Homologation of Boronic Esters with Organolithium Compounds: A Computational Assessment of Mechanism

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Homologation of Boronic Esters with Organolithium Compounds: A Computational Assessment of Mechanism Stéphanie Essafi,*,1 Simone Tomasi, 2 Varinder K. Aggarwal, 1 Jeremy Harvey*,1 1 School of Chemistry, University of Bristol, Cantock s Close, Bristol, BS8 1TS, U.K. 2 AstraZeneca, Pharmaceutical Development, Charter Way, Macclesfield, Cheshire SK10 2NA Additional Computational Details... 2 Additional Discussion... 3 Sample Molpro Files... 6 Energies and Frequencies... 8 Cartesian coordinates... 10 1

Additional Computational Details Coupled-cluster calculations were performed using the Molpro 2010.1 package. 1 A density-fitted local correlation treatment 2 was used all along. For the composite method, local coupled-cluster calculations as well as local MP2 calculations were performed. In the latter case, additional calculations using explicit treatment of electron-electron correlation (F12 method) were performed in order to approach the infinite basis set limit and correct for domain effects. The specially optimized correlation consistent VDZ-F12 basis set 3 was used for the LMP2-F12 (ansatz = 3*A(loc)) calculations 4 along with a suitable combination of auxiliary basis sets (see below for a sample input file). The aug-cc-pvdz (AVDZ) basis set was used for LMP2 and LCCSD(T0) calculations along with a similar combination of auxiliary basis sets (see below for a sample input file). The valence orbitals were localized using the Pipek-Mezey procedure. The orbital domains were determined automatically using the procedure of Boughton and Pulay along with the default completeness criterion of 0.980. In order to improve the localization, contribution of the two most diffuse basis function of each angular momentum was removed (keyword pipek,delete=2) in LMP2 and LMP2-F12 calculations. Composite electronic energies at the LCCSD(T0)-F12 level of theory were estimated as: ( ) The first term corresponds to the DF-LMP2-F12 energy. The difference between the two remaining terms introduces higher-order correlation effects through coupled cluster calculations. In these calculations, strong pairs are treated at the CCSD level whereas weak and distant pairs are treated at the MP2 level. 1 (a) MOLPRO, version 2010.1, a package of ab initio programs, H.-J. Werner, P. J. Knowles, G. Knizia, F. R. Manby, M. Schütz, P. Celani, T. Korona, R. Lindh, A. Mitrushenkov, G. Rauhut, K. R. Shamasundar, T. B. Adler, R. D. Amos, A. Bernhardsson, A. Berning, D. L. Cooper, M. J. O. Deegan, A. J. Dobbyn, F. Eckert, E. Goll, C. Hampel, A. Hesselmann, G. Hetzer, T. Hrenar, G. Jansen, C. Köppl, Y. Liu, A. W. Lloyd, R. A. Mata, A. J. May, S. J. McNicholas, W. Meyer, M. E. Mura, A. Nicklass, D. P. O'Neill, P. Palmieri, D. Peng, K. Pflüger, R. Pitzer, M. Reiher, T. Shiozaki, H. Stoll, A. J. Stone, R. Tarroni, T. Thorsteinsson, and M. Wang,, see http://www.molpro.net. (b) Werner, H.-J., Knowles, P. J., Knizia, G., Manby, F. R., Schütz, M. Molpro: a general-purpose quantum chemistry program package. WIREs Comput. Mol. Sci. 2, 242-253 (2012). 2 Adler, T. B., Werner, H.-J. & Manby, F. R. Local explicitly correlated second-order perturbation theory for the accurate treatment of large molecules. J. Chem. Phys. 130, 054106 (2009). 3 For VnZ-F12 basis sets: Peterson, K. A., Adler, T. B. & Werner, H.-J. Systematically convergent basis sets for explicitly correlated wavefunctions: The atoms H, He, B Ne, and Al Ar. J. Chem. Phys. 128, 084102 (2008). For auxiliary basis: Yousaf, K. E. & Peterson, K. A. Optimized auxiliary basis sets for explicitly correlated methods. J. Chem. Phys. 129, 184108 (2008). 4 Werner, H.-J. Eliminating the domain error in local explicitly correlated second-order Møller Plesset perturbation theory. J. Chem. Phys. 129, 101103 (2008). 2

Triple excitations were treated perturbatively using the (T0) approximation. Integral direct algorithms were used as recommended for large molecules. Additional Discussion It is interesting to cross-check the methodology used for computing relative potential energies by considering the relative free energies for all the conformers of 4a as predicted by three different methods, see Figure S1. Though the order in relative free energies of different conformers with different methods is broadly conserved, there is a systematic difference in the magnitude of these values, as already discussed above. B3LYP-D2 systematically overestimates the exoergicity of formation of the ate complex. LCCSD(T0)-F12 values lie between 6 and 13 kcal mol 1 above the B3LYP-D2 ones, while the B3LYP- D3 values are intermediate. There is a considerable spread in the differences between the values obtained with different methods. Figure S1. Free energies (kcal mol 1 ) computed for various conformers of 4a with respect to separated reactants. The level of theory refers to electronic energies only. Entropic and bulk solvent contributions were estimated at the B3LYP-D2/6-31+G(d) level of theory. 3

Scheme S1. Conformational analysis of the ate complex 4b. Gibbs free energies in solution (Et 2 O) computed at the LCCSD(T0)-F12/VDZ-F12//B3LYP-D2/6-31+G(d) level of theory (see text for details) and given with respect to the separated reactants MeBpin + Me 2 CLiOCb.2Me 2 O. A conformational analysis has been performed for 4b, though here only disolvated structures were considered based on the analysis for 4a and inspection of the structures to be favoured (Figure S1). Initial structures were generated from conformers of 4a by simply replacing the H atom with a methyl group. The five most stable conformers of 4a (A, B, G, H and I) as well as the conformer C were used. The latter was optimized for comparison purposes only. As for 4a, C-2solv is found to be strongly disfavoured, lying more than 20 kcal mol 1 above the lowest conformer. This again highlights the importance of the lithium-pinacol interaction. Despite the fact that the ate complex 4b is symmetric (neglecting the counter-cation), it is interesting to note that the conformers A and B do not have the same free energy ( -2.1 kcal mol 1 and -11.1 kcal mol 1 respectively). These two conformers might be expected to be equivalent upon cursory inspection, but in fact when started from input geometries generated from 4a, different structures were obtained. A-2solv displays an additional lithium-ch 3 interaction with the migrating group (Li O pinacol = 2.065 Å; Li H terminus = 2.256 Å; Li H migrating = 1.971 Å; Li O carbamate = 1.878 Å and Li O solvent = 1.996 / 2.176 Å) which is absent in B-2solv. The 4

same is true for the pair of conformers G and H, although in that case the difference in free energy is within the error of the computational method. Both structures G-2solv and H-2solv are similar, the lithium ion sitting between one oxygen of the pinacol, the carbamate, one methyl group on the migrating terminus (η 1 Li-H interaction) and the two solvent molecules. Scheme S2. Conformational analysis of the ate complex 4c. Gibbs free energies in solution (Et 2 O) computed at the LCCSD(T0)-F12/VDZ-F12//B3LYP-D2/6-31+G(d) level of theory (see text for details) and given with respect to the separated reactants MeBpin + MeCPhLiOCb.2Me 2 O. The same approach as described for 4b was used to generate conformers of 4c. Extra care had to be taken here with regard to the orientation of the phenyl group. This resulted in generation of two or three different input structures for some cases, but geometry optimization always converged to a unique conformer. Contrarily to what was expected, conformers A-2solv and G-2solv do not display any significant lithium-π interaction. Lithium interacts weakly with two carbons of the phenyl ring in A-2solv (Li Cphenyl = 2.513 / 2.522 Å) while it sits far from the aromatic in G-2solv (Li Cphenyl > 3.4 Å). On the other hand, lithium seems to interact more strongly with the phenyl ring in C-2solv (Li Cphenyl = 2.366 up to 2.600 Å). Lithium is slightly shifted from the top of the ring towards the migrating terminus to accommodate the much stronger lithium-carbamate interaction. The presence of a lithium-π interaction 5

in C-2solv certainly explains why this conformer is found less disfavoured in 4c (11.4 kcal mol 1 above G-2sol) than in 4a and 4b (respectively 18.1 and 24.3 kcal mol 1 above G-2sol). The conformers appear broadly in the same order as previously. G-2solv is the lowest in free energy, closely followed by H- 2solv. Sample Molpro Files LMP2 and LCCSD(T0) calculations memory,500,m gdirect symmetry,nosym,noorient geometry={ nb of atoms title geometry }! direct integral evaluations! recommended for local calculations basis=vdz hf basis={ default=avdz set,hf default=avdz/jkfit li=def2-atzvpp/jkfit set,df default=avdz/mp2fit set,cc default=avtz/mp2fit } df-hf,df_basis=hf locali,pipek;pipek,delete=2 df-lccsd(t0),basis_mp2=df,basis_ccsd=cc! accurate approximation of 4-external integrals in LCCSD! requires larger fitting basis sets than LMP2 LMP2-F12 calculations memory,500,m gdirect symmetry,nosym,noorient geometry={ nb of atoms! direct integral evaluations! recommended for local calculations 6

title geometry } basis=vdz hf basis={ default=vdz-f12 set,hf default=avdz/jkfit li=def2-atzvpp/jkfit set,df default=avdz/mp2fit set,jk default=vdz/jkfit li=def2-tzvpp/jkfit set,rib default=vdz-f12/optri } df-hf,df_basis=hf locali,pipek;pipek,delete=2 df-lmp2-f12,df_basis=df,df_basis_exch=jk,ri_basis=rib,ansatz=3*a(loc) 7

