# Electronic Supplementary Material (ESI) for Metallomics # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mo_albupd_0m _database_code_depnum_ccdc_archive 'CCDC 855686' #TrackingRef 'mo_albupd_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dichlorobis(3-allyl-1-butylimdazolium)palladium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Cl2 N4 Pd' _chemical_formula_weight 505.80 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 ? _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 7.5573(8) _cell_length_b 14.3118(15) _cell_length_c 22.254(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.258(2) _cell_angle_gamma 90.00 _cell_volume 2400.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7623 _exptl_absorpt_correction_T_max 0.8419 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35851 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 34.62 _reflns_number_total 10084 _reflns_number_gt 6059 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0884P)^2^+2.5994P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10084 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.39184(4) 0.499553(16) 0.157098(12) 0.03583(9) Uani 1 1 d . . . Cl1 Cl 0.30677(13) 0.35302(6) 0.11457(4) 0.0439(2) Uani 1 1 d . . . Cl2 Cl 0.17117(15) 0.49135(7) 0.22766(6) 0.0525(2) Uani 1 1 d . . . N1 N 0.6272(5) 0.5660(2) 0.06130(14) 0.0466(7) Uani 1 1 d . . . N2 N 0.7451(4) 0.4541(2) 0.11386(15) 0.0463(7) Uani 1 1 d . . . N3 N 0.3405(5) 0.7020(2) 0.17834(16) 0.0520(8) Uani 1 1 d . . . N4 N 0.5903(5) 0.6582(2) 0.22162(15) 0.0474(7) Uani 1 1 d . . . C1 C 0.5905(17) 0.8010(5) 0.0155(3) 0.132(4) Uani 1 1 d . . . H12B H 0.5605 0.7914 -0.0254 0.159 Uiso 1 1 calc R . . H12C H 0.6335 0.8587 0.0289 0.159 Uiso 1 1 calc R . . C2 C 0.5726(9) 0.7345(3) 0.0532(2) 0.0708(15) Uani 1 1 d . . . H2A H 0.6038 0.7464 0.0937 0.085 Uiso 1 1 calc R . . C3 C 0.5034(7) 0.6370(3) 0.03603(18) 0.0562(11) Uani 1 1 d . . . H3A H 0.3878 0.6278 0.0514 0.067 Uiso 1 1 calc R . . H3B H 0.4904 0.6311 -0.0075 0.067 Uiso 1 1 calc R . . C4 C 0.7920(7) 0.5529(4) 0.0413(2) 0.0653(13) Uani 1 1 d . . . H4A H 0.8418 0.5860 0.0107 0.078 Uiso 1 1 calc R . . C5 C 0.8678(8) 0.4833(4) 0.0740(2) 0.0642(13) Uani 1 1 d . . . H5A H 0.9808 0.4590 0.0708 0.077 Uiso 1 1 calc R . . C6 C 0.5960(6) 0.5061(2) 0.10664(17) 0.0417(7) Uani 1 1 d . . . C7 C 0.7744(7) 0.3760(3) 0.1554(2) 0.0594(11) Uani 1 1 d . . . H7A H 0.6739 0.3695 0.1798 0.071 Uiso 1 1 calc R . . H7B H 0.8796 0.3873 0.1821 0.071 Uiso 1 1 calc R . . C8 C 0.7980(12) 0.2856(5) 0.1190(4) 0.109(3) Uani 1 1 d . . . H8A H 0.6838 0.2688 0.0992 0.131 Uiso 1 1 calc R . . H8B H 0.8772 0.2990 0.0878 0.131 Uiso 1 1 calc R . . C9 C 0.8621(17) 0.2105(6) 0.1504(4) 0.128(3) Uani 1 1 d . . . H9A H 0.7835 0.1953 0.1815 0.154 Uiso 1 1 calc R . . H9B H 0.9778 0.2254 0.1699 0.154 Uiso 1 1 calc R . . C10 C 0.879(2) 0.1241(8) 0.1080(8) 0.199(7) Uani 1 1 d . . . H10A H 0.9216 0.0713 0.1313 0.299 Uiso 1 1 calc R . . H10B H 0.9600 0.1384 0.0781 0.299 Uiso 1 1 calc R . . H10C H 0.7643 0.1097 0.0884 0.299 Uiso 1 1 calc R . . C11 C -0.0349(10) 0.8364(5) 0.1422(5) 0.112(3) Uani 1 1 d . . . H11A H -0.0116 0.8506 0.1027 0.134 Uiso 1 1 calc R . . H11B H -0.1147 0.8725 0.1620 0.134 Uiso 1 1 calc R . . C12 C 0.0440(9) 0.7662(5) 0.1695(3) 0.0902(19) Uani 1 1 d . . . H12A H 0.0169 0.7544 0.2089 0.108 Uiso 1 1 calc R . . C13 C 0.1716(9) 0.7041(4) 0.1439(3) 0.0759(16) Uani 1 1 d . . . H13A H 0.1229 0.6414 0.1416 0.091 Uiso 1 1 calc R . . H13B H 0.1893 0.7243 0.1032 0.091 Uiso 1 1 calc R . . C14 C 0.4184(8) 0.7796(3) 0.2068(2) 0.0638(13) Uani 1 1 d . . . H14A H 0.3708 0.8395 0.2069 0.077 Uiso 1 1 calc R . . C15 C 0.5720(7) 0.7533(3) 0.2337(2) 0.0584(11) Uani 1 1 d . . . H15A H 0.6525 0.7908 0.2562 0.070 Uiso 1 1 calc R . . C16 C 0.4506(5) 0.6266(2) 0.18794(16) 0.0420(7) Uani 1 1 d . . . C17 C 0.7366(6) 0.6010(3) 0.2456(2) 0.0591(11) Uani 1 1 d . . . H17A H 0.8306 0.6412 0.2627 0.071 Uiso 1 1 calc R . . H17B H 0.7831 0.5659 0.2129 0.071 Uiso 1 1 calc R . . C18 C 0.6842(8) 0.5348(4) 0.2925(3) 0.0734(14) Uani 1 1 d . . . H18A H 0.5958 0.4925 0.2740 0.088 Uiso 1 1 calc R . . H18B H 0.7872 0.4976 0.3056 0.088 Uiso 1 1 calc R . . C19 C 0.6131(13) 0.5756(5) 0.3458(3) 0.103(3) Uani 1 1 d . . . H19A H 0.5105 0.6133 0.3330 0.123 Uiso 1 1 calc R . . H19B H 0.7019 0.6169 0.3650 0.123 Uiso 1 1 calc R . . C20 C 0.560(3) 0.5064(5) 0.3912(5) 0.162(7) Uani 1 1 d . . . H20A H 0.5135 0.5388 0.4244 0.244 Uiso 1 1 calc R . . H20B H 0.6615 0.4703 0.4055 0.244 Uiso 1 1 calc R . . H20C H 0.4705 0.4656 0.3729 0.244 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 0.03410(14) 0.03282(13) 0.04020(14) -0.00193(9) 0.00035(9) -0.00025(9) Cl1 0.0478(5) 0.0341(3) 0.0487(4) -0.0030(3) -0.0034(4) -0.0039(3) Cl2 0.0388(5) 0.0577(6) 0.0625(6) -0.0067(4) 0.0151(4) -0.0037(4) N1 0.0486(19) 0.0510(17) 0.0406(15) -0.0047(13) 0.0065(14) -0.0035(14) N2 0.0350(16) 0.0538(18) 0.0498(17) -0.0090(14) 0.0005(13) 0.0061(14) N3 0.063(2) 0.0385(15) 0.0544(18) -0.0088(13) -0.0004(17) 0.0061(15) N4 0.0437(18) 0.0465(16) 0.0518(17) -0.0119(13) 0.0028(14) -0.0071(14) C1 0.260(13) 0.056(3) 0.080(4) 0.000(3) 0.012(6) -0.029(5) C2 0.107(5) 0.053(2) 0.054(2) -0.0048(19) 0.009(3) -0.006(3) C3 0.080(3) 0.049(2) 0.0387(18) 0.0008(15) 0.0019(19) 0.002(2) C4 0.058(3) 0.087(4) 0.053(2) -0.002(2) 0.018(2) -0.001(3) C5 0.049(3) 0.085(3) 0.060(3) -0.015(2) 0.015(2) 0.004(2) C6 0.047(2) 0.0379(16) 0.0397(16) -0.0057(13) -0.0001(14) -0.0016(14) C7 0.052(3) 0.046(2) 0.078(3) 0.0008(19) -0.011(2) 0.0075(18) C8 0.103(6) 0.064(4) 0.160(7) -0.005(4) 0.014(5) 0.020(4) C9 0.170(10) 0.093(6) 0.118(6) 0.001(4) -0.014(6) 0.043(6) C10 0.175(12) 0.101(7) 0.33(2) -0.059(9) 0.054(12) 0.050(7) C11 0.074(4) 0.075(4) 0.184(8) -0.027(5) -0.007(5) 0.031(4) C12 0.074(4) 0.096(5) 0.103(5) -0.008(4) 0.023(4) 0.000(4) C13 0.086(4) 0.056(3) 0.082(3) -0.013(2) -0.016(3) 0.027(3) C14 0.084(4) 0.0396(19) 0.069(3) -0.0125(19) 0.014(3) 0.001(2) C15 0.071(3) 0.046(2) 0.059(2) -0.0199(18) 0.010(2) -0.016(2) C16 0.0440(19) 0.0397(16) 0.0429(17) -0.0041(13) 0.0069(15) -0.0041(14) C17 0.040(2) 0.067(3) 