#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:05:45 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247599 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125650.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_7125650 loop_ _publ_author_name 'Bousfiha, Asmae' 'Dim\'e, Abdou K D' 'Mankou-Makaya, Amelle' 'Echaubard, Julie' 'Berthelot, Mathieu' 'Cattey, H\'el\`ene' 'Romieu, Anthony' 'Roger, Julien' 'Devillers, Charles H.' _publ_section_title ; Regioselective C-H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation. ; _journal_issue 6 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 884 _journal_page_last 887 _journal_paper_doi 10.1039/c9cc07351e _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C41 H50 N5 O Zn, B F4, 2(C H2 Cl2), 0.63(O H2)' _chemical_formula_sum 'C43 H55.26 B Cl4 F4 N5 O1.63 Zn' _chemical_formula_weight 962.24 _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' _symmetry_space_group_name_Hall '-P 2yn' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-05-09 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-11 deposited with the CCDC. 2019-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.255(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.0207(5) _cell_length_b 15.2513(8) _cell_length_c 27.7168(15) _cell_measurement_reflns_used 9571 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 2.98 _cell_volume 4598.0(4) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2016)' _computing_data_collection 'APEX3 (Bruker, 2015)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector CMOS _diffrn_detector_area_resol_mean '1024 x 1024' _diffrn_detector_type 'Photon 100' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device '\k-geometry diffractometer triump Mo' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\f and \w scans'' _diffrn_radiation_collimation '0.6 mm' _diffrn_radiation_monochromator 'TRIUMPH curved crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_unetI/netI 0.0207 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 92164 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.553 _diffrn_reflns_theta_min 2.899 _diffrn_source 'X-ray tube' _diffrn_source_target Mo _diffrn_source_type 'Siemens KFF Mo 2K-90C' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0544 before and 0.0463 after correction. The Ratio of minimum to maximum transmission is 0.9293.' _exptl_crystal_colour 'clear light red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.390 _exptl_crystal_description prism _exptl_crystal_F_000 2001 _exptl_crystal_recrystallization_method 'The material was recrystallised from a mixture of heptane and DCM by slow evaporation' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.2 _refine_diff_density_max 3.526 _refine_diff_density_min -1.742 _refine_diff_density_rms 0.121 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 590 _refine_ls_number_reflns 10589 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0765 _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^)+(0.1171P)^2^+17.3008P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2048 _refine_ls_wR_factor_ref 0.2184 _reflns_Friedel_coverage 0.000 _reflns_number_gt 8936 _reflns_number_total 10589 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc07351e2.cif _cod_data_source_block ZnTTBPPyBF4 _cod_depositor_comments 'Adding full bibliography for 7125649--7125650.cif.' _cod_database_code 7125650 _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 0.853 _shelx_estimated_absorpt_t_min 0.796 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Others Fixed Sof: B2(0.67) F3(0.67) F4(0.67) F5(0.67) F6(0.67) B2A(0.33) F3A(0.33) F4A(0.33) F5A(0.33) F6A(0.33) O2(0.63) 3.a Free rotating group: B2(F3,F4,F5,F6) 3.b Rotating group: O1(H1A,H1B) 3.c Secondary CH2 refined with riding coordinates: C44(H44A,H44B), C42(H42A,H42B) 3.d Aromatic/amide H refined with riding coordinates: C3(H3), C6(H6), C8(H8), C11(H11), C13(H13), C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25) 3.e Idealised Me refined as rotating group: C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B, H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A, H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C) ; _shelx_res_file ; TITL 1905cd85_0m_a.res in P2(1)/n 1905cd85_0m_a.res created by SHELXL-2018/3 at 15:33:21 on 10-Oct-2019 REM Old TITL 1905cd85_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.208, Rweak 0.009, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C44 B6 F6 N5 Zn CELL 0.71073 11.0207 15.2513 27.7168 90 99.255 90 ZERR 4 0.0005 0.0008 0.0015 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H