#------------------------------------------------------------------------------ #$Date: 2021-11-06 20:30:40 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270345 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564765.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_1564765 loop_ _publ_author_name 'Prima, Darya O.' 'Madiyeva, Malena' 'Burykina, Julia V.' 'Minyaev, Mikhail E.' 'Boiko, Daniil A.' 'Ananikov, Valentine P.' _publ_section_title ; Evidence for “cocktail”-type catalysis in Buchwald--Hartwig reaction. A mechanistic study ; _journal_issue 21 _journal_name_full 'Catalysis Science & Technology' _journal_page_first 7171 _journal_page_last 7188 _journal_paper_doi 10.1039/D1CY01601F _journal_volume 11 _journal_year 2021 _chemical_formula_moiety 'C54 H72 Cl4 N4 Pd2, 2(C H2 Cl2)' _chemical_formula_sum 'C56 H76 Cl8 N4 Pd2' _chemical_formula_weight 1301.60 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-04-25 deposited with the CCDC. 2021-09-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.2641(3) _cell_length_b 19.0639(4) _cell_length_c 22.6150(5) _cell_measurement_reflns_used 9889 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 34.93 _cell_measurement_theta_min 2.32 _cell_volume 6149.7(2) _computing_cell_refinement 'SAINT (Bruker, 2019)' _computing_data_collection 'APEX3 (Bruker, 2019)' _computing_data_reduction 'SAINT (Bruker, 2019)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)' _computing_structure_refinement 'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)' _computing_structure_solution 'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker AXS D8 QUEST, Photon III detector' _diffrn_measurement_method '\f and \w shutterless scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0203 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 165577 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.648 _diffrn_reflns_theta_min 2.137 _diffrn_source 'sealed X-Ray tube' _diffrn_source_current 30 _diffrn_source_power 50 _diffrn_source_size '0.6 mm, fine-focus' _exptl_absorpt_coefficient_mu 0.970 _exptl_absorpt_correction_T_max 0.3859 _exptl_absorpt_correction_T_min 0.3093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)' _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2672 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.753 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 334 _refine_ls_number_reflns 13189 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0286 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0165P)^2^+5.2166P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.0628 _reflns_Friedel_coverage 0.000 _reflns_number_gt 10792 _reflns_number_total 13189 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cy01601f2.cif _cod_data_source_block 2a _cod_depositor_comments 'Adding full bibliography for 1564765--1564770.cif.' _cod_database_code 1564765 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.643 _shelx_estimated_absorpt_t_max 0.852 _shelx_res_file ; TITL MM3 in Pbca MM3.res created by SHELXL-2018/3 at 18:44:06 on 30-Nov-2020 CELL 0.71073 14.26410 19.06390 22.61500 90.0000 90.0000 