# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Narcis Avarvari' _publ_contact_author_address ; UMR 6200 Chemistry CNRS-Université d'Angers UFR Sciences 2 Bd. Lavoisier, Angers 49045 FRANCE ; _publ_contact_author_email NARCIS.AVARVARI@UNIV-ANGERS.FR _publ_section_title ; Tetrathiafulvalene based phosphino-oxazolines: a new family of redox active chiral ligands ; loop_ _publ_author_name 'Narcis Avarvari' 'Marc Fourmigue' 'Celine Rethore' data_EDT-TTF-OX,_2b _database_code_depnum_ccdc_archive 'CCDC 232992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N O S6' _chemical_formula_weight 377.58 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3686(10) _cell_length_b 7.667(2) _cell_length_c 16.419(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.60(2) _cell_angle_gamma 90.00 _cell_volume 790.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1542 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 21.65 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.858 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.9556 _exptl_absorpt_correction_T_max 0.9703 _exptl_absorpt_process_details faceit _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type STOE-IPDS _diffrn_measurement_method 'Oscillation, Phi. incr. = 1.4' _diffrn_detector_area_resol_mean 6.6 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6434 _diffrn_reflns_av_R_equivalents 0.1537 _diffrn_reflns_av_sigmaI/netI 0.3049 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.87 _reflns_number_total 2865 _reflns_number_gt 682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE [STOE-IPDS]' _computing_cell_refinement 'SELECT, CELL [STOE-IPDS]' _computing_data_reduction 'INTEGRATE [STOE-IPDS]' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(5) _refine_ls_number_reflns 2865 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2526 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.2504 _refine_ls_wR_factor_gt 0.1848 _refine_ls_goodness_of_fit_ref 0.755 _refine_ls_restrained_S_all 0.755 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S5 S 1.0691(9) 0.8973(9) 0.8658(3) 0.1035(19) Uani 1 1 d . . . S6 S 0.5973(11) 0.9220(11) 0.9461(4) 0.147(3) Uani 1 1 d . . . S3 S 0.8881(9) 0.5790(7) 0.7878(3) 0.0901(17) Uani 1 1 d . . . S4 S 0.4764(8) 0.6069(8) 0.8466(3) 0.0911(17) Uani 1 1 d . . . S1 S 0.7473(9) 0.2206(7) 0.6972(3) 0.0826(15) Uani 1 1 d . . . S2 S 0.3283(9) 0.2379(9) 0.7531(3) 0.0997(19) Uani 1 1 d . . . C7 C 