# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. # This journal is © The Royal Society of Chemistry 2019 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_6n _database_code_depnum_ccdc_archive 'CCDC 1893974' loop_ _audit_author_name _audit_author_address 'Attila Benyei' ;University of Debrecen Hungary ; _audit_update_record ; 2019-01-26 deposited with the CCDC. 2019-06-25 downloaded from the CCDC. ; _publcif_datablock.id {9966ffab-c497-4cb3-b4ab-ad01d3e31e95} _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C32 H28 Br4 Cu N4, F6 P' _chemical_formula_sum 'C32 H28 Br4 Cu F6 N4 P' _chemical_formula_iupac ? _chemical_formula_weight 996.73 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' 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' _cell_length_a 8.2994(7) _cell_length_b 23.795(2) _cell_length_c 18.3273(12) _cell_angle_alpha 90 _cell_angle_beta 93.367(3) _cell_angle_gamma 90 _cell_volume 3613.1(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1614 _cell_measurement_theta_min 1.7121 _cell_measurement_theta_max 21.7273 _cell_measurement_temperature 298.00(10) _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.585 _exptl_crystal_size_mid 0.162 _exptl_crystal_size_min 0.104 _exptl_crystal_density_diffrn 1.832 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 5.133 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_absorpt_correction_T_min 0.377 _exptl_absorpt_correction_T_max 0.745 _exptl_special_details ; ; _diffrn_ambient_temperature 298.00(10) _diffrn_source 'microfocus sealed tube' _diffrn_source_type 'INCOATEC I\mS 3.0' _diffrn_radiation_type ' Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'multilayer mirror' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\w and \p scan' _diffrn_detector_area_resol_mean 7.3910 _diffrn_reflns_number 53592 _diffrn_reflns_av_R_equivalents 0.1604 _diffrn_reflns_av_unetI/netI 0.0901 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.47 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _refine_special_details ; ; _reflns_number_total 6586 _reflns_number_gt 4230 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1364 _refine_ls_R_factor_gt 0.0872 _refine_ls_wR_factor_gt 0.1667 _refine_ls_wR_factor_ref 0.1897 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _refine_ls_number_reflns 6586 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+5.8845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.269 _refine_diff_density_min -0.666 _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_extinction_coef 0.0023(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' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service vV6.2.6' _computing_cell_refinement 'APEX3 v2017.3-0 (Bruker AXS)' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_molecular_graphics Mercury _computing_publication_material PublCIF loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C2 0.2785(10) 0.2903(3) 0.5482(4) 0.0409(18) Uani d . . . 1 . . H H2A 0.354171 0.292234 0.590489 0.049 Uiso calc U . R 1 . . H H2B 0.181219 0.271799 0.562688 0.049 Uiso calc U . R 1 . . C C3 0.2387(10) 0.3486(3) 0.5211(4) 0.0419(19) Uani d . . . 1 . . H H3A 0.177268 0.368257 0.556618 0.05 Uiso calc U . R 1 . . H H3B 0.337488 0.369377 0.51496 0.05 Uiso calc U . R 1 . . C C6 0.1417(14) 0.2288(4) 0.2558(4) 0.074(3) Uani d . . . 