90.0000 ZERR 4.00 0.00030 0.00040 0.00050 0.0000 0.0000 0.0000 LATT 1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N Cl Pd UNIT 224 304 16 32 8 TEMP -173.15 SIZE 0.17 0.20 0.50 OMIT -4 69.30 LIST 4 L.S. 10 FMAP 2 PLAN 15 ACTA HTAB BOND $H CONF SADI 0.003 C28A Cl3A C28B Cl3B SADI 0.003 C28A Cl4A C28B Cl4B EADP C28A C28B EADP Cl3A Cl3B EADP Cl4A Cl4B WGHT 0.016500 5.216600 FVAR 0.05643 0.83238 PD1 5 0.531200 0.586548 0.501375 11.00000 0.01009 0.01193 = 0.01362 0.00034 0.00080 -0.00086 CL1 4 0.603249 0.482838 0.473576 11.00000 0.01359 0.01394 = 0.03096 -0.00082 0.00669 -0.00117 CL2 4 0.457499 0.686029 0.531628 11.00000 0.01500 0.01561 = 0.02134 -0.00168 0.00139 0.00160 N1 3 0.699718 0.676963 0.517148 11.00000 0.01217 0.01675 = 0.01488 -0.00200 0.00034 -0.00229 C1 1 0.643273 0.639735 0.480470 11.00000 0.01225 0.01378 = 0.01374 -0.00023 0.00089 -0.00060 N2 3 0.684518 0.643648 0.426631 11.00000 0.01236 0.01586 = 0.01406 -0.00128 0.00136 -0.00219 C2 1 0.766535 0.682872 0.429886 11.00000 0.01446 0.02026 = 0.01872 -0.00243 0.00382 -0.00468 AFIX 43 H2 2 0.807833 0.693297 0.398123 11.00000 -1.20000 AFIX 0 C3 1 0.776372 0.703240 0.486384 11.00000 0.01372 0.02032 = 0.02057 -0.00392 0.00262 -0.00439 AFIX 43 H3 2 0.826194 0.730410 0.502276 11.00000 -1.20000 AFIX 0 C4 1 0.685800 0.694432 0.578707 11.00000 0.01406 0.01994 = 0.01423 -0.00328 0.00033 -0.00319 C5 1 0.708984 0.645013 0.621872 11.00000 0.01814 0.02265 = 0.01687 -0.00172 -0.00164 -0.00323 C6 1 0.706943 0.667344 0.680784 11.00000 0.02702 0.03238 = 0.01611 -0.00088 -0.00183 -0.00570 AFIX 43 H6 2 0.722892 0.635329 0.711363 11.00000 -1.20000 AFIX 0 C7 1 0.682058 0.735315 0.695142 11.00000 0.02952 0.03641 = 0.01709 -0.00924 0.00331 -0.00830 AFIX 43 H7 2 0.682288 0.749783 0.735339 11.00000 -1.20000 AFIX 0 C8 1 0.656804 0.782467 0.651409 11.00000 0.02338 0.02596 = 0.02524 -0.01048 0.00533 -0.00342 AFIX 43 H8 2 0.638418 0.828629 0.662173 11.00000 -1.20000 AFIX 0 C9 1 0.657829 0.763492 0.591770 11.00000 0.01478 0.01996 = 0.02087 -0.00538 0.00207 -0.00304 C10 1 0.737028 0.569954 0.607321 11.00000 0.02534 0.02231 = 0.02084 0.00128 -0.00416 0.00062 AFIX 13 H10 2 0.730222 0.563326 0.563668 11.00000 -1.20000 AFIX 0 C11 1 0.671565 0.517659 0.638085 11.00000 0.04517 0.02414 = 0.03436 0.00237 0.00535 -0.00500 AFIX 137 H11A 2 0.690649 0.469705 0.628143 11.00000 -1.50000 H11B 2 0.607028 0.525530 0.624786 11.00000 -1.50000 H11C 2 0.675166 0.524311 0.680995 11.00000 -1.50000 AFIX 0 C12 1 0.839762 0.556744 0.623407 11.00000 0.03061 0.03642 = 0.04320 -0.00389 -0.01134 0.00648 AFIX 137 H12A 2 0.856427 0.508262 0.613554 11.00000 -1.50000 H12B 2 0.848754 0.564499 0.665868 11.00000 -1.50000 H12C 2 0.879877 0.589013 0.601098 11.00000 -1.50000 AFIX 0 C13 1 0.630908 0.816188 0.544479 11.00000 0.02029 0.01777 = 0.02820 -0.00382 0.00137 0.00047 AFIX 13 H13 2 0.619246 0.789896 0.506930 11.00000 -1.20000 AFIX 0 C14 1 0.709970 0.869026 0.533095 11.00000 0.02639 0.02258 = 0.03942 0.00229 0.00571 -0.00157 AFIX 137 H14A 2 0.690423 0.902172 0.502352 11.00000 -1.50000 H14B 2 0.766281 0.843985 0.520026 11.00000 -1.50000 H14C 2 0.723720 0.894679 0.569632 11.00000 -1.50000 AFIX 0 C15 1 0.540854 0.855899 0.560533 11.00000 0.02223 0.02129 = 0.05081 -0.00613 0.00293 0.00313 AFIX 137 H15A 2 0.520697 0.884283 0.526715 11.00000 -1.50000 H15B 2 0.552857 0.886559 0.594482 11.00000 -1.50000 H15C 2 0.491498 0.822215 0.570656 11.00000 -1.50000 AFIX 0 C16 1 0.648306 0.617421 0.371156 11.00000 0.01570 0.01731 = 0.01353 -0.00032 0.00059 -0.00294 C17 1 0.696746 0.563085 0.342599 11.00000 0.01762 0.01959 = 0.01754 -0.00254 0.00163 -0.00183 C18 1 0.663341 0.542559 0.287268 11.00000 0.02698 0.02671 = 0.01928 -0.00668 0.00016 -0.00150 AFIX 43 H18 2 0.694666 0.506208 0.266405 11.00000 -1.20000 AFIX 0 C19 1 0.585846 0.573906 0.262231 11.00000 0.03030 0.03228 = 0.01861 -0.00423 -0.00522 -0.00412 AFIX 43 H19 2 0.564108 0.558559 0.224691 11.00000 -1.20000 AFIX 0 C20 1 0.539335 0.627615 0.291319 11.00000 0.02342 0.02955 = 0.01877 0.00218 -0.00472 -0.00172 AFIX 43 H20 2 0.486130 0.648758 0.273407 11.00000 -1.20000 AFIX 0 C21 1 0.569704 0.651096 0.346700 11.00000 0.01706 0.02119 = 0.01670 0.00305 0.00075 -0.00188 C22 1 0.784438 0.528712 0.367504 11.00000 0.01858 0.02515 = 0.02244 -0.00679 0.00094 0.00270 AFIX 13 H22 2 0.790960 0.543258 0.409789 11.00000 -1.20000 AFIX 0 C23 1 0.871732 0.553920 0.333874 11.00000 0.01971 0.03954 = 0.03413 -0.01023 0.00485 -0.00189 AFIX 137 H23A 2 0.927944 0.533429 0.351830 11.00000 -1.50000 H23B 2 0.875501 0.605192 0.335900 11.00000 -1.50000 H23C 2 0.867441 0.539220 0.292438 11.00000 -1.50000 AFIX 0 C24 1 0.780194 0.448343 0.365326 11.00000 0.03020 0.02626 = 0.03302 -0.00550 0.00283 0.00714 AFIX 137 H24A 2 0.836701 0.428815 0.383673 11.00000 -1.50000 H24B 2 0.776469 0.432869 0.324069 11.00000 -1.50000 H24C 2 0.724702 0.432005 0.386846 11.00000 -1.50000 AFIX 0 C25 1 0.522914 0.713067 0.376742 11.00000 0.02196 0.02431 = 0.01809 0.00437 0.00202 0.00544 AFIX 13 H25 2 0.528709 0.705749 0.420376 11.00000 -1.20000 AFIX 0 C26 1 0.418661 0.719601 0.362738 11.00000 0.02339 0.05495 = 0.03925 -0.00234 -0.00035 0.01284 AFIX 137 H26A 2 0.391016 0.756568 0.387289 11.00000 -1.50000 H26B 2 0.387361 0.674912 0.371039 11.00000 -1.50000 H26C 2 0.410632 0.731523 0.320891 11.00000 -1.50000 AFIX 0 C27 1 0.574579 0.781241 0.361760 11.00000 0.04241 0.02114 = 0.05785 0.00522 0.01553 0.00591 AFIX 137 H27A 2 0.546133 0.820247 0.383549 11.00000 -1.50000 H27B 2 0.569962 0.790235 0.319194 11.00000 -1.50000 H27C 2 0.640692 0.776852 0.372953 11.00000 -1.50000 AFIX 0 PART 1 21 CL3A 4 0.627891 0.290721 0.307136 21.00000 0.05036 0.06086 = 0.03503 0.00487 0.00811 0.01192 CL4A 4 0.505379 0.397442 0.257512 21.00000 0.04426 0.03927 = 0.02515 0.00603 -0.00284 -0.01353 C28A 1 0.541844 0.355258 0.322733 21.00000 0.02899 0.05001 = 0.01854 0.00003 -0.00159 -0.00234 AFIX 23 H28A 2 0.487184 0.332866 0.342007 21.00000 -1.20000 H28B 2 0.568046 0.390355 0.350444 21.00000 -1.20000 AFIX 0 PART 2 -21 CL3B 4 0.611812 0.270241 0.307145 -21.00000 0.05036 0.06086 = 0.03503 0.00487 0.00811 0.01192 CL4B 4 0.523060 0.398960 0.267466 -21.00000 0.04426 0.03927 = 0.02515 0.00603 -0.00284 -0.01353 C28B 1 0.550167 0.346662 0.329168 -21.00000 0.02899 0.05001 = 0.01854 0.00003 -0.00159 -0.00234 