#------------------------------------------------------------------------------ #$Date: 2024-08-05 21:12:58 +0300 (Mon, 05 Aug 2024) $ #$Revision: 293778 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572027.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_1572027 loop_ _publ_author_name 'Nascimento, Mitchell A.' 'LaPierre, Etienne A.' 'Patrick, Brian O.' 'Watson, Jade E. T.' 'Watanabe, Lara' 'Rawson, Jeremy' 'Hering-Junghans, Christian' 'Manners, Ian' _publ_section_title ; 1,3-Dipolar cyclisation reactions of nitriles with sterically encumbered cyclic triphosphanes: synthesis and electronic structure of phosphorus-rich heterocycles with tunable colour. ; _journal_issue 30 _journal_name_full 'Chemical science' _journal_page_first 12006 _journal_page_last 12016 _journal_paper_doi 10.1039/d4sc02497d _journal_volume 15 _journal_year 2024 _chemical_formula_moiety 'C38 H55 N P3, C F3 O3 S, C6 H5 F' _chemical_formula_sum 'C45 H60 F4 N O3 P3 S' _chemical_formula_weight 863.91 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2022-05-23 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2023-09-05 deposited with the CCDC. 2024-07-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.752(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.6808(4) _cell_length_b 20.4088(8) _cell_length_c 20.8267(8) _cell_measurement_reflns_used 9933 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.51 _cell_measurement_theta_min 2.28 _cell_volume 4508.4(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_unetI/netI 0.0341 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 60974 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.587 _diffrn_reflns_theta_min 1.402 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_T_max .7461 _exptl_absorpt_correction_T_min .7011 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_crystal_colour Red _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1832 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.658 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 534 _refine_ls_number_reflns 13812 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0408 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+1.8958P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1094 _reflns_Friedel_coverage 0.000 _reflns_number_gt 10809 _reflns_number_total 13812 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02497d4.cif _cod_data_source_block im047_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_refine_ls_hydrogen_treatment' value 'Mixed' was changed to 'mixed' 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 Adding full bibliography for 1572027--1572043.cif. ; _cod_database_code 1572027 _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_max 0.955 _shelx_estimated_absorpt_t_min 0.923 _olex2_refinement_description ; 1. Shared sites {F4A, H40} {F4C, H42} {F4B, H43} 2. Uiso/Uaniso restraints and constraints Uiso(F4A) = Uiso(H40) Uiso(F4C) = Uiso(H42) Uiso(F4B) = Uiso(H43) 3. Others Fixed Sof: F4B(0.4) F4A(0.3) F4C(0.3) H40(0.7) H42(0.7) H43(0.6) 4.a Ternary CH refined with riding coordinates: C9(H9), C36(H36), C12(H12), C24(H24), C21(H21), C33(H33) 4.b Aromatic/amide H refined with riding coordinates: C7(H7), C19(H19), C6(H6), C5(H5), C29(H29), C18(H18), C17(H17), C30(H30), C31(H31), C45(H45), C41(H41), C44(H44) 4.c Idealised Me refined as rotating group: C37(H37A,H37B,H37C), C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B, H11C), C13(H13A,H13B,H13C), C38(H38A,H38B,H38C), C14(H14A,H14B,H14C), C22(H22A, H22B,H22C), C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C35(H35A,H35B,H35C), C34(H34A,H34B,H34C) ; _shelx_res_file ; TITL im047_a.res in P2(1)/n im047_a.res created by SHELXL-2018/3 at 18:04:52 on 09-Dec-2020 REM Old TITL im047 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.145, Rweak 