# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_page_first ? _publ_contact_author_name 'Harry W. Gibson' _publ_contact_author_address ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; _publ_contact_author_email hwgibson@vt.edu _publ_contact_author_fax 540-231-8517 _publ_contact_author_phone 540-231-5902 _publ_section_title ; Host folding during the formation of a taco complex ; loop_ _publ_author_name _publ_author_address 'Feihe Huang' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; 'Matthew Lam' ; Department of Chemistry and Biochemistry University of Delaware, Newark, DE, USA, 19716 ; 'Eric J. Mahan' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; 'Arnold L. Rheingold' ; Department of Chemistry and Biochemistry University of Delaware, Newark, DE, USA, 19716 ; 'Harry W. Gibson' ; Department of Chemistry Virginia Polytechnic Institute and State University Blacksburg, VA, USA, 24061 ; #===END data_1d _database_code_depnum_ccdc_archive 'CCDC 262641' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 O12' _chemical_formula_weight 594.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9525(3) _cell_length_b 11.2070(2) _cell_length_c 25.0146(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.6555(4) _cell_angle_gamma 90.00 _cell_volume 3043.06(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5999 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9803 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11411 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5107 _reflns_number_gt 3979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5107 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.680 _refine_ls_restrained_S_all 1.680 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.94820(17) 0.48577(18) 0.34587(8) 0.0418(5) Uani 1 1 d . . . O2 O 1.1131(2) 0.5137(2) 0.30305(11) 0.0727(8) Uani 1 1 d . . . O3 O 0.60881(15) 0.71937(17) 0.23153(8) 0.0383(5) Uani 1 1 d . . . O4 O 0.36591(17) 0.66530(18) 0.18727(8) 0.0409(5) Uani 1 1 d . . . O5 O 0.21006(18) 0.61144(19) 0.09015(8) 0.0469(5) Uani 1 1 d . . . O6 O 0.12681(19) 0.80661(18) 0.01159(8) 0.0454(5) Uani 1 1 d . . . O7 O 0.28790(18) 1.01472(17) -0.00135(8) 0.0402(5) Uani 1 1 d . . . O8 O 0.52677(18) 1.35897(17) 0.05588(8) 0.0415(5) Uani 1 1 d . . . O9 O 0.76585(17) 1.38904(17) 0.12199(8) 0.0386(5) Uani 1 1 d . . . O10 O 1.00277(17) 1.29278(17) 0.13104(8) 0.0407(5) Uani 1 1 d . . . O11 O 1.10038(16) 1.05813(17) 0.13967(8) 0.0378(5) Uani 1 1 d . . . O12 O 0.96750(16) 0.85580(17) 0.17201(8) 0.0378(5) Uani 1 1 d . . . C1 C 0.8018(2) 0.6269(2) 0.27267(11) 0.0323(6) Uani 1 1 d . . . H1A H 0.7620 0.5765 0.2956 0.039 Uiso 1 1 calc R . . C2 C 0.9292(2) 0.6239(2) 0.27358(10) 0.0315(6) Uani 1 1 d . . . C3 C 0.9904(2) 0.6988(2) 0.24095(11) 0.0348(6) Uani 1 1 d . . . H3A H 1.0775 0.6953 0.2423 0.042 Uiso 1 1 calc R . . C4 C 0.9209(2) 0.7787(2) 0.20630(11) 0.0319(6) Uani 1 1 d . . . C5 C 0.7933(2) 0.7826(2) 0.20457(11) 0.0326(6) Uani 1 1 d . . . H5A H 0.7464 0.8374 0.1812 0.039 Uiso 1 1 calc R . . C6 C 0.7339(2) 0.7064(2) 0.23692(10) 0.0321(6) Uani 1 1 d . . . C7 C 0.5378(2) 0.6386(3) 0.25980(11) 0.0383(7) Uani 1 1 d . . . H7A H 0.5612 0.6460 0.2993 0.046 Uiso 1 1 calc R . . H7B H 0.5512 0.5551 0.2491 0.046 Uiso 1 1 calc R . . C8 C 0.4045(2) 0.6746(3) 0.24385(11) 0.0408(7) Uani 1 1 d . . . H8A H 0.3513 0.6231 0.2631 0.049 Uiso 1 1 calc R . . H8B H 0.3935 0.7579 0.2554 0.049 Uiso 1 1 calc R . . C9 C 0.3382(3) 0.5473(3) 0.16958(13) 0.0461(8) Uani 1 1 d . . . H9A H 0.2629 0.5192 0.1836 0.055 Uiso 1 1 calc R . . H9B H 0.4070 0.4934 0.1832 0.055 Uiso 1 1 calc R . . C10 C 0.3186(3) 0.5457(3) 0.10904(13) 0.0476(8) Uani 1 1 d . . . H10A H 0.3905 0.5817 0.0950 0.057 Uiso 1 1 calc R . . H10B H 0.3099 0.4623 0.0960 0.057 Uiso 1 1 calc R . . C11 C 0.1775(3) 0.5979(3) 0.03348(12) 0.0484(8) Uani 1 1 d . . . H11A H 0.1455 0.5164 0.0253 0.058 Uiso 1 1 calc R . . H11B H 0.2511 0.6095 0.0150 0.058 Uiso 1 1 calc R . . C12 C 0.0818(3) 0.6872(3) 0.01363(13) 0.0479(8) Uani 1 1 d . . . H12A H 0.0439 0.6637 -0.0230 0.057 Uiso 1 1 calc R . . H12B H 0.0164 0.6855 0.0374 0.057 Uiso 1 1 calc R . . C13 C 0.2050(3) 0.8242(3) -0.02915(13) 0.0477(8) Uani 1 1 d . . . H13A H 0.1734 0.7778 -0.0618 0.057 Uiso 1 1 calc R . . H13B H 0.2892 0.7957 -0.0160 0.057 Uiso 1 1 calc R . . C14 C 0.2089(3) 0.9536(3) -0.04296(12) 0.0456(8) Uani 1 1 d . . . H14A H 0.2405 0.9637 -0.0780 0.055 Uiso 1 1 calc R . . H14B H 0.1249 0.9878 -0.0462 0.055 Uiso 1 1 calc R . . C15 C 0.3103(2) 1.1332(2) -0.00979(11) 0.0340(6) Uani 1 1 d . . . C16 C 0.2491(2) 1.2017(3) -0.05111(12) 0.0392(7) Uani 1 1 d . . . H16A H 0.1843 1.1687 -0.0757 0.047 Uiso 1 1 calc R . . C17 C 0.2845(3) 1.3195(3) -0.05569(11) 0.0398(7) Uani 1 1 d . . . H17A H 0.2434 1.3664 -0.0842 0.048 Uiso 1 1 calc R . . C18 C 0.3768(3) 1.3710(3) -0.02073(11) 0.0393(7) Uani 1 1 d . . . H18A H 0.3999 1.4518 -0.0251 0.047 Uiso 1 1 calc R . . C19 C 0.4358(2) 1.3016(2) 0.02151(11) 0.0342(6) Uani 1 1 d . . . C20 C 0.4040(2) 1.1834(2) 0.02722(10) 0.0331(6) Uani 1 1 d . . . H20A H 0.4449 1.1367 0.0558 0.040 Uiso 1 1 calc R . . C21 C 0.5620(3) 1.3079(3) 0.10788(11) 0.0387(7) Uani 1 1 d . . . H21A H 0.6032 1.2302 0.1043 0.046 Uiso 1 1 calc R . . H21B H 0.4882 1.2942 0.1260 0.046 Uiso 1 1 calc R . . C22 C 0.6491(3) 1.3928(3) 0.14091(12) 0.0386(7) Uani 1 1 d . . . H22A H 0.6156 1.4749 0.1376 0.046 Uiso 1 1 calc R . . H22B H 0.6580 1.3695 0.1794 0.046 Uiso 1 1 calc R . . C23 C 0.8623(2) 1.4337(3) 0.16061(11) 0.0380(7) Uani 1 1 d . . . H23A H 0.8624 1.3909 0.1952 0.046 Uiso 1 1 calc R . . H23B H 0.8487 1.5196 0.1670 0.046 Uiso 1 1 calc R . . C24 C 0.9839(3) 1.4169(3) 0.14041(13) 0.0436(7) Uani 1 1 d . . . H24A H 0.9851 1.4621 0.1065 0.052 Uiso 1 1 calc R . . H24B H 1.0510 1.4475 0.1674 0.052 Uiso 1 1 calc R . . C25 C 1.1246(3) 1.2657(3) 0.12018(13) 0.0447(7) Uani 1 1 d . . . H25A H 1.1834 1.2754 0.1535 0.054 Uiso 1 1 calc R . . H25B H 1.1484 1.3217 0.0928 0.054 Uiso 1 1 calc R . . C26 C 1.1299(3) 1.1399(3) 0.09998(12) 0.0445(7) Uani 1 1 d . . . H26A H 1.0709 1.1303 0.0667 0.053 Uiso 1 1 calc R . . H26B H 1.2136 1.1228 0.0912 0.053 Uiso 1 1 calc R . . C27 C 1.1232(2) 0.9374(3) 0.12516(12) 0.0395(7) Uani 1 1 d . . . H27A H 1.2098 0.9290 0.1185 0.047 Uiso 1 1 calc R . . H27B H 1.0691 0.9163 0.0916 0.047 Uiso 1 1 calc R . . C28 C 1.0989(2) 0.8548(3) 0.16931(12) 0.0378(7) Uani 1 1 d . . . H28A H 1.1264 0.7731 0.1618 0.045 Uiso 1 1 calc R . . H28B H 1.1445 0.8816 0.2041 0.045 Uiso 1 1 calc R . . C29 C 1.0075(2) 0.5370(3) 0.30833(12) 0.0406(7) Uani 1 1 d . . . C30 C 1.0165(3) 0.3946(3) 0.37915(13) 0.0443(7) Uani 1 1 d . . . H30A H 0.9651 0.3631 0.4051 0.067 Uiso 1 1 calc R . . H30B H 1.0915 0.4298 0.3986 0.067 Uiso 1 1 calc R . . H30C H 1.0389 0.3296 0.3561 0.067 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0364(11) 0.0484(12) 0.0397(12) 0.0057(9) 0.0020(9) 0.0061(9) O2 0.0355(13) 0.100(2) 0.0833(19) 0.0437(16) 0.0105(12) 0.0179(12) O3 0.0253(9) 0.0510(12) 0.0378(11) 