# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 885700' #TrackingRef 'Complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Br Cl2 N2 Pd S' _chemical_formula_sum 'C11 H11 Br Cl2 N2 Pd S' _chemical_formula_weight 460.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.521(8) _cell_length_b 8.197(4) _cell_length_c 10.474(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.026(9) _cell_angle_gamma 90.00 _cell_volume 1410.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5603 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 23.67 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 2.168 _exptl_crystal_density_diffrn 2.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888.0 _exptl_absorpt_coefficient_mu 4.656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.240 _exptl_absorpt_correction_T_max 0.379 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10936 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2486 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0382P)^2^+0.4574P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2356 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Br1 Br 0.52416(2) 0.60765(5) 0.26618(4) 0.05393(14) Uani 1 1 d . . . C1 C 0.0791(2) 0.7808(4) 0.5484(3) 0.0470(8) Uani 1 1 d . . . H1 H 0.1087 0.8485 0.4993 0.056 Uiso 1 1 calc R . . C2 C -0.0042(2) 0.7703(5) 0.5229(4) 0.0596(10) Uani 1 1 d . . . H2 H -0.0310 0.8324 0.4573 0.072 Uiso 1 1 calc R . . C3 C -0.0474(2) 0.6697(6) 0.5931(5) 0.0664(11) Uani 1 1 d . . . H3 H -0.1037 0.6644 0.5766 0.080 Uiso 1 1 calc R . . C4 C -0.0080(3) 0.5761(5) 0.6883(5) 0.0694(12) Uani 1 1 d . . . H4 H -0.0377 0.5047 0.7343 0.083 Uiso 1 1 calc R . . C5 C 0.0744(3) 0.5864(4) 0.7164(4) 0.0553(10) Uani 1 1 d . . . H5 H 0.1008 0.5235 0.7821 0.066 Uiso 1 1 calc R . . C6 C 0.11808(18) 0.6907(4) 0.6469(3) 0.0370(7) Uani 1 1 d . . . C7 C 0.2562(2) 0.5110(4) 0.6393(3) 0.0465(8) Uani 1 1 d . . . H7A H 0.3107 0.4879 0.6793 0.056 Uiso 1 1 calc R . . H7B H 0.2202 0.4276 0.6667 0.056 Uiso 1 1 calc R . . C8 C 0.25617(19) 0.5019(4) 0.4951(3) 0.0419(7) Uani 1 1 d . . . H8A H 0.2544 0.3885 0.4685 0.050 Uiso 1 1 calc R . . H8B H 0.2078 0.5554 0.4544 0.050 Uiso 1 1 calc R . . C9 C 0.37998(18) 0.5125(4) 0.3807(3) 0.0405(7) Uani 1 1 d . . . H9 H 0.3777 0.4077 0.3465 0.049 Uiso 1 1 calc R . . C10 C 0.43731(19) 0.6262(4) 0.3660(3) 0.0384(7) Uani 1 1 d . . . C11 C 0.41775(18) 0.7609(4) 0.4333(3) 0.0392(7) Uani 1 1 d . . . H11 H 0.4475 0.8573 0.4407 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.20446(5) 1.08372(10) 0.66707(9) 0.0476(2) Uani 1 1 d . . . Cl2 Cl 0.33658(7) 1.10138(9) 0.46145(11) 0.0610(3) Uani 1 1 d . . . N1 N 0.32742(15) 0.5783(3) 0.4532(3) 0.0365(6) Uani 1 1 d . . . N2 N 0.34923(15) 0.7324(3) 0.4866(2) 0.0347(5) Uani 1 1 d . . . Pd1 Pd 0.280380(13) 0.89639(2) 0.57200(2) 0.03174(11) Uani 1 1 d . . . S1 S 0.22449(5) 0.70630(10) 0.69421(7) 0.03716(19) Uani 1 1 d . . . 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 Br1 0.0402(2) 0.0586(3) 0.0666(3) -0.00512(17) 0.02246(18) 0.00462(15) C1 0.0376(18) 0.047(2) 0.057(2) 0.0029(16) 0.0060(15) -0.0032(15) C2 0.0388(19) 0.059(2) 0.079(3) -0.008(2) -0.0004(18) -0.0013(18) C3 0.037(2) 0.072(3) 0.092(3) -0.023(3) 0.015(2) -0.013(2) C4 0.057(3) 0.072(3) 0.085(3) -0.010(2) 0.036(2) -0.027(2) C5 0.058(2) 0.055(2) 0.056(2) 0.0039(17) 0.0206(18) -0.0087(17) C6 0.0338(16) 0.0368(17) 0.0426(17) -0.0050(14) 0.0139(13) -0.0028(13) C7 0.0434(18) 0.0316(17) 0.066(2) 0.0130(16) 0.0145(16) 0.0054(14) C8 0.0349(16) 0.0256(15) 0.067(2) -0.0042(15) 0.0133(15) -0.0015(13) C9 0.0360(17) 0.0330(17) 0.0536(19) -0.0050(14) 0.0105(14) 0.0073(14) C10 0.0289(16) 0.0412(18) 0.0461(18) 0.0002(14) 0.0082(13) 0.0055(13) C11 0.0350(16) 0.0362(17) 0.0477(18) -0.0006(15) 0.0102(14) -0.0065(13) Cl1 0.0458(5) 0.0364(4) 0.0629(5) -0.0066(4) 0.0170(4) 0.0054(3) Cl2 0.0793(7) 0.0309(5) 0.0799(7) 0.0048(4) 0.0412(6) -0.0023(4) N1 0.0317(14) 0.0248(13) 0.0541(16) -0.0025(11) 0.0097(12) 0.0014(10) N2 0.0319(13) 0.0272(12) 0.0459(14) -0.0040(11) 0.0086(11) -0.0025(11) Pd1 0.03028(16) 0.02577(16) 0.03992(17) -0.00091(9) 0.00721(10) -0.00047(8) S1 0.0370(4) 0.0367(4) 0.0381(4) 0.0039(3) 0.0049(3) -0.0013(3) _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 Br1 C10 1.868(3) . ? C1 C6 1.373(5) . ? C1 C2 1.377(5) . ? C1 H1 0.9300 . ? C2 C3 1.356(6) . ? C2 H2 0.9300 . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 C5 1.365(6) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C5 H5 0.9300 . ? C6 S1 1.780(3) . ? C7 C8 1.513(5) . ? C7 S1 1.797(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.442(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.327(4) . ? C9 C10 1.349(4) . ? C9 H9 0.9300 . ? C10 C11 1.367(4) . ? C11 N2 1.335(4) . ? C11 H11 0.9300 . ? Cl1 Pd1 2.2770(11) . ? Cl2 Pd1 2.2917(11) . ? N1 N2 1.350(3) . ? N2 Pd1 2.028(2) . ? Pd1 S1 2.2731(11) . ? 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 C6 C1 C2 119.5(4) . . ? C6 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.4(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.1(3) . . ? C1 C6 S1 122.8(3) . . ? C5 C6 S1 117.1(3) . . ? C8 C7 S1 113.2(2) . . ? C8 C7 H7A 108.9 . . ? S1 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? S1 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C7 111.6(3) . . ? N1 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C10 107.1(3) . . ? N1 C9 H9 126.5 . . ? C10 C9 H9 126.5 . . ? C9 C10 C11 107.0(3) . . ? C9 C10 Br1 126.7(2) . . ? C11 C10 Br1 126.3(2) . . ? N2 C11 C10 109.4(3) . . ? N2 C11 H11 125.3 . . ? C10 C11 H11 125.3 . . ? C9 N1 N2 110.9(2) . . ? C9 N1 C8 127.0(3) . . ? N2 N1 C8 122.1(2) . . ? C11 N2 N1 105.6(2) . . ? C11 N2 Pd1 127.5(2) . . ? N1 N2 Pd1 126.01(19) . . ? N2 Pd1 S1 94.23(8) . . ? N2 Pd1 Cl1 179.08(7) . . ? S1 Pd1 Cl1 86.62(5) . . ? N2 Pd1 Cl2 89.28(8) . . ? S1 Pd1 Cl2 175.70(3) . . ? Cl1 Pd1 Cl2 89.86(5) . . ? C6 S1 C7 99.19(15) . . ? C6 S1 Pd1 109.89(11) . . ? C7 S1 Pd1 106.32(12) . . ? 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 C6 C1 C2 C3 -1.0(6) . . . . ? C1 C2 C3 C4 -1.1(6) . . . . ? C2 C3 C4 C5 2.1(7) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C2 C1 C6 C5 2.3(5) . . . . ? C2 C1 C6 S1 -175.6(3) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? C4 C5 C6 S1 176.7(3) . . . . ? S1 C7 C8 N1 79.2(3) . . . . ? N1 C9 C10 C11 0.8(4) . . . . ? N1 C9 C10 Br1 -176.5(2) . . . . ? C9 C10 C11 N2 -1.0(4) . . . . ? Br1 C10 C11 N2 176.3(2) . . . . ? C10 C9 N1 N2 -0.2(3) . . . . ? C10 C9 N1 C8 -179.5(3) . . . . ? C7 C8 N1 C9 126.2(3) . . . . ? C7 C8 N1 N2 -53.0(4) . . . . ? C10 C11 N2 N1 0.9(3) . . . . ? C10 C11 N2 Pd1 -169.0(2) . . . . ? C9 N1 N2 C11 -0.4(3) . . . . ? C8 N1 N2 C11 178.9(3) . . . . ? C9 N1 N2 Pd1 169.6(2) . . . . ? C8 N1 N2 Pd1 -11.0(4) . . . . ? C11 N2 Pd1 S1 -156.0(2) . . . . ? N1 N2 Pd1 S1 36.1(2) . . . . ? C11 N2 Pd1 Cl2 21.5(3) . . . . ? N1 N2 Pd1 Cl2 -146.4(2) . . . . ? C1 C6 S1 C7 -109.9(3) . . . . ? C5 C6 S1 C7 72.1(3) . . . . ? C1 C6 S1 Pd1 1.3(3) . . . . ? C5 C6 S1 Pd1 -176.7(2) . . . . ? C8 C7 S1 C6 74.6(3) . . . . ? C8 C7 S1 Pd1 -39.4(3) . . . . ? N2 Pd1 S1 C6 -114.41(13) . . . . ? Cl1 Pd1 S1 C6 65.93(11) . . . . ? N2 Pd1 S1 C7 -7.98(14) . . . . ? Cl1 Pd1 S1 C7 172.36(12) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.488 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.090 data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 885701' #TrackingRef 'Complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Br Cl2 N2 Pd Se' _chemical_formula_sum 'C11 H11 Br Cl2 N2 Pd Se' _chemical_formula_weight 507.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.787(6) _cell_length_b 8.256(3) _cell_length_c 10.585(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.366(6) _cell_angle_gamma 90.00 _cell_volume 1460.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4376 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 23.62 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 2.307 _exptl_crystal_density_diffrn 2.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960.0 _exptl_absorpt_coefficient_mu 6.