0.006, Alpha 0.036 REM 0.552 for 285 systematic absences, Orientation as input REM Formula found by SHELXT: C41 F4A F2 S1 CELL 0.71073 10.6808 20.4088 20.8267 90 96.752 90 ZERR 4 0.0004 0.0008 0.0008 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N O P S UNIT 180 240 16 4 12 12 4 EADP F4A H40 EADP F4C H42 EADP F4B H43 EXYZ F4A H40 EXYZ F4C H42 EXYZ F4B H43 L.S. 20 PLAN 20 SIZE 0.2 0.22 0.35 TEMP 0 LIST 6 FMAP 2 ACTA REM REM REM WGHT 0.050800 1.895800 FVAR 0.34194 P2 6 0.634848 0.519077 0.221463 11.00000 0.01312 0.01479 = 0.01563 -0.00034 0.00474 -0.00044 P3 6 0.461829 0.565979 0.170413 11.00000 0.01572 0.01348 = 0.01504 0.00009 0.00316 -0.00066 P1 6 0.632123 0.597560 0.296377 11.00000 0.01665 0.01519 = 0.01591 -0.00115 0.00452 -0.00246 S1 7 0.314514 0.688549 0.418124 11.00000 0.02901 0.02149 = 0.02107 -0.00346 0.00262 0.00432 O1 5 0.342761 0.622356 0.399611 11.00000 0.04289 0.02202 = 0.03459 -0.00747 0.02125 -0.00241 N1 4 0.467269 0.585677 0.297948 11.00000 0.01683 0.01533 = 0.01704 -0.00164 0.00584 0.00119 F3 3 0.535360 0.721554 0.387974 11.00000 0.05021 0.05030 = 0.12022 -0.01291 0.04065 -0.01844 F1 3 0.466381 0.783957 0.458694 11.00000 0.05694 0.04028 = 0.11853 -0.04058 -0.01220 -0.00652 O2 5 0.261747 0.728812 0.366141 11.00000 0.05354 0.04371 = 0.05391 0.01531 -0.02365 0.00098 O3 5 0.257006 0.692325 0.476360 11.00000 0.06783 0.05412 = 0.04568 -0.01702 0.03214 0.00520 F2 3 0.534500 0.686941 0.484814 11.00000 0.06451 0.08099 = 0.09967 0.00506 -0.05353 0.01040 C20 1 0.804070 0.599757 0.152881 11.00000 0.01758 0.02378 = 0.01656 -0.00258 0.00396 -0.00600 C27 1 0.705092 0.561350 0.372129 11.00000 0.01607 0.01960 = 0.01556 -0.00305 0.00297 0.00005 C9 1 0.379295 0.412687 0.206559 11.00000 0.01855 0.01526 = 0.01720 0.00123 0.00162 -0.00228 AFIX 13 H9 2 0.427087 0.446083 0.232910 11.00000 -1.20000 AFIX 0 C15 1 0.774116 0.539212 0.180315 11.00000 0.01319 0.02159 = 0.01466 -0.00276 0.00272 -0.00156 C3 1 0.363864 0.506427 0.121178 11.00000 0.01334 0.01634 = 0.01507 -0.00077 0.00321 0.00043 C8 1 0.332380 0.442806 0.141600 11.00000 0.01482 0.01640 = 0.01611 -0.00091 0.00440 -0.00008 C4 1 0.317605 0.528488 0.058011 11.00000 0.01586 0.01672 = 0.01621 0.00074 0.00443 0.00234 C7 1 0.254320 0.403496 0.099206 11.00000 0.02182 0.01720 = 0.02176 -0.00078 0.00231 -0.00292 AFIX 43 H7 2 0.233755 0.361598 0.112058 11.00000 -1.20000 AFIX 0 C36 1 0.560298 0.458861 0.374243 11.00000 0.02356 0.01784 = 0.01668 0.00036 0.00421 -0.00252 AFIX 13 H36 2 0.529356 0.474979 0.330948 11.00000 -1.20000 AFIX 0 C1 1 0.392517 0.572673 0.245693 11.00000 0.01616 0.01200 = 0.02012 -0.00032 0.00448 0.00182 C28 1 0.666987 0.503586 0.402407 11.00000 0.01900 0.01901 = 0.01814 -0.00153 0.00440 0.00104 C12 1 0.345947 0.595393 0.030643 11.00000 0.02308 0.01846 = 0.01684 0.00333 0.00343 -0.00124 AFIX 13 H12 2 0.403736 0.618503 0.063026 11.00000 -1.20000 AFIX 0 C16 1 0.857059 0.484673 0.179005 11.00000 0.01319 0.02698 = 0.01798 -0.00215 0.00081 0.00139 C19 1 0.915191 0.603966 0.123809 11.00000 0.01881 0.03476 = 0.01927 -0.00012 0.00472 -0.00908 AFIX 43 H19 2 0.936743 0.643637 0.106076 11.00000 -1.20000 AFIX 0 C24 1 0.722935 0.661034 0.150913 11.00000 0.02677 0.01809 = 0.02561 0.00023 0.01126 -0.00552 AFIX 13 H24 2 0.651724 0.651865 0.175223 11.00000 -1.20000 AFIX 0 C6 1 0.206823 0.425686 0.038294 11.00000 0.02231 0.02235 = 0.01927 -0.00405 -0.00037 -0.00424 AFIX 43 H6 2 0.153213 0.399168 0.011118 11.00000 -1.20000 AFIX 0 C5 1 0.239053 0.487129 0.017949 11.00000 0.02134 0.02277 = 0.01556 0.00039 0.00000 0.00058 AFIX 43 H5 2 0.207797 0.501258 -0.023292 11.00000 -1.20000 AFIX 0 C37 1 0.450441 0.460334 0.415279 11.00000 0.02493 0.02441 = 0.02778 -0.00100 0.00847 -0.00388 AFIX 137 H37A 2 0.478063 0.443581 0.457655 11.00000 -1.50000 H37B 2 0.382727 0.433730 0.395202 11.00000 -1.50000 H37C 2 0.421646 0.504616 0.418712 11.00000 -1.50000 AFIX 0 C2 1 0.253246 0.572330 0.247044 11.00000 0.01583 0.02504 = 0.02775 -0.00275 0.00517 0.00234 AFIX 137 H2A 2 0.213593 0.597580 0.211417 11.00000 -1.50000 H2B 2 0.233703 0.591123 0.286933 11.00000 -1.50000 H2C 2 0.222776 0.528065 0.243652 11.00000 -1.50000 AFIX 0 C32 1 0.810746 0.597816 0.401623 11.00000 0.01733 0.02418 = 0.02433 -0.00423 0.00358 -0.00237 C29 1 0.730850 0.485401 0.462033 11.00000 0.02771 0.02630 = 0.02171 0.00370 0.00164 0.00067 AFIX 43 H29 2 0.705422 0.448107 0.482652 11.00000 -1.20000 AFIX 0 C18 1 0.993843 0.550572 0.120779 11.00000 0.01416 0.04998 = 0.02098 -0.00027 0.00554 -0.00383 AFIX 43 H18 2 1.066164 0.554315 0.100161 11.00000 -1.20000 AFIX 0 C10 1 0.468082 0.355396 0.197057 11.00000 0.02510 0.02145 = 0.02678 -0.00021 -0.00162 0.00373 AFIX 137 H10A 2 0.422717 0.322013 0.171500 11.00000 -1.50000 H10B 2 0.500194 0.337635 0.238418 11.00000 -1.50000 H10C 2 0.536940 0.370659 0.175301 11.00000 -1.50000 AFIX 0 C17 1 0.965465 0.491940 0.148161 11.00000 0.01480 0.04118 = 0.02387 -0.00106 0.00405 0.00602 AFIX 43 H17 2 1.019466 0.456451 0.146107 11.00000 -1.20000 AFIX 0 C21 1 0.838711 0.420063 0.213493 11.00000 0.01794 0.02504 = 0.02966 0.00191 0.00484 0.00621 AFIX 13 H21 2 0.748125 0.414682 0.215647 11.00000 -1.20000 AFIX 0 C30 1 0.831093 0.521677 0.491058 11.00000 0.02840 0.03689 = 0.02360 0.00061 -0.00584 0.00346 AFIX 43 H30 2 0.871622 0.508987 0.531096 11.00000 -1.20000 AFIX 0 C11 1 0.270146 0.389938 0.242546 11.00000 0.02645 0.02608 = 0.02449 0.00724 0.00575 -0.00455 AFIX 137 H11A 2 0.211313 0.425237 0.244509 11.00000 -1.50000 H11B 2 0.302247 0.376809 0.285615 11.00000 -1.50000 H11C 2 0.228407 0.353495 0.220090 11.00000 -1.50000 AFIX 0 C31 1 0.871238 0.576583 0.460906 11.00000 0.02134 0.03398 = 0.03127 -0.00506 -0.00499 -0.00385 AFIX 43 H31 2 0.940114 0.599962 0.480509 11.00000 -1.20000 AFIX 0 C13 1 0.410361 0.588881 -0.031145 11.00000 0.03064 0.03010 = 0.02596 0.00621 0.01275 0.00216 AFIX 137 H13A 2 0.486086 0.563518 -0.022140 11.00000 -1.50000 H13B 2 0.430967 0.631648 -0.045973 11.00000 -1.50000 H13C 2 0.354325 0.567403 -0.063974 11.00000 -1.50000 AFIX 0 C33 1 0.865997 0.656549 0.369795 11.00000 0.02297 0.03038 = 0.03017 -0.00279 0.00311 -0.01053 AFIX 13 H33 2 0.800488 0.674007 0.337412 11.00000 -1.20000 AFIX 0 C38 1 0.607083 0.388456 0.367559 11.00000 0.03458 0.02004 = 0.02919 -0.00156 0.00788 -0.00016 AFIX 137 H38A 2 0.672844 0.387984 0.339856 11.00000 -1.50000 H38B 2 0.538479 0.361411 0.349225 11.00000 -1.50000 H38C 2 0.639224 0.371886 0.409411 11.00000 -1.50000 AFIX 0 C14 1 0.225259 0.636154 0.017472 11.00000 0.03485 0.02081 = 0.03532 0.00587 0.01174 0.00744 AFIX 137 H14A 2 0.165312 0.613141 -0.012299 11.00000 -1.50000 H14B 2 0.244639 0.677592 -0.000813 11.00000 -1.50000 H14C 2 0.190177 0.643277 0.057270 11.00000 -1.50000 AFIX 0 C22 1 0.903331 0.424404 0.283040 11.00000 0.03303 0.03879 = 0.02617 0.00652 0.00737 0.01069 AFIX 137 H22A 2 0.991566 0.433008 0.282503 11.00000 -1.50000 H22B 2 0.892830 0.383704 0.304888 11.00000 -1.50000 H22C 2 0.866088 0.459221 0.305307 11.00000 -1.50000 AFIX 0 C26 1 0.669195 0.677324 0.081180 11.00000 0.03541 0.03439 = 0.03198 0.00917 0.01112 0.00708 AFIX 137 H26A 2 0.736198 0.691381 0.057461 11.00000 -1.50000 H26B 2 0.607960 0.711731 0.081398 11.00000 -1.50000 H26C 2 0.629795 0.639052 0.061040 11.00000 -1.50000 AFIX 0 C25 1 0.794296 0.719881 0.182686 11.00000 0.04494 0.02448 = 0.04884 -0.00755 0.01689 -0.01444 AFIX 137 H25A 2 0.824176 0.709510 0.226795 11.00000 -1.50000 H25B 2 0.738825 0.756985 0.181497 11.00000 -1.50000 H25C 2 0.864646 0.730059 0.159696 11.00000 -1.50000 AFIX 0 C23 1 0.884299 0.359664 0.179404 11.00000 0.03995 0.03142 = 0.03761 -0.00279 0.00226 0.01345 AFIX 137 H23A 2 0.848026 0.359626 0.134986 11.00000 -1.50000 