# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Takumi Konno' _publ_contact_author_address ; Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka 560-0043, JAPAN ; _publ_contact_author_email konno@chem.sci.osaka-u.ac.jp _publ_contact_author_fax ' 81-6-6850-5765 ' _publ_contact_author_phone ' 81-6-6850-5765 ' # TITLE AND AUTHOR LIST _publ_section_title ;A bis-bipyridine osmium(II) complex with an N,S-chelating 2-aminoethanesulfinate: photoinduced conversion of amine to imine donor group by air oxidation ; loop_ _publ_author_name 'Motoshi Tamura' 'Kiyoshi Tsuge' 'Asako Igashira-Kamiyama' 'Takumi Konno' data_1 _database_code_depnum_ccdc_archive 'CCDC 834770' #TrackingRef 'web_deposit_cif_file_0_AsakoIgashira_1310689294.konno.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Cl2 N5 Na O10 Os S' _chemical_formula_weight 832.60 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Os Os -1.2165 7.6030 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.5421(3) _cell_length_b 16.8001(7) _cell_length_c 34.0526(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.6130(10) _cell_angle_gamma 90.00 _cell_volume 5422.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 19644 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.51 _exptl_crystal_description platelet _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.040 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3248 _exptl_absorpt_coefficient_mu 5.059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.349 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26730 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6220 _reflns_number_gt 5150 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'Crystal Structure' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0547P)^2^+44.8078P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6220 _refine_ls_number_parameters 379 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.096 _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 Os1 Os 0.27018(3) 0.471084(14) 0.118883(7) 0.03067(10) Uani 1 1 d . . . S1 S 0.45253(19) 0.47616(10) 0.16691(5) 0.0387(4) Uani 1 1 d . . . O1 O 0.4422(7) 0.4228(4) 0.20094(17) 0.0652(17) Uani 1 1 d . . . O2 O 0.5067(6) 0.5538(3) 0.18211(16) 0.0498(12) Uani 1 1 d . . . N1 N 0.4313(7) 0.4654(4) 0.07933(18) 0.0380(13) Uani 1 1 d . . . H1 H 0.422(8) 0.495(5) 0.058(3) 0.046 Uiso 1 1 d . . . H2 H 0.428(9) 0.426(5) 0.067(2) 0.046 Uiso 1 1 d . . . C1 C 0.5898(8) 0.4360(5) 0.1415(2) 0.0545(19) Uani 1 1 d . . . H3 H 0.6831 0.4489 0.1560 0.065 Uiso 1 1 calc R . . H4 H 0.5807 0.3774 0.1396 0.065 Uiso 1 1 calc R . . C2 C 0.5769(8) 0.4717(5) 0.1013(3) 0.054(2) Uani 1 1 d . . . H5 H 0.6445 0.4449 0.0856 0.065 Uiso 1 1 calc R . . H6 H 0.6037 0.5286 0.1036 0.065 Uiso 1 1 calc R . . N2 N 0.1204(6) 0.4705(3) 0.15817(15) 0.0326(11) Uani 1 1 d . . . C3 C 0.0564(8) 0.5358(4) 0.1713(2) 0.0432(16) Uani 1 1 d . . . H7 H 0.0839 0.5868 0.1630 0.052 Uiso 1 1 calc R . . C4 C -0.0441(8) 0.5310(4) 0.1956(2) 0.0454(17) Uani 1 1 d . . . H8 H -0.0859 0.5781 0.2044 0.054 Uiso 1 1 calc R . . C5 C -0.0870(8) 0.4576(5) 0.2080(2) 0.0467(17) Uani 1 1 d . . . H9 H -0.1590 0.4533 0.2250 0.056 Uiso 1 1 calc R . . C6 C -0.0227(7) 0.3907(5) 0.1951(2) 0.0428(16) Uani 1 1 d . . . H10 H -0.0502 0.3395 0.2032 0.051 Uiso 1 1 calc R . . C7 C 0.0825(7) 0.3977(4) 0.17024(19) 0.0374(14) Uani 1 1 d . . . C8 C 0.1596(7) 0.3303(4) 0.15549(19) 0.0344(13) Uani 1 1 d . . . C9 C 0.1367(8) 0.2521(4) 0.1657(2) 0.0411(15) Uani 1 1 d . . . H11 H 0.0692 0.2394 0.1832 0.049 Uiso 1 1 calc R . . C10 C 0.2128(8) 0.1931(4) 0.1502(2) 0.0494(18) Uani 1 1 d . . . H12 H 0.1992 0.1390 0.1570 0.059 Uiso 1 1 calc R . . C11 C 0.3086(9) 0.2126(4) 0.1248(2) 0.0494(18) Uani 1 1 d . . . H13 H 0.3620 0.1722 0.1139 0.059 Uiso 1 1 calc R . . C12 C 0.3272(8) 0.2911(4) 0.1153(2) 0.0452(17) Uani 1 1 d . . . H14 H 0.3930 0.3042 0.0974 0.054 Uiso 1 1 calc R . . N3 N 0.2546(6) 0.3504(3) 0.13071(15) 0.0335(11) Uani 1 1 d . . . N4 N 0.2461(6) 0.5895(3) 0.10316(17) 0.0369(12) Uani 1 1 d . . . C13 C 0.3325(8) 0.6500(4) 0.1160(2) 0.0429(16) Uani 1 1 d . . . H15 H 0.4132 0.6389 0.1342 0.051 Uiso 1 1 calc R . . C14 C 0.3080(9) 0.7276(4) 0.1035(3) 0.054(2) Uani 1 1 d . . . H16 H 0.3711 0.7686 0.1134 0.064 Uiso 1 1 calc R . . C15 C 0.1933(9) 0.7457(5) 0.0772(2) 0.0522(19) Uani 1 1 d . . . H17 H 0.1766 0.7987 0.0682 0.063 Uiso 1 1 calc R . . C16 C 0.1027(9) 0.6851(4) 0.0641(2) 0.0489(18) Uani 1 1 d . . . H18 H 0.0216 0.6960 0.0460 0.059 Uiso 1 1 calc R . . C17 C 0.1308(7) 0.6076(4) 0.07750(18) 0.0352(14) Uani 1 1 d . . . C18 C 0.0450(8) 0.5395(5) 0.0629(2) 0.0416(16) Uani 1 1 d . . . C19 C -0.0868(8) 0.5460(5) 0.0403(2) 0.0491(18) Uani 1 1 d . . . H19 H -0.1266 0.5969 0.0342 0.059 Uiso 1 1 calc R . . C20 C -0.1578(9) 0.4789(6) 0.0272(2) 0.057(2) Uani 1 1 d . . . H20 H -0.2481 0.4826 0.0123 0.069 Uiso 1 1 calc R . . C21 C -0.0966(8) 0.4053(6) 0.0358(2) 0.0513(19) Uani 1 1 d . . . H21 H -0.1413 0.3579 0.0255 0.062 Uiso 1 1 calc R . . C22 C 0.0307(8) 0.4018(5) 0.0596(2) 0.0442(16) Uani 1 1 d . . . H22 H 0.0710 0.3512 0.0662 0.053 Uiso 1 1 calc R . . N5 N 0.1002(6) 0.4678(3) 0.07379(15) 0.0330(12) Uani 1 1 d . . . Na1 Na 0.5000 0.3363(2) 0.2500 0.0468(9) Uani 1 2 d S . . Na2 Na 0.5000 0.5784(3) 0.2500 0.0590(11) Uani 1 2 d S . . O3 O 0.2631(8) 0.2871(4) 0.2518(2) 0.092(3) Uani 1 1 d D . . Cl1A Cl 0.2815(5) 0.2194(3) 0.27628(13) 0.0423(10) Uiso 0.50 1 d P . 1 O4A O 0.258(3) 0.1274(15) 0.2570(7) 0.116(8) Uiso 0.50 1 d P . 1 O5A O 0.4192(16) 0.2136(9) 0.2906(4) 0.083(4) Uiso 0.50 1 d P . 1 O6A O 0.1936(16) 0.2159(9) 0.3067(4) 0.076(4) Uiso 0.50 1 d P . 1 Cl1B Cl 0.2495(5) 0.2060(3) 0.26895(14) 0.0508(12) Uiso 0.50 1 d P . 