# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email rodembusch@iq.ufrgs.br _publ_contact_author_name 'Rodembusch, Fabiano' loop_ _publ_author_name 'Fabiano Mancilha' 'Laurent Barloy' 'Fabiano Rodembusch' 'Jairton Dupont' 'Michel Pfeffer' data_2c _database_code_depnum_ccdc_archive 'CCDC 821838' #TrackingRef '- crystal structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 Br2 N4 O6 Pd2 S2, 2(C H2 Cl2)' _chemical_formula_sum 'C32 H26 Br2 Cl4 N4 O6 Pd2 S2' _chemical_formula_weight 1141.11 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' Br Br -0.2901 2.4595 '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' 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 10.8302(2) _cell_length_b 26.1898(5) _cell_length_c 13.3993(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3800.59(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 33557 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 3.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.52407 _exptl_absorpt_correction_T_max 0.66192 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33822 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 30.03 _reflns_number_total 5558 _reflns_number_gt 4263 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0772P)^2^+1.1029P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5558 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _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 C1 C -0.0501(4) 0.02465(15) 0.3775(3) 0.0212(8) Uani 1 1 d . . . C2 C -0.1612(4) 0.05373(16) 0.3792(3) 0.0232(8) Uani 1 1 d . . . C3 C -0.1536(4) 0.10780(17) 0.3746(3) 0.0299(9) Uani 1 1 d . . . C4 C -0.0405(4) 0.12956(18) 0.3703(3) 0.0351(10) Uani 1 1 d . . . H4 H -0.0342 0.1657 0.3675 0.042 Uiso 1 1 calc R . . C5 C 0.0693(4) 0.09977(17) 0.3697(3) 0.0293(9) Uani 1 1 d . . . H5 H 0.1463 0.1172 0.3685 0.035 Uiso 1 1 calc R . . C6 C 0.0705(4) 0.04667(16) 0.3709(3) 0.0215(8) Uani 1 1 d . . . C7 C 0.1824(4) 0.01589(15) 0.3681(3) 0.0219(8) Uani 1 1 d . . . C8 C 0.2980(4) 0.04080(17) 0.3674(3) 0.0261(8) Uani 1 1 d . . . H8 H 0.2989 0.0770 0.3641 0.031 Uiso 1 1 calc R . . C9 C 0.4096(4) 0.01566(18) 0.3712(3) 0.0282(9) Uani 1 1 d . . . H9 H 0.4853 0.0340 0.3694 0.034 Uiso 1 1 calc R . . C10 C 0.4081(4) -0.03725(16) 0.3778(3) 0.0244(8) Uani 1 1 d . . . C11 C 0.2968(4) -0.06347(17) 0.3753(3) 0.0240(8) Uani 1 1 d . . . H11 H 0.2977 -0.0997 0.3788 0.029 Uiso 1 1 calc R . . C12 C 0.1840(4) -0.03845(15) 0.3678(3) 0.0205(7) Uani 1 1 d . . . C13 C 0.5243(4) -0.1131(2) 0.4057(5) 0.0457(12) Uani 1 1 d . . . H13A H 0.4791 -0.1201 0.4676 0.069 Uiso 1 1 calc R . . H13B H 0.6100 -0.1245 0.4129 0.069 Uiso 1 1 calc R . . H13C H 0.4853 -0.1316 0.3504 0.069 Uiso 1 1 calc R . . C14 C -0.1620(4) -0.15791(15) 0.2761(3) 0.0261(8) Uani 1 1 d . . . C15 C -0.2472(5) -0.20321(19) 0.2948(4) 0.0421(11) Uani 1 1 d . . . H15A H -0.2676 -0.2050 0.3660 0.063 Uiso 1 1 calc R . . H15B H -0.2057 -0.2348 0.2746 0.063 Uiso 1 1 calc R . . H15C H -0.3232 -0.1990 0.2560 0.063 Uiso 1 1 calc R . . C16 C 0.0513(6) -0.2370(2) 0.4632(5) 0.0597(16) Uani 1 1 d . . . H16A H 0.0221 -0.2077 0.4228 0.072 Uiso 1 1 calc R . . H16B H 0.1267 -0.2262 0.4993 0.072 Uiso 1 1 calc R . . Br1 Br -0.29981(5) 0.14680(2) 0.36795(4) 0.04465(16) Uani 1 1 d . . . Cl1 Cl -0.06415(17) -0.25450(6) 0.55005(12) 0.0660(4) Uani 1 1 d . . . Cl2 Cl 0.0860(2) -0.28844(8) 0.38461(14) 0.0830(6) Uani 1 1 d . . . N1 N -0.0747(3) -0.02538(13) 0.3815(2) 0.0202(6) Uani 1 1 d . . . N2 N -0.2656(3) 0.02566(14) 0.3840(2) 0.0245(7) Uani 1 1 d . . . O1 O 0.5219(3) -0.05990(12) 0.3857(3) 0.0327(7) Uani 1 1 d . . . O2 O -0.1185(3) -0.13556(11) 0.3503(2) 0.0299(6) Uani 1 1 d . . . O3 O -0.1429(3) -0.14637(10) 0.1853(2) 0.0280(6) Uani 1 1 d . . . Pd1 Pd 0.03745(3) -0.083857(11) 0.35400(2) 0.01980(11) Uani 1 1 d . . . S1 S -0.22551(9) -0.03309(4) 0.38593(7) 0.0239(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0196(19) 0.0264(19) 0.0175(17) 0.0011(14) 0.0005(13) 0.0006(15) C2 0.0177(18) 0.033(2) 0.0193(17) 0.0024(15) 0.0033(14) 0.0025(16) C3 0.026(2) 0.034(2) 0.030(2) -0.0025(17) 0.0056(16) 0.0080(18) C4 0.036(3) 0.029(2) 0.040(3) -0.0014(18) 0.0045(19) 0.0036(19) C5 0.021(2) 0.031(2) 0.036(2) -0.0031(17) 0.0019(17) -0.0008(17) C6 0.0161(18) 0.030(2) 0.0182(18) -0.0024(14) -0.0011(13) 0.0007(15) C7 0.0197(19) 0.0288(19) 0.0172(18) 0.0000(14) 0.0005(14) -0.0019(16) C8 0.019(2) 0.030(2) 0.029(2) 0.0012(16) -0.0019(15) -0.0044(16) C9 0.0156(19) 0.040(2) 0.029(2) 0.0002(17) 0.0006(15) -0.0058(17) C10 0.0132(18) 0.034(2) 0.0260(19) 0.0009(15) -0.0005(14) 0.0019(15) C11 0.0171(19) 0.031(2) 0.0240(19) -0.0003(15) 0.0004(14) -0.0017(16) C12 0.0152(18) 0.0297(19) 0.0166(17) 0.0009(13) -0.0003(13) -0.0073(15) C13 0.020(2) 0.044(3) 0.073(4) 0.006(3) 0.000(2) 0.007(2) C14 0.0132(18) 0.0248(18) 0.040(2) 0.0022(16) 0.0034(15) -0.0005(14) C15 0.033(3) 0.036(2) 0.057(3) -0.002(2) 0.009(2) -0.013(2) C16 0.060(4) 0.055(4) 0.064(4) 0.005(3) -0.001(3) -0.020(3) Br1 0.0333(3) 0.0397(3) 0.0610(3) 0.0036(2) 0.0085(2) 0.0165(2) Cl1 0.0740(11) 0.0530(8) 0.0711(10) -0.0057(7) 0.0149(8) -0.0234(8) Cl2 0.0917(15) 0.0781(12) 0.0791(11) -0.0173(9) 0.0290(11) -0.0358(11) N1 0.0131(15) 0.0293(17) 