# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'VICENTE, J.' _publ_contact_author_email jvs1@um.es _publ_section_title ; Quantitative Synthesis and Full Characterization of the First Isolated and Stable Pincer Palladium(IV) Complexes. Quantitative and Regioselective Synthesis of the C\^a X (X = Cl, Br) Reductive Elimination Products ; loop_ _publ_author_name VICENTE A.ARCAS F.JULIA-HERNANDEZ # Attachment '1b-fjf41s.cif' data_fjf41s _database_code_depnum_ccdc_archive 'CCDC 784548' #TrackingRef '1b-fjf41s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Br N O3 Pd' _chemical_formula_weight 394.54 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6687(7) _cell_length_b 9.9942(7) _cell_length_c 13.8064(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.748(2) _cell_angle_gamma 90.00 _cell_volume 1270.63(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9761 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.60 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.062 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 4.600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5684 _exptl_absorpt_correction_T_max 0.6562 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15327 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.67 _reflns_number_total 3089 _reflns_number_gt 2930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+1.2488P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3089 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0204 _refine_ls_R_factor_gt 0.0190 _refine_ls_wR_factor_ref 0.0459 _refine_ls_wR_factor_gt 0.0454 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.530440(15) 0.024079(14) 0.125715(11) 0.01223(5) Uani 1 1 d . . . N1 N 0.60175(18) 0.21073(16) 0.13309(12) 0.0138(3) Uani 1 1 d . . . Br1 Br 0.44642(2) -0.204083(19) 0.124329(15) 0.01738(6) Uani 1 1 d . . . O1 O 0.76467(15) 0.00180(14) 0.14230(12) 0.0192(3) Uani 1 1 d . . . C1 C 0.3428(2) 0.1097(2) 0.12383(17) 0.0202(4) Uani 1 1 d . . . H1A H 0.2610 0.0664 0.0720 0.024 Uiso 1 1 calc R . . H1B H 0.3269 0.0998 0.1910 0.024 Uiso 1 1 calc R . . C2 C 0.3510(2) 0.2555(2) 0.09897(15) 0.0181(4) Uani 1 1 d . . . O3 O 0.24482(17) 0.32597(16) 0.06368(14) 0.0294(4) Uani 1 1 d . . . C3 C 0.5012(2) 0.3085(2) 0.11789(14) 0.0150(4) Uani 1 1 d . . . C4 C 0.5385(2) 0.4414(2) 0.11645(15) 0.0184(4) Uani 1 1 d . . . H4 H 0.4671 0.5097 0.1060 0.022 Uiso 1 1 calc R . . C5 C 0.6830(3) 0.4728(2) 0.13072(17) 0.0227(4) Uani 1 1 d . . . H5 H 0.7123 0.5635 0.1308 0.027 Uiso 1 1 calc R . . C6 C 0.7847(2) 0.3708(2) 0.14491(17) 0.0224(4) Uani 1 1 d . . . H6 H 0.8838 0.3916 0.1542 0.027 Uiso 1 1 calc R . . C7 C 0.7414(2) 0.2385(2) 0.14545(15) 0.0174(4) Uani 1 1 d . . . C8 