#------------------------------------------------------------------------------ #$Date: 2023-12-05 02:57:29 +0200 (Tue, 05 Dec 2023) $ #$Revision: 288027 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247830.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7247830 loop_ _publ_author_name 'Hern\'andez-V\'azquez, Eduardo' 'Mart\'inez-Caballero, Siseth' 'Aldana-Torres, Diana' 'Estrada-Soto, Samuel' 'Nieto-Camacho, Antonio' _publ_section_title ; Discovery of phenolic 2-arylidene-isoquinolinones with antioxidant and \a-glucosidase inhibition dual action. ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D3MD00585B _journal_year 2023 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C33 H36 N2 O4' _chemical_formula_sum 'C33 H36 N2 O4' _chemical_formula_weight 524.64 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-04-08 deposited with the CCDC. 2023-11-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0933(12) _cell_length_b 16.561(3) _cell_length_c 19.628(4) _cell_measurement_reflns_used 9942 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 68.35 _cell_measurement_theta_min 3.50 _cell_volume 2955.9(9) _computing_cell_refinement 'APEX3 v2016.1 (Bruker, 2014)' _computing_data_collection 'APEX3 v2016.1 (Bruker, 2014)' _computing_data_reduction 'SAINT V8.37A (Bruker, 2014)' _computing_molecular_graphics ; Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565 ; _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Bruker, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 52.0833 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 Venture \k-geometry diffractometer 208039-01' _diffrn_measurement_method \w-scans _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_unetI/netI 0.0339 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 19335 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.320 _diffrn_reflns_theta_min 3.492 _diffrn_source 'micro-focus X-ray source' _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_T_max 0.8643 _exptl_absorpt_correction_T_min 0.8232 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'SHELXTL (Sheldrick, 2014)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.179 _exptl_crystal_description Prism _exptl_crystal_F_000 1120 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM-MeOH' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.243 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.038 _refine_ls_abs_structure_details ; Flack x determined using 1681 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 436 _refine_ls_number_reflns 5397 _refine_ls_number_restraints 308 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0527 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.4113P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1418 _refine_ls_wR_factor_ref 0.1505 _reflns_Friedel_coverage 0.765 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 4678 _reflns_number_total 5397 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3md00585b2.cif _cod_data_source_block 115MGL18 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Analytical' was changed to 'analytical' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_original_cell_volume 2956.0(9) _cod_database_code 7247830 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.837 _shelx_estimated_absorpt_t_max 0.887 _exptl_absorpt_special_details 'face indexed-numerical' _shelx_res_file ; 115MGL18.res created by SHELXL-2014/7 TITL cu_115MGL18_0m_a.res in P2(1)2(1)2(1) CELL 1.54178 9.0933 16.5615 19.6280 90.000 90.000 90.000 ZERR 4.00 0.0012 0.0028 0.0040 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 132 144 8 16 LIST 4 TEMP 25.000 SIZE 0.200 0.250 0.300 ACTA DFIX 0.85 0.01 O3 H3 DFIX 0.90 0.01 N12 H12 L.S. 10 FMAP 2 PLAN 5 HTAB EQIV $1 x-1/2, -y+1/2, -z+1 HTAB O3 O1_$1 HTAB O3 O4 EQIV $2 -x+3/2, -y+1, z-1/2 HTAB C1 O3_$2 HTAB N12 