#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:34:55 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257389 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557749.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_1557749 loop_ _publ_author_name 'Baek, Doohyun' 'Ryu, Huijeong' 'Ryu, Ji Yeon' 'Lee, Junseong' 'Stoltz, Brian M.' 'Hong, Sukwon' _publ_section_title ; Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands ; _journal_issue 18 _journal_name_full 'Chemical Science' _journal_page_first 4602 _journal_page_last 4607 _journal_paper_doi 10.1039/D0SC00412J _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C26 H25 Cl2 F3 N2 Pd, C1 H2 Cl2' _chemical_formula_sum 'C27 H27 Cl4 F3 N2 Pd' _chemical_formula_weight 684.71 _chemical_name_systematic '((S)-3-(2,6-diethylbenzyl)-1-(5-(trifluoromethyl)pyridin-2-yl)-3,4-dihydroisoquinoline) palladium(II) chloride' _chemical_properties_physical Air-sensitive,Moisture-sensitive,Heat-sensitive _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _audit_update_record ; 2019-09-20 deposited with the CCDC. 2020-04-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3222(2) _cell_length_b 16.3645(5) _cell_length_c 22.9119(6) _cell_measurement_reflns_used 5617 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 19.77 _cell_measurement_theta_min 2.17 _cell_volume 2745.40(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0716 _diffrn_reflns_av_unetI/netI 0.0645 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 37246 _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 25.369 _diffrn_reflns_theta_min 2.170 _exptl_absorpt_coefficient_mu 1.104 _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.657 _exptl_crystal_description block _exptl_crystal_F_000 1272 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM, Hexane' _refine_diff_density_max 0.689 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.090 _refine_ls_abs_structure_details ; Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 5004 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0441 _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^)+(0.0560P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.1018 _reflns_Friedel_coverage 0.742 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.989 _reflns_number_gt 3907 _reflns_number_total 5004 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00412j2.cif _cod_data_source_block hsw41-1 _cod_depositor_comments ;Adding full bibliography for 1557749--1557750.cif. Adding