B Cl F N O Zn UNIT 172 221.04 4 16 16 20 6.52 4 L.S. 10 PLAN 20 SIZE 0.28 0.2 0.29 TEMP -173.15 LIST 4 CONF BOND $H HTAB fmap 2 acta OMIT 2 0 2 OMIT 2 0 4 OMIT -3 1 5 OMIT -1 3 9 OMIT -5 4 4 OMIT -4 1 8 OMIT 3 0 5 OMIT 0 7 2 REM REM REM WGHT 0.117100 17.300798 FVAR 0.25791 O1 7 0.584145 0.224067 0.284559 11.00000 0.02099 0.02830 = 0.03510 0.00488 0.00729 0.00249 AFIX 7 H1A 2 0.534285 0.178217 0.268959 11.00000 -1.50000 H1B 2 0.592596 0.205907 0.317669 11.00000 -1.50000 AFIX 0 ZN 8 0.500731 0.353936 0.271373 11.00000 0.01593 0.02001 = 0.01393 0.00022 0.00354 -0.00173 C1 1 0.214110 0.267420 0.270375 11.00000 0.01483 0.02047 = 0.02191 -0.00007 0.00192 -0.00003 N1 6 0.388132 0.338704 0.322960 11.00000 0.01748 0.02717 = 0.01567 -0.00061 0.00352 -0.00230 C2 1 0.274991 0.300789 0.315174 11.00000 0.01777 0.02132 = 0.01998 0.00170 0.00547 0.00091 N2 6 0.627306 0.419074 0.322829 11.00000 0.02117 0.02013 = 0.01689 0.00087 0.00323 -0.00134 C3 1 0.227498 0.297443 0.360706 11.00000 0.02088 0.02509 = 0.02223 0.00226 0.00845 0.00027 AFIX 43 H3 2 0.149751 0.274550 0.364964 11.00000 -1.20000 AFIX 0 N3 6 0.593461 0.399459 0.218046 11.00000 0.02069 0.02057 = 0.01809 0.00129 0.00531 -0.00132 C4 1 0.312367 0.332443 0.396461 11.00000 0.02607 0.03019 = 0.01868 0.00344 0.00812 -0.00046 N4 6 0.355106 0.313213 0.218843 11.00000 0.01861 0.02228 = 0.01612 -0.00063 0.00248 -0.00127 C5 1 0.414832 0.357937 0.372072 11.00000 0.02257 0.03027 = 0.01442 0.00221 0.00362 0.00104 N5 6 0.095058 0.230005 0.276598 11.00000 0.01721 0.01979 = 0.02820 -0.00185 0.00484 -0.00048 C6 1 0.524816 0.395876 0.394072 11.00000 0.02514 0.03217 = 0.01443 -0.00084 0.00369 -0.00220 AFIX 43 H6 2 0.535069 0.402946 0.428543 11.00000 -1.20000 AFIX 0 C7 1 0.621750 0.424724 0.371360 11.00000 0.01966 0.02543 = 0.01968 -0.00179 0.00070 0.00000 C8 1 0.728411 0.469736 0.396287 11.00000 0.02247 0.03355 = 0.02340 -0.00809 -0.00012 -0.00150 AFIX 43 H8 2 0.746055 0.481128 0.430394 11.00000 -1.20000 AFIX 0 C9 1 0.799275 0.493059 0.362820 11.00000 0.01950 0.02634 = 0.02834 -0.00684 0.00232 0.00069 C10 1 0.733776 0.460224 0.316037 11.00000 0.01765 0.01804 = 0.02431 -0.00032 0.00144 -0.00037 C11 1 0.769421 0.468801 0.270241 11.00000 0.01917 0.02092 = 0.02797 0.00320 0.00635 -0.00031 AFIX 43 H11 2 0.845817 0.497116 0.269365 11.00000 -1.20000 AFIX 0 C12 1 0.705244 0.440403 0.225809 11.00000 0.02341 0.02020 = 0.02418 0.00567 0.00888 0.00063 C13 1 0.747843 0.452893 0.179913 11.00000 0.02708 0.02519 = 0.02691 0.00713 0.01174 0.00011 AFIX 43 H13 2 0.823428 0.479345 0.175633 11.00000 -1.20000 AFIX 0 C14 1 0.662165 0.420634 0.143871 11.00000 0.03255 0.02655 = 0.02399 0.00445 0.01371 0.00056 C15 1 0.563945 0.387016 0.168418 11.00000 0.02969 0.02145 = 0.01675 0.00177 0.00932 0.00024 C16 1 0.454639 0.348034 0.147116 11.00000 0.03185 0.02680 = 0.01450 -0.00019 0.00439 0.00041 AFIX 43 H16 2 0.441098 0.344652 0.112440 11.00000 -1.20000 AFIX 0 C17 1 0.362114 0.313172 0.170330 11.00000 0.02648 0.02306 = 0.01586 0.00009 0.00160 0.00151 C18 1 0.260347 0.266195 0.143907 11.00000 0.03168 0.03069 = 0.01757 -0.00344 -0.00190 0.00013 AFIX 43 H18 2 0.244576 0.258543 0.109450 11.00000 -1.20000 AFIX 0 C19 1 0.189687 0.234193 0.175789 11.00000 0.02116 0.02802 = 0.02259 -0.00359 -0.00275 -0.00085 C20 1 0.248761 0.268928 0.223937 11.00000 0.01696 0.02067 = 0.02056 -0.00160 -0.00014 0.00074 C21 1 0.092139 0.149345 0.296804 11.00000 0.02496 0.02057 = 0.02672 -0.00070 0.00606 0.00026 AFIX 43 H21 2 0.165059 0.115180 0.303032 11.00000 -1.20000 AFIX 0 C22 1 -0.015655 0.116744 0.308323 11.00000 0.03157 0.02427 = 0.03842 -0.00184 0.01236 -0.00623 AFIX 43 H22 2 -0.017756 0.060337 0.322706 11.00000 -1.20000 AFIX 0 C23 1 -0.121650 0.167233 0.298694 11.00000 0.02546 0.03511 = 0.05883 -0.00958 0.01576 -0.00746 AFIX 43 H23 2 -0.197412 0.145177 0.305828 11.00000 -1.20000 AFIX 0 C24 1 -0.116075 0.249374 0.278760 11.00000 0.01930 0.03361 = 0.07514 -0.00239 0.01422 0.00347 AFIX 43 H24 2 -0.187896 0.284677 0.272429 11.00000 -1.20000 AFIX 0 C25 1 -0.005768 0.280509 0.267942 11.00000 0.02212 0.02412 = 0.05145 0.00221 0.00658 0.00233 AFIX 43 H25 2 -0.001367 0.337446 0.254431 11.00000 -1.20000 AFIX 0 C26 1 0.302703 0.339906 0.450431 11.00000 0.03688 0.04499 = 0.01752 0.00000 0.01077 -0.00223 C27 1 0.314088 0.436284 0.467192 11.00000 0.05241 0.05701 = 0.02730 -0.01432 0.02134 -0.01295 AFIX 137 H27A 2 0.394549 0.459220 0.462651 11.00000 -1.50000 H27B 2 0.305907 0.439910 0.501824 11.00000 -1.50000 H27C 2 0.249051 0.471030 0.447763 11.00000 -1.50000 AFIX 0 C28 1 0.400630 0.282934 0.481232 11.00000 0.04694 0.07058 = 0.02040 0.01351 0.00383 -0.00435 AFIX 137 H28A 2 0.392095 0.222125 