O3_$2 BOND $H CONF WGHT 0.078600 0.411300 FVAR 0.34159 0.49951 O1 4 1.014193 0.272468 0.270201 11.00000 0.09858 0.05695 = 0.05163 0.00147 -0.00427 0.00898 O2 4 0.663676 0.420307 0.275211 11.00000 0.07631 0.08213 = 0.11451 0.04139 0.00109 -0.00700 O3 4 0.624361 0.343934 0.654944 11.00000 0.08341 0.05438 = 0.05838 -0.00519 0.01189 -0.00714 H3 2 0.610868 0.296693 0.668981 11.00000 -1.20000 O4 4 0.788610 0.212826 0.630497 11.00000 0.09168 0.07205 = 0.06218 0.01824 0.00554 0.01333 C1 1 0.899505 0.478548 0.250795 11.00000 0.07055 0.05596 = 0.05524 0.01266 0.00232 -0.00067 AFIX 13 H1 2 0.931784 0.515794 0.214996 11.00000 -1.20000 AFIX 0 N2 3 0.960320 0.398469 0.235937 11.00000 0.07650 0.05718 = 0.05058 0.00548 -0.00141 0.00290 C3 1 0.977563 0.341807 0.284904 11.00000 0.06743 0.05565 = 0.05308 0.00510 -0.00142 -0.00203 C4 1 0.948429 0.368492 0.356222 11.00000 0.06716 0.05506 = 0.05043 0.00365 -0.00379 0.00174 C5 1 1.023245 0.482790 0.434326 11.00000 0.08827 0.07388 = 0.06542 -0.00207 -0.00624 -0.00943 AFIX 43 H5 2 1.040349 0.446447 0.469565 11.00000 -1.20000 AFIX 0 C6 1 1.046787 0.564121 0.444422 11.00000 0.10644 0.08278 = 0.08672 -0.01979 -0.01217 -0.01764 AFIX 43 H6 2 1.079407 0.582360 0.486609 11.00000 -1.20000 AFIX 0 C7 1 1.022319 0.619035 0.392300 11.00000 0.12086 0.05839 = 0.10371 -0.00997 -0.00494 -0.01457 AFIX 43 H7 2 1.036296 0.673964 0.399714 11.00000 -1.20000 AFIX 0 C8 1 0.977121 0.591537 0.329423 11.00000 0.08806 0.06076 = 0.08750 0.00587 0.00097 -0.00543 AFIX 43 H8 2 0.961654 0.628061 0.294153 11.00000 -1.20000 AFIX 0 C9 1 0.954613 0.509973 0.318435 11.00000 0.06770 0.05403 = 0.06582 0.00271 0.00520 -0.00039 C10 1 0.973498 0.454781 0.370928 11.00000 0.06799 0.05758 = 0.05715 0.00038 0.00012 -0.00322 C11 1 0.730360 0.476835 0.251090 11.00000 0.07397 0.06232 = 0.06032 0.00913 -0.00067 0.00009 N12 3 0.669117 0.541914 0.223704 11.00000 0.07184 0.06515 = 0.07526 0.01902 -0.00114 0.00515 H12 2 0.725525 0.583355 0.210468 11.00000 -1.20000 C13 1 0.514201 0.552989 0.214875 11.00000 0.07313 0.08261 = 0.08550 0.01530 0.00509 0.00320 AFIX 13 H13 2 0.463527 0.526592 0.252897 11.00000 -1.20000 AFIX 0 C14 1 0.475282 0.641985 0.215940 11.00000 0.09280 0.08666 = 0.09632 0.00379 -0.00038 0.01455 AFIX 23 H14A 2 0.502057 0.664433 0.259867 11.00000 -1.20000 H14B 2 0.532336 0.669744 0.181371 11.00000 -1.20000 AFIX 0 C15 1 0.315921 0.656953 0.203467 11.00000 0.09886 0.11318 = 0.16815 0.01749 0.02678 0.03435 AFIX 23 H15A 2 0.298129 0.714628 0.200989 11.00000 -1.20000 H15B 2 0.258845 0.635451 0.241068 11.00000 -1.20000 AFIX 0 C16 1 0.266859 0.617075 0.137058 11.00000 0.09514 0.11650 = 0.18818 0.00791 -0.04396 0.01048 AFIX 23 H16A 2 0.161600 0.624075 0.131640 11.00000 -1.20000 H16B 2 0.315098 0.643456 0.099014 11.00000 -1.20000 AFIX 0 C17 1 0.302285 0.529930 0.135976 11.00000 0.11593 0.10932 = 0.22425 -0.02297 -0.06900 0.00548 AFIX 23 H17A 2 0.244836 0.502576 0.170634 11.00000 -1.20000 H17B 2 0.274918 0.507632 0.092072 11.00000 -1.20000 AFIX 0 C18 1 0.460269 0.514538 0.148255 11.00000 0.08873 0.08718 = 0.14566 -0.01522 -0.02104 0.00942 AFIX 23 H18A 2 0.516937 0.536048 0.110524 11.00000 -1.20000 H18B 2 0.476989 0.456732 0.150056 11.00000 -1.20000 AFIX 0 SIMU 0.01 C19 > C27A DELU 0.005 C19 > C27A SAME 0.01 0.005 C19 C20A > C27A C19 1 0.970874 0.376940 0.164813 11.00000 0.09603 0.06194 = 0.05156 0.00796 0.00380 -0.00221 PART 1 C20 1 0.838935 0.374228 0.129812 21.00000 0.11031 0.09935 = 0.05794 0.00400 -0.00410 0.00444 AFIX 43 H20 2 0.750616 0.380153 0.153174 21.00000 -1.20000 AFIX 0 C21 1 0.838541 0.362608 0.059523 21.00000 0.11473 0.10457 = 0.06187 -0.00285 -0.00461 -0.00298 AFIX 43 H21 2 0.749704 0.364527 0.036104 21.00000 -1.20000 AFIX 0 C22 1 0.966356 0.348346 0.023798 21.00000 0.12664 0.07770 = 0.05882 0.00075 0.00026 0.00793 C23 1 1.094647 0.342147 0.060690 21.00000 0.11885 0.09444 = 0.05562 0.00741 