0.0086(9) 0.0018(8) 0.0011(8) O4 0.0363(11) 0.0475(12) 0.0366(11) 0.0049(9) -0.0034(8) -0.0059(9) O5 0.0439(12) 0.0581(14) 0.0366(12) -0.0033(10) -0.0027(9) 0.0022(9) O6 0.0570(13) 0.0430(12) 0.0361(11) -0.0064(9) 0.0064(10) -0.0052(9) O7 0.0470(12) 0.0383(12) 0.0328(11) -0.0014(8) -0.0043(9) -0.0101(9) O8 0.0458(12) 0.0396(12) 0.0362(11) 0.0092(9) -0.0057(9) -0.0105(9) O9 0.0370(11) 0.0461(12) 0.0311(11) -0.0083(8) -0.0010(8) -0.0042(8) O10 0.0345(10) 0.0426(12) 0.0455(12) 0.0021(9) 0.0069(9) -0.0047(8) O11 0.0398(11) 0.0426(12) 0.0338(11) -0.0032(9) 0.0157(8) -0.0004(9) O12 0.0268(10) 0.0436(12) 0.0429(12) 0.0058(9) 0.0042(8) 0.0035(8) C1 0.0316(14) 0.0361(15) 0.0283(14) -0.0031(11) 0.0004(11) -0.0006(11) C2 0.0333(14) 0.0349(15) 0.0243(14) -0.0035(11) -0.0035(11) 0.0003(11) C3 0.0252(13) 0.0427(16) 0.0352(16) -0.0037(12) -0.0012(11) 0.0007(11) C4 0.0308(14) 0.0339(15) 0.0308(15) -0.0030(11) 0.0039(11) -0.0018(11) C5 0.0323(14) 0.0347(15) 0.0291(15) 0.0002(11) -0.0019(11) 0.0034(11) C6 0.0276(13) 0.0395(16) 0.0277(14) -0.0057(11) -0.0017(11) -0.0002(11) C7 0.0336(15) 0.0494(18) 0.0317(15) 0.0050(13) 0.0030(12) -0.0027(12) C8 0.0335(15) 0.0567(19) 0.0318(16) 0.0036(13) 0.0031(12) -0.0004(13) C9 0.0391(16) 0.0450(18) 0.052(2) 0.0047(14) -0.0038(14) -0.0077(13) C10 0.0410(16) 0.0487(19) 0.052(2) -0.0059(15) 0.0005(14) 0.0000(14) C11 0.058(2) 0.0492(19) 0.0358(17) -0.0035(14) -0.0004(15) -0.0063(15) C12 0.0524(18) 0.050(2) 0.0382(18) -0.0028(14) -0.0050(14) -0.0119(14) C13 0.0519(19) 0.048(2) 0.0433(18) -0.0166(15) 0.0058(15) -0.0072(14) C14 0.0543(19) 0.0490(19) 0.0312(16) -0.0073(13) -0.0024(14) -0.0144(14) C15 0.0342(14) 0.0407(17) 0.0281(14) -0.0016(12) 0.0083(11) -0.0020(12) C16 0.0320(14) 0.0502(18) 0.0332(16) 0.0008(13) -0.0036(12) -0.0006(12) C17 0.0405(16) 0.0468(18) 0.0307(15) 0.0101(13) -0.0010(12) 0.0040(13) C18 0.0415(16) 0.0384(17) 0.0367(17) 0.0079(12) 0.0004(13) -0.0001(12) C19 0.0322(14) 0.0393(16) 0.0308(15) 0.0021(12) 0.0027(11) -0.0043(12) C20 0.0316(14) 0.0419(17) 0.0253(14) 0.0048(11) 0.0022(11) -0.0016(11) C21 0.0394(15) 0.0419(17) 0.0327(15) 0.0062(12) -0.0027(12) -0.0034(12) C22 0.0417(16) 0.0384(16) 0.0345(16) 0.0012(12) 0.0008(13) 0.0010(12) C23 0.0418(16) 0.0377(16) 0.0321(15) -0.0025(12) -0.0041(12) -0.0044(12) C24 0.0468(17) 0.0371(18) 0.0450(18) 0.0005(13) -0.0011(14) -0.0095(13) C25 0.0355(15) 0.054(2) 0.0447(18) 0.0076(15) 0.0073(13) -0.0080(13) C26 0.0395(16) 0.059(2) 0.0377(17) 0.0036(14) 0.0146(13) -0.0031(14) C27 0.0288(14) 0.0512(18) 0.0399(17) -0.0094(14) 0.0105(12) 0.0019(13) C28 0.0275(14) 0.0422(17) 0.0431(17) -0.0049(13) 0.0026(12) 0.0032(12) C29 0.0294(15) 0.0505(18) 0.0404(17) 0.0028(14) -0.0009(12) 0.0023(12) C30 0.0344(16) 0.0464(18) 0.0516(19) 0.0087(14) 0.0036(13) 0.0051(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C29 1.340(4) . ? O1 C30 1.460(3) . ? O2 C29 1.210(3) . ? O3 C6 1.367(3) . ? O3 C7 1.439(3) . ? O4 C9 1.414(4) . ? O4 C8 1.426(3) . ? O5 C11 1.423(4) . ? O5 C10 1.425(3) . ? O6 C12 1.429(3) . ? O6 C13 1.430(4) . ? O7 C15 1.371(3) . ? O7 C14 1.435(3) . ? O8 C19 1.385(3) . ? O8 C21 1.427(3) . ? O9 C22 1.422(3) . ? O9 C23 1.424(3) . ? O10 C25 1.429(3) . ? O10 C24 1.430(3) . ? O11 C26 1.419(3) . ? O11 C27 1.432(3) . ? O12 C4 1.364(3) . ? O12 C28 1.450(3) . ? C1 C2 1.394(4) . ? C1 C6 1.403(4) . ? C2 C3 1.401(4) . ? C2 C29 1.497(4) . ? C3 C4 1.400(4) . ? C4 C5 1.393(4) . ? C5 C6 1.395(4) . ? C7 C8 1.515(4) . ? C9 C10 1.501(4) . ? C11 C12 1.485(4) . ? C13 C14 1.493(4) . ? C15 C16 1.387(4) . ? C15 C20 1.405(4) . ? C16 C17 1.384(4) . ? C17 C18 1.372(4) . ? C18 C19 1.399(4) . ? C19 C20 1.382(4) . ? C21 C22 1.512(4) . ? C23 C24 1.498(4) . ? C25 C26 1.502(4) . ? C27 C28 1.491(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C29 O1 C30 116.1(2) . . ? C6 O3 C7 119.0(2) . . ? C9 O4 C8 113.7(2) . . ? C11 O5 C10 111.3(2) . . ? C12 O6 C13 113.4(2) . . ? C15 O7 C14 116.9(2) . . ? C19 O8 C21 117.7(2) . . ? C22 O9 C23 112.5(2) . . ? C25 O10 C24 113.3(2) . . ? C26 O11 C27 111.7(2) . . ? C4 O12 C28 118.8(2) . . ? C2 C1 C6 118.0(3) . . ? C1 C2 C3 122.2(2) . . ? C1 C2 C29 121.3(2) . . ? C3 C2 C29 116.5(2) . . ? C4 C3 C2 118.7(2) . . ? O12 C4 C5 114.8(2) . . ? O12 C4 C3 125.2(2) . . ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.4(2) . . ? O3 C6 C5 114.6(2) . . ? O3 C6 C1 124.7(2) . . ? C5 C6 C1 120.7(2) . . ? O3 C7 C8 105.6(2) . . ? O4 C8 C7 113.0(2) . . ? O4 C9 C10 108.8(2) . . ? O5 C10 C9 109.2(3) . . ? O5 C11 C12 109.5(3) . . ? O6 C12 C11 114.3(3) . . ? O6 C13 C14 109.7(2) . . ? O7 C14 C13 109.2(2) . . ? O7 C15 C16 124.9(2) . . ? O7 C15 C20 114.6(2) . . ? C16 C15 C20 120.5(3) . . ? C17 C16 C15 118.5(3) . . ? C18 C17 C16 122.6(3) . . ? C17 C18 C19 118.3(3) . . ? C20 C19 O8 123.5(2) . . ? C20 C19 C18 120.9(2) . . ? O8 C19 C18 115.6(2) . . ? C19 C20 C15 119.2(2) . . ? O8 C21 C22 108.7(2) . . ? O9 C22 C21 109.2(2) . . ? O9 C23 C24 109.9(2) . . ? O10 C24 C23 109.4(2) . . ? O10 C25 C26 110.0(2) . . ? O11 C26 C25 110.4(2) . . ? O11 C27 C28 110.1(2) . . ? O12 C28 C27 107.8(2) . . ? O2 C29 O1 122.9(3) . . ? O2 C29 C2 124.0(3) . . ? O1 C29 C2 113.1(2) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.264 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.049 #===END data_1b _database_code_depnum_ccdc_archive 'CCDC 262642' #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 10.3115(19) _cell_angle_alpha 76.203(12) _cell_length_b 11.0844(17) _cell_angle_beta 70.914(14) _cell_length_c 13.8563(19) _cell_angle_gamma 83.447(14) _cell_volume 1452.4(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C29 H39 O11 ' _chemical_formula_moiety ' C29 H39 O11 ' _chemical_compound_source ; ? ; _chemical_formula_weight 563.62 _cell_measurement_reflns_used 9130 _cell_measurement_theta_min 2.828 _cell_measurement_theta_max 29.386 _cell_measurement_temperature 100(2) _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.21 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.58 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 602 _exptl_absorpt_coefficient_mu 0.099 # Sheldrick geometric definitions 1.00 1.00 _diffrn_measurement_device_type 'Oxford Diffraction Sapphire2 CCD' _diffrn_radiation_monochromator graphite _computing_data_collection 'Crysalis (Oxford Diffraction)' _computing_data_reduction 'Crysalis (Oxford Diffraction)' _computing_cell_refinement 'Crysalis (Oxford Diffraction)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _diffrn_measurement_method 'phi and omega scans' _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 100(2) _diffrn_reflns_number 18237 _reflns_number_total 9130 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 9130 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 10152 _diffrn_reflns_theta_min 3.405 _diffrn_reflns_theta_max 32.077 _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 29.190 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -14 _reflns_limit_h_max 15 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _refine_diff_density_min -0.27 _refine_diff_density_max 0.49 _refine_ls_number_reflns 4621 _refine_ls_number_parameters 371 #_refine_ls_R_factor_ref 0.0474 _refine_ls_wR_factor_ref 0.0704 _refine_ls_goodness_of_fit_ref 0.8278 #_reflns_number_all 9130 _refine_ls_R_factor_all 0.0799 _refine_ls_wR_factor_all 0.0920 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 4621 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_gt 0.0704 _refine_ls_shift/su_max 0.000447 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 774. 