# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Xiao-Ming Chen' _publ_contact_author_email CXM@MAIL.SYSU.EDU.CN _publ_section_title ; Syntheses, Structures and Magnetic Properties of A Family of Metal Carboxylate Polymers via In-Situ Metal/Ligand Reactions of Benzene-1,2,3-tricarboxylic Acid ; loop_ _publ_author_name 'Xiao-Ming Chen' 'Ming-Liang Tong' 'Wei Xue' 'Yue-Biao Zhang' ; Yan-Zhen Zheng ; # Attachment 'B815843F_r1.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 701820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H10 Cu3 N2 O10' _chemical_formula_weight 628.92 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 Pcan loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 6.8274(6) _cell_length_b 12.1367(11) _cell_length_c 21.808(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1807.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3866 _cell_measurement_theta_min 2.511 _cell_measurement_theta_max 25.98 _exptl_crystal_description BLOCK _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 3.573 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4087 _exptl_absorpt_correction_T_max 0.5279 _exptl_absorpt_process_details SADABS _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 '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 8903 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1772 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+12.6182P] 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 1772 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 -0.02713(9) 0.54897(4) 0.43791(3) 0.0158(2) Uani 1 1 d . . . Cu2 Cu 0.00745(11) 0.5000 0.7500 0.0149(2) Uani 1 2 d S . . O1 O -0.2637(6) 0.8440(3) 0.41476(15) 0.0239(8) Uani 1 1 d . . . O2 O -0.1888(6) 0.6686(3) 0.41166(15) 0.0236(8) Uani 1 1 d . . . O3 O -0.0785(5) 0.5815(3) 0.52380(14) 0.0189(7) Uani 1 1 d . . . O4 O 0.0073(5) 0.5178(3) 0.64186(16) 0.0182(7) Uani 1 1 d . . . O5 O 0.0020(5) 0.6481(3) 0.70999(15) 0.0184(7) Uani 1 1 d . . . N1 N -0.2902(9) 0.5000 0.7500 0.0182(12) Uani 1 2 d S . . N2 N -0.6957(8) 0.5000 0.7500 0.0173(11) Uani 1 2 d S . . C1 C -0.1202(7) 0.7728(4) 0.5050(2) 0.0177(9) Uani 1 1 d . . . C2 C -0.1000(7) 0.8801(4) 0.5267(2) 0.0191(9) Uani 1 1 d . . . H2A H -0.1263 0.9384 0.5002 0.023 Uiso 1 1 calc R . . C3 C -0.0419(8) 0.9034(4) 0.5864(2) 0.0220(10) Uani 1 1 d . . . H3A H -0.0227 0.9758 0.5991 0.026 Uiso 1 1 calc R . . C4 C -0.0132(7) 0.8165(4) 0.6267(2) 0.0174(10) Uani 1 1 d . . . H4A H 0.0173 0.8313 0.6675 0.021 Uiso 1 1 calc R . . C5 C -0.0292(7) 0.7071(4) 0.6073(2) 0.0156(9) Uani 1 1 d . . . C6 C -0.0759(7) 0.6848(4) 0.5449(2) 0.0159(9) Uani 1 1 d . . . C7 C -0.1938(7) 0.7613(4) 0.4400(2) 0.0189(9) Uani 1 1 d . . . C8 C -0.0037(6) 0.6200(4) 0.6541(2) 0.0135(9) Uani 1 1 d . . . C9 C -0.3913(7) 0.5695(4) 0.7855(2) 0.0208(10) Uani 1 1 d . . . H9A H -0.3244 0.6186 0.8108 0.025 Uiso 1 1 calc R . . C10 C -0.5948(8) 0.5695(4) 0.7853(2) 0.0216(10) Uani 1 1 d . . . H10A H -0.6619 0.6188 0.8103 0.026 Uiso 1 1 calc 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 0.0264(4) 0.0096(3) 0.0115(3) -0.00014(19) -0.0021(2) 0.0029(2) Cu2 0.0115(4) 0.0180(5) 0.0153(4) 0.0051(3) 0.000 0.000 O1 0.035(2) 0.0183(16) 0.0184(16) 0.0040(13) 0.0003(15) 0.0112(15) O2 0.037(2) 0.0167(16) 0.0168(16) -0.0032(13) -0.0095(15) 0.0119(15) O3 0.0297(19) 0.0111(15) 0.0158(16) -0.0020(13) -0.0021(14) 0.0030(14) O4 0.031(2) 0.0097(15) 0.0139(16) 0.0008(13) -0.0022(13) -0.0003(13) O5 0.0272(19) 0.0168(17) 0.0113(16) -0.0005(13) -0.0002(12) 0.0006(13) N1 0.021(3) 0.019(3) 0.015(3) 0.004(2) 0.000 0.000 N2 0.018(3) 0.018(3) 0.016(3) 0.005(2) 0.000 0.000 C1 0.016(2) 0.018(2) 0.019(2) 0.0002(17) 0.0026(18) -0.0001(18) C2 0.019(2) 0.017(2) 0.022(2) 0.0044(18) 0.0026(19) 0.0009(18) C3 0.030(3) 0.011(2) 0.025(2) -0.0032(19) 0.000(2) 0.0007(19) C4 0.022(2) 0.015(2) 0.015(2) -0.0002(18) 0.0010(17) -0.0005(17) C5 0.017(2) 0.014(2) 0.015(2) -0.0007(18) 0.0013(17) 0.0013(17) C6 0.014(2) 0.015(2) 0.018(2) -0.0002(17) 0.0033(18) -0.0001(17) C7 0.020(2) 0.018(2) 0.019(2) 0.0030(18) -0.0009(19) 0.0035(18) C8 0.011(2) 0.014(2) 0.015(2) -0.0033(19) 0.0000(15) -0.0002(15) C9 0.020(2) 0.027(2) 0.015(2) -0.0009(19) 0.0004(19) -0.004(2) C10 0.020(2) 0.025(2) 0.019(2) 0.0012(19) 0.001(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.911(3) . ? Cu1 O4 1.924(4) 5_566 ? Cu1 O3 1.930(3) 5_566 ? Cu1 O3 1.946(3) . ? Cu1 O1 2.276(4) 8_675 ? Cu1 Cu1 2.9806(11) 5_566 ? Cu2 O5 1.998(4) . ? Cu2 O5 1.998(4) 3_566 ? Cu2 N2 2.027(6) 1_655 ? Cu2 N1 2.032(6) . ? Cu2 O4 2.368(4) . ? Cu2 O4 2.368(4) 3_566 ? Cu2 C8 2.551(5) . ? Cu2 C8 2.551(5) 3_566 ? O1 C7 1.240(6) . ? O1 Cu1 2.276(3) 8_575 ? O2 C7 1.284(6) . ? O3 C6 1.336(5) . ? O3 Cu1 1.930(3) 5_566 ? O4 C8 1.271(6) . ? O4 Cu1 1.924(4) 5_566 ? O5 C8 1.267(6) . ? N1 C9 1.338(6) 3_566 ? N1 C9 1.338(6) . ? N2 C10 1.334(6) . ? N2 C10 1.334(6) 3_566 ? N2 Cu2 2.027(6) 1_455 ? C1 C2 1.393(7) . ? C1 C6 1.411(6) . ? C1 C7 1.510(6) . ? C2 C3 1.390(7) . ? C3 C4 1.387(7) . ? C4 C5 1.398(7) . ? C5 C6 1.423(6) . ? C5 C8 1.480(6) . ? C9 C10 1.390(8) . ? 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 O4 95.15(14) . 5_566 ? O2 Cu1 O3 165.58(16) . 5_566 ? O4 Cu1 O3 91.11(14) 5_566 5_566 ? O2 Cu1 O3 91.73(14) . . ? O4 Cu1 O3 165.57(14) 5_566 . ? O3 Cu1 O3 79.47(14) 5_566 . ? O2 Cu1 O1 87.50(16) . 8_675 ? O4 Cu1 O1 89.09(13) 5_566 8_675 ? O3 Cu1 O1 105.61(15) 5_566 8_675 ? O3 Cu1 O1 103.89(13) . 8_675 ? O2 Cu1 Cu1 130.30(11) . 5_566 ? O4 Cu1 Cu1 130.16(10) 5_566 5_566 ? O3 Cu1 Cu1 39.94(9) 5_566 5_566 ? O3 Cu1 Cu1 39.54(9) . 5_566 ? O1 Cu1 Cu1 109.33(9) 8_675 5_566 ? O5 Cu2 O5 177.88(19) . 3_566 ? O5 Cu2 N2 91.06(9) . 1_655 ? O5 Cu2 N2 91.06(9) 3_566 1_655 ? O5 Cu2 N1 88.94(9) . . ? O5 Cu2 N1 88.94(9) 3_566 . ? N2 Cu2 N1 180.000(3) 1_655 . ? O5 Cu2 O4 58.88(13) . . ? O5 Cu2 O4 121.12(13) 3_566 . ? N2 Cu2 O4 90.03(8) 1_655 . ? N1 Cu2 O4 89.97(8) . . ? O5 Cu2 O4 121.12(13) . 3_566 ? O5 Cu2 O4 58.88(13) 3_566 3_566 ? N2 Cu2 O4 90.03(8) 1_655 3_566 ? N1 Cu2 O4 89.97(8) . 3_566 ? O4 Cu2 O4 179.94(17) . 3_566 ? O5 Cu2 C8 29.25(14) . . ? O5 Cu2 C8 150.62(14) 3_566 . ? N2 Cu2 C8 91.71(9) 1_655 . ? N1 Cu2 C8 88.29(9) . . ? O4 Cu2 C8 29.66(13) . . ? O4 Cu2 C8 150.34(13) 3_566 . ? O5 Cu2 C8 150.62(14) . 3_566 ? O5 Cu2 C8 29.25(14) 3_566 3_566 ? N2 Cu2 C8 91.71(9) 1_655 3_566 ? N1 Cu2 C8 88.29(9) . 3_566 ? O4 Cu2 C8 150.34(13) . 3_566 ? O4 Cu2 C8 29.66(13) 3_566 3_566 ? C8 Cu2 C8 176.59(19) . 3_566 ? C7 O1 Cu1 131.9(3) . 8_575 ? C7 O2 Cu1 122.5(3) . . ? C6 O3 Cu1 128.0(3) . 5_566 ? C6 O3 Cu1 121.3(3) . . ? Cu1 O3 Cu1 100.53(14) 5_566 . ? C8 O4 Cu1 127.2(3) . 5_566 ? C8 O4 Cu2 83.1(3) . . ? Cu1 O4 Cu2 149.55(17) 5_566 . ? C8 O5 Cu2 100.3(3) . . ? C9 N1 C9 117.9(6) 3_566 . ? C9 N1 Cu2 121.1(3) 3_566 . ? C9 N1 Cu2 121.1(3) . . ? C10 N2 C10 117.8(6) . 3_566 ? C10 N2 Cu2 121.1(3) . 1_455 ? C10 N2 Cu2 121.1(3) 3_566 1_455 ? C2 C1 C6 118.5(4) . . ? C2 C1 C7 116.0(4) . . ? C6 C1 C7 125.5(4) . . ? C3 C2 C1 122.4(4) . . ? C4 C3 C2 118.7(4) . . ? C3 C4 C5 121.2(4) . . ? C4 C5 C6 119.2(4) . . ? C4 C5 C8 117.4(4) . . ? C6 C5 C8 123.3(4) . . ? O3 C6 C1 119.7(4) . . ? O3 C6 C5 120.7(4) . . ? C1 C6 C5 119.6(4) . . ? O1 C7 O2 120.4(4) . . ? O1 C7 C1 118.0(4) . . ? O2 C7 C1 121.6(4) . . ? O5 C8 O4 117.5(4) . . ? O5 C8 C5 118.4(4) . . ? O4 C8 C5 124.1(4) . . ? O5 C8 Cu2 50.4(2) . . ? O4 C8 Cu2 67.2(3) . . ? C5 C8 Cu2 167.8(3) . . ? N1 C9 C10 120.9(5) . . ? N2 C10 C9 121.2(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.430 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.129 data_6 _database_code_depnum_ccdc_archive 'CCDC 701821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H19 Cu3 N O12' _chemical_formula_weight 740.05 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8407(7) _cell_length_b 32.422(3) _cell_length_c 10.3554(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.372(2) _cell_angle_gamma 90.00 _cell_volume 2525.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5234 _cell_measurement_theta_min 2.513 _cell_measurement_theta_max 27.00 _exptl_crystal_description PLATE _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 2.577 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7473 _exptl_absorpt_correction_T_max 0.8204 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_reflns_number 14972 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5469 _reflns_number_gt 4810 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+3.9275P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment MIXED _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5469 _refine_ls_number_parameters 404 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.034 _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 0.83219(7) 0.036331(14) 0.36296(5) 0.02306(14) Uani 1 1 d . . . Cu2 Cu 0.81143(7) 0.030481(14) 0.64186(4) 0.02357(14) Uani 1 1 d . . . Cu3 Cu 0.88069(7) 0.092746(15) 0.04757(5) 0.02660(15) Uani 1 1 d . . . O1 O 0.7822(4) -0.00304(8) 0.4866(3) 0.0257(6) Uani 1 1 d . . . O2 O 0.8353(4) -0.00558(9) 0.2364(3) 0.0315(7) Uani 1 1 d . . . O3 O 0.7427(4) -0.06230(10) 0.1226(3) 0.0349(7) Uani 1 1 d . . . O4 O 0.7087(4) -0.00874(9) 0.7324(3) 0.0284(6) Uani 1 1 d . . . O5 O 0.4772(4) -0.04824(10) 0.7237(3) 0.0366(7) Uani 1 1 d . . . O6 O 0.8864(4) 0.06827(8) 0.5258(2) 0.0230(6) Uani 1 1 d . . . O7 O 0.9025(4) 0.07971(8) 0.2642(3) 0.0255(6) Uani 1 1 d . . . O8 O 1.0330(5) 0.13627(10) 0.2312(3) 0.0381(8) Uani 1 1 d . . . O9 O 0.8470(4) 0.06887(9) 0.7811(3) 0.0277(6) Uani 1 1 d . . . O10 O 0.9469(4) 0.12394(9) 0.8998(3) 0.0310(7) Uani 1 1 d . . . O1W O 1.0872(5) 0.05838(13) 0.0644(3) 0.0519(10) Uani 1 1 d D . . H1WA H 1.138(6) 0.0580(17) 0.002(4) 0.060(18) Uiso 1 1 d D . . H1WB H 1.138(6) 0.0422(12) 0.127(3) 0.041(14) Uiso 1 1 d D . . O2W O 0.7032(5) 0.04100(10) -0.0033(3) 0.0389(8) Uani 1 1 d D . . H2WA H 0.717(8) 0.0221(9) 0.055(3) 0.054(17) Uiso 1 1 d D . . H2WB H 0.693(7) 0.0308(11) -0.0799(18) 0.035(13) Uiso 1 1 d D . . N1 N 0.6793(5) 0.13163(11) 0.0335(3) 0.0288(7) Uani 1 1 d . . . C1 C 0.6900(5) -0.03813(11) 0.4553(4) 0.0207(7) Uani 1 1 d . . . C2 C 0.6043(5) -0.05628(12) 0.5441(4) 0.0235(8) Uani 1 1 d . . . C3 C 0.5204(6) -0.09421(13) 0.5105(5) 