# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cl Cu O2 S2' _chemical_formula_sum 'C18 H20 Cl Cu O2 S2' _chemical_formula_weight 431.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' Cu Cu 0.3201 1.2651 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 11.4008(14) _cell_length_b 9.6644(11) _cell_length_c 16.7665(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.393(3) _cell_angle_gamma 90.00 _cell_volume 1835.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2323 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 24.56 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.570 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7442 _exptl_absorpt_correction_T_max 0.8847 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10261 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3602 _reflns_number_gt 2245 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0660P)^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 3602 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.08519(5) 0.55591(6) 0.07449(3) 0.0348(2) Uani 1 1 d . . . Cl1 Cl 0.89350(10) 0.62445(12) 0.02383(7) 0.0335(3) Uani 1 1 d . . . S1 S 1.06799(11) 0.42293(13) 0.18808(7) 0.0330(3) Uani 1 1 d . . . S2 S 1.27117(11) 0.21396(13) 0.42956(7) 0.0349(3) Uani 1 1 d . . . O1 O 0.9161(3) 0.1617(4) 0.4286(2) 0.0497(10) Uani 1 1 d . . . O2 O 0.8837(3) 0.2465(4) 0.2992(2) 0.0424(9) Uani 1 1 d . . . C1 C 0.8324(5) 0.2195(7) 0.3698(3) 0.0527(16) Uani 1 1 d . . . H1A H 0.7669 0.1559 0.3582 0.063 Uiso 1 1 calc R . . H1B H 0.8019 0.3048 0.3899 0.063 Uiso 1 1 calc R . . C2 C 0.9071(4) 0.1376(5) 0.2517(3) 0.0338(11) Uani 1 1 d . . . C3 C 0.9041(5) -0.0002(6) 0.2748(3) 0.0483(14) Uani 1 1 d . . . H3A H 0.8864 -0.0242 0.3258 0.058 Uiso 1 1 calc R . . C4 C 0.9277(6) -0.1009(6) 0.2205(4) 0.0622(18) Uani 1 1 d . . . H4A H 0.9242 -0.1935 0.2352 0.075 Uiso 1 1 calc R . . C5 C 0.9557(6) -0.0687(7) 0.1470(4) 0.0679(19) Uani 1 1 d . . . H5A H 0.9720 -0.1386 0.1117 0.081 Uiso 1 1 calc R . . C6 C 0.9602(5) 0.0690(7) 0.1235(3) 0.0527(15) Uani 1 1 d . . . H6A H 0.9797 0.0908 0.0726 0.063 Uiso 1 1 calc R . . C7 C 0.9359(4) 0.1746(5) 0.1760(3) 0.0344(12) Uani 1 1 d . . . C8 C 0.9380(4) 0.3208(5) 0.1493(3) 0.0405(13) Uani 1 1 d . . . H8A H 0.8684 0.3666 0.1649 0.049 Uiso 1 1 calc R . . H8B H 0.9322 0.3219 0.0912 0.049 Uiso 1 1 calc R . . C9 C 1.1917(4) 0.3059(5) 0.1877(3) 0.0388(12) Uani 1 1 d . . . H9A H 1.1636 0.2167 0.1670 0.047 Uiso 1 1 calc R . . H9B H 1.2460 0.3419 0.1522 0.047 Uiso 1 1 calc R . . C10 C 1.2566(5) 0.2868(7) 0.2708(3) 0.0643(19) Uani 1 1 d . . . H10A H 1.3259 0.2303 0.2665 0.077 Uiso 1 1 calc R . . H10B H 1.2836 0.3767 0.2911 0.077 Uiso 1 1 calc R . . C11 C 1.1870(5) 0.2226(7) 0.3297(3) 0.0626(18) Uani 1 1 d . . . H11A H 1.1643 0.1298 0.3120 0.075 Uiso 1 1 calc R . . H11B H 1.1156 0.2758 0.3328 0.075 Uiso 1 1 calc R . . C12 C 1.1576(5) 0.1324(5) 0.4826(3) 0.0439(13) Uani 1 1 d . . . H12A H 1.1095 0.0735 0.4452 0.053 Uiso 1 1 calc R . . H12B H 1.1959 0.0736 0.5246 0.053 Uiso 1 1 calc R . . C13 C 1.0790(5) 0.2314(5) 0.5191(3) 0.0378(12) Uani 1 1 d . . . C14 C 1.1242(5) 0.3114(6) 0.5850(3) 0.0516(15) Uani 1 1 d . . . H14A H 1.2037 0.3046 0.6041 0.062 Uiso 1 1 calc R . . C15 C 1.0530(6) 0.4001(6) 0.6219(4) 0.0624(17) Uani 1 1 d . . . H15A H 1.0849 0.4546 0.6646 0.075 Uiso 1 1 calc R . . C16 C 0.9332(6) 0.4081(6) 0.5953(3) 0.0571(16) Uani 1 1 d . . . H16A H 0.8841 0.4658 0.6211 0.069 Uiso 1 1 calc R . . C17 C 0.8885(5) 0.3306(6) 0.5312(3) 0.0513(15) Uani 1 1 d . . . H17A H 0.8084 0.3361 0.5132 0.062 Uiso 1 1 calc R . . C18 C 0.9598(5) 0.2446(5) 0.4927(3) 0.0382(12) 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 Cu1 0.0327(4) 0.0380(4) 0.0319(4) 0.0002(3) -0.0041(3) -0.0062(3) Cl1 0.0283(6) 0.0363(7) 0.0347(6) -0.0080(5) -0.0011(5) 0.0041(5) S1 0.0338(7) 0.0387(7) 0.0253(6) 0.0037(5) -0.0020(5) 0.0019(5) S2 0.0359(7) 0.0368(7) 0.0315(7) 0.0054(6) 0.0022(5) 0.0080(5) O1 0.042(2) 0.068(3) 0.038(2) -0.0040(19) -0.0031(17) 0.0100(19) O2 0.046(2) 0.044(2) 0.039(2) 0.0013(17) 0.0147(17) -0.0074(16) C1 0.032(3) 0.086(5) 0.041(3) 0.004(3) 0.005(3) 0.002(3) C2 0.031(3) 0.039(3) 0.031(3) 0.002(2) -0.002(2) -0.004(2) C3 0.054(4) 0.043(3) 0.046(3) 0.006(3) 0.000(3) -0.011(3) C4 0.063(4) 0.039(4) 0.079(5) -0.003(4) -0.013(4) -0.012(3) C5 0.063(4) 0.056(4) 0.080(5) -0.034(4) -0.009(4) 0.002(3) C6 0.045(3) 0.069(4) 0.042(3) -0.014(3) -0.001(3) -0.004(3) C7 0.028(3) 0.041(3) 0.033(3) 0.004(2) -0.003(2) -0.005(2) C8 0.031(3) 0.058(4) 0.032(3) 0.011(3) -0.002(2) -0.001(2) C9 0.038(3) 0.048(3) 0.030(3) 0.005(2) 0.003(2) 0.010(2) C10 0.046(4) 0.098(5) 0.048(4) 0.022(4) 0.002(3) 0.028(3) C11 0.041(3) 0.085(5) 0.060(4) 0.024(4) -0.006(3) 0.018(3) C12 0.036(3) 0.042(3) 0.054(3) 0.010(3) 0.009(3) 0.006(2) C13 0.041(3) 0.037(3) 0.035(3) 0.011(2) 0.003(2) 0.006(2) C14 0.042(3) 0.052(4) 0.058(4) 0.002(3) -0.005(3) 0.003(3) C15 0.073(5) 0.058(4) 0.056(4) -0.011(3) 0.010(3) -0.011(3) C16 0.059(4) 0.067(4) 0.048(4) -0.008(3) 0.020(3) 0.008(3) C17 0.032(3) 0.072(4) 0.053(4) 0.002(3) 0.016(3) 0.004(3) C18 0.039(3) 0.045(3) 0.032(3) 0.007(2) 0.009(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 S2 2.2460(13) 2_755 ? Cu1 S1 2.3238(13) . ? Cu1 Cl1 2.3500(13) . ? Cu1 Cl1 2.4299(13) 3_765 ? Cl1 Cu1 2.4299(13) 3_765 ? S1 C9 1.809(5) . ? S1 C8 1.838(5) . ? S2 C12 1.829(5) . ? S2 C11 1.837(6) . ? S2 Cu1 2.2459(13) 2_745 ? O1 C18 1.388(6) . ? O1 C1 1.409(6) . ? O2 C2 1.364(6) . ? O2 C1 1.402(6) . ? C2 C3 1.388(7) . ? C2 C7 1.394(6) . ? C3 C4 1.379(8) . ? C4 C5 1.344(9) . ? C5 C6 1.390(8) . ? C6 C7 1.395(7) . ? C7 C8 1.483(7) . ? C9 C10 1.515(7) . ? C10 C11 1.470(8) . ? C12 C13 1.489(7) . ? C13 C18 1.388(7) . ? C13 C14 1.399(7) . ? C14 C15 1.373(8) . ? C15 C16 1.391(9) . ? C16 C17 1.361(8) . ? C17 C18 1.373(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 S2 Cu1 S1 121.96(5) 2_755 . ? S2 Cu1 Cl1 116.69(5) 2_755 . ? S1 Cu1 Cl1 106.99(5) . . ? S2 Cu1 Cl1 109.82(5) 2_755 3_765 ? S1 Cu1 Cl1 100.56(5) . 3_765 ? Cl1 Cu1 Cl1 96.67(4) . 3_765 ? Cu1 Cl1 Cu1 83.33(4) . 3_765 ? C9 S1 C8 105.1(2) . . ? C9 S1 Cu1 101.87(16) . . ? C8 S1 Cu1 98.37(15) . . ? C12 S2 C11 97.9(3) . . ? C12 S2 Cu1 106.23(17) . 2_745 ? C11 S2 Cu1 108.2(2) . 2_745 ? C18 O1 C1 118.0(4) . . ? C2 O2 C1 118.4(4) . . ? O2 C1 O1 110.6(4) . . ? O2 C2 C3 124.4(5) . . ? O2 C2 C7 114.5(4) . . ? C3 C2 C7 121.1(5) . . ? C4 C3 C2 118.7(5) . . ? C5 C4 C3 121.7(6) . . ? C4 C5 C6 120.2(6) . . ? C5 C6 C7 120.4(6) . . ? C2 C7 C6 118.0(5) . . ? C2 C7 C8 122.2(5) . . ? C6 C7 C8 119.7(5) . . ? C7 C8 S1 116.4(3) . . ? C10 C9 S1 111.9(4) . . ? C11 C10 C9 115.1(5) . . ? C10 C11 S2 111.4(4) . . ? C13 C12 S2 114.5(4) . . ? C18 C13 C14 117.5(5) . . ? C18 C13 C12 122.7(5) . . ? C14 C13 C12 119.7(5) . . ? C15 C14 C13 121.1(6) . . ? C14 C15 C16 119.9(6) . . ? C17 C16 C15 119.3(6) . . ? C16 C17 C18 121.0(6) . . ? C17 C18 O1 122.2(5) . . ? C17 C18 C13 121.0(5) . . ? O1 C18 C13 116.7(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.889 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 950547' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H40 Br2 Cu2 O4 S4' _chemical_formula_sum 'C36 H40 Br2 Cu2 O4 S4' _chemical_formula_weight 951.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.6238(8) _cell_length_b 9.2933(4) _cell_length_c 22.3113(9) _cell_angle_alpha 90.00 _cell_angle_beta 114.138(2) _cell_angle_gamma 90.00 _cell_volume 3713.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2902 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 23.29 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.703 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 3.