Energies and Frequencies E (Hartree) H (Hartree) G (Hartree) Low frequencies (cm -1 ) 1-451.246261-451.015836-451.064812 29.4115 104.6822 116.0497 2a -719.461756-719.123241-719.200283 17.1329 36.3250 45.5317 3a -1015.675112-1015.191229-1015.283718 13.3825 25.0928 29.1888 a TS 3a-4a -1015.581041-1015.096518-1015.186001-99.7068 26.7959 33.5604 4a - A-1solv -1015.714017-1015.228612-1015.313265 27.1079 44.3668 55.9377 4a - A-2solv -1170.774402-1170.201058-1170.297160 27.8578 40.8769 53.5188 4a - A-3solv -1325.826329-1325.165552-1325.273343 29.6534 37.2840 39.4957 4a - B-1solv -1015.710427-1015.224789-1015.311783 22.0798 40.4656 42.6255 4a - B-2solv -1170.770167-1170.197140-1170.294207 32.3081 35.3664 47.5107 4a - B-3solv -1325.820559-1325.159525-1325.266457 25.4484 41.1673 49.9514 4a - C-2solv -1170.739556-1170.166257-1170.266313 17.9728 23.8294 36.9848 4a - C-3solv -1325.802052-1325.141860-1325.254438 15.1581 26.9786 34.7336 4a - D-2solv -1170.740078-1170.166576-1170.266640 17.5994 30.3561 33.0333 4a - D-3solv -1325.804474-1325.143170-1325.253847 24.8902 27.0393 34.5704 4a - E-2solv -1170.740186-1170.166171-1170.264641 19.3890 29.9937 41.4035 4a - E-3solv -1325.805405-1325.143627-1325.252136 24.9069 32.4602 41.5728 4a - G-1solv -1015.712484-1015.226976-1015.314642 19.8421 27.6687 31.4855 4a - G-2solv -1170.774674-1170.202291-1170.302555 16.2167 27.4432 36.1056 4a - H-1solv -1015.710703-1015.224735-1015.311022 22.1775 33.1264 44.4474 4a - H-2solv -1170.770324-1170.197332-1170.296886 17.8650 22.8260 30.1849 4a - I-1solv -1015.711542-1015.226126-1015.311998 16.4557 39.1732 42.1405 4a - I-2solv -1170.770837-1170.198035-1170.296466 20.0018 25.2320 32.8315 TS 4a-5a - A-2solv -1170.738964-1170.168768-1170.268912-405.5182 17.2581 25.3454 TS 4a-5a - B-2solv -1170.732195-1170.162011-1170.262048-446.7639 21.5372 34.6685 5a -529.878942-529.588820-529.644323 12.9956 68.3917 105.2029 6-640.919128-640.637751-640.708982 23.5525 29.7568 32.9842 a Geometry optimization performed without dispersion. 8

E (Hartree) H (Hartree) G (Hartree) Low frequencies (cm -1 ) 2b -758.786061-758.418536-758.497380 25.5519 40.9251 48.7660 3b -1055.002514-1054.489366-1054.581798 17.0282 28.5148 49.8067 TS 3b-4b -1055.002453-1054.490098-1054.579477-47.2306 27.8009 31.1374 4b - A-2solv -1210.088415-1209.485707-1209.584568 24.3229 39.5156 56.5189 4b - B-2solv -1210.093937-1209.491708-1209.590331 35.2774 40.0881 47.0334 4b - C-2solv -1210.051016-1209.448449-1209.550169 14.7220 27.9505 37.9385 4b - G-2solv -1210.094678-1209.492925-1209.594475 24.4797 30.7788 43.0268 4b - H-2solv -1210.093888-1209.491736-1209.593516 17.0624 22.2491 30.6311 4b - I-2solv -1210.090377-1209.487922-1209.587461 18.3191 32.2388 38.7636 TS 4b-5b - B-2solv -1210.066384-1209.467148-1209.569313-283.5902 20.1319 33.9803 5b -569.199810-568.880473-568.938350 13.6118 65.5840 105.4361 E (Hartree) H (Hartree) G (Hartree) Low frequencies (cm -1 ) 2c -950.553983-950.129611-950.215829 22.8411 33.4698 42.5515 3c -1246.761765-1246.192184-1246.293350 14.6643 24.2394 38.3382 TS 3c-4c -1246.757774-1246.188631-1246.285384-117.7744 20.5545 27.3473 4c - A-2solv -1401.842406-1401.183829-1401.287592 22.3619 30.0297 57.0462 4c - B-2solv -1401.840411-1401.182143-1401.289465 25.8338 31.5144 38.8516 4c - C-2solv -1401.820155-1401.162954-1401.271452 24.3061 28.4624 34.0845 4c - G-2solv -1401.847938-1401.189336-1401.297209 19.5716 32.4323 42.0708 4c - H-2solv -1401.840278-1401.181886-1401.291362 16.6475 21.6863 30.8597 4c - I-2solv -1401.847938-1401.189336-1401.297209 19.0277 29.6086 34.1521 TS 4c-5c - A-2solv -1401.822442-1401.166631-1401.273692-178.2557 27.8503 31.5762 TS 4c-5c - B-2solv -1401.823073-1401.167007-1401.275802-202.2995 17.5491 33.4247 5c -760.949557-760.573691-760.638628 23.5338 29.4077 51.0847 9

Cartesian coordinates B -1.5774-0.0151-0.0161 O -0.8073-1.0797 0.3963 C 0.5755-0.7809 0.0544 C 0.8622-1.4702-1.2838 C -3.1491-0.0123-0.0037 O -0.8174 1.0592-0.4241 C 0.5628 0.7856-0.0527 C 1.4878 1.3618-1.1183 C 0.8094 1.4794 1.2912 C 1.4880-1.3408 1.1393 H -3.5562 0.6014-0.8181 H -3.5195 0.4244 0.9368 H -3.5639-1.0254-0.0775 H 1.9069-1.3264-1.5841 H 0.6688-2.5434-1.1772 H 0.2125-1.0741-2.0727 H 1.4209-2.4348 1.1447 H 2.5297-1.0576 0.9403 H 1.2042-0.9709 2.1286 H 1.4018 2.4544-1.1250 H 2.5298 1.0965-0.8977 H 1.2308 0.9872-2.1132 H 0.5996 2.5490 1.1804 H 0.1503 1.0719 2.0664 H 1.8497 1.3534 1.6135 O -0.5220-0.8199-0.3985 N -2.7627-0.3707-0.4219 C -3.9252 0.2852 0.1623 C -3.0487-1.5487-1.2258 Li 1.1131-0.0486 0.2045 O 2.1019 0.7656-1.3140 C 1.0366 1.4242-2.0013 C 2.9394 1.6902-0.6182 O 2.2492-1.5514 0.7230 C 2.3006-2.3795-0.4383 C 1.5323-2.1653 1.7930 H -0.0713 0.8831 2.4629 H -3.7775-1.2859-2.0037 H -3.6387 1.2457 0.5907 H 2.0449-3.0850 2.1143 H 1.5060-1.4411 2.6111 H 2.8151-1.8027-1.2108 H 2.8549-3.3049-0.2191 H 3.7112 1.0996-0.1162 H 3.4063 2.3884-1.3301 H 0.4426 0.6443-2.4826 H 0.4098 1.9733-1.2861 H -4.3783-0.3382 0.9505 H -4.6726 0.4438-0.6258 H -2.1301-1.9082-1.6913 H -3.4784-2.3542-0.6074 H 0.5062-2.3979 1.4744 H 1.2824-2.6213-0.7748 H 2.3505 2.2415 0.1279 H 1.4449 2.1160-2.7542 H 0.8482 3.1048 2.0108 H 0.0138 3.2019 0.4520 H -0.9287 3.1730 1.9562 O 0.0000 0.5944 0.0000 C -1.1719-0.1974 0.0000 C 1.1718-0.1974 0.0000 H 2.0258 0.4869 0.0000 H 1.2172-0.8399 0.8966 H 1.2172-0.8399-0.8966 H -2.0258 0.4868 0.0000 H -1.2172-0.8400-0.8966 H -1.2172-0.8400 0.8966 C -1.4854-0.1397 0.0275 O -1.3951 0.8423 0.8948 C 0.0135 1.2288 1.4190 C -0.0355 2.7503 1.4566 C -1.8224 1.3095 1.2696 C -2.6133 2.6085 1.3358 H -1.9526 3.3880 1.7477 H -2.9393 2.9574 0.3418 H -3.5159 2.5705 1.9762 O -2.9113 0.2486 0.9721 C -2.5933-0.7521 0.1829 O -1.4729-0.9243-0.3511 N -3.6277-1.6250-0.0551 C -3.3693-2.8833-0.7378 H -4.2189-3.1183-1.3920 C -4.8844-1.5594 0.6795 H -5.0755-0.5373 1.0066 B 2.1971 0.5602 1.4512 10

C 1.7164 1.5121 2.5981 H 2.1496 2.5160 2.4642 H 2.0254 1.1564 3.5889 H 0.6253 1.6264 2.5718 H -2.4599-2.7980-1.3342 H -3.2494-3.7081-0.0158 H -4.8640-2.2200 1.5618 H -5.6957-1.8900 0.0182 H -1.5698 1.0394 2.3095 O 3.3192-0.2262 1.4763 O 1.5160 0.4392 0.2489 C 2.3604-0.3148-0.6813 C 3.2849-1.1013 0.3089 C 2.6698-2.4275 0.7653 H 2.6611-3.1551-0.0545 H 3.2666-2.8293 1.5915 H 1.6403-2.2809 1.1113 C 4.7084-1.3158-0.1887 H 5.2813-1.8642 0.5676 H 4.6984-1.9064-1.1137 H 5.2097-0.3632-0.3826 C 1.4740-1.1800-1.5669 H 0.8656-0.5351-2.2089 H 2.1019-1.8192-2.2008 H 0.8000-1.8048-0.9772 C 3.1068 0.7206-1.5255 H 2.3697 1.3375-2.0497 H 3.7337 1.3630-0.8958 H 3.7458 0.2271-2.2668 Li -0.3867 0.6162-0.0789 O -0.2943 1.6824-1.8019 C -1.6498 1.5884-2.2432 H -2.3323 1.7790-1.4047 H -1.8338 2.3109-3.0534 H -1.7932 0.5674-2.6042 C 0.0053 2.9755-1.2752 H -0.1342 3.7429-2.0526 H -0.6367 3.1845-0.4092 H 1.0515 2.9504-0.9592 C -0.8072 0.1516 1.7664 Li -0.2508 1.0758-0.1134 C -1.5461 1.2644 2.5175 H -0.8199 1.8381 3.1082 H -2.3182 0.8946 3.2155 H -2.0400 1.9768 1.8391 O -1.9328-0.7503 1.2154 C -2.3298-0.5633-0.0249 O -1.7917 0.2376-0.8268 N -3.4047-1.3261-0.3948 C -3.8750-1.3117-1.7704 H -3.3656-0.5189-2.3168 H -4.9582-1.1339-1.7950 H -3.6741-2.2748-2.2628 C -4.0146-2.3106 0.4879 H -3.6810-2.1479 1.5111 H -3.7464-3.3330 0.1826 H -5.1071-2.2146 0.4433 O -0.3364 2.9716-0.7014 C -1.5717 3.5713-1.0794 H -1.8750 4.3306-0.3444 H -2.3121 2.7708-1.1175 H -1.4821 4.0409-2.0696 C 0.7462 3.8933-0.6448 H 1.6367 3.3223-0.3778 H 0.5579 4.6682 0.1124 H 0.8941 4.3730-1.6232 O 1.6529 0.5834-0.1846 C 2.2742-0.4866-0.9614 B 1.7206 0.2262 1.1931 C 2.1915-1.7198 0.0264 C 1.5115-0.6564-2.2754 C 3.7129-0.0315-1.2488 O 2.1613-1.0810 1.3238 C 1.9633 1.2857 2.3386 C 0.9088-2.5495-0.1245 C 3.4063-2.6506-0.0169 H 1.9236-1.4921-2.8541 H 1.6107 0.2513-2.8818 H 0.4466-0.8389-2.1115 H 3.6840 0.9219-1.7874 H 4.2499-0.7580-1.8689 H 4.2783 0.1195-0.3236 H 1.4625 2.2430 2.1586 H 0.8627-3.2745 0.6950 H 0.8948-3.1000-1.0724 H 0.0166-1.9244-0.0625 H 3.5152-3.1099-1.0073 H 3.2725-3.4540 0.7154 H 4.3320-2.1248 0.2297 H 3.0436 1.4890 2.4162 H 1.6400 0.9133 3.3171 H -0.4070-0.5388 2.5168 Conformers of 4a. C -1.7124 0.5626 2.2181 B -0.9408-0.4388 1.1593 O -1.6752-1.6082 0.6823 C -2.1770-1.3499-0.6217 C -3.5430-0.6447-0.5263 C 0.4842-0.8565 1.9171 11

