# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Javier Ruiz' _publ_contact_author_email JRUIZ@UNIOVI.ES _publ_section_title ; Metal-induced tautomerization of oxazole and thiazole molecules to heterocyclic carbenes ; _publ_requested_category FM loop_ _publ_author_name 'Javier Ruiz' 'Bernabe F. Perandones' # Attachment '4b6b7b8b.cif.cif' data_4b _database_code_depnum_ccdc_archive 'CCDC 716673' _audit_creation_date 2008-04-15T16:55:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H11 Mn N3 O3 S, Cl O4, 0.5(C2 H5 Cl4)' _chemical_formula_sum 'C17 H13 Cl3 Mn N3 O7 S' _chemical_formula_weight 564.66 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 10.1874(5) _cell_length_b 12.8131(5) _cell_length_c 16.3439(7) _cell_angle_alpha 90 _cell_angle_beta 93.621(2) _cell_angle_gamma 90 _cell_volume 2129.15(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1966 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.14 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.872 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_number 33014 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4348 _reflns_number_gt 3647 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (BRUKER AXS, 2006)' _computing_cell_refinement 'APEX2 (BRUKER AXS, 2006)' _computing_data_reduction 'APEX2 (BRUKER AXS, 2006)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1504P)^2^+4.3839P] 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_number_reflns 4348 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2284 _refine_ls_wR_factor_gt 0.2194 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.109 _refine_diff_density_min -1.943 _refine_diff_density_rms 0.167 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Mn1 Mn 0.84746(6) 0.10639(5) 0.83912(4) 0.0246(2) Uani 1 1 d . . . S3 S 1.09049(11) 0.38236(9) 0.75936(7) 0.0326(3) Uani 1 1 d . . . C2 C 1.0186(4) 0.2633(4) 0.7580(3) 0.0283(9) Uani 1 1 d . . . H2 H 1.034 0.2122 0.7176 0.034 Uiso 1 1 calc R . . N1 N 0.9393(3) 0.2473(3) 0.8176(2) 0.0259(8) Uani 1 1 d . . . C5 C 0.9332(4) 0.3348(4) 0.8665(3) 0.0294(9) Uani 1 1 d . . . H5 H 0.8802 0.3383 0.9122 0.035 Uiso 1 1 calc R . . C4 C 1.0096(5) 0.4156(4) 0.8437(3) 0.0325(10) Uani 1 1 d . . . H4 H 1.0168 0.4811 0.8709 0.039 Uiso 1 1 calc R . . N6 N 0.6811(4) 0.1929(3) 0.8480(2) 0.0307(8) Uani 1 1 d . . . C7 C 0.6377(5) 0.2336(4) 0.9170(4) 0.0449(13) Uani 1 1 d . . . H7 H 0.684 0.2178 0.9678 0.054 Uiso 1 1 calc R . . C8 C 0.5288(6) 0.2972(5) 0.9172(5) 0.0605(17) Uani 1 1 d . . . H8 H 0.5013 0.3253 0.9672 0.073 Uiso 1 1 calc R . . C9 C 0.4604(6) 0.3196(5) 0.8443(5) 0.0567(17) Uani 1 1 d . . . H9 H 0.3856 0.364 0.8431 0.068 Uiso 1 1 calc R . . C10 C 0.5013(5) 0.2772(4) 0.7728(4) 0.0501(15) Uani 1 1 d . . . H10 H 0.4532 0.2898 0.722 0.06 Uiso 1 1 calc R . . C11 C 0.6132(5) 0.2159(3) 0.7759(3) 0.0342(11) Uani 1 1 d . . . N12 N 0.7775(4) 0.1113(3) 0.7195(2) 0.0299(8) Uani 1 1 d . . . C13 C 0.6683(5) 0.1689(3) 0.7033(3) 0.0334(10) Uani 1 1 d . . . C14 C 0.6136(6) 0.1807(4) 0.6230(3) 0.0441(14) Uani 1 1 d . . . H14 H 0.5369 0.2219 0.6124 0.053 Uiso 1 1 calc R . . C15 C 0.6715(7) 0.1324(5) 0.5601(3) 0.0515(17) Uani 1 1 d . . . H15 H 0.6355 0.1401 0.5054 0.062 Uiso 1 1 calc R . . C16 C 0.7820(6) 0.0724(5) 0.5763(3) 0.0472(14) Uani 1 1 d . . . H16 H 0.8227 0.0375 0.5333 0.057 Uiso 1 1 calc R . . C17 C 0.8327(5) 0.0641(4) 0.6565(3) 0.0367(11) Uani 1 1 d . . . H17 H 0.9098 0.0234 0.6677 0.044 Uiso 1 1 calc R . . C18 C 0.7648(5) -0.0176(4) 0.8533(3) 0.0336(10) Uani 1 1 d . . . O19 O 0.7162(4) -0.0970(3) 0.8592(3) 0.0468(9) Uani 1 1 d . . . C20 C 0.9018(5) 0.1115(3) 0.9472(3) 0.0304(10) Uani 1 1 d . . . O21 O 0.9385(4) 0.1134(3) 1.0146(2) 0.0407(9) Uani 1 1 d . . . C22 C 0.9965(5) 0.0354(3) 0.8219(3) 0.0293(9) Uani 1 1 d . . . O23 O 1.0904(3) -0.0108(3) 0.8121(2) 0.0369(8) Uani 1 1 d . . . Cl1A Cl 0.2585(7) 0.1286(13) 0.6207(7) 0.0199(12) Uani 0.47 1 d P A 1 O2AW O 0.3262(3) 0.1095(3) 0.5509(2) 0.0355(6) Uani 0.47 1 d P A 1 O3AW O 0.2397(8) 0.2461(8) 0.6222(6) 0.0355(6) Uani 0.47 1 d P A 1 O4AW O 0.3201(10) 0.1022(17) 0.6936(8) 0.0355(6) Uani 0.47 1 d P A 1 O5AW O 0.1174(9) 0.0880(7) 0.6121(5) 0.0355(6) Uani 0.47 1 d P A 1 Cl1B Cl 0.2297(14) 0.1404(13) 0.6130(11) 0.0199(12) Uani 0.31 1 d P B 2 O2BW O 0.3262(3) 0.1095(3) 0.5509(2) 0.0355(6) Uani 0.31 1 d P B 2 O3BW O 0.2055(12) 0.2385(13) 0.6172(9) 0.0355(6) Uani 0.31 1 d P B 2 O4BW O 0.290(3) 0.0935(19) 0.6933(12) 0.0355(6) Uani 0.31 1 d P B 2 O5BW O 0.1267(14) 0.0634(11) 0.5973(8) 0.0355(6) Uani 0.31 1 d P B 2 Cl1C Cl 0.2245(19) 0.1152(15) 0.6086(13) 0.018(2) Uani 0.22 1 d P C 3 O2CW O 0.3262(3) 0.1095(3) 0.5509(2) 0.0355(6) Uani 0.22 1 d P C 3 O3CW O 0.1459(16) 0.2074(13) 0.5973(9) 0.0355(6) Uani 0.22 1 d P C 3 O4CW O 0.294(4) 0.117(2) 0.6941(18) 0.0355(6) Uani 0.22 1 d P C 3 O5CW O 0.1545(17) 0.0187(14) 0.5984(10) 0.0355(6) Uani 0.22 1 d P C 3 C6AW C 0.3559(8) 0.0659(7) 0.9017(5) 0.075(2) Uani 0.5 1 d P D 1 H6A1 H 0.3351 0.0595 0.8419 0.09 Uiso 0.5 1 calc PR D 1 H6A2 H 0.4453 0.0959 0.9097 0.09 Uiso 0.5 1 calc PR D 1 Cl7A Cl 0.24371(19) 0.15410(16) 0.94158(12) 0.0698(5) Uani 0.5 1 d P D 1 Cl8A Cl 0.3580(3) -0.0512(3) 0.94160(19) 0.0563(7) Uani 0.5 1 d P D 1 C6BW C 0.3559(8) 0.0659(7) 0.9017(5) 0.075(2) Uani 0.5 1 d P E 2 H6B1 H 0.3066 0.0086 0.873 0.09 Uiso 0.5 1 calc PR E 2 H6B2 H 0.4075 0.1024 0.8611 0.09 Uiso 0.5 1 calc PR E 2 Cl7B Cl 0.24371(19) 0.15410(16) 0.94158(12) 0.0698(5) Uani 0.5 1 d P E 2 Cl8B Cl 0.4636(4) 0.0131(3) 0.9788(3) 0.0737(10) Uani 0.5 1 d P . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0274(4) 0.0287(4) 0.0176(4) 0.0005(2) -0.0010(3) 0.0094(2) S3 0.0284(6) 0.0385(7) 0.0308(6) -0.0009(4) 0.0006(5) 0.0016(4) C2 0.026(2) 0.036(2) 0.023(2) -0.0057(17) 0.0000(16) 0.0038(17) N1 0.0240(17) 0.0333(19) 0.0197(16) -0.0017(14) -0.0040(13) 0.0101(14) C5 0.031(2) 0.033(2) 0.024(2) -0.0024(17) -0.0029(17) 0.0082(18) C4 0.033(2) 0.032(2) 0.032(2) -0.0034(19) -0.0046(18) 0.0087(18) N6 0.0270(18) 0.0304(19) 0.034(2) 0.0021(15) -0.0042(15) 0.0065(15) C7 0.037(3) 0.050(3) 0.048(3) -0.002(2) 0.002(2) 0.021(2) C8 0.041(3) 0.060(4) 0.079(5) -0.023(3) 0.001(3) 0.023(3) C9 0.036(3) 0.040(3) 0.092(5) -0.012(3) -0.011(3) 0.019(2) C10 0.039(3) 0.025(2) 0.082(4) 0.000(3) -0.031(3) 0.004(2) C11 0.034(2) 0.021(2) 0.046(3) 0.0051(19) -0.014(2) -0.0016(17) N12 0.033(2) 0.032(2) 0.0249(19) 0.0013(14) -0.0037(15) -0.0047(15) C13 0.038(2) 0.026(2) 0.034(2) 0.0128(18) -0.014(2) -0.0111(18) C14 0.052(3) 0.034(3) 0.042(3) 0.018(2) -0.026(2) -0.024(2) C15 0.067(4) 0.056(3) 0.029(3) 0.018(2) -0.022(3) -0.043(3) C16 0.059(3) 0.060(3) 0.022(2) 0.000(2) 0.000(2) -0.036(3) C17 0.044(3) 0.043(3) 0.022(2) -0.0014(19) -0.0027(19) -0.013(2) C18 0.035(2) 0.038(3) 0.028(2) 0.0001(19) 0.0014(18) 0.016(2) O19 0.045(2) 0.039(2) 0.056(2) 0.0034(17) 0.0040(18) 0.0009(17) C20 0.034(2) 0.031(2) 0.026(2) 0.0019(17) 0.0064(18) 0.0177(18) O21 0.054(2) 0.049(2) 0.0185(17) -0.0020(13) -0.0039(15) 0.0233(16) C22 0.039(2) 0.029(2) 0.0200(19) -0.0009(16) -0.0016(17) 0.0054(19) O23 0.0374(18) 0.0423(19) 0.0316(17) -0.0013(14) 0.0054(14) 0.0155(15) Cl1A 0.004(3) 0.029(3) 0.026(2) 0.0015(18) -0.002(2) 0.000(3) O2AW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O3AW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O4AW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O5AW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) Cl1B 