#------------------------------------------------------------------------------ #$Date: 2021-09-30 00:46:04 +0300 (Thu, 30 Sep 2021) $ #$Revision: 269372 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564770.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_1564770 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_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D1CY01601F _journal_year 2021 _chemical_formula_moiety 'C54 H74 I2 N4 O2 Pd2' _chemical_formula_sum 'C54 H74 I2 N4 O2 Pd2' _chemical_formula_weight 1277.77 _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 mixed _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 105.0300(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 25.3642(7) _cell_length_b 12.2415(3) _cell_length_c 18.7483(5) _cell_measurement_reflns_used 9034 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 34.37 _cell_measurement_theta_min 2.28 _cell_volume 5622.1(3) _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 120(2) _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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_unetI/netI 0.0261 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 21362 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 34.348 _diffrn_reflns_theta_min 2.250 _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 1.778 _exptl_absorpt_correction_T_max 0.1649 _exptl_absorpt_correction_T_min 0.1027 _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 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2560 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _refine_diff_density_max 1.232 _refine_diff_density_min -0.705 _refine_diff_density_rms 0.089 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 317 _refine_ls_number_reflns 21362 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0337 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0153P)^2^+9.6443P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.0661 _reflns_Friedel_coverage 0.000 _reflns_number_gt 18656 _reflns_number_total 21362 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cy01601f2.cif _cod_data_source_block 3C _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1564770 _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 0.600 _shelx_estimated_absorpt_t_max 0.789 _shelx_res_file ; TITL MM3C in C2/c MM3C.res created by SHELXL-2018/3 at 17:37:57 on 08-Apr-2021 CELL 0.71073 25.3642 12.2415 18.7483 90.000 105.030 90.000 ZERR 4.000 0.0007 0.0003 0.0005 0.000 0.001 0.000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H N O PD I UNIT 216 296 16 8 8 8 TEMP -153.15 SIZE 0.14 0.25 0.32 OMIT -4 68.7 OMIT -1 1 1 OMIT 1 1 0 OMIT -22 6 26 L.S. 10 LIST 4 FMAP 2 PLAN 20 MERG 0 ACTA BOND $H CONF SADI 0.003 C17 C22A C17 C22B SADI 0.003 C22A C23A C22B C23B SADI 0.003 C22A C24A C22B C24B EADP C22A C22B EADP C23A C23B EADP C24A C24B DFIX 0.84 0.02 O1 H1A O1 H1B WGHT 0.015300 9.644300 BASF 0.46495 FVAR 0.16908 0.59099 0.74093 I1 6 0.391352 0.666575 0.576342 11.00000 0.02721 0.04827 = 0.02177 0.00137 0.00497 0.00399 PD1 5 0.438988 0.618688 0.710596 11.00000 0.01875 0.02443 = 0.02062 -0.00199 0.00442 -0.00077 O1 4 0.512182 0.585580 0.685728 