# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; National Institute of Advanced Industrial Science and Technology, Tukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan ; _publ_contact_author_email libiao-han@aist.go.jp _publ_contact_author_fax +81-29-861- _publ_contact_author_phone +81-29-861-4855 #============================================================================== _publ_contact_author_name 'Li-Biao Han' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Highly Regioselective Addition and Dehydrogenative Cross-Coupling of H-Heteroatoms with Alkynes Using An Unconventional Palladacycle Catalyst ; loop_ _publ_author_name 'Qing Xu.' 'Ruwei Shen.' 'Yutaka Ono.' R.Nagahata 'Shigeru Shimada ' M.Goto ; Li-Biao Han ; data_General _database_code_depnum_ccdc_archive 'CCDC 773371' #TrackingRef '- 773371_Pd-hexamer_rev2.cif' _audit_creation_date 2010-11-10 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'DIRDIF99-PATTY (Gould, et al., 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C72 H54 O12 P6 Pd6' _chemical_formula_moiety 'C72 H54 O12 P6 Pd6' _chemical_formula_weight 1935.45 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,+Y,1/2+Z 3 +X,1/2-Y,1/2+Z 4 1/2-X,1/2-Y,+Z 5 -X,-Y,-Z 6 1/2+X,-Y,1/2-Z 7 -X,1/2+Y,1/2-Z 8 1/2+X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 20.7526(17) _cell_length_b 17.8092(14) _cell_length_c 18.6170(15) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 6880.6(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5330 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 28.15 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.080 _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3792.00 _exptl_absorpt_coefficient_mu 1.738 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8187 _exptl_absorpt_correction_T_max 0.8736 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 45474 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). For C8-C12, "similar U restraint" was applied. ; _reflns_number_total 8562 _reflns_number_gt 5818 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1505 _refine_ls_number_restraints 24 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 8562 _refine_ls_number_parameters 433 _refine_ls_goodness_of_fit_ref 1.258 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0250P)^2^+60.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 2.130 _refine_diff_density_min -1.120 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Pd Pd -0.999 1.007 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Pd(1) Pd 0.60713(3) -0.03025(3) 0.40392(3) 0.03004(14) Uani 1.0 1 d . . . Pd(2) Pd 0.55740(3) 0.08651(3) 0.60292(3) 0.03072(14) Uani 1.0 1 d . . . Pd(3) Pd 0.44005(3) 0.11861(3) 0.43017(3) 0.03219(15) Uani 1.0 1 d . . . P(1) P 0.67865(10) 0.00407(13) 0.54425(11) 0.0376(5) Uani 1.0 1 d . . . P(2) P 0.44913(10) 0.20123(11) 0.57179(10) 0.0314(5) Uani 1.0 1 d . . . P(3) P 0.51317(10) 0.04436(11) 0.30448(9) 0.0311(5) Uani 1.0 1 d . . . O(1) O 0.6324(3) -0.0526(3) 0.5094(3) 0.0336(12) Uani 1.0 1 d . . . O(2) O 0.6511(3) 0.0526(4) 0.6036(3) 0.0380(13) Uani 1.0 1 d . . . O(3) O 0.4630(3) 0.1205(3) 0.5995(3) 0.0314(11) Uani 1.0 1 d . . . O(4) O 0.4179(3) 0.2055(3) 0.4980(3) 0.0366(13) Uani 1.0 1 d . . . O(5) O 0.4661(3) 0.0288(3) 0.3670(3) 0.0340(12) Uani 1.0 1 d . . . O(6) O 0.5738(3) -0.0017(3) 0.3041(3) 0.0337(12) Uani 1.0 1 d . . . C(1) C 0.6743(4) 0.0461(5) 0.4037(5) 0.0362(18) Uani 1.0 1 d . . . C(2) C 0.6940(5) 0.0861(6) 0.3437(5) 0.046(2) Uani 1.0 1 d . . . C(3) C 0.7442(5) 0.1367(6) 0.3492(6) 0.059(3) Uani 1.0 1 d . . . C(4) C 0.7759(5) 0.1482(6) 0.4144(6) 0.056(3) Uani 1.0 1 d . . . C(5) C 0.7575(5) 0.1069(6) 0.4737(6) 0.055(3) Uani 1.0 1 d . . . C(6) C 0.7069(4) 0.0568(5) 0.4692(5) 0.040(2) Uani 1.0 1 d . . . C(7) C 0.7442(5) -0.0466(6) 0.5837(5) 0.048(3) Uani 1.0 1 d . . . C(8) C 0.7749(7) -0.1023(9) 0.5492(7) 0.108(5) Uani 1.0 1 d . . . C(9) C 0.8280(7) -0.1376(9) 0.5798(8) 0.104(4) Uani 1.0 1 d . . . C(10) C 0.8486(6) -0.1177(8) 0.6457(7) 0.076(3) Uani 1.0 1 d . . . C(11) C 0.8197(5) -0.0622(6) 0.6807(5) 0.055(3) Uani 1.0 1 d . . . C(12) C 0.7677(5) -0.0249(6) 0.6511(5) 0.046(2) Uani 1.0 1 d . . . C(13) C 0.5782(4) 0.1916(5) 0.5873(4) 0.0334(17) Uani 1.0 1 d . . . C(14) C 0.6409(5) 0.2198(6) 0.5956(5) 0.047(3) Uani 1.0 1 d . . . C(15) C 0.6509(5) 0.2959(6) 0.5933(5) 0.052(3) Uani 1.0 1 d . . . C(16) C 0.6007(5) 0.3456(6) 0.5797(5) 0.047(3) Uani 