) | −0.002 (2) | 0.016 (2) | 0.004 (2) |
C1A | 0.070 (4) | 0.087 (5) | 0.034 (3) | −0.020 (4) | 0.020 (3) | −0.007 (3) |
C2A | 0.067 (4) | 0.089 (5) | 0.041 (3) | 0.004 (4) | 0.026 (3) | 0.001 (3) |
C3A | 0.040 (3) | 0.125 (6) | 0.070 (4) | 0.011 (4) | 0.032 (3) | 0.027 (4) |
C5A | 0.034 (3) | 0.065 (4) | 0.039 (3) | 0.002 (3) | 0.014 (2) | 0.015 (3) |
C6A | 0.035 (3) | 0.065 (4) | 0.052 (3) | −0.012 (3) | 0.016 (3) | 0.001 (3) |
C7A | 0.044 (3) | 0.052 (3) | 0.040 (3) | −0.008 (3) | 0.009 (3) | 0.000 (3) |
C8A | 0.034 (3) | 0.051 (3) | 0.038 (3) | 0.000 (2) | 0.012 (2) | 0.008 (3) |
C9A | 0.038 (3) | 0.054 (4) | 0.051 (3) | −0.006 (3) | 0.017 (3) | 0.001 (3) |
C10A | 0.044 (3) | 0.049 (3) | 0.050 (3) | 0.000 (3) | 0.022 (3) | 0.002 (3) |
C11A | 0.046 (3) | 0.033 (3) | 0.046 (3) | 0.001 (2) | 0.019 (3) | 0.005 (2) |
C12A | 0.040 (3) | 0.049 (3) | 0.041 (3) | 0.003 (3) | 0.013 (3) | −0.003 (2) |
C13A | 0.033 (3) | 0.047 (3) | 0.053 (3) | 0.006 (2) | 0.012 (3) | −0.002 (3) |
C14A | 0.042 (3) | 0.048 (3) | 0.052 (3) | 0.008 (3) | 0.022 (3) | 0.008 (3) |
C15A | 0.062 (4) | 0.056 (4) | 0.045 (3) | −0.003 (3) | 0.026 (3) | −0.002 (3) |
C16A | 0.052 (3) | 0.049 (3) | 0.049 (3) | −0.012 (3) | 0.017 (3) | −0.004 (3) |
C17A | 0.049 (4) | 0.082 (5) | 0.062 (4) | 0.014 (3) | 0.027 (3) | 0.006 (3) |
C18A | 0.048 (4) | 0.096 (5) | 0.061 (4) | 0.005 (3) | 0.028 (3) | 0.009 (4) |
C19A | 0.056 (4) | 0.060 (4) | 0.059 (4) | 0.009 (3) | 0.022 (3) | 0.006 (3) |
C20A | 0.057 (4) | 0.038 (3) | 0.078 (4) | 0.007 (3) | 0.017 (3) | −0.002 (3) |
C25A | 0.107 (6) | 0.095 (6) | 0.056 (4) | −0.002 (5) | 0.008 (4) | 0.018 (4) |
C26A | 0.099 (7) | 0.203 (11) | 0.044 (4) | 0.032 (7) | 0.025 (4) | 0.022 (5) |
C27A | 0.082 (5) | 0.081 (5) | 0.071 (5) | 0.000 (4) | 0.029 (4) | 0.026 (4) |
C28A | 0.080 (5) | 0.054 (4) | 0.067 (4) | −0.006 (3) | 0.021 (4) | 0.011 (3) |
C29A | 0.107 (6) | 0.051 (4) | 0.065 (5) | −0.038 (4) | 0.019 (4) | 0.006 (3) |
C30A | 0.059 (4) | 0.045 (3) | 0.054 (4) | −0.016 (3) | 0.018 (3) | 0.004 (3) |
C31A | 0.036 (3) | 0.063 (4) | 0.033 (3) | 0.008 (3) | 0.015 (2) | −0.001 (3) |
C32A | 0.033 (3) | 0.084 (4) | 0.042 (3) | 0.005 (3) | 0.017 (3) | −0.007 (3) |
C33A | 0.045 (4) | 0.097 (5) | 0.046 (4) | 0.013 (4) | 0.012 (3) | 0.002 (4) |
C34A | 0.058 (4) | 0.118 (7) | 0.048 (4) | 0.038 (4) | 0.014 (3) | 0.026 (4) |
C35A | 0.057 (4) | 0.063 (4) | 0.060 (4) | 0.020 (3) | 0.027 (3) | 0.014 (3) |
C36A | 0.044 (3) | 0.049 (3) | 0.041 (3) | 0.010 (3) | 0.021 (3) | 0.003 (3) |
C37A | 0.053 (3) | 0.056 (4) | 0.044 (3) | −0.007 (3) | 0.018 (3) | −0.001 (3) |
C38A | 0.034 (3) | 0.042 (3) | 0.045 (3) | −0.011 (2) | 0.007 (2) | 0.005 (2) |