0.069(3) -0.015(2) -0.006(2) -0.0014(19) C18 0.063(3) 0.066(3) 0.089(4) -0.004(3) -0.008(3) 0.011(3) C19 0.154(8) 0.077(4) 0.078(4) 0.002(3) 0.019(5) -0.002(4) C20 0.32(2) 0.085(6) 0.091(6) 0.011(4) 0.054(10) 0.008(7) _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 C6 1.977(4) . ? Pd1 C16 1.982(4) . ? Pd1 Cl1 2.3699(9) . ? Pd1 Cl2 2.3770(11) . ? N1 C6 1.358(5) . ? N1 C4 1.366(6) . ? N1 C3 1.465(6) . ? N2 C6 1.350(5) . ? N2 C5 1.393(6) . ? N2 C7 1.458(6) . ? N3 C16 1.369(5) . ? N3 C14 1.388(6) . ? N3 C13 1.440(7) . ? N4 C16 1.328(5) . ? N4 C15 1.395(5) . ? N4 C17 1.446(6) . ? C1 C2 1.282(8) . ? C1 H12B 0.9300 . ? C1 H12C 0.9300 . ? C2 C3 1.528(7) . ? C2 H2A 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.338(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C7 C8 1.543(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.351(11) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.567(14) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.298(11) . ? C11 H11A 0.9300 . ? C11 H11B 0.9300 . ? C12 C13 1.458(8) . ? C12 H12A 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.321(8) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C17 C18 1.485(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.459(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.491(12) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? 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 C6 Pd1 C16 89.36(14) . . ? C6 Pd1 Cl1 90.87(10) . . ? C16 Pd1 Cl1 175.66(12) . . ? C6 Pd1 Cl2 173.28(12) . . ? C16 Pd1 Cl2 88.09(11) . . ? Cl1 Pd1 Cl2 92.14(4) . . ? C6 N1 C4 111.6(4) . . ? C6 N1 C3 125.6(4) . . ? C4 N1 C3 122.8(4) . . ? C6 N2 C5 110.4(4) . . ? C6 N2 C7 125.8(4) . . ? C5 N2 C7 123.8(4) . . ? C16 N3 C14 109.1(4) . . ? C16 N3 C13 127.2(3) . . ? C14 N3 C13 123.7(4) . . ? C16 N4 C15 110.8(4) . . ? C16 N4 C17 124.7(3) . . ? C15 N4 C17 124.4(4) . . ? C2 C1 H12B 120.0 . . ? C2 C1 H12C 120.0 . . ? H12B C1 H12C 120.0 . . ? C1 C2 C3 124.4(5) . . ? C1 C2 H2A 117.8 . . ? C3 C2 H2A 117.8 . . ? N1 C3 C2 109.9(4) . . ? N1 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? N1 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 N1 106.8(4) . . ? C5 C4 H4A 126.6 . . ? N1 C4 H4A 126.6 . . ? C4 C5 N2 106.9(5) . . ? C4 C5 H5A 126.5 . . ? N2 C5 H5A 126.5 . . ? N2 C6 N1 104.3(4) . . ? N2 C6 Pd1 125.9(3) . . ? N1 C6 Pd1 129.7(3) . . ? N2 C7 C8 109.2(5) . . ? N2 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N2 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 116.5(8) . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C8 C9 C10 110.9(10) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.0 . . ? 