11.00000 0.02139 0.03816 = 0.02507 -0.00047 0.00568 0.00024 PART 1 31 H1A 2 0.518136 0.625292 0.654716 31.00000 -1.20000 PART 2 -31 H1B 2 0.510700 0.530826 0.660172 -31.00000 -1.20000 PART 0 N1 3 0.360471 0.721859 0.783787 11.00000 0.02018 0.02988 = 0.02552 -0.00455 0.00623 -0.00090 C1 1 0.370915 0.641046 0.739669 11.00000 0.02148 0.02744 = 0.02035 -0.00069 0.00362 -0.00185 N2 3 0.323648 0.582286 0.720546 11.00000 0.02236 0.03229 = 0.02285 -0.00308 0.00556 -0.00550 C2 1 0.284551 0.628296 0.751558 11.00000 0.02293 0.04553 = 0.03295 -0.00548 0.01077 -0.00702 AFIX 43 H2 2 0.248387 0.602474 0.745986 11.00000 -1.20000 AFIX 0 C3 1 0.307200 0.715432 0.790600 11.00000 0.02354 0.04052 = 0.03423 -0.00599 0.01231 -0.00183 AFIX 43 H3 2 0.290269 0.763553 0.817691 11.00000 -1.20000 AFIX 0 C4 1 0.399430 0.800546 0.823438 11.00000 0.02033 0.02895 = 0.02662 -0.00682 0.00513 0.00065 C5 1 0.425144 0.778948 0.897984 11.00000 0.02602 0.03447 = 0.02604 -0.00580 0.00554 0.00236 C6 1 0.461693 0.857551 0.935081 11.00000 0.03589 0.04676 = 0.02920 -0.01089 0.00251 -0.00194 AFIX 43 H6 2 0.480552 0.845875 0.985312 11.00000 -1.20000 AFIX 0 C7 1 0.471060 0.952010 0.900355 11.00000 0.04395 0.04515 = 0.04101 -0.01881 0.00768 -0.01418 AFIX 43 H7 2 0.496097 1.004582 0.927001 11.00000 -1.20000 AFIX 0 C8 1 0.444408 0.971300 0.827021 11.00000 0.04254 0.03154 = 0.04151 -0.00785 0.01270 -0.00718 AFIX 43 H8 2 0.451219 1.037105 0.804069 11.00000 -1.20000 AFIX 0 C9 1 0.407698 0.895149 0.786558 11.00000 0.02602 0.03053 = 0.03046 -0.00458 0.00832 0.00099 C10 1 0.412827 0.677649 0.938163 11.00000 0.03255 0.04003 = 0.02882 0.00120 0.00787 0.00585 AFIX 13 H10 2 0.397443 0.620548 0.900349 11.00000 -1.20000 AFIX 0 C11 1 0.463149 0.630051 0.992381 11.00000 0.04102 0.07200 = 0.04792 0.02295 0.01687 0.01680 AFIX 137 H11A 2 0.453431 0.561141 1.012351 11.00000 -1.50000 H11B 2 0.476687 0.681836 1.032853 11.00000 -1.50000 H11C 2 0.491645 0.616609 0.966754 11.00000 -1.50000 AFIX 0 C12 1 0.370079 0.702974 0.980562 11.00000 0.04498 0.06641 = 0.05203 0.01165 0.02717 0.01496 AFIX 137 H12A 2 0.362490 0.636739 1.005533 11.00000 -1.50000 H12B 2 0.336389 0.728381 0.945951 11.00000 -1.50000 H12C 2 0.384034 0.759988 1.017301 11.00000 -1.50000 AFIX 0 C13 1 0.375333 0.917067 0.707568 11.00000 0.03339 0.03389 = 0.03028 -0.00022 0.00912 0.00458 AFIX 13 H13 2 0.364581 0.845074 0.682868 11.00000 -1.20000 AFIX 0 C14 1 0.322942 0.978583 0.709494 11.00000 0.03558 0.04118 = 0.03691 0.00689 0.01008 0.01009 AFIX 137 H14A 2 0.301111 0.991811 0.658893 11.00000 -1.50000 H14B 2 0.332518 1.048564 0.734943 11.00000 -1.50000 H14C 2 0.301770 0.934624 0.735877 11.00000 -1.50000 AFIX 0 C15 1 0.407098 0.979848 0.662584 11.00000 0.04646 0.05542 = 0.04152 0.00783 0.02059 0.00561 AFIX 137 H15A 2 0.384678 0.987852 0.611744 11.00000 -1.50000 H15B 2 0.440586 0.939953 0.662533 11.00000 -1.50000 H15C 2 0.416542 1.052278 0.684431 11.00000 -1.50000 AFIX 0 C16 1 0.315225 0.479540 0.681681 11.00000 0.02729 0.03307 = 0.02320 -0.00391 0.00723 -0.00925 C17 1 0.344326 0.388533 0.715578 11.00000 0.03437 0.03149 = 0.02961 0.00002 0.00652 -0.00956 C18 1 0.333539 0.288580 0.679039 11.00000 0.04286 