#------------------------------------------------------------------------------ #$Date: 2021-11-04 03:30:35 +0200 (Thu, 04 Nov 2021) $ #$Revision: 270286 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061036.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_7061036 loop_ _publ_author_name 'Hamdi, N.' 'Slimani, I.' 'Mansour, L.' 'Alresheedi, Faisal' 'G\"urb\"uz, N.' '\"Ozdemir, I.' _publ_section_title ; N-Heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C--H bond activation of heteroarene derivatives with aryl bromides: synthesis, and antimicrobial and antioxidant activities ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04606C _journal_year 2021 _chemical_formula_moiety 'C27 H27 Cl2 N3 Pd' _chemical_formula_sum 'C27 H27 Cl2 N3 Pd' _chemical_formula_weight 570.81 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/ccdc.csd.cc27zbzk _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-19 deposited with the CCDC. 2021-11-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.781(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.2530(4) _cell_length_b 12.4840(6) _cell_length_c 21.9892(9) _cell_measurement_reflns_used 12953 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.09 _cell_measurement_theta_min 1.85 _cell_volume 2534.54(19) _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-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SIR-2019 (Burla et al., 2015)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _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 0.0416 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 14031 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.661 _diffrn_reflns_theta_min 1.877 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_T_max 0.8883 _exptl_absorpt_correction_T_min 0.6503 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.496 _exptl_crystal_description prism _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.760 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.469 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.882 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 311 _refine_ls_number_reflns 5878 _refine_ls_number_restraints 44 _refine_ls_restrained_S_all 0.896 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0367 _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^)+(0.0411P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.0826 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3772 _reflns_number_total 5878 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04606c2.cif _cod_data_source_block namiko140 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7061036 _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 0.528 _shelx_estimated_absorpt_t_max 