0.988(5) 1.049(4) 0.926(2) 0.198(16) Uani 1 1 d . . . H7A H 1.1058 1.0677 0.9705 0.237 Uiso 1 1 calc R . . H7B H 0.9736 1.1554 0.8933 0.237 Uiso 1 1 calc R . . C8 C 0.811(5) 1.038(4) 0.961(2) 0.23(2) Uani 1 1 d . . . H8A H 0.7581 1.1568 0.9580 0.275 Uiso 1 1 calc R . . H8B H 0.8680 1.0187 1.0189 0.275 Uiso 1 1 calc R . . C5 C 0.853(3) 0.753(3) 0.8474(10) 0.079(6) Uani 1 1 d . . . C6 C 0.667(3) 0.765(2) 0.8792(10) 0.074(5) Uani 1 1 d . . . C4 C 0.643(3) 0.488(3) 0.7926(12) 0.075(5) Uani 1 1 d . . . C3 C 0.588(3) 0.345(4) 0.7549(11) 0.080(6) Uani 1 1 d . . . C1 C 0.568(4) 0.047(2) 0.6776(11) 0.086(7) Uani 1 1 d . . . C2 C 0.383(4) 0.055(4) 0.7062(13) 0.134(11) Uani 1 1 d . . . H2 H 0.2879 -0.0379 0.7000 0.161 Uiso 1 1 calc R . . C9 C 0.669(4) -0.093(2) 0.6320(10) 0.083(7) Uani 1 1 d . . . C10 C 0.621(4) -0.334(3) 0.5574(14) 0.109(7) Uani 1 1 d . . . H10A H 0.5508 -0.3272 0.5004 0.131 Uiso 1 1 calc R . . H10B H 0.6199 -0.4550 0.5752 0.131 Uiso 1 1 calc R . . C11 C 0.847(4) -0.269(3) 0.5655(12) 0.097(7) Uani 1 1 d . . . H11 H 0.9441 -0.3542 0.5964 0.117 Uiso 1 1 calc R . . C12 C 0.917(4) -0.233(3) 0.4840(10) 0.106(8) Uani 1 1 d . . . H12A H 1.0602 -0.1895 0.4934 0.159 Uiso 1 1 calc R . . H12B H 0.8241 -0.1471 0.4542 0.159 Uiso 1 1 calc R . . H12C H 0.9101 -0.3384 0.4524 0.159 Uiso 1 1 calc R . . O1 O 0.517(3) -0.227(2) 0.6082(8) 0.112(6) Uani 1 1 d . . . N1 N 0.845(3) -0.109(3) 0.6156(11) 0.101(6) 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 S5 0.081(5) 0.124(5) 0.108(4) -0.025(4) 0.020(3) -0.025(4) S6 0.079(5) 0.212(8) 0.157(6) -0.122(6) 0.041(4) -0.034(5) S3 0.067(4) 0.117(5) 0.092(4) -0.019(3) 0.030(3) -0.017(4) S4 0.061(4) 0.130(5) 0.088(3) -0.019(3) 0.028(3) -0.018(3) S1 0.066(4) 0.093(4) 0.093(3) -0.001(3) 0.023(3) -0.010(3) S2 0.068(4) 0.133(5) 0.102(4) -0.020(4) 0.025(3) -0.028(4) C7 0.08(2) 0.15(3) 0.37(5) -0.14(3) 0.07(3) -0.038(19) C8 0.12(3) 0.24(4) 0.35(5) -0.19(4) 0.10(3) -0.07(3) C5 0.077(16) 0.089(15) 0.069(11) 0.031(11) 0.003(10) 0.007(12) C6 0.080(16) 0.077(14) 0.058(10) 0.001(10) -0.003(9) 0.000(11) C4 0.069(15) 0.092(14) 0.068(11) 0.022(11) 0.028(10) -0.004(12) C3 0.050(13) 0.134(19) 0.057(10) 0.004(12) 0.008(9) -0.028(12) C1 0.13(2) 0.067(14) 0.064(12) -0.024(10) 0.017(12) -0.014(13) C2 0.11(2) 0.21(3) 0.094(16) -0.055(19) 0.047(16) -0.03(2) C9 0.13(2) 0.039(11) 0.067(11) -0.005(10) -0.033(13) -0.034(14) C10 0.12(2) 0.095(18) 0.111(17) 0.002(13) 0.014(16) -0.013(15) C11 