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The one-step reaction of isophthaloyl dichloride with the 2-aminopyridine derivative (methyl 6-aminonicotinate) yields (i) a trimer-based macrocycle (EsIO)
3 and (ii) a tetramer-based macrocycle (EsIO)
4 in modest isolated synthetic yields (total of 25%), together with (iii) longer open-chain oligomers. The macrocyclization relies on the semi-flexible imide
hinge formed by reaction of the 2-amino(pyridine) functional group with two acyl chloride functional groups. The determining factors in macrocycle synthesis are: (
a) imide formation using the heteroaromatic
ortho-N functionality; (
b) the inherent ability of the imide to twist by 85–115° from planarity (as measured by the CO
CO imide torsion angles), thereby providing a
hinge for macrocyclic ring closure or potentially (non)helical assembly in oligomer/polymer formation; (
c) the conformational flexibility of the isophthaloyl group with
meta-related carbonyl groups to twist and adopt either
syn or
anti conformations, although the
syn conformation is observed structurally for all isophthaloyl groups in both (EsIO)
3 (trezimide) and (EsIO)
4 (tennimide) macrocycles.
Supporting information
For both compounds, data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Crystal data top
C60H40N8O16 | F(000) = 2336 |
Mr = 1129.00 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/n | Melting point: 476 K |
Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54184 Å |
a = 10.6870 (1) Å | Cell parameters from 11636 reflections |
b = 22.4852 (2) Å | θ = 2.8–63.1° |
c = 22.6756 (2) Å | µ = 0.88 mm−1 |
β = 101.721 (1)° | T = 294 K |
V = 5335.31 (8) Å3 | Needle, colourless |
Z = 4 | 0.58 × 0.06 × 0.05 mm |
Data collection top
Xcalibur, Sapphire3, Gemini Ultra diffractometer | 8619 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 6947 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 63.3°, θmin = 2.8° |
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998) | h = −11→12 |
Tmin = 0.631, Tmax = 0.958 | k = −24→25 |
31765 measured reflections | l = −26→21 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.1981P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
8619 reflections | Δρmax = 0.27 e Å−3 |
762 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00038 (5) |
Crystal data top
C60H40N8O16 | V = 5335.31 (8) Å3 |
Mr = 1129.00 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 10.6870 (1) Å | µ = 0.88 mm−1 |
b = 22.4852 (2) Å | T = 294 K |
c = 22.6756 (2) Å | 0.58 × 0.06 × 0.05 mm |
β = 101.721 (1)° | |
Data collection top
Xcalibur, Sapphire3, Gemini Ultra diffractometer | 8619 independent reflections |
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998) | 6947 reflections with I > 2σ(I) |
Tmin = 0.631, Tmax = 0.958 | Rint = 0.034 |
31765 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.27 e Å−3 |
8619 reflections | Δρmin = −0.17 e Å−3 |
762 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.15831 (17) | 0.18857 (7) | 0.46844 (7) | 0.0612 (4) | |
C1 | 0.2011 (2) | 0.18789 (9) | 0.42307 (9) | 0.0464 (5) | |
N1 | 0.30161 (16) | 0.22599 (8) | 0.41630 (7) | 0.0479 (4) | |
O2 | 0.45380 (16) | 0.28347 (9) | 0.47432 (8) | 0.0757 (5) | |
C2 | 0.3421 (2) | 0.27245 (10) | 0.45862 (9) | 0.0517 (5) | |
O3 | −0.07174 (15) | 0.44529 (6) | 0.39841 (7) | 0.0563 (4) | |
C3 | −0.05505 (19) | 0.39251 (9) | 0.40628 (9) | 0.0433 (4) | |
N2 | −0.13146 (15) | 0.35051 (7) | 0.36964 (7) | 0.0427 (4) | |
O4 | −0.31578 (15) | 0.34468 (8) | 0.29957 (9) | 0.0745 (5) | |
C4 | −0.21277 (18) | 0.36745 (9) | 0.31491 (10) | 0.0459 (5) | |
O5 | 0.14918 (15) | 0.44217 (8) | 0.15956 (7) | 0.0620 (4) | |
C5 | 0.13048 (19) | 0.43811 (8) | 0.21004 (9) | 0.0413 (4) | |
N3 | 0.23290 (14) | 0.42727 (7) | 0.25862 (7) | 0.0393 (4) | |
O6 | 0.44817 (13) | 0.43474 (7) | 0.26451 (7) | 0.0571 (4) | |
C6 | 0.35088 (18) | 0.40900 (8) | 0.24366 (9) | 0.0408 (4) | |
O7 | 0.24172 (16) | 0.15482 (6) | 0.18935 (8) | 0.0616 (4) | |
C7 | 0.1926 (2) | 0.20376 (8) | 0.18419 (9) | 0.0436 (4) | |
N4 | 0.06544 (15) | 0.20986 (7) | 0.18926 (7) | 0.0405 (4) | |
O8 | −0.07996 (16) | 0.13342 (7) | 0.17083 (7) | 0.0669 (5) | |
C8 | 0.00609 (19) | 0.15568 (8) | 0.20559 (9) | 0.0444 (5) | |
C11 | 0.05471 (19) | 0.13301 (8) | 0.26695 (9) | 0.0417 (4) | |
C12 | 0.11227 (18) | 0.17018 (8) | 0.31334 (8) | 0.0407 (4) | |
H12 | 0.1274 | 0.2098 | 0.3055 | 0.049* | |
C13 | 0.14713 (19) | 0.14824 (9) | 0.37129 (9) | 0.0438 (4) | |
C14 | 0.1284 (2) | 0.08870 (9) | 0.38258 (10) | 0.0553 (5) | |
H14 | 0.1524 | 0.0739 | 0.4215 | 0.066* | |
C15 | 0.0743 (3) | 0.05144 (10) | 0.33620 (11) | 0.0645 (7) | |
H15 | 0.0635 | 0.0113 | 0.3438 | 0.077* | |
C16 | 0.0359 (2) | 0.07337 (9) | 0.27849 (10) | 0.0549 (5) | |
H16 | −0.0024 | 0.0483 | 0.2474 | 0.066* | |
C11A | 0.38579 (19) | 0.21038 (9) | 0.37715 (9) | 0.0463 (5) | |
N12A | 0.40890 (18) | 0.15260 (8) | 0.37348 (8) | 0.0527 (4) | |
C13A | 0.4729 (2) | 0.13613 (10) | 0.33154 (10) | 0.0535 (5) | |
H13A | 0.4867 | 0.0957 | 0.3268 | 0.064* | |
C14A | 0.52007 (19) | 0.17554 (9) | 0.29475 (10) | 0.0491 (5) | |
C15A | 0.5028 (2) | 0.23589 (10) | 0.30320 (10) | 0.0539 (5) | |
H15A | 0.5382 | 0.2638 | 0.2811 | 0.065* | |
C16A | 0.4330 (2) | 0.25374 (10) | 0.34449 (10) | 0.0526 (5) | |
H16A | 0.4178 | 0.2938 | 0.3503 | 0.063* | |
O1A | 0.6420 (2) | 0.18734 (9) | 0.21920 (11) | 0.1021 (8) | |
C1A | 0.5839 (2) | 0.15541 (11) | 0.24621 (11) | 0.0603 (6) | |
C2A | 0.6155 (3) | 0.07496 (14) | 0.18517 (13) | 0.0856 (9) | |
H2A1 | 0.5775 | 0.0957 | 0.1490 | 0.128* | |
H2A2 | 0.5962 | 0.0333 | 0.1803 | 0.128* | |
H2A3 | 0.7064 | 0.0805 | 0.1931 | 0.128* | |
O2A | 0.56501 (18) | 0.09792 (7) | 0.23468 (8) | 0.0699 (5) | |
C21 | 0.2427 (2) | 0.30939 (9) | 0.47743 (9) | 0.0479 (5) | |
C22 | 0.13017 (19) | 0.32416 (8) | 0.43767 (9) | 0.0430 (4) | |
H22 | 0.1075 | 0.3044 | 0.4011 | 0.052* | |
C23 | 0.05146 (19) | 0.36851 (9) | 0.45256 (9) | 0.0458 (5) | |
C24 | 0.0838 (2) | 0.39644 (12) | 0.50825 (11) | 0.0659 (6) | |
H24 | 0.0319 | 0.4264 | 0.5184 | 0.079* | |
C25 | 0.1930 (3) | 0.37971 (14) | 0.54847 (11) | 0.0771 (8) | |
H25 | 0.2127 | 0.3974 | 0.5863 | 0.093* | |
C26 | 0.2731 (2) | 0.33695 (12) | 0.53308 (10) | 0.0645 (6) | |
H26 | 0.3476 | 0.3266 | 0.5601 | 0.077* | |
C21A | −0.16031 (18) | 0.29351 (8) | 0.39325 (9) | 0.0410 (4) | |
N22A | −0.13026 (16) | 0.24697 (7) | 0.36253 (8) | 0.0481 (4) | |
C23A | −0.1622 (2) | 0.19371 (9) | 0.38118 (10) | 0.0476 (5) | |
H23A | −0.1432 | 0.1603 | 0.3604 | 0.057* | |
C24A | −0.22132 (19) | 0.18503 (8) | 0.42920 (9) | 0.0428 (4) | |
C25A | −0.2507 (2) | 0.23456 (9) | 0.46015 (10) | 0.0512 (5) | |
H25A | −0.2906 | 0.2305 | 0.4927 | 0.061* | |
C26A | −0.2190 (2) | 0.29017 (9) | 0.44140 (10) | 0.0528 (5) | |
H26A | −0.2373 | 0.3244 | 0.4611 | 0.063* | |
O3A | −0.2326 (2) | 0.08049 (7) | 0.41664 (8) | 0.0762 (5) | |
C3A | −0.2554 (2) | 0.12334 (9) | 0.44377 (10) | 0.0489 (5) | |
C4A | −0.3591 (4) | 0.06359 (12) | 0.50494 (16) | 0.0993 (12) | |
H4A1 | −0.4373 | 0.0538 | 0.4775 | 0.149* | |
H4A2 | −0.3738 | 0.0647 | 0.5453 | 0.149* | |
H4A3 | −0.2957 | 0.0340 | 0.5022 | 0.149* | |
O4A | −0.3145 (2) | 0.12144 (7) | 0.48944 (8) | 0.0736 (5) | |
C31 | −0.16309 (17) | 0.40963 (8) | 0.27486 (9) | 0.0396 (4) | |
C32 | −0.03647 (17) | 0.40921 (8) | 0.26872 (8) | 0.0384 (4) | |
H32 | 0.0238 | 0.3870 | 0.2951 | 0.046* | |
C33 | −0.00017 (18) | 0.44204 (8) | 0.22318 (8) | 0.0384 (4) | |
C34 | −0.09054 (19) | 0.47605 (9) | 0.18452 (9) | 0.0450 (5) | |
H34 | −0.0669 | 0.4971 | 0.1532 | 0.054* | |
C35 | −0.21488 (19) | 0.47864 (9) | 0.19256 (10) | 0.0489 (5) | |
H35 | −0.2738 | 0.5032 | 0.1682 | 0.059* | |
C36 | −0.25167 (19) | 0.44482 (9) | 0.23679 (9) | 0.0466 (5) | |
H36 | −0.3363 | 0.4455 | 0.2412 | 0.056* | |
C31A | 0.24288 (17) | 0.45518 (8) | 0.31615 (9) | 0.0393 (4) | |
N32A | 0.29189 (17) | 0.42068 (7) | 0.36269 (7) | 0.0471 (4) | |
C33A | 0.3098 (2) | 0.44536 (9) | 0.41730 (9) | 0.0501 (5) | |
H33A | 0.3464 | 0.4223 | 0.4504 | 0.060* | |
C34A | 0.2766 (2) | 0.50355 (9) | 0.42736 (10) | 0.0479 (5) | |
C35A | 0.2243 (2) | 0.53745 (9) | 0.37797 (10) | 0.0554 (5) | |
H35A | 0.1994 | 0.5764 | 0.3831 | 0.067* | |
C36A | 0.2088 (2) | 0.51362 (9) | 0.32106 (10) | 0.0506 (5) | |
H36A | 0.1765 | 0.5363 | 0.2871 | 0.061* | |
O5A | 0.2480 (2) | 0.57656 (9) | 0.49846 (9) | 0.0932 (7) | |
C5A | 0.2945 (2) | 0.53020 (11) | 0.48872 (11) | 0.0589 (6) | |
C6A | 0.3814 (3) | 0.51744 (16) | 0.59240 (12) | 0.0906 (10) | |
H6A1 | 0.4135 | 0.5574 | 0.5948 | 0.136* | |
H6A2 | 0.4409 | 0.4922 | 0.6184 | 0.136* | |
H6A3 | 0.3006 | 0.5166 | 0.6047 | 0.136* | |
O6A | 0.36492 (18) | 0.49632 (9) | 0.53073 (8) | 0.0727 (5) | |
C41 | 0.34559 (18) | 0.35574 (8) | 0.20463 (9) | 0.0412 (4) | |
C42 | 0.26049 (17) | 0.30969 (8) | 0.20754 (8) | 0.0387 (4) | |
H42 | 0.1986 | 0.3137 | 0.2308 | 0.046* | |
C43 | 0.26811 (18) | 0.25763 (8) | 0.17566 (9) | 0.0414 (4) | |
C44 | 0.3569 (2) | 0.25264 (10) | 0.13941 (10) | 0.0534 (5) | |
H44 | 0.3623 | 0.2176 | 0.1183 | 0.064* | |
C45 | 0.4379 (2) | 0.29944 (11) | 0.13421 (11) | 0.0611 (6) | |
H45 | 0.4945 | 0.2967 | 0.1081 | 0.073* | |
C46 | 0.4342 (2) | 0.35029 (10) | 0.16793 (10) | 0.0514 (5) | |
H46 | 0.4914 | 0.3811 | 0.1660 | 0.062* | |
C41A | −0.01798 (18) | 0.25496 (8) | 0.15947 (8) | 0.0393 (4) | |
N42A | 0.01418 (15) | 0.27914 (7) | 0.11119 (7) | 0.0450 (4) | |
C43A | −0.06151 (19) | 0.32277 (9) | 0.08422 (9) | 0.0461 (5) | |
H43A | −0.0391 | 0.3416 | 0.0514 | 0.055* | |
C44A | −0.17069 (18) | 0.34142 (8) | 0.10229 (8) | 0.0414 (4) | |
C45A | −0.2031 (2) | 0.31376 (9) | 0.15181 (9) | 0.0470 (5) | |
H45A | −0.2773 | 0.3245 | 0.1646 | 0.056* | |
C46A | −0.12450 (19) | 0.27053 (9) | 0.18160 (9) | 0.0460 (5) | |
H46A | −0.1424 | 0.2522 | 0.2157 | 0.055* | |
O7A | −0.21082 (15) | 0.42144 (7) | 0.03253 (7) | 0.0601 (4) | |
C7A | −0.2484 (2) | 0.38948 (9) | 0.06763 (9) | 0.0451 (5) | |
C8A | −0.4476 (3) | 0.43701 (13) | 0.04686 (12) | 0.0743 (8) | |
H8A1 | −0.4071 | 0.4753 | 0.0526 | 0.112* | |
H8A2 | −0.5266 | 0.4382 | 0.0608 | 0.112* | |
H8A3 | −0.4643 | 0.4269 | 0.0048 | 0.112* | |