0.869 _shelx_res_file ; TITL namiko140 shelx.res created by SHELXL-2018/3 at 20:35:44 on 19-May-2021 CELL 0.71073 9.2530 12.4840 21.9892 90.000 93.781 90.000 ZERR 4.00 0.0004 0.0006 0.0009 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H CL N PD UNIT 108 108 8 12 4 MERG 2 SADI 0.004 C8 C10A C8 C10B SADI 0.004 C9 C10A C9 C10B SADI 0.004 C11 C10A C11 C10B SIMU 0.004 C8 C9 C10A C10B C11 DELU 0.004 C8 C9 C10A C10B C11 DFIX 1.460 0.002 C9 C10A DFIX 1.460 0.002 C9 C10B FMAP 2 PLAN 5 SIZE 0.150 0.190 0.760 ACTA BOND $H CONF L.S. 20 TEMP 23.00 WGHT 0.041100 FVAR 0.37966 0.53661 PD1 5 0.184516 0.437352 0.683597 11.00000 0.04866 0.05033 = 0.05637 -0.00023 0.01654 -0.00533 CL1 3 0.069701 0.360116 0.598668 11.00000 0.05761 0.07872 = 0.06550 -0.00542 0.01300 -0.01871 CL2 3 0.296245 0.516370 0.768573 11.00000 0.08835 0.08125 = 0.06287 -0.01188 0.01757 -0.02222 N1 4 0.327620 0.570246 0.591927 11.00000 0.04353 0.04709 = 0.05256 -0.00001 0.00810 -0.00341 N2 4 0.477318 0.459325 0.639193 11.00000 0.04484 0.05196 = 0.05492 0.00264 0.00942 -0.00341 N3 4 0.028195 0.371538 0.737028 11.00000 0.05163 0.06509 = 0.05687 0.00257 0.01452 -0.00425 C1 1 0.337559 0.492574 0.634294 11.00000 0.04696 0.04635 = 0.05061 -0.00696 0.00881 -0.00466 C2 1 0.462520 0.586864 0.568256 11.00000 0.04486 0.04735 = 0.05063 -0.00501 0.00933 -0.00599 C3 1 0.507134 0.655029 0.523173 11.00000 0.06027 0.05203 = 0.05445 -0.00176 0.00995 -0.00607 AFIX 43 H3 2 0.443501 0.702089 0.502406 11.00000 -1.20000 AFIX 0 C4 1 0.652114 0.648821 0.510933 11.00000 0.06359 0.06382 = 0.05877 -0.00258 0.01895 -0.01757 AFIX 43 H4 2 0.686380 0.692731 0.480895 11.00000 -1.20000 AFIX 0 C5 1 0.746651 0.579871 0.541775 11.00000 0.04603 0.07367 = 0.06934 -0.00742 0.01717 -0.01491 AFIX 43 H5 2 0.843152 0.579207 0.532336 11.00000 -1.20000 AFIX 0 C6 1 0.702899 0.511801 0.586185 11.00000 0.04474 0.06642 = 0.06257 -0.00850 0.00780 -0.00373 AFIX 43 H6 2 0.767196 0.465197 0.606938 11.00000 -1.20000 AFIX 0 C7 1 0.556959 0.516331 0.598475 11.00000 0.04805 0.05082 = 0.04886 -0.00754 0.00908 -0.00745 C8 1 0.195177 0.627142 0.572200 11.00000 0.05533 0.05034 = 0.09978 0.00437 0.02217 0.00211 AFIX 23 H8A 2 0.113404 0.579819 0.576656 11.00000 -1.20000 H8B 2 0.198023 0.643997 0.529234 11.00000 -1.20000 AFIX 0 C9 1 0.170451 0.729122 0.606489 11.00000 0.08331 0.06208 = 0.12972 -0.00782 0.03941 0.00056 PART 1 AFIX 13 H9A 2 0.086602 0.756690 0.581762 21.00000 -1.20000 AFIX 13 PART 2 H9B 2 0.201268 0.706515 0.648014 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C10A 1 0.105374 0.718765 0.664573 21.00000 0.10134 0.07581 = 0.12461 -0.01454 0.04204 0.00591 AFIX 137 H10A 2 0.177468 0.695605 0.695153 21.00000 -1.50000 H10B 2 0.028502 0.667056 0.660890 21.00000 -1.50000 H10C 2 0.067163 0.786791 0.676044 21.00000 -1.50000 PART 2 AFIX 0 C10B 1 0.020025 0.757340 0.614485 -21.00000 0.08017 0.07699 = 0.14932 -0.01781 0.02936 0.01411 AFIX 137 H10D 2 0.016661 0.814895 0.643310 -21.00000 -1.50000 H10E 2 -0.029870 0.696218 0.629316 -21.00000 -1.50000 H10F 2 -0.025786 0.779491 0.576094 -21.00000 -1.50000 PART 0 AFIX 0 C11 1 0.271328 0.816698 0.598540 11.00000 0.09826 0.06590 = 0.13482 -0.01763 0.03380 -0.01125 AFIX 137 H11A 2 0.243702 0.877422 0.621917 11.00000 -1.50000 H11B 2 0.269457 0.835910 0.556222 11.00000 -1.50000 H11C 2 0.367357 0.794523 0.612238 11.00000 -1.50000 AFIX 0 C12 1 0.536712 0.375111 0.679100 11.00000 0.05625 0.06779 = 0.05224 0.00547 -0.00015 0.00215 AFIX 23 H12A 2 0.471110 0.362737 0.711011 11.00000 -1.20000 H12B 2 0.628212 0.399382 0.698372 11.00000 -1.20000 AFIX 0 C13 1 0.560925 0.271296 0.647089 11.00000 0.05449 0.05651 = 0.05296 0.00735 0.00344 -0.00253 C14 1 0.696892 0.238641 0.634942 11.00000 0.05672 0.05743 = 0.06578 0.00461 -0.00062 -0.00631 AFIX 43 H14 2 0.775238 0.282298 0.646721 11.00000 -1.20000 AFIX 0 C15 1 0.722797 0.141189 0.605205 11.00000 0.06175 0.05369 = 0.06432 0.00429 0.00370 -0.00446 C16 1 0.863610 0.106206 0.593421 11.00000 0.07193 0.07038 = 0.10154 -0.00771 0.02483 -0.00226 AFIX 43 H16 2 0.942965 0.148850 0.605235 11.00000 -1.20000 AFIX 0 C17 1 0.884741 0.011594 0.565206 11.00000 0.09372 0.08266 = 0.10414 -0.00805 0.03187 0.00719 AFIX 43 H17 2 0.978119 -0.010152 0.557843 11.00000 -1.20000 AFIX 0 C18 1 0.768033 -0.052758 0.547313 11.00000 0.11404 0.07434 = 0.08132 -0.01739 0.01131 0.00700 AFIX 43 H18 2 0.783810 -0.117482 0.527887 11.00000 -1.20000 AFIX 0 C19 1 0.631414 -0.023071 0.557613 11.00000 0.09937 0.06192 = 0.07887 0.00022 -0.00883 -0.00831 AFIX 43 H19 2 0.554355 -0.067429 0.545099 11.00000 -1.20000 AFIX 0 C20 1 0.604120 0.075504 0.587454 11.00000 0.07323 0.05594 = 0.05877 0.00560 -0.00189 -0.00466 C21 1 0.464277 0.109256 0.601351 11.00000 0.06411 0.06209 = 0.09151 0.00983 -0.01161 -0.01721 AFIX 43 H21 2 0.384925 0.065959 0.590522 11.00000 -1.20000 AFIX 0 C22 1 0.443597 0.203031 0.630012 11.00000 0.05179 0.06372 = 0.08251 0.01210 0.00475 -0.00237 AFIX 43 H22 2 0.350348 0.223054 0.638673 11.00000 -1.20000 AFIX 0 C23 1 0.023299 0.265418 0.742978 11.00000 0.06377 0.06106 = 0.07387 0.01074 0.01298 -0.00355 AFIX 43 H23 2 0.088292 0.223586 0.722873 11.00000 -1.20000 AFIX 0 C24 1 -0.074434 0.216038 0.777769 11.00000 0.08128 0.08649 = 0.08359 0.03175 0.00809 -0.01511 AFIX 43 H24 2 -0.074628 0.141868 0.781711 11.00000 -1.20000 AFIX 0 C25 1 -0.171327 0.276766 0.806526 11.00000 0.06759 0.13553 = 0.06425 0.01177 0.01675 -0.03190 AFIX 43 H25 2 -0.238472 0.244551 0.830341 11.00000 -1.20000 AFIX 0 C26 