855. 570. ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Walker, N., and Stuart, D. Acta Cryst, (1983) A39, 158-166 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 1.7305(2) -0.1378(2) -0.15079(17) 0.0228 1.0000 Uani . C2 C 1.6193(2) -0.2036(2) -0.07828(17) 0.0217 1.0000 Uani . C3 C 1.6456(2) -0.3145(2) -0.01383(17) 0.0232 1.0000 Uani . C4 C 1.7787(2) -0.3591(2) -0.02082(19) 0.0272 1.0000 Uani . C5 C 1.8886(2) -0.2937(2) -0.0950(2) 0.0279 1.0000 Uani . C6 C 1.8646(2) -0.1832(2) -0.16025(19) 0.0270 1.0000 Uani . C7 C 2.0325(3) -0.3446(3) -0.1035(2) 0.0396 1.0000 Uani . O8 O 2.0610(2) -0.36597(19) -0.00284(18) 0.0324 0.8000 Uani . O9 O 1.54549(16) -0.38819(15) 0.05916(12) 0.0266 1.0000 Uani . C10 C 1.4067(2) -0.3535(2) 0.06320(18) 0.0259 1.0000 Uani . C11 C 1.3153(2) -0.4459(2) 0.14880(18) 0.0255 1.0000 Uani . O12 O 1.30577(16) -0.41943(14) 0.24647(12) 0.0257 1.0000 Uani . C13 C 1.2222(2) -0.5063(2) 0.33039(18) 0.0277 1.0000 Uani . C14 C 1.2053(2) -0.4688(2) 0.43122(18) 0.0303 1.0000 Uani . O15 O 1.12243(17) -0.35775(15) 0.43569(12) 0.0291 1.0000 Uani . C16 C 1.1130(3) -0.3100(2) 0.52433(18) 0.0315 1.0000 Uani . C17 C 1.0190(3) -0.1967(2) 0.5260(2) 0.0327 1.0000 Uani . O18 O 0.88206(17) -0.23385(15) 0.55059(13) 0.0305 1.0000 Uani . C19 C 0.7811(3) -0.1354(2) 0.56474(19) 0.0315 1.0000 Uani . C20 C 0.7575(3) -0.0739(2) 0.46240(18) 0.0311 1.0000 Uani . O21 O 0.66870(19) 0.03257(17) 0.48194(13) 0.0352 1.0000 Uani . C22 C 0.6463(2) 0.1155(2) 0.39793(18) 0.0277 1.0000 Uani . C23 C 0.6898(2) 0.0908(2) 0.29761(18) 0.0248 1.0000 Uani . C24 C 0.6670(2) 0.1819(2) 0.21676(17) 0.0230 1.0000 Uani . C25 C 0.6024(2) 0.2956(2) 0.23372(19) 0.0266 1.0000 Uani . C26 C 0.5581(2) 0.3167(2) 0.33514(19) 0.0297 1.0000 Uani . C27 C 0.5784(2) 0.2271(2) 0.41719(19) 0.0296 1.0000 Uani . O28 O 0.70647(16) 0.16566(15) 0.11521(12) 0.0242 1.0000 Uani . C29 C 0.7900(2) 0.0569(2) 0.09245(17) 0.0235 1.0000 Uani . C30 C 0.8242(2) 0.0610(2) -0.02213(17) 0.0236 1.0000 Uani . O31 O 0.91418(16) 0.16007(16) -0.07994(12) 0.0269 1.0000 Uani . C32 C 0.9451(2) 0.1742(2) -0.19023(17) 0.0263 1.0000 Uani . C33 C 1.0492(2) 0.2728(2) -0.24537(19) 0.0288 1.0000 Uani . O34 O 1.17741(15) 0.22680(15) -0.23095(12) 0.0259 1.0000 Uani . C35 C 1.2736(2) 0.3227(2) -0.2652(2) 0.0290 1.0000 Uani . C36 C 1.4034(2) 0.2713(2) -0.24169(18) 0.0263 1.0000 Uani . O37 O 1.47219(16) 0.19017(15) -0.30978(12) 0.0254 1.0000 Uani . C38 C 1.6014(2) 0.1419(2) -0.29730(17) 0.0240 1.0000 Uani . C39 C 1.5829(2) 0.0238(2) -0.21323(18) 0.0242 1.0000 Uani . O40 O 1.71805(16) -0.02497(15) -0.21555(12) 0.0265 1.0000 Uani . H21 H 1.5230(2) -0.1717(2) -0.07272(17) 0.0252 1.0000 Uiso . H41 H 1.7958(2) -0.4383(2) 0.02667(19) 0.0346 1.0000 Uiso . H61 H 1.9434(2) -0.1369(2) -0.21442(19) 0.0335 1.0000 Uiso . H101 H 1.3836(2) -0.2682(2) 0.07763(18) 0.0300 1.0000 Uiso . H102 H 1.3943(2) -0.3546(2) -0.00521(18) 0.0300 1.0000 Uiso . H111 H 1.3542(2) -0.5323(2) 0.14592(18) 0.0313 1.0000 Uiso . H112 H 1.2217(2) -0.4381(2) 0.14057(18) 0.0313 1.0000 Uiso . H131 H 1.2672(2) -0.5912(2) 0.33158(18) 0.0308 1.0000 Uiso . H132 H 1.1301(2) -0.5066(2) 0.32105(18) 0.0308 1.0000 Uiso . H141 H 1.2976(2) -0.4540(2) 0.43444(18) 0.0322 1.0000 Uiso . H142 H 1.1608(2) -0.5362(2) 0.49170(18) 0.0322 1.0000 Uiso . H161 H 1.2064(3) -0.2885(2) 0.52063(18) 0.0377 1.0000 Uiso . H162 H 1.0747(3) -0.3740(2) 0.58949(18) 0.0377 1.0000 Uiso . H171 H 1.0249(3) -0.1529(2) 0.5796(2) 0.0398 1.0000 Uiso . H172 H 1.0462(3) -0.1396(2) 0.4555(2) 0.0398 1.0000 Uiso . H191 H 0.8139(3) -0.0725(2) 0.59167(19) 0.0359 1.0000 Uiso . H192 H 0.6928(3) -0.1687(2) 0.61612(19) 0.0359 1.0000 Uiso . H201 H 0.8465(3) -0.0473(2) 0.40806(18) 0.0359 1.0000 Uiso . H202 H 0.7138(3) -0.1324(2) 0.43850(18) 0.0359 1.0000 Uiso . H231 H 0.7360(2) 0.0091(2) 0.28494(18) 0.0307 1.0000 Uiso . H251 H 0.5879(2) 0.3611(2) 0.17418(19) 0.0315 1.0000 Uiso . H261 H 0.5115(2) 0.3982(2) 0.34812(19) 0.0364 1.0000 Uiso . H271 H 0.5442(2) 0.2417(2) 0.48999(19) 0.0360 1.0000 Uiso . H291 H 0.8769(2) 0.0560(2) 0.10981(17) 0.0280 1.0000 Uiso . H292 H 0.7387(2) -0.0194(2) 0.13438(17) 0.0280 1.0000 Uiso . H301 H 0.8695(2) -0.0197(2) -0.03830(17) 0.0286 1.0000 Uiso . H302 H 0.7376(2) 0.0761(2) -0.04162(17) 0.0286 1.0000 Uiso . H321 H 0.9843(2) 0.0936(2) -0.21018(17) 0.0308 1.0000 Uiso . H322 H 0.8593(2) 0.1984(2) -0.21014(17) 0.0308 1.0000 Uiso . H331 H 1.0593(2) 0.2939(2) -0.32170(19) 0.0331 1.0000 Uiso . H332 H 1.0177(2) 0.3488(2) -0.21568(19) 0.0331 1.0000 Uiso . H351 H 1.2951(2) 0.3544(2) -0.3424(2) 0.0331 1.0000 Uiso . H352 H 1.2339(2) 0.3925(2) -0.2287(2) 0.0331 1.0000 Uiso . H361 H 1.4644(2) 0.3404(2) -0.25211(18) 0.0321 1.0000 Uiso . H362 H 1.3795(2) 0.2242(2) -0.16743(18) 0.0321 1.0000 Uiso . H381 H 1.6436(2) 0.2049(2) -0.27697(17) 0.0291 1.0000 Uiso . H382 H 1.6633(2) 0.1235(2) -0.36504(17) 0.0291 1.0000 Uiso . H391 H 1.5315(2) 0.0424(2) -0.14316(18) 0.0282 1.0000 Uiso . H392 H 1.5316(2) -0.0369(2) -0.22852(18) 0.0282 1.0000 Uiso . O41 O 2.052(1) -0.4449(9) -0.161(1) 0.0617 0.2000 Uani . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0244(11) 0.0252(11) 0.0226(11) -0.0096(9) -0.0093(9) -0.0011(9) C2 0.021(1) 0.0262(11) 0.021(1) -0.0092(9) -0.0075(8) 0.0012(9) C3 0.0237(11) 0.0255(11) 0.0232(11) -0.0103(9) -0.0075(9) -0.0007(9) C4 0.0273(12) 0.0227(11) 0.0371(13) -0.012(1) -0.015(1) 0.0027(9) C5 0.0231(11) 0.0252(12) 0.0421(14) -0.0170(11) -0.013(1) 0.0021(9) C6 0.0221(11) 0.0292(13) 0.0334(13) -0.014(1) -0.007(1) -0.0034(9) C7 0.0237(13) 0.0374(15) 0.0632(19) -0.0202(14) -0.0153(13) 0.0026(11) O8 0.0314(12) 0.0257(11) 0.0464(13) -0.005(1) -0.023(1) 0.0016(9) O9 0.0240(8) 0.0261(9) 0.0279(9) -0.0042(7) -0.0079(7) 0.0022(7) C10 0.0240(11) 0.0291(12) 0.0236(11) -0.0056(9) -0.0078(9) 0.0041(9) C11 0.0263(12) 0.0219(11) 0.0304(12) -0.0057(9) -0.012(1) -0.0005(9) O12 0.0300(9) 0.0234(8) 0.0224(8) -0.0023(6) -0.0050(7) -0.0104(7) C13 0.0257(12) 0.0211(11) 0.0325(13) 0.001(1) -0.007(1) -0.0055(9) C14 0.0263(12) 0.0317(13) 0.0268(12) 0.005(1) -0.007(1) -0.004(1) O15 0.0301(9) 0.0305(9) 0.0252(9) -0.0021(7) -0.0089(7) -0.0027(7) C16 0.0276(13) 0.0419(15) 0.0242(12) -0.0026(11) -0.007(1) -0.0116(11) C17 0.0350(14) 0.0323(14) 0.0310(13) -0.0053(11) -0.0073(11) -0.0138(11) O18 0.0296(9) 0.0253(9) 0.0344(9) -0.0033(7) -0.0080(7) -0.0050(7) C19 0.0374(14) 0.0276(13) 0.0251(12) -0.002(1) -0.0061(11) -0.002(1) C20 0.0412(14) 0.0268(13) 0.0236(12) -0.006(1) -0.0084(11) 0.0015(11) O21 0.0435(11) 