Carboxylated Pillar[6]arene Emulates Pillar[5]arene in the Host–Guest Crystal Complexes and Shows Conformational Flexibility in the Solution/Gas Phase

Supporting Information

Carboxylated Pillar[6]arene Emulates Pillar[5]arene in the Host- Guest Crystal Complexes and Shows Conformational Flexibility in the Solution/Gas Phase

Helena Butkiewicz,

Sandra Kosiorek,

Volodymyr Sashuk,

Magdalena M. Zimnicka,

* Oksana Danylyuk

*

a

Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

b

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland

Carboxylic acid substituted pillar[6]arene (CPA6) was synthesized according to the literature procedure

and used in the neutral carboxylic form. Pentamidine diisethionate and dimethyl viologen dichloride were purchased from Sigma-Aldrich.

Crystallization:

dMV@CPA6 host-guest complex: 0.6 mg of CPA6 and 3.8 mg of MgCl

were dissolved in 1 ml of a 1:1 water-ethanol mixture under gentle heating. 0.8 mg of dimethyl viologen dichloride dMV was dissolved in 0.2 ml of water. The crystals were obtained via slow liquid-liquid diffusion method, the solutions of host and guest in a narrow test tube were additionally separated by a layer of water-ethanol mixture to slow down nucleation. Red prismatic crystals appeared after 2 weeks.

PTM@CPA6 host-guest complex: 0.5 mg of CPA6 were dissolved in 0.5 ml of a 1:1 water-ethanol mixture under gentle heating. 1 mg of pentamidine diisethionate PTM was dissolved in 0.5 ml of water-ethanol mixture. The crystals were obtained via slow liquid-liquid diffusion method, the solutions of host and guest in a narrow test tube were additionally separated by a layer of n-butanol to slow down nucleation. The colourless plate-like crystals appeared after 2 months.

Photomicrographs of crystal morphology

Figure S1 Photomicrographs of crystals of host-guest complexes (left) dMV@CPA6 and (right) PTM@CPA6

Single Crystal X-ray Crystallography: The crystals were embedded in the inert perfluoropolyalkylether

(viscosity 1800cSt; ABCR GmbH) and mounted using Hampton Research Cryoloops. The crystals were flash

cooled to 100.0(1) K in a nitrogen gas stream and kept at this temperature during the experiments. The X-

ray data were collected on a SuperNova Agilent diffractometer using CuKα radiation (λ = 1.54184 Å). The

data were processed with CrysAlisPro.

Structures were solved by direct methods and refined using SHELXL

under WinGX.

The figures were prepared using Chimera.

Crystal data for dMV@CPA6 host-guest complex: 0.5(C

H

O

)·0.5(C

H

N

)·2.75(H

O), Mr = 856.2, red prisms, orthorhombic, space group Pbcn, a = 13.2412(4), b = 24.8061(14), c = 24.1666(9) Å, V = 7937.8(6) Å

, Z = 8, ρ

= 1.43 g·cm

, μ(CuKα) = 1.01 mm

, θ

= 68.3ᵒ, 24395 reflections measured, 7077 unique, 856 parameters, R = 0.127, wR = 0.325 (R = 0.202, wR = 0.396 for all data). GooF = 1.10. CCDC 2211394.

Crystal data for PTM@CPA6 host-guest complex: (C

H

O

)·2(C

H

N

O

)·(C

H

OH)·9.75(H

O), Mr = 2331.7, colorless plates, triclinic, space group P-1, a =14.9786(6), b =17.5913(6), c = 22.6900(12) Å, α = 88.572(4), β = 82.538(4), γ = 76.769(3)ᵒ, V =5770.6(4) Å

, Z = 2, ρ

= 1.34 g·cm

, μ(CuKα) = 0.92 mm

, θ

= 61.0ᵒ, 33191 reflections measured, 17226 unique, 1547 parameters, R = 0.104, wR = 0.259 (R = 0.173, wR

= 0.315 for all data). GooF = 1.11. CCDC 2211396.

IM-MS Measurements:

Ion mobility mass spectrometry (IM-MS) measurements were performed on a commercially available from Waters quadrupole traveling-wave ion mobility time-of-flight spectrometer (Synapt G2-S HDMS). A mixture of CPA6 (c = 0.016 mM) and dMV or PTM (c = 0.016) in MeOH/H

O (1:1) was infused through a standard electrospray ion source into the instrument at a flow rate of 10 μL/min. The samples were analyzed in negative ion mode with a capillary voltage at 3.5 kV and source temperature at 303 K. An ion mobility pressure of 3.4 mbar of nitrogen was used. Three sets of parameters, containing variable values of traveling wave velocity (WV) and pulse height (WH), were applied to determine the standard deviation values for the T-wave determined CCS values. All additional experimental details and parameters are given in the Table S1.

The uncertainties of the determined CCS values associated with different drift tube conditions were estimated at > 90% level of confidence.

Table S1. TWIMS experimental conditions.

Parameter Value

Mass Range

Source Temperature (°C)

250- 1500/2000 Da 30

Sampling Cone 40

Source Offset 40

Desolvation Temperature (°C) 80

Cone Gas Flow (L/Hr) 72

Desolvation Gas Flow (L/Hr) 600

Nebuliser Gas Flow (Bar) 2.5

HeliumCellGasFlow 180

IMS Gas Flow (mL/min) 80

IMS Wave Velocity (m/s) - WV 450, 500, 600 IMS Wave Height (V) - WH 30, 35, 34

CCS Calibration and Data Processing:

Experimental arrival time distributions (ATDs) for poly-dl-alanine reference anions and examined ions corresponding to doubly charged complexes of CPA6 with dMV and PTM were extracted manually from MassLynx software. The resulting ATDs were next fitted using a 3-parameter Gaussian function using SigmaPlot 12.0 to determine their mean values (Table S2). The improved calibration approach using IMSCal software package (available from imscal.on-demand.waters.com) was applied in order to convert the arrival time of examined ions to their CCS values.

The reference CCS values for singly and doubly negatively charged ions of the poly-dl-alanine

were used in the calibration procedure.

Table S2. Experimental mean arrival times (ATs) of CPA6 complexes with dMV and PTM, and reference ions

reported for different IM conditions.

Ion m/z

Exp. 1 Exp. 2 Exp. 3 Exp. 4 Exp. 5

WV/WH = 450/30 600/34 500/35 600/34 450/30 AT [ms]

[CPA6 + dMV - 4H]

805.0 3.8973 4.1869 3.3533

[CPA6 + PTM - 4H]

883.0 3.7879 4.8098 4.451

[CPA6 + 2PTM - 6H]

1053.1 4.6058 5.8477 5.4188

Poly-dl-alanine (z = -1)

301.0 2.9643 3.1428 2.557 3.1508 2.9782

372.1 3.4985 3.7301 3.0207 3.738 3.511

443.1 4.1121 4.3669 3.5156 4.372 4.124

514.1 4.7503 5.0268 4.0422 5.0295 4.7595

585.1 5.3851 5.6826 4.559 5.6804 5.3875

656.1 6.1281 6.4507 5.1625 6.448 6.1286

727.2 6.8738 7.2221 5.7667 7.2217 6.8705

798.2 7.6288 8.0129 6.3877 8.011 7.6222

869.2 8.3378 8.76 6.974 8.7534 8.328

940.2 9.1633 9.6245 7.6549 9.615 9.1543

1011.3 9.9921 10.4956 8.3377 10.4825 9.983 1082.3 10.816 11.3627 9.0232 11.3449 10.8082 1153.3 11.6384 12.2272 9.7062 12.2087 11.6313 1224.3 12.4975 13.1248 10.4161 13.1047 12.4891

1295.3 13.3597 11.1312

Poly-dl-alanine (z = -2)

434.1 2.9868 3.188 2.6095 3.1989 3.0076

469.6 3.204 3.4264 2.8118 3.439 3.2172

505.1 3.3771 3.6456 2.9822 3.6541 3.3902

540.6 3.5904 3.8711 3.1332 3.8808 3.5998

576.1 3.7976 4.0842 3.3038 4.0914 3.8082

611.6 4.0148 4.3086 3.487 4.3157 4.0231

647.1 4.2505 4.5419 3.6729 4.5474 4.2538

682.7 4.4717 4.7716 3.8486 4.7737 4.4727

718.4 4.7224 5.0257 4.0436 5.025 4.7206

753.7 4.9787 5.2854 4.2425 5.2799 4.9722

789.2 5.2381 5.5496 4.4492 5.5431 5.2275

824.7 5.5078 5.8289 4.6614 5.8201 5.4941

860.2 5.7772 6.1055 4.8769 6.0963 5.7627

895.7 6.0545 6.3975 5.1012 6.3883 6.0381

931.2 6.344 6.698 5.3342 6.6909 6.327

966.7 6.6197 6.99 5.5649 6.9844 6.6081

1002.2 6.9362 7.3241 5.8248 7.3195 6.9236

Theoretical Calculations:

The initial structures of CPA6-dMV and CPA6-PTM complexes were extracted from the crystallographic data

described in this manuscript. Based on the initial complex structures, various substructures corresponding to

the doubly negatively charged complexes were generated. These substructures varied in position of

carboxylate anions on both of the CPA6 rims. Two negative charges on each rim were solely considered

because only this arrangement enables effective solvation of the positive charge carried by dMV and PTM.