AFIX 23 H28C 2 0.491578 0.333027 0.349628 -21.00000 -1.20000 H28D 2 0.588996 0.373934 0.357240 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM MM3 in Pbca REM wR2 = 0.062779, GooF = S = 1.07500, Restrained GooF = 1.07492 for all data REM R1 = 0.028581 for 10792 Fo > 4sig(Fo) and 0.041073 for all 13189 data REM 334 parameters refined using 2 restraints END WGHT 0.0165 5.2166 REM Instructions for potential hydrogen bonds EQIV $2 -x+3/2, y+1/2, z HTAB C2 Cl3A_$2 HTAB C2 Cl3B_$2 EQIV $3 x+1/2, -y+3/2, -z+1 HTAB C3 Cl2_$3 REM Highest difference peak 0.753, deepest hole -0.751, 1-sigma level 0.077 Q1 1 0.5950 0.4134 0.5002 11.00000 0.05 0.75 Q2 1 0.4615 0.6870 0.4681 11.00000 0.05 0.70 Q3 1 0.4727 0.7600 0.4999 11.00000 0.05 0.66 Q4 1 0.6172 0.3134 0.2898 11.00000 0.05 0.53 Q5 1 0.6438 0.2606 0.2965 11.00000 0.05 0.52 Q6 1 0.7782 0.6899 0.4580 11.00000 0.05 0.49 Q7 1 0.6029 0.4827 0.5239 11.00000 0.05 0.48 Q8 1 0.5431 0.7759 0.3391 11.00000 0.05 0.47 Q9 1 0.6456 0.2987 0.3254 11.00000 0.05 0.46 Q10 1 0.6158 0.6368 0.3552 11.00000 0.05 0.45 Q11 1 0.6400 0.7902 0.5712 11.00000 0.05 0.44 Q12 1 0.7384 0.5487 0.3536 11.00000 0.05 0.43 Q13 1 0.6590 0.7715 0.6205 11.00000 0.05 0.43 Q14 1 0.6698 0.7259 0.5860 11.00000 0.05 0.43 Q15 1 0.6591 0.6379 0.4498 11.00000 0.05 0.42 ; _shelx_res_checksum 14354 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -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 0.53120(2) 0.58655(2) 0.50138(2) 0.01188(2) Uani 1 1 d . . . . . Cl1 Cl 0.60325(2) 0.48284(2) 0.47358(2) 0.01950(6) Uani 1 1 d . . . . . Cl2 Cl 0.45750(2) 0.68603(2) 0.53163(2) 0.01732(5) Uani 1 1 d . . . . . N1 N 0.69972(7) 0.67696(6) 0.51715(5) 0.01460(18) Uani 1 1 d . . . . . C1 C 0.64327(8) 0.63973(6) 0.48047(5) 0.01326(19) Uani 1 1 d . . . . . N2 N 0.68452(7) 0.64365(5) 0.42663(5) 0.01409(18) Uani 1 1 d . . . . . C2 C 0.76654(9) 0.68287(7) 0.42989(6) 0.0178(2) Uani 1 1 d . . . . . H2 H 0.807833 0.693297 0.398123 0.021 Uiso 1 1 calc R U . . . C3 C 0.77637(9) 0.70324(7) 0.48638(6) 0.0182(2) Uani 1 1 d . . . . . H3 H 0.826194 0.730410 0.502276 0.022 Uiso 1 1 calc R U . . . C4 C 0.68580(9) 0.69443(7) 0.57871(6) 0.0161(2) Uani 1 1 d . . . . . C5 C 0.70898(10) 0.64501(7) 0.62187(6) 0.0192(2) Uani 1 1 d . . . . . C6 C 0.70694(11) 0.66734(9) 0.68078(6) 0.0252(3) Uani 1 1 d . . . . . H6 H 0.722892 0.635329 0.711363 0.030 Uiso 1 1 calc R U . . . C7 C 0.68206(11) 0.73531(9) 0.69514(7) 0.0277(3) Uani 1 1 d . . . . . H7 H 0.682288 0.749783 0.735339 0.033 Uiso 1 1 calc R U . . . C8 C 0.65680(11) 0.78247(8) 0.65141(7) 0.0249(3) Uani 1 1 d . . . . . H8 H 0.638418 0.828629 0.662173 0.030 Uiso 1 1 calc R U . . . C9 C 0.65783(9) 0.76349(7) 0.59177(6) 0.0185(2) Uani 1 1 d . . . . . C10 C 0.73703(11) 0.56995(8) 0.60732(7) 0.0228(3) Uani 1 1 d . . . . . H10 H 0.730222 0.563326 0.563668 0.027 Uiso 1 1 calc R U . . . C11 C 0.67156(14) 0.51766(9) 0.63809(8) 0.0346(4) Uani 1 1 d . . . . . H11A H 0.690649 0.469705 0.628143 0.052 Uiso 1 1 calc R U . . . H11B H 0.607028 0.525530 0.624786 0.052 Uiso 1 1 calc R U . . . H11C H 0.675166 0.524311 0.680995 0.052 Uiso 1 1 calc R U . . . C12 C 0.83976(13) 