# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 735402' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H11 Cu O7' _chemical_formula_weight 282.71 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 Tetragonal _symmetry_space_group_name_H-M P4/nmm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' 'y+1/2, x+1/2, -z' '-y, -x, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' '-y-1/2, -x-1/2, z' 'y, x, z' _cell_length_a 19.129(3) _cell_length_b 19.129(3) _cell_length_c 6.7640(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2475.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 654 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas None _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.780 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7558 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22829 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1569 _reflns_number_gt 1348 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0747P)^2^+2.7595P] 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 1569 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 0.531159(15) 0.531159(15) 0.14758(6) 0.0173(2) Uani 1 2 d S . . C1 C 0.52582(14) 0.31305(14) 0.2645(4) 0.0244(6) Uani 1 1 d . . . C2 C 0.54892(17) 0.31301(15) 0.4601(5) 0.0319(7) Uani 1 1 d . . . H2 H 0.5569 0.3551 0.5251 0.038 Uiso 1 1 calc R . . C3 C 0.5600(3) 0.2500 0.5581(7) 0.0385(11) Uani 1 2 d S . . H3 H 0.5749 0.2500 0.6890 0.046 Uiso 1 2 calc SR . . C4 C 0.5140(2) 0.2500 0.1676(6) 0.0256(8) Uani 1 2 d S . . H4 H 0.4981 0.2500 0.0376 0.031 Uiso 1 2 calc SR . . C5 C 0.51447(15) 0.38136(14) 0.1615(4) 0.0223(5) Uani 1 1 d . . . O1 O 0.48406(14) 0.38101(11) -0.0026(4) 0.0441(6) Uani 1 1 d . . . O2 O 0.53591(13) 0.43497(11) 0.2473(4) 0.0408(6) Uani 1 1 d . . . O1W O 0.57482(12) 0.57482(12) 0.4086(5) 0.0383(7) Uani 1 2 d S . . H1WA H 0.6048 0.6048 0.3949 0.046 Uiso 1 2 d SR . . H1WB H 0.5669 0.5669 0.5253 0.046 Uiso 1 2 d SR . . O2W O 0.6726(3) 0.6726(3) 0.9545(19) 0.241(6) Uani 1 2 d S . . H2WA H 0.6656 0.6656 1.0727 0.289 Uiso 1 2 d SR . . H2WB H 0.6480 0.6480 0.8832 0.289 Uiso 1 2 d SR . . O3W O 0.6721(3) 0.6721(3) 0.487(2) 0.300(9) Uani 1 2 d S . . H3WA H 0.7022 0.7022 0.5008 0.360 Uiso 1 2 d SR . . H3WB H 0.6580 0.6580 0.5943 0.360 Uiso 1 2 d SR . . 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 0.0159(2) 0.0159(2) 0.0200(3) -0.00074(11) -0.00074(11) -0.00081(14) C1 0.0302(14) 0.0174(12) 0.0256(14) 0.0015(10) -0.0026(11) -0.0007(10) C2 0.0456(16) 0.0194(12) 0.0308(16) -0.0024(11) -0.0071(13) -0.0014(12) C3 0.064(3) 0.024(2) 0.027(2) 0.000 -0.013(2) 0.000 C4 0.032(2) 0.0207(18) 0.0242(19) 0.000 -0.0023(16) 0.000 C5 0.0236(12) 0.0175(12) 0.0259(14) -0.0006(9) 0.0014(10) 0.0010(10) O1 0.0744(17) 0.0196(10) 0.0382(13) 0.0055(9) -0.0263(13) -0.0075(10) O2 0.0680(16) 0.0160(9) 0.0385(13) 0.0030(9) -0.0226(11) -0.0019(9) O1W 0.0440(11) 0.0440(11) 0.0271(15) -0.0072(10) -0.0072(10) -0.0051(15) O2W 0.209(9) 0.209(9) 0.305(14) 0.010(6) 0.010(6) -0.144(10) O3W 0.251(11) 0.251(11) 0.398(19) -0.040(7) -0.040(7) -0.187(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 Cu1 O2 1.962(2) 16 ? Cu1 O2 1.962(2) . ? Cu1 O1 1.967(2) 9_665 ? Cu1 O1 1.967(2) 8_665 ? Cu1 O1W 2.124(3) . ? Cu1 Cu1 2.6130(9) 9_665 ? C1 C4 1.391(3) . ? C1 C2 1.395(4) . ? C1 C5 1.497(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9300 . ? C3 C2 1.392(4) 13_565 ? C3 H3 0.9300 . ? C4 C1 1.391(3) 13_565 ? C4 H4 0.9300 . ? C5 O2 1.248(4) . ? C5 O1 1.253(4) . ? O1 Cu1 1.967(2) 9_665 ? O1W H1WA 0.8167 . ? O1W H1WB 0.8173 . ? O2W H2WA 0.8217 . ? O2W H2WB 0.8228 . ? O3W H3WA 0.8195 . ? O3W H3WB 0.8221 . ? 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 88.21(15) 16 . ? O2 Cu1 O1 89.60(12) 16 9_665 ? O2 Cu1 O1 168.34(9) . 9_665 ? O2 Cu1 O1 168.34(9) 16 8_665 ? O2 Cu1 O1 89.60(12) . 8_665 ? O1 Cu1 O1 90.25(18) 9_665 8_665 ? O2 Cu1 O1W 93.71(9) 16 . ? O2 Cu1 O1W 93.71(9) . . ? O1 Cu1 O1W 97.86(9) 9_665 . ? O1 Cu1 O1W 97.86(9) 8_665 . ? O2 Cu1 Cu1 81.72(7) 16 9_665 ? O2 Cu1 Cu1 81.72(7) . 9_665 ? O1 Cu1 Cu1 86.63(7) 9_665 9_665 ? O1 Cu1 Cu1 86.63(7) 8_665 9_665 ? O1W Cu1 Cu1 173.60(10) . 9_665 ? C4 C1 C2 119.9(3) . . ? C4 C1 C5 120.9(3) . . ? C2 C1 C5 119.2(2) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C2 120.0(4) 13_565 . ? C2 C3 H3 120.0 13_565 . ? C2 C3 H3 120.0 . . ? C1 C4 C1 120.2(4) . 13_565 ? C1 C4 H4 119.9 . . ? C1 C4 H4 119.9 13_565 . ? O2 C5 O1 124.7(3) . . ? O2 C5 C1 117.0(2) . . ? O1 C5 C1 118.4(2) . . ? C5 O1 Cu1 120.38(19) . 9_665 ? C5 O2 Cu1 126.57(19) . . ? Cu1 O1W H1WA 117.2 . . ? Cu1 O1W H1WB 131.0 . . ? H1WA O1W H1WB 111.7 . . ? H2WA O2W H2WB 112.5 . . ? H3WA O3W H3WB 111.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.821 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.114 data_2 _database_code_depnum_ccdc_archive 'CCDC 735403' #TrackingRef '- 100430 Crsytal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H9 Cu O5' _chemical_formula_weight 272.71 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 Tetragonal _symmetry_space_group_name_H-M P4/nmm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' 'y+1/2, x+1/2, -z' '-y, -x, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' '-y-1/2, -x-1/2, z' 'y, x, z' _cell_length_a 19.146(3) _cell_length_b 19.146(3) _cell_length_c 6.7427(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2471.