# 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_msb053 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 Cl N O2 P Se' _chemical_formula_weight 384.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Se Se -0.0929 2.2259 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8148(8) _cell_length_b 9.8338(14) _cell_length_c 9.8496(17) _cell_angle_alpha 80.830(13) _cell_angle_beta 74.747(11) _cell_angle_gamma 76.426(10) _cell_volume 796.36(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3013 _cell_measurement_theta_min 3.5545 _cell_measurement_theta_max 32.6860 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 2.628 _exptl_absorpt_correction_T_min 0.5832 _exptl_absorpt_correction_T_max 0.6939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5781 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2780 _reflns_number_gt 1955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.1106P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2780 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 P1 P 0.68619(14) 0.26091(11) 1.19998(12) 0.0485(3) Uani 1 1 d . . . Se1 Se 0.46489(6) 0.27342(6) 1.33884(6) 0.0762(3) Uani 1 1 d . . . Cl1 Cl 0.9327(2) -0.17514(15) 1.49171(19) 0.0989(6) Uani 1 1 d . . . O1 O 0.6813(4) 0.3216(3) 1.0393(3) 0.0567(8) Uani 1 1 d . . . O2 O 0.8513(5) -0.1015(4) 1.0679(4) 0.0805(12) Uani 1 1 d . . . N1 N 0.7924(4) 0.0965(4) 1.1760(4) 0.0534(9) Uani 1 1 d . . . C1 C 0.8217(5) 0.3552(4) 1.2337(5) 0.0512(11) Uani 1 1 d . . . C2 C 0.7700(6) 0.4373(5) 1.3453(5) 0.0627(13) Uani 1 1 d . . . H2 H 0.6671 0.4396 1.4078 0.075 Uiso 1 1 calc R . . C3 C 0.8749(7) 0.5168(6) 1.3628(7) 0.0771(16) Uani 1 1 d . . . H3 H 0.8419 0.5761 1.4369 0.093 Uiso 1 1 calc R . . C4 C 1.0234(7) 0.5101(5) 1.2750(7) 0.0751(15) Uani 1 1 d . . . H4 H 1.0932 0.5640 1.2896 0.090 Uiso 1 1 calc R . . C5 C 1.0745(7) 0.4268(6) 1.1655(6) 0.0732(14) Uani 1 1 d . . . H5 H 1.1786 0.4230 1.1049 0.088 Uiso 1 1 calc R . . C6 C 0.9723(6) 0.3485(5) 1.1447(5) 0.0618(12) Uani 1 1 d . . . H6 H 1.0059 0.2905 1.0694 0.074 Uiso 1 1 calc R . . C7 C 0.6486(5) 0.2423(5) 0.9499(5) 0.0502(10) Uani 1 1 d . . . C8 C 0.5727(7) 0.3141(6) 0.8456(6) 0.0737(15) Uani 1 1 d . . . H8 H 0.5385 0.4135 0.8392 0.088 Uiso 1 1 calc R . . C9 C 0.5483(8) 0.2361(7) 0.7506(6) 0.0847(18) Uani 1 1 d . . . H9 H 0.4999 0.2830 0.6757 0.102 Uiso 1 1 calc R . . C10 C 0.5927(7) 0.0927(6) 0.7630(6) 0.0730(15) Uani 1 1 d . . . H10 H 0.5712 0.0406 0.6994 0.088 Uiso 1 1 calc R . . C11 C 0.6678(6) 0.0242(5) 0.8665(5) 0.0602(12) Uani 1 1 d . . . H11 H 0.7005 -0.0753 0.8726 0.072 Uiso 1 1 calc R . . C12 C 0.6977(5) 0.0974(4) 0.9636(5) 0.0478(10) Uani 1 1 d . . . C13 C 0.7864(6) 0.0213(5) 1.0703(5) 0.0548(11) Uani 1 1 d . . . C14 C 0.8905(8) 0.0172(6) 1.2803(6) 0.0755(15) Uani 1 1 d . . . H14A H 0.9920 -0.0392 1.2292 0.091 Uiso 1 1 calc R . . H14B H 0.9172 0.0844 1.3308 0.091 Uiso 1 1 calc R . . C15 C 0.7978(8) -0.0739(8) 1.3799(7) 0.0934(19) Uani 1 1 d . . . H15A H 0.7642 -0.1375 1.3302 0.112 Uiso 1 1 calc R . . H15B H 0.7007 -0.0182 1.4379 0.112 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 P1 0.0603(7) 0.0367(6) 0.0510(7) -0.0110(5) -0.0171(6) -0.0057(5) Se1 0.0695(4) 0.0678(4) 0.0861(5) -0.0208(3) 0.0015(3) -0.0175(3) Cl1 0.1650(17) 0.0555(8) 0.1050(12) 0.0117(7) -0.0904(12) -0.0253(9) O1 0.076(2) 0.0434(16) 0.057(2) -0.0049(14) -0.0258(17) -0.0130(15) O2 0.112(3) 0.0472(19) 0.086(3) -0.0316(18) -0.043(2) 0.0144(19) N1 0.070(2) 0.0407(19) 0.054(2) -0.0140(16) -0.0272(19) -0.0009(17) C1 0.066(3) 0.038(2) 0.054(3) -0.0128(19) -0.023(2) -0.005(2) C2 0.069(3) 0.056(3) 0.065(3) -0.024(2) -0.016(3) -0.004(2) C3 0.098(4) 0.058(3) 0.094(4) -0.029(3) -0.044(4) -0.014(3) C4 0.083(4) 0.061(3) 0.098(5) -0.012(3) -0.040(4) -0.023(3) C5 0.074(3) 0.078(4) 0.077(4) -0.006(3) -0.024(3) -0.027(3) C6 0.068(3) 0.058(3) 0.059(3) -0.015(2) -0.014(3) -0.007(2) C7 0.054(2) 0.054(3) 0.047(3) -0.008(2) -0.014(2) -0.017(2) C8 0.098(4) 0.063(3) 0.075(4) -0.002(3) -0.044(3) -0.021(3) C9 0.106(5) 0.098(5) 0.070(4) -0.003(3) -0.051(4) -0.028(4) C10 0.082(3) 0.088(4) 0.063(3) -0.024(3) -0.025(3) -0.026(3) C11 0.065(3) 0.061(3) 0.062(3) -0.020(2) -0.016(3) -0.018(2) C12 0.051(2) 0.050(2) 0.044(2) -0.0132(19) -0.006(2) -0.015(2) C13 0.065(3) 0.048(3) 0.052(3) -0.015(2) -0.011(2) -0.008(2) C14 0.097(4) 0.071(3) 0.071(4) -0.015(3) -0.022(3) -0.034(3) C15 0.087(4) 0.119(5) 0.081(4) -0.017(4) -0.022(4) -0.029(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 P1 O1 1.608(3) . ? P1 N1 1.686(3) . ? P1 C1 1.796(4) . ? P1 Se1 2.0563(13) . ? Cl1 C15 1.845(6) . ? O1 C7 1.388(5) . ? O2 C13 1.210(6) . ? N1 C13 1.388(5) . ? N1 C14 1.518(7) . ? C1 C6 1.379(7) . ? C1 C2 1.383(6) . ? C2 C3 1.401(7) . ? C2 H2 0.9500 . ? C3 C4 1.359(8) . ? C3 H3 0.9500 . ? C4 C5 1.375(8) . ? C4 H4 0.9500 . ? C5 C6 1.385(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.382(6) . ? C7 C12 1.384(6) . ? C8 C9 1.387(7) . ? C8 H8 0.9500 . ? C9 C10 1.367(8) . ? C9 H9 0.9500 . ? C10 C11 1.363(7) . ? C10 H10 0.9500 . ? C11 C12 1.394(6) . ? C11 H11 0.9500 . ? C12 C13 1.478(6) . ? C14 C15 1.440(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 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 O1 P1 N1 100.35(17) . . ? O1 P1 C1 101.34(19) . . ? N1 P1 C1 105.75(19) . . ? O1 P1 Se1 114.79(13) . . ? N1 P1 Se1 115.28(15) . . ? C1 P1 Se1 117.13(16) . . ? C7 O1 P1 121.0(3) . . ? C13 N1 C14 115.9(4) . . ? C13 N1 P1 123.5(3) . . ? C14 N1 P1 120.3(3) . . ? C6 C1 C2 121.6(4) . . ? C6 C1 P1 119.3(3) . . ? C2 C1 P1 119.0(4) . . ? C1 C2 C3 117.5(5) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 121.2(5) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 119.2(5) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 119.6(5) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C12 122.6(4) . . ? C8 C7 O1 117.4(4) . . ? C12 C7 O1 119.9(4) . . ? C7 C8 C9 117.7(5) . . ? C7 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? C10 C9 C8 121.0(5) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 120.2(5) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 121.3(5) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C7 C12 C11 117.2(4) . . ? C7 C12 C13 122.6(4) . . ? C11 C12 C13 120.1(4) . . ? O2 C13 N1 120.4(4) . . ? O2 C13 C12 122.4(4) . . ? N1 C13 C12 117.2(4) . . ? C15 C14 N1 108.7(5) . . ? C15 C14 H14A 109.9 . . ? N1 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? N1 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C14 C15 Cl1 105.3(4) . . ? C14 C15 H15A 110.7 . . ? Cl1 C15 H15A 110.7 . . ? C14 C15 H15B 110.7 . . ? Cl1 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? 