0.004(3) 0.029(3) 0.026(2) 0.0015(18) -0.002(2) 0.000(3) O2BW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O3BW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O4BW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O5BW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) Cl1C 0.010(5) 0.018(5) 0.026(5) 0.001(4) 0.007(4) -0.009(4) O2CW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O3CW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O4CW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) O5CW 0.0340(15) 0.0428(16) 0.0308(11) -0.0087(10) 0.0111(11) -0.0077(12) C6AW 0.076(5) 0.080(5) 0.066(5) -0.019(4) -0.002(4) 0.019(4) Cl7A 0.0656(10) 0.0787(12) 0.0652(11) -0.0176(9) 0.0055(8) 0.0108(9) Cl8A 0.0582(17) 0.0559(17) 0.0539(16) 0.0084(13) -0.0031(13) -0.0064(14) C6BW 0.076(5) 0.080(5) 0.066(5) -0.019(4) -0.002(4) 0.019(4) Cl7B 0.0656(10) 0.0787(12) 0.0652(11) -0.0176(9) 0.0055(8) 0.0108(9) Cl8B 0.058(2) 0.073(2) 0.090(3) 0.020(2) 0.0030(17) 0.0037(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Mn1 C22 1.807(5) . ? Mn1 C20 1.819(5) . ? Mn1 C18 1.819(5) . ? Mn1 N6 2.038(4) . ? Mn1 N12 2.039(4) . ? Mn1 N1 2.074(4) . ? S3 C2 1.691(5) . ? S3 C4 1.705(5) . ? C2 N1 1.321(6) . ? C2 H2 0.95 . ? N1 C5 1.380(6) . ? C5 C4 1.361(7) . ? C5 H5 0.95 . ? C4 H4 0.95 . ? N6 C7 1.342(7) . ? N6 C11 1.360(6) . ? C7 C8 1.377(7) . ? C7 H7 0.95 . ? C8 C9 1.373(10) . ? C8 H8 0.95 . ? C9 C10 1.377(9) . ? C9 H9 0.95 . ? C10 C11 1.383(7) . ? C10 H10 0.95 . ? C11 C13 1.474(7) . ? N12 C13 1.347(6) . ? N12 C17 1.348(6) . ? C13 C14 1.400(7) . ? C14 C15 1.366(10) . ? C14 H14 0.95 . ? C15 C16 1.375(10) . ? C15 H15 0.95 . ? C16 C17 1.382(7) . ? C16 H16 0.95 . ? C17 H17 0.95 . ? C18 O19 1.138(6) . ? C20 O21 1.140(6) . ? C22 O23 1.145(6) . ? Cl1A O4AW 1.354(17) . ? Cl1A O2AW 1.392(14) . ? Cl1A O3AW 1.518(19) . ? Cl1A O5AW 1.527(12) . ? Cl1B O3BW 1.28(2) . ? Cl1B O5BW 1.45(2) . ? Cl1B O4BW 1.54(3) . ? Cl1C O5CW 1.43(2) . ? Cl1C O3CW 1.43(3) . ? Cl1C O4CW 1.52(4) . ? C6AW Cl8A 1.635(10) . ? C6AW Cl7A 1.762(8) . ? C6AW H6A1 0.99 . ? C6AW H6A2 0.99 . ? Cl8B Cl8B 1.037(7) 3_657 ? 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 C22 Mn1 C20 87.84(19) . . ? C22 Mn1 C18 88.9(2) . . ? C20 Mn1 C18 91.3(2) . . ? C22 Mn1 N6 174.61(18) . . ? C20 Mn1 N6 96.55(17) . . ? C18 Mn1 N6 94.13(18) . . ? C22 Mn1 N12 96.48(18) . . ? C20 Mn1 N12 175.26(17) . . ? C18 Mn1 N12 90.71(18) . . ? N6 Mn1 N12 79.03(16) . . ? C22 Mn1 N1 91.12(18) . . ? C20 Mn1 N1 91.16(18) . . ? C18 Mn1 N1 177.53(18) . . ? N6 Mn1 N1 85.68(15) . . ? N12 Mn1 N1 86.83(14) . . ? C2 S3 C4 90.3(2) . . ? N1 C2 S3 114.5(3) . . ? N1 C2 H2 122.8 . . ? S3 C2 H2 122.8 . . ? C2 N1 C5 110.7(4) . . ? C2 N1 Mn1 124.3(3) . . ? C5 N1 Mn1 124.9(3) . . ? C4 C5 N1 114.3(4) . . ? C4 C5 H5 122.8 . . ? N1 C5 H5 122.8 . . ? C5 C4 S3 110.2(4) . . ? C5 C4 H4 124.9 . . ? S3 C4 H4 124.9 . . ? C7 N6 C11 117.9(4) . . ? C7 N6 Mn1 126.2(3) . . ? C11 N6 Mn1 115.8(3) . . ? N6 C7 C8 122.7(5) . . ? N6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C9 C8 C7 119.1(6) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 119.4(5) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 119.0(5) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N6 C11 C10 121.8(5) . . ? N6 C11 C13 114.3(4) . . ? C10 C11 C13 123.8(5) . . ? C13 N12 C17 118.3(4) . . ? C13 N12 Mn1 116.1(3) . . ? C17 N12 Mn1 125.5(3) . . ? N12 C13 C14 121.2(5) . . ? N12 C13 C11 114.6(4) . . ? C14 C13 C11 124.2(5) . . ? C15 C14 C13 119.4(5) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 119.7(5) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 118.6(6) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? N12 C17 C16 122.7(5) . . ? N12 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? O19 C18 Mn1 176.8(4) . . ? O21 C20 Mn1 178.3(4) . . ? O23 C22 Mn1 178.8(4) . . ? O4AW Cl1A O2AW 116.9(8) . . ? O4AW Cl1A O3AW 106.6(13) . . ? O2AW Cl1A O3AW 104.9(10) . . ? O4AW Cl1A O5AW 112.2(12) . . ? O2AW Cl1A O5AW 112.2(8) . . ? O3AW Cl1A O5AW 102.7(8) . . ? O3BW Cl1B O5BW 122.4(12) . . ? O3BW Cl1B O4BW 113.9(18) . . ? O5BW Cl1B O4BW 97.6(13) . . ? O5CW Cl1C O3CW 115.3(16) . . ? O5CW Cl1C O4CW 109(2) . . ? O3CW Cl1C O4CW 108.9(16) . . ? Cl8A C6AW Cl7A 115.7(5) . . ? Cl8A C6AW H6A1 108.4 . . ? Cl7A C6AW H6A1 108.4 . . ? Cl8A C6AW H6A2 108.4 . . ? Cl7A C6AW H6A2 108.4 . . ? H6A1 C6AW H6A2 107.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 S3 C2 N1 -0.8(3) . . . . ? S3 C2 N1 C5 1.1(5) . . . . ? S3 C2 N1 Mn1 -174.97(19) . . . . ? C22 Mn1 N1 C2 42.7(4) . . . . ? C20 Mn1 N1 C2 130.6(3) . . . . ? C18 Mn1 N1 C2 -47(4) . . . . ? N6 Mn1 N1 C2 -132.9(3) . . . . ? N12 Mn1 N1 C2 -53.7(3) . . . . ? C22 Mn1 N1 C5 -132.8(3) . . . . ? C20 Mn1 N1 C5 -44.9(3) . . . . ? C18 Mn1 N1 C5 137(4) . . . . ? N6 Mn1 N1 C5 51.6(3) . . . . ? N12 Mn1 N1 C5 130.8(3) . . . . ? C2 N1 C5 C4 -0.8(5) . . . . ? Mn1 N1 C5 C4 175.2(3) . . . . ? N1 C5 C4 S3 0.2(5) . . . . ? C2 S3 C4 C5 0.3(4) . . . . ? C22 Mn1 N6 C7 -145.5(18) . . . . ? C20 Mn1 N6 C7 -1.1(5) . . . . ? C18 Mn1 N6 C7 90.7(5) . . . . ? N12 Mn1 N6 C7 -179.4(5) . . . . ? N1 Mn1 N6 C7 -91.8(5) . . . . ? C22 Mn1 N6 C11 30(2) . . . . ? C20 Mn1 N6 C11 174.8(3) . . . . ? C18 Mn1 N6 C11 -93.4(4) . . . . ? N12 Mn1 N6 C11 -3.5(3) . . . . ? N1 Mn1 N6 C11 84.1(3) . . . . ? C11 N6 C7 C8 -0.4(9) . . . . ? Mn1 N6 C7 C8 175.5(5) . . . . ? N6 C7 C8 C9 0.7(10) . . . . ? C7 C8 C9 C10 0.7(10) . . . . ? C8 C9 C10 C11 -2.3(9) . . . . ? C7 N6 C11 C10 -1.3(7) . . . . ? Mn1 N6 C11 C10 -177.6(4) . . . . ? C7 N6 C11 C13 179.4(4) . . . . ? Mn1 N6 C11 C13 3.2(5) . . . . ? C9 C10 C11 N6 2.7(8) . . . . ? C9 C10 C11 C13 -178.2(5) . . . . ? C22 Mn1 N12 C13 -173.7(3) . . . . ? C20 Mn1 N12 C13 -18(2) . . . . ? C18 Mn1 N12 C13 97.3(3) . . . . ? N6 Mn1 N12 C13 3.3(3) . . . . ? N1 Mn1 N12 C13 -82.9(3) . . . . ? C22 Mn1 N12 C17 4.8(4) . . . . ? C20 Mn1 N12 C17 161(2) . . . . ? C18 Mn1 N12 C17 -84.2(4) . . . . ? N6 Mn1 N12 C17 -178.2(4) . . . . ? N1 Mn1 N12 C17 95.6(4) . . . . ? C17 N12 C13 C14 -0.6(6) . . . . ? Mn1 N12 C13 C14 178.0(3) . . . . ? C17 N12 C13 C11 178.8(4) . . . . ? Mn1 N12 C13 C11 -2.6(5) . . . . ? N6 C11 C13 N12 -0.4(6) . . . . ? C10 C11 C13 N12 -179.6(4) . . . . ? N6 C11 C13 C14 179.0(4) . . . . ? C10 C11 C13 C14 -0.2(7) . . . . ? N12 C13 C14 C15 0.4(7) . . . . ? C11 C13 C14 C15 -178.9(4) . . . . ? C13 C14 C15 C16 0.4(7) . . . . ? C14 C15 C16 C17 -0.9(7) . . . . ? C13 N12 C17 C16 0.0(7) . . . . ? Mn1 N12 C17 C16 -178.5(4) . . . . ? C15 C16 C17 N12 0.8(7) . . . . ? C22 Mn1 C18 O19 -39(8) . . . . ? C20 Mn1 C18 O19 -127(8) . . . . ? N6 Mn1 C18 O19 136(8) . . . . ? N12 Mn1 C18 O19 57(8) . . . . ? N1 Mn1 C18 O19 51(10) . . . . ? C22 Mn1 C20 O21 -1(17) . . . . ? C18 Mn1 C20 O21 88(17) . . . . ? N6 Mn1 C20 O21 -18E1(10) . . . . ? N12 Mn1 C20 O21 -156(15) . . . . ? N1 Mn1 C20 O21 -92(17) . . . . ? C20 Mn1 C22 O23 5E1(2) . . . . ? C18 Mn1 C22 O23 -4E1(2) . . . . ? N6 Mn1 C22 O23 -16E1(2) . . . . ? N12 Mn1 C22 O23 -13E1(2) . . . . ? N1 Mn1 C22 O23 14E1(2) . . . . ? #===END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-15 at 11:55:14 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : d:\xprogs\wingx\wingx\files\archive.dat # CIF files read : jv04bk1n struct data_6b _database_code_depnum_ccdc_archive 'CCDC 716674' _audit_creation_date 2008-04-15T11:55:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H11 Mn N3 