0.01447 0.00167 AFIX 43 H23 2 1.181095 0.328042 0.038344 21.00000 -1.20000 AFIX 0 C24 1 1.098392 0.356610 0.131388 21.00000 0.10198 0.08997 = 0.05314 0.01346 0.01528 -0.01326 AFIX 43 H24 2 1.186427 0.352434 0.155245 21.00000 -1.20000 AFIX 0 C25 1 0.963672 0.338409 -0.053547 21.00000 0.14295 0.09788 = 0.06296 -0.00411 -0.00016 0.01288 AFIX 13 H25 2 0.863771 0.336141 -0.072180 21.00000 -1.20000 AFIX 0 C26 1 1.062446 0.414857 -0.084935 21.00000 0.15236 0.11778 = 0.07434 0.01887 0.01215 0.00446 AFIX 137 H26A 2 1.074184 0.407944 -0.133190 21.00000 -1.50000 H26B 2 1.157370 0.415708 -0.063541 21.00000 -1.50000 H26C 2 1.012559 0.464862 -0.076115 21.00000 -1.50000 AFIX 0 C27 1 1.057965 0.268881 -0.076072 21.00000 0.17225 0.11648 = 0.08104 -0.01460 0.01118 0.02871 AFIX 137 H27A 2 1.051494 0.263132 -0.124648 21.00000 -1.50000 H27B 2 1.024394 0.220175 -0.054593 21.00000 -1.50000 H27C 2 1.158267 0.278902 -0.063369 21.00000 -1.50000 AFIX 0 PART 2 C20A 1 0.866462 0.395343 0.117054 -21.00000 0.11379 0.08410 = 0.05144 0.01749 -0.00110 0.00519 AFIX 43 H20A 2 0.778048 0.418717 0.130404 -21.00000 -1.20000 AFIX 0 C21A 1 0.892617 0.379012 0.048092 -21.00000 0.12381 0.09584 = 0.05202 0.01358 0.00004 -0.00231 AFIX 43 H21A 2 0.818858 0.389105 0.016393 -21.00000 -1.20000 AFIX 0 C22A 1 1.025020 0.348376 0.026263 -21.00000 0.12902 0.08263 = 0.06033 0.00603 0.00948 -0.00179 C23A 1 1.128455 0.329166 0.075121 -21.00000 0.12064 0.08543 = 0.05981 0.00877 0.01963 0.00477 AFIX 43 H23A 2 1.217560 0.306714 0.061631 -21.00000 -1.20000 AFIX 0 C24A 1 1.102295 0.342747 0.144879 -21.00000 0.10485 0.07835 = 0.05989 0.01094 0.01876 0.00075 AFIX 43 H24A 2 1.172794 0.328827 0.177133 -21.00000 -1.20000 AFIX 0 C25A 1 1.055860 0.336526 -0.049739 -21.00000 0.15015 0.09429 = 0.06480 -0.00206 0.01181 -0.00083 AFIX 13 H25A 2 1.160575 0.330787 -0.060507 -21.00000 -1.20000 AFIX 0 C26A 1 0.975331 0.415006 -0.088819 -21.00000 0.21658 0.12706 = 0.07527 0.02086 -0.00159 0.02344 AFIX 137 H26D 2 0.995769 0.412730 -0.136765 -21.00000 -1.50000 H26E 2 1.013156 0.464527 -0.070402 -21.00000 -1.50000 H26F 2 0.870984 0.412675 -0.081657 -21.00000 -1.50000 AFIX 0 C27A 1 0.961303 0.269461 -0.078421 -21.00000 0.18779 0.12845 = 0.08132 -0.01945 0.00074 -0.02012 AFIX 137 H27D 2 0.979420 0.264260 -0.126405 -21.00000 -1.50000 H27E 2 0.859466 0.281978 -0.071022 -21.00000 -1.50000 H27F 2 0.985035 0.219600 -0.056032 -21.00000 -1.50000 AFIX 0 PART 0 C28 1 0.898088 0.312381 0.399448 11.00000 0.06974 0.05277 = 0.05538 0.00158 -0.00375 0.00158 AFIX 43 H28 2 0.907513 0.259321 0.384566 11.00000 -1.20000 AFIX 0 C29 1 0.829980 0.322135 0.467083 11.00000 0.06699 0.05112 = 0.05287 0.00269 -0.00152 -0.00173 C30 1 0.846738 0.261576 0.515894 11.00000 0.06749 0.05325 = 0.05771 0.00106 0.00164 0.00500 AFIX 43 H30 2 0.904866 0.216832 0.506178 11.00000 -1.20000 AFIX 0 C31 1 0.777691 0.267317 0.578777 11.00000 0.06462 0.05388 = 0.05316 0.00554 -0.00413 -0.00029 C32 1 0.688391 0.333905 0.592753 11.00000 0.06180 0.05023 = 0.05276 -0.00243 -0.00062 -0.00640 C33 1 0.668957 0.392681 0.543835 11.00000 0.06570 0.05062 = 0.07141 -0.00008 0.00305 0.00570 AFIX 43 H33 2 0.608135 0.436551 0.552825 11.00000 -1.20000 AFIX 0 C34 1 0.739092 0.386969 0.481546 11.00000 0.07314 0.05858 = 0.06129 0.01181 -0.00162 0.00597 AFIX 43 H34 2 0.725086 0.427079 0.449027 11.00000 -1.20000 AFIX 0 C35 1 0.883320 0.146372 0.621853 11.00000 0.13997 0.09765 = 0.10727 0.04460 0.02789 0.05278 AFIX 137 H35A 2 0.851441 0.114970 0.583486 11.00000 -1.50000 H35B 2 0.881452 0.113497 0.662127 11.00000 -1.50000 H35C 2 0.981654 0.165332 0.614052 11.00000 -1.50000 AFIX 0 HKLF 4 REM cu_115MGL18_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0527 for 4678 Fo > 4sig(Fo) and 0.0596 for all 5397 data REM 436 parameters refined using 308 restraints END WGHT 0.0788 0.4096 REM Instructions for potential hydrogen bonds