C 0.8500(2) 0.1222(2) 0.15919(16) 0.0195(4) Uani 1 1 d . . . O2 O 0.95183(15) 0.12287(16) 0.25632(11) 0.0219(3) Uani 1 1 d . . . C9 C 0.9369(2) 0.1328(2) 0.08370(17) 0.0246(4) Uani 1 1 d . . . H9A H 0.9949 0.2150 0.0969 0.037 Uiso 1 1 calc R . . H9B H 0.8700 0.1349 0.0142 0.037 Uiso 1 1 calc R . . H9C H 1.0015 0.0553 0.0916 0.037 Uiso 1 1 calc R . . C10 C 0.8904(3) 0.1197(2) 0.33898(17) 0.0251(4) Uani 1 1 d . . . H10A H 0.8322 0.2005 0.3371 0.038 Uiso 1 1 calc R . . H10B H 0.9687 0.1160 0.4037 0.038 Uiso 1 1 calc R . . H10C H 0.8285 0.0405 0.3325 0.038 Uiso 1 1 calc R . . C11 C 0.8426(2) -0.1230(2) 0.16299(19) 0.0267(5) Uani 1 1 d . . . H11A H 0.9357 -0.1135 0.1492 0.040 Uiso 1 1 calc R . . H11B H 0.7850 -0.1932 0.1194 0.040 Uiso 1 1 calc R . . H11C H 0.8600 -0.1472 0.2345 0.040 Uiso 1 1 calc R . . 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 0.01374(8) 0.00819(8) 0.01425(8) 0.00009(5) 0.00352(6) -0.00026(5) N1 0.0170(8) 0.0109(7) 0.0121(7) -0.0004(6) 0.0022(6) -0.0006(6) Br1 0.02466(11) 0.00997(9) 0.01763(10) 0.00009(7) 0.00662(8) -0.00353(7) O1 0.0134(7) 0.0113(6) 0.0310(8) -0.0011(6) 0.0038(6) 0.0009(5) C1 0.0172(9) 0.0153(9) 0.0300(11) 0.0013(8) 0.0098(8) 0.0011(7) C2 0.0207(10) 0.0159(9) 0.0192(10) -0.0007(8) 0.0081(8) 0.0031(8) O3 0.0201(8) 0.0218(8) 0.0446(10) 0.0051(7) 0.0072(7) 0.0073(6) C3 0.0203(10) 0.0135(9) 0.0109(8) -0.0008(7) 0.0044(7) 0.0022(7) C4 0.0263(10) 0.0129(9) 0.0144(9) 0.0002(7) 0.0038(8) 0.0054(8) C5 0.0328(12) 0.0105(9) 0.0214(10) 0.0008(8) 0.0034(9) -0.0052(8) C6 0.0202(10) 0.0170(10) 0.0264(11) -0.0006(8) 0.0017(8) -0.0059(8) C7 0.0174(9) 0.0139(9) 0.0185(9) -0.0004(7) 0.0016(7) -0.0016(7) C8 0.0165(9) 0.0153(9) 0.0242(10) -0.0012(8) 0.0025(8) -0.0016(7) O2 0.0171(7) 0.0227(8) 0.0234(8) -0.0026(6) 0.0024(6) 0.0005(6) C9 0.0223(10) 0.0276(12) 0.0260(11) -0.0026(9) 0.0105(9) 0.0010(9) C10 0.0284(11) 0.0238(11) 0.0228(11) 0.0004(9) 0.0073(9) 0.0006(9) C11 0.0212(10) 0.0148(10) 0.0399(13) 0.0003(9) 0.0027(9) 0.0058(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 1.9806(16) . ? Pd1 C1 1.999(2) . ? Pd1 O1 2.2169(14) . ? Pd1 Br1 2.4188(3) . ? N1 C7 1.337(3) . ? N1 C3 1.349(3) . ? O1 C8 1.438(2) . ? O1 C11 1.440(2) . ? C1 C2 1.504(3) . ? C2 O3 1.218(3) . ? C2 C3 1.492(3) . ? C3 C4 1.378(3) . ? C4 C5 1.387(3) . ? C5 C6 1.387(3) . ? C6 C7 1.388(3) . ? C7 C8 1.539(3) . ? C8 O2 1.401(2) . ? C8 C9 1.529(3) . ? O2 C10 1.439(3) . ? 