0.13(2) 0.058(13) 0.099(15) 0.010(13) 0.007(13) 0.027(15) C12 0.16(2) 0.102(17) 0.059(12) -0.021(11) 0.019(12) -0.005(14) O1 0.129(16) 0.121(13) 0.099(10) -0.005(9) 0.053(10) 0.004(11) N1 0.068(14) 0.131(18) 0.107(13) 0.010(13) 0.025(10) 0.000(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 S5 C7 1.66(3) . ? S5 C5 1.75(2) . ? S6 C8 1.61(3) . ? S6 C6 1.74(2) . ? S3 C5 1.69(2) . ? S3 C4 1.72(2) . ? S4 C6 1.73(2) . ? S4 C4 1.75(2) . ? S1 C1 1.75(2) . ? S1 C3 1.77(2) . ? S2 C2 1.66(3) . ? S2 C3 1.84(2) . ? C7 C8 1.35(4) . ? C5 C6 1.38(2) . ? C4 C3 1.28(2) . ? C1 C2 1.34(3) . ? C1 C9 1.51(3) . ? C9 N1 1.20(3) . ? C9 O1 1.42(2) . ? C10 O1 1.41(3) . ? C10 C11 1.51(3) . ? C11 N1 1.48(3) . ? C11 C12 1.50(2) . ? 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 C7 S5 C5 103.4(13) . . ? C8 S6 C6 100.4(13) . . ? C5 S3 C4 94.8(11) . . ? C6 S4 C4 93.9(11) . . ? C1 S1 C3 95.3(11) . . ? C2 S2 C3 97.2(13) . . ? C8 C7 S5 125(2) . . ? C7 C8 S6 135(2) . . ? C6 C5 S3 118.5(15) . . ? C6 C5 S5 126.5(16) . . ? S3 C5 S5 115.0(13) . . ? C5 C6 S4 116.1(14) . . ? C5 C6 S6 127.7(16) . . ? S4 C6 S6 116.2(13) . . ? C3 C4 S3 120.0(15) . . ? C3 C4 S4 123.5(16) . . ? S3 C4 S4 116.4(15) . . ? C4 C3 S1 125.8(14) . . ? C4 C3 S2 124.0(16) . . ? S1 C3 S2 110.2(14) . . ? C2 C1 C9 133(2) . . ? C2 C1 S1 119.0(18) . . ? C9 C1 S1 108.1(17) . . ? C1 C2 S2 118(2) . . ? N1 C9 O1 119(2) . . ? N1 C9 C1 133(2) . . ? O1 C9 C1 109(2) . . ? O1 C10 C11 106.8(18) . . ? N1 C11 C12 112.0(19) . . ? N1 C11 C10 103.1(17) . . ? C12 C11 C10 114(2) . . ? C10 O1 C9 102.6(18) . . ? C9 N1 C11 108(2) . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.87 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.355 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.061 #===END data_(EDT-TTF-PHOX)PdCl2,_4 _database_code_depnum_ccdc_archive 'CCDC 232993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Cl4 N O2 P Pd S6' _chemical_formula_weight 841.98 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' Cl Cl 0.1484 0.1585 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3583(3) _cell_length_b 12.6818(4) _cell_length_c 12.9393(2) _cell_angle_alpha 69.912(2) _cell_angle_beta 85.895(2) _cell_angle_gamma 70.706(2) _cell_volume 1650.28(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 158 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 1.340 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6722 _exptl_absorpt_correction_T_max 0.7328 _exptl_absorpt_process_details multiscan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31866 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 11.60 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7309 _reflns_number_gt 5499 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg&Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+2.6590P] 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 7309 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 Pd Pd 0.48843(2) 0.67166(2) 0.455790(19) 0.02334(9) Uani 1 1 d . . . Cl1 Cl 0.45820(9) 0.57304(9) 0.64306(7) 0.0375(2) Uani 1 1 d . . . Cl2 Cl 0.27950(8) 0.77827(10) 0.42810(7) 0.0419(2) Uani 1 1 d . . . N N 0.6772(3) 0.5820(3) 0.4735(2) 0.0271(6) Uani 1 1 d . . . P P 0.50252(7) 0.77889(7) 0.28194(6) 0.02220(18) Uani 1 1 d . . . O O 0.8724(2) 0.4920(3) 0.4353(2) 0.0384(6) Uani 1 1 d . . . S1 S 0.86086(8) 0.55204(8) 0.20540(7) 0.0339(2) Uani 1 1 d . . . S2 S 0.63436(8) 0.73324(9) 0.07807(7) 0.0327(2) Uani 1 1 d . . . S3 S 1.02650(8) 0.62466(9) -0.01385(7) 0.0324(2) Uani 1 1 d . . . S4 S 0.79072(8) 0.76852(9) -0.14452(7) 0.0333(2) Uani 1 1 d . . . S5 S 1.18081(10) 0.74604(13) -0.17543(9) 0.0491(3) Uani 1 1 d . . . S6 S 0.91597(10) 0.90335(10) -0.33197(9) 0.0472(3) Uani 1 1 d . . . C1 C 0.7387(3) 0.6156(3) 0.2800(3) 0.0264(7) Uani 1 1 d . . . C2 C 0.6369(3) 0.7008(3) 0.2212(3) 0.0251(7) Uani 1 1 d . . . C3 C 0.7958(3) 0.6580(3) 0.0776(3) 0.0294(7) Uani 1 1 d . . . C4 C 0.8620(3) 0.6810(3) -0.0130(3) 0.0286(7) Uani 1 1 d . . . C5 C 1.0332(4) 0.7384(3) -0.1370(3) 0.0315(8) Uani 1 1 d . . . C6 C 0.9252(4) 0.8045(3) -0.1974(3) 0.0321(8) Uani 1 1 d . . . C7 C 1.1736(5) 0.7896(6) -0.3238(4) 0.0597(14) Uani 1 1 d . . . H7A H 1.1950 0.8620 -0.3536 0.072 Uiso 1 1 calc R . . H7B H 1.2377 0.7286 -0.3443 0.072 Uiso 1 1 calc R . . C8 C 1.0546(5) 0.8101(6) -0.3780(4) 0.0594(14) Uani 1 1 d . . . H8A H 1.0443 0.7338 -0.3655 0.071 Uiso 1 1 calc R . . H8B H 1.0593 0.8469 -0.4567 0.071 Uiso 1 1 calc R . . C9 C 0.7558(3) 0.5663(3) 0.3996(3) 0.0264(7) Uani 1 1 d . . . C10 C 0.8685(4) 0.4378(4) 0.5552(3) 0.0438(10) Uani 1 1 d . . . H10A H 0.9395 0.4374 0.5929 0.053 Uiso 1 1 calc R . . H10B H 0.8678 0.3570 0.5751 0.053 Uiso 1 1 calc R . . C11 C 0.7461(4) 0.5179(4) 0.5836(3) 0.0368(8) Uani 1 1 d . . . H11 H 0.7004 0.4691 0.6336 0.044 Uiso 1 1 calc R . . C12 C 0.7626(6) 0.6046(6) 0.6325(5) 0.0667(15) Uani 1 1 d . . . H12A H 0.6824 0.6518 0.6477 0.100 Uiso 1 1 calc R . . H12B