0.038(1) 0.0225(9) -0.0082(8) -0.0106(8) 0.0086(8) C22 0.0265(12) 0.0339(13) 0.0243(11) -0.006(1) -0.0106(9) 0.000(1) C23 0.0231(11) 0.0288(12) 0.0249(11) -0.0099(9) -0.0079(9) -0.0004(9) C24 0.017(1) 0.0323(12) 0.0223(11) -0.0105(9) -0.0053(8) -0.0045(9) C25 0.0239(11) 0.0299(13) 0.0286(12) -0.010(1) -0.010(1) 0.0012(9) C26 0.0244(12) 0.0360(14) 0.0327(13) -0.0146(11) -0.011(1) 0.005(1) C27 0.0253(12) 0.0396(14) 0.0273(12) -0.0169(11) -0.007(1) 0.003(1) O28 0.0250(8) 0.0286(9) 0.0203(8) -0.0100(7) -0.0062(6) 0.0019(7) C29 0.0224(11) 0.0259(12) 0.0236(11) -0.0096(9) -0.0072(9) 0.0025(9) C30 0.0217(11) 0.0273(12) 0.0235(11) -0.0100(9) -0.0062(9) -0.0005(9) O31 0.0241(8) 0.0359(9) 0.0207(8) -0.0087(7) -0.0035(6) -0.0058(7) C32 0.0196(11) 0.0368(13) 0.0233(11) -0.009(1) -0.0069(9) 0.0017(9) C33 0.0232(11) 0.0341(13) 0.0263(12) -0.003(1) -0.0077(9) 0.001(1) O34 0.0188(8) 0.0277(9) 0.0293(9) -0.0031(7) -0.0070(7) -0.0012(6) C35 0.0255(12) 0.0266(12) 0.0324(13) -0.004(1) -0.007(1) -0.002(1) C36 0.0255(12) 0.0262(12) 0.0277(12) -0.010(1) -0.0056(9) -0.0031(9) O37 0.0231(8) 0.0333(9) 0.0219(8) -0.0089(7) -0.0081(7) 0.0004(7) C38 0.019(1) 0.0299(12) 0.0216(11) -0.0045(9) -0.0046(9) -0.0031(9) C39 0.019(1) 0.0297(12) 0.0236(11) -0.0040(9) -0.0064(9) -0.0026(9) O40 0.0204(8) 0.0310(9) 0.0266(8) -0.0026(7) -0.0070(7) -0.0036(7) O41 0.031(5) 0.030(5) 0.11(1) 0.005(6) -0.018(6) 0.004(4) _refine_ls_extinction_coef 10.5(12) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.395(3) yes C1 . C6 . 1.391(3) yes C1 . O40 . 1.374(3) yes C2 . C3 . 1.393(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.385(3) yes C3 . O9 . 1.368(3) yes C4 . C5 . 1.392(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.388(3) yes C5 . C7 . 1.504(3) yes C6 . H61 . 1.000 no C7 . O8 . 1.478(4) yes C7 . O41 . 1.478(12) yes O9 . C10 . 1.425(3) yes C10 . C11 . 1.501(3) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . O12 . 1.422(3) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no O12 . C13 . 1.422(3) yes C13 . C14 . 1.502(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C14 . O15 . 1.418(3) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no O15 . C16 . 1.421(3) yes C16 . C17 . 1.496(4) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . O18 . 1.425(3) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no O18 . C19 . 1.422(3) yes C19 . C20 . 1.504(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . O21 . 1.431(3) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no O21 . C22 . 1.368(3) yes C22 . C23 . 1.398(3) yes C22 . C27 . 1.389(3) yes C23 . C24 . 1.381(3) yes C23 . H231 . 1.000 no C24 . C25 . 1.391(3) yes C24 . O28 . 1.381(3) yes C25 . C26 . 1.397(3) yes C25 . H251 . 1.000 no C26 . C27 . 1.376(3) yes C26 . H261 . 1.000 no C27 . H271 . 1.000 no O28 . C29 . 1.436(3) yes C29 . C30 . 1.500(3) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . O31 . 1.427(3) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no O31 . C32 . 1.428(3) yes C32 . C33 . 1.504(3) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C33 . O34 . 1.420(3) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no O34 . C35 . 1.425(3) yes C35 . C36 . 1.498(3) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no C36 . O37 . 1.423(3) yes C36 . H361 . 1.000 no C36 . H362 . 1.000 no O37 . C38 . 1.427(3) yes C38 . C39 . 1.513(3) yes C38 . H381 . 1.000 no C38 . H382 . 1.000 no C39 . O40 . 1.429(3) yes C39 . H391 . 1.000 no C39 . H392 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 120.8(2) yes C2 . C1 . O40 . 123.9(2) yes C6 . C1 . O40 . 115.3(2) yes C1 . C2 . C3 . 118.4(2) yes C1 . C2 . H21 . 120.66(13) no C3 . C2 . H21 . 120.89(13) no C2 . C3 . C4 . 121.3(2) yes C2 . C3 . O9 . 124.0(2) yes C4 . C3 . O9 . 114.8(2) yes C3 . C4 . C5 . 119.6(2) yes C3 . C4 . H41 . 120.27(14) no C5 . C4 . H41 . 120.14(14) no C4 . C5 . C6 . 120.0(2) yes C4 . C5 . C7 . 119.1(2) yes C6 . C5 . C7 . 120.9(2) yes C1 . C6 . C5 . 119.8(2) yes C1 . C6 . H61 . 120.05(14) no C5 . C6 . H61 . 120.11(14) no C5 . C7 . O8 . 111.9(2) yes C5 . C7 . O41 . 104.6(4) yes O8 . C7 . O41 . 121.7(5) yes C3 . O9 . C10 . 117.42(17) yes O9 . C10 . C11 . 108.28(19) yes O9 . C10 . H101 . 109.84(12) no C11 . C10 . H101 . 110.10(13) no O9 . C10 . H102 . 109.49(11) no C11 . C10 . H102 . 109.64(12) no H101 . C10 . H102 . 109.467 no C10 . C11 . O12 . 108.42(18) yes C10 . C11 . H111 . 110.15(13) no O12 . C11 . H111 . 109.84(11) no C10 . C11 . H112 . 109.57(12) no O12 . C11 . H112 . 109.36(12) no H111 . C11 . H112 . 109.467 no C11 . O12 . C13 . 110.54(17) yes O12 . C13 . C14 . 108.77(18) yes O12 . C13 . H131 . 109.51(12) no C14 . C13 . H131 . 109.83(13) no O12 . C13 . H132 . 109.72(12) no C14 . C13 . H132 . 109.53(13) no H131 . C13 . H132 . 109.467 no C13 . C14 . O15 . 109.29(19) yes C13 . C14 . H141 . 109.37(13) no O15 . C14 . H141 . 109.27(12) no C13 . C14 . H142 . 109.84(12) no O15 . C14 . H142 . 109.59(12) no H141 . C14 . H142 . 109.467 no C14 . O15 . C16 . 112.43(18) yes O15 . C16 . C17 . 109.1(2) yes O15 . C16 . H161 . 109.59(12) no C17 . C16 . H161 . 110.13(13) no O15 . C16 . H162 . 109.51(12) no C17 . C16 . H162 . 109.02(13) no H161 . C16 . H162 . 109.467 no C16 . C17 . O18 . 108.74(19) yes C16 . C17 . H171 . 110.03(13) no O18 . C17 . H171 . 109.84(13) no C16 . C17 . H172 . 109.23(14) no O18 . C17 . H172 . 109.52(12) no H171 . C17 . H172 . 109.467 no C17 . O18 . C19 . 113.97(18) yes O18 . C19 . C20 . 110.20(19) yes O18 . C19 . H191 . 109.15(12) no C20 . C19 . H191 . 109.05(14) no O18 . C19 . H192 . 109.79(12) no C20 . C19 . H192 . 109.16(14) no H191 . C19 . H192 . 109.467 no C19 . C20 . O21 . 105.84(19) yes C19 . C20 . H201 . 110.22(14) no O21 . C20 . H201 . 110.05(13) no C19 . C20 . H202 . 110.28(14) no O21 . C20 . H202 . 110.94(13) no H201 . C20 . H202 . 109.467 no C20 . O21 . C22 . 117.83(18) yes O21 . C22 . C23 . 122.3(2) yes O21 . C22 . C27 . 116.4(2) yes C23 . C22 . C27 . 121.3(2) yes C22 . C23 . C24 . 118.3(2) yes C22 . C23 . H231 . 120.70(14) no C24 . C23 . H231 . 121.00(13) no C23 . C24 . C25 . 121.4(2) yes C23 . C24 . O28 . 122.3(2) yes C25 . C24 . O28 . 116.3(2) yes C24 . C25 . C26 . 119.0(2) yes C24 . C25 . H251 . 120.42(14) no C26 . C25 . H251 . 120.62(15) no C25 . C26 . C27 . 120.8(2) yes C25 . C26 . H261 . 119.55(15) no C27 . C26 . H261 . 119.67(14) no C22 . C27 . C26 . 119.2(2) yes C22 . C27 . H271 . 120.24(14) no C26 . C27 . H271 . 120.53(14) no C24 . O28 . C29 . 117.56(17) yes O28 . C29 . C30 . 108.27(18) yes O28 . C29 . H291 . 109.99(11) no C30 . C29 . H291 . 109.19(12) no O28 . C29 . H292 . 109.77(11) no C30 . C29 . H292 . 110.13(12) no H291 . C29 . H292 . 109.467 no C29 . C30 . O31 . 109.09(18) yes C29 . C30 . H301 . 110.04(12) no O31 . C30 . H301 . 109.78(11) no C29 . C30 . H302 . 109.05(12) no O31 . C30 . H302 . 109.39(11) no H301 . C30 . H302 . 109.467 no C30 . O31 . C32 . 112.25(17) yes O31 . C32 . C33 . 108.94(19) yes O31 . C32 . H321 . 109.23(12) no C33 . C32 . H321 . 109.28(13) no O31 . C32 . H322 . 