O3 S, F6 P' _chemical_formula_sum 'C16 H11 F6 Mn N3 O3 P S' _chemical_formula_weight 525.25 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6199(3) _cell_length_b 10.0390(3) _cell_length_c 11.5074(3) _cell_angle_alpha 78.4870(10) _cell_angle_beta 80.485(2) _cell_angle_gamma 84.597(2) _cell_volume 960.41(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1958 _cell_measurement_theta_min 3.011 _cell_measurement_theta_max 27.049 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.816 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.79407 _exptl_absorpt_correction_T_max 0.9 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'BrukerAXS ApexII-CCD area detector ' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_number 15455 _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 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3935 _reflns_number_gt 3416 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0253P)^2^+0.5029P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3935 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0624 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.315 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.06 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Mn1 Mn 0.19658(3) 0.27666(3) 0.17380(2) 0.01393(8) Uani 1 1 d . . . N31 N 0.40713(17) 0.22115(14) 0.08002(13) 0.0149(3) Uani 1 1 d . . . C32 C 0.4668(2) 0.28137(18) -0.03176(17) 0.0196(4) Uani 1 1 d . . . H32 H 0.4078 0.3564 -0.0715 0.024 Uiso 1 1 calc R . . C3 C 0.6089(2) 0.23926(19) -0.09094(17) 0.0200(4) Uani 1 1 d . . . H3 H 0.6468 0.2847 -0.1698 0.024 Uiso 1 1 calc R . . C34 C 0.6964(2) 0.13004(19) -0.03470(17) 0.0190(4) Uani 1 1 d . . . H34 H 0.7961 0.1006 -0.0734 0.023 Uiso 1 1 calc R . . C35 C 0.6355(2) 0.06445(18) 0.07932(16) 0.0177(4) Uani 1 1 d . . . H35 H 0.6925 -0.0115 0.1197 0.021 Uiso 1 1 calc R . . C6 C 0.4906(2) 0.11105(17) 0.13371(16) 0.0148(4) Uani 1 1 d . . . C7 C 0.4132(2) 0.04788(17) 0.25331(16) 0.0141(4) Uani 1 1 d . . . C8 C 0.4813(2) -0.06095(18) 0.32603(16) 0.0190(4) Uani 1 1 d . . . H8 H 0.5814 -0.1013 0.2987 0.023 Uiso 1 1 calc R . . C9 C 0.4021(2) -0.11033(18) 0.43894(17) 0.0205(4) Uani 1 1 d . . . H9 H 0.4468 -0.1849 0.4903 0.025 Uiso 1 1 calc R . . C10 C 0.2572(2) -0.04943(19) 0.47560(17) 0.0210(4) Uani 1 1 d . . . H10 H 0.2012 -0.0806 0.5532 0.025 Uiso 1 1 calc R . . C11 C 0.1944(2) 0.05751(18) 0.39828(17) 0.0188(4) Uani 1 1 d . . . H11 H 0.0937 0.0979 0.4241 0.023 Uiso 1 1 calc R . . N12 N 0.26911(17) 0.10712(14) 0.28835(13) 0.0150(3) Uani 1 1 d . . . C2 C 0.3091(2) 0.38345(17) 0.26259(15) 0.0147(4) Uani 1 1 d . . . N1 N 0.2473(2) 0.46571(15) 0.33831(14) 0.0172(3) Uani 1 1 d . . . C5 C 0.3490(2) 0.53248(19) 0.38535(16) 0.0199(4) Uani 1 1 d . . . H5 H 0.3155 0.593 0.4397 0.024 Uiso 1 1 calc R . . C4 C 0.5001(2) 0.50133(19) 0.34484(17) 0.0215(4) Uani 1 1 d . . . H4 H 0.5882 0.5364 0.3657 0.026 Uiso 1 1 calc R . . S3 S 0.51042(5) 0.38766(5) 0.24893(4) 0.01857(11) Uani 1 1 d . . . C18 C 0.1687(2) 0.43648(19) 0.07174(17) 0.0182(4) Uani 1 1 d . . . O19 O 0.15860(16) 0.53968(13) 0.00818(13) 0.0263(3) Uani 1 1 d . . . C20 C 0.0956(2) 0.18398(18) 0.08822(17) 0.0191(4) Uani 1 1 d . . . O21 O 0.02849(17) 0.13130(14) 0.03483(14) 0.0309(3) Uani 1 1 d . . . C22 C 0.0052(2) 0.30402(17) 0.25976(17) 0.0180(4) Uani 1 1 d . . . O23 O -0.12177(15) 0.31588(13) 0.30868(13) 0.0252(3) Uani 1 1 d . . . P1 P 0.09452(6) 0.26766(5) 0.66706(4) 0.01992(12) Uani 1 1 d . . . F1 F 0.24909(13) 0.25606(12) 0.57025(10) 0.0280(3) Uani 1 1 d . . . F2 F 0.08819(14) 0.43092(11) 0.62536(11) 0.0326(3) Uani 1 1 d . . . F3 F -0.05849(14) 0.28303(14) 0.76275(12) 0.0415(3) Uani 1 1 d . . . F4 F 0.10165(15) 0.10626(12) 0.70678(14) 0.0462(4) Uani 1 1 d . . . F5 F 0.20437(15) 0.27762(15) 0.76352(11) 0.0409(3) Uani 1 1 d . . . F6 F -0.01296(15) 0.26083(14) 0.56836(13) 0.0432(3) Uani 1 1 d . . . H1 H 0.154(3) 0.479(2) 0.355(2) 0.029(7) Uiso 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 Mn1 0.01019(14) 0.01266(14) 0.01856(16) 0.00018(11) -0.00495(11) -0.00055(10) N31 0.0145(7) 0.0139(7) 0.0164(8) 0.0003(6) -0.0059(6) -0.0015(6) C32 0.0179(10) 0.0181(9) 0.0212(10) 0.0027(8) -0.0060(8) -0.0011(7) C3 0.0194(10) 0.0232(10) 0.0154(9) 0.0017(7) -0.0020(8) -0.0030(8) C34 0.0139(9) 0.0225(9) 0.0205(10) -0.0047(8) -0.0015(8) -0.0014(7) C35 0.0162(9) 0.0181(9) 0.0189(10) -0.0012(7) -0.0069(8) 0.0015(7) C6 0.0145(9) 0.0141(8) 0.0172(9) -0.0030(7) -0.0068(7) -0.0004(7) C7 0.0126(9) 0.0147(8) 0.0158(9) -0.0033(7) -0.0037(7) -0.0007(7) C8 0.0190(10) 0.0176(9) 0.0193(10) -0.0017(7) -0.0044(8) 0.0029(7) C9 0.0236(10) 0.0168(9) 0.0199(10) 0.0028(7) -0.0075(8) -0.0011(8) C10 0.0194(10) 0.0218(9) 0.0194(10) 0.0033(8) -0.0013(8) -0.0068(8) C11 0.0133(9) 0.0182(9) 0.0227(10) 0.0011(8) -0.0016(8) -0.0020(7) N12 0.0134(8) 0.0135(7) 0.0181(8) -0.0009(6) -0.0039(6) -0.0024(6) C2 0.0139(9) 0.0127(8) 0.0156(9) 0.0045(7) -0.0050(7) -0.0012(7) N1 0.0150(9) 0.0181(8) 0.0176(8) -0.0001(6) -0.0041(7) 0.0004(6) C5 0.0255(11) 0.0193(9) 0.0153(10) -0.0012(7) -0.0059(8) -0.0029(8) C4 0.0252(11) 0.0221(10) 0.0183(10) 0.0015(8) -0.0096(8) -0.0076(8) S3 0.0130(2) 0.0206(2) 0.0219(3) -0.00106(18) -0.00456(19) -0.00312(17) C18 0.0112(9) 0.0209(10) 0.0238(10) -0.0047(8) -0.0060(8) -0.0009(7) O19 0.0234(8) 0.0197(7) 0.0334(8) 0.0064(6) -0.0115(6) -0.0013(6) C20 0.0151(9) 0.0158(9) 0.0252(10) -0.0001(8) -0.0056(8) 0.0024(7) O21 0.0289(8) 0.0279(8) 0.0431(9) -0.0123(7) -0.0198(7) -0.0005(6) C22 0.0166(10) 0.0144(9) 0.0228(10) 0.0007(7) -0.0072(8) -0.0018(7) O23 0.0130(7) 0.0264(7) 0.0337(8) -0.0023(6) -0.0006(6) -0.0005(5) P1 0.0153(3) 0.0193(2) 0.0213(3) 0.0028(2) -0.0012(2) 0.00146(19) F1 0.0238(6) 0.0308(6) 0.0223(6) 0.0012(5) 0.0026(5) 0.0096(5) F2 0.0284(7) 0.0186(6) 0.0440(8) -0.0004(5) 0.0054(6) 0.0035(5) F3 0.0221(7) 0.0472(8) 0.0386(8) 0.0127(6) 0.0126(6) 0.0087(6) F4 0.0327(7) 0.0212(6) 0.0718(10) 0.0143(6) -0.0002(7) 0.0009(5) F5 0.0306(7) 0.0667(9) 0.0272(7) -0.0138(6) -0.0107(6) 0.0096(6) F6 0.0334(8) 0.0479(8) 0.0562(9) -0.0175(7) -0.0256(7) 0.0071(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Mn1 C22 1.805(2) . ? Mn1 C18 1.8111(19) . ? Mn1 C20 1.8426(18) . ? Mn1 C2 2.0235(17) . ? Mn1 N31 2.0423(15) . ? Mn1 N12 2.0499(14) . ? N31 C32 1.347(2) . ? N31 C6 1.358(2) . ? C32 C3 1.373(3) . ? C32 H32 0.95 . ? C3 C34 1.383(3) . ? C3 H3 0.95 . ? C34 C35 1.387(3) . ? C34 H34 0.95 . ? C35 C6 1.386(3) . ? C35 H35 0.95 . ? C6 C7 1.473(2) . ? C7 N12 1.360(2) . ? C7 C8 1.384(2) . ? C8 C9 1.383(3) . ? C8 H8 0.95 . ? C9 C10 1.377(3) . ? C9 H9 0.95 . ? C10 C11 1.381(3) . ? C10 H10 0.95 . ? C11 N12 1.343(2) . ? C11 H11 0.95 . ? C2 N1 1.333(2) . ? C2 S3 1.7201(18) . ? N1 C5 1.387(2) . ? N1 H1 0.80(2) . ? C5 C4 1.339(3) . ? C5 H5 0.95 . ? C4 S3 1.7260(19) . ? C4 H4 0.95 . ? C18 O19 1.148(2) . ? C20 O21 1.139(2) . ? C22 O23 1.152(2) . ? P1 F3 1.5891(13) . ? P1 F4 1.5915(13) . ? P1 F6 1.5950(13) . ? P1 F5 1.5963(13) . ? P1 F1 1.6005(12) . ? P1 F2 1.6117(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 C22 Mn1 C18 90.81(8) . . ? C22 Mn1 C20 86.26(8) . . ? C18 Mn1 C20 92.17(8) . . ? C22 Mn1 C2 94.53(8) . . ? C18 Mn1 C2 85.99(7) . . ? C20 Mn1 C2 178.01(7) . . ? C22 Mn1 N31 172.97(7) . . ? C18 Mn1 N31 94.67(7) . . ? C20 Mn1 N31 89.12(7) . . ? C2 Mn1 N31 90.25(6) . . ? C22 Mn1 N12 96.75(7) . . ? C18 Mn1 N12 169.40(7) . . ? C20 Mn1 N12 95.71(7) . . ? C2 