H23B 2 0.858920 0.320761 0.200331 11.00000 -1.50000 H23C 2 0.974547 0.360715 0.181510 11.00000 -1.50000 AFIX 0 C39 1 0.469293 0.722060 0.438634 11.00000 0.03356 0.02898 = 0.05462 -0.00807 -0.01092 0.00369 C35 1 0.976240 0.634210 0.334371 11.00000 0.03733 0.04941 = 0.04167 -0.01079 0.01750 -0.01637 AFIX 137 H35A 2 1.040026 0.614641 0.364707 11.00000 -1.50000 H35B 2 1.011002 0.671308 0.314337 11.00000 -1.50000 H35C 2 0.946835 0.602672 0.301853 11.00000 -1.50000 AFIX 0 C34 1 0.907350 0.711893 0.417181 11.00000 0.05099 0.03186 = 0.04737 -0.01099 0.01567 -0.01774 AFIX 137 H34A 2 0.839064 0.723110 0.441250 11.00000 -1.50000 H34B 2 0.930507 0.749556 0.393609 11.00000 -1.50000 H34C 2 0.978416 0.697727 0.446408 11.00000 -1.50000 AFIX 0 PART 4 F4B 3 0.975979 0.680766 0.596844 10.40000 0.04345 F4A 3 0.615817 0.782254 0.703795 10.30000 0.04383 PART 0 H1 2 0.434505 0.599417 0.330815 11.00000 0.02946 C45 1 0.670531 0.730886 0.621484 11.00000 0.04564 0.04066 = 0.04907 0.02200 -0.00184 -0.01026 AFIX 43 H45 2 0.588114 0.729275 0.601358 11.00000 -1.20000 AFIX 0 C41 1 0.819934 0.764926 0.710883 11.00000 0.07027 0.02272 = 0.04632 0.00855 -0.00514 -0.01450 AFIX 43 H41 2 0.837347 0.785223 0.750917 11.00000 -1.20000 AFIX 0 C44 1 0.766285 0.702823 0.592542 11.00000 0.05290 0.03972 = 0.03618 0.01483 -0.00432 -0.00946 AFIX 43 H44 2 0.749059 0.681183 0.553198 11.00000 -1.20000 AFIX 0 C43 1 0.887926 0.707002 0.622264 11.00000 0.05135 0.03584 = 0.04839 0.01556 0.00248 -0.00368 C40 1 0.697061 0.761519 0.680602 11.00000 0.06356 0.02916 = 0.05493 0.01448 0.00694 -0.00807 C42 1 0.915028 0.737917 0.680837 11.00000 0.05045 0.03128 = 0.05474 0.01433 -0.01034 -0.01326 PART 4 F4C 3 1.015502 0.745875 0.706686 10.30000 0.07441 PART 0 PART 5 H40 2 0.615817 0.782254 0.703795 10.70000 0.04383 H42 2 1.015502 0.745875 0.706686 10.70000 0.07441 H43 2 0.975979 0.680766 0.596844 10.60000 0.04345 HKLF 4 REM im047_a.res in P2(1)/n REM wR2 = 0.1094, GooF = S = 1.026, Restrained GooF = 1.026 for all data REM R1 = 0.0408 for 10809 Fo > 4sig(Fo) and 0.0575 for all 13812 data REM 534 parameters refined using 0 restraints END WGHT 0.0508 1.8955 REM Highest difference peak 0.658, deepest hole -0.470, 1-sigma level 0.057 Q1 1 0.3964 0.7040 0.4279 11.00000 0.05 0.66 Q2 1 0.3319 0.7016 0.4903 11.00000 0.05 0.44 Q3 1 0.3302 0.5613 0.0443 11.00000 0.05 0.40 Q4 1 0.3224 0.5215 0.0952 11.00000 0.05 0.39 Q5 1 0.2830 0.5046 0.0393 11.00000 0.05 0.39 Q6 1 0.5801 0.7153 0.4489 11.00000 0.05 0.39 Q7 1 0.2403 0.4178 0.0684 11.00000 0.05 0.39 Q8 1 0.2230 0.4596 0.0343 11.00000 0.05 0.38 Q9 1 0.2422 0.7192 0.4499 11.00000 0.05 0.37 Q10 1 0.6135 0.4790 0.3917 11.00000 0.05 0.36 Q11 1 0.8569 0.6030 0.1393 11.00000 0.05 0.36 Q12 1 0.3241 0.7189 0.3921 11.00000 0.05 0.36 Q13 1 0.2931 0.6226 0.0283 11.00000 0.05 0.36 Q14 1 0.8476 0.5825 0.4271 11.00000 0.05 0.35 Q15 1 0.4299 0.5718 0.2061 11.00000 0.05 0.35 Q16 1 0.3242 0.7363 0.3501 11.00000 0.05 0.34 Q17 1 0.7016 0.4960 0.4341 11.00000 0.05 0.34 Q18 1 0.7815 0.5652 0.1591 11.00000 0.05 0.34 Q19 1 0.4919 0.6010 0.1721 11.00000 0.05 0.34 Q20 1 0.3383 0.4796 0.1299 11.00000 0.05 0.34 ; _shelx_res_checksum 72347 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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' 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 P2 P 0.63485(3) 0.51908(2) 0.22146(2) 0.01427(7) Uani 1 1 d . . . . . P3 P 0.46183(3) 0.56598(2) 0.17041(2) 0.01464(7) Uani 1 1 d . . . . . P1 P 0.63212(3) 0.59756(2) 0.29638(2) 0.01571(7) Uani 1 1 d . . . . . S1 S 0.31451(4) 0.68855(2) 0.41812(2) 0.02388(8) Uani 1 1 d . . . . . O1 O 0.34276(12) 0.62236(5) 0.39961(6) 0.0318(3) Uani 1 1 d . . . . . N1 N 0.46727(11) 0.58568(5) 0.29795(5) 0.0161(2) Uani 1 1 d . . . . . F3 F 0.53536(13) 0.72155(7) 0.38797(9) 0.0711(5) Uani 1 1 d . . . . . F1 F 0.46638(13) 