Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Andy Hor' 'Han Vinh Huynh' 'Lip Lin Koh' 'Swee Kuan Yen' _publ_contact_author_name 'Andy Hor' _publ_contact_author_address ; Department of Chemistry National University of Singapore 3 Science Drive 3 Singapore 117543 SINGAPORE ; _publ_contact_author_email ANDYHOR@NUS.EDU.SG _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Pd(II) complexes with mixed benzothiazolin-2-ylidene and phosphine ligands and their catalytic activites toward C-C coupling reactions ; data_5355a _database_code_depnum_ccdc_archive 'CCDC 658815' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32.50 H26.50 Br2 Cl1.50 N P Pd S' _chemical_formula_weight 813.47 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 37.007(3) _cell_length_b 9.2211(7) _cell_length_c 19.3966(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.757(2) _cell_angle_gamma 90.00 _cell_volume 6229.3(8) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2306 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.54 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3208 _exptl_absorpt_coefficient_mu 3.433 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.4689 _exptl_absorpt_correction_T_max 0.7475 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _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 21471 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7134 _reflns_number_gt 5182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+6.6320P] 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 7134 _refine_ls_number_parameters 367 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _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 0.622313(13) 0.39715(5) 0.58424(2) 0.02065(13) Uani 1 1 d . . . Br1 Br 0.65804(2) 0.62336(7) 0.62721(4) 0.03805(19) Uani 1 1 d . . . Br2 Br 0.569058(19) 0.48114(7) 0.62401(4) 0.03451(19) Uani 1 1 d . . . P1 P 0.67090(4) 0.32802(17) 0.54484(8) 0.0215(3) Uani 1 1 d . . . S1 S 0.55212(5) 0.24738(17) 0.46355(9) 0.0282(4) Uani 1 1 d . . . N1 N 0.59330(13) 0.0872(5) 0.5645(3) 0.0207(10) Uani 1 1 d . . . C1 C 0.59080(16) 0.2238(6) 0.5422(3) 0.0223(12) Uani 1 1 d . . . C2 C 0.56567(16) -0.0073(6) 0.5191(3) 0.0221(12) Uani 1 1 d . . . C3 C 0.56293(18) -0.1559(7) 0.5283(4) 0.0291(14) Uani 1 1 d . . . H3 H 0.5806 -0.2050 0.5680 0.035 Uiso 1 1 calc R . . C4 C 0.53362(19) -0.2279(7) 0.4776(4) 0.0343(15) Uani 1 1 d . . . H4 H 0.5312 -0.3286 0.4822 0.041 Uiso 1 1 calc R . . C5 C 0.50705(19) -0.1549(8) 0.4188(4) 0.0362(16) Uani 1 1 d . . . H5 H 0.4869 -0.2072 0.3854 0.043 Uiso 1 1 calc R . . C6 C 0.50995(18) -0.0083(7) 0.4091(3) 0.0312(15) Uani 1 1 d . . . H6 H 0.4924 0.0405 0.3693 0.037 Uiso 1 1 calc R . . C7 C 0.53992(17) 0.0652(6) 0.4605(3) 0.0229(13) Uani 1 1 d . . . C8 C 0.62256(16) 0.0360(7) 0.6321(3) 0.0237(13) Uani 1 1 d . . . H8A H 0.6426 0.1100 0.6497 0.028 Uiso 1 1 calc R . . H8B H 0.6346 -0.0521 0.6216 0.028 Uiso 1 1 calc R . . C9 C 0.60553(16) 0.0040(7) 0.6915(3) 0.0240(13) Uani 1 1 d . . . C10 C 0.60806(19) -0.1328(7) 0.7219(4) 0.0310(15) Uani 1 1 d . . . H10 H 0.6203 -0.2079 0.7056 0.037 Uiso 1 1 calc R . . C11 C 0.5925(2) -0.1589(8) 0.7762(4) 0.0447(19) Uani 1 1 d . . . H11 H 0.5949 -0.2512 0.7978 0.054 Uiso 1 1 calc R . . C12 C 0.5737(2) -0.0510(9) 0.7985(4) 0.0411(17) Uani 1 1 d . . . H12 H 0.5627 -0.0701 0.8346 0.049 Uiso 1 1 calc R . . C13 C 0.5708(2) 0.0850(8) 0.7686(4) 0.0370(16) Uani 1 1 d . . . H13 H 0.5579 0.1588 0.7842 0.044 Uiso 1 1 calc R . . C14 C 0.58691(18) 0.1132(7) 0.7155(3) 0.0288(14) Uani 1 1 d . . . H14 H 0.5853 0.2069 0.6956 0.035 Uiso 1 1 calc R . . C1A C 0.71736(17) 0.3824(7) 0.6094(3) 0.0285(14) Uani 1 1 d . . . C2A C 0.74340(19) 0.4642(8) 0.5889(4) 0.0396(17) Uani 1 1 d . . . H2A H 0.7376 0.4944 0.5401 0.048 Uiso 1 1 calc R . . C3A C 0.7778(2) 0.5006(12) 0.6410(6) 0.075(3) Uani 1 1 d . . . H3A H 0.7959 0.5554 0.6279 0.090 Uiso 1 1 calc R . . C4A C 0.7859(2) 0.4564(13) 0.7136(6) 0.079(4) Uani 1 1 d . . . H4A H 0.8092 0.4838 0.7493 0.094 Uiso 1 1 calc R . . C5A C 0.7609(3) 0.3758(11) 0.7329(5) 0.064(3) Uani 1 1 d . . . H5A H 0.7669 0.3450 0.7817 0.077 Uiso 1 1 calc R . . C6A C 0.7260(2) 0.3374(9) 0.6809(4) 0.0428(18) Uani 1 1 d . . . H6A H 0.7083 0.2809 0.6945 0.051 Uiso 1 1 calc R . . C1B C 0.66540(17) 0.4071(6) 0.4559(3) 0.0240(13) Uani 1 1 d . . . C2B C 0.6875(2) 0.3573(8) 0.4149(4) 0.0353(16) Uani 1 1 d . . . H2B H 0.7065 0.2868 0.4346 0.042 Uiso 1 1 calc R . . C3B C 0.6815(2) 0.4107(8) 0.3463(4) 0.0407(18) Uani 1 1 d . . . H3B H 0.6964 0.3759 0.3189 0.049 Uiso 1 1 calc R . . C4B C 0.6539(2) 0.5155(8) 0.3168(4) 0.0460(19) Uani 1 1 d . . . H4B H 0.6505 0.5537 0.2701 0.055 Uiso 1 1 calc R . . C5B C 0.6315(2) 0.5639(9) 0.3558(4) 0.048(2) Uani 1 1 d . . . H5B H 0.6120 0.6326 0.3352 0.058 Uiso 1 1 calc R . . C6B C 0.6376(2) 0.5107(7) 0.4260(4) 0.0354(16) Uani 1 1 d . . . H6B H 0.6227 0.5457 0.4532 0.042 Uiso 1 1 calc R . . C1C C 0.67723(18) 0.1362(6) 0.5293(3) 0.0241(13) Uani 1 1 d . . . C2C C 0.70951(19) 0.0567(7) 0.5707(4) 0.0310(15) Uani 1 1 d . . . H2C H 0.7290 0.1021 0.6088 0.037 Uiso 1 1 calc R . . C3C C 0.7128(2) -0.0862(8) 0.5558(4) 0.0449(19) Uani 1 1 d . . . H3C H 0.7347 -0.1382 0.5838 0.054 Uiso 1 1 calc R . . C4C C 0.6847(2) -0.1555(8) 0.5007(4) 0.0454(19) Uani 1 1 d . . . H4C H 0.6873 -0.2540 0.4909 0.054 Uiso 1 1 calc R . . C5C C 0.6523(2) -0.0789(8) 0.4597(4) 0.0425(18) Uani 1 1 d . . . H5C H 0.6326 -0.1258 0.4225 0.051 Uiso 1 1 calc R . . C6C C 0.64902(19) 0.0651(7) 0.4737(4) 0.0318(15) Uani 1 1 d . . . H6C H 0.6272 0.1168 0.4450 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.5000 0.2937(5) 0.2500 0.131(2) Uani 1 2 d SD . . Cl2 Cl 0.52747(12) 0.5561(4) 0.32209(19) 0.1192(13) Uani 1 1 d D . . C1S C 0.5098(6) 0.4706(15) 0.2377(9) 0.069(5) Uani 0.50 1 d PD . -1 H1S H 0.5307 0.4706 0.2167 0.082 Uiso 0.50 1 calc PR . -1 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 0.0239(2) 0.0190(2) 0.0207(2) -0.00023(18) 0.00966(18) -0.00102(18) Br1 0.0416(4) 0.0272(4) 0.0502(5) -0.0099(3) 0.0219(3) -0.0058(3) Br2 0.0370(4) 0.0280(4) 0.0465(4) -0.0005(3) 0.0246(3) 0.0019(3) P1 0.0234(8) 0.0238(8) 0.0176(7) -0.0004(6) 0.0075(6) -0.0005(6) S1 0.0299(9) 0.0268(8) 0.0243(8) 0.0042(6) 0.0044(7) -0.0009(7) N1 0.022(3) 0.022(3) 0.020(2) 0.003(2) 0.010(2) -0.003(2) C1 0.022(3) 0.026(3) 0.020(3) 0.003(2) 0.009(2) 0.001(2) C2 0.021(3) 0.026(3) 0.020(3) -0.002(2) 0.008(2) -0.002(2) C3 0.031(4) 0.025(3) 0.033(4) -0.001(3) 0.012(3) 0.001(3) C4 0.039(4) 0.029(3) 0.035(4) 0.000(3) 0.012(3) -0.003(3) C5 0.033(4) 0.037(4) 0.035(4) -0.007(3) 0.006(3) -0.013(3) C6 0.022(3) 0.046(4) 0.025(3) 0.000(3) 0.007(3) -0.002(3) C7 0.024(3) 0.023(3) 0.021(3) 0.000(2) 0.008(2) -0.002(2) C8 0.019(3) 0.026(3) 0.023(3) 0.000(2) 0.003(2) 0.002(2) C9 0.019(3) 0.030(3) 0.019(3) -0.001(2) 0.001(2) -0.002(3) C10 0.037(4) 0.024(3) 0.032(4) 0.009(3) 0.012(3) 0.012(3) C11 0.059(5) 0.044(4) 0.039(4) 0.023(4) 0.026(4) 0.010(4) C12 0.047(4) 0.053(5) 0.030(4) 0.005(3) 0.021(3) 0.002(4) C13 0.045(4) 0.036(4) 0.029(4) -0.006(3) 0.010(3) 0.006(3) C14 0.036(4) 0.024(3) 0.025(3) 0.002(3) 0.009(3) 0.000(3) C1A 0.022(3) 0.035(4) 0.026(3) -0.010(3) 0.005(3) 0.001(3) C2A 0.026(4) 0.048(4) 0.044(4) -0.015(4) 0.013(3) -0.011(3) C3A 0.036(5) 0.105(9) 0.084(8) -0.046(6) 0.021(5) -0.022(5) C4A 0.031(5) 0.113(9) 0.066(7) -0.053(6) -0.018(4) 0.004(5) C5A 0.053(6) 0.091(8) 0.037(5) -0.020(5) 0.000(4) 0.013(5) C6A 0.044(4) 0.051(5) 0.027(4) -0.002(3) 0.003(3) 0.002(4) C1B 0.023(3) 0.024(3) 0.025(3) 0.000(2) 0.007(2) -0.008(3) C2B 0.037(4) 0.038(4) 0.036(4) 0.005(3) 0.018(3) 0.007(3) C3B 0.045(4) 0.054(5) 0.027(4) 0.000(3) 0.017(3) -0.002(4) C4B 0.066(5) 0.043(5) 0.031(4) 0.009(3) 0.018(4) -0.001(4) C5B 0.064(5) 0.041(4) 0.034(4) 0.011(3) 0.009(4) 0.014(4) C6B 0.042(4) 0.037(4) 0.028(4) 0.005(3) 0.012(3) 0.011(3) C1C 0.031(3) 0.022(3) 0.023(3) 0.003(2) 0.014(3) -0.002(3) C2C 0.032(4) 0.028(3) 0.033(4) 0.003(3) 0.012(3) 0.003(3) C3C 0.048(5) 0.034(4) 0.054(5) 0.017(4) 0.019(4) 0.018(4) C4C 0.061(5) 0.022(4) 0.060(5) -0.001(3) 0.029(4) 0.001(4) C5C 0.050(5) 0.034(4) 0.044(4) -0.014(3) 0.017(4) -0.010(3) C6C 0.033(4) 0.035(4) 0.030(4) 0.002(3) 0.015(3) 0.003(3) Cl1 0.169(5) 0.050(2) 0.132(4) 0.000 -0.005(4) 0.000 Cl2 0.168(4) 0.094(2) 0.093(2) -0.0298(19) 0.041(2) -0.061(2) C1S 0.088(16) 0.057(11) 0.078(15) -0.015(11) 0.052(11) -0.008(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 Pd1 C1 1.984(6) . ? Pd1 P1 2.2698(15) . ? Pd1 Br1 2.4595(8) . ? Pd1 Br2 2.4712(8) . ? P1 C1B 1.819(6) . ? P1 C1A 1.822(6) . ? P1 C1C 1.823(6) . ? S1 C1 1.716(6) . ? S1 C7 1.736(6) . ? N1 C1 1.325(7) . ? N1 C2 1.404(7) . ? N1 C8 1.468(7) . ? C2 C7 1.383(8) . ? C2 C3 1.391(8) . ? C3 C4 1.365(9) . ? C4 C5 1.400(9) . ? C5 C6 1.374(9) . ? C6 C7 1.391(8) . ? C8 C9 1.518(8) . ? C9 C10 1.382(8) . ? C9 C14 1.387(8) . ? C10 C11 1.381(9) . ? C11 C12 1.366(10) . ? C12 C13 1.371(10) . ? C13 C14 1.376(9) . ? C1A C6A 1.379(9) . ? C1A C2A 1.383(9) . ? C2A C3A 1.372(10) . ? C3A C4A 1.398(14) . ? C4A C5A 1.335(14) . ? C5A C6A 1.388(11) . ? C1B C6B 1.380(9) . ? C1B C2B 1.397(9) . ? C2B C3B 1.365(9) . ? C3B C4B 1.382(10) . ? C4B C5B 1.376(11) . ? C5B C6B 1.391(9) . ? C1C C6C 1.387(9) . ? C1C C2C 1.400(9) . ? C2C C3C 1.363(10) . ? C3C C4C 1.372(11) . ? C4C C5C 1.387(11) . ? C5C C6C 1.369(9) . ? Cl1 C1S 1.704(13) . ? Cl1 C1S 1.704(13) 2_655 ? Cl2 C1S 1.67(2) 2_655 ? Cl2 C1S 1.733(15) . ? C1S Cl2 1.67(2) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 P1 93.31(16) . . ? C1 Pd1 Br1 175.16(17) . . ? P1 Pd1 Br1 87.48(5) . . ? C1 Pd1 Br2 87.76(16) . . ? P1 Pd1 Br2 177.71(5) . . ? Br1 Pd1 Br2 91.29(3) . . ? C1B P1 C1A 108.5(3) . . ? C1B P1 C1C 102.2(3) . . ? C1A P1 C1C 103.7(3) . . ? C1B P1 Pd1 111.0(2) . . ? C1A P1 Pd1 111.3(2) . . ? C1C P1 Pd1 119.27(19) . . ? C1 S1 C7 92.1(3) . . ? C1 N1 C2 115.4(5) . . ? C1 N1 C8 123.1(5) . . ? C2 N1 C8 121.4(5) . . ? N1 C1 S1 110.8(4) . . ? N1 C1 Pd1 131.7(4) . . ? S1 C1 Pd1 117.5(3) . . ? C7 C2 C3 121.5(6) . . ? C7 C2 N1 111.6(5) . . ? C3 C2 N1 126.9(5) . . ? C4 C3 C2 117.4(6) . . ? C3 C4 C5 121.5(6) . . ? C6 C5 C4 121.2(6) . . ? C5 C6 C7 117.5(6) . . ? C2 C7 C6 121.0(6) . . ? C2 C7 S1 109.9(4) . . ? C6 C7 S1 129.1(5) . . ? N1 C8 C9 111.7(5) . . ? C10 C9 C14 119.3(6) . . ? C10 C9 C8 121.0(6) . . ? C14 C9 C8 119.7(5) . . ? C11 C10 C9 119.9(6) . . ? C12 C11 C10 120.2(7) . . ? C11 C12 C13 120.5(6) . . ? C12 C13 C14 119.9(6) . . ? C13 C14 C9 120.2(6) . . ? C6A C1A C2A 120.4(6) . . ? C6A C1A P1 116.9(5) . . ? C2A C1A P1 122.7(5) . . ? C3A C2A C1A 119.0(8) . . ? C2A C3A C4A 120.0(9) . . ? C5A C4A C3A 120.8(8) . . ? C4A C5A C6A 120.0(9) . . ? C1A C6A C5A 119.8(8) . . ? C6B C1B C2B 118.9(6) . . ? C6B C1B P1 120.4(5) . . ? C2B C1B P1 120.6(5) . . ? C3B C2B C1B 120.3(6) . . ? C2B C3B C4B 120.6(7) . . ? C5B C4B C3B 119.9(7) . . ? C4B C5B C6B 119.6(7) . . ? C1B C6B C5B 120.6(6) . . ? C6C C1C C2C 118.1(6) . . ? C6C C1C P1 118.9(5) . . ? C2C C1C P1 123.1(5) . . ? C3C C2C C1C 120.3(7) . . ? C2C C3C C4C 121.1(7) . . ? C3C C4C C5C 119.4(7) . . ? C6C C5C C4C 119.8(7) . . ? C5C C6C C1C 121.3(7) . . ? C1S Cl1 C1S 33.8(11) . 