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 . . ? C12 C11 H11A 120.0 . . ? C12 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? C11 C12 C13 125.6(8) . . ? C11 C12 H12A 117.2 . . ? C13 C12 H12A 117.2 . . ? N3 C13 C12 113.0(5) . . ? N3 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? N3 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C15 C14 N3 107.9(4) . . ? C15 C14 H14A 126.0 . . ? N3 C14 H14A 126.0 . . ? C14 C15 N4 106.7(4) . . ? C14 C15 H15A 126.7 . . ? N4 C15 H15A 126.7 . . ? N4 C16 N3 105.5(3) . . ? N4 C16 Pd1 131.0(3) . . ? N3 C16 Pd1 123.4(3) . . ? N4 C17 C18 112.6(4) . . ? N4 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? N4 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? C19 C18 C17 116.8(5) . . ? C19 C18 H18A 108.1 . . ? C17 C18 H18A 108.1 . . ? C19 C18 H18B 108.1 . . ? C17 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C18 C19 C20 114.8(7) . . ? C18 C19 H19A 108.6 . . ? C20 C19 H19A 108.6 . . ? C18 C19 H19B 108.6 . . ? C20 C19 H19B 108.6 . . ? H19A C19 H19B 107.5 . . ? 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 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C3 C2 110.5(5) . . . . ? C4 N1 C3 C2 -69.2(5) . . . . ? C1 C2 C3 N1 128.0(9) . . . . ? C6 N1 C4 C5 0.2(6) . . . . ? C3 N1 C4 C5 180.0(4) . . . . ? N1 C4 C5 N2 0.5(6) . . . . ? C6 N2 C5 C4 -1.0(6) . . . . ? C7 N2 C5 C4 176.8(4) . . . . ? C5 N2 C6 N1 1.1(4) . . . . ? C7 N2 C6 N1 -176.7(4) . . . . ? C5 N2 C6 Pd1 -174.3(3) . . . . ? C7 N2 C6 Pd1 7.9(6) . . . . ? C4 N1 C6 N2 -0.8(5) . . . . ? C3 N1 C6 N2 179.4(4) . . . . ? C4 N1 C6 Pd1 174.4(3) . . . . ? C3 N1 C6 Pd1 -5.4(6) . . . . ? C16 Pd1 C6 N2 112.3(3) . . . . ? Cl1 Pd1 C6 N2 -72.0(3) . . . . ? Cl2 Pd1 C6 N2 44.6(10) . . . . ? C16 Pd1 C6 N1 -62.0(4) . . . . ? Cl1 Pd1 C6 N1 113.7(3) . . . . ? Cl2 Pd1 C6 N1 -129.7(8) . . . . ? C6 N2 C7 C8 116.0(5) . . . . ? C5 N2 C7 C8 -61.5(6) . . . . ? N2 C7 C8 C9 166.8(8) . . . . ? C7 C8 C9 C10 179.9(9) . . . . ? C16 N3 C13 C12 144.2(5) . . . . ? C14 N3 C13 C12 -36.9(8) . . . . ? C11 C12 C13 N3 122.1(8) . . . . ? C16 N3 C14 C15 -0.4(5) . . . . ? C13 N3 C14 C15 -179.5(5) . . . . ? N3 C14 C15 N4 0.2(5) . . . . ? C16 N4 C15 C14 0.0(5) . . . . ? C17 N4 C15 C14 -176.6(4) . . . . ? C15 N4 C16 N3 -0.3(5) . . . . ? C17 N4 C16 N3 176.3(4) . . . . ? C15 N4 C16 Pd1 -178.4(3) . . . . ? C17 N4 C16 Pd1 -1.8(6) . . . . ? C14 N3 C16 N4 0.4(5) . . . . ? C13 N3 C16 N4 179.5(5) . . . . ? C14 N3 C16 Pd1 178.7(3) . . . . ? C13 N3 C16 Pd1 -2.2(6) . . . . ? C6 Pd1 C16 N4 -65.8(4) . . . . ? Cl1 Pd1 C16 N4 -158.9(12) . . . . ? Cl2 Pd1 C16 N4 108.0(4) . . . . ? C6 Pd1 C16 N3 116.4(3) . . . . ? Cl1 Pd1 C16 N3 23.3(17) . . . . ? Cl2 Pd1 C16 N3 -69.8(3) . . . . ? C16 N4 C17 C18 -68.2(6) . . . . ? C15 N4 C17 C18 107.9(5) . . . . ? N4 C17 C18 C19 -59.6(7) . . . . ? C17 C18 C19 C20 179.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 34.62 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.117 _refine_diff_density_min -1.256 _refine_diff_density_rms 0.118 data_mo_alympdb_0m _database_code_depnum_ccdc_archive 'CCDC 855687' #TrackingRef 'mo_alympdb_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dichlorobis(3-allyl-1-methylimidazolium)palladium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Br0 Cl2 N4 Pd' _chemical_formula_weight 421.64 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5862(6) _cell_length_b 7.6268(5) _cell_length_c 8.1960(5) _cell_angle_alpha 78.9760(10) _cell_angle_beta 73.148(2) _cell_angle_gamma 