#------------------------------------------------------------------------------ #$Date: 2020-02-27 04:09:06 +0200 (Thu, 27 Feb 2020) $ #$Revision: 248474 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557383.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_1557383 loop_ _publ_author_name 'Kim, Inwon' 'Im, Honggu' 'Lee, Hyeonyeong' 'Hong, Sungwoo' _publ_section_title ; N-Heterocyclic Carbene-Catalyzed Deaminative Cross-Coupling of Aldehydes with Katritzky Pyridinium Salts ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC00225A _journal_year 2020 _chemical_formula_sum 'C20 H21 N O4' _chemical_formula_weight 339.38 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-08 deposited with the CCDC. 2020-02-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.605(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.2314(5) _cell_length_b 19.6394(11) _cell_length_c 19.9121(10) _cell_measurement_reflns_used 9360 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 2.59 _cell_volume 3602.9(3) _computing_cell_refinement 'Bruker APEXIII' _computing_data_collection 'Bruker APEXIII' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution SHELXS _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker PHOTON II' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0995 _diffrn_reflns_av_unetI/netI 0.0829 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 49715 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.999 _diffrn_reflns_theta_min 2.594 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.251 _exptl_crystal_description plate _exptl_crystal_F_000 1440 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM/EA/Pentane' _exptl_crystal_size_max 0.314 _exptl_crystal_size_mid 0.091 _exptl_crystal_size_min 0.036 _refine_diff_density_max 0.271 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 499 _refine_ls_number_reflns 7787 _refine_ls_number_restraints 144 _refine_ls_restrained_S_all 1.140 _refine_ls_R_factor_all 0.1420 _refine_ls_R_factor_gt 0.0892 _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^)+(0.0273P)^2^+5.1132P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1397 _refine_ls_wR_factor_ref 0.1553 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5150 _reflns_number_total 7787 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00225a2.cif _cod_data_source_block A19153O_014 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was changed to 'multi-scan' 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 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557383 _shelx_shelxl_version_number 2018/3 _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 0.973 _shelx_estimated_absorpt_t_max 0.997 _shelx_res_file ; TITL A19153O_014 in P2(1)/c A19153O_014.res created by SHELXL-2018/3 at 20:26:17 on 30-Oct-2019 CELL 0.71073 9.23140 19.63940 19.91210 90.0000 93.6052 90.0000 ZERR 8.00 0.00050 0.00110 0.00100 0.0000 0.0021 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 160 168 8 32 ACTA TEMP -120.3 SIZE 0.036 0.091 0.314 CONF MERG 2 L.S. 8 BOND $H FMAP 2 PLAN 10 ISOR 0.005 C15A > C18B SIMU 0.005 C15A > C18B OMIT -3 54.00 OMIT 8 5 13 OMIT 1 1 2 OMIT 8 17 6 OMIT -9 7 5 OMIT -1 1 2 OMIT 9 2 10 LIST 4 EQIV $1 x+1, y, z HTAB N13 O37_$1 EQIV $2 -x+1, -y+2, -z+1 HTAB N38 O12 WGHT 0.027300 5.113200 FVAR 0.14475 0.65589 C1 1 0.641297 0.581752 0.284462 11.00000 0.02375 0.02234 = 0.02330 -0.00824 -0.00354 0.00163 AFIX 43 H1 2 0.722483 0.604272 0.306110 11.00000 -1.20000 AFIX 0 C2 1 0.583679 0.525178 0.314008 11.00000 0.03189 0.02206 = 0.02659 -0.00433 -0.00156 0.00364 AFIX 43 H2 2 0.625437 0.508840 0.355762 11.00000 -1.20000 AFIX 0 C3 1 0.464955 0.492129 0.282875 11.00000 0.03239 0.01881 = 0.03443 -0.00510 0.00446 0.00239 AFIX 43 H3 2 0.424482 0.453564 0.303576 11.00000 -1.20000 AFIX 0 C4 1 0.405377 0.515433 0.221496 11.00000 0.02380 0.02609 = 0.04097 -0.01500 -0.00099 0.00217 AFIX 43 H4 2 0.324300 0.492718 0.199975 11.00000 -1.20000 AFIX 0 C5 1 0.463799 