# Electronic Supplementary Material (ESI) for RSC Advances # 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_3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H29 Br2 N7 Pd' _chemical_formula_weight 597.67 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' 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 8.1484(11) _cell_length_b 18.284(2) _cell_length_c 15.475(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2305.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184.0 _exptl_absorpt_coefficient_mu 4.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.259 _exptl_absorpt_correction_T_max 0.710 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22406 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2099 _reflns_number_gt 1893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0938P)^2^+18.3282P] 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 2091 _refine_ls_number_parameters 133 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.93213(8) 0.7500 0.55910(4) 0.0251(3) Uani 1 2 d S . 1 Br1 Br 1.12650(9) 0.65090(4) 0.59773(5) 0.0394(3) Uani 1 1 d . . 1 N3 N 0.6360(8) 0.6556(3) 0.5769(4) 0.0350(14) Uani 1 1 d . . 1 N2 N 0.6170(8) 0.5899(4) 0.4580(4) 0.0453(16) Uani 1 1 d . . 1 N1 N 0.7511(8) 0.6366(3) 0.4569(4) 0.0345(13) Uani 1 1 d . . 1 C5 C 0.7662(8) 0.6757(3) 0.5288(4) 0.0276(13) Uani 1 1 d . . 1 C7 C 0.6010(9) 0.6791(4) 0.6665(4) 0.0356(15) Uani 1 1 d . . 1 H7A H 0.7045 0.6846 0.6968 0.043 Uiso 1 1 calc R . 1 H7B H 0.5400 0.6405 0.6952 0.043 Uiso 1 1 calc R . 1 C6 C 0.5511(9) 0.6029(4) 0.5324(6) 0.0425(18) Uani 1 1 d . . 1 H6 H 0.4577 0.5795 0.5531 0.051 Uiso 1 1 calc R . 1 C8 C 0.5051(13) 0.7500 0.6753(7) 0.037(2) Uani 1 2 d S . 1 H8A H 0.4519 0.7500 0.7313 0.045 Uiso 1 2 calc SR . 1 H8B H 0.4192 0.7500 0.6319 0.045 Uiso 1 2 calc SR . 1 C4 C 0.8636(9) 0.6341(4) 0.3834(5) 0.0364(16) Uani 1 1 d . . 1 H4A H 0.9349 0.6765 0.3851 0.044 Uiso 1 1 calc R . 1 H4B H 0.8009 0.6361 0.3302 0.044 Uiso 1 1 calc R . 1 C3 C 0.9673(10) 0.5654(4) 0.3837(5) 0.0429(18) Uani 1 1 d . . 1 H3A H 0.8960 0.5229 0.3822 0.052 Uiso 1 1 calc R . 1 H3B H 1.0303 0.5634 0.4368 0.052 Uiso 1 1 calc R . 1 C2 C 1.0840(12) 0.5626(5) 0.3071(6) 0.056(2) Uani 1 1 d . . 1 H2A H 1.0209 0.5639 0.2539 0.067 Uiso 1 1 calc R . 1 H2B H 1.1542 0.6054 0.3081 0.067 Uiso 1 1 calc R . 1 C1 C 1.1886(17) 0.4951(6) 0.3081(10) 0.098(5) Uani 1 1 d . . 1 H1A H 1.2549 0.4947 0.3593 0.147 Uiso 1 1 calc R . 1 H1B H 1.2582 0.4947 0.2580 0.147 Uiso 1 1 calc R . 1 H1C H 1.1195 0.4525 0.3075 0.147 Uiso 1 1 calc R . 