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.768 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8769 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _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 ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18627 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.19 _reflns_number_total 1235 _reflns_number_gt 1046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku RAXIS-RAPID' _computing_cell_refinement 'Rigaku RAXIS-RAPID' _computing_data_reduction 'Rigaku RAXIS-RAPID' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1475P)^2^+32.2450P] 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 1235 _refine_ls_number_parameters 82 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0893 _refine_ls_wR_factor_ref 0.2704 _refine_ls_wR_factor_gt 0.2586 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.119 _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 Cu1 Cu 0.46912(4) 0.46912(4) 0.35198(18) 0.0187(6) Uani 1 2 d S . . C1 C 0.2500 0.5622(7) 1.0545(17) 0.037(3) Uani 1 2 d S . . H1 H 0.2500 0.5775 1.1854 0.044 Uiso 1 2 calc SR . . C2 C 0.3125(4) 0.5510(5) 0.9589(12) 0.0317(19) Uani 1 1 d . . . H2 H 0.3545 0.5593 1.0241 0.038 Uiso 1 1 calc R . . C3 C 0.3125(4) 0.5270(4) 0.7626(12) 0.0258(17) Uani 1 1 d . . . C4 C 0.2500 0.5143(6) 0.6660(17) 0.026(2) Uani 1 2 d S . . H4 H 0.2500 0.4974 0.5367 0.031 Uiso 1 2 calc SR . . C5 C 0.3817(4) 0.5149(4) 0.6606(11) 0.0245(17) Uani 1 1 d . . . C6 C 0.3769(4) 0.3769(4) 0.091(2) 0.051(4) Uani 1 2 d SD . . H6A H 0.3427 0.3992 0.1758 0.061 Uiso 0.50 1 calc PR . . H6B H 0.3992 0.3427 0.1758 0.061 Uiso 0.50 1 calc PR . . C7 C 0.3335(5) 0.3335(5) -0.019(2) 0.050(4) Uani 1 2 d SD . . H7A H 0.3056 0.3059 0.0699 0.060 Uiso 1 2 calc SR . . H7B H 0.3613 0.3033 -0.1002 0.060 Uiso 0.50 1 calc PR . . H7C H 0.3036 0.3613 -0.1012 0.060 Uiso 0.50 1 calc PR . . O1 O 0.4346(3) 0.5358(4) 0.7482(10) 0.0417(17) Uani 1 1 d . . . O2 O 0.3816(3) 0.4847(4) 0.4965(10) 0.0466(18) Uani 1 1 d . . . O3 O 0.4250(3) 0.4250(3) 0.0889(12) 0.038(2) Uani 1 2 d SD . . 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 0.0173(6) 0.0173(6) 0.0214(9) -0.0005(3) -0.0005(3) -0.0004(4) C1 0.030(6) 0.057(8) 0.023(6) -0.013(6) 0.000 0.000 C2 0.018(4) 0.046(5) 0.031(5) -0.005(4) -0.003(3) -0.002(3) C3 0.017(4) 0.032(4) 0.028(4) -0.003(3) 0.002(3) 0.001(3) C4 0.022(5) 0.031(6) 0.026(6) 0.001(5) 0.000 0.000 C5 0.019(4) 0.025(4) 0.029(4) 0.001(3) 0.002(3) 0.002(3) C6 0.051(5) 0.051(5) 0.051(9) 0.000(5) 0.000(5) 0.000(7) C7 0.050(5) 0.050(5) 0.051(9) 0.000(5) 0.000(5) 0.000(6) O1 0.016(3) 0.070(4) 0.039(4) -0.023(3) 0.002(3) -0.002(3) O2 0.022(3) 0.079(5) 0.038(4) -0.029(4) 0.006(3) -0.007(3) O3 0.043(3) 0.043(3) 0.028(4) -0.006(3) -0.006(3) -0.007(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 Cu1 O2 1.961(6) . ? Cu1 O2 1.961(6) 16 ? Cu1 O1 1.966(6) 8_666 ? Cu1 O1 1.966(6) 9_666 ? Cu1 O3 2.139(8) . ? Cu1 Cu1 2.604(2) 9_666 ? C1 C2 1.376(10) 14_655 ? C1 C2 1.376(10) . ? C1 H1 0.9300 . ? C2 C3 1.401(12) . ? C2 H2 0.9300 . ? C3 C4 1.384(10) . ? C3 C5 1.511(10) . ? C4 C3 1.384(10) 14_655 ? C4 H4 0.9300 . ? C5 O1 1.240(10) . ? C5 O2 1.248(10) . ? C6 O3 1.303(9) . ? C6 C7 1.387(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O1 Cu1 1.966(6) 9_666 ? 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 90.8(5) . 16 ? O2 Cu1 O1 89.2(3) . 8_666 ? O2 Cu1 O1 168.4(3) 16 8_666 ? O2 Cu1 O1 168.4(3) . 9_666 ? O2 Cu1 O1 89.2(3) 16 9_666 ? O1 Cu1 O1 88.4(4) 8_666 9_666 ? O2 Cu1 O3 97.8(2) . . ? O2 Cu1 O3 97.8(2) 16 . ? O1 Cu1 O3 93.8(2) 8_666 . ? O1 Cu1 O3 93.8(2) 9_666 . ? O2 Cu1 Cu1 86.44(19) . 9_666 ? O2 Cu1 Cu1 86.44(19) 16 9_666 ? O1 Cu1 Cu1 81.93(18) 8_666 9_666 ? O1 Cu1 Cu1 81.93(18) 9_666 9_666 ? O3 Cu1 Cu1 174.0(2) . 9_666 ? C2 C1 C2 120.9(11) 14_655 . ? C2 C1 H1 119.6 14_655 . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.5(8) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.2(7) . . ? C4 C3 C5 121.1(7) . . ? C2 C3 C5 118.7(7) . . ? C3 C4 C3 119.7(10) . 14_655 ? C3 C4 H4 120.2 . . ? C3 C4 H4 120.2 14_655 . ? O1 C5 O2 125.0(7) . . ? O1 C5 C3 116.8(7) . . ? O2 C5 C3 118.3(7) . . ? O3 C6 C7 147.4(14) . . ? O3 C6 H6A 99.9 . . ? C7 C6 H6A 99.9 . . ? O3 C6 H6B 99.9 . . ? C7 C6 H6B 99.9 . . ? H6A C6 H6B 104.2 . . ? 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 . . ? C5 O1 Cu1 126.0(5) . 9_666 ? C5 O2 Cu1 120.7(5) . . ? C6 O3 Cu1 123.4(8) . . ? 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 C2 C1 C2 C3 -0.9(19) 14_655 . . . ? C1 C2 C3 C4 -0.3(14) . . . . ? C1 C2 C3 C5 -179.8(9) . . . . ? C2 C3 C4 C3 1.5(16) . . . 14_655 ? C5 C3 C4 C3 -179.0(7) . . . 14_655 ? C4 C3 C5 O1 171.1(9) . . . . ? C2 C3 C5 O1 -9.4(12) . . . . ? C4 C3 C5 O2 -9.1(13) . . . . ? C2 C3 C5 O2 170.4(8) . . . . ? O2 C5 O1 Cu1 2.8(13) . . . 9_666 ? C3 C5 O1 Cu1 -177.4(5) . . . 9_666 ? O1 C5 O2 Cu1 -1.7(13) . . . . ? C3 C5 O2 Cu1 178.5(6) . . . . ? O2 Cu1 O2 C5 86.5(7) 16 . . . ? O1 Cu1 O2 C5 -81.8(7) 8_666 . . . ? O1 Cu1 O2 C5 -3(2) 9_666 . . . ? O3 Cu1 O2 C5 -175.6(7) . . . . ? Cu1 Cu1 O2 C5 0.1(7) 9_666 . . . ? C7 C6 O3 Cu1 180.000(3) . . . . ? O2 Cu1 O3 C6 -45.9(2) . . . . ? O2 Cu1 O3 C6 45.9(2) 16 . . . ? O1 Cu1 O3 C6 -135.7(2) 8_666 . . . ? O1 Cu1 O3 C6 135.7(2) 9_666 . . . ? Cu1 Cu1 O3 C6 180.000(14) 9_666 . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.753 _refine_diff_density_min -4.201 _refine_diff_density_rms 0.232 data_3 _database_code_depnum_ccdc_archive 'CCDC 735404' #TrackingRef '- 100430 Crsytal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 Cu2 N O10' _chemical_formula_weight 574.49 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' Cu Cu 0.3201 1.2651 '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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 18.0520(4) _cell_length_b 13.8360(3) _cell_length_c 19.1140(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4774.06(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1450 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 1.836 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8645 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _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 ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31217 _diffrn_reflns_av_R_equivalents 0.1265 _diffrn_reflns_av_sigmaI/netI 0.1622 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.20 _reflns_number_total 4299 _reflns_number_gt 1968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku RAXIS-RAPID' _computing_cell_refinement 'Rigaku RAXIS-RAPID' _computing_data_reduction 'Rigaku RAXIS-RAPID' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1615P)^2^+75.3646P] 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 4299 _refine_ls_number_parameters 287 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.2341 _refine_ls_R_factor_gt 0.1322 _refine_ls_wR_factor_ref 0.3843 _refine_ls_wR_factor_gt 0.3095 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.022 _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 0.23193(12) 0.16765(15) 0.51182(11) 0.0494(7) Uani 1 1 d . . . Cu2 Cu 0.30899(11) 0.30896(14) 0.45728(11) 0.0488(7) Uani 1 1 d . . . C1 C 