1 . . H H6A 0.050129 0.251891 0.239688 0.088 Uiso calc U . R 1 . . H H6B 0.137003 0.19422 0.227707 0.088 Uiso calc U . R 1 . . C C7 0.2932(14) 0.2589(4) 0.2434(4) 0.070(3) Uani d . . . 1 . . H H7A 0.383209 0.232892 0.248469 0.084 Uiso calc U . R 1 . . H H7B 0.288626 0.273782 0.194035 0.084 Uiso calc U . R 1 . . C C10 0.4474(10) 0.2189(3) 0.5093(4) 0.0436(19) Uani d . . . 1 . . H H10 0.469796 0.212153 0.558848 0.052 Uiso calc U . R 1 . . C C11 0.5260(9) 0.1843(3) 0.4559(4) 0.0419(19) Uani d . . . 1 . . C C12 0.5574(10) 0.1275(3) 0.4677(4) 0.048(2) Uani d . . . 1 . . C C13 0.6308(12) 0.0949(4) 0.4164(6) 0.065(3) Uani d . . . 1 . . H H13 0.649784 0.056913 0.424881 0.078 Uiso calc U . R 1 . . C C14 0.6746(12) 0.1195(4) 0.3535(5) 0.068(3) Uani d . . . 1 . . H H14 0.723871 0.097892 0.318863 0.082 Uiso calc U . R 1 . . C C15 0.6473(12) 0.1758(4) 0.3403(5) 0.065(3) Uani d . . . 1 . . H H15 0.679506 0.192331 0.297617 0.079 Uiso calc U . R 1 . . C C16 0.5726(11) 0.2067(4) 0.3907(5) 0.056(2) Uani d . . . 1 . . H H16 0.551907 0.244473 0.381023 0.067 Uiso calc U . R 1 . . C C40 0.0466(10) 0.3847(3) 0.4350(4) 0.048(2) Uani d . . . 1 . . H H40 0.037278 0.414007 0.468065 0.057 Uiso calc U . R 1 . . C C41 -0.0512(9) 0.3863(3) 0.3671(4) 0.0437(19) Uani d . . . 1 . . C C42 -0.0966(11) 0.4371(4) 0.3333(5) 0.058(2) Uani d . . . 1 . . C C43 -0.1895(13) 0.4384(6) 0.2688(6) 0.079(3) Uani d . . . 1 . . H H43 -0.215694 0.47265 0.246621 0.095 Uiso calc U . R 1 . . C C44 -0.2429(12) 0.3898(6) 0.2376(6) 0.075(3) Uani d . . . 1 . . H H44 -0.306902 0.390638 0.194194 0.091 Uiso calc U . R 1 . . C C45 -0.2021(12) 0.3387(5) 0.2702(6) 0.077(3) Uani d . . . 1 . . H H45 -0.238075 0.30521 0.248861 0.093 Uiso calc U . R 1 . . C C46 -0.1100(11) 0.3383(4) 0.3331(5) 0.062(2) Uani d . . . 1 . . H H46 -0.084826 0.303751 0.354678 0.074 Uiso calc U . R 1 . . C C50 0.0846(11) 0.1673(4) 0.3517(4) 0.056(2) Uani d . . . 1 . . H H50 0.063363 0.141417 0.31435 0.067 Uiso calc U . R 1 . . C C51 0.0590(10) 0.1498(3) 0.4254(4) 0.048(2) Uani d . . . 1 . . C C52 0.0877(11) 0.0960(3) 0.4504(5) 0.053(2) Uani d . . . 1 . . C C53 0.0559(12) 0.0789(4) 0.5198(5) 0.061(2) Uani d . . . 1 . . H H53 0.078687 0.042231 0.534722 0.074 Uiso calc U . R 1 . . C C54 -0.0094(11) 0.1161(4) 0.5667(5) 0.064(3) Uani d . . . 1 . . H H54 -0.033135 0.10486 0.613448 0.076 Uiso calc U . R 1 . . C C55 -0.0395(11) 0.1702(4) 0.5437(5) 0.061(2) Uani d . . . 1 . . H H55 -0.084102 0.19568 0.57533 0.073 Uiso calc U . R 1 . . C C56 -0.0048(11) 0.1873(4) 0.4751(5) 0.056(2) Uani d . . . 1 . . H H56 -0.023886 0.224365 0.461166 0.067 Uiso calc U . R 1 . . C C80 0.3566(11) 0.3527(3) 0.2709(4) 0.052(2) Uani d . . . 1 . . H H80 0.354767 0.356709 0.220344 0.062 Uiso calc U . R 1 . . C C81 0.4031(10) 0.4012(3) 0.3156(4) 0.045(2) Uani d . . . 1 . . C C82 0.3702(11) 0.4560(3) 0.2925(4) 0.048(2) Uani d . . . 1 . . C C83 0.4231(13) 0.5015(4) 0.3325(5) 0.065(3) Uani d . . . 1 . . H H83 0.398339 0.537663 0.316151 0.078 Uiso calc U . R 1 . . C C84 0.5119(12) 0.4936(4) 0.3961(5) 0.065(3) Uani d . . . 1 . . H H84 0.549359 0.524493 0.423155 0.078 Uiso calc U . R 1 . . C C85 0.5468(11) 0.4405(4) 0.4208(5) 0.059(2) Uani d . . . 