C39A | 0.028 (3) | 0.041 (3) | 0.045 (3) | −0.012 (2) | 0.005 (2) | 0.010 (2) |
C40A | 0.028 (3) | 0.031 (3) | 0.059 (4) | −0.005 (2) | 0.008 (2) | 0.000 (3) |
C41A | 0.034 (3) | 0.041 (3) | 0.075 (4) | −0.002 (2) | 0.004 (3) | 0.007 (3) |
C42A | 0.044 (3) | 0.056 (4) | 0.061 (4) | −0.001 (3) | 0.005 (3) | 0.024 (3) |
C43A | 0.039 (3) | 0.063 (4) | 0.049 (3) | −0.012 (3) | 0.005 (3) | 0.013 (3) |
C44A | 0.048 (3) | 0.038 (3) | 0.081 (4) | −0.004 (3) | 0.034 (3) | −0.004 (3) |
C45A | 0.046 (3) | 0.043 (3) | 0.051 (3) | 0.001 (3) | 0.025 (3) | −0.001 (3) |
C46A | 0.041 (3) | 0.036 (3) | 0.045 (3) | 0.003 (2) | 0.017 (3) | 0.007 (2) |
C47A | 0.040 (3) | 0.057 (4) | 0.039 (3) | 0.007 (3) | 0.013 (3) | −0.007 (3) |
C48A | 0.064 (4) | 0.064 (4) | 0.046 (4) | 0.024 (4) | 0.004 (3) | −0.011 (3) |
C49A | 0.118 (6) | 0.047 (4) | 0.049 (4) | 0.031 (4) | 0.014 (4) | 0.008 (3) |
C50A | 0.088 (5) | 0.041 (3) | 0.055 (4) | 0.000 (3) | 0.022 (4) | 0.002 (3) |
C51A | 0.032 (3) | 0.077 (4) | 0.053 (4) | −0.011 (3) | 0.010 (3) | −0.020 (3) |
C52A | 0.035 (3) | 0.059 (4) | 0.059 (4) | −0.019 (3) | 0.019 (3) | −0.015 (3) |
C53A | 0.030 (3) | 0.086 (5) | 0.050 (4) | −0.019 (3) | 0.005 (3) | −0.019 (3) |
C54A | 0.034 (3) | 0.072 (4) | 0.054 (4) | −0.022 (3) | 0.018 (3) | −0.020 (3) |
C55A | 0.064 (4) | 0.072 (4) | 0.058 (4) | −0.029 (4) | 0.034 (4) | −0.003 (3) |
C56A | 0.085 (5) | 0.057 (4) | 0.071 (5) | −0.013 (4) | 0.044 (4) | 0.013 (3) |
C57A | 0.065 (4) | 0.051 (4) | 0.068 (4) | −0.020 (3) | 0.026 (4) | 0.003 (3) |
C58A | 0.032 (3) | 0.113 (6) | 0.048 (4) | −0.015 (3) | 0.017 (3) | −0.026 (4) |
O1B | 0.045 (2) | 0.056 (2) | 0.050 (2) | −0.015 (2) | 0.012 (2) | −0.002 (2) |
O2B | 0.062 (3) | 0.095 (4) | 0.099 (4) | −0.021 (3) | 0.023 (3) | −0.002 (3) |
O3B | 0.048 (3) | 0.116 (4) | 0.079 (3) | −0.027 (3) | 0.022 (2) | 0.030 (3) |
O4B | 0.040 (2) | 0.080 (3) | 0.048 (2) | −0.002 (2) | 0.022 (2) | −0.006 (2) |
O5B | 0.043 (2) | 0.069 (3) | 0.052 (2) | −0.008 (2) | 0.027 (2) | −0.005 (2) |
O6B | 0.041 (2) | 0.055 (2) | 0.036 (2) | 0.005 (2) | 0.013 (2) | 0.004 (2) |
O7B | 0.037 (2) | 0.054 (2) | 0.037 (2) | 0.004 (2) | 0.004 (2) | 0.004 (2) |
O8B | 0.104 (4) | 0.073 (3) | 0.062 (3) | −0.001 (3) | 0.013 (3) | 0.005 (3) |
O12B | 0.065 (3) | 0.046 (2) | 0.085 (3) | 0.017 (2) | 0.045 (2) | 0.012 (2) |
N1B | 0.045 (3) | 0.050 (3) | 0.044 (3) | −0.006 (2) | 0.010 (2) | 0.004 (2) |
N2B | 0.039 (3) | 0.047 (3) | 0.042 (3) | −0.008 (2) | 0.009 (2) | 0.005 (2) |
C1B | 0.056 (4) | 0.059 (4) | 0.083 (5) | −0.022 (3) | 0.018 (3) | 0.000 (3) |
C2B | 0.089 (5) | 0.052 (4) | 0.159 (8) | −0.027 (4) | 0.092 (6) | −0.006 (4) |
