#------------------------------------------------------------------------------ #$Date: 2023-11-08 04:20:43 +0200 (Wed, 08 Nov 2023) $ #$Revision: 287484 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247684.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_7247684 loop_ _publ_author_name 'Bensalah, Donia' 'Mansour, Lamjed' 'Sauthier, Mathieu' 'Gurbuz, Nevin' '\"Ozdemir, Ismail' 'Beji, Lotfi' 'Gatri, Rafik' 'Hamdi, Naceur' _publ_section_title ; Plausible PEPPSI catalysts for direct C--H functionalization of five-membered heterocyclic bioactive motifs: synthesis, spectral, X-ray crystallographic characterizations and catalytic activity ; _journal_issue 45 _journal_name_full 'RSC Advances' _journal_page_first 31386 _journal_page_last 31410 _journal_paper_doi 10.1039/D3RA06334H _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C31 H40 Br2 N4 O Pd' _chemical_formula_sum 'C31 H40 Br2 N4 O Pd' _chemical_formula_weight 750.89 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2023-09-12 deposited with the CCDC. 2023-11-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.464(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 24.7681(12) _cell_length_b 15.3486(11) _cell_length_c 17.0756(11) _cell_measurement_reflns_used 2380 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.92 _cell_measurement_theta_min 1.54 _cell_volume 6383.4(7) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material 'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXL-2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation '0.8 mm diameter, multiple pinhole' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_unetI/netI 0.0710 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 23981 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.827 _diffrn_reflns_theta_min 1.568 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 3.115 _exptl_absorpt_correction_T_max 0.6781 _exptl_absorpt_correction_T_min 0.3240 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.563 _exptl_crystal_description prism _exptl_crystal_F_000 3024 _exptl_crystal_size_max 0.610 _exptl_crystal_size_mid 0.360 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.692 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 358 _refine_ls_number_reflns 6796 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.933 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0366P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.0981 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3840 _reflns_number_total 6796 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06334h2.cif _cod_data_source_block db24 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7247684 _shelx_shelxl_version_number 2019/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.252 _shelx_estimated_absorpt_t_max 0.670 _shelx_res_file ; TITL db24 shelx.res created by SHELXL-2019/3 at 19:16:50 on 12-Sep-2023 CELL 0.71073 24.7681 15.3486 17.0756 90.000 100.464 90.000 ZERR 8.00 0.0012 0.0011 0.0011 0.000 0.004 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H BR N O PD UNIT 