2 O4B O 0.2455(18) 0.1513(8) 0.2487(4) 0.068(4) Uiso 0.50 1 d PD . 2 O5B O 0.3052(17) 0.2157(10) 0.3090(4) 0.098(5) Uiso 0.50 1 d PD . 2 O6B O 0.0936(15) 0.2092(11) 0.2685(5) 0.111(6) Uiso 0.50 1 d PD . 2 Cl2 Cl 0.0360(2) 0.15615(11) 0.01553(6) 0.0503(4) Uani 1 1 d . . . O7 O 0.1097(11) 0.1616(5) -0.0176(3) 0.116(3) Uani 1 1 d . A . O8A O 0.0176(14) 0.2389(8) 0.0267(4) 0.072(3) Uiso 0.50 1 d P A 1 O9A O 0.1139(17) 0.1175(11) 0.0487(5) 0.083(4) Uiso 0.50 1 d P A 1 O10A O -0.094(2) 0.1164(14) 0.0099(6) 0.121(6) Uiso 0.50 1 d P A 1 O8B O -0.1000(19) 0.1929(12) 0.0120(5) 0.100(5) Uiso 0.50 1 d P A 2 O9B O 0.124(2) 0.1713(13) 0.0499(5) 0.104(5) Uiso 0.50 1 d P A 2 O10B O 0.002(2) 0.0695(11) 0.0138(5) 0.102(5) Uiso 0.50 1 d P 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 Os1 0.03401(16) 0.02531(14) 0.03277(15) 0.00313(9) 0.00413(10) -0.00121(9) S1 0.0406(9) 0.0335(9) 0.0404(9) 0.0025(6) -0.0015(7) -0.0015(7) O1 0.069(4) 0.064(4) 0.058(3) 0.021(3) -0.015(3) -0.011(3) O2 0.057(3) 0.040(3) 0.050(3) -0.003(2) -0.005(2) -0.002(2) N1 0.042(3) 0.043(3) 0.031(3) 0.005(2) 0.012(3) 0.000(3) C1 0.046(4) 0.059(5) 0.057(5) -0.003(4) 0.003(4) 0.007(4) C2 0.032(4) 0.069(6) 0.067(5) 0.003(4) 0.031(4) 0.004(3) N2 0.042(3) 0.034(3) 0.020(2) 0.0002(19) 0.000(2) 0.002(2) C3 0.048(4) 0.034(4) 0.046(4) -0.002(3) 0.000(3) 0.005(3) C4 0.042(4) 0.047(4) 0.049(4) -0.004(3) 0.014(3) 0.003(3) C5 0.037(4) 0.066(5) 0.040(4) 0.001(3) 0.013(3) -0.001(3) C6 0.037(4) 0.048(4) 0.045(4) 0.003(3) 0.012(3) -0.007(3) C7 0.042(4) 0.032(3) 0.037(3) 0.001(2) 0.000(3) 0.001(3) C8 0.037(3) 0.028(3) 0.037(3) 0.003(2) 0.001(3) -0.008(3) C9 0.044(4) 0.032(3) 0.048(4) 0.010(3) 0.007(3) -0.005(3) C10 0.053(4) 0.027(3) 0.068(5) 0.008(3) 0.006(4) -0.005(3) C11 0.054(4) 0.030(4) 0.066(5) -0.007(3) 0.014(4) -0.001(3) C12 0.056(4) 0.030(4) 0.053(4) -0.002(3) 0.018(3) -0.001(3) N3 0.041(3) 0.029(3) 0.032(3) 0.000(2) 0.005(2) -0.003(2) N4 0.042(3) 0.030(3) 0.042(3) 0.001(2) 0.018(2) 0.004(2) C13 0.048(4) 0.033(4) 0.048(4) 0.006(3) 0.009(3) 0.001(3) C14 0.068(5) 0.030(4) 0.063(5) 0.010(3) 0.008(4) -0.002(4) C15 0.063(5) 0.033(4) 0.062(5) 0.016(3) 0.014(4) 0.008(3) C16 0.055(4) 0.041(4) 0.052(4) 0.012(3) 0.011(4) 0.012(3) C17 0.033(3) 0.046(4) 0.029(3) 0.005(3) 0.010(3) 0.005(3) C18 0.038(4) 0.052(4) 0.036(4) 0.001(3) 0.008(3) 0.005(3) C19 0.039(4) 0.066(5) 0.041(4) 0.011(3) -0.001(3) 0.008(4) C20 0.042(4) 0.090(7) 0.041(4) 0.007(4) 0.006(3) -0.004(4) C21 0.042(4) 0.073(6) 0.039(4) -0.002(4) 0.003(3) -0.018(4) C22 0.052(4) 0.045(4) 0.036(3) 0.002(3) 0.009(3) -0.007(3) N5 0.031(3) 0.044(3) 0.024(2) 0.001(2) 0.003(2) -0.005(2) Na1 0.049(2) 0.034(2) 0.056(2) 0.000 0.0007(19) 0.000 Na2 0.067(3) 0.064(3) 0.047(2) 0.000 0.010(2) 0.000 O3 0.090(6) 0.092(6) 0.091(5) 0.037(4) 0.003(4) -0.019(5) Cl2 0.0588(11) 0.0382(9) 0.0525(10) 0.0021(7) 0.0003(9) 0.0047(8) O7 0.180(10) 0.091(6) 0.089(6) -0.019(5) 0.068(6) -0.036(6) _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 Os1 N4 2.066(5) . ? Os1 N2 2.067(6) . ? Os1 N3 2.076(5) . ? Os1 N5 2.102(5) . ? Os1 N1 2.160(6) . ? Os1 S1 2.2481(18) . ? S1 O2 1.476(6) . ? S1 O1 1.477(6) . ? S1 C1 1.784(8) . ? S1 Na2 3.296(3) . ? O1 Na1 2.236(6) . ? O2 Na2 2.356(5) . ? N1 C2 1.503(11) . ? N1 H1 0.87(9) . ? N1 H2 0.79(8) . ? C1 C2 1.487(12) . ? C1 H3 0.9900 . ? C1 H4 0.9900 . ? C2 H5 0.9900 . ? C2 H6 0.9900 . ? N2 C7 1.352(8) . ? N2 C3 1.357(9) . ? C3 C4 1.339(11) . ? C3 H7 0.9500 . ? C4 C5 1.380(11) . ? C4 H8 0.9500 . ? C5 C6 1.377(11) . ? C5 H9 0.9500 . ? C6 C7 1.390(9) . ? C6 H10 0.9500 . ? C7 C8 1.471(9) . ? C8 N3 1.351(8) . ? C8 C9 1.382(9) . ? C9 C10 1.370(10) . ? C9 H11 0.9500 . ? C10 C11 1.367(11) . ? C10 H12 0.9500 . ? C11 C12 1.375(10) . ? C11 H13 0.9500 . ? C12 N3 1.353(9) . ? C12 H14 0.9500 . ? N4 C13 1.350(9) . ? N4 C17 1.359(9) . ? C13 C14 1.382(10) . ? C13 H15 0.9500 . ? C14 C15 1.366(12) . ? C14 H16 0.9500 . ? C15 C16 1.376(11) . ? C15 H17 0.9500 . ? C16 C17 1.397(10) . ? C16 H18 0.9500 . ? C17 C18 1.460(10) . ? C18 N5 1.349(9) . ? C18 C19 1.402(10) . ? C19 C20 1.364(12) . ? C19 H19 0.9500 . ? C20 C21 1.385(12) . ? C20 H20 0.9500 . ? C21 C22 1.382(11) . ? C21 H21 0.9500 . ? C22 N5 1.352(9) . ? C22 H22 0.9500 . ? Na1 O1 2.236(6) 2_655 ? Na1 O3 2.414(7) 2_655 ? Na1 O3 2.414(7) . ? Na1 O5A 2.645(16) 2_655 ? Na1 O5A 2.645(16) . ? Na1 Cl1A 3.072(5) . ? Na1 Cl1A 3.072(5) 2_655 ? Na1 Na2 4.067(6) . ? Na2 O2 2.356(5) 2_655 ? Na2 O6B 2.429(18) 3 ? Na2 O6B 2.429(18) 4 ? Na2 O4A 2.58(3) 3 ? Na2 O4A 2.58(3) 4 ? Na2 O4B 2.649(16) 4 ? Na2 O4B 2.649(16) 3 ? Na2 Cl1B 3.214(7) 3 ? Na2 Cl1B 3.214(6) 4 ? Na2 S1 3.296(3) 2_655 ? O3 Cl1A 1.410(7) . ? O3 Cl1B 1.494(8) . ? Cl1A O5A 1.352(16) . ? Cl1A O6A 1.408(15) . ? Cl1A O4A 1.68(3) . ? O4A Na2 2.58(3) 3_445 ? Cl1B O4B 1.147(13) . ? Cl1B O5B 1.416(13) . ? Cl1B O6B 1.487(15) . ? Cl1B Na2 3.214(6) 3_445 ? O4B Na2 2.649(16) 3_445 ? O6B Na2 2.429(18) 3_445 ? Cl2 O9B 1.380(19) . ? Cl2 O10A 1.40(2) . ? Cl2 O7 1.400(8) . ? Cl2 O8B 1.430(18) . ? Cl2 O9A 1.435(16) . ? Cl2 O8A 1.458(14) . ? Cl2 O10B 1.490(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Os1 N2 96.2(2) . . ? N4 Os1 N3 169.2(2) . . ? N2 Os1 N3 78.4(2) . . ? N4 Os1 N5 77.4(2) . . ? N2 Os1 N5 86.6(2) . . ? N3 Os1 N5 92.9(2) . . ? N4 Os1 N1 86.9(2) . . ? N2 Os1 N1 176.7(2) . . ? N3 Os1 N1 98.6(2) . . ? N5 Os1 N1 95.1(2) . . ? N4 Os1 S1 101.86(17) . . ? N2 Os1 S1 93.68(15) . . ? N3 Os1 S1 87.86(15) . . ? N5 Os1 S1 179.28(15) . . ? N1 Os1 S1 84.74(18) . . ? O2 S1 O1 108.3(3) . . ? O2 S1 C1 104.9(4) . . ? O1 S1 C1 105.7(4) . . ? O2 S1 Os1 120.0(2) . . ? O1 S1 Os1 115.6(2) . . ? C1 S1 Os1 100.5(3) . . ? O1 S1 Na2 70.0(3) . . ? C1 S1 Na2 125.3(3) . . ? Os1 S1 Na2 131.50(8) . . ? S1 O1 Na1 161.4(4) . . ? S1 O2 Na2 116.8(3) . . ? C2 N1 Os1 111.8(4) . . ? C2 