# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_d:\30ch40a _database_code_depnum_ccdc_archive 'CCDC 913061' #TrackingRef 'web_deposit_cif_file_0_michaelgardiner_1354099828.compound 4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 I2 N4 O2' _chemical_formula_weight 826.62 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 17.4130(12) _cell_length_b 12.4050(16) _cell_length_c 17.8960(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.474(6) _cell_angle_gamma 90.00 _cell_volume 3864.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 36688 _cell_measurement_theta_min 1.17 _cell_measurement_theta_max 30.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1672 _exptl_absorpt_coefficient_mu 1.661 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Synchrotron ID' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-ID1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q315' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 80553 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 30.94 _reflns_number_total 11973 _reflns_number_gt 8050 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 2008)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0736P)^2^+7.5168P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11973 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _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 I1 I -0.523403(15) 0.86268(2) -0.101265(14) 0.03403(8) Uani 1 1 d . . . I2 I -0.197876(17) 0.86052(3) 0.261918(16) 0.04453(10) Uani 1 1 d . . . O1 O -0.7907(3) 0.9641(3) -0.0454(3) 0.0860(15) Uani 1 1 d . . . O2 O -0.0958(2) 1.1018(3) -0.2691(2) 0.0560(9) Uani 1 1 d . . . N1 N -0.52702(17) 0.7839(2) 0.15940(16) 0.0252(6) Uani 1 1 d . . . N2 N -0.42025(18) 0.8422(2) 0.11574(19) 0.0287(6) Uani 1 1 d . . . N3 N -0.31122(19) 0.8260(3) 0.0349(2) 0.0329(7) Uani 1 1 d . . . N4 N -0.20537(18) 0.7425(3) 0.01578(19) 0.0325(7) Uani 1 1 d . . . C1 C -0.4957(2) 0.8336(3) 0.1021(2) 0.0278(7) Uani 1 1 d . . . H1 H -0.5224 0.8589 0.0586 0.033 Uiso 1 1 calc R . . C2 C -0.4697(2) 0.7612(3) 0.2119(2) 0.0316(8) Uani 1 1 d . . . H2 H -0.4761 0.7259 0.2585 0.038 Uiso 1 1 calc R . . C3 C -0.4033(2) 0.7981(3) 0.1851(2) 0.0332(8) Uani 1 1 d . . . H3 H -0.3541 0.7945 0.2091 0.040 Uiso 1 1 calc R . . C4 C -0.3666(2) 0.9004(3) 0.0681(3) 0.0374(9) Uani 1 1 d . . . H4A H -0.3386 0.9552 0.0983 0.045 Uiso 1 1 calc R . . H4B H -0.3958 0.9382 0.0278 0.045 Uiso 1 1 calc R . . C5 C -0.2403(2) 0.8089(3) 0.0620(2) 0.0327(8) Uani 1 1 d . . . H5 H -0.2187 0.8390 0.1066 0.039 Uiso 1 1 calc R . . C6 C -0.2549(2) 0.7179(4) -0.0432(2) 0.0375(9) Uani 1 1 d . . . H6 H -0.2443 0.6725 -0.0845 0.045 Uiso 1 1 calc R . . C7 C -0.3213(2) 0.7707(4) -0.0309(2) 0.0377(9) Uani 1 1 d . . . H7 H -0.3663 0.7696 -0.0620 0.045 Uiso 1 1 calc R . . C8 C -0.6080(2) 0.7577(3) 0.16742(19) 0.0251(7) Uani 1 1 d . . . C9 C -0.6332(2) 0.6559(3) 0.1442(2) 0.0304(8) Uani 1 1 d . . . C10 C -0.7100(2) 0.6304(3) 0.1570(2) 0.0362(9) Uani 1 1 d . . . H10 H -0.7298 0.5623 0.1417 0.043 Uiso 1 1 calc R . . C11 C -0.7576(2) 0.7037(4) 0.1919(3) 0.0390(9) Uani 1 1 d . . . H11 H -0.8092 0.6842 0.2014 0.047 Uiso 1 1 calc R . . C12 C -0.7312(2) 0.8044(4) 0.2131(2) 0.0350(8) Uani 1 1 d . . . H12 H -0.7651 0.8540 0.2355 0.042 Uiso 1 1 calc R . . C13 C -0.6553(2) 0.8336(3) 0.2019(2) 0.0295(7) Uani 1 1 d . . . C14 C -0.5818(2) 0.5740(3) 0.1065(2) 0.0340(8) Uani 1 1 d . . . H14 H -0.5287 0.6047 0.1056 0.041 Uiso 1 1 calc R . . C15 C -0.5783(3) 0.4694(4) 0.1514(3) 0.0460(11) Uani 1 1 d . . . H15A H -0.5451 0.4177 0.1265 0.069 Uiso 1 1 calc R . . H15B H -0.6301 0.4393 0.1549 0.069 Uiso 1 1 calc R . . H15C H -0.5575 0.4843 0.2018 0.069 Uiso 1 1 calc R . . C16 C -0.6088(3) 0.5540(4) 0.0256(3) 0.0494(12) Uani 1 1 d . . . H16A H -0.5750 0.5011 0.0026 0.074 Uiso 1 1 calc R . . H16B H -0.6073 0.6218 -0.0024 0.074 Uiso 1 1 calc R . . H16C H -0.6615 0.5263 0.0250 0.074 Uiso 1 1 calc R . . C17 C -0.6263(2) 0.9430(3) 0.2292(2) 0.0323(8) Uani 1 1 d . . . H17 H -0.5722 0.9524 0.2129 0.039 Uiso 1 1 calc R . . C18 C -0.6749(3) 1.0347(3) 0.1964(3) 0.0401(9) Uani 1 1 d . . . H18A H -0.6549 1.1039 0.2149 0.060 Uiso 1 1 calc R . . H18B H -0.7283 1.0261 0.2114 0.060 Uiso 1 1 calc R . . H18C H -0.6727 1.0331 0.1417 0.060 Uiso 1 1 calc R . . C19 C -0.6265(3) 0.9460(4) 0.3148(2) 0.0427(10) Uani 1 1 d . . . H19A H -0.6079 1.0164 0.3324 0.064 Uiso 1 1 calc R . . H19B H -0.5929 0.8891 0.3350 0.064 Uiso 1 1 calc R . . H19C H -0.6790 0.9346 0.3318 0.064 Uiso 1 1 calc R . . C20 C -0.1288(2) 0.6982(3) 0.0280(2) 0.0338(8) Uani 1 1 d . . . C21 C -0.0679(2) 0.7384(4) -0.0122(3) 0.0387(9) Uani 1 1 d . . . C22 C 0.0046(3) 0.6922(4) 0.0022(3) 0.0422(10) Uani 1 1 d . . . H22 H 0.0476 0.7174 -0.0243 0.051 Uiso 1 1 calc R . . C23 C 0.0147(3) 0.6109(4) 0.0541(3) 0.0445(11) Uani 1 1 d . . . C24 C -0.0479(3) 0.5739(4) 0.0924(3) 0.0443(10) Uani 1 1 d . . . H24 H -0.0407 0.5174 0.1277 0.053 Uiso 1 1 calc R . . C25 C -0.1209(3) 0.6163(4) 0.0809(3) 0.0404(10) Uani 1 1 d . . . C26 C -0.0790(3) 0.8269(4) -0.0681(3) 0.0502(12) Uani 1 1 d . . . H26A H -0.1059 0.7986 -0.1127 0.075 Uiso 1 1 calc R . . H26B H -0.0288 0.8554 -0.0819 0.075 Uiso 1 1 calc R . . H26C H -0.1096 0.8847 -0.0463 0.075 Uiso 1 1 calc R . . C27 C 0.0939(3) 0.5633(5) 0.0703(3) 0.0572(14) Uani 1 1 d . . . H27A H 0.0948 0.4882 0.0534 0.086 Uiso 1 1 calc R . . H27B H 0.1053 0.5663 0.1242 0.086 Uiso 1 1 calc R . . H27C H 0.1325 0.6049 0.0437 0.086 Uiso 1 1 calc R . . C28 C -0.1895(3) 0.5735(4) 0.1221(3) 0.0515(12) Uani 1 1 d . . . H28A H -0.1782 0.5008 0.1406 0.077 Uiso 1 1 calc R . . H28B H -0.2344 0.5712 0.0880 0.077 Uiso 1 1 calc R . . H28C H -0.2002 0.6210 0.1643 0.077 Uiso 1 1 calc R . . C29 C -0.8153(5) 0.8918(7) -0.1055(5) 0.108(3) Uani 1 1 d . . . H29A H -0.8027 0.9220 -0.1549 0.129 Uiso 1 1 calc R . . H29B H -0.8713 0.8782 -0.1043 0.129 Uiso 1 1 calc R . . C30 C -0.7705(5) 0.7903(6) -0.0897(5) 0.089(2) Uani 1 1 d . . . H30A H -0.8026 0.7253 -0.0982 0.107 Uiso 1 1 calc R . . H30B H -0.7244 0.7858 -0.1208 0.107 Uiso 1 1 calc R . . C31 C -0.7497(6) 0.8039(11) -0.0101(5) 0.121(4) Uani 1 1 d . . . H31A H -0.7730 0.7458 0.0197 0.145 Uiso 1 1 calc R . . H31B H -0.6932 0.8006 -0.0027 0.145 Uiso 1 1 calc R . . C32 C -0.7760(8) 0.8999(8) 0.0113(5) 0.130(4) Uani 1 1 d . . . H32A H -0.8234 0.8894 0.0397 0.156 Uiso 1 1 calc R . . H32B H -0.7373 0.9343 0.0451 0.156 Uiso 1 1 calc R . . C33 C -0.0400(3) 1.1865(5) -0.2710(4) 0.0703(18) Uani 1 1 d . . . H33A H -0.0636 1.2552 -0.2878 0.084 Uiso 1 1 calc R . . H33B H 0.0025 1.1679 -0.3044 0.084 Uiso 1 1 calc R . . C34 C -0.0123(4) 1.1929(8) -0.1903(5) 0.100(3) Uani 1 1 d . . . H34A H 0.0396 1.2251 -0.1860 0.120 Uiso 1 1 calc R . . H34B H -0.0481 1.2354 -0.1599 0.120 Uiso 1 1 calc R . . C35 C -0.0115(5) 1.0771(9) -0.1675(5) 0.110(3) Uani 1 1 d . . . H35A H 0.0364 1.0411 -0.1828 0.132 Uiso 1 1 calc R . . H35B H -0.0166 1.0695 -0.1128 0.132 Uiso 1 1 calc R . . C36 C -0.0784(4) 1.0331(7) -0.2078(4) 0.081(2) Uani 1 1 d . . . H36A H -0.0671 0.9594 -0.2259 0.098 Uiso 1 1 calc R . . H36B H -0.1227 1.0291 -0.1744 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 I1 0.03955(15) 0.03156(13) 0.03092(13) -0.00410(10) -0.00009(10) 0.00714(11) I2 0.03713(15) 0.0598(2) 0.03642(16) -0.00318(13) -0.00281(11) 0.00029(13) O1 0.116(4) 0.040(2) 0.103(4) 0.004(2) 0.013(3) -0.011(2) O2 0.0449(19) 0.065(2) 0.057(2) -0.0053(19) -0.0053(16) -0.0057(17) N1 0.0259(14) 0.0252(14) 0.0245(14) 0.0004(12) -0.0025(11) 0.0002(11) N2 0.0275(15) 0.0228(14) 0.0359(17) -0.0004(12) 0.0053(13) 0.0007(11) N3 0.0320(16) 0.0239(14) 0.0432(19) 0.0031(14) 0.0101(14) 0.0056(13) N4 0.0310(16) 0.0323(16) 0.0343(17) 0.0011(14) 0.0055(13) 0.0041(13) C1 0.0266(17) 0.0259(16) 0.0309(18) 0.0029(14) 0.0032(14) 0.0032(13) C2 0.0287(18) 0.040(2) 0.0254(17) 0.0046(16) -0.0051(14) -0.0023(16) C3 0.0271(18) 0.039(2) 0.0332(19) 0.0005(17) -0.0020(15) -0.0012(16) C4 0.034(2) 0.0271(18) 0.052(3) 0.0050(18) 0.0176(18) 0.0062(16) C5 0.0327(19) 0.0295(18) 0.036(2) 0.0008(16) 0.0068(15) 0.0011(15) C6 0.034(2) 0.042(2) 0.037(2) -0.0037(18) 0.0000(16) 0.0041(17) C7 0.033(2) 0.040(2) 0.040(2) 0.0024(18) 0.0022(17) 0.0052(17) C8 0.0240(16) 0.0277(16) 0.0234(16) 0.0021(14) -0.0025(12) -0.0013(13) C9 0.0313(18) 0.0275(18) 0.0320(19) 0.0015(15) -0.0045(15) 0.0017(14) C10 0.0325(19) 0.034(2) 0.042(2) -0.0021(18) -0.0055(16) -0.0061(16) C11 0.0246(18) 0.044(2) 0.048(2) 0.002(2) 0.0002(16) -0.0064(17) C12 0.0278(18) 0.039(2) 0.039(2) -0.0021(18) 0.0035(15) 0.0021(16) C13 0.0287(18) 0.0285(17) 0.0311(18) 0.0003(15) -0.0024(14) -0.0002(14) C14 0.0307(19) 0.0263(17) 0.045(2) -0.0059(17) -0.0018(16) 0.0002(15) C15 0.037(2) 0.032(2) 0.069(3) 0.007(2) -0.001(2) 0.0031(18) C16 0.054(3) 0.046(3) 0.048(3) -0.014(2) -0.001(2) 0.006(2) C17 0.0280(18) 0.0327(19) 0.036(2) -0.0070(16) 0.0011(15) 0.0011(15) C18 0.040(2) 0.031(2) 0.049(3) -0.0007(19) -0.0031(19) 0.0027(17) C19 0.042(2) 0.046(2) 0.041(2) -0.010(2) -0.0045(18) 0.0004(19) C20 0.0288(18) 0.0335(19) 0.039(2) -0.0043(17) 0.0023(16) 0.0063(15) C21 0.032(2) 0.041(2) 0.043(2) -0.0050(19) 0.0039(17) 0.0025(17) C22 0.031(2) 0.045(2) 0.051(3) -0.012(2) 0.0037(18) 0.0006(18) C23 0.033(2) 0.046(2) 0.054(3) -0.015(2) -0.0072(19) 0.0069(18) C24 0.041(2) 0.040(2) 0.051(3) 0.000(2) -0.004(2) 0.0078(19) C25 0.035(2) 0.036(2) 0.050(3) -0.0051(19) -0.0001(18) 0.0059(17) C26 0.038(2) 0.050(3) 0.063(3) 0.008(2) 0.010(2) -0.002(2) C27 0.035(2) 0.066(3) 0.069(3) -0.023(3) -0.011(2) 0.009(2) C28 0.044(3) 0.052(3) 0.059(3) 0.022(2) 0.004(2) 0.011(2) C29 0.112(6) 0.098(6) 0.109(6) 0.049(5) -0.068(5) -0.038(5) C30 0.102(6) 0.067(4) 0.100(6) -0.019(4) 0.031(5) -0.005(4) C31 0.105(7) 0.176(11) 0.082(6) 0.059(7) 0.011(5) 0.053(7) C32 0.232(14) 0.100(7) 0.058(5) 0.005(5) -0.014(6) -0.054(8) C33 0.047(3) 0.048(3) 0.115(6) -0.018(3) -0.003(3) -0.005(2) C34 0.056(4) 0.122(7) 0.122(7) -0.078(6) -0.007(4) -0.006(4) C35 0.079(5) 0.159(10) 0.090(6) 0.029(6) -0.025(4) -0.028(6) C36 0.074(4) 0.110(6) 0.060(4) 0.014(4) -0.003(3) 0.011(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 O1 C32 1.310(10) . ? O1 C29 1.456(10) . ? O2 C36 1.416(8) . ? O2 C33 1.431(7) . ? N1 C1 1.327(5) . ? N1 C2 1.381(4) . ? N1 C8 1.457(4) . ? N2 C1 1.334(5) . ? N2 C3 1.381(5) . ? N2 C4 1.470(5) . ? N3 C5 1.332(5) . ? N3 C7 1.370(6) . ? N3 C4 1.472(5) . ? N4 C5 1.327(5) . ? N4 C6 1.379(5) . ? N4 C20 1.454(5) . ? C1 H1 0.9500 . ? C2 C3 1.345(5) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5 0.9500 . ? C6 C7 1.352(6) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.397(5) . ? C8 C13 1.404(5) . ? C9 C10 1.398(6) . ? C9 C14 1.523(5) . ? C10 C11 1.389(6) . ? C10 H10 0.9500 . ? C11 C12 1.380(6) . ? C11 H11 0.9500 . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? C13 C17 1.524(5) . ? C14 C15 1.527(6) . ? C14 C16 1.531(6) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.527(6) . ? C17 C19 1.532(6) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.388(6) . ? C20 C25 1.393(6) . ? C21 C22 1.405(6) . ? C21 C26 1.494(7) . ? C22 C23 1.378(7) . ? C22 H22 0.9500 . ? C23 C24 1.380(7) . ? C23 C27 1.521(6) . ? C24 C25 1.386(6) . ? C24 H24 0.9500 . ? C25 C28 1.514(7) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C30 1.503(11) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.471(12) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.336(14) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.512(10) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.493(13) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.461(10) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? 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 C32 O1 C29 104.2(6) . . ? C36 O2 C33 109.2(5) . . ? C1 N1 C2 108.5(3) . . ? C1 N1 C8 126.7(3) . . ? C2 N1 C8 124.8(3) . . ? C1 N2 C3 108.7(3) . . ? C1 N2 C4 124.8(3) . . ? C3 N2 C4 126.2(3) . . ? C5 N3 C7 109.3(3) . . ? C5 N3 C4 124.3(4) . . ? C7 N3 C4 126.2(4) . . ? C5 N4 C6 109.1(3) . . ? C5 N4 C20 125.1(4) . . ? C6 N4 C20 125.7(3) . . ? N1 C1 N2 108.6(3) . . ? N1 C1 H1 125.7 . . ? N2 C1 H1 125.7 . . ? C3 C2 N1 107.5(3) . . ? C3 C2 H2 126.3 . . ? N1 C2 H2 126.3 . . ? C2 C3 N2 106.8(3) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 N3 111.1(3) . . ? N2 C4 H4A 109.4 . . ? N3 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? N3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N4 C5 N3 107.9(4) . . ? N4 C5 H5 126.1 . . ? N3 C5 H5 126.1 . . ? C7 C6 N4 106.8(4) . . ? C7 C6 H6 126.6 . . ? N4 C6 H6 126.6 . . ? C6 C7 N3 106.9(4) . . ? C6 C7 H7 126.5 . . ? N3 C7 H7 126.5 . . ? C9 C8 C13 123.6(3) . . ? C9 C8 N1 118.0(3) . . ? C13 C8 N1 118.3(3) . . ? C8 C9 C10 116.8(4) . . ? C8 C9 C14 123.4(3) . . ? C10 C9 C14 119.8(4) . . ? C11 C10 C9 120.6(4) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.5(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 117.3(4) . . ? C12 C13 C17 119.7(4) . . ? C8 C13 C17 123.0(3) . . ? C9 C14 C15 110.5(4) . . ? C9 C14 C16 111.0(3) . . ? C15 C14 C16 111.5(4) . . ? C9 C14 H14 107.9 . . ? C15 C14 H14 107.9 . . ? C16 C14 H14 107.9 . . ? 