0.0315(9) Uani 1 1 d . . . H3 H 0.4661 -0.1065 0.5698 0.038 Uiso 1 1 calc R . . C4 C 0.5156(6) -0.11383(13) 0.3926(5) 0.0328(9) Uani 1 1 d . . . H4 H 0.4612 -0.1395 0.3734 0.039 Uiso 1 1 calc R . . C5 C 0.5917(6) -0.09543(12) 0.3027(4) 0.0294(9) Uani 1 1 d . . . H5 H 0.5849 -0.1086 0.2216 0.035 Uiso 1 1 calc R . . C6 C 0.6782(5) -0.05781(12) 0.3300(4) 0.0235(8) Uani 1 1 d . . . C7 C 0.5937(5) -0.03654(12) 0.6732(4) 0.0264(8) Uani 1 1 d . . . C8 C 0.7552(5) -0.04100(12) 0.2236(4) 0.0229(8) Uani 1 1 d . . . C9 C 0.9448(5) 0.10696(11) 0.5493(4) 0.0201(7) Uani 1 1 d . . . C10 C 0.9623(5) 0.12559(11) 0.6752(3) 0.0207(7) Uani 1 1 d . . . C11 C 1.0280(7) 0.16543(13) 0.6981(4) 0.0339(10) Uani 1 1 d . . . H11 H 1.0398 0.1776 0.7815 0.041 Uiso 1 1 calc R . . C12 C 1.0762(7) 0.18743(14) 0.6005(5) 0.0414(12) Uani 1 1 d . . . H12 H 1.1199 0.2142 0.6175 0.050 Uiso 1 1 calc R . . C13 C 1.0591(6) 0.16936(13) 0.4771(4) 0.0330(10) Uani 1 1 d . . . H13 H 1.0923 0.1842 0.4112 0.040 Uiso 1 1 calc R . . C14 C 0.9935(5) 0.12950(12) 0.4485(4) 0.0221(8) Uani 1 1 d . . . C15 C 0.9793(5) 0.11453(12) 0.3089(4) 0.0241(8) Uani 1 1 d . . . C16 C 0.9154(5) 0.10454(12) 0.7901(4) 0.0243(8) Uani 1 1 d . . . C17 C 0.5316(6) 0.12159(13) 0.0668(4) 0.0316(9) Uani 1 1 d . . . H17 H 0.5204 0.0949 0.0960 0.038 Uiso 1 1 calc R . . C18 C 0.3953(6) 0.14916(14) 0.0599(5) 0.0338(10) Uani 1 1 d . . . H18 H 0.2953 0.1410 0.0847 0.041 Uiso 1 1 calc R . . C19 C 0.4077(6) 0.18938(13) 0.0155(4) 0.0306(9) Uani 1 1 d . . . C20 C 0.5624(7) 0.19913(14) -0.0184(5) 0.0392(11) Uani 1 1 d . . . H20 H 0.5774 0.2256 -0.0482 0.047 Uiso 1 1 calc R . . C21 C 0.6921(7) 0.17035(14) -0.0084(5) 0.0385(11) Uani 1 1 d . . . H21 H 0.7940 0.1779 -0.0317 0.046 Uiso 1 1 calc R . . C22 C 0.2657(6) 0.22060(14) 0.0057(5) 0.0362(10) Uani 1 1 d . . . C23 C 0.1592(8) 0.21960(18) 0.0927(6) 0.0534(14) Uani 1 1 d . . . H23 H 0.1746 0.1990 0.1573 0.064 Uiso 1 1 calc R . . C24 C 0.0312(8) 0.2493(2) 0.0825(8) 0.072(2) Uani 1 1 d . . . H24 H -0.0376 0.2489 0.1424 0.087 Uiso 1 1 calc R . . C25 C 0.0026(9) 0.2793(2) -0.0134(9) 0.078(2) Uani 1 1 d . . . H25 H -0.0849 0.2991 -0.0187 0.094 Uiso 1 1 calc R . . C26 C 0.1038(9) 0.28019(18) -0.1024(7) 0.0680(18) Uani 1 1 d . . . H26 H 0.0830 0.3001 -0.1697 0.082 Uiso 1 1 calc R . . C27 C 0.2361(7) 0.25135(16) -0.0913(6) 0.0478(12) Uani 1 1 d . . . H27 H 0.3069 0.2525 -0.1498 0.057 Uiso 1 1 calc 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 0.0327(3) 0.0216(2) 0.0190(2) -0.00092(17) 0.0138(2) -0.00421(19) Cu2 0.0305(3) 0.0256(3) 0.0171(2) 0.00254(17) 0.01074(19) -0.00288(19) Cu3 0.0282(3) 0.0311(3) 0.0216(3) 0.00387(19) 0.0089(2) 0.0037(2) O1 0.0361(17) 0.0253(14) 0.0199(13) 0.0005(10) 0.0148(12) -0.0068(12) O2 0.0472(19) 0.0258(14) 0.0283(15) -0.0064(12) 0.0221(14) -0.0048(13) O3 0.0389(18) 0.0418(17) 0.0278(15) -0.0126(13) 0.0156(13) -0.0104(14) O4 0.0340(17) 0.0348(15) 0.0184(13) 0.0070(11) 0.0106(12) -0.0063(12) O5 0.0288(16) 0.056(2) 0.0279(16) 0.0088(14) 0.0124(13) -0.0072(14) O6 0.0343(16) 0.0232(13) 0.0143(12) 0.0002(10) 0.0114(11) -0.0029(11) O7 0.0339(16) 0.0246(13) 0.0211(13) -0.0003(11) 0.0128(12) -0.0072(12) O8 0.056(2) 0.0398(18) 0.0236(15) 0.0017(13) 0.0185(14) -0.0155(15) O9 0.0367(17) 0.0319(15) 0.0162(12) 0.0004(11) 0.0105(11) -0.0033(12) O10 0.0466(19) 0.0305(15) 0.0178(13) -0.0026(11) 0.0120(12) 0.0075(13) O1W 0.052(2) 0.081(3) 0.0296(18) 0.0273(18) 0.0232(16) 0.039(2) O2W 0.059(2) 0.0324(17) 0.0286(17) -0.0010(14) 0.0182(16) 0.0001(15) N1 0.0288(19) 0.0281(17) 0.0288(18) -0.0006(14) 0.0072(14) -0.0015(14) C1 0.0143(17) 0.0237(18) 0.0229(18) 0.0054(14) 0.0032(14) 0.0009(14) C2 0.0167(18) 0.0279(19) 0.0251(19) 0.0078(15) 0.0047(15) 0.0015(15) C3 0.024(2) 0.032(2) 0.038(2) 0.0118(18) 0.0084(18) -0.0018(17) C4 0.027(2) 0.029(2) 0.041(2) 0.0015(18) 0.0063(18) -0.0076(17) C5 0.027(2) 0.028(2) 0.029(2) -0.0025(16) 0.0015(17) 0.0007(16) C6 0.0210(19) 0.0254(19) 0.0248(19) 0.0035(15) 0.0078(15) 0.0031(15) C7 0.026(2) 0.032(2) 0.0210(18) 0.0126(16) 0.0053(16) 0.0067(16) C8 0.0201(19) 0.0253(19) 0.0244(19) 0.0016(15) 0.0082(15) 0.0034(15) C9 0.0192(18) 0.0233(18) 0.0179(17) 0.0036(14) 0.0056(14) 0.0032(14) C10 0.025(2) 0.0241(18) 0.0122(16) 0.0024(14) 0.0040(14) 0.0026(15) C11 0.051(3) 0.032(2) 0.0188(19) -0.0078(16) 0.0104(18) -0.001(2) C12 0.063(3) 0.029(2) 0.032(2) -0.0080(18) 0.014(2) -0.016(2) C13 0.044(3) 0.031(2) 0.024(2) 0.0029(17) 0.0108(18) -0.0096(19) C14 0.024(2) 0.0252(18) 0.0162(17) -0.0008(14) 0.0043(14) -0.0029(15) C15 0.023(2) 0.032(2) 0.0189(18) 0.0034(15) 0.0090(15) 0.0002(16) C16 0.027(2) 0.029(2) 0.0175(18) 0.0041(15) 0.0070(15) 0.0112(16) C17 0.033(2) 0.030(2) 0.032(2) 0.0036(17) 0.0099(18) -0.0039(17) C18 0.031(2) 0.034(2) 0.039(2) 0.0003(18) 0.0122(19) -0.0063(18) C19 0.033(2) 0.031(2) 0.028(2) -0.0073(17) 0.0085(17) -0.0022(17) C20 0.047(3) 0.024(2) 0.055(3) 0.005(2) 0.029(2) -0.0020(19) C21 0.044(3) 0.029(2) 0.052(3) -0.001(2) 0.030(2) -0.0049(19) C22 0.030(2) 0.032(2) 0.044(3) -0.0126(19) 0.0066(19) -0.0028(18) C23 0.048(3) 0.053(3) 0.064(4) -0.008(3) 0.023(3) -0.002(3) C24 0.044(3) 0.071(4) 0.115(6) -0.022(4) 0.043(4) 0.002(3) C25 0.043(4) 0.055(4) 0.130(7) -0.022(4) 0.011(4) 0.011(3) C26 0.062(4) 0.043(3) 0.082(5) -0.004(3) -0.008(3) 0.012(3) C27 0.048(3) 0.041(3) 0.052(3) -0.001(2) 0.010(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.892(3) . ? Cu1 O7 1.909(3) . ? Cu1 O6 1.922(3) . ? Cu1 O1 1.925(2) . ? Cu1 O5 2.369(3) 3_656 ? Cu1 Cu2 2.9443(7) . ? Cu2 O9 1.865(3) . ? Cu2 O4 1.890(3) . ? Cu2 O1 1.900(3) . ? Cu2 O6 1.921(2) . ? Cu3 O1W 1.932(3) . ? Cu3 N1 1.994(4) . ? Cu3 O10 2.020(3) 1_554 ? Cu3 O2W 2.148(3) . ? Cu3 O7 2.241(3) . ? Cu3 O8 2.399(3) . ? O1 C1 1.338(4) . ? O2 C8 1.298(5) . ? O3 C8 1.234(5) . ? O4 C7 1.300(5) . ? O5 C7 1.233(5) . ? O5 Cu1 2.369(3) 3_656 ? O6 C9 1.334(5) . ? O7 C15 1.301(5) . ? O8 C15 1.229(5) . ? O9 C16 1.267(5) . ? O10 C16 1.261(5) . ? O10 Cu3 2.020(3) 1_556 ? O1W H1WA 0.847(10) . ? O1W H1WB 0.843(10) . ? O2W H2WA 0.846(10) . ? O2W H2WB 0.843(10) . ? N1 C17 1.338(5) . ? N1 C21 1.341(6) . ? C1 C2 1.411(5) . ? C1 C6 1.425(5) . ? C2 C3 1.392(6) . ? C2 C7 1.506(6) . ? C3 C4 1.368(6) . ? C3 H3 0.9300 . ? C4 C5 1.376(6) . ? C4 H4 0.9300 . ? C5 C6 1.386(6) . ? C5 H5 0.9300 . ? C6 C8 1.501(5) . ? C9 C10 1.408(5) . ? C9 C14 1.412(5) . ? C10 C11 1.386(6) . ? C10 C16 1.504(5) . ? C11 C12 1.374(6) . ? C11 H11 0.9300 . ? C12 C13 1.377(6) . ? C12 H12 0.9300 . ? C13 C14 1.392(5) . ? C13 H13 0.9300 . ? C14 C15 1.499(5) . ? C17 C18 1.380(6) . ? C17 H17 0.9300 . ? C18 C19 1.395(6) . ? C18 H18 0.9300 . ? C19 C20 1.391(6) . ? C19 C22 1.487(6) . ? C20 C21 1.362(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C27 1.387(7) . ? C22 C23 1.391(7) . ? C23 C24 1.374(8) . ? C23 H23 0.9300 . ? C24 C25 1.363(10) . ? C24 H24 0.9300 . ? C25 C26 1.376(10) . ? C25 H25 0.9300 . ? C26 C27 1.377(8) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O7 95.50(12) . . ? O2 Cu1 O6 162.10(13) . . ? O7 Cu1 O6 92.71(11) . . ? O2 Cu1 O1 91.69(12) . . ? O7 Cu1 O1 171.26(11) . . ? O6 Cu1 O1 79.02(11) . . ? O2 Cu1 O5 93.82(13) . 3_656 ? O7 Cu1 O5 95.53(11) . 3_656 ? O6 Cu1 O5 101.20(12) . 3_656 ? O1 Cu1 O5 88.93(11) . 3_656 ? O2 Cu1 Cu2 130.39(9) . . ? O7 Cu1 Cu2 132.61(8) . . ? O6 Cu1 Cu2 39.97(7) . . ? O1 Cu1 Cu2 39.36(8) . . ? O5 Cu1 Cu2 92.76(7) 3_656 . ? O9 Cu2 O4 93.29(12) . . ? O9 Cu2 O1 172.64(11) . . ? O4 Cu2 O1 93.91(12) . . ? O9 Cu2 O6 93.00(11) . . ? O4 Cu2 O6 171.17(12) . . ? O1 Cu2 O6 79.67(11) . . ? O9 Cu2 Cu1 132.65(8) . . ? O4 Cu2 Cu1 132.78(9) . . ? O1 Cu2 Cu1 39.99(8) . . ? O6 Cu2 Cu1 39.99(8) . . ? O1W Cu3 N1 175.93(17) . . ? O1W Cu3 O10 88.22(13) . 1_554 ? N1 Cu3 O10 89.75(13) . 1_554 ? O1W Cu3 O2W 92.30(17) . . ? N1 Cu3 O2W 91.77(14) . . ? O10 Cu3 O2W 119.50(12) 1_554 . ? O1W Cu3 O7 88.60(12) . . ? N1 Cu3 O7 91.59(12) . . ? O10 Cu3 O7 152.75(11) 1_554 . ? O2W Cu3 O7 87.67(11) . . ? O1W Cu3 O8 92.91(16) . . ? N1 Cu3 O8 83.85(13) . . ? O10 Cu3 O8 97.42(11) 1_554 . ? O2W Cu3 O8 142.85(11) . . ? O7 Cu3 O8 55.73(9) . . ? C1 O1 Cu2 128.3(2) . . ? C1 O1 Cu1 126.9(2) . . ? Cu2 O1 Cu1 100.66(12) . . ? C8 O2 Cu1 127.3(2) . . ? C7 O4 Cu2 124.7(2) . . ? C7 O5 Cu1 126.2(3) . 3_656 ? C9 O6 Cu2 129.4(2) . . ? C9 O6 Cu1 130.3(2) . . ? Cu2 O6 Cu1 100.04(12) . . ? C15 O7 Cu1 128.5(2) . . ? C15 O7 Cu3 95.1(2) . . ? Cu1 O7 Cu3 136.30(14) . . ? C15 O8 Cu3 89.7(2) . . ? C16 O9 Cu2 129.3(2) . . ? C16 O10 Cu3 114.0(3) . 1_556 ? Cu3 O1W H1WA 120(3) . . ? Cu3 O1W H1WB 129(3) . . ? H1WA O1W H1WB 110.8(18) . . ? Cu3 O2W H2WA 117(4) . . ? Cu3 O2W H2WB 115(3) . . ? H2WA O2W H2WB 110.5(18) . . ? C17 N1 C21 117.4(4) . . ? C17 N1 Cu3 123.5(3) . . ? C21 N1 Cu3 119.0(3) . . ? O1 C1 C2 121.4(3) . . ? O1 C1 C6 119.6(3) . . ? C2 C1 C6 119.1(3) . . ? C3 C2 C1 118.9(4) . . ? C3 C2 C7 117.2(3) . . ? C1 C2 C7 123.8(4) . . ? C4 C3 C2 121.8(4) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 121.6(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 118.8(3) . . ? C5 C6 C8 116.4(4) . . ? C1 C6 C8 124.8(3) . . ? O5 C7 O4 120.8(4) . . ? O5 C7 C2 118.6(4) . . ? O4 C7 C2 120.6(3) . . ? O3 C8 O2 120.2(3) . . ? O3 C8 C6 117.9(4) . . ? O2 C8 C6 122.0(3) . . ? O6 C9 C10 120.8(3) . . ? O6 C9 C14 120.1(3) . . ? C10 C9 C14 119.1(3) . . ? C11 C10 C9 119.5(3) . . ? C11 C10 C16 116.7(3) . . ? C9 C10 C16 123.8(3) . . ? C12 C11 C10 121.6(4) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 119.1(4) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 121.8(4) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C13 C14 C9 118.9(3) . . ? C13 C14 C15 115.4(3) . . ? C9 C14 C15 125.7(3) . . ? O8 C15 O7 118.3(3) . . ? O8 C15 C14 119.9(4) . . ? O7 C15 C14 121.7(3) . . ? O10 C16 O9 119.5(3) . . ? O10 C16 C10 117.2(4) . . ? O9 C16 C10 123.3(3) . . ? N1 C17 C18 122.9(4) . . ? N1 C17 H17 118.6 . . ? C18 C17 H17 118.6 . . ? C17 C18 C19 119.9(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 116.3(4) . . ? C20 C19 C22 121.2(4) . . ? C18 C19 C22 122.6(4) . . ? C21 C20 C19 120.7(4) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? N1 C21 C20 122.9(4) . . ? N1 C21 H21 118.6 . . ? C20 C21 H21 118.6 . . ? C27 C22 C23 118.5(5) . . ? C27 C22 C19 120.5(4) . . ? C23 C22 C19 121.0(5) . . ? C24 C23 C22 119.5(6) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C25 C24 C23 121.5(6) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C24 C25 C26 119.7(6) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C27 119.6(6) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C26 C27 C22 121.1(6) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? 