1 . . H H85 0.608513 0.435527 0.464351 0.071 Uiso calc U . R 1 . . C C86 0.4915(10) 0.3946(3) 0.3818(4) 0.047(2) Uani d . . . 1 . . H H86 0.513327 0.358639 0.399756 0.057 Uiso calc U . R 1 . . N N1 0.3493(7) 0.2580(3) 0.4900(3) 0.0346(14) Uani d . . . 1 . . N N4 0.1446(8) 0.3451(3) 0.4514(3) 0.0390(15) Uani d . . . 1 . . N N5 0.1343(9) 0.2159(3) 0.3340(3) 0.0487(17) Uani d . . . 1 . . N N8 0.3184(9) 0.3052(3) 0.2962(3) 0.0488(17) Uani d . . . 1 . . F F1 0.8208(10) 0.3882(3) 0.5750(4) 0.110(2) Uani d . . . 1 . . F F2 0.8157(9) 0.3577(3) 0.6880(3) 0.112(2) Uani d . . . 1 . . F F3 0.9246(8) 0.3059(4) 0.6033(5) 0.131(3) Uani d . . . 1 . . F F4 0.6908(10) 0.2788(3) 0.6464(4) 0.115(2) Uani d . . . 1 . . F F5 0.5929(8) 0.3622(3) 0.6209(6) 0.146(4) Uani d . . . 1 . . F F6 0.6978(11) 0.3107(4) 0.5357(4) 0.134(3) Uani d . . . 1 . . P P1 0.7576(3) 0.33353(10) 0.61172(12) 0.0511(6) Uani d . . . 1 . . Cu Cu1 0.23599(12) 0.28059(4) 0.39330(4) 0.0410(3) Uani d . . . 1 . . Br Br12 0.49469(13) 0.09209(4) 0.55419(5) 0.0673(3) Uani d . . . 1 . . Br Br42 -0.02045(15) 0.50611(4) 0.37390(7) 0.0851(4) Uani d . . . 1 . . Br Br52 0.17745(18) 0.04191(4) 0.38813(7) 0.0906(4) Uani d . . . 1 . . Br Br82 0.24754(16) 0.46818(5) 0.20364(6) 0.0821(4) Uani d . . . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C2 0.043(5) 0.045(4) 0.035(4) 0.004(4) 0.009(3) 0.001(3) C3 0.041(5) 0.047(5) 0.037(4) 0.004(4) 0.004(4) -0.009(3) C6 0.120(9) 0.069(6) 0.031(4) -0.022(6) 0.002(5) -0.007(4) C7 0.119(9) 0.055(6) 0.038(4) -0.014(6) 0.023(5) -0.010(4) C10 0.043(5) 0.043(5) 0.045(4) 0.002(4) 0.001(4) 0.007(4) C11 0.033(5) 0.044(5) 0.048(4) 0.012(4) -0.004(4) -0.001(4) C12 0.036(5) 0.052(5) 0.054(5) -0.001(4) -0.003(4) 0.002(4) C13 0.062(7) 0.046(5) 0.087(7) 0.003(5) 0.007(6) -0.015(5) C14 0.074(7) 0.064(6) 0.068(6) 0.014(5) 0.020(5) -0.021(5) C15 0.072(7) 0.063(6) 0.064(6) 0.019(5) 0.022(5) -0.001(5) C16 0.065(6) 0.046(5) 0.058(5) 0.019(4) 0.021(5) 0.007(4) C40 0.053(6) 0.042(5) 0.049(5) 0.008(4) 0.008(4) -0.005(4) C41 0.037(5) 0.052(5) 0.042(4) 0.012(4) 0.007(4) 0.000(4) C42 0.045(6) 0.068(6) 0.061(5) 0.009(5) 0.012(5) 0.012(5) C43 0.059(7) 0.114(10) 0.066(6) 0.006(7) 0.010(6) 0.049(7) C44 0.047(7) 0.122(10) 0.057(6) 0.005(7) -0.001(5) 0.003(7) C45 0.055(7) 0.110(9) 0.066(6) 0.018(6) -0.004(5) -0.023(6) C46 0.058(6) 0.060(6) 0.067(6) 0.011(5) -0.002(5) -0.007(5) C50 0.068(7) 0.051(5) 0.048(5) -0.017(5) 0.002(4) -0.008(4) C51 0.041(5) 0.049(5) 0.054(5) -0.018(4) 0.003(4) -0.001(4) C52 0.058(6) 0.045(5) 0.055(5) -0.014(4) 0.001(4) -0.005(4) C53 0.066(7) 0.045(5) 0.073(6) -0.007(5) 0.000(5) 0.016(5) C54 0.062(7) 0.071(7) 0.060(6) -0.010(5) 0.014(5) 0.011(5) C55 0.057(6) 0.064(6) 0.064(6) -0.008(5) 0.018(5) -0.009(5) C56 0.062(6) 0.040(5) 0.066(6) -0.003(4) 0.007(5) -0.003(4) C80 0.070(6) 0.054(5) 0.032(4) -0.001(5) 0.015(4) -0.003(4) C81 0.058(6) 0.040(4) 0.039(4) -0.004(4) 0.021(4) -0.002(3) C82 0.060(6) 0.040(5) 0.044(4) -0.001(4) 0.013(4) 0.005(4) C83 0.097(8) 0.043(5) 0.057(6) 0.002(5) 0.016(5) -0.004(4) C84 0.069(7) 0.058(6) 0.068(6) -0.012(5) 0.018(5) -0.025(5) C85 0.060(6) 0.070(6) 0.047(5) -0.001(5) 0.008(4) -0.011(5) C86 0.056(6) 0.043(5) 0.044(4) 0.002(4) 0.017(4) 0.005(4) N1 0.028(4) 0.041(3) 0.035(3) 0.001(3) 0.002(3) -0.002(3) N4 0.042(4) 