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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519212047410/gp5057sup1.cif
Contains datablocks global, EsIO4_I_12-001, EsIO3_II_12-015_Squeeze

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212047410/gp5057EsIO4_I_12-001sup2.hkl
Contains datablock (EsIO)4_12-001

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519212047410/gp5057EsIO3_II_12-015_Squeezesup3.hkl
Contains datablock (EsIO)3_12-015_SQUEEZE

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519212047410/gp5057sup4.pdf
(EsIO)3 and (EsIO)4 spectroscopic and crystallographic data

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(EsIO4_I_12-001) top
Crystal data top
C60H40N8O16F(000) = 2336
Mr = 1129.00Dx = 1.406 Mg m3
Monoclinic, P21/nMelting point: 476 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54184 Å
a = 10.6870 (1) ÅCell parameters from 11636 reflections
b = 22.4852 (2) Åθ = 2.8–63.1°
c = 22.6756 (2) ŵ = 0.88 mm1
β = 101.721 (1)°T = 294 K
V = 5335.31 (8) Å3Needle, colourless
Z = 40.58 × 0.06 × 0.05 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
8619 independent reflections
Radiation source: Enhance (Cu) X-ray Source6947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 63.3°, θmin = 2.8°
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
h = 1112
Tmin = 0.631, Tmax = 0.958k = 2425
31765 measured reflectionsl = 2621
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-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 reflectionsΔρmax = 0.27 e Å3
762 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00038 (5)
Crystal data top
C60H40N8O16V = 5335.31 (8) Å3
Mr = 1129.00Z = 4
Monoclinic, P21/nCu Kα radiation
a = 10.6870 (1) ŵ = 0.88 mm1
b = 22.4852 (2) ÅT = 294 K
c = 22.6756 (2) Å0.58 × 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 = 0.958Rint = 0.034
31765 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.03Δρmax = 0.27 e Å3
8619 reflectionsΔρmin = 0.17 e Å3
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
xyzUiso*/Ueq
O10.15831 (17)0.18857 (7)0.46844 (7)0.0612 (4)
C10.2011 (2)0.18789 (9)0.42307 (9)0.0464 (5)
N10.30161 (16)0.22599 (8)0.41630 (7)0.0479 (4)
O20.45380 (16)0.28347 (9)0.47432 (8)0.0757 (5)
C20.3421 (2)0.27245 (10)0.45862 (9)0.0517 (5)
O30.07174 (15)0.44529 (6)0.39841 (7)0.0563 (4)
C30.05505 (19)0.39251 (9)0.40628 (9)0.0433 (4)
N20.13146 (15)0.35051 (7)0.36964 (7)0.0427 (4)
O40.31578 (15)0.34468 (8)0.29957 (9)0.0745 (5)
C40.21277 (18)0.36745 (9)0.31491 (10)0.0459 (5)
O50.14918 (15)0.44217 (8)0.15956 (7)0.0620 (4)
C50.13048 (19)0.43811 (8)0.21004 (9)0.0413 (4)
N30.23290 (14)0.42727 (7)0.25862 (7)0.0393 (4)
O60.44817 (13)0.43474 (7)0.26451 (7)0.0571 (4)
C60.35088 (18)0.40900 (8)0.24366 (9)0.0408 (4)
O70.24172 (16)0.15482 (6)0.18935 (8)0.0616 (4)
C70.1926 (2)0.20376 (8)0.18419 (9)0.0436 (4)
N40.06544 (15)0.20986 (7)0.18926 (7)0.0405 (4)
O80.07996 (16)0.13342 (7)0.17083 (7)0.0669 (5)
C80.00609 (19)0.15568 (8)0.20559 (9)0.0444 (5)
C110.05471 (19)0.13301 (8)0.26695 (9)0.0417 (4)
C120.11227 (18)0.17018 (8)0.31334 (8)0.0407 (4)
H120.12740.20980.30550.049*
C130.14713 (19)0.14824 (9)0.37129 (9)0.0438 (4)
C140.1284 (2)0.08870 (9)0.38258 (10)0.0553 (5)
H140.15240.07390.42150.066*
C150.0743 (3)0.05144 (10)0.33620 (11)0.0645 (7)
H150.06350.01130.34380.077*
C160.0359 (2)0.07337 (9)0.27849 (10)0.0549 (5)
H160.00240.04830.24740.066*
C11A0.38579 (19)0.21038 (9)0.37715 (9)0.0463 (5)
N12A0.40890 (18)0.15260 (8)0.37348 (8)0.0527 (4)
C13A0.4729 (2)0.13613 (10)0.33154 (10)0.0535 (5)
H13A0.48670.09570.32680.064*
C14A0.52007 (19)0.17554 (9)0.29475 (10)0.0491 (5)
C15A0.5028 (2)0.23589 (10)0.30320 (10)0.0539 (5)
H15A0.53820.26380.28110.065*
C16A0.4330 (2)0.25374 (10)0.34449 (10)0.0526 (5)
H16A0.41780.29380.35030.063*
O1A0.6420 (2)0.18734 (9)0.21920 (11)0.1021 (8)
C1A0.5839 (2)0.15541 (11)0.24621 (11)0.0603 (6)
C2A0.6155 (3)0.07496 (14)0.18517 (13)0.0856 (9)
H2A10.57750.09570.14900.128*
H2A20.59620.03330.18030.128*
H2A30.70640.08050.19310.128*
O2A0.56501 (18)0.09792 (7)0.23468 (8)0.0699 (5)
C210.2427 (2)0.30939 (9)0.47743 (9)0.0479 (5)
C220.13017 (19)0.32416 (8)0.43767 (9)0.0430 (4)
H220.10750.30440.40110.052*
C230.05146 (19)0.36851 (9)0.45256 (9)0.0458 (5)
C240.0838 (2)0.39644 (12)0.50825 (11)0.0659 (6)
H240.03190.42640.51840.079*
C250.1930 (3)0.37971 (14)0.54847 (11)0.0771 (8)
H250.21270.39740.58630.093*
C260.2731 (2)0.33695 (12)0.53308 (10)0.0645 (6)
H260.34760.32660.56010.077*
C21A0.16031 (18)0.29351 (8)0.39325 (9)0.0410 (4)
N22A0.13026 (16)0.24697 (7)0.36253 (8)0.0481 (4)
C23A0.1622 (2)0.19371 (9)0.38118 (10)0.0476 (5)
H23A0.14320.16030.36040.057*
C24A0.22132 (19)0.18503 (8)0.42920 (9)0.0428 (4)
C25A0.2507 (2)0.23456 (9)0.46015 (10)0.0512 (5)
H25A0.29060.23050.49270.061*
C26A0.2190 (2)0.29017 (9)0.44140 (10)0.0528 (5)
H26A0.23730.32440.46110.063*
O3A0.2326 (2)0.08049 (7)0.41664 (8)0.0762 (5)
C3A0.2554 (2)0.12334 (9)0.44377 (10)0.0489 (5)
C4A0.3591 (4)0.06359 (12)0.50494 (16)0.0993 (12)
H4A10.43730.05380.47750.149*
H4A20.37380.06470.54530.149*
H4A30.29570.03400.50220.149*
O4A0.3145 (2)0.12144 (7)0.48944 (8)0.0736 (5)
C310.16309 (17)0.40963 (8)0.27486 (9)0.0396 (4)
C320.03647 (17)0.40921 (8)0.26872 (8)0.0384 (4)
H320.02380.38700.29510.046*
C330.00017 (18)0.44204 (8)0.22318 (8)0.0384 (4)
C340.09054 (19)0.47605 (9)0.18452 (9)0.0450 (5)
H340.06690.49710.15320.054*
C350.21488 (19)0.47864 (9)0.19256 (10)0.0489 (5)
H350.27380.50320.16820.059*
C360.25167 (19)0.44482 (9)0.23679 (9)0.0466 (5)
H360.33630.44550.24120.056*
C31A0.24288 (17)0.45518 (8)0.31615 (9)0.0393 (4)
N32A0.29189 (17)0.42068 (7)0.36269 (7)0.0471 (4)
C33A0.3098 (2)0.44536 (9)0.41730 (9)0.0501 (5)
H33A0.34640.42230.45040.060*
C34A0.2766 (2)0.50355 (9)0.42736 (10)0.0479 (5)
C35A0.2243 (2)0.53745 (9)0.37797 (10)0.0554 (5)
H35A0.19940.57640.38310.067*
C36A0.2088 (2)0.51362 (9)0.32106 (10)0.0506 (5)
H36A0.17650.53630.28710.061*
O5A0.2480 (2)0.57656 (9)0.49846 (9)0.0932 (7)
C5A0.2945 (2)0.53020 (11)0.48872 (11)0.0589 (6)
C6A0.3814 (3)0.51744 (16)0.59240 (12)0.0906 (10)
H6A10.41350.55740.59480.136*
H6A20.44090.49220.61840.136*
H6A30.30060.51660.60470.136*
O6A0.36492 (18)0.49632 (9)0.53073 (8)0.0727 (5)
C410.34559 (18)0.35574 (8)0.20463 (9)0.0412 (4)
C420.26049 (17)0.30969 (8)0.20754 (8)0.0387 (4)
H420.19860.31370.23080.046*
C430.26811 (18)0.25763 (8)0.17566 (9)0.0414 (4)
C440.3569 (2)0.25264 (10)0.13941 (10)0.0534 (5)
H440.36230.21760.11830.064*
C450.4379 (2)0.29944 (11)0.13421 (11)0.0611 (6)
H450.49450.29670.10810.073*
C460.4342 (2)0.35029 (10)0.16793 (10)0.0514 (5)
H460.49140.38110.16600.062*
C41A0.01798 (18)0.25496 (8)0.15947 (8)0.0393 (4)
N42A0.01418 (15)0.27914 (7)0.11119 (7)0.0450 (4)
C43A0.06151 (19)0.32277 (9)0.08422 (9)0.0461 (5)
H43A0.03910.34160.05140.055*
C44A0.17069 (18)0.34142 (8)0.10229 (8)0.0414 (4)
C45A0.2031 (2)0.31376 (9)0.15181 (9)0.0470 (5)
H45A0.27730.32450.16460.056*
C46A0.12450 (19)0.27053 (9)0.18160 (9)0.0460 (5)
H46A0.14240.25220.21570.055*
O7A0.21082 (15)0.42144 (7)0.03253 (7)0.0601 (4)
C7A0.2484 (2)0.38948 (9)0.06763 (9)0.0451 (5)
C8A0.4476 (3)0.43701 (13)0.04686 (12)0.0743 (8)
H8A10.40710.47530.05260.112*
H8A20.52660.43820.06080.112*
H8A30.46430.42690.00480.112*
O8A0.36477 (14)0.39304 (7)0.08034 (7)0.0562 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0883 (12)0.0569 (9)0.0402 (8)0.0023 (8)0.0177 (8)0.0020 (7)
C10.0572 (12)0.0431 (11)0.0373 (11)0.0079 (9)0.0058 (9)0.0059 (8)
N10.0537 (10)0.0470 (9)0.0398 (9)0.0027 (8)0.0019 (8)0.0055 (7)
O20.0506 (10)0.0993 (14)0.0687 (11)0.0036 (9)0.0076 (8)0.0306 (10)
C20.0536 (13)0.0560 (13)0.0393 (11)0.0045 (10)0.0052 (9)0.0036 (9)
O30.0702 (10)0.0384 (8)0.0591 (9)0.0002 (7)0.0103 (8)0.0013 (7)
C30.0476 (11)0.0402 (11)0.0441 (11)0.0022 (8)0.0138 (9)0.0011 (8)
N20.0426 (9)0.0374 (8)0.0463 (9)0.0031 (7)0.0049 (7)0.0058 (7)
O40.0444 (9)0.0718 (11)0.0969 (13)0.0200 (8)0.0104 (8)0.0328 (10)
C40.0370 (11)0.0410 (10)0.0571 (13)0.0020 (8)0.0036 (9)0.0065 (9)
O50.0600 (10)0.0840 (11)0.0443 (9)0.0131 (8)0.0164 (7)0.0142 (8)
C50.0449 (11)0.0393 (10)0.0397 (11)0.0012 (8)0.0091 (8)0.0026 (8)
N30.0365 (8)0.0402 (8)0.0412 (9)0.0009 (6)0.0083 (7)0.0042 (7)