1.0 1 d . . . C(17) C 0.5394(5) 0.3188(5) 0.5714(4) 0.041(2) Uani 1.0 1 d . . . C(18) C 0.5278(4) 0.2420(5) 0.5760(4) 0.0361(18) Uani 1.0 1 d . . . C(19) C 0.3958(4) 0.2468(4) 0.6325(4) 0.0272(15) Uani 1.0 1 d . . . C(20) C 0.3416(6) 0.2827(7) 0.6083(5) 0.062(3) Uani 1.0 1 d . . . C(21) C 0.2989(6) 0.3181(8) 0.6556(7) 0.078(4) Uani 1.0 1 d . . . C(22) C 0.3130(5) 0.3189(7) 0.7271(6) 0.063(3) Uani 1.0 1 d . . . C(23) C 0.3664(5) 0.2840(6) 0.7522(5) 0.057(3) Uani 1.0 1 d . . . C(24) C 0.4077(5) 0.2493(6) 0.7054(5) 0.047(3) Uani 1.0 1 d . . . C(25) C 0.4989(5) 0.1793(5) 0.3716(4) 0.0383(19) Uani 1.0 1 d . . . C(26) C 0.5100(5) 0.2550(5) 0.3817(5) 0.045(2) Uani 1.0 1 d . . . C(27) C 0.5515(5) 0.2928(5) 0.3356(5) 0.047(3) Uani 1.0 1 d . . . C(28) C 0.5804(5) 0.2571(6) 0.2790(5) 0.047(3) Uani 1.0 1 d . . . C(29) C 0.5684(4) 0.1830(5) 0.2673(4) 0.041(2) Uani 1.0 1 d . . . C(30) C 0.5286(4) 0.1429(5) 0.3136(4) 0.0357(18) Uani 1.0 1 d . . . C(31) C 0.4743(4) 0.0217(5) 0.2210(4) 0.0330(17) Uani 1.0 1 d . . . C(32) C 0.5103(5) 0.0025(5) 0.1618(4) 0.041(2) Uani 1.0 1 d . . . C(33) C 0.4796(5) -0.0139(5) 0.0977(4) 0.047(3) Uani 1.0 1 d . . . C(34) C 0.4148(6) -0.0121(6) 0.0919(5) 0.057(3) Uani 1.0 1 d . . . C(35) C 0.3777(6) 0.0053(6) 0.1507(6) 0.062(3) Uani 1.0 1 d . . . C(36) C 0.4061(5) 0.0227(6) 0.2168(5) 0.049(3) Uani 1.0 1 d . . . H(1) H 0.6730 0.0787 0.2989 0.0553 Uiso 1.0 1 calc R . . H(2) H 0.7573 0.1641 0.3079 0.0702 Uiso 1.0 1 calc R . . H(3) H 0.8096 0.1840 0.4179 0.0673 Uiso 1.0 1 calc R . . H(4) H 0.7799 0.1130 0.5179 0.0665 Uiso 1.0 1 calc R . . H(5) H 0.7601 -0.1178 0.5032 0.1301 Uiso 1.0 1 calc R . . H(6) H 0.8499 -0.1759 0.5540 0.1243 Uiso 1.0 1 calc R . . H(7) H 0.8838 -0.1434 0.6671 0.0910 Uiso 1.0 1 calc R . . H(8) H 0.8351 -0.0479 0.7267 0.0658 Uiso 1.0 1 calc R . . H(9) H 0.7479 0.0153 0.6764 0.0548 Uiso 1.0 1 calc R . . H(10) H 0.6761 0.1865 0.6026 0.0566 Uiso 1.0 1 calc R . . H(11) H 0.6930 0.3150 0.6012 0.0626 Uiso 1.0 1 calc R . . H(12) H 0.6090 0.3979 0.5762 0.0569 Uiso 1.0 1 calc R . . H(13) H 0.5048 0.3525 0.5625 0.0492 Uiso 1.0 1 calc R . . H(14) H 0.3327 0.2835 0.5582 0.0747 Uiso 1.0 1 calc R . . H(15) H 0.2608 0.3412 0.6382 0.0939 Uiso 1.0 1 calc R . . H(16) H 0.2851 0.3441 0.7596 0.0759 Uiso 1.0 1 calc R . . H(17) H 0.3752 0.2835 0.8022 0.0680 Uiso 1.0 1 calc R . . H(18) H 0.4456 0.2263 0.7237 0.0565 Uiso 1.0 1 calc R . . H(19) H 0.4895 0.2810 0.4199 0.0540 Uiso 1.0 1 calc R . . H(20) H 0.5599 0.3446 0.3435 0.0570 Uiso 1.0 1 calc R . . H(21) H 0.6087 0.2839 0.2481 0.0567 Uiso 1.0 1 calc R . . H(22) H 0.5873 0.1585 0.2272 0.0487 Uiso 1.0 1 calc R . . H(23) H 0.5560 0.0004 0.1649 0.0488 Uiso 1.0 1 calc R . . H(24) H 0.5047 -0.0266 0.0569 0.0563 Uiso 1.0 1 calc R . . H(25) H 0.3948 -0.0228 0.0472 0.0685 Uiso 1.0 1 calc R . . H(26) H 0.3321 0.0055 0.1465 0.0747 Uiso 1.0 1 calc R . . H(27) H 0.3806 0.0347 0.2575 0.0586 Uiso 1.0 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Pd(1) 0.0360(3) 0.0353(3) 0.0189(3) 0.0039(3) -0.0043(3) -0.0047(3) Pd(2) 0.0370(3) 0.0357(3) 0.0195(3) 0.0072(3) -0.0022(3) -0.0051(3) Pd(3) 0.0445(4) 0.0349(3) 0.0171(3) 0.0089(3) -0.0044(3) -0.0052(3) P(1) 0.0367(12) 0.0519(14) 0.0244(9) 0.0108(10) -0.0062(8) -0.0119(9) P(2) 0.0427(12) 0.0326(10) 0.0189(8) 0.0073(9) -0.0022(8) -0.0058(8) P(3) 0.0428(12) 0.0331(11) 0.0173(8) 0.0045(9) -0.0048(8) -0.0043(8) O(1) 0.042(3) 0.042(4) 0.017(3) 0.006(3) -0.004(2) -0.001(2) O(2) 0.035(3) 0.051(4) 0.028(3) 0.012(3) -0.004(3) -0.015(3) O(3) 0.038(3) 0.032(3) 0.024(3) 0.002(3) -0.004(3) -0.005(3) O(4) 0.049(4) 0.036(3) 0.024(3) 0.010(3) -0.007(3) -0.009(3) O(5) 0.046(4) 0.031(3) 0.024(3) 0.009(3) -0.003(3) -0.004(3) O(6) 0.041(3) 0.043(3) 0.017(3) 0.009(3) -0.003(2) -0.004(3) C(1) 0.039(5) 0.036(5) 0.034(4) -0.000(4) -0.001(4) -0.006(4) C(2) 0.048(6) 0.048(6) 0.043(5) -0.008(5) -0.002(4) -0.003(4) C(3) 0.057(6) 0.063(7) 0.056(6) -0.008(6) 0.002(5) 0.004(5) C(4) 0.039(5) 0.054(6) 0.076(8) -0.009(5) -0.001(5) -0.013(6) C(5) 0.046(6) 0.072(7) 0.048(6) -0.001(5) -0.005(5) -0.023(5) C(6) 0.038(5) 0.047(5) 0.034(4) 0.006(4) -0.005(4) -0.016(4) C(7) 0.048(5) 0.066(6) 0.030(4) 0.030(5) -0.002(4) -0.003(4) C(8) 0.110(8) 0.136(9) 0.078(7) 0.081(7) -0.053(6) -0.068(7) C(9) 0.101(7) 0.125(8) 0.086(7) 0.069(6) -0.042(6) -0.052(6) C(10) 0.071(6) 0.093(7) 0.064(6) 0.033(5) -0.030(5) -0.014(5) C(11) 0.053(5) 0.070(6) 0.042(5) 0.004(5) -0.015(4) -0.004(4) C(12) 