0.03152 = 0.04275 -0.00364 0.01535 -0.00984 AFIX 43 H18 2 0.353507 0.225627 0.700091 11.00000 -1.20000 AFIX 0 C19 1 0.294191 0.279644 0.612573 11.00000 0.04586 0.04347 = 0.03760 -0.01663 0.01903 -0.01870 AFIX 43 H19 2 0.287039 0.210813 0.588606 11.00000 -1.20000 AFIX 0 C20 1 0.265469 0.370498 0.581279 11.00000 0.03631 0.05352 = 0.02694 -0.01119 0.01002 -0.01847 AFIX 43 H20 2 0.238262 0.362972 0.535961 11.00000 -1.20000 AFIX 0 C21 1 0.275082 0.473553 0.614104 11.00000 0.02567 0.04477 = 0.02307 -0.00623 0.00626 -0.01153 PART 1 21 C22A 1 0.379044 0.396698 0.795500 21.00000 0.04013 0.03046 = 0.03257 0.00307 0.00075 -0.00374 AFIX 13 H22A 2 0.397387 0.469677 0.801858 21.00000 -1.20000 AFIX 0 C23A 1 0.423634 0.308847 0.810325 21.00000 0.05368 0.05002 = 0.07174 -0.00014 -0.01461 0.01140 AFIX 137 H23A 2 0.446697 0.316757 0.860814 21.00000 -1.50000 H23B 2 0.446036 0.317281 0.775228 21.00000 -1.50000 H23C 2 0.406675 0.236340 0.804409 21.00000 -1.50000 AFIX 0 C24A 1 0.344288 0.388984 0.850861 21.00000 0.07694 0.07038 = 0.02821 0.00809 0.00575 -0.01716 AFIX 137 H24A 2 0.368183 0.386003 0.901122 21.00000 -1.50000 H24B 2 0.321848 0.322773 0.841090 21.00000 -1.50000 H24C 2 0.320557 0.453233 0.845854 21.00000 -1.50000 AFIX 0 PART 2 -21 C22B 1 0.390719 0.385707 0.786681 -21.00000 0.04013 0.03046 = 0.03257 0.00307 0.00075 -0.00374 AFIX 13 H22B 2 0.398214 0.463103 0.803285 -21.00000 -1.20000 AFIX 0 C23B 1 0.445003 0.336983 0.780464 -21.00000 0.05368 0.05002 = 0.07174 -0.00014 -0.01461 0.01140 AFIX 137 H23D 2 0.472688 0.346702 0.827373 -21.00000 -1.50000 H23E 2 0.456813 0.374181 0.740970 -21.00000 -1.50000 H23F 2 0.440222 0.258905 0.769074 -21.00000 -1.50000 AFIX 0 C24B 1 0.369618 0.327386 0.845908 -21.00000 0.07694 0.07038 = 0.02821 0.00809 0.00575 -0.01716 AFIX 137 H24D 2 0.395364 0.338404 0.894297 -21.00000 -1.50000 H24E 2 0.366059 0.249079 0.834838 -21.00000 -1.50000 H24F 2 0.333904 0.357290 0.846553 -21.00000 -1.50000 AFIX 0 PART 0 C25 1 0.241689 0.570830 0.577141 11.00000 0.02969 0.05487 = 0.02790 0.00077 0.00156 -0.00627 AFIX 13 H25 2 0.258505 0.638869 0.602755 11.00000 -1.20000 AFIX 0 C26 1 0.240901 0.579578 0.495328 11.00000 0.03894 0.07789 = 0.02887 0.00575 -0.00080 -0.00893 AFIX 137 H26A 2 0.221373 0.646023 0.474370 11.00000 -1.50000 H26B 2 0.222384 0.515630 0.468744 11.00000 -1.50000 H26C 2 0.278444 0.582674 0.490554 11.00000 -1.50000 AFIX 0 C27 1 0.182390 0.563223 0.583602 11.00000 0.03080 0.07579 = 0.04332 0.00190 0.00339 -0.00086 AFIX 137 H27A 2 0.161732 0.626931 0.559818 11.00000 -1.50000 H27B 2 0.182358 0.561467 0.635849 11.00000 -1.50000 H27C 2 0.165410 0.496439 0.559242 11.00000 -1.50000 AFIX 0 HKLF 5 REM MM3C in C2/c REM wR2 = 0.066083, GooF = S = 1.05940, Restrained GooF = 1.05940 for all data REM R1 = 0.033731 for 18656 Fo > 4sig(Fo) and 0.043609 for all 21362 data REM 317 parameters refined using 5 restraints END WGHT 0.0153 9.6446 REM Highest difference peak 1.232, deepest hole -0.705, 1-sigma level 0.089 Q1 1 0.3145 0.8810 0.7983 11.00000 0.05 1.23 Q2 1 0.3072 0.3808 0.7818 11.00000 0.05 1.23 Q3 1 0.3617 0.8372 0.9320 11.00000 0.05 1.14 Q4 1 0.3544 0.3343 0.9140 11.00000 0.05 1.08 Q5 1 0.4409 1.1391 