O 1.6085-1.1322 0.9846 C 2.2605-0.1073 0.4604 N 3.2310-0.4724-0.4235 C 3.4073-1.8480-0.8762 C 0.3371-2.1285 2.7398 O 2.0514 1.0895 0.7579 C 3.8956 0.5458-1.2238 O -0.6836 0.3687-0.1176 C -1.0820-0.4117-1.2443 C -1.5965 0.5160-2.3453 C -2.3511-2.6776-1.3598 C 0.1213-1.2043-1.7754 Li 0.2579 1.5542 0.9340 O -0.2358 3.3591 0.5121 C 0.4528 3.5359-0.7284 C -1.6529 3.4818 0.3607 H -0.4482-1.9746 3.4901 H 0.0201-2.9560 2.0956 H 1.2691-2.3971 3.2563 H 3.4281 0.6270-2.2183 H 3.0451-2.5440-0.1198 H -1.8474 0.0826 3.1991 H -2.7026 0.8782 1.8639 H -1.1439 1.4926 2.4297 H 3.8366 1.5103-0.7177 H 4.9477 0.2655-1.3554 H 4.4761-2.0227-1.0495 H 2.8608-2.0225-1.8145 H 0.8479-0.0515 2.5734 H -0.1355-1.7363-2.7002 H 0.9420-0.5077-1.9885 H 0.4611-1.9266-1.0305 H -0.7700 1.1195-2.7436 H -2.0183-0.0708-3.1717 H -2.3709 1.1902-1.9671 H -3.1484-3.2588-0.8810 H -2.6285-2.5058-2.4089 H -1.4291-3.2662-1.3265 H -4.1985-1.2437 0.1161 H -3.4372 0.3503-0.0836 H -4.0114-0.5423-1.5141 H -2.0276 2.6901-0.3007 H -2.0904 3.3638 1.3541 H -1.8989 4.4731-0.0468 H 0.0957 2.8027-1.4653 H 0.2905 4.5557-1.1063 H 1.5133 3.3681-0.5258 C -0.2362 0.2846 1.8492 C 0.1378 0.4218 3.3185 H 0.0104-0.5499 3.8108 H 1.1928 0.7029 3.4086 H -0.4861 1.1638 3.8369 O -0.1054 1.6558 1.2918 C -0.8178 1.9662 0.2193 O -1.6630 1.2138-0.3047 N -0.5783 3.2251-0.2508 C -1.1213 3.6182-1.5424 H -0.3779 3.4628-2.3412 C 0.4981 4.0671 0.2577 H 0.7465 3.7861 1.2809 B 0.7102-0.8471 1.0756 C 0.0292-2.3153 1.3902 H -0.1712-2.4653 2.4628 H 0.6788-3.1388 1.0662 H -0.9355-2.4616 0.8733 H -2.0135 3.0305-1.7630 H -1.3819 4.6831-1.5109 H 0.1637 5.1118 0.2378 H 1.3966 3.9694-0.3694 H -1.3065 0.0519 1.7830 O 0.6947-0.6547-0.4354 O 2.1183-0.6820 1.4429 C 2.9186-0.8335 0.2818 C 2.0027-0.2624-0.8610 C 2.0830 1.2687-0.9462 H 3.0387 1.5895-1.3806 H 1.2683 1.6358-1.5834 H 1.9792 1.7089 0.0467 C 2.3114-0.8538-2.2388 H 1.7266-0.3499-3.0184 H 3.3744-0.7127-2.4749 H 2.0886-1.9246-2.2702 C 4.2264-0.0635 0.4748 H 4.8186-0.5448 1.2627 H 4.8177-0.0615-0.4513 H 4.0303 0.9704 0.7753 C 3.2490-2.3225 0.0576 H 3.6681-2.7272 0.9860 H 2.3492-2.8904-0.1950 H 3.9826-2.4526-0.7489 Li -1.3151-0.6729-0.1895 O -3.1020-1.3371 0.6783 O -1.8395-1.4508-1.9473 C -1.1561-2.7003-2.0543 H -0.0813-2.5536-1.8917 H -1.5623-3.3465-1.2717 H -1.3409-3.1464-3.0433 C -1.4256-0.5142-2.9389 H -0.3598-0.2889-2.8212 H -1.6196-0.9191-3.9441 H -2.0085 0.3949-2.7738 C -4.1574-0.6266 0.0362 12

H -4.2227 0.3972 0.4313 H -3.9139-0.5987-1.0268 H -5.1130-1.1508 0.1920 C -3.3245-1.4825 2.0752 H -2.4594-2.0081 2.4845 H -3.4214-0.4967 2.5565 H -4.2410-2.0654 2.2535 C 1.1539 0.4057 2.0414 C 2.1173 0.3724 3.2236 H 1.7628-0.3560 3.9611 H 3.1105 0.0549 2.8846 H 2.1987 1.3534 3.7140 O 1.6721 1.5256 1.2069 C 0.8560 2.1819 0.4064 O -0.3568 1.9441 0.2661 N 1.4776 3.2116-0.2555 C 0.7712 3.8841-1.3331 H 0.9267 3.3718-2.2971 C 2.9299 3.3537-0.2659 H 3.3481 3.0120 0.6809 B 1.0775-1.0372 1.2434 C 0.2784-2.0788 2.2343 H 0.7699-2.1500 3.2160 H 0.2380-3.1002 1.8341 H -0.7640-1.7651 2.4166 H -0.2975 3.9141-1.1122 H 1.1508 4.9090-1.4189 H 3.1748 4.4127-0.4111 H 3.3787 2.7702-1.0848 H 0.1644 0.7305 2.3853 O 0.3497-0.9180-0.1002 O 2.4328-1.4717 0.8392 C 2.3882-2.0096-0.4673 C 1.2724-1.1531-1.1669 C 1.8328 0.1794-1.6913 H 2.4370 0.0192-2.5937 H 1.0029 0.8491-1.9413 H 2.4594 0.6507-0.9326 C 0.5549-1.8574-2.3213 H -0.2067-1.1893-2.7403 H 1.2715-2.1079-3.1147 H 0.0657-2.7794-1.9963 C 3.7711-1.8753-1.1120 H 4.4790-2.5297-0.5888 H 3.7407-2.1718-2.1698 H 4.1385-0.8472-1.0391 C 2.0202-3.5068-0.4211 H 2.7133-4.0110 0.2620 H 1.0041-3.6547-0.0467 H 2.0997-3.9698-1.4140 Li -1.2898 0.0558 0.0379 O -2.8837 1.0270 1.0988 O -2.1480 0.3430-1.8241 C -2.9427-0.6077-2.5160 H -2.3577-1.0942-3.3116 H -3.2568-1.3499-1.7820 H -3.8218-0.1166-2.9631 C -1.6467 1.3628-2.6747 H -1.0017 0.9306-3.4557 H -2.4779 1.9061-3.1532 H -1.0678 2.0353-2.0424 C -3.3188 2.2672 0.5617 H -2.5356 3.0283 0.6761 H -3.5107 2.0959-0.5006 H -4.2419 2.5968 1.0656 C -2.5429 1.1168 2.4748 H -2.1855 0.1283 2.7788 H -1.7446 1.8576 2.6211 H -3.4251 1.3974 3.0727 O -2.5482-1.7201 0.4398 C -1.9965-2.9921 0.1202 H -2.5347-3.4341-0.7358 H -0.9528-2.8162-0.1259 H -2.0675-3.6686 0.9843 C -3.9041-1.8225 0.8443 H -4.5125-2.2790 0.0444 H -3.9879-2.4478 1.7477 H -4.2554-0.8107 1.0495 C 0.2613-0.5217 1.8341 C -0.1574-1.9896 1.9976 H -0.9798-2.0183 2.7207 H -0.5152-2.4735 1.0816 H 0.6686-2.6017 2.3845 O 1.6499-0.4287 1.2834 C 2.0013-0.9569 0.1277 O 1.2469-1.6203-0.6182 N 3.3062-0.7276-0.1932 C 3.7735-1.0395-1.5384 H 4.8246-1.3460-1.4850 C 4.1223 0.2185 0.5643 H 3.8866 0.1551 1.6271 B -0.8557 0.5747 1.2496 C -2.1730 0.4138 2.2130 13