O8A | −0.36477 (14) | 0.39304 (7) | 0.08034 (7) | 0.0562 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0883 (12) | 0.0569 (9) | 0.0402 (8) | −0.0023 (8) | 0.0177 (8) | 0.0020 (7) |
C1 | 0.0572 (12) | 0.0431 (11) | 0.0373 (11) | 0.0079 (9) | 0.0058 (9) | 0.0059 (8) |
N1 | 0.0537 (10) | 0.0470 (9) | 0.0398 (9) | 0.0027 (8) | 0.0019 (8) | −0.0055 (7) |
O2 | 0.0506 (10) | 0.0993 (14) | 0.0687 (11) | 0.0036 (9) | −0.0076 (8) | −0.0306 (10) |
C2 | 0.0536 (13) | 0.0560 (13) | 0.0393 (11) | 0.0045 (10) | −0.0052 (9) | −0.0036 (9) |
O3 | 0.0702 (10) | 0.0384 (8) | 0.0591 (9) | 0.0002 (7) | 0.0103 (8) | −0.0013 (7) |
C3 | 0.0476 (11) | 0.0402 (11) | 0.0441 (11) | −0.0022 (8) | 0.0138 (9) | −0.0011 (8) |
N2 | 0.0426 (9) | 0.0374 (8) | 0.0463 (9) | −0.0031 (7) | 0.0049 (7) | 0.0058 (7) |
O4 | 0.0444 (9) | 0.0718 (11) | 0.0969 (13) | −0.0200 (8) | −0.0104 (8) | 0.0328 (10) |
C4 | 0.0370 (11) | 0.0410 (10) | 0.0571 (13) | −0.0020 (8) | 0.0036 (9) | 0.0065 (9) |
O5 | 0.0600 (10) | 0.0840 (11) | 0.0443 (9) | 0.0131 (8) | 0.0164 (7) | 0.0142 (8) |
C5 | 0.0449 (11) | 0.0393 (10) | 0.0397 (11) | 0.0012 (8) | 0.0091 (8) | 0.0026 (8) |
N3 | 0.0365 (8) | 0.0402 (8) | 0.0412 (9) | −0.0009 (6) | 0.0083 (7) | −0.0042 (7) |
O6 | 0.0410 (8) | 0.0557 (9) | 0.0762 (11) | −0.0101 (7) | 0.0157 (7) | −0.0162 (8) |
C6 | 0.0384 (10) | 0.0390 (10) | 0.0460 (11) | −0.0034 (8) | 0.0112 (8) | 0.0006 (8) |
O7 | 0.0690 (10) | 0.0387 (8) | 0.0800 (11) | 0.0105 (7) | 0.0222 (8) | −0.0017 (7) |
C7 | 0.0524 (12) | 0.0388 (11) | 0.0382 (10) | 0.0037 (9) | 0.0057 (9) | −0.0027 (8) |
N4 | 0.0430 (9) | 0.0344 (8) | 0.0410 (9) | −0.0014 (7) | 0.0015 (7) | 0.0055 (6) |
O8 | 0.0757 (11) | 0.0550 (9) | 0.0570 (10) | −0.0229 (8) | −0.0171 (8) | 0.0085 (7) |
C8 | 0.0502 (11) | 0.0371 (10) | 0.0417 (11) | −0.0047 (9) | −0.0007 (9) | 0.0012 (8) |
C11 | 0.0466 (11) | 0.0367 (10) | 0.0402 (10) | −0.0009 (8) | 0.0049 (8) | 0.0036 (8) |
C12 | 0.0446 (11) | 0.0345 (9) | 0.0419 (11) | 0.0013 (8) | 0.0057 (8) | 0.0036 (8) |
C13 | 0.0506 (11) | 0.0425 (10) | 0.0370 (10) | 0.0030 (9) | 0.0061 (9) | 0.0023 (8) |
C14 | 0.0763 (15) | 0.0465 (12) | 0.0406 (12) | 0.0013 (11) | 0.0061 (10) | 0.0095 (9) |
C15 | 0.0992 (19) | 0.0371 (11) | 0.0534 (14) | −0.0091 (11) | 0.0067 (13) | 0.0091 (10) |
C16 | 0.0753 (15) | 0.0370 (11) | 0.0485 (12) | −0.0083 (10) | 0.0032 (11) | 0.0017 (9) |
C11A | 0.0474 (11) | 0.0476 (12) | 0.0399 (11) | 0.0034 (9) | −0.0007 (9) | −0.0020 (9) |
N12A | 0.0602 (11) | 0.0467 (10) | 0.0518 (11) | 0.0089 (8) | 0.0130 (9) | 0.0052 (8) |
C13A | 0.0570 (13) | 0.0463 (12) | 0.0581 (13) | 0.0070 (10) | 0.0143 (11) | 0.0034 (10) |
C14A | 0.0421 (11) | 0.0515 (12) | 0.0516 (12) | 0.0003 (9) | 0.0047 (9) | 0.0011 (9) |
C15A | 0.0526 (12) | 0.0526 (13) | 0.0541 (13) | −0.0098 (10) | 0.0052 (10) | 0.0044 (10) |
C16A | 0.0586 (13) | 0.0443 (11) | 0.0518 (13) | −0.0018 (10) | 0.0036 (10) | −0.0012 (9) |
O1A | 0.1188 (18) | 0.0823 (14) | 0.1288 (19) | −0.0153 (12) | 0.0811 (16) | 0.0038 (13) |
C1A | 0.0551 (13) | 0.0645 (15) | 0.0644 (15) | −0.0024 (11) | 0.0196 (11) | 0.0064 (12) |
C2A | 0.106 (2) | 0.088 (2) | 0.0753 (19) | 0.0105 (17) | 0.0476 (17) | −0.0042 (15) |
O2A | 0.0875 (12) | 0.0603 (10) | 0.0710 (11) | 0.0001 (9) | 0.0373 (10) | −0.0038 (8) |
C21 | 0.0535 (12) | 0.0501 (11) | 0.0370 (11) | 0.0013 (9) | 0.0017 (9) | −0.0027 (9) |
C22 | 0.0501 (11) | 0.0432 (11) | 0.0337 (10) | −0.0045 (9) | 0.0041 (8) | −0.0031 (8) |
C23 | 0.0490 (11) | 0.0474 (11) | 0.0404 (11) | −0.0026 (9) | 0.0076 (9) | −0.0036 (9) |
C24 | 0.0662 (15) | 0.0788 (17) | 0.0531 (14) | 0.0086 (13) | 0.0132 (12) | −0.0201 (12) |
C25 | 0.0755 (17) | 0.109 (2) | 0.0427 (13) | 0.0112 (16) | 0.0021 (12) | −0.0270 (14) |
C26 | 0.0652 (15) | 0.0843 (17) | 0.0387 (12) | 0.0099 (13) | −0.0018 (10) | −0.0101 (11) |
C21A | 0.0393 (10) | 0.0373 (10) | 0.0451 (11) | −0.0017 (8) | 0.0058 (8) | 0.0038 (8) |
N22A | 0.0517 (10) | 0.0426 (9) | 0.0527 (10) | −0.0038 (7) | 0.0171 (8) | −0.0013 (8) |
C23A | 0.0529 (12) | 0.0386 (10) | 0.0534 (12) | −0.0004 (9) | 0.0162 (10) | −0.0045 (9) |
C24A | 0.0460 (11) | 0.0371 (10) | 0.0436 (11) | 0.0005 (8) | 0.0049 (9) | 0.0016 (8) |
C25A | 0.0692 (14) | 0.0419 (11) | 0.0469 (12) | −0.0006 (10) | 0.0225 (10) | 0.0009 (9) |
C26A | 0.0711 (14) | 0.0366 (11) | 0.0552 (13) | −0.0022 (10) | 0.0235 (11) | −0.0050 (9) |
O3A | 0.1179 (15) | 0.0405 (9) | 0.0817 (12) | −0.0066 (9) | 0.0473 (11) | −0.0070 (8) |
C3A | 0.0585 (13) | 0.0400 (11) | 0.0484 (12) | −0.0002 (9) | 0.0115 (10) | 0.0013 (9) |
C4A | 0.158 (3) | 0.0497 (15) | 0.111 (3) | −0.0145 (17) | 0.077 (2) | 0.0125 (15) |
O4A | 0.1177 (15) | 0.0417 (8) | 0.0746 (11) | −0.0040 (9) | 0.0503 (11) | 0.0041 (8) |
C31 | 0.0361 (10) | 0.0372 (10) | 0.0430 (11) | −0.0016 (7) | 0.0020 (8) | 0.0017 (8) |
C32 | 0.0369 (10) | 0.0365 (9) | 0.0387 (10) | 0.0010 (7) | 0.0002 (8) | 0.0012 (8) |
C33 | 0.0384 (10) | 0.0371 (9) | 0.0379 (10) | −0.0015 (8) | 0.0031 (8) | −0.0025 (8) |
C34 | 0.0481 (11) | 0.0418 (11) | 0.0425 (11) | −0.0007 (8) | 0.0032 (9) | 0.0053 (8) |
C35 | 0.0433 (11) | 0.0469 (11) | 0.0514 (12) | 0.0065 (9) | −0.0023 (9) | 0.0102 (9) |
C36 | 0.0340 (10) | 0.0471 (11) | 0.0556 (13) | 0.0016 (8) | 0.0018 (9) | 0.0045 (9) |
C31A | 0.0356 (10) | 0.0388 (10) | 0.0435 (11) | −0.0035 (8) | 0.0079 (8) | −0.0022 (8) |
N32A | 0.0568 (10) | 0.0389 (9) | 0.0443 (10) | 0.0038 (7) | 0.0073 (8) | −0.0026 (7) |
C33A | 0.0595 (13) | 0.0466 (11) | 0.0427 (11) | 0.0021 (9) | 0.0067 (10) | −0.0034 (9) |
C34A | 0.0516 (12) | 0.0444 (11) | 0.0495 (12) | −0.0061 (9) | 0.0145 (9) | −0.0089 (9) |
C35A | 0.0682 (14) | 0.0384 (11) | 0.0609 (14) | 0.0028 (10) | 0.0160 (11) | −0.0097 (10) |
C36A | 0.0571 (13) | 0.0396 (11) | 0.0541 (13) | 0.0036 (9) | 0.0087 (10) | 0.0017 (9) |
O5A | 0.1380 (19) | 0.0680 (12) | 0.0766 (13) | 0.0156 (12) | 0.0285 (13) | −0.0255 (10) |
C5A | 0.0647 (15) | 0.0589 (14) | 0.0568 (14) | −0.0084 (12) | 0.0214 (12) | −0.0161 (11) |
C6A | 0.084 (2) | 0.132 (3) | 0.0532 (16) | −0.0015 (19) | 0.0090 (14) | −0.0286 (17) |
O6A | 0.0762 (11) | 0.0894 (13) | 0.0500 (10) | 0.0063 (10) | 0.0070 (8) | −0.0193 (9) |
C41 | 0.0393 (10) | 0.0420 (10) | 0.0424 (11) | 0.0007 (8) | 0.0083 (8) | −0.0008 (8) |
C42 | 0.0381 (10) | 0.0408 (10) | 0.0379 (10) | 0.0034 (8) | 0.0091 (8) | 0.0007 (8) |
C43 | 0.0406 (10) | 0.0407 (10) | 0.0409 (10) | 0.0012 (8) | 0.0033 (8) | −0.0012 (8) |
C44 | 0.0557 (13) | 0.0538 (12) | 0.0523 (13) | 0.0028 (10) | 0.0150 (10) | −0.0127 (10) |
C45 | 0.0570 (14) | 0.0724 (15) | 0.0612 (14) | −0.0060 (11) | 0.0291 (11) | −0.0132 (12) |
C46 | 0.0450 (11) | 0.0558 (12) | 0.0570 (13) | −0.0068 (9) | 0.0190 (10) | −0.0065 (10) |
C41A | 0.0452 (11) | 0.0350 (9) | 0.0345 (10) | −0.0039 (8) | 0.0003 (8) | 0.0004 (7) |
N42A | 0.0453 (9) | 0.0480 (9) | 0.0408 (9) | 0.0018 (7) | 0.0065 (7) | 0.0061 (7) |
C43A | 0.0499 (12) | 0.0448 (11) | 0.0417 (11) | −0.0014 (9) | 0.0046 (9) | 0.0110 (9) |
C44A | 0.0419 (10) | 0.0396 (10) | 0.0390 (10) | −0.0018 (8) | −0.0004 (8) | 0.0012 (8) |
C45A | 0.0454 (11) | 0.0497 (11) | 0.0448 (11) | 0.0033 (9) | 0.0065 (9) | 0.0024 (9) |
C46A | 0.0496 (12) | 0.0482 (11) | 0.0398 (11) | 0.0000 (9) | 0.0084 (9) | 0.0086 (9) |
O7A | 0.0687 (10) | 0.0498 (9) | 0.0595 (10) | 0.0010 (7) | 0.0077 (8) | 0.0163 (7) |
C7A | 0.0520 (12) | 0.0398 (10) | 0.0400 (11) | 0.0012 (9) | 0.0008 (9) | −0.0004 (9) |
C8A | 0.0709 (16) | 0.0835 (18) | 0.0655 (16) | 0.0344 (14) | 0.0065 (13) | 0.0175 (14) |
O8A | 0.0560 (9) | 0.0600 (9) | 0.0504 (9) | 0.0153 (7) | 0.0060 (7) | 0.0096 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.208 (2) | N22A—C23A | 1.337 (3) |
C1—N1 | 1.407 (3) | C23A—C24A | 1.380 (3) |
C1—C13 | 1.494 (3) | C23A—H23A | 0.9300 |
N1—C2 | 1.425 (3) | C24A—C25A | 1.386 (3) |
N1—C11A | 1.430 (3) | C24A—C3A | 1.488 (3) |
O2—C2 | 1.201 (3) | C25A—C26A | 1.384 (3) |
C2—C21 | 1.478 (3) | C25A—H25A | 0.9300 |
O3—C3 | 1.208 (2) | C26A—H26A | 0.9300 |
C3—N2 | 1.405 (3) | O3A—C3A | 1.195 (3) |
C3—C23 | 1.484 (3) | C3A—O4A | 1.319 (3) |
N2—C4 | 1.415 (3) | C4A—O4A | 1.453 (3) |
N2—C21A | 1.446 (2) | C4A—H4A1 | 0.9600 |
O4—C4 | 1.200 (2) | C4A—H4A2 | 0.9600 |
C4—C31 | 1.484 (3) | C4A—H4A3 | 0.9600 |
O5—C5 | 1.205 (2) | C31—C32 | 1.388 (3) |
C5—N3 | 1.407 (2) | C31—C36 | 1.391 (3) |
C5—C33 | 1.488 (3) | C32—C33 | 1.387 (3) |
N3—C6 | 1.431 (2) | C32—H32 | 0.9300 |
N3—C31A | 1.432 (2) | C33—C34 | 1.394 (3) |
O6—C6 | 1.200 (2) | C34—C35 | 1.379 (3) |
C6—C41 | 1.483 (3) | C34—H34 | 0.9300 |
O7—C7 | 1.215 (2) | C35—C36 | 1.378 (3) |
C7—N4 | 1.393 (3) | C35—H35 | 0.9300 |
C7—C43 | 1.490 (3) | C36—H36 | 0.9300 |
N4—C41A | 1.427 (2) | C31A—N32A | 1.329 (3) |
N4—C8 | 1.456 (2) | C31A—C36A | 1.374 (3) |
O8—C8 | 1.193 (2) | N32A—C33A | 1.335 (3) |
C8—C11 | 1.474 (3) | C33A—C34A | 1.386 (3) |
C11—C12 | 1.386 (3) | C33A—H33A | 0.9300 |
C11—C16 | 1.389 (3) | C34A—C35A | 1.376 (3) |
C12—C13 | 1.382 (3) | C34A—C5A | 1.491 (3) |
C12—H12 | 0.9300 | C35A—C36A | 1.376 (3) |
C13—C14 | 1.385 (3) | C35A—H35A | 0.9300 |
C14—C15 | 1.377 (3) | C36A—H36A | 0.9300 |
C14—H14 | 0.9300 | O5A—C5A | 1.194 (3) |
C15—C16 | 1.380 (3) | C5A—O6A | 1.328 (3) |
C15—H15 | 0.9300 | C6A—O6A | 1.453 (3) |
C16—H16 | 0.9300 | C6A—H6A1 | 0.9600 |
C11A—N12A | 1.328 (3) | C6A—H6A2 | 0.9600 |
C11A—C16A | 1.380 (3) | C6A—H6A3 | 0.9600 |
N12A—C13A | 1.332 (3) | C41—C46 | 1.388 (3) |
C13A—C14A | 1.380 (3) | C41—C42 | 1.389 (3) |
C13A—H13A | 0.9300 | C42—C43 | 1.387 (3) |
C14A—C15A | 1.388 (3) | C42—H42 | 0.9300 |
C14A—C1A | 1.479 (3) | C43—C44 | 1.381 (3) |
C15A—C16A | 1.371 (3) | C44—C45 | 1.382 (3) |
C15A—H15A | 0.9300 | C44—H44 | 0.9300 |
C16A—H16A | 0.9300 | C45—C46 | 1.381 (3) |
O1A—C1A | 1.196 (3) | C45—H45 | 0.9300 |
C1A—O2A | 1.326 (3) | C46—H46 | 0.9300 |
C2A—O2A | 1.437 (3) | C41A—N42A | 1.328 (2) |
C2A—H2A1 | 0.9600 | C41A—C46A | 1.379 (3) |
C2A—H2A2 | 0.9600 | N42A—C43A | 1.338 (2) |
C2A—H2A3 | 0.9600 | C43A—C44A | 1.378 (3) |
C21—C26 | 1.384 (3) | C43A—H43A | 0.9300 |
C21—C22 | 1.388 (3) | C44A—C45A | 1.388 (3) |
C22—C23 | 1.390 (3) | C44A—C7A | 1.487 (3) |
C22—H22 | 0.9300 | C45A—C46A | 1.370 (3) |