0.78396(6) 0.45869(9) 0.0737(5) Uani 1 1 d . . . . . O2 O 0.26175(14) 0.72881(7) 0.36614(8) 0.0528(4) Uani 1 1 d . . . . . O3 O 0.25701(16) 0.69233(8) 0.47636(7) 0.0539(4) Uani 1 1 d . . . . . F2 F 0.53450(15) 0.68694(8) 0.48481(9) 0.0867(6) Uani 1 1 d . . . . . C20 C 0.80407(13) 0.59976(7) 0.15288(6) 0.0192(3) Uani 1 1 d . . . . . C27 C 0.70509(12) 0.56135(6) 0.37213(6) 0.0170(2) Uani 1 1 d . . . . . C9 C 0.37930(13) 0.41269(6) 0.20656(6) 0.0170(2) Uani 1 1 d . . . . . H9 H 0.427087 0.446083 0.232910 0.020 Uiso 1 1 calc R U . . . C15 C 0.77412(12) 0.53921(7) 0.18031(6) 0.0164(2) Uani 1 1 d . . . . . C3 C 0.36386(12) 0.50643(6) 0.12118(6) 0.0148(2) Uani 1 1 d . . . . . C8 C 0.33238(12) 0.44281(6) 0.14160(6) 0.0156(2) Uani 1 1 d . . . . . C4 C 0.31761(12) 0.52849(6) 0.05801(6) 0.0161(2) Uani 1 1 d . . . . . C7 C 0.25432(13) 0.40350(7) 0.09921(7) 0.0203(3) Uani 1 1 d . . . . . H7 H 0.233755 0.361598 0.112058 0.024 Uiso 1 1 calc R U . . . C36 C 0.56030(13) 0.45886(7) 0.37424(7) 0.0192(3) Uani 1 1 d . . . . . H36 H 0.529356 0.474979 0.330948 0.023 Uiso 1 1 calc R U . . . C1 C 0.39252(12) 0.57267(6) 0.24569(6) 0.0159(2) Uani 1 1 d . . . . . C28 C 0.66699(13) 0.50359(7) 0.40241(6) 0.0185(3) Uani 1 1 d . . . . . C12 C 0.34595(13) 0.59539(7) 0.03064(7) 0.0194(3) Uani 1 1 d . . . . . H12 H 0.403736 0.618503 0.063026 0.023 Uiso 1 1 calc R U . . . C16 C 0.85706(12) 0.48467(7) 0.17901(7) 0.0195(3) Uani 1 1 d . . . . . C19 C 0.91519(13) 0.60397(8) 0.12381(7) 0.0241(3) Uani 1 1 d . . . . . H19 H 0.936743 0.643637 0.106076 0.029 Uiso 1 1 calc R U . . . C24 C 0.72294(14) 0.66103(7) 0.15091(7) 0.0228(3) Uani 1 1 d . . . . . H24 H 0.651724 0.651865 0.175223 0.027 Uiso 1 1 calc R U . . . C6 C 0.20682(14) 0.42569(7) 0.03829(7) 0.0215(3) Uani 1 1 d . . . . . H6 H 0.153213 0.399168 0.011118 0.026 Uiso 1 1 calc R U . . . C5 C 0.23905(13) 0.48713(7) 0.01795(6) 0.0201(3) Uani 1 1 d . . . . . H5 H 0.207797 0.501258 -0.023292 0.024 Uiso 1 1 calc R U . . . C37 C 0.45044(14) 0.46033(7) 0.41528(8) 0.0253(3) Uani 1 1 d . . . . . H37A H 0.478063 0.443581 0.457655 0.038 Uiso 1 1 calc R U . . . H37B H 0.382727 0.433730 0.395202 0.038 Uiso 1 1 calc R U . . . H37C H 0.421646 0.504616 0.418712 0.038 Uiso 1 1 calc R U . . . C2 C 0.25325(13) 0.57233(7) 0.24704(7) 0.0227(3) Uani 1 1 d . . . . . H2A H 0.213593 0.597580 0.211417 0.034 Uiso 1 1 calc R U . . . H2B H 0.233703 0.591123 0.286933 0.034 Uiso 1 1 calc R U . . . H2C H 0.222776 0.528065 0.243652 0.034 Uiso 1 1 calc R U . . . C32 C 0.81075(13) 0.59782(7) 0.40162(7) 0.0219(3) Uani 1 1 d . . . . . C29 C 0.73085(15) 0.48540(8) 0.46203(7) 0.0253(3) Uani 1 1 d . . . . . H29 H 0.705422 0.448107 0.482652 0.030 Uiso 1 1 calc R U . . . C18 C 0.99384(13) 0.55057(9) 0.12078(7) 0.0281(3) Uani 1 1 d . . . . . H18 H 1.066164 0.554315 0.100161 0.034 Uiso 1 1 calc R U . . . C10 C 0.46808(14) 0.35540(7) 0.19706(8) 0.0248(3) Uani 1 1 d . . . . . H10A H 0.422717 0.322013 0.171500 0.037 Uiso 1 1 calc R U . . . H10B H 0.500194 0.337635 0.238418 0.037 Uiso 1 1 calc R U . . . H10C H 0.536940 0.370659 0.175301 0.037 Uiso 1 1 calc R U . . . C17 C 0.96547(13) 0.49194(9) 0.14816(7) 0.0265(3) Uani 1 1 d . . . . . H17 H 1.019466 0.456451 0.146107 0.032 Uiso 1 1 calc R U . . . C21 C 0.83871(14) 0.42006(7) 0.21349(7) 0.0240(3) Uani 1 1 d . . . . . H21 H 0.748125 0.414682 0.215647 0.029 Uiso 1 1 calc R U . . . C30 C 0.83109(15) 0.52168(8) 0.49106(8) 0.0303(3) Uani 1 1 d . . . . . H30 H 0.871622 0.508987 0.531096 0.036 Uiso 1 1 calc R U . . . C11 C 0.27015(15) 0.38994(8) 0.24255(7) 0.0255(3) Uani 1 1 d . . . . . H11A H 0.211313 0.425237 0.244509 0.038 Uiso 1 1 calc R U . . . H11B H 0.302247 0.376809 0.285615 0.038 Uiso 1 1 calc R U . . . H11C H 0.228407 0.353495 0.220090 0.038 Uiso 1 1 calc R U . . . C31 C 0.87124(15) 0.57658(8) 0.46091(8) 0.0295(3) Uani 1 1 d . . . . . H31 H 0.940114 0.599962 0.480509 0.035 Uiso 1 1 calc R U . . . C13 C 0.41036(15) 0.58888(8) -0.03115(8) 0.0281(3) Uani 1 1 d . . . . . H13A H 0.486086 0.563518 -0.022140 0.042 Uiso 1 1 calc R U . . . H13B H 0.430967 0.631648 -0.045973 0.042 Uiso 1 1 calc R U . . . H13C H 0.354325 0.567403 -0.063974 0.042 Uiso 1 1 calc R U . . . C33 C 0.86600(15) 0.65655(8) 0.36980(8) 0.0278(3) Uani 1 1 d . . . . . H33 H 0.800488 0.674007 0.337412 0.033 Uiso 1 1 calc R U . . . C38 C 0.60708(16) 0.38846(7) 0.36756(8) 0.0276(3) Uani 1 1 d . . . . . H38A H 0.672844 0.387984 0.339856 0.041 Uiso 1 1 calc R U . . . H38B H 0.538479 0.361411 0.349225 0.041 Uiso 1 1 calc R U . . . H38C H 0.639224 0.371886 0.409411 0.041 Uiso 1 1 calc R U . . . C14 C 0.22526(16) 0.63615(8) 0.01747(8) 0.0297(3) Uani 1 1 d . . . . . H14A H 0.165312 0.613141 -0.012299 0.045 Uiso 1 1 calc R U . . . H14B H 0.244639 0.677592 -0.000813 0.045 Uiso 1 1 calc R U . . . H14C H 0.190177 0.643277 0.057270 0.045 Uiso 1 1 calc R U . . . C22 C 0.90333(17) 0.42440(9) 0.28304(8) 0.0324(4) Uani 1 1 d . . . . . H22A H 0.991566 0.433008 0.282503 0.049 Uiso 1 1 calc R U . . . H22B H 0.892830 0.383704 0.304888 0.049 Uiso 1 1 calc R U . . . H22C H 0.866088 0.459221 0.305307 0.049 Uiso 1 1 calc R U . . . C26 C 0.66919(17) 0.67732(9) 0.08118(8) 0.0334(4) Uani 1 1 d . . . . . H26A H 0.736198 0.691381 0.057461 0.050 Uiso 1 1 calc R U . . . H26B H 0.607960 0.711731 0.081398 0.050 Uiso 1 1 calc R U . . . H26C H 0.629795 0.639052 0.061040 0.050 Uiso 1 1 calc R U . . . C25 C 0.79430(19) 0.71988(8) 0.18269(10) 0.0385(4) Uani 1 1 d . . . . . H25A H 0.824176 0.709510 0.226795 0.058 Uiso 1 1 calc R U . . . H25B H 0.738825 0.756985 0.181497 0.058 Uiso 1 1 calc R U . . . H25C H 0.864646 0.730059 0.159696 0.058 Uiso 1 1 calc R U . . . C23 C 0.88430(18) 0.35966(9) 0.17940(9) 0.0365(4) Uani 1 1 d . . . . . H23A H 0.848026 0.359626 0.134986 0.055 Uiso 1 1 calc R U . . . H23B H 0.858920 0.320761 0.200331 0.055 Uiso 1 1 calc R U . . . H23C H 0.974547 0.360715 0.181510 0.055 Uiso 1 1 calc R U . . . C39 C 0.46929(18) 0.72206(9) 0.43863(10) 0.0403(4) Uani 1 1 d . . . . . C35 C 0.97624(18) 0.63421(10) 0.33437(10) 0.0418(4) Uani 1 1 d . . . . . H35A H 1.040026 0.614641 0.364707 0.063 Uiso 1 1 calc R U . . . H35B H 1.011002 0.671308 0.314337 0.063 Uiso 1 1 calc R U . . . H35C H 0.946835 0.602672 0.301853 0.063 Uiso 1 1 calc R U . . . C34 C 0.9073(2) 0.71189(9) 0.41718(10) 0.0426(5) Uani 1 1 d . . . . . H34A H 0.839064 0.723110 0.441250 0.064 Uiso 1 1 calc R U . . . H34B H 0.930507 0.749556 0.393609 0.064 Uiso 1 1 calc R U . . . H34C H 0.978416 0.697727 0.446408 0.064 Uiso 1 1 calc R U . . . F4B F 0.9760(3) 0.68077(13) 0.59684(13) 0.0435(6) Uiso 0.4 1 d . . P A 4 F4A F 0.6158(3) 0.78225(17) 0.70379(17) 0.0438(8) Uiso 0.3 1 d . . P B 4 H1 H 0.4345(18) 0.5994(9) 0.3308(9) 0.029(5) Uiso 1 1 d . . . . . C45 C 0.6705(2) 0.73089(10) 0.62148(11) 0.0457(5) Uani 1 1 d . . . . . H45 H 0.588114 0.729275 0.601358 0.055 Uiso 1 1 calc R U . . . C41 C 0.8199(2) 0.76493(9) 0.71088(11) 0.0474(5) Uani 1 1 d . . . . . H41 H 0.837347 0.785223 0.750917 0.057 Uiso 1 1 calc R U . . . C44 C 0.7663(2) 0.70282(10) 0.59254(10) 0.0437(5) Uani 1 1 d . . . . . H44 H 0.749059 0.681183 0.553198 0.052 Uiso 1 1 calc R U . . . C43 C 0.8879(2) 0.70700(10) 0.62226(11) 0.0455(5) Uani 1 1 d . . . . . C40 C 0.6971(2) 0.76152(10) 0.68060(11) 0.0492(5) Uani 1 1 d . . . . . C42 C 0.9150(2) 0.73792(9) 0.68084(11) 0.0468(5) Uani 1 1 d . . . . . F4C F 1.0155(5) 0.7459(2) 0.7067(2) 0.0744(13) Uiso 0.3 1 d . . P C 4 H40 H 0.6158(3) 0.78225(17) 0.70379(17) 0.0438(8) Uiso 0.7 1 d . . P D 5 H42 H 1.0155(5) 0.7459(2) 0.7067(2) 0.0744(13) Uiso 0.7 1 d . . P E 5 H43 H 0.9760(3) 0.68077(13) 0.59684(13) 0.0435(6) Uiso 0.6 1 d . . P F 5 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 