# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jwu-Ting Chen' _publ_contact_author_email JTCHEN@NTU.EDU.TW _publ_section_title ; Alternating Ethylene-Norbornene Co-polymerization Catalyzed by Cationic Organopalladium Complexes Bearing Hemi-labile Bidentate Ligands of alpha-Amino-Pyridines ; loop_ _publ_author_name 'Jwu-Ting Chen' 'Shou-Ling Huang' 'Ya-Chi Lin' 'Yi-Hung Liu' ; Shiuh-Tzung Liu ; 'Yu Wang' 'Kuo-Hsuan Yu' # Attachment 'cis-3a.cif' data_ic11192 _database_code_depnum_ccdc_archive 'CCDC 736875' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 B F4 N3 Pd' _chemical_formula_weight 399.52 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5470(2) _cell_length_b 11.2769(2) _cell_length_c 11.2845(2) _cell_angle_alpha 62.7900(11) _cell_angle_beta 78.0550(12) _cell_angle_gamma 78.4120(12) _cell_volume 829.36(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 16431 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 1.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6276 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.44 _reflns_number_total 3711 _reflns_number_gt 3201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1201P)^2^+0.1557P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.26(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3711 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1804 _refine_ls_wR_factor_gt 0.1658 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.013 _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 0.63116(4) 0.62483(3) 0.34332(3) 0.0688(3) Uani 1 1 d . . . N1 N 0.3793(6) 0.7488(4) 0.2972(4) 0.0705(9) Uani 1 1 d . . . N2 N 0.5892(7) 0.5816(4) 0.1949(4) 0.0729(10) Uani 1 1 d . . . H2 H 0.6168 0.4911 0.2246 0.087 Uiso 1 1 calc R . . N3 N 0.6861(8) 0.6889(5) 0.4697(5) 0.0831(12) Uani 1 1 d . . . C1 C 0.8604(9) 0.4905(7) 0.3788(7) 0.0916(16) Uani 1 1 d . . . H1A H 0.9421 0.5180 0.4137 0.137 Uiso 1 1 calc R . . H1B H 0.9191 0.4867 0.2963 0.137 Uiso 1 1 calc R . . H1C H 0.8283 0.4033 0.4430 0.137 Uiso 1 1 calc R . . C2 C 0.2968(8) 0.8448(6) 0.3380(6) 0.0848(13) Uani 1 1 d . . . H2A H 0.3514 0.8607 0.3953 0.102 Uiso 1 1 calc R . . C3 C 0.1339(9) 0.9196(6) 0.2966(7) 0.0922(16) Uani 1 1 d . . . H3A H 0.0786 0.9849 0.3257 0.111 Uiso 1 1 calc R . . C4 C 0.0552(9) 0.8960(7) 0.2121(9) 0.105(2) Uani 1 1 d . . . H4A H -0.0552 0.9446 0.1836 0.126 Uiso 1 1 calc R . . C5 C 0.1394(9) 0.8006(6) 0.1697(7) 0.0906(15) Uani 1 1 d . . . H5A H 0.0885 0.7855 0.1102 0.109 Uiso 1 1 calc R . . C6 C 0.3005(7) 0.7268(5) 0.2157(5) 0.0742(11) Uani 1 1 d . . . C7 C 0.3939(8) 0.6124(5) 0.1807(6) 0.0821(13) Uani 1 1 d . . . H7A H 0.3343 0.5327 0.2389 0.099 Uiso 1 1 calc R . . H7B H 0.3798 0.6358 0.0888 0.099 Uiso 1 1 calc R . . C8 C 0.7267(11) 0.6462(7) 0.0679(6) 0.1002(18) Uani 1 1 d . . . H8A H 0.8474 0.6263 0.0968 0.120 Uiso 1 1 calc R . . C9 C 0.6754(14) 0.8000(7) 0.0074(8) 0.118(3) Uani 1 1 d . . . H9A H 0.7595 0.8420 -0.0715 0.177 Uiso 1 1 calc R . . H9B H 0.6808 0.8316 0.0723 0.177 Uiso 1 1 calc R . . H9C H 0.5539 0.8223 -0.0162 0.177 Uiso 1 1 calc R . . C10 C 0.7386(13) 0.5891(9) -0.0285(7) 0.112(2) Uani 1 1 d . . . H10A H 0.8250 0.6318 -0.1056 0.168 Uiso 1 1 calc R . . H10B H 0.6210 0.6041 -0.0563 0.168 Uiso 1 1 calc R . . H10C H 0.7777 0.4944 0.0137 0.168 Uiso 1 1 calc R . . C11 C 0.7236(8) 0.7430(6) 0.5220(5) 0.0772(12) Uani 1 1 d . . . C12 C 0.7714(10) 0.8131(7) 0.5886(6) 0.0918(15) Uani 1 1 d . . . H12A H 0.7125 0.7793 0.6797 0.138 Uiso 1 1 calc R . . H12B H 0.7321 0.9074 0.5422 0.138 Uiso 1 1 calc R . . H12C H 0.9013 0.7991 0.5879 0.138 Uiso 1 1 calc R . . B1 B 0.7315(8) 0.1967(6) 0.2511(6) 0.0779(13) Uani 1 1 d . . . F1 F 0.5993(6) 0.3025(4) 0.2467(6) 0.1194(14) Uani 1 1 d . . . F2 F 0.8185(18) 0.2170(10) 0.1336(8) 0.262(6) Uani 1 1 d . . . F3 F 0.6570(11) 0.0852(7) 0.2903(14) 0.234(5) Uani 1 1 d . . . F4 F 0.8363(15) 0.1647(13) 0.3371(14) 0.281(7) 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 Pd1 0.0735(3) 0.0656(3) 0.0709(3) -0.0332(2) -0.01216(18) -0.00470(17) N1 0.073(2) 0.065(2) 0.073(2) -0.0304(18) -0.0070(17) -0.0073(17) N2 0.091(3) 0.0610(19) 0.071(2) -0.0336(17) -0.0077(19) -0.0094(18) N3 0.091(3) 0.086(3) 0.082(3) -0.042(2) -0.022(2) -0.005(2) C1 0.088(4) 0.088(3) 0.098(4) -0.044(3) -0.027(3) 0.014(3) C2 0.086(3) 0.083(3) 0.092(3) -0.050(3) -0.012(3) 0.002(3) C3 0.085(3) 0.082(3) 0.109(4) -0.050(3) -0.005(3) 0.003(3) C4 0.078(3) 0.078(3) 0.139(6) -0.031(4) -0.026(4) 0.003(3) C5 0.090(3) 0.073(3) 0.108(4) -0.032(3) -0.032(3) -0.006(3) C6 0.084(3) 0.060(2) 0.078(3) -0.025(2) -0.018(2) -0.013(2) C7 0.097(3) 0.068(2) 0.094(3) -0.041(2) -0.027(3) -0.006(2) C8 0.126(5) 0.088(4) 0.082(3) -0.037(3) -0.001(3) -0.016(3) C9 0.152(7) 0.085(4) 0.095(4) -0.022(3) 0.013(4) -0.041(4) C10 0.127(6) 0.124(5) 0.089(4) -0.051(4) -0.004(4) -0.024(5) C11 0.083(3) 0.081(3) 0.070(3) -0.033(2) -0.017(2) -0.007(2) C12 0.105(4) 0.100(4) 0.087(3) -0.050(3) -0.015(3) -0.022(3) B1 0.076(3) 0.076(3) 0.081(3) -0.036(3) -0.017(3) 0.004(2) F1 0.093(2) 0.083(2) 0.176(4) -0.061(3) -0.008(3) 0.0045(18) F2 0.352(14) 0.194(7) 0.143(5) -0.068(5) 0.028(7) 0.101(8) F3 0.150(5) 0.117(4) 0.443(16) -0.142(7) -0.026(7) 0.005(4) F4 0.258(10) 0.352(13) 0.389(14) -0.301(13) -0.227(11) 0.173(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 N3 2.008(5) . ? Pd1 C1 2.031(6) . ? Pd1 N2 2.042(4) . ? Pd1 N1 2.125(4) . ? N1 C6 1.326(7) . ? N1 C2 1.356(7) . ? N2 C7 1.470(8) . ? N2 C8 1.548(8) . ? N2 H2 0.9100 . ? N3 C11 1.127(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.379(9) . ? C2 H2A 0.9300 . ? C3 C4 1.365(11) . ? C3 H3A 0.9300 . ? C4 C5 1.363(10) . ? C4 H4A 0.9300 . ? C5 C6 1.379(8) . ? C5 H5A 0.9300 . ? C6 C7 1.517(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.477(10) . ? C8 C9 1.544(10) . ? C8 H8A 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.444(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? B1 F4 1.256(9) . ? B1 F2 1.290(9) . ? B1 F3 1.329(9) . ? B1 F1 1.382(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 N3 Pd1 C1 89.9(3) . . ? N3 Pd1 N2 172.44(17) . . ? C1 Pd1 N2 91.5(2) . . ? N3 Pd1 N1 97.3(2) . . ? C1 Pd1 N1 172.3(2) . . ? N2 Pd1 N1 81.71(18) . . ? C6 N1 C2 118.8(5) . . ? C6 N1 Pd1 112.7(3) . . ? C2 N1 Pd1 128.5(4) . . ? C7 N2 C8 118.0(5) . . ? C7 N2 Pd1 109.0(3) . . ? C8 N2 Pd1 109.7(4) . . ? C7 N2 H2 106.5 . . ? C8 N2 H2 106.5 . . ? Pd1 N2 H2 106.5 . . ? C11 N3 Pd1 168.7(5) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.6(6) . . ? N1 C2 H2A 119.2 . . ? C3 C2 H2A 119.2 . . ? C4 C3 C2 118.8(6) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 119.7(6) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 119.5(6) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? N1 C6 C5 121.6(5) . . ? N1 C6 C7 116.1(4) . . ? C5 C6 C7 122.2(5) . . ? N2 C7 C6 112.8(4) . . ? N2 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C10 C8 C9 113.7(7) . . ? C10 C8 N2 112.2(6) . . ? C9 C8 N2 108.3(6) . . ? C10 C8 H8A 107.5 . . ? C9 C8 H8A 107.5 . . ? N2 C8 H8A 107.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 179.7(7) . . ? 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 112.7(10) . . ? F4 B1 F3 103.6(10) . . ? F2 B1 F3 103.9(9) . . ? F4 B1 F1 112.9(6) . . ? F2 B1 F1 112.0(6) . . ? F3 B1 F1 111.0(6) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.115 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.211 # Attachment 'cis-3a.cif' data_ic10980 _database_code_depnum_ccdc_archive 'CCDC 736876' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H17 Cl N2 Pd' _chemical_formula_weight 307.11 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' 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 P2(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 8.7000(4) _cell_length_b 9.7343(4) _cell_length_c 14.2066(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.140(3) _cell_angle_gamma 90.00 _cell_volume 1201.33(9) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 31163 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.732 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6926 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2704 _reflns_number_gt 2167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0726P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.075(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2704 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 0.50223(3) 0.42761(3) 0.11145(2) 0.0479(2) Uani 1 1 d . . . Cl1 Cl 0.74637(12) 0.33187(14) 0.10048(10) 0.0686(4) Uani 1 1 d . . . N1 N 0.3792(3) 0.2387(4) 0.0896(3) 0.0506(8) Uani 1 1 d . . . N2 N 0.2784(3) 0.5045(3) 0.1108(2) 0.0472(8) Uani 1 1 d . . . H2 H 0.2771 0.5768 0.0701 0.057 Uiso 1 1 calc R . . C1 C 0.5930(5) 0.6149(5) 0.1426(3) 0.0580(11) Uani 1 1 d . . . H1A H 0.5115 0.6793 0.1511 0.087 Uiso 1 1 calc R . . H1B H 0.6533 0.6450 0.0918 0.087 Uiso 1 1 calc R . . H1C H 0.6574 0.6090 0.1995 0.087 Uiso 1 1 calc R . . C2 C 0.4322(6) 0.1098(5) 0.0970(4) 0.0650(12) Uani 1 1 d . . . H2A H 0.5380 0.0964 0.1043 0.078 Uiso 1 1 calc R . . C3 C 0.3396(7) -0.0024(5) 0.0944(4) 0.0792(16) Uani 1 1 d . . . H3A H 0.3808 -0.0905 0.0982 0.095 Uiso 1 1 calc R . . C4 C 0.1816(7) 0.0180(6) 0.0860(5) 0.0843(17) Uani 1 1 d . . . H4A H 0.1148 -0.0566 0.0861 0.101 Uiso 1 1 calc R . . C5 C 0.1250(5) 0.1480(6) 0.0776(4) 0.0682(13) Uani 1 1 d . . . H5A H 0.0194 0.1629 0.0707 0.082 Uiso 1 1 calc R . . C6 C 0.2257(4) 0.2576(4) 0.0793(3) 0.0481(9) Uani 1 1 d . . . C7 C 0.1723(5) 0.4028(4) 0.0659(3) 0.0522(10) Uani 1 1 d . . . H7A H 0.1605 0.4221 -0.0011 0.063 Uiso 1 1 calc R . . H7B H 0.0721 0.4127 0.0919 0.063 Uiso 1 1 calc R . . C8 C 0.0746(5) 0.6400(6) 0.1875(4) 0.0735(14) Uani 1 1 d . . . H8A H 0.0842 0.7092 0.1400 0.110 Uiso 1 1 calc R . . H8B H 0.0500 0.6826 0.2457 0.110 Uiso 1 1 calc R . . H8C H -0.0058 0.5770 0.1678 0.110 Uiso 1 1 calc R . . C9 C 0.2255(5) 0.5626(4) 0.2016(4) 0.0539(11) Uani 1 1 d . . . H9A H 0.3034 0.6291 0.2244 0.065 Uiso 1 1 calc R . . C10 C 0.2186(6) 0.4511(5) 0.2759(4) 0.0660(13) Uani 1 1 d . . . H10A H 0.3162 0.4051 0.2824 0.099 Uiso 1 1 calc R . . H10B H 0.1398 0.3861 0.2572 0.099 Uiso 1 1 calc R . . H10C H 0.1956 0.4917 0.3351 0.099 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 0.0350(2) 0.0528(3) 0.0561(3) 0.00224(13) 0.00418(15) -0.00116(11) Cl1 0.0390(5) 0.0737(8) 0.0938(9) 0.0203(7) 0.0090(5) 0.0073(5) N1 0.0429(16) 0.055(2) 0.054(2) -0.0005(16) 0.0070(14) 0.0020(15) N2 0.0410(17) 0.044(2) 0.057(2) 0.0044(15) 0.0038(15) 0.0005(13) C1 0.049(2) 0.062(3) 0.064(3) -0.004(2) 0.007(2) -0.012(2) C2 0.058(3) 0.062(3) 0.075(3) -0.005(3) 0.008(2) 0.008(2) C3 0.085(4) 0.049(3) 0.103(5) 0.001(3) 0.004(3) 0.006(3) C4 0.083(4) 0.054(3) 0.115(5) -0.007(3) 0.003(3) -0.017(3) C5 0.053(3) 0.066(3) 0.086(4) -0.008(3) 0.006(2) -0.010(2) C6 0.0431(19) 0.053(2) 0.049(2) -0.0010(18) 0.0040(16) -0.0050(17) C7 0.035(2) 0.058(2) 0.063(3) -0.003(2) 0.0015(18) 0.0005(17) C8 0.062(3) 0.070(3) 0.088(4) -0.011(3) 0.009(3) 0.016(2) C9 0.047(2) 0.048(3) 0.068(3) -0.0096(19) 0.010(2) 0.0016(16) C10 0.070(3) 0.064(3) 0.064(3) -0.001(2) 0.010(2) -0.002(2) _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 C1 2.026(5) . ? Pd1 N2 2.086(3) . ? Pd1 N1 2.141(4) . ? Pd1 Cl1 2.3325(11) . ? N1 C2 1.340(6) . ? N1 C6 1.348(5) . ? N2 C7 1.474(5) . ? N2 C9 1.504(6) . ? N2 H2 0.9100 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.356(8) . ? C2 H2A 0.9300 . ? C3 C4 1.387(8) . ? C3 H3A 0.9300 . ? C4 C5 1.360(9) . ? C4 H4A 0.9300 . ? C5 C6 1.380(6) . ? C5 H5A 0.9300 . ? C6 C7 1.496(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.517(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.518(7) . ? C9 H9A 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 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 C1 Pd1 N2 91.77(16) . . ? C1 Pd1 N1 171.89(15) . . ? N2 Pd1 N1 81.28(12) . . ? C1 Pd1 Cl1 91.63(14) . . ? N2 Pd1 Cl1 175.17(10) . . ? N1 Pd1 Cl1 95.57(9) . . ? C2 N1 C6 118.1(4) . . ? C2 N1 Pd1 128.8(3) . . ? C6 N1 Pd1 112.5(3) . . ? C7 N2 C9 114.2(3) . . ? C7 N2 Pd1 108.9(2) . . ? C9 N2 Pd1 117.4(3) . . ? C7 N2 H2 105.0 . . ? C9 N2 H2 105.1 . . ? Pd1 N2 H2 105.0 . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 123.5(5) . . ? N1 C2 H2A 118.3 . . ? C3 C2 H2A 118.3 . . ? C2 C3 C4 118.1(5) . . ? C2 C3 H3A 120.9 . . ? C4 C3 H3A 120.9 . . ? C5 C4 C3 119.5(5) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.3 . . ? N1 C6 C5 121.4(4) . . ? N1 C6 C7 116.2(3) . . ? C5 C6 C7 122.4(4) . . ? N2 C7 C6 113.4(3) . . ? N2 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C8 112.1(4) . . ? N2 C9 C10 110.7(3) . . ? C8 C9 C10 112.3(4) . . ? N2 C9 H9A 107.1 . . ? C8 C9 H9A 107.1 . . ? C10 C9 H9A 107.1 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.813 _refine_diff_density_min -1.223 _refine_diff_density_rms 0.319 # Attachment 'cis-3b.cif' data_ic11369 _database_code_depnum_ccdc_archive 'CCDC 736877' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 B F4 N3 Pd' _chemical_formula_weight 413.55 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' 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3568(4) _cell_length_b 13.8579(4) _cell_length_c 21.9950(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3461.60(19) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 14894 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 1.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 0.764 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19197 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3953 _reflns_number_gt 2511 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0870P)^2^+1.8472P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0131(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3953 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0929 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.54279(3) 0.17031(3) 0.725681(16) 0.0539(2) Uani 1 1 d . . . N1 N 0.6872(4) 0.0764(3) 0.70966(18) 0.0564(10) Uani 1 1 d . . . N2 N 0.5352(4) 0.1615(3) 0.6322(2) 0.0546(10) Uani 1 1 d . . . N3 N 0.5563(4) 0.1774(3) 0.8168(2) 0.0622(12) Uani 1 1 d . . . C1 C 0.4030(6) 0.2597(4) 0.7304(2) 0.0726(15) Uani 1 1 d . . . H1A H 0.3876 0.2755 0.7722 0.109 Uiso 1 1 calc R . . H1B H 0.3352 0.2285 0.7133 0.109 Uiso 1 1 calc R . . H1C H 0.4195 0.3177 0.7081 0.109 Uiso 1 1 calc R . . C2 C 0.7408(6) 0.0158(4) 0.7490(3) 0.0667(13) Uani 1 1 d . . . H2A H 0.7151 0.0136 0.7891 0.080 Uiso 1 1 calc R . . C3 C 0.8315(6) -0.0421(4) 0.7314(3) 0.0747(16) Uani 1 1 d . . . H3A H 0.8659 -0.0842 0.7591 0.090 Uiso 1 1 calc R . . C4 C 0.8719(5) -0.0382(4) 0.6727(3) 0.0736(15) Uani 1 1 d . . . H4A H 0.9359 -0.0754 0.6607 0.088 Uiso 1 1 calc R . . C5 C 0.8160(4) 0.0218(3) 0.6319(2) 0.0621(12) Uani 1 1 d . . . H5A H 0.8407 0.0242 0.5916 0.074 Uiso 1 1 calc R . . C6 C 0.7232(4) 0.0783(3) 0.6513(2) 0.0536(11) Uani 1 1 d . . . C7 C 0.6582(4) 0.1461(4) 0.6096(2) 0.0562(12) Uani 1 1 d . . . H7A H 0.6548 0.1176 0.5689 0.067 Uiso 1 1 calc R . . C8 C 0.7215(5) 0.2422(4) 0.6059(3) 0.0699(14) Uani 1 1 d . . . H8A H 0.6791 0.2846 0.5792 0.105 Uiso 1 1 calc R . . H8B H 0.7996 0.2324 0.5905 0.105 Uiso 1 1 calc R . . H8C H 0.7258 0.2704 0.6457 0.105 Uiso 1 1 calc R . . C9 C 0.4458(4) 0.0909(4) 0.6082(2) 0.0634(13) Uani 1 1 d . . . H9A H 0.3719 0.1031 0.6298 0.076 Uiso 1 1 calc R . . C10 C 0.4225(6) 0.1093(5) 0.5410(3) 0.0800(16) Uani 1 1 d . . . H10A H 0.3665 0.0631 0.5262 0.120 Uiso 1 1 calc R . . H10B H 0.4948 0.1032 0.5187 0.120 Uiso 1 1 calc R . . H10C H 0.3916 0.1733 0.5358 0.120 Uiso 1 1 calc R . . C11 C 0.4805(5) -0.0121(4) 0.6211(3) 0.0749(15) Uani 1 1 d . . . H11A H 0.4945 -0.0198 0.6639 0.112 Uiso 1 1 calc R . . H11B H 0.5508 -0.0276 0.5990 0.112 Uiso 1 1 calc R . . H11C H 0.4181 -0.0545 0.6087 0.112 Uiso 1 1 calc R . . C12 C 0.5665(5) 0.1797(4) 0.8671(3) 0.0620(13) Uani 1 1 d . . . C13 C 0.5767(6) 0.1825(5) 0.9331(3) 0.0814(17) Uani 1 1 d . . . H13A H 0.5989 0.2463 0.9457 0.122 Uiso 1 1 calc R . . H13B H 0.6355 0.1372 0.9460 0.122 Uiso 1 1 calc R . . H13C H 0.5023 0.1659 0.9510 0.122 Uiso 1 1 calc R . . B1 B 0.6516(6) -0.1017(5) 0.9344(3) 0.0722(17) Uani 1 1 d . . . F1 F 0.5473(4) -0.1504(3) 0.9292(2) 0.1106(14) Uani 1 1 d . . . F2 F 0.6653(4) -0.0324(3) 0.89329(19) 0.1194(14) Uani 1 1 d . . . F3 F 0.6776(8) -0.0773(7) 0.9862(2) 0.254(5) Uani 1 1 d . . . F4 F 0.7342(7) -0.1665(5) 0.9176(6) 0.268(6) Uani 1 1 d . . . H2 H 0.519(4) 0.209(4) 0.621(2) 0.036(14) Uiso 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 Pd1 0.0617(3) 0.0572(3) 0.0428(3) -0.00519(15) 0.00790(15) -0.00162(17) N1 0.064(3) 0.057(2) 0.048(2) -0.0070(18) 0.0009(19) -0.0012(19) N2 0.061(3) 0.057(3) 0.046(2) -0.002(2) 0.0020(18) 0.000(2) N3 0.074(3) 0.068(3) 0.045(3) -0.0069(19) 0.0099(19) -0.002(2) C1 0.073(4) 0.078(4) 0.066(3) -0.008(3) 0.016(3) 0.011(3) C2 0.084(4) 0.061(3) 0.055(3) 0.000(3) -0.005(3) 0.002(3) C3 0.085(4) 0.060(3) 0.079(4) 0.000(3) -0.025(3) 0.008(3) C4 0.066(3) 0.064(3) 0.090(4) -0.016(3) -0.007(3) 0.006(3) C5 0.062(3) 0.058(3) 0.066(3) -0.006(2) 0.013(2) 0.001(2) C6 0.058(3) 0.053(2) 0.050(3) -0.008(2) 0.005(2) -0.004(2) C7 0.057(3) 0.062(3) 0.049(3) -0.002(2) 0.008(2) -0.001(2) C8 0.067(3) 0.066(3) 0.076(4) 0.013(3) 0.008(3) -0.003(3) C9 0.057(3) 0.081(4) 0.052(3) -0.010(2) -0.001(2) -0.008(3) C10 0.093(4) 0.082(4) 0.065(3) -0.011(3) -0.015(3) -0.002(3) C11 0.084(4) 0.068(3) 0.073(4) 0.001(3) -0.001(3) -0.018(3) C12 0.065(3) 0.070(3) 0.051(3) -0.010(2) 0.011(2) -0.002(2) C13 0.095(4) 0.097(5) 0.052(3) -0.006(3) 0.004(3) -0.002(4) B1 0.074(4) 0.078(4) 0.064(4) 0.009(3) -0.012(3) -0.004(4) F1 0.104(3) 0.119(3) 0.108(3) 0.009(3) -0.010(2) -0.036(2) F2 0.132(3) 0.117(3) 0.109(3) 0.044(3) 0.002(3) -0.017(3) F3 0.316(10) 0.377(12) 0.071(3) 0.027(5) -0.050(4) -0.212(9) F4 0.136(5) 0.168(7) 0.50(2) 0.046(7) 0.053(8) 0.051(5) _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 N3 2.013(5) . ? Pd1 C1 2.017(6) . ? Pd1 N2 2.061(5) . ? Pd1 N1 2.123(4) . ? N1 C6 1.348(6) . ? N1 C2 1.351(7) . ? N2 C7 1.498(6) . ? N2 C9 1.506(6) . ? N2 H2 0.73(5) . ? N3 C12 1.112(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.362(9) . ? C2 H2A 0.9300 . ? C3 C4 1.370(8) . ? C3 H3A 0.9300 . ? C4 C5 1.379(8) . ? C4 H4A 0.9300 . ? C5 C6 1.380(6) . ? C5 H5A 0.9300 . ? C6 C7 1.506(7) . ? C7 C8 1.515(7) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C11 1.508(8) . ? C9 C10 1.522(8) . ? C9 H9A 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.457(8) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? B1 F3 1.223(8) . ? B1 F2 1.328(7) . ? B1 F4 1.351(10) . ? B1 F1 1.368(8) . ? 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 N3 Pd1 C1 88.75(19) . . ? N3 Pd1 N2 177.96(17) . . ? C1 Pd1 N2 93.2(2) . . ? N3 Pd1 N1 97.85(16) . . ? C1 Pd1 N1 173.40(18) . . ? N2 Pd1 N1 80.24(17) . . ? C6 N1 C2 119.0(4) . . ? C6 N1 Pd1 112.4(3) . . ? C2 N1 Pd1 128.5(4) . . ? C7 N2 C9 114.8(4) . . ? C7 N2 Pd1 107.5(3) . . ? C9 N2 Pd1 114.7(3) . . ? C7 N2 H2 105(4) . . ? C9 N2 H2 107(4) . . ? Pd1 N2 H2 107(4) . . ? C12 N3 Pd1 178.0(5) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.7(5) . . ? N1 C2 H2A 119.2 . . ? C3 C2 H2A 119.2 . . ? C2 C3 C4 119.8(5) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? N1 C6 C5 121.0(5) . . ? N1 C6 C7 116.3(4) . . ? C5 C6 C7 122.7(4) . . ? N2 C7 C6 110.1(4) . . ? N2 C7 C8 109.5(4) . . ? C6 C7 C8 110.4(4) . . ? N2 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C11 111.9(4) . . ? N2 C9 C10 110.4(5) . . ? C11 C9 C10 112.8(5) . . ? N2 C9 H9A 107.1 . . ? C11 C9 H9A 107.1 . . ? C10 C9 H9A 107.1 . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 178.5(6) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F3 B1 F2 113.9(7) . . ? F3 B1 F4 105.7(8) . . ? F2 B1 F4 102.3(7) . . ? F3 B1 F1 115.1(7) . . ? F2 B1 F1 113.6(5) . . ? F4 B1 F1 104.5(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.069 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.167 # Attachment 'cis-4b.cif' data_ic11164 _database_code_depnum_ccdc_archive 'CCDC 736878' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H21 Cl N2 Pd' _chemical_formula_weight 335.16 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' 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.19000(10) _cell_length_b 10.12680(10) _cell_length_c 15.3491(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1428.47(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 30408 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9298 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3239 _reflns_number_gt 3182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0278P)^2^+0.1776P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0132(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.33(2) _refine_ls_number_reflns 3239 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0185 _refine_ls_R_factor_gt 0.0156 _refine_ls_wR_factor_ref 0.0466 _refine_ls_wR_factor_gt 0.0419 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.489723(15) 0.102296(12) 0.163501(8) 0.02912(6) Uani 1 1 d . . . Cl1 Cl 0.66441(6) -0.05629(5) 0.13340(4) 0.04288(14) Uani 1 1 d . . . N1 N 0.30948(18) -0.01766(17) 0.12379(11) 0.0350(4) Uani 1 1 d . . . N2 N 0.31670(18) 0.23443(16) 0.18547(11) 0.0322(4) Uani 1 1 d . . . H2 H 0.3419 0.2842 0.2325 0.039 Uiso 1 1 calc R . . C1 C 0.6446(3) 0.2222(2) 0.21332(16) 0.0464(5) Uani 1 1 d . . . H1A H 0.6007 0.3029 0.2328 0.070 Uiso 1 1 calc R . . H1B H 0.7156 0.2413 0.1692 0.070 Uiso 1 1 calc R . . H1C H 0.6911 0.1792 0.2616 0.070 Uiso 1 1 calc R . . C2 C 0.3082(3) -0.1253(2) 0.07335(15) 0.0435(5) Uani 1 1 d . . . H2A H 0.3960 -0.1579 0.0522 0.052 Uiso 1 1 calc R . . C3 C 0.1808(3) -0.1897(3) 0.05160(16) 0.0551(6) Uani 1 1 d . . . H3A H 0.1823 -0.2641 0.0161 0.066 Uiso 1 1 calc R . . C4 C 0.0526(3) -0.1418(3) 0.08327(18) 0.0591(7) Uani 1 1 d . . . H4A H -0.0344 -0.1839 0.0697 0.071 Uiso 1 1 calc R . . C5 C 0.0519(2) -0.0304(3) 0.13571(16) 0.0506(6) Uani 1 1 d . . . H5A H -0.0347 0.0034 0.1577 0.061 Uiso 1 1 calc R . . C6 C 0.1835(2) 0.0288(2) 0.15444(14) 0.0370(4) Uani 1 1 d . . . C7 C 0.1948(2) 0.1473(2) 0.21394(14) 0.0372(4) Uani 1 1 d . . . H7A H 0.1035 0.1970 0.2118 0.045 Uiso 1 1 calc R . . C8 C 0.2224(3) 0.1014(2) 0.30759(14) 0.0475(5) Uani 1 1 d . . . H8A H 0.2285 0.1769 0.3452 0.071 Uiso 1 1 calc R . . H8B H 0.3121 0.0530 0.3100 0.071 Uiso 1 1 calc R . . H8C H 0.1439 0.0457 0.3262 0.071 Uiso 1 1 calc R . . C9 C 0.2821(3) 0.3307(2) 0.11173(14) 0.0420(5) Uani 1 1 d . . . C10 C 0.1461(3) 0.4114(3) 0.1334(2) 0.0659(7) Uani 1 1 d . . . H10A H 0.0639 0.3534 0.1382 0.099 Uiso 1 1 calc R . . H10B H 0.1288 0.4745 0.0878 0.099 Uiso 1 1 calc R . . H10C H 0.1604 0.4569 0.1875 0.099 Uiso 1 1 calc R . . C11 C 0.4093(3) 0.4245(2) 0.10457(18) 0.0568(6) Uani 1 1 d . . . H11A H 0.4960 0.3756 0.0911 0.085 Uiso 1 1 calc R . . H11B H 0.4221 0.4700 0.1589 0.085 Uiso 1 1 calc R . . H11C H 0.3908 0.4875 0.0591 0.085 Uiso 1 1 calc R . . C12 C 0.2620(4) 0.2584(3) 0.02603(17) 0.0675(8) Uani 1 1 d . . . H12A H 0.3478 0.2078 0.0134 0.101 Uiso 1 1 calc R . . H12B H 0.2458 0.3213 -0.0197 0.101 Uiso 1 1 calc R . . H12C H 0.1797 0.2003 0.0302 0.101 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 0.02659(8) 0.02956(9) 0.03120(9) -0.00156(5) 0.00019(5) 0.00000(5) Cl1 0.0343(3) 0.0417(3) 0.0526(3) -0.0003(2) 0.0041(2) 0.0091(2) N1 0.0316(8) 0.0346(8) 0.0390(8) -0.0041(7) -0.0023(7) -0.0031(7) N2 0.0322(8) 0.0317(8) 0.0328(8) -0.0036(7) 0.0014(6) 0.0025(6) C1 0.0438(12) 0.0450(12) 0.0504(13) -0.0078(10) -0.0098(10) -0.0084(10) C2 0.0477(12) 0.0385(11) 0.0444(11) -0.0103(9) -0.0003(10) -0.0019(9) C3 0.0673(16) 0.0498(13) 0.0483(13) -0.0106(11) -0.0070(12) -0.0191(13) C4 0.0508(14) 0.0704(16) 0.0562(14) -0.0048(12) -0.0059(12) -0.0287(13) C5 0.0335(11) 0.0657(15) 0.0527(12) -0.0033(11) -0.0002(9) -0.0114(10) C6 0.0329(9) 0.0413(10) 0.0369(10) 0.0009(9) -0.0010(8) -0.0038(8) C7 0.0295(10) 0.0395(10) 0.0425(11) -0.0028(9) 0.0051(8) 0.0023(8) C8 0.0594(14) 0.0448(12) 0.0384(11) -0.0024(10) 0.0102(10) -0.0062(11) C9 0.0483(12) 0.0390(11) 0.0388(11) 0.0042(9) -0.0032(9) 0.0085(9) C10 0.0575(15) 0.0574(15) 0.0828(19) 0.0172(14) 0.0043(14) 0.0241(13) C11 0.0636(15) 0.0468(13) 0.0600(15) 0.0158(12) 0.0078(12) -0.0011(11) C12 0.105(3) 0.0576(15) 0.0393(12) 0.0060(12) -0.0193(14) 0.0031(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 C1 2.021(2) . ? Pd1 N2 2.1054(16) . ? Pd1 N1 2.1426(16) . ? Pd1 Cl1 2.3172(5) . ? N1 C6 1.335(3) . ? N1 C2 1.337(3) . ? N2 C7 1.492(2) . ? N2 C9 1.527(3) . ? N2 H2 0.9100 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.382(3) . ? C2 H2A 0.9300 . ? C3 C4 1.363(4) . ? C3 H3A 0.9300 . ? C4 C5 1.386(4) . ? C4 H4A 0.9300 . ? C5 C6 1.380(3) . ? C5 H5A 0.9300 . ? C6 C7 1.511(3) . ? C7 C8 1.532(3) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C11 1.510(4) . ? C9 C12 1.517(3) . ? C9 C10 1.530(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C1 Pd1 N2 95.14(8) . . ? C1 Pd1 N1 173.05(9) . . ? N2 Pd1 N1 79.75(7) . . ? C1 Pd1 Cl1 90.21(7) . . ? N2 Pd1 Cl1 174.64(5) . . ? N1 Pd1 Cl1 94.93(5) . . ? C6 N1 C2 118.93(18) . . ? C6 N1 Pd1 111.73(13) . . ? C2 N1 Pd1 129.32(15) . . ? C7 N2 C9 116.02(16) . . ? C7 N2 Pd1 103.76(11) . . ? C9 N2 Pd1 116.37(12) . . ? C7 N2 H2 106.7 . . ? C9 N2 H2 106.7 . . ? Pd1 N2 H2 106.7 . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.1(2) . . ? N1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H5A 120.9 . . ? C4 C5 H5A 120.9 . . ? N1 C6 C5 122.2(2) . . ? N1 C6 C7 115.65(16) . . ? C5 C6 C7 122.10(19) . . ? N2 C7 C6 110.15(15) . . ? N2 C7 C8 109.27(18) . . ? C6 C7 C8 109.76(18) . . ? N2 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C11 C9 C12 109.6(2) . . ? C11 C9 N2 107.11(18) . . ? C12 C9 N2 111.11(17) . . ? C11 C9 C10 108.2(2) . . ? C12 C9 C10 110.3(2) . . ? N2 C9 C10 110.50(19) . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.498 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.233 # Attachment 'cis-6a.cif' data_ic10905 _database_code_depnum_ccdc_archive 'CCDC 736879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Cl N2 Pd' _chemical_formula_weight 369.17 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4240(3) _cell_length_b 9.6334(3) _cell_length_c 10.8944(4) _cell_angle_alpha 110.5170(19) _cell_angle_beta 105.1710(19) _cell_angle_gamma 98.641(2) _cell_volume 770.00(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 32654 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 1.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.520 _exptl_absorpt_correction_T_max 0.767 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5884 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3469 _reflns_number_gt 2990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0491P)^2^+0.5828P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3469 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.017 _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 1.01887(3) 0.45277(3) 0.83731(3) 0.04322(15) Uani 1 1 d . . . Cl1 Cl 1.27619(12) 0.64041(11) 0.95874(11) 0.0577(3) Uani 1 1 d . . . N1 N 1.1045(4) 0.2651(3) 0.8671(3) 0.0441(6) Uani 1 1 d . . . N2 N 0.7843(4) 0.2813(3) 0.7338(3) 0.0455(7) Uani 1 1 d D . . H2 H 0.755(6) 0.327(5) 0.809(3) 0.066(14) Uiso 1 1 d D . . C1 C 0.9129(5) 0.6110(4) 0.7912(5) 0.0578(10) Uani 1 1 d . . . H1A H 0.7944 0.5644 0.7359 0.087 Uiso 1 1 calc R . . H1B H 0.9708 0.6495 0.7398 0.087 Uiso 1 1 calc R . . H1C H 0.9231 0.6944 0.8759 0.087 Uiso 1 1 calc R . . C2 C 1.2635(5) 0.2686(4) 0.9372(4) 0.0487(8) Uani 1 1 d . . . H2A H 1.3496 0.3595 0.9739 0.058 Uiso 1 1 calc R . . C3 C 1.3034(5) 0.1430(5) 0.9563(4) 0.0538(9) Uani 1 1 d . . . H3A H 1.4152 0.1477 1.0025 0.065 Uiso 1 1 calc R . . C4 C 1.1747(5) 0.0097(5) 0.9060(5) 0.0569(10) Uani 1 1 d . . . H4A H 1.1980 -0.0762 0.9198 0.068 Uiso 1 1 calc R . . C5 C 1.0108(5) 0.0053(4) 0.8349(4) 0.0534(9) Uani 1 1 d . . . H5A H 0.9222 -0.0835 0.8001 0.064 Uiso 1 1 calc R . . C6 C 0.9803(5) 0.1345(4) 0.8160(4) 0.0481(8) Uani 1 1 d . . . C7 C 0.8049(5) 0.1291(4) 0.7316(5) 0.0668(12) Uani 1 1 d . . . H7A H 0.7790 0.0580 0.6358 0.080 Uiso 1 1 calc R . . H7B H 0.7223 0.0890 0.7667 0.080 Uiso 1 1 calc R . . C8 C 0.6795(5) 0.2710(4) 0.5994(4) 0.0484(8) Uani 1 1 d . . . C9 C 0.5176(5) 0.2945(5) 0.5846(4) 0.0532(9) Uani 1 1 d . . . C10 C 0.4224(5) 0.2939(5) 0.4588(5) 0.0620(11) Uani 1 1 d . . . H10A H 0.3142 0.3095 0.4473 0.074 Uiso 1 1 calc R . . C11 C 0.4858(7) 0.2707(6) 0.3527(5) 0.0729(13) Uani 1 1 d . . . H11A H 0.4213 0.2720 0.2698 0.087 Uiso 1 1 calc R . . C12 C 0.6436(7) 0.2456(7) 0.3674(5) 0.0842(15) Uani 1 1 d . . . H12A H 0.6839 0.2278 0.2930 0.101 Uiso 1 1 calc R . . C13 C 0.7455(6) 0.2461(6) 0.4907(5) 0.0703(12) Uani 1 1 d . . . C14 C 0.4430(6) 0.3207(8) 0.6990(6) 0.0897(18) Uani 1 1 d . . . H14A H 0.5231 0.3182 0.7787 0.134 Uiso 1 1 calc R . . H14B H 0.3393 0.2414 0.6674 0.134 Uiso 1 1 calc R . . H14C H 0.4188 0.4191 0.7243 0.134 Uiso 1 1 calc R . . C15 C 0.9230(8) 0.2255(9) 0.5054(6) 0.112(2) Uani 1 1 d . . . H15A H 0.9756 0.2284 0.5961 0.168 Uiso 1 1 calc R . . H15B H 0.9902 0.3068 0.4940 0.168 Uiso 1 1 calc R . . H15C H 0.9160 0.1282 0.4354 0.168 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 0.03976(19) 0.03882(19) 0.0473(2) 0.01983(13) 0.00737(12) 0.00766(11) Cl1 0.0451(5) 0.0511(5) 0.0665(6) 0.0267(5) 0.0060(4) 0.0002(4) N1 0.0418(15) 0.0382(14) 0.0488(17) 0.0175(13) 0.0109(13) 0.0098(12) N2 0.0370(15) 0.0432(15) 0.0492(18) 0.0196(14) 0.0042(13) 0.0078(12) C1 0.054(2) 0.047(2) 0.070(3) 0.028(2) 0.0106(19) 0.0146(17) C2 0.0422(18) 0.0497(19) 0.054(2) 0.0248(17) 0.0119(16) 0.0112(15) C3 0.045(2) 0.061(2) 0.060(2) 0.031(2) 0.0144(17) 0.0198(17) C4 0.059(2) 0.052(2) 0.063(3) 0.0300(19) 0.0150(19) 0.0207(18) C5 0.053(2) 0.0444(18) 0.064(3) 0.0261(18) 0.0156(18) 0.0121(16) C6 0.0473(19) 0.0421(18) 0.051(2) 0.0197(16) 0.0112(16) 0.0095(15) C7 0.053(2) 0.045(2) 0.082(3) 0.028(2) -0.005(2) 0.0051(17) C8 0.0443(19) 0.0429(18) 0.046(2) 0.0155(16) 0.0027(15) 0.0084(15) C9 0.0436(19) 0.056(2) 0.053(2) 0.0233(18) 0.0071(16) 0.0111(16) C10 0.047(2) 0.072(3) 0.056(3) 0.025(2) 0.0014(18) 0.0174(19) C11 0.073(3) 0.084(3) 0.048(3) 0.025(2) 0.004(2) 0.020(2) C12 0.078(3) 0.120(4) 0.045(3) 0.021(3) 0.017(2) 0.036(3) C13 0.059(3) 0.088(3) 0.053(3) 0.017(2) 0.016(2) 0.026(2) C14 0.046(2) 0.157(6) 0.076(3) 0.055(4) 0.021(2) 0.035(3) C15 0.079(4) 0.179(7) 0.067(4) 0.025(4) 0.030(3) 0.055(4) _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 C1 2.021(4) . ? Pd1 N2 2.110(3) . ? Pd1 N1 2.139(3) . ? Pd1 Cl1 2.3156(9) . ? N1 C6 1.340(5) . ? N1 C2 1.346(5) . ? N2 C8 1.459(5) . ? N2 C7 1.495(5) . ? N2 H2 0.905(19) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.372(5) . ? C2 H2A 0.9300 . ? C3 C4 1.379(6) . ? C3 H3A 0.9300 . ? C4 C5 1.382(6) . ? C4 H4A 0.9300 . ? C5 C6 1.380(5) . ? C5 H5A 0.9300 . ? C6 C7 1.505(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.393(5) . ? C8 C13 1.398(6) . ? C9 C10 1.392(5) . ? C9 C14 1.500(7) . ? C10 C11 1.360(7) . ? C10 H10A 0.9300 . ? C11 C12 1.365(7) . ? C11 H11A 0.9300 . ? C12 C13 1.390(7) . ? C12 H12A 0.9300 . ? C13 C15 1.513(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C1 Pd1 N2 92.26(14) . . ? C1 Pd1 N1 173.16(14) . . ? N2 Pd1 N1 81.19(11) . . ? C1 Pd1 Cl1 88.68(12) . . ? N2 Pd1 Cl1 177.83(9) . . ? N1 Pd1 Cl1 97.93(8) . . ? C6 N1 C2 118.6(3) . . ? C6 N1 Pd1 114.2(2) . . ? C2 N1 Pd1 127.1(2) . . ? C8 N2 C7 113.1(3) . . ? C8 N2 Pd1 117.2(2) . . ? C7 N2 Pd1 111.6(2) . . ? C8 N2 H2 118(3) . . ? C7 N2 H2 106(3) . . ? Pd1 N2 H2 87(3) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.5(3) . . ? N1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C2 C3 C4 118.8(4) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 119.1(4) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? N1 C6 C5 121.9(3) . . ? N1 C6 C7 118.2(3) . . ? C5 C6 C7 119.8(3) . . ? N2 C7 C6 114.2(3) . . ? N2 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N2 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 121.2(4) . . ? C9 C8 N2 118.7(4) . . ? C13 C8 N2 120.0(4) . . ? C10 C9 C8 118.4(4) . . ? C10 C9 C14 119.1(4) . . ? C8 C9 C14 122.4(4) . . ? C11 C10 C9 120.9(4) . . ? C11 C10 H10A 119.6 . . ? C9 C10 H10A 119.6 . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C12 C13 121.6(5) . . ? C11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C12 C13 C8 117.6(4) . . ? C12 C13 C15 120.1(5) . . ? C8 C13 C15 122.3(4) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.643 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.084 # Attachment 'cis-6b.cif' data_ic11859 _database_code_depnum_ccdc_archive 'CCDC 736880' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H27 B F4 N4 Pd' _chemical_formula_weight 516.67 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' 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' 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 P2(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 11.71270(10) _cell_length_b 15.1903(2) _cell_length_c 13.7906(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.3550(8) _cell_angle_gamma 90.00 _cell_volume 2269.21(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 43029 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_T_max 0.849 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17211 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5135 _reflns_number_gt 4366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0782P)^2^+1.2511P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.040(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5135 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 0.76667(2) 0.140662(15) 0.063315(18) 0.04288(15) Uani 1 1 d . . . N1 N 0.6585(3) 0.07580(19) 0.1343(2) 0.0501(7) Uani 1 1 d . . . N2 N 0.7253(3) 0.24780(18) 0.1375(2) 0.0411(6) Uani 1 1 d . . . H2 H 0.673(4) 0.262(2) 0.101(3) 0.036(11) Uiso 1 1 d . . . N3 N 0.7973(3) 0.0356(2) -0.0112(3) 0.0571(8) Uani 1 1 d . . . C1 C 0.8633(4) 0.2165(3) 0.0009(3) 0.0594(9) Uani 1 1 d . . . H1A H 0.9052 0.1796 -0.0315 0.089 Uiso 1 1 calc R . . H1B H 0.9228 0.2508 0.0553 0.089 Uiso 1 1 calc R . . H1C H 0.8078 0.2552 -0.0507 0.089 Uiso 1 1 calc R . . C2 C 0.6177(4) -0.0086(3) 0.1182(4) 0.0631(10) Uani 1 1 d . . . H2A H 0.6447 -0.0451 0.0771 0.076 Uiso 1 1 calc R . . C3 C 0.5381(5) -0.0420(3) 0.1604(4) 0.0749(12) Uani 1 1 d . . . H3A H 0.5117 -0.1002 0.1483 0.090 Uiso 1 1 calc R . . C4 C 0.4977(5) 0.0118(3) 0.2207(4) 0.0739(12) Uani 1 1 d . . . H4A H 0.4439 -0.0096 0.2504 0.089 Uiso 1 1 calc R . . C5 C 0.5380(4) 0.0978(3) 0.2370(3) 0.0606(9) Uani 1 1 d . . . H5A H 0.5105 0.1354 0.2767 0.073 Uiso 1 1 calc R . . C6 C 0.6192(3) 0.1277(2) 0.1938(3) 0.0471(7) Uani 1 1 d . . . C7 C 0.6797(3) 0.2172(2) 0.2207(3) 0.0467(7) Uani 1 1 d . . . H7A H 0.7530 0.2098 0.2853 0.056 Uiso 1 1 calc R . . C8 C 0.6004(5) 0.2859(3) 0.2436(4) 0.0694(12) Uani 1 1 d . . . H8A H 0.5737 0.2645 0.2970 0.104 Uiso 1 1 calc R . . H8B H 0.5297 0.2979 0.1809 0.104 Uiso 1 1 calc R . . H8C H 0.6473 0.3389 0.2673 0.104 Uiso 1 1 calc R . . C9 C 0.8126(3) 0.3205(2) 0.1755(2) 0.0424(7) Uani 1 1 d . . . C10 C 0.9312(3) 0.3043(2) 0.2494(3) 0.0457(7) Uani 1 1 d . . . C11 C 1.0100(4) 0.3762(3) 0.2873(3) 0.0579(9) Uani 1 1 d . . . H11A H 1.0884 0.3672 0.3381 0.069 Uiso 1 1 calc R . . C12 C 0.9743(4) 0.4597(3) 0.2513(3) 0.0648(10) Uani 1 1 d . . . H12A H 1.0283 0.5066 0.2775 0.078 Uiso 1 1 calc R . . C13 C 0.8586(4) 0.4743(2) 0.1765(3) 0.0621(10) Uani 1 1 d . . . H13A H 0.8351 0.5313 0.1526 0.075 Uiso 1 1 calc R . . C14 C 0.7760(3) 0.4052(2) 0.1359(3) 0.0504(8) Uani 1 1 d . . . C15 C 0.9807(4) 0.2138(3) 0.2896(3) 0.0558(9) Uani 1 1 d . . . H15A H 0.9177 0.1706 0.2580 0.084 Uiso 1 1 calc R . . H15B H 1.0051 0.2122 0.3644 0.084 Uiso 1 1 calc R . . H15C H 1.0509 0.2013 0.2721 0.084 Uiso 1 1 calc R . . C16 C 0.6523(4) 0.4243(3) 0.0511(4) 0.0676(11) Uani 1 1 d . . . H16A H 0.6061 0.3707 0.0306 0.101 Uiso 1 1 calc R . . H16B H 0.6639 0.4495 -0.0083 0.101 Uiso 1 1 calc R . . H16C H 0.6079 0.4651 0.0770 0.101 Uiso 1 1 calc R . . C17 C 0.8091(4) -0.0265(3) -0.0519(3) 0.0610(9) Uani 1 1 d . . . C18 C 0.8230(6) -0.1077(4) -0.1019(5) 0.0908(16) Uani 1 1 d . . . H18A H 0.9092 -0.1193 -0.0843 