0.55674(10) 0.62341(9) 0.0367(4) Uani 1 1 d . . . . . H12A H 0.856427 0.508262 0.613554 0.055 Uiso 1 1 calc R U . . . H12B H 0.848754 0.564499 0.665868 0.055 Uiso 1 1 calc R U . . . H12C H 0.879877 0.589013 0.601098 0.055 Uiso 1 1 calc R U . . . C13 C 0.63091(10) 0.81619(7) 0.54448(7) 0.0221(3) Uani 1 1 d . . . . . H13 H 0.619246 0.789896 0.506930 0.027 Uiso 1 1 calc R U . . . C14 C 0.70997(11) 0.86903(8) 0.53309(8) 0.0295(3) Uani 1 1 d . . . . . H14A H 0.690423 0.902172 0.502352 0.044 Uiso 1 1 calc R U . . . H14B H 0.766281 0.843985 0.520026 0.044 Uiso 1 1 calc R U . . . H14C H 0.723720 0.894679 0.569632 0.044 Uiso 1 1 calc R U . . . C15 C 0.54085(11) 0.85590(8) 0.56053(9) 0.0314(3) Uani 1 1 d . . . . . H15A H 0.520697 0.884283 0.526715 0.047 Uiso 1 1 calc R U . . . H15B H 0.552857 0.886559 0.594482 0.047 Uiso 1 1 calc R U . . . H15C H 0.491498 0.822215 0.570656 0.047 Uiso 1 1 calc R U . . . C16 C 0.64831(9) 0.61742(7) 0.37116(6) 0.0155(2) Uani 1 1 d . . . . . C17 C 0.69675(9) 0.56309(7) 0.34260(6) 0.0183(2) Uani 1 1 d . . . . . C18 C 0.66334(11) 0.54256(8) 0.28727(6) 0.0243(3) Uani 1 1 d . . . . . H18 H 0.694666 0.506208 0.266405 0.029 Uiso 1 1 calc R U . . . C19 C 0.58585(12) 0.57391(8) 0.26223(7) 0.0271(3) Uani 1 1 d . . . . . H19 H 0.564108 0.558559 0.224691 0.032 Uiso 1 1 calc R U . . . C20 C 0.53933(11) 0.62762(8) 0.29132(6) 0.0239(3) Uani 1 1 d . . . . . H20 H 0.486130 0.648758 0.273407 0.029 Uiso 1 1 calc R U . . . C21 C 0.56970(9) 0.65110(7) 0.34670(6) 0.0183(2) Uani 1 1 d . . . . . C22 C 0.78444(10) 0.52871(8) 0.36750(6) 0.0221(3) Uani 1 1 d . . . . . H22 H 0.790960 0.543258 0.409789 0.026 Uiso 1 1 calc R U . . . C23 C 0.87173(11) 0.55392(10) 0.33387(8) 0.0311(3) Uani 1 1 d . . . . . H23A H 0.927944 0.533429 0.351830 0.047 Uiso 1 1 calc R U . . . H23B H 0.875501 0.605192 0.335900 0.047 Uiso 1 1 calc R U . . . H23C H 0.867441 0.539220 0.292438 0.047 Uiso 1 1 calc R U . . . C24 C 0.78019(12) 0.44834(8) 0.36533(8) 0.0298(3) Uani 1 1 d . . . . . H24A H 0.836701 0.428815 0.383673 0.045 Uiso 1 1 calc R U . . . H24B H 0.776469 0.432869 0.324069 0.045 Uiso 1 1 calc R U . . . H24C H 0.724702 0.432005 0.386846 0.045 Uiso 1 1 calc R U . . . C25 C 0.52291(10) 0.71307(8) 0.37674(6) 0.0215(3) Uani 1 1 d . . . . . H25 H 0.528709 0.705749 0.420376 0.026 Uiso 1 1 calc R U . . . C26 C 0.41866(12) 0.71960(11) 0.36274(9) 0.0392(4) Uani 1 1 d . . . . . H26A H 0.391016 0.756568 0.387289 0.059 Uiso 1 1 calc R U . . . H26B H 0.387361 0.674912 0.371039 0.059 Uiso 1 1 calc R U . . . H26C H 0.410632 0.731523 0.320891 0.059 Uiso 1 1 calc R U . . . C27 C 0.57458(14) 0.78124(9) 0.36176(10) 0.0405(4) Uani 1 1 d . . . . . H27A H 0.546133 0.820247 0.383549 0.061 Uiso 1 1 calc R U . . . H27B H 0.569962 0.790235 0.319194 0.061 Uiso 1 1 calc R U . . . H27C H 0.640692 0.776852 0.372953 0.061 Uiso 1 1 calc R U . . . Cl3A Cl 0.62789(14) 0.29072(16) 0.30714(5) 0.0488(4) Uani 0.832(9) 1 d D . P A 1 Cl4A Cl 0.50538(15) 0.39744(6) 0.25751(8) 0.0362(2) Uani 0.832(9) 1 d D . P A 1 C28A C 0.5418(5) 0.3553(3) 0.32273(11) 0.0325(4) Uani 0.832(9) 1 d D . P A 1 H28A H 0.487184 0.332866 0.342007 0.039 Uiso 0.832(9) 