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 N1 P1 O1 C7 44.3(3) . . . . ? C1 P1 O1 C7 152.9(3) . . . . ? Se1 P1 O1 C7 -79.9(3) . . . . ? O1 P1 N1 C13 -32.1(4) . . . . ? C1 P1 N1 C13 -137.1(4) . . . . ? Se1 P1 N1 C13 91.8(4) . . . . ? O1 P1 N1 C14 153.5(4) . . . . ? C1 P1 N1 C14 48.5(4) . . . . ? Se1 P1 N1 C14 -82.6(4) . . . . ? O1 P1 C1 C6 -55.2(4) . . . . ? N1 P1 C1 C6 49.1(4) . . . . ? Se1 P1 C1 C6 179.1(3) . . . . ? O1 P1 C1 C2 122.3(4) . . . . ? N1 P1 C1 C2 -133.4(4) . . . . ? Se1 P1 C1 C2 -3.4(4) . . . . ? C6 C1 C2 C3 1.6(7) . . . . ? P1 C1 C2 C3 -175.8(4) . . . . ? C1 C2 C3 C4 -1.6(8) . . . . ? C2 C3 C4 C5 0.8(9) . . . . ? C3 C4 C5 C6 0.0(9) . . . . ? C2 C1 C6 C5 -0.8(7) . . . . ? P1 C1 C6 C5 176.6(4) . . . . ? C4 C5 C6 C1 0.0(8) . . . . ? P1 O1 C7 C8 149.9(4) . . . . ? P1 O1 C7 C12 -32.8(5) . . . . ? C12 C7 C8 C9 -1.0(8) . . . . ? O1 C7 C8 C9 176.2(5) . . . . ? C7 C8 C9 C10 2.3(9) . . . . ? C8 C9 C10 C11 -2.6(9) . . . . ? C9 C10 C11 C12 1.5(8) . . . . ? C8 C7 C12 C11 0.1(7) . . . . ? O1 C7 C12 C11 -177.1(4) . . . . ? C8 C7 C12 C13 176.7(5) . . . . ? O1 C7 C12 C13 -0.5(6) . . . . ? C10 C11 C12 C7 -0.3(7) . . . . ? C10 C11 C12 C13 -177.0(5) . . . . ? C14 N1 C13 O2 2.9(7) . . . . ? P1 N1 C13 O2 -171.8(4) . . . . ? C14 N1 C13 C12 -177.4(4) . . . . ? P1 N1 C13 C12 7.9(6) . . . . ? C7 C12 C13 O2 -167.9(5) . . . . ? C11 C12 C13 O2 8.6(7) . . . . ? C7 C12 C13 N1 12.4(6) . . . . ? C11 C12 C13 N1 -171.1(4) . . . . ? C13 N1 C14 C15 -77.8(6) . . . . ? P1 N1 C14 C15 97.0(5) . . . . ? N1 C14 C15 Cl1 175.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.702 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 955822' ####################################################################### # # 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_msb056 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 Cl3 N O2 P Ru' _chemical_formula_weight 611.87 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' 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' Ru Ru -1.2594 0.8363 '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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.9131(2) _cell_length_b 12.7270(2) _cell_length_c 14.3212(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.0010(10) _cell_angle_gamma 90.00 _cell_volume 2526.23(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15311 _cell_measurement_theta_min 3.2675 _cell_measurement_theta_max 32.7990 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 1.025 _exptl_absorpt_correction_T_min 0.7623 _exptl_absorpt_correction_T_max 0.8532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18569 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4442 _reflns_number_gt 3841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0291P)^2^+0.2161P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4442 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0514 _refine_ls_wR_factor_gt 0.0505 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Ru1 Ru 0.717724(11) 0.067991(11) 0.786568(11) 0.01697(6) Uani 1 1 d . . . Cl1 Cl 0.62446(4) 0.20631(4) 0.70978(3) 0.02492(12) Uani 1 1 d . . . Cl2 Cl 0.85776(4) 0.17878(4) 0.78367(4) 0.02635(12) Uani 1 1 d . . . Cl3 Cl 1.12405(4) 0.00717(5) 0.76597(4) 0.04173(16) Uani 1 1 d . . . P1 P 0.75434(3) 0.00987(4) 0.64296(3) 0.01656(11) Uani 1 1 d . . . O1 O 0.67700(9) -0.07937(9) 0.60400(9) 0.0196(3) Uani 1 1 d . . . O2 O 0.95158(10) -0.15807(10) 0.54639(10) 0.0266(3) Uani 1 1 d . . . N1 N 0.86128(11) -0.05468(11) 0.63391(11) 0.0169(3) Uani 1 1 d . . . C1 C 0.94339(14) -0.05108(15) 0.70672(14) 0.0198(4) Uani 1 1 d . . . H1A H 0.9688 -0.1231 0.7180 0.024 Uiso 1 1 calc R . . H1B H 0.9205 -0.0250 0.7660 0.024 Uiso 1 1 calc R . . C2 C 1.02420(14) 0.01957(16) 0.67857(14) 0.0237(5) Uani 1 1 d . . . H2A H 1.0020 0.0935 0.6744 0.028 Uiso 1 1 calc R . . H2B H 1.0439 -0.0018 0.6166 0.028 Uiso 1 1 calc R . . C3 C 0.87328(14) -0.11979(14) 0.55830(13) 0.0193(4) Uani 1 1 d . . . C4 C 0.78574(14) -0.14701(14) 0.49591(13) 0.0192(4) Uani 1 1 d . . . C5 C 0.79723(15) -0.20097(15) 0.41222(13) 0.0240(4) Uani 1 1 d . . . H5 H 0.8599 -0.2098 0.3919 0.029 Uiso 1 1 calc R . . C6 C 0.71831(16) -0.24130(16) 0.35920(14) 0.0274(5) Uani 1 1 d . . . H6 H 0.7266 -0.2766 0.3020 0.033 Uiso 1 1 calc R . . C7 C 0.62713(16) -0.23032(16) 0.38929(14) 0.0291(5) Uani 1 1 d . . . H7 H 0.5731 -0.2597 0.3533 0.035 Uiso 1 1 calc R . . C8 C 0.61377(15) -0.17674(15) 0.47168(14) 0.0259(5) Uani 1 1 d . . . H8 H 0.5511 -0.1696 0.4925 0.031 Uiso 1 1 calc R . . C9 C 0.69319(14) -0.13389(14) 0.52287(13) 0.0195(4) Uani 1 1 d . . . C10 C 0.75028(14) 0.10126(15) 0.54528(13) 0.0196(4) Uani 1 1 d . . . C11 C 0.83283(15) 0.14740(16) 0.51636(14) 0.0259(5) Uani 1 1 d . . . H11 H 0.8944 0.1267 0.5443 0.031 Uiso 1 1 calc R . . C12 C 0.82610(16) 0.22359(17) 0.44688(16) 0.0337(5) Uani 1 1 d . . . H12 H 0.8830 0.2537 0.4262 0.040 Uiso 1 1 calc R . . C13 C 0.73671(17) 0.25571(17) 0.40778(15) 0.0316(5) Uani 1 1 d . . . H13 H 0.7322 0.3094 0.3615 0.038 Uiso 1 1 calc R . . C14 C 0.65429(16) 0.21036(16) 0.43552(14) 0.0286(5) Uani 1 1 d . . . H14 H 0.5929 0.2320 0.4078 0.034 Uiso 1 1 calc R . . C15 C 0.66061(15) 0.13298(16) 0.50399(14) 0.0256(5) Uani 1 1 d . . . H15 H 0.6035 0.1015 0.5228 0.031 Uiso 1 1 calc R . . C16 C 0.88275(16) -0.02505(19) 0.95427(16) 0.0342(5) Uani 1 1 d . . . H16A H 0.9109 -0.0869 0.9263 0.051 Uiso 1 1 calc R . . H16B H 0.8858 -0.0337 1.0225 0.051 Uiso 1 1 calc R . . H16C H 0.9190 0.0378 0.9391 0.051 Uiso 1 1 calc R . . C17 C 0.77943(15) -0.01344(16) 0.91588(13) 0.0233(4) Uani 1 1 d . . . C18 C 0.73291(16) -0.08738(15) 0.85500(14) 0.0249(5) Uani 1 1 d . . . H18 H 