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 . . ? 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 . . ? C13 C17 C18 111.3(3) . . ? C13 C17 C19 109.5(3) . . ? C18 C17 C19 110.5(3) . . ? C13 C17 H17 108.5 . . ? C18 C17 H17 108.5 . . ? C19 C17 H17 108.5 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 123.4(4) . . ? C21 C20 N4 119.7(4) . . ? C25 C20 N4 116.9(4) . . ? C20 C21 C22 116.9(4) . . ? C20 C21 C26 121.6(4) . . ? C22 C21 C26 121.5(4) . . ? C23 C22 C21 121.4(4) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 119.3(4) . . ? C22 C23 C27 120.7(5) . . ? C24 C23 C27 120.0(5) . . ? C23 C24 C25 122.2(5) . . ? C23 C24 H24 118.9 . . ? C25 C24 H24 118.9 . . ? C24 C25 C20 116.8(4) . . ? C24 C25 C28 121.8(4) . . ? C20 C25 C28 121.4(4) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O1 C29 C30 103.7(6) . . ? O1 C29 H29A 111.0 . . ? C30 C29 H29A 111.0 . . ? O1 C29 H29B 111.0 . . ? C30 C29 H29B 111.0 . . ? H29A C29 H29B 109.0 . . ? C31 C30 C29 101.6(7) . . ? C31 C30 H30A 111.5 . . ? C29 C30 H30A 111.5 . . ? C31 C30 H30B 111.5 . . ? C29 C30 H30B 111.5 . . ? H30A C30 H30B 109.3 . . ? C32 C31 C30 107.6(7) . . ? C32 C31 H31A 110.2 . . ? C30 C31 H31A 110.2 . . ? C32 C31 H31B 110.2 . . ? C30 C31 H31B 110.2 . . ? H31A C31 H31B 108.5 . . ? O1 C32 C31 112.5(8) . . ? O1 C32 H32A 109.1 . . ? C31 C32 H32A 109.1 . . ? O1 C32 H32B 109.1 . . ? C31 C32 H32B 109.1 . . ? H32A C32 H32B 107.8 . . ? O2 C33 C34 102.5(6) . . ? O2 C33 H33A 111.3 . . ? C34 C33 H33A 111.3 . . ? O2 C33 H33B 111.3 . . ? C34 C33 H33B 111.3 . . ? H33A C33 H33B 109.2 . . ? C35 C34 C33 102.1(6) . . ? C35 C34 H34A 111.3 . . ? C33 C34 H34A 111.3 . . ? C35 C34 H34B 111.3 . . ? C33 C34 H34B 111.3 . . ? H34A C34 H34B 109.2 . . ? C36 C35 C34 102.9(7) . . ? C36 C35 H35A 111.2 . . ? C34 C35 H35A 111.2 . . ? C36 C35 H35B 111.2 . . ? C34 C35 H35B 111.2 . . ? H35A C35 H35B 109.1 . . ? O2 C36 C35 108.0(7) . . ? O2 C36 H36A 110.1 . . ? C35 C36 H36A 110.1 . . ? O2 C36 H36B 110.1 . . ? C35 C36 H36B 110.1 . . ? H36A C36 H36B 108.4 . . ? 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 C2 N1 C1 N2 0.8(4) . . . . ? C8 N1 C1 N2 -179.9(3) . . . . ? C3 N2 C1 N1 -1.2(4) . . . . ? C4 N2 C1 N1 -174.8(3) . . . . ? C1 N1 C2 C3 -0.1(5) . . . . ? C8 N1 C2 C3 -179.4(3) . . . . ? N1 C2 C3 N2 -0.6(5) . . . . ? C1 N2 C3 C2 1.1(5) . . . . ? C4 N2 C3 C2 174.6(4) . . . . ? C1 N2 C4 N3 -114.9(4) . . . . ? C3 N2 C4 N3 72.6(5) . . . . ? C5 N3 C4 N2 -97.8(5) . . . . ? C7 N3 C4 N2 87.8(5) . . . . ? C6 N4 C5 N3 1.0(5) . . . . ? C20 N4 C5 N3 -175.7(4) . . . . ? C7 N3 C5 N4 -1.1(5) . . . . ? C4 N3 C5 N4 -176.3(3) . . . . ? C5 N4 C6 C7 -0.5(5) . . . . ? C20 N4 C6 C7 176.1(4) . . . . ? N4 C6 C7 N3 -0.1(5) . . . . ? C5 N3 C7 C6 0.7(5) . . . . ? C4 N3 C7 C6 175.8(4) . . . . ? C1 N1 C8 C9 93.4(5) . . . . ? C2 N1 C8 C9 -87.3(5) . . . . ? C1 N1 C8 C13 -90.2(5) . . . . ? C2 N1 C8 C13 89.1(5) . . . . ? C13 C8 C9 C10 -0.2(6) . . . . ? N1 C8 C9 C10 175.9(3) . . . . ? C13 C8 C9 C14 179.7(4) . . . . ? N1 C8 C9 C14 -4.1(5) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C14 C9 C10 C11 179.5(4) . . . . ? C9 C10 C11 C12 1.7(7) . . . . ? C10 C11 C12 C13 -1.9(7) . . . . ? C11 C12 C13 C8 1.0(6) . . . . ? C11 C12 C13 C17 -176.9(4) . . . . ? C9 C8 C13 C12 0.0(6) . . . . ? N1 C8 C13 C12 -176.1(3) . . . . ? C9 C8 C13 C17 177.9(4) . . . . ? N1 C8 C13 C17 1.8(5) . . . . ? C8 C9 C14 C15 121.7(4) . . . . ? C10 C9 C14 C15 -58.3(5) . . . . ? C8 C9 C14 C16 -114.0(4) . . . . ? C10 C9 C14 C16 65.9(5) . . . . ? C12 C13 C17 C18 -56.3(5) . . . . ? C8 C13 C17 C18 125.9(4) . . . . ? C12 C13 C17 C19 66.3(5) . . . . ? C8 C13 C17 C19 -111.6(4) . . . . ? C5 N4 C20 C21 -105.0(5) . . . . ? C6 N4 C20 C21 78.8(5) . . . . ? C5 N4 C20 C25 74.8(5) . . . . ? C6 N4 C20 C25 -101.3(5) . . . . ? C25 C20 C21 C22 0.2(7) . . . . ? N4 C20 C21 C22 180.0(4) . . . . ? C25 C20 C21 C26 -179.6(5) . . . . ? N4 C20 C21 C26 0.2(7) . . . . ? C20 C21 C22 C23 -0.2(7) . . . . ? C26 C21 C22 C23 179.7(5) . . . . ? C21 C22 C23 C24 0.4(7) . . . . ? C21 C22 C23 C27 -178.7(4) . . . . ? C22 C23 C24 C25 -0.6(7) . . . . ? C27 C23 C24 C25 178.5(4) . . . . ? C23 C24 C25 C20 0.6(7) . . . . ? C23 C24 C25 C28 178.8(5) . . . . ? C21 C20 C25 C24 -0.4(7) . . . . ? N4 C20 C25 C24 179.8(4) . . . . ? C21 C20 C25 C28 -178.6(4) . . . . ? N4 C20 C25 C28 1.5(6) . . . . ? C32 O1 C29 C30 -31.5(10) . . . . ? O1 C29 C30 C31 20.2(9) . . . . ? C29 C30 C31 C32 -2.7(12) . . . . ? C29 O1 C32 C31 32.2(14) . . . . ? C30 C31 C32 O1 -18.7(15) . . . . ? C36 O2 C33 C34 -25.1(7) . . . . ? O2 C33 C34 C35 37.7(7) . . . . ? C33 C34 C35 C36 -36.2(8) . . . . ? C33 O2 C36 C35 2.3(8) . . . . ? C34 C35 C36 O2 21.8(9) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 30.94 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.458 _refine_diff_density_min -2.004 _refine_diff_density_rms 0.126 data_d:\as31mt04 _database_code_depnum_ccdc_archive 'CCDC 913062' #TrackingRef 'compound 5 revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 I2 N4 O Pd S' _chemical_formula_weight 718.70 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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 10.1160(10) _cell_length_b 15.4080(13) _cell_length_c 15.4050(16) _cell_angle_alpha 90.00 _cell_angle_beta 103.568(5) _cell_angle_gamma 90.00 _cell_volume 2334.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 32102 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 27.19 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.045 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 3.547 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35655 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.19 _reflns_number_total 5126 _reflns_number_gt 4949 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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. Difference maps showed a disordered DMSO model related to inversion at S stom. This could not be suitably modelled and the refinement with a residual e- density of +2.96 is presented in the region of the low occupancy S atom. SADI was used to given acceptable S-C distances. ; _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^)+(0.0524P)^2^+32.2011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5126 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.072 _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 I1 I 0.19485(5) 0.84589(3) 0.54994(3) 0.03559(15) Uani 1 1 d . . . I2 I 0.57592(5) 0.88018(3) 0.65525(3) 0.03469(15) Uani 1 1 d . . . Pd1 Pd 0.42582(5) 0.76959(3) 0.54309(3) 0.02003(13) Uani 1 1 d . . . S1 S 1.1440(5) 0.5276(4) 0.7300(3) 0.1097(16) Uani 1 1 d D . . O1 O 1.0546(10) 0.5307(7) 0.6586(4) 0.091(4) Uani 1 1 d . . . N1 N 0.2240(5) 0.6394(4) 0.4289(4) 0.0244(11) Uani 1 1 d . . . N2 N 0.3770(5) 0.6895(4) 0.3673(3) 0.0214(10) Uani 1 1 d . . . N3 N 0.6086(5) 0.7003(4) 0.4397(3) 0.0214(10) Uani 1 1 d . . . N4 N 0.6959(5) 0.6674(4) 0.5756(3) 0.0212(10) Uani 1 1 d . . . C1 C 0.3307(6) 0.6943(4) 0.4424(4) 0.0229(12) Uani 1 1 d . . . C2 C 0.2047(7) 0.6011(5) 0.3444(5) 0.0322(15) Uani 1 1 d . . . H2 H 0.1361 0.5604 0.3187 0.039 Uiso 1 1 calc R . . C3 C 0.3016(7) 0.6328(5) 0.3065(4) 0.0272(13) Uani 1 1 d . . . H3 H 0.3152 0.6187 0.2491 0.033 Uiso 1 1 calc R . . C4 C 0.5051(6) 0.7304(5) 0.3627(4) 0.0235(13) Uani 1 1 d . . . H4A H 0.4966 0.7944 0.3644 0.028 Uiso 1 1 calc R . . H4B H 0.5302 0.7141 0.3066 0.028 Uiso 1 1 calc R . . C5 C 0.5908(6) 0.7100(4) 0.5229(4) 0.0218(12) Uani 1 1 d . . . C6 C 0.7790(7) 0.6307(5) 0.5248(4) 0.0257(13) Uani 1 1 d . . . H6 H 0.8594 0.5978 0.5465 0.031 Uiso 1 1 calc R . . C7 C 0.7225(6) 0.6510(5) 0.4385(4) 0.0248(13) Uani 1 1 d . . . H7 H 0.7546 0.6347 0.3876 0.030 Uiso 1 1 calc R . . C8 C 0.1435(8) 0.6162(6) 0.4924(5) 0.0366(17) Uani 1 1 d . . . H8A H 0.1885 0.5690 0.5307 0.055 Uiso 1 1 calc R . . H8B H 0.0529 0.5973 0.4599 0.055 Uiso 1 1 calc R . . H8C H 0.1349 0.6668 0.5292 0.055 Uiso 1 1 calc R . . C9 C 0.7186(6) 0.6548(4) 0.6709(4) 0.0208(12) Uani 1 1 d . . . C10 C 0.8281(7) 0.6975(5) 0.7271(4) 0.0273(14) Uani 1 1 d . . . C11 C 0.8496(7) 0.6821(5) 0.8185(4) 0.0280(14) Uani 1 1 d . . . H11 H 0.9226 0.7109 0.8580 0.034 Uiso 1 1 calc R . . C12 C 0.7679(7) 0.6258(4) 0.8539(4) 0.0245(13) Uani 1 1 d . . . C13 C 0.6600(7) 0.5846(4) 0.7949(4) 0.0228(12) Uani 1 1 d . . . H13 H 0.6032 0.5463 0.8182 0.027 Uiso 1 1 calc R . . C14 C 0.6333(6) 0.5980(4) 0.7029(4) 0.0207(12) Uani 1 1 d . . . C15 C 0.9196(8) 0.7564(6) 0.6908(5) 0.0402(19) Uani 1 1 d . . . H15A H 0.9849 0.7838 0.7404 0.060 Uiso 1 1 calc R . . H15B H 0.8651 0.8013 0.6538 0.060 Uiso 1 1 calc R . . H15C H 0.9687 0.7227 0.6545 0.060 Uiso 1 1 calc R . . C16 C 0.7961(8) 0.6082(6) 0.9530(4) 0.0333(16) Uani 1 1 d . . . H16A H 0.8633 0.5615 0.9685 0.050 Uiso 1 1 calc R . . H16B H 0.7116 0.5906 0.9689 0.050 Uiso 1 1 calc R . . H16C H 0.8315 0.6609 0.9859 0.050 Uiso 1 1 calc R . . C17 C 0.5158(7) 0.5532(5) 0.6416(4) 0.0272(13) Uani 1 1 d . . . H17A H 0.4832 0.5059 0.6737 0.041 Uiso 1 1 calc R . . H17B H 0.5453 0.5294 0.5902 0.041 Uiso 1 1 calc R . . H17C H 0.4421 0.5949 0.6207 0.041 Uiso 1 1 calc R . . C18 C 1.0815(18) 0.5030(12) 0.8247(10) 0.101(5) Uani 1 1 d D . . H18A H 1.0242 0.4511 0.8129 0.152 Uiso 1 1 calc R . . H18B H 1.0277 0.5519 0.8381 0.152 Uiso 1 1 calc R . . H18C H 1.1580 0.4923 0.8759 0.152 Uiso 1 1 calc R . . C19 C 1.2330(18) 0.6137(11) 0.7832(13) 0.116(7) Uani 1 1 d D . . H19A H 1.2836 0.6413 0.7437 0.174 Uiso 1 1 calc R . . H19B H 1.2967 0.5936 0.8376 0.174 Uiso 1 1 calc R . . H19C H 1.1698 0.6558 0.7990 0.174 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 I1 0.0317(3) 0.0435(3) 0.0294(2) -0.00446(19) 0.00262(18) 0.0090(2) I2 0.0361(3) 0.0404(3) 0.0303(2) -0.00814(19) 0.01319(19) -0.0071(2) Pd1 0.0207(2) 0.0265(2) 0.0130(2) 0.00059(17) 0.00416(16) -0.00009(17) S1 0.102(3) 0.150(4) 0.070(2) -0.002(3) 0.006(2) -0.026(3) O1 0.112(7) 0.135(8) 0.025(3) -0.012(4) 0.014(4) -0.089(7) N1 0.018(2) 0.034(3) 0.021(3) 0.000(2) 0.006(2) -0.004(2) N2 0.019(2) 0.031(3) 0.013(2) 0.003(2) 0.0006(19) -0.002(2) N3 0.018(2) 0.035(3) 0.011(2) 0.000(2) 0.0037(19) -0.001(2) N4 0.018(2) 0.032(3) 0.013(2) 0.001(2) 0.0040(18) -0.001(2) C1 0.020(3) 0.030(3) 0.019(3) 0.003(2) 0.003(2) 0.000(2) C2 0.025(3) 0.045(4) 0.025(3) -0.008(3) 0.003(3) -0.005(3) C3 0.026(3) 0.035(3) 0.019(3) -0.003(3) 0.000(2) 0.000(3) C4 0.021(3) 0.037(4) 0.012(3) 0.005(2) 0.002(2) -0.004(3) C5 0.023(3) 0.028(3) 0.016(3) 0.002(2) 0.006(2) -0.005(2) C6 0.021(3) 0.037(4) 0.021(3) 0.001(3) 0.008(2) -0.003(3) C7 0.017(3) 0.041(4) 0.017(3) 0.000(3) 0.007(2) -0.003(3) C8 0.027(3) 0.052(5) 0.035(4) -0.006(3) 0.016(3) -0.011(3) C9 0.020(3) 0.032(3) 0.010(2) 0.001(2) 0.003(2) -0.003(2) C10 0.024(3) 0.039(4) 0.017(3) 0.003(3) 0.000(2) -0.010(3) C11 0.026(3) 0.038(4) 0.017(3) 0.000(3) -0.002(2) -0.005(3) C12 0.028(3) 0.031(3) 0.014(3) 0.000(2) 0.003(2) 0.006(3) C13 0.025(3) 0.027(3) 0.019(3) 0.002(2) 0.010(2) 0.002(2) C14 0.019(3) 0.023(3) 0.019(3) 0.000(2) 0.001(2) 0.000(2) C15 0.035(4) 0.054(5) 0.028(4) 0.005(3) 0.003(3) -0.020(4) C16 0.039(4) 0.048(4) 0.013(3) 0.001(3) 0.006(3) 0.006(3) C17 0.023(3) 0.033(3) 0.023(3) 0.002(3) 0.000(2) -0.007(3) C18 0.109(12) 0.120(13) 0.077(9) 0.031(9) 0.028(9) 0.036(11) C19 0.094(11) 0.098(12) 0.127(14) -0.054(11) -0.031(10) -0.008(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 5.3815 (0.0303) x + 11.5125 (0.0382) y - 4.0436 (0.0524) z = 4.4238 (0.0408) * 0.0011 (0.0039) C1 * -0.0020 (0.0043) N1 * 0.0002 (0.0040) N2 * 0.0021 (0.0045) C2 * -0.0014 (0.0044) C3 Rms deviation of fitted atoms = 0.0015 2.5655 (0.0107) x + 9.9181 (0.0155) y - 11.7291 (0.0131) z = 2.4575 (0.0201) Angle to previous plane (with approximate esd) = 50.68 ( 0.23 ) * -0.1022 (0.0020) Pd1 * 0.0882 (0.0031) C1 * -0.0321 (0.0030) C5 * -0.0182 (0.0021) I1 * 0.0643 (0.0021) I2 1.8282 (0.0080) C4 Rms deviation of fitted atoms = 0.0689 5.4697 (0.0294) x + 12.8674 (0.0292) y - 0.4390 (0.0517) z = 12.1417 (0.0220) Angle to previous plane (with approximate esd) = 53.01 ( 0.21 ) * -0.0033 (0.0038) C5 * 0.0057 (0.0040) N3 * -0.0004 (0.0039) N4 * 0.0038 (0.0041) C6 * -0.0058 (0.0041) C7 Rms deviation of fitted atoms = 0.0043 2.6468 (0.0316) x + 10.9715 (0.0326) y - 10.7024 (0.0340) z = 3.7582 (0.0441) Angle to previous plane (with approximate esd) = 47.92 ( 0.27 ) * 0.0000 (0.0001) Pd1 * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C5 0.1526 (0.0083) I1 0.4103 (0.0085) I2 Rms deviation of fitted atoms = 0.0000 ; 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 I1 Pd1 2.6397(7) . ? I2 Pd1 2.6389(7) . ? Pd1 C5 1.992(7) . ? Pd1 C1 1.994(7) . ? S1 O1 1.251(9) . ? S1 C19 1.701(13) . ? S1 C18 1.762(13) . ? N1 C1 1.349(8) . ? N1 C2 1.401(9) . ? N1 C8 1.456(9) . ? N2 C1 1.349(8) . ? N2 C3 1.374(8) . ? N2 C4 1.457(8) . ? N3 C5 1.343(8) . ? N3 C7 1.384(8) . ? N3 C4 1.461(8) . ? N4 C5 1.348(8) . ? N4 C6 1.395(8) . ? N4 C9 1.445(7) . ? C2 C3 1.346(10) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.355(9) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.398(9) . ? C9 C10 1.399(9) . ? C10 C11 1.393(9) . ? C10 C15 1.495(10) . ? C11 C12 1.395(10) . ? C11 H11 0.9500 . ? C12 C13 1.398(9) . ? C12 C16 1.510(8) . ? C13 C14 1.394(8) . ? C13 H13 0.9500 . ? C14 C17 1.503(9) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Pd1 C1 83.1(3) . . ? C5 Pd1 I2 91.45(18) . . ? C1 Pd1 I2 169.54(18) . . ? C5 Pd1 I1 173.35(18) . . ? C1 Pd1 I1 91.14(19) . . ? I2 Pd1 I1 93.73(2) . . ? O1 S1 C19 125.9(9) . . ? O1 S1 C18 114.2(8) . . ? C19 S1 C18 91.2(11) . . ? C1 N1 C2 109.9(6) . . ? C1 N1 C8 127.1(6) . . ? C2 N1 C8 122.8(6) . . ? C1 N2 C3 111.8(6) . . ? C1 N2 C4 120.6(5) . . ? C3 N2 C4 126.9(5) . . ? C5 N3 C7 111.8(5) . . ? C5 N3 C4 120.5(5) . . ? C7 N3 C4 127.2(5) . . ? C5 N4 C6 110.7(5) . . ? C5 N4 C9 126.4(5) . . ? C6 N4 C9 122.9(5) . . ? N1 C1 N2 105.1(5) . . ? N1 C1 Pd1 135.0(5) . . ? N2 C1 Pd1 119.9(5) . . ? C3 C2 N1 107.1(6) . . ? C3 C2 H2 126.5 . . ? N1 C2 H2 126.5 . . ? C2 C3 N2 106.2(6) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N2 C4 N3 107.5(5) . . ? N2 C4 H4A 110.2 . . ? N3 C4 H4A 110.2 . . ? N2 C4 H4B 110.2 . . ? N3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? N3 C5 N4 104.9(5) . . ? N3 C5 Pd1 120.4(5) . . ? N4 C5 Pd1 134.5(4) . . ? C7 C6 N4 106.6(6) . . ? C7 C6 H6 126.7 . . ? N4 C6 H6 126.7 . . ? C6 C7 N3 106.0(5) . . ? C6 C7 H7 127.0 . . ? N3 C7 H7 127.0 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 122.7(6) . . ? C14 C9 N4 118.6(5) . . ? C10 C9 N4 118.7(5) . . ? C11 C10 C9 117.3(6) . . ? C11 C10 C15 121.1(6) . . ? C9 C10 C15 121.6(6) . . ? C10 C11 C12 122.3(6) . . ? C10 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C11 C12 C13 118.1(6) . . ? C11 C12 C16 121.3(6) . . ? C13 C12 C16 120.6(6) . . ? C14 C13 C12 122.0(6) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C9 117.6(6) . . ? C13 C14 C17 120.5(6) . . ? C9 C14 C17 121.9(5) . . ? 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 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? S1 C19 H19A 109.5 . . ? S1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? S1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C2 N1 C1 N2 -0.3(8) . . . . ? C8 N1 C1 N2 175.5(7) . . . . ? C2 N1 C1 Pd1 -177.9(6) . . . . ? C8 N1 C1 Pd1 -2.1(12) . . . . ? C3 N2 C1 N1 0.1(7) . . . . ? C4 N2 C1 N1 -170.7(6) . . . . ? C3 N2 C1 Pd1 178.2(5) . . . . ? C4 N2 C1 Pd1 7.4(8) . . . . ? C5 Pd1 C1 N1 129.0(7) . . . . ? I2 Pd1 C1 N1 -172.0(6) . . . . ? I1 Pd1 C1 N1 -54.3(7) . . . . ? C5 Pd1 C1 N2 -48.3(5) . . . . ? I2 Pd1 C1 N2 10.6(15) . . . . ? I1 Pd1 C1 N2 128.3(5) . . . . ? C1 N1 C2 C3 0.4(8) . . . . ? C8 N1 C2 C3 -175.7(7) . . . . ? N1 C2 C3 N2 -0.3(8) . . . . ? C1 N2 C3 C2 0.2(8) . . . . ? C4 N2 C3 C2 170.2(6) . . . . ? C1 N2 C4 N3 52.1(8) . . . . ? C3 N2 C4 N3 -117.2(7) . . . . ? C5 N3 C4 N2 -55.2(8) . . . . ? C7 N3 C4 N2 116.1(7) . . . . ? C7 N3 C5 N4 0.9(7) . . . . ? C4 N3 C5 N4 173.4(6) . . . . ? C7 N3 C5 Pd1 -174.7(4) . . . . ? C4 N3 C5 Pd1 -2.2(8) . . . . ? C6 N4 C5 N3 -0.3(7) . . . . ? C9 N4 C5 N3 -176.4(6) . . . . ? C6 N4 C5 Pd1 174.4(5) . . . . ? C9 N4 C5 Pd1 -1.8(10) . . . . ? C1 Pd1 C5 N3 45.8(5) . . . . ? I2 Pd1 C5 N3 -125.3(5) . . . . ? I1 Pd1 C5 N3 16(2) . . . . ? C1 Pd1 C5 N4 -128.3(7) . . . . ? I2 Pd1 C5 N4 60.7(7) . . . . ? I1 Pd1 C5 N4 -158.2(11) . . . . ? C5 N4 C6 C7 -0.4(8) . . . . ? C9 N4 C6 C7 175.9(6) . . . . ? N4 C6 C7 N3 0.9(7) . . . . ? C5 N3 C7 C6 -1.2(8) . . . . ? C4 N3 C7 C6 -173.0(6) . . . . ? C5 N4 C9 C14 71.0(9) . . . . ? C6 N4 C9 C14 -104.7(7) . . . . ? C5 N4 C9 C10 -111.3(8) . . . . ? C6 N4 C9 C10 72.9(9) . . . . ? C14 C9 C10 C11 -0.6(11) . . . . ? N4 C9 C10 C11 -178.2(6) . . . . ? C14 C9 C10 C15 178.6(7) . . . . ? N4 C9 C10 C15 1.1(11) . . . . ? C9 C10 C11 C12 0.9(11) . . . . ? C15 C10 C11 C12 -178.4(8) . . . . ? C10 C11 C12 C13 -0.7(11) . . . . ? C10 C11 C12 C16 178.1(7) . . . . ? C11 C12 C13 C14 0.3(10) . . . . ? C16 C12 C13 C14 -178.5(6) . . . . ? C12 C13 C14 C9 -0.1(10) . . . . ? C12 C13 C14 C17 -179.5(6) . . . . ? C10 C9 C14 C13 0.3(10) . . . . ? N4 C9 C14 C13 177.8(6) . . . . ? C10 C9 C14 C17 179.7(7) . . . . ? N4 C9 C14 C17 -2.8(10) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.19 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.963 _refine_diff_density_min -2.735 _refine_diff_density_rms 0.197 data_d:\31mt02a _database_code_depnum_ccdc_archive 'CCDC 913063' #TrackingRef 'web_deposit_cif_file_2_michaelgardiner_1354099828.compound 5a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H52 Cl2 I2 N8 O2 Pd2' _chemical_formula_weight 1190.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 18.854(2) _cell_length_b 19.529(2) _cell_length_c 12.140(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4469.9(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 40405 _cell_measurement_theta_min 1.98 _cell_measurement_theta_max 27.16 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 2.347 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 68326 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.16 _reflns_number_total 4983 _reflns_number_gt 4100 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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. Disorder of the Cl ligands in the palladate counter anion across the mirror plane was apparent, but this could not be effectively modelled. Thus the refinement model shows large thermal motion of this atom with the highest residual electron density being associated with this atom. ; _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^)+(0.1167P)^2^+34.6926P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4983 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1989 _refine_ls_wR_factor_gt 0.1868 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 I1 I 0.37907(4) 0.2500 0.03073(8) 0.0481(2) Uani 1 2 d S . . I2 I 0.10075(4) 0.2500 0.05434(6) 0.0345(2) Uani 1 2 d S . . Pd1 Pd 0.0000 0.5000 0.0000 0.0273(2) Uani 1 2 d S . . Pd2 Pd 0.24017(4) 0.2500 0.04007(7) 0.0334(2) Uani 1 2 d S . . Cl1 Cl 0.2336(3) 0.2500 -0.1651(7) 0.261(9) Uani 1 2 d S . . Cl2 Cl 0.2478(3) 0.2500 0.2406(9) 0.321(13) Uani 1 2 d S . . O18 O 0.1102(7) 0.2500 0.6788(14) 0.098(4) Uani 1 2 d S . . O19 O 0.0704(8) 0.2500 0.4729(12) 0.088(4) Uani 1 2 d S . . N1 N -0.0958(3) 0.4236(3) 0.1703(5) 0.0327(13) Uani 1 1 d . . . N2 N -0.1055(3) 0.5325(3) 0.1750(5) 0.0322(13) Uani 1 1 d . . . N3 N -0.0117(3) 0.6124(3) 0.1654(5) 0.0335(13) Uani 1 1 d . . . N4 N 0.0985(3) 0.5881(3) 0.1455(5) 0.0320(12) Uani 1 1 d . . . C1 C -0.0721(4) 0.4808(4) 0.1208(6) 0.0304(14) Uani 1 1 d . . . C2 C -0.1449(4) 0.4392(4) 0.2538(7) 0.0415(17) Uani 1 1 d . . . H2 H -0.1694 0.4076 0.2996 0.050 Uiso 1 1 calc R . . C3 C -0.1502(4) 0.5084(4) 0.2559(7) 0.0405(17) Uani 1 1 d . . . H3 H -0.1790 0.5350 0.3037 0.049 Uiso 1 1 calc R . . C4 C -0.0876(4) 0.6046(4) 0.1538(7) 0.0370(16) Uani 1 1 d . . . H4A H -0.1026 0.6176 0.0785 0.044 Uiso 1 1 calc R . . H4B H -0.1126 0.6345 0.2070 0.044 Uiso 1 1 calc R . . C5 C 0.0338(4) 0.5730(4) 0.1078(6) 0.0309(14) Uani 1 1 d . . . C6 C 0.0943(4) 0.6390(4) 0.2282(6) 0.0362(16) Uani 1 1 d . . . H6 H 0.1327 0.6590 0.2673 0.043 Uiso 1 1 calc R . . C7 C 0.0249(5) 0.6534(4) 0.2404(7) 0.0396(17) Uani 1 1 d . . . H7 H 0.0048 0.6853 0.2905 0.048 Uiso 1 1 calc R . . C8 C -0.0708(4) 0.3536(3) 0.1494(7) 0.0341(15) Uani 1 1 d . . . H8A H -0.0532 0.3503 0.0736 0.051 Uiso 1 1 calc R . . H8B H -0.1100 0.3213 0.1598 0.051 Uiso 1 1 calc R . . H8C H -0.0324 0.3425 0.2008 0.051 Uiso 1 1 calc R . . C9 C 0.1608(4) 0.5542(3) 0.1045(6) 0.0304(14) Uani 1 1 d . . . C10 C 0.2099(4) 0.5919(4) 0.0439(6) 0.0353(16) Uani 1 1 d . . . C11 C 0.2634(4) 0.5556(4) -0.0112(7) 0.0386(17) Uani 1 1 d . . . H11 H 0.2972 0.5799 -0.0540 0.046 Uiso 1 1 calc R . . C12 C 0.2678(4) 0.4848(4) -0.0044(7) 0.0390(17) Uani 1 1 d . . . C13 C 0.2210(4) 0.4491(4) 0.0637(6) 0.0333(15) Uani 1 1 d . . . H13 H 0.2264 0.4010 0.0722 0.040 Uiso 1 1 calc R . . C14 C 0.1665(4) 0.4827(4) 0.1194(6) 0.0317(14) Uani 1 1 d . . . C15 C 0.2084(5) 0.6684(4) 0.0365(7) 0.0420(18) Uani 1 1 d . . . H15A H 0.1592 0.6840 0.0306 0.063 Uiso 1 1 calc R . . H15B H 0.2350 0.6832 -0.0286 0.063 Uiso 1 1 calc R . . H15C H 0.2301 0.6880 0.1028 0.063 Uiso 1 1 calc R . . C16 C 0.3238(5) 0.4469(5) -0.0678(8) 0.051(2) Uani 1 1 d . . . H16A H 0.3242 0.3988 -0.0448 0.076 Uiso 1 1 calc R . . H16B H 0.3703 0.4674 -0.0531 0.076 Uiso 1 1 calc R . . H16C H 0.3134 0.4497 -0.1467 0.076 Uiso 1 1 calc R . . C17 C 0.1184(4) 0.4416(4) 0.1918(7) 0.0358(16) Uani 1 1 d . . . H17A H 0.0800 0.4221 0.1473 0.054 Uiso 1 1 calc R . . H17B H 0.0982 0.4713 0.2488 0.054 Uiso 1 1 calc R . . H17C H 0.1454 0.4046 0.2265 0.054 Uiso 1 1 calc R . . C20 C 0.0765(9) 0.3088(9) 0.4071(13) 0.098(5) Uani 1 1 d . . . H20A H 0.0452 0.3049 0.3419 0.117 Uiso 1 1 calc R . . H20B H 0.1260 0.3141 0.3812 0.117 Uiso 1 1 calc R . . C22 C 0.0547(11) 0.3716(11) 0.4772(16) 0.124(7) Uani 1 1 d . . . H22A H 0.0059 0.3847 0.4591 0.185 Uiso 1 1 calc R . . H22B H 0.0866 0.4099 0.4613 0.185 Uiso 1 1 calc R . . H22C H 0.0577 0.3598 0.5555 0.185 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 I1 0.0336(4) 0.0445(5) 0.0661(5) 0.000 -0.0044(3) 0.000 I2 0.0340(4) 0.0246(3) 0.0448(4) 0.000 0.0024(3) 0.000 Pd1 0.0320(4) 0.0207(4) 0.0292(4) 0.0018(3) 0.0012(3) 0.0024(3) Pd2 0.0328(4) 0.0285(4) 0.0390(4) 0.000 -0.0019(3) 0.000 Cl1 0.032(2) 0.63(3) 0.121(6) 0.000 0.017(3) 0.000 Cl2 0.047(3) 0.78(4) 0.135(8) 0.000 -0.003(4) 0.000 O18 0.078(9) 0.107(11) 0.109(11) 0.000 -0.001(8) 0.000 O19 0.101(10) 0.071(8) 0.092(9) 0.000 0.028(8) 0.000 N1 0.039(3) 0.026(3) 0.032(3) 0.002(2) 0.005(3) 0.006(2) N2 0.038(3) 0.028(3) 0.031(3) 0.005(2) 0.005(2) 0.007(2) N3 0.045(3) 0.017(3) 0.038(3) -0.001(2) 0.002(3) 0.004(2) N4 0.039(3) 0.020(3) 0.037(3) 0.000(2) -0.003(3) 0.001(2) C1 0.033(3) 0.024(3) 0.034(4) 0.005(3) 0.000(3) 0.004(3) C2 0.040(4) 0.047(5) 0.038(4) 0.008(3) 0.011(3) 0.003(3) C3 0.042(4) 0.038(4) 0.041(4) 0.004(3) 0.007(3) 0.009(3) C4 0.044(4) 0.023(3) 0.044(4) 0.004(3) 0.005(3) 0.007(3) C5 0.036(4) 0.024(3) 0.032(3) 0.004(3) 0.000(3) 0.002(3) C6 0.048(4) 0.022(3) 0.039(4) -0.003(3) -0.002(3) 0.002(3) C7 0.056(5) 0.023(4) 0.040(4) -0.006(3) -0.003(3) 0.004(3) C8 0.044(4) 0.015(3) 0.043(4) 0.004(3) 0.003(3) 0.001(3) C9 0.038(4) 0.016(3) 0.036(4) -0.002(3) -0.005(3) -0.001(3) C10 0.041(4) 0.027(4) 0.038(4) 0.003(3) -0.008(3) -0.004(3) C11 0.039(4) 0.034(4) 0.043(4) 0.004(3) 0.002(3) -0.004(3) C12 0.039(4) 0.030(4) 0.048(5) 0.001(3) -0.003(3) -0.001(3) C13 0.040(4) 0.018(3) 0.042(4) -0.002(3) -0.009(3) 0.001(3) C14 0.039(4) 0.022(3) 0.034(4) 0.000(3) -0.005(3) 0.002(3) C15 0.051(5) 0.025(4) 0.051(5) 0.008(3) -0.003(4) -0.010(3) C16 0.054(5) 0.040(5) 0.058(5) -0.002(4) 0.014(4) 0.005(4) C17 0.045(4) 0.021(3) 0.041(4) 0.006(3) -0.004(3) -0.002(3) C20 0.092(10) 0.126(13) 0.075(8) 0.035(9) 0.002(7) -0.028(9) C22 0.130(17) 0.117(15) 0.124(14) 0.001(12) 0.034(13) -0.046(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 7.8190 (0.0663) x + 4.9767 (0.1258) y - 10.6048 (0.0418) z = 1.0577 (0.0772) * 0.6193 (0.0064) C1 * -0.4452 (0.0044) N1 * 0.3285 (0.0064) N2 * -0.4338 (0.0059) C2 * -0.0688 (0.0059) C3 Rms deviation of fitted atoms = 0.4201 - 11.8183 (0.0525) x + 12.8934 (0.0523) y - 5.0229 (0.0356) z = 6.4467 (0.0262) Angle to previous plane (with approximate esd) = 37.85 ( 0.48 ) * 0.0000 (0.0000) Pd1 * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C5 * 0.0000 (0.0000) C1_$1 * 0.0000 (0.0000) C5_$1 1.6084 (0.0117) C4 Rms deviation of fitted atoms = 0.0000 - 5.3007 (0.1127) x + 7.6901 (0.0924) y - 10.6244 (0.0482) z = 2.4324 (0.0618) Angle to previous plane (with approximate esd) = 37.03 ( 0.50 ) * 0.6476 (0.0067) C5 * 0.3615 (0.0066) N3 * -0.4753 (0.0045) N4 * -0.4406 (0.0055) C6 * -0.0932 (0.0060) C7 Rms deviation of fitted atoms = 0.4424 ; 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 I1 Pd2 2.6212(11) . ? I2 Pd2 2.6344(11) . ? Pd1 C1 2.035(7) . ? Pd1 C1 2.035(7) 5_565 ? Pd1 C5 2.037(7) 5_565 ? Pd1 C5 2.037(7) . ? Pd2 Cl2 2.438(11) . ? Pd2 Cl1 2.494(9) . ? O19 C20 1.404(16) 8_565 ? O19 C20 1.404(16) . ? N1 C1 1.344(9) . ? N1 C2 1.405(9) . ? N1 C8 1.469(9) . ? N2 C1 1.360(9) . ? N2 C3 1.377(10) . ? N2 C4 1.469(9) . ? N3 C5 1.348(9) . ? N3 C7 1.395(10) . ? N3 C4 1.447(10) . ? N4 C5 1.337(9) . ? N4 C6 1.415(9) . ? N4 C9 1.437(9) . ? C2 C3 1.355(11) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.345(12) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.393(11) . ? C9 C14 1.412(10) . ? C10 C11 1.402(12) . ? C10 C15 1.497(10) . ? C11 C12 1.387(12) . ? C11 H11 0.9500 . ? C12 C13 1.395(12) . ? C12 C16 1.501(12) . ? C13 C14 1.394(11) . ? C13 H13 0.9500 . ? C14 C17 1.497(10) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C20 C22 1.55(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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(4) . 