# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Raju Mondal' _publ_contact_author_email icrm@iacs.res.in _publ_author_name 'Raju Mondal' data_10ag15_0m _database_code_depnum_ccdc_archive 'CCDC 790289' #TrackingRef '- DPA_Co.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H24 N4 O5 Co, 2 H2O' _chemical_formula_sum 'C25 H28 Co N4 O6' _chemical_formula_weight 539.44 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 Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.9833(7) _cell_length_b 25.7855(14) _cell_length_c 30.5266(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10219.7(10) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2950 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.12 _exptl_crystal_description Prism _exptl_crystal_colour Purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4496 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.761199 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0589 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34583 _diffrn_reflns_av_R_equivalents 0.1117 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.46 _reflns_number_total 2369 _reflns_number_gt 1611 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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. Water hydrogen atoms were not able to be located in the difference map. ; _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^)+(0.0890P)^2^+22.2887P] 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 2369 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.013 _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 0.6250 0.22534(3) 0.1250 0.0423(3) Uani 1 2 d S . . N1 N 0.5139(2) 0.26970(12) 0.10082(10) 0.0428(8) Uani 1 1 d . . . O1 O 0.6836(2) 0.18313(12) 0.07966(10) 0.0644(9) Uani 1 1 d . . . C1 C 0.5121(3) 0.30992(15) 0.07259(12) 0.0447(9) Uani 1 1 d . . . O1W O 1.0767(3) 0.17360(15) 0.08198(14) 0.0991(13) Uani 1 1 d . . . N2 N 0.4151(2) 0.26432(12) 0.11490(10) 0.0430(8) Uani 1 1 d . . . H2A H 0.3952 0.2412 0.1333 0.052 Uiso 1 1 calc R . . O2 O 0.8544(2) 0.17854(12) 0.08152(10) 0.0625(8) Uani 1 1 d . . . C2 C 0.4128(3) 0.33013(15) 0.06924(12) 0.0432(9) Uani 1 1 d . . . C3 C 0.3526(3) 0.29927(15) 0.09670(12) 0.0450(9) Uani 1 1 d . . . C7 C 0.3750 0.3750 0.04243(18) 0.0479(13) Uani 1 2 d S . . H7A H 0.3195 0.3631 0.0237 0.072 Uiso 0.50 1 calc PR . . H7B H 0.4305 0.3869 0.0237 0.072 Uiso 0.50 1 calc PR . . C8 C 0.6098(3) 0.32515(18) 0.04983(16) 0.0632(12) Uani 1 1 d . . . H8A H 0.6651 0.3034 0.0597 0.095 Uiso 1 1 calc R . . H8B H 0.6256 0.3607 0.0564 0.095 Uiso 1 1 calc R . . H8C H 0.6014 0.3212 0.0188 0.095 Uiso 1 1 calc R . . C9 C 0.2405(3) 0.30145(19) 0.10694(15) 0.0615(12) Uani 1 1 d . . . H9A H 0.2194 0.2693 0.1200 0.092 Uiso 1 1 calc R . . H9B H 0.2024 0.3071 0.0804 0.092 Uiso 1 1 calc R . . H9C H 0.2276 0.3294 0.1270 0.092 Uiso 1 1 calc R . . C12 C 0.7688(3) 0.16308(16) 0.06901(13) 0.0499(10) Uani 1 1 d . . . C13 C 0.7611(3) 0.11742(16) 0.03784(13) 0.0506(10) Uani 1 1 d . . . C14 C 0.6711(4) 0.10815(15) 0.01283(12) 0.0524(11) Uani 1 1 d . . . C15 C 0.6716(4) 0.06510(18) -0.01482(14) 0.0671(13) Uani 1 1 d . . . H15A H 0.6142 0.0585 -0.0322 0.081 Uiso 1 1 calc R . . C16 C 0.7553(5) 0.03201(19) -0.01709(16) 0.0762(16) Uani 1 1 d . . . H16A H 0.7535 0.0035 -0.0357 0.091 Uiso 1 1 calc R . . C17 C 0.8413(5) 0.04121(19) 0.00813(16) 0.0688(14) Uani 1 1 d . . . H17A H 0.8971 0.0186 0.0070 0.083 Uiso 1 1 calc R . . C18 C 0.8442(4) 0.08437(16) 0.03528(15) 0.0594(12) Uani 1 1 d . . . H18A H 0.9028 0.0910 0.0519 0.071 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 0.0348(4) 0.0498(5) 0.0423(4) 0.000 0.0070(3) 0.000 N1 0.0333(17) 0.0532(19) 0.0419(18) 0.0024(16) 0.0073(13) 0.0018(14) O1 0.0429(17) 0.079(2) 0.071(2) -0.0342(17) 0.0032(15) 0.0060(15) C1 0.042(2) 0.049(2) 0.043(2) 0.0030(18) 0.0105(17) 0.0022(18) O1W 0.080(3) 0.095(3) 0.122(3) 0.030(2) -0.004(2) 0.009(2) N2 0.0330(16) 0.0530(18) 0.0431(17) 0.0077(14) 0.0055(14) -0.0019(14) O2 0.0477(19) 0.069(2) 0.070(2) -0.0146(16) 0.0021(15) 0.0036(15) C2 0.042(2) 0.051(2) 0.0370(19) -0.0029(17) 0.0034(17) 0.0014(18) C3 0.038(2) 0.054(2) 0.043(2) -0.0026(18) -0.0014(17) 0.0023(18) C7 0.050(3) 0.048(3) 0.047(3) 0.000 0.000 0.003(3) C8 0.050(3) 0.070(3) 0.070(3) 0.018(2) 0.019(2) 0.004(2) C9 0.038(2) 0.078(3) 0.068(3) 0.012(3) 0.000(2) 0.000(2) C12 0.053(3) 0.057(3) 0.039(2) 0.0005(18) 0.0077(19) 0.007(2) C13 0.062(3) 0.053(2) 0.037(2) 0.0060(18) 0.0146(19) 0.000(2) C14 0.078(3) 0.049(2) 0.0297(19) 0.0014(17) 0.0151(19) -0.004(2) C15 0.092(4) 0.061(3) 0.048(3) -0.006(2) 0.007(2) -0.001(3) C16 0.118(5) 0.060(3) 0.051(3) -0.007(2) 0.025(3) 0.002(3) C17 0.083(4) 0.061(3) 0.062(3) 0.013(2) 0.033(3) 0.012(3) C18 0.069(3) 0.054(3) 0.054(3) 0.004(2) 0.027(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 Co1 O1 1.918(3) . ? Co1 O1 1.918(3) 11_554 ? Co1 N1 1.983(3) 11_554 ? Co1 N1 1.983(3) . ? N1 C1 1.349(5) . ? N1 N2 1.361(4) . ? O1 C12 1.264(5) . ? C1 C2 1.394(5) . ? C1 C8 1.499(5) . ? N2 C3 1.334(5) . ? N2 H2A 0.8600 . ? O2 C12 1.240(5) . ? C2 C3 1.395(5) . ? C2 C7 1.500(5) . ? C3 C9 1.489(5) . ? C7 C2 1.500(5) 2 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 C13 1.517(6) . ? C13 C18 1.377(6) . ? C13 C14 1.416(6) . ? C14 C15 1.395(6) . ? C14 C14 1.480(9) 14_545 ? C15 C16 1.383(7) . ? C15 H15A 0.9300 . ? C16 C17 1.377(7) . ? C16 H16A 0.9300 . ? C17 C18 1.388(6) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 110.9(2) . 