The substructures were subjected to the energy minimization followed by the Monte Carlo conformational search in MMFF force field using Spartan 18 molecular modelling package.

It is worth mentioning that the direct crystal structures of the complexes, particularly CPA6-dMV, do not represent DFT minima. The conformers were fully optimized at PM7 semiempirical quantum levels of theory using the semiempirical molecular orbital package MOPAC2012.

The conformers within the energy window of 20 kcal/mol were selected for DFT computations.

Final optimization and thermal analysis (1 atm, 298.15 K) using DFT/B3LYP hybrid functional and 6-31++G(d,p) basis set supplemented with D3 empirical dispersion correction were performed using Gaussian 16

A quasi- rigid rotor-harmonic oscillator approximation (RRHO) was used to account for low-frequency vibration modes (ν < 100 cm

) and to obtain a correct entropy values using GoodVibes program.

The conformers were ranked according to their Gibbs free energies. The xyz coordinates (Table S3) along with the B3LYP- D3/6-31++G(d,p) thermochemical properties (Table S4) of the most stable conformers (within the Gibbs free energy range of 20 kJ/mol) are provided.

The theoretical collision cross section values (

CCS

) of complexes were calculated for the most stable and dominant conformers according to Boltzmann distribution. The collision cross sections of the crystal structures were calculated for fully protonated CPA6 for simplicity, bearing in mind that they change only slightly compared to the deprotonated forms. The trajectory method (TM) implemented in MobCal-MPI was used to calculate CCS values of the optimized CPA6 complexes. In the CCS calculations the electrostatic potential (ESP) derived atomic charges was used.

Table S3. The xyz coordinates of CPA6 complexes with dMV and PTM (doubly charged).

[CPA6 + dMV -4H]^2- Conformer 1 [CPA6 + dMV -4H]^2- Conformer 2 [CPA6 + dMV -4H]^2- Conformer 3

C 9.812806 13.012192 5.087149 C 8.2784 -1.248611 6.789123 C 8.268712 -1.220033 6.770622 O 9.003713 12.58515 5.941212 O 7.948412 -1.806074 5.718181 O 7.938448 -1.769342 5.695637 O 9.92787 12.614245 3.888188 O 7.779338 -0.189078 7.275775 O 7.768282 -0.164978 7.26607 O 17.072168 5.280236 6.739612 O 14.978913 5.836502 2.016815 O 14.870997 5.892633 2.187658 O 15.385928 4.008557 5.935966 O 12.923884 6.506321 1.352738 O 12.921508 6.599475 1.289454 C 16.455141 13.425474 -0.459575 C 11.428573 4.521205 12.447727 C 11.460858 4.509164 12.4313 H 17.546626 13.370626 -0.49729 H 12.361826 5.004602 12.749659 H 12.394901 4.995931 12.725189 O 12.117395 12.525579 1.219401 O 8.397775 2.38357 9.49078 O 8.402104 2.394323 9.49354 O 11.018892 14.246967 2.205223 O 8.026817 0.171594 9.823673 O 8.032385 0.180349 9.814809 C 11.898167 13.713815 1.367515 C 8.354383 1.398996 10.205176 C 8.364245 1.404811 10.201607 O 17.238348 12.650391 4.391428 O 14.385836 2.388046 9.06259 O 14.412652 2.358728 9.053979 O 13.978349 14.459563 0.286123 O 9.694451 2.383401 12.018351 O 9.720612 2.375081 12.010219 C 12.63353 14.799125 0.57302 C 8.683206 1.44351 11.70175 C 8.704421 1.439825 11.695892 H 12.562469 15.753704 1.109505 H 8.945557 0.43521 12.046228 H 8.96605 0.428932 12.033144 H 12.137073 14.8814 -0.39685 H 7.785987 1.790629 12.219791 H 7.811852 1.786627 12.222124 C 14.956141 14.128837 5.151125 C 12.872513 0.004311 9.02256 C 12.880451 -0.012218 9.001681 H 15.873313 14.321072 5.715926 H 13.959887 -0.107527 9.071129 H 13.966957 -0.132602 9.048041 H 14.333049 15.025473 5.206216 H 12.422911 -0.887171 9.467914 H 12.424306 -0.903105 9.441542 C 15.318434 13.876469 3.702368 C 12.469616 1.21258 9.842339 C 12.486946 1.194324 9.828291 C 16.488645 13.184539 3.359413 C 13.274761 2.359728 9.88503 C 13.299291 2.336085 9.873808 C 16.856478 13.064374 2.013883 C 12.940665 3.411927 10.746281 C 12.969354 3.390508 10.73377 H 17.789715 12.591159 1.732662 H 13.587566 4.275184 10.84694 H 13.619334 4.251782 10.832306 C 16.029684 13.534298 0.99218 C 11.761018 3.390764 11.492303 C 11.789434 3.375116 11.479208 C 14.797831 14.110587 1.336083 C 10.891717 2.300014 11.343676 C 10.915608 2.287609 11.331989