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5827 _exptl_absorpt_correction_T_max 0.7172 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34577 _diffrn_reflns_av_R_equivalents 0.0854 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.00 _reflns_number_total 8961 _reflns_number_gt 5540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0716P)^2^+2.2156P] 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 8961 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_restrained_S_all 0.855 _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 Cu1 Cu 0.33551(3) 0.56605(7) 0.26760(3) 0.02770(16) Uani 1 1 d . . . Cu2 Cu 0.17697(3) 0.46799(7) 0.26098(3) 0.02559(15) Uani 1 1 d . . . Br1 Br 0.21048(2) 0.66339(6) 0.19791(2) 0.02684(13) Uani 1 1 d . . . Br2 Br 0.30517(2) 0.40239(6) 0.34358(2) 0.02810(13) Uani 1 1 d . . . S1 S 0.58925(6) 0.23715(14) 0.16551(6) 0.0256(3) Uani 1 1 d . . . S2 S 0.37104(6) 0.41987(14) 0.20225(6) 0.0262(3) Uani 1 1 d . . . S3 S 0.12501(6) 0.59672(14) 0.32133(6) 0.0247(3) Uani 1 1 d . . . S4 S -0.11549(6) 0.79089(14) 0.31186(6) 0.0249(3) Uani 1 1 d . . . O1 O 0.40522(16) 0.3350(4) 0.04344(16) 0.0323(8) Uani 1 1 d . . . O2 O 0.29400(18) 0.3285(4) 0.05216(16) 0.0344(9) Uani 1 1 d . . . O3 O 0.14598(18) 0.7919(4) 0.46007(16) 0.0301(8) Uani 1 1 d . . . O4 O 0.06770(16) 0.8848(4) 0.50666(15) 0.0272(8) Uani 1 1 d . . . C1 C 0.4448(2) 0.3177(6) 0.0055(2) 0.0274(11) Uani 1 1 d . . . C2 C 0.4279(3) 0.3926(6) -0.0524(2) 0.0311(12) Uani 1 1 d . . . H2A H 0.3863 0.4561 -0.0687 0.037 Uiso 1 1 calc R . . C3 C 0.4726(3) 0.3737(6) -0.0864(3) 0.0386(14) Uani 1 1 d . . . H3A H 0.4616 0.4249 -0.1261 0.046 Uiso 1 1 calc R . . C4 C 0.5332(3) 0.2809(7) -0.0632(3) 0.0468(16) Uani 1 1 d . . . H4A H 0.5633 0.2680 -0.0870 0.056 Uiso 1 1 calc R . . C5 C 0.5494(3) 0.2070(6) -0.0048(3) 0.0407(14) Uani 1 1 d . . . H5A H 0.5912 0.1440 0.0113 0.049 Uiso 1 1 calc R . . C6 C 0.5056(3) 0.2237(6) 0.0303(2) 0.0288(11) Uani 1 1 d . . . C7 C 0.5236(3) 0.1413(6) 0.0929(2) 0.0308(12) Uani 1 1 d . . . H7A H 0.5453 0.0470 0.0896 0.037 Uiso 1 1 calc R . . H7B H 0.4768 0.1229 0.0984 0.037 Uiso 1 1 calc R . . C8 C 0.5288(2) 0.3233(5) 0.1988(2) 0.0266(11) Uani 1 1 d . . . H8A H 0.5589 0.3942 0.2322 0.032 Uiso 1 1 calc R . . H8B H 0.4897 0.3774 0.1629 0.032 Uiso 1 1 calc R . . C9 C 0.4908(3) 0.2250(6) 0.2297(3) 0.0334(12) Uani 1 1 d . . . H9A H 0.5290 0.1666 0.2643 0.040 Uiso 1 1 calc R . . H9B H 0.4572 0.1585 0.1958 0.040 Uiso 1 1 calc R . . C10 C 0.4454(3) 0.3096(6) 0.2598(2) 0.0324(12) Uani 1 1 d . . . H10A H 0.4799 0.3725 0.2949 0.039 Uiso 1 1 calc R . . H10B H 0.4233 0.2405 0.2806 0.039 Uiso 1 1 calc R . . C11 C 0.2925(2) 0.2943(6) 0.1735(2) 0.0324(12) Uani 1 1 d . . . H11A H 0.2850 0.2581 0.2121 0.039 Uiso 1 1 calc R . . H11B H 0.2469 0.3479 0.1457 0.039 Uiso 1 1 calc R . . C12 C 0.3001(2) 0.1670(6) 0.1351(2) 0.0280(11) Uani 1 1 d . . . C13 C 0.3023(3) 0.0269(6) 0.1576(3) 0.0361(13) Uani 1 1 d . . . H13A H 0.3006 0.0108 0.1990 0.043 Uiso 1 1 calc R . . C14 C 0.3070(3) -0.0890(6) 0.1211(3) 0.0381(13) Uani 1 1 d . . . H14A H 0.3095 -0.1838 0.1378 0.046 Uiso 1 1 calc R . . C15 C 0.3081(3) -0.0679(6) 0.0603(3) 0.0396(14) Uani 1 1 d . . . H15A H 0.3106 -0.1483 0.0349 0.047 Uiso 1 1 calc R . . C16 C 0.3056(3) 0.0692(6) 0.0362(3) 0.0362(13) Uani 1 1 d . . . H16A H 0.3073 0.0833 -0.0053 0.043 Uiso 1 1 calc R . . C17 C 0.3007(2) 0.1874(6) 0.0727(2) 0.0293(12) Uani 1 1 d . . . C18 C 0.3276(3) 0.3665(6) 0.0097(2) 0.0365(13) Uani 1 1 d . . . H18A H 0.3201 0.4701 -0.0013 0.044 Uiso 1 1 calc R . . H18B H 0.3056 0.3103 -0.0316 0.044 Uiso 1 1 calc R . . C19 C 0.1563(2) 0.9035(5) 0.4240(2) 0.0242(10) Uani 1 1 d . . . C20 C 0.1374(3) 1.0460(6) 0.4285(3) 0.0307(12) Uani 1 1 d . . . H20A H 0.1154 1.0717 0.4578 0.037 Uiso 1 1 calc R . . C21 C 0.1505(3) 1.1503(6) 0.3903(3) 0.0378(13) Uani 1 1 d . . . H21A H 0.1380 1.2477 0.3939 0.045 Uiso 1 1 calc R . . C22 C 0.1818(3) 1.1140(6) 0.3469(3) 0.0400(14) Uani 1 1 d . . . H22A H 0.1915 1.1860 0.3212 0.048 Uiso 1 1 calc R . . C23 C 0.1990(3) 0.9700(7) 0.3415(2) 0.0359(13) Uani 1 1 d . . . H23A H 0.2198 0.9444 0.3112 0.043 Uiso 1 1 calc R . . C24 C 0.1863(2) 0.8636(5) 0.3794(2) 0.0249(11) Uani 1 1 d . . . C25 C 0.2051(2) 0.7100(6) 0.3710(2) 0.0312(12) Uani 1 1 d . . . H25A H 0.2303 0.6658 0.4150 0.037 Uiso 1 1 calc R . . H25B H 0.2412 0.7100 0.3503 0.037 Uiso 1 1 calc R . . C26 C 0.0629(2) 0.7161(5) 0.2574(2) 0.0268(11) Uani 1 1 d . . . H26A H 0.0939 0.7856 0.2459 0.032 Uiso 1 1 calc R . . H26B H 0.0350 0.6578 0.2178 0.032 Uiso 1 1 calc R . . C27 C 0.0064(2) 0.8010(5) 0.2750(2) 0.0270(11) Uani 1 1 d . . . H27A H 0.0334 0.8738 0.3088 0.032 Uiso 1 1 calc R . . H27B H -0.0284 0.8526 0.2355 0.032 Uiso 1 1 calc R . . C28 C -0.0384(2) 0.7039(5) 0.3007(2) 0.0288(11) Uani 1 1 d . . . H28A H -0.0040 0.6632 0.3434 0.035 Uiso 1 1 calc R . . H28B H -0.0585 0.6226 0.2698 0.035 Uiso 1 1 calc R . . C29 C -0.0668(3) 0.8745(5) 0.3915(2) 0.0285(11) Uani 1 1 d . . . H29A H -0.0185 0.9128 0.3942 0.034 Uiso 1 1 calc R . . H29B H -0.0967 0.9568 0.3953 0.034 Uiso 1 1 calc R . . C30 C -0.0518(2) 0.7736(5) 0.4489(2) 0.0250(11) Uani 1 1 d . . . C31 C -0.1050(3) 0.6772(6) 0.4499(3) 0.0318(12) Uani 1 1 d . . . H31A H -0.1504 0.6673 0.4119 0.038 Uiso 1 1 calc R . . C32 C -0.0940(3) 0.5949(6) 0.5047(3) 0.0337(12) Uani 1 1 d . . . H32A H -0.1316 0.5293 0.5038 0.040 Uiso 1 1 calc R . . C33 C -0.0289(3) 0.6072(6) 0.5605(3) 0.0372(13) Uani 1 1 d . . . H33A H -0.0214 0.5507 0.5982 0.045 Uiso 1 1 calc R . . C34 C 0.0259(3) 0.7033(6) 0.5613(2) 0.0312(12) Uani 1 1 d . . . H34A H 0.0708 0.7136 0.5997 0.037 Uiso 1 1 calc R . . C35 C 0.0145(2) 0.7837(5) 0.5058(2) 0.0251(11) Uani 1 1 d . . . C36 C 0.1395(2) 0.8304(6) 0.5192(2) 0.0300(12) Uani 1 1 d . . . H36A H 0.1493 0.7448 0.5480 0.036 Uiso 1 1 calc R . . H36C H 0.1774 0.9042 0.5426 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0180(3) 0.0374(4) 0.0263(3) -0.0033(3) 0.0077(2) -0.0015(3) Cu2 0.0180(3) 0.0324(4) 0.0250(3) -0.0024(3) 0.0074(2) -0.0005(3) Br1 0.0167(2) 0.0372(3) 0.0246(3) 0.0057(2) 0.00638(18) 0.0002(2) Br2 0.0166(2) 0.0370(3) 0.0275(3) 0.0062(2) 0.00582(18) 0.0007(2) S1 0.0169(5) 0.0360(8) 0.0227(6) 0.0013(5) 0.0069(4) 0.0019(5) S2 0.0173(5) 0.0361(8) 0.0249(6) -0.0024(5) 0.0084(5) 0.0007(5) S3 0.0167(5) 0.0332(7) 0.0235(6) -0.0009(5) 0.0076(4) 0.0018(5) S4 0.0156(5) 0.0339(7) 0.0232(6) 0.0007(5) 0.0058(4) 0.0033(5) O1 0.0185(15) 0.052(2) 0.0226(18) 0.0067(17) 0.0042(13) 0.0054(16) O2 0.0256(17) 0.046(2) 0.031(2) 0.0038(18) 0.0108(15) 0.0046(17) O3 0.0340(18) 0.032(2) 0.0282(19) 0.0001(16) 0.0167(15) 0.0016(16) O4 0.0190(15) 0.034(2) 0.0276(19) -0.0032(15) 0.0087(14) -0.0018(15) C1 0.020(2) 0.036(3) 0.023(3) -0.004(2) 0.0060(19) -0.005(2) C2 0.026(2) 0.039(3) 0.021(3) 0.001(2) 0.002(2) -0.003(2) C3 0.046(3) 0.038(3) 0.027(3) -0.004(2) 0.010(2) -0.017(3) C4 0.036(3) 0.074(5) 0.035(3) -0.009(3) 0.019(3) -0.003(3) C5 0.032(3) 0.056(4) 0.034(3) 0.000(3) 0.013(2) 0.008(3) C6 0.026(2) 0.035(3) 0.023(3) -0.001(2) 0.007(2) -0.002(2) C7 0.024(2) 0.040(3) 0.023(3) -0.002(2) 0.004(2) -0.002(2) C8 0.021(2) 0.031(3) 0.028(3) 0.000(2) 0.010(2) 0.004(2) C9 0.024(2) 0.041(3) 0.037(3) 0.005(3) 0.015(2) 0.006(2) C10 0.023(2) 0.045(4) 0.028(3) 0.005(2) 0.009(2) 0.006(2) C11 0.021(2) 0.045(3) 0.033(3) -0.012(3) 0.013(2) -0.011(2) C12 0.0120(19) 0.041(3) 0.028(3) -0.004(2) 0.0051(18) -0.003(2) C13 0.028(3) 0.049(4) 0.034(3) -0.005(3) 0.016(2) -0.007(3) C14 0.028(3) 0.039(3) 0.046(4) -0.004(3) 0.015(2) -0.006(2) C15 0.030(3) 0.044(4) 0.045(4) -0.017(3) 0.015(2) -0.001(3) C16 0.025(2) 0.055(4) 0.028(3) -0.009(3) 0.010(2) -0.007(3) C17 0.019(2) 0.040(3) 0.027(3) -0.002(2) 0.0078(19) 0.000(2) C18 0.022(2) 0.054(4) 0.027(3) 0.009(3) 0.003(2) 0.007(2) C19 0.020(2) 0.031(3) 0.022(2) 0.000(2) 0.0085(18) -0.003(2) C20 0.023(2) 0.033(3) 0.035(3) -0.008(2) 0.010(2) 0.001(2) C21 0.031(3) 0.032(3) 0.039(3) 0.001(3) 0.002(2) -0.005(2) C22 0.040(3) 0.041(4) 0.034(3) 0.009(3) 0.010(2) -0.014(3) C23 0.024(2) 0.062(4) 0.020(3) -0.003(3) 0.006(2) -0.016(3) C24 0.018(2) 0.035(3) 0.018(2) -0.003(2) 0.0045(18) -0.004(2) C25 0.013(2) 0.052(4) 0.022(3) -0.004(2) 0.0007(18) 0.003(2) C26 0.018(2) 0.038(3) 0.021(3) 0.002(2) 0.0049(18) 0.002(2) C27 0.016(2) 0.034(3) 0.029(3) 0.003(2) 0.0077(19) 0.006(2) C28 0.022(2) 0.031(3) 0.033(3) 0.005(2) 0.011(2) 0.008(2) C29 0.024(2) 0.030(3) 0.028(3) -0.001(2) 0.007(2) 0.002(2) C30 0.020(2) 0.028(3) 0.028(3) -0.002(2) 0.0107(19) 0.004(2) C31 0.024(2) 0.037(3) 0.035(3) 0.001(2) 0.013(2) 0.002(2) C32 0.030(3) 0.035(3) 0.042(3) 0.005(3) 0.021(2) -0.001(2) C33 0.037(3) 0.042(4) 0.038(3) 0.015(3) 0.021(2) 0.007(3) C34 0.027(2) 0.042(3) 0.023(3) 0.002(2) 0.009(2) 0.005(2) C35 0.023(2) 0.030(3) 0.024(3) -0.001(2) 0.0117(19) 0.000(2) C36 0.016(2) 0.054(4) 0.018(2) 0.000(2) 0.0056(18) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 S1 2.2656(13) 2_655 ? Cu1 S2 2.2998(13) . ? Cu1 Br1 2.4771(7) . ? Cu1 Br2 2.5234(8) . ? Cu2 S4 2.2808(13) 2_545 ? Cu2 S3 2.3253(13) . ? Cu2 Br2 2.5109(7) . ? Cu2 Br1 2.5430(8) . ? S1 C8 1.822(4) . ? S1 C7 1.836(5) . ? S1 Cu1 2.2657(13) 2_645 ? S2 C10 1.816(5) . ? S2 C11 1.828(5) . ? S3 C26 1.824(5) . ? S3 C25 1.839(5) . ? S4 C29 1.812(5) . ? S4 C28 1.820(4) . ? S4 Cu2 2.2807(13) 2 ? O1 C1 1.372(5) . ? O1 C18 1.427(5) . ? O2 C17 1.378(6) . ? O2 C18 1.403(6) . ? O3 C19 1.377(6) . ? O3 C36 1.422(5) . ? O4 C35 1.399(5) . ? O4 C36 1.413(5) . ? C1 C2 1.384(7) . ? C1 C6 1.398(7) . ? C2 C3 1.384(7) . ? C3 C4 1.386(8) . ? C4 C5 1.389(8) . ? C5 C6 1.389(7) . ? C6 C7 1.503(7) . ? C8 C9 1.511(7) . ? C9 C10 1.534(6) . ? C11 C12 1.504(7) . ? C12 C13 1.390(7) . ? C12 C17 1.409(7) . ? C13 C14 1.376(7) . ? C14 C15 1.380(7) . ? C15 C16 1.375(8) . ? C16 C17 1.394(7) . ? C19 C20 1.389(7) . ? C19 C24 1.398(6) . ? C20 C21 1.383(7) . ? C21 C22 1.385(8) . ? C22 C23 1.397(8) . ? C23 C24 1.390(7) . ? C24 C25 1.506(7) . ? C26 C27 1.537(6) . ? C27 C28 1.526(6) . ? C29 C30 1.516(7) . ? C30 C31 1.383(6) . ? C30 C35 1.400(6) . ? C31 C32 1.381(7) . ? C32 C33 1.377(7) . ? C33 C34 1.393(7) . ? C34 C35 1.385(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 S1 Cu1 S2 123.18(5) 2_655 . ? S1 Cu1 Br1 111.63(4) 2_655 . ? S2 Cu1 Br1 107.28(4) . . ? S1 Cu1 Br2 104.46(4) 2_655 . ? S2 Cu1 Br2 106.61(4) . . ? Br1 Cu1 Br2 101.33(2) . . ? S4 Cu2 S3 123.67(5) 2_545 . ? S4 Cu2 Br2 115.28(4) 2_545 . ? S3 Cu2 Br2 104.17(4) . . ? S4 Cu2 Br1 107.59(4) 2_545 . ? S3 Cu2 Br1 103.12(4) . . ? Br2 Cu2 Br1 99.87(2) . . ? Cu1 Br1 Cu2 78.80(2) . . ? Cu2 Br2 Cu1 78.55(2) . . ? C8 S1 C7 103.5(2) . . ? C8 S1 Cu1 113.42(16) . 