full bibliography for 1557749--1557750.cif. ; _cod_database_code 1557749 _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL hsw41-1 in P2(1)2(1)2(1) CELL 0.71073 7.32220 16.36453 22.91190 90.0000 90.0000 90.0000 ZERR 4.00 0.00020 0.00045 0.00060 0.0000 0.0000 0.0000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C N F Cl Pd H UNIT 108 8 12 16 4 4 OMIT 0 1 1 L.S. 5 ACTA BOND FMAP 2 PLAN 5 TEMP 23.000 WGHT 0.056000 FVAR 0.08789 MOLE 1 PD1 5 0.326899 0.793746 0.995281 11.00000 0.02453 0.02174 = 0.03180 -0.00164 0.00003 -0.00154 CL2 4 0.344027 0.932602 1.001366 11.00000 0.04394 0.02437 = 0.04035 -0.00407 0.00151 -0.00101 N1 2 0.310550 0.671497 0.982854 11.00000 0.01756 0.02618 = 0.02997 -0.00713 0.00159 -0.00170 N2 2 0.333941 0.789626 0.907307 11.00000 0.01121 0.01750 = 0.02834 -0.00088 0.00525 0.00113 CL1 4 0.318100 0.784753 1.094852 11.00000 0.04382 0.03612 = 0.02869 -0.00445 0.00197 -0.00643 C12 1 0.150823 0.650121 0.798100 11.00000 0.03386 0.02165 = 0.02983 0.00303 0.00027 0.00236 AFIX 43 H12 6 0.087270 0.615214 0.822868 11.00000 -1.20000 AFIX 0 C15 1 0.333428 0.757573 0.724776 11.00000 0.02112 0.03268 = 0.03381 0.00315 0.00937 0.01294 AFIX 43 H15 6 0.394739 0.793239 0.699982 11.00000 -1.20000 AFIX 0 C14 1 0.217809 0.698476 0.701106 11.00000 0.02915 0.02856 = 0.02796 -0.00222 -0.00185 0.00835 AFIX 43 H14 6 0.202334 0.694770 0.660905 11.00000 -1.20000 AFIX 0 C7 1 0.301054 0.718400 0.884428 11.00000 0.01808 0.02137 = 0.03312 -0.00489 -0.00052 0.00333 C8 1 0.271774 0.707768 0.821200 11.00000 0.02184 0.02293 = 0.02871 -0.00372 0.00179 0.00788 C9 1 0.358552 0.764112 0.784311 11.00000 0.01466 0.02287 = 0.03421 0.00064 0.00394 0.01237 C13 1 0.125691 0.645037 0.738203 11.00000 0.03791 0.02262 = 0.03588 -0.00428 -0.00172 0.00075 AFIX 43 H13 6 0.047245 0.605906 0.722777 11.00000 -1.20000 AFIX 0 C1 1 0.299208 0.649325 0.925729 11.00000 0.02369 0.02045 = 0.02701 0.00067 -0.00177 0.00409 C11 1 0.368360 0.859114 0.867502 11.00000 0.02547 0.02043 = 0.03731 0.00064 -0.00117 -0.00552 AFIX 13 H11 6 0.449579 0.897298 0.887800 11.00000 -1.20000 AFIX 0 C10 1 0.467619 0.829410 0.813520 11.00000 0.01934 0.02504 = 0.03466 0.00590 0.00075 0.00616 AFIX 23 H10A 6 0.485936 0.874635 0.786787 11.00000 -1.20000 H10B 6 0.586475 0.808073 0.824353 11.00000 -1.20000 AFIX 0 C17 1 0.193724 0.954514 0.798942 11.00000 0.02526 0.01917 = 0.03819 0.00392 0.00569 0.00742 C16 1 0.185128 0.904906 0.855191 11.00000 0.02056 0.02962 = 0.03118 -0.00093 0.00349 -0.00010 AFIX 23 H16A 6 0.086802 