109.67(11) no C33 . C32 . H322 . 110.24(13) no H321 . C32 . H322 . 109.467 no C32 . C33 . O34 . 109.03(19) yes C32 . C33 . H331 . 109.47(13) no O34 . C33 . H331 . 109.55(12) no C32 . C33 . H332 . 109.36(13) no O34 . C33 . H332 . 109.94(12) no H331 . C33 . H332 . 109.467 no C33 . O34 . C35 . 111.56(18) yes O34 . C35 . C36 . 109.39(19) yes O34 . C35 . H351 . 109.50(12) no C36 . C35 . H351 . 108.85(13) no O34 . C35 . H352 . 109.78(12) no C36 . C35 . H352 . 109.84(13) no H351 . C35 . H352 . 109.467 no C35 . C36 . O37 . 108.95(19) yes C35 . C36 . H361 . 110.23(13) no O37 . C36 . H361 . 109.59(11) no C35 . C36 . H362 . 108.85(13) no O37 . C36 . H362 . 109.74(12) no H361 . C36 . H362 . 109.467 no C36 . O37 . C38 . 113.09(17) yes O37 . C38 . C39 . 110.43(17) yes O37 . C38 . H381 . 109.45(12) no C39 . C38 . H381 . 109.09(12) no O37 . C38 . H382 . 109.05(11) no C39 . C38 . H382 . 109.34(12) no H381 . C38 . H382 . 109.467 no C38 . C39 . O40 . 106.11(17) yes C38 . C39 . H391 . 110.46(12) no O40 . C39 . H391 . 110.25(11) no C38 . C39 . H392 . 110.10(12) no O40 . C39 . H392 . 110.41(12) no H391 . C39 . H392 . 109.467 no C1 . O40 . C39 . 117.98(17) yes #===END data_1b2 _database_code_depnum_ccdc_archive 'CCDC 262643' _audit_creation_date 03-06-05 _audit_creation_method CRYSTALS_ver_12-03-99 #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.6764(12) _cell_angle_alpha 62.902(11) _cell_length_b 15.9293(19) _cell_angle_beta 83.880(9) _cell_length_c 16.8706(18) _cell_angle_gamma 73.69(1) _cell_volume 2680.1(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'P ' 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C47 H67 F12 N2 O13 P2 ' _chemical_formula_moiety ' C47 H67 F12 N2 O13 P2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 1157.98 _cell_measurement_reflns_used 10960 _cell_measurement_theta_min 2.828 _cell_measurement_theta_max 29.386 _cell_measurement_temperature 100(2) _exptl_crystal_description ' prism ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1210 _exptl_absorpt_coefficient_mu 0.185 # Sheldrick geometric definitions 1.00 1.00 _diffrn_measurement_device_type 'Oxford Diffraction Sapphire2 CCD' _diffrn_radiation_monochromator graphite _computing_data_collection 'Crysalis (Oxford Diffraction)' _computing_data_reduction 'Crysalis (Oxford Diffraction)' _computing_cell_refinement 'Crysalis (Oxford Diffraction)' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _diffrn_measurement_method 'phi and omega scans' _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 100(2) _diffrn_reflns_number 25101 _reflns_number_total 10960 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 10960 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 12749 _diffrn_reflns_theta_min 2.773 _diffrn_reflns_theta_max 27.971 _diffrn_measured_fraction_theta_max 0.848 _diffrn_reflns_theta_full 25.454 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -14 _reflns_limit_h_max 15 _reflns_limit_k_min -17 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.50 _refine_diff_density_max 0.63 _refine_ls_number_reflns 7739 _refine_ls_number_parameters 685 #_refine_ls_R_factor_ref 0.1570 _refine_ls_wR_factor_ref 0.1808 _refine_ls_goodness_of_fit_ref 0.8671 #_reflns_number_all 10960 _refine_ls_R_factor_all 0.1991 _refine_ls_wR_factor_all 0.1882 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>0.50u(I) _reflns_number_gt 7739 _refine_ls_R_factor_gt 0.1570 _refine_ls_wR_factor_gt 0.1808 _refine_ls_shift/su_max 0.000441 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 405. 529. 350. 144. 26.2 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_attached_hydrogens P1 P -0.30684(17) 0.07573(14) 1.20763(12) 0.0311 1.0000 Uani . F2 F -0.2150(4) 0.0691(3) 1.1304(3) 0.0511 1.0000 Uani . F3 F -0.3965(4) 0.0854(4) 1.2821(3) 0.0572 1.0000 Uani . F4 F -0.2344(4) 0.1382(4) 1.2220(3) 0.0627 1.0000 Uani . F5 F -0.2209(5) -0.0184(4) 1.2780(3) 0.0886 1.0000 Uani . F6 F -0.3760(6) 0.0164(5) 1.1891(4) 0.0973 1.0000 Uani . F7 F -0.3868(5) 0.1739(4) 1.1346(4) 0.0853 1.0000 Uani . P8 P 0.01838(16) 0.29341(15) 1.10037(12) 0.0312 1.0000 Uani . F9 F 0.1557(4) 0.2516(3) 1.1292(3) 0.0483 1.0000 Uani . F10 F -0.0074(4) 0.3490(3) 1.1598(3) 0.0507 1.0000 Uani . F11 F -0.1171(4) 0.3346(5) 1.0705(5) 0.1008 1.0000 Uani . F12 F 0.0437(5) 0.2345(6) 1.0434(5) 0.1197 1.0000 Uani . F13 F 0.0497(6) 0.3834(5) 1.0209(4) 0.1181 1.0000 Uani . F14 F -0.0060(6) 0.2007(4) 1.1824(5) 0.1161 1.0000 Uani . C15 C -0.2093(5) 0.2364(5) 0.8229(4) 0.0217 1.0000 Uani . C16 C -0.1596(5) 0.1793(4) 0.7726(4) 0.0207 1.0000 Uani . C17 C -0.0860(6) 0.0843(5) 0.8153(5) 0.0278 1.0000 Uani . C18 C -0.0423(6) 0.0311(5) 0.7683(4) 0.0308 1.0000 Uani . N19 N -0.0682(5) 0.0706(4) 0.6808(3) 0.0286 1.0000 Uani . C20 C -0.1421(6) 0.1591(5) 0.6388(4) 0.0363 1.0000 Uani . C21 C -0.1894(6) 0.2145(5) 0.6831(4) 0.0340 1.0000 Uani . C22 C -0.0142(6) 0.0121(5) 0.6311(5) 0.0359 1.0000 Uani . C23 C -0.3126(6) 0.3113(5) 0.7958(4) 0.0317 1.0000 Uani . C24 C -0.3611(6) 0.3597(5) 0.8469(5) 0.0320 1.0000 Uani . N25 N -0.3076(5) 0.3342(4) 0.9236(4) 0.0279 1.0000 Uani . C26 C -0.2055(6) 0.2628(5) 0.9512(5) 0.0308 1.0000 Uani . C27 C -0.1549(6) 0.2137(5) 0.9020(4) 0.0274 1.0000 Uani . C28 C -0.3628(6) 0.3845(5) 0.9796(5) 0.0347 1.0000 Uani . C29 C -0.4674(6) 0.1303(5) 0.8945(4) 0.0268 1.0000 Uani . C30 C -0.4642(6) 0.1191(5) 0.8172(4) 0.0263 1.0000 Uani . C31 C -0.3826(6) 0.0410(5) 0.8105(4) 0.0242 1.0000 Uani . C32 C -0.3017(6) -0.0253(5) 0.8800(4) 0.0275 1.0000 Uani . C33 C -0.3045(6) -0.0110(5) 0.9569(4) 0.0270 1.0000 Uani . C34 C -0.3859(6) 0.0659(5) 0.9636(4) 0.0254 1.0000 Uani . C35 C -0.2155(6) -0.0816(5) 1.0326(4) 0.0347 1.0000 Uani . O36 O -0.1196(4) -0.0434(4) 1.0338(3) 0.0378 1.0000 Uani . O37 O -0.3852(4) 0.0358(3) 0.7324(3) 0.0312 1.0000 Uani . C38 C -0.3228(6) -0.0547(5) 0.7308(4) 0.0339 1.0000 Uani . C39 C -0.3425(7) -0.0439(6) 0.6387(5) 0.0389 1.0000 Uani . O40 O -0.2871(4) 0.0288(4) 0.5770(3) 0.0375 1.0000 Uani . C41 C -0.2975(7) 0.0445(6) 0.4880(5) 0.0409 1.0000 Uani . C42 C -0.2740(7) 0.1394(6) 0.4260(5) 0.0418 1.0000 Uani . O43 O -0.1538(4) 0.1377(3) 0.4368(3) 0.0318 1.0000 Uani . C44 C -0.1291(7) 0.2258(6) 0.3712(5) 0.0418 1.0000 Uani . C45 C -0.0054(7) 0.2292(6) 0.3825(5) 0.0389 1.0000 Uani . O46 O 0.0068(5) 0.2310(4) 0.4646(3) 0.0415 1.0000 Uani . C47 C 0.1127(8) 0.2578(7) 0.4656(6) 0.0565 1.0000 Uani . C48 C 0.1336(7) 0.2454(6) 0.5580(6) 0.0505 1.0000 Uani . O49 O 0.0402(4) 0.3180(4) 0.5730(3) 0.0416 1.0000 Uani . C50 C 0.0533(7) 0.3299(5) 0.6472(5) 0.0339 1.0000 Uani . C51 C -0.0371(6) 0.3997(5) 0.6600(5) 0.0329 1.0000 Uani . C52 C -0.0313(6) 0.4182(5) 0.7322(4) 0.0302 1.0000 Uani . C53 C 0.0670(6) 0.3672(5) 0.7906(4) 0.0357 1.0000 Uani . C54 C 0.1574(7) 0.2998(5) 0.7756(5) 0.0406 1.0000 Uani . C55 C 0.1512(7) 0.2780(6) 0.7056(5) 0.0404 1.0000 Uani . O56 O -0.1237(4) 0.4890(4) 0.7384(3) 0.0363 1.0000 Uani . C57 C -0.1197(6) 0.5079(6) 0.8133(5) 0.0433 1.0000 Uani . C58 C -0.2201(6) 0.5978(6) 