0.042(4) 0.034(3) 0.005(3) 0.008(3) 0.000(3) N5 0.061(5) 0.049(4) 0.037(3) -0.014(4) 0.005(3) 0.000(3) N8 0.077(5) 0.040(4) 0.031(3) -0.006(4) 0.017(3) -0.006(3) F1 0.150(7) 0.081(4) 0.100(5) -0.050(4) 0.007(4) 0.005(4) F2 0.128(6) 0.147(6) 0.062(4) -0.033(5) 0.005(4) -0.021(4) F3 0.070(5) 0.148(7) 0.178(8) 0.033(5) 0.026(5) -0.025(6) F4 0.149(7) 0.075(4) 0.123(6) -0.025(4) 0.031(5) 0.025(4) F5 0.065(5) 0.102(5) 0.270(11) 0.022(4) -0.003(5) -0.036(6) F6 0.174(8) 0.143(7) 0.081(5) -0.060(6) -0.021(5) -0.025(4) P1 0.0443(14) 0.0524(14) 0.0565(13) 0.0017(11) 0.0019(11) -0.0040(10) Cu1 0.0532(7) 0.0400(5) 0.0302(5) 0.0018(5) 0.0055(4) -0.0032(4) Br12 0.0802(8) 0.0574(6) 0.0636(6) -0.0027(5) -0.0029(5) 0.0120(4) Br42 0.0883(9) 0.0544(6) 0.1132(9) 0.0038(6) 0.0117(7) 0.0165(6) Br52 0.1278(11) 0.0540(6) 0.0923(8) 0.0006(6) 0.0249(7) -0.0201(6) Br82 0.1173(10) 0.0675(7) 0.0599(6) -0.0015(6) -0.0081(6) 0.0157(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C2 N1 . 1.464(9) ? C2 C3 . 1.503(10) ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 N4 . 1.460(9) ? C3 H3A . 0.97 ? C3 H3B . 0.97 ? C6 N5 . 1.471(10) ? C6 C7 . 1.476(14) ? C6 H6A . 0.97 ? C6 H6B . 0.97 ? C7 N8 . 1.475(10) ? C7 H7A . 0.97 ? C7 H7B . 0.97 ? C10 N1 . 1.273(9) ? C10 C11 . 1.461(11) ? C10 H10 . 0.93 ? C11 C16 . 1.384(11) ? C11 C12 . 1.392(11) ? C12 C13 . 1.385(12) ? C12 Br12 . 1.895(8) ? C13 C14 . 1.361(13) ? C13 H13 . 0.93 ? C14 C15 . 1.377(13) ? C14 H14 . 0.93 ? C15 C16 . 1.359(11) ? C15 H15 . 0.93 ? C16 H16 . 0.93 ? C40 N4 . 1.270(10) ? C40 C41 . 1.446(11) ? C40 H40 . 0.93 ? C41 C46 . 1.377(12) ? C41 C42 . 1.400(12) ? C42 C43 . 1.374(13) ? C42 Br42 . 1.895(10) ? C43 C44 . 1.354(15) ? C43 H43 . 0.93 ? C44 C45 . 1.388(15) ? C44 H44 . 0.93 ? C45 C46 . 1.344(13) ? C45 H45 . 0.93 ? C46 H46 . 0.93 ? C50 N5 . 1.275(10) ? C50 C51 . 1.443(11) ? C50 H50 . 0.93 ? C51 C52 . 1.376(11) ? C51 C56 . 1.399(12) ? C52 C53 . 1.375(12) ? C52 Br52 . 1.901(9) ? C53 C54 . 1.368(13) ? C53 H53 . 0.93 ? C54 C55 . 1.373(13) ? C54 H54 . 0.93 ? C55 C56 . 1.369(12) ? C55 H55 . 0.93 ? C56 H56 . 0.93 ? C80 N8 . 1.268(10) ? C80 C81 . 1.454(11) ? C80 H80 . 0.93 ? C81 C86 . 1.389(11) ? C81 C82 . 1.394(10) ? C82 C83 . 1.365(12) ? C82 Br82 . 1.891(8) ? C83 C84 . 1.356(13) ? C83 H83 . 0.93 ? C84 C85 . 1.367(13) ? C84 H84 . 0.93 ? C85 C86 . 1.371(12) ? C85 H85 . 0.93 ? C86 H86 . 0.93 ? N1 Cu1 . 2.030(6) ? N4 Cu1 . 2.040(6) ? N5 Cu1 . 2.038(6) ? N8 Cu1 . 2.030(6) ? F1 P1 . 1.568(6) ? F2 P1 . 1.561(6) ? F3 P1 . 1.550(7) ? F4 P1 . 1.565(6) ? F5 P1 . 1.545(7) ? F6 P1 . 1.550(7) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 C2 C3 . . 109.5(6) ? N1 C2 H2A . . 109.8 ? C3 C2 H2A . . 109.8 ? N1 C2 H2B . . 109.8 ? C3 C2 H2B . . 109.8 ? H2A C2 H2B . . 108.2 ? N4 C3 C2 . . 109.4(6) ? N4 C3 H3A . . 109.8 ? C2 C3 H3A . . 109.8 ? N4 C3 H3B . . 109.8 ? C2 C3 H3B . . 109.8 ? H3A C3 H3B . . 108.2 ? N5 C6 C7 . . 109.7(8) ? N5 C6 H6A . . 109.7 ? C7 C6 H6A . . 109.7 ? N5 C6 H6B . . 109.7 ? C7 C6 H6B . . 109.7 ? H6A C6 H6B . . 108.2 ? N8 C7 C6 . . 110.6(7) ? N8 C7 H7A . . 109.5 ? C6 C7 H7A . . 109.5 ? N8 C7 H7B . . 109.5 ? C6 C7 H7B . . 109.5 ? H7A C7 H7B . . 108.1 ? N1 C10 C11 . . 122.0(7) ? N1 C10 H10 . . 119.0 ? C11 C10 H10 . . 119.0 ? C16 C11 C12 . . 116.7(7) ? C16 C11 C10 . . 