0.045(5) 0.057(6) 0.035(4) 0.005(4) -0.009(4) -0.003(4) C(13) 0.039(5) 0.040(5) 0.021(4) 0.002(4) 0.004(3) 0.001(3) C(14) 0.043(5) 0.057(6) 0.041(5) -0.001(5) 0.006(4) 0.005(5) C(15) 0.041(5) 0.063(7) 0.052(6) -0.004(5) 0.009(5) 0.014(5) C(16) 0.062(6) 0.041(5) 0.039(5) -0.004(5) 0.009(5) 0.004(4) C(17) 0.058(6) 0.040(5) 0.025(4) -0.000(4) 0.001(4) 0.001(4) C(18) 0.046(5) 0.046(5) 0.016(3) 0.009(4) -0.000(3) -0.004(3) C(19) 0.030(4) 0.028(4) 0.023(4) 0.007(3) 0.001(3) -0.007(3) C(20) 0.073(7) 0.076(8) 0.037(5) 0.025(6) -0.004(5) -0.011(5) C(21) 0.073(8) 0.092(10) 0.070(8) 0.040(7) 0.011(7) -0.011(7) C(22) 0.054(7) 0.073(8) 0.062(7) -0.001(6) 0.021(6) -0.024(6) C(23) 0.070(7) 0.065(7) 0.035(5) -0.001(6) 0.006(5) -0.021(5) C(24) 0.053(6) 0.061(6) 0.028(4) 0.003(5) -0.003(4) -0.006(4) C(25) 0.052(5) 0.040(5) 0.023(4) 0.006(4) -0.008(4) -0.004(4) C(26) 0.066(6) 0.043(5) 0.026(4) 0.008(5) -0.004(4) -0.008(4) C(27) 0.071(7) 0.033(5) 0.038(5) -0.001(5) -0.004(5) -0.006(4) C(28) 0.061(6) 0.048(6) 0.032(5) -0.009(5) -0.001(4) -0.004(4) C(29) 0.050(5) 0.049(5) 0.022(4) 0.002(4) -0.001(4) -0.001(4) C(30) 0.050(5) 0.036(5) 0.021(4) 0.009(4) -0.008(4) -0.003(3) C(31) 0.047(5) 0.029(4) 0.024(4) -0.009(4) -0.009(4) -0.006(3) C(32) 0.055(6) 0.047(5) 0.020(4) -0.003(5) -0.002(4) -0.004(4) C(33) 0.081(8) 0.042(5) 0.018(4) -0.011(5) -0.004(4) -0.000(4) C(34) 0.091(8) 0.052(6) 0.028(5) -0.007(6) -0.021(5) -0.002(4) C(35) 0.064(7) 0.058(7) 0.064(7) 0.014(6) -0.032(6) -0.017(6) C(36) 0.046(6) 0.065(7) 0.036(5) 0.011(5) -0.011(4) -0.009(5) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Pd(1) O(1) 2.071(5) yes . . Pd(1) O(3) 2.169(6) yes . 5_656 Pd(1) O(6) 2.047(5) yes . . Pd(1) C(1) 1.947(8) yes . . Pd(2) O(2) 2.037(6) yes . . Pd(2) O(3) 2.052(6) yes . . Pd(2) O(5) 2.184(6) yes . 5_656 Pd(2) C(13) 1.943(8) yes . . Pd(3) O(1) 2.215(6) yes . 5_656 Pd(3) O(4) 2.050(6) yes . . Pd(3) O(5) 2.057(5) yes . . Pd(3) C(25) 1.961(9) yes . . P(1) O(1) 1.537(6) yes . . P(1) O(2) 1.514(6) yes . . P(1) C(6) 1.782(9) yes . . P(1) C(7) 1.791(10) yes . . P(2) O(3) 1.553(6) yes . . P(2) O(4) 1.520(6) yes . . P(2) C(18) 1.789(9) yes . . P(2) C(19) 1.777(8) yes . . P(3) O(5) 1.545(6) yes . . P(3) O(6) 1.503(6) yes . . P(3) C(30) 1.791(8) yes . . P(3) C(31) 1.797(8) yes . . C(1) C(2) 1.387(12) yes . . C(1) C(6) 1.407(12) yes . . C(2) C(3) 1.380(14) yes . . C(3) C(4) 1.396(15) yes . . C(4) C(5) 1.380(15) yes . . C(5) C(6) 1.382(13) yes . . C(7) C(8) 1.343(17) yes . . C(7) C(12) 1.400(12) yes . . C(8) C(9) 1.39(2) yes . . C(9) C(10) 1.347(18) yes . . C(10) C(11) 1.327(16) yes . . C(11) C(12) 1.383(14) yes . . C(13) C(14) 1.403(13) yes . . C(13) C(18) 1.393(12) yes . . C(14) C(15) 1.371(15) yes . . C(15) C(16) 1.389(14) yes . . C(16) C(17) 1.368(14) yes . . C(17) C(18) 1.391(12) yes . . C(19) C(20) 1.370(13) yes . . C(19) C(24) 1.381(11) yes . . C(20) C(21) 1.399(16) yes . . C(21) C(22) 1.363(17) yes . . C(22) C(23) 1.354(15) yes . . C(23) C(24) 1.369(14) yes . . C(25) C(26) 1.380(13) yes . . C(25) C(30) 1.404(11) yes . . C(26) C(27) 1.389(13) yes . . C(27) C(28) 1.370(13) yes . . C(28) C(29) 1.360(13) yes . . C(29) C(30) 1.391(12) yes . . C(31) C(32) 1.375(11) yes . . C(31) C(36) 1.416(13) yes . . C(32) C(33) 1.384(12) yes . . C(33) C(34) 1.350(16) yes . . C(34) C(35) 1.373(15) yes . . C(35) C(36) 1.399(14) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(5) H(4) 0.950 no . . C(8) H(5) 0.950 no . . C(9) H(6) 0.950 no . . C(10) H(7) 0.950 no . . C(11) H(8) 0.950 no . . C(12) H(9) 0.950 no . . C(14) H(10) 0.950 no . . C(15) H(11) 0.950 no . . C(16) H(12) 0.950 no . . C(17) H(13) 0.950 no . . C(20) H(14) 0.950 no . . C(21) H(15) 0.950 no . . C(22) H(16) 0.950 no . . C(23) H(17) 0.950 no . . C(24) H(18) 0.950 no . . C(26) H(19) 0.950 no . . C(27) H(20) 0.950 no . . C(28) H(21) 0.950 no . . C(29) H(22) 0.950 no . . C(32) H(23) 0.950 no . . C(33) H(24) 0.950 no . . C(34) H(25) 0.950 no . . C(35) H(26) 0.950 no . . C(36) H(27) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) Pd(1) O(3) 93.1(2) yes . . 5_656 O(1) Pd(1) O(6) 173.7(2) yes . . . O(1) Pd(1) C(1) 87.4(3) yes . . . O(3) Pd(1) O(6) 86.1(2) yes 5_656 . . O(3) Pd(1) C(1) 176.0(3) yes 5_656 . . O(6) Pd(1) C(1) 93.8(3) yes . . . O(2) Pd(2) O(3) 178.6(2) yes . . . O(2) Pd(2) O(5) 86.1(3) yes . . 5_656 O(2) Pd(2) C(13) 94.3(3) yes . . . O(3) Pd(2) O(5) 94.2(2) yes . . 