0.571536 0.191734 11.00000 0.02303 0.03133 = 0.02509 -0.00911 -0.00546 0.00400 AFIX 43 H5 2 0.423456 0.586813 0.149318 11.00000 -1.20000 AFIX 0 C6 1 0.581255 0.606208 0.222966 11.00000 0.02080 0.02833 = 0.01821 -0.00771 0.00075 0.00619 C7 1 0.635105 0.668983 0.190482 11.00000 0.02715 0.03481 = 0.01710 -0.00398 -0.00211 0.00317 O8 4 0.590122 0.684820 0.133862 11.00000 0.05452 0.06011 = 0.02121 0.00491 -0.01546 -0.01328 C9 1 0.745177 0.713782 0.229337 11.00000 0.01927 0.02887 = 0.01646 -0.00094 0.00075 0.00060 AFIX 13 H9 2 0.832807 0.685929 0.243004 11.00000 -1.20000 AFIX 0 C10 1 0.791298 0.774397 0.188243 11.00000 0.03397 0.04602 = 0.02107 0.00266 0.00888 -0.00498 AFIX 137 H10A 2 0.863837 0.801132 0.214863 11.00000 -1.50000 H10B 2 0.706552 0.802956 0.176219 11.00000 -1.50000 H10C 2 0.833234 0.758173 0.147161 11.00000 -1.50000 AFIX 0 C11 1 0.679435 0.740988 0.292229 11.00000 0.01281 0.01988 = 0.02017 0.00422 0.00024 -0.00111 O12 4 0.551995 0.759734 0.289630 11.00000 0.01125 0.04217 = 0.02359 0.00199 -0.00201 0.00609 N13 3 0.767889 0.745269 0.347063 11.00000 0.00985 0.02048 = 0.01677 0.00042 -0.00092 0.00343 H13 2 0.855942 0.736101 0.346865 11.00000 -1.20000 C14 1 0.730599 0.781520 0.407090 11.00000 0.01884 0.02150 = 0.01673 -0.00428 -0.00080 0.00375 AFIX 13 H14 2 0.623397 0.778568 0.411269 11.00000 -1.20000 AFIX 0 PART 1 21 C15A 1 0.774019 0.858075 0.397278 21.00000 0.02726 0.02066 = 0.02247 -0.00007 -0.00825 0.00330 O16A 4 0.831322 0.880995 0.351204 21.00000 0.03437 0.02238 = 0.04367 0.00946 -0.00243 -0.00252 O17A 4 0.753918 0.892438 0.452463 21.00000 0.03072 0.01999 = 0.02550 -0.00491 -0.00408 0.00224 C18A 1 0.796496 0.963353 0.450375 21.00000 0.05302 0.01441 = 0.03696 -0.00722 -0.00738 0.00322 AFIX 137 H18A 2 0.897052 0.966606 0.437582 21.00000 -1.50000 H18B 2 0.788646 0.983847 0.494872 21.00000 -1.50000 H18C 2 0.732597 0.987585 0.417257 21.00000 -1.50000 AFIX 0 PART 2 -21 C15B 1 0.751796 0.853404 0.402425 -21.00000 0.02823 0.02263 = 0.02480 0.00088 -0.00606 0.00177 O16B 4 0.784515 0.882081 0.349533 -21.00000 0.03538 0.02738 = 0.03888 0.00674 -0.00228 0.00155 O17B 4 0.702799 0.887342 0.457428 -21.00000 0.03172 0.02224 = 0.02958 -0.00485 -0.00244 0.00118 C18B 1 0.727592 0.960739 0.461279 -21.00000 0.04515 0.02456 = 0.04131 -0.00093 -0.00385 0.00554 AFIX 137 H18D 2 0.716425 0.976390 0.507399 -21.00000 -1.50000 H18E 2 0.656939 0.984103 0.430539 -21.00000 -1.50000 H18F 2 0.826045 0.970962 0.448481 -21.00000 -1.50000 AFIX 0 PART 0 C19 1 0.808895 0.750876 0.470159 11.00000 0.02643 0.01960 = 0.01758 -0.00079 -0.00502 0.00417 AFIX 23 H19A 2 0.914887 0.756033 0.466846 11.00000 -1.20000 H19B 2 0.781510 0.776938 0.509988 11.00000 -1.20000 AFIX 0 C20 1 0.774987 0.676535 0.480729 11.00000 0.02096 0.02428 = 0.01265 0.00146 -0.00624 -0.00168 C21 1 0.663087 0.658110 0.520476 11.00000 0.02084 0.03768 = 0.02170 0.00688 -0.00065 -0.00147 AFIX 43 H21 2 0.607636 0.692414 0.540612 11.00000 -1.20000 AFIX 0 C22 1 0.631764 0.590480 0.530969 11.00000 0.03298 0.05384 = 0.03212 0.01563 -0.00243 -0.01700 AFIX 43 H22 2 0.554538 0.578455 0.558023 11.00000 -1.20000 AFIX 0 C23 1 0.711735 0.540341 0.502475 11.00000 0.05378 0.02149 = 0.03872 0.01271 -0.01320 -0.01844 AFIX 43 H23 2 0.690289 0.493778 0.510130 11.00000 -1.20000 AFIX 0 C24 1 0.823843 0.557823 0.462510 11.00000 0.04504 0.02127 = 0.03101 -0.00032 -0.00869 -0.00143 AFIX 43 H24 2 0.879016 0.523332 0.442500 11.00000 -1.20000 AFIX 0 C25 1 0.854779 0.625746 0.451981 11.00000 0.02559 0.02009 = 0.01890 0.00192 -0.00265 -0.00164 AFIX 43 H25 2 0.931672 0.637710 0.424706 11.00000 -1.20000 AFIX 0 C26 1 -0.004560 0.562315 0.207282 11.00000 0.03558 0.01662 = 0.04857 0.00125 -0.00695 -0.00688 AFIX 43 H26 2 -0.034779 0.526567 0.235341 11.00000 -1.20000 AFIX 0 C27 1 -0.060877 0.566330 0.141998 11.00000 0.05281 0.02253 = 0.06344 -0.00480 -0.02751 -0.00912 AFIX 43 H27 2 -0.128398 0.533112 0.124971 11.00000 -1.20000 AFIX 0 C28 1 -0.019456 0.618648 0.101012 11.00000 0.05574 