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.137 _exptl_absorpt_correction_T_max 0.225 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12585 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2549 _reflns_number_gt 2191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0330P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2549 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0638 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Br1 Br 0.52465(3) 0.09895(6) 0.26781(5) 0.05462(15) Uani 1 1 d . . . C1 C 0.0778(2) 0.2785(5) 0.5518(4) 0.0450(10) Uani 1 1 d . . . H1 H 0.1086 0.3458 0.5055 0.054 Uiso 1 1 calc R . . C2 C -0.0043(3) 0.2708(6) 0.5226(5) 0.0591(13) Uani 1 1 d . . . H2 H -0.0287 0.3338 0.4572 0.071 Uiso 1 1 calc R . . C3 C -0.0494(3) 0.1704(7) 0.5902(6) 0.0695(16) Uani 1 1 d . . . H3 H -0.1046 0.1665 0.5718 0.083 Uiso 1 1 calc R . . C4 C -0.0132(3) 0.0759(7) 0.6847(6) 0.0703(16) Uani 1 1 d . . . H4 H -0.0440 0.0059 0.7289 0.084 Uiso 1 1 calc R . . C5 C 0.0681(3) 0.0830(6) 0.7154(4) 0.0533(12) Uani 1 1 d . . . H5 H 0.0924 0.0187 0.7801 0.064 Uiso 1 1 calc R . . C6 C 0.1133(2) 0.1870(4) 0.6486(4) 0.0374(9) Uani 1 1 d . . . C7 C 0.2550(2) -0.0084(4) 0.6343(4) 0.0415(10) Uani 1 1 d . . . H7A H 0.3074 -0.0400 0.6724 0.050 Uiso 1 1 calc R . . H7B H 0.2170 -0.0897 0.6565 0.050 Uiso 1 1 calc R . . C8 C 0.2561(2) -0.0046(4) 0.4913(4) 0.0392(10) Uani 1 1 d . . . H8A H 0.2526 -0.1145 0.4588 0.047 Uiso 1 1 calc R . . H8B H 0.2096 0.0543 0.4543 0.047 Uiso 1 1 calc R . . C9 C 0.3806(2) 0.0060(5) 0.3795(4) 0.0400(10) Uani 1 1 d . . . H9 H 0.3779 -0.0971 0.3440 0.048 Uiso 1 1 calc R . . C10 C 0.4389(2) 0.1187(5) 0.3667(4) 0.0362(9) Uani 1 1 d . . . C11 C 0.4193(2) 0.2522(5) 0.4359(4) 0.0387(10) Uani 1 1 d . . . H11 H 0.4494 0.3467 0.4454 0.046 Uiso 1 1 calc R . . Cl1 Cl 0.20628(6) 0.57744(12) 0.66476(11) 0.0472(3) Uani 1 1 d . . . Cl2 Cl 0.33663(8) 0.59511(12) 0.45476(12) 0.0594(3) Uani 1 1 d . . . N1 N 0.32814(18) 0.0716(3) 0.4528(3) 0.0348(8) Uani 1 1 d . . . N2 N 0.35043(18) 0.2255(4) 0.4874(3) 0.0346(7) Uani 1 1 d . . . Pd1 Pd 0.282676(17) 0.39155(3) 0.57075(3) 0.03097(11) Uani 1 1 d . . . Se1 Se 0.22628(2) 0.19917(5) 0.70429(4) 0.03615(13) Uani 1 1 d . . . 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 Br1 0.0404(3) 0.0582(3) 0.0688(3) -0.0059(2) 0.0234(2) 0.0038(2) C1 0.035(2) 0.041(2) 0.059(3) 0.003(2) 0.004(2) -0.0057(19) C2 0.043(3) 0.057(3) 0.075(3) -0.006(3) -0.005(2) -0.005(2) C3 0.036(3) 0.080(4) 0.094(4) -0.033(3) 0.010(3) -0.011(3) C4 0.055(3) 0.083(4) 0.077(4) -0.011(3) 0.030(3) -0.029(3) C5 0.053(3) 0.059(3) 0.051(3) 0.003(2) 0.019(2) -0.013(2) C6 0.035(2) 0.032(2) 0.047(2) -0.0062(19) 0.0159(19) -0.0048(18) C7 0.042(2) 0.025(2) 0.058(3) 0.012(2) 0.011(2) 0.0044(18) C8 0.032(2) 0.022(2) 0.066(3) -0.0045(19) 0.016(2) -0.0034(17) C9 0.040(2) 0.030(2) 0.051(3) -0.0044(19) 0.011(2) 0.0051(19) C10 0.028(2) 0.035(2) 0.046(2) 0.0000(18) 0.0096(18) 0.0048(17) C11 0.030(2) 0.034(2) 0.053(3) -0.0010(19) 0.0090(19) -0.0054(18) Cl1 0.0483(6) 0.0318(5) 0.0639(7) -0.0051(5) 0.0178(5) 0.0046(5) Cl2 0.0799(9) 0.0289(5) 0.0753(8) 0.0060(5) 0.0391(7) -0.0016(5) N1 0.0322(18) 0.0251(17) 0.048(2) -0.0053(14) 0.0082(15) 0.0009(14) N2 0.0323(18) 0.0262(16) 0.0459(19) -0.0024(15) 0.0072(15) -0.0024(14) Pd1 0.03131(18) 0.02254(16) 0.03985(19) -0.00074(12) 0.00745(13) -0.00095(12) Se1 0.0392(2) 0.0329(2) 0.0365(2) 0.00316(17) 0.00493(18) -0.00243(17) _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 Br1 C10 1.865(4) . ? C1 C6 1.365(6) . ? C1 C2 1.384(6) . ? C1 H1 0.9300 . ? C2 C3 1.369(7) . ? C2 H2 0.9300 . ? C3 C4 1.365(7) . ? C3 H3 0.9300 . ? C4 C5 1.375(7) . ? C4 H4 0.9300 . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 Se1 1.934(4) . ? C7 C8 1.516(6) . ? C7 Se1 1.945(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.455(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N1 1.341(4) . ? C9 C10 1.366(5) . ? C9 H9 0.9300 . ? C10 C11 1.379(5) . ? C11 N2 1.342(4) . ? C11 H11 0.9300 . ? Cl1 Pd1 2.2867(11) . ? Cl2 Pd1 2.3152(11) . ? N1 N2 1.365(4) . ? N2 Pd1 2.035(3) . ? Pd1 Se1 2.3806(7) . ? 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 C6 C1 C2 119.9(4) . . ? C6 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C3 C2 C1 119.9(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.8(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 119.1(5) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 120.3(4) . . ? C1 C6 Se1 123.2(3) . . ? C5 C6 Se1 116.5(3) . . ? C8 C7 Se1 112.9(3) . . ? C8 C7 H7A 109.0 . . ? Se1 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? Se1 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C7 112.1(3) . . ? N1 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N1 C9 C10 107.3(3) . . ? N1 C9 H9 126.4 . . ? C10 C9 H9 126.4 . . ? C9 C10 C11 106.5(3) . . ? C9 C10 Br1 126.4(3) . . ? C11 C10 Br1 127.0(3) . . ? N2 C11 C10 110.0(3) . . ? N2 C11 H11 125.0 . . ? C10 C11 H11 125.0 . . ? C9 N1 N2 110.6(3) . . ? C9 N1 C8 126.6(3) . . ? N2 N1 C8 122.8(3) . . ? C11 N2 N1 105.6(3) . . ? C11 N2 Pd1 127.1(3) . . ? N1 N2 Pd1 126.4(2) . . ? N2 Pd1 Cl1 179.79(9) . . ? N2 Pd1 Cl2 89.82(9) . . ? Cl1 Pd1 Cl2 90.39(4) . . ? N2 Pd1 Se1 94.44(9) . . ? Cl1 Pd1 Se1 85.35(4) . . ? Cl2 Pd1 Se1 175.01(3) . . ? C6 Se1 C7 96.24(17) . . ? C6 Se1 Pd1 106.66(12) . . ? C7 Se1 Pd1 103.60(12) . . ? 