0.2594(9) 0.1174(13) 0.2948(9) 0.051(4) Uani 1 1 d . . . C2 C 0.2684(9) 0.1657(12) 0.2343(9) 0.049(4) Uani 1 1 d . . . H2 H 0.2819 0.2305 0.2363 0.058 Uiso 1 1 calc R . . C3 C 0.2585(9) 0.1242(13) 0.1696(9) 0.052(4) Uani 1 1 d . . . C4 C 0.2398(11) 0.0253(13) 0.1668(10) 0.061(5) Uani 1 1 d . . . H4 H 0.2343 -0.0060 0.1240 0.073 Uiso 1 1 calc R . . C5 C 0.2301(12) -0.0234(14) 0.2280(9) 0.070(6) Uani 1 1 d . . . H5 H 0.2163 -0.0882 0.2265 0.083 Uiso 1 1 calc R . . C6 C 0.2400(10) 0.0195(13) 0.2909(9) 0.057(5) Uani 1 1 d . . . H6 H 0.2339 -0.0161 0.3318 0.069 Uiso 1 1 calc R . . C7 C 0.2692(9) 0.1626(12) 0.3640(9) 0.049(4) Uani 1 1 d . . . C8 C 0.2639(9) 0.1780(13) 0.1031(8) 0.049(4) Uani 1 1 d . . . C9 C 0.4529(9) 0.1063(12) 0.5531(9) 0.051(4) Uani 1 1 d . . . C10 C 0.5197(9) 0.1543(12) 0.5416(9) 0.050(4) Uani 1 1 d . . . H10 H 0.5189 0.2132 0.5181 0.060 Uiso 1 1 calc R . . C11 C 0.5872(9) 0.1177(12) 0.5637(9) 0.051(4) Uani 1 1 d . . . C12 C 0.5871(9) 0.0303(14) 0.5993(10) 0.060(5) Uani 1 1 d . . . H12 H 0.6316 0.0035 0.6142 0.072 Uiso 1 1 calc R . . C13 C 0.5209(9) -0.0172(13) 0.6128(10) 0.060(5) Uani 1 1 d . . . H13 H 0.5211 -0.0747 0.6380 0.072 Uiso 1 1 calc R . . C14 C 0.4550(9) 0.0206(13) 0.5890(10) 0.062(5) Uani 1 1 d . . . H14 H 0.4111 -0.0126 0.5975 0.074 Uiso 1 1 calc R . . C15 C 0.3850(10) 0.1481(12) 0.5254(9) 0.050(4) Uani 1 1 d . . . C16 C 0.6574(10) 0.1670(12) 0.5483(8) 0.047(4) Uani 1 1 d . . . C17 C 0.4393(13) 0.3828(17) 0.3919(13) 0.096(8) Uani 1 1 d D . . C18 C 0.5611(8) 0.3834(10) 0.3257(8) 0.050(4) Uiso 1 1 d D . . C19 C 0.5505(9) 0.3146(11) 0.2718(8) 0.050(4) Uiso 1 1 d D . . C20 C 0.4685(9) 0.5251(9) 0.3315(8) 0.050(4) Uiso 1 1 d D . . C21 C 0.5041(9) 0.5956(11) 0.3744(8) 0.050(4) Uiso 1 1 d D . . N1 N 0.4950(9) 0.4306(12) 0.3529(12) 0.116(7) Uani 1 1 d D . . O1 O 0.2366(6) 0.1236(8) 0.4153(6) 0.054(3) Uani 1 1 d . . . O2 O 0.3088(6) 0.2389(8) 0.3683(6) 0.053(3) Uani 1 1 d . . . O3 O 0.2402(7) 0.2657(9) 0.1017(6) 0.060(3) Uani 1 1 d . . . O4 O 0.2938(6) 0.1366(8) 0.0512(6) 0.055(3) Uani 1 1 d . . . O5 O 0.3253(6) 0.1029(9) 0.5342(6) 0.059(3) Uani 1 1 d . . . O6 O 0.3891(6) 0.2287(8) 0.4951(6) 0.053(3) Uani 1 1 d . . . O7 O 0.6514(6) 0.2446(9) 0.5132(7) 0.062(3) Uani 1 1 d . . . O8 O 0.7164(6) 0.1338(9) 0.5705(7) 0.057(3) Uani 1 1 d . . . O9 O 0.3869(7) 0.4165(9) 0.4203(7) 0.068(4) Uani 1 1 d . . . O1W O 0.1549(6) 0.0507(8) 0.5309(6) 0.062(3) Uani 1 1 d . . . H1WA H 0.1311 0.0360 0.4959 0.075 Uiso 1 1 d R . . H1WB H 0.1675 0.0026 0.5527 0.075 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 Cu1 0.0499(12) 0.0551(12) 0.0432(12) 0.0016(10) 0.0004(9) -0.0006(10) Cu2 0.0503(12) 0.0557(12) 0.0404(12) 0.0014(9) 0.0005(10) -0.0008(10) C1 0.050(10) 0.064(11) 0.038(10) 0.007(8) -0.005(8) 0.002(9) C2 0.050(10) 0.044(9) 0.052(11) -0.009(8) -0.001(8) 0.000(8) C3 0.052(10) 0.068(11) 0.037(10) -0.002(8) -0.009(8) 0.005(9) C4 0.076(13) 0.064(12) 0.043(11) -0.006(9) 0.008(10) 0.000(10) C5 0.105(16) 0.061(12) 0.043(11) -0.005(9) 0.004(11) -0.026(11) C6 0.076(12) 0.064(12) 0.033(10) 0.003(8) 0.002(9) -0.002(10) C7 0.049(10) 0.057(10) 0.043(10) 0.001(8) 0.007(8) 0.010(9) C8 0.048(9) 0.063(11) 0.036(10) -0.008(8) -0.007(8) -0.012(9) C9 0.045(9) 0.056(10) 0.051(11) -0.002(9) 0.005(8) -0.001(9) C10 0.053(10) 0.053(10) 0.043(10) 0.004(8) -0.001(8) 0.004(8) C11 0.050(10) 0.055(10) 0.047(11) -0.001(8) 0.003(8) -0.005(9) C12 0.033(9) 0.076(13) 0.071(14) -0.005(11) -0.006(8) 0.000(9) C13 0.046(10) 0.058(11) 0.077(14) 0.017(10) 0.006(9) 0.006(9) C14 0.035(9) 0.068(12) 0.081(15) 0.008(11) 0.001(9) 0.005(9) C15 0.051(10) 0.050(10) 0.049(11) 0.006(8) -0.001(8) 0.004(9) C16 0.053(10) 0.062(11) 0.026(9) 0.005(8) 0.007(8) -0.005(9) C17 0.085(17) 0.085(16) 0.12(2) 0.007(15) 0.019(16) -0.012(15) N1 0.082(13) 0.106(17) 0.16(2) 0.010(16) 0.005(14) -0.004(13) O1 0.068(7) 0.055(7) 0.040(7) -0.005(5) 0.002(6) -0.005(6) O2 0.057(7) 0.058(7) 0.045(7) 0.003(5) 0.001(6) -0.013(6) O3 0.072(8) 0.068(8) 0.039(7) 0.002(6) -0.005(6) 0.008(7) O4 0.070(8) 0.057(7) 0.038(7) 0.003(5) 0.004(6) 0.003(6) O5 0.053(7) 0.066(8) 0.057(8) 0.020(6) -0.008(6) 0.000(6) O6 0.041(6) 0.067(8) 0.051(7) 0.012(6) -0.007(5) 0.001(6) O7 0.050(7) 0.069(8) 0.067(9) 0.008(7) -0.002(6) -0.002(6) O8 0.043(7) 0.061(7) 0.068(9) 0.010(6) -0.006(6) 0.004(6) O9 0.054(8) 0.069(8) 0.082(10) 0.001(7) 0.014(7) -0.002(7) O1W 0.065(7) 0.055(7) 0.066(9) 0.007(6) 0.005(6) -0.008(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.945(11) . ? Cu1 O7 1.953(12) 3_456 ? Cu1 O3 1.955(11) 8_566 ? Cu1 O5 1.956(11) . ? Cu1 O1W 2.165(11) . ? Cu1 Cu2 2.616(3) . ? Cu2 O8 1.923(11) 3_456 ? Cu2 O2 1.958(11) . ? Cu2 O6 1.962(11) . ? Cu2 O4 1.966(11) 8_566 ? Cu2 O9 2.166(13) . ? C1 C2 1.35(2) . ? C1 C6 1.40(2) . ? C1 C7 1.47(2) . ? C2 C3 1.37(2) . ? C2 H2 0.9300 . ? C3 C4 1.41(2) . ? C3 C8 1.48(2) . ? C4 C5 1.36(2) . ? C4 H4 0.9300 . ? C5 C6 1.35(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.264(19) . ? C7 O2 1.279(19) . ? C8 O4 1.266(19) . ? C8 O3 1.29(2) . ? C9 C14 1.37(2) . ? C9 C10 1.39(2) . ? C9 C15 1.46(2) . ? C10 C11 1.39(2) . ? C10 H10 0.9300 . ? C11 C12 1.39(2) . ? C11 C16 1.47(2) . ? C12 C13 1.39(2) . ? C12 H12 0.9300 . ? C13 C14 1.38(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O5 1.256(19) . ? C15 O6 1.259(19) . ? C16 O8 1.236(19) . ? C16 O7 1.270(19) . ? C17 O9 1.19(2) . ? C17 N1 1.417(10) . ? C18 C19 1.416(9) . ? C18 N1 1.455(9) . ? C20 C21 1.427(9) . ? C20 N1 1.451(10) . ? O3 Cu1 1.955(11) 8_565 ? O4 Cu2 1.966(11) 8_565 ? O7 Cu1 1.953(12) 3_556 ? O8 Cu2 1.923(11) 3_556 ? O1W H1WA 0.8207 . ? O1W H1WB 0.8172 . ? 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 O7 89.7(5) . 3_456 ? O1 Cu1 O3 167.9(5) . 8_566 ? O7 Cu1 O3 88.8(5) 3_456 8_566 ? O1 Cu1 O5 91.5(5) . . ? O7 Cu1 O5 168.3(5) 3_456 . ? O3 Cu1 O5 87.6(5) 8_566 . ? O1 Cu1 O1W 87.4(5) . . ? O7 Cu1 O1W 91.6(5) 3_456 . ? O3 Cu1 O1W 104.7(5) 8_566 . ? O5 Cu1 O1W 100.1(5) . . ? O1 Cu1 Cu2 80.4(3) . . ? O7 Cu1 Cu2 80.4(4) 3_456 . ? O3 Cu1 Cu2 87.5(4) 8_566 . ? O5 Cu1 Cu2 88.3(4) . . ? O1W Cu1 Cu2 165.3(3) . . ? O8 Cu2 O2 87.9(5) 3_456 . ? O8 Cu2 O6 167.2(5) 3_456 . ? O2 Cu2 O6 92.3(5) . . ? O8 Cu2 O4 88.4(5) 3_456 8_566 ? O2 Cu2 O4 169.3(5) . 8_566 ? O6 Cu2 O4 89.1(5) . 