5_565 ? C1 Pd1 C5 97.2(3) . 5_565 ? C1 Pd1 C5 82.8(3) 5_565 5_565 ? C1 Pd1 C5 82.8(3) . . ? C1 Pd1 C5 97.2(3) 5_565 . ? C5 Pd1 C5 180.0(4) 5_565 . ? Cl2 Pd2 Cl1 179.5(2) . . ? Cl2 Pd2 I1 89.11(15) . . ? Cl1 Pd2 I1 90.39(12) . . ? Cl2 Pd2 I2 89.60(15) . . ? Cl1 Pd2 I2 90.90(12) . . ? I1 Pd2 I2 178.71(4) . . ? C20 O19 C20 109.8(18) 8_565 . ? C1 N1 C2 111.2(6) . . ? C1 N1 C8 126.0(6) . . ? C2 N1 C8 122.6(6) . . ? C1 N2 C3 111.9(6) . . ? C1 N2 C4 121.4(6) . . ? C3 N2 C4 126.4(6) . . ? C5 N3 C7 110.6(7) . . ? C5 N3 C4 121.2(6) . . ? C7 N3 C4 127.9(7) . . ? C5 N4 C6 110.3(6) . . ? C5 N4 C9 121.7(6) . . ? C6 N4 C9 128.0(6) . . ? N1 C1 N2 104.3(6) . . ? N1 C1 Pd1 134.2(5) . . ? N2 C1 Pd1 121.3(5) . . ? C3 C2 N1 106.1(7) . . ? C3 C2 H2 126.9 . . ? N1 C2 H2 126.9 . . ? C2 C3 N2 106.5(7) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N3 C4 N2 108.1(6) . . ? N3 C4 H4A 110.1 . . ? N2 C4 H4A 110.1 . . ? N3 C4 H4B 110.1 . . ? N2 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N4 C5 N3 106.1(6) . . ? N4 C5 Pd1 131.3(5) . . ? N3 C5 Pd1 122.3(5) . . ? C7 C6 N4 106.3(7) . . ? C7 C6 H6 126.9 . . ? N4 C6 H6 126.9 . . ? C6 C7 N3 106.8(7) . . ? C6 C7 H7 126.6 . . ? N3 C7 H7 126.6 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 122.6(7) . . ? C10 C9 N4 118.9(6) . . ? C14 C9 N4 118.3(6) . . ? C9 C10 C11 117.6(7) . . ? C9 C10 C15 123.1(8) . . ? C11 C10 C15 119.4(7) . . ? C12 C11 C10 121.3(8) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.7(8) . . ? C11 C12 C16 120.2(8) . . ? C13 C12 C16 120.1(8) . . ? C14 C13 C12 121.2(7) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C9 117.4(7) . . ? C13 C14 C17 118.6(6) . . ? C9 C14 C17 124.0(7) . . ? 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 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O19 C20 C22 108.2(13) . . ? O19 C20 H20A 110.1 . . ? C22 C20 H20A 110.1 . . ? O19 C20 H20B 110.1 . . ? C22 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 C2 N1 C1 N2 1.1(8) . . . . ? C8 N1 C1 N2 -173.8(7) . . . . ? C2 N1 C1 Pd1 177.5(6) . . . . ? C8 N1 C1 Pd1 2.5(12) . . . . ? C3 N2 C1 N1 -1.0(8) . . . . ? C4 N2 C1 N1 173.0(6) . . . . ? C3 N2 C1 Pd1 -177.9(5) . . . . ? C4 N2 C1 Pd1 -4.0(9) . . . . ? C1 Pd1 C1 N1 5(14) 5_565 . . . ? C5 Pd1 C1 N1 47.0(8) 5_565 . . . ? C5 Pd1 C1 N1 -133.0(8) . . . . ? C1 Pd1 C1 N2 -179(100) 5_565 . . . ? C5 Pd1 C1 N2 -137.2(6) 5_565 . . . ? C5 Pd1 C1 N2 42.8(6) . . . . ? C1 N1 C2 C3 -0.9(9) . . . . ? C8 N1 C2 C3 174.3(7) . . . . ? N1 C2 C3 N2 0.3(9) . . . . ? C1 N2 C3 C2 0.4(9) . . . . ? C4 N2 C3 C2 -173.1(7) . . . . ? C5 N3 C4 N2 54.5(9) . . . . ? C7 N3 C4 N2 -118.4(7) . . . . ? C1 N2 C4 N3 -52.5(9) . . . . ? C3 N2 C4 N3 120.5(8) . . . . ? C6 N4 C5 N3 -0.7(8) . . . . ? C9 N4 C5 N3 178.3(6) . . . . ? C6 N4 C5 Pd1 -174.0(5) . . . . ? C9 N4 C5 Pd1 5.0(10) . . . . ? C7 N3 C5 N4 0.3(8) . . . . ? C4 N3 C5 N4 -173.8(6) . . . . ? C7 N3 C5 Pd1 174.3(5) . . . . ? C4 N3 C5 Pd1 0.3(9) . . . . ? C1 Pd1 C5 N4 130.8(7) . . . . ? C1 Pd1 C5 N4 -49.2(7) 5_565 . . . ? C5 Pd1 C5 N4 0.0(2) 5_565 . . . ? C1 Pd1 C5 N3 -41.6(6) . . . . ? C1 Pd1 C5 N3 138.4(6) 5_565 . . . ? C5 Pd1 C5 N3 0.0(10) 5_565 . . . ? C5 N4 C6 C7 0.9(8) . . . . ? C9 N4 C6 C7 -178.1(7) . . . . ? N4 C6 C7 N3 -0.7(8) . . . . ? C5 N3 C7 C6 0.3(9) . . . . ? C4 N3 C7 C6 173.8(7) . . . . ? C5 N4 C9 C10 112.8(8) . . . . ? C6 N4 C9 C10 -68.3(10) . . . . ? C5 N4 C9 C14 -61.8(9) . . . . ? C6 N4 C9 C14 117.1(8) . . . . ? C14 C9 C10 C11 5.3(11) . . . . ? N4 C9 C10 C11 -169.0(7) . . . . ? C14 C9 C10 C15 -173.9(7) . . . . ? N4 C9 C10 C15 11.7(11) . . . . ? C9 C10 C11 C12 -0.9(12) . . . . ? C15 C10 C11 C12 178.4(8) . . . . ? C10 C11 C12 C13 -3.9(13) . . . . ? C10 C11 C12 C16 177.6(8) . . . . ? C11 C12 C13 C14 4.4(12) . . . . ? C16 C12 C13 C14 -177.0(8) . . . . ? C12 C13 C14 C9 -0.2(11) . . . . ? C12 C13 C14 C17 -179.6(7) . . . . ? C10 C9 C14 C13 -4.8(11) . . . . ? N4 C9 C14 C13 169.6(6) . . . . ? C10 C9 C14 C17 174.5(7) . . . . ? N4 C9 C14 C17 -11.1(11) . . . . ? C20 O19 C20 C22 168.8(11) 8_565 . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 4.642 _refine_diff_density_min -2.525 _refine_diff_density_rms 0.233 data_d:\as31ch42 _database_code_depnum_ccdc_archive 'CCDC 913064' #TrackingRef 'compound 6 revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H38 Cl6 N4 Pd' _chemical_formula_weight 773.74 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 17.8530(16) _cell_length_b 12.240(2) _cell_length_c 15.180(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.862(8) _cell_angle_gamma 90.00 _cell_volume 3315.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 33188 _cell_measurement_theta_min 1.14 _cell_measurement_theta_max 27.13 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 1.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49147 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 27.13 _reflns_number_total 6716 _reflns_number_gt 5438 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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. DCM molecules had relatively high apparent thermal motion and required the use of SADI to give adequate C-Cl distances. ; _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^)+(0.1843P)^2^+12.9847P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6716 _refine_ls_number_parameters 374 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.2755 _refine_ls_wR_factor_gt 0.2597 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.051 _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 0.26671(3) 0.69531(4) 0.47682(3) 0.0364(3) Uani 1 1 d . . . Cl1 Cl 0.36006(9) 0.58846(18) 0.56884(9) 0.0437(5) Uani 1 1 d . . . Cl2 Cl 0.17269(9) 0.56909(16) 0.52761(10) 0.0413(5) Uani 1 1 d . . . Cl5 Cl 0.2879(6) 1.0855(6) 0.2913(5) 0.181(3) Uani 1 1 d D . . Cl6 Cl 0.3331(8) 1.2258(6) 0.1605(5) 0.239(6) Uani 1 1 d D . . Cl7 Cl 0.2298(5) 1.0757(7) 0.8151(4) 0.167(3) Uani 1 1 d D . . Cl8 Cl 0.2414(5) 1.2436(9) 0.9494(12) 0.305(9) Uani 1 1 d D . . N1 N 0.1250(4) 0.8065(5) 0.3936(4) 0.0380(13) Uani 1 1 d . . . N2 N 0.2192(4) 0.7975(5) 0.3093(4) 0.0402(13) Uani 1 1 d . . . N3 N 0.3492(4) 0.8060(6) 0.3383(5) 0.0461(15) Uani 1 1 d . . . N4 N 0.4079(4) 0.8424(7) 0.4600(4) 0.0502(16) Uani 1 1 d . . . C1 C 0.1955(4) 0.7675(6) 0.3902(4) 0.0385(14) Uani 1 1 d . . . C2 C 0.1050(5) 0.8610(6) 0.3153(5) 0.0440(16) Uani 1 1 d . . . H2 H 0.0584 0.8953 0.3016 0.053 Uiso 1 1 calc R . . C3 C 0.1647(5) 0.8556(7) 0.2626(5) 0.0450(16) Uani 1 1 d . . . H3 H 0.1684 0.8856 0.2052 0.054 Uiso 1 1 calc R . . C4 C 0.2920(5) 0.7652(7) 0.2770(5) 0.0448(16) Uani 1 1 d . . . H4A H 0.2952 0.6846 0.2728 0.054 Uiso 1 1 calc R . . H4B H 0.2991 0.7963 0.2176 0.054 Uiso 1 1 calc R . . C5 C 0.3474(4) 0.7876(6) 0.4267(5) 0.0406(15) Uani 1 1 d . . . C6 C 0.4450(6) 0.8935(9) 0.3929(6) 0.058(2) Uani 1 1 d . . . H6 H 0.4879 0.9390 0.4007 0.069 Uiso 1 1 calc R . . C7 C 0.4116(5) 0.8693(9) 0.3162(6) 0.058(2) Uani 1 1 d . . . H7 H 0.4264 0.8901 0.2590 0.070 Uiso 1 1 calc R . . C8 C 0.0707(4) 0.7871(6) 0.4594(5) 0.0396(15) Uani 1 1 d . . . C9 C 0.0109(5) 0.7140(6) 0.4398(5) 0.0419(16) Uani 1 1 d . . . C10 C -0.0401(5) 0.6946(6) 0.5038(6) 0.0466(17) Uani 1 1 d . . . H10 H -0.0792 0.6433 0.4924 0.056 Uiso 1 1 calc R . . C11 C -0.0360(5) 0.7479(7) 0.5848(5) 0.0483(17) Uani 1 1 d . . . H11 H -0.0723 0.7331 0.6276 0.058 Uiso 1 1 calc R . . C12 C 0.0196(5) 0.8207(6) 0.6029(5) 0.0460(17) Uani 1 1 d . . . H12 H 0.0215 0.8574 0.6581 0.055 Uiso 1 1 calc R . . C13 C 0.0755(4) 0.8429(6) 0.5401(5) 0.0384(14) Uani 1 1 d . . . C14 C 0.0033(5) 0.6529(7) 0.3522(5) 0.0444(16) Uani 1 1 d . . . H14 H 0.0411 0.6838 0.3119 0.053 Uiso 1 1 calc R . . C15 C 0.0185(6) 0.5338(8) 0.3619(6) 0.057(2) Uani 1 1 d . . . H15A H 0.0687 0.5230 0.3883 0.086 Uiso 1 1 calc R . . H15B H 0.0155 0.4990 0.3037 0.086 Uiso 1 1 calc R . . H15C H -0.0188 0.5011 0.3998 0.086 Uiso 1 1 calc R . . C16 C -0.0745(5) 0.6723(9) 0.3100(6) 0.055(2) Uani 1 1 d . . . H16A H -0.0835 0.7510 0.3044 0.083 Uiso 1 1 calc R . . H16B H -0.1126 0.6398 0.3470 0.083 Uiso 1 1 calc R . . H16C H -0.0773 0.6385 0.2514 0.083 Uiso 1 1 calc R . . C17 C 0.1374(4) 0.9267(6) 0.5622(5) 0.0413(15) Uani 1 1 d . . . H17 H 0.1693 0.9356 0.5097 0.050 Uiso 1 1 calc R . . C18 C 0.1028(6) 1.0378(8) 0.5845(8) 0.065(2) Uani 1 1 d . . . H18A H 0.1428 1.0904 0.5983 0.097 Uiso 1 1 calc R . . H18B H 0.0710 1.0297 0.6356 0.097 Uiso 1 1 calc R . . H18C H 0.0724 1.0640 0.5339 0.097 Uiso 1 1 calc R . . C19 C 0.1858(6) 0.8861(8) 0.6388(6) 0.057(2) Uani 1 1 d . . . H19A H 0.2058 0.8138 0.6249 0.086 Uiso 1 1 calc R . . H19B H 0.1557 0.8812 0.6915 0.086 Uiso 1 1 calc R . . H19C H 0.2274 0.9371 0.6498 0.086 Uiso 1 1 calc R . . C20 C 0.4235(5) 0.8636(8) 0.5526(5) 0.053(2) Uani 1 1 d . . . C21 C 0.4821(6) 0.8111(8) 0.5963(6) 0.060(2) Uani 1 1 d . . . C22 C 0.4948(7) 0.8354(10) 0.6870(7) 0.067(3) Uani 1 1 d . . . H22 H 0.5338 0.7988 0.7192 0.081 Uiso 1 1 calc R . . C23 C 0.4518(7) 0.9103(10) 0.7290(7) 0.073(3) Uani 1 1 d . . . C24 C 0.3980(7) 0.9673(10) 0.6824(7) 0.072(3) Uani 1 1 d . . . H24 H 0.3703 1.0218 0.7118 0.086 Uiso 1 1 calc R . . C25 C 0.3819(6) 0.9483(8) 0.5916(6) 0.057(2) Uani 1 1 d . . . C26 C 0.5326(6) 0.7290(10) 0.5492(7) 0.067(2) Uani 1 1 d . . . H26A H 0.5013 0.6745 0.5182 0.101 Uiso 1 1 calc R . . H26B H 0.5656 0.6923 0.5928 0.101 Uiso 1 1 calc R . . H26C H 0.5630 0.7679 0.5067 0.101 Uiso 1 1 calc R . . C27 C 0.4616(10) 0.9389(13) 0.8275(7) 0.101(5) Uani 1 1 d . . . H27A H 0.4561 0.8726 0.8629 0.152 Uiso 1 1 calc R . . H27B H 0.4234 0.9923 0.8435 0.152 Uiso 1 1 calc R . . H27C H 0.5116 0.9701 0.8389 0.152 Uiso 1 1 calc R . . C28 C 0.3277(6) 1.0142(8) 0.5373(7) 0.063(2) Uani 1 1 d . . . H28A H 0.3549 1.0698 0.5046 0.095 Uiso 1 1 calc R . . H28B H 0.2922 1.0500 0.5759 0.095 Uiso 1 1 calc R . . H28C H 0.3004 0.9663 0.4958 0.095 Uiso 1 1 calc R . . C29 C 0.2848(16) 1.120(2) 0.1869(15) 0.207(16) Uani 1 1 d D . . H29A H 0.3023 1.0571 0.1522 0.248 Uiso 1 1 calc R . . H29B H 0.2318 1.1335 0.1689 0.248 Uiso 1 1 calc R . . C30 C 0.2576(15) 1.1204(14) 0.9138(14) 0.180(14) Uani 1 1 d D . . H30A H 0.2361 1.0697 0.9571 0.216 Uiso 1 1 calc R . . H30B H 0.3126 1.1101 0.9180 0.216 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 0.0436(4) 0.0378(4) 0.0277(4) 0.00073(18) 0.0014(2) 0.00001(19) Cl1 0.0295(7) 0.0863(13) 0.0146(7) 0.0201(7) -0.0087(6) -0.0105(7) Cl2 0.0334(7) 0.0652(11) 0.0249(7) 0.0246(7) -0.0041(6) -0.0183(7) Cl5 0.260(9) 0.133(4) 0.147(5) 0.018(4) -0.051(6) -0.050(5) Cl6 0.465(18) 0.121(4) 0.128(5) 0.043(4) -0.044(7) 0.014(7) Cl7 0.195(7) 0.195(6) 0.113(4) -0.044(4) 0.046(4) -0.064(5) Cl8 0.166(7) 0.186(8) 0.56(2) -0.225(13) -0.069(10) 0.017(6) N1 0.046(3) 0.040(3) 0.028(3) 0.003(2) 0.002(3) 0.005(2) N2 0.047(3) 0.048(3) 0.026(3) 0.002(2) 0.004(3) 0.000(2) N3 0.048(4) 0.058(4) 0.033(3) 0.000(3) 0.007(3) -0.009(3) N4 0.054(4) 0.066(4) 0.031(3) -0.003(3) 0.006(3) -0.009(3) C1 0.051(4) 0.038(3) 0.027(3) 0.002(3) 0.004(3) -0.004(3) C2 0.052(4) 0.050(4) 0.030(3) 0.007(3) 0.007(3) 0.007(3) C3 0.054(4) 0.050(4) 0.031(3) 0.006(3) 0.001(3) -0.002(3) C4 0.050(4) 0.052(4) 0.032(3) -0.003(3) 0.005(3) -0.003(3) C5 0.043(4) 0.047(4) 0.032(3) -0.002(3) 0.002(3) -0.004(3) C6 0.058(5) 0.076(6) 0.040(4) 0.002(4) 0.005(4) -0.022(4) C7 0.060(5) 0.077(6) 0.039(4) 0.001(4) 0.007(4) -0.014(4) C8 0.044(4) 