data_280922d_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H24 Cu2 N8 O12' _chemical_formula_sum 'C32 H24 Cu2 N8 O12' _chemical_formula_weight 839.69 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7302(12) _cell_length_b 8.2404(12) _cell_length_c 13.782(2) _cell_angle_alpha 89.723(2) _cell_angle_beta 83.928(1) _cell_angle_gamma 62.528(2) _cell_volume 773.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 904 _cell_measurement_theta_min 2.790 _cell_measurement_theta_max 21.371 _exptl_crystal_description block _exptl_crystal_colour 'red brown' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 426 _exptl_absorpt_coefficient_mu 1.459 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8218 _exptl_absorpt_correction_T_max 0.8678 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w 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 3870 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2679 _reflns_number_gt 1790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _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^)+(0.0740P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2679 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 0.32142(10) -0.03317(9) 0.53785(5) 0.0329(3) Uani 1 1 d . . . C1 C -0.1181(7) 0.1856(7) 0.6511(4) 0.0266(12) Uani 1 1 d . . . C2 C -0.3213(8) 0.2866(7) 0.6974(4) 0.0271(12) Uani 1 1 d . . . C3 C -0.2307(7) 0.0903(7) 0.8343(4) 0.0274(13) Uani 1 1 d . . . C4 C -0.0357(8) -0.0089(7) 0.7907(4) 0.0291(13) Uani 1 1 d . . . C5 C 0.0254(8) 0.0409(8) 0.6981(4) 0.0311(13) Uani 1 1 d . . . C6 C -0.2849(8) 0.0389(8) 0.9240(4) 0.0386(15) Uani 1 1 d . . . H6 H -0.4130 0.1043 0.9539 0.046 Uiso 1 1 calc R . . C7 C -0.1502(9) -0.1085(8) 0.9691(5) 0.0429(16) Uani 1 1 d . . . H7 H -0.1890 -0.1418 1.0289 0.052 Uiso 1 1 calc R . . C8 C 0.0407(9) -0.2068(8) 0.9266(5) 0.0429(16) Uani 1 1 d . . . H8 H 0.1307 -0.3054 0.9576 0.051 Uiso 1 1 calc R . . C9 C 0.0971(8) -0.1579(8) 0.8379(4) 0.0364(15) Uani 1 1 d . . . H9 H 0.2257 -0.2250 0.8088 0.044 Uiso 1 1 calc R . . C10 C -0.5689(8) 0.3413(9) 0.8334(5) 0.0494(18) Uani 1 1 d . . . H10A H -0.6415 0.4424 0.7946 0.074 Uiso 1 1 calc R . . H10B H -0.5676 0.3868 0.8972 0.074 Uiso 1 1 calc R . . H10C H -0.6299 0.2627 0.8392 0.074 Uiso 1 1 calc R . . C11 C 0.1021(7) 0.2506(7) 0.4226(4) 0.0256(12) Uani 1 1 d . . . C12 C 0.2931(7) 0.1506(7) 0.3707(4) 0.0242(12) Uani 1 1 d . . . C13 C 0.3328(8) 0.2141(7) 0.2819(4) 0.0301(13) Uani 1 1 d . . . H13 H 0.4555 0.1527 0.2457 0.036 Uiso 1 1 calc R . . C14 C 0.1876(8) 0.3692(7) 0.2487(4) 0.0315(14) Uani 1 1 d . . . C15 C 0.0025(8) 0.4695(8) 0.3000(4) 0.0342(14) Uani 1 1 d . . . H15 H -0.0904 0.5759 0.2756 0.041 Uiso 1 1 calc R . . C16 C -0.0401(8) 0.4086(7) 0.3870(4) 0.0340(14) Uani 