H 0.8028 0.6555 0.5813 0.100 Uiso 1 1 calc R . . H12C H 0.8132 0.5617 0.6997 0.100 Uiso 1 1 calc R . . C13 C 0.5226(3) 0.9193(3) 0.2708(3) 0.0286(7) Uani 1 1 d . . . C14 C 0.4743(4) 0.9683(4) 0.3525(3) 0.0411(9) Uani 1 1 d . . . H14 H 0.4360 0.9281 0.4116 0.049 Uiso 1 1 calc R . . C15 C 0.4835(5) 1.0771(4) 0.3456(4) 0.0492(11) Uani 1 1 d . . . H15 H 0.4510 1.1097 0.4000 0.059 Uiso 1 1 calc R . . C16 C 0.5409(5) 1.1374(4) 0.2576(4) 0.0473(10) Uani 1 1 d . . . H16 H 0.5473 1.2099 0.2535 0.057 Uiso 1 1 calc R . . C17 C 0.5879(4) 1.0904(4) 0.1772(4) 0.0486(11) Uani 1 1 d . . . H17 H 0.6259 1.1313 0.1184 0.058 Uiso 1 1 calc R . . C18 C 0.5795(4) 0.9812(4) 0.1825(4) 0.0390(9) Uani 1 1 d . . . H18 H 0.6116 0.9497 0.1273 0.047 Uiso 1 1 calc R . . C19 C 0.3751(3) 0.8159(3) 0.1847(3) 0.0250(7) Uani 1 1 d . . . C20 C 0.3050(4) 0.9337(4) 0.1302(3) 0.0377(8) Uani 1 1 d . . . H20 H 0.3261 0.9945 0.1404 0.045 Uiso 1 1 calc R . . C21 C 0.2035(4) 0.9609(4) 0.0606(4) 0.0470(10) Uani 1 1 d . . . H21 H 0.1567 1.0398 0.0242 0.056 Uiso 1 1 calc R . . C22 C 0.1726(4) 0.8705(5) 0.0457(3) 0.0451(10) Uani 1 1 d . . . H22 H 0.1039 0.8885 0.0001 0.054 Uiso 1 1 calc R . . C23 C 0.2437(4) 0.7527(4) 0.0986(4) 0.0449(10) Uani 1 1 d . . . H23 H 0.2233 0.6922 0.0870 0.054 Uiso 1 1 calc R . . C24 C 0.3445(4) 0.7249(4) 0.1685(3) 0.0332(8) Uani 1 1 d . . . H24 H 0.3914 0.6460 0.2044 0.040 Uiso 1 1 calc R . . C25 C 0.9317(7) 0.8961(6) 0.2737(6) 0.0727(16) Uani 1 1 d . . . H25A H 1.0175 0.8865 0.2895 0.087 Uiso 1 1 calc R . . H25B H 0.8926 0.9768 0.2247 0.087 Uiso 1 1 calc R . . Cl3 Cl 0.92909(14) 0.79617(13) 0.20865(13) 0.0672(3) Uani 1 1 d . . . Cl4 Cl 0.8531(2) 0.8721(2) 0.39577(14) 0.0936(5) Uani 1 1 d . . . OWA O 0.6249(4) 0.5438(3) 0.9240(3) 0.0279(8) Uani 0.70 1 d P . . OWB O 0.5428(7) 0.5490(6) 0.9325(5) 0.0138(13) Uiso 0.30 1 d P . . 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 Pd 0.02161(13) 0.02600(15) 0.01849(13) -0.00492(10) 0.00344(9) -0.00606(10) Cl1 0.0363(5) 0.0395(5) 0.0242(4) -0.0014(4) 0.0076(3) -0.0075(4) Cl2 0.0250(4) 0.0569(6) 0.0279(4) -0.0089(4) 0.0062(3) 0.0000(4) N 0.0246(14) 0.0304(15) 0.0230(13) -0.0042(12) -0.0011(11) -0.0094(12) P 0.0195(4) 0.0251(4) 0.0186(4) -0.0058(3) 0.0021(3) -0.0049(3) O 0.0233(12) 0.0422(15) 0.0329(13) -0.0005(12) -0.0016(10) -0.0016(11) S1 0.0261(4) 0.0344(5) 0.0315(4) -0.0093(4) 0.0077(3) -0.0009(4) S2 0.0248(4) 0.0457(5) 0.0219(4) -0.0124(4) 0.0038(3) -0.0040(4) S3 0.0252(4) 