O60.0410 (8)0.0557 (9)0.0762 (11)0.0101 (7)0.0157 (7)0.0162 (8)
C60.0384 (10)0.0390 (10)0.0460 (11)0.0034 (8)0.0112 (8)0.0006 (8)
O70.0690 (10)0.0387 (8)0.0800 (11)0.0105 (7)0.0222 (8)0.0017 (7)
C70.0524 (12)0.0388 (11)0.0382 (10)0.0037 (9)0.0057 (9)0.0027 (8)
N40.0430 (9)0.0344 (8)0.0410 (9)0.0014 (7)0.0015 (7)0.0055 (6)
O80.0757 (11)0.0550 (9)0.0570 (10)0.0229 (8)0.0171 (8)0.0085 (7)
C80.0502 (11)0.0371 (10)0.0417 (11)0.0047 (9)0.0007 (9)0.0012 (8)
C110.0466 (11)0.0367 (10)0.0402 (10)0.0009 (8)0.0049 (8)0.0036 (8)
C120.0446 (11)0.0345 (9)0.0419 (11)0.0013 (8)0.0057 (8)0.0036 (8)
C130.0506 (11)0.0425 (10)0.0370 (10)0.0030 (9)0.0061 (9)0.0023 (8)
C140.0763 (15)0.0465 (12)0.0406 (12)0.0013 (11)0.0061 (10)0.0095 (9)
C150.0992 (19)0.0371 (11)0.0534 (14)0.0091 (11)0.0067 (13)0.0091 (10)
C160.0753 (15)0.0370 (11)0.0485 (12)0.0083 (10)0.0032 (11)0.0017 (9)
C11A0.0474 (11)0.0476 (12)0.0399 (11)0.0034 (9)0.0007 (9)0.0020 (9)
N12A0.0602 (11)0.0467 (10)0.0518 (11)0.0089 (8)0.0130 (9)0.0052 (8)
C13A0.0570 (13)0.0463 (12)0.0581 (13)0.0070 (10)0.0143 (11)0.0034 (10)
C14A0.0421 (11)0.0515 (12)0.0516 (12)0.0003 (9)0.0047 (9)0.0011 (9)
C15A0.0526 (12)0.0526 (13)0.0541 (13)0.0098 (10)0.0052 (10)0.0044 (10)
C16A0.0586 (13)0.0443 (11)0.0518 (13)0.0018 (10)0.0036 (10)0.0012 (9)
O1A0.1188 (18)0.0823 (14)0.1288 (19)0.0153 (12)0.0811 (16)0.0038 (13)
C1A0.0551 (13)0.0645 (15)0.0644 (15)0.0024 (11)0.0196 (11)0.0064 (12)
C2A0.106 (2)0.088 (2)0.0753 (19)0.0105 (17)0.0476 (17)0.0042 (15)
O2A0.0875 (12)0.0603 (10)0.0710 (11)0.0001 (9)0.0373 (10)0.0038 (8)
C210.0535 (12)0.0501 (11)0.0370 (11)0.0013 (9)0.0017 (9)0.0027 (9)
C220.0501 (11)0.0432 (11)0.0337 (10)0.0045 (9)0.0041 (8)0.0031 (8)
C230.0490 (11)0.0474 (11)0.0404 (11)0.0026 (9)0.0076 (9)0.0036 (9)
C240.0662 (15)0.0788 (17)0.0531 (14)0.0086 (13)0.0132 (12)0.0201 (12)
C250.0755 (17)0.109 (2)0.0427 (13)0.0112 (16)0.0021 (12)0.0270 (14)
C260.0652 (15)0.0843 (17)0.0387 (12)0.0099 (13)0.0018 (10)0.0101 (11)
C21A0.0393 (10)0.0373 (10)0.0451 (11)0.0017 (8)0.0058 (8)0.0038 (8)
N22A0.0517 (10)0.0426 (9)0.0527 (10)0.0038 (7)0.0171 (8)0.0013 (8)
C23A0.0529 (12)0.0386 (10)0.0534 (12)0.0004 (9)0.0162 (10)0.0045 (9)
C24A0.0460 (11)0.0371 (10)0.0436 (11)0.0005 (8)0.0049 (9)0.0016 (8)
C25A0.0692 (14)0.0419 (11)0.0469 (12)0.0006 (10)0.0225 (10)0.0009 (9)
C26A0.0711 (14)0.0366 (11)0.0552 (13)0.0022 (10)0.0235 (11)0.0050 (9)
O3A0.1179 (15)0.0405 (9)0.0817 (12)0.0066 (9)0.0473 (11)0.0070 (8)
C3A0.0585 (13)0.0400 (11)0.0484 (12)0.0002 (9)0.0115 (10)0.0013 (9)
C4A0.158 (3)0.0497 (15)0.111 (3)0.0145 (17)0.077 (2)0.0125 (15)
O4A0.1177 (15)0.0417 (8)0.0746 (11)0.0040 (9)0.0503 (11)0.0041 (8)
C310.0361 (10)0.0372 (10)0.0430 (11)0.0016 (7)0.0020 (8)0.0017 (8)
C320.0369 (10)0.0365 (9)0.0387 (10)0.0010 (7)0.0002 (8)0.0012 (8)
C330.0384 (10)0.0371 (9)0.0379 (10)0.0015 (8)0.0031 (8)0.0025 (8)
C340.0481 (11)0.0418 (11)0.0425 (11)0.0007 (8)0.0032 (9)0.0053 (8)
C350.0433 (11)0.0469 (11)0.0514 (12)0.0065 (9)0.0023 (9)0.0102 (9)
C360.0340 (10)0.0471 (11)0.0556 (13)0.0016 (8)0.0018 (9)0.0045 (9)
C31A0.0356 (10)0.0388 (10)0.0435 (11)0.0035 (8)0.0079 (8)0.0022 (8)
N32A0.0568 (10)0.0389 (9)0.0443 (10)0.0038 (7)0.0073 (8)0.0026 (7)
C33A0.0595 (13)0.0466 (11)0.0427 (11)0.0021 (9)0.0067 (10)0.0034 (9)
C34A0.0516 (12)0.0444 (11)0.0495 (12)0.0061 (9)0.0145 (9)0.0089 (9)
C35A0.0682 (14)0.0384 (11)0.0609 (14)0.0028 (10)0.0160 (11)0.0097 (10)
C36A0.0571 (13)0.0396 (11)0.0541 (13)0.0036 (9)0.0087 (10)0.0017 (9)
O5A0.1380 (19)0.0680 (12)0.0766 (13)0.0156 (12)0.0285 (13)0.0255 (10)
C5A0.0647 (15)0.0589 (14)0.0568 (14)0.0084 (12)0.0214 (12)0.0161 (11)
C6A0.084 (2)0.132 (3)0.0532 (16)0.0015 (19)0.0090 (14)0.0286 (17)
O6A0.0762 (11)0.0894 (13)0.0500 (10)0.0063 (10)0.0070 (8)0.0193 (9)
C410.0393 (10)0.0420 (10)0.0424 (11)0.0007 (8)0.0083 (8)0.0008 (8)
C420.0381 (10)0.0408 (10)0.0379 (10)0.0034 (8)0.0091 (8)0.0007 (8)
C430.0406 (10)0.0407 (10)0.0409 (10)0.0012 (8)0.0033 (8)0.0012 (8)
C440.0557 (13)0.0538 (12)0.0523 (13)0.0028 (10)0.0150 (10)0.0127 (10)
C450.0570 (14)0.0724 (15)0.0612 (14)0.0060 (11)0.0291 (11)0.0132 (12)
C460.0450 (11)0.0558 (12)0.0570 (13)0.0068 (9)0.0190 (10)0.0065 (10)
C41A0.0452 (11)0.0350 (9)0.0345 (10)0.0039 (8)0.0003 (8)0.0004 (7)
N42A0.0453 (9)0.0480 (9)0.0408 (9)0.0018 (7)0.0065 (7)0.0061 (7)
C43A0.0499 (12)0.0448 (11)0.0417 (11)0.0014 (9)0.0046 (9)0.0110 (9)
C44A0.0419 (10)0.0396 (10)0.0390 (10)0.0018 (8)0.0004 (8)0.0012 (8)
C45A0.0454 (11)0.0497 (11)0.0448 (11)0.0033 (9)0.0065 (9)0.0024 (9)
C46A0.0496 (12)0.0482 (11)0.0398 (11)0.0000 (9)0.0084 (9)0.0086 (9)
O7A0.0687 (10)0.0498 (9)0.0595 (10)0.0010 (7)0.0077 (8)0.0163 (7)
C7A0.0520 (12)0.0398 (10)0.0400 (11)0.0012 (9)0.0008 (9)0.0004 (9)
C8A0.0709 (16)0.0835 (18)0.0655 (16)0.0344 (14)0.0065 (13)0.0175 (14)
O8A0.0560 (9)0.0600 (9)0.0504 (9)0.0153 (7)0.0060 (7)0.0096 (7)
Geometric parameters (Å, º) top
O1—C11.208 (2)N22A—C23A1.337 (3)
C1—N11.407 (3)C23A—C24A1.380 (3)
C1—C131.494 (3)C23A—H23A0.9300
N1—C21.425 (3)C24A—C25A1.386 (3)
N1—C11A1.430 (3)C24A—C3A1.488 (3)
O2—C21.201 (3)C25A—C26A1.384 (3)
C2—C211.478 (3)C25A—H25A0.9300
O3—C31.208 (2)C26A—H26A0.9300
C3—N21.405 (3)O3A—C3A1.195 (3)
C3—C231.484 (3)C3A—O4A1.319 (3)
N2—C41.415 (3)C4A—O4A1.453 (3)
N2—C21A1.446 (2)C4A—H4A10.9600
O4—C41.200 (2)C4A—H4A20.9600
C4—C311.484 (3)C4A—H4A30.9600
O5—C51.205 (2)C31—C321.388 (3)
C5—N31.407 (2)C31—C361.391 (3)
C5—C331.488 (3)C32—C331.387 (3)
N3—C61.431 (2)C32—H320.9300
N3—C31A1.432 (2)C33—C341.394 (3)
O6—C61.200 (2)C34—C351.379 (3)
C6—C411.483 (3)C34—H340.9300
O7—C71.215 (2)C35—C361.378 (3)
C7—N41.393 (3)C35—H350.9300
C7—C431.490 (3)C36—H360.9300
N4—C41A1.427 (2)C31A—N32A1.329 (3)
N4—C81.456 (2)C31A—C36A1.374 (3)
O8—C81.193 (2)N32A—C33A1.335 (3)
C8—C111.474 (3)C33A—C34A1.386 (3)
C11—C121.386 (3)C33A—H33A0.9300
C11—C161.389 (3)C34A—C35A1.376 (3)
C12—C131.382 (3)C34A—C5A1.491 (3)
C12—H120.9300C35A—C36A1.376 (3)
C13—C141.385 (3)C35A—H35A0.9300
C14—C151.377 (3)C36A—H36A0.9300
C14—H140.9300O5A—C5A1.194 (3)
C15—C161.380 (3)C5A—O6A1.328 (3)
C15—H150.9300C6A—O6A1.453 (3)
C16—H160.9300C6A—H6A10.9600
C11A—N12A1.328 (3)C6A—H6A20.9600
C11A—C16A1.380 (3)C6A—H6A30.9600
N12A—C13A1.332 (3)C41—C461.388 (3)
C13A—C14A1.380 (3)C41—C421.389 (3)
C13A—H13A0.9300C42—C431.387 (3)
C14A—C15A1.388 (3)C42—H420.9300
C14A—C1A1.479 (3)C43—C441.381 (3)
C15A—C16A1.371 (3)C44—C451.382 (3)
C15A—H15A0.9300C44—H440.9300
C16A—H16A0.9300C45—C461.381 (3)
O1A—C1A1.196 (3)C45—H450.9300
C1A—O2A1.326 (3)C46—H460.9300
C2A—O2A1.437 (3)C41A—N42A1.328 (2)
C2A—H2A10.9600C41A—C46A1.379 (3)
C2A—H2A20.9600N42A—C43A1.338 (2)
C2A—H2A30.9600C43A—C44A1.378 (3)
C21—C261.384 (3)C43A—H43A0.9300
C21—C221.388 (3)C44A—C45A1.388 (3)
C22—C231.390 (3)C44A—C7A1.487 (3)
C22—H220.9300C45A—C46A1.370 (3)
C23—C241.390 (3)C45A—H45A0.9300
C24—C251.380 (4)C46A—H46A0.9300
C24—H240.9300O7A—C7A1.201 (2)
C25—C261.378 (4)C7A—O8A1.334 (2)
C25—H250.9300C8A—O8A1.437 (3)
C26—H260.9300C8A—H8A10.9600
C21A—N22A1.332 (3)C8A—H8A20.9600
C21A—C26A1.367 (3)C8A—H8A30.9600
O1—C1—N1120.98 (19)C23A—C24A—C3A118.63 (18)
O1—C1—C13121.7 (2)C25A—C24A—C3A123.09 (18)
N1—C1—C13117.33 (17)C26A—C25A—C24A118.41 (19)
C1—N1—C2120.45 (17)C26A—C25A—H25A120.8
C1—N1—C11A120.60 (17)C24A—C25A—H25A120.8
C2—N1—C11A117.07 (17)C21A—C26A—C25A118.38 (19)
O2—C2—N1119.9 (2)C21A—C26A—H26A120.8
O2—C2—C21121.9 (2)C25A—C26A—H26A120.8
N1—C2—C21117.97 (18)O3A—C3A—O4A123.96 (19)
O3—C3—N2121.49 (19)O3A—C3A—C24A123.6 (2)
O3—C3—C23122.06 (19)O4A—C3A—C24A112.47 (17)
N2—C3—C23116.35 (17)O4A—C4A—H4A1109.5
C3—N2—C4121.16 (16)O4A—C4A—H4A2109.5
C3—N2—C21A121.25 (16)H4A1—C4A—H4A2109.5
C4—N2—C21A115.10 (15)O4A—C4A—H4A3109.5
O4—C4—N2120.22 (18)H4A1—C4A—H4A3109.5
O4—C4—C31121.10 (19)H4A2—C4A—H4A3109.5
N2—C4—C31118.46 (16)C3A—O4A—C4A116.87 (19)
O5—C5—N3120.27 (18)C32—C31—C36119.73 (18)
O5—C5—C33121.95 (18)C32—C31—C4122.29 (17)
N3—C5—C33117.74 (16)C36—C31—C4117.41 (17)
C5—N3—C6116.53 (15)C33—C32—C31119.78 (17)
C5—N3—C31A122.64 (15)C33—C32—H32120.1
C6—N3—C31A115.83 (15)C31—C32—H32120.1
O6—C6—N3120.18 (17)C32—C33—C34119.83 (18)
O6—C6—C41123.34 (18)C32—C33—C5122.21 (17)
N3—C6—C41116.40 (16)C34—C33—C5117.71 (17)
O7—C7—N4119.41 (18)C35—C34—C33120.22 (18)
O7—C7—C43120.93 (19)C35—C34—H34119.9