0.02862 = 0.03891 -0.00538 -0.02346 0.00541 AFIX 43 H28 2 -0.058838 0.621648 0.055870 11.00000 -1.20000 AFIX 0 C29 1 0.078830 0.666316 0.125715 11.00000 0.04832 0.02379 = 0.02790 -0.00010 -0.00609 -0.00183 AFIX 43 H29 2 0.107693 0.702306 0.097611 11.00000 -1.20000 AFIX 0 C30 1 0.135785 0.661965 0.191435 11.00000 0.02330 0.02075 = 0.02905 -0.00278 -0.00115 -0.00387 AFIX 43 H30 2 0.203192 0.695311 0.208293 11.00000 -1.20000 AFIX 0 C31 1 0.095865 0.609645 0.232997 11.00000 0.02053 0.01339 = 0.03210 -0.00497 0.00053 0.00159 C32 1 0.154175 0.601335 0.304040 11.00000 0.02877 0.01757 = 0.02968 0.00139 0.00579 -0.00132 O33 4 0.114829 0.555081 0.338503 11.00000 0.05681 0.02852 = 0.03915 0.01028 0.00668 -0.01865 C34 1 0.265093 0.652739 0.332567 11.00000 0.01852 0.01600 = 0.02107 0.00175 0.00421 0.00393 AFIX 13 H34 2 0.344232 0.657559 0.300834 11.00000 -1.20000 AFIX 0 C35 1 0.331467 0.632163 0.401841 11.00000 0.03346 0.02442 = 0.02372 0.00441 0.00014 0.01176 AFIX 137 H35A 2 0.399404 0.667481 0.418680 11.00000 -1.50000 H35B 2 0.383347 0.588910 0.398245 11.00000 -1.50000 H35C 2 0.254219 0.626904 0.433022 11.00000 -1.50000 AFIX 0 C36 1 0.190305 0.720868 0.339381 11.00000 0.01245 0.01941 = 0.01579 -0.00063 -0.00043 0.00318 O37 4 0.068080 0.723960 0.360904 11.00000 0.01309 0.02808 = 0.04243 0.00807 0.01038 0.00222 N38 3 0.264139 0.775814 0.323045 11.00000 0.01092 0.01795 = 0.01961 -0.00077 0.00344 0.00139 H38 2 0.349200 0.768633 0.313069 11.00000 -1.20000 C39 1 0.211438 0.843898 0.334115 11.00000 0.02111 0.01707 = 0.02077 -0.00083 -0.00310 0.00083 AFIX 13 H39 2 0.103623 0.844003 0.325175 11.00000 -1.20000 AFIX 0 C40 1 0.246196 0.868541 0.405497 11.00000 0.03107 0.01718 = 0.02560 0.00116 -0.00121 0.00316 O41 4 0.185091 0.915152 0.429946 11.00000 0.09184 0.04588 = 0.03617 -0.01875 -0.01517 0.03761 O42 4 0.353199 0.834515 0.437044 11.00000 0.03909 0.04793 = 0.01869 -0.00833 -0.00962 0.01795 C43 1 0.395245 0.856928 0.504811 11.00000 0.06298 0.07025 = 0.01927 -0.01269 -0.01365 0.01294 AFIX 137 H43A 2 0.468902 0.825968 0.525079 11.00000 -1.50000 H43B 2 0.310068 0.856876 0.531807 11.00000 -1.50000 H43C 2 0.435205 0.903098 0.503383 11.00000 -1.50000 AFIX 0 C44 1 0.277373 0.893088 0.284752 11.00000 0.03118 0.01755 = 0.02260 0.00042 -0.00191 -0.00349 AFIX 23 H44A 2 0.246753 0.940088 0.294922 11.00000 -1.20000 H44B 2 0.384511 0.891105 0.291150 11.00000 -1.20000 AFIX 0 C45 1 0.232293 0.876861 0.212016 11.00000 0.02386 0.01189 = 0.02332 0.00494 -0.00292 -0.00425 C46 1 0.324163 0.841430 0.172416 11.00000 0.01940 0.02796 = 0.03038 0.00476 -0.00126 0.00018 AFIX 43 H46 2 0.415632 0.826062 0.191061 11.00000 -1.20000 AFIX 0 C47 1 0.283085 0.828294 0.105594 11.00000 0.02951 0.03611 = 0.02676 -0.00370 0.00641 -0.00561 AFIX 43 H47 2 0.346871 0.804097 0.078546 11.00000 -1.20000 AFIX 0 C48 1 0.150061 0.850095 0.077928 11.00000 0.03544 0.03595 = 0.01922 0.00515 -0.00127 -0.01020 AFIX 43 H48 2 0.123189 0.841420 0.031885 11.00000 -1.20000 AFIX 0 C49 1 0.056989 0.884236 0.116996 11.00000 0.02620 0.02905 = 0.02828 0.00834 -0.00669 0.00014 AFIX 43 H49 2 -0.035141 0.898728 0.098349 11.00000 -1.20000 AFIX 0 C50 1 0.097962 0.897519 0.183867 11.00000 0.02743 0.01982 = 0.02802 -0.00052 0.00175 -0.00146 AFIX 43 H50 2 0.033154 0.921124 0.210874 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM A19153O_014 in P2(1)/c REM wR2 = 0.1553, GooF = S = 1.144, Restrained GooF = 1.140 for all data REM R1 = 0.0892 for 5150 Fo > 4sig(Fo) and 0.1420 for all 7787 data REM 499 parameters refined using 144 restraints END WGHT 0.0273 5.1135 REM Highest difference peak 0.271, deepest hole -0.308, 1-sigma level 0.059 Q1 1 0.1344 0.8558 0.2115 11.00000 0.05 0.27 Q2 1 0.6107 0.6430 0.2153 11.00000 0.05 0.26 Q3 1 0.8920 0.9604 0.4647 11.00000 0.05 0.24 Q4 1 0.7808 0.7549 0.4309 11.00000 0.05 0.24 Q5 1 0.2821 0.9207 0.4220 11.00000 0.05 0.24 Q6 1 0.3401 0.7628 0.0316 11.00000 0.05 0.24 Q7 1 0.1869 0.5754 0.1379 11.00000 0.05 0.23 Q8 1 0.5833 0.6059 0.2556 