2_645 ? C7 S1 Cu1 105.89(18) . 2_645 ? C10 S2 C11 101.9(2) . . ? C10 S2 Cu1 104.43(16) . . ? C11 S2 Cu1 99.71(16) . . ? C26 S3 C25 104.8(2) . . ? C26 S3 Cu2 99.86(15) . . ? C25 S3 Cu2 100.02(15) . . ? C29 S4 C28 100.9(2) . . ? C29 S4 Cu2 107.61(17) . 2 ? C28 S4 Cu2 116.78(16) . 2 ? C1 O1 C18 116.7(4) . . ? C17 O2 C18 117.2(4) . . ? C19 O3 C36 116.2(4) . . ? C35 O4 C36 116.1(4) . . ? O1 C1 C2 122.6(4) . . ? O1 C1 C6 115.9(4) . . ? C2 C1 C6 121.5(4) . . ? C3 C2 C1 118.9(5) . . ? C2 C3 C4 120.9(5) . . ? C3 C4 C5 119.4(5) . . ? C4 C5 C6 121.0(5) . . ? C5 C6 C1 118.2(5) . . ? C5 C6 C7 120.2(5) . . ? C1 C6 C7 121.6(4) . . ? C6 C7 S1 112.7(4) . . ? C9 C8 S1 116.4(4) . . ? C8 C9 C10 111.9(4) . . ? C9 C10 S2 114.9(3) . . ? C12 C11 S2 115.8(3) . . ? C13 C12 C17 118.1(5) . . ? C13 C12 C11 121.8(4) . . ? C17 C12 C11 120.0(5) . . ? C14 C13 C12 121.3(5) . . ? C13 C14 C15 120.2(6) . . ? C16 C15 C14 120.1(5) . . ? C15 C16 C17 120.2(5) . . ? O2 C17 C16 125.2(5) . . ? O2 C17 C12 114.7(4) . . ? C16 C17 C12 120.1(5) . . ? O2 C18 O1 106.7(4) . . ? O3 C19 C20 124.7(4) . . ? O3 C19 C24 114.9(4) . . ? C20 C19 C24 120.4(5) . . ? C21 C20 C19 120.1(5) . . ? C20 C21 C22 120.5(5) . . ? C21 C22 C23 119.1(5) . . ? C24 C23 C22 121.2(5) . . ? C23 C24 C19 118.6(5) . . ? C23 C24 C25 118.9(4) . . ? C19 C24 C25 122.5(4) . . ? C24 C25 S3 115.1(3) . . ? C27 C26 S3 115.7(3) . . ? C28 C27 C26 112.3(4) . . ? C27 C28 S4 115.3(3) . . ? C30 C29 S4 113.9(4) . . ? C31 C30 C35 117.2(5) . . ? C31 C30 C29 121.8(4) . . ? C35 C30 C29 120.7(4) . . ? C32 C31 C30 121.8(5) . . ? C33 C32 C31 120.4(5) . . ? C32 C33 C34 119.4(5) . . ? C35 C34 C33 119.6(5) . . ? C34 C35 O4 120.2(4) . . ? C34 C35 C30 121.6(4) . . ? O4 C35 C30 118.0(4) . . ? O4 C36 O3 111.5(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.623 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 950548' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 Cu N O2 S3' _chemical_formula_sum 'C19 H20 Cu N O2 S3' _chemical_formula_weight 454.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.814(12) _cell_length_b 14.973(15) _cell_length_c 11.418(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.401(19) _cell_angle_gamma 90.00 _cell_volume 1947(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 958 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.76 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.457 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8004 _exptl_absorpt_correction_T_max 0.8562 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11022 _diffrn_reflns_av_R_equivalents 0.1731 _diffrn_reflns_av_sigmaI/netI 0.1852 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3689 _reflns_number_gt 1895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0555P)^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 3689 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1484 _refine_ls_R_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.1996 _refine_ls_wR_factor_gt 0.1817 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.67299(11) 1.22213(6) 0.78086(11) 0.0324(4) Uani 1 1 d . . . O1 O 0.9287(5) 0.8905(3) 0.9572(5) 0.0300(16) Uani 1 1 d . . . O2 O 0.7895(6) 0.7952(3) 0.8337(6) 0.0341(16) Uani 1 1 d . . . S1 S 0.6545(2) 1.10238(12) 0.9083(2) 0.0288(6) Uani 1 1 d . . . S2 S 0.4988(2) 0.80626(12) 0.7567(2) 0.0308(6) Uani 1 1 d . . . S3 S 0.8218(2) 1.20054(13) 0.4330(2) 0.0322(6) Uani 1 1 d . . . N1 N 0.7308(7) 1.2035(4) 0.6391(8) 0.039(2) Uani 1 1 d . . . C1 C 0.8996(8) 0.9192(5) 1.0618(8) 0.027(2) Uani 1 1 d . . . C2 C 0.9448(8) 0.8779(5) 1.1730(8) 0.032(2) Uani 1 1 d . . . H2A H 0.9885 0.8242 1.1764 0.039 Uiso 1 1 calc R . . C3 C 0.9278(9) 0.9128(5) 1.2790(9) 0.036(3) Uani 1 1 d . . . H3A H 0.9581 0.8839 1.3549 0.043 Uiso 1 1 calc R . . C4 C 0.8639(8) 0.9930(5) 1.2701(9) 0.036(3) Uani 1 1 d . . . H4A H 0.8508 1.0188 1.3414 0.043 Uiso 1 1 calc R . . C5 C 0.8208(8) 1.0337(5) 1.1616(9) 0.034(2) Uani 1 1 d . . . H5A H 0.7784 1.0879 1.1593 0.041 Uiso 1 1 calc R . . C6 C 0.8358(8) 0.9994(5) 1.0524(8) 0.029(2) Uani 1 1 d . . . C7 C 0.7953(8) 1.0474(5) 0.9331(8) 0.032(2) Uani 1 1 d . . . H7A H 0.7907 1.0039 0.8667 0.038 Uiso 1 1 calc R . . H7B H 0.8549 1.0927 0.9282 0.038 Uiso 1 1 calc R . . C8 C 0.5539(8) 1.0114(5) 0.8492(8) 0.032(2) Uani 1 1 d . . . H8A H 0.5794 0.9580 0.9006 0.038 Uiso 1 1 calc R . . H8B H 0.4748 1.0281 0.8558 0.038 Uiso 1 1 calc R . . C9 C 0.5453(9) 0.9865(5) 0.7170(8) 0.032(2) Uani 1 1 d . . . H9A H 0.6233 0.9668 0.7103 0.038 Uiso 1 1 calc R . . H9B H 0.5225 1.0401 0.6652 0.038 Uiso 1 1 calc R . . C10 C 0.4543(8) 0.9111(5) 0.6700(8) 0.035(2) Uani 1 1 d . . . H10A H 0.4473 0.9002 0.5828 0.042 Uiso 1 1 calc R . . H10B H 0.3764 0.9302 0.6781 0.042 Uiso 1 1 calc R . . C11 C 0.5815(8) 0.7507(5) 0.6632(9) 0.034(2) Uani 1 1 d . . . H11A H 0.6196 0.6969 0.7070 0.041 Uiso 1 1 calc R . . H11B H 0.5256 0.7303 0.5871 0.041 Uiso 1 1 calc R . . C12 C 0.6736(8) 0.8069(5) 0.6313(8) 0.029(2) Uani 1 1 d . . . C13 C 0.6540(8) 0.8405(5) 0.5152(9) 0.034(2) Uani 1 1 d . . . H13A H 0.5840 0.8247 0.4557 0.041 Uiso 1 1 calc R . . C14 C 0.7348(10) 0.8972(6) 0.4832(10) 0.043(3) Uani 1 1 d . . . H14A H 0.7197 0.9208 0.4034 0.052 Uiso 1 1 calc R . . C15 C 0.8372(9) 0.9182(6) 0.5700(9) 0.039(3) Uani 1 1 d . . . H15A H 0.8930 0.9558 0.5481 0.046 Uiso 1 1 calc R . . C16 C 0.8611(9) 0.8864(5) 0.6878(9) 0.036(2) Uani 1 1 d . . . H16A H 0.9319 0.9020 0.7462 0.043 Uiso 1 1 calc R . . C17 C 0.7774(9) 0.8300(5) 0.7191(8) 0.031(2) Uani 1 1 d . . . C18 C 0.8999(9) 0.8009(5) 0.9170(9) 0.038(3) Uani 1 1 d . . . H18A H 0.9602 0.7780 0.8787 0.045 Uiso 1 1 calc R . . H18B H 0.9010 0.7627 0.9880 0.045 Uiso 1 1 calc R . . C19 C 0.7687(8) 1.2032(5) 0.5505(9) 0.031(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0452(8) 0.0102(5) 0.0394(7) 0.0024(5) 0.0067(6) 0.0055(5) O1 0.037(4) 0.007(2) 0.041(4) 0.000(3) 0.001(3) -0.001(3) O2 0.039(4) 0.017(3) 0.037(4) 0.005(3) -0.005(4) -0.004(3) S1 0.0375(16) 0.0049(8) 0.0394(15) 0.0004(9) 0.0023(12) 0.0005(9) S2 0.0410(16) 0.0071(9) 0.0393(15) -0.0001(9) 0.0021(13) -0.0035(10) S3 0.0390(16) 0.0151(10) 0.0398(15) -0.0017(10) 0.0055(13) 0.0019(10) N1 0.047(6) 0.014(4) 0.050(6) 0.003(4) 0.003(5) 0.004(4) C1 0.039(6) 0.009(4) 0.030(5) 0.003(4) 0.004(5) 0.005(4) C2 0.032(6) 0.013(4) 0.049(7) 0.011(4) 0.005(5) 0.007(4) C3 0.055(7) 0.008(4) 0.042(6) 0.008(4) 0.008(6) 0.001(4) C4 0.047(7) 0.012(4) 0.046(7) 0.000(4) 0.009(6) 0.000(4) C5 0.046(7) 0.009(4) 0.047(6) 0.003(4) 0.011(6) 0.001(4) C6 0.034(6) 0.013(4) 0.036(6) 0.009(4) 0.003(5) 0.001(4) C7 0.032(6) 0.012(4) 0.048(6) 0.004(4) 0.004(5) 0.003(4) C8 0.041(7) 0.018(4) 0.033(6) 0.003(4) 0.005(5) 0.001(4) C9 0.047(7) 0.005(3) 0.042(6) 0.002(4) 0.011(5) 0.002(4) C10 0.036(7) 0.011(4) 0.048(7) -0.005(4) -0.005(5) -0.011(4) C11 0.045(7) 0.016(4) 0.038(6) 0.001(4) 0.003(5) -0.004(4) C12 0.040(7) 0.009(4) 0.034(6) -0.002(4) 0.005(5) -0.003(4) C13 0.033(6) 0.021(4) 0.044(7) -0.005(4) 0.000(5) -0.002(4) C14 0.058(8) 0.030(5) 0.045(7) 0.000(5) 0.019(6) -0.007(5) C15 0.048(8) 0.022(5) 0.046(7) 0.002(5) 0.014(6) -0.009(5) C16 0.031(6) 0.020(4) 0.054(7) 0.002(5) 0.006(5) -0.001(4) C17 0.047(7) 0.011(4) 0.035(6) -0.003(4) 0.012(6) -0.002(4) C18 0.055(8) 0.006(4) 0.045(7) -0.007(4) 0.002(6) -0.001(4) C19 0.032(6) 0.008(4) 0.046(6) -0.003(4) -0.002(5) 0.004(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 Cu1 N1 1.936(8) . ? Cu1 S2 2.329(3) 2_656 ? Cu1 S1 2.356(3) . ? Cu1 S3 2.414(3) 4_586 ? O1 C1 1.395(9) . ? O1 C18 1.430(9) . ? O2 C17 1.380(10) . ? O2 C18 1.399(11) . ? S1 C7 1.809(9) . ? S1 C8 1.816(9) . ? S2 C11 1.827(9) . ? S2 C10 1.856(8) . ? S2 Cu1 2.329(3) 2_646 ? S3 C19 1.626(10) . ? S3 Cu1 2.414(3) 4_585 ? N1 C19 1.210(10) . ? C1 C2 1.386(11) . ? C1 C6 1.407(11) . ? C2 C3 1.381(12) . ? C3 C4 1.407(11) . ? C4 C5 1.353(12) . ? C5 C6 1.403(12) . ? C6 C7 1.502(12) . ? C8 C9 1.531(11) . ? C9 C10 1.554(11) . ? C11 C12 1.496(11) . ? C12 C13 1.379(12) . ? C12 C17 1.404(13) . ? C13 C14 1.397(12) . ? C14 C15 1.381(13) . ? C15 C16 1.384(12) . ? C16 C17 1.417(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 N1 Cu1 S2 114.0(2) . 2_656 ? N1 Cu1 S1 121.2(2) . . ? S2 Cu1 S1 107.82(10) 2_656 . ? N1 Cu1 S3 108.6(3) . 4_586 ? S2 Cu1 S3 107.79(11) 2_656 4_586 ? S1 Cu1 S3 95.15(11) . 4_586 ? C1 O1 C18 118.2(6) . . ? C17 O2 C18 117.7(7) . . ? C7 S1 C8 101.5(4) . . ? C7 S1 Cu1 102.2(3) . . ? C8 S1 Cu1 120.0(3) . . ? C11 S2 C10 101.2(4) . . ? C11 S2 Cu1 102.8(3) . 2_646 ? C10 S2 Cu1 104.5(3) . 2_646 ? C19 S3 Cu1 102.4(3) . 