69.4720(10) _cell_volume 422.90(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6604 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 29.50 _reflns_number_total 2311 _reflns_number_gt 2164 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0628P)^2^+2.6537P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2311 _refine_ls_number_parameters 99 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1519 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 1.237 _refine_ls_restrained_S_all 1.237 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.0000 0.0000 0.0000 0.01751(17) Uani 1 2 d S . . Cl1 Cl 0.21396(15) -0.11305(14) -0.25713(13) 0.0157(2) Uani 1 1 d . . . N1 N 0.1811(6) 0.3170(6) -0.1060(5) 0.0205(8) Uani 1 1 d . . . N2 N 0.2731(6) 0.1412(6) 0.1098(6) 0.0222(8) Uani 1 1 d . . . C1 C 0.1622(7) 0.1624(7) 0.0008(6) 0.0203(9) Uani 1 1 d . . . C2 C 0.3033(8) 0.3926(8) -0.0660(7) 0.0256(10) Uani 1 1 d . . . H2A H 0.3371 0.4988 -0.1212 0.031 Uiso 1 1 calc R . . C3 C 0.3632(8) 0.2807(8) 0.0692(7) 0.0255(10) Uani 1 1 d . . . H3A H 0.4481 0.2939 0.1247 0.031 Uiso 1 1 calc R . . C4 C 0.2923(9) -0.0021(8) 0.2559(7) 0.0303(12) Uani 1 1 d . . . H4A H 0.2517 -0.1029 0.2413 0.045 Uiso 1 1 calc R . . H4B H 0.2125 0.0527 0.3594 0.045 Uiso 1 1 calc R . . H4C H 0.4253 -0.0503 0.2629 0.045 Uiso 1 1 calc R . . C5 C 0.0915(8) 0.3954(8) -0.2524(7) 0.0244(10) Uani 1 1 d . . . H5A H 0.0227 0.5285 -0.2447 0.029 Uiso 1 1 calc R . . H5B H -0.0018 0.3334 -0.2486 0.029 Uiso 1 1 calc R . . C6 C 0.2442(8) 0.3684(9) -0.4206(7) 0.0285(11) Uani 1 1 d . . . H6A H 0.3172 0.2471 -0.4491 0.034 Uiso 1 1 calc R . . C7 C 0.2757(10) 0.5136(10) -0.5272(7) 0.0357(13) Uani 1 1 d . . . H7A H 0.2035 0.6354 -0.4999 0.043 Uiso 1 1 calc R . . H7B H 0.3700 0.4942 -0.6298 0.043 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 0.0227(3) 0.0183(3) 0.0155(3) 0.00213(17) -0.00829(18) -0.01042(19) Cl1 0.0199(5) 0.0168(5) 0.0129(5) -0.0013(4) -0.0039(4) -0.0089(4) N1 0.0227(19) 0.0222(19) 0.0200(19) 0.0004(15) -0.0076(16) -0.0106(16) N2 0.026(2) 0.024(2) 0.021(2) -0.0021(16) -0.0100(17) -0.0088(17) C1 0.022(2) 0.023(2) 0.017(2) 0.0008(17) -0.0059(17) -0.0087(18) C2 0.025(2) 0.030(3) 0.026(2) -0.002(2) -0.003(2) -0.017(2) C3 0.024(2) 0.033(3) 0.024(2) -0.004(2) -0.0068(19) -0.015(2) C4 0.040(3) 0.029(3) 0.026(3) 0.006(2) -0.019(2) -0.012(2) C5 0.027(2) 0.027(2) 0.021(2) 0.0054(19) -0.0082(19) -0.013(2) C6 0.030(3) 0.035(3) 0.023(2) -0.003(2) -0.010(2) -0.010(2) C7 0.047(4) 0.048(4) 0.019(2) -0.005(2) -0.003(2) -0.027(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 C1 2.031(5) 2 ? Pd1 C1 2.031(5) . ? Pd1 Cl1 2.3557(10) 2 ? Pd1 Cl1 2.3557(10) . ? N1 C1 1.352(6) . ? N1 C2 1.386(6) . ? N1 C5 1.475(6) . ? N2 C1 1.348(6) . ? N2 C3 1.397(7) . ? N2 C4 1.463(7) . ? C2 C3 1.350(8) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.516(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.320(9) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C7 H7B 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 C1 180.0 2 . ? C1 Pd1 Cl1 90.01(14) 2 2 ? C1 Pd1 Cl1 89.99(14) . 