# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Chris Orvig' 'Karin Bohmerle' 'Meryn L. Bowen' 'David E. Green' 'Michael Merkel' 'Brian O. Patrick' 'Harvey J. Schugar' 'Lauren E. Scott' 'Tim Storr' 'Katherine H. Thompson' _publ_contact_author_name 'Chris Orvig' _publ_contact_author_email ORVIG@CHEM.UBC.CA _publ_section_title ; In vitro studies of 3-hydroxy-4-pyridinones and their glycosylated derivatives as potential agents for Alzheimer's disease ; # Attachment 'co264.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 746849' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 N O7' _chemical_formula_weight 301.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2508(8) _cell_length_b 8.0153(6) _cell_length_c 11.6332(12) _cell_angle_alpha 90.00 _cell_angle_beta 113.797(4) _cell_angle_gamma 90.00 _cell_volume 703.93(11) _cell_formula_units_Z 2 _cell_measurement_temperature 253(2) _cell_measurement_reflns_used 5046 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 30.5 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 253(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/ADSC CCD' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1678 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.87 _reflns_number_total 1678 _reflns_number_gt 1476 _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^)+(0.0807P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(15) _refine_ls_number_reflns 1678 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.009 _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 0.6852(2) 0.1930(2) 0.15950(16) 0.0216(4) Uani 1 1 d . . . O2 O 1.1525(2) 0.1419(3) 0.21814(18) 0.0324(5) Uani 1 1 d . . . O3 O 0.9980(2) 0.2575(3) -0.03815(17) 0.0296(5) Uani 1 1 d . . . O4 O 0.6774(3) 0.4497(3) -0.1000(2) 0.0362(6) Uani 1 1 d . . . O5 O 0.3534(3) 0.3407(4) 0.0873(2) 0.0447(7) Uani 1 1 d . . . O6 O 0.8942(2) 0.0441(2) 0.31170(16) 0.0229(4) Uani 1 1 d . . . O7 O 1.2350(3) 0.1262(5) 0.4657(2) 0.0513(8) Uani 1 1 d . . . N1 N 0.8570(3) 0.1107(4) 0.6086(2) 0.0370(7) Uani 1 1 d . . . C1 C 0.8692(3) 0.1832(3) 0.2326(2) 0.0187(5) Uani 1 1 d . . . H1 H 0.9125 0.2852 0.2819 0.022 Uiso 1 1 calc R . . C2 C 0.9667(3) 0.1513(4) 0.1478(2) 0.0208(5) Uani 1 1 d . . . H2 H 0.9255 0.0454 0.1035 0.025 Uiso 1 1 calc R . . C3 C 0.9248(3) 0.2908(4) 0.0515(2) 0.0209(5) Uani 1 1 d . . . H3 H 0.9732 0.3959 0.0947 0.025 Uiso 1 1 calc R . . C4 C 0.7258(3) 0.3081(4) -0.0208(2) 0.0215(5) Uani 1 1 d . . . H4 H 0.6796 0.2076 -0.0714 0.026 Uiso 1 1 calc R . . C5 C 0.6379(3) 0.3278(4) 0.0718(2) 0.0213(5) Uani 1 1 d . . . H5 H 0.6745 0.4337 0.1170 0.026 Uiso 1 1 calc R . . C6 C 0.4376(3) 0.3231(4) 0.0039(3) 0.0304(7) Uani 1 1 d . . . H6A H 0.3992 0.4123 -0.0576 0.036 Uiso 1 1 calc R . . H6B H 0.4023 0.2180 -0.0406 0.036 Uiso 1 1 calc R . . C7 C 0.8093(4) 0.0766(4) 0.4833(3) 0.0299(6) Uani 1 1 d . . . C8 C 0.9378(3) 0.0824(4) 0.4370(2) 0.0233(5) Uani 1 1 d . . . C9 C 1.1209(4) 0.1204(5) 0.5116(3) 0.0324(7) Uani 1 1 d . . . C10 C 1.1576(4) 0.1528(5) 0.6403(3) 0.0396(8) Uani 1 1 d . . . H10 H 1.2729 0.1768 0.6960 0.047 Uiso 1 1 calc R . . C11 C 1.0273(4) 0.1490(5) 0.6827(3) 0.0374(7) Uani 1 1 d . . . H11 H 1.0559 0.1738 0.7668 0.045 Uiso 1 1 calc R . . C12 C 0.6216(4) 0.0323(7) 0.4044(3) 0.0503(11) Uani 1 1 d . . . H12A H 0.6071 0.0167 0.3190 0.075 Uiso 1 1 calc R . . H12B H 0.5454 0.1207 0.4082 0.075 Uiso 1 1 calc R . . H12C H 0.5914 -0.0689 0.4352 0.075 Uiso 1 1 calc R . . C13 C 0.7251(5) 0.1031(9) 0.6641(3) 0.0708(17) Uani 1 1 d . . . H13A H 0.7801 0.1337 0.7512 0.106 Uiso 1 1 calc R . . H13B H 0.6792 -0.0083 0.6567 0.106 Uiso 1 1 calc R . . H13C H 0.6299 0.1790 0.6205 0.106 Uiso 1 1 calc R . . H17 H 0.400(7) 0.245(9) 0.150(5) 0.092(18) Uiso 1 1 d . . . H16 H 0.760(5) 0.477(6) -0.133(3) 0.045(10) Uiso 1 1 d . . . H15 H 1.106(5) 0.279(6) -0.006(3) 0.040(10) Uiso 1 1 d . . . H14 H 1.182(6) 0.119(8) 0.296(5) 0.071(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0157(7) 0.0260(10) 0.0239(8) 0.0054(8) 0.0089(6) 0.0009(7) O2 0.0172(8) 0.0549(15) 0.0263(9) 0.0069(11) 0.0101(7) 0.0115(9) O3 0.0216(8) 0.0485(13) 0.0245(10) 0.0045(9) 0.0152(8) 0.0061(9) O4 0.0247(9) 0.0467(15) 0.0424(12) 0.0257(11) 0.0192(9) 0.0115(9) O5 0.0269(10) 