0.469762 11.00000 -1.50000 H28B 2 0.389782 0.285533 0.515610 11.00000 -1.50000 H28C 2 0.482588 0.304740 0.478006 11.00000 -1.50000 AFIX 0 C29 1 0.175211 0.306520 0.458311 11.00000 0.04709 0.05360 = 0.02457 0.00289 0.01971 -0.00734 AFIX 137 H29A 2 0.111002 0.340725 0.438051 11.00000 -1.50000 H29B 2 0.167018 0.313093 0.492812 11.00000 -1.50000 H29C 2 0.166621 0.244534 0.449077 11.00000 -1.50000 AFIX 0 C30 1 0.918909 0.543114 0.371001 11.00000 0.02206 0.04482 = 0.04214 -0.01949 0.00683 -0.01308 C31 1 0.906021 0.629984 0.343137 11.00000 0.04622 0.03675 = 0.08548 -0.01711 0.02483 -0.02004 AFIX 137 H31A 2 0.880977 0.618500 0.308164 11.00000 -1.50000 H31B 2 0.985076 0.660805 0.348331 11.00000 -1.50000 H31C 2 0.843748 0.666340 0.355052 11.00000 -1.50000 AFIX 0 C32 1 1.022980 0.487490 0.355382 11.00000 0.02101 0.07203 = 0.03751 -0.01393 0.00329 0.00038 AFIX 137 H32A 2 1.023445 0.429233 0.370329 11.00000 -1.50000 H32B 2 1.102177 0.516294 0.366190 11.00000 -1.50000 H32C 2 1.009398 0.481625 0.319709 11.00000 -1.50000 AFIX 0 C33 1 0.955045 0.562044 0.426085 11.00000 0.03335 0.10133 = 0.05687 -0.04842 0.00885 -0.02877 AFIX 137 H33A 2 0.892615 0.599598 0.437022 11.00000 -1.50000 H33B 2 1.034836 0.591853 0.431960 11.00000 -1.50000 H33C 2 0.960653 0.506712 0.444286 11.00000 -1.50000 AFIX 0 C34 1 0.670336 0.421338 0.089752 11.00000 0.04599 0.05237 = 0.02209 0.00263 0.01493 -0.01121 C35 1 0.665941 0.327664 0.069410 11.00000 0.09551 0.07834 = 0.04628 -0.02974 0.04425 -0.02886 AFIX 137 H35A 2 0.734381 0.293609 0.087114 11.00000 -1.50000 H35B 2 0.672701 0.329436 0.034598 11.00000 -1.50000 H35C 2 0.587931 0.300095 0.073521 11.00000 -1.50000 AFIX 0 C36 1 0.570396 0.477645 0.062238 11.00000 0.07255 0.09215 = 0.03325 0.02526 0.00684 -0.01204 AFIX 137 H36A 2 0.578253 0.537579 0.075112 11.00000 -1.50000 H36B 2 0.489988 0.453839 0.066195 11.00000 -1.50000 H36C 2 0.577827 0.478209 0.027477 11.00000 -1.50000 AFIX 0 C37 1 0.795441 0.462092 0.082900 11.00000 0.06815 0.08799 = 0.03575 -0.00195 0.02807 -0.02842 AFIX 137 H37A 2 0.862575 0.425406 0.099380 11.00000 -1.50000 H37B 2 0.802427 0.521128 0.097035 11.00000 -1.50000 H37C 2 0.800336 0.465483 0.047957 11.00000 -1.50000 AFIX 0 C38 1 0.088113 0.166631 0.159419 11.00000 0.04454 0.06873 = 0.03793 -0.02470 0.00859 -0.02933 C39 1 0.137101 0.074361 0.187227 11.00000 0.06881 0.05236 = 0.05481 -0.00901 0.00792 -0.01301 AFIX 137 H39A 2 0.145503 0.082323 0.222694 11.00000 -1.50000 H39B 2 0.217049 0.058602 0.178535 11.00000 -1.50000 H39C 2 0.077795 0.027451 0.176939 11.00000 -1.50000 AFIX 0 C40 1 -0.036501 0.182528 0.169672 11.00000 0.04177 0.09999 = 0.09136 -0.02513 -0.00460 -0.01288 AFIX 137 H40A 2 -0.063802 0.241017 0.157947 11.00000 -1.50000 H40B 2 -0.036388 0.178914 0.204980 11.00000 -1.50000 H40C 2 -0.092579 0.138274 0.152937 11.00000 -1.50000 AFIX 0 C41 1 0.086126 0.143159 0.105741 11.00000 0.05673 0.05599 = 0.02877 -0.00731 -0.00659 -0.02494 AFIX 137 H41A 2 0.065946 0.195462 0.085500 11.00000 -1.50000 H41B 2 0.024040 0.097781 0.096023 11.00000 -1.50000 H41C 2 0.167118 0.121168 0.101251 11.00000 -1.50000 AFIX 6 PART 1 B2 3 0.083701 0.528830 0.204090 10.67000 0.04557 0.03896 = 0.05538 -0.00101 0.02662 -0.01358 F3 5 0.203931 0.517635 0.194639 10.67000 0.04136 0.12422 = 0.05824 -0.01024 0.01666 -0.03841 F4 5 0.007858 0.557632 0.161471 10.67000 0.05704 0.27620 = 0.04503 0.04199 -0.00115 -0.05958 F5 5 0.039485 0.448847 0.219048 10.67000 0.06413 0.05128 = 0.21527 0.05462 0.07303 -0.00006 F6 5 0.083439 0.591376 0.241171 10.67000 0.09731 0.05689 = 0.15174 -0.03693 -0.05294 0.03363 AFIX 0 PART 0 PART 2 B2A 3 0.108062 0.514509 0.213008 10.33000 0.02904 0.05136 = 0.07779 0.02965 0.01333 -0.01100 F3A 5 0.217676 0.504660 0.249369 10.33000 0.06336 0.08438 = 0.09897 0.00588 -0.01522 0.01336 F4A 5 0.134430 0.569993 0.177832 10.33000 0.06349 0.07467 = 0.04971 -0.00857 0.02791 -0.02598 F5A 5 0.052930 0.445103 0.194354 10.33000 0.04469 0.03384 = 0.06852 0.01075 0.03496 -0.01615 F6A 5 0.030156 0.561863 0.239721 10.33000 0.05320 0.03088 = 0.02387 -0.01001 0.02058 -0.01494 PART 0 PART 1 CL3 4 0.787988 0.300709 0.500546 11.00000 0.13776 0.08587 = 0.05461 -0.01460 -0.00113 -0.03166 CL4 4 0.846764 0.240913 0.407596 11.00000 0.13125 0.09313 = 0.11505 0.00429 0.08206 0.01468 C44 1 0.770535 0.220504 0.456542 11.00000 0.14607 0.09832 = 0.06708 -0.02016 0.05841 -0.02225 AFIX 23 H44A 2 0.681789 0.213412 0.443967 11.00000 -1.20000 H44B 2 0.800781 0.164350 0.471899 11.00000 -1.20000 AFIX 0 PART 0 CL1 4 0.247476 1.051812 0.426171 11.00000 0.08704 0.11227 = 0.06454 -0.01234 0.01741 0.04404 CL2 4 0.396545 0.902040 0.466280 11.00000 0.13714 0.05721 = 0.05532 0.00674 