1 C10 C 0.4632(17) 0.7500 0.3352(9) 0.061(3) Uani 1 2 d SD A 1 C9 C 0.331(2) 0.7500 0.3974(11) 0.089(5) Uani 1 2 d SD A 1 H9A H 0.2337 0.7702 0.3713 0.133 Uiso 0.50 1 calc PR A 1 H9B H 0.3610 0.7791 0.4465 0.133 Uiso 0.50 1 calc PR A 1 H9C H 0.3089 0.7008 0.4157 0.133 Uiso 0.50 1 calc PR A 1 N4 N 0.5604(19) 0.7500 0.2853(10) 0.086(4) Uani 1 2 d SD A 1 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 0.0236(4) 0.0264(4) 0.0252(4) 0.000 0.0012(3) 0.000 Br1 0.0347(5) 0.0330(4) 0.0506(5) 0.0016(3) -0.0058(3) 0.0052(3) N3 0.036(3) 0.035(3) 0.035(3) 0.002(2) 0.005(3) 0.000(3) N2 0.041(4) 0.048(4) 0.047(4) -0.012(3) 0.000(3) -0.010(3) N1 0.034(3) 0.037(3) 0.032(3) -0.006(2) 0.002(2) -0.005(3) C5 0.028(3) 0.022(3) 0.032(3) 0.005(3) 0.001(3) 0.002(3) C7 0.038(4) 0.039(4) 0.031(3) 0.003(3) 0.005(3) 0.000(3) C6 0.032(4) 0.037(4) 0.059(5) -0.007(4) -0.001(3) -0.012(3) C8 0.036(5) 0.042(6) 0.035(5) 0.000 0.015(4) 0.000 C4 0.044(4) 0.035(4) 0.029(3) -0.002(3) 0.005(3) 0.000(3) C3 0.052(5) 0.037(4) 0.040(4) 0.000(3) 0.011(3) 0.000(4) C2 0.065(6) 0.041(5) 0.061(5) -0.001(4) 0.022(4) 0.001(4) C1 0.101(9) 0.046(6) 0.147(12) 0.005(7) 0.075(9) 0.012(6) C10 0.061(9) 0.065(9) 0.058(8) 0.000 -0.006(7) 0.000 C9 0.076(12) 0.112(15) 0.079(11) 0.000 0.008(9) 0.000 N4 0.092(11) 0.076(9) 0.090(10) 0.000 0.010(9) 0.000 _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 C5 1.974(7) . ? Pd1 C5 1.974(7) 8_575 ? Pd1 Br1 2.4797(8) 8_575 ? Pd1 Br1 2.4797(8) . ? N3 C5 1.348(9) . ? N3 C6 1.372(10) . ? N3 C7 1.479(9) . ? N2 C6 1.292(11) . ? N2 N1 1.388(9) . ? N1 C5 1.328(9) . ? N1 C4 1.461(9) . ? C7 C8 1.519(9) . ? C8 C7 1.519(9) 8_575 ? C4 C3 1.514(11) . ? C3 C2 1.520(11) . ? C2 C1 1.501(14) . ? C10 N4 1.105(14) . ? C10 C9 1.448(15) . ? 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 C5 Pd1 C5 87.0(4) . 8_575 ? C5 Pd1 Br1 176.39(18) . 8_575 ? C5 Pd1 Br1 89.54(18) 8_575 8_575 ? C5 Pd1 Br1 89.54(18) . . ? C5 Pd1 Br1 176.39(19) 8_575 . ? Br1 Pd1 Br1 93.89(4) 8_575 . ? C5 N3 C6 108.1(6) . . ? C5 N3 C7 126.2(6) . . ? C6 N3 C7 125.3(6) . . ? C6 N2 N1 103.0(6) . . ? C5 N1 N2 113.2(6) . . ? C5 N1 C4 127.7(6) . . ? N2 N1 C4 119.0(6) . . ? N1 C5 N3 104.1(6) . . ? N1 C5 Pd1 129.3(5) . . ? N3 C5 Pd1 126.6(5) . . ? N3 C7 C8 115.5(7) . . ? N2 C6 N3 111.5(7) . . ? C7 C8 C7 117.1(9) . 8_575 ? N1 C4 C3 112.0(6) . . ? C4 C3 C2 112.0(7) . . ? C1 C2 C3 112.0(8) . . ? N4 C10 C9 177.4(18) . . ? 