C3B | 0.057 (4) | 0.130 (7) | 0.076 (5) | −0.030 (4) | 0.018 (4) | −0.006 (5) |
C4B | 0.073 (5) | 0.132 (7) | 0.077 (5) | −0.045 (5) | 0.030 (4) | 0.000 (5) |
C5B | 0.046 (4) | 0.069 (4) | 0.063 (4) | −0.023 (3) | 0.018 (3) | 0.003 (3) |
C6B | 0.039 (3) | 0.077 (5) | 0.073 (4) | −0.009 (3) | 0.010 (3) | 0.020 (4) |
C7B | 0.042 (3) | 0.079 (5) | 0.062 (4) | −0.007 (3) | 0.010 (3) | 0.029 (3) |
C8B | 0.038 (3) | 0.046 (3) | 0.046 (3) | −0.009 (3) | 0.008 (3) | 0.004 (3) |
C9B | 0.062 (4) | 0.053 (4) | 0.070 (4) | 0.003 (3) | 0.024 (3) | 0.015 (3) |
C10B | 0.071 (5) | 0.060 (4) | 0.080 (5) | −0.010 (4) | 0.034 (4) | 0.021 (4) |
C11B | 0.038 (3) | 0.047 (3) | 0.033 (3) | −0.007 (2) | 0.007 (2) | −0.003 (2) |
C12B | 0.045 (3) | 0.043 (3) | 0.041 (3) | 0.002 (3) | 0.012 (3) | 0.003 (2) |
C13B | 0.050 (3) | 0.050 (3) | 0.049 (3) | 0.010 (3) | 0.024 (3) | 0.001 (3) |
C14B | 0.042 (3) | 0.063 (4) | 0.034 (3) | −0.001 (3) | 0.017 (2) | −0.008 (3) |
C15B | 0.046 (3) | 0.049 (3) | 0.052 (3) | −0.002 (3) | 0.018 (3) | 0.005 (3) |
C16B | 0.035 (3) | 0.055 (4) | 0.050 (3) | 0.000 (3) | 0.009 (3) | 0.009 (3) |
C17B | 0.037 (3) | 0.080 (5) | 0.055 (4) | 0.004 (3) | 0.018 (3) | 0.000 (3) |
C18B | 0.032 (3) | 0.079 (4) | 0.047 (3) | −0.002 (3) | 0.019 (3) | 0.003 (3) |
C19B | 0.051 (3) | 0.061 (4) | 0.048 (3) | −0.003 (3) | 0.019 (3) | 0.003 (3) |
C20B | 0.048 (3) | 0.077 (4) | 0.039 (3) | 0.010 (3) | 0.018 (3) | 0.012 (3) |
C21B | 0.047 (3) | 0.072 (4) | 0.044 (3) | 0.011 (3) | 0.005 (3) | 0.014 (3) |
C22B | 0.048 (4) | 0.093 (5) | 0.060 (4) | −0.001 (4) | 0.002 (3) | 0.020 (4) |
C23B | 0.153 (9) | 0.092 (6) | 0.072 (5) | −0.015 (6) | 0.032 (6) | −0.021 (5) |
C25B | 0.126 (10) | 0.148 (11) | 0.189 (13) | −0.006 (8) | 0.029 (9) | 0.066 (10) |
C30B | 0.103 (6) | 0.076 (5) | 0.111 (6) | 0.055 (4) | 0.068 (5) | 0.034 (4) |
C31B | 0.041 (3) | 0.050 (3) | 0.040 (3) | −0.010 (3) | 0.017 (3) | 0.009 (3) |
C32B | 0.041 (3) | 0.048 (3) | 0.044 (3) | −0.006 (3) | 0.017 (3) | 0.008 (3) |
C33B | 0.052 (4) | 0.067 (4) | 0.047 (4) | −0.014 (3) | 0.014 (3) | 0.002 (3) |
C34B | 0.077 (5) | 0.065 (4) | 0.065 (4) | −0.017 (4) | 0.028 (4) | −0.009 (3) |
C35B | 0.071 (4) | 0.048 (4) | 0.081 (5) | 0.000 (3) | 0.041 (4) | 0.005 (3) |
C36B | 0.047 (3) | 0.049 (3) | 0.058 (4) | −0.001 (3) | 0.030 (3) | 0.008 (3) |
C37B | 0.041 (3) | 0.069 (4) | 0.080 (4) | 0.006 (3) | 0.027 (3) | 0.024 (3) |
C38B | 0.031 (3) | 0.061 (4) | 0.068 (4) | 0.012 (3) | 0.016 (3) | 0.023 (3) |
C39B | 0.036 (3) | 0.061 (4) | 0.060 (4) | 0.017 (3) | 0.019 (3) | 0.015 (3) |
C40B | 0.036 (3) | 0.063 (4) | 0.065 (4) | 0.015 (3) | 0.023 (3) | 0.020 (3) |