0.01963 -0.00221 C42 1 0.360520 0.976317 0.418551 11.00000 0.08521 0.05031 = 0.05604 0.01181 0.03074 0.00952 AFIX 23 H42A 2 0.436123 1.008605 0.414448 11.00000 -1.20000 H42B 2 0.333260 0.943150 0.388028 11.00000 -1.20000 AFIX 0 O2 7 0.543808 0.173147 0.381635 10.63000 0.08600 0.06077 = 0.04849 0.00955 0.00818 0.02867 HKLF 4 REM 1905cd85_0m_a.res in P2(1)/n REM wR2 = 0.2184, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0765 for 8936 Fo > 4sig(Fo) and 0.0894 for all 10589 data REM 590 parameters refined using 0 restraints END WGHT 0.1171 17.3008 REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, y-1/2, -z+1/2 HTAB O1 F6_$1 HTAB O1 F6A_$1 HTAB O1 F4_$1 HTAB O1 O2 EQIV $2 x+1, y, z HTAB C11 F6A_$2 HTAB C13 F4_$2 HTAB C13 F5_$2 HTAB C13 F5A_$2 HTAB C21 F3_$1 HTAB C21 F4A_$1 HTAB C25 F5 HTAB C25 F5A HTAB C44 O2 EQIV $3 -x+1/2, y+1/2, -z+1/2 HTAB C42 F4_$3 HTAB C42 F3_$3 REM Highest difference peak 3.526, deepest hole -1.742, 1-sigma level 0.121 Q1 1 0.2992 0.9023 0.4681 11.00000 0.05 3.53 Q2 1 0.6952 0.1937 0.4076 11.00000 0.05 2.44 Q3 1 0.0373 0.1140 0.1864 11.00000 0.05 2.33 Q4 1 -0.0375 0.2499 0.1394 11.00000 0.05 2.19 Q5 1 -0.0007 0.5825 0.1673 11.00000 0.05 1.52 Q6 1 0.8629 0.2631 0.5078 11.00000 0.05 1.15 Q7 1 0.9006 0.1947 0.4483 11.00000 0.05 1.08 Q8 1 0.5601 0.3670 0.0498 11.00000 0.05 0.91 Q9 1 0.8365 0.3025 0.4767 11.00000 0.05 0.89 Q10 1 0.7875 0.3611 0.0803 11.00000 0.05 0.80 Q11 1 0.6725 0.5112 0.0687 11.00000 0.05 0.74 Q12 1 0.1008 0.5938 0.2184 11.00000 0.05 0.70 Q13 1 0.0196 0.5081 0.1619 11.00000 0.05 0.59 Q14 1 0.8096 0.2754 0.4347 11.00000 0.05 0.56 Q15 1 0.5662 0.4145 0.3786 11.00000 0.05 0.44 Q16 1 0.7819 0.4833 0.3397 11.00000 0.05 0.44 Q17 1 0.1809 0.5178 0.2018 11.00000 0.05 0.44 Q18 1 0.2928 1.0800 0.4105 11.00000 0.05 0.44 Q19 1 0.2667 0.4882 0.2059 11.00000 0.05 0.42 Q20 1 0.0613 0.4664 0.2270 11.00000 0.05 0.41 ; _shelx_res_checksum 6303 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5841(2) 0.22407(18) 0.28456(11) 0.0278(6) Uani 1 1 d . . . . H1A H 0.534285 0.178217 0.268959 0.042 Uiso 1 1 d GR . . . H1B H 0.592596 0.205907 0.317669 0.042 Uiso 1 1 d GR . . . Zn Zn 0.50073(3) 0.35394(3) 0.27137(2) 0.01650(13) Uani 1 1 d . . . . C1 C 0.2141(3) 0.2674(2) 0.27037(13) 0.0192(6) Uani 1 1 d . . . . N1 N 0.3881(3) 0.3387(2) 0.32296(10) 0.0200(6) Uani 1 1 d . . . . C2 C 0.2750(3) 0.3008(2) 0.31517(12) 0.0194(6) Uani 1 1 d . . . . N2 N 0.6273(3) 0.41907(19) 0.32283(10) 0.0194(6) Uani 1 1 d . . . . C3 C 0.2275(3) 0.2974(2) 0.36071(13) 0.0222(7) Uani 1 1 d . . . . H3 H 0.149751 0.274550 0.364964 0.027 Uiso 1 1 calc R . . . N3 N 0.5935(3) 0.39946(19) 0.21805(10) 0.0195(6) Uani 1 1 d . . . . C4 C 0.3124(3) 0.3324(3) 0.39646(13) 0.0245(7) Uani 1 1 d . . . . N4 N 0.3551(3) 0.3132(2) 0.21884(10) 0.0190(6) Uani 1 1 d . . . . C5 C 0.4148(3) 0.3579(2) 0.37207(12) 0.0223(7) Uani 1 1 d . . . . N5 N 0.0951(3) 0.2300(2) 0.27660(11) 0.0216(6) Uani 1 1 d . . . . C6 C 0.5248(3) 0.3959(3) 0.39407(12) 0.0239(7) Uani 1 1 d . . . . H6 H 0.535069 0.402946 0.428543 0.029 Uiso 1 1 calc R . . . C7 C 0.6217(3) 0.4247(2) 0.37136(13) 0.0219(7) Uani 1 1 d . . . . C8 C 0.7284(3) 0.4697(3) 0.39629(14) 0.0269(8) Uani 1 1 d . . . . H8 H 0.746055 0.481128 0.430394 0.032 Uiso 1 1 calc R . . . C9 C 0.7993(3) 0.4931(3) 0.36282(14) 0.0249(7) Uani 1 1 d . . . . C10 C 0.7338(3) 0.4602(2) 0.31604(13) 0.0202(7) Uani 1 1 d . . . . C11 C 0.7694(3) 0.4688(2) 0.27024(13) 0.0224(7) Uani 1 1 d . . . . H11 H 0.845817 0.497116 0.269365 0.027 Uiso 1 1 calc R . . . C12 C 0.7052(3) 0.4404(2) 0.22581(13) 0.0220(7) Uani 1 1 d . . . . C13 C 0.7478(4) 0.4529(2) 0.17991(14) 0.0256(7) Uani 1 1 d . . . . H13 H 0.823428 0.479345 0.175633 0.031 Uiso 1 1 calc R . . . C14 C 0.6622(4) 0.4206(3) 0.14387(14) 0.0267(8) Uani 1 1 d . . . . C15 C 0.5639(3) 0.3870(2) 0.16842(12) 0.0220(7) Uani 1 1 d . . . . C16 C 0.4546(4) 0.3480(2) 0.14712(13) 0.0243(7) Uani 1 1 d . . . . H16 H 0.441098 0.344652 0.112440 0.029 Uiso 1 1 calc R . . . C17 C 0.3621(3) 0.3132(2) 0.17033(12) 0.0220(7) Uani 1 1 d . . . . C18 C 0.2603(4) 0.2662(3) 0.14391(13) 0.0273(8) Uani 1 1 d . . . . H18 H 0.244576 0.258543 0.109450 0.033 Uiso 1 1 calc R . . . C19 C 0.1897(3) 0.2342(3) 0.17579(13) 0.0246(7) Uani 1 1 d . . . . C20 C 0.2488(3) 0.2689(2) 0.22394(12) 0.0197(7) Uani 1 1 d . . . . C21 C 0.0921(3) 0.1493(2) 0.29680(14) 0.0239(7) Uani 1 1 d . . . . H21 H 0.165059 0.115180 0.303032 0.029 Uiso 1 1 calc R . . . C22 C -0.0157(4) 0.1167(3) 0.30832(16) 0.0307(8) Uani 1 1 d . . . . H22 H -0.017756 0.060337 0.322706 0.037 Uiso 1 1 calc R . . . C23 C -0.1216(4) 0.1672(3) 0.29869(19) 0.0388(10) Uani 1 1 d . . . . H23 H -0.197412 