248 320 16 32 8 8 MERG 2 FMAP 2 PLAN 3 SIZE 0.140 0.360 0.610 ACTA BOND $H CONF L.S. 20 TEMP 23.00 WGHT 0.036600 FVAR 0.10111 PD1 6 0.714992 0.491602 0.623454 11.00000 0.04290 0.03585 = 0.04179 -0.00053 0.00536 0.00831 BR1 3 0.716939 0.491978 0.766918 11.00000 0.07838 0.06063 = 0.04381 0.00058 0.00947 0.01624 BR2 3 0.719940 0.503337 0.482012 11.00000 0.06590 0.05599 = 0.04592 -0.00406 0.01375 0.00209 O1 5 0.949424 0.615027 0.637624 11.00000 0.06380 0.10188 = 0.11512 0.00263 0.02827 0.02440 N1 4 0.701668 0.683396 0.610126 11.00000 0.02939 0.03689 = 0.05025 0.00055 0.00164 0.00023 N2 4 0.623492 0.619468 0.615049 11.00000 0.03660 0.03113 = 0.05195 -0.00514 0.00769 0.00287 N3 4 0.854748 0.681561 0.690482 11.00000 0.03647 0.05590 = 0.05367 0.00230 -0.00048 0.00158 N4 4 0.753875 0.369492 0.632260 11.00000 0.05357 0.03941 = 0.05009 0.00164 0.01070 0.01154 C1 1 0.677743 0.604579 0.615671 11.00000 0.03502 0.04476 = 0.03446 0.00128 0.00099 0.00693 C2 1 0.662788 0.749692 0.606178 11.00000 0.03952 0.03701 = 0.04076 -0.00039 -0.00352 0.00095 C3 1 0.667023 0.839712 0.598246 11.00000 0.04728 0.03986 = 0.05589 0.00112 -0.00009 -0.00357 AFIX 43 H3 2 0.700609 0.865895 0.596253 11.00000 -1.20000 AFIX 0 C4 1 0.619457 0.889178 0.593405 11.00000 0.06072 0.03339 = 0.06616 -0.00418 -0.00356 0.00512 C5 1 0.623356 0.987129 0.581027 11.00000 0.08716 0.03711 = 0.11999 -0.00188 -0.00219 0.00814 AFIX 137 H5A 2 0.613006 1.017259 0.625304 11.00000 -1.50000 H5B 2 0.599131 1.003607 0.532843 11.00000 -1.50000 H5C 2 0.660388 1.002235 0.577135 11.00000 -1.50000 AFIX 0 C6 1 0.568924 0.848235 0.598377 11.00000 0.05248 0.04290 = 0.08681 -0.00786 -0.00150 0.01520 C7 1 0.516537 0.902364 0.592909 11.00000 0.05467 0.05845 = 0.18656 -0.01100 -0.00779 0.02128 AFIX 137 H7A 2 0.488640 0.867995 0.610519 11.00000 -1.50000 H7B 2 0.504064 0.920042 0.538714 11.00000 -1.50000 H7C 2 0.524020 0.953037 0.626062 11.00000 -1.50000 AFIX 0 C8 1 0.565269 0.758523 0.605319 11.00000 0.03322 0.04535 = 0.08844 -0.00657 0.00113 0.00550 AFIX 43 H8 2 0.531887 0.731623 0.607225 11.00000 -1.20000 AFIX 0 C9 1 0.613479 0.709712 0.609368 11.00000 0.03972 0.03218 = 0.04688 -0.00011 -0.00209 0.00484 C10 1 0.760267 0.695764 0.605672 11.00000 0.03776 0.04417 = 0.04578 -0.00004 0.00639 -0.00008 AFIX 23 H10A 2 0.764066 0.747713 0.574780 11.00000 -1.20000 H10B 2 0.772724 0.646511 0.578110 11.00000 -1.20000 AFIX 0 C11 1 0.796911 0.704593 0.688143 11.00000 0.04353 0.06207 = 0.04326 -0.00995 0.00042 -0.00066 AFIX 23 H11A 2 0.795101 0.764299 0.706107 11.00000 -1.20000 H11B 2 0.782282 0.667575 0.725330 11.00000 -1.20000 AFIX 0 C12 1 0.863459 0.589157 0.685195 11.00000 0.05606 0.05928 = 0.09315 0.01208 0.00156 0.00303 AFIX 23 H12A 2 0.845007 0.567730 0.633823 11.00000 -1.20000 H12B 2 0.848315 0.559210 0.726324 11.00000 -1.20000 AFIX 0 C13 1 0.925660 0.570900 0.695640 11.00000 0.05830 0.07716 = 0.13672 0.01617 -0.00245 0.02320 AFIX 23 H13A 2 0.943514 0.589472 0.748299 11.00000 -1.20000 H13B 2 0.931581 0.508739 0.691398 11.00000 -1.20000 AFIX 0 C14 1 0.940541 0.704745 0.641990 11.00000 0.04924 0.09858 = 0.09499 0.01394 0.02141 -0.00174 AFIX 23 H14A 2 0.956360 0.733933 0.601107 11.00000 -1.20000 H14B 2 0.959085 0.726148 0.693321 11.00000 -1.20000 AFIX 0 C15 1 0.879574 0.727221 0.631168 11.00000 0.04571 0.06185 = 0.06682 0.00532 0.01162 -0.00438 AFIX 23 H15A 2 0.875194 0.789580 0.636802 11.00000 -1.20000 H15B 2 0.861294 0.710494 0.578176 11.00000 -1.20000 AFIX 0 C16 1 0.581287 0.553240 0.622172 11.00000 0.04444 0.03949 = 0.06508 0.00587 0.01644 -0.00318 AFIX 23 H16A 2 0.545553 0.581099 0.611337 11.00000 -1.20000 H16B 2 0.587230 0.532798 0.676817 11.00000 -1.20000 AFIX 0 C17 1 0.579963 0.474358 0.567400 11.00000 0.03180 0.03869 = 0.05098 0.00173 0.00439 -0.00186 C18 1 0.583091 0.389829 0.601595 11.00000 0.03759 0.04343 = 0.04524 0.00924 0.00689 -0.00285 C19 1 0.584625 0.375024 0.689573 11.00000 0.07653 0.05597 = 0.06437 0.01098 0.00728 -0.00680 AFIX 137 H19A 2 0.586836 0.313679 0.700658 11.00000 -1.50000 H19B 2 0.551876 0.398247 0.704246 11.00000 -1.50000 H19C 2 0.616138 0.403753 0.719636 11.00000 -1.50000 AFIX 0 C20 1 0.582621 0.317989 0.550428 11.00000 0.04208 0.03979 = 0.06770 -0.00007 0.00722 -0.00230 C21 1 0.587703 0.224764 0.582746 11.00000 0.06715 0.04330 = 0.10075 0.00649 0.01733 0.00062 AFIX 137 H21A 2 0.553720 0.207658 0.597766 11.00000 -1.50000 H21B 2 0.616669 0.222090 0.628428 11.00000 -1.50000 H21C 2 0.595908 0.186071 0.542314 11.00000 -1.50000 AFIX 0 C22 1 0.578770 0.331467 0.469685 11.00000 0.04019 0.05499 = 0.06363 -0.01187 0.00703 -0.00361 AFIX 43 H22 2 0.579480 0.283340 0.436797 11.00000 -1.20000 AFIX 0 C23 1 0.573885 0.413749 0.435494 11.00000 0.03231 0.06308 = 0.04323 -0.00174 0.00008 -0.00548 C24 1 0.569259 0.422755 0.345399 11.00000 0.06553 0.08299 = 0.05140 -0.00100 0.00784 -0.00335 AFIX 137 H24A 2 0.537673 0.457404 0.324391 11.00000 -1.50000 H24B 2 0.565515 0.366050 0.321298 11.00000 -1.50000 H24C 2 0.601682 0.450470 0.333907 11.00000 -1.50000 AFIX 0 C25 1 0.573475 0.486368 0.484885 11.00000 0.03208 0.04893 = 0.04935 0.00883 0.00071 -0.00146 C26 1 0.566941 0.576879 0.448857 11.00000 0.05899 0.05604 = 0.06185 0.01889 0.00556 -0.00753 AFIX 137 H26A 2 0.602470 0.602845 0.451299 11.00000 -1.50000 H26B 2 0.545480 0.612119 0.478137 11.00000 -1.50000 H26C 2 0.548736 0.572987 0.394319 11.00000 -1.50000 AFIX 0 C27 1 0.728933 0.301690 0.593530 11.00000 0.04967 0.04599 = 0.08732 -0.00900 0.00717 0.00478 AFIX 43 H27 2 0.695125 0.310127 0.560471 11.00000 -1.20000 AFIX 0 C28 1 0.751202 0.218866 0.600337 11.00000 0.07642 0.04380 = 0.11371 -0.01196 0.02890 -0.00076 AFIX 43 H28 2 0.731883 0.172432 0.573686 11.00000 -1.20000 AFIX 0 C29 1 0.801297 0.205542 0.645990 11.00000 0.08664 0.04414 = 0.09159 0.01445 0.02925 0.02270 AFIX 43 H29 2 0.817455 0.150648 0.649520 11.00000 -1.20000 AFIX 0 C30 1 0.827521 0.274826 0.686762 11.00000 0.07026 0.07018 = 0.07674 0.01285 -0.00117 0.03060 AFIX 43 H30 2 0.861683 0.267686 0.719228 11.00000 -1.20000 AFIX 0 C31 1 0.802466 0.355427 0.678930 11.00000 0.06747 0.05122 = 0.07108 -0.00141 -0.00997 0.01972 AFIX 43 H31 2 0.820227 0.402052 0.707445 11.00000 -1.20000 AFIX 0 HKLF 4 