0.136 Uiso 1 1 calc R . . H18B H 0.7824 -0.1019 -0.1766 0.136 Uiso 1 1 calc R . . H18C H 0.7867 -0.1554 -0.0781 0.136 Uiso 1 1 calc R . . B1 B 0.3616(5) 0.2331(3) 0.4215(5) 0.0689(13) Uani 1 1 d . . . F1 F 0.2971(4) 0.2931(3) 0.4500(5) 0.1512(18) Uani 1 1 d . . . F2 F 0.4843(3) 0.2545(2) 0.4549(3) 0.0992(10) Uani 1 1 d . . . F3 F 0.3133(6) 0.2385(6) 0.3186(4) 0.226(4) Uani 1 1 d . . . F4 F 0.3466(6) 0.1565(3) 0.4527(10) 0.249(5) Uani 1 1 d . . . N4 N 0.8432(5) 0.4526(4) -0.1028(4) 0.0976(15) Uani 1 1 d . . . C19 C 0.8427(6) 0.5196(6) -0.0976(5) 0.0902(16) Uani 1 1 d . . . C20 C 0.8455(8) 0.6189(5) -0.0894(7) 0.123(3) Uani 1 1 d . . . H20A H 0.9296 0.6389 -0.0639 0.184 Uiso 1 1 calc R . . H20B H 0.8078 0.6370 -0.0418 0.184 Uiso 1 1 calc R . . H20C H 0.8010 0.6439 -0.1573 0.184 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 0.0490(2) 0.0378(2) 0.0428(2) -0.00236(8) 0.01845(13) 0.00213(9) N1 0.0575(17) 0.0375(14) 0.0566(17) -0.0016(12) 0.0231(14) -0.0045(12) N2 0.0436(15) 0.0354(14) 0.0427(15) 0.0010(11) 0.0147(13) 0.0017(12) N3 0.067(2) 0.0468(17) 0.0605(18) -0.0049(14) 0.0269(16) 0.0032(14) C1 0.072(2) 0.059(2) 0.060(2) 0.0009(17) 0.039(2) -0.0024(18) C2 0.082(3) 0.042(2) 0.070(2) -0.0059(17) 0.035(2) -0.0075(18) C3 0.088(3) 0.049(2) 0.096(3) -0.002(2) 0.044(3) -0.019(2) C4 0.082(3) 0.064(3) 0.088(3) 0.004(2) 0.046(3) -0.018(2) C5 0.067(2) 0.058(2) 0.065(2) -0.0002(18) 0.035(2) -0.0062(18) C6 0.0482(18) 0.0420(17) 0.0495(18) 0.0003(13) 0.0167(15) -0.0003(13) C7 0.0545(19) 0.0397(17) 0.0513(18) -0.0029(13) 0.0259(15) -0.0019(14) C8 0.087(3) 0.046(2) 0.098(3) -0.006(2) 0.060(3) 0.0027(19) C9 0.0498(17) 0.0369(16) 0.0425(16) -0.0018(12) 0.0196(14) -0.0014(13) C10 0.0501(18) 0.0428(17) 0.0450(17) -0.0006(13) 0.0188(14) -0.0007(14) C11 0.053(2) 0.060(2) 0.054(2) -0.0060(17) 0.0134(17) -0.0100(17) C12 0.072(3) 0.049(2) 0.067(2) -0.0089(18) 0.019(2) -0.0184(18) C13 0.078(3) 0.0365(18) 0.070(2) -0.0002(16) 0.026(2) -0.0068(17) C14 0.058(2) 0.0373(17) 0.0540(19) 0.0009(14) 0.0196(16) 0.0011(14) C15 0.0527(19) 0.052(2) 0.056(2) 0.0036(16) 0.0133(16) 0.0077(16) C16 0.071(3) 0.044(2) 0.075(3) 0.0129(18) 0.014(2) 0.0070(18) C17 0.068(2) 0.054(2) 0.065(2) -0.0060(18) 0.030(2) 0.0038(18) C18 0.117(4) 0.067(3) 0.098(4) -0.022(3) 0.052(3) 0.010(3) B1 0.053(2) 0.059(3) 0.090(4) -0.002(2) 0.022(2) -0.002(2) F1 0.115(3) 0.133(4) 0.217(5) -0.032(3) 0.076(3) 0.022(3) F2 0.0549(14) 0.090(2) 0.131(3) 0.0255(18) 0.0102(16) -0.0056(14) F3 0.127(4) 0.426(12) 0.109(4) -0.072(6) 0.028(3) -0.067(5) F4 0.125(4) 0.088(3) 0.529(16) 0.077(5) 0.119(7) -0.009(3) N4 0.108(4) 0.091(4) 0.095(3) -0.015(3) 0.039(3) -0.010(3) C19 0.080(3) 0.121(5) 0.073(3) -0.017(3) 0.033(3) -0.015(4) C20 0.151(7) 0.109(5) 0.127(6) -0.044(5) 0.074(6) -0.042(5) _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 N3 2.003(3) . ? Pd1 C1 2.022(4) . ? Pd1 N2 2.075(3) . ? Pd1 N1 2.116(3) . ? N1 C6 1.338(5) . ? N1 C2 1.357(5) . ? N2 C9 1.460(4) . ? N2 C7 1.512(4) . ? N2 H2 0.67(4) . ? N3 C17 1.133(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.370(6) . ? C2 H2A 0.9300 . ? C3 C4 1.372(7) . ? C3 H3A 0.9300 . ? C4 C5 1.379(6) . ? C4 H4A 0.9300 . ? C5 C6 1.378(5) . ? C5 H5A 0.9300 . ? C6 C7 1.513(5) . ? C7 C8 1.508(5) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.397(5) . ? C9 C14 1.399(5) . ? C10 C11 1.397(5) . ? C10 C15 1.512(5) . ? C11 C12 1.367(6) . ? C11 H11A 0.9300 . ? C12 C13 1.373(6) . ? C12 H12A 0.9300 . ? C13 C14 1.393(5) . ? C13 H13A 0.9300 . ? C14 C16 1.504(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.452(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? B1 F4 1.275(7) . ? B1 F3 1.314(8) . ? B1 F1 1.336(7) . ? B1 F2 1.370(6) . ? N4 C19 1.021(8) . ? C19 C20 1.512(10) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 N3 Pd1 C1 89.84(15) . . ? N3 Pd1 N2 177.04(13) . . ? C1 Pd1 N2 92.07(14) . . ? N3 Pd1 N1 97.00(12) . . ? C1 Pd1 N1 173.01(14) . . ? N2 Pd1 N1 81.03(11) . . ? C6 N1 C2 118.4(3) . . ? C6 N1 Pd1 114.5(2) . . ? C2 N1 Pd1 126.8(3) . . ? C9 N2 C7 111.2(3) . . ? C9 N2 Pd1 120.5(2) . . ? C7 N2 Pd1 110.4(2) . . ? C9 N2 H2 111(3) . . ? C7 N2 H2 100(3) . . ? Pd1 N2 H2 101(3) . . ? C17 N3 Pd1 175.7(4) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.3(4) . . ? N1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C2 C3 C4 119.0(4) . . ? C2 C3 H3A 120.5 . . ? C4 C3 H3A 120.5 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 119.4(4) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? N1 C6 C5 121.7(3) . . ? N1 C6 C7 116.2(3) . . ? C5 C6 C7 121.7(3) . . ? C8 C7 N2 111.7(3) . . ? C8 C7 C6 113.9(3) . . ? N2 C7 C6 110.9(3) . . ? C8 C7 H7A 106.6 . . ? N2 C7 H7A 106.6 . . ? C6 C7 H7A 106.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 121.2(3) . . ? C10 C9 N2 119.6(3) . . ? C14 C9 N2 119.1(3) . . ? C11 C10 C9 117.8(3) . . ? C11 C10 C15 117.8(3) . . ? C9 C10 C15 124.3(3) . . ? C12 C11 C10 121.5(4) . . ? C12 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? C11 C12 C13 120.0(4) . . ? C11 C12 H12A 120.0 . . ? C13 C12 H12A 120.0 . . ? C12 C13 C14 121.1(4) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? C13 C14 C9 118.2(3) . . ? C13 C14 C16 118.9(3) . . ? C9 C14 C16 122.9(3) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 C18 178.3(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F4 B1 F3 111.3(7) . . ? F4 B1 F1 110.9(6) . . ? F3 B1 F1 102.4(6) . . ? F4 B1 F2 111.4(5) . . ? F3 B1 F2 108.3(5) . . ? F1 B1 F2 112.1(5) . . ? N4 C19 C20 178.5(8) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.112 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.186 # Attachment 'cis-6b.cif' data_ic11437 _database_code_depnum_ccdc_archive 'CCDC 736881' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 Cl N2 Pd' _chemical_formula_weight 383.20 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.32470(10) _cell_length_b 9.65630(10) _cell_length_c 10.88200(10) _cell_angle_alpha 108.6800(10) _cell_angle_beta 101.9830(10) _cell_angle_gamma 93.6160(10) _cell_volume 802.657(15) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 27539 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.773 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6809 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3657 _reflns_number_gt 3528 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0409P)^2^+0.4050P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0197(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3657 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 0.033296(15) 0.456781(13) 0.339106(12) 0.02963(8) Uani 1 1 d . . . Cl1 Cl 0.26347(7) 0.63202(6) 0.45617(6) 0.04584(13) Uani 1 1 d . . . N1 N 0.1354(2) 0.27064(18) 0.37103(16) 0.0344(3) Uani 1 1 d . . . N2 N -0.1723(2) 0.29319(18) 0.23519(16) 0.0320(3) Uani 1 1 d . . . C1 C -0.0888(3) 0.6176(2) 0.2956(2) 0.0421(4) Uani 1 1 d . . . H1A H -0.1989 0.5755 0.2425 0.063 Uiso 1 1 calc R . . H1B H -0.0303 0.6610 0.2466 0.063 Uiso 1 1 calc R . . H1C H -0.0948 0.6922 0.3771 0.063 Uiso 1 1 calc R . . C2 C 0.2864(3) 0.2730(2) 0.4454(2) 0.0415(4) Uani 1 1 d . . . H2A H 0.3596 0.3607 0.4804 0.050 Uiso 1 1 calc R . . C3 C 0.3374(3) 0.1498(3) 0.4720(3) 0.0518(5) Uani 1 1 d . . . H3A H 0.4436 0.1539 0.5224 0.062 Uiso 1 1 calc R . . C4 C 0.2283(4) 0.0216(3) 0.4227(3) 0.0595(6) Uani 1 1 d . . . H4A H 0.2587 -0.0621 0.4411 0.071 Uiso 1 1 calc R . . C5 C 0.0720(3) 0.0176(2) 0.3451(3) 0.0528(5) Uani 1 1 d . . . H5A H -0.0034 -0.0687 0.3107 0.063 Uiso 1 1 calc R . . C6 C 0.0296(3) 0.1443(2) 0.31955(19) 0.0372(4) Uani 1 1 d . . . C7 C -0.1314(3) 0.1407(2) 0.2230(2) 0.0433(4) Uani 1 1 d . . . H7A H -0.1139 0.0970 0.1330 0.052 Uiso 1 1 calc R . . C8 C -0.2777(4) 0.0446(3) 0.2306(4) 0.0739(9) Uani 1 1 d . . . H8A H -0.3748 0.0476 0.1665 0.111 Uiso 1 1 calc R . . H8B H -0.2965 0.0807 0.3187 0.111 Uiso 1 1 calc R . . H8C H -0.2544 -0.0552 0.2113 0.111 Uiso 1 1 calc R . . C9 C -0.2687(2) 0.2983(2) 0.10899(18) 0.0349(4) Uani 1 1 d . . . C10 C -0.1905(3) 0.2881(3) 0.0052(2) 0.0443(5) Uani 1 1 d . . . C11 C -0.2853(3) 0.2927(3) -0.1151(2) 0.0538(6) Uani 1 1 d . . . H11A H -0.2359 0.2853 -0.1857 0.065 Uiso 1 1 calc R . . C12 C -0.4508(3) 0.3081(3) -0.1308(2) 0.0555(6) Uani 1 1 d . . . H12A H -0.5125 0.3099 -0.2118 0.067 Uiso 1 1 calc R . . C13 C -0.5246(3) 0.3209(3) -0.0271(2) 0.0495(5) Uani 1 1 d . . . H13A H -0.6362 0.3324 -0.0385 0.059 Uiso 1 1 calc R . . C14 C -0.4360(2) 0.3169(2) 0.0954(2) 0.0405(4) Uani 1 1 d . . . C15 C -0.0074(3) 0.2790(4) 0.0180(3) 0.0635(7) Uani 1 1 d . . . H15A H 0.0425 0.2781 0.1055 0.095 Uiso 1 1 calc R . . H15B H 0.0444 0.3629 0.0046 0.095 Uiso 1 1 calc R . . H15C H 0.0070 0.1901 -0.0481 0.095 Uiso 1 1 calc R . . C16 C -0.5225(3) 0.3351(4) 0.2065(3) 0.0612(7) Uani 1 1 d . . . H16A H -0.6359 0.3470 0.1763 0.092 Uiso 1 1 calc R . . H16B H -0.4681 0.4207 0.2815 0.092 Uiso 1 1 calc R . . H16C H -0.5189 0.2493 0.2328 0.092 Uiso 1 1 calc R . . H2 H -0.223(3) 0.316(3) 0.289(3) 0.037(6) Uiso 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 Pd1 0.03092(10) 0.02810(10) 0.02870(9) 0.01122(6) 0.00336(6) 0.00039(6) Cl1 0.0421(3) 0.0415(3) 0.0461(3) 0.0147(2) -0.0010(2) -0.0098(2) N1 0.0372(8) 0.0326(8) 0.0333(7) 0.0130(6) 0.0052(6) 0.0049(6) N2 0.0315(8) 0.0337(8) 0.0290(7) 0.0112(6) 0.0037(6) 0.0007(6) C1 0.0455(11) 0.0370(10) 0.0451(11) 0.0186(8) 0.0062(9) 0.0076(8) C2 0.0369(10) 0.0465(11) 0.0413(10) 0.0171(9) 0.0057(8) 0.0072(8) C3 0.0485(12) 0.0576(14) 0.0536(13) 0.0258(11) 0.0071(10) 0.0201(10) C4 0.0734(17) 0.0494(13) 0.0640(15) 0.0310(12) 0.0113(13) 0.0243(12) C5 0.0651(15) 0.0345(10) 0.0570(13) 0.0190(10) 0.0061(11) 0.0052(10) C6 0.0448(10) 0.0309(9) 0.0346(9) 0.0117(7) 0.0065(8) 0.0040(7) C7 0.0504(12) 0.0312(9) 0.0389(10) 0.0075(8) -0.0007(9) -0.0010(8) C8 0.0582(16) 0.0435(13) 0.106(2) 0.0299(15) -0.0090(16) -0.0170(11) C9 0.0336(9) 0.0366(9) 0.0291(8) 0.0096(7) 0.0003(7) -0.0016(7) C10 0.0439(11) 0.0531(12) 0.0332(9) 0.0126(9) 0.0073(8) 0.0043(9) C11 0.0646(15) 0.0631(14) 0.0301(10) 0.0148(10) 0.0070(10) 0.0030(11) C12 0.0639(15) 0.0559(14) 0.0345(10) 0.0132(10) -0.0090(10) 0.0030(11) C13 0.0382(10) 0.0529(12) 0.0458(11) 0.0132(10) -0.0077(9) 0.0016(9) C14 0.0331(9) 0.0447(10) 0.0376(9) 0.0118(8) 0.0007(8) -0.0009(8) C15 0.0486(13) 0.102(2) 0.0441(12) 0.0250(13) 0.0180(10) 0.0144(13) C16 0.0362(11) 0.092(2) 0.0577(14) 0.0276(14) 0.0129(10) 0.0092(12) _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 C1 2.034(2) . ? Pd1 N2 2.1013(16) . ? Pd1 N1 2.1317(16) . ? Pd1 Cl1 2.3140(5) . ? N1 C2 1.341(3) . ? N1 C6 1.341(3) . ? N2 C9 1.457(2) . ? N2 C7 1.503(3) . ? C2 C3 1.382(3) . ? C3 C4 1.370(4) . ? C4 C5 1.387(4) . ? C5 C6 1.389(3) . ? C6 C7 1.512(3) . ? C7 C8 1.516(3) . ? C9 C10 1.397(3) . ? C9 C14 1.399(3) . ? C10 C11 1.396(3) . ? C10 C15 1.512(3) . ? C11 C12 1.376(4) . ? C12 C13 1.369(4) . ? C13 C14 1.397(3) . ? C14 C16 1.501(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 C1 Pd1 N2 92.63(8) . . ? C1 Pd1 N1 173.24(7) . . ? N2 Pd1 N1 80.62(6) . . ? C1 Pd1 Cl1 89.04(7) . . ? N2 Pd1 Cl1 178.30(4) . . ? N1 Pd1 Cl1 97.71(5) . . ? C2 N1 C6 119.13(17) . . ? C2 N1 Pd1 126.01(14) . . ? C6 N1 Pd1 114.60(13) . . ? C9 N2 C7 111.70(15) . . ? C9 N2 Pd1 117.64(12) . . ? C7 N2 Pd1 112.34(12) . . ? N1 C2 C3 122.4(2) . . ? C4 C3 C2 118.7(2) . . ? C3 C4 C5 119.4(2) . . ? C4 C5 C6 119.1(2) . . ? N1 C6 C5 121.20(19) . . ? N1 C6 C7 117.68(16) . . ? C5 C6 C7 120.91(19) . . ? N2 C7 C6 111.92(16) . . ? N2 C7 C8 110.7(2) . . ? C6 C7 C8 114.3(2) . . ? C10 C9 C14 121.43(18) . . ? C10 C9 N2 119.11(17) . . ? C14 C9 N2 119.44(17) . . ? C11 C10 C9 118.1(2) . . ? C11 C10 C15 118.3(2) . . ? C9 C10 C15 123.53(19) . . ? C12 C11 C10 121.1(2) . . ? C13 C12 C11 120.0(2) . . ? C12 C13 C14 121.4(2) . . ? C13 C14 C9 117.9(2) . . ? C13 C14 C16 119.0(2) . . ? C9 C14 C16 123.10(19) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.404 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.058 # Attachment 'cis-7b.cif' data_ic10704 _database_code_depnum_ccdc_archive 'CCDC 736882' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 Cl N2 Pd' _chemical_formula_weight 439.30 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.5827(4) _cell_length_b 9.6041(2) _cell_length_c 17.4202(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.3690(11) _cell_angle_gamma 90.00 _cell_volume 4105.71(13) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 24291 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 1.