5_656 O(3) Pd(2) C(13) 85.6(3) yes . . . O(5) Pd(2) C(13) 173.7(3) yes 5_656 . . O(1) Pd(3) O(4) 86.3(2) yes 5_656 . . O(1) Pd(3) O(5) 93.2(2) yes 5_656 . . O(1) Pd(3) C(25) 175.6(3) yes 5_656 . . O(4) Pd(3) O(5) 176.4(2) yes . . . O(4) Pd(3) C(25) 93.8(3) yes . . . O(5) Pd(3) C(25) 87.0(3) yes . . . O(1) P(1) O(2) 116.6(3) yes . . . O(1) P(1) C(6) 102.7(4) yes . . . O(1) P(1) C(7) 108.5(4) yes . . . O(2) P(1) C(6) 113.3(4) yes . . . O(2) P(1) C(7) 105.9(4) yes . . . C(6) P(1) C(7) 109.7(4) yes . . . O(3) P(2) O(4) 115.1(3) yes . . . O(3) P(2) C(18) 101.1(4) yes . . . O(3) P(2) C(19) 109.1(3) yes . . . O(4) P(2) C(18) 114.2(4) yes . . . O(4) P(2) C(19) 106.6(4) yes . . . C(18) P(2) C(19) 110.8(4) yes . . . O(5) P(3) O(6) 115.8(3) yes . . . O(5) P(3) C(30) 102.6(4) yes . . . O(5) P(3) C(31) 109.1(4) yes . . . O(6) P(3) C(30) 112.7(4) yes . . . O(6) P(3) C(31) 104.4(4) yes . . . C(30) P(3) C(31) 112.4(4) yes . . . Pd(1) O(1) Pd(3) 114.3(3) yes . . 5_656 Pd(1) O(1) P(1) 115.6(3) yes . . . Pd(3) O(1) P(1) 123.9(3) yes 5_656 . . Pd(2) O(2) P(1) 121.7(3) yes . . . Pd(1) O(3) Pd(2) 115.0(3) yes 5_656 . . Pd(1) O(3) P(2) 123.5(3) yes 5_656 . . Pd(2) O(3) P(2) 117.4(3) yes . . . Pd(3) O(4) P(2) 115.1(4) yes . . . Pd(2) O(5) Pd(3) 121.7(3) yes 5_656 . . Pd(2) O(5) P(3) 120.2(3) yes 5_656 . . Pd(3) O(5) P(3) 117.2(3) yes . . . Pd(1) O(6) P(3) 114.4(3) yes . . . Pd(1) C(1) C(2) 124.9(7) yes . . . Pd(1) C(1) C(6) 115.9(6) yes . . . C(2) C(1) C(6) 119.1(8) yes . . . C(1) C(2) C(3) 120.0(9) yes . . . C(2) C(3) C(4) 121.0(10) yes . . . C(3) C(4) C(5) 119.2(10) yes . . . C(4) C(5) C(6) 120.3(9) yes . . . P(1) C(6) C(1) 116.7(7) yes . . . P(1) C(6) C(5) 122.9(7) yes . . . C(1) C(6) C(5) 120.4(8) yes . . . P(1) C(7) C(8) 122.4(8) yes . . . P(1) C(7) C(12) 119.5(7) yes . . . C(8) C(7) C(12) 118.0(10) yes . . . C(7) C(8) C(9) 120.8(12) yes . . . C(8) C(9) C(10) 120.4(13) yes . . . C(9) C(10) C(11) 120.0(12) yes . . . C(10) C(11) C(12) 121.0(10) yes . . . C(7) C(12) C(11) 119.7(9) yes . . . Pd(2) C(13) C(14) 122.3(7) yes . . . Pd(2) C(13) C(18) 118.4(6) yes . . . C(14) C(13) C(18) 118.8(8) yes . . . C(13) C(14) C(15) 119.4(9) yes . . . C(14) C(15) C(16) 121.5(9) yes . . . C(15) C(16) C(17) 119.7(9) yes . . . C(16) C(17) C(18) 119.8(9) yes . . . P(2) C(18) C(13) 115.5(7) yes . . . P(2) C(18) C(17) 123.6(7) yes . . . C(13) C(18) C(17) 120.8(8) yes . . . P(2) C(19) C(20) 121.0(6) yes . . . P(2) C(19) C(24) 121.9(6) yes . . . C(20) C(19) C(24) 117.1(8) yes . . . C(19) C(20) C(21) 121.5(9) yes . . . C(20) C(21) C(22) 119.0(11) yes . . . C(21) C(22) C(23) 120.4(11) yes . . . C(22) C(23) C(24) 120.1(9) yes . . . C(19) C(24) C(23) 121.9(9) yes . . . Pd(3) C(25) C(26) 124.6(7) yes . . . Pd(3) C(25) C(30) 116.5(6) yes . . . C(26) C(25) C(30) 118.8(8) yes . . . C(25) C(26) C(27) 119.6(8) yes . . . C(26) C(27) C(28) 121.4(9) yes . . . C(27) C(28) C(29) 119.5(9) yes . . . C(28) C(29) C(30) 120.6(8) yes . . . P(3) C(30) C(25) 116.5(6) yes . . . P(3) C(30) C(29) 123.4(6) yes . . . C(25) C(30) C(29) 120.0(8) yes . . . P(3) C(31) C(32) 120.3(7) yes . . . P(3) C(31) C(36) 119.5(6) yes . . . C(32) C(31) C(36) 120.1(8) yes . . . C(31) C(32) C(33) 119.5(9) yes . . . C(32) C(33) C(34) 121.5(9) yes . . . C(33) C(34) C(35) 120.0(9) yes . . . C(34) C(35) C(36) 121.0(10) yes . . . C(31) C(36) C(35) 117.8(9) yes . . . C(1) C(2) H(1) 120.024 no . . . C(3) C(2) H(1) 120.022 no . . . C(2) C(3) H(2) 119.514 no . . . C(4) C(3) H(2) 119.519 no . . . C(3) C(4) H(3) 120.393 no . . . C(5) C(4) H(3) 120.380 no . . . C(4) C(5) H(4) 119.831 no . . . C(6) C(5) H(4) 119.828 no . . . C(7) C(8) H(5) 119.558 no . . . C(9) C(8) H(5) 119.594 no . . . C(8) C(9) H(6) 119.804 no . . . C(10) C(9) H(6) 119.787 no . . . C(9) C(10) H(7) 120.020 no . . . C(11) C(10) H(7) 120.003 no . . . C(10) C(11) H(8) 119.476 no . . . C(12) C(11) H(8) 119.487 no . . . C(7) C(12) H(9) 120.148 no . . . C(11) C(12) H(9) 120.148 no . . . C(13) C(14) H(10) 120.330 no . . . C(15) C(14) H(10) 120.308 no . . . C(14) C(15) H(11) 119.278 no . . . C(16) C(15) H(11) 119.261 no . . . C(15) C(16) H(12) 120.156 no . . . C(17) C(16) H(12) 120.163 no . . . C(16) C(17) H(13) 120.128 no . . . C(18) C(17) H(13) 120.121 no . . . C(19) C(20) H(14) 119.259 no . . . C(21) C(20) H(14) 119.269 no . . . C(20) C(21) H(15) 120.467 no . . . C(22) C(21) H(15) 120.486 no . . . C(21) C(22) H(16) 119.799 no . . . C(23) C(22) H(16) 119.804 no . . . C(22) C(23) H(17) 119.953 no . . . C(24) C(23) H(17) 