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 O1W H1WA O3 0.847(10) 1.802(13) 2.645(4) 174(6) 3_755 O1W H1WB O4 0.843(10) 1.937(14) 2.772(4) 170(5) 3_756 O2W H2WA O2 0.846(10) 2.05(2) 2.840(4) 155(5) . O2W H2WB O4 0.843(10) 2.359(15) 3.188(4) 167(4) 1_554 O2W H2WB O9 0.843(10) 2.46(4) 2.915(4) 115(3) 1_554 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.573 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.109 data_7 _database_code_depnum_ccdc_archive 'CCDC 701822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 Cu N2 O4' _chemical_formula_weight 538.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting TRICLINIC _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1928(10) _cell_length_b 10.9107(10) _cell_length_c 12.9882(12) _cell_angle_alpha 105.562(2) _cell_angle_beta 111.228(2) _cell_angle_gamma 100.438(2) _cell_volume 1233.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1089 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 25.00 _exptl_crystal_description PLATE _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 0.926 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8084 _exptl_absorpt_correction_T_max 0.9552 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_reflns_number 8927 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4298 _reflns_number_gt 3000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0931P)^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_number_reflns 4298 _refine_ls_number_parameters 334 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1784 _refine_ls_wR_factor_gt 0.1603 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.107 _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 0.91219(7) 0.66456(7) 0.56655(6) 0.0314(3) Uani 1 1 d . . . O1 O 0.7287(4) 0.6773(4) 0.5821(3) 0.0373(9) Uani 1 1 d . . . O2 O 0.8604(4) 0.8924(4) 0.6657(4) 0.0520(12) Uani 1 1 d . . . O3 O 0.2059(4) 0.5548(4) 0.5484(4) 0.0479(11) Uani 1 1 d . . . O4 O 0.1084(4) 0.7203(4) 0.5748(4) 0.0457(11) Uani 1 1 d . . . N1 N 1.0012(5) 0.6376(5) 0.7208(4) 0.0355(11) Uani 1 1 d . . . N2 N 0.8384(5) 0.7155(4) 0.4202(4) 0.0344(11) Uani 1 1 d . . . C1 C 0.6048(6) 0.8356(6) 0.6212(5) 0.0323(13) Uani 1 1 d . . . C2 C 0.4759(5) 0.7394(5) 0.5965(4) 0.0279(12) Uani 1 1 d . . . H2 H 0.4725 0.6502 0.5795 0.034 Uiso 1 1 calc R . . C3 C 0.3529(5) 0.7760(5) 0.5972(4) 0.0298(12) Uani 1 1 d . . . C4 C 0.3607(6) 0.9102(6) 0.6226(5) 0.0385(14) Uani 1 1 d . . . H4 H 0.2795 0.9366 0.6245 0.046 Uiso 1 1 calc R . . C5 C 0.4872(7) 1.0042(6) 0.6448(6) 0.0479(17) Uani 1 1 d . . . H5 H 0.4909 1.0934 0.6601 0.057 Uiso 1 1 calc R . . C6 C 0.6061(6) 0.9665(6) 0.6442(5) 0.0419(15) Uani 1 1 d . . . H6 H 0.6914 1.0309 0.6599 0.050 Uiso 1 1 calc R . . C7 C 0.7425(6) 0.7998(6) 0.6239(5) 0.0350(13) Uani 1 1 d . . . C8 C 0.2123(6) 0.6727(6) 0.5712(5) 0.0305(13) Uani 1 1 d . . . C9 C 1.0215(10) 0.7227(8) 0.8217(7) 0.082(3) Uani 1 1 d U . . H9 H 0.9902 0.7975 0.8207 0.098 Uiso 1 1 calc R . . C10 C 1.0858(10) 0.7092(8) 0.9289(7) 0.088(3) Uani 1 1 d U . . H10 H 1.0978 0.7751 0.9972 0.105 Uiso 1 1 calc R . . C11 C 1.1326(6) 0.6017(6) 0.9381(5) 0.0419(15) Uani 1 1 d . . . C12 C 1.1105(9) 0.5142(7) 0.8325(6) 0.062(2) Uani 1 1 d . . . H12 H 1.1396 0.4379 0.8303 0.074 Uiso 1 1 calc R . . C13 C 1.0467(8) 0.5353(7) 0.7292(6) 0.061(2) Uani 1 1 d . . . H13 H 1.0348 0.4718 0.6597 0.073 Uiso 1 1 calc R . . C14 C 1.1969(6) 0.5815(6) 1.0524(5) 0.0409(15) Uani 1 1 d . . . C15 C 1.2172(8) 0.6710(7) 1.1572(6) 0.0589(19) Uani 1 1 d . . . H15 H 1.1914 0.7485 1.1574 0.071 Uiso 1 1 calc R . . C16 C 1.2740(8) 0.6508(8) 1.2617(6) 0.064(2) Uani 1 1 d . . . H16 H 1.2874 0.7155 1.3312 0.077 Uiso 1 1 calc R . . C17 C 1.3104(8) 0.5411(8) 1.2663(6) 0.061(2) Uani 1 1 d . . . H17 H 1.3452 0.5259 1.3370 0.073 Uiso 1 1 calc R . . C18 C 1.2951(10) 0.4525(9) 1.1645(7) 0.086(3) Uani 1 1 d . . . H18 H 1.3229 0.3761 1.1658 0.103 Uiso 1 1 calc R . . C19 C 1.2396(10) 0.4720(8) 1.0592(7) 0.078(3) Uani 1 1 d . . . H19 H 1.2310 0.4087 0.9909 0.094 Uiso 1 1 calc R . . C20 C 0.7015(7) 0.6545(6) 0.3333(6) 0.0475(16) Uani 1 1 d . . . H20 H 0.6392 0.5862 0.3397 0.057 Uiso 1 1 calc R . . C21 C 0.6489(7) 0.6883(7) 0.2351(6) 0.0513(17) Uani 1 1 d . . . H21 H 0.5530 0.6423 0.1765 0.062 Uiso 1 1 calc R . . C22 C 0.7367(7) 0.7900(6) 0.2221(5) 0.0394(15) Uani 1 1 d . . . C23 C 0.8775(7) 0.8557(6) 0.3151(6) 0.0494(17) Uani 1 1 d . . . H23 H 0.9407 0.9269 0.3128 0.059 Uiso 1 1 calc R . . C24 C 0.9229(7) 0.8154(6) 0.4098(5) 0.0451(16) Uani 1 1 d . . . H24 H 1.0179 0.8602 0.4701 0.054 Uiso 1 1 calc R . . C25 C 0.6881(8) 0.8275(6) 0.1172(6) 0.0507(17) Uani 1 1 d . . . C26 C 0.5480(10) 0.7841(10) 0.0364(8) 0.090(3) Uani 1 1 d U . . H26 H 0.4775 0.7298 0.0482 0.108 Uiso 1 1 calc R . . C27 C 0.5021(12) 0.8160(11) -0.0645(9) 0.109(3) Uani 1 1 d U . . H27 H 0.4021 0.7849 -0.1166 0.130 Uiso 1 1 calc R . . C28 C 0.5947(11) 0.8879(9) -0.0881(7) 0.082(3) Uani 1 1 d . . . H28 H 0.5610 0.9165 -0.1514 0.099 Uiso 1 1 calc R . . C29 C 0.7457(13) 0.9218(10) -0.0171(9) 0.113(3) Uani 1 1 d U . . H29 H 0.8143 0.9621 -0.0391 0.136 Uiso 1 1 calc R . . C30 C 0.7944(12) 0.8943(10) 0.0897(9) 0.107(3) Uani 1 1 d U . . H30 H 0.8948 0.9202 0.1400 0.129 Uiso 1 1 calc 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 0.0213(4) 0.0396(4) 0.0396(4) 0.0184(3) 0.0157(3) 0.0122(3) O1 0.028(2) 0.043(3) 0.053(3) 0.021(2) 0.0242(19) 0.0183(19) O2 0.024(2) 0.047(3) 0.077(3) 0.018(2) 0.021(2) 0.003(2) O3 0.034(2) 0.036(3) 0.065(3) 0.013(2) 0.020(2) 0.004(2) O4 0.026(2) 0.051(3) 0.079(3) 0.036(2) 0.032(2) 0.019(2) N1 0.031(3) 0.037(3) 0.038(3) 0.012(2) 0.016(2) 0.009(2) N2 0.030(3) 0.034(3) 0.043(3) 0.018(2) 0.016(2) 0.011(2) C1 0.027(3) 0.037(3) 0.033(3) 0.013(3) 0.014(3) 0.010(3) C2 0.024(3) 0.026(3) 0.033(3) 0.011(2) 0.011(2) 0.008(2) C3 0.021(3) 0.039(3) 0.029(3) 0.013(3) 0.009(2) 0.009(2) C4 0.033(3) 0.037(4) 0.052(4) 0.017(3) 0.020(3) 0.020(3) C5 0.039(4) 0.030(3) 0.076(5) 0.022(3) 0.024(3) 0.014(3) C6 0.028(3) 0.037(4) 0.062(4) 0.020(3) 0.021(3) 0.006(3) C7 0.029(3) 0.042(4) 0.037(3) 0.017(3) 0.014(3) 0.011(3) C8 0.026(3) 0.040(4) 0.028(3) 0.015(3) 0.011(2) 0.011(3) C9 0.106(5) 0.065(4) 0.067(4) 0.028(3) 0.016(3) 0.046(4) C10 0.115(5) 0.072(4) 0.064(4) 0.021(3) 0.019(3) 0.049(4) C11 0.032(3) 0.039(4) 0.046(4) 0.017(3) 0.009(3) 0.007(3) C12 0.094(6) 0.066(5) 0.044(4) 0.027(4) 0.029(4) 0.057(5) C13 0.092(6) 0.073(5) 0.043(4) 0.026(4) 0.036(4) 0.058(5) C14 0.031(3) 0.043(4) 0.039(4) 0.016(3) 0.008(3) 0.001(3) C15 0.076(5) 0.052(4) 0.048(4) 0.019(4) 0.026(4) 0.019(4) C16 0.077(5) 0.069(5) 0.040(4) 0.022(4) 0.020(4) 0.014(4) C17 0.050(4) 0.069(5) 0.048(4) 0.031(4) 0.007(3) -0.002(4) C18 0.120(8) 0.069(6) 0.063(6) 0.037(5) 0.018(5) 0.044(5) C19 0.113(7) 0.063(5) 0.050(5) 0.023(4) 0.017(5) 0.044(5) C20 0.033(4) 0.048(4) 0.055(4) 0.022(3) 0.014(3) 0.006(3) C21 0.039(4) 0.055(4) 0.049(4) 0.021(3) 0.008(3) 0.010(3) C22 0.049(4) 0.037(4) 0.034(3) 0.012(3) 0.018(3) 0.017(3) C23 0.049(4) 0.041(4) 0.060(4) 0.030(3) 0.021(4) 0.007(3) C24 0.036(4) 0.045(4) 0.048(4) 0.020(3) 0.011(3) 0.008(3) C25 0.061(5) 0.043(4) 0.040(4) 0.015(3) 0.014(3) 0.015(3) C26 0.080(4) 0.114(5) 0.086(4) 0.057(4) 0.034(3) 0.020(4) C27 0.099(5) 0.128(5) 0.098(5) 0.056(4) 0.033(4) 0.028(4) C28 0.103(7) 0.074(6) 0.052(5) 0.037(4) 0.008(5) 0.022(5) C29 0.127(6) 0.108(5) 0.103(5) 0.059(4) 0.044(4) 0.012(4) C30 0.115(5) 0.103(5) 0.095(5) 0.054(4) 0.033(4) 0.012(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 O4 1.937(4) 1_655 ? Cu1 O1 1.978(4) . ? Cu1 N1 2.005(5) . ? Cu1 N2 2.042(4) . ? Cu1 O3 2.268(4) 2_666 ? O1 C7 1.261(7) . ? O2 C7 1.247(6) . ? O3 C8 1.224(6) . ? O3 Cu1 2.268(4) 2_666 ? O4 C8 1.270(6) . ? O4 Cu1 1.937(4) 1_455 ? N1 C13 1.300(8) . ? N1 C9 1.306(9) . ? N2 C24 1.331(7) . ? N2 C20 1.335(7) . ? C1 C6 1.375(8) . ? C1 C2 1.394(7) . ? C1 C7 1.515(7) . ? C2 C3 1.386(7) . ? C3 C4 1.392(7) . ? C3 C8 1.516(7) . ? C4 C5 1.375(8) . ? C5 C6 1.351(8) . ? C9 C10 1.369(10) . ? C10 C11 1.362(9) . ? C11 C12 1.357(9) . ? C11 C14 1.485(8) . ? C12 C13 1.365(8) . ? C14 C19 1.357(9) . ? C14 C15 1.363(9) . ? C15 C16 1.365(9) . ? C16 C17 1.325(10) . ? C17 C18 1.348(10) . ? C18 C19 1.368(10) . ? C20 C21 1.371(8) . ? C21 C22 1.382(8) . ? C22 C23 1.393(8) . ? C22 C25 1.467(8) . ? C23 C24 1.368(8) . ? C25 C26 1.330(10) . ? C25 C30 1.403(11) . ? C26 C27 1.384(11) . ? C27 C28 1.292(12) . ? C28 C29 1.392(12) . ? C29 C30 1.427(12) . ? 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 O1 159.62(17) 1_655 . ? O4 Cu1 N1 89.24(18) 1_655 . ? O1 Cu1 N1 93.22(17) . . ? O4 Cu1 N2 86.93(17) 1_655 . ? O1 Cu1 N2 88.38(17) . . ? N1 Cu1 N2 173.01(19) . . ? O4 Cu1 O3 111.11(16) 1_655 2_666 ? O1 Cu1 O3 88.73(16) . 2_666 ? N1 Cu1 O3 96.53(17) . 2_666 ? N2 Cu1 O3 90.30(17) . 2_666 ? C7 O1 Cu1 107.4(3) . . ? C8 O3 Cu1 150.7(4) . 2_666 ? C8 O4 Cu1 140.0(4) . 1_455 ? C13 N1 C9 114.2(6) . . ? C13 N1 Cu1 122.8(4) . . ? C9 N1 Cu1 122.9(5) . . ? C24 N2 C20 116.9(5) . . ? C24 N2 Cu1 121.2(4) . . ? C20 N2 Cu1 121.8(4) . . ? C6 C1 C2 118.7(5) . . ? C6 C1 C7 119.4(5) . . ? C2 C1 C7 121.9(5) . . ? C3 C2 C1 120.4(5) . . ? C2 C3 C4 118.7(5) . . ? C2 C3 C8 121.0(5) . . ? C4 C3 C8 120.3(5) . . ? C5 C4 C3 120.6(5) . . ? C6 C5 C4 119.7(5) . . ? C5 C6 C1 121.9(5) . . ? O2 C7 O1 124.6(5) . . ? O2 C7 C1 118.4(5) . . ? O1 C7 C1 117.1(5) . . ? O3 C8 O4 125.7(5) . . ? O3 C8 C3 120.0(5) . . ? O4 C8 C3 114.3(5) . . ? N1 C9 C10 124.4(7) . . ? C11 C10 C9 121.6(8) . . ? C12 C11 C10 113.2(6) . . ? C12 C11 C14 123.9(6) . . ? C10 C11 C14 122.8(6) . . ? C11 C12 C13 121.7(6) . . ? N1 C13 C12 124.9(6) . . ? C19 C14 C15 115.5(6) . . ? C19 C14 C11 121.9(6) . . ? C15 C14 C11 122.6(6) . . ? C14 C15 C16 122.4(7) . . ? C17 C16 C15 121.4(7) . . ? C16 C17 C18 117.5(7) . . ? C17 C18 C19 121.7(8) . . ? C14 C19 C18 121.5(7) . . ? N2 C20 C21 122.8(6) . . ? C20 C21 C22 120.8(6) . . ? C21 C22 C23 115.9(5) . . ? C21 C22 C25 123.2(6) . . ? C23 C22 C25 120.9(6) . . ? C24 C23 C22 120.0(6) . . ? N2 C24 C23 123.6(6) . . ? C26 C25 C30 117.0(8) . . ? C26 C25 C22 122.8(7) . . ? C30 C25 C22 119.4(7) . . ? C25 C26 C27 123.1(9) . . ? C28 C27 C26 121.7(10) . . ? C27 C28 C29 119.0(9) . . ? C28 C29 C30 119.5(9) . . ? C25 C30 C29 118.7(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.923 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.102 data_9 _database_code_depnum_ccdc_archive 'CCDC 701824' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 Co N2 O5' _chemical_formula_weight 421.26 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7668(11) _cell_length_b 9.4601(13) _cell_length_c 12.5416(17) _cell_angle_alpha 73.368(2) _cell_angle_beta 84.736(2) _cell_angle_gamma 71.367(2) _cell_volume 836.