1 1 d . . . H16 H -0.1635 0.4723 0.4223 0.041 Uiso 1 1 calc R . . N1 N 0.0810(6) 0.1743(6) 0.5112(3) 0.0275(10) Uani 1 1 d . . . N2 N -0.0906(6) 0.2485(6) 0.5607(3) 0.0277(11) Uani 1 1 d . . . N3 N -0.3660(6) 0.2373(6) 0.7861(3) 0.0294(11) Uani 1 1 d . . . N4 N 0.2316(8) 0.4333(7) 0.1533(4) 0.0420(13) Uani 1 1 d . . . O1 O 0.2066(5) -0.0530(6) 0.6627(3) 0.0415(11) Uani 1 1 d . . . O2 O -0.4503(5) 0.4143(5) 0.6564(3) 0.0344(10) Uani 1 1 d . . . O3 O 0.3962(7) 0.3496(7) 0.1089(4) 0.0625(14) Uani 1 1 d . . . O4 O 0.1006(8) 0.5679(7) 0.1226(4) 0.0694(15) Uani 1 1 d . . . O5 O 0.4256(5) 0.0032(5) 0.4101(3) 0.0278(9) Uani 1 1 d . . . O6 O 0.5055(5) -0.3068(5) 0.5203(3) 0.0334(10) Uani 1 1 d . . . H6A H 0.4680 -0.3521 0.4767 0.050 Uiso 1 1 d R . . H6B H 0.5034 -0.3603 0.5729 0.050 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 0.0235(4) 0.0361(4) 0.0310(5) 0.0147(3) 0.0006(3) -0.0077(3) C1 0.021(3) 0.030(3) 0.026(3) 0.004(2) -0.003(2) -0.010(2) C2 0.026(3) 0.030(3) 0.023(3) 0.001(2) -0.003(2) -0.011(3) C3 0.025(3) 0.030(3) 0.025(3) 0.002(2) -0.001(2) -0.011(3) C4 0.028(3) 0.037(3) 0.023(3) 0.007(3) -0.005(2) -0.015(3) C5 0.029(3) 0.039(3) 0.026(3) 0.000(3) -0.006(3) -0.015(3) C6 0.030(3) 0.047(4) 0.034(4) 0.004(3) 0.006(3) -0.015(3) C7 0.044(4) 0.048(4) 0.035(4) 0.010(3) 0.001(3) -0.020(3) C8 0.040(4) 0.046(4) 0.034(4) 0.020(3) -0.006(3) -0.012(3) C9 0.028(3) 0.039(4) 0.034(4) 0.007(3) -0.001(3) -0.008(3) C10 0.024(3) 0.059(4) 0.042(4) 0.014(3) 0.007(3) -0.003(3) C11 0.026(3) 0.031(3) 0.022(3) 0.005(2) -0.005(2) -0.015(2) C12 0.026(3) 0.027(3) 0.023(3) 0.002(2) -0.002(2) -0.016(2) C13 0.032(3) 0.036(3) 0.024(3) 0.006(3) -0.001(2) -0.019(3) C14 0.042(4) 0.037(3) 0.027(3) 0.014(3) -0.009(3) -0.027(3) C15 0.038(3) 0.033(3) 0.032(4) 0.016(3) -0.010(3) -0.017(3) C16 0.027(3) 0.037(3) 0.034(4) 0.005(3) -0.005(3) -0.012(3) N1 0.024(2) 0.036(3) 0.023(3) 0.007(2) -0.002(2) -0.014(2) N2 0.024(2) 0.031(3) 0.026(3) 0.003(2) -0.001(2) -0.011(2) N3 0.026(2) 0.033(3) 0.023(3) 0.000(2) 0.002(2) -0.009(2) N4 0.056(4) 0.048(3) 0.034(3) 0.019(3) -0.007(3) -0.034(3) O1 0.025(2) 0.054(3) 0.031(2) 0.018(2) 0.0013(18) -0.0066(19) O2 0.026(2) 0.028(2) 0.039(3) 0.0123(18) -0.0007(18) -0.0046(18) O3 0.064(3) 0.077(4) 0.044(3) 0.023(3) 0.008(3) -0.033(3) O4 0.076(4) 0.071(4) 0.053(3) 0.040(3) -0.012(3) -0.027(3) O5 0.026(2) 0.028(2) 0.026(2) 0.0081(17) 0.0011(16) -0.0101(17) O6 0.045(2) 0.025(2) 0.033(2) 0.0078(17) -0.0086(19) -0.0177(19) _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 1.893(4) . ? Cu1 N1 1.928(4) . ? Cu1 O5 1.938(3) . ? Cu1 O6 2.034(3) . ? Cu1 O5 2.267(4) 2_656 ? Cu1 Cu1 3.1285(14) 2_656 ? C1 N2 1.380(7) . ? C1 C5 1.413(7) . ? C1 C2 1.468(7) . ? C2 O2 1.252(6) . ? C2 N3 1.346(7) . ? C3 C6 