N1 H1 112(5) . . ? Os1 N1 H1 119(6) . . ? C2 N1 H2 108(6) . . ? Os1 N1 H2 112(6) . . ? H1 N1 H2 92(8) . . ? C2 C1 S1 107.9(6) . . ? C2 C1 H3 110.1 . . ? S1 C1 H3 110.1 . . ? C2 C1 H4 110.1 . . ? S1 C1 H4 110.1 . . ? H3 C1 H4 108.4 . . ? C1 C2 N1 113.8(6) . . ? C1 C2 H5 108.8 . . ? N1 C2 H5 108.8 . . ? C1 C2 H6 108.8 . . ? N1 C2 H6 108.8 . . ? H5 C2 H6 107.7 . . ? C7 N2 C3 118.9(6) . . ? C7 N2 Os1 115.5(4) . . ? C3 N2 Os1 125.5(5) . . ? C4 C3 N2 122.5(7) . . ? C4 C3 H7 118.7 . . ? N2 C3 H7 118.7 . . ? C3 C4 C5 120.1(7) . . ? C3 C4 H8 120.0 . . ? C5 C4 H8 120.0 . . ? C6 C5 C4 118.2(7) . . ? C6 C5 H9 120.9 . . ? C4 C5 H9 120.9 . . ? C5 C6 C7 120.3(7) . . ? C5 C6 H10 119.8 . . ? C7 C6 H10 119.8 . . ? N2 C7 C6 120.0(6) . . ? N2 C7 C8 115.5(6) . . ? C6 C7 C8 124.5(6) . . ? N3 C8 C9 122.1(6) . . ? N3 C8 C7 114.7(5) . . ? C9 C8 C7 123.2(6) . . ? C10 C9 C8 119.0(7) . . ? C10 C9 H11 120.5 . . ? C8 C9 H11 120.5 . . ? C11 C10 C9 119.5(7) . . ? C11 C10 H12 120.3 . . ? C9 C10 H12 120.3 . . ? C10 C11 C12 119.6(7) . . ? C10 C11 H13 120.2 . . ? C12 C11 H13 120.2 . . ? N3 C12 C11 121.9(7) . . ? N3 C12 H14 119.1 . . ? C11 C12 H14 119.1 . . ? C8 N3 C12 118.0(6) . . ? C8 N3 Os1 115.7(4) . . ? C12 N3 Os1 126.3(5) . . ? C13 N4 C17 117.3(6) . . ? C13 N4 Os1 126.6(5) . . ? C17 N4 Os1 116.1(5) . . ? N4 C13 C14 122.4(7) . . ? N4 C13 H15 118.8 . . ? C14 C13 H15 118.8 . . ? C15 C14 C13 120.3(8) . . ? C15 C14 H16 119.8 . . ? C13 C14 H16 119.8 . . ? C14 C15 C16 118.4(7) . . ? C14 C15 H17 120.8 . . ? C16 C15 H17 120.8 . . ? C15 C16 C17 119.5(7) . . ? C15 C16 H18 120.2 . . ? C17 C16 H18 120.2 . . ? N4 C17 C16 122.0(7) . . ? N4 C17 C18 115.1(6) . . ? C16 C17 C18 122.7(6) . . ? N5 C18 C19 121.2(7) . . ? N5 C18 C17 114.8(6) . . ? C19 C18 C17 124.0(7) . . ? C20 C19 C18 119.8(8) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 119.1(8) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C22 C21 C20 118.9(8) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? N5 C22 C21 122.5(7) . . ? N5 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? C18 N5 C22 118.3(6) . . ? C18 N5 Os1 114.9(4) . . ? C22 N5 Os1 126.0(5) . . ? O1 Na1 O1 98.8(4) . 2_655 ? O1 Na1 O3 110.8(3) . 2_655 ? O1 Na1 O3 95.2(2) 2_655 2_655 ? O1 Na1 O3 95.2(2) . . ? O1 Na1 O3 110.8(3) 2_655 . ? O3 Na1 O3 140.0(4) 2_655 . ? O1 Na1 O5A 100.2(4) . 2_655 ? O1 Na1 O5A 146.7(4) 2_655 2_655 ? O3 Na1 O5A 52.4(4) 2_655 2_655 ? O3 Na1 O5A 94.4(4) . 2_655 ? O1 Na1 O5A 146.7(4) . . ? O1 Na1 O5A 100.2(4) 2_655 . ? O3 Na1 O5A 94.4(4) 2_655 . ? O3 Na1 O5A 52.4(4) . . ? O5A Na1 O5A 77.7(7) 2_655 . ? O1 Na1 Cl1A 121.07(18) . . ? O1 Na1 Cl1A 108.4(2) 2_655 . ? O3 Na1 Cl1A 117.3(3) 2_655 . ? O3 Na1 Cl1A 26.47(18) . . ? O5A Na1 Cl1A 84.4(4) 2_655 . ? O5A Na1 Cl1A 26.0(3) . . ? O1 Na1 Cl1A 108.4(2) . 2_655 ? O1 Na1 Cl1A 121.07(18) 2_655 2_655 ? O3 Na1 Cl1A 26.46(18) 2_655 2_655 ? O3 Na1 Cl1A 117.3(3) . 2_655 ? O5A Na1 Cl1A 26.0(3) 2_655 2_655 ? O5A Na1 Cl1A 84.4(4) . 2_655 ? Cl1A Na1 Cl1A 100.52(19) . 2_655 ? O1 Na1 Na2 49.42(19) . . ? O1 Na1 Na2 49.42(19) 2_655 . ? O3 Na1 Na2 110.0(2) 2_655 . ? O3 Na1 Na2 110.0(2) . . ? O5A Na1 Na2 141.2(3) 2_655 . ? O5A Na1 Na2 141.2(3) . . ? Cl1A Na1 Na2 129.74(10) . . ? Cl1A Na1 Na2 129.74(10) 2_655 . ? O2 Na2 O2 159.9(4) . 2_655 ? O2 Na2 O6B 111.2(4) . 3 ? O2 Na2 O6B 87.4(4) 2_655 3 ? O2 Na2 O6B 87.4(4) . 4 ? O2 Na2 O6B 111.2(4) 2_655 4 ? O6B Na2 O6B 50.3(8) 3 4 ? O2 Na2 O4A 90.8(5) . 3 ? O2 Na2 O4A 95.7(5) 2_655 3 ? O6B Na2 O4A 50.8(7) 3 3 ? O6B Na2 O4A 93.0(7) 4 3 ? O2 Na2 O4A 95.7(5) . 4 ? O2 Na2 O4A 90.8(5) 2_655 4 ? O6B Na2 O4A 93.0(7) 3 4 ? O6B Na2 O4A 50.8(7) 4 4 ? O4A Na2 O4A 142.7(12) 3 4 ? O2 Na2 O4B 102.8(4) . 4 ? O2 Na2 O4B 86.6(3) 2_655 4 ? O6B Na2 O4B 82.9(5) 3 4 ? O6B Na2 O4B 44.4(5) 4 4 ? O4A Na2 O4B 133.3(7) 3 4 ? O4A Na2 O4B 10.8(7) 4 4 ? O2 Na2 O4B 86.6(3) . 3 ? O2 Na2 O4B 102.8(4) 2_655 3 ? O6B Na2 O4B 44.4(5) 3 3 ? O6B Na2 O4B 82.9(5) 4 3 ? O4A Na2 O4B 10.8(7) 3 3 ? O4A Na2 O4B 133.3(7) 4 3 ? O4B Na2 O4B 124.9(7) 4 3 ? O2 Na2 Cl1B 102.14(18) . 3 ? O2 Na2 Cl1B 91.32(17) 2_655 3 ? O6B Na2 Cl1B 26.1(4) 3 3 ? O6B Na2 Cl1B 71.9(4) 4 3 ? O4A Na2 Cl1B 24.7(6) 3 3 ? O4A Na2 Cl1B 118.8(6) 4 3 ? O4B Na2 Cl1B 108.9(4) 4 3 ? O4B Na2 Cl1B 19.7(3) 3 3 ? O2 Na2 Cl1B 91.32(17) . 4 ? O2 Na2 Cl1B 102.14(18) 2_655 4 ? O6B Na2 Cl1B 71.9(4) 3 4 ? O6B Na2 Cl1B 26.1(4) 4 4 ? O4A Na2 Cl1B 118.8(6) 3 4 ? O4A Na2 Cl1B 24.7(6) 4 4 ? O4B Na2 Cl1B 19.7(3) 4 4 ? O4B Na2 Cl1B 108.9(4) 3 4 ? Cl1B Na2 Cl1B 96.3(2) 3 4 ? O2 Na2 S1 23.56(14) . . ? O2 Na2 S1 137.3(2) 2_655 . ? O6B Na2 S1 134.8(4) 3 . ? O6B Na2 S1 103.8(4) 4 . ? O4A Na2 S1 106.3(5) 3 . ? O4A Na2 S1 93.0(5) 4 . ? O4B Na2 S1 102.8(3) 4 . ? O4B Na2 S1 105.1(3) 3 . ? Cl1B Na2 S1 123.05(9) 3 . ? Cl1B Na2 S1 98.62(9) 4 . ? O2 Na2 S1 137.3(2) . 2_655 ? O2 Na2 S1 23.56(14) 2_655 2_655 ? O6B Na2 S1 103.8(4) 3 2_655 ? O6B Na2 S1 134.8(4) 4 2_655 ? O4A Na2 S1 93.0(5) 3 2_655 ? O4A Na2 S1 106.3(5) 4 2_655 ? O4B Na2 S1 105.1(3) 4 2_655 ? O4B Na2 S1 102.8(3) 3 2_655 ? Cl1B Na2 S1 98.62(9) 3 2_655 ? Cl1B Na2 S1 123.05(9) 4 2_655 ? S1 Na2 S1 117.21(16) . 2_655 ? Cl1A O3 Na1 103.8(4) . . ? Cl1B O3 Na1 116.5(5) . . ? O5A Cl1A O6A 111.6(9) . . ? O5A Cl1A O3 108.7(8) . . ? O6A Cl1A O3 115.2(7) . . ? O5A Cl1A O4A 99.1(11) . . ? O6A Cl1A O4A 100.6(11) . . ? O3 Cl1A O4A 120.6(9) . . ? O5A Cl1A Na1 59.1(7) . . ? O6A Cl1A Na1 136.3(7) . . ? O3 Cl1A Na1 49.7(3) . . ? O4A Cl1A Na1 122.6(9) . . ? Cl1A O4A Na2 114.5(12) . 3_445 ? Cl1A O5A Na1 94.9(8) . . ? O4B Cl1B O5B 130.8(11) . . ? O4B Cl1B O6B 93.4(12) . . ? O5B Cl1B O6B 105.7(9) . . ? O4B Cl1B O3 119.7(9) . . ? O5B Cl1B O3 103.4(8) . . ? O6B Cl1B O3 95.4(8) . . ? O4B Cl1B Na2 51.1(9) . 3_445 ? O5B Cl1B Na2 117.2(7) . 3_445 ? O6B Cl1B Na2 46.0(7) . 