0.043(4) 0.031(3) 0.007(3) 0.002(3) 0.004(3) C9 0.052(4) 0.040(4) 0.034(4) 0.005(3) 0.003(3) 0.004(3) C10 0.055(4) 0.048(4) 0.037(4) 0.004(3) 0.006(4) -0.002(3) C11 0.055(4) 0.056(5) 0.034(4) 0.006(3) 0.010(3) 0.003(4) C12 0.059(5) 0.044(4) 0.035(4) 0.000(3) 0.002(3) 0.003(3) C13 0.049(4) 0.036(3) 0.030(3) 0.002(3) 0.002(3) 0.007(3) C14 0.051(4) 0.051(4) 0.031(3) 0.002(3) 0.006(3) -0.009(3) C15 0.070(6) 0.058(5) 0.044(4) -0.013(4) 0.003(4) 0.004(4) C16 0.052(4) 0.076(6) 0.037(4) -0.006(4) -0.004(4) 0.000(4) C17 0.045(4) 0.046(4) 0.033(3) -0.002(3) 0.004(3) 0.003(3) C18 0.071(6) 0.049(5) 0.074(6) -0.001(4) -0.002(5) 0.008(4) C19 0.066(5) 0.061(5) 0.045(5) 0.000(4) 0.001(4) 0.004(4) C20 0.060(5) 0.069(5) 0.031(4) -0.006(3) 0.003(4) -0.018(4) C21 0.065(6) 0.074(6) 0.040(5) -0.002(4) -0.004(4) -0.016(4) C22 0.076(6) 0.081(7) 0.044(5) 0.003(5) -0.009(5) -0.024(5) C23 0.090(8) 0.086(7) 0.041(5) -0.001(5) -0.005(5) -0.044(6) C24 0.091(8) 0.082(7) 0.043(5) -0.009(4) 0.013(5) -0.035(6) C25 0.063(5) 0.064(5) 0.044(4) -0.001(4) 0.012(4) -0.018(4) C26 0.063(6) 0.084(7) 0.054(6) -0.005(5) 0.000(5) 0.000(5) C27 0.132(12) 0.127(11) 0.044(6) 0.006(6) -0.010(7) -0.069(10) C28 0.073(6) 0.060(5) 0.056(5) 0.000(4) -0.001(5) -0.009(4) C29 0.13(2) 0.29(4) 0.20(4) -0.07(3) 0.02(2) -0.01(3) C30 0.19(3) 0.086(12) 0.27(4) -0.004(16) 0.11(3) -0.016(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 6.0952 (0.0653) x + 10.4736 (0.0253) y + 5.7321 (0.0536) z = 11.4652 (0.0062) * 0.0025 (0.0042) C1 * -0.0001 (0.0045) N1 * -0.0041 (0.0044) N2 * -0.0024 (0.0047) C2 * 0.0040 (0.0047) C3 Rms deviation of fitted atoms = 0.0030 - 3.4664 (0.0280) x + 7.9615 (0.0152) y + 11.2368 (0.0163) z = 9.8676 (0.0107) Angle to previous plane (with approximate esd) = 39.12 ( 0.27 ) * 0.1016 (0.0023) Pd1 * -0.0487 (0.0033) C1 * -0.0075 (0.0033) C5 * -0.0388 (0.0026) Cl1 * -0.0066 (0.0027) Cl2 -1.6768 (0.0100) C4 Rms deviation of fitted atoms = 0.0535 - 10.0849 (0.0731) x + 10.0361 (0.0347) y + 1.6858 (0.0747) z = 5.1234 (0.0624) Angle to previous plane (with approximate esd) = 44.67 ( 0.33 ) * -0.0037 (0.0050) C5 * 0.0133 (0.0054) N3 * -0.0076 (0.0058) N4 * 0.0159 (0.0065) C6 * -0.0178 (0.0062) C7 Rms deviation of fitted atoms = 0.0128 - 3.6071 (0.0662) x + 8.7411 (0.0308) y + 10.2680 (0.0395) z = 10.0119 (0.0255) Angle to previous plane (with approximate esd) = 40.37 ( 0.40 ) * 0.0000 (0.0000) Pd1 * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C5 -0.3261 (0.0092) Cl1 -0.2426 (0.0093) Cl2 Rms deviation of fitted atoms = 0.0000 ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C5 2.000(8) . ? Pd1 C1 2.005(7) . ? Pd1 Cl2 2.4255(15) . ? Pd1 Cl1 2.5076(16) . ? Cl5 C29 1.640(17) . ? Cl6 C29 1.613(18) . ? Cl7 C30 1.656(18) . ? Cl8 C30 1.630(15) . ? N1 C1 1.349(10) . ? N1 C2 1.398(9) . ? N1 C8 1.434(10) . ? N2 C1 1.361(9) . ? N2 C3 1.382(10) . ? N2 C4 1.460(10) . ? N3 C5 1.362(10) . ? N3 C7 1.406(11) . ? N3 C4 1.448(10) . ? N4 C5 1.356(10) . ? N4 C6 1.383(11) . ? N4 C20 1.447(10) . ? C2 C3 1.354(12) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.325(13) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.403(10) . ? C8 C9 1.417(11) . ? C9 C10 1.372(12) . ? C9 C14 1.528(11) . ? C10 C11 1.393(12) . ? C10 H10 0.9500 . ? C11 C12 1.356(12) . ? C11 H11 0.9500 . ? C12 C13 1.429(12) . ? C12 H12 0.9500 . ? C13 C17 1.537(11) . ? C14 C15 1.489(13) . ? C14 C16 1.530(12) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.511(12) . ? C17 C18 1.537(12) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.380(15) . ? C20 C25 1.416(14) . ? C21 C22 1.419(13) . ? C21 C26 1.542(16) . ? C22 C23 1.366(19) . ? C22 H22 0.9500 . ? C23 C24 1.367(19) . ? C23 C27 1.540(15) . ? C24 C25 1.418(13) . ? C24 H24 0.9500 . ? C25 C28 1.488(15) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Pd1 C1 87.2(3) . . ? C5 Pd1 Cl2 174.2(2) . . ? C1 Pd1 Cl2 93.4(2) . . ? C5 Pd1 Cl1 91.9(2) . . ? C1 Pd1 Cl1 172.4(2) . . ? Cl2 Pd1 Cl1 86.85(6) . . ? C1 N1 C2 110.4(6) . . ? C1 N1 C8 128.3(6) . . ? C2 N1 C8 120.8(6) . . ? C1 N2 C3 111.6(6) . . ? C1 N2 C4 122.5(6) . . ? C3 N2 C4 125.9(6) . . ? C5 N3 C7 111.8(7) . . ? C5 N3 C4 122.5(6) . . ? C7 N3 C4 125.7(7) . . ? C5 N4 C6 110.1(7) . . ? C5 N4 C20 125.3(7) . . ? C6 N4 C20 123.5(7) . . ? N1 C1 N2 104.9(6) . . ? N1 C1 Pd1 134.8(5) . . ? N2 C1 Pd1 120.1(6) . . ? C3 C2 N1 107.2(7) . . ? C3 C2 H2 126.4 . . ? N1 C2 H2 126.4 . . ? C2 C3 N2 106.0(6) . . ? C2 C3 H3 127.0 . . ? N2 C3 H3 127.0 . . ? N3 C4 N2 107.9(6) . . ? N3 C4 H4A 110.1 . . ? N2 C4 H4A 110.1 . . ? N3 C4 H4B 110.1 . . ? N2 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N4 C5 N3 104.0(6) . . ? N4 C5 Pd1 135.4(6) . . ? N3 C5 Pd1 120.6(5) . . ? C7 C6 N4 109.5(8) . . ? C7 C6 H6 125.3 . . ? N4 C6 H6 125.3 . . ? C6 C7 N3 104.5(8) . . ? C6 C7 H7 127.7 . . ? N3 C7 H7 127.7 . . ? C13 C8 C9 121.0(7) . . ? C13 C8 N1 120.3(7) . . ? C9 C8 N1 118.7(7) . . ? C10 C9 C8 118.3(7) . . ? C10 C9 C14 119.3(7) . . ? C8 C9 C14 122.4(7) . . ? C9 C10 C11 121.8(8) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 120.2(8) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.8(7) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C8 C13 C12 117.8(7) . . ? C8 C13 C17 122.6(7) . . ? C12 C13 C17 119.6(6) . . ? C15 C14 C9 112.5(6) . . ? C15 C14 C16 110.7(7) . . ? C9 C14 C16 110.0(7) . . ? C15 C14 H14 107.8 . . ? C9 C14 H14 107.8 . . ? C16 C14 H14 107.8 . . ? 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 . . ? 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 . . ? C19 C17 C18 110.2(7) . . ? C19 C17 C13 109.8(7) . . ? C18 C17 C13 110.3(7) . . ? C19 C17 H17 108.8 . . ? C18 C17 H17 108.8 . . ? C13 C17 H17 108.8 . . ? 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 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 122.6(8) . . ? C21 C20 N4 120.2(9) . . ? C25 C20 N4 116.8(8) . . ? C20 C21 C22 117.6(10) . . ? C20 C21 C26 121.7(8) . . ? C22 C21 C26 120.6(10) . . ? C23 C22 C21 121.2(11) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 119.8(9) . . ? C22 C23 C27 123.9(13) . . ? C24 C23 C27 116.3(13) . . ? C23 C24 C25 122.4(12) . . ? C23 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? C20 C25 C24 115.8(10) . . ? C20 C25 C28 120.4(8) . . ? C24 C25 C28 123.8(10) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Cl6 C29 Cl5 116.4(17) . . ? Cl6 C29 H29A 108.2 . . ? Cl5 C29 H29A 108.2 . . ? Cl6 C29 H29B 108.2 . . ? Cl5 C29 H29B 108.2 . . ? H29A C29 H29B 107.3 . . ? Cl8 C30 Cl7 123.7(18) . . ? Cl8 C30 H30A 106.4 . . ? Cl7 C30 H30A 106.4 . . ? Cl8 C30 H30B 106.4 . . ? Cl7 C30 H30B 106.4 . . ? H30A C30 H30B 106.5 . . ? 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 C2 N1 C1 N2 -0.3(8) . . . . ? C8 N1 C1 N2 171.8(7) . . . . ? C2 N1 C1 Pd1 173.0(6) . . . . ? C8 N1 C1 Pd1 -14.9(12) . . . . ? C3 N2 C1 N1 0.7(8) . . . . ? C4 N2 C1 N1 -176.3(6) . . . . ? C3 N2 C1 Pd1 -173.9(5) . . . . ? C4 N2 C1 Pd1 9.1(9) . . . . ? C5 Pd1 C1 N1 -138.8(8) . . . . ? Cl2 Pd1 C1 N1 46.9(7) . . . . ? Cl1 Pd1 C1 N1 138.3(13) . . . . ? C5 Pd1 C1 N2 33.7(6) . . . . ? Cl2 Pd1 C1 N2 -140.5(5) . . . . ? Cl1 Pd1 C1 N2 -49.2(19) . . . . ? C1 N1 C2 C3 -0.1(9) . . . . ? C8 N1 C2 C3 -172.9(7) . . . . ? N1 C2 C3 N2 0.5(9) . . . . ? C1 N2 C3 C2 -0.7(9) . . . . ? C4 N2 C3 C2 176.1(7) . . . . ? C5 N3 C4 N2 51.2(10) . . . . ? C7 N3 C4 N2 -127.8(9) . . . . ? C1 N2 C4 N3 -58.5(9) . . . . ? C3 N2 C4 N3 125.0(8) . . . . ? C6 N4 C5 N3 0.4(10) . . . . ? C20 N4 C5 N3 168.9(8) . . . . ? C6 N4 C5 Pd1 179.9(7) . . . . ? C20 N4 C5 Pd1 -11.7(14) . . . . ? C7 N3 C5 N4 1.7(10) . . . . ? C4 N3 C5 N4 -177.4(7) . . . . ? C7 N3 C5 Pd1 -177.9(6) . . . . ? C4 N3 C5 Pd1 3.0(10) . . . . ? C1 Pd1 C5 N4 140.7(9) . . . . ? Cl2 Pd1 C5 N4 -124.0(19) . . . . ? Cl1 Pd1 C5 N4 -46.8(9) . . . . ? C1 Pd1 C5 N3 -40.0(6) . . . . ? Cl2 Pd1 C5 N3 55(3) . . . . ? Cl1 Pd1 C5 N3 132.5(6) . . . . ? C5 N4 C6 C7 -2.5(12) . . . . ? C20 N4 C6 C7 -171.2(9) . . . . ? N4 C6 C7 N3 3.3(12) . . . . ? C5 N3 C7 C6 -3.2(11) . . . . ? C4 N3 C7 C6 175.9(9) . . . . ? C1 N1 C8 C13 78.3(10) . . . . ? C2 N1 C8 C13 -110.4(8) . . . . ? C1 N1 C8 C9 -104.2(9) . . . . ? C2 N1 C8 C9 67.2(9) . . . . ? C13 C8 C9 C10 -3.5(11) . . . . ? N1 C8 C9 C10 179.0(7) . . . . ? C13 C8 C9 C14 179.2(7) . . . . ? N1 C8 C9 C14 1.7(10) . . . . ? C8 C9 C10 C11 2.7(12) . . . . ? C14 C9 C10 C11 -180.0(7) . . . . ? C9 C10 C11 C12 -0.5(13) . . . . ? C10 C11 C12 C13 -0.9(12) . . . . ? C9 C8 C13 C12 2.2(10) . . . . ? N1 C8 C13 C12 179.6(6) . . . . ? C9 C8 C13 C17 -177.2(7) . . . . ? N1 C8 C13 C17 0.3(10) . . . . ? C11 C12 C13 C8 0.1(11) . . . . ? C11 C12 C13 C17 179.5(7) . . . . ? C10 C9 C14 C15 -67.8(10) . . . . ? C8 C9 C14 C15 109.4(9) . . . . ? C10 C9 C14 C16 56.0(10) . . . . ? C8 C9 C14 C16 -126.7(8) . . . . ? C8 C13 C17 C19 -116.0(8) . . . . ? C12 C13 C17 C19 64.7(9) . . . . ? C8 C13 C17 C18 122.4(8) . . . . ? C12 C13 C17 C18 -56.9(9) . . . . ? C5 N4 C20 C21 110.0(10) . . . . ? C6 N4 C20 C21 -83.1(12) . . . . ? C5 N4 C20 C25 -77.1(11) . . . . ? C6 N4 C20 C25 89.9(11) . . . . ? C25 C20 C21 C22 7.4(14) . . . . ? N4 C20 C21 C22 179.9(8) . . . . ? C25 C20 C21 C26 -172.5(9) . . . . ? N4 C20 C21 C26 0.0(14) . . . . ? C20 C21 C22 C23 -1.8(15) . . . . ? C26 C21 C22 C23 178.1(10) . . . . ? C21 C22 C23 C24 -3.4(15) . . . . ? C21 C22 C23 C27 178.9(10) . . . . ? C22 C23 C24 C25 3.2(15) . . . . ? C27 C23 C24 C25 -178.9(9) . . . . ? C21 C20 C25 C24 -7.5(13) . . . . ? N4 C20 C25 C24 179.8(8) . . . . ? C21 C20 C25 C28 170.1(9) . . . . ? N4 C20 C25 C28 -2.7(12) . . . . ? C23 C24 C25 C20 2.0(14) . . . . ? C23 C24 C25 C28 -175.4(10) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 3.369 _refine_diff_density_min -1.397 _refine_diff_density_rms 0.211 data_d:\as31mt03\p-1 _database_code_depnum_ccdc_archive 'CCDC 913066' #TrackingRef 'web_deposit_cif_file_5_michaelgardiner_1354099828.compound 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 F12 N6 P2 Pd' _chemical_formula_weight 758.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.960(3) _cell_length_b 11.4690(17) _cell_length_c 13.2140(16) _cell_angle_alpha 78.309(6) _cell_angle_beta 82.023(11) _cell_angle_gamma 63.410(11) _cell_volume 1452.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19000 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 27.15 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.850 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22436 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.15 _reflns_number_total 5876 _reflns_number_gt 5344 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0794P)^2^+3.3586P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.070(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5876 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.005 _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 0.60690(3) 0.69762(3) 0.75162(2) 0.03188(15) Uani 1 1 d . . . P1 P 0.80270(12) 0.28181(15) 0.65492(10) 0.0475(3) Uani 1 1 d . . . P2 P 0.24042(13) 0.52536(14) 0.80346(11) 0.0496(3) Uani 1 1 d . . . F1 F 0.9173(3) 0.1712(4) 0.5969(3) 0.0822(12) Uani 1 1 d . . . F2 F 0.8665(5) 0.2135(5) 0.7614(3) 0.0971(15) Uani 1 1 d . . . F3 F 0.6863(4) 0.3981(3) 0.7091(3) 0.0644(9) Uani 1 1 d . . . F4 F 0.7366(4) 0.3572(4) 0.5444(3) 0.0718(9) Uani 1 1 d . . . F5 F 0.7090(4) 0.2087(4) 0.6691(3) 0.0728(10) Uani 1 1 d . . . F6 F 0.8851(4) 0.3740(5) 0.6329(4) 0.0901(13) Uani 1 1 d . . . F7 F 0.3801(4) 0.4169(5) 0.7594(4) 0.0942(14) Uani 1 1 d . . . F8 F 0.2311(5) 0.6226(5) 0.6991(4) 0.1041(16) Uani 1 1 d . . . F9 F 0.1004(4) 0.6306(4) 0.8469(3) 0.0777(11) Uani 1 1 d . . . F10 F 0.2534(5) 0.4244(4) 0.9068(3) 0.0896(13) Uani 1 1 d . . . F11 F 0.1575(3) 0.4667(3) 0.7554(2) 0.0552(7) Uani 1 1 d . . . F12 F 0.3235(4) 0.5815(4) 0.8533(5) 0.0992(16) Uani 1 1 d . . . N1 N 0.8101(4) 0.6847(4) 0.5684(3) 0.0427(8) Uani 1 1 d . . . N2 N 0.6334(4) 0.6676(4) 0.5340(3) 0.0423(8) Uani 1 1 d . . . N3 N 0.4064(4) 0.7840(4) 0.5952(3) 0.0422(8) Uani 1 1 d . . . N4 N 0.3286(3) 0.9222(4) 0.7024(3) 0.0383(8) Uani 1 1 d . . . N5 N 0.7868(3) 0.5634(4) 0.8182(3) 0.0372(7) Uani 1 1 d . . . N6 N 0.5113(4) 0.7000(4) 0.8963(3) 0.0397(8) Uani 1 1 d . . . C1 C 0.6910(4) 0.6860(4) 0.6099(3) 0.0393(9) Uani 1 1 d . . . C2 C 0.8269(5) 0.6625(5) 0.4666(4) 0.0525(12) Uani 1 1 d . . . H2 H 0.9031 0.6564 0.4201 0.063 Uiso 1 1 calc R . . C3 C 0.7175(5) 0.6513(5) 0.4456(4) 0.0535(13) Uani 1 1 d . . . H3 H 0.7010 0.6353 0.3822 0.064 Uiso 1 1 calc R . . C4 C 0.4982(5) 0.6693(5) 0.5483(4) 0.0477(11) Uani 1 1 d . . . H4A H 0.4655 0.6741 0.4807 0.057 Uiso 1 1 calc R . . H4B H 0.5022 