0.0655(18) 0.0500(14) 0.0146(14) 0.0241(10) 0.0083(11) O6 0.0299(9) 0.0230(10) 0.0171(8) -0.0003(7) 0.0108(7) 0.0014(7) O7 0.0299(10) 0.092(2) 0.0300(10) -0.0006(14) 0.0101(8) -0.0092(13) N1 0.0449(13) 0.0482(18) 0.0225(11) 0.0037(12) 0.0183(10) 0.0145(13) C1 0.0174(10) 0.0209(13) 0.0190(11) 0.0004(10) 0.0085(9) 0.0015(9) C2 0.0159(9) 0.0281(14) 0.0185(10) 0.0007(10) 0.0071(8) 0.0042(9) C3 0.0152(10) 0.0281(14) 0.0209(11) 0.0002(10) 0.0088(9) 0.0021(9) C4 0.0156(10) 0.0288(15) 0.0190(11) 0.0040(11) 0.0059(9) 0.0012(10) C5 0.0161(10) 0.0226(14) 0.0270(13) 0.0051(11) 0.0105(9) 0.0018(9) C6 0.0198(11) 0.0366(17) 0.0365(15) 0.0127(14) 0.0132(11) 0.0026(11) C7 0.0322(13) 0.0364(17) 0.0211(12) 0.0041(12) 0.0106(10) 0.0097(12) C8 0.0291(12) 0.0239(14) 0.0165(11) 0.0009(10) 0.0088(9) 0.0041(10) C9 0.0309(13) 0.0400(18) 0.0231(13) 0.0030(13) 0.0074(10) -0.0019(13) C10 0.0421(15) 0.047(2) 0.0216(12) 0.0015(15) 0.0044(11) -0.0093(15) C11 0.0551(18) 0.0374(18) 0.0185(12) -0.0006(13) 0.0134(12) 0.0048(15) C12 0.0300(14) 0.092(3) 0.0331(15) 0.001(2) 0.0166(13) 0.0011(17) C13 0.053(2) 0.134(5) 0.0359(17) 0.002(3) 0.0294(16) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.412(3) . ? O1 C5 1.428(3) . ? O2 C2 1.419(3) . ? O2 H14 0.86(5) . ? O3 C3 1.426(3) . ? O3 H15 0.84(4) . ? O4 C4 1.414(3) . ? O4 H16 0.93(4) . ? O5 C6 1.410(4) . ? O5 H17 1.02(7) . ? O6 C8 1.388(3) . ? O6 C1 1.407(3) . ? O7 C9 1.256(4) . ? N1 C11 1.354(4) . ? N1 C7 1.376(4) . ? N1 C13 1.474(4) . ? C1 C2 1.525(3) . ? C1 H1 0.9800 . ? C2 C3 1.520(4) . ? C2 H2 0.9800 . ? C3 C4 1.520(3) . ? C3 H3 0.9800 . ? C4 C5 1.530(3) . ? C4 H4 0.9800 . ? C5 C6 1.518(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.370(4) . ? C7 C12 1.490(4) . ? C8 C9 1.439(4) . ? C9 C10 1.427(4) . ? C10 C11 1.352(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C1 O1 C5 112.92(17) . . ? C2 O2 H14 113(3) . . ? C3 O3 H15 109(3) . . ? C4 O4 H16 113(3) . . ? C6 O5 H17 105(3) . . ? C8 O6 C1 114.8(2) . . ? C11 N1 C7 120.0(2) . . ? C11 N1 C13 119.4(3) . . ? C7 N1 C13 120.7(3) . . ? O6 C1 O1 106.02(18) . . ? O6 C1 C2 108.3(2) . . ? O1 C1 C2 109.88(18) . . ? O6 C1 H1 110.8 . . ? O1 C1 H1 110.8 . . ? C2 C1 H1 110.8 . . ? O2 C2 C3 109.6(2) . . ? O2 C2 C1 111.39(19) . . ? C3 C2 C1 109.3(2) . . ? O2 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? O3 C3 C4 107.14(19) . . ? O3 C3 C2 111.3(2) . . ? C4 C3 C2 110.4(2) . . ? O3 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? O4 C4 C3 113.1(2) . . ? O4 C4 C5 106.7(2) . . ? C3 C4 C5 109.47(18) . . ? O4 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? O1 C5 C6 106.2(2) . . ? O1 C5 C4 110.7(2) . . ? C6 C5 C4 110.9(2) . . ? O1 C5 H5 109.6 . . ? C6 C5 H5 109.6 . . ? C4 C5 H5 109.6 . . ? O5 C6 C5 112.0(2) . . ? O5 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? O5 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 N1 118.3(2) . . ? C8 C7 C12 122.9(2) . . ? N1 C7 C12 118.8(2) . . ? C7 C8 O6 119.4(2) . . ? C7 C8 C9 124.1(2) . . ? O6 C8 C9 116.4(2) . . ? O7 C9 C10 124.2(3) . . ? O7 C9 C8 122.4(2) . . ? C10 C9 C8 113.4(3) . . ? C11 C10 C9 121.1(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 N1 123.1(2) . . ? C10 C11 H11 118.4 . . ? N1 C11 H11 118.4 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O6 C1 O1 -107.6(2) . . . . ? C8 O6 C1 C2 134.5(2) . . . . ? C5 O1 C1 O6 -179.03(19) . . . . ? C5 O1 C1 C2 -62.2(3) . . . . ? O6 C1 C2 O2 -65.0(3) . . . . ? O1 C1 C2 O2 179.6(2) . . . . ? O6 C1 C2 C3 173.67(19) . . . . ? O1 C1 C2 C3 58.3(3) . . . . ? O2 C2 C3 O3 63.7(3) . . . . ? C1 C2 C3 O3 -173.9(2) . . . . ? O2 C2 C3 C4 -177.4(2) . . . . ? C1 C2 C3 C4 -55.0(3) . . . . ? O3 C3 C4 O4 -66.5(3) . . . . ? C2 C3 C4 O4 172.1(2) . . . . ? O3 C3 C4 C5 174.8(2) . . . . ? C2 C3 C4 C5 53.4(3) . . . . ? C1 O1 C5 C6 -178.7(2) . . . . ? C1 O1 C5 C4 60.8(3) . . . . ? O4 C4 C5 O1 -177.69(19) . . . . ? C3 C4 C5 O1 -55.0(3) . . . . ? O4 C4 C5 C6 64.7(3) . . . . ? C3 C4 C5 C6 -172.7(2) . . . . ? O1 C5 C6 O5 59.5(3) . . . . ? C4 C5 C6 O5 179.9(3) . . . . ? C11 N1 C7 C8 0.0(5) . . . . ? C13 N1 C7 C8 -178.8(4) . . . . ? C11 N1 C7 C12 179.1(4) . . . . ? C13 N1 C7 C12 0.2(6) . . . . ? N1 C7 C8 O6 178.3(3) . . . . ? C12 C7 C8 O6 -0.7(5) . . . . ? N1 C7 C8 C9 0.7(5) . . . . ? C12 C7 C8 C9 -178.3(4) . . . . ? C1 O6 C8 C7 100.6(3) . . . . ? C1 O6 C8 C9 -81.6(3) . . . . ? C7 C8 C9 O7 -179.3(4) . . . . ? O6 C8 C9 O7 3.0(5) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? O6 C8 C9 C10 -177.9(3) . . . . ? O7 C9 C10 C11 178.1(4) . . . . ? C8 C9 C10 C11 -1.0(5) . . . . ? C9 C10 C11 N1 1.8(6) . . . . ? C7 N1 C11 C10 -1.3(5) . . . . ? C13 N1 C11 C10 177.