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.857 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12879 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4667 _reflns_number_gt 3560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0350P)^2^+4.2986P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00100(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4667 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.186068(7) 0.256836(18) 0.447298(11) 0.03533(9) Uani 1 1 d . . . Cl1 Cl 0.24027(3) 0.35886(8) 0.35891(4) 0.0539(2) Uani 1 1 d . . . N1 N 0.19934(8) 0.0475(2) 0.41565(12) 0.0391(5) Uani 1 1 d . . . N2 N 0.13839(8) 0.1572(2) 0.52691(13) 0.0334(5) Uani 1 1 d . . . C1 C 0.16614(10) 0.4537(2) 0.48600(16) 0.0391(6) Uani 1 1 d . . . H1A H 0.1418 0.4452 0.5269 0.059 Uiso 1 1 calc R . . H1B H 0.1487 0.5058 0.4444 0.059 Uiso 1 1 calc R . . H1C H 0.1987 0.5010 0.5046 0.059 Uiso 1 1 calc R . . C2 C 0.23156(11) 0.0048(3) 0.36050(16) 0.0492(7) Uani 1 1 d . . . H2A H 0.2479 0.0712 0.3306 0.059 Uiso 1 1 calc R . . C3 C 0.24115(12) -0.1341(3) 0.34675(17) 0.0547(8) Uani 1 1 d . . . H3A H 0.2634 -0.1608 0.3080 0.066 Uiso 1 1 calc R . . C4 C 0.21749(13) -0.2318(3) 0.39075(18) 0.0543(8) Uani 1 1 d . . . H4A H 0.2237 -0.3261 0.3827 0.065 Uiso 1 1 calc R . . C5 C 0.18432(11) -0.1891(3) 0.44739(16) 0.0481(7) Uani 1 1 d . . . H5A H 0.1680 -0.2546 0.4780 0.058 Uiso 1 1 calc R . . C6 C 0.17536(10) -0.0489(3) 0.45842(14) 0.0364(6) Uani 1 1 d . . . C7 C 0.13565(10) 0.0013(2) 0.51601(15) 0.0376(6) Uani 1 1 d . . . H7A H 0.0990 -0.0198 0.4939 0.045 Uiso 1 1 calc R . . C8 C 0.14172(12) -0.0740(3) 0.59274(17) 0.0530(7) Uani 1 1 d . . . H8A H 0.1156 -0.0382 0.6265 0.079 Uiso 1 1 calc R . . H8B H 0.1778 -0.0595 0.6154 0.079 Uiso 1 1 calc R . . H8C H 0.1356 -0.1718 0.5849 0.079 Uiso 1 1 calc R . . C9 C 0.08537(10) 0.2194(2) 0.53944(15) 0.0354(5) Uani 1 1 d . . . C10 C 0.04629(10) 0.2244(3) 0.47736(16) 0.0398(6) Uani 1 1 d . . . C11 C -0.00426(12) 0.2836(3) 0.49017(19) 0.0519(7) Uani 1 1 d . . . H11A H -0.0309 0.2862 0.4501 0.062 Uiso 1 1 calc R . . C12 C -0.01569(12) 0.3379(3) 0.5601(2) 0.0606(8) Uani 1 1 d . . . H12A H -0.0497 0.3769 0.5672 0.073 Uiso 1 1 calc R . . C13 C 0.02343(11) 0.3343(3) 0.61984(18) 0.0537(7) Uani 1 1 d . . . H13A H 0.0155 0.3720 0.6671 0.064 Uiso 1 1 calc R . . C14 C 0.07470(10) 0.2757(3) 0.61155(16) 0.0418(6) Uani 1 1 d . . . C15 C 0.05621(11) 0.1741(3) 0.39650(15) 0.0447(6) Uani 1 1 d . . . H15A H 0.0928 0.1331 0.3977 0.054 Uiso 1 1 calc R . . C16 C 0.05471(14) 0.2925(4) 0.33937(18) 0.0635(9) Uani 1 1 d . . . H16A H 0.0806 0.3624 0.3564 0.095 Uiso 1 1 calc R . . H16B H 0.0188 0.3323 0.3354 0.095 Uiso 1 1 calc R . . H16C H 0.0638 0.2581 0.2900 0.095 Uiso 1 1 calc R . . C17 C 0.01529(13) 0.0604(4) 0.3699(2) 0.0687(9) Uani 1 1 d . . . H17A H 0.0224 0.0314 0.3188 0.103 Uiso 1 1 calc R . . H17B H -0.0211 0.0966 0.3704 0.103 Uiso 1 1 calc R . . H17C H 0.0190 -0.0179 0.4041 0.103 Uiso 1 1 calc R . . C18 C 0.11492(12) 0.2776(4) 0.68132(18) 0.0581(8) Uani 1 1 d . . . H18A H 0.1494 0.2380 0.6659 0.070 Uiso 1 1 calc R . . C19 C 0.12615(16) 0.4271(5) 0.7092(2) 0.0946(14) Uani 1 1 d . . . H19A H 0.1517 0.4255 0.7531 0.142 Uiso 1 1 calc R . . H19B H 0.0927 0.4692 0.7232 0.142 Uiso 1 1 calc R . . H19C H 0.1411 0.4801 0.6687 0.142 Uiso 1 1 calc R . . C20 C 0.09473(15) 0.1876(5) 0.74632(19) 0.0814(11) Uani 1 1 d . . . H20A H 0.0876 0.0949 0.7277 0.122 Uiso 1 1 calc R . . H20B H 0.0618 0.2268 0.7641 0.122 Uiso 1 1 calc R . . H20C H 0.1221 0.1847 0.7880 0.122 Uiso 1 1 calc R . . H2 H 0.1592(10) 0.167(3) 0.5623(14) 0.032(7) Uiso 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 Pd1 0.03257(13) 0.03050(13) 0.04368(14) 0.00182(8) 0.00876(8) -0.00184(8) Cl1 0.0502(4) 0.0549(4) 0.0583(4) 0.0125(4) 0.0173(3) -0.0067(3) N1 0.0369(11) 0.0348(11) 0.0465(12) -0.0005(10) 0.0089(9) 0.0023(9) N2 0.0292(11) 0.0309(11) 0.0401(12) -0.0019(9) 0.0027(9) -0.0003(9) C1 0.0416(14) 0.0175(11) 0.0596(17) -0.0016(11) 0.0144(12) -0.0066(10) C2 0.0484(16) 0.0520(17) 0.0486(16) -0.0019(13) 0.0150(13) 0.0056(13) C3 0.0546(18) 0.0581(19) 0.0527(17) -0.0117(15) 0.0137(14) 0.0113(15) C4 0.063(2) 0.0390(16) 0.0608(19) -0.0113(14) 0.0006(15) 0.0098(14) C5 0.0540(18) 0.0343(14) 0.0565(18) -0.0003(13) 0.0069(14) 0.0032(12) C6 0.0350(13) 0.0317(13) 0.0423(14) -0.0017(11) 0.0009(10) 0.0020(10) C7 0.0337(13) 0.0286(12) 0.0508(15) 0.0030(11) 0.0056(11) -0.0036(10) C8 0.0576(18) 0.0432(16) 0.0597(18) 0.0120(14) 0.0169(14) -0.0005(14) C9 0.0292(12) 0.0308(12) 0.0470(15) 0.0009(11) 0.0083(10) -0.0010(10) C10 0.0362(14) 0.0341(13) 0.0494(15) 0.0032(11) 0.0048(11) -0.0009(11) C11 0.0362(15) 0.0534(17) 0.066(2) 0.0032(15) -0.0003(13) 0.0081(13) C12 0.0424(17) 0.0574(19) 0.083(2) -0.0027(17) 0.0139(16) 0.0155(15) C13 0.0466(16) 0.0533(18) 0.0631(19) -0.0122(15) 0.0190(14) 0.0040(14) C14 0.0355(14) 0.0423(14) 0.0483(15) -0.0050(12) 0.0101(11) -0.0013(11) C15 0.0396(14) 0.0469(16) 0.0474(16) 0.0018(13) 0.0010(12) -0.0015(12) C16 0.070(2) 0.072(2) 0.0482(18) 0.0103(17) -0.0046(15) -0.0068(18) C17 0.061(2) 0.068(2) 0.077(2) -0.0135(19) 0.0011(17) -0.0115(17) C18 0.0427(16) 0.082(2) 0.0509(17) -0.0193(16) 0.0115(13) -0.0036(15) C19 0.083(3) 0.110(3) 0.092(3) -0.048(3) 0.012(2) -0.026(2) C20 0.074(2) 0.118(3) 0.052(2) 0.001(2) 0.0027(17) -0.001(2) _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 C1 2.075(2) . ? Pd1 N2 2.098(2) . ? Pd1 N1 2.115(2) . ? Pd1 Cl1 2.3124(7) . ? N1 C2 1.345(3) . ? N1 C6 1.346(3) . ? N2 C9 1.462(3) . ? N2 C7 1.511(3) . ? N2 H2 0.78(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.378(4) . ? C2 H2A 0.9300 . ? C3 C4 1.363(4) . ? C3 H3A 0.9300 . ? C4 C5 1.379(4) . ? C4 H4A 0.9300 . ? C5 C6 1.380(4) . ? C5 H5A 0.9300 . ? C6 C7 1.519(3) . ? C7 C8 1.519(4) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.404(4) . ? C9 C14 1.406(4) . ? C10 C11 1.396(4) . ? C10 C15 1.522(4) . ? C11 C12 1.370(4) . ? C11 H11A 0.9300 . ? C12 C13 1.375(4) . ? C12 H12A 0.9300 . ? C13 C14 1.396(4) . ? C13 H13A 0.9300 . ? C14 C18 1.521(4) . ? C15 C16 1.511(4) . ? C15 C17 1.538(4) . ? C15 H15A 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C20 1.530(5) . ? C18 C19 1.536(5) . ? C18 H18A 0.9800 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C1 Pd1 N2 92.80(9) . . ? C1 Pd1 N1 173.46(8) . . ? N2 Pd1 N1 80.77(8) . . ? C1 Pd1 Cl1 89.23(7) . . ? N2 Pd1 Cl1 177.87(6) . . ? N1 Pd1 Cl1 97.21(6) . . ? C2 N1 C6 118.8(2) . . ? C2 N1 Pd1 125.63(19) . . ? C6 N1 Pd1 115.49(16) . . ? C9 N2 C7 112.97(19) . . ? C9 N2 Pd1 116.74(15) . . ? C7 N2 Pd1 113.04(15) . . ? C9 N2 H2 112.4(19) . . ? C7 N2 H2 104(2) . . ? Pd1 N2 H2 95.9(19) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.2(3) . . ? N1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? N1 C6 C5 121.0(2) . . ? N1 C6 C7 117.8(2) . . ? C5 C6 C7 121.1(2) . . ? N2 C7 C6 111.84(19) . . ? N2 C7 C8 111.1(2) . . ? C6 C7 C8 113.4(2) . . ? N2 C7 H7A 106.7 . . ? C6 C7 H7A 106.7 . . ? C8 C7 H7A 106.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 121.3(2) . . ? C10 C9 N2 118.3(2) . . ? C14 C9 N2 120.3(2) . . ? C11 C10 C9 117.7(3) . . ? C11 C10 C15 118.0(2) . . ? C9 C10 C15 124.2(2) . . ? C12 C11 C10 121.9(3) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C11 C12 C13 119.5(3) . . ? C11 C12 H12A 120.2 . . ? C13 C12 H12A 120.2 . . ? C12 C13 C14 121.8(3) . . ? C12 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C9 117.7(3) . . ? C13 C14 C18 117.4(3) . . ? C9 C14 C18 124.9(2) . . ? C16 C15 C10 111.8(3) . . ? C16 C15 C17 110.3(2) . . ? C10 C15 C17 111.5(2) . . ? C16 C15 H15A 107.7 . . ? C10 C15 H15A 107.7 . . ? C17 C15 H15A 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 C20 111.1(3) . . ? C14 C18 C19 111.1(3) . . ? C20 C18 C19 110.7(3) . . ? C14 C18 H18A 107.9 . . ? C20 C18 H18A 107.9 . . ? C19 C18 H18A 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.493 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.066 # Attachment 'trans-3b.cif' data_ic10648 _database_code_depnum_ccdc_archive 'CCDC 736883' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 Cl N2 Pd' _chemical_formula_weight 321.13 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9040(2) _cell_length_b 8.4760(2) _cell_length_c 10.5230(2) _cell_angle_alpha 89.2210(10) _cell_angle_beta 86.4850(10) _cell_angle_gamma 66.2490(10) _cell_volume 644.01(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 15621 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 1.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.733 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4803 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2863 _reflns_number_gt 2714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0286P)^2^+0.3678P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.033(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2863 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.004 _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 0.56605(2) 0.06721(2) 0.213332(15) 0.03436(11) Uani 1 1 d . . . Cl1 Cl 0.72851(11) -0.16561(10) 0.33832(7) 0.05756(19) Uani 1 1 d . . . N1 N 0.4162(3) 0.2780(3) 0.10906(19) 0.0348(4) Uani 1 1 d . . . N2 N 0.3089(3) 0.1846(3) 0.33673(19) 0.0368(4) Uani 1 1 d . . . H2 H 0.318(4) 0.165(4) 0.422(3) 0.039(7) Uiso 1 1 d . . . C1 C 0.7938(3) -0.0137(3) 0.0867(2) 0.0412(5) Uani 1 1 d . . . H1A H 0.7697 0.0633 0.0158 0.062 Uiso 1 1 calc R . . H1B H 0.8193 -0.1280 0.0568 0.062 Uiso 1 1 calc R . . H1C H 0.8988 -0.0141 0.1282 0.062 Uiso 1 1 calc R . . C2 C 0.4354(4) 0.2986(3) -0.0167(2) 0.0439(6) Uani 1 1 d . . . H2A H 0.5284 0.2116 -0.0644 0.053 Uiso 1 1 calc R . . C3 C 0.3224(4) 0.4437(4) -0.0775(3) 0.0519(7) Uani 1 1 d . . . H3A H 0.3395 0.4550 -0.1649 0.062 Uiso 1 1 calc R . . C4 C 0.1838(4) 0.5721(4) -0.0077(3) 0.0535(7) Uani 1 1 d . . . H4A H 0.1066 0.6720 -0.0470 0.064 Uiso 1 1 calc R . . C5 C 0.1608(4) 0.5506(3) 0.1217(3) 0.0493(6) Uani 1 1 d . . . H5A H 0.0666 0.6352 0.1704 0.059 Uiso 1 1 calc R . . C6 C 0.2787(3) 0.4029(3) 0.1775(2) 0.0371(5) Uani 1 1 d . . . C7 C 0.2637(4) 0.3699(3) 0.3193(2) 0.0400(5) Uani 1 1 d . . . H7A H 0.1363 0.4364 0.3527 0.048 Uiso 1 1 calc R . . C8 C 0.3950(4) 0.4228(4) 0.3910(3) 0.0520(7) Uani 1 1 d . . . H8A H 0.3828 0.4009 0.4801 0.078 Uiso 1 1 calc R . . H8B H 0.3646 0.5434 0.3789 0.078 Uiso 1 1 calc R . . H8C H 0.5201 0.3574 0.3590 0.078 Uiso 1 1 calc R . . C9 C 0.1613(4) 0.1277(4) 0.3015(2) 0.0458(6) Uani 1 1 d . . . H9A H 0.1517 0.1395 0.2091 0.055 Uiso 1 1 calc R . . C10 C 0.2234(5) -0.0628(4) 0.3323(4) 0.0631(8) Uani 1 1 d . . . H10A H 0.3435 -0.1266 0.2913 0.095 Uiso 1 1 calc R . . H10B H 0.1364 -0.1043 0.3022 0.095 Uiso 1 1 calc R . . H10C H 0.2296 -0.0777 0.4227 0.095 Uiso 1 1 calc R . . C11 C -0.0294(4) 0.2343(5) 0.3648(3) 0.0653(8) Uani 1 1 d . . . H11B H -0.0651 0.3535 0.3435 0.098 Uiso 1 1 calc R . . H11C H -0.0250 0.2219 0.4555 0.098 Uiso 1 1 calc R . . H11A H -0.1182 0.1947 0.3352 0.098 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 0.03600(13) 0.03188(13) 0.03140(13) 0.00063(7) 0.00169(7) -0.01025(8) Cl1 0.0636(4) 0.0521(4) 0.0415(3) 0.0102(3) -0.0031(3) -0.0074(3) N1 0.0361(10) 0.0348(9) 0.0333(10) 0.0009(8) 0.0008(8) -0.0145(8) N2 0.0385(10) 0.0412(11) 0.0300(10) 0.0002(8) 0.0018(8) -0.0158(9) C1 0.0338(12) 0.0405(12) 0.0388(12) 0.0027(10) 0.0110(10) -0.0060(10) C2 0.0490(14) 0.0442(13) 0.0373(12) 0.0026(10) 0.0004(10) -0.0179(12) C3 0.0612(17) 0.0589(17) 0.0405(13) 0.0139(12) -0.0119(12) -0.0284(15) C4 0.0541(16) 0.0447(15) 0.0584(17) 0.0164(13) -0.0171(13) -0.0149(13) C5 0.0454(14) 0.0387(13) 0.0577(16) 0.0018(11) -0.0056(12) -0.0104(11) C6 0.0340(11) 0.0341(11) 