C 14.478304 14.322961 2.679121 C 11.275871 1.203501 10.568197 C 11.293011 1.190556 10.554142 H 13.548175 14.799392 2.966884 H 10.637903 0.332549 10.471257 H 10.649516 0.323966 10.454789 C 18.372323 10.56153 5.164434 C 15.607313 3.797668 7.398334 C 15.627523 3.755148 7.374397 O 17.960768 10.77238 6.336536 O 15.981 4.979508 7.133898 O 15.973218 4.937479 7.077154 O 19.054117 9.561901 4.788097 O 15.792809 2.783877 6.674763 O 15.842143 2.728213 6.67654 C 18.021864 11.522677 4.027063 C 14.825454 3.691839 8.709466 C 14.846291 3.660739 8.6863 H 18.95602 11.819818 3.539191 H 15.433609 4.141901 9.500943 H 15.453285 4.121931 9.472363 H 17.465917 10.916322 3.301437 H 13.952952 4.342726 8.57359 H 13.970635 4.305968 8.544779 C 12.129956 4.590778 5.352505 C 9.836054 5.248393 1.150915 C 9.833206 5.286408 1.153091 H 12.927508 3.981393 5.77681 H 10.695037 5.713015 0.667819 H 10.691833 5.754304 0.672139 O 13.631385 5.090968 7.703076 O 12.296501 4.035533 0.455529 O 12.305808 4.084257 0.468852 O 10.793762 9.390734 5.636444 O 9.135694 1.279535 4.092513 O 9.134562 1.304519 4.078435 C 12.975926 6.176191 7.135719 C 11.534786 3.391175 1.421784 C 11.537077 3.434193 1.425754 C 11.454856 7.045423 5.480964 C 9.477828 3.2308 2.66677 C 9.475507 3.26315 2.661722 H 10.854405 6.908801 4.589006 H 8.518093 3.641626 2.958655 H 8.513879 3.670788 2.951458 O 16.523176 7.939351 9.482013 O 15.87272 2.146686 2.247666 O 15.889145 2.169165 2.240773 C 12.231031 8.483318 7.281786 C 11.115975 1.439177 2.805348 C 11.116427 1.47373 2.796423 O 15.013895 9.815745 7.552021 O 13.763512 1.471022 4.394028 O 13.776022 1.48302 4.383028 C 12.995454 7.422716 7.763502 C 11.939277 2.161328 1.94336 C 11.941547 2.202057 1.941935 H 13.607564 7.570812 8.647019 H 12.905864 1.751318 1.669932 H 12.909991 1.795963 1.669122 O 17.844988 8.734632 7.863876 O 16.281464 3.162601 4.196333 O 16.328056 3.1375 4.20741 C 12.198036 5.969026 5.985743 C 10.292553 3.941752 1.774755 C 10.291836 3.979726 1.775341 C 11.462115 8.28256 6.123627 C 9.877171 1.992419 3.167408 C 9.875785 2.0236 3.15852 C 15.020102 5.227252 7.970165 C 13.658885 4.301137 0.75183 C 13.658867 4.370121 0.794588 H 15.249605 4.536949 8.790412 H 14.188159 4.341223 -0.207251 H 14.203066 4.428196 -0.155406 H 15.309125 6.22794 8.303318 H 14.142853 3.522155 1.348275 H 14.142073 3.593055 1.393461 C 9.424808 9.262459 5.212853 C 7.730464 1.074295 3.862161 C 7.726214 1.112167 3.855755 H 9.266654 8.382545 4.590256 H 7.225766 1.99042 3.556755 H 7.226217 2.033625 3.559256 H 9.228227 10.171108 4.637688 H 7.340702 0.7319 4.824443 H 7.339684 0.766804 4.818279 C 12.204997 9.816773 7.995676 C 11.528443 0.07972 3.326029 C 11.528445 0.111221 3.308619 H 11.1641 10.114973 8.156726 H 10.71557 -0.631822 3.149317 H 10.714781 -0.598595 3.12861 H 12.674285 9.69512 8.977707 H 12.400739 -0.26067 2.757967 H 12.399838 -0.22646 2.737622 C 15.932481 4.854416 6.803689 C 13.915718 5.63127 1.456368 C 13.873911 5.6997 1.51464 O 12.139408 13.941985 5.226303 O 10.442409 -1.049385 8.042222 O 10.437405 -1.032921 8.019402 C 16.818722 8.825017 8.697559 C 15.812015 2.162129 3.465629 C 15.834562 2.161448 3.458991 C 14.298201 10.90623 7.069544 C 12.987619 0.743764 5.289342 C 12.995453 0.753799 5.273651 C 15.963022 10.092266 8.5867 C 15.115293 1.031449 4.230158 C 15.121056 1.02794 4.204985 H 15.448986 10.252707 9.541885 H 15.148558 0.121562 3.619173 H 15.1389 0.12932 3.576886 H 16.573325 10.964104 8.333992 H 15.589458 0.85451 5.199825 H 15.595607 0.825333 5.169456 C 12.818405 12.947594 5.894575 C 11.282674 -0.511898 7.09259 C 11.281656 -0.498464 7.071621 C 12.911178 10.913442 7.22882 C 11.856225 0.085927 4.803282 C 11.857756 0.108311 4.78539 C 8.517595 9.185498 6.446558 C 7.544738 0.003177 2.780854 C 7.525845 0.049084 2.769204 C 14.947097 11.934325 6.389794 C 13.300536 0.726001 6.646515 C 13.310842 0.722561 6.630016 H 16.02695 11.91225 6.29676 H 14.192915 1.234364 6.993849 H 14.210281 1.217144 6.978904 C 12.182099 11.942626 6.62737 C 11.007497 -0.535337 5.722919 C 11.004359 -0.510803 5.702379 H 11.107011 11.921492 6.728737 H 10.118393 -1.014502 5.340426 H 10.110233 -0.979333 5.318335 C 14.224857 12.981615 5.81724 C 12.472249 0.078348 7.563486 C 12.478345 0.076031 7.543934 O 8.061726 8.132889 6.846596 O 7.269846 0.287578 1.632271 O 7.245333 0.342327 1.624195

C 10.763795 14.147655 5.550118 C 9.411268 -1.932578 7.599524 C 9.402169 -1.910523 7.57478 H 10.492092 15.066725 5.02214 H 8.984105 -2.339706 8.520955 H 8.976126 -2.320819 8.49533 H 10.636867 14.290243 6.629166 H 9.829981 -2.745752 6.995945 H 9.81696 -2.721845 6.966089 O 8.311582 10.334925 7.096983 O 7.770236 -1.259138 3.159061 O 7.744797 -1.216845 3.138759 C 17.287754 5.650173 -0.930821 C 11.431099 10.446549 7.320086 C 11.419343 10.447906 7.322188 O 17.207675 6.618156 -0.187837 O 11.785545 9.299963 7.552751 O 11.77125 9.296429 7.535833 O 17.621051 4.426435 -0.596836 O 11.804156 11.19625 6.309803 O 11.786515 11.210647 6.320362 O 8.24711 6.234735 0.92149 O 4.457747 5.353263 4.032837 O 4.434935 5.37331 4.021754 O 9.337559 7.316503 2.578124 O 6.272063 4.008064 4.06961 O 6.253729 4.034255 4.074029 H 16.145389 14.332059 -0.988081 H 10.962067 4.101006 13.343737 H 11.000557 4.092597 13.332283 O 19.663538 10.886166 1.449427 O 14.991804 6.347514 10.353239 O 15.004205 6.324464 10.30436 O 18.826599 8.968395 2.310505 O 14.538879 6.818247 8.186702 O 14.549672 6.78105 8.135315 C 18.937705 9.912537 1.378487 C 14.256905 6.782616 9.486826 C 14.266898 6.751153 9.435995 O 13.054063 11.440815 -3.414268 O 6.907292 6.38365 11.873893 O 6.932023 6.358064 11.878414 O 17.628229 10.901776 -0.336417 O 12.352876 6.640832 10.89589 O 12.370464 6.621415 10.858279 C 17.998191 9.642236 0.203767 C 12.856954 7.329283 9.761752 C 12.863628 7.291825 9.708318 H 17.125739 9.083208 0.551714 H 12.223596 7.175019 8.884849 H 12.22658 7.115606 8.837738 H 18.503885 9.004887 -0.535575 H 12.908846 8.415357 9.924974 H 12.90753 8.381315 9.848431 C 14.341959 8.851106 -3.468312 C 7.841644 8.690128 10.394372 C 7.85199 8.667283 10.398826 H 13.524324 9.210493 -4.096517 H 6.847903 8.516821 10.812609 H 6.861224 8.488489 10.821604 H 15.153329 8.543424 -4.136374 H 8.21178 9.63111 10.814952 H 8.221816 9.606155 10.82432 C 14.838841 10.009262 -2.61512 C 8.760034 7.566552 10.853604 C 8.776175 7.543586 10.845438 C 14.198683 11.25472 -2.645345 C 8.265671 6.482002 11.58938 C 8.288582 6.459271 11.586017 C 14.711347 12.344374 -1.943727 C 9.120939 5.5008 12.088377 C 9.149136 5.481684 12.082173 H 14.164721 13.278623 -1.977924 H 8.685455 4.667305 12.625568 H 8.719439 4.649258 12.625542 C 15.873406 12.22973 -1.187005 C 10.493661 5.565639 11.871093 C 10.520307 5.548655 11.854984 C 16.491027 10.965683 -1.107513 C 10.991508 6.627278 11.089829 C 11.010488 6.60681 11.064105 C 15.984014 9.87457 -1.814099 C 10.13871 7.613398 10.592838 C 10.152317 7.590467 10.571268 H 16.473709 8.909665 -1.759441 H 10.531398 8.433645 10.004041 H 10.539691 8.408809 9.976249 C 11.076372 12.143108 -2.097509 C 5.874621 4.30807 10.9966 C 5.879157 4.293692 11.002085 O 9.909687 11.737038 -1.577065 O 5.082483 3.801527 10.041589 O 5.077425 3.794957 10.050629 O 11.454602 13.292404 -2.025364 O 6.324058 3.630006 11.895315 O 6.326581 3.610764 11.897969 C 11.857042 11.020038 -2.787089 C 6.135503 5.809103 10.836023 C 6.15344 5.792011 10.840817 H 12.051087 10.249769 -2.033588 H 6.61022 5.952873 9.860068 H 6.628324 5.931472 9.864238 H 11.212114 10.564711 -3.544873 H 5.171978 6.326135 10.797589 H 5.194386 6.317625 10.803229 H 11.176287 4.131042 5.636036 H 9.10272 5.017195 0.36997 H 9.101849 5.054281 0.370493 O 9.905902 4.800441 3.676064 O 7.102614 5.282981 1.715327 O 7.099045 5.305992 1.72259 O 14.837298 4.083275 1.22873 O 10.218449 9.185859 4.141332 O 10.197338 9.227619 4.139937 C 11.109816 4.649393 3.021475 C 7.836846 6.255512 2.360381 C 7.82954 6.282361 2.365866 C 13.491195 4.414026 3.229907 C 10.009586 7.204753 2.743074 C 9.997929 7.24437 2.743066 H 14.38094 4.385551 3.843267 H 11.08009 7.187176 2.596435 H 11.068291 7.233707 2.591822 O 8.77306 8.293471 -0.394454 O 4.466604 4.973239 6.499934 O 4.415 4.980173 6.48936 C 12.474328 4.338327 1.029695 C 8.065432 8.227034 3.770105 C 8.050152 8.254423 3.775898 O 10.791793 6.210578 -1.172895 O 5.65768 7.676795 6.028327 O 5.652162 7.67656 6.036808 C 11.230808 4.553402 1.634226 C 7.276217 7.226333 3.192078 C 7.265326 7.249594 3.199213 H 10.367966 4.637302 0.985421 H 6.215689 7.237732 3.410443 H 6.20536 7.254703 3.420457 O 9.663633 9.160819 -2.264017 O 4.336911 5.89166 8.543697 O 4.350121 5.885 8.543004 C 12.24646 4.56577 3.843638 C 9.219611 6.242612 2.111281 C 9.212042 6.277202 2.11386