11.00000 0.05 0.22 Q9 1 0.3868 0.7167 0.3065 11.00000 0.05 0.22 Q10 1 0.3992 0.5815 0.3180 11.00000 0.05 0.22 ; _shelx_res_checksum 14712 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 C1 C 0.6413(3) 0.58175(15) 0.28446(15) 0.0233(7) Uani 1 1 d . . . . . H1 H 0.722483 0.604272 0.306110 0.028 Uiso 1 1 calc R U . . . C2 C 0.5837(4) 0.52518(16) 0.31401(16) 0.0270(7) Uani 1 1 d . . . . . H2 H 0.625437 0.508840 0.355762 0.032 Uiso 1 1 calc R U . . . C3 C 0.4650(4) 0.49213(16) 0.28288(17) 0.0284(8) Uani 1 1 d . . . . . H3 H 0.424482 0.453564 0.303576 0.034 Uiso 1 1 calc R U . . . C4 C 0.4054(4) 0.51543(17) 0.22150(17) 0.0304(8) Uani 1 1 d . . . . . H4 H 0.324300 0.492718 0.199975 0.036 Uiso 1 1 calc R U . . . C5 C 0.4638(3) 0.57154(16) 0.19173(16) 0.0268(7) Uani 1 1 d . . . . . H5 H 0.423456 0.586813 0.149318 0.032 Uiso 1 1 calc R U . . . C6 C 0.5813(3) 0.60621(16) 0.22297(15) 0.0225(7) Uani 1 1 d . . . . . C7 C 0.6351(4) 0.66898(17) 0.19048(15) 0.0265(7) Uani 1 1 d . . . . . O8 O 0.5901(3) 0.68482(14) 0.13386(11) 0.0460(7) Uani 1 1 d . . . . . C9 C 0.7452(3) 0.71378(16) 0.22934(14) 0.0215(7) Uani 1 1 d . . . . . H9 H 0.832807 0.685929 0.243004 0.026 Uiso 1 1 calc R U . . . C10 C 0.7913(4) 0.77440(18) 0.18824(16) 0.0334(8) Uani 1 1 d . . . . . H10A H 0.863837 0.801132 0.214863 0.050 Uiso 1 1 calc R U . . . H10B H 0.706552 0.802956 0.176219 0.050 Uiso 1 1 calc R U . . . H10C H 0.833234 0.758173 0.147161 0.050 Uiso 1 1 calc R U . . . C11 C 0.6794(3) 0.74099(15) 0.29223(14) 0.0177(6) Uani 1 1 d . . . . . O12 O 0.5520(2) 0.75973(11) 0.28963(10) 0.0258(5) Uani 1 1 d . . . . . N13 N 0.7679(3) 0.74527(12) 0.34706(12) 0.0158(5) Uani 1 1 d . . . . . H13 H 0.856(3) 0.7361(15) 0.3469(15) 0.019 Uiso 1 1 d . U . . . C14 C 0.7306(3) 0.78152(15) 0.40709(14) 0.0191(6) Uani 1 1 d . . . . . H14 H 0.623397 0.778568 0.411269 0.023 Uiso 1 1 calc R U . A 1 C15A C 0.7740(13) 0.8581(7) 0.3973(7) 0.0239(14) Uani 0.656(16) 1 d . U P B 1 O16A O 0.8313(9) 0.8810(5) 0.3512(5) 0.0337(15) Uani 0.656(16) 1 d . U P B 1 O17A O 0.7539(9) 0.8924(3) 0.4525(3) 0.0257(11) Uani 0.656(16) 1 d . U P B 1 C18A C 0.7965(12) 0.9634(3) 0.4504(4) 0.0352(18) Uani 0.656(16) 1 d . U P B 1 H18A H 0.897052 0.966606 0.437582 0.053 Uiso 0.656(16) 1 calc R U P B 1 H18B H 0.788646 0.983847 0.494872 0.053 Uiso 0.656(16) 1 calc R U P B 1 H18C H 0.732597 0.987585 0.417257 0.053 Uiso 0.656(16) 1 calc R U P B 1 C15B C 0.752(3) 0.8534(15) 0.4024(14) 0.0255(17) Uani 0.344(16) 1 d . U P B 2 O16B O 0.7845(17) 0.8821(11) 0.3495(11) 0.034(3) Uani 0.344(16) 1 d . U P B 2 O17B O 0.7028(15) 0.8873(6) 0.4574(6) 0.0280(15) Uani 0.344(16) 1 d . U P B 2 C18B C 0.728(2) 0.9607(7) 0.4613(8) 0.037(3) Uani 0.344(16) 1 d . U P B 2 H18D H 0.716425 0.976390 0.507399 0.056 Uiso 0.344(16) 1 calc R U P B 2 H18E H 0.656939 0.984103 0.430539 0.056 Uiso 0.344(16) 1 calc R U P B 2 H18F H 0.826045 0.970962 0.448481 0.056 Uiso 0.344(16) 1 calc R U P B 2 C19 C 0.8089(3) 0.75088(15) 0.47016(14) 0.0215(7) Uani 1 1 d . . . . . H19A H 0.914887 0.756033 0.466846 0.026 Uiso 1 1 calc R U . . . H19B H 0.781510 0.776938 0.509988 0.026 Uiso 1 1 calc R U . . . C20 C 0.7750(3) 0.67654(15) 0.48073(14) 0.0196(7) Uani 1 1 d . . . . . C21 C 0.6631(3) 0.65811(18) 0.52048(15) 0.0268(7) Uani 1 1 d . . . . . H21 H 0.607636 0.692414 0.540612 0.032 Uiso 1 1 calc R U . . . C22 C 0.6318(4) 0.5905(2) 0.53097(18) 0.0398(9) Uani 1 1 d . . . . . H22 H 0.554538 0.578455 0.558023 0.048 Uiso 1 1 calc R U . . . C23 C 0.7117(4) 0.54034(18) 0.50248(18) 0.0387(9) Uani 1 1 d . . . . . H23 H 0.690289 0.493778 0.510130 0.046 Uiso 1 1 calc R U . . . C24 C 0.8238(4) 0.55782(16) 0.46251(17) 0.0329(8) Uani 1 1 d . . . . . H24 H 0.879016 0.523332 0.442500 0.039 Uiso 1 1 calc R U . . . C25 C 0.8548(3) 0.62575(15) 0.45198(15) 0.0217(7) Uani 1 1 d . . . . . H25 H 0.931672 0.637710 0.424706 0.026 Uiso 1 1 calc R U . . . C26 C -0.0046(4) 0.56232(16) 0.20728(18) 0.0340(9) Uani 1 1 d . . . . . H26 H -0.034779 0.526567 