C23—C24 | 1.390 (3) | C45A—H45A | 0.9300 |
C24—C25 | 1.380 (4) | C46A—H46A | 0.9300 |
C24—H24 | 0.9300 | O7A—C7A | 1.201 (2) |
C25—C26 | 1.378 (4) | C7A—O8A | 1.334 (2) |
C25—H25 | 0.9300 | C8A—O8A | 1.437 (3) |
C26—H26 | 0.9300 | C8A—H8A1 | 0.9600 |
C21A—N22A | 1.332 (3) | C8A—H8A2 | 0.9600 |
C21A—C26A | 1.367 (3) | C8A—H8A3 | 0.9600 |
| | | |
O1—C1—N1 | 120.98 (19) | C23A—C24A—C3A | 118.63 (18) |
O1—C1—C13 | 121.7 (2) | C25A—C24A—C3A | 123.09 (18) |
N1—C1—C13 | 117.33 (17) | C26A—C25A—C24A | 118.41 (19) |
C1—N1—C2 | 120.45 (17) | C26A—C25A—H25A | 120.8 |
C1—N1—C11A | 120.60 (17) | C24A—C25A—H25A | 120.8 |
C2—N1—C11A | 117.07 (17) | C21A—C26A—C25A | 118.38 (19) |
O2—C2—N1 | 119.9 (2) | C21A—C26A—H26A | 120.8 |
O2—C2—C21 | 121.9 (2) | C25A—C26A—H26A | 120.8 |
N1—C2—C21 | 117.97 (18) | O3A—C3A—O4A | 123.96 (19) |
O3—C3—N2 | 121.49 (19) | O3A—C3A—C24A | 123.6 (2) |
O3—C3—C23 | 122.06 (19) | O4A—C3A—C24A | 112.47 (17) |
N2—C3—C23 | 116.35 (17) | O4A—C4A—H4A1 | 109.5 |
C3—N2—C4 | 121.16 (16) | O4A—C4A—H4A2 | 109.5 |
C3—N2—C21A | 121.25 (16) | H4A1—C4A—H4A2 | 109.5 |
C4—N2—C21A | 115.10 (15) | O4A—C4A—H4A3 | 109.5 |
O4—C4—N2 | 120.22 (18) | H4A1—C4A—H4A3 | 109.5 |
O4—C4—C31 | 121.10 (19) | H4A2—C4A—H4A3 | 109.5 |
N2—C4—C31 | 118.46 (16) | C3A—O4A—C4A | 116.87 (19) |
O5—C5—N3 | 120.27 (18) | C32—C31—C36 | 119.73 (18) |
O5—C5—C33 | 121.95 (18) | C32—C31—C4 | 122.29 (17) |
N3—C5—C33 | 117.74 (16) | C36—C31—C4 | 117.41 (17) |
C5—N3—C6 | 116.53 (15) | C33—C32—C31 | 119.78 (17) |
C5—N3—C31A | 122.64 (15) | C33—C32—H32 | 120.1 |
C6—N3—C31A | 115.83 (15) | C31—C32—H32 | 120.1 |
O6—C6—N3 | 120.18 (17) | C32—C33—C34 | 119.83 (18) |
O6—C6—C41 | 123.34 (18) | C32—C33—C5 | 122.21 (17) |
N3—C6—C41 | 116.40 (16) | C34—C33—C5 | 117.71 (17) |
O7—C7—N4 | 119.41 (18) | C35—C34—C33 | 120.22 (18) |
O7—C7—C43 | 120.93 (19) | C35—C34—H34 | 119.9 |
N4—C7—C43 | 119.59 (16) | C33—C34—H34 | 119.9 |
C7—N4—C41A | 123.85 (15) | C36—C35—C34 | 119.88 (18) |
C7—N4—C8 | 114.91 (15) | C36—C35—H35 | 120.1 |
C41A—N4—C8 | 116.92 (15) | C34—C35—H35 | 120.1 |
O8—C8—N4 | 120.03 (18) | C35—C36—C31 | 120.45 (18) |
O8—C8—C11 | 123.73 (18) | C35—C36—H36 | 119.8 |
N4—C8—C11 | 116.18 (16) | C31—C36—H36 | 119.8 |
C12—C11—C16 | 119.87 (18) | N32A—C31A—C36A | 124.21 (18) |
C12—C11—C8 | 121.68 (17) | N32A—C31A—N3 | 114.33 (16) |
C16—C11—C8 | 118.37 (18) | C36A—C31A—N3 | 121.40 (18) |
C13—C12—C11 | 119.93 (18) | C31A—N32A—C33A | 116.94 (17) |
C13—C12—H12 | 120.0 | N32A—C33A—C34A | 123.5 (2) |
C11—C12—H12 | 120.0 | N32A—C33A—H33A | 118.2 |
C12—C13—C14 | 119.98 (19) | C34A—C33A—H33A | 118.2 |
C12—C13—C1 | 121.39 (17) | C35A—C34A—C33A | 117.65 (19) |
C14—C13—C1 | 118.60 (18) | C35A—C34A—C5A | 119.4 (2) |
C15—C14—C13 | 120.06 (19) | C33A—C34A—C5A | 123.0 (2) |
C15—C14—H14 | 120.0 | C36A—C35A—C34A | 119.93 (19) |
C13—C14—H14 | 120.0 | C36A—C35A—H35A | 120.0 |
C14—C15—C16 | 120.3 (2) | C34A—C35A—H35A | 120.0 |
C14—C15—H15 | 119.8 | C31A—C36A—C35A | 117.7 (2) |
C16—C15—H15 | 119.8 | C31A—C36A—H36A | 121.1 |
C15—C16—C11 | 119.8 (2) | C35A—C36A—H36A | 121.1 |
C15—C16—H16 | 120.1 | O5A—C5A—O6A | 124.4 (2) |
C11—C16—H16 | 120.1 | O5A—C5A—C34A | 123.0 (2) |
N12A—C11A—C16A | 124.4 (2) | O6A—C5A—C34A | 112.7 (2) |
N12A—C11A—N1 | 115.30 (18) | O6A—C6A—H6A1 | 109.5 |
C16A—C11A—N1 | 120.28 (18) | O6A—C6A—H6A2 | 109.5 |
C11A—N12A—C13A | 116.48 (19) | H6A1—C6A—H6A2 | 109.5 |
N12A—C13A—C14A | 123.8 (2) | O6A—C6A—H6A3 | 109.5 |
N12A—C13A—H13A | 118.1 | H6A1—C6A—H6A3 | 109.5 |
C14A—C13A—H13A | 118.1 | H6A2—C6A—H6A3 | 109.5 |
C13A—C14A—C15A | 118.0 (2) | C5A—O6A—C6A | 116.3 (2) |
C13A—C14A—C1A | 122.2 (2) | C46—C41—C42 | 119.74 (18) |
C15A—C14A—C1A | 119.8 (2) | C46—C41—C6 | 118.76 (17) |
C16A—C15A—C14A | 119.1 (2) | C42—C41—C6 | 121.32 (17) |
C16A—C15A—H15A | 120.4 | C43—C42—C41 | 119.77 (17) |
C14A—C15A—H15A | 120.4 | C43—C42—H42 | 120.1 |
C15A—C16A—C11A | 117.9 (2) | C41—C42—H42 | 120.1 |
C15A—C16A—H16A | 121.0 | C44—C43—C42 | 119.93 (18) |
C11A—C16A—H16A | 121.0 | C44—C43—C7 | 117.87 (17) |
O1A—C1A—O2A | 123.9 (2) | C42—C43—C7 | 121.86 (17) |
O1A—C1A—C14A | 124.3 (2) | C43—C44—C45 | 120.46 (19) |
O2A—C1A—C14A | 111.72 (19) | C43—C44—H44 | 119.8 |
O2A—C2A—H2A1 | 109.5 | C45—C44—H44 | 119.8 |
O2A—C2A—H2A2 | 109.5 | C46—C45—C44 | 119.6 (2) |
H2A1—C2A—H2A2 | 109.5 | C46—C45—H45 | 120.2 |
O2A—C2A—H2A3 | 109.5 | C44—C45—H45 | 120.2 |
H2A1—C2A—H2A3 | 109.5 | C45—C46—C41 | 120.3 (2) |
H2A2—C2A—H2A3 | 109.5 | C45—C46—H46 | 119.8 |
C1A—O2A—C2A | 116.0 (2) | C41—C46—H46 | 119.8 |
C26—C21—C22 | 119.8 (2) | N42A—C41A—C46A | 124.53 (18) |
C26—C21—C2 | 117.73 (19) | N42A—C41A—N4 | 116.09 (17) |
C22—C21—C2 | 121.68 (18) | C46A—C41A—N4 | 119.38 (17) |
C21—C22—C23 | 120.05 (18) | C41A—N42A—C43A | 116.30 (17) |
C21—C22—H22 | 120.0 | N42A—C43A—C44A | 123.86 (18) |
C23—C22—H22 | 120.0 | N42A—C43A—H43A | 118.1 |
C22—C23—C24 | 119.6 (2) | C44A—C43A—H43A | 118.1 |
C22—C23—C3 | 120.28 (17) | C43A—C44A—C45A | 118.01 (18) |
C24—C23—C3 | 119.43 (19) | C43A—C44A—C7A | 118.69 (17) |
C25—C24—C23 | 119.9 (2) | C45A—C44A—C7A | 123.29 (18) |
C25—C24—H24 | 120.1 | C46A—C45A—C44A | 119.22 (19) |
C23—C24—H24 | 120.1 | C46A—C45A—H45A | 120.4 |
C26—C25—C24 | 120.6 (2) | C44A—C45A—H45A | 120.4 |
C26—C25—H25 | 119.7 | C45A—C46A—C41A | 117.99 (18) |
C24—C25—H25 | 119.7 | C45A—C46A—H46A | 121.0 |
C25—C26—C21 | 120.0 (2) | C41A—C46A—H46A | 121.0 |
C25—C26—H26 | 120.0 | O7A—C7A—O8A | 124.01 (19) |
C21—C26—H26 | 120.0 | O7A—C7A—C44A | 123.98 (19) |
N22A—C21A—C26A | 124.94 (18) | O8A—C7A—C44A | 112.00 (17) |
N22A—C21A—N2 | 114.24 (17) | O8A—C8A—H8A1 | 109.5 |
C26A—C21A—N2 | 120.75 (17) | O8A—C8A—H8A2 | 109.5 |
C21A—N22A—C23A | 115.74 (17) | H8A1—C8A—H8A2 | 109.5 |
N22A—C23A—C24A | 124.31 (18) | O8A—C8A—H8A3 | 109.5 |
N22A—C23A—H23A | 117.8 | H8A1—C8A—H8A3 | 109.5 |
C24A—C23A—H23A | 117.8 | H8A2—C8A—H8A3 | 109.5 |
C23A—C24A—C25A | 118.23 (18) | C7A—O8A—C8A | 115.33 (18) |
| | | |
O1—C1—N1—C2 | −9.7 (3) | C26A—C21A—N22A—C23A | 0.5 (3) |
C13—C1—N1—C2 | 168.39 (17) | N2—C21A—N22A—C23A | −176.45 (17) |
O1—C1—N1—C11A | 154.23 (19) | C21A—N22A—C23A—C24A | −0.6 (3) |
C13—C1—N1—C11A | −27.7 (3) | N22A—C23A—C24A—C25A | 0.4 (3) |
C1—N1—C2—O2 | 140.5 (2) | N22A—C23A—C24A—C3A | 178.0 (2) |
C11A—N1—C2—O2 | −24.0 (3) | C23A—C24A—C25A—C26A | −0.1 (3) |
C1—N1—C2—C21 | −45.2 (3) | C3A—C24A—C25A—C26A | −177.5 (2) |
C11A—N1—C2—C21 | 150.33 (19) | N22A—C21A—C26A—C25A | −0.2 (3) |
O3—C3—N2—C4 | 13.2 (3) | N2—C21A—C26A—C25A | 176.57 (19) |
C23—C3—N2—C4 | −163.31 (17) | C24A—C25A—C26A—C21A | 0.0 (3) |
O3—C3—N2—C21A | −148.00 (19) | C23A—C24A—C3A—O3A | 1.2 (3) |
C23—C3—N2—C21A | 35.5 (2) | C25A—C24A—C3A—O3A | 178.6 (2) |
C3—N2—C4—O4 | −142.5 (2) | C23A—C24A—C3A—O4A | −178.2 (2) |
C21A—N2—C4—O4 | 19.8 (3) | C25A—C24A—C3A—O4A | −0.8 (3) |
C3—N2—C4—C31 | 42.9 (3) | O3A—C3A—O4A—C4A | −3.1 (4) |
C21A—N2—C4—C31 | −154.83 (17) | C24A—C3A—O4A—C4A | 176.3 (2) |
O5—C5—N3—C6 | −13.0 (3) | O4—C4—C31—C32 | −139.2 (2) |
C33—C5—N3—C6 | 164.84 (16) | N2—C4—C31—C32 | 35.4 (3) |
O5—C5—N3—C31A | 140.89 (19) | O4—C4—C31—C36 | 32.2 (3) |
C33—C5—N3—C31A | −41.3 (2) | N2—C4—C31—C36 | −153.30 (19) |
C5—N3—C6—O6 | 127.8 (2) | C36—C31—C32—C33 | −2.5 (3) |
C31A—N3—C6—O6 | −27.9 (3) | C4—C31—C32—C33 | 168.61 (18) |
C5—N3—C6—C41 | −55.4 (2) | C31—C32—C33—C34 | 1.1 (3) |
C31A—N3—C6—C41 | 148.91 (17) | C31—C32—C33—C5 | −173.04 (17) |
O7—C7—N4—C41A | −150.95 (19) | O5—C5—C33—C32 | 145.4 (2) |
C43—C7—N4—C41A | 32.1 (3) | N3—C5—C33—C32 | −32.4 (3) |
O7—C7—N4—C8 | 4.9 (3) | O5—C5—C33—C34 | −28.9 (3) |
C43—C7—N4—C8 | −172.03 (17) | N3—C5—C33—C34 | 153.35 (17) |
C7—N4—C8—O8 | −114.6 (2) | C32—C33—C34—C35 | 2.0 (3) |
C41A—N4—C8—O8 | 43.0 (3) | C5—C33—C34—C35 | 176.44 (18) |
C7—N4—C8—C11 | 68.0 (2) | C33—C34—C35—C36 | −3.7 (3) |
C41A—N4—C8—C11 | −134.40 (18) | C34—C35—C36—C31 | 2.3 (3) |
O8—C8—C11—C12 | −152.3 (2) | C32—C31—C36—C35 | 0.8 (3) |
N4—C8—C11—C12 | 24.9 (3) | C4—C31—C36—C35 | −170.72 (19) |
O8—C8—C11—C16 | 24.5 (3) | C5—N3—C31A—N32A | 143.78 (18) |
N4—C8—C11—C16 | −158.29 (19) | C6—N3—C31A—N32A | −62.2 (2) |
C16—C11—C12—C13 | −2.0 (3) | C5—N3—C31A—C36A | −38.9 (3) |
C8—C11—C12—C13 | 174.68 (19) | C6—N3—C31A—C36A | 115.2 (2) |
C11—C12—C13—C14 | 2.1 (3) | C36A—C31A—N32A—C33A | −0.7 (3) |
C11—C12—C13—C1 | −175.73 (18) | N3—C31A—N32A—C33A | 176.55 (17) |
O1—C1—C13—C12 | 128.9 (2) | C31A—N32A—C33A—C34A | 1.9 (3) |
N1—C1—C13—C12 | −49.2 (3) | N32A—C33A—C34A—C35A | −0.9 (3) |
O1—C1—C13—C14 | −49.0 (3) | N32A—C33A—C34A—C5A | 178.6 (2) |
N1—C1—C13—C14 | 132.9 (2) | C33A—C34A—C35A—C36A | −1.2 (3) |
C12—C13—C14—C15 | −0.4 (3) | C5A—C34A—C35A—C36A | 179.2 (2) |
C1—C13—C14—C15 | 177.5 (2) | N32A—C31A—C36A—C35A | −1.3 (3) |
C13—C14—C15—C16 | −1.4 (4) | N3—C31A—C36A—C35A | −178.44 (19) |
C14—C15—C16—C11 | 1.5 (4) | C34A—C35A—C36A—C31A | 2.3 (3) |
C12—C11—C16—C15 | 0.2 (3) | C35A—C34A—C5A—O5A | 11.9 (4) |
C8—C11—C16—C15 | −176.6 (2) | C33A—C34A—C5A—O5A | −167.7 (2) |
C1—N1—C11A—N12A | −33.3 (3) | C35A—C34A—C5A—O6A | −169.3 (2) |
C2—N1—C11A—N12A | 131.2 (2) | C33A—C34A—C5A—O6A | 11.1 (3) |
C1—N1—C11A—C16A | 144.1 (2) | O5A—C5A—O6A—C6A | 2.0 (4) |
C2—N1—C11A—C16A | −51.4 (3) | C34A—C5A—O6A—C6A | −176.8 (2) |
C16A—C11A—N12A—C13A | −5.9 (3) | O6—C6—C41—C46 | −31.0 (3) |
N1—C11A—N12A—C13A | 171.38 (18) | N3—C6—C41—C46 | 152.34 (18) |
C11A—N12A—C13A—C14A | 3.1 (3) | O6—C6—C41—C42 | 144.2 (2) |
N12A—C13A—C14A—C15A | 1.9 (3) | N3—C6—C41—C42 | −32.5 (3) |
N12A—C13A—C14A—C1A | −176.2 (2) | C46—C41—C42—C43 | 2.6 (3) |
C13A—C14A—C15A—C16A | −4.3 (3) | C6—C41—C42—C43 | −172.50 (18) |
C1A—C14A—C15A—C16A | 173.9 (2) | C41—C42—C43—C44 | −2.5 (3) |
C14A—C15A—C16A—C11A | 1.8 (3) | C41—C42—C43—C7 | 170.79 (18) |
N12A—C11A—C16A—C15A | 3.6 (3) | O7—C7—C43—C44 | 38.6 (3) |
N1—C11A—C16A—C15A | −173.61 (19) | N4—C7—C43—C44 | −144.54 (19) |
C13A—C14A—C1A—O1A | −168.7 (3) | O7—C7—C43—C42 | −134.8 (2) |
C15A—C14A—C1A—O1A | 13.2 (4) | N4—C7—C43—C42 | 42.1 (3) |
C13A—C14A—C1A—O2A | 13.6 (3) | C42—C43—C44—C45 | −0.5 (3) |
C15A—C14A—C1A—O2A | −164.5 (2) | C7—C43—C44—C45 | −174.1 (2) |
O1A—C1A—O2A—C2A | −2.1 (4) | C43—C44—C45—C46 | 3.4 (4) |
C14A—C1A—O2A—C2A | 175.6 (2) | C44—C45—C46—C41 | −3.2 (4) |