119.970 no . . . C(19) C(24) H(18) 119.077 no . . . C(23) C(24) H(18) 119.060 no . . . C(25) C(26) H(19) 120.209 no . . . C(27) C(26) H(19) 120.197 no . . . C(26) C(27) H(20) 119.267 no . . . C(28) C(27) H(20) 119.290 no . . . C(27) C(28) H(21) 120.231 no . . . C(29) C(28) H(21) 120.246 no . . . C(28) C(29) H(22) 119.707 no . . . C(30) C(29) H(22) 119.713 no . . . C(31) C(32) H(23) 120.240 no . . . C(33) C(32) H(23) 120.236 no . . . C(32) C(33) H(24) 119.228 no . . . C(34) C(33) H(24) 119.244 no . . . C(33) C(34) H(25) 119.999 no . . . C(35) C(34) H(25) 120.013 no . . . C(34) C(35) H(26) 119.498 no . . . C(36) C(35) H(26) 119.492 no . . . C(31) C(36) H(27) 121.112 no . . . C(35) C(36) H(27) 121.112 no . . . #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment '773372.cif' data_han1d _database_code_depnum_ccdc_archive 'CCDC 773372' #TrackingRef '773372.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H36 O3 P4 Pd, C H2 Cl2' _chemical_formula_sum 'C31 H38 Cl2 O3 P4 Pd' _chemical_formula_weight 759.79 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.8490(9) _cell_length_b 11.5995(7) _cell_length_c 19.2145(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.2570(10) _cell_angle_gamma 90.00 _cell_volume 3304.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 7716 _cell_measurement_theta_min 2.436 _cell_measurement_theta_max 28.251 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7640 _exptl_absorpt_correction_T_max 0.9541 _exptl_absorpt_process_details sadabs _exptl_special_details ; Two restrains were added ; DFIX 1.1 0.02 O2 H1 DFIX 2.14 0.01 P4 H1 ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating unit' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 566 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 529 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 20039 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 28.25 _reflns_number_total 7503 _reflns_number_gt 6939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+2.5031P] 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 7503 _refine_ls_number_parameters 377 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.14421(12) 0.47915(15) 0.19757(9) 0.0220(3) Uani 1 1 d . . . C2 C 0.05525(12) 0.51217(16) 0.20786(10) 0.0266(4) Uani 1 1 d . . . H2 H 0.0126 0.4548 0.2188 0.032 Uiso 1 1 calc R . . C3 C 0.02745(13) 0.62624(17) 0.20253(11) 0.0310(4) Uani 1 1 d . . . H3 H -0.0334 0.6460 0.2099 0.037 Uiso 1 1 calc R . . C4 C 0.08856(14) 0.71157(17) 0.18648(11) 0.0322(4) Uani 1 1 d . . . H4 H 0.0703 0.7900 0.1840 0.039 Uiso 1 1 calc R . . C5 C 0.17625(13) 0.68122(15) 0.17419(11) 0.0276(4) Uani 1 1 d . . . H5 H 0.2177 0.7391 0.1620 0.033 Uiso 1 1 calc R . . C6 C 0.20484(11) 0.56627(15) 0.17946(9) 0.0219(3) Uani 1 1 d . . . C7 C 0.02906(13) 0.29790(16) 0.08007(11) 0.0285(4) Uani 1 1 d . . . C8 C 0.00047(16) 0.35293(18) 0.01835(12) 0.0385(5) Uani 1 1 d . . . H8 H 0.0430 0.3724 -0.0149 0.046 Uiso 1 1 calc R . . C9 C -0.09066(19) 0.3797(2) 0.00512(16) 0.0536(7) Uani 1 1 d . . . H9 H -0.1098 0.4177 -0.0369 0.064 Uiso 1 1 calc R . . C10 C -0.15259(18) 0.3512(2) 0.05259(18) 0.0579(8) Uani 1 1 d . . . H10 H -0.2143 0.3706 0.0436 0.070 Uiso 1 1 calc R . . C11 C -0.12527(17) 0.2943(2) 0.11348(17) 0.0518(7) Uani 1 1 d . . . H11 H -0.1685 0.2733 0.1458 0.062 Uiso 1 1 calc R . . C12 C -0.03432(15) 0.2678(2) 0.12749(13) 0.0389(5) Uani 1 1 d . . . H12 H -0.0157 0.2291 0.1695 0.047 Uiso 1 1 calc R . . C13 C 0.16869(13) 0.12710(15) 0.07452(9) 0.0250(4) Uani 1 1 d . . . C14 C 0.10230(14) 0.04220(16) 0.06710(10) 0.0299(4) Uani 1 1 d . . . H14 H 0.0412 0.0609 0.0740 0.036 Uiso 1 1 calc R . . C15 C 0.12564(16) -0.07000(17) 0.04951(11) 0.0369(5) Uani 1 1 d . . . H15 H 0.0802 -0.1275 0.0441 0.044 Uiso 1 1 calc R . . C16 C 0.21426(17) -0.09810(18) 0.03987(11) 0.0396(5) Uani 1 1 d . . . H16 H 0.2298 -0.1750 0.0285 0.048 Uiso 1 1 calc R . . C17 C 0.28045(16) -0.01451(19) 0.04671(11) 0.0380(5) Uani 1 1 d . . . H17 H 0.3415 -0.0340 0.0399 0.046 Uiso 1 1 calc R . . C18 C 0.25790(14) 0.09780(17) 0.06345(10) 0.0308(4) Uani 1 1 d . . . H18 H 0.3035 0.1552 0.0674 0.037 Uiso 1 1 calc R . . C19 C 0.38216(12) 0.65961(16) 0.16025(10) 0.0257(4) Uani 1 1 d . . . C20 C 0.41818(14) 0.70538(18) 0.10104(11) 0.0322(4) Uani 1 1 d . . . H20 H 0.4091 0.6670 0.0575 0.039 Uiso 1 1 calc R . . C21 C 0.46760(15) 0.80742(19) 0.10545(13) 0.0382(5) Uani 1 1 d . . . H21 H 0.4930 0.8376 0.0650 0.046 Uiso 