REM db24 REM wR2 = 0.0981, GooF = S = 0.933, Restrained GooF = 0.933 for all data REM R1 = 0.0487 for 3840 Fo > 4sig(Fo) and 0.1082 for all 6796 data REM 358 parameters refined using 0 restraints END WGHT 0.0366 0.0000 REM Highest difference peak 0.692, deepest hole -0.837, 1-sigma level 0.090 Q1 1 0.7089 0.5018 0.5494 11.00000 0.05 0.69 Q2 1 0.7191 0.4928 0.6981 11.00000 0.05 0.64 Q3 1 0.6693 0.5146 0.6545 11.00000 0.05 0.45 ; _shelx_res_checksum 83621 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 Pd1 Pd 0.71499(2) 0.49160(2) 0.62345(2) 0.04047(11) Uani 1 1 d . . . . . Br1 Br 0.71694(2) 0.49198(4) 0.76692(3) 0.06114(16) Uani 1 1 d . . . . . Br2 Br 0.71994(2) 0.50334(3) 0.48201(3) 0.05549(15) Uani 1 1 d . . . . . O1 O 0.94942(18) 0.6150(3) 0.6376(3) 0.0921(15) Uani 1 1 d . . . . . N1 N 0.70167(14) 0.6834(2) 0.6101(2) 0.0395(9) Uani 1 1 d . . . . . N2 N 0.62349(14) 0.6195(2) 0.6150(2) 0.0399(9) Uani 1 1 d . . . . . N3 N 0.85475(15) 0.6816(3) 0.6905(3) 0.0498(11) Uani 1 1 d . . . . . N4 N 0.75388(16) 0.3695(2) 0.6323(3) 0.0475(11) Uani 1 1 d . . . . . C1 C 0.67774(17) 0.6046(3) 0.6157(3) 0.0387(11) Uani 1 1 d . . . . . C2 C 0.66279(18) 0.7497(3) 0.6062(3) 0.0404(11) Uani 1 1 d . . . . . C3 C 0.6670(2) 0.8397(3) 0.5982(3) 0.0489(13) Uani 1 1 d . . . . . H3 H 0.700609 0.865895 0.596253 0.059 Uiso 1 1 calc R U . . . C4 C 0.6195(2) 0.8892(3) 0.5934(4) 0.0553(15) Uani 1 1 d . . . . . C5 C 0.6234(3) 0.9871(3) 0.5810(5) 0.084(2) Uani 1 1 d . . . . . H5A H 0.613006 1.017259 0.625304 0.126 Uiso 1 1 calc R U . . . H5B H 0.599131 1.003607 0.532843 0.126 Uiso 1 1 calc R U . . . H5C H 0.660388 1.002235 0.577135 0.126 Uiso 1 1 calc R U . . . C6 C 0.5689(2) 0.8482(3) 0.5984(4) 0.0625(16) Uani 1 1 d . . . . . C7 C 0.5165(2) 0.9024(4) 0.5929(5) 0.104(3) Uani 1 1 d . . . . . H7A H 0.488640 0.867995 0.610519 0.155 Uiso 1 1 calc R U . . . H7B H 0.504064 0.920042 0.538714 0.155 Uiso 1 1 calc R U . . . H7C H 0.524020 0.953037 0.626062 0.155 Uiso 1 1 calc R U . . . C8 C 0.5653(2) 0.7585(3) 0.6053(4) 0.0569(15) Uani 1 1 d . . . . . H8 H 0.531887 0.731623 0.607225 0.068 Uiso 1 1 calc R U . . . C9 C 0.61348(18) 0.7097(3) 0.6094(3) 0.0408(11) Uani 1 1 d . . . . . C10 C 0.76027(17) 0.6958(3) 0.6057(3) 0.0427(12) Uani 1 1 d . . . . . H10A H 0.764066 0.747713 0.574780 0.051 Uiso 1 1 calc R U . . . H10B H 0.772724 0.646511 0.578110 0.051 Uiso 1 1 calc R U . . . C11 C 0.79691(19) 0.7046(3) 0.6881(3) 0.0506(13) Uani 1 1 d . . . . . H11A H 0.795101 0.764299 0.706107 0.061 Uiso 1 1 calc R U . . . H11B H 0.782282 0.667575 0.725330 0.061 Uiso 1 1 calc R U . . . C12 C 0.8635(2) 0.5892(4) 0.6852(4) 0.0710(18) Uani 1 1 d . . . . . H12A H 0.845007 0.567730 0.633823 0.085 Uiso 1 1 calc R U . . . H12B H 0.848315 0.559210 0.726324 0.085 Uiso 1 1 calc R U . . . C13 C 0.9257(2) 0.5709(4) 0.6956(5) 0.093(2) Uani 1 1 d . . . . . H13A H 0.943514 0.589472 0.748299 0.112 Uiso 1 1 calc R U . . . H13B H 0.931581 0.508739 0.691398 0.112 Uiso 1 1 calc R U . . . C14 C 0.9405(2) 0.7047(5) 0.6420(5) 0.080(2) Uani 1 1 d . . . . . H14A H 0.956360 0.733933 0.601107 