2_655 ? C1S Cl2 C1S 33.8(10) 2_655 . ? Cl2 C1S Cl1 112.6(10) 2_655 . ? Cl2 C1S Cl2 113.6(9) 2_655 . ? Cl1 C1S Cl2 109.5(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.228 _refine_diff_density_min -1.032 _refine_diff_density_rms 0.165 # Attachment 'complex_4.cif' data_5380 _database_code_depnum_ccdc_archive 'CCDC 658816' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Br2 N P Pd S' _chemical_formula_weight 705.75 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6363(7) _cell_length_b 15.0349(11) _cell_length_c 20.3556(15) _cell_angle_alpha 68.8730(10) _cell_angle_beta 79.833(2) _cell_angle_gamma 88.787(2) _cell_volume 2704.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5146 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 23.43 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 3.795 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.3956 _exptl_absorpt_correction_T_max 0.8043 _exptl_absorpt_process_details ? _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 'CCD area detector' _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 32639 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.50 _reflns_number_total 12414 _reflns_number_gt 8638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12414 _refine_ls_number_parameters 615 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.002 _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 0.19013(3) 0.10646(2) 0.251222(17) 0.02657(8) Uani 1 1 d . . . Pd2 Pd 0.71836(3) 0.54323(2) 0.308300(18) 0.02754(9) Uani 1 1 d . . . Br1 Br 0.13868(5) 0.27729(3) 0.20368(3) 0.04059(12) Uani 1 1 d . . . Br2 Br 0.10553(5) 0.09564(4) 0.37635(3) 0.04446(13) Uani 1 1 d . . . Br3 Br 0.77376(6) 0.70404(3) 0.21557(3) 0.05041(15) Uani 1 1 d . . . Br4 Br 0.77159(5) 0.59447(4) 0.40470(3) 0.04658(14) Uani 1 1 d . . . S1 S 0.39548(11) -0.06774(8) 0.29976(6) 0.0325(2) Uani 1 1 d . . . S2 S 0.50203(11) 0.38766(8) 0.42888(6) 0.0339(3) Uani 1 1 d . . . N1 N 0.1354(4) -0.1045(3) 0.3230(2) 0.0352(9) Uani 1 1 d . . . N2 N 0.7488(3) 0.3401(2) 0.39752(19) 0.0279(8) Uani 1 1 d . . . P1 P 0.26799(11) 0.11631(8) 0.13685(6) 0.0280(2) Uani 1 1 d . . . P2 P 0.63892(11) 0.48915(7) 0.22962(6) 0.0268(2) Uani 1 1 d . . . C1 C 0.2285(4) -0.0310(3) 0.2927(2) 0.0277(9) Uani 1 1 d . . . C2 C 0.1937(5) -0.1942(3) 0.3518(2) 0.0337(10) Uani 1 1 d . . . C3 C 0.1205(6) -0.2816(3) 0.3866(3) 0.0491(13) Uani 1 1 d . . . H3 H 0.0229 -0.2868 0.3920 0.059 Uiso 1 1 calc R . . C4 C 0.1982(6) -0.3609(3) 0.4132(3) 0.0507(14) Uani 1 1 d . . . H4 H 0.1520 -0.4206 0.4363 0.061 Uiso 1 1 calc R . . C5 C 0.3432(7) -0.3530(3) 0.4062(3) 0.0507(14) Uani 1 1 d . . . H5 H 0.3924 -0.4071 0.4262 0.061 Uiso 1 1 calc R . . C6 C 0.4156(6) -0.2667(3) 0.3702(3) 0.0415(12) Uani 1 1 d . . . H6 H 0.5135 -0.2620 0.3637 0.050 Uiso 1 1 calc R . . C7 C 0.3389(5) -0.1868(3) 0.3440(2) 0.0326(10) Uani 1 1 d . . . C8 C -0.0188(5) -0.0938(4) 0.3292(3) 0.0460(13) Uani 1 1 d . . . H8A H -0.0660 -0.1398 0.3745 0.055 Uiso 1 1 calc R . . H8B H -0.0403 -0.0305 0.3292 0.055 Uiso 1 1 calc R . . C9 C -0.0737(5) -0.1078(4) 0.2703(3) 0.0554(14) Uani 1 1 d . . . H9A H -0.0592 -0.1726 0.2720 0.066 Uiso 1 1 calc R . . H9B H -0.0236 -0.0644 0.2246 0.066 Uiso 1 1 calc R . . C10 C -0.2340(5) -0.0887(4) 0.2779(4) 0.0668(18) Uani 1 1 d . . . H10A H -0.2817 -0.1281 0.3248 0.100 Uiso 1 1 calc R . . H10B H -0.2722 -0.1036 0.2425 0.100 Uiso 1 1 calc R . . H10C H -0.2469 -0.0227 0.2712 0.100 Uiso 1 1 calc R . . C11 C 0.6706(4) 0.4154(3) 0.3815(2) 0.0285(9) Uani 1 1 d . . . C12 C 0.6785(5) 0.2552(3) 0.4459(2) 0.0314(10) Uani 1 1 d . . . C13 C 0.7325(5) 0.1647(3) 0.4694(3) 0.0397(11) Uani 1 1 d . . . H13 H 0.8273 0.1552 0.4560 0.048 Uiso 1 1 calc R . . C14 C 0.6408(7) 0.0903(3) 0.5131(3) 0.0560(15) Uani 1 1 d . . . H14 H 0.6750 0.0294 0.5298 0.067 Uiso 1 1 calc R . . C15 C 0.4986(6) 0.1024(4) 0.5334(3) 0.0539(15) Uani 1 1 d . . . H15 H 0.4391 0.0495 0.5617 0.065 Uiso 1 1 calc R . . C16 C 0.4442(6) 0.1919(4) 0.5120(3) 0.0467(13) Uani 1 1 d . . . H16 H 0.3498 0.2011 0.5266 0.056 Uiso 1 1 calc R . . C17 C 0.5371(4) 0.2677(3) 0.4676(2) 0.0332(10) Uani 1 1 d . . . C18 C 0.9017(4) 0.3446(3) 0.3689(2) 0.0347(10) Uani 1 1 d . . . H18A H 0.9245 0.3995 0.3247 0.042 Uiso 1 1 calc R . . H18B H 0.9257 0.2877 0.3582 0.042 Uiso 1 1 calc R . . C19 C 0.9879(5) 0.3522(4) 0.4222(3) 0.0439(12) Uani 1 1 d . . . H19A H 0.9625 0.4085 0.4334 0.053 Uiso 1 1 calc R . . H19B H 0.9656 0.2969 0.4661 0.053 Uiso 1 1 calc R . . C20 C 1.1447(5) 0.3582(4) 0.3935(3) 0.0597(16) Uani 1 1 d . . . H20A H 1.1709 0.3014 0.3842 0.090 Uiso 1 1 calc R . . H20B H 1.1956 0.3645 0.4282 0.090 Uiso 1 1 calc R . . H20C H 1.1670 0.4128 0.3499 0.090 Uiso 1 1 calc R . . C1A C 0.3555(5) 0.0128(3) 0.1262(2) 0.0316(10) Uani 1 1 d . . . C2A C 0.5008(5) 0.0069(3) 0.1197(2) 0.0400(11) Uani 1 1 d . . . H2A H 0.5567 0.0599 0.1138 0.048 Uiso 1 1 calc R . . C3A C 0.5626(6) -0.0780(4) 0.1221(3) 0.0497(13) Uani 1 1 d . . . H3A H 0.6596 -0.0826 0.1199 0.060 Uiso 1 1 calc R . . C4A C 0.4834(7) -0.1540(4) 0.1277(3) 0.0586(16) Uani 1 1 d . . . H4A H 0.5264 -0.2104 0.1289 0.070 Uiso 1 1 calc R . . C5A C 0.3399(7) -0.1493(4) 0.1316(3) 0.0546(14) Uani 1 1 d . . . H5A H 0.2863 -0.2017 0.1345 0.066 Uiso 1 1 calc R . . C6A C 0.2753(5) -0.0656(3) 0.1310(3) 0.0429(12) Uani 1 1 d . . . H6A H 0.1781 -0.0621 0.1339 0.052 Uiso 1 1 calc R . . C1B C 0.4046(5) 0.2100(3) 0.0889(2) 0.0329(10) Uani 1 1 d . . . C2B C 0.4736(5) 0.2495(3) 0.1260(2) 0.0381(11) Uani 1 1 d . . . H2B H 0.4453 0.2317 0.1753 0.046 Uiso 1 1 calc R . . C3B C 0.5851(5) 0.3157(4) 0.0907(3) 0.0541(14) Uani 1 1 d . . . H3B H 0.6323 0.3415 0.1163 0.065 Uiso 1 1 calc R . . C4B C 0.6259(5) 0.3434(4) 0.0172(3) 0.0486(13) Uani 1 1 d . . . H4B H 0.6983 0.3897 -0.0070 0.058 Uiso 1 1 calc R . . C5B C 0.5598(6) 0.3027(4) -0.0195(3) 0.0534(14) Uani 1 1 d . . . H5B H 0.5898 0.3193 -0.0685 0.064 Uiso 1 1 calc R . . C6B C 0.4492(6) 0.2374(4) 0.0155(3) 0.0534(14) Uani 1 1 d . . . H6B H 0.4035 0.2112 -0.0103 0.064 Uiso 1 1 calc R . . C1C C 0.1249(5) 0.1303(3) 0.0863(2) 0.0330(10) Uani 1 1 d . . . C2C C 0.1445(6) 0.1213(4) 0.0206(3) 0.0571(15) Uani 1 1 d . . . H2C H 0.2335 0.1092 0.0001 0.069 Uiso 1 1 calc R . . C3C C 0.0325(7) 0.1300(5) -0.0152(3) 0.0727(19) Uani 1 1 d . . . H3C H 0.0475 0.1256 -0.0603 0.087 Uiso 1 1 calc R . . C4C C -0.0998(6) 0.1449(4) 0.0151(3) 0.0633(16) Uani 1 1 d . . . H4C H -0.1749 0.1503 -0.0090 0.076 Uiso 1 1 calc R . . C5C C -0.1203(6) 0.1518(4) 0.0807(3) 0.0595(16) Uani 1 1 d . . . H5C H -0.2103 0.1613 0.1018 0.071 Uiso 1 1 calc R . . C6C C -0.0098(5) 0.1449(4) 0.1162(3) 0.0462(12) Uani 1 1 d . . . H6C H -0.0258 0.1502 0.1611 0.055 Uiso 1 1 calc R . . C1D C 0.6278(4) 0.3593(3) 0.2556(2) 0.0275(9) Uani 1 1 d . . . C2D C 0.7487(4) 0.3123(3) 0.2431(2) 0.0315(10) Uani 1 1 d . . . H2D H 0.8321 0.3470 0.2175 0.038 Uiso 1 1 calc R . . C3D C 0.7457(5) 0.2133(3) 0.2687(3) 0.0427(12) Uani 1 1 d . . . H3D H 0.8277 0.1818 0.2612 0.051 Uiso 1 1 calc R . . C4D C 0.6217(6) 0.1614(3) 0.3051(3) 0.0453(12) Uani 1 1 d . . . H4D H 0.6195 0.0951 0.3211 0.054 Uiso 1 1 calc R . . C5D C 0.5017(5) 0.2076(3) 0.3177(2) 0.0379(11) Uani 1 1 d . . . H5D H 0.4182 0.1724 0.3426 0.045 Uiso 1 1 calc R . . C6D C 0.5037(4) 0.3051(3) 0.2940(2) 0.0318(10) Uani 1 1 d . . . H6D H 0.4218 0.3357 0.3035 0.038 Uiso 1 1 calc R . . C1E C 0.4592(4) 0.5258(3) 0.2218(2) 0.0267(9) Uani 1 1 d . . . C2E C 0.4071(4) 0.5950(3) 0.2482(2) 0.0343(10) Uani 1 1 d . . . H2E H 0.4643 0.6222 0.2690 0.041 Uiso 1 1 calc R . . C3E C 0.2712(5) 0.6243(3) 0.2440(3) 0.0433(12) Uani 1 1 d . . . H3E H 0.2375 0.6707 0.2623 0.052 Uiso 1 1 calc R . . C4E C 0.1860(5) 0.5858(3) 0.2135(3) 0.0423(12) Uani 1 1 d . . . H4E H 0.0948 0.6063 0.2104 0.051 Uiso 1 1 calc R . . C5E C 0.2362(5) 0.5154(3) 0.1867(2) 0.0356(11) Uani 1 1 d . . . H5E H 0.1787 0.4887 0.1658 0.043 Uiso 1 1 calc R . . C6E C 0.3714(4) 0.4857(3) 0.1915(2) 0.0323(10) Uani 1 1 d . . . H6E H 0.4044 0.4382 0.1743 0.039 Uiso 1 1 calc R . . C1F C 0.7439(4) 0.5305(3) 0.1398(2) 0.0299(10) Uani 1 1 d . . . C2F C 0.6875(5) 0.5456(4) 0.0793(3) 0.0466(13) Uani 1 1 d . . . H2F H 0.5916 0.5325 0.0841 0.056 Uiso 1 1 calc R . . C3F C 0.7696(6) 0.5797(4) 0.0119(3) 0.0540(14) Uani 1 1 d . . . H3F H 0.7286 0.5894 -0.0280 0.065 Uiso 1 1 calc R . . C4F C 0.9099(6) 0.5994(4) 0.0034(3) 0.0527(14) Uani 1 1 d . . . H4F H 0.9654 0.6226 -0.0421 0.063 Uiso 1 1 calc R . . C5F C 0.9684(6) 0.5843(5) 0.0633(3) 0.0655(17) Uani 1 1 d . . . H5F H 1.0644 0.5975 0.0581 0.079 Uiso 1 1 calc R . . C6F C 0.8866(5) 0.5499(4) 0.1309(3) 0.0527(14) Uani 1 1 d . . . H6F H 0.9282 0.5396 0.1707 0.063 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 0.02210(16) 0.02694(17) 0.03037(18) -0.01108(14) -0.00269(13) 0.00258(13) Pd2 0.02044(16) 0.02625(17) 0.0358(2) -0.00956(14) -0.00837(14) 0.00021(13) Br1 0.0371(3) 0.0301(2) 0.0524(3) -0.0150(2) -0.0031(2) 0.0058(2) Br2 0.0453(3) 0.0508(3) 0.0369(3) -0.0197(2) 0.0012(2) 0.0060(2) Br3 0.0561(3) 0.0308(3) 0.0576(3) -0.0055(2) -0.0148(3) -0.0053(2) Br4 0.0479(3) 0.0478(3) 0.0519(3) -0.0231(3) -0.0177(2) -0.0048(2) S1 0.0223(5) 0.0320(6) 0.0409(7) -0.0093(5) -0.0085(5) 0.0020(4) S2 0.0207(5) 0.0373(6) 0.0414(7) -0.0127(5) -0.0033(5) 0.0004(4) N1 0.0225(18) 0.035(2) 0.045(2) -0.0129(18) -0.0019(17) -0.0008(16) N2 0.0211(17) 0.0304(19) 0.032(2) -0.0097(16) -0.0079(15) 0.0031(15) P1 0.0262(6) 0.0269(6) 0.0307(6) -0.0106(5) -0.0044(5) 