C41B | 0.035 (3) | 0.082 (5) | 0.056 (4) | 0.011 (3) | 0.016 (3) | 0.019 (4) |
C42B | 0.045 (4) | 0.081 (5) | 0.060 (4) | 0.004 (3) | 0.008 (3) | 0.014 (4) |
C43B | 0.038 (3) | 0.067 (4) | 0.067 (4) | −0.001 (3) | 0.001 (3) | 0.016 (4) |
C44B | 0.056 (4) | 0.056 (4) | 0.078 (4) | 0.016 (3) | 0.037 (3) | 0.023 (3) |
C45B | 0.057 (4) | 0.050 (3) | 0.053 (4) | −0.004 (3) | 0.034 (3) | 0.009 (3) |
C46B | 0.037 (3) | 0.053 (3) | 0.039 (3) | −0.005 (3) | 0.018 (3) | 0.003 (3) |
C47B | 0.037 (3) | 0.051 (3) | 0.042 (3) | −0.012 (3) | 0.019 (3) | 0.003 (3) |
C48B | 0.056 (4) | 0.068 (4) | 0.046 (4) | −0.018 (3) | 0.017 (3) | 0.007 (3) |
C49B | 0.090 (5) | 0.058 (4) | 0.053 (4) | −0.027 (4) | 0.030 (4) | −0.005 (3) |
C50B | 0.080 (5) | 0.044 (3) | 0.070 (4) | −0.010 (3) | 0.047 (4) | 0.002 (3) |
C51B | 0.032 (3) | 0.077 (4) | 0.045 (3) | 0.006 (3) | 0.013 (3) | 0.018 (3) |
C52B | 0.033 (3) | 0.055 (3) | 0.037 (3) | 0.013 (2) | 0.013 (2) | 0.008 (3) |
C53B | 0.032 (3) | 0.048 (3) | 0.039 (3) | 0.007 (2) | 0.009 (2) | 0.000 (2) |
C54B | 0.045 (3) | 0.042 (3) | 0.046 (3) | 0.010 (3) | 0.012 (3) | 0.010 (3) |
C55B | 0.051 (3) | 0.048 (3) | 0.054 (4) | 0.000 (3) | 0.013 (3) | −0.003 (3) |
C56B | 0.052 (4) | 0.057 (4) | 0.049 (4) | 0.012 (3) | 0.011 (3) | −0.008 (3) |
C57B | 0.054 (4) | 0.057 (4) | 0.046 (3) | 0.013 (3) | 0.021 (3) | 0.000 (3) |
C58B | 0.048 (3) | 0.049 (3) | 0.054 (4) | −0.001 (3) | 0.011 (3) | 0.012 (3) |
Geometric parameters (Å, º) top
O1A—C31A | 1.389 (6) | O1B—C1B | 1.429 (7) |
O1A—C1A | 1.435 (7) | O2B—C2B | 1.366 (7) |
O2A—C2A | 1.403 (8) | O2B—C3B | 1.427 (8) |
O2A—C3A | 1.426 (7) | O3B—C5B | 1.391 (7) |
O3A—C5A | 1.365 (6) | O3B—C4B | 1.428 (8) |
O3A—C4I | 1.394 (10) | O4B—C14B | 1.381 (6) |
O3A—C4J | 1.448 (6) | O4B—C17B | 1.432 (7) |
O4A—C14A | 1.372 (6) | O5B—C19B | 1.412 (7) |
O4A—C17A | 1.414 (7) | O5B—C18B | 1.413 (6) |
O5A—C19A | 1.406 (7) | O6B—C46B | 1.379 (6) |
O5A—C18A | 1.433 (7) | O6B—C20B | 1.436 (6) |
O6A—C46A | 1.383 (6) | O7B—C53B | 1.397 (6) |
O6A—C20A | 1.442 (7) | O7B—C21B | 1.429 (6) |
O7A—C53A | 1.377 (8) | O8B—C22B | 1.389 (8) |
O7A—C21I | 1.408 (9) | O8B—C23B | 1.439 (9) |
O7A—C21J | 1.499 (8) | O9K—C25B | 1.340 (8) |
O8I—C22I | 1.436 (9) | O9K—C24K | 1.426 (8) |
O8I—C23I | 1.445 (9) | O9L—C24L | 1.369 (9) |
O8J—C23J | 1.419 (8) | O9L—C25B | 1.394 (9) |
O8J—C22J | 1.422 (8) | O10K—C27K | 1.406 (10) |
O9I—C25A | 1.406 (8) | O10K—C26K | 1.410 (10) |
O9I—C24I | 1.424 (9) | O10L—C27L | 1.401 (9) |
O9J—C24J | 1.406 (9) | O10L—C26L | 1.450 (10) |
O9J—C25A | 1.463 (7) | O11K—C29K | 1.409 (10) |
O10A—C26A | 1.390 (8) | O11K—C28K | 1.441 (10) |
O10A—C27A | 1.408 (8) | O11L—C29L | 1.422 (8) |