11_554 ? O1 Co1 N1 107.92(12) . 11_554 ? O1 Co1 N1 110.30(13) 11_554 11_554 ? O1 Co1 N1 110.30(13) . . ? O1 Co1 N1 107.92(12) 11_554 . ? N1 Co1 N1 109.55(18) 11_554 . ? C1 N1 N2 105.3(3) . . ? C1 N1 Co1 134.0(3) . . ? N2 N1 Co1 120.6(2) . . ? C12 O1 Co1 139.9(3) . . ? N1 C1 C2 110.5(3) . . ? N1 C1 C8 118.9(3) . . ? C2 C1 C8 130.6(4) . . ? C3 N2 N1 111.9(3) . . ? C3 N2 H2A 124.0 . . ? N1 N2 H2A 124.0 . . ? C1 C2 C3 105.1(3) . . ? C1 C2 C7 129.1(3) . . ? C3 C2 C7 125.8(3) . . ? N2 C3 C2 107.1(3) . . ? N2 C3 C9 122.2(4) . . ? C2 C3 C9 130.7(4) . . ? C2 C7 C2 113.8(4) . 2 ? C2 C7 H7A 108.8 . . ? C2 C7 H7A 108.8 2 . ? C2 C7 H7B 108.8 . . ? C2 C7 H7B 108.8 2 . ? H7A C7 H7B 107.7 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C12 O1 125.0(4) . . ? O2 C12 C13 120.1(4) . . ? O1 C12 C13 114.9(4) . . ? C18 C13 C14 120.7(4) . . ? C18 C13 C12 117.6(4) . . ? C14 C13 C12 121.6(4) . . ? C15 C14 C13 117.2(4) . . ? C15 C14 C14 118.1(4) . 14_545 ? C13 C14 C14 124.7(4) . 14_545 ? C16 C15 C14 121.7(5) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? C17 C16 C15 120.2(5) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 C18 119.6(5) . . ? C16 C17 H17A 120.2 . . ? C18 C17 H17A 120.2 . . ? C13 C18 C17 120.6(5) . . ? C13 C18 H18A 119.7 . . ? C17 C18 H18A 119.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.615 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.070 # Attachment '- DPA_Zn.cif' data_07rmd014_0m _database_code_depnum_ccdc_archive 'CCDC 790290' #TrackingRef '- DPA_Zn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H24 N4 O5 Zn, 2 H2O' _chemical_formula_sum 'C25 H28 N4 O6 Zn' _chemical_formula_weight 545.88 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fddd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+3/4, -y+3/4, z' '-x+3/4, y, -z+3/4' 'x, -y+3/4, -z+3/4' 'x, y+1/2, z+1/2' '-x+3/4, -y+5/4, z+1/2' '-x+3/4, y+1/2, -z+5/4' 'x, -y+5/4, -z+5/4' 'x+1/2, y, z+1/2' '-x+5/4, -y+3/4, z+1/2' '-x+5/4, y, -z+5/4' 'x+1/2, -y+3/4, -z+5/4' 'x+1/2, y+1/2, z' '-x+5/4, -y+5/4, z' '-x+5/4, y+1/2, -z+3/4' 'x+1/2, -y+5/4, -z+3/4' '-x, -y, -z' 'x-3/4, y-3/4, -z' 'x-3/4, -y, z-3/4' '-x, y-3/4, z-3/4' '-x, -y+1/2, -z+1/2' 'x-3/4, y-1/4, -z+1/2' 'x-3/4, -y+1/2, z-1/4' '-x, y-1/4, z-1/4' '-x+1/2, -y, -z+1/2' 'x-1/4, y-3/4, -z+1/2' 'x-1/4, -y, z-1/4' '-x+1/2, y-3/4, z-1/4' '-x+1/2, -y+1/2, -z' 'x-1/4, y-1/4, -z' 'x-1/4, -y+1/2, z-3/4' '-x+1/2, y-1/4, z-3/4' _cell_length_a 12.9600(10) _cell_length_b 25.619(2) _cell_length_c 30.850(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10242.7(14) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5688 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.1 _exptl_crystal_description Cube _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4544 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.859717 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0488 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32409 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.35 _reflns_number_total 2098 _reflns_number_gt 1699 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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. Water hydrogen atoms were not able to be located in the difference map. ; _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^)+(0.0681P)^2^+37.2762P] 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 2098 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.066 _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 Zn1 Zn 0.6250 0.225738(19) 0.1250 0.0362(2) Uani 1 2 d S . . N1 N 0.51343(19) 0.26950(10) 0.10044(9) 0.0359(6) Uani 1 1 d . . . O1 O 0.6826(2) 0.18355(11) 0.08058(9) 0.0648(8) Uani 1 1 d . . . C1 C 0.5123(2) 0.30933(12) 0.07218(11) 0.0371(8) Uani 1 1 d . . . O1W O 1.0755(4) 0.17408(17) 0.08229(17) 0.1279(17) Uani 1 1 d . . . N2 N 0.4159(2) 0.26441(11) 0.11486(9) 0.0373(7) Uani 1 1 d D . . H222 H 0.399(3) 0.2422(13) 0.1345(10) 0.059(12) Uiso 1 1 d D . . O2 O 0.8515(2) 0.17952(11) 0.08205(11) 0.0670(9) Uani 1 1 d . . . C2 C 0.4125(2) 0.32973(12) 0.06915(10) 0.0345(7) Uani 1 1 d . . . C3 C 0.3537(2) 0.29943(13) 0.09693(11) 0.0382(8) Uani 1 1 d . . . C7 C 0.3750 0.3750 0.04221(15) 0.0405(11) Uani 1 2 d S . . H7A H 0.4308 0.3868 0.0237 0.061 Uiso 0.50 1 calc PR . . H7B H 0.3192 0.3632 0.0237 0.061 Uiso 0.50 1 calc PR . . C8 C 0.6087(3) 0.32403(16) 0.04905(15) 0.0588(11) Uani 1 1 d . . . H8A H 0.6465 0.2931 0.0417 0.088 Uiso 1 1 calc R . . H8B H 0.6502 0.3458 0.0675 0.088 Uiso 1 1 calc R . . H8C H 0.5916 0.3428 0.0231 0.088 Uiso 1 1 calc R . . C9 C 0.2422(3) 0.30141(17) 0.10727(15) 0.0617(12) Uani 1 1 d . . . H9A H 0.2242 0.2720 0.1250 0.092 Uiso 1 1 calc R . . H9B H 0.2030 0.3003 0.0809 0.092 Uiso 1 1 calc R . . H9C H 0.2272 0.3331 0.1226 0.092 Uiso 1 1 calc R . . C12 C 0.7665(3) 0.16369(13) 0.06960(11) 0.0411(8) Uani 1 1 d . . . C13 C 0.7604(3) 0.11840(12) 0.03884(11) 0.0380(8) Uani 1 1 d . . . C14 C 0.6725(3) 0.10817(13) 0.01421(11) 0.0414(8) Uani 1 1 d . . . C15 C 0.6742(4) 0.06540(15) -0.01392(13) 0.0584(10) Uani 1 1 d . . . H15A H 0.6174 0.0587 -0.0315 0.070 Uiso 1 1 calc R . . C16 C 0.7590(4) 0.03292(16) -0.01599(15) 0.0684(13) Uani 1 