8_566 ? O8 Cu2 O9 101.0(5) 3_456 . ? O2 Cu2 O9 93.3(5) . . ? O6 Cu2 O9 91.7(5) . . ? O4 Cu2 O9 97.2(5) 8_566 . ? O8 Cu2 Cu1 87.5(4) 3_456 . ? O2 Cu2 Cu1 88.6(3) . . ? O6 Cu2 Cu1 79.8(3) . . ? O4 Cu2 Cu1 81.3(3) 8_566 . ? O9 Cu2 Cu1 171.4(4) . . ? C2 C1 C6 117.8(16) . . ? C2 C1 C7 123.1(16) . . ? C6 C1 C7 119.1(15) . . ? C1 C2 C3 123.3(17) . . ? C1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C2 C3 C4 118.1(16) . . ? C2 C3 C8 123.8(16) . . ? C4 C3 C8 118.1(15) . . ? C5 C4 C3 118.6(17) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C6 C5 C4 122.0(18) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C1 120.2(17) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 O2 124.2(15) . . ? O1 C7 C1 117.4(16) . . ? O2 C7 C1 118.4(15) . . ? O4 C8 O3 123.4(16) . . ? O4 C8 C3 118.4(16) . . ? O3 C8 C3 118.1(15) . . ? C14 C9 C10 117.9(16) . . ? C14 C9 C15 123.3(16) . . ? C10 C9 C15 118.8(15) . . ? C11 C10 C9 122.6(16) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 117.8(15) . . ? C10 C11 C16 121.9(16) . . ? C12 C11 C16 120.3(16) . . ? C11 C12 C13 120.4(16) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.1(17) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C9 C14 C13 121.2(17) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? O5 C15 O6 123.6(15) . . ? O5 C15 C9 118.4(15) . . ? O6 C15 C9 118.0(16) . . ? O8 C16 O7 124.7(15) . . ? O8 C16 C11 120.2(15) . . ? O7 C16 C11 115.1(16) . . ? O9 C17 N1 129(2) . . ? C19 C18 N1 116.7(16) . . ? C21 C20 N1 107.8(15) . . ? C17 N1 C20 109.6(15) . . ? C17 N1 C18 124.1(17) . . ? C20 N1 C18 125.0(15) . . ? C7 O1 Cu1 128.5(11) . . ? C7 O2 Cu2 117.8(10) . . ? C8 O3 Cu1 119.3(11) . 8_565 ? C8 O4 Cu2 127.0(11) . 8_565 ? C15 O5 Cu1 118.8(10) . . ? C15 O6 Cu2 128.8(11) . . ? C16 O7 Cu1 126.2(11) . 3_556 ? C16 O8 Cu2 120.1(11) . 3_556 ? C17 O9 Cu2 113.4(13) . . ? Cu1 O1W H1WA 112.6 . . ? Cu1 O1W H1WB 121.0 . . ? H1WA O1W H1WB 111.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.289 _refine_diff_density_min -2.371 _refine_diff_density_rms 0.180 data_4 _database_code_depnum_ccdc_archive 'CCDC 735405' #TrackingRef '- 100430 Crsytal data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Cu2 N2 O11' _chemical_formula_weight 634.55 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 Orthorhombic _symmetry_space_group_name_H-M Cmca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 28.339(6) _cell_length_b 25.097(5) _cell_length_c 15.483(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 11012(4) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2798 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5200 _exptl_absorpt_coefficient_mu 1.604 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7421 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _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 ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28822 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.20 _reflns_number_total 4590 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku RAXIS-RAPID' _computing_cell_refinement 'Rigaku RAXIS-RAPID' _computing_data_reduction 'Rigaku RAXIS-RAPID' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1558P)^2^+74.4621P] 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 4590 _refine_ls_number_parameters 346 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2626 _refine_ls_wR_factor_gt 0.2313 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 Cu1 Cu 0.28042(3) 1.09796(3) 0.18542(7) 0.0330(3) Uani 1 1 d . . . Cu2 Cu 0.0000 0.88449(5) 0.31930(9) 0.0283(4) Uani 1 2 d S . . Cu3 Cu 0.0000 0.80900(4) 0.19969(9) 0.0280(4) Uani 1 2 d S . . C1 C 0.1096(2) 0.9179(3) 0.1409(6) 0.040(2) Uani 1 1 d . . . C2 C 0.1325(2) 0.9609(3) 0.1767(6) 0.0357(18) Uani 1 1 d . . . H2 H 0.1197 0.9780 0.2245 0.043 Uiso 1 1 calc R . . C3 C 0.1747(2) 0.9788(3) 0.1416(6) 0.0361(18) Uani 1 1 d . . . C4 C 0.1938(3) 0.9524(3) 0.0720(6) 0.048(2) Uani 1 1 d . . . H4 H 0.2226 0.9634 0.0495 0.058 Uiso 1 1 calc R . . C5 C 0.1705(4) 0.9096(4) 0.0353(8) 0.066(3) Uani 1 1 d . . . H5 H 0.1831 0.8928 -0.0130 0.079 Uiso 1 1 calc R . . C6 C 0.1287(3) 0.8918(4) 0.0698(7) 0.059(3) Uani 1 1 d . . . H6 H 0.1133 0.8625 0.0459 0.071 Uiso 1 1 calc R . . C7 C 0.0655(3) 0.8952(3) 0.1839(6) 0.039(2) Uani 1 1 d . . . C8 C 0.2007(3) 1.0251(3) 0.1827(6) 0.040(2) Uani 1 1 d . . . C9 C 0.1082(3) 0.7730(3) 0.3780(6) 0.040(2) Uani 1 1 d . . . C10 C 0.1341(2) 0.7336(3) 0.3337(6) 0.0382(19) Uani 1 1 d . . . H10 H 0.1247 0.7227 0.2789 0.046 Uiso 1 1 calc R . . C11 C 0.1738(3) 0.7111(3) 0.3721(7) 0.047(2) Uani 1 1 d . . . C12 C 0.1873(3) 0.7274(3) 0.4537(8) 0.064(3) Uani 1 1 d . . . H12 H 0.2138 0.7122 0.4793 0.077 Uiso 1 1 calc R . . C13 C 0.1623(4) 0.7657(4) 0.4976(8) 0.070(3) Uani 1 1 d . . . H13 H 0.1720 0.7767 0.5522 0.084 Uiso 1 1 calc R . . C14 C 0.1219(3) 0.7882(3) 0.4591(6) 0.055(3) Uani 1 1 d . . . H14 H 0.1044 0.8135 0.4891 0.065 Uiso 1 1 calc R . . C15 C 0.0656(3) 0.7972(3) 0.3352(6) 0.0367(18) Uani 1 1 d . . . C16 C 0.2024(3) 0.6697(3) 0.3242(7) 0.044(2) Uani 1 1 d . . . C17 C 0.3050(3) 1.1046(4) 0.0009(8) 0.056(3) Uani 1 1 d . . . C18 C 0.3646(5) 1.0573(5) -0.0816(9) 0.088(4) Uani 1 1 d . . . C19 C 0.3022(7) 1.1077(8) -0.1547(12) 0.124(6) Uani 1 1 d . . . C20 C 0.0632(11) 0.0550(8) 0.3244(13) 0.180(13) Uani 1 1 d . . . C21 C 0.0566(9) 0.1501(7) 0.3520(18) 0.196(11) Uani 1 1 d . . . C22 C 0.0712(6) 0.0980(7) 0.1974(18) 0.137(9) Uani 1 1 d . . . N1 N 0.3224(3) 1.0910(3) -0.0762(7) 0.063(2) Uani 1 1 d . . . N2 N 0.0627(4) 0.0975(4) 0.2883(12) 0.097(4) Uani 1 1 d . . . O1 O 0.0485(2) 0.8541(2) 0.1501(4) 0.0490(16) Uani 1 1 d . . . O2 O 0.04944(17) 0.9189(2) 0.2482(4) 0.0427(14) Uani 1 1 d . . . O3 O 0.23767(18) 1.0404(2) 0.1440(4) 0.0452(15) Uani 1 1 d . . . O4 O 0.18422(17) 1.0443(2) 0.2500(4) 0.0442(14) Uani 1 1 d . . . O5 O 0.04943(18) 0.7747(2) 0.2697(4) 0.0436(15) Uani 1 1 d . . . O6 O 0.04980(19) 0.8393(2) 0.3687(4) 0.0433(14) Uani 1 1 d . . . O7 O 0.1877(2) 0.6553(2) 0.2519(5) 0.0513(18) Uani 1 1 d . . . O8 O 0.23725(18) 0.6512(2) 0.3633(4) 0.0466(16) Uani 1 1 d . . . O9 O 0.3217(2) 1.0926(2) 0.0710(5) 0.0510(16) Uani 1 1 d . . . O10 O 0.0430(6) 0.0394(6) 0.4049(17) 0.224(9) Uani 1 1 d . . . O11 O 0.0000 0.7535(3) 0.0986(6) 0.050(2) Uiso 1 2 d SD . . O1W O 0.0000 0.9420(3) 0.4214(6) 0.056(2) Uani 1 2 d S . . H1WA H 0.0000 0.9747 0.4267 0.085 Uiso 1 2 d SR . . H1WB H 0.0000 0.9277 0.4692 0.085 Uiso 1 2 d SR . . C23 C 0.0000 0.8029(6) -0.0387(13) 0.106(7) Uani 1 2 d SD . . C24 C 0.0000 0.7570(5) 0.0129(7) 0.050(3) Uiso 1 2 d SD . . 