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.529 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.077 # Attachment 'co301.cif' data_co301 _database_code_depnum_ccdc_archive 'CCDC 746850' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Cu N2 O6 S2' _chemical_formula_weight 732.42 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' Cu Cu 0.3201 1.2651 '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 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.8807(19) _cell_length_b 21.182(2) _cell_length_c 10.6465(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.614(4) _cell_angle_gamma 90.00 _cell_volume 3741.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7462 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.06 _exptl_crystal_description needle _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1548 _exptl_absorpt_coefficient_mu 0.740 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.755 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 91728 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.83 _reflns_number_total 8793 _reflns_number_gt 5990 _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^)+(0.0494P)^2^+1.7533P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8793 _refine_ls_number_parameters 523 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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 C1 C 0.48787(14) 0.06518(13) 0.8411(2) 0.0422(6) Uani 1 1 d . A . C2 C 0.41010(13) 0.08275(11) 0.8519(2) 0.0354(5) Uani 1 1 d . . . C3 C 0.34313(14) 0.04603(12) 0.7903(2) 0.0398(6) Uani 1 1 d . . . C4 C 0.35870(16) -0.00724(15) 0.7210(3) 0.0573(8) Uani 1 1 d . . . H4 H 0.3154 -0.0333 0.6818 0.069 Uiso 1 1 calc R . . C5 C 0.43582(16) -0.02196(15) 0.7094(3) 0.0554(7) Uani 1 1 d . A . H5 H 0.4454 -0.0576 0.6601 0.067 Uiso 1 1 calc R . . C6 C 0.55986(16) 0.10050(17) 0.9110(3) 0.0677(9) Uani 1 1 d . . . H6A H 0.5993 0.0705 0.9561 0.102 Uiso 1 1 calc R . . H6B H 0.5429 0.1294 0.9728 0.102 Uiso 1 1 calc R . . H6C H 0.5844 0.1246 0.8496 0.102 Uiso 1 1 calc R . . C7 C 0.57845(15) -0.00320(14) 0.7442(2) 0.0485(7) Uani 1 1 d . A . C8 C 0.61792(18) -0.05506(17) 0.8039(3) 0.0669(9) Uani 1 1 d . . . H8 H 0.5947 -0.0792 0.8630 0.080 Uiso 1 1 calc R . . C9 C 0.6932(2) -0.07143(19) 0.7754(3) 0.0815(11) Uani 1 1 d . A . H9 H 0.7205 -0.1076 0.8148 0.098 Uiso 1 1 calc R . . C10 C 0.72884(18) -0.03611(19) 0.6910(3) 0.0714(10) Uani 1 1 d D . . C11 C 0.68682(18) 0.01532(18) 0.6330(3) 0.0697(10) Uani 1 1 d . A . H11 H 0.7101 0.0402 0.5751 0.084 Uiso 1 1 calc R . . C12 C 0.61201(16) 0.03138(16) 0.6570(3) 0.0601(8) Uani 1 1 d . . . H12 H 0.5835 0.0661 0.6139 0.072 Uiso 1 1 calc R A . C13 C 0.8123(3) -0.0490(4) 0.6501(8) 0.045(2) Uani 0.552(14) 1 d PD A 1 H13 H 0.8247 -0.0153 0.5909 0.054 Uiso 0.552(14) 1 calc PR A 1 C14 C 0.7961(9) -0.1120(8) 0.5796(18) 0.144(8) Uani 0.552(14) 1 d P A 1 H14A H 0.7510 -0.1071 0.5078 0.216 Uiso 0.552(14) 1 calc PR A 1 H14B H 0.7825 -0.1441 0.6385 0.216 Uiso 0.552(14) 1 calc PR A 1 H14C H 0.8443 -0.1251 0.5474 0.216 Uiso 0.552(14) 1 calc PR A 1 C15 C 0.8793(4) -0.0539(4) 0.7667(9) 0.054(2) Uani 0.552(14) 1 d P A 1 H15A H 0.8657 -0.0875 0.8237 0.065 Uiso 0.552(14) 1 calc PR A 1 H15B H 0.9300 -0.0661 0.7389 0.065 Uiso 0.552(14) 1 calc PR A 1 C16 C 0.8924(11) 0.0076(9) 0.841(2) 0.077(5) Uani 0.552(14) 1 d P A 1 H16A H 0.9377 0.0029 0.9121 0.115 Uiso 0.552(14) 1 calc PR A 1 H16B H 0.8435 0.0184 0.8735 0.115 Uiso 0.552(14) 1 calc PR A 1 H16C H 0.9043 0.0414 0.7839 0.115 Uiso 0.552(14) 1 calc PR A 1 C17 C 0.07527(12) 0.19256(10) 1.0246(2) 0.0284(5) Uani 1 1 d . B . C18 C 0.15197(12) 0.18182(10) 0.99985(19) 0.0274(4) Uani 1 1 d . . . C19 C 0.21842(13) 0.21949(10) 1.0617(2) 0.0316(5) Uani 1 1 d . . . C20 C 0.20355(14) 0.26553(11) 1.1488(2) 0.0378(5) Uani 1 1 d . . . H20 H 0.2466 0.2908 1.1920 