1 -0.168835 0.384802 0.800054 11.00000 0.05801 0.12344 = 0.06240 -0.01489 0.01692 -0.00766 AFIX 43 H26 2 -0.235480 0.427596 0.818586 11.00000 -1.20000 AFIX 0 C27 1 -0.065582 0.430124 0.765456 11.00000 0.05883 0.08369 = 0.06559 -0.01018 0.01435 -0.00479 AFIX 43 H27 2 -0.061856 0.504308 0.762029 11.00000 -1.20000 AFIX 0 HKLF 4 REM namiko140 REM wR2 = 0.0826, GooF = S = 0.882, Restrained GooF = 0.896 for all data REM R1 = 0.0367 for 3772 Fo > 4sig(Fo) and 0.0721 for all 5878 data REM 311 parameters refined using 44 restraints END WGHT 0.0411 0.0000 REM Highest difference peak 0.469, deepest hole -0.384, 1-sigma level 0.063 Q1 1 0.2660 0.4398 0.6473 11.00000 0.05 0.47 Q2 1 0.0254 0.7631 0.5638 11.00000 0.05 0.43 Q3 1 0.1524 0.3575 0.6677 11.00000 0.05 0.40 Q4 1 0.0884 0.4195 0.7177 11.00000 0.05 0.37 Q5 1 0.1513 0.5280 0.6742 11.00000 0.05 0.36 ; _shelx_res_checksum 54273 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.18452(3) 0.43735(2) 0.68360(2) 0.05121(9) Uani 1 1 d . . . . . Cl1 Cl 0.06970(9) 0.36012(8) 0.59867(4) 0.0669(2) Uani 1 1 d . . . . . Cl2 Cl 0.29624(11) 0.51637(8) 0.76857(4) 0.0769(3) Uani 1 1 d . . . . . N1 N 0.3276(2) 0.5702(2) 0.59193(11) 0.0475(6) Uani 1 1 d . . . . . N2 N 0.4773(3) 0.4593(2) 0.63919(12) 0.0503(6) Uani 1 1 d . . . . . N3 N 0.0282(3) 0.3715(2) 0.73703(13) 0.0574(7) Uani 1 1 d . . . . . C1 C 0.3376(3) 0.4926(2) 0.63429(14) 0.0477(7) Uani 1 1 d . . . . . C2 C 0.4625(3) 0.5869(2) 0.56826(15) 0.0473(7) Uani 1 1 d . . . . . C3 C 0.5071(3) 0.6550(3) 0.52317(15) 0.0553(8) Uani 1 1 d . . . . . H3 H 0.443501 0.702089 0.502406 0.066 Uiso 1 1 calc R U . . . C4 C 0.6521(4) 0.6488(3) 0.51093(16) 0.0614(9) Uani 1 1 d . . . . . H4 H 0.686380 0.692731 0.480895 0.074 Uiso 1 1 calc R U . . . C5 C 0.7467(3) 0.5799(3) 0.54177(17) 0.0624(9) Uani 1 1 d . . . . . H5 H 0.843152 0.579207 0.532336 0.075 Uiso 1 1 calc R U . . . C6 C 0.7029(3) 0.5118(3) 0.58619(16) 0.0577(8) Uani 1 1 d . . . . . H6 H 0.767196 0.465197 0.606938 0.069 Uiso 1 1 calc R U . . . C7 C 0.5570(3) 0.5163(2) 0.59847(14) 0.0490(7) Uani 1 1 d . . . . . C8 C 0.1952(3) 0.6271(3) 0.57220(19) 0.0677(9) Uani 1 1 d D U . . . H8A H 0.113404 0.579819 0.576656 0.081 Uiso 1 1 calc R U . . . H8B H 0.198023 0.643997 0.529234 0.081 Uiso 1 1 calc R U . . . C9 C 0.1705(4) 0.7291(3) 0.60649(19) 0.0903(11) Uani 1 1 d D U . . . H9A H 0.086602 0.756690 0.581762 0.108 Uiso 0.537(7) 1 calc R U P A 1 H9B H 0.201268 0.706515 0.648014 0.108 Uiso 0.463(7) 1 calc R U P A 2 C10A C 0.1054(10) 0.7188(6) 0.6646(3) 0.099(2) Uani 0.537(7) 1 d D U P A 1 H10A H 0.177468 0.695605 0.695153 0.149 Uiso 0.537(7) 1 calc R U P A 1 H10B H 0.028502 0.667056 0.660890 0.149 Uiso 0.537(7) 1 calc R U P A 1 H10C H 0.067163 0.786791 0.676044 