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 0.0200(5) 0.0291(6) 0.0498(8) -0.0015(4) 0.0095(4) -0.0002(3) Cu2 0.0255(6) 0.0242(7) 0.0351(9) -0.0038(5) 0.000 0.000 Cu3 0.0208(6) 0.0267(7) 0.0365(9) -0.0042(5) 0.000 0.000 C1 0.020(3) 0.043(4) 0.056(6) 0.010(4) 0.002(3) -0.010(3) C2 0.030(4) 0.039(4) 0.038(6) 0.006(3) -0.007(3) -0.002(3) C3 0.026(4) 0.034(4) 0.048(6) 0.005(3) 0.000(3) -0.009(3) C4 0.041(5) 0.050(5) 0.054(7) 0.000(4) 0.013(4) -0.016(4) C5 0.063(6) 0.071(7) 0.064(9) -0.011(5) 0.018(5) -0.025(5) C6 0.056(6) 0.060(6) 0.061(8) -0.009(5) 0.015(5) -0.025(4) C7 0.028(4) 0.042(4) 0.047(6) 0.014(4) -0.002(3) -0.002(3) C8 0.024(4) 0.033(4) 0.064(7) 0.006(4) -0.004(4) 0.001(3) C9 0.037(4) 0.031(4) 0.051(6) 0.001(4) -0.009(4) 0.009(3) C10 0.031(4) 0.037(4) 0.046(6) -0.003(3) -0.007(3) 0.004(3) C11 0.032(4) 0.033(4) 0.076(8) -0.005(4) -0.017(4) 0.002(3) C12 0.058(6) 0.044(5) 0.090(9) -0.014(5) -0.038(6) 0.015(4) C13 0.079(7) 0.058(6) 0.072(9) -0.029(5) -0.040(6) 0.027(5) C14 0.074(6) 0.044(5) 0.045(7) -0.017(4) -0.019(5) 0.023(4) C15 0.031(4) 0.035(4) 0.044(6) 0.003(4) -0.005(3) 0.001(3) C16 0.033(4) 0.026(4) 0.073(8) -0.004(4) -0.015(4) -0.002(3) C17 0.047(5) 0.057(6) 0.063(9) -0.005(5) 0.022(5) 0.001(4) C18 0.105(9) 0.074(7) 0.084(11) 0.004(6) 0.048(7) 0.027(6) C19 0.139(15) 0.182(17) 0.052(13) -0.001(10) 0.023(9) 0.034(12) C20 0.35(4) 0.113(14) 0.074(16) 0.038(11) 0.072(17) 0.129(18) C21 0.23(2) 0.093(12) 0.27(3) 0.020(15) -0.01(2) -0.111(15) C22 0.082(12) 0.117(14) 0.21(3) 0.057(14) -0.013(13) 0.005(8) N1 0.064(5) 0.067(5) 0.056(7) -0.009(4) 0.021(4) -0.003(4) N2 0.046(5) 0.075(7) 0.169(15) -0.027(8) 0.004(7) -0.001(4) O1 0.045(3) 0.052(4) 0.050(5) -0.005(3) 0.003(3) -0.025(3) O2 0.028(3) 0.039(3) 0.061(5) 0.000(3) 0.006(3) -0.008(2) O3 0.032(3) 0.045(3) 0.059(5) 0.000(3) 0.007(3) -0.013(2) O4 0.025(3) 0.047(3) 0.061(5) -0.002(3) 0.006(3) -0.010(2) O5 0.035(3) 0.043(3) 0.053(4) -0.010(3) -0.013(3) 0.013(2) O6 0.051(3) 0.036(3) 0.043(4) -0.007(3) -0.008(3) 0.017(2) O7 0.039(3) 0.037(3) 0.078(6) -0.010(3) -0.015(3) 0.011(2) O8 0.032(3) 0.043(3) 0.066(5) 0.001(3) -0.015(3) 0.011(2) O9 0.040(3) 0.064(4) 0.049(5) -0.001(3) 0.018(3) 0.003(3) O10 0.172(14) 0.127(11) 0.37(3) -0.066(15) -0.029(17) -0.010(9) O1W 0.084(7) 0.044(5) 0.041(7) -0.013(4) 0.000 0.000 C23 0.17(2) 0.077(12) 0.075(17) 0.005(10) 0.000 0.000 _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 O4 1.953(6) 7_545 ? Cu1 O8 1.963(6) 10_566 ? Cu1 O7 1.988(6) 16 ? Cu1 O3 1.991(5) . ? Cu1 O9 2.127(7) . ? Cu1 Cu1 2.6404(18) 7_545 ? Cu2 O6 1.966(5) 12 ? Cu2 O6 1.966(5) . ? Cu2 O2 1.980(5) . ? Cu2 O2 1.980(5) 12 ? Cu2 O1W 2.141(8) . ? Cu2 Cu3 2.6494(18) . ? Cu3 O1 1.940(5) 12 ? Cu3 O1 1.940(5) . ? Cu3 O5 1.969(5) 12 ? Cu3 O5 1.969(5) . ? Cu3 O11 2.094(9) . ? C1 C2 1.375(11) . ? C1 C6 1.391(13) . ? C1 C7 1.527(10) . ? C2 C3 1.387(10) . ? C2 H2 0.9300 . ? C3 C4 1.377(12) . ? C3 C8 1.515(11) . ? C4 C5 1.384(12) . ? C4 H4 0.9300 . ? C5 C6 1.375(13) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O2 1.245(11) . ? C7 O1 1.253(10) . ? C8 O4 1.240(10) . ? C8 O3 1.266(10) . ? C9 C14 1.368(12) . ? C9 C10 1.409(11) . ? C9 C15 1.505(10) . ? C10 C11 1.393(10) . ? C10 H10 0.9300 . ? C11 C12 1.383(14) . ? C11 C16 1.512(12) . ? C12 C13 1.373(13) . ? C12 H12 0.9300 . ? C13 C14 1.410(12) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O5 1.248(10) . ? C15 O6 1.259(9) . ? C16 O7 1.247(10) . ? C16 O8 1.248(10) . ? C17 O9 1.223(13) . ? C17 N1 1.336(14) . ? C18 N1 1.467(14) . ? C19 N1 1.41(2) . ? C20 N2 1.20(2) . ? C20 O10 1.43(3) . ? C21 N2 1.66(3) . ? C22 N2 1.43(3) . ? O4 Cu1 1.953(6) 7_545 ? O7 Cu1 1.988(6) 16_545 ? O8 Cu1 1.963(6) 10_556 ? O11 C24 1.331(9) . ? O1W H1WA 0.8244 . ? O1W H1WB 0.8227 . ? C23 C24 1.402(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O8 170.3(3) 7_545 10_566 ? O4 Cu1 O7 90.0(3) 7_545 16 ? O8 Cu1 O7 89.4(3) 10_566 16 ? O4 Cu1 O3 88.7(2) 7_545 . ? O8 Cu1 O3 89.5(3) 10_566 . ? O7 Cu1 O3 165.7(3) 16 . ? O4 Cu1 O9 95.8(3) 7_545 . ? O8 Cu1 O9 93.8(3) 10_566 . ? O7 Cu1 O9 103.1(3) 16 . ? O3 Cu1 O9 91.2(2) . . ? O4 Cu1 Cu1 86.97(18) 7_545 7_545 ? O8 Cu1 Cu1 83.36(18) 10_566 7_545 ? O7 Cu1 Cu1 84.54(18) 16 7_545 ? O3 Cu1 Cu1 81.16(17) . 7_545 ? O9 Cu1 Cu1 171.83(19) . 7_545 ? O6 Cu2 O6 91.8(4) 12 . ? O6 Cu2 O2 167.4(3) 12 . ? O6 Cu2 O2 87.7(2) . . ? O6 Cu2 O2 87.7(2) 12 12 ? O6 Cu2 O2 167.4(3) . 12 ? O2 Cu2 O2 90.1(3) . 12 ? O6 Cu2 O1W 95.9(2) 12 . ? O6 Cu2 O1W 95.9(2) . . ? O2 Cu2 O1W 96.7(3) . . ? O2 Cu2 O1W 96.7(3) 12 . ? O6 Cu2 Cu3 81.89(17) 12 . ? O6 Cu2 Cu3 81.89(17) . . ? O2 Cu2 Cu3 85.59(18) . . ? O2 Cu2 Cu3 85.59(18) 12 . ? O1W Cu2 Cu3 176.8(3) . . ? O1 Cu3 O1 90.3(4) 12 . ? O1 Cu3 O5 88.2(3) 12 12 ? O1 Cu3 O5 167.7(3) . 12 ? O1 Cu3 O5 167.7(3) 12 . ? O1 Cu3 O5 88.2(3) . . ? O5 Cu3 O5 90.7(4) 12 . ? O1 Cu3 O11 95.3(3) 12 . ? O1 Cu3 O11 95.3(3) . . ? O5 Cu3 O11 96.9(2) 12 . ? O5 Cu3 O11 96.9(2) . . ? O1 Cu3 Cu2 81.88(19) 12 . ? O1 Cu3 Cu2 81.88(19) . . ? O5 Cu3 Cu2 85.86(17) 12 . ? O5 Cu3 Cu2 85.86(17) . . ? O11 Cu3 Cu2 176.0(2) . . ? C2 C1 C6 120.4(7) . . ? C2 C1 C7 120.2(8) . . ? C6 C1 C7 119.1(7) . . ? C1 C2 C3 120.2(8) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.3(7) . . ? C4 C3 C8 120.4(7) . . ? C2 C3 C8 120.3(8) . . ? C3 C4 C5 120.5(8) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.3(10) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.2(8) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O2 C7 O1 125.9(8) . . ? O2 C7 C1 118.0(7) . . ? O1 C7 C1 116.1(8) . . ? O4 C8 O3 126.2(7) . . ? O4 C8 C3 117.9(7) . . ? O3 C8 C3 116.0(8) . . ? C14 C9 C10 119.7(7) . . ? C14 C9 C15 121.3(7) . . ? C10 C9 C15 119.0(8) . . ? C11 C10 C9 119.8(8) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 119.6(8) . . ? C12 C11 C16 120.3(7) . . ? C10 C11 C16 120.1(8) . . ? C13 C12 C11 121.1(8) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.3(9) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C9 C14 C13 120.4(8) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? O5 C15 O6 125.6(7) . . ? O5 C15 C9 118.1(7) . . ? O6 C15 C9 116.2(7) . . ? O7 C16 O8 126.3(8) . . ? O7 C16 C11 117.4(7) . . ? O8 C16 C11 116.2(8) . . ? O9 C17 N1 126.0(9) . . ? N2 C20 O10 130.1(17) . . ? C17 N1 C19 122.9(10) . . ? C17 N1 C18 120.0(10) . . ? C19 N1 C18 117.1(10) . . ? C20 N2 C22 117.6(15) . . ? C20 N2 C21 115.5(19) . . ? C22 N2 C21 126.7(15) . . ? C7 O1 Cu3 126.0(6) . . ? C7 O2 Cu2 119.7(5) . . ? C8 O3 Cu1 124.9(6) . . ? C8 O4 Cu1 120.3(5) . 