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3370 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 26.00 _exptl_crystal_description BLOCK _exptl_crystal_colour RED _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 430 _exptl_absorpt_coefficient_mu 1.064 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6518 _exptl_absorpt_correction_T_max 0.8671 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6379 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3257 _reflns_number_gt 2949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.6539P] 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 3257 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Co1 Co 0.03807(5) 0.08408(4) 0.80564(3) 0.02575(14) Uani 1 1 d . . . O1 O 0.2852(3) -0.0127(2) 0.90764(17) 0.0336(5) Uani 1 1 d . . . O2 O 0.2523(3) -0.1220(2) 0.78313(18) 0.0423(5) Uani 1 1 d . . . O3 O 0.9111(3) -0.7491(2) 0.88334(16) 0.0343(5) Uani 1 1 d . . . O4 O 0.6831(3) -0.6294(3) 0.76327(19) 0.0461(6) Uani 1 1 d . . . N1 N 0.1511(3) 0.2252(3) 0.67399(19) 0.0297(5) Uani 1 1 d . . . N2 N -0.1105(3) 0.0985(3) 0.66963(19) 0.0275(5) Uani 1 1 d . . . O1W O -0.0861(3) -0.0688(2) 0.91657(16) 0.0349(5) Uani 1 1 d . . . H1WA H -0.1637 -0.0363 0.9718 0.042 Uiso 1 1 calc R . . H1WB H -0.0631 -0.1688 0.9103 0.042 Uiso 1 1 calc R . . C1 C 0.7672(4) -0.6374(3) 0.8432(2) 0.0275(6) Uani 1 1 d . . . C2 C 0.5047(4) -0.2567(3) 0.9060(2) 0.0263(6) Uani 1 1 d . . . C3 C 0.5608(4) -0.3786(3) 0.8572(2) 0.0271(6) Uani 1 1 d . . . H3A H 0.4997 -0.3734 0.7951 0.033 Uiso 1 1 calc R . . C4 C 0.3396(4) -0.1233(3) 0.8628(2) 0.0294(6) Uani 1 1 d . . . C5 C 0.7072(4) -0.5084(3) 0.9001(2) 0.0260(6) Uani 1 1 d . . . C6 C -0.0620(4) 0.1809(3) 0.5715(2) 0.0270(6) Uani 1 1 d . . . C7 C 0.0787(4) 0.2495(3) 0.5730(2) 0.0285(6) Uani 1 1 d . . . C8 C 0.7951(4) -0.5148(3) 0.9938(2) 0.0324(6) Uani 1 1 d . . . H8A H 0.8919 -0.6017 1.0243 0.039 Uiso 1 1 calc R . . C9 C -0.1384(4) 0.1994(3) 0.4695(2) 0.0321(6) Uani 1 1 d . . . C10 C 0.7403(4) -0.3929(4) 1.0422(3) 0.0367(7) Uani 1 1 d . . . H10A H 0.8010 -0.3980 1.1045 0.044 Uiso 1 1 calc R . . C11 C 0.2841(4) 0.2844(4) 0.6771(3) 0.0363(7) Uani 1 1 d . . . H11A H 0.3360 0.2671 0.7454 0.044 Uiso 1 1 calc R . . C12 C 0.5950(4) -0.2631(3) 0.9983(2) 0.0313(6) Uani 1 1 d . . . H12A H 0.5586 -0.1811 1.0306 0.038 Uiso 1 1 calc R . . C13 C 0.0558(5) 0.3495(4) 0.3715(3) 0.0428(8) Uani 1 1 d . . . H13A H 0.0948 0.4050 0.3051 0.051 Uiso 1 1 calc R . . C14 C -0.2370(4) 0.0326(4) 0.6700(3) 0.0347(6) Uani 1 1 d . . . H14A H -0.2715 -0.0236 0.7376 0.042 Uiso 1 1 calc R . . C15 C 0.1373(4) 0.3334(3) 0.4735(2) 0.0348(7) Uani 1 1 d . . . C16 C -0.2727(4) 0.1269(4) 0.4728(3) 0.0389(7) Uani 1 1 d . . . H16A H -0.3280 0.1355 0.4076 0.047 Uiso 1 1 calc R . . C17 C -0.0762(5) 0.2863(4) 0.3688(2) 0.0405(7) Uani 1 1 d . . . H17A H -0.1272 0.2993 0.3011 0.049 Uiso 1 1 calc R . . C18 C -0.3207(4) 0.0439(4) 0.5731(3) 0.0396(7) Uani 1 1 d . . . H18A H -0.4087 -0.0048 0.5765 0.048 Uiso 1 1 calc R . . C19 C 0.3485(5) 0.3711(4) 0.5821(3) 0.0431(8) Uani 1 1 d . . . H19A H 0.4403 0.4121 0.5877 0.052 Uiso 1 1 calc R . . C20 C 0.2764(5) 0.3959(4) 0.4807(3) 0.0434(8) Uani 1 1 d . . . H20A H 0.3188 0.4537 0.4168 0.052 Uiso 1 1 calc 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 Co1 0.0289(2) 0.0223(2) 0.0227(2) -0.00715(14) -0.00150(14) -0.00204(15) O1 0.0338(11) 0.0275(10) 0.0362(11) -0.0146(9) 0.0013(8) 0.0001(8) O2 0.0446(12) 0.0351(12) 0.0380(12) -0.0158(9) -0.0121(10) 0.0087(10) O3 0.0369(11) 0.0249(10) 0.0336(11) -0.0104(8) -0.0018(9) 0.0033(8) O4 0.0546(14) 0.0386(12) 0.0403(12) -0.0208(10) -0.0122(11) 0.0043(10) N1 0.0307(12) 0.0266(12) 0.0307(12) -0.0111(10) 0.0001(9) -0.0045(10) N2 0.0289(12) 0.0234(11) 0.0273(11) -0.0079(9) 0.0011(9) -0.0037(9) O1W 0.0484(13) 0.0294(11) 0.0283(10) -0.0107(8) 0.0051(9) -0.0128(9) C1 0.0299(14) 0.0205(13) 0.0273(14) -0.0046(10) 0.0039(11) -0.0041(11) C2 0.0254(13) 0.0234(13) 0.0281(13) -0.0071(10) 0.0050(10) -0.0061(11) C3 0.0288(14) 0.0239(13) 0.0258(13) -0.0064(10) 0.0010(10) -0.0049(11) C4 0.0311(14) 0.0262(14) 0.0260(13) -0.0059(11) 0.0038(11) -0.0045(11) C5 0.0249(13) 0.0234(13) 0.0283(13) -0.0077(11) 0.0043(10) -0.0061(11) C6 0.0301(14) 0.0211(13) 0.0253(13) -0.0072(10) -0.0014(11) -0.0008(10) C7 0.0315(14) 0.0199(13) 0.0297(14) -0.0089(11) 0.0009(11) -0.0003(11) C8 0.0262(14) 0.0268(14) 0.0410(16) -0.0111(12) -0.0036(12) -0.0011(11) C9 0.0350(15) 0.0267(14) 0.0283(14) -0.0091(11) -0.0036(11) 0.0014(11) C10 0.0320(15) 0.0378(16) 0.0424(17) -0.0192(14) -0.0087(13) -0.0037(12) C11 0.0355(16) 0.0350(16) 0.0402(16) -0.0147(13) -0.0004(13) -0.0090(13) C12 0.0307(15) 0.0271(14) 0.0387(16) -0.0171(12) 0.0012(12) -0.0057(11) C13 0.053(2) 0.0386(18) 0.0264(15) -0.0030(13) 0.0067(13) -0.0073(15) C14 0.0355(16) 0.0344(16) 0.0332(15) -0.0093(12) 0.0003(12) -0.0096(13) C15 0.0385(16) 0.0246(14) 0.0347(15) -0.0068(12) 0.0059(12) -0.0033(12) C16 0.0390(17) 0.0423(17) 0.0332(16) -0.0159(13) -0.0078(13) -0.0022(14) C17 0.0518(19) 0.0371(17) 0.0240(14) -0.0057(12) -0.0040(13) -0.0034(14) C18 0.0323(16) 0.0438(18) 0.0460(18) -0.0167(15) -0.0049(13) -0.0109(13) C19 0.0390(18) 0.0377(17) 0.057(2) -0.0164(15) 0.0096(15) -0.0170(14) C20 0.0476(19) 0.0351(17) 0.0444(18) -0.0076(14) 0.0124(15) -0.0146(15) _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 Co1 O3 2.0300(19) 1_465 ? Co1 N2 2.095(2) . ? Co1 O1W 2.110(2) . ? Co1 N1 2.121(2) . ? Co1 O2 2.192(2) . ? Co1 O1 2.195(2) . ? O1 C4 1.265(3) . ? O2 C4 1.253(4) . ? O3 C1 1.290(3) . ? O3 Co1 2.0300(19) 1_645 ? O4 C1 1.218(4) . ? N1 C11 1.331(4) . ? N1 C7 1.362(4) . ? N2 C14 1.320(4) . ? N2 C6 1.348(3) . ? C1 C5 1.513(4) . ? C2 C12 1.385(4) . ? C2 C3 1.389(4) . ? C2 C4 1.494(4) . ? C3 C5 1.390(4) . ? C5 C8 1.389(4) . ? C6 C9 1.402(4) . ? C6 C7 1.442(4) . ? C7 C15 1.397(4) . ? C8 C10 1.386(4) . ? C9 C16 1.412(5) . ? C9 C17 1.433(4) . ? C10 C12 1.387(4) . ? C11 C19 1.391(5) . ? C13 C17 1.349(5) . ? C13 C15 1.427(5) . ? C14 C18 1.392(4) . ? C15 C20 1.408(5) . ? C16 C18 1.369(5) . ? C19 C20 1.365(5) . ? 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 O3 Co1 N2 112.32(8) 1_465 . ? O3 Co1 O1W 89.91(8) 1_465 . ? N2 Co1 O1W 92.63(9) . . ? O3 Co1 N1 96.55(9) 1_465 . ? N2 Co1 N1 78.93(9) . . ? O1W Co1 N1 170.84(8) . . ? O3 Co1 O2 155.08(8) 1_465 . ? N2 Co1 O2 92.54(8) . . ? O1W Co1 O2 87.11(9) . . ? N1 Co1 O2 89.69(9) . . ? O3 Co1 O1 95.88(8) 1_465 . ? N2 Co1 O1 151.50(8) . . ? O1W Co1 O1 91.41(8) . . ? N1 Co1 O1 94.36(9) . . ? O2 Co1 O1 59.50(8) . . ? C4 O1 Co1 89.98(17) . . ? C4 O2 Co1 90.42(17) . . ? C1 O3 Co1 122.23(18) . 1_645 ? C11 N1 C7 117.9(3) . . ? C11 N1 Co1 129.2(2) . . ? C7 N1 Co1 112.83(19) . . ? C14 N2 C6 118.5(2) . . ? C14 N2 Co1 127.56(19) . . ? C6 N2 Co1 113.84(18) . . ? O4 C1 O3 124.3(3) . . ? O4 C1 C5 120.0(2) . . ? O3 C1 C5 115.7(2) . . ? C12 C2 C3 120.1(2) . . ? C12 C2 C4 120.2(2) . . ? C3 C2 C4 119.6(2) . . ? C2 C3 C5 120.7(3) . . ? O2 C4 O1 119.7(3) . . ? O2 C4 C2 120.0(2) . . ? O1 C4 C2 120.3(2) . . ? C8 C5 C3 118.7(3) . . ? C8 C5 C1 122.0(2) . . ? C3 C5 C1 119.3(2) . . ? N2 C6 C9 123.2(3) . . ? N2 C6 C7 117.5(2) . . ? C9 C6 C7 119.2(3) . . ? N1 C7 C15 123.1(3) . . ? N1 C7 C6 116.8(2) . . ? C15 C7 C6 120.0(3) . . ? C10 C8 C5 120.7(3) . . ? C6 C9 C16 116.8(3) . . ? C6 C9 C17 119.6(3) . . ? C16 C9 C17 123.6(3) . . ? C8 C10 C12 120.3(3) . . ? N1 C11 C19 122.6(3) . . ? C2 C12 C10 119.5(3) . . ? C17 C13 C15 121.7(3) . . ? N2 C14 C18 122.6(3) . . ? C7 C15 C20 117.2(3) . . ? C7 C15 C13 119.0(3) . . ? C20 C15 C13 123.9(3) . . ? C18 C16 C9 119.3(3) . . ? C13 C17 C9 120.5(3) . . ? C16 C18 C14 119.6(3) . . ? C20 C19 C11 119.7(3) . . ? C19 C20 C15 119.5(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.572 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.074 data_10 _database_code_depnum_ccdc_archive 'CCDC 701825' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H30 Co3 N4 O16' _chemical_formula_weight 975.45 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 30.386(5) _cell_length_b 11.0580(19) _cell_length_c 12.034(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.592(3) _cell_angle_gamma 90.00 _cell_volume 3974.