3_445 ? O3 Cl1B Na2 128.8(4) . 3_445 ? Cl1B O4B Na2 109.2(11) . 3_445 ? Cl1B O6B Na2 107.9(10) . 3_445 ? O9B Cl2 O10A 130.1(12) . . ? O9B Cl2 O7 111.1(9) . . ? O10A Cl2 O7 116.0(9) . . ? O9B Cl2 O8B 116.5(11) . . ? O10A Cl2 O8B 54.2(11) . . ? O7 Cl2 O8B 116.1(8) . . ? O10A Cl2 O9A 105.2(11) . . ? O7 Cl2 O9A 113.7(8) . . ? O8B Cl2 O9A 130.1(9) . . ? O9B Cl2 O8A 71.5(10) . . ? O10A Cl2 O8A 111.1(11) . . ? O7 Cl2 O8A 103.5(6) . . ? O8B Cl2 O8A 58.3(9) . . ? O9A Cl2 O8A 107.1(9) . . ? O9B Cl2 O10B 108.6(11) . . ? O10A Cl2 O10B 49.1(10) . . ? O7 Cl2 O10B 99.1(8) . . ? O8B Cl2 O10B 103.3(10) . . ? O9A Cl2 O10B 71.2(10) . . ? O8A Cl2 O10B 155.5(9) . . ? 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 N4 Os1 S1 O2 8.1(3) . . . . ? N2 Os1 S1 O2 -89.1(3) . . . . ? N3 Os1 S1 O2 -167.3(3) . . . . ? N1 Os1 S1 O2 93.8(3) . . . . ? N4 Os1 S1 O1 140.7(4) . . . . ? N2 Os1 S1 O1 43.6(4) . . . . ? N3 Os1 S1 O1 -34.7(4) . . . . ? N1 Os1 S1 O1 -133.6(4) . . . . ? N4 Os1 S1 C1 -106.1(3) . . . . ? N2 Os1 S1 C1 156.8(3) . . . . ? N3 Os1 S1 C1 78.5(3) . . . . ? N1 Os1 S1 C1 -20.4(4) . . . . ? N4 Os1 S1 Na2 55.50(19) . . . . ? N2 Os1 S1 Na2 -41.63(19) . . . . ? N3 Os1 S1 Na2 -119.87(19) . . . . ? N1 Os1 S1 Na2 141.2(2) . . . . ? O2 S1 O1 Na1 -84.2(14) . . . . ? C1 S1 O1 Na1 27.8(14) . . . . ? Os1 S1 O1 Na1 137.9(12) . . . . ? Na2 S1 O1 Na1 -94.7(13) . . . . ? O1 S1 O2 Na2 -15.5(5) . . . . ? C1 S1 O2 Na2 -128.0(4) . . . . ? Os1 S1 O2 Na2 120.2(2) . . . . ? N4 Os1 N1 C2 99.3(5) . . . . ? N3 Os1 N1 C2 -89.9(5) . . . . ? N5 Os1 N1 C2 176.4(5) . . . . ? S1 Os1 N1 C2 -2.9(5) . . . . ? O2 S1 C1 C2 -82.2(6) . . . . ? O1 S1 C1 C2 163.4(6) . . . . ? Os1 S1 C1 C2 42.9(6) . . . . ? Na2 S1 C1 C2 -120.3(5) . . . . ? S1 C1 C2 N1 -51.3(9) . . . . ? Os1 N1 C2 C1 32.5(8) . . . . ? N4 Os1 N2 C7 167.8(5) . . . . ? N3 Os1 N2 C7 -2.8(4) . . . . ? N5 Os1 N2 C7 90.8(5) . . . . ? S1 Os1 N2 C7 -89.8(4) . . . . ? N4 Os1 N2 C3 -10.1(6) . . . . ? N3 Os1 N2 C3 179.3(6) . . . . ? N5 Os1 N2 C3 -87.1(6) . . . . ? S1 Os1 N2 C3 92.3(5) . . . . ? C7 N2 C3 C4 -0.6(11) . . . . ? Os1 N2 C3 C4 177.3(6) . . . . ? N2 C3 C4 C5 -0.5(12) . . . . ? C3 C4 C5 C6 0.8(12) . . . . ? C4 C5 C6 C7 -0.1(11) . . . . ? C3 N2 C7 C6 1.3(10) . . . . ? Os1 N2 C7 C6 -176.8(5) . . . . ? C3 N2 C7 C8 -178.4(6) . . . . ? Os1 N2 C7 C8 3.5(7) . . . . ? C5 C6 C7 N2 -1.0(11) . . . . ? C5 C6 C7 C8 178.7(7) . . . . ? N2 C7 C8 N3 -2.2(9) . . . . ? C6 C7 C8 N3 178.1(6) . . . . ? N2 C7 C8 C9 178.3(6) . . . . ? C6 C7 C8 C9 -1.3(11) . . . . ? N3 C8 C9 C10 0.0(11) . . . . ? C7 C8 C9 C10 179.4(7) . . . . ? C8 C9 C10 C11 -0.5(12) . . . . ? C9 C10 C11 C12 0.0(12) . . . . ? C10 C11 C12 N3 0.9(13) . . . . ? C9 C8 N3 C12 0.9(10) . . . . ? C7 C8 N3 C12 -178.6(6) . . . . ? C9 C8 N3 Os1 179.3(5) . . . . ? C7 C8 N3 Os1 -0.2(7) . . . . ? C11 C12 N3 C8 -1.3(11) . . . . ? C11 C12 N3 Os1 -179.5(6) . . . . ? N4 Os1 N3 C8 -59.2(12) . . . . ? N2 Os1 N3 C8 1.5(4) . . . . ? N5 Os1 N3 C8 -84.3(5) . . . . ? N1 Os1 N3 C8 -179.9(5) . . . . ? S1 Os1 N3 C8 95.7(4) . . . . ? N4 Os1 N3 C12 119.0(11) . . . . ? N2 Os1 N3 C12 179.8(6) . . . . ? N5 Os1 N3 C12 93.9(6) . . . . ? N1 Os1 N3 C12 -1.6(6) . . . . ? S1 Os1 N3 C12 -86.0(6) . . . . ? N2 Os1 N4 C13 102.5(5) . . . . ? N3 Os1 N4 C13 161.8(10) . . . . ? N5 Os1 N4 C13 -172.5(6) . . . . ? N1 Os1 N4 C13 -76.6(6) . . . . ? S1 Os1 N4 C13 7.4(6) . . . . ? N2 Os1 N4 C17 -77.1(4) . . . . ? N3 Os1 N4 C17 -17.8(13) . . . . ? N5 Os1 N4 C17 8.0(4) . . . . ? N1 Os1 N4 C17 103.8(5) . . . . ? S1 Os1 N4 C17 -172.2(4) . . . . ? C17 N4 C13 C14 -0.8(10) . . . . ? Os1 N4 C13 C14 179.6(6) . . . . ? N4 C13 C14 C15 -0.3(12) . . . . ? C13 C14 C15 C16 1.0(12) . . . . ? C14 C15 C16 C17 -0.7(12) . . . . ? C13 N4 C17 C16 1.2(9) . . . . ? Os1 N4 C17 C16 -179.2(5) . . . . ? C13 N4 C17 C18 176.9(6) . . . . ? Os1 N4 C17 C18 -3.5(7) . . . . ? C15 C16 C17 N4 -0.4(11) . . . . ? C15 C16 C17 C18 -175.8(7) . . . . ? N4 C17 C18 N5 -6.6(8) . . . . ? C16 C17 C18 N5 169.1(6) . . . . ? N4 C17 C18 C19 171.7(7) . . . . ? C16 C17 C18 C19 -12.6(11) . . . . ? N5 C18 C19 C20 -3.5(11) . . . . ? C17 C18 C19 C20 178.3(7) . . . . ? C18 C19 C20 C21 -1.3(12) . . . . ? C19 C20 C21 C22 4.0(11) . . . . ? C20 C21 C22 N5 -2.2(11) . . . . ? C19 C18 N5 C22 5.4(10) . . . . ? C17 C18 N5 C22 -176.3(5) . . . . ? C19 C18 N5 Os1 -165.0(6) . . . . ? C17 C18 N5 Os1 13.3(7) . . . . ? C21 C22 N5 C18 -2.5(10) . . . . ? C21 C22 N5 Os1 166.7(5) . . . . ? N4 Os1 N5 C18 -11.6(5) . . . . ? N2 Os1 N5 C18 85.5(5) . . . . ? N3 Os1 N5 C18 163.7(5) . . . . ? N1 Os1 N5 C18 -97.3(5) . . . . ? N4 Os1 N5 C22 178.9(6) . . . . ? N2 Os1 N5 C22 -84.0(6) . . . . ? N3 Os1 N5 C22 -5.8(6) . . . . ? N1 Os1 N5 C22 93.2(6) . . . . ? S1 O1 Na1 O1 92.4(13) . . . 2_655 ? S1 O1 Na1 O3 -6.7(14) . . . 2_655 ? S1 O1 Na1 O3 -155.7(13) . . . . ? S1 O1 Na1 O5A -60.2(14) . . . 2_655 ? S1 O1 Na1 O5A -143.3(12) . . . . ? S1 O1 Na1 Cl1A -149.8(12) . . . . ? S1 O1 Na1 Cl1A -34.7(14) . . . 2_655 ? S1 O1 Na1 Na2 92.4(13) . . . . ? S1 O2 Na2 O2 23.6(3) . . . 2_655 ? S1 O2 Na2 O6B -179.9(5) . . . 3 ? S1 O2 Na2 O6B -134.6(5) . . . 4 ? S1 O2 Na2 O4A 132.4(7) . . . 3 ? S1 O2 Na2 O4A -84.4(7) . . . 4 ? S1 O2 Na2 O4B -92.7(5) . . . 4 ? S1 O2 Na2 O4B 142.3(5) . . . 3 ? S1 O2 Na2 Cl1B 154.5(3) . . . 3 ? S1 O2 Na2 Cl1B -108.8(3) . . . 4 ? S1 O2 Na2 S1 37.2(5) . . . 2_655 ? O1 S1 Na2 O2 164.4(5) . . . . ? C1 S1 Na2 O2 68.9(5) . . . . ? Os1 S1 Na2 O2 -88.7(4) . . . . ? O2 S1 Na2 O2 -168.3(2) . . . 2_655 ? O1 S1 Na2 O2 -3.9(3) . . . 2_655 ? C1 S1 Na2 O2 -99.4(4) . . . 2_655 ? Os1 S1 Na2 O2 103.0(2) . . . 2_655 ? O2 S1 Na2 O6B 0.1(7) . . . 3 ? O1 S1 Na2 O6B 164.5(6) . . . 3 ? C1 S1 Na2 O6B 69.1(7) . . . 3 ? Os1 S1 Na2 O6B -88.6(5) . . . 3 ? O2 S1 Na2 O6B 47.1(5) . . . 4 ? O1 S1 Na2 O6B -148.6(5) . . . 