0.149 Uiso 0.537(7) 1 calc R U P A 1 C10B C 0.0200(5) 0.7573(6) 0.6145(6) 0.101(2) Uani 0.463(7) 1 d D U P A 2 H10D H 0.016661 0.814895 0.643310 0.152 Uiso 0.463(7) 1 calc R U P A 2 H10E H -0.029870 0.696218 0.629316 0.152 Uiso 0.463(7) 1 calc R U P A 2 H10F H -0.025786 0.779491 0.576094 0.152 Uiso 0.463(7) 1 calc R U P A 2 C11 C 0.2713(5) 0.8167(3) 0.5985(2) 0.0985(14) Uani 1 1 d D U . . . H11A H 0.243702 0.877422 0.621917 0.148 Uiso 1 1 calc R U . . . H11B H 0.269457 0.835910 0.556222 0.148 Uiso 1 1 calc R U . . . H11C H 0.367357 0.794523 0.612238 0.148 Uiso 1 1 calc R U . . . C12 C 0.5367(4) 0.3751(3) 0.67910(16) 0.0589(8) Uani 1 1 d . . . . . H12A H 0.471110 0.362737 0.711011 0.071 Uiso 1 1 calc R U . . . H12B H 0.628212 0.399382 0.698372 0.071 Uiso 1 1 calc R U . . . C13 C 0.5609(3) 0.2713(3) 0.64709(15) 0.0547(8) Uani 1 1 d . . . . . C14 C 0.6969(4) 0.2386(3) 0.63494(16) 0.0602(8) Uani 1 1 d . . . . . H14 H 0.775238 0.282298 0.646721 0.072 Uiso 1 1 calc R U . . . C15 C 0.7228(4) 0.1412(3) 0.60520(17) 0.0599(9) Uani 1 1 d . . . . . C16 C 0.8636(4) 0.1062(3) 0.5934(2) 0.0804(12) Uani 1 1 d . . . . . H16 H 0.942965 0.148850 0.605235 0.097 Uiso 1 1 calc R U . . . C17 C 0.8847(5) 0.0116(4) 0.5652(2) 0.0924(14) Uani 1 1 d . . . . . H17 H 0.978119 -0.010152 0.557843 0.111 Uiso 1 1 calc R U . . . C18 C 0.7680(6) -0.0528(4) 0.5473(2) 0.0897(13) Uani 1 1 d . . . . . H18 H 0.783810 -0.117482 0.527887 0.108 Uiso 1 1 calc R U . . . C19 C 0.6314(5) -0.0231(3) 0.5576(2) 0.0807(11) Uani 1 1 d . . . . . H19 H 0.554355 -0.067429 0.545099 0.097 Uiso 1 1 calc R U . . . C20 C 0.6041(4) 0.0755(3) 0.58745(17) 0.0629(9) Uani 1 1 d . . . . . C21 C 0.4643(4) 0.1093(3) 0.6014(2) 0.0733(11) Uani 1 1 d . . . . . H21 H 0.384925 0.065959 0.590522 0.088 Uiso 1 1 calc R U . . . C22 C 0.4436(4) 0.2030(3) 0.63001(18) 0.0660(10) Uani 1 1 d . . . . . H22 H 0.350348 0.223054 0.638673 0.079 Uiso 1 1 calc R U . . . C23 C 0.0233(4) 0.2654(3) 0.74298(18) 0.0659(9) Uani 1 1 d . . . . . H23 H 0.088292 0.223586 0.722873 0.079 Uiso 1 1 calc R U . . . C24 C -0.0744(5) 0.2160(4) 0.7778(2) 0.0837(12) Uani 1 1 d . . . . . H24 H -0.074628 0.141868 0.781711 0.100 Uiso 1 1 calc R U . . . C25 C -0.1713(4) 0.2768(5) 0.80653(19) 0.0886(14) Uani 1 1 d . . . . . H25 H -0.238472 0.244551 0.830341 0.106 Uiso 1 1 calc R U . . . C26 C -0.1688(4) 0.3848(4) 0.80005(19) 0.0807(12) Uani 1 1 d . . . . . H26 H -0.235480 0.427596 0.818586 0.097 Uiso 1 1 calc R U . . . C27 C -0.0656(4) 0.4301(3) 0.76546(17) 0.0689(10) Uani 1 1 d . . . . . H27 H -0.061856 0.504308 0.762029 0.083 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 0.04866(13) 0.05033(13) 0.05637(15) -0.00023(13) 0.01654(10) -0.00533(12) Cl1 0.0576(4) 0.0787(6) 