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6525 _cell_measurement_theta_min 2.056 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1980 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5706 _exptl_absorpt_correction_T_max 0.9371 _exptl_absorpt_process_details Sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13295 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3415 _reflns_number_gt 3073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+118.0831P] 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 3415 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.2387 _refine_ls_wR_factor_gt 0.2353 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Co1 Co 0.38714(3) 0.59189(9) -0.52844(8) 0.0200(3) Uani 1 1 d . . . Co2 Co 0.5000 0.44756(13) -0.2500 0.0209(4) Uani 1 2 d S . . O1 O 0.46156(18) 0.5728(5) -0.1992(5) 0.0279(12) Uani 1 1 d . . . O2 O 0.39912(18) 0.4749(5) -0.1812(4) 0.0242(12) Uani 1 1 d . . . O3 O 0.38087(19) 0.6488(5) -0.3689(4) 0.0271(12) Uani 1 1 d . . . O4 O 0.3457(2) 0.8244(6) -0.3962(5) 0.0462(18) Uani 1 1 d . . . O5 O 0.43929(19) 0.5185(5) 0.0499(5) 0.0269(12) Uani 1 1 d . . . O6 O 0.4702(2) 0.6764(5) 0.1440(5) 0.0313(13) Uani 1 1 d . . . O1W O 0.3355(2) 0.7215(6) -0.6011(5) 0.0365(14) Uani 1 1 d . . . H1WA H 0.3223 0.7708 -0.5540 0.044 Uiso 1 1 calc R . . H1WB H 0.3268 0.7273 -0.6791 0.044 Uiso 1 1 calc R . . N1 N 0.4341(2) 0.7324(6) -0.5284(6) 0.0270(15) Uani 1 1 d . . . N2 N 0.3356(2) 0.4617(6) -0.5190(6) 0.0292(15) Uani 1 1 d . . . C1 C 0.4059(2) 0.6864(7) -0.1367(6) 0.0218(16) Uani 1 1 d . . . C2 C 0.4174(3) 0.7162(7) -0.0215(7) 0.0243(16) Uani 1 1 d . . . C3 C 0.4030(3) 0.8231(8) 0.0182(7) 0.0324(19) Uani 1 1 d . . . H3A H 0.4109 0.8412 0.0947 0.039 Uiso 1 1 calc R . . C4 C 0.3772(3) 0.9035(8) -0.0521(8) 0.039(2) Uani 1 1 d . . . H4A H 0.3672 0.9746 -0.0238 0.047 Uiso 1 1 calc R . . C5 C 0.3664(3) 0.8767(8) -0.1666(7) 0.035(2) Uani 1 1 d . . . H5A H 0.3491 0.9311 -0.2151 0.042 Uiso 1 1 calc R . . C6 C 0.3806(3) 0.7713(7) -0.2099(7) 0.0263(17) Uani 1 1 d . . . C7 C 0.4225(3) 0.5675(7) -0.1782(6) 0.0235(16) Uani 1 1 d . . . C8 C 0.4439(2) 0.6306(7) 0.0613(6) 0.0237(16) Uani 1 1 d . . . C9 C 0.3677(2) 0.7475(7) -0.3349(7) 0.0266(17) Uani 1 1 d . . . C10 C 0.4341(3) 0.8087(9) -0.6148(8) 0.039(2) Uani 1 1 d . . . H10A H 0.4157 0.7906 -0.6835 0.047 Uiso 1 1 calc R . . C11 C 0.4593(3) 0.9117(8) -0.6084(8) 0.037(2) Uani 1 1 d . . . H11A H 0.4582 0.9608 -0.6717 0.045 Uiso 1 1 calc R . . C12 C 0.4871(3) 0.9431(7) -0.5056(7) 0.0263(17) Uani 1 1 d . . . C13 C 0.4893(3) 0.8612(8) -0.4199(7) 0.0321(19) Uani 1 1 d . . . H13A H 0.5089 0.8744 -0.3520 0.039 Uiso 1 1 calc R . . C14 C 0.4627(3) 0.7584(8) -0.4331(8) 0.0318(19) Uani 1 1 d . . . H14A H 0.4647 0.7051 -0.3725 0.038 Uiso 1 1 calc R . . C15 C 0.3301(3) 0.4173(9) -0.4203(8) 0.041(2) Uani 1 1 d . . . H15A H 0.3490 0.4435 -0.3551 0.049 Uiso 1 1 calc R . . C16 C 0.2975(3) 0.3343(9) -0.4102(8) 0.043(2) Uani 1 1 d . . . H16A H 0.2954 0.3039 -0.3392 0.052 Uiso 1 1 calc R . . C17 C 0.2677(3) 0.2953(8) -0.5040(7) 0.034(2) Uani 1 1 d . . . C18 C 0.2746(3) 0.3384(10) -0.6066(8) 0.044(2) Uani 1 1 d . . . H18A H 0.2564 0.3128 -0.6732 0.052 Uiso 1 1 calc R . . C19 C 0.3088(3) 0.4201(9) -0.6104(8) 0.038(2) Uani 1 1 d . . . H19A H 0.3132 0.4473 -0.6807 0.046 Uiso 1 1 calc R . . O2W O 0.2555(5) 0.836(2) -0.390(2) 0.224(11) Uani 1 1 d . . . H2WA H 0.2592 0.8109 -0.3225 0.269 Uiso 1 1 d R . . H2WB H 0.2348 0.8866 -0.4143 0.269 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 Co1 0.0184(5) 0.0179(6) 0.0239(6) -0.0002(4) 0.0041(4) -0.0031(4) Co2 0.0183(7) 0.0185(8) 0.0265(8) 0.000 0.0053(6) 0.000 O1 0.017(3) 0.032(3) 0.037(3) -0.004(2) 0.009(2) -0.001(2) O2 0.027(3) 0.024(3) 0.024(3) -0.001(2) 0.010(2) -0.002(2) O3 0.034(3) 0.023(3) 0.024(3) 0.000(2) 0.006(2) 0.003(2) O4 0.056(4) 0.043(4) 0.035(4) 0.002(3) -0.005(3) 0.026(3) O5 0.024(3) 0.022(3) 0.031(3) 0.000(2) -0.002(2) 0.001(2) O6 0.034(3) 0.030(3) 0.026(3) 0.002(2) -0.005(2) -0.003(2) O1W 0.039(4) 0.036(3) 0.034(3) 0.002(3) 0.006(3) 0.008(3) N1 0.023(3) 0.017(3) 0.041(4) 0.000(3) 0.006(3) -0.003(3) N2 0.024(4) 0.029(4) 0.034(4) -0.003(3) 0.005(3) -0.007(3) C1 0.014(3) 0.024(4) 0.027(4) 0.000(3) 0.004(3) -0.004(3) C2 0.028(4) 0.019(4) 0.025(4) 0.000(3) 0.002(3) 0.002(3) C3 0.039(5) 0.031(5) 0.026(4) -0.004(3) 0.004(4) 0.004(4) C4 0.047(6) 0.022(4) 0.045(5) -0.006(4) 0.002(4) 0.015(4) C5 0.047(5) 0.023(4) 0.034(5) 0.005(4) 0.003(4) 0.014(4) C6 0.026(4) 0.021(4) 0.032(4) 0.000(3) 0.007(3) 0.003(3) C7 0.030(4) 0.022(4) 0.017(4) 0.000(3) 0.000(3) 0.004(3) C8 0.019(4) 0.028(4) 0.024(4) 0.000(3) 0.004(3) 0.006(3) C9 0.016(4) 0.030(4) 0.033(4) 0.002(3) 0.002(3) 0.000(3) C10 0.049(6) 0.038(5) 0.029(5) -0.001(4) 0.002(4) -0.017(4) C11 0.054(6) 0.024(5) 0.032(5) 0.007(3) 0.000(4) -0.016(4) C12 0.024(4) 0.016(4) 0.038(5) 0.001(3) 0.006(3) 0.000(3) C13 0.032(4) 0.028(4) 0.034(5) 0.004(4) 0.000(4) -0.010(4) C14 0.030(4) 0.022(4) 0.042(5) 0.011(4) 0.003(4) -0.003(3) C15 0.040(5) 0.053(6) 0.030(5) -0.006(4) 0.005(4) -0.027(5) C16 0.044(5) 0.049(6) 0.036(5) 0.002(4) 0.006(4) -0.026(5) C17 0.032(4) 0.035(5) 0.036(5) -0.003(4) 0.012(4) -0.015(4) C18 0.039(5) 0.057(6) 0.034(5) 0.000(4) 0.002(4) -0.023(5) C19 0.031(5) 0.048(6) 0.036(5) 0.004(4) 0.006(4) -0.017(4) O2W 0.053(8) 0.35(3) 0.27(2) -0.01(2) 0.016(11) 0.037(14) _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 Co1 O3 2.063(5) . ? Co1 O2 2.075(5) 6_565 ? Co1 O5 2.084(6) 6_565 ? Co1 N1 2.110(6) . ? Co1 N2 2.146(7) . ? Co1 O1W 2.185(6) . ? Co2 O6 1.975(6) 5_665 ? Co2 O6 1.975(6) 6_565 ? Co2 O1 1.979(6) 2_654 ? Co2 O1 1.979(6) . ? O1 C7 1.259(10) . ? O2 C7 1.243(10) . ? O2 Co1 2.075(5) 6_566 ? O3 C9 1.256(10) . ? O4 C9 1.239(10) . ? O5 C8 1.252(10) . ? O5 Co1 2.084(6) 6_566 ? O6 C8 1.264(10) . ? O6 Co2 1.975(6) 5_665 ? O1W H1WA 0.9300 . ? O1W H1WB 0.9300 . ? N1 C14 1.337(11) . ? N1 C10 1.339(11) . ? N2 C15 1.324(12) . ? N2 C19 1.325(11) . ? C1 C2 1.404(11) . ? C1 C6 1.414(11) . ? C1 C7 1.526(11) . ? C2 C3 1.377(11) . ? C2 C8 1.497(11) . ? C3 C4 1.369(12) . ? C3 H3A 0.9300 . ? C4 C5 1.388(13) . ? C4 H4A 0.9300 . ? C5 C6 1.378(12) . ? C5 H5A 0.9300 . ? C6 C9 1.506(12) . ? C10 C11 1.368(12) . ? C10 H10A 0.9300 . ? C11 C12 1.407(12) . ? C11 H11A 0.9300 . ? C12 C13 1.365(12) . ? C12 C12 1.475(15) 5_674 ? C13 C14 1.388(12) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.372(13) . ? C15 H15A 0.9300 . ? C16 C17 1.380(13) . ? C16 H16A 0.9300 . ? C17 C18 1.376(13) . ? C17 C17 1.485(16) 7_554 ? C18 C19 1.383(13) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8501 . ? 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 O3 Co1 O2 174.2(2) . 6_565 ? O3 Co1 O5 87.1(2) . 6_565 ? O2 Co1 O5 87.1(2) 6_565 6_565 ? O3 Co1 N1 87.3(3) . . ? O2 Co1 N1 91.9(2) 6_565 . ? O5 Co1 N1 88.5(2) 6_565 . ? O3 Co1 N2 87.8(2) . . ? O2 Co1 N2 93.3(2) 6_565 . ? O5 Co1 N2 94.9(2) 6_565 . ? N1 Co1 N2 174.0(3) . . ? O3 Co1 O1W 89.4(2) . . ? O2 Co1 O1W 96.2(2) 6_565 . ? O5 Co1 O1W 174.7(2) 6_565 . ? N1 Co1 O1W 87.3(3) . . ? N2 Co1 O1W 89.1(3) . . ? O6 Co2 O6 92.1(3) 5_665 6_565 ? O6 Co2 O1 117.3(2) 5_665 2_654 ? O6 Co2 O1 120.9(2) 6_565 2_654 ? O6 Co2 O1 120.9(2) 5_665 . ? O6 Co2 O1 117.3(2) 6_565 . ? O1 Co2 O1 91.2(3) 2_654 . ? C7 O1 Co2 131.4(5) . . ? C7 O2 Co1 117.4(5) . 6_566 ? C9 O3 Co1 131.1(5) . . ? C8 O5 Co1 133.6(5) . 6_566 ? C8 O6 Co2 112.3(5) . 5_665 ? Co1 O1W H1WA 120.0 . . ? Co1 O1W H1WB 120.0 . . ? H1WA O1W H1WB 120.0 . . ? C14 N1 C10 116.0(7) . . ? C14 N1 Co1 119.4(5) . . ? C10 N1 Co1 124.1(6) . . ? C15 N2 C19 117.2(7) . . ? C15 N2 Co1 120.7(6) . . ? C19 N2 Co1 122.1(6) . . ? C2 C1 C6 117.9(7) . . ? C2 C1 C7 119.2(7) . . ? C6 C1 C7 122.9(7) . . ? C3 C2 C1 120.4(7) . . ? C3 C2 C8 118.6(7) . . ? C1 C2 C8 120.9(7) . . ? C4 C3 C2 121.7(8) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 118.6(8) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 121.5(8) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C1 119.9(7) . . ? C5 C6 C9 118.9(7) . . ? C1 C6 C9 121.2(7) . . ? O2 C7 O1 126.0(7) . . ? O2 C7 C1 119.8(7) . . ? O1 C7 C1 114.1(7) . . ? O5 C8 O6 121.6(7) . . ? O5 C8 C2 121.2(7) . . ? O6 C8 C2 117.2(7) . . ? O4 C9 O3 124.9(8) . . ? O4 C9 C6 119.2(7) . . ? O3 C9 C6 115.9(7) . . ? N1 C10 C11 124.1(8) . . ? N1 C10 H10A 117.9 . . ? C11 C10 H10A 117.9 . . ? C10 C11 C12 119.7(8) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C13 C12 C11 116.0(7) . . ? C13 C12 C12 123.1(10) . 5_674 ? C11 C12 C12 120.9(9) . 5_674 ? C12 C13 C14 120.7(8) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? N1 C14 C13 123.2(8) . . ? N1 C14 H14A 118.4 . . ? C13 C14 H14A 118.4 . . ? N2 C15 C16 122.7(8) . . ? N2 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C15 C16 C17 120.8(9) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C18 C17 C16 116.1(8) . . ? C18 C17 C17 121.6(10) . 7_554 ? C16 C17 C17 122.1(10) . 7_554 ? C17 C18 C19 119.7(9) . . ? C17 C18 H18A 120.2 . . ? C19 C18 H18A 120.2 . . ? N2 C19 C18 123.4(9) . . ? N2 C19 H19A 118.3 . . ? C18 C19 H19A 118.3 . . ? H2WA O2W H2WB 120.0 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 2.957 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.186 data_11 _database_code_depnum_ccdc_archive 'CCDC 701826' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2 Ni O8' _chemical_formula_weight 459.05 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.2803(10) _cell_length_b 8.4929(7) _cell_length_c 19.9649(17) _cell_angle_alpha 90.00 _cell_angle_beta 102.315(2) _cell_angle_gamma 90.00 _cell_volume 1868.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5141 _cell_measurement_theta_min 2.615 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6512 _exptl_absorpt_correction_T_max 0.8802 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9958 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4051 _reflns_number_gt 3565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4051 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _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 Ni1 Ni 1.19792(2) 0.85119(3) 1.176162(12) 0.01868(12) Uani 1 1 d . . . O1 O 1.20333(12) 0.61223(17) 1.19659(8) 0.0237(3) Uani 1 1 d . . . O2 O 1.27417(13) 0.36995(15) 1.21970(7) 0.0234(3) Uani 1 1 d . . . O3 O 1.15460(13) 0.81246(16) 1.06955(7) 0.0256(3) Uani 1 1 d . . . O4 O 1.01296(14) 0.62641(17) 1.05131(8) 0.0315(4) Uani 1 1 d . . . O5 O 1.07906(17) 0.6312(2) 0.90941(9) 0.0417(4) Uani 1 1 d . . . O6 O 1.26232(18) 0.6864(2) 0.89396(10) 0.0523(5) Uani 1 1 d . . . N1 N 1.38300(16) 0.84664(19) 1.17584(9) 0.0247(4) Uani 1 1 d . . . N2 N 2.01107(16) 0.84659(18) 1.17675(9) 0.0228(4) Uani 1 1 d . . . O1W O 1.19029(15) 1.08641(19) 1.15563(10) 0.0292(3) Uani 1 1 d . . . H1WA H 1.221(3) 1.152(4) 1.1805(18) 0.061(12) Uiso 1 1 d . . . H1WB H 1.181(3) 1.117(4) 1.117(2) 0.070(11) Uiso 1 1 d . . . O2W O 1.1419(3) 1.1305(3) 1.02070(12) 0.0617(7) Uani 1 1 d . . . H2WA H 1.091(4) 1.199(5) 0.995(2) 0.119(16) Uiso 1 1 d . . . H2WB H 1.117(3) 1.043(4) 1.0119(17) 0.077(13) Uiso 1 1 d . . . C1 C 1.21835(18) 0.5528(2) 1.05355(10) 0.0227(4) Uani 1 1 d . . . C2 C 1.2545(2) 0.5316(2) 0.99110(10) 0.0267(4) Uani 1 1 d . . . C3 C 1.3504(2) 0.4326(3) 0.98706(11) 0.0339(5) Uani 1 1 d . . . H3 H 1.3744 0.4211 0.9456 0.041 Uiso 1 1 calc R . . C4 C 1.4107(2) 0.3509(3) 1.04394(13) 0.0360(6) Uani 1 1 d . . . H4 