HTAB O3 O1_$1 HTAB O3 O4 HTAB C1 O3_$2 HTAB N12 O3_$2 HTAB C20 O2 REM Highest difference peak 0.243, deepest hole -0.226, 1-sigma level 0.038 Q1 1 0.9110 0.1722 0.7645 11.00000 0.05 0.22 Q2 1 0.3870 0.6308 0.2423 11.00000 0.05 0.17 Q3 1 0.4127 0.4993 0.2107 11.00000 0.05 0.17 Q4 1 0.5432 0.6791 0.2493 11.00000 0.05 0.16 Q5 1 0.4020 0.6595 0.1686 11.00000 0.05 0.16 ; _shelx_res_checksum 72813 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.0142(3) 0.27247(13) 0.27020(12) 0.0691(6) Uani 1 1 d . . . . . O2 O 0.6637(3) 0.42031(18) 0.27521(17) 0.0910(9) Uani 1 1 d . . . . . O3 O 0.6244(3) 0.34393(14) 0.65494(12) 0.0654(6) Uani 1 1 d D . . . . H3 H 0.611(5) 0.2967(12) 0.669(2) 0.078 Uiso 1 1 d D U . . . O4 O 0.7886(3) 0.21283(16) 0.63050(13) 0.0753(7) Uani 1 1 d . . . . . C1 C 0.8995(4) 0.47855(19) 0.25080(17) 0.0606(8) Uani 1 1 d . . . . . H1 H 0.9318 0.5158 0.2150 0.073 Uiso 1 1 calc R U . . . N2 N 0.9603(3) 0.39847(16) 0.23594(13) 0.0614(7) Uani 1 1 d . . . . . C3 C 0.9776(4) 0.34181(19) 0.28490(16) 0.0587(7) Uani 1 1 d . . . . . C4 C 0.9484(4) 0.36849(19) 0.35622(16) 0.0575(7) Uani 1 1 d . . . . . C5 C 1.0232(5) 0.4828(2) 0.4343(2) 0.0759(10) Uani 1 1 d . . . . . H5 H 1.0403 0.4464 0.4696 0.091 Uiso 1 1 calc R U . . . C6 C 1.0468(6) 0.5641(3) 0.4444(2) 0.0920(13) Uani 1 1 d . . . . . H6 H 1.0794 0.5824 0.4866 0.110 Uiso 1 1 calc R U . . . C7 C 1.0223(6) 0.6190(3) 0.3923(3) 0.0943(14) Uani 1 1 d . . . . . H7 H 1.0363 0.6740 0.3997 0.113 Uiso 1 1 calc R U . . . C8 C 0.9771(5) 0.5915(2) 0.3294(2) 0.0788(10) Uani 1 1 d . . . . . H8 H 0.9617 0.6281 0.2942 0.095 Uiso 1 1 calc R U . . . C9 C 0.9546(4) 0.5100(2) 0.31843(18) 0.0625(8) Uani 1 1 d . . . . . C10 C 0.9735(4) 0.45478(19) 0.37093(17) 0.0609(8) Uani 1 1 d . . . . . C11 C 0.7304(4) 0.4768(2) 0.25109(18) 0.0655(8) Uani 1 1 d . . . . . N12 N 0.6691(4) 0.54191(18) 0.22370(17) 0.0707(8) Uani 1 1 d D . . . . H12 H 0.726(4) 0.5834(19) 0.210(2) 0.085 Uiso 1 1 d D U . . . C13 C 0.5142(5) 0.5530(3) 0.2149(2) 0.0804(11) Uani 1 1 d . . . . . H13 H 0.4635 0.5266 0.2529 0.096 Uiso 1 1 calc R U . . . C14 C 0.4753(5) 0.6420(3) 0.2159(3) 0.0919(12) Uani 1 1 d . . . . . H14A H 0.5021 0.6644 0.2599 0.110 Uiso 1 1 calc R U . . . H14B H 0.5323 0.6697 0.1814 0.110 Uiso 1 1 calc R U . . . C15 C 0.3159(7) 0.6570(4) 0.2035(4) 0.127(2) Uani 1 1 d . . . . . H15A H 0.2981 0.7146 0.2010 0.152 Uiso 1 1 calc R U . . . H15B H 0.2588 0.6355 0.2411 0.152 Uiso 1 1 calc R U . . . C16 C 0.2669(7) 0.6171(4) 0.1371(4) 0.133(2) Uani 1 1 d . . . . . H16A H 0.1616 0.6241 0.1316 0.160 Uiso 1 1 calc R U . . . H16B H 0.3151 0.6435 0.0990 0.160 Uiso 1 1 calc R U . . . C17 C 0.3023(8) 0.5299(4) 0.1360(5) 0.150(3) Uani 1 1 d . . . . . H17A H 0.2448 0.5026 0.1706 0.180 Uiso 1 1 calc R U . . . H17B H 0.2749 0.5076 0.0921 0.180 Uiso 1 1 calc R U . . . C18 C 0.4603(6) 0.5145(3) 0.1483(3) 0.1072(16) Uani 1 1 d . . . . . H18A H 0.5169 0.5360 0.1105 0.129 Uiso 1 1 calc R U . . . H18B H 0.4770 0.4567 0.1501 0.129 Uiso 1 1 calc R U . . . C19 C 0.9709(5) 0.3769(2) 0.16481(17) 0.0698(8) Uani 1 1 d D U . . . C20 C 0.8389(10) 0.3742(8) 0.1298(4) 0.089(3) Uani 0.500(10) 1 d D U P A 1 H20 H 0.7506 0.3802 0.1532 0.107 Uiso 0.500(10) 1 calc R U P A 1 C21 C 0.8385(13) 0.3626(8) 0.0595(4) 0.094(2) Uani 0.500(10) 1 d D U P A 1 H21 H 0.7497 0.3645 0.0361 0.112 Uiso 0.500(10) 1 calc R U P A 1 C22 C 0.9664(14) 0.3483(8) 0.0238(3) 0.088(2) Uani 0.500(10) 1 d D U P A 1 C23 C 1.0946(12) 0.3421(10) 0.0607(4) 0.090(2) Uani 0.500(10) 1 d D U P A 1 H23 H 1.1811 0.3280 0.0383 0.108 Uiso 0.500(10) 1 calc R U P A 1 C24 C 1.0984(10) 0.3566(11) 0.1314(4) 0.082(3) Uani 0.500(10) 1 d D U P A 1 H24 H 1.1864 0.3524 0.1552 0.098 Uiso 0.500(10) 1 calc R U P A 1 C25 C 0.9637(12) 0.3384(6) -0.0535(3) 0.101(3) Uani 0.500(10) 1 d D U P A 1 H25 H 0.8638 0.3361 -0.0722 0.122 Uiso 0.500(10) 1 calc R U P A 1 C26 C 