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 N2 N1 C5 0.8(9) . . . . ? C6 N2 N1 C4 176.3(7) . . . . ? N2 N1 C5 N3 -1.8(8) . . . . ? C4 N1 C5 N3 -176.8(7) . . . . ? N2 N1 C5 Pd1 -179.3(5) . . . . ? C4 N1 C5 Pd1 5.8(11) . . . . ? C6 N3 C5 N1 2.1(8) . . . . ? C7 N3 C5 N1 175.2(6) . . . . ? C6 N3 C5 Pd1 179.6(5) . . . . ? C7 N3 C5 Pd1 -7.2(10) . . . . ? C5 Pd1 C5 N1 100.5(6) 8_575 . . . ? Br1 Pd1 C5 N1 117(3) 8_575 . . . ? Br1 Pd1 C5 N1 -80.6(6) . . . . ? C5 Pd1 C5 N3 -76.4(6) 8_575 . . . ? Br1 Pd1 C5 N3 -59(3) 8_575 . . . ? Br1 Pd1 C5 N3 102.6(6) . . . . ? C5 N3 C7 C8 87.4(9) . . . . ? C6 N3 C7 C8 -100.6(9) . . . . ? N1 N2 C6 N3 0.5(9) . . . . ? C5 N3 C6 N2 -1.7(9) . . . . ? C7 N3 C6 N2 -175.0(7) . . . . ? N3 C7 C8 C7 -80.7(10) . . . 8_575 ? C5 N1 C4 C3 102.8(9) . . . . ? N2 N1 C4 C3 -71.8(9) . . . . ? N1 C4 C3 C2 179.8(7) . . . . ? C4 C3 C2 C1 179.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.704 _refine_diff_density_min -1.139 _refine_diff_density_rms 0.202 _database_code_depnum_ccdc_archive 'CCDC 909117' ####################################################################### # # 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_h #TrackingRef 'h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H24 Br2 N6 Pd' _chemical_formula_sum 'C14 H24 Br2 N6 Pd' _chemical_formula_weight 542.61 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' 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 16.0644(18) _cell_length_b 9.4857(11) _cell_length_c 13.3115(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.765(3) _cell_angle_gamma 90.00 _cell_volume 1992.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3876 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.08 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 4.949 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2422 _exptl_absorpt_correction_T_max 0.4377 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 'Bruker APEXII CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16867 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3314 _reflns_number_gt 2775 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0673P)^2^+140.4418P] 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 3314 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1493 _refine_ls_R_factor_gt 0.1349 _refine_ls_wR_factor_ref 0.3444 _refine_ls_wR_factor_gt 0.3353 _refine_ls_goodness_of_fit_ref 1.245 _refine_ls_restrained_S_all 1.245 _refine_ls_shift/su_max 0.000 _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 0.35041(12) 0.00867(17) 0.16871(12) 0.0434(6) Uani 1 1 d . . . Br1 Br 0.3942(2) -0.2414(2) 0.1664(2) 0.0602(8) Uani 1 1 d . . . Br2 Br 0.3432(2) -0.0008(3) 0.35280(19) 0.0649(9) Uani 1 1 d . . . N1 N 0.3391(14) 0.3262(19) 0.1286(14) 0.049(5) Uani 1 1 d . . . N2 N 0.2069(14) 0.3782(19) 0.1410(14) 0.050(5) Uani 1 1 d . . . N3 N 0.2257(14) 0.2395(19) 0.1640(14) 0.049(5) Uani 1 1 d . . . N4 N 0.4184(14) 0.1431(19) 0.0040(14) 0.049(5) Uani 1 1 d . . . N5 N 0.3597(14) 0.0485(19) -0.1440(14) 0.049(5) Uani 1 1 d . . . N6 N 0.3347(14) -0.0171(19) -0.0633(14) 0.049(5) Uani 1 1 d . . . C1 C 0.3034(18) 0.205(2) 0.1558(17) 0.049(6) Uani 1 1 d . . . C2 C 0.3639(17) 0.039(2) 0.0244(17) 0.049(6) Uani 1 1 d . . . C3 C 0.4728(17) 0.231(2) 0.0803(17) 0.049(6) Uani 1 1 d . . . H3A H 0.5204 0.2652 0.0522 0.059 Uiso 1 1 calc R . . H3B H 0.4948 0.1741 0.1401 0.059 Uiso 1 1 calc R . . C4 C 0.4236(17) 0.354(2) 0.1112(17) 0.049(6) Uani 1 1 d . . . H4A H 0.4562 0.3941 0.1733 0.059 Uiso 1 1 calc R . . H4B H 0.4197 0.4253 0.0583 0.059 Uiso 1 1 calc R . . C5 C 0.2753(17) 0.425(2) 0.1198(17) 0.049(6) Uani 1 1 d . . . H5 H 0.2819 0.5173 0.0999 0.059 Uiso 1 1 calc R . . C6 C 0.4131(17) 0.145(2) -0.0993(17) 0.049(6) Uani 1 1 d . . . H6 H 0.4430 0.2069 -0.1337 0.059 Uiso 1 1 calc R . . C7 C 0.280(2) -0.141(3) -0.086(2) 0.078(10) Uani 1 1 d . . . H7A H 0.2810 -0.1947 -0.0237 0.094 Uiso 1 1 calc R . . H7B H 0.3019 -0.2013 -0.1339 0.094 Uiso 1 1 calc R . . C8 C 0.188(2) -0.105(4) -0.131(3) 0.083(9) Uani 1 1 d . . . H8A H 0.1605 -0.1869 -0.1665 0.100 Uiso 1 1 calc R . . H8B H 0.1870 -0.0301 -0.1812 0.100 Uiso 1 1 calc R . . C9 C 0.139(2) -0.058(3) -0.049(2) 0.076(8) Uani 1 1 d . . . H9A H 0.0888 -0.0073 -0.0817 0.091 Uiso 1 1 calc R . . H9B H 0.1741 0.0060 -0.0028 0.091 Uiso 1 1 calc R . . C10 C 0.113(2) -0.182(3) 0.012(2) 0.076(9) Uani 1 1 d . . . H10A H 0.0612 -0.2227 -0.0252 0.114 Uiso 1 1 calc R . . H10B H 0.1040 -0.1495 0.0770 0.114 Uiso 1 1 calc R . . H10C H 0.1567 -0.2524 0.0211 0.114 Uiso 1 1 calc R . . C11 C 0.1589(17) 0.151(2) 0.1899(17) 0.050(6) Uani 1 1 d . . . H11A H 0.1792 0.0543 0.1980 0.059 Uiso 1 1 calc R . . H11B H 0.1108 0.1525 0.1337 0.059 Uiso 1 1 calc R . . C12 C 0.130(2) 0.197(4) 0.288(3) 0.082(9) Uani 1 1 d . . . H12A H 0.1031 0.2889 0.2778 0.098 Uiso 1 1 calc R . . H12B H 0.1780 0.2036 0.3433 0.098 Uiso 1 1 calc R . . C13 C 0.066(2) 0.088(3) 0.314(2) 0.076(8) Uani 1 1 d . . . H13A H 0.0233 0.0697 0.2540 0.091 Uiso 1 1 calc R . . H13B H 0.0954 0.0006 0.3346 0.091 Uiso 1 1 calc R . . C14 C 0.023(2) 0.138(4) 0.400(2) 0.078(9) Uani 1 1 d . . . H14A H 0.0620 0.1931 0.4476 0.117 Uiso 1 1 calc R . . H14B H 0.0047 0.0580 0.4341 0.117 Uiso 1 1 calc R . . H14C H -0.0254 0.1949 0.3718 0.117 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 0.0612(13) 0.0319(9) 0.0370(9) 0.0016(6) 0.0087(8) -0.0052(8) Br1 0.087(2) 0.0328(12) 0.0589(15) 0.0029(10) 0.0082(13) 0.0004(12) Br2 0.110(2) 0.0473(14) 0.0399(13) 0.0050(10) 0.0210(13) -0.0043(14) N1 0.075(16) 0.034(10) 