# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Kathryn Preuss' _publ_contact_author_address ; 0 Stone Road E. Guelph Ontario Canada N1G 2W1 ; _publ_contact_author_email kpreuss@uoguelph.ca loop_ _publ_author_name K.Preuss E.Fatila J.Goodreid R.Clerac M.Jennings J.Assoud data_b09011_0m _database_code_depnum_ccdc_archive 'CCDC 774618' #TrackingRef 'B09011-0m-OK.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H4 N2 O' _chemical_formula_sum 'C8 H4 N2 O' _chemical_formula_weight 144.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0278(3) _cell_length_b 7.2916(4) _cell_length_c 7.6914(4) _cell_angle_alpha 117.269(4) _cell_angle_beta 90.138(4) _cell_angle_gamma 106.131(4) _cell_volume 332.64(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1978 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.22 _exptl_crystal_description cut _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 148 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9411 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details SADBAS _exptl_special_details ; disorder modelled at 50/50 iso for O and N EADP O4a N4b EADP N11a O11b SADI C3 N4b C3 N11a SADI C5 N4b C10 N11a SADI C3 o4a c3 O11b SADI C5 O4a C10 O11b ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4938 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1352 _reflns_number_gt 1076 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.1191P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1352 _refine_ls_number_parameters 96 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.088 _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 N1 N 0.4673(2) 0.2533(3) 0.0296(2) 0.0459(4) Uani 1 1 d . . . C2 C 0.3579(2) 0.2530(3) 0.1397(3) 0.0341(4) Uani 1 1 d . A . C3 C 0.2219(3) 0.2525(3) 0.2778(3) 0.0335(4) Uani 1 1 d D . . O4A O 0.2896(7) 0.2965(7) 0.4679(6) 0.0273(4) Uiso 0.50 1 d PD A 1 N11A N 0.0344(10) 0.2258(11) 0.2441(10) 0.0305(4) Uiso 0.50 1 d PD A 1 N4B N 0.2800(9) 0.2802(9) 0.4413(8) 0.0273(4) Uiso 0.50 1 d PD A 2 O11B O 0.0228(8) 0.2066(9) 0.2254(8) 0.0305(4) Uiso 0.50 1 d PD A 2 C5 C 0.1110(2) 0.2741(2) 0.5420(2) 0.0265(4) Uani 1 1 d D . . C6 C 0.0844(2) 0.2950(2) 0.7275(2) 0.0315(4) Uani 1 1 d . A . H6 H 0.1930 0.3249 0.8205 0.038 Uiso 1 1 calc R . . C7 C -0.1102(2) 0.2696(2) 0.7702(2) 0.0321(4) Uani 1 1 d . . . H7 H -0.1361 0.2818 0.8955 0.039 Uiso 1 1 calc R A . C8 C -0.2693(2) 0.2265(2) 0.6323(2) 0.0316(4) Uani 1 1 d . A . H8 H -0.4001 0.2114 0.6674 0.038 Uiso 1 1 calc R . . C9 C -0.2417(2) 0.2051(3) 0.4472(3) 0.0305(4) Uani 1 1 d . . . H9 H -0.3497 0.1757 0.3540 0.037 Uiso 1 1 calc R A . C10 C -0.0464(2) 0.2292(2) 0.4048(2) 0.0268(4) Uani 1 1 d D A . 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 N1 0.0402(9) 0.0574(11) 0.0421(9) 0.0256(8) 0.0115(8) 0.0147(8) C2 0.0309(9) 0.0387(9) 0.0363(10) 0.0197(8) 0.0048(8) 0.0131(7) C3 0.0332(9) 0.0313(9) 0.0417(10) 0.0194(8) 0.0136(7) 0.0148(7) C5 0.0245(8) 0.0213(7) 0.0333(9) 0.0117(6) 0.0056(6) 0.0088(6) C6 0.0319(8) 0.0277(8) 0.0321(9) 0.0124(7) -0.0007(7) 0.0089(6) C7 0.0359(9) 0.0263(8) 0.0305(9) 0.0108(7) 0.0073(7) 0.0095(7) C8 0.0252(8) 0.0278(8) 0.0385(10) 0.0126(7) 0.0090(7) 0.0092(6) C9 0.0234(8) 0.0286(8) 0.0380(9) 0.0135(7) 0.0012(7) 0.0100(6) C10 0.0278(8) 0.0218(8) 0.0308(9) 0.0114(6) 0.0046(7) 0.0097(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 N1 C2 1.146(2) . ? C2 C3 1.431(2) . ? C3 N4B 1.228(6) . ? C3 N11A 1.285(7) . ? C3 O11B 1.358(6) . ? C3 O4A 1.397(5) . ? O4A C5 1.379(5) . ? N11A C10 1.354(7) . ? N4B C5 1.420(6) . ? O11B C10 1.416(6) . ? C5 C6 1.383(2) . ? C5 C10 1.386(2) . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C8 1.402(2) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.394(2) . ? C9 H9 0.9500 . ? 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 C3 179.72(19) . . ? N4B C3 N11A 115.0(5) . . ? N4B C3 O11B 118.4(4) . . ? N11A C3 O4A 114.8(4) . . ? O11B C3 O4A 118.5(3) . . ? N4B C3 C2 121.0(3) . . ? N11A C3 C2 124.0(4) . . ? O11B C3 C2 120.5(3) . . ? O4A C3 C2 121.1(2) . . ? C5 O4A C3 100.3(3) . . ? C3 N11A C10 107.3(5) . . ? C3 N4B C5 106.9(4) . . ? C3 O11B C10 100.0(4) . . ? O4A C5 C6 126.7(2) . . ? O4A C5 C10 110.9(2) . . ? C6 C5 C10 122.42(14) . . ? C6 C5 N4B 133.3(3) . . ? C10 C5 N4B 104.2(3) . . ? C5 C6 C7 116.16(15) . . ? C5 C6 H6 121.9 . . ? C7 C6 H6 121.9 . . ? C6 C7 C8 121.49(16) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 122.01(15) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 116.24(15) . . ? C8 C9 H9 121.9 . . ? C10 C9 H9 121.9 . . ? N11A C10 C5 106.4(3) . . ? N11A C10 C9 131.9(3) . . ? C5 C10 C9 121.68(15) . . ? C5 C10 O11B 110.1(3) . . ? C9 C10 O11B 128.1(3) . . ? 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 N4B C3 O4A C5 -90(8) . . . . ? N11A C3 O4A C5 5.0(5) . . . . ? O11B C3 O4A C5 0.3(5) . . . . ? C2 C3 O4A C5 -178.96(19) . . . . ? N4B C3 N11A C10 -2.1(7) . . . . ? O11B C3 N11A C10 127(6) . . . . ? O4A C3 N11A C10 -5.7(6) . . . . ? C2 C3 N11A C10 178.4(2) . . . . ? N11A C3 N4B C5 -0.4(6) . . . . ? O11B C3 N4B C5 -5.4(6) . . . . ? O4A C3 N4B C5 87(8) . . . . ? C2 C3 N4B C5 179.1(2) . . . . ? N4B C3 O11B C10 5.4(5) . . . . ? N11A C3 O11B C10 -48(6) . . . . ? O4A C3 O11B C10 1.7(5) . . . . ? C2 C3 O11B C10 -179.0(2) . . . . ? C3 O4A C5 C6 178.53(17) . . . . ? C3 O4A C5 C10 -2.3(3) . . . . ? C3 O4A C5 N4B 22(3) . . . . ? C3 N4B C5 O4A -153(4) . . . . ? C3 N4B C5 C6 180.0(2) . . . . ? C3 N4B C5 C10 2.7(4) . . . . ? O4A C5 C6 C7 178.7(3) . . . . ? C10 C5 C6 C7 -0.4(2) . . . . ? N4B C5 C6 C7 -177.2(3) . . . . ? C5 C6 C7 C8 -0.3(2) . . . . ? C6 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C3 N11A C10 C5 3.7(5) . . . . ? C3 N11A C10 C9 -179.0(2) . . . . ? C3 N11A C10 O11B -130(6) . . . . ? O4A C5 C10 N11A -0.7(4) . . . . ? C6 C5 C10 N11A 178.5(3) . . . . ? N4B C5 C10 N11A -3.9(4) . . . . ? O4A C5 C10 C9 -178.3(2) . . . . ? C6 C5 C10 C9 0.9(2) . . . . ? N4B C5 C10 C9 178.5(3) . . . . ? O4A C5 C10 O11B 3.6(4) . . . . ? C6 C5 C10 O11B -177.2(3) . . . . ? N4B C5 C10 O11B 0.5(4) . . . . ? C8 C9 C10 N11A -177.6(4) . . . . ? C8 C9 C10 C5 -0.6(2) . . . . ? C8 C9 C10 O11B 177.1(3) . . . . ? C3 O11B C10 N11A 45(6) . . . . ? C3 O11B C10 C5 -3.1(4) . . . . ? C3 O11B C10 C9 179.03(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.209 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.044 # Attachment 'EF-4-41-subl-0m-march2010.cif.txt' data_ef_4_41_subl_0m _database_code_depnum_ccdc_archive 'CCDC 774619' #TrackingRef 'EF-4-41-subl-0m-march2010.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H6 F12 Mn N3 O5 S2' _chemical_formula_sum 'C18 H6 F12 Mn N3 O5 S2' _chemical_formula_weight 691.