4_585 ? C19 N1 Cu1 171.9(6) . . ? C2 C1 O1 121.6(7) . . ? C2 C1 C6 121.3(8) . . ? O1 C1 C6 116.5(7) . . ? C3 C2 C1 121.6(8) . . ? C2 C3 C4 117.4(9) . . ? C5 C4 C3 121.0(9) . . ? C4 C5 C6 122.8(8) . . ? C5 C6 C1 115.9(8) . . ? C5 C6 C7 123.1(7) . . ? C1 C6 C7 120.9(8) . . ? C6 C7 S1 114.7(6) . . ? C9 C8 S1 114.5(6) . . ? C8 C9 C10 112.1(7) . . ? C9 C10 S2 111.0(6) . . ? C12 C11 S2 114.9(6) . . ? C13 C12 C17 119.2(8) . . ? C13 C12 C11 119.5(9) . . ? C17 C12 C11 121.2(8) . . ? C12 C13 C14 121.4(10) . . ? C15 C14 C13 118.7(10) . . ? C14 C15 C16 122.2(9) . . ? C15 C16 C17 118.3(10) . . ? O2 C17 C12 115.8(8) . . ? O2 C17 C16 124.1(9) . . ? C12 C17 C16 120.2(9) . . ? O2 C18 O1 112.0(7) . . ? N1 C19 S3 178.5(8) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.140 _refine_diff_density_min -1.754 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 950549' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Br2 Hg O2 S2' _chemical_formula_sum 'C18 H20 Br2 Hg O2 S2' _chemical_formula_weight 692.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9194(5) _cell_length_b 19.5010(6) _cell_length_c 8.3487(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.550(2) _cell_angle_gamma 90.00 _cell_volume 2099.35(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3225 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 27.15 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 11.346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2205 _exptl_absorpt_correction_T_max 0.4601 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18061 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5040 _reflns_number_gt 3921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0287P)^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 5040 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 Hg1 Hg 0.157774(17) 0.229449(10) 0.75589(2) 0.03150(8) Uani 1 1 d . . . Br1 Br 0.01909(4) 0.23945(3) 1.03850(6) 0.02869(13) Uani 1 1 d . . . Br2 Br 0.29402(5) 0.29781(3) 0.91457(7) 0.03961(15) Uani 1 1 d . . . S1 S 0.53020(11) -0.03064(7) 0.70006(15) 0.0304(3) Uani 1 1 d . . . S2 S 0.19300(10) 0.10091(6) 0.76448(13) 0.0224(3) Uani 1 1 d . . . O1 O 0.2383(3) -0.1140(2) 0.6435(4) 0.0353(9) Uani 1 1 d . . . O2 O 0.1082(3) -0.05814(18) 0.7544(4) 0.0320(9) Uani 1 1 d . . . C1 C 0.2945(4) -0.1428(2) 0.7722(6) 0.0269(12) Uani 1 1 d . . . C2 C 0.2497(5) -0.1734(3) 0.9033(6) 0.0332(13) Uani 1 1 d . . . H2A H 0.1766 -0.1736 0.9100 0.040 Uiso 1 1 calc R . . C3 C 0.3141(6) -0.2036(3) 1.0239(7) 0.0447(16) Uani 1 1 d . . . H3A H 0.2844 -0.2240 1.1136 0.054 Uiso 1 1 calc R . . C4 C 0.4193(5) -0.2043(3) 1.0147(7) 0.0428(15) Uani 1 1 d . . . H4A H 0.4624 -0.2262 1.0956 0.051 Uiso 1 1 calc R . . C5 C 0.4619(5) -0.1729(3) 0.8869(6) 0.0329(13) Uani 1 1 d . . . H5A H 0.5352 -0.1735 0.8815 0.039 Uiso 1 1 calc R . . C6 C 0.4025(4) -0.1405(3) 0.7660(6) 0.0269(12) Uani 1 1 d . . . C7 C 0.4539(4) -0.1039(3) 0.6331(6) 0.0322(12) Uani 1 1 d . . . H7A H 0.3997 -0.0885 0.5520 0.039 Uiso 1 1 calc R . . H7B H 0.4993 -0.1367 0.5803 0.039 Uiso 1 1 calc R . . C8 C 0.4324(5) 0.0358(3) 0.7186(6) 0.0403(15) Uani 1 1 d . . . H8A H 0.4662 0.0810 0.7086 0.048 Uiso 1 1 calc R . . H8B H 0.3801 0.0312 0.6274 0.048 Uiso 1 1 calc R . . C9 C 0.3766(5) 0.0354(3) 0.8719(6) 0.0341(13) Uani 1 1 d . . . H9A H 0.4280 0.0308 0.9643 0.041 Uiso 1 1 calc R . . H9B H 0.3297 -0.0047 0.8721 0.041 Uiso 1 1 calc R . . C10 C 0.3136(4) 0.1009(3) 0.8909(6) 0.0304(12) Uani 1 1 d . . . H10A H 0.3560 0.1410 0.8628 0.036 Uiso 1 1 calc R . . H10B H 0.2971 0.1058 1.0046 0.036 Uiso 1 1 calc R . . C11 C 0.1036(4) 0.0652(2) 0.9047(5) 0.0241(11) Uani 1 1 d . . . H11A H 0.1389 0.0284 0.9687 0.029 Uiso 1 1 calc R . . H11B H 0.0833 0.1015 0.9795 0.029 Uiso 1 1 calc R . . C12 C 0.0085(4) 0.0367(2) 0.8168(5) 0.0217(11) Uani 1 1 d . . . C13 C -0.0858(4) 0.0711(3) 0.8132(6) 0.0287(12) Uani 1 1 d . . . H13A H -0.0900 0.1146 0.8638 0.034 Uiso 1 1 calc R . . C14 C -0.1750(4) 0.0421(3) 0.7351(6) 0.0332(13) Uani 1 1 d . . . H14A H -0.2393 0.0658 0.7338 0.040 Uiso 1 1 calc R . . C15 C -0.1691(4) -0.0208(3) 0.6605(6) 0.0287(12) Uani 1 1 d . . . H15A H -0.2294 -0.0402 0.6074 0.034 Uiso 1 1 calc R . . C16 C -0.0754(4) -0.0559(3) 0.6627(6) 0.0279(12) Uani 1 1 d . . . H16A H -0.0713 -0.0991 0.6108 0.033 Uiso 1 1 calc R . . C17 C 0.0123(4) -0.0274(3) 0.7412(5) 0.0249(11) Uani 1 1 d . . . C18 C 0.1312(4) -0.1111(3) 0.6463(6) 0.0299(12) Uani 1 1 d . . . H18B H 0.1037 -0.1555 0.6828 0.036 Uiso 1 1 calc R . . H18A H 0.0996 -0.1011 0.5378 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Hg1 0.03233(14) 0.02672(12) 0.03470(12) 0.00463(9) -0.00395(9) -0.00022(10) Br1 0.0278(3) 0.0343(3) 0.0241(2) -0.0037(2) 0.0030(2) -0.0046(2) Br2 0.0316(3) 0.0383(3) 0.0493(3) -0.0135(3) 0.0060(3) -0.0073(3) S1 0.0288(8) 0.0346(7) 0.0283(7) 0.0023(6) 0.0050(5) 0.0025(6) S2 0.0269(7) 0.0222(6) 0.0183(6) -0.0003(5) 0.0015(5) -0.0019(5) O1 0.024(2) 0.054(2) 0.0283(18) 0.0063(18) 0.0051(16) 0.0041(19) O2 0.031(2) 0.0270(19) 0.037(2) -0.0095(16) -0.0066(16) 0.0059(18) C1 0.036(3) 0.019(2) 0.026(3) -0.002(2) 0.005(2) 0.008(2) C2 0.032(3) 0.029(3) 0.039(3) 0.001(2) 0.010(2) -0.002(3) C3 0.062(5) 0.033(3) 0.040(3) 0.017(3) 0.013(3) 0.006(3) C4 0.045(4) 0.039(3) 0.044(3) 0.013(3) -0.004(3) 0.001(3) C5 0.029(3) 0.031(3) 0.038(3) 0.000(2) 0.001(2) 0.004(3) C6 0.031(3) 0.025(3) 0.025(3) -0.003(2) 0.003(2) 0.004(2) C7 0.028(3) 0.041(3) 0.028(3) -0.001(2) 0.006(2) -0.002(3) C8 0.047(4) 0.040(3) 0.034(3) 0.008(3) 0.005(3) 0.007(3) C9 0.038(4) 0.037(3) 0.027(3) 0.001(2) 0.001(2) 0.005(3) C10 0.036(3) 0.031(3) 0.024(3) -0.005(2) -0.002(2) 0.002(3) C11 0.036(3) 0.017(2) 0.019(2) 0.0013(18) 0.001(2) -0.001(2) C12 0.027(3) 0.022(2) 0.016(2) 0.0054(18) 0.0040(19) -0.007(2) C13 0.040(4) 0.023(3) 0.023(2) 0.000(2) 0.002(2) 0.004(2) C14 0.032(3) 0.037(3) 0.031(3) 0.006(2) -0.001(2) 0.007(3) C15 0.026(3) 0.034(3) 0.026(3) 0.000(2) -0.002(2) -0.003(2) C16 0.032(3) 0.026(3) 0.026(2) 0.001(2) -0.001(2) -0.004(2) C17 0.028(3) 0.025(3) 0.021(2) 0.005(2) 0.001(2) -0.002(2) C18 0.027(3) 0.034(3) 0.029(3) -0.006(2) 0.004(2) 0.002(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 Hg1 Br2 2.5183(6) . ? Hg1 Br1 2.5435(5) 4_565 ? Hg1 S2 2.5479(12) . ? Hg1 Br1 3.0559(6) . ? Br1 Hg1 2.5435(5) 4_566 ? S1 C7 1.804(5) . ? S1 C8 1.824(6) . ? S2 C10 1.827(5) . ? S2 C11 1.832(5) . ? O1 C1 1.379(6) . ? O1 C18 1.386(6) . ? O2 C17 1.374(6) . ? O2 C18 1.416(6) . ? C1 C6 1.401(8) . ? C1 C2 1.402(7) . ? C2 C3 1.396(8) . ? C3 C4 1.365(9) . ? C4 C5 1.375(8) . ? C5 C6 1.383(7) . ? C6 C7 1.507(7) . ? C8 C9 1.507(7) . ? C9 C10 1.529(7) . ? C11 C12 1.498(7) . ? C12 C13 1.389(7) . ? C12 C17 1.404(7) . ? C13 C14 1.408(7) . ? C14 C15 1.379(7) . ? C15 C16 1.391(7) . ? C16 C17 1.389(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 Br2 Hg1 Br1 133.45(2) . 4_565 ? Br2 Hg1 S2 112.84(3) . . ? Br1 Hg1 S2 111.80(3) 4_565 . ? Br2 Hg1 Br1 89.093(17) . . ? Br1 Hg1 Br1 96.601(18) 4_565 . ? S2 Hg1 Br1 98.82(3) . . ? Hg1 Br1 Hg1 98.359(18) 4_566 . ? C7 S1 C8 102.8(3) . . ? C10 S2 C11 100.4(2) . . ? C10 S2 Hg1 99.23(17) . . ? C11 S2 Hg1 105.87(16) . . ? C1 O1 C18 118.7(4) . . ? C17 O2 C18 119.4(4) . . ? O1 C1 C6 115.8(4) . . ? O1 C1 C2 124.0(5) . . ? C6 C1 C2 120.2(5) . . ? C3 C2 C1 119.1(6) . . ? C4 C3 C2 120.9(6) . . ? C3 C4 C5 119.2(5) . . ? C4 C5 C6 122.6(6) . . ? C5 C6 C1 117.9(5) . . ? C5 C6 C7 120.3(5) . . ? C1 C6 C7 121.9(5) . . ? C6 C7 S1 113.8(3) . . ? C9 C8 S1 116.0(4) . . ? C8 C9 C10 111.7(4) . . ? C9 C10 S2 112.4(4) . . ? C12 C11 S2 111.0(3) . . ? C13 C12 C17 118.4(5) . . ? C13 C12 C11 121.6(4) . . ? C17 C12 C11 120.0(5) . . ? C12 C13 C14 120.5(5) . . ? C15 C14 C13 120.0(5) . . ? C14 C15 C16 120.3(5) . . ? C17 C16 C15 119.6(5) . . ? O2 C17 C16 124.7(4) . . ? O2 C17 C12 114.1(4) . . ? C16 C17 C12 121.2(5) . . ? O1 C18 O2 106.8(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.721 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.161 _database_code_depnum_ccdc_archive 'CCDC 950550' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Hg2 I4 O2 S2' _chemical_formula_sum 'C18 H20 Hg2 I4 O2 S2' _chemical_formula_weight 1241.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9144(3) _cell_length_b 8.0371(2) _cell_length_c 25.7905(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.2430(10) _cell_angle_gamma 90.00 _cell_volume 2634.24(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5125 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 26.21 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 16.