0.865379 0.852376 11.00000 -1.20000 H16B 6 0.158217 0.941139 0.887574 11.00000 -1.20000 AFIX 0 C22 1 0.309133 1.021174 0.793701 11.00000 0.02548 0.02743 = 0.04415 0.00669 -0.00175 0.00926 C21 1 0.336526 1.056626 0.738311 11.00000 0.03059 0.02833 = 0.06364 0.01808 0.00642 -0.00728 AFIX 43 H21 6 0.417778 1.099973 0.734464 11.00000 -1.20000 AFIX 0 C19 1 0.119730 0.968141 0.696756 11.00000 0.04063 0.03854 = 0.04129 0.00069 -0.00180 0.01837 AFIX 43 H19 6 0.052908 0.951421 0.664369 11.00000 -1.20000 AFIX 0 C18 1 0.086559 0.930252 0.750397 11.00000 0.02552 0.02634 = 0.04316 0.00271 0.00628 0.00976 C20 1 0.245713 1.028448 0.690000 11.00000 0.04385 0.04025 = 0.05440 0.02095 0.01099 0.00433 AFIX 43 H20 6 0.269836 1.050177 0.653295 11.00000 -1.20000 AFIX 0 C4 1 0.319127 0.532403 1.009821 11.00000 0.02427 0.02822 = 0.03133 0.00151 -0.00456 -0.00857 C3 1 0.316636 0.508695 0.952262 11.00000 0.04229 0.02168 = 0.03758 0.00276 -0.00481 -0.00227 AFIX 43 H3 6 0.322033 0.453675 0.942249 11.00000 -1.20000 AFIX 0 C2 1 0.305945 0.568236 0.909496 11.00000 0.04318 0.02936 = 0.03066 -0.00311 0.00098 -0.00433 AFIX 43 H2 6 0.303336 0.553723 0.870260 11.00000 -1.20000 AFIX 0 C5 1 0.316959 0.614257 1.022969 11.00000 0.01975 0.02422 = 0.03496 -0.00003 -0.00476 -0.00046 AFIX 43 H5 6 0.320170 0.629842 1.061989 11.00000 -1.20000 AFIX 0 C26 1 0.328981 1.143584 0.860219 11.00000 0.04889 0.02546 = 0.05904 -0.00069 0.00848 -0.00179 AFIX 137 H26A 6 0.342397 1.179682 0.827471 11.00000 -1.50000 H26B 6 0.394270 1.165350 0.893061 11.00000 -1.50000 H26C 6 0.201938 1.138499 0.869914 11.00000 -1.50000 AFIX 0 C24 1 -0.189168 0.854166 0.705651 11.00000 0.04305 0.08102 = 0.04858 -0.01286 -0.00069 -0.01516 AFIX 137 H24A 6 -0.247918 0.904829 0.695973 11.00000 -1.50000 H24B 6 -0.279949 0.814088 0.715372 11.00000 -1.50000 H24C 6 -0.119235 0.835466 0.672823 11.00000 -1.50000 AFIX 0 C23 1 -0.063525 0.866974 0.757403 11.00000 0.02288 0.03485 = 0.05668 -0.00657 -0.00251 0.00732 AFIX 23 H23A 6 -0.006728 0.815023 0.766682 11.00000 -1.20000 H23B 6 -0.137799 0.882468 0.790666 11.00000 -1.20000 AFIX 0 C25 1 0.405885 1.059614 0.844647 11.00000 0.04232 0.03325 = 0.06870 0.01353 -0.01501 -0.01906 AFIX 23 H25A 6 0.534601 1.065038 0.835415 11.00000 -1.20000 H25B 6 0.395267 1.023911 0.878271 11.00000 -1.20000 AFIX 0 C6 1 0.329488 0.468584 1.056573 11.00000 0.04237 0.03394 = 0.03844 0.00489 -0.00283 -0.00557 F1 3 0.198192 0.412608 1.050858 11.00000 0.06476 0.03401 = 0.04706 0.01349 -0.00725 -0.02199 F3 3 0.313466 0.500077 