P2 0.01312(15) 0.01479(14) 0.01563(15) -0.00034(11) 0.00474(11) -0.00044(11) P3 0.01572(15) 0.01348(14) 0.01504(15) 0.00009(11) 0.00316(12) -0.00066(12) P1 0.01665(16) 0.01519(15) 0.01591(15) -0.00115(12) 0.00452(12) -0.00246(12) S1 0.02901(19) 0.02149(16) 0.02107(16) -0.00346(13) 0.00262(14) 0.00432(14) O1 0.0429(7) 0.0220(5) 0.0346(6) -0.0075(4) 0.0213(5) -0.0024(5) N1 0.0168(5) 0.0153(5) 0.0170(5) -0.0016(4) 0.0058(4) 0.0012(4) F3 0.0502(8) 0.0503(8) 0.1202(13) -0.0129(8) 0.0406(8) -0.0184(6) F1 0.0569(8) 0.0403(7) 0.1185(13) -0.0406(8) -0.0122(8) -0.0065(6) O2 0.0535(9) 0.0437(8) 0.0539(9) 0.0153(7) -0.0237(7) 0.0010(7) O3 0.0678(10) 0.0541(9) 0.0457(8) -0.0170(7) 0.0321(7) 0.0052(8) F2 0.0645(10) 0.0810(11) 0.0997(13) 0.0051(9) -0.0535(9) 0.0104(8) C20 0.0176(6) 0.0238(6) 0.0166(6) -0.0026(5) 0.0040(5) -0.0060(5) C27 0.0161(6) 0.0196(6) 0.0156(6) -0.0030(5) 0.0030(5) 0.0001(5) C9 0.0186(6) 0.0153(6) 0.0172(6) 0.0012(5) 0.0016(5) -0.0023(5) C15 0.0132(6) 0.0216(6) 0.0147(6) -0.0028(5) 0.0027(4) -0.0016(5) C3 0.0133(5) 0.0163(6) 0.0151(5) -0.0008(4) 0.0032(4) 0.0004(4) C8 0.0148(6) 0.0164(6) 0.0161(6) -0.0009(4) 0.0044(4) -0.0001(5) C4 0.0159(6) 0.0167(6) 0.0162(6) 0.0007(5) 0.0044(5) 0.0023(5) C7 0.0218(7) 0.0172(6) 0.0218(6) -0.0008(5) 0.0023(5) -0.0029(5) C36 0.0236(7) 0.0178(6) 0.0167(6) 0.0004(5) 0.0042(5) -0.0025(5) C1 0.0162(6) 0.0120(5) 0.0201(6) -0.0003(4) 0.0045(5) 0.0018(4) C28 0.0190(6) 0.0190(6) 0.0181(6) -0.0015(5) 0.0044(5) 0.0010(5) C12 0.0231(7) 0.0185(6) 0.0168(6) 0.0033(5) 0.0034(5) -0.0012(5) C16 0.0132(6) 0.0270(7) 0.0180(6) -0.0022(5) 0.0008(5) 0.0014(5) C19 0.0188(6) 0.0348(8) 0.0193(6) -0.0001(6) 0.0047(5) -0.0091(6) C24 0.0268(7) 0.0181(6) 0.0256(7) 0.0002(5) 0.0113(6) -0.0055(5) C6 0.0223(7) 0.0224(6) 0.0193(6) -0.0040(5) -0.0004(5) -0.0042(5) C5 0.0213(6) 0.0228(6) 0.0156(6) 0.0004(5) 0.0000(5) 0.0006(5) C37 0.0249(7) 0.0244(7) 0.0278(7) -0.0010(6) 0.0085(6) -0.0039(6) C2 0.0158(6) 0.0250(7) 0.0277(7) -0.0027(6) 0.0052(5) 0.0023(5) C32 0.0173(6) 0.0242(7) 0.0243(7) -0.0042(5) 0.0036(5) -0.0024(5) C29 0.0277(7) 0.0263(7) 0.0217(7) 0.0037(6) 0.0016(6) 0.0007(6) C18 0.0142(6) 0.0500(10) 0.0210(7) -0.0003(6) 0.0055(5) -0.0038(6) C10 0.0251(7) 0.0214(7) 0.0268(7) -0.0002(5) -0.0016(6) 0.0037(6) C17 0.0148(6) 0.0412(9) 0.0239(7) -0.0011(6) 0.0040(5) 0.0060(6) C21 0.0179(6) 0.0250(7) 0.0297(7) 0.0019(6) 0.0048(5) 0.0062(5) C30 0.0284(8) 0.0369(9) 0.0236(7) 0.0006(6) -0.0058(6) 0.0035(7) C11 0.0264(7) 0.0261(7) 0.0245(7) 0.0072(6) 0.0058(6) -0.0045(6) C31 0.0213(7) 0.0340(8) 0.0313(8) -0.0051(6) -0.0050(6) -0.0039(6) C13 0.0306(8) 0.0301(8) 0.0260(7) 0.0062(6) 0.0127(6) 0.0022(6) C33 0.0230(7) 0.0304(8) 0.0302(8) -0.0028(6) 0.0031(6) -0.0105(6) C38 0.0346(8) 0.0200(7) 0.0292(8) -0.0016(6) 0.0079(6) -0.0002(6) C14 0.0348(8) 0.0208(7) 0.0353(8) 0.0059(6) 0.0117(7) 0.0074(6) C22 0.0330(8) 0.0388(9) 0.0262(8) 0.0065(7) 0.0074(6) 0.0107(7) C26 0.0354(9) 0.0344(8) 0.0320(8) 0.0092(7) 0.0111(7) 0.0071(7) C25 0.0449(10) 0.0245(8) 0.0488(11) -0.0075(7) 0.0169(8) -0.0144(7) C23 0.0400(10) 0.0314(8) 0.0376(9) -0.0028(7) 0.0023(7) 0.0135(7) C39 0.0336(9) 0.0290(8) 0.0546(12) -0.0081(8) -0.0109(8) 0.0037(7) C35 0.0373(10) 0.0494(11) 0.0417(10) -0.0108(8) 0.0175(8) -0.0164(8) C34 0.0510(11) 0.0319(9) 0.0474(11) -0.0110(8) 0.0157(9) -0.0177(8) C45 0.0456(11) 0.0407(10) 0.0491(12) 0.0220(9) -0.0018(9) -0.0103(9) C41 0.0703(15) 0.0227(8) 0.0463(11) 0.0085(8) -0.0051(10) -0.0145(9) C44 0.0529(12) 0.0397(10) 0.0362(10) 0.0148(8) -0.0043(9) -0.0095(9) C43 0.0514(12) 0.0358(10) 0.0484(11) 0.0156(9) 0.0025(9) -0.0037(9) C40 0.0636(14) 0.0292(9) 0.0549(13) 0.0145(9) 0.0069(11) -0.0081(9) C42 0.0505(12) 0.0313(9) 0.0547(12) 0.0143(9) -0.0103(10) -0.0133(9) 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 P3 P2 P1 86.982(17) . . ? C15 