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1456 _exptl_absorpt_correction_T_max 0.1777 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24671 _diffrn_reflns_av_R_equivalents 0.0810 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6354 _reflns_number_gt 4978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1256P)^2^+30.1331P] 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 6354 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2137 _refine_ls_wR_factor_gt 0.1988 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Hg1 Hg 0.09103(5) 0.79086(9) 0.70396(2) 0.0354(2) Uani 1 1 d . . . Hg2 Hg 0.08539(5) 0.72509(9) 0.56227(2) 0.0336(2) Uani 1 1 d . . . I1 I -0.10956(8) 0.74530(12) 0.71547(5) 0.0328(3) Uani 1 1 d . . . I2 I 0.14953(8) 0.50346(11) 0.64626(4) 0.0320(3) Uani 1 1 d . . . I3 I 0.12859(8) 1.01712(11) 0.62661(4) 0.0319(3) Uani 1 1 d . . . I4 I -0.11417(8) 0.72905(13) 0.51233(4) 0.0339(3) Uani 1 1 d . . . S1 S 0.2217(3) 0.8048(5) 1.00104(14) 0.0262(7) Uani 1 1 d . . . S2 S 0.2246(3) 0.8179(4) 0.79005(13) 0.0243(7) Uani 1 1 d . . . O1 O 0.4460(10) 0.7536(15) 0.9570(5) 0.041(3) Uani 1 1 d . . . O2 O 0.4457(10) 0.7712(15) 0.8733(4) 0.039(3) Uani 1 1 d . . . C1 C 0.4862(13) 0.739(2) 1.0093(7) 0.032(3) Uani 1 1 d . . . C2 C 0.5871(12) 0.7816(18) 1.0328(6) 0.028(3) Uani 1 1 d . . . H2A H 0.6348 0.8274 1.0125 0.034 Uiso 1 1 calc R . . C3 C 0.6176(16) 0.7567(17) 1.0860(7) 0.035(4) Uani 1 1 d . . . H3A H 0.6875 0.7840 1.1021 0.041 Uiso 1 1 calc R . . C4 C 0.5507(15) 0.694(2) 1.1164(7) 0.041(4) Uani 1 1 d . . . H4A H 0.5738 0.6800 1.1532 0.049 Uiso 1 1 calc R . . C5 C 0.4489(14) 0.6511(19) 1.0935(6) 0.035(4) Uani 1 1 d . . . H5A H 0.4017 0.6089 1.1147 0.042 Uiso 1 1 calc R . . C6 C 0.4164(13) 0.6699(19) 1.0397(7) 0.035(3) Uani 1 1 d . . . C7 C 0.3038(11) 0.6225(18) 1.0129(5) 0.027(3) Uani 1 1 d . . . H7A H 0.2733 0.5443 1.0358 0.032 Uiso 1 1 calc R . . H7B H 0.3061 0.5658 0.9791 0.032 Uiso 1 1 calc R . . C8 C 0.1396(12) 0.7598(18) 0.9367(5) 0.025(3) Uani 1 1 d . . . H8A H 0.1216 0.6400 0.9341 0.030 Uiso 1 1 calc R . . H8B H 0.0734 0.8246 0.9325 0.030 Uiso 1 1 calc R . . C9 C 0.2024(13) 0.808(2) 0.8936(5) 0.031(3) Uani 1 1 d . . . H9A H 0.2201 0.9280 0.8969 0.037 Uiso 1 1 calc R . . H9B H 0.2691 0.7447 0.8990 0.037 Uiso 1 1 calc R . . C10 C 0.1424(12) 0.7744(19) 0.8388(5) 0.027(3) Uani 1 1 d . . . H10A H 0.0787 0.8451 0.8320 0.032 Uiso 1 1 calc R . . H10B H 0.1197 0.6566 0.8360 0.032 Uiso 1 1 calc R . . C11 C 0.3016(10) 0.6258(19) 0.7956(6) 0.030(3) Uani 1 1 d . . . H11A H 0.3007 0.5747 0.8305 0.036 Uiso 1 1 calc R . . H11B H 0.2684 0.5465 0.7683 0.036 Uiso 1 1 calc R . . C12 C 0.4144(11) 0.6547(17) 0.7894(6) 0.027(3) Uani 1 1 d . . . C13 C 0.4509(13) 0.6067(19) 0.7448(6) 0.035(3) Uani 1 1 d . . . H13A H 0.4015 0.5665 0.7157 0.042 Uiso 1 1 calc R . . C14 C 0.5555(13) 0.6137(19) 0.7400(6) 0.034(3) Uani 1 1 d . . . H14A H 0.5779 0.5786 0.7085 0.041 Uiso 1 1 calc R . . C15 C 0.6260(13) 0.673(2) 0.7818(6) 0.035(4) Uani 1 1 d . . . H15A H 0.6988 0.6730 0.7799 0.042 Uiso 1 1 calc R . . C16 C 0.5933(14) 0.7335(19) 0.8275(7) 0.032(3) Uani 1 1 d . . . H16A H 0.6429 0.7812 0.8552 0.039 Uiso 1 1 calc R . . C17 C 0.4898(12) 0.7230(17) 0.8317(6) 0.025(3) Uani 1 1 d . . . C18 C 0.5113(12) 0.797(2) 0.9222(6) 0.035(4) Uani 1 1 d . . . H18B H 0.5741 0.7238 0.9263 0.042 Uiso 1 1 calc R . . H18A H 0.5341 0.9141 0.9267 0.042 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 Hg1 0.0273(3) 0.0616(5) 0.0191(3) 0.0017(2) 0.0091(2) 0.0024(3) Hg2 0.0251(3) 0.0596(4) 0.0177(3) -0.0026(2) 0.0081(2) -0.0033(2) I1 0.0260(5) 0.0349(5) 0.0416(6) -0.0035(4) 0.0172(5) -0.0009(4) I2 0.0416(6) 0.0239(5) 0.0319(5) 0.0009(4) 0.0101(4) 0.0090(4) I3 0.0415(6) 0.0250(5) 0.0306(5) -0.0003(4) 0.0106(4) -0.0065(4) I4 0.0248(5) 0.0407(6) 0.0349(6) 0.0022(4) 0.0018(4) 0.0003(4) S1 0.0277(18) 0.0324(18) 0.0207(16) 0.0016(13) 0.0105(14) 0.0028(14) S2 0.0272(17) 0.0286(17) 0.0188(15) 0.0000(13) 0.0087(13) -0.0003(14) O1 0.026(6) 0.073(9) 0.025(6) -0.002(5) 0.010(5) -0.009(5) O2 0.024(6) 0.081(9) 0.014(5) -0.008(5) 0.008(4) 0.004(5) C1 0.020(7) 0.048(9) 0.028(8) -0.004(6) 0.010(6) 0.003(6) C2 0.022(7) 0.043(8) 0.022(7) 0.002(6) 0.009(6) -0.001(6) C3 0.045(10) 0.023(7) 0.031(8) -0.006(6) -0.005(8) 0.001(6) C4 0.046(10) 0.047(10) 0.028(8) -0.003(7) 0.003(8) 0.009(8) C5 0.051(10) 0.030(8) 0.027(7) 0.015(6) 0.018(7) 0.011(7) C6 0.037(9) 0.029(8) 0.043(9) -0.002(7) 0.015(7) 0.010(7) C7 0.029(7) 0.030(7) 0.023(6) -0.005(5) 0.011(6) 0.000(6) C8 0.026(8) 0.046(8) 0.004(5) -0.003(5) 0.007(5) -0.006(6) C9 0.035(8) 0.053(9) 0.008(6) -0.003(6) 0.013(6) -0.010(7) C10 0.016(7) 0.052(9) 0.015(6) -0.005(6) 0.011(5) -0.003(6) C11 0.016(6) 0.040(8) 0.032(7) 0.000(6) 0.003(6) 0.004(6) C12 0.031(7) 0.020(7) 0.028(7) 0.002(5) -0.003(6) 0.004(5) C13 0.045(9) 0.028(8) 0.034(8) -0.002(6) 0.011(7) -0.006(7) C14 0.045(9) 0.036(8) 0.028(7) 0.009(6) 0.025(7) 0.012(7) C15 0.035(8) 0.044(9) 0.031(8) 0.008(7) 0.018(7) 0.008(7) C16 0.029(8) 0.043(9) 0.025(8) -0.001(6) 0.005(7) -0.005(6) C17 0.025(7) 0.028(7) 0.023(7) 0.003(5) 0.002(6) 0.004(5) C18 0.022(7) 0.067(11) 0.020(7) -0.009(7) 0.012(6) -0.011(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 Hg1 S2 2.567(4) . ? Hg1 I1 2.6844(12) . ? Hg1 I3 2.8047(11) . ? Hg1 I2 2.9190(11) . ? Hg2 S1 2.576(4) 4_575 ? Hg2 I4 2.6685(12) . ? Hg2 I2 2.8131(11) . ? Hg2 I3 2.8713(11) . ? S1 C7 1.802(15) . ? S1 C8 1.839(14) . ? S1 Hg2 2.576(4) 4_576 ? S2 C10 1.818(14) . ? S2 C11 1.829(15) . ? O1 C1 1.36(2) . ? O1 C18 1.381(18) . ? O2 C17 1.358(18) . ? O2 C18 1.404(19) . ? C1 C2 1.38(2) . ? C1 C6 1.41(2) . ? C2 C3 1.37(2) . ? C3 C4 1.36(3) . ? C4 C5 1.39(3) . ? C5 C6 1.39(2) . ? C6 C7 1.54(2) . ? C8 C9 1.538(18) . ? C9 C10 1.510(19) . ? C11 C12 1.51(2) . ? C12 C13 1.37(2) . ? C12 C17 1.43(2) . ? C13 C14 1.38(2) . ? C14 C15 1.37(2) . ? C15 C16 1.41(2) . ? C16 C17 1.36(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Hg1 I1 115.40(8) . . ? S2 Hg1 I3 112.69(8) . . ? I1 Hg1 I3 117.35(4) . . ? S2 Hg1 I2 108.24(8) . . ? I1 Hg1 I2 106.90(4) . . ? I3 Hg1 I2 93.28(3) . . ? S1 Hg2 I4 114.31(9) 4_575 . ? S1 Hg2 I2 105.86(9) 4_575 . ? I4 Hg2 I2 120.40(4) . . ? S1 Hg2 I3 110.28(9) 4_575 . ? I4 Hg2 I3 109.93(4) . . ? I2 Hg2 I3 94.14(3) . . ? Hg2 I2 Hg1 79.87(3) . . ? Hg1 I3 Hg2 80.83(3) . . ? C7 S1 C8 102.8(7) . . ? C7 S1 Hg2 105.4(5) . 4_576 ? C8 S1 Hg2 100.8(5) . 4_576 ? C10 S2 C11 99.2(7) . . ? C10 S2 Hg1 101.4(5) . . ? C11 S2 Hg1 105.6(5) . . ? C1 O1 C18 119.8(13) . . ? C17 O2 C18 118.7(12) . . ? O1 C1 C2 125.3(15) . . ? O1 C1 C6 114.5(14) . . ? C2 C1 C6 120.2(15) . . ? C3 C2 C1 118.9(15) . . ? C4 C3 C2 122.1(17) . . ? C3 C4 C5 119.9(15) . . ? C4 C5 C6 119.7(15) . . ? C5 C6 C1 119.3(16) . . ? C5 C6 C7 121.0(14) . . ? C1 C6 C7 119.7(14) . . ? C6 C7 S1 110.8(10) . . ? C9 C8 S1 108.0(10) . . ? C10 C9 C8 112.5(12) . . ? C9 C10 S2 110.3(10) . . ? C12 C11 S2 112.5(10) . . ? C13 C12 C17 117.1(14) . . ? C13 C12 C11 121.7(14) . . ? C17 C12 C11 121.0(13) . . ? C12 C13 C14 123.4(15) . . ? C15 C14 C13 117.9(14) . . ? C14 C15 C16 121.7(15) . . ? C17 C16 C15 119.2(16) . . ? O2 C17 C16 126.9(15) . . ? O2 C17 C12 112.7(13) . . ? C16 C17 C12 120.5(14) . . ? O1 C18 O2 101.9(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 13.931 _refine_diff_density_min -3.081 _refine_diff_density_rms 0.524 _database_code_depnum_ccdc_archive 'CCDC 950551' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O8 Pd S2' _chemical_formula_sum 'C18 H20 N2 O8 Pd S2' _chemical_formula_weight 562.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8401(2) _cell_length_b 9.9305(2) _cell_length_c 12.6660(3) _cell_angle_alpha 80.6080(10) _cell_angle_beta 73.4820(10) _cell_angle_gamma 80.9150(10) _cell_volume 1044.39(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7626 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.35 _exptl_crystal_description Plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 1.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7798 _exptl_absorpt_correction_T_max 0.9667 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17103 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4100 _reflns_number_gt 3806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0295P)^2^+0.9735P] 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 4100 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.12586(2) 0.429673(16) 0.176088(13) 0.01790(6) Uani 1 1 d . . . O1 O 0.3040(2) 0.28080(17) 0.34983(13) 0.0270(4) Uani 1 1 d . . . O2 O 0.1081(2) 0.17156(18) 0.48711(14) 0.0289(4) Uani 1 1 d . . . O3 O 0.2296(2) 0.59587(16) 0.19168(14) 0.0269(4) Uani 1 1 d . . . O4 O 0.2268(3) 0.81625(19) 0.16324(19) 0.0513(6) Uani 1 1 d . . . O5 O 0.0979(3) 0.7179(2) 0.0826(2) 0.0707(8) Uani 1 1 d . . . O6 O -0.0790(2) 0.51090(18) 0.28152(15) 0.0314(4) Uani 1 1 d . . . O7 O -0.1857(3) 0.5423(2) 0.1414(2) 0.0564(6) Uani 1 1 d . . . O8 O -0.3112(3) 0.6248(3) 0.2955(3) 0.0778(9) Uani 1 1 d . . . S1 S 0.36669(7) 0.38019(5) 0.05983(4) 0.01926(12) Uani 1 1 d . . . S2 S 0.00645(7) 0.24535(6) 0.17177(4) 0.01985(12) Uani 1 1 d . . . N1 N 0.1812(3) 0.7144(2) 0.14474(18) 0.0314(5) Uani 1 1 d . . . N2 N -0.1957(3) 0.5610(2) 0.2372(2) 0.0412(6) Uani 1 1 d . . . C1 C 0.4153(3) 0.1748(2) 0.31047(19) 0.0222(5) Uani 1 1 d . . . C2 C 0.4252(3) 0.0412(3) 0.3654(2) 0.0281(5) Uani 