0.045 Uiso 1 1 calc R . . C21 C 0.12718(14) 0.27421(11) 1.1719(2) 0.0350(5) Uani 1 1 d . B . H21 H 0.1178 0.3056 1.2313 0.042 Uiso 1 1 calc R . . C22 C 0.00448(13) 0.15511(11) 0.9593(2) 0.0356(5) Uani 1 1 d . . . H22A H -0.0166 0.1296 1.0225 0.053 Uiso 1 1 calc R . . H22B H 0.0213 0.1274 0.8953 0.053 Uiso 1 1 calc R . . H22C H -0.0376 0.1839 0.9171 0.053 Uiso 1 1 calc R . . C23 C -0.01463(13) 0.25009(10) 1.1431(2) 0.0304(5) Uani 1 1 d . B . C24 C -0.04469(13) 0.20900(10) 1.2239(2) 0.0342(5) Uani 1 1 d . . . H24 H -0.0140 0.1735 1.2588 0.041 Uiso 1 1 calc R . . C25 C -0.11980(14) 0.22016(12) 1.2534(2) 0.0420(6) Uani 1 1 d . B . H25 H -0.1402 0.1920 1.3092 0.050 Uiso 1 1 calc R . . C26 C -0.16634(16) 0.27184(14) 1.2031(3) 0.0536(7) Uani 1 1 d . . . C27 C -0.13411(16) 0.31207(13) 1.1227(3) 0.0507(7) Uani 1 1 d . B . H27 H -0.1647 0.3477 1.0877 0.061 Uiso 1 1 calc R . . C28 C -0.05909(15) 0.30216(11) 1.0917(2) 0.0381(5) Uani 1 1 d . . . H28 H -0.0384 0.3304 1.0365 0.046 Uiso 1 1 calc R B . C29 C -0.2405(3) 0.2952(3) 1.2562(7) 0.0442(15) Uani 0.581(10) 1 d P B 1 H29 H -0.2748 0.3191 1.1854 0.053 Uiso 0.581(10) 1 calc PR B 1 C30 C -0.2209(13) 0.3395(10) 1.365(2) 0.078(5) Uani 0.581(10) 1 d P B 1 H30A H -0.2708 0.3529 1.3921 0.116 Uiso 0.581(10) 1 calc PR B 1 H30B H -0.1932 0.3765 1.3388 0.116 Uiso 0.581(10) 1 calc PR B 1 H30C H -0.1858 0.3184 1.4363 0.116 Uiso 0.581(10) 1 calc PR B 1 C31 C -0.2913(3) 0.2400(3) 1.2874(6) 0.060(2) Uani 0.581(10) 1 d P B 1 H31A H -0.3395 0.2574 1.3157 0.072 Uiso 0.581(10) 1 calc PR B 1 H31B H -0.2597 0.2170 1.3608 0.072 Uiso 0.581(10) 1 calc PR B 1 C32 C -0.3198(11) 0.1921(11) 1.1805(17) 0.075(4) Uani 0.581(10) 1 d P B 1 H32A H -0.3516 0.1590 1.2123 0.113 Uiso 0.581(10) 1 calc PR B 1 H32B H -0.2729 0.1731 1.1529 0.113 Uiso 0.581(10) 1 calc PR B 1 H32C H -0.3531 0.2136 1.1079 0.113 Uiso 0.581(10) 1 calc PR B 1 C33 C 0.13993(19) -0.04240(15) 0.8334(3) 0.0614(8) Uani 1 1 d . . . H33A H 0.0889 -0.0388 0.8644 0.092 Uiso 1 1 calc R . . H33B H 0.1771 -0.0095 0.8729 0.092 Uiso 1 1 calc R . . H33C H 0.1638 -0.0840 0.8559 0.092 Uiso 1 1 calc R . . C34 C 0.07576(16) 0.04250(12) 0.6588(3) 0.0498(7) Uani 1 1 d . . . H34A H 0.0564 0.0546 0.5696 0.075 Uiso 1 1 calc R . . H34B H 0.1153 0.0735 0.6998 0.075 Uiso 1 1 calc R . . H34C H 0.0302 0.0410 0.7041 0.075 Uiso 1 1 calc R . . N1 N 0.49854(12) 0.01343(11) 0.7670(2) 0.0449(5) Uani 1 1 d . . . N2 N 0.06464(10) 0.23885(8) 1.11155(17) 0.0292(4) Uani 1 1 d . . . O1 O 0.39417(9) 0.13209(8) 0.91975(16) 0.0413(4) Uani 1 1 d . . . O3 O 0.16758(8) 0.13751(7) 0.92030(14) 0.0304(3) Uani 1 1 d . . . O4 O 0.28892(9) 0.20768(8) 1.03353(16) 0.0393(4) Uani 1 1 d . . . O5 O 0.05658(12) -0.07925(8) 0.61264(17) 0.0528(5) Uani 1 1 d . . . 02 O 0.27186(9) 0.06463(9) 0.80424(17) 0.0464(4) Uani 1 1 d . . . Cu1 Cu 0.280865(15) 0.136184(13) 0.91831(3) 0.03223(9) Uani 1 1 d . . . S1 S 0.12171(4) -0.03311(3) 0.66415(6) 0.03997(15) Uani 1 1 d . . . S2 S 0.50521(6) 0.29667(4) 0.98080(19) 0.0638(5) Uani 0.875(5) 1 d PD C 1 C35 C 0.4574(3) 0.2719(2) 0.8260(4) 0.0866(15) Uani 0.875(5) 1 d PD C 1 H35A H 0.4324 0.3083 0.7776 0.130 Uiso 0.875(5) 1 calc PR C 1 H35B H 0.4160 0.2404 0.8336 0.130 Uiso 0.875(5) 1 calc PR C 1 H35C H 0.4976 0.2532 0.7814 0.130 Uiso 0.875(5) 1 calc PR C 1 C36 C 0.4205(2) 0.3306(2) 1.0295(4) 0.0745(12) Uani 0.875(5) 1 d PD C 1 H36A H 0.4354 0.3453 1.1180 0.112 Uiso 0.875(5) 1 calc PR C 1 H36B H 0.3775 0.2990 1.0236 0.112 Uiso 0.875(5) 1 calc PR C 1 H36C H 0.4013 0.3665 0.9739 0.112 Uiso 0.875(5) 1 calc PR C 1 O6 O 0.5606(3) 0.35003(19) 0.9628(6) 0.0732(12) Uani 0.875(5) 1 d PD C 1 C13B C 0.8059(5) -0.0779(7) 0.6759(13) 0.073(3) Uani 0.448(14) 1 d PD A 2 H13B H 0.8148 -0.1097 0.7466 0.088 Uiso 0.448(14) 1 calc PR A 2 C15B C 0.8626(8) -0.0281(8) 0.7096(15) 0.085(4) Uani 0.448(14) 1 d P A 2 H15C H 0.8399 0.0103 0.6638 0.102 Uiso 0.448(14) 1 calc PR A 2 H15D H 0.9119 -0.0392 0.6763 0.102 Uiso 0.448(14) 1 calc PR A 2 C16B C 0.8868(11) -0.0121(10) 0.843(2) 0.061(5) Uani 0.448(14) 1 d P A 2 H16D H 0.9184 0.0270 0.8504 0.091 Uiso 0.448(14) 1 calc PR A 2 H16E H 0.9196 -0.0463 0.8871 0.091 Uiso 0.448(14) 1 calc PR A 2 H16F H 0.8388 -0.0060 0.8809 0.091 Uiso 0.448(14) 1 calc PR A 2 C14B