C 13.613322 4.281894 1.844995 C 9.449335 8.198821 3.547915 C 9.433458 8.235096 3.549341 C 8.746736 5.004684 2.894238 C 5.730351 5.169171 2.032294 C 5.724871 5.193744 2.032112 H 7.92068 5.068527 3.608723 H 5.350378 4.362362 1.398577 H 5.347585 4.38758 1.395972 H 8.557192 4.168296 2.210131 H 5.175741 6.087691 1.803801 H 5.17288 6.113086 1.800644 C 15.731336 3.122942 1.820353 C 11.221493 9.826193 3.331288 C 11.194427 9.871748 3.325799 H 16.131326 2.532849 0.989356 H 11.133334 10.898383 3.534359 H 11.104697 10.943302 3.531892 H 15.188655 2.472631 2.512858 H 11.037026 9.630529 2.270718 H 11.004515 9.678241 2.265868 C 12.564387 4.141695 -0.468561 C 7.41776 9.326983 4.583868 C 7.398791 9.347226 4.596381 H 13.274394 3.334665 -0.674557 H 7.890334 10.279458 4.324155 H 7.865664 10.30356 4.340755 H 11.583208 3.832539 -0.840663 H 6.360425 9.388472 4.310002 H 6.340332 9.404331 4.325969 C 8.808417 6.320542 2.10789 C 5.512331 4.777055 3.499384 C 5.49667 4.800858 3.49751 O 16.085958 6.793501 -2.745729 O 9.582291 10.322185 8.934843 O 9.579672 10.311955 8.947412 C 9.358534 8.201431 -1.514826 C 4.395126 5.960037 7.292276 C 4.378711 5.961449 7.290828 C 12.102187 6.384508 -1.578336 C 6.624689 8.316554 6.780604 C 6.619191 8.317447 6.788904 C 9.74801 6.777429 -1.978907 C 4.40239 7.368142 6.650751 C 4.394573 7.373933 6.658834 H 8.889112 6.114895 -1.836545 H 3.671958 7.385558 5.836373 H 3.662873 7.402429 5.845959 H 10.038697 6.791996 -3.033962 H 4.144965 8.123444 7.399891 H 4.145052 8.126425 7.4134 C 14.782653 6.628847 -2.320187 C 8.634709 9.656605 8.181658 C 8.630295 9.653203 8.191414 C 13.008949 5.376536 -1.221412 C 7.526849 9.129635 6.079887 C 7.514098 9.140581 6.090769 C 16.909474 3.801118 2.559147 C 12.651426 9.364305 3.701687 C 12.62749 9.415177 3.688853 C 12.539505 7.49346 -2.308215 C 6.730465 8.189062 8.168668 C 6.731521 8.178694 8.175245 H 11.823538 8.253242 -2.595101 H 6.014428 7.574892 8.699921 H 6.020567 7.556393 8.703844 C 14.346813 5.519471 -1.595226 C 8.529294 9.785812 6.796592 C 8.51749 9.795125 6.808196 H 15.03131 4.739276 -1.289278 H 9.22577 10.389743 6.230074 H 9.209089 10.406827 6.243985 C 13.87787 7.638353 -2.685132 C 7.732735 8.84604 8.889303 C 7.734219 8.83389 8.896149 O 16.859584 3.922251 3.804488 O 13.200612 8.470404 3.020427 O 13.187182 8.544736 2.983686 C 17.008385 5.770527 -2.436147 C 10.465157 11.189114 8.254809 C 10.462877 11.182546 8.272878 H 17.941091 6.051845 -2.935494 H 11.055525 11.681706 9.034091 H 11.059904 11.662933 9.054688 H 16.687242 4.797841 -2.828973 H 9.927321 11.961104 7.690649 H 9.925215 11.96379 7.72137 O 17.878841 4.215124 1.849677 O 13.197257 9.921031 4.707684 O 13.167047 9.949981 4.707345 C 18.637414 6.543325 4.505599 C 6.572965 2.70589 7.074074 C 6.540639 2.73213 7.090083 H 18.97259 7.06399 5.398309 H 6.368641 2.982607 8.108815 H 6.360107 2.983168 8.135797 H 19.321818 6.740376 3.681918 H 6.674405 1.626227 7.000189 H 6.633816 1.653715 6.988342 H 18.513826 5.474215 4.674483 H 5.798649 3.089703 6.416394 H 5.754718 3.13671 6.459157 C 16.897886 6.935949 2.85192 C 8.996985 2.602338 6.716773 C 8.959868 2.627969 6.719452 N 17.314361 7.078682 4.12604 N 7.858471 3.324499 6.675284 N 7.822307 3.351753 6.681826 C 16.534488 7.678525 5.052245 C 7.870261 4.627098 6.303211 C 7.834762 4.653894 6.308196 C 15.286926 8.16539 4.710162 C 9.051239 5.248605 5.961215 C 9.014933 5.273135 5.957958 C 14.832985 8.046946 3.386307 C 10.255255 4.522919 5.998879 C 10.217258 4.545114 5.989384 C 15.658307 7.398946 2.458221 C 10.210101 3.180089 6.381903 C 10.171186 3.203431 6.378132 C 13.547353 8.63588 2.959671 C 11.539386 5.180928 5.680797 C 11.505295 5.188917 5.660518 C 13.093024 9.833313 3.519314 C 11.757711 6.508049 6.066304 C 11.737363 6.526372 6.006439 C 12.770646 8.030414 1.956335 C 12.581222 4.498109 5.028283 C 12.544918 4.47149 5.046365 C 11.905056 10.390164 3.079534 C 12.978889 7.103631 5.817187 C 12.977782 7.086875 5.775987 H 13.64863 10.356074 4.289026 H 11.013305 7.09506 6.589528 H 10.993286 7.143176 6.494655 C 11.595616 8.626331 1.552275 C 13.778133 5.146946 4.790366 C 13.765846 5.083249 4.833077 H 13.051721 7.082779 1.513188 H 12.475052 3.47642 4.68531 H 12.424447 3.446156 4.721089 N 11.181925 9.788063 2.113143 N 13.953492 6.432476 5.176344 N 13.96225 6.368974 5.19928

H 11.501273 11.307455 3.483179 H 13.183045 8.117136 6.121594 H 13.199573 8.106047 6.05215 H 10.9416 8.192266 0.809601 H 14.615903 4.679307 4.289789 H 14.603584 4.580079 4.371515 C 9.934471 10.419403 1.624811 C 15.24677 7.093771 4.901512 C 15.263738 7.020157 4.948401 H 10.173472 10.996018 0.730665 H 15.441373 6.997505 3.834522 H 16.021577 6.246162 4.864465 H 9.225722 9.630064 1.391992 H 15.148391 8.144872 5.162258 H 15.161051 7.597603 4.030367 H 9.563919 11.088531 2.397505 H 16.003807 6.581443 5.496577 H 15.481431 7.662005 5.800656 H 10.602849 13.54444 2.816849 H 7.914745 0.106572 8.811729 H 7.91172 0.121415 8.803396 H 9.732356 10.76697 -1.764948 H 4.761979 4.510305 9.406794 H 4.763405 4.505157 9.414413 H 8.610844 11.13397 6.576212 H 7.827336 -1.362435 4.151686 H 7.808997 -1.324897 4.130344 H 8.433241 7.116703 0.375345 H 4.436494 5.163315 5.07066 H 4.400772 5.178978 5.057239 H 17.95593 9.564002 7.255715 H 16.143811 3.031099 5.211111 H 16.192195 2.987579 5.22176 H 15.997778 3.881534 5.147502 H 13.100432 7.32014 1.917848 H 13.071142 7.410395 1.865825 H 19.131056 9.276005 3.243931 H 15.279949 6.162328 7.917252 H 15.283428 6.114609 7.859994 H 17.744956 4.334168 0.46165 H 12.417039 10.652357 5.626661 H 12.394731 10.670776 5.625524 H 15.38742 7.277937 1.416845 H 11.103147 2.568812 6.439207 H 11.062591 2.589723 6.433735 H 17.569734 6.454293 2.15852 H 8.901155 1.568178 7.014679 H 8.863978 1.593927 7.017722 H 14.686609 8.621636 5.486694 H 9.020051 6.281018 5.634546 H 8.982742 6.304893 5.629514 H 16.93933 7.747474 6.051968 H 6.910707 5.123015 6.264734 H 6.876428 5.151897 6.272174