1 1 d . . . H2A H 0.3500 0.0178 0.4338 0.034 Uiso 1 1 calc R . . C3 C 0.5450(3) -0.0569(3) 0.3199(2) 0.0314(6) Uani 1 1 d . . . H3A H 0.5507 -0.1480 0.3571 0.038 Uiso 1 1 calc R . . C4 C 0.6569(3) -0.0245(3) 0.2208(2) 0.0283(5) Uani 1 1 d . . . H4A H 0.7409 -0.0916 0.1914 0.034 Uiso 1 1 calc R . . C5 C 0.6442(3) 0.1082(2) 0.16516(19) 0.0239(5) Uani 1 1 d . . . H5A H 0.7200 0.1308 0.0969 0.029 Uiso 1 1 calc R . . C6 C 0.5235(3) 0.2077(2) 0.20720(18) 0.0199(5) Uani 1 1 d . . . C7 C 0.5102(3) 0.3485(2) 0.14449(19) 0.0228(5) Uani 1 1 d . . . H7A H 0.6163 0.3651 0.0951 0.027 Uiso 1 1 calc R . . H7B H 0.4799 0.4164 0.1983 0.027 Uiso 1 1 calc R . . C8 C 0.3960(3) 0.2242(2) -0.00313(18) 0.0227(5) Uani 1 1 d . . . H8A H 0.3679 0.2480 -0.0748 0.027 Uiso 1 1 calc R . . H8B H 0.5106 0.1899 -0.0200 0.027 Uiso 1 1 calc R . . C9 C 0.3041(3) 0.1073(2) 0.06312(18) 0.0210(5) Uani 1 1 d . . . H9A H 0.3190 0.0912 0.1389 0.025 Uiso 1 1 calc R . . H9B H 0.3485 0.0225 0.0280 0.025 Uiso 1 1 calc R . . C10 C 0.1273(3) 0.1346(2) 0.07131(19) 0.0230(5) Uani 1 1 d . . . H10A H 0.0842 0.0450 0.0889 0.028 Uiso 1 1 calc R . . H10B H 0.1143 0.1755 -0.0028 0.028 Uiso 1 1 calc R . . C11 C 0.0012(3) 0.1305(2) 0.30174(19) 0.0245(5) Uani 1 1 d . . . H11A H -0.0420 0.0451 0.2999 0.029 Uiso 1 1 calc R . . H11B H 0.1100 0.1056 0.3111 0.029 Uiso 1 1 calc R . . C12 C -0.1026(3) 0.2036(2) 0.39688(18) 0.0224(5) Uani 1 1 d . . . C13 C -0.2605(3) 0.2530(3) 0.4007(2) 0.0280(5) Uani 1 1 d . . . H13A H -0.3043 0.2348 0.3448 0.034 Uiso 1 1 calc R . . C14 C -0.3549(3) 0.3276(3) 0.4835(2) 0.0316(6) Uani 1 1 d . . . H14A H -0.4619 0.3608 0.4839 0.038 Uiso 1 1 calc R . . C15 C -0.2928(3) 0.3538(3) 0.5660(2) 0.0364(6) Uani 1 1 d . . . H15A H -0.3570 0.4054 0.6230 0.044 Uiso 1 1 calc R . . C16 C -0.1375(3) 0.3046(3) 0.5652(2) 0.0337(6) Uani 1 1 d . . . H16A H -0.0947 0.3223 0.6217 0.040 Uiso 1 1 calc R . . C17 C -0.0441(3) 0.2295(3) 0.48175(19) 0.0254(5) Uani 1 1 d . . . C18 C 0.2221(3) 0.2638(3) 0.4644(2) 0.0306(6) Uani 1 1 d . . . H18A H 0.2995 0.2291 0.5085 0.037 Uiso 1 1 calc R . . H18B H 0.1689 0.3541 0.4869 0.037 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 0.01904(10) 0.01521(10) 0.02005(10) -0.00212(6) -0.00690(7) -0.00072(7) O1 0.0237(9) 0.0295(9) 0.0249(8) 0.0002(7) -0.0047(7) -0.0018(7) O2 0.0222(9) 0.0370(10) 0.0268(9) -0.0004(7) -0.0074(7) -0.0031(8) O3 0.0333(10) 0.0159(8) 0.0337(9) -0.0029(7) -0.0130(8) -0.0018(7) O4 0.0584(14) 0.0196(10) 0.0674(15) -0.0030(9) -0.0001(11) -0.0130(10) O5 0.088(2) 0.0511(14) 0.0861(18) 0.0320(13) -0.0605(17) -0.0186(14) O6 0.0276(10) 0.0269(9) 0.0351(10) -0.0083(7) -0.0016(8) 0.0025(8) O7 0.0469(14) 0.0470(13) 0.0862(18) -0.0120(12) -0.0426(13) 0.0123(11) O8 0.0414(15) 0.0510(15) 0.108(2) -0.0071(14) 0.0141(14) 0.0243(12) S1 0.0200(3) 0.0156(3) 0.0208(3) 0.0025(2) -0.0057(2) -0.0025(2) S2 0.0181(3) 0.0209(3) 0.0221(3) -0.0041(2) -0.0070(2) -0.0024(2) N1 0.0302(12) 0.0260(11) 0.0311(11) 0.0039(9) -0.0007(9) -0.0045(9) N2 0.0235(13) 0.0239(12) 0.0678(18) -0.0036(11) -0.0038(12) 0.0041(10) C1 0.0179(12) 0.0274(12) 0.0242(11) 0.0006(9) -0.0112(9) -0.0047(10) C2 0.0272(14) 0.0317(13) 0.0242(12) 0.0073(10) -0.0095(10) -0.0062(11) C3 0.0356(15) 0.0255(13) 0.0343(14) 0.0061(10) -0.0174(11) -0.0018(11) C4 0.0283(14) 0.0262(13) 0.0317(13) -0.0035(10) -0.0142(11) 0.0040(10) C5 0.0223(12) 0.0283(12) 0.0223(11) -0.0017(9) -0.0074(9) -0.0053(10) C6 0.0185(11) 0.0218(11) 0.0223(11) 0.0021(9) -0.0111(9) -0.0048(9) C7 0.0189(12) 0.0231(12) 0.0279(12) 0.0020(9) -0.0100(9) -0.0053(9) C8 0.0240(12) 0.0212(11) 0.0209(11) -0.0031(9) -0.0046(9) 0.0012(10) C9 0.0236(12) 0.0174(11) 0.0221(11) -0.0045(9) -0.0071(9) 0.0010(9) C10 0.0248(13) 0.0227(12) 0.0250(12) -0.0088(9) -0.0098(10) -0.0015(10) C11 0.0276(13) 0.0219(11) 0.0246(12) -0.0010(9) -0.0071(10) -0.0061(10) C12 0.0216(12) 0.0223(12) 0.0225(11) -0.0003(9) -0.0033(9) -0.0071(10) C13 0.0243(13) 0.0336(13) 0.0281(12) 0.0004(10) -0.0078(10) -0.0119(11) C14 0.0204(13) 0.0353(14) 0.0351(14) -0.0001(11) -0.0027(11) -0.0052(11) C15 0.0301(15) 0.0435(16) 0.0303(14) -0.0109(12) 0.0039(11) -0.0049(12) C16 0.0298(15) 0.0482(16) 0.0232(12) -0.0072(11) -0.0039(10) -0.0077(12) C17 0.0219(13) 0.0293(13) 0.0236(12) 0.0007(10) -0.0045(9) -0.0058(10) C18 0.0253(13) 0.0435(15) 0.0255(12) -0.0062(11) -0.0084(10) -0.0065(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 O6 2.0565(17) . ? Pd1 O3 2.0713(16) . ? Pd1 S1 2.2506(6) . ? Pd1 S2 2.2679(6) . ? O1 C1 1.375(3) . ? O1 C18 1.421(3) . ? O2 C17 1.393(3) . ? O2 C18 1.407(3) . ? O3 N1 1.296(3) . ? O4 N1 1.225(3) . ? O5 N1 1.215(3) . ? O6 N2 1.304(3) . ? O7 N2 1.234(3) . ? O8 N2 1.228(3) . ? S1 C8 1.806(2) . ? S1 C7 1.842(2) . ? S2 C10 1.812(2) . ? S2 C11 1.836(2) . ? C1 C2 1.395(3) . ? C1 C6 1.407(3) . ? C2 C3 1.384(4) . ? C3 C4 1.385(4) . ? C4 C5 1.393(3) . ? C5 C6 1.384(3) . ? C6 C7 1.496(3) . ? C8 C9 1.518(3) . ? C9 C10 1.520(3) . ? C11 C12 1.506(3) . ? C12 C17 1.392(3) . ? C12 C13 1.395(3) . ? C13 C14 1.381(4) . ? C14 C15 1.387(4) . ? C15 C16 1.380(4) . ? C16 C17 1.386(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 O6 Pd1 O3 87.15(7) . . ? O6 Pd1 S1 168.87(5) . . ? O3 Pd1 S1 81.90(5) . . ? O6 Pd1 S2 90.33(5) . . ? O3 Pd1 S2 176.11(5) . . ? S1 Pd1 S2 100.70(2) . . ? C1 O1 C18 117.14(19) . . ? C17 O2 C18 116.0(2) . . ? N1 O3 Pd1 116.37(15) . . ? N2 O6 Pd1 116.06(16) . . ? C8 S1 C7 103.92(11) . . ? C8 S1 Pd1 116.15(8) . . ? C7 S1 Pd1 106.53(8) . . ? C10 S2 C11 100.68(11) . . ? C10 S2 Pd1 112.69(8) . . ? C11 S2 Pd1 107.83(8) . . ? O5 N1 O4 123.9(2) . . ? O5 N1 O3 118.4(2) . . ? O4 N1 O3 117.6(2) . . ? O8 N2 O7 123.7(3) . . ? O8 N2 O6 116.7(3) . . ? O7 N2 O6 119.6(2) . . ? O1 C1 C2 124.4(2) . . ? O1 C1 C6 115.64(19) . . ? C2 C1 C6 119.9(2) . . ? C3 C2 C1 119.8(2) . . ? C2 C3 C4 121.0(2) . . ? C3 C4 C5 118.9(2) . . ? C6 C5 C4 121.4(2) . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C7 120.4(2) . . ? C1 C6 C7 120.7(2) . . ? C6 C7 S1 115.66(15) . . ? C9 C8 S1 117.24(16) . . ? C8 C9 C10 113.36(19) . . ? C9 C10 S2 117.22(16) . . ? C12 C11 S2 108.65(16) . . ? C17 C12 C13 117.4(2) . . ? C17 C12 C11 121.8(2) . . ? C13 C12 C11 120.8(2) . . ? C14 C13 C12 121.7(2) . . ? C13 C14 C15 119.7(3) . . ? C16 C15 C14 119.9(3) . . ? C15 C16 C17 119.9(2) . . ? C16 C17 C12 121.5(2) . . ? C16 C17 O2 119.0(2) . . ? C12 C17 O2 119.4(2) . . ? O2 C18 O1 111.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.533 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 950552' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H40 N2 O10 Pd S4' _chemical_formula_sum 'C36 H40 N2 O10 Pd S4' _chemical_formula_weight 895.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1618(3) _cell_length_b 12.8043(3) _cell_length_c 19.3631(4) _cell_angle_alpha 71.4600(10) _cell_angle_beta 74.7480(10) _cell_angle_gamma 88.068(2) _cell_volume 2754.00(11) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5041 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.09 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8702 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46812 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0790 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.00 _reflns_number_total 13250 _reflns_number_gt 9298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0364P)^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 13250 _refine_ls_number_parameters 718 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.78755(2) 0.822078(19) 0.865195(13) 0.01756(7) Uani 1 1 d . . . Pd2 Pd 0.5000 0.5000 0.5000 0.01874(9) Uani 1 2 d S . . S1 S 0.79705(7) 0.97399(7) 0.75688(4) 0.01945(18) Uani 1 1 d . . . S2 S 0.68672(7) 0.90170(7) 0.95494(4) 0.02110(18) Uani 1 1 d . . . S3 S 0.88919(7) 0.74118(7) 0.77756(4) 0.02205(19) Uani 1 1 d . . . S4 S 0.78182(7) 0.67238(7) 0.97310(4) 0.02057(18) Uani 1 1 d . . . S5 S 0.63331(7) 0.45092(7) 0.57095(4) 0.02185(19) Uani 1 1 d . . . S6 S 0.34721(7) 0.49945(7) 0.60423(4) 0.02245(19) Uani 1 1 d . . . O1 O 1.12818(18) 1.01000(18) 0.79585(12) 0.0232(5) Uani 1 1 d . . . O2 O 1.00017(19) 0.9094(2) 0.90244(12) 0.0301(6) Uani 1 1 d . . . O3 O 0.5490(2) 0.68100(19) 0.79064(13) 0.0348(6) Uani 1 1 d . . . O4 O 0.5527(2) 0.7369(2) 0.89076(12) 0.0359(6) Uani 1 1 d . . . O5 O 0.57961(19) 0.73355(18) 0.47119(12) 0.0299(6) Uani 1 1 d . . . O6 O 0.4332(2) 0.84381(18) 0.48872(12) 0.0284(6) Uani 1 1 d . . . O7 O 0.5525(2) 0.9898(2) 0.26177(14) 0.0463(7) Uani 1 1 d . . . O8 O 0.6192(2) 1.0102(2) 0.14301(13) 0.0390(7) Uani 1 1 d . . . O9 O 0.5852(3) 0.8473(2) 0.22617(18) 0.0630(9) Uani 1 1 d . . . O10 O 0.1664(3) 0.6874(3) 0.2584(2) 0.1139(17) Uani 1 1 d . . . O11 O 0.0711(4) 0.5666(3) 0.24161(18) 0.0833(13) Uani 1 1 d . . . O12 O 0.1442(4) 0.5211(3) 0.3313(2) 0.0947(15) Uani 1 1 d . . . O13 O 0.7550(3) 0.4928(3) 0.14755(17) 0.0774(12) Uani 1 1 d . . . O14 O 0.7947(2) 0.3570(2) 0.10500(14) 0.0412(7) Uani 1 1 d . . . O15 O 0.7225(3) 