1 calc R U P A 1 H28B H 0.568046 0.390355 0.350444 0.039 Uiso 0.832(9) 1 calc R U P A 1 Cl3B Cl 0.6118(6) 0.2702(5) 0.3071(3) 0.0488(4) Uani 0.168(9) 1 d D . P A 2 Cl4B Cl 0.5231(6) 0.3990(4) 0.2675(3) 0.0362(2) Uani 0.168(9) 1 d D . P A 2 C28B C 0.550(3) 0.3467(13) 0.3292(4) 0.0325(4) Uani 0.168(9) 1 d D . P A 2 H28C H 0.491578 0.333027 0.349628 0.039 Uiso 0.168(9) 1 calc R U P A 2 H28D H 0.588996 0.373934 0.357240 0.039 Uiso 0.168(9) 1 calc R U P A 2 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 0.01009(4) 0.01193(4) 0.01362(4) 0.00034(3) 0.00080(3) -0.00086(3) Cl1 0.01359(12) 0.01394(11) 0.03096(16) -0.00082(11) 0.00669(11) -0.00117(10) Cl2 0.01500(12) 0.01561(11) 0.02134(13) -0.00168(10) 0.00139(10) 0.00160(10) N1 0.0122(4) 0.0168(4) 0.0149(4) -0.0020(4) 0.0003(3) -0.0023(3) C1 0.0123(5) 0.0138(5) 0.0137(5) -0.0002(4) 0.0009(4) -0.0006(4) N2 0.0124(4) 0.0159(4) 0.0141(4) -0.0013(4) 0.0014(3) -0.0022(3) C2 0.0145(5) 0.0203(5) 0.0187(6) -0.0024(4) 0.0038(4) -0.0047(4) C3 0.0137(5) 0.0203(5) 0.0206(6) -0.0039(4) 0.0026(4) -0.0044(4) C4 0.0141(5) 0.0199(5) 0.0142(5) -0.0033(4) 0.0003(4) -0.0032(4) C5 0.0181(6) 0.0226(6) 0.0169(6) -0.0017(5) -0.0016(4) -0.0032(5) C6 0.0270(7) 0.0324(7) 0.0161(6) -0.0009(5) -0.0018(5) -0.0057(6) C7 0.0295(7) 0.0364(8) 0.0171(6) -0.0092(6) 0.0033(5) -0.0083(6) C8 0.0234(7) 0.0260(6) 0.0252(7) -0.0105(5) 0.0053(5) -0.0034(5) C9 0.0148(5) 0.0200(5) 0.0209(6) -0.0054(5) 0.0021(4) -0.0030(4) C10 0.0253(7) 0.0223(6) 0.0208(6) 0.0013(5) -0.0042(5) 0.0006(5) C11 0.0452(10) 0.0241(7) 0.0344(9) 0.0024(6) 0.0053(7) -0.0050(7) C12 0.0306(8) 0.0364(9) 0.0432(10) -0.0039(8) -0.0113(7) 0.0065(7) C13 0.0203(6) 0.0178(5) 0.0282(7) -0.0038(5) 0.0014(5) 0.0005(5) C14 0.0264(7) 0.0226(6) 0.0394(9) 0.0023(6) 0.0057(6) -0.0016(5) C15 0.0222(7) 0.0213(6) 0.0508(10) -0.0061(7) 0.0029(7) 0.0031(5) C16 0.0157(5) 0.0173(5) 0.0135(5) -0.0003(4) 0.0006(4) -0.0029(4) C17 0.0176(6) 0.0196(5) 0.0175(5) -0.0025(4) 0.0016(4) -0.0018(4) C18 0.0270(7) 0.0267(7) 0.0193(6) -0.0067(5) 0.0002(5) -0.0015(5) C19 0.0303(8) 0.0323(7) 0.0186(6) -0.0042(5) -0.0052(6) -0.0041(6) C20 0.0234(7) 0.0296(7) 0.0188(6) 0.0022(5) -0.0047(5) -0.0017(5) C21 0.0171(5) 0.0212(6) 0.0167(6) 0.0030(4) 0.0007(4) -0.0019(4) C22 0.0186(6) 0.0252(6) 0.0224(6) -0.0068(5) 0.0009(5) 0.0027(5) C23 0.0197(7) 0.0395(9) 0.0341(8) -0.0102(7) 0.0048(6) -0.0019(6) C24 0.0302(8) 0.0263(7) 0.0330(8) -0.0055(6) 0.0028(6) 0.0071(6) C25 0.0220(6) 0.0243(6) 0.0181(6) 0.0044(5) 0.0020(5) 0.0054(5) C26 0.0234(8) 0.0550(11) 0.0392(10) -0.0023(8) -0.0004(7) 0.0128(8) C27 0.0424(10) 0.0211(7) 0.0579(12) 0.0052(7) 0.0155(9) 0.0059(7) Cl3A 0.0504(6) 0.0609(9) 0.0350(3) 0.0049(4) 0.0081(3) 0.0119(6) Cl4A 0.0443(6) 0.0393(2) 0.0251(4) 0.0060(3) -0.0028(4) -0.0135(3) C28A 0.0290(16) 0.0500(16) 0.0185(8) 0.0000(9) -0.0016(11) -0.0023(9) Cl3B 0.0504(6) 0.0609(9) 0.0350(3) 0.0049(4) 0.0081(3) 0.0119(6) Cl4B 0.0443(6) 0.0393(2) 0.0251(4) 0.0060(3) -0.0028(4) -0.0135(3) C28B 0.0290(16) 0.0500(16) 0.0185(8) 0.0000(9) -0.0016(11) -0.0023(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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 Cl2 91.05(4) . . ? C1 Pd1 Cl1 90.82(4) . . ? Cl2 Pd1 Cl1 177.709(12) . . ? C1 Pd1 Cl1 177.82(4) . 