0.0655(6) -0.0054(5) 0.0130(4) -0.0187(4) Cl2 0.0883(6) 0.0812(6) 0.0629(6) -0.0119(5) 0.0176(5) -0.0222(5) N1 0.0435(12) 0.0471(14) 0.0526(14) 0.0000(12) 0.0081(11) -0.0034(11) N2 0.0448(13) 0.0520(15) 0.0549(16) 0.0026(12) 0.0094(12) -0.0034(11) N3 0.0516(14) 0.0651(18) 0.0569(17) 0.0026(14) 0.0145(13) -0.0042(13) C1 0.0470(16) 0.0464(17) 0.0506(18) -0.0070(14) 0.0088(14) -0.0047(13) C2 0.0449(15) 0.0474(17) 0.0506(17) -0.0050(14) 0.0093(14) -0.0060(13) C3 0.0603(18) 0.0520(18) 0.054(2) -0.0018(16) 0.0099(16) -0.0061(15) C4 0.064(2) 0.064(2) 0.059(2) -0.0026(18) 0.0190(18) -0.0176(18) C5 0.0460(16) 0.074(2) 0.069(2) -0.0074(19) 0.0172(17) -0.0149(17) C6 0.0447(16) 0.066(2) 0.063(2) -0.0085(18) 0.0078(16) -0.0037(15) C7 0.0481(16) 0.0508(16) 0.0489(18) -0.0075(15) 0.0091(14) -0.0074(14) C8 0.0553(17) 0.0503(16) 0.100(3) 0.0044(17) 0.0222(18) 0.0021(14) C9 0.083(2) 0.0621(18) 0.130(3) -0.008(2) 0.039(2) 0.0006(16) C10A 0.101(4) 0.076(4) 0.125(5) -0.015(3) 0.042(4) 0.006(4) C10B 0.080(3) 0.077(4) 0.149(6) -0.018(4) 0.029(4) 0.014(3) C11 0.098(3) 0.066(2) 0.135(4) -0.018(2) 0.034(3) -0.011(2) C12 0.0563(18) 0.068(2) 0.052(2) 0.0055(17) -0.0001(16) 0.0021(16) C13 0.0545(17) 0.0565(19) 0.0530(19) 0.0074(16) 0.0034(15) -0.0025(15) C14 0.0567(18) 0.057(2) 0.066(2) 0.0046(17) -0.0006(17) -0.0063(16) C15 0.0618(19) 0.0537(19) 0.064(2) 0.0043(17) 0.0037(17) -0.0045(16) C16 0.072(2) 0.070(2) 0.102(3) -0.008(2) 0.025(2) -0.0023(19) C17 0.094(3) 0.083(3) 0.104(4) -0.008(3) 0.032(3) 0.007(3) C18 0.114(4) 0.074(3) 0.081(3) -0.017(2) 0.011(3) 0.007(3) C19 0.099(3) 0.062(2) 0.079(3) 0.000(2) -0.009(2) -0.008(2) C20 0.073(2) 0.056(2) 0.059(2) 0.0056(18) -0.0019(18) -0.0047(18) C21 0.064(2) 0.062(2) 0.092(3) 0.010(2) -0.012(2) -0.0172(18) C22 0.0518(18) 0.064(2) 0.083(3) 0.012(2) 0.0047(18) -0.0024(16) C23 0.064(2) 0.061(2) 0.074(2) 0.0107(19) 0.0130(19) -0.0036(17) C24 0.081(3) 0.086(3) 0.084(3) 0.032(2) 0.008(2) -0.015(2) C25 0.068(2) 0.136(4) 0.064(3) 0.012(3) 0.017(2) -0.032(3) C26 0.058(2) 0.123(4) 0.062(2) -0.015(2) 0.0169(19) -0.008(2) C27 0.0588(19) 0.084(3) 0.066(2) -0.010(2) 0.0143(17) -0.0048(19) 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' Cl Cl 0.1484 0.1585 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D1NJ04606C 2021 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 N3 177.04(12) . . ? C1 Pd1 Cl2 89.78(10) . . ? N3 Pd1 Cl2 90.15(8) . . ? C1 Pd1 Cl1 90.58(9) . . ? N3 Pd1 Cl1 89.54(8) . . ? Cl2 Pd1 Cl1 179.10(4) . . ? C1 N1 C2 110.1(2) . . ? C1 N1 C8 125.2(2) . . ? C2 N1 C8 124.8(3) . . ? C1 N2 C7 109.6(3) . . ? C1 N2 C12 126.2(2) . . ? C7 N2 C12 124.2(2) . . ? C27 N3 C23 118.4(3) . . ? C27 N3 Pd1 123.2(2) . . ? C23 N3 Pd1 118.4(2) . . ? N1 C1 N2 107.3(2) . . ? N1 