1 d . . . H16A H 0.7585 0.0044 -0.0346 0.082 Uiso 1 1 calc R . . C17 C 0.8432(4) 0.04239(15) 0.00903(14) 0.0585(11) Uani 1 1 d . . . H17A H 0.8996 0.0200 0.0080 0.070 Uiso 1 1 calc R . . C18 C 0.8448(3) 0.08531(14) 0.03604(12) 0.0472(9) Uani 1 1 d . . . H18A H 0.9033 0.0921 0.0526 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 Zn1 0.0239(3) 0.0334(3) 0.0512(4) 0.000 0.0062(2) 0.000 N1 0.0237(13) 0.0355(14) 0.0484(17) 0.0054(13) 0.0084(12) 0.0041(11) O1 0.0360(15) 0.0806(19) 0.078(2) -0.0431(16) -0.0043(14) 0.0176(14) C1 0.0312(17) 0.0338(16) 0.046(2) 0.0024(15) 0.0085(15) 0.0035(14) O1W 0.094(3) 0.105(3) 0.185(5) 0.034(3) -0.012(3) 0.016(3) N2 0.0237(14) 0.0423(15) 0.0460(17) 0.0092(13) 0.0058(13) -0.0001(12) O2 0.0378(16) 0.0701(19) 0.093(2) -0.0344(17) -0.0023(15) 0.0038(13) C2 0.0302(17) 0.0357(16) 0.0376(18) -0.0007(14) 0.0047(14) 0.0060(13) C3 0.0273(18) 0.0435(19) 0.044(2) -0.0006(15) 0.0035(14) 0.0068(14) C7 0.046(3) 0.039(2) 0.036(3) 0.000 0.000 0.010(2) C8 0.039(2) 0.054(2) 0.083(3) 0.020(2) 0.026(2) 0.0069(17) C9 0.0279(19) 0.074(3) 0.083(3) 0.020(2) 0.007(2) 0.0085(19) C12 0.042(2) 0.0401(18) 0.041(2) -0.0014(15) 0.0034(16) 0.0046(16) C13 0.042(2) 0.0362(17) 0.0355(18) 0.0034(14) 0.0144(15) 0.0027(15) C14 0.051(2) 0.0398(18) 0.0340(18) 0.0025(14) 0.0086(16) 0.0011(15) C15 0.073(3) 0.053(2) 0.049(2) -0.0126(18) 0.001(2) -0.002(2) C16 0.098(4) 0.048(2) 0.059(3) -0.015(2) 0.022(3) 0.004(2) C17 0.069(3) 0.046(2) 0.060(3) 0.0043(19) 0.028(2) 0.016(2) C18 0.043(2) 0.0447(19) 0.054(2) 0.0041(17) 0.0170(18) 0.0097(16) _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 Zn1 O1 1.898(2) 11_554 ? Zn1 O1 1.898(2) . ? Zn1 N1 1.980(3) 11_554 ? Zn1 N1 1.980(3) . ? N1 C1 1.342(4) . ? N1 N2 1.347(4) . ? O1 C12 1.247(4) . ? C1 C2 1.398(4) . ? C1 C8 1.487(5) . ? N2 C3 1.327(4) . ? N2 H222 0.858(19) . ? O2 C12 1.235(4) . ? C2 C3 1.385(5) . ? C2 C7 1.507(4) . ? C3 C9 1.480(5) . ? C7 C2 1.507(4) 2 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 C13 1.501(5) . ? C13 C18 1.387(5) . ? C13 C14 1.394(5) . ? C14 C15 1.398(5) . ? C14 C14 1.503(7) 14_545 ? C15 C16 1.380(6) . ? C15 H15A 0.9300 . ? C16 C17 1.358(6) . ? C16 H16A 0.9300 . ? C17 C18 1.380(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 110.6(2) 11_554 . ? O1 Zn1 N1 109.45(12) 11_554 11_554 ? O1 Zn1 N1 108.16(11) . 11_554 ? O1 Zn1 N1 108.16(11) 11_554 . ? O1 Zn1 N1 109.45(12) . . ? N1 Zn1 N1 111.04(15) 11_554 . ? C1 N1 N2 106.1(3) . . ? C1 N1 Zn1 133.4(2) . . ? N2 N1 Zn1 120.3(2) . . ? C12 O1 Zn1 140.4(3) . . ? N1 C1 C2 109.7(3) . . ? N1 C1 C8 119.7(3) . . ? C2 C1 C8 130.6(3) . . ? C3 N2 N1 111.5(3) . . ? C3 N2 H222 126(3) . . ? N1 N2 H222 122(3) . . ? C3 C2 C1 105.0(3) . . ? C3 C2 C7 126.5(3) . . ? C1 C2 C7 128.5(3) . . ? N2 C3 C2 107.6(3) . . ? N2 C3 C9 121.7(3) . . ? C2 C3 C9 130.6(3) . . ? C2 C7 C2 113.1(4) 2 . ? C2 C7 H7A 109.0 2 . ? C2 C7 H7A 109.0 . . ? C2 C7 H7B 109.0 2 . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C12 O1 124.0(3) . . ? O2 C12 C13 119.8(3) . . ? O1 C12 C13 116.2(3) . . ? C18 C13 C14 119.7(3) . . ? C18 C13 C12 118.0(3) . . ? C14 C13 C12 122.2(3) . . ? C13 C14 C15 118.2(4) . . ? C13 C14 C14 124.2(3) . 14_545 ? C15 C14 C14 117.5(4) . 14_545 ? C16 C15 C14 120.9(4) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C17 C18 C13 120.8(4) . . ? C17 C18 H18A 119.6 . . ? C13 C18 H18A 119.6 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.719 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.068 # Attachment '- OBA_Cd.cif' data_10sd005_1_0m _database_code_depnum_ccdc_archive 'CCDC 790291' #TrackingRef '- OBA_Cd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Cd N4 O5' _chemical_formula_weight 572.88 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 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 9.6988(6) _cell_length_b 15.9616(10) _cell_length_c 15.1735(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.865(2) _cell_angle_gamma 90.00 _cell_volume 2320.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4113 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 26.7 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.737707 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0508 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 26189 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 24.87 _reflns_number_total 4024 _reflns_number_gt 3079 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0334P)^2^+0.5128P] 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 4024 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _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 0.13075(2) 0.422630(17) 0.595764(16) 0.04097(10) Uani 1 1 d . . . N1 N -0.0589(3) 0.33640(18) 0.55641(18) 0.0410(7) Uani 1 1 d . . . C1 C -0.1399(3) 0.2864(2) 0.5975(2) 0.0402(8) Uani 1 1 d . . . O1 O 0.0566(3) 0.46440(17) 1.42176(17) 0.0591(7) Uani 1 1 d . . . N2 N -0.1265(3) 0.3432(2) 0.4721(2) 0.0430(8) Uani 1 1 d . . . H222 H -0.101(4) 0.375(2) 0.440(3) 0.051(13) Uiso 1 1 d . . . C2 C -0.2613(3) 0.2635(2) 0.5395(2) 0.0365(8) Uani 1 1 d . . . O2 O 0.2652(3) 0.48256(17) 1.50210(17) 0.0612(8) Uani 1 1 d . . . O3 O 0.1806(3) 0.39627(19) 0.75821(17) 0.0603(7) Uani 1 1 d . . . C3 C -0.2473(3) 0.3011(2) 0.4591(2) 0.0408(8) Uani 1 1 d . . . N3 N -0.6995(3) 0.31505(18) 0.60411(18) 0.0424(7) Uani 