N4—C7—C43119.59 (16)C33—C34—H34119.9
C7—N4—C41A123.85 (15)C36—C35—C34119.88 (18)
C7—N4—C8114.91 (15)C36—C35—H35120.1
C41A—N4—C8116.92 (15)C34—C35—H35120.1
O8—C8—N4120.03 (18)C35—C36—C31120.45 (18)
O8—C8—C11123.73 (18)C35—C36—H36119.8
N4—C8—C11116.18 (16)C31—C36—H36119.8
C12—C11—C16119.87 (18)N32A—C31A—C36A124.21 (18)
C12—C11—C8121.68 (17)N32A—C31A—N3114.33 (16)
C16—C11—C8118.37 (18)C36A—C31A—N3121.40 (18)
C13—C12—C11119.93 (18)C31A—N32A—C33A116.94 (17)
C13—C12—H12120.0N32A—C33A—C34A123.5 (2)
C11—C12—H12120.0N32A—C33A—H33A118.2
C12—C13—C14119.98 (19)C34A—C33A—H33A118.2
C12—C13—C1121.39 (17)C35A—C34A—C33A117.65 (19)
C14—C13—C1118.60 (18)C35A—C34A—C5A119.4 (2)
C15—C14—C13120.06 (19)C33A—C34A—C5A123.0 (2)
C15—C14—H14120.0C36A—C35A—C34A119.93 (19)
C13—C14—H14120.0C36A—C35A—H35A120.0
C14—C15—C16120.3 (2)C34A—C35A—H35A120.0
C14—C15—H15119.8C31A—C36A—C35A117.7 (2)
C16—C15—H15119.8C31A—C36A—H36A121.1
C15—C16—C11119.8 (2)C35A—C36A—H36A121.1
C15—C16—H16120.1O5A—C5A—O6A124.4 (2)
C11—C16—H16120.1O5A—C5A—C34A123.0 (2)
N12A—C11A—C16A124.4 (2)O6A—C5A—C34A112.7 (2)
N12A—C11A—N1115.30 (18)O6A—C6A—H6A1109.5
C16A—C11A—N1120.28 (18)O6A—C6A—H6A2109.5
C11A—N12A—C13A116.48 (19)H6A1—C6A—H6A2109.5
N12A—C13A—C14A123.8 (2)O6A—C6A—H6A3109.5
N12A—C13A—H13A118.1H6A1—C6A—H6A3109.5
C14A—C13A—H13A118.1H6A2—C6A—H6A3109.5
C13A—C14A—C15A118.0 (2)C5A—O6A—C6A116.3 (2)
C13A—C14A—C1A122.2 (2)C46—C41—C42119.74 (18)
C15A—C14A—C1A119.8 (2)C46—C41—C6118.76 (17)
C16A—C15A—C14A119.1 (2)C42—C41—C6121.32 (17)
C16A—C15A—H15A120.4C43—C42—C41119.77 (17)
C14A—C15A—H15A120.4C43—C42—H42120.1
C15A—C16A—C11A117.9 (2)C41—C42—H42120.1
C15A—C16A—H16A121.0C44—C43—C42119.93 (18)
C11A—C16A—H16A121.0C44—C43—C7117.87 (17)
O1A—C1A—O2A123.9 (2)C42—C43—C7121.86 (17)
O1A—C1A—C14A124.3 (2)C43—C44—C45120.46 (19)
O2A—C1A—C14A111.72 (19)C43—C44—H44119.8
O2A—C2A—H2A1109.5C45—C44—H44119.8
O2A—C2A—H2A2109.5C46—C45—C44119.6 (2)
H2A1—C2A—H2A2109.5C46—C45—H45120.2
O2A—C2A—H2A3109.5C44—C45—H45120.2
H2A1—C2A—H2A3109.5C45—C46—C41120.3 (2)
H2A2—C2A—H2A3109.5C45—C46—H46119.8
C1A—O2A—C2A116.0 (2)C41—C46—H46119.8
C26—C21—C22119.8 (2)N42A—C41A—C46A124.53 (18)
C26—C21—C2117.73 (19)N42A—C41A—N4116.09 (17)
C22—C21—C2121.68 (18)C46A—C41A—N4119.38 (17)
C21—C22—C23120.05 (18)C41A—N42A—C43A116.30 (17)
C21—C22—H22120.0N42A—C43A—C44A123.86 (18)
C23—C22—H22120.0N42A—C43A—H43A118.1
C22—C23—C24119.6 (2)C44A—C43A—H43A118.1
C22—C23—C3120.28 (17)C43A—C44A—C45A118.01 (18)
C24—C23—C3119.43 (19)C43A—C44A—C7A118.69 (17)
C25—C24—C23119.9 (2)C45A—C44A—C7A123.29 (18)
C25—C24—H24120.1C46A—C45A—C44A119.22 (19)
C23—C24—H24120.1C46A—C45A—H45A120.4
C26—C25—C24120.6 (2)C44A—C45A—H45A120.4
C26—C25—H25119.7C45A—C46A—C41A117.99 (18)
C24—C25—H25119.7C45A—C46A—H46A121.0
C25—C26—C21120.0 (2)C41A—C46A—H46A121.0
C25—C26—H26120.0O7A—C7A—O8A124.01 (19)
C21—C26—H26120.0O7A—C7A—C44A123.98 (19)
N22A—C21A—C26A124.94 (18)O8A—C7A—C44A112.00 (17)
N22A—C21A—N2114.24 (17)O8A—C8A—H8A1109.5
C26A—C21A—N2120.75 (17)O8A—C8A—H8A2109.5
C21A—N22A—C23A115.74 (17)H8A1—C8A—H8A2109.5
N22A—C23A—C24A124.31 (18)O8A—C8A—H8A3109.5
N22A—C23A—H23A117.8H8A1—C8A—H8A3109.5
C24A—C23A—H23A117.8H8A2—C8A—H8A3109.5
C23A—C24A—C25A118.23 (18)C7A—O8A—C8A115.33 (18)
O1—C1—N1—C29.7 (3)C26A—C21A—N22A—C23A0.5 (3)
C13—C1—N1—C2168.39 (17)N2—C21A—N22A—C23A176.45 (17)
O1—C1—N1—C11A154.23 (19)C21A—N22A—C23A—C24A0.6 (3)
C13—C1—N1—C11A27.7 (3)N22A—C23A—C24A—C25A0.4 (3)
C1—N1—C2—O2140.5 (2)N22A—C23A—C24A—C3A178.0 (2)
C11A—N1—C2—O224.0 (3)C23A—C24A—C25A—C26A0.1 (3)
C1—N1—C2—C2145.2 (3)C3A—C24A—C25A—C26A177.5 (2)
C11A—N1—C2—C21150.33 (19)N22A—C21A—C26A—C25A0.2 (3)
O3—C3—N2—C413.2 (3)N2—C21A—C26A—C25A176.57 (19)
C23—C3—N2—C4163.31 (17)C24A—C25A—C26A—C21A0.0 (3)
O3—C3—N2—C21A148.00 (19)C23A—C24A—C3A—O3A1.2 (3)
C23—C3—N2—C21A35.5 (2)C25A—C24A—C3A—O3A178.6 (2)
C3—N2—C4—O4142.5 (2)C23A—C24A—C3A—O4A178.2 (2)
C21A—N2—C4—O419.8 (3)C25A—C24A—C3A—O4A0.8 (3)
C3—N2—C4—C3142.9 (3)O3A—C3A—O4A—C4A3.1 (4)
C21A—N2—C4—C31154.83 (17)C24A—C3A—O4A—C4A176.3 (2)
O5—C5—N3—C613.0 (3)O4—C4—C31—C32139.2 (2)
C33—C5—N3—C6164.84 (16)N2—C4—C31—C3235.4 (3)
O5—C5—N3—C31A140.89 (19)O4—C4—C31—C3632.2 (3)
C33—C5—N3—C31A41.3 (2)N2—C4—C31—C36153.30 (19)
C5—N3—C6—O6127.8 (2)C36—C31—C32—C332.5 (3)
C31A—N3—C6—O627.9 (3)C4—C31—C32—C33168.61 (18)
C5—N3—C6—C4155.4 (2)C31—C32—C33—C341.1 (3)
C31A—N3—C6—C41148.91 (17)C31—C32—C33—C5173.04 (17)
O7—C7—N4—C41A150.95 (19)O5—C5—C33—C32145.4 (2)
C43—C7—N4—C41A32.1 (3)N3—C5—C33—C3232.4 (3)
O7—C7—N4—C84.9 (3)O5—C5—C33—C3428.9 (3)
C43—C7—N4—C8172.03 (17)N3—C5—C33—C34153.35 (17)
C7—N4—C8—O8114.6 (2)C32—C33—C34—C352.0 (3)
C41A—N4—C8—O843.0 (3)C5—C33—C34—C35176.44 (18)
C7—N4—C8—C1168.0 (2)C33—C34—C35—C363.7 (3)
C41A—N4—C8—C11134.40 (18)C34—C35—C36—C312.3 (3)
O8—C8—C11—C12152.3 (2)C32—C31—C36—C350.8 (3)
N4—C8—C11—C1224.9 (3)C4—C31—C36—C35170.72 (19)
O8—C8—C11—C1624.5 (3)C5—N3—C31A—N32A143.78 (18)
N4—C8—C11—C16158.29 (19)C6—N3—C31A—N32A62.2 (2)
C16—C11—C12—C132.0 (3)C5—N3—C31A—C36A38.9 (3)
C8—C11—C12—C13174.68 (19)C6—N3—C31A—C36A115.2 (2)
C11—C12—C13—C142.1 (3)C36A—C31A—N32A—C33A0.7 (3)
C11—C12—C13—C1175.73 (18)N3—C31A—N32A—C33A176.55 (17)
O1—C1—C13—C12128.9 (2)C31A—N32A—C33A—C34A1.9 (3)
N1—C1—C13—C1249.2 (3)N32A—C33A—C34A—C35A0.9 (3)
O1—C1—C13—C1449.0 (3)N32A—C33A—C34A—C5A178.6 (2)
N1—C1—C13—C14132.9 (2)C33A—C34A—C35A—C36A1.2 (3)
C12—C13—C14—C150.4 (3)C5A—C34A—C35A—C36A179.2 (2)
C1—C13—C14—C15177.5 (2)N32A—C31A—C36A—C35A1.3 (3)
C13—C14—C15—C161.4 (4)N3—C31A—C36A—C35A178.44 (19)
C14—C15—C16—C111.5 (4)C34A—C35A—C36A—C31A2.3 (3)
C12—C11—C16—C150.2 (3)C35A—C34A—C5A—O5A11.9 (4)
C8—C11—C16—C15176.6 (2)C33A—C34A—C5A—O5A167.7 (2)
C1—N1—C11A—N12A33.3 (3)C35A—C34A—C5A—O6A169.3 (2)
C2—N1—C11A—N12A131.2 (2)C33A—C34A—C5A—O6A11.1 (3)
C1—N1—C11A—C16A144.1 (2)O5A—C5A—O6A—C6A2.0 (4)
C2—N1—C11A—C16A51.4 (3)C34A—C5A—O6A—C6A176.8 (2)
C16A—C11A—N12A—C13A5.9 (3)O6—C6—C41—C4631.0 (3)
N1—C11A—N12A—C13A171.38 (18)N3—C6—C41—C46152.34 (18)
C11A—N12A—C13A—C14A3.1 (3)O6—C6—C41—C42144.2 (2)
N12A—C13A—C14A—C15A1.9 (3)N3—C6—C41—C4232.5 (3)
N12A—C13A—C14A—C1A176.2 (2)C46—C41—C42—C432.6 (3)
C13A—C14A—C15A—C16A4.3 (3)C6—C41—C42—C43172.50 (18)
C1A—C14A—C15A—C16A173.9 (2)C41—C42—C43—C442.5 (3)
C14A—C15A—C16A—C11A1.8 (3)C41—C42—C43—C7170.79 (18)
N12A—C11A—C16A—C15A3.6 (3)O7—C7—C43—C4438.6 (3)
N1—C11A—C16A—C15A173.61 (19)N4—C7—C43—C44144.54 (19)
C13A—C14A—C1A—O1A168.7 (3)O7—C7—C43—C42134.8 (2)
C15A—C14A—C1A—O1A13.2 (4)N4—C7—C43—C4242.1 (3)
C13A—C14A—C1A—O2A13.6 (3)C42—C43—C44—C450.5 (3)
C15A—C14A—C1A—O2A164.5 (2)C7—C43—C44—C45174.1 (2)
O1A—C1A—O2A—C2A2.1 (4)C43—C44—C45—C463.4 (4)
C14A—C1A—O2A—C2A175.6 (2)C44—C45—C46—C413.2 (4)
O2—C2—C21—C2631.0 (3)C42—C41—C46—C450.2 (3)
N1—C2—C21—C26154.7 (2)C6—C41—C46—C45175.4 (2)
O2—C2—C21—C22138.8 (2)C7—N4—C41A—N42A21.8 (3)
N1—C2—C21—C2235.4 (3)C8—N4—C41A—N42A133.57 (18)
C26—C21—C22—C233.1 (3)C7—N4—C41A—C46A158.30 (18)
C2—C21—C22—C23166.5 (2)C8—N4—C41A—C46A46.3 (2)
C21—C22—C23—C242.2 (3)C46A—C41A—N42A—C43A2.2 (3)
C21—C22—C23—C3168.33 (19)N4—C41A—N42A—C43A177.94 (16)
O3—C3—C23—C22131.0 (2)C41A—N42A—C43A—C44A2.7 (3)
N2—C3—C23—C2245.5 (3)N42A—C43A—C44A—C45A0.8 (3)
O3—C3—C23—C2439.6 (3)N42A—C43A—C44A—C7A178.57 (18)
N2—C3—C23—C24143.9 (2)C43A—C44A—C45A—C46A1.7 (3)
C22—C23—C24—C250.5 (4)C7A—C44A—C45A—C46A178.94 (19)
C3—C23—C24—C25171.1 (2)C44A—C45A—C46A—C41A2.2 (3)
C23—C24—C25—C262.4 (4)N42A—C41A—C46A—C45A0.2 (3)
C24—C25—C26—C211.6 (5)N4—C41A—C46A—C45A179.66 (17)
C22—C21—C26—C251.2 (4)C43A—C44A—C7A—O7A15.5 (3)
C2—C21—C26—C25168.8 (3)C45A—C44A—C7A—O7A165.2 (2)
C3—N2—C21A—N22A125.4 (2)C43A—C44A—C7A—O8A164.78 (17)
C4—N2—C21A—N22A72.3 (2)C45A—C44A—C7A—O8A14.6 (3)
C3—N2—C21A—C26A57.5 (3)O7A—C7A—O8A—C8A2.6 (3)
C4—N2—C21A—C26A104.8 (2)C44A—C7A—O8A—C8A177.70 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A2···O5i0.962.563.491 (4)165
C6A—H6A3···O3ii0.962.583.461 (4)153
C26A—H26A···O5Aii0.932.423.333 (3)167
C15A—H15A···O4iii0.932.383.133 (3)138
C35A—H35A···O7iv0.932.573.107 (3)117
C36—H36···O6v0.932.483.400 (2)171
C12—H12···N40.932.582.897 (2)100
C13A—H13A···O2A0.932.402.722 (3)100
C23A—H23A···O3A0.932.502.818 (3)100
C33A—H33A···O6A0.932.452.768 (3)100
Symmetry codes: (i) x1/2, 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) x1, y, z.