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.999(5) _cell_length_b 18.698(8) _cell_length_c 12.089(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.635(6) _cell_angle_gamma 90.00 _cell_volume 2469.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8665 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 25.93 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8005 _exptl_absorpt_correction_T_max 0.9215 _exptl_absorpt_process_details 'APEX II' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23409 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8558 _reflns_number_gt 7593 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+2.1768P] 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 SHELXL _refine_ls_extinction_coef 0.0012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), 4089 Friedel pairs, Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(2) _refine_ls_number_reflns 8558 _refine_ls_number_parameters 741 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Mn1 Mn -0.05558(6) 0.32753(4) -0.12079(6) 0.03342(19) Uani 1 1 d . . . N1 N 0.0663(4) 0.2267(2) -0.0746(4) 0.0395(10) Uani 1 1 d . . . S2 S 0.21062(13) 0.22142(9) -0.02245(13) 0.0531(4) Uani 1 1 d . . . S3 S 0.22177(14) 0.11212(10) -0.05733(15) 0.0589(4) Uani 1 1 d . . . N4 N 0.0798(4) 0.1041(3) -0.1111(4) 0.0469(11) Uani 1 1 d . . . C5 C 0.0185(5) 0.1647(3) -0.1130(4) 0.0386(12) Uani 1 1 d . . . C6 C -0.1108(5) 0.1692(3) -0.1600(4) 0.0390(12) Uani 1 1 d . . . O7 O -0.1739(3) 0.1095(2) -0.1901(3) 0.0447(9) Uani 1 1 d . . . C8 C -0.2904(5) 0.1355(3) -0.2290(4) 0.0416(12) Uani 1 1 d . . . C9 C -0.3918(6) 0.0963(4) -0.2705(6) 0.0586(17) Uani 1 1 d . . . H9A H -0.3915 0.0456 -0.2757 0.070 Uiso 1 1 calc R . . C10 C -0.4948(6) 0.1378(4) -0.3043(6) 0.0635(18) Uani 1 1 d . . . H10A H -0.5680 0.1147 -0.3347 0.076 Uiso 1 1 calc R . . C11 C -0.4937(5) 0.2107(4) -0.2949(5) 0.0579(16) Uani 1 1 d . . . H11A H -0.5668 0.2360 -0.3193 0.069 Uiso 1 1 calc R . . C12 C -0.3925(5) 0.2494(4) -0.2521(5) 0.0470(14) Uani 1 1 d . . . H12A H -0.3938 0.3000 -0.2454 0.056 Uiso 1 1 calc R . . C13 C -0.2883(4) 0.2091(3) -0.2192(4) 0.0359(11) Uani 1 1 d . . . N14 N -0.1694(4) 0.2288(2) -0.1735(3) 0.0326(10) Uani 1 1 d . . . O21 O -0.1328(3) 0.3476(2) 0.0339(3) 0.0420(9) Uani 1 1 d . . . C22 C -0.2273(5) 0.3829(3) 0.0469(4) 0.0415(13) Uani 1 1 d . . . C23 C -0.2998(5) 0.4225(3) -0.0305(4) 0.0416(12) Uani 1 1 d . . . H23A H -0.3707 0.4450 -0.0085 0.050 Uiso 1 1 calc R . . C24 C -0.2736(4) 0.4312(3) -0.1415(4) 0.0348(11) Uani 1 1 d . . . O25 O -0.1915(3) 0.4009(2) -0.1867(3) 0.0414(9) Uani 1 1 d . . . C26 C -0.2659(6) 0.3811(4) 0.1644(5) 0.0564(17) Uani 1 1 d . . . C27 C -0.3585(5) 0.4799(3) -0.2165(5) 0.0461(13) Uani 1 1 d . . . F21 F -0.2075(6) 0.4295(5) 0.2250(4) 0.148(3) Uani 1 1 d . . . F22 F -0.3804(4) 0.3869(4) 0.1702(3) 0.106(2) Uani 1 1 d . . . F23 F -0.2342(6) 0.3216(4) 0.2161(4) 0.143(3) Uani 1 1 d . . . F24 F -0.4084(4) 0.5310(2) -0.1618(3) 0.0742(11) Uani 1 1 d . . . F25 F -0.2989(3) 0.5104(2) -0.2939(3) 0.0600(9) Uani 1 1 d . . . F26 F -0.4492(3) 0.4413(2) -0.2702(3) 0.0687(11) Uani 1 1 d . . . O31 O 0.1036(3) 0.3858(2) -0.0597(3) 0.0430(9) Uani 1 1 d . . . C32 C 0.1956(5) 0.4013(3) -0.1082(4) 0.0411(12) Uani 1 1 d . . . C33 C 0.2135(5) 0.3895(3) -0.2180(4) 0.0460(14) Uani 1 1 d . . . H33A H 0.2903 0.4015 -0.2419 0.055 Uiso 1 1 calc R . . C34 C 0.1227(4) 0.3607(3) -0.2947(4) 0.0355(11) Uani 1 1 d . . . O35 O 0.0196(3) 0.3367(2) -0.2775(3) 0.0412(8) Uani 1 1 d . . . C36 C 0.2973(6) 0.4402(5) -0.0325(5) 0.067(2) Uani 1 1 d . . . C37 C 0.1455(5) 0.3617(4) -0.4177(5) 0.0537(16) Uani 1 1 d . . . F31 F 0.2525(5) 0.4977(3) 0.0136(5) 0.116(2) Uani 1 1 d . . . F32 F 0.3898(5) 0.4573(5) -0.0795(4) 0.153(3) Uani 1 1 d . . . F33 F 0.3341(4) 0.3982(4) 0.0550(4) 0.1036(19) Uani 1 1 d . . . F34 F 0.1051(4) 0.4229(2) -0.4646(3) 0.0728(11) Uani 1 1 d . . . F35 F 0.2625(3) 0.3561(3) -0.4314(3) 0.0844(15) Uani 1 1 d . . . F36 F 0.0851(3) 0.3109(2) -0.4765(3) 0.0646(10) Uani 1 1 d . . . Mn2 Mn 0.33751(6) 0.20801(4) 0.32703(6) 0.03511(19) Uani 1 1 d . . . N41 N 0.2200(4) 0.3097(3) 0.2740(3) 0.0378(10) Uani 1 1 d . . . S42 S 0.07993(13) 0.31616(9) 0.21001(12) 0.0507(4) Uani 1 1 d . . . S43 S 0.08061(15) 0.42794(9) 0.21626(14) 0.0585(4) Uani 1 1 d . . . N44 N 0.2200(4) 0.4345(3) 0.2794(4) 0.0505(12) Uani 1 1 d . . . C45 C 0.2733(5) 0.3727(3) 0.2991(4) 0.0366(11) Uani 1 1 d . . . C46 C 0.3979(5) 0.3675(3) 0.3554(4) 0.0367(11) Uani 1 1 d . . . O47 O 0.4655(3) 0.4263(2) 0.3773(3) 0.0455(9) Uani 1 1 d . . . C48 C 0.5759(5) 0.3996(3) 0.4298(4) 0.0429(13) Uani 1 1 d . . . C49 C 0.6780(6) 0.4388(4) 0.4707(5) 0.0573(16) Uani 1 1 d . . . H49A H 0.6813 0.4895 0.4658 0.069 Uiso 1 1 calc R . . C50 C 0.7747(6) 0.3981(4) 0.5191(5) 0.0624(19) Uani 1 1 d . . . H50A H 0.8474 0.4218 0.5495 0.075 Uiso 1 1 calc R . . C51 C 0.7698(5) 0.3235(5) 0.5253(5) 0.0584(16) Uani 1 1 d . . . H51A H 0.8393 0.2978 0.5581 0.070 Uiso 1 1 calc R . . C52 C 0.6661(5) 0.2870(4) 0.4848(4) 0.0458(13) Uani 1 1 d . . . H52A H 0.6618 0.2363 0.4896 0.055 Uiso 1 1 calc R . . C53 C 0.5676(4) 0.3270(3) 0.4362(4) 0.0355(11) Uani 1 1 d . . . N54 N 0.4505(4) 0.3070(3) 0.3862(3) 0.0384(11) Uani 1 1 d . . . O61 O 0.4820(3) 0.1371(2) 0.3861(3) 0.0417(9) Uani 1 1 d . . . C62 C 0.5765(4) 0.1214(3) 0.3430(4) 0.0348(11) Uani 1 1 d . . . C63 C 0.6088(4) 0.1444(3) 0.2402(4) 0.0385(12) Uani 1 1 d . . . H63A H 0.6884 0.1338 0.2216 0.046 Uiso 1 1 calc R . . C64 C 0.5288(4) 0.1819(3) 0.1647(4) 0.0363(11) Uani 1 1 d . . . O65 O 0.4245(3) 0.2054(2) 0.1758(3) 0.0400(8) Uani 1 1 d . . . C66 C 0.6665(5) 0.0722(3) 0.4130(5) 0.0465(13) Uani 1 1 d . . . C67 C 0.5660(5) 0.1946(4) 0.0482(4) 0.0507(15) Uani 1 1 d . . . F61 F 0.7311(6) 0.0331(4) 0.3542(4) 0.135(3) Uani 1 1 d . . . F62 F 0.6102(4) 0.0279(3) 0.4720(4) 0.1014(18) Uani 1 1 d . . . F63 F 0.7416(5) 0.1081(3) 0.4822(6) 0.135(3) Uani 1 1 d . . . F64 F 0.5022(4) 0.1518(3) -0.0239(3) 0.0865(15) Uani 1 1 d . . . F65 F 0.6831(3) 0.1827(4) 0.0408(3) 0.104(2) Uani 1 1 d . . . F66 F 0.5416(5) 0.2597(3) 0.0124(4) 0.1024(18) Uani 1 1 d . . . O71 O 0.2534(3) 0.1819(2) 0.4735(3) 0.0450(9) Uani 1 1 d . . . C72 C 0.1554(5) 0.1481(3) 0.4802(4) 0.0403(12) Uani 1 1 d . . . C73 C 0.0761(5) 0.1194(4) 0.3950(5) 0.0495(14) Uani 1 1 d . . . H73A H 0.0041 0.0963 0.4135 0.059 Uiso 1 1 calc R . . C74 C 0.0957(4) 0.1224(3) 0.2835(4) 0.0416(12) Uani 1 1 d . . . O75 O 0.1826(3) 0.1524(2) 0.2436(3) 0.0401(8) Uani 1 1 d . . . C76 C 0.1231(6) 0.1398(4) 0.5994(5) 0.0547(15) Uani 1 1 d . . . C77 C 0.0019(5) 0.0880(4) 0.1959(6) 0.0562(16) Uani 1 1 d . . . F71 F 0.1584(7) 0.0757(3) 0.6370(4) 0.129(3) Uani 1 1 d . . . F72 F 0.0070(4) 0.1473(4) 0.6082(3) 0.1024(19) Uani 1 1 d . . . F73 F 