O2—C2—C21—C26 | −31.0 (3) | C42—C41—C46—C45 | 0.2 (3) |
N1—C2—C21—C26 | 154.7 (2) | C6—C41—C46—C45 | 175.4 (2) |
O2—C2—C21—C22 | 138.8 (2) | C7—N4—C41A—N42A | 21.8 (3) |
N1—C2—C21—C22 | −35.4 (3) | C8—N4—C41A—N42A | −133.57 (18) |
C26—C21—C22—C23 | 3.1 (3) | C7—N4—C41A—C46A | −158.30 (18) |
C2—C21—C22—C23 | −166.5 (2) | C8—N4—C41A—C46A | 46.3 (2) |
C21—C22—C23—C24 | −2.2 (3) | C46A—C41A—N42A—C43A | 2.2 (3) |
C21—C22—C23—C3 | 168.33 (19) | N4—C41A—N42A—C43A | −177.94 (16) |
O3—C3—C23—C22 | −131.0 (2) | C41A—N42A—C43A—C44A | −2.7 (3) |
N2—C3—C23—C22 | 45.5 (3) | N42A—C43A—C44A—C45A | 0.8 (3) |
O3—C3—C23—C24 | 39.6 (3) | N42A—C43A—C44A—C7A | −178.57 (18) |
N2—C3—C23—C24 | −143.9 (2) | C43A—C44A—C45A—C46A | 1.7 (3) |
C22—C23—C24—C25 | −0.5 (4) | C7A—C44A—C45A—C46A | −178.94 (19) |
C3—C23—C24—C25 | −171.1 (2) | C44A—C45A—C46A—C41A | −2.2 (3) |
C23—C24—C25—C26 | 2.4 (4) | N42A—C41A—C46A—C45A | 0.2 (3) |
C24—C25—C26—C21 | −1.6 (5) | N4—C41A—C46A—C45A | −179.66 (17) |
C22—C21—C26—C25 | −1.2 (4) | C43A—C44A—C7A—O7A | −15.5 (3) |
C2—C21—C26—C25 | 168.8 (3) | C45A—C44A—C7A—O7A | 165.2 (2) |
C3—N2—C21A—N22A | −125.4 (2) | C43A—C44A—C7A—O8A | 164.78 (17) |
C4—N2—C21A—N22A | 72.3 (2) | C45A—C44A—C7A—O8A | −14.6 (3) |
C3—N2—C21A—C26A | 57.5 (3) | O7A—C7A—O8A—C8A | 2.6 (3) |
C4—N2—C21A—C26A | −104.8 (2) | C44A—C7A—O8A—C8A | −177.70 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A2···O5i | 0.96 | 2.56 | 3.491 (4) | 165 |
C6A—H6A3···O3ii | 0.96 | 2.58 | 3.461 (4) | 153 |
C26A—H26A···O5Aii | 0.93 | 2.42 | 3.333 (3) | 167 |
C15A—H15A···O4iii | 0.93 | 2.38 | 3.133 (3) | 138 |
C35A—H35A···O7iv | 0.93 | 2.57 | 3.107 (3) | 117 |
C36—H36···O6v | 0.93 | 2.48 | 3.400 (2) | 171 |
C12—H12···N4 | 0.93 | 2.58 | 2.897 (2) | 100 |
C13A—H13A···O2A | 0.93 | 2.40 | 2.722 (3) | 100 |
C23A—H23A···O3A | 0.93 | 2.50 | 2.818 (3) | 100 |
C33A—H33A···O6A | 0.93 | 2.45 | 2.768 (3) | 100 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) x−1, y, z. |
(EsIO3_II_12-015_Squeeze)
top
Crystal data top
C45H30N6O12 | Z = 4 |
Mr = 846.75 | F(000) = 1752 |
Triclinic, P1 | Dx = 1.197 Mg m−3 |
Hall symbol: -P 1 | Melting point: 490 K |
a = 16.3411 (13) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 16.5747 (4) Å | Cell parameters from 784 reflections |
c = 17.4806 (16) Å | θ = 2.5–51.9° |
α = 87.273 (5)° | µ = 0.75 mm−1 |
β = 83.350 (7)° | T = 294 K |
γ = 89.825 (4)° | Lath, colourless |
V = 4697.4 (6) Å3 | 0.60 × 0.08 × 0.02 mm |
Data collection top
Xcalibur, Sapphire3, Gemini Ultra diffractometer | 10048 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 4137 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
ω scans | θmax = 51.4°, θmin = 2.6° |
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998) | h = −16→16 |
Tmin = 0.663, Tmax = 0.989 | k = −16→16 |
16648 measured reflections | l = −17→17 |
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)] = 0.121 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.352 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.1927P)2] where P = (Fo2 + 2Fc2)/3 |
10048 reflections | (Δ/σ)max < 0.001 |
1141 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Crystal data top
C45H30N6O12 | γ = 89.825 (4)° |
Mr = 846.75 | V = 4697.4 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 16.3411 (13) Å | Cu Kα radiation |
b = 16.5747 (4) Å | µ = 0.75 mm−1 |
c = 17.4806 (16) Å | T = 294 K |
α = 87.273 (5)° | 0.60 × 0.08 × 0.02 mm |
β = 83.350 (7)° | |
Data collection top
Xcalibur, Sapphire3, Gemini Ultra diffractometer | 10048 independent reflections |
Absorption correction: analytical (ABSFAC, Clark and Reid, 1998) | 4137 reflections with I > 2σ(I) |
Tmin = 0.663, Tmax = 0.989 | Rint = 0.083 |
16648 measured reflections | θmax = 51.4° |
Refinement top
R[F2 > 2σ(F2)] = 0.121 | 0 restraints |
wR(F2) = 0.352 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.47 e Å−3 |
10048 reflections | Δρmin = −0.35 e Å−3 |
1141 parameters | |
Special details top
Experimental. Crystals of (EsIO)3 grow as fragile thin laths that diffracted very weakly. The first attempt with Mo radiation gave a unit cell and diffraction data to 2.5 Angstroms, whereas a second data collection gave reflection data to a 1.5 Angstroms limit [data were collected to 0.94 Angstroms resolution with Cu radiation, 1 degree omega scans with the detector at 60 mm and with shells collected for 16s\48s\48 s]. This was not sufficient to produce a structural solution. The data redundancy were 1.7, F2 = 2.1 and Rint 0.156. Finally on a third attempt and with data collected at 40 kV40mA over 72 h, reflection data were collected with a diffraction limit of 1.35 Angstroms to a resolution limit of 1.00 Angstroms with 0.5 degree scans, and shells collected with 24 s, 48 s and the detector at 60 mm. This 3rd dataset has a redundancy = 1.8, F2 = 4.3 and Rint 0.083 and this was sufficient to get a solution with a moderate direct methods attempt. The crystal size = 0.02 x 0.08 x 0.45 mm. It was apparent at an intermediate stage of refinement that there were considerable voids in the lattice and amounting to 21% of the unit cell and containing solvent molecules of unknown composition and occupancy. The program Squeeze was used and the R-factor dropped from 18% to 12% after implementation of this program. The FMLS refinement proceeded without any problems or use of restraints to give a satisfactory (EsIO)3 structure (II) with Z'=2. There are small but significant differences between the two molecules. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.2228 (5) | 0.1200 (4) | 0.8399 (5) | 0.092 (2) | |
C1A | 0.2783 (7) | 0.1529 (7) | 0.8633 (6) | 0.077 (3) | |
N1 | 0.2813 (5) | 0.2399 (4) | 0.8644 (5) | 0.070 (2) | |
O2A | 0.1973 (4) | 0.3425 (4) | 0.8332 (4) | 0.095 (2) | |
C2A | 0.2380 (6) | 0.2836 (6) | 0.8106 (7) | 0.079 (3) | |
O3A | 0.4657 (6) | 0.2004 (5) | 0.5448 (5) | 0.117 (3) | |
C3A | 0.4121 (9) | 0.1689 (7) | 0.5919 (7) | 0.094 (4) | |
N2 | 0.4155 (5) | 0.0920 (6) | 0.6183 (5) | 0.081 (2) | |
O4A | 0.4894 (5) | −0.0203 (5) | 0.5949 (5) | 0.119 (3) | |
C4A | 0.4907 (8) | 0.0515 (8) | 0.6092 (6) | 0.091 (3) | |
O5A | 0.6810 (4) | 0.2856 (4) | 0.7672 (4) | 0.094 (2) | |
C5A | 0.6413 (6) | 0.2246 (6) | 0.7708 (6) | 0.069 (3) | |
N3 | 0.5935 (5) | 0.1998 (4) | 0.8392 (5) | 0.070 (2) | |
O6A | 0.6379 (5) | 0.0658 (4) | 0.8466 (5) | 0.105 (3) | |
C6A | 0.5806 (7) | 0.1115 (6) | 0.8568 (5) | 0.073 (3) | |
C11 | 0.4934 (6) | 0.0893 (5) | 0.8811 (5) | 0.057 (2) | |
C12 | 0.4265 (6) | 0.1372 (5) | 0.8726 (5) | 0.063 (2) | |
H12 | 0.4348 | 0.1909 | 0.8556 | 0.075* | |
C13 | 0.3465 (5) | 0.1080 (5) | 0.8886 (5) | 0.059 (2) | |
C14 | 0.3325 (6) | 0.0282 (5) | 0.9186 (5) | 0.069 (3) | |
H14 | 0.2795 | 0.0071 | 0.9281 | 0.083* | |
C15 | 0.4008 (7) | −0.0181 (5) | 0.9336 (6) | 0.078 (3) | |
H15 | 0.3926 | −0.0685 | 0.9592 | 0.093* | |
C16 | 0.4792 (7) | 0.0088 (6) | 0.9117 (6) | 0.081 (3) | |
H16 | 0.5236 | −0.0256 | 0.9167 | 0.097* | |
C11A | 0.2930 (6) | 0.2726 (7) | 0.9344 (7) | 0.075 (3) | |
N12A | 0.2685 (5) | 0.2340 (5) | 0.9994 (6) | 0.078 (2) | |
C13A | 0.2741 (6) | 0.2675 (6) | 1.0656 (7) | 0.075 (3) | |
H13A | 0.2586 | 0.2387 | 1.1120 | 0.090* | |
C14A | 0.3036 (6) | 0.3467 (6) | 1.0655 (7) | 0.072 (3) | |
C15A | 0.3323 (6) | 0.3864 (7) | 0.9966 (8) | 0.085 (3) | |
H15A | 0.3526 | 0.4388 | 0.9957 | 0.102* | |
C16A | 0.3306 (6) | 0.3495 (7) | 0.9327 (7) | 0.080 (3) | |
H16A | 0.3540 | 0.3735 | 0.8862 | 0.097* | |
C17A | 0.2938 (6) | 0.3869 (8) | 1.1425 (9) | 0.086 (3) | |
O11A | 0.2856 (6) | 0.3495 (6) | 1.2028 (6) | 0.119 (3) | |
O12A | 0.3010 (5) | 0.4648 (5) | 1.1359 (5) | 0.113 (3) | |
C18A | 0.2859 (10) | 0.5080 (9) | 1.2107 (10) | 0.172 (7) | |
H18A | 0.3061 | 0.4755 | 1.2514 | 0.258* | |
H18B | 0.2279 | 0.5169 | 1.2230 | 0.258* | |
H18C | 0.3142 | 0.5590 | 1.2050 | 0.258* | |
C21 | 0.2527 (6) | 0.2670 (5) | 0.7280 (6) | 0.068 (3) | |
C22 | 0.3193 (6) | 0.2220 (6) | 0.7008 (6) | 0.078 (3) | |
H22 | 0.3522 | 0.1958 | 0.7341 | 0.094* | |
C23 | 0.3359 (6) | 0.2172 (7) | 0.6204 (7) | 0.086 (3) | |
C24 | 0.2870 (8) | 0.2594 (7) | 0.5734 (7) | 0.094 (3) | |
H24 | 0.3012 | 0.2599 | 0.5203 | 0.113* | |
C25 | 0.2193 (9) | 0.2998 (8) | 0.6012 (8) | 0.114 (4) | |
H25 | 0.1848 | 0.3231 | 0.5677 | 0.136* | |
C26 | 0.2022 (7) | 0.3062 (7) | 0.6769 (8) | 0.099 (4) | |
H26 | 0.1570 | 0.3364 | 0.6963 | 0.119* | |
C21A | 0.3410 (8) | 0.0461 (7) | 0.6329 (8) | 0.096 (3) | |
N22A | 0.2927 (7) | 0.0478 (6) | 0.5785 (5) | 0.099 (3) | |
C23A | 0.2259 (8) | 0.0041 (8) | 0.5906 (6) | 0.098 (3) | |
H23A | 0.1936 | 0.0013 | 0.5504 | 0.117* | |
C24A | 0.1989 (8) | −0.0392 (7) | 0.6603 (8) | 0.093 (4) | |
C25A | 0.2472 (10) | −0.0394 (7) | 0.7154 (10) | 0.114 (5) | |
H25A | 0.2317 | −0.0684 | 0.7616 | 0.137* | |
C26A | 0.3195 (10) | 0.0021 (7) | 0.7060 (7) | 0.103 (4) | |
H26A | 0.3537 | 0.0023 | 0.7449 | 0.123* | |
C27A | 0.1226 (9) | −0.0883 (9) | 0.6749 (11) | 0.113 (4) | |
O21A | 0.1048 (7) | −0.1296 (7) | 0.7297 (7) | 0.156 (4) | |
O22A | 0.0769 (6) | −0.0733 (6) | 0.6166 (7) | 0.139 (3) | |
C28A | 0.0046 (13) | −0.1212 (12) | 0.6184 (12) | 0.226 (11) | |
H28A | −0.0045 | −0.1517 | 0.6668 | 0.339* | |
H28B | 0.0111 | −0.1575 | 0.5770 | 0.339* | |
H28C | −0.0419 | −0.0867 | 0.6128 | 0.339* | |
C31 | 0.5685 (7) | 0.0902 (7) | 0.6248 (7) | 0.089 (3) | |
C32 | 0.5680 (7) | 0.1393 (6) | 0.6865 (6) | 0.081 (3) | |
H32 | 0.5182 | 0.1499 | 0.7156 | 0.098* | |
C33 | 0.6419 (7) | 0.1745 (6) | 0.7069 (7) | 0.081 (3) | |
C34 | 0.7123 (8) | 0.1630 (8) | 0.6553 (8) | 0.101 (4) | |
H34 | 0.7599 | 0.1916 | 0.6607 | 0.121* | |
C35 | 0.7129 (9) | 0.1118 (9) | 0.5985 (8) | 0.114 (4) | |
H35 | 0.7630 | 0.1003 | 0.5703 | 0.137* | |
C36 | 0.6433 (8) | 0.0754 (8) | 0.5797 (7) | 0.106 (4) | |
H36 | 0.6455 | 0.0419 | 0.5383 | 0.127* | |
C31A | 0.5759 (5) | 0.2482 (6) | 0.9031 (6) | 0.060 (2) | |
N32A | 0.5689 (5) | 0.2094 (5) | 0.9693 (5) | 0.075 (2) | |
C33A | 0.5478 (6) | 0.2537 (7) | 1.0338 (6) | 0.080 (3) | |
H33A | 0.5378 | 0.2261 | 1.0816 | 0.096* | |
C34A | 0.5410 (6) | 0.3363 (7) | 1.0307 (7) | 0.079 (3) | |
C35A | 0.5479 (6) | 0.3756 (6) | 0.9581 (7) | 0.081 (3) | |