0.235341 0.041 Uiso 1 1 calc R U . . . C27 C -0.0609(4) 0.56633(18) 0.1420(2) 0.0476(11) Uani 1 1 d . . . . . H27 H -0.128398 0.533112 0.124971 0.057 Uiso 1 1 calc R U . . . C28 C -0.0195(4) 0.61865(18) 0.10101(19) 0.0422(10) Uani 1 1 d . . . . . H28 H -0.058838 0.621648 0.055870 0.051 Uiso 1 1 calc R U . . . C29 C 0.0788(4) 0.66632(17) 0.12572(17) 0.0337(8) Uani 1 1 d . . . . . H29 H 0.107693 0.702306 0.097611 0.040 Uiso 1 1 calc R U . . . C30 C 0.1358(3) 0.66196(16) 0.19144(16) 0.0245(7) Uani 1 1 d . . . . . H30 H 0.203192 0.695311 0.208293 0.029 Uiso 1 1 calc R U . . . C31 C 0.0959(3) 0.60965(14) 0.23300(16) 0.0221(7) Uani 1 1 d . . . . . C32 C 0.1542(4) 0.60134(15) 0.30404(16) 0.0252(7) Uani 1 1 d . . . . . O33 O 0.1148(3) 0.55508(12) 0.33850(12) 0.0413(7) Uani 1 1 d . . . . . C34 C 0.2651(3) 0.65274(14) 0.33257(14) 0.0184(6) Uani 1 1 d . . . . . H34 H 0.344232 0.657559 0.300834 0.022 Uiso 1 1 calc R U . . . C35 C 0.3315(4) 0.63216(16) 0.40184(15) 0.0273(8) Uani 1 1 d . . . . . H35A H 0.399404 0.667481 0.418680 0.041 Uiso 1 1 calc R U . . . H35B H 0.383347 0.588910 0.398245 0.041 Uiso 1 1 calc R U . . . H35C H 0.254219 0.626904 0.433022 0.041 Uiso 1 1 calc R U . . . C36 C 0.1903(3) 0.72087(14) 0.33938(14) 0.0159(6) Uani 1 1 d . . . . . O37 O 0.0681(2) 0.72396(11) 0.36090(11) 0.0275(5) Uani 1 1 d . . . . . N38 N 0.2641(3) 0.77581(12) 0.32305(12) 0.0161(5) Uani 1 1 d . . . . . H38 H 0.349(3) 0.7686(15) 0.3131(15) 0.019 Uiso 1 1 d . U . . . C39 C 0.2114(3) 0.84390(14) 0.33412(14) 0.0198(7) Uani 1 1 d . . . . . H39 H 0.103623 0.844003 0.325175 0.024 Uiso 1 1 calc R U . . . C40 C 0.2462(4) 0.86854(15) 0.40550(16) 0.0247(7) Uani 1 1 d . . . . . O41 O 0.1851(3) 0.91515(14) 0.42995(13) 0.0588(9) Uani 1 1 d . . . . . O42 O 0.3532(3) 0.83452(12) 0.43704(11) 0.0357(6) Uani 1 1 d . . . . . C43 C 0.3952(5) 0.8569(2) 0.50481(17) 0.0515(11) Uani 1 1 d . . . . . H43A H 0.468902 0.825968 0.525079 0.077 Uiso 1 1 calc R U . . . H43B H 0.310068 0.856876 0.531807 0.077 Uiso 1 1 calc R U . . . H43C H 0.435205 0.903098 0.503383 0.077 Uiso 1 1 calc R U . . . C44 C 0.2774(4) 0.89309(15) 0.28475(14) 0.0239(7) Uani 1 1 d . . . . . H44A H 0.246753 0.940088 0.294922 0.029 Uiso 1 1 calc R U . . . H44B H 0.384511 0.891105 0.291150 0.029 Uiso 1 1 calc R U . . . C45 C 0.2323(3) 0.87686(14) 0.21202(15) 0.0199(7) Uani 1 1 d . . . . . C46 C 0.3242(3) 0.84143(16) 0.17242(16) 0.0260(7) Uani 1 1 d . . . . . H46 H 0.415632 0.826062 0.191061 0.031 Uiso 1 1 calc R U . . . C47 C 0.2831(4) 0.82829(17) 0.10559(16) 0.0306(8) Uani 1 1 d . . . . . H47 H 0.346871 0.804097 0.078546 0.037 Uiso 1 1 calc R U . . . C48 C 0.1501(4) 0.85009(17) 0.07793(16) 0.0303(8) Uani 1 1 d . . . . . H48 H 0.123189 0.841420 0.031885 0.036 Uiso 1 1 calc R U . . . C49 C 0.0570(4) 0.88424(16) 0.11700(16) 0.0282(8) Uani 1 1 d . . . . . H49 H -0.035141 0.898728 0.098349 0.034 Uiso 1 1 calc R U . . . C50 C 0.0980(3) 0.89752(15) 0.18387(16) 0.0251(7) Uani 1 1 d . . . . . H50 H 0.033154 0.921124 0.210874 0.030 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 C1 0.0237(17) 0.0223(16) 0.0233(17) -0.0082(13) -0.0035(14) 0.0016(14) C2 0.0319(19) 0.0221(17) 0.0266(18) -0.0043(14) -0.0016(15) 0.0036(15) C3 0.0324(19) 0.0188(16) 0.0344(19) -0.0051(14) 0.0045(16) 0.0024(15) C4 0.0238(18) 0.0261(18) 0.041(2) -0.0150(15) -0.0010(16) 0.0022(15) C5 0.0230(17) 0.0313(18) 0.0251(17) -0.0091(14) -0.0055(14) 0.0040(15) C6 0.0208(16) 0.0283(17) 0.0182(15) -0.0077(13) 0.0008(13) 0.0062(14) C7 0.0272(18) 0.0348(19) 0.0171(16) -0.0040(14) -0.0021(14) 0.0032(15) O8 0.0545(18) 0.0601(18) 0.0212(13) 0.0049(12) -0.0155(12) -0.0133(14) C9 0.0193(16) 0.0289(17) 0.0165(15) -0.0009(13) 0.0007(13) 0.0006(14) C10 0.034(2) 0.046(2) 0.0211(17) 0.0027(15) 0.0089(15) -0.0050(17) C11 0.0128(15) 0.0199(15) 0.0202(15) 0.0042(12) 0.0002(12) -0.0011(12) O12 0.0113(11) 0.0422(14) 0.0236(11) 0.0020(10) -0.0020(9) 0.0061(10) N13 0.0099(12) 0.0205(13) 0.0168(12) 0.0004(10) -0.0009(11) 0.0034(11) C14 