# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Cheng Ma' _publ_contact_author_email MCORG@ZJU.EDU.CN _publ_section_title ; Thiazepine Moiety-Controlled Regioselective Rearrangements of 7-Oxanorbornadiene Derivatives ; loop_ _publ_author_name 'Cheng Ma.' 'Hanfeng Ding.' 'Weijun Yao.' 'Yiping Zhang.' # Attachment '3a.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 653549' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Br N O S' _chemical_formula_weight 338.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Br Br -0.2901 2.4595 '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' _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 6.952(4) _cell_length_b 7.636(6) _cell_length_c 15.489(11) _cell_angle_alpha 78.16(3) _cell_angle_beta 87.74(3) _cell_angle_gamma 66.38(3) _cell_volume 736.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2152 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 23.0 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 2.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.526 _exptl_absorpt_correction_T_max 0.692 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 7311 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3345 _reflns_number_gt 2271 _reflns_threshold_expression >2sigma(I) _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^)+(0.0349P)^2^+0.3173P] 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 3345 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0798 _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 Br Br -0.27238(6) 0.21059(5) 0.47791(3) 0.07538(16) Uani 1 1 d . . . S1 S 0.54898(11) 0.64500(10) 0.08264(5) 0.04910(19) Uani 1 1 d . . . N1 N 0.5320(3) 0.8596(3) 0.19021(14) 0.0435(5) Uani 1 1 d . . . O1 O 0.3038(3) 0.4610(3) 0.14516(14) 0.0620(5) Uani 1 1 d . . . C1 C -0.1026(4) 0.2984(4) 0.3970(2) 0.0507(7) Uani 1 1 d . . . C2 C 0.0515(5) 0.3418(4) 0.4291(2) 0.0561(7) Uani 1 1 d . . . H008 H 0.0777 0.3198 0.4896 0.067 Uiso 1 1 calc R . . C3 C 0.1666(5) 0.4184(4) 0.37045(19) 0.0518(7) Uani 1 1 d . . . H010 H 0.2677 0.4515 0.3920 0.062 Uiso 1 1 calc R . . C4 C 0.1344(4) 0.4466(4) 0.28044(18) 0.0437(6) Uani 1 1 d . . . C5 C -0.0163(4) 0.3939(4) 0.24950(19) 0.0481(7) Uani 1 1 d . . . H1 H -0.0356 0.4067 0.1891 0.058 Uiso 1 1 calc R . . C6 C -0.1368(4) 0.3233(4) 0.3072(2) 0.0531(7) Uani 1 1 d . . . H017 H -0.2401 0.2925 0.2859 0.064 Uiso 1 1 calc R . . C7 C 0.2604(4) 0.5235(4) 0.21481(19) 0.0472(6) Uani 1 1 d . . . C8 C 0.3287(4) 0.6618(4) 0.23488(19) 0.0470(6) Uani 1 1 d . . . H99 H 0.2877 0.7095 0.2863 0.056 Uiso 1 1 calc R . . C9 C 0.4566(4) 0.7271(4) 0.17853(18) 0.0438(6) Uani 1 1 d . . . C10 C 0.4736(5) 0.9604(4) 0.2643(2) 0.0532(7) Uani 1 1 d . . . H00A H 0.3313 0.9775 0.2794 0.064 Uiso 1 1 calc R . . H00B H 0.4754 1.0891 0.2461 0.064 Uiso 1 1 calc R . . C11 C 0.6177(6) 0.8518(5) 0.3444(2) 0.0667(9) Uani 1 1 d . . . H01D H 0.6122 0.7264 0.3642 0.100 Uiso 1 1 calc R . . H01E H 0.5746 0.9249 0.3904 0.100 Uiso 1 1 calc R . . H01F H 0.7589 0.8346 0.3299 0.100 Uiso 1 1 calc R . . C12 C 0.6688(4) 0.8913(4) 0.12603(19) 0.0468(6) Uani 1 1 d . . . C13 C 0.6960(4) 0.7872(4) 0.06413(19) 0.0476(6) Uani 1 1 d . . . C14 C 0.7677(5) 1.0309(5) 0.1319(2) 0.0611(8) Uani 1 1 d . . . H01A H 0.8558 1.0358 0.0830 0.092 Uiso 1 1 calc R . . H01B H 0.8510 0.9875 0.1862 0.092 Uiso 1 1 calc R . . H01C H 0.6597 1.1587 0.1304 0.092 Uiso 1 1 calc R . . C15 C 0.8316(5) 0.7794(5) -0.0134(2) 0.0615(8) Uani 1 1 d . . . H01G H 0.8189 0.6910 -0.0465 0.092 Uiso 1 1 calc R . . H01H H 0.9754 0.7349 0.0069 0.092 Uiso 1 1 calc R . . H01I H 0.7878 0.9075 -0.0503 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0681(2) 0.0758(3) 0.0853(3) -0.00591(19) 0.01285(18) -0.03797(19) S1 0.0570(4) 0.0460(4) 0.0473(4) -0.0099(3) -0.0007(3) -0.0233(3) N1 0.0495(12) 0.0341(11) 0.0479(13) -0.0082(10) -0.0008(10) -0.0177(10) O1 0.0741(14) 0.0679(14) 0.0609(13) -0.0268(11) 0.0140(11) -0.0405(12) C1 0.0470(15) 0.0384(15) 0.0640(19) -0.0063(13) 0.0005(14) -0.0163(12) C2 0.0624(18) 0.0513(18) 0.0541(18) -0.0050(14) -0.0054(14) -0.0245(15) C3 0.0549(16) 0.0523(17) 0.0538(17) -0.0088(14) -0.0065(14) -0.0276(14) C4 0.0414(14) 0.0337(14) 0.0534(16) -0.0103(12) -0.0019(12) -0.0114(11) C5 0.0454(15) 0.0468(16) 0.0527(16) -0.0140(13) -0.0048(13) -0.0166(13) C6 0.0447(15) 0.0464(16) 0.073(2) -0.0169(14) -0.0038(14) -0.0203(13) C7 0.0440(15) 0.0398(15) 0.0553(18) -0.0079(13) -0.0026(13) -0.0148(12) C8 0.0510(15) 0.0395(15) 0.0510(16) -0.0119(12) 0.0008(13) -0.0172(12) C9 0.0471(14) 0.0323(13) 0.0492(16) -0.0060(12) -0.0043(12) -0.0136(11) C10 0.0611(17) 0.0378(15) 0.0643(19) -0.0179(14) 0.0112(15) -0.0208(13) C11 0.082(2) 0.072(2) 0.0516(18) -0.0238(16) 0.0027(17) -0.0319(19) C12 0.0500(15) 0.0375(14) 0.0501(16) -0.0030(12) -0.0018(13) -0.0174(12) C13 0.0496(16) 0.0409(15) 0.0493(16) -0.0034(13) -0.0013(13) -0.0177(12) C14 0.072(2) 0.0563(19) 0.066(2) -0.0123(16) 0.0052(16) -0.0373(16) C15 0.070(2) 0.060(2) 0.0573(19) -0.0093(15) 0.0077(16) -0.0306(16) _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 Br C1 1.893(3) . ? S1 C9 1.731(3) . ? S1 C13 1.745(3) . ? N1 C9 1.356(3) . ? N1 C12 1.401(4) . ? N1 C10 1.466(4) . ? O1 C7 1.246(3) . ? C1 C2 1.378(4) . ? C1 C6 1.382(4) . ? C2 C3 1.381(4) . ? C2 H008 0.9300 . ? C3 C4 1.379(4) . ? C3 H010 0.9300 . ? C4 C5 1.395(4) . ? C4 C7 1.498(4) . ? C5 C6 1.377(4) . ? C5 H1 0.9300 . ? C6 H017 0.9300 . ? C7 C8 1.409(4) . ? C8 C9 1.384(4) . ? C8 H99 0.9300 . ? C10 C11 1.497(4) . ? C10 H00A 0.9700 . ? C10 H00B 0.9700 . ? C11 H01D 0.9600 . ? C11 H01E 0.9600 . ? C11 H01F 0.9600 . ? C12 C13 1.329(4) . ? C12 C14 1.500(4) . ? C13 C15 1.493(4) . ? C14 H01A 0.9600 . ? C14 H01B 0.9600 . ? C14 H01C 0.9600 . ? C15 H01G 0.9600 . ? C15 H01H 0.9600 . ? C15 H01I 0.9600 . ? 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 C9 S1 C13 91.20(13) . . ? C9 N1 C12 114.6(2) . . ? C9 N1 C10 122.2(2) . . ? C12 N1 C10 123.3(2) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 Br 118.9(2) . . ? C6 C1 Br 120.4(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H008 120.3 . . ? C3 C2 H008 120.3 . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H010 119.4 . . ? C2 C3 H010 119.4 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 C7 122.8(2) . . ? C5 C4 C7 118.7(3) . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H1 119.6 . . ? C4 C5 H1 119.6 . . ? C5 C6 C1 119.3(3) . . ? C5 C6 H017 120.3 . . ? C1 C6 H017 120.3 . . ? O1 C7 C8 122.4(3) . . ? O1 C7 C4 119.0(2) . . ? C8 C7 C4 118.6(3) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H99 119.8 . . ? C7 C8 H99 119.8 . . ? N1 C9 C8 126.0(3) . . ? N1 C9 S1 109.8(2) . . ? C8 C9 S1 124.2(2) . . ? N1 C10 C11 112.8(2) . . ? N1 C10 H00A 109.0 . . ? C11 C10 H00A 109.0 . . ? N1 C10 H00B 109.0 . . ? C11 C10 H00B 109.0 . . ? H00A C10 H00B 107.8 . . ? C10 C11 H01D 109.5 . . ? C10 C11 H01E 109.5 . . ? H01D C11 H01E 109.5 . . ? C10 C11 H01F 109.5 . . ? H01D C11 H01F 109.5 . . ? H01E C11 H01F 109.5 . . ? C13 C12 N1 113.0(2) . . ? C13 C12 C14 126.8(3) . . ? N1 C12 C14 120.2(3) . . ? C12 C13 C15 128.5(3) . . ? C12 C13 S1 111.4(2) . . ? C15 C13 S1 120.1(2) . . ? C12 C14 H01A 109.5 . . ? C12 C14 H01B 109.5 . . ? H01A C14 H01B 109.5 . . ? C12 C14 H01C 109.5 . . ? H01A C14 H01C 109.5 . . ? H01B C14 H01C 109.5 . . ? C13 C15 H01G 109.5 . . ? C13 C15 H01H 109.5 . . ? H01G C15 H01H 109.5 . . ? C13 C15 H01I 109.5 . . ? H01G C15 H01I 109.5 . . ? H01H C15 H01I 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.332 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.060 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 653550' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 O4' _chemical_formula_sum 'C24 H20 O4' _chemical_formula_weight 372.40 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.979(4) _cell_length_b 8.876(4) _cell_length_c 18.629(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.484(14) _cell_angle_gamma 90.00 _cell_volume 1959.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2756 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 24.7 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID IP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 18781 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4476 _reflns_number_gt 3135 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0468P)^2^+0.1999P] 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 4476 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.78602(8) -0.11423(11) 1.08092(5) 0.0565(3) Uani 1 1 d . . . O2 O 0.77457(9) -0.37410(11) 1.06578(5) 0.0612(3) Uani 1 1 d . . . O4 O 0.62471(10) -0.38377(12) 1.16022(6) 0.0730(3) Uani 1 1 d . . . O3 O 0.67609(11) -0.15134(13) 1.19490(6) 0.0788(3) Uani 1 1 d . . . C14 C 0.75509(10) -0.02425(14) 1.01990(6) 0.0437(3) Uani 1 1 d . . . C16 C 0.57863(11) -0.04032(15) 0.91869(7) 0.0480(3) Uani 1 1 d . . . H16 H 0.5940 0.0464 0.8939 0.058 Uiso 1 1 calc R . . C21 C 0.71596(11) -0.24351(14) 1.07907(7) 0.0480(3) Uani 1 1 d . . . C8 C 0.91050(10) 0.15525(15) 1.06247(7) 0.0456(3) Uani 1 1 d . . . C4 C 0.78958(10) 0.18255(14) 0.93962(7) 0.0449(3) Uani 1 1 d . . . C5 C 0.74414(12) 0.32636(15) 0.93770(8) 0.0535(3) Uani 1 1 d . . . H5 H 0.7300 0.3716 0.9805 0.064 Uiso 1 1 calc R . . C15 C 0.65168(10) -0.08825(14) 0.97964(6) 0.0418(3) Uani 1 1 d . . . C23 C 0.67186(12) -0.25084(16) 1.15223(7) 0.0522(3) Uani 1 1 d . . . C20 C 0.62496(11) -0.21684(14) 1.01595(7) 0.0450(3) Uani 1 1 d . . . C7 C 0.81602(10) 0.09818(14) 1.00931(6) 0.0434(3) Uani 1 1 d . . . C19 C 0.52886(12) -0.29910(15) 0.99385(8) 0.0562(4) Uani 1 1 d . . . H19 H 0.5119 -0.3839 1.0195 0.067 Uiso 1 1 calc R . . C13 C 0.91080(12) 0.14633(17) 1.13716(7) 0.0568(4) Uani 1 1 d . . . H13 H 0.8518 0.0980 1.1551 0.068 Uiso 1 1 calc R . . C9 C 1.00132(11) 0.22708(17) 1.03850(8) 0.0568(4) Uani 1 1 d . . . H9 H 1.0035 0.2342 0.9889 0.068 Uiso 1 1 calc R . . C17 C 0.48292(11) -0.12446(17) 0.89591(7) 0.0547(3) Uani 1 1 d . . . H17 H 0.4341 -0.0942 0.8550 0.066 Uiso 1 1 calc R . . C18 C 