0.3280(3) 0.22433(14) 0.0621(9) Uani 1 1 d . . . N1 N 0.5868(2) 0.9488(3) 0.20999(18) 0.0321(7) Uani 1 1 d . . . N2 N 0.1296(3) 0.5928(3) 0.2768(2) 0.0420(9) Uani 1 1 d . . . N3 N 0.7566(2) 0.3923(3) 0.16003(16) 0.0303(7) Uani 1 1 d . . . C1 C 1.1245(3) 0.9758(3) 0.73486(17) 0.0202(7) Uani 1 1 d . . . C2 C 1.2193(3) 0.9277(3) 0.70234(18) 0.0288(8) Uani 1 1 d . . . H2A H 1.2818 0.9119 0.7242 0.035 Uiso 1 1 calc R . . C3 C 1.2213(3) 0.9029(3) 0.6375(2) 0.0338(9) Uani 1 1 d . . . H3A H 1.2855 0.8697 0.6146 0.041 Uiso 1 1 calc R . . C4 C 1.1297(3) 0.9265(3) 0.60560(18) 0.0295(8) Uani 1 1 d . . . H4A H 1.1314 0.9098 0.5609 0.035 Uiso 1 1 calc R . . C5 C 1.0363(3) 0.9743(3) 0.63917(17) 0.0239(8) Uani 1 1 d . . . H5A H 0.9742 0.9907 0.6170 0.029 Uiso 1 1 calc R . . C6 C 1.0315(3) 0.9988(2) 0.70504(16) 0.0181(7) Uani 1 1 d . . . C7 C 0.9296(3) 1.0509(3) 0.74270(17) 0.0206(7) Uani 1 1 d . . . H7A H 0.9269 1.1281 0.7108 0.025 Uiso 1 1 calc R . . H7B H 0.9374 1.0518 0.7921 0.025 Uiso 1 1 calc R . . C8 C 0.6927(3) 1.0747(3) 0.77161(18) 0.0257(8) Uani 1 1 d . . . H8A H 0.7139 1.1424 0.7273 0.031 Uiso 1 1 calc R . . H8B H 0.6179 1.0454 0.7724 0.031 Uiso 1 1 calc R . . C9 C 0.6769(3) 1.1077(3) 0.84218(17) 0.0260(8) Uani 1 1 d . . . H9A H 0.6354 1.1765 0.8359 0.031 Uiso 1 1 calc R . . H9B H 0.7530 1.1237 0.8472 0.031 Uiso 1 1 calc R . . C10 C 0.6120(3) 1.0205(3) 0.91477(18) 0.0279(8) Uani 1 1 d . . . H10A H 0.5441 0.9935 0.9051 0.033 Uiso 1 1 calc R . . H10B H 0.5840 1.0573 0.9535 0.033 Uiso 1 1 calc R . . C11 C 0.7942(3) 0.9669(3) 0.98136(18) 0.0254(8) Uani 1 1 d . . . H11A H 0.8438 1.0201 0.9354 0.030 Uiso 1 1 calc R . . H11B H 0.7555 1.0084 1.0154 0.030 Uiso 1 1 calc R . . C12 C 0.8667(3) 0.8834(3) 1.02033(17) 0.0218(7) Uani 1 1 d . . . C13 C 0.8311(3) 0.8298(3) 1.09805(18) 0.0310(9) Uani 1 1 d . . . H13A H 0.7584 0.8431 1.1262 0.037 Uiso 1 1 calc R . . C14 C 0.9002(3) 0.7577(3) 1.13467(19) 0.0333(9) Uani 1 1 d . . . H14A H 0.8750 0.7216 1.1877 0.040 Uiso 1 1 calc R . . C15 C 1.0053(3) 0.7382(3) 1.09439(19) 0.0304(9) Uani 1 1 d . . . H15A H 1.0535 0.6904 1.1202 0.036 Uiso 1 1 calc R . . C16 C 1.0425(3) 0.7872(3) 1.01661(18) 0.0273(8) Uani 1 1 d . . . H16A H 1.1144 0.7715 0.9890 0.033 Uiso 1 1 calc R . . C17 C 0.9726(3) 0.8597(3) 0.97984(18) 0.0242(8) Uani 1 1 d . . . C18 C 1.1198(3) 0.9257(3) 0.86443(17) 0.0237(8) Uani 1 1 d . . . H18A H 1.1629 0.9477 0.8949 0.028 Uiso 1 1 calc R . . H18B H 1.1504 0.8572 0.8553 0.028 Uiso 1 1 calc R . . C19 C 0.6148(3) 0.7425(3) 0.71978(18) 0.0267(8) Uani 1 1 d . . . C20 C 0.5629(3) 0.8095(3) 0.6671(2) 0.0363(9) Uani 1 1 d . . . H20A H 0.4829 0.8176 0.6804 0.044 Uiso 1 1 calc R . . C21 C 0.6287(4) 0.8643(3) 0.5950(2) 0.0423(11) Uani 1 1 d . . . H21A H 0.5938 0.9109 0.5587 0.051 Uiso 1 1 calc R . . C22 C 0.7447(4) 0.8519(3) 0.5755(2) 0.0408(10) Uani 1 1 d . . . H22A H 0.7896 0.8896 0.5258 0.049 Uiso 1 1 calc R . . C23 C 0.7958(3) 0.7842(3) 0.62859(18) 0.0328(9) Uani 1 1 d . . . H23A H 0.8756 0.7751 0.6147 0.039 Uiso 1 1 calc R . . C24 C 0.7317(3) 0.7297(3) 0.70182(17) 0.0220(7) Uani 1 1 d . . . C25 C 0.7887(3) 0.6579(3) 0.75900(18) 0.0244(8) Uani 1 1 d . . . H25A H 0.8297 0.6005 0.7397 0.029 Uiso 1 1 calc R . . H25B H 0.7303 0.6206 0.8066 0.029 Uiso 1 1 calc R . . C26 C 0.9822(3) 0.6396(3) 0.81607(18) 0.0293(8) Uani 1 1 d . . . H26A H 1.0166 0.6034 0.7778 0.035 Uiso 1 1 calc R . . H26B H 1.0451 0.6790 0.8229 0.035 Uiso 1 1 calc R . . C27 C 0.9306(3) 0.5494(3) 0.89048(18) 0.0282(8) Uani 1 1 d . . . H27A H 0.8597 0.5177 0.8873 0.034 Uiso 1 1 calc R . . H27B H 0.9847 0.4899 0.8976 0.034 Uiso 1 1 calc R . . C28 C 0.9029(3) 0.5882(3) 0.95897(18) 0.0267(8) Uani 1 1 d . . . H28A H 0.9712 0.6303 0.9568 0.032 Uiso 1 1 calc R . . H28B H 0.8908 0.5220 1.0044 0.032 Uiso 1 1 calc R . . C29 C 0.6644(3) 0.5788(3) 0.98266(17) 0.0219(7) Uani 1 1 d . . . H29A H 0.6673 0.5723 0.9326 0.026 Uiso 1 1 calc R . . H29B H 0.6730 0.5045 1.0167 0.026 Uiso 1 1 calc R . . C30 C 0.5509(3) 0.6200(3) 1.01395(17) 0.0200(7) Uani 1 1 d . . . C31 C 0.4975(3) 0.5818(3) 1.09075(18) 0.0260(8) Uani 1 1 d . . . H31A H 0.5352 0.5321 1.1239 0.031 Uiso 1 1 calc R . . C32 C 0.3905(3) 0.6145(3) 1.12009(19) 0.0331(9) Uani 1 1 d . . . H32A H 0.3548 0.5866 1.1728 0.040 Uiso 1 1 calc R . . C33 C 0.3364(3) 0.6878(3) 1.0725(2) 0.0343(9) Uani 1 1 d . . . H33A H 0.2629 0.7101 1.0925 0.041 Uiso 1 1 calc R . . C34 C 0.3880(3) 0.7295(3) 0.9953(2) 0.0302(8) Uani 1 1 d . . . H34A H 0.3507 0.7806 0.9626 0.036 Uiso 1 1 calc R . . C35 C 0.4954(3) 0.6951(3) 0.96683(18) 0.0245(8) Uani 1 1 d . . . C36 C 0.4891(3) 0.7407(3) 0.83734(18) 0.0328(9) Uani 1 1 d . . . H36A H 0.4112 0.7069 0.8639 0.039 Uiso 1 1 calc R . . H36B H 0.4831 0.8180 0.8068 0.039 Uiso 1 1 calc R . . C37 C 0.3312(3) 0.7960(3) 0.48966(18) 0.0264(8) Uani 1 1 d . . . C38 C 0.2783(3) 0.8477(3) 0.43322(19) 0.0352(9) Uani 1 1 d . . . H38A H 0.3156 0.9088 0.3913 0.042 Uiso 1 1 calc R . . C39 C 0.1706(4) 0.8089(3) 0.4390(2) 0.0424(11) Uani 1 1 d . . . H39A H 0.1344 0.8424 0.4000 0.051 Uiso 1 1 calc R . . C40 C 0.1146(3) 0.7211(3) 0.5012(2) 0.0395(10) Uani 1 1 d . . . H40A H 0.0392 0.6971 0.5060 0.047 Uiso 1 1 calc R . . C41 C 0.1697(3) 0.6691(3) 0.5562(2) 0.0314(9) Uani 1 1 d . . . H41A H 0.1320 0.6087 0.5984 0.038 Uiso 1 1 calc R . . C42 C 0.2799(3) 0.7046(3) 0.55027(17) 0.0224(8) Uani 1 1 d . . . C43 C 0.3413(3) 0.6407(3) 0.60797(17) 0.0232(8) Uani 1 1 d . . . H43A H 0.2993 0.6413 0.6591 0.028 Uiso 1 1 calc R . . H43B H 0.4192 0.6739 0.5956 0.028 Uiso 1 1 calc R . . C44 C 0.3644(3) 0.4220(3) 0.69714(17) 0.0271(8) Uani 1 1 d . . . H44A H 0.3044 0.4434 0.7351 0.033 Uiso 1 1 calc R . . H44B H 0.3489 0.3429 0.7055 0.033 Uiso 1 1 calc R . . C45 C 0.4773(3) 0.4334(3) 0.71358(17) 0.0281(8) Uani 1 1 d . . . H45A H 0.4682 0.3988 0.7685 0.034 Uiso 1 1 calc R . . H45B H 0.4980 0.5127 0.7005 0.034 Uiso 1 1 calc R . . C46 C 0.5748(3) 0.3811(3) 0.67083(17) 0.0283(8) Uani 1 1 d . . . H46A H 0.5479 0.3057 0.6772 0.034 Uiso 1 1 calc R . . H46B H 0.6378 0.3736 0.6954 0.034 Uiso 1 1 calc R . . C47 C 0.6821(3) 0.5845(3) 0.57118(17) 0.0238(8) Uani 1 1 d . . . H47A H 0.6161 0.6259 0.5884 0.029 Uiso 1 1 calc R . . H47B H 0.7320 0.5739 0.6056 0.029 Uiso 1 1 calc R . . C48 C 0.7470(3) 0.6463(3) 0.49157(18) 0.0224(7) Uani 1 1 d . . . C49 C 0.8599(3) 0.6253(3) 0.4650(2) 0.0313(9) Uani 1 1 d . . . H49A H 0.8971 0.5754 0.4984 0.038 Uiso 1 1 calc R . . C50 C 0.9191(3) 0.6761(3) 0.3904(2) 0.0383(10) Uani 1 1 d . . . H50A H 0.9968 0.6616 0.3729 0.046 Uiso 1 1 calc R . . C51 C 0.8654(3) 0.7475(3) 0.3418(2) 0.0366(9) Uani 1 1 d . . . H51A H 0.9060 0.7814 0.2904 0.044 Uiso 1 1 calc R . . C52 C 0.7521(3) 0.7709(3) 0.36690(19) 0.0318(9) Uani 1 1 d . . . H52A H 0.7155 0.8209 0.3332 0.038 Uiso 1 1 calc R . . C53 C 0.6934(3) 0.7203(3) 0.44176(18) 0.0231(7) Uani 1 1 d . . . C54 C 0.5321(3) 0.8326(3) 0.43540(19) 0.0316(9) Uani 1 1 d . . . H54A H 0.5868 0.8965 0.4203 0.038 Uiso 1 1 calc R . . H54B H 0.5132 0.8279 0.3898 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 0.01809(14) 0.01652(14) 0.01832(13) -0.00627(10) -0.00424(10) -0.00057(10) Pd2 0.0226(2) 0.01875(19) 0.01650(17) -0.00538(15) -0.00817(15) 0.00070(15) S1 0.0179(4) 0.0199(4) 0.0200(4) -0.0056(3) -0.0052(3) 0.0005(3) S2 0.0189(4) 0.0230(5) 0.0215(4) -0.0092(4) -0.0027(4) -0.0010(4) S3 0.0223(5) 0.0208(4) 0.0231(4) -0.0084(4) -0.0045(4) 0.0017(4) S4 0.0221(5) 0.0194(4) 0.0207(4) -0.0057(3) -0.0072(4) -0.0005(4) S5 0.0262(5) 0.0211(4) 0.0201(4) -0.0063(4) -0.0097(4) 0.0020(4) S6 0.0262(5) 0.0218(5) 0.0191(4) -0.0056(4) -0.0067(4) 0.0005(4) O1 0.0242(13) 0.0243(13) 0.0231(12) -0.0103(10) -0.0060(10) -0.0005(10) O2 0.0182(13) 0.0501(16) 0.0198(12) -0.0064(11) -0.0070(10) -0.0015(12) O3 0.0327(15) 0.0272(14) 0.0349(14) -0.0031(12) -0.0015(12) 0.0009(12) O4 0.0237(14) 0.0503(17) 0.0239(13) 0.0056(12) -0.0102(11) -0.0089(12) O5 0.0250(14) 0.0254(14) 0.0285(13) 0.0035(11) -0.0042(11) 0.0006(11) O6 0.0328(15) 0.0247(14) 0.0273(13) -0.0084(11) -0.0067(12) -0.0017(12) O7 0.0534(19) 0.0496(19) 0.0374(15) -0.0135(14) -0.0143(14) -0.0026(15) O8 0.0323(16) 0.0446(17) 0.0310(14) -0.0015(13) -0.0070(12) 0.0063(13) O9 0.052(2) 0.0266(17) 0.086(2) -0.0077(16) 0.0107(18) 0.0010(15) O10 0.091(3) 0.064(3) 0.151(4) -0.057(3) 0.060(3) -0.038(2) O11 0.141(4) 0.073(2) 0.083(2) -0.048(2) -0.086(3) 0.053(2) O12 0.156(4) 0.089(3) 0.090(3) -0.057(2) -0.093(3) 0.083(3) O13 0.126(3) 0.042(2) 0.056(2) -0.0184(17) -0.009(2) 0.024(2) O14 0.0447(17) 0.0444(17) 0.0354(15) -0.0189(14) -0.0043(13) -0.0020(14) O15 0.083(3) 0.063(2) 0.0261(15) 0.0005(15) -0.0057(16) -0.0147(19) N1 0.0165(16) 0.0305(19) 0.045(2) -0.0054(17) -0.0083(15) -0.0002(14) N2 0.043(2) 0.035(2) 0.047(2) -0.0209(19) -0.0026(19) 0.0122(18) N3 0.0226(17) 0.040(2) 0.0283(17) -0.0077(16) -0.0108(14) 0.0002(15) C1 0.0206(18) 0.0168(17) 0.0213(16) -0.0063(14) -0.0015(14) -0.0044(14) C2 0.0225(19) 0.036(2) 0.0310(19) -0.0159(17) -0.0069(16) 