0.096 Uiso 1 1 calc R U . . . H14B H 0.959085 0.726148 0.693321 0.096 Uiso 1 1 calc R U . . . C15 C 0.8796(2) 0.7272(4) 0.6312(4) 0.0579(14) Uani 1 1 d . . . . . H15A H 0.875194 0.789580 0.636802 0.070 Uiso 1 1 calc R U . . . H15B H 0.861294 0.710494 0.578176 0.070 Uiso 1 1 calc R U . . . C16 C 0.5813(2) 0.5532(3) 0.6222(4) 0.0489(13) Uani 1 1 d . . . . . H16A H 0.545553 0.581099 0.611337 0.059 Uiso 1 1 calc R U . . . H16B H 0.587230 0.532798 0.676817 0.059 Uiso 1 1 calc R U . . . C17 C 0.57996(17) 0.4744(3) 0.5674(3) 0.0409(11) Uani 1 1 d . . . . . C18 C 0.58309(18) 0.3898(3) 0.6016(3) 0.0422(12) Uani 1 1 d . . . . . C19 C 0.5846(2) 0.3750(4) 0.6896(4) 0.0663(16) Uani 1 1 d . . . . . H19A H 0.586836 0.313679 0.700658 0.099 Uiso 1 1 calc R U . . . H19B H 0.551876 0.398247 0.704246 0.099 Uiso 1 1 calc R U . . . H19C H 0.616138 0.403753 0.719636 0.099 Uiso 1 1 calc R U . . . C20 C 0.58262(19) 0.3180(3) 0.5504(4) 0.0502(13) Uani 1 1 d . . . . . C21 C 0.5877(2) 0.2248(3) 0.5827(4) 0.0701(18) Uani 1 1 d . . . . . H21A H 0.553720 0.207658 0.597766 0.105 Uiso 1 1 calc R U . . . H21B H 0.616669 0.222090 0.628428 0.105 Uiso 1 1 calc R U . . . H21C H 0.595908 0.186071 0.542314 0.105 Uiso 1 1 calc R U . . . C22 C 0.57877(19) 0.3315(3) 0.4697(4) 0.0532(14) Uani 1 1 d . . . . . H22 H 0.579480 0.283340 0.436797 0.064 Uiso 1 1 calc R U . . . C23 C 0.57388(19) 0.4137(3) 0.4355(3) 0.0471(13) Uani 1 1 d . . . . . C24 C 0.5693(2) 0.4228(4) 0.3454(4) 0.0670(16) Uani 1 1 d . . . . . H24A H 0.537673 0.457404 0.324391 0.100 Uiso 1 1 calc R U . . . H24B H 0.565515 0.366050 0.321298 0.100 Uiso 1 1 calc R U . . . H24C H 0.601682 0.450470 0.333907 0.100 Uiso 1 1 calc R U . . . C25 C 0.57347(16) 0.4864(3) 0.4849(3) 0.0443(11) Uani 1 1 d . . . . . C26 C 0.5669(2) 0.5769(3) 0.4489(4) 0.0596(16) Uani 1 1 d . . . . . H26A H 0.602470 0.602845 0.451299 0.089 Uiso 1 1 calc R U . . . H26B H 0.545480 0.612119 0.478137 0.089 Uiso 1 1 calc R U . . . H26C H 0.548736 0.572987 0.394319 0.089 Uiso 1 1 calc R U . . . C27 C 0.7289(2) 0.3017(3) 0.5935(4) 0.0617(16) Uani 1 1 d . . . . . H27 H 0.695125 0.310127 0.560471 0.074 Uiso 1 1 calc R U . . . C28 C 0.7512(3) 0.2189(4) 0.6003(5) 0.077(2) Uani 1 1 d . . . . . H28 H 0.731883 0.172432 0.573686 0.092 Uiso 1 1 calc R U . . . C29 C 0.8013(3) 0.2055(4) 0.6460(4) 0.0725(18) Uani 1 1 d . . . . . H29 H 0.817455 0.150648 0.649520 0.087 Uiso 1 1 calc R U . . . C30 C 0.8275(3) 0.2748(4) 0.6868(4) 0.0742(18) Uani 1 1 d . . . . . H30 H 0.861683 0.267686 0.719228 0.089 Uiso 1 1 calc R U . . . C31 C 0.8025(2) 0.3554(3) 0.6789(4) 0.0661(17) Uani 1 1 d . . . . . H31 H 0.820227 0.402052 0.707445 0.079 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.04290(19) 0.03585(19) 0.0418(2) -0.00053(19) 0.00536(15) 0.00831(17) Br1 0.0784(4) 0.0606(3) 0.0438(3) 0.0006(3) 0.0095(3) 0.0162(3) Br2 0.0659(3) 0.0560(3) 0.0459(3) -0.0041(3) 0.0137(3) 0.0021(3) O1 0.064(3) 0.102(4) 0.115(4) 0.003(3) 0.028(3) 0.024(3) N1 0.0294(19) 0.0369(19) 0.050(3) 0.0006(18) 0.0016(18) 0.0002(15) N2 0.037(2) 0.0311(18) 0.052(3) -0.0051(18) 0.0077(19) 