H -2.6824-0.5551 2.0824 H -2.9128 1.1992 2.0036 H -1.9156 0.4976 3.2816 H 3.1766-1.8503-1.9579 H 3.6956-0.1581-2.1945 H 3.9471 1.2491 0.2228 H 5.1763-0.0374 0.4089 H 0.4579-0.1430 2.8412 O -0.3221 1.9470 1.2429 O -1.1973 0.3322-0.2158 C -1.2329 1.5883-0.8979 C -0.2070 2.4514-0.0758 C 1.2365 2.2751-0.5862 H 1.3921 2.8051-1.5357 H 1.9193 2.6836 0.1670 H 1.4789 1.2222-0.7407 C -0.5319 3.9487-0.0676 H 0.2410 4.4832 0.4981 H -0.5552 4.3509-1.0901 H -1.4973 4.1349 0.4120 C -0.8558 1.3645-2.3627 H -1.6321 0.7671-2.8589 H -0.7741 2.3243-2.8892 H 0.0999 0.8371-2.4508 C -2.6621 2.1455-0.8216 H -3.3558 1.4006-1.2317 H -2.9401 2.3521 0.2150 H -2.7577 3.0704-1.4038 Li -0.5385-1.2886-0.5155 O -1.8675-2.5781-0.9526 C -1.6002-3.9747-0.9909 H -1.6149-4.3954 0.0262 H -2.3505-4.4879-1.6098 H -0.6053-4.0984-1.4268 C -3.1259-2.2561-0.3547 H -3.9450-2.6594-0.9673 H -3.1797-2.6765 0.6602 H -3.1720-1.1667-0.3020 C -0.8588-0.2013 2.1771 C 0.3458 0.3216 2.9636 H 0.6854-0.4743 3.6359 H 1.1807 0.6037 2.3172 H 0.0772 1.1950 3.5750 O -1.6220 0.9490 1.5999 C -1.0830 1.8283 0.7851 O 0.1051 1.8423 0.4017 N -1.9692 2.7918 0.3812 C -1.5697 3.6935-0.6896 H -2.1905 4.5944-0.6372 C -3.4060 2.6393 0.6000 H -3.5909 2.1910 1.5767 B -0.6460-1.4952 1.1651 C -0.0878-2.7214 2.1068 H 0.8090-2.4774 2.6958 H 0.1498-3.6177 1.5161 H -0.8683-3.0183 2.8257 H -0.5211 3.9722-0.5668 H -1.7044 3.2301-1.6809 H -3.8585 2.0006-0.1730 H -3.8679 3.6322 0.5622 H -1.6004-0.5465 2.9052 O -1.9124-1.8905 0.5047 O 0.2608-1.1672-0.0190 C -0.2975-1.7576-1.1959 C -1.8404-1.7360-0.8965 C -2.4937-0.4036-1.3179 H -2.6000-0.3351-2.4094 H -3.4871-0.3498-0.8591 H -1.9077 0.4518-0.9768 C -2.6125-2.8766-1.5700 H -3.6800-2.7760-1.3382 H -2.4896-2.8453-2.6620 H -2.2727-3.8482-1.1997 C 0.1161-0.9326-2.4155 H 1.1976-1.0182-2.5760 H -0.3951-1.3012-3.3141 H -0.1327 0.1240-2.2828 C 0.2518-3.1840-1.3543 H 1.3485-3.1452-1.3372 H -0.0900-3.8249-0.5386 H -0.0691-3.6270-2.3057 Li 1.2270 0.3895-0.0097 O 2.9608-0.0983 0.8445 O 2.2869 1.2944-1.5330 C 3.7666 0.9373 1.3858 H 3.4783 1.1436 2.4279 H 4.8301 0.6539 1.3525 H 3.5946 1.8237 0.7692 C 3.0804-1.3372 1.5398 H 4.1101-1.7168 1.4524 H 2.8238-1.2042 2.5997 H 2.3657-2.0201 1.0795 C 3.3842 0.6568-2.1702 H 3.7942-0.0563-1.4522 H 3.0502 0.1292-3.0770 H 4.1488 1.3995-2.4477 C 1.6352 2.2348-2.3759 H 1.2571 1.7383-3.2829 H 0.8053 2.6442-1.7987 H 2.3340 3.0353-2.6652 14

C 0.8720 0.3152-2.1919 C -0.5452 0.5167-2.7309 H -0.7457-0.2701-3.4664 H -1.3216 0.4544-1.9658 H -0.6499 1.4895-3.2339 O 1.3607 1.5837-1.5702 C 0.7852 2.0989-0.5048 O -0.2397 1.6644 0.0487 N 1.4141 3.2315-0.0491 C 1.0348 3.7414 1.2609 H 1.3185 4.7980 1.3209 C 2.7545 3.5894-0.5068 H 2.8616 3.3612-1.5675 B 1.2099-1.0764-1.3554 C 0.8124-2.3074-2.3725 H -0.2506-2.3116-2.6601 H 1.0350-3.2911-1.9341 H 1.3926-2.2406-3.3074 H -0.0446 3.6492 1.3970 H 1.5451 3.1919 2.0692 H 3.5237 3.0375 0.0536 H 2.8971 4.6647-0.3494 H 1.5460 0.2786-3.0539 O 2.6447-1.1331-0.9921 O 0.5054-1.1550-0.0128 C 1.4355-1.6450 0.9566 C 2.8215-1.1373 0.4083 C 3.1613 0.2801 0.9127 H 3.4888 0.2624 1.9615 H 3.9718 0.6795 0.2932 H 2.3019 0.9467 0.8383 C 4.0044-2.0502 0.7565 H 4.9284-1.6032 0.3690 H 4.1061-2.1691 1.8446 H 3.8845-3.0361 0.2981 C 1.0737-1.0973 2.3376 H 0.1201-1.5229 2.6717 H 1.8499-1.3673 3.0659 H 0.9724-0.0098 2.3142 C 1.3837-3.1825 1.0090 H 0.3726-3.5122 1.2696 H 1.6569-3.6127 0.0425 H 2.0722-3.5681 1.7709 Li -1.1209-0.0747 0.0150 O -2.3988-1.6632-0.6748 O -1.9136-0.0740 1.9655 C -2.6997-1.0655 2.5981 H -3.5886-0.6119 3.0661 H -3.0141-1.7697 1.8263 H -2.1149-1.5892 3.3713 C -1.5339 0.9686 2.8508 H -2.4307 1.4770 3.2421 H -0.9500 0.5654 3.6921 H -0.9249 1.6631 2.2711 C -3.0744-1.6705-1.9261 H -3.9688-2.3119-1.8695 H -3.3614-0.6393-2.1377 H -2.4103-2.0439-2.7183 C -1.9592-2.9646-0.2985 H -1.4778-2.8643 0.6726 H -2.8233-3.6462-0.2308 H -1.2265-3.3497-1.0159 O -3.0240 1.1243-0.5231 C -4.1660 0.8070 0.2521 H -4.1764-0.2775 0.3704 H -4.1080 1.2843 1.2429 H -5.0839 1.1423-0.2584 C -2.9227 2.5152-0.7862 H -2.7865 3.0772 0.1507 H -2.0470 2.6587-1.4198 H -3.8298 2.8732-1.3001 C -0.9461-2.4972-1.4666 B -1.2670-1.0505-0.7520 O -2.3056-0.2363-1.4108 C -3.4947-0.3120-0.6398 C -4.3411-1.5043-1.1258 C 0.1670-0.2001-0.6544 O -0.0741 1.2406-0.4585 C 0.8379 1.9670 0.1674 N 0.4770 3.2641 0.3349 C -0.8321 3.7819-0.0588 C 1.1357-0.3568-1.8270 O 1.9409 1.5180 0.5669 C 1.3118 4.1794 1.0983 O -1.7766-1.2747 0.6405 C -2.9673-0.5247 0.8299 C -3.9239-1.3130 1.7299 C -4.2984 0.9764-0.8353 C -2.6281 0.8079 1.5252 Li 2.4185-0.2474 0.2252 O 2.3436-1.9232 1.2657 C 1.2063-2.6497 1.7689 C 3.5484-2.3019 1.9253 15

O 4.1830-0.3517-0.5404 C 4.6701 0.8760-1.0839 C 4.4221-1.4732-1.3893 H 1.4276-1.4086-1.9223 H 0.6323-0.0657-2.7557 H 2.0445 0.2607-1.7365 H 0.8089 4.4559 2.0367 H -1.3406 3.0724-0.7112 H -0.6992-2.3907-2.5357 H -1.8169-3.1639-1.3959 H -0.1002-3.0295-0.9932 H 2.2670 3.7054 1.3278 H 1.4832 5.0935 0.5140 H -0.6909 4.7341-0.5867 H -1.4514 3.9597 0.8316 H 0.5800-0.5546 0.2951 H -3.5347 1.3753 1.7773 H -2.0839 0.5865 2.4529 H -1.9939 1.4198 0.8812 H -3.4937-1.3979 2.7366 H -4.8940-0.8024 1.8101 H -4.0857-2.3218 1.3381 H -4.6394 1.0397-1.8765 H -5.1794 0.9912-0.1785 H -3.6821 1.8558-0.6204 H -4.5064-1.3945-2.2044 H -3.8129-2.4460-0.9487 H -5.3148-1.5446-0.6188 H 5.5031-1.6249-1.5190 H 3.9744-2.3416-0.8996 H 3.9485-1.3168-2.3686 H 5.7643 0.8352-1.1799 H 4.2193 1.0588-2.0705 H 4.3703 1.6660-0.3924 H 4.3551-1.6981 1.5026 H 3.4668-2.1139 3.0062 H 3.7517-3.3711 1.7611 H 1.1195-2.4843 2.8521 H 0.3044-2.2885 1.2718 H 1.3449-3.7212 1.5684 C -0.3624-0.5187-0.9754 C 0.0730-0.7611-2.4157 H 0.2476-1.8312-2.5693 H -0.7339-0.4563-3.0929 H 0.9911-0.2142-2.6797 O -0.5328 0.9456-0.8247 C 0.4947 1.7529-0.6829 O 1.6715 1.3792-0.4684 N 0.1615 3.0696-0.7728 C 1.1323 4.1128-0.4887 H 0.8218 4.6889 0.3959 C -1.1972 3.5300-1.0499 H -1.8169 2.6981-1.3847 B -1.7982-1.2291-0.5300 C -1.7467-2.8402-0.8616 H -1.4670-3.0749-1.9025 H -2.7334-3.2930-0.6924 H -1.0452-3.3730-0.1986 H 2.1110 3.6677-0.3053 H 1.1998 4.8011-1.3427 H -1.1571 4.2994-1.8325 H -1.6434 3.9691-0.1464 H 0.4272-0.8190-0.2763 O -2.0457-1.0292 0.9371 O -2.9007-0.4930-1.1928 C -3.9349-0.2624-0.2542 C -3.1829-0.2042 1.1355 C -2.7245 1.2214 1.5028 H -3.5788 1.8727 1.7325 H -2.0857 1.1655 2.3945 H -2.1500 1.6603 0.6867 C -4.0022-0.7533 2.3104 H -3.4172-0.6652 3.2356 H -4.9359-0.1871 2.4362 H -4.2453-1.8090 2.1585 C -4.6582 1.0371-0.6243 H -5.1580 0.9105-1.5931 H -5.4166 1.2939 0.1285 H -3.9491 1.8674-0.7086 C -4.9530-1.4189-0.3172 H -5.2910-1.5228-1.3554 H -4.4918-2.3607-0.0074 H -5.8246-1.2277 0.3235 Li 2.3157-0.2746 0.0646 O 2.6470-2.0669-0.6187 O 4.3107 0.1767 0.0610 C 5.3441-0.7464 0.3715 H 5.7431-0.5545 1.3800 H 4.9016-1.7438 0.3282 H 6.1641-0.6636-0.3583 C 4.7434 1.5314 0.1250 H 5.0841 1.7742 1.1441 H 5.5703 1.7005-0.5814 H 3.8824 2.1450-0.1437 C 1.7636-3.1307-0.2500 H 2.3304-4.0694-0.1606 H 1.3256-2.8553 0.7114 H 0.9671-3.2412-0.9932 C 3.2397-2.2504-1.8988 H 3.8708-1.3767-2.0831 H 3.8523-3.1651-1.9059 16

