# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Zhen-Feng Chen' _publ_contact_author_email CHENZFUBC@YAHOO.COM _publ_section_title ; Antitumour activity of the Traditional Chinese Medicine (TCM) plumbagin in its copper chemistry ; loop_ _publ_author_name 'Zhen-Feng Chen' 'Hong Liang' 'Li-Min Liu' 'Hua-Gang Liu' 'Yan-Cheng Liu' 'Chris Orvig' 'Yan Peng' ; M.-X.Tan ; 'Heng-Shan Wang' 'Bin Yang' # Attachment 'CCDC-No725715.cif' data_xb1734 _database_code_depnum_ccdc_archive 'CCDC 725715' #TrackingRef 'CCDC-No725715.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Cu O8' _chemical_formula_weight 473.90 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.576(4) _cell_length_b 10.0549(18) _cell_length_c 9.3266(17) _cell_angle_alpha 90.00 _cell_angle_beta 109.319(3) _cell_angle_gamma 90.00 _cell_volume 1909.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 757 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 19.10 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7339 _exptl_absorpt_correction_T_max 0.8718 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4662 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1684 _reflns_number_gt 1084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+1.6913P] 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 1684 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Cu1 Cu 1.0000 0.0000 1.0000 0.0515(4) Uani 1 2 d S . . O1 O 0.96439(15) 0.1524(3) 0.8791(3) 0.0526(9) Uani 1 1 d . . . O2 O 0.94837(15) -0.1193(3) 0.8532(3) 0.0529(9) Uani 1 1 d . . . O3 O 0.77708(18) 0.2160(4) 0.3402(4) 0.0766(11) Uani 1 1 d . . . C1 C 0.9203(2) 0.1574(5) 0.7486(5) 0.0481(12) Uani 1 1 d . . . C2 C 0.9037(2) 0.2890(5) 0.6847(6) 0.0538(13) Uani 1 1 d . . . H2 H 0.9255 0.3619 0.7402 0.065 Uiso 1 1 calc R . . C3 C 0.8579(3) 0.3103(5) 0.5481(6) 0.0564(13) Uani 1 1 d . . . C4 C 0.8222(2) 0.1962(6) 0.4604(5) 0.0534(13) Uani 1 1 d . . . C5 C 0.8402(2) 0.0612(5) 0.5179(5) 0.0460(12) Uani 1 1 d . . . C6 C 0.8100(2) -0.0456(6) 0.4340(6) 0.0563(14) Uani 1 1 d . . . H6 H 0.7783 -0.0319 0.3395 0.068 Uiso 1 1 calc R . . C7 C 0.8257(2) -0.1745(6) 0.4866(6) 0.0587(14) Uani 1 1 d . . . H7 H 0.8050 -0.2465 0.4274 0.070 Uiso 1 1 calc R . . C8 C 0.8724(2) -0.1950(6) 0.6281(6) 0.0569(13) Uani 1 1 d . . . H8 H 0.8822 -0.2816 0.6634 0.068 Uiso 1 1 calc R . . C9 C 0.9053(2) -0.0889(5) 0.7200(5) 0.0488(12) Uani 1 1 d . . . C10 C 0.8896(2) 0.0431(5) 0.6650(5) 0.0465(12) Uani 1 1 d . . . C11 C 0.8416(3) 0.4468(6) 0.4809(7) 0.0726(17) Uani 1 1 d . . . H11A H 0.7989 0.4724 0.4822 0.109 Uiso 1 1 calc R . . H11B H 0.8417 0.4462 0.3781 0.109 Uiso 1 1 calc R . . H11C H 0.8738 0.5091 0.5395 0.109 Uiso 1 1 calc R . . O4 O 1.0139(2) 0.4062(4) 1.1164(4) 0.0799(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0483(6) 