1 1 calc R . . C22 C 0.47994(14) 0.86486(18) 0.16793(13) 0.0382(5) Uani 1 1 d . . . H22 H 0.5131 0.9349 0.1704 0.046 Uiso 1 1 calc R . . C23 C 0.44407(15) 0.82063(18) 0.22697(13) 0.0369(5) Uani 1 1 d . . . H23 H 0.4524 0.8604 0.2701 0.044 Uiso 1 1 calc R . . C24 C 0.39590(14) 0.71818(18) 0.22337(11) 0.0321(4) Uani 1 1 d . . . H24 H 0.3720 0.6876 0.2643 0.039 Uiso 1 1 calc R . . C25 C 0.27502(14) 0.25913(18) 0.38110(10) 0.0314(4) Uani 1 1 d . . . H25A H 0.3403 0.2705 0.3756 0.038 Uiso 1 1 calc R . . H25B H 0.2639 0.2651 0.4313 0.038 Uiso 1 1 calc R . . C26 C 0.24639(15) 0.14024(18) 0.35382(10) 0.0320(4) Uani 1 1 d . . . H26A H 0.1851 0.1221 0.3684 0.038 Uiso 1 1 calc R . . H26B H 0.2884 0.0810 0.3737 0.038 Uiso 1 1 calc R . . C27 C 0.10815(14) 0.3847(2) 0.37884(11) 0.0355(4) Uani 1 1 d . . . H27A H 0.1237 0.4096 0.4268 0.053 Uiso 1 1 calc R . . H27B H 0.0770 0.3103 0.3795 0.053 Uiso 1 1 calc R . . H27C H 0.0686 0.4422 0.3555 0.053 Uiso 1 1 calc R . . C28 C 0.27022(16) 0.50339(19) 0.35110(11) 0.0361(5) Uani 1 1 d . . . H28A H 0.2343 0.5685 0.3325 0.054 Uiso 1 1 calc R . . H28B H 0.3283 0.5019 0.3294 0.054 Uiso 1 1 calc R . . H28C H 0.2805 0.5120 0.4017 0.054 Uiso 1 1 calc R . . C29 C 0.20725(15) -0.00646(17) 0.23689(11) 0.0337(4) Uani 1 1 d . . . H29A H 0.2135 -0.0214 0.1872 0.051 Uiso 1 1 calc R . . H29B H 0.1437 -0.0133 0.2475 0.051 Uiso 1 1 calc R . . H29C H 0.2431 -0.0627 0.2646 0.051 Uiso 1 1 calc R . . C30 C 0.36630(13) 0.13329(19) 0.24215(12) 0.0352(4) Uani 1 1 d . . . H30A H 0.3967 0.0780 0.2741 0.053 Uiso 1 1 calc R . . H30B H 0.3927 0.2100 0.2499 0.053 Uiso 1 1 calc R . . H30C H 0.3739 0.1094 0.1939 0.053 Uiso 1 1 calc R . . C31 C 0.52095(19) 0.8222(2) 0.41803(15) 0.0509(6) Uani 1 1 d . . . H31A H 0.5595 0.8319 0.4614 0.061 Uiso 1 1 calc R . . H31B H 0.5587 0.8370 0.3781 0.061 Uiso 1 1 calc R . . Cl1 Cl 0.48146(6) 0.67914(7) 0.41332(4) 0.0661(2) Uani 1 1 d . . . Cl2 Cl 0.43378(7) 0.92385(9) 0.41701(4) 0.0790(3) Uani 1 1 d . . . O1 O 0.19943(10) 0.34671(12) 0.04643(7) 0.0307(3) Uani 1 1 d . . . O2 O 0.31067(9) 0.49289(13) 0.07954(7) 0.0324(3) Uani 1 1 d D . . H1 H 0.2600(13) 0.4333(18) 0.0690(8) 0.038 Uiso 1 1 d D . . O3 O 0.35946(9) 0.43985(12) 0.20630(8) 0.0321(3) Uani 1 1 d . . . P1 P 0.24707(3) 0.13798(4) 0.25798(2) 0.02335(10) Uani 1 1 d . . . P2 P 0.21033(3) 0.37012(4) 0.33216(2) 0.02353(10) Uani 1 1 d . . . P3 P 0.14896(3) 0.27573(4) 0.10060(2) 0.02265(10) Uani 1 1 d . . . P4 P 0.31806(3) 0.52713(4) 0.15722(2) 0.02321(10) Uani 1 1 d D . . Pd1 Pd 0.186485(8) 0.312521(11) 0.217352(6) 0.01950(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0254(8) 0.0193(8) 0.0212(8) -0.0012(6) -0.0002(6) 0.0014(6) C2 0.0244(8) 0.0244(9) 0.0313(9) -0.0004(7) 0.0021(7) -0.0006(7) C3 0.0236(9) 0.0298(10) 0.0395(11) -0.0019(8) 0.0015(8) 0.0058(7) C4 0.0321(10) 0.0219(8) 0.0423(11) 0.0000(8) -0.0022(8) 0.0073(7) C5 0.0290(9) 0.0210(8) 0.0324(10) 0.0033(7) -0.0003(8) -0.0003(7) C6 0.0225(8) 0.0209(8) 0.0221(8) 0.0002(6) 0.0000(6) 0.0014(6) C7 0.0329(10) 0.0202(8) 0.0316(10) -0.0053(7) -0.0066(8) -0.0003(7) C8 0.0496(12) 0.0235(9) 0.0402(12) -0.0004(8) -0.0157(10) -0.0005(8) C9 0.0572(15) 0.0290(11) 0.0703(18) -0.0058(11) -0.0350(14) 0.0068(10) C10 0.0400(13) 0.0375(13) 0.093(2) -0.0254(14) -0.0259(14) 0.0077(10) C11 0.0347(12) 0.0456(13) 0.0751(19) -0.0247(13) 0.0038(12) -0.0043(10) C12 0.0367(11) 0.0375(11) 0.0422(12) -0.0068(9) 0.0004(9) -0.0028(9) C13 0.0346(9) 0.0214(8) 0.0188(8) -0.0012(6) -0.0010(7) -0.0016(7) C14 0.0377(10) 0.0246(9) 0.0271(9) 0.0001(7) -0.0009(8) -0.0047(8) C15 0.0563(13) 0.0221(9) 0.0316(10) -0.0010(8) -0.0031(9) -0.0084(9) C16 0.0643(15) 0.0229(9) 0.0312(10) -0.0044(8) -0.0010(10) 0.0063(9) C17 0.0459(12) 0.0359(11) 0.0326(11) -0.0021(9) 0.0039(9) 0.0108(9) C18 0.0365(10) 0.0282(9) 0.0276(9) -0.0009(7) 0.0002(8) -0.0018(8) C19 0.0220(8) 0.0258(8) 0.0293(9) -0.0006(7) 0.0000(7) -0.0010(7) C20 0.0311(10) 0.0339(10) 0.0318(10) -0.0005(8) 0.0037(8) -0.0032(8) C21 0.0343(11) 0.0363(11) 0.0445(13) 0.0075(9) 0.0071(9) -0.0061(8) C22 0.0297(10) 0.0271(10) 0.0572(14) 0.0015(9) -0.0031(9) -0.0048(8) C23 0.0364(11) 0.0318(10) 0.0416(12) -0.0080(9) -0.0060(9) -0.0016(8) C24 0.0335(10) 0.0330(10) 0.0295(10) -0.0018(8) -0.0006(8) -0.0034(8) C25 0.0363(10) 0.0355(10) 0.0220(9) 0.0005(8) -0.0030(8) 0.0044(8) C26 0.0405(11) 0.0299(10) 0.0256(9) 0.0055(8) 0.0018(8) 0.0052(8) C27 0.0324(10) 0.0461(12) 0.0285(10) -0.0063(9) 