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 C6 C1 C2 C3 -0.6(7) . . . . ? C1 C2 C3 C4 -1.2(8) . . . . ? C2 C3 C4 C5 1.6(8) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C2 C1 C6 C5 2.0(6) . . . . ? C2 C1 C6 Se1 -175.8(3) . . . . ? C4 C5 C6 C1 -1.5(7) . . . . ? C4 C5 C6 Se1 176.4(4) . . . . ? Se1 C7 C8 N1 77.9(3) . . . . ? N1 C9 C10 C11 0.6(5) . . . . ? N1 C9 C10 Br1 -176.5(3) . . . . ? C9 C10 C11 N2 -1.5(5) . . . . ? Br1 C10 C11 N2 175.5(3) . . . . ? C10 C9 N1 N2 0.5(4) . . . . ? C10 C9 N1 C8 179.7(4) . . . . ? C7 C8 N1 C9 123.9(4) . . . . ? C7 C8 N1 N2 -57.0(5) . . . . ? C10 C11 N2 N1 1.7(4) . . . . ? C10 C11 N2 Pd1 -167.9(3) . . . . ? C9 N1 N2 C11 -1.4(4) . . . . ? C8 N1 N2 C11 179.4(3) . . . . ? C9 N1 N2 Pd1 168.3(3) . . . . ? C8 N1 N2 Pd1 -10.9(5) . . . . ? C11 N2 Pd1 Cl2 24.2(3) . . . . ? N1 N2 Pd1 Cl2 -143.4(3) . . . . ? C11 N2 Pd1 Se1 -153.2(3) . . . . ? N1 N2 Pd1 Se1 39.2(3) . . . . ? C1 C6 Se1 C7 -107.4(3) . . . . ? C5 C6 Se1 C7 74.8(3) . . . . ? C1 C6 Se1 Pd1 -1.1(4) . . . . ? C5 C6 Se1 Pd1 -179.0(3) . . . . ? C8 C7 Se1 C6 74.7(3) . . . . ? C8 C7 Se1 Pd1 -34.2(3) . . . . ? N2 Pd1 Se1 C6 -113.61(15) . . . . ? Cl1 Pd1 Se1 C6 66.35(12) . . . . ? N2 Pd1 Se1 C7 -12.71(16) . . . . ? Cl1 Pd1 Se1 C7 167.25(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.425 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.099 data_complex_3 _database_code_depnum_ccdc_archive 'CCDC 885702' #TrackingRef 'Complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 Br2 Cl N4 Pd S, B F4, C2 H3 N' _chemical_formula_sum 'C12 H15 B Br2 Cl F4 N5 Pd S' _chemical_formula_weight 649.82 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' B B 0.0013 0.0007 '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' S S 0.1246 0.1234 '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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.540(1) _cell_length_b 10.626(1) _cell_length_c 13.770(2) _cell_angle_alpha 99.42(3) _cell_angle_beta 97.76(2) _cell_angle_gamma 104.37(2) _cell_volume 1036.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1394 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.01 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 2.082 _exptl_crystal_density_diffrn 2.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624.0 _exptl_absorpt_coefficient_mu 5.023 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.274 _exptl_absorpt_correction_T_max 0.429 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4469 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.1416 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3643 _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0946P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3643 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1672 _refine_ls_goodness_of_fit_ref 0.857 _refine_ls_restrained_S_all 0.857 _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 0.66126(11) 0.66101(10) 0.81143(8) 0.0533(4) Uani 1 1 d . . . S1 S 0.9282(4) 0.7688(4) 0.7644(3) 0.0674(10) Uani 1 1 d . . . N2 N 0.7684(12) 0.5088(10) 0.8280(8) 0.055(3) Uani 1 1 d . . . N1 N 0.8588(12) 0.4533(10) 0.7605(8) 0.058(3) Uani 1 1 d . . . N4 N 0.5553(12) 0.8136(10) 0.7954(8) 0.058(3) Uani 1 1 d . . . N3 N 0.5613(13) 0.8705(10) 0.7150(9) 0.060(3) Uani 1 1 d . . . N5 N 0.319(2) 0.4889(19) 0.5733(15) 0.134(7) Uani 1 1 d . . . Br1 Br 0.89657(19) 0.22115(15) 0.95898(13) 0.0817(5) Uani 1 1 d . . . Br2 Br 0.3024(2) 1.10228(17) 0.87192(14) 0.0910(6) Uani 1 1 d . . . Cl1 Cl 0.3989(4) 0.5612(3) 0.8685(3) 0.0662(9) Uani 1 1 d . . . C1 C 0.7612(15) 0.4394(13) 0.8976(12) 0.069(4) Uani 1 1 d . . . H1 H 0.7003 0.4516 0.9512 0.083 Uiso 1 1 calc R . . C2 C 0.8587(14) 0.3432(12) 0.8802(11) 0.059(3) Uani 1 1 d . . . C3 C 0.9115(16) 0.3516(14) 0.7904(11) 0.066(4) Uani 1 1 d . . . H3 H 0.9724 0.2974 0.7562 0.079 Uiso 1 1 calc R . . C4 C 0.8918(19) 0.5077(14) 0.6714(10) 0.070(4) Uani 1 1 d . . . H4A H 0.7742 0.5100 0.6343 0.085 Uiso 1 1 calc R . . H4B H 0.9436 0.4500 0.6284 0.085 Uiso 1 1 calc R . . C5 C 1.0204(16) 0.6425(15) 0.6976(14) 0.092(6) Uani 1 1 d . . . H5A H 1.0527 0.6688 0.6367 0.110 Uiso 1 1 calc R . . H5B H 1.1341 0.6403 0.7388 0.110 Uiso 1 1 calc R . . C6 C 0.8535(18) 0.8528(15) 0.6689(12) 0.082(5) Uani 1 1 d . . . H6A H 0.9054 0.9477 0.6933 0.099 Uiso 1 1 calc R . . H6B H 0.9055 0.8282 0.6104 0.099 Uiso 1 1 calc R . . C7 C 0.6445(18) 0.8240(15) 0.6371(12) 0.073(4) Uani 1 1 d . . . H7A H 0.6188 0.8658 0.5813 0.088 Uiso 1 1 calc R . . H7B H 0.5903 0.7290 0.6147 0.088 Uiso 1 1 calc R . . C8 C 0.4829(18) 0.9730(13) 0.7294(12) 0.069(4) Uani 1 1 d . . . H8 H 0.4733 1.0295 0.6853 0.083 Uiso 1 1 calc R . . C9 C 0.4222(15) 0.9803(12) 0.8159(11) 0.060(3) Uani 1 1 d . . . C10 C 0.4716(16) 0.8789(13) 0.8572(11) 0.064(3) Uani 1 1 d . . . H10 H 0.4492 0.8601 0.9187 0.076 Uiso 1 1 calc R . . C11 C 0.3434(19) 0.4012(19) 0.6048(14) 0.089(5) Uani 1 1 d . . . C12 C 0.3712(18) 0.2934(14) 0.6540(13) 0.079(4) Uani 1 1 d . . . H12A H 0.4763 0.2667 0.6349 0.118 Uiso 1 1 calc R . . H12B H 0.2618 0.2193 0.6340 0.118 Uiso 1 1 calc R . . H12C H 0.3935 0.3237 0.7252 0.118 Uiso 1 1 calc R . . B1 B 0.8085(16) 0.1356(15) 0.5383(12) 0.074(5) Uani 1 1 d D . . F1 F 0.6656(14) 0.1603(15) 0.5738(12) 0.180(6) Uani 1 1 d D . . F2 F 0.895(3) 0.2366(14) 0.5039(16) 0.275(12) Uani 1 1 d D . . F3 F 0.7750(15) 0.0208(11) 0.4721(9) 0.134(4) Uani 1 1 d D . . F4 F 0.9309(19) 0.1374(14) 0.6141(10) 0.180(6) Uani 1 1 d D . . 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 0.0530(5) 0.0605(7) 0.0506(6) 0.0257(5) 0.0118(4) 0.0127(4) S1 0.0574(18) 0.070(2) 0.074(3) 0.031(2) 0.0125(16) 0.0065(16) N2 0.058(5) 0.060(7) 0.046(6) 0.026(6) 0.014(5) 0.004(5) N1 0.060(6) 0.068(8) 0.054(7) 0.023(6) 0.020(5) 0.017(5) N4 0.066(6) 0.074(8) 0.043(6) 0.036(6) 0.016(5) 0.014(5) N3 0.066(6) 0.060(7) 0.064(8) 0.030(6) 0.007(5) 0.024(5) N5 0.151(14) 0.134(16) 0.127(16) 0.074(13) 0.019(11) 0.033(12) Br1 0.0875(10) 0.0792(12) 0.0921(12) 0.0433(10) 0.0162(8) 0.0314(8) Br2 0.1165(12) 0.0825(12) 0.0852(13) 0.0207(10) 0.0136(9) 0.0482(9) Cl1 0.0602(17) 0.080(2) 0.073(2) 0.0366(19) 0.0260(16) 0.0249(16) C1 0.056(7) 0.077(10) 0.089(12) 0.030(9) 0.028(7) 0.029(7) C2 0.048(6) 0.056(9) 0.064(10) 0.012(7) 0.000(6) 0.001(6) C3 0.069(8) 0.071(10) 0.066(10) 0.032(8) 0.011(7) 0.022(7) C4 0.086(9) 0.081(11) 0.049(9) 0.008(8) 0.028(7) 0.028(8) C5 0.050(7) 0.109(13) 0.141(16) 0.074(12) 0.033(8) 0.026(8) C6 0.089(10) 0.095(12) 0.089(12) 0.053(10) 0.042(9) 0.039(8) C7 0.095(10) 0.071(10) 0.066(10) 0.021(8) 0.019(8) 0.039(8) C8 0.092(9) 0.057(9) 0.065(10) 0.022(8) 0.013(8) 0.025(7) C9 0.059(7) 0.056(9) 0.066(10) 0.008(7) 0.006(6) 0.021(6) C10 0.069(8) 0.062(9) 0.056(9) 0.006(7) 0.012(7) 0.014(7) C11 0.073(9) 0.099(15) 0.090(14) 0.017(11) 0.018(8) 0.017(9) C12 0.076(9) 0.068(10) 0.085(12) 0.013(9) -0.003(8) 0.019(7) B1 0.035(7) 0.079(14) 0.095(15) 0.017(12) -0.002(8) -0.002(7) F1 0.094(7) 0.247(16) 0.187(14) 0.001(11) 0.055(8) 0.037(8) F2 0.48(3) 0.120(12) 0.30(2) 0.085(13) 0.30(2) 0.070(15) F3 0.153(9) 0.106(8) 0.112(9) -0.009(7) -0.030(7) 0.027(7) F4 0.192(12) 0.176(12) 0.132(11) -0.051(10) -0.060(9) 0.079(10) _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 N4 2.007(10) . ? Pd1 N2 2.010(10) . ? Pd1 S1 2.288(4) . ? Pd1 Cl1 2.305(4) . ? S1 C6 1.811(13) . ? S1 C5 1.835(16) . ? N2 C1 1.301(15) . ? N2 N1 1.367(14) . ? N1 C3 1.346(15) . ? N1 C4 1.467(16) . ? N4 C10 1.332(15) . ? N4 N3 1.348(13) . ? N3 C8 1.362(16) . ? N3 C7 1.397(17) . ? N5 C11 1.13(2) . ? Br1 C2 1.872(13) . ? Br2 C9 1.880(13) . ? C1 C2 1.409(17) . ? C1 H1 0.9300 . ? C2 C3 1.360(18) . ? C3 H3 0.9300 . ? C4 C5 1.473(19) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.517(17) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.331(19) . ? C8 H8 0.9300 . ? C9 C10 1.402(17) . ? C10 H10 0.9300 . ? C11 C12 1.47(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? B1 F4 1.291(14) . ? B1 F2 1.307(14) . ? B1 F1 1.308(13) . ? B1 F3 1.344(14) . ? 