0.1801(4) 0.1846(3) 0.6712(3) 0.0822(14) Uani 1 1 d . . . F74 F 0.0555(4) 0.0476(3) 0.1267(3) 0.0826(14) Uani 1 1 d . . . F75 F -0.0794(6) 0.0500(4) 0.2364(4) 0.152(3) Uani 1 1 d . . . F76 F -0.0560(5) 0.1384(3) 0.1324(5) 0.112(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0254(4) 0.0432(4) 0.0319(4) 0.0004(3) 0.0041(3) 0.0017(3) N1 0.038(2) 0.040(3) 0.038(2) 0.0044(19) -0.0034(18) 0.005(2) S2 0.0363(7) 0.0616(10) 0.0576(9) 0.0069(7) -0.0110(6) 0.0041(7) S3 0.0447(8) 0.0603(10) 0.0695(10) 0.0118(8) -0.0023(7) 0.0162(7) N4 0.046(3) 0.048(3) 0.047(3) 0.006(2) 0.004(2) 0.009(2) C5 0.038(3) 0.050(3) 0.028(2) 0.002(2) 0.006(2) 0.006(2) C6 0.036(3) 0.055(3) 0.026(2) -0.003(2) 0.0045(19) -0.002(3) O7 0.045(2) 0.042(2) 0.046(2) -0.0039(17) -0.0014(16) -0.0012(17) C8 0.037(3) 0.053(3) 0.034(3) -0.005(2) 0.000(2) -0.004(2) C9 0.056(4) 0.049(4) 0.068(4) -0.013(3) -0.005(3) -0.008(3) C10 0.038(3) 0.081(5) 0.069(4) -0.021(4) -0.008(3) -0.016(3) C11 0.038(3) 0.075(5) 0.059(4) 0.002(3) -0.002(3) 0.003(3) C12 0.035(3) 0.059(4) 0.046(3) 0.006(3) -0.001(2) 0.006(3) C13 0.037(3) 0.041(3) 0.029(2) 0.002(2) 0.0021(19) -0.004(2) N14 0.029(2) 0.038(3) 0.031(2) 0.0023(17) 0.0009(17) 0.0016(17) O21 0.0355(19) 0.056(2) 0.0348(18) 0.0056(16) 0.0048(14) 0.0072(17) C22 0.033(3) 0.059(4) 0.032(3) -0.002(2) 0.005(2) -0.007(2) C23 0.034(3) 0.050(3) 0.042(3) -0.001(2) 0.008(2) 0.007(2) C24 0.031(2) 0.038(3) 0.035(2) 0.001(2) 0.0030(19) -0.006(2) O25 0.040(2) 0.049(2) 0.036(2) 0.0046(16) 0.0089(15) 0.0122(17) C26 0.046(3) 0.087(5) 0.037(3) 0.001(3) 0.010(2) 0.005(3) C27 0.038(3) 0.052(4) 0.048(3) 0.003(3) 0.000(2) 0.009(3) F21 0.154(5) 0.235(8) 0.064(3) -0.076(4) 0.048(3) -0.100(6) F22 0.046(2) 0.219(7) 0.058(2) 0.009(3) 0.0254(18) 0.012(3) F23 0.169(6) 0.199(7) 0.074(3) 0.072(4) 0.070(3) 0.084(6) F24 0.078(3) 0.071(3) 0.073(3) 0.001(2) 0.005(2) 0.041(2) F25 0.062(2) 0.057(2) 0.060(2) 0.0221(18) 0.0033(17) 0.0047(17) F26 0.053(2) 0.066(3) 0.079(3) 0.014(2) -0.0236(18) -0.0036(19) O31 0.0351(19) 0.061(3) 0.0330(18) -0.0033(17) 0.0071(15) -0.0110(18) C32 0.036(3) 0.050(3) 0.037(3) 0.002(2) 0.001(2) -0.006(2) C33 0.033(3) 0.065(4) 0.041(3) -0.001(3) 0.010(2) -0.004(3) C34 0.035(3) 0.042(3) 0.030(2) 0.005(2) 0.0044(19) 0.003(2) O35 0.0332(18) 0.057(2) 0.0343(17) -0.0023(17) 0.0072(14) -0.0061(17) C36 0.061(4) 0.101(6) 0.040(3) -0.010(4) 0.012(3) -0.030(4) C37 0.046(3) 0.083(5) 0.033(3) 0.002(3) 0.008(2) -0.003(3) F31 0.104(4) 0.117(5) 0.123(4) -0.054(4) -0.012(3) -0.036(3) F32 0.079(3) 0.298(10) 0.083(3) -0.039(4) 0.015(3) -0.114(5) F33 0.075(3) 0.170(6) 0.059(3) 0.005(3) -0.025(2) -0.013(3) F34 0.096(3) 0.080(3) 0.0418(19) 0.0168(19) 0.0079(18) -0.001(2) F35 0.055(2) 0.154(5) 0.049(2) -0.014(2) 0.0276(17) -0.003(3) F36 0.073(2) 0.080(3) 0.0434(18) -0.0203(19) 0.0151(16) -0.008(2) Mn2 0.0274(4) 0.0446(5) 0.0336(4) 0.0011(3) 0.0047(3) 0.0007(3) N41 0.032(2) 0.044(3) 0.036(2) 0.0018(19) 0.0008(17) 0.0005(19) S42 0.0363(7) 0.0593(10) 0.0531(8) 0.0021(7) -0.0085(6) 0.0059(7) S43 0.0497(9) 0.0553(10) 0.0666(10) 0.0037(8) -0.0091(7) 0.0169(7) N44 0.047(3) 0.059(3) 0.044(3) 0.000(2) 0.000(2) 0.010(3) C45 0.039(3) 0.040(3) 0.031(3) 0.002(2) 0.006(2) 0.007(2) C46 0.035(3) 0.046(3) 0.029(2) -0.006(2) 0.003(2) -0.004(2) O47 0.048(2) 0.049(2) 0.039(2) -0.0040(17) 0.0008(16) -0.0042(18) C48 0.047(3) 0.049(3) 0.032(3) -0.004(2) 0.001(2) -0.004(3) C49 0.060(4) 0.064(4) 0.046(3) -0.007(3) 0.000(3) -0.023(3) C50 0.047(4) 0.091(6) 0.047(3) -0.005(3) -0.004(3) -0.021(4) C51 0.043(3) 0.080(5) 0.048(3) -0.002(3) -0.008(2) 0.000(3) C52 0.040(3) 0.053(3) 0.042(3) -0.005(3) -0.005(2) 0.001(3) C53 0.036(3) 0.042(3) 0.028(2) -0.004(2) 0.0042(18) -0.009(2) N54 0.030(2) 0.052(3) 0.032(2) -0.0028(19) -0.0001(17) 0.0006(19) O61 0.0335(18) 0.059(2) 0.0343(18) 0.0066(17) 0.0087(14) 0.0059(18) C62 0.029(2) 0.041(3) 0.034(2) 0.000(2) 0.0024(19) 0.000(2) C63 0.026(2) 0.051(3) 0.038(3) 0.003(2) 0.0024(19) -0.003(2) C64 0.032(3) 0.042(3) 0.035(3) 0.003(2) 0.0061(19) -0.010(2) O65 0.0357(18) 0.050(2) 0.0346(17) 0.0072(17) 0.0051(14) 0.0025(17) C66 0.041(3) 0.053(3) 0.046(3) 0.010(3) 0.006(2) 0.008(3) C67 0.040(3) 0.076(5) 0.036(3) 0.009(3) 0.005(2) -0.002(3) F61 0.170(5) 0.151(5) 0.093(4) 0.051(4) 0.057(4) 0.120(5) F62 0.074(3) 0.121(4) 0.110(4) 0.076(3) 0.015(2) 0.015(3) F63 0.109(4) 0.099(4) 0.171(6) 0.020(4) -0.098(4) 0.006(3) F64 0.093(3) 0.124(4) 0.044(2) -0.023(2) 0.015(2) -0.035(3) F65 0.043(2) 0.219(7) 0.053(2) 0.029(3) 0.0206(16) 0.002(3) F66 0.147(5) 0.096(4) 0.074(3) 0.046(3) 0.052(3) 0.022(3) O71 0.0336(19) 0.069(3) 0.0333(18) 0.0009(17) 0.0071(14) -0.0014(18) C72 0.035(3) 0.045(3) 0.043(3) 0.003(2) 0.013(2) 0.008(2) C73 0.036(3) 0.067(4) 0.048(3) 0.003(3) 0.015(2) -0.011(3) C74 0.029(3) 0.051(3) 0.045(3) -0.004(3) 0.007(2) 0.000(2) O75 0.0334(18) 0.050(2) 0.0381(19) 0.0014(16) 0.0080(14) -0.0078(16) C76 0.050(3) 0.070(4) 0.046(3) 0.007(3) 0.014(3) 0.001(3) C77 0.041(3) 0.067(4) 0.061(4) -0.008(3) 0.008(3) -0.014(3) F71 0.251(8) 0.078(3) 0.070(3) 0.034(3) 0.073(4) 0.049(4) F72 0.052(2) 0.201(6) 0.059(2) -0.010(3) 0.0289(19) -0.005(3) F73 0.092(3) 0.115(4) 0.041(2) -0.005(2) 0.0164(19) -0.016(3) F74 0.074(3) 0.103(4) 0.069(3) -0.032(2) 0.001(2) -0.011(2) F75 0.140(5) 0.240(8) 0.083(3) -0.046(4) 0.039(3) -0.147(6) F76 0.084(3) 0.113(4) 0.123(4) -0.022(3) -0.054(3) 0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O25 2.116(4) . ? Mn1 O31 2.121(4) . ? Mn1 O35 2.160(3) . ? Mn1 O21 2.174(4) . ? Mn1 N14 2.280(4) . ? Mn1 N1 2.343(5) . ? N1 C5 1.334(8) . ? N1 S2 1.642(4) . ? S2 S3 2.093(3) . ? S3 N4 1.628(5) . ? N4 C5 1.318(8) . ? C5 C6 1.472(8) . ? C6 N14 1.288(7) . ? C6 O7 1.343(7) . ? O7 C8 1.399(7) . ? C8 C9 1.380(8) . ? C8 C13 1.381(8) . ? C9 C10 1.395(10) . ? C9 H9A 0.9500 . ? C10 C11 1.367(11) . ? C10 H10A 0.9500 . ? C11 C12 1.378(9) . ? C11 H11A 0.9500 . ? C12 C13 1.391(8) . ? C12 H12A 0.9500 . ? C13 N14 1.408(6) . ? O21 C22 1.257(6) . ? C22 C23 1.374(8) . ? C22 C26 1.528(8) . ? C23 C24 1.414(7) . ? C23 H23A 0.9500 . ? C24 O25 1.245(6) . ? C24 C27 1.526(7) . ? C26 F22 1.275(7) . ? C26 F21 1.288(9) . ? C26 F23 1.304(10) . ? C27 F24 1.317(7) . ? C27 F25 1.331(7) . ? C27 F26 1.337(7) . ? O31 C32 1.260(7) . ? C32 C33 1.383(8) . ? C32 C36 1.543(8) . ? C33 C34 1.391(7) . ? C33 H33A 0.9500 . ? C34 O35 1.259(6) . ? C34 C37 1.536(7) . ? C36 F32 1.263(8) . ? C36 F31 1.332(10) . ? C36 F33 1.342(9) . ? C37 F36 1.319(8) . ? C37 F35 1.321(7) . ? C37 F34 1.331(8) . ? Mn2 O61 2.129(4) . ? Mn2 O75 2.145(4) . ? Mn2 O71 2.146(4) . ? Mn2 O65 2.160(3) . ? Mn2 N54 2.297(5) . ? Mn2 N41 2.346(5) . ? N41 C45 1.336(8) . ? N41 S42 1.646(4) . ? S42 S43 2.091(3) . ? S43 N44 1.636(5) . ? N44 C45 1.305(8) . ? C45 C46 1.461(7) . ? C46 