[CPA6 + dMV -4H]^2- Conformer 4 [CPA6 + dMV -4H]^2- Conformer 5 [CPA6 + dMV -4H]^2- Conformer 5

C 0.484377 8.40507 0.440086 C 0.483084 8.41378 0.447911 C 4.586199 6.19703 7.555366 O -0.32686 7.598611 0.946523 O -0.322686 7.60477 0.95898 O 4.534576 6.188053 8.819689 O 1.709952 8.530611 0.74443 O 1.70959 8.544365 0.746355 O 4.735237 5.183825 6.823495 O -0.317288 14.237216 7.753717 O -0.305442 14.250854 7.758347 O 13.440346 8.961194 10.040955 O -1.036544 14.710982 9.833786 O -1.015637 14.724003 9.841662 O 15.158701 7.699063 9.368303 C 5.69918 15.317023 -0.058185 C 5.668688 15.345159 -0.0837 C 9.531842 4.983278 0.638625 H 5.67932 16.410161 -0.042545 H 5.644673 16.438229 -0.069229 H 10.298129 5.420133 -0.005438 O 4.286536 10.80164 0.862098 O 4.278179 10.82554 0.848824 O 6.603138 4.097458 4.303181 O 3.308677 9.738144 -0.886732 O 3.295723 9.75609 -0.893794 O 4.582473 5.117186 4.266071 C 4.124842 10.624029 -0.33099 C 4.111187 10.645847 -0.343225 C 5.664856 4.594143 3.71206 O 0.813353 15.878692 0.687605 O 0.784504 15.88884 0.685765 O 9.99479 9.254312 3.19174 O 5.086257 12.78092 -1.022895 O 5.060747 12.805599 -1.042569 O 6.936395 4.884537 1.639847 C 4.877946 11.430538 -1.394866 C 4.855795 11.453965 -1.411854 C 5.639321 4.700207 2.185426 H 4.351184 11.35224 -2.354276 H 4.324531 11.372443 -2.368507 H 4.956574 5.501471 1.876531 H 5.876472 10.994683 -1.481108 H 5.855555 11.021868 -1.502589 H 5.293619 3.740518 1.794172 C 0.171334 13.528606 -0.730418 C 0.144513 13.53482 -0.726562 C 7.385998 9.097304 4.212649 H -0.428034 14.417079 -0.950662 H -0.459342 14.420749 -0.944788 H 7.799597 10.07654 3.953129 H 0.151427 12.882538 -1.612057 H 0.122702 12.887704 -1.607388 H 6.30346 9.140062 4.072453 C 1.601614 13.957994 -0.474865 C 1.574382 13.969948 -0.478575 C 7.962479 8.054851 3.279834 C 1.884249 15.162966 0.184162 C 1.85565 15.176697 0.17779 C 9.276274 8.145569 2.791861 C 3.209743 15.599083 0.297351 C 3.180003 15.618012 0.283942 C 9.771777 7.153566 1.939911 H 3.444177 16.559419 0.740474 H 3.412961 16.579725 0.724851 H 10.779969 7.23497 1.552648 C 4.271915 14.811948 -0.149813 C 4.242953 14.834465 -0.167655 C 8.987898 6.052905 1.567848

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C 1.527393 11.17559 8.896845 C 1.557061 11.197465 8.896041 C 11.991124 3.174815 11.135332 C 3.441825 12.656045 9.179347 C 3.467159 12.685535 9.167693 C 13.614531 2.177024 9.604257 C 2.669786 7.72382 8.531104 C 2.710884 7.749715 8.528357 C 9.051656 1.029844 11.533719 H 2.001529 6.857938 8.502526 H 2.045837 6.88124 8.503918 H 8.158729 1.361674 12.069612 H 3.358293 7.610392 9.377525 H 3.403882 7.639877 9.371582 H 9.535616 0.215219 12.086828 C 3.311807 14.766402 10.331953 C 3.334564 14.796626 10.318673 C 15.854823 3.027404 9.363412 H 4.102914 15.226078 10.935771 H 4.126735 15.260121 10.91816 H 16.747506 2.678369 8.834062 H 2.650552 14.181328 10.976988 H 2.678694 14.209761 10.96757 H 16.015024 2.922075 10.44276 C 5.811638 11.729781 9.323152 C 5.841183 11.768499 9.300672 C 13.17171 -0.101733 8.539573 H 5.977723 12.473118 10.108848 H 6.008273 12.513267 10.084796 H 14.260399 -0.201525 8.568739 H 6.224556 10.776459 9.666287 H 6.25945 10.817119 9.642713 H 12.739066 -1.009621 8.970921 C 3.459365 7.765642 7.216112 C 3.493978 7.79318 7.20955 C 8.590126 0.442643 10.198817 O 7.966807 15.273847 6.609145 O 7.969334 15.318055 6.572536 O 14.055434 1.143745 3.801308 C 7.094227 8.448564 5.374278 C 7.117237 8.488001 5.349079 C 8.410694 -0.899915 6.493366 C 6.973756 11.25167 7.106031 C 6.994342 11.292586 7.078404 C 11.492253 -0.495325 6.658566 C 7.505877 8.911263 6.793013 C 7.534087 8.953939 6.765235 C 9.498307 -1.728369 7.208868 H 7.397366 8.067709 7.481259 H 7.432315 8.110734 7.454938 H 9.060497 -2.096261 8.140392 H 8.54366 9.258808 6.787578 H 8.57046 9.305538 6.754255 H 9.800969 -2.563408 6.566288 C 7.595031 13.95743 6.79783 C 7.603542 14.000414 6.764357 C 13.268243 0.596048 4.789629 C 6.558174 12.168428 8.082529 C 6.57992 12.208754 8.055951 C 12.737641 -0.004716 7.088702 C 2.508894 15.903171 9.656993 C 2.524004 15.929465 9.646242 C 15.671237 4.526428 9.033266 C 7.697053 11.693963 5.994565 C 7.710476 11.736514 5.962956 C 11.186198 -0.505059 5.294677 H 8.028134 10.972079 5.258714 H 8.040776 11.015147 5.226248 H 10.24595 -0.901532 4.93686 C 6.872244 13.517593 7.907282 C 6.887845 13.558949 7.877757 C 13.60648 0.550621 6.14341 H 6.523038 14.206658 8.665133 H 6.539601 14.247456 8.636559 H 14.542858 0.960335 6.50411 C 8.012838 13.044254 5.816674 C 8.020119 13.087838 5.782121 C 12.064958 0.027888 4.353094 O 1.266262 15.935382 9.796144 O 1.281935 15.95702 9.79136 O 16.029034 5.337911 9.934058 C 7.572692 16.207783 7.593886 C 7.576518 16.251436 7.558322 C 15.187346 1.899097 4.18494 H 8.018137 17.160861 7.291717 H 8.016913 17.205892 7.253115 H 15.581573 2.330042 3.261083 H 7.95941 15.943246 8.585824 H 7.969034 15.989266 8.548609 H 15.951941 1.271015 4.659412 O 3.174207 16.776079 9.013316 O 3.182811 16.804261 8.998469 O 15.200615 4.847708 7.909645 C 3.928507 8.596268 3.01926 C 3.93934 8.621151 3.010013 C 14.671821 7.070604 5.861843 H 4.158278 7.935753 3.850542 H 4.175457 7.962393 3.840913 H 15.281352 6.295754 5.395454 H 4.829002 8.813709 2.442704 H 4.836339 8.841372 2.429079 H 15.083508 7.33595 6.83286 H 3.167071 8.182762 2.36129 H 3.176423 8.204069 2.356032 H 14.574958 7.937474 5.207338 C 2.457848 10.546818 2.914279 C 2.460619 10.565902 2.910043 C 12.82787 6.314648 7.295793 N 3.421774 9.87229 3.572411 N 3.430349 9.895832 3.564201 N 13.315569 6.518886 6.054728 C 3.969521 10.367322 4.70789 C 3.981716 10.394235 4.696446 C 12.598292 6.186912 4.96288 C 3.549276 11.574848 5.221519 C 3.559356 11.60072 5.21079 C 11.359658 5.597074 5.083282 C 2.549412 12.303108 4.553502 C 2.553401 12.324344 4.546894 C 10.852673 5.330437 6.358448 C 2.010318 11.767597 3.380924 C 2.01061 11.785424 3.377587 C 11.588776 5.737049 7.479978 C 2.068346 13.595201 5.075788 C 2.069915 13.615177 5.070048 C 9.59921 4.576291 6.51875 C 2.908076 14.44008 5.816444 C 2.910129 14.46434 5.805238 C 9.379703 3.419161 5.768133 C 0.753634 14.011454 4.836144 C 0.752337 14.025879 4.836709 C 8.628043 4.985324 7.437778 C 2.419706 15.637633 6.293597 C 2.41948 15.660549 6.28342 C 8.208826 2.707801 5.948454 H 3.947645 14.209643 6.012942 H 3.951619 14.238269 5.99656 H 10.108834 3.055994 5.054158 C 0.313688 15.215234 5.345953 C 0.310266 15.228575 5.347243 C 7.489457 4.2262 7.589689 H 0.038774 13.394577 4.311692 H 0.03722 13.405393 4.316884 H 8.734676 5.895634 8.011291