H 1.4744 0.2838 1.0408 0.043 Uiso 1 1 calc R . . C5 C 1.3756(2) 0.3696(2) 1.10551(12) 0.0297(5) Uani 1 1 d . . . H5 H 1.4158 0.3142 1.1438 0.036 Uiso 1 1 calc R . . C6 C 1.28037(17) 0.4707(2) 1.11106(10) 0.0221(4) Uani 1 1 d . . . C7 C 1.1991(2) 0.6216(3) 0.92753(12) 0.0334(5) Uani 1 1 d . . . C8 C 1.11971(19) 0.6708(2) 1.05885(10) 0.0230(4) Uani 1 1 d . . . C9 C 1.24940(17) 0.4875(2) 1.18044(9) 0.0188(4) Uani 1 1 d . . . C10 C 1.4240(2) 0.8960(3) 1.12099(12) 0.0355(5) Uani 1 1 d . . . H10 H 1.3683 0.9330 1.0830 0.043 Uiso 1 1 calc R . . C11 C 1.5455(2) 0.8939(3) 1.11881(12) 0.0375(5) Uani 1 1 d . . . H11 H 1.5701 0.9285 1.0797 0.045 Uiso 1 1 calc R . . C12 C 1.6311(2) 0.8403(2) 1.17484(12) 0.0270(5) Uani 1 1 d . . . C13 C 1.5873(2) 0.7897(3) 1.23143(12) 0.0345(5) Uani 1 1 d . . . H13 H 1.6407 0.7522 1.2702 0.041 Uiso 1 1 calc R . . C14 C 1.4652(2) 0.7954(3) 1.22972(11) 0.0330(5) Uani 1 1 d . . . H14 H 1.4382 0.7618 1.2682 0.040 Uiso 1 1 calc R . . C15 C 1.7619(2) 0.8398(2) 1.17533(12) 0.0269(5) Uani 1 1 d . . . C16 C 1.8401(2) 0.7242(3) 1.20815(13) 0.0395(6) Uani 1 1 d . . . H16 H 1.8103 0.6421 1.2306 0.047 Uiso 1 1 calc R . . C17 C 1.9613(2) 0.7309(3) 1.20742(13) 0.0352(5) Uani 1 1 d . . . H17 H 2.0116 0.6512 1.2293 0.042 Uiso 1 1 calc R . . C18 C 1.81325(19) 0.9581(3) 1.14295(12) 0.0322(5) Uani 1 1 d . . . H18 H 1.7648 1.0376 1.1195 0.039 Uiso 1 1 calc R . . C19 C 1.93589(19) 0.9576(3) 1.14564(11) 0.0305(5) Uani 1 1 d . . . H19 H 1.9683 1.0397 1.1245 0.037 Uiso 1 1 calc R . . H5A H 1.048(3) 0.541(4) 0.9291(18) 0.092(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01462(17) 0.02082(18) 0.02022(17) -0.00061(9) 0.00286(11) -0.00040(8) O1 0.0237(8) 0.0215(7) 0.0258(7) -0.0007(6) 0.0049(6) 0.0024(6) O2 0.0286(8) 0.0205(7) 0.0208(7) 0.0022(5) 0.0049(6) 0.0023(5) O3 0.0294(8) 0.0209(7) 0.0245(7) -0.0002(6) 0.0012(6) 0.0000(6) O4 0.0202(8) 0.0340(8) 0.0375(9) -0.0063(7) 0.0000(7) -0.0022(6) O5 0.0383(11) 0.0473(11) 0.0353(10) 0.0118(8) -0.0013(8) -0.0006(8) O6 0.0558(13) 0.0596(11) 0.0447(11) 0.0239(9) 0.0176(9) -0.0012(10) N1 0.0164(9) 0.0328(10) 0.0249(9) 0.0006(7) 0.0043(7) -0.0007(7) N2 0.0153(9) 0.0273(9) 0.0261(9) -0.0001(7) 0.0049(7) 0.0002(6) O1W 0.0349(9) 0.0228(8) 0.0276(8) -0.0016(7) 0.0015(7) -0.0044(6) O2W 0.0911(19) 0.0417(12) 0.0410(12) 0.0065(10) -0.0112(11) -0.0013(12) C1 0.0229(10) 0.0219(9) 0.0228(9) -0.0012(8) 0.0039(8) -0.0016(8) C2 0.0301(11) 0.0257(10) 0.0245(10) 0.0015(8) 0.0059(8) -0.0019(8) C3 0.0399(13) 0.0368(12) 0.0290(11) 0.0004(10) 0.0163(10) 0.0015(10) C4 0.0343(13) 0.0399(13) 0.0377(13) 0.0042(10) 0.0161(11) 0.0114(10) C5 0.0262(12) 0.0321(12) 0.0316(12) 0.0075(9) 0.0077(9) 0.0083(9) C6 0.0216(10) 0.0220(10) 0.0231(9) 0.0010(8) 0.0054(8) 0.0001(8) C7 0.0444(15) 0.0299(11) 0.0254(11) 0.0001(9) 0.0065(10) -0.0013(10) C8 0.0262(11) 0.0242(10) 0.0163(9) 0.0016(8) -0.0003(8) 0.0023(8) C9 0.0144(9) 0.0206(9) 0.0204(9) 0.0004(8) 0.0013(7) -0.0028(7) C10 0.0202(11) 0.0569(14) 0.0285(11) 0.0087(11) 0.0035(9) 0.0024(10) C11 0.0219(12) 0.0600(15) 0.0321(12) 0.0137(11) 0.0091(9) 0.0031(11) C12 0.0181(11) 0.0319(12) 0.0314(12) -0.0002(9) 0.0060(9) -0.0012(8) C13 0.0205(11) 0.0510(14) 0.0313(12) 0.0119(11) 0.0037(9) 0.0042(10) C14 0.0231(11) 0.0486(13) 0.0282(11) 0.0102(10) 0.0072(9) 0.0010(10) C15 0.0187(11) 0.0335(12) 0.0287(11) 0.0006(9) 0.0054(8) 0.0021(8) C16 0.0241(12) 0.0405(13) 0.0558(15) 0.0196(12) 0.0127(11) 0.0006(10) C17 0.0210(11) 0.0349(12) 0.0503(14) 0.0145(11) 0.0092(10) 0.0061(9) C18 0.0201(11) 0.0347(12) 0.0415(13) 0.0100(10) 0.0058(9) 0.0049(9) C19 0.0207(11) 0.0327(12) 0.0380(12) 0.0074(10) 0.0060(9) 0.0009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O1W 2.0375(16) . ? Ni1 O2 2.0416(14) 2_757 ? Ni1 O1 2.0683(15) . ? Ni1 N1 2.0895(19) . ? Ni1 O3 2.1058(14) . ? Ni1 N2 2.1105(18) 1_455 ? O1 C9 1.252(2) . ? O2 C9 1.263(2) . ? O2 Ni1 2.0416(14) 2_747 ? O3 C8 1.270(2) . ? O4 C8 1.240(3) . ? O5 C7 1.327(3) . ? O5 H5A 0.96(4) . ? O6 C7 1.210(3) . ? N1 C14 1.334(3) . ? N1 C10 1.343(3) . ? N2 C19 1.330(3) . ? N2 C17 1.342(3) . ? N2 Ni1 2.1105(17) 1_655 ? O1W H1WA 0.78(4) . ? O1W H1WB 0.81(4) . ? O2W H2WA 0.89(5) . ? O2W H2WB 0.80(4) . ? C1 C6 1.397(3) . ? C1 C2 1.403(3) . ? C1 C8 1.518(3) . ? C2 C3 1.386(3) . ? C2 C7 1.499(3) . ? C3 C4 1.380(3) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.398(3) . ? C5 H5 0.9300 . ? C6 C9 1.506(2) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 H11 0.9300 . ? C12 C13 1.394(3) . ? C12 C15 1.473(3) . ? C13 C14 1.371(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C18 1.386(3) . ? C15 C16 1.388(3) . ? C16 C17 1.372(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.373(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1W Ni1 O2 96.84(6) . 2_757 ? O1W Ni1 O1 179.28(6) . . ? O2 Ni1 O1 83.34(5) 2_757 . ? O1W Ni1 N1 90.97(7) . . ? O2 Ni1 N1 93.86(7) 2_757 . ? O1 Ni1 N1 89.71(6) . . ? O1W Ni1 O3 87.65(7) . . ? O2 Ni1 O3 173.60(5) 2_757 . ? O1 Ni1 O3 92.11(6) . . ? N1 Ni1 O3 90.61(6) . . ? O1W Ni1 N2 91.14(6) . 1_455 ? O2 Ni1 N2 86.16(6) 2_757 1_455 ? O1 Ni1 N2 88.18(6) . 1_455 ? N1 Ni1 N2 177.88(6) . 1_455 ? O3 Ni1 N2 89.20(6) . 1_455 ? C9 O1 Ni1 140.87(13) . . ? C9 O2 Ni1 131.24(12) . 2_747 ? C8 O3 Ni1 108.35(12) . . ? C7 O5 H5A 106(2) . . ? C14 N1 C10 117.27(19) . . ? C14 N1 Ni1 121.76(14) . . ? C10 N1 Ni1 120.97(15) . . ? C19 N2 C17 116.40(18) . . ? C19 N2 Ni1 121.49(13) . 1_655 ? C17 N2 Ni1 122.10(14) . 1_655 ? Ni1 O1W H1WA 126(2) . . ? Ni1 O1W H1WB 120(2) . . ? H1WA O1W H1WB 109(3) . . ? H2WA O2W H2WB 109(4) . . ? C6 C1 C2 118.47(18) . . ? C6 C1 C8 121.21(17) . . ? C2 C1 C8 120.19(18) . . ? C3 C2 C1 120.52(19) . . ? C3 C2 C7 116.70(19) . . ? C1 C2 C7 122.63(19) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 120.00(18) . . ? C1 C6 C9 122.35(17) . . ? C5 C6 C9 117.66(18) . . ? O6 C7 O5 120.6(2) . . ? O6 C7 C2 120.8(2) . . ? O5 C7 C2 118.6(2) . . ? O4 C8 O3 124.51(19) . . ? O4 C8 C1 119.89(18) . . ? O3 C8 C1 115.58(18) . . ? O1 C9 O2 123.92(18) . . ? O1 C9 C6 120.50(17) . . ? O2 C9 C6 115.58(16) . . ? N1 C10 C11 122.6(2) . . ? N1 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 116.6(2) . . ? C11 C12 C15 122.0(2) . . ? C13 C12 C15 121.4(2) . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N1 C14 C13 123.6(2) . . ? N1 C14 H14 118.2 . . ? C13 C14 H14 118.2 . . ? C18 C15 C16 116.5(2) . . ? C18 C15 C12 120.81(19) . . ? C16 C15 C12 122.67(19) . . ? C17 C16 C15 120.0(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? N2 C17 C16 123.4(2) . . ? N2 C17 H17 118.3 . . ? C16 C17 H17 118.3 . . ? C19 C18 C15 119.8(2) . . ? C19 C18 H18 120.1 . . ? C15 C18 H18 120.1 . . ? N2 C19 C18 123.9(2) . . ? N2 C19 H19 118.1 . . ? C18 C19 H19 118.1 . . ? 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 O1W H1WA O2 0.78(4) 2.05(3) 2.795(2) 161(3) 1_565 O1W H1WA O1 0.78(4) 2.44(3) 2.947(2) 124(3) 2_757 O1W H1WB O2W 0.81(4) 1.88(4) 2.659(3) 163(3) . O2W H2WA O4 0.89(5) 2.00(5) 2.883(3) 172(4) 3_777 O2W H2WB O3 0.80(4) 2.26(4) 2.865(3) 132(3) . O5 H5A O4 0.96(4) 1.67(4) 2.613(2) 170(3) 3_767 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.887 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.086 data_12 _database_code_depnum_ccdc_archive 'CCDC 701827' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H42 Cd5 N6 O26' _chemical_formula_weight 1897.06 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.769(2) _cell_length_b 12.832(3) _cell_length_c 13.313(3) _cell_angle_alpha 115.80(3) _cell_angle_beta 100.81(3) _cell_angle_gamma 90.37(3) _cell_volume 1618.8(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 25 _exptl_crystal_description BLOCK _exptl_crystal_colour LIGHT-YELLOW _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4822 _exptl_absorpt_correction_T_max 0.5863 _exptl_absorpt_process_details SEMI-EMPIRICAL _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 'SIEMENS R3' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% none _diffrn_reflns_number 6376 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6363 _reflns_number_gt 5012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SIEMENS XSCANS' _computing_cell_refinement 'SIEMENS XSCANS' _computing_data_reduction 'SIEMENS SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.1095P)^2^+2.0497P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6363 _refine_ls_number_parameters 474 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cd1 Cd 0.34358(5) 0.13306(4) -1.01560(4) 0.02565(16) Uani 1 1 d . . . Cd2 Cd 0.51470(4) 0.43280(4) -0.81033(4) 0.02602(16) Uani 1 1 d . . . Cd3 Cd 0.0000 0.5000 -1.0000 0.0310(2) Uani 1 2 d S . . O1 O 0.5604(5) 0.1155(4) -0.9748(4) 0.0327(11) Uani 1 1 d . . . O2 O 0.7088(5) -0.0006(4) -1.0408(5) 0.0379(12) Uani 1 1 d . . . O3 O 0.4300(5) 0.2995(4) -1.0233(4) 0.0296(11) Uani 1 1 d . . . O4 O 0.6360(5) 0.3606(4) -0.9520(4) 0.0345(11) Uani 1 1 d . . . O5 O 0.5604(6) 0.4285(4) -1.1410(4) 0.0412(13) Uani 1 1 d . . . O6 O 0.4543(6) 0.3465(5) -1.3175(5) 0.0518(16) Uani 1 1 d . . . O7 O 0.1712(5) 0.2396(5) -1.0169(5) 0.0417(13) Uani 1 1 d . . . O8 O 0.0265(5) 0.3559(5) -0.9392(5) 0.0405(13) Uani 1 1 d . . . O9 O 0.4018(5) 0.2669(4) -0.8224(4) 0.0355(12) Uani 1 1 d . . . O10 O 0.3388(5) 0.4324(5) -0.7126(5) 0.0443(14) Uani 1 1 d . . . O11 O 0.4110(6) 0.2942(6) -0.5783(5) 0.0501(15) Uani 1 1 d . . . O12 O 0.2763(6) 0.2344(5) -0.4985(5) 0.0495(15) Uani 1 1 d . . . H12A H 0.3308 0.2687 -0.4400 0.074 Uiso 1 1 calc R . . O1W O 0.2009(6) 0.4641(6) -1.0423(6) 0.0465(15) Uani 1 1 d . . . H1WA H 0.273(11) 0.532(10) -1.022(9) 0.08(4) Uiso 1 1 d . . . H1WB H 0.229(8) 0.408(7) -1.045(7) 0.04(3) Uiso 1 1 d . . . N1 N 0.3040(6) 0.0211(5) -1.2151(5) 0.0336(14) Uani 1 1 d . . . N2 N 0.0831(6) -0.3577(6) -1.8104(5) 0.0400(16) Uani 1 1 d . . . N3 N 0.7009(6) 0.4370(6) -0.6941(5) 0.0374(15) Uani 1 1 d . . . C1 C 0.6156(7) 0.0996(6) -1.1457(6) 0.0290(15) Uani 1 1 d . . . C2 C 0.6329(9) 0.0130(7) -1.2511(7) 0.044(2) Uani 1 1 d . . . H2 H 0.6616 -0.0567 -1.2555 0.053 Uiso 1 1 calc R . . C3 C 0.6080(10) 0.0303(7) -1.3487(7) 0.053(2) Uani 1 1 d . . . H3 H 0.6194 -0.0280 -1.4178 0.063 Uiso 1 1 calc R . . C4 C 0.5658(8) 0.1351(7) -1.3434(7) 0.0416(19) Uani 1 1 d . . . H4 