N54 1.306(7) . ? C46 O47 1.337(7) . ? O47 C48 1.396(7) . ? C48 C53 1.364(8) . ? C48 C49 1.383(8) . ? C49 C50 1.382(10) . ? C49 H49A 0.9500 . ? C50 C51 1.399(11) . ? C50 H50A 0.9500 . ? C51 C52 1.370(9) . ? C51 H51A 0.9500 . ? C52 C53 1.390(8) . ? C52 H52A 0.9500 . ? C53 N54 1.409(6) . ? O61 C62 1.250(6) . ? C62 C63 1.399(7) . ? C62 C66 1.534(7) . ? C63 C64 1.383(7) . ? C63 H63A 0.9500 . ? C64 O65 1.250(6) . ? C64 C67 1.530(7) . ? C66 F61 1.288(7) . ? C66 F63 1.294(8) . ? C66 F62 1.296(7) . ? C67 F66 1.309(8) . ? C67 F65 1.320(7) . ? C67 F64 1.324(8) . ? O71 C72 1.260(6) . ? C72 C73 1.379(8) . ? C72 C76 1.532(8) . ? C73 C74 1.391(8) . ? C73 H73A 0.9500 . ? C74 O75 1.252(6) . ? C74 C77 1.532(8) . ? C76 F72 1.301(7) . ? C76 F73 1.312(8) . ? C76 F71 1.324(8) . ? C77 F75 1.283(8) . ? C77 F74 1.317(8) . ? C77 F76 1.330(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O25 Mn1 O31 108.48(17) . . ? O25 Mn1 O35 86.77(14) . . ? O31 Mn1 O35 83.15(13) . . ? O25 Mn1 O21 83.27(13) . . ? O31 Mn1 O21 90.03(14) . . ? O35 Mn1 O21 165.50(16) . . ? O25 Mn1 N14 94.49(15) . . ? O31 Mn1 N14 156.62(15) . . ? O35 Mn1 N14 94.15(14) . . ? O21 Mn1 N14 97.11(15) . . ? O25 Mn1 N1 166.26(16) . . ? O31 Mn1 N1 84.47(17) . . ? O35 Mn1 N1 90.37(15) . . ? O21 Mn1 N1 101.73(15) . . ? N14 Mn1 N1 72.30(16) . . ? C5 N1 S2 113.9(4) . . ? C5 N1 Mn1 115.1(3) . . ? S2 N1 Mn1 129.9(3) . . ? N1 S2 S3 93.35(18) . . ? N4 S3 S2 95.5(2) . . ? C5 N4 S3 113.1(4) . . ? N4 C5 N1 124.2(5) . . ? N4 C5 C6 121.7(5) . . ? N1 C5 C6 114.1(5) . . ? N14 C6 O7 116.7(4) . . ? N14 C6 C5 123.1(5) . . ? O7 C6 C5 120.2(5) . . ? C6 O7 C8 103.1(4) . . ? C9 C8 C13 124.4(6) . . ? C9 C8 O7 127.4(6) . . ? C13 C8 O7 108.2(5) . . ? C8 C9 C10 114.0(6) . . ? C8 C9 H9A 123.0 . . ? C10 C9 H9A 123.0 . . ? C11 C10 C9 122.1(6) . . ? C11 C10 H10A 118.9 . . ? C9 C10 H10A 118.9 . . ? C10 C11 C12 123.6(6) . . ? C10 C11 H11A 118.2 . . ? C12 C11 H11A 118.2 . . ? C11 C12 C13 115.3(6) . . ? C11 C12 H12A 122.4 . . ? C13 C12 H12A 122.4 . . ? C8 C13 C12 120.7(5) . . ? C8 C13 N14 107.4(5) . . ? C12 C13 N14 131.9(5) . . ? C6 N14 C13 104.6(4) . . ? C6 N14 Mn1 114.5(3) . . ? C13 N14 Mn1 140.9(4) . . ? C22 O21 Mn1 127.6(3) . . ? O21 C22 C23 128.4(5) . . ? O21 C22 C26 115.3(5) . . ? C23 C22 C26 116.3(5) . . ? C22 C23 C24 122.8(5) . . ? C22 C23 H23A 118.6 . . ? C24 C23 H23A 118.6 . . ? O25 C24 C23 127.1(5) . . ? O25 C24 C27 115.8(4) . . ? C23 C24 C27 117.1(5) . . ? C24 O25 Mn1 130.3(3) . . ? F22 C26 F21 109.9(7) . . ? F22 C26 F23 104.8(6) . . ? F21 C26 F23 103.8(6) . . ? F22 C26 C22 115.6(5) . . ? F21 C26 C22 109.8(6) . . ? F23 C26 C22 112.1(6) . . ? F24 C27 F25 108.1(5) . . ? F24 C27 F26 107.7(5) . . ? F25 C27 F26 106.9(5) . . ? F24 C27 C24 113.3(5) . . ? F25 C27 C24 110.9(4) . . ? F26 C27 C24 109.7(5) . . ? C32 O31 Mn1 129.1(3) . . ? O31 C32 C33 128.5(5) . . ? O31 C32 C36 113.5(5) . . ? C33 C32 C36 118.0(5) . . ? C32 C33 C34 122.1(5) . . ? C32 C33 H33A 119.0 . . ? C34 C33 H33A 119.0 . . ? O35 C34 C33 128.3(5) . . ? O35 C34 C37 114.5(4) . . ? C33 C34 C37 117.1(5) . . ? C34 O35 Mn1 128.1(3) . . ? F32 C36 F31 109.9(8) . . ? F32 C36 F33 108.6(7) . . ? F31 C36 F33 103.6(6) . . ? F32 C36 C32 114.9(5) . . ? F31 C36 C32 110.5(6) . . ? F33 C36 C32 108.9(6) . . ? F36 C37 F35 108.3(6) . . ? F36 C37 F34 105.5(5) . . ? F35 C37 F34 107.3(5) . . ? F36 C37 C34 112.6(5) . . ? F35 C37 C34 112.9(5) . . ? F34 C37 C34 109.8(5) . . ? O61 Mn2 O75 112.16(16) . . ? O61 Mn2 O71 87.57(14) . . ? O75 Mn2 O71 83.26(14) . . ? O61 Mn2 O65 83.30(13) . . ? O75 Mn2 O65 89.79(14) . . ? O71 Mn2 O65 165.52(16) . . ? O61 Mn2 N54 92.38(16) . . ? O75 Mn2 N54 155.29(15) . . ? O71 Mn2 N54 101.31(15) . . ? O65 Mn2 N54 90.31(15) . . ? O61 Mn2 N41 164.35(16) . . ? O75 Mn2 N41 83.19(16) . . ? O71 Mn2 N41 97.66(16) . . ? O65 Mn2 N41 94.09(15) . . ? N54 Mn2 N41 72.16(17) . . ? C45 N41 S42 113.8(4) . . ? C45 N41 Mn2 116.1(3) . . ? S42 N41 Mn2 130.1(3) . . ? N41 S42 S43 93.29(19) . . ? N44 S43 S42 95.3(2) . . ? C45 N44 S43 113.3(4) . . ? N44 C45 N41 124.3(5) . . ? N44 C45 C46 121.4(5) . . ? N41 C45 C46 114.2(5) . . ? N54 C46 O47 116.0(4) . . ? N54 C46 C45 123.5(5) . . ? O47 C46 C45 120.5(5) . . ? C46 O47 C48 103.3(4) . . ? C53 C48 C49 124.4(6) . . ? C53 C48 O47 108.8(5) . . ? C49 C48 O47 126.8(6) . . ? C50 C49 C48 114.4(7) . . ? C50 C49 H49A 122.8 . . ? C48 C49 H49A 122.8 . . ? C49 C50 C51 122.6(6) . . ? C49 C50 H50A 118.7 . . ? C51 C50 H50A 118.7 . . ? C52 C51 C50 120.9(6) . . ? C52 C51 H51A 119.5 . . ? C50 C51 H51A 119.5 . . ? C51 C52 C53 117.3(6) . . ? C51 C52 H52A 121.4 . . ? C53 C52 H52A 121.4 . . ? C48 C53 C52 120.4(5) . . ? C48 C53 N54 107.7(5) . . ? C52 C53 N54 131.9(5) . . ? C46 N54 C53 104.3(5) . . ? C46 N54 Mn2 113.8(3) . . ? C53 N54 Mn2 141.5(4) . . ? C62 O61 Mn2 129.0(3) . . ? O61 C62 C63 127.4(5) . . ? O61 C62 C66 115.2(4) . . ? C63 C62 C66 117.4(4) . . ? C64 C63 C62 122.3(5) . . ? C64 C63 H63A 118.9 . . ? C62 C63 H63A 118.9 . . ? O65 C64 C63 129.0(5) . . ? O65 C64 C67 113.0(4) . . ? C63 C64 C67 118.0(5) . . ? C64 O65 Mn2 126.9(3) . . ? F61 C66 F63 107.5(6) . . ? F61 C66 F62 105.7(6) . . ? F63 C66 F62 106.6(6) . . ? F61 C66 C62 113.5(5) . . ? F63 C66 C62 111.5(5) . . ? F62 C66 C62 111.6(5) . . ? F66 C67 F65 107.4(6) . . ? F66 C67 F64 105.8(5) . . ? F65 C67 F64 107.4(6) . . ? F66 C67 C64 112.5(5) . . ? F65 C67 C64 113.8(4) . . ? F64 C67 C64 109.5(5) . . ? C72 O71 Mn2 128.4(3) . . ? O71 C72 C73 128.3(5) . . ? O71 C72 C76 113.9(5) . . ? C73 C72 C76 117.8(5) . . ? C72 C73 C74 123.5(5) . . ? C72 C73 H73A 118.3 . . ? C74 C73 H73A 118.3 . . ? O75 C74 C73 127.1(5) . . ? O75 C74 C77 113.9(5) . . ? C73 C74 C77 119.0(5) . . ? C74 O75 Mn2 129.5(3) . . ? F72 C76 F73 106.0(6) . . ? F72 C76 F71 108.8(6) . . ? F73 C76 F71 104.6(6) . . ? F72 C76 C72 113.7(5) . . ? F73 C76 C72 114.4(5) . . ? F71 C76 C72 108.9(5) . . ? F75 C77 F74 107.9(7) . . ? F75 C77 F76 107.7(6) . . ? F74 C77 F76 105.1(6) . . ? F75 C77 C74 114.3(6) . . ? F74 C77 C74 111.4(5) . . ? F76 C77 C74 110.0(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 O25 Mn1 N1 C5 -8.1(9) . . . . ? O31 Mn1 N1 C5 -169.0(4) . . . . ? O35 Mn1 N1 C5 -86.0(4) . . . . ? O21 Mn1 N1 C5 102.1(4) . . . . ? N14 Mn1 N1 C5 8.3(3) . . . . ? O25 Mn1 N1 S2 159.3(5) . . . . ? O31 Mn1 N1 S2 -1.6(3) . . . . ? O35 Mn1 N1 S2 81.5(3) . . . . ? O21 Mn1 N1 S2 -90.5(3) . . . . ? N14 Mn1 N1 S2 175.7(4) . . . . ? C5 N1 S2 S3 0.9(4) . . . . ? Mn1 N1 S2 S3 -166.7(3) . . . . ? N1 S2 S3 N4 -0.9(2) . . . . ? S2 S3 N4 C5 0.8(4) . . . . ? S3 N4 C5 N1 -0.3(7) . . . . ? S3 N4 C5 C6 179.0(4) . . . . ? S2 N1 C5 N4 -0.5(7) . . . . ? Mn1 N1 C5 N4 168.9(4) . . . . ? S2 N1 C5 C6 -179.9(3) . . . . ? Mn1 N1 C5 C6 -10.4(5) . . . . ? N4 C5 C6 N14 -172.6(5) . . . . ? N1 C5 C6 