1.110058 11.00000 0.05837 0.04194 = 0.03457 0.00874 -0.00339 -0.01707 F2 3 0.489103 0.428287 1.056084 11.00000 0.05435 0.05139 = 0.06161 0.01740 -0.00128 0.01230 CL3 4 0.988465 0.305091 0.943670 11.00000 0.11919 0.08015 = 0.06363 -0.00969 -0.01389 0.00310 CL4 4 0.599710 0.326336 0.925547 11.00000 0.11680 0.08319 = 0.05942 -0.02234 -0.00077 0.01740 C27 1 0.791574 0.350724 0.968798 11.00000 0.13335 0.07372 = 0.07220 -0.04424 0.02440 -0.03735 AFIX 23 H27A 6 0.808140 0.409532 0.969084 11.00000 -1.20000 H27B 6 0.769277 0.333279 1.008626 11.00000 -1.20000 AFIX 0 HKLF 4 REM hsw41-1 in P2(1)2(1)2(1) REM R1 = 0.0441 for 3907 Fo > 4sig(Fo) and 0.0676 for all 5004 data REM 336 parameters refined using 0 restraints END WGHT 0.0460 0.4435 REM Highest difference peak 0.689, deepest hole -0.472, 1-sigma level 0.090 Q1 1 0.3432 0.7384 1.0458 11.00000 0.05 0.69 Q2 1 0.3431 0.7427 0.9439 11.00000 0.05 0.64 Q3 1 0.3421 0.8593 1.0467 11.00000 0.05 0.62 Q4 1 0.3372 0.8557 0.9481 11.00000 0.05 0.50 Q5 1 0.2793 0.7861 0.9040 11.00000 0.05 0.39 ; _shelx_res_checksum 9775 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 0.32690(8) 0.79375(3) 0.99528(2) 0.02602(18) Uani 1 1 d . . . . . Cl2 Cl 0.3440(3) 0.93260(10) 1.00137(9) 0.0362(4) Uani 1 1 d . . . . . N1 N 0.3106(8) 0.6715(4) 0.9829(2) 0.0246(14) Uani 1 1 d . . . . . N2 N 0.3339(8) 0.7896(4) 0.9073(2) 0.0190(12) Uani 1 1 d . . . . . Cl1 Cl 0.3181(3) 0.78475(13) 1.09485(7) 0.0362(5) Uani 1 1 d . . . . . C12 C 0.1508(11) 0.6501(4) 0.7981(3) 0.0284(18) Uani 1 1 d . . . . . H12 H 0.0873 0.6152 0.8229 0.034 Uiso 1 1 calc R U . . . C15 C 0.3334(11) 0.7576(4) 0.7248(3) 0.0292(18) Uani 1 1 d . . . . . H15 H 0.3947 0.7932 0.7000 0.035 Uiso 1 1 calc R U . . . C14 C 0.2178(10) 0.6985(5) 0.7011(3) 0.0286(18) Uani 1 1 d . . . . . H14 H 0.2023 0.6948 0.6609 0.034 Uiso 1 1 calc R U . . . C7 C 0.3011(10) 0.7184(4) 0.8844(3) 0.0242(17) Uani 1 1 d . . . . . C8 C 0.2718(9) 0.7078(5) 0.8212(3) 0.0245(17) Uani 1 1 d . . . . . C9 C 0.3586(9) 0.7641(4) 0.7843(3) 0.0239(18) Uani 1 1 d . . . . . C13 C 0.1257(11) 0.6450(5) 0.7382(3) 0.032(2) Uani 1 1 d . . . . . H13 H 0.0472 0.6059 0.7228 0.039 Uiso 1 1 calc R U . . . C1 C 0.2992(10) 0.6493(4) 0.9257(3) 0.0237(17) Uani 1 1 d . . . . . C11 C 0.3684(10) 0.8591(4) 0.8675(3) 0.0277(19) Uani 1 1 d . . . . . H11 H 0.4496 0.8973 0.8878 0.033 Uiso 1 1 calc R U . . . C10 C 0.4676(10) 0.8294(4) 0.8135(3) 0.0263(18) Uani 1 1 d . . . . . H10A H 0.4859 0.8746 0.7868 0.032 Uiso 1 1 calc R U . . . H10B H 