0.7079 11.00000 0.05 0.50 Q6 1 0.4122 0.6184 0.5507 11.00000 0.05 0.44 Q7 1 0.3877 0.5780 0.5686 11.00000 0.05 0.40 Q8 1 0.3645 0.3888 0.7586 11.00000 0.05 0.39 Q9 1 0.4266 0.9320 0.8023 11.00000 0.05 0.38 Q10 1 0.4798 0.5923 0.6908 11.00000 0.05 0.37 Q11 1 0.4155 0.7804 0.9152 11.00000 0.05 0.36 Q12 1 0.3733 0.6667 0.5600 11.00000 0.05 0.36 Q13 1 0.5155 0.5781 0.6527 11.00000 0.05 0.36 Q14 1 0.3022 0.6067 0.7292 11.00000 0.05 0.36 Q15 1 0.2959 0.4862 0.6407 11.00000 0.05 0.36 Q16 1 0.3436 0.3421 0.6917 11.00000 0.05 0.35 Q17 1 0.3992 0.6217 0.5901 11.00000 0.05 0.35 Q18 1 0.2878 0.6772 0.7678 11.00000 0.05 0.34 Q19 1 0.3725 0.7448 0.5819 11.00000 0.05 0.34 Q20 1 0.4074 0.6160 0.7719 11.00000 0.05 0.33 ; _shelx_res_checksum 88435 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 I1 I 0.39135(2) 0.66658(2) 0.57634(2) 0.03267(4) Uani 1 1 d . . . . . Pd1 Pd 0.43899(2) 0.61869(2) 0.71060(2) 0.02139(3) Uani 1 1 d . . . . . O1 O 0.51218(6) 0.58558(16) 0.68573(9) 0.0283(3) Uani 1 1 d D . . . . H1A H 0.5181(16) 0.625(3) 0.6547(18) 0.034 Uiso 0.74(5) 1 d D U P A 1 H1B H 0.511(5) 0.531(6) 0.660(5) 0.034 Uiso 0.26(5) 1 d D U P A 2 N1 N 0.36047(7) 0.72186(16) 0.78379(10) 0.0251(3) Uani 1 1 d . . . . . C1 C 0.37092(8) 0.64105(18) 0.73967(11) 0.0234(4) Uani 1 1 d . . . . . N2 N 0.32365(7) 0.58229(16) 0.72055(10) 0.0259(4) Uani 1 1 d . . . . . C2 C 0.28455(9) 0.6283(2) 0.75156(13) 0.0331(5) Uani 1 1 d . . . . . H2 H 0.248387 0.602474 0.745986 0.040 Uiso 1 1 calc R U . . . C3 C 0.30720(9) 0.7154(2) 0.79060(14) 0.0319(5) Uani 1 1 d . . . . . H3 H 0.290269 0.763553 0.817691 0.038 Uiso 1 1 calc R U . . . C4 C 0.39943(8) 0.80055(19) 0.82344(12) 0.0255(4) Uani 1 1 d . . . . . C5 C 0.42514(9) 0.7789(2) 0.89798(12) 0.0291(4) Uani 1 1 d . . . . . C6 C 0.46169(11) 0.8576(2) 0.93508(14) 0.0384(6) Uani 1 1 d . . . . . H6 H 0.480552 0.845875 0.985312 0.046 Uiso 1 1 calc R U . . . C7 C 0.47106(12) 0.9520(3) 0.90035(16) 0.0440(7) Uani 1 1 d . . . . . H7 H 0.496097 1.004582 0.927001 0.053 Uiso 1 1 calc R U . . . C8 C 0.44441(11) 0.9713(2) 0.82702(15) 0.0382(6) Uani 1 1 d . . . . . H8 H 0.451219 1.037105 0.804069 0.046 Uiso 1 1 calc R U . . . C9 C 0.40770(9) 0.8951(2) 0.78656(13) 0.0288(4) Uani 1 1 d . . . . . C10 C 0.41283(10) 0.6776(2) 0.93816(13) 0.0338(5) Uani 1 1 d . . . . . H10 H 0.397443 0.620548 0.900349 0.041 Uiso 1 1 calc R U . . . C11 C 0.46315(12) 0.6301(3) 0.99238(18) 0.0527(8) Uani 1 1 d . . . . . H11A H 0.453431 0.561141 1.012351 0.079 Uiso 1 1 calc R U . . . H11B H 0.476687 0.681836 1.032853 0.079 Uiso 1 1 calc R U . . . H11C H 0.491645 0.616609 0.966754 0.079 Uiso 1 1 calc R U . . . C12 C 0.37008(13) 0.7030(3) 0.98056(19) 0.0518(8) Uani 1 1 d . . . . . H12A H 0.362490 0.636739 1.005533 0.078 Uiso 1 1 calc R U . . . H12B H 0.336389 0.728381 0.945951 0.078 Uiso 1 1 calc R U . . . H12C H 0.384034 0.759988 1.017301 0.078 Uiso 1 1 calc R U . . . C13 C 0.37533(10) 0.9171(2) 0.70757(13) 0.0324(5) Uani 1 1 d . . . . . H13 H 0.364581 0.845074 0.682868 0.039 Uiso 1 1 calc R U . . . C14 C 0.32294(11) 0.9786(2) 0.70949(15) 0.0378(6) Uani 1 1 d . . . . . H14A H 0.301111 0.991811 0.658893 0.057 Uiso 1 1 calc R U . . . H14B