N14 6.8(7) . . . . ? N4 C5 C6 O7 8.1(7) . . . . ? N1 C5 C6 O7 -172.5(4) . . . . ? N14 C6 O7 C8 0.2(6) . . . . ? C5 C6 O7 C8 179.5(4) . . . . ? C6 O7 C8 C9 179.9(6) . . . . ? C6 O7 C8 C13 0.0(5) . . . . ? C13 C8 C9 C10 0.8(9) . . . . ? O7 C8 C9 C10 -179.1(5) . . . . ? C8 C9 C10 C11 -0.8(10) . . . . ? C9 C10 C11 C12 0.1(11) . . . . ? C10 C11 C12 C13 0.8(9) . . . . ? C9 C8 C13 C12 0.0(9) . . . . ? O7 C8 C13 C12 180.0(4) . . . . ? C9 C8 C13 N14 179.9(5) . . . . ? O7 C8 C13 N14 -0.2(6) . . . . ? C11 C12 C13 C8 -0.8(8) . . . . ? C11 C12 C13 N14 179.4(5) . . . . ? O7 C6 N14 C13 -0.3(6) . . . . ? C5 C6 N14 C13 -179.6(4) . . . . ? O7 C6 N14 Mn1 -179.9(3) . . . . ? C5 C6 N14 Mn1 0.8(6) . . . . ? C8 C13 N14 C6 0.3(5) . . . . ? C12 C13 N14 C6 -179.9(5) . . . . ? C8 C13 N14 Mn1 179.7(4) . . . . ? C12 C13 N14 Mn1 -0.5(9) . . . . ? O25 Mn1 N14 C6 171.6(3) . . . . ? O31 Mn1 N14 C6 2.2(6) . . . . ? O35 Mn1 N14 C6 84.5(4) . . . . ? O21 Mn1 N14 C6 -104.6(3) . . . . ? N1 Mn1 N14 C6 -4.6(3) . . . . ? O25 Mn1 N14 C13 -7.7(5) . . . . ? O31 Mn1 N14 C13 -177.1(4) . . . . ? O35 Mn1 N14 C13 -94.8(5) . . . . ? O21 Mn1 N14 C13 76.0(5) . . . . ? N1 Mn1 N14 C13 176.1(5) . . . . ? O25 Mn1 O21 C22 7.3(5) . . . . ? O31 Mn1 O21 C22 116.0(5) . . . . ? O35 Mn1 O21 C22 54.3(8) . . . . ? N14 Mn1 O21 C22 -86.4(5) . . . . ? N1 Mn1 O21 C22 -159.7(5) . . . . ? Mn1 O21 C22 C23 -5.9(9) . . . . ? Mn1 O21 C22 C26 174.0(4) . . . . ? O21 C22 C23 C24 -2.3(10) . . . . ? C26 C22 C23 C24 177.8(5) . . . . ? C22 C23 C24 O25 6.7(9) . . . . ? C22 C23 C24 C27 -176.8(5) . . . . ? C23 C24 O25 Mn1 -1.9(8) . . . . ? C27 C24 O25 Mn1 -178.4(4) . . . . ? O31 Mn1 O25 C24 -91.5(5) . . . . ? O35 Mn1 O25 C24 -173.2(5) . . . . ? O21 Mn1 O25 C24 -3.7(5) . . . . ? N14 Mn1 O25 C24 92.9(5) . . . . ? N1 Mn1 O25 C24 108.6(7) . . . . ? O21 C22 C26 F22 -149.6(7) . . . . ? C23 C22 C26 F22 30.2(9) . . . . ? O21 C22 C26 F21 85.3(8) . . . . ? C23 C22 C26 F21 -94.8(7) . . . . ? O21 C22 C26 F23 -29.6(8) . . . . ? C23 C22 C26 F23 150.3(7) . . . . ? O25 C24 C27 F24 -154.2(5) . . . . ? C23 C24 C27 F24 28.9(7) . . . . ? O25 C24 C27 F25 -32.5(7) . . . . ? C23 C24 C27 F25 150.6(5) . . . . ? O25 C24 C27 F26 85.4(6) . . . . ? C23 C24 C27 F26 -91.5(6) . . . . ? O25 Mn1 O31 C32 -93.6(5) . . . . ? O35 Mn1 O31 C32 -9.4(5) . . . . ? O21 Mn1 O31 C32 -176.5(5) . . . . ? N14 Mn1 O31 C32 75.2(6) . . . . ? N1 Mn1 O31 C32 81.7(5) . . . . ? Mn1 O31 C32 C33 5.9(9) . . . . ? Mn1 O31 C32 C36 -175.9(5) . . . . ? O31 C32 C33 C34 3.9(10) . . . . ? C36 C32 C33 C34 -174.2(6) . . . . ? C32 C33 C34 O35 -5.8(10) . . . . ? C32 C33 C34 C37 170.1(6) . . . . ? C33 C34 O35 Mn1 -2.2(9) . . . . ? C37 C34 O35 Mn1 -178.2(4) . . . . ? O25 Mn1 O35 C34 116.7(5) . . . . ? O31 Mn1 O35 C34 7.6(5) . . . . ? O21 Mn1 O35 C34 70.1(7) . . . . ? N14 Mn1 O35 C34 -149.1(5) . . . . ? N1 Mn1 O35 C34 -76.8(5) . . . . ? O31 C32 C36 F32 -178.9(8) . . . . ? C33 C32 C36 F32 -0.6(11) . . . . ? O31 C32 C36 F31 -54.0(8) . . . . ? C33 C32 C36 F31 124.4(6) . . . . ? O31 C32 C36 F33 59.2(8) . . . . ? C33 C32 C36 F33 -122.5(6) . . . . ? O35 C34 C37 F36 -29.1(7) . . . . ? C33 C34 C37 F36 154.5(5) . . . . ? O35 C34 C37 F35 -152.1(6) . . . . ? C33 C34 C37 F35 31.5(9) . . . . ? O35 C34 C37 F34 88.2(6) . . . . ? C33 C34 C37 F34 -88.2(6) . . . . ? O61 Mn2 N41 C45 -7.4(8) . . . . ? O75 Mn2 N41 C45 -176.4(4) . . . . ? O71 Mn2 N41 C45 101.3(4) . . . . ? O65 Mn2 N41 C45 -87.1(4) . . . . ? N54 Mn2 N41 C45 1.9(3) . . . . ? O61 Mn2 N41 S42 172.7(4) . . . . ? O75 Mn2 N41 S42 3.7(3) . . . . ? O71 Mn2 N41 S42 -78.5(3) . . . . ? O65 Mn2 N41 S42 93.0(3) . . . . ? N54 Mn2 N41 S42 -178.0(3) . . . . ? C45 N41 S42 S43 -1.5(4) . . . . ? Mn2 N41 S42 S43 178.4(3) . . . . ? N41 S42 S43 N44 0.5(3) . . . . ? S42 S43 N44 C45 0.6(4) . . . . ? S43 N44 C45 N41 -2.0(7) . . . . ? S43 N44 C45 C46 -179.7(4) . . . . ? S42 N41 C45 N44 2.5(7) . . . . ? Mn2 N41 C45 N44 -177.5(4) . . . . ? S42 N41 C45 C46 -179.7(3) . . . . ? Mn2 N41 C45 C46 0.4(6) . . . . ? N44 C45 C46 N54 173.2(5) . . . . ? N41 C45 C46 N54 -4.7(7) . . . . ? N44 C45 C46 O47 -7.4(8) . . . . ? N41 C45 C46 O47 174.6(4) . . . . ? N54 C46 O47 C48 -0.4(5) . . . . ? C45 C46 O47 C48 -179.8(4) . . . . ? C46 O47 C48 C53 -0.1(5) . . . . ? C46 O47 C48 C49 -179.4(6) . . . . ? C53 C48 C49 C50 0.6(9) . . . . ? O47 C48 C49 C50 179.8(5) . . . . ? C48 C49 C50 C51 0.5(9) . . . . ? C49 C50 C51 C52 -1.3(11) . . . . ? C50 C51 C52 C53 0.9(9) . . . . ? C49 C48 C53 C52 -1.0(9) . . . . ? O47 C48 C53 C52 179.7(4) . . . . ? C49 C48 C53 N54 179.8(5) . . . . ? O47 C48 C53 N54 0.5(6) . . . . ? C51 C52 C53 C48 0.2(8) . . . . ? C51 C52 C53 N54 179.2(5) . . . . ? O47 C46 N54 C53 0.7(5) . . . . ? C45 C46 N54 C53 -179.9(4) . . . . ? O47 C46 N54 Mn2 -173.0(3) . . . . ? C45 C46 N54 Mn2 6.3(6) . . . . ? C48 C53 N54 C46 -0.7(5) . . . . ? C52 C53 N54 C46 -179.8(5) . . . . ? C48 C53 N54 Mn2 170.0(4) . . . . ? C52 C53 N54 Mn2 -9.0(9) . . . . ? O61 Mn2 N54 C46 173.4(4) . . . . ? O75 Mn2 N54 C46 -0.1(6) . . . . ? O71 Mn2 N54 C46 -98.6(4) . . . . ? O65 Mn2 N54 C46 90.1(4) . . . . ? N41 Mn2 N54 C46 -4.1(3) . . . . ? O61 Mn2 N54 C53 3.2(5) . . . . ? O75 Mn2 N54 C53 -170.3(4) . . . . ? O71 Mn2 N54 C53 91.2(5) . . . . ? O65 Mn2 N54 C53 -80.1(5) . . . . ? N41 Mn2 N54 C53 -174.3(5) . . . . ? O75 Mn2 O61 C62 98.5(5) . . . . ? O71 Mn2 O61 C62 -179.8(5) . . . . ? O65 Mn2 O61 C62 11.5(5) . . . . ? N54 Mn2 O61 C62 -78.5(5) . . . . ? N41 Mn2 O61 C62 -69.7(8) . . . . ? Mn2 O61 C62 C63 -3.5(8) . . . . ? Mn2 O61 C62 C66 175.7(4) . . . . ? O61 C62 C63 C64 -8.5(9) . . . . ? C66 C62 C63 C64 172.3(5) . . . . ? C62 C63 C64 O65 5.5(9) . . . . ? C62 C63 C64 C67 -171.0(5) . . . . ? C63 C64 O65 Mn2 8.7(8) . . . . ? C67 C64 O65 Mn2 -174.7(4) . . . . ? O61 Mn2 O65 C64 -13.7(4) . . . . ? O75 Mn2 O65 C64 -126.1(4) . . . . ? O71 Mn2 O65 C64 -65.0(7) . . . . ? N54 Mn2 O65 C64 78.6(4) . . . . ? N41 Mn2 O65 C64 150.7(4) . . . . ? O61 C62 C66 F61 151.7(6) . . . . ? C63 C62 C66 F61 -29.0(8) . . . . ? O61 C62 C66 F63 -86.7(7) . . . . ? C63 C62 C66 F63 92.6(7) . . . . ? O61 C62 C66 F62 32.4(8) . . . . ? C63 C62 C66 F62 -148.3(6) . . . . ? O65 C64 C67 F66 45.6(7) . . . . ? C63 C64 C67 F66 -137.4(6) . . . . ? O65 C64 C67 F65 168.0(6) . . . . ? C63 C64 C67 F65 -15.0(8) . . . . ? O65 C64 C67 F64 -71.8(7) . . . . ? C63 C64 C67 F64 105.2(6) . . . . ? O61 Mn2 O71 C72 -112.8(5) . . . . ? O75 Mn2 O71 C72 -0.1(5) . . . . ? O65 Mn2 O71 C72 -61.9(8) . . . . ? N54 Mn2 O71 C72 155.3(5) . . . . ? N41 Mn2 O71 C72 82.1(5) . . . . ? Mn2 O71 C72 C73 -0.4(9) . . . . ? Mn2 O71 C72 C76 -179.7(4) . . . . ? O71 C72 C73 C74 1.7(10) . . . . ? C76 C72 C73 C74 -179.1(6) . . . . ? C72 C73 C74 O75 -2.5(10) . . . . ? C72 C73 C74 C77 179.4(6) . . . . ? C73 C74 O75 Mn2 2.0(9) . . . . ? C77 C74 O75 Mn2 -179.9(4) . . . . ? O61 Mn2 O75 C74 83.9(5) . . . . ? O71 Mn2 O75 C74 -0.6(5) . . . . ? O65 Mn2 O75 C74 166.6(5) . . . . ? N54 Mn2 O75 C74 -103.1(5) . . . . ? N41 Mn2 O75 C74 -99.2(5) . . . . ? O71 C72 C76 F72 140.1(6) . . . . ? C73 C72 C76 F72 -39.2(9) . . . . ? O71 C72 C76 F73 18.2(8) . . . . ? C73 C72 C76 F73 -161.2(6) . . . . ? O71 C72 C76 F71 -98.3(7) . . . . ? C73 C72 C76 F71 82.3(7) . . . . ? O75 C74 C77 F75 172.2(7) . . . . ? C73 C74 C77 F75 -9.5(10) . . . . ? O75 C74 C77 F74 49.6(8) . . . . ? C73 C74 C77 F74 -132.1(6) . . . . ? O75 C74 C77 F76 -66.6(7) . . . . ? C73 C74 C77 F76 111.