H35A | 0.5415 | 0.4313 | 0.9533 | 0.097* | |
C36A | 0.5647 (7) | 0.3301 (7) | 0.8918 (7) | 0.093 (3) | |
H36A | 0.5681 | 0.3545 | 0.8425 | 0.112* | |
C37A | 0.5228 (8) | 0.3821 (10) | 1.1030 (9) | 0.098 (4) | |
O31A | 0.5236 (7) | 0.4546 (6) | 1.0991 (6) | 0.143 (4) | |
O32A | 0.5062 (4) | 0.3366 (5) | 1.1639 (6) | 0.104 (2) | |
C38A | 0.4941 (8) | 0.3777 (8) | 1.2346 (8) | 0.113 (4) | |
H38A | 0.5086 | 0.4337 | 1.2247 | 0.169* | |
H38B | 0.5283 | 0.3537 | 1.2706 | 0.169* | |
H38C | 0.4374 | 0.3734 | 1.2559 | 0.169* | |
O1B | 0.6815 (5) | 0.3806 (4) | 0.1606 (5) | 0.093 (2) | |
C1B | 0.7450 (7) | 0.3486 (5) | 0.1364 (6) | 0.069 (3) | |
N4 | 0.7461 (4) | 0.2615 (4) | 0.1340 (4) | 0.0625 (19) | |
O2B | 0.6536 (4) | 0.1608 (5) | 0.1637 (4) | 0.089 (2) | |
C2B | 0.6905 (7) | 0.2170 (7) | 0.1854 (6) | 0.075 (3) | |
O3B | 0.8543 (6) | 0.2858 (5) | 0.4513 (5) | 0.111 (3) | |
C3B | 0.8088 (7) | 0.3171 (8) | 0.4099 (7) | 0.088 (3) | |
N5 | 0.8263 (5) | 0.4005 (5) | 0.3822 (5) | 0.077 (2) | |
O4B | 0.8929 (5) | 0.5117 (5) | 0.4141 (5) | 0.119 (3) | |
C4B | 0.8987 (6) | 0.4482 (9) | 0.3942 (7) | 0.100 (4) | |
O5B | 1.1283 (4) | 0.2107 (4) | 0.2273 (4) | 0.089 (2) | |
C5B | 1.0870 (6) | 0.2740 (6) | 0.2262 (6) | 0.072 (3) | |
N6 | 1.0560 (4) | 0.2991 (4) | 0.1613 (5) | 0.068 (2) | |
O6B | 1.0991 (5) | 0.4303 (4) | 0.1530 (4) | 0.094 (2) | |
C6B | 1.0460 (6) | 0.3841 (5) | 0.1419 (6) | 0.068 (3) | |
C41 | 0.9662 (6) | 0.4111 (5) | 0.1173 (5) | 0.065 (2) | |
C42 | 0.8964 (6) | 0.3618 (5) | 0.1281 (5) | 0.062 (2) | |
H42 | 0.9004 | 0.3085 | 0.1465 | 0.074* | |
C43 | 0.8211 (6) | 0.3922 (6) | 0.1114 (6) | 0.071 (3) | |
C44 | 0.8146 (7) | 0.4725 (6) | 0.0797 (6) | 0.077 (3) | |
H44 | 0.7645 | 0.4932 | 0.0676 | 0.092* | |
C45 | 0.8871 (7) | 0.5194 (6) | 0.0675 (6) | 0.087 (3) | |
H45 | 0.8852 | 0.5715 | 0.0456 | 0.104* | |
C46 | 0.9611 (7) | 0.4889 (6) | 0.0877 (5) | 0.075 (3) | |
H46 | 1.0078 | 0.5216 | 0.0811 | 0.090* | |
C41A | 0.7774 (6) | 0.2300 (6) | 0.0642 (7) | 0.072 (3) | |
N42A | 0.7671 (4) | 0.2677 (5) | −0.0012 (6) | 0.073 (2) | |
C43A | 0.7881 (5) | 0.2341 (6) | −0.0640 (7) | 0.071 (3) | |
H43A | 0.7835 | 0.2641 | −0.1096 | 0.085* | |
C44A | 0.8182 (5) | 0.1535 (6) | −0.0700 (7) | 0.067 (3) | |
C45A | 0.8317 (6) | 0.1165 (6) | −0.0023 (8) | 0.082 (3) | |
H45A | 0.8537 | 0.0647 | −0.0025 | 0.098* | |
C46A | 0.8145 (6) | 0.1516 (6) | 0.0655 (6) | 0.073 (3) | |
H46A | 0.8262 | 0.1259 | 0.1115 | 0.088* | |
C47A | 0.8321 (6) | 0.1154 (7) | −0.1432 (8) | 0.078 (3) | |
O41A | 0.8352 (5) | 0.1519 (6) | −0.2059 (6) | 0.116 (3) | |
O42A | 0.8330 (5) | 0.0380 (5) | −0.1362 (5) | 0.115 (3) | |
C48A | 0.8378 (10) | −0.0074 (9) | −0.2086 (9) | 0.154 (6) | |
H48A | 0.8622 | 0.0265 | −0.2513 | 0.232* | |
H48B | 0.7833 | −0.0229 | −0.2178 | 0.232* | |
H48C | 0.8708 | −0.0548 | −0.2033 | 0.232* | |
C51 | 0.6854 (6) | 0.2355 (5) | 0.2690 (6) | 0.072 (3) | |
C52 | 0.7439 (6) | 0.2750 (6) | 0.3016 (6) | 0.073 (3) | |
H52 | 0.7860 | 0.3009 | 0.2692 | 0.088* | |
C53 | 0.7447 (6) | 0.2789 (6) | 0.3780 (6) | 0.072 (3) | |
C54 | 0.6787 (7) | 0.2413 (7) | 0.4272 (6) | 0.088 (3) | |
H54 | 0.6772 | 0.2431 | 0.4804 | 0.105* | |
C55 | 0.6162 (8) | 0.2016 (7) | 0.3951 (7) | 0.092 (3) | |
H55 | 0.5733 | 0.1770 | 0.4274 | 0.110* | |
C56 | 0.6173 (6) | 0.1987 (6) | 0.3190 (7) | 0.083 (3) | |
H56 | 0.5748 | 0.1734 | 0.2982 | 0.099* | |
C51A | 0.7547 (7) | 0.4498 (6) | 0.3686 (7) | 0.074 (3) | |
N52A | 0.7552 (6) | 0.4864 (6) | 0.3006 (6) | 0.099 (3) | |
C53A | 0.6845 (8) | 0.5308 (7) | 0.2878 (6) | 0.093 (3) | |
H53A | 0.6809 | 0.5559 | 0.2397 | 0.112* | |
C54A | 0.6208 (7) | 0.5376 (6) | 0.3451 (7) | 0.079 (3) | |
C55A | 0.6302 (7) | 0.4936 (6) | 0.4146 (7) | 0.093 (3) | |
H55A | 0.5876 | 0.4949 | 0.4547 | 0.112* | |
C56A | 0.6950 (6) | 0.4515 (5) | 0.4252 (5) | 0.065 (2) | |
H56A | 0.6991 | 0.4232 | 0.4719 | 0.078* | |
C57A | 0.5455 (8) | 0.5864 (7) | 0.3334 (9) | 0.100 (4) | |
O51A | 0.5411 (6) | 0.6268 (6) | 0.2756 (6) | 0.131 (3) | |
O52A | 0.4903 (5) | 0.5797 (5) | 0.3953 (5) | 0.115 (3) | |
C58A | 0.4127 (10) | 0.6276 (9) | 0.3867 (10) | 0.167 (7) | |
H58A | 0.3813 | 0.6315 | 0.4363 | 0.251* | |
H58B | 0.3804 | 0.6008 | 0.3529 | 0.251* | |
H58C | 0.4272 | 0.6808 | 0.3653 | 0.251* | |
C61 | 0.9789 (7) | 0.3977 (7) | 0.3810 (6) | 0.088 (3) | |
C62 | 0.9948 (6) | 0.3542 (6) | 0.3135 (6) | 0.079 (3) | |
H62 | 0.9529 | 0.3469 | 0.2828 | 0.095* | |
C63 | 1.0687 (6) | 0.3235 (5) | 0.2932 (5) | 0.068 (2) | |
C64 | 1.1317 (7) | 0.3326 (7) | 0.3419 (7) | 0.097 (3) | |
H64 | 1.1833 | 0.3096 | 0.3301 | 0.116* | |
C65 | 1.1145 (9) | 0.3762 (9) | 0.4072 (8) | 0.111 (4) | |
H65 | 1.1544 | 0.3819 | 0.4404 | 0.134* | |
C66 | 1.0413 (9) | 0.4100 (8) | 0.4227 (8) | 0.113 (4) | |
H66 | 1.0328 | 0.4435 | 0.4641 | 0.136* | |
C61A | 1.0513 (5) | 0.2496 (5) | 0.0946 (6) | 0.060 (2) | |
N62A | 1.0627 (5) | 0.2870 (4) | 0.0282 (5) | 0.068 (2) | |
C63A | 1.0598 (5) | 0.2471 (6) | −0.0363 (6) | 0.071 (3) | |
H63A | 1.0663 | 0.2749 | −0.0841 | 0.085* | |
C64A | 1.0467 (6) | 0.1628 (6) | −0.0317 (7) | 0.076 (3) | |
C65A | 1.0370 (6) | 0.1252 (6) | 0.0367 (8) | 0.083 (3) | |
H65A | 1.0305 | 0.0694 | 0.0396 | 0.099* | |
C66A | 1.0359 (6) | 0.1663 (6) | 0.1065 (6) | 0.075 (3) | |
H66A | 1.0260 | 0.1406 | 0.1552 | 0.090* | |
C67A | 1.0452 (6) | 0.1199 (9) | −0.1070 (10) | 0.096 (4) | |
O61A | 1.0472 (6) | 0.0446 (5) | −0.1001 (5) | 0.140 (4) | |
O62A | 1.0460 (5) | 0.1665 (5) | −0.1666 (5) | 0.099 (3) | |
C68A | 1.0540 (8) | 0.1295 (9) | −0.2406 (8) | 0.129 (5) | |
H68A | 1.0136 | 0.0874 | −0.2397 | 0.193* | |
H68B | 1.1082 | 0.1070 | −0.2506 | 0.193* | |
H68C | 1.0456 | 0.1695 | −0.2804 | 0.193* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.074 (5) | 0.065 (4) | 0.141 (6) | 0.000 (4) | −0.023 (4) | −0.012 (4) |
C1A | 0.066 (7) | 0.077 (8) | 0.093 (8) | −0.015 (6) | −0.019 (6) | −0.015 (6) |
N1 | 0.073 (5) | 0.053 (5) | 0.084 (6) | 0.006 (4) | −0.016 (4) | 0.007 (4) |
O2A | 0.088 (5) | 0.081 (5) | 0.114 (6) | 0.033 (4) | −0.007 (4) | −0.009 (4) |
C2A | 0.069 (7) | 0.063 (7) | 0.106 (9) | 0.002 (6) | −0.013 (6) | −0.013 (6) |
O3A | 0.134 (7) | 0.107 (7) | 0.105 (6) | 0.019 (5) | 0.010 (6) | 0.008 (5) |
C3A | 0.135 (12) | 0.067 (8) | 0.088 (9) | −0.017 (8) | −0.042 (8) | −0.010 (7) |
N2 | 0.072 (6) | 0.069 (6) | 0.101 (6) | 0.009 (5) | −0.001 (5) | −0.011 (5) |
O4A | 0.095 (6) | 0.096 (6) | 0.170 (8) | 0.004 (5) | −0.016 (5) | −0.050 (6) |
C4A | 0.099 (9) | 0.075 (8) | 0.103 (8) | −0.006 (7) | −0.013 (6) | −0.033 (6) |
O5A | 0.090 (5) | 0.063 (5) | 0.125 (6) | −0.011 (4) | 0.000 (4) | 0.003 (4) |
C5A | 0.075 (7) | 0.046 (6) | 0.088 (8) | −0.005 (5) | −0.022 (6) | 0.010 (6) |
N3 | 0.065 (5) | 0.042 (5) | 0.106 (7) | −0.010 (4) | −0.023 (5) | 0.007 (5) |
O6A | 0.079 (5) | 0.064 (5) | 0.172 (8) | 0.038 (4) | −0.014 (5) | 0.010 (4) |
C6A | 0.084 (8) | 0.048 (6) | 0.086 (7) | −0.013 (6) | −0.016 (6) | 0.004 (5) |
C11 | 0.074 (7) | 0.042 (5) | 0.056 (5) | −0.010 (5) | −0.014 (4) | 0.000 (4) |
C12 | 0.071 (7) | 0.038 (5) | 0.081 (6) | −0.003 (5) | −0.026 (5) | 0.011 (4) |
C13 | 0.053 (6) | 0.044 (6) | 0.081 (6) | 0.002 (4) | −0.012 (5) | −0.009 (4) |
C14 | 0.082 (7) | 0.045 (6) | 0.076 (6) | −0.012 (5) | 0.001 (5) | 0.003 (5) |
C15 | 0.093 (8) | 0.037 (5) | 0.104 (8) | −0.015 (6) | −0.019 (6) | 0.008 (5) |
C16 | 0.090 (8) | 0.051 (6) | 0.105 (8) | 0.007 (6) | −0.030 (6) | 0.004 (5) |
C11A | 0.060 (6) | 0.070 (8) | 0.097 (9) | 0.018 (6) | −0.013 (6) | −0.020 (7) |
N12A | 0.077 (6) | 0.064 (5) | 0.091 (7) | −0.006 (4) | 0.003 (5) | −0.008 (5) |
C13A | 0.072 (7) | 0.059 (7) | 0.094 (8) | −0.006 (5) | −0.008 (5) | −0.019 (6) |
C14A | 0.049 (6) | 0.071 (7) | 0.098 (8) | 0.019 (5) | −0.015 (5) | −0.016 (6) |
C15A | 0.073 (7) | 0.071 (7) | 0.110 (10) | 0.010 (5) | −0.008 (7) | 0.004 (8) |
C16A | 0.083 (7) | 0.069 (8) | 0.086 (8) | 0.013 (6) | −0.001 (6) | 0.012 (6) |
C17A | 0.054 (6) | 0.074 (9) | 0.131 (12) | 0.002 (6) | −0.011 (7) | −0.009 (8) |
O11A | 0.109 (7) | 0.109 (7) | 0.143 (8) | 0.003 (5) | −0.025 (6) | −0.025 (6) |
O12A | 0.100 (6) | 0.079 (6) | 0.157 (8) | −0.019 (4) | 0.009 (5) | −0.043 (5) |
C18A | 0.153 (14) | 0.125 (12) | 0.238 (19) | −0.032 (10) | 0.018 (13) | −0.102 (13) |
C21 | 0.068 (7) | 0.047 (5) | 0.091 (7) | 0.001 (5) | −0.009 (6) | −0.016 (5) |
C22 | 0.081 (7) | 0.071 (7) | 0.081 (8) | −0.003 (6) | −0.009 (6) | 0.008 (5) |
C23 | 0.057 (6) | 0.089 (8) | 0.114 (10) | 0.010 (6) | −0.008 (6) | −0.019 (7) |
C24 | 0.096 (9) | 0.106 (9) | 0.084 (8) | 0.018 (7) | −0.024 (7) | −0.001 (7) |
C25 | 0.127 (12) | 0.107 (10) | 0.109 (11) | 0.026 (9) | −0.030 (9) | 0.000 (8) |
C26 | 0.085 (8) | 0.098 (9) | 0.120 (11) | 0.049 (7) | −0.031 (8) | −0.028 (7) |
C21A | 0.100 (10) | 0.081 (8) | 0.108 (10) | 0.014 (7) | −0.008 (8) | −0.018 (7) |
N22A | 0.104 (8) | 0.116 (8) | 0.082 (7) | −0.004 (6) | −0.031 (6) | −0.005 (5) |
C23A | 0.098 (9) | 0.119 (10) | 0.074 (8) | −0.020 (8) | −0.004 (7) | 0.002 (7) |
C24A | 0.087 (9) | 0.093 (9) | 0.099 (10) | −0.006 (7) | −0.014 (8) | −0.009 (7) |
C25A | 0.111 (11) | 0.065 (8) | 0.157 (14) | −0.009 (8) | 0.032 (11) | −0.006 (8) |
C26A | 0.143 (12) | 0.084 (8) | 0.084 (9) | 0.035 (9) | −0.026 (8) | −0.002 (7) |
C27A | 0.103 (12) | 0.097 (11) | 0.131 (14) | 0.009 (9) | 0.011 (10) | 0.017 (9) |
O21A | 0.134 (9) | 0.148 (9) | 0.171 (11) | −0.011 (7) | 0.030 (7) | 0.018 (8) |
O22A | 0.118 (7) | 0.111 (7) | 0.188 (10) | −0.036 (6) | −0.021 (7) | 0.024 (6) |
C28A | 0.23 (2) | 0.21 (2) | 0.24 (2) | −0.175 (19) | −0.068 (17) | 0.080 (16) |
C31 | 0.093 (9) | 0.077 (7) | 0.101 (8) | 0.004 (6) | −0.020 (7) | −0.018 (6) |
C32 | 0.086 (8) | 0.066 (6) | 0.091 (8) | 0.000 (6) | −0.002 (6) | −0.017 (6) |
C33 | 0.071 (7) | 0.073 (7) | 0.100 (8) | −0.003 (6) | −0.013 (7) | 0.005 (6) |
C34 | 0.088 (9) | 0.108 (10) | 0.109 (9) | 0.002 (7) | −0.014 (8) | −0.019 (8) |
C35 | 0.093 (10) | 0.120 (11) | 0.127 (11) | 0.016 (8) | −0.013 (8) | 0.001 (9) |
C36 | 0.085 (9) | 0.113 (10) | 0.121 (10) | 0.012 (7) | −0.009 (8) | −0.033 (8) |
C31A | 0.064 (6) | 0.045 (6) | 0.074 (7) | −0.005 (4) | −0.016 (5) | −0.002 (6) |
N32A | 0.085 (6) | 0.054 (5) | 0.090 (6) | 0.001 (4) | −0.030 (5) | −0.005 (5) |
