data_50106am _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H16 Cu N2 O9' _chemical_formula_weight 563.95 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 'Trigonal' _symmetry_space_group_name_H-M 'P 31 2 1' _symmetry_space_group_name_Hall 'P 31 2"' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'y, x, -z' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' _cell_length_a 10.963(2) _cell_length_b 10.963(2) _cell_length_c 16.034(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1668.8(5) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 711 _cell_measurement_theta_min 2.493 _cell_measurement_theta_max 21.089 _exptl_crystal_description ? _exptl_crystal_colour dark blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 861 _exptl_absorpt_coefficient_mu 1.046 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.81 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9062 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0754 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.94 _reflns_number_total 2191 _reflns_number_gt 1811 _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^)+(0.1050P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.072(16) _chemical_absolute_configuration unk _refine_ls_number_reflns 2191 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1523 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 C1 C 0.6048(6) 0.8334(6) 0.0573(4) 0.0352(13) Uani 1 1 d . . . C2 C 0.6082(6) 0.7336(6) 0.0050(3) 0.0308(13) Uani 1 1 d . . . C3 C 0.4937(6) 0.6447(6) -0.0464(3) 0.0338(14) Uani 1 1 d . . . H3 H 0.4969 0.5742 -0.0769 0.041 Uiso 1 1 calc R . . C4 C 0.3792(6) 0.6601(6) -0.0521(3) 0.0344(13) Uani 1 1 d . . . H4 H 0.3027 0.5990 -0.0848 0.041 Uiso 1 1 calc R . . C5 C 0.3777(6) 0.7715(6) -0.0073(3) 0.0348(13) Uani 1 1 d . . . H5 H 0.3042 0.7897 -0.0145 0.042 Uiso 1 1 calc R . . C6 C 0.4860(7) 0.8518(6) 0.0466(3) 0.0375(14) Uani 1 1 d . . . C7 C 0.7152(7) 0.9021(7) 0.1211(4) 0.0334(13) Uani 1 1 d . . . C8 C 0.4814(7) 0.9704(7) 0.0901(4) 0.0361(14) Uani 1 1 d . . . C9 C 1.0405(6) 0.8656(6) 0.1001(4) 0.0334(13) Uani 1 1 d . . . H9 H 1.0695 0.9230 0.0531 0.040 Uiso 1 1 calc R . . C10 C 1.0419(6) 0.7407(6) 0.0967(3) 0.0289(12) Uani 1 1 d . . . H10 H 1.0704 0.7150 0.0484 0.035 Uiso 1 1 calc R . . C11 C 1.0000 0.6531(8) 0.1667 0.0282(17) Uani 1 2 d S . . C12 C 1.1064(6) 1.3839(6) 0.1333(4) 0.0331(13) Uani 1 1 d . . . H12 H 1.1828 1.3798 0.1113 0.040 Uiso 1 1 calc R . . C13 C 1.1065(7) 1.5070(8) 0.1303(4) 0.0404(14) Uani 1 1 d . . . H13 H 1.1795 1.5841 0.1034 0.048 Uiso 1 1 calc R . . C14 C 1.0000 1.5195(8) 0.1667 0.0297(17) Uani 1 2 d S . . Cu1 Cu 1.0000 1.08645(9) 0.1667 0.0305(3) Uani 1 2 d S . . N1 N 1.0000 0.9089(6) 0.1667 0.0312(16) Uani 1 2 d S . . N2 N 1.0000 1.2676(8) 0.1667 0.0375(18) Uani 1 2 d S . . O1 O 0.8299(4) 1.0035(4) 0.0992(2) 0.0362(9) Uani 1 1 d . . . O2 O 0.6854(5) 0.8534(4) 0.1911(2) 0.0341(10) Uani 1 1 d . . . O3 O 0.5828(4) 1.0545(4) 0.1324(2) 0.0291(9) Uani 1 1 d . . . O4 O 0.3717(4) 0.9753(4) 0.0797(2) 0.0277(8) Uani 1 1 d . . . H4A H 0.3536 1.0364 0.0995 0.033 Uiso 1 1 d R . . O5 O 0.7341(5) 0.7341(5) 0.0000 0.0324(13) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(3) 0.027(3) 0.035(3) 0.000(2) 0.006(3) 0.003(3) C2 0.030(3) 0.027(3) 0.029(3) 0.000(2) 0.006(2) 0.009(2) C3 0.041(4) 0.033(3) 0.033(3) -0.016(2) -0.005(2) 0.022(3) C4 0.029(3) 0.032(3) 0.029(3) -0.008(2) -0.008(2) 0.005(3) C5 0.033(3) 0.031(3) 0.034(3) 0.002(2) 0.003(2) 0.011(3) C6 