0.0066(8) 0.0010(9) C28 0.0481(12) 0.0336(11) 0.0265(10) -0.0047(8) -0.0002(8) -0.0115(9) C29 0.0432(11) 0.0210(9) 0.0368(10) 0.0023(8) 0.0016(9) -0.0023(8) C30 0.0292(10) 0.0354(11) 0.0413(11) 0.0001(9) 0.0036(8) 0.0035(8) C31 0.0490(14) 0.0512(15) 0.0529(15) 0.0086(12) 0.0046(12) -0.0055(11) Cl1 0.0866(5) 0.0624(4) 0.0504(4) -0.0013(3) 0.0133(4) -0.0248(4) Cl2 0.0902(6) 0.0911(6) 0.0574(4) 0.0148(4) 0.0181(4) 0.0353(5) O1 0.0448(8) 0.0260(7) 0.0211(6) 0.0006(5) 0.0014(6) -0.0103(6) O2 0.0342(7) 0.0342(7) 0.0293(7) -0.0073(6) 0.0075(6) -0.0092(6) O3 0.0283(7) 0.0279(7) 0.0404(8) 0.0057(6) 0.0031(6) 0.0060(5) P1 0.0271(2) 0.0191(2) 0.0239(2) 0.00205(17) 0.00127(17) 0.00140(16) P2 0.0271(2) 0.0244(2) 0.0191(2) -0.00194(17) 0.00167(17) -0.00053(17) P3 0.0299(2) 0.0182(2) 0.0196(2) -0.00037(16) -0.00138(17) -0.00239(17) P4 0.0231(2) 0.0210(2) 0.0257(2) -0.00059(17) 0.00291(17) -0.00045(16) Pd1 0.02348(8) 0.01658(7) 0.01839(7) -0.00016(4) 0.00071(5) 0.00052(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 C1 C2 1.400(2) . ? C1 C6 1.410(2) . ? C1 Pd1 2.0609(17) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.401(2) . ? C5 H5 0.9500 . ? C6 P4 1.8158(18) . ? C7 C8 1.392(3) . ? C7 C12 1.391(3) . ? C7 P3 1.820(2) . ? C8 C9 1.397(3) . ? C8 H8 0.9500 . ? C9 C10 1.372(5) . ? C9 H9 0.9500 . ? C10 C11 1.384(5) . ? C10 H10 0.9500 . ? C11 C12 1.396(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.395(3) . ? C13 C18 1.396(3) . ? C13 P3 1.8236(19) . ? C14 C15 1.393(3) . ? C14 H14 0.9500 . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 C18 1.387(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.390(3) . ? C19 C24 1.395(3) . ? C19 P4 1.8068(19) . ? C20 C21 1.393(3) . ? C20 H20 0.9500 . ? C21 C22 1.376(3) . ? C21 H21 0.9500 . ? C22 C23 1.379(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.527(3) . ? C25 P2 1.834(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 P1 1.842(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 P2 1.814(2) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 P2 1.810(2) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 P1 1.815(2) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 P1 1.814(2) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 Cl2 1.750(3) . ? C31 Cl1 1.761(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? O1 P3 1.5530(14) . ? O2 P4 1.5423(14) . ? O2 H1 1.033(13) . ? O3 P4 1.4921(14) . ? P1 Pd1 2.3320(5) . ? P2 Pd1 2.3129(5) . ? P3 Pd1 2.3201(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117.35(16) . . ? C2 C1 Pd1 120.70(13) . . ? C6 C1 Pd1 121.70(12) . . ? C3 C2 C1 121.96(17) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 120.01(18) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.35(18) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.97(18) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 120.31(16) . . ? C5 C6 P4 120.11(14) . . ? C1 C6 P4 119.45(13) . . ? C8 C7 C12 119.2(2) . . ? C8 C7 P3 119.80(17) . . ? C12 C7 P3 120.82(16) . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 120.1(2) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C18 118.94(18) . . ? C14 C13 P3 124.88(15) . . ? C18 C13 P3 116.15(14) . . ? C13 C14 C15 120.0(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.04(19) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.51(19) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C20 C19 C24 118.79(18) . . ? C20 C19 P4 121.67(15) . . ? C24 C19 P4 119.54(15) . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.5(2) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 120.0(2) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 120.7(2) . . ? C23 C24 H24 119.7 . . ? C19 C24 H24 119.7 . . ? C26 C25 P2 109.30(13) . . ? C26 C25 H25A 109.8 . . ? P2 C25 H25A 109.8 . . ? C26 C25 H25B 109.8 . . ? P2 C25 H25B 109.8 . . ? H25A C25 H25B 108.3 . . ? C25 C26 P1 109.80(13) . . ? C25 C26 H26A 109.7 . . ? P1 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? P1 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? P2 C27 H27A 109.5 . . ? P2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? P2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? P2 C28 H28A 109.5 . . ? P2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? P2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? P1 C29 H29A 109.5 . . ? P1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? P1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? P1 