C33A | 0.075 (7) | 0.074 (8) | 0.093 (8) | 0.011 (5) | −0.015 (6) | −0.001 (6) |
C34A | 0.056 (6) | 0.068 (7) | 0.116 (9) | 0.011 (5) | −0.019 (6) | −0.010 (7) |
C35A | 0.070 (7) | 0.056 (6) | 0.115 (9) | 0.017 (5) | −0.017 (6) | 0.008 (7) |
C36A | 0.089 (8) | 0.078 (8) | 0.112 (9) | 0.009 (6) | −0.013 (7) | −0.013 (7) |
C37A | 0.102 (9) | 0.089 (10) | 0.112 (11) | 0.032 (8) | −0.039 (8) | −0.035 (9) |
O31A | 0.198 (10) | 0.086 (6) | 0.162 (8) | 0.068 (7) | −0.076 (7) | −0.050 (6) |
O32A | 0.075 (5) | 0.105 (6) | 0.131 (7) | −0.003 (4) | −0.005 (5) | −0.028 (6) |
C38A | 0.101 (9) | 0.113 (10) | 0.128 (11) | 0.007 (7) | −0.019 (8) | −0.040 (8) |
O1B | 0.076 (5) | 0.053 (4) | 0.146 (7) | 0.012 (4) | −0.005 (4) | 0.001 (4) |
C1B | 0.071 (7) | 0.047 (6) | 0.094 (7) | 0.013 (5) | −0.027 (5) | −0.015 (5) |
N4 | 0.059 (5) | 0.049 (5) | 0.081 (6) | −0.008 (4) | −0.011 (4) | −0.005 (4) |
O2B | 0.084 (5) | 0.081 (5) | 0.103 (5) | −0.024 (4) | −0.016 (4) | −0.004 (4) |
C2B | 0.080 (7) | 0.065 (7) | 0.079 (8) | 0.007 (6) | −0.003 (6) | −0.001 (6) |
O3B | 0.120 (7) | 0.104 (6) | 0.111 (6) | −0.019 (5) | −0.026 (5) | 0.017 (5) |
C3B | 0.077 (8) | 0.104 (10) | 0.084 (8) | 0.023 (7) | −0.010 (7) | −0.017 (7) |
N5 | 0.057 (5) | 0.082 (6) | 0.096 (6) | −0.007 (5) | −0.017 (4) | −0.024 (5) |
O4B | 0.103 (6) | 0.075 (5) | 0.186 (9) | 0.009 (5) | −0.017 (5) | −0.075 (6) |
C4B | 0.060 (7) | 0.116 (10) | 0.124 (10) | 0.007 (7) | 0.005 (6) | −0.039 (8) |
O5B | 0.075 (5) | 0.082 (5) | 0.112 (6) | 0.017 (4) | −0.016 (4) | −0.010 (4) |
C5B | 0.060 (6) | 0.065 (7) | 0.092 (8) | 0.007 (5) | −0.015 (6) | −0.004 (6) |
N6 | 0.061 (5) | 0.054 (5) | 0.090 (6) | −0.003 (4) | −0.013 (4) | 0.000 (4) |
O6B | 0.084 (5) | 0.064 (5) | 0.135 (6) | −0.021 (4) | −0.018 (4) | −0.001 (4) |
C6B | 0.067 (7) | 0.026 (5) | 0.109 (8) | 0.005 (5) | −0.008 (5) | −0.003 (5) |
C41 | 0.068 (7) | 0.039 (6) | 0.088 (7) | 0.003 (5) | −0.004 (5) | −0.009 (5) |
C42 | 0.060 (6) | 0.047 (5) | 0.076 (6) | 0.004 (5) | 0.002 (5) | −0.001 (4) |
C43 | 0.068 (7) | 0.055 (6) | 0.091 (7) | −0.005 (5) | −0.013 (5) | −0.010 (5) |
C44 | 0.088 (8) | 0.049 (6) | 0.092 (7) | 0.001 (6) | −0.005 (6) | −0.004 (5) |
C45 | 0.102 (9) | 0.051 (6) | 0.105 (8) | −0.016 (6) | 0.000 (7) | −0.015 (5) |
C46 | 0.072 (7) | 0.057 (7) | 0.094 (7) | 0.003 (5) | −0.002 (6) | −0.002 (5) |
C41A | 0.084 (7) | 0.057 (7) | 0.074 (7) | −0.009 (5) | −0.009 (6) | 0.001 (6) |
N42A | 0.053 (5) | 0.069 (6) | 0.100 (7) | 0.000 (4) | −0.005 (5) | −0.030 (6) |
C43A | 0.056 (6) | 0.055 (7) | 0.100 (8) | 0.001 (5) | −0.007 (5) | 0.001 (6) |
C44A | 0.053 (6) | 0.060 (7) | 0.092 (8) | −0.007 (5) | −0.023 (5) | 0.001 (6) |
C45A | 0.077 (7) | 0.055 (6) | 0.115 (10) | −0.013 (5) | −0.016 (7) | −0.006 (7) |
C46A | 0.076 (7) | 0.059 (7) | 0.087 (8) | 0.002 (5) | −0.021 (5) | 0.005 (6) |
C47A | 0.062 (6) | 0.062 (8) | 0.115 (10) | −0.002 (5) | −0.030 (6) | −0.014 (7) |
O41A | 0.114 (7) | 0.105 (7) | 0.135 (8) | 0.007 (5) | −0.028 (6) | −0.028 (6) |
O42A | 0.121 (6) | 0.064 (5) | 0.167 (8) | 0.021 (4) | −0.031 (5) | −0.049 (5) |
C48A | 0.165 (14) | 0.111 (11) | 0.207 (16) | 0.031 (10) | −0.072 (12) | −0.088 (11) |
C51 | 0.068 (7) | 0.048 (6) | 0.101 (8) | −0.006 (5) | −0.014 (6) | −0.002 (5) |
C52 | 0.074 (7) | 0.068 (7) | 0.074 (8) | 0.004 (5) | 0.000 (6) | −0.002 (5) |
C53 | 0.060 (7) | 0.080 (7) | 0.074 (8) | 0.009 (5) | −0.004 (6) | 0.003 (5) |
C54 | 0.079 (8) | 0.100 (8) | 0.084 (8) | 0.014 (6) | −0.009 (7) | −0.009 (6) |
C55 | 0.102 (9) | 0.106 (9) | 0.065 (8) | 0.002 (7) | 0.001 (7) | −0.004 (6) |
C56 | 0.064 (7) | 0.061 (6) | 0.124 (10) | −0.010 (5) | −0.017 (6) | 0.002 (6) |
C51A | 0.079 (8) | 0.059 (6) | 0.083 (8) | −0.012 (5) | −0.008 (7) | −0.004 (6) |
N52A | 0.103 (8) | 0.087 (7) | 0.104 (8) | −0.007 (6) | 0.001 (6) | −0.006 (6) |
C53A | 0.093 (9) | 0.114 (9) | 0.072 (7) | 0.000 (7) | −0.007 (7) | 0.000 (6) |
C54A | 0.092 (8) | 0.059 (6) | 0.088 (8) | 0.001 (6) | −0.016 (7) | 0.004 (6) |
C55A | 0.080 (8) | 0.068 (7) | 0.128 (11) | 0.010 (6) | 0.002 (7) | −0.010 (7) |
C56A | 0.074 (7) | 0.069 (6) | 0.050 (6) | 0.014 (5) | 0.004 (5) | 0.007 (4) |
C57A | 0.099 (10) | 0.081 (9) | 0.117 (11) | −0.014 (7) | −0.007 (9) | 0.005 (8) |
O51A | 0.142 (8) | 0.128 (7) | 0.119 (7) | 0.008 (6) | −0.020 (6) | 0.052 (6) |
O52A | 0.094 (6) | 0.098 (6) | 0.145 (7) | 0.025 (5) | 0.000 (5) | 0.032 (5) |
C58A | 0.134 (13) | 0.121 (12) | 0.227 (18) | 0.046 (10) | 0.039 (12) | 0.046 (11) |
C61 | 0.080 (8) | 0.097 (8) | 0.089 (8) | 0.003 (6) | −0.013 (6) | −0.018 (6) |
C62 | 0.060 (7) | 0.081 (7) | 0.098 (8) | 0.006 (5) | −0.003 (5) | −0.024 (6) |
C63 | 0.076 (7) | 0.054 (6) | 0.073 (6) | 0.003 (5) | −0.008 (6) | −0.009 (5) |
C64 | 0.087 (8) | 0.102 (9) | 0.105 (9) | −0.004 (6) | −0.021 (7) | −0.013 (7) |
C65 | 0.090 (10) | 0.134 (11) | 0.116 (10) | 0.009 (8) | −0.026 (7) | −0.032 (9) |
C66 | 0.094 (10) | 0.117 (10) | 0.135 (11) | 0.000 (8) | −0.020 (9) | −0.049 (8) |
C61A | 0.046 (5) | 0.049 (6) | 0.083 (7) | 0.006 (4) | −0.007 (5) | 0.000 (6) |
N62A | 0.084 (6) | 0.036 (4) | 0.080 (6) | −0.003 (4) | 0.003 (4) | −0.001 (4) |
C63A | 0.060 (6) | 0.057 (7) | 0.095 (8) | −0.002 (5) | −0.003 (5) | −0.014 (6) |
C64A | 0.067 (7) | 0.055 (7) | 0.106 (9) | −0.007 (5) | −0.006 (6) | −0.010 (6) |
C65A | 0.077 (7) | 0.052 (6) | 0.118 (10) | −0.008 (5) | −0.006 (6) | −0.003 (7) |
C66A | 0.065 (6) | 0.063 (7) | 0.095 (8) | 0.006 (5) | 0.000 (5) | 0.003 (6) |
C67A | 0.052 (6) | 0.080 (10) | 0.158 (13) | −0.005 (6) | 0.008 (7) | −0.064 (9) |
O61A | 0.198 (10) | 0.072 (6) | 0.140 (7) | −0.072 (6) | 0.037 (6) | −0.038 (5) |
O62A | 0.106 (6) | 0.091 (6) | 0.106 (6) | 0.025 (5) | −0.030 (5) | −0.014 (5) |
C68A | 0.106 (10) | 0.142 (12) | 0.138 (12) | −0.020 (8) | 0.002 (8) | −0.049 (10) |
Geometric parameters (Å, º) top
O1A—C1A | 1.182 (11) | O1B—C1B | 1.204 (11) |
C1A—C13 | 1.438 (13) | C1B—N4 | 1.447 (11) |
C1A—N1 | 1.445 (13) | C1B—C43 | 1.453 (14) |
N1—C11A | 1.395 (12) | N4—C2B | 1.388 (12) |
N1—C2A | 1.413 (13) | N4—C41A | 1.393 (12) |
O2A—C2A | 1.235 (11) | O2B—C2B | 1.212 (11) |
C2A—C21 | 1.475 (14) | C2B—C51 | 1.500 (14) |
O3A—C3A | 1.230 (14) | O3B—C3B | 1.197 (12) |
C3A—N2 | 1.338 (13) | C3B—C53 | 1.408 (15) |
C3A—C23 | 1.526 (16) | C3B—N5 | 1.461 (15) |
N2—C4A | 1.394 (14) | N5—C51A | 1.460 (13) |
N2—C21A | 1.430 (15) | N5—C4B | 1.465 (14) |
O4A—C4A | 1.229 (12) | O4B—C4B | 1.124 (12) |
C4A—C31 | 1.485 (15) | C4B—C61 | 1.553 (16) |
O5A—C5A | 1.198 (11) | O5B—C5B | 1.245 (11) |
C5A—N3 | 1.396 (12) | C5B—N6 | 1.344 (12) |
C5A—C33 | 1.422 (14) | C5B—C63 | 1.465 (13) |
N3—C31A | 1.407 (12) | N6—C6B | 1.447 (11) |
N3—C6A | 1.492 (11) | N6—C61A | 1.466 (12) |
O6A—C6A | 1.205 (11) | O6B—C6B | 1.197 (10) |
C6A—C11 | 1.481 (13) | C6B—C41 | 1.481 (13) |
C11—C12 | 1.367 (12) | C41—C46 | 1.374 (12) |
C11—C16 | 1.423 (12) | C41—C42 | 1.394 (12) |
C12—C13 | 1.389 (12) | C42—C43 | 1.385 (12) |
C12—H12 | 0.9300 | C42—H42 | 0.9300 |
C13—C14 | 1.408 (12) | C43—C44 | 1.425 (13) |
C14—C15 | 1.396 (13) | C44—C45 | 1.407 (14) |
C14—H14 | 0.9300 | C44—H44 | 0.9300 |
C15—C16 | 1.365 (14) | C45—C46 | 1.386 (14) |
C15—H15 | 0.9300 | C45—H45 | 0.9300 |
C16—H16 | 0.9300 | C46—H46 | 0.9300 |
C11A—N12A | 1.298 (13) | C41A—N42A | 1.304 (12) |
C11A—C16A | 1.414 (14) | C41A—C46A | 1.433 (13) |
N12A—C13A | 1.319 (12) | N42A—C43A | 1.266 (12) |
C13A—C14A | 1.400 (13) | C43A—C44A | 1.426 (13) |
C13A—H13A | 0.9300 | C43A—H43A | 0.9300 |
C14A—C15A | 1.378 (14) | C44A—C45A | 1.347 (13) |
C14A—C17A | 1.522 (16) | C44A—C47A | 1.448 (15) |
C15A—C16A | 1.301 (14) | C45A—C46A | 1.346 (13) |
C15A—H15A | 0.9300 | C45A—H45A | 0.9300 |
C16A—H16A | 0.9300 | C46A—H46A | 0.9300 |
C17A—O11A | 1.191 (13) | C47A—O41A | 1.221 (13) |
C17A—O12A | 1.296 (13) | C47A—O42A | 1.282 (12) |
O12A—C18A | 1.515 (16) | O42A—C48A | 1.498 (14) |
C18A—H18A | 0.9600 | C48A—H48A | 0.9600 |
C18A—H18B | 0.9600 | C48A—H48B | 0.9600 |
C18A—H18C | 0.9600 | C48A—H48C | 0.9600 |
C21—C22 | 1.370 (13) | C51—C52 | 1.354 (13) |
C21—C26 | 1.419 (14) | C51—C56 | 1.451 (14) |
C22—C23 | 1.406 (14) | C52—C53 | 1.342 (13) |
C22—H22 | 0.9300 | C52—H52 | 0.9300 |
C23—C24 | 1.377 (15) | C53—C54 | 1.424 (14) |
C24—C25 | 1.344 (16) | C54—C55 | 1.402 (15) |
C24—H24 | 0.9300 | C54—H54 | 0.9300 |
C25—C26 | 1.329 (16) | C55—C56 | 1.330 (14) |
C25—H25 | 0.9300 | C55—H55 | 0.9300 |
C26—H26 | 0.9300 | C56—H56 | 0.9300 |
C21A—N22A | 1.303 (14) | C51A—C56A | 1.308 (13) |
C21A—C26A | 1.448 (17) | C51A—N52A | 1.309 (13) |
N22A—C23A | 1.302 (14) | N52A—C53A | 1.401 (14) |
C23A—C24A | 1.410 (16) | C53A—C54A | 1.367 (15) |
C23A—H23A | 0.9300 | C53A—H53A | 0.9300 |
C24A—C25A | 1.314 (18) | C54A—C55A | 1.409 (15) |
C24A—C27A | 1.481 (19) | C54A—C57A | 1.500 (16) |
C25A—C26A | 1.357 (18) | C55A—C56A | 1.294 (13) |
C25A—H25A | 0.9300 | C55A—H55A | 0.9300 |
C26A—H26A | 0.9300 | C56A—H56A | 0.9300 |
C27A—O21A | 1.160 (15) | C57A—O51A | 1.195 (14) |
C27A—O22A | 1.344 (17) | C57A—O52A | 1.325 (14) |
O22A—C28A | 1.423 (16) | O52A—C58A | 1.513 (16) |
C28A—H28A | 0.9600 | C58A—H58A | 0.9600 |
C28A—H28B | 0.9600 | C58A—H58B | 0.9600 |
C28A—H28C | 0.9600 | C58A—H58C | 0.9600 |
C31—C32 | 1.381 (14) | C61—C66 | 1.342 (15) |
C31—C36 | 1.403 (16) | C61—C62 | 1.411 (14) |
C32—C33 | 1.431 (14) | C62—C63 | 1.324 (13) |
C32—H32 | 0.9300 | C62—H62 | 0.9300 |
C33—C34 | 1.395 (15) | C63—C64 | 1.423 (14) |
C34—C35 | 1.336 (16) | C64—C65 | 1.381 (16) |
C34—H34 | 0.9300 | C64—H64 | 0.9300 |
C35—C36 | 1.369 (17) | C65—C66 | 1.324 (16) |
C35—H35 | 0.9300 | C65—H65 | 0.9300 |
C36—H36 | 0.9300 | C66—H66 | 0.9300 |
C31A—N32A | 1.291 (11) | C61A—N62A | 1.283 (11) |
C31A—C36A | 1.377 (13) | C61A—C66A | 1.406 (13) |
N32A—C33A | 1.383 (12) | N62A—C63A | 1.341 (11) |
C33A—C34A | 1.372 (13) | C63A—C64A | 1.411 (13) |
C33A—H33A | 0.9300 | C63A—H63A | 0.9300 |
C34A—C35A | 1.392 (14) | C64A—C65A | 1.314 (14) |
C34A—C37A | 1.504 (16) | C64A—C67A | 1.527 (16) |
C35A—C36A | 1.413 (15) | C65A—C66A | 1.425 (14) |
C35A—H35A | 0.9300 | C65A—H65A | 0.9300 |
C36A—H36A | 0.9300 | C66A—H66A | 0.9300 |
C37A—O31A | 1.201 (15) | C67A—O61A | 1.249 (15) |