0.7670 -0.1481 0.8379 0.030 Uiso 1 1 calc R . . C19 C 0.63590(15) -0.07284(15) 0.81867(14) 0.0231(4) Uani 1 1 d . . . H19 H 0.6063 -0.1240 0.7772 0.028 Uiso 1 1 calc R . . C20 C 0.58243(14) 0.01526(14) 0.84234(13) 0.0200(4) Uani 1 1 d . . . C21 C 0.62922(15) 0.08866(15) 0.90780(13) 0.0218(4) Uani 1 1 d . . . H21 H 0.5942 0.1476 0.9274 0.026 Uiso 1 1 calc R . . C22 C 0.72430(15) 0.07515(15) 0.94282(14) 0.0231(4) Uani 1 1 d . . . H22 H 0.7536 0.1254 0.9854 0.028 Uiso 1 1 calc R . . C23 C 0.47870(15) 0.03422(16) 0.80530(15) 0.0267(5) Uani 1 1 d . . . H23 H 0.4704 0.1114 0.7940 0.032 Uiso 1 1 calc R . . C24 C 0.44968(18) -0.02223(19) 0.71373(16) 0.0390(6) Uani 1 1 d . . . H24A H 0.4942 -0.0030 0.6671 0.058 Uiso 1 1 calc R . . H24B H 0.3839 -0.0018 0.6909 0.058 Uiso 1 1 calc R . . H24C H 0.4523 -0.0983 0.7241 0.058 Uiso 1 1 calc R . . C25 C 0.41310(16) 0.0024(2) 0.88120(17) 0.0384(6) Uani 1 1 d . . . H25A H 0.4202 -0.0730 0.8939 0.058 Uiso 1 1 calc R . . H25B H 0.3458 0.0179 0.8595 0.058 Uiso 1 1 calc R . . H25C H 0.4314 0.0420 0.9387 0.058 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 Ru1 0.01976(10) 0.01313(9) 0.01875(9) -0.00066(6) 0.00584(6) -0.00055(6) Cl1 0.0255(3) 0.0175(2) 0.0330(3) 0.0050(2) 0.0093(2) 0.0039(2) Cl2 0.0262(3) 0.0186(2) 0.0346(3) -0.0003(2) 0.0050(2) -0.0059(2) Cl3 0.0290(3) 0.0497(4) 0.0437(4) 0.0089(3) -0.0127(3) -0.0117(3) P1 0.0160(3) 0.0152(2) 0.0190(3) 0.0009(2) 0.00460(19) 0.0003(2) O1 0.0176(7) 0.0188(7) 0.0231(7) -0.0030(6) 0.0049(6) -0.0016(5) O2 0.0183(8) 0.0286(8) 0.0337(8) -0.0065(6) 0.0076(6) 0.0022(6) N1 0.0151(8) 0.0162(8) 0.0199(8) 0.0002(7) 0.0034(6) 0.0001(6) C1 0.0185(10) 0.0199(10) 0.0208(10) 0.0037(8) 0.0008(8) 0.0006(8) C2 0.0200(11) 0.0281(11) 0.0225(11) 0.0040(9) -0.0015(8) -0.0042(9) C3 0.0209(11) 0.0167(9) 0.0210(11) 0.0024(8) 0.0060(8) -0.0030(8) C4 0.0223(11) 0.0137(9) 0.0219(10) 0.0018(8) 0.0042(8) -0.0009(8) C5 0.0300(12) 0.0221(10) 0.0210(11) 0.0021(9) 0.0088(9) 0.0005(9) C6 0.0386(13) 0.0253(11) 0.0181(11) -0.0019(9) 0.0007(9) -0.0016(10) C7 0.0311(13) 0.0278(11) 0.0266(12) -0.0014(9) -0.0084(9) -0.0009(9) C8 0.0215(11) 0.0260(11) 0.0294(12) -0.0007(9) -0.0012(9) 0.0011(9) C9 0.0239(11) 0.0155(10) 0.0193(10) 0.0020(8) 0.0028(8) 0.0020(8) C10 0.0216(11) 0.0182(9) 0.0197(10) 0.0005(8) 0.0047(8) 0.0027(8) C11 0.0220(11) 0.0258(11) 0.0303(12) 0.0073(9) 0.0050(9) 0.0042(9) C12 0.0311(13) 0.0313(12) 0.0406(14) 0.0144(10) 0.0134(10) 0.0034(10) C13 0.0435(14) 0.0281(11) 0.0238(12) 0.0096(9) 0.0068(10) 0.0099(10) C14 0.0294(12) 0.0298(11) 0.0256(11) 0.0020(9) -0.0024(9) 0.0080(9) C15 0.0230(11) 0.0263(11) 0.0277(12) 0.0022(9) 0.0026(9) 0.0006(9) C16 0.0308(13) 0.0435(13) 0.0281(12) 0.0079(10) 0.0021(10) 0.0052(10) C17 0.0270(12) 0.0261(11) 0.0176(11) 0.0068(9) 0.0059(8) 0.0014(9) C18 0.0351(13) 0.0145(10) 0.0268(11) 0.0055(8) 0.0134(9) 0.0023(9) C19 0.0320(12) 0.0173(10) 0.0212(10) 0.0014(8) 0.0094(9) -0.0077(9) C20 0.0246(11) 0.0168(10) 0.0195(11) 0.0025(8) 0.0079(8) -0.0045(8) C21 0.0271(11) 0.0199(10) 0.0198(10) -0.0016(8) 0.0110(8) -0.0006(8) C22 0.0306(12) 0.0235(10) 0.0160(10) -0.0021(8) 0.0061(8) -0.0041(9) C23 0.0250(12) 0.0276(11) 0.0280(12) 0.0032(9) 0.0055(9) -0.0033(9) C24 0.0333(14) 0.0484(15) 0.0341(14) -0.0034(11) -0.0037(10) -0.0039(11) C25 0.0257(13) 0.0479(15) 0.0430(15) 0.0065(12) 0.0108(10) -0.0039(11) _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 Ru1 C19 2.1934(19) . ? Ru1 C18 2.2088(19) . ? Ru1 C20 2.2122(19) . ? Ru1 C17 2.2279(19) . ? Ru1 C21 2.230(2) . ? Ru1 C22 2.2335(19) . ? Ru1 P1 2.2845(5) . ? Ru1 Cl1 2.3965(5) . ? Ru1 Cl2 2.4083(5) . ? Cl3 C2 1.7939(19) . ? P1 O1 1.6292(13) . ? P1 N1 1.7144(16) . ? P1 C10 1.8164(19) . ? O1 C9 1.388(2) . ? O2 C3 1.219(2) . ? N1 C3 1.385(2) . ? N1 C1 1.479(2) . ? C1 C2 1.521(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.487(3) . ? C4 C9 1.386(3) . ? C4 C5 1.402(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C10 C11 1.385(3) . ? C10 C15 1.393(3) . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.373(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.501(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.402(3) . ? C17 C22 1.435(3) . ? C18 C19 1.416(3) . ? C18 H18 0.9500 . ? C19 C20 1.403(3) . ? C19 H19 0.9500 . ? C20 C21 1.438(3) . ? C20 C23 1.513(3) . ? C21 C22 1.384(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.519(3) . ? C23 C25 1.533(3) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C19 Ru1 C18 37.52(8) . . ? C19 Ru1 C20 37.15(7) . . ? C18 Ru1 C20 67.65(7) . . ? C19 Ru1 C17 67.36(7) . . ? C18 Ru1 C17 36.84(8) . . ? C20 Ru1 C17 80.63(7) . . ? C19 Ru1 C21 66.50(7) . . ? C18 Ru1 C21 78.36(7) . . ? C20 Ru1 C21 37.78(7) . . ? C17 Ru1 C21 66.84(7) . . ? C19 Ru1 C22 78.47(7) . . ? C18 Ru1 C22 66.30(7) . . ? C20 Ru1 C22 67.20(7) . . ? C17 Ru1 C22 37.53(7) . . ? C21 Ru1 C22 36.13(7) . . ? C19 Ru1 P1 94.85(5) . . ? C18 Ru1 P1 95.12(5) . . ? C20 Ru1 P1 119.36(5) . . ? C17 Ru1 P1 119.85(5) . . ? C21 Ru1 P1 157.03(5) . . ? C22 Ru1 P1 157.26(5) . . ? C19 Ru1 Cl1 115.23(6) . . ? C18 Ru1 Cl1 152.65(6) . . ? C20 Ru1 Cl1 86.84(5) . . ? C17 Ru1 Cl1 151.30(5) . . ? C21 Ru1 Cl1 87.53(5) . . ? C22 Ru1 Cl1 113.77(5) . . ? P1 Ru1 Cl1 88.801(17) . . ? C19 Ru1 Cl2 156.56(6) . . ? C18 Ru1 Cl2 119.05(6) . . ? C20 Ru1 Cl2 154.02(5) . . ? C17 Ru1 Cl2 91.89(5) . . ? C21 Ru1 Cl2 116.54(5) . . ? C22 Ru1 Cl2 91.77(5) . . ? P1 Ru1 Cl2 85.978(18) . . ? Cl1 Ru1 Cl2 88.194(17) . . ? O1 P1 N1 101.05(7) . . ? O1 P1 C10 101.97(8) . . ? N1 P1 C10 102.56(8) . . ? O1 P1 Ru1 109.98(5) . . ? N1 P1 Ru1 119.10(6) . . ? C10 P1 Ru1 119.45(6) . . ? C9 O1 P1 118.98(12) . . ? C3 N1 C1 115.56(15) . . ? C3 N1 P1 120.69(13) . . ? C1 N1 P1 123.64(13) . . ? N1 C1 C2 112.01(15) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C1 C2 Cl3 107.96(13) . . ? C1 C2 H2A 110.1 . . ? Cl3 C2 H2A 110.1 . . ? C1 C2 H2B 110.1 . . ? Cl3 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? O2 C3 N1 121.24(17) . . ? O2 C3 C4 121.19(17) . . ? N1 C3 C4 117.44(17) . . ? C9 C4 C5 118.36(18) . . ? C9 C4 C3 122.44(17) . . ? C5 C4 C3 118.62(18) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.95(19) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 