0.145177 0.305828 0.047 Uiso 1 1 calc R . . . C24 C -0.1161(4) 0.2494(3) 0.2788(2) 0.0420(11) Uani 1 1 d . . . . H24 H -0.187896 0.284677 0.272429 0.050 Uiso 1 1 calc R . . . C25 C -0.0058(3) 0.2805(3) 0.26794(17) 0.0325(9) Uani 1 1 d . . . . H25 H -0.001367 0.337446 0.254431 0.039 Uiso 1 1 calc R . . . C26 C 0.3027(4) 0.3399(3) 0.45043(14) 0.0324(9) Uani 1 1 d . . . . C27 C 0.3141(5) 0.4363(4) 0.46719(16) 0.0439(12) Uani 1 1 d . . . . H27A H 0.394549 0.459220 0.462651 0.066 Uiso 1 1 calc GR . . . H27B H 0.305907 0.439910 0.501824 0.066 Uiso 1 1 calc GR . . . H27C H 0.249051 0.471030 0.447763 0.066 Uiso 1 1 calc GR . . . C28 C 0.4006(5) 0.2829(4) 0.48123(16) 0.0461(12) Uani 1 1 d . . . . H28A H 0.392095 0.222125 0.469762 0.069 Uiso 1 1 calc GR . . . H28B H 0.389782 0.285533 0.515610 0.069 Uiso 1 1 calc GR . . . H28C H 0.482588 0.304740 0.478006 0.069 Uiso 1 1 calc GR . . . C29 C 0.1752(5) 0.3065(3) 0.45831(16) 0.0402(10) Uani 1 1 d . . . . H29A H 0.111002 0.340725 0.438051 0.060 Uiso 1 1 calc GR . . . H29B H 0.167018 0.313093 0.492812 0.060 Uiso 1 1 calc GR . . . H29C H 0.166621 0.244534 0.449077 0.060 Uiso 1 1 calc GR . . . C30 C 0.9189(4) 0.5431(3) 0.37100(17) 0.0362(10) Uani 1 1 d . . . . C31 C 0.9060(5) 0.6300(3) 0.3431(2) 0.0546(15) Uani 1 1 d . . . . H31A H 0.880977 0.618500 0.308164 0.082 Uiso 1 1 calc GR . . . H31B H 0.985076 0.660805 0.348331 0.082 Uiso 1 1 calc GR . . . H31C H 0.843748 0.666340 0.355052 0.082 Uiso 1 1 calc GR . . . C32 C 1.0230(4) 0.4875(4) 0.35538(17) 0.0437(12) Uani 1 1 d . . . . H32A H 1.023445 0.429233 0.370329 0.066 Uiso 1 1 calc GR . . . H32B H 1.102177 0.516294 0.366190 0.066 Uiso 1 1 calc GR . . . H32C H 1.009398 0.481625 0.319709 0.066 Uiso 1 1 calc GR . . . C33 C 0.9550(5) 0.5620(5) 0.4261(2) 0.0637(19) Uani 1 1 d . . . . H33A H 0.892615 0.599598 0.437022 0.096 Uiso 1 1 calc GR . . . H33B H 1.034836 0.591853 0.431960 0.096 Uiso 1 1 calc GR . . . H33C H 0.960653 0.506712 0.444286 0.096 Uiso 1 1 calc GR . . . C34 C 0.6703(5) 0.4213(3) 0.08975(15) 0.0391(10) Uani 1 1 d . . . . C35 C 0.6659(7) 0.3277(5) 0.0694(2) 0.070(2) Uani 1 1 d . . . . H35A H 0.734381 0.293609 0.087114 0.105 Uiso 1 1 calc GR . . . H35B H 0.672701 0.329436 0.034598 0.105 Uiso 1 1 calc GR . . . H35C H 0.587931 0.300095 0.073521 0.105 Uiso 1 1 calc GR . . . C36 C 0.5704(6) 0.4776(5) 0.0622(2) 0.0662(18) Uani 1 1 d . . . . H36A H 0.578253 0.537579 0.075112 0.099 Uiso 1 1 calc GR . . . H36B H 0.489988 0.453839 0.066195 0.099 Uiso 1 1 calc GR . . . H36C H 0.577827 0.478209 0.027477 0.099 Uiso 1 1 calc GR . . . C37 C 0.7954(6) 0.4621(5) 0.0829(2) 0.0618(17) Uani 1 1 d . . . . H37A H 0.862575 0.425406 0.099380 0.093 Uiso 1 1 calc GR . . . H37B H 0.802427 0.521128 0.097035 0.093 Uiso 1 1 calc GR . . . H37C H 0.800336 0.465483 0.047957 0.093 Uiso 1 1 calc GR . . . C38 C 0.0881(5) 0.1666(4) 0.15942(19) 0.0502(14) Uani 1 1 d . . . . C39 C 0.1371(6) 0.0744(4) 0.1872(2) 0.0589(15) Uani 1 1 d . . . . H39A H 0.145503 0.082323 0.222694 0.088 Uiso 1 1 calc GR . . . H39B H 0.217049 0.058602 0.178535 0.088 Uiso 1 1 calc GR . . . H39C H 0.077795 0.027451 0.176939 0.088 Uiso 1 1 calc GR . . . C40 C -0.0365(6) 0.1825(6) 0.1697(3) 0.079(2) Uani 1 1 d . . . . H40A H -0.063802 0.241017 0.157947 0.119 Uiso 1 1 calc GR . . . H40B H -0.036388 0.178914 0.204980 0.119 Uiso 1 1 calc GR . . . H40C H -0.092579 0.138274 0.152937 0.119 Uiso 1 1 calc GR . . . C41 C 0.0861(5) 0.1432(4) 0.10574(17) 0.0486(13) Uani 1 1 d . . . . H41A H 0.065946 0.195462 0.085500 0.073 Uiso 1 1 calc GR . . . H41B H 0.024040 0.097781 0.096023 0.073 Uiso 1 1 calc GR . . . H41C H 0.167118 0.121168 0.101251 0.073 Uiso 1 1 calc GR . . . B2 B 0.0837(3) 0.5288(3) 0.20409(13) 0.045(4) Uani 0.67 1 d . P A 1 F3 F 0.2039(3) 0.5176(4) 0.19464(18) 0.0737(18) Uani 0.67 1 d G P A 1 F4 F 0.0079(4) 0.5576(5) 0.16147(15) 0.127(4) Uani 0.67 1 d G P A 1 F5 F 0.0395(5) 0.4488(3) 0.2190(3) 0.105(4) Uani 0.67 1 d G P A 1 F6 F 0.0834(6) 0.5914(4) 0.24117(19) 0.110(3) Uani 0.67 1 d G P A 1 B2A B 0.108(3) 0.515(2) 0.2130(13) 0.052(6) Uani 0.33 1 d . P B 2 F3A F 0.2177(11) 0.5047(9) 0.2494(5) 0.085(4) Uani 0.33 1 d . P B 2 F4A F 0.1344(11) 0.5700(8) 0.1778(4) 0.061(3) Uani 0.33 1 d . P B 2 F5A F 0.0529(10) 0.4451(7) 0.1944(4) 0.046(2) Uani 0.33 1 d . P B 2 F6A F 0.0302(9) 0.5619(6) 0.2397(3) 0.0344(19) Uani 0.33 1 d . P B 2 Cl3 Cl 0.7880(2) 0.30071(15) 0.50055(7) 0.0946(7) Uani 1 1 d . . C 1 Cl4 Cl 0.8468(3) 0.24091(16) 0.40760(10) 0.1063(8) Uani 1 1 d . . C 1 C44 C 0.7705(10) 0.2205(6) 0.4565(3) 0.099(3) Uani 1 1 d . . C 1 H44A H 0.681789 0.213412 0.443967 0.119 Uiso 1 1 calc R . C 1 H44B H 0.800781 0.164350 0.471899 0.119 Uiso 1 1 calc R . C 1 Cl1 Cl 0.24748(19) 1.05181(16) 0.42617(7) 0.0874(6) Uani 1 1 d . . . . Cl2 Cl 0.3965(2) 0.90204(12) 0.46628(6) 0.0828(6) Uani 1 1 d . . . . C42 C 0.3605(7) 0.9763(4) 0.4186(2) 0.0617(16) Uani 1 1 d . . . . H42A H 0.436123 1.008605 0.414448 0.074 Uiso 1 1 calc R . . . H42B H 0.333260 0.943150 0.388028 0.074 Uiso 1 1 calc R . . . O2 O 0.5438(7) 0.1731(5) 0.3816(2) 0.0654(19) Uani 0.63 1 d . P . . 