Mn1 N12 86.02(6) . . ? N31 Mn1 N12 78.42(6) . . ? C32 N31 C6 117.61(16) . . ? C32 N31 Mn1 125.46(12) . . ? C6 N31 Mn1 116.88(12) . . ? N31 C32 C3 123.01(17) . . ? N31 C32 H32 118.5 . . ? C3 C32 H32 118.5 . . ? C32 C3 C34 119.36(17) . . ? C32 C3 H3 120.3 . . ? C34 C3 H3 120.3 . . ? C3 C34 C35 118.60(18) . . ? C3 C34 H34 120.7 . . ? C35 C34 H34 120.7 . . ? C6 C35 C34 119.23(17) . . ? C6 C35 H35 120.4 . . ? C34 C35 H35 120.4 . . ? N31 C6 C35 122.12(16) . . ? N31 C6 C7 113.93(15) . . ? C35 C6 C7 123.95(16) . . ? N12 C7 C8 122.18(16) . . ? N12 C7 C6 114.44(15) . . ? C8 C7 C6 123.37(16) . . ? C9 C8 C7 119.26(18) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 118.81(17) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 119.20(18) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? N12 C11 C10 123.03(17) . . ? N12 C11 H11 118.5 . . ? C10 C11 H11 118.5 . . ? C11 N12 C7 117.51(15) . . ? C11 N12 Mn1 125.97(12) . . ? C7 N12 Mn1 116.23(12) . . ? N1 C2 S3 106.44(13) . . ? N1 C2 Mn1 128.66(13) . . ? S3 C2 Mn1 124.87(10) . . ? C2 N1 C5 118.32(17) . . ? C2 N1 H1 121.3(16) . . ? C5 N1 H1 120.3(16) . . ? C4 C5 N1 111.80(17) . . ? C4 C5 H5 124.1 . . ? N1 C5 H5 124.1 . . ? C5 C4 S3 109.58(14) . . ? C5 C4 H4 125.2 . . ? S3 C4 H4 125.2 . . ? C2 S3 C4 93.86(9) . . ? O19 C18 Mn1 176.32(16) . . ? O21 C20 Mn1 177.07(16) . . ? O23 C22 Mn1 174.42(16) . . ? F3 P1 F4 91.27(7) . . ? F3 P1 F6 90.35(8) . . ? F4 P1 F6 91.00(8) . . ? F3 P1 F5 90.53(7) . . ? F4 P1 F5 90.17(8) . . ? F6 P1 F5 178.52(8) . . ? F3 P1 F1 178.61(7) . . ? F4 P1 F1 90.08(7) . . ? F6 P1 F1 89.94(7) . . ? F5 P1 F1 89.15(7) . . ? F3 P1 F2 89.28(7) . . ? F4 P1 F2 179.36(8) . . ? F6 P1 F2 88.68(7) . . ? F5 P1 F2 90.14(7) . . ? F1 P1 F2 89.37(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Mn1 N31 C32 -12.41(15) . . . . ? C20 Mn1 N31 C32 79.70(15) . . . . ? C2 Mn1 N31 C32 -98.41(15) . . . . ? N12 Mn1 N31 C32 175.71(15) . . . . ? C18 Mn1 N31 C6 170.18(12) . . . . ? C20 Mn1 N31 C6 -97.71(13) . . . . ? C2 Mn1 N31 C6 84.18(12) . . . . ? N12 Mn1 N31 C6 -1.70(11) . . . . ? C6 N31 C32 C3 -2.3(3) . . . . ? Mn1 N31 C32 C3 -179.64(13) . . . . ? N31 C32 C3 C34 0.1(3) . . . . ? C32 C3 C34 C35 1.4(3) . . . . ? C3 C34 C35 C6 -0.7(3) . . . . ? C32 N31 C6 C35 2.9(2) . . . . ? Mn1 N31 C6 C35 -179.46(12) . . . . ? C32 N31 C6 C7 -177.28(15) . . . . ? Mn1 N31 C6 C7 0.33(18) . . . . ? C34 C35 C6 N31 -1.5(3) . . . . ? C34 C35 C6 C7 178.76(16) . . . . ? N31 C6 C7 N12 2.1(2) . . . . ? C35 C6 C7 N12 -178.09(15) . . . . ? N31 C6 C7 C8 -176.58(15) . . . . ? C35 C6 C7 C8 3.2(3) . . . . ? N12 C7 C8 C9 -1.0(3) . . . . ? C6 C7 C8 C9 177.60(16) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 N12 -1.0(3) . . . . ? C10 C11 N12 C7 0.0(3) . . . . ? C10 C11 N12 Mn1 -173.50(13) . . . . ? C8 C7 N12 C11 1.0(2) . . . . ? C6 C7 N12 C11 -177.72(15) . . . . ? C8 C7 N12 Mn1 175.13(13) . . . . ? C6 C7 N12 Mn1 -3.59(18) . . . . ? C22 Mn1 N12 C11 -8.70(15) . . . . ? C18 Mn1 N12 C11 126.6(4) . . . . ? C20 Mn1 N12 C11 -95.60(15) . . . . ? C2 Mn1 N12 C11 85.40(15) . . . . ? N31 Mn1 N12 C11 176.48(15) . . . . ? C22 Mn1 N12 C7 177.74(12) . . . . ? C18 Mn1 N12 C7 -47.0(4) . . . . ? C20 Mn1 N12 C7 90.84(13) . . . . ? C2 Mn1 N12 C7 -88.16(12) . . . . ? N31 Mn1 N12 C7 2.91(11) . . . . ? C22 Mn1 C2 N1 -12.15(17) . . . . ? C18 Mn1 C2 N1 78.35(16) . . . . ? N31 Mn1 C2 N1 173.01(16) . . . . ? N12 Mn1 C2 N1 -108.62(16) . . . . ? C22 Mn1 C2 S3 170.04(11) . . . . ? C18 Mn1 C2 S3 -99.46(12) . . . . ? N31 Mn1 C2 S3 -4.80(11) . . . . ? N12 Mn1 C2 S3 73.57(11) . . . . ? S3 C2 N1 C5 0.48(19) . . . . ? Mn1 C2 N1 C5 -177.64(13) . . . . ? C2 N1 C5 C4 -0.1(2) . . . . ? N1 C5 C4 S3 -0.3(2) . . . . ? N1 C2 S3 C4 -0.56(13) . . . . ? Mn1 C2 S3 C4 177.66(11) . . . . ? C5 C4 S3 C2 0.53(15) . . . . ? #===END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-03-28 at 17:22:46 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : e:\xprogs\wingx\files\archive.dat # CIF files read : jv02bk1n struct data_7b _database_code_depnum_ccdc_archive 'CCDC 716675' _audit_creation_date 2008-03-28T17:22:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H25 Au Mn N3 O3 P S, F6 P' _chemical_formula_sum 'C34 H25 Au F6 Mn N3 O3 P2 S' _chemical_formula_weight 983.48 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0938(3) _cell_length_b 11.4700(4) _cell_length_c 15.1096(5) _cell_angle_alpha 94.041(2) _cell_angle_beta 101.191(2) _cell_angle_gamma 112.355(2) _cell_volume 1722.13(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1940 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 27.36 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.5293 _exptl_absorpt_correction_T_max 0.71035 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_unetI/netI 0.0599 _diffrn_reflns_number 57416 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.58 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 7802 _reflns_number_gt 6738 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'DIRDIF99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0180P)^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_number_reflns 7802 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0519 _refine_ls_wR_factor_gt 0.0493 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.776 _refine_diff_density_min -0.824 _refine_diff_density_rms 0.146 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Mn1 Mn 0.39907(5) 0.73796(4) 0.31310(3) 0.01166(12) Uani 1 1 d . . . N51 N 0.2763(3) 0.6233(2) 0.38504(18) 0.0120(6) Uani 1 1 d . . . C1 C 0.1415(3) 0.5659(3) 0.3589(2) 0.0135(8) Uani 1 1 d . . . H1 H 0.0975 0.5866 0.3074 0.016 Uiso 1 1 calc R . . C52 C 0.0660(3) 0.4779(3) 0.4051(2) 0.0157(8) Uani 1 1 d . . . H2 H -0.0271 0.4407 0.3856 0.019 Uiso 1 1 calc R . . C3 C 0.1305(3) 0.4456(3) 0.4810(2) 0.0160(8) Uani 1 1 d . . . H3 H 0.0817 0.3834 0.5116 0.019 Uiso 1 1 calc R . . C54 C 0.2678(3) 0.5064(3) 0.5107(2) 0.0145(8) Uani 1 1 d . . . H54 H 0.3125 0.4879 0.5628 0.017 Uiso 1 1 calc R . . C55 C 0.3394(3) 0.5962(3) 0.4620(2) 0.0121(7) Uani 1 1 d . . . C6 C 0.4848(3) 0.6725(3) 0.4899(2) 0.0126(7) Uani 1 1 d . . . C7 C 0.5658(3) 0.6713(3) 0.5716(2) 0.0176(8) Uani 1 1 d . . . H7 H 0.53 0.6155 0.6106 0.021 Uiso 1 1 calc R . . C8 C 0.7004(3) 0.7534(3) 0.5953(2) 0.0187(8) Uani 1 1 d . . . H8 H 0.7557 0.7546 0.6505 0.022 Uiso 1 1 calc R . . C9 C 0.7505(3) 0.8335(3) 0.5348(2) 0.0162(8) Uani 1 1 d . . . H9 H 0.8404 0.8899 0.5487 0.019 Uiso 1 1 calc R . . C10 C 0.6656(3) 0.8285(3) 0.4538(2) 0.0154(8) Uani 1 1 d . . . H10 H 0.7009 0.8811 0.413 0.018 Uiso 1 1 calc R . . N2 N 0.5342(3) 0.7515(2) 0.43053(18) 0.0117(6) Uani 1 1 d . . . C11 C 0.3838(3) 0.8817(3) 0.3581(2) 0.0176(8) Uani 1 1 d . . . O1 O 0.3845(2) 0.9772(2) 0.38685(18) 0.0276(6) Uani 1 1 d . . . C12 C 0.5155(3) 0.8383(3) 0.2529(2) 0.0154(8) Uani 1 1 d . . . O2 O 0.5825(3) 0.9029(2) 0.21222(17) 0.0249(6) Uani 1 1 d . . . C13 C 0.2682(4) 0.7084(3) 0.2109(3) 0.0159(8) Uani 1 1 d . . . O3 O 0.1892(3) 0.6889(2) 0.14443(18) 0.0249(6) Uani 1 1 d . . . N1 N 0.4319(3) 0.5795(2) 0.26474(18) 0.0114(6) Uani 1 1 d . . . C5 C 0.5635(3) 0.5965(3) 0.2672(2) 0.0137(7) Uani 1 1 d . . . H5 H 0.636 0.6732 0.2928 0.016 Uiso 1 1 calc R . . C4 C 0.5790(3) 0.4943(3) 0.2300(2) 0.0156(8) Uani 1 1 d . . . H4 H 0.6607 0.4912 0.2268 0.019 Uiso 1 1 calc R . . S3 S 0.42558(9) 0.37191(8) 0.18965(6) 0.0158(2) Uani 1 1 d . . . C2 C 0.3430(3) 0.4630(3) 