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 N1 Pd1 C1 84.14(8) . . ? N1 Pd1 O1 76.15(6) . . ? C1 Pd1 O1 159.87(7) . . ? N1 Pd1 Br1 177.63(5) . . ? C1 Pd1 Br1 95.86(6) . . ? O1 Pd1 Br1 103.66(4) . . ? C7 N1 C3 121.42(17) . . ? C7 N1 Pd1 121.59(13) . . ? C3 N1 Pd1 116.83(14) . . ? C8 O1 C11 116.94(15) . . ? C8 O1 Pd1 116.79(11) . . ? C11 O1 Pd1 124.31(13) . . ? C2 C1 Pd1 107.85(13) . . ? O3 C2 C3 121.40(19) . . ? O3 C2 C1 123.71(19) . . ? C3 C2 C1 114.87(17) . . ? N1 C3 C4 121.43(19) . . ? N1 C3 C2 112.73(17) . . ? C4 C3 C2 125.79(19) . . ? C3 C4 C5 118.20(19) . . ? C4 C5 C6 119.60(19) . . ? C5 C6 C7 119.93(19) . . ? N1 C7 C6 119.40(19) . . ? N1 C7 C8 118.95(17) . . ? C6 C7 C8 121.64(18) . . ? O2 C8 O1 111.13(17) . . ? O2 C8 C9 106.31(17) . . ? O1 C8 C9 110.80(17) . . ? O2 C8 C7 111.62(17) . . ? O1 C8 C7 105.98(15) . . ? C9 C8 C7 111.10(18) . . ? C8 O2 C10 114.83(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 Br1 0.95 2.88 3.663(2) 140.0 1_565 _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.764 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.082 # Attachment '2a-fje221s.cif' data_fje221s _database_code_depnum_ccdc_archive 'CCDC 784549' #TrackingRef '2a-fje221s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cl3 N O3 Pd' _chemical_formula_weight 420.98 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 8.5235(4) _cell_length_b 13.5319(7) _cell_length_c 12.8239(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.407(2) _cell_angle_gamma 90.00 _cell_volume 1463.20(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5109 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.01 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7666 _exptl_absorpt_correction_T_max 0.8536 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16440 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.15 _reflns_number_total 3390 _reflns_number_gt 3196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The group [C(OMe)(Me)] is disordered over two positions ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+1.1838P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'ordered methyls rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3390 _refine_ls_number_parameters 190 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0198 _refine_ls_wR_factor_ref 0.0486 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 1.092502(15) 0.378873(10) 0.747840(10) 0.01418(5) Uani 1 1 d . A . Cl1 Cl 0.95948(5) 0.28403(3) 0.61380(4) 0.02019(10) Uani 1 1 d . . . Cl2 Cl 1.31557(5) 0.37325(4) 0.67009(4) 0.02278(10) Uani 1 1 d . . . Cl3 Cl 1.22123(5) 0.46968(4) 0.88589(4) 0.02357(10) Uani 1 1 d . . . N1 N 0.89681(18) 0.38364(11) 0.81762(12) 0.0148(3) Uani 1 1 d . A . O1 O 0.96246(14) 0.51815(9) 0.68444(10) 0.0166(3) Uani 1 1 d . . . C1 C 1.1468(2) 0.25497(14) 0.83407(15) 0.0219(4) Uani 1 1 d . . . H1A H 1.1422 0.1964 0.7875 0.026 Uiso 1 1 calc R A . H1B H 1.2550 0.2600 0.8741 0.026 Uiso 1 1 calc R . . C2 C 1.0253(2) 0.24618(13) 