H 2.4647-2.3211-2.6731 O 1.7591-0.5735 1.9505 C 2.8517-0.2777 2.8083 H 3.6970-0.8900 2.4854 H 3.1216 0.7885 2.7429 H 2.5941-0.5219 3.8496 C 0.5593 0.1192 2.3391 H 0.6914 1.2006 2.1872 H -0.2701-0.2609 1.7352 H 0.3536-0.0807 3.4007 C -0.3389-0.3834-0.3709 C -0.1950 0.0393-1.8246 H 0.0403-0.8483-2.4218 H 0.6534 0.7195-1.9157 H -1.0900 0.5283-2.2364 O -1.4503-1.3639-0.2870 C -2.7012-0.9607-0.4398 O -3.0477 0.2390-0.5608 N -3.6069-1.9721-0.4170 C -5.0166-1.7149-0.6761 H -5.6239-2.2078 0.0943 C -3.2194-3.3798-0.3581 H -2.1996-3.4767 0.0135 B 1.0361-0.9708 0.3491 C 0.6323-1.8546 1.6723 H -0.0520-1.3095 2.3456 H 1.5083-2.1202 2.2803 H 0.1267-2.7941 1.3972 H -5.2059-0.6410-0.6615 H -5.3036-2.1210-1.6576 H -3.2881-3.8392-1.3552 H -3.9072-3.9036 0.3173 H -0.6073 0.4366 0.3021 O 1.8973-1.6594-0.6294 O 1.8279 0.2640 0.7197 C 3.1487 0.1749 0.1967 C 3.2456-1.2973-0.3948 C 4.0112-1.3883-1.7208 H 5.0478-1.0437-1.6031 H 4.0288-2.4343-2.0512 H 3.5251-0.7927-2.5000 C 3.8946-2.2946 0.5874 H 3.7716-3.3046 0.1784 H 4.9667-2.0923 0.7142 H 3.4165-2.2617 1.5686 C 3.3330 1.2579-0.8828 H 3.1213 2.2396-0.4396 H 4.3608 1.2703-1.2674 H 2.6552 1.0956-1.7259 C 4.1532 0.4609 1.3216 H 4.0259 1.4952 1.6679 H 3.9877-0.2075 2.1715 H 5.1871 0.3382 0.9700 Li -1.9444 1.6380-0.1283 O -0.9217 3.0773-0.8121 C 0.5088 3.0648-0.7040 H 0.8474 3.9844-0.2043 H 0.8022 2.1849-0.1263 H 0.9559 3.0033-1.7042 C -1.4069 4.1241-1.6441 H -2.4987 4.0532-1.6614 H -1.1066 5.1018-1.2395 H -1.0114 4.0129-2.6643 O -1.8809 1.8011 1.8205 C -2.4477 0.6576 2.4678 H -3.4247 0.4868 2.0109 H -1.8074-0.2216 2.3232 H -2.5614 0.8591 3.5426 C -0.5996 2.1496 2.3683 H 0.1458 1.3711 2.1554 H -0.3032 3.0865 1.8916 H -0.6935 2.3002 3.4530 C -0.3351 0.6297-0.4202 C -0.4653 0.3619-1.9122 H -1.0970 1.1356-2.3615 H -0.9623-0.5976-2.0640 H 0.5095 0.3317-2.4201 O 0.4052 1.9146-0.2822 C 1.7089 1.9514-0.4832 O 2.4303 0.9426-0.6545 N 2.2307 3.2089-0.4427 C 3.6355 3.4401-0.7411 H 4.0650 4.1073 0.0181 C 1.4009 4.4075-0.3524 H 0.4050 4.1516 0.0081 B -1.7570 0.7010 0.4418 C -1.5276 1.4642 1.8865 H -1.0373 0.8097 2.6262 H -2.4811 1.7715 2.3354 H -0.9141 2.3759 1.8000 H 4.1746 2.4919-0.7427 H 3.7458 3.9187-1.7261 17

H 1.3171 4.8913-1.3371 H 1.8735 5.1118 0.3441 H 0.2880-0.1302 0.0613 O -2.8329 1.2740-0.3929 O -2.1964-0.7297 0.6604 C -3.5005-0.9321 0.1290 C -4.0210 0.5302-0.1918 C -4.8757 0.6265-1.4613 H -5.7673-0.0114-1.3855 H -5.2028 1.6653-1.5950 H -4.3019 0.3322-2.3457 C -4.8406 1.1304 0.9703 H -4.9812 2.2000 0.7738 H -5.8259 0.6515 1.0496 H -4.3263 1.0190 1.9273 C -3.4107-1.8107-1.1328 H -2.9048-2.7500-0.8765 H -4.4085-2.0537-1.5202 H -2.8497-1.3084-1.9254 C -4.3494-1.6866 1.1615 H -3.9340-2.6926 1.3091 H -4.3445-1.1697 2.1255 H -5.3883-1.7889 0.8184 Li 2.0870-0.8374-0.1923 O 1.1801-2.3251-1.0702 O 3.9248-1.6675-0.1697 C 3.9153-2.8952 0.5539 H 3.6666-2.7093 1.6078 H 3.1449-3.5237 0.1018 H 4.8967-3.3869 0.4787 C 4.8754-0.7437 0.3527 H 4.6621-0.5400 1.4128 H 5.8928-1.1512 0.2555 H 4.7714 0.1751-0.2270 C -0.1570-2.8105-0.9033 H -0.1292-3.8506-0.5436 H -0.6769-2.1625-0.1936 H -0.6890-2.7731-1.8621 C 1.8324-2.8852-2.2039 H 2.8451-2.4756-2.2289 H 1.8751-3.9824-2.1187 H 1.2903-2.6148-3.1217 O 1.8195-0.9260 1.7850 C 1.8927 0.3710 2.3844 H 2.8039 0.8397 2.0047 H 1.0202 0.9738 2.1144 H 1.9470 0.2717 3.4786 C 0.6931-1.6834 2.2500 H -0.2533-1.2117 1.9604 H 0.7721-2.6698 1.7848 H 0.7439-1.7836 3.3441 C -0.4919-0.1727-0.9057 C -0.9047 0.4872-2.2146 H -1.0303-0.2926-2.9744 H -0.0929 1.1407-2.5485 H -1.8350 1.0687-2.1494 O -1.4800-1.2161-0.5628 C -2.6937-0.8818-0.1558 O -3.0688 0.2967 0.0509 N -3.5074-1.9466 0.0595 C -4.9060-1.7539 0.4165 H -5.1509-2.3846 1.2812 C -3.1117-3.3201-0.2436 H -2.0270-3.3943-0.3176 B 1.0066-0.8445-0.9270 C 1.1425-1.9273-2.1493 H 0.3159-2.6572-2.1137 H 2.0735-2.5106-2.1207 H 1.1006-1.4389-3.1370 H -5.0838-0.7068 0.6641 H -5.5562-2.0453-0.4219 H -3.5650-3.6503-1.1899 H -3.4695-3.9727 0.5626 H -0.4408 0.5196-0.0612 O 1.9417 0.3273-0.9990 O 1.3034-1.4068 0.4202 C 2.6714-1.1768 0.7205 C 3.1301-0.0224-0.3044 C 3.6807 1.2395 0.3773 H 4.6144 1.0258 0.9138 H 3.8897 1.9928-0.3931 H 2.9679 1.6663 1.0894 C 4.1899-0.4860-1.3237 H 4.3977 0.3454-2.0090 H 5.1273-0.7757-0.8305 H 3.8272-1.3289-1.9154 C 2.7661-0.7701 2.2005 H 2.3565-1.5844 2.8117 H 3.8065-0.5960 2.5050 H 2.1875 0.1333 2.4090 C 3.4595-2.4905 0.5579 H 3.0474-3.2316 1.2540 H 3.3643-2.8875-0.4553 H 4.5256-2.3525 0.7850 Li -1.8600 1.6339 0.3359 O -1.1148 3.1910-0.4764 C 0.2368 3.2860-0.9522 H 0.7455 4.1159-0.4407 18