0.5865 0.8081 0.8244 0.032 Uiso 1 1 calc R U . . . C17 C 0.1937(12) 0.9545(5) 0.7989(3) 0.0275(18) Uani 1 1 d . . . . . C16 C 0.1851(11) 0.9049(4) 0.8552(3) 0.0271(17) Uani 1 1 d . . . . . H16A H 0.0868 0.8654 0.8524 0.033 Uiso 1 1 calc R U . . . H16B H 0.1582 0.9411 0.8876 0.033 Uiso 1 1 calc R U . . . C22 C 0.3091(12) 1.0212(5) 0.7937(3) 0.0324(19) Uani 1 1 d . . . . . C21 C 0.3365(13) 1.0566(5) 0.7383(4) 0.041(2) Uani 1 1 d . . . . . H21 H 0.4178 1.1000 0.7345 0.049 Uiso 1 1 calc R U . . . C19 C 0.1197(12) 0.9681(5) 0.6968(4) 0.040(2) Uani 1 1 d . . . . . H19 H 0.0529 0.9514 0.6644 0.048 Uiso 1 1 calc R U . . . C18 C 0.0866(10) 0.9303(5) 0.7504(4) 0.032(2) Uani 1 1 d . . . . . C20 C 0.2457(12) 1.0284(6) 0.6900(4) 0.046(3) Uani 1 1 d . . . . . H20 H 0.2698 1.0502 0.6533 0.055 Uiso 1 1 calc R U . . . C4 C 0.3191(10) 0.5324(4) 1.0098(3) 0.0279(16) Uani 1 1 d . . . . . C3 C 0.3166(12) 0.5087(5) 0.9523(3) 0.0338(19) Uani 1 1 d . . . . . H3 H 0.3220 0.4537 0.9422 0.041 Uiso 1 1 calc R U . . . C2 C 0.3059(12) 0.5682(5) 0.9095(3) 0.0344(19) Uani 1 1 d . . . . . H2 H 0.3033 0.5537 0.8703 0.041 Uiso 1 1 calc R U . . . C5 C 0.3170(10) 0.6143(4) 1.0230(3) 0.0263(17) Uani 1 1 d . . . . . H5 H 0.3202 0.6298 1.0620 0.032 Uiso 1 1 calc R U . . . C26 C 0.3290(13) 1.1436(5) 0.8602(3) 0.044(2) Uani 1 1 d . . . . . H26A H 0.3424 1.1797 0.8275 0.067 Uiso 1 1 calc R U . . . H26B H 0.3943 1.1654 0.8931 0.067 Uiso 1 1 calc R U . . . H26C H 0.2019 1.1385 0.8699 0.067 Uiso 1 1 calc R U . . . C24 C -0.1892(14) 0.8542(6) 0.7057(3) 0.058(3) Uani 1 1 d . . . . . H24A H -0.2479 0.9048 0.6960 0.086 Uiso 1 1 calc R U . . . H24B H -0.2799 0.8141 0.7154 0.086 Uiso 1 1 calc R U . . . H24C H -0.1192 0.8355 0.6728 0.086 Uiso 1 1 calc R U . . . C23 C -0.0635(10) 0.8670(5) 0.7574(4) 0.038(2) Uani 1 1 d . . . . . H23A H -0.0067 0.8150 0.7667 0.046 Uiso 1 1 calc R U . . . H23B H -0.1378 0.8825 0.7907 0.046 Uiso 1 1 calc R U . . . C25 C 0.4059(12) 1.0596(5) 0.8446(4) 0.048(2) Uani 1 1 d . . . . . H25A H 0.5346 1.0650 0.8354 0.058 Uiso 1 1 calc R U . . . H25B H 0.3953 1.0239 0.8783 0.058 Uiso 1 1 calc R U . . . C6 C 0.3295(14) 0.4686(5) 1.0566(3) 0.038(2) Uani 1 1 d . . . . . F1 F 0.1982(7) 0.4126(3) 1.05086(19) 0.0486(13) Uani 1 1 d . . . . . F3 F 0.3135(7) 0.5001(3) 1.11006(18) 0.0450(12) Uani 1 1 d . . . . . F2 F 0.4891(7) 0.4283(3) 1.0561(2) 0.0558(15) Uani 1 1 d . . . . . Cl3 Cl 0.9885(5) 0.3051(2) 0.94367(12) 0.0877(10) Uani 1 1 d . . . . . Cl4 Cl 0.5997(5) 0.32634(19) 0.92555(12) 0.0865(11) Uani 