0.0037(4) P2 0.0193(5) 0.0262(5) 0.0330(6) -0.0082(5) -0.0059(5) 0.0008(4) C1 0.023(2) 0.031(2) 0.026(2) -0.0094(18) 0.0022(17) 0.0011(17) C2 0.036(2) 0.029(2) 0.034(3) -0.011(2) -0.003(2) -0.0001(19) C3 0.052(3) 0.038(3) 0.050(3) -0.013(2) 0.005(3) -0.010(2) C4 0.076(4) 0.030(3) 0.041(3) -0.010(2) -0.003(3) -0.005(3) C5 0.084(4) 0.032(3) 0.041(3) -0.015(2) -0.021(3) 0.017(3) C6 0.053(3) 0.034(3) 0.043(3) -0.016(2) -0.018(2) 0.015(2) C7 0.037(2) 0.032(2) 0.030(2) -0.013(2) -0.006(2) 0.0035(19) C8 0.025(2) 0.043(3) 0.066(4) -0.018(3) -0.001(2) -0.003(2) C9 0.038(3) 0.065(4) 0.068(4) -0.032(3) -0.005(3) 0.001(3) C10 0.029(3) 0.081(4) 0.111(5) -0.055(4) -0.025(3) 0.010(3) C11 0.020(2) 0.031(2) 0.034(2) -0.0102(19) -0.0070(18) -0.0028(17) C12 0.033(2) 0.033(2) 0.028(2) -0.0085(19) -0.0111(19) 0.0007(19) C13 0.044(3) 0.035(3) 0.046(3) -0.016(2) -0.018(2) 0.006(2) C14 0.091(5) 0.029(3) 0.045(3) -0.002(2) -0.028(3) 0.004(3) C15 0.070(4) 0.040(3) 0.042(3) -0.001(2) -0.012(3) -0.022(3) C16 0.047(3) 0.049(3) 0.037(3) -0.005(2) -0.008(2) -0.014(2) C17 0.028(2) 0.037(2) 0.032(2) -0.009(2) -0.0067(19) -0.0042(19) C18 0.021(2) 0.040(3) 0.039(3) -0.010(2) -0.0052(19) 0.0063(19) C19 0.026(2) 0.063(3) 0.046(3) -0.021(3) -0.011(2) 0.006(2) C20 0.021(2) 0.072(4) 0.082(4) -0.022(3) -0.011(3) 0.002(2) C1A 0.031(2) 0.037(2) 0.030(2) -0.016(2) -0.0057(19) 0.0081(19) C2A 0.037(3) 0.046(3) 0.039(3) -0.020(2) -0.002(2) 0.008(2) C3A 0.045(3) 0.066(4) 0.042(3) -0.026(3) -0.008(2) 0.026(3) C4A 0.087(5) 0.051(3) 0.043(3) -0.026(3) -0.013(3) 0.034(3) C5A 0.074(4) 0.035(3) 0.060(4) -0.022(3) -0.016(3) 0.010(3) C6A 0.041(3) 0.041(3) 0.052(3) -0.023(2) -0.010(2) 0.007(2) C1B 0.035(2) 0.027(2) 0.036(3) -0.0114(19) -0.002(2) 0.0014(19) C2B 0.030(2) 0.055(3) 0.031(3) -0.018(2) -0.004(2) 0.000(2) C3B 0.029(3) 0.077(4) 0.061(4) -0.029(3) -0.010(3) -0.005(3) C4B 0.032(3) 0.043(3) 0.060(4) -0.011(3) 0.005(2) -0.008(2) C5B 0.066(4) 0.050(3) 0.036(3) -0.017(3) 0.015(3) -0.012(3) C6B 0.075(4) 0.048(3) 0.035(3) -0.017(2) 0.000(3) -0.021(3) C1C 0.032(2) 0.031(2) 0.036(3) -0.009(2) -0.012(2) 0.0044(19) C2C 0.038(3) 0.090(4) 0.047(3) -0.026(3) -0.013(3) 0.005(3) C3C 0.068(4) 0.113(5) 0.049(4) -0.036(4) -0.026(3) 0.006(4) C4C 0.048(4) 0.074(4) 0.077(5) -0.029(4) -0.034(3) 0.010(3) C5C 0.037(3) 0.067(4) 0.085(5) -0.035(3) -0.023(3) 0.006(3) C6C 0.036(3) 0.056(3) 0.052(3) -0.025(3) -0.009(2) 0.005(2) C1D 0.024(2) 0.030(2) 0.030(2) -0.0103(18) -0.0099(18) 0.0013(17) C2D 0.027(2) 0.038(2) 0.030(2) -0.012(2) -0.0061(19) 0.0057(19) C3D 0.045(3) 0.042(3) 0.042(3) -0.017(2) -0.006(2) 0.014(2) C4D 0.066(4) 0.028(2) 0.041(3) -0.011(2) -0.013(3) 0.004(2) C5D 0.040(3) 0.033(2) 0.037(3) -0.010(2) -0.006(2) -0.008(2) C6D 0.022(2) 0.040(3) 0.034(2) -0.013(2) -0.0069(19) 0.0064(19) C1E 0.0166(19) 0.027(2) 0.034(2) -0.0073(18) -0.0065(17) 0.0050(16) C2E 0.029(2) 0.038(3) 0.039(3) -0.016(2) -0.011(2) 0.0016(19) C3E 0.035(3) 0.045(3) 0.056(3) -0.023(3) -0.015(2) 0.009(2) C4E 0.023(2) 0.043(3) 0.059(3) -0.014(2) -0.012(2) 0.007(2) C5E 0.029(2) 0.028(2) 0.046(3) -0.005(2) -0.016(2) -0.0010(19) C6E 0.030(2) 0.031(2) 0.033(2) -0.0076(19) -0.0058(19) -0.0012(19) C1F 0.020(2) 0.026(2) 0.040(3) -0.0087(19) -0.0023(19) -0.0015(17) C2F 0.034(3) 0.057(3) 0.038(3) -0.006(2) -0.006(2) -0.004(2) C3F 0.054(3) 0.058(3) 0.039(3) -0.004(3) -0.010(3) 0.005(3) C4F 0.054(3) 0.046(3) 0.042(3) -0.007(2) 0.012(3) 0.007(3) C5F 0.026(3) 0.093(5) 0.068(4) -0.024(4) 0.009(3) -0.011(3) C6F 0.030(3) 0.082(4) 0.047(3) -0.023(3) -0.008(2) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pd1 C1 1.986(4) . ? Pd1 P1 2.2682(12) . ? Pd1 Br1 2.4703(6) . ? Pd1 Br2 2.4804(6) . ? Pd2 C11 1.964(4) . ? Pd2 P2 2.2826(11) . ? Pd2 Br3 2.4703(6) . ? Pd2 Br4 2.4837(6) . ? S1 C1 1.703(4) . ? S1 C7 1.737(4) . ? S2 C11 1.711(4) . ? S2 C17 1.741(4) . ? N1 C1 1.328(5) . ? N1 C2 1.411(5) . ? N1 C8 1.479(5) . ? N2 C11 1.320(5) . ? N2 C12 1.397(5) . ? N2 C18 1.479(5) . ? P1 C1A 1.818(4) . ? P1 C1B 1.818(4) . ? P1 C1C 1.826(4) . ? P2 C1F 1.819(4) . ? P2 C1E 1.822(4) . ? P2 C1D 1.830(4) . ? C2 C7 1.383(6) . ? C2 C3 1.384(6) . ? C3 C4 1.384(7) . ? C4 C5 1.382(8) . ? C5 C6 1.371(7) . ? C6 C7 1.383(6) . ? C8 C9 1.475(7) . ? C9 C10 1.556(7) . ? C12 C17 1.386(6) . ? C12 C13 1.393(6) . ? C13 C14 1.368(7) . ? C14 C15 1.388(8) . ? C15 C16 1.379(7) . ? C16 C17 1.390(6) . ? C18 C19 1.513(6) . ? C19 C20 1.513(6) . ? C1A C2A 1.387(6) . ? C1A C6A 1.387(6) . ? C2A C3A 1.386(6) . ? C3A C4A 1.347(8) . ? C4A C5A 1.373(8) . ? C5A C6A 1.389(6) . ? C1B C2B 1.373(6) . ? C1B C6B 1.386(6) . ? C2B C3B 1.385(7) . ? C3B C4B 1.384(7) . ? C4B C5B 1.361(7) . ? C5B C6B 1.370(7) . ? C1C C2C 1.373(7) . ? C1C C6C 1.382(6) . ? C2C C3C 1.385(7) . ? C3C C4C 1.366(8) . ? C4C C5C 1.356(8) . ? C5C C6C 1.372(7) . ? C1D C2D 1.383(6) . ? C1D C6D 1.399(6) . ? C2D C3D 1.387(6) . ? C3D C4D 1.376(7) . ? C4D C5D 1.369(7) . ? C5D C6D 1.368(6) . ? C1E C2E 1.383(6) . ? C1E C6E 1.390(6) . ? C2E C3E 1.379(6) . ? C3E C4E 1.363(6) . ? C4E C5E 1.398(6) . ? C5E C6E 1.376(6) . ? C1F C2F 1.375(6) . ? C1F C6F 1.379(6) . ? C2F C3F 1.378(7) . ? C3F C4F 1.357(7) . ? C4F C5F 1.376(8) . ? C5F C6F 1.379(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 C1 Pd1 P1 93.62(12) . . ? C1 Pd1 Br1 178.11(12) . . ? P1 Pd1 Br1 88.26(3) . . ? C1 Pd1 Br2 86.34(12) . . ? P1 Pd1 Br2 179.88(4) . . ? Br1 Pd1 Br2 91.779(19) . . ? C11 Pd2 P2 87.83(12) . . ? C11 Pd2 Br3 178.85(11) . . ? P2 Pd2 Br3 91.40(3) . . ? C11 Pd2 Br4 87.55(12) . . ? P2 Pd2 Br4 171.93(3) . . ? Br3 Pd2 Br4 93.11(2) . . ? C1 S1 C7 93.0(2) . . ? C11 S2 C17 92.1(2) . . ? C1 N1 C2 115.1(3) . . ? C1 N1 C8 123.0(4) . . ? C2 N1 C8 121.9(4) . . ? C11 N2 C12 115.4(3) . . ? C11 N2 C18 123.0(4) . . ? C12 N2 C18 121.6(3) . . ? C1A P1 C1B 101.3(2) . . ? C1A P1 C1C 103.2(2) . . ? C1B P1 C1C 110.2(2) . . ? C1A P1 Pd1 115.94(15) . . ? C1B P1 Pd1 112.73(15) . . ? C1C P1 Pd1 112.55(15) . . ? C1F P2 C1E 107.50(19) . . ? C1F P2 C1D 103.91(19) . . ? C1E P2 C1D 104.69(18) . . ? C1F P2 Pd2 115.07(14) . . ? C1E P2 Pd2 109.58(14) . . ? C1D P2 Pd2 115.31(13) . . ? N1 C1 S1 110.7(3) . . ? N1 C1 Pd1 127.8(3) . . ? S1 C1 Pd1 121.3(2) . . ? C7 C2 C3 121.1(4) . . ? C7 C2 N1 112.1(4) . . ? C3 C2 N1 126.8(4) . . ? C4 C3 C2 117.5(5) . . ? C5 C4 C3 121.3(5) . . ? C6 C5 C4 121.0(5) . . ? C5 C6 C7 118.2(5) . . ? C2 C7 C6 120.9(4) . . ? C2 C7 S1 109.1(3) . . ? C6 C7 S1 130.0(4) . . ? C9 C8 N1 112.3(4) . . ? C8 C9 C10 109.1(4) . . ? N2 C11 S2 111.1(3) . . ? N2 C11 Pd2 129.1(3) . . ? S2 C11 Pd2 119.6(2) . . ? C17 C12 C13 120.2(4) . . ? C17 C12 N2 112.0(4) . . ? C13 C12 N2 127.7(4) . . ? C14 C13 C12 117.5(5) . . ? C13 C14 C15 122.3(5) . . ? C16 C15 C14 120.9(5) . . ? C15 C16 C17 116.9(5) . . ? C12 C17 C16 122.2(4) . . ? C12 C17 S2 109.2(3) . . ? C16 C17 S2 128.6(4) . . ? N2 C18 C19 111.0(4) . . ? C20 C19 C18 111.9(4) . . ? C2A C1A C6A 118.9(4) . . ? C2A C1A P1 121.3(4) . . ? C6A C1A P1 119.6(3) . . ? C3A C2A C1A 119.9(5) . . ? C4A C3A C2A 120.6(5) . . ? C3A C4A C5A 120.8(5) . . ? C4A C5A C6A 119.6(5) . . ? C1A C6A C5A 120.2(5) . . ? C2B C1B C6B 118.6(4) . . ? C2B C1B P1 120.0(3) . . ? C6B C1B P1 121.2(4) . . ? C1B C2B C3B 120.6(5) . . ? C4B C3B C2B 119.7(5) . . ? C5B C4B C3B 119.8(5) . . ? C4B C5B C6B 120.3(5) . . ? C5B C6B C1B 120.9(5) . . ? C2C C1C C6C 118.1(4) . . ? C2C C1C P1 122.1(4) . . ? C6C C1C P1 119.7(4) . . ? C1C C2C C3C 120.3(5) . . ? C4C C3C C2C 120.7(6) . . ? C5C C4C C3C 119.2(5) . . ? C4C C5C C6C 120.8(5) . . ? C5C C6C C1C 120.9(5) . . ? C2D C1D C6D 118.7(4) . . ? C2D C1D P2 119.2(3) . . ? C6D C1D P2 121.8(3) . . ? C1D C2D C3D 120.1(4) . . ? C4D C3D C2D 120.2(4) . . ? C5D C4D C3D 119.9(4) . . ? C6D C5D C4D 120.5(4) . . ? C5D C6D C1D 120.5(4) . . ? C2E C1E C6E 118.6(4) . . ? C2E C1E P2 118.7(3) . . ? C6E C1E P2 122.7(3) . . ? C3E C2E C1E 120.6(4) . . ? C4E C3E C2E 120.6(4) . . ? C3E C4E C5E 119.7(4) . . ? C6E C5E C4E 119.6(4) . . ? C5E C6E C1E 120.9(4) . . ? C2F C1F C6F 117.7(4) . . ? C2F C1F P2 123.2(3) . . ? C6F C1F P2 119.1(4) . . ? C1F C2F C3F 121.6(5) . . ? C4F C3F C2F 120.5(5) . . ? C3F C4F C5F 118.7(5) . . ? C4F C5F C6F 120.9(5) . . ? C1F C6F C5F 120.5(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.198 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.120 # Attachment 'complex_5.cif' data_6045 _database_code_depnum_ccdc_archive 'CCDC 658817' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H44 Br2 N P Pd S' _chemical_formula_weight 771.93 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 13.3879(8) _cell_length_b 13.6014(7) _cell_length_c 18.6842(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.5010(10) _cell_angle_gamma 90.00 _cell_volume 3278.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1489 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 18.90 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 3.138 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.5197 _exptl_absorpt_correction_T_max 0.6337 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _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 23121 _diffrn_reflns_av_R_equivalents 0.0932 _diffrn_reflns_av_sigmaI/netI 0.1137 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7523 _reflns_number_gt 3867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7523 _refine_ls_number_parameters 397 _refine_ls_number_restraints 81 _refine_ls_R_factor_all 0.1584 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.1791 _refine_ls_wR_factor_gt 0.1511 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.30471(5) 0.47853(4) 0.86708(3) 0.04575(19) Uani 1 1 d . A . S1 S 0.51062(17) 0.37873(16) 0.96123(11) 0.0599(6) Uani 1 1 d . A . P1 P 0.20167(16) 0.35976(15) 0.89872(10) 0.0475(5) Uani 1 1 d D . . Br1 Br 0.16443(8) 0.59927(7) 0.85780(6) 0.0782(3) Uani 1 1 d . . . Br2 Br 0.41897(8) 0.61079(7) 0.84293(5) 0.0730(3) Uani 1 1 d . . . N1 N 0.4532(5) 0.3385(4) 0.8251(3) 0.0485(15) Uani 1 1 d . A . C1 C 0.4233(6) 0.3906(5) 0.8763(4) 0.0447(18) Uani 1 1 d . . . C2 C 0.5444(6) 0.2825(6) 0.8510(4) 0.0529(19) Uani 1 1 d . . . C3 C 0.5864(7) 0.2151(7) 0.8116(5) 0.073(3) Uani 1 1 d . A . H3 H 0.5564 0.2035 0.7608 0.088 Uiso 1 1 calc R . . C4 C 0.6731(8) 0.1667(8) 0.8497(6) 0.090(3) Uani 1 1 d . . . H4 H 0.7042 0.1213 0.8244 0.108 Uiso 1 1 calc R A . C5 C 0.7172(9) 