0.0051(17) C3 0.028(2) 0.036(2) 0.040(2) -0.0223(19) 0.0006(18) 0.0052(18) C4 0.036(2) 0.030(2) 0.0214(17) -0.0118(16) 0.0001(16) -0.0030(17) C5 0.027(2) 0.0212(18) 0.0208(17) -0.0038(15) -0.0057(15) 0.0016(15) C6 0.0181(17) 0.0146(16) 0.0169(15) -0.0022(13) 0.0005(14) -0.0043(13) C7 0.0188(18) 0.0180(17) 0.0240(17) -0.0063(14) -0.0042(15) -0.0025(14) C8 0.0203(18) 0.0264(19) 0.0306(18) -0.0084(16) -0.0088(16) 0.0079(15) C9 0.025(2) 0.0226(19) 0.0312(18) -0.0103(16) -0.0087(16) 0.0094(16) C10 0.0192(18) 0.032(2) 0.0314(19) -0.0129(17) -0.0027(16) 0.0059(16) C11 0.0231(19) 0.029(2) 0.0290(18) -0.0158(16) -0.0071(16) 0.0008(16) C12 0.0239(19) 0.0206(18) 0.0243(17) -0.0124(15) -0.0053(15) -0.0046(15) C13 0.036(2) 0.034(2) 0.0247(18) -0.0140(17) -0.0043(17) -0.0021(18) C14 0.044(2) 0.034(2) 0.0202(17) -0.0058(16) -0.0079(18) -0.0033(19) C15 0.034(2) 0.028(2) 0.034(2) -0.0073(17) -0.0214(18) -0.0012(17) C16 0.0224(19) 0.034(2) 0.0296(19) -0.0141(17) -0.0088(16) 0.0004(16) C17 0.0265(19) 0.0266(19) 0.0223(17) -0.0091(15) -0.0084(15) -0.0056(16) C18 0.0174(18) 0.031(2) 0.0252(17) -0.0104(16) -0.0072(15) 0.0014(15) C19 0.035(2) 0.0190(18) 0.0275(18) -0.0087(15) -0.0086(17) -0.0009(16) C20 0.043(2) 0.032(2) 0.041(2) -0.0126(19) -0.021(2) 0.0092(19) C21 0.073(3) 0.030(2) 0.034(2) -0.0115(19) -0.030(2) 0.013(2) C22 0.071(3) 0.029(2) 0.0197(18) -0.0057(17) -0.010(2) -0.008(2) C23 0.043(2) 0.031(2) 0.0273(19) -0.0143(17) -0.0071(18) -0.0022(18) C24 0.034(2) 0.0158(17) 0.0186(16) -0.0061(14) -0.0103(16) -0.0013(15) C25 0.029(2) 0.0196(18) 0.0274(18) -0.0104(15) -0.0083(16) 0.0004(15) C26 0.025(2) 0.030(2) 0.036(2) -0.0138(17) -0.0101(17) 0.0089(17) C27 0.024(2) 0.029(2) 0.0347(19) -0.0104(17) -0.0144(17) 0.0073(16) C28 0.0217(19) 0.0269(19) 0.0304(18) -0.0042(16) -0.0114(16) 0.0038(16) C29 0.0233(18) 0.0175(17) 0.0236(17) -0.0053(14) -0.0055(15) -0.0029(15) C30 0.0188(17) 0.0197(17) 0.0222(16) -0.0088(14) -0.0031(14) -0.0055(14) C31 0.029(2) 0.0251(19) 0.0226(17) -0.0074(15) -0.0051(16) -0.0066(16) C32 0.029(2) 0.044(2) 0.0242(18) -0.0161(18) 0.0048(17) -0.0107(18) C33 0.022(2) 0.042(2) 0.046(2) -0.027(2) -0.0040(18) -0.0010(18) C34 0.023(2) 0.029(2) 0.042(2) -0.0146(18) -0.0097(18) 0.0009(16) C35 0.0202(18) 0.0251(19) 0.0270(18) -0.0068(16) -0.0052(15) -0.0070(15) C36 0.025(2) 0.044(2) 0.0271(19) -0.0052(18) -0.0119(17) 0.0057(18) C37 0.031(2) 0.028(2) 0.0275(18) -0.0158(16) -0.0125(17) 0.0094(17) C38 0.052(3) 0.030(2) 0.0279(19) -0.0097(17) -0.018(2) 0.013(2) C39 0.053(3) 0.046(3) 0.043(2) -0.021(2) -0.031(2) 0.022(2) C40 0.029(2) 0.054(3) 0.053(3) -0.033(2) -0.021(2) 0.014(2) C41 0.031(2) 0.032(2) 0.036(2) -0.0154(18) -0.0106(18) 0.0071(18) C42 0.0243(19) 0.0240(19) 0.0237(17) -0.0146(15) -0.0068(15) 0.0091(16) C43 0.0275(19) 0.0198(18) 0.0250(17) -0.0090(15) -0.0098(16) 0.0034(15) C44 0.036(2) 0.0241(19) 0.0175(16) -0.0025(15) -0.0053(16) -0.0018(16) C45 0.035(2) 0.030(2) 0.0165(16) -0.0027(15) -0.0066(16) -0.0067(17) C46 0.038(2) 0.025(2) 0.0204(17) -0.0001(15) -0.0139(16) 0.0004(17) C47 0.0248(19) 0.0273(19) 0.0208(17) -0.0076(15) -0.0085(15) -0.0020(16) C48 0.0233(19) 0.0202(18) 0.0240(17) -0.0085(15) -0.0044(15) -0.0041(15) C49 0.028(2) 0.032(2) 0.040(2) -0.0199(18) -0.0084(18) -0.0016(17) C50 0.028(2) 0.042(2) 0.047(2) -0.027(2) 0.004(2) -0.0098(19) C51 0.037(2) 0.035(2) 0.033(2) -0.0150(19) 0.0055(19) -0.0192(19) C52 0.038(2) 0.028(2) 0.0247(18) -0.0032(16) -0.0039(17) -0.0169(18) C53 0.0209(19) 0.0193(18) 0.0281(18) -0.0100(15) -0.0005(15) -0.0089(15) C54 0.036(2) 0.025(2) 0.0275(19) -0.0020(16) -0.0068(18) 0.0004(17) _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 S3 2.3256(8) . ? Pd1 S4 2.3302(8) . ? Pd1 S2 2.3418(8) . ? Pd1 S1 2.3429(8) . ? Pd2 S5 2.3378(8) . ? Pd2 S5 2.3378(8) 2_666 ? Pd2 S6 2.3547(8) 2_666 ? Pd2 S6 2.3547(8) . ? S1 C8 1.813(3) . ? S1 C7 1.829(3) . ? S2 C10 1.809(3) . ? S2 C11 1.834(3) . ? S3 C26 1.804(3) . ? S3 C25 1.822(3) . ? S4 C28 1.809(3) . ? S4 C29 1.829(3) . ? S5 C46 1.807(3) . ? S5 C47 1.831(3) . ? S6 C44 1.820(3) . ? S6 C43 1.832(3) . ? O1 C1 1.395(4) . ? O1 C18 1.402(4) . ? O2 C17 1.381(4) . ? O2 C18 1.436(4) . ? O3 C19 1.386(4) . ? O3 C36 1.410(4) . ? O4 C35 1.388(4) . ? O4 C36 1.434(4) . ? O5 C53 1.378(4) . ? O5 C54 1.423(4) . ? O6 C37 1.395(4) . ? O6 C54 1.401(4) . ? O7 N1 1.247(4) . ? O8 N1 1.248(3) . ? O9 N1 1.236(4) . ? O10 N2 1.214(4) . ? O11 N2 1.224(5) . ? O12 N2 1.208(4) . ? O13 N3 1.231(4) . ? O14 N3 1.260(4) . ? O15 N3 1.225(3) . ? C1 C6 1.383(4) . ? C1 C2 1.386(4) . ? C2 C3 1.384(5) . ? C3 C4 1.390(5) . ? C4 C5 1.380(4) . ? C5 C6 1.394(4) . ? C6 C7 1.514(4) . ? C8 C9 1.519(4) . ? C9 C10 1.524(4) . ? C11 C12 1.504(4) . ? C12 C13 1.394(4) . ? C12 C17 1.400(4) . ? C13 C14 1.381(5) . ? C14 C15 1.372(5) . ? C15 C16 1.388(4) . ? C16 C17 1.391(4) . ? C19 C20 1.386(4) . ? C19 C24 1.390(5) . ? C20 C21 1.381(5) . ? C21 C22 1.379(6) . ? C22 C23 1.388(5) . ? C23 C24 1.390(4) . ? C24 C25 1.505(4) . ? C26 C27 1.522(4) . ? C27 C28 1.514(4) . ? C29 C30 1.505(4) . ? C30 C31 1.387(4) . ? C30 C35 1.391(4) . ? C31 C32 1.385(5) . ? C32 C33 1.375(5) . ? C33 C34 1.391(5) . ? C34 C35 1.393(4) . ? C37 C38 1.388(4) . ? C37 C42 1.388(5) . ? C38 C39 1.380(5) . ? C39 C40 1.392(5) . ? C40 C41 1.386(5) . ? C41 C42 1.393(5) . ? C42 C43 1.514(4) . ? C44 C45 1.511(5) . ? C45 C46 1.524(4) . ? C47 C48 1.501(4) . ? C48 C49 1.382(5) . ? C48 C53 1.401(4) . ? C49 C50 1.384(5) . ? C50 C51 1.374(5) . ? C51 C52 1.391(5) . ? C52 C53 1.386(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 S3 Pd1 S4 97.07(3) . . ? S3 Pd1 S2 179.04(3) . . ? S4 Pd1 S2 82.09(3) . . ? S3 Pd1 S1 82.92(3) . . ? S4 Pd1 S1 178.76(3) . . ? S2 Pd1 S1 97.91(3) . . ? S5 Pd2 S5 180.0 . 2_666 ? S5 Pd2 S6 85.69(3) . 2_666 ? S5 Pd2 S6 94.31(3) 2_666 2_666 ? S5 Pd2 S6 94.31(3) . . ? S5 Pd2 S6 85.69(3) 2_666 . ? S6 Pd2 S6 179.999(1) 2_666 . ? C8 S1 C7 101.07(15) . . ? C8 S1 Pd1 113.74(11) . . ? C7 S1 Pd1 104.36(10) . . ? C10 S2 C11 100.83(16) . . ? C10 S2 Pd1 112.83(11) . . ? C11 S2 Pd1 106.31(11) . . ? C26 S3 C25 102.29(16) . . ? C26 S3 Pd1 112.13(11) . . ? C25 S3 Pd1 108.21(11) . . ? C28 S4 C29 101.41(15) . . ? C28 S4 Pd1 111.77(11) . . ? C29 S4 Pd1 106.09(10) . . ? C46 S5 C47 101.32(15) . . ? C46 S5 Pd2 115.56(12) . . ? C47 S5 Pd2 102.65(10) . . ? C44 S6 C43 101.79(15) . . ? C44 S6 Pd2 116.37(11) . . ? C43 S6 Pd2 106.73(11) . . ? C1 O1 C18 115.8(2) . . ? C17 O2 C18 116.0(2) . . ? C19 O3 C36 116.6(3) . . ? C35 O4 C36 117.2(3) . . ? C53 O5 C54 117.8(3) . . ? C37 O6 C54 117.4(3) . . ? O9 N1 O7 118.8(3) . . ? O9 N1 O8 121.2(3) . . ? O7 N1 O8 119.9(3) . . ? O12 N2 O10 122.9(5) . . ? O12 N2 O11 116.5(4) . . ? O10 N2 O11 120.5(4) . . ? O15 N3 O13 121.0(3) . . ? O15 N3 O14 120.6(3) . . ? O13 N3 O14 118.4(3) . . ? C6 C1 C2 122.1(3) . . ? C6 C1 O1 119.4(3) . . ? C2 C1 O1 118.2(3) . . ? C3 C2 C1 118.9(3) . . ? C2 C3 C4 120.3(3) . . ? C5 C4 C3 119.7(3) . . ? C4 C5 C6 121.2(3) . . ? C1 C6 C5 117.8(3) . . ? C1 C6 C7 120.3(3) . . ? C5 C6 C7 121.9(3) . . ? C6 C7 S1 110.7(2) . . ? C9 C8 S1 117.7(2) . . ? C8 C9 C10 114.1(3) . . ? C9 C10 S2 118.1(2) . . ? C12 C11 S2 111.9(2) . . ? C13 C12 C17 118.4(3) . . ? C13 C12 C11 120.7(3) . . ? C17 C12 C11 120.9(3) . . ? C14 C13 C12 120.8(3) . . ? C15 C14 C13 119.9(3) . . ? C14 C15 C16 121.1(3) . . ? C15 C16 C17 118.9(3) . . ? O2 C17 C16 123.2(3) . . ? O2 C17 C12 116.0(3) . . ? C16 C17 C12 120.8(3) . . ? O1 C18 O2 105.4(2) . . ? C20 C19 O3 120.0(3) . . ? C20 C19 C24 121.4(3) . . ? O3 C19 C24 118.5(3) . . ? C21 C20 C19 119.3(4) . . ? C22 C21 C20 120.4(3) . . ? C21 C22 C23 119.8(4) . . ? C22 C23 C24 120.9(4) . . ? C23 C24 C19 118.1(3) . . ? C23 C24 C25 120.2(3) . . ? C19 C24 C25 121.7(3) . . ? C24 C25 S3 110.1(2) . . ? C27 C26 S3 117.9(2) . . ? C28 C27 C26 114.2(3) . . ? C27 C28 S4 118.7(2) . . ? C30 C29 S4 111.0(2) . . ? C31 C30 C35 118.2(3) . . ? C31 C30 C29 120.6(3) . . ? C35 C30 C29 121.2(3) . . ? C32 C31 C30 121.4(3) . . ? C33 C32 C31 119.6(3) . . ? C32 C33 C34 120.7(3) . . ? C33 C34 C35 118.8(3) . . ? O4 C35 C30 117.4(3) . . ? O4 C35 C34 121.3(3) . . ? C30 C35 C34 121.3(3) . . ? O3 C36 O4 106.7(3) . . ? C38 C37 C42 121.6(3) . . ? C38 C37 O6 118.7(3) . . ? C42 C37 O6 119.5(3) . . ? C39 C38 C37 118.9(4) . . ? C38 C39 C40 120.6(3) . . ? C41 C40 C39 119.5(4) . . ? C40 C41 C42 120.7(4) . . ? C37 C42 C41 118.4(3) . . ? C37 C42 C43 122.1(3) . . ? C41 C42 C43 119.5(3) . . ? C42 C43 S6 106.5(2) . . ? C45 C44 S6 118.7(2) . . ? C44 C45 C46 114.0(3) . . ? C45 C46 S5 117.8(2) . . ? C48 C47 S5 106.9(2) . . ? C49 C48 C53 118.9(3) . . ? C49 C48 C47 119.8(3) . . ? C53 C48 C47 121.1(3) . . ? C48 C49 C50 120.7(3) . . ? C51 C50 C49 119.9(4) . . ? C50 C51 C52 120.7(3) . . ? C53 C52 C51 119.2(3) . . ? O5 C53 C52 123.6(3) . . ? O5 C53 C48 115.8(3) . . ? C52 C53 C48 120.5(3) . . ? O6 C54 O5 106.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.662 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 950553'