1 1 d . . . O4 O 0.2090(3) 0.5226(2) 0.70589(17) 0.0684(8) Uani 1 1 d . . . C4 C -0.5178(3) 0.2491(2) 0.6844(2) 0.0408(8) Uani 1 1 d . . . N4 N -0.6392(3) 0.28946(19) 0.6861(2) 0.0430(7) Uani 1 1 d . . . H444 H -0.674(3) 0.305(2) 0.732(2) 0.042(10) Uiso 1 1 d . . . C5 C -0.4968(3) 0.2471(2) 0.5969(2) 0.0363(8) Uani 1 1 d . . . O5 O 0.4003(3) 0.58556(17) 1.12086(15) 0.0595(7) Uani 1 1 d . . . C6 C -0.6134(3) 0.2881(2) 0.5490(2) 0.0390(8) Uani 1 1 d . . . C7 C -0.3775(3) 0.2067(2) 0.5593(2) 0.0406(8) Uani 1 1 d . . . H7A H -0.4157 0.1783 0.5045 0.049 Uiso 1 1 calc R . . H7B H -0.3368 0.1643 0.6011 0.049 Uiso 1 1 calc R . . C8 C -0.0956(4) 0.2620(3) 0.6924(2) 0.0671(12) Uani 1 1 d . . . H8A H 0.0006 0.2768 0.7104 0.101 Uiso 1 1 calc R . . H8B H -0.1067 0.2026 0.6987 0.101 Uiso 1 1 calc R . . H8C H -0.1521 0.2909 0.7293 0.101 Uiso 1 1 calc R . . C9 C -0.3357(4) 0.3007(3) 0.3696(2) 0.0607(11) Uani 1 1 d . . . H9A H -0.2772 0.3052 0.3242 0.091 Uiso 1 1 calc R . . H9B H -0.3990 0.3473 0.3652 0.091 Uiso 1 1 calc R . . H9C H -0.3877 0.2494 0.3618 0.091 Uiso 1 1 calc R . . C10 C -0.4379(4) 0.2141(3) 0.7683(2) 0.0632(11) Uani 1 1 d . . . H10A H -0.4139 0.2586 0.8105 0.095 Uiso 1 1 calc R . . H10B H -0.3543 0.1878 0.7554 0.095 Uiso 1 1 calc R . . H10C H -0.4943 0.1735 0.7930 0.095 Uiso 1 1 calc R . . C11 C -0.6525(4) 0.2984(3) 0.4513(2) 0.0614(11) Uani 1 1 d . . . H11A H -0.7500 0.3116 0.4375 0.092 Uiso 1 1 calc R . . H11B H -0.6340 0.2473 0.4219 0.092 Uiso 1 1 calc R . . H11C H -0.5987 0.3431 0.4311 0.092 Uiso 1 1 calc R . . C12 C 0.2417(3) 0.5085(2) 1.3460(2) 0.0395(8) Uani 1 1 d . . . C13 C 0.3830(4) 0.5239(2) 1.3494(2) 0.0459(9) Uani 1 1 d . . . H13A H 0.4434 0.5192 1.4030 0.055 Uiso 1 1 calc R . . C14 C 0.4335(4) 0.5463(2) 1.2721(2) 0.0470(9) Uani 1 1 d . . . H14A H 0.5286 0.5555 1.2737 0.056 Uiso 1 1 calc R . . C15 C 0.3442(4) 0.5549(2) 1.1934(2) 0.0444(9) Uani 1 1 d . . . C16 C 0.2036(4) 0.5388(3) 1.1890(2) 0.0503(10) Uani 1 1 d . . . H16A H 0.1434 0.5438 1.1353 0.060 Uiso 1 1 calc R . . C17 C 0.1539(4) 0.5150(2) 1.2658(2) 0.0483(9) Uani 1 1 d . . . H17A H 0.0595 0.5031 1.2633 0.058 Uiso 1 1 calc R . . C18 C 0.3509(4) 0.5561(2) 1.0361(2) 0.0461(9) Uani 1 1 d . . . C19 C 0.3383(4) 0.6136(2) 0.9675(2) 0.0540(10) Uani 1 1 d . . . H19A H 0.3591 0.6698 0.9788 0.065 Uiso 1 1 calc R . . C20 C 0.2938(4) 0.5857(2) 0.8808(2) 0.0529(10) Uani 1 1 d . . . H20A H 0.2856 0.6237 0.8339 0.063 Uiso 1 1 calc R . . C21 C 0.2616(3) 0.5024(2) 0.8632(2) 0.0441(9) Uani 1 1 d . . . C22 C 0.2798(4) 0.4462(2) 0.9330(2) 0.0515(10) Uani 1 1 d . . . H22A H 0.2623 0.3897 0.9218 0.062 Uiso 1 1 calc R . . C23 C 0.3239(4) 0.4729(2) 1.0197(2) 0.0501(10) Uani 1 1 d . . . H23A H 0.3350 0.4345 1.0664 0.060 Uiso 1 1 calc R . . C24 C 0.1844(4) 0.4836(2) 1.4291(3) 0.0483(10) Uani 1 1 d . . . C25 C 0.2143(4) 0.4718(3) 0.7690(3) 0.0532(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.03573(15) 0.05616(18) 0.03216(15) -0.00303(13) 0.00880(10) -0.00076(13) N1 0.0360(16) 0.0514(19) 0.0354(17) -0.0014(14) 0.0046(13) -0.0020(14) C1 0.039(2) 0.047(2) 0.037(2) -0.0016(16) 0.0124(16) 0.0004(17) O1 0.0649(19) 0.0608(17) 0.0614(18) -0.0022(14) 0.0404(15) -0.0062(15) N2 0.0422(18) 0.055(2) 0.0337(18) 0.0028(16) 0.0123(14) -0.0029(15) C2 0.0347(18) 0.040(2) 0.0358(19) -0.0026(15) 0.0102(15) 0.0051(15) O2 0.079(2) 0.075(2) 0.0340(15) 0.0102(13) 0.0223(14) 0.0184(15) O3 0.0548(16) 0.075(2) 0.0531(17) -0.0286(15) 0.0151(13) -0.0060(15) C3 0.037(2) 0.049(2) 0.036(2) -0.0046(16) 0.0073(15) -0.0009(17) N3 0.0383(16) 0.0560(19) 0.0334(16) 0.0002(14) 0.0072(13) 0.0042(14) O4 0.073(2) 0.099(2) 0.0353(16) -0.0031(16) 0.0129(14) -0.0089(17) C4 0.039(2) 0.049(2) 0.035(2) 0.0014(16) 0.0067(15) 0.0002(17) N4 0.0463(19) 0.052(2) 0.0329(18) 0.0006(15) 0.0128(15) 0.0024(15) C5 0.0335(18) 0.038(2) 0.039(2) -0.0005(15) 0.0092(15) -0.0023(15) O5 0.0749(18) 0.0782(19) 0.0300(14) -0.0088(13) 0.0223(13) -0.0332(15) C6 0.0370(19) 0.047(2) 0.0339(19) -0.0039(16) 0.0073(15) -0.0003(16) C7 0.040(2) 0.041(2) 0.0413(19) -0.0036(16) 0.0101(15) 0.0024(16) C8 0.058(3) 0.097(3) 0.042(2) 0.011(2) -0.0038(19) -0.018(2) C9 0.059(3) 0.086(3) 0.036(2) 0.006(2) 0.0034(18) -0.014(2) C10 0.064(3) 0.083(3) 0.043(2) 0.014(2) 0.011(2) 0.018(2) C11 0.063(3) 0.083(3) 0.037(2) -0.007(2) 0.0048(19) 0.021(2) C12 0.044(2) 0.048(2) 0.0289(19) -0.0034(16) 0.0142(16) 0.0027(17) C13 0.043(2) 0.060(2) 0.034(2) -0.0023(18) 0.0049(16) -0.0025(18) C14 0.040(2) 0.064(3) 0.039(2) -0.0114(18) 0.0130(17) -0.0121(18) C15 0.054(2) 0.050(2) 0.033(2) -0.0084(16) 0.0198(17) -0.0110(18) C16 0.046(2) 0.078(3) 0.0260(19) 0.0054(18) 0.0027(16) 0.001(2) C17 0.037(2) 0.071(3) 0.041(2) -0.0026(19) 0.0162(17) 0.0010(18) C18 0.053(2) 0.062(3) 0.0270(19) -0.0037(17) 0.0180(16) -0.0120(19) C19 0.073(3) 0.046(2) 0.046(2) -0.0091(19) 0.020(2) -0.004(2) C20 0.069(3) 0.058(3) 0.033(2) 0.0072(19) 0.0125(18) 0.005(2) C21 0.042(2) 0.060(3) 0.033(2) -0.0058(18) 0.0157(16) -0.0020(18) C22 0.061(2) 0.051(2) 0.048(2) -0.0065(19) 0.0234(19) -0.0127(19) C23 0.068(3) 0.052(3) 0.034(2) 0.0045(18) 0.0186(18) -0.012(2) C24 0.066(3) 0.041(2) 0.045(2) 0.0013(18) 0.031(2) 0.0097(19) C25 0.037(2) 0.084(3) 0.041(2) -0.016(2) 0.0138(17) 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 Cd1 O2 2.282(3) 1_554 ? Cd1 N1 2.301(3) . ? Cd1 