P2 P3 110.46(5) . . ? C15 P2 P1 103.96(4) . . ? C3 P3 P2 111.53(4) . . ? C1 P3 P2 91.13(4) . . ? C1 P3 C3 105.58(6) . . ? N1 P1 P2 90.53(4) . . ? N1 P1 C27 104.52(6) . . ? C27 P1 P2 105.82(4) . . ? O1 S1 C39 101.79(8) . . ? O2 S1 O1 114.41(9) . . ? O2 S1 O3 116.43(10) . . ? O2 S1 C39 103.46(9) . . ? O3 S1 O1 113.69(8) . . ? O3 S1 C39 104.73(10) . . ? C1 N1 P1 121.59(9) . . ? C15 C20 C24 125.09(12) . . ? C19 C20 C15 118.23(13) . . ? C19 C20 C24 116.66(12) . . ? C28 C27 P1 127.08(10) . . ? C28 C27 C32 119.67(13) . . ? C32 C27 P1 113.25(10) . . ? C8 C9 C10 109.79(11) . . ? C8 C9 C11 111.66(11) . . ? C11 C9 C10 110.50(12) . . ? C20 C15 P2 127.91(10) . . ? C20 C15 C16 120.28(12) . . ? C16 C15 P2 111.80(10) . . ? C8 C3 P3 125.30(10) . . ? C8 C3 C4 119.86(12) . . ? C4 C3 P3 114.84(9) . . ? C3 C8 C9 124.97(11) . . ? C7 C8 C9 116.22(11) . . ? C7 C8 C3 118.80(12) . . ? C3 C4 C12 124.53(12) . . ? C5 C4 C3 118.71(12) . . ? C5 C4 C12 116.76(12) . . ? C6 C7 C8 121.25(13) . . ? C28 C36 C37 111.17(11) . . ? C28 C36 C38 111.08(12) . . ? C37 C36 C38 110.40(12) . . ? N1 C1 P3 117.76(10) . . ? N1 C1 C2 120.09(12) . . ? C2 C1 P3 121.65(10) . . ? C27 C28 C36 124.58(12) . . ? C29 C28 C27 118.74(13) . . ? C29 C28 C36 116.67(12) . . ? C4 C12 C13 111.37(12) . . ? C4 C12 C14 110.71(12) . . ? C14 C12 C13 110.35(12) . . ? C15 C16 C21 123.49(12) . . ? C17 C16 C15 118.48(13) . . ? C17 C16 C21 117.89(13) . . ? C18 C19 C20 121.55(14) . . ? C20 C24 C26 110.65(12) . . ? C20 C24 C25 112.38(14) . . ? C25 C24 C26 110.56(13) . . ? C5 C6 C7 120.02(13) . . ? C6 C5 C4 121.34(13) . . ? C27 C32 C33 123.37(13) . . ? C31 C32 C27 118.64(13) . . ? C31 C32 C33 117.88(13) . . ? C30 C29 C28 121.32(14) . . ? C17 C18 C19 120.17(13) . . ? C18 C17 C16 121.23(14) . . ? C16 C21 C22 109.07(13) . . ? C16 C21 C23 114.36(13) . . ? C23 C21 C22 110.65(13) . . ? C31 C30 C29 120.22(15) . . ? C30 C31 C32 121.34(14) . . ? C32 C33 C35 109.57(14) . . ? C32 C33 C34 113.43(14) . . ? C34 C33 C35 110.52(14) . . ? F3 C39 S1 111.50(14) . . ? F1 C39 S1 112.42(13) . . ? F1 C39 F3 106.79(18) . . ? F2 C39 S1 110.89(15) . . ? F2 C39 F3 106.66(18) . . ? F2 C39 F1 108.30(17) . . ? C44 C45 C40 119.7(2) . . ? C42 C41 C40 119.0(2) . . ? C45 C44 C43 119.4(2) . . ? F4B C43 C44 120.0(2) . . ? F4B C43 C42 118.8(2) . . ? C42 C43 C44 121.2(2) . . ? F4A C40 C45 117.8(3) . . ? F4A C40 C41 121.5(3) . . ? C45 C40 C41 120.8(2) . . ? C41 C42 C43 120.0(2) . . ? F4C C42 C41 115.4(3) . . ? F4C C42 C43 124.5(3) . . ? 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 P2 P3 2.2360(5) . ? P2 P1 2.2386(5) . ? P2 C15 1.8482(13) . ? P3 C3 1.8361(13) . ? P3 C1 1.8160(13) . ? P1 N1 1.7815(12) . ? P1 C27 1.8312(14) . ? S1 O1 1.4464(11) . ? S1 O2 1.4218(14) . ? S1 O3 1.4246(13) . ? S1 C39 1.7936(19) . ? N1 C1 1.2992(18) . ? F3 C39 1.337(3) . ? F1 C39 1.332(2) . ? F2 C39 1.329(2) . ? C20 C15 1.4137(19) . ? C20 C19 1.3970(18) . ? C20 C24 1.519(2) . ? C27 C28 1.4190(19) . ? C27 C32 1.4288(19) . ? C9 C8 1.5165(18) . ? C9 C10 1.5329(19) . ? C9 C11 1.5303(19) . ? C15 C16 1.4248(19) . ? C3 C8 1.4190(17) . ? C3 C4 1.4229(18) . ? C8 C7 1.3947(19) . ? C4 C12 1.5237(18) . ? C4 C5 1.3957(19) . ? C7 C6 1.386(2) . ? C36 C28 1.5227(19) . ? C36 C37 1.5310(19) . ? C36 C38 1.533(2) . ? C1 C2 1.4911(18) . ? C28 C29 1.395(2) . ? C12 C13 1.5346(19) . ? C12 C14 1.532(2) . ? C16 C17 1.3965(19) . ? C16 C21 1.525(2) . ? C19 C18 1.382(2) . ? C24 C26 1.534(2) . ? C24 C25 1.531(2) . ? C6 C5 1.380(2) . ? C32 C31 1.394(2) . ? C32 C33 1.522(2) . ? C29 C30 1.381(2) . ? C18 C17 1.375(2) . ? C21 C22 1.532(2) . ? C21 C23 1.530(2) . ? C30 C31 1.377(2) . ? C33 C35 1.531(2) . ? C33 C34 1.530(2) . ? F4B C43 1.252(3) . ? F4A C40 1.124(4) . ? C45 C44 1.372(3) . ? C45 C40 1.380(3) . ? C41 C40 1.389(3) . ? C41 C42 1.370(3) . ? C44 C43 1.375(3) . ? C43 C42 1.374(3) . ? C42 F4C 1.154(5) . ?