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.533 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.079 # Attachment '- ef2900mCu_final.cif' data_ef2900m _database_code_depnum_ccdc_archive 'CCDC 774620' #TrackingRef '- ef2900mCu_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H4 N3 O S2' _chemical_formula_sum 'C8 H4 N3 O S2' _chemical_formula_weight 222.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.83340(10) _cell_length_b 12.0493(2) _cell_length_c 33.7548(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.8910(10) _cell_angle_gamma 90.00 _cell_volume 3592.30(8) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7467 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 68.13 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 5.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2282 _exptl_absorpt_correction_T_max 0.2467 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker D8, SMART 6000' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16670 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 6.21 _diffrn_reflns_theta_max 66.58 _reflns_number_total 6022 _reflns_number_gt 4829 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker D8' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 2001)' _computing_publication_material SHELXTL/PC _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^)+(0.0516P)^2^+1.5483P] 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 SHELXL _refine_ls_extinction_coef 0.00264(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6022 _refine_ls_number_parameters 506 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 S11 S 0.56922(8) 1.11840(6) 0.10273(2) 0.0590(2) Uani 1 1 d . . . S12 S 0.69590(10) 1.16016(7) 0.15285(2) 0.0680(2) Uani 1 1 d . . . N13 N 0.6143(3) 1.0692(2) 0.18164(6) 0.0605(6) Uani 1 1 d . . . C14 C 0.5092(3) 1.0105(2) 0.16319(7) 0.0489(6) Uani 1 1 d . . . N15 N 0.4723(2) 1.02239(18) 0.12498(6) 0.0523(5) Uani 1 1 d . . . C16 C 0.4283(3) 0.9263(2) 0.18619(7) 0.0500(6) Uani 1 1 d . . . O17 O 0.4963(2) 0.88553(16) 0.21912(5) 0.0590(5) Uani 1 1 d . . . C18 C 0.3930(3) 0.8083(2) 0.23286(7) 0.0465(6) Uani 1 1 d . . . C19 C 0.4030(4) 0.7388(3) 0.26522(8) 0.0642(8) Uani 1 1 d . . . H19A H 0.4882 0.7394 0.2828 0.077 Uiso 1 1 calc R . . C20 C 0.2825(4) 0.6687(3) 0.27058(8) 0.0684(8) Uani 1 1 d . . . H20A H 0.2850 0.6183 0.2923 0.082 Uiso 1 1 calc R . . C21 C 0.1569(4) 0.6692(3) 0.24517(8) 0.0634(8) Uani 1 1 d . . . H21A H 0.0754 0.6200 0.2502 0.076 Uiso 1 1 calc R . . C22 C 0.1474(3) 0.7389(2) 0.21294(8) 0.0532(6) Uani 1 1 d . . . H22A H 0.0616 0.7392 0.1956 0.064 Uiso 1 1 calc R . . C23 C 0.2696(3) 0.8084(2) 0.20712(7) 0.0434(5) Uani 1 1 d . . . N24 N 0.2965(2) 0.88577(16) 0.17743(5) 0.0411(4) Uani 1 1 d . . . S31 S 0.93577(8) 0.97516(7) 0.12789(2) 0.0636(2) Uani 1 1 d . . . S32 S 0.79481(8) 0.94503(6) 0.079088(19) 0.0569(2) Uani 1 1 d . . . N33 N 0.7040(3) 0.84385(19) 0.10030(6) 0.0539(5) Uani 1 1 d . . . C34 C 0.7526(3) 0.8220(2) 0.13724(7) 0.0491(6) Uani 1 1 d . . . N35 N 0.8629(3) 0.8782(2) 0.15539(7) 0.0580(6) Uani 1 1 d . . . C36 C 0.6817(3) 0.7302(2) 0.15829(7) 0.0478(6) Uani 1 1 d . . . O37 O 0.7570(2) 0.68939(16) 0.19077(5) 0.0553(5) Uani 1 1 d . . . C38 C 0.6674(3) 0.6018(2) 0.20224(7) 0.0488(6) Uani 1 1 d . . . C39 C 0.6916(4) 0.5275(3) 0.23287(8) 0.0675(8) Uani 1 1 d . . . H39A H 0.7779 0.5317 0.2499 0.081 Uiso 1 1 calc R . . C40 C 0.5828(4) 0.4472(3) 0.23699(9) 0.0754(9) Uani 1 1 d . . . H40A H 0.5948 0.3934 0.2574 0.090 Uiso 1 1 calc R . . C41 C 0.4554(4) 0.4422(3) 0.21226(9) 0.0736(9) Uani 1 1 d . . . H41A H 0.3823 0.3858 0.2165 0.088 Uiso 1 1 calc R . . C42 C 0.4327(4) 0.5170(3) 0.18182(8) 0.0628(8) Uani 1 1 d . . . H42A H 0.3457 0.5137 0.1650 0.075 Uiso 1 1 calc R . . C43 C 0.5430(3) 0.5969(2) 0.17706(7) 0.0478(6) Uani 1 1 d . . . N44 N 0.5570(2) 0.68164(18) 0.14882(6) 0.0493(5) Uani 1 1 d . . . S51 S 0.25716(9) 0.85672(7) 0.078518(19) 0.0649(2) Uani 1 1 d . . . S52 S 0.35152(9) 0.97226(6) 0.04004(2) 0.0630(2) Uani 1 1 d . . . N53 N 0.2436(3) 0.9392(2) 0.00233(6) 0.0603(6) Uani 1 1 d . . . C54 C 0.1455(3) 0.8587(2) 0.01056(7) 0.0500(6) Uani 1 1 d . . . N55 N 0.1375(3) 0.8093(2) 0.04552(6) 0.0622(6) Uani 1 1 d . . . C56 C 0.0417(3) 0.8206(2) -0.02120(7) 0.0492(6) Uani 1 1 d . . . O57 O -0.0311(2) 0.72348(16) -0.01367(5) 0.0585(5) Uani 1 1 d . . . C58 C -0.1180(3) 0.7055(2) -0.04731(7) 0.0514(6) Uani 1 1 d . . . C59 C -0.2144(3) 0.6184(3) -0.05510(9) 0.0657(8) Uani 1 1 d . . . H59A H -0.2290 0.5597 -0.0368 0.079 Uiso 1 1 calc R . . C60 C -0.2876(3) 0.6221(3) -0.09101(9) 0.0658(8) Uani 1 1 d . . . H60A H -0.3560 0.5641 -0.0980 0.079 Uiso 1 1 calc R . . C61 C -0.2651(4) 0.7077(3) -0.11753(10) 0.0708(9) Uani 1 1 d . . . H61A H -0.3185 0.7067 -0.1422 0.085 Uiso 1 1 calc R . . C62 C -0.1677(4) 0.7944(3) -0.10936(9) 0.0706(9) Uani 1 1 d . . . H62A H -0.1530 0.8531 -0.1277 0.085 Uiso 1 1 calc R . . C63 C -0.0918(3) 0.7918(2) -0.07288(8) 0.0524(6) Uani 1 1 d . . . N64 N 0.0123(3) 0.86528(19) -0.05524(6) 0.0565(6) Uani 1 1 d . . . S71 S 0.48946(10) 0.67983(7) 0.05600(2) 0.0664(2) Uani 1 1 d . . . S72 S 0.58441(8) 0.79162(7) 0.01620(2) 0.0645(2) Uani 1 1 d . . . N73 N 0.4825(3) 0.7504(2) -0.02163(6) 0.0596(6) Uani 1 1 d . . . C74 C 0.3924(3) 0.6664(2) -0.01339(7) 0.0518(6) Uani 1 1 d . . . N75 N 0.3816(3) 0.6216(2) 0.02255(7) 0.0661(7) Uani 1 1 d . . . C76 C 0.2991(3) 0.6186(2) -0.04577(7) 0.0504(6) Uani 1 1 d . . . O77 O 0.2252(2) 0.52252(15) -0.03692(5) 0.0613(5) Uani 1 1 d . . . C78 C 0.1496(3) 0.4966(2) -0.07201(7) 0.0526(6) Uani 1 1 d . . . C79 C 0.0568(4) 0.4072(3) -0.07924(9) 0.0692(8) Uani 1 1 d . . . H79A H 0.0374 0.3524 -0.0597 0.083 Uiso 1 1 calc R . . C80 C -0.0061(4) 0.4029(3) -0.11658(9) 0.0672(8) Uani 1 1 d . . . H80A H -0.0724 0.3435 -0.1232 0.081 Uiso 1 1 calc R . . C81 C 0.0244(4) 0.4827(3) -0.14485(9) 0.0663(8) Uani 1 1 d . . . H81A H -0.0212 0.4764 -0.1704 0.080 Uiso 1 1 calc R . . C82 C 0.1192(4) 0.5711(3) -0.13688(8) 0.0671(8) Uani 1 1 d . . . H82A H 0.1402 0.6254 -0.1564 0.081 Uiso 1 1 calc R . . C83 C 0.1829(3) 