0.45817(13) -0.25262(17) 0.93261(8) 0.0598(4) Uani 1 1 d . . . H18 H 0.3935 -0.3078 0.9160 0.072 Uiso 1 1 calc R . . C12 C 0.99767(13) 0.20846(19) 1.18486(8) 0.0665(4) Uani 1 1 d . . . H12 H 0.9963 0.2022 1.2346 0.080 Uiso 1 1 calc R . . C6 C 0.71975(13) 0.40306(19) 0.87264(9) 0.0692(4) Uani 1 1 d . . . H6 H 0.6882 0.4989 0.8719 0.083 Uiso 1 1 calc R . . C3 C 0.81285(13) 0.11991(18) 0.87522(8) 0.0605(4) Uani 1 1 d . . . H3 H 0.8448 0.0244 0.8754 0.073 Uiso 1 1 calc R . . C11 C 1.08635(13) 0.27960(19) 1.15955(10) 0.0688(4) Uani 1 1 d . . . H11 H 1.1446 0.3217 1.1919 0.083 Uiso 1 1 calc R . . C10 C 1.08792(12) 0.28780(19) 1.08626(9) 0.0674(4) Uani 1 1 d . . . H10 H 1.1479 0.3347 1.0688 0.081 Uiso 1 1 calc R . . C1 C 0.74163(15) 0.3390(2) 0.80924(9) 0.0768(5) Uani 1 1 d . . . H1 H 0.7245 0.3907 0.7656 0.092 Uiso 1 1 calc R . . C2 C 0.78885(16) 0.1987(2) 0.81067(8) 0.0752(5) Uani 1 1 d . . . H2 H 0.8050 0.1557 0.7678 0.090 Uiso 1 1 calc R . . C22 C 0.86976(15) -0.4087(2) 1.11933(9) 0.0790(5) Uani 1 1 d . . . H22A H 0.9197 -0.3235 1.1256 0.118 Uiso 1 1 calc R . . H22B H 0.9091 -0.4940 1.1037 0.118 Uiso 1 1 calc R . . H22C H 0.8443 -0.4316 1.1646 0.118 Uiso 1 1 calc R . . C24 C 0.57677(17) -0.4037(3) 1.22674(10) 0.0958(6) Uani 1 1 d . . . H24A H 0.6350 -0.3922 1.2677 0.144 Uiso 1 1 calc R . . H24B H 0.5445 -0.5025 1.2274 0.144 Uiso 1 1 calc R . . H24C H 0.5192 -0.3294 1.2291 0.144 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0677(6) 0.0499(6) 0.0480(5) 0.0134(4) -0.0049(4) -0.0124(4) O2 0.0798(7) 0.0510(6) 0.0534(6) 0.0015(4) 0.0116(5) 0.0131(5) O4 0.1023(8) 0.0634(7) 0.0583(6) 0.0104(5) 0.0278(6) -0.0153(6) O3 0.1217(10) 0.0655(7) 0.0502(6) -0.0104(5) 0.0160(6) 0.0029(7) C14 0.0513(7) 0.0434(7) 0.0365(6) 0.0043(5) 0.0066(5) -0.0002(6) C16 0.0559(7) 0.0497(8) 0.0388(7) 0.0021(6) 0.0090(6) -0.0025(6) C21 0.0652(8) 0.0358(7) 0.0430(7) 0.0032(5) 0.0079(6) -0.0034(6) C8 0.0477(7) 0.0450(7) 0.0449(7) -0.0019(5) 0.0091(6) -0.0006(6) C4 0.0479(7) 0.0446(7) 0.0430(7) 0.0030(5) 0.0097(5) -0.0107(5) C5 0.0579(8) 0.0477(8) 0.0550(8) 0.0015(6) 0.0083(6) -0.0079(6) C15 0.0506(7) 0.0400(7) 0.0362(6) -0.0019(5) 0.0109(5) -0.0020(5) C23 0.0682(9) 0.0469(8) 0.0406(7) 0.0046(6) 0.0048(6) 0.0034(6) C20 0.0605(7) 0.0377(6) 0.0378(6) -0.0024(5) 0.0110(5) -0.0038(6) C7 0.0471(6) 0.0438(7) 0.0403(6) 0.0006(5) 0.0100(5) -0.0031(5) C19 0.0742(9) 0.0434(7) 0.0519(8) -0.0044(6) 0.0130(7) -0.0156(7) C13 0.0583(8) 0.0648(9) 0.0479(8) -0.0023(7) 0.0097(6) -0.0057(7) C9 0.0536(8) 0.0636(9) 0.0549(8) -0.0035(7) 0.0136(6) -0.0093(7) C17 0.0554(8) 0.0655(9) 0.0418(7) -0.0050(6) 0.0028(6) -0.0032(7) C18 0.0625(8) 0.0626(9) 0.0538(8) -0.0119(7) 0.0068(7) -0.0178(7) C12 0.0713(10) 0.0770(11) 0.0484(8) -0.0058(7) -0.0002(7) 0.0000(8) C6 0.0727(10) 0.0546(9) 0.0760(11) 0.0186(8) -0.0034(8) -0.0105(8) C3 0.0773(10) 0.0581(9) 0.0500(8) -0.0001(7) 0.0224(7) -0.0074(7) C11 0.0549(9) 0.0693(10) 0.0768(11) -0.0125(8) -0.0080(8) -0.0044(8) C10 0.0517(8) 0.0740(11) 0.0762(11) -0.0076(8) 0.0087(7) -0.0140(7) C1 0.0888(12) 0.0831(13) 0.0546(10) 0.0263(9) -0.0020(8) -0.0263(10) C2 0.0969(12) 0.0876(13) 0.0442(8) 0.0050(8) 0.0213(8) -0.0215(10) C22 0.0863(11) 0.0795(12) 0.0701(11) 0.0168(9) 0.0079(9) 0.0254(10) C24 0.1023(14) 0.1214(17) 0.0703(11) 0.0359(11) 0.0348(10) -0.0057(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.3939(15) . ? O1 C21 1.4190(16) . ? O2 C21 1.3961(16) . ? O2 C22 1.4331(19) . ? O4 C23 1.3259(17) . ? O4 C24 1.4514(19) . ? O3 C23 1.1843(17) . ? C14 C7 1.3398(17) . ? C14 C15 1.4648(17) . ? C16 C17 1.3816(19) . ? C16 C15 1.3939(17) . ? C16 H16 0.9300 . ? C21 C20 1.4996(18) . ? C21 C23 1.534(2) . ? C8 C9 1.3903(19) . ? C8 C13 1.3933(19) . ? C8 C7 1.4790(17) . ? C4 C5 1.3860(19) . ? C4 C3 1.3874(19) . ? C4 C7 1.4918(17) . ? C5 C6 1.383(2) . ? C5 H5 0.9300 . ? C15 C20 1.3880(18) . ? C20 C19 1.3740(19) . ? C19 C18 1.380(2) . ? C19 H19 0.9300 . ? C13 C12 1.380(2) . ? C13 H13 0.9300 . ? C9 C10 1.373(2) . ? C9 H9 0.9300 . ? C17 C18 1.382(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C12 C11 1.377(2) . ? C12 H12 0.9300 . ? C6 C1 1.370(2) . ? C6 H6 0.9300 . ? C3 C2 1.384(2) . ? C3 H3 0.9300 . ? C11 C10 1.370(2) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? C1 C2 1.367(3) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C14 O1 C21 111.00(10) . . ? C21 O2 C22 115.07(12) . . ? C23 O4 C24 115.65(14) . . ? C7 C14 O1 119.98(11) . . ? C7 C14 C15 132.62(11) . . ? O1 C14 C15 107.36(10) . . ? C17 C16 C15 118.56(13) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? O2 C21 O1 111.38(11) . . ? O2 C21 C20 108.57(10) . . ? O1 C21 C20 104.50(10) . . ? O2 C21 C23 111.74(10) . . ? O1 C21 C23 107.02(10) . . ? C20 C21 C23 113.43(11) . . ? C9 C8 C13 117.39(12) . . ? C9 C8 C7 119.99(12) . . ? C13 C8 C7 122.56(12) . . ? C5 C4 C3 118.36(13) . . ? C5 C4 C7 121.13(12) . . ? C3 C4 C7 120.49(13) . . ? C6 C5 C4 120.48(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C20 C15 C16 119.06(11) . . ? C20 C15 C14 107.92(11) . . ? C16 C15 C14 132.89(12) . . ? O3 C23 O4 124.40(14) . . ? O3 C23 C21 125.34(13) . . ? O4 C23 C21 110.23(11) . . ? C19 C20 C15 122.29(12) . . ? C19 C20 C21 129.13(12) . . ? C15 C20 C21 108.58(11) . . ? C14 C7 C8 123.98(11) . . ? C14 C7 C4 119.01(11) . . ? C8 C7 C4 117.01(11) . . ? C20 C19 C18 118.28(13) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? C12 C13 C8 120.73(14) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C10 C9 C8 121.61(14) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C16 C17 C18 121.46(13) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 120.33(13) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C11 C12 C13 120.62(15) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C1 C6 C5 120.57(17) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C2 C3 C4 120.41(16) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C10 C11 C12 119.35(14) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C10 C9 120.31(14) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C2 C1 C6 119.50(15) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C1 C2 C3 120.65(16) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.155 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.028 # Attachment '8a_new.cif' data_8a _database_code_depnum_ccdc_archive 'CCDC 653551' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C28 H30 N O5 S), 2(C2 F3 O2), 5(H2 O)' _chemical_formula_sum 'C60 H70 F6 N2 O19 S2' _chemical_formula_weight 1301.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 14.258(3) _cell_length_b 15.677(3) _cell_length_c 17.381(4) _cell_angle_alpha 97.49(3) _cell_angle_beta 106.18(3) _cell_angle_gamma 115.38(3) _cell_volume 3228.4(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15502 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1364 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26071 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0916 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.20 _reflns_number_total 11577 _reflns_number_gt 5925 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.2P)^2] 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 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11577 _refine_ls_number_parameters 765 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1841 _refine_ls_R_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.3553 _refine_ls_wR_factor_gt 0.3182 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 S1 S 0.48200(13) 0.91066(11) 0.17707(9) 0.0559(5) Uani 1 1 d . . . S2 S 0.21161(13) 0.44309(11) 0.38803(10) 0.0598(5) Uani 1 1 d . . . N1 N 0.2672(4) 0.5001(3) 0.5421(3) 0.0521(12) Uani 1 1 d . . . N2 N 0.2918(4) 0.8206(3) 0.0664(3) 0.0530(12) Uani 1 1 d . . . O1 O 0.1576(4) 0.6219(4) 0.5011(3) 0.0782(14) Uani 1 1 d . . . O2 O 0.2096(4) 0.7141(4) 0.4179(3) 0.0817(14) Uani 1 1 d . . . O3 O 0.2249(4) 0.8676(3) 0.2053(3) 0.0791(14) Uani 1 1 d . . . O4 O 0.5541(4) 0.5584(3) 0.4081(3) 0.0812(15) Uani 1 1 d . . . O5 O 0.3114(4) 1.0233(3) 0.2813(3) 0.0708(12) Uani 1 1 d . . . O6 O 0.2708(3) 1.1281(3) 0.1605(3) 0.0585(11) Uani 1 1 d . . . O7 O 0.5801(4) 1.1210(3) 0.0375(3) 0.0644(11) Uani 1 1 d . . . O8 O 0.4357(3) 1.2319(3) 0.2629(2) 0.0589(11) Uani 1 1 d . . . O9 O 0.4369(4) 0.8242(3) 0.3825(2) 0.0558(10) Uani 1 1 d . . . O10 O 0.4504(4) 0.8446(3) 0.5158(2) 0.0615(11) Uani 1 1 d . . . O11 O -0.0470(8) 0.5539(7) 0.1792(5) 0.158(3) Uani 1 1 d . . . O12 O -0.1322(10) 0.5434(9) 0.2714(7) 0.200(5) Uani 1 1 d . . . O13 O 0.9140(6) 1.1056(5) 0.1822(5) 0.136(3) Uani 1 1 d . . . O14 O 0.9377(6) 1.0060(6) 0.0949(4) 0.118(2) Uani 1 1 d . . . C1 C 0.8893(8) 1.0459(6) 0.4778(8) 0.120(3) Uani 1 1 d . . . H1A H 0.9256 1.0914 0.5329 0.180 Uiso 1 1 calc R . . H1B H 0.8607 1.0745 0.4383 0.180 Uiso 1 1 calc R . . H1C H 0.9422 1.0315 0.4632 0.180 Uiso 1 1 calc R . . C2 C 0.2205(8) 0.5534(7) 0.1997(5) 0.099(3) Uani 1 1 d . . . H2A H 0.1591 0.5455 0.1563 0.119 Uiso 1 1 calc R . . C3 C 0.1743(7) 0.8350(6) 0.2650(6) 0.100(3) Uani 1 1 d . . . H3A H 0.1308 0.7644 0.2473 0.149 Uiso 1 1 calc R . . H3B H 0.1267 0.8628 0.2681 0.149 Uiso 1 1 calc R . . H3C H 0.2319 0.8563 0.3190 0.149 Uiso 1 1 calc R . . C4 C 0.5127(7) 0.7493(6) 0.1375(6) 0.091(2) Uani 1 1 d . . . H4A H 0.4751 0.6829 0.1020 0.137 Uiso 1 1 calc R . . H4B H 0.5343 0.7492 0.1950 0.137 Uiso 1 1 calc R . . H4C H 0.5782 0.7884 0.1266 0.137 Uiso 1 1 calc R . . C5 C 0.5097(10) 1.5239(6) 0.1054(7) 0.124(4) Uani 1 1 d . . . H5A H 0.4404 1.5201 0.0736 0.185 Uiso 1 1 calc R . . H5B H 0.5652 1.5573 0.0830 0.185 Uiso 1 1 calc R . . H5C H 0.5343 1.5597 0.1627 0.185 Uiso 1 1 calc R . . C6 C 0.0609(7) 0.6365(7) 0.4921(8) 0.121(4) Uani 1 1 d . . . H6A H 0.0209 0.6016 0.5241 0.181 Uiso 1 1 calc R . . H6B H 0.0124 0.6119 0.4342 0.181 Uiso 1 1 calc R . . H6C H 0.0858 0.7055 0.5121 0.181 Uiso 1 1 calc R . . C7 C 0.2662(7) 0.6550(5) 0.0017(5) 0.091(2) Uani 1 1 d . . . H7A H 0.3085 0.6208 0.0086 0.137 Uiso 1 1 calc R . . H7B H 0.2480 0.6613 -0.0540 0.137 Uiso 1 1 calc