0.0029(15) N3 0.036(2) 0.056(2) 0.054(3) 0.002(2) 0.000(2) 0.0016(19) N4 0.054(3) 0.039(2) 0.050(3) 0.002(2) 0.011(2) 0.0115(19) C1 0.035(2) 0.045(2) 0.034(3) 0.001(2) 0.001(2) 0.007(2) C2 0.040(3) 0.037(2) 0.041(3) 0.000(2) -0.004(2) 0.0010(19) C3 0.047(3) 0.040(2) 0.056(4) 0.001(2) 0.000(3) -0.004(2) C4 0.061(3) 0.033(2) 0.066(4) -0.004(2) -0.004(3) 0.005(2) C5 0.087(4) 0.037(3) 0.120(6) -0.002(3) -0.002(4) 0.008(3) C6 0.052(3) 0.043(3) 0.087(5) -0.008(3) -0.002(3) 0.015(2) C7 0.055(4) 0.058(4) 0.187(9) -0.011(4) -0.008(4) 0.021(3) C8 0.033(3) 0.045(3) 0.088(5) -0.007(3) 0.001(3) 0.006(2) C9 0.040(2) 0.032(2) 0.047(3) 0.000(2) -0.002(2) 0.0048(19) C10 0.038(3) 0.044(3) 0.046(3) 0.000(2) 0.006(2) 0.000(2) C11 0.044(3) 0.062(3) 0.043(3) -0.010(3) 0.000(2) -0.001(2) C12 0.056(3) 0.059(3) 0.093(5) 0.012(3) 0.002(3) 0.003(3) C13 0.058(4) 0.077(4) 0.137(8) 0.016(5) -0.002(4) 0.023(3) C14 0.049(3) 0.099(5) 0.095(6) 0.014(4) 0.021(4) -0.002(3) C15 0.046(3) 0.062(3) 0.067(4) 0.005(3) 0.012(3) -0.004(2) C16 0.044(3) 0.039(2) 0.065(4) 0.006(2) 0.016(3) -0.003(2) C17 0.032(2) 0.039(2) 0.051(3) 0.002(2) 0.004(2) -0.0019(18) C18 0.038(3) 0.043(3) 0.045(3) 0.009(2) 0.007(2) -0.003(2) C19 0.077(4) 0.056(3) 0.064(4) 0.011(3) 0.007(3) -0.007(3) C20 0.042(3) 0.040(3) 0.068(4) 0.000(3) 0.007(3) -0.002(2) C21 0.067(4) 0.043(3) 0.101(6) 0.006(3) 0.017(4) 0.001(3) C22 0.040(3) 0.055(3) 0.064(4) -0.012(3) 0.007(3) -0.004(2) C23 0.032(3) 0.063(3) 0.043(3) -0.002(3) 0.000(2) -0.005(2) C24 0.066(4) 0.083(4) 0.051(4) -0.001(3) 0.008(3) -0.003(3) C25 0.032(2) 0.049(3) 0.049(3) 0.009(3) 0.001(2) -0.001(2) C26 0.059(3) 0.056(3) 0.062(4) 0.019(3) 0.006(3) -0.008(3) C27 0.050(3) 0.046(3) 0.087(5) -0.009(3) 0.007(3) 0.005(2) C28 0.076(4) 0.044(3) 0.114(6) -0.012(3) 0.029(4) -0.001(3) C29 0.087(4) 0.044(3) 0.092(5) 0.014(3) 0.029(4) 0.023(3) C30 0.070(4) 0.070(4) 0.077(5) 0.013(4) -0.001(4) 0.031(3) C31 0.067(4) 0.051(3) 0.071(4) -0.001(3) -0.010(3) 0.020(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Br Br -0.2901 2.4595 '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' Pd Pd -0.9988 1.0072 '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 C1 Pd1 N4 179.12(17) . . ? C1 Pd1 Br1 89.38(14) . . ? N4 Pd1 Br1 90.29(12) . . ? C1 Pd1 Br2 88.58(14) . . ? N4 Pd1 Br2 91.82(12) . . ? Br1 Pd1 Br2 174.13(3) . . ? C14 O1 C13 110.2(5) . . ? C1 N1 C2 110.3(3) . . ? C1 N1 C10 124.2(4) . . ? C2 N1 C10 125.4(4) . . ? C1 N2 C9 109.1(4) . . ? C1 N2 C16 126.5(4) . . ? C9 N2 C16 124.3(4) . . ? C12 N3 C15 110.1(5) . . ? C12 N3 C11 113.1(4) . . ? C15 N3 C11 113.5(4) . . ? C27 N4 C31 117.3(4) . . ? C27 N4 Pd1 120.0(3) . . ? C31 N4 Pd1 122.6(3) . . ? N1 C1 N2 107.0(4) . . ? N1 C1 Pd1 126.0(3) . . ? N2 C1 Pd1 127.0(3) . . ? C9 C2 C3 121.9(4) . . ? C9 C2 N1 106.4(4) . . ? C3 C2 N1 131.6(4) . . ? C4 C3 C2 118.0(5) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C6 120.1(4) . . ? C3 C4 C5 118.2(5) . . ? C6 C4 C5 121.7(5) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C6 C4 121.2(5) . . ? C8 C6 C7 118.5(5) . . ? C4 C6 C7 120.3(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C9 