0.5877 0.5936 0.057 Uiso 1 1 calc R . . C5 C 0.4352(4) 0.8112(4) 0.6810(3) 0.0369(9) Uani 1 1 d . . . C6 C 0.2304(4) 0.9653(5) 0.6294(4) 0.0463(11) Uani 1 1 d . . . H6 H 0.1450 1.0411 0.6277 0.056 Uiso 1 1 calc R . . C7 C 0.2796(5) 0.8790(5) 0.5623(4) 0.0505(12) Uani 1 1 d . . . H7 H 0.2362 0.8823 0.5037 0.061 Uiso 1 1 calc R . . C8 C 0.9072(5) 0.7061(6) 0.6185(4) 0.0523(12) Uani 1 1 d . . . H8A H 0.8685 0.7305 0.6867 0.079 Uiso 1 1 calc R . . H8B H 0.9260 0.7774 0.5758 0.079 Uiso 1 1 calc R . . H8C H 0.9924 0.6248 0.6266 0.079 Uiso 1 1 calc R . . C9 C 0.3118(4) 0.9836(4) 0.7922(4) 0.0382(9) Uani 1 1 d . . . C10 C 0.2188(4) 0.9717(4) 0.8725(4) 0.0444(10) Uani 1 1 d . . . C11 C 0.2104(4) 1.0243(5) 0.9607(4) 0.0482(11) Uani 1 1 d . . . H11 H 0.1499 1.0150 1.0173 0.058 Uiso 1 1 calc R . . C12 C 0.2877(4) 1.0896(5) 0.9685(4) 0.0467(11) Uani 1 1 d . . . C13 C 0.3771(4) 1.1015(4) 0.8857(4) 0.0423(10) Uani 1 1 d . . . H13 H 0.4297 1.1470 0.8904 0.051 Uiso 1 1 calc R . . C14 C 0.3917(4) 1.0491(4) 0.7971(4) 0.0381(9) Uani 1 1 d . . . C15 C 0.1323(5) 0.9021(5) 0.8655(5) 0.0582(14) Uani 1 1 d . . . H15A H 0.0909 0.8849 0.9342 0.087 Uiso 1 1 calc R . . H15B H 0.1897 0.8183 0.8404 0.087 Uiso 1 1 calc R . . H15C H 0.0601 0.9579 0.8175 0.087 Uiso 1 1 calc R . . C16 C 0.2742(6) 1.1479(6) 1.0649(4) 0.0607(14) Uani 1 1 d . . . H16A H 0.2353 1.2443 1.0477 0.091 Uiso 1 1 calc R . . H16B H 0.3645 1.1143 1.0923 0.091 Uiso 1 1 calc R . . H16C H 0.2140 1.1226 1.1173 0.091 Uiso 1 1 calc R . . C17 C 0.4924(5) 1.0605(5) 0.7097(4) 0.0438(10) Uani 1 1 d . . . H17A H 0.5154 1.1320 0.7158 0.066 Uiso 1 1 calc R . . H17B H 0.4515 1.0798 0.6433 0.066 Uiso 1 1 calc R . . H17C H 0.5755 0.9772 0.7131 0.066 Uiso 1 1 calc R . . C18 C 0.8725(4) 0.4734(4) 0.8564(3) 0.0383(9) Uani 1 1 d . . . C19 C 0.9817(5) 0.3535(5) 0.9054(4) 0.0555(13) Uani 1 1 d . . . H19A H 0.9503 0.3277 0.9757 0.083 Uiso 1 1 calc R . . H19B H 1.0615 0.3698 0.9083 0.083 Uiso 1 1 calc R . . H19C H 1.0066 0.2824 0.8650 0.083 Uiso 1 1 calc R . . C20 C 0.4579(4) 0.6897(5) 0.9746(4) 0.0421(10) Uani 1 1 d . . . C21 C 0.3881(5) 0.6766(6) 1.0751(4) 0.0543(13) Uani 1 1 d . . . H21A H 0.3191 0.7638 1.0884 0.081 Uiso 1 1 calc R . . H21B H 0.4545 0.6382 1.1290 0.081 Uiso 1 1 calc R . . H21C H 0.3437 0.6189 1.0758 0.081 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 0.02356(18) 0.0319(2) 0.0339(2) -0.00231(12) -0.00446(10) -0.00695(12) P1 0.0325(5) 0.0706(8) 0.0424(6) -0.0166(6) 0.0001(4) -0.0224(5) P2 0.0434(6) 0.0495(7) 0.0582(8) -0.0060(6) -0.0160(5) -0.0194(5) F1 0.0442(17) 0.102(3) 0.062(2) -0.025(2) -0.0030(15) 0.0071(18) F2 0.088(3) 0.102(3) 0.063(2) -0.013(2) -0.039(2) 0.002(2) F3 0.082(2) 0.0609(19) 0.0522(17) -0.0167(15) 0.0169(15) -0.0356(17) F4 0.084(2) 0.069(2) 0.0529(18) -0.0071(17) -0.0070(17) -0.0255(19) F5 0.072(2) 0.077(2) 0.087(3) -0.026(2) 0.0124(18) -0.048(2) F6 0.065(2) 0.111(3) 0.111(3) -0.027(3) 0.013(2) -0.054(2) F7 0.0483(19) 0.114(3) 0.127(4) -0.063(3) -0.011(2) -0.021(2) F8 0.106(3) 0.121(4) 0.097(3) 0.034(3) -0.016(3) -0.078(3) F9 0.0513(18) 0.082(2) 0.098(3) -0.042(2) -0.0119(18) -0.0138(17) F10 0.128(4) 0.079(3) 0.064(2) 0.013(2) -0.048(2) -0.044(3) F11 0.0505(16) 0.077(2) 0.0481(15) -0.0169(15) -0.0050(12) -0.0331(15) F12 0.070(2) 0.066(2) 0.176(5) -0.038(3) -0.058(3) -0.0191(19) N1 0.0332(17) 0.0422(19) 0.0400(19) -0.0005(16) -0.0009(14) -0.0080(15) N2 0.0369(18) 0.0416(19) 0.0387(18) -0.0074(16) -0.0086(14) -0.0062(15) N3 0.0316(17) 0.0411(19) 0.051(2) -0.0099(17) -0.0143(15) -0.0085(15) N4 0.0249(15) 0.0360(17) 0.050(2) -0.0054(16) -0.0097(14) -0.0076(13) N5 0.0314(16) 0.0389(18) 0.0356(17) -0.0021(15) -0.0051(13) -0.0109(14) N6 0.0307(16) 0.0398(18) 0.043(2) -0.0032(16) -0.0030(14) -0.0112(14) C1 0.0331(19) 0.037(2) 0.039(2) -0.0022(17) -0.0051(16) -0.0078(16) C2 0.048(3) 0.050(3) 0.037(2) 0.000(2) 0.0027(19) -0.005(2) C3 0.050(3) 0.053(3) 0.037(2) -0.008(2) -0.0047(19) -0.003(2) C4 0.037(2) 0.045(2) 0.055(3) -0.013(2) -0.0134(19) -0.0072(18) C5 0.0292(18) 0.0337(19) 0.043(2) -0.0030(17) -0.0059(15) -0.0098(15) C6 0.031(2) 0.041(2) 0.062(3) -0.011(2) -0.0146(19) -0.0065(17) C7 0.038(2) 0.044(2) 0.064(3) -0.007(2) -0.021(2) -0.0085(19) C8 0.031(2) 0.065(3) 0.051(3) 0.005(2) -0.0015(18) -0.018(2) C9 0.0269(18) 0.0290(18) 0.050(2) -0.0061(17) -0.0086(16) -0.0031(14) C10 0.0286(19) 0.034(2) 0.061(3) -0.008(2) -0.0004(18) -0.0060(16) C11 0.0292(19) 0.041(2) 0.056(3) -0.006(2) 0.0013(18) -0.0015(17) C12 0.031(2) 0.040(2) 0.052(3) -0.010(2) -0.0091(18) 0.0022(17) C13 0.035(2) 0.036(2) 0.050(2) -0.0043(19) -0.0131(17) -0.0078(16) C14 0.0272(18) 0.0295(18) 0.048(2) 0.0006(17) -0.0112(16) -0.0044(14) C15 0.035(2) 0.051(3) 0.086(4) -0.015(3) 0.007(2) -0.018(2) C16 0.046(3) 0.062(3) 0.056(3) -0.019(3) -0.013(2) -0.001(2) C17 0.037(2) 0.041(2) 0.050(2) 0.0021(19) -0.0085(18) -0.0172(18) C18 0.0316(19) 0.045(2) 0.035(2) -0.0029(18) -0.0038(15) -0.0145(18) C19 0.038(2) 0.055(3) 0.059(3) 0.016(2) -0.014(2) -0.013(2) C20 0.033(2) 0.045(2) 0.043(2) -0.0025(19) -0.0060(17) -0.0134(17) C21 0.038(2) 0.068(3) 0.044(2) -0.001(2) 0.0031(19) -0.016(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 0.5230 (0.0258) x + 9.4968 (0.0155) y - 2.1074 (0.0315) z = 4.8759 (0.0371) * -0.0077 (0.0026) C1 * 0.0047 (0.0027) N1 * 0.0077 (0.0028) N2 * 0.0001 (0.0030) C2 * -0.0048 (0.0031) C3 Rms deviation of fitted atoms = 0.0057 6.5531 (0.0135) x + 11.2655 (0.0046) y + 3.5577 (0.0194) z = 14.4377 (0.0153) Angle to previous plane (with approximate esd) = 44.65 ( 0.15 ) * 0.0725 (0.0016) Pd1 * -0.0116 (0.0022) C1 * -0.0248 (0.0021) C5 * -0.0240 (0.0020) N5 * -0.0122 (0.0020) N6 -1.6824 (0.0070) C4 Rms deviation of fitted atoms = 0.0367 7.4787 (0.0199) x + 8.2170 (0.0194) y - 5.1385 (0.0298) z = 6.4230 (0.0364) Angle to previous plane (with approximate esd) = 42.27 ( 0.17 ) * -0.0020 (0.0026) C5 * 0.0002 (0.0029) N3 * 0.0030 (0.0028) N4 * -0.0028 (0.0030) C6 * 0.0016 (0.0031) C7 Rms deviation of fitted atoms = 0.0022 ; 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 1.971(4) . ? Pd1 C5 1.977(4) . ? Pd1 N6 2.048(4) . ? Pd1 N5 2.061(3) . ? P1 F2 1.555(4) . ? P1 F5 1.564(3) . ? P1 F1 1.573(4) . ? P1 F3 1.590(4) . ? P1 F4 1.621(4) . ? P1 F6 1.636(4) . ? P2 F8 1.571(4) . ? P2 F10 1.578(4) . ? P2 F9 1.587(4) . ? P2 F12 1.594(4) . ? P2 F11 1.601(3) . ? P2 F7 1.604(4) . ? N1 C1 1.339(6) . ? N1 C2 1.391(6) . ? N1 C8 1.459(7) . ? N2 C1 1.353(6) . ? N2 C3 1.372(6) . ? N2 C4 1.459(6) . ? N3 C5 1.346(6) . ? N3 C7 1.388(6) . ? N3 C4 1.450(6) . ? N4 C5 1.337(5) . ? N4 C6 1.397(6) . ? N4 C9 1.449(6) . ? N5 C18 1.120(5) . ? N6 C20 1.128(6) . ? C2 C3 1.332(8) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.342(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.397(6) . ? C9 C14 1.399(6) . ? C10 C11 1.391(8) . ? C10 C15 1.509(7) . ? C11 C12 1.383(7) . ? C11 H11 0.9500 . ? C12 C13 1.391(7) . ? C12 C16 1.516(7) . ? C13 C14 1.380(7) . ? C13 H13 0.9500 . ? C14 C17 1.511(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.457(6) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.453(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C5 84.25(18) . . ? C1 Pd1 N6 174.92(17) . . ? C5 Pd1 N6 93.90(16) . . ? C1 Pd1 N5 93.09(15) . . ? C5 Pd1 N5 173.98(16) . . ? N6 Pd1 N5 88.30(14) . . ? F2 P1 F5 93.6(3) . . ? F2 P1 F1 92.6(2) . . ? F5 P1 F1 90.8(2) . . ? F2 P1 F3 89.5(2) . . ? F5 P1 F3 90.3(2) . . ? F1 P1 F3 177.5(2) . . ? F2 P1 F4 178.1(3) . . ? F5 P1 F4 88.0(2) . . ? F1 P1 F4 88.3(2) . . ? F3 P1 F4 89.5(2) . . ? F2 P1 F6 92.2(3) . . ? F5 P1 F6 172.9(3) . . ? F1 P1 F6 93.1(3) . . ? F3 P1 F6 85.6(2) . . ? F4 P1 F6 86.2(2) . . ? F8 P2 F10 178.3(3) . . ? F8 P2 F9 90.7(3) . . ? F10 P2 F9 90.9(3) . . ? F8 P2 F12 91.7(3) . . ? F10 P2 F12 88.6(3) . . ? F9 P2 F12 90.6(2) . . ? F8 P2 F11 89.5(2) . . ? F10 P2 F11 90.2(2) . . ? F9 P2 F11 89.55(19) . . ? F12 P2 F11 178.8(2) . . ? F8 P2 F7 89.7(3) . . ? F10 P2 F7 88.6(3) . . ? F9 P2 F7 178.6(2) . . ? F12 P2 F7 90.7(2) . . ? F11 P2 F7 89.1(2) . . ? C1 N1 C2 109.0(4) . . ? C1 N1 C8 126.8(4) . . ? C2 N1 C8 124.2(4) . . ? C1 N2 C3 110.8(4) . . ? C1 N2 C4 122.2(4) . . ? C3 N2 C4 127.0(4) . . ? C5 N3 C7 110.3(4) . . ? C5 N3 C4 122.6(4) . . ? C7 N3 C4 127.2(4) . . ? C5 N4 C6 109.9(4) . . ? C5 N4 C9 125.4(3) . . ? C6 N4 C9 124.6(4) . . ? C18 N5 Pd1 165.8(4) . . ? C20 N6 Pd1 172.8(4) . . ? N1 C1 N2 105.9(4) . . ? N1 C1 Pd1 131.8(3) . . ? N2 C1 Pd1 122.2(3) . . ? C3 C2 N1 108.1(4) . . ? C3 C2 H2 125.9 . . ? N1 C2 H2 125.9 . . ? C2 C3 N2 106.2(5) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? N3 C4 N2 107.9(4) . . ? N3 C4 H4A 110.1 . . ? N2 C4 H4A 110.1 . . ? N3 C4 H4B 110.1 . . ? N2 C4 H4B 110.1 . . ? H4A C4 H4B 108.4 . . ? N4 C5 N3 106.3(4) . . ? N4 C5 Pd1 131.4(3) . . ? N3 C5 Pd1 122.3(3) . . ? C7 C6 N4 107.0(4) . . ? C7 C6 H6 126.5 . . ? N4 C6 H6 126.5 . . ? C6 C7 N3 106.6(4) . . ? C6 C7 H7 126.7 . . ? N3 C7 H7 126.7 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 122.2(4) . . ? C10 C9 N4 118.4(4) . . ? C14 C9 N4 119.3(4) . . ? C11 C10 C9 117.5(4) . . ? C11 C10 C15 120.8(5) . . ? C9 C10 C15 121.6(5) . . ? C12 C11 C10 121.8(5) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 118.7(5) . . ? C11 C12 C16 120.5(5) . . ? C13 C12 C16 120.8(5) . . ? C14 C13 C12 122.1(5) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C9 117.6(4) . . ? C13 C14 C17 120.8(4) . . ? C9 C14 C17 121.5(4) . . ? 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 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 C19 178.0(5) . . ? 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 . . ? N6 C20 C21 179.5(5) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C1 Pd1 N5 C18 -101.6(15) . . . . ? C5 Pd1 N5 C18 -38(2) . . . . ? N6 Pd1 N5 C18 73.5(15) . . . . ? C1 Pd1 N6 C20 24(4) . . . . ? C5 Pd1 N6 C20 92(3) . . . . ? N5 Pd1 N6 C20 -82(3) . . . . ? C2 N1 C1 N2 -1.2(5) . . . . ? C8 N1 C1 N2 177.2(4) . . . . ? C2 N1 C1 Pd1 174.4(3) . . . . ? C8 N1 C1 Pd1 -7.1(7) . . . . ? C3 N2 C1 N1 1.5(5) . . . . ? C4 N2 C1 N1 -177.1(4) . . . . ? C3 N2 C1 Pd1 -174.6(3) . . . . ? C4 N2 C1 Pd1 6.8(6) . . . . ? C5 Pd1 C1 N1 141.5(4) . . . . ? N6 Pd1 C1 N1 -149.8(15) . . . . ? N5 Pd1 C1 N1 -44.0(4) . . . . ? C5 Pd1 C1 N2 -43.5(4) . . . . ? N6 Pd1 C1 N2 25.3(19) . . . . ? N5 Pd1 C1 N2 131.1(4) . . . . ? C1 N1 C2 C3 0.5(6) . . . . ? C8 N1 C2 C3 -178.0(5) . . . . ? N1 C2 C3 N2 0.5(6) . . . . ? C1 N2 C3 C2 -1.3(6) . . . . ? C4 N2 C3 C2 177.3(4) . . . . ? C5 N3 C4 N2 -51.3(6) . . . . ? C7 N3 C4 N2 129.6(5) . . . . ? C1 N2 C4 N3 47.2(6) . . . . ? C3 N2 C4 N3 -131.1(5) . . . . ? C6 N4 C5 N3 0.5(5) . . . . ? C9 N4 C5 N3 176.0(4) . . . . ? C6 N4 C5 Pd1 -179.4(3) . . . . ? C9 N4 C5 Pd1 -3.9(7) . . . . ? C7 N3 C5 N4 -0.2(5) . . . . ? C4 N3 C5 N4 -179.5(4) . . . . ? C7 N3 C5 Pd1 179.7(3) . . . . ? C4 N3 C5 Pd1 0.4(6) . . . . ? C1 Pd1 C5 N4 -140.0(4) . . . . ? N6 Pd1 C5 N4 44.7(4) . . . . ? N5 Pd1 C5 N4 156.0(13) . . . . ? C1 Pd1 C5 N3 40.1(4) . . . . ? N6 Pd1 C5 N3 -135.2(4) . . . . ? N5 Pd1 C5 N3 -23.9(17) . . . . ? C5 N4 C6 C7 -0.6(6) . . . . ? C9 N4 C6 C7 -176.2(4) . . . . ? N4 C6 C7 N3 0.4(6) . . . . ? C5 N3 C7 C6 -0.1(6) . . . . ? C4 N3 C7 C6 179.1(5) . . . . ? C5 N4 C9 C10 -105.0(5) . . . . ? C6 N4 C9 C10 69.9(6) . . . . ? C5 N4 C9 C14 73.0(5) . . . . ? C6 N4 C9 C14 -112.1(5) . . . . ? C14 C9 C10 C11 -1.9(6) . . . . ? N4 C9 C10 C11 176.1(4) . . . . ? C14 C9 C10 C15 179.3(4) . . . . ? N4 C9 C10 C15 -2.7(6) . . . . ? C9 C10 C11 C12 1.9(6) . . . . ? C15 C10 C11 C12 -179.4(4) . . . . ? C10 C11 C12 C13 -0.7(7) . . . . ? C10 C11 C12 C16 178.9(4) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? C16 C12 C13 C14 179.8(4) . . . . ? C12 C13 C14 C9 0.6(6) . . . . ? C12 C13 C14 C17 -178.4(4) . . . . ? C10 C9 C14 C13 0.7(6) . . . . ? N4 C9 C14 C13 -177.3(3) . . . . ? C10 C9 C14 C17 179.7(4) . . . . ? N4 C9 C14 C17 1.8(6) . . . . ? Pd1 N5 C18 C19 11(16) . . . . ? Pd1 N6 C20 C21 -65(67) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 1.642 _refine_diff_density_min -1.199 _refine_diff_density_rms 0.105 data_d:\as28ch27 _database_code_depnum_ccdc_archive 'CCDC 913067' #TrackingRef 'web_deposit_cif_file_6_michaelgardiner_1354099828.compound S1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cl N2' _chemical_formula_weight 264.79 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5500(18) _cell_length_b 16.6320(13) _cell_length_c 10.9560(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.33(3) _cell_angle_gamma 90.00 _cell_volume 1541.