0.2239(2) 0.0122(7) Uani 1 1 d . . . Au1 Au 0.138316(13) 0.379566(12) 0.191562(9) 0.01134(4) Uani 1 1 d . . . P1 P -0.09040(9) 0.26463(8) 0.14861(6) 0.01152(19) Uani 1 1 d . . . C17 C -0.1612(3) 0.2159(3) 0.2456(2) 0.0119(7) Uani 1 1 d . . . C18 C -0.2744(3) 0.2337(3) 0.2597(2) 0.0153(8) Uani 1 1 d . . . H18 H -0.3203 0.2649 0.2161 0.018 Uiso 1 1 calc R . . C19 C -0.3186(4) 0.2051(3) 0.3382(2) 0.0221(9) Uani 1 1 d . . . H19 H -0.3945 0.2165 0.3467 0.027 Uiso 1 1 calc R . . C20 C -0.2508(4) 0.1598(3) 0.4040(2) 0.0203(8) Uani 1 1 d . . . H20 H -0.2792 0.1432 0.4575 0.024 Uiso 1 1 calc R . . C21 C -0.1400(3) 0.1391(3) 0.3899(2) 0.0176(8) Uani 1 1 d . . . H21 H -0.0957 0.1062 0.4333 0.021 Uiso 1 1 calc R . . C22 C -0.0956(3) 0.1675(3) 0.3113(2) 0.0146(7) Uani 1 1 d . . . H22 H -0.0209 0.1541 0.3025 0.017 Uiso 1 1 calc R . . C23 C -0.1898(3) 0.3413(3) 0.0885(2) 0.0125(7) Uani 1 1 d . . . C24 C -0.3196(3) 0.2695(3) 0.0361(2) 0.0191(8) Uani 1 1 d . . . H24 H -0.3548 0.1809 0.0298 0.023 Uiso 1 1 calc R . . C25 C -0.3964(4) 0.3295(4) -0.0065(2) 0.0257(9) Uani 1 1 d . . . H25 H -0.4833 0.2812 -0.0409 0.031 Uiso 1 1 calc R . . C26 C -0.3440(4) 0.4618(4) 0.0019(3) 0.0279(10) Uani 1 1 d . . . H26 H -0.3955 0.502 -0.0273 0.034 Uiso 1 1 calc R . . C27 C -0.2155(4) 0.5334(4) 0.0537(3) 0.0290(10) Uani 1 1 d . . . H27 H -0.1808 0.622 0.0598 0.035 Uiso 1 1 calc R . . C28 C -0.1381(4) 0.4736(3) 0.0968(2) 0.0205(8) Uani 1 1 d . . . H28 H -0.0513 0.5223 0.1313 0.025 Uiso 1 1 calc R . . C29 C -0.1301(3) 0.1214(3) 0.0697(2) 0.0127(7) Uani 1 1 d . . . C30 C -0.1871(3) -0.0012(3) 0.0901(2) 0.0188(8) Uani 1 1 d . . . H30 H -0.2087 -0.0134 0.1462 0.023 Uiso 1 1 calc R . . C31 C -0.2115(4) -0.1051(3) 0.0262(3) 0.0274(10) Uani 1 1 d . . . H31 H -0.2483 -0.1873 0.0398 0.033 Uiso 1 1 calc R . . C32 C -0.1814(4) -0.0870(4) -0.0574(3) 0.0287(10) Uani 1 1 d . . . H32 H -0.1991 -0.1573 -0.1003 0.034 Uiso 1 1 calc R . . C33 C -0.1251(4) 0.0348(4) -0.0783(2) 0.0253(9) Uani 1 1 d . . . H33 H -0.1045 0.0466 -0.1347 0.03 Uiso 1 1 calc R . . C34 C -0.0998(3) 0.1382(3) -0.0148(2) 0.0179(8) Uani 1 1 d . . . H34 H -0.0619 0.2202 -0.0284 0.021 Uiso 1 1 calc R . . P2 P 0.03277(9) 0.18231(9) 0.68684(7) 0.0186(2) Uani 1 1 d . . . F1 F 0.1177(2) 0.3210(2) 0.66689(17) 0.0436(6) Uani 1 1 d . . . F2 F -0.0518(2) 0.04317(18) 0.70646(14) 0.0270(5) Uani 1 1 d . . . F3 F 0.0645(3) 0.1183(2) 0.60162(16) 0.0527(8) Uani 1 1 d . . . F4 F 0.1634(2) 0.1826(2) 0.75229(18) 0.0543(8) Uani 1 1 d . . . F5 F -0.0028(3) 0.2446(2) 0.76961(15) 0.0477(7) Uani 1 1 d . . . F6 F -0.0968(2) 0.1822(2) 0.61920(15) 0.0335(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0107(3) 0.0117(3) 0.0134(3) 0.0034(2) 0.0045(2) 0.0044(2) N51 0.0138(16) 0.0102(14) 0.0132(16) 0.0004(12) 0.0039(13) 0.0060(13) C1 0.0128(19) 0.0145(17) 0.0124(18) -0.0010(15) 0.0029(15) 0.0052(16) C52 0.0129(19) 0.0141(18) 0.017(2) -0.0028(15) 0.0052(16) 0.0022(16) C3 0.022(2) 0.0124(17) 0.015(2) 0.0040(15) 0.0099(17) 0.0058(16) C54 0.018(2) 0.0154(18) 0.0109(18) 0.0025(15) 0.0043(16) 0.0076(16) C55 0.0134(19) 0.0127(17) 0.0116(18) -0.0020(14) 0.0031(15) 0.0075(15) C6 0.0138(19) 0.0118(17) 0.0150(19) 0.0019(15) 0.0074(16) 0.0063(15) C7 0.018(2) 0.0215(19) 0.016(2) 0.0032(16) 0.0058(17) 0.0095(17) C8 0.016(2) 0.024(2) 0.015(2) -0.0031(16) -0.0026(16) 0.0100(17) C9 0.0093(18) 0.0137(18) 0.020(2) -0.0035(16) 0.0006(16) 0.0009(15) C10 0.013(2) 0.0126(17) 0.019(2) 0.0019(15) 0.0050(16) 0.0040(16) N2 0.0122(16) 0.0100(14) 0.0129(15) 0.0006(12) 0.0044(13) 0.0041(13) C11 0.014(2) 0.0199(19) 0.019(2) 0.0069(16) 0.0067(16) 0.0049(16) O1 0.0277(16) 0.0186(14) 0.0427(18) 0.0027(12) 0.0159(14) 0.0127(13) C12 0.0145(19) 0.0172(18) 0.0149(19) -0.0018(16) 0.0006(16) 0.0088(16) O2 0.0256(15) 0.0226(14) 0.0276(16) 0.0081(12) 0.0177(13) 0.0047(12) C13 0.013(2) 0.0141(18) 0.024(2) 0.0099(16) 0.0102(18) 0.0055(16) O3 0.0196(15) 0.0341(16) 0.0203(15) 0.0122(13) 0.0011(13) 0.0104(13) N1 0.0111(15) 0.0127(14) 0.0113(15) 0.0043(12) 0.0052(13) 0.0042(13) C5 0.0085(18) 0.0147(17) 0.0141(19) 0.0021(15) 0.0006(15) 0.0017(15) C4 0.0114(19) 0.0197(18) 0.0162(19) 0.0029(15) 0.0048(16) 0.0061(16) S3 0.0135(5) 0.0144(4) 0.0187(5) -0.0011(4) 0.0039(4) 0.0052(4) C2 0.0132(19) 0.0153(18) 0.0106(18) 0.0051(14) 0.0032(15) 0.0078(16) Au1 0.00939(7) 0.01099(7) 0.01252(8) 0.00134(5) 0.00235(5) 0.00311(5) P1 0.0103(5) 0.0113(4) 0.0122(5) 0.0024(4) 0.0027(4) 0.0035(4) C17 0.0106(18) 0.0112(16) 0.0116(18) 0.0003(14) 0.0024(15) 0.0025(15) C18 0.0159(19) 0.0149(17) 0.017(2) 0.0026(15) 0.0043(16) 0.0084(16) C19 0.022(2) 0.023(2) 0.024(2) -0.0011(17) 0.0116(18) 0.0099(18) C20 0.025(2) 0.022(2) 0.016(2) 0.0044(16) 0.0111(17) 0.0075(18) C21 0.018(2) 0.0130(18) 0.017(2) 0.0043(15) -0.0006(16) 0.0027(16) C22 0.0114(19) 0.0142(17) 0.0148(19) 0.0035(15) 0.0011(15) 0.0024(15) C23 0.0146(19) 0.0143(17) 0.0116(18) 0.0056(14) 0.0070(15) 0.0067(15) C24 0.015(2) 0.023(2) 0.017(2) 0.0002(16) 0.0028(17) 0.0068(17) C25 0.019(2) 0.048(3) 0.014(2) 0.0063(19) 0.0014(17) 0.020(2) C26 0.033(3) 0.050(3) 0.024(2) 0.025(2) 0.016(2) 0.033(2) C27 0.031(3) 0.029(2) 0.040(3) 0.022(2) 0.018(2) 0.018(2) C28 0.015(2) 0.0190(19) 0.029(2) 0.0070(17) 0.0089(18) 0.0063(17) C29 0.0092(18) 0.0115(17) 0.0148(19) -0.0021(14) -0.0011(15) 0.0041(15) C30 0.015(2) 0.0181(19) 0.024(2) 0.0015(16) 0.0110(17) 0.0045(16) C31 0.019(2) 0.0131(18) 0.048(3) -0.0008(18) 0.017(2) 0.0015(17) C32 0.016(2) 0.027(2) 0.034(3) -0.0159(19) 0.0012(19) 0.0047(18) C33 0.024(2) 0.036(2) 0.014(2) -0.0019(18) 0.0034(17) 0.013(2) C34 0.017(2) 0.0219(19) 0.015(2) 0.0031(16) 0.0045(16) 0.0076(17) P2 0.0144(5) 0.0230(5) 0.0190(5) 0.0067(4) 0.0054(4) 0.0070(4) F1 0.0233(13) 0.0393(14) 0.0525(17) 0.0314(13) -0.0024(12) -0.0029(11) F2 0.0306(13) 0.0156(11) 0.0298(13) 0.0026(9) 0.0102(11) 0.0027(10) F3 0.084(2) 0.0737(18) 0.0439(16) 0.0305(14) 0.0469(16) 0.0594(17) F4 0.0171(13) 0.0642(18) 0.0669(19) 0.0486(15) -0.0089(13) 0.0030(13) F5 0.086(2) 0.0292(13) 0.0292(14) -0.0037(11) 0.0246(14) 0.0204(14) F6 0.0188(12) 0.0361(13) 0.0414(15) 0.0067(11) -0.0043(11) 0.0119(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Mn1 C13 1.813(4) . ? Mn1 C12 1.814(4) . ? Mn1 C11 1.819(3) . ? Mn1 N2 2.042(3) . ? Mn1 N51 2.045(3) . ? Mn1 N1 2.095(2) . ? N51 C1 1.346(4) . ? N51 C55 1.356(4) . ? C1 C52 1.376(5) . ? C1 H1 0.93 . ? C52 C3 1.381(5) . ? C52 H2 0.93 . ? C3 C54 1.375(5) . ? C3 H3 0.93 . ? C54 C55 1.394(5) . ? C54 H54 0.93 . ? C55 C6 1.468(5) . ? C6 N2 1.362(4) . ? C6 C7 1.383(5) . ? C7 C8 1.386(5) . ? C7 H7 0.93 . ? C8 C9 1.386(5) . ? C8 H8 0.93 . ? C9 C10 1.374(5) . ? C9 H9 0.93 . ? C10 N2 1.344(4) . ? C10 H10 0.93 . ? C11 O1 1.146(4) . ? C12 O2 1.141(4) . ? C13 O3 1.143(4) . ? N1 C2 1.336(4) . ? N1 C5 1.390(4) . ? C5 C4 1.348(4) . ? C5 H5 0.93 . ? C4 S3 1.702(3) . ? C4 H4 0.93 . ? S3 C2 1.742(3) . ? C2 Au1 2.040(3) . ? Au1 P1 2.3007(9) . ? P1 C23 1.810(3) . ? P1 C29 1.812(3) . ? P1 C17 1.817(3) . ? C17 C22 1.389(5) . ? C17 C18 1.399(4) . ? C18 C19 1.383(5) . ? C18 H18 0.93 . ? C19 C20 1.380(5) . ? C19 H19 0.93 . ? C20 C21 1.388(4) . ? C20 H20 0.93 . ? C21 C22 1.386(4) . ? C21 H21 0.93 . ? C22 H22 0.93 . ? C23 C28 1.390(4) . ? C23 C24 1.394(5) . ? C24 C25 1.381(5) . ? C24 H24 0.93 . ? C25 C26 1.389(5) . ? C25 H25 0.93 . ? C26 C27 1.380(6) . ? C26 H26 0.93 . ? C27 C28 1.388(5) . ? C27 H27 0.93 . ? C28 H28 0.93 . ? C29 C30 1.391(4) . ? C29 C34 