0.1825(8) 0.9250(7) 0.098(4) Uani 1 1 d . A . H5 H 0.7774 0.1477 0.9493 0.118 Uiso 1 1 calc R . . C6 C 0.6750(7) 0.2473(7) 0.9643(5) 0.081(3) Uani 1 1 d . . . H6 H 0.7054 0.2578 1.0152 0.097 Uiso 1 1 calc R A . C7 C 0.5872(6) 0.2966(6) 0.9276(4) 0.056(2) Uani 1 1 d . A . C8 C 0.3959(6) 0.3415(6) 0.7455(4) 0.0526(19) Uani 1 1 d . . . H8A H 0.3336 0.3818 0.7397 0.063 Uiso 1 1 calc R A . H8B H 0.3734 0.2747 0.7290 0.063 Uiso 1 1 calc R . . C9 C 0.4589(6) 0.3824(6) 0.6961(4) 0.053(2) Uani 1 1 d . A . C10 C 0.5259(8) 0.4568(8) 0.7187(5) 0.087(3) Uani 1 1 d . . . H10 H 0.5360 0.4825 0.7669 0.105 Uiso 1 1 calc R A . C11 C 0.5804(9) 0.4964(9) 0.6717(7) 0.106(4) Uani 1 1 d . A . H11 H 0.6261 0.5494 0.6875 0.127 Uiso 1 1 calc R . . C12 C 0.5669(9) 0.4579(8) 0.6035(7) 0.097(3) Uani 1 1 d . . . H12 H 0.6071 0.4813 0.5730 0.117 Uiso 1 1 calc R A . C13 C 0.4961(9) 0.3858(8) 0.5780(5) 0.088(3) Uani 1 1 d . A . H13 H 0.4839 0.3627 0.5290 0.105 Uiso 1 1 calc R . . C14 C 0.4424(7) 0.3470(7) 0.6251(4) 0.070(2) Uani 1 1 d . . . H14 H 0.3944 0.2961 0.6085 0.084 Uiso 1 1 calc R A . C15 C 0.236(3) 0.2298(10) 0.9126(19) 0.035(6) Uani 0.50 1 d PDU A 1 H15 H 0.3103 0.2399 0.9366 0.042 Uiso 0.50 1 calc PR A 1 C16 C 0.249(3) 0.183(3) 0.844(3) 0.107(17) Uani 0.50 1 d PDU A 1 H16A H 0.2696 0.2338 0.8131 0.128 Uiso 0.50 1 calc PR A 1 H16B H 0.1819 0.1567 0.8152 0.128 Uiso 0.50 1 calc PR A 1 C17 C 0.331(2) 0.0990(15) 0.8586(11) 0.079(6) Uani 0.50 1 d PDU A 1 H17A H 0.3347 0.0693 0.8117 0.095 Uiso 0.50 1 calc PR A 1 H17B H 0.3993 0.1251 0.8841 0.095 Uiso 0.50 1 calc PR A 1 C18 C 0.297(2) 0.022(2) 0.9072(17) 0.084(9) Uani 0.50 1 d PDU A 1 H18A H 0.2303 -0.0063 0.8811 0.101 Uiso 0.50 1 calc PR A 1 H18B H 0.3486 -0.0308 0.9200 0.101 Uiso 0.50 1 calc PR A 1 C19 C 0.2892(17) 0.0741(14) 0.9753(14) 0.066(7) Uani 0.50 1 d PDU A 1 H19A H 0.3589 0.0942 1.0035 0.079 Uiso 0.50 1 calc PR A 1 H19B H 0.2632 0.0277 1.0062 0.079 Uiso 0.50 1 calc PR A 1 C20 C 0.2191(15) 0.1648(12) 0.9618(10) 0.071(5) Uani 0.50 1 d PDU A 1 H20A H 0.1470 0.1427 0.9450 0.085 Uiso 0.50 1 calc PR A 1 H20B H 0.2274 0.1987 1.0093 0.085 Uiso 0.50 1 calc PR A 1 C15A C 0.256(3) 0.2363(14) 0.913(3) 0.081(13) Uani 0.50 1 d PDU A 2 H15A H 0.1933 0.2032 0.9202 0.097 Uiso 0.50 1 calc PR A 2 C16A C 0.261(2) 0.1803(12) 0.8429(13) 0.034(6) Uani 0.50 1 d PDU A 2 H16C H 0.3243 0.1994 0.8300 0.040 Uiso 0.50 1 calc PR A 2 H16D H 0.2019 0.2007 0.8019 0.040 Uiso 0.50 1 calc PR A 2 C17A C 0.2588(16) 0.0657(11) 0.8498(10) 0.067(5) Uani 0.50 1 d PDU A 2 H17C H 0.1918 0.0437 0.8557 0.080 Uiso 0.50 1 calc PR A 2 H17D H 0.2703 0.0346 0.8054 0.080 Uiso 0.50 1 calc PR A 2 C18A C 0.3472(19) 0.0383(18) 0.9194(14) 0.077(8) Uani 0.50 1 d PDU A 2 H18C H 0.3471 -0.0330 0.9267 0.093 Uiso 0.50 1 calc PR A 2 H18D H 0.4139 0.0562 0.9107 0.093 Uiso 0.50 1 calc PR A 2 C19A C 0.337(2) 0.0882(16) 0.9883(16) 0.093(11) Uani 0.50 1 d PDU A 2 H19C H 0.3989 0.0742 1.0291 0.112 Uiso 0.50 1 calc PR A 2 H19D H 0.2767 0.0621 1.0020 0.112 Uiso 0.50 1 calc PR A 2 C20A C 0.3255(16) 0.2011(12) 0.9773(9) 0.068(5) Uani 0.50 1 d PDU A 2 H20C H 0.3053 0.2282 1.0200 0.082 Uiso 0.50 1 calc PR A 2 H20D H 0.3940 0.2280 0.9789 0.082 Uiso 0.50 1 calc PR A 2 C21 C 0.0739(6) 0.3608(6) 0.8309(4) 0.054(2) Uani 1 1 d . A . H21 H 0.0395 0.4213 0.8417 0.065 Uiso 1 1 calc R . . C22 C -0.0014(6) 0.2775(7) 0.8334(5) 0.076(3) Uani 1 1 d . . . H22A H 0.0256 0.2155 0.8194 0.091 Uiso 1 1 calc R A . H22B H -0.0084 0.2705 0.8841 0.091 Uiso 1 1 calc R . . C23 C -0.1071(7) 0.2992(8) 0.7802(6) 0.092(3) Uani 1 1 d . A . H23A H -0.1531 0.2433 0.7804 0.111 Uiso 1 1 calc R . . H23B H -0.1370 0.3568 0.7984 0.111 Uiso 1 1 calc R . . C24 C -0.1034(8) 0.3182(9) 0.7025(6) 0.097(3) Uani 1 1 d . . . H24A H -0.1722 0.3387 0.6729 0.117 Uiso 1 1 calc R A . H24B H -0.0853 0.2572 0.6810 0.117 Uiso 1 1 calc R . . C25 C -0.0263(8) 0.3959(8) 0.6986(6) 0.099(3) Uani 1 1 d . A . H25A H -0.0504 0.4593 0.7124 0.119 Uiso 1 1 calc R . . H25B H -0.0210 0.4011 0.6475 0.119 Uiso 1 1 calc R . . C26 C 0.0813(7) 0.3731(6) 0.7506(4) 0.066(2) Uani 1 1 d . . . H26A H 0.1292 0.4268 0.7483 0.079 Uiso 1 1 calc R A . H26B H 0.1084 0.3126 0.7343 0.079 Uiso 1 1 calc R . . C27 C 0.1792(6) 0.4010(6) 0.9878(4) 0.057(2) Uani 1 1 d . A . H27 H 0.1423 0.4645 0.9756 0.068 Uiso 1 1 calc R . . C28 C 0.2755(8) 0.4265(10) 1.0428(5) 0.114(4) Uani 1 1 d D . . H28A H 0.3158 0.4715 1.0204 0.137 Uiso 1 1 calc R A . H28B H 0.3168 0.3669 1.0581 0.137 Uiso 1 1 calc R . . C29 C 0.2539(11) 0.4762(13) 1.1124(7) 0.189(9) Uani 1 1 d D A . H29A H 0.3200 0.4866 1.1499 0.227 Uiso 1 1 calc R . . H29B H 0.2223 0.5408 1.0982 0.227 Uiso 1 1 calc R . . C30 C 0.1880(10) 0.4201(11) 1.1441(5) 0.119(5) Uani 1 1 d . . . H30A H 0.1733 0.4569 1.1853 0.143 Uiso 1 1 calc R A . H30B H 0.2230 0.3589 1.1642 0.143 Uiso 1 1 calc R . . C31 C 0.0907(10) 0.3971(11) 1.0892(6) 0.144(6) Uani 1 1 d D A . H31A H 0.0533 0.4583 1.0721 0.173 Uiso 1 1 calc R . . H31B H 0.0474 0.3569 1.1125 0.173 Uiso 1 1 calc R . . C32 C 0.1094(11) 0.3405(11) 1.0207(6) 0.148(6) Uani 1 1 d D . . H32A H 0.1414 0.2765 1.0365 0.177 Uiso 1 1 calc R A . H32B H 0.0432 0.3293 0.9836 0.177 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 0.0551(4) 0.0401(3) 0.0447(3) -0.0011(3) 0.0179(3) -0.0036(3) S1 0.0661(14) 0.0627(14) 0.0473(11) -0.0071(10) 0.0092(10) 0.0009(11) P1 0.0528(12) 0.0466(12) 0.0467(11) -0.0029(9) 0.0194(10) -0.0039(10) Br1 0.0926(7) 0.0554(6) 0.0916(7) 0.0051(5) 0.0333(6) 0.0153(5) Br2 0.0842(7) 0.0648(6) 0.0697(6) 0.0117(5) 0.0200(5) -0.0206(5) N1 0.054(4) 0.054(4) 0.041(3) -0.008(3) 0.019(3) -0.013(3) C1 0.058(5) 0.034(4) 0.047(4) -0.006(3) 0.022(4) -0.005(3) C2 0.045(5) 0.053(5) 0.061(5) 0.003(4) 0.015(4) -0.004(4) C3 0.068(6) 0.079(7) 0.076(6) -0.021(5) 0.024(5) 0.009(5) C4 0.074(7) 0.098(8) 0.108(8) -0.010(7) 0.042(7) 0.017(6) C5 0.098(8) 0.073(7) 0.114(9) 0.009(7) 0.011(7) 0.035(6) C6 0.075(7) 0.081(7) 0.073(6) -0.001(5) -0.003(5) 0.017(6) C7 0.058(5) 0.047(5) 0.066(5) -0.007(4) 0.020(4) -0.004(4) C8 0.055(5) 0.060(5) 0.044(4) -0.009(4) 0.015(4) 0.000(4) C9 0.056(5) 0.058(5) 0.045(4) 0.000(4) 0.017(4) 0.000(4) C10 0.097(8) 0.114(9) 0.062(5) -0.018(6) 0.041(5) -0.033(7) C11 0.111(9) 0.122(10) 0.099(8) -0.017(7) 0.051(7) -0.051(7) C12 0.112(9) 0.094(8) 0.104(9) 0.025(7) 0.059(7) -0.016(7) C13 0.126(9) 0.097(8) 0.049(5) 0.007(5) 0.039(6) -0.014(7) C14 0.084(7) 0.072(6) 0.056(5) -0.001(5) 0.021(5) -0.016(5) C15 0.053(14) 0.031(9) 0.027(11) -0.003(8) 0.018(9) 0.003(8) C16 0.10(2) 0.11(2) 0.12(2) 0.016(16) 0.023(16) 0.020(15) C17 0.099(13) 0.090(14) 0.067(11) -0.004(10) 0.055(11) 0.018(12) C18 0.102(17) 0.054(14) 0.093(15) -0.003(12) 0.018(13) -0.010(12) C19 0.076(14) 0.058(11) 0.063(14) 0.019(10) 0.016(11) 0.007(10) C20 0.084(12) 0.073(11) 0.065(10) 0.004(9) 0.034(9) -0.005(9) C15A 0.039(15) 0.14(3) 0.07(2) -0.009(19) 0.025(13) -0.020(15) C16A 0.047(12) 0.030(11) 0.026(9) -0.010(8) 0.014(8) -0.011(9) C17A 0.089(15) 0.044(11) 0.072(12) 0.009(9) 0.030(12) 0.010(11) C18A 0.10(2) 0.024(11) 0.11(2) -0.013(11) 0.031(17) -0.005(12) C19A 0.09(2) 0.11(2) 0.044(11) 0.001(12) -0.035(14) -0.014(15) C20A 0.102(15) 0.050(11) 0.046(9) -0.006(8) 0.007(10) 0.011(10) C21 0.049(5) 0.053(5) 0.060(5) -0.002(4) 0.014(4) -0.003(4) C22 0.055(6) 0.084(7) 0.088(6) -0.002(5) 0.019(5) -0.016(5) C23 0.052(6) 0.105(8) 0.117(9) -0.030(7) 0.018(6) -0.016(5) C24 0.066(7) 0.116(10) 0.097(8) -0.017(7) 0.000(6) 0.006(7) C25 0.091(8) 0.114(9) 0.081(7) -0.001(6) 0.003(6) 0.007(7) C26 0.072(6) 0.059(6) 0.059(5) -0.001(4) 0.002(5) -0.005(5) C27 0.063(5) 0.066(5) 0.049(4) -0.004(4) 0.027(4) -0.006(4) C28 0.091(8) 0.200(13) 0.061(6) -0.060(7) 0.037(6) -0.053(8) C29 0.158(14) 0.32(2) 0.113(10) -0.136(13) 0.084(10) -0.130(15) C30 0.139(11) 0.179(13) 0.050(6) -0.012(7) 0.045(7) 0.027(9) C31 0.110(10) 0.256(18) 0.088(8) -0.033(10) 0.066(8) -0.035(11) C32 0.160(12) 0.220(15) 0.085(8) -0.046(9) 0.071(8) -0.096(12) _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 C1 1.958(7) . ? Pd1 P1 2.302(2) . ? Pd1 Br1 2.4658(11) . ? Pd1 Br2 2.4796(10) . ? S1 C1 1.709(7) . ? S1 C7 1.744(8) . ? P1 C15A 1.820(11) . ? P1 C15 1.827(10) . ? P1 C21 1.837(7) . ? P1 C27 1.857(7) . ? N1 C1 1.335(8) . ? N1 C2 1.411(9) . ? N1 C8 1.481(8) . ? C2 C3 1.385(11) . ? C2 C7 1.405(10) . ? C3 C4 1.358(12) . ? C4 C5 1.389(13) . ? C5 C6 1.363(13) . ? C6 C7 1.367(11) . ? C8 C9 1.513(10) . ? C9 C10 1.343(11) . ? C9 C14 1.372(10) . ? C10 C11 1.391(13) . ? C11 C12 1.345(14) . ? C12 C13 1.358(13) . ? C13 C14 1.383(12) . ? C15 C20 1.34(3) . ? C15 C16 1.49(6) . ? C16 C17 1.560(19) . ? C17 C18 1.528(17) . ? C18 C19 1.48(4) . ? C19 C20 1.530(16) . ? C15A C20A 1.39(4) . ? C15A C16A 1.53(6) . ? C16A C17A 1.565(16) . ? C17A C18A 1.551(17) . ? C18A C19A 1.49(4) . ? C19A C20A 1.551(17) . ? C21 C22 1.526(11) . ? C21 C26 1.540(10) . ? C22 C23 1.526(12) . ? C23 C24 1.488(13) . ? C24 C25 1.492(14) . ? C25 C26 1.538(12) . ? C27 C28 1.460(11) . ? C27 C32 1.494(12) . ? C28 C29 1.560(11) . ? C29 C30 1.411(17) . ? C30 C31 1.461(15) . ? C31 C32 1.570(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 P1 94.4(2) . . ? C1 Pd1 Br1 175.8(2) . . ? P1 Pd1 Br1 89.31(6) . . ? C1 Pd1 Br2 86.2(2) . . ? P1 Pd1 Br2 175.65(6) . . ? Br1 Pd1 Br2 89.96(4) . . ? C1 S1 C7 92.8(4) . . ? C15A P1 C15 9(2) . . ? C15A P1 C21 111.6(15) . . ? C15 P1 C21 104.9(12) . . ? C15A P1 C27 107.5(17) . . ? C15 P1 C27 105.0(11) . . ? C21 P1 C27 105.8(4) . . ? C15A P1 Pd1 116.3(14) . . ? C15 P1 Pd1 124.9(12) . . ? C21 P1 Pd1 109.2(3) . . ? C27 P1 Pd1 105.7(3) . . ? C1 N1 C2 116.0(6) . . ? C1 N1 C8 122.1(6) . . ? C2 N1 C8 121.9(6) . . ? N1 C1 S1 110.7(5) . . ? N1 C1 Pd1 130.7(5) . . ? S1 C1 Pd1 118.5(4) . . ? C3 C2 C7 121.2(8) . . ? C3 C2 N1 127.7(7) . . ? C7 C2 N1 110.8(7) . . ? C4 C3 C2 116.9(9) . . ? C3 C4 C5 121.9(9) . . ? C6 C5 C4 121.4(9) . . ? C5 C6 C7 118.1(9) . . ? C6 C7 C2 120.4(8) . . ? C6 C7 S1 130.0(7) . . ? C2 C7 S1 109.6(6) . . ? N1 C8 C9 113.5(6) . . ? C10 C9 C14 119.3(8) . . ? C10 C9 C8 121.3(7) . . ? C14 C9 C8 119.2(7) . . ? C9 C10 C11 120.8(9) . . ? C12 C11 C10 119.1(10) . . ? C11 C12 C13 121.3(10) . . ? C12 C13 C14 118.9(9) . . ? C9 C14 C13 120.3(9) . . ? C20 C15 C16 113(2) . . ? C20 C15 P1 131(2) . . ? C16 C15 P1 112(2) . . ? C15 C16 C17 113(3) . . ? C18 C17 C16 108(3) . . ? C19 C18 C17 106(2) . . ? C18 C19 C20 115(2) . . ? C15 C20 C19 116.1(19) . . ? C20A C15A C16A 113.2(17) . . ? C20A C15A P1 126(3) . . ? C16A C15A P1 116(3) . . ? C15A C16A C17A 115(2) . . ? C18A C17A C16A 106.4(18) . . ? C19A C18A C17A 113(2) . . ? C18A C19A C20A 111(2) . . ? C15A C20A C19A 118.4(17) . . ? C22 C21 C26 109.0(7) . . ? C22 C21 P1 118.3(6) . . ? C26 C21 P1 112.5(5) . . ? C23 C22 C21 110.0(7) . . ? C24 C23 C22 113.7(8) . . ? C23 C24 C25 112.0(9) . . ? C24 C25 C26 111.7(8) . . ? C25 C26 C21 110.1(8) . . ? C28 C27 C32 112.0(8) . . ? C28 C27 P1 112.2(6) . . ? C32 C27 P1 118.1(6) . . ? C27 C28 C29 111.3(9) . . ? C30 C29 C28 113.1(11) . . ? C29 C30 C31 111.1(10) . . ? C30 C31 C32 111.8(10) . . ? C27 C32 C31 108.5(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.065 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.116 # Attachment 'complex_6.cif' data_5445a _database_code_depnum_ccdc_archive 'CCDC 658818' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 Br2 N P Pd S' _chemical_formula_weight 723.89 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.244(3) _cell_length_b 14.302(3) _cell_length_c 16.013(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.398(3) _cell_angle_gamma 90.00 _cell_volume 3077.