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 N4 Pd1 N2 179.7(5) . . ? N4 Pd1 S1 89.8(3) . . ? N2 Pd1 S1 90.0(3) . . ? N4 Pd1 Cl1 89.4(3) . . ? N2 Pd1 Cl1 90.8(3) . . ? S1 Pd1 Cl1 176.40(15) . . ? C6 S1 C5 104.3(8) . . ? C6 S1 Pd1 105.5(4) . . ? C5 S1 Pd1 107.7(4) . . ? C1 N2 N1 106.1(10) . . ? C1 N2 Pd1 129.7(9) . . ? N1 N2 Pd1 124.1(7) . . ? C3 N1 N2 110.8(11) . . ? C3 N1 C4 128.4(11) . . ? N2 N1 C4 120.7(10) . . ? C10 N4 N3 107.0(10) . . ? C10 N4 Pd1 129.6(8) . . ? N3 N4 Pd1 123.4(8) . . ? N4 N3 C8 108.3(11) . . ? N4 N3 C7 120.2(10) . . ? C8 N3 C7 131.4(11) . . ? N2 C1 C2 110.4(13) . . ? N2 C1 H1 124.8 . . ? C2 C1 H1 124.8 . . ? C3 C2 C1 105.6(12) . . ? C3 C2 Br1 126.5(11) . . ? C1 C2 Br1 127.8(11) . . ? N1 C3 C2 106.9(13) . . ? N1 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? N1 C4 C5 111.7(12) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C4 C5 S1 114.6(9) . . ? C4 C5 H5A 108.6 . . ? S1 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? S1 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 S1 115.5(9) . . ? C7 C6 H6A 108.4 . . ? S1 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? S1 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? N3 C7 C6 112.0(13) . . ? N3 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N3 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 N3 110.0(12) . . ? C9 C8 H8 125.0 . . ? N3 C8 H8 125.0 . . ? C8 C9 C10 104.7(12) . . ? C8 C9 Br2 127.7(11) . . ? C10 C9 Br2 127.6(12) . . ? N4 C10 C9 110.0(13) . . ? N4 C10 H10 125.0 . . ? C9 C10 H10 125.0 . . ? N5 C11 C12 175(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F4 B1 F2 101.5(16) . . ? F4 B1 F1 106.8(15) . . ? F2 B1 F1 110.1(14) . . ? F4 B1 F3 109.1(12) . . ? F2 B1 F3 111.6(15) . . ? F1 B1 F3 116.5(12) . . ? 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 N4 Pd1 S1 C6 -36.7(7) . . . . ? N2 Pd1 S1 C6 143.6(7) . . . . ? N4 Pd1 S1 C5 -147.6(6) . . . . ? N2 Pd1 S1 C5 32.7(6) . . . . ? S1 Pd1 N2 C1 138.5(11) . . . . ? Cl1 Pd1 N2 C1 -38.0(11) . . . . ? S1 Pd1 N2 N1 -45.2(8) . . . . ? Cl1 Pd1 N2 N1 138.3(8) . . . . ? C1 N2 N1 C3 -1.6(13) . . . . ? Pd1 N2 N1 C3 -178.7(8) . . . . ? C1 N2 N1 C4 -179.9(11) . . . . ? Pd1 N2 N1 C4 3.0(14) . . . . ? S1 Pd1 N4 C10 -132.1(10) . . . . ? Cl1 Pd1 N4 C10 44.4(10) . . . . ? S1 Pd1 N4 N3 46.9(8) . . . . ? Cl1 Pd1 N4 N3 -136.7(8) . . . . ? C10 N4 N3 C8 1.0(13) . . . . ? Pd1 N4 N3 C8 -178.1(8) . . . . ? C10 N4 N3 C7 179.1(11) . . . . ? Pd1 N4 N3 C7 -0.1(15) . . . . ? N1 N2 C1 C2 4.2(13) . . . . ? Pd1 N2 C1 C2 -179.0(8) . . . . ? N2 C1 C2 C3 -5.2(15) . . . . ? N2 C1 C2 Br1 178.3(8) . . . . ? N2 N1 C3 C2 -1.6(14) . . . . ? C4 N1 C3 C2 176.5(11) . . . . ? C1 C2 C3 N1 3.9(14) . . . . ? Br1 C2 C3 N1 -179.5(8) . . . . ? C3 N1 C4 C5 -112.2(14) . . . . ? N2 N1 C4 C5 65.7(14) . . . . ? N1 C4 C5 S1 -66.9(14) . . . . ? C6 S1 C5 C4 -100.4(12) . . . . ? Pd1 S1 C5 C4 11.4(13) . . . . ? C5 S1 C6 C7 108.1(12) . . . . ? Pd1 S1 C6 C7 -5.2(13) . . . . ? N4 N3 C7 C6 -68.1(15) . . . . ? C8 N3 C7 C6 109.4(15) . . . . ? S1 C6 C7 N3 64.9(15) . . . . ? N4 N3 C8 C9 -1.8(15) . . . . ? C7 N3 C8 C9 -179.5(13) . . . . ? N3 C8 C9 C10 1.7(15) . . . . ? N3 C8 C9 Br2 -179.7(8) . . . . ? N3 N4 C10 C9 0.0(13) . . . . ? Pd1 N4 C10 C9 179.1(8) . . . . ? C8 C9 C10 N4 -1.1(15) . . . . ? Br2 C9 C10 N4 -179.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.824 _refine_diff_density_min -1.084 _refine_diff_density_rms 0.153 data_complex_4 _database_code_depnum_ccdc_archive 'CCDC 885703' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 Br2 Cl N4 Pd Se, B F4' _chemical_formula_sum 'C10 H12 B Br2 Cl F4 N4 Pd Se' _chemical_formula_weight 655.66 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' B B 0.0013 0.0007 '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' Se Se -0.0929 2.2259 '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 ? _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' 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 15.142(4) _cell_length_b 11.090(3) _cell_length_c 11.001(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.924(5) _cell_angle_gamma 90.00 _cell_volume 1800.