O4 2.350(3) . ? Cd1 N3 2.369(3) 1_655 ? Cd1 O3 2.474(3) . ? Cd1 O1 2.544(3) 3_567 ? Cd1 C25 2.743(4) . ? N1 C1 1.340(4) . ? N1 N2 1.350(4) . ? C1 C2 1.405(4) . ? C1 C8 1.489(5) . ? O1 C24 1.265(5) . ? O1 Cd1 2.544(3) 3_567 ? N2 C3 1.339(4) . ? N2 H222 0.77(4) . ? C2 C3 1.384(4) . ? C2 C7 1.512(4) . ? O2 C24 1.254(4) . ? O2 Cd1 2.282(3) 1_556 ? O3 C25 1.254(5) . ? C3 C9 1.490(4) . ? N3 C6 1.340(4) . ? N3 N4 1.354(4) . ? N3 Cd1 2.369(3) 1_455 ? O4 C25 1.249(5) . ? C4 N4 1.346(4) . ? C4 C5 1.375(4) . ? C4 C10 1.493(5) . ? N4 H444 0.85(3) . ? C5 C6 1.407(4) . ? C5 C7 1.510(4) . ? O5 C18 1.383(4) . ? O5 C15 1.390(4) . ? C6 C11 1.482(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.378(5) . ? C12 C13 1.386(5) . ? C12 C24 1.508(5) . ? C13 C14 1.385(5) . ? C13 H13A 0.9300 . ? C14 C15 1.371(5) . ? C14 H14A 0.9300 . ? C15 C16 1.379(5) . ? C16 C17 1.382(5) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 C23 1.369(5) . ? C18 C19 1.380(5) . ? C19 C20 1.392(5) . ? C19 H19A 0.9300 . ? C20 C21 1.382(5) . ? C20 H20A 0.9300 . ? C21 C22 1.377(5) . ? C21 C25 1.514(5) . ? C22 C23 1.386(5) . ? C22 H22A 0.9300 . ? C23 H23A 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 Cd1 N1 126.85(10) 1_554 . ? O2 Cd1 O4 90.30(10) 1_554 . ? N1 Cd1 O4 138.44(10) . . ? O2 Cd1 N3 82.99(9) 1_554 1_655 ? N1 Cd1 N3 95.82(10) . 1_655 ? O4 Cd1 N3 107.97(10) . 1_655 ? O2 Cd1 O3 130.48(10) 1_554 . ? N1 Cd1 O3 100.52(9) . . ? O4 Cd1 O3 54.19(10) . . ? N3 Cd1 O3 78.22(9) 1_655 . ? O2 Cd1 O1 96.03(9) 1_554 3_567 ? N1 Cd1 O1 82.39(9) . 3_567 ? O4 Cd1 O1 74.95(10) . 3_567 ? N3 Cd1 O1 176.90(9) 1_655 3_567 ? O3 Cd1 O1 104.56(8) . 3_567 ? O2 Cd1 C25 111.35(12) 1_554 . ? N1 Cd1 C25 121.74(11) . . ? O4 Cd1 C25 27.00(11) . . ? N3 Cd1 C25 93.22(11) 1_655 . ? O3 Cd1 C25 27.18(11) . . ? O1 Cd1 C25 89.88(11) 3_567 . ? C1 N1 N2 104.8(3) . . ? C1 N1 Cd1 137.6(2) . . ? N2 N1 Cd1 116.8(2) . . ? N1 C1 C2 111.0(3) . . ? N1 C1 C8 120.2(3) . . ? C2 C1 C8 128.8(3) . . ? C24 O1 Cd1 120.8(2) . 3_567 ? C3 N2 N1 112.6(3) . . ? C3 N2 H222 127(3) . . ? N1 N2 H222 120(3) . . ? C3 C2 C1 104.7(3) . . ? C3 C2 C7 127.7(3) . . ? C1 C2 C7 127.5(3) . . ? C24 O2 Cd1 102.5(2) . 1_556 ? C25 O3 Cd1 88.5(2) . . ? N2 C3 C2 106.9(3) . . ? N2 C3 C9 120.2(3) . . ? C2 C3 C9 132.9(3) . . ? C6 N3 N4 104.7(3) . . ? C6 N3 Cd1 134.0(2) . 1_455 ? N4 N3 Cd1 117.8(2) . 1_455 ? C25 O4 Cd1 94.3(3) . . ? N4 C4 C5 106.8(3) . . ? N4 C4 C10 120.2(3) . . ? C5 C4 C10 132.9(3) . . ? C4 N4 N3 112.5(3) . . ? C4 N4 H444 128(2) . . ? N3 N4 H444 119(2) . . ? C4 C5 C6 105.1(3) . . ? C4 C5 C7 127.6(3) . . ? C6 C5 C7 127.3(3) . . ? C18 O5 C15 119.6(3) . . ? N3 C6 C5 110.9(3) . . ? N3 C6 C11 120.0(3) . . ? C5 C6 C11 129.0(3) . . ? C5 C7 C2 117.2(3) . . ? C5 C7 H7A 108.0 . . ? C2 C7 H7A 108.0 . . ? C5 C7 H7B 108.0 . . ? C2 C7 H7B 108.0 . . ? H7A C7 H7B 107.2 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 119.5(3) . . ? C17 C12 C24 120.1(3) . . ? C13 C12 C24 120.4(3) . . ? C14 C13 C12 119.4(3) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 O5 117.0(3) . . ? C16 C15 O5 122.2(3) . . ? C15 C16 C17 118.8(3) . . ? C15 C16 H16A 120.6 . . ? C17 C16 H16A 120.6 . . ? C12 C17 C16 121.1(3) . . ? C12 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? C23 C18 C19 121.0(3) . . ? C23 C18 O5 121.9(3) . . ? C19 C18 O5 117.0(3) . . ? C18 C19 C20 118.6(4) . . ? C18 C19 H19A 120.7 . . ? C20 C19 H19A 120.7 . . ? C21 C20 C19 121.2(3) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C22 C21 C20 118.6(3) . . ? C22 C21 C25 120.0(4) . . ? C20 C21 C25 121.3(4) . . ? C21 C22 C23 120.9(4) . . ? C21 C22 H22A 119.5 . . ? C23 C22 H22A 119.5 . . ? C18 C23 C22 119.5(3) . . ? C18 C23 H23A 120.2 . . ? C22 C23 H23A 120.2 . . ? O2 C24 O1 123.1(3) . . ? O2 C24 C12 118.8(4) . . ? O1 C24 C12 118.2(4) . . ? O4 C25 O3 123.0(4) . . ? O4 C25 C21 119.1(4) . . ? O3 C25 C21 117.9(4) . . ? O4 C25 Cd1 58.7(2) . . ? O3 C25 Cd1 64.3(2) . . ? C21 C25 Cd1 177.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.87 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.363 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.064 # Attachment '- OBA_Co.cif' data_09ag002_0m _database_code_depnum_ccdc_archive 'CCDC 790292' #TrackingRef '- OBA_Co.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Co N4 O5' _chemical_formula_weight 519.41 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 Hexagonal _symmetry_space_group_name_H-M P6(1)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+5/6' '-x+y, y, -z+1/2' 'x, x-y, -z+1/6' _cell_length_a 9.6221(2) _cell_length_b 9.6221(2) _cell_length_c 48.4414(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3884.07(15) _cell_formula_units_Z 6 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7327 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.31 _exptl_crystal_description Block _exptl_crystal_colour Purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1614 _exptl_absorpt_coefficient_mu 0.703 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.832350 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0615 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 50807 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_limit_l_max 62 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2864 _reflns_number_gt 2561 