C 0.8044(6) -0.1108(7) 0.5588(13) 0.055(3) Uani 0.448(14) 1 d P A 2 H14D H 0.7697 -0.1480 0.5561 0.082 Uiso 0.448(14) 1 calc PR A 2 H14E H 0.8592 -0.1241 0.5527 0.082 Uiso 0.448(14) 1 calc PR A 2 H14F H 0.7834 -0.0828 0.4870 0.082 Uiso 0.448(14) 1 calc PR A 2 C29B C -0.2637(6) 0.2682(5) 1.2054(9) 0.060(3) Uani 0.419(10) 1 d P B 2 H29B H -0.2921 0.3002 1.1443 0.072 Uiso 0.419(10) 1 calc PR B 2 C31B C -0.2651(5) 0.2898(5) 1.3376(11) 0.076(4) Uani 0.419(10) 1 d P B 2 H31C H -0.3216 0.2884 1.3508 0.091 Uiso 0.419(10) 1 calc PR B 2 H31D H -0.2340 0.2592 1.3976 0.091 Uiso 0.419(10) 1 calc PR B 2 C32B C -0.2330(17) 0.3536(14) 1.372(3) 0.070(5) Uani 0.419(10) 1 d P B 2 H32D H -0.2351 0.3620 1.4623 0.105 Uiso 0.419(10) 1 calc PR B 2 H32E H -0.2655 0.3850 1.3183 0.105 Uiso 0.419(10) 1 calc PR B 2 H32F H -0.1770 0.3561 1.3600 0.105 Uiso 0.419(10) 1 calc PR B 2 C30B C -0.3099(15) 0.2057(14) 1.183(3) 0.092(9) Uani 0.419(10) 1 d P B 2 H30D H -0.3113 0.1915 1.0953 0.139 Uiso 0.419(10) 1 calc PR B 2 H30E H -0.3651 0.2118 1.1976 0.139 Uiso 0.419(10) 1 calc PR B 2 H30F H -0.2829 0.1738 1.2429 0.139 Uiso 0.419(10) 1 calc PR B 2 S2B S 0.5091(6) 0.2975(5) 0.9094(13) 0.075(3) Uiso 0.125(5) 1 d PD C 2 C35B C 0.4116(14) 0.3081(18) 0.813(3) 0.098(12) Uiso 0.125(5) 1 d PD C 2 H35D H 0.3833 0.3423 0.8480 0.146 Uiso 0.125(5) 1 calc PR C 2 H35E H 0.3806 0.2689 0.8117 0.146 Uiso 0.125(5) 1 calc PR C 2 H35F H 0.4174 0.3189 0.7253 0.146 Uiso 0.125(5) 1 calc PR C 2 C36B C 0.4667(19) 0.2854(17) 1.053(2) 0.093(10) Uiso 0.125(5) 1 d PD C 2 H36D H 0.4976 0.3099 1.1233 0.139 Uiso 0.125(5) 1 calc PR C 2 H36E H 0.4693 0.2405 1.0750 0.139 Uiso 0.125(5) 1 calc PR C 2 H36F H 0.4104 0.2994 1.0370 0.139 Uiso 0.125(5) 1 calc PR C 2 O6B O 0.546(2) 0.3616(12) 0.938(4) 0.071(11) Uiso 0.125(5) 1 d PD C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0277(12) 0.0572(16) 0.0428(14) 0.0053(12) 0.0093(10) 0.0030(11) C2 0.0273(11) 0.0449(14) 0.0351(12) 0.0036(10) 0.0086(9) 0.0024(10) C3 0.0284(12) 0.0502(15) 0.0417(13) -0.0056(11) 0.0086(10) 0.0040(11) C4 0.0343(14) 0.071(2) 0.0673(19) -0.0249(15) 0.0101(13) 0.0018(13) C5 0.0424(15) 0.0672(19) 0.0582(17) -0.0155(15) 0.0132(13) 0.0112(14) C6 0.0283(13) 0.088(2) 0.089(2) -0.0193(19) 0.0147(14) -0.0040(14) C7 0.0331(13) 0.0718(19) 0.0433(15) 0.0091(13) 0.0142(11) 0.0212(13) C8 0.0540(18) 0.092(2) 0.0578(18) 0.0256(17) 0.0190(14) 0.0286(17) C9 0.060(2) 0.099(3) 0.082(2) 0.019(2) 0.0053(18) 0.045(2) C10 0.0449(16) 0.115(3) 0.0589(19) 0.0043(19) 0.0215(15) 0.0269(18) C11 0.0452(16) 0.109(3) 0.0599(19) 0.0218(18) 0.0236(14) 0.0254(18) C12 0.0428(15) 0.084(2) 0.0563(17) 0.0219(16) 0.0171(13) 0.0241(15) C13 0.028(3) 0.041(4) 0.074(5) 0.017(3) 0.029(3) 0.004(3) C14 0.166(12) 0.072(8) 0.246(18) -0.038(8) 0.173(12) 0.005(7) C15 0.028(3) 0.065(5) 0.072(5) 0.018(4) 0.016(3) 0.017(3) C16 0.056(5) 0.089(11) 0.087(8) -0.039(7) 0.019(5) -0.015(6) C17 0.0295(11) 0.0261(11) 0.0301(11) 0.0005(9) 0.0069(9) -0.0011(9) C18 0.0279(11) 0.0253(11) 0.0293(11) 0.0026(9) 0.0057(9) -0.0005(9) C19 0.0299(11) 0.0289(11) 0.0364(12) 0.0017(9) 0.0075(9) -0.0045(9) C20 0.0351(12) 0.0353(13) 0.0428(14) -0.0080(10) 0.0063(10) -0.0100(10) C21 0.0406(13) 0.0301(12) 0.0356(12) -0.0058(10) 0.0102(10) -0.0045(10) C22 0.0262(11) 0.0370(13) 0.0446(14) -0.0087(10) 0.0088(10) -0.0033(9) C23 0.0324(11) 0.0278(11) 0.0326(12) -0.0021(9) 0.0103(9) 0.0019(9) C24 0.0360(12) 0.0284(12) 0.0398(13) 0.0054(10) 0.0112(10) 0.0068(9) C25 0.0402(13) 0.0411(14) 0.0490(15) 0.0071(11) 0.0199(11) 0.0021(11) C26 0.0429(15) 0.0584(17) 0.0653(18) 0.0130(14) 0.0247(13) 0.0187(13) C27 0.0504(16) 0.0456(15) 0.0586(17) 0.0135(13) 0.0164(13) 0.0232(13) C28 0.0454(14) 0.0319(12) 0.0387(13) 0.0055(10) 0.0122(11) 0.0044(10) C29 0.031(2) 0.049(3) 0.057(4) -0.016(3) 0.021(3) 0.004(2) C30 0.038(5) 0.090(11) 0.112(8) -0.052(6) 0.033(4) 0.002(6) C31 0.030(2) 0.064(4) 0.091(5) -0.014(3) 0.023(3) -0.004(2) C32 0.062(7) 0.070(8) 0.090(8) -0.022(6) 0.002(4) -0.016(5) C33 0.073(2) 0.0593(18) 0.0455(16) 0.0068(14) -0.0044(14) -0.0193(16) C34 0.0513(16) 0.0327(13) 0.0619(17) -0.0043(12) 0.0014(13) -0.0006(12) N1 0.0319(11) 0.0604(14) 0.0442(12) 0.0027(10) 0.0121(9) 0.0130(10) N2 0.0305(9) 0.0266(9) 0.0322(10) -0.0002(8) 