H 0.7444 2.3398-0.7485 H 0.2317 3.4667-2.0353 C -1.8997 4.3292-0.8126 H -2.9049 4.1677-0.4108 H -1.4660 5.2373-0.3685 H -1.9524 4.4454-1.9048 O -1.0415 1.4147 2.0834 C -0.9745 0.0442 2.5239 H -1.9874-0.3562 2.4405 H -0.2741-0.5286 1.9003 H -0.6486 0.0202 3.5734 C 0.2463 2.0342 2.1123 H 0.9125 1.5469 1.3907 H 0.1026 3.0834 1.8437 H 0.6781 1.9598 3.1204 C 0.2068 0.5877 1.1024 C -0.1884 0.3523 2.5547 H 0.1353 1.2084 3.1569 H 0.3432-0.5286 2.9281 H -1.2690 0.2061 2.6887 O -0.3521 1.8942 0.6852 C -1.6317 2.0014 0.3828 O -2.4446 1.0496 0.3879 N -1.9954 3.2612 0.0170 C -3.3949 3.5967-0.1968 H -3.4976 4.1568-1.1356 C -1.0700 4.3905 0.0767 H -0.0411 4.0401-0.0083 B 1.8291 0.6317 0.8289 C 2.5451 1.6377 1.9136 H 1.9945 2.5922 1.9726 H 3.5828 1.8967 1.6631 H 2.5554 1.2093 2.9293 H -3.9891 2.6835-0.2485 H -3.7699 4.2250 0.6254 H -1.1877 4.9425 1.0213 H -1.2964 5.0677-0.7559 H -0.2292-0.1661 0.4434 O 2.2968-0.7948 0.8714 O 2.0972 1.0058-0.5905 C 3.2402 0.2953-1.0419 C 3.4286-0.9009 0.0195 C 3.4387-2.3034-0.6096 H 4.3172-2.4385-1.2543 H 3.4837-3.0488 0.1946 H 2.5448-2.4985-1.2089 C 4.7128-0.7822 0.8654 H 4.7250-1.6050 1.5912 H 5.6144-0.8522 0.2424 H 4.7388 0.1575 1.4196 C 2.9616-0.1839-2.4767 H 2.7618 0.6944-3.1038 H 3.8226-0.7216-2.8949 H 2.0883-0.8380-2.5228 C 4.4477 1.2495-1.1119 H 4.2120 2.0585-1.8146 H 4.6607 1.6967-0.1387 H 5.3491 0.7307-1.4665 Li -2.0492-0.7542 0.1269 O -1.5240-2.2417 1.3278 O -3.8016-1.5499-0.4820 C -3.5997-2.8168-1.1012 H -2.9678-2.7047-1.9931 H -3.0950-3.4520-0.3695 H -4.5668-3.2603-1.3815 C -4.4128-0.6145-1.3692 H -3.7794-0.4710-2.2567 H -5.4052-0.9782-1.6751 H -4.4988 0.3259-0.8225 C -0.2465-2.7972 1.6670 H -0.2193-3.8575 1.3733 H 0.5298-2.2270 1.1526 H -0.0826-2.7155 2.7495 C -2.5605-2.6815 2.1983 H -3.4919-2.2326 1.8448 H -2.6426-3.7795 2.1741 H -2.3500-2.3573 3.2279 O -1.1614-0.9275-1.6441 C -0.6776 0.2883-2.2416 H -1.5017 1.0051-2.1916 H 0.2026 0.6626-1.7017 H -0.4130 0.0944-3.2915 C -0.1360-1.9198-1.5675 H 0.6934-1.5590-0.9484 H -0.5863-2.8062-1.1131 H 0.2315-2.1619-2.5756 C 0.5081-2.4582-0.6330 B -0.3533-1.2812 0.0844 O -0.8145-0.1987-0.9068 C -2.2244-0.3345-1.0975 C -2.4805-1.3397-2.2293 C 0.5578-0.5623 1.3108 O 2.0220-0.6791 1.0570 C 2.5488 0.0018 0.0538 N 3.7974-0.4111-0.2937 19

C 4.3447-1.6770 0.1907 C 0.3666-1.2774 2.6413 O 1.9835 0.9673-0.5040 C 4.4358 0.1493-1.4779 O -1.6371-1.7815 0.6300 C -2.6823-0.8901 0.2913 C -4.0088-1.6486 0.2542 C -2.8134 1.0226-1.4795 C -2.7688 0.2284 1.3498 Li 0.1517 1.2013-0.3537 O -0.1840 3.0287 0.2166 C 0.8897 3.9279-0.0642 C -1.3075 3.6846 0.7953 H -0.6754-1.1648 2.9539 H 0.5597-2.3503 2.5237 H 1.0310-0.8761 3.4194 H 4.2715-0.4978-2.3533 H 4.0253-1.8597 1.2170 H 1.3797-2.0705-1.1851 H -0.1124-3.0076-1.3549 H 0.8891-3.1897 0.0972 H 4.0246 1.1379-1.6858 H 5.5143 0.2289-1.2962 H 5.4381-1.6133 0.1565 H 4.0129-2.5144-0.4404 H 0.3802 0.5151 1.4894 H -3.6001 0.9186 1.1518 H -2.9184-0.2296 2.3342 H -1.8339 0.7992 1.3803 H -4.2651-1.9909 1.2643 H -4.8187-1.0013-0.1105 H -3.9324-2.5250-0.3960 H -2.4514 1.3199-2.4723 H -3.9094 0.9693-1.5147 H -2.5283 1.7979-0.7620 H -1.9306-1.0160-3.1211 H -2.1276-2.3330-1.9388 H -3.5490-1.3982-2.4729 H -1.7262 4.4170 0.0892 H -2.0521 2.9207 1.0249 H -1.0069 4.1984 1.7204 H 0.5653 4.6863-0.7922 H 1.2146 4.4250 0.8618 H 1.7070 3.3296-0.4708 C 0.4890-1.3650 1.1058 C 0.2522-2.4791 2.1151 H -0.7899-2.4449 2.4439 H 0.4127-3.4562 1.6432 H 0.9158-2.3916 2.9879 O 1.9523-1.4523 0.8320 C 2.5068-0.4998 0.1024 O 1.9750 0.6038-0.1252 N 3.7557-0.8121-0.3498 C 4.4105 0.0832-1.2941 H 4.2009-0.2182-2.3327 C 4.2552-2.1846-0.3235 H 3.8959-2.7007 0.5670 B -0.4291-1.5266-0.2922 C 0.4080-2.2669-1.4772 H 1.2691-1.6792-1.8360 H -0.2420-2.4470-2.3459 H 0.7982-3.2445-1.1521 H 4.0545 1.1034-1.1424 H 5.4938 0.0419-1.1289 H 5.3508-2.1527-0.3076 H 3.9257-2.7395-1.2148 H 0.3475-0.3938 1.6097 O -1.7033-2.2360-0.0181 O -0.9068-0.1279-0.6906 C -2.3202-0.1532-0.8701 C -2.7578-1.3015 0.1022 C -2.8463-0.8063 1.5585 H -3.6748-0.1003 1.7043 H -3.0008-1.6703 2.2150 H -1.9103-0.3198 1.8462 C -4.0786-1.9711-0.2791 H -4.3212-2.7470 0.4574 H -4.8981-1.2388-0.2960 H -4.0025-2.4442-1.2626 C -2.8915 1.2244-0.5332 H -2.5834 1.9510-1.2941 H -3.9887 1.1934-0.5126 H -2.5322 1.5744 0.4412 C -2.6263-0.4950-2.3359 H -2.1069 0.2225-2.9831 H -2.2664-1.5014-2.5687 H -3.7027-0.4431-2.5440 Li 0.1631 1.1018 0.1112 O 0.0041 2.1939 1.8350 O 0.1595 2.7417-1.0177 C -0.5484 3.9578-0.8555 H -1.5596 3.8815-1.2831 H -0.6195 4.1399 0.2199 H -0.0099 4.7830-1.3477 C 0.2685 2.3211-2.3732 H -0.7311 2.1803-2.8099 H 0.8285 3.0672-2.9581 H 0.7959 1.3658-2.3605 C 1.3299 2.6927 2.0144 H 1.9671 1.9281 2.4812 H 1.7148 2.9245 1.0201 H 1.3077 3.5942 2.6458 20

C -0.6040 1.8177 3.0647 H -1.6352 1.5349 2.8440 H -0.0744 0.9632 3.5127 H -0.5921 2.6649 3.7671 H 3.5588-2.6589-1.3338 H 2.5871-1.4507-2.2021 H 4.2985-1.1180-1.8468 H -1.2281 3.5809 1.8863 H -1.4605 4.7322 0.5322 H -2.3663 3.1740 0.5599 H -0.4001 4.1435-1.6141 H 0.3643 2.5128-1.6948 H -1.4167 2.6545-1.5959 C -0.0703-2.0005-1.3053 B 0.6211-1.1921-0.0688 O 1.8974-1.7214 0.4528 C 2.9803-0.9916-0.0995 C 3.3816-1.5851-1.4639 C -0.4129-1.2483 1.2599 O -1.8545-1.4377 0.9194 C -2.4919-0.5093 0.2301 N -3.7107-0.9040-0.2288 C -4.1219-2.3059-0.2261 C -0.2977-0.2831 2.4449 O -2.0549 0.6459 0.0398 C -4.4615-0.0251-1.1158 O 1.0153 0.2182-0.5299 C 2.3992 0.4601-0.2405 C 3.0106 1.2787-1.3792 C 4.1796-1.0877 0.8464 C 2.5058 1.2668 1.0629 Li -0.2929 1.0960 0.3178 O -0.3356 3.0288 0.1428 C -0.4610 3.0971-1.2822 C -1.4189 3.6694 0.8127 H 0.6893-0.4212 2.8971 H -0.4039 0.7890 2.2163 H -1.0588-0.5084 3.2039 H -5.5324-0.1565-0.9205 H -3.6720-2.8302 0.6167 H -0.4196-2.9983-0.9959 H 0.6246-2.1435-2.1434 H -0.9458-1.4644-1.7093 H -4.1810 1.0129-0.9322 H -4.2626-0.2692-2.1709 H -3.8203-2.8029-1.1601 H -5.2140-2.3462-0.1387 H -0.1915-2.2403 1.6635 H 3.5408 1.5766 1.2541 H 1.8881 2.1705 0.9792 H 2.1650 0.6745 1.9149 H 2.5964 2.2955-1.3766 H 4.0984 1.3565-1.2519 H 2.8010 0.8169-2.3485 H 4.5419-2.1226 0.8676 H 4.9986-0.4402 0.5040 H 3.9015-0.8007 1.8653 C 0.1337-1.5493-1.4773 C 0.0588-0.3888-2.4606 H -0.9703-0.3321-2.8334 H 0.3059 0.5687-1.9942 H 0.7333-0.5327-3.3173 O 1.5661-1.8547-1.1756 C 2.2467-1.0870-0.3462 O 1.9065 0.0559 0.0149 N 3.4253-1.6455 0.0645 C 4.1965-0.9812 1.1060 H 5.2594-1.2048 0.9563 C 3.6989-3.0691-0.1177 H 3.2856-3.4144-1.0655 B -0.8543-1.5088-0.1462 C -0.2939-2.5354 1.0007 H -0.1369-3.5496 0.5996 H -0.9793-2.6277 1.8549 H 0.6742-2.2024 1.4134 H 4.0391 0.0972 1.0515 H 3.8997-1.3344 2.1065 H 3.2617-3.6625 0.6995 H 4.7854-3.2140-0.1213 H -0.1429-2.4633-2.0121 O -1.0260-0.1179 0.4540 O -2.2058-1.7854-0.6852 C -3.1711-1.0024-0.0109 C -2.3868 0.3096 0.3869 C -2.4734 1.4174-0.6733 H -3.4853 1.8345-0.7483 H -1.7927 2.2273-0.3789 H -2.1747 1.0385-1.6548 C -2.7887 0.9069 1.7400 H -2.1782 1.7959 1.9401 H -3.8474 1.1991 1.7358 H -2.6281 0.1883 2.5490 C -4.3478-0.7460-0.9587 H -4.8445-1.6982-1.1805 H -5.0819-0.0691-0.4999 21