1.0624(18) 0.4149(7) -0.0849(7) 0.115(4) Uani 0.500(10) 1 d D U P A 1 H26A H 1.0742 0.4079 -0.1332 0.172 Uiso 0.500(10) 1 calc R U P A 1 H26B H 1.1574 0.4157 -0.0635 0.172 Uiso 0.500(10) 1 calc R U P A 1 H26C H 1.0126 0.4649 -0.0761 0.172 Uiso 0.500(10) 1 calc R U P A 1 C27 C 1.0580(19) 0.2689(7) -0.0761(7) 0.123(4) Uani 0.500(10) 1 d D U P A 1 H27A H 1.0515 0.2631 -0.1246 0.185 Uiso 0.500(10) 1 calc R U P A 1 H27B H 1.0244 0.2202 -0.0546 0.185 Uiso 0.500(10) 1 calc R U P A 1 H27C H 1.1583 0.2789 -0.0634 0.185 Uiso 0.500(10) 1 calc R U P A 1 C20A C 0.8665(11) 0.3953(7) 0.1171(4) 0.083(3) Uani 0.500(10) 1 d D U P A 2 H20A H 0.7780 0.4187 0.1304 0.100 Uiso 0.500(10) 1 calc R U P A 2 C21A C 0.8926(14) 0.3790(7) 0.0481(4) 0.091(2) Uani 0.500(10) 1 d D U P A 2 H21A H 0.8189 0.3891 0.0164 0.109 Uiso 0.500(10) 1 calc R U P A 2 C22A C 1.0250(15) 0.3484(8) 0.0263(3) 0.091(2) Uani 0.500(10) 1 d D U P A 2 C23A C 1.1285(12) 0.3292(9) 0.0751(4) 0.089(2) Uani 0.500(10) 1 d D U P A 2 H23A H 1.2176 0.3067 0.0616 0.106 Uiso 0.500(10) 1 calc R U P A 2 C24A C 1.1023(11) 0.3427(11) 0.1449(4) 0.081(3) Uani 0.500(10) 1 d D U P A 2 H24A H 1.1728 0.3288 0.1771 0.097 Uiso 0.500(10) 1 calc R U P A 2 C25A C 1.0559(13) 0.3365(6) -0.0497(3) 0.103(3) Uani 0.500(10) 1 d D U P A 2 H25A H 1.1606 0.3308 -0.0605 0.124 Uiso 0.500(10) 1 calc R U P A 2 C26A C 0.975(2) 0.4150(8) -0.0888(7) 0.140(5) Uani 0.500(10) 1 d D U P A 2 H26D H 0.9958 0.4127 -0.1368 0.209 Uiso 0.500(10) 1 calc R U P A 2 H26E H 1.0132 0.4645 -0.0704 0.209 Uiso 0.500(10) 1 calc R U P A 2 H26F H 0.8710 0.4127 -0.0817 0.209 Uiso 0.500(10) 1 calc R U P A 2 C27A C 0.961(2) 0.2695(8) -0.0784(7) 0.133(5) Uani 0.500(10) 1 d D U P A 2 H27D H 0.9794 0.2643 -0.1264 0.199 Uiso 0.500(10) 1 calc R U P A 2 H27E H 0.8595 0.2820 -0.0710 0.199 Uiso 0.500(10) 1 calc R U P A 2 H27F H 0.9850 0.2196 -0.0560 0.199 Uiso 0.500(10) 1 calc R U P A 2 C28 C 0.8981(4) 0.3124(2) 0.39945(16) 0.0593(8) Uani 1 1 d . . . . . H28 H 0.9075 0.2593 0.3846 0.071 Uiso 1 1 calc R U . . . C29 C 0.8300(4) 0.32214(18) 0.46708(16) 0.0570(7) Uani 1 1 d . . . . . C30 C 0.8467(4) 0.26158(19) 0.51589(17) 0.0595(8) Uani 1 1 d . . . . . H30 H 0.9049 0.2168 0.5062 0.071 Uiso 1 1 calc R U . . . C31 C 0.7777(4) 0.26732(19) 0.57878(16) 0.0572(7) Uani 1 1 d . . . . . C32 C 0.6884(4) 0.33390(18) 0.59275(16) 0.0549(7) Uani 1 1 d . . . . . C33 C 0.6690(4) 0.39268(19) 0.54384(18) 0.0626(8) Uani 1 1 d . . . . . H33 H 0.6081 0.4366 0.5528 0.075 Uiso 1 1 calc R U . . . C34 C 0.7391(4) 0.3870(2) 0.48155(18) 0.0643(8) Uani 1 1 d . . . . . H34 H 0.7251 0.4271 0.4490 0.077 Uiso 1 1 calc R U . . . C35 C 0.8833(7) 0.1464(3) 0.6219(3) 0.115(2) Uani 1 1 d . . . . . H35A H 0.8514 0.1150 0.5835 0.172 Uiso 1 1 calc R U . . . H35B H 0.8815 0.1135 0.6621 0.172 Uiso 1 1 calc R U . . . H35C H 0.9817 0.1653 0.6141 0.172 Uiso 1 1 calc R U . . . 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 0.0986(18) 0.0570(13) 0.0516(12) 0.0015(10) -0.0043(12) 0.0090(12) O2 0.0763(16) 0.0821(17) 0.115(2) 0.0414(17) 0.0011(16) -0.0070(14) O3 0.0834(16) 0.0544(12) 0.0584(13) -0.0052(10) 0.0119(11) -0.0071(11) O4 0.0917(18) 0.0721(14) 0.0622(14) 0.0182(12) 0.0055(13) 0.0133(13) C1 0.0705(19) 0.0560(17) 0.0552(18) 0.0127(14) 0.0023(15) -0.0007(15) N2 0.0765(17) 0.0572(14) 0.0506(14) 0.0055(11) -0.0014(13) 0.0029(13) C3 0.0674(18) 0.0557(17) 0.0531(17) 0.0051(14) -0.0014(14) -0.0020(14) C4 0.0672(19) 0.0551(16) 0.0504(16) 0.0036(13) -0.0038(14) 0.0017(14) C5 0.088(3) 0.074(2) 0.065(2) -0.0021(17) -0.0062(19) -0.009(2) C6 0.106(3) 0.083(3) 0.087(3) -0.020(2) -0.012(3) -0.018(2) C7 0.121(4) 0.058(2) 0.104(3) -0.010(2) -0.005(3) -0.015(2) C8 0.088(3) 0.061(2) 0.088(3) 0.0059(19) 0.001(2) -0.0054(19) C9 0.0677(19) 0.0540(17) 0.0658(19) 0.0027(14) 0.0052(16) -0.0004(15) C10 0.0680(19) 0.0576(16) 0.0572(18) 0.0004(14) 0.0001(15) -0.0032(15) C11 