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2206 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 20.69 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 3.337 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.4148 _exptl_absorpt_correction_T_max 0.7761 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _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 21001 _diffrn_reflns_av_R_equivalents 0.0808 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7058 _reflns_number_gt 4070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0799P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7058 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.72749(4) 0.06330(3) 0.07794(3) 0.04398(17) Uani 1 1 d . . . Br1 Br 0.86438(8) -0.03664(6) 0.06791(6) 0.0822(3) Uani 1 1 d . . . Br2 Br 0.69748(6) -0.04609(5) 0.18691(5) 0.0633(2) Uani 1 1 d . . . P1 P 0.74638(13) 0.16301(11) -0.02720(10) 0.0437(4) Uani 1 1 d . . . S1 S 0.49602(12) 0.12006(11) 0.03466(10) 0.0463(4) Uani 1 1 d . . . N1 N 0.6272(3) 0.1980(3) 0.1619(3) 0.0361(11) Uani 1 1 d . . . C1 C 0.6186(5) 0.1362(4) 0.0964(3) 0.0397(14) Uani 1 1 d . . . C2 C 0.5367(4) 0.2350(4) 0.1640(4) 0.0381(13) Uani 1 1 d . . . C3 C 0.5260(5) 0.3049(4) 0.2224(4) 0.0443(15) Uani 1 1 d . . . H3 H 0.5815 0.3328 0.2644 0.053 Uiso 1 1 calc R . . C4 C 0.4309(5) 0.3300(5) 0.2149(4) 0.0503(16) Uani 1 1 d . . . H4 H 0.4208 0.3764 0.2526 0.060 Uiso 1 1 calc R . . C5 C 0.3485(5) 0.2886(5) 0.1528(5) 0.0599(19) Uani 1 1 d . . . H5 H 0.2843 0.3063 0.1512 0.072 Uiso 1 1 calc R . . C6 C 0.3584(5) 0.2223(5) 0.0932(4) 0.0536(17) Uani 1 1 d . . . H6 H 0.3027 0.1954 0.0505 0.064 Uiso 1 1 calc R . . C7 C 0.4557(5) 0.1973(4) 0.1002(4) 0.0428(14) Uani 1 1 d . . . C8 C 0.7214(5) 0.2176(4) 0.2321(4) 0.0458(15) Uani 1 1 d . . . H8A H 0.7304 0.2854 0.2390 0.055 Uiso 1 1 calc R . . H8B H 0.7764 0.1925 0.2149 0.055 Uiso 1 1 calc R . . C9 C 0.7255(5) 0.1748(5) 0.3209(4) 0.0592(18) Uani 1 1 d . . . H9A H 0.6787 0.2079 0.3436 0.071 Uiso 1 1 calc R . . H9B H 0.7050 0.1092 0.3120 0.071 Uiso 1 1 calc R . . C10 C 0.8252(7) 0.1805(7) 0.3860(6) 0.101(3) Uani 1 1 d . . . H10A H 0.8659 0.1303 0.3758 0.152 Uiso 1 1 calc R . . H10B H 0.8212 0.1748 0.4451 0.152 Uiso 1 1 calc R . . H10C H 0.8548 0.2402 0.3804 0.152 Uiso 1 1 calc R . . C11 C 0.6762(5) 0.2744(4) -0.0379(4) 0.0445(15) Uani 1 1 d . . . H11 H 0.6111 0.2569 -0.0326 0.053 Uiso 1 1 calc R . . C12 C 0.7228(5) 0.3418(4) 0.0380(4) 0.0518(16) Uani 1 1 d . . . H12A H 0.7849 0.3664 0.0329 0.062 Uiso 1 1 calc R . . H12B H 0.7392 0.3080 0.0942 0.062 Uiso 1 1 calc R . . C13 C 0.6533(6) 0.4235(5) 0.0383(5) 0.070(2) Uani 1 1 d . . . H13A H 0.5925 0.3997 0.0467 0.084 Uiso 1 1 calc R . . H13B H 0.6861 0.4659 0.0874 0.084 Uiso 1 1 calc R . . C14 C 0.6269(6) 0.4760(5) -0.0490(5) 0.073(2) Uani 1 1 d . . . H14A H 0.5790 0.5256 -0.0502 0.088 Uiso 1 1 calc R . . H14B H 0.6869 0.5054 -0.0542 0.088 Uiso 1 1 calc R . . C15 C 0.5829(6) 0.4108(5) -0.1263(5) 0.070(2) Uani 1 1 d . . . H15A H 0.5703 0.4457 -0.1816 0.085 Uiso 1 1 calc R . . H15B H 0.5189 0.3873 -0.1246 0.085 Uiso 1 1 calc R . . C16 C 0.6513(5) 0.3278(5) -0.1254(4) 0.0548(17) Uani 1 1 d . . . H16A H 0.6183 0.2858 -0.1748 0.066 Uiso 1 1 calc R . . H16B H 0.7128 0.3505 -0.1331 0.066 Uiso 1 1 calc R . . C17 C 0.6957(5) 0.1112(4) -0.1392(4) 0.0477(16) Uani 1 1 d . . . H17 H 0.6991 0.1608 -0.1812 0.057 Uiso 1 1 calc R . . C18 C 0.5868(6) 0.0870(6) -0.1617(4) 0.0633(19) Uani 1 1 d . . . H18A H 0.5502 0.1422 -0.1531 0.076 Uiso 1 1 calc R . . H18B H 0.5793 0.0377 -0.1219 0.076 Uiso 1 1 calc R . . C19 C 0.5439(7) 0.0542(6) -0.2568(5) 0.076(2) Uani 1 1 d . . . H19A H 0.4748 0.0345 -0.2685 0.091 Uiso 1 1 calc R . . H19B H 0.5435 0.1066 -0.2963 0.091 Uiso 1 1 calc R . . C20 C 0.6017(8) -0.0258(6) -0.2771(5) 0.091(3) Uani 1 1 d . . . H20A H 0.5932 -0.0814 -0.2447 0.109 Uiso 1 1 calc R . . H20B H 0.5748 -0.0400 -0.3405 0.109 Uiso 1 1 calc R . . C21 C 0.7108(7) -0.0040(6) -0.2525(5) 0.082(3) Uani 1 1 d . . . H21A H 0.7204 0.0448 -0.2919 0.099 Uiso 1 1 calc R . . H21B H 0.7465 -0.0600 -0.2606 0.099 Uiso 1 1 calc R . . C22 C 0.7539(6) 0.0290(5) -0.1564(5) 0.066(2) Uani 1 1 d . . . H22A H 0.7521 -0.0226 -0.1167 0.080 Uiso 1 1 calc R . . H22B H 0.8236 0.0473 -0.1436 0.080 Uiso 1 1 calc R . . C23 C 0.8779(5) 0.1894(4) -0.0109(4) 0.0460(15) Uani 1 1 d . . . H23 H 0.9058 0.1303 -0.0246 0.055 Uiso 1 1 calc R . . C24 C 0.8961(4) 0.2607(4) -0.0739(4) 0.0445(14) Uani 1 1 d . . . H24A H 0.8731 0.3222 -0.0621 0.053 Uiso 1 1 calc R . . H24B H 0.8579 0.2433 -0.1350 0.053 Uiso 1 1 calc R . . C25 C 1.0068(5) 0.2658(5) -0.0633(4) 0.0565(18) Uani 1 1 d . . . H25A H 1.0282 0.2057 -0.0803 0.068 Uiso 1 1 calc R . . H25B H 1.0170 0.3139 -0.1030 0.068 Uiso 1 1 calc R . . C26 C 1.0686(5) 0.2883(6) 0.0299(5) 0.072(2) Uani 1 1 d . . . H26A H 1.0516 0.3510 0.0452 0.087 Uiso 1 1 calc R . . H26B H 1.1392 0.2882 0.0354 0.087 Uiso 1 1 calc R . . C27 C 1.0508(5) 0.2176(6) 0.0933(5) 0.074(2) Uani 1 1 d . . . H27A H 1.0899 0.2350 0.1541 0.088 Uiso 1 1 calc R . . H27B H 1.0735 0.1560 0.0813 0.088 Uiso 1 1 calc R . . C28 C 0.9407(5) 0.2119(5) 0.0848(4) 0.0567(18) Uani 1 1 d . . . H28A H 0.9192 0.2717 0.1024 0.068 Uiso 1 1 calc R . . H28B H 0.9313 0.1632 0.1243 0.068 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 0.0809(4) 0.0201(2) 0.0363(3) 0.00323(18) 0.0265(2) 0.0093(2) Br1 0.1417(8) 0.0484(5) 0.0794(5) 0.0236(4) 0.0675(6) 0.0495(5) Br2 0.0987(6) 0.0357(4) 0.0598(4) 0.0207(3) 0.0321(4) 0.0080(4) P1 0.0757(11) 0.0254(8) 0.0360(8) 0.0029(6) 0.0266(8) 0.0066(8) S1 0.0671(11) 0.0289(8) 0.0389(8) -0.0022(6) 0.0122(7) -0.0059(7) N1 0.050(3) 0.029(3) 0.031(2) -0.003(2) 0.015(2) -0.003(2) C1 0.072(4) 0.014(3) 0.038(3) 0.007(2) 0.024(3) -0.003(3) C2 0.056(4) 0.028(3) 0.035(3) 0.003(2) 0.021(3) 0.001(3) C3 0.061(4) 0.035(3) 0.038(3) 0.004(3) 0.017(3) 0.003(3) C4 0.070(5) 0.039(4) 0.049(4) 0.009(3) 0.030(3) 0.018(3) C5 0.051(4) 0.063(5) 0.064(4) 0.012(4) 0.017(4) 0.012(4) C6 0.050(4) 0.049(4) 0.058(4) 0.004(3) 0.012(3) 0.000(3) C7 0.063(4) 0.028(3) 0.039(3) 0.004(3) 0.018(3) -0.002(3) C8 0.061(4) 0.032(3) 0.048(4) -0.003(3) 0.022(3) 0.004(3) C9 0.083(5) 0.048(4) 0.039(3) 0.001(3) 0.011(4) -0.002(4) C10 0.105(7) 0.097(8) 0.077(6) -0.004(5) -0.002(5) -0.004(6) C11 0.067(4) 0.028(3) 0.045(3) 0.005(3) 0.027(3) 0.005(3) C12 0.085(5) 0.029(3) 0.051(4) 0.001(3) 0.036(3) 0.006(3) C13 0.097(6) 0.040(4) 0.084(5) -0.001(4) 0.044(5) 0.015(4) C14 0.105(6) 0.032(4) 0.090(6) 0.017(4) 0.042(5) 0.029(4) C15 0.071(5) 0.057(5) 0.085(5) 0.031(4) 0.029(4) 0.017(4) C16 0.078(5) 0.036(4) 0.053(4) 0.014(3) 0.026(3) 0.003(3) C17 0.082(5) 0.031(3) 0.035(3) 0.000(3) 0.026(3) -0.008(3) C18 0.086(5) 0.058(5) 0.050(4) -0.006(3) 0.027(4) -0.009(4) C19 0.103(6) 0.072(6) 0.053(4) -0.012(4) 0.028(4) -0.027(5) C20 0.176(10) 0.057(5) 0.057(5) -0.023(4) 0.060(6) -0.037(6) C21 0.137(8) 0.059(5) 0.069(5) -0.023(4) 0.058(5) -0.011(5) C22 0.103(6) 0.043(4) 0.062(4) -0.012(3) 0.040(4) 0.005(4) C23 0.069(4) 0.033(3) 0.041(3) 0.002(3) 0.025(3) 0.014(3) C24 0.057(4) 0.034(3) 0.045(3) 0.000(3) 0.020(3) 0.010(3) C25 0.066(5) 0.050(4) 0.059(4) 0.002(3) 0.028(4) 0.019(3) C26 0.057(4) 0.096(7) 0.063(5) -0.005(5) 0.019(4) 0.012(4) C27 0.073(5) 0.096(7) 0.046(4) -0.007(4) 0.012(4) 0.035(5) C28 0.080(5) 0.051(4) 0.042(4) 0.001(3) 0.024(3) 0.017(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 Pd1 C1 1.971(6) . ? Pd1 P1 2.2895(15) . ? Pd1 Br1 2.4656(9) . ? Pd1 Br2 2.4841(8) . ? P1 C23 1.843(7) . ? P1 C17 1.852(6) . ? P1 C11 1.858(6) . ? S1 C1 1.713(6) . ? S1 C7 1.747(6) . ? N1 C1 1.345(7) . ? N1 C2 1.405(7) . ? N1 C8 1.464(7) . ? C2 C7 1.372(8) . ? C2 C3 1.410(8) . ? C3 C4 1.368(8) . ? C4 C5 1.394(9) . ? C5 C6 1.385(10) . ? C6 C7 1.400(9) . ? C8 C9 1.531(8) . ? C9 C10 1.457(10) . ? C11 C12 1.520(8) . ? C11 C16 1.531(8) . ? C12 C13 1.533(9) . ? C13 C14 1.521(10) . ? C14 C15 1.509(11) . ? C15 C16 1.533(9) . ? C17 C18 1.511(9) . ? C17 C22 1.515(9) . ? C18 C19 1.515(9) . ? C19 C20 1.507(12) . ? C20 C21 1.503(12) . ? C21 C22 1.531(10) . ? C23 C24 1.515(8) . ? C23 C28 1.531(8) . ? C24 C25 1.531(8) . ? C25 C26 1.495(9) . ? C26 C27 1.513(11) . ? C27 C28 1.530(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 P1 94.10(15) . . ? C1 Pd1 Br1 174.39(15) . . ? P1 Pd1 Br1 91.40(5) . . ? C1 Pd1 Br2 84.27(15) . . ? P1 Pd1 Br2 176.90(5) . . ? Br1 Pd1 Br2 90.28(3) . . ? C23 P1 C17 105.7(3) . . ? C23 P1 C11 109.2(3) . . ? C17 P1 C11 103.3(3) . . ? C23 P1 Pd1 112.70(19) . . ? C17 P1 Pd1 111.1(2) . . ? C11 P1 Pd1 114.22(19) . . ? C1 S1 C7 92.5(3) . . ? C1 N1 C2 114.9(5) . . ? C1 N1 C8 123.2(5) . . ? C2 N1 C8 121.6(4) . . ? N1 C1 S1 110.4(4) . . ? N1 C1 Pd1 126.3(4) . . ? S1 C1 Pd1 123.0(3) . . ? C7 C2 N1 112.6(5) . . ? C7 C2 C3 121.6(5) . . ? N1 C2 C3 125.8(5) . . ? C4 C3 C2 116.7(6) . . ? C3 C4 C5 121.8(6) . . ? C6 C5 C4 121.8(6) . . ? C5 C6 C7 116.4(6) . . ? C2 C7 C6 121.6(6) . . ? C2 C7 S1 109.5(4) . . ? C6 C7 S1 128.9(5) . . ? N1 C8 C9 112.3(5) . . ? C10 C9 C8 111.7(7) . . ? C12 C11 C16 108.8(5) . . ? C12 C11 P1 113.0(4) . . ? C16 C11 P1 117.8(4) . . ? C11 C12 C13 112.0(6) . . ? C14 C13 C12 109.6(6) . . ? C15 C14 C13 110.9(6) . . ? C14 C15 C16 112.4(6) . . ? C11 C16 C15 110.4(5) . . ? C18 C17 C22 111.1(6) . . ? C18 C17 P1 111.2(4) . . ? C22 C17 P1 115.2(5) . . ? C17 C18 C19 110.4(6) . . ? C20 C19 C18 112.7(7) . . ? C21 C20 C19 112.2(7) . . ? C20 C21 C22 111.2(7) . . ? C17 C22 C21 111.1(7) . . ? C24 C23 C28 110.7(5) . . ? C24 C23 P1 115.7(4) . . ? C28 C23 P1 114.4(4) . . ? C23 C24 C25 110.9(5) . . ? C26 C25 C24 111.3(5) . . ? C25 C26 C27 110.6(7) . . ? C26 C27 C28 111.8(6) . . ? C27 C28 C23 109.9(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.710 _refine_diff_density_min -1.199 _refine_diff_density_rms 0.158 # Attachment 'complex_7.cif' data_5426 _database_code_depnum_ccdc_archive 'CCDC 658819' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H25 Br2 N2 P Pd S' _chemical_formula_weight 754.78 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 12.2745(7) _cell_length_b 19.0370(12) _cell_length_c 13.4604(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.8850(10) _cell_angle_gamma 90.00 _cell_volume 2957.