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2825 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 24.65 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.462 _exptl_crystal_size_mid 0.224 _exptl_crystal_size_min 0.175 _exptl_crystal_density_meas 2.419 _exptl_crystal_density_diffrn 2.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232.0 _exptl_absorpt_coefficient_mu 7.678 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.135 _exptl_absorpt_correction_T_max 0.264 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16766 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3169 _reflns_number_gt 2767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0541P)^2^+4.9386P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3169 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.186 _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 B1 B 0.9597(6) 0.7999(9) 0.8623(8) 0.060(2) Uani 1 1 d D . . Br1 Br 0.51429(6) 0.62092(7) 0.31660(9) 0.0665(3) Uani 1 1 d . . . Br2 Br 0.66924(5) -0.33666(7) 0.64057(8) 0.0580(2) Uani 1 1 d . . . C1 C 0.5881(4) 0.3838(5) 0.3773(6) 0.0368(13) Uani 1 1 d . . . H1 H 0.5328 0.3511 0.3837 0.044 Uiso 1 1 calc R . . C2 C 0.6024(4) 0.5015(6) 0.3474(6) 0.0402(14) Uani 1 1 d . . . C3 C 0.6928(4) 0.5121(6) 0.3497(6) 0.0419(14) Uani 1 1 d . . . H3 H 0.7228 0.5815 0.3339 0.050 Uiso 1 1 calc R . . C4 C 0.8238(4) 0.3668(6) 0.3939(7) 0.0456(16) Uani 1 1 d . . . H4A H 0.8430 0.3229 0.4716 0.055 Uiso 1 1 calc R . . H4B H 0.8620 0.4377 0.3979 0.055 Uiso 1 1 calc R . . C5 C 0.8352(5) 0.2883(6) 0.2871(7) 0.0499(17) Uani 1 1 d . . . H5A H 0.8992 0.2713 0.2965 0.060 Uiso 1 1 calc R . . H5B H 0.8154 0.3334 0.2103 0.060 Uiso 1 1 calc R . . C6 C 0.8665(5) 0.0217(6) 0.3452(7) 0.0488(17) Uani 1 1 d . . . H6A H 0.8570 -0.0532 0.2984 0.059 Uiso 1 1 calc R . . H6B H 0.9240 0.0548 0.3361 0.059 Uiso 1 1 calc R . . C7 C 0.8733(4) -0.0063(6) 0.4794(6) 0.0436(15) Uani 1 1 d . . . H7A H 0.9279 -0.0529 0.5104 0.052 Uiso 1 1 calc R . . H7B H 0.8788 0.0686 0.5260 0.052 Uiso 1 1 calc R . . C8 C 0.7958(5) -0.1823(6) 0.5545(6) 0.0433(15) Uani 1 1 d . . . H8 H 0.8452 -0.2335 0.5792 0.052 Uiso 1 1 calc R . . C9 C 0.7094(4) -0.2037(5) 0.5650(6) 0.0382(14) Uani 1 1 d . . . C10 C 0.6584(4) -0.1044(6) 0.5160(6) 0.0421(15) Uani 1 1 d . . . H10 H 0.5966 -0.0949 0.5105 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.60445(12) 0.16302(15) 0.58046(16) 0.0468(4) Uani 1 1 d . . . F1 F 0.8739(4) 0.8178(9) 0.8516(7) 0.148(3) Uani 1 1 d D . . F2 F 0.9602(7) 0.7225(11) 0.7758(10) 0.185(4) Uani 1 1 d D . . F3 F 1.0057(8) 0.8926(9) 0.8339(11) 0.194(5) Uani 1 1 d . . . F4 F 1.0007(5) 0.7406(7) 0.9609(9) 0.155(4) Uani 1 1 d D . . N2 N 0.7292(3) 0.4043(5) 0.3790(5) 0.0378(12) Uani 1 1 d . . . N1 N 0.6664(3) 0.3244(4) 0.3957(5) 0.0334(11) Uani 1 1 d . . . N4 N 0.7963(3) -0.0730(5) 0.5018(5) 0.0384(12) Uani 1 1 d . . . N3 N 0.7123(3) -0.0244(5) 0.4775(5) 0.0380(12) Uani 1 1 d . . . Pd1 Pd 0.68854(3) 0.14966(4) 0.43257(4) 0.03087(16) Uani 1 1 d . . . Se1 Se 0.76966(4) 0.13511(6) 0.27057(6) 0.03856(19) Uani 1 1 d . . . 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 B1 0.051(5) 0.071(6) 0.058(5) -0.003(5) 0.011(4) -0.003(5) Br1 0.0556(5) 0.0466(4) 0.0964(7) 0.0137(4) 0.0148(4) 0.0220(3) Br2 0.0567(5) 0.0452(4) 0.0742(5) 0.0181(4) 0.0194(4) 0.0025(3) C1 0.032(3) 0.038(3) 0.042(3) 0.001(3) 0.011(3) 0.005(3) C2 0.043(4) 0.034(3) 0.044(4) -0.001(3) 0.010(3) 0.012(3) C3 0.046(4) 0.031(3) 0.050(4) 0.002(3) 0.014(3) 0.002(3) C4 0.025(3) 0.049(4) 0.063(4) -0.001(3) 0.009(3) -0.003(3) C5 0.044(4) 0.041(4) 0.073(5) 0.009(3) 0.030(3) 0.001(3) C6 0.038(4) 0.047(4) 0.068(5) 0.006(3) 0.024(3) 0.012(3) C7 0.026(3) 0.049(4) 0.056(4) 0.004(3) 0.008(3) 0.000(3) C8 0.040(4) 0.040(3) 0.048(4) 0.008(3) 0.006(3) 0.013(3) C9 0.041(3) 0.032(3) 0.043(3) 0.004(3) 0.012(3) 0.002(3) C10 0.032(3) 0.039(3) 0.057(4) 0.003(3) 0.013(3) -0.002(3) Cl1 0.0529(10) 0.0460(9) 0.0488(9) 0.0073(7) 0.0269(8) 0.0115(7) F1 0.069(4) 0.258(10) 0.124(6) 0.064(6) 0.040(4) 0.065(5) F2 0.155(8) 0.210(11) 0.201(10) -0.085(9) 0.061(7) 0.024(8) F3 0.258(13) 0.122(7) 0.249(12) 0.029(7) 0.159(10) -0.065(7) F4 0.088(5) 0.144(7) 0.199(8) 0.076(6) -0.038(5) -0.024(5) N2 0.030(3) 0.036(3) 0.047(3) 0.002(2) 0.009(2) 0.000(2) N1 0.034(3) 0.029(2) 0.040(3) 0.001(2) 0.013(2) 0.002(2) N4 0.028(3) 0.041(3) 0.047(3) 0.004(2) 0.010(2) 0.005(2) N3 0.026(2) 0.037(3) 0.052(3) 0.001(2) 