0.074(2) 0.0623(19) 0.0603(19) 0.0091(15) -0.0007(16) 0.0001(16) N12 0.0718(18) 0.0651(17) 0.0753(19) 0.0190(15) -0.0011(15) 0.0052(14) C13 0.073(2) 0.083(2) 0.086(3) 0.015(2) 0.005(2) 0.0032(19) C14 0.093(3) 0.087(3) 0.096(3) 0.004(2) 0.000(3) 0.015(2) C15 0.099(4) 0.113(4) 0.168(6) 0.017(4) 0.027(4) 0.034(3) C16 0.095(4) 0.116(4) 0.188(7) 0.008(5) -0.044(4) 0.010(3) C17 0.116(5) 0.109(4) 0.224(8) -0.023(5) -0.069(5) 0.005(3) C18 0.089(3) 0.087(3) 0.146(5) -0.015(3) -0.021(3) 0.009(2) C19 0.096(2) 0.0619(18) 0.0516(17) 0.0080(14) 0.0038(15) -0.0022(17) C20 0.110(4) 0.099(6) 0.058(4) 0.004(4) -0.004(4) 0.004(5) C21 0.115(5) 0.105(5) 0.062(4) -0.003(4) -0.005(3) -0.003(5) C22 0.127(5) 0.078(4) 0.059(3) 0.001(3) 0.000(3) 0.008(5) C23 0.119(5) 0.094(5) 0.056(4) 0.007(4) 0.014(3) 0.002(4) C24 0.102(4) 0.090(6) 0.053(4) 0.013(5) 0.015(3) -0.013(4) C25 0.143(7) 0.098(5) 0.063(3) -0.004(4) 0.000(4) 0.013(5) C26 0.152(11) 0.118(6) 0.074(6) 0.019(5) 0.012(7) 0.004(7) C27 0.172(12) 0.116(6) 0.081(6) -0.015(6) 0.011(8) 0.029(8) C20A 0.114(5) 0.084(5) 0.051(4) 0.017(4) -0.001(3) 0.005(4) C21A 0.124(5) 0.096(5) 0.052(3) 0.014(3) 0.000(4) -0.002(4) C22A 0.129(6) 0.083(4) 0.060(3) 0.006(3) 0.009(3) -0.002(5) C23A 0.121(5) 0.085(5) 0.060(4) 0.009(4) 0.020(3) 0.005(4) C24A 0.105(4) 0.078(6) 0.060(4) 0.011(5) 0.019(4) 0.001(4) C25A 0.150(7) 0.094(5) 0.065(4) -0.002(4) 0.012(4) -0.001(5) C26A 0.217(15) 0.127(7) 0.075(6) 0.021(6) -0.002(10) 0.023(9) C27A 0.188(13) 0.128(7) 0.081(6) -0.019(6) 0.001(9) -0.020(9) C28 0.0697(19) 0.0528(16) 0.0554(17) 0.0016(13) -0.0037(15) 0.0016(15) C29 0.0670(18) 0.0511(15) 0.0529(17) 0.0027(13) -0.0015(14) -0.0017(14) C30 0.0675(19) 0.0532(16) 0.0577(18) 0.0011(14) 0.0016(14) 0.0050(14) C31 0.0646(18) 0.0539(16) 0.0532(17) 0.0055(13) -0.0041(14) -0.0003(14) C32 0.0618(17) 0.0502(15) 0.0528(16) -0.0024(13) -0.0006(14) -0.0064(14) C33 0.0657(19) 0.0506(16) 0.071(2) -0.0001(15) 0.0031(16) 0.0057(14) C34 0.073(2) 0.0586(18) 0.0613(19) 0.0118(15) -0.0016(15) 0.0060(15) C35 0.140(5) 0.098(3) 0.107(4) 0.045(3) 0.028(3) 0.053(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C32 O3 H3 104(3) . . ? C31 O4 C35 118.2(3) . . ? N2 C1 C9 111.2(3) . . ? N2 C1 C11 111.2(3) . . ? C9 C1 C11 109.5(3) . . ? N2 C1 H1 108.3 . . ? C9 C1 H1 108.3 . . ? C11 C1 H1 108.3 . . ? C3 N2 C19 120.5(3) . . ? C3 N2 C1 122.0(3) . . ? C19 N2 C1 116.1(3) . . ? O1 C3 N2 120.8(3) . . ? O1 C3 C4 123.0(3) . . ? N2 C3 C4 116.2(3) . . ? C28 C4 C10 126.9(3) . . ? C28 C4 C3 116.7(3) . . ? C10 C4 C3 116.3(3) . . ? C6 C5 C10 120.1(4) . . ? C6 C5 H5 120.0 . . ? C10 C5 H5 120.0 . . ? C5 C6 C7 120.7(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.5(4) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.4(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C10 120.6(3) . . ? C8 C9 C1 121.5(3) . . ? C10 C9 C1 117.8(3) . . ? C9 C10 C5 118.7(3) . . ? C9 C10 C4 118.3(3) . . ? C5 C10 C4 122.9(3) . . ? O2 C11 N12 125.2(4) . . ? O2 C11 C1 121.1(3) . . ? N12 C11 C1 113.8(3) . . ? C11 N12 C13 124.5(3) . . ? C11 N12 H12 120(3) . . ? C13 N12 H12 116(3) . . ? N12 C13 C14 110.7(4) . . ? N12 C13 C18 111.4(4) . . ? C14 C13 C18 109.9(4) . . ? N12 C13 H13 108.3 . . ? C14 C13 H13 108.3 . . ? C18 C13 H13 108.3 . . ? C15 C14 C13 112.7(5) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 C16 110.6(5) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 111.7(6) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 112.2(5) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C13 112.2(6) . . ? C17 C18 H18A 109.2 . . ? C13 C18 H18A 109.2 . . ? C17 C18 H18B 109.2 . . ? C13 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C20A C19 C24A 119.9(5) . . ? C24 C19 C20 119.1(5) . . ? C20A C19 N2 124.1(5) . . ? C24 C19 N2 125.3(5) . . ? C24A C19 N2 115.7(5) . . ? C20 C19 N2 115.5(5) . . ? C19 C20 C21 119.9(7) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 