0.0180(15) -0.0020(12) -0.0002(11) 0.0000(13) N2 0.0158(16) 0.0351(19) 0.0226(16) 0.0002(13) 0.0007(12) 0.0052(14) O1 0.0120(14) 0.0376(17) 0.0484(18) 0.0024(15) -0.0005(12) 0.0020(12) O2 0.0235(16) 0.0307(15) 0.0355(16) 0.0005(12) 0.0048(12) -0.0053(12) O3 0.0211(15) 0.0264(14) 0.0364(16) 0.0004(12) -0.0028(12) -0.0047(11) Pd1 0.01375(16) 0.02401(16) 0.02164(18) 0.00031(10) -0.00005(10) -0.00057(10) S1 0.0139(5) 0.0325(5) 0.0254(5) -0.0001(4) 0.0012(3) -0.0002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.338(5) . ? C1 C2 1.424(5) . ? C1 C6 1.431(5) . ? C2 N2 1.350(5) . ? C2 C3 1.420(6) . ? C3 C4 1.352(6) . ? C3 Br1 1.886(4) . ? C4 C5 1.422(6) . ? C4 H4 0.9500 . ? C5 C6 1.391(6) . ? C5 H5 0.9500 . ? C6 C7 1.456(6) . ? C7 C8 1.412(5) . ? C7 C12 1.423(6) . ? C8 C9 1.377(6) . ? C8 H8 0.9500 . ? C9 C10 1.389(6) . ? C9 H9 0.9500 . ? C10 O1 1.372(5) . ? C10 C11 1.388(5) . ? C11 C12 1.390(5) . ? C11 H11 0.9500 . ? C12 Pd1 1.992(4) . ? C13 O1 1.420(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O2 1.247(5) . ? C14 O3 1.271(5) . ? C14 C15 1.524(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 Cl2 1.751(6) . ? C16 Cl1 1.769(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? N1 S1 1.647(3) . ? N1 Pd1 1.989(3) . ? N2 S1 1.599(4) . ? O2 Pd1 2.165(3) . ? O3 Pd1 2.064(3) 4 ? Pd1 O3 2.064(3) 4 ? Pd1 Pd1 2.9026(6) 4 ? 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 N1 C1 C2 110.8(3) . . ? N1 C1 C6 125.4(4) . . ? C2 C1 C6 123.8(4) . . ? N2 C2 C3 126.4(4) . . ? N2 C2 C1 114.6(4) . . ? C3 C2 C1 118.9(4) . . ? C4 C3 C2 118.3(4) . . ? C4 C3 Br1 122.0(4) . . ? C2 C3 Br1 119.6(3) . . ? C3 C4 C5 121.8(4) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 123.8(4) . . ? C6 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C5 C6 C1 113.3(4) . . ? C5 C6 C7 124.1(4) . . ? C1 C6 C7 122.6(4) . . ? C8 C7 C12 116.8(4) . . ? C8 C7 C6 118.8(4) . . ? C12 C7 C6 124.3(4) . . ? C9 C8 C7 123.8(4) . . ? C9 C8 H8 118.1 . . ? C7 C8 H8 118.1 . . ? C8 C9 C10 118.0(4) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? O1 C10 C11 124.6(4) . . ? O1 C10 C9 115.2(4) . . ? C11 C10 C9 120.2(4) . . ? C10 C11 C12 122.1(4) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C11 C12 C7 118.8(4) . . ? C11 C12 Pd1 115.2(3) . . ? C7 C12 Pd1 126.0(3) . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 126.2(4) . . ? O2 C14 C15 117.6(4) . . ? O3 C14 C15 116.2(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Cl2 C16 Cl1 110.4(3) . . ? Cl2 C16 H16A 109.6 . . ? Cl1 C16 H16A 109.6 . . ? Cl2 C16 H16B 109.6 . . ? Cl1 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C1 N1 S1 108.6(3) . . ? C1 N1 Pd1 128.7(3) . . ? S1 N1 Pd1 121.18(19) . . ? C2 N2 S1 107.3(3) . . ? C10 O1 C13 117.1(3) . . ? C14 O2 Pd1 127.4(3) . . ? C14 O3 Pd1 121.5(3) . 