4 ? C1 S1 Na2 O6B 116.0(5) . . . 4 ? Os1 S1 Na2 O6B -41.7(4) . . . 4 ? O2 S1 Na2 O4A -50.3(7) . . . 3 ? O1 S1 Na2 O4A 114.0(7) . . . 3 ? C1 S1 Na2 O4A 18.6(7) . . . 3 ? Os1 S1 Na2 O4A -139.1(6) . . . 3 ? O2 S1 Na2 O4A 97.3(7) . . . 4 ? O1 S1 Na2 O4A -98.3(6) . . . 4 ? C1 S1 Na2 O4A 166.3(7) . . . 4 ? Os1 S1 Na2 O4A 8.6(6) . . . 4 ? O2 S1 Na2 O4B 92.8(5) . . . 4 ? O1 S1 Na2 O4B -102.9(4) . . . 4 ? C1 S1 Na2 O4B 161.7(5) . . . 4 ? Os1 S1 Na2 O4B 4.0(4) . . . 4 ? O2 S1 Na2 O4B -39.2(5) . . . 3 ? O1 S1 Na2 O4B 125.2(5) . . . 3 ? C1 S1 Na2 O4B 29.7(5) . . . 3 ? Os1 S1 Na2 O4B -127.9(4) . . . 3 ? O2 S1 Na2 Cl1B -30.2(4) . . . 3 ? O1 S1 Na2 Cl1B 134.2(3) . . . 3 ? C1 S1 Na2 Cl1B 38.8(4) . . . 3 ? Os1 S1 Na2 Cl1B -118.89(14) . . . 3 ? O2 S1 Na2 Cl1B 73.2(4) . . . 4 ? O1 S1 Na2 Cl1B -122.5(3) . . . 4 ? C1 S1 Na2 Cl1B 142.1(4) . . . 4 ? Os1 S1 Na2 Cl1B -15.56(17) . . . 4 ? O2 S1 Na2 S1 -152.6(4) . . . 2_655 ? O1 S1 Na2 S1 11.8(3) . . . 2_655 ? C1 S1 Na2 S1 -83.6(4) . . . 2_655 ? Os1 S1 Na2 S1 118.72(11) . . . 2_655 ? O1 Na1 O3 Cl1A 168.7(5) . . . . ? O1 Na1 O3 Cl1A -89.7(5) 2_655 . . . ? O3 Na1 O3 Cl1A 37.3(4) 2_655 . . . ? O5A Na1 O3 Cl1A 68.0(6) 2_655 . . . ? O5A Na1 O3 Cl1A -2.7(5) . . . . ? Cl1A Na1 O3 Cl1A 55.0(5) 2_655 . . . ? Na2 Na1 O3 Cl1A -142.7(4) . . . . ? O1 Na1 O3 Cl1B 156.9(5) . . . . ? O1 Na1 O3 Cl1B -101.6(5) 2_655 . . . ? O3 Na1 O3 Cl1B 25.4(4) 2_655 . . . ? O5A Na1 O3 Cl1B 56.2(6) 2_655 . . . ? O5A Na1 O3 Cl1B -14.6(5) . . . . ? Cl1A Na1 O3 Cl1B -11.9(3) . . . . ? Cl1A Na1 O3 Cl1B 43.1(5) 2_655 . . . ? Na2 Na1 O3 Cl1B -154.6(4) . . . . ? Cl1B O3 Cl1A O5A 145.1(14) . . . . ? Na1 O3 Cl1A O5A 4.5(8) . . . . ? Cl1B O3 Cl1A O6A -88.9(13) . . . . ? Na1 O3 Cl1A O6A 130.5(8) . . . . ? Cl1B O3 Cl1A O4A 32.0(13) . . . . ? Na1 O3 Cl1A O4A -108.7(11) . . . . ? Cl1B O3 Cl1A Na1 140.6(10) . . . . ? O1 Na1 Cl1A O5A 171.8(8) . . . . ? O1 Na1 Cl1A O5A -75.2(8) 2_655 . . . ? O3 Na1 Cl1A O5A 30.9(8) 2_655 . . . ? O3 Na1 Cl1A O5A -175.0(9) . . . . ? O5A Na1 Cl1A O5A 73.2(10) 2_655 . . . ? Cl1A Na1 Cl1A O5A 52.7(8) 2_655 . . . ? Na2 Na1 Cl1A O5A -127.3(8) . . . . ? O1 Na1 Cl1A O6A -98.5(10) . . . . ? O1 Na1 Cl1A O6A 14.4(10) 2_655 . . . ? O3 Na1 Cl1A O6A 120.6(10) 2_655 . . . ? O3 Na1 Cl1A O6A -85.4(11) . . . . ? O5A Na1 Cl1A O6A 162.9(10) 2_655 . . . ? O5A Na1 Cl1A O6A 89.6(12) . . . . ? Cl1A Na1 Cl1A O6A 142.4(10) 2_655 . . . ? Na2 Na1 Cl1A O6A -37.6(10) . . . . ? O1 Na1 Cl1A O3 -13.1(5) . . . . ? O1 Na1 Cl1A O3 99.8(5) 2_655 . . . ? O3 Na1 Cl1A O3 -154.0(4) 2_655 . . . ? O5A Na1 Cl1A O3 -111.7(6) 2_655 . . . ? O5A Na1 Cl1A O3 175.0(9) . . . . ? Cl1A Na1 Cl1A O3 -132.2(5) 2_655 . . . ? Na2 Na1 Cl1A O3 47.8(5) . . . . ? O1 Na1 Cl1A O4A 91.3(11) . . . . ? O1 Na1 Cl1A O4A -155.7(10) 2_655 . . . ? O3 Na1 Cl1A O4A -49.6(11) 2_655 . . . ? O3 Na1 Cl1A O4A 104.4(11) . . . . ? O5A Na1 Cl1A O4A -7.3(11) 2_655 . . . ? O5A Na1 Cl1A O4A -80.5(13) . . . . ? Cl1A Na1 Cl1A O4A -27.8(10) 2_655 . . . ? Na2 Na1 Cl1A O4A 152.2(10) . . . . ? O5A Cl1A O4A Na2 156.2(11) . . . 3_445 ? O6A Cl1A O4A Na2 42.1(13) . . . 3_445 ? O3 Cl1A O4A Na2 -85.7(12) . . . 3_445 ? Na1 Cl1A O4A Na2 -144.8(6) . . . 3_445 ? O6A Cl1A O5A Na1 -132.0(7) . . . . ? O3 Cl1A O5A Na1 -4.0(8) . . . . ? O4A Cl1A O5A Na1 122.7(9) . . . . ? O1 Na1 O5A Cl1A -12.8(13) . . . . ? O1 Na1 O5A Cl1A 111.2(7) 2_655 . . . ? O3 Na1 O5A Cl1A -152.7(7) 2_655 . . . ? O3 Na1 O5A Cl1A 2.8(5) . . . . ? O5A Na1 O5A Cl1A -102.7(9) 2_655 . . . ? Cl1A Na1 O5A Cl1A -128.2(7) 2_655 . . . ? Na2 Na1 O5A Cl1A 77.3(9) . . . . ? Cl1A O3 Cl1B O4B -133.8(16) . . . . ? Na1 O3 Cl1B O4B -90.3(11) . . . . ? Cl1A O3 Cl1B O5B 21.6(11) . . . . ? Na1 O3 Cl1B O5B 65.1(9) . . . . ? Cl1A O3 Cl1B O6B 129.2(13) . . . . ? Na1 O3 Cl1B O6B 172.7(8) . . . . ? Cl1A O3 Cl1B Na2 164.2(13) . . . 3_445 ? Na1 O3 Cl1B Na2 -152.3(3) . . . 3_445 ? O5B Cl1B O4B Na2 94.6(14) . . . 3_445 ? O6B Cl1B O4B Na2 -19.6(10) . . . 3_445 ? O3 Cl1B O4B Na2 -117.8(8) . . . 3_445 ? O4B Cl1B O6B Na2 21.3(11) . . . 3_445 ? O5B Cl1B O6B Na2 -112.9(9) . . . 3_445 ? O3 Cl1B O6B Na2 141.5(7) . . . 3_445 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O10B 0.87(9) 2.17(9) 2.973(19) 153(7) 3 N1 H2 O7 0.79(8) 2.23(8) 2.989(10) 163(8) 7 N1 H1 O10A 0.87(9) 2.61(9) 3.46(2) 163(8) 3 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.850 _refine_diff_density_min -1.915 _refine_diff_density_rms 0.179 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. ; #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 834771' #TrackingRef 'web_deposit_cif_file_0_AsakoIgashira_1310689294.konno.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 F12 N6 O2 Os P2 S' _chemical_formula_weight 916.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Os Os -1.2165 7.6030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 15.9170(3) _cell_length_b 9.4043(2) _cell_length_c 20.2031(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.5150(10) _cell_angle_gamma 90.00 _cell_volume 2973.38(11) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 23485 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 4.577 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.432 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28325 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6779 _reflns_number_gt 6065 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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^)+(0.0331P)^2^+2.2534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6779 _refine_ls_number_parameters 467 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Os1 Os 0.249696(7) 0.679485(12) 0.043693(5) 0.02278(5) Uani 1 1 d . . . S1 S 0.32778(5) 0.85833(9) 0.01498(4) 0.02829(16) Uani 1 1 d . . . O1 O 0.3385(2) 0.8600(3) -0.05631(12) 