0.0429(12) -0.0005(9) -0.0024(9) -0.0135(9) C7 0.0392(12) 0.0384(12) 0.0376(12) -0.0063(10) 0.0057(10) -0.0115(10) C8 0.0635(18) 0.0521(15) 0.0445(14) -0.0084(12) -0.0024(13) -0.0274(14) C9 0.0473(14) 0.0595(16) 0.0377(12) 0.0028(11) 0.0001(11) -0.0293(13) C10 0.070(2) 0.0598(18) 0.072(2) 0.0029(15) 0.0026(16) -0.0403(17) C11 0.0436(16) 0.084(2) 0.072(2) 0.0018(18) 0.0023(14) -0.0303(16) _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 2.049(2) . ? Pd1 C1 2.055(2) . ? Pd1 N2 2.211(2) . ? Pd1 Cl1 2.3170(7) . ? N1 C2 1.339(3) . ? N1 C6 1.349(3) . ? N2 C7 1.474(3) . ? N2 C9 1.498(3) . ? N2 H2 0.91(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.373(4) . ? C3 H3A 0.9300 . ? C4 C5 1.382(4) . ? C4 H4A 0.9300 . ? C5 C6 1.374(4) . ? C5 H5A 0.9300 . ? C6 C7 1.521(3) . ? C7 C8 1.525(4) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.523(4) . ? C9 C11 1.526(4) . ? C9 H9A 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11A 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 N1 Pd1 C1 94.32(9) . . ? N1 Pd1 N2 78.78(8) . . ? C1 Pd1 N2 172.91(8) . . ? N1 Pd1 Cl1 177.75(6) . . ? C1 Pd1 Cl1 87.72(7) . . ? N2 Pd1 Cl1 99.15(6) . . ? C2 N1 C6 118.7(2) . . ? C2 N1 Pd1 127.25(18) . . ? C6 N1 Pd1 113.99(16) . . ? C7 N2 C9 114.8(2) . . ? C7 N2 Pd1 101.37(14) . . ? C9 N2 Pd1 112.65(15) . . ? C7 N2 H2 106.8(17) . . ? C9 N2 H2 104.1(17) . . ? Pd1 N2 H2 117.4(18) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.3(3) . . ? N1 C2 H2A 118.9 . . ? C3 C2 H2A 118.9 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? N1 C6 C5 121.6(2) . . ? N1 C6 C7 115.8(2) . . ? C5 C6 C7 122.6(2) . . ? N2 C7 C6 108.30(19) . . ? N2 C7 C8 110.1(2) . . ? C6 C7 C8 111.1(2) . . ? N2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 108.4(2) . . ? N2 C9 C11 113.8(2) . . ? C10 C9 C11 111.3(3) . . ? N2 C9 H9A 107.7 . . ? C10 C9 H9A 107.7 . . ? C11 C9 H9A 107.7 . . ? 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 . . ? C9 C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.467 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.063 # Attachment 'trans-4a.cif' data_ic11265 _database_code_depnum_ccdc_archive 'CCDC 736884' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 B F4 N3 Pd' _chemical_formula_weight 413.55 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' 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 P2(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 7.63290(10) _cell_length_b 12.1420(3) _cell_length_c 20.1943(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.2060(13) _cell_angle_gamma 90.00 _cell_volume 1847.47(7) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 16990 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 1.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.723 _exptl_absorpt_correction_T_max 0.812 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10140 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4044 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0918P)^2^+1.1853P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0241(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4044 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1441 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.004 _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 0.80844(3) 0.46471(2) 0.062230(13) 0.04216(17) Uani 1 1 d . . . N1 N 0.9186(4) 0.6112(2) 0.09541(15) 0.0455(7) Uani 1 1 d . . . N2 N 0.9163(4) 0.4171(3) 0.16590(16) 0.0479(7) Uani 1 1 d . . . H2 H 0.966(6) 0.347(4) 0.158(2) 0.048(11) Uiso 1 1 d . . . N3 N 0.7233(5) 0.3155(3) 0.03073(19) 0.0621(9) Uani 1 1 d . . . C1 C 0.7185(6) 0.5209(4) -0.0313(2) 0.0598(11) Uani 1 1 d . . . H1A H 0.6550 0.4633 -0.0574 0.090 Uiso 1 1 calc R . . H1B H 0.8172 0.5438 -0.0521 0.090 Uiso 1 1 calc R . . H1C H 0.6407 0.5824 -0.0288 0.090 Uiso 1 1 calc R . . C2 C 0.8897(7) 0.7106(3) 0.0651(2) 0.0588(10) Uani 1 1 d . . . H2A H 0.8094 0.7163 0.0255 0.071 Uiso 1 1 calc R . . C3 C 0.9783(8) 0.8040(4) 0.0924(3) 0.0720(13) Uani 1 1 d . . . H3A H 0.9559 0.8719 0.0714 0.086 Uiso 1 1 calc R . . C4 C 1.0992(8) 0.7961(4) 0.1505(3) 0.0732(14) Uani 1 1 d . . . H4A H 1.1617 0.8580 0.1682 0.088 Uiso 1 1 calc R . . C5 C 1.1268(7) 0.6979(4) 0.1818(2) 0.0646(11) Uani 1 1 d . . . H5A H 1.2055 0.6924 0.2219 0.078 Uiso 1 1 calc R . . C6 C 1.0370(5) 0.6048(3) 0.15381(18) 0.0476(8) Uani 1 1 d . . . C7 C 1.0722(6) 0.4923(4) 0.1845(2) 0.0502(9) Uani 1 1 d . . . H7A H 1.1754 0.4606 0.1693 0.060 Uiso 1 1 calc R . . H7B H 1.0980 0.4992 0.2329 0.060 Uiso 1 1 calc R . . C8 C 0.7815(7) 0.4090(4) 0.2150(2) 0.0639(11) Uani 1 1 d . . . C9 C 0.7027(10) 0.5226(5) 0.2246(4) 0.0879(19) Uani 1 1 d . . . H9A H 0.7959 0.5723 0.2428 0.132 Uiso 1 1 calc R . . H9B H 0.6182 0.5169 0.2549 0.132 Uiso 1 1 calc R . . H9C H 0.6446 0.5499 0.1821 0.132 Uiso 1 1 calc R . . C10 C 0.8790(9) 0.3640(6) 0.2818(3) 0.0935(19) Uani 1 1 d . . . H10A H 0.9278 0.2929 0.2746 0.140 Uiso 1 1 calc R . . H10B H 0.7972 0.3574 0.3131 0.140 Uiso 1 1 calc R . . H10C H 0.9731 0.4134 0.2995 0.140 Uiso 1 1 calc R . . C11 C 0.6333(8) 0.3285(5) 0.1860(3) 0.0865(17) Uani 1 1 d . . . H11A H 0.6838 0.2575 0.1800 0.130 Uiso 1 1 calc R . . H11B H 0.5746 0.3555 0.1435 0.130 Uiso 1 1 calc R . . H11C H 0.5490 0.3223 0.2163 0.130 Uiso 1 1 calc R . . C12 C 0.6855(7) 0.2295(5) 0.0161(3) 0.0779(14) Uani 1 1 d . . . C13 C 0.6327(13) 0.1140(5) 0.0006(5) 0.132(3) Uani 1 1 d . . . H13A H 0.6059 0.0788 0.0403 0.198 Uiso 1 1 calc R . . H13B H 0.7282 0.0757 -0.0150 0.198 Uiso 1 1 calc R . . H13C H 0.5296 0.1126 -0.0336 0.198 Uiso 1 1 calc R . . B1 B 0.1743(9) 0.1288(4) 0.1185(3) 0.0651(13) Uani 1 1 d . . . F1 F 0.2719(15) 0.0621(5) 0.1566(3) 0.229(5) Uani 1 1 d . . . F2 F 0.0285(15) 0.0836(7) 0.0844(6) 0.275(6) Uani 1 1 d . . . F3 F 0.243(2) 0.1487(11) 0.0681(4) 0.306(7) Uani 1 1 d . . . F4 F 0.1482(10) 0.2234(4) 0.1442(4) 0.185(3) 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 Pd1 0.0423(2) 0.0449(2) 0.0390(2) -0.00275(10) 0.00559(13) -0.00096(10) N1 0.0507(17) 0.0430(15) 0.0436(16) 0.0011(13) 0.0101(13) -0.0014(13) N2 0.0558(19) 0.0427(17) 0.0449(17) 0.0024(13) 0.0071(14) 0.0004(15) N3 0.067(2) 0.055(2) 0.064(2) -0.0110(17) 0.0073(18) -0.0084(18) C1 0.052(2) 0.082(3) 0.044(2) 0.007(2) 0.0041(18) 0.001(2) C2 0.069(3) 0.050(2) 0.060(2) 0.0063(18) 0.016(2) 0.002(2) C3 0.097(4) 0.045(2) 0.080(3) 0.008(2) 0.031(3) -0.003(2) C4 0.093(4) 0.054(3) 0.075(3) -0.016(2) 0.022(3) -0.020(2) C5 0.076(3) 0.063(3) 0.055(2) -0.013(2) 0.013(2) -0.016(2) C6 0.055(2) 0.050(2) 0.0398(18) -0.0033(15) 0.0131(16) -0.0043(17) C7 0.054(2) 0.057(2) 0.0381(19) 0.0005(17) 0.0025(16) -0.0003(19) C8 0.067(3) 0.075(3) 0.050(2) 0.010(2) 0.011(2) -0.008(2) C9 0.097(5) 0.090(4) 0.088(4) 0.003(3) 0.051(4) 0.009(3) C10 0.100(4) 0.127(5) 0.053(3) 0.032(3) 0.009(3) -0.028(4) C11 0.078(3) 0.106(4) 0.076(3) 0.024(3) 0.011(3) -0.036(3) C12 0.076(3) 0.067(3) 0.094(4) -0.021(3) 0.022(3) -0.017(3) C13 0.150(7) 0.067(4) 0.178(9) -0.045(5) 0.026(6) -0.043(4) B1 0.093(4) 0.050(3) 0.051(3) 0.005(2) 0.006(3) 0.002(3) F1 0.401(13) 0.113(3) 0.126(4) 0.009(3) -0.099(6) 0.078(6) F2 0.264(10) 0.146(5) 0.345(13) -0.028(7) -0.165(10) -0.024(7) F3 0.454(18) 0.336(14) 0.154(7) 0.089(8) 0.126(9) 0.098(15) F4 0.223(6) 0.100(3) 0.208(6) -0.063(4) -0.034(5) 0.068(4) _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 N3 1.994(4) . ? Pd1 C1 2.022(4) . ? Pd1 N1 2.034(3) . ? Pd1 N2 2.201(3) . ? N1 C2 1.356(5) . ? N1 C6 1.368(5) . ? N2 C7 1.500(5) . ? N2 C8 1.542(6) . ? N2 H2 0.96(4) . ? N3 C12 1.111(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.389(7) . ? C2 H2A 0.9300 . ? C3 C4 1.376(8) . ? C3 H3A 0.9300 . ? C4 C5 1.349(7) . ? C4 H4A 0.9300 . ? C5 C6 1.395(6) . ? C5 H5A 0.9300 . ? C6 C7 1.506(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.528(8) . ? C8 C10 1.533(7) . ? C8 C11 1.538(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.479(8) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? B1 F3 1.241(10) . ? B1 F1 1.273(7) . ? B1 F4 1.288(7) . ? B1 F2 1.330(10) . ? 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 N3 Pd1 C1 87.94(18) . . ? N3 Pd1 N1 174.68(14) . . ? C1 Pd1 N1 94.21(17) . . ? N3 Pd1 N2 96.77(14) . . ? C1 Pd1 N2 175.25(16) . . ? N1 Pd1 N2 81.05(12) . . ? C2 N1 C6 118.5(3) . . ? C2 N1 Pd1 127.0(3) . . ? C6 N1 Pd1 114.6(2) . . ? C7 N2 C8 117.5(3) . . ? C7 N2 Pd1 103.8(2) . . ? C8 N2 Pd1 116.2(3) . . ? C7 N2 H2 105(3) . . ? C8 N2 H2 112(2) . . ? Pd1 N2 H2 100(2) . . ? C12 N3 Pd1 175.2(5) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.0(4) . . ? N1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 119.8(5) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? N1 C6 C5 121.1(4) . . ? N1 C6 C7 117.1(3) . . ? C5 C6 C7 121.7(4) . . ? N2 C7 C6 111.5(3) . . ? N2 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? N2 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C10 110.8(5) . . ? C9 C8 C11 110.0(5) . . ? C10 C8 C11 109.4(4) . . ? C9 C8 N2 109.9(4) . . ? C10 C8 N2 108.0(4) . . ? C11 C8 N2 108.7(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C13 176.6(7) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F3 B1 F1 109.6(9) . . ? F3 B1 F4 105.7(8) . . ? F1 B1 F4 115.9(6) . . ? F3 B1 F2 94.9(9) . . ? F1 B1 F2 114.2(7) . . ? F4 B1 F2 114.0(8) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.287 _refine_diff_density_min -0.804 _refine_diff_density_rms 0.251 # Attachment 'trans-4a.cif' data_ic11102 _database_code_depnum_ccdc_archive 'CCDC 736885' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 Cl N2 Pd' _chemical_formula_weight 321.13 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' 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 P2(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 9.1813(2) _cell_length_b 7.04020(10) _cell_length_c 20.5243(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.1410(9) _cell_angle_gamma 90.00 _cell_volume 1321.32(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 28940 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.792 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10638 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3021 _reflns_number_gt 2617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0203P)^2^+0.6637P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3021 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0517 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.475961(17) 0.01583(2) 0.134243(7) 0.03720(8) Uani 1 1 d . . . Cl1 Cl 0.67654(6) -0.07653(10) 0.08119(3) 0.05361(16) Uani 1 1 d . . . N1 N 0.29313(19) 0.0973(3) 0.17639(8) 0.0388(4) Uani 1 1 d . . . N2 N 0.3082(2) -0.1194(3) 0.06612(9) 0.0363(4) Uani 1 1 d . . . C1 C 0.6135(3) 0.1701(4) 0.19676(13) 0.0591(7) Uani 1 1 d . . . H1A H 0.5584 0.2328 0.2281 0.089 Uiso 1 1 calc R . . H1B H 0.6627 0.2633 0.1726 0.089 Uiso 1 1 calc R . . H1C H 0.6843 0.0872 0.2192 0.089 Uiso 1 1 calc R . . C2 C 0.2851(3) 0.1590(3) 0.23810(11) 0.0496(6) Uani 1 1 d . . . H2A H 0.3712 0.1710 0.2653 0.059 Uiso 1 1 calc R . . C3 C 0.1557(3) 0.2048(4) 0.26243(12) 0.0570(6) Uani 1 1 d . . . H3A H 0.1541 0.2482 0.3052 0.068 Uiso 1 1 calc R . . C4 C 0.0284(3) 0.1856(4) 0.22260(12) 0.0573(6) Uani 1 1 d . . . H4A H -0.0609 0.2162 0.2380 0.069 Uiso 1 1 calc R . . C5 C 0.0340(2) 0.1204(4) 0.15940(11) 0.0476(5) Uani 1 1 d . . . H5A H -0.0515 0.1058 0.1319 0.057 Uiso 1 1 calc R . . C6 C 0.1678(2) 0.0773(3) 0.13751(10) 0.0375(5) Uani 1 1 d . . . C7 C 0.1842(2) 0.0117(3) 0.06886(10) 0.0407(5) Uani 1 1 d . . . H7A H 0.0950 -0.0515 0.0517 0.049 Uiso 1 1 calc R . . H7B H 0.1987 0.1211 0.0415 0.049 Uiso 1 1 calc R . . C8 C 0.2710(3) -0.3281(3) 0.06791(11) 0.0460(5) Uani 1 1 d . . . C9 C 0.4144(4) -0.4356(4) 0.07978(16) 0.0709(8) Uani 1 1 d . . . H9A H 0.4628 -0.3988 0.1213 0.106 Uiso 1 1 calc R . . H9B H 0.4758 -0.4064 0.0457 0.106 Uiso 1 1 calc R . . H9C H 0.3952 -0.5697 0.0800 0.106 Uiso 1 1 calc R . . C10 C 0.1924(4) -0.3867(4) 0.00221(13) 0.0693(8) Uani 1 1 d . . . H10A H 0.1020 -0.3182 -0.0050 0.104 Uiso 1 1 calc R . . H10B H 0.1728 -0.5206 0.0025 0.104 Uiso 1 1 calc R . . H10C