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 0.0210(12) 0.0283(14) 0.0351(14) 0.0049(11) 0.0073(11) 0.0025(10) Zn 0.0159(2) 0.0200(2) 0.0139(2) 0.00022(13) 0.00354(14) -0.00173(14) C1 0.0148(15) 0.0205(16) 0.0219(16) -0.0001(13) 0.0019(12) 0.0000(12) N1 0.0175(13) 0.0272(15) 0.0157(13) -0.0006(11) 0.0035(10) -0.0023(11) C2 0.0178(15) 0.0213(16) 0.0200(16) 0.0017(12) 0.0055(12) 0.0009(12) N2 0.0212(14) 0.0201(14) 0.0169(13) 0.0009(11) 0.0032(10) -0.0013(11) C3 0.0209(16) 0.0251(17) 0.0222(16) 0.0023(13) 0.0084(13) 0.0003(13) N3 0.0207(14) 0.0206(14) 0.0181(13) 0.0013(11) 0.0053(11) -0.0013(11) C4 0.0261(18) 0.0302(18) 0.0187(16) 0.0034(14) 0.0081(13) -0.0005(14) N4 0.0186(13) 0.0223(14) 0.0161(13) -0.0006(11) 0.0025(10) -0.0013(11) C5 0.0226(17) 0.0303(18) 0.0144(15) 0.0022(13) 0.0036(13) 0.0010(14) N5 0.0172(14) 0.0198(14) 0.0282(15) -0.0018(12) 0.0048(11) -0.0005(11) C6 0.0251(17) 0.0322(19) 0.0144(15) -0.0008(13) 0.0037(13) -0.0022(15) C7 0.0197(16) 0.0254(17) 0.0197(16) -0.0018(13) 0.0007(13) 0.0000(13) C8 0.0225(17) 0.034(2) 0.0234(17) -0.0081(15) -0.0001(14) -0.0015(15) C9 0.0195(16) 0.0263(18) 0.0283(18) -0.0068(14) 0.0023(14) 0.0007(14) C10 0.0177(15) 0.0180(15) 0.0243(17) -0.0003(13) 0.0014(13) -0.0004(12) C11 0.0192(16) 0.0209(16) 0.0280(17) 0.0032(13) 0.0063(13) -0.0003(13) C12 0.0234(17) 0.0202(16) 0.0242(17) 0.0057(13) 0.0089(13) 0.0006(13) C13 0.0271(18) 0.0252(18) 0.0269(18) 0.0071(14) 0.0117(14) 0.0001(14) C14 0.0325(19) 0.0265(18) 0.0240(18) 0.0045(14) 0.0137(15) 0.0006(15) C15 0.0297(18) 0.0214(16) 0.0167(15) 0.0018(13) 0.0093(13) 0.0002(14) C16 0.0319(19) 0.0268(18) 0.0145(15) -0.0002(13) 0.0044(13) 0.0004(14) C17 0.0265(17) 0.0231(17) 0.0159(15) 0.0001(13) 0.0016(13) 0.0015(14) C18 0.0317(19) 0.0307(19) 0.0176(16) -0.0034(14) -0.0019(14) 0.0001(15) C19 0.0212(17) 0.0280(18) 0.0226(17) -0.0036(14) -0.0028(13) -0.0008(14) C20 0.0170(15) 0.0207(16) 0.0206(16) -0.0016(12) -0.0001(12) 0.0007(12) C21 0.0250(17) 0.0206(17) 0.0267(18) -0.0007(13) 0.0061(14) 0.0003(13) C22 0.032(2) 0.0243(18) 0.038(2) -0.0018(16) 0.0124(17) -0.0062(16) C23 0.025(2) 0.035(2) 0.059(3) -0.010(2) 0.0158(19) -0.0075(17) C24 0.0193(18) 0.034(2) 0.075(3) -0.002(2) 0.014(2) 0.0035(16) C25 0.0221(18) 0.0241(19) 0.051(3) 0.0022(17) 0.0066(17) 0.0023(14) C26 0.037(2) 0.045(2) 0.0175(17) 0.0000(16) 0.0108(15) -0.0022(18) C27 0.052(3) 0.057(3) 0.027(2) -0.014(2) 0.0213(19) -0.013(2) C28 0.047(3) 0.071(3) 0.0204(19) 0.014(2) 0.0038(18) -0.004(2) C29 0.047(3) 0.054(3) 0.0246(19) 0.0029(18) 0.0197(18) -0.007(2) C30 0.0221(18) 0.045(2) 0.042(2) -0.0195(19) 0.0068(16) -0.0131(17) C31 0.046(3) 0.037(3) 0.085(4) -0.017(3) 0.025(3) -0.020(2) C32 0.0210(19) 0.072(3) 0.038(2) -0.014(2) 0.0033(17) 0.000(2) C33 0.033(2) 0.101(5) 0.057(3) -0.048(3) 0.009(2) -0.029(3) C34 0.046(3) 0.052(3) 0.0221(19) 0.0026(18) 0.0149(17) -0.011(2) C35 0.096(5) 0.078(4) 0.046(3) -0.030(3) 0.044(3) -0.029(4) C36 0.073(4) 0.092(5) 0.033(3) 0.025(3) 0.007(3) -0.012(4) C37 0.068(4) 0.088(5) 0.036(3) -0.002(3) 0.028(3) -0.028(3) C38 0.045(3) 0.069(3) 0.038(2) -0.025(2) 0.009(2) -0.029(3) C39 0.069(4) 0.052(3) 0.055(3) -0.009(3) 0.008(3) -0.013(3) C40 0.042(3) 0.100(6) 0.091(5) -0.025(5) -0.005(3) -0.013(3) C41 0.057(3) 0.056(3) 0.029(2) -0.007(2) -0.007(2) -0.025(2) B2 0.046(8) 0.039(6) 0.055(7) -0.001(6) 0.027(6) -0.014(5) F3 0.041(3) 0.124(6) 0.058(3) -0.010(3) 0.017(2) -0.038(3) F4 0.057(3) 0.276(12) 0.045(3) 0.042(5) -0.001(3) -0.060(5) F5 0.064(4) 0.051(4) 0.215(11) 0.055(6) 0.073(6) 0.000(3) F6 0.097(6) 0.057(4) 0.152(8) -0.037(4) -0.053(5) 0.034(4) B2A 0.029(8) 0.051(12) 0.078(15) 0.030(12) 0.013(10) -0.011(10) F3A 0.063(7) 0.084(9) 0.099(10) 0.006(7) -0.015(7) 0.013(6) F4A 0.063(7) 0.075(7) 0.050(6) -0.009(5) 0.028(5) -0.026(6) F5A 0.045(5) 0.034(5) 0.069(6) 0.011(4) 0.035(5) -0.016(4) F6A 0.053(5) 0.031(4) 0.024(3) -0.010(3) 0.021(4) -0.015(4) Cl3 0.1378(19) 0.0859(13) 0.0546(10) -0.0146(9) -0.0011(11) -0.0317(13) Cl4 0.131(2) 0.0931(15) 0.1151(18) 0.0043(13) 0.0821(16) 0.0147(14) C44 0.146(8) 0.098(6) 0.067(5) -0.020(4) 0.058(5) -0.022(6) Cl1 0.0870(13) 0.1123(16) 0.0645(10) -0.0123(10) 0.0174(9) 0.0440(12) Cl2 0.1371(18) 0.0572(9) 0.0553(9) 0.0067(7) 0.0196(10) -0.0022(10) C42 