1.390(5) . ? C30 C31 1.384(4) . ? C30 H30 0.93 . ? C31 C32 1.379(5) . ? C31 H31 0.93 . ? C32 C33 1.384(5) . ? C32 H32 0.93 . ? C33 C34 1.374(4) . ? C33 H33 0.93 . ? C34 H34 0.93 . ? P2 F5 1.584(2) . ? P2 F4 1.587(2) . ? P2 F6 1.593(2) . ? P2 F1 1.596(2) . ? P2 F2 1.597(2) . ? P2 F3 1.600(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 C13 Mn1 C12 86.96(15) . . ? C13 Mn1 C11 92.39(15) . . ? C12 Mn1 C11 86.97(14) . . ? C13 Mn1 N2 173.70(13) . . ? C12 Mn1 N2 98.46(13) . . ? C11 Mn1 N2 91.12(13) . . ? C13 Mn1 N51 95.82(13) . . ? C12 Mn1 N51 176.90(13) . . ? C11 Mn1 N51 94.27(12) . . ? N2 Mn1 N51 78.69(11) . . ? C13 Mn1 N1 90.81(12) . . ? C12 Mn1 N1 90.52(12) . . ? C11 Mn1 N1 175.82(14) . . ? N2 Mn1 N1 85.94(10) . . ? N51 Mn1 N1 88.08(10) . . ? C1 N51 C55 118.4(3) . . ? C1 N51 Mn1 125.8(2) . . ? C55 N51 Mn1 115.6(2) . . ? N51 C1 C52 122.6(3) . . ? N51 C1 H1 118.7 . . ? C52 C1 H1 118.7 . . ? C1 C52 C3 119.1(3) . . ? C1 C52 H2 120.5 . . ? C3 C52 H2 120.5 . . ? C54 C3 C52 119.1(3) . . ? C54 C3 H3 120.4 . . ? C52 C3 H3 120.4 . . ? C3 C54 C55 119.5(3) . . ? C3 C54 H54 120.2 . . ? C55 C54 H54 120.2 . . ? N51 C55 C54 121.2(3) . . ? N51 C55 C6 114.4(3) . . ? C54 C55 C6 124.4(3) . . ? N2 C6 C7 121.7(3) . . ? N2 C6 C55 114.3(3) . . ? C7 C6 C55 123.9(3) . . ? C6 C7 C8 119.9(3) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C9 C8 C7 118.3(3) . . ? C9 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? C10 C9 C8 119.0(3) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? N2 C10 C9 123.5(3) . . ? N2 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 N2 C6 117.5(3) . . ? C10 N2 Mn1 126.7(2) . . ? C6 N2 Mn1 115.8(2) . . ? O1 C11 Mn1 174.7(3) . . ? O2 C12 Mn1 175.9(3) . . ? O3 C13 Mn1 177.1(3) . . ? C2 N1 C5 112.6(3) . . ? C2 N1 Mn1 129.5(2) . . ? C5 N1 Mn1 117.7(2) . . ? C4 C5 N1 115.6(3) . . ? C4 C5 H5 122.2 . . ? N1 C5 H5 122.2 . . ? C5 C4 S3 109.2(2) . . ? C5 C4 H4 125.4 . . ? S3 C4 H4 125.4 . . ? C4 S3 C2 92.39(15) . . ? N1 C2 S3 110.2(2) . . ? N1 C2 Au1 132.9(2) . . ? S3 C2 Au1 116.91(17) . . ? C2 Au1 P1 173.44(9) . . ? C23 P1 C29 103.77(15) . . ? C23 P1 C17 105.50(14) . . ? C29 P1 C17 107.70(15) . . ? C23 P1 Au1 117.04(11) . . ? C29 P1 Au1 109.96(10) . . ? C17 P1 Au1 112.19(11) . . ? C22 C17 C18 118.6(3) . . ? C22 C17 P1 119.0(2) . . ? C18 C17 P1 122.3(3) . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C17 120.8(3) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C28 C23 C24 119.3(3) . . ? C28 C23 P1 119.8(3) . . ? C24 C23 P1 120.8(2) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.2(4) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 119.9(3) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.2(4) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C23 120.2(4) . . ? C27 C28 H28 119.9 . . ? C23 C28 H28 119.9 . . ? C30 C29 C34 119.7(3) . . ? C30 C29 P1 123.4(3) . . ? C34 C29 P1 116.8(2) . . ? C31 C30 C29 119.4(3) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C32 C31 C30 120.2(3) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C31 C32 C33 120.7(3) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 119.3(3) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C29 120.7(3) . . ? C33 C34 H34 119.7 . . ? C29 C34 H34 119.7 . . ? F5 P2 F4 91.17(15) . . ? F5 P2 F6 90.01(13) . . ? F4 P2 F6 178.67(14) . . ? F5 P2 F1 90.16(13) . . ? F4 P2 F1 90.26(13) . . ? F6 P2 F1 89.13(12) . . ? F5 P2 F2 90.16(12) . . ? F4 P2 F2 89.64(12) . . ? F6 P2 F2 90.97(12) . . ? F1 P2 F2 179.67(14) . . ? F5 P2 F3 178.42(15) . . ? F4 P2 F3 90.35(15) . . ? F6 P2 F3 88.48(13) . . ? F1 P2 F3 90.28(14) . . ? F2 P2 F3 89.41(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 Mn1 N51 C1 -7.6(3) . . . . ? C11 Mn1 N51 C1 85.3(3) . . . . ? N2 Mn1 N51 C1 175.5(2) . . . . ? N1 Mn1 N51 C1 -98.2(2) . . . . ? C13 Mn1 N51 C55 167.0(2) . . . . ? C11 Mn1 N51 C55 -100.2(2) . . . . ? N2 Mn1 N51 C55 -9.89(19) . . . . ? N1 Mn1 N51 C55 76.4(2) . . . . ? C55 N51 C1 C52 -2.4(4) . . . . ? Mn1 N51 C1 C52 172.0(2) . . . . ? N51 C1 C52 C3 -0.7(4) . . . . ? C1 C52 C3 C54 3.0(4) . . . . ? C52 C3 C54 C55 -2.1(4) . . . . ? C1 N51 C55 C54 3.3(4) . . . . ? Mn1 N51 C55 C54 -171.7(2) . . . . ? C1 N51 C55 C6 -174.3(2) . . . . ? Mn1 N51 C55 C6 10.7(3) . . . . ? C3 C54 C55 N51 -1.1(4) . . . . ? C3 C54 C55 C6 176.3(3) . . . . ? N51 C55 C6 N2 -4.5(4) . . . . ? C54 C55 C6 N2 178.1(3) . . . . ? N51 C55 C6 C7 172.1(3) . . . . ? C54 C55 C6 C7 -5.3(5) . . . . ? N2 C6 C7 C8 1.0(4) . . . . ? C55 C6 C7 C8 -175.3(3) . . . . ? C6 C7 C8 C9 -1.1(4) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 N2 1.7(5) . . . . ? C9 C10 N2 C6 -1.8(4) . . . . ? C9 C10 N2 Mn1 179.3(2) . . . . ? C7 C6 N2 C10 0.4(4) . . . . ? C55 C6 N2 C10 177.1(2) . . . . ? C7 C6 N2 Mn1 179.4(2) . . . . ? C55 C6 N2 Mn1 -3.9(3) . . . . ? C12 Mn1 N2 C10 7.5(3) . . . . ? C11 Mn1 N2 C10 -79.6(3) . . . . ? N51 Mn1 N2 C10 -173.7(2) . . . . ? N1 Mn1 N2 C10 97.4(2) . . . . ? C12 Mn1 N2 C6 -171.4(2) . . . . ? C11 Mn1 N2 C6 101.5(2) . . . . ? N51 Mn1 N2 C6 7.33(19) . . . . ? N1 Mn1 N2 C6 -81.5(2) . . . . ? C13 Mn1 N1 C2 -43.1(3) . . . . ? C12 Mn1 N1 C2 -130.1(3) . . . . ? N2 Mn1 N1 C2 131.4(3) . . . . ? N51 Mn1 N1 C2 52.6(3) . . . . ? C13 Mn1 N1 C5 130.9(2) . . . . ? C12 Mn1 N1 C5 43.9(2) . . . . ? N2 Mn1 N1 C5 -54.5(2) . . . . ? N51 Mn1 N1 C5 -133.3(2) . . . . ? C2 N1 C5 C4 -0.8(4) . . . . ? Mn1 N1 C5 C4 -175.8(2) . . . . ? N1 C5 C4 S3 0.3(4) . . . . ? C5 C4 S3 C2 0.3(3) . . . . ? C5 N1 C2 S3 1.0(3) . . . . ? Mn1 N1 C2 S3 175.26(15) . . . . ? C5 N1 C2 Au1 -176.1(2) . . . . ? Mn1 N1 C2 Au1 -1.8(5) . . . . ? C4 S3 C2 N1 -0.7(3) . . . . ? C4 S3 C2 Au1 176.87(19) . . . . ? C23 P1 C17 C22 -172.3(3) . . . . ? C29 P1 C17 C22 77.3(3) . . . . ? Au1 P1 C17 C22 -43.8(3) . . . . ? C23 P1 C17 C18 3.1(3) . . . . ? C29 P1 C17 C18 -107.2(3) . . . . ? Au1 P1 C17 C18 131.6(2) . . . . ? C22 C17 C18 C19 0.8(5) . . . . ? P1 C17 C18 C19 -174.6(3) . . . . ? C17 C18 C19 C20 0.6(5) . . . . ? C18 C19 C20 C21 -2.0(5) . . . . ? C19 C20 C21 C22 1.9(5) . . . . ? C20 C21 C22 C17 -0.5(5) . . . . ? C18 C17 C22 C21 -0.9(5) . . . . ? P1 C17 C22 C21 174.7(2) . . . . ? C29 P1 C23 C28 -143.2(3) . . . . ? C17 P1 C23 C28 103.7(3) . . . . ? Au1 P1 C23 C28 -21.9(3) . . . . ? C29 P1 C23 C24 38.9(3) . . . . ? C17 P1 C23 C24 -74.2(3) . . . . ? Au1 P1 C23 C24 160.2(2) . . . . ? C28 C23 C24 C25 -0.5(5) . . . . ? P1 C23 C24 C25 177.4(3) . . . . ? C23 C24 C25 C26 0.6(5) . . . . ? C24 C25 C26 C27 -0.7(5) . . . . ? C25 C26 C27 C28 0.6(5) . . . . ? C26 C27 C28 C23 -0.4(5) . . . . ? C24 C23 C28 C27 0.4(5) . . . . ? P1 C23 C28 C27 -177.5(3) . . . . ? C23 P1 C29 C30 -120.1(3) . . . . ? C17 P1 C29 C30 -8.6(3) . . . . ? Au1 P1 C29 C30 113.9(3) . . . . ? C23 P1 C29 C34 60.5(3) . . . . ? C17 P1 C29 C34 172.0(3) . . . . ? Au1 P1 C29 C34 -65.4(3) . . . . ? C34 C29 C30 C31 0.7(5) . . . . ? P1 C29 C30 C31 -178.7(3) . . . . ? C29 C30 C31 C32 -1.0(5) . . . . ? C30 C31 C32 C33 0.8(6) . . . . ? C31 C32 C33 C34 -0.3(6) . . . . ? C32 C33 C34 C29 0.0(5) . . . . ? C30 C29 C34 C33 -0.2(5) . . . . ? P1 C29 C34 C33 179.2(3) . . . . ? #===END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-28 at 11:41:58 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : e:\xprogs\wingx\files\archive.dat # CIF files read : jv05bk2n struct data_8b _database_code_depnum_ccdc_archive 'CCDC 716676' _audit_creation_date 2008-04-28T11:41:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H18 Au N P S, Cl O4' _chemical_formula_sum 'C21 H18 Au Cl N O4 P S' _chemical_formula_weight 643.81 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 9.7030(3) _cell_length_b 16.6091(6) _cell_length_c 13.9180(4) _cell_angle_alpha 90 _cell_angle_beta 101.338(2) _cell_angle_gamma 90 _cell_volume 2199.22(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1881 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 22.53 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.944 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 7.