O11A—C29A | 1.382 (8) | O11L—C28L | 1.428 (9) |
O11A—C28A | 1.425 (8) | O12B—C39B | 1.391 (7) |
O12A—C39A | 1.406 (6) | O12B—C30B | 1.451 (7) |
O12A—C30A | 1.420 (6) | N1B—N2B | 1.255 (6) |
N1A—N2A | 1.255 (6) | N1B—C8B | 1.427 (7) |
N1A—C8A | 1.430 (6) | N2B—C11B | 1.426 (7) |
N2A—C11A | 1.423 (7) | C1B—C2B | 1.535 (7) |
C1A—C2A | 1.490 (8) | C3B—C4B | 1.503 (10) |
C3A—C4J | 1.493 (8) | C5B—C10B | 1.373 (9) |
C3A—C4I | 1.511 (11) | C5B—C6B | 1.375 (8) |
C5A—C6A | 1.375 (8) | C6B—C7B | 1.372 (8) |
C5A—C10A | 1.383 (7) | C7B—C8B | 1.378 (8) |
C6A—C7A | 1.376 (8) | C8B—C9B | 1.369 (8) |
C7A—C8A | 1.391 (7) | C9B—C10B | 1.388 (9) |
C8A—C9A | 1.381 (8) | C11B—C16B | 1.380 (7) |
C9A—C10A | 1.392 (7) | C11B—C12B | 1.393 (7) |
C11A—C16A | 1.364 (7) | C12B—C13B | 1.356 (7) |
C11A—C12A | 1.389 (7) | C13B—C14B | 1.394 (8) |
C12A—C13A | 1.367 (7) | C14B—C15B | 1.371 (8) |
C13A—C14A | 1.382 (8) | C15B—C16B | 1.379 (7) |
C14A—C15A | 1.382 (8) | C17B—C18B | 1.483 (8) |
C15A—C16A | 1.390 (8) | C19B—C20B | 1.487 (8) |
C17A—C18A | 1.500 (8) | C21B—C22B | 1.492 (9) |
C19A—C20A | 1.502 (8) | C23B—C24L | 1.57 (2) |
C21I—C22I | 1.515 (9) | C23B—C24K | 1.572 (13) |
C21J—C22J | 1.536 (8) | C25B—C26L | 1.533 (10) |
C23I—C24I | 1.531 (9) | C25B—C26K | 1.549 (10) |
C23J—C24J | 1.524 (9) | C27K—C28K | 1.549 (10) |
C25A—C26A | 1.518 (7) | C27L—C28L | 1.502 (9) |
C27A—C28A | 1.509 (7) | C29K—C30B | 1.526 (10) |
C29A—C30A | 1.497 (8) | C29L—C30B | 1.526 (9) |
C31A—C36A | 1.382 (8) | C31B—C36B | 1.399 (8) |
C31A—C32A | 1.397 (8) | C31B—C32B | 1.399 (7) |
C32A—C33A | 1.383 (9) | C32B—C33B | 1.385 (8) |
C32A—C58A | 1.509 (9) | C32B—C58B | 1.522 (8) |
C33A—C34A | 1.370 (10) | C33B—C34B | 1.371 (9) |
C34A—C35A | 1.398 (9) | C34B—C35B | 1.369 (9) |
C35A—C36A | 1.394 (8) | C35B—C36B | 1.384 (9) |
C36A—C37A | 1.506 (8) | C36B—C37B | 1.513 (8) |
C37A—C38A | 1.511 (8) | C37B—C38B | 1.519 (8) |
C38A—C39A | 1.384 (7) | C38B—C39B | 1.386 (8) |
C38A—C43A | 1.392 (7) | C38B—C43B | 1.391 (9) |
C39A—C40A | 1.393 (7) | C39B—C40B | 1.397 (8) |
C40A—C41A | 1.405 (8) | C40B—C41B | 1.373 (9) |
C40A—C44A | 1.506 (8) | C40B—C44B | 1.531 (9) |
C41A—C42A | 1.362 (9) | C41B—C42B | 1.376 (9) |
C42A—C43A | 1.385 (9) | C42B—C43B | 1.385 (9) |
C44A—C45A | 1.503 (8) | C44B—C45B | 1.519 (8) |
C45A—C50A | 1.383 (8) | C45B—C50B | 1.385 (8) |
C45A—C46A | 1.391 (7) | C45B—C46B | 1.396 (8) |
C46A—C47A | 1.390 (7) | C46B—C47B | 1.393 (7) |
C47A—C48A | 1.384 (8) | C47B—C48B | 1.384 (8) |
C47A—C51A | 1.520 (8) | C47B—C51B | 1.504 (8) |
C48A—C49A | 1.383 (10) | C48B—C49B | 1.378 (9) |
C49A—C50A | 1.376 (10) | C49B—C50B | 1.370 (9) |
C51A—C52A | 1.511 (8) | C51B—C52B | 1.514 (8) |