7_545 ? C15 O5 Cu3 120.8(5) . . ? C15 O6 Cu2 125.4(6) . . ? C16 O7 Cu1 121.5(5) . 16_545 ? C16 O8 Cu1 124.0(6) . 10_556 ? C17 O9 Cu1 120.8(6) . . ? C24 O11 Cu3 134.6(8) . . ? Cu2 O1W H1WA 138.1 . . ? Cu2 O1W H1WB 111.6 . . ? H1WA O1W H1WB 110.3 . . ? O11 C24 C23 128.5(14) . . ? 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 O6 Cu2 Cu3 O1 87.8(3) 12 . . 12 ? O6 Cu2 Cu3 O1 -179.3(3) . . . 12 ? O2 Cu2 Cu3 O1 -90.9(3) . . . 12 ? O2 Cu2 Cu3 O1 -0.5(3) 12 . . 12 ? O1W Cu2 Cu3 O1 134.3(2) . . . 12 ? O6 Cu2 Cu3 O1 179.3(3) 12 . . . ? O6 Cu2 Cu3 O1 -87.8(3) . . . . ? O2 Cu2 Cu3 O1 0.5(3) . . . . ? O2 Cu2 Cu3 O1 90.9(3) 12 . . . ? O1W Cu2 Cu3 O1 -134.3(2) . . . . ? O6 Cu2 Cu3 O5 -1.0(3) 12 . . 12 ? O6 Cu2 Cu3 O5 92.0(3) . . . 12 ? O2 Cu2 Cu3 O5 -179.7(2) . . . 12 ? O2 Cu2 Cu3 O5 -89.3(3) 12 . . 12 ? O1W Cu2 Cu3 O5 45.49(18) . . . 12 ? O6 Cu2 Cu3 O5 -92.0(3) 12 . . . ? O6 Cu2 Cu3 O5 1.0(3) . . . . ? O2 Cu2 Cu3 O5 89.3(3) . . . . ? O2 Cu2 Cu3 O5 179.7(2) 12 . . . ? O1W Cu2 Cu3 O5 -45.49(18) . . . . ? O6 Cu2 Cu3 O11 133.52(18) 12 . . . ? O6 Cu2 Cu3 O11 -133.52(18) . . . . ? O2 Cu2 Cu3 O11 -45.20(17) . . . . ? O2 Cu2 Cu3 O11 45.20(17) 12 . . . ? O1W Cu2 Cu3 O11 180.000(19) . . . . ? C6 C1 C2 C3 0.6(13) . . . . ? C7 C1 C2 C3 174.7(7) . . . . ? C1 C2 C3 C4 -1.4(12) . . . . ? C1 C2 C3 C8 -178.0(7) . . . . ? C2 C3 C4 C5 2.3(14) . . . . ? C8 C3 C4 C5 178.9(9) . . . . ? C3 C4 C5 C6 -2.3(17) . . . . ? C4 C5 C6 C1 1.4(18) . . . . ? C2 C1 C6 C5 -0.5(16) . . . . ? C7 C1 C6 C5 -174.8(10) . . . . ? C2 C1 C7 O2 4.8(12) . . . . ? C6 C1 C7 O2 179.0(8) . . . . ? C2 C1 C7 O1 -175.8(7) . . . . ? C6 C1 C7 O1 -1.5(12) . . . . ? C4 C3 C8 O4 -173.5(8) . . . . ? C2 C3 C8 O4 3.1(11) . . . . ? C4 C3 C8 O3 6.8(12) . . . . ? C2 C3 C8 O3 -176.6(7) . . . . ? C14 C9 C10 C11 -1.1(13) . . . . ? C15 C9 C10 C11 179.6(7) . . . . ? C9 C10 C11 C12 0.3(13) . . . . ? C9 C10 C11 C16 -178.6(7) . . . . ? C10 C11 C12 C13 -0.1(16) . . . . ? C16 C11 C12 C13 178.7(10) . . . . ? C11 C12 C13 C14 0.8(17) . . . . ? C10 C9 C14 C13 1.7(15) . . . . ? C15 C9 C14 C13 -179.0(9) . . . . ? C12 C13 C14 C9 -1.6(17) . . . . ? C14 C9 C15 O5 -165.9(8) . . . . ? C10 C9 C15 O5 13.4(12) . . . . ? C14 C9 C15 O6 15.1(12) . . . . ? C10 C9 C15 O6 -165.7(7) . . . . ? C12 C11 C16 O7 177.9(9) . . . . ? C10 C11 C16 O7 -3.3(12) . . . . ? C12 C11 C16 O8 1.6(13) . . . . ? C10 C11 C16 O8 -179.6(8) . . . . ? O9 C17 N1 C19 -177.9(13) . . . . ? O9 C17 N1 C18 1.9(15) . . . . ? O10 C20 N2 C22 -159(3) . . . . ? O10 C20 N2 C21 26(5) . . . . ? O2 C7 O1 Cu3 -11.9(13) . . . . ? C1 C7 O1 Cu3 168.7(5) . . . . ? O1 Cu3 O1 C7 86.7(7) 12 . . . ? O5 Cu3 O1 C7 3.8(17) 12 . . . ? O5 Cu3 O1 C7 -81.1(7) . . . . ? O11 Cu3 O1 C7 -177.9(7) . . . . ? Cu2 Cu3 O1 C7 4.9(7) . . . . ? O1 C7 O2 Cu2 11.9(12) . . . . ? C1 C7 O2 Cu2 -168.7(5) . . . . ? O6 Cu2 O2 C7 -11.7(15) 12 . . . ? O6 Cu2 O2 C7 76.1(6) . . . . ? O2 Cu2 O2 C7 -91.5(6) 12 . . . ? O1W Cu2 O2 C7 171.8(6) . . . . ? Cu3 Cu2 O2 C7 -5.9(6) . . . . ? O4 C8 O3 Cu1 3.0(12) . . . . ? C3 C8 O3 Cu1 -177.3(5) . . . . ? O4 Cu1 O3 C8 89.0(7) 7_545 . . . ? O8 Cu1 O3 C8 -81.5(7) 10_566 . . . ? O7 Cu1 O3 C8 4.0(14) 16 . . . ? O9 Cu1 O3 C8 -175.3(7) . . . . ? Cu1 Cu1 O3 C8 1.8(6) 7_545 . . . ? O3 C8 O4 Cu1 -7.8(12) . . . 7_545 ? C3 C8 O4 Cu1 172.5(5) . . . 7_545 ? O6 C15 O5 Cu3 8.2(12) . . . . ? C9 C15 O5 Cu3 -170.8(5) . . . . ? O1 Cu3 O5 C15 -5.8(16) 12 . . . ? O1 Cu3 O5 C15 77.4(7) . . . . ? O5 Cu3 O5 C15 -90.4(6) 12 . . . ? O11 Cu3 O5 C15 172.5(6) . . . . ? Cu2 Cu3 O5 C15 -4.6(6) . . . . ? O5 C15 O6 Cu2 -7.1(13) . . . . ? C9 C15 O6 Cu2 171.9(5) . . . . ? O6 Cu2 O6 C15 83.9(7) 12 . . . ? O2 Cu2 O6 C15 -83.5(7) . . . . ? O2 Cu2 O6 C15 -3.5(16) 12 . . . ? O1W Cu2 O6 C15 -180.0(7) . . . . ? Cu3 Cu2 O6 C15 2.4(6) . . . . ? O8 C16 O7 Cu1 -0.2(13) . . . 16_545 ? C11 C16 O7 Cu1 -176.0(5) . . . 16_545 ? O7 C16 O8 Cu1 5.0(13) . . . 10_556 ? C11 C16 O8 Cu1 -179.1(5) . . . 10_556 ? N1 C17 O9 Cu1 -162.4(7) . . . . ? O4 Cu1 O9 C17 154.6(7) 7_545 . . . ? O8 Cu1 O9 C17 -23.8(7) 10_566 . . . ? O7 Cu1 O9 C17 -114.1(7) 16 . . . ? O3 Cu1 O9 C17 65.7(7) . . . . ? Cu1 Cu1 O9 C17 45.2(16) 7_545 . . . ? O1 Cu3 O11 C24 45.4(2) 12 . . . ? O1 Cu3 O11 C24 -45.4(2) . . . . ? O5 Cu3 O11 C24 134.23(18) 12 . . . ? O5 Cu3 O11 C24 -134.23(18) . . . . ? Cu2 Cu3 O11 C24 0.000(19) . . . . ? Cu3 O11 C24 C23 0.000(7) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 1.673 _refine_diff_density_min -3.286 _refine_diff_density_rms 0.154 data_5 _database_code_depnum_ccdc_archive 'CCDC 735406' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H35 Cu4 N2 O22.50' _chemical_formula_weight 1109.82 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 MONOCLINIC _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 17.781(4) _cell_length_b 28.331(6) _cell_length_c 10.766(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.92(3) _cell_angle_gamma 90.00 _cell_volume 5306.2(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 562 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2244 _exptl_absorpt_coefficient_mu 1.653 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7558 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; Refinement using reflections with F^2^ > -3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _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 ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19882 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.20 _reflns_number_total 4869 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku RAXIS-RAPID' _computing_cell_refinement 'Rigaku RAXIS-RAPID' _computing_data_reduction 'Rigaku RAXIS-RAPID' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1072P)^2^+8.9044P] 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 4869 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1790 _refine_ls_wR_factor_gt 0.1645 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.79169(3) 