0.90877(14) 0.0181(4) Uani 1 1 d . A . O2 O 1.04337(17) 0.18615(11) 0.97861(11) 0.0277(3) Uani 1 1 d . . . C3 C 0.8863(2) 0.31466(13) 0.89169(13) 0.0155(3) Uani 1 1 d . . . C4 C 0.7586(2) 0.31129(14) 0.94589(14) 0.0186(4) Uani 1 1 d . A . H4 H 0.7523 0.2628 0.9987 0.022 Uiso 1 1 calc R . . C5 C 0.6388(2) 0.38100(14) 0.92104(15) 0.0190(4) Uani 1 1 d . . . H5 H 0.5479 0.3798 0.9560 0.023 Uiso 1 1 calc R A . C6 C 0.6527(2) 0.45225(14) 0.84500(15) 0.0197(4) Uani 1 1 d . A . H6 H 0.5719 0.5004 0.8282 0.024 Uiso 1 1 calc R . . C7 C 0.7855(2) 0.45274(14) 0.79354(14) 0.0180(4) Uani 1 1 d . . . C8 C 0.8012(2) 0.52634(16) 0.70354(17) 0.0159(5) Uani 0.859(4) 1 d PD A 1 O3 O 0.77132(18) 0.62201(10) 0.73533(12) 0.0189(4) Uani 0.859(4) 1 d PD A 1 C9 C 0.8732(7) 0.6552(5) 0.8277(5) 0.0231(12) Uani 0.859(4) 1 d PD A 1 H9A H 0.8441 0.7228 0.8446 0.035 Uiso 0.859(4) 1 calc PR A 1 H9B H 0.9836 0.6541 0.8145 0.035 Uiso 0.859(4) 1 calc PR A 1 H9C H 0.8615 0.6115 0.8870 0.035 Uiso 0.859(4) 1 calc PR A 1 C10 C 0.6826(5) 0.5032(3) 0.6056(3) 0.0196(7) Uani 0.859(4) 1 d PD A 1 H10A H 0.7010 0.4360 0.5815 0.029 Uiso 0.859(4) 1 calc PR A 1 H10B H 0.6960 0.5505 0.5498 0.029 Uiso 0.859(4) 1 calc PR A 1 H10C H 0.5745 0.5081 0.6228 0.029 Uiso 0.859(4) 1 calc PR A 1 C8' C 0.8341(13) 0.5557(10) 0.7479(10) 0.012(3) Uiso 0.141(4) 1 d PD A 2 O3' O 0.7035(9) 0.5799(6) 0.6764(6) 0.011(2) Uiso 0.141(4) 1 d PD A 2 C9' C 0.644(2) 0.5039(16) 0.6057(18) 0.012(5) Uiso 0.141(4) 1 d PD A 2 H9'1 H 0.5527 0.5289 0.5572 0.018 Uiso 0.141(4) 1 calc PR A 2 H9'2 H 0.6099 0.4479 0.6456 0.018 Uiso 0.141(4) 1 calc PR A 2 H9'3 H 0.7266 0.4822 0.5654 0.018 Uiso 0.141(4) 1 calc PR A 2 C10' C 0.882(5) 0.642(3) 0.823(3) 0.030(11) Uiso 0.141(4) 1 d PD A 2 H10D H 0.9752 0.6229 0.8732 0.044 Uiso 0.141(4) 1 calc PR A 2 H10E H 0.7942 0.6583 0.8610 0.044 Uiso 0.141(4) 1 calc PR A 2 H10F H 0.9082 0.6993 0.7822 0.044 Uiso 0.141(4) 1 calc PR A 2 C11 C 1.0091(3) 0.58624(16) 0.60838(18) 0.0292(5) Uani 1 1 d . A . H11A H 0.9401 0.5776 0.5408 0.044 Uiso 1 1 calc R . . H11B H 1.1193 0.5734 0.5991 0.044 Uiso 1 1 calc R . . H11C H 0.9994 0.6541 0.6334 0.044 Uiso 1 1 calc R . . 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 0.01236(8) 0.01556(8) 0.01518(8) 0.00037(5) 0.00391(5) 0.00088(5) Cl1 0.0202(2) 0.0205(2) 0.0202(2) -0.00194(16) 0.00402(16) -0.00436(17) Cl2 0.0150(2) 0.0306(3) 0.0244(2) -0.00623(18) 0.00826(17) -0.00206(17) Cl3 0.0189(2) 0.0297(2) 0.0216(2) -0.00781(18) 0.00085(16) 0.00154(18) N1 0.0148(7) 0.0153(7) 0.0148(7) 0.0006(5) 0.0040(6) -0.0003(5) O1 0.0160(6) 0.0149(6) 0.0200(6) 0.0045(5) 0.0059(5) -0.0004(5) C1 0.0226(9) 0.0198(9) 0.0235(10) 0.0056(7) 0.0043(7) 0.0083(7) C2 0.0194(9) 0.0158(8) 0.0178(9) 