0.8011(6) 0.0436 1.0000 Uani . O59 O -0.3326(4) 0.5784(3) 0.8005(3) 0.0341 1.0000 Uani . C60 C -0.4275(7) 0.6580(5) 0.7987(6) 0.0439 1.0000 Uani . C61 C -0.5429(7) 0.6515(5) 0.7747(5) 0.0379 1.0000 Uani . O62 O -0.5734(4) 0.5679(3) 0.8420(3) 0.0323 1.0000 Uani . C63 C -0.6880(6) 0.5638(5) 0.8229(5) 0.0337 1.0000 Uani . C64 C -0.7187(6) 0.4780(5) 0.8955(5) 0.0384 1.0000 Uani . O65 O -0.6344(4) 0.3915(3) 0.8999(3) 0.0323 1.0000 Uani . C66 C -0.6623(6) 0.3061(5) 0.9649(5) 0.0341 1.0000 Uani . C67 C -0.5624(6) 0.2191(5) 0.9765(4) 0.0301 1.0000 Uani . O68 O -0.5541(4) 0.2083(3) 0.8957(3) 0.0325 1.0000 Uani . C69 C -0.5810(16) 0.2830(13) 0.473(1) 0.1521 1.0000 Uani . O70 O -0.5943(8) 0.2269(7) 0.4331(6) 0.1182 1.0000 Uani . C71 C -0.647(1) 0.3921(8) 0.4276(7) 0.0844 1.0000 Uani . C72 C -0.5305(11) 0.2298(11) 0.5653(7) 0.1436 1.0000 Uani . C73 C -0.6820(9) 0.5348(8) 0.5707(7) 0.0754 1.0000 Uani . C74 C -0.8096(8) 0.5381(7) 0.5849(7) 0.0744 1.0000 Uani . C75 C -0.5963(9) 0.4486(9) 0.6372(8) 0.1031 1.0000 Uani . O76 O -0.6525(8) 0.6021(8) 0.5064(7) 0.1707 1.0000 Uani . H171 H -0.0640(6) 0.0559(5) 0.8797(5) 0.0351 1.0000 Uiso . H181 H 0.0077(6) -0.0377(5) 0.7994(4) 0.0397 1.0000 Uiso . H201 H -0.1640(6) 0.1849(5) 0.5747(4) 0.0408 1.0000 Uiso . H211 H -0.2436(6) 0.2815(5) 0.6509(4) 0.0382 1.0000 Uiso . H221 H -0.0409(6) 0.0507(5) 0.5671(5) 0.0464 1.0000 Uiso . H222 H 0.0747(6) -0.0038(5) 0.6355(5) 0.0464 1.0000 Uiso . H223 H -0.0400(6) -0.0498(5) 0.6578(5) 0.0464 1.0000 Uiso . H231 H -0.3526(6) 0.3309(5) 0.7381(4) 0.0424 1.0000 Uiso . H241 H -0.4361(6) 0.4140(5) 0.8267(5) 0.0385 1.0000 Uiso . H261 H -0.1667(6) 0.2449(5) 1.0088(5) 0.0374 1.0000 Uiso . H271 H -0.0776(6) 0.1620(5) 0.9220(4) 0.0306 1.0000 Uiso . H281 H -0.3123(6) 0.3570(5) 1.0346(5) 0.0506 1.0000 Uiso . H282 H -0.4444(6) 0.3748(5) 0.9968(5) 0.0506 1.0000 Uiso . H283 H -0.3687(6) 0.4560(5) 0.9447(5) 0.0506 1.0000 Uiso . H301 H -0.5213(6) 0.1677(5) 0.7667(4) 0.0347 1.0000 Uiso . H321 H -0.2430(6) -0.0824(5) 0.8759(4) 0.0324 1.0000 Uiso . H341 H -0.3860(6) 0.0757(5) 1.0181(4) 0.0290 1.0000 Uiso . H351 H -0.2585(6) -0.0953(5) 1.0900(4) 0.0451 1.0000 Uiso . H352 H -0.1828(6) -0.1438(5) 1.0271(4) 0.0451 1.0000 Uiso . H381 H -0.3526(6) -0.1095(5) 0.7783(4) 0.0429 1.0000 Uiso . H382 H -0.2355(6) -0.0673(5) 0.7409(4) 0.0429 1.0000 Uiso . H391 H -0.4301(7) -0.0234(6) 0.6251(5) 0.0495 1.0000 Uiso . H392 H -0.3060(7) -0.1073(6) 0.6361(5) 0.0495 1.0000 Uiso . H411 H -0.3792(7) 0.0434(6) 0.4765(5) 0.0566 1.0000 Uiso . H412 H -0.2366(7) -0.0083(6) 0.4785(5) 0.0566 1.0000 Uiso . H421 H -0.3291(7) 0.1910(6) 0.4403(5) 0.0465 1.0000 Uiso . H422 H -0.2890(7) 0.1544(6) 0.3630(5) 0.0465 1.0000 Uiso . H441 H -0.1864(7) 0.2820(6) 0.3777(5) 0.0516 1.0000 Uiso . H442 H -0.1397(7) 0.2320(6) 0.3105(5) 0.0516 1.0000 Uiso . H451 H 0.0130(7) 0.2884(6) 0.3322(5) 0.0552 1.0000 Uiso . H452 H 0.0518(7) 0.1691(6) 0.3828(5) 0.0552 1.0000 Uiso . H471 H 0.1035(8) 0.3279(7) 0.4222(6) 0.0870 1.0000 Uiso . H472 H 0.1821(8) 0.2158(7) 0.4489(6) 0.0870 1.0000 Uiso . H481 H 0.2136(7) 0.2539(6) 0.5634(6) 0.0663 1.0000 Uiso . H482 H 0.1287(7) 0.1785(6) 0.6027(6) 0.0663 1.0000 Uiso . H511 H -0.1065(6) 0.4375(5) 0.6169(5) 0.0430 1.0000 Uiso . H531 H 0.0711(6) 0.3790(5) 0.8435(4) 0.0396 1.0000 Uiso . H541 H 0.2297(7) 0.2657(5) 0.8160(5) 0.0494 1.0000 Uiso . H551 H 0.2156(7) 0.2265(6) 0.6968(5) 0.0482 1.0000 Uiso . H571 H -0.0405(6) 0.5185(6) 0.8172(5) 0.0599 1.0000 Uiso . H572 H -0.1325(6) 0.4511(6) 0.8692(5) 0.0599 1.0000 Uiso . H581 H -0.2169(6) 0.6157(6) 0.8503(6) 0.0671 1.0000 Uiso . H582 H -0.2103(6) 0.6529(6) 0.7427(6) 0.0671 1.0000 Uiso . H601 H -0.4343(7) 0.6556(5) 0.8592(6) 0.0589 1.0000 Uiso . H602 H -0.4100(7) 0.7208(5) 0.7545(6) 0.0589 1.0000 Uiso . H611 H -0.6076(7) 0.7113(5) 0.7672(5) 0.0425 1.0000 Uiso . H612 H -0.5334(7) 0.6462(5) 0.7174(5) 0.0425 1.0000 Uiso . H631 H -0.7493(6) 0.6246(5) 0.8174(5) 0.0414 1.0000 Uiso . H632 H -0.6855(6) 0.5588(5) 0.7658(5) 0.0414 1.0000 Uiso . H641 H -0.7161(6) 0.4810(5) 0.9532(5) 0.0473 1.0000 Uiso . H642 H -0.8006(6) 0.4767(5) 0.8847(5) 0.0473 1.0000 Uiso . H661 H -0.6770(6) 0.3105(5) 1.0226(5) 0.0428 1.0000 Uiso . H662 H -0.7358(6) 0.2995(5) 0.9453(5) 0.0428 1.0000 Uiso . H671 H -0.5775(6) 0.1589(5) 1.0273(4) 0.0412 1.0000 Uiso . H672 H -0.4864(6) 0.2292(5) 0.9884(4) 0.0412 1.0000 Uiso . H711 H -0.637(1) 0.4316(8) 0.4570(7) 0.1065 1.0000 Uiso . H712 H -0.734(1) 0.3955(8) 0.4258(7) 0.1065 1.0000 Uiso . H713 H -0.618(1) 0.4188(8) 0.3654(7) 0.1065 1.0000 Uiso . H751 H -0.5136(9) 0.4553(9) 0.6194(8) 0.1071 1.0000 Uiso . H752 H -0.6116(9) 0.4460(9) 0.6976(8) 0.1071 1.0000 Uiso . H753 H -0.6046(9) 0.3871(9) 0.6387(8) 0.1071 1.0000 Uiso . H741 H -0.8217(8) 0.4795(7) 0.6393(7) 0.0795 1.0000 Uiso . H742 H -0.8505(8) 0.5986(7) 0.5918(7) 0.0795 1.0000 Uiso . H743 H -0.8440(8) 0.5411(7) 0.5316(7) 0.0795 1.0000 Uiso . H721 H -0.5229(11) 0.2776(11) 0.5862(7) 0.1459 1.0000 Uiso . H722 H -0.5860(11) 0.1911(11) 0.6047(7) 0.1459 1.0000 Uiso . H723 H -0.4503(11) 0.1846(11) 0.5677(7) 0.1459 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.031(1) 0.0400(11) 0.029(1) -0.0187(9) -0.0025(8) -0.0124(9) F2 0.054(3) 0.068(3) 0.051(3) -0.044(3) 0.011(2) -0.018(2) F3 0.052(3) 0.097(4) 0.052(3) -0.048(3) 0.020(2) -0.045(3) F4 0.070(3) 0.090(4) 0.071(3) -0.061(3) 0.033(3) -0.051(3) F5 0.086(4) 0.071(4) 0.049(3) 0.009(3) -0.011(3) 0.007(3) F6 0.104(5) 0.157(6) 0.115(5) -0.104(5) 0.054(4) -0.100(5) F7 0.071(4) 0.091(4) 0.062(4) -0.027(3) -0.020(3) 0.022(3) P8 0.0251(9) 0.0423(12) 0.033(1) -0.0247(9) 0.0022(8) -0.0047(8) F9 0.036(2) 0.042(3) 0.066(3) -0.029(2) -0.007(2) 0.001(2) F10 0.036(2) 0.065(3) 0.073(3) -0.055(3) -0.007(2) -0.000(2) F11 0.028(3) 0.178(7) 0.164(6) -0.154(6) -0.024(3) 0.020(3) F12 0.047(3) 0.211(8) 0.176(7) -0.182(7) -0.036(4) 0.036(4) F13 0.096(5) 0.081(4) 0.063(4) 0.028(3) 0.038(3) 0.024(4) F14 0.111(5) 0.051(4) 0.169(7) -0.041(4) 0.084(5) -0.038(3) C15 0.024(3) 0.023(3) 0.021(3) -0.010(3) 0.005(3) -0.013(3) C16 0.014(3) 0.022(3) 0.025(3) -0.008(3) 0.002(3) -0.007(3) C17 0.026(4) 0.030(4) 0.032(4) -0.018(3) -0.003(3) -0.006(3) C18 0.024(4) 0.033(4) 0.031(4) -0.011(3) 0.001(3) -0.008(3) N19 0.028(3) 0.036(4) 0.023(3) -0.015(3) -0.002(2) -0.005(3) C20 0.044(4) 0.035(4) 0.020(4) -0.005(3) -0.007(3) -0.004(4) C21 0.037(4) 0.027(4) 0.028(4) -0.008(3) -0.008(3) 0.004(3) C22 0.036(4) 0.044(5) 0.034(4) -0.025(4) -0.002(3) -0.006(3) C23 0.034(4) 0.040(4) 0.020(3) -0.015(3) 0.000(3) -0.005(3) C24 0.020(3) 0.036(4) 0.036(4) -0.012(3) 0.001(3) -0.008(3) N25 0.023(3) 0.025(3) 0.040(3) -0.017(3) -0.006(3) -0.006(2) C26 0.034(4) 0.022(4) 0.032(4) -0.010(3) -0.013(3) -0.001(3) C27 0.022(3) 0.022(4) 0.040(4) -0.017(3) -0.008(3) -0.000(3) C28 0.032(4) 0.043(5) 0.043(4) -0.033(4) 0.001(3) -0.007(3) C29 0.022(3) 0.032(4) 0.032(4) -0.017(3) 0.003(3) -0.014(3) C30 0.021(3) 0.036(4) 0.027(4) -0.014(3) -0.002(3) -0.013(3) C31 0.030(4) 0.028(4) 0.019(3) -0.010(3) -0.000(3) -0.015(3) C32 0.025(4) 0.024(4) 