C37A—O32A | 1.279 (15) | C67A—O62A | 1.265 (16) |
O32A—C38A | 1.433 (13) | O62A—C68A | 1.449 (14) |
C38A—H38A | 0.9600 | C68A—H68A | 0.9600 |
C38A—H38B | 0.9600 | C68A—H68B | 0.9600 |
C38A—H38C | 0.9600 | C68A—H68C | 0.9600 |
| | | |
O1A—C1A—C13 | 121.2 (10) | O1B—C1B—N4 | 118.1 (9) |
O1A—C1A—N1 | 120.9 (10) | O1B—C1B—C43 | 123.9 (8) |
C13—C1A—N1 | 117.8 (9) | N4—C1B—C43 | 118.0 (9) |
C11A—N1—C2A | 120.5 (8) | C2B—N4—C41A | 120.3 (8) |
C11A—N1—C1A | 116.8 (8) | C2B—N4—C1B | 118.6 (8) |
C2A—N1—C1A | 116.6 (8) | C41A—N4—C1B | 116.2 (8) |
O2A—C2A—N1 | 117.7 (9) | O2B—C2B—N4 | 120.3 (9) |
O2A—C2A—C21 | 121.4 (10) | O2B—C2B—C51 | 121.9 (9) |
N1—C2A—C21 | 120.2 (9) | N4—C2B—C51 | 117.5 (10) |
O3A—C3A—N2 | 123.0 (13) | O3B—C3B—C53 | 126.3 (12) |
O3A—C3A—C23 | 119.8 (11) | O3B—C3B—N5 | 117.6 (11) |
N2—C3A—C23 | 117.2 (12) | C53—C3B—N5 | 115.6 (11) |
C3A—N2—C4A | 119.0 (11) | C51A—N5—C3B | 115.8 (8) |
C3A—N2—C21A | 119.0 (10) | C51A—N5—C4B | 113.4 (9) |
C4A—N2—C21A | 119.2 (9) | C3B—N5—C4B | 126.4 (10) |
O4A—C4A—N2 | 117.4 (10) | O4B—C4B—N5 | 121.7 (10) |
O4A—C4A—C31 | 120.4 (11) | O4B—C4B—C61 | 126.9 (11) |
N2—C4A—C31 | 121.8 (10) | N5—C4B—C61 | 111.2 (11) |
O5A—C5A—N3 | 120.3 (9) | O5B—C5B—N6 | 119.7 (9) |
O5A—C5A—C33 | 121.9 (10) | O5B—C5B—C63 | 123.5 (10) |
N3—C5A—C33 | 117.8 (9) | N6—C5B—C63 | 116.8 (9) |
C5A—N3—C31A | 124.5 (8) | C5B—N6—C6B | 121.2 (8) |
C5A—N3—C6A | 118.4 (8) | C5B—N6—C61A | 124.7 (8) |
C31A—N3—C6A | 114.6 (8) | C6B—N6—C61A | 111.8 (8) |
O6A—C6A—C11 | 126.7 (9) | O6B—C6B—N6 | 119.0 (9) |
O6A—C6A—N3 | 119.7 (9) | O6B—C6B—C41 | 122.7 (8) |
C11—C6A—N3 | 113.5 (9) | N6—C6B—C41 | 118.0 (8) |
C12—C11—C16 | 118.1 (9) | C46—C41—C42 | 120.2 (9) |
C12—C11—C6A | 126.0 (8) | C46—C41—C6B | 117.7 (9) |
C16—C11—C6A | 115.8 (9) | C42—C41—C6B | 121.9 (8) |
C11—C12—C13 | 121.9 (8) | C43—C42—C41 | 119.9 (8) |
C11—C12—H12 | 119.0 | C43—C42—H42 | 120.0 |
C13—C12—H12 | 119.0 | C41—C42—H42 | 120.0 |
C12—C13—C14 | 119.9 (8) | C42—C43—C44 | 120.8 (9) |
C12—C13—C1A | 120.8 (8) | C42—C43—C1B | 121.0 (9) |
C14—C13—C1A | 118.5 (9) | C44—C43—C1B | 117.5 (9) |
C15—C14—C13 | 118.0 (9) | C45—C44—C43 | 117.4 (10) |
C15—C14—H14 | 121.0 | C45—C44—H44 | 121.3 |
C13—C14—H14 | 121.0 | C43—C44—H44 | 121.3 |
C16—C15—C14 | 121.4 (9) | C46—C45—C44 | 121.0 (10) |
C16—C15—H15 | 119.3 | C46—C45—H45 | 119.5 |
C14—C15—H15 | 119.3 | C44—C45—H45 | 119.5 |
C15—C16—C11 | 120.2 (9) | C41—C46—C45 | 120.6 (10) |
C15—C16—H16 | 119.9 | C41—C46—H46 | 119.7 |
C11—C16—H16 | 119.9 | C45—C46—H46 | 119.7 |
N12A—C11A—N1 | 120.8 (10) | N42A—C41A—N4 | 120.9 (9) |
N12A—C11A—C16A | 121.0 (10) | N42A—C41A—C46A | 120.5 (9) |
N1—C11A—C16A | 118.2 (11) | N4—C41A—C46A | 118.3 (10) |
C11A—N12A—C13A | 120.7 (9) | C43A—N42A—C41A | 119.9 (9) |
N12A—C13A—C14A | 119.4 (10) | N42A—C43A—C44A | 124.8 (10) |
N12A—C13A—H13A | 120.3 | N42A—C43A—H43A | 117.6 |
C14A—C13A—H13A | 120.3 | C44A—C43A—H43A | 117.6 |
C15A—C14A—C13A | 119.6 (10) | C45A—C44A—C43A | 114.4 (10) |
C15A—C14A—C17A | 123.6 (11) | C45A—C44A—C47A | 123.5 (10) |
C13A—C14A—C17A | 116.6 (11) | C43A—C44A—C47A | 122.1 (10) |
C16A—C15A—C14A | 119.0 (11) | C46A—C45A—C44A | 122.5 (10) |
C16A—C15A—H15A | 120.5 | C46A—C45A—H45A | 118.7 |
C14A—C15A—H15A | 120.5 | C44A—C45A—H45A | 118.7 |
C15A—C16A—C11A | 119.7 (11) | C45A—C46A—C41A | 117.4 (10) |
C15A—C16A—H16A | 120.1 | C45A—C46A—H46A | 121.3 |
C11A—C16A—H16A | 120.1 | C41A—C46A—H46A | 121.3 |
O11A—C17A—O12A | 123.6 (13) | O41A—C47A—O42A | 122.5 (12) |
O11A—C17A—C14A | 122.8 (12) | O41A—C47A—C44A | 124.1 (11) |
O12A—C17A—C14A | 113.4 (12) | O42A—C47A—C44A | 113.1 (12) |
C17A—O12A—C18A | 115.4 (11) | C47A—O42A—C48A | 117.3 (11) |
O12A—C18A—H18A | 109.5 | O42A—C48A—H48A | 109.5 |
O12A—C18A—H18B | 109.5 | O42A—C48A—H48B | 109.5 |
H18A—C18A—H18B | 109.5 | H48A—C48A—H48B | 109.5 |
O12A—C18A—H18C | 109.5 | O42A—C48A—H48C | 109.5 |
H18A—C18A—H18C | 109.5 | H48A—C48A—H48C | 109.5 |
H18B—C18A—H18C | 109.5 | H48B—C48A—H48C | 109.5 |
C22—C21—C26 | 121.1 (10) | C52—C51—C56 | 118.5 (10) |
C22—C21—C2A | 120.1 (10) | C52—C51—C2B | 124.9 (9) |
C26—C21—C2A | 118.4 (9) | C56—C51—C2B | 116.1 (9) |
C21—C22—C23 | 117.3 (9) | C53—C52—C51 | 123.6 (10) |
C21—C22—H22 | 121.4 | C53—C52—H52 | 118.2 |
C23—C22—H22 | 121.4 | C51—C52—H52 | 118.2 |
C24—C23—C22 | 119.1 (10) | C52—C53—C3B | 122.1 (10) |
C24—C23—C3A | 124.8 (11) | C52—C53—C54 | 117.9 (10) |
C22—C23—C3A | 115.9 (10) | C3B—C53—C54 | 120.0 (10) |
C25—C24—C23 | 122.7 (11) | C55—C54—C53 | 119.8 (10) |
C25—C24—H24 | 118.7 | C55—C54—H54 | 120.1 |
C23—C24—H24 | 118.7 | C53—C54—H54 | 120.1 |
C26—C25—C24 | 119.6 (12) | C56—C55—C54 | 120.9 (11) |
C26—C25—H25 | 120.2 | C56—C55—H55 | 119.5 |
C24—C25—H25 | 120.2 | C54—C55—H55 | 119.5 |
C25—C26—C21 | 120.0 (10) | C55—C56—C51 | 119.3 (10) |
C25—C26—H26 | 120.0 | C55—C56—H56 | 120.4 |
C21—C26—H26 | 120.0 | C51—C56—H56 | 120.4 |
N22A—C21A—N2 | 117.0 (12) | C56A—C51A—N52A | 126.0 (11) |
N22A—C21A—C26A | 122.0 (13) | C56A—C51A—N5 | 116.7 (10) |
N2—C21A—C26A | 121.0 (13) | N52A—C51A—N5 | 117.3 (10) |
C23A—N22A—C21A | 117.1 (11) | C51A—N52A—C53A | 116.3 (10) |
N22A—C23A—C24A | 124.9 (12) | C54A—C53A—N52A | 121.0 (11) |
N22A—C23A—H23A | 117.6 | C54A—C53A—H53A | 119.5 |
C24A—C23A—H23A | 117.6 | N52A—C53A—H53A | 119.5 |
C25A—C24A—C23A | 117.4 (13) | C53A—C54A—C55A | 115.2 (11) |
C25A—C24A—C27A | 117.2 (14) | C53A—C54A—C57A | 121.9 (12) |
C23A—C24A—C27A | 125.3 (14) | C55A—C54A—C57A | 122.8 (11) |
C24A—C25A—C26A | 121.1 (14) | C56A—C55A—C54A | 123.2 (11) |
C24A—C25A—H25A | 119.4 | C56A—C55A—H55A | 118.4 |
C26A—C25A—H25A | 119.4 | C54A—C55A—H55A | 118.4 |
C25A—C26A—C21A | 117.2 (13) | C55A—C56A—C51A | 118.2 (10) |
C25A—C26A—H26A | 121.4 | C55A—C56A—H56A | 120.9 |
C21A—C26A—H26A | 121.4 | C51A—C56A—H56A | 120.9 |
O21A—C27A—O22A | 126.7 (16) | O51A—C57A—O52A | 127.7 (13) |
O21A—C27A—C24A | 124.6 (17) | O51A—C57A—C54A | 121.4 (13) |
O22A—C27A—C24A | 108.6 (14) | O52A—C57A—C54A | 110.8 (12) |
C27A—O22A—C28A | 115.7 (13) | C57A—O52A—C58A | 113.1 (10) |
O22A—C28A—H28A | 109.5 | O52A—C58A—H58A | 109.5 |
O22A—C28A—H28B | 109.5 | O52A—C58A—H58B | 109.5 |
H28A—C28A—H28B | 109.5 | H58A—C58A—H58B | 109.5 |
O22A—C28A—H28C | 109.5 | O52A—C58A—H58C | 109.5 |
H28A—C28A—H28C | 109.5 | H58A—C58A—H58C | 109.5 |
H28B—C28A—H28C | 109.5 | H58B—C58A—H58C | 109.5 |
C32—C31—C36 | 119.2 (11) | C66—C61—C62 | 118.3 (10) |
C32—C31—C4A | 119.6 (10) | C66—C61—C4B | 120.2 (11) |
C36—C31—C4A | 121.2 (11) | C62—C61—C4B | 119.6 (10) |
C31—C32—C33 | 122.0 (10) | C63—C62—C61 | 121.0 (10) |
C31—C32—H32 | 119.0 | C63—C62—H62 | 119.5 |
C33—C32—H32 | 119.0 | C61—C62—H62 | 119.5 |
C34—C33—C5A | 122.6 (11) | C62—C63—C64 | 119.1 (10) |
C34—C33—C32 | 115.2 (11) | C62—C63—C5B | 123.0 (10) |
C5A—C33—C32 | 121.9 (10) | C64—C63—C5B | 117.6 (10) |
C35—C34—C33 | 121.7 (12) | C65—C64—C63 | 118.5 (11) |
C35—C34—H34 | 119.2 | C65—C64—H64 | 120.7 |
C33—C34—H34 | 119.2 | C63—C64—H64 | 120.7 |
C34—C35—C36 | 123.2 (13) | C66—C65—C64 | 120.2 (12) |
C34—C35—H35 | 118.4 | C66—C65—H65 | 119.9 |
C36—C35—H35 | 118.4 | C64—C65—H65 | 119.9 |
C35—C36—C31 | 117.9 (12) | C65—C66—C61 | 122.5 (12) |
C35—C36—H36 | 121.0 | C65—C66—H66 | 118.7 |
C31—C36—H36 | 121.0 | C61—C66—H66 | 118.7 |
N32A—C31A—C36A | 125.1 (10) | N62A—C61A—C66A | 124.7 (9) |
N32A—C31A—N3 | 115.0 (8) | N62A—C61A—N6 | 116.0 (8) |
C36A—C31A—N3 | 119.9 (10) | C66A—C61A—N6 | 119.3 (9) |
C31A—N32A—C33A | 117.3 (9) | C61A—N62A—C63A | 120.5 (8) |
C34A—C33A—N32A | 123.2 (10) | N62A—C63A—C64A | 119.9 (10) |
C34A—C33A—H33A | 118.4 | N62A—C63A—H63A | 120.0 |
N32A—C33A—H33A | 118.4 | C64A—C63A—H63A | 120.0 |
C33A—C34A—C35A | 117.5 (10) | C65A—C64A—C63A | 118.7 (10) |
C33A—C34A—C37A | 121.2 (12) | C65A—C64A—C67A | 123.4 (11) |
C35A—C34A—C37A | 121.3 (11) | C63A—C64A—C67A | 117.9 (12) |
C34A—C35A—C36A | 119.4 (10) | C64A—C65A—C66A | 122.8 (10) |
C34A—C35A—H35A | 120.3 | C64A—C65A—H65A | 118.6 |
C36A—C35A—H35A | 120.3 | C66A—C65A—H65A | 118.6 |
C31A—C36A—C35A | 117.3 (11) | C61A—C66A—C65A | 113.3 (9) |
C31A—C36A—H36A | 121.3 | C61A—C66A—H66A | 123.4 |
C35A—C36A—H36A | 121.3 | C65A—C66A—H66A | 123.4 |
O31A—C37A—O32A | 126.6 (12) | O61A—C67A—O62A | 130.4 (12) |
O31A—C37A—C34A | 119.8 (15) | O61A—C67A—C64A | 114.7 (15) |
O32A—C37A—C34A | 113.6 (13) | O62A—C67A—C64A | 114.8 (11) |
C37A—O32A—C38A | 115.3 (10) | C67A—O62A—C68A | 117.3 (10) |
O32A—C38A—H38A | 109.5 | O62A—C68A—H68A | 109.5 |
O32A—C38A—H38B | 109.5 | O62A—C68A—H68B | 109.5 |
H38A—C38A—H38B | 109.5 | H68A—C68A—H68B | 109.5 |
O32A—C38A—H38C | 109.5 | O62A—C68A—H68C | 109.5 |
H38A—C38A—H38C | 109.5 | H68A—C68A—H68C | 109.5 |
H38B—C38A—H38C | 109.5 | H68B—C68A—H68C | 109.5 |
| | | |
O1A—C1A—N1—C11A | 127.5 (10) | O1B—C1B—N4—C2B | −26.1 (13) |
C13—C1A—N1—C11A | −54.9 (12) | C43—C1B—N4—C2B | 152.4 (9) |
O1A—C1A—N1—C2A | −25.2 (14) | O1B—C1B—N4—C41A | 129.3 (10) |
C13—C1A—N1—C2A | 152.3 (9) | C43—C1B—N4—C41A | −52.2 (11) |
C11A—N1—C2A—O2A | −14.3 (14) | C41A—N4—C2B—O2B | −18.0 (14) |
C1A—N1—C2A—O2A | 137.4 (9) | C1B—N4—C2B—O2B | 136.3 (9) |
C11A—N1—C2A—C21 | 155.7 (9) | C41A—N4—C2B—C51 | 155.4 (9) |
C1A—N1—C2A—C21 | −52.6 (12) | C1B—N4—C2B—C51 | −50.2 (11) |
O3A—C3A—N2—C4A | 17.4 (16) | O3B—C3B—N5—C51A | −148.9 (10) |
C23—C3A—N2—C4A | −164.8 (9) | C53—C3B—N5—C51A | 37.7 (12) |
O3A—C3A—N2—C21A | −143.5 (12) | O3B—C3B—N5—C4B | 6.0 (15) |
C23—C3A—N2—C21A | 34.3 (14) | C53—C3B—N5—C4B | −167.4 (9) |
C3A—N2—C4A—O4A | −143.1 (11) | C51A—N5—C4B—O4B | 22.6 (17) |
C21A—N2—C4A—O4A | 17.8 (16) | C3B—N5—C4B—O4B | −132.8 (13) |
C3A—N2—C4A—C31 | 43.9 (15) | C51A—N5—C4B—C61 | −160.9 (9) |
C21A—N2—C4A—C31 | −155.3 (11) | C3B—N5—C4B—C61 | 43.7 (14) |
O5A—C5A—N3—C31A | 11.6 (14) | O5B—C5B—N6—C6B | −148.1 (9) |
C33—C5A—N3—C31A | −169.3 (8) | C63—C5B—N6—C6B | 32.7 (12) |
O5A—C5A—N3—C6A | −149.3 (9) | O5B—C5B—N6—C61A | 13.7 (14) |
C33—C5A—N3—C6A | 29.8 (12) | C63—C5B—N6—C61A | −165.5 (8) |
C5A—N3—C6A—O6A | 44.0 (13) | C5B—N6—C6B—O6B | 41.0 (13) |
C31A—N3—C6A—O6A | −118.7 (10) | C61A—N6—C6B—O6B | −122.9 (9) |
C5A—N3—C6A—C11 | −132.1 (8) | C5B—N6—C6B—C41 | −132.4 (9) |
C31A—N3—C6A—C11 | 65.2 (10) | C61A—N6—C6B—C41 | 63.6 (10) |
O6A—C6A—C11—C12 | −161.0 (10) | O6B—C6B—C41—C46 | 16.7 (14) |