0.044(4) 0.034(3) 0.025(3) 0.001(2) 0.007(2) 0.012(3) C7 0.040(3) 0.031(3) 0.035(3) 0.004(2) 0.003(3) 0.022(3) C8 0.039(3) 0.032(3) 0.030(3) 0.003(2) 0.009(3) 0.012(3) C9 0.034(3) 0.029(3) 0.036(3) 0.003(2) -0.004(2) 0.014(2) C10 0.034(3) 0.033(3) 0.024(3) -0.002(2) -0.007(2) 0.019(3) C11 0.034(5) 0.029(3) 0.023(4) 0.0077(17) 0.015(3) 0.017(2) C12 0.026(3) 0.028(3) 0.041(3) 0.001(2) -0.004(2) 0.010(2) C13 0.041(3) 0.030(3) 0.042(3) -0.001(3) 0.006(3) 0.011(3) C14 0.018(4) 0.025(3) 0.043(5) -0.0040(16) -0.008(3) 0.0090(19) Cu1 0.0316(6) 0.0292(4) 0.0315(5) -0.0017(2) -0.0033(4) 0.0158(3) N1 0.027(3) 0.028(3) 0.038(4) -0.0091(14) -0.018(3) 0.0134(17) N2 0.029(4) 0.040(3) 0.041(4) -0.0079(16) -0.016(3) 0.014(2) O1 0.030(2) 0.026(2) 0.042(2) 0.0033(19) -0.0059(17) 0.0061(18) O2 0.042(3) 0.036(2) 0.026(2) -0.0040(17) -0.0139(17) 0.021(2) O3 0.031(2) 0.033(2) 0.0285(19) -0.0118(17) -0.0010(17) 0.0200(18) O4 0.025(2) 0.028(2) 0.0331(19) -0.0127(16) -0.0134(16) 0.0156(17) O5 0.025(2) 0.025(2) 0.037(3) 0.0008(13) -0.0008(13) 0.005(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 C1 C2 1.393(8) . ? C1 C6 1.425(10) . ? C1 C7 1.471(9) . ? C2 O5 1.380(6) . ? C2 C3 1.408(8) . ? C3 C4 1.350(9) . ? C3 H3 0.9300 . ? C4 C5 1.424(9) . ? C4 H4 0.9300 . ? C5 C6 1.373(8) . ? C5 H5 0.9300 . ? C6 C8 1.498(8) . ? C7 O2 1.216(7) . ? C7 O1 1.242(8) . ? C8 O3 1.233(7) . ? C8 O4 1.242(8) . ? C9 N1 1.331(7) . ? C9 C10 1.378(8) . ? C9 H9 0.9300 . ? C10 C11 1.396(7) . ? C10 H10 0.9300 . ? C11 C10 1.396(7) 6_765 ? C11 C14 1.465(11) 1_545 ? C12 N2 1.336(7) . ? C12 C13 1.350(9) . ? C12 H12 0.9300 . ? C13 C14 1.372(8) . ? C13 H13 0.9300 . ? C14 C13 1.372(8) 6_765 ? C14 C11 1.465(11) 1_565 ? Cu1 O1 1.943(4) 6_765 ? Cu1 O1 1.943(4) . ? Cu1 N1 1.947(7) . ? Cu1 N2 1.986(8) . ? N1 C9 1.331(7) 6_765 ? N2 C12 1.336(7) 6_765 ? O4 H4A 0.8499 . ? O5 C2 1.380(6) 4 ? 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 C2 C1 C6 115.0(5) . . ? C2 C1 C7 118.8(6) . . ? C6 C1 C7 126.0(6) . . ? O5 C2 C1 116.8(5) . . ? O5 C2 C3 120.8(5) . . ? C1 C2 C3 122.1(5) . . ? C4 C3 C2 121.1(5) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 119.4(6) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 122.9(6) . . ? C5 C6 C8 117.2(6) . . ? C1 C6 C8 119.7(6) . . ? O2 C7 O1 125.7(6) . . ? O2 C7 C1 116.4(6) . . ? O1 C7 C1 117.9(5) . . ? O3 C8 O4 124.9(6) . . ? O3 C8 C6 119.8(6) . . ? O4 C8 C6 115.3(5) . . ? N1 C9 C10 123.9(6) . . ? N1 C9 H9 118.1 . . ? C10 C9 H9 118.1 . . ? C9 C10 C11 119.2(6) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C10 116.9(8) 6_765 . ? C10 C11 C14 121.5(4) 6_765 1_545 ? C10 C11 C14 121.5(4) . 1_545 ? N2 C12 C13 122.1(6) . . ? N2 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C12 C13 C14 120.6(6) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C13 116.6(9) 6_765 . ? C13 C14 C11 121.7(4) 6_765 1_565 ? C13 C14 C11 121.7(4) . 1_565 ? O1 Cu1 O1 178.6(3) 6_765 . ? O1 Cu1 N1 90.68(13) 6_765 . ? O1 Cu1 N1 90.68(13) . . ? O1 Cu1 N2 89.32(13) 6_765 . ? O1 Cu1 N2 89.32(13) . . ? N1 Cu1 N2 180.000(3) . . ? C9 N1 C9 116.9(7) 6_765 . ? C9 N1 Cu1 121.6(4) 6_765 . ? C9 N1 Cu1 121.6(4) . . ? C12 N2 C12 117.6(8) 6_765 . ? C12 N2 Cu1 121.2(4) 6_765 . ? C12 N2 Cu1 121.2(4) . . ? C7 O1 Cu1 124.5(4) . . ? C8 O4 H4A 126.7 . . ? C2 O5 C2 119.7(6) . 4 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4A O2 0.85 1.83 2.680(5) 179.9 6_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.478 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.099