4 ? N1 Pd1 C12 90.55(15) . . ? N1 Pd1 O3 174.66(12) . 4 ? C12 Pd1 O3 93.24(14) . 4 ? N1 Pd1 O2 90.54(12) . . ? C12 Pd1 O2 175.55(13) . . ? O3 Pd1 O2 85.96(11) 4 . ? N1 Pd1 Pd1 90.43(9) . 4 ? C12 Pd1 Pd1 108.19(10) . 4 ? O3 Pd1 Pd1 84.82(8) 4 4 ? O2 Pd1 Pd1 76.12(7) . 4 ? N2 S1 N1 98.67(18) . . ? 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 C1 C2 N2 -0.2(5) . . . . ? C6 C1 C2 N2 178.9(3) . . . . ? N1 C1 C2 C3 -179.5(3) . . . . ? C6 C1 C2 C3 -0.4(5) . . . . ? N2 C2 C3 C4 179.9(4) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? N2 C2 C3 Br1 -3.3(5) . . . . ? C1 C2 C3 Br1 175.9(3) . . . . ? C2 C3 C4 C5 0.3(6) . . . . ? Br1 C3 C4 C5 -176.4(3) . . . . ? C3 C4 C5 C6 1.8(7) . . . . ? C4 C5 C6 C1 -2.9(5) . . . . ? C4 C5 C6 C7 178.6(4) . . . . ? N1 C1 C6 C5 -178.9(4) . . . . ? C2 C1 C6 C5 2.2(5) . . . . ? N1 C1 C6 C7 -0.3(6) . . . . ? C2 C1 C6 C7 -179.2(3) . . . . ? C5 C6 C7 C8 2.1(5) . . . . ? C1 C6 C7 C8 -176.3(3) . . . . ? C5 C6 C7 C12 -179.1(4) . . . . ? C1 C6 C7 C12 2.5(5) . . . . ? C12 C7 C8 C9 -3.2(5) . . . . ? C6 C7 C8 C9 175.7(4) . . . . ? C7 C8 C9 C10 -1.1(6) . . . . ? C8 C9 C10 O1 -177.3(3) . . . . ? C8 C9 C10 C11 3.3(6) . . . . ? O1 C10 C11 C12 179.6(4) . . . . ? C9 C10 C11 C12 -1.1(6) . . . . ? C10 C11 C12 C7 -3.4(5) . . . . ? C10 C11 C12 Pd1 175.1(3) . . . . ? C8 C7 C12 C11 5.3(5) . . . . ? C6 C7 C12 C11 -173.6(3) . . . . ? C8 C7 C12 Pd1 -173.0(3) . . . . ? C6 C7 C12 Pd1 8.2(5) . . . . ? C2 C1 N1 S1 0.4(4) . . . . ? C6 C1 N1 S1 -178.6(3) . . . . ? C2 C1 N1 Pd1 166.2(3) . . . . ? C6 C1 N1 Pd1 -12.9(5) . . . . ? C3 C2 N2 S1 179.1(3) . . . . ? C1 C2 N2 S1 -0.1(4) . . . . ? C11 C10 O1 C13 -8.6(6) . . . . ? C9 C10 O1 C13 172.0(4) . . . . ? O3 C14 O2 Pd1 -17.3(6) . . . . ? C15 C14 O2 Pd1 163.2(3) . . . . ? O2 C14 O3 Pd1 -2.8(6) . . . 4 ? C15 C14 O3 Pd1 176.7(3) . . . 4 ? C1 N1 Pd1 C12 17.3(3) . . . . ? S1 N1 Pd1 C12 -178.6(2) . . . . ? C1 N1 Pd1 O2 -167.0(3) . . . . ? S1 N1 Pd1 O2 -2.9(2) . . . . ? C1 N1 Pd1 Pd1 -90.9(3) . . . 4 ? S1 N1 Pd1 Pd1 73.24(18) . . . 4 ? C11 C12 Pd1 N1 167.2(3) . . . . ? C7 C12 Pd1 N1 -14.5(3) . . . . ? C11 C12 Pd1 O3 -16.6(3) . . . 4 ? C7 C12 Pd1 O3 161.7(3) . . . 4 ? C11 C12 Pd1 Pd1 -102.2(3) . . . 4 ? C7 C12 Pd1 Pd1 76.1(3) . . . 4 ? C14 O2 Pd1 N1 110.1(3) . . . . ? C14 O2 Pd1 O3 -65.9(3) . . . 4 ? C14 O2 Pd1 Pd1 19.8(3) . . . 