120.59(19) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 118.9(2) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C4 121.54(18) . . ? C8 C9 O1 117.39(18) . . ? C4 C9 O1 121.05(17) . . ? C11 C10 C15 119.05(18) . . ? C11 C10 P1 122.07(15) . . ? C15 C10 P1 118.62(15) . . ? C10 C11 C12 120.35(19) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.24(19) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.00(19) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C10 120.3(2) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 117.77(19) . . ? C18 C17 C16 122.49(19) . . ? C22 C17 C16 119.74(18) . . ? C18 C17 Ru1 70.84(11) . . ? C22 C17 Ru1 71.45(11) . . ? C16 C17 Ru1 129.62(15) . . ? C17 C18 C19 120.96(18) . . ? C17 C18 Ru1 72.32(11) . . ? C19 C18 Ru1 70.65(11) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? Ru1 C18 H18 130.1 . . ? C20 C19 C18 121.61(18) . . ? C20 C19 Ru1 72.15(11) . . ? C18 C19 Ru1 71.83(11) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? Ru1 C19 H19 129.3 . . ? C19 C20 C21 117.20(18) . . ? C19 C20 C23 123.53(18) . . ? C21 C20 C23 119.25(18) . . ? C19 C20 Ru1 70.70(11) . . ? C21 C20 Ru1 71.78(11) . . ? C23 C20 Ru1 129.85(13) . . ? C22 C21 C20 121.30(18) . . ? C22 C21 Ru1 72.08(12) . . ? C20 C21 Ru1 70.44(11) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? Ru1 C21 H21 131.0 . . ? C21 C22 C17 121.09(18) . . ? C21 C22 Ru1 71.79(11) . . ? C17 C22 Ru1 71.02(11) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? Ru1 C22 H22 130.4 . . ? C20 C23 C24 113.64(18) . . ? C20 C23 C25 108.54(17) . . ? C24 C23 C25 110.94(18) . . ? C20 C23 H23 107.8 . . ? C24 C23 H23 107.8 . . ? C25 C23 H23 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C19 Ru1 P1 O1 22.35(7) . . . . ? C18 Ru1 P1 O1 60.01(8) . . . . ? C20 Ru1 P1 O1 -7.18(8) . . . . ? C17 Ru1 P1 O1 88.98(8) . . . . ? C21 Ru1 P1 O1 -12.07(15) . . . . ? C22 Ru1 P1 O1 93.90(15) . . . . ? Cl1 Ru1 P1 O1 -92.87(5) . . . . ? Cl2 Ru1 P1 O1 178.86(5) . . . . ? C19 Ru1 P1 N1 -93.49(8) . . . . ? C18 Ru1 P1 N1 -55.82(8) . . . . ? C20 Ru1 P1 N1 -123.02(8) . . . . ? C17 Ru1 P1 N1 -26.85(9) . . . . ? C21 Ru1 P1 N1 -127.90(14) . . . . ? C22 Ru1 P1 N1 -21.94(16) . . . . ? Cl1 Ru1 P1 N1 151.29(6) . . . . ? Cl2 Ru1 P1 N1 63.02(6) . . . . ? C19 Ru1 P1 C10 139.65(9) . . . . ? C18 Ru1 P1 C10 177.31(9) . . . . ? C20 Ru1 P1 C10 110.12(9) . . . . ? C17 Ru1 P1 C10 -153.72(9) . . . . ? C21 Ru1 P1 C10 105.23(15) . . . . ? C22 Ru1 P1 C10 -148.81(15) . . . . ? Cl1 Ru1 P1 C10 24.43(7) . . . . ? Cl2 Ru1 P1 C10 -63.85(7) . . . . ? N1 P1 O1 C9 -45.59(14) . . . . ? C10 P1 O1 C9 59.95(14) . . . . ? Ru1 P1 O1 C9 -172.33(11) . . . . ? O1 P1 N1 C3 38.38(15) . . . . ? C10 P1 N1 C3 -66.70(15) . . . . ? Ru1 P1 N1 C3 158.85(12) . . . . ? O1 P1 N1 C1 -137.60(14) . . . . ? C10 P1 N1 C1 117.33(15) . . . . ? Ru1 P1 N1 C1 -17.13(16) . . . . ? C3 N1 C1 C2 79.2(2) . . . . ? P1 N1 C1 C2 -104.68(18) . . . . ? N1 C1 C2 Cl3 -174.14(13) . . . . ? C1 N1 C3 O2 -10.8(3) . . . . ? P1 N1 C3 O2 172.89(14) . . . . ? C1 N1 C3 C4 165.13(16) . . . . ? P1 N1 C3 C4 -11.2(2) . . . . ? O2 C3 C4 C9 158.69(18) . . . . ? N1 C3 C4 C9 -17.3(3) . . . . ? O2 C3 C4 C5 -12.4(3) . . . . ? N1 C3 C4 C5 171.61(17) . . . . ? C9 C4 C5 C6 -1.1(3) . . . . ? C3 C4 C5 C6 170.42(18) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? C5 C6 C7 C8 1.5(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C7 C8 C9 C4 -2.7(3) . . . . ? C7 C8 C9 O1 178.95(17) . . . . ? C5 C4 C9 C8 3.0(3) . . . . ? C3 C4 C9 C8 -168.09(17) . . . . ? C5 C4 C9 O1 -178.70(16) . . . . ? C3 C4 C9 O1 10.2(3) . . . . ? P1 O1 C9 C8 -155.43(14) . . . . ? P1 O1 C9 C4 26.2(2) . . . . ? O1 P1 C10 C11 -138.73(17) . . . . ? N1 P1 C10 C11 -34.38(19) . . . . ? Ru1 P1 C10 C11 99.89(17) . . . . ? O1 P1 C10 C15 47.24(17) . . . . ? N1 P1 C10 C15 151.60(15) . . . . ? Ru1 P1 C10 C15 -74.14(17) . . . . ? C15 C10 C11 C12 -0.4(3) . . . . ? P1 C10 C11 C12 -174.40(16) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? C11 C12 C13 C14 -1.9(3) . . . . ? C12 C13 C14 C15 0.9(3) . . . . ? C13 C14 C15 C10 0.3(3) . . . . ? C11 C10 C15 C14 -0.6(3) . . . . ? P1 C10 C15 C14 173.63(15) . . . . ? C19 Ru1 C17 C18 28.76(12) . . . . ? C20 Ru1 C17 C18 65.01(13) . . . . ? C21 Ru1 C17 C18 101.82(13) . . . . ? C22 Ru1 C17 C18 129.56(18) . . . . ? P1 Ru1 C17 C18 -53.56(13) . . . . ? Cl1 Ru1 C17 C18 130.30(12) . . . . ? Cl2 Ru1 C17 C18 -140.00(12) . . . . ? C19 Ru1 C17 C22 -100.79(13) . . . . ? C18 Ru1 C17 C22 -129.56(18) . . . . ? C20 Ru1 C17 C22 -64.55(12) . . . . ? C21 Ru1 C17 C22 -27.74(11) . . . . ? P1 Ru1 C17 C22 176.88(10) . . . . ? Cl1 Ru1 C17 C22 0.74(19) . . . . ? Cl2 Ru1 C17 C22 90.44(11) . . . . ? C19 Ru1 C17 C16 145.5(2) . . . . ? C18 Ru1 C17 C16 116.8(2) . . . . ? C20 Ru1 C17 C16 -178.2(2) . . . . ? C21 Ru1 C17 C16 -141.4(2) . . . . ? C22 Ru1 C17 C16 -113.7(2) . . . . ? P1 Ru1 C17 C16 63.2(2) . . . . ? Cl1 Ru1 C17 C16 -112.92(19) . . . . ? Cl2 Ru1 C17 C16 -23.23(19) . . . . ? C22 C17 C18 C19 2.3(3) . . . . ? C16 C17 C18 C19 -178.74(18) . . . . ? Ru1 C17 C18 C19 -53.36(17) . . . . ? C22 C17 C18 Ru1 55.69(16) . . . . ? C16 C17 C18 Ru1 -125.38(19) . . . . ? C19 Ru1 C18 C17 -133.17(18) . . . . ? C20 Ru1 C18 C17 -104.77(13) . . . . ? C21 Ru1 C18 C17 -66.75(12) . . . . ? C22 Ru1 C18 C17 -30.86(12) . . . . ? P1 Ru1 C18 C17 135.53(12) . . . . ? Cl1 Ru1 C18 C17 -127.14(13) . . . . ? Cl2 Ru1 C18 C17 47.29(13) . . . . ? C20 Ru1 C18 C19 28.40(11) . . . . ? C17 Ru1 C18 C19 133.17(18) . . . . ? C21 Ru1 C18 C19 66.42(12) . . . . ? C22 Ru1 C18 C19 102.31(13) . . . . ? P1 Ru1 C18 C19 -91.30(11) . . . . ? Cl1 Ru1 C18 C19 6.0(2) . . . . ? Cl2 Ru1 C18 C19 -179.54(10) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? Ru1 C18 C19 C20 -54.50(17) . . . . ? C17 C18 C19 Ru1 54.12(17) . . . . ? C18 Ru1 C19 C20 133.25(18) . . . . ? C17 Ru1 C19 C20 104.96(13) . . . . ? C21 Ru1 C19 C20 31.43(11) . . . . ? C22 Ru1 C19 C20 67.32(12) . . . . ? P1 Ru1 C19 C20 -134.65(11) . . . . ? Cl1 Ru1 C19 C20 -43.69(12) . . . . ? Cl2 Ru1 C19 C20 134.26(13) . . . . ? C20 Ru1 C19 C18 -133.25(18) . . . . ? C17 Ru1 C19 C18 -28.28(12) . . . . ? C21 Ru1 C19 