0.041(10) 0.001(8) 0.018(10) 0.000(10) N2 0.076(16) 0.034(10) 0.042(10) 0.001(8) 0.018(10) 0.000(10) N3 0.075(16) 0.034(10) 0.041(10) 0.001(8) 0.018(10) 0.000(10) N4 0.075(15) 0.034(10) 0.041(10) 0.001(8) 0.018(9) 0.000(10) N5 0.076(15) 0.034(10) 0.041(10) 0.001(8) 0.018(9) 0.000(10) N6 0.075(15) 0.034(10) 0.041(10) 0.001(8) 0.018(9) 0.001(9) C1 0.075(19) 0.034(12) 0.041(12) 0.001(9) 0.018(12) 0.000(12) C2 0.075(18) 0.034(11) 0.041(12) 0.001(9) 0.018(11) 0.000(11) C3 0.075(18) 0.034(11) 0.041(12) 0.001(9) 0.018(11) 0.000(11) C4 0.076(19) 0.034(11) 0.041(12) 0.001(9) 0.018(11) 0.000(11) C5 0.076(19) 0.034(12) 0.041(12) 0.001(9) 0.018(12) 0.000(12) C6 0.076(19) 0.034(12) 0.041(12) 0.001(9) 0.019(11) 0.000(12) C7 0.13(3) 0.045(15) 0.053(15) -0.007(12) -0.002(17) -0.023(17) C8 0.08(3) 0.08(2) 0.08(2) 0.000(18) 0.016(18) 0.000(19) C9 0.08(2) 0.08(2) 0.075(19) 0.000(16) 0.014(16) 0.000(17) C10 0.08(2) 0.08(2) 0.076(19) 0.000(16) 0.014(16) 0.000(17) C11 0.075(18) 0.034(11) 0.042(12) 0.001(9) 0.018(11) 0.000(11) C12 0.08(2) 0.08(2) 0.08(2) 0.000(18) 0.016(17) 0.000(18) C13 0.08(2) 0.08(2) 0.076(19) 0.000(16) 0.014(16) 0.000(17) C14 0.08(2) 0.08(2) 0.08(2) 0.000(17) 0.015(17) 0.000(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 Pd1 C2 1.99(2) . ? Pd1 C1 2.00(2) . ? Pd1 Br1 2.476(3) . ? Pd1 Br2 2.477(3) . ? N1 C1 1.36(3) . ? N1 C5 1.38(3) . ? N1 C4 1.44(3) . ? N2 C5 1.26(3) . ? N2 N3 1.37(3) . ? N3 C1 1.31(3) . ? N3 C11 1.46(3) . ? N4 C6 1.36(3) . ? N4 C2 1.38(3) . ? N4 C3 1.47(3) . ? N5 C6 1.32(3) . ? N5 N6 1.37(3) . ? N6 C2 1.29(3) . ? N6 C7 1.47(3) . ? C3 C4 1.51(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.52(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.52(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.53(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.53(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.54(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.51(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C2 Pd1 C1 83.6(9) . . ? C2 Pd1 Br1 92.6(7) . . ? C1 Pd1 Br1 172.8(7) . . ? C2 Pd1 Br2 172.7(7) . . ? C1 Pd1 Br2 91.8(6) . . ? Br1 Pd1 Br2 92.52(10) . . ? C1 N1 C5 105(2) . . ? C1 N1 C4 131(2) . . ? C5 N1 C4 124.8(19) . . ? C5 N2 N3 103(2) . . ? C1 N3 N2 113(2) . . ? C1 N3 C11 129(2) . . ? N2 N3 C11 118(2) . . ? C6 N4 C2 106.7(19) . . ? C6 N4 C3 127(2) . . ? C2 N4 C3 125.9(18) . . ? C6 N5 N6 102.9(18) . . ? C2 N6 N5 114(2) . . ? C2 N6 C7 129(2) . . ? N5 N6 C7 117.1(19) . . ? N3 C1 N1 105(2) . . ? N3 C1 Pd1 125.0(17) . . ? N1 C1 Pd1 129.4(19) . . ? N6 C2 N4 104.8(19) . . ? N6 C2 Pd1 136.4(19) . . ? N4 C2 Pd1 118.8(16) . . ? N4 