H -4.0044-0.3112-1.9029 C -3.7036-1.7676 1.2172 H -4.0759-2.7409 0.8771 H -2.9144-1.9402 1.9526 H -4.5242-1.2243 1.7045 Li 0.3148 1.0523 0.0257 O 0.7368 2.7377-1.1889 O 0.4646 2.0865 1.7358 C 0.0738 3.1797-2.3699 H 0.3654 4.2157-2.5990 H 0.3306 2.5299-3.2196 H -0.9993 3.1260-2.1806 C 2.1547 2.7668-1.3391 H 2.4651 2.1016-2.1578 H 2.4898 3.7944-1.5486 H 2.5851 2.4054-0.4048 C 1.2357 3.2589 1.9270 H 1.0354 3.9148 1.0764 H 0.9491 3.7589 2.8654 H 2.3103 3.0155 1.9661 C 0.6541 1.1219 2.7712 H 0.3307 1.5403 3.7366 H 0.0461 0.2581 2.4990 H 1.7142 0.8330 2.8261 H -1.1585-1.6537 3.5627 H -3.6466-2.8774-1.9479 H -0.8573-4.0045-0.0387 H 0.4368 1.9160 2.7440 H -0.9536 1.8371 1.6846 H 0.5463 2.6253 1.1279 H -3.6891-1.2231-1.2771 H -2.5400-1.6277-2.5822 H -0.4884-3.3945-1.6732 H -1.9680-4.3555-1.3884 H 0.9129-1.6323 2.2095 H 3.3251-2.1390-0.7745 H 3.3355-2.0156 1.0042 H 1.7889-2.1224 0.1277 H 4.8458-0.0762 0.6355 H 4.6048 0.0566-1.1242 H 4.2303 1.4391-0.0562 H 1.0160-0.0700-3.0447 H 2.7170-0.5361-2.8071 H 1.4131-1.5310-2.1082 H 1.1666 2.1703-2.0187 H 2.0878 2.4115-0.5050 H 2.9300 1.9373-2.0026 H -1.8951 4.6602-1.2477 H -1.0188 4.2257 0.2639 H -0.3686 3.7143-1.3237 H -2.9639 3.0913 1.0917 H -3.8985 3.4388-0.4046 H -3.6122 1.7365 0.1137 C 0.1500 1.7697 1.6941 B 0.7671 0.3480 1.1336 O 0.5185 0.2228-0.3824 C 1.7713 0.3357-1.0569 C 2.0116 1.8100-1.4162 C 0.0899-0.9813 1.9006 O -0.6331-1.9106 0.9792 C -1.6290-1.4754 0.2321 N -2.0716-2.4042-0.6649 C -1.2954-3.6070-0.9550 C -0.7932-0.7175 3.1173 O -2.1662-0.3489 0.3333 C -3.0412-2.0050-1.6763 O 2.2322 0.3559 1.2322 C 2.7770-0.1745 0.0319 C 4.2021 0.3485-0.1444 C 1.7277-0.5067-2.3314 C 2.8040-1.7147 0.0938 Li -1.0856 1.0678-0.1900 O -1.9928 2.6601-0.6983 C -3.1927 2.7444 0.0732 C -1.2812 3.8951-0.7508 H -0.1972-0.1877 3.8718 H -1.6521-0.0896 2.8593 C 0.4213-1.8602 1.3903 C -0.0424-2.0746 2.8269 H 0.8320-2.0071 3.4869 H -0.7499-1.2937 3.1298 H -0.5099-3.0598 2.9682 O -0.7476-2.1666 0.4924 C -1.7877-1.3570 0.4235 O -1.8207-0.1874 0.8515 N -2.8756-1.9289-0.1803 C -4.0798-1.1550-0.4272 H -4.9401-1.6334 0.0622 C -2.8796-3.2796-0.7247 H -2.0311-3.8442-0.3393 B 1.2343-0.4331 1.0989 C 0.8932 0.7345 2.2012 H 1.2740 0.4290 3.1862 H -0.1788 0.9350 2.3358 H 1.3918 1.6816 1.9518 22

H -3.9540-0.1452-0.0351 H -4.2849-1.1046-1.5077 H -2.8261-3.2529-1.8243 H -3.8136-3.7804-0.4358 H 1.0804-2.6849 1.1071 O 2.6943-0.6683 1.0703 O 0.9219 0.0209-0.3255 C 2.1578 0.2884-0.9914 C 3.1329-0.7088-0.2775 C 2.9863-2.1356-0.8435 H 3.4368-2.2204-1.8415 H 3.4957-2.8311-0.1663 H 1.9311-2.4198-0.9111 C 4.6025-0.2915-0.3403 H 5.2196-1.0518 0.1540 H 4.9368-0.1968-1.3830 H 4.7571 0.6626 0.1734 C 1.9971 0.0519-2.4933 H 1.3215 0.8031-2.9206 H 2.9708 0.1365-2.9934 H 1.5867-0.9424-2.6947 C 2.5520 1.7556-0.7568 H 1.7256 2.3963-1.0919 H 2.7434 1.9346 0.3049 H 3.4499 2.0243-1.3275 Li -0.5214 1.0781 0.1873 O -1.0191 2.9239 0.8184 O -1.3005 1.3827-1.7081 C -0.0333 3.9192 1.0702 H -0.4994 4.9163 1.0885 H 0.4676 3.7254 2.0289 H 0.6968 3.8608 0.2596 C -2.0093 2.8642 1.8421 H -1.5363 2.6810 2.8175 H -2.5741 3.8085 1.8757 H -2.6676 2.0278 1.5977 C -2.3509 2.2873-2.0018 H -2.2051 3.1605-1.3620 H -2.3216 2.5829-3.0628 H -3.3292 1.8273-1.7855 C -1.3903 0.1728-2.4523 H -1.2227 0.3702-3.5225 H -0.6154-0.4880-2.0637 H -2.3811-0.2846-2.3182 C -4.2990-0.6221 0.4075 C -3.1006-1.1613-0.3923 C -3.5884-2.2013-1.3985 O -2.1769-1.7823 0.5052 B -1.2619-0.7765 0.9619 O -1.4234 0.4029 0.0990 C -2.2451-0.0113-1.0218 C -1.3341-0.5203-2.1449 C -1.5306-0.4213 2.6880 H -2.3917 0.2465 2.5631 H -0.7848 0.1066 3.2915 H -1.8426-1.3395 3.1938 C 0.1531-1.1539 1.4184 O 1.2980-1.2745-0.4527 C 2.4787-0.8022-0.2378 O 2.6674 0.4076 0.0886 C 0.4920-2.4876 2.0059 N 3.5511-1.6707-0.3362 C 4.9154-1.1730-0.2975 C 3.3918-3.0102-0.8792 C -3.0563 1.1857-1.5101 Li 0.5711 0.7178-0.1266 O 0.6520 2.1185-1.5772 C 0.0208 3.3275-1.1850 C 1.9315 2.3291-2.1650 O 0.5393 2.0772 1.5235 C 1.7440 2.6686 1.9941 C -0.6196 2.7295 2.0211 H 5.3329-1.0765-1.3146 H -0.1863-3.2634 1.6367 H 1.5272-2.7384 1.7460 H 0.4310-2.4494 3.1038 H 2.3470-3.3135-0.8027 H 4.9321-0.1965 0.1889 H 5.5454-1.8769 0.2639 H 4.0246-3.7096-0.3151 H 3.6991-3.0483-1.9383 H 0.8313-0.3495 1.6992 H -1.9279-0.7971-3.0251 H -0.6386 0.2759-2.4286 H -0.7555-1.3856-1.8109 H -2.3921 1.9188-1.9826 H -3.7915 0.8610-2.2580 H -3.5878 1.6686-0.6836 H -4.1942-2.9542-0.8800 H -4.2084-1.7284-2.1719 H -2.7436-2.7048-1.8770 H -4.7212-1.4413 1.0006 H -3.9877 0.1774 1.0882 H -5.0774-0.2283-0.2583 H -0.1626 3.9647-2.0643 H -0.9248 3.0522-0.7154 H 0.6457 3.8718-0.4613 H 1.8316 2.9546-3.0657 H 2.6098 2.8083-1.4454 H 2.3294 1.3464-2.4230 H 1.7801 2.6355 3.0947 H 2.5650 2.0919 1.5660 H 1.8016 3.7214 1.6698 H -1.4784 2.2229 1.5797 H -0.6592 2.6553 3.1187 H -0.6120 3.7935 1.7329 23