C18 -101.82(13) . . . . ? C22 Ru1 C19 C18 -65.93(12) . . . . ? P1 Ru1 C19 C18 92.10(11) . . . . ? Cl1 Ru1 C19 C18 -176.94(10) . . . . ? Cl2 Ru1 C19 C18 1.0(2) . . . . ? C18 C19 C20 C21 -2.1(3) . . . . ? Ru1 C19 C20 C21 -56.46(15) . . . . ? C18 C19 C20 C23 179.97(18) . . . . ? Ru1 C19 C20 C23 125.61(18) . . . . ? C18 C19 C20 Ru1 54.36(17) . . . . ? C18 Ru1 C20 C19 -28.66(12) . . . . ? C17 Ru1 C20 C19 -64.65(12) . . . . ? C21 Ru1 C20 C19 -128.69(17) . . . . ? C22 Ru1 C20 C19 -101.29(13) . . . . ? P1 Ru1 C20 C19 54.42(12) . . . . ? Cl1 Ru1 C20 C19 141.26(11) . . . . ? Cl2 Ru1 C20 C19 -139.43(11) . . . . ? C19 Ru1 C20 C21 128.69(17) . . . . ? C18 Ru1 C20 C21 100.03(12) . . . . ? C17 Ru1 C20 C21 64.04(12) . . . . ? C22 Ru1 C20 C21 27.41(11) . . . . ? P1 Ru1 C20 C21 -176.89(9) . . . . ? Cl1 Ru1 C20 C21 -90.05(11) . . . . ? Cl2 Ru1 C20 C21 -10.74(19) . . . . ? C19 Ru1 C20 C23 -118.0(2) . . . . ? C18 Ru1 C20 C23 -146.69(19) . . . . ? C17 Ru1 C20 C23 177.32(18) . . . . ? C21 Ru1 C20 C23 113.3(2) . . . . ? C22 Ru1 C20 C23 140.68(19) . . . . ? P1 Ru1 C20 C23 -63.61(18) . . . . ? Cl1 Ru1 C20 C23 23.23(17) . . . . ? Cl2 Ru1 C20 C23 102.53(19) . . . . ? C19 C20 C21 C22 2.7(3) . . . . ? C23 C20 C21 C22 -179.32(18) . . . . ? Ru1 C20 C21 C22 -53.26(17) . . . . ? C19 C20 C21 Ru1 55.92(15) . . . . ? C23 C20 C21 Ru1 -126.07(17) . . . . ? C19 Ru1 C21 C22 103.05(13) . . . . ? C18 Ru1 C21 C22 65.56(12) . . . . ? C20 Ru1 C21 C22 133.97(17) . . . . ? C17 Ru1 C21 C22 28.74(11) . . . . ? P1 Ru1 C21 C22 140.93(12) . . . . ? Cl1 Ru1 C21 C22 -138.01(11) . . . . ? Cl2 Ru1 C21 C22 -51.26(12) . . . . ? C19 Ru1 C21 C20 -30.93(11) . . . . ? C18 Ru1 C21 C20 -68.42(12) . . . . ? C17 Ru1 C21 C20 -105.23(12) . . . . ? C22 Ru1 C21 C20 -133.97(17) . . . . ? P1 Ru1 C21 C20 7.0(2) . . . . ? Cl1 Ru1 C21 C20 88.02(10) . . . . ? Cl2 Ru1 C21 C20 174.76(9) . . . . ? C20 C21 C22 C17 -0.7(3) . . . . ? Ru1 C21 C22 C17 -53.26(17) . . . . ? C20 C21 C22 Ru1 52.52(17) . . . . ? C18 C17 C22 C21 -1.8(3) . . . . ? C16 C17 C22 C21 179.27(19) . . . . ? Ru1 C17 C22 C21 53.61(17) . . . . ? C18 C17 C22 Ru1 -55.39(16) . . . . ? C16 C17 C22 Ru1 125.65(18) . . . . ? C19 Ru1 C22 C21 -65.76(12) . . . . ? C18 Ru1 C22 C21 -103.15(13) . . . . ? C20 Ru1 C22 C21 -28.57(11) . . . . ? C17 Ru1 C22 C21 -133.47(17) . . . . ? P1 Ru1 C22 C21 -140.48(13) . . . . ? Cl1 Ru1 C22 C21 46.92(12) . . . . ? Cl2 Ru1 C22 C21 135.72(11) . . . . ? C19 Ru1 C22 C17 67.71(12) . . . . ? C18 Ru1 C22 C17 30.32(12) . . . . ? C20 Ru1 C22 C17 104.90(13) . . . . ? C21 Ru1 C22 C17 133.47(17) . . . . ? P1 Ru1 C22 C17 -7.0(2) . . . . ? Cl1 Ru1 C22 C17 -179.61(10) . . . . ? Cl2 Ru1 C22 C17 -90.81(11) . . . . ? C19 C20 C23 C24 -23.3(3) . . . . ? C21 C20 C23 C24 158.81(19) . . . . ? Ru1 C20 C23 C24 68.8(2) . . . . ? C19 C20 C23 C25 100.6(2) . . . . ? C21 C20 C23 C25 -77.3(2) . . . . ? Ru1 C20 C23 C25 -167.28(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.332 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 955823' ####################################################################### # # 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_msb057 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 Cl2 N2 O4 P Pd' _chemical_formula_weight 609.70 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' 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.9050(2) _cell_length_b 15.6580(2) _cell_length_c 17.4771(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.0960(10) _cell_angle_gamma 90.00 _cell_volume 4607.88(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13976 _cell_measurement_theta_min 3.4594 _cell_measurement_theta_max 32.6200 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2448 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_T_min 0.7041 _exptl_absorpt_correction_T_max 0.7953 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16661 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4060 _reflns_number_gt 3532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0358P)^2^+0.1109P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4060 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 Pd2 Pd 0.7500 -0.2500 0.5000 0.01766(8) Uani 1 2 d S . . Pd1 Pd 1.0000 0.017823(14) 0.2500 0.01363(8) Uani 1 2 d S . . Cl1 Cl 0.91234(3) 0.12356(3) 0.28663(3) 0.02103(13) Uani 1 1 d . . . Cl2 Cl 0.65672(3) 0.01540(4) 0.41656(3) 0.02699(15) Uani 1 1 d . . . P1 P 0.91380(3) -0.07690(3) 0.29023(3) 0.01505(13) Uani 1 1 d . . . O1 O 0.94606(9) -0.17263(9) 0.30761(8) 0.0178(3) Uani 1 1 d . . . O2 O 0.90257(10) -0.05375(11) 0.50664(9) 0.0252(4) Uani 1 1 d . . . O3 O 0.77581(10) -0.28827(11) 0.39712(9) 0.0264(4) Uani 1 1 d . . . O4 O 0.97744(9) -0.34137(10) 0.55619(9) 0.0257(4) Uani 1 1 d . . . N1 N 0.87853(10) -0.05582(12) 0.37649(10) 0.0161(4) Uani 1 1 d . . . N2 N 0.85958(11) -0.27681(12) 0.54400(10) 0.0197(4) Uani 1 1 d . . . C1 C 1.00094(13) -0.18216(14) 0.37190(13) 0.0182(5) Uani 1 1 d . . . C2 C 1.06189(15) -0.24003(14) 0.36748(14) 0.0237(5) Uani 1 1 d . . . H2 H 1.0665 -0.2726 0.3222 0.028 Uiso 1 1 calc R . . C3 C 1.11640(15) -0.24927(15) 0.43128(15) 0.0277(6) Uani 1 1 d . . . H3 H 1.1591 -0.2885 0.4294 0.033 Uiso 1 1 calc R . . C4 C 1.10958(15) -0.20231(15) 0.49758(14) 0.0268(6) Uani 1 1 d . . . H4 H 1.1481 -0.2085 0.5402 0.032 Uiso 1 1 calc R . . C5 C 1.04684(14) -0.14648(15) 0.50177(13) 0.0239(5) Uani 1 1 d . . . H5 H 1.0413 -0.1157 0.5478 0.029 Uiso 1 1 calc R . . C6 C 0.99123(13) -0.13525(14) 0.43788(13) 0.0192(5) Uani 1 1 d . . . C7 C 0.92211(14) -0.07811(14) 0.44500(13) 0.0194(5) Uani 1 1 d . . . C8 C 0.80788(13) -0.00063(14) 0.38242(13) 0.0189(5) Uani 1 1 d . . . H8A H 0.7916 0.0252 0.3318 0.023 Uiso 1 1 calc R . . H8B H 0.8213 0.0461 0.4194 0.023 Uiso 1 1 calc R . . C9 C 0.74025(13) -0.05310(15) 0.40886(14) 0.0218(5) Uani 1 1 d . . . H9A H 0.7565 -0.0795 0.4593 0.026 Uiso 1 1 calc R . . H9B H 0.7260 -0.0993 0.3715 0.026 Uiso 1 1 calc R . . C10 C 0.82856(13) -0.09446(14) 0.22431(12) 0.0179(5) Uani 1 1 d . . . C11 C 0.77479(13) -0.15993(14) 0.23796(13) 0.0212(5) Uani 1 1 d . . . H11 H 0.7832 -0.1949 0.2824 0.025 Uiso 1 1 calc R . . C12 C 0.70988(14) -0.17271(16) 