(EsIO3_II_12-015_Squeeze) top
Crystal data top
C45H30N6O12Z = 4
Mr = 846.75F(000) = 1752
Triclinic, P1Dx = 1.197 Mg m3
Hall symbol: -P 1Melting point: 490 K
a = 16.3411 (13) ÅCu Kα radiation, λ = 1.54184 Å
b = 16.5747 (4) ÅCell parameters from 784 reflections
c = 17.4806 (16) Åθ = 2.5–51.9°
α = 87.273 (5)°µ = 0.75 mm1
β = 83.350 (7)°T = 294 K
γ = 89.825 (4)°Lath, colourless
V = 4697.4 (6) Å30.60 × 0.08 × 0.02 mm
Data collection top
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
10048 independent reflections
Radiation source: Enhance (Cu) X-ray Source4137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
ω scansθmax = 51.4°, θmin = 2.6°
Absorption correction: analytical
(ABSFAC, Clark and Reid, 1998)
h = 1616
Tmin = 0.663, Tmax = 0.989k = 1616
16648 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.121Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.352H-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 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C45H30N6O12γ = 89.825 (4)°
Mr = 846.75V = 4697.4 (6) Å3
Triclinic, P1Z = 4
a = 16.3411 (13) ÅCu Kα radiation
b = 16.5747 (4) ŵ = 0.75 mm1
c = 17.4806 (16) ÅT = 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 = 0.989Rint = 0.083
16648 measured reflectionsθmax = 51.4°
Refinement top
R[F2 > 2σ(F2)] = 0.1210 restraints
wR(F2) = 0.352H-atom parameters constrained
S = 0.91Δρmax = 0.47 e Å3
10048 reflectionsΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
O1A0.2228 (5)0.1200 (4)0.8399 (5)0.092 (2)
C1A0.2783 (7)0.1529 (7)0.8633 (6)0.077 (3)
N10.2813 (5)0.2399 (4)0.8644 (5)0.070 (2)
O2A0.1973 (4)0.3425 (4)0.8332 (4)0.095 (2)
C2A0.2380 (6)0.2836 (6)0.8106 (7)0.079 (3)
O3A0.4657 (6)0.2004 (5)0.5448 (5)0.117 (3)
C3A0.4121 (9)0.1689 (7)0.5919 (7)0.094 (4)
N20.4155 (5)0.0920 (6)0.6183 (5)0.081 (2)
O4A0.4894 (5)0.0203 (5)0.5949 (5)0.119 (3)
C4A0.4907 (8)0.0515 (8)0.6092 (6)0.091 (3)
O5A0.6810 (4)0.2856 (4)0.7672 (4)0.094 (2)
C5A0.6413 (6)0.2246 (6)0.7708 (6)0.069 (3)
N30.5935 (5)0.1998 (4)0.8392 (5)0.070 (2)
O6A0.6379 (5)0.0658 (4)0.8466 (5)0.105 (3)
C6A0.5806 (7)0.1115 (6)0.8568 (5)0.073 (3)
C110.4934 (6)0.0893 (5)0.8811 (5)0.057 (2)
C120.4265 (6)0.1372 (5)0.8726 (5)0.063 (2)
H120.43480.19090.85560.075*
C130.3465 (5)0.1080 (5)0.8886 (5)0.059 (2)
C140.3325 (6)0.0282 (5)0.9186 (5)0.069 (3)
H140.27950.00710.92810.083*
C150.4008 (7)0.0181 (5)0.9336 (6)0.078 (3)
H150.39260.06850.95920.093*
C160.4792 (7)0.0088 (6)0.9117 (6)0.081 (3)
H160.52360.02560.91670.097*
C11A0.2930 (6)0.2726 (7)0.9344 (7)0.075 (3)
N12A0.2685 (5)0.2340 (5)0.9994 (6)0.078 (2)
C13A0.2741 (6)0.2675 (6)1.0656 (7)0.075 (3)
H13A0.25860.23871.11200.090*
C14A0.3036 (6)0.3467 (6)1.0655 (7)0.072 (3)
C15A0.3323 (6)0.3864 (7)0.9966 (8)0.085 (3)
H15A0.35260.43880.99570.102*
C16A0.3306 (6)0.3495 (7)0.9327 (7)0.080 (3)
H16A0.35400.37350.88620.097*
C17A0.2938 (6)0.3869 (8)1.1425 (9)0.086 (3)
O11A0.2856 (6)0.3495 (6)1.2028 (6)0.119 (3)
O12A0.3010 (5)0.4648 (5)1.1359 (5)0.113 (3)
C18A0.2859 (10)0.5080 (9)1.2107 (10)0.172 (7)
H18A0.30610.47551.25140.258*
H18B0.22790.51691.22300.258*
H18C0.31420.55901.20500.258*
C210.2527 (6)0.2670 (5)0.7280 (6)0.068 (3)
C220.3193 (6)0.2220 (6)0.7008 (6)0.078 (3)
H220.35220.19580.73410.094*
C230.3359 (6)0.2172 (7)0.6204 (7)0.086 (3)
C240.2870 (8)0.2594 (7)0.5734 (7)0.094 (3)
H240.30120.25990.52030.113*
C250.2193 (9)0.2998 (8)0.6012 (8)0.114 (4)
H250.18480.32310.56770.136*
C260.2022 (7)0.3062 (7)0.6769 (8)0.099 (4)
H260.15700.33640.69630.119*
C21A0.3410 (8)0.0461 (7)0.6329 (8)0.096 (3)
N22A0.2927 (7)0.0478 (6)0.5785 (5)0.099 (3)
C23A0.2259 (8)0.0041 (8)0.5906 (6)0.098 (3)
H23A0.19360.00130.55040.117*
C24A0.1989 (8)0.0392 (7)0.6603 (8)0.093 (4)
C25A0.2472 (10)0.0394 (7)0.7154 (10)0.114 (5)
H25A0.23170.06840.76160.137*
C26A0.3195 (10)0.0021 (7)0.7060 (7)0.103 (4)
H26A0.35370.00230.74490.123*
C27A0.1226 (9)0.0883 (9)0.6749 (11)0.113 (4)
O21A0.1048 (7)0.1296 (7)0.7297 (7)0.156 (4)
O22A0.0769 (6)0.0733 (6)0.6166 (7)0.139 (3)
C28A0.0046 (13)0.1212 (12)0.6184 (12)0.226 (11)
H28A0.00450.15170.66680.339*
H28B0.01110.15750.57700.339*
H28C0.04190.08670.61280.339*
C310.5685 (7)0.0902 (7)0.6248 (7)0.089 (3)
C320.5680 (7)0.1393 (6)0.6865 (6)0.081 (3)
H320.51820.14990.71560.098*
C330.6419 (7)0.1745 (6)0.7069 (7)0.081 (3)
C340.7123 (8)0.1630 (8)0.6553 (8)0.101 (4)
H340.75990.19160.66070.121*
C350.7129 (9)0.1118 (9)0.5985 (8)0.114 (4)
H350.76300.10030.57030.137*
C360.6433 (8)0.0754 (8)0.5797 (7)0.106 (4)
H360.64550.04190.53830.127*
C31A0.5759 (5)0.2482 (6)0.9031 (6)0.060 (2)
N32A0.5689 (5)0.2094 (5)0.9693 (5)0.075 (2)
C33A0.5478 (6)0.2537 (7)1.0338 (6)0.080 (3)
H33A0.53780.22611.08160.096*
C34A0.5410 (6)0.3363 (7)1.0307 (7)0.079 (3)
C35A0.5479 (6)0.3756 (6)0.9581 (7)0.081 (3)
H35A0.54150.43130.95330.097*
C36A0.5647 (7)0.3301 (7)0.8918 (7)0.093 (3)
H36A0.56810.35450.84250.112*
C37A0.5228 (8)0.3821 (10)1.1030 (9)0.098 (4)
O31A0.5236 (7)0.4546 (6)1.0991 (6)0.143 (4)
O32A0.5062 (4)0.3366 (5)1.1639 (6)0.104 (2)
C38A0.4941 (8)0.3777 (8)1.2346 (8)0.113 (4)
H38A0.50860.43371.22470.169*
H38B0.52830.35371.27060.169*
H38C0.43740.37341.25590.169*
O1B0.6815 (5)0.3806 (4)0.1606 (5)0.093 (2)
C1B0.7450 (7)0.3486 (5)0.1364 (6)0.069 (3)
N40.7461 (4)0.2615 (4)0.1340 (4)0.0625 (19)
O2B0.6536 (4)0.1608 (5)0.1637 (4)0.089 (2)
C2B0.6905 (7)0.2170 (7)0.1854 (6)0.075 (3)
O3B0.8543 (6)0.2858 (5)0.4513 (5)0.111 (3)
C3B0.8088 (7)0.3171 (8)0.4099 (7)0.088 (3)
N50.8263 (5)0.4005 (5)0.3822 (5)0.077 (2)
O4B0.8929 (5)0.5117 (5)0.4141 (5)0.119 (3)
C4B0.8987 (6)0.4482 (9)0.3942 (7)0.100 (4)
O5B1.1283 (4)0.2107 (4)0.2273 (4)0.089 (2)
C5B1.0870 (6)0.2740 (6)0.2262 (6)0.072 (3)
N61.0560 (4)0.2991 (4)0.1613 (5)0.068 (2)
O6B1.0991 (5)0.4303 (4)0.1530 (4)0.094 (2)
C6B1.0460 (6)0.3841 (5)0.1419 (6)0.068 (3)
C410.9662 (6)0.4111 (5)0.1173 (5)0.065 (2)
C420.8964 (6)0.3618 (5)0.1281 (5)0.062 (2)
H420.90040.30850.14650.074*
C430.8211 (6)0.3922 (6)0.1114 (6)0.071 (3)
C440.8146 (7)0.4725 (6)0.0797 (6)0.077 (3)
H440.76450.49320.06760.092*
C450.8871 (7)0.5194 (6)0.0675 (6)0.087 (3)
H450.88520.57150.04560.104*
C460.9611 (7)0.4889 (6)0.0877 (5)0.075 (3)
H461.00780.52160.08110.090*
C41A0.7774 (6)0.2300 (6)0.0642 (7)0.072 (3)
N42A0.7671 (4)0.2677 (5)0.0012 (6)0.073 (2)
C43A0.7881 (5)0.2341 (6)0.0640 (7)0.071 (3)
H43A0.78350.26410.10960.085*
C44A0.8182 (5)0.1535 (6)0.0700 (7)0.067 (3)
C45A0.8317 (6)0.1165 (6)0.0023 (8)0.082 (3)
H45A0.85370.06470.00250.098*
C46A0.8145 (6)0.1516 (6)0.0655 (6)0.073 (3)
H46A0.82620.12590.11150.088*
C47A0.8321 (6)0.1154 (7)0.1432 (8)0.078 (3)
O41A0.8352 (5)0.1519 (6)0.2059 (6)0.116 (3)
O42A0.8330 (5)0.0380 (5)0.1362 (5)0.115 (3)
C48A0.8378 (10)0.0074 (9)0.2086 (9)0.154 (6)
H48A0.86220.02650.25130.232*
H48B0.78330.02290.21780.232*
H48C0.87080.05480.20330.232*
C510.6854 (6)0.2355 (5)0.2690 (6)0.072 (3)
C520.7439 (6)0.2750 (6)0.3016 (6)0.073 (3)
H520.78600.30090.26920.088*
C530.7447 (6)0.2789 (6)0.3780 (6)0.072 (3)
C540.6787 (7)0.2413 (7)0.4272 (6)0.088 (3)
H540.67720.24310.48040.105*
C550.6162 (8)0.2016 (7)0.3951 (7)0.092 (3)
H550.57330.17700.42740.110*
C560.6173 (6)0.1987 (6)0.3190 (7)0.083 (3)
H560.57480.17340.29820.099*
C51A0.7547 (7)0.4498 (6)0.3686 (7)0.074 (3)