121.3(7) ? C12 C11 C10 . . 122.1(7) ? C13 C12 C11 . . 121.6(8) ? C13 C12 Br12 . . 118.2(7) ? C11 C12 Br12 . . 120.2(6) ? C14 C13 C12 . . 119.0(9) ? C14 C13 H13 . . 120.5 ? C12 C13 H13 . . 120.5 ? C13 C14 C15 . . 121.1(8) ? C13 C14 H14 . . 119.5 ? C15 C14 H14 . . 119.5 ? C16 C15 C14 . . 119.0(9) ? C16 C15 H15 . . 120.5 ? C14 C15 H15 . . 120.5 ? C15 C16 C11 . . 122.7(8) ? C15 C16 H16 . . 118.7 ? C11 C16 H16 . . 118.7 ? N4 C40 C41 . . 122.9(7) ? N4 C40 H40 . . 118.6 ? C41 C40 H40 . . 118.6 ? C46 C41 C42 . . 116.0(8) ? C46 C41 C40 . . 122.3(8) ? C42 C41 C40 . . 121.7(8) ? C43 C42 C41 . . 121.5(10) ? C43 C42 Br42 . . 118.4(8) ? C41 C42 Br42 . . 120.0(7) ? C44 C43 C42 . . 119.8(10) ? C44 C43 H43 . . 120.1 ? C42 C43 H43 . . 120.1 ? C43 C44 C45 . . 120.0(10) ? C43 C44 H44 . . 120.0 ? C45 C44 H44 . . 120.0 ? C46 C45 C44 . . 119.3(11) ? C46 C45 H45 . . 120.4 ? C44 C45 H45 . . 120.4 ? C45 C46 C41 . . 123.3(10) ? C45 C46 H46 . . 118.3 ? C41 C46 H46 . . 118.3 ? N5 C50 C51 . . 124.6(8) ? N5 C50 H50 . . 117.7 ? C51 C50 H50 . . 117.7 ? C52 C51 C56 . . 116.2(8) ? C52 C51 C50 . . 123.3(8) ? C56 C51 C50 . . 120.5(8) ? C53 C52 C51 . . 123.0(8) ? C53 C52 Br52 . . 117.3(7) ? C51 C52 Br52 . . 119.7(7) ? C54 C53 C52 . . 119.6(8) ? C54 C53 H53 . . 120.2 ? C52 C53 H53 . . 120.2 ? C53 C54 C55 . . 119.1(9) ? C53 C54 H54 . . 120.4 ? C55 C54 H54 . . 120.4 ? C56 C55 C54 . . 121.0(9) ? C56 C55 H55 . . 119.5 ? C54 C55 H55 . . 119.5 ? C55 C56 C51 . . 121.1(8) ? C55 C56 H56 . . 119.4 ? C51 C56 H56 . . 119.4 ? N8 C80 C81 . . 124.3(7) ? N8 C80 H80 . . 117.8 ? C81 C80 H80 . . 117.8 ? C86 C81 C82 . . 117.1(7) ? C86 C81 C80 . . 120.8(7) ? C82 C81 C80 . . 122.1(8) ? C83 C82 C81 . . 121.9(8) ? C83 C82 Br82 . . 118.7(6) ? C81 C82 Br82 . . 119.4(6) ? C84 C83 C82 . . 119.6(9) ? C84 C83 H83 . . 120.2 ? C82 C83 H83 . . 120.2 ? C83 C84 C85 . . 120.5(9) ? C83 C84 H84 . . 119.8 ? C85 C84 H84 . . 119.8 ? C84 C85 C86 . . 120.4(9) ? C84 C85 H85 . . 119.8 ? C86 C85 H85 . . 119.8 ? C85 C86 C81 . . 120.6(8) ? C85 C86 H86 . . 119.7 ? C81 C86 H86 . . 119.7 ? C10 N1 C2 . . 117.3(6) ? C10 N1 Cu1 . . 133.8(5) ? C2 N1 Cu1 . . 108.1(4) ? C40 N4 C3 . . 117.9(6) ? C40 N4 Cu1 . . 133.4(5) ? C3 N4 Cu1 . . 107.7(5) ? C50 N5 C6 . . 117.9(7) ? C50 N5 Cu1 . . 132.8(6) ? C6 N5 Cu1 . . 108.8(5) ? C80 N8 C7 . . 117.0(6) ? C80 N8 Cu1 . . 133.0(5) ? C7 N8 Cu1 . . 108.5(5) ? F5 P1 F3 . . 178.8(5) ? F5 P1 F6 . . 90.8(5) ? F3 P1 F6 . . 90.2(5) ? F5 P1 F2 . . 88.2(5) ? F3 P1 F2 . . 90.8(5) ? F6 P1 F2 . . 178.8(5) ? F5 P1 F4 . . 89.2(5) ? F3 P1 F4 . . 91.6(5) ? F6 P1 F4 . . 88.4(4) ? F2 P1 F4 . . 92.3(4) ? F5 P1 F1 . . 90.1(5) ? F3 P1 F1 . . 89.1(5) ? F6 P1 F1 . . 90.2(4) ? F2 P1 F1 . . 89.2(4) ? F4 P1 F1 . . 178.3(4) ? N1 Cu1 N8 . . 132.8(3) ? N1 Cu1 N5 . . 114.9(2) ? N8 Cu1 N5 . . 84.3(3) ? N1 Cu1 N4 . . 84.9(2) ? N8 Cu1 N4 . . 113.3(2) ? N5 Cu1 N4 . . 133.8(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C2 C3 N4 . . . . 50.9(8) ? N5 C6 C7 N8 . . . . -48.0(11) ? N1 C10 C11 C16 . . . . 35.6(12) ? N1 C10 C11 C12 . . . . -144.2(8) ? C16 C11 C12 C13 . . . . -0.4(12) ? C10 C11 C12 C13 . . . . 179.5(8) ? C16 C11 C12 Br12 . . . . -178.7(6) ? C10 C11 C12 Br12 . . . . 1.1(11) ? C11 C12 C13 C14 . . . . 0.7(14) ? Br12 C12 C13 C14 . . . . 179.1(7) ? C12 C13 C14 C15 . . . . 