0.18605(14) 0.0271(6) Uani 1 1 d . . . H12 H 0.6734 -0.2172 0.1946 0.033 Uiso 1 1 calc R . . C13 C 0.69699(15) -0.12145(16) 0.12142(14) 0.0277(6) Uani 1 1 d . . . H13 H 0.6513 -0.1301 0.0865 0.033 Uiso 1 1 calc R . . C14 C 0.75058(15) -0.05797(16) 0.10787(14) 0.0291(6) Uani 1 1 d . . . H14 H 0.7420 -0.0235 0.0631 0.035 Uiso 1 1 calc R . . C15 C 0.81673(14) -0.04406(15) 0.15896(13) 0.0221(5) Uani 1 1 d . . . H15 H 0.8536 -0.0004 0.1494 0.026 Uiso 1 1 calc R . . C16 C 0.83374(14) -0.34112(14) 0.38429(13) 0.0217(5) Uani 1 1 d . . . C17 C 0.83137(15) -0.37726(16) 0.30978(14) 0.0262(6) Uani 1 1 d . . . H17 H 0.7895 -0.3622 0.2724 0.031 Uiso 1 1 calc R . . C18 C 0.88869(16) -0.43382(17) 0.29065(14) 0.0307(6) Uani 1 1 d . . . H18 H 0.8857 -0.4573 0.2403 0.037 Uiso 1 1 calc R . . C19 C 0.95074(15) -0.45708(16) 0.34375(15) 0.0295(6) Uani 1 1 d . . . H19 H 0.9897 -0.4967 0.3302 0.035 Uiso 1 1 calc R . . C20 C 0.95542(14) -0.42248(15) 0.41596(14) 0.0252(5) Uani 1 1 d . . . H20 H 0.9980 -0.4384 0.4523 0.030 Uiso 1 1 calc R . . C21 C 0.89820(13) -0.36364(14) 0.43728(13) 0.0205(5) Uani 1 1 d . . . C22 C 0.90862(13) -0.32562(14) 0.51306(13) 0.0194(5) Uani 1 1 d . . . C23 C 0.89681(15) -0.24613(15) 0.61882(14) 0.0261(6) Uani 1 1 d . . . H23A H 0.8608 -0.2534 0.6600 0.031 Uiso 1 1 calc R . . H23B H 0.9125 -0.1854 0.6161 0.031 Uiso 1 1 calc R . . C24 C 0.96878(15) -0.30372(16) 0.63145(14) 0.0298(6) Uani 1 1 d . . . H24A H 1.0166 -0.2704 0.6495 0.036 Uiso 1 1 calc R . . H24B H 0.9601 -0.3486 0.6698 0.036 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 Pd2 0.01961(15) 0.01787(14) 0.01553(13) 0.00024(10) 0.00178(10) 0.00172(9) Pd1 0.01493(14) 0.01295(13) 0.01312(13) 0.000 0.00196(9) 0.000 Cl1 0.0237(3) 0.0167(3) 0.0236(3) 0.0008(2) 0.0069(2) 0.0041(2) Cl2 0.0184(3) 0.0383(4) 0.0246(3) 0.0026(3) 0.0041(2) 0.0058(2) P1 0.0159(3) 0.0152(3) 0.0142(3) 0.0008(2) 0.0023(2) -0.0002(2) O1 0.0201(9) 0.0157(8) 0.0175(8) 0.0004(7) 0.0010(6) 0.0011(6) O2 0.0300(10) 0.0294(9) 0.0165(8) -0.0012(8) 0.0030(7) 0.0029(7) O3 0.0281(10) 0.0331(10) 0.0176(8) -0.0022(8) 0.0007(7) 0.0124(8) O4 0.0192(9) 0.0297(9) 0.0274(9) -0.0023(8) -0.0021(7) 0.0010(7) N1 0.0149(10) 0.0181(10) 0.0157(9) 0.0018(8) 0.0030(8) 0.0011(7) N2 0.0221(11) 0.0199(10) 0.0170(9) -0.0005(8) 0.0001(8) -0.0013(8) C1 0.0189(13) 0.0157(11) 0.0202(12) 0.0063(10) 0.0030(9) -0.0032(9) C2 0.0254(14) 0.0184(12) 0.0280(13) 0.0034(10) 0.0060(11) 0.0015(9) C3 0.0231(14) 0.0215(12) 0.0387(15) 0.0121(12) 0.0037(12) 0.0069(10) C4 0.0235(14) 0.0252(13) 0.0306(13) 0.0091(12) -0.0042(11) -0.0010(10) C5 0.0277(14) 0.0226(13) 0.0207(12) 0.0050(10) -0.0014(10) -0.0047(10) C6 0.0209(13) 0.0165(11) 0.0200(11) 0.0056(10) 0.0001(10) -0.0028(9) C7 0.0224(13) 0.0167(12) 0.0191(12) 0.0026(10) 0.0024(10) -0.0035(9) C8 0.0184(12) 0.0182(11) 0.0206(12) 0.0000(10) 0.0047(10) 0.0038(9) C9 0.0184(13) 0.0208(12) 0.0270(12) -0.0009(11) 0.0059(10) 0.0016(9) C10 0.0178(12) 0.0191(12) 0.0170(11) -0.0015(10) 0.0019(9) 0.0011(9) C11 0.0234(13) 0.0214(12) 0.0193(11) 0.0005(10) 0.0040(10) -0.0017(9) C12 0.0261(14) 0.0265(13) 0.0288(13) -0.0063(11) 0.0026(11) -0.0089(10) C13 0.0242(14) 0.0333(14) 0.0240(13) -0.0070(11) -0.0072(11) -0.0019(11) C14 0.0371(16) 0.0264(13) 0.0219(13) 0.0026(11) -0.0072(11) 0.0016(11) C15 0.0238(13) 0.0207(12) 0.0214(12) -0.0004(10) -0.0002(10) -0.0039(10) C16 0.0241(13) 0.0196(12) 0.0220(12) 0.0033(10) 0.0057(10) -0.0002(10) C17 0.0305(15) 0.0289(14) 0.0194(12) 0.0007(11) 0.0029(10) 0.0013(10) C18 0.0415(17) 0.0305(14) 0.0216(13) -0.0046(11) 0.0114(12) 0.0020(12) C19 0.0291(15) 0.0288(14) 0.0320(14) -0.0048(12) 0.0111(12) 0.0054(11) C20 0.0215(14) 0.0265(13) 0.0277(13) 0.0045(11) 0.0042(10) -0.0012(10) C21 0.0210(13) 0.0193(12) 0.0216(12) 0.0012(10) 0.0052(10) -0.0034(9) C22 0.0178(13) 0.0181(11) 0.0227(12) 0.0050(10) 0.0032(10) -0.0028(9) C23 0.0278(15) 0.0294(14) 0.0206(12) -0.0055(11) -0.0010(11) 0.0000(10) C24 0.0298(15) 0.0324(14) 0.0257(13) -0.0071(12) -0.0068(11) 0.0014(11) _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 Pd2 O3 1.9803(15) 7_646 ? Pd2 O3 1.9803(15) . ? Pd2 N2 1.9864(18) 7_646 ? Pd2 N2 1.9864(18) . ? Pd1 P1 2.2359(6) . ? Pd1 P1 2.2359(6) 2_755 ? Pd1 Cl1 2.3484(5) . ? Pd1 Cl1 2.3484(5) 2_755 ? Cl2 C9 1.788(2) . ? P1 O1 1.6147(15) . ? P1 N1 1.7021(19) . ? P1 C10 1.784(2) . ? O1 C1 1.400(3) . ? O2 C7 1.216(3) . ? O3 C16 1.317(3) . ? O4 C22 1.352(3) . ? O4 C24 1.461(3) . ? N1 C7 1.393(3) . ? N1 C8 1.485(3) . ? N2 C22 1.282(3) . ? N2 C23 1.480(3) . ? C1 C2 1.379(3) . ? C1 C6 1.389(3) . ? C2 C3 1.390(4) . ? C2 H2 0.9500 . ? C3 C4 1.386(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.405(3) . ? C5 H5 0.9500 . ? C6 C7 1.486(3) . ? C8 C9 1.513(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.388(3) . ? C10 C11 1.405(3) . ? C11 C12 1.375(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.411(3) . ? C16 C17 1.417(3) . ? C17 C18 1.376(4) . ? C17 H17 0.9500 . ? C18 C19 1.386(4) . ? C18 H18 0.9500 . ? C19 C20 1.369(3) . ? C19 H19 0.9500 . ? C20 C21 1.410(3) . ? C20 H20 0.9500 . ? C21 C22 1.448(3) . ? C23 C24 1.515(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 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 O3 Pd2 O3 180.0 7_646 . ? O3 Pd2 N2 90.83(7) 7_646 7_646 ? O3 Pd2 N2 89.17(7) . 7_646 ? O3 Pd2 N2 89.17(7) 7_646 . ? O3 Pd2 N2 90.83(7) . . ? N2 Pd2 N2 180.00(10) 7_646 . ? P1 Pd1 P1 96.89(3) . 2_755 ? P1 Pd1 Cl1 86.40(2) . . ? P1 Pd1 Cl1 176.35(2) 2_755 . ? P1 Pd1 Cl1 176.35(2) . 2_755 ? P1 Pd1 Cl1 86.40(2) 2_755 2_755 ? Cl1 Pd1 Cl1 90.35(3) . 