H 0.332518 1.048564 0.734943 0.057 Uiso 1 1 calc R U . . . H14C H 0.301770 0.934624 0.735877 0.057 Uiso 1 1 calc R U . . . C15 C 0.40710(12) 0.9798(3) 0.66258(17) 0.0461(7) Uani 1 1 d . . . . . H15A H 0.384678 0.987852 0.611744 0.069 Uiso 1 1 calc R U . . . H15B H 0.440586 0.939953 0.662533 0.069 Uiso 1 1 calc R U . . . H15C H 0.416542 1.052278 0.684431 0.069 Uiso 1 1 calc R U . . . C16 C 0.31523(9) 0.4795(2) 0.68168(12) 0.0277(4) Uani 1 1 d . . . . . C17 C 0.34433(10) 0.3885(2) 0.71558(13) 0.0322(5) Uani 1 1 d D . . . . C18 C 0.33354(12) 0.2886(2) 0.67904(16) 0.0383(6) Uani 1 1 d . . . . . H18 H 0.353507 0.225627 0.700091 0.046 Uiso 1 1 calc R U . . . C19 C 0.29419(12) 0.2796(2) 0.61257(15) 0.0408(6) Uani 1 1 d . . . . . H19 H 0.287039 0.210813 0.588606 0.049 Uiso 1 1 calc R U . . . C20 C 0.26547(11) 0.3705(2) 0.58128(14) 0.0386(6) Uani 1 1 d . . . . . H20 H 0.238262 0.362972 0.535961 0.046 Uiso 1 1 calc R U . . . C21 C 0.27508(9) 0.4736(2) 0.61410(12) 0.0312(5) Uani 1 1 d . . . . . C22A C 0.3790(2) 0.3967(6) 0.7955(2) 0.0360(12) Uani 0.591(5) 1 d D . P B 1 H22A H 0.397387 0.469677 0.801858 0.043 Uiso 0.591(5) 1 calc R U P B 1 C23A C 0.4236(3) 0.3088(5) 0.8103(4) 0.0642(18) Uani 0.591(5) 1 d D . P B 1 H23A H 0.446697 0.316757 0.860814 0.096 Uiso 0.591(5) 1 calc R U P B 1 H23B H 0.446036 0.317281 0.775228 0.096 Uiso 0.591(5) 1 calc R U P B 1 H23C H 0.406675 0.236340 0.804409 0.096 Uiso 0.591(5) 1 calc R U P B 1 C24A C 0.3443(3) 0.3890(6) 0.8509(3) 0.0600(15) Uani 0.591(5) 1 d D . P B 1 H24A H 0.368183 0.386003 0.901122 0.090 Uiso 0.591(5) 1 calc R U P B 1 H24B H 0.321848 0.322773 0.841090 0.090 Uiso 0.591(5) 1 calc R U P B 1 H24C H 0.320557 0.453233 0.845854 0.090 Uiso 0.591(5) 1 calc R U P B 1 C22B C 0.3907(3) 0.3857(10) 0.7867(3) 0.0360(12) Uani 0.409(5) 1 d D . P B 2 H22B H 0.398214 0.463103 0.803285 0.043 Uiso 0.409(5) 1 calc R U P B 2 C23B C 0.4450(4) 0.3370(9) 0.7805(6) 0.0642(18) Uani 0.409(5) 1 d D . P B 2 H23D H 0.472688 0.346702 0.827373 0.096 Uiso 0.409(5) 1 calc R U P B 2 H23E H 0.456813 0.374181 0.740970 0.096 Uiso 0.409(5) 1 calc R U P B 2 H23F H 0.440222 0.258905 0.769074 0.096 Uiso 0.409(5) 1 calc R U P B 2 C24B C 0.3696(4) 0.3274(9) 0.8459(4) 0.0600(15) Uani 0.409(5) 1 d D . P B 2 H24D H 0.395364 0.338404 0.894297 0.090 Uiso 0.409(5) 1 calc R U P B 2 H24E H 0.366059 0.249079 0.834838 0.090 Uiso 0.409(5) 1 calc R U P B 2 H24F H 0.333904 0.357290 0.846553 0.090 Uiso 0.409(5) 1 calc R U P B 2 C25 C 0.24169(10) 0.5708(3) 0.57714(14) 0.0386(6) Uani 1 1 d . . . . . H25 H 0.258505 0.638869 0.602755 0.046 Uiso 1 1 calc R U . . . C26 C 0.24090(12) 0.5796(3) 0.49533(15) 0.0503(8) Uani 1 1 d . . . . . H26A H 0.221373 0.646023 0.474370 0.076 Uiso 1 1 calc R U . . . H26B H 0.222384 0.515630 0.468744 0.076 Uiso 1 1 calc R U . . . H26C H 0.278444 0.582674 0.490554 0.076 Uiso 1 1 calc R U . . . C27 C 0.18239(11) 0.5632(3) 0.58360(17) 0.0511(8) Uani 1 1 d . . . . . H27A H 0.161732 0.626931 0.559818 0.077 Uiso 1 1 calc R U . . . H27B H 0.182358 0.561467 0.635849 0.077 Uiso 1 1 calc R U . . . H27C H 0.165410 0.496439 0.559242 0.077 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 I1 0.02721(7) 