1 1 d . . . . . C27 C 0.7916(18) 0.3507(7) 0.9688(5) 0.093(4) Uani 1 1 d . . . . . H27A H 0.8081 0.4095 0.9691 0.112 Uiso 1 1 calc R U . . . H27B H 0.7693 0.3333 1.0086 0.112 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 0.0245(3) 0.0217(3) 0.0318(3) -0.0016(3) 0.0000(3) -0.0015(3) Cl2 0.0439(11) 0.0244(9) 0.0403(10) -0.0041(9) 0.0015(14) -0.0010(9) N1 0.018(3) 0.026(3) 0.030(3) -0.007(3) 0.002(3) -0.002(3) N2 0.011(3) 0.018(3) 0.028(3) -0.001(3) 0.005(3) 0.001(4) Cl1 0.0438(12) 0.0361(12) 0.0287(9) -0.0045(9) 0.0020(11) -0.0064(14) C12 0.034(5) 0.022(4) 0.030(4) 0.003(3) 0.000(4) 0.002(4) C15 0.021(4) 0.033(5) 0.034(4) 0.003(3) 0.009(4) 0.013(4) C14 0.029(5) 0.029(5) 0.028(4) -0.002(4) -0.002(3) 0.008(4) C7 0.018(4) 0.021(4) 0.033(4) -0.005(3) -0.001(3) 0.003(4) C8 0.022(4) 0.023(4) 0.029(4) -0.004(4) 0.002(3) 0.008(4) C9 0.015(4) 0.023(4) 0.034(4) 0.001(3) 0.004(3) 0.012(3) C13 0.038(5) 0.023(4) 0.036(4) -0.004(4) -0.002(4) 0.001(4) C1 0.024(4) 0.020(4) 0.027(4) 0.001(3) -0.002(4) 0.004(4) C11 0.025(5) 0.020(4) 0.037(4) 0.001(3) -0.001(3) -0.006(4) C10 0.019(4) 0.025(4) 0.035(4) 0.006(3) 0.001(4) 0.006(3) C17 0.025(5) 0.019(4) 0.038(4) 0.004(3) 0.006(4) 0.007(4) C16 0.021(4) 0.030(4) 0.031(4) -0.001(3) 0.003(4) 0.000(4) C22 0.025(5) 0.027(5) 0.044(5) 0.007(4) -0.002(4) 0.009(4) C21 0.031(5) 0.028(5) 0.064(6) 0.018(4) 0.006(5) -0.007(5) C19 0.041(6) 0.039(6) 0.041(5) 0.001(4) -0.002(4) 0.018(5) C18 0.026(5) 0.026(5) 0.043(5) 0.003(4) 0.006(4) 0.010(4) C20 0.044(6) 0.040(6) 0.054(6) 0.021(5) 0.011(5) 0.004(5) C4 0.024(4) 0.028(4) 0.031(4) 0.002(3) -0.005(4) -0.009(4) C3 0.042(5) 0.022(4) 0.038(4) 0.003(4) -0.005(5) -0.002(4) C2 0.043(5) 0.029(5) 0.031(4) -0.003(4) 0.001(4) -0.004(4) C5 0.020(4) 0.024(4) 0.035(4) 0.000(3) -0.005(4) 0.000(4) C26 0.049(5) 0.025(5) 0.059(5) -0.001(4) 0.008(5) -0.002(5) C24 0.043(6) 0.081(8) 0.049(5) -0.013(5) -0.001(5) -0.015(6) C23 0.023(4) 0.035(5) 0.057(5) -0.007(4) -0.003(4) 0.007(4) C25 0.042(6) 0.033(5) 0.069(6) 0.014(5) -0.015(5) -0.019(5) C6 0.042(5) 0.034(5) 0.038(5) 0.005(4) -0.003(5) -0.006(6) F1 0.065(3) 0.034(3) 0.047(3) 0.013(2) -0.007(3) -0.022(3) F3 0.058(3) 0.042(3) 0.035(2) 0.009(2) -0.003(3) -0.017(3) F2 0.054(4) 0.051(4) 0.062(3) 0.017(3) -0.001(3) 0.012(3) Cl3 0.119(3) 0.080(2) 0.0636(17) -0.0097(16) -0.0139(17) 0.003(2) Cl4 0.117(3) 0.083(2) 0.0594(17) -0.0223(16) -0.0008(17) 0.0174(19) C27 0.133(12) 0.074(8) 0.072(7) -0.044(6) 0.024(8) -0.037(8) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' H