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0381P)^2^+1.7728P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 2864 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.011 _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 0.70238(3) 0.29762(3) 0.9167 0.03076(13) Uani 1 2 d S . . O1 O 0.7163(2) 0.44619(19) 0.94475(4) 0.0385(4) Uani 1 1 d . . . N1 N 0.5966(2) 0.0689(2) 0.92869(4) 0.0313(4) Uani 1 1 d . . . C1 C 0.5788(3) -0.0649(3) 0.91664(5) 0.0300(5) Uani 1 1 d . . . O2 O 0.4780(2) 0.2978(2) 0.96508(4) 0.0417(4) Uani 1 1 d . . . C2 C 0.4385(3) -0.1991(3) 0.92623(5) 0.0295(5) Uani 1 1 d . . . N2 N 0.4670(2) 0.0193(2) 0.94570(4) 0.0324(5) Uani 1 1 d . . . H222 H 0.456(3) 0.097(3) 0.9538(5) 0.031(7) Uiso 1 1 d . . . O3 O 0.6446(3) 1.0000 1.0000 0.0397(6) Uani 1 2 d S . . C3 C 0.3713(3) -0.1407(3) 0.94464(5) 0.0331(5) Uani 1 1 d . . . C7 C 0.3700(2) -0.3700(2) 0.9167 0.0343(7) Uani 1 2 d S . . H7A H 0.3737 -0.4346 0.9317 0.051 Uiso 0.50 1 calc PR . . H7B H 0.4346 -0.3737 0.9016 0.051 Uiso 0.50 1 calc PR . . C8 C 0.6976(3) -0.0571(3) 0.89606(5) 0.0401(6) Uani 1 1 d . . . H8A H 0.7727 0.0531 0.8918 0.060 Uiso 1 1 calc R . . H8B H 0.6427 -0.1120 0.8795 0.060 Uiso 1 1 calc R . . H8C H 0.7540 -0.1072 0.9036 0.060 Uiso 1 1 calc R . . C9 C 0.2199(3) -0.2229(3) 0.96144(6) 0.0449(7) Uani 1 1 d . . . H9A H 0.2195 -0.1488 0.9747 0.067 Uiso 1 1 calc R . . H9B H 0.2148 -0.3129 0.9709 0.067 Uiso 1 1 calc R . . H9C H 0.1287 -0.2596 0.9495 0.067 Uiso 1 1 calc R . . C12 C 0.6193(3) 0.5806(3) 0.97222(5) 0.0310(5) Uani 1 1 d . . . C13 C 0.7539(3) 0.7271(3) 0.96603(5) 0.0365(6) Uani 1 1 d . . . H13A H 0.8348 0.7296 0.9552 0.044 Uiso 1 1 calc R . . C14 C 0.7694(3) 0.8697(3) 0.97580(5) 0.0378(6) Uani 1 1 d . . . H14A H 0.8598 0.9676 0.9716 0.045 Uiso 1 1 calc R . . C15 C 0.6475(3) 0.8634(3) 0.99191(5) 0.0329(5) Uani 1 1 d . . . C16 C 0.5141(3) 0.7185(3) 0.99868(5) 0.0365(6) Uani 1 1 d . . . H16A H 0.4341 0.7162 1.0097 0.044 Uiso 1 1 calc R . . C17 C 0.5001(3) 0.5773(3) 0.98897(5) 0.0362(6) Uani 1 1 d . . . H17A H 0.4108 0.4797 0.9936 0.043 Uiso 1 1 calc R . . C18 C 0.5992(3) 0.4284(3) 0.96012(5) 0.0343(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02374(16) 0.02374(16) 0.0364(2) 0.00129(17) 0.00129(17) 0.00556(18) O1 0.0375(10) 0.0309(9) 0.0445(10) -0.0035(7) 0.0027(8) 0.0152(8) N1 0.0229(10) 0.0246(10) 0.0362(11) 0.0002(8) -0.0004(9) 0.0043(8) C1 0.0233(11) 0.0270(11) 0.0337(12) 0.0005(10) -0.0028(10) 0.0081(9) O2 0.0378(10) 0.0312(10) 0.0509(11) -0.0045(9) 0.0018(8) 0.0135(9) C2 0.0223(11) 0.0265(12) 0.0314(12) -0.0005(9) -0.0038(9) 0.0059(9) N2 0.0272(10) 0.0283(10) 0.0316(11) -0.0027(9) 0.0024(9) 0.0064(9) O3 0.0319(10) 0.0330(13) 0.0545(17) -0.0059(12) -0.0029(6) 0.0165(7) C3 0.0264(12) 0.0271(12) 0.0322(12) 0.0011(10) -0.0021(11) 0.0032(10) C7 0.0257(11) 0.0257(11) 0.0424(19) -0.0024(13) -0.0024(13) 0.0062(13) C8 0.0331(13) 0.0316(13) 0.0472(16) 0.0024(12) 0.0078(12) 0.0098(11) C9 0.0359(15) 0.0355(14) 0.0447(15) 0.0007(13) 0.0105(13) 0.0039(11) C12 0.0312(12) 0.0292(12) 0.0310(13) -0.0006(10) -0.0031(10) 0.0139(10) C13 0.0339(13) 0.0341(14) 0.0418(14) 0.0001(11) 0.0045(11) 0.0171(11) C14 0.0304(12) 0.0280(13) 0.0477(15) -0.0008(12) 0.0038(11) 0.0092(11) C15 0.0341(13) 0.0318(13) 0.0347(13) -0.0019(11) -0.0051(10) 0.0180(11) C16 0.0318(13) 0.0377(14) 0.0375(13) -0.0007(11) 0.0027(11) 0.0155(11) C17 0.0320(13) 0.0310(13) 0.0393(14) 0.0026(11) -0.0008(11) 0.0111(11) C18 0.0369(15) 0.0314(14) 0.0345(13) -0.0014(10) -0.0076(11) 0.0172(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 1.9288(17) . ? Co1 O1 1.9288(17) 10_666 ? Co1 N1 1.9946(19) . ? Co1 N1 1.9946(19) 10_666 ? O1 C18 1.289(3) . ? N1 C1 1.345(3) . ? N1 N2 1.366(3) . ? C1 C2 1.401(3) . ? C1 C8 1.490(3) . ? O2 C18 1.238(3) . ? C2 C3 1.375(3) . ? C2 C7 1.506(3) . ? N2 C3 1.344(3) . ? N2 H222 0.90(3) . ? O3 C15 1.385(3) 8_677 ? O3 C15 1.385(3) . ? C3 C9 1.502(3) . ? C7 C2 1.506(3) 10_556 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 C13 1.388(4) . ? C12 C17 1.393(3) . ? C12 C18 1.497(3) . ? C13 C14 1.388(4) . ? C13 H13A 0.9300 . ? C14 C15 1.385(3) . ? C14 H14A 0.9300 . ? C15 C16 1.381(4) . ? C16 C17 1.379(4) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 108.87(11) . 10_666 ? O1 Co1 N1 114.82(8) . . ? O1 Co1 N1 100.23(8) 10_666 . ? O1 Co1 N1 100.23(8) . 10_666 ? O1 Co1 N1 114.82(8) 10_666 10_666 ? N1 Co1 N1 118.20(13) . 10_666 ? C18 O1 Co1 125.23(16) . . ? C1 N1 N2 105.70(19) . . ? C1 N1 Co1 132.85(17) . . ? N2 N1 Co1 115.76(15) . . ? N1 C1 C2 109.9(2) . . ? N1 C1 C8 121.0(2) . . ? C2 C1 C8 129.1(2) . . ? C3 C2 C1 105.8(2) . . ? C3 C2 C7 127.3(2) . . ? C1 C2 C7 126.7(2) . . ? C3 N2 N1 111.1(2) . . ? C3 N2 H222 132.5(17) . . ? N1 N2 H222 116.0(17) . . ? C15 O3 C15 120.7(3) 8_677 . ? N2 C3 C2 107.4(2) . . ? N2 C3 C9 120.8(2) . . ? C2 C3 C9 131.8(2) . . ? C2 C7 C2 111.0(3) . 10_556 ? C2 C7 H7A 109.4 . . ? C2 C7 H7A 109.4 10_556 . ? C2 C7 H7B 109.4 . . ? C2 C7 H7B 109.4 10_556 . ? H7A C7 H7B 108.0 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C13 C12 C17 119.2(2) . . ? C13 C12 C18 120.5(2) . . ? C17 C12 C18 120.2(2) . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C15 C14 C13 118.6(2) . . ? C15 C14 H14A 120.7 . . ? C13 C14 H14A 120.7 . . ? C16 C15 C14 121.1(2) . . ? C16 C15 O3 116.2(2) . . ? C14 C15 O3 122.4(2) . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C12 120.2(2) . . ? C16 C17 H17A 119.9 . . ? C12 C17 H17A 119.9 . . ? O2 C18 O1 124.4(2) . . ? O2 C18 C12 120.9(2) . . ? O1 C18 C12 114.8(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.283 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.041 # Attachment '- OBA_Cu.cif' data_10ag007_0m _database_code_depnum_ccdc_archive 'CCDC 790293' #TrackingRef '- OBA_Cu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H67 Cu2 N9 O15' _chemical_formula_weight 1209.25 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 12.8829(5) _cell_length_b 14.1565(6) _cell_length_c 18.6819(7) _cell_angle_alpha 104.822(2) _cell_angle_beta 98.409(2) _cell_angle_gamma 113.3670(10) _cell_volume 2903.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1452 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.12 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.805 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790354 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0639 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 38600 _diffrn_reflns_av_R_equivalents 0.1247 _diffrn_reflns_av_sigmaI/netI 0.1094 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 24.51 _reflns_number_total 9655 _reflns_number_gt 5945 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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. Four restraintS, DFIX command, were used in order to refine hydrogen atoms of disordered solvent molecules. ; _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^)+(0.0529P)^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 9655 _refine_ls_number_parameters 731 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.05740(5) 0.11010(4) 0.03205(3) 0.01922(17) Uani 1 1 d . . . O1 O -0.4571(3) 0.3578(3) 0.45245(18) 0.0290(8) Uani 1 1 d . . . N1 N 0.1482(3) 0.2869(3) 0.0733(2) 0.0227(9) Uani 1 1 d . . . C1 C 0.1422(4) 0.3632(4) 0.1296(3) 0.0224(11) Uani 1 1 d . . . O1SA O 0.9754(3) 0.6258(3) 0.1255(2) 0.0434(10) Uani 1 1 d . . . N1SA N 1.1068(4) 0.6961(4) 0.0612(3) 0.0439(13) Uani 1 1 d . . . C1SA C 1.1315(6) 0.6905(6) -0.0132(4) 0.075(2) Uani 1 1 d . . . H1SG H 1.0668 0.6260 -0.0538 0.113 Uiso 1 1 calc R . . H1SH H 1.2050 0.6848 -0.0119 0.113 Uiso 1 1 calc R . . H1SI H 1.1391 0.7568 -0.0238 0.113 Uiso 1 1 calc R . . O1SB O 0.3154(3) 0.2864(3) -0.0880(2) 0.0426(10) Uani 1 1 d . . . N1SB N 0.2956(4) 0.1487(4) -0.1924(2) 0.0340(11) Uani 1 1 d . . . C1SB C 0.4002(6) 0.2130(5) -0.2108(4) 0.0606(19) Uani 1 1 d . . . H1SD H 0.4285 0.2909 -0.1819 0.091 Uiso 1 1 calc R . . H1SE H 0.3817 0.2005 -0.2662 0.091 Uiso 1 1 calc R . . H1SF H 0.4614 0.1911 -0.1968 0.091 Uiso 1 1 calc R . . O1S O 0.8038(5) 0.3573(4) 0.1853(3) 0.0900(18) Uani 1 1 d . A 1 N1S N 0.7323(7) 0.4803(5) 0.2151(5) 0.119(3) Uani 1 1 d . A 1 C1S C 0.7281(7) 0.5777(5) 0.2088(5) 0.084(3) Uani 1 1 d . A 1 H1SC H 0.7849 0.6105 0.1819 0.127 Uiso 1 1 calc R A 1 H1SB H 0.7479 0.6303 0.2605 0.127 Uiso 1 1 calc R A 1 H1SA H 0.6487 0.5590 0.1797 0.127 Uiso 1 1 calc R A 1 O1SC O 0.7805(6) 0.2872(6) 0.4816(4) 0.0349(18) Uiso 0.50 1 d P B 2 N1SC N 0.8469(10) 0.3325(8) 0.3820(6) 0.041(3) Uiso 0.50 1 d P B 2 C1SC C 0.9042(15) 0.3105(14) 0.3271(10) 0.091(5) Uiso 0.50 1 d P B 2 H1SL H 0.8994 0.2375 0.3188 0.137 Uiso 0.50 1 calc PR B 2 H1SK H 0.9870 0.3656 0.3454 0.137 Uiso 0.50 1 calc PR B 2 H1SJ H 0.8666 0.3130 0.2786 0.137 Uiso 0.50 1 calc PR B 2 O1SE O -0.6789(9) -0.0590(9) 0.5936(6) 0.042(3) Uiso 0.40 1 d P C 2 N1SE N -0.6050(13) 0.0467(12) 0.5086(9) 0.067(4) Uiso 0.40 1 d P C 2 C1SE C -0.5152(18) 0.1598(16) 0.5392(13) 0.068(6) Uiso 0.40 1 d P C 2 H1SP H -0.4753 0.1779 0.5932 0.103 Uiso 0.40 1 calc PR C 2 H1SQ H -0.5518 0.2080 0.5359 0.103 Uiso 0.40 1 calc PR C 2 H1SR H -0.4577 0.1701 0.5092 0.103 Uiso 0.40 1 calc PR C 2 O1SF O -0.6647(9) -0.0037(10) 0.6138(7) 0.100(4) Uiso 0.60 1 d P D 3 N1SF N -0.5538(6) 0.0855(6) 0.5633(4) 0.0272(17) Uiso 0.60 1 d P D 3 C1SF C -0.4521(9) 0.1180(8) 0.6232(6) 0.051(3) Uiso 0.60 1 d P D 3 H1SU H -0.4741 0.0790 0.6592 0.077 Uiso 0.60 1 calc PR D 3 H1ST H -0.4171 0.1972 0.6507 0.077 Uiso 0.60 1 calc PR D 3 H1SS H -0.3948 0.1003 0.6011 0.077 Uiso 0.60 1 calc PR D 3 O1SD O 0.8698(7) 0.4260(7) 0.5010(5) 0.052(2) Uiso 0.50 1 d P E 3 N1SD N 0.8976(10) 0.3399(8) 0.3925(6) 0.033(3) Uiso 0.50 1 d P E 3 C1SD C 0.9877(10) 0.4358(9) 0.3843(7) 0.043(3) Uiso 0.50 1 d P E 3 H1SO H 0.9907 0.5024 0.4188 0.065 Uiso 0.50 1 calc PR E 3 H1SN H 0.9687 0.4331 0.3309 0.065 Uiso 0.50 1 calc PR E 3 H1SM H 1.0644 0.4363 0.3978 0.065 Uiso 0.50 1 calc PR E 3 O1A O 0.4129(3) 0.3854(3) -0.44596(19) 0.0297(8) Uani 1 1 d . . . Cu2 Cu -0.42987(5) 0.47693(5) 0.54555(3) 0.02202(17) Uani 1 1 d . . . N2 N 0.2176(3) 0.3426(3) 0.0352(2) 0.0249(10) Uani 1 1 d . . . H2A H 0.2351 0.3112 -0.0052 0.030 Uiso 1 1 calc R . . C2 C 0.2085(4) 0.4676(4) 0.1268(3) 0.0218(11) Uani 1 1 d . . . C2SA C 1.1912(5) 0.7879(5) 0.1279(4) 0.059(2) Uani 1 1 d . . . H2SD H 1.1661 0.7809 0.1741 0.089 Uiso 1 1 calc R . . H2SE H 1.1963 0.8562 0.1217 0.089 Uiso 1 1 calc R . . H2SF H 1.2686 0.7891 0.1332 0.089 Uiso 1 1 calc R . . C2SB C 0.2324(5) 0.0316(4) -0.2375(3) 0.0399(15) Uani 1 1 d . . . H2SG H 0.1574 -0.0008 -0.2253 0.060 Uiso 1 1 calc R . . H2SH H 0.2802 -0.0043 -0.2249 0.060 Uiso 1 1 calc R . . H2SI H 0.2171 0.0214 -0.2926 