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4793 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.25 _exptl_crystal_description PLATE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 3.477 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.4427 _exptl_absorpt_correction_T_max 0.7224 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _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 20682 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6794 _reflns_number_gt 5301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0457P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6794 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.633523(19) 0.136365(11) 1.017432(17) 0.02142(7) Uani 1 1 d . . . Br1 Br 0.83618(3) 0.157889(18) 1.13120(3) 0.03524(10) Uani 1 1 d . . . Br2 Br 0.56014(3) 0.141537(17) 1.16665(3) 0.03426(9) Uani 1 1 d . . . P1 P 0.69824(7) 0.12332(4) 0.87999(6) 0.02364(17) Uani 1 1 d . . . S1 S 0.41748(7) 0.03911(4) 0.88985(6) 0.02752(18) Uani 1 1 d . . . N1 N 0.3945(2) 0.17026(12) 0.87853(18) 0.0229(5) Uani 1 1 d . . . N2 N 0.7126(3) 0.26043(16) 0.8380(3) 0.0508(8) Uani 1 1 d . . . C1 C 0.4720(2) 0.12127(14) 0.9247(2) 0.0224(6) Uani 1 1 d . . . C2 C 0.2872(3) 0.14467(15) 0.8111(2) 0.0264(7) Uani 1 1 d . . . C3 C 0.1928(3) 0.18446(19) 0.7509(3) 0.0381(8) Uani 1 1 d . . . H3 H 0.1951 0.2338 0.7517 0.046 Uiso 1 1 calc R . . C4 C 0.0955(3) 0.1482(2) 0.6901(3) 0.0494(10) Uani 1 1 d . . . H4 H 0.0296 0.1733 0.6491 0.059 Uiso 1 1 calc R . . C5 C 0.0936(3) 0.0748(2) 0.6885(3) 0.0521(11) Uani 1 1 d . . . H5 H 0.0259 0.0517 0.6464 0.063 Uiso 1 1 calc R . . C6 C 0.1873(3) 0.03547(19) 0.7464(3) 0.0395(8) Uani 1 1 d . . . H6 H 0.1854 -0.0139 0.7442 0.047 Uiso 1 1 calc R . . C7 C 0.2852(3) 0.07175(16) 0.8085(2) 0.0283(7) Uani 1 1 d . . . C8 C 0.4202(3) 0.24576(15) 0.8920(2) 0.0289(7) Uani 1 1 d . . . H8A H 0.4070 0.2667 0.8224 0.035 Uiso 1 1 calc R . . H8B H 0.5024 0.2518 0.9337 0.035 Uiso 1 1 calc R . . C9 C 0.3492(3) 0.28484(16) 0.9453(2) 0.0298(7) Uani 1 1 d . . . C10 C 0.3311(3) 0.35589(17) 0.9250(3) 0.0422(9) Uani 1 1 d . . . H10 H 0.3599 0.3776 0.8762 0.051 Uiso 1 1 calc R . . C11 C 0.2709(4) 0.3954(2) 0.9756(3) 0.0563(12) Uani 1 1 d . . . H11 H 0.2610 0.4439 0.9627 0.068 Uiso 1 1 calc R . . C12 C 0.2262(4) 0.3641(2) 1.0441(3) 0.0534(11) Uani 1 1 d . . . H12 H 0.1837 0.3908 1.0770 0.064 Uiso 1 1 calc R . . C13 C 0.2429(3) 0.2935(2) 1.0654(3) 0.0504(10) Uani 1 1 d . . . H13 H 0.2122 0.2721 1.1129 0.060 Uiso 1 1 calc R . . C14 C 0.3052(3) 0.25403(18) 1.0166(3) 0.0381(8) Uani 1 1 d . . . H14 H 0.3176 0.2059 1.0321 0.046 Uiso 1 1 calc R . . C1A C 0.7769(3) 0.20027(16) 0.8600(2) 0.0259(7) Uani 1 1 d . . . C2A C 0.8910(3) 0.19925(19) 0.8675(3) 0.0414(9) Uani 1 1 d . . . H2A H 0.9336 0.1572 0.8839 0.050 Uiso 1 1 calc R . . C3A C 0.9434(4) 0.2604(2) 0.8507(3) 0.0515(10) Uani 1 1 d . . . H3A H 1.0218 0.2605 0.8558 0.062 Uiso 1 1 calc R . . C4A C 0.8786(4) 0.3210(2) 0.8264(3) 0.0541(11) Uani 1 1 d . . . H4A H 0.9122 0.3629 0.8141 0.065 Uiso 1 1 calc R . . C5A C 0.7677(4) 0.32006(19) 0.8204(3) 0.0517(11) Uani 1 1 d . . . H5A H 0.7251 0.3620 0.8034 0.062 Uiso 1 1 calc R . . C1B C 0.7914(3) 0.04694(15) 0.8949(2) 0.0268(7) Uani 1 1 d . . . C2B C 0.8464(3) 0.03203(16) 0.8235(3) 0.0335(7) Uani 1 1 d . . . H2B H 0.8414 0.0635 0.7683 0.040 Uiso 1 1 calc R . . C3B C 0.9083(3) -0.02889(19) 0.8336(3) 0.0402(8) Uani 1 1 d . . . H3B H 0.9481 -0.0380 0.7864 0.048 Uiso 1 1 calc R . . C4B C 0.9133(3) -0.07709(18) 0.9112(3) 0.0396(9) Uani 1 1 d . . . H4B H 0.9549 -0.1192 0.9160 0.047 Uiso 1 1 calc R . . C5B C 0.8572(3) -0.06330(17) 0.9819(3) 0.0386(8) Uani 1 1 d . . . H5B H 0.8597 -0.0961 1.0349 0.046 Uiso 1 1 calc R . . C6B C 0.7968(3) -0.00072(16) 0.9746(3) 0.0316(7) Uani 1 1 d . . . H6B H 0.7595 0.0094 1.0235 0.038 Uiso 1 1 calc R . . C1C C 0.5859(3) 0.10685(16) 0.7519(2) 0.0276(7) Uani 1 1 d . . . C2C C 0.5624(3) 0.03857(17) 0.7132(3) 0.0351(8) Uani 1 1 d . . . H2C H 0.6083 0.0010 0.7499 0.042 Uiso 1 1 calc R . . C3C C 0.4713(3) 0.02653(19) 0.6208(3) 0.0447(9) Uani 1 1 d . . . H3C H 0.4550 -0.0194 0.5942 0.054 Uiso 1 1 calc R . . C4C C 0.4048(3) 0.0813(2) 0.5680(3) 0.0474(10) Uani 1 1 d . . . H4C H 0.3431 0.0732 0.5047 0.057 Uiso 1 1 calc R . . C5C C 0.4282(3) 0.1482(2) 0.6073(3) 0.0469(10) Uani 1 1 d . . . H5C H 0.3820 0.1857 0.5707 0.056 Uiso 1 1 calc R . . C6C C 0.5172(3) 0.16110(17) 0.6986(3) 0.0314(7) Uani 1 1 d . . . H6C H 0.5315 0.2071 0.7251 0.038 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 0.02119(12) 0.02112(12) 0.02253(12) -0.00024(8) 0.00817(9) 0.00134(8) Br1 0.02702(18) 0.0433(2) 0.03294(18) -0.00754(14) 0.00696(14) -0.00140(14) Br2 0.0401(2) 0.03664(19) 0.03216(18) -0.00641(13) 0.02021(15) -0.00286(14) P1 0.0234(4) 0.0249(4) 0.0240(4) 0.0008(3) 0.0098(3) 0.0006(3) S1 0.0275(4) 0.0213(4) 0.0326(4) 0.0015(3) 0.0086(3) 0.0001(3) N1 0.0247(13) 0.0204(12) 0.0249(13) 0.0020(10) 0.0099(10) 0.0025(10) N2 0.053(2) 0.0419(18) 0.055(2) 0.0004(15) 0.0151(17) 0.0028(15) C1 0.0237(15) 0.0200(14) 0.0263(15) 0.0009(11) 0.0123(12) 0.0016(11) C2 0.0253(16) 0.0323(17) 0.0214(15) 0.0053(12) 0.0078(13) 0.0028(12) C3 0.0334(19) 0.042(2) 0.0359(19) 0.0074(15) 0.0081(15) 0.0086(15) C4 0.033(2) 0.059(3) 0.043(2) 0.0102(18) -0.0037(17) 0.0083(17) C5 0.0290(19) 0.074(3) 0.043(2) 0.000(2) -0.0016(17) -0.0128(19) C6 0.0360(19) 0.042(2) 0.038(2) -0.0024(15) 0.0084(16) -0.0098(15) C7 0.0259(16) 0.0332(17) 0.0259(16) 0.0029(13) 0.0088(13) -0.0004(13) C8 0.0322(18) 0.0202(15) 0.0361(18) 0.0030(12) 0.0140(14) 0.0041(12) C9 0.0314(17) 0.0288(16) 0.0252(16) -0.0005(12) 0.0045(14) 0.0067(13) C10 0.052(2) 0.035(2) 0.038(2) 0.0027(15) 0.0143(18) 0.0117(16) C11 0.077(3) 0.038(2) 0.053(3) -0.0036(18) 0.020(2) 0.025(2) C12 0.057(3) 0.064(3) 0.040(2) -0.0122(19) 0.018(2) 0.026(2) C13 0.048(2) 0.070(3) 0.038(2) 0.0016(19) 0.0207(19) 0.015(2) C14 0.040(2) 0.0369(19) 0.040(2) 0.0052(15) 0.0174(17) 0.0094(15) C1A 0.0293(17) 0.0272(15) 0.0217(15) 0.0025(12) 0.0092(13) -0.0021(12) C2A 0.038(2) 0.0376(19) 0.053(2) 0.0028(16) 0.0216(18) -0.0010(16) C3A 0.049(2) 0.051(2) 0.063(3) -0.008(2) 0.029(2) -0.0213(19) C4A 0.083(3) 0.041(2) 0.047(2) -0.0056(18) 0.033(2) -0.027(2) C5A 0.073(3) 0.0276(19) 0.049(2) 0.0028(16) 0.014(2) 0.0026(19) C1B 0.0232(15) 0.0255(15) 0.0323(17) -0.0035(12) 0.0101(13) 0.0001(12) C2B 0.0342(18) 0.0338(18) 0.0361(18) 0.0003(14) 0.0168(15) -0.0014(14) C3B 0.0342(19) 0.047(2) 0.048(2) -0.0123(17) 0.0256(17) -0.0013(16) C4B 0.0309(19) 0.0304(18) 0.057(2) -0.0061(16) 0.0137(17) 0.0050(14) C5B 0.038(2) 0.0295(18) 0.050(2) 0.0052(15) 0.0164(17) 0.0043(14) C6B 0.0294(17) 0.0326(17) 0.0344(18) 0.0023(14) 0.0128(14) 0.0033(13) C1C 0.0276(16) 0.0337(17) 0.0234(15) -0.0001(12) 0.0111(13) -0.0003(13) C2C 0.0376(19) 0.0324(18) 0.0332(18) 0.0003(14) 0.0094(15) -0.0028(14) C3C 0.050(2) 0.039(2) 0.039(2) -0.0084(16) 0.0074(18) -0.0102(17) C4C 0.041(2) 0.059(2) 0.036(2) -0.0037(18) 0.0057(17) -0.0078(18) C5C 0.043(2) 0.046(2) 0.047(2) 0.0083(17) 0.0100(18) 0.0085(17) C6C 0.0335(18) 0.0287(16) 0.0329(18) -0.0017(13) 0.0127(15) 0.0003(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 C1 1.972(3) . ? Pd1 P1 2.2616(8) . ? Pd1 Br2 2.4669(4) . ? Pd1 Br1 2.4717(4) . ? P1 C1B 1.818(3) . ? P1 C1A 1.824(3) . ? P1 C1C 1.832(3) . ? S1 C1 1.703(3) . ? S1 C7 1.736(3) . ? N1 C1 1.326(4) . ? N1 C2 1.408(4) . ? N1 C8 1.469(4) . ? N2 C1A 1.365(4) . ? N2 C5A 1.383(5) . ? C2 C7 1.389(4) . ? C2 C3 1.390(4) . ? C3 C4 1.381(5) . ? C4 C5 1.398(5) . ? C5 C6 1.372(5) . ? C6 C7 1.392(4) . ? C8 C9 1.501(4) . ? C9 C14 1.382(5) . ? C9 C10 1.383(4) . ? C10 C11 1.386(5) . ? C11 C12 1.361(6) . ? C12 C13 1.375(5) . ? C13 C14 1.387(5) . ? C1A C2A 1.370(5) . ? C2A C3A 1.385(5) . ? C3A C4A 1.376(6) . ? C4A C5A 1.335(6) . ? C1B C2B 1.379(5) . ? C1B C6B 1.390(4) . ? C2B C3B 1.367(5) . ? C3B C4B 1.377(5) . ? C4B C5B 1.377(5) . ? C5B C6B 1.389(4) . ? C1C C6C 1.372(4) . ? C1C C2C 1.393(4) . ? C2C C3C 1.380(5) . ? C3C C4C 1.366(5) . ? C4C C5C 1.371(5) . ? C5C C6C 1.360(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Pd1 P1 91.35(9) . . ? C1 Pd1 Br2 87.37(9) . . ? P1 Pd1 Br2 175.93(2) . . ? C1 Pd1 Br1 178.61(8) . . ? P1 Pd1 Br1 88.03(2) . . ? Br2 Pd1 Br1 93.335(14) . . ? C1B P1 C1A 108.29(14) . . ? C1B P1 C1C 102.17(14) . . ? C1A P1 C1C 105.37(14) . . ? C1B P1 Pd1 112.35(11) . . ? C1A P1 Pd1 112.55(10) . . ? C1C P1 Pd1 115.31(11) . . ? C1 S1 C7 92.31(14) . . ? C1 N1 C2 115.0(2) . . ? C1 N1 C8 122.7(2) . . ? C2 N1 C8 122.2(2) . . ? C1A N2 C5A 116.4(3) . . ? N1 C1 S1 111.4(2) . . ? N1 C1 Pd1 126.9(2) . . ? S1 C1 Pd1 121.61(15) . . ? C7 C2 C3 121.7(3) . . ? C7 C2 N1 111.5(2) . . ? C3 C2 N1 126.7(3) . . ? C4 C3 C2 117.0(3) . . ? C3 C4 C5 121.0(3) . . ? C6 C5 C4 122.0(3) . . ? C5 C6 C7 117.2(3) . . ? C2 C7 C6 121.0(3) . . ? C2 C7 S1 109.7(2) . . ? C6 C7 S1 129.3(3) . . ? N1 C8 C9 114.1(3) . . ? C14 C9 C10 118.6(3) . . ? C14 C9 C8 123.3(3) . . ? C10 C9 C8 118.1(3) . . ? C9 C10 C11 120.7(4) . . ? C12 C11 C10 120.1(4) . . ? C11 C12 C13 120.2(4) . . ? C12 C13 C14 119.9(4) . . ? C9 C14 C13 120.5(3) . . ? N2 C1A C2A 122.0(3) . . ? N2 C1A P1 114.2(2) . . ? C2A C1A P1 123.8(2) . . ? C1A C2A C3A 119.7(3) . . ? C4A C3A C2A 118.7(4) . . ? C5A C4A C3A 119.9(4) . . ? C4A C5A N2 123.3(4) . . ? C2B C1B C6B 119.9(3) . . ? C2B C1B P1 121.8(2) . . ? C6B C1B P1 118.0(2) . . ? C3B C2B C1B 119.5(3) . . ? C2B C3B C4B 121.4(3) . . ? C5B C4B C3B 119.6(3) . . ? C4B C5B C6B 119.7(3) . . ? C5B C6B C1B 119.9(3) . . ? C6C C1C C2C 119.7(3) . . ? C6C C1C P1 119.7(2) . . ? C2C C1C P1 120.3(2) . . ? C3C C2C C1C 119.5(3) . . ? C4C C3C C2C 120.0(3) . . ? C3C C4C C5C 119.9(3) . . ? C6C C5C C4C 121.0(3) . . ? C5C C6C C1C 119.