1.390(7) . ? C3 N3 1.405(6) . ? C3 C4 1.406(7) . ? C4 C9 1.398(7) . ? C4 C5 1.438(8) . ? C5 O1 1.287(6) . ? C6 C7 1.382(8) . ? C6 H6 0.9300 . ? C7 C8 1.377(8) . ? C7 H7 0.9300 . ? C8 C9 1.375(8) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N3 1.473(7) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.389(7) . ? C11 N1 1.399(7) . ? C11 C12 1.425(7) . ? C12 O5 1.335(6) . ? C12 C13 1.389(7) . ? C13 C14 1.372(7) . ? C13 H13 0.9300 . ? C14 C15 1.390(8) . ? C14 N4 1.479(7) . ? C15 C16 1.364(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N1 N2 1.290(6) . ? N4 O4 1.219(6) . ? N4 O3 1.224(6) . ? O5 Cu1 2.267(4) 2_656 ? O6 H6A 0.8501 . ? O6 H6B 0.8500 . ? 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 N1 91.75(17) . . ? O1 Cu1 O5 176.31(16) . . ? N1 Cu1 O5 84.77(17) . . ? O1 Cu1 O6 93.47(16) . . ? N1 Cu1 O6 148.93(18) . . ? O5 Cu1 O6 90.15(15) . . ? O1 Cu1 O5 96.70(15) . 2_656 ? N1 Cu1 O5 122.60(16) . 2_656 ? O5 Cu1 O5 84.18(15) . 2_656 ? O6 Cu1 O5 87.14(13) . 2_656 ? O1 Cu1 Cu1 134.64(13) . 2_656 ? N1 Cu1 Cu1 109.51(13) . 2_656 ? O5 Cu1 Cu1 46.14(11) . 2_656 ? O6 Cu1 Cu1 88.03(10) . 2_656 ? O5 Cu1 Cu1 38.04(9) 2_656 2_656 ? N2 C1 C5 126.7(5) . . ? N2 C1 C2 112.5(4) . . ? C5 C1 C2 120.9(5) . . ? O2 C2 N3 120.5(5) . . ? O2 C2 C1 121.6(5) . . ? N3 C2 C1 117.9(5) . . ? C6 C3 N3 121.6(5) . . ? C6 C3 C4 118.9(5) . . ? N3 C3 C4 119.5(5) . . ? C9 C4 C3 119.2(5) . . ? C9 C4 C5 120.5(5) . . ? C3 C4 C5 120.3(5) . . ? O1 C5 C1 124.6(5) . . ? O1 C5 C4 117.5(5) . . ? C1 C5 C4 117.9(5) . . ? C7 C6 C3 120.6(5) . . ? C7 C6 H6 119.7 . . ? C3 C6 H6 119.7 . . ? C8 C7 C6 120.8(6) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C7 119.4(5) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C4 121.1(5) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 N1 125.9(5) . . ? C16 C11 C12 121.6(5) . . ? N1 C11 C12 112.4(5) . . ? O5 C12 C13 123.3(5) . . ? O5 C12 C11 118.9(5) . . ? C13 C12 C11 117.9(5) . . ? C14 C13 C12 118.8(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 123.6(5) . . ? C13 C14 N4 118.0(5) . . ? C15 C14 N4 118.4(5) . . ? C16 C15 C14 118.6(5) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 119.6(5) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N2 N1 C11 117.1(4) . . ? N2 N1 Cu1 130.4(4) . . ? C11 N1 Cu1 112.5(3) . . ? N1 N2 C1 119.7(4) . . ? C2 N3 C3 123.4(4) . . ? C2 N3 C10 117.8(5) . . ? C3 N3 C10 118.8(5) . . ? O4 N4 O3 123.0(5) . . ? O4 N4 C14 117.9(5) . . ? O3 N4 C14 119.1(5) . . ? C5 O1 Cu1 126.5(4) . . ? C12 O5 Cu1 111.2(3) . . ? C12 O5 Cu1 115.4(3) . 2_656 ? Cu1 O5 Cu1 95.82(15) . 2_656 ? Cu1 O6 H6A 108.7 . . ? Cu1 O6 H6B 111.2 . . ? H6A O6 H6B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.495 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.122