C1 Pd1 128.1(2) . . ? N2 C1 Pd1 124.6(2) . . ? C7 C2 C3 121.7(3) . . ? C7 C2 N1 106.2(2) . . ? C3 C2 N1 132.1(3) . . ? C4 C3 C2 116.1(3) . . ? C4 C3 H3 121.9 . . ? C2 C3 H3 121.9 . . ? C5 C4 C3 122.1(3) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 122.0(3) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C7 116.5(3) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? C2 C7 N2 106.9(2) . . ? C2 C7 C6 121.5(3) . . ? N2 C7 C6 131.6(3) . . ? N1 C8 C9 114.6(3) . . ? N1 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? N1 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10A C9 C11 118.6(4) . . ? C11 C9 C10B 117.3(4) . . ? C10A C9 C8 116.8(4) . . ? C11 C9 C8 117.1(3) . . ? C10B C9 C8 116.3(4) . . ? C10A C9 H9A 99.2 . . ? C11 C9 H9A 99.2 . . ? C8 C9 H9A 99.2 . . ? C11 C9 H9B 100.3 . . ? C10B C9 H9B 100.3 . . ? C8 C9 H9B 100.3 . . ? C9 C10A H10A 109.5 . . ? C9 C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9 C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C9 C10B H10D 109.5 . . ? C9 C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9 C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 113.8(3) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C22 118.0(3) . . ? C14 C13 C12 121.2(3) . . ? C22 C13 C12 120.7(3) . . ? C13 C14 C15 122.4(3) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C20 C15 C14 118.6(3) . . ? C20 C15 C16 118.8(3) . . ? C14 C15 C16 122.6(3) . . ? C17 C16 C15 121.1(4) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 121.0(4) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C15 C20 C21 118.4(3) . . ? C15 C20 C19 118.2(4) . . ? C21 C20 C19 123.3(4) . . ? C22 C21 C20 121.3(3) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C21 C22 C13 121.2(3) . . ? C21 C22 H22 119.4 . . ? C13 C22 H22 119.4 . . ? N3 C23 C24 122.0(4) . . ? N3 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 119.2(4) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C26 C25 C24 119.3(3) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C27 118.8(4) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? N3 C27 C26 122.2(4) . . ? N3 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? 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 1.964(3) . ? Pd1 N3 2.091(2) . ? Pd1 Cl2 2.2975(11) . ? Pd1 Cl1 2.2988(10) . ? N1 C1 1.344(4) . ? N1 C2 1.399(3) . ? N1 C8 1.458(4) . ? N2 C1 1.356(4) . ? N2 C7 1.392(4) . ? N2 C12 1.454(4) . ? N3 C27 1.323(4) . ? N3 C23 1.332(4) . ? C2 C7 1.380(5) . ? C2 C3 1.390(4) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(5) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.396(4) . ? C6 H6 0.9300 . ? C8 C9 1.505(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10A 1.4533(18) . ? C9 C11 1.456(5) . ? C9 