0.5773(2) -0.09896(7) 0.0506(6) Uani 1 1 d . . . N84 N 0.2791(3) 0.65565(19) -0.08113(6) 0.0556(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 S11 0.0655(4) 0.0574(4) 0.0536(4) 0.0147(3) -0.0107(3) -0.0121(3) S12 0.0838(5) 0.0647(5) 0.0555(4) -0.0033(3) -0.0030(4) -0.0325(4) N13 0.0707(15) 0.0673(15) 0.0434(12) -0.0034(11) -0.0029(11) -0.0235(12) C14 0.0502(15) 0.0490(15) 0.0473(14) -0.0019(11) -0.0011(11) -0.0047(11) N15 0.0501(13) 0.0551(13) 0.0514(12) 0.0081(10) -0.0103(10) -0.0087(10) C16 0.0616(16) 0.0465(15) 0.0421(13) 0.0003(11) 0.0077(12) 0.0013(12) O17 0.0557(11) 0.0670(12) 0.0540(11) 0.0035(9) -0.0043(9) -0.0095(9) C18 0.0521(15) 0.0505(15) 0.0367(12) -0.0009(11) -0.0007(11) -0.0036(11) C19 0.073(2) 0.074(2) 0.0455(15) 0.0050(14) -0.0131(14) -0.0028(15) C20 0.095(2) 0.0623(19) 0.0484(16) 0.0131(14) 0.0023(16) -0.0090(16) C21 0.075(2) 0.0594(18) 0.0564(16) -0.0026(14) 0.0099(15) -0.0171(14) C22 0.0537(15) 0.0561(16) 0.0498(14) -0.0048(13) -0.0015(12) -0.0100(12) C23 0.0473(14) 0.0485(14) 0.0342(11) -0.0049(10) 0.0008(10) -0.0013(10) N24 0.0439(11) 0.0456(11) 0.0337(10) -0.0001(8) -0.0008(8) -0.0046(8) S31 0.0530(4) 0.0769(5) 0.0609(4) 0.0100(4) -0.0063(3) -0.0142(3) S32 0.0683(4) 0.0617(4) 0.0407(3) 0.0043(3) 0.0001(3) -0.0088(3) N33 0.0662(14) 0.0542(13) 0.0409(11) 0.0030(10) -0.0085(10) -0.0062(10) C34 0.0535(15) 0.0508(15) 0.0428(13) 0.0018(11) -0.0043(11) 0.0003(11) N35 0.0555(14) 0.0659(15) 0.0524(13) 0.0094(11) -0.0131(11) -0.0063(11) C36 0.0567(16) 0.0498(15) 0.0366(12) 0.0028(11) -0.0048(11) 0.0035(12) O37 0.0551(11) 0.0645(12) 0.0458(10) 0.0074(9) -0.0128(8) -0.0020(9) C38 0.0545(16) 0.0522(16) 0.0395(13) 0.0030(11) -0.0057(11) 0.0004(11) C39 0.072(2) 0.078(2) 0.0522(16) 0.0178(15) -0.0163(14) -0.0009(16) C40 0.097(2) 0.075(2) 0.0540(17) 0.0237(16) -0.0051(17) -0.0060(18) C41 0.096(2) 0.067(2) 0.0572(17) 0.0103(15) 0.0006(17) -0.0222(17) C42 0.0721(19) 0.070(2) 0.0456(15) -0.0003(14) -0.0122(13) -0.0172(15) C43 0.0585(16) 0.0509(15) 0.0339(12) -0.0004(11) -0.0054(11) -0.0008(11) N44 0.0591(14) 0.0528(13) 0.0355(10) 0.0035(9) -0.0099(9) -0.0035(10) S51 0.0645(5) 0.0950(6) 0.0352(3) -0.0075(3) -0.0025(3) -0.0220(4) S52 0.0743(5) 0.0591(4) 0.0550(4) -0.0024(3) -0.0201(3) -0.0192(3) N53 0.0695(15) 0.0612(15) 0.0495(13) 0.0027(11) -0.0174(11) -0.0171(12) C54 0.0472(15) 0.0612(17) 0.0413(13) -0.0031(12) -0.0054(11) -0.0048(12) N55 0.0550(14) 0.0893(18) 0.0422(12) -0.0059(12) -0.0015(10) -0.0231(12) C56 0.0450(14) 0.0573(16) 0.0452(14) -0.0074(12) -0.0027(11) -0.0068(11) O57 0.0609(11) 0.0685(13) 0.0457(10) -0.0014(9) -0.0082(8) -0.0193(9) C58 0.0490(15) 0.0607(17) 0.0444(14) -0.0131(12) -0.0031(11) -0.0059(12) C59 0.071(2) 0.070(2) 0.0557(16) -0.0086(15) -0.0007(14) -0.0215(15) C60 0.0619(18) 0.070(2) 0.0651(18) -0.0237(16) -0.0053(14) -0.0145(14) C61 0.073(2) 0.074(2) 0.0645(19) -0.0178(17) -0.0251(16) -0.0028(16) C62 0.081(2) 0.067(2) 0.0629(18) 0.0014(15) -0.0291(16) -0.0129(16) C63 0.0478(15) 0.0546(16) 0.0545(15) -0.0086(13) -0.0106(12) 0.0013(11) N64 0.0577(14) 0.0589(14) 0.0523(13) -0.0025(11) -0.0180(11) -0.0072(10) S71 0.0896(6) 0.0624(5) 0.0464(4) -0.0016(3) -0.0231(4) -0.0047(4) S72 0.0563(4) 0.0863(6) 0.0508(4) -0.0123(4) -0.0063(3) -0.0178(4) N73 0.0611(14) 0.0770(16) 0.0407(11) -0.0094(11) -0.0008(10) -0.0187(12) C74 0.0601(16) 0.0544(16) 0.0407(13) -0.0054(12) -0.0065(12) -0.0066(12) N75 0.0967(19) 0.0558(15) 0.0454(12) -0.0008(11) -0.0176(12) -0.0161(13) C76 0.0577(16) 0.0520(15) 0.0415(13) -0.0085(11) -0.0016(12) -0.0074(12) O77 0.0882(14) 0.0537(11) 0.0417(10) -0.0049(8) -0.0075(9) -0.0190(10) C78 0.0647(17) 0.0533(16) 0.0398(13) -0.0107(12) -0.0027(12) -0.0054(12) C79 0.096(2) 0.0577(18) 0.0540(16) -0.0105(14) -0.0024(16) -0.0240(16) C80 0.078(2) 0.0633(19) 0.0602(17) -0.0201(15) -0.0036(15) -0.0192(15) C81 0.076(2) 0.073(2) 0.0499(16) -0.0160(15) -0.0114(14) -0.0100(15) C82 0.084(2) 0.0684(19) 0.0487(15) -0.0022(14) -0.0095(15) -0.0208(16) C83 0.0556(16) 0.0546(16) 0.0416(13) -0.0113(12) -0.0005(11) -0.0056(12) N84 0.0660(15) 0.0609(14) 0.0400(11) -0.0048(10) -0.0024(10) -0.0180(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S11 N15 1.630(2) . ? S11 S12 2.0757(10) . ? S12 N13 1.639(2) . ? N13 C14 1.316(3) . ? C14 N15 1.333(3) . ? C14 C16 1.469(3) . ? C16 N24 1.293(3) . ? C16 O17 1.348(3) . ? O17 C18 1.388(3) . ? C18 C19 1.378(4) . ? C18 C23 1.383(3) . ? C19 C20 1.373(4) . ? C19 H19A 0.9500 . ? C20 C21 1.392(4) . ? C20 H20A 0.9500 . ? C21 C22 1.376(4) . ? C21 H21A 0.9500 . ? C22 C23 1.383(3) . ? C22 H22A 0.9500 . ? C23 N24 1.391(3) . ? S31 N35 1.631(2) . ? S31 S32 2.0813(10) . ? S32 N33 1.631(2) . ? N33 C34 1.339(3) . ? C34 N35 1.328(3) . ? C34 C36 1.461(4) . ? C36 N44 1.284(3) . ? C36 O37 1.365(3) . ? O37 C38 1.378(3) . ? C38 C43 1.380(3) . ? C38 C39 1.382(4) . ? C39 C40 1.372(4) . ? C39 H39A 0.9500 . ? C40 C41 1.392(5) . ? C40 H40A 0.9500 . ? C41 C42 1.380(4) . ? C41 H41A 0.9500 . ? C42 C43 1.381(4) . ? C42 H42A 0.9500 . ? C43 N44 1.403(3) . ? S51 N55 1.627(2) . ? S51 S52 2.0865(11) . ? S52 N53 1.628(2) . ? N53 C54 1.333(3) . ? C54 N55 1.324(3) . ? C54 C56 1.473(3) . ? C56 N64 1.292(3) . ? C56 O57 1.361(3) . ? O57 C58 1.378(3) . ? C58 C63 1.373(4) . ? C58 C59 1.374(4) . ? C59 C60 1.366(4) . ? C59 H59A 0.9500 . ? C60 C61 1.382(4) . ? C60 H60A 0.9500 . ? C61 C62 1.379(4) . ? C61 H61A 0.9500 . ? C62 C63 1.393(4) . ? C62 H62A 0.9500 . ? C63 N64 1.403(3) . ? S71 N75 1.625(2) . ? S71 S72 2.0875(11) . ? S72 N73 1.629(2) . ? N73 C74 1.319(3) . ? C74 N75 1.333(3) . ? C74 C76 1.476(3) . ? C76 N84 1.284(3) . ? C76 O77 1.364(3) . ? O77 C78 1.386(3) . ? C78 C83 1.367(4) . ? C78 C79 1.373(4) . ? C79 C80 1.370(4) . ? C79 H79A 0.9500 . ? C80 C81 1.384(4) . ? C80 H80A 0.9500 . ? C81 C82 1.378(4) . ? C81 H81A 0.9500 . ? C82 C83 1.392(4) . ? C82 H82A 0.9500 . ? C83 N84 1.400(3) . ? 