C52A—C57A | 1.380 (8) | C52B—C57B | 1.387 (8) |
C52A—C53A | 1.405 (8) | C52B—C53B | 1.390 (7) |
C53A—C54A | 1.396 (8) | C53B—C54B | 1.395 (8) |
C54A—C55A | 1.387 (9) | C54B—C55B | 1.387 (8) |
C54A—C58A | 1.521 (9) | C54B—C58B | 1.524 (8) |
C55A—C56A | 1.374 (9) | C55B—C56B | 1.371 (8) |
C56A—C57A | 1.375 (9) | C56B—C57B | 1.369 (8) |
O1B—C31B | 1.381 (6) | | |
| | | |
C31A—O1A—C1A | 113.6 (4) | C31B—O1B—C1B | 115.1 (4) |
C2A—O2A—C3A | 112.2 (5) | C2B—O2B—C3B | 114.1 (6) |
C5A—O3A—C4I | 120.0 (11) | C5B—O3B—C4B | 121.2 (6) |
C5A—O3A—C4J | 114.5 (4) | C14B—O4B—C17B | 115.6 (4) |
C14A—O4A—C17A | 121.0 (5) | C19B—O5B—C18B | 113.9 (4) |
C19A—O5A—C18A | 113.1 (4) | C46B—O6B—C20B | 115.1 (4) |
C46A—O6A—C20A | 114.2 (4) | C53B—O7B—C21B | 114.2 (4) |
C53A—O7A—C21I | 129.6 (6) | C22B—O8B—C23B | 117.2 (5) |
C53A—O7A—C21J | 104.5 (5) | C25B—O9K—C24K | 114.6 (8) |
C22I—O8I—C23I | 109.6 (7) | C24L—O9L—C25B | 121.3 (11) |
C23J—O8J—C22J | 112.1 (6) | C27K—O10K—C26K | 117.7 (11) |
C25A—O9I—C24I | 109.2 (7) | C27L—O10L—C26L | 113.6 (8) |
C24J—O9J—C25A | 114.9 (7) | C29K—O11K—C28K | 110.5 (9) |
C26A—O10A—C27A | 113.2 (5) | C29L—O11L—C28L | 111.1 (7) |
C29A—O11A—C28A | 114.4 (6) | C39B—O12B—C30B | 112.4 (5) |
C39A—O12A—C30A | 113.7 (4) | N2B—N1B—C8B | 113.7 (4) |
N2A—N1A—C8A | 114.5 (4) | N1B—N2B—C11B | 114.2 (4) |
N1A—N2A—C11A | 113.4 (4) | O1B—C1B—C2B | 109.7 (5) |
O1A—C1A—C2A | 113.9 (5) | O2B—C2B—C1B | 108.1 (6) |
O2A—C2A—C1A | 110.3 (5) | O2B—C3B—C4B | 113.8 (7) |
O2A—C3A—C4J | 108.0 (5) | O3B—C4B—C3B | 115.4 (7) |
O2A—C3A—C4I | 102.5 (10) | C10B—C5B—C6B | 119.6 (6) |
O3A—C4I—C3A | 115.7 (10) | C10B—C5B—O3B | 125.6 (6) |
O3A—C4J—C3A | 113.5 (5) | C6B—C5B—O3B | 114.8 (6) |
O3A—C5A—C6A | 120.7 (5) | C7B—C6B—C5B | 120.2 (6) |
O3A—C5A—C10A | 118.9 (5) | C6B—C7B—C8B | 120.9 (6) |
C6A—C5A—C10A | 120.3 (5) | C9B—C8B—C7B | 118.6 (5) |
C5A—C6A—C7A | 120.9 (5) | C9B—C8B—N1B | 116.6 (5) |
C6A—C7A—C8A | 119.5 (5) | C7B—C8B—N1B | 124.7 (5) |
C9A—C8A—C7A | 119.5 (5) | C8B—C9B—C10B | 120.9 (6) |
C9A—C8A—N1A | 115.9 (5) | C5B—C10B—C9B | 119.7 (6) |
C7A—C8A—N1A | 124.6 (5) | C16B—C11B—C12B | 118.8 (5) |
C8A—C9A—C10A | 120.9 (5) | C16B—C11B—N2B | 115.9 (5) |
C5A—C10A—C9A | 118.7 (5) | C12B—C11B—N2B | 125.2 (5) |
C16A—C11A—C12A | 119.1 (5) | C13B—C12B—C11B | 120.4 (5) |
C16A—C11A—N2A | 116.9 (5) | C12B—C13B—C14B | 120.1 (5) |
C12A—C11A—N2A | 123.9 (5) | C15B—C14B—O4B | 118.6 (5) |
C13A—C12A—C11A | 120.4 (5) | C15B—C14B—C13B | 120.2 (5) |
C12A—C13A—C14A | 119.8 (5) | O4B—C14B—C13B | 121.2 (5) |
O4A—C14A—C13A | 114.8 (5) | C14B—C15B—C16B | 119.2 (5) |
O4A—C14A—C15A | 124.8 (5) | C15B—C16B—C11B | 121.1 (5) |