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.917 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.109 # Attachment 'complex_8.cif' data_5425 _database_code_depnum_ccdc_archive 'CCDC 658820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 Br2 Cl3 N2 P Pd S' _chemical_formula_weight 826.11 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 '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' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.4169(9) _cell_length_b 18.4151(14) _cell_length_c 16.1271(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.276(2) _cell_angle_gamma 90.00 _cell_volume 3219.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4438 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.36 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 3.443 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.3397 _exptl_absorpt_correction_T_max 0.8746 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 'CCD area detector' _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 22528 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7378 _reflns_number_gt 5646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7378 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.23374(2) 0.205552(12) 0.785174(15) 0.02357(7) Uani 1 1 d . . . Br1 Br 0.16481(3) 0.297612(17) 0.66763(2) 0.03778(10) Uani 1 1 d . . . Br2 Br 0.41048(3) 0.17392(2) 0.73547(3) 0.04453(11) Uani 1 1 d . . . P1 P 0.06634(8) 0.23020(4) 0.82741(6) 0.02903(19) Uani 1 1 d . . . S1 S 0.37423(8) 0.16299(4) 0.98337(5) 0.03008(18) Uani 1 1 d . . . N1 N 0.2799(2) 0.06266(13) 0.87701(16) 0.0260(6) Uani 1 1 d . . . C1 C 0.2940(3) 0.13417(16) 0.8801(2) 0.0252(7) Uani 1 1 d . . . C2 C 0.3257(3) 0.02747(16) 0.9583(2) 0.0263(7) Uani 1 1 d . . . C3 C 0.3180(3) -0.04632(17) 0.9746(2) 0.0343(8) Uani 1 1 d . . . H3 H 0.2800 -0.0791 0.9295 0.041 Uiso 1 1 calc R . . C4 C 0.3684(3) -0.06921(17) 1.0596(2) 0.0384(8) Uani 1 1 d . . . H4 H 0.3640 -0.1187 1.0725 0.046 Uiso 1 1 calc R . . C5 C 0.4254(3) -0.02191(19) 1.1263(2) 0.0400(9) Uani 1 1 d . . . H5 H 0.4594 -0.0399 1.1833 0.048 Uiso 1 1 calc R . . C6 C 0.4333(3) 0.05155(18) 1.1107(2) 0.0342(8) Uani 1 1 d . . . H6 H 0.4721 0.0839 1.1561 0.041 Uiso 1 1 calc R . . C7 C 0.3817(3) 0.07565(16) 1.0252(2) 0.0280(7) Uani 1 1 d . . . C8 C 0.2190(3) 0.02219(17) 0.7968(2) 0.0353(8) Uani 1 1 d . . . H8A H 0.2663 -0.0220 0.7959 0.042 Uiso 1 1 calc R . . H8B H 0.2193 0.0518 0.7464 0.042 Uiso 1 1 calc R . . C9 C 0.0882(4) 0.0016(2) 0.7880(3) 0.0469(9) Uani 1 1 d . . . H9A H 0.0378 0.0456 0.7814 0.056 Uiso 1 1 calc R . . H9B H 0.0859 -0.0236 0.8410 0.056 Uiso 1 1 calc R . . C10 C 0.0346(5) -0.0476(2) 0.7092(3) 0.0719(14) Uani 1 1 d . . . H10A H 0.0399 -0.0234 0.6570 0.108 Uiso 1 1 calc R . . H10B H -0.0510 -0.0580 0.7028 0.108 Uiso 1 1 calc R . . H10C H 0.0810 -0.0926 0.7176 0.108 Uiso 1 1 calc R . . C1A C 0.0633(3) 0.19778(17) 0.9343(2) 0.0336(8) Uani 1 1 d . . . C2A C 0.0498(4) 0.2432(2) 0.9983(3) 0.0581(12) Uani 1 1 d . . . H1A H 0.0426 0.2936 0.9891 0.070 Uiso 1 1 calc R . . C3A C 0.0470(6) 0.2135(3) 1.0765(3) 0.0774(16) Uani 1 1 d . . . H2A H 0.0348 0.2433 1.1204 0.093 Uiso 1 1 calc R . . C4A C 0.0623(5) 0.1403(2) 1.0888(3) 0.0674(14) Uani 1 1 d . . . H3A H 0.0633 0.1189 1.1419 0.081 Uiso 1 1 calc R . . C5A C 0.0761(4) 0.0987(2) 1.0218(3) 0.0511(10) Uani 1 1 d . . . H4A H 0.0854 0.0483 1.0303 0.061 Uiso 1 1 calc R . . N2 N 0.0773(3) 0.12579(15) 0.9454(2) 0.0407(7) Uani 1 1 d . . . C1B C 0.0427(4) 0.32761(17) 0.8340(2) 0.0368(8) Uani 1 1 d . . . C2B C -0.0731(4) 0.3589(2) 0.8116(3) 0.0474(10) Uani 1 1 d . . . H2B H -0.1441 0.3304 0.7886 0.057 Uiso 1 1 calc R . . C3B C -0.0831(5) 0.4330(2) 0.8235(3) 0.0591(12) Uani 1 1 d . . . H3B H -0.1615 0.4547 0.8090 0.071 Uiso 1 1 calc R . . C4B C 0.0209(5) 0.4748(2) 0.8565(3) 0.0601(12) Uani 1 1 d . . . H4B H 0.0131 0.5250 0.8641 0.072 Uiso 1 1 calc R . . C5B C 0.1351(4) 0.4442(2) 0.8782(3) 0.0564(11) Uani 1 1 d . . . H5B H 0.2058 0.4731 0.9009 0.068 Uiso 1 1 calc R . . C6B C 0.1468(4) 0.37007(19) 0.8666(3) 0.0461(9) Uani 1 1 d . . . H6B H 0.2255 0.3488 0.8810 0.055 Uiso 1 1 calc R . . C1C C -0.0734(3) 0.18992(18) 0.7539(2) 0.0353(8) Uani 1 1 d . . . C2C C -0.1718(4) 0.1709(2) 0.7816(3) 0.0574(11) Uani 1 1 d . . . H2C H -0.1703 0.1818 0.8388 0.069 Uiso 1 1 calc R . . C3C C -0.2735(4) 0.1356(3) 0.7250(4) 0.0721(15) Uani 1 1 d . . . H3C H -0.3402 0.1228 0.7444 0.087 Uiso 1 1 calc R . . C4C C -0.2770(4) 0.1196(3) 0.6424(3) 0.0702(14) Uani 1 1 d . . . H4C H -0.3461 0.0956 0.6048 0.084 Uiso 1 1 calc R . . C5C C -0.1815(4) 0.1380(3) 0.6135(3) 0.0694(14) Uani 1 1 d . . . H5C H -0.1845 0.1271 0.5559 0.083 Uiso 1 1 calc R . . C6C C -0.0788(4) 0.1731(2) 0.6694(3) 0.0507(10) Uani 1 1 d . . . H6C H -0.0125 0.1855 0.6494 0.061 Uiso 1 1 calc R . . C1S C 0.1804(4) 0.1604(2) 0.5073(3) 0.0560(11) Uani 1 1 d . . . H1S H 0.2170 0.1919 0.5587 0.067 Uiso 1 1 calc R . . Cl1A Cl 0.08724(14) 0.09473(8) 0.53435(9) 0.0813(4) Uani 1 1 d . . . Cl1B Cl 0.29948(14) 0.11535(7) 0.48081(10) 0.0822(4) Uani 1 1 d . . . Cl1C Cl 0.09568(16) 0.21383(6) 0.42066(9) 0.0890(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pd1 0.02878(13) 0.02109(12) 0.02282(13) 0.00401(9) 0.01093(10) 0.00181(9) Br1 0.0508(2) 0.03122(18) 0.0339(2) 0.01200(15) 0.01707(17) 0.00934(15) Br2 0.0421(2) 0.0537(2) 0.0473(2) 0.02010(18) 0.02782(19) 0.01651(17) P1 0.0358(5) 0.0263(4) 0.0294(5) 0.0026(3) 0.0165(4) 0.0045(3) S1 0.0393(5) 0.0229(4) 0.0260(4) 0.0018(3) 0.0073(4) -0.0030(3) N1 0.0360(15) 0.0207(12) 0.0227(14) 0.0015(10) 0.0111(12) -0.0008(11) C1 0.0289(16) 0.0266(15) 0.0245(17) 0.0001(13) 0.0146(14) 0.0005(13) C2 0.0329(17) 0.0233(15) 0.0263(17) 0.0068(13) 0.0143(14) 0.0032(13) C3 0.049(2) 0.0247(16) 0.0344(19) 0.0013(14) 0.0201(17) 0.0032(15) C4 0.054(2) 0.0235(17) 0.045(2) 0.0128(16) 0.0261(19) 0.0066(16) C5 0.049(2) 0.043(2) 0.031(2) 0.0132(16) 0.0149(17) 0.0075(17) C6 0.043(2) 0.0351(18) 0.0264(18) 0.0020(14) 0.0138(16) -0.0031(15) C7 0.0337(18) 0.0232(15) 0.0283(18) 0.0043(13) 0.0115(14) 0.0009(13) C8 0.056(2) 0.0244(16) 0.0254(18) -0.0006(13) 0.0124(16) -0.0038(15) C9 0.055(2) 0.042(2) 0.039(2) -0.0077(17) 0.0077(19) -0.0094(18) C10 0.083(4) 0.069(3) 0.054(3) -0.021(2) 0.007(3) -0.034(3) C1A 0.0403(19) 0.0341(18) 0.033(2) 0.0027(14) 0.0215(16) 0.0029(14) C2A 0.103(4) 0.039(2) 0.047(2) -0.0056(19) 0.046(3) 0.001(2) C3A 0.135(5) 0.066(3) 0.052(3) -0.006(2) 0.060(3) -0.006(3) C4A 0.107(4) 0.060(3) 0.048(3) 0.001(2) 0.044(3) -0.020(3) C5A 0.069(3) 0.040(2) 0.049(3) 0.0080(18) 0.025(2) -0.0100(19) N2 0.055(2) 0.0347(16) 0.0383(18) 0.0012(14) 0.0228(15) -0.0028(14) C1B 0.055(2) 0.0290(17) 0.037(2) 0.0068(15) 0.0301(18) 0.0090(16) C2B 0.061(3) 0.040(2) 0.055(3) 0.0104(19) 0.038(2) 0.0117(19) C3B 0.079(3) 0.045(2) 0.070(3) 0.017(2) 0.047(3) 0.032(2) C4B 0.102(4) 0.035(2) 0.061(3) 0.007(2) 0.049(3) 0.017(2) C5B 0.084(3) 0.035(2) 0.053(3) -0.0060(19) 0.026(2) 0.004(2) C6B 0.059(3) 0.036(2) 0.046(2) -0.0033(17) 0.020(2) 0.0057(18) C1C 0.0296(18) 0.0358(18) 0.042(2) 0.0083(16) 0.0139(16) 0.0028(14) C2C 0.040(2) 0.082(3) 0.056(3) 0.012(2) 0.023(2) -0.001(2) C3C 0.036(2) 0.098(4) 0.086(4) 0.022(3) 0.025(3) -0.009(2) C4C 0.043(3) 0.092(4) 0.064(3) 0.020(3) 0.000(2) -0.025(2) C5C 0.051(3) 0.102(4) 0.050(3) -0.003(3) 0.008(2) -0.025(3) C6C 0.041(2) 0.067(3) 0.044(2) -0.001(2) 0.0130(19) -0.0123(19) C1S 0.080(3) 0.047(2) 0.048(3) -0.0064(19) 0.031(2) 0.004(2) Cl1A 0.0946(10) 0.0866(9) 0.0777(9) -0.0054(7) 0.0487(8) -0.0149(7) Cl1B 0.0929(10) 0.0867(9) 0.0861(10) -0.0014(7) 0.0554(8) 0.0098(7) Cl1C 0.1402(13) 0.0496(7) 0.0672(9) -0.0009(6) 0.0181(9) 0.0204(7) _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 C1 1.971(3) . ? Pd1 P1 2.2670(8) . ? Pd1 Br2 2.4633(4) . ? Pd1 Br1 2.4802(4) . ? P1 C1C 1.821(4) . ? P1 C1B 1.822(3) . ? P1 C1A 1.835(3) . ? S1 C1 1.714(3) . ? S1 C7 1.736(3) . ? N1 C1 1.326(4) . ? N1 C2 1.408(4) . ? N1 C8 1.465(4) . ? C2 C7 1.388(4) . ? C2 C3 1.392(4) . ? C3 C4 1.375(5) . ? C4 C5 1.378(5) . ? C5 C6 1.384(5) . ? C6 C7 1.391(4) . ? C8 C9 1.503(5) . ? C9 C10 1.523(5) . ? C1A N2 1.341(4) . ? C1A C2A 1.373(5) . ? C2A C3A 1.384(6) . ? C3A C4A 1.366(6) . ? C4A C5A 1.373(6) . ? C5A N2 1.333(4) . ? C1B C6B 1.382(5) . ? C1B C2B 1.382(5) . ? C2B C3B 1.388(5) . ? C3B C4B 1.375(6) . ? C4B C5B 1.362(6) . ? C5B C6B 1.390(5) . ? C1C C2C 1.378(5) . ? C1C C6C 1.379(5) . ? C2C C3C 1.392(6) . ? C3C C4C 1.352(7) . ? C4C C5C 1.358(6) . ? C5C C6C 1.394(6) . ? C1S Cl1C 1.734(5) . ? C1S Cl1A 1.754(4) . ? C1S Cl1B 1.756(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 C1 Pd1 P1 91.27(9) . . ? C1 Pd1 Br2 88.45(8) . . ? P1 Pd1 Br2 177.35(3) . . ? C1 Pd1 Br1 178.02(9) . . ? P1 Pd1 Br1 89.85(2) . . ? Br2 Pd1 Br1 90.507(14) . . ? C1C P1 C1B 108.88(17) . . ? C1C P1 C1A 102.04(16) . . ? C1B P1 C1A 102.64(15) . . ? C1C P1 Pd1 111.82(12) . . ? C1B P1 Pd1 111.65(11) . . ? C1A P1 Pd1 118.90(11) . . ? C1 S1 C7 92.10(15) . . ? C1 N1 C2 114.6(3) . . ? C1 N1 C8 123.8(3) . . ? C2 N1 C8 121.5(2) . . ? N1 C1 S1 111.4(2) . . ? N1 C1 Pd1 128.7(2) . . ? S1 C1 Pd1 119.89(16) . . ? C7 C2 C3 121.2(3) . . ? C7 C2 N1 112.0(3) . . ? C3 C2 N1 126.7(3) . . ? C4 C3 C2 117.1(3) . . ? C3 C4 C5 122.1(3) . . ? C4 C5 C6 121.2(3) . . ? C5 C6 C7 117.4(3) . . ? C2 C7 C6 121.0(3) . . ? C2 C7 S1 109.6(2) . . ? C6 C7 S1 129.4(3) . . ? N1 C8 C9 113.2(3) . . ? C8 C9 C10 110.8(3) . . ? N2 C1A C2A 122.6(3) . . ? N2 C1A P1 114.2(2) . . ? C2A C1A P1 123.2(3) . . ? C1A C2A C3A 119.0(4) . . ? C4A C3A C2A 118.9(4) . . ? C3A C4A C5A 118.5(4) . . ? N2 C5A C4A 123.8(4) . . ? C5A N2 C1A 117.3(3) . . ? C6B C1B C2B 120.1(3) . . ? C6B C1B P1 117.0(3) . . ? C2B C1B P1 