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.4510 _exptl_absorpt_correction_T_max 0.7533 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_number 57620 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 27.88 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5245 _reflns_number_gt 4051 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'DIRDIF-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0206P)^2^+7.1515P] 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_number_reflns 5245 _refine_ls_number_parameters 302 _refine_ls_number_restraints 23 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0658 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.452 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.15 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2 C -0.0884(7) 0.0883(6) 0.0513(6) 0.0234(16) Uani 0.773(5) 1 d PD A 1 S3 S -0.0763(2) 0.15650(13) -0.03904(14) 0.0375(6) Uani 0.773(5) 1 d PD A 1 C4 C -0.2460(14) 0.1381(10) -0.0976(10) 0.053(4) Uani 0.773(5) 1 d PD A 1 H4 H -0.2906 0.1638 -0.1546 0.063 Uiso 0.773(5) 1 calc PR A 1 C5 C -0.3060(8) 0.0814(5) -0.0500(6) 0.045(2) Uani 0.773(5) 1 d PD A 1 H5 H -0.3975 0.0625 -0.0698 0.054 Uiso 0.773(5) 1 calc PR A 1 N1 N -0.214(2) 0.0554(18) 0.031(2) 0.056(4) Uani 0.773(5) 1 d PD A 1 H1 H -0.2373 0.0186 0.0684 0.067 Uiso 0.773(5) 1 calc PR A 1 Au1 Au 0.067655(19) 0.066744(11) 0.168912(13) 0.02331(6) Uani 1 1 d . . . P1 P 0.23875(13) 0.04624(7) 0.30471(8) 0.0199(3) Uani 1 1 d . A . C94 C 0.1949(5) 0.0853(3) 0.4164(3) 0.0225(10) Uani 1 1 d . . . C95 C 0.2377(5) 0.0463(3) 0.5058(3) 0.0270(11) Uani 1 1 d . A . H95 H 0.2828 -0.0033 0.5084 0.032 Uiso 1 1 calc R . . C6 C 0.2129(5) 0.0817(3) 0.5911(4) 0.0293(12) Uani 1 1 d . . . H6 H 0.2414 0.0558 0.6509 0.035 Uiso 1 1 calc R A . C7 C 0.1461(5) 0.1551(3) 0.5873(4) 0.0321(12) Uani 1 1 d . A . H7 H 0.1323 0.1794 0.6449 0.039 Uiso 1 1 calc R . . C8 C 0.0995(6) 0.1930(3) 0.4984(4) 0.0371(13) Uani 1 1 d . . . H8 H 0.0524 0.2419 0.4959 0.045 Uiso 1 1 calc R A . C9 C 0.1234(5) 0.1575(3) 0.4130(4) 0.0291(11) Uani 1 1 d . A . H9 H 0.091 0.1824 0.353 0.035 Uiso 1 1 calc R . . C10 C 0.4036(5) 0.0933(3) 0.2943(3) 0.0215(10) Uani 1 1 d . . . C11 C 0.4984(5) 0.1213(3) 0.3754(3) 0.0286(11) Uani 1 1 d . A . H11 H 0.4765 0.1177 0.4373 0.034 Uiso 1 1 calc R . . C12 C 0.6261(5) 0.1547(3) 0.3646(4) 0.0354(13) Uani 1 1 d . . . H12 H 0.689 0.1737 0.4191 0.042 Uiso 1 1 calc R A . C13 C 0.6589(6) 0.1594(3) 0.2724(4) 0.0370(13) Uani 1 1 d . A . H13 H 0.7445 0.1814 0.2652 0.044 Uiso 1 1 calc R . . C14 C 0.5662(5) 0.1319(3) 0.1914(4) 0.0335(12) Uani 1 1 d . . . H14 H 0.5892 0.1351 0.1297 0.04 Uiso 1 1 calc R A . C15 C 0.4384(5) 0.0995(3) 0.2019(4) 0.0287(11) Uani 1 1 d . A . H15 H 0.3752 0.0817 0.1469 0.034 Uiso 1 1 calc R . . C16 C 0.2758(5) -0.0598(3) 0.3274(3) 0.0223(10) Uani 1 1 d D . . C17 C 0.1610(14) -0.1094(10) 0.3272(9) 0.044(3) Uani 0.773(5) 1 d PD A 1 H17 H 0.0707 -0.0881 0.3178 0.053 Uiso 0.773(5) 1 calc PR A 1 C18 C 0.1832(15) -0.1909(10) 0.3412(11) 0.049(4) Uani 0.773(5) 1 d PD A 1 H18 H 0.1071 -0.2248 0.342 0.059 Uiso 0.773(5) 1 calc PR A 1 C19 C 0.3165(14) -0.2228(10) 0.3542(11) 0.030(3) Uani 0.773(5) 1 d PD A 1 H19 H 0.3293 -0.278 0.3633 0.036 Uiso 0.773(5) 1 calc PR A 1 C17B C 0.175(5) -0.112(3) 0.348(3) 0.044(3) Uani 0.227(5) 1 d PD A 2 H17B H 0.085 -0.0919 0.3452 0.053 Uiso 0.227(5) 1 calc PR A 2 C18B C 0.196(5) -0.193(4) 0.371(5) 0.049(4) Uani 0.227(5) 1 d PD A 2 H18B H 0.123 -0.2244 0.3854 0.059 Uiso 0.227(5) 1 calc PR A 2 C19B C 0.327(5) -0.226(4) 0.373(5) 0.030(3) Uani 0.227(5) 1 d PD A 2 H19B H 0.345 -0.2801 0.386 0.036 Uiso 0.227(5) 1 calc PR A 2 C20 C 0.4308(5) -0.1740(3) 0.3538(3) 0.0249(11) Uani 1 1 d D . . H20 H 0.5209 -0.1957 0.3639 0.03 Uiso 1 1 calc R A 1 C21 C 0.4099(5) -0.0921(3) 0.3381(3) 0.0235(10) Uani 1 1 d D A . H21 H 0.4858 -0.0587 0.3348 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.30954(16) 0.13092(9) 0.87787(11) 0.0429(3) Uani 1 1 d D . . O1 O 0.3031(5) 0.1601(4) 0.9707(3) 0.0741(16) Uani 1 1 d . A . O2 O 0.3922(4) 0.1824(3) 0.8292(3) 0.0463(11) Uani 1 1 d . A . O3 O 0.1621(6) 0.1325(5) 0.8222(4) 0.064(2) Uani 0.773(5) 1 d P A 1 O4 O 0.3545(7) 0.0510(3) 0.8648(7) 0.083(3) Uani 0.773(5) 1 d P A 1 O3B O 0.2101(19) 0.0790(15) 0.8389(15) 0.064(2) Uani 0.227(5) 1 d PD A 2 O4B O 0.423(2) 0.0743(11) 0.939(2) 0.083(3) Uani 0.227(5) 1 d PD A 2 C2B C -0.052(2) 0.096(3) 0.039(2) 0.0234(16) Uani 0.227(5) 1 d PD A 2 S3B S -0.224(2) 0.074(2) 0.017(2) 0.056(4) Uani 0.227(5) 1 d PD A 2 C4B C -0.254(3) 0.123(4) -0.093(3) 0.045(2) Uani 0.227(5) 1 d PD A 2 H4B H -0.3415 0.1273 -0.135 0.054 Uiso 0.227(5) 1 calc PR A 2 C5B C -0.132(3) 0.1538(15) -0.1102(16) 0.053(4) Uani 0.227(5) 1 d PD A 2 H5B H -0.1239 0.1794 -0.1682 0.063 Uiso 0.227(5) 1 calc PR A 2 N1B N -0.024(3) 0.1433(17) -0.0331(17) 0.0375(6) Uani 0.227(5) 1 d PD A 2 H1B H 0.0568 0.1654 -0.0306 0.045 Uiso 0.227(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.017(4) 0.027(4) 0.026(3) -0.009(3) 0.003(3) 0.002(4) S3 0.0523(15) 0.0368(12) 0.0190(9) 0.0007(7) -0.0033(10) 0.0154(10) C4 0.065(6) 0.058(9) 0.024(4) -0.020(4) -0.018(4) 0.036(6) C5 0.028(4) 0.054(6) 0.043(5) -0.027(4) -0.016(3) 0.022(4) N1 0.033(3) 0.073(12) 0.057(7) -0.028(6) -0.002(4) 0.002(5) Au1 0.02414(10) 0.02338(10) 0.01975(9) -0.00184(8) -0.00218(6) -0.00046(9) P1 0.0219(6) 0.0190(6) 0.0181(6) -0.0013(5) 0.0022(5) -0.0004(5) C94 0.024(2) 0.022(3) 0.023(2) -0.0040(19) 0.0068(19) -0.0031(19) C95 0.025(2) 0.033(3) 0.023(2) 0.001(2) 0.005(2) 0.007(2) C6 0.023(2) 0.043(3) 0.023(2) -0.001(2) 0.005(2) 0.002(2) C7 0.028(3) 0.040(3) 0.032(3) -0.011(2) 0.012(2) -0.002(2) C8 0.048(3) 0.026(3) 0.041(3) -0.004(2) 0.018(3) 0.006(3) C9 0.036(3) 0.021(3) 0.031(3) -0.001(2) 0.007(2) 0.007(2) C10 0.022(2) 0.019(2) 0.021(2) 0.0044(19) -0.0019(18) 0.0019(19) C11 0.031(3) 0.035(3) 0.019(2) 0.000(2) 0.000(2) -0.004(2) C12 0.027(3) 0.035(3) 0.040(3) 0.005(3) -0.002(2) -0.009(2) C13 0.027(3) 0.030(3) 0.056(4) 0.012(3) 0.012(3) 0.000(2) C14 0.033(3) 0.033(3) 0.037(3) 0.004(2) 0.015(3) 0.001(2) C15 0.037(3) 0.025(3) 0.024(3) 0.002(2) 0.004(2) 0.004(2) C16 0.019(2) 0.020(2) 0.027(2) -0.006(2) 0.0027(18) 0.0005(19) C17 0.017(4) 0.021(3) 0.095(8) 0.005(5) 0.011(5) 0.004(3) C18 0.025(4) 0.025(3) 0.099(12) 0.013(7) 0.016(6) -0.003(3) C19 0.031(4) 0.019(3) 0.039(8) 0.001(4) 0.001(4) 0.005(3) C17B 0.017(4) 0.021(3) 0.095(8) 0.005(5) 0.011(5) 0.004(3) C18B 0.025(4) 0.025(3) 0.099(12) 0.013(7) 0.016(6) -0.003(3) C19B 0.031(4) 0.019(3) 0.039(8) 0.001(4) 0.001(4) 0.005(3) C20 0.027(2) 0.028(3) 0.018(2) 0.0009(19) 0.001(2) 0.006(2) C21 0.017(2) 0.029(3) 0.021(2) 0.003(2) -0.0014(19) 0.0017(19) Cl1 0.0470(8) 0.0349(8) 0.0504(9) -0.0086(7) 0.0186(7) 0.0063(7) O1 0.080(4) 0.120(5) 0.021(2) -0.017(3) 0.006(2) -0.029(3) O2 0.033(2) 0.067(3) 0.040(2) 