0.0105(8) 0.0007(8) O1 0.0246(8) 0.0460(10) 0.0552(10) -0.0089(8) 0.0121(7) -0.0037(7) O3 0.0244(7) 0.0320(8) 0.0355(8) -0.0067(7) 0.0075(6) 0.0006(6) O4 0.0268(8) 0.0408(9) 0.0513(10) -0.0084(8) 0.0098(7) -0.0067(7) O5 0.0687(13) 0.0336(10) 0.0505(11) -0.0057(8) -0.0036(9) -0.0052(9) 02 0.0244(8) 0.0601(11) 0.0547(11) -0.0194(9) 0.0076(7) 0.0016(8) Cu1 0.02326(14) 0.03670(16) 0.03765(16) -0.00168(12) 0.00798(11) -0.00068(11) S1 0.0429(3) 0.0362(3) 0.0408(3) -0.0004(3) 0.0079(3) 0.0029(3) S2 0.0558(6) 0.0405(5) 0.0906(12) 0.0093(5) 0.0017(5) -0.0092(4) C35 0.095(3) 0.069(3) 0.094(3) -0.027(2) 0.013(3) -0.029(3) C36 0.068(3) 0.072(3) 0.086(3) -0.002(2) 0.020(2) -0.019(2) O6 0.057(2) 0.0511(18) 0.112(3) -0.007(2) 0.015(2) -0.0214(18) C13B 0.063(5) 0.083(8) 0.075(7) -0.014(6) 0.015(4) -0.027(6) C15B 0.088(8) 0.075(8) 0.089(9) -0.036(7) 0.011(7) -0.009(6) C16B 0.029(5) 0.068(11) 0.078(8) 0.000(8) -0.007(5) 0.005(6) C14B 0.034(4) 0.069(7) 0.070(5) -0.041(5) 0.034(4) -0.021(4) C29B 0.076(6) 0.058(6) 0.052(5) -0.007(4) 0.025(5) 0.021(5) C31B 0.056(5) 0.082(8) 0.091(7) -0.018(5) 0.015(5) 0.014(5) C32B 0.044(10) 0.085(12) 0.079(8) -0.044(7) 0.010(6) 0.007(6) C30B 0.042(7) 0.085(15) 0.154(16) -0.062(10) 0.031(8) -0.012(8) _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 C1 N1 1.382(3) . ? C1 C2 1.389(3) . ? C1 C6 1.502(4) . ? C2 O1 1.326(3) . ? C2 C3 1.429(3) . ? C3 02 1.300(3) . ? C3 C4 1.399(4) . ? C4 C5 1.366(4) . ? C4 H4 0.9500 . ? C5 N1 1.349(4) . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.378(4) . ? C7 C12 1.383(4) . ? C7 N1 1.457(3) . ? C8 C9 1.403(4) . ? C8 H8 0.9500 . ? C9 C10 1.389(5) . ? C9 H9 0.9500 . ? C10 C11 1.382(5) . ? C10 C13 1.573(5) . ? C10 C13B 1.607(8) . ? C11 C12 1.376(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C15 1.521(13) . ? C13 C14 1.531(18) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.52(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N2 1.382(3) . ? C17 C18 1.387(3) . ? C17 C22 1.495(3) . ? C18 O3 1.323(2) . ? C18 C19 1.434(3) . ? C19 O4 1.304(3) . ? C19 C20 1.400(3) . ? C20 C21 1.369(3) . ? C20 H20 0.9500 . ? C21 N2 1.356(3) . ? C21 H21 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.384(3) . ? C23 C28 1.388(3) . ? C23 N2 1.458(3) . ? C24 C25 1.382(3) . ? C24 H24 0.9500 . ? C25 C26 1.395(4) . ? C25 H25 0.9500 . ? C26 C27 1.388(4) . ? C26 C29 1.546(6) . ? C26 C29B 1.650(10) . ? C27 C28 1.382(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.48(2) . ? C29 C31 1.522(9) . ? C29 H29 1.0000 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C32 1.54(2) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 S1 1.782(3) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 S1 1.776(3) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O1 Cu1 1.9119(15) . ? O3 Cu1 1.9165(14) . ? O4 Cu1 1.9378(16) . ? O5 S1 1.4975(18) . ? 02 Cu1 1.9306(17) . ? S2 O6 1.502(3) . ? S2 C36 1.762(4) . ? S2 C35 1.776(4) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C13B C14B 1.423(17) . ? C13B C15B 1.425(18) . ? C13B H13B 1.0000 . ? C15B C16B 1.44(3) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C29B C31B 1.484(15) . ? C29B C30B 1.53(3) . ? C29B H29B 1.0000 . ? C31B C32B 1.48(3) . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? C32B H32D 0.9800 . ? C32B H32E 0.9800 . ? C32B H32F 0.9800 . ? C30B H30D 0.9800 . ? C30B H30E 0.9800 . ? C30B H30F 0.9800 . ? S2B O6B 1.499(17) . ? S2B C35B 1.787(17) . ? S2B C36B 1.819(18) . ? C35B H35D 0.9800 . ? C35B H35E 0.9800 . ? C35B H35F 0.9800 . ? C36B H36D 0.9800 . ? C36B H36E 0.9800 . ? C36B H36F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 119.0(2) . . ? N1 C1 C6 119.9(2) . . ? C2 C1 C6 121.1(2) . . ? O1 C2 C1 123.1(2) . . ? O1 C2 C3 117.18(19) . . ? C1 C2 C3 119.7(2) . . ? 02 C3 C4 124.9(2) . . ? 02 C3 C2 116.9(2) . . ? C4 C3 C2 118.1(2) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 120.9(3) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C12 120.6(2) . . ? C8 C7 N1 120.0(2) . . ? C12 C7 N1 119.3(2) . . ? C7 C8 C9 118.5(3) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 121.6(3) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 117.8(3) . . ? C11 C10 C13 115.2(4) . . ? C9 C10 C13 127.0(4) . . ? C11 C10 C13B 138.5(7) . . ? C9 C10 C13B 102.9(7) . . ? C13 C10 C13B 25.0(4) . . ? C12 C11 C10 121.7(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C15 C13 C14 112.3(10) . . ? C15 C13 C10 110.8(5) . . ? C14 C13 C10 101.4(7) . . ? C15 C13 H13 110.7 . . ? C14 C13 H13 110.7 . . ? C10 C13 H13 110.