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 23956 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 28.83 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71090 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24625 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 28.83 _reflns_number_total 3788 _reflns_number_gt 3685 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0448P)^2^+0.9059P] 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 3788 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Cl1 Cl 0.41195(4) 0.091500(19) 0.79260(3) 0.02760(12) Uani 1 1 d . . . N1 N 0.80427(13) 0.14378(7) 1.18808(10) 0.0232(2) Uani 1 1 d . . . N2 N 0.64136(14) 0.13335(7) 1.01916(11) 0.0269(3) Uani 1 1 d . . . C1 C 0.70677(16) 0.09375(8) 1.11883(13) 0.0255(3) Uani 1 1 d . . . H1 H 0.6875 0.0392 1.1376 0.031 Uiso 1 1 calc R . . C2 C 0.79929(17) 0.21825(8) 1.13093(14) 0.0279(3) Uani 1 1 d . . . H2 H 0.8560 0.2651 1.1604 0.033 Uiso 1 1 calc R . . C3 C 0.69753(18) 0.21087(9) 1.02476(14) 0.0296(3) Uani 1 1 d . . . H3 H 0.6700 0.2518 0.9650 0.036 Uiso 1 1 calc R . . H1N H 0.566(3) 0.1125(15) 0.953(2) 0.055 Uiso 1 1 d . . . C4 C 0.89964(16) 0.12421(8) 1.30491(12) 0.0249(3) Uani 1 1 d . . . C5 C 1.04791(17) 0.08904(9) 1.30300(13) 0.0281(3) Uani 1 1 d . . . C6 C 1.13856(19) 0.07350(10) 1.41725(15) 0.0337(3) Uani 1 1 d . . . H6 H 1.2395 0.0492 1.4201 0.040 Uiso 1 1 calc R . . C7 C 1.0836(2) 0.09303(10) 1.52677(15) 0.0375(4) Uani 1 1 d . . . H7 H 1.1478 0.0830 1.6036 0.045 Uiso 1 1 calc R . . C8 C 0.9364(2) 0.12679(10) 1.52406(14) 0.0358(3) Uani 1 1 d . . . H8 H 0.9003 0.1397 1.5997 0.043 Uiso 1 1 calc R . . C9 C 0.83861(18) 0.14263(9) 1.41345(13) 0.0293(3) Uani 1 1 d . . . C10 C 1.10618(18) 0.06474(10) 1.18371(14) 0.0330(3) Uani 1 1 d . . . H10 H 1.0447 0.0961 1.1150 0.040 Uiso 1 1 calc R . . C11 C 1.0731(2) -0.02510(11) 1.15831(16) 0.0421(4) Uani 1 1 d . . . H11A H 1.1106 -0.0404 1.0812 0.063 Uiso 1 1 calc R . . H11B H 0.9592 -0.0351 1.1512 0.063 Uiso 1 1 calc R . . H11C H 1.1284 -0.0571 1.2264 0.063 Uiso 1 1 calc R . . C12 C 1.2811(2) 0.08226(14) 1.1833(2) 0.0501(5) Uani 1 1 d . . . H12A H 1.3114 0.0655 1.1043 0.075 Uiso 1 1 calc R . . H12B H 1.3440 0.0525 1.2505 0.075 Uiso 1 1 calc R . . H12C H 1.3003 0.1400 1.1950 0.075 Uiso 1 1 calc R . . C13 C 0.6732(2) 0.17582(10) 1.41264(15) 0.0363(3) Uani 1 1 d . . . H13 H 0.6225 0.1809 1.3248 0.044 Uiso 1 1 calc R . . C14 C 0.5737(2) 0.11813(13) 1.4777(2) 0.0470(4) Uani 1 1 d . . . H14A H 0.4673 0.1403 1.4761 0.070 Uiso 1 1 calc R . . H14B H 0.6231 0.1109 1.5635 0.070 Uiso 1 1 calc R . . H14C H 0.5670 0.0661 1.4354 0.070 Uiso 1 1 calc R . . C15 C 0.6767(3) 0.25935(13) 1.4717(3) 0.0684(8) Uani 1 1 d . . . H15A H 0.5683 0.2791 1.4695 0.103 Uiso 1 1 calc R . . H15B H 0.7358 0.2964 1.4259 0.103 Uiso 1 1 calc R . . H15C H 0.7281 0.2561 1.5575 0.103 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 Cl1 0.03039(19) 0.02208(17) 0.02693(18) 0.00336(11) -0.00739(12) -0.00128(11) N1 0.0228(5) 0.0232(5) 0.0240(5) -0.0012(4) 0.0046(4) 0.0008(4) N2 0.0249(5) 0.0267(6) 0.0284(6) -0.0020(4) 0.0017(4) 0.0017(4) C1 0.0252(6) 0.0243(6) 0.0272(6) -0.0017(5) 0.0044(5) 0.0005(5) C2 0.0302(7) 0.0222(6) 0.0311(7) 0.0006(5) 0.0040(5) -0.0002(5) C3 0.0316(7) 0.0252(6) 0.0319(7) 0.0027(5) 0.0037(5) 0.0032(5) C4 0.0269(6) 0.0246(6) 0.0229(6) 0.0001(5) 0.0030(5) -0.0040(5) C5 0.0268(6) 0.0300(7) 0.0273(7) 0.0053(5) 0.0030(5) -0.0028(5) C6 0.0301(7) 0.0338(7) 0.0348(8) 0.0093(6) -0.0030(6) -0.0060(6) C7 0.0464(9) 0.0359(8) 0.0267(7) 0.0072(6) -0.0069(6) -0.0157(7) C8 0.0507(9) 0.0337(8) 0.0230(6) -0.0010(5) 0.0053(6) -0.0126(7) C9 0.0368(7) 0.0258(6) 0.0266(7) -0.0016(5) 0.0089(5) -0.0060(5) C10 0.0295(7) 0.0401(8) 0.0308(7) 0.0101(6) 0.0090(6) 0.0085(6) C11 0.0532(10) 0.0418(9) 0.0331(8) 0.0020(7) 0.0128(7) 0.0135(8) C12 0.0307(8) 0.0664(13) 0.0560(11) 0.0219(9) 0.0162(8) 0.0125(8) C13 0.0417(8) 0.0349(8) 0.0358(8) -0.0033(6) 0.0177(6) 0.0002(6) C14 0.0400(9) 0.0486(10) 0.0542(11) 0.0024(8) 0.0130(8) -0.0115(8) C15 0.0662(14) 0.0397(10) 0.110(2) -0.0230(12) 0.0501(15) -0.0089(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 N1 C1 1.3341(18) . ? N1 C2 1.3857(18) . ? N1 C4 1.4515(17) . ? N2 C1 1.3275(19) . ? N2 C3 1.3741(19) . ? C2 C3 1.353(2) . ? C4 C5 1.399(2) . ? C4 C9 1.4000(19) . ? C5 C6 1.398(2) . ? C5 C10 1.519(2) . ? C6 C7 1.389(3) . ? C7 C8 1.374(3) . ? C8 C9 1.394(2) . ? C9 C13 1.517(2) . ? C10 C12 1.524(2) . ? C10 C11 1.539(3) . ? C13 C14 1.525(2) . ? C13 C15 1.531(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 N1 C2 108.96(12) . . ? C1 N1 C4 125.91(12) . . ? C2 N1 C4 125.13(12) . . ? C1 N2 C3 109.02(12) . . ? N2 C1 N1 108.20(12) . . ? C3 C2 N1 106.33(12) . . ? C2 C3 N2 107.49(13) . . ? C5 C4 C9 123.66(13) . . ? C5 C4 N1 118.36(12) . . ? C9 C4 N1 117.97(12) . . ? C6 C5 C4 116.74(14) . . ? C6 C5 C10 120.86(14) . . ? C4 C5 C10 122.34(13) . . ? C7 C6 C5 121.16(15) . . ? C8 C7 C6 120.01(15) . . ? C7 C8 C9 121.87(15) . . ? C8 C9 C4 116.51(14) . . ? C8 C9 C13 121.01(14) . . ? C4 C9 C13 122.46(14) . . ? C5 C10 C12 113.31(15) . . ? C5 C10 C11 109.83(13) . . ? C12 C10 C11 109.87(15) . . ? C9 C13 C14 110.53(15) . . ? C9 C13 C15 111.50(16) . . ? C14 C13 C15 110.57(15) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 28.83 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.435 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.047 data_d:\as31ch45 _database_code_depnum_ccdc_archive 'CCDC 913068' #TrackingRef 'web_deposit_cif_file_7_michaelgardiner_1354099828.compound S2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H38 Cl4 F12 N6 P2 Pd' _chemical_formula_weight 1032.81 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' P P 0.1023 0.0942 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0310(13) _cell_length_b 13.2510(9) _cell_length_c 17.8350(15) _cell_angle_alpha 92.644(5) _cell_angle_beta 104.078(12) _cell_angle_gamma 93.119(11) _cell_volume 2063.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 27085 _cell_measurement_theta_min 1.18 _cell_measurement_theta_max 27.13 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.873 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Low data completion ratio is due to the limitations of the instrument available at the Australian Synchrotron operating under rotation data collection with a fixed detector and affects some high angle data. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71080 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31998 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 27.13 _reflns_number_total 8365 _reflns_number_gt 7669 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0633P)^2^+9.0502P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8365 _refine_ls_number_parameters 513 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.51253(3) 0.72929(2) 0.730471(18) 0.01997(11) Uani 1 1 d . . . Cl1 Cl 0.85501(17) 0.50576(12) 0.66772(10) 0.0514(4) Uani 1 1 d . . . Cl2 Cl 1.1018(2) 0.37893(17) 0.65756(12) 0.0684(5) Uani 1 1 d . . . Cl3 Cl 1.25244(19) 1.04315(12) 0.90902(10) 0.0546(4) Uani 1 1 d . . . Cl4 Cl 1.4270(2) 0.86565(13) 0.90479(13) 0.0665(5) Uani 1 1 d . . . P1 P 0.66833(12) 0.75249(8) 0.50960(7) 0.0254(2) Uani 1 1 d . . . P2 P 0.77035(13) 1.17650(9) 0.86911(7) 0.0282(3) Uani 1 1 d . . . F1 F 0.5034(3) 0.6952(3) 0.4996(3) 0.0561(10) Uani 1 1 d . . . F2 F 0.7032(5) 0.7453(3) 0.60087(19) 0.0546(9) Uani 1 1 d . . . F3 F 0.8323(3) 0.8074(2) 0.51725(19) 0.0387(7) Uani 1 1 d . . . F4 F 0.6322(4) 0.7566(2) 0.41722(17) 0.0430(7) Uani 1 1 d . . . F5 F 0.7389(3) 0.6442(2) 0.5033(2) 0.0407(7) Uani 1 1 d . . . F6 F 0.5980(3) 0.8592(2) 0.51574(18) 0.0399(7) Uani 1 1 d . . . F7 F 0.7402(4) 1.0682(2) 0.8223(2) 0.0488(9) Uani 1 1 d . . . F8 F 0.7504(4) 1.1232(3) 0.9448(2) 0.0501(8) Uani 1 1 d . . . F9 F 0.7995(4) 1.2845(2) 0.9161(2) 0.0468(8) Uani 1 1 d . . . F10 F 0.7897(4) 1.2290(3) 0.7930(2) 0.0468(8) Uani 1 1 d . . . F11 F 0.5909(3) 1.1927(2) 0.8444(2) 0.0473(8) Uani 1 1 d . . . F12 F 0.9491(3) 1.1607(2) 0.89332(19) 0.0402(7) Uani 1 1 d . . . N1 N 0.2048(4) 0.7262(3) 0.6123(2) 0.0207(7) Uani 1 1 d . . . N2 N 0.3280(4) 0.5955(3) 0.6017(2) 0.0223(7) Uani 1 1 d . . . N3 N 0.4960(4) 0.5087(3) 0.6963(2) 0.0233(7) Uani 1 1 d . . . N4 N 0.5697(4) 0.5377(3) 0.8193(2) 0.0229(7) Uani 1 1 d . . . N5 N 0.5093(4) 0.8771(3) 0.6994(2) 0.0282(8) Uani 1 1 d . . . N6 N 0.7003(4) 0.7786(3) 0.8183(2) 0.0249(7) Uani 1 1 d . . . C1 C 0.3354(5) 0.6831(3) 0.6436(2) 0.0231(8) Uani 1 1 d . . . C2 C 0.1166(5) 0.6646(3) 0.5499(3) 0.0256(9) Uani 1 1 d . . . H2 H 0.0201 0.6783 0.5179 0.031 Uiso 1 1 calc R . . C3 C 0.1943(5) 0.5827(3) 0.5438(3) 0.0266(9) Uani 1 1 d . . . H3 H 0.1636 0.5267 0.5070 0.032 Uiso 1 1 calc R . . C4 C 0.4524(5) 0.5279(3) 0.6142(3) 0.0260(9) Uani 1 1 d . . . H4A H 0.5410 0.5594 0.5983 0.031 Uiso 1 1 calc R . . H4B H 0.4188 0.4634 0.5829 0.031 Uiso 1 1 calc R . . C5 C 0.5261(4) 0.5842(3) 0.7524(3) 0.0235(8) Uani 1 1 d . . . C6 C 0.5671(5) 0.4336(3) 0.8040(3) 0.0280(9) Uani 1 1 d . . . H6 H 0.5927 0.3843 0.8412 0.034 Uiso 1 1 calc R . . C7 C 0.5214(5) 0.4161(3) 0.7266(3) 0.0265(9) Uani 1 1 d . . . H7 H 0.5092 0.3523 0.6985 0.032 Uiso 1 1 calc R . . C8 C 0.1590(5) 0.8238(3) 0.6351(2) 0.0231(8) Uani 1 1 d . . . C9 C 0.1717(5) 0.9041(3) 0.5881(3) 0.0264(9) Uani 1 1 d . . . C10 C 0.1284(5) 0.9978(4) 0.6100(3) 0.0316(10) Uani 1 1 d . . . H10 H 0.1370 1.0539 0.5796 0.038 Uiso 1 1 calc R . . C11 C 0.0723(6) 1.0112(4) 0.6762(3) 0.0355(11) Uani 1 1 d . . . C12 C 0.0572(6) 0.9288(4) 0.7191(3) 0.0365(11) Uani 1 1 d . . . H12 H 0.0169 0.9374 0.7634 0.044 Uiso 1 1 calc R . . C13 C 0.0994(5) 0.8334(4) 0.6995(3) 0.0299(10) Uani 1 1 d . . . C14 C 0.2276(6) 0.8908(4) 0.5159(3) 0.0326(10) Uani 1 1 d . . . H14A H 0.2419 0.9571 0.4955 0.049 Uiso 1 1 calc R . . H14B H 0.1522 0.8478 0.4770 0.049 Uiso 1 1 calc R . . H14C H 0.3253 0.8588 0.5279 0.049 Uiso 1 1 calc R . . C15 C 0.0305(8) 1.1149(4) 0.7004(4) 0.0528(16) Uani 1 1 d . . . H15A H 0.1200 1.1631 0.7085 0.079 Uiso 1 1 calc R . . H15B H -0.0026 1.1112 0.7487 0.079 Uiso 1 1 calc R . . H15C H -0.0528 1.1374 0.6597 0.079 Uiso 1 1 calc R . . C16 C 0.0700(7) 0.7449(4) 0.7452(3) 0.0411(12) Uani 1 1 d . . . H16A H -0.0397 0.7246 0.7318 0.062 Uiso 1 1 calc R . . H16B H 0.1038 0.7644 0.8007 0.062 Uiso 1 1 calc R . . H16C H 0.1267 0.6880 0.7330 0.062 Uiso 1 1 calc R . . C17 C 0.6136(5) 0.5834(3) 0.8976(2) 0.0242(8) Uani 1 1 d . . . C18 C 0.5008(5) 0.6133(3) 0.9330(3) 0.0253(9) Uani 1 1 d . . . C19 C 0.5476(5) 0.6543(3) 1.0090(3) 0.0284(9) Uani 1 1 d . . . H19 H 0.4728 0.6770 1.0340 0.034 Uiso 1 1 calc R . . C20 C 0.7014(5) 0.6630(4) 1.0495(3) 0.0298(9) Uani 1 1 d . . . C21 C 0.8096(5) 0.6321(4) 1.0115(3) 0.0295(10) Uani 1 1 d . . . H21 H 0.9146 0.6381 1.0384 0.035 Uiso 1 1 calc R . . C22 C 0.7692(5) 0.5927(3) 0.9351(3) 0.0262(9) Uani 1 1 d . . . C23 C 0.3328(5) 0.6008(4) 0.8929(3) 0.0309(10) Uani 1 1 d . . . H23A H 0.3177 0.6209 0.8395 0.046 Uiso 1 1 calc R . . H23B H 0.2757 0.6437 0.9205 0.046 Uiso 1 1 calc R . . H23C H 0.2960 0.5298 0.8926 0.046 Uiso 1 1 calc R . . C24 C 0.7486(6) 0.7003(4) 1.1331(3) 0.0405(12) Uani 1 1 d . . . H24A H 0.7403 0.6438 1.1658 0.061 Uiso 1 1 calc R . . H24B H 0.6817 0.7526 1.1427 0.061 Uiso 1 1 calc R . . H24C H 0.8547 0.7289 1.1455 0.061 Uiso 1 1 calc R . . C25 C 0.8904(5) 0.5601(4) 0.8953(3) 0.0331(10) Uani 1 1 d . . . H25A H 0.9920 0.5827 0.9277 0.050 Uiso 1 1 calc R . . H25B H 0.8752 0.5903 0.8451 0.050 Uiso 1 1 calc R . . H25C H 0.8827 0.4861 0.8873 0.050 Uiso 1 1 calc R . . C26 C 0.5296(6) 0.9539(4) 0.6795(3) 0.0352(11) Uani 1 1 d . . . C27 C 0.5531(8) 1.0539(4) 0.6508(4) 0.0570(19) Uani 1 1 d . . . H27A H 0.5337 1.0480 0.5942 0.086 Uiso 1 1 calc R . . H27B H 0.6588 1.0807 0.6731 0.086 Uiso 1 1 calc R . . H27C H 0.4826 1.0999 0.6659 0.086 Uiso 1 1 calc R . . C28 C 0.7915(5) 0.8216(3) 0.8656(3) 0.0285(9) Uani 1 1 d . . . C29 C 0.9096(6) 0.8751(4) 0.9262(3) 0.0392(12) Uani 1 1 d . . . H29A H 0.9139 0.8439 0.9754 0.059 Uiso 1 1 calc R . . H29B H 0.8863 0.9461 0.9311 0.059 Uiso 1 1 calc R . . H29C H 1.0086 0.8715 0.9132 0.059 Uiso 1 1 calc R . . C30 C 0.9208(9) 0.3846(7) 0.6791(6) 0.075(2) Uani 1 1 d . . . H30A H 0.8464 0.3350 0.6444 0.090 Uiso 1 1 calc R . . H30B H 0.9292 0.3663 0.7331 0.090 Uiso 1 1 calc R . . C31 C 1.4080(8) 0.9896(6) 0.8826(6) 0.069(2) Uani 1 1 d . . . H31A H 1.3953 0.9940 0.8262 0.083 Uiso 1 1 calc R . . H31B H 1.5033 1.0300 0.9092 0.083 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 0.01792(15) 0.01877(16) 0.02148(16) 0.00137(12) 0.00141(11) 0.00167(11) Cl1 0.0434(7) 0.0566(8) 0.0564(8) 0.0014(7) 