0.04827(9) 0.02177(6) 0.00137(6) 0.00497(5) 0.00399(6) Pd1 0.01875(6) 0.02443(7) 0.02062(6) -0.00199(6) 0.00442(5) -0.00077(6) O1 0.0214(7) 0.0382(9) 0.0251(7) -0.0005(7) 0.0057(6) 0.0002(7) N1 0.0202(8) 0.0299(9) 0.0255(8) -0.0045(7) 0.0062(6) -0.0009(7) C1 0.0215(9) 0.0274(10) 0.0204(8) -0.0007(7) 0.0036(7) -0.0019(7) N2 0.0224(8) 0.0323(9) 0.0228(8) -0.0031(7) 0.0056(6) -0.0055(7) C2 0.0229(10) 0.0455(14) 0.0330(11) -0.0055(10) 0.0108(8) -0.0070(9) C3 0.0235(10) 0.0405(12) 0.0342(11) -0.0060(10) 0.0123(8) -0.0018(9) C4 0.0203(9) 0.0289(10) 0.0266(9) -0.0068(8) 0.0051(7) 0.0006(8) C5 0.0260(10) 0.0345(11) 0.0260(10) -0.0058(9) 0.0055(8) 0.0024(9) C6 0.0359(13) 0.0468(15) 0.0292(11) -0.0109(11) 0.0025(9) -0.0019(11) C7 0.0440(15) 0.0451(16) 0.0410(14) -0.0188(12) 0.0077(11) -0.0142(12) C8 0.0425(14) 0.0315(12) 0.0415(14) -0.0079(11) 0.0127(11) -0.0072(11) C9 0.0260(10) 0.0305(11) 0.0305(10) -0.0046(9) 0.0083(8) 0.0010(8) C10 0.0326(12) 0.0400(13) 0.0288(11) 0.0012(10) 0.0079(9) 0.0059(10) C11 0.0410(15) 0.072(2) 0.0479(16) 0.0229(16) 0.0169(13) 0.0168(15) C12 0.0450(17) 0.066(2) 0.0520(17) 0.0116(17) 0.0272(14) 0.0150(15) C13 0.0334(12) 0.0339(12) 0.0303(11) -0.0002(9) 0.0091(9) 0.0046(10) C14 0.0356(13) 0.0412(14) 0.0369(13) 0.0069(11) 0.0101(10) 0.0101(11) C15 0.0465(16) 0.0554(18) 0.0415(14) 0.0078(13) 0.0206(12) 0.0056(14) C16 0.0273(10) 0.0331(11) 0.0232(9) -0.0039(8) 0.0072(8) -0.0092(9) C17 0.0344(12) 0.0315(11) 0.0296(11) 0.0000(9) 0.0065(9) -0.0096(10) C18 0.0429(14) 0.0315(12) 0.0427(14) -0.0036(11) 0.0153(11) -0.0098(11) C19 0.0459(15) 0.0435(15) 0.0376(13) -0.0166(12) 0.0190(11) -0.0187(12) C20 0.0363(13) 0.0535(16) 0.0269(11) -0.0112(11) 0.0100(9) -0.0185(12) C21 0.0257(10) 0.0448(14) 0.0231(9) -0.0062(9) 0.0063(8) -0.0115(10) C22A 0.040(2) 0.030(2) 0.0326(15) 0.0031(15) 0.0007(15) -0.004(2) C23A 0.054(4) 0.050(3) 0.072(4) 0.000(3) -0.015(3) 0.011(3) C24A 0.077(4) 0.070(4) 0.0282(17) 0.008(2) 0.006(2) -0.017(3) C22B 0.040(2) 0.030(2) 0.0326(15) 0.0031(15) 0.0007(15) -0.004(2) C23B 0.054(4) 0.050(3) 0.072(4) 0.000(3) -0.015(3) 0.011(3) C24B 0.077(4) 0.070(4) 0.0282(17) 0.008(2) 0.006(2) -0.017(3) C25 0.0297(12) 0.0549(16) 0.0279(11) 0.0008(11) 0.0016(9) -0.0063(11) C26 0.0389(15) 0.078(2) 0.0289(12) 0.0057(14) -0.0008(10) -0.0089(15) C27 0.0308(13) 0.076(2) 0.0433(15) 0.0019(15) 0.0034(11) -0.0009(14) 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' 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' I I -0.4742 1.8119 '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 O1 97.05(7) . 2_656 ? C1 Pd1 O1 175.65(8) . . ? O1 Pd1 O1 79.55(7) 2_656 . ? C1 Pd1 I1 90.93(6) . . ? O1 Pd1 I1 171.49(5) 2_656 . ? O1 Pd1 I1 92.61(5) . . ? C1 Pd1 Pd1 135.92(6) . 2_656 ? O1 Pd1 Pd1 42.16(4) 2_656 2_656 ? O1 Pd1 Pd1 41.86(4) . 2_656 ? I1 Pd1 Pd1 129.334(9) . 