R . . H7C H 0.1984 0.6187 0.0110 0.137 Uiso 1 1 calc R . . C8 C 0.2759(8) 0.5020(7) 0.1845(5) 0.105(3) Uani 1 1 d . . . H8A H 0.2512 0.4611 0.1311 0.126 Uiso 1 1 calc R . . C9 C 0.7322(7) 0.8765(6) 0.4050(5) 0.083(2) Uani 1 1 d . . . H9A H 0.7500 0.8828 0.3577 0.099 Uiso 1 1 calc R . . C10 C 0.1092(7) 0.2475(5) 0.3915(5) 0.088(2) Uani 1 1 d . . . H10A H 0.0944 0.2087 0.4295 0.132 Uiso 1 1 calc R . . H10B H 0.1530 0.2322 0.3650 0.132 Uiso 1 1 calc R . . H10C H 0.0397 0.2328 0.3498 0.132 Uiso 1 1 calc R . . C11 C 0.2217(6) 1.1868(6) 0.1878(5) 0.089(2) Uani 1 1 d . . . H11A H 0.1445 1.1574 0.1518 0.133 Uiso 1 1 calc R . . H11B H 0.2617 1.2528 0.1849 0.133 Uiso 1 1 calc R . . H11C H 0.2271 1.1883 0.2443 0.133 Uiso 1 1 calc R . . C12 C 0.7461(6) 1.1478(5) 0.3004(5) 0.078(2) Uani 1 1 d . . . H12A H 0.8168 1.1556 0.3267 0.093 Uiso 1 1 calc R . . C13 C 0.6406(6) 0.7879(5) 0.4008(4) 0.0646(17) Uani 1 1 d . . . H13A H 0.5980 0.7377 0.3506 0.078 Uiso 1 1 calc R . . C14 C 0.3899(9) 1.3399(7) 0.0543(6) 0.096(3) Uani 1 1 d . . . H14A H 0.3311 1.3502 0.0273 0.115 Uiso 1 1 calc R . . C15 C 0.1947(6) 0.3459(6) 0.5862(5) 0.080(2) Uani 1 1 d . . . H15A H 0.1528 0.2758 0.5610 0.120 Uiso 1 1 calc R . . H15B H 0.1552 0.3659 0.6144 0.120 Uiso 1 1 calc R . . H15C H 0.2668 0.3633 0.6258 0.120 Uiso 1 1 calc R . . C16 C 0.2552(6) 0.6165(5) 0.2785(4) 0.0720(18) Uani 1 1 d . . . H16A H 0.2183 0.6509 0.2882 0.086 Uiso 1 1 calc R . . C17 C 0.3640(7) 0.5103(5) 0.2453(5) 0.080(2) Uani 1 1 d . . . H17A H 0.4000 0.4752 0.2351 0.096 Uiso 1 1 calc R . . C18 C 0.7684(6) 0.9396(5) 0.5459(5) 0.081(2) Uani 1 1 d . . . H18A H 0.8119 0.9901 0.5959 0.098 Uiso 1 1 calc R . . C19 C 0.7947(6) 0.9525(5) 0.4765(6) 0.078(2) Uani 1 1 d . . . C20 C 0.3116(6) 0.5605(5) 0.6291(4) 0.0649(16) Uani 1 1 d . . . H20A H 0.3490 0.6290 0.6319 0.097 Uiso 1 1 calc R . . H20B H 0.3636 0.5448 0.6638 0.097 Uiso 1 1 calc R . . H20C H 0.2511 0.5471 0.6482 0.097 Uiso 1 1 calc R . . C21 C 0.4838(7) 0.9290(5) 0.3973(4) 0.081(2) Uani 1 1 d . . . H21A H 0.4875 0.9454 0.3466 0.122 Uiso 1 1 calc R . . H21B H 0.5577 0.9616 0.4397 0.122 Uiso 1 1 calc R . . H21C H 0.4374 0.9499 0.4157 0.122 Uiso 1 1 calc R . . C22 C 0.4927(9) 1.4206(6) 0.1003(5) 0.081(2) Uani 1 1 d . . . C23 C 0.7088(5) 1.1426(5) 0.2172(4) 0.0632(16) Uani 1 1 d . . . H23A H 0.7541 1.1481 0.1866 0.076 Uiso 1 1 calc R . . C24 C 0.1789(5) 0.7915(5) 0.0089(5) 0.075(2) Uani 1 1 d . . . H24A H 0.1629 0.8445 0.0195 0.112 Uiso 1 1 calc R . . H24B H 0.1253 0.7341 0.0173 0.112 Uiso 1 1 calc R . . H24C H 0.1746 0.7767 -0.0478 0.112 Uiso 1 1 calc R . . C25 C 0.6787(5) 0.8534(5) 0.5440(4) 0.0671(17) Uani 1 1 d . . . H25A H 0.6619 0.8477 0.5917 0.080 Uiso 1 1 calc R . . C26 C 0.6771(5) 1.1412(5) 0.3455(4) 0.0641(17) Uani 1 1 d . . . H26A H 0.7040 1.1469 0.4022 0.077 Uiso 1 1 calc R . . C27 C 0.5783(7) 1.4038(5) 0.1403(5) 0.077(2) Uani 1 1 d . . . H27A H 0.6493 1.4567 0.1714 0.093 Uiso 1 1 calc R . . C28 C 0.3693(6) 1.2421(5) 0.0460(4) 0.0673(17) Uani 1 1 d . . . H28A H 0.2989 1.1894 0.0130 0.081 Uiso 1 1 calc R . . C29 C 0.1727(5) 0.3556(5) 0.4392(5) 0.0627(16) Uani 1 1 d . . . C30 C 0.3438(5) 1.0490(4) 0.0021(3) 0.0582(15) Uani 1 1 d . . . H30A H 0.3619 1.0712 -0.0434 0.087 Uiso 1 1 calc R . . H30B H 0.2737 1.0450 -0.0007 0.087 Uiso 1 1 calc R . . H30C H 0.3378 0.9851 -0.0017 0.087 Uiso 1 1 calc R . . C31 C 0.5590(6) 1.3084(5) 0.1342(4) 0.0650(17) Uani 1 1 d . . . H31A H 0.6179 1.2989 0.1624 0.078 Uiso 1 1 calc R . . C32 C 0.2235(5) 0.6639(4) 0.4617(4) 0.0600(16) Uani 1 1 d . . . C33 C 0.4352(6) 0.7921(4) 0.1204(4) 0.0569(15) Uani 1 1 d . . . C34 C 0.2090(5) 0.3963(4) 0.5206(4) 0.0586(16) Uani 1 1 d . . . C35 C 0.3464(5) 0.6260(4) 0.3417(3) 0.0504(14) Uani 1 1 d . . . C36 C 0.3342(6) 0.7557(4) 0.0636(4) 0.0600(16) Uani 1 1 d . . . C37 C 0.4003(5) 0.5734(4) 0.3246(4) 0.0572(15) Uani 1 1 d . . . C39 C 0.4942(5) 0.5967(4) 0.3978(4) 0.0575(16) Uani 1 1 d . . . C40 C 0.5135(4) 0.6799(4) 0.4672(3) 0.0468(13) Uani 1 1 d . . . C41 C 0.6140(5) 0.7754(4) 0.4698(4) 0.0526(14) Uani 1 1 d . . . C42 C 0.5394(5) 0.6574(5) 0.5494(4) 0.0623(16) Uani 1 1 d . . . H42A H 0.6088 0.6563 0.5640 0.093 Uiso 1 1 calc R . . H42B H 0.4804 0.5943 0.5449 0.093 Uiso 1 1 calc R . . H42C H 0.5453 0.7072 0.5919 0.093 Uiso 1 1 calc R . . C43 C 0.4287(5) 0.7919(4) 0.4473(3) 0.0474(13) Uani 1 1 d . . . C44 C 0.2887(5) 0.9628(4) 0.2191(4) 0.0517(14) Uani 1 1 d . . . C45 C 0.3284(5) 0.9832(4) 0.1489(3) 0.0448(12) Uani 1 1 d . . . H45A H 0.2627 0.9696 0.1012 0.054 Uiso 1 1 calc R . . C46 C 0.3207(4) 0.6422(4) 0.4826(3) 0.0460(13) Uani 1 1 d . . . H46A H 0.3671 0.6783 0.5417 0.055 Uiso 1 1 calc R . . C47 C 0.4346(5) 1.1209(4) 0.0841(3) 0.0459(13) Uani 1 1 d . . . C48 C 0.2763(4) 0.5352(4) 0.4775(4) 0.0474(13) Uani 1 1 d . . . C49 C 0.3615(4) 0.9074(4) 0.1243(3) 0.0448(12) Uani 1 1 d . . . C50 C 0.3983(4) 0.6845(4) 0.4326(3) 0.0452(13) Uani 1 1 d . . . C51 C 0.6028(4) 1.1291(4) 0.1803(4) 0.0484(13) Uani 1 1 d . . . C52 C 0.4549(5) 1.2260(4) 0.0876(4) 0.0516(14) Uani 1 1 d . . . C53 C 0.4168(4) 1.0934(4) 0.1663(3) 0.0411(12) Uani 1 1 d . . . C54 C 0.5721(5) 1.1269(4) 0.3089(3) 0.0502(14) Uani 1 1 d . . . H54A H 0.5271 1.1225 0.3396 0.060 Uiso 1 1 calc R . . C55 C 0.3769(5) 1.1595(4) 0.2047(3) 0.0453(13) Uani 1 1 d . . . C56 C 0.5338(4) 1.1189(4) 0.2241(3) 0.0443(12) Uani 1 1 d . . . C57 C 0.5458(5) 1.1231(4) 0.0929(3) 0.0451(13) Uani 1 1 d . . . C58 C -0.1180(6) 0.6669(4) 0.2094(5) 0.145(2) Uani 1 1 d D . . C59 C -0.1053(10) 0.5752(6) 0.2165(10) 0.145(2) Uani 1 1 d D . . C60 C 0.9013(12) 0.9604(11) 0.2095(10) 0.145(2) Uani 1 1 d D . . C61 C 0.9213(10) 1.0330(10) 0.1563(9) 0.145(2) Uani 1 1 d D A . F1 F -0.0948(8) 0.6962(7) 0.1471(5) 0.233(2) Uani 1 1 d D . . F2 F -0.0520(7) 0.7403(7) 0.2770(5) 0.233(2) Uani 1 1 d D . . F3 F -0.2200(6) 0.6477(7) 0.1975(6) 0.233(2) Uani 1 1 d D . . F4 F 0.856(3) 0.8702(18) 0.1711(15) 0.233(2) Uani 0.579(13) 1 d P A 1 F5 F 0.981(2) 0.9906(18) 0.2753(17) 0.233(2) Uani 0.579(13) 1 d P A 1 F6 F 0.805(2) 0.9465(18) 0.2226(15) 0.233(2) Uani 0.579(13) 1 d P A 1 F7 F 0.970(3) 0.920(2) 0.216(2) 0.233(2) Uani 0.421(13) 1 d P A 2 F8 F 0.924(3) 0.998(2) 0.286(2) 0.233(2) Uani 0.421(13) 1 d P A 2 F9 F 0.805(3) 0.888(3) 0.192(2) 0.233(2) Uani 0.421(13) 1 d P A 2 O1W O -0.0593(8) 0.7064(5) -0.1920(5) 0.162(3) Uani 1 1 d . . . H1E H -0.0194 0.6748 -0.2091 0.244 Uiso 1 1 d R . . H1F H -0.0128 0.7700 -0.1807 0.244 Uiso 1 1 d R . . O2W O 0.0654(17) 0.6126(14) -0.231(2) 0.53(2) Uani 1 1 d . . . H2E H 0.0357 0.5648 -0.2114 0.797 Uiso 1 1 d R . . H2F H 0.1225 0.6068 -0.2358 0.797 Uiso 1 1 d R . . O3W O -0.0133(6) 0.5783(5) 0.0380(5) 0.131(2) Uani 1 1 d . . . O4W O -0.0925(5) 0.7024(5) -0.0366(5) 0.136(3) Uani 1 1 d . . . H4E H -0.0666 0.6611 -0.0122 0.204 Uiso 1 1 d R . . H4F H -0.0816 0.7041 -0.0882 0.204 Uiso 1 1 d R . . O5W O 0.9595(5) 1.0937(4) -0.0310(4) 0.1078(19) Uani 1 1 d . . . H5E H 0.9588 1.0646 0.0098 0.162 Uiso 1 1 d R . . H5F H 0.9841 1.0578 -0.0640 0.162 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0672(10) 0.0461(8) 0.0606(9) 0.0166(7) 0.0210(8) 0.0344(8) S2 0.0596(10) 0.0432(8) 0.0648(10) 0.0125(7) 0.0215(8) 0.0169(7) N1 0.048(3) 0.048(3) 0.068(3) 0.021(2) 0.029(2) 0.023(2) N2 0.064(3) 0.038(2) 0.064(3) 0.014(2) 0.035(3) 0.024(2) O1 0.069(3) 0.081(3) 0.125(4) 0.055(3) 0.059(3) 0.050(3) O2 0.085(3) 0.094(4) 0.101(4) 0.055(3) 0.040(3) 0.063(3) O3 0.091(3) 0.054(3) 0.101(4) 0.027(2) 0.059(3) 0.027(3) O4 0.082(3) 0.062(3) 0.127(4) 0.032(3) 0.060(3) 0.044(3) O5 0.087(3) 0.063(3) 0.062(3) 0.016(2) 0.043(2) 0.029(3) O6 0.060(3) 0.057(2) 0.067(3) 0.015(2) 0.024(2) 0.037(2) O7 0.084(3) 0.070(3) 0.063(3) 0.027(2) 0.045(2) 0.045(3) O8 0.068(3) 0.048(2) 0.055(2) 0.001(2) 0.025(2) 0.026(2) O9 0.082(3) 0.045(2) 0.049(2) 0.0242(18) 0.030(2) 0.032(2) O10 0.089(3) 0.048(2) 0.059(3) 0.022(2) 0.038(2) 0.035(2) O11 0.202(9) 0.176(8) 0.168(7) 0.089(6) 0.100(7) 0.123(7) O12 0.281(13) 0.237(11) 0.232(11) 0.144(10) 0.191(11) 0.174(11) O13 0.140(6) 0.102(5) 0.179(7) 0.019(5) 0.071(5) 0.069(5) O14 0.122(5) 0.155(6) 0.118(5) 0.042(4) 0.062(4) 0.089(5) C1 0.093(6) 0.074(6) 0.171(10) 0.051(6) 0.047(7) 0.019(5) C2 0.096(6) 0.100(6) 0.057(5) 0.004(4) 0.007(4) 0.028(5) C3 0.102(6) 0.078(5) 0.147(8) 0.059(5) 0.087(6) 0.036(5) C4 0.119(6) 0.070(5) 0.127(7) 0.040(4) 0.055(5) 0.073(5) C5 0.199(11) 0.079(6) 0.183(10) 0.075(6) 0.128(9) 0.100(7) C6 0.067(5) 0.121(7) 0.209(11) 0.065(7) 0.070(6) 0.059(5) C7 0.102(6) 0.053(4) 0.103(6) -0.004(4) 0.037(5) 0.033(4) C8 0.092(6) 0.100(7) 0.064(5) -0.018(5) 0.022(5) 0.013(5) C9 0.084(5) 0.072(5) 0.101(6) 0.043(4) 0.058(5) 0.028(4) C10 0.086(5) 0.042(4) 0.112(6) 0.015(4) 0.038(5) 0.013(4) C11 0.082(5) 0.094(5) 0.115(6) 0.010(5) 0.039(4) 0.068(5) C12 0.055(4) 0.084(5) 0.088(5) 0.030(4) 0.013(4) 0.035(4) C13 0.070(4) 0.056(4) 0.062(4) 0.021(3) 0.033(3) 0.019(3) C14 0.149(8) 0.110(7) 0.118(7) 0.081(6) 0.081(7) 0.106(7) C15 0.073(5) 0.078(5) 0.114(6) 0.060(4) 0.051(4) 0.039(4) C16 0.073(5) 0.072(4) 0.054(4) 0.012(3) 0.013(4) 0.029(4) C17 0.090(6) 0.061(4) 0.075(5) 0.004(4) 0.041(5) 0.024(4) C18 0.069(5) 0.050(4) 0.085(5) 0.009(4) 0.008(4) 0.011(4) C19 0.056(4) 0.051(4) 0.104(6) 0.021(4) 0.019(4) 0.012(3) C20 0.073(4) 0.065(4) 0.059(4) 0.023(3) 0.032(3) 0.030(4) C21 0.126(6) 0.052(4) 0.067(4) 0.035(3) 0.039(4) 0.038(4) C22 0.141(7) 0.059(4) 0.094(5) 0.044(4) 0.077(6) 0.066(5) C23 0.059(4) 0.062(4) 0.071(4) 0.021(3) 0.032(3) 0.026(3) C24 0.051(4) 0.062(4) 0.089(5) 0.000(4) 0.015(4) 0.020(3) C25 0.064(4) 0.057(4) 0.060(4) 0.009(3) 0.015(3) 0.020(4) C26 0.060(4) 0.065(4) 0.053(4) 0.016(3) 0.007(3) 0.026(3) C27 0.113(6) 0.047(4) 0.086(5) 0.027(3) 0.046(5) 0.044(4) C28 0.093(5) 0.071(4) 0.064(4) 0.034(3) 0.033(4) 0.056(4) C29 0.053(4) 0.049(3) 0.083(5) 0.022(3) 0.029(3) 0.019(3) C30 0.077(4) 0.060(4) 0.042(3) 0.018(3) 0.019(3) 0.038(3) C31 0.090(5) 0.054(4) 0.066(4) 0.030(3) 0.035(4) 0.042(4) C32 0.052(4) 0.044(3) 0.080(4) 0.013(3) 0.026(3) 0.021(3) C33 0.073(4) 0.045(3) 0.065(4) 0.019(3) 