0.0164(6) 0.0064(6) Cl2 0.0495(9) 0.0933(13) 0.0753(11) 0.0437(11) 0.0280(8) 0.0276(9) Cl3 0.0530(8) 0.0466(8) 0.0653(10) 0.0012(7) 0.0155(7) 0.0106(6) Cl4 0.0761(11) 0.0455(8) 0.0884(13) 0.0065(9) 0.0378(10) 0.0155(8) P1 0.0225(5) 0.0228(5) 0.0316(6) 0.0039(5) 0.0072(4) 0.0037(4) P2 0.0231(5) 0.0265(5) 0.0339(6) 0.0033(5) 0.0047(5) 0.0017(4) F1 0.0253(15) 0.0478(19) 0.097(3) 0.027(2) 0.0152(17) -0.0008(13) F2 0.071(2) 0.063(2) 0.0333(16) 0.0130(16) 0.0140(16) 0.0233(19) F3 0.0254(13) 0.0327(14) 0.0545(18) 0.0039(13) 0.0032(13) -0.0002(11) F4 0.0500(18) 0.0472(17) 0.0280(14) -0.0007(13) 0.0020(13) 0.0079(14) F5 0.0335(14) 0.0233(13) 0.0599(19) -0.0004(13) 0.0004(14) 0.0070(11) F6 0.0402(16) 0.0342(15) 0.0478(17) 0.0034(13) 0.0127(14) 0.0163(12) F7 0.060(2) 0.0297(15) 0.0463(18) -0.0033(13) -0.0066(16) 0.0082(14) F8 0.0462(18) 0.063(2) 0.0430(18) 0.0160(17) 0.0135(15) -0.0012(16) F9 0.0391(16) 0.0361(16) 0.060(2) -0.0114(15) 0.0041(15) 0.0019(13) F10 0.0498(18) 0.0462(18) 0.0477(18) 0.0206(15) 0.0144(15) 0.0063(15) F11 0.0240(14) 0.0453(17) 0.067(2) 0.0031(16) 0.0007(14) 0.0021(12) F12 0.0240(13) 0.0483(17) 0.0492(17) 0.0095(15) 0.0083(12) 0.0073(12) N1 0.0183(15) 0.0211(16) 0.0216(16) 0.0013(14) 0.0031(13) 0.0009(13) N2 0.0208(16) 0.0219(16) 0.0230(16) 0.0007(14) 0.0033(14) 0.0024(13) N3 0.0210(16) 0.0206(16) 0.0267(18) 0.0004(14) 0.0025(14) 0.0036(13) N4 0.0196(15) 0.0234(17) 0.0255(17) 0.0033(14) 0.0046(14) 0.0029(13) N5 0.0268(18) 0.0266(19) 0.0279(19) 0.0051(16) -0.0005(15) 0.0024(15) N6 0.0231(17) 0.0223(17) 0.0283(18) 0.0082(15) 0.0043(15) -0.0017(14) C1 0.0225(19) 0.0211(19) 0.025(2) 0.0023(16) 0.0044(16) 0.0029(15) C2 0.0230(19) 0.026(2) 0.026(2) -0.0003(17) 0.0022(16) 0.0003(16) C3 0.023(2) 0.027(2) 0.026(2) -0.0005(18) 0.0004(17) 0.0020(16) C4 0.0248(19) 0.026(2) 0.026(2) -0.0005(17) 0.0034(17) 0.0072(16) C5 0.0162(17) 0.027(2) 0.027(2) 0.0024(17) 0.0040(15) 0.0045(15) C6 0.027(2) 0.021(2) 0.035(2) 0.0054(18) 0.0058(18) 0.0027(16) C7 0.0231(19) 0.0213(19) 0.035(2) 0.0022(18) 0.0077(17) 0.0016(16) C8 0.0205(18) 0.0213(19) 0.025(2) -0.0011(16) 0.0015(16) 0.0024(15) C9 0.0216(19) 0.028(2) 0.027(2) -0.0008(18) 0.0009(16) 0.0043(16) C10 0.030(2) 0.026(2) 0.034(2) -0.0005(19) 0.0007(19) 0.0055(18) C11 0.038(2) 0.030(2) 0.034(2) -0.008(2) -0.001(2) 0.011(2) C12 0.042(3) 0.042(3) 0.026(2) -0.003(2) 0.008(2) 0.014(2) C13 0.029(2) 0.033(2) 0.026(2) -0.0001(19) 0.0032(18) 0.0084(18) C14 0.032(2) 0.034(2) 0.034(2) 0.007(2) 0.011(2) 0.0098(19) C15 0.071(4) 0.039(3) 0.044(3) -0.010(2) 0.003(3) 0.024(3) C16 0.049(3) 0.043(3) 0.039(3) 0.012(2) 0.019(2) 0.014(2) C17 0.0243(19) 0.0237(19) 0.024(2) 0.0055(17) 0.0043(16) 0.0032(16) C18 0.0226(19) 0.0235(19) 0.030(2) 0.0093(18) 0.0061(17) 0.0007(16) C19 0.028(2) 0.028(2) 0.031(2) 0.0068(19) 0.0107(18) 0.0013(17) C20 0.032(2) 0.028(2) 0.028(2) 0.0044(19) 0.0061(18) -0.0042(18) C21 0.022(2) 0.033(2) 0.032(2) 0.0082(19) 0.0020(17) -0.0029(17) C22 0.024(2) 0.026(2) 0.029(2) 0.0080(18) 0.0047(17) 0.0031(16) C23 0.022(2) 0.035(2) 0.037(2) 0.005(2) 0.0062(18) 0.0024(17) C24 0.040(3) 0.048(3) 0.031(2) -0.001(2) 0.007(2) -0.008(2) C25 0.024(2) 0.041(3) 0.036(2) 0.006(2) 0.0081(19) 0.0058(19) C26 0.039(3) 0.029(2) 0.031(2) 0.004(2) -0.004(2) 0.000(2) C27 0.073(4) 0.032(3) 0.050(3) 0.019(3) -0.016(3) -0.011(3) C28 0.030(2) 0.028(2) 0.026(2) 0.0070(19) 0.0039(19) 0.0006(18) C29 0.033(2) 0.043(3) 0.034(3) -0.001(2) -0.005(2) -0.005(2) C30 0.054(4) 0.075(5) 0.110(7) 0.042(5) 0.036(4) 0.023(4) C31 0.051(4) 0.059(4) 0.104(6) 0.013(4) 0.029(4) 0.013(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 5.4171 (0.0171) x - 6.2227 (0.0271) y + 13.8800 (0.0275) z = 2.8681 (0.0306) * 0.0031 (0.0027) N1 * 0.0004 (0.0027) N2 * -0.0022 (0.0026) C1 * -0.0029 (0.0028) C2 * 0.0015 (0.0028) C3 Rms deviation of fitted atoms = 0.0022 - 7.1233 (0.0083) x + 2.0826 (0.0191) y + 13.7288 (0.0174) z = 7.8466 (0.0192) Angle to previous plane (with approximate esd) = 37.68 ( 0.18 ) * 0.0497 (0.0017) Pd1 * 0.0227 (0.0022) C1 * -0.0476 (0.0022) C5 * -0.0461 (0.0021) N5 * 0.0212 (0.0021) N6 -1.5369 (0.0064) C4 Rms deviation of fitted atoms = 0.0396 8.9692 (0.0030) x + 0.5889 (0.0296) y - 5.4934 (0.0367) z = 0.9267 (0.0308) Angle to previous plane (with approximate esd) = 35.92 ( 0.14 ) * -0.0038 (0.0025) N3 * -0.0006 (0.0025) N4 * 0.0027 (0.0024) C5 * -0.0017 (0.0027) C6 * 0.0034 (0.0027) C7 Rms deviation of fitted atoms = 0.0027 ; 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 1.983(4) . ? Pd1 C5 1.984(4) . ? Pd1 N5 2.060(4) . ? Pd1 N6 2.062(4) . ? Cl1 C30 1.745(8) . ? Cl2 C30 1.773(8) . ? Cl3 C31 1.760(7) . ? Cl4 C31 1.715(8) . ? P1 F3 1.586(3) . ? P1 F2 1.589(3) . ? P1 F6 1.591(3) . ? P1 F1 1.601(3) . ? P1 F4 1.604(3) . ? P1 F5 1.612(3) . ? P2 F12 1.595(3) . ? P2 F10 1.595(4) . ? P2 F8 1.596(4) . ? P2 F9 1.601(3) . ? P2 F11 1.602(3) . ? P2 F7 1.602(3) . ? N1 C1 1.346(5) . ? N1 C2 1.398(5) . ? N1 C8 1.449(5) . ? N2 C1 1.341(5) . ? N2 C3 1.381(5) . ? N2 C4 1.455(5) . ? N3 C5 1.350(5) . ? N3 C7 1.371(6) . ? N3 C4 1.458(6) . ? N4 C5 1.350(6) . ? N4 C6 1.391(5) . ? N4 C17 1.449(5) . ? N5 C26 1.113(6) . ? N6 C28 1.131(6) . ? C2 C3 1.339(6) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 C7 1.347(7) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C13 1.386(6) . ? C8 C9 1.400(7) . ? C9 C10 1.390(6) . ? C9 C14 1.500(7) . ? C10 C11 1.402(7) . ? C10 H10 0.9500 . ? C11 C12 1.381(8) . ? C11 C15 1.516(6) . ? C12 C13 1.394(6) . ? C12 H12 0.9500 . ? C13 C16 1.507(8) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.389(6) . ? C17 C22 1.397(6) . ? C18 C19 1.393(6) . ? C18 C23 1.508(6) . ? C19 C20 1.397(6) . ? C19 H19 0.9500 . ? C20 C21 1.387(7) . ? C20 C24 1.499(7) . ? C21 C22 1.391(6) . ? C21 H21 0.9500 . ? C22 C25 1.513(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.466(7) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.448(6) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? 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 C5 85.87(17) . . ? C1 Pd1 N5 93.19(16) . . ? C5 Pd1 N5 174.45(17) . . ? C1 Pd1 N6 178.25(17) . . ? C5 Pd1 N6 94.81(15) . . ? N5 Pd1 N6 85.98(14) . . ? F3 P1 F2 90.8(2) . . ? F3 P1 F6 90.36(17) . . ? F2 P1 F6 91.06(18) . . ? F3 P1 F1 178.3(2) . . ? F2 P1 F1 90.5(2) . . ? F6 P1 F1 90.69(18) . . ? F3 P1 F4 90.03(19) . . ? F2 P1 F4 178.5(2) . . ? F6 P1 F4 90.19(17) . . ? F1 P1 F4 88.6(2) . . ? F3 P1 F5 89.87(16) . . ? F2 P1 F5 88.96(19) . . ? F6 P1 F5 179.77(19) . . ? F1 P1 F5 89.09(18) . . ? F4 P1 F5 89.79(18) . . ? F12 P2 F10 90.49(18) . . ? F12 P2 F8 89.63(18) . . ? F10 P2 F8 179.6(2) . . ? F12 P2 F9 90.29(18) . . ? F10 P2 F9 90.1(2) . . ? F8 P2 F9 90.3(2) . . ? F12 P2 F11 179.7(2) . . ? F10 P2 F11 89.21(19) . . ? F8 P2 F11 90.7(2) . . ? F9 P2 F11 89.70(18) . . ? F12 P2 F7 89.99(18) . . ? F10 P2 F7 90.17(19) . . ? F8 P2 F7 89.4(2) . . ? F9 P2 F7 179.6(2) . . ? F11 P2 F7 90.02(19) . . ? C1 N1 C2 110.2(3) . . ? C1 N1 C8 127.2(3) . . ? C2 N1 C8 122.6(3) . . ? C1 N2 C3 111.4(3) . . ? C1 N2 C4 122.7(3) . . ? C3 N2 C4 125.8(3) . . ? C5 N3 C7 111.5(4) . . ? C5 N3 C4 122.3(4) . . ? C7 N3 C4 126.1(4) . . ? C5 N4 C6 110.1(4) . . ? C5 N4 C17 128.1(4) . . ? C6 N4 C17 121.8(4) . . ? C26 N5 Pd1 168.4(4) . . ? C28 N6 Pd1 167.8(4) . . ? N2 C1 N1 105.2(3) . . ? N2 C1 Pd1 123.1(3) . . ? N1 C1 Pd1 131.7(3) . . ? C3 C2 N1 106.8(4) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 106.5(4) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N2 C4 N3 108.5(3) . . ? N2 C4 H4A 110.0 . . ? N3 C4 H4A 110.0 . . ? N2 C4 H4B 110.0 . . ? N3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? N4 C5 N3 105.0(4) . . ? N4 C5 Pd1 131.9(3) . . ? N3 C5 Pd1 123.1(3) . . ? C7 C6 N4 107.0(4) . . ? C7 C6 H6 126.5 . . ? N4 C6 H6 126.5 . . ? C6 C7 N3 106.4(4) . . ? C6 C7 H7 126.8 . . ? N3 C7 H7 126.8 . . ? C13 C8 C9 122.8(4) . . ? C13 C8 N1 119.5(4) . . ? C9 C8 N1 117.6(4) . . ? C10 C9 C8 117.6(4) . . ? C10 C9 C14 120.2(4) . . ? C8 C9 C14 122.1(4) . . ? C9 C10 C11 121.1(5) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 119.0(4) . . ? C12 C11 C15 120.8(5) . . ? C10 C11 C15 120.2(5) . . ? C11 C12 C13 121.9(5) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C8 C13 C12 117.5(5) . . ? C8 C13 C16 123.0(4) . . ? C12 C13 C16 119.4(5) . . ? 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 . . ? C11 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C11 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 122.8(4) . . ? C18 C17 N4 119.3(4) . . ? C22 C17 N4 117.9(4) . . ? C17 C18 C19 117.4(4) . . ? C17 C18 C23 122.5(4) . . ? C19 C18 C23 120.0(4) . . ? C18 C19 C20 121.9(4) . . ? C18 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? C21 C20 C19 118.3(4) . . ? C21 C20 C24 120.5(4) . . ? C19 C20 C24 121.2(5) . . ? C20 C21 C22 122.0(4) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C17 117.5(4) . . ? C21 C22 C25 120.6(4) . . ? C17 C22 C25 122.0(4) . . ? C18 C23 H23A 109.5 . . ? C18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N5 C26 C27 178.2(5) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N6 C28 C29 179.1(5) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? Cl1 C30 Cl2 111.0(5) . . ? Cl1 C30 H30A 109.4 . . ? Cl2 C30 H30A 109.4 . . ? Cl1 C30 H30B 109.4 . . ? Cl2 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? Cl4 C31 Cl3 113.7(5) . . ? Cl4 C31 H31A 108.8 . . ? Cl3 C31 H31A 108.8 . . ? Cl4 C31 H31B 108.8 . . ? Cl3 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? 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 C1 Pd1 N5 C26 -110.8(19) . . . . ? C5 Pd1 N5 C26 -31(3) . . . . ? N6 Pd1 N5 C26 67.7(19) . . . . ? C1 Pd1 N6 C28 90(5) . . . . ? C5 Pd1 N6 C28 -157.2(18) . . . . ? N5 Pd1 N6 C28 28.3(18) . . . . ? C3 N2 C1 N1 0.3(5) . . . . ? C4 N2 C1 N1 176.5(4) . . . . ? C3 N2 C1 Pd1 -178.6(3) . . . . ? C4 N2 C1 Pd1 -2.4(6) . . . . ? C2 N1 C1 N2 -0.5(5) . . . . ? C8 N1 C1 N2 -177.8(4) . . . . ? C2 N1 C1 Pd1 178.3(4) . . . . ? C8 N1 C1 Pd1 1.0(7) . . . . ? C5 Pd1 C1 N2 -35.5(4) . . . . ? N5 Pd1 C1 N2 139.0(4) . . . . ? N6 Pd1 C1 N2 77(5) . . . . ? C5 Pd1 C1 N1 145.9(5) . . . . ? N5 Pd1 C1 N1 -39.6(4) . . . . ? N6 Pd1 C1 N1 -101(5) . . . . ? C1 N1 C2 C3 0.6(5) . . . . ? C8 N1 C2 C3 178.0(4) . . . . ? N1 C2 C3 N2 -0.4(5) . . . . ? C1 N2 C3 C2 0.1(5) . . . . ? C4 N2 C3 C2 -176.0(4) . . . . ? C1 N2 C4 N3 51.5(5) . . . . ? C3 N2 C4 N3 -132.8(4) . . . . ? C5 N3 C4 N2 -50.4(5) . . . . ? C7 N3 C4 N2 134.1(4) . . . . ? C6 N4 C5 N3 0.3(5) . . . . ? C17 N4 C5 N3 -179.3(4) . . . . ? C6 N4 C5 Pd1 -176.8(3) . . . . ? C17 N4 C5 Pd1 3.5(7) . . . . ? C7 N3 C5 N4 -0.7(5) . . . . ? C4 N3 C5 N4 -176.7(4) . . . . ? C7 N3 C5 Pd1 176.8(3) . . . . ? C4 N3 C5 Pd1 0.8(5) . . . . ? C1 Pd1 C5 N4 -147.0(4) . . . . ? N5 Pd1 C5 N4 132.6(15) . . . . ? N6 Pd1 C5 N4 34.6(4) . . . . ? C1 Pd1 C5 N3 36.2(3) . . . . ? N5 Pd1 C5 N3 -44.2(17) . . . . ? N6 Pd1 C5 N3 -142.2(3) . . . . ? C5 N4 C6 C7 0.1(5) . . . . ? C17 N4 C6 C7 179.8(4) . . . . ? N4 C6 C7 N3 -0.5(5) . . . . ? C5 N3 C7 C6 0.7(5) . . . . ? C4 N3 C7 C6 176.6(4) . . . . ? C1 N1 C8 C13 -79.6(6) . . . . ? C2 N1 C8 C13 103.5(5) . . . . ? C1 N1 C8 C9 103.1(5) . . . . ? C2 N1 C8 C9 -73.9(5) . . . . ? C13 C8 C9 C10 3.0(6) . . . . ? N1 C8 C9 C10 -179.8(4) . . . . ? C13 C8 C9 C14 -176.2(4) . . . . ? N1 C8 C9 C14 1.1(6) . . . . ? C8 C9 C10 C11 -0.8(6) . . . . ? C14 C9 C10 C11 178.4(4) . . . . ? C9 C10 C11 C12 -1.3(7) . . . . ? C9 C10 C11 C15 178.0(5) . . . . ? C10 C11 C12 C13 1.4(8) . . . . ? C15 C11 C12 C13 -177.9(5) . . . . ? C9 C8 C13 C12 -2.9(7) . . . . ? N1 C8 C13 C12 179.9(4) . . . . ? C9 C8 C13 C16 173.3(4) . . . . ? N1 C8 C13 C16 -3.9(7) . . . . ? C11 C12 C13 C8 0.6(7) . . . . ? C11 C12 C13 C16 -175.7(5) . . . . ? C5 N4 C17 C18 77.9(6) . . . . ? C6 N4 C17 C18 -101.7(5) . . . . ? C5 N4 C17 C22 -103.9(5) . . . . ? C6 N4 C17 C22 76.5(6) . . . . ? C22 C17 C18 C19 0.2(7) . . . . ? N4 C17 C18 C19 178.3(4) . . . . ? C22 C17 C18 C23 -178.5(4) . . . . ? N4 C17 C18 C23 -0.5(7) . . . . ? C17 C18 C19 C20 -1.7(7) . . . . ? C23 C18 C19 C20 177.1(4) . . . . ? C18 C19 C20 C21 1.8(7) . . . . ? C18 C19 C20 C24 -175.5(5) . . . . ? C19 C20 C21 C22 -0.4(7) . . . . ? C24 C20 C21 C22 177.0(5) . . . . ? C20 C21 C22 C17 -1.0(7) . . . . ? C20 C21 C22 C25 179.8(5) . . . . ? C18 C17 C22 C21 1.1(7) . . . . ? N4 C17 C22 C21 -177.0(4) . . . . ? C18 C17 C22 C25 -179.7(4) . . . . ? N4 C17 C22 C25 2.2(7) . . . . ? Pd1 N5 C26 C27 96(21) . . . . ? Pd1 N6 C28 C29 -177(100) . . . . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 2.013 _refine_diff_density_min -1.564 _refine_diff_density_rms 0.131