N52A0.7552 (6)0.4864 (6)0.3006 (6)0.099 (3)
C53A0.6845 (8)0.5308 (7)0.2878 (6)0.093 (3)
H53A0.68090.55590.23970.112*
C54A0.6208 (7)0.5376 (6)0.3451 (7)0.079 (3)
C55A0.6302 (7)0.4936 (6)0.4146 (7)0.093 (3)
H55A0.58760.49490.45470.112*
C56A0.6950 (6)0.4515 (5)0.4252 (5)0.065 (2)
H56A0.69910.42320.47190.078*
C57A0.5455 (8)0.5864 (7)0.3334 (9)0.100 (4)
O51A0.5411 (6)0.6268 (6)0.2756 (6)0.131 (3)
O52A0.4903 (5)0.5797 (5)0.3953 (5)0.115 (3)
C58A0.4127 (10)0.6276 (9)0.3867 (10)0.167 (7)
H58A0.38130.63150.43630.251*
H58B0.38040.60080.35290.251*
H58C0.42720.68080.36530.251*
C610.9789 (7)0.3977 (7)0.3810 (6)0.088 (3)
C620.9948 (6)0.3542 (6)0.3135 (6)0.079 (3)
H620.95290.34690.28280.095*
C631.0687 (6)0.3235 (5)0.2932 (5)0.068 (2)
C641.1317 (7)0.3326 (7)0.3419 (7)0.097 (3)
H641.18330.30960.33010.116*
C651.1145 (9)0.3762 (9)0.4072 (8)0.111 (4)
H651.15440.38190.44040.134*
C661.0413 (9)0.4100 (8)0.4227 (8)0.113 (4)
H661.03280.44350.46410.136*
C61A1.0513 (5)0.2496 (5)0.0946 (6)0.060 (2)
N62A1.0627 (5)0.2870 (4)0.0282 (5)0.068 (2)
C63A1.0598 (5)0.2471 (6)0.0363 (6)0.071 (3)
H63A1.06630.27490.08410.085*
C64A1.0467 (6)0.1628 (6)0.0317 (7)0.076 (3)
C65A1.0370 (6)0.1252 (6)0.0367 (8)0.083 (3)
H65A1.03050.06940.03960.099*
C66A1.0359 (6)0.1663 (6)0.1065 (6)0.075 (3)
H66A1.02600.14060.15520.090*
C67A1.0452 (6)0.1199 (9)0.1070 (10)0.096 (4)
O61A1.0472 (6)0.0446 (5)0.1001 (5)0.140 (4)
O62A1.0460 (5)0.1665 (5)0.1666 (5)0.099 (3)
C68A1.0540 (8)0.1295 (9)0.2406 (8)0.129 (5)
H68A1.01360.08740.23970.193*
H68B1.10820.10700.25060.193*
H68C1.04560.16950.28040.193*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.074 (5)0.065 (4)0.141 (6)0.000 (4)0.023 (4)0.012 (4)
C1A0.066 (7)0.077 (8)0.093 (8)0.015 (6)0.019 (6)0.015 (6)
N10.073 (5)0.053 (5)0.084 (6)0.006 (4)0.016 (4)0.007 (4)
O2A0.088 (5)0.081 (5)0.114 (6)0.033 (4)0.007 (4)0.009 (4)
C2A0.069 (7)0.063 (7)0.106 (9)0.002 (6)0.013 (6)0.013 (6)
O3A0.134 (7)0.107 (7)0.105 (6)0.019 (5)0.010 (6)0.008 (5)
C3A0.135 (12)0.067 (8)0.088 (9)0.017 (8)0.042 (8)0.010 (7)
N20.072 (6)0.069 (6)0.101 (6)0.009 (5)0.001 (5)0.011 (5)
O4A0.095 (6)0.096 (6)0.170 (8)0.004 (5)0.016 (5)0.050 (6)
C4A0.099 (9)0.075 (8)0.103 (8)0.006 (7)0.013 (6)0.033 (6)
O5A0.090 (5)0.063 (5)0.125 (6)0.011 (4)0.000 (4)0.003 (4)
C5A0.075 (7)0.046 (6)0.088 (8)0.005 (5)0.022 (6)0.010 (6)
N30.065 (5)0.042 (5)0.106 (7)0.010 (4)0.023 (5)0.007 (5)
O6A0.079 (5)0.064 (5)0.172 (8)0.038 (4)0.014 (5)0.010 (4)
C6A0.084 (8)0.048 (6)0.086 (7)0.013 (6)0.016 (6)0.004 (5)
C110.074 (7)0.042 (5)0.056 (5)0.010 (5)0.014 (4)0.000 (4)
C120.071 (7)0.038 (5)0.081 (6)0.003 (5)0.026 (5)0.011 (4)
C130.053 (6)0.044 (6)0.081 (6)0.002 (4)0.012 (5)0.009 (4)
C140.082 (7)0.045 (6)0.076 (6)0.012 (5)0.001 (5)0.003 (5)
C150.093 (8)0.037 (5)0.104 (8)0.015 (6)0.019 (6)0.008 (5)
C160.090 (8)0.051 (6)0.105 (8)0.007 (6)0.030 (6)0.004 (5)
C11A0.060 (6)0.070 (8)0.097 (9)0.018 (6)0.013 (6)0.020 (7)
N12A0.077 (6)0.064 (5)0.091 (7)0.006 (4)0.003 (5)0.008 (5)
C13A0.072 (7)0.059 (7)0.094 (8)0.006 (5)0.008 (5)0.019 (6)
C14A0.049 (6)0.071 (7)0.098 (8)0.019 (5)0.015 (5)0.016 (6)
C15A0.073 (7)0.071 (7)0.110 (10)0.010 (5)0.008 (7)0.004 (8)
C16A0.083 (7)0.069 (8)0.086 (8)0.013 (6)0.001 (6)0.012 (6)
C17A0.054 (6)0.074 (9)0.131 (12)0.002 (6)0.011 (7)0.009 (8)
O11A0.109 (7)0.109 (7)0.143 (8)0.003 (5)0.025 (6)0.025 (6)
O12A0.100 (6)0.079 (6)0.157 (8)0.019 (4)0.009 (5)0.043 (5)
C18A0.153 (14)0.125 (12)0.238 (19)0.032 (10)0.018 (13)0.102 (13)
C210.068 (7)0.047 (5)0.091 (7)0.001 (5)0.009 (6)0.016 (5)
C220.081 (7)0.071 (7)0.081 (8)0.003 (6)0.009 (6)0.008 (5)
C230.057 (6)0.089 (8)0.114 (10)0.010 (6)0.008 (6)0.019 (7)
C240.096 (9)0.106 (9)0.084 (8)0.018 (7)0.024 (7)0.001 (7)
C250.127 (12)0.107 (10)0.109 (11)0.026 (9)0.030 (9)0.000 (8)
C260.085 (8)0.098 (9)0.120 (11)0.049 (7)0.031 (8)0.028 (7)
C21A0.100 (10)0.081 (8)0.108 (10)0.014 (7)0.008 (8)0.018 (7)
N22A0.104 (8)0.116 (8)0.082 (7)0.004 (6)0.031 (6)0.005 (5)
C23A0.098 (9)0.119 (10)0.074 (8)0.020 (8)0.004 (7)0.002 (7)
C24A0.087 (9)0.093 (9)0.099 (10)0.006 (7)0.014 (8)0.009 (7)
C25A0.111 (11)0.065 (8)0.157 (14)0.009 (8)0.032 (11)0.006 (8)
C26A0.143 (12)0.084 (8)0.084 (9)0.035 (9)0.026 (8)0.002 (7)
C27A0.103 (12)0.097 (11)0.131 (14)0.009 (9)0.011 (10)0.017 (9)
O21A0.134 (9)0.148 (9)0.171 (11)0.011 (7)0.030 (7)0.018 (8)
O22A0.118 (7)0.111 (7)0.188 (10)0.036 (6)0.021 (7)0.024 (6)
C28A0.23 (2)0.21 (2)0.24 (2)0.175 (19)0.068 (17)0.080 (16)
C310.093 (9)0.077 (7)0.101 (8)0.004 (6)0.020 (7)0.018 (6)
C320.086 (8)0.066 (6)0.091 (8)0.000 (6)0.002 (6)0.017 (6)
C330.071 (7)0.073 (7)0.100 (8)0.003 (6)0.013 (7)0.005 (6)
C340.088 (9)0.108 (10)0.109 (9)0.002 (7)0.014 (8)0.019 (8)
C350.093 (10)0.120 (11)0.127 (11)0.016 (8)0.013 (8)0.001 (9)
C360.085 (9)0.113 (10)0.121 (10)0.012 (7)0.009 (8)0.033 (8)
C31A0.064 (6)0.045 (6)0.074 (7)0.005 (4)0.016 (5)0.002 (6)
N32A0.085 (6)0.054 (5)0.090 (6)0.001 (4)0.030 (5)0.005 (5)
C33A0.075 (7)0.074 (8)0.093 (8)0.011 (5)0.015 (6)0.001 (6)
C34A0.056 (6)0.068 (7)0.116 (9)0.011 (5)0.019 (6)0.010 (7)
C35A0.070 (7)0.056 (6)0.115 (9)0.017 (5)0.017 (6)0.008 (7)
C36A0.089 (8)0.078 (8)0.112 (9)0.009 (6)0.013 (7)0.013 (7)
C37A0.102 (9)0.089 (10)0.112 (11)0.032 (8)0.039 (8)0.035 (9)
O31A0.198 (10)0.086 (6)0.162 (8)0.068 (7)0.076 (7)0.050 (6)
O32A0.075 (5)0.105 (6)0.131 (7)0.003 (4)0.005 (5)0.028 (6)
C38A0.101 (9)0.113 (10)0.128 (11)0.007 (7)0.019 (8)0.040 (8)
O1B0.076 (5)0.053 (4)0.146 (7)0.012 (4)0.005 (4)0.001 (4)
C1B0.071 (7)0.047 (6)0.094 (7)0.013 (5)0.027 (5)0.015 (5)
N40.059 (5)0.049 (5)0.081 (6)0.008 (4)0.011 (4)0.005 (4)
O2B0.084 (5)0.081 (5)0.103 (5)0.024 (4)0.016 (4)0.004 (4)
C2B0.080 (7)0.065 (7)0.079 (8)0.007 (6)0.003 (6)0.001 (6)
O3B0.120 (7)0.104 (6)0.111 (6)0.019 (5)0.026 (5)0.017 (5)
C3B0.077 (8)0.104 (10)0.084 (8)0.023 (7)0.010 (7)0.017 (7)
N50.057 (5)0.082 (6)0.096 (6)0.007 (5)0.017 (4)0.024 (5)
O4B0.103 (6)0.075 (5)0.186 (9)0.009 (5)0.017 (5)0.075 (6)
C4B0.060 (7)0.116 (10)0.124 (10)0.007 (7)0.005 (6)0.039 (8)
O5B0.075 (5)0.082 (5)0.112 (6)0.017 (4)0.016 (4)0.010 (4)
C5B0.060 (6)0.065 (7)0.092 (8)0.007 (5)0.015 (6)0.004 (6)
N60.061 (5)0.054 (5)0.090 (6)0.003 (4)0.013 (4)0.000 (4)
O6B0.084 (5)0.064 (5)0.135 (6)0.021 (4)0.018 (4)0.001 (4)
C6B0.067 (7)0.026 (5)0.109 (8)0.005 (5)0.008 (5)0.003 (5)
C410.068 (7)0.039 (6)0.088 (7)0.003 (5)0.004 (5)0.009 (5)
C420.060 (6)0.047 (5)0.076 (6)0.004 (5)0.002 (5)0.001 (4)
C430.068 (7)0.055 (6)0.091 (7)0.005 (5)0.013 (5)0.010 (5)
C440.088 (8)0.049 (6)0.092 (7)0.001 (6)0.005 (6)0.004 (5)
C450.102 (9)0.051 (6)0.105 (8)0.016 (6)0.000 (7)0.015 (5)
C460.072 (7)0.057 (7)0.094 (7)0.003 (5)0.002 (6)0.002 (5)
C41A0.084 (7)0.057 (7)0.074 (7)0.009 (5)0.009 (6)0.001 (6)
N42A0.053 (5)0.069 (6)0.100 (7)0.000 (4)0.005 (5)0.030 (6)
C43A0.056 (6)0.055 (7)0.100 (8)0.001 (5)0.007 (5)0.001 (6)
C44A0.053 (6)0.060 (7)0.092 (8)0.007 (5)0.023 (5)0.001 (6)
C45A0.077 (7)0.055 (6)0.115 (10)0.013 (5)0.016 (7)0.006 (7)
C46A0.076 (7)0.059 (7)0.087 (8)0.002 (5)0.021 (5)0.005 (6)
C47A0.062 (6)0.062 (8)0.115 (10)0.002 (5)0.030 (6)0.014 (7)
O41A0.114 (7)0.105 (7)0.135 (8)0.007 (5)0.028 (6)0.028 (6)
O42A0.121 (6)0.064 (5)0.167 (8)0.021 (4)0.031 (5)0.049 (5)
C48A0.165 (14)0.111 (11)0.207 (16)0.031 (10)0.072 (12)0.088 (11)