121.7(8) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C23 C22 C21 117.4(6) . . ? C23 C22 C25 121.9(8) . . ? C21 C22 C25 120.7(9) . . ? C22 C23 C24 121.7(7) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C19 C24 C23 119.4(7) . . ? C19 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C27 C25 C22 111.5(7) . . ? C27 C25 C26 99.5(8) . . ? C22 C25 C26 106.0(6) . . ? C27 C25 H25 112.9 . . ? C22 C25 H25 112.9 . . ? C26 C25 H25 112.9 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C19 C20A C21A 120.1(7) . . ? C19 C20A H20A 120.0 . . ? C21A C20A H20A 120.0 . . ? C22A C21A C20A 121.4(7) . . ? C22A C21A H21A 119.3 . . ? C20A C21A H21A 119.3 . . ? C21A C22A C23A 117.7(6) . . ? C21A C22A C25A 120.8(8) . . ? C23A C22A C25A 121.5(9) . . ? C22A C23A C24A 121.6(7) . . ? C22A C23A H23A 119.2 . . ? C24A C23A H23A 119.2 . . ? C19 C24A C23A 119.2(7) . . ? C19 C24A H24A 120.4 . . ? C23A C24A H24A 120.4 . . ? C27A C25A C22A 110.6(7) . . ? C27A C25A C26A 98.7(8) . . ? C22A C25A C26A 105.4(6) . . ? C27A C25A H25A 113.6 . . ? C22A C25A H25A 113.6 . . ? C26A C25A H25A 113.6 . . ? C25A C26A H26D 109.5 . . ? C25A C26A H26E 109.5 . . ? H26D C26A H26E 109.5 . . ? C25A C26A H26F 109.5 . . ? H26D C26A H26F 109.5 . . ? H26E C26A H26F 109.5 . . ? C25A C27A H27D 109.5 . . ? C25A C27A H27E 109.5 . . ? H27D C27A H27E 109.5 . . ? C25A C27A H27F 109.5 . . ? H27D C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? C4 C28 C29 129.7(3) . . ? C4 C28 H28 115.2 . . ? C29 C28 H28 115.2 . . ? C34 C29 C30 118.8(3) . . ? C34 C29 C28 121.4(3) . . ? C30 C29 C28 119.6(3) . . ? C31 C30 C29 120.8(3) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? O4 C31 C30 125.8(3) . . ? O4 C31 C32 114.8(3) . . ? C30 C31 C32 119.5(3) . . ? O3 C32 C33 118.9(3) . . ? O3 C32 C31 121.4(3) . . ? C33 C32 C31 119.7(3) . . ? C32 C33 C34 120.6(3) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C33 C34 C29 120.7(3) . . ? C33 C34 H34 119.7 . . ? C29 C34 H34 119.7 . . ? O4 C35 H35A 109.5 . . ? O4 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O4 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? 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 C3 1.230(4) . ? O2 C11 1.212(4) . ? O3 C32 1.363(4) . ? O3 H3 0.838(14) . ? O4 C31 1.362(4) . ? O4 C35 1.408(5) . ? C1 N2 1.466(4) . ? C1 C9 1.511(5) . ? C1 C11 1.538(5) . ? C1 H1 0.9800 . ? N2 C3 1.352(4) . ? N2 C19 1.444(4) . ? C3 C4 1.492(5) . ? C4 C28 1.339(5) . ? C4 C10 1.476(5) . ? C5 C6 1.378(6) . ? C5 C10 1.403(5) . ? C5 H5 0.9300 . ? C6 C7 1.387(7) . ? C6 H6 0.9300 . ? C7 C8 1.378(6) . ? C7 H7 0.9300 . ? C8 C9 1.383(5) . ? C8 H8 0.9300 . ? C9 C10 1.388(5) . ? C11 N12 1.327(4) . ? N12 C13 1.431(5) . ? N12 H12 0.895(14) . ? C13 C14 1.516(6) . ? C13 C18 1.535(7) . ? C13 H13 0.9800 . ? C14 C15 1.490(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.528(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.479(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.479(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20A 1.369(8) . ? C19 C24 1.374(9) . ? C19 C24A 1.379(9) . ? C19 C20 1.383(9) . ? C20 C21 1.393(10) . ? C20 H20 0.9300 . ? C21 C22 1.378(12) . ? C21 H21 0.9300 . ? C22 C23 1.377(11) . ? C22 C25 1.527(8) . ? C23 C24 1.409(9) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C27 1.502(12) . ? C25 C26 1.670(12) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C20A C21A 1.401(10) . ? C20A H20A 0.9300 . ? C21A C22A 1.375(12) . ? C21A H21A 0.9300 . ? C22A C23A 1.380(11) . ? C22A C25A 1.531(9) . ? C23A C24A 1.408(10) . ? C23A H23A 0.9300 . ? C24A H24A 0.9300 . ? C25A C27A 1.513(12) . ? C25A C26A 1.677(12) . ? C25A H25A 0.9800 . ? C26A H26D 0.9600 . ? C26A H26E 0.9600 . ? C26A H26F 0.9600 . ? C27A H27D 0.9600 . ? C27A H27E 0.9600 . ? C27A H27F 0.9600 . ? C28 C29 1.474(5) . ? C28 H28 0.9300 . ? C29 C34 1.384(5) . ? C29 C30 