0.032(4) 0.035(3) C34 0.050(3) 0.051(3) 0.087(5) 0.030(3) 0.032(3) 0.028(3) C35 0.062(4) 0.044(3) 0.046(3) 0.017(2) 0.025(3) 0.023(3) C36 0.080(5) 0.034(3) 0.075(4) 0.018(3) 0.045(4) 0.025(3) C37 0.061(4) 0.050(3) 0.057(4) 0.013(3) 0.029(3) 0.021(3) C39 0.066(4) 0.042(3) 0.082(5) 0.028(3) 0.049(4) 0.026(3) C40 0.049(3) 0.044(3) 0.054(3) 0.019(2) 0.023(3) 0.023(3) C41 0.051(3) 0.044(3) 0.058(4) 0.015(3) 0.019(3) 0.020(3) C42 0.063(4) 0.072(4) 0.067(4) 0.040(3) 0.029(3) 0.038(4) C43 0.058(3) 0.043(3) 0.046(3) 0.014(3) 0.020(3) 0.029(3) C44 0.046(3) 0.050(3) 0.063(4) 0.022(3) 0.022(3) 0.025(3) C45 0.050(3) 0.036(3) 0.049(3) 0.012(2) 0.018(3) 0.022(3) C46 0.047(3) 0.041(3) 0.049(3) 0.015(2) 0.018(3) 0.020(3) C47 0.064(4) 0.040(3) 0.046(3) 0.016(2) 0.025(3) 0.033(3) C48 0.049(3) 0.047(3) 0.055(3) 0.021(3) 0.027(3) 0.024(3) C49 0.052(3) 0.034(3) 0.049(3) 0.012(2) 0.019(3) 0.021(3) C50 0.050(3) 0.042(3) 0.044(3) 0.014(2) 0.020(3) 0.021(3) C51 0.048(3) 0.044(3) 0.059(3) 0.015(3) 0.023(3) 0.026(3) C52 0.072(4) 0.043(3) 0.055(3) 0.022(3) 0.029(3) 0.036(3) C53 0.044(3) 0.035(3) 0.046(3) 0.009(2) 0.017(2) 0.021(2) C54 0.058(4) 0.042(3) 0.051(3) 0.017(2) 0.019(3) 0.025(3) C55 0.051(3) 0.046(3) 0.051(3) 0.021(3) 0.028(3) 0.028(3) C56 0.053(3) 0.037(3) 0.045(3) 0.011(2) 0.020(3) 0.023(3) C57 0.062(3) 0.037(3) 0.049(3) 0.018(2) 0.029(3) 0.029(3) C58 0.101(4) 0.133(6) 0.169(6) 0.021(4) 0.033(4) 0.047(4) C59 0.101(4) 0.133(6) 0.169(6) 0.021(4) 0.033(4) 0.047(4) C60 0.101(4) 0.133(6) 0.169(6) 0.021(4) 0.033(4) 0.047(4) C61 0.101(4) 0.133(6) 0.169(6) 0.021(4) 0.033(4) 0.047(4) F1 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F2 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F3 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F4 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F5 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F6 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F7 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F8 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) F9 0.255(6) 0.207(5) 0.249(5) 0.096(4) 0.095(4) 0.114(5) O1W 0.205(9) 0.097(5) 0.161(7) 0.022(5) 0.057(6) 0.065(6) O2W 0.271(18) 0.254(18) 1.06(7) 0.28(3) 0.12(3) 0.179(16) O3W 0.138(6) 0.093(4) 0.166(7) 0.048(4) 0.076(5) 0.046(4) O4W 0.100(5) 0.117(5) 0.143(6) 0.012(4) 0.014(4) 0.039(4) O5W 0.126(5) 0.089(4) 0.126(5) 0.023(3) 0.046(4) 0.070(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C49 1.682(5) . ? S1 C33 1.721(6) . ? S2 C48 1.682(6) . ? S2 C29 1.709(7) . ? N1 C48 1.327(7) . ? N1 C34 1.410(8) . ? N1 C20 1.470(8) . ? N2 C49 1.333(7) . ? N2 C36 1.391(7) . ? N2 C24 1.467(8) . ? O1 C32 1.316(8) . ? O1 C6 1.462(8) . ? O2 C32 1.201(8) . ? O3 C44 1.317(7) . ? O3 C3 1.447(9) . ? O4 C39 1.227(7) . ? O5 C44 1.203(7) . ? O6 C55 1.317(7) . ? O6 C11 1.478(7) . ? O7 C57 1.198(6) . ? O8 C55 1.194(6) . ? O9 C43 1.309(7) . ? O9 C21 1.437(7) . ? O10 C43 1.230(6) . ? O11 C59 1.304(15) . ? O12 C59 1.213(16) . ? O13 C61 1.226(15) . ? O14 C61 1.216(15) . ? C1 C19 1.498(11) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C16 1.397(10) . ? C2 C8 1.397(13) . ? C2 H2A 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C33 1.505(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C22 1.519(9) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C36 1.500(9) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C17 1.340(12) . ? C8 H8A 0.9300 . ? C9 C19 1.358(10) . ? C9 C13 1.417(10) . ? C9 H9A 0.9300 . ? C10 C29 1.509(9) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C23 1.373(9) . ? C12 C26 1.398(10) . ? C12 H12A 0.9300 . ? C13 C41 1.367(8) . ? C13 H13A 0.9300 . ? C14 C22 1.371(12) . ? C14 C28 1.410(10) . ? C14 H14A 0.9300 . ? C15 C34 1.481(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C35 1.384(9) . ? C16 H16A 0.9300 . ? C17 C37 1.398(9) . ? C17 H17A 0.9300 . ? C18 C19 1.374(11) . ? C18 C25 1.395(10) . ? C18 H18A 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C27 1.375(11) . ? C23 C51 1.375(8) . ? C23 H23A 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C41 1.404(8) . ? C25 H25A 0.9300 . ? C26 C54 1.356(8) . ? C26 H26A 0.9300 . ? C27 C31 1.384(8) . ? C27 H27A 0.9300 . ? C28 C52 1.377(8) . ? C28 H28A 0.9300 . ? C29 C34 1.324(9) . ? C30 C47 1.509(8) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C52 1.393(9) . ? C31 H31A 0.9300 . ? C32 C46 1.525(8) . ? C33 C36 1.316(9) . ? C35 C37 1.401(8) . ? C35 C50 1.507(7) . ? C37 C39 1.433(9) . ? C39 C40 1.526(8) . ? C40 C42 1.500(8) . ? C40 C41 1.550(8) . ? C40 C50 1.620(7) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 C50 1.513(7) . ? C44 C45 1.498(8) . ? C45 C49 1.509(7) . ? C45 C53 1.566(7) . ? C45 H45A 0.9800 . ? C46 C48 1.497(7) . ? C46 C50 1.575(7) . ? C46 H46A 0.9800 . ? C47 C52 1.535(7) . ? C47 C57 1.535(8) . ? C47 C53 1.601(7) . ? C51 C56 1.374(7) . ? C51 C57 1.479(8) . ? C53 C56 1.531(7) . ? C53 C55 1.542(7) . ? C54 C56 1.388(8) . ? C54 H54A 0.9300 . ? C58 F3 1.300(11) . ? C58 F1 1.301(11) . ? C58 F2 1.301(13) . ? C58 C59 1.540(11) . ? C60 F5 1.22(3) . ? C60 F9 1.26(4) . ? C60 F4 1.26(2) . ? C60 F8 1.27(4) . ? C60 F7 1.36(3) . ? C60 F6 1.39(3) . ? C60 C61 1.540(11) . ? O1W H1E 0.9770 . ? O1W H1F 0.8841 . ? O2W H2E 0.8589 . ? O2W H2F 0.8798 . ? O4W H4E 0.9618 . ? O4W H4F 0.9542 . ? O5W H5E 0.8908 . ? O5W H5F 0.9834 . ? 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 C49 S1 C33 92.2(3) . . ? C48 S2 C29 92.0(3) . . ? C48 N1 C34 113.8(5) . . ? C48 N1 C20 125.1(5) . . ? C34 N1 C20 121.1(5) . . ? C49 N2 C36 114.4(5) . . ? C49 N2 C24 125.2(5) . . ? C36 N2 C24 120.4(5) . . ? C32 O1 C6 118.9(6) . . ? C44 O3 C3 118.5(5) . . ? C55 O6 C11 116.3(5) . . ? C43 O9 C21 115.7(4) . . ? C19 C1 H1A 109.5 . . ? C19 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C19 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C16 C2 C8 121.5(8) . . ? C16 C2 H2A 119.2 . . ? C8 C2 H2A 119.2 . . ? O3 C3 H3A 109.5 . . ? O3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C33 C4 H4A 109.5 . . ? C33 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C33 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C22 C5 H5A 109.5 . . ? C22 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C22 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 C6 H6A 109.5 . . ? O1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C36 C7 H7A 109.5 . . ? C36 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C36 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C17 C8 C2 121.3(7) . . ? C17 C8 H8A 119.3 . . ? C2 C8 H8A 119.3 . . ? C19 C9 C13 121.5(7) . . ? C19 C9 H9A 119.2 . . ? C13 C9 H9A 119.2 . . ? C29 C10 H10A 109.5 . . ? C29 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C29 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O6 C11 H11A 109.5 . . ? O6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C23 C12 C26 119.7(6) . . ? C23 C12 H12A 120.2 . . ? C26 C12 H12A 120.2 . . ? C41 C13 C9 120.7(6) . . ? C41 C13 H13A 119.7 . . ? C9 C13 H13A 119.7 . . ? C22 C14 C28 123.0(7) . . ? C22 C14 H14A 118.5 . . ? C28 C14 H14A 118.5 . . ? C34 C15 H15A 109.5 . . ? C34 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C34 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C35 C16 C2 117.6(7) . . ? C35 C16 H16A 121.2 . . ? C2 C16 H16A 121.2 . . ? C8 C17 C37 118.0(7) . . ? C8 C17 H17A 121.0 . . ? C37 C17 H17A 121.0 . . ? C19 C18 C25 122.3(7) . . ? C19 C18 H18A 118.9 . . ? C25 C18 H18A 118.9 . . ? C9 C19 C18 117.7(7) . . ? C9 C19 C1 119.9(9) . . ? C18 C19 C1 122.4(8) . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O9 C21 H21A 109.5 . . ? O9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C14 C22 C27 117.5(6) . . ? C14 C22 C5 120.4(8) . . ? C27 C22 C5 122.1(9) . . ? C12 C23 C51 118.4(6) . . ? C12 C23 H23A 120.8 . . ? C51 C23 H23A 120.8 . . ? N2 C24 H24A 109.5 . . ? N2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C18 C25 C41 119.7(7) . . ? C18 C25 H25A 120.1 . . ? C41 C25 H25A 120.1 . . ? C54 C26 C12 121.9(6) . . ? C54 C26 H26A 119.0 . . ? C12 C26 H26A 119.0 . . ? C22 C27 C31 120.2(8) . . ? C22 C27 H27A 119.9 . . ? C31 C27 H27A 119.9 . . ? C52 C28 C14 119.1(8) . . ? C52 C28 H28A 120.5 . . ? C14 C28 H28A 120.5 . . ? C34 C29 C10 128.4(7) . . ? C34 C29 S2 111.3(5) . . ? C10 C29 S2 120.3(6) . . ? C47 C30 H30A 109.5 . . ? C47 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C47 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 C52 122.7(7) . . ? C27 C31 H31A 118.7 . . ? C52 C31 H31A 118.7 . . ? O2 C32 O1 124.2(6) . . ? O2 C32 C46 125.9(6) . . ? O1 C32 C46 109.9(5) . . ? C36 C33 C4 130.5(6) . . ? C36 C33 S1 110.5(4) . . ? C4 C33 S1 118.9(5) . . ? C29 C34 N1 111.9(6) . . ? C29 C34 C15 127.8(6) . . ? N1 C34 C15 120.2(6) . . ? C16 C35 C37 119.6(5) . . ? C16 C35 C50 129.1(5) . . ? C37 C35 C50 111.3(5) . . ? C33 C36 N2 112.8(5) . . ? C33 C36 C7 126.3(6) . . ? N2 C36 C7 120.9(6) . . ? C17 C37 C35 122.0(6) . . ? C17 C37 C39 127.9(6) . . ? C35 C37 C39 110.2(5) . . ? O4 C39 C37 128.1(6) . . ? O4 C39 C40 121.4(6) . . ? C37 C39 C40 110.5(5) . . ? C42 C40 C39 109.9(5) . . ? C42 C40 C41 110.3(5) . . ? C39 C40 C41 107.1(4) . . ? C42 C40 C50 116.3(4) . . ? C39 C40 C50 102.0(4) . . ? C41 C40 C50 110.7(4) . . ? C13 C41 C25 118.1(6) . . ? C13 C41 C40 122.1(5) . . ? C25 C41 C40 119.8(5) . . ? C40 C42 H42A 109.5 . . ? C40 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C40 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O10 C43 O9 123.8(5) . . ? O10 C43 C50 122.5(5) . . ? O9 C43 C50 113.6(4) . . ? O5 C44 O3 122.8(6) . . ? O5 C44 C45 126.1(5) . . ? O3 C44 C45 111.1(5) . . ? C44 C45 C49 107.8(4) . . ? C44 C45 C53 113.8(4) . . ? C49 C45 C53 116.2(4) . . ? C44 C45 H45A 106.1 . . ? C49 C45 H45A 106.1 . . ? C53 C45 H45A 106.1 . . ? C48 C46 C32 108.9(5) . . ? C48 C46 C50 117.0(4) . . ? C32 C46 C50 112.3(5) . . ? C48 C46 H46A 105.9 . . ? C32 C46 H46A 105.9 . . ? C50 C46 H46A 105.9 . . ? C30 C47 C52 110.5(5) . . ? C30 C47 C57 110.5(4) . . ? C52 C47 C57 106.6(5) . . ? C30 C47 C53 115.4(5) . . ? C52 C47 C53 