C510.068 (7)0.048 (6)0.101 (8)0.006 (5)0.014 (6)0.002 (5)
C520.074 (7)0.068 (7)0.074 (8)0.004 (5)0.000 (6)0.002 (5)
C530.060 (7)0.080 (7)0.074 (8)0.009 (5)0.004 (6)0.003 (5)
C540.079 (8)0.100 (8)0.084 (8)0.014 (6)0.009 (7)0.009 (6)
C550.102 (9)0.106 (9)0.065 (8)0.002 (7)0.001 (7)0.004 (6)
C560.064 (7)0.061 (6)0.124 (10)0.010 (5)0.017 (6)0.002 (6)
C51A0.079 (8)0.059 (6)0.083 (8)0.012 (5)0.008 (7)0.004 (6)
N52A0.103 (8)0.087 (7)0.104 (8)0.007 (6)0.001 (6)0.006 (6)
C53A0.093 (9)0.114 (9)0.072 (7)0.000 (7)0.007 (7)0.000 (6)
C54A0.092 (8)0.059 (6)0.088 (8)0.001 (6)0.016 (7)0.004 (6)
C55A0.080 (8)0.068 (7)0.128 (11)0.010 (6)0.002 (7)0.010 (7)
C56A0.074 (7)0.069 (6)0.050 (6)0.014 (5)0.004 (5)0.007 (4)
C57A0.099 (10)0.081 (9)0.117 (11)0.014 (7)0.007 (9)0.005 (8)
O51A0.142 (8)0.128 (7)0.119 (7)0.008 (6)0.020 (6)0.052 (6)
O52A0.094 (6)0.098 (6)0.145 (7)0.025 (5)0.000 (5)0.032 (5)
C58A0.134 (13)0.121 (12)0.227 (18)0.046 (10)0.039 (12)0.046 (11)
C610.080 (8)0.097 (8)0.089 (8)0.003 (6)0.013 (6)0.018 (6)
C620.060 (7)0.081 (7)0.098 (8)0.006 (5)0.003 (5)0.024 (6)
C630.076 (7)0.054 (6)0.073 (6)0.003 (5)0.008 (6)0.009 (5)
C640.087 (8)0.102 (9)0.105 (9)0.004 (6)0.021 (7)0.013 (7)
C650.090 (10)0.134 (11)0.116 (10)0.009 (8)0.026 (7)0.032 (9)
C660.094 (10)0.117 (10)0.135 (11)0.000 (8)0.020 (9)0.049 (8)
C61A0.046 (5)0.049 (6)0.083 (7)0.006 (4)0.007 (5)0.000 (6)
N62A0.084 (6)0.036 (4)0.080 (6)0.003 (4)0.003 (4)0.001 (4)
C63A0.060 (6)0.057 (7)0.095 (8)0.002 (5)0.003 (5)0.014 (6)
C64A0.067 (7)0.055 (7)0.106 (9)0.007 (5)0.006 (6)0.010 (6)
C65A0.077 (7)0.052 (6)0.118 (10)0.008 (5)0.006 (6)0.003 (7)
C66A0.065 (6)0.063 (7)0.095 (8)0.006 (5)0.000 (5)0.003 (6)
C67A0.052 (6)0.080 (10)0.158 (13)0.005 (6)0.008 (7)0.064 (9)
O61A0.198 (10)0.072 (6)0.140 (7)0.072 (6)0.037 (6)0.038 (5)
O62A0.106 (6)0.091 (6)0.106 (6)0.025 (5)0.030 (5)0.014 (5)
C68A0.106 (10)0.142 (12)0.138 (12)0.020 (8)0.002 (8)0.049 (10)
Geometric parameters (Å, º) top
O1A—C1A1.182 (11)O1B—C1B1.204 (11)
C1A—C131.438 (13)C1B—N41.447 (11)
C1A—N11.445 (13)C1B—C431.453 (14)
N1—C11A1.395 (12)N4—C2B1.388 (12)
N1—C2A1.413 (13)N4—C41A1.393 (12)
O2A—C2A1.235 (11)O2B—C2B1.212 (11)
C2A—C211.475 (14)C2B—C511.500 (14)
O3A—C3A1.230 (14)O3B—C3B1.197 (12)
C3A—N21.338 (13)C3B—C531.408 (15)
C3A—C231.526 (16)C3B—N51.461 (15)
N2—C4A1.394 (14)N5—C51A1.460 (13)
N2—C21A1.430 (15)N5—C4B1.465 (14)
O4A—C4A1.229 (12)O4B—C4B1.124 (12)
C4A—C311.485 (15)C4B—C611.553 (16)
O5A—C5A1.198 (11)O5B—C5B1.245 (11)
C5A—N31.396 (12)C5B—N61.344 (12)
C5A—C331.422 (14)C5B—C631.465 (13)
N3—C31A1.407 (12)N6—C6B1.447 (11)
N3—C6A1.492 (11)N6—C61A1.466 (12)
O6A—C6A1.205 (11)O6B—C6B1.197 (10)
C6A—C111.481 (13)C6B—C411.481 (13)
C11—C121.367 (12)C41—C461.374 (12)
C11—C161.423 (12)C41—C421.394 (12)
C12—C131.389 (12)C42—C431.385 (12)
C12—H120.9300C42—H420.9300
C13—C141.408 (12)C43—C441.425 (13)
C14—C151.396 (13)C44—C451.407 (14)
C14—H140.9300C44—H440.9300
C15—C161.365 (14)C45—C461.386 (14)
C15—H150.9300C45—H450.9300
C16—H160.9300C46—H460.9300
C11A—N12A1.298 (13)C41A—N42A1.304 (12)
C11A—C16A1.414 (14)C41A—C46A1.433 (13)
N12A—C13A1.319 (12)N42A—C43A1.266 (12)
C13A—C14A1.400 (13)C43A—C44A1.426 (13)
C13A—H13A0.9300C43A—H43A0.9300
C14A—C15A1.378 (14)C44A—C45A1.347 (13)
C14A—C17A1.522 (16)C44A—C47A1.448 (15)
C15A—C16A1.301 (14)C45A—C46A1.346 (13)
C15A—H15A0.9300C45A—H45A0.9300
C16A—H16A0.9300C46A—H46A0.9300
C17A—O11A1.191 (13)C47A—O41A1.221 (13)
C17A—O12A1.296 (13)C47A—O42A1.282 (12)
O12A—C18A1.515 (16)O42A—C48A1.498 (14)
C18A—H18A0.9600C48A—H48A0.9600
C18A—H18B0.9600C48A—H48B0.9600
C18A—H18C0.9600C48A—H48C0.9600
C21—C221.370 (13)C51—C521.354 (13)
C21—C261.419 (14)C51—C561.451 (14)
C22—C231.406 (14)C52—C531.342 (13)
C22—H220.9300C52—H520.9300
C23—C241.377 (15)C53—C541.424 (14)
C24—C251.344 (16)C54—C551.402 (15)
C24—H240.9300C54—H540.9300
C25—C261.329 (16)C55—C561.330 (14)
C25—H250.9300C55—H550.9300
C26—H260.9300C56—H560.9300
C21A—N22A1.303 (14)C51A—C56A1.308 (13)
C21A—C26A1.448 (17)C51A—N52A1.309 (13)
N22A—C23A1.302 (14)N52A—C53A1.401 (14)
C23A—C24A1.410 (16)C53A—C54A1.367 (15)
C23A—H23A0.9300C53A—H53A0.9300
C24A—C25A1.314 (18)C54A—C55A1.409 (15)
C24A—C27A1.481 (19)C54A—C57A1.500 (16)
C25A—C26A1.357 (18)C55A—C56A1.294 (13)
C25A—H25A0.9300C55A—H55A0.9300
C26A—H26A0.9300C56A—H56A0.9300
C27A—O21A1.160 (15)C57A—O51A1.195 (14)
C27A—O22A1.344 (17)C57A—O52A1.325 (14)
O22A—C28A1.423 (16)O52A—C58A1.513 (16)
C28A—H28A0.9600C58A—H58A0.9600
C28A—H28B0.9600C58A—H58B0.9600
C28A—H28C0.9600C58A—H58C0.9600
C31—C321.381 (14)C61—C661.342 (15)
C31—C361.403 (16)C61—C621.411 (14)
C32—C331.431 (14)C62—C631.324 (13)
C32—H320.9300C62—H620.9300
C33—C341.395 (15)C63—C641.423 (14)
C34—C351.336 (16)C64—C651.381 (16)
C34—H340.9300C64—H640.9300
C35—C361.369 (17)C65—C661.324 (16)
C35—H350.9300C65—H650.9300
C36—H360.9300C66—H660.9300
C31A—N32A1.291 (11)C61A—N62A1.283 (11)
C31A—C36A1.377 (13)C61A—C66A1.406 (13)
N32A—C33A1.383 (12)N62A—C63A1.341 (11)
C33A—C34A1.372 (13)C63A—C64A1.411 (13)
C33A—H33A0.9300C63A—H63A0.9300
C34A—C35A1.392 (14)C64A—C65A1.314 (14)
C34A—C37A1.504 (16)C64A—C67A1.527 (16)
C35A—C36A1.413 (15)C65A—C66A1.425 (14)
C35A—H35A0.9300C65A—H65A0.9300
C36A—H36A0.9300C66A—H66A0.9300
C37A—O31A1.201 (15)C67A—O61A1.249 (15)
C37A—O32A1.279 (15)C67A—O62A1.265 (16)
O32A—C38A1.433 (13)O62A—C68A1.449 (14)
C38A—H38A0.9600C68A—H68A0.9600
C38A—H38B0.9600C68A—H68B0.9600
C38A—H38C0.9600C68A—H68C0.9600
O1A—C1A—C13121.2 (10)O1B—C1B—N4118.1 (9)
O1A—C1A—N1120.9 (10)O1B—C1B—C43123.9 (8)
C13—C1A—N1117.8 (9)N4—C1B—C43118.0 (9)
C11A—N1—C2A120.5 (8)C2B—N4—C41A120.3 (8)
C11A—N1—C1A116.8 (8)C2B—N4—C1B118.6 (8)
C2A—N1—C1A116.6 (8)C41A—N4—C1B116.2 (8)
O2A—C2A—N1117.7 (9)O2B—C2B—N4120.3 (9)
O2A—C2A—C21121.4 (10)O2B—C2B—C51121.9 (9)
N1—C2A—C21120.2 (9)N4—C2B—C51117.5 (10)
O3A—C3A—N2123.0 (13)O3B—C3B—C53126.3 (12)
O3A—C3A—C23119.8 (11)O3B—C3B—N5117.6 (11)
N2—C3A—C23117.2 (12)C53—C3B—N5115.6 (11)
C3A—N2—C4A119.0 (11)C51A—N5—C3B115.8 (8)
C3A—N2—C21A119.0 (10)C51A—N5—C4B113.4 (9)
C4A—N2—C21A119.2 (9)C3B—N5—C4B126.4 (10)
O4A—C4A—N2117.4 (10)O4B—C4B—N5121.7 (10)
O4A—C4A—C31120.4 (11)O4B—C4B—C61126.9 (11)
N2—C4A—C31121.8 (10)N5—C4B—C61111.2 (11)
O5A—C5A—N3120.3 (9)O5B—C5B—N6119.7 (9)
O5A—C5A—C33121.9 (10)O5B—C5B—C63123.5 (10)
N3—C5A—C33117.8 (9)N6—C5B—C63116.8 (9)
C5A—N3—C31A124.5 (8)C5B—N6—C6B121.2 (8)
C5A—N3—C6A118.4 (8)C5B—N6—C61A124.7 (8)
C31A—N3—C6A114.6 (8)C6B—N6—C61A111.8 (8)
O6A—C6A—C11126.7 (9)O6B—C6B—N6119.0 (9)
O6A—C6A—N3119.7 (9)O6B—C6B—C41122.7 (8)
C11—C6A—N3113.5 (9)N6—C6B—C41118.0 (8)
C12—C11—C16118.1 (9)C46—C41—C42120.2 (9)
C12—C11—C6A126.0 (8)C46—C41—C6B117.7 (9)
C16—C11—C6A115.8 (9)C42—C41—C6B121.9 (8)
C11—C12—C13121.9 (8)C43—C42—C41119.9 (8)
C11—C12—H12119.0C43—C42—H42120.0
C13—C12—H12119.0C41—C42—H42120.0
C12—C13—C14119.9 (8)C42—C43—C44120.8 (9)
C12—C13—C1A120.8 (8)C42—C43—C1B121.0 (9)
C14—C13—C1A118.5 (9)C44—C43—C1B117.5 (9)
C15—C14—C13118.0 (9)C45—C44—C43117.4 (10)
C15—C14—H14121.0C45—C44—H44121.3
C13—C14—H14121.0C43—C44—H44121.3
C16—C15—C14121.4 (9)C46—C45—C44121.0 (10)
C16—C15—H15119.3C46—C45—H45119.5
C14—C15—H15119.3C44—C45—H45119.5
C15—C16—C11120.2 (9)C41—C46—C45120.6 (10)
C15—C16—H16119.9C41—C46—H46119.7
C11—C16—H16119.9C45—C46—H46119.7