4 ? C2 N2 S1 N1 0.3(3) . . . . ? C1 N1 S1 N2 -0.5(3) . . . . ? Pd1 N1 S1 N2 -167.47(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.900 _refine_diff_density_min -1.696 _refine_diff_density_rms 0.317 data_3c _database_code_depnum_ccdc_archive 'CCDC 821839' #TrackingRef '- crystal structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Br Cl N3 O Pd S' _chemical_formula_sum 'C18 H13 Br Cl N3 O Pd S' _chemical_formula_weight 541.13 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' Br Br -0.2901 2.4595 '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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6025(4) _cell_length_b 10.4897(4) _cell_length_c 10.9885(3) _cell_angle_alpha 77.842(2) _cell_angle_beta 85.148(2) _cell_angle_gamma 67.469(2) _cell_volume 895.34(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5844 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 3.546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.35123 _exptl_absorpt_correction_T_max 0.43655 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10301 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 29.99 _reflns_number_total 5192 _reflns_number_gt 4629 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0301P)^2^+0.6151P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5192 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.2639(3) -0.0111(2) 0.5646(2) 0.0182(4) Uani 1 1 d . . . C2 C 0.3477(3) -0.0865(2) 0.6811(2) 0.0195(4) Uani 1 1 d . . . C3 C 0.4997(3) -0.2050(2) 0.6814(2) 0.0207(4) Uani 1 1 d . . . C4 C 0.5640(3) -0.2409(3) 0.5712(2) 0.0234(5) Uani 1 1 d . . . H4 H 0.6672 -0.3187 0.5699 0.028 Uiso 1 1 calc R . . C5 C 0.4798(3) -0.1640(2) 0.4575(2) 0.0223(5) Uani 1 1 d . . . H5 H 0.5306 -0.1930 0.3827 0.027 Uiso 1 1 calc R . . C6 C 0.3283(3) -0.0495(2) 0.4485(2) 0.0182(4) Uani 1 1 d . . . C7 C 0.2361(3) 0.0245(2) 0.3307(2) 0.0190(4) Uani 1 1 d . . . C8 C 0.3030(3) -0.0304(3) 0.2227(2) 0.0262(5) Uani 1 1 d . . . H8 H 0.4086 -0.1070 0.2286 0.031 Uiso 1 1 calc R . . C9 C 0.2233(3) 0.0212(3) 0.1093(2) 0.0265(5) Uani 1 1 d . . . H9 H 0.2743 -0.0166 0.0380 0.032 Uiso 1 1 calc R . . C10 C 0.0665(3) 0.1300(2) 0.1016(2) 0.0208(4) Uani 1 1 d . . . C11 C -0.0013(3) 0.1893(2) 0.2044(2) 0.0195(4) Uani 1 1 d . . . H11 H -0.1082 0.2643 0.1971 0.023 Uiso 1 1 calc R . . C12 C 0.0827(3) 0.1425(2) 0.3202(2) 0.0183(4) Uani 1 1 d . . . C13 C -0.1713(4) 0.2839(3) -0.0264(2) 0.0327(6) Uani 1 1 d . . . H13A H -0.2532 0.2532 0.0263 0.049 Uiso 1 1 calc R . . H13B H -0.2064 0.3087 -0.1136 0.049 Uiso 1 1 calc R . . H13C H -0.1653 0.3661 -0.0012 0.049 Uiso 1 1 calc R . . C14 C -0.0933(3) 0.4971(3) 0.2434(2) 0.0264(5) Uani 1 1 d . . . H14 H 0.0258 0.4682 0.2413 0.032 