0.780608(17) 0.95029(5) 0.0334(2) Uani 1 1 d . . . Cu2 Cu 0.49985(4) 0.5000 0.37830(6) 0.0360(2) Uani 1 2 d S . . Cu3 Cu 1.07591(4) 0.5000 1.53041(8) 0.0424(2) Uani 1 2 d S . . C1 C 0.9388(3) 0.67659(18) 1.1579(5) 0.0475(11) Uani 1 1 d . . . C2 C 0.9365(3) 0.63354(18) 1.2185(5) 0.0495(12) Uani 1 1 d . . . H2 H 0.8894 0.6200 1.2225 0.059 Uiso 1 1 calc R . . C3 C 1.0042(3) 0.61077(19) 1.2730(5) 0.0515(12) Uani 1 1 d . . . C4 C 1.0744(3) 0.6317(3) 1.2683(7) 0.082(2) Uani 1 1 d . . . H4 H 1.1201 0.6167 1.3051 0.098 Uiso 1 1 calc R . . C5 C 1.0760(4) 0.6749(3) 1.2086(8) 0.106(3) Uani 1 1 d . . . H5 H 1.1229 0.6888 1.2053 0.127 Uiso 1 1 calc R . . C6 C 1.0085(3) 0.6974(2) 1.1542(6) 0.074(2) Uani 1 1 d . . . H6 H 1.0100 0.7266 1.1150 0.089 Uiso 1 1 calc R . . C7 C 0.8663(3) 0.70200(17) 1.0981(4) 0.0419(10) Uani 1 1 d . . . C8 C 1.0019(3) 0.56591(18) 1.3472(5) 0.0499(12) Uani 1 1 d . . . C9 C 0.7111(3) 0.67286(16) 0.6773(4) 0.0400(10) Uani 1 1 d . . . C10 C 0.6668(3) 0.63168(15) 0.6642(4) 0.0400(10) Uani 1 1 d . . . H10 H 0.6471 0.6206 0.7323 0.048 Uiso 1 1 calc R . . C11 C 0.6523(3) 0.60718(16) 0.5498(4) 0.0436(11) Uani 1 1 d . . . C12 C 0.6842(3) 0.6231(2) 0.4495(5) 0.0567(13) Uani 1 1 d . . . H12 H 0.6759 0.6065 0.3735 0.068 Uiso 1 1 calc R . . C13 C 0.7283(4) 0.6637(2) 0.4634(5) 0.0653(16) Uani 1 1 d . . . H13 H 0.7490 0.6744 0.3960 0.078 Uiso 1 1 calc R . . C14 C 0.7417(3) 0.68850(18) 0.5756(4) 0.0531(13) Uani 1 1 d . . . H14 H 0.7714 0.7158 0.5837 0.064 Uiso 1 1 calc R . . C15 C 0.7243(2) 0.70066(16) 0.7993(4) 0.0389(10) Uani 1 1 d . . . C16 C 0.5991(3) 0.56509(16) 0.5335(4) 0.0425(10) Uani 1 1 d . . . C17 C 0.9271(3) 0.8356(2) 0.8380(5) 0.0601(14) Uani 1 1 d . . . C18 C 0.9949(4) 0.8544(4) 0.7972(8) 0.121(3) Uani 1 1 d . . . H18A H 1.0385 0.8531 0.8667 0.145 Uiso 1 1 calc R . . H18B H 0.9856 0.8866 0.7704 0.145 Uiso 1 1 calc R . . H18C H 1.0051 0.8359 0.7279 0.145 Uiso 1 1 calc R . . N1 N 0.8759(3) 0.82195(16) 0.8713(4) 0.0533(11) Uani 1 1 d . . . O1 O 0.87316(18) 0.73792(12) 1.0344(3) 0.0471(8) Uani 1 1 d . . . O2 O 0.80324(19) 0.68469(11) 1.1149(3) 0.0487(8) Uani 1 1 d . . . O3 O 0.9371(2) 0.54916(13) 1.3485(4) 0.0598(10) Uani 1 1 d . . . O4 O 1.0655(2) 0.54935(13) 1.4013(4) 0.0648(10) Uani 1 1 d . . . O5 O 0.76366(19) 0.73745(11) 0.8033(3) 0.0454(8) Uani 1 1 d . . . O6 O 0.69631(19) 0.68438(11) 0.8888(3) 0.0493(8) Uani 1 1 d . . . O7 O 0.5788(2) 0.54946(12) 0.6301(3) 0.0507(8) Uani 1 1 d . . . O8 O 0.5788(2) 0.54905(11) 0.4228(3) 0.0509(9) Uani 1 1 d . . . O1W O 0.4999(4) 0.5000 0.1788(5) 0.0802(18) Uani 1 2 d S . . H1WA H 0.5380 0.5000 0.1374 0.096 Uiso 1 2 d SR . . H1WB H 0.4626 0.5000 0.1106 0.096 Uiso 1 2 d SR . . O2W O 1.2030(4) 0.5000 1.5718(9) 0.116(3) Uani 1 2 d S . . H2WB H 1.2192 0.5000 1.5058 0.139 Uiso 1 2 d SR . . H2WA H 1.2378 0.5000 1.6344 0.139 Uiso 1 2 d SR . . O5W O 0.3966(16) 0.4413(9) 0.986(2) 0.159(8) Uiso 0.33 1 d P A 1 O5W' O 0.3276(17) 0.4340(10) 0.981(2) 0.161(8) Uiso 0.33 1 d P B 1 O5W" O 0.2635(15) 0.4299(9) 0.897(2) 0.158(8) Uiso 0.33 1 d P C 2 O3W O 0.2343(11) 0.5000 0.3263(18) 0.264(8) Uiso 1 2 d S . . O4W O 1.0000 0.7978(10) 0.5000 0.165(9) Uiso 0.50 2 d SP D 1 O4W' O 0.960(2) 0.7178(14) 0.490(4) 0.192(15) Uiso 0.25 1 d P . 1 O4W" O 1.0000 0.7620(13) 0.5000 0.093(8) Uiso 0.25 2 d SP E 2 O6W O 0.0000 0.5000 0.0000 0.25(2) Uiso 0.50 4 d SP . . 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 0.0336(3) 0.0243(3) 0.0419(3) 0.00116(19) 0.0065(2) -0.0044(2) Cu2 0.0498(5) 0.0247(4) 0.0312(4) 0.000 0.0031(3) 0.000 Cu3 0.0361(5) 0.0239(4) 0.0609(5) 0.000 -0.0048(3) 0.000 C1 0.040(3) 0.042(3) 0.057(3) 0.012(2) 0.003(2) 0.001(2) C2 0.038(3) 0.043(3) 0.065(3) 0.010(2) 0.004(2) -0.001(2) C3 0.045(3) 0.045(3) 0.061(3) 0.017(2) 0.002(2) 0.004(2) C4 0.041(3) 0.087(5) 0.113(5) 0.054(4) 0.007(3) 0.006(3) C5 0.041(3) 0.121(7) 0.148(7) 0.090(6) 0.003(4) -0.006(4) C6 0.043(3) 0.077(4) 0.096(4) 0.053(4) 0.002(3) -0.009(3) C7 0.039(3) 0.037(3) 0.045(2) 0.006(2) 0.0007(18) 0.001(2) C8 0.045(3) 0.032(3) 0.069(3) 0.008(2) 0.003(2) 0.008(2) C9 0.041(2) 0.033(2) 0.045(2) -0.0035(19) 0.0052(18) -0.0032(19) C10 0.043(2) 0.031(2) 0.044(2) -0.0029(18) 0.0053(18) 0.000(2) C11 0.046(3) 0.033(2) 0.050(3) -0.002(2) 0.005(2) -0.005(2) C12 0.070(3) 0.055(3) 0.046(3) -0.009(2) 0.012(2) -0.015(3) C13 0.085(4) 0.063(4) 0.051(3) -0.005(3) 0.022(3) -0.033(3) C14 0.065(3) 0.043(3) 0.049(3) -0.001(2) 0.005(2) -0.018(2) C15 0.033(2) 0.035(2) 0.047(2) -0.0044(19) 0.0035(18) -0.0054(19) C16 0.051(3) 0.027(2) 0.046(3) -0.0040(19) 0.002(2) 0.001(2) C17 0.052(3) 0.064(4) 0.065(3) 0.014(3) 0.012(2) -0.009(3) C18 0.066(5) 0.169(10) 0.134(7) 0.058(7) 0.035(4) -0.024(5) N1 0.051(3) 0.050(3) 0.062(3) 0.011(2) 0.017(2) -0.014(2) O1 0.0423(18) 0.0407(19) 0.057(2) 0.0161(15) 0.0080(14) 0.0039(15) O2 0.0450(19) 0.0331(18) 0.067(2) 0.0119(15) 0.0088(15) 0.0022(15) O3 0.047(2) 0.044(2) 0.081(2) 0.0202(18) -0.0021(17) -0.0005(17) O4 0.049(2) 0.052(2) 0.088(3) 0.026(2) 0.0020(18) 0.0060(18) O5 0.0491(19) 0.0381(18) 0.0494(18) -0.0094(14) 0.0109(14) -0.0116(15) O6 0.057(2) 0.0403(19) 0.0517(18) -0.0097(15) 0.0152(15) -0.0153(16) O7 0.065(2) 0.0408(19) 0.0438(18) -0.0054(14) 0.0049(15) -0.0134(16) O8 0.065(2) 0.0404(19) 0.0449(18) -0.0098(14) 0.0070(15) -0.0160(17) O1W 0.109(5) 0.094(5) 0.036(3) 0.000 0.011(3) 0.000 O2W 0.054(4) 0.125(7) 0.156(7) 0.000 -0.007(4) 0.000 _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 1.954(3) 7_667 ? Cu1 O1 1.959(3) . ? Cu1 O6 1.969(3) 7_667 ? Cu1 O5 1.980(3) . ? Cu1 N1 2.206(4) . ? Cu1 Cu1 2.6469(11) 7_667 ? Cu2 O8 1.964(3) . ? Cu2 O8 1.964(3) 6_565 ? Cu2 O7 1.969(3) 5_666 ? Cu2 O7 1.969(3) 2_656 ? Cu2 O1W 2.147(5) . ? Cu2 Cu2 2.6193(15) 5_666 ? Cu3 O4 1.953(4) 6_565 ? Cu3 O4 1.953(4) . ? Cu3 O3 1.954(4) 2_758 ? Cu3 O3 1.954(4) 5_768 ? Cu3 O2W 2.211(7) . ? Cu3 Cu3 2.6429(16) 5_768 ? C1 C6 1.382(7) . ? C1 C2 1.388(7) . ? C1 C7 1.500(6) . ? C2 C3 1.386(6) . ? C2 H2 0.9300 . ? C3 C4 1.392(8) . ? C3 C8 1.506(7) . ? C4 C5 1.385(9) . ? C4 H4 0.9300 . ? C5 C6 1.378(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.247(6) . ? C7 O2 1.271(6) . ? C8 O3 1.249(6) . ? C8 O4 1.252(6) . ? C9 C14 1.392(7) . ? C9 C10 1.398(6) . ? C9 C15 1.508(6) . ? C10 C11 1.391(6) . ? C10 H10 0.9300 . ? C11 C12 1.395(7) . ? C11 C16 1.510(6) . ? C12 C13 1.382(7) . ? C12 H12 0.9300 . ? C13 C14 1.375(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O5 1.251(5) . ? C15 O6 1.259(5) . ? C16 O7 1.250(6) . ? C16 O8 1.257(5) . ? C17 N1 1.115(6) . ? C17 C18 1.466(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O2 Cu1 1.954(3) 7_667 ? O3 Cu3 1.954(4) 5_768 ? O6 Cu1 1.969(3) 7_667 ? O7 Cu2 1.969(3) 5_666 ? O1W H1WA 0.8856 . ? O1W H1WB 0.8818 . ? O2W H2WB 0.8191 . ? O2W H2WA 0.8164 . ? O4W' O4W' 1.38(7) 2_756 ? 