5_666 ? Cl2 Pd1 Cl1 91.105(11) . 5_666 ? Cl1 Pd1 Cl1 87.022(11) . 5_666 ? Pd1 Cl1 Pd1 92.977(11) . 5_666 ? C1 N1 C3 110.46(10) . . ? C1 N1 C4 128.91(11) . . ? C3 N1 C4 120.49(10) . . ? N2 C1 N1 105.25(10) . . ? N2 C1 Pd1 127.04(9) . . ? N1 C1 Pd1 127.59(9) . . ? C1 N2 C2 110.34(10) . . ? C1 N2 C16 127.29(10) . . ? C2 N2 C16 122.17(10) . . ? C3 C2 N2 107.09(11) . . ? C3 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? C2 C3 N1 106.86(11) . . ? C2 C3 H3 126.6 . . ? N1 C3 H3 126.6 . . ? C5 C4 C9 123.48(12) . . ? C5 C4 N1 119.04(11) . . ? C9 C4 N1 117.18(12) . . ? C4 C5 C6 117.10(13) . . ? C4 C5 C10 123.06(12) . . ? C6 C5 C10 119.84(13) . . ? C7 C6 C5 120.95(14) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 120.52(13) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C9 121.28(14) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C4 116.62(13) . . ? C8 C9 C13 120.45(13) . . ? C4 C9 C13 122.92(12) . . ? C5 C10 C12 110.79(13) . . ? C5 C10 C11 110.69(13) . . ? C12 C10 C11 111.61(14) . . ? C5 C10 H10 107.9 . . ? C12 C10 H10 107.9 . . ? C11 C10 H10 107.9 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 111.54(12) . . ? C9 C13 C15 111.83(13) . . ? C14 C13 C15 109.34(12) . . ? C9 C13 H13 108.0 . . ? C14 C13 H13 108.0 . . ? C15 C13 H13 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 123.31(12) . . ? C17 C16 N2 118.61(11) . . ? C21 C16 N2 117.94(11) . . ? C18 C17 C16 116.87(13) . . ? C18 C17 C22 119.50(12) . . ? C16 C17 C22 123.58(12) . . ? C19 C18 C17 121.39(14) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 120.61(13) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C21 120.87(14) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C20 C21 C16 116.95(13) . . ? C20 C21 C25 120.92(13) . . ? C16 C21 C25 122.03(12) . . ? C17 C22 C24 112.71(12) . . ? C17 C22 C23 110.40(13) . . ? C24 C22 C23 109.18(13) . . ? C17 C22 H22 108.1 . . ? C24 C22 H22 108.1 . . ? C23 C22 H22 108.1 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 C26 113.54(13) . . ? C21 C25 C27 110.48(12) . . ? C26 C25 C27 110.72(14) . . ? C21 C25 H25 107.3 . . ? C26 C25 H25 107.3 . . ? C27 C25 H25 107.3 . . ? 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 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Cl4A C28A Cl3A 110.80(14) . . ? Cl4A C28A H28A 109.5 . . ? Cl3A C28A H28A 109.5 . . ? Cl4A C28A H28B 109.5 . . ? Cl3A C28A H28B 109.5 . . ? H28A C28A H28B 108.1 . . ? Cl4B C28B Cl3B 110.6(6) . . ? Cl4B C28B H28C 109.5 . . ? Cl3B C28B H28C 109.5 . . ? Cl4B C28B H28D 109.5 . . ? Cl3B C28B H28D 109.5 . . ? H28C C28B H28D 108.1 . . ? 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 1.9512(12) . ? Pd1 Cl2 2.2737(3) . ? Pd1 Cl1 2.3153(3) . ? Pd1 Cl1 2.3976(3) 5_666 ? N1 C1 1.3565(16) . ? N1 C3 1.3894(16) . ? N1 C4 1.4451(16) . ? C1 N2 1.3543(16) . ? N2 C2 1.3904(16) . ? N2 C16 1.4460(16) . ? C2 C3 1.3427(18) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C5 1.3964(19) . ? C4 C9 1.4070(18) . ? C5 C6 1.3990(19) . ? C5 C10 1.522(2) . ? C6 C7 1.382(2) . ? C6 H6 0.9500 . ? C7 C8 1.384(2) . ? C7 H7 0.9500 . ? C8 C9 1.3965(19) . ? C8 H8 0.9500 . ? C9 C13 1.517(2) . ? C10 C12 1.531(2) . ? C10 C11 1.533(2) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.534(2) . ? C13 C15 1.535(2) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.4027(18) . ? C16 C21 1.4054(18) . ? C17 C18 1.3950(19) . ? C17 C22 1.520(2) . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 C20 1.386(2) . ? C19 H19 0.9500 . ? C20 C21 1.399(2) . ? C20 H20 0.9500 . ? C21 C25 1.517(2) . ? C22 C24 1.534(2) . ? C22 C23 1.536(2) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.526(2) . ? C25 C27 1.532(2) . ? C25 H25 1.0000 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? Cl3A C28A 1.773(2) . ? Cl4A C28A 1.7586(19) . ? C28A H28A 0.9900 . ? C28A H28B 0.9900 . ? Cl3B C28B 1.773(4) . ? Cl4B C28B 1.758(3) . ? C28B H28C 0.9900 . ? C28B H28D 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 N2 -0.70(14) . . . . ? C4 N1 C1 N2 174.96(12) . . . . ? C3 N1 C1 Pd1 175.58(9) . . . . ? C4 N1 C1 Pd1 -8.76(19) . . . . ? N1 C1 N2 C2 0.29(14) . . . . ? Pd1 C1 N2 C2 -176.02(9) . . . . ? N1 C1 N2 C16 -174.58(11) . . . . ? Pd1 C1 N2 C16 9.11(18) . . . . ? C1 N2 C2 C3 0.23(15) . . . . ? C16 N2 C2 C3 175.41(12) . . . . ? N2 C2 C3 N1 -0.65(15) . . . . ? C1 N1 C3 C2 0.86(15) . . . . ? C4 N1 C3 C2 -175.22(12) . . . . ? C1 N1 C4 C5 82.41(17) . . . . ? C3 N1 C4 C5 -102.31(15) . . . . ? C1 N1 C4 C9 -103.59(15) . . . . ? C3 N1 C4 C9 71.68(16) . . . . ? C9 C4 C5 C6 -2.3(2) . . . . ? N1 C4 C5 C6 171.27(12) . . . . ? C9 C4 C5 C10 178.57(13) . . . . ? N1 C4 C5 C10 -7.83(19) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C10 C5 C6 C7 179.75(14) . . . . ? C5 C6 C7 C8 1.3(2) . . . . ? C6 C7 C8 C9 -1.5(2) . . . . ? C7 C8 C9 C4 -0.1(2) . . . . ? C7 C8 C9 C13 -179.34(14) . . . . ? C5 C4 C9 C8 2.05(19) . . . . ? N1 C4 C9 C8 -171.66(12) . . . . ? C5 C4 C9 C13 -178.70(13) . . . . ? N1 C4 C9 C13 7.60(18) . . . . ? C4 C5 C10 C12 113.33(16) . . . . ? C6 C5 C10 C12 -65.76(18) . . . . ? C4 C5 C10 C11 -122.31(15) . . . . ? C6 C5 C10 C11 58.60(18) . . . . ? C8 C9 C13 C14 76.56(17) . . . . ? C4 C9 C13 C14 -102.67(15) . . . . ? C8 C9 C13 C15 -46.24(18) . . . . ? C4 C9 C13 C15 134.54(14) . . . . ? C1 N2 C16 C17 -115.18(14) . . . . ? C2 N2 C16 C17 70.51(16) . . . . ? C1 N2 C16 C21 69.04(17) . . . . ? C2 N2 C16 C21 -105.27(14) . . . . ? C21 C16 C17 C18 -0.1(2) . . . . ? N2 C16 C17 C18 -175.69(12) . . . . ? C21 C16 C17 C22 177.09(13) . . . . ? N2 C16 C17 C22 1.55(19) . . . . ? C16 C17 C18 C19 -0.6(2) . . . . ? C22 C17 C18 C19 -177.92(14) . . . . ? C17 C18 C19 C20 0.7(2) . . . . ? C18 C19 C20 C21 -0.2(2) . . . . ? C19 C20 C21 C16 -0.5(2) . . . . ? C19 C20 C21 C25 175.88(14) . . . . ? C17 C16 C21 C20 0.7(2) . . . . ? N2 C16 C21 C20 176.24(12) . . . . ? C17 C16 C21 C25 -175.67(12) . . . . ? N2 C16 C21 C25 -0.10(18) . . . . ? C18 C17 C22 C24 -50.32(18) . . . . ? C16 C17 C22 C24 132.51(14) . . . . ? C18 C17 C22 C23 72.07(17) . . . . ? C16 C17 C22 C23 -105.10(15) . . . . ? C20 C21 C25 C26 32.02(19) . . . . ? C16 C21 C25 C26 -151.78(14) . . . . ? C20 C21 C25 C27 -93.04(17) . . . . ? C16 C21 C25 C27 83.15(17) . . . . ?