0.0681(6) 0.0305(5) -0.0030(4) 0.0029(4) 0.0001(4) O1 0.0503(19) 0.066(2) 0.0319(17) -0.0004(16) 0.0013(15) 0.0008(17) O2 0.058(2) 0.061(2) 0.0294(17) -0.0037(15) 0.0012(16) -0.0040(17) O3 0.069(2) 0.085(3) 0.049(2) 0.006(2) -0.0152(19) 0.005(2) C1 0.040(3) 0.065(3) 0.036(3) -0.005(2) 0.009(2) -0.002(2) C2 0.054(3) 0.054(3) 0.045(3) -0.003(2) 0.005(2) 0.003(2) C3 0.051(3) 0.070(4) 0.044(3) 0.007(3) 0.011(2) 0.013(3) C4 0.042(3) 0.082(4) 0.035(3) -0.002(3) 0.010(2) 0.003(3) C5 0.036(3) 0.066(3) 0.032(2) 0.000(2) 0.005(2) -0.001(2) C6 0.042(3) 0.086(4) 0.033(3) -0.004(3) 0.003(2) -0.006(3) C7 0.053(3) 0.071(4) 0.045(3) -0.009(3) 0.007(3) -0.007(3) C8 0.056(3) 0.066(3) 0.043(3) -0.003(3) 0.010(2) -0.002(3) C9 0.044(3) 0.069(4) 0.033(3) -0.006(2) 0.013(2) -0.004(2) C10 0.039(3) 0.064(3) 0.034(2) 0.000(2) 0.008(2) -0.002(2) C11 0.063(4) 0.073(4) 0.063(4) 0.008(3) -0.004(3) 0.007(3) O4 0.096(3) 0.077(3) 0.064(3) 0.000(2) 0.022(2) 0.001(2) _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 Cu1 O2 1.883(3) . ? Cu1 O2 1.883(3) 5_757 ? Cu1 O1 1.907(3) 5_757 ? Cu1 O1 1.907(3) . ? O1 C1 1.274(5) . ? O2 C9 1.318(5) . ? O3 C4 1.233(6) . ? C1 C10 1.423(7) . ? C1 C2 1.447(7) . ? C2 C3 1.345(7) . ? C2 H2 0.9300 . ? C3 C4 1.470(7) . ? C3 C11 1.502(7) . ? C4 C5 1.464(7) . ? C5 C6 1.362(7) . ? C5 C10 1.443(6) . ? C6 C7 1.387(7) . ? C6 H6 0.9300 . ? C7 C8 1.386(7) . ? C7 H7 0.9300 . ? C8 C9 1.405(7) . ? C8 H8 0.9300 . ? C9 C10 1.423(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 O2 Cu1 O2 180.000(1) . 5_757 ? O2 Cu1 O1 86.79(14) . 5_757 ? O2 Cu1 O1 93.21(14) 5_757 5_757 ? O2 Cu1 O1 93.21(14) . . ? O2 Cu1 O1 86.79(14) 5_757 . ? O1 Cu1 O1 180.000(1) 5_757 . ? C1 O1 Cu1 128.6(3) . . ? C9 O2 Cu1 126.9(3) . . ? O1 C1 C10 123.8(5) . . ? O1 C1 C2 115.8(5) . . ? C10 C1 C2 120.4(4) . . ? C3 C2 C1 122.6(5) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 C11 122.5(5) . . ? C4 C3 C11 118.3(5) . . ? O3 C4 C5 121.1(5) . . ? O3 C4 C3 119.4(5) . . ? C5 C4 C3 119.5(4) . . ? C6 C5 C10 120.6(5) . . ? C6 C5 C4 120.2(4) . . ? C10 C5 C4 119.2(5) . . ? C5 C6 C7 121.3(5) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 119.4(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 122.0(5) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? O2 C9 C8 117.1(5) . . ? O2 C9 C10 124.4(4) . . ? C8 C9 C10 118.5(4) . . ? C9 C10 C1 122.9(4) . . ? C9 C10 C5 118.2(5) . . ? C1 C10 C5 118.8(5) . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 O2 Cu1 O1 C1 1.5(4) . . . . ? O2 Cu1 O1 C1 -178.5(4) 5_757 . . . ? O1 Cu1 O2 C9 179.9(4) 5_757 . . . ? O1 Cu1 O2 C9 -0.1(4) . . . . ? Cu1 O1 C1 C10 -1.7(7) . . . . ? Cu1 O1 C1 C2 -179.7(3) . . . . ? O1 C1 C2 C3 -179.8(4) . . . . ? C10 C1 C2 C3 2.1(7) . . . . ? C1 C2 C3 C4 1.2(8) . . . . ? C1 C2 C3 C11 -178.9(5) . . . . ? C2 C3 C4 O3 175.0(5) . . . . ? C11 C3 C4 O3 -4.9(7) . . . . ? C2 C3 C4 C5 -4.5(7) . . . . ? C11 C3 C4 C5 175.7(5) . . . . ? O3 C4 C5 C6 4.2(7) . . . . ? C3 C4 C5 C6 -176.4(4) . . . . ? O3 C4 C5 C10 -174.9(4) . . . . ? C3 C4 C5 C10 4.5(6) . . . . ? C10 C5 C6 C7 -0.1(7) . . . . ? C4 C5 C6 C7 -179.2(5) . . . . ? C5 C6 C7 C8 0.8(8) . . . . ? C6 C7 C8 C9 -0.9(8) . . . . ? Cu1 O2 C9 C8 179.8(3) . . . . ? Cu1 O2 C9 C10 -1.1(6) . . . . ? C7 C8 C9 O2 179.4(4) . . . . ? C7 C8 C9 C10 0.3(7) . . . . ? O2 C9 C10 C1 1.3(7) . . . . ? C8 C9 C10 C1 -179.6(4) . . . . ? O2 C9 C10 C5 -178.7(4) . . . . ? C8 C9 C10 C5 0.4(6) . . . . ? O1 C1 C10 C9 0.2(7) . . . . ? C2 C1 C10 C9 178.1(4) . . . . ? O1 C1 C10 C5 -179.9(4) . . . . ? C2 C1 C10 C5 -1.9(7) . . . . ? C6 C5 C10 C9 -0.5(7) . . . . ? C4 C5 C10 C9 178.6(4) . . . . ? C6 C5 C10 C1 179.6(4) . . . . ? C4 C5 C10 C1 -1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.411 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.074 # Attachment '725716.cif' data_xb1973m _database_code_depnum_ccdc_archive 'CCDC 725716' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 Cu N3 O9' _chemical_formula_weight 522.95 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.684(8) _cell_length_b 10.357(9) _cell_length_c 13.036(11) _cell_angle_alpha 72.472(13) _cell_angle_beta 83.105(13) _cell_angle_gamma 88.979(13) _cell_volume 1109.7(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2099 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 25.05 _exptl_crystal_description block _exptl_crystal_colour dark-red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 538 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8345 _exptl_absorpt_correction_T_max 0.9029 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5332 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3794 _reflns_number_gt 2826 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1466P)^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_number_reflns 3794 _refine_ls_number_parameters 323 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1960 _refine_ls_wR_factor_gt 0.1844 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.025 _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 Cu1 Cu 0.83973(6) 0.17622(6) 0.73565(4) 0.0460(3) Uani 1 1 d . . . N1 N 0.7571(4) 0.0447(4) 0.8777(3) 0.0467(9) Uani 1 1 d . . . N2 N 0.9463(4) 0.2488(4) 0.8329(3) 0.0467(9) Uani 1 1 d . . . N3 N 0.5847(6) 0.2879(7) 0.2129(5) 0.0831(16) Uani 1 1 d D . . O1 O 0.9468(4) 0.2936(4) 0.6071(2) 0.0527(8) Uani 1 1 d . . . O2 O 0.7385(3) 0.0826(4) 0.6549(2) 0.0484(8) Uani 1 1 d . . . O3 O 0.9262(4) 0.0037(4) 0.2755(2) 0.0553(9) Uani 1 1 d . . . O4 O 0.6334(6) 0.3227(5) 0.7513(4) 0.0784(12) Uani 1 1 d