0.0570(8) Uani 1 1 d . . . O2 O 0.41099(16) 0.8908(3) 0.05844(12) 0.0407(6) Uani 1 1 d . . . N1 N 0.1619(2) 0.8400(3) 0.04797(15) 0.0319(6) Uani 1 1 d . . . H1 H 0.122(3) 0.821(4) 0.060(2) 0.038 Uiso 1 1 d . . . C1 C 0.2626(3) 1.0140(4) 0.0250(3) 0.0582(11) Uani 1 1 d . . . H2 H 0.2946 1.0773 0.0599 0.070 Uiso 1 1 calc R . . H3 H 0.2506 1.0675 -0.0178 0.070 Uiso 1 1 calc R . . C2 C 0.1820(3) 0.9724(5) 0.0445(2) 0.0550(11) Uani 1 1 d . . . H4 H 0.1439 1.0437 0.0546 0.066 Uiso 1 1 calc R . . N2 N 0.33834(17) 0.5246(3) 0.03320(12) 0.0273(5) Uani 1 1 d . . . C3 C 0.4078(2) 0.4904(4) 0.07929(16) 0.0344(7) Uani 1 1 d . . . H5 H 0.4176 0.5393 0.1211 0.041 Uiso 1 1 calc R . . C4 C 0.4652(2) 0.3875(4) 0.06816(19) 0.0431(9) Uani 1 1 d . . . H6 H 0.5140 0.3672 0.1015 0.052 Uiso 1 1 calc R . . C5 C 0.4510(3) 0.3136(4) 0.0075(2) 0.0482(10) Uani 1 1 d . . . H7 H 0.4889 0.2406 -0.0009 0.058 Uiso 1 1 calc R . . C6 C 0.3807(3) 0.3487(4) -0.03997(19) 0.0418(9) Uani 1 1 d . . . H8 H 0.3701 0.3003 -0.0819 0.050 Uiso 1 1 calc R . . C7 C 0.3256(2) 0.4540(3) -0.02699(15) 0.0299(7) Uani 1 1 d . . . C8 C 0.2526(2) 0.5072(3) -0.07638(15) 0.0280(6) Uani 1 1 d . . . C9 C 0.2265(2) 0.4474(4) -0.13968(16) 0.0375(8) Uani 1 1 d . . . H9 H 0.2544 0.3653 -0.1524 0.045 Uiso 1 1 calc R . . C10 C 0.1597(2) 0.5081(4) -0.18396(17) 0.0413(8) Uani 1 1 d . . . H10 H 0.1404 0.4671 -0.2270 0.050 Uiso 1 1 calc R . . C11 C 0.1216(2) 0.6289(4) -0.16464(16) 0.0382(8) Uani 1 1 d . . . H11 H 0.0768 0.6742 -0.1948 0.046 Uiso 1 1 calc R . . C12 C 0.1493(2) 0.6835(4) -0.10093(16) 0.0315(7) Uani 1 1 d . . . H12 H 0.1226 0.7667 -0.0879 0.038 Uiso 1 1 calc R . . N3 N 0.21264(17) 0.6231(3) -0.05664(12) 0.0252(5) Uani 1 1 d . . . N4 N 0.27880(18) 0.6977(3) 0.14846(13) 0.0276(6) Uani 1 1 d . . . C13 C 0.3363(2) 0.7870(4) 0.18421(16) 0.0346(7) Uani 1 1 d . . . H13 H 0.3712 0.8428 0.1609 0.042 Uiso 1 1 calc R . . C14 C 0.3465(3) 0.8005(4) 0.25319(17) 0.0380(8) Uani 1 1 d . . . H14 H 0.3882 0.8637 0.2766 0.046 Uiso 1 1 calc R . . C15 C 0.2962(2) 0.7226(4) 0.28754(16) 0.0390(8) Uani 1 1 d . . . H15 H 0.3006 0.7339 0.3348 0.047 Uiso 1 1 calc R . . C16 C 0.2391(2) 0.6276(4) 0.25259(16) 0.0366(8) Uani 1 1 d . . . H16 H 0.2051 0.5700 0.2759 0.044 Uiso 1 1 calc R . . C17 C 0.2312(2) 0.6156(4) 0.18360(15) 0.0297(7) Uani 1 1 d . . . C18 C 0.1736(2) 0.5133(4) 0.14296(16) 0.0304(7) Uani 1 1 d . . . C19 C 0.1299(2) 0.4087(4) 0.17097(18) 0.0408(8) Uani 1 1 d . . . H17 H 0.1343 0.4028 0.2184 0.049 Uiso 1 1 calc R . . C20 C 0.0797(3) 0.3122(4) 0.1292(2) 0.0434(9) Uani 1 1 d . . . H18 H 0.0499 0.2388 0.1474 0.052 Uiso 1 1 calc R . . C21 C 0.0740(2) 0.3256(4) 0.0607(2) 0.0393(8) Uani 1 1 d . . . H19 H 0.0392 0.2622 0.0309 0.047 Uiso 1 1 calc R . . C22 C 0.1192(2) 0.4312(4) 0.03553(17) 0.0352(7) Uani 1 1 d . . . H20 H 0.1147 0.4393 -0.0119 0.042 Uiso 1 1 calc R . . N5 N 0.16978(17) 0.5235(3) 0.07558(13) 0.0283(6) Uani 1 1 d . . . N6 N 0.5521(2) 1.0180(4) 0.12779(16) 0.0424(7) Uani 1 1 d D . . H21 H 0.532(3) 1.095(5) 0.151(2) 0.064 Uiso 1 1 d D . . H22 H 0.506(3) 0.977(5) 0.102(2) 0.064 Uiso 1 1 d D . . H23 H 0.584(3) 1.064(5) 0.096(2) 0.064 Uiso 1 1 d D . . H24 H 0.578(3) 0.955(5) 0.156(2) 0.064 Uiso 1 1 d D . . P1 P 0.37596(7) 0.23655(12) 0.23490(5) 0.0466(2) Uani 1 1 d . . . F1 F 0.4459(2) 0.3577(4) 0.24234(18) 0.0989(12) Uani 1 1 d . . . F2 F 0.3244(2) 0.3147(3) 0.17168(16) 0.0813(9) Uani 1 1 d . . . F3 F 0.4257(2) 0.1506(4) 0.18706(17) 0.0935(11) Uani 1 1 d . . . F4 F 0.3035(2) 0.1202(3) 0.22691(16) 0.0894(10) Uani 1 1 d . . . F5 F 0.4254(3) 0.1564(4) 0.29855(17) 0.1117(15) Uani 1 1 d . . . F6 F 0.3266(2) 0.3226(3) 0.28502(16) 0.0717(8) Uani 1 1 d . . . P2 P 0.03665(7) 0.38114(12) 0.36258(5) 0.0414(2) Uani 1 1 d . . . F7 F 0.0475(2) 0.2894(3) 0.29910(13) 0.0645(7) Uani 1 1 d . A . F8 F 0.02396(19) 0.4729(3) 0.42685(13) 0.0795(9) Uani 1 1 d . A . F9A F 0.0403(11) 0.5194(18) 0.3138(8) 0.091(5) Uani 0.50 1 d P A 1 F10A F 0.1335(10) 0.389(2) 0.3820(8) 0.129(7) Uani 0.50 1 d P A 1 F11A F 0.0267(10) 0.2550(16) 0.4050(7) 0.110(6) Uani 0.50 1 d P A 1 F12A F -0.0634(10) 0.384(2) 0.3353(8) 0.087(5) Uani 0.50 1 d P A 1 F9B F 0.0770(10) 0.5124(16) 0.3385(8) 0.101(6) Uani 0.50 1 d P A 2 F10B F 0.1274(9) 0.3264(14) 0.4028(7) 0.081(4) Uani 0.50 1 d P A 2 F11B F -0.0034(8) 0.2409(16) 0.3932(7) 0.073(4) Uani 0.50 1 d P A 2 F12B F -0.0558(9) 0.4248(19) 0.3309(9) 0.083(5) Uani 0.50 1 d P 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 Os1 0.02255(8) 0.02916(8) 0.01810(7) -0.00136(4) 0.00759(4) -0.00008(4) S1 0.0289(4) 0.0346(4) 0.0228(3) -0.0003(3) 0.0084(3) -0.0036(3) O1 0.073(2) 0.078(2) 0.0241(12) -0.0063(13) 0.0185(13) -0.0406(17) O2 0.0347(14) 0.0481(15) 0.0388(13) -0.0033(12) 0.0048(10) -0.0120(12) N1 0.0258(15) 0.0427(17) 0.0297(14) -0.0026(12) 0.0115(12) 0.0012(12) C1 0.048(3) 0.036(2) 0.093(3) 0.008(2) 0.018(2) 0.0041(18) C2 0.068(3) 0.046(2) 0.060(3) 0.008(2) 0.035(2) 0.022(2) N2 0.0267(14) 0.0313(13) 0.0254(12) 0.0035(11) 0.0090(10) 0.0026(11) C3 0.0339(18) 0.0430(19) 0.0275(15) 0.0056(14) 0.0088(13) 0.0035(15) C4 0.038(2) 0.049(2) 0.043(2) 0.0131(18) 0.0083(16) 0.0140(17) C5 0.051(3) 0.047(2) 0.052(2) 0.0099(18) 0.022(2) 0.0211(18) C6 0.050(2) 0.043(2) 0.0355(18) -0.0035(16) 0.0168(17) 0.0110(17) C7 0.0376(18) 0.0300(16) 0.0250(14) 0.0020(13) 0.0136(13) -0.0017(14) C8 0.0290(17) 0.0305(16) 0.0273(15) -0.0001(13) 0.0126(12) -0.0015(13) C9 0.050(2) 0.0382(18) 0.0269(15) -0.0062(14) 0.0130(14) -0.0032(16) C10 0.046(2) 0.052(2) 0.0254(15) -0.0088(16) 0.0054(14) -0.0074(17) C11 0.0309(19) 0.056(2) 0.0262(16) 0.0025(16) 0.0018(13) -0.0037(16) C12 0.0269(17) 0.0442(19) 0.0238(15) 0.0000(13) 0.0057(12) 0.0021(14) N3 0.0249(13) 0.0313(13) 0.0213(11) 0.0003(11) 0.0088(10) -0.0021(11) N4 