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C13 112.3(11) . . ? C16 C15 H15A 109.1 . . ? C13 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? C13 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 118.98(19) . . ? N2 C17 C22 119.79(18) . . ? C18 C17 C22 121.23(19) . . ? O3 C18 C17 122.76(18) . . ? O3 C18 C19 117.23(18) . . ? C17 C18 C19 120.01(19) . . ? O4 C19 C20 124.6(2) . . ? O4 C19 C18 117.23(19) . . ? C20 C19 C18 118.1(2) . . ? C21 C20 C19 120.2(2) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? N2 C21 C20 121.2(2) . . ? N2 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 120.7(2) . . ? C24 C23 N2 119.84(19) . . ? C28 C23 N2 119.44(19) . . ? C25 C24 C23 119.4(2) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 121.5(2) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C27 C26 C25 117.5(2) . . ? C27 C26 C29 117.7(3) . . ? C25 C26 C29 123.2(3) . . ? C27 C26 C29B 122.9(4) . . ? C25 C26 C29B 116.7(4) . . ? C29 C26 C29B 30.0(3) . . ? C28 C27 C26 122.3(2) . . ? C28 C27 H27 118.9 . . ? C26 C27 H27 118.9 . . ? C27 C28 C23 118.6(2) . . ? C27 C28 H28 120.7 . . ? C23 C28 H28 120.7 . . ? C30 C29 C31 111.7(11) . . ? C30 C29 C26 114.2(9) . . ? C31 C29 C26 111.2(5) . . ? C30 C29 H29 106.4 . . ? C31 C29 H29 106.4 . . ? C26 C29 H29 106.4 . . ? 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 117.3(9) . . ? C29 C31 H31A 108.0 . . ? C32 C31 H31A 108.0 . . ? C29 C31 H31B 108.0 . . ? C32 C31 H31B 108.0 . . ? H31A C31 H31B 107.2 . . ? 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 . . ? S1 C33 H33A 109.5 . . ? S1 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? S1 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? S1 C34 H34A 109.5 . . ? S1 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? S1 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C5 N1 C1 121.8(2) . . ? C5 N1 C7 117.6(2) . . ? C1 N1 C7 120.6(2) . . ? C21 N2 C17 121.56(18) . . ? C21 N2 C23 117.91(18) . . ? C17 N2 C23 120.52(17) . . ? C2 O1 Cu1 109.54(13) . . ? C18 O3 Cu1 109.53(12) . . ? C19 O4 Cu1 109.56(13) . . ? C3 02 Cu1 110.04(15) . . ? O1 Cu1 O3 177.94(7) . . ? O1 Cu1 02 86.11(7) . . ? O3 Cu1 02 93.17(6) . . ? O1 Cu1 O4 94.41(7) . . ? O3 Cu1 O4 86.30(6) . . ? 02 Cu1 O4 179.39(7) . . ? O5 S1 C34 106.86(12) . . ? O5 S1 C33 106.06(12) . . ? C34 S1 C33 97.17(15) . . ? O6 S2 C36 106.8(2) . . ? O6 S2 C35 106.9(3) . . ? C36 S2 C35 98.0(2) . . ? C14B C13B C15B 119.0(14) . . ? C14B C13B C10 118.2(8) . . ? C15B C13B C10 94.9(11) . . ? C14B C13B H13B 107.9 . . ? C15B C13B H13B 107.9 . . ? C10 C13B H13B 107.9 . . ? C13B C15B C16B 118.5(19) . . ? C13B C15B H15C 107.7 . . ? C16B C15B H15C 107.7 . . ? C13B C15B H15D 107.7 . . ? C16B C15B H15D 107.7 . . ? H15C C15B H15D 107.1 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.4 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C13B C14B H14D 109.5 . . ? C13B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C31B C29B C30B 108.4(13) . . ? C31B C29B C26 100.9(8) . . ? C30B C29B C26 121.2(10) . . ? C31B C29B H29B 108.5 . . ? C30B C29B H29B 108.5 . . ? C26 C29B H29B 108.5 . . ? C32B C31B C29B 116.9(15) . . ? C32B C31B H31C 108.1 . . ? C29B C31B H31C 108.1 . . ? C32B C31B H31D 108.1 . . ? C29B C31B H31D 108.1 . . ? H31C C31B H31D 107.3 . . ? C31B C32B H32D 109.5 . . ? C31B C32B H32E 109.5 . . ? H32D C32B H32E 109.5 . . ? C31B C32B H32F 109.5 . . ? H32D C32B H32F 109.5 . . ? H32E C32B H32F 109.5 . . ? C29B C30B H30D 109.5 . . ? C29B C30B H30E 109.5 . . ? H30D C30B H30E 109.5 . . ? C29B C30B H30F 109.5 . . ? H30D C30B H30F 109.5 . . ? H30E C30B H30F 109.5 . . ? O6B S2B C35B 107.8(16) . . ? O6B S2B C36B 99.5(16) . . ? C35B S2B C36B 92.2(13) . . ? S2B C35B H35D 109.5 . . ? S2B C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? S2B C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? S2B C36B H36D 109.5 . . ? S2B C36B H36E 109.5 . . ? H36D C36B H36E 109.5 . . ? S2B C36B H36F 109.5 . . ? H36D C36B H36F 109.5 . . ? H36E C36B H36F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 O1 -179.2(2) . . . . ? C6 C1 C2 O1 2.3(4) . . . . ? N1 C1 C2 C3 2.1(3) . . . . ? C6 C1 C2 C3 -176.4(3) . . . . ? O1 C2 C3 02 1.0(3) . . . . ? C1 C2 C3 02 179.7(2) . . . . ? O1 C2 C3 C4 -178.3(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? 