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 N15 S11 S12 94.41(8) . . ? N13 S12 S11 94.85(8) . . ? C14 N13 S12 113.10(19) . . ? N13 C14 N15 124.1(2) . . ? N13 C14 C16 117.8(2) . . ? N15 C14 C16 118.2(2) . . ? C14 N15 S11 113.58(18) . . ? N24 C16 O17 116.0(2) . . ? N24 C16 C14 125.7(2) . . ? O17 C16 C14 118.3(2) . . ? C16 O17 C18 103.5(2) . . ? C19 C18 C23 122.6(2) . . ? C19 C18 O17 129.6(2) . . ? C23 C18 O17 107.8(2) . . ? C20 C19 C18 116.0(3) . . ? C20 C19 H19A 122.0 . . ? C18 C19 H19A 122.0 . . ? C19 C20 C21 121.9(3) . . ? C19 C20 H20A 119.1 . . ? C21 C20 H20A 119.1 . . ? C22 C21 C20 121.9(3) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 116.4(3) . . ? C21 C22 H22A 121.8 . . ? C23 C22 H22A 121.8 . . ? C22 C23 C18 121.3(2) . . ? C22 C23 N24 130.5(2) . . ? C18 C23 N24 108.2(2) . . ? C16 N24 C23 104.6(2) . . ? N35 S31 S32 95.11(8) . . ? N33 S32 S31 94.31(8) . . ? C34 N33 S32 113.77(19) . . ? N35 C34 N33 123.5(2) . . ? N35 C34 C36 118.6(2) . . ? N33 C34 C36 117.9(2) . . ? C34 N35 S31 113.32(18) . . ? N44 C36 O37 116.2(2) . . ? N44 C36 C34 126.6(2) . . ? O37 C36 C34 117.2(2) . . ? C36 O37 C38 103.13(19) . . ? O37 C38 C43 108.3(2) . . ? O37 C38 C39 128.6(2) . . ? C43 C38 C39 123.1(3) . . ? C40 C39 C38 115.6(3) . . ? C40 C39 H39A 122.2 . . ? C38 C39 H39A 122.2 . . ? C39 C40 C41 122.1(3) . . ? C39 C40 H40A 119.0 . . ? C41 C40 H40A 119.0 . . ? C42 C41 C40 121.7(3) . . ? C42 C41 H41A 119.2 . . ? C40 C41 H41A 119.2 . . ? C41 C42 C43 116.6(3) . . ? C41 C42 H42A 121.7 . . ? C43 C42 H42A 121.7 . . ? C38 C43 C42 120.9(2) . . ? C38 C43 N44 108.1(2) . . ? C42 C43 N44 131.0(2) . . ? C36 N44 C43 104.3(2) . . ? N55 S51 S52 93.99(9) . . ? N53 S52 S51 95.09(9) . . ? C54 N53 S52 112.94(18) . . ? N55 C54 N53 123.8(2) . . ? N55 C54 C56 117.8(2) . . ? N53 C54 C56 118.3(2) . . ? C54 N55 S51 114.15(19) . . ? N64 C56 O57 115.8(2) . . ? N64 C56 C54 129.2(2) . . ? O57 C56 C54 115.0(2) . . ? C56 O57 C58 103.9(2) . . ? C63 C58 C59 124.6(3) . . ? C63 C58 O57 107.6(2) . . ? C59 C58 O57 127.8(3) . . ? C60 C59 C58 115.4(3) . . ? C60 C59 H59A 122.3 . . ? C58 C59 H59A 122.3 . . ? C59 C60 C61 121.9(3) . . ? C59 C60 H60A 119.1 . . ? C61 C60 H60A 119.1 . . ? C62 C61 C60 122.1(3) . . ? C62 C61 H61A 118.9 . . ? C60 C61 H61A 118.9 . . ? C61 C62 C63 116.7(3) . . ? C61 C62 H62A 121.6 . . ? C63 C62 H62A 121.6 . . ? C58 C63 C62 119.3(3) . . ? C58 C63 N64 109.1(2) . . ? C62 C63 N64 131.6(3) . . ? C56 N64 C63 103.6(2) . . ? N75 S71 S72 93.93(9) . . ? N73 S72 S71 94.88(9) . . ? C74 N73 S72 113.35(19) . . ? N73 C74 N75 123.7(2) . . ? N73 C74 C76 118.4(2) . . ? N75 C74 C76 118.0(2) . . ? C74 N75 S71 114.1(2) . . ? N84 C76 O77 116.0(2) . . ? N84 C76 C74 128.3(2) . . ? O77 C76 C74 115.7(2) . . ? C76 O77 C78 103.30(19) . . ? C83 C78 C79 125.0(3) . . ? C83 C78 O77 107.6(2) . . ? C79 C78 O77 127.4(3) . . ? C80 C79 C78 115.2(3) . . ? C80 C79 H79A 122.4 . . ? C78 C79 H79A 122.4 . . ? C79 C80 C81 121.8(3) . . ? C79 C80 H80A 119.1 . . ? C81 C80 H80A 119.1 . . ? C82 C81 C80 121.7(3) . . ? C82 C81 H81A 119.1 . . ? C80 C81 H81A 119.1 . . ? C81 C82 C83 117.2(3) . . ? C81 C82 H82A 121.4 . . ? C83 C82 H82A 121.4 . . ? C78 C83 C82 119.0(2) . . ? C78 C83 N84 109.2(2) . . ? C82 C83 N84 131.7(3) . . ? C76 N84 C83 103.8(2) . . ? 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 N15 S11 S12 N13 -0.15(13) . . . . ? S11 S12 N13 C14 -0.1(2) . . . . ? S12 N13 C14 N15 0.4(4) . . . . ? S12 N13 C14 C16 -179.93(19) . . . . ? N13 C14 N15 S11 -0.5(4) . . . . ? C16 C14 N15 S11 179.79(19) . . . . ? S12 S11 N15 C14 0.3(2) . . . . ? N13 C14 C16 N24 157.9(3) . . . . ? N15 C14 C16 N24 -22.4(4) . . . . ? N13 C14 C16 O17 -23.1(4) . . . . ? N15 C14 C16 O17 156.6(2) . . . . ? N24 C16 O17 C18 0.2(3) . . . . ? C14 C16 O17 C18 -178.8(2) . . . . ? C16 O17 C18 C19 178.4(3) . . . . ? C16 O17 C18 C23 -0.1(3) . . . . ? C23 C18 C19 C20 0.1(4) . . . . ? O17 C18 C19 C20 -178.3(3) . . . . ? C18 C19 C20 C21 -1.0(5) . . . . ? C19 C20 C21 C22 0.9(5) . . . . ? C20 C21 C22 C23 0.1(4) . . . . ? C21 C22 C23 C18 -1.0(4) . . . . ? C21 C22 C23 N24 178.5(2) . . . . ? C19 C18 C23 C22 0.9(4) . . . . ? O17 C18 C23 C22 179.6(2) . . . . ? C19 C18 C23 N24 -178.7(2) . . . . ? O17 C18 C23 N24 0.0(3) . . . . ? O17 C16 N24 C23 -0.3(3) . . . . ? C14 C16 N24 C23 178.7(2) . . . . ? C22 C23 N24 C16 -179.4(3) . . . . ? C18 C23 N24 C16 0.2(3) . . . . ? N35 S31 S32 N33 -0.14(13) . . . . ? S31 S32 N33 C34 -0.4(2) . . . . ? S32 N33 C34 N35 1.0(4) . . . . ? S32 N33 C34 C36 -177.98(19) . . . . ? N33 C34 N35 S31 -1.1(4) . . . . ? C36 C34 N35 S31 177.85(19) . . . . ? S32 S31 N35 C34 0.6(2) . . . . ? N35 C34 C36 N44 165.5(3) . . . . ? N33 C34 C36 N44 -15.5(4) . . . . ? N35 C34 C36 O37 -16.3(4) . . . . ? N33 C34 C36 O37 162.7(2) . . . . ? N44 C36 O37 C38 1.6(3) . . . . ? C34 C36 O37 C38 -176.7(2) . . . . ? C36 O37 C38 C43 -1.7(3) . . . . ? C36 O37 C38 C39 177.5(3) . . . . ? O37 C38 C39 C40 -179.2(3) . . . . ? C43 C38 C39 C40 -0.1(5) . . . . ? C38 C39 C40 C41 -0.9(5) . . . . ? C39 C40 C41 C42 0.9(6) . . . . ? C40 C41 C42 C43 0.2(5) . . . . ? O37 C38 C43 C42 -179.5(2) . . . . ? C39 C38 C43 C42 1.2(4) . . . . ? O37 C38 C43 N44 1.3(3) . . . . ? C39 C38 C43 N44 -177.9(3) . . . . ? C41 C42 C43 C38 -1.2(4) . . . . ? C41 C42 C43 N44 177.8(3) . . . . ? O37 C36 N44 C43 -0.8(3) . . . . ? C34 C36 N44 C43 177.3(2) . . . . ? C38 C43 N44 C36 -0.3(3) . . . . ? C42 C43 N44 C36 -179.4(3) . . . . ? N55 S51 S52 N53 0.02(14) . . . . ? S51 S52 N53 C54 0.4(2) . . . . ? S52 N53 C54 N55 -0.9(4) . . . . ? S52 N53 C54 C56 -179.7(2) . . . . ? N53 C54 N55 S51 0.9(4) . . . . ? C56 C54 N55 S51 179.7(2) . . . . ? S52 S51 N55 C54 -0.4(2) . . . . ? N55 C54 C56 N64 168.6(3) . . . . ? N53 C54 C56 N64 -12.5(4) . . . . ? N55 C54 C56 O57 -12.7(4) . . . . ? N53 C54 C56 O57 166.2(2) . . . . ? N64 C56 O57 C58 -0.4(3) . . . . ? C54 C56 O57 C58 -179.3(2) . . . . ? C56 O57 C58 C63 0.3(3) . . . . ? C56 O57 C58 C59 -179.8(3) . . . . ? C63 C58 C59 C60 -0.6(4) . . . . ? O57 C58 C59 C60 179.6(3) . . . . ? C58 C59 C60 C61 0.2(5) . . . . ? C59 C60 C61 C62 0.0(5) . . . . ? C60 C61 C62 C63 0.2(5) . . . . ? C59 C58 C63 C62 0.8(4) . . . . ? O57 C58 C63 C62 -179.4(3) . . . . ? C59 C58 C63 N64 179.9(3) . . . . ? O57 C58 C63 N64 -0.2(3) . . . . ? C61 C62 C63 C58 -0.5(5) . . . . ? C61 C62 C63 N64 -179.5(3) . . . . ? O57 C56 N64 C63 0.3(3) . . . . ? C54 C56 N64 C63 179.0(3) . . . . ? C58 C63 N64 C56 -0.1(3) . . . . ? C62 C63 N64 C56 179.0(3) . . . . ? N75 S71 S72 N73 2.36(14) . . . . ? S71 S72 N73 C74 -2.6(2) . . . . ? S72 N73 C74 N75 2.1(4) . . . . ? S72 N73 C74 C76 -177.4(2) . . . . ? N73 C74 N75 S71 0.2(4) . . . . ? C76 C74 N75 S71 179.7(2) . . . . ? S72 S71 N75 C74 -1.7(2) . . . . ? N73 C74 C76 N84 -8.9(5) . . . . ? N75 C74 C76 N84 171.6(3) . . . . ? N73 C74 C76 O77 170.9(2) . . . . ? N75 C74 C76 O77 -8.6(4) . . . . ? N84 C76 O77 C78 0.4(3) . . . . ? C74 C76 O77 C78 -179.4(2) . . . . ? C76 O77 C78 C83 0.0(3) . . . . ? C76 O77 C78 C79 -179.5(3) . . . . ? C83 C78 C79 C80 -0.7(5) . . . . ? O77 C78 C79 C80 178.8(3) . . . . ? C78 C79 C80 C81 0.8(5) . . . . ? C79 C80 C81 C82 -0.3(5) . . . . ? C80 C81 C82 C83 -0.3(5) . . . . ? C79 C78 C83 C82 0.2(5) . . . . ? O77 C78 C83 C82 -179.4(3) . . . . ? C79 C78 C83 N84 179.2(3) . . . . ? O77 C78 C83 N84 -0.4(3) . . . . ? C81 C82 C83 C78 0.4(4) . . . . ? C81 C82 C83 N84 -178.3(3) . . . . ? O77 C76 N84 C83 -0.7(3) . . . . ? C74 C76 N84 C83 179.1(3) . . . . ? C78 C83 N84 C76 0.6(3) . . . . ? C82 C83 N84 C76 179.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.416 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.059