N 1.139502 15.998066 6.065861 N 1.136696 16.015615 6.061838 N 7.300362 3.105911 6.860486 H 3.031886 16.32014 6.861873 H 3.03185 16.346186 6.847709 H 7.980435 1.823233 5.381666 H -0.697363 15.56491 5.210547 H -0.702858 15.574064 5.216669 H 6.708456 4.489789 8.279654 C 0.6356 17.236979 6.686647 C 0.631083 17.253361 6.683565 C 6.050437 2.340196 7.060594 H 1.349945 18.033097 6.480446 H 0.56446 17.07927 7.760382 H 5.919105 1.66439 6.220804 H -0.322961 17.483048 6.23544 H 1.341381 18.051935 6.472933 H 6.150042 1.77735 7.988473 H 0.563087 17.061835 7.762915 H -0.330578 17.495213 6.236696 H 5.238145 3.060735 7.129486 H 2.723285 9.269595 -0.193146 H 2.715629 9.286094 -0.196762 H 4.675853 5.13634 5.287003 H 7.360717 8.746215 2.801623 H 7.369789 8.783811 2.774914 H 6.970122 -0.37091 4.810811 H -1.051318 7.295823 2.38431 H -1.037952 7.299738 2.400862 H 4.904006 4.848823 9.475621 H 5.226495 7.467844 6.458717 H 5.258548 7.501459 6.443955 H 8.408351 0.787262 8.327135 H -2.065519 16.591102 3.735032 H -2.082119 16.593409 3.746165 H 12.292681 10.272104 5.013643 H -0.109229 15.097625 9.899162 H -0.089528 15.114408 9.901725 H 15.569065 6.775225 9.557207 H 1.871137 17.995736 3.973356 H 1.850613 18.014023 3.963963 H 14.148993 6.957586 2.341662 H 4.565621 16.716116 8.919574 H 4.573995 16.749556 8.898073 H 15.476014 3.931459 6.72549 H 1.247926 12.281754 2.808407 H 1.243419 12.296015 2.808298 H 11.230121 5.557406 8.487339 H 2.063598 10.078659 2.024567 H 2.063885 10.095292 2.022729 H 13.483979 6.591608 8.101145 H 3.976525 11.91553 6.157185 H 3.989851 11.944093 6.143983 H 10.806054 5.328954 4.19099 H 4.71235 9.74909 5.189428 H 4.729248 9.779384 5.17503 H 13.065223 6.387494 4.015853

[CPA6 + PTM -4H]^2- Conformer 1 [CPA6 + PTM -4H]^2- Conformer 2 [CPA6 + PTM -4H]^2- Conformer 3

C 13.401634 -1.231865 2.550608 C 13.901904 -1.547921 2.337446 C 13.537798 -1.61906 2.511801 H 12.802909 -0.365564 2.25312 H 13.421583 -0.681744 1.870851 H 12.951191 -0.772925 2.138446 H 14.270748 -1.274385 1.887029 H 14.858075 -1.709433 1.834087 H 14.433293 -1.698014 1.889432 C 12.578365 -2.479587 2.315374 C 13.022952 -2.757926 2.091742 C 12.715277 -2.873968 2.31196 C 13.213655 -3.631436 1.860125 C 13.580817 -3.98201 1.708807 C 13.302273 -4.016534 1.761466 H 14.291883 -3.601143 1.798143 H 14.660988 -4.049775 1.672892 H 14.374138 -4.004613 1.611521 C 12.495857 -4.769372 1.488826 C 12.774239 -5.063567 1.342625 C 12.527401 -5.113477 1.379952 C 11.09078 -4.771383 1.551147 C 11.372607 -4.967648 1.419887 C 11.134937 -5.098867 1.570211 C 10.458412 -3.627344 2.052909 C 10.82471 -3.749962 1.822755 C 10.562069 -3.98076 2.17945 H 9.380673 -3.61789 2.146495 H 9.750334 -3.645255 1.858626 H 9.496036 -3.954715 2.357456 C 11.18593 -2.499668 2.449841 C 11.628804 -2.654089 2.139394 C 11.334874 -2.878522 2.5477 O 13.124618 -5.904038 1.022603 O 13.274942 -6.253097 0.860812 O 13.047613 -6.243241 0.783361 C 14.518807 -5.928714 1.274949 C 14.683441 -6.408442 0.804846 C 14.456729 -6.32558 0.6364 H 14.706816 -5.696243 2.325286 H 14.853704 -7.470456 0.60467 H 14.658252 -7.358683 0.337933 H 15.048963 -5.177831 0.675528 H 15.149197 -6.180302 1.762826 H 14.968996 -6.151438 1.583051 C 15.149575 -7.277092 0.969998 C 15.32531 -5.616578 -0.347938 C 14.988 -5.41352 -0.48563 O 14.545328 -8.245154 0.554415 O 14.792137 -5.496679 -1.428902 O 14.396439 -5.269759 -1.533078 O 16.464988 -7.273458 1.185848 O 16.54448 -5.132991 -0.091173 O 16.172375 -4.840569 -0.250135 O 10.608468 -1.364505 3.00257 O 11.100308 -1.414175 2.474298 O 10.793493 -1.737042 3.118592 C 9.302691 -0.978878 2.569437 C 9.917504 -1.007081 1.787875 C 9.502993 -1.311381 2.676191 H 9.143405 -1.250969 1.521489 H 9.881717 -1.429691 0.779119 H 9.31254 -1.652038 1.653667 H 9.269506 0.109496 2.684254 H 9.964053 0.085527 1.736707 H 9.526068 -0.218189 2.706757 C 8.175471 -1.596724 3.426971 C 8.645743 -1.407629 2.555857 C 8.354743 -1.812098 3.58471