0.0297(15) 0.0323(14) 0.0219(12) -0.0010(11) 0.0079(10) 0.0007(11) C13 0.040(2) 0.0372(18) 0.0264(16) -0.0021(14) 0.0061(14) -0.0062(15) C14 0.044(2) 0.043(2) 0.0250(16) -0.0047(14) 0.0013(14) 0.0002(16) C15 0.048(2) 0.049(2) 0.0208(15) 0.0037(15) 0.0077(14) 0.0160(17) C16 0.044(2) 0.0420(19) 0.0267(16) 0.0057(15) 0.0154(14) 0.0060(16) C17 0.0303(17) 0.0328(16) 0.0290(15) 0.0025(14) 0.0135(13) 0.0071(13) C18 0.0286(17) 0.0358(17) 0.0303(15) 0.0019(14) 0.0144(13) 0.0035(13) C19 0.042(2) 0.049(2) 0.0357(18) 0.0051(17) 0.0198(15) -0.0041(17) C20 0.036(2) 0.044(2) 0.055(2) 0.0062(17) 0.0220(18) -0.0057(16) C21 0.032(2) 0.040(2) 0.048(2) -0.0057(16) 0.0138(16) -0.0094(15) C22 0.0332(19) 0.0404(19) 0.0341(17) -0.0052(15) 0.0120(14) -0.0051(15) N5 0.0271(14) 0.0318(14) 0.0289(13) -0.0018(11) 0.0130(10) -0.0011(11) N6 0.0412(19) 0.054(2) 0.0326(16) -0.0018(15) 0.0078(13) -0.0136(16) P1 0.0550(7) 0.0447(6) 0.0452(5) -0.0003(5) 0.0227(5) 0.0063(5) F1 0.088(2) 0.127(3) 0.093(2) -0.031(2) 0.045(2) -0.053(2) F2 0.068(2) 0.100(2) 0.079(2) 0.0374(16) 0.0232(16) 0.0181(16) F3 0.105(3) 0.107(2) 0.077(2) -0.0106(18) 0.042(2) 0.046(2) F4 0.128(3) 0.0667(18) 0.083(2) -0.0129(16) 0.043(2) -0.0384(19) F5 0.118(3) 0.158(4) 0.0602(19) 0.034(2) 0.018(2) 0.065(3) F6 0.084(2) 0.0605(17) 0.085(2) -0.0155(14) 0.0526(17) -0.0032(13) P2 0.0388(5) 0.0513(6) 0.0361(5) -0.0031(4) 0.0120(4) 0.0004(4) F7 0.094(2) 0.0594(15) 0.0460(14) -0.0074(12) 0.0280(14) 0.0068(14) F8 0.080(2) 0.102(2) 0.0572(15) -0.0369(16) 0.0143(14) 0.0144(17) F9A 0.139(13) 0.054(5) 0.096(9) 0.011(6) 0.060(7) 0.012(7) F10A 0.038(5) 0.215(19) 0.124(12) -0.039(11) -0.013(6) 0.009(9) F11A 0.201(17) 0.080(8) 0.048(4) 0.044(5) 0.022(8) 0.025(9) F12A 0.041(5) 0.175(15) 0.049(5) -0.010(7) 0.020(4) -0.016(7) F9B 0.151(15) 0.061(7) 0.115(11) -0.015(7) 0.088(10) -0.050(9) F10B 0.045(5) 0.114(8) 0.078(6) -0.032(5) -0.006(4) 0.032(6) F11B 0.082(6) 0.069(5) 0.082(8) -0.007(5) 0.050(6) -0.028(5) F12B 0.074(10) 0.099(7) 0.064(6) 0.006(4) -0.021(6) 0.048(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 Os1 N2 2.066(3) . ? Os1 N1 2.069(3) . ? Os1 N3 2.074(2) . ? Os1 N4 2.090(3) . ? Os1 N5 2.117(3) . ? Os1 S1 2.2301(8) . ? S1 O1 1.481(2) . ? S1 O2 1.481(2) . ? S1 C1 1.827(4) . ? N1 C2 1.291(5) . ? N1 H1 0.74(4) . ? C1 C2 1.461(6) . ? C1 H2 0.9900 . ? C1 H3 0.9900 . ? C2 H4 0.9500 . ? N2 C3 1.348(4) . ? N2 C7 1.367(4) . ? C3 C4 1.377(5) . ? C3 H5 0.9500 . ? C4 C5 1.390(6) . ? C4 H6 0.9500 . ? C5 C6 1.374(6) . ? C5 H7 0.9500 . ? C6 C7 1.379(5) . ? C6 H8 0.9500 . ? C7 C8 1.474(4) . ? C8 N3 1.358(4) . ? C8 C9 1.389(4) . ? C9 C10 1.381(5) . ? C9 H9 0.9500 . ? C10 C11 1.378(5) . ? C10 H10 0.9500 . ? C11 C12 1.381(5) . ? C11 H11 0.9500 . ? C12 N3 1.346(4) . ? C12 H12 0.9500 . ? N4 C13 1.350(4) . ? N4 C17 1.367(4) . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 C15 1.364(5) . ? C14 H14 0.9500 . ? C15 C16 1.375(5) . ? C15 H15 0.9500 . ? C16 C17 1.381(4) . ? C16 H16 0.9500 . ? C17 C18 1.472(5) . ? C18 N5 1.355(4) . ? C18 C19 1.384(5) . ? C19 C20 1.388(6) . ? C19 H17 0.9500 . ? C20 C21 1.376(6) . ? C20 H18 0.9500 . ? C21 C22 1.377(5) . ? C21 H19 0.9500 . ? C22 N5 1.348(4) . ? C22 H20 0.9500 . ? N6 H21 0.95(4) . ? N6 H22 0.90(4) . ? N6 H23 0.99(4) . ? N6 H24 0.87(4) . ? P1 F2 1.569(3) . ? P1 F5 1.572(3) . ? P1 F4 1.577(3) . ? P1 F3 1.579(3) . ? P1 F1 1.580(3) . ? P1 F6 1.608(3) . ? P2 F11A 1.489(11) . ? P2 F9B 1.513(14) . ? P2 F10A 1.521(16) . ? P2 F12B 1.549(13) . ? P2 F7 1.581(3) . ? P2 F12A 1.588(16) . ? P2 F8 1.602(3) . ? P2 F10B 1.608(14) . ? P2 F11B 1.635(12) . ? P2 F9A 1.638(16) . ? 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 N2 Os1 N1 176.14(10) . . ? N2 Os1 N3 78.29(10) . . ? N1 Os1 N3 98.84(11) . . ? N2 Os1 N4 97.61(10) . . ? N1 Os1 N4 85.67(11) . . ? N3 Os1 N4 169.07(10) . . ? N2 Os1 N5 90.13(11) . . ? N1 Os1 N5 92.59(11) . . ? N3 Os1 N5 92.33(10) . . ? N4 Os1 N5 77.46(10) . . ? N2 Os1 S1 94.68(8) . . ? N1 Os1 S1 82.71(9) . . ? N3 Os1 S1 90.65(7) . . ? N4 Os1 S1 99.83(8) . . ? N5 Os1 S1 174.78(7) . . ? O1 S1 O2 109.00(16) . . ? O1 S1 C1 105.6(2) . . ? O2 S1 C1 103.52(19) . . ? O1 S1 Os1 115.42(11) . . ? O2 S1 Os1 118.79(11) . . ? C1 S1 Os1 102.73(14) . . ? C2 N1 Os1 121.7(3) . . ? C2 N1 H1 119(3) . . ? Os1 N1 H1 117(3) . . ? C2 C1 S1 111.1(3) . . ? C2 C1 H2 109.4 . . ? S1 C1 H2 109.4 . . ? C2 C1 H3 109.4 . . ? S1 C1 H3 109.4 . . ? H2 C1 H3 108.0 . . ? N1 C2 C1 120.7(4) . . ? N1 C2 H4 119.6 . . ? C1 C2 H4 119.6 . . ? C3 N2 C7 117.9(3) . . ? C3 N2 Os1 125.9(2) . . ? C7 N2 Os1 116.1(2) . . ? N2 C3 C4 122.6(3) . . ? N2 C3 H5 118.7 . . ? C4 C3 H5 118.7 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H6 120.4 . . ? C5 C4 H6 120.4 . . ? C6 C5 C4 118.4(3) . . ? C6 C5 H7 120.8 . . ? C4 C5 H7 120.8 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H8 119.9 . . ? C7 C6 H8 119.9 . . ? N2 C7 C6 121.4(3) . . ? N2 C7 C8 114.1(3) . . ? C6 C7 C8 124.4(3) . . ? N3 C8 C9 121.1(3) . . ? N3 C8 C7 115.3(3) . . ? C9 C8 C7 123.5(3) . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 118.9(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N3 C12 C11 122.4(3) . . ? N3 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 N3 C8 118.6(3) . . ? C12 N3 Os1 125.9(2) . . ? C8 N3 Os1 115.3(2) . . ? C13 N4 C17 117.3(3) . . ? C13 N4 Os1 126.6(2) . . ? C17 N4 Os1 116.0(2) . . ? N4 C13 C14 122.8(3) . . ? N4 C13 H13 118.6 . . ? C14 C13 H13 118.6 . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? N4 C17 C16 121.4(3) . . ? N4 C17 C18 115.3(3) . . ? C16 C17 C18 123.3(3) . . ? N5 C18 C19 121.8(3) . . ? N5 C18 C17 115.0(3) . . ? C19 C18 C17 123.0(3) . . ? C18 C19 C20 119.5(3) . . ? C18 C19 H17 120.3 . . ? C20 C19 H17 120.3 . . ? C21 C20 C19 118.5(3) . . ? C21 C20 H18 120.8 . . ? C19 C20 H18 120.8 . . ? C20 C21 C22 119.6(3) . . ? C20 C21 H19 120.2 . . ? C22 C21 H19 120.2 . . ? N5 C22 C21 122.5(3) . . ? N5 C22 H20 118.7 . . ? C21 C22 H20 118.7 . . ? C22 N5 C18 118.0(3) . . ? C22 N5 Os1 126.1(2) . . ? C18 N5 Os1 115.8(2) . . ? H21 N6 H22 107(4) . . ? H21 N6 H23 104(4) . . ? H22 N6 H23 106(4) . . ? H21 N6 H24 111(4) . . ? H22 N6 H24 109(4) . . ? H23 N6 H24 119(4) . . ? F2 P1 F5 178.5(2) . . ? F2 P1 F4 88.67(19) . . ? F5 P1 F4 89.9(2) . . ? F2 P1 F3 89.31(18) . . ? F5 P1 F3 91.3(2) . . ? F4 P1 F3 91.2(2) . . ? F2 P1 F1 89.7(2) . . ? F5 P1 F1 91.7(2) . . ? F4 P1 F1 177.8(2) . . ? F3 P1 F1 90.2(2) . . ? F2 P1 F6 91.93(17) . . ? F5 P1 F6 87.46(19) . . ? F4 P1 F6 88.92(17) . . ? F3 P1 F6 178.8(2) . . ? F1 P1 F6 89.65(17) . . ? F11A P2 F10A 95.6(9) . . ? F9B P2 F10A 64.8(9) . . ? F9B P2 F12B 94.5(9) . . ? F11A P2 F7 94.1(7) . . ? F9B P2 F7 94.0(7) . . ? F10A P2 F7 88.8(7) . . ? F12B P2 F7 92.6(7) . . ? F11A P2 F12A 90.4(9) . . ? F10A P2 F12A 173.6(8) . . ? F7 P2 F12A 88.8(6) . . ? F11A P2 F8 85.4(7) . . ? F9B P2 F8 86.8(7) . . ? F10A P2 F8 92.2(7) . . ? F12B P2 F8 86.6(7) . . ? F7 P2 F8 178.96(18) . . ? F12A P2 F8 90.3(6) . . ? F9B P2 F10B 91.6(8) . . ? F12B P2 F10B 172.8(8) . . ? F7 P2 F10B 90.8(5) . . ? F8 P2 F10B 89.8(5) . . ? F9B P2 F11B 176.4(8) . . ? F12B P2 F11B 87.9(8) . . ? F7 P2 F11B 88.6(5) . . ? F8 P2 F11B 90.7(5) . . ? F10B P2 F11B 85.8(7) . . ? F11A P2 F9A 175.9(9) . . ? F10A P2 F9A 88.4(8) . . ? F7 P2 F9A 85.7(6) . . ? F12A P2 F9A 85.5(8) . . ? F8 P2 F9A 94.8(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 N2 Os1 S1 O1 68.54(18) . . . . ? N1 Os1 S1 O1 -108.60(18) . . . . ? N3 Os1 S1 O1 -9.76(18) . . . . ? N4 Os1 S1 O1 167.11(18) . . . . ? N2 Os1 S1 O2 -63.71(14) . . . . ? N1 Os1 S1 O2 119.16(15) . . . . ? N3 Os1 S1 O2 -142.01(14) . . . . ? N4 Os1 S1 O2 34.86(15) . . . . ? N2 Os1 S1 C1 -177.14(19) . . . . ? N1 Os1 S1 C1 5.73(19) . . . . ? N3 Os1 S1 C1 104.56(19) . . . . ? N4 Os1 S1 C1 -78.57(19) . . . . ? N3 Os1 N1 C2 -99.7(3) . . . . ? N4 Os1 N1 C2 90.4(3) . . . . ? N5 Os1 N1 C2 167.6(3) . . . . ? S1 Os1 N1 C2 -10.2(3) . . . . ? O1 S1 C1 C2 118.5(4) . . . . ? O2 S1 C1 C2 -127.0(3) . . . . ? Os1 S1 C1 C2 -2.8(4) . . . . ? Os1 N1 C2 C1 11.3(6) . . . . ? S1 C1 C2 N1 -4.7(6) . . . . ? N3 Os1 N2 C3 171.5(3) . . . . ? N4 Os1 N2 C3 -18.7(3) . . . . ? N5 Os1 N2 C3 -96.1(3) . . . . ? S1 Os1 N2 C3 81.9(3) . . . . ? N3 Os1 N2 C7 -6.6(2) . . . . ? N4 Os1 N2 C7 163.1(2) . . . . ? N5 Os1 N2 C7 85.8(2) . . . . ? S1 Os1 N2 C7 -96.3(2) . . . . ? C7 N2 C3 C4 -0.6(5) . . . . ? Os1 N2 C3 C4 -178.6(3) . . . . ? N2 C3 C4 C5 -1.0(6) . . . . ? C3 C4 C5 C6 1.5(6) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? C3 N2 C7 C6 1.5(5) . . . . ? Os1 N2 C7 C6 179.8(3) . . . . ? C3 N2 C7 C8 -174.8(3) . . . . ? Os1 N2 C7 C8 3.5(3) . . . . ? C5 C6 C7 N2 -0.9(5) . . . . ? C5 C6 C7 C8 174.9(3) . . . . ? N2 C7 C8 N3 4.1(4) . . . . ? C6 C7 C8 N3 -172.1(3) . . . . ? N2 C7 C8 C9 -177.5(3) . . . . ? C6 C7 C8 C9 6.4(5) . . . . ? N3 C8 C9 C10 1.2(5) . . . . ? C7 C8 C9 C10 -177.1(3) . . . . ? C8 C9 C10 C11 1.3(5) . . . . ? C9 C10 C11 C12 -2.0(5) . . . . ? C10 C11 C12 N3 0.2(5) . . . . ? C11 C12 N3 C8 2.4(5) . . . . ? C11 C12 N3 Os1 -172.0(3) . . . . ? C9 C8 N3 C12 -3.1(5) . . . . ? C7 C8 N3 C12 175.4(3) . . . . ? C9 C8 N3 Os1 171.9(2) . . . . ? C7 C8 N3 Os1 -9.6(3) . . . . ? N2 Os1 N3 C12 -176.7(3) . . . . ? N1 Os1 N3 C12 0.7(3) . . . . ? N4 Os1 N3 C12 114.4(5) . . . . ? N5 Os1 N3 C12 93.7(3) . . . . ? S1 Os1 N3 C12 -82.0(3) . . . . ? N2 Os1 N3 C8 8.8(2) . . . . ? N1 Os1 N3 C8 -173.8(2) . . . . ? N4 Os1 N3 C8 -60.1(6) . . . . ? N5 Os1 N3 C8 -80.8(2) . . . . ? S1 Os1 N3 C8 103.5(2) . . . . ? N2 Os1 N4 C13 90.4(3) . . . . ? N1 Os1 N4 C13 -87.5(3) . . . . ? N3 Os1 N4 C13 157.6(5) . . . . ? N5 Os1 N4 C13 178.8(3) . . . . ? S1 Os1 N4 C13 -5.7(3) . . . . ? N2 Os1 N4 C17 -93.2(2) . . . . ? N1 Os1 N4 C17 88.8(2) . . . . ? N3 Os1 N4 C17 -26.1(7) . . . . ? N5 Os1 N4 C17 -4.8(2) . . . . ? S1 Os1 N4 C17 170.6(2) . . . . ? C17 N4 C13 C14 -1.9(5) . . . . ? Os1 N4 C13 C14 174.4(3) . . . . ? N4 C13 C14 C15 -0.8(6) . . . . ? C13 C14 C15 C16 2.9(5) . . . . ? C14 C15 C16 C17 -2.2(5) . . . . ? C13 N4 C17 C16 2.6(5) . . . . ? Os1 N4 C17 C16 -174.1(2) . . . . ? C13 N4 C17 C18 -176.1(3) . . . . ? Os1 N4 C17 C18 7.2(4) . . . . ? C15 C16 C17 N4 -0.6(5) . . . . ? C15 C16 C17 C18 178.0(3) . . . . ? N4 C17 C18 N5 -5.8(4) . . . . ? C16 C17 C18 N5 175.6(3) . . . . ? N4 C17 C18 C19 170.6(3) . . . . ? C16 C17 C18 C19 -8.0(5) . . . . ? N5 C18 C19 C20 -0.9(5) . . . . ? C17 C18 C19 C20 -177.1(3) . . . . ? C18 C19 C20 C21 -1.0(6) . . . . ? C19 C20 C21 C22 1.3(6) . . . . ? C20 C21 C22 N5 0.2(6) . . . . ? C21 C22 N5 C18 -2.0(5) . . . . ? C21 C22 N5 Os1 174.9(3) . . . . ? C19 C18 N5 C22 2.4(5) . . . . ? C17 C18 N5 C22 178.8(3) . . . . ? C19 C18 N5 Os1 -174.8(3) . . . . ? C17 C18 N5 Os1 1.6(4) . . . . ? N2 Os1 N5 C22 -77.6(3) . . . . ? N1 Os1 N5 C22 99.6(3) . . . . ? N3 Os1 N5 C22 0.7(3) . . . . ? N4 Os1 N5 C22 -175.4(3) . . . . ? N2 Os1 N5 C18 99.4(2) . . . . ? N1 Os1 N5 C18 -83.4(2) . . . . ? N3 Os1 N5 C18 177.6(2) . . . . ? N4 Os1 N5 C18 1.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 F11B 0.74(4) 2.39(5) 3.121(14) 173(4) 2 N1 H1 F12A 0.74(4) 2.54(4) 3.089(13) 133(4) 2 N6 H21 F3 0.95(4) 2.03(4) 2.813(5) 139(4) 1_565 N6 H22 O2 0.90(4) 1.80(4) 2.700(4) 175(4) . N6 H23 O1 0.99(4) 1.75(4) 2.712(4) 165(4) 3_675 N6 H23 S1 0.99(4) 2.95(4) 3.916(3) 167(3) 3_675 N6 H24 F6 0.87(4) 2.15(4) 2.994(5) 164(4) 2_655 N6 H24 F1 0.87(4) 2.35(5) 3.021(5) 134(4) 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.611 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.109 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. ;