2_755 ? O1 P1 N1 98.76(8) . . ? O1 P1 C10 102.61(9) . . ? N1 P1 C10 105.98(10) . . ? O1 P1 Pd1 117.16(6) . . ? N1 P1 Pd1 116.06(7) . . ? C10 P1 Pd1 114.24(8) . . ? C1 O1 P1 116.01(13) . . ? C16 O3 Pd2 124.89(14) . . ? C22 O4 C24 106.17(17) . . ? C7 N1 C8 116.93(18) . . ? C7 N1 P1 120.83(15) . . ? C8 N1 P1 121.45(14) . . ? C22 N2 C23 109.02(19) . . ? C22 N2 Pd2 125.35(15) . . ? C23 N2 Pd2 125.60(15) . . ? C2 C1 C6 122.5(2) . . ? C2 C1 O1 118.0(2) . . ? C6 C1 O1 119.41(19) . . ? C1 C2 C3 118.0(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 118.3(2) . . ? C1 C6 C7 122.7(2) . . ? C5 C6 C7 119.0(2) . . ? O2 C7 N1 121.2(2) . . ? O2 C7 C6 122.7(2) . . ? N1 C7 C6 116.0(2) . . ? N1 C8 C9 109.85(18) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 Cl2 108.69(16) . . ? C8 C9 H9A 110.0 . . ? Cl2 C9 H9A 110.0 . . ? C8 C9 H9B 110.0 . . ? Cl2 C9 H9B 110.0 . . ? H9A C9 H9B 108.3 . . ? C15 C10 C11 120.4(2) . . ? C15 C10 P1 119.52(17) . . ? C11 C10 P1 120.03(17) . . ? C12 C11 C10 119.0(2) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.5(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 119.4(2) . . ? C14 C15 H15 120.3 . . ? C10 C15 H15 120.3 . . ? O3 C16 C21 126.0(2) . . ? O3 C16 C17 116.5(2) . . ? C21 C16 C17 117.4(2) . . ? C18 C17 C16 121.1(2) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 119.4(2) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 119.9(2) . . ? C20 C21 C22 118.7(2) . . ? C16 C21 C22 121.4(2) . . ? N2 C22 O4 115.5(2) . . ? N2 C22 C21 126.9(2) . . ? O4 C22 C21 117.6(2) . . ? N2 C23 C24 102.04(19) . . ? N2 C23 H23A 111.4 . . ? C24 C23 H23A 111.4 . . ? N2 C23 H23B 111.4 . . ? C24 C23 H23B 111.4 . . ? H23A C23 H23B 109.2 . . ? O4 C24 C23 104.62(18) . . ? O4 C24 H24A 110.8 . . ? C23 C24 H24A 110.8 . . ? O4 C24 H24B 110.8 . . ? C23 C24 H24B 110.8 . . ? H24A C24 H24B 108.9 . . ? 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 P1 Pd1 P1 O1 20.02(6) 2_755 . . . ? Cl1 Pd1 P1 O1 -161.57(7) . . . . ? Cl1 Pd1 P1 O1 -134.3(3) 2_755 . . . ? P1 Pd1 P1 N1 136.21(7) 2_755 . . . ? Cl1 Pd1 P1 N1 -45.38(7) . . . . ? Cl1 Pd1 P1 N1 -18.1(3) 2_755 . . . ? P1 Pd1 P1 C10 -99.99(8) 2_755 . . . ? Cl1 Pd1 P1 C10 78.43(8) . . . . ? Cl1 Pd1 P1 C10 105.7(3) 2_755 . . . ? N1 P1 O1 C1 -55.92(16) . . . . ? C10 P1 O1 C1 -164.59(15) . . . . ? Pd1 P1 O1 C1 69.43(15) . . . . ? O3 Pd2 O3 C16 110(100) 7_646 . . . ? N2 Pd2 O3 C16 -157.45(19) 7_646 . . . ? N2 Pd2 O3 C16 22.55(19) . . . . ? O1 P1 N1 C7 43.44(18) . . . . ? C10 P1 N1 C7 149.33(17) . . . . ? Pd1 P1 N1 C7 -82.68(17) . . . . ? O1 P1 N1 C8 -147.07(16) . . . . ? C10 P1 N1 C8 -41.17(19) . . . . ? Pd1 P1 N1 C8 86.81(16) . . . . ? O3 Pd2 N2 C22 161.8(2) 7_646 . . . ? O3 Pd2 N2 C22 -18.2(2) . . . . ? N2 Pd2 N2 C22 -31(100) 7_646 . . . ? O3 Pd2 N2 C23 -16.06(18) 7_646 . . . ? O3 Pd2 N2 C23 163.94(18) . . . . ? N2 Pd2 N2 C23 152(100) 7_646 . . . ? P1 O1 C1 C2 -143.13(17) . . . . ? P1 O1 C1 C6 38.5(3) . . . . ? C6 C1 C2 C3 -1.8(3) . . . . ? O1 C1 C2 C3 179.9(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? O1 C1 C6 C5 179.55(19) . . . . ? C2 C1 C6 C7 -175.0(2) . . . . ? O1 C1 C6 C7 3.4(3) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C8 N1 C7 O2 0.5(3) . . . . ? P1 N1 C7 O2 170.42(18) . . . . ? C8 N1 C7 C6 178.39(18) . . . . ? P1 N1 C7 C6 -11.7(3) . . . . ? C1 C6 C7 O2 161.3(2) . . . . ? C5 C6 C7 O2 -14.8(3) . . . . ? C1 C6 C7 N1 -16.5(3) . . . . ? C5 C6 C7 N1 167.3(2) . . . . ? C7 N1 C8 C9 -76.5(2) . . . . ? P1 N1 C8 C9 113.64(19) . . . . ? N1 C8 C9 Cl2 179.27(15) . . . . ? O1 P1 C10 C15 -134.64(18) . . . . ? N1 P1 C10 C15 122.27(19) . . . . ? Pd1 P1 C10 C15 -6.8(2) . . . . ? O1 P1 C10 C11 44.2(2) . . . . ? N1 P1 C10 C11 -58.9(2) . . . . ? Pd1 P1 C10 C11 172.02(16) . . . . ? C15 C10 C11 C12 -0.7(3) . . . . ? P1 C10 C11 C12 -179.48(18) . . . . ? C10 C11 C12 C13 -0.6(4) . . . . ? C11 C12 C13 C14 1.4(4) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C13 C14 C15 C10 -0.3(4) . . . . ? C11 C10 C15 C14 1.1(3) . . . . ? P1 C10 C15 C14 179.89(19) . . . . ? Pd2 O3 C16 C21 -16.1(3) . . . . ? Pd2 O3 C16 C17 165.07(16) . . . . ? O3 C16 C17 C18 -179.4(2) . . . . ? C21 C16 C17 C18 1.7(4) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C17 C18 C19 C20 -0.7(4) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C19 C20 C21 C16 1.5(4) . . . . ? C19 C20 C21 C22 -176.7(2) . . . . ? O3 C16 C21 C20 178.9(2) . . . . ? C17 C16 C21 C20 -2.3(3) . . . . ? O3 C16 C21 C22 -3.0(4) . . . . ? C17 C16 C21 C22 175.8(2) . . . . ? C23 N2 C22 O4 4.0(3) . . . . ? Pd2 N2 C22 O4 -174.10(14) . . . . ? C23 N2 C22 C21 -174.9(2) . . . . ? Pd2 N2 C22 C21 7.0(3) . . . . ? C24 O4 C22 N2 6.9(3) . . . . ? C24 O4 C22 C21 -174.1(2) . . . . ? C20 C21 C22 N2 -173.8(2) . . . . ? C16 C21 C22 N2 8.0(4) . . . . ? C20 C21 C22 O4 7.3(3) . . . . ? C16 C21 C22 O4 -170.9(2) . . . . ? C22 N2 C23 C24 -12.5(3) . . . . ? Pd2 N2 C23 C24 165.58(16) . . . . ? C22 O4 C24 C23 -14.3(2) . . . . ? N2 C23 C24 O4 15.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.374 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 955824' ####################################################################### # # 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_bc02b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H26 Cl4 N2 O4 P2 Pd' _chemical_formula_sum 'C30 H26 Cl4 N2 O4 P2 Pd' _chemical_formula_weight 788.67 loop_ _vrf_RINTA01 Type_3_C ; PROBLEM: The value of Rint is greater than 0.12, Rint given 0.140 RESPONSE: The quality of the data was poor due crystal quality. ; 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' 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 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.875(8) _cell_length_b 12.995(6) _cell_length_c 17.358(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.2900(10) _cell_angle_gamma 90.00 _cell_volume 3058(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2453 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 25.30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.190 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.713 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 1.102 _exptl_absorpt_process_details 'NUMABS (Rigaku, 1999)' _exptl_absorpt_correction_T_min 0.660 _exptl_absorpt_correction_T_max 0.811 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.111 _diffrn_standards_interval_count - _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11351 _diffrn_reflns_av_R_equivalents 0.1396 _diffrn_reflns_av_sigmaI/netI 0.0802 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2765 _reflns_number_gt 2343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)' _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b23' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b23' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_publication_material 