O 7.414185 -2.406897 2.854927 O 7.905378 -2.288378 2.061963 O 7.690411 -2.784859 3.167095 O 8.116027 -1.245088 4.651058 O 8.439104 -0.807056 3.662497 O 8.157379 -1.183162 4.67745 C 10.296096 -5.989099 1.093481 C 10.468814 -6.137269 1.052917 C 10.277028 -6.275831 1.133571 H 10.842991 -6.463217 0.271997 H 10.912185 -6.657691 0.197263 H 10.743293 -6.738523 0.258129 H 9.332649 -5.671208 0.691336 H 9.499662 -5.758976 0.723292 H 9.294521 -5.922156 0.81841 C 10.076711 -7.030055 2.181495 C 10.268933 -7.154797 2.169579 C 10.120359 -7.332931 2.213263 C 11.182335 -7.74538 2.65753 C 11.365226 -7.944277 2.541836 C 11.260718 -8.028746 2.637032 H 12.140581 -7.537634 2.204357 H 12.301072 -7.752592 2.039919 H 12.199731 -7.766003 2.172327 C 11.060107 -8.707365 3.653993 C 11.26602 -8.936618 3.506841 C 11.196709 -9.012743 3.615284 C 9.810611 -8.97294 4.245869 C 10.044118 -9.179267 4.156385 C 9.970419 -9.324817 4.232707 C 8.706024 -8.298566 3.723649 C 8.952145 -8.393983 3.788123 C 8.833818 -8.650833 3.788201 H 7.71678 -8.539305 4.092974 H 7.988981 -8.561609 4.258081 H 7.867236 -8.890813 4.218909 C 8.816081 -7.341436 2.706651 C 9.045954 -7.389918 2.815302 C 8.89219 -7.660532 2.79865 O 12.112261 -9.489837 4.07771 O 12.315119 -9.768088 3.848348 O 12.287048 -9.761673 4.009415 C 13.420609 -9.209911 3.612892 C 13.605406 -9.485033 3.349023 C 13.544613 -9.507638 3.416202 H 13.488536 -9.174347 2.518507 H 13.626172 -9.419465 2.253114 H 13.493419 -9.499892 2.31985 H 14.045446 -10.040415 3.952353 H 14.232148 -10.334158 3.636474 H 14.188573 -10.342216 3.7092 C 13.99525 -7.913441 4.182157 C 14.224897 -8.211943 3.938617 C 14.205015 -8.210628 3.89953 O 15.253185 -7.763113 3.870196 O 15.414884 -7.980759 3.477237 O 15.343433 -7.986299 3.316869 O 13.304505 -7.139079 4.83976 O 13.597277 -7.545606 4.761487 O 13.661279 -7.521356 4.760665 O 7.636004 -6.831556 2.166033 O 7.860124 -6.754584 2.461317 O 7.689139 -7.103662 2.379984 C 7.305146 -5.483142 2.460522 C 7.732635 -5.365035 2.706056 C 7.436912 -5.745432 2.709169 H 7.703536 -4.790471 1.70811 H 7.917382 -4.786419 1.793437 H 7.669639 -5.078017 1.869802 H 7.697918 -5.17848 3.433876 H 8.444235 -5.013544 3.462486 H 8.041601 -5.402396 3.554886 C 5.789731 -5.295966 2.488584 C 6.320791 -5.026196 3.194605 C 5.957161 -5.544252 3.042346 O 4.977817 -6.168965 2.264136 O 5.504039 -5.834808 3.570885 O 5.116979 -6.417501 2.962034 O 5.401189 -4.055067 2.814574 O 6.046014 -3.707597 3.183164 O 5.639676 -4.304694 3.420653 C 13.824328 -3.25707 12.080213 C 13.168546 -3.317848 12.034969 C 13.483102 -3.179637 12.111551 H 13.08308 -2.746811 12.69894 H 12.315916 -2.837518 12.518881 H 12.694196 -2.638917 12.638335 H 14.676867 -3.517049 12.714332 H 13.956457 -3.449648 12.782621 H 14.275977 -3.411601 12.828242 C 14.300128 -2.307033 10.999227 C 13.693641 -2.40944 10.940909 C 14.051442 -2.291986 11.025075 C 15.574984 -2.423819 10.446405 C 15.03145 -2.466225 10.557435 C 15.365314 -2.440016 10.578987 H 16.206749 -3.223918 10.810195 H 15.662515 -3.195141 11.049004 H 15.964431 -3.214972 11.038988 C 16.006781 -1.575459 9.419092 C 15.532694 -1.647204 9.540571 C 15.875301 -1.655865 9.535853 C 15.160831 -0.563147 8.944121 C 14.693735 -0.721347 8.905785 C 15.06371 -0.683226 8.934052 C 13.897274 -0.422282 9.527387 C 13.345078 -0.661055 9.287848 C 13.758974 -0.512848 9.40646 H 13.25141 0.360512 9.153834 H 12.695703 0.036727 8.771578 H 13.146836 0.238251 8.927663 C 13.454535 -1.294428 10.519667 C 12.83978 -1.50527 10.280265 C 13.240185 -1.319243 10.417964 O 17.254249 -1.673638 8.83923 O 16.84561 -1.698385 9.11678 O 17.162732 -1.785407 9.054732 C 17.912536 -2.928142 8.957152 C 17.565106 -2.890204 9.39681 C 17.841738 -2.9999 9.341969 H 18.172416 -3.163194 9.994498 H 17.694334 -3.054036 10.471442 H 17.97867 -3.154803 10.417182 H 18.846451 -2.820843 8.395925 H 18.559433 -2.736874 8.964736 H 18.834164 -2.88877 8.893089 C 17.107779 -4.078289 8.316416 C 16.958262 -4.139482 8.722498 C 17.175399 -4.230027 8.688235 O 16.349572 -3.784221 7.372793 O 16.28278 -3.976205 7.687151 O 16.551886 -4.050138 7.623285 O 17.327654 -5.246563 8.78499 O 17.253882 -5.260693 9.25735 O 17.363478 -5.351503 9.270026 O 12.205529 -1.217753 11.082266 O 11.537168 -1.506556 10.699193 O 11.952962 -1.226157 10.876013 C 11.18293 -0.587062 10.336442 C 10.517433 -0.963464 9.88124 C 11.027013 -0.475333 10.111818 H 11.336487 -0.692377 9.256243 H 10.693967 -1.163214 8.813519 H 11.231667 -0.539928 9.037096

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C 9.137958 -5.100476 10.198242 C 8.854931 -5.647442 9.887862 C 8.997955 -5.275677 9.766252 H 8.867281 -5.561508 9.245252 H 8.634401 -6.155972 8.944431 H 8.856286 -5.911312 8.886992 H 9.725381 -4.201025 10.004351 H 9.390266 -4.720664 9.677982 H 9.588226 -4.399182 9.486607 C 7.848941 -4.735781 10.950958 C 7.523511 -5.351762 10.605044 C 7.612992 -4.835205 10.279562 O 6.826885 -5.428119 10.831276 O 6.616169 -6.199831 10.624576 O 6.626133 -5.578726 10.217665 O 7.834087 -3.68411 11.719126 O 7.347366 -4.20445 11.183971 O 7.479154 -3.641879 10.79431 C 9.65672 -10.007644 5.355056 C 9.931312 -10.260065 5.215245 C 9.895968 -10.340145 5.358225 H 8.612047 -10.322946 5.394456 H 8.905005 -10.630902 5.235254 H 8.887845 -10.758276 5.394012 H 10.254459 -10.886568 5.086738 H 10.581815 -11.094028 4.932867 H 10.591815 -11.157954 5.144813 C 10.085683 -9.569426 6.755111 C 10.311416 -9.811686 6.6195 C 10.235144 -9.768065 6.728841 C 11.44558 -9.409641 7.055356 C 11.65504 -9.589796 6.966312 C 11.57253 -9.5285 7.086992 H 12.156207 -9.568745 6.258248 H 12.405663 -9.695565 6.194124 H 12.338637 -9.712103 6.345172 C 11.883258 -9.044491 8.327695 C 12.017424 -9.24336 8.268876 C 11.912584 -9.067362 8.358932 C 10.958823 -8.818886 9.359694 C 11.036119 -9.096117 9.264271 C 10.912408 -8.826435 9.31725 C 9.606323 -8.995672 9.073018 C 9.70634 -9.299063 8.915409 C 9.588444 -9.03977 8.952513 H 8.89339 -8.774912 9.8535 H 8.957922 -9.128054 9.674085 H 8.82588 -8.805824 9.680008 C 9.163229 -9.355288 7.794037 C 9.335469 -9.644965 7.612014 C 9.238218 -9.492905 7.676333 O 13.207059 -8.914039 8.666491 O 13.309007 -9.071864 8.694773 O 13.195834 -8.87063 8.793546 C 14.11955 -8.578392 7.627539 C 14.306412 -8.716767 7.747845 C 14.240571 -8.713305 7.841228 H 13.672716 -7.870724 6.930128 H 13.923536 -8.031498 6.990878 H 13.941761 -8.076309 7.00692 H 14.424931 -9.472321 7.061287 H 14.698498 -9.606617 7.230652 H 14.555857 -9.688205 7.438177 C 15.356642 -7.96279 8.276445 C 15.439401 -8.052472 8.530271 C 15.408463 -8.084055 8.603273 O 15.823226 -8.375459 9.325701 O 15.795775 -8.439571 9.630678 O 15.761433 -8.488242 9.699394 O 15.834184 -6.971703 7.549646 O 15.961058 -7.04194 7.860092 O 15.953184 -7.087411 7.933748 O 7.817708 -9.467799 7.464944 O 8.010964 -9.815363 7.230714 O 7.918263 -9.676163 7.285499 C 6.840899 -9.680849 8.466114 C 7.09659 -10.321909 8.18438 C 6.960745 -10.030732 8.267148 H 7.227558 -10.332516 9.26447 H 7.560301 -11.097273 8.809978 H 7.386238 -10.726368 9.004284 H 6.006418 -10.193578 7.983092 H 6.282258 -10.78824 7.621664 H 6.153471 -10.550423 7.743782 C 6.2557 -8.433768 9.144416 C 6.463063 -9.299948 9.13374 C 6.316644 -8.883793 9.058422 O 5.11139 -8.422074 9.559714 O 5.582172 -9.635151 9.904854 O 5.358584 -9.089278 9.778918 O 7.133971 -7.450764 9.26199 O 6.984295 -8.095714 9.007501 O 6.936809 -7.731638 8.878734 N 7.69056 -1.878327 7.375325 N 6.484701 -1.797159 5.263982 N 7.338713 -1.23566 7.331452 N 6.773919 -2.177432 9.448306 N 7.497715 -1.024613 7.176498 N 6.386406 -1.325654 9.408037 C 6.746489 -2.405287 8.14315 C 6.528974 -1.710314 6.589245 C 6.393939 -1.702942 8.137185 C 5.663911 -3.233526 7.575457 C 5.477282 -2.410638 7.350617 C 5.333524 -2.601875 7.635126 C 5.031935 -4.194164 8.387232 C 4.267446 -2.724603 6.704694 C 4.69611 -3.483521 8.526233 H 5.379733 -4.391369 9.395801 H 4.039864 -2.293101 5.735675 H 5.048544 -3.599326 9.546358 C 4.016773 -4.990352 7.881065 C 3.367438 -3.608107 7.278929 C 3.686835 -4.324995 8.08007 H 3.581247 -5.780845 8.482345 H 2.454588 -3.872573 6.757117 H 3.224492 -5.042 8.748875 C 3.608597 -4.845105 6.549075 C 3.680562 -4.212105 8.50509 C 3.313424 -4.320651 6.732214 C 4.204276 -3.862414 5.742435 C 4.802578 -3.789076 9.226364 C 3.934537 -3.438371 5.838565 H 3.915612 -3.753164 4.70466 H 5.01955 -4.246019 10.18444 H 3.676319 -3.469014 4.78767 C 5.240723 -3.08291 6.245418 C 5.70211 -2.900192 8.648658 C 4.944551 -2.594123 6.285404 H 5.723215 -2.362586 5.590598 H 6.601854 -2.63359 9.192685 H 5.43836 -1.938347 5.574754 C 2.857618 -6.3969 4.852595 C 2.609357 -6.346461 8.197479 C 2.794493 -6.297842 5.471513 H 3.457208 -5.803853 4.158738 H 2.305463 -6.02074 7.194274 H 3.412387 -5.925774 4.646728 H 1.863307 -6.513944 4.410916 H 1.733175 -6.785688 8.682589 H 1.861292 -6.675334 5.045949 C 3.495152 -7.772191 5.082186 C 3.736559 -7.391819 8.120035 C 3.523575 -7.409155 6.262263