C10B 1.4576(18) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.499(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.366(4) . ? C13 C22 1.411(5) . ? C14 C15 1.409(5) . ? C14 H14 0.9300 . ? C15 C20 1.405(5) . ? C15 C16 1.414(5) . ? C16 C17 1.354(6) . ? C16 H16 0.9300 . ? C17 C18 1.382(7) . ? C17 H17 0.9300 . ? C18 C19 1.351(6) . ? C18 H18 0.9300 . ? C19 C20 1.425(5) . ? C19 H19 0.9300 . ? C20 C21 1.413(5) . ? C21 C22 1.349(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.369(5) . ? C23 H23 0.9300 . ? C24 C25 1.361(6) . ? C24 H24 0.9300 . ? C25 C26 1.357(7) . ? C25 H25 0.9300 . ? C26 C27 1.381(5) . ? C26 H26 0.9300 . ? C27 H27 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 0.8(3) . . . . ? C8 N1 C1 N2 179.3(3) . . . . ? C2 N1 C1 Pd1 178.8(2) . . . . ? C8 N1 C1 Pd1 -2.7(5) . . . . ? C7 N2 C1 N1 -0.8(3) . . . . ? C12 N2 C1 N1 -179.0(3) . . . . ? C7 N2 C1 Pd1 -178.8(2) . . . . ? C12 N2 C1 Pd1 2.9(4) . . . . ? C1 N1 C2 C7 -0.6(3) . . . . ? C8 N1 C2 C7 -179.1(3) . . . . ? C1 N1 C2 C3 178.1(3) . . . . ? C8 N1 C2 C3 -0.4(5) . . . . ? C7 C2 C3 C4 -0.7(5) . . . . ? N1 C2 C3 C4 -179.2(3) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C3 C2 C7 N2 -178.8(3) . . . . ? N1 C2 C7 N2 0.1(3) . . . . ? C3 C2 C7 C6 1.5(5) . . . . ? N1 C2 C7 C6 -179.6(3) . . . . ? C1 N2 C7 C2 0.4(3) . . . . ? C12 N2 C7 C2 178.7(3) . . . . ? C1 N2 C7 C6 -179.9(3) . . . . ? C12 N2 C7 C6 -1.6(5) . . . . ? C5 C6 C7 C2 -1.1(5) . . . . ? C5 C6 C7 N2 179.3(3) . . . . ? C1 N1 C8 C9 92.3(4) . . . . ? C2 N1 C8 C9 -89.4(4) . . . . ? N1 C8 C9 C10A -82.7(5) . . . . ? N1 C8 C9 C11 66.7(4) . . . . ? N1 C8 C9 C10B -147.6(5) . . . . ? C1 N2 C12 C13 102.5(3) . . . . ? C7 N2 C12 C13 -75.5(4) . . . . ? N2 C12 C13 C14 105.2(4) . . . . ? N2 C12 C13 C22 -76.5(4) . . . . ? C22 C13 C14 C15 1.3(5) . . . . ? C12 C13 C14 C15 179.7(3) . . . . ? C13 C14 C15 C20 0.0(5) . . . . ? C13 C14 C15 C16 -178.9(4) . . . . ? C20 C15 C16 C17 0.4(6) . . . . ? C14 C15 C16 C17 179.4(4) . . . . ? C15 C16 C17 C18 0.0(7) . . . . ? C16 C17 C18 C19 -0.2(8) . . . . ? C17 C18 C19 C20 -0.2(7) . . . . ? C14 C15 C20 C21 -1.2(5) . . . . ? C16 C15 C20 C21 177.8(4) . . . . ? C14 C15 C20 C19 -179.8(3) . . . . ? C16 C15 C20 C19 -0.8(5) . . . . ? C18 C19 C20 C15 0.7(6) . . . . ? C18 C19 C20 C21 -177.8(4) . . . . ? C15 C20 C21 C22 1.1(6) . . . . ? C19 C20 C21 C22 179.6(4) . . . . ? C20 C21 C22 C13 0.2(6) . . . . ? C14 C13 C22 C21 -1.4(6) . . . . ? C12 C13 C22 C21 -179.8(3) . . . . ? C27 N3 C23 C24 -0.5(6) . . . . ? Pd1 N3 C23 C24 179.1(3) . . . . ? N3 C23 C24 C25 1.0(6) . . . . ? C23 C24 C25 C26 0.0(7) . . . . ? C24 C25 C26 C27 -1.4(7) . . . . ? C23 N3 C27 C26 -1.0(6) . . . . ? Pd1 N3 C27 C26 179.4(3) . . . . ? C25 C26 C27 N3 2.0(6) . . . . ?