0.1(15) ? C13 C14 C15 C16 . . . . -1.2(16) ? C14 C15 C16 C11 . . . . 1.6(15) ? C12 C11 C16 C15 . . . . -0.9(14) ? C10 C11 C16 C15 . . . . 179.3(9) ? N4 C40 C41 C46 . . . . 33.3(13) ? N4 C40 C41 C42 . . . . -149.1(8) ? C46 C41 C42 C43 . . . . -2.3(13) ? C40 C41 C42 C43 . . . . 180.0(8) ? C46 C41 C42 Br42 . . . . -178.9(6) ? C40 C41 C42 Br42 . . . . 3.3(11) ? C41 C42 C43 C44 . . . . 1.9(15) ? Br42 C42 C43 C44 . . . . 178.6(8) ? C42 C43 C44 C45 . . . . -0.8(16) ? C43 C44 C45 C46 . . . . 0.3(16) ? C44 C45 C46 C41 . . . . -0.8(16) ? C42 C41 C46 C45 . . . . 1.8(14) ? C40 C41 C46 C45 . . . . 179.5(9) ? N5 C50 C51 C52 . . . . -145.0(10) ? N5 C50 C51 C56 . . . . 37.9(14) ? C56 C51 C52 C53 . . . . 0.3(13) ? C50 C51 C52 C53 . . . . -176.8(8) ? C56 C51 C52 Br52 . . . . -179.0(6) ? C50 C51 C52 Br52 . . . . 3.8(12) ? C51 C52 C53 C54 . . . . 1.0(15) ? Br52 C52 C53 C54 . . . . -179.7(7) ? C52 C53 C54 C55 . . . . -1.1(14) ? C53 C54 C55 C56 . . . . -0.1(15) ? C54 C55 C56 C51 . . . . 1.5(14) ? C52 C51 C56 C55 . . . . -1.5(13) ? C50 C51 C56 C55 . . . . 175.7(8) ? N8 C80 C81 C86 . . . . 35.4(13) ? N8 C80 C81 C82 . . . . -148.5(9) ? C86 C81 C82 C83 . . . . 0.5(12) ? C80 C81 C82 C83 . . . . -175.7(8) ? C86 C81 C82 Br82 . . . . -179.0(6) ? C80 C81 C82 Br82 . . . . 4.8(11) ? C81 C82 C83 C84 . . . . 0.8(14) ? Br82 C82 C83 C84 . . . . -179.6(7) ? C82 C83 C84 C85 . . . . -0.9(15) ? C83 C84 C85 C86 . . . . -0.5(14) ? C84 C85 C86 C81 . . . . 1.8(13) ? C82 C81 C86 C85 . . . . -1.8(12) ? C80 C81 C86 C85 . . . . 174.4(8) ? C11 C10 N1 C2 . . . . -179.6(7) ? C11 C10 N1 Cu1 . . . . 11.6(12) ? C3 C2 N1 C10 . . . . 151.7(7) ? C3 C2 N1 Cu1 . . . . -36.8(7) ? C41 C40 N4 C3 . . . . 179.1(7) ? C41 C40 N4 Cu1 . . . . 12.2(13) ? C2 C3 N4 C40 . . . . 151.6(7) ? C2 C3 N4 Cu1 . . . . -38.4(7) ? C51 C50 N5 C6 . . . . -175.1(9) ? C51 C50 N5 Cu1 . . . . 13.5(15) ? C7 C6 N5 C50 . . . . -137.4(9) ? C7 C6 N5 Cu1 . . . . 35.9(9) ? C81 C80 N8 C7 . . . . -173.0(9) ? C81 C80 N8 Cu1 . . . . 22.5(14) ? C6 C7 N8 C80 . . . . -132.4(9) ? C6 C7 N8 Cu1 . . . . 35.8(9) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2A F5 . 0.97 2.62 3.332(11) 130.2 ? C2 H2B F3 1_455 0.97 2.44 3.183(10) 133.6 ? C43 H43 Br52 2 0.93 3.00 3.792(9) 143.8 ? _shelx_res_file ; TITL mo_18120_1_0m_a.res in P2(1)/c mo_18120_1_0m.res created by SHELXL-2016/6 at 10:34:10 on 20-Nov-2018 CELL 0.71073 8.2994 23.7955 18.3273 90.000 93.367 90.000 ZERR 4.00 0.0007 0.0020 0.0012 0.000 0.003 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N F P CU Br UNIT 128 112 16 24 4 4 16 LIST 4 TEMP 25 ACTA 50 L.S. 14 FMAP 2 PLAN 5 HTAB HTAB C2 F5 EQIV $1 x-1, y, z HTAB C2 F3_$1 EQIV $2 -x, y+1/2, -z+1/2 HTAB C43 Br52_$2 BOND $H CONF WGHT 0.070500 5.884501 EXTI 0.002316 FVAR 0.21202 C2 1 0.278492 0.290269 0.548175 11.00000 0.04340 0.04457 = 0.03547 0.00077 0.00863 0.00408 AFIX 23 H2A 2 0.354171 0.292234 0.590489 11.00000 -1.20000 H2B 2 0.181219 0.271799 0.562688 11.00000 -1.20000 AFIX 0 C3 1 0.238711 0.348574 0.521149 11.00000 0.04108 0.04729 = 0.03742 -0.00880 0.00371 0.00411 AFIX 23 H3A 2 0.177268 0.368257 0.556618 11.00000 -1.20000 H3B 2 0.337488 0.369377 0.514960 11.00000 -1.20000 AFIX 0 C6 1 0.141735 0.228792 0.255793 11.00000 0.12029 0.06887 = 0.03131 -0.00711 0.00163 -0.02172 AFIX 23 H6A 2 0.050129 