117.8(5) . . ? C6 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? C2 C9 C8 120.9(4) . . ? C2 C9 N2 107.2(4) . . ? C8 C9 N2 131.9(4) . . ? N1 C10 C11 112.7(4) . . ? N1 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? N1 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N3 C11 C10 114.5(4) . . ? N3 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? N3 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? N3 C12 C13 109.2(5) . . ? N3 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? N3 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? O1 C13 C12 111.5(5) . . ? O1 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? O1 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? O1 C14 C15 112.2(5) . . ? O1 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? O1 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N3 C15 C14 109.9(5) . . ? N3 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? N3 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C17 115.6(4) . . ? N2 C16 H16A 108.4 . . ? C17 C16 H16A 108.4 . . ? N2 C16 H16B 108.4 . . ? C17 C16 H16B 108.4 . . ? H16A C16 H16B 107.4 . . ? C25 C17 C18 121.5(4) . . ? C25 C17 C16 119.8(4) . . ? C18 C17 C16 118.7(4) . . ? C20 C18 C17 117.9(5) . . ? C20 C18 C19 119.7(4) . . ? C17 C18 C19 122.4(5) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C20 C18 119.6(5) . . ? C22 C20 C21 119.1(5) . . ? C18 C20 C21 121.2(5) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 C23 122.8(5) . . ? C20 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C25 118.8(5) . . ? C22 C23 C24 119.4(5) . . ? C25 C23 C24 121.8(5) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 C17 119.3(4) . . ? C23 C25 C26 119.8(5) . . ? C17 C25 C26 120.9(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N4 C27 C28 122.5(5) . . ? N4 C27 H27 118.7 . . ? C28 C27 H27 118.7 . . ? C29 C28 C27 119.8(6) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 118.4(5) . . ? C28 C29 H29 120.8 . . ? C30 C29 H29 120.8 . . ? C29 C30 C31 118.9(6) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? N4 C31 C30 122.9(6) . . ? N4 C31 H31 118.5 . . ? C30 C31 H31 118.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.957(4) . ? Pd1 N4 2.100(4) . ? Pd1 Br1 2.4414(7) . ? Pd1 Br2 2.4471(7) . ? O1 C14 1.399(8) . ? O1 C13 1.414(8) . ? N1 C1 1.358(5) . ? N1 C2 1.394(5) . ? N1 C10 1.479(5) . ? N2 C1 1.361(5) . ? N2 C9 1.407(5) . ? N2 C16 1.479(5) . ? N3 C12 1.440(7) . ? N3 C15 1.456(7) . ? N3 C11 1.469(6) . ? N4 C27 1.324(6) . ? N4 C31 1.335(6) . ? C2 C9 1.377(6) . ? C2 C3 1.394(6) . ? C3 C4 1.391(7) . ? C3 H3 0.9300 . ? C4 C6 1.417(7) . ? C4 C5 1.524(7) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C8 1.386(7) . ? C6 C7 1.529(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.401(6) . ? C8 H8 0.9300 . ? C10 C11 1.537(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.544(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.527(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.527(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C25 1.401(7) . ? C17 