H 0.5467 0.1459 -1.4091 0.050 Uiso 1 1 calc R . . C5 C 0.5525(7) 0.2230(6) -1.2390(6) 0.0285(15) Uani 1 1 d . . . C6 C 0.5733(6) 0.2060(5) -1.1410(6) 0.0256(14) Uani 1 1 d . . . C7 C 0.6308(6) 0.0709(6) -1.0452(6) 0.0278(14) Uani 1 1 d . . . C8 C 0.5456(6) 0.2968(6) -1.0300(6) 0.0253(14) Uani 1 1 d . . . C9 C 0.5179(7) 0.3399(6) -1.2317(6) 0.0313(15) Uani 1 1 d . . . C10 C 0.1021(6) 0.2306(6) -0.8598(6) 0.0315(15) Uani 1 1 d . . . C11 C 0.2058(6) 0.2578(6) -0.7666(5) 0.0245(13) Uani 1 1 d . . . C12 C 0.1954(7) 0.2224(7) -0.6826(6) 0.0330(16) Uani 1 1 d . . . C13 C 0.0866(9) 0.1539(9) -0.6938(8) 0.052(2) Uani 1 1 d . . . H13 H 0.0801 0.1310 -0.6375 0.062 Uiso 1 1 calc R . . C14 C -0.0122(10) 0.1203(10) -0.7904(8) 0.059(3) Uani 1 1 d . . . H14 H -0.0819 0.0710 -0.8002 0.071 Uiso 1 1 calc R . . C15 C -0.0066(8) 0.1602(8) -0.8716(8) 0.049(2) Uani 1 1 d . . . H15 H -0.0743 0.1406 -0.9335 0.059 Uiso 1 1 calc R . . C16 C 0.0999(7) 0.2788(6) -0.9448(6) 0.0313(15) Uani 1 1 d . . . C17 C 0.3254(6) 0.3257(6) -0.7645(6) 0.0284(15) Uani 1 1 d . . . C18 C 0.3058(8) 0.2546(6) -0.5815(6) 0.0333(16) Uani 1 1 d . . . C19 C 0.3227(9) -0.0927(7) -1.2608(7) 0.0425(19) Uani 1 1 d . . . H19 H 0.3616 -0.1234 -1.2126 0.051 Uiso 1 1 calc R . . C20 C 0.2859(9) -0.1663(7) -1.3775(7) 0.046(2) Uani 1 1 d . . . H20 H 0.3028 -0.2438 -1.4055 0.055 Uiso 1 1 calc R . . C21 C 0.2246(7) -0.1248(7) -1.4516(6) 0.0358(17) Uani 1 1 d . . . C22 C 0.2102(8) -0.0056(7) -1.4046(7) 0.0426(19) Uani 1 1 d . . . H22 H 0.1728 0.0271 -1.4515 0.051 Uiso 1 1 calc R . . C23 C 0.2515(8) 0.0632(7) -1.2888(6) 0.0397(18) Uani 1 1 d . . . H23 H 0.2428 0.1425 -1.2601 0.048 Uiso 1 1 calc R . . C24 C 0.1759(7) -0.2048(7) -1.5769(6) 0.0367(17) Uani 1 1 d . . . C25 C 0.2255(7) -0.3111(6) -1.6285(6) 0.0326(16) Uani 1 1 d . . . H25 H 0.2898 -0.3334 -1.5868 0.039 Uiso 1 1 calc R . . C26 C 0.1762(7) -0.3839(6) -1.7448(6) 0.0353(17) Uani 1 1 d . . . H26 H 0.2100 -0.4545 -1.7784 0.042 Uiso 1 1 calc R . . C27 C 0.0820(9) -0.1771(8) -1.6471(7) 0.052(2) Uani 1 1 d . . . H27 H 0.0485 -0.1059 -1.6173 0.062 Uiso 1 1 calc R . . C28 C 0.0389(10) -0.2548(8) -1.7605(7) 0.058(3) Uani 1 1 d . . . H28 H -0.0245 -0.2341 -1.8044 0.070 Uiso 1 1 calc R . . C29 C 0.8109(9) 0.4249(11) -0.7295(8) 0.070(3) Uani 1 1 d . . . H29 H 0.8081 0.3974 -0.8072 0.084 Uiso 1 1 calc R . . C30 C 0.9283(9) 0.4513(12) -0.6560(8) 0.080(4) Uani 1 1 d . . . H30 H 1.0019 0.4450 -0.6844 0.096 Uiso 1 1 calc R . . C31 C 0.9372(7) 0.4869(7) -0.5412(6) 0.0357(17) Uani 1 1 d . . . C32 C 0.8219(7) 0.4928(6) -0.5048(6) 0.0334(16) Uani 1 1 d . . . H32 H 0.8220 0.5129 -0.4287 0.040 Uiso 1 1 calc R . . C33 C 0.7086(7) 0.4687(6) -0.5829(6) 0.0318(15) Uani 1 1 d . . . H33 H 0.6334 0.4748 -0.5568 0.038 Uiso 1 1 calc 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 Cd1 0.0265(3) 0.0240(3) 0.0216(3) 0.0064(2) 0.00356(19) 0.00025(19) Cd2 0.0235(3) 0.0254(3) 0.0245(3) 0.0090(2) 0.00001(19) -0.00064(19) Cd3 0.0320(4) 0.0305(4) 0.0210(4) 0.0052(3) -0.0003(3) 0.0029(3) O1 0.032(3) 0.035(3) 0.036(3) 0.019(2) 0.007(2) 0.007(2) O2 0.032(3) 0.036(3) 0.053(3) 0.027(3) 0.008(2) 0.008(2) O3 0.031(3) 0.025(2) 0.033(3) 0.011(2) 0.013(2) 0.001(2) O4 0.037(3) 0.033(3) 0.023(2) 0.007(2) -0.002(2) -0.007(2) O5 0.061(4) 0.026(3) 0.032(3) 0.012(2) 0.003(3) 0.007(2) O6 0.071(4) 0.042(3) 0.035(3) 0.018(3) -0.012(3) 0.004(3) O7 0.035(3) 0.063(4) 0.037(3) 0.030(3) 0.013(2) 0.016(3) O8 0.035(3) 0.046(3) 0.044(3) 0.021(3) 0.014(2) 0.014(2) O9 0.030(3) 0.038(3) 0.027(3) 0.004(2) 0.008(2) -0.010(2) O10 0.037(3) 0.031(3) 0.059(4) 0.014(3) 0.011(3) -0.001(2) O11 0.040(3) 0.065(4) 0.041(3) 0.024(3) -0.001(3) -0.005(3) O12 0.063(4) 0.054(4) 0.028(3) 0.018(3) 0.004(3) -0.006(3) O1W 0.035(3) 0.041(3) 0.060(4) 0.019(3) 0.010(3) 0.001(3) N1 0.033(3) 0.029(3) 0.028(3) 0.003(3) 0.007(3) -0.002(3) N2 0.037(4) 0.035(3) 0.035(4) 0.008(3) -0.005(3) 0.006(3) N3 0.029(3) 0.055(4) 0.024(3) 0.017(3) 0.000(3) 0.008(3) C1 0.028(3) 0.027(3) 0.032(4) 0.013(3) 0.007(3) -0.001(3) C2 0.059(5) 0.033(4) 0.040(5) 0.014(4) 0.016(4) 0.017(4) C3 0.078(7) 0.035(4) 0.036(5) 0.004(4) 0.024(5) 0.016(4) C4 0.048(5) 0.042(4) 0.031(4) 0.011(4) 0.011(4) 0.002(4) C5 0.030(4) 0.023(3) 0.026(3) 0.004(3) 0.007(3) -0.004(3) C6 0.027(3) 0.018(3) 0.024(3) 0.004(3) 0.003(3) -0.002(3) C7 0.022(3) 0.025(3) 0.033(4) 0.011(3) 0.004(3) -0.002(3) C8 0.028(3) 0.020(3) 0.027(3) 0.011(3) 0.005(3) -0.002(3) C9 0.036(4) 0.028(4) 0.031(4) 0.014(3) 0.008(3) 0.002(3) C10 0.024(3) 0.035(4) 0.029(4) 0.009(3) 0.003(3) -0.004(3) C11 0.019(3) 0.023(3) 0.024(3) 0.004(3) 0.003(3) -0.002(2) C12 0.032(4) 0.040(4) 0.028(4) 0.016(3) 0.009(3) 0.006(3) C13 0.047(5) 0.072(6) 0.052(5) 0.040(5) 0.018(4) -0.001(4) C14 0.051(5) 0.083(7) 0.059(6) 0.046(6) 0.012(5) -0.004(5) C15 0.030(4) 0.060(5) 0.055(5) 0.029(5) -0.005(4) -0.018(4) C16 0.027(4) 0.035(4) 0.024(3) 0.009(3) -0.001(3) -0.001(3) C17 0.025(3) 0.032(4) 0.023(3) 0.010(3) -0.003(3) -0.005(3) C18 0.042(4) 0.029(4) 0.027(4) 0.011(3) 0.007(3) 0.006(3) C19 0.057(5) 0.031(4) 0.027(4) 0.006(3) -0.004(4) 0.001(4) C20 0.063(6) 0.028(4) 0.027(4) 0.000(3) -0.002(4) 0.007(4) C21 0.036(4) 0.034(4) 0.027(4) 0.007(3) 0.001(3) 0.004(3) C22 0.043(5) 0.037(4) 0.032(4) 0.006(3) -0.004(3) 0.008(4) C23 0.052(5) 0.029(4) 0.031(4) 0.007(3) 0.009(4) 0.006(3) C24 0.040(4) 0.033(4) 0.021(3) 0.000(3) 0.002(3) 0.009(3) C25 0.030(4) 0.033(4) 0.028(4) 0.011(3) -0.003(3) 0.004(3) C26 0.035(4) 0.030(4) 0.029(4) 0.004(3) 0.003(3) 0.003(3) C27 0.049(5) 0.043(5) 0.033(4) -0.003(4) -0.010(4) 0.025(4) C28 0.068(6) 0.042(5) 0.033(4) -0.004(4) -0.012(4) 0.025(5) C29 0.034(5) 0.132(10) 0.029(4) 0.023(6) 0.003(4) 0.018(6) C30 0.030(5) 0.161(12) 0.027(4) 0.023(6) 0.005(4) 0.011(6) C31 0.026(4) 0.049(4) 0.021(3) 0.007(3) 0.001(3) 0.010(3) C32 0.031(4) 0.040(4) 0.019(3) 0.005(3) 0.003(3) 0.003(3) C33 0.026(3) 0.035(4) 0.028(4) 0.007(3) 0.006(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O2 2.243(5) 2_653 ? Cd1 O7 2.314(5) . ? Cd1 O1 2.331(5) . ? Cd1 O9 2.344(5) . ? Cd1 N1 2.355(6) . ? Cd1 O3 2.374(5) . ? Cd2 O5 2.251(5) 2_663 ? Cd2 N3 2.276(6) . ? Cd2 O4 2.354(5) . ? Cd2 O9 2.373(5) . ? Cd2 O10 2.492(6) . ? Cd2 O3 2.566(5) . ? Cd2 O6 2.571(6) 2_663 ? Cd2 C17 2.753(7) . ? Cd2 C9 2.758(7) 2_663 ? Cd3 O8 2.320(5) 2_563 ? Cd3 O8 2.320(5) . ? Cd3 O1W 2.336(6) . ? Cd3 O1W 2.336(6) 2_563 ? Cd3 N2 2.372(6) 2_552 ? Cd3 N2 2.372(6) 1_566 ? O1 C7 1.259(8) . ? O2 C7 1.260(8) . ? O2 Cd1 2.243(5) 2_653 ? O3 C8 1.265(8) . ? O4 C8 1.252(8) . ? O5 C9 1.245(9) . ? O5 Cd2 2.251(5) 2_663 ? O6 C9 1.254(9) . ? O6 Cd2 2.571(6) 2_663 ? O7 C16 1.275(9) . ? O8 C16 1.256(9) . ? O9 C17 1.257(9) . ? O10 C17 1.229(9) . ? O11 C18 1.224(10) . ? O12 C18 1.331(9) . ? N1 C19 1.349(10) . ? N1 C23 1.354(10) . ? N2 C28 1.332(10) . ? N2 C26 1.347(10) . ? N2 Cd3 2.372(6) 1_544 ? N3 C33 1.339(9) . ? N3 C29 1.341(11) . ? C1 C2 1.409(10) . ? C1 C6 1.422(9) . ? C1 C7 1.517(10) . ? C2 C3 1.389(12) . ? C3 C4 1.399(12) . ? C4 C5 1.392(10) . ? C5 C6 1.392(10) . ? C5 C9 1.515(10) . ? C6 C8 1.517(9) . ? C9 Cd2 2.758(7) 2_663 ? C10 C15 1.416(10) . ? C10 C11 1.418(9) . ? C10 C16 1.504(10) . ? C11 C12 1.399(10) . ? C11 C17 1.539(9) . ? C12 C13 1.405(11) . ? C12 C18 1.518(10) . ? C13 C14 1.403(13) . ? C14 C15 1.393(12) . ? C19 C20 1.396(11) . ? C20 C21 1.382(11) . ? C21 C22 1.401(11) . ? C21 C24 1.512(10) . ? C22 C23 1.381(11) . ? C24 C25 1.396(10) . ? C24 C27 1.401(11) . ? C25 C26 1.406(10) . ? C27 C28 1.381(11) . ? C29 C30 1.383(12) . ? C30 C31 1.375(11) . ? C31 C32 1.406(10) . ? C31 C31 1.505(13) 2_764 ? C32 C33 1.380(10) . ? 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 Cd1 O7 106.87(19) 2_653 . ? O2 Cd1 O1 93.26(18) 2_653 . ? O7 Cd1 O1 152.9(2) . . ? O2 Cd1 O9 87.8(2) 2_653 . ? O7 Cd1 O9 84.4(2) . . ? O1 Cd1 O9 78.33(18) . . ? O2 Cd1 N1 101.3(2) 2_653 . ? O7 Cd1 N1 95.2(2) . . ? O1 Cd1 N1 98.4(2) . . ? O9 Cd1 N1 170.5(2) . . ? O2 Cd1 O3 164.45(19) 2_653 . ? O7 Cd1 O3 76.78(19) . . ? O1 Cd1 O3 79.18(17) . . ? O9 Cd1 O3 77.37(18) . . ? N1 Cd1 O3 93.3(2) . . ? O5 Cd2 N3 129.5(2) 2_663 . ? O5 Cd2 O4 94.67(19) 2_663 . ? N3 Cd2 O4 82.9(2) . . ? O5 Cd2 O9 128.8(2) 2_663 . ? N3 Cd2 O9 99.8(2) . . ? O4 Cd2 O9 105.65(17) . . ? O5 Cd2 O10 93.5(2) 2_663 . ? N3 Cd2 O10 108.0(2) . . ? O4 Cd2 O10 157.10(18) . . ? O9 Cd2 O10 53.44(17) . . ? O5 Cd2 O3 82.99(17) 2_663 . ? N3 Cd2 O3 129.8(2) . . ? O4 Cd2 O3 53.73(16) . . ? O9 Cd2 O3 73.21(16) . . ? O10 Cd2 O3 106.31(17) . . ? O5 Cd2 O6 53.30(18) 2_663 2_663 ? N3 Cd2 O6 82.8(2) . 2_663 ? O4 Cd2 O6 116.6(2) . 2_663 ? O9 Cd2 O6 137.7(2) . 2_663 ? O10 Cd2 O6 85.3(2) . 2_663 ? O3 Cd2 O6 135.73(16) . 2_663 ? O5 Cd2 C17 110.7(2) 2_663 . ? N3 Cd2 C17 107.9(2) . . ? O4 Cd2 C17 131.51(19) . . ? O9 Cd2 C17 27.11(19) . . ? O10 Cd2 C17 26.51(19) . . ? O3 Cd2 C17 88.14(18) . . ? O6 Cd2 C17 111.7(2) 2_663 . ? O5 Cd2 C9 26.4(2) 2_663 2_663 ? N3 Cd2 C9 106.7(2) . 2_663 ? O4 Cd2 C9 106.9(2) . 2_663 ? O9 Cd2 C9 140.0(2) . 2_663 ? O10 Cd2 C9 89.6(2) . 2_663 ? O3 Cd2 C9 109.12(19) . 2_663 ? O6 Cd2 C9 26.92(19) 2_663 2_663 ? C17 Cd2 C9 114.1(2) . 2_663 ? O8 Cd3 O8 180.000(1) 2_563 . ? O8 Cd3 O1W 94.8(2) 2_563 . ? O8 Cd3 O1W 85.2(2) . . ? O8 Cd3 O1W 85.2(2) 2_563 2_563 ? O8 Cd3 O1W 94.8(2) . 2_563 ? O1W Cd3 O1W 180.0(3) . 2_563 ? O8 Cd3 N2 89.5(2) 2_563 2_552 ? O8 Cd3 N2 90.5(2) . 2_552 ? O1W Cd3 N2 86.6(2) . 2_552 ? O1W Cd3 N2 93.4(2) 2_563 2_552 ? O8 Cd3 N2 90.5(2) 2_563 1_566 ? O8 Cd3 N2 89.5(2) . 1_566 ? O1W Cd3 N2 93.4(2) . 1_566 ? O1W Cd3 N2 86.6(2) 2_563 1_566 ? N2 Cd3 N2 180.000(2) 2_552 1_566 ? C7 O1 Cd1 127.3(4) . . ? C7 O2 Cd1 118.8(4) . 2_653 ? C8 O3 Cd1 113.5(4) . . ? C8 O3 Cd2 85.2(4) . . ? Cd1 O3 Cd2 100.90(17) . . ? C8 O4 Cd2 95.2(4) . . ? C9 O5 Cd2 100.1(4) . 2_663 ? C9 O6 Cd2 84.9(4) . 2_663 ? C16 O7 Cd1 129.4(5) . . ? C16 O8 Cd3 138.5(5) . . ? C17 O9 Cd1 124.1(4) . . ? C17 O9 Cd2 93.5(4) . . ? Cd1 O9 Cd2 107.8(2) . . ? C17 O10 Cd2 88.6(4) . . ? C19 N1 C23 116.7(6) . . ? C19 N1 Cd1 120.4(5) . . ? C23 N1 Cd1 122.6(5) . . ? C28 N2 C26 116.6(7) . . ? C28 N2 Cd3 124.6(5) . 1_544 ? C26 N2 Cd3 118.7(5) . 