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 O1 167.92(14) 7_667 . ? O2 Cu1 O6 89.50(15) 7_667 7_667 ? O1 Cu1 O6 88.22(15) . 7_667 ? O2 Cu1 O5 88.14(15) 7_667 . ? O1 Cu1 O5 91.61(14) . . ? O6 Cu1 O5 167.85(13) 7_667 . ? O2 Cu1 N1 101.49(15) 7_667 . ? O1 Cu1 N1 90.55(15) . . ? O6 Cu1 N1 96.47(15) 7_667 . ? O5 Cu1 N1 95.68(15) . . ? O2 Cu1 Cu1 87.74(10) 7_667 7_667 ? O1 Cu1 Cu1 80.28(10) . 7_667 ? O6 Cu1 Cu1 86.70(10) 7_667 7_667 ? O5 Cu1 Cu1 81.31(10) . 7_667 ? N1 Cu1 Cu1 170.23(12) . 7_667 ? O8 Cu2 O8 90.1(2) . 6_565 ? O8 Cu2 O7 168.69(14) . 5_666 ? O8 Cu2 O7 88.46(15) 6_565 5_666 ? O8 Cu2 O7 88.46(15) . 2_656 ? O8 Cu2 O7 168.69(14) 6_565 2_656 ? O7 Cu2 O7 90.8(2) 5_666 2_656 ? O8 Cu2 O1W 95.52(16) . . ? O8 Cu2 O1W 95.52(16) 6_565 . ? O7 Cu2 O1W 95.79(16) 5_666 . ? O7 Cu2 O1W 95.79(16) 2_656 . ? O8 Cu2 Cu2 84.40(10) . 5_666 ? O8 Cu2 Cu2 84.40(10) 6_565 5_666 ? O7 Cu2 Cu2 84.29(10) 5_666 5_666 ? O7 Cu2 Cu2 84.29(10) 2_656 5_666 ? O1W Cu2 Cu2 179.88(19) . 5_666 ? O4 Cu3 O4 91.4(3) 6_565 . ? O4 Cu3 O3 168.04(16) 6_565 2_758 ? O4 Cu3 O3 87.60(18) . 2_758 ? O4 Cu3 O3 87.60(18) 6_565 5_768 ? O4 Cu3 O3 168.04(16) . 5_768 ? O3 Cu3 O3 90.9(2) 2_758 5_768 ? O4 Cu3 O2W 94.9(2) 6_565 . ? O4 Cu3 O2W 94.9(2) . . ? O3 Cu3 O2W 97.1(2) 2_758 . ? O3 Cu3 O2W 97.1(2) 5_768 . ? O4 Cu3 Cu3 83.24(11) 6_565 5_768 ? O4 Cu3 Cu3 83.24(11) . 5_768 ? O3 Cu3 Cu3 84.81(11) 2_758 5_768 ? O3 Cu3 Cu3 84.81(11) 5_768 5_768 ? O2W Cu3 Cu3 177.3(3) . 5_768 ? C6 C1 C2 120.2(4) . . ? C6 C1 C7 118.7(4) . . ? C2 C1 C7 121.2(4) . . ? C3 C2 C1 120.1(5) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.6(5) . . ? C2 C3 C8 120.1(5) . . ? C4 C3 C8 120.1(4) . . ? C5 C4 C3 119.8(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 120.5(6) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.9(5) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 O2 125.6(4) . . ? O1 C7 C1 117.0(4) . . ? O2 C7 C1 117.3(4) . . ? O3 C8 O4 126.9(5) . . ? O3 C8 C3 116.9(4) . . ? O4 C8 C3 116.2(5) . . ? C14 C9 C10 119.3(4) . . ? C14 C9 C15 120.2(4) . . ? C10 C9 C15 120.5(4) . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.5(4) . . ? C10 C11 C16 119.6(4) . . ? C12 C11 C16 120.8(4) . . ? C13 C12 C11 119.9(5) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.8(5) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 120.2(5) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O5 C15 O6 125.8(4) . . ? O5 C15 C9 116.8(4) . . ? O6 C15 C9 117.4(4) . . ? O7 C16 O8 125.8(4) . . ? O7 C16 C11 117.7(4) . . ? O8 C16 C11 116.4(4) . . ? N1 C17 C18 178.4(8) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 N1 Cu1 166.7(5) . . ? C7 O1 Cu1 127.6(3) . . ? C7 O2 Cu1 118.5(3) . 7_667 ? C8 O3 Cu3 121.0(3) . 5_768 ? C8 O4 Cu3 122.9(4) . . ? C15 O5 Cu1 126.1(3) . . ? C15 O6 Cu1 120.0(3) . 7_667 ? C16 O7 Cu2 122.6(3) . 5_666 ? C16 O8 Cu2 122.5(3) . . ? Cu2 O1W H1WA 131.5 . . ? Cu2 O1W H1WB 132.6 . . ? H1WA O1W H1WB 95.9 . . ? Cu3 O2W H2WB 110.7 . . ? Cu3 O2W H2WA 137.4 . . ? H2WB O2W H2WA 111.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.5(8) . . . . ? C7 C1 C2 C3 -180.0(5) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? C1 C2 C3 C8 175.4(5) . . . . ? C2 C3 C4 C5 -0.3(11) . . . . ? C8 C3 C4 C5 -174.8(7) . . . . ? C3 C4 C5 C6 0.2(14) . . . . ? C4 C5 C6 C1 -0.7(13) . . . . ? C2 C1 C6 C5 1.3(11) . . . . ? C7 C1 C6 C5 179.8(7) . . . . ? C6 C1 C7 O1 8.7(8) . . . . ? C2 C1 C7 O1 -172.8(5) . . . . ? C6 C1 C7 O2 -172.4(5) . . . . ? C2 C1 C7 O2 6.1(7) . . . . ? C2 C3 C8 O3 5.1(8) . . . . ? C4 C3 C8 O3 179.5(6) . . . . ? C2 C3 C8 O4 -175.0(5) . . . . ? C4 C3 C8 O4 -0.6(8) . . . . ? C14 C9 C10 C11 -1.4(7) . . . . ? C15 C9 C10 C11 177.4(4) . . . . ? C9 C10 C11 C12 2.1(7) . . . . ? C9 C10 C11 C16 -174.9(4) . . . . ? C10 C11 C12 C13 -1.7(8) . . . . ? C16 C11 C12 C13 175.3(5) . . . . ? C11 C12 C13 C14 0.7(9) . . . . ? C12 C13 C14 C9 0.1(9) . . . . ? C10 C9 C14 C13 0.3(8) . . . . ? C15 C9 C14 C13 -178.5(5) . . . . ? C14 C9 C15 O5 -0.3(7) . . . . ? C10 C9 C15 O5 -179.1(4) . . . . ? C14 C9 C15 O6 -178.8(5) . . . . ? C10 C9 C15 O6 2.4(6) . . . . ? C10 C11 C16 O7 -10.4(7) . . . . ? C12 C11 C16 O7 172.6(5) . . . . ? C10 C11 C16 O8 169.3(4) . . . . ? C12 C11 C16 O8 -7.7(7) . . . . ? C18 C17 N1 Cu1 -105(27) . . . . ? O2 Cu1 N1 C17 -166(2) 7_667 . . . ? O1 Cu1 N1 C17 15(2) . . . . ? O6 Cu1 N1 C17 103(2) 7_667 . . . ? O5 Cu1 N1 C17 -77(2) . . . . ? Cu1 Cu1 N1 C17 -5(3) 7_667 . . . ? O2 C7 O1 Cu1 4.1(7) . . . . ? C1 C7 O1 Cu1 -177.2(3) . . . . ? O2 Cu1 O1 C7 7.3(9) 7_667 . . . ? O6 Cu1 O1 C7 86.5(4) 7_667 . . . ? O5 Cu1 O1 C7 -81.4(4) . . . . ? N1 Cu1 O1 C7 -177.1(4) . . . . ? Cu1 Cu1 O1 C7 -0.5(4) 7_667 . . . ? O1 C7 O2 Cu1 -5.9(7) . . . 7_667 ? C1 C7 O2 Cu1 175.3(3) . . . 7_667 ? O4 C8 O3 Cu3 13.9(8) . . . 5_768 ? C3 C8 O3 Cu3 -166.2(4) . . . 5_768 ? O3 C8 O4 Cu3 -13.5(8) . . . . ? C3 C8 O4 Cu3 166.5(4) . . . . ? O4 Cu3 O4 C8 88.7(5) 6_565 . . . ? O3 Cu3 O4 C8 -79.4(5) 2_758 . . . ? O3 Cu3 O4 C8 3.7(11) 5_768 . . . ? O2W Cu3 O4 C8 -176.2(5) . . . . ? Cu3 Cu3 O4 C8 5.7(4) 5_768 . . . ? O6 C15 O5 Cu1 -0.9(7) . . . . ? C9 C15 O5 Cu1 -179.2(3) . . . . ? O2 Cu1 O5 C15 -89.3(4) 7_667 . . . ? O1 Cu1 O5 C15 78.6(4) . . . . ? O6 Cu1 O5 C15 -10.4(9) 7_667 . . . ? N1 Cu1 O5 C15 169.3(4) . . . . ? Cu1 Cu1 O5 C15 -1.3(4) 7_667 . . . ? O5 C15 O6 Cu1 3.5(7) . . . 7_667 ? C9 C15 O6 Cu1 -178.2(3) . . . 7_667 ? O8 C16 O7 Cu2 -7.3(7) . . . 5_666 ? C11 C16 O7 Cu2 172.4(3) . . . 5_666 ? O7 C16 O8 Cu2 7.8(7) . . . . ? C11 C16 O8 Cu2 -171.9(3) . . . . ? O8 Cu2 O8 C16 -88.2(4) 6_565 . . . ? O7 Cu2 O8 C16 -5.6(10) 5_666 . . . ? O7 Cu2 O8 C16 80.6(4) 2_656 . . . ? O1W Cu2 O8 C16 176.2(4) . . . . ? Cu2 Cu2 O8 C16 -3.8(4) 5_666 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.855 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.105