0.0002(7) -0.0018(7) -0.0023(7) O2 0.0269(7) 0.0273(8) 0.0279(8) 0.0116(6) 0.0000(6) 0.0012(6) C3 0.0182(8) 0.0146(8) 0.0132(8) -0.0015(6) 0.0003(6) -0.0027(7) C4 0.0222(9) 0.0213(9) 0.0125(8) -0.0006(7) 0.0031(7) -0.0063(7) C5 0.0166(9) 0.0241(10) 0.0173(9) -0.0034(7) 0.0061(7) -0.0050(7) C6 0.0161(8) 0.0209(9) 0.0226(9) -0.0015(7) 0.0045(7) 0.0021(7) C7 0.0165(8) 0.0169(9) 0.0210(9) 0.0024(7) 0.0045(7) 0.0007(7) C8 0.0151(10) 0.0141(10) 0.0191(11) 0.0001(9) 0.0044(8) -0.0001(8) O3 0.0197(8) 0.0150(8) 0.0214(8) -0.0018(6) 0.0009(6) 0.0018(6) C9 0.0210(18) 0.022(2) 0.0254(19) -0.0074(14) 0.0001(11) 0.0001(14) C10 0.0168(17) 0.0231(14) 0.0188(14) -0.0001(8) 0.0021(13) -0.0024(13) C11 0.0270(10) 0.0268(11) 0.0360(12) 0.0151(9) 0.0124(9) -0.0015(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 2.0058(15) . ? Pd1 C1 2.0245(18) . ? Pd1 Cl2 2.2736(5) . ? Pd1 O1 2.2755(12) . ? Pd1 Cl3 2.2978(5) . ? Pd1 Cl1 2.3060(5) . ? N1 C7 1.336(2) . ? N1 C3 1.344(2) . ? O1 C8 1.436(2) . ? O1 C11 1.439(2) . ? O1 C8' 1.542(13) . ? C1 C2 1.515(3) . ? C2 O2 1.202(2) . ? C2 C3 1.494(2) . ? C3 C4 1.376(3) . ? C4 C5 1.392(3) . ? C5 C6 1.389(3) . ? C6 C7 1.391(3) . ? C7 C8 1.545(3) . ? C7 C8' 1.589(13) . ? C8 O3 1.392(3) . ? C8 C10 1.525(4) . ? O3 C9 1.435(5) . ? C8' O3' 1.374(12) . ? C8' C10' 1.527(18) . ? O3' C9' 1.417(16) . ? 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 N1 Pd1 C1 85.50(7) . . ? N1 Pd1 Cl2 179.52(4) . . ? C1 Pd1 Cl2 94.17(6) . . ? N1 Pd1 O1 74.89(5) . . ? C1 Pd1 O1 160.32(6) . . ? Cl2 Pd1 O1 105.42(3) . . ? N1 Pd1 Cl3 88.49(4) . . ? C1 Pd1 Cl3 88.67(6) . . ? Cl2 Pd1 Cl3 91.149(17) . . ? O1 Pd1 Cl3 89.15(3) . . ? N1 Pd1 Cl1 90.01(4) . . ? C1 Pd1 Cl1 89.68(6) . . ? Cl2 Pd1 Cl1 90.344(17) . . ? O1 Pd1 Cl1 91.94(3) . . ? Cl3 Pd1 Cl1 177.852(18) . . ? C7 N1 C3 122.09(16) . . ? C7 N1 Pd1 121.89(12) . . ? C3 N1 Pd1 116.01(12) . . ? C8 O1 C11 115.61(14) . . ? C8 O1 C8' 27.5(4) . . ? C11 O1 C8' 115.7(5) . . ? C8 O1 Pd1 115.57(11) . . ? C11 O1 Pd1 127.16(11) . . ? C8' O1 Pd1 115.5(4) . . ? C2 C1 Pd1 106.71(12) . . ? O2 C2 C3 122.74(17) . . ? O2 C2 C1 119.93(17) . . ? C3 C2 C1 117.33(15) . . ? N1 C3 C4 121.30(17) . . ? N1 C3 C2 113.65(15) . . ? C4 C3 C2 125.04(16) . . ? C3 C4 C5 118.03(17) . . ? C6 C5 C4 119.75(17) . . ? C5 C6 C7 119.69(17) . . ? N1 C7 C6 119.13(16) . . ? N1 C7 C8 119.20(16) . . ? C6 C7 C8 121.51(16) . . ? N1 C7 C8' 119.0(4) . . ? C6 C7 C8' 116.9(5) . . ? C8 C7 C8' 26.4(4) . . ? O3 C8 O1 110.02(16) . . ? O3 C8 C10 107.7(2) . . ? O1 C8 C10 112.3(2) . . ? O3 C8 C7 109.96(17) . . ? O1 C8 C7 105.50(15) . . ? C10 C8 C7 111.3(2) . . ? C8 O3 C9 114.8(3) . . ? O3' C8' C10' 110.7(18) . . ? O3' C8' O1 107.1(9) . . ? C10' C8' O1 116(2) . . ? O3' C8' C7 