0.251891 0.239688 11.00000 -1.20000 H6B 2 0.137003 0.194220 0.227707 11.00000 -1.20000 AFIX 0 C7 1 0.293175 0.258866 0.243369 11.00000 0.11883 0.05518 = 0.03796 -0.01023 0.02297 -0.01395 AFIX 23 H7A 2 0.383209 0.232892 0.248469 11.00000 -1.20000 H7B 2 0.288626 0.273782 0.194035 11.00000 -1.20000 AFIX 0 C10 1 0.447446 0.218910 0.509306 11.00000 0.04260 0.04328 = 0.04463 0.00659 0.00056 0.00214 AFIX 43 H10 2 0.469796 0.212153 0.558848 11.00000 -1.20000 AFIX 0 C11 1 0.526021 0.184314 0.455911 11.00000 0.03314 0.04360 = 0.04824 -0.00109 -0.00371 0.01176 C12 1 0.557416 0.127458 0.467661 11.00000 0.03618 0.05180 = 0.05420 0.00197 -0.00267 -0.00053 C13 1 0.630782 0.094942 0.416424 11.00000 0.06245 0.04560 = 0.08672 -0.01512 0.00680 0.00292 AFIX 43 H13 2 0.649784 0.056913 0.424881 11.00000 -1.20000 AFIX 0 C14 1 0.674636 0.119480 0.353525 11.00000 0.07389 0.06416 = 0.06781 -0.02127 0.02007 0.01368 AFIX 43 H14 2 0.723871 0.097892 0.318863 11.00000 -1.20000 AFIX 0 C15 1 0.647311 0.175757 0.340350 11.00000 0.07229 0.06254 = 0.06355 -0.00083 0.02173 0.01852 AFIX 43 H15 2 0.679506 0.192331 0.297617 11.00000 -1.20000 AFIX 0 C16 1 0.572577 0.206713 0.390742 11.00000 0.06483 0.04581 = 0.05810 0.00731 0.02070 0.01875 AFIX 43 H16 2 0.551907 0.244473 0.381023 11.00000 -1.20000 AFIX 0 C40 1 0.046589 0.384719 0.434978 11.00000 0.05276 0.04209 = 0.04915 -0.00542 0.00761 0.00825 AFIX 43 H40 2 0.037278 0.414007 0.468065 11.00000 -1.20000 AFIX 0 C41 1 -0.051171 0.386274 0.367060 11.00000 0.03703 0.05225 = 0.04243 0.00029 0.00651 0.01232 C42 1 -0.096601 0.437120 0.333333 11.00000 0.04516 0.06800 = 0.06052 0.01239 0.01202 0.00877 C43 1 -0.189514 0.438435 0.268799 11.00000 0.05896 0.11367 = 0.06551 0.04948 0.00967 0.00630 AFIX 43 H43 2 -0.215694 0.472650 0.246621 11.00000 -1.20000 AFIX 0 C44 1 -0.242878 0.389812 0.237563 11.00000 0.04703 0.12218 = 0.05668 0.00330 -0.00075 0.00496 AFIX 43 H44 2 -0.306902 0.390638 0.194194 11.00000 -1.20000 AFIX 0 C45 1 -0.202105 0.338733 0.270219 11.00000 0.05458 0.10971 = 0.06613 -0.02268 -0.00448 0.01778 AFIX 43 H45 2 -0.238075 0.305210 0.248861 11.00000 -1.20000 AFIX 0 C46 1 -0.110038 0.338252 0.333066 11.00000 0.05783 0.06022 = 0.06740 -0.00659 -0.00231 0.01051 AFIX 43 H46 2 -0.084826 0.303751 0.354678 11.00000 -1.20000 AFIX 0 C50 1 0.084607 0.167343 0.351653 11.00000 0.06822 0.05102 = 0.04771 -0.00842 0.00246 -0.01700 AFIX 43 H50 2 0.063363 0.141417 0.314350 11.00000 -1.20000 AFIX 0 C51 1 0.059028 0.149807 0.425443 11.00000 0.04090 0.04928 = 0.05388 -0.00117 0.00263 -0.01836 C52 1 0.087718 0.095980 0.450450 11.00000 0.05766 0.04504 = 0.05487 -0.00511 0.00091 -0.01377 C53 1 0.055921 0.078875 0.519784 11.00000 0.06603 0.04482 = 0.07268 0.01614 0.00050 -0.00668 AFIX 43 H53 2 0.078687 0.042231 0.534722 11.00000 -1.20000 AFIX 0 C54 1 -0.009400 0.116074 0.566668 11.00000 0.06185 0.07092 = 0.05968 0.01073 0.01378 -0.00958 AFIX 43 H54 2 -0.033135 0.104860 0.613448 11.00000 -1.20000 AFIX 0 C55 1 -0.039475 0.170216 0.543732 11.00000 0.05672 0.06363 = 0.06428 -0.00865 0.01816 -0.00788 AFIX 43 H55 2 -0.084102 0.195680 0.575330 11.00000 -1.20000 AFIX 0 C56 1 -0.004759 0.187261 0.475072 11.00000 0.06220 0.03977 = 0.06559 -0.00348 0.00683 -0.00256 AFIX 43 H56 2 -0.023886 0.224365 0.461166 11.00000 -1.20000 