Uiso 1 1 calc R . . C15 C -0.1887(4) 0.6126(3) 0.1572(2) 0.0327(6) Uani 1 1 d . . . H15 H -0.1357 0.6632 0.0979 0.039 Uiso 1 1 calc R . . C16 C -0.3605(4) 0.6530(3) 0.1586(2) 0.0337(6) Uani 1 1 d . . . H16 H -0.4277 0.7298 0.0985 0.040 Uiso 1 1 calc R . . C17 C -0.4346(4) 0.5807(3) 0.2485(2) 0.0321(6) Uani 1 1 d . . . H17 H -0.5534 0.6078 0.2520 0.038 Uiso 1 1 calc R . . C18 C -0.3331(3) 0.4681(3) 0.3334(2) 0.0249(5) Uani 1 1 d . . . H18 H -0.3842 0.4195 0.3964 0.030 Uiso 1 1 calc R . . Br1 Br 0.60559(3) -0.30822(3) 0.83410(2) 0.02974(7) Uani 1 1 d . . . Cl1 Cl -0.16033(9) 0.38399(6) 0.61556(5) 0.02902(14) Uani 1 1 d . . . N1 N 0.1241(3) 0.0986(2) 0.58182(17) 0.0194(4) Uani 1 1 d . . . N2 N 0.2694(3) -0.0314(2) 0.77974(18) 0.0234(4) Uani 1 1 d . . . N3 N -0.1645(3) 0.4251(2) 0.32977(18) 0.0195(4) Uani 1 1 d . . . O1 O -0.0093(2) 0.17214(19) -0.01276(15) 0.0259(4) Uani 1 1 d . . . Pd1 Pd -0.02306(2) 0.254006(17) 0.454478(14) 0.01732(6) Uani 1 1 d . . . S1 S 0.10413(8) 0.10362(6) 0.73157(5) 0.02393(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0218(11) 0.0148(10) 0.0177(10) -0.0013(7) -0.0025(8) -0.0069(9) C2 0.0237(12) 0.0179(10) 0.0164(10) -0.0024(8) -0.0036(8) -0.0071(9) C3 0.0223(11) 0.0196(10) 0.0188(10) 0.0019(8) -0.0073(8) -0.0078(9) C4 0.0224(12) 0.0199(11) 0.0239(11) -0.0035(9) -0.0054(9) -0.0029(9) C5 0.0244(12) 0.0206(11) 0.0193(10) -0.0046(8) -0.0024(9) -0.0048(9) C6 0.0224(11) 0.0166(10) 0.0160(9) -0.0031(7) -0.0036(8) -0.0071(9) C7 0.0230(11) 0.0171(10) 0.0158(9) -0.0032(8) -0.0024(8) -0.0058(9) C8 0.0270(13) 0.0231(12) 0.0219(11) -0.0077(9) -0.0034(9) 0.0002(10) C9 0.0345(14) 0.0238(12) 0.0169(10) -0.0088(9) -0.0014(9) -0.0035(11) C10 0.0270(12) 0.0200(11) 0.0149(10) -0.0007(8) -0.0050(8) -0.0086(9) C11 0.0216(11) 0.0190(10) 0.0172(10) -0.0038(8) -0.0032(8) -0.0061(9) C12 0.0222(11) 0.0157(10) 0.0168(10) -0.0047(8) -0.0024(8) -0.0056(9) C13 0.0280(14) 0.0385(15) 0.0239(12) -0.0037(10) -0.0098(10) -0.0035(12) C14 0.0242(12) 0.0243(12) 0.0289(12) -0.0016(9) -0.0001(9) -0.0092(10) C15 0.0412(16) 0.0237(12) 0.0271(13) 0.0018(10) 0.0022(11) -0.0096(12) C16 0.0428(17) 0.0245(13) 0.0210(12) -0.0051(9) -0.0072(11) 0.0032(12) C17 0.0235(13) 0.0365(14) 0.0301(13) -0.0112(11) -0.0053(10) -0.0012(11) C18 0.0229(12) 0.0264(12) 0.0249(11) -0.0066(9) -0.0010(9) -0.0074(10) Br1 0.02912(14) 0.02978(14) 0.02121(12) 0.00263(9) -0.00729(10) -0.00355(11) Cl1 0.0341(3) 0.0241(3) 0.0193(3) -0.0083(2) 0.0001(2) 0.0016(2) N1 0.0229(10) 0.0181(9) 0.0144(8) -0.0024(7) -0.0030(7) -0.0045(8) N2 0.0285(11) 0.0227(10) 0.0175(9) -0.0028(7) -0.0024(8) -0.0080(9) N3 