2_656 ? Pd1 O1 Pd1 95.98(7) 2_656 . ? Pd1 O1 H1A 113(3) 2_656 . ? Pd1 O1 H1A 113(3) . . ? Pd1 O1 H1B 130(8) 2_656 . ? Pd1 O1 H1B 113(8) . . ? C1 N1 C3 111.21(18) . . ? C1 N1 C4 125.79(17) . . ? C3 N1 C4 122.86(18) . . ? N1 C1 N2 104.31(18) . . ? N1 C1 Pd1 126.57(15) . . ? N2 C1 Pd1 129.12(16) . . ? C1 N2 C2 110.47(19) . . ? C1 N2 C16 126.73(19) . . ? C2 N2 C16 122.41(19) . . ? C3 C2 N2 107.5(2) . . ? C3 C2 H2 126.3 . . ? N2 C2 H2 126.3 . . ? C2 C3 N1 106.5(2) . . ? C2 C3 H3 126.7 . . ? N1 C3 H3 126.7 . . ? C9 C4 C5 124.0(2) . . ? C9 C4 N1 118.1(2) . . ? C5 C4 N1 117.8(2) . . ? C6 C5 C4 116.4(2) . . ? C6 C5 C10 120.7(2) . . ? C4 C5 C10 122.9(2) . . ? C7 C6 C5 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 120.8(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C9 120.7(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C4 C9 C8 116.8(2) . . ? C4 C9 C13 121.2(2) . . ? C8 C9 C13 121.9(2) . . ? C5 C10 C11 113.4(2) . . ? C5 C10 C12 110.8(2) . . ? C11 C10 C12 108.3(2) . . ? C5 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? C12 C10 H10 108.1 . . ? 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 . . ? C15 C13 C9 113.6(2) . . ? C15 C13 C14 110.6(2) . . ? C9 C13 C14 108.4(2) . . ? C15 C13 H13 108.0 . . ? C9 C13 H13 108.0 . . ? C14 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 122.9(2) . . ? C17 C16 N2 118.4(2) . . ? C21 C16 N2 118.6(2) . . ? C18 C17 C16 117.6(2) . . ? C18 C17 C22A 121.8(4) . . ? C16 C17 C22A 119.7(3) . . ? C18 C17 C22B 114.6(5) . . ? C16 C17 C22B 127.6(5) . . ? C19 C18 C17 121.0(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 122.0(2) . . ? C19 C20 H20 119.0 . . ? C21 C20 H20 119.0 . . ? C20 C21 C16 116.5(2) . . ? C20 C21 C25 119.6(2) . . ? C16 C21 C25 123.9(2) . . ? C24A C22A C17 111.9(4) . . ? C24A C22A C23A 111.2(6) . . ? C17 C22A C23A 110.0(5) . . ? C24A C22A H22A 107.9 . . ? C17 C22A H22A 107.9 . . ? C23A C22A H22A 107.9 . . ? C22A C23A H23A 109.5 . . ? C22A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? C22A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? C22A C24A H24A 109.5 . . ? C22A C24A H24B 109.5 . . ? H24A C24A H24B 109.5 . . ? C22A C24A H24C 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C24B C22B C23B 111.4(8) . . ? C24B C22B C17 107.9(6) . . ? C23B C22B C17 116.4(6) . . ? C24B C22B H22B 106.9 . . ? C23B C22B H22B 106.9 . . ? C17 C22B H22B 106.9 . . ? C22B C23B H23D 109.5 . . ? C22B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C22B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C22B C24B H24D 109.5 . . ? C22B C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C22B C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? C21 C25 C26 111.8(2) . . ? C21 C25 C27 110.9(2) . . ? C26 C25 C27 108.8(2) . . ? C21 C25 H25 108.4 . . ? C26 C25 H25 108.4 . . ? C27 C25 H25 108.4 . . ? 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 . . ? 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 I1 Pd1 2.5616(2) . ? Pd1 C1 1.960(2) . ? Pd1 O1 2.0561(16) 2_656 ? Pd1 O1 2.0681(16) . ? Pd1 Pd1 3.0644(3) 2_656 ? O1 H1A 0.80(2) . ? O1 H1B 0.82(3) . ? N1 C1 1.359(3) . ? N1 C3 1.392(3) . ? N1 C4 1.441(3) . ? C1 N2 1.364(3) . ? N2 C2 1.392(3) . ? N2 C16 1.441(3) . ? C2 C3 1.336(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.392(3) . ? C4 C5 1.406(3) . ? C5 C6 1.391(3) . ? C5 C10 1.525(4) . ? C6 C7 1.378(4) . ? C6 H6 0.9500 . ? C7 C8 1.386(4) . ? C7 H7 0.9500 . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C13 1.519(3) . ? C10 C11 1.526(4) . ? C10 C12 1.533(4) . ? 