0.0188(16) 0.0215(15) 0.0167(15) -0.0043(12) -0.0008(12) 0.0037(13) C15A 0.027(3) 0.021(2) 0.022(2) -0.0001(19) -0.008(2) 0.003(2) O16A 0.034(4) 0.022(2) 0.044(2) 0.0095(18) -0.002(3) -0.003(3) O17A 0.031(3) 0.0200(16) 0.0255(16) -0.0049(13) -0.004(2) 0.002(2) C18A 0.053(4) 0.014(2) 0.037(3) -0.007(2) -0.007(3) 0.003(3) C15B 0.028(3) 0.023(3) 0.025(3) 0.001(2) -0.006(3) 0.002(3) O16B 0.035(5) 0.027(4) 0.039(4) 0.007(3) -0.002(5) 0.002(5) O17B 0.032(3) 0.022(2) 0.030(2) -0.005(2) -0.002(3) 0.001(3) C18B 0.045(5) 0.025(4) 0.041(4) -0.001(4) -0.004(4) 0.006(5) C19 0.0264(17) 0.0196(15) 0.0176(15) -0.0008(12) -0.0050(13) 0.0042(13) C20 0.0210(16) 0.0243(16) 0.0126(14) 0.0015(12) -0.0062(13) -0.0017(13) C21 0.0208(17) 0.0377(19) 0.0217(17) 0.0069(14) -0.0007(14) -0.0015(15) C22 0.033(2) 0.054(3) 0.032(2) 0.0156(18) -0.0024(17) -0.0170(19) C23 0.054(3) 0.0215(18) 0.039(2) 0.0127(16) -0.0132(19) -0.0184(18) C24 0.045(2) 0.0213(17) 0.0310(19) -0.0003(14) -0.0087(17) -0.0014(16) C25 0.0256(18) 0.0201(15) 0.0189(16) 0.0019(12) -0.0027(13) -0.0016(13) C26 0.036(2) 0.0166(16) 0.049(2) 0.0012(15) -0.0070(18) -0.0069(15) C27 0.053(3) 0.0225(19) 0.063(3) -0.0048(18) -0.028(2) -0.0091(18) C28 0.056(3) 0.029(2) 0.039(2) -0.0054(17) -0.0235(19) 0.0054(18) C29 0.048(2) 0.0238(18) 0.0279(18) -0.0001(14) -0.0061(17) -0.0018(17) C30 0.0233(17) 0.0208(16) 0.0291(17) -0.0028(13) -0.0012(14) -0.0039(14) C31 0.0205(17) 0.0134(14) 0.0321(18) -0.0050(13) 0.0005(14) 0.0016(13) C32 0.0288(18) 0.0176(16) 0.0297(18) 0.0014(13) 0.0058(15) -0.0013(14) O33 0.0568(17) 0.0285(13) 0.0392(15) 0.0103(11) 0.0067(13) -0.0187(13) C34 0.0185(16) 0.0160(14) 0.0211(16) 0.0017(12) 0.0042(13) 0.0039(13) C35 0.0335(19) 0.0244(17) 0.0237(17) 0.0044(13) 0.0001(15) 0.0118(15) C36 0.0125(15) 0.0194(15) 0.0158(14) -0.0006(12) -0.0004(12) 0.0032(12) O37 0.0131(11) 0.0281(12) 0.0424(14) 0.0081(10) 0.0104(10) 0.0022(10) N38 0.0109(12) 0.0180(13) 0.0196(13) -0.0008(10) 0.0034(10) 0.0014(11) C39 0.0211(16) 0.0171(15) 0.0208(16) -0.0008(12) -0.0031(13) 0.0008(13) C40 0.0311(19) 0.0172(15) 0.0256(17) 0.0012(13) -0.0012(15) 0.0032(14) O41 0.092(2) 0.0459(17) 0.0362(15) -0.0188(13) -0.0152(15) 0.0376(17) O42 0.0391(15) 0.0479(15) 0.0187(12) -0.0083(11) -0.0096(10) 0.0180(12) C43 0.063(3) 0.070(3) 0.0193(18) -0.0127(18) -0.0137(19) 0.013(2) C44 0.0312(19) 0.0175(15) 0.0226(16) 0.0004(13) -0.0019(14) -0.0035(14) C45 0.0239(17) 0.0119(14) 0.0233(16) 0.0049(12) -0.0029(13) -0.0042(13) C46 0.0194(17) 0.0280(17) 0.0304(18) 0.0048(14) -0.0013(14) 0.0002(14) C47 0.030(2) 0.036(2) 0.0268(18) -0.0037(15) 0.0064(15) -0.0056(16) C48 0.035(2) 0.036(2) 0.0192(17) 0.0052(14) -0.0013(15) -0.0102(17) C49 0.0262(18) 0.0291(18) 0.0283(18) 0.0083(14) -0.0067(15) 0.0001(15) C50 0.0274(18) 0.0198(16) 0.0280(18) -0.0005(13) 0.0017(14) -0.0015(14) 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' N N 0.0061 0.0033 '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' 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 C2 C1 C6 120.6(3) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 118.5(3) . . ? C5 C6 C7 118.8(3) . . ? C1 C6 C7 122.6(3) . . ? O8 C7 C6 120.6(3) . . ? O8 C7 C9 120.1(3) . . ? C6 C7 C9 119.2(3) . . ? C7 C9 C10 112.4(3) . . ? C7 C9 C11 109.5(2) . . ? C10 C9 C11 107.9(3) . . ? C7 C9 H9 109.0 . . ? C10 C9 H9 109.0 . . ? C11 C9 H9 109.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O12 C11 N13 123.6(3) . . ? O12 C11 C9 120.0(3) . . ? N13 C11 C9 116.3(3) . . ? C11 N13 C14 123.0(2) . . ? C11 N13 H13 122(2) . . ? C14 N13 H13 113(2) . . ? C15B C14 N13 113.0(11) . . ? C15B C14 C19 112.4(11) . . ? N13 C14 C19 111.0(2) . . ? N13 C14 C15A 106.9(5) . . ? C19 C14 C15A 111.5(5) . . ? N13 C14 H14 109.1 . . ? C19 C14 H14 109.1 . . ? C15A C14 H14 109.1 . . ? O16A C15A O17A 123.4(11) . . ? O16A C15A C14 126.4(12) . . ? O17A C15A C14 109.7(8) . . ? C15A O17A C18A 114.7(6) . . ? O17A C18A H18A 109.5 . . ? O17A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? O17A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? O16B C15B O17B 124(2) . . ? O16B C15B C14 123(2) . . ? O17B C15B C14 111.8(16) . . ? C15B O17B C18B 117.3(13) . . ? O17B C18B H18D 109.5 . . ? O17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? O17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C20 C19 C14 113.7(2) . . ? C20 C19 H19A 108.8 . . ? C14 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C14 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C25 C20 C21 118.8(3) . . ? C25 C20 C19 121.2(3) . . ? C21 C20 C19 120.0(3) . . ? C22 C21 C20 120.6(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.9(3) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 119.6(3) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C20 120.8(3) . . ? C24 C25 H25 119.6 . . ? C20 C25 H25 119.6 . . ? C27 C26 C31 121.0(3) . . ? C27 C26 H26 119.5 . . ? C31 C26 H26 119.5 . . ? C26 C27 C28 120.0(3) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 120.0(3) . . ? C28 C29 H29 120.0 . . ? C30 C29 H29 120.0 . . ? C29 C30 C31 120.8(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C30 C31 C26 118.3(3) . . ? C30 C31 C32 123.7(3) . . ? C26 C31 C32 118.0(3) . . ? O33 C32 C31 121.2(3) . . ? O33 C32 C34 120.4(3) . . ? C31 C32 C34 118.4(3) . . ? C36 C34 C32 108.6(2) . . ? C36 C34 C35 108.2(2) . . ? C32 C34 C35 112.6(3) . . ? C36 C34 H34 109.1 . . ? C32 C34 H34 109.1 . . ? C35 C34 H34 109.1 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O37 C36 N38 122.7(3) . . ? O37 C36 C34 120.4(3) . . ? N38 C36 C34 116.9(2) . . ? C36 N38 C39 122.1(2) . . ? C36 N38 H38 115(2) . . ? C39 N38 H38 122(2) . . ? N38 C39 C40 112.6(2) . . ? N38 C39 C44 109.6(2) . . ? C40 C39 C44 109.3(2) . . ? N38 C39 H39 108.4 . . ? C40 C39 H39 108.4 . . ? C44 C39 H39 108.4 . . ? O41 C40 O42 123.6(3) . . ? O41 C40 C39 123.3(3) . . ? O42 C40 C39 113.1(3) . . ? C40 O42 C43 116.0(3) . . ? O42 C43 H43A 109.5 . . ? O42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C45 C44 C39 112.6(2) . . ? C45 C44 H44A 109.1 . . ? C39 C44 H44A 109.1 . . ? C45 C44 H44B 109.1 . . ? C39 C44 H44B 109.1 . . ? H44A C44 H44B 107.8 . . ? C46 C45 C50 118.8(3) . . ? C46 C45 C44 120.6(3) . . ? C50 C45 C44 120.6(3) . . ? C45 C46 C47 120.1(3) . . ? C45 C46 H46 120.0 . . ? C47 C46 H46 120.0 . . ? C48 C47 C46 120.5(3) . . ? C48 C47 H47 119.7 . . ? C46 C47 H47 119.7 . . ? C49 C48 C47 119.9(3) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C50 119.6(3) . . ? C48 C49 H49 120.2 . . ? C50 C49 H49 120.2 . . ? C49 C50 C45 121.0(3) . . ? C49 C50 H50 119.5 . . ? C45 C50 H50 119.5 . . ? 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 C1 C2 1.379(4) . ? C1 C6 1.397(4) . ? C1 H1 0.9500 . ? C2 C3 1.386(4) . ? C2 H2 0.9500 . ? C3 C4 1.386(5) . ? C3 H3 0.9500 . ? C4 C5 1.377(5) . ? C4 H4 0.9500 . ? C5 C6 1.393(4) . ? C5 H5 0.9500 . ? C6 C7 1.492(4) . ? C7 O8 1.217(4) . ? C7 C9 1.519(4) . ? C9 C10 1.520(4) . ? C9 C11 1.522(4) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O12 1.231(3) . ? C11 N13 1.324(4) . ? N13 C14 1.451(4) . ? N13 H13 0.83(3) . ? C14 C15B 1.43(3) . ? C14 C19 1.532(4) . ? C14 C15A 1.571(14) . ? C14 H14 1.0000 . ? C15A O16A 1.177(15) . ? C15A O17A 1.313(14) . ? O17A C18A 1.448(8) . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C15B O16B 1.25(3) . ? C15B O17B 1.38(3) . ? O17B C18B 1.461(17) . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 0.9800 . ? C19 C20 1.511(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C25 1.385(4) . ? C20 C21 1.388(4) . ? C21 C22 1.378(5) . ? C21 H21 0.9500 . ? C22 C23 1.374(5) . ? C22 H22 0.9500 . ? C23 C24 1.388(5) . ? C23 H23 0.9500 . ? C24 C25 1.383(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.372(5) . ? C26 C31 1.388(4) . ? C26 H26 0.9500 . ? C27 C28 1.381(5) . ? C27 H27 0.9500 . ? C28 C29 1.373(5) . ? C28 H28 0.9500 . ? C29 C30 1.382(4) . ? C29 H29 0.9500 . ? C30 C31 1.384(4) . ? C30 H30 0.9500 . ? C31 C32 1.491(4) . ? C32 O33 1.208(4) . ? C32 C34 1.522(4) . ? C34 