H 3.671888 -8.198843 4.086177 H 3.248317 -8.374411 8.084134 H 3.043263 -8.368926 6.034258 H 2.772472 -8.418897 5.595144 H 4.283231 -7.370287 9.068322 H 3.354019 -7.234344 7.331676 C 4.808311 -7.755068 5.885762 C 4.717911 -7.319638 6.932455 C 5.030094 -7.541705 5.980912 H 5.195226 -8.780495 5.950718 H 4.162834 -7.322037 5.985127 H 5.175417 -7.779899 4.921761 H 4.592854 -7.452244 6.915531 H 5.294429 -8.25214 6.939878 H 5.420113 -8.390957 6.553223 C 5.873566 -6.84165 5.276353 C 5.698727 -6.1371 6.936552 C 5.831822 -6.284319 6.320141 H 6.178882 -7.230888 4.303686 H 5.245426 -5.268953 6.457038 H 5.488632 -5.450087 5.708452 H 5.45345 -5.85657 5.084315 H 5.944807 -5.855932 7.962429 H 5.682431 -6.001469 7.365011 C 7.085683 -6.614396 6.161618 C 6.995319 -6.451719 6.20827 C 7.314268 -6.449841 6.069086 H 6.793902 -6.38441 7.189848 H 7.596398 -7.137644 6.806275 H 7.767256 -7.08728 6.828878 H 7.739531 -7.485854 6.179809 H 6.807418 -6.889954 5.226251 H 7.501721 -6.898651 5.091855 C 9.051961 -5.205862 5.971155 C 9.025459 -5.089364 6.104216 C 9.246243 -5.02541 6.19361 C 9.84513 -6.005735 6.801304 C 9.897987 -6.172293 6.283811 C 10.116977 -6.123571 6.179228 H 9.461528 -6.908028 7.252422 H 9.538408 -7.189748 6.309364 H 9.755348 -7.131654 6.041557 C 11.16568 -5.630853 7.036718 C 11.260306 -5.941252 6.429301 C 11.478519 -5.919355 6.358475 H 11.788915 -6.252416 7.670032 H 11.913811 -6.790748 6.579581 H 12.129487 -6.781647 6.363133 C 11.680122 -4.447734 6.496108 C 11.777954 -4.639442 6.406562 C 11.992479 -4.629887 6.542123 C 10.867561 -3.631802 5.698239 C 10.907381 -3.560314 6.169944 C 11.119088 -3.529419 6.500422 H 11.253048 -2.712494 5.27489 H 11.287475 -2.54624 6.091405 H 11.497246 -2.516657 6.580917 C 9.569669 -4.025223 5.425084 C 9.549615 -3.786393 6.004052 C 9.760344 -3.724369 6.320944 H 8.926037 -3.438355 4.790438 H 8.877008 -2.965816 5.794528 H 9.0907 -2.879168 6.269261 C 13.085329 -4.085445 6.761771 C 13.203872 -4.414063 6.697277 C 13.42258 -4.43368 6.815535 N 13.356014 -2.901697 7.305818 N 13.556317 -3.352908 7.415575 N 13.798717 -3.452863 7.631963 H 14.315449 -2.61609 7.462668 H 14.540638 -3.203403 7.632146 H 14.790096 -3.295669 7.79593 H 12.61272 -2.247881 7.506092 H 12.86917 -2.798614 7.900253 H 13.127307 -2.947347 8.186911 N 14.028021 -4.94999 6.481882 N 14.123127 -5.256299 6.27559 N 14.329064 -5.215511 6.267048 O 2.640817 -5.696188 6.103091 O 2.915743 -5.209005 9.035746 O 2.351335 -5.199628 6.318944 O 7.76752 -5.473753 5.616031 O 7.675634 -5.18663 6.007669 O 7.894982 -5.129068 6.101178 H 8.665309 -3.031649 11.607307 H 8.148207 -3.48369 11.082823 H 8.325112 -3.010493 10.747083 H 6.841982 -6.695533 9.86838 H 6.724457 -7.425246 9.735602 H 6.65638 -6.972561 9.485384 H 16.516124 -6.401882 8.049183 H 16.566494 -6.463067 8.435803 H 16.594247 -6.531398 8.494962 H 17.749352 -5.358465 10.354787 H 17.536828 -5.251357 10.852353 H 17.620464 -5.340653 10.86779 H 9.109516 -0.229264 5.180222 H 9.357398 0.230909 4.146493 H 9.120134 -0.063213 4.992854 H 6.168666 -3.430575 2.965693 H 6.778066 -3.146247 2.767801 H 6.435616 -3.689552 3.46832 H 16.748853 -6.442442 1.681862 H 16.752502 -5.162047 0.881116 H 16.450348 -4.935803 0.700381 H 6.088406 -2.601165 10.050882 H 7.602875 -0.960931 8.202029 H 5.771967 -1.807358 10.043657 H 7.555976 -1.603628 9.856943 H 8.323115 -0.744336 6.645374 H 7.260777 -0.864161 9.784412 H 7.729225 -2.005289 6.363865 H 5.973033 -2.557719 4.829303 H 7.424673 -1.485052 6.341602 H 8.451554 -1.350157 7.79606 H 7.215969 -1.368001 4.670016 H 8.109516 -0.700559 7.725189 H 15.011978 -4.739754 6.690503 H 15.082268 -5.171441 6.609416 H 15.296107 -5.165 6.583624 H 13.817119 -5.750456 5.880453 H 13.92173 -6.005472 5.608833 H 14.096165 -5.92698 5.57302 H 15.618191 -6.784903 4.104323 H 15.865355 -7.030651 3.891873 H 15.834462 -7.054356 3.709657

[CPA6 + PTM -4H]^2- Conformer 4 [CPA6 + PTM -4H]^2- Conformer 5 [CPA6 + PTM -4H]^2- Conformer 6

C 13.529641 -1.628169 2.505949 C 14.758662 -2.106946 1.340492 C 14.669131 -2.05597 1.357903 H 12.941049 -0.783854 2.1316 H 14.328267 -1.290099 0.749671 H 14.227782 -1.222209 0.801936