'CrystalStructure 4.0' _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^)+(0.0423P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2765 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.0000 0.23024(2) 0.2500 0.01064(13) Uani 1 2 d S . . Cl1 Cl 0.01170(5) 0.10406(5) 0.15896(4) 0.01661(18) Uani 1 1 d . . . Cl2 Cl -0.09355(6) 0.23089(5) 0.59906(5) 0.0270(2) Uani 1 1 d . . . P1 P -0.02432(5) 0.34370(5) 0.33619(4) 0.01188(18) Uani 1 1 d . . . O1 O 0.01578(14) 0.45954(13) 0.33688(11) 0.0141(4) Uani 1 1 d . . . O2 O 0.17291(15) 0.31744(16) 0.56100(11) 0.0219(5) Uani 1 1 d . . . N1 N 0.02914(17) 0.32107(17) 0.44222(12) 0.0141(5) Uani 1 1 d . . . C1 C 0.1284(2) 0.3463(2) 0.48776(16) 0.0158(6) Uani 1 1 d . . . C2 C 0.1744(2) 0.4123(2) 0.44456(16) 0.0151(6) Uani 1 1 d . . . C3 C 0.2772(2) 0.4246(2) 0.47957(17) 0.0192(6) Uani 1 1 d . . . H3 H 0.3173 0.3867 0.5284 0.023 Uiso 1 1 calc R . . C4 C 0.3199(2) 0.4920(2) 0.44295(18) 0.0238(7) Uani 1 1 d . . . H4 H 0.3896 0.4994 0.4664 0.029 Uiso 1 1 calc R . . C5 C 0.2623(2) 0.5489(2) 0.37249(17) 0.0216(6) Uani 1 1 d . . . H5 H 0.2926 0.5956 0.3483 0.026 Uiso 1 1 calc R . . C6 C 0.1608(2) 0.5381(2) 0.33715(16) 0.0183(6) Uani 1 1 d . . . H6 H 0.1209 0.5774 0.2891 0.022 Uiso 1 1 calc R . . C7 C 0.1188(2) 0.4696(2) 0.37269(15) 0.0142(6) Uani 1 1 d . . . C8 C -0.15221(19) 0.3628(2) 0.31060(15) 0.0146(6) Uani 1 1 d . . . C9 C -0.1827(2) 0.4445(2) 0.34691(16) 0.0176(6) Uani 1 1 d . . . H9 H -0.1354 0.4875 0.3879 0.021 Uiso 1 1 calc R . . C10 C -0.2829(2) 0.4618(2) 0.32228(17) 0.0204(6) Uani 1 1 d . . . H10 H -0.3047 0.5173 0.3459 0.024 Uiso 1 1 calc R . . C11 C -0.3507(2) 0.3977(2) 0.26310(16) 0.0198(6) Uani 1 1 d . . . H11 H -0.4192 0.4092 0.2468 0.024 Uiso 1 1 calc R . . C12 C -0.3207(2) 0.3172(2) 0.22726(16) 0.0203(6) Uani 1 1 d . . . H12 H -0.3683 0.2738 0.1869 0.024 Uiso 1 1 calc R . . C13 C -0.2207(2) 0.2998(2) 0.25020(16) 0.0168(6) Uani 1 1 d . . . H13 H -0.1995 0.2456 0.2249 0.020 Uiso 1 1 calc R . . C14 C -0.0173(2) 0.2550(2) 0.48471(17) 0.0174(6) Uani 1 1 d . . . H14A H 0.0299 0.2010 0.5174 0.021 Uiso 1 1 calc R . . H14B H -0.0759 0.2208 0.4417 0.021 Uiso 1 1 calc R . . C15 C -0.0478(2) 0.3179(2) 0.54356(17) 0.0205(6) Uani 1 1 d . . . H15A H -0.0998 0.3678 0.5107 0.025 Uiso 1 1 calc R . . H15B H 0.0094 0.3566 0.5841 0.025 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 0.0088(2) 0.00818(19) 0.01364(19) 0.000 0.00331(14) 0.000 Cl1 0.0197(4) 0.0108(3) 0.0192(3) -0.0007(2) 0.0078(3) 0.0027(3) Cl2 0.0346(5) 0.0233(4) 0.0324(4) 0.0054(3) 0.0231(4) 0.0008(3) P1 0.0109(4) 0.0092(3) 0.0144(4) -0.0004(2) 0.0042(3) -0.0004(3) O1 0.0132(10) 0.0106(9) 0.0167(9) -0.0016(7) 0.0044(8) -0.0011(8) O2 0.0218(11) 0.0194(11) 0.0195(10) 0.0017(8) 0.0035(9) -0.0019(10) N1 0.0153(12) 0.0109(11) 0.0153(11) -0.0002(9) 0.0053(10) -0.0016(10) C1 0.0157(15) 0.0103(13) 0.0185(14) -0.0042(10) 0.0040(12) 0.0010(12) C2 0.0138(14) 0.0116(13) 0.0172(13) -0.0055(10) 0.0037(12) -0.0016(12) C3 0.0157(15) 0.0171(14) 0.0216(14) -0.0059(11) 0.0043(12) -0.0016(13) C4 0.0156(15) 0.0231(16) 0.0324(17) -0.0086(12) 0.0095(14) -0.0051(14) C5 0.0220(16) 0.0183(14) 0.0271(15) -0.0060(12) 0.0128(14) -0.0091(14) C6 0.0222(16) 0.0120(13) 0.0191(14) -0.0023(11) 0.0070(13) -0.0008(13) C7 0.0131(14) 0.0089(12) 0.0198(14) -0.0057(10) 0.0060(12) -0.0013(11) C8 0.0108(14) 0.0137(13) 0.0188(13) 0.0032(11) 0.0056(11) 0.0007(12) C9 0.0189(15) 0.0132(13) 0.0202(13) -0.0003(10) 0.0074(12) 0.0003(12) C10 0.0239(16) 0.0162(14) 0.0256(15) 0.0053(11) 0.0149(13) 0.0066(14) C11 0.0123(14) 0.0218(15) 0.0244(14) 0.0111(12) 0.0066(12) 0.0032(13) C12 0.0168(16) 0.0193(15) 0.0233(15) 0.0020(12) 0.0067(13) -0.0022(13) C13 0.0162(15) 0.0129(13) 0.0211(14) 0.0007(11) 0.0075(12) 0.0007(13) C14 0.0191(16) 0.0130(12) 0.0187(14) 0.0007(11) 0.0063(13) 0.0001(13) C15 0.0278(17) 0.0138(13) 0.0253(15) 0.0013(11) 0.0165(14) -0.0009(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 P1 2.2334(9) . ? Pd1 P1 2.2334(9) 2 ? Pd1 Cl1 2.3329(10) . ? Pd1 Cl1 2.3329(10) 2 ? Cl2 C15 1.791(3) . ? P1 O1 1.617(2) . ? P1 N1 1.704(2) . ? P1 C8 1.784(3) . ? O1 C7 1.403(3) . ? O2 C1 1.226(3) . ? N1 C1 1.397(4) . ? N1 C14 1.475(3) . ? C1 C2 1.480(4) . ? C2 C7 1.395(4) . ? C2 C3 1.402(4) . ? C3 C4 1.381(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 C7 1.371(4) . ? C6 H6 0.9500 . ? C8 C13 1.388(4) . ? C8 C9 1.402(4) . ? C9 C10 1.389(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C10 H10 0.9500 . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C12 C13 1.391(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.517(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 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 P1 Pd1 P1 97.38(5) . 2 ? P1 Pd1 Cl1 174.57(2) . . ? P1 Pd1 Cl1 86.13(4) 2 . ? P1 Pd1 Cl1 86.13(4) . 2 ? P1 Pd1 Cl1 174.57(2) 2 2 ? Cl1 Pd1 Cl1 90.69(5) . 2 ? O1 P1 N1 98.39(10) . . ? O1 P1 C8 102.97(12) . . ? N1 P1 C8 105.61(11) . . ? O1 P1 Pd1 117.29(7) . . ? N1 P1 Pd1 118.52(9) . . ? C8 P1 Pd1 112.03(9) . . ? C7 O1 P1 114.97(16) . . ? C1 N1 C14 117.2(2) . . ? C1 N1 P1 119.07(18) . . ? C14 N1 P1 122.29(19) . . ? O2 C1 N1 120.6(2) . . ? O2 C1 C2 122.5(3) . . ? N1 C1 C2 116.8(2) . . ? C7 C2 C3 117.8(3) . . ? C7 C2 C1 122.3(3) . . ? C3 C2 C1 119.7(2) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 122.4(3) . . ? C6 C7 O1 118.6(2) . . ? C2 C7 O1 119.0(2) . . ? C13 C8 C9 120.9(3) . . ? C13 C8 P1 118.8(2) . . ? C9 C8 P1 120.2(2) . . ? C10 C9 C8 119.3(3) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 121.2(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.0(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C8 C13 C12 119.1(3) . . ? C8 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? N1 C14 C15 110.8(2) . . ? N1 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C14 C15 Cl2 107.9(2) . . ? C14 C15 H15A 110.1 . . ? Cl2 C15 H15A 110.1 . . ? C14 C15 H15B 110.1 . . ? Cl2 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.062 _refine_diff_density_min -1.256 _refine_diff_density_rms 0.138 _database_code_depnum_ccdc_archive 'CCDC 955825'