0.032(4) -0.010(3) 0.003(3) -0.011(3) C33 0.025(4) 0.027(4) 0.029(4) -0.008(3) -0.000(3) -0.015(3) C34 0.027(4) 0.027(4) 0.030(4) -0.016(3) -0.002(3) -0.012(3) C35 0.043(4) 0.030(4) 0.024(4) -0.010(3) -0.005(3) -0.002(3) O36 0.031(3) 0.043(3) 0.033(3) -0.012(2) -0.007(2) -0.009(2) O37 0.033(3) 0.037(3) 0.027(3) -0.020(2) 0.002(2) -0.004(2) C38 0.035(4) 0.037(4) 0.032(4) -0.014(3) 0.009(3) -0.018(3) C39 0.045(5) 0.049(5) 0.029(4) -0.022(4) 0.010(3) -0.017(4) O40 0.044(3) 0.054(3) 0.022(3) -0.021(2) 0.004(2) -0.017(3) C41 0.044(5) 0.063(6) 0.034(4) -0.032(4) 0.006(3) -0.024(4) C42 0.045(5) 0.052(5) 0.028(4) -0.019(4) -0.005(3) -0.009(4) O43 0.038(3) 0.035(3) 0.020(2) -0.010(2) 0.001(2) -0.011(2) C44 0.058(5) 0.040(5) 0.025(4) -0.015(4) -0.002(4) -0.009(4) C45 0.050(5) 0.049(5) 0.030(4) -0.023(4) 0.013(3) -0.025(4) O46 0.049(3) 0.056(3) 0.030(3) -0.026(3) 0.008(2) -0.019(3) C47 0.056(6) 0.080(7) 0.058(6) -0.048(5) 0.008(4) -0.026(5) C48 0.051(5) 0.056(6) 0.056(5) -0.036(5) -0.001(4) -0.010(4) O49 0.048(3) 0.046(3) 0.039(3) -0.028(3) 0.001(2) -0.008(3) C50 0.047(5) 0.033(4) 0.029(4) -0.016(3) 0.005(3) -0.020(4) C51 0.034(4) 0.037(4) 0.031(4) -0.017(4) 0.001(3) -0.012(3) C52 0.037(4) 0.034(4) 0.024(4) -0.011(3) 0.005(3) -0.021(3) C53 0.041(4) 0.044(5) 0.024(4) -0.014(4) 0.003(3) -0.018(4) C54 0.051(5) 0.037(4) 0.029(4) -0.009(4) -0.007(4) -0.014(4) C55 0.042(5) 0.039(5) 0.037(4) -0.017(4) -0.003(4) -0.005(4) O56 0.039(3) 0.044(3) 0.035(3) -0.027(3) 0.003(2) -0.007(2) C57 0.034(4) 0.070(6) 0.048(5) -0.040(5) 0.012(4) -0.026(4) C58 0.037(4) 0.060(5) 0.063(5) -0.047(5) 0.023(4) -0.028(4) O59 0.033(3) 0.036(3) 0.042(3) -0.023(2) 0.010(2) -0.015(2) C60 0.049(5) 0.033(4) 0.058(5) -0.026(4) 0.006(4) -0.015(4) C61 0.045(5) 0.024(4) 0.041(4) -0.013(4) -0.002(4) -0.006(3) O62 0.024(2) 0.032(3) 0.040(3) -0.020(2) -0.008(2) 0.002(2) C63 0.025(4) 0.041(4) 0.037(4) -0.025(4) -0.005(3) 0.003(3) C64 0.025(4) 0.052(5) 0.045(5) -0.029(4) 0.006(3) -0.009(4) O65 0.028(3) 0.036(3) 0.038(3) -0.022(2) 0.008(2) -0.009(2) C66 0.031(4) 0.047(5) 0.035(4) -0.027(4) 0.006(3) -0.012(4) C67 0.034(4) 0.039(4) 0.022(3) -0.016(3) 0.003(3) -0.016(3) O68 0.033(3) 0.042(3) 0.027(3) -0.022(2) -0.003(2) -0.005(2) C69 0.178(16) 0.168(16) 0.106(12) -0.101(12) 0.032(11) 0.022(13) O70 0.127(8) 0.118(7) 0.080(6) -0.037(6) 0.021(5) -0.008(6) C71 0.090(8) 0.070(8) 0.085(8) -0.029(6) -0.023(7) -0.010(6) C72 0.11(1) 0.209(15) 0.057(7) -0.082(9) -0.046(7) 0.10(1) C73 0.054(6) 0.078(8) 0.077(8) -0.023(6) 0.009(6) -0.015(6) C74 0.069(7) 0.050(6) 0.093(8) -0.014(6) -0.019(6) -0.022(5) C75 0.057(7) 0.11(1) 0.11(1) -0.049(8) -0.035(7) 0.031(7) O76 0.064(6) 0.16(1) 0.153(9) 0.043(8) 0.015(6) -0.026(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . F2 . 1.619(4) yes P1 . F3 . 1.582(5) yes P1 . F4 . 1.581(5) yes P1 . F5 . 1.565(5) yes P1 . F6 . 1.547(5) yes P1 . F7 . 1.583(5) yes P8 . F9 . 1.588(4) yes P8 . F10 . 1.573(4) yes P8 . F11 . 1.572(5) yes P8 . F12 . 1.580(5) yes P8 . F13 . 1.558(6) yes P8 . F14 . 1.571(6) yes C15 . C16 . 1.477(8) yes C15 . C23 . 1.378(9) yes C15 . C27 . 1.389(8) yes C16 . C17 . 1.399(9) yes C16 . C21 . 1.395(9) yes C17 . C18 . 1.374(9) yes C17 . H171 . 1.000 no C18 . N19 . 1.345(8) yes C18 . H181 . 1.000 no N19 . C20 . 1.331(8) yes N19 . C22 . 1.495(8) yes C20 . C21 . 1.371(9) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C23 . C24 . 1.384(9) yes C23 . H231 . 1.000 no C24 . N25 . 1.334(8) yes C24 . H241 . 1.000 no N25 . C26 . 1.344(8) yes N25 . C28 . 1.491(8) yes C26 . C27 . 1.371(9) yes C26 . H261 . 1.000 no C27 . H271 . 1.000 no C28 . H281 . 1.000 no C28 . H282 . 1.000 no C28 . H283 . 1.000 no C29 . C30 . 1.390(9) yes C29 . C34 . 1.384(9) yes C29 . O68 . 1.371(8) yes C30 . C31 . 1.381(9) yes C30 . H301 . 1.000 no C31 . C32 . 1.390(9) yes C31 . O37 . 1.360(7) yes C32 . C33 . 1.410(9) yes C32 . H321 . 1.000 no C33 . C34 . 1.366(9) yes C33 . C35 . 1.515(9) yes C34 . H341 . 1.000 no C35 . O36 . 1.422(8) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no O37 . C38 . 1.432(8) yes C38 . C39 . 1.518(9) yes C38 . H381 . 1.000 no C38 . H382 . 1.000 no C39 . O40 . 1.422(8) yes C39 . H391 . 1.000 no C39 . H392 . 1.000 no O40 . C41 . 1.418(8) yes C41 . C42 . 1.48(1) yes C41 . H411 . 1.000 no C41 . H412 . 1.000 no C42 . O43 . 1.425(8) yes C42 . H421 . 1.000 no C42 . H422 . 1.000 no O43 . C44 . 1.423(8) yes C44 . C45 . 1.50(1) yes C44 . H441 . 1.000 no C44 . H442 . 1.000 no C45 . O46 . 1.422(8) yes C45 . H451 . 1.000 no C45 . H452 . 1.000 no O46 . C47 . 1.421(9) yes C47 . C48 . 1.517(11) yes C47 . H471 . 1.000 no C47 . H472 . 1.000 no C48 . O49 . 1.447(9) yes C48 . H481 . 1.000 no C48 . H482 . 1.000 no O49 . C50 . 1.377(8) yes C50 . C51 . 1.38(1) yes C50 . C55 . 1.39(1) yes C51 . C52 . 1.389(9) yes C51 . H511 . 1.000 no C52 . C53 . 1.391(9) yes C52 . O56 . 1.360(8) yes C53 . C54 . 1.37(1) yes C53 . H531 . 1.000 no C54 . C55 . 1.39(1) yes C54 . H541 . 1.000 no C55 . H551 . 1.000 no O56 . C57 . 1.433(8) yes C57 . C58 . 1.52(1) yes C57 . H571 . 1.000 no C57 . H572 . 1.000 no C58 . O59 . 1.433(8) yes C58 . H581 . 1.000 no C58 . H582 . 1.000 no O59 . C60 . 1.421(8) yes C60 . C61 . 1.49(1) yes C60 . H601 . 1.000 no C60 . H602 . 1.000 no C61 . O62 . 1.412(8) yes C61 . H611 . 1.000 no C61 . H612 . 1.000 no O62 . C63 . 1.435(8) yes C63 . C64 . 1.47(1) yes C63 . H631 . 1.000 no C63 . H632 . 1.000 no C64 . O65 . 1.426(8) yes C64 . H641 . 1.000 no C64 . H642 . 1.000 no O65 . C66 . 1.405(8) yes C66 . C67 . 1.487(9) yes C66 . H661 . 1.000 no C66 . H662 . 1.000 no C67 . O68 . 1.440(7) yes C67 . H671 . 1.000 no C67 . H672 . 1.000 no C69 . O70 . 1.386(18) yes C69 . C71 . 1.538(18) yes C69 . C72 . 1.485(18) yes C71 . H711 . 1.000 no C71 . H712 . 1.000 no C71 . H713 . 1.000 no C72 . H721 . 1.000 no C72 . H722 . 1.000 no C72 . H723 . 1.000 no C73 . C74 . 1.473(13) yes C73 . C75 . 1.487(14) yes C73 . O76 . 1.230(12) yes C74 . H741 . 1.000 no C74 . H742 . 1.000 no C74 . H743 . 1.000 no C75 . H751 . 1.000 no C75 . H752 . 1.000 no C75 . H753 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag F2 . P1 . F3 . 178.3(3) yes F2 . P1 . F4 . 88.5(2) yes F3 . P1 . F4 . 90.3(2) yes F2 . P1 . F5 . 89.2(3) yes F3 . P1 . F5 . 91.8(3) yes F4 . P1 . F5 . 88.3(3) yes F2 . P1 . F6 . 89.2(3) yes F3 . P1 . F6 . 92.0(3) yes F4 . P1 . F6 . 177.4(3) yes F5 . P1 . F6 . 92.9(4) yes F2 . P1 . F7 . 88.7(3) yes F3 . P1 . F7 . 90.2(3) yes F4 . P1 . F7 . 88.7(3) yes F5 . P1 . F7 . 176.4(4) yes F6 . P1 . F7 . 90.0(4) yes F9 . P8 . F10 . 91.9(2) yes F9 . P8 . F11 . 179.1(3) yes F10 . P8 . F11 . 88.9(2) yes F9 . P8 . F12 . 88.0(2) yes F10 . P8 . F12 . 178.1(4) yes F11 . P8 . F12 . 91.2(3) yes F9 . P8 . F13 . 88.4(3) yes F10 . P8 . F13 . 90.5(4) yes F11 . P8 . F13 . 91.3(4) yes F12 . P8 . F13 . 91.4(4) yes F9 . P8 . F14 . 88.5(3) yes F10 . P8 . F14 . 89.3(3) yes F11 . P8 . F14 . 91.8(4) yes F12 . P8 . F14 . 88.8(4) yes F13 . P8 . F14 . 176.9(4) yes C16 . C15 . C23 . 122.2(5) yes C16 . C15 . C27 . 