C3 C4 111(2) . . ? N4 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N4 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C3 117.2(19) . . ? N1 C4 H4A 108.0 . . ? C3 C4 H4A 108.0 . . ? N1 C4 H4B 108.0 . . ? C3 C4 H4B 108.0 . . ? H4A C4 H4B 107.2 . . ? N2 C5 N1 114(2) . . ? N2 C5 H5 122.9 . . ? N1 C5 H5 122.9 . . ? N5 C6 N4 111(2) . . ? N5 C6 H6 124.5 . . ? N4 C6 H6 124.5 . . ? N6 C7 C8 114(3) . . ? N6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C9 112(3) . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8B 109.2 . . ? C9 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 113(3) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 113(2) . . ? N3 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N3 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 109(3) . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? C14 C13 C12 112(3) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 C5 N2 N3 C1 0(3) . . . . ? C5 N2 N3 C11 -178.3(19) . . . . ? C6 N5 N6 C2 5(3) . . . . ? C6 N5 N6 C7 -175(2) . . . . ? N2 N3 C1 N1 2(3) . . . . ? C11 N3 C1 N1 179(2) . . . . ? N2 N3 C1 Pd1 -173.3(15) . . . . ? C11 N3 C1 Pd1 4(3) . . . . ? C5 N1 C1 N3 -2(2) . . . . ? C4 N1 C1 N3 178(2) . . . . ? C5 N1 C1 Pd1 172.6(17) . . . . ? C4 N1 C1 Pd1 -7(4) . . . . ? C2 Pd1 C1 N3 118(2) . . . . ? Br1 Pd1 C1 N3 59(6) . . . . ? Br2 Pd1 C1 N3 -67.6(19) . . . . ? C2 Pd1 C1 N1 -56(2) . . . . ? Br1 Pd1 C1 N1 -114(6) . . . . ? Br2 Pd1 C1 N1 119(2) . . . . ? N5 N6 C2 N4 -5(3) . . . . ? C7 N6 C2 N4 174(3) . . . . ? N5 N6 C2 Pd1 176(2) . . . . ? C7 N6 C2 Pd1 -4(5) . . . . ? C6 N4 C2 N6 4(3) . . . . ? C3 N4 C2 N6 -175(2) . . . . ? C6 N4 C2 Pd1 -177.6(17) . . . . ? C3 N4 C2 Pd1 4(3) . . . . ? C1 Pd1 C2 N6 -118(3) . . . . ? Br1 Pd1 C2 N6 56(3) . . . . ? Br2 Pd1 C2 N6 -169(4) . . . . ? C1 Pd1 C2 N4 64(2) . . . . ? Br1 Pd1 C2 N4 -122.3(18) . . . . ? Br2 Pd1 C2 N4 12(8) . . . . ? C6 N4 C3 C4 99(3) . . . . ? C2 N4 C3 C4 -83(3) . . . . ? C1 N1 C4 C3 25(3) . . . . ? C5 N1 C4 C3 -155(2) . . . . ? N4 C3 C4 N1 43(3) . . . . ? N3 N2 C5 N1 -1(3) . . . . ? C1 N1 C5 N2 2(3) . . . . ? C4 N1 C5 N2 -178(2) . . . . ? N6 N5 C6 N4 -2(3) . . . . ? C2 N4 C6 N5 -1(3) . . . . ? C3 N4 C6 N5 178(2) . . . . ? C2 N6 C7 C8 104(3) . . . . ? N5 N6 C7 C8 -76(3) . . . . ? N6 C7 C8 C9 -79(3) . . . . ? C7 C8 C9 C10 -78(4) . . . . ? C1 N3 C11 C12 119(3) . . . . ? N2 N3 C11 C12 -64(3) . . . . ? N3 C11 C12 C13 -174(2) . . . . ? C11 C12 C13 C14 -170(3) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 1.988 _refine_diff_density_min -3.076 _refine_diff_density_rms 0.295 _database_code_depnum_ccdc_archive 'CCDC 909118'