N3—C6A—C11—C12 | 14.8 (12) | N6—C6B—C41—C46 | −170.1 (8) |
O6A—C6A—C11—C16 | 15.1 (14) | O6B—C6B—C41—C42 | −159.0 (9) |
N3—C6A—C11—C16 | −169.2 (8) | N6—C6B—C41—C42 | 14.2 (13) |
C16—C11—C12—C13 | −3.8 (13) | C46—C41—C42—C43 | −2.1 (13) |
C6A—C11—C12—C13 | 172.1 (8) | C6B—C41—C42—C43 | 173.5 (8) |
C11—C12—C13—C14 | 3.7 (13) | C41—C42—C43—C44 | 2.9 (13) |
C11—C12—C13—C1A | −165.9 (8) | C41—C42—C43—C1B | −167.3 (8) |
O1A—C1A—C13—C12 | 141.0 (10) | O1B—C1B—C43—C42 | 140.4 (10) |
N1—C1A—C13—C12 | −36.5 (13) | N4—C1B—C43—C42 | −38.0 (13) |
O1A—C1A—C13—C14 | −28.7 (14) | O1B—C1B—C43—C44 | −30.2 (15) |
N1—C1A—C13—C14 | 153.8 (8) | N4—C1B—C43—C44 | 151.4 (8) |
C12—C13—C14—C15 | 2.1 (13) | C42—C43—C44—C45 | −1.0 (14) |
C1A—C13—C14—C15 | 171.9 (9) | C1B—C43—C44—C45 | 169.6 (9) |
C13—C14—C15—C16 | −7.8 (14) | C43—C44—C45—C46 | −1.8 (14) |
C14—C15—C16—C11 | 7.7 (15) | C42—C41—C46—C45 | −0.6 (14) |
C12—C11—C16—C15 | −1.8 (13) | C6B—C41—C46—C45 | −176.4 (9) |
C6A—C11—C16—C15 | −178.2 (9) | C44—C45—C46—C41 | 2.6 (15) |
C2A—N1—C11A—N12A | 123.7 (10) | C2B—N4—C41A—N42A | 121.3 (10) |
C1A—N1—C11A—N12A | −27.9 (12) | C1B—N4—C41A—N42A | −33.6 (12) |
C2A—N1—C11A—C16A | −55.0 (12) | C2B—N4—C41A—C46A | −52.9 (12) |
C1A—N1—C11A—C16A | 153.3 (9) | C1B—N4—C41A—C46A | 152.2 (8) |
N1—C11A—N12A—C13A | −175.0 (8) | N4—C41A—N42A—C43A | −172.3 (8) |
C16A—C11A—N12A—C13A | 3.7 (14) | C46A—C41A—N42A—C43A | 1.7 (14) |
C11A—N12A—C13A—C14A | 2.7 (14) | C41A—N42A—C43A—C44A | 4.5 (14) |
N12A—C13A—C14A—C15A | −5.0 (13) | N42A—C43A—C44A—C45A | −6.8 (13) |
N12A—C13A—C14A—C17A | 169.2 (8) | N42A—C43A—C44A—C47A | 172.6 (9) |
C13A—C14A—C15A—C16A | 0.7 (14) | C43A—C44A—C45A—C46A | 2.9 (13) |
C17A—C14A—C15A—C16A | −173.1 (9) | C47A—C44A—C45A—C46A | −176.6 (9) |
C14A—C15A—C16A—C11A | 5.5 (15) | C44A—C45A—C46A—C41A | 2.5 (14) |
N12A—C11A—C16A—C15A | −8.0 (15) | N42A—C41A—C46A—C45A | −5.2 (14) |
N1—C11A—C16A—C15A | 170.7 (9) | N4—C41A—C46A—C45A | 169.0 (9) |
C15A—C14A—C17A—O11A | −164.0 (11) | C45A—C44A—C47A—O41A | −165.6 (11) |
C13A—C14A—C17A—O11A | 22.0 (15) | C43A—C44A—C47A—O41A | 15.0 (15) |
C15A—C14A—C17A—O12A | 11.6 (13) | C45A—C44A—C47A—O42A | 20.6 (13) |
C13A—C14A—C17A—O12A | −162.4 (9) | C43A—C44A—C47A—O42A | −158.8 (9) |
O11A—C17A—O12A—C18A | −8.5 (16) | O41A—C47A—O42A—C48A | −0.3 (15) |
C14A—C17A—O12A—C18A | 175.9 (9) | C44A—C47A—O42A—C48A | 173.6 (9) |
O2A—C2A—C21—C22 | 156.2 (9) | O2B—C2B—C51—C52 | 154.6 (10) |
N1—C2A—C21—C22 | −13.4 (13) | N4—C2B—C51—C52 | −18.8 (13) |
O2A—C2A—C21—C26 | −16.6 (14) | O2B—C2B—C51—C56 | −17.2 (13) |
N1—C2A—C21—C26 | 173.8 (9) | N4—C2B—C51—C56 | 169.4 (8) |
C26—C21—C22—C23 | 0.7 (14) | C56—C51—C52—C53 | 3.3 (14) |
C2A—C21—C22—C23 | −171.9 (9) | C2B—C51—C52—C53 | −168.3 (9) |
C21—C22—C23—C24 | 2.1 (14) | C51—C52—C53—C3B | 176.6 (10) |
C21—C22—C23—C3A | 178.1 (9) | C51—C52—C53—C54 | −1.9 (14) |
O3A—C3A—C23—C24 | 50.7 (16) | O3B—C3B—C53—C52 | −118.5 (13) |
N2—C3A—C23—C24 | −127.2 (12) | N5—C3B—C53—C52 | 54.3 (13) |
O3A—C3A—C23—C22 | −125.1 (12) | O3B—C3B—C53—C54 | 60.1 (15) |
N2—C3A—C23—C22 | 57.0 (13) | N5—C3B—C53—C54 | −127.2 (10) |
C22—C23—C24—C25 | −5.7 (18) | C52—C53—C54—C55 | 0.2 (14) |
C3A—C23—C24—C25 | 178.6 (12) | C3B—C53—C54—C55 | −178.4 (10) |
C23—C24—C25—C26 | 6 (2) | C53—C54—C55—C56 | −0.1 (16) |
C24—C25—C26—C21 | −3.2 (19) | C54—C55—C56—C51 | 1.5 (15) |
C22—C21—C26—C25 | −0.2 (17) | C52—C51—C56—C55 | −3.1 (14) |
C2A—C21—C26—C25 | 172.6 (11) | C2B—C51—C56—C55 | 169.3 (9) |
C3A—N2—C21A—N22A | 49.2 (14) | C3B—N5—C51A—C56A | 52.1 (12) |
C4A—N2—C21A—N22A | −111.7 (12) | C4B—N5—C51A—C56A | −106.0 (11) |
C3A—N2—C21A—C26A | −128.9 (11) | C3B—N5—C51A—N52A | −126.3 (10) |
C4A—N2—C21A—C26A | 70.2 (13) | C4B—N5—C51A—N52A | 75.6 (11) |
N2—C21A—N22A—C23A | 178.0 (10) | C56A—C51A—N52A—C53A | −0.6 (15) |
C26A—C21A—N22A—C23A | −3.9 (16) | N5—C51A—N52A—C53A | 177.6 (8) |
C21A—N22A—C23A—C24A | 5.4 (18) | C51A—N52A—C53A—C54A | 2.8 (16) |
N22A—C23A—C24A—C25A | −4.3 (19) | N52A—C53A—C54A—C55A | −3.5 (15) |
N22A—C23A—C24A—C27A | 179.3 (12) | N52A—C53A—C54A—C57A | 178.5 (10) |
C23A—C24A—C25A—C26A | 1.5 (18) | C53A—C54A—C55A—C56A | 2.2 (16) |
C27A—C24A—C25A—C26A | 178.1 (11) | C57A—C54A—C55A—C56A | −179.9 (10) |
C24A—C25A—C26A—C21A | −0.2 (17) | C54A—C55A—C56A—C51A | −0.1 (16) |
N22A—C21A—C26A—C25A | 1.5 (16) | N52A—C51A—C56A—C55A | −0.7 (16) |
N2—C21A—C26A—C25A | 179.5 (10) | N5—C51A—C56A—C55A | −178.9 (9) |
C25A—C24A—C27A—O21A | −4 (2) | C53A—C54A—C57A—O51A | −6.5 (18) |
C23A—C24A—C27A—O21A | 172.5 (14) | C55A—C54A—C57A—O51A | 175.7 (11) |
C25A—C24A—C27A—O22A | 173.0 (11) | C53A—C54A—C57A—O52A | 175.9 (10) |
C23A—C24A—C27A—O22A | −10.6 (17) | C55A—C54A—C57A—O52A | −1.9 (15) |
O21A—C27A—O22A—C28A | −9 (2) | O51A—C57A—O52A—C58A | 2.7 (19) |
C24A—C27A—O22A—C28A | 174.7 (15) | C54A—C57A—O52A—C58A | −179.9 (11) |
O4A—C4A—C31—C32 | −134.2 (12) | O4B—C4B—C61—C66 | 30 (2) |
N2—C4A—C31—C32 | 38.7 (16) | N5—C4B—C61—C66 | −146.4 (11) |
O4A—C4A—C31—C36 | 43.4 (17) | O4B—C4B—C61—C62 | −134.3 (14) |
N2—C4A—C31—C36 | −143.8 (12) | N5—C4B—C61—C62 | 49.5 (14) |
C36—C31—C32—C33 | −1.2 (17) | C66—C61—C62—C63 | 2.5 (17) |
C4A—C31—C32—C33 | 176.4 (10) | C4B—C61—C62—C63 | 166.9 (10) |
O5A—C5A—C33—C34 | 35.8 (15) | C61—C62—C63—C64 | 2.1 (15) |
N3—C5A—C33—C34 | −143.2 (10) | C61—C62—C63—C5B | 176.3 (10) |
O5A—C5A—C33—C32 | −137.4 (10) | O5B—C5B—C63—C62 | −136.1 (11) |
N3—C5A—C33—C32 | 43.6 (13) | N6—C5B—C63—C62 | 43.1 (13) |
C31—C32—C33—C34 | 6.8 (15) | O5B—C5B—C63—C64 | 38.2 (14) |
C31—C32—C33—C5A | −179.5 (10) | N6—C5B—C63—C64 | −142.7 (9) |
C5A—C33—C34—C35 | 175.8 (11) | C62—C63—C64—C65 | −2.8 (16) |
C32—C33—C34—C35 | −10.6 (17) | C5B—C63—C64—C65 | −177.2 (11) |
C33—C34—C35—C36 | 9 (2) | C63—C64—C65—C66 | −1.4 (19) |
C34—C35—C36—C31 | −3 (2) | C64—C65—C66—C61 | 6 (2) |
C32—C31—C36—C35 | −1.0 (18) | C62—C61—C66—C65 | −7 (2) |
C4A—C31—C36—C35 | −178.6 (12) | C4B—C61—C66—C65 | −171.2 (13) |
C5A—N3—C31A—N32A | −147.0 (9) | C5B—N6—C61A—N62A | −144.4 (9) |
C6A—N3—C31A—N32A | 14.5 (11) | C6B—N6—C61A—N62A | 18.9 (10) |
C5A—N3—C31A—C36A | 35.2 (13) | C5B—N6—C61A—C66A | 35.0 (12) |
C6A—N3—C31A—C36A | −163.3 (9) | C6B—N6—C61A—C66A | −161.7 (8) |
C36A—C31A—N32A—C33A | 0.6 (14) | C66A—C61A—N62A—C63A | 0.5 (13) |
N3—C31A—N32A—C33A | −177.1 (7) | N6—C61A—N62A—C63A | 179.9 (7) |
C31A—N32A—C33A—C34A | −5.5 (14) | C61A—N62A—C63A—C64A | −2.1 (13) |
N32A—C33A—C34A—C35A | 6.4 (14) | N62A—C63A—C64A—C65A | 0.5 (14) |
N32A—C33A—C34A—C37A | −176.3 (9) | N62A—C63A—C64A—C67A | −179.1 (8) |
C33A—C34A—C35A—C36A | −2.5 (14) | C63A—C64A—C65A—C66A | 2.5 (15) |
C37A—C34A—C35A—C36A | −179.8 (9) | C67A—C64A—C65A—C66A | −178.0 (9) |
N32A—C31A—C36A—C35A | 2.9 (15) | N62A—C61A—C66A—C65A | 2.2 (13) |
N3—C31A—C36A—C35A | −179.5 (8) | N6—C61A—C66A—C65A | −177.1 (7) |
C34A—C35A—C36A—C31A | −1.9 (14) | C64A—C65A—C66A—C61A | −3.7 (14) |
C33A—C34A—C37A—O31A | 174.1 (11) | C65A—C64A—C67A—O61A | −10.9 (15) |
C35A—C34A—C37A—O31A | −8.7 (17) | C63A—C64A—C67A—O61A | 168.7 (9) |
C33A—C34A—C37A—O32A | −7.0 (15) | C65A—C64A—C67A—O62A | 172.1 (10) |
C35A—C34A—C37A—O32A | 170.1 (10) | C63A—C64A—C67A—O62A | −8.3 (13) |
O31A—C37A—O32A—C38A | −5.3 (18) | O61A—C67A—O62A—C68A | −3.2 (18) |
C34A—C37A—O32A—C38A | 175.9 (8) | C64A—C67A—O62A—C68A | 173.2 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C35A—H35A···O31Ai | 0.93 | 2.36 | 3.204 (13) | 150 |
C65A—H65A···O61Aii | 0.93 | 2.41 | 3.227 (14) | 146 |
C12—H12···N3 | 0.93 | 2.58 | 2.907 (12) | 101 |
C22—H22···N1 | 0.93 | 2.57 | 2.886 (14) | 100 |
C23A—H23A···O22A | 0.93 | 2.42 | 2.736 (17) | 100 |
C28A—H28A···O21A | 0.96 | 2.24 | 2.68 (2) | 107 |
C33A—H33A···O32A | 0.93 | 2.40 | 2.731 (14) | 101 |
C36A—H36A···O5A | 0.93 | 2.45 | 2.843 (13) | 105 |
C38A—H38A···O31A | 0.96 | 2.19 | 2.630 (17) | 107 |
C48A—H48A···O41A | 0.96 | 2.28 | 2.642 (16) | 101 |
C55—H55···O3A | 0.93 | 2.59 | 3.377 (14) | 143 |
C55A—H55A···O52A | 0.93 | 2.41 | 2.735 (14) | 100 |
C63A—H63A···O62A | 0.93 | 2.40 | 2.726 (13) | 100 |
C66A—H66A···O5B | 0.93 | 2.52 | 2.858 (13) | 101 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z. |
Experimental details
| (EsIO4_I_12-001) | (EsIO3_II_12-015_Squeeze) |
Crystal data |
Chemical formula | C60H40N8O16 | C45H30N6O12 |
Mr | 1129.00 | 846.75 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 294 | 294 |
a, b, c (Å) | 10.6870 (1), 22.4852 (2), 22.6756 (2) | 16.3411 (13), 16.5747 (4), 17.4806 (16) |
α, β, γ (°) | 90, 101.721 (1), 90 | 87.273 (5), 83.350 (7), 89.825 (4) |
V (Å3) | 5335.31 (8) | 4697.4 (6) |
Z | 4 | 4 |
Radiation type | Cu Kα | Cu Kα |
µ (mm−1) | 0.88 | 0.75 |
Crystal size (mm) | 0.58 × 0.06 × 0.05 | 0.60 × 0.08 × 0.02 |
|
Data collection |
Diffractometer | Xcalibur, Sapphire3, Gemini Ultra diffractometer | Xcalibur, Sapphire3, Gemini Ultra diffractometer |
Absorption correction | Analytical (ABSFAC, Clark and Reid, 1998) | Analytical (ABSFAC, Clark and Reid, 1998) |
Tmin, Tmax | 0.631, 0.958 | 0.663, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31765, 8619, 6947 | 16648, 10048, 4137 |
Rint | 0.034 | 0.083 |
θmax (°) | 63.3 | 51.4 |
(sin θ/λ)max (Å−1) | 0.579 | 0.507 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.120, 1.03 | 0.121, 0.352, 0.91 |
No. of reflections | 8619 | 10048 |
No. of parameters | 762 | 1141 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.17 | 0.47, −0.35 |
Hydrogen-bond geometry (Å, º) for (EsIO4_I_12-001) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4A—H4A2···O5i | 0.96 | 2.56 | 3.491 (4) | 165 |
C6A—H6A3···O3ii | 0.96 | 2.58 | 3.461 (4) | 153 |
C26A—H26A···O5Aii | 0.93 | 2.42 | 3.333 (3) | 167 |
C15A—H15A···O4iii | 0.93 | 2.38 | 3.133 (3) | 138 |
C35A—H35A···O7iv | 0.93 | 2.57 | 3.107 (3) | 117 |
C36—H36···O6v | 0.93 | 2.48 | 3.400 (2) | 171 |
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1/2, y+1/2, −z+1/2; (v) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (EsIO3_II_12-015_Squeeze) top
D—H···A | D—H | H···A | D···A | D—H···A |
C35A—H35A···O31Ai | 0.93 | 2.36 | 3.204 (13) | 150 |
C65A—H65A···O61Aii | 0.93 | 2.41 | 3.227 (14) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y, −z. |
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