0.0210(10) 0.0152(9) 0.0207(9) -0.0036(7) -0.0034(7) -0.0042(8) O1 0.0301(10) 0.0289(9) 0.0144(7) -0.0042(6) -0.0067(6) -0.0050(8) Pd1 0.01951(9) 0.01501(9) 0.01502(9) -0.00331(6) -0.00177(6) -0.00328(7) S1 0.0293(3) 0.0224(3) 0.0144(2) -0.0039(2) -0.0014(2) -0.0029(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.341(3) . ? C1 C6 1.423(3) . ? C1 C2 1.441(3) . ? C2 N2 1.343(3) . ? C2 C3 1.417(3) . ? C3 C4 1.353(3) . ? C3 Br1 1.886(2) . ? C4 C5 1.421(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.479(3) . ? C7 C8 1.410(3) . ? C7 C12 1.414(3) . ? C8 C9 1.376(3) . ? C8 H8 0.9500 . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 O1 1.372(3) . ? C10 C11 1.382(3) . ? C11 C12 1.415(3) . ? C11 H11 0.9500 . ? C12 Pd1 2.015(2) . ? C13 O1 1.431(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N3 1.342(3) . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 C16 1.373(4) . ? C15 H15 0.9500 . ? C16 C17 1.381(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(4) . ? C17 H17 0.9500 . ? C18 N3 1.344(3) . ? C18 H18 0.9500 . ? Cl1 Pd1 2.4115(6) . ? N1 S1 1.6499(19) . ? N1 Pd1 1.9938(19) . ? N2 S1 1.605(2) . ? N3 Pd1 2.0376(19) . ? 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 N1 C1 C6 126.2(2) . . ? N1 C1 C2 111.02(19) . . ? C6 C1 C2 122.7(2) . . ? N2 C2 C3 127.1(2) . . ? N2 C2 C1 113.7(2) . . ? C3 C2 C1 119.2(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 Br1 122.01(18) . . ? C2 C3 Br1 119.38(17) . . ? C3 C4 C5 121.1(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 124.3(2) . . ? C6 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? C5 C6 C1 114.0(2) . . ? C5 C6 C7 124.0(2) . . ? C1 C6 C7 121.9(2) . . ? C8 C7 C12 118.1(2) . . ? C8 C7 C6 117.3(2) . . ? C12 C7 C6 124.5(2) . . ? C9 C8 C7 123.3(2) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? C8 C9 C10 118.4(2) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? O1 C10 C11 124.6(2) . . ? O1 C10 C9 115.4(2) . . ? C11 C10 C9 120.0(2) . . ? C10 C11 C12 122.4(2) . . ? C10 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C7 C12 C11 117.4(2) . . ? C7 C12 Pd1 125.54(16) . . ? C11 C12 Pd1 116.99(17) . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 121.8(2) . . ? N3 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 119.2(3) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 119.1(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? N3 C18 C17 122.1(2) . . ? N3 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C1 N1 S1 108.68(15) . . ? C1 N1 Pd1 128.71(15) . . ? S1 N1 Pd1 121.91(11) . . ? C2 N2 S1 108.41(16) . . ? C14 N3 C18 118.7(2) . . ? C14 N3 Pd1 121.54(17) . . ? C18 N3 Pd1 119.77(16) . . ? C10 O1 C13 117.91(19) . . ? N1 Pd1 C12 90.43(8) . . ? N1 Pd1 N3 174.54(8) . . ? C12 Pd1 N3 92.61(8) . . ? N1 Pd1 Cl1 89.98(6) . . ? C12 Pd1 Cl1 177.37(7) . . ? N3 Pd1 Cl1 87.19(6) . . ? N2 S1 N1 98.23(10) . . ? 