0.005(2) 0.0111(18) -0.002(2) O3 0.022(3) 0.128(7) 0.038(3) -0.017(4) -0.004(2) -0.009(3) O4 0.050(4) 0.028(3) 0.172(8) -0.024(4) 0.025(4) 0.000(3) O3B 0.022(3) 0.128(7) 0.038(3) -0.017(4) -0.004(2) -0.009(3) O4B 0.050(4) 0.028(3) 0.172(8) -0.024(4) 0.025(4) 0.000(3) C2B 0.017(4) 0.027(4) 0.026(3) -0.009(3) 0.003(3) 0.002(4) S3B 0.033(3) 0.073(12) 0.057(7) -0.028(6) -0.002(4) 0.002(5) C4B 0.028(4) 0.054(6) 0.043(5) -0.027(4) -0.016(3) 0.022(4) C5B 0.065(6) 0.058(9) 0.024(4) -0.020(4) -0.018(4) 0.036(6) N1B 0.0523(15) 0.0368(12) 0.0190(9) 0.0007(7) -0.0033(10) 0.0154(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 N1 1.312(19) . ? C2 S3 1.714(8) . ? C2 Au1 2.031(7) . ? S3 C4 1.715(11) . ? C4 C5 1.348(17) . ? C4 H4 0.93 . ? C5 N1 1.37(2) . ? C5 H5 0.93 . ? N1 H1 0.86 . ? Au1 C2B 2.01(2) . ? Au1 P1 2.2827(12) . ? P1 C94 1.811(5) . ? P1 C10 1.812(5) . ? P1 C16 1.813(5) . ? C94 C9 1.381(7) . ? C94 C95 1.392(7) . ? C95 C6 1.387(7) . ? C95 H95 0.93 . ? C6 C7 1.378(7) . ? C6 H6 0.93 . ? C7 C8 1.382(7) . ? C7 H7 0.93 . ? C8 C9 1.387(7) . ? C8 H8 0.93 . ? C9 H9 0.93 . ? C10 C11 1.388(6) . ? C10 C15 1.395(6) . ? C11 C12 1.392(7) . ? C11 H11 0.93 . ? C12 C13 1.384(8) . ? C12 H12 0.93 . ? C13 C14 1.375(8) . ? C13 H13 0.93 . ? C14 C15 1.386(7) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C16 C17B 1.38(2) . ? C16 C17 1.385(10) . ? C16 C21 1.388(6) . ? C17 C18 1.380(9) . ? C17 H17 0.93 . ? C18 C19 1.376(9) . ? C18 H18 0.93 . ? C19 C20 1.374(11) . ? C19 H19 0.93 . ? C17B C18B 1.382(18) . ? C17B H17B 0.93 . ? C18B C19B 1.382(18) . ? C18B H18B 0.93 . ? C19B C20 1.39(2) . ? C19B H19B 0.93 . ? C20 C21 1.387(7) . ? C20 H20 0.93 . ? C21 H21 0.93 . ? Cl1 O3B 1.329(15) . ? Cl1 O1 1.392(4) . ? Cl1 O4 1.420(6) . ? Cl1 O2 1.431(4) . ? Cl1 O3 1.488(5) . ? Cl1 O4B 1.562(16) . ? C2B N1B 1.34(2) . ? C2B S3B 1.679(19) . ? S3B C4B 1.72(2) . ? C4B C5B 1.35(3) . ? C4B H4B 0.93 . ? C5B N1B 1.36(2) . ? C5B H5B 0.93 . ? N1B H1B 0.86 . ? 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 C2 S3 108.3(10) . . ? N1 C2 Au1 127.6(11) . . ? S3 C2 Au1 124.1(4) . . ? C2 S3 C4 91.9(5) . . ? C5 C4 S3 111.0(6) . . ? C5 C4 H4 124.5 . . ? S3 C4 H4 124.5 . . ? C4 C5 N1 110.5(11) . . ? C4 C5 H5 124.7 . . ? N1 C5 H5 124.7 . . ? C2 N1 C5 118.2(17) . . ? C2 N1 H1 120.9 . . ? C5 N1 H1 120.9 . . ? C2B Au1 C2 12.7(6) . . ? C2B Au1 P1 168.3(6) . . ? C2 Au1 P1 177.6(3) . . ? C94 P1 C10 105.9(2) . . ? C94 P1 C16 105.7(2) . . ? C10 P1 C16 106.6(2) . . ? C94 P1 Au1 113.71(16) . . ? C10 P1 Au1 112.27(15) . . ? C16 P1 Au1 112.08(15) . . ? C9 C94 C95 119.7(4) . . ? C9 C94 P1 118.8(4) . . ? C95 C94 P1 121.4(4) . . ? C6 C95 C94 119.7(5) . . ? C6 C95 H95 120.1 . . ? C94 C95 H95 120.1 . . ? C7 C6 C95 120.2(5) . . ? C7 C6 H6 119.9 . . ? C95 C6 H6 119.9 . . ? C6 C7 C8 120.4(5) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C94 C9 C8 120.4(5) . . ? C94 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C15 118.9(4) . . ? C11 C10 P1 122.2(4) . . ? C15 C10 P1 118.9(4) . . ? C10 C11 C12 120.5(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.6(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.9(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 120.6(5) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C17B C16 C21 115(3) . . ? C17 C16 C21 120.5(9) . . ? C17B C16 P1 122(3) . . ? C17 C16 P1 116.5(8) . . ? C21 C16 P1 122.9(4) . . ? C18 C17 C16 118.7(11) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C19 C18 C17 120.9(9) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C20 C19 C18 120.7(11) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C18B C17B C16 126(4) . . ? C18B C17B H17B 117.2 . . ? C16 C17B H17B 117.2 . . ? C17B C18B C19B 119(3) . . ? C17B C18B H18B 120.7 . . ? C19B C18B H18B 120.7 . . ? C18B C19B C20 117(4) . . ? C18B C19B H19B 121.6 . . ? C20 C19B H19B 121.6 . . ? C19 C20 C21 119.1(9) . . ? C21 C20 C19B 123(3) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C19B C20 H20 115.3 . . ? C20 C21 C16 120.1(4) . . ? C20 C21 H21 120 . . ? C16 C21 H21 120 . . ? O3B Cl1 O1 116.3(10) . . ? O3B Cl1 O4 63.7(11) . . ? O1 Cl1 O4 121.0(5) . . ? O3B Cl1 O2 128.6(10) . . ? O1 Cl1 O2 111.3(3) . . ? O4 Cl1 O2 106.4(4) . . ? O1 Cl1 O3 105.3(3) . . ? O4 Cl1 O3 103.7(4) . . ? O2 Cl1 O3 108.3(3) . . ? O3B Cl1 O4B 102.0(14) . . ? O1 Cl1 O4B 81.9(10) . . ? O4 Cl1 O4B 46.1(9) . . ? O2 Cl1 O4B 102.6(9) . . ? O3 Cl1 O4B 142.6(9) . . ? N1B C2B S3B 109.8(15) . . ? N1B C2B Au1 130.7(18) . . ? S3B C2B Au1 118.7(13) . . ? C2B S3B C4B 92.5(14) . . ? C5B C4B S3B 109.5(15) . . ? C5B C4B H4B 125.2 . . ? S3B C4B H4B 125.2 . . ? C4B C5B N1B 112.4(19) . . ? C4B C5B H5B 123.8 . . ? N1B C5B H5B 123.8 . . ? C2B N1B C5B 115(2) . . ? C2B N1B H1B 122.4 . . ? C5B N1B H1B 122.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 S3 C4 1.5(18) . . . . ? Au1 C2 S3 C4 -177.3(9) . . . . ? C2 S3 C4 C5 -1.0(12) . . . . ? S3 C4 C5 N1 0(2) . . . . ? S3 C2 N1 C5 -2(3) . . . . ? Au1 C2 N1 C5 177.0(14) . . . . ? C4 C5 N1 C2 1(3) . . . . ? N1 C2 Au1 C2B 157(8) . . . . ? S3 C2 Au1 C2B -24(7) . . . . ? C2B Au1 P1 C94 123(6) . . . . ? C2B Au1 P1 C10 3(6) . . . . ? C2B Au1 P1 C16 -117(6) . . . . ? C10 P1 C94 C9 85.6(4) . . . . ? C16 P1 C94 C9 -161.5(4) . . . . ? Au1 P1 C94 C9 -38.1(4) . . . . ? C10 P1 C94 C95 -91.2(4) . . . . ? C16 P1 C94 C95 21.7(5) . . . . ? Au1 P1 C94 C95 145.1(4) . . . . ? C9 C94 C95 C6 -2.4(7) . . . . ? P1 C94 C95 C6 174.3(4) . . . . ? C94 C95 C6 C7 0.0(7) . . . . ? C95 C6 C7 C8 2.0(8) . . . . ? C6 C7 C8 C9 -1.5(8) . . . . ? C95 C94 C9 C8 2.9(8) . . . . ? P1 C94 C9 C8 -174.0(4) . . . . ? C7 C8 C9 C94 -0.9(8) . . . . ? C94 P1 C10 C11 25.5(5) . . . . ? C16 P1 C10 C11 -86.8(4) . . . . ? Au1 P1 C10 C11 150.1(4) . . . . ? C94 P1 C10 C15 -156.5(4) . . . . ? C16 P1 C10 C15 91.3(4) . . . . ? Au1 P1 C10 C15 -31.8(4) . . . . ? C15 C10 C11 C12 -0.2(7) . . . . ? P1 C10 C11 C12 177.9(4) . . . . ? C10 C11 C12 C13 -0.5(8) . . . . ? C11 C12 C13 C14 0.4(8) . . . . ? C12 C13 C14 C15 0.3(8) . . . . ? C13 C14 C15 C10 -1.0(8) . . . . ? C11 C10 C15 C14 0.9(7) . . . . ? P1 C10 C15 C14 -177.2(4) . . . . ? C94 P1 C16 C17B 62(2) . . . . ? C10 P1 C16 C17B 174(2) . . . . ? Au1 P1 C16 C17B -62(2) . . . . ? C94 P1 C16 C17 74.5(7) . . . . ? C10 P1 C16 C17 -173.1(7) . . . . ? Au1 P1 C16 C17 -49.9(7) . . . . ? C94 P1 C16 C21 -109.7(4) . . . . ? C10 P1 C16 C21 2.7(4) . . . . ? Au1 P1 C16 C21 125.9(4) . . . . ? C17B C16 C17 C18 -63(18) . . . . ? C21 C16 C17 C18 2.2(10) . . . . ? P1 C16 C17 C18 178.1(6) . . . . ? C16 C17 C18 C19 -0.7(12) . . . . ? C17 C18 C19 C20 0.2(16) . . . . ? C17 C16 C17B C18B 116(18) . . . . ? C21 C16 C17B C18B -3.9(18) . . . . ? P1 C16 C17B C18B -176.2(14) . . . . ? C16 C17B C18B C19B -2(3) . . . . ? C17B C18B C19B C20 2(5) . . . . ? C18 C19 C20 C21 -1.3(15) . . . . ? C18 C19 C20 C19B 11E1(2) . . . . ? C18B C19B C20 C19 -7E1(2) . . . . ? C18B C19B C20 C21 3(6) . . . . ? C19 C20 C21 C16 2.8(10) . . . . ? C19B C20 C21 C16 -9(3) . . . . ? C17B C16 C21 C20 9(2) . . . . ? C17 C16 C21 C20 -3.3(9) . . . . ? P1 C16 C21 C20 -179.0(3) . . . . ? C2 Au1 C2B N1B 161(11) . . . . ? P1 Au1 C2B N1B -8(10) . . . . ? C2 Au1 C2B S3B -7(5) . . . . ? P1 Au1 C2B S3B -177(4) . . . . ? N1B C2B S3B C4B 4(4) . . . . ? Au1 C2B S3B C4B 174(4) . . . . ? C2B S3B C4B C5B 1(5) . . . . ? S3B C4B C5B N1B -5(6) . . . . ? S3B C2B N1B C5B -8(4) . . . . ? Au1 C2B N1B C5B -177(3) . . . . ? C4B C5B N1B C2B 8(5) . . . . ?