0.085(4) 0.050(3) 0.056(3) 0.012(3) 0.031(3) 0.010(3) O2 0.086(5) 0.061(4) 0.048(4) 0.010(3) 0.008(3) 0.029(4) 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' Zn Zn 0.2839 1.4301 '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 H1A O1 H1B 100.7 Zn O1 H1A 113.2 Zn O1 H1B 113.5 N1 Zn O1 93.78(11) N1 Zn N2 89.45(11) N1 Zn N4 88.22(11) N2 Zn O1 95.76(11) N2 Zn N4 168.24(12) N3 Zn O1 100.50(11) N3 Zn N1 165.70(12) N3 Zn N2 88.60(11) N3 Zn N4 90.83(11) N4 Zn O1 95.89(11) C2 C1 N5 110.2(3) C20 C1 C2 130.0(3) C20 C1 N5 119.7(3) C2 N1 Zn 125.4(2) C2 N1 C5 107.0(3) C5 N1 Zn 127.4(2) C1 C2 C3 124.8(3) N1 C2 C1 126.0(3) N1 C2 C3 109.2(3) C7 N2 Zn 125.2(2) C7 N2 C10 106.4(3) C10 N2 Zn 128.3(2) C2 C3 H3 125.7 C4 C3 C2 108.7(3) C4 C3 H3 125.7 C12 N3 Zn 125.6(2) C12 N3 C15 106.4(3) C15 N3 Zn 127.6(2) C3 C4 C5 105.1(3) C3 C4 C26 126.7(3) C5 C4 C26 128.1(3) C17 N4 Zn 122.2(2) C17 N4 C20 106.6(3) C20 N4 Zn 130.3(2) N1 C5 C4 110.1(3) N1 C5 C6 123.6(3) C6 C5 C4 126.3(3) C21 N5 C1 118.9(3) C25 N5 C1 119.1(3) C25 N5 C21 121.4(3) C5 C6 H6 116.2 C5 C6 C7 127.5(3) C7 C6 H6 116.2 N2 C7 C6 125.9(3) N2 C7 C8 110.0(3) C6 C7 C8 124.0(3) C7 C8 H8 125.9 C9 C8 C7 108.3(3) C9 C8 H8 125.9 C8 C9 C10 105.1(3) C8 C9 C30 128.1(4) C10 C9 C30 126.8(3) N2 C10 C9 110.2(3) N2 C10 C11 122.8(3) C11 C10 C9 127.0(3) C10 C11 H11 116.5 C12 C11 C10 126.9(3) C12 C11 H11 116.5 N3 C12 C11 126.9(3) N3 C12 C13 109.6(3) C11 C12 C13 123.5(3) C12 C13 H13 125.8 C14 C13 C12 108.5(3) C14 C13 H13 125.8 C13 C14 C15 105.4(3) C13 C14 C34 125.6(4) C15 C14 C34 129.0(4) N3 C15 C14 110.1(3) N3 C15 C16 122.3(3) C16 C15 C14 127.6(3) C15 C16 H16 116.0 C15 C16 C17 128.0(3) C17 C16 H16 116.0 N4 C17 C16 128.2(3) N4 C17 C18 110.0(3) C16 C17 C18 121.7(3) C17 C18 H18 125.3 C19 C18 C17 109.3(3) C19 C18 H18 125.3 C18 C19 C20 104.0(3) C18 C19 C38 121.0(4) C20 C19 C38 134.3(4) C1 C20 C19 132.5(3) N4 C20 C1 117.6(3) N4 C20 C19 109.8(3) N5 C21 H21 119.9 N5 C21 C22 120.3(4) C22 C21 H21 119.9 C21 C22 H22 120.4 C21 C22 C23 119.2(4) C23 C22 H22 120.4 C22 C23 H23 120.3 C24 C23 C22 119.5(4) C24 C23 H23 120.3 C23 C24 H24 120.1 C23 C24 C25 119.9(4) C25 C24 H24 120.1 N5 C25 C24 119.7(4) N5 C25 H25 120.1 C24 C25 H25 120.1 C4 C26 C27 110.7(3) C4 C26 C28 110.5(4) C4 C26 C29 108.9(3) C27 C26 C29 107.7(4) C28 C26 C27 110.9(4) C28 C26 C29 108.0(4) C26 C27 H27A 109.5 C26 C27 H27B 109.5 C26 C27 H27C 109.5 H27A C27 H27B 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C26 C28 H28A 109.5 C26 C28 H28B 109.5 C26 C28 H28C 109.5 H28A C28 H28B 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C26 C29 H29A 109.5 C26 C29 H29B 109.5 C26 C29 H29C 109.5 H29A C29 H29B 109.5 H29A C29 H29C 109.5 H29B C29 H29C 109.5 C9 C30 C31 110.8(4) C9 C30 C32 110.5(4) C9 C30 C33 108.9(4) C31 C30 C32 110.3(4) C31 C30 C33 109.0(5) C33 C30 C32 107.2(4) C30 C31 H31A 109.5 C30 C31 H31B 109.5 C30 C31 H31C 109.5 H31A C31 H31B 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 C30 C32 H32A 109.5 C30 C32 H32B 109.5 C30 C32 H32C 109.5 H32A C32 H32B 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 C30 C33 H33A 109.5 C30 C33 H33B 109.5 C30 C33 H33C 109.5 H33A C33 H33B 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 C14 C34 C35 110.7(4) C14 C34 C37 108.6(4) C35 C34 C37 107.7(5) C36 C34 C14 110.5(4) C36 C34 C35 111.6(5) C36 C34 C37 107.6(5) C34 C35 H35A 109.5 C34 C35 H35B 109.5 C34 C35 H35C 109.5 H35A C35 H35B 109.5 H35A C35 H35C 109.5 H35B C35 H35C 109.5 C34 C36 H36A 109.5 C34 C36 H36B 109.5 C34 C36 H36C 109.5 H36A C36 H36B 109.5 H36A C36 H36C 109.5 H36B C36 H36C 109.5 C34 C37 H37A 109.5 C34 C37 H37B 109.5 C34 C37 H37C 109.5 H37A C37 H37B 109.5 H37A C37 H37C 109.5 H37B C37 H37C 109.5 C19 C38 C39 105.4(4) C40 C38 C19 119.5(5) C40 C38 C39 107.2(5) C40 C38 C41 111.1(5) C41 C38 C19 109.9(4) C41 C38 C39 102.0(5) C38 C39 H39A 109.5 C38 C39 H39B 109.5 C38 C39 H39C 109.5 H39A C39 H39B 109.5 H39A C39 H39C 109.5 H39B C39 H39C 109.5 C38 C40 H40A 109.5 C38 C40 H40B 109.5 C38 C40 H40C 109.5 H40A C40 H40B 109.5 H40A C40 H40C 109.5 H40B C40 H40C 109.5 C38 C41 H41A 109.5 C38 C41 H41B 109.5 C38 C41 H41C 109.5 H41A C41 H41B 109.5 H41A C41 H41C 109.5 H41B C41 H41C 109.5 F3 B2 F4 109.5 F3 B2 F6 109.5 F5 B2 F3 109.5 F5 B2 F4 109.5 F5 B2 F6 109.5 F6 B2 F4 109.4 F4A B2A F3A 108.2(17) F4A B2A F6A 106(2) F5A B2A F3A 119(3) F5A B2A F4A 111(3) F5A B2A F6A 110.0(18) F6A B2A F3A 101(2) Cl3 C44 Cl4 114.5(5) Cl3 C44 H44A 108.6 Cl3 C44 H44B 108.6 Cl4 C44 H44A 108.6 Cl4 C44 H44B 108.6 H44A C44 H44B 107.6 Cl1 C42 Cl2 114.9(3) Cl1 C42 H42A 108.5 Cl1 C42 H42B 108.5 Cl2 C42 H42A 108.5 Cl2 C42 H42B 108.5 H42A C42 H42B 107.