N12A—C11A—N1120.8 (10)N42A—C41A—N4120.9 (9)
N12A—C11A—C16A121.0 (10)N42A—C41A—C46A120.5 (9)
N1—C11A—C16A118.2 (11)N4—C41A—C46A118.3 (10)
C11A—N12A—C13A120.7 (9)C43A—N42A—C41A119.9 (9)
N12A—C13A—C14A119.4 (10)N42A—C43A—C44A124.8 (10)
N12A—C13A—H13A120.3N42A—C43A—H43A117.6
C14A—C13A—H13A120.3C44A—C43A—H43A117.6
C15A—C14A—C13A119.6 (10)C45A—C44A—C43A114.4 (10)
C15A—C14A—C17A123.6 (11)C45A—C44A—C47A123.5 (10)
C13A—C14A—C17A116.6 (11)C43A—C44A—C47A122.1 (10)
C16A—C15A—C14A119.0 (11)C46A—C45A—C44A122.5 (10)
C16A—C15A—H15A120.5C46A—C45A—H45A118.7
C14A—C15A—H15A120.5C44A—C45A—H45A118.7
C15A—C16A—C11A119.7 (11)C45A—C46A—C41A117.4 (10)
C15A—C16A—H16A120.1C45A—C46A—H46A121.3
C11A—C16A—H16A120.1C41A—C46A—H46A121.3
O11A—C17A—O12A123.6 (13)O41A—C47A—O42A122.5 (12)
O11A—C17A—C14A122.8 (12)O41A—C47A—C44A124.1 (11)
O12A—C17A—C14A113.4 (12)O42A—C47A—C44A113.1 (12)
C17A—O12A—C18A115.4 (11)C47A—O42A—C48A117.3 (11)
O12A—C18A—H18A109.5O42A—C48A—H48A109.5
O12A—C18A—H18B109.5O42A—C48A—H48B109.5
H18A—C18A—H18B109.5H48A—C48A—H48B109.5
O12A—C18A—H18C109.5O42A—C48A—H48C109.5
H18A—C18A—H18C109.5H48A—C48A—H48C109.5
H18B—C18A—H18C109.5H48B—C48A—H48C109.5
C22—C21—C26121.1 (10)C52—C51—C56118.5 (10)
C22—C21—C2A120.1 (10)C52—C51—C2B124.9 (9)
C26—C21—C2A118.4 (9)C56—C51—C2B116.1 (9)
C21—C22—C23117.3 (9)C53—C52—C51123.6 (10)
C21—C22—H22121.4C53—C52—H52118.2
C23—C22—H22121.4C51—C52—H52118.2
C24—C23—C22119.1 (10)C52—C53—C3B122.1 (10)
C24—C23—C3A124.8 (11)C52—C53—C54117.9 (10)
C22—C23—C3A115.9 (10)C3B—C53—C54120.0 (10)
C25—C24—C23122.7 (11)C55—C54—C53119.8 (10)
C25—C24—H24118.7C55—C54—H54120.1
C23—C24—H24118.7C53—C54—H54120.1
C26—C25—C24119.6 (12)C56—C55—C54120.9 (11)
C26—C25—H25120.2C56—C55—H55119.5
C24—C25—H25120.2C54—C55—H55119.5
C25—C26—C21120.0 (10)C55—C56—C51119.3 (10)
C25—C26—H26120.0C55—C56—H56120.4
C21—C26—H26120.0C51—C56—H56120.4
N22A—C21A—N2117.0 (12)C56A—C51A—N52A126.0 (11)
N22A—C21A—C26A122.0 (13)C56A—C51A—N5116.7 (10)
N2—C21A—C26A121.0 (13)N52A—C51A—N5117.3 (10)
C23A—N22A—C21A117.1 (11)C51A—N52A—C53A116.3 (10)
N22A—C23A—C24A124.9 (12)C54A—C53A—N52A121.0 (11)
N22A—C23A—H23A117.6C54A—C53A—H53A119.5
C24A—C23A—H23A117.6N52A—C53A—H53A119.5
C25A—C24A—C23A117.4 (13)C53A—C54A—C55A115.2 (11)
C25A—C24A—C27A117.2 (14)C53A—C54A—C57A121.9 (12)
C23A—C24A—C27A125.3 (14)C55A—C54A—C57A122.8 (11)
C24A—C25A—C26A121.1 (14)C56A—C55A—C54A123.2 (11)
C24A—C25A—H25A119.4C56A—C55A—H55A118.4
C26A—C25A—H25A119.4C54A—C55A—H55A118.4
C25A—C26A—C21A117.2 (13)C55A—C56A—C51A118.2 (10)
C25A—C26A—H26A121.4C55A—C56A—H56A120.9
C21A—C26A—H26A121.4C51A—C56A—H56A120.9
O21A—C27A—O22A126.7 (16)O51A—C57A—O52A127.7 (13)
O21A—C27A—C24A124.6 (17)O51A—C57A—C54A121.4 (13)
O22A—C27A—C24A108.6 (14)O52A—C57A—C54A110.8 (12)
C27A—O22A—C28A115.7 (13)C57A—O52A—C58A113.1 (10)
O22A—C28A—H28A109.5O52A—C58A—H58A109.5
O22A—C28A—H28B109.5O52A—C58A—H58B109.5
H28A—C28A—H28B109.5H58A—C58A—H58B109.5
O22A—C28A—H28C109.5O52A—C58A—H58C109.5
H28A—C28A—H28C109.5H58A—C58A—H58C109.5
H28B—C28A—H28C109.5H58B—C58A—H58C109.5
C32—C31—C36119.2 (11)C66—C61—C62118.3 (10)
C32—C31—C4A119.6 (10)C66—C61—C4B120.2 (11)
C36—C31—C4A121.2 (11)C62—C61—C4B119.6 (10)
C31—C32—C33122.0 (10)C63—C62—C61121.0 (10)
C31—C32—H32119.0C63—C62—H62119.5
C33—C32—H32119.0C61—C62—H62119.5
C34—C33—C5A122.6 (11)C62—C63—C64119.1 (10)
C34—C33—C32115.2 (11)C62—C63—C5B123.0 (10)
C5A—C33—C32121.9 (10)C64—C63—C5B117.6 (10)
C35—C34—C33121.7 (12)C65—C64—C63118.5 (11)
C35—C34—H34119.2C65—C64—H64120.7
C33—C34—H34119.2C63—C64—H64120.7
C34—C35—C36123.2 (13)C66—C65—C64120.2 (12)
C34—C35—H35118.4C66—C65—H65119.9
C36—C35—H35118.4C64—C65—H65119.9
C35—C36—C31117.9 (12)C65—C66—C61122.5 (12)
C35—C36—H36121.0C65—C66—H66118.7
C31—C36—H36121.0C61—C66—H66118.7
N32A—C31A—C36A125.1 (10)N62A—C61A—C66A124.7 (9)
N32A—C31A—N3115.0 (8)N62A—C61A—N6116.0 (8)
C36A—C31A—N3119.9 (10)C66A—C61A—N6119.3 (9)
C31A—N32A—C33A117.3 (9)C61A—N62A—C63A120.5 (8)
C34A—C33A—N32A123.2 (10)N62A—C63A—C64A119.9 (10)
C34A—C33A—H33A118.4N62A—C63A—H63A120.0
N32A—C33A—H33A118.4C64A—C63A—H63A120.0
C33A—C34A—C35A117.5 (10)C65A—C64A—C63A118.7 (10)
C33A—C34A—C37A121.2 (12)C65A—C64A—C67A123.4 (11)
C35A—C34A—C37A121.3 (11)C63A—C64A—C67A117.9 (12)
C34A—C35A—C36A119.4 (10)C64A—C65A—C66A122.8 (10)
C34A—C35A—H35A120.3C64A—C65A—H65A118.6
C36A—C35A—H35A120.3C66A—C65A—H65A118.6
C31A—C36A—C35A117.3 (11)C61A—C66A—C65A113.3 (9)
C31A—C36A—H36A121.3C61A—C66A—H66A123.4
C35A—C36A—H36A121.3C65A—C66A—H66A123.4
O31A—C37A—O32A126.6 (12)O61A—C67A—O62A130.4 (12)
O31A—C37A—C34A119.8 (15)O61A—C67A—C64A114.7 (15)
O32A—C37A—C34A113.6 (13)O62A—C67A—C64A114.8 (11)
C37A—O32A—C38A115.3 (10)C67A—O62A—C68A117.3 (10)
O32A—C38A—H38A109.5O62A—C68A—H68A109.5
O32A—C38A—H38B109.5O62A—C68A—H68B109.5
H38A—C38A—H38B109.5H68A—C68A—H68B109.5
O32A—C38A—H38C109.5O62A—C68A—H68C109.5
H38A—C38A—H38C109.5H68A—C68A—H68C109.5
H38B—C38A—H38C109.5H68B—C68A—H68C109.5
O1A—C1A—N1—C11A127.5 (10)O1B—C1B—N4—C2B26.1 (13)
C13—C1A—N1—C11A54.9 (12)C43—C1B—N4—C2B152.4 (9)
O1A—C1A—N1—C2A25.2 (14)O1B—C1B—N4—C41A129.3 (10)
C13—C1A—N1—C2A152.3 (9)C43—C1B—N4—C41A52.2 (11)
C11A—N1—C2A—O2A14.3 (14)C41A—N4—C2B—O2B18.0 (14)
C1A—N1—C2A—O2A137.4 (9)C1B—N4—C2B—O2B136.3 (9)
C11A—N1—C2A—C21155.7 (9)C41A—N4—C2B—C51155.4 (9)
C1A—N1—C2A—C2152.6 (12)C1B—N4—C2B—C5150.2 (11)
O3A—C3A—N2—C4A17.4 (16)O3B—C3B—N5—C51A148.9 (10)
C23—C3A—N2—C4A164.8 (9)C53—C3B—N5—C51A37.7 (12)
O3A—C3A—N2—C21A143.5 (12)O3B—C3B—N5—C4B6.0 (15)
C23—C3A—N2—C21A34.3 (14)C53—C3B—N5—C4B167.4 (9)
C3A—N2—C4A—O4A143.1 (11)C51A—N5—C4B—O4B22.6 (17)
C21A—N2—C4A—O4A17.8 (16)C3B—N5—C4B—O4B132.8 (13)
C3A—N2—C4A—C3143.9 (15)C51A—N5—C4B—C61160.9 (9)
C21A—N2—C4A—C31155.3 (11)C3B—N5—C4B—C6143.7 (14)
O5A—C5A—N3—C31A11.6 (14)O5B—C5B—N6—C6B148.1 (9)
C33—C5A—N3—C31A169.3 (8)C63—C5B—N6—C6B32.7 (12)
O5A—C5A—N3—C6A149.3 (9)O5B—C5B—N6—C61A13.7 (14)
C33—C5A—N3—C6A29.8 (12)C63—C5B—N6—C61A165.5 (8)
C5A—N3—C6A—O6A44.0 (13)C5B—N6—C6B—O6B41.0 (13)
C31A—N3—C6A—O6A118.7 (10)C61A—N6—C6B—O6B122.9 (9)
C5A—N3—C6A—C11132.1 (8)C5B—N6—C6B—C41132.4 (9)
C31A—N3—C6A—C1165.2 (10)C61A—N6—C6B—C4163.6 (10)
O6A—C6A—C11—C12161.0 (10)O6B—C6B—C41—C4616.7 (14)
N3—C6A—C11—C1214.8 (12)N6—C6B—C41—C46170.1 (8)
O6A—C6A—C11—C1615.1 (14)O6B—C6B—C41—C42159.0 (9)
N3—C6A—C11—C16169.2 (8)N6—C6B—C41—C4214.2 (13)
C16—C11—C12—C133.8 (13)C46—C41—C42—C432.1 (13)
C6A—C11—C12—C13172.1 (8)C6B—C41—C42—C43173.5 (8)
C11—C12—C13—C143.7 (13)C41—C42—C43—C442.9 (13)
C11—C12—C13—C1A165.9 (8)C41—C42—C43—C1B167.3 (8)
O1A—C1A—C13—C12141.0 (10)O1B—C1B—C43—C42140.4 (10)
N1—C1A—C13—C1236.5 (13)N4—C1B—C43—C4238.0 (13)
O1A—C1A—C13—C1428.7 (14)O1B—C1B—C43—C4430.2 (15)
N1—C1A—C13—C14153.8 (8)N4—C1B—C43—C44151.4 (8)
C12—C13—C14—C152.1 (13)C42—C43—C44—C451.0 (14)
C1A—C13—C14—C15171.9 (9)C1B—C43—C44—C45169.6 (9)
C13—C14—C15—C167.8 (14)C43—C44—C45—C461.8 (14)
C14—C15—C16—C117.7 (15)C42—C41—C46—C450.6 (14)
C12—C11—C16—C151.8 (13)C6B—C41—C46—C45176.4 (9)
C6A—C11—C16—C15178.2 (9)C44—C45—C46—C412.6 (15)
C2A—N1—C11A—N12A123.7 (10)C2B—N4—C41A—N42A121.3 (10)
C1A—N1—C11A—N12A27.9 (12)C1B—N4—C41A—N42A33.6 (12)
C2A—N1—C11A—C16A55.0 (12)C2B—N4—C41A—C46A52.9 (12)
C1A—N1—C11A—C16A153.3 (9)C1B—N4—C41A—C46A152.2 (8)
N1—C11A—N12A—C13A175.0 (8)N4—C41A—N42A—C43A172.3 (8)