D . . O5 O 0.6661(6) 0.4519(6) 0.9126(4) 0.1037(16) Uani 1 1 d . . . O6 O 0.3715(17) 0.498(3) 0.612(2) 0.207(15) Uani 0.40 1 d P . . O6' O 0.494(2) 0.5308(19) 0.6042(11) 0.198(8) Uani 0.60 1 d P . . C1 C 0.7817(5) 0.0775(5) 0.5612(3) 0.0427(10) Uani 1 1 d . . . C2 C 0.8744(5) 0.0349(5) 0.3568(3) 0.0441(10) Uani 1 1 d . . . C3 C 0.9714(5) 0.2712(5) 0.5149(3) 0.0457(11) Uani 1 1 d . . . C4 C 0.9000(5) 0.1659(5) 0.4880(3) 0.0399(10) Uani 1 1 d . . . C5 C 0.9453(5) 0.1446(5) 0.3856(3) 0.0435(10) Uani 1 1 d . . . C6 C 0.9072(5) 0.1882(5) 0.9386(4) 0.0461(11) Uani 1 1 d . . . C7 C 0.7419(5) -0.0418(5) 0.4300(3) 0.0469(11) Uani 1 1 d . . . C8 C 1.0560(6) 0.2286(6) 0.3119(3) 0.0533(12) Uani 1 1 d . . . H8 H 1.0866 0.2137 0.2456 0.064 Uiso 1 1 calc R . . C9 C 0.6648(5) -0.0619(5) 0.8922(4) 0.0496(11) Uani 1 1 d . . . H9 H 0.6348 -0.0796 0.8315 0.059 Uiso 1 1 calc R . . C10 C 0.8029(5) 0.0685(5) 0.9653(3) 0.0439(11) Uani 1 1 d . . . C11 C 0.7534(5) -0.0126(6) 1.0681(4) 0.0549(13) Uani 1 1 d . . . H11 H 0.7854 0.0060 1.1278 0.066 Uiso 1 1 calc R . . C12 C 0.7031(5) -0.0194(5) 0.5254(3) 0.0448(11) Uani 1 1 d . . . H12 H 0.6204 -0.0693 0.5713 0.054 Uiso 1 1 calc R . . C13 C 1.1207(6) 0.3334(6) 0.3361(4) 0.0591(13) Uani 1 1 d . . . H13 H 1.1937 0.3901 0.2852 0.071 Uiso 1 1 calc R . . C14 C 0.6122(6) -0.1469(6) 0.9929(4) 0.0576(13) Uani 1 1 d . . . H14 H 0.5475 -0.2207 1.0006 0.069 Uiso 1 1 calc R . . C15 C 1.0801(6) 0.3570(6) 0.4342(4) 0.0558(12) Uani 1 1 d . . . H15 H 1.1246 0.4303 0.4479 0.067 Uiso 1 1 calc R . . C16 C 0.6575(6) -0.1202(6) 1.0821(4) 0.0598(14) Uani 1 1 d . . . H16 H 0.6227 -0.1754 1.1515 0.072 Uiso 1 1 calc R . . C17 C 0.9657(6) 0.2337(6) 1.0169(4) 0.0584(13) Uani 1 1 d . . . H17 H 0.9388 0.1898 1.0903 0.070 Uiso 1 1 calc R . . C18 C 1.0429(6) 0.3572(6) 0.8009(4) 0.0604(13) Uani 1 1 d . . . H18 H 1.0698 0.3985 0.7271 0.072 Uiso 1 1 calc R . . C19 C 0.6623(6) -0.1443(6) 0.3943(4) 0.0628(14) Uani 1 1 d . . . H19A H 0.5944 -0.2001 0.4542 0.094 Uiso 1 1 calc R . . H19B H 0.7383 -0.1997 0.3691 0.094 Uiso 1 1 calc R . . H19C H 0.6030 -0.0989 0.3367 0.094 Uiso 1 1 calc R . . C20 C 1.0637(7) 0.3445(6) 0.9831(4) 0.0667(15) Uani 1 1 d . . . H20 H 1.1040 0.3767 1.0339 0.080 Uiso 1 1 calc R . . C21 C 1.1032(7) 0.4089(6) 0.8730(5) 0.0684(15) Uani 1 1 d . . . H21 H 1.1686 0.4849 0.8490 0.082 Uiso 1 1 calc R . . H4A H 0.611(7) 0.377(6) 0.691(3) 0.080 Uiso 1 1 d D . . H4B H 0.630(8) 0.362(6) 0.799(4) 0.080 Uiso 1 1 d D . . O7 O 0.6002(13) 0.3809(11) 0.1426(8) 0.233(6) Uani 1 1 d D . . O8 O 0.6292(14) 0.1822(14) 0.2137(13) 0.291(8) Uani 1 1 d D . . O9 O 0.5604(19) 0.2728(14) 0.3086(8) 0.282(7) Uani 1 1 d 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 Cu1 0.0477(4) 0.0587(5) 0.0349(3) -0.0203(2) -0.0012(2) -0.0038(3) N1 