C 0.2394-1.4054 2.0035 B 1.3616-1.1335 1.0170 C 2.2746-1.0241 2.6031 O 1.9318-2.1593 0.1962 C 2.0433-1.6418-1.1312 C 3.1849-2.3503-1.8547 O 1.4489 0.1259 0.2746 C 2.2979-0.1216-0.8709 C 3.7476 0.1760-0.4693 C -0.4666-0.4110 2.8865 O -1.6089-2.0088 0.8879 C -2.2539-1.0948 0.3007 N -3.5722-1.3704-0.0793 C -4.0588-2.7402-0.0700 C 0.7161-1.8825-1.8697 C 1.8815 0.7970-2.0129 O -1.8156 0.0776 0.0400 C -4.2779-0.4737-0.9757 Li -0.2498 0.9874 0.0684 O 0.0739 2.5597 1.2878 C 1.1513 2.6852 2.2059 C -1.1256 3.1890 1.7201 O -0.8316 2.3792-1.3972 C -1.6310 1.8998-2.4722 C -0.1198 3.5600-1.7239 H 0.0173-0.3518 3.8724 H -0.4830 0.5850 2.4406 H -1.4963-0.7460 3.0387 H -5.3587-0.5817-0.8130 H -3.5348-3.3067 0.7010 H 2.2761 0.0209 2.9263 H 3.2421-1.3102 2.1774 H 2.0851-1.6737 3.4625 H -3.9840 0.5578-0.7730 H -4.0702-0.7014-2.0382 H -3.8959-3.2354-1.0441 H -5.1375-2.7399 0.1386 H 0.1746-2.4369 2.3395 H 0.7780-1.5622-2.9183 H 0.4915-2.9539-1.8370 H -0.1041-1.3514-1.3751 H 2.9251-3.4056-1.9984 H 3.3561-1.8978-2.8409 H 4.1105-2.2987-1.2730 H 2.0827 1.8411-1.7464 H 2.4579 0.5530-2.9142 H 0.8181 0.6944-2.2404 H 3.8097 1.2026-0.0876 H 4.0811-0.5127 0.3125 H 4.4208 0.0809-1.3298 H -1.4593 2.7596 2.6771 H -0.9688 4.2723 1.8405 H -1.8718 2.9947 0.9464 H 1.4407 3.7424 2.3098 H 0.8664 2.2878 3.1916 H 1.9740 2.0942 1.7987 H 0.4666 3.8284-0.8418 H 0.5491 3.3864-2.5813 H -0.8197 4.3732-1.9737 H -0.9982 1.6625-3.3429 H -2.1295 1.0021-2.1044 H -2.3715 2.6610-2.7642 C -2.4690-0.1881-0.4301 C -3.1838 1.1712-0.3282 B -0.9077-0.0706-0.2725 O -0.2854 0.8885 0.4945 C 1.1478 0.7665 0.2722 C 1.5214 1.7969-0.7984 O -0.0165-0.9546-0.8396 C 1.2829-0.7153-0.2289 C 2.3719-0.9419-1.2706 C 1.4285-1.7227 0.9166 C 1.8800 1.0712 1.5738 C -3.0070-1.1585 0.6499 H -2.5338-2.1465 0.5781 H -4.0932-1.2902 0.5426 H -2.8177-0.7595 1.6564 H -2.9674 1.6462 0.6375 H -2.8571 1.8615-1.1173 H -4.2731 1.0472-0.4120 H -2.6835-0.6364-1.4120 H 3.3543-0.6884-0.8518 H 2.3822-1.9976-1.5653 H 2.2008-0.3340-2.1636 H 1.3267-2.7356 0.5116 H 2.4086-1.6306 1.3993 H 0.6493-1.5680 1.6718 H 1.2231 2.7921-0.4507 H 2.6017 1.7954-0.9853 H 1.0020 1.5848-1.7400 H 1.7192 2.1204 1.8468 H 1.5181 0.4405 2.3908 H 2.9578 0.9057 1.4488 O -2.070788-1.540203-0.370997 24

C -1.141784-2.379090-1.068708 O 0.560018-0.504401 1.013099 H -0.214768-2.472539-0.487856 C -2.359287-2.041814 0.937164 C 1.192582-0.050138-0.004934 N 2.571490-0.141623-0.040888 C 3.343524 0.465318-1.109017 H 4.121666-0.234516-1.448140 O 0.572105 0.468508-0.999256 C 3.332331-0.587067 1.111584 H 3.842534 0.261228 1.599649 H 2.659516-1.059832 1.828507 H 3.842772 1.386734-0.762437 Li -1.044745 0.037314 0.027412 O -1.979742 1.673474 0.408324 C -2.263107 2.153953-0.909148 C -0.993101 2.477618 1.066289 H -0.071721 2.498525 0.469468 H -2.813632-3.041133 0.866724 H -2.661523 3.178058-0.859809 H 4.100868-1.307627 0.794329 H 2.681300 0.708709-1.941143 H -3.069794-1.345626 1.392957 H -1.590490-3.369258-1.236677 H -3.017554 1.484817-1.333592 H -1.380749 3.497015 1.209705 H -1.349725 2.130766-1.520086 H -0.794203 2.006853 2.031699 H -1.436547-2.085254 1.532776 H -0.928449-1.890270-2.021799 C -0.1247 2.9136 0.6887 C -0.0224 1.4288 0.9850 O -1.4041 0.9089 0.4739 C -1.4641-0.3224 0.0194 N -2.7367-0.7597-0.2457 C -2.9505-2.0193-0.9403 O -0.4730-1.0682-0.1700 C -3.9004 0.1112-0.1493 Li 1.1165-0.0371 0.0427 O 2.4814-1.2507 0.7380 C 1.9816-1.6533 2.0125 C 2.4965-2.3278-0.1995 O 1.8659 0.4445-1.7377 C 2.6815 1.5634-1.3866 C 0.6916 0.8388-2.4485 C -0.1257 1.2146 2.4904 H -3.2090-1.8463-1.9979 H -3.7014 0.9263 0.5468 H 2.6270-2.4339 2.4434 H 1.9858-0.7658 2.6492 H 2.8408-1.9107-1.1489 H 3.1822-3.1172 0.1439 H 3.5405 1.1656-0.8386 H 3.0243 2.0822-2.2952 H 0.1351-0.0758-2.6656 H 0.0781 1.5036-1.8262 H -4.7534-0.4788 0.2105 H -4.1614 0.5348-1.1327 H -2.0454-2.6256-0.8872 H -3.7825-2.5576-0.4668 H 0.9531-2.0288 1.9125 H 1.4832-2.7358-0.3218 H 2.1177 2.2522-0.7428 H 0.9699 1.3475-3.3843 H 0.7698 3.4132 1.0902 H -0.1650 3.1321-0.3890 H -1.0092 3.3957 1.1580 H 0.7844 1.6052 2.9711 H -0.9940 1.7357 2.9484 H -0.2035 0.1492 2.7514 Li -0.1350 0.9488-0.3000 O -1.6742 0.1469-1.0558 C -2.3445-0.4531-0.1806 N -3.4570-1.1794-0.5154 C -3.7528-1.4540-1.9134 O -2.0720-0.4454 1.1029 C -0.8846 0.4221 1.6038 C -1.5404 1.7669 1.9022 C -0.5366-0.2771 2.9010 C -4.1604-2.0096 0.4541 O -0.1039 2.7568-1.0446 C -1.3377 3.3809-1.3744 C 0.9187 3.6772-0.6931 O 1.8059 0.5520-0.3977 C 2.2298-0.6768-1.0654 C 2.1346-1.7349 0.0911 C 0.7465-2.3683 0.2090 B 2.0028 0.3735 0.9817 O 2.3466-0.9218 1.2773 C 2.1669 1.5855 1.9700 C 3.6641-0.4347-1.5428 C 1.3090-0.9356-2.2512 C 3.2072-2.8175 0.0427 H -0.7878 2.4488 2.3240 H -2.3701 1.6939 2.6368 H -1.9421 2.2406 0.9954 25

H -3.2488-0.7222-2.5461 H -4.8375-1.3930-2.0703 H -3.4179-2.4656-2.1959 H -4.0446-1.5955 1.4561 H -3.7752-3.0419 0.4470 H -5.2246-2.0334 0.1877 H -1.7006 3.9870-0.5302 H -2.0447 2.5757-1.5869 H -1.2112 4.0248-2.2584 H 1.8143 3.0878-0.4883 H 0.6305 4.2488 0.2030 H 1.1055 4.3749-1.5242 H 1.5616-1.8972-2.7162 H 1.4431-0.1444-2.9986 H 0.2583-0.9527-1.9499 H 3.6746 0.4360-2.2081 H 4.0451-1.3035-2.0922 H 4.3287-0.2377-0.6939 H 1.3699 2.3267 1.8487 H 0.7163-2.9864 1.1127 H 0.5316-2.9999-0.6613 H -0.0184-1.5943 0.2989 H 3.1192-3.3952-0.8865 H 3.0709-3.4999 0.8892 H 4.2124-2.3897 0.1003 H 3.1236 2.0973 1.7735 H 2.1747 1.2576 3.0151 H 0.2159 0.3161 3.4349 H -1.4122-0.3838 3.5745 H -0.1073-1.2726 2.7330 O 1.7454 0.5389-0.4049 C 2.1837-0.6710-1.0898 C 1.2746-0.9140-2.2889 B 1.8912 0.3264 0.9829 O 2.2597-0.9725 1.2505 C 2.0903-1.7577 0.0429 C 0.7188-2.4342 0.1122 C 2.1121 1.5304 1.9744 C 3.6194-0.4066-1.5520 C 3.1901-2.8139-0.0084 Li -0.1483 1.0121-0.2728 O -1.6958 0.2674-1.0303 C -2.3275-0.4162-0.1891 N -3.4396-1.1309-0.5466 C -3.7789-1.2922-1.9525 O -2.0101-0.5130 1.0807 C -0.8192 0.3179 1.6306 C -1.4576 1.6596 1.9780 C -0.5050-0.4472 2.8989 C -4.0971-2.0513 0.3727 O -0.0790 2.8453-0.9241 C -1.2970 3.5322-1.1774 C 1.0200 3.7089-0.6729 H -0.7049 2.3015 2.4561 H -2.3100 1.5630 2.6819 H -1.8239 2.1886 1.0866 H -3.3071-0.5016-2.5374 H -4.8691-1.2365-2.0680 H -3.4394-2.2707-2.3297 H -3.9570-1.7178 1.4013 H -3.6944-3.0716 0.2694 H -5.1685-2.0743 0.1374 H -1.5748 4.1558-0.3137 H -2.0560 2.7646-1.3454 H -1.1942 4.1689-2.0696 H 1.8908 3.0693-0.5174 H 0.8339 4.3179 0.2255 H 1.1853 4.3740-1.5345 H 1.5353-1.8650-2.7709 H 1.4096-0.1076-3.0200 H 0.2218-0.9404-1.9949 H 3.6255 0.4746-2.2036 H 4.0156-1.2621-2.1116 H 4.2739-0.2146-0.6943 H 1.4079 2.3504 1.7977 H 0.6856-3.0731 1.0013 H 0.5447-3.0528-0.7764 H -0.0714-1.6876 0.1995 H 3.1357-3.3724-0.9520 H 3.0527-3.5184 0.8197 H 4.1831-2.3639 0.0806 H 3.1281 1.9359 1.8317 H 2.0259 1.2240 3.0222 H 0.2462 0.1040 3.4764 H -1.3964-0.5711 3.5469 H -0.0886-1.4393 2.6872 Conformers of 4b. C -0.1210-2.1150 1.4359 B 0.7582-0.7616 1.0833 O 2.1903-0.9373 1.3663 C 2.8922-1.1545 0.1566 C 2.9208-2.6592-0.1788 C 0.1559 0.5674 1.9613 O 0.1381 1.8302 1.1408 C -0.6580 1.9987 0.1013 N -0.4325 3.1781-0.5545 C 0.6628 4.0794-0.2184 C 1.1297 0.9460 3.0760 26

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