120.6(6) yes C23 . C15 . C27 . 117.2(6) yes C15 . C16 . C17 . 120.6(6) yes C15 . C16 . C21 . 122.1(6) yes C17 . C16 . C21 . 117.1(6) yes C16 . C17 . C18 . 120.1(6) yes C16 . C17 . H171 . 119.6(4) no C18 . C17 . H171 . 120.2(4) no C17 . C18 . N19 . 120.3(6) yes C17 . C18 . H181 . 120.1(4) no N19 . C18 . H181 . 119.6(4) no C18 . N19 . C20 . 121.2(6) yes C18 . N19 . C22 . 118.7(6) yes C20 . N19 . C22 . 120.1(5) yes N19 . C20 . C21 . 120.6(6) yes N19 . C20 . H201 . 119.5(4) no C21 . C20 . H201 . 119.9(4) no C16 . C21 . C20 . 120.4(6) yes C16 . C21 . H211 . 119.4(4) no C20 . C21 . H211 . 120.2(4) no N19 . C22 . H221 . 109.8(3) no N19 . C22 . H222 . 109.1(3) no H221 . C22 . H222 . 109.476 no N19 . C22 . H223 . 109.5(4) no H221 . C22 . H223 . 109.476 no H222 . C22 . H223 . 109.476 no C15 . C23 . C24 . 121.0(6) yes C15 . C23 . H231 . 119.2(4) no C24 . C23 . H231 . 119.8(4) no C23 . C24 . N25 . 120.0(6) yes C23 . C24 . H241 . 120.5(4) no N25 . C24 . H241 . 119.5(4) no C24 . N25 . C26 . 120.6(6) yes C24 . N25 . C28 . 119.6(5) yes C26 . N25 . C28 . 119.8(5) yes N25 . C26 . C27 . 120.8(6) yes N25 . C26 . H261 . 119.4(4) no C27 . C26 . H261 . 119.8(4) no C15 . C27 . C26 . 120.3(6) yes C15 . C27 . H271 . 119.2(4) no C26 . C27 . H271 . 120.4(4) no N25 . C28 . H281 . 109.7(3) no N25 . C28 . H282 . 109.6(3) no H281 . C28 . H282 . 109.476 no N25 . C28 . H283 . 109.1(4) no H281 . C28 . H283 . 109.476 no H282 . C28 . H283 . 109.476 no C30 . C29 . C34 . 120.4(6) yes C30 . C29 . O68 . 115.6(6) yes C34 . C29 . O68 . 124.1(6) yes C29 . C30 . C31 . 120.0(6) yes C29 . C30 . H301 . 119.6(4) no C31 . C30 . H301 . 120.3(4) no C30 . C31 . C32 . 120.2(6) yes C30 . C31 . O37 . 116.2(6) yes C32 . C31 . O37 . 123.6(6) yes C31 . C32 . C33 . 118.8(6) yes C31 . C32 . H321 . 120.6(4) no C33 . C32 . H321 . 120.6(4) no C32 . C33 . C34 . 120.8(6) yes C32 . C33 . C35 . 119.5(6) yes C34 . C33 . C35 . 119.7(6) yes C29 . C34 . C33 . 119.7(6) yes C29 . C34 . H341 . 120.4(4) no C33 . C34 . H341 . 119.9(4) no C33 . C35 . O36 . 112.6(5) yes C33 . C35 . H351 . 108.1(4) no O36 . C35 . H351 . 108.4(3) no C33 . C35 . H352 . 109.0(4) no O36 . C35 . H352 . 109.2(4) no H351 . C35 . H352 . 109.467 no C31 . O37 . C38 . 117.3(5) yes O37 . C38 . C39 . 107.5(6) yes O37 . C38 . H381 . 110.1(3) no C39 . C38 . H381 . 111.5(4) no O37 . C38 . H382 . 109.4(3) no C39 . C38 . H382 . 108.8(4) no H381 . C38 . H382 . 109.467 no C38 . C39 . O40 . 107.3(6) yes C38 . C39 . H391 . 109.4(4) no O40 . C39 . H391 . 110.5(4) no C38 . C39 . H392 . 110.2(4) no O40 . C39 . H392 . 110.0(4) no H391 . C39 . H392 . 109.467 no C39 . O40 . C41 . 112.8(5) yes O40 . C41 . C42 . 109.5(6) yes O40 . C41 . H411 . 109.8(4) no C42 . C41 . H411 . 110.4(4) no O40 . C41 . H412 . 109.2(4) no C42 . C41 . H412 . 108.4(4) no H411 . C41 . H412 . 109.467 no C41 . C42 . O43 . 110.4(6) yes C41 . C42 . H421 . 108.0(4) no O43 . C42 . H421 . 109.0(4) no C41 . C42 . H422 . 110.3(4) no O43 . C42 . H422 . 109.7(3) no H421 . C42 . H422 . 109.467 no C42 . O43 . C44 . 109.8(5) yes O43 . C44 . C45 . 111.7(6) yes O43 . C44 . H441 . 108.5(4) no C45 . C44 . H441 . 107.9(4) no O43 . C44 . H442 . 109.4(3) no C45 . C44 . H442 . 109.8(4) no H441 . C44 . H442 . 109.467 no C44 . C45 . O46 . 110.3(6) yes C44 . C45 . H451 . 110.3(4) no O46 . C45 . H451 . 109.6(4) no C44 . C45 . H452 . 108.2(4) no O46 . C45 . H452 . 109.0(4) no H451 . C45 . H452 . 109.467 no C45 . O46 . C47 . 109.9(5) yes O46 . C47 . C48 . 109.3(7) yes O46 . C47 . H471 . 109.6(5) no C48 . C47 . H471 . 108.6(5) no O46 . C47 . H472 . 109.8(4) no C48 . C47 . H472 . 110.1(5) no H471 . C47 . H472 . 109.467 no C47 . C48 . O49 . 107.6(7) yes C47 . C48 . H481 . 111.2(5) no O49 . C48 . H481 . 110.1(4) no C47 . C48 . H482 . 108.7(5) no O49 . C48 . H482 . 109.6(4) no H481 . C48 . H482 . 109.467 no C48 . O49 . C50 . 116.9(6) yes O49 . C50 . C51 . 115.7(6) yes O49 . C50 . C55 . 123.7(7) yes C51 . C50 . C55 . 120.6(6) yes C50 . C51 . C52 . 120.2(7) yes C50 . C51 . H511 . 120.0(4) no C52 . C51 . H511 . 119.8(4) no C51 . C52 . C53 . 119.7(7) yes C51 . C52 . O56 . 115.7(6) yes C53 . C52 . O56 . 124.6(6) yes C52 . C53 . C54 . 119.4(7) yes C52 . C53 . H531 . 120.2(4) no C54 . C53 . H531 . 120.4(4) no C53 . C54 . C55 . 121.7(7) yes C53 . C54 . H541 . 119.2(4) no C55 . C54 . H541 . 119.1(5) no C50 . C55 . C54 . 118.4(7) yes C50 . C55 . H551 . 120.4(4) no C54 . C55 . H551 . 121.2(5) no C52 . O56 . C57 . 116.3(5) yes O56 . C57 . C58 . 108.0(6) yes O56 . C57 . H571 . 110.0(3) no C58 . C57 . H571 . 110.8(4) no O56 . C57 . H572 . 109.7(4) no C58 . C57 . H572 . 108.9(4) no H571 . C57 . H572 . 109.467 no C57 . C58 . O59 . 109.5(6) yes C57 . C58 . H581 . 110.3(4) no O59 . C58 . H581 . 109.9(3) no C57 . C58 . H582 . 108.4(4) no O59 . C58 . H582 . 109.2(4) no H581 . C58 . H582 . 109.466 no C58 . O59 . C60 . 110.1(5) yes O59 . C60 . C61 . 110.7(6) yes O59 . C60 . H601 . 108.9(4) no C61 . C60 . H601 . 108.4(4) no O59 . C60 . H602 . 109.2(4) no C61 . C60 . H602 . 110.1(4) no H601 . C60 . H602 . 109.467 no C60 . C61 . O62 . 109.9(6) yes C60 . C61 . H611 . 110.2(4) no O62 . C61 . H611 . 109.5(4) no C60 . C61 . H612 . 108.6(4) no O62 . C61 . H612 . 109.2(4) no H611 . C61 . H612 . 109.467 no C61 . O62 . C63 . 110.7(5) yes O62 . C63 . C64 . 109.3(6) yes O62 . C63 . H631 . 109.2(3) no C64 . C63 . H631 . 109.7(4) no O62 . C63 . H632 . 109.7(3) no C64 . C63 . H632 . 109.4(4) no H631 . C63 . H632 . 109.467 no C63 . C64 . O65 . 109.4(6) yes C63 . C64 . H641 . 109.4(4) no O65 . C64 . H641 . 109.2(4) no C63 . C64 . H642 . 110.0(4) no O65 . C64 . H642 . 109.5(3) no H641 . C64 . H642 . 109.467 no C64 . O65 . C66 . 112.4(5) yes O65 . C66 . C67 . 110.1(5) yes O65 . C66 . H661 . 109.3(3) no C67 . C66 . H661 . 109.9(4) no O65 . C66 . H662 . 109.2(3) no C67 . C66 . H662 . 108.9(4) no H661 . C66 . H662 . 109.467 no C66 . C67 . O68 . 108.2(5) yes C66 . C67 . H671 . 110.5(4) no O68 . C67 . H671 . 109.3(3) no C66 . C67 . H672 . 109.3(4) no O68 . C67 . H672 . 110.1(3) no H671 . C67 . H672 . 109.467 no C29 . O68 . C67 . 116.6(5) yes O70 . C69 . C71 . 116.5(14) yes O70 . C69 . C72 . 117.0(15) yes C71 . C69 . C72 . 124.6(12) yes C69 . C71 . H711 . 115.5(8) no C69 . C71 . H712 . 106.5(9) no H711 . C71 . H712 . 109.475 no C69 . C71 . H713 . 106.2(7) no H711 . C71 . H713 . 109.476 no H712 . C71 . H713 . 109.476 no C69 . C72 . H721 . 109.7(10) no C69 . C72 . H722 . 108.4(10) no H721 . C72 . H722 . 109.476 no C69 . C72 . H723 . 110.3(6) no H721 . C72 . H723 . 109.476 no H722 . C72 . H723 . 109.476 no C74 . C73 . C75 . 116.6(10) yes C74 . C73 . O76 . 119.4(10) yes C75 . C73 . O76 . 124.0(10) yes C73 . C74 . H741 . 111.5(6) no C73 . C74 . H742 . 108.1(6) no H741 . C74 . H742 . 109.476 no C73 . C74 . H743 . 108.7(6) no H741 . C74 . H743 . 109.475 no H742 . C74 . H743 . 109.476 no C73 . C75 . H751 . 108.3(7) no C73 . C75 . H752 . 110.0(7) no H751 . C75 . H752 . 109.476 no C73 . C75 . H753 . 110.1(7) no H751 . C75 . H753 . 109.476 no H752 . C75 . H753 . 109.476 no