110.9(4) . . ? C57 C47 C53 102.2(4) . . ? N1 C48 C46 123.5(5) . . ? N1 C48 S2 111.0(4) . . ? C46 C48 S2 124.7(4) . . ? N2 C49 C45 124.1(5) . . ? N2 C49 S1 110.1(4) . . ? C45 C49 S1 124.9(4) . . ? C35 C50 C43 114.5(5) . . ? C35 C50 C46 113.1(4) . . ? C43 C50 C46 105.7(4) . . ? C35 C50 C40 103.6(4) . . ? C43 C50 C40 107.8(4) . . ? C46 C50 C40 112.2(4) . . ? C56 C51 C23 121.6(5) . . ? C56 C51 C57 110.3(5) . . ? C23 C51 C57 128.0(5) . . ? C28 C52 C31 117.5(5) . . ? C28 C52 C47 120.8(6) . . ? C31 C52 C47 121.7(5) . . ? C56 C53 C55 110.6(4) . . ? C56 C53 C45 112.3(4) . . ? C55 C53 C45 108.4(4) . . ? C56 C53 C47 103.7(4) . . ? C55 C53 C47 108.3(4) . . ? C45 C53 C47 113.4(4) . . ? C26 C54 C56 118.0(6) . . ? C26 C54 H54A 121.0 . . ? C56 C54 H54A 121.0 . . ? O8 C55 O6 125.3(5) . . ? O8 C55 C53 124.6(5) . . ? O6 C55 C53 110.0(4) . . ? C51 C56 C54 120.3(5) . . ? C51 C56 C53 111.0(5) . . ? C54 C56 C53 128.6(5) . . ? O7 C57 C51 126.3(5) . . ? O7 C57 C47 124.9(5) . . ? C51 C57 C47 108.8(4) . . ? F3 C58 F1 107.7(12) . . ? F3 C58 F2 107.6(12) . . ? F1 C58 F2 107.6(12) . . ? F3 C58 C59 110.6(8) . . ? F1 C58 C59 111.4(9) . . ? F2 C58 C59 111.6(8) . . ? O12 C59 O11 126.4(8) . . ? O12 C59 C58 112.6(12) . . ? O11 C59 C58 119.1(12) . . ? F4 C60 F6 91.5(17) . . ? F5 C60 F6 112.0(19) . . ? F5 C60 F4 116.0(19) . . ? F9 C60 F8 100(2) . . ? F9 C60 F7 105(2) . . ? F8 C60 F7 101(2) . . ? F9 C60 C61 121.1(18) . . ? F4 C60 C61 116.6(16) . . ? F8 C60 C61 115.3(19) . . ? F7 C60 C61 112.4(17) . . ? F6 C60 C61 105.9(14) . . ? F5 C60 C61 112.4(16) . . ? O14 C61 O13 131.9(14) . . ? O14 C61 C60 114.0(14) . . ? O13 C61 C60 114.0(14) . . ? H1E O1W H1F 103.6 . . ? H2E O2W H2F 101.5 . . ? H4E O4W H4F 109.3 . . ? H5E O5W H5F 99.2 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.671 _refine_diff_density_min -1.334 _refine_diff_density_rms 0.109 # Attachment '9b.cif' data_9b _database_code_depnum_ccdc_archive 'CCDC 653552' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H31 N O5 S' _chemical_formula_sum 'C29 H31 N O5 S' _chemical_formula_weight 505.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.0846(18) _cell_length_b 11.400(2) _cell_length_c 13.728(3) _cell_angle_alpha 89.60(3) _cell_angle_beta 77.09(3) _cell_angle_gamma 72.33(3) _cell_volume 1317.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2785 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 24.6 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID IP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 9633 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.24 _reflns_number_total 4525 _reflns_number_gt 3421 _reflns_threshold_expression I>2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0597P)^2^+0.2991P] 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 4525 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.05908(7) 0.64064(6) 0.37786(5) 0.0430(2) Uani 1 1 d . . . O1 O 0.10198(16) 0.38077(15) 0.23919(12) 0.0410(4) Uani 1 1 d . . . O5 O 0.45649(17) 0.64342(14) 0.20034(14) 0.0445(4) Uani 1 1 d . . . O4 O 0.61325(16) 0.44768(14) 0.20590(13) 0.0404(4) Uani 1 1 d . . . O2 O 0.10357(18) 0.32936(16) 0.39662(13) 0.0461(4) Uani 1 1 d . . . O3 O 0.73631(19) 0.15697(16) 0.22068(15) 0.0559(5) Uani 1 1 d . . . N N 0.1346(2) 0.66707(16) 0.19418(14) 0.0344(4) Uani 1 1 d . . . C11 C 0.3360(2) 0.36910(19) 0.29327(16) 0.0290(5) Uani 1 1 d . . . C8 C 0.3344(2) 0.49250(18) 0.24782(15) 0.0283(5) Uani 1 1 d . . . C1 C 0.1891(2) 0.59294(19) 0.26332(16) 0.0306(5) Uani 1 1 d . . . C21 C 0.4529(2) 0.24705(19) 0.22336(17) 0.0326(5) Uani 1 1 d . . . C20 C 0.6047(3) 0.2220(2) 0.26365(19) 0.0377(5) Uani 1 1 d . . . C9 C 0.4784(2) 0.51947(19) 0.21653(16) 0.0314(5) Uani 1 1 d . . . C19 C 0.5609(2) 0.2801(2) 0.36478(18) 0.0361(5) Uani 1 1 d . . . C12 C 0.1680(2) 0.35694(19) 0.31810(17) 0.0323(5) Uani 1 1 d . . . C15 C 0.3346(3) 0.4136(2) 0.48115(17) 0.0389(5) Uani 1 1 d . . . H15 H 0.2300 0.4650 0.4965 0.047 Uiso 1 1 calc R . . C14 C 0.4040(2) 0.35555(19) 0.38617(16) 0.0314(5) Uani 1 1 d . . . C29 C 0.3865(3) 0.1383(2) 0.24952(18) 0.0382(5) Uani 1 1 d . . . C5 C -0.0081(3) 0.7626(2) 0.2308(2) 0.0410(6) Uani 1 1 d . . . C6 C -0.0658(3) 0.7594(2) 0.3289(2) 0.0449(6) Uani 1 1 d . . . C10 C 0.5954(3) 0.6803(2) 0.1719(2) 0.0529(7) Uani 1 1 d . . . H10A H 0.6623 0.6507 0.2177 0.079 Uiso 1 1 calc R . . H10B H 0.5659 0.7687 0.1734 0.079 Uiso 1 1 calc R . . H10C H 0.6519 0.6464 0.1054 0.079 Uiso 1 1 calc R . . C3 C 0.2077(3) 0.6404(3) 0.08627(18) 0.0454(6) Uani 1 1 d . . . H3A H 0.3166 0.5876 0.0773 0.054 Uiso 1 1 calc R . . H3B H 0.2097 0.7169 0.0554 0.054 Uiso 1 1 calc R . . C16 C 0.4240(3) 0.3934(2) 0.5524(2) 0.0467(6) Uani 1 1 d . . . H16 H 0.3777 0.4307 0.6166 0.056 Uiso 1 1 calc R . . C27 C 0.4822(3) 0.2645(2) 0.11050(17) 0.0406(6) Uani 1 1 d . . . H27A H 0.3802 0.2947 0.0929 0.049 Uiso 1 1 calc R . . H27B H 0.5340 0.3276 0.0964 0.049 Uiso 1 1 calc R . . C26 C 0.2836(3) 0.1126(3) 0.1973(2) 0.0557(7) Uani 1 1 d . . . H26 H 0.2605 0.1580 0.1430 0.067 Uiso 1 1 calc R . . C4 C -0.0793(4) 0.8552(2) 0.1626(3) 0.0659(8) Uani 1 1 d . . . H4A H -0.1353 0.8201 0.1254 0.099 Uiso 1 1 calc R . . H4B H 0.0036 0.8771 0.1171 0.099 Uiso 1 1 calc R . . H4C H -0.1518 0.9275 0.2018 0.099 Uiso 1 1 calc R . . C18 C 0.6504(3) 0.2615(2) 0.4370(2) 0.0459(6) Uani 1 1 d . . . H18 H 0.7555 0.2110 0.4221 0.055 Uiso 1 1 calc R . . C2 C 0.1190(4) 0.5783(3) 0.0350(2) 0.0726(9) Uani 1 1 d . . . H2A H 0.1190 0.5016 0.0643 0.109 Uiso 1 1 calc R . . H2B H 0.1697 0.5628 -0.0350 0.109 Uiso 1 1 calc R . . H2C H 0.0115 0.6308 0.0429 0.109 Uiso 1 1 calc R . . C17 C 0.5801(3) 0.3193(2) 0.5309(2) 0.0517(7) Uani 1 1 d . . . H17 H 0.6381 0.3083 0.5800 0.062 Uiso 1 1 calc R . . C23 C 0.3532(4) -0.0275(3) 0.3544(3) 0.0691(9) Uani 1 1 d . . . H23 H 0.3782 -0.0750 0.4072 0.083 Uiso 1 1 calc R . . C22 C 0.4197(3) 0.0647(2) 0.3281(2) 0.0506(7) Uani 1 1 d . . . H22 H 0.4891 0.0785 0.3639 0.061 Uiso 1 1 calc R . . C24 C 0.2501(4) -0.0500(3) 0.3032(3) 0.0768(10) Uani 1 1 d . . . H24 H 0.2044 -0.1121 0.3213 0.092 Uiso 1 1 calc R . . C28 C 0.5829(4) 0.1487(3) 0.0432(2) 0.0629(8) Uani 1 1 d . . . H28A H 0.6861 0.1198 0.0576 0.094 Uiso 1 1 calc R . . H28B H 0.5935 0.1679 -0.0257 0.094 Uiso 1 1 calc R . . H28C H 0.5322 0.0856 0.0555 0.094 Uiso 1 1 calc R . . C7 C -0.2130(3) 0.8459(3) 0.3956(3) 0.0722(9) Uani 1 1 d . . . H7A H -0.2266 0.9285 0.3754 0.108 Uiso 1 1 calc R . . H7B H -0.2028 0.8422 0.4638 0.108 Uiso 1 1 calc R . . H7C H -0.3037 0.8220 0.3902 0.108 Uiso 1 1 calc R . . C13 C -0.0559(3) 0.3688(3) 0.2534(2) 0.0685(9) Uani 1 1 d . . . H13A H -0.0497 0.2835 0.2588 0.103 Uiso 1 1 calc R . . H13B H -0.0994 0.3994 0.1972 0.103 Uiso 1 1 calc R . . H13C H -0.1230 0.4156 0.3135 0.103 Uiso 1 1 calc R . . C25 C 0.2153(4) 0.0204(3) 0.2249(3) 0.0747(10) Uani 1 1 d . . . H25 H 0.1451 0.0060 0.1900 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0366(3) 0.0421(3) 0.0395(4) -0.0015(3) -0.0003(2) -0.0026(3) O1 0.0308(8) 0.0566(10) 0.0429(10) 0.0084(8) -0.0135(7) -0.0207(8) O5 0.0344(8) 0.0342(8) 0.0685(12) 0.0104(8) -0.0119(8) -0.0162(7) O4 0.0234(8) 0.0409(9) 0.0537(11) 0.0041(7) -0.0063(7) -0.0073(7) O2 0.0422(9) 0.0576(11) 0.0396(10) 0.0059(8) -0.0012(7) -0.0231(8) O3 0.0339(9) 0.0459(10) 0.0786(14) -0.0076(9) -0.0103(9) -0.0003(8) N 0.0297(9) 0.0333(10) 0.0412(11) 0.0053(8) -0.0110(8) -0.0091(8) C11 0.0266(10) 0.0298(11) 0.0307(12) 0.0026(9) -0.0055(8) -0.0095(9) C8 0.0238(10) 0.0292(10) 0.0313(12) 0.0022(9) -0.0073(8) -0.0069(9) C1 0.0272(11) 0.0288(10) 0.0362(13) 0.0007(9) -0.0065(9) -0.0101(9) C21 0.0306(11) 0.0292(11) 0.0372(13) 0.0002(9) -0.0057(9) -0.0097(9) C20 0.0315(12) 0.0275(11) 0.0534(15) 0.0052(10) -0.0103(10) -0.0077(10) C9 0.0322(12) 0.0311(11) 0.0318(12) 0.0026(9) -0.0070(9) -0.0115(10) C19 0.0349(12) 0.0314(11) 0.0470(14) 0.0080(10) -0.0154(10) -0.0132(10) C12 0.0316(11) 0.0304(11) 0.0343(13) -0.0002(9) -0.0061(9) -0.0101(9) C15 0.0468(13) 0.0368(12) 0.0369(13) 0.0057(10) -0.0129(10) -0.0165(11) C14 0.0362(12) 0.0276(10) 0.0360(13) 0.0070(9) -0.0124(9) -0.0152(9) C29 0.0359(12) 0.0286(11) 0.0477(15) -0.0038(10) -0.0037(10) -0.0109(10) C5 0.0310(12) 0.0288(11) 0.0645(18) 0.0040(11) -0.0172(11) -0.0065(10) C6 0.0338(12) 0.0338(12) 0.0608(18) -0.0025(11) -0.0067(11) -0.0044(10) C10 0.0513(15) 0.0515(15) 0.0634(18) 0.0140(13) -0.0095(12) -0.0299(13) C3 0.0459(14) 0.0544(15) 0.0376(14) 0.0143(11) -0.0108(11) -0.0176(12) C16 0.0660(17) 0.0449(13) 0.0398(15) 0.0093(11) -0.0206(12) -0.0268(13) C27 0.0422(13) 0.0383(12) 0.0377(14) -0.0041(10) -0.0020(10) -0.0123(11) C26 0.0624(17) 0.0537(16) 0.0592(18) -0.0020(13) -0.0147(13) -0.0291(14) C4 0.0612(18) 0.0437(15) 0.090(2) 0.0164(15) -0.0323(16) -0.0026(14) C18 0.0439(14) 0.0406(13) 0.0640(18) 0.0181(12) -0.0277(12) -0.0181(11) C2 0.077(2) 0.098(2) 0.0468(18) -0.0080(17) -0.0188(15) -0.0286(19) C17 0.0733(19) 0.0474(14) 0.0553(18) 0.0186(13) -0.0381(14) -0.0325(14) C23 0.081(2) 0.0397(15) 0.090(3) 0.0180(15) -0.0182(18) -0.0252(15) C22 0.0563(16) 0.0299(12) 0.0658(19) 0.0070(12) -0.0126(13) -0.0147(12) C24 0.084(2) 0.0463(17) 0.107(3) 0.0058(18) -0.010(2) -0.0397(17) C28 0.0725(19) 0.0574(17) 0.0481(17) -0.0149(14) 0.0071(14) -0.0193(15) C7 0.0494(17) 0.0527(17) 0.090(3) -0.0067(16) 0.0050(15) 0.0053(14) C13 0.0362(14) 0.104(3) 0.076(2) 0.0094(18) -0.0183(13) -0.0336(16) C25 0.076(2) 0.066(2) 0.099(3) -0.009(2) -0.0195(19) -0.0472(18) _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 S C1 1.719(2) . ? S C6 1.722(3) . ? O1 C12 1.340(3) . ? O1 C13 1.451(3) . ? O5 C9 1.389(3) . ? O5 C10 1.422(3) . ? O4 C9 1.227(2) . ? O2 C12 1.195(3) . ? O3 C20 1.216(3) . ? N C1 1.343(3) . ? N C5 1.407(3) . ? N C3 1.474(3) . ? C11 C14 1.524(3) . ? C11 C8 1.532(3) . ? C11 C12 1.536(3) . ? C11 C21 1.628(3) . ? C8 C9 1.408(3) . ? C8 C1 1.435(3) . ? C21 C27 1.534(3) . ? C21 C29 1.543(3) . ? C21 C20 1.546(3) . ? C20 C19 1.460(3) . ? C19 C14 1.389(3) . ? C19 C18 1.394(3) . ? C15 C16 1.381(3) . ? C15 C14 1.388(3) . ? C15 H15 0.9300 . ? C29 C22 1.392(4) . ? C29 