2 ? C1 Pd1 Cl1 89.99(14) 2 . ? C1 Pd1 Cl1 90.01(14) . . ? Cl1 Pd1 Cl1 180.0 2 . ? C1 N1 C2 111.7(4) . . ? C1 N1 C5 125.5(4) . . ? C2 N1 C5 122.7(4) . . ? C1 N2 C3 110.8(4) . . ? C1 N2 C4 125.5(4) . . ? C3 N2 C4 123.7(4) . . ? N2 C1 N1 104.6(4) . . ? N2 C1 Pd1 127.6(4) . . ? N1 C1 Pd1 127.8(3) . . ? C3 C2 N1 106.0(5) . . ? C3 C2 H2A 127.0 . . ? N1 C2 H2A 127.0 . . ? C2 C3 N2 106.8(4) . . ? C2 C3 H3A 126.6 . . ? N2 C3 H3A 126.6 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C6 110.8(4) . . ? N1 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 121.3(6) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 H7A 120.0 . . ? C6 C7 H7B 120.0 . . ? H7A C7 H7B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 -0.9(6) . . . . ? C4 N2 C1 N1 176.7(5) . . . . ? C3 N2 C1 Pd1 179.9(4) . . . . ? C4 N2 C1 Pd1 -2.5(8) . . . . ? C2 N1 C1 N2 0.3(6) . . . . ? C5 N1 C1 N2 178.0(5) . . . . ? C2 N1 C1 Pd1 179.5(4) . . . . ? C5 N1 C1 Pd1 -2.8(7) . . . . ? C1 Pd1 C1 N2 -53.0(5) 2 . . . ? Cl1 Pd1 C1 N2 69.1(5) 2 . . . ? Cl1 Pd1 C1 N2 -110.9(5) . . . . ? C1 Pd1 C1 N1 128.0(5) 2 . . . ? Cl1 Pd1 C1 N1 -109.9(4) 2 . . . ? Cl1 Pd1 C1 N1 70.1(4) . . . . ? C1 N1 C2 C3 0.4(6) . . . . ? C5 N1 C2 C3 -177.4(5) . . . . ? N1 C2 C3 N2 -0.9(6) . . . . ? C1 N2 C3 C2 1.2(6) . . . . ? C4 N2 C3 C2 -176.4(5) . . . . ? C1 N1 C5 C6 -110.6(6) . . . . ? C2 N1 C5 C6 66.9(6) . . . . ? N1 C5 C6 C7 -117.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 2.174 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.229 data_mo_papd_0m _database_code_depnum_ccdc_archive 'CCDC 855689' #TrackingRef 'mo_papd_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dichlorobis(3-benzyl-1-butylimdazolium)palladium(II) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 Cl2 N4 Pd' _chemical_formula_weight 605.91 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 ? _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 11.629(3) _cell_length_b 8.662(2) _cell_length_c 16.710(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.315(13) _cell_angle_gamma 90.00 _cell_volume 1422.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5935 _exptl_absorpt_correction_T_max 0.9020 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14786 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 32.49 _reflns_number_total 5067 _reflns_number_gt 4117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1008P)^2^+1.2360P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5067 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1542 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.0000 0.0000 0.5000 0.03365(11) Uani 1 2 d S . . Cl1 Cl 0.13562(7) -0.11886(8) 0.45238(5) 0.03901(16) Uani 1 1 d . . . N1 N -0.2038(3) -0.2606(3) 0.4470(2) 0.0441(5) Uani 1 1 d . . . N2 N -0.0106(3) -0.3203(3) 0.57017(19) 0.0437(5) Uani 1 1 d . . . C1 C -0.2151(4) -0.2682(5) 0.2636(3) 0.0524(8) Uani 1 1 d . . . H1A H -0.1281 -0.2444 0.3141 0.063 Uiso 1 1 calc R . . C2 C -0.2328(5) -0.3265(5) 0.1799(3) 0.0606(9) Uani 1 1 d . . . H2A H -0.1574 -0.3429 0.1754 