1.395(4) . ? C30 C31 1.388(5) . ? C30 H30 0.9300 . ? C31 C32 1.397(5) . ? C32 C33 1.379(5) . ? C33 C34 1.382(5) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O1 0.838(14) 1.87(3) 2.623(3) 148(4) 2_456 O3 H3 O4 0.838(14) 2.26(4) 2.679(4) 111(3) . C1 H1 O3 0.98 2.65 3.497(4) 144.3 4_664 N12 H12 O3 0.895(14) 2.12(2) 2.987(4) 162(4) 4_664 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 N2 C3 38.9(4) . . . . ? C11 C1 N2 C3 -83.4(4) . . . . ? C9 C1 N2 C19 -154.1(3) . . . . ? C11 C1 N2 C19 83.6(4) . . . . ? C19 N2 C3 O1 5.9(5) . . . . ? C1 N2 C3 O1 172.3(3) . . . . ? C19 N2 C3 C4 -173.6(3) . . . . ? C1 N2 C3 C4 -7.2(5) . . . . ? O1 C3 C4 C28 -29.5(5) . . . . ? N2 C3 C4 C28 150.0(3) . . . . ? O1 C3 C4 C10 152.5(3) . . . . ? N2 C3 C4 C10 -28.0(5) . . . . ? C10 C5 C6 C7 -0.2(8) . . . . ? C5 C6 C7 C8 -1.4(8) . . . . ? C6 C7 C8 C9 0.7(8) . . . . ? C7 C8 C9 C10 1.7(7) . . . . ? C7 C8 C9 C1 177.6(4) . . . . ? N2 C1 C9 C8 147.4(4) . . . . ? C11 C1 C9 C8 -89.3(4) . . . . ? N2 C1 C9 C10 -36.5(4) . . . . ? C11 C1 C9 C10 86.8(4) . . . . ? C8 C9 C10 C5 -3.3(6) . . . . ? C1 C9 C10 C5 -179.4(4) . . . . ? C8 C9 C10 C4 -179.8(4) . . . . ? C1 C9 C10 C4 4.1(5) . . . . ? C6 C5 C10 C9 2.6(6) . . . . ? C6 C5 C10 C4 178.9(4) . . . . ? C28 C4 C10 C9 -148.5(4) . . . . ? C3 C4 C10 C9 29.2(5) . . . . ? C28 C4 C10 C5 35.1(6) . . . . ? C3 C4 C10 C5 -147.2(4) . . . . ? N2 C1 C11 O2 39.2(5) . . . . ? C9 C1 C11 O2 -84.0(4) . . . . ? N2 C1 C11 N12 -141.4(3) . . . . ? C9 C1 C11 N12 95.4(4) . . . . ? O2 C11 N12 C13 -3.9(7) . . . . ? C1 C11 N12 C13 176.7(4) . . . . ? C11 N12 C13 C14 152.2(4) . . . . ? C11 N12 C13 C18 -85.2(5) . . . . ? N12 C13 C14 C15 177.1(4) . . . . ? C18 C13 C14 C15 53.7(6) . . . . ? C13 C14 C15 C16 -54.6(7) . . . . ? C14 C15 C16 C17 54.7(8) . . . . ? C15 C16 C17 C18 -55.4(10) . . . . ? C16 C17 C18 C13 55.1(10) . . . . ? N12 C13 C18 C17 -176.3(5) . . . . ? C14 C13 C18 C17 -53.3(7) . . . . ? C3 N2 C19 C20A 127.8(7) . . . . ? C1 N2 C19 C20A -39.4(8) . . . . ? C3 N2 C19 C24 -71.6(11) . . . . ? C1 N2 C19 C24 121.3(11) . . . . ? C3 N2 C19 C24A -58.7(10) . . . . ? C1 N2 C19 C24A 134.2(9) . . . . ? C3 N2 C19 C20 105.8(8) . . . . ? C1 N2 C19 C20 -61.3(8) . . . . ? C24 C19 C20 C21 -9.3(16) . . . . ? N2 C19 C20 C21 173.1(9) . . . . ? C19 C20 C21 C22 4.3(18) . . . . ? C20 C21 C22 C23 3.0(19) . . . . ? C20 C21 C22 C25 -178.1(11) . . . . ? C21 C22 C23 C24 -5(2) . . . . ? C25 C22 C23 C24 175.7(13) . . . . ? C20 C19 C24 C23 7.0(19) . . . . ? N2 C19 C24 C23 -175.7(10) . . . . ? C22 C23 C24 C19 0(2) . . . . ? C23 C22 C25 C27 42.8(16) . . . . ? C21 C22 C25 C27 -136.0(13) . . . . ? C23 C22 C25 C26 -64.5(15) . . . . ? C21 C22 C25 C26 116.6(13) . . . . ? C24A C19 C20A C21A 0.4(15) . . . . ? N2 C19 C20A C21A 173.7(7) . . . . ? C19 C20A C21A C22A -3.4(16) . . . . ? C20A C21A C22A C23A 4.2(18) . . . . ? C20A C21A C22A C25A -175.6(10) . . . . ? C21A C22A C23A C24A -2(2) . . . . ? C25A C22A C23A C24A 177.7(13) . . . . ? C20A C19 C24A C23A 1.6(19) . . . . ? N2 C19 C24A C23A -172.3(11) . . . . ? C22A C23A C24A C19 -1(2) . . . . ? C21A C22A C25A C27A -68.8(14) . . . . ? C23A C22A C25A C27A 111.5(15) . . . . ? C21A C22A C25A C26A 37.0(15) . . . . ? C23A C22A C25A C26A -142.8(15) . . . . ? C10 C4 C28 C29 12.3(6) . . . . ? C3 C4 C28 C29 -165.4(3) . . . . ? C4 C28 C29 C34 35.3(6) . . . . ? C4 C28 C29 C30 -150.3(4) . . . . ? C34 C29 C30 C31 -2.2(5) . . . . ? C28 C29 C30 C31 -176.7(3) . . . . ? C35 O4 C31 C30 3.4(6) . . . . ? C35 O4 C31 C32 -176.4(4) . . . . ? C29 C30 C31 O4 -178.6(3) . . . . ? C29 C30 C31 C32 1.1(5) . . . . ? O4 C31 C32 O3 3.0(4) . . . . ? C30 C31 C32 O3 -176.7(3) . . . . ? O4 C31 C32 C33 -179.7(3) . . . . ? C30 C31 C32 C33 0.5(5) . . . . ? O3 C32 C33 C34 176.2(3) . . . . ? C31 C32 C33 C34 -1.1(5) . . . . ? C32 C33 C34 C29 0.1(5) . . . . ? C30 C29 C34 C33 1.6(5) . . . . ? C28 C29 C34 C33 176.0(3) . . . . ?