C36 1.516(4) . ? C34 C35 1.528(4) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 O37 1.233(3) . ? C36 N38 1.328(4) . ? N38 C39 1.445(4) . ? N38 H38 0.83(3) . ? C39 C40 1.517(4) . ? C39 C44 1.531(4) . ? C39 H39 1.0000 . ? C40 O41 1.195(4) . ? C40 O42 1.319(4) . ? O42 C43 1.449(4) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.515(4) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.382(4) . ? C45 C50 1.389(4) . ? C46 C47 1.385(4) . ? C46 H46 0.9500 . ? C47 C48 1.382(5) . ? C47 H47 0.9500 . ? C48 C49 1.370(5) . ? C48 H48 0.9500 . ? C49 C50 1.386(4) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? 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 _geom_hbond_publ_flag N13 H13 O37 0.83(3) 1.98(3) 2.799(3) 170(3) 1_655 yes N38 H38 O12 0.83(3) 1.97(3) 2.798(3) 175(3) . yes 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 C6 C1 C2 C3 -0.2(5) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? C4 C5 C6 C1 1.7(5) . . . . ? C4 C5 C6 C7 -176.6(3) . . . . ? C2 C1 C6 C5 -1.1(4) . . . . ? C2 C1 C6 C7 177.1(3) . . . . ? C5 C6 C7 O8 -9.3(5) . . . . ? C1 C6 C7 O8 172.5(3) . . . . ? C5 C6 C7 C9 169.6(3) . . . . ? C1 C6 C7 C9 -8.5(4) . . . . ? O8 C7 C9 C10 -2.6(4) . . . . ? C6 C7 C9 C10 178.5(3) . . . . ? O8 C7 C9 C11 117.3(3) . . . . ? C6 C7 C9 C11 -61.7(4) . . . . ? C7 C9 C11 O12 -40.3(4) . . . . ? C10 C9 C11 O12 82.2(3) . . . . ? C7 C9 C11 N13 142.1(3) . . . . ? C10 C9 C11 N13 -95.3(3) . . . . ? O12 C11 N13 C14 -9.3(5) . . . . ? C9 C11 N13 C14 168.1(3) . . . . ? C11 N13 C14 C15B -80.8(11) . . . . ? C11 N13 C14 C19 151.8(3) . . . . ? C11 N13 C14 C15A -86.3(6) . . . . ? N13 C14 C15A O16A -2.8(13) . . . . ? C19 C14 C15A O16A 118.7(11) . . . . ? N13 C14 C15A O17A -174.8(6) . . . . ? C19 C14 C15A O17A -53.3(8) . . . . ? O16A C15A O17A C18A 5.2(14) . . . . ? C14 C15A O17A C18A 177.4(6) . . . . ? N13 C14 C15B O16B 7(2) . . . . ? C19 C14 C15B O16B 133.6(19) . . . . ? N13 C14 C15B O17B 174.3(12) . . . . ? C19 C14 C15B O17B -59.1(17) . . . . ? O16B C15B O17B C18B -17(3) . . . . ? C14 C15B O17B C18B 175.7(13) . . . . ? C15B C14 C19 C20 173.4(11) . . . . ? N13 C14 C19 C20 -58.9(3) . . . . ? C15A C14 C19 C20 -178.0(5) . . . . ? C14 C19 C20 C25 87.9(3) . . . . ? C14 C19 C20 C21 -92.8(3) . . . . ? C25 C20 C21 C22 -0.2(4) . . . . ? C19 C20 C21 C22 -179.5(3) . . . . ? C20 C21 C22 C23 0.4(5) . . . . ? C21 C22 C23 C24 -0.5(5) . . . . ? C22 C23 C24 C25 0.4(5) . . . . ? C23 C24 C25 C20 -0.1(5) . . . . ? C21 C20 C25 C24 0.0(4) . . . . ? C19 C20 C25 C24 179.3(3) . . . . ? C31 C26 C27 C28 -1.0(6) . . . . ? C26 C27 C28 C29 0.4(6) . . . . ? C27 C28 C29 C30 -0.1(6) . . . . ? C28 C29 C30 C31 0.5(5) . . . . ? C29 C30 C31 C26 -1.0(5) . . . . ? C29 C30 C31 C32 179.3(3) . . . . ? C27 C26 C31 C30 1.3(5) . . . . ? C27 C26 C31 C32 -179.0(3) . . . . ? C30 C31 C32 O33 179.3(3) . . . . ? C26 C31 C32 O33 -0.4(5) . . . . ? C30 C31 C32 C34 -0.6(4) . . . . ? C26 C31 C32 C34 179.6(3) . . . . ? O33 C32 C34 C36 -111.3(3) . . . . ? C31 C32 C34 C36 68.7(3) . . . . ? O33 C32 C34 C35 8.5(4) . . . . ? C31 C32 C34 C35 -171.6(3) . . . . ? C32 C34 C36 O37 41.9(4) . . . . ? C35 C34 C36 O37 -80.5(3) . . . . ? C32 C34 C36 N38 -139.9(3) . . . . ? C35 C34 C36 N38 97.6(3) . . . . ? O37 C36 N38 C39 4.9(4) . . . . ? C34 C36 N38 C39 -173.2(2) . . . . ? C36 N38 C39 C40 83.1(3) . . . . ? C36 N38 C39 C44 -154.9(3) . . . . ? N38 C39 C40 O41 -161.6(3) . . . . ? C44 C39 C40 O41 76.3(4) . . . . ? N38 C39 C40 O42 20.1(4) . . . . ? C44 C39 C40 O42 -101.9(3) . . . . ? O41 C40 O42 C43 -0.2(5) . . . . ? C39 C40 O42 C43 178.1(3) . . . . ? N38 C39 C44 C45 63.0(3) . . . . ? C40 C39 C44 C45 -173.1(3) . . . . ? C39 C44 C45 C46 -99.8(3) . . . . ? C39 C44 C45 C50 80.4(3) . . . . ? C50 C45 C46 C47 1.3(4) . . . . ? C44 C45 C46 C47 -178.5(3) . . . . ? C45 C46 C47 C48 -0.3(5) . . . . ? C46 C47 C48 C49 -0.8(5) . . . . ? C47 C48 C49 C50 0.9(5) . . . . ? C48 C49 C50 C45 0.1(5) . . . . ? C46 C45 C50 C49 -1.2(4) . . . . ? C44 C45 C50 C49 178.6(3) . . . . ?