0.0368(5) 0.0306(4) -0.0090(4) 0.0063(3) -0.0079(4) S4 0.0262(4) 0.0409(5) 0.0294(4) -0.0120(4) 0.0053(3) -0.0074(4) S5 0.0369(5) 0.0828(8) 0.0349(5) -0.0184(5) 0.0111(4) -0.0322(6) S6 0.0403(5) 0.0457(6) 0.0349(5) -0.0001(4) 0.0083(4) -0.0036(5) C1 0.0198(15) 0.0309(18) 0.0269(16) -0.0102(14) 0.0045(12) -0.0068(13) C2 0.0226(15) 0.0293(17) 0.0215(14) -0.0072(13) 0.0044(12) -0.0081(13) C3 0.0263(16) 0.0313(18) 0.0295(17) -0.0130(15) 0.0058(14) -0.0061(14) C4 0.0266(16) 0.0291(18) 0.0312(17) -0.0148(15) 0.0062(14) -0.0067(14) C5 0.0338(18) 0.038(2) 0.0283(17) -0.0158(16) 0.0091(14) -0.0164(16) C6 0.0342(19) 0.0324(19) 0.0277(16) -0.0105(15) 0.0081(14) -0.0095(15) C7 0.041(2) 0.080(4) 0.037(2) -0.016(2) 0.0137(19) -0.001(2) C8 0.050(3) 0.084(4) 0.032(2) -0.022(2) 0.0090(19) -0.005(2) C9 0.0185(15) 0.0283(17) 0.0275(16) -0.0043(14) -0.0010(12) -0.0063(13) C10 0.0292(19) 0.050(3) 0.0322(19) 0.0061(18) -0.0056(15) -0.0073(17) C11 0.0321(19) 0.045(2) 0.0244(16) -0.0008(16) -0.0042(14) -0.0111(17) C12 0.070(3) 0.090(4) 0.046(3) -0.028(3) -0.012(2) -0.025(3) C13 0.0270(17) 0.0310(18) 0.0274(16) -0.0093(14) -0.0018(13) -0.0089(14) C14 0.055(2) 0.039(2) 0.0298(18) -0.0120(17) 0.0020(17) -0.0161(19) C15 0.070(3) 0.039(2) 0.042(2) -0.019(2) -0.001(2) -0.017(2) C16 0.051(2) 0.032(2) 0.057(3) -0.008(2) -0.012(2) -0.0154(19) C17 0.046(2) 0.043(2) 0.057(3) -0.008(2) 0.008(2) -0.025(2) C18 0.040(2) 0.035(2) 0.043(2) -0.0123(18) 0.0112(17) -0.0167(17) C19 0.0220(15) 0.0317(18) 0.0188(14) -0.0086(13) 0.0031(12) -0.0061(13) C20 0.037(2) 0.0309(19) 0.039(2) -0.0099(17) -0.0082(16) -0.0024(16) C21 0.038(2) 0.044(2) 0.043(2) -0.0098(19) -0.0138(18) 0.0050(18) C22 0.0280(19) 0.067(3) 0.036(2) -0.019(2) -0.0076(16) -0.0066(19) C23 0.040(2) 0.056(3) 0.045(2) -0.019(2) -0.0035(18) -0.021(2) C24 0.0337(19) 0.0340(19) 0.0291(17) -0.0059(15) -0.0031(14) -0.0118(15) C25 0.094(4) 0.060(3) 0.070(3) -0.014(3) -0.004(3) -0.040(3) Cl3 0.0716(8) 0.0635(8) 0.0701(8) -0.0195(7) -0.0029(7) -0.0286(7) Cl4 0.0975(12) 0.1117(14) 0.0597(8) -0.0225(9) -0.0038(8) -0.0245(11) OWA 0.051(2) 0.0047(14) 0.0260(16) -0.0071(12) -0.0208(15) -0.0008(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd N 2.054(3) . ? Pd P 2.2194(8) . ? Pd Cl2 2.2927(9) . ? Pd Cl1 2.3742(8) . ? N C9 1.281(5) . ? N C11 1.500(5) . ? P C2 1.814(3) . ? P C19 1.818(3) . ? P C13 1.825(4) . ? O C9 1.348(4) . ? O C10 1.470(5) . ? S1 C3 1.754(4) . ? S1 C1 1.764(3) . ? S2 C2 