0.073 Uiso 1 1 calc R . . C3 C -0.3600(5) -0.3598(6) 0.1045(3) 0.0672(11) Uani 1 1 d . . . H3A H -0.3712 -0.3969 0.0485 0.081 Uiso 1 1 calc R . . C4 C -0.4731(5) -0.3378(6) 0.1118(3) 0.0729(12) Uani 1 1 d . . . H4A H -0.5600 -0.3609 0.0609 0.088 Uiso 1 1 calc R . . C5 C -0.4553(4) -0.2817(6) 0.1949(3) 0.0626(10) Uani 1 1 d . . . H5A H -0.5308 -0.2677 0.1995 0.075 Uiso 1 1 calc R . . C6 C -0.3263(3) -0.2454(4) 0.2722(2) 0.0461(7) Uani 1 1 d . . . C7 C -0.3092(3) -0.1806(5) 0.3617(3) 0.0513(7) Uani 1 1 d . . . H7A H -0.2859 -0.0720 0.3665 0.062 Uiso 1 1 calc R . . H7B H -0.3951 -0.1884 0.3580 0.062 Uiso 1 1 calc R . . C8 C -0.0759(3) -0.2065(3) 0.5058(2) 0.0378(5) Uani 1 1 d . . . C9 C -0.2174(4) -0.4067(5) 0.4750(3) 0.0570(9) Uani 1 1 d . . . H9A H -0.2954 -0.4675 0.4457 0.068 Uiso 1 1 calc R . . C10 C -0.0977(5) -0.4437(5) 0.5516(3) 0.0561(8) Uani 1 1 d . . . H10A H -0.0765 -0.5349 0.5861 0.067 Uiso 1 1 calc R . . C11 C 0.1323(4) -0.3122(4) 0.6482(2) 0.0510(7) Uani 1 1 d . . . H11A H 0.1851 -0.2674 0.6246 0.061 Uiso 1 1 calc R . . H11B H 0.1656 -0.4163 0.6693 0.061 Uiso 1 1 calc R . . C12 C 0.1563(4) -0.2194(5) 0.7317(3) 0.0551(8) Uani 1 1 d . . . H12A H 0.1129 -0.2698 0.7607 0.066 Uiso 1 1 calc R . . H12B H 0.1161 -0.1178 0.7107 0.066 Uiso 1 1 calc R . . C13 C 0.3084(4) -0.2037(6) 0.8042(3) 0.0676(11) Uani 1 1 d . . . H13A H 0.3472 -0.3059 0.8248 0.081 Uiso 1 1 calc R . . H13B H 0.3510 -0.1560 0.7738 0.081 Uiso 1 1 calc R . . C14 C 0.3414(6) -0.1102(7) 0.8891(3) 0.0767(13) Uani 1 1 d . . . H14A H 0.4371 -0.1170 0.9357 0.115 Uiso 1 1 calc R . . H14B H 0.2912 -0.1492 0.9154 0.115 Uiso 1 1 calc R . . H14C H 0.3170 -0.0043 0.8709 0.115 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 0.03226(16) 0.03093(16) 0.03923(17) 0.00167(9) 0.02010(12) -0.00053(9) Cl1 0.0384(3) 0.0344(3) 0.0555(4) -0.0055(3) 0.0326(3) -0.0013(2) N1 0.0448(12) 0.0430(13) 0.0466(13) -0.0039(10) 0.0259(11) -0.0083(10) N2 0.0503(14) 0.0369(12) 0.0462(13) 0.0030(10) 0.0274(11) -0.0005(10) C1 0.0453(15) 0.056(2) 0.0521(17) -0.0011(15) 0.0233(14) -0.0002(14) C2 0.064(2) 0.064(2) 0.061(2) 0.0004(18) 0.0386(18) 0.0025(18) C3 0.077(3) 0.074(3) 0.0495(19) -0.0072(18) 0.0332(19) -0.010(2) C4 0.062(2) 0.084(3) 0.0493(19) -0.009(2) 0.0138(17) -0.017(2) C5 0.0422(16) 0.084(3) 0.0559(19) -0.0008(19) 0.0224(15) -0.0113(18) C6 0.0389(13) 0.0493(17) 0.0440(14) 0.0005(12) 0.0181(12) -0.0051(12) C7 0.0397(14) 0.058(2) 0.0515(17) -0.0056(15) 0.0214(13) 0.0005(13) C8 0.0399(12) 0.0361(13) 0.0423(13) -0.0003(10) 0.0251(11) -0.0018(10) C9 0.068(2) 0.0488(19) 0.064(2) -0.0095(15) 0.0415(19) -0.0224(16) C10 0.076(2) 0.0391(16) 0.060(2) 0.0032(15) 0.0413(19) -0.0097(17) C11 0.0503(16) 0.0494(18) 0.0502(16) 0.0093(14) 0.0248(14) 0.0113(14) C12 0.0516(17) 0.060(2) 0.0496(17) -0.0006(15) 0.0239(15) 0.0058(16) C13 0.056(2) 0.077(3) 0.066(2) -0.003(2) 0.0294(19) 0.009(2) C14 0.075(3) 0.081(3) 0.060(2) -0.005(2) 0.027(2) -0.007(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 C8 2.020(3) . ? Pd1 C8 2.020(3) 3_556 ? Pd1 Cl1 2.3500(7) . ? Pd1 Cl1 2.3500(7) 