0.0404(19) 0.064(3) 0.0406(19) -0.0242(17) -0.0018(15) 0.0029(18) N2 0.045(2) 0.055(3) 0.0430(19) -0.0197(17) -0.0044(16) 0.0019(18) N3 0.067(3) 0.098(5) 0.077(4) -0.020(3) 0.008(3) 0.005(3) O1 0.064(2) 0.053(2) 0.0458(17) -0.0258(14) 0.0008(14) -0.0044(16) O2 0.0444(16) 0.068(2) 0.0354(15) -0.0214(14) 0.0031(12) -0.0052(15) O3 0.0588(19) 0.074(2) 0.0405(17) -0.0286(16) -0.0051(14) 0.0023(17) O4 0.083(3) 0.083(3) 0.071(3) -0.028(2) -0.005(2) 0.016(2) O5 0.109(4) 0.117(4) 0.087(3) -0.038(3) -0.001(3) 0.020(3) O6 0.059(8) 0.36(4) 0.29(3) -0.26(3) 0.056(12) -0.077(14) O6' 0.250(18) 0.240(18) 0.147(12) -0.098(12) -0.111(13) 0.137(16) C1 0.041(2) 0.054(3) 0.034(2) -0.0132(18) -0.0055(17) 0.004(2) C2 0.044(2) 0.058(3) 0.033(2) -0.0148(18) -0.0103(17) 0.008(2) C3 0.048(2) 0.049(3) 0.038(2) -0.0112(18) -0.0043(18) 0.003(2) C4 0.042(2) 0.047(3) 0.0312(19) -0.0124(17) -0.0039(16) 0.0039(19) C5 0.044(2) 0.053(3) 0.033(2) -0.0129(18) -0.0058(17) 0.007(2) C6 0.043(2) 0.056(3) 0.045(2) -0.026(2) -0.0051(19) 0.007(2) C7 0.042(2) 0.060(3) 0.044(2) -0.022(2) -0.0098(18) 0.003(2) C8 0.059(3) 0.067(3) 0.032(2) -0.015(2) 0.0011(19) -0.001(2) C9 0.045(2) 0.063(3) 0.046(2) -0.026(2) -0.0028(19) -0.001(2) C10 0.041(2) 0.055(3) 0.038(2) -0.0183(19) -0.0039(17) 0.006(2) C11 0.049(3) 0.079(4) 0.042(2) -0.026(2) -0.004(2) 0.004(3) C12 0.037(2) 0.059(3) 0.039(2) -0.0169(19) -0.0039(17) -0.004(2) C13 0.066(3) 0.062(3) 0.041(2) -0.007(2) 0.004(2) -0.007(3) C14 0.052(3) 0.066(4) 0.052(3) -0.015(2) 0.001(2) -0.011(2) C15 0.061(3) 0.054(3) 0.050(3) -0.015(2) 0.000(2) -0.010(2) C16 0.056(3) 0.076(4) 0.044(3) -0.014(2) 0.000(2) 0.002(3) C17 0.058(3) 0.081(4) 0.046(3) -0.033(2) -0.011(2) 0.005(3) C18 0.064(3) 0.068(4) 0.052(3) -0.021(2) -0.008(2) -0.009(3) C19 0.058(3) 0.085(4) 0.059(3) -0.041(3) -0.009(2) -0.006(3) C20 0.075(4) 0.073(4) 0.063(3) -0.032(3) -0.017(3) -0.003(3) C21 0.071(3) 0.065(4) 0.074(4) -0.026(3) -0.015(3) -0.014(3) O7 0.251(12) 0.200(10) 0.174(8) 0.067(8) -0.050(8) -0.046(9) O8 0.229(12) 0.301(17) 0.45(2) -0.251(17) -0.125(14) 0.133(13) O9 0.373(19) 0.259(15) 0.172(9) -0.048(9) 0.104(10) -0.058(13) _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 Cu1 O1 1.895(3) . ? Cu1 O2 1.920(3) . ? Cu1 N2 1.978(4) . ? Cu1 N1 1.999(4) . ? Cu1 O4 2.357(5) . ? N1 C9 1.329(6) . ? N1 C10 1.344(6) . ? N2 C6 1.335(6) . ? N2 C18 1.343(7) . ? N3 O7 1.108(8) . ? N3 O8 1.152(10) . ? N3 O9 1.202(10) . ? O1 C3 1.284(5) . ? O2 C1 1.251(5) . ? O3 C2 1.231(5) . ? O4 H4A 0.86(5) . ? O4 H4B 0.84(6) . ? O6 O6' 1.10(2) . ? C1 C4 1.440(6) . ? C1 C12 1.441(7) . ? C2 C5 1.465(7) . ? C2 C7 1.476(6) . ? C3 C4 1.415(7) . ? C3 C15 1.420(6) . ? C4 C5 1.426(6) . ? C5 C8 1.382(7) . ? C6 C17 1.394(6) . ? C6 C10 1.477(7) . ? C7 C12 1.335(6) . ? C7 C19 1.490(7) . ? C8 C13 1.365(8) . ? C8 H8 0.9300 . ? C9 C14 1.372(7) . ? C9 H9 0.9300 . ? C10 C11 1.372(7) . ? C11 C16 1.358(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C15 1.377(7) . ? C13 H13 0.9300 . ? C14 C16 1.375(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C20 1.369(8) . ? C17 H17 0.9300 . ? C18 C21 1.370(7) . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.392(8) . ? C20 H20 0.9300 . ? C21 H21 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 O1 Cu1 O2 91.63(15) . . ? O1 Cu1 N2 94.26(16) . . ? O2 Cu1 N2 172.42(15) . . ? O1 Cu1 N1 171.72(14) . . ? O2 Cu1 N1 92.66(16) . . ? N2 Cu1 N1 80.91(17) . . ? O1 Cu1 O4 96.26(16) . . ? O2 Cu1 O4 95.55(17) . . ? N2 Cu1 O4 88.55(18) . . ? N1 Cu1 O4 90.38(16) . . ? C9 N1 C10 118.6(4) . . ? C9 N1 Cu1 126.3(3) . . ? C10 N1 Cu1 115.1(3) . . ? C6 N2 C18 119.4(4) . . ? C6 N2 Cu1 115.1(3) . . ? C18 N2 Cu1 125.3(3) . . ? O7 N3 O8 125.7(12) . . ? O7 N3 O9 131.2(12) . . ? O8 N3 O9 100.3(11) . . ? C3 O1 Cu1 126.0(3) . . ? C1 O2 Cu1 127.3(3) . . ? Cu1 O4 H4A 115(5) . . ? Cu1 O4 H4B 119(5) . . ? H4A O4 H4B 111(7) . . ? O2 C1 C4 123.4(4) . . ? O2 C1 C12 117.0(4) . . ? C4 C1 C12 119.6(4) . . ? O3 C2 C5 121.4(4) . . ? O3 C2 C7 120.1(4) . . ? C5 C2 C7 118.4(4) . . ? O1 C3 C4 124.9(4) . . ? O1 C3 C15 117.7(4) . . ? C4 C3 C15 117.4(4) . . ? C3 C4 C5 119.8(4) . . ? C3 C4 C1 122.2(4) . . ? C5 C4 C1 118.0(4) . . ? C8 C5 C4 120.0(4) . . ? C8 C5 C2 119.2(4) . . ? C4 C5 C2 120.7(4) . . ? N2 C6 C17 121.5(5) . . ? N2 C6 C10 115.2(4) . . ? C17 C6 C10 123.2(4) . . ? C12 C7 C2 118.8(4) . . ? C12 C7 C19 123.6(4) . . ? C2 C7 C19 117.6(4) . . ? C13 C8 C5 120.1(4) . . ? C13 C8 H8 119.9 . . ? C5 C8 H8 119.9 . . ? N1 C9 C14 122.7(4) . . ? N1 C9 H9 118.7 . . ? C14 C9 H9 118.7 . . ? N1 C10 C11 121.3(5) . . ? N1 C10 C6 113.4(4) . . ? C11 C10 C6 125.2(4) . . ? C16 C11 C10 119.6(4) . . ? C16 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C7 C12 C1 123.9(4) . . ? C7 C12 H12 118.1 . . ? C1 C12 H12 118.1 . . ? C8 C13 C15 121.5(4) . . ? C8 C13 H13 119.3 . . ? C15 C13 H13 119.3 . . ? C9 C14 C16 118.3(5) . . ? C9 C14 H14 120.9 . . ? C16 C14 H14 120.9 . . ? C13 C15 C3 121.0(5) . . ? C13 C15 H15 119.5 . . ? C3 C15 H15 119.5 . . ? C11 C16 C14 119.5(5) . . ? C11 C16 H16 120.3 . . ? C14 C16 H16 120.3 . . ? C20 C17 C6 118.4(5) . . ? C20 C17 H17 120.8 . . ? C6 C17 H17 120.8 . . ? N2 C18 C21 122.4(5) . . ? N2 C18 H18 118.8 . . ? C21 C18 H18 118.8 . . ? C7 C19 H19A 109.5 . . ? C7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 C21 120.2(5) . . ? C17 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C18 C21 C20 118.0(6) . . ? C18 C21 H21 121.0 . . ? C20 C21 H21 121.0 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.015 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.103