122.9(3) . . ? C1B C2B C3B 119.2(4) . . ? C4B C3B C2B 120.4(4) . . ? C5B C4B C3B 120.6(4) . . ? C4B C5B C6B 119.8(4) . . ? C1B C6B C5B 120.0(4) . . ? C2C C1C C6C 118.3(4) . . ? C2C C1C P1 122.0(3) . . ? C6C C1C P1 119.6(3) . . ? C1C C2C C3C 120.2(4) . . ? C4C C3C C2C 120.6(4) . . ? C3C C4C C5C 120.3(4) . . ? C4C C5C C6C 119.8(5) . . ? C1C C6C C5C 120.8(4) . . ? Cl1C C1S Cl1A 111.3(3) . . ? Cl1C C1S Cl1B 110.5(2) . . ? Cl1A C1S Cl1B 108.1(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.691 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.098 # Attachment 'salt_A.cif' data_4298 _database_code_depnum_ccdc_archive 'CCDC 658821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 Br N O S' _chemical_formula_weight 278.21 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' S S 0.1246 0.1234 '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' O O 0.0106 0.0060 '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 8.7744(7) _cell_length_b 11.2825(9) _cell_length_c 13.2204(11) _cell_angle_alpha 95.901(2) _cell_angle_beta 97.785(2) _cell_angle_gamma 112.366(2) _cell_volume 1182.03(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3927 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 3.624 _exptl_absorpt_correction_type 'Sadabs,(Shelrick 2001)' _exptl_absorpt_correction_T_min 0.3553 _exptl_absorpt_correction_T_max 0.4767 _exptl_absorpt_process_details ? _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 'CCD area detector' _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 8290 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5406 _reflns_number_gt 4475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.5422P] 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 5406 _refine_ls_number_parameters 301 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.74745(4) 0.88600(3) 0.53589(3) 0.03662(12) Uani 1 1 d . . . Br2 Br 0.69295(5) 0.14374(4) 0.19564(3) 0.04811(14) Uani 1 1 d . . . S1 S 0.99145(14) 0.03079(9) 0.77142(7) 0.0468(2) Uani 1 1 d . . . S2 S -0.25804(10) 0.18950(8) 0.52745(7) 0.0371(2) Uani 1 1 d . . . N1 N 0.8436(3) 0.1305(3) 0.8829(2) 0.0376(6) Uani 1 1 d . B . N2 N 0.0422(3) 0.3475(2) 0.5993(2) 0.0285(5) Uani 1 1 d . D . C1 C 0.8269(5) 0.0668(3) 0.7901(3) 0.0403(8) Uani 1 1 d . . . H1 H 0.7319 0.0436 0.7390 0.048 Uiso 1 1 calc R . . C2 C 0.9957(4) 0.1554(3) 0.9470(2) 0.0347(7) Uani 1 1 d . . . C3 C 1.0499(5) 0.2190(4) 1.0501(3) 0.0439(8) Uani 1 1 d . . . H3 H 0.9834 0.2506 1.0841 0.053 Uiso 1 1 calc R . . C4 C 1.2058(5) 0.2326(4) 1.0988(3) 0.0452(9) Uani 1 1 d . . . H4 H 1.2455 0.2745 1.1673 0.054 Uiso 1 1 calc R . . C5 C 1.3056(5) 0.1856(4) 1.0487(3) 0.0462(9) Uani 1 1 d . . . H5 H 1.4107 0.1972 1.0841 0.055 Uiso 1 1 calc R . . C6 C 1.2520(5) 0.1222(4) 0.9476(3) 0.0465(9) Uani 1 1 d . . . H6 H 1.3183 0.0901 0.9140 0.056 Uiso 1 1 calc R . . C7 C 1.0940(5) 0.1082(3) 0.8976(3) 0.0371(7) Uani 1 1 d . . . C8 C 0.7174(5) 0.1770(4) 0.9137(3) 0.0562(11) Uani 1 1 d DU . . H8A H 0.7120 0.1711 0.9859 0.067 Uiso 1 1 calc R A 1 H8B H 0.6076 0.1228 0.8723 0.067 Uiso 1 1 calc R A 1 H8C H 0.6247 0.1496 0.8554 0.067 Uiso 1 1 d R A 2 H8D H 0.6741 0.1331 0.9695 0.067 Uiso 1 1 d R A 2 C9 C 0.7661(11) 0.3199(7) 0.8975(9) 0.062(3) Uani 0.55 1 d PDU B 1 H9A H 0.8800 0.3700 0.9348 0.075 Uiso 0.55 1 calc PR B 1 H9B H 0.7676 0.3222 0.8245 0.075 Uiso 0.55 1 calc PR B 1 C10 C 0.6560(12) 0.3902(10) 0.9304(9) 0.077(3) Uani 0.55 1 d PD B 1 H10A H 0.7016 0.4780 0.9176 0.115 Uiso 0.55 1 calc PR B 1 H10B H 0.6541 0.3907 1.0028 0.115 Uiso 0.55 1 calc PR B 1 H10C H 0.5439 0.3456 0.8912 0.115 Uiso 0.55 1 calc PR B 1 C11 C -0.0517(4) 0.2249(3) 0.5569(3) 0.0324(6) Uani 1 1 d . . . H11 H -0.0069 0.1634 0.5444 0.039 Uiso 1 1 calc R . . C12 C -0.0513(4) 0.4229(3) 0.6096(2) 0.0279(6) Uani 1 1 d . . . C13 C 0.0105(4) 0.5550(3) 0.6496(2) 0.0329(6) Uani 1 1 d . . . H13 H 0.1246 0.6041 0.6734 0.039 Uiso 1 1 calc R . . C14 C -0.1054(5) 0.6095(3) 0.6524(3) 0.0411(8) Uani 1 1 d . . . H14 H -0.0683 0.6977 0.6781 0.049 Uiso 1 1 calc R . . C15 C -0.2770(5) 0.5364(4) 0.6178(3) 0.0500(10) Uani 1 1 d . . . H15 H -0.3517 0.5764 0.6214 0.060 Uiso 1 1 calc R . . C16 C -0.3375(5) 0.4052(4) 0.5781(3) 0.0453(9) Uani 1 1 d . . . H16 H -0.4518 0.3559 0.5557 0.054 Uiso 1 1 calc R . . C17 C -0.2216(4) 0.3499(3) 0.5731(2) 0.0312(6) Uani 1 1 d . . . C18 C 0.2248(4) 0.3958(4) 0.6360(3) 0.0452(9) Uani 1 1 d DU . . H18A H 0.2807 0.4807 0.6175 0.054 Uiso 1 1 calc R C 1 H18B H 0.2679 0.3368 0.6041 0.054 Uiso 1 1 calc R C 1 H18C H 0.2702 0.3626 0.5821 0.054 Uiso 1 1 d R C 2 H18D H 0.2702 0.4896 0.6408 0.054 Uiso 1 1 d R C 2 C19 C 0.2586(9) 0.4052(8) 0.7558(6) 0.047(2) Uani 0.55 1 d PDU D 1 H19A H 0.2274 0.4729 0.7856 0.057 Uiso 0.55 1 calc PR D 1 H19B H 0.1839 0.3239 0.7722 0.057 Uiso 0.55 1 calc PR D 1 C20 C 0.4370(9) 0.4329(9) 0.8101(7) 0.063(2) Uani 0.55 1 d PDU D 1 H20A H 0.4407 0.4361 0.8833 0.094 Uiso 0.55 1 calc PR D 1 H20B H 0.5129 0.5149 0.7973 0.094 Uiso 0.55 1 calc PR D 1 H20C H 0.4693 0.3652 0.7838 0.094 Uiso 0.55 1 calc PR D 1 O1S O 0.4982(4) 0.7078(3) 0.6807(2) 0.0469(6) Uani 1 1 d D . . H1SA H 0.547(5) 0.759(4) 0.637(3) 0.050 Uiso 1 1 d D . . H1SB H 0.468(5) 0.752(4) 0.728(3) 0.050 Uiso 1 1 d D . . O2S O 0.5363(6) 0.8936(5) 0.3094(3) 0.0986(16) Uani 1 1 d D . . H2SA H 0.578(5) 0.969(2) 0.286(3) 0.050 Uiso 1 1 d D . . H2SB H 0.631(4) 0.891(5) 0.291(4) 0.050 Uiso 1 1 d D . . C9A C 0.7721(15) 0.3177(8) 0.9477(7) 0.052(3) Uani 0.45 1 d PDU B 2 H9A1 H 0.8658 0.3503 1.0057 0.063 Uiso 0.45 1 calc PR B 2 H9A2 H 0.6811 0.3381 0.9670 0.063 Uiso 0.45 1 calc PR B 2 C10A C 0.8244(14) 0.3734(11) 0.8517(9) 0.060(3) Uani 0.45 1 d PD B 2 H10D H 0.8642 0.4664 0.8660 0.091 Uiso 0.45 1 calc PR B 2 H10E H 0.7297 0.3393 0.7955 0.091 Uiso 0.45 1 calc PR B 2 H10F H 0.9123 0.3497 0.8331 0.091 Uiso 0.45 1 calc PR B 2 C19A C 0.2918(12) 0.3682(10) 0.7327(7) 0.051(3) Uani 0.45 1 d PDU D 2 H19C H 0.4133 0.4011 0.7435 0.061 Uiso 0.45 1 calc PR D 2 H19D H 0.2471 0.2753 0.7332 0.061 Uiso 0.45 1 calc PR D 2 C20A C 0.2364(12) 0.4373(10) 0.8154(7) 0.050(2) Uani 0.45 1 d PDU D 2 H20D H 0.2757 0.4220 0.8822 0.075 Uiso 0.45 1 calc PR D 2 H20E H 0.1161 0.4047 0.8025 0.075 Uiso 0.45 1 calc PR D 2 H20F H 0.2824 0.5289 0.8139 0.075 Uiso 0.45 1 calc PR D 2 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 Br1 0.0393(2) 0.02925(18) 0.0393(2) 0.00123(13) 0.00785(14) 0.01259(14) Br2 0.0486(2) 0.0425(2) 0.0486(2) -0.00246(16) 0.01614(17) 0.01350(17) S1 0.0623(6) 0.0448(5) 0.0302(4) -0.0039(4) 0.0010(4) 0.0233(5) S2 0.0325(4) 0.0276(4) 0.0435(5) -0.0072(3) -0.0005(3) 0.0096(3) N1 0.0329(14) 0.0386(15) 0.0302(14) 0.0030(11) 0.0061(11) 0.0029(12) N2 0.0259(12) 0.0250(12) 0.0325(13) 0.0033(10) 0.0077(10) 0.0078(10) C1 0.0444(19) 0.0369(17) 0.0293(16) 0.0038(13) 0.0020(14) 0.0070(15) C2 0.0348(16) 0.0276(15) 0.0290(16) 0.0034(12) 0.0051(12) -0.0006(13) C3 0.0369(18) 0.049(2) 0.0310(17) -0.0050(15) 0.0094(14) 0.0025(16) C4 0.0430(19) 0.0428(19) 0.0300(17) -0.0012(14) 0.0011(14) -0.0006(16) C5 0.049(2) 0.0416(19) 0.041(2) 0.0037(15) -0.0029(16) 0.0159(17) C6 0.056(2) 0.042(2) 0.043(2) 0.0013(16) 0.0017(17) 0.0263(18) C7 0.051(2) 0.0313(16) 0.0273(15) 0.0047(12) 0.0047(14) 0.0152(15) C8 0.0280(17) 0.082(3) 0.041(2) -0.0088(19) 0.0056(15) 0.0079(18) C9 0.038(4) 0.074(6) 0.064(6) -0.030(5) -0.007(5) 0.026(4) C10 0.067(6) 0.069(6) 0.104(8) 0.016(5) 0.018(5) 0.037(5) C11 0.0343(16) 0.0258(14) 0.0375(17) 0.0036(12) 0.0108(13) 0.0115(13) C12 0.0310(14) 0.0274(14) 0.0252(14) 0.0036(11) 0.0064(11) 0.0114(12) C13 0.0378(16) 0.0255(14) 0.0315(16) 0.0005(12) 0.0056(13) 0.0097(13) C14 0.052(2) 0.0301(16) 0.0414(19) -0.0039(14) 0.0013(16) 0.0220(16) C15 0.053(2) 0.050(2) 0.051(2) -0.0103(17) -0.0053(17) 0.0344(19) C16 0.0341(17) 0.047(2) 0.050(2) -0.0099(16) -0.0064(15) 0.0196(16) C17 0.0328(15) 0.0292(15) 0.0286(15) -0.0020(12) 0.0015(12) 0.0124(13) C18 0.0288(16) 0.0346(16) 0.071(2) -0.0025(15) 0.0129(15) 0.0127(13) C19 0.035(3) 0.038(3) 0.067(4) 0.022(3) -0.009(3) 0.015(3) C20 0.049(4) 0.070(5) 0.065(5) 0.007(4) 0.000(3) 0.025(4) O1S 0.0510(15) 0.0412(14) 0.0511(16) 0.0057(11) 0.0201(12) 0.0182(12) O2S 0.096(3) 0.087(3) 0.066(2) 0.029(2) -0.010(2) -0.009(3) C9A 0.047(5) 0.075(6) 0.033(5) -0.015(4) -0.002(4) 0.032(4) C10A 0.056(6) 0.062(6) 0.084(8) 0.024(6) 0.027(5) 0.038(5) C19A 0.038(4) 0.044(5) 0.080(6) 0.018(4) 0.011(4) 0.026(4) C20A 0.043(4) 0.059(5) 0.043(4) 0.023(4) 0.003(4) 0.013(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 S1 C1 1.683(4) . ? S1 C7 1.747(3) . ? S2 C11 1.678(3) . ? S2 C17 1.739(3) . ? N1 C1 1.317(4) . ? N1 C2 1.392(4) . ? N1 C8 1.479(5) . ? N2 C11 1.325(4) . ? N2 C12 1.397(4) . ? N2 C18 1.473(4) . ? C2 C7 1.374(5) . ? C2 C3 1.400(4) . ? C3 C4 1.376(5) . ? C4 C5 1.387(6) . ? C5 C6 1.378(5) . ? C6 C7 1.395(5) . ? C8 C9A 1.472(8) . ? C8 C9 1.550(8) . ? C9 C10 1.541(9) . ? C12 C17 1.390(4) . ? C12 C13 1.394(4) . ? C13 C14 1.377(5) . ? C14 C15 1.395(6) . ? C15 C16 1.384(5) . ? C16 C17 1.385(5) . ? C18 C19A 1.448(8) . ? C18 C19 1.556(8) . ? C19 C20 1.529(8) . ? C9A C10A 1.522(9) . ? C19A C20A 1.515(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C7 89.76(18) . . ? C11 S2 C17 90.41(15) . . ? C1 N1 C2 113.2(3) . . ? C1 N1 C8 123.2(3) . . ? C2 N1 C8 123.5(3) . . ? C11 N2 C12 112.9(3) . . ? C11 N2 C18 122.8(3) . . ? C12 N2 C18 124.3(3) . . ? N1 C1 S1 114.6(3) . . ? C7 C2 N1 111.8(3) . . ? C7 C2 C3 121.2(3) . . ? N1 C2 C3 127.0(3) . . ? C4 C3 C2 117.0(4) . . ? C3 C4 C5 121.9(3) . . ? C6 C5 C4 121.2(4) . . ? C5 C6 C7 117.2(4) . . ? C2 C7 C6 121.5(3) . . ? C2 C7 S1 110.7(3) . . ? C6 C7 S1 127.8(3) . . ? C9A C8 N1 117.5(5) . . ? C9A C8 C9 25.1(4) . . ? N1 C8 C9 109.6(4) . . ? C10 C9 C8 118.2(8) . . ? N2 C11 S2 114.6(2) . . ? C17 C12 C13 121.6(3) . . ? C17 C12 N2 111.6(3) . . ? C13 C12 N2 126.8(3) . . ? C14 C13 C12 116.8(3) . . ? C13 C14 C15 122.0(3) . . ? C16 C15 C14 120.9(3) . . ? C15 C16 C17 117.7(3) . . ? C16 C17 C12 121.1(3) . . ? C16 C17 S2 128.5(3) . . ? C12 C17 S2 110.5(2) . . ? C19A C18 N2 120.7(5) . . ? C19A C18 C19 25.2(4) . . ? N2 C18 C19 108.2(4) . . ? C20 C19 C18 117.9(7) . . ? C8 C9A C10A 102.6(7) . . ? C18 C19A C20A 105.0(6) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.027 _refine_diff_density_min -0.754 _refine_diff_density_rms 0.114