C18 1.419(6) . ? C18 C20 1.406(7) . ? C18 C19 1.513(8) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C22 1.380(8) . ? C20 C21 1.531(7) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.387(7) . ? C22 H22 0.9300 . ? C23 C25 1.399(7) . ? C23 C24 1.528(8) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.516(6) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.382(7) . ? C27 H27 0.9300 . ? C28 C29 1.356(9) . ? C28 H28 0.9300 . ? C29 C30 1.369(9) . ? C29 H29 0.9300 . ? C30 C31 1.380(7) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 0.2(5) . . . . ? C10 N1 C1 N2 -177.5(4) . . . . ? C2 N1 C1 Pd1 -179.6(3) . . . . ? C10 N1 C1 Pd1 2.7(7) . . . . ? C9 N2 C1 N1 -0.3(5) . . . . ? C16 N2 C1 N1 -178.1(4) . . . . ? C9 N2 C1 Pd1 179.5(4) . . . . ? C16 N2 C1 Pd1 1.6(7) . . . . ? C1 N1 C2 C9 -0.1(6) . . . . ? C10 N1 C2 C9 177.6(4) . . . . ? C1 N1 C2 C3 -178.3(5) . . . . ? C10 N1 C2 C3 -0.6(9) . . . . ? C9 C2 C3 C4 -0.1(8) . . . . ? N1 C2 C3 C4 177.9(5) . . . . ? C2 C3 C4 C6 1.4(8) . . . . ? C2 C3 C4 C5 -177.3(5) . . . . ? C3 C4 C6 C8 -2.3(10) . . . . ? C5 C4 C6 C8 176.5(6) . . . . ? C3 C4 C6 C7 -179.9(6) . . . . ? C5 C4 C6 C7 -1.2(10) . . . . ? C4 C6 C8 C9 1.6(10) . . . . ? C7 C6 C8 C9 179.3(6) . . . . ? C3 C2 C9 C8 -0.5(8) . . . . ? N1 C2 C9 C8 -178.9(5) . . . . ? C3 C2 C9 N2 178.3(5) . . . . ? N1 C2 C9 N2 -0.1(5) . . . . ? C6 C8 C9 C2 -0.3(9) . . . . ? C6 C8 C9 N2 -178.7(6) . . . . ? C1 N2 C9 C2 0.3(6) . . . . ? C16 N2 C9 C2 178.2(5) . . . . ? C1 N2 C9 C8 178.9(6) . . . . ? C16 N2 C9 C8 -3.2(9) . . . . ? C1 N1 C10 C11 -89.3(6) . . . . ? C2 N1 C10 C11 93.4(5) . . . . ? C12 N3 C11 C10 -73.6(6) . . . . ? C15 N3 C11 C10 52.7(6) . . . . ? N1 C10 C11 N3 156.3(4) . . . . ? C15 N3 C12 C13 56.9(7) . . . . ? C11 N3 C12 C13 -175.0(5) . . . . ? C14 O1 C13 C12 58.1(8) . . . . ? N3 C12 C13 O1 -58.3(8) . . . . ? C13 O1 C14 C15 -57.6(8) . . . . ? C12 N3 C15 C14 -56.5(6) . . . . ? C11 N3 C15 C14 175.7(5) . . . . ? O1 C14 C15 N3 57.0(8) . . . . ? C1 N2 C16 C17 -49.1(7) . . . . ? C9 N2 C16 C17 133.3(5) . . . . ? N2 C16 C17 C25 -56.3(6) . . . . ? N2 C16 C17 C18 126.3(5) . . . . ? C25 C17 C18 C20 3.6(7) . . . . ? C16 C17 C18 C20 -179.1(4) . . . . ? C25 C17 C18 C19 -174.0(4) . . . . ? C16 C17 C18 C19 3.3(7) . . . . ? C17 C18 C20 C22 -0.5(7) . . . . ? C19 C18 C20 C22 177.1(5) . . . . ? C17 C18 C20 C21 178.0(4) . . . . ? C19 C18 C20 C21 -4.3(7) . . . . ? C18 C20 C22 C23 -1.7(7) . . . . ? C21 C20 C22 C23 179.8(5) . . . . ? C20 C22 C23 C25 0.8(7) . . . . ? C20 C22 C23 C24 -179.4(5) . . . . ? C22 C23 C25 C17 2.3(6) . . . . ? C24 C23 C25 C17 -177.6(4) . . . . ? C22 C23 C25 C26 -178.7(4) . . . . ? C24 C23 C25 C26 1.5(7) . . . . ? C18 C17 C25 C23 -4.5(6) . . . . ? C16 C17 C25 C23 178.2(4) . . . . ? C18 C17 C25 C26 176.5(4) . . . . ? C16 C17 C25 C26 -0.8(6) . . . . ? C31 N4 C27 C28 0.3(9) . . . . ? Pd1 N4 C27 C28 -176.5(5) . . . . ? N4 C27 C28 C29 -2.3(10) . . . . ? C27 C28 C29 C30 2.5(10) . . . . ? C28 C29 C30 C31 -1.0(10) . . . . ? C27 N4 C31 C30 1.3(9) . . . . ? Pd1 N4 C31 C30 178.1(5) . . . . ? C29 C30 C31 N4 -1.0(11) . . . . ?