103.1(8) . . ? C10' C8' C7 120(2) . . ? O1 C8' C7 98.6(7) . . ? C8' O3' C9' 115.8(12) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10A O2 0.98 2.40 3.172(3) 135.2 4_565 _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.422 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.087 # Attachment '2b-fjf101s.cif' data_fjf101s _database_code_depnum_ccdc_archive 'CCDC 784550' #TrackingRef '2b-fjf101s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Br3 N O3 Pd' _chemical_formula_weight 554.36 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 8.8728(8) _cell_length_b 13.3587(12) _cell_length_c 13.1184(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.193(2) _cell_angle_gamma 90.00 _cell_volume 1534.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6006 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 28.48 _exptl_crystal_description block _exptl_crystal_colour dark_red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 9.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2119 _exptl_absorpt_correction_T_max 0.3263 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18602 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.72 _reflns_number_total 3734 _reflns_number_gt 3501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SAINT' _computing_publication_material 'Bruker SAINT' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The group [C(OMe)(Me)] is disordered over two positions. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0203P)^2^+0.8963P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'ordered methyls rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3734 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0184 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0402 _refine_ls_wR_factor_gt 0.0396 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd -0.090847(15) 0.126526(10) 0.249226(10) 0.01245(4) Uani 1 1 d . A . O1 O 0.03390(14) -0.01431(9) 0.31554(10) 0.0149(3) Uani 1 1 d . . . Br1 Br -0.22365(2) 0.028311(16) 0.105892(15) 0.02293(5) Uani 1 1 d . . . Br2 Br -0.31952(2) 0.134467(16) 0.325607(15) 0.02072(5) Uani 1 1 d . . . Br3 Br 0.04347(2) 0.229958(14) 0.389909(14) 0.01779(5) Uani 1 1 d . . . C1 C -0.1383(2) 0.25141(15) 0.16154(15) 0.0200(4) Uani 1 1 d . . . H1A H -0.2420 0.2469 0.1206 0.024 Uiso 1 1 calc R A . H1B H -0.1334 0.3116 0.2060 0.024 Uiso 1 1 calc R . . C2 C -0.0193(2) 0.25745(14) 0.09070(14) 0.0164(4) Uani 1 1 d . A . O2 O -0.03507(17) 0.31588(12) 0.02022(12) 0.0278(3) Uani 1 1 d . . . C3 C 0.1140(2) 0.18797(13) 0.11139(13) 0.0138(3) Uani 1 1 d . . . N1 N 0.10059(18) 0.11893(11) 0.18430(12) 0.0135(3) Uani 1 1 d . A . C4 C 0.2396(2) 0.19060(14) 0.06224(14) 0.0166(4) Uani 