H 0.0000 0.0000 '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 N2 Pd1 N1 80.1(2) . . ? N2 Pd1 Cl2 95.34(17) . . ? N1 Pd1 Cl2 175.41(18) . . ? N2 Pd1 Cl1 174.39(16) . . ? N1 Pd1 Cl1 94.30(16) . . ? Cl2 Pd1 Cl1 90.27(8) . . ? C5 N1 C1 119.0(6) . . ? C5 N1 Pd1 127.2(5) . . ? C1 N1 Pd1 113.7(5) . . ? C7 N2 C11 118.2(5) . . ? C7 N2 Pd1 115.3(5) . . ? C11 N2 Pd1 126.5(4) . . ? C13 C12 C8 119.9(7) . . ? C9 C15 C14 121.2(7) . . ? C13 C14 C15 119.4(7) . . ? N2 C7 C1 115.5(6) . . ? N2 C7 C8 121.9(6) . . ? C1 C7 C8 122.6(6) . . ? C12 C8 C9 120.2(6) . . ? C12 C8 C7 122.9(7) . . ? C9 C8 C7 116.6(6) . . ? C15 C9 C8 118.9(7) . . ? C15 C9 C10 124.7(7) . . ? C8 C9 C10 116.3(6) . . ? C12 C13 C14 120.1(7) . . ? N1 C1 C2 120.9(6) . . ? N1 C1 C7 114.4(6) . . ? C2 C1 C7 124.4(6) . . ? N2 C11 C10 109.8(6) . . ? N2 C11 C16 109.5(6) . . ? C10 C11 C16 114.7(6) . . ? C9 C10 C11 109.8(6) . . ? C22 C17 C18 119.4(7) . . ? C22 C17 C16 121.2(7) . . ? C18 C17 C16 119.4(7) . . ? C17 C16 C11 111.9(6) . . ? C17 C22 C21 119.3(8) . . ? C17 C22 C25 123.3(7) . . ? C21 C22 C25 117.4(8) . . ? C20 C21 C22 121.3(8) . . ? C20 C19 C18 122.7(9) . . ? C19 C18 C17 118.0(7) . . ? C19 C18 C23 121.4(8) . . ? C17 C18 C23 120.6(7) . . ? C19 C20 C21 118.8(9) . . ? C5 C4 C3 119.1(7) . . ? C5 C4 C6 121.6(6) . . ? C3 C4 C6 119.3(7) . . ? C4 C3 C2 118.8(7) . . ? C1 C2 C3 119.2(7) . . ? N1 C5 C4 122.9(7) . . ? C24 C23 C18 116.8(8) . . ? C22 C25 C26 112.6(7) . . ? F1 C6 F3 107.0(7) . . ? F1 C6 F2 106.8(6) . . ? F3 C6 F2 105.9(7) . . ? F1 C6 C4 111.8(7) . . ? F3 C6 C4 112.5(7) . . ? F2 C6 C4 112.4(7) . . ? Cl3 C27 Cl4 112.4(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 N2 2.017(5) . ? Pd1 N1 2.024(6) . ? Pd1 Cl2 2.2800(18) . ? Pd1 Cl1 2.2870(17) . ? N1 C5 1.313(9) . ? N1 C1 1.361(8) . ? N2 C7 1.301(9) . ? N2 C11 1.479(9) . ? C12 C13 1.387(10) . ? C12 C8 1.398(10) . ? C15 C9 1.381(9) . ? C15 C14 1.395(10) . ? C14 C13 1.394(10) . ? C7 C1 1.474(9) . ? C7 C8 1.475(9) . ? C8 C9 1.403(10) . ? C9 C10 1.492(10) . ? C1 C2 1.379(10) . ? C11 C10 1.515(10) . ? C11 C16 1.562(10) . ? C17 C22 1.385(11) . ? C17 C18 1.418(11) . ? C17 C16 1.524(9) . ? C22 C21 1.410(10) . ? C22 C25 1.503(11) . ? C21 C20 1.371(12) . ? C19 C20 1.360(12) . ? C19 C18 1.398(11) . ? C18 C23 1.518(11) . ? C4 C5 1.373(10) . ? C4 C3 1.375(10) . ? C4 C6 1.498(10) . ? C3 C2 1.384(10) . ? C26 C25 1.527(11) . ? C24 C23 1.515(11) . ? C6 F1 1.334(10) . ? C6 F3 1.335(8) . ? C6 F2 1.342(10) . ? Cl3 C27 1.723(13) . ? Cl4 C27 1.765(12) . ?