C16A—C11A—N12A—C13A3.7 (14)C46A—C41A—N42A—C43A1.7 (14)
C11A—N12A—C13A—C14A2.7 (14)C41A—N42A—C43A—C44A4.5 (14)
N12A—C13A—C14A—C15A5.0 (13)N42A—C43A—C44A—C45A6.8 (13)
N12A—C13A—C14A—C17A169.2 (8)N42A—C43A—C44A—C47A172.6 (9)
C13A—C14A—C15A—C16A0.7 (14)C43A—C44A—C45A—C46A2.9 (13)
C17A—C14A—C15A—C16A173.1 (9)C47A—C44A—C45A—C46A176.6 (9)
C14A—C15A—C16A—C11A5.5 (15)C44A—C45A—C46A—C41A2.5 (14)
N12A—C11A—C16A—C15A8.0 (15)N42A—C41A—C46A—C45A5.2 (14)
N1—C11A—C16A—C15A170.7 (9)N4—C41A—C46A—C45A169.0 (9)
C15A—C14A—C17A—O11A164.0 (11)C45A—C44A—C47A—O41A165.6 (11)
C13A—C14A—C17A—O11A22.0 (15)C43A—C44A—C47A—O41A15.0 (15)
C15A—C14A—C17A—O12A11.6 (13)C45A—C44A—C47A—O42A20.6 (13)
C13A—C14A—C17A—O12A162.4 (9)C43A—C44A—C47A—O42A158.8 (9)
O11A—C17A—O12A—C18A8.5 (16)O41A—C47A—O42A—C48A0.3 (15)
C14A—C17A—O12A—C18A175.9 (9)C44A—C47A—O42A—C48A173.6 (9)
O2A—C2A—C21—C22156.2 (9)O2B—C2B—C51—C52154.6 (10)
N1—C2A—C21—C2213.4 (13)N4—C2B—C51—C5218.8 (13)
O2A—C2A—C21—C2616.6 (14)O2B—C2B—C51—C5617.2 (13)
N1—C2A—C21—C26173.8 (9)N4—C2B—C51—C56169.4 (8)
C26—C21—C22—C230.7 (14)C56—C51—C52—C533.3 (14)
C2A—C21—C22—C23171.9 (9)C2B—C51—C52—C53168.3 (9)
C21—C22—C23—C242.1 (14)C51—C52—C53—C3B176.6 (10)
C21—C22—C23—C3A178.1 (9)C51—C52—C53—C541.9 (14)
O3A—C3A—C23—C2450.7 (16)O3B—C3B—C53—C52118.5 (13)
N2—C3A—C23—C24127.2 (12)N5—C3B—C53—C5254.3 (13)
O3A—C3A—C23—C22125.1 (12)O3B—C3B—C53—C5460.1 (15)
N2—C3A—C23—C2257.0 (13)N5—C3B—C53—C54127.2 (10)
C22—C23—C24—C255.7 (18)C52—C53—C54—C550.2 (14)
C3A—C23—C24—C25178.6 (12)C3B—C53—C54—C55178.4 (10)
C23—C24—C25—C266 (2)C53—C54—C55—C560.1 (16)
C24—C25—C26—C213.2 (19)C54—C55—C56—C511.5 (15)
C22—C21—C26—C250.2 (17)C52—C51—C56—C553.1 (14)
C2A—C21—C26—C25172.6 (11)C2B—C51—C56—C55169.3 (9)
C3A—N2—C21A—N22A49.2 (14)C3B—N5—C51A—C56A52.1 (12)
C4A—N2—C21A—N22A111.7 (12)C4B—N5—C51A—C56A106.0 (11)
C3A—N2—C21A—C26A128.9 (11)C3B—N5—C51A—N52A126.3 (10)
C4A—N2—C21A—C26A70.2 (13)C4B—N5—C51A—N52A75.6 (11)
N2—C21A—N22A—C23A178.0 (10)C56A—C51A—N52A—C53A0.6 (15)
C26A—C21A—N22A—C23A3.9 (16)N5—C51A—N52A—C53A177.6 (8)
C21A—N22A—C23A—C24A5.4 (18)C51A—N52A—C53A—C54A2.8 (16)
N22A—C23A—C24A—C25A4.3 (19)N52A—C53A—C54A—C55A3.5 (15)
N22A—C23A—C24A—C27A179.3 (12)N52A—C53A—C54A—C57A178.5 (10)
C23A—C24A—C25A—C26A1.5 (18)C53A—C54A—C55A—C56A2.2 (16)
C27A—C24A—C25A—C26A178.1 (11)C57A—C54A—C55A—C56A179.9 (10)
C24A—C25A—C26A—C21A0.2 (17)C54A—C55A—C56A—C51A0.1 (16)
N22A—C21A—C26A—C25A1.5 (16)N52A—C51A—C56A—C55A0.7 (16)
N2—C21A—C26A—C25A179.5 (10)N5—C51A—C56A—C55A178.9 (9)
C25A—C24A—C27A—O21A4 (2)C53A—C54A—C57A—O51A6.5 (18)
C23A—C24A—C27A—O21A172.5 (14)C55A—C54A—C57A—O51A175.7 (11)
C25A—C24A—C27A—O22A173.0 (11)C53A—C54A—C57A—O52A175.9 (10)
C23A—C24A—C27A—O22A10.6 (17)C55A—C54A—C57A—O52A1.9 (15)
O21A—C27A—O22A—C28A9 (2)O51A—C57A—O52A—C58A2.7 (19)
C24A—C27A—O22A—C28A174.7 (15)C54A—C57A—O52A—C58A179.9 (11)
O4A—C4A—C31—C32134.2 (12)O4B—C4B—C61—C6630 (2)
N2—C4A—C31—C3238.7 (16)N5—C4B—C61—C66146.4 (11)
O4A—C4A—C31—C3643.4 (17)O4B—C4B—C61—C62134.3 (14)
N2—C4A—C31—C36143.8 (12)N5—C4B—C61—C6249.5 (14)
C36—C31—C32—C331.2 (17)C66—C61—C62—C632.5 (17)
C4A—C31—C32—C33176.4 (10)C4B—C61—C62—C63166.9 (10)
O5A—C5A—C33—C3435.8 (15)C61—C62—C63—C642.1 (15)
N3—C5A—C33—C34143.2 (10)C61—C62—C63—C5B176.3 (10)
O5A—C5A—C33—C32137.4 (10)O5B—C5B—C63—C62136.1 (11)
N3—C5A—C33—C3243.6 (13)N6—C5B—C63—C6243.1 (13)
C31—C32—C33—C346.8 (15)O5B—C5B—C63—C6438.2 (14)
C31—C32—C33—C5A179.5 (10)N6—C5B—C63—C64142.7 (9)
C5A—C33—C34—C35175.8 (11)C62—C63—C64—C652.8 (16)
C32—C33—C34—C3510.6 (17)C5B—C63—C64—C65177.2 (11)
C33—C34—C35—C369 (2)C63—C64—C65—C661.4 (19)
C34—C35—C36—C313 (2)C64—C65—C66—C616 (2)
C32—C31—C36—C351.0 (18)C62—C61—C66—C657 (2)
C4A—C31—C36—C35178.6 (12)C4B—C61—C66—C65171.2 (13)
C5A—N3—C31A—N32A147.0 (9)C5B—N6—C61A—N62A144.4 (9)
C6A—N3—C31A—N32A14.5 (11)C6B—N6—C61A—N62A18.9 (10)
C5A—N3—C31A—C36A35.2 (13)C5B—N6—C61A—C66A35.0 (12)
C6A—N3—C31A—C36A163.3 (9)C6B—N6—C61A—C66A161.7 (8)
C36A—C31A—N32A—C33A0.6 (14)C66A—C61A—N62A—C63A0.5 (13)
N3—C31A—N32A—C33A177.1 (7)N6—C61A—N62A—C63A179.9 (7)
C31A—N32A—C33A—C34A5.5 (14)C61A—N62A—C63A—C64A2.1 (13)
N32A—C33A—C34A—C35A6.4 (14)N62A—C63A—C64A—C65A0.5 (14)
N32A—C33A—C34A—C37A176.3 (9)N62A—C63A—C64A—C67A179.1 (8)
C33A—C34A—C35A—C36A2.5 (14)C63A—C64A—C65A—C66A2.5 (15)
C37A—C34A—C35A—C36A179.8 (9)C67A—C64A—C65A—C66A178.0 (9)
N32A—C31A—C36A—C35A2.9 (15)N62A—C61A—C66A—C65A2.2 (13)
N3—C31A—C36A—C35A179.5 (8)N6—C61A—C66A—C65A177.1 (7)
C34A—C35A—C36A—C31A1.9 (14)C64A—C65A—C66A—C61A3.7 (14)
C33A—C34A—C37A—O31A174.1 (11)C65A—C64A—C67A—O61A10.9 (15)
C35A—C34A—C37A—O31A8.7 (17)C63A—C64A—C67A—O61A168.7 (9)
C33A—C34A—C37A—O32A7.0 (15)C65A—C64A—C67A—O62A172.1 (10)
C35A—C34A—C37A—O32A170.1 (10)C63A—C64A—C67A—O62A8.3 (13)
O31A—C37A—O32A—C38A5.3 (18)O61A—C67A—O62A—C68A3.2 (18)
C34A—C37A—O32A—C38A175.9 (8)C64A—C67A—O62A—C68A173.2 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C35A—H35A···O31Ai0.932.363.204 (13)150
C65A—H65A···O61Aii0.932.413.227 (14)146
C12—H12···N30.932.582.907 (12)101
C22—H22···N10.932.572.886 (14)100
C23A—H23A···O22A0.932.422.736 (17)100
C28A—H28A···O21A0.962.242.68 (2)107
C33A—H33A···O32A0.932.402.731 (14)101
C36A—H36A···O5A0.932.452.843 (13)105
C38A—H38A···O31A0.962.192.630 (17)107
C48A—H48A···O41A0.962.282.642 (16)101
C55—H55···O3A0.932.593.377 (14)143
C55A—H55A···O52A0.932.412.735 (14)100
C63A—H63A···O62A0.932.402.726 (13)100
C66A—H66A···O5B0.932.522.858 (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 formulaC60H40N8O16C45H30N6O12
Mr1129.00846.75
Crystal system, space groupMonoclinic, P21/nTriclinic, P1
Temperature (K)294294
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), 9087.273 (5), 83.350 (7), 89.825 (4)
V3)5335.31 (8)4697.4 (6)
Z44
Radiation typeCu KαCu Kα
µ (mm1)0.880.75
Crystal size (mm)0.58 × 0.06 × 0.050.60 × 0.08 × 0.02
Data collection
DiffractometerXcalibur, Sapphire3, Gemini Ultra
diffractometer
Xcalibur, Sapphire3, Gemini Ultra
diffractometer
Absorption correctionAnalytical
(ABSFAC, Clark and Reid, 1998)
Analytical
(ABSFAC, Clark and Reid, 1998)
Tmin, Tmax0.631, 0.9580.663, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
31765, 8619, 6947 16648, 10048, 4137
Rint0.0340.083
θmax (°)63.351.4
(sin θ/λ)max1)0.5790.507
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.120, 1.03 0.121, 0.352, 0.91
No. of reflections861910048
No. of parameters7621141
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.170.47, 0.35

Computer programs: CrysAlis PRO, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995), PLATON (Spek, 2009), SHELXL97.

Hydrogen-bond geometry (Å, º) for (EsIO4_I_12-001) top
D—H···AD—HH···AD···AD—H···A
C4A—H4A2···O5i0.962.563.491 (4)165
C6A—H6A3···O3ii0.962.583.461 (4)153
C26A—H26A···O5Aii0.932.423.333 (3)167
C15A—H15A···O4iii0.932.383.133 (3)138
C35A—H35A···O7iv0.932.573.107 (3)117
C36—H36···O6v0.932.483.400 (2)171
Symmetry codes: (i) x1/2, 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) x1, y, z.
Hydrogen-bond geometry (Å, º) for (EsIO3_II_12-015_Squeeze) top
D—H···AD—HH···AD···AD—H···A
C35A—H35A···O31Ai0.932.363.204 (13)150
C65A—H65A···O61Aii0.932.413.227 (14)146
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+2, y, z.
 

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