1 1 d . A . H4 H 0.2485 0.2395 0.0109 0.020 Uiso 1 1 calc R . . C5 C 0.3536(2) 0.11948(14) 0.08995(14) 0.0166(4) Uani 1 1 d . . . H5 H 0.4431 0.1205 0.0588 0.020 Uiso 1 1 calc R A . C6 C 0.3364(2) 0.04737(14) 0.16275(14) 0.0170(4) Uani 1 1 d . A . H6 H 0.4125 -0.0024 0.1805 0.020 Uiso 1 1 calc R . . C7 C 0.2059(2) 0.04845(14) 0.21009(15) 0.0174(4) Uani 1 1 d . . . C8 C 0.1896(3) -0.0240(2) 0.2994(2) 0.0143(6) Uani 0.748(4) 1 d P A 1 C10 C 0.3036(6) -0.0003(4) 0.3972(4) 0.0182(9) Uani 0.748(4) 1 d P A 1 H10A H 0.2867 0.0681 0.4198 0.027 Uiso 0.748(4) 1 calc PR A 1 H10B H 0.4080 -0.0064 0.3822 0.027 Uiso 0.748(4) 1 calc PR A 1 H10C H 0.2891 -0.0475 0.4519 0.027 Uiso 0.748(4) 1 calc PR A 1 O3 O 0.2172(2) -0.12152(13) 0.26948(14) 0.0171(5) Uani 0.748(4) 1 d P A 1 C9 C 0.1225(8) -0.1547(5) 0.1795(6) 0.0212(13) Uani 0.748(4) 1 d P A 1 H9A H 0.1496 -0.2237 0.1644 0.032 Uiso 0.748(4) 1 calc PR A 1 H9B H 0.1363 -0.1114 0.1215 0.032 Uiso 0.748(4) 1 calc PR A 1 H9C H 0.0157 -0.1523 0.1900 0.032 Uiso 0.748(4) 1 calc PR A 1 C8' C 0.1594(10) -0.0512(7) 0.2593(7) 0.0148(18) Uiso 0.252(4) 1 d P A 2 C9' C 0.3414(15) -0.0016(13) 0.4018(13) 0.017(4) Uiso 0.252(4) 1 d P A 2 H9'1 H 0.4268 -0.0280 0.4511 0.025 Uiso 0.252(4) 1 calc PR A 2 H9'2 H 0.2613 0.0225 0.4392 0.025 Uiso 0.252(4) 1 calc PR A 2 H9'3 H 0.3773 0.0539 0.3630 0.025 Uiso 0.252(4) 1 calc PR A 2 O3' O 0.2821(6) -0.0780(4) 0.3327(4) 0.0149(15) Uiso 0.252(4) 1 d P A 2 C10' C 0.107(3) -0.1415(17) 0.182(2) 0.020(5) Uiso 0.252(4) 1 d P A 2 H10D H 0.0203 -0.1203 0.1311 0.031 Uiso 0.252(4) 1 calc PR A 2 H10E H 0.0765 -0.1985 0.2216 0.031 Uiso 0.252(4) 1 calc PR A 2 H10F H 0.1919 -0.1614 0.1474 0.031 Uiso 0.252(4) 1 calc PR A 2 C11 C -0.0153(3) -0.08405(17) 0.38702(19) 0.0307(5) Uani 1 1 d . A . H11A H -0.0111 -0.1522 0.3600 0.046 Uiso 1 1 calc R . . H11B H -0.1203 -0.0684 0.3960 0.046 Uiso 1 1 calc R . . H11C H 0.0520 -0.0790 0.4538 0.046 Uiso 1 1 calc R . . 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 0.01052(7) 0.01444(7) 0.01297(7) -0.00007(5) 0.00365(5) 0.00131(5) O1 0.0148(6) 0.0137(6) 0.0176(6) 0.0045(5) 0.0073(5) -0.0004(5) Br1 0.01886(10) 0.02847(11) 0.02059(10) -0.01006(8) 0.00052(7) 0.00246(8) Br2 0.01236(9) 0.02924(11) 0.02210(10) -0.00787(8) 0.00740(7) -0.00180(7) Br3 0.01675(9) 0.01947(10) 0.01737(9) -0.00119(7) 0.00341(7) -0.00444(7) C1 0.0215(10) 0.0189(9) 0.0192(9) 0.0039(7) 0.0024(7) 0.0087(8) C2 0.0174(9) 0.0142(9) 0.0161(8) 0.0001(7) -0.0020(7) -0.0012(7) O2 0.0265(8) 0.0269(8) 0.0293(8) 0.0142(6) 0.0023(6) 0.0030(6) C3 0.0172(9) 0.0123(8) 0.0112(8) -0.0003(6) 0.0004(7) -0.0013(7) N1 0.0142(7) 0.0129(7) 0.0140(7) 0.0018(6) 0.0045(6) 0.0010(6) C4 0.0211(9) 0.0167(9) 0.0122(8) 