C13A—C14A—C15A | 120.4 (5) | O4B—C17B—C18B | 111.5 (5) |
C14A—C15A—C16A | 118.5 (5) | O5B—C18B—C17B | 109.2 (5) |
C11A—C16A—C15A | 121.3 (5) | O5B—C19B—C20B | 110.3 (5) |
O4A—C17A—C18A | 115.4 (5) | O6B—C20B—C19B | 113.7 (5) |
O5A—C18A—C17A | 110.0 (5) | O7B—C21B—C22B | 110.4 (5) |
O5A—C19A—C20A | 108.6 (5) | O8B—C22B—C21B | 113.4 (6) |
O6A—C20A—C19A | 112.6 (5) | O8B—C23B—C24L | 102.9 (7) |
O7A—C21I—C22I | 117.4 (9) | O8B—C23B—C24K | 105.4 (7) |
O7A—C21J—C22J | 102.4 (6) | O9K—C24K—C23B | 110.1 (8) |
O8I—C22I—C21I | 108.7 (8) | O9L—C24L—C23B | 107.4 (11) |
O8J—C22J—C21J | 108.2 (6) | O9L—C25B—C26L | 138.9 (14) |
O8I—C23I—C24I | 104.8 (8) | O9K—C25B—C26K | 114.1 (16) |
O8J—C23J—C24J | 110.0 (8) | O10K—C26K—C25B | 106.0 (10) |
O9I—C24I—C23I | 107.7 (8) | O10L—C26L—C25B | 102.3 (8) |
O9J—C24J—C23J | 111.9 (8) | O10K—C27K—C28K | 106.0 (9) |
O9I—C25A—C26A | 101.7 (6) | O10L—C27L—C28L | 110.7 (8) |
O9J—C25A—C26A | 115.9 (6) | O11K—C28K—C27K | 106.8 (8) |
O10A—C26A—C25A | 109.5 (6) | O11L—C28L—C27L | 109.2 (8) |
O10A—C27A—C28A | 107.0 (6) | O11K—C29K—C30B | 104.1 (12) |
O11A—C28A—C27A | 105.4 (6) | O11L—C29L—C30B | 112.4 (8) |
O11A—C29A—C30A | 116.1 (6) | O12B—C30B—C29L | 108.8 (7) |
O12A—C30A—C29A | 110.4 (5) | O12B—C30B—C29K | 106.5 (11) |
C36A—C31A—O1A | 120.0 (5) | O1B—C31B—C36B | 118.3 (5) |
C36A—C31A—C32A | 123.1 (5) | O1B—C31B—C32B | 119.7 (5) |
O1A—C31A—C32A | 116.7 (5) | C36B—C31B—C32B | 121.8 (5) |
C33A—C32A—C31A | 117.6 (6) | C33B—C32B—C31B | 117.7 (5) |
C33A—C32A—C58A | 121.0 (6) | C33B—C32B—C58B | 121.0 (5) |
C31A—C32A—C58A | 121.3 (5) | C31B—C32B—C58B | 120.9 (5) |
C34A—C33A—C32A | 121.2 (6) | C34B—C33B—C32B | 120.8 (6) |
C33A—C34A—C35A | 119.8 (6) | C33B—C34B—C35B | 120.5 (6) |
C36A—C35A—C34A | 121.0 (6) | C34B—C35B—C36B | 121.2 (6) |
C31A—C36A—C35A | 116.9 (5) | C35B—C36B—C31B | 117.3 (5) |
C31A—C36A—C37A | 121.8 (5) | C35B—C36B—C37B | 121.8 (6) |
C35A—C36A—C37A | 120.8 (5) | C31B—C36B—C37B | 120.8 (5) |
C36A—C37A—C38A | 109.7 (4) | C36B—C37B—C38B | 112.0 (4) |
C39A—C38A—C43A | 117.7 (5) | C39B—C38B—C43B | 118.0 (6) |
C39A—C38A—C37A | 121.1 (5) | C39B—C38B—C37B | 120.2 (6) |
C43A—C38A—C37A | 120.8 (5) | C43B—C38B—C37B | 121.8 (6) |
C38A—C39A—C40A | 123.3 (5) | C38B—C39B—O12B | 118.4 (5) |
C38A—C39A—O12A | 117.8 (5) | C38B—C39B—C40B | 121.8 (6) |
C40A—C39A—O12A | 118.8 (5) | O12B—C39B—C40B | 119.8 (6) |
C39A—C40A—C41A | 116.4 (5) | C41B—C40B—C39B | 118.3 (6) |
C39A—C40A—C44A | 122.4 (5) | C41B—C40B—C44B | 120.3 (5) |
C41A—C40A—C44A | 121.0 (5) | C39B—C40B—C44B | 120.9 (6) |
C42A—C41A—C40A | 121.5 (6) | C40B—C41B—C42B | 121.3 (6) |
C41A—C42A—C43A | 120.5 (5) | C41B—C42B—C43B | 119.7 (7) |
C42A—C43A—C38A | 120.4 (6) | C42B—C43B—C38B | 120.8 (6) |