H 0.2532 -0.3580 -0.0322 0.104 Uiso 1 1 calc R . . C11 C 0.1764(4) -0.3668(4) 0.12366(14) 0.0711(8) Uani 1 1 d . . . H11A H 0.0858 -0.2987 0.1161 0.107 Uiso 1 1 calc R . . H11B H 0.2269 -0.3256 0.1642 0.107 Uiso 1 1 calc R . . H11C H 0.1567 -0.5005 0.1259 0.107 Uiso 1 1 calc R . . H2 H 0.340(2) -0.105(3) 0.0333(10) 0.032(6) Uiso 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 Pd1 0.03172(11) 0.04234(12) 0.03685(11) 0.00037(7) -0.00074(7) -0.00142(7) Cl1 0.0405(3) 0.0773(4) 0.0438(3) 0.0069(3) 0.0084(2) 0.0029(3) N1 0.0349(9) 0.0418(10) 0.0390(9) -0.0030(8) -0.0005(7) 0.0003(8) N2 0.0381(10) 0.0407(10) 0.0306(9) 0.0008(7) 0.0050(8) -0.0052(8) C1 0.0375(13) 0.0704(18) 0.0676(16) -0.0234(14) -0.0056(12) -0.0063(12) C2 0.0490(14) 0.0563(14) 0.0422(12) -0.0109(10) -0.0023(10) 0.0011(11) C3 0.0563(16) 0.0703(17) 0.0454(13) -0.0152(12) 0.0098(11) 0.0006(13) C4 0.0438(14) 0.0691(17) 0.0609(15) -0.0096(13) 0.0159(12) -0.0007(13) C5 0.0343(12) 0.0546(14) 0.0536(13) -0.0009(11) 0.0024(10) -0.0046(10) C6 0.0365(11) 0.0348(11) 0.0407(11) 0.0018(9) 0.0011(9) -0.0018(9) C7 0.0385(12) 0.0451(12) 0.0373(11) 0.0036(9) -0.0038(9) -0.0025(9) C8 0.0558(15) 0.0384(12) 0.0439(12) -0.0007(9) 0.0046(10) -0.0077(11) C9 0.079(2) 0.0449(15) 0.088(2) -0.0059(14) -0.0001(17) 0.0065(15) C10 0.086(2) 0.0560(16) 0.0639(17) -0.0139(13) -0.0043(15) -0.0194(15) C11 0.095(2) 0.0502(16) 0.0720(18) 0.0121(13) 0.0268(16) -0.0142(15) _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 C1 2.032(2) . ? Pd1 N1 2.0384(17) . ? Pd1 N2 2.2020(17) . ? Pd1 Cl1 2.3150(6) . ? N1 C2 1.347(3) . ? N1 C6 1.348(3) . ? N2 C7 1.470(3) . ? N2 C8 1.510(3) . ? C2 C3 1.367(3) . ? C3 C4 1.372(3) . ? C4 C5 1.381(3) . ? C5 C6 1.379(3) . ? C6 C7 1.503(3) . ? C8 C9 1.519(4) . ? C8 C11 1.522(3) . ? C8 C10 1.528(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 C1 Pd1 N1 94.04(9) . . ? C1 Pd1 N2 172.64(9) . . ? N1 Pd1 N2 80.52(7) . . ? C1 Pd1 Cl1 88.37(8) . . ? N1 Pd1 Cl1 177.04(5) . . ? N2 Pd1 Cl1 96.93(5) . . ? C2 N1 C6 118.30(19) . . ? C2 N1 Pd1 127.33(16) . . ? C6 N1 Pd1 114.30(13) . . ? C7 N2 C8 115.62(18) . . ? C7 N2 Pd1 101.78(12) . . ? C8 N2 Pd1 123.52(14) . . ? N1 C2 C3 122.8(2) . . ? C2 C3 C4 118.7(2) . . ? C3 C4 C5 119.4(2) . . ? C6 C5 C4 119.2(2) . . ? N1 C6 C5 121.5(2) . . ? N1 C6 C7 115.78(18) . . ? C5 C6 C7 122.7(2) . . ? N2 C7 C6 111.84(17) . . ? N2 C8 C9 107.1(2) . . ? N2 C8 C11 109.74(19) . . ? C9 C8 C11 109.6(2) . . ? N2 C8 C10 109.33(19) . . ? C9 C8 C10 109.9(2) . . ? C11 C8 C10 111.1(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.369 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.055 # Attachment 'trans-4b.cif' data_ic12052 _database_code_depnum_ccdc_archive 'CCDC 736886' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 B F4 N3 Pd' _chemical_formula_weight 427.57 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' 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 P2(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 11.6589(2) _cell_length_b 7.3818(2) _cell_length_c 22.3551(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.5540(10) _cell_angle_gamma 90.00 _cell_volume 1891.41(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 34684 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.864 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Nonius KappaCCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13190 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4270 _reflns_number_gt 3081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1135P)^2^+1.0605P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4270 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1816 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.13964(3) 0.38892(5) 0.086125(17) 0.0601(2) Uani 1 1 d . . . F1 F 0.6786(9) 0.3554(18) 0.0958(4) 0.256(7) Uani 1 1 d . . . F2 F 0.5002(6) 0.3013(17) 0.0993(5) 0.255(5) Uani 1 1 d . . . F3 F 0.6151(10) 0.4127(15) 0.1743(5) 0.267(6) Uani 1 1 d . . . F4 F 0.6358(10) 0.1606(12) 0.1523(5) 0.243(5) Uani 1 1 d . . . N1 N 0.0645(3) 0.4681(6) 0.15701(19) 0.0616(9) Uani 1 1 d . . . N2 N 0.2855(3) 0.5371(6) 0.13934(17) 0.0574(9) Uani 1 1 d . . . H2B H 0.3511 0.4763 0.1346 0.069 Uiso 1 1 calc R . . N3 N 0.2241(4) 0.3016(7) 0.0215(2) 0.0767(12) Uani 1 1 d . . . C1 C -0.0023(5) 0.2481(9) 0.0449(3) 0.0907(18) Uani 1 1 d . . . H1A H -0.0015 0.2388 0.0021 0.136 Uiso 1 1 calc R . . H1B H -0.0719 0.3099 0.0508 0.136 Uiso 1 1 calc R . . H1C H -0.0008 0.1289 0.0622 0.136 Uiso 1 1 calc R . . C2 C -0.0510(4) 0.4751(8) 0.1588(3) 0.0739(14) Uani 1 1 d . . . H2A H -0.1046 0.4460 0.1240 0.089 Uiso 1 1 calc R . . C3 C -0.0906(5) 0.5238(9) 0.2102(3) 0.0861(18) Uani 1 1 d . . . H3A H -0.1703 0.5277 0.2103 0.103 Uiso 1 1 calc R . . C4 C -0.0126(7) 0.5664(9) 0.2613(4) 0.089(2) Uani 1 1 d . . . H4A H -0.0382 0.5971 0.2970 0.107 Uiso 1 1 calc R . . C5 C 0.1042(6) 0.5637(8) 0.2594(3) 0.0761(15) Uani 1 1 d . . . H5A H 0.1585 0.5954 0.2937 0.091 Uiso 1 1 calc R . . C6 C 0.1411(4) 0.5136(7) 0.2065(2) 0.0615(11) Uani 1 1 d . . . C7 C 0.2703(4) 0.5027(7) 0.2030(2) 0.0638(12) Uani 1 1 d . . . H7A H 0.3132 0.5946 0.2299 0.077 Uiso 1 1 calc R . . C8 C 0.3165(5) 0.3173(10) 0.2233(3) 0.0845(17) Uani 1 1 d . . . H8A H 0.3981 0.3111 0.2216 0.127 Uiso 1 1 calc R . . H8B H 0.2751 0.2270 0.1969 0.127 Uiso 1 1 calc R . . H8C H 0.3056 0.2959 0.2642 0.127 Uiso 1 1 calc R . . C9 C 0.3050(4) 0.7329(7) 0.1234(2) 0.0662(12) Uani 1 1 d . . . C10 C 0.3229(6) 0.7301(9) 0.0569(3) 0.0834(16) Uani 1 1 d . . . H10A H 0.2541 0.6832 0.0314 0.125 Uiso 1 1 calc R . . H10B H 0.3884 0.6545 0.0536 0.125 Uiso 1 1 calc R . . H10C H 0.3373 0.8510 0.0443 0.125 Uiso 1 1 calc R . . C11 C 0.1979(6) 0.8458(8) 0.1290(4) 0.0857(17) Uani 1 1 d . . . H11A H 0.1876 0.8469 0.1706 0.129 Uiso 1 1 calc R . . H11B H 0.1301 0.7941 0.1039 0.129 Uiso 1 1 calc R . . H11C H 0.2085 0.9676 0.1159 0.129 Uiso 1 1 calc R . . C12 C 0.4142(6) 0.8066(10) 0.1638(3) 0.0897(18) Uani 1 1 d . . . H12A H 0.4033 0.8080 0.2053 0.135 Uiso 1 1 calc R . . H12B H 0.4287 0.9276 0.1513 0.135 Uiso 1 1 calc R . . H12C H 0.4795 0.7308 0.1602 0.135 Uiso 1 1 calc R . . C13 C 0.2765(6) 0.2510(9) -0.0127(3) 0.0834(16) Uani 1 1 d . . . C14 C 0.3483(10) 0.1881(16) -0.0554(5) 0.141(3) Uani 1 1 d . . . H14A H 0.4292 0.2000 -0.0373 0.211 Uiso 1 1 calc R . . H14B H 0.3321 0.2595 -0.0919 0.211 Uiso 1 1 calc R . . H14C H 0.3310 0.0633 -0.0652 0.211 Uiso 1 1 calc R . . B1 B 0.6044(6) 0.3107(11) 0.1265(3) 0.0772(18) 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 Pd1 0.0535(3) 0.0623(3) 0.0604(3) -0.00632(16) -0.00047(17) 0.00176(15) F1 0.156(6) 0.46(2) 0.169(7) 0.011(8) 0.065(5) -0.104(8) F2 0.096(4) 0.360(12) 0.274(10) 0.087(10) -0.056(5) -0.004(6) F3 0.261(12) 0.289(12) 0.267(12) -0.139(9) 0.090(9) 0.010(8) F4 0.295(11) 0.153(6) 0.243(10) 0.064(6) -0.053(9) 0.035(7) N1 0.053(2) 0.056(2) 0.075(3) -0.004(2) 0.0081(18) 0.0008(18) N2 0.0488(19) 0.064(2) 0.058(2) -0.0007(18) 0.0057(16) -0.0009(17) N3 0.079(3) 0.076(3) 0.072(3) -0.010(2) 0.007(2) 0.004(2) C1 0.071(3) 0.091(4) 0.098(4) -0.024(3) -0.016(3) -0.006(3) C2 0.054(3) 0.068(3) 0.099(4) -0.005(3) 0.011(3) 0.000(2) C3 0.069(3) 0.073(4) 0.126(6) -0.010(4) 0.043(4) -0.004(3) C4 0.104(5) 0.069(3) 0.108(5) -0.013(3) 0.051(4) -0.008(3) C5 0.088(4) 0.071(3) 0.074(4) -0.016(3) 0.027(3) -0.014(3) C6 0.061(3) 0.059(3) 0.066(3) -0.002(2) 0.016(2) -0.005(2) C7 0.055(3) 0.074(3) 0.060(3) -0.005(2) 0.005(2) -0.009(2) C8 0.064(3) 0.104(5) 0.082(4) 0.024(3) 0.006(3) 0.007(3) C9 0.061(3) 0.065(3) 0.072(3) 0.000(2) 0.009(2) -0.009(2) C10 0.091(4) 0.089(4) 0.072(3) 0.012(3) 0.019(3) -0.011(3) C11 0.083(4) 0.067(3) 0.108(5) 0.008(3) 0.017(3) 0.005(3) C12 0.078(4) 0.093(4) 0.093(4) -0.005(4) 0.004(3) -0.025(3) C13 0.088(4) 0.085(4) 0.080(4) -0.006(3) 0.021(3) 0.006(3) C14 0.160(9) 0.153(8) 0.125(7) -0.015(7) 0.068(7) 0.027(8) B1 0.061(3) 0.089(5) 0.085(4) 0.015(4) 0.021(3) 0.015(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 Pd1 N3 1.998(5) . ? Pd1 C1 2.028(5) . ? Pd1 N1 2.032(4) . ? Pd1 N2 2.182(4) . ? F1 B1 1.244(10) . ? F2 B1 1.257(9) . ? F3 B1 1.294(11) . ? F4 B1 1.271(10) . ? N1 C6 1.332(6) . ? N1 C2 1.354(6) . ? N2 C7 1.489(6) . ? N2 C9 1.515(7) . ? N2 H2B 0.9100 . ? N3 C13 1.127(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.363(8) . ? C2 H2A 0.9300 . ? C3 C4 1.360(11) . ? C3 H3A 0.9300 . ? C4 C5 1.370(10) . ? C4 H4A 0.9300 . ? C5 C6 1.381(7) . ? C5 H5A 0.9300 . ? C6 C7 1.524(7) . ? C7 C8 1.509(8) . ? C7 H7A 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C12 1.519(8) . ? C9 C11 1.526(8) . ? C9 C10 1.539(8) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.456(11) . ? 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 N3 Pd1 C1 88.6(2) . . ? N3 Pd1 N1 175.21(18) . . ? C1 Pd1 N1 94.0(2) . . ? N3 Pd1 N2 96.78(17) . . ? C1 Pd1 N2 174.0(2) . . ? N1 Pd1 N2 80.50(15) . . ? C6 N1 C2 119.0(5) . . ? C6 N1 Pd1 113.6(3) . . ? C2 N1 Pd1 127.3(4) . . ? C7 N2 C9 115.9(4) . . ? C7 N2 Pd1 102.6(3) . . ? C9 N2 Pd1 119.1(3) . . ? C7 N2 H2B 106.1 . . ? C9 N2 H2B 106.1 . . ? Pd1 N2 H2B 106.1 . . ? C13 N3 Pd1 176.6(5) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.8(5) . . ? N1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C2 119.4(6) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.1(6) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C4 C5 C6 119.8(6) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? N1 C6 C5 120.8(5) . . ? N1 C6 C7 117.6(4) . . ? C5 C6 C7 121.6(5) . . ? N2 C7 C8 110.1(4) . . ? N2 C7 C6 109.4(4) . . ? C8 C7 C6 109.5(4) . . ? N2 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C12 110.4(5) . . ? N2 C9 C11 110.0(4) . . ? C12 C9 C11 111.4(5) . . ? N2 C9 C10 105.5(4) . . ? C12 C9 C10 109.4(5) . . ? C11 C9 C10 110.1(5) . . ? 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 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 177.7(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 . . ? F1 B1 F2 117.1(9) . . ? F1 B1 F4 108.0(10) . . ? F2 B1 F4 110.1(10) . . ? F1 B1 F3 109.2(10) . . ? F2 B1 F3 111.7(9) . . ? F4 B1 F3 99.1(9) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.010 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.184 # Attachment 'trans-5a.cif' data_ic10676 _database_code_depnum_ccdc_archive 'CCDC 736887' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 Cl N2 Pd' _chemical_formula_weight 341.12 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2253(2) _cell_length_b 9.1194(2) _cell_length_c 10.6977(2) _cell_angle_alpha 93.8870(10) _cell_angle_beta 110.9020(10) _cell_angle_gamma 113.4540(10) _cell_volume 666.77(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 14090 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 1.571 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_T_max 0.731 _exptl_absorpt_process_details ; mu_exptl_absorpt_correction_type 'multi-scan' lti-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5239 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3008 _reflns_number_gt 2731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0303P)^2^+0.4056P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3008 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.004 _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 0.38226(3) 0.41478(2) 0.199422(19) 0.04113(12) Uani 1 1 d . . . Cl1 Cl 0.47405(12) 0.26710(9) 0.35340(8) 0.05479(19) Uani 1 1 d . . . N1 N 0.3059(3) 0.5565(3) 0.0711(2) 0.0457(5) Uani 1 1 d . . . N2 N 0.5465(4) 0.6573(3) 0.3499(2) 0.0455(5) Uani 1 1 d . . . C1 C 0.2236(5) 0.2038(4) 0.0499(3) 0.0622(8) Uani 1 1 d . . . H1A H 0.1605 0.2259 -0.0360 0.093 Uiso 1 1 calc R . . H1B H 0.1268 0.1257 0.0735 0.093 Uiso 1 1 calc R . . H1C H 0.3079 0.1593 0.0409 0.093 Uiso 1 1 calc R . . C2 C 0.2301(5) 0.5190(4) -0.0670(3) 0.0608(8) Uani 1 1 d . . . H2A H 0.2055 0.4172 -0.1132 0.073 Uiso 1 1 calc R . . C3 C 0.1871(6) 0.6239(5) -0.1430(4) 0.0785(11) Uani 1 1 d . . . H3A H 0.1338 0.5936 -0.2389 0.094 Uiso 1 1 calc R . . C4 C 0.2243(7) 0.7752(5) -0.0748(4) 0.0850(12) Uani 1 1 d . . . H4A H 0.1942 0.8481 -0.1238 0.102 Uiso 1 1 calc R . . C5 C 0.3065(6) 0.8163(4) 0.0667(4) 0.0716(10) Uani 1 1 d . . . H5A H 0.3352 0.9189 0.1144 0.086 Uiso 1 1 calc R . . C6 C 0.3464(4) 0.7061(4) 0.1379(3) 0.0506(6) Uani 1 1 d . . . C7 C 0.4292(5) 0.7430(4) 0.2935(3) 0.0549(7) Uani 1 1 d . . . H7A H 0.5099 0.8608 0.3311 0.066 Uiso 1 1 calc R . . H7B H 0.3229 0.7098 0.3220 0.066 Uiso 1 1 calc R . . C8 C 0.7476(4) 0.7342(3) 0.3710(3) 0.0457(6) Uani 1 1 d . . . C9 C 0.8183(5) 0.8558(4) 0.3076(3) 0.0550(7) Uani 1 1 d . . . H9A H 0.7355 0.8920 0.2492 0.066 Uiso 1 1 calc R . . C10 C 1.0141(5) 0.9242(4) 0.3314(4) 0.0665(9) Uani 1 1 d . . . H10A H 1.0620 1.0067 0.2889 0.080 Uiso 1 1 calc R . . C11 C 1.1368(5) 0.8716(4) 0.4165(4) 0.0721(10) Uani 1 1 d . . . H11A H 1.2676 0.9180 0.4319 0.086 Uiso 1 1 calc R . . C12 C 1.0661(5) 0.7496(4) 0.4793(4) 0.0745(10) Uani 1 1 d . . . H12A H 1.1488 0.7129 0.5370 0.089 Uiso 1 1 calc R . . C13 C 0.8719(5) 0.6816(4) 0.4565(4) 0.0603(8) Uani 1 1 d . . . H13A H 0.8247 0.5994 0.4994 0.072 Uiso 1 1 calc R . . H2 H 0.552(5) 0.648(4) 0.427(4) 0.060(10) Uiso 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 Pd1 0.04483(16) 0.03764(14) 0.04051(15) 0.01010(8) 0.01837(10) 0.01780(10) Cl1 0.0641(4) 0.0524(4) 0.0503(4) 0.0228(3) 0.0246(3) 0.0266(3) N1 0.0487(13) 0.0437(12) 0.0446(12) 0.0104(10) 0.0184(10) 0.0221(10) N2 0.0533(14) 0.0444(12) 0.0391(12) 0.0092(10) 0.0221(11) 0.0200(11) C1 0.072(2) 0.0426(15) 0.0510(17) 0.0018(13) 0.0100(15) 0.0213(15) C2 0.071(2) 0.0613(18) 0.0501(17) 0.0155(14) 0.0208(15) 0.0338(17) C3 0.094(3) 0.085(3) 0.056(2) 0.0302(18) 0.0217(19) 0.047(2) C4 0.103(3) 0.082(3) 0.085(3) 0.045(2) 0.033(2) 0.059(2) C5 0.084(2) 0.0596(19) 0.081(3) 0.0235(17) 0.028(2) 0.0464(19) C6 0.0520(16) 0.0490(15) 0.0582(17) 0.0142(13) 0.0247(13) 0.0282(13) C7 0.0602(18) 0.0510(16) 0.0601(18) 0.0058(13) 0.0281(15) 0.0299(14) C8 0.0540(16) 0.0371(12) 0.0418(14) 0.0004(10) 0.0216(12) 0.0169(12) C9 0.0576(18) 0.0496(16) 0.0490(16) 0.0052(13) 0.0241(14) 0.0157(14) C10 0.066(2) 0.0567(18) 0.0592(19) -0.0035(15) 0.0334(17) 0.0083(16) C11 0.0496(18) 0.0581(19) 0.084(2) -0.0212(18) 0.0274(18) 0.0086(16) C12 0.056(2) 0.059(2) 0.091(3) -0.0042(18) 0.0132(18) 0.0287(17) C13 0.0567(18) 0.0464(16) 0.066(2) 0.0100(14) 0.0174(15) 0.0203(14) _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 C1 2.015(3) . ? Pd1 N1 2.055(2) . ? Pd1 N2 2.212(2) . ? Pd1 Cl1 2.3065(7) . ? N1 C2 1.339(4) . ? N1 C6 1.349(4) . ? N2 C8 1.438(4) . ? N2 C7 1.468(4) . ? N2 H2 0.82(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.367(5) . ? C2 H2A 0.9300 . ? C3 C4 1.378(6) . ? C3 H3A 0.9300 . ? C4 C5 1.370(5) . ? C4 H4A 0.9300 . ? C5 C6 1.373(4) . ? C5 H5A 0.9300 . ? C6 C7 1.510(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.377(4) . ? C8 C9 1.378(4) . ? C9 C10 1.391(5) . ? C9 H9A 0.9300 . ? C10 C11 1.367(6) . ? C10 H10A 0.9300 . ? C11 C12 1.376(6) . ? C11 H11A 0.9300 . ? C12 C13 1.381(5) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 N1 94.40(11) . . ? C1 Pd1 N2 174.96(11) . . ? N1 Pd1 N2 80.56(9) . . ? C1 Pd1 Cl1 88.57(9) . . ? N1 Pd1 Cl1 176.93(6) . . ? N2 Pd1 Cl1 96.47(7) . . ? C2 N1 C6 118.4(3) . . ? C2 N1 Pd1 127.5(2) . . ? C6 N1 Pd1 114.07(19) . . ? C8 N2 C7 117.6(2) . . ? C8 N2 Pd1 111.13(16) . . ? C7 N2 Pd1 103.04(17) . . ? C8 N2 H2 104(2) . . ? C7 N2 H2 109(2) . . ? Pd1 N2 H2 112(2) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.9(3) . . ? N1 C2 H2A 118.6 . . ? C3 C2 H2A 118.6 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? N1 C6 C5 121.1(3) . . ? N1 C6 C7 116.8(2) . . ? C5 C6 C7 122.0(3) . . ? N2 C7 C6 112.2(2) . . ? N2 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N2 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C13 C8 C9 119.4(3) . . ? C13 C8 N2 118.2(3) . . ? C9 C8 N2 122.4(3) . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C11 C12 C13 119.9(4) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C8 C13 C12 120.7(3) . . ? C8 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? 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 N2 H2 Cl1 0.82(3) 3.26(3) 3.371(2) 91(2) . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.392 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.062 # Attachment 'trans-5a.cif' data_ic11059 _database_code_depnum_ccdc_archive 'CCDC 736888' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 B F4 N3 Pd' _chemical_formula_weight 433.53 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' B B 0.0013 0.0007 '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' 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 P2(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 9.9543(2) _cell_length_b 9.4463(2) _cell_length_c 18.9653(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.2370(10) _cell_angle_gamma 90.00 _cell_volume 1742.81(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 18690 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.720 _exptl_absorpt_correction_T_max 0.784 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10796 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3966 _reflns_number_gt 3070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV)' _computing_cell_refinement 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_data_reduction 'HKL Denzo & Scalepack (Otwinowski & Minor)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0322P)^2^+0.6758P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3966 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.201887(19) 0.02930(2) 0.458474(10) 0.04126(9) Uani 1 1 d . . . N1 N 0.0339(2) 0.1395(2) 0.40900(11) 0.0435(5) Uani 1 1 d . . . N2 N 0.1692(2) -0.0679(3) 0.35162(12) 0.0425(5) Uani 1 1 d . . . H2 H 0.185(3) -0.145(3) 0.3562(13) 0.035(8) Uiso 1 1 d . . . N3 N 0.3531(2) -0.0987(3) 0.50627(12) 0.0534(6) Uani 1 1 d . . . C1 C 0.2242(3) 0.1354(4) 0.55196(15) 0.0660(9) Uani 1 1 d . . . H1A H 0.2654 0.0744 0.5911 0.099 Uiso 1 1 calc R . . H1B H 0.1358 0.1661 0.5586 0.099 Uiso 1 1 calc R . . H1C H 0.2822 0.2162 0.5509 0.099 Uiso 1 1 calc R . . C2 C -0.0169(3) 0.2581(3) 0.43282(15) 0.0547(7) Uani 1 1 d . . . H2A H 0.0308 0.2993 0.4754 0.066 Uiso 1 1 calc R . . C3 C -0.1363(3) 0.3207(4) 0.39676(18) 0.0641(8) Uani 1 1 d . . . H3A H -0.1695 0.4019 0.4150 0.077 Uiso 1 1 calc R . . C4 C -0.2054(3) 0.2618(4) 0.33384(17) 0.0632(8) Uani 1 1 d . . . H4A H -0.2870 0.3021 0.3090 0.076 Uiso 1 1 calc R . . C5 C -0.1539(3) 0.1427(3) 0.30728(15) 0.0557(7) Uani 1 1 d . . . H5A H -0.1989 0.1033 0.2637 0.067 Uiso 1 1 calc R . . C6 C -0.0347(3) 0.0823(3) 0.34608(13) 0.0436(6) Uani 1 1 d . . . C7 C 0.0207(3) -0.0529(3) 0.32281(15) 0.0497(7) Uani 1 1 d . . . H7A H -0.0269 -0.1320 0.3391 0.060 Uiso 1 1 calc R . . H7B H 0.0030 -0.0559 0.2705 0.060 Uiso 1 1 calc R . . C8 C 0.2598(3) -0.0080(3) 0.31007(13) 0.0403(6) Uani 1 1 d . . . C9 C 0.2173(3) 0.0942(3) 0.25895(16) 0.0582(8) Uani 1 1 d . . . H9A H 0.1279 0.1288 0.2510 0.070 Uiso 1 1 calc R . . C10 C 0.3085(4) 0.1460(4) 0.21908(18) 0.0713(9) Uani 1 1 d . . . H10A H 0.2795 0.2157 0.1846 0.086 Uiso 1 1 calc R . . C11 C 0.4393(3) 0.0965(4) 0.22959(17) 0.0647(8) Uani 1 1 d . . . H11A H 0.4989 0.1302 0.2018 0.078 Uiso 1 1 calc R . . C12 C 0.4822(3) -0.0035(3) 0.28155(17) 0.0581(8) Uani 1 1 d . . . H12A H 0.5720 -0.0368 0.2895 0.070 Uiso 1 1 calc R . . C13 C 0.3941(3) -0.0554(3) 0.32224(14) 0.0477(7) Uani 1 1 d . . . H13A H 0.4249 -0.1224 0.3579 0.057 Uiso 1 1 calc R . . C14 C 0.4264(3) -0.1824(3) 0.53360(15) 0.0541(7) Uani 1 1 d . . . C15 C 0.5196(3) -0.2913(4) 0.56946(19) 0.0769(10) Uani 1 1 d . . . H15A H 0.5458 -0.2704 0.6201 0.115 Uiso 1 1 calc R . . H15B H 0.6001 -0.2937 0.5491 0.115 Uiso 1 1 calc R . . H15C H 0.4746 -0.3816 0.5629 0.115 Uiso 1 1 calc R . . B1 B 0.7939(4) 0.0497(4) 0.1023(2) 0.0598(9) Uani 1 1 d . . . F1 F 0.6900(2) 0.1352(2) 0.11607(13) 0.0949(7) Uani 1 1 d . . . F2 F 0.7612(3) 0.0016(3) 0.03327(11) 0.0899(6) Uani 1 1 d . . . F3 F 0.9107(2) 0.1320(3) 0.11274(16) 0.1170(9) Uani 1 1 d . . . F4 F 0.8131(3) -0.0618(2) 0.14844(12) 0.0978(7) 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 Pd1 0.04278(13) 0.04548(15) 0.03483(13) 0.00445(8) 0.00663(8) 0.00060(9) N1 0.0420(12) 0.0448(13) 0.0437(12) 0.0029(10) 0.0091(9) 0.0002(10) N2 0.0474(13) 0.0380(15) 0.0423(12) 0.0029(10) 0.0101(9) 0.0014(11) N3 0.0530(14) 0.0600(16) 0.0455(13) 0.0058(12) 0.0065(10) 0.0057(13) C1 0.078(2) 0.078(2) 0.0399(16) -0.0081(15) 0.0062(14) 0.0065(18) C2 0.0582(17) 0.0518(19) 0.0534(17) 0.0028(13) 0.0104(13) 0.0059(14) C3 0.064(2) 0.058(2) 0.073(2) 0.0097(16) 0.0215(16) 0.0174(16) C4 0.0486(17) 0.079(2) 0.063(2) 0.0209(17) 0.0148(14) 0.0154(16) C5 0.0434(15) 0.078(2) 0.0453(15) 0.0088(14) 0.0075(12) 0.0001(15) C6 0.0384(13) 0.0528(16) 0.0410(14) 0.0058(12) 0.0113(10) -0.0040(12) C7 0.0441(15) 0.0573(19) 0.0472(15) -0.0050(12) 0.0086(12) -0.0078(13) C8 0.0442(14) 0.0393(15) 0.0374(13) -0.0015(10) 0.0088(10) -0.0022(11) C9 0.0522(17) 0.064(2) 0.0606(18) 0.0203(15) 0.0177(13) 0.0133(15) C10 0.077(2) 0.073(2) 0.067(2) 0.0304(17) 0.0209(17) 0.0066(18) C11 0.0594(19) 0.072(2) 0.067(2) 0.0102(17) 0.0235(15) -0.0099(17) C12 0.0415(16) 0.069(2) 0.063(2) 0.0010(15) 0.0109(13) -0.0053(14) C13 0.0447(15) 0.0498(18) 0.0462(15) 0.0040(12) 0.0046(11) 0.0004(12) C14 0.0507(16) 0.060(2) 0.0504(16) 0.0046(14) 0.0078(13) 0.0018(15) C15 0.068(2) 0.070(2) 0.089(2) 0.0173(19) 0.0066(18) 0.0183(18) B1 0.066(2) 0.050(2) 0.062(2) -0.0071(17) 0.0116(17) -0.0039(18) F1 0.0972(16) 0.0778(15) 0.1185(17) -0.0056(13) 0.0424(13) 0.0220(12) F2 0.1174(17) 0.0885(15) 0.0656(14) -0.0145(10) 0.0234(12) -0.0107(13) F3 0.0846(16) 0.0811(16) 0.179(3) -0.0224(16) 0.0138(15) -0.0257(13) F4 0.135(2) 0.0689(14) 0.0803(15) 0.0104(11) 0.0013(13) 0.0033(13) _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 N3 1.993(2) . ? Pd1 C1 2.007(3) . ? Pd1 N1 2.024(2) . ? Pd1 N2 2.185(2) . ? N1 C2 1.346(4) . ? N1 C6 1.355(3) . ? N2 C8 1.434(3) . ? N2 C7 1.470(3) . ? N2 H2 0.74(3) . ? N3 C14 1.125(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.373(4) . ? C2 H2A 0.9300 . ? C3 C4 1.363(4) . ? C3 H3A 0.9300 . ? C4 C5 1.376(4) . ? C4 H4A 0.9300 . ? C5 C6 1.380(4) . ? C5 H5A 0.9300 . ? C6 C7 1.495(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.370(4) . ? C8 C13 1.382(4) . ? C9 C10 1.387(4) . ? C9 H9A 0.9300 . ? C10 C11 1.358(4) . ? C10 H10A 0.9300 . ? C11 C12 1.366(4) . ? C11 H11A 0.9300 . ? C12 C13 1.375(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.454(4) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? B1 F4 1.356(4) . ? B1 F2 1.358(4) . ? B1 F3 1.378(4) . ? B1 F1 1.380(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Pd1 C1 88.25(11) . . ? N3 Pd1 N1 173.38(9) . . ? C1 Pd1 N1 94.52(11) . . ? N3 Pd1 N2 96.69(9) . . ? C1 Pd1 N2 174.59(12) . . ? N1 Pd1 N2 80.80(9) . . ? C2 N1 C6 118.2(2) . . ? C2 N1 Pd1 127.23(19) . . ? C6 N1 Pd1 114.57(18) . . ? C8 N2 C7 117.2(2) . . ? C8 N2 Pd1 110.86(17) . . ? C7 N2 Pd1 104.17(16) . . ? C8 N2 H2 108(2) . . ? C7 N2 H2 108(2) . . ? Pd1 N2 H2 108(2) . . ? C14 N3 Pd1 171.7(2) . . ? Pd1 C1 H1A 109.5 . . ? Pd1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Pd1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.6(3) . . ? N1 C2 H2A 118.7 . . ? C3 C2 H2A 118.7 . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? N1 C6 C5 121.4(3) . . ? N1 C6 C7 116.9(2) . . ? C5 C6 C7 121.7(2) . . ? N2 C7 C6 112.2(2) . . ? N2 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N2 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C13 119.3(2) . . ? C9 C8 N2 122.1(2) . . ? C13 C8 N2 118.6(2) . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 119.1(3) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C8 120.0(3) . . ? C12 C13 H13A 120.0 . . ? C8 C13 H13A 120.0 . . ? N3 C14 C15 179.2(3) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? F4 B1 F2 109.6(3) . . ? F4 B1 F3 110.2(3) . . ? F2 B1 F3 110.5(3) . . ? F4 B1 F1 109.9(3) . . ? F2 B1 F1 110.0(3) . . ? F3 B1 F1 106.6(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.574 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.063