AFIX 0 C80 1 0.356615 0.352659 0.270857 11.00000 0.07024 0.05436 = 0.03158 -0.00283 0.01469 -0.00125 AFIX 43 H80 2 0.354767 0.356709 0.220344 11.00000 -1.20000 AFIX 0 C81 1 0.403111 0.401154 0.315577 11.00000 0.05751 0.03955 = 0.03944 -0.00203 0.02105 -0.00388 C82 1 0.370195 0.456013 0.292479 11.00000 0.06004 0.04025 = 0.04374 0.00523 0.01272 -0.00086 C83 1 0.423072 0.501495 0.332455 11.00000 0.09691 0.04275 = 0.05747 -0.00393 0.01570 0.00160 AFIX 43 H83 2 0.398339 0.537663 0.316151 11.00000 -1.20000 AFIX 0 C84 1 0.511922 0.493588 0.396112 11.00000 0.06919 0.05830 = 0.06809 -0.02512 0.01808 -0.01224 AFIX 43 H84 2 0.549359 0.524493 0.423155 11.00000 -1.20000 AFIX 0 C85 1 0.546843 0.440502 0.420806 11.00000 0.06038 0.06956 = 0.04707 -0.01077 0.00819 -0.00119 AFIX 43 H85 2 0.608513 0.435527 0.464351 11.00000 -1.20000 AFIX 0 C86 1 0.491496 0.394553 0.381763 11.00000 0.05642 0.04266 = 0.04404 0.00525 0.01673 0.00155 AFIX 43 H86 2 0.513327 0.358639 0.399756 11.00000 -1.20000 AFIX 0 N1 3 0.349343 0.258009 0.490024 11.00000 0.02786 0.04128 = 0.03458 -0.00163 0.00178 0.00070 N4 3 0.144633 0.345092 0.451422 11.00000 0.04185 0.04163 = 0.03409 -0.00019 0.00821 0.00483 N5 3 0.134306 0.215905 0.334032 11.00000 0.06054 0.04922 = 0.03666 -0.00005 0.00544 -0.01394 N8 3 0.318441 0.305234 0.296196 11.00000 0.07654 0.04027 = 0.03116 -0.00592 0.01723 -0.00621 F1 4 0.820816 0.388170 0.575030 11.00000 0.15047 0.08092 = 0.09969 0.00496 0.00673 -0.05026 F2 4 0.815682 0.357661 0.687994 11.00000 0.12810 0.14667 = 0.06222 -0.02109 0.00451 -0.03265 F3 4 0.924634 0.305936 0.603297 11.00000 0.07022 0.14768 = 0.17784 -0.02465 0.02604 0.03329 F4 4 0.690818 0.278818 0.646433 11.00000 0.14899 0.07537 = 0.12253 0.02464 0.03105 -0.02534 F5 4 0.592922 0.362160 0.620859 11.00000 0.06458 0.10182 = 0.27041 -0.03617 -0.00321 0.02175 F6 4 0.697774 0.310681 0.535677 11.00000 0.17449 0.14297 = 0.08085 -0.02488 -0.02146 -0.06049 P1 5 0.757600 0.333534 0.611715 11.00000 0.04426 0.05239 = 0.05649 -0.00396 0.00191 0.00173 CU1 6 0.235993 0.280589 0.393304 11.00000 0.05324 0.04000 = 0.03017 -0.00321 0.00550 0.00176 BR12 7 0.494692 0.092087 0.554193 11.00000 0.08020 0.05742 = 0.06355 0.01203 -0.00286 -0.00271 BR42 7 -0.020453 0.506112 0.373900 11.00000 0.08826 0.05439 = 0.11324 0.01646 0.01168 0.00380 BR52 7 0.177452 0.041909 0.388134 11.00000 0.12782 0.05401 = 0.09226 -0.02009 0.02487 0.00055 BR82 7 0.247542 0.468182 0.203639 11.00000 0.11730 0.06746 = 0.05986 0.01571 -0.00806 -0.00146 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_18120_1_0m_a.res in P2(1)/c REM R1 = 0.0872 for 4230 Fo > 4sig(Fo) and 0.1364 for all 6586 data REM 434 parameters refined using 0 restraints END WGHT 0.0705 5.8897 REM Instructions for potential hydrogen bonds HTAB C2 F5 HTAB C2 F3_$1 HTAB C43 Br52_$2 REM Highest difference peak 1.269, deepest hole -0.666, 1-sigma level 0.146 Q1 1 0.3628 0.4783 0.2197 11.00000 0.05 1.27 Q2 1 0.0653 0.0480 0.3727 11.00000 0.05 0.88 Q3 1 0.2403 0.0608 0.3614 11.00000 0.05 0.78 Q4 1 -0.0412 0.4877 0.3245 11.00000 0.05 0.68 Q5 1 0.3467 0.2798 0.4147 11.00000 0.05 0.67 ; _shelx_res_checksum 27577 loop_ _publcif_info_exptl_table_extra_item sin_theta_over_lambda_max loop_ _publcif_info_exptl_table_header_item ? _publcif_funding_html ; ;