0.0003(7) 0.0034(7) -0.0053(7) C5 0.0139(8) 0.0209(9) 0.0164(9) -0.0037(7) 0.0064(7) -0.0041(7) C6 0.0144(8) 0.0160(9) 0.0213(9) 0.0002(7) 0.0051(7) 0.0011(7) C7 0.0151(9) 0.0156(9) 0.0227(9) 0.0051(7) 0.0067(7) 0.0021(7) C8 0.0137(12) 0.0120(12) 0.0182(13) 0.0016(11) 0.0057(10) 0.0012(9) C10 0.016(2) 0.0196(17) 0.0184(17) 0.0016(10) 0.0021(17) 0.0003(17) O3 0.0186(10) 0.0119(9) 0.0203(10) -0.0001(7) 0.0017(7) 0.0007(7) C9 0.017(2) 0.017(2) 0.029(2) -0.0021(18) 0.0022(15) 0.0025(17) C11 0.0303(11) 0.0254(11) 0.0408(13) 0.0150(10) 0.0191(10) -0.0001(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 2.0207(15) . ? Pd1 C1 2.0319(19) . ? Pd1 O1 2.2833(13) . ? Pd1 Br2 2.4045(3) . ? Pd1 Br1 2.4367(3) . ? Pd1 Br3 2.4561(3) . ? O1 C8 1.436(3) . ? O1 C11 1.438(2) . ? O1 C8' 1.513(8) . ? C1 C2 1.517(3) . ? C2 O2 1.201(2) . ? C2 C3 1.493(3) . ? C3 N1 1.347(2) . ? C3 C4 1.375(3) . ? N1 C7 1.331(2) . ? C4 C5 1.393(3) . ? C5 C6 1.382(3) . ? C6 C7 1.399(2) . ? C7 C8 1.545(3) . ? C7 C8' 1.563(8) . ? C8 O3 1.393(3) . ? C8 C10 1.534(6) . ? O3 C9 1.407(8) . ? C8' O3' 1.380(10) . ? C8' C10' 1.59(3) . ? C9' O3' 1.410(17) . ? 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 N1 Pd1 C1 85.12(7) . . ? N1 Pd1 O1 74.35(5) . . ? C1 Pd1 O1 159.42(6) . . ? N1 Pd1 Br2 179.53(5) . . ? C1 Pd1 Br2 95.00(6) . . ? O1 Pd1 Br2 105.52(3) . . ? N1 Pd1 Br1 89.03(4) . . ? C1 Pd1 Br1 88.52(6) . . ? O1 Pd1 Br1 89.75(3) . . ? Br2 Pd1 Br1 90.521(10) . . ? N1 Pd1 Br3 90.31(4) . . ? C1 Pd1 Br3 89.73(6) . . ? O1 Pd1 Br3 91.71(3) . . ? Br2 Pd1 Br3 90.143(9) . . ? Br1 Pd1 Br3 178.184(9) . . ? C8 O1 C11 115.88(16) . . ? C8 O1 C8' 25.7(3) . . ? C11 O1 C8' 115.5(3) . . ? C8 O1 Pd1 115.95(12) . . ? C11 O1 Pd1 127.09(12) . . ? C8' O1 Pd1 115.6(3) . . ? C2 C1 Pd1 106.79(12) . . ? O2 C2 C3 122.39(18) . . ? O2 C2 C1 119.95(18) . . ? C3 C2 C1 117.66(16) . . ? N1 C3 C4 121.36(17) . . ? N1 C3 C2 113.42(15) . . ? C4 C3 C2 125.21(17) . . ? C7 N1 C3 121.78(16) . . ? C7 N1 Pd1 122.09(12) . . ? C3 N1 Pd1 116.11(12) . . ? C3 C4 C5 118.00(17) . . ? C6 C5 C4 120.03(17) . . ? C5 C6 C7 119.33(17) . . ? N1 C7 C6 119.44(17) . . ? N1 C7 C8 119.30(16) . . ? C6 C7 C8 120.97(17) . . ? N1 C7 C8' 119.1(3) . . ? C6 C7 C8' 117.8(3) . . ? C8 C7 C8' 24.5(3) . . ? O3 C8 O1 110.1(2) . . ? O3 C8 C10 107.8(3) . . ? O1 C8 C10 112.3(3) . . ? O3 C8 C7 109.3(2) . . ? O1 C8 C7 105.29(17) . . ? C10 C8 C7 112.0(3) . . ? C8 O3 C9 115.0(3) . . ? O3' C8' O1 107.7(6) . . ? O3' C8' C7 106.2(6) . . ? O1 C8' C7 100.8(5) . . ? O3' C8' C10' 111.2(10) . . ? O1 C8' C10' 113.1(10) . . ? C7 C8' C10' 117.0(11) . . ? C8' O3' C9' 115.6(8) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.434 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.089