0.011(2) 0.006(2) Pd1 0.0255(3) 0.0307(3) 0.0377(3) 0.00123(18) 0.01002(19) 0.00424(16) Se1 0.0353(4) 0.0423(4) 0.0409(4) -0.0011(3) 0.0146(3) 0.0049(3) _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 B1 F2 1.283(11) . ? B1 F1 1.295(10) . ? B1 F4 1.300(10) . ? B1 F3 1.318(12) . ? Br1 C2 1.857(6) . ? Br2 C9 1.860(6) . ? C1 N1 1.331(8) . ? C1 C2 1.374(9) . ? C1 H1 0.9300 . ? C2 C3 1.368(9) . ? C3 N2 1.326(8) . ? C3 H3 0.9300 . ? C4 N2 1.466(8) . ? C4 C5 1.503(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 Se1 1.955(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.489(10) . ? C6 Se1 1.967(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.448(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.344(8) . ? C8 C9 1.360(9) . ? C8 H8 0.9300 . ? C9 C10 1.384(9) . ? C10 N3 1.337(8) . ? C10 H10 0.9300 . ? Cl1 Pd1 2.2840(16) . ? N2 N1 1.342(7) . ? N1 Pd1 1.993(5) . ? N4 N3 1.351(7) . ? N3 Pd1 2.005(5) . ? Pd1 Se1 2.3854(9) . ? 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 F2 B1 F1 102.0(9) . . ? F2 B1 F4 101.5(10) . . ? F1 B1 F4 115.8(9) . . ? F2 B1 F3 104.8(10) . . ? F1 B1 F3 115.5(10) . . ? F4 B1 F3 114.5(9) . . ? N1 C1 C2 108.9(6) . . ? N1 C1 H1 125.6 . . ? C2 C1 H1 125.6 . . ? C3 C2 C1 106.7(5) . . ? C3 C2 Br1 128.1(5) . . ? C1 C2 Br1 125.1(5) . . ? N2 C3 C2 106.6(6) . . ? N2 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? N2 C4 C5 110.9(6) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C4 C5 Se1 115.6(5) . . ? C4 C5 H5A 108.4 . . ? Se1 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? Se1 C5 H5B 108.4 . . ? H5A C5 H5B 107.4 . . ? C7 C6 Se1 115.2(4) . . ? C7 C6 H6A 108.5 . . ? Se1 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? Se1 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N4 C7 C6 113.3(5) . . ? N4 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? N4 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C9 107.0(5) . . ? N4 C8 H8 126.5 . . ? C9 C8 H8 126.5 . . ? C8 C9 C10 106.9(6) . . ? C8 C9 Br2 126.4(5) . . ? C10 C9 Br2 126.6(5) . . ? N3 C10 C9 109.0(5) . . ? N3 C10 H10 125.5 . . ? C9 C10 H10 125.5 . . ? C3 N2 N1 111.1(5) . . ? C3 N2 C4 128.7(6) . . ? N1 N2 C4 120.2(5) . . ? C1 N1 N2 106.7(5) . . ? C1 N1 Pd1 128.0(4) . . ? N2 N1 Pd1 125.3(4) . . ? C8 N4 N3 110.4(5) . . ? C8 N4 C7 128.0(5) . . ? N3 N4 C7 121.4(5) . . ? C10 N3 N4 106.7(5) . . ? C10 N3 Pd1 129.0(4) . . ? N4 N3 Pd1 122.8(4) . . ? N1 Pd1 N3 177.5(2) . . ? N1 Pd1 Cl1 89.23(14) . . ? N3 Pd1 Cl1 89.11(15) . . ? N1 Pd1 Se1 90.29(14) . . ? N3 Pd1 Se1 91.45(15) . . ? Cl1 Pd1 Se1 177.21(5) . . ? C5 Se1 C6 101.6(3) . . ? C5 Se1 Pd1 102.0(2) . . ? C6 Se1 Pd1 101.1(2) . . ? 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 N1 C1 C2 C3 -0.8(7) . . . . ? N1 C1 C2 Br1 -178.6(4) . . . . ? C1 C2 C3 N2 0.5(7) . . . . ? Br1 C2 C3 N2 178.2(5) . . . . ? N2 C4 C5 Se1 -63.1(7) . . . . ? Se1 C6 C7 N4 67.0(7) . . . . ? N4 C8 C9 C10 0.5(7) . . . . ? N4 C8 C9 Br2 -175.8(5) . . . . ? C8 C9 C10 N3 -0.5(8) . . . . ? Br2 C9 C10 N3 175.9(5) . . . . ? C2 C3 N2 N1 0.0(7) . . . . ? C2 C3 N2 C4 -179.9(6) . . . . ? C5 C4 N2 C3 -107.9(7) . . . . ? C5 C4 N2 N1 72.2(8) . . . . ? C2 C1 N1 N2 0.8(7) . . . . ? C2 C1 N1 Pd1 -176.5(4) . . . . ? C3 N2 N1 C1 -0.5(7) . . . . ? C4 N2 N1 C1 179.4(6) . . . . ? C3 N2 N1 Pd1 176.9(4) . . . . ? C4 N2 N1 Pd1 -3.2(8) . . . . ? C9 C8 N4 N3 -0.4(7) . . . . ? C9 C8 N4 C7 175.1(6) . . . . ? C6 C7 N4 C8 120.4(7) . . . . ? C6 C7 N4 N3 -64.5(8) . . . . ? C9 C10 N3 N4 0.2(7) . . . . ? C9 C10 N3 Pd1 -165.5(5) . . . . ? C8 N4 N3 C10 0.1(7) . . . . ? C7 N4 N3 C10 -175.8(6) . . . . ? C8 N4 N3 Pd1 166.9(4) . . . . ? C7 N4 N3 Pd1 -9.0(8) . . . . ? C1 N1 Pd1 Cl1 -47.2(5) . . . . ? N2 N1 Pd1 Cl1 136.0(5) . . . . ? C1 N1 Pd1 Se1 130.0(5) . . . . ? N2 N1 Pd1 Se1 -46.7(5) . . . . ? C10 N3 Pd1 Cl1 33.4(6) . . . . ? N4 N3 Pd1 Cl1 -130.3(5) . . . . ? C10 N3 Pd1 Se1 -143.9(6) . . . . ? N4 N3 Pd1 Se1 52.4(5) . . . . ? C4 C5 Se1 C6 -100.6(5) . . . . ? C4 C5 Se1 Pd1 3.5(6) . . . . ? C7 C6 Se1 C5 95.3(6) . . . . ? C7 C6 Se1 Pd1 -9.5(6) . . . . ? N1 Pd1 Se1 C5 38.3(3) . . . . ? N3 Pd1 Se1 C5 -140.0(3) . . . . ? N1 Pd1 Se1 C6 142.8(3) . . . . ? N3 Pd1 Se1 C6 -35.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.544 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.124