1.754(3) . ? S2 C3 1.766(4) . ? S3 C5 1.761(4) . ? S3 C4 1.767(4) . ? S4 C4 1.758(4) . ? S4 C6 1.762(4) . ? S5 C5 1.738(4) . ? S5 C7 1.806(5) . ? S6 C6 1.748(4) . ? S6 C8 1.830(5) . ? C1 C2 1.349(5) . ? C1 C9 1.457(5) . ? C3 C4 1.345(5) . ? C5 C6 1.352(6) . ? C7 C8 1.471(8) . ? C10 C11 1.533(6) . ? C11 C12 1.508(8) . ? C13 C14 1.396(6) . ? C13 C18 1.397(6) . ? C14 C15 1.390(7) . ? C15 C16 1.390(8) . ? C16 C17 1.363(8) . ? C17 C18 1.398(7) . ? C19 C20 1.390(5) . ? C19 C24 1.393(6) . ? C20 C21 1.389(6) . ? C21 C22 1.379(8) . ? C22 C23 1.390(7) . ? C23 C24 1.384(6) . ? C25 Cl4 1.741(8) . ? C25 Cl3 1.754(7) . ? OWA OWB 0.914(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N Pd P 92.15(8) . . ? N Pd Cl2 177.17(8) . . ? P Pd Cl2 85.08(3) . . ? N Pd Cl1 92.30(8) . . ? P Pd Cl1 174.59(3) . . ? Cl2 Pd Cl1 90.43(3) . . ? C9 N C11 107.7(3) . . ? C9 N Pd 129.4(2) . . ? C11 N Pd 122.8(2) . . ? C2 P C19 102.77(15) . . ? C2 P C13 106.46(16) . . ? C19 P C13 106.23(16) . . ? C2 P Pd 111.00(11) . . ? C19 P Pd 117.78(11) . . ? C13 P Pd 111.69(12) . . ? C9 O C10 106.2(3) . . ? C3 S1 C1 93.70(16) . . ? C2 S2 C3 93.46(16) . . ? C5 S3 C4 93.22(18) . . ? C4 S4 C6 93.67(17) . . ? C5 S5 C7 104.5(2) . . ? C6 S6 C8 96.1(2) . . ? C2 C1 C9 126.6(3) . . ? C2 C1 S1 117.0(3) . . ? C9 C1 S1 116.3(2) . . ? C1 C2 S2 117.2(2) . . ? C1 C2 P 123.8(2) . . ? S2 C2 P 118.95(19) . . ? C4 C3 S1 123.5(3) . . ? C4 C3 S2 122.5(3) . . ? S1 C3 S2 113.97(19) . . ? C3 C4 S4 122.4(3) . . ? C3 C4 S3 124.3(3) . . ? S4 C4 S3 113.21(19) . . ? C6 C5 S5 126.0(3) . . ? C6 C5 S3 117.1(3) . . ? S5 C5 S3 116.5(2) . . ? C5 C6 S6 124.1(3) . . ? C5 C6 S4 116.5(3) . . ? S6 C6 S4 118.5(2) . . ? C8 C7 S5 117.6(3) . . ? C7 C8 S6 115.2(4) . . ? N C9 O 116.9(3) . . ? N C9 C1 129.7(3) . . ? O C9 C1 113.4(3) . . ? O C10 C11 103.7(3) . . ? N C11 C12 110.9(4) . . ? N C11 C10 102.1(3) . . ? C12 C11 C10 114.2(4) . . ? C14 C13 C18 119.2(4) . . ? C14 C13 P 117.9(3) . . ? C18 C13 P 122.9(3) . . ? C15 C14 C13 120.0(4) . . ? C14 C15 C16 120.3(4) . . ? C17 C16 C15 120.1(4) . . ? C16 C17 C18 120.5(4) . . ? C13 C18 C17 119.9(4) . . ? C20 C19 C24 119.9(3) . . ? C20 C19 P 120.7(3) . . ? C24 C19 P 119.4(3) . . ? C21 C20 C19 120.3(4) . . ? C22 C21 C20 119.7(4) . . ? C21 C22 C23 120.3(4) . . ? C24 C23 C22 120.4(4) . . ? C23 C24 C19 119.5(4) . . ? Cl4 C25 Cl3 110.9(4) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 1.443 _refine_diff_density_min -0.973 _refine_diff_density_rms 0.086