3_556 ? N1 C8 1.354(4) . ? N1 C9 1.388(5) . ? N1 C7 1.465(5) . ? N2 C8 1.354(4) . ? N2 C10 1.389(5) . ? N2 C11 1.467(4) . ? C1 C6 1.389(5) . ? C1 C2 1.396(6) . ? C1 H1A 0.9300 . ? C2 C3 1.366(6) . ? C2 H2A 0.9300 . ? C3 C4 1.399(7) . ? C3 H3A 0.9300 . ? C4 C5 1.377(7) . ? C4 H4A 0.9300 . ? C5 C6 1.394(5) . ? C5 H5A 0.9300 . ? C6 C7 1.508(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.332(6) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.501(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.525(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.495(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 Pd1 C8 180.0 . 3_556 ? C8 Pd1 Cl1 91.05(8) . . ? C8 Pd1 Cl1 88.95(8) 3_556 . ? C8 Pd1 Cl1 88.95(8) . 3_556 ? C8 Pd1 Cl1 91.05(8) 3_556 3_556 ? Cl1 Pd1 Cl1 180.0 . 3_556 ? C8 N1 C9 110.5(3) . . ? C8 N1 C7 124.5(3) . . ? C9 N1 C7 124.9(3) . . ? C8 N2 C10 110.5(3) . . ? C8 N2 C11 124.0(3) . . ? C10 N2 C11 125.5(3) . . ? C6 C1 C2 120.5(3) . . ? C6 C1 H1A 119.7 . . ? C2 C1 H1A 119.7 . . ? C3 C2 C1 120.6(4) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 121.4(4) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C1 C6 C5 118.2(3) . . ? C1 C6 C7 121.2(3) . . ? C5 C6 C7 120.6(3) . . ? N1 C7 C6 112.8(3) . . ? N1 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N2 C8 N1 104.9(3) . . ? N2 C8 Pd1 127.5(2) . . ? N1 C8 Pd1 127.6(2) . . ? C10 C9 N1 107.1(3) . . ? C10 C9 H9A 126.4 . . ? N1 C9 H9A 126.4 . . ? C9 C10 N2 107.0(3) . . ? C9 C10 H10A 126.5 . . ? N2 C10 H10A 126.5 . . ? N2 C11 C12 114.2(3) . . ? N2 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? N2 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 110.2(3) . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 113.7(4) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.1(7) . . . . ? C1 C2 C3 C4 -1.2(7) . . . . ? C2 C3 C4 C5 0.5(8) . . . . ? C3 C4 C5 C6 0.3(8) . . . . ? C2 C1 C6 C5 -0.3(6) . . . . ? C2 C1 C6 C7 -179.2(4) . . . . ? C4 C5 C6 C1 -0.4(7) . . . . ? C4 C5 C6 C7 178.6(4) . . . . ? C8 N1 C7 C6 100.7(4) . . . . ? C9 N1 C7 C6 -74.3(4) . . . . ? C1 C6 C7 N1 -49.8(5) . . . . ? C5 C6 C7 N1 131.3(4) . . . . ? C10 N2 C8 N1 -0.4(4) . . . . ? C11 N2 C8 N1 179.7(3) . . . . ? C10 N2 C8 Pd1 178.9(2) . . . . ? C11 N2 C8 Pd1 -1.0(4) . . . . ? C9 N1 C8 N2 0.2(4) . . . . ? C7 N1 C8 N2 -175.5(3) . . . . ? C9 N1 C8 Pd1 -179.1(2) . . . . ? C7 N1 C8 Pd1 5.3(5) . . . . ? C8 Pd1 C8 N2 -89(23) 3_556 . . . ? Cl1 Pd1 C8 N2 71.3(3) . . . . ? Cl1 Pd1 C8 N2 -108.7(3) 3_556 . . . ? C8 Pd1 C8 N1 90(23) 3_556 . . . ? Cl1 Pd1 C8 N1 -109.6(3) . . . . ? Cl1 Pd1 C8 N1 70.4(3) 3_556 . . . ? C8 N1 C9 C10 0.1(4) . . . . ? C7 N1 C9 C10 175.7(3) . . . . ? N1 C9 C10 N2 -0.3(4) . . . . ? C8 N2 C10 C9 0.4(4) . . . . ? C11 N2 C10 C9 -179.6(3) . . . . ? C8 N2 C11 C12 79.7(4) . . . . ? C10 N2 C11 C12 -100.2(4) . . . . ? N2 C11 C12 C13 -174.0(3) . . . . ? C11 C12 C13 C14 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 32.49 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 2.046 _refine_diff_density_min -0.907 _refine_diff_density_rms 0.124