1_544 ? C33 N3 C29 116.6(7) . . ? C33 N3 Cd2 121.3(5) . . ? C29 N3 Cd2 121.3(5) . . ? C2 C1 C6 118.4(7) . . ? C2 C1 C7 118.5(6) . . ? C6 C1 C7 122.9(6) . . ? C3 C2 C1 121.0(7) . . ? C2 C3 C4 120.2(7) . . ? C5 C4 C3 119.5(8) . . ? C6 C5 C4 121.1(7) . . ? C6 C5 C9 119.7(6) . . ? C4 C5 C9 119.2(7) . . ? C5 C6 C1 119.8(6) . . ? C5 C6 C8 121.2(6) . . ? C1 C6 C8 119.0(6) . . ? O1 C7 O2 124.4(7) . . ? O1 C7 C1 117.9(6) . . ? O2 C7 C1 117.6(6) . . ? O4 C8 O3 124.9(6) . . ? O4 C8 C6 119.2(6) . . ? O3 C8 C6 115.8(6) . . ? O5 C9 O6 121.7(7) . . ? O5 C9 C5 118.1(6) . . ? O6 C9 C5 120.1(6) . . ? O5 C9 Cd2 53.5(4) . 2_663 ? O6 C9 Cd2 68.2(4) . 2_663 ? C5 C9 Cd2 171.2(5) . 2_663 ? C15 C10 C11 119.6(7) . . ? C15 C10 C16 118.0(7) . . ? C11 C10 C16 122.3(6) . . ? C12 C11 C10 119.5(6) . . ? C12 C11 C17 123.7(6) . . ? C10 C11 C17 116.9(6) . . ? C11 C12 C13 120.6(7) . . ? C11 C12 C18 119.0(6) . . ? C13 C12 C18 120.4(7) . . ? C14 C13 C12 119.7(8) . . ? C15 C14 C13 120.5(9) . . ? C14 C15 C10 119.9(8) . . ? O8 C16 O7 124.4(7) . . ? O8 C16 C10 116.8(6) . . ? O7 C16 C10 118.8(6) . . ? O10 C17 O9 123.5(7) . . ? O10 C17 C11 119.8(6) . . ? O9 C17 C11 116.6(6) . . ? O10 C17 Cd2 64.9(4) . . ? O9 C17 Cd2 59.4(4) . . ? C11 C17 Cd2 167.4(5) . . ? O11 C18 O12 124.1(7) . . ? O11 C18 C12 122.8(7) . . ? O12 C18 C12 113.1(7) . . ? N1 C19 C20 122.7(8) . . ? C21 C20 C19 120.4(7) . . ? C20 C21 C22 116.6(7) . . ? C20 C21 C24 121.3(7) . . ? C22 C21 C24 122.1(7) . . ? C23 C22 C21 120.1(8) . . ? N1 C23 C22 123.2(7) . . ? C25 C24 C27 116.7(7) . . ? C25 C24 C21 120.3(7) . . ? C27 C24 C21 123.0(7) . . ? C24 C25 C26 118.6(7) . . ? N2 C26 C25 124.0(7) . . ? C28 C27 C24 120.5(7) . . ? N2 C28 C27 123.6(8) . . ? N3 C29 C30 123.1(8) . . ? C31 C30 C29 120.6(8) . . ? C30 C31 C32 116.5(7) . . ? C30 C31 C31 122.3(9) . 2_764 ? C32 C31 C31 121.2(8) . 2_764 ? C33 C32 C31 119.4(7) . . ? N3 C33 C32 123.7(7) . . ? 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 O12 H12A O6 0.82 1.78 2.601(8) 176.5 1_556 O1W H1WA O4 1.08(12) 1.86(12) 2.880(8) 156(9) 2_663 O1W H1WB O7 0.77(8) 2.45(9) 3.064(9) 139(8) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.677 _refine_diff_density_min -2.788 _refine_diff_density_rms 0.201 data_13 _database_code_depnum_ccdc_archive 'CCDC 701828' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 N2 O6' _chemical_formula_weight 365.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.141(3) _cell_length_b 7.8241(10) _cell_length_c 19.886(2) _cell_angle_alpha 90.00 _cell_angle_beta 126.979(2) _cell_angle_gamma 90.00 _cell_volume 3249.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3242 _cell_measurement_theta_min 2.506 _cell_measurement_theta_max 27.00 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details SADABS _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8254 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3489 _reflns_number_gt 2990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0893P)^2^+1.8465P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3489 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 O1 O 0.05783(5) 0.45611(15) 0.30474(7) 0.0308(3) Uani 1 1 d . . . H1 H 0.0000 0.463(6) 0.2500 0.084(13) Uiso 1 2 d S . . O2 O 0.15318(6) 0.50985(18) 0.33859(8) 0.0379(3) Uani 1 1 d . . . O3 O 0.00441(7) 0.62562(17) 0.04010(7) 0.0448(4) Uani 1 1 d . . . H3 H 0.0000 0.5000 0.0000 0.118(18) Uiso 1 2 d S . . O4 O 0.03856(8) 0.44560(16) 0.14510(8) 0.0466(4) Uani 1 1 d . . . O5 O 0.16529(9) 0.9779(2) 0.44648(9) 0.0693(5) Uani 1 1 d . . . O6 O 0.11438(7) 0.73642(19) 0.42991(8) 0.0443(4) Uani 1 1 d . . . H6 H 0.1330(15) 0.742(4) 0.486(2) 0.096(11) Uiso 1 1 d . . . C1 C 0.07486(7) 0.7225(2) 0.25853(9) 0.0248(3) Uani 1 1 d . . . C2 C 0.04323(7) 0.7420(2) 0.17195(9) 0.0266(3) Uani 1 1 d . . . C3 C 0.02772(9) 0.9051(2) 0.13664(11) 0.0353(4) Uani 1 1 d . . . H3A H 0.0060 0.9172 0.0789 0.042 Uiso 1 1 calc R . . C4 C 0.04409(10) 1.0485(2) 0.18586(13) 0.0430(5) Uani 1 1 d . . . H4A H 0.0331 1.1567 0.1616 0.052 Uiso 1 1 calc R . . C5 C 0.07680(9) 1.0302(2) 0.27135(12) 0.0396(4) Uani 1 1 d . . . H5A H 0.0888 1.1270 0.3049 0.048 Uiso 1 1 calc R . . C6 C 0.09211(8) 0.8694(2) 0.30833(10) 0.0311(4) Uani 1 1 d . . . C7 C 0.02758(8) 0.5898(2) 0.11672(9) 0.0277(3) Uani 1 1 d . . . C8 C 0.09718(7) 0.5498(2) 0.30184(9) 0.0255(3) Uani 1 1 d . . . C9 C 0.12788(9) 0.8658(2) 0.40196(11) 0.0365(4) Uani 1 1 d . . . N1 N 0.36333(8) 0.1494(2) 0.52915(9) 0.0438(4) Uani 1 1 d . . . N2 N 0.17151(8) 0.2476(2) 0.09182(9) 0.0412(4) Uani 1 1 d . . . C10 C 0.29983(11) 0.1255(3) 0.48444(12) 0.0468(5) Uani 1 1 d . . . H10A H 0.2825 0.0878 0.5112 0.056 Uiso 1 1 calc R . . C11 C 0.26053(10) 0.1564(3) 0.39955(11) 0.0429(5) Uani 1 1 d . . . H11A H 0.2166 0.1406 0.3688 0.051 Uiso 1 1 calc R . . C12 C 0.28641(9) 0.2114(2) 0.35953(10) 0.0355(4) Uani 1 1 d . . . C13 C 0.35223(10) 0.2407(3) 0.40886(12) 0.0444(5) Uani 1 1 d . . . H13A H 0.3707 0.2833 0.3844 0.053 Uiso 1 1 calc R . . C14 C 0.38977(10) 0.2065(3) 0.49373(12) 0.0470(5) Uani 1 1 d . . . H14A H 0.4338 0.2234 0.5264 0.056 Uiso 1 1 calc R . . C15 C 0.14634(9) 0.2792(3) 0.13227(11) 0.0414(5) Uani 1 1 d . . . H15A H 0.1032 0.3076 0.1009 0.050 Uiso 1 1 calc R . . C16 C 0.18202(9) 0.2714(3) 0.21932(11) 0.0386(4) Uani 1 1 d . . . H16A H 0.1629 0.2939 0.2455 0.046 Uiso 1 1 calc R . . C17 C 0.24631(8) 0.2297(2) 0.26664(10) 0.0332(4) Uani 1 1 d . . . C18 C 0.27195(9) 0.1975(3) 0.22398(11) 0.0431(5) Uani 1 1 d . . . H18A H 0.3150 0.1695 0.2536 0.052 Uiso 1 1 calc R . . C19 C 0.23324(10) 0.2073(3) 0.13741(12) 0.0462(5) Uani 1 1 d . . . H19A H 0.2511 0.1848 0.1096 0.055 Uiso 1 1 calc 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 O1 0.0276(6) 0.0366(7) 0.0223(5) 0.0063(5) 0.0120(5) -0.0008(5) O2 0.0295(6) 0.0475(8) 0.0335(6) 0.0097(5) 0.0173(5) 0.0076(5) O3 0.0664(9) 0.0395(7) 0.0204(6) 0.0014(5) 0.0218(6) 0.0074(6) O4 0.0797(10) 0.0286(7) 0.0307(7) 0.0011(5) 0.0328(7) 0.0038(6) O5 0.0886(13) 0.0633(11) 0.0336(8) -0.0172(7) 0.0247(8) -0.0354(9) O6 0.0538(8) 0.0522(9) 0.0222(6) -0.0072(6) 0.0203(6) -0.0125(6) C1 0.0237(7) 0.0289(8) 0.0219(7) -0.0005(6) 0.0138(6) -0.0007(6) C2 0.0289(8) 0.0283(8) 0.0216(8) 0.0013(6) 0.0147(6) 0.0005(6) C3 0.0419(10) 0.0332(9) 0.0260(8) 0.0054(7) 0.0178(7) 0.0025(7) C4 0.0522(11) 0.0281(9) 0.0402(10) 0.0062(8) 0.0233(9) 0.0025(8) C5 0.0460(10) 0.0287(9) 0.0369(9) -0.0068(7) 0.0211(8) -0.0033(8) C6 0.0332(8) 0.0328(9) 0.0259(8) -0.0034(6) 0.0170(7) -0.0021(7) C7 0.0287(8) 0.0317(8) 0.0208(7) 0.0008(6) 0.0139(6) 0.0017(6) C8 0.0278(8) 0.0303(8) 0.0164(6) -0.0008(6) 0.0122(6) 0.0006(6) C9 0.0400(9) 0.0384(9) 0.0272(8) -0.0082(7) 0.0182(8) -0.0037(8) N1 0.0538(10) 0.0425(9) 0.0235(7) 0.0028(6) 0.0171(7) 0.0096(8) N2 0.0410(9) 0.0552(10) 0.0225(7) 0.0058(6) 0.0166(7) 0.0110(7) C10 0.0602(13) 0.0534(12) 0.0323(9) 0.0076(9) 0.0307(9) 0.0072(10) C11 0.0412(10) 0.0568(12) 0.0292(9) 0.0060(8) 0.0203(8) 0.0056(9) C12 0.0371(9) 0.0428(10) 0.0241(8) 0.0046(7) 0.0170(7) 0.0088(7) C13 0.0391(10) 0.0604(13) 0.0280(9) 0.0042(8) 0.0171(8) 0.0033(9) C14 0.0402(10) 0.0566(13) 0.0279(9) 0.0004(8) 0.0118(8) 0.0043(9) C15 0.0339(9) 0.0570(12) 0.0281(9) 0.0070(8) 0.0159(8) 0.0119(8) C16 0.0369(9) 0.0537(11) 0.0268(8) 0.0047(8) 0.0201(8) 0.0098(8) C17 0.0328(9) 0.0417(10) 0.0222(8) 0.0040(7) 0.0150(7) 0.0056(7) C18 0.0330(9) 0.0669(13) 0.0274(9) 0.0088(9) 0.0170(7) 0.0143(9) C19 0.0442(11) 0.0700(14) 0.0295(9) 0.0069(9) 0.0248(8) 0.0144(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.292(2) . ? O1 H1 1.222(2) . ? O2 C8 1.2197(19) . ? O3 C7 1.2871(19) . ? O3 H3 1.2266(13) . ? O4 C7 1.216(2) . ? O5 C9 1.212(2) . ? O6 C9 1.302(2) . ? O6 H6 0.90(4) . ? C1 C2 1.399(2) . ? C1 C6 1.403(2) . ? C1 C8 1.518(2) . ? C2 C3 1.394(2) . ? C2 C7 1.500(2) . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 C5 1.376(3) . ? C4 H4A 0.9300 . ? C5 C6 1.389(3) . ? C5 H5A 0.9300 . ? C6 C9 1.499(2) . ? N1 C14 1.326(3) . ? N1 C10 1.344(3) . ? N2 C19 1.329(2) . ? N2 C15 1.333(2) . ? C10 C11 1.370(3) . ? C10 H10A 0.9300 . ? C11 C12 1.387(3) . ? C11 H11A 0.9300 . ? C12 C13 1.395(3) . ? C12 C17 1.484(2) . ? C13 C14 1.375(3) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.388(2) . ? C15 H15A 0.9300 . ? C16 C17 1.383(2) . ? C16 H16A 0.9300 . ? C17 C18 1.384(3) . ? C18 C19 1.378(3) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 H1 121.7(15) . . ? C7 O3 H3 112.85(12) . . ? C9 O6 H6 114(2) . . ? C2 C1 C6 118.71(14) . . ? C2 C1 C8 122.41(13) . . ? C6 C1 C8 118.57(13) . . ? C3 C2 C1 119.80(14) . . ? C3 C2 C7 119.28(13) . . ? C1 C2 C7 120.89(14) . . ? C4 C3 C2 121.06(15) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 119.33(16) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 121.03(16) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C5 C6 C1 120.03(15) . . ? C5 C6 C9 116.11(15) . . ? C1 C6 C9 123.85(15) . . ? O4 C7 O3 124.26(15) . . ? O4 C7 C2 120.81(14) . . ? O3 C7 C2 114.89(14) . . ? O2 C8 O1 121.92(15) . . ? O2 C8 C1 118.76(14) . . ? O1 C8 C1 119.05(13) . . ? O5 C9 O6 123.91(16) . . ? O5 C9 C6 121.36(17) . . ? O6 C9 C6 114.72(15) . . ? C14 N1 C10 121.77(16) . . ? C19 N2 C15 118.02(15) . . ? N1 C10 C11 120.19(19) . . ? N1 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C10 C11 C12 119.92(19) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C13 117.95(16) . . ? C11 C12 C17 121.41(17) . . ? C13 C12 C17 120.56(16) . . ? C14 C13 C12 119.93(19) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? N1 C14 C13 120.15(19) . . ? N1 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? N2 C15 C16 122.60(17) . . ? N2 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C17 C16 C15 119.27(16) . . ? C17 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? C16 C17 C18 117.63(15) . . ? C16 C17 C12 121.95(16) . . ? C18 C17 C12 120.36(16) . . ? C19 C18 C17 119.56(17) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? N2 C19 C18 122.93(17) . . ? N2 C19 H19A 118.5 . . ? C18 C19 H19A 118.5 . . ? 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 O3 H3 O3 1.2266(13) 1.2266(13) 2.453(3) 180.00(14) 5_565 O3 H3 O4 1.2266(13) 2.4543(13) 3.1872(17) 115.90(7) 5_565 O6 H6 N2 0.90(4) 1.71(4) 2.6129(19) 178(3) 6_566 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.468 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.119 #=================================================END