C45A—C44A—C40A | 111.4 (4) | C45B—C44B—C40B | 109.7 (5) |
C50A—C45A—C46A | 117.2 (5) | C50B—C45B—C46B | 118.0 (6) |
C50A—C45A—C44A | 120.6 (5) | C50B—C45B—C44B | 120.9 (6) |
C46A—C45A—C44A | 121.8 (5) | C46B—C45B—C44B | 120.8 (5) |
O6A—C46A—C47A | 119.5 (5) | O6B—C46B—C47B | 117.7 (5) |
O6A—C46A—C45A | 118.1 (5) | O6B—C46B—C45B | 119.9 (5) |
C47A—C46A—C45A | 122.3 (5) | C47B—C46B—C45B | 122.2 (5) |
C48A—C47A—C46A | 118.0 (6) | C48B—C47B—C46B | 117.4 (5) |
C48A—C47A—C51A | 120.7 (5) | C48B—C47B—C51B | 121.6 (5) |
C46A—C47A—C51A | 120.6 (5) | C46B—C47B—C51B | 120.9 (5) |
C49A—C48A—C47A | 120.7 (6) | C49B—C48B—C47B | 120.6 (6) |
C50A—C49A—C48A | 119.6 (6) | C50B—C49B—C48B | 121.3 (6) |
C49A—C50A—C45A | 121.7 (6) | C49B—C50B—C45B | 120.1 (6) |
C52A—C51A—C47A | 109.3 (4) | C47B—C51B—C52B | 111.9 (4) |
C57A—C52A—C53A | 118.0 (6) | C57B—C52B—C53B | 117.5 (5) |
C57A—C52A—C51A | 121.5 (6) | C57B—C52B—C51B | 121.2 (5) |
C53A—C52A—C51A | 119.9 (6) | C53B—C52B—C51B | 121.1 (5) |
O7A—C53A—C54A | 118.4 (6) | C52B—C53B—C54B | 122.3 (5) |
O7A—C53A—C52A | 120.4 (5) | C52B—C53B—O7B | 117.6 (5) |
C54A—C53A—C52A | 121.0 (6) | C54B—C53B—O7B | 120.0 (5) |
C55A—C54A—C53A | 118.5 (6) | C55B—C54B—C53B | 117.4 (5) |
C55A—C54A—C58A | 121.8 (5) | C55B—C54B—C58B | 120.2 (5) |
C53A—C54A—C58A | 119.4 (6) | C53B—C54B—C58B | 122.1 (5) |
C56A—C55A—C54A | 120.9 (6) | C56B—C55B—C54B | 121.1 (6) |
C55A—C56A—C57A | 120.1 (7) | C57B—C56B—C55B | 120.4 (6) |
C56A—C57A—C52A | 121.4 (6) | C56B—C57B—C52B | 121.1 (6) |
C32A—C58A—C54A | 111.9 (4) | C32B—C58B—C54B | 109.6 (4) |
Experimental details
| (1) | (2a) | (2b) |
Crystal data |
Chemical formula | C58H64N2O12 | C58H64N2O12 | C58H64N2O12 |
Mr | 981.11 | 981.11 | 981.11 |
Crystal system, space group | Monoclinic, P21/a | Monoclinic, P21/a | Triclinic, P1 |
Temperature (K) | 243 | 273 | 213 |
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), 90 | 90, 112.39 (2), 90 | 92.22 (3), 112.32 (2), 87.81 (3) |
V (Å3) | 5145 (4) | 5258 (3) | 5199 (3) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.70 × 0.60 × 0.50 | 0.65 × 0.60 × 0.50 | 0.65 × 0.60 × 0.50 |
|
Data collection |
Diffractometer | Enraf-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 |
Rint | 0.02 | 0.017 | 0.021 |
θmax (°) | 22 | 23 | 23 |
(sin θ/λ)max (Å−1) | 0.527 | 0.550 | 0.550 |
|
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 reflections | 4701 | 5696 | 12460 |
No. of parameters | 628 | 636 | 1290 |
No. of restraints | 79 | 75 | 104 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-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 Å−3) | 1.49, −0.60 | 0.56, −0.33 | 0.66, −0.50 |