C26 1.394(4) . ? C5 C6 1.336(4) . ? C5 C4 1.499(4) . ? C6 C7 1.505(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C3 C2 1.501(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C27 C28 1.530(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C26 C25 1.385(4) . ? C26 H26 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C18 C17 1.375(4) . ? C18 H18 0.9300 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C17 H17 0.9300 . ? C23 C24 1.371(5) . ? C23 C22 1.372(4) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? C24 C25 1.373(5) . ? C24 H24 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C25 H25 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S C6 92.67(12) . . ? C12 O1 C13 115.6(2) . . ? C9 O5 C10 116.96(18) . . ? C1 N C5 115.19(19) . . ? C1 N C3 122.12(18) . . ? C5 N C3 122.2(2) . . ? C14 C11 C8 110.95(17) . . ? C14 C11 C12 110.75(17) . . ? C8 C11 C12 110.41(16) . . ? C14 C11 C21 101.74(16) . . ? C8 C11 C21 115.21(17) . . ? C12 C11 C21 107.44(16) . . ? C9 C8 C1 118.01(19) . . ? C9 C8 C11 119.19(17) . . ? C1 C8 C11 120.30(17) . . ? N C1 C8 126.9(2) . . ? N C1 S 108.97(15) . . ? C8 C1 S 124.06(17) . . ? C27 C21 C29 111.19(19) . . ? C27 C21 C20 113.03(18) . . ? C29 C21 C20 107.43(18) . . ? C27 C21 C11 114.44(17) . . ? C29 C21 C11 108.91(16) . . ? C20 C21 C11 101.21(17) . . ? O3 C20 C19 126.0(2) . . ? O3 C20 C21 125.2(2) . . ? C19 C20 C21 108.58(17) . . ? O4 C9 O5 119.80(18) . . ? O4 C9 C8 127.2(2) . . ? O5 C9 C8 112.92(18) . . ? C14 C19 C18 121.2(2) . . ? C14 C19 C20 110.09(19) . . ? C18 C19 C20 128.5(2) . . ? O2 C12 O1 123.8(2) . . ? O2 C12 C11 125.3(2) . . ? O1 C12 C11 110.88(18) . . ? C16 C15 C14 118.7(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C14 C19 119.6(2) . . ? C15 C14 C11 128.96(19) . . ? C19 C14 C11 111.28(19) . . ? C22 C29 C26 116.6(2) . . ? C22 C29 C21 122.5(2) . . ? C26 C29 C21 120.8(2) . . ? C6 C5 N 112.4(2) . . ? C6 C5 C4 126.6(2) . . ? N C5 C4 120.9(2) . . ? C5 C6 C7 128.6(2) . . ? C5 C6 S 110.71(17) . . ? C7 C6 S 120.6(2) . . ? O5 C10 H10A 109.5 . . ? O5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N C3 C2 111.9(2) . . ? N C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? N C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C17 C16 C15 121.7(2) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C28 C27 C21 115.3(2) . . ? C28 C27 H27A 108.5 . . ? C21 C27 H27A 108.5 . . ? C28 C27 H27B 108.5 . . ? C21 C27 H27B 108.5 . . ? H27A C27 H27B 107.5 . . ? C25 C26 C29 121.0(3) . . ? C25 C26 H26 119.5 . . ? C29 C26 H26 119.5 . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C5 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C17 C18 C19 118.6(2) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C22 C29 122.1(3) . . ? C23 C22 H22 118.9 . . ? C29 C22 H22 118.9 . . ? C23 C24 C25 119.1(3) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C24 C25 C26 120.8(3) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.238 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.048 data_13b _database_code_depnum_ccdc_archive 'CCDC 682292' _publ_section_comment ; The bond lengths C(58)-C(59) and C(63)-C(64) are too short due to the impossibility of modelling disorder or restraining the geometry in these groups. The large difference between the maxium and minumum Ueq for carbon atoms is due to disorder in the structure that could not be modelled and attempts to restrain the displacement parameters using DELU and/or SIMU failed. The solvent molecules O(1)-C(81)-C(82), O(1W) and O(2W) have been refined with isotropic displacement parameters due to disorder in these group which cannot be modelled. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32.50 H38.50 Br N O5.75 S' _chemical_formula_weight 647.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 26.9107(11) _cell_length_b 10.0719(3) _cell_length_c 27.6693(10) _cell_angle_alpha 90.00 _cell_angle_beta 116.8800(10) _cell_angle_gamma 90.00 _cell_volume 6689.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(1) _cell_measurement_reflns_used 29380 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2700.00 _exptl_absorpt_coefficient_mu 1.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.465 _exptl_absorpt_correction_T_max 0.766 # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46569 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0484 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.20 _reflns_number_total 11340 _reflns_number_gt 6309 _reflns_threshold_expression >2sigma(I) _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^)+(0.1435P)^2^] 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 11340 _refine_ls_number_parameters 746 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1307 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.2164 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.06636(3) 1.04021(9) 0.07801(3) 0.1187(3) Uani 1 1 d . . . Br2 Br 0.41316(4) 0.12382(10) 0.40911(4) 0.1356(4) Uani 1 1 d . . . S1 S 0.12276(6) 0.10641(13) 0.29381(6) 0.0739(4) Uani 1 1 d . . . S2 S 0.37343(6) 1.05849(15) 0.17793(6) 0.0850(5) Uani 1 1 d . . . N11 N 0.06434(16) 0.3578(4) 0.24042(15) 0.0661(11) Uani 1 1 d . . . N41 N 0.43014(16) 0.8149(5) 0.24389(16) 0.0753(12) Uani 1 1 d . . . O11 O 0.16420(11) 0.4242(3) 0.32883(11) 0.0540(7) Uani 1 1 d . . . O12 O 0.22173(16) 0.6274(4) 0.28739(15) 0.0874(11) Uani 1 1 d . . . O13 O 0.25507(14) 0.6862(4) 0.40515(14) 0.0772(10) Uani 1 1 d . . . O14 O 0.27527(14) 0.4751(4) 0.39500(14) 0.0725(9) Uani 1 1 d . . . O15 O 0.02500(14) 0.3465(4) 0.29735(14) 0.0795(10) Uani 1 1 d . . . O41 O 0.33411(12) 0.7427(3) 0.15262(13) 0.0654(9) Uani 1 1 d . . . O42 O 0.27392(16) 0.5567(4) 0.20144(16) 0.0968(13) Uani 1 1 d . . . O43 O 0.24154(15) 0.4749(4) 0.08985(16) 0.0898(12) Uani 1 1 d . . . O44 O 0.22442(15) 0.6923(4) 0.08550(18) 0.0975(13) Uani 1 1 d . . . O45 O 0.47629(14) 0.8017(4) 0.19355(14) 0.0817(10) Uani 1 1 d . . . C1 C 0.17896(18) 0.5489(4) 0.35648(17) 0.0530(11) Uani 1 1 d . . . C2 C 0.15530(18) 0.5425(4) 0.39641(17) 0.0536(11) Uani 1 1 d . . . C3 C 0.1622(2) 0.6299(5) 0.43791(18) 0.0631(12) Uani 1 1 d . . . H3 H 0.1860 0.7024 0.4457 0.076 Uiso 1 1 calc R . . C4 C 0.1335(2) 0.6074(5) 0.4670(2) 0.0741(15) Uani 1 1 d . . . H4 H 0.1385 0.6632 0.4956 0.089 Uiso 1 1 calc R . . C5 C 0.0972(2) 0.5022(6) 0.4540(2) 0.0751(15) Uani 1 1 d . . . H5 H 0.0769 0.4900 0.4734 0.090 Uiso 1 1 calc R . . C6 C 0.0899(2) 0.4145(5) 0.41322(19) 0.0651(13) Uani 1 1 d . . . H6 H 0.0645 0.3451 0.4044 0.078 Uiso 1 1 calc R . . C7 C 0.12139(18) 0.4322(4) 0.38563(17) 0.0548(11) Uani 1 1 d . . . C8 C 0.12475(18) 0.3517(4) 0.34078(17) 0.0535(11) Uani 1 1 d . . . C9 C 0.15172(19) 0.6601(5) 0.31507(18) 0.0571(11) Uani 1 1 d . . . H9A H 0.1123 0.6409 0.2943 0.069 Uiso 1 1 calc R . . H9B H 0.1552 0.7428 0.3343 0.069 Uiso 1 1 calc R . . C10 C 0.1767(2) 0.6779(5) 0.27656(19) 0.0625(12) Uani 1 1 d . . . C11 C 0.14749(19) 0.7612(5) 0.22747(17) 0.0568(11) Uani 1 1 d . . . C12 C 0.09824(19) 0.8252(5) 0.21527(18) 0.0607(12) Uani 1 1 d . . . H12 H 0.0814 0.8147 0.2379 0.073 Uiso 1 1 calc R . . C13 C 0.0731(2) 0.9052(5) 0.16997(19) 0.0672(13) Uani 1 1 d . . . H13 H 0.0397 0.9479 0.1620 0.081 Uiso 1 1 calc R . . C14 C 0.0982(2) 0.9203(5) 0.13720(19) 0.0710(14) Uani 1 1 d . . . C15 C 0.1474(2) 0.8551(6) 0.1473(2) 0.0760(15) Uani 1 1 d . . . H15 H 0.1636 0.8650 0.1241 0.091 Uiso 1 1 calc R . . C16 C 0.1717(2) 0.7752(5) 0.1926(2) 0.0695(13) Uani 1 1 d . . . H16 H 0.2045 0.7302 0.1999 0.083 Uiso 1 1 calc R . . C17 C 0.2427(2) 0.5609(6) 0.38655(19) 0.0619(12) Uani 1 1 d . . . C18 C 0.3136(2) 0.7181(7) 0.4356(3) 0.0954(19) Uani 1 1 d . . . H18A H 0.3346 0.6379 0.4515 0.115 Uiso 1 1 calc R . . H18B H 0.3189 0.7790 0.4647 0.115 Uiso 1 1 calc R . . C19 C 0.3336(3) 0.7785(8) 0.3998(3) 0.121(3) Uani 1 1 d . . . H19A H 0.3320 0.7146 0.3734 0.181 Uiso 1 1 calc R . . H19B H 0.3714 0.8073 0.4208 0.181 Uiso 1 1 calc R . . H19C H 0.3107 0.8534 0.3818 0.181 Uiso 1 1 calc R . . C20 C 0.14658(18) 0.2046(4) 0.35658(18) 0.0589(12) Uani 1 1 d . . . C21 C 0.20958(19) 0.2042(5) 0.3893(2) 0.0698(14) Uani 1 1 d . . . H21A H 0.2200 0.2622 0.4203 0.084 Uiso 1 1 calc R . . H21B H 0.2259 0.2399 0.3671 0.084 Uiso 1 1 calc R . . C22 C 0.2338(2) 0.0660(5) 0.4092(3) 0.0891(19) Uani 1 1 d . . . H22A H 0.2276 0.0105 0.3783 0.107 Uiso 1 1 calc R . . H22B H 0.2737 0.0731 0.4318 0.107 Uiso 1 1 calc R . . C23 C 0.2073(3) 0.0020(6) 0.4412(3) 0.099(2) Uani 1 1 d . . . H23A H 0.2167 0.0525 0.4740 0.119 Uiso 1 1 calc R . . H23B H 0.2218 -0.0872 0.4515 0.119 Uiso 1 1 calc R . . C24 C 0.1441(3) -0.0039(5) 0.4080(3) 0.0903(18) Uani 1 1 d . . . H24A H 0.1344 -0.0607 0.3767 0.108 Uiso 1 1 calc R . . H24B H 0.1277 -0.0412 0.4298 0.108 Uiso 1 1 calc R . . C25 C 0.1215(2) 0.1353(5) 0.3895(2) 0.0724(14) Uani 1 1 d . . . H25A H 0.1287 0.1888 0.4212 0.087 Uiso 1 1 calc R . . H25B H 0.0814 0.1301 0.3678 0.087 Uiso 1 1 calc R . . C26 C 0.06677(19) 0.3488(5) 0.29038(19) 0.0602(12) Uani 1 1 d . . . C27 C 0.0080(2) 0.3666(6) 0.1935(2) 0.0863(17) Uani 1 1 d . . . H27A H 0.0099 0.4218 0.1657 0.104 Uiso 1 1 calc R . . H27B H -0.0172 0.4091 0.2050 0.104 Uiso 1 1 calc R . . C28 C -0.0149(2) 0.2335(7) 0.1699(3) 0.116(2) Uani 1 1 d . . . H28A H 0.0079 0.1948 0.1551 0.174 Uiso 1 1 calc R . . H28B H -0.0523 0.2435 0.1418 0.174 Uiso 1 1 calc R . . H28C H -0.0149 0.1768 0.1978 0.174 Uiso 1 1 calc R . . C29 C 0.1080(2) 0.3182(6) 0.22863(19) 0.0668(13) Uani 1 1 d . . . C30 C 0.1172(3) 0.4070(7) 0.1906(2) 0.0973(19) Uani 1 1 d . . . H30A H 0.1561 0.4278 0.2052 0.146 Uiso 1 1 calc R . . H30B H 0.0963 0.4874 0.1857 0.146 Uiso 1 1 calc R . . H30C H 0.1051 0.3632 0.1563 0.146 Uiso 1 1 calc R . . C31 C 0.1379(2) 0.2097(6) 0.2504(2) 0.0721(14) Uani 1 1 d . . . C32 C 0.1864(2) 0.1651(7) 0.2410(3) 0.098(2) Uani 1 1 d . . . H32A H 0.1903 0.0704 0.2451 0.147 Uiso 1 1 calc R . . H32B H 0.2199 0.2070 0.2670 0.147 Uiso 1 1 calc R . . H32C H 0.1798 0.1894 0.2051 0.147 Uiso 1 1 calc R . . C41 C 0.32025(19) 