C30 H30A 109.5 . . ? P1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? P1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? Cl2 C31 Cl1 112.97(15) . . ? Cl2 C31 H31A 109.0 . . ? Cl1 C31 H31A 109.0 . . ? Cl2 C31 H31B 109.0 . . ? Cl1 C31 H31B 109.0 . . ? H31A C31 H31B 107.8 . . ? P4 O2 H1 111.9(9) . . ? C29 P1 C30 104.10(10) . . ? C29 P1 C26 102.48(10) . . ? C30 P1 C26 103.23(10) . . ? C29 P1 Pd1 127.74(7) . . ? C30 P1 Pd1 109.36(7) . . ? C26 P1 Pd1 107.36(7) . . ? C28 P2 C27 103.65(11) . . ? C28 P2 C25 105.04(10) . . ? C27 P2 C25 103.93(10) . . ? C28 P2 Pd1 119.03(7) . . ? C27 P2 Pd1 114.31(7) . . ? C25 P2 Pd1 109.49(7) . . ? O1 P3 C7 106.45(9) . . ? O1 P3 C13 103.06(8) . . ? C7 P3 C13 104.15(8) . . ? O1 P3 Pd1 116.87(5) . . ? C7 P3 Pd1 111.22(7) . . ? C13 P3 Pd1 113.96(6) . . ? O3 P4 O2 116.17(9) . . ? O3 P4 C19 111.06(9) . . ? O2 P4 C19 104.99(8) . . ? O3 P4 C6 112.00(8) . . ? O2 P4 C6 106.04(8) . . ? C19 P4 C6 105.84(8) . . ? C1 Pd1 P2 86.19(5) . . ? C1 Pd1 P3 86.58(5) . . ? P2 Pd1 P3 172.173(17) . . ? C1 Pd1 P1 169.63(5) . . ? P2 Pd1 P1 84.044(17) . . ? P3 Pd1 P1 103.349(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.8(3) . . . . ? Pd1 C1 C2 C3 172.66(15) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 1.6(3) . . . . ? C3 C4 C5 C6 -1.7(3) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? C4 C5 C6 P4 175.73(16) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? Pd1 C1 C6 C5 -172.63(14) . . . . ? C2 C1 C6 P4 -174.09(13) . . . . ? Pd1 C1 C6 P4 11.6(2) . . . . ? C12 C7 C8 C9 1.4(3) . . . . ? P3 C7 C8 C9 -174.18(16) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C9 C10 C11 -0.9(4) . . . . ? C9 C10 C11 C12 1.3(4) . . . . ? C8 C7 C12 C11 -1.0(3) . . . . ? P3 C7 C12 C11 174.52(17) . . . . ? C10 C11 C12 C7 -0.3(3) . . . . ? C18 C13 C14 C15 0.6(3) . . . . ? P3 C13 C14 C15 -177.47(15) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C16 C17 C18 C13 0.9(3) . . . . ? C14 C13 C18 C17 -1.3(3) . . . . ? P3 C13 C18 C17 176.92(16) . . . . ? C24 C19 C20 C21 0.5(3) . . . . ? P4 C19 C20 C21 -179.70(16) . . . . ? C19 C20 C21 C22 -1.1(3) . . . . ? C20 C21 C22 C23 0.7(3) . . . . ? C21 C22 C23 C24 0.2(3) . . . . ? C22 C23 C24 C19 -0.8(3) . . . . ? C20 C19 C24 C23 0.4(3) . . . . ? P4 C19 C24 C23 -179.34(16) . . . . ? P2 C25 C26 P1 49.04(17) . . . . ? C25 C26 P1 C29 -177.76(14) . . . . ? C25 C26 P1 C30 74.28(16) . . . . ? C25 C26 P1 Pd1 -41.21(15) . . . . ? C26 C25 P2 C28 -164.55(14) . . . . ? C26 C25 P2 C27 86.88(15) . . . . ? C26 C25 P2 Pd1 -35.64(15) . . . . ? C8 C7 P3 O1 10.03(18) . . . . ? C12 C7 P3 O1 -165.45(16) . . . . ? C8 C7 P3 C13 -98.47(17) . . . . ? C12 C7 P3 C13 86.04(17) . . . . ? C8 C7 P3 Pd1 138.36(15) . . . . ? C12 C7 P3 Pd1 -37.13(18) . . . . ? C14 C13 P3 O1 -132.68(16) . . . . ? C18 C13 P3 O1 49.23(16) . . . . ? C14 C13 P3 C7 -21.69(18) . . . . ? C18 C13 P3 C7 160.22(15) . . . . ? C14 C13 P3 Pd1 99.68(16) . . . . ? C18 C13 P3 Pd1 -78.42(15) . . . . ? C20 C19 P4 O3 122.27(16) . . . . ? C24 C19 P4 O3 -57.95(18) . . . . ? C20 C19 P4 O2 -4.05(18) . . . . ? C24 C19 P4 O2 175.73(15) . . . . ? C20 C19 P4 C6 -115.97(17) . . . . ? C24 C19 P4 C6 63.82(17) . . . . ? C5 C6 P4 O3 140.14(15) . . . . ? C1 C6 P4 O3 -44.04(17) . . . . ? C5 C6 P4 O2 -92.20(16) . . . . ? C1 C6 P4 O2 83.63(15) . . . . ? C5 C6 P4 C19 18.98(18) . . . . ? C1 C6 P4 C19 -165.20(14) . . . . ? C2 C1 Pd1 P2 -84.30(14) . . . . ? C6 C1 Pd1 P2 89.87(14) . . . . ? C2 C1 Pd1 P3 92.71(14) . . . . ? C6 C1 Pd1 P3 -93.12(14) . . . . ? C2 C1 Pd1 P1 -103.9(3) . . . . ? C6 C1 Pd1 P1 70.3(3) . . . . ? C28 P2 Pd1 C1 -47.40(10) . . . . ? C27 P2 Pd1 C1 75.76(10) . . . . ? C25 P2 Pd1 C1 -168.14(9) . . . . ? C28 P2 Pd1 P1 129.12(9) . . . . ? C27 P2 Pd1 P1 -107.72(9) . . . . ? C25 P2 Pd1 P1 8.38(7) . . . . ? O1 P3 Pd1 C1 60.36(8) . . . . ? C7 P3 Pd1 C1 -62.13(8) . . . . ? C13 P3 Pd1 C1 -179.49(8) . . . . ? O1 P3 Pd1 P1 -116.61(7) . . . . ? C7 P3 Pd1 P1 120.90(7) . . . . ? C13 P3 Pd1 P1 3.55(7) . . . . ? C29 P1 Pd1 C1 156.5(3) . . . . ? C30 P1 Pd1 C1 -76.8(3) . . . . ? C26 P1 Pd1 C1 34.6(3) . . . . ? C29 P1 Pd1 P2 136.81(9) . . . . ? C30 P1 Pd1 P2 -96.43(8) . . . . ? C26 P1 Pd1 P2 14.92(7) . . . . ? C29 P1 Pd1 P3 -40.58(9) . . . . ? C30 P1 Pd1 P3 86.18(8) . . . . ? C26 P1 Pd1 P3 -162.47(7) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.22 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.330 _refine_diff_density_min -1.142 _refine_diff_density_rms 0.087