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 C15 1.518(4) . ? C13 C14 1.536(3) . ? 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 1.395(4) . ? C16 C21 1.406(3) . ? C17 C18 1.394(4) . ? C17 C22A 1.532(4) . ? C17 C22B 1.533(4) . ? C18 C19 1.384(4) . ? C18 H18 0.9500 . ? C19 C20 1.375(4) . ? C19 H19 0.9500 . ? C20 C21 1.397(4) . ? C20 H20 0.9500 . ? C21 C25 1.520(4) . ? C22A C24A 1.529(6) . ? C22A C23A 1.533(6) . ? C22A H22A 1.0000 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C22B C24B 1.529(6) . ? C22B C23B 1.532(7) . ? C22B H22B 1.0000 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25 C26 1.533(4) . ? C25 C27 1.543(4) . ? 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 . ? 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 -1.5(2) . . . . ? C4 N1 C1 N2 174.3(2) . . . . ? C3 N1 C1 Pd1 177.75(17) . . . . ? C4 N1 C1 Pd1 -6.4(3) . . . . ? N1 C1 N2 C2 1.2(2) . . . . ? Pd1 C1 N2 C2 -178.05(17) . . . . ? N1 C1 N2 C16 -171.6(2) . . . . ? Pd1 C1 N2 C16 9.1(3) . . . . ? C1 N2 C2 C3 -0.4(3) . . . . ? C16 N2 C2 C3 172.7(2) . . . . ? N2 C2 C3 N1 -0.5(3) . . . . ? C1 N1 C3 C2 1.3(3) . . . . ? C4 N1 C3 C2 -174.7(2) . . . . ? C1 N1 C4 C9 85.9(3) . . . . ? C3 N1 C4 C9 -98.7(3) . . . . ? C1 N1 C4 C5 -96.6(3) . . . . ? C3 N1 C4 C5 78.8(3) . . . . ? C9 C4 C5 C6 -1.4(3) . . . . ? N1 C4 C5 C6 -178.7(2) . . . . ? C9 C4 C5 C10 176.4(2) . . . . ? N1 C4 C5 C10 -1.0(3) . . . . ? C4 C5 C6 C7 1.1(4) . . . . ? C10 C5 C6 C7 -176.7(2) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C5 C4 C9 C8 0.8(3) . . . . ? N1 C4 C9 C8 178.1(2) . . . . ? C5 C4 C9 C13 -175.3(2) . . . . ? N1 C4 C9 C13 2.0(3) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C7 C8 C9 C13 176.2(2) . . . . ? C6 C5 C10 C11 -39.9(3) . . . . ? C4 C5 C10 C11 142.4(2) . . . . ? C6 C5 C10 C12 82.1(3) . . . . ? C4 C5 C10 C12 -95.6(3) . . . . ? C4 C9 C13 C15 -147.3(2) . . . . ? C8 C9 C13 C15 36.8(3) . . . . ? C4 C9 C13 C14 89.3(3) . . . . ? C8 C9 C13 C14 -86.6(3) . . . . ? C1 N2 C16 C17 64.1(3) . . . . ? C2 N2 C16 C17 -107.9(3) . . . . ? C1 N2 C16 C21 -120.7(2) . . . . ? C2 N2 C16 C21 67.2(3) . . . . ? C21 C16 C17 C18 1.7(4) . . . . ? N2 C16 C17 C18 176.6(2) . . . . ? C21 C16 C17 C22A -168.1(3) . . . . ? N2 C16 C17 C22A 6.8(4) . . . . ? C21 C16 C17 C22B 176.6(4) . . . . ? N2 C16 C17 C22B -8.5(5) . . . . ? C16 C17 C18 C19 -1.9(4) . . . . ? C22A C17 C18 C19 167.7(3) . . . . ? C22B C17 C18 C19 -177.5(4) . . . . ? C17 C18 C19 C20 0.7(4) . . . . ? C18 C19 C20 C21 0.8(4) . . . . ? C19 C20 C21 C16 -0.9(4) . . . . ? C19 C20 C21 C25 -179.5(2) . . . . ? C17 C16 C21 C20 -0.3(3) . . . . ? N2 C16 C21 C20 -175.2(2) . . . . ? C17 C16 C21 C25 178.2(2) . . . . ? N2 C16 C21 C25 3.3(3) . . . . ? C18 C17 C22A C24A -90.6(6) . . . . ? C16 C17 C22A C24A 78.8(6) . . . . ? C18 C17 C22A C23A 33.6(6) . . . . ? C16 C17 C22A C23A -157.1(4) . . . . ? C18 C17 C22B C24B -73.8(8) . . . . ? C16 C17 C22B C24B 111.2(7) . . . . ? C18 C17 C22B C23B 52.3(10) . . . . ? C16 C17 C22B C23B -122.8(8) . . . . ? C20 C21 C25 C26 -50.2(3) . . . . ? C16 C21 C25 C26 131.3(3) . . . . ? C20 C21 C25 C27 71.5(3) . . . . ? C16 C21 C25 C27 -107.0(3) . . . . ?