0.6102(5) 0.13043(19) 0.0615(12) Uani 1 1 d . . . C42 C 0.34782(18) 0.5991(4) 0.09516(18) 0.0558(11) Uani 1 1 d . . . C43 C 0.3455(2) 0.4952(5) 0.0614(2) 0.0689(13) Uani 1 1 d . . . H43 H 0.3209 0.4252 0.0552 0.083 Uiso 1 1 calc R . . C44 C 0.3804(2) 0.4972(5) 0.0370(2) 0.0731(14) Uani 1 1 d . . . H44 H 0.3785 0.4296 0.0134 0.088 Uiso 1 1 calc R . . C45 C 0.4183(2) 0.6005(5) 0.0479(2) 0.0724(14) Uani 1 1 d . . . H45 H 0.4424 0.6001 0.0321 0.087 Uiso 1 1 calc R . . C46 C 0.4207(2) 0.7044(5) 0.08196(19) 0.0665(13) Uani 1 1 d . . . H46 H 0.4466 0.7724 0.0896 0.080 Uiso 1 1 calc R . . C47 C 0.3841(2) 0.7050(5) 0.10435(18) 0.0601(12) Uani 1 1 d . . . C48 C 0.37717(19) 0.8010(5) 0.14302(18) 0.0606(12) Uani 1 1 d . . . C49 C 0.3451(2) 0.5080(5) 0.1764(2) 0.0689(13) Uani 1 1 d . . . H49A H 0.3438 0.4214 0.1606 0.083 Uiso 1 1 calc R . . H49B H 0.3840 0.5299 0.1987 0.083 Uiso 1 1 calc R . . C50 C 0.3171(2) 0.4983(5) 0.2125(2) 0.0715(14) Uani 1 1 d . . . C51 C 0.3426(2) 0.4093(5) 0.2614(2) 0.0673(13) Uani 1 1 d . . . C52 C 0.3172(2) 0.3978(6) 0.2946(2) 0.0775(15) Uani 1 1 d . . . H52 H 0.2854 0.4475 0.2869 0.093 Uiso 1 1 calc R . . C53 C 0.3379(2) 0.3143(6) 0.3389(2) 0.0850(16) Uani 1 1 d . . . H53 H 0.3202 0.3066 0.3610 0.102 Uiso 1 1 calc R . . C54 C 0.3855(3) 0.2425(6) 0.3497(2) 0.0808(15) Uani 1 1 d . . . C55 C 0.4128(2) 0.2546(5) 0.3186(2) 0.0750(14) Uani 1 1 d . . . H55 H 0.4454 0.2072 0.3272 0.090 Uiso 1 1 calc R . . C56 C 0.3914(2) 0.3375(5) 0.2745(2) 0.0705(13) Uani 1 1 d . . . H56 H 0.4097 0.3460 0.2530 0.085 Uiso 1 1 calc R . . C57 C 0.2560(2) 0.6019(6) 0.0999(2) 0.0744(14) Uani 1 1 d . . . C58 C 0.1815(3) 0.4487(8) 0.0674(3) 0.124(3) Uani 1 1 d . . . H58A H 0.1660 0.5003 0.0869 0.148 Uiso 1 1 calc R . . H58B H 0.1631 0.4758 0.0297 0.148 Uiso 1 1 calc R . . C59 C 0.1718(4) 0.3158(11) 0.0712(6) 0.205(5) Uani 1 1 d . . . H59A H 0.1851 0.2652 0.0500 0.307 Uiso 1 1 calc R . . H59B H 0.1325 0.3012 0.0579 0.307 Uiso 1 1 calc R . . H59C H 0.1910 0.2884 0.1084 0.307 Uiso 1 1 calc R . . C60 C 0.3592(2) 0.9463(5) 0.12009(19) 0.0708(14) Uani 1 1 d . . . C61 C 0.2971(3) 0.9483(6) 0.0790(3) 0.107(2) Uani 1 1 d . . . H61A H 0.2747 0.9305 0.0975 0.129 Uiso 1 1 calc R . . H61B H 0.2898 0.8791 0.0522 0.129 Uiso 1 1 calc R . . C62 C 0.2801(3) 1.0870(7) 0.0496(4) 0.147(4) Uani 1 1 d . . . H62A H 0.2430 1.0800 0.0198 0.177 Uiso 1 1 calc R . . H62B H 0.2788 1.1518 0.0749 0.177 Uiso 1 1 calc R . . C63 C 0.3200(5) 1.1375(8) 0.0277(3) 0.153(4) Uani 1 1 d . . . H63A H 0.3179 1.0794 -0.0012 0.184 Uiso 1 1 calc R . . H63B H 0.3088 1.2258 0.0127 0.184 Uiso 1 1 calc R . . C64 C 0.3756(4) 1.1412(6) 0.0695(3) 0.116(2) Uani 1 1 d . . . H64A H 0.3781 1.2024 0.0975 0.139 Uiso 1 1 calc R . . H64B H 0.4001 1.1729 0.0549 0.139 Uiso 1 1 calc R . . C65 C 0.3945(3) 1.0012(5) 0.0943(2) 0.0897(18) Uani 1 1 d . . . H65A H 0.3924 0.9408 0.0661 0.108 Uiso 1 1 calc R . . H65B H 0.4331 1.0054 0.1215 0.108 Uiso 1 1 calc R . . C66 C 0.4322(2) 0.8088(5) 0.19600(19) 0.0647(12) Uani 1 1 d . . . C67 C 0.4838(2) 0.8060(8) 0.2936(2) 0.099(2) Uani 1 1 d . . . H67A H 0.4781 0.7614 0.3218 0.119 Uiso 1 1 calc R . . H67B H 0.5100 0.7540 0.2864 0.119 Uiso 1 1 calc R . . C68 C 0.5066(3) 0.9381(8) 0.3122(3) 0.139(3) Uani 1 1 d . . . H68A H 0.5075 0.9865 0.2827 0.209 Uiso 1 1 calc R . . H68B H 0.5438 0.9303 0.3410 0.209 Uiso 1 1 calc R . . H68C H 0.4837 0.9843 0.3250 0.209 Uiso 1 1 calc R . . C69 C 0.3829(2) 0.8630(7) 0.2493(2) 0.0801(16) Uani 1 1 d . . . C70 C 0.3698(3) 0.7877(7) 0.2885(2) 0.105(2) Uani 1 1 d . . . H70A H 0.3742 0.8448 0.3179 0.158 Uiso 1 1 calc R . . H70B H 0.3947 0.7135 0.3023 0.158 Uiso 1 1 calc R . . H70C H 0.3320 0.7563 0.2705 0.158 Uiso 1 1 calc R . . C71 C 0.3543(2) 0.9693(6) 0.2211(2) 0.0828(17) Uani 1 1 d . . . C72 C 0.3017(3) 1.0185(8) 0.2225(3) 0.127(3) Uani 1 1 d . . . H72A H 0.2702 1.0021 0.1881 0.191 Uiso 1 1 calc R . . H72B H 0.3048 1.1120 0.2299 0.191 Uiso 1 1 calc R . . H72C H 0.2967 0.9724 0.2504 0.191 Uiso 1 1 calc R . . O1W O 0.5216(9) 0.472(2) 0.5024(11) 0.279(11) Uiso 0.50 1 d P . . H1A H 0.5378 0.5170 0.4827 0.419 Uiso 0.50 1 d PR . . H1B H 0.5362 0.3888 0.5033 0.419 Uiso 0.50 1 d PR . . O2W O 0.4619(8) 0.5607(18) 0.4223(8) 0.242(8) Uiso 0.50 1 d P . . H2A H 0.4692 0.6437 0.4295 0.363 Uiso 0.50 1 d PR . . H2B H 0.4555 0.5230 0.4452 0.363 Uiso 0.50 1 d PR . . O1 O 0.0000 0.5000 0.0000 0.422(13) Uiso 1 2 d SD . . H1C H -0.0272 0.4733 0.0114 0.633 Uiso 0.50 1 d PR . . C81 C 0.0076(12) 0.673(2) 0.0624(9) 0.292(16) Uiso 0.50 1 d PD . . H81A H -0.0279 0.6406 0.0576 0.438 Uiso 0.50 1 calc PR . . H81B H 0.0080 0.7686 0.0649 0.438 Uiso 0.50 1 calc PR . . H81C H 0.0366 0.6373 0.0951 0.438 Uiso 0.50 1 calc PR . . C82 C 0.0173(19) 0.6317(16) 0.0138(14) 0.41(3) Uiso 0.50 1 d PD . . H82A H -0.0036 0.6894 -0.0168 0.488 Uiso 0.50 1 calc PR . . H82B H 0.0565 0.6397 0.0231 0.488 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1135(6) 0.1707(8) 0.0815(5) 0.0539(5) 0.0526(4) 0.0311(5) Br2 0.1341(7) 0.1620(8) 0.1318(7) 0.0710(6) 0.0786(6) 0.0370(6) S1 0.0674(8) 0.0723(8) 0.0739(8) -0.0219(7) 0.0249(7) -0.0038(7) S2 0.0809(9) 0.0824(9) 0.0817(10) -0.0274(8) 0.0281(8) -0.0057(8) N11 0.051(2) 0.088(3) 0.053(2) -0.008(2) 0.0181(19) 0.004(2) N41 0.053(2) 0.115(3) 0.053(2) -0.011(2) 0.019(2) -0.001(2) O11 0.0474(16) 0.0651(18) 0.0534(17) -0.0087(14) 0.0262(14) -0.0032(14) O12 0.072(2) 0.122(3) 0.082(2) 0.025(2) 0.047(2) 0.032(2) O13 0.065(2) 0.080(2) 0.081(2) -0.018(2) 0.0279(19) -0.0209(18) O14 0.0531(19) 0.084(2) 0.076(2) 0.0031(19) 0.0255(18) 0.0049(18) O15 0.049(2) 0.116(3) 0.074(2) -0.013(2) 0.0292(18) -0.0039(19) O41 0.0463(17) 0.080(2) 0.067(2) -0.0083(17) 0.0230(16) 0.0037(16) O42 0.074(2) 0.137(3) 0.088(3) 0.024(2) 0.045(2) 0.044(2) O43 0.063(2) 0.096(3) 0.098(3) -0.003(2) 0.025(2) -0.016(2) O44 0.051(2) 0.105(3) 0.112(3) 0.017(3) 0.016(2) 0.014(2) O45 0.051(2) 0.122(3) 0.071(2) -0.010(2) 0.0266(18) 0.001(2) C1 0.054(3) 0.056(3) 0.052(2) -0.005(2) 0.026(2) -0.001(2) C2 0.052(2) 0.062(3) 0.048(2) 0.000(2) 0.023(2) 0.004(2) C3 0.072(3) 0.061(3) 0.054(3) -0.005(2) 0.026(2) 0.006(2) C4 0.092(4) 0.080(4) 0.059(3) -0.006(3) 0.042(3) 0.013(3) C5 0.088(4) 0.094(4) 0.063(3) 0.003(3) 0.052(3) 0.006(3) C6 0.065(3) 0.080(3) 0.061(3) 0.001(3) 0.039(3) -0.005(3) C7 0.052(3) 0.062(3) 0.051(2) -0.001(2) 0.023(2) 0.004(2) C8 0.047(2) 0.059(3) 0.056(2) -0.003(2) 0.025(2) 0.000(2) C9 0.057(3) 0.064(3) 0.056(3) 0.004(2) 0.031(2) 0.002(2) C10 0.058(3) 0.077(3) 0.057(3) 0.001(2) 0.030(2) 0.004(3) C11 0.055(3) 0.071(3) 0.053(3) -0.006(2) 0.031(2) -0.006(2) C12 0.055(3) 0.083(3) 0.054(3) -0.003(2) 0.033(2) -0.004(3) C13 0.054(3) 0.093(4) 0.058(3) 0.009(3) 0.029(2) 0.004(3) C14 0.067(3) 0.095(4) 0.052(3) 0.014(3) 0.028(3) 0.005(3) C15 0.075(4) 0.105(4) 0.062(3) 0.010(3) 0.044(3) 0.001(3) C16 0.058(3) 0.093(4) 0.068(3) 0.002(3) 0.037(3) 0.001(3) C17 0.057(3) 0.079(3) 0.053(3) -0.005(3) 0.029(2) -0.011(3) C18 0.073(4) 0.110(4) 0.094(4) -0.028(4) 0.029(3) -0.034(3) C19 0.086(4) 0.159(7) 0.135(6) 0.010(5) 0.065(4) -0.029(4) C20 0.052(3) 0.056(3) 0.061(3) -0.012(2) 0.018(2) -0.004(2) C21 0.059(3) 0.062(3) 0.074(3) -0.005(3) 0.017(3) -0.002(2) C22 0.067(3) 0.070(3) 0.097(4) -0.002(3) 0.008(3) 0.005(3) C23 0.111(5) 0.062(3) 0.105(5) 0.011(3) 0.031(4) 0.003(3) C24 0.096(4) 0.067(3) 0.098(4) 0.003(3) 0.036(4) -0.010(3) C25 0.073(3) 0.062(3) 0.075(3) -0.003(3) 0.027(3) -0.009(3) C26 0.049(3) 0.071(3) 0.061(3) -0.010(2) 0.025(2) -0.001(2) C27 0.062(3) 0.117(5) 0.062(3) -0.001(3) 0.013(3) 0.016(3) C28 0.067(4) 0.138(6) 0.104(5) -0.039(5) 0.005(4) -0.010(4) C29 0.058(3) 0.088(4) 0.058(3) -0.019(3) 0.028(2) -0.009(3) C30 0.091(4) 0.132(5) 0.077(4) -0.016(4) 0.045(3) -0.015(4) C31 0.052(3) 0.098(4) 0.069(3) -0.028(3) 0.030(3) -0.006(3) C32 0.072(4) 0.127(5) 0.104(4) -0.040(4) 0.048(3) -0.004(4) C41 0.053(3) 0.066(3) 0.058(3) -0.006(2) 0.019(2) 0.000(2) C42 0.052(3) 0.057(3) 0.050(2) 0.003(2) 0.016(2) 0.005(2) C43 0.063(3) 0.068(3) 0.069(3) -0.004(3) 0.024(3) 0.004(2) C44 0.081(4) 0.073(3) 0.063(3) 0.000(3) 0.031(3) 0.014(3) C45 0.084(4) 0.079(3) 0.060(3) 0.007(3) 0.038(3) 0.016(3) C46 0.062(3) 0.075(3) 0.064(3) 0.007(3) 0.030(3) 0.005(3) C47 0.057(3) 0.067(3) 0.048(2) 0.001(2) 0.017(2) 0.011(2) C48 0.051(3) 0.067(3) 0.056(3) -0.001(2) 0.018(2) 0.007(2) C49 0.058(3) 0.081(3) 0.069(3) 0.002(3) 0.029(3) 0.007(3) C50 0.067(3) 0.080(3) 0.066(3) -0.002(3) 0.029(3) 0.004(3) C51 0.053(3) 0.083(3) 0.073(3) -0.003(3) 0.034(3) -0.002(3) C52 0.065(3) 0.089(4) 0.091(4) -0.003(3) 0.046(3) 0.008(3) C53 0.081(4) 0.104(4) 0.089(4) 0.015(4) 0.054(3) 0.006(3) C54 0.081(4) 0.090(4) 0.079(4) 0.016(3) 0.042(3) 0.005(3) C55 0.062(3) 0.086(4) 0.083(4) 0.018(3) 0.039(3) 0.014(3) C56 0.064(3) 0.085(3) 0.079(3) 0.004(3) 0.047(3) 0.011(3) C57 0.053(3) 0.089(4) 0.074(3) 0.004(3) 0.022(3) 0.001(3) C58 0.073(4) 0.138(6) 0.140(7) 0.003(5) 0.031(4) -0.032(4) C59 0.116(7) 0.169(9) 0.344(17) 0.016(10) 0.116(9) -0.035(7) C60 0.072(3) 0.063(3) 0.055(3) -0.015(2) 0.009(3) 0.003(3) C61 0.089(4) 0.071(4) 0.104(5) -0.024(3) -0.007(4) 0.017(3) C62 0.118(6) 0.070(4) 0.137(7) -0.023(4) -0.046(5) 0.035(4) C63 0.226(12) 0.078(5) 0.090(5) 0.004(4) 0.014(7) -0.004(6) C64 0.164(7) 0.067(4) 0.092(5) 0.000(4) 0.037(5) 0.005(4) C65 0.133(5) 0.061(3) 0.075(4) -0.002(3) 0.047(4) -0.001(3) C66 0.053(3) 0.079(3) 0.057(3) -0.008(2) 0.020(2) 0.002(2) C67 0.076(4) 0.152(6) 0.060(3) -0.006(4) 0.023(3) -0.003(4) C68 0.100(5) 0.142(7) 0.129(7) -0.040(6) 0.010(5) -0.006(5) C69 0.068(3) 0.112(5) 0.060(3) -0.021(3) 0.028(3) -0.009(3) C70 0.098(5) 0.148(6) 0.084(4) -0.018(4) 0.053(4) -0.017(4) C71 0.060(3) 0.106(4) 0.083(4) -0.044(4) 0.033(3) -0.017(3) C72 0.075(4) 0.144(6) 0.164(7) -0.067(6) 0.055(5) -0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C14 1.899(5) . ? Br2 C54 1.892(5) . ? S1 C31 1.770(6) . ? S1 C20 1.844(4) . ? S2 C71 1.747(7) . ? S2 C60 1.852(5) . ? N11 C26 1.357(6) . ? N11 C29 1.411(6) . ? N11 C27 1.488(6) . ? N41 C66 1.352(6) . ? N41 C69 1.430(7) . ? N41 C67 1.480(7) . ? O11 C1 1.430(5) . ? O11 C8 1.444(5) . ? O12 C10 1.221(6) . ? O13 C17 1.347(6) . ? O13 C18 1.446(6) . ? O14 C17 1.177(6) . ? O15 C26 1.224(5) . ? O41 C48 1.427(6) . ? O41 C41 1.445(5) . ? O42 C50 1.212(6) . ? O43 C57 1.330(7) . ? O43 C58 1.470(7) . ? O44 C57 1.185(6) . ? O45 C66 1.221(6) . ? C1 C2 1.505(6) . ? C1 C9 1.531(6) . ? C1 C17 1.535(7) . ? C2 C7 1.382(6) . ? C2 C3 1.391(6) . ? C3 C4 1.362(7) . ? C3 H3 0.9300 . ? C4 C5 1.375(8) . ? C4 H4 0.9300 . ? C5 C6 1.376(7) . ? C5 H5 0.9300 . ? C6 C7 1.385(6) . ? C6 H6 0.9300 . ? C7 C8 1.519(6) . ? C8 C26 1.553(6) . ? C8 C20 1.581(6) . ? C9 C10 1.505(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.483(7) . ? C11 C12 1.372(6) . ? C11 C16 1.395(6) . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.361(7) . ? C13 H13 0.9300 . ? C14 C15 1.388(7) . ? C15 C16 1.380(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 C19 1.457(9) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.519(6) . ? C20 C25 1.527(7) . ? C21 C22 1.530(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.510(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.524(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.522(7) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.496(8) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.330(7) . ? C29 C30 1.485(8) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 C32 1.509(7) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C41 C42 1.473(7) . ? C41 C49 1.535(7) . ? C41 C57 1.546(7) . ? C42 C43 1.385(7) . ? C42 C47 1.390(6) . ? C43 C44 1.381(7) . ? C43 H43 0.9300 . ? C44 C45 1.391(7) . ? C44 H44 0.9300 . ? C45 C46 1.391(7) . ? C45 H45 0.9300 . ? C46 C47 1.382(7) . ? C46 H46 0.9300 . ? C47 C48 1.514(6) . ? C48 C66 1.544(6) . ? C48 C60 1.581(7) . ? C49 C50 1.500(7) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 C51 1.506(7) . ? C51 C52 1.375(7) . ? C51 C56 1.396(7) . ? C52 C53 1.381(8) . ? C52 H52 0.9300 . ? C53 C54 1.382(8) . ? C53 H53 0.9300 . ? C54 C55 1.367(7) . ? C55 C56 1.372(7) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C58 C59 1.376(11) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 C65 1.527(8) . ? C60 C61 1.539(8) . ? C61 C62 1.575(9) . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C62 C63 1.538(13) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C63 C64 1.419(11) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C64 C65 1.550(8) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C67 C68 1.458(10) . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? C69 C71 1.344(8) . ? C69 C70 1.490(8) . ? C70 H70A 0.9600 . ? C70 H70B 0.9600 . ? C70 H70C 0.9600 . ? C71 C72 1.516(8) . ? C72 H72A 0.9600 . ? C72 H72B 0.9600 . ? C72 H72C 0.9600 . ? O1W H1A 0.9542 . ? O1W H1B 0.9173 . ? O2W H2A 0.8614 . ? O2W H2B 0.8220 . ? O1 C82 1.4002(11) 3_565 ? O1 C82 1.4002(11) . ? O1 H1C 0.9573 . ? C81 C82 1.5399(10) . ? C81 H81A 0.9600 . ? C81 H81B 0.9600 . ? C81 H81C 0.9600 . ? C82 H82A 0.9700 . ? C82 H82B 0.9700 . ? 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 C31 S1 C20 103.6(2) . . ? C71 S2 C60 105.5(3) . . ? C26 N11 C29 123.7(4) . . ? C26 N11 C27 117.0(4) . . ? C29 N11 C27 116.2(4) . . ? C66 N41 C69 123.3(4) . . ? C66 N41 C67 117.0(4) . . ? C69 N41 C67 117.6(4) . . ? C1 O11 C8 112.1(3) . . ? C17 O13 C18 116.6(4) . . ? C48 O41 C41 112.1(3) . . ? C57 O43 C58 115.0(5) . . ? O11 C1 C2 104.4(3) . . ? O11 C1 C9 108.6(3) . . ? C2 C1 C9 111.2(4) . . ? O11 C1 C17 109.3(4) . . ? C2 C1 C17 110.2(4) . . ? C9 C1 C17 112.8(4) . . ? C7 C2 C3 121.1(4) . . ? C7 C2 C1 109.4(4) . . ? C3 C2 C1 129.5(4) . . ? C4 C3 C2 118.8(5) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 121.9(5) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C7 118.3(5) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C2 C7 C6 119.6(4) . . ? C2 C7 C8 109.2(4) . . ? C6 C7 C8 131.2(4) . . ? O11 C8 C7 103.8(3) . . ? O11 C8 C26 110.4(4) . . ? C7 C8 C26 109.7(4) . . ? O11 C8 C20 108.5(3) . . ? C7 C8 C20 115.2(4) . . ? C26 C8 C20 109.1(3) . . ? C10 C9 C1 113.7(4) . . ? C10 C9 H9A 108.8 . . ? C1 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C1 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O12 C10 C11 121.0(4) . . ? O12 C10 C9 119.2(4) . . ? C11 C10 C9 119.7(4) . . ? C12 C11 C16 118.9(4) . . ? C12 C11 C10 122.9(4) . . ? C16 C11 C10 118.2(4) . . ? C11 C12 C13 121.3(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 118.9(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 121.9(5) . . ? C13 C14 Br1 118.7(4) . . ? C15 C14 Br1 119.4(4) . . ? C16 C15 C14 118.4(5) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C11 120.6(5) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? O14 C17 O13 125.3(4) . . ? O14 C17 C1 126.8(5) . . ? O13 C17 C1 107.7(4) . . ? O13 C18 C19 109.7(5) . . ? O13 C18 H18A 109.7 . . ? C19 C18 H18A 109.7 . . ? O13 C18 H18B 109.7 . . ? C19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 108.6(4) . . ? C21 C20 C8 110.0(4) . . ? C25 C20 C8 112.6(4) . . ? C21 C20 S1 112.3(3) . . ? C25 C20 S1 104.9(3) . . ? C8 C20 S1 108.4(3) . . ? C20 C21 C22 113.4(4) . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 111.2(5) . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C24 110.9(5) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C23 109.5(5) . . ? C25 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? C25 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? C24 C25 C20 113.7(5) . . ? C24 C25 H25A 108.8 . . ? C20 C25 H25A 108.8 . . ? C24 C25 H25B 108.8 . . ? C20 C25 H25B 108.8 . . ? H25A C25 H25B 107.7 . . ? O15 C26 N11 122.5(4) . . ? O15 C26 C8 118.7(4) . . ? N11 C26 C8 118.6(4) . . ? N11 C27 C28 112.5(5) . . ? N11 C27 H27A 109.1 . . ? C28 C27 H27A 109.1 . . ? N11 C27 H27B 109.1 . . ? C28 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 N11 121.6(5) . . ? C31 C29 C30 123.7(5) . . ? N11 C29 C30 114.6(5) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 C32 124.1(6) . . ? C29 C31 S1 120.8(4) . . ? C32 C31 S1 115.1(5) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O41 C41 C42 104.0(4) . . ? O41 C41 C49 109.5(4) . . ? C42 C41 C49 109.7(4) . . ? O41 C41 C57 107.0(4) . . ? C42 C41 C57 114.1(4) . . ? C49 C41 C57 112.1(4) . . ? C43 C42 C47 121.1(5) . . ? C43 C42 C41 128.5(5) . . ? C47 C42 C41 110.0(4) . . ? C44 C43 C42 119.0(5) . . ? C44 C43 H43 120.5 . . ? C42 C43 H43 120.5 . . ? C43 C44 C45 119.9(5) . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C46 C45 C44 120.9(5) . . ? C46 C45 H45 119.5 . . ? C44 C45 H45 119.5 . . ? C47 C46 C45 118.9(5) . . ? C47 C46 H46 120.5 . . ? C45 C46 H46 120.5 . . ? C46 C47 C42 119.9(4) . . ? C46 C47 C48 131.3(5) . . ? C42 C47 C48 108.7(4) . . ? O41 C48 C47 103.7(4) . . ? O41 C48 C66 110.8(4) . . ? C47 C48 C66 109.4(4) . . ? O41 C48 C60 109.2(4) . . ? C47 C48 C60 114.8(4) . . ? C66 C48 C60 108.8(4) . . ? C50 C49 C41 115.7(4) . . ? C50 C49 H49A 108.4 . . ? C41 C49 H49A 108.4 . . ? C50 C49 H49B 108.4 . . ? C41 C49 H49B 108.4 . . ? H49A C49 H49B 107.4 . . ? O42 C50 C49 120.9(5) . . ? O42 C50 C51 120.7(5) . . ? C49 C50 C51 118.3(4) . . ? C52 C51 C56 118.5(5) . . ? C52 C51 C50 119.2(5) . . ? C56 C51 C50 122.3(5) . . ? C51 C52 C53 121.5(5) . . ? C51 C52 H52 119.3 . . ? C53 C52 H52 119.3 . . ? C52 C53 C54 118.1(5) . . ? C52 C53 H53 120.9 . . ? C54 C53 H53 120.9 . . ? C55 C54 C53 121.9(5) . . ? C55 C54 Br2 119.4(4) . . ? C53 C54 Br2 118.7(4) . . ? C54 C55 C56 119.1(5) . . ? C54 C55 H55 120.5 . . ? C56 C55 H55 120.5 . . ? C55 C56 C51 120.9(5) . . ? C55 C56 H56 119.6 . . ? C51 C56 H56 119.6 . . ? O44 C57 O43 124.9(5) . . ? O44 C57 C41 126.7(5) . . ? O43 C57 C41 108.4(5) . . ? C59 C58 O43 110.6(7) . . ? C59 C58 H58A 109.5 . . ? O43 C58 H58A 109.5 . . ? C59 C58 H58B 109.5 . . ? O43 C58 H58B 109.5 . . ? H58A C58 H58B 108.1 . . ? C58 C59 H59A 109.5 . . ? C58 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C58 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C65 C60 C61 110.3(5) . . ? C65 C60 C48 112.4(4) . . ? C61 C60 C48 110.0(4) . . ? C65 C60 S2 104.7(3) . . ? C61 C60 S2 111.2(4) . . ? C48 C60 S2 108.2(3) . . ? C60 C61 C62 111.0(5) . . ? C60 C61 H61A 109.4 . . ? C62 C61 H61A 109.4 . . ? C60 C61 H61B 109.4 . . ? C62 C61 H61B 109.4 . . ? H61A C61 H61B 108.0 . . ? C63 C62 C61 113.9(7) . . ? C63 C62 H62A 108.8 . . ? C61 C62 H62A 108.8 . . ? C63 C62 H62B 108.8 . . ? C61 C62 H62B 108.8 . . ? H62A C62 H62B 107.7 . . ? C64 C63 C62 110.7(7) . . ? C64 C63 H63A 109.5 . . ? C62 C63 H63A 109.5 . . ? C64 C63 H63B 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 108.1 . . ? C63 C64 C65 110.6(6) . . ? C63 C64 H64A 109.5 . . ? C65 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? C65 C64 H64B 109.5 . . ? H64A C64 H64B 108.1 . . ? C60 C65 C64 112.8(6) . . ? C60 C65 H65A 109.0 . . ? C64 C65 H65A 109.0 . . ? C60 C65 H65B 109.0 . . ? C64 C65 H65B 109.0 . . ? H65A C65 H65B 107.8 . . ? O45 C66 N41 121.9(4) . . ? O45 C66 C48 118.9(4) . . ? N41 C66 C48 119.1(4) . . ? C68 C67 N41 110.5(6) . . ? C68 C67 H67A 109.5 . . ? N41 C67 H67A 109.5 . . ? C68 C67 H67B 109.5 . . ? N41 C67 H67B 109.5 . . ? H67A C67 H67B 108.1 . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? C71 C69 N41 120.8(5) . . ? C71 C69 C70 124.5(6) . . ? N41 C69 C70 114.7(6) . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C69 C71 C72 122.8(6) . . ? C69 C71 S2 122.5(4) . . ? C72 C71 S2 114.6(6) . . ? C71 C72 H72A 109.5 . . ? C71 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C71 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? O1W O1W H1A 111.3 3_666 . ? H2A O2W H2B 112.0 . . ? C82 O1 C82 180(3) 3_565 . ? C82 O1 H1C 112.7 . . ? C82 C81 H81A 109.5 . . ? C82 C81 H81B 109.5 . . ? H81A C81 H81B 109.5 . . ? C82 C81 H81C 109.5 . . ? H81A C81 H81C 109.5 . . ? H81B C81 H81C 109.5 . . ? O1 C82 C81 109.32(11) . . ? O1 C82 H82A 109.8 . . ? C81 C82 H82A 109.8 . . ? O1 C82 H82B 109.8 . . ? C81 C82 H82B 109.8 . . ? H82A C82 H82B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 1.023 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.076