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 C1 C2 N2 -0.2(3) . . . . ? C6 C1 C2 N2 178.2(2) . . . . ? N1 C1 C2 C3 -179.2(2) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? N2 C2 C3 C4 -176.8(2) . . . . ? C1 C2 C3 C4 2.1(3) . . . . ? N2 C2 C3 Br1 3.5(3) . . . . ? C1 C2 C3 Br1 -177.67(16) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? Br1 C3 C4 C5 178.22(18) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C4 C5 C6 C1 1.7(4) . . . . ? C4 C5 C6 C7 -176.0(2) . . . . ? N1 C1 C6 C5 177.1(2) . . . . ? C2 C1 C6 C5 -1.1(3) . . . . ? N1 C1 C6 C7 -5.1(4) . . . . ? C2 C1 C6 C7 176.7(2) . . . . ? C5 C6 C7 C8 3.5(3) . . . . ? C1 C6 C7 C8 -174.1(2) . . . . ? C5 C6 C7 C12 -179.1(2) . . . . ? C1 C6 C7 C12 3.3(3) . . . . ? C12 C7 C8 C9 -2.9(4) . . . . ? C6 C7 C8 C9 174.7(2) . . . . ? C7 C8 C9 C10 -2.1(4) . . . . ? C8 C9 C10 O1 -177.2(2) . . . . ? C8 C9 C10 C11 3.9(4) . . . . ? O1 C10 C11 C12 -179.5(2) . . . . ? C9 C10 C11 C12 -0.7(4) . . . . ? C8 C7 C12 C11 5.8(3) . . . . ? C6 C7 C12 C11 -171.6(2) . . . . ? C8 C7 C12 Pd1 -172.02(18) . . . . ? C6 C7 C12 Pd1 10.6(3) . . . . ? C10 C11 C12 C7 -4.3(3) . . . . ? C10 C11 C12 Pd1 173.78(18) . . . . ? N3 C14 C15 C16 -1.2(4) . . . . ? C14 C15 C16 C17 2.2(4) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? C16 C17 C18 N3 -1.3(4) . . . . ? C6 C1 N1 S1 -178.11(19) . . . . ? C2 C1 N1 S1 0.2(2) . . . . ? C6 C1 N1 Pd1 -7.7(4) . . . . ? C2 C1 N1 Pd1 170.56(16) . . . . ? C3 C2 N2 S1 178.9(2) . . . . ? C1 C2 N2 S1 0.0(3) . . . . ? C15 C14 N3 C18 -1.0(4) . . . . ? C15 C14 N3 Pd1 179.2(2) . . . . ? C17 C18 N3 C14 2.3(4) . . . . ? C17 C18 N3 Pd1 -177.87(19) . . . . ? C11 C10 O1 C13 -1.1(4) . . . . ? C9 C10 O1 C13 180.0(2) . . . . ? C1 N1 Pd1 C12 15.6(2) . . . . ? S1 N1 Pd1 C12 -175.19(14) . . . . ? C1 N1 Pd1 Cl1 -167.0(2) . . . . ? S1 N1 Pd1 Cl1 2.21(12) . . . . ? C7 C12 Pd1 N1 -16.4(2) . . . . ? C11 C12 Pd1 N1 165.73(18) . . . . ? C7 C12 Pd1 N3 159.1(2) . . . . ? C11 C12 Pd1 N3 -18.81(18) . . . . ? C14 N3 Pd1 C12 -64.9(2) . . . . ? C18 N3 Pd1 C12 115.31(18) . . . . ? C14 N3 Pd1 Cl1 117.74(19) . . . . ? C18 N3 Pd1 Cl1 -62.07(17) . . . . ? C2 N2 S1 N1 0.07(18) . . . . ? C1 N1 S1 N2 -0.16(18) . . . . ? Pd1 N1 S1 N2 -171.31(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.584 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.114