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1A 0.9495 O1 H1B 0.9487 O1 Zn 2.189(3) Zn N1 2.052(3) Zn N2 2.080(3) Zn N3 2.049(3) Zn N4 2.081(3) C1 C2 1.408(5) C1 N5 1.466(4) C1 C20 1.400(5) N1 C2 1.360(4) N1 C5 1.377(4) C2 C3 1.443(5) N2 C7 1.359(4) N2 C10 1.370(4) C3 H3 0.9500 C3 C4 1.358(5) N3 C12 1.367(5) N3 C15 1.375(4) C4 C5 1.459(5) C4 C26 1.521(5) N4 C17 1.359(4) N4 C20 1.379(4) C5 C6 1.392(5) N5 C21 1.354(5) N5 C25 1.342(5) C6 H6 0.9500 C6 C7 1.395(5) C7 C8 1.438(5) C8 H8 0.9500 C8 C9 1.353(6) C9 C10 1.467(5) C9 C30 1.509(5) C10 C11 1.394(5) C11 H11 0.9500 C11 C12 1.387(5) C12 C13 1.438(5) C13 H13 0.9500 C13 C14 1.352(6) C14 C15 1.461(5) C14 C34 1.517(5) C15 C16 1.387(5) C16 H16 0.9500 C16 C17 1.396(5) C17 C18 1.429(5) C18 H18 0.9500 C18 C19 1.359(6) C19 C20 1.485(5) C19 C38 1.535(6) C21 H21 0.9500 C21 C22 1.372(5) C22 H22 0.9500 C22 C23 1.389(6) C23 H23 0.9500 C23 C24 1.375(7) C24 H24 0.9500 C24 C25 1.382(6) C25 H25 0.9500 C26 C27 1.541(7) C26 C28 1.534(7) C26 C29 1.543(6) C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 C29 H29A 0.9800 C29 H29B 0.9800 C29 H29C 0.9800 C30 C31 1.529(8) C30 C32 1.543(6) C30 C33 1.542(7) C31 H31A 0.9800 C31 H31B 0.9800 C31 H31C 0.9800 C32 H32A 0.9800 C32 H32B 0.9800 C32 H32C 0.9800 C33 H33A 0.9800 C33 H33B 0.9800 C33 H33C 0.9800 C34 C35 1.534(8) C34 C36 1.504(8) C34 C37 1.552(7) C35 H35A 0.9800 C35 H35B 0.9800 C35 H35C 0.9800 C36 H36A 0.9800 C36 H36B 0.9800 C36 H36C 0.9800 C37 H37A 0.9800 C37 H37B 0.9800 C37 H37C 0.9800 C38 C39 1.653(9) C38 C40 1.467(9) C38 C41 1.527(7) C39 H39A 0.9800 C39 H39B 0.9800 C39 H39C 0.9800 C40 H40A 0.9800 C40 H40B 0.9800 C40 H40C 0.9800 C41 H41A 0.9800 C41 H41B 0.9800 C41 H41C 0.9800 B2 F3 1.4018 B2 F4 1.4033 B2 F5 1.4008 B2 F6 1.4026 B2A F3A 1.45(4) B2A F4A 1.36(3) B2A F5A 1.29(3) B2A F6A 1.42(3) Cl3 C44 1.716(8) Cl4 C44 1.735(8) C44 H44A 0.9900 C44 H44B 0.9900 Cl1 C42 1.734(6) Cl2 C42 1.738(6) C42 H42A 0.9900 C42 H42B 0.9900 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 Zn N1 C2 C1 -1.7(5) Zn N1 C2 C3 176.6(2) Zn N1 C5 C4 -176.5(2) Zn N1 C5 C6 3.2(5) Zn N2 C7 C6 -6.9(5) Zn N2 C7 C8 176.3(2) Zn N2 C10 C9 -176.5(2) Zn N2 C10 C11 4.2(5) Zn N3 C12 C11 -8.8(5) Zn N3 C12 C13 172.8(2) Zn N3 C15 C14 -172.7(2) Zn N3 C15 C16 7.5(5) Zn N4 C17 C16 -8.4(5) Zn N4 C17 C18 168.4(2) Zn N4 C20 C1 17.4(5) Zn N4 C20 C19 -165.0(2) C1 C2 C3 C4 177.6(3) C1 N5 C21 C22 172.4(3) C1 N5 C25 C24 -172.9(4) N1 C2 C3 C4 -0.7(4) N1 C5 C6 C7 3.6(6) C2 C1 N5 C21 -78.5(4) C2 C1 N5 C25 93.2(4) C2 C1 C20 N4 -3.9(6) C2 C1 C20 C19 179.2(4) C2 N1 C5 C4 -1.2(4) C2 N1 C5 C6 178.6(4) C2 C3 C4 C5 0.0(4) C2 C3 C4 C26 -178.1(4) N2 C7 C8 C9 0.9(4) N2 C10 C11 C12 1.5(6) C3 C4 C5 N1 0.7(4) C3 C4 C5 C6 -179.0(4) C3 C4 C26 C27 -122.0(5) C3 C4 C26 C28 114.7(5) C3 C4 C26 C29 -3.8(6) N3 C12 C13 C14 0.6(4) N3 C15 C16 C17 -2.6(6) C4 C5 C6 C7 -176.7(4) N4 C17 C18 C19 -1.5(5) C5 N1 C2 C1 -177.1(3) C5 N1 C2 C3 1.1(4) C5 C4 C26 C27 60.4(6) C5 C4 C26 C28 -62.9(6) C5 C4 C26 C29 178.6(4) C5 C6 C7 N2 -1.6(7) C5 C6 C7 C8 174.8(4) N5 C1 C2 N1 178.8(3) N5 C1 C2 C3 0.8(5) N5 C1 C20 N4 173.1(3) N5 C1 C20 C19 -3.9(6) N5 C21 C22 C23 0.4(6) C6 C7 C8 C9 -176.0(4) C7 N2 C10 C9 0.4(4) C7 N2 C10 C11 -178.8(3) C7 C8 C9 C10 -0.6(4) C7 C8 C9 C30 178.6(4) C8 C9 C10 N2 0.1(4) C8 C9 C10 C11 179.3(4) C8 C9 C30 C31 -117.4(5) C8 C9 C30 C32 120.0(5) C8 C9 C30 C33 2.5(7) C9 C10 C11 C12 -177.6(4) C10 N2 C7 C6 176.0(4) C10 N2 C7 C8 -0.8(4) C10 C9 C30 C31 61.6(5) C10 C9 C30 C32 -61.0(6) C10 C9 C30 C33 -178.5(4) C10 C11 C12 N3 1.0(6) C10 C11 C12 C13 179.1(4) C11 C12 C13 C14 -177.8(4) C12 N3 C15 C14 0.7(4) C12 N3 C15 C16 -179.0(3) C12 C13 C14 C15 -0.2(4) C12 C13 C14 C34 179.5(4) C13 C14 C15 N3 -0.3(4) C13 C14 C15 C16 179.4(4) C13 C14 C34 C35 120.1(5) C13 C14 C34 C36 -115.7(5) C13 C14 C34 C37 2.1(7) C14 C15 C16 C17 177.7(4) C15 N3 C12 C11 177.5(4) C15 N3 C12 C13 -0.8(4) C15 C14 C34 C35 -60.3(6) C15 C14 C34 C36 63.8(6) C15 C14 C34 C37 -178.4(5) C15 C16 C17 N4 3.5(7) C15 C16 C17 C18 -172.9(4) C16 C17 C18 C19 175.5(4) C17 N4 C20 C1 -173.8(3) C17 N4 C20 C19 3.8(4) C17 C18 C19 C20 3.6(4) C17 C18 C19 C38 -168.3(4) C18 C19 C20 C1 172.5(4) C18 C19 C20 N4 -4.6(4) C18 C19 C38 C39 110.8(5) C18 C19 C38 C40 -128.6(6) C18 C19 C38 C41 1.7(7) C20 C1 C2 N1 -4.0(6) C20 C1 C2 C3 178.0(4) C20 C1 N5 C21 104.0(4) C20 C1 N5 C25 -84.3(4) C20 N4 C17 C16 -178.3(4) C20 N4 C17 C18 -1.5(4) C20 C19 C38 C39 -58.2(6) C20 C19 C38 C40 62.4(8) C20 C19 C38 C41 -167.3(4) C21 N5 C25 C24 -1.4(6) C21 C22 C23 C24 -1.3(7) C22 C23 C24 C25 0.8(8) C23 C24 C25 N5 0.6(7) C25 N5 C21 C22 0.9(6) C26 C4 C5 N1 178.8(4) C26 C4 C5 C6 -1.0(7) C30 C9 C10 N2 -179.1(4) C30 C9 C10 C11 0.1(6) C34 C14 C15 N3 -180.0(4) C34 C14 C15 C16 -0.3(7) C38 C19 C20 C1 -17.2(8) C38 C19 C20 N4 165.7(5)