02 C3 C4 C5 178.4(3) . . . . ? C2 C3 C4 C5 -2.4(4) . . . . ? C3 C4 C5 N1 1.8(5) . . . . ? C12 C7 C8 C9 0.8(5) . . . . ? N1 C7 C8 C9 177.2(3) . . . . ? C7 C8 C9 C10 1.2(6) . . . . ? C8 C9 C10 C11 -1.4(6) . . . . ? C8 C9 C10 C13 -179.8(5) . . . . ? C8 C9 C10 C13B -172.7(5) . . . . ? C9 C10 C11 C12 -0.2(6) . . . . ? C13 C10 C11 C12 178.4(5) . . . . ? C13B C10 C11 C12 166.9(7) . . . . ? C10 C11 C12 C7 2.1(5) . . . . ? C8 C7 C12 C11 -2.4(5) . . . . ? N1 C7 C12 C11 -178.8(3) . . . . ? C11 C10 C13 C15 127.1(7) . . . . ? C9 C10 C13 C15 -54.5(9) . . . . ? C13B C10 C13 C15 -71.1(13) . . . . ? C11 C10 C13 C14 -113.5(9) . . . . ? C9 C10 C13 C14 64.9(10) . . . . ? C13B C10 C13 C14 48.4(16) . . . . ? C14 C13 C15 C16 -176.9(11) . . . . ? C10 C13 C15 C16 -64.3(13) . . . . ? N2 C17 C18 O3 178.43(18) . . . . ? C22 C17 C18 O3 -1.6(3) . . . . ? N2 C17 C18 C19 -1.5(3) . . . . ? C22 C17 C18 C19 178.5(2) . . . . ? O3 C18 C19 O4 0.8(3) . . . . ? C17 C18 C19 O4 -179.26(19) . . . . ? O3 C18 C19 C20 -178.35(19) . . . . ? C17 C18 C19 C20 1.6(3) . . . . ? O4 C19 C20 C21 -179.9(2) . . . . ? C18 C19 C20 C21 -0.8(3) . . . . ? C19 C20 C21 N2 -0.1(4) . . . . ? C28 C23 C24 C25 0.0(3) . . . . ? N2 C23 C24 C25 179.9(2) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C24 C25 C26 C27 -0.4(4) . . . . ? C24 C25 C26 C29 -165.3(4) . . . . ? C24 C25 C26 C29B 160.7(5) . . . . ? C25 C26 C27 C28 0.3(5) . . . . ? C29 C26 C27 C28 166.0(4) . . . . ? C29B C26 C27 C28 -159.6(5) . . . . ? C26 C27 C28 C23 0.0(4) . . . . ? C24 C23 C28 C27 -0.2(4) . . . . ? N2 C23 C28 C27 180.0(2) . . . . ? C27 C26 C29 C30 -79.1(11) . . . . ? C25 C26 C29 C30 85.8(11) . . . . ? C29B C26 C29 C30 172.5(15) . . . . ? C27 C26 C29 C31 153.5(4) . . . . ? C25 C26 C29 C31 -41.6(7) . . . . ? C29B C26 C29 C31 45.0(8) . . . . ? C30 C29 C31 C32 176.9(11) . . . . ? C26 C29 C31 C32 -54.3(10) . . . . ? C4 C5 N1 C1 0.9(4) . . . . ? C4 C5 N1 C7 -176.6(3) . . . . ? C2 C1 N1 C5 -2.8(4) . . . . ? C6 C1 N1 C5 175.7(3) . . . . ? C2 C1 N1 C7 174.6(2) . . . . ? C6 C1 N1 C7 -6.9(4) . . . . ? C8 C7 N1 C5 -75.5(4) . . . . ? C12 C7 N1 C5 100.9(3) . . . . ? C8 C7 N1 C1 107.0(3) . . . . ? C12 C7 N1 C1 -76.6(3) . . . . ? C20 C21 N2 C17 0.2(3) . . . . ? C20 C21 N2 C23 178.9(2) . . . . ? C18 C17 N2 C21 0.6(3) . . . . ? C22 C17 N2 C21 -179.4(2) . . . . ? C18 C17 N2 C23 -178.03(18) . . . . ? C22 C17 N2 C23 2.0(3) . . . . ? C24 C23 N2 C21 -102.2(2) . . . . ? C28 C23 N2 C21 77.6(3) . . . . ? C24 C23 N2 C17 76.5(3) . . . . ? C28 C23 N2 C17 -103.7(2) . . . . ? C1 C2 O1 Cu1 -176.25(19) . . . . ? C3 C2 O1 Cu1 2.4(3) . . . . ? C17 C18 O3 Cu1 -177.78(16) . . . . ? C19 C18 O3 Cu1 2.1(2) . . . . ? C20 C19 O4 Cu1 175.84(19) . . . . ? C18 C19 O4 Cu1 -3.3(2) . . . . ? C4 C3 02 Cu1 175.4(2) . . . . ? C2 C3 02 Cu1 -3.8(3) . . . . ? C2 O1 Cu1 O3 66.1(19) . . . . ? C2 O1 Cu1 02 -3.54(15) . . . . ? C2 O1 Cu1 O4 176.14(15) . . . . ? C18 O3 Cu1 O1 107.1(19) . . . . ? C18 O3 Cu1 02 176.62(13) . . . . ? C18 O3 Cu1 O4 -3.08(13) . . . . ? C3 02 Cu1 O1 4.09(17) . . . . ? C3 02 Cu1 O3 -173.97(16) . . . . ? C3 02 Cu1 O4 -144(8) . . . . ? C19 O4 Cu1 O1 -174.54(14) . . . . ? C19 O4 Cu1 O3 3.52(14) . . . . ? C19 O4 Cu1 02 -26(8) . . . . ? C11 C10 C13B C14B -60.8(16) . . . . ? C9 C10 C13B C14B 107.5(13) . . . . ? C13 C10 C13B C14B -86(2) . . . . ? C11 C10 C13B C15B 65.9(13) . . . . ? C9 C10 C13B C15B -125.8(12) . . . . ? C13 C10 C13B C15B 40.7(14) . . . . ? C14B C13B C15B C16B -155.8(13) . . . . ? C10 C13B C15B C16B 78(2) . . . . ? C27 C26 C29B C31B -116.5(6) . . . . ? C25 C26 C29B C31B 83.5(7) . . . . ? C29 C26 C29B C31B -27.3(7) . . . . ? C27 C26 C29B C30B 123.9(14) . . . . ? C25 C26 C29B C30B -36.1(15) . . . . ? C29 C26 C29B C30B -146.8(18) . . . . ? C30B C29B C31B C32B -172.2(15) . . . . ? C26 C29B C31B C32B 59.4(13) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.864 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.058