0.060 Uiso 1 1 calc R . . C2S C 0.6570(13) 0.4252(9) 0.2563(10) 0.370(17) Uani 1 1 d . A 1 H2SC H 0.6694 0.3623 0.2595 0.555 Uiso 1 1 calc RD A 1 H2SB H 0.5746 0.3997 0.2290 0.555 Uiso 1 1 calc R A 1 H2SA H 0.6756 0.4761 0.3084 0.555 Uiso 1 1 calc RD A 1 C2SC C 0.8307(12) 0.4288(11) 0.4016(8) 0.072(4) Uiso 0.50 1 d P B 2 H2SL H 0.7497 0.4092 0.4040 0.109 Uiso 0.50 1 calc PRD B 2 H2SK H 0.8458 0.4631 0.3623 0.109 Uiso 0.50 1 calc PRD B 2 H2SJ H 0.8855 0.4804 0.4519 0.109 Uiso 0.50 1 calc PR B 2 C2SE C -0.6361(18) -0.0031(16) 0.4210(11) 0.086(6) Uiso 0.40 1 d P C 2 H2SP H -0.6965 -0.0796 0.4036 0.129 Uiso 0.40 1 calc PR C 2 H2SQ H -0.5656 -0.0004 0.4058 0.129 Uiso 0.40 1 calc PR C 2 H2SR H -0.6662 0.0385 0.3972 0.129 Uiso 0.40 1 calc PR C 2 C2SF C -0.5440(11) 0.1388(10) 0.5037(7) 0.052(3) Uiso 0.60 1 d P D 3 H2SU H -0.6198 0.1032 0.4643 0.078 Uiso 0.60 1 calc PR D 3 H2ST H -0.4835 0.1316 0.4796 0.078 Uiso 0.60 1 calc PR D 3 H2SS H -0.5221 0.2166 0.5280 0.078 Uiso 0.60 1 calc PR D 3 C2SD C 0.8585(11) 0.2353(9) 0.3318(7) 0.042(3) Uiso 0.50 1 d P E 3 H2SO H 0.7973 0.1773 0.3429 0.062 Uiso 0.50 1 calc PR E 3 H2SN H 0.9253 0.2190 0.3293 0.062 Uiso 0.50 1 calc PR E 3 H2SM H 0.8266 0.2391 0.2823 0.062 Uiso 0.50 1 calc PR E 3 O2A O 0.2936(3) 0.4249(3) -0.52013(19) 0.0292(8) Uani 1 1 d . . . O2 O -0.5804(3) 0.3924(3) 0.37783(18) 0.0294(8) Uani 1 1 d . . . O3 O -0.0984(3) 0.0905(3) 0.04404(19) 0.0270(8) Uani 1 1 d . . . O3A O 0.0073(3) 0.0964(3) -0.07659(18) 0.0265(8) Uani 1 1 d . . . C3 C 0.2562(4) 0.4513(4) 0.0663(3) 0.0228(11) Uani 1 1 d . . . C3SA C 1.0072(5) 0.6267(5) 0.0663(4) 0.0366(14) Uani 1 1 d . . . H3SA H 0.9534 0.5711 0.0195 0.042(17) Uiso 1 1 calc R . . C3SB C 0.2631(5) 0.1895(5) -0.1313(3) 0.0379(14) Uani 1 1 d . . . H3SB H 0.1961 0.1412 -0.1208 0.427 Uiso 1 1 calc R . . C3S C 0.7973(6) 0.4411(5) 0.1829(4) 0.0591(19) Uani 1 1 d . A 1 H3S H 0.8432 0.4806 0.1552 0.09(2) Uiso 1 1 calc R A 1 C3SC C 0.8200(11) 0.2714(11) 0.4274(7) 0.052(3) Uiso 0.50 1 d P B 2 H3SC H 0.8337 0.2087 0.4154 0.062 Uiso 0.50 1 calc PR B 2 C3SE C -0.6632(12) -0.0174(12) 0.5420(8) 0.019(3) Uiso 0.40 1 d P C 2 H3SE H -0.7393 -0.0561 0.5063 0.022 Uiso 0.40 1 calc PR C 2 C3SF C -0.6599(12) 0.0167(10) 0.5635(8) 0.052(4) Uiso 0.60 1 d P D 3 H3SF H -0.7272 -0.0123 0.5209 0.062 Uiso 0.60 1 calc PR D 3 C3SD C 0.8440(10) 0.3499(10) 0.4500(7) 0.036(3) Uiso 0.50 1 d P E 3 H3SD H 0.7775 0.2857 0.4466 0.043 Uiso 0.50 1 calc PR E 3 N3 N 0.3416(4) 0.5692(3) 0.3737(2) 0.0266(10) Uani 1 1 d . . . O4 O -0.1956(3) -0.0933(3) -0.01066(18) 0.0236(8) Uani 1 1 d . . . O4A O -0.0896(3) -0.0879(3) -0.13162(17) 0.0249(8) Uani 1 1 d . . . C4 C 0.3438(4) 0.5614(4) 0.3015(3) 0.0210(11) Uani 1 1 d . . . N4 N 0.2557(4) 0.5995(4) 0.3839(2) 0.0390(12) Uani 1 1 d . . . H4A H 0.2354 0.6106 0.4271 0.047 Uiso 1 1 calc R . . O5 O -0.5792(3) -0.0051(3) 0.12923(19) 0.0301(9) Uani 1 1 d . . . O5A O -0.0783(3) 0.0571(3) -0.42677(19) 0.0381(10) Uani 1 1 d . . . C5 C 0.2585(4) 0.5856(4) 0.2654(3) 0.0242(12) Uani 1 1 d . . . C6 C 0.2050(5) 0.6109(4) 0.3202(3) 0.0359(14) Uani 1 1 d . . . C7 C 0.2273(5) 0.5759(4) 0.1824(3) 0.0264(12) Uani 1 1 d . . . H7A H 0.2912 0.6365 0.1743 0.040 Uiso 1 1 calc R . . H7B H 0.1546 0.5841 0.1706 0.040 Uiso 1 1 calc R . . C8 C 0.0725(5) 0.3299(4) 0.1841(3) 0.0301(13) Uani 1 1 d . . . H8A H 0.0290 0.2498 0.1664 0.045 Uiso 1 1 calc R . . H8B H 0.0168 0.3611 0.1857 0.045 Uiso 1 1 calc R . . H8C H 0.1259 0.3571 0.2358 0.045 Uiso 1 1 calc R . . C9 C 0.3341(5) 0.5295(4) 0.0334(3) 0.0358(14) Uani 1 1 d . . . H9A H 0.4018 0.5154 0.0287 0.054 Uiso 1 1 calc R . . H9B H 0.3618 0.6050 0.0677 0.054 Uiso 1 1 calc R . . H9C H 0.2894 0.5191 -0.0175 0.054 Uiso 1 1 calc R . . C10 C 0.4284(4) 0.5303(4) 0.2675(3) 0.0312(13) Uani 1 1 d . . . H10A H 0.4961 0.5471 0.3089 0.047 Uiso 1 1 calc R . . H10B H 0.4554 0.5717 0.2335 0.047 Uiso 1 1 calc R . . H10C H 0.3894 0.4516 0.2377 0.047 Uiso 1 1 calc R . . C11 C 0.1107(6) 0.6470(6) 0.3189(3) 0.067(2) Uani 1 1 d . . . H11A H 0.0624 0.6184 0.3515 0.100 Uiso 1 1 calc R . . H11B H 0.0610 0.6191 0.2659 0.100 Uiso 1 1 calc R . . H11C H 0.1467 0.7273 0.3384 0.100 Uiso 1 1 calc R . . C12 C -0.5422(4) 0.2450(4) 0.3210(3) 0.0203(11) Uani 1 1 d . . . C12A C 0.2100(4) 0.2925(4) -0.4618(3) 0.0238(12) Uani 1 1 d . . . C13 C -0.4805(4) 0.1853(4) 0.3283(3) 0.0237(12) Uani 1 1 d . . . H13B H -0.4303 0.2017 0.3771 0.028 Uiso 1 1 calc R . . C13A C 0.2252(5) 0.2257(4) -0.4226(3) 0.0330(13) Uani 1 1 d . . . H14A H 0.3021 0.2339 -0.4041 0.040 Uiso 1 1 calc R . . C14 C -0.4917(4) 0.1018(4) 0.2647(3) 0.0267(12) Uani 1 1 d . . . H14B H -0.4496 0.0608 0.2698 0.032 Uiso 1 1 calc R . . C14A C 0.1314(5) 0.1479(5) -0.4101(3) 0.0382(14) Uani 1 1 d . . . H14C H 0.1430 0.1024 -0.3835 0.046 Uiso 1 1 calc R . . C15 C -0.5644(4) 0.0789(4) 0.1943(3) 0.0240(12) Uani 1 1 d . . . C15A C 0.0204(5) 0.1369(4) -0.4365(3) 0.0309(13) Uani 1 1 d . . . C16 C -0.6278(4) 0.1376(4) 0.1862(3) 0.0287(12) Uani 1 1 d . . . H16B H -0.6780 0.1213 0.1374 0.034 Uiso 1 1 calc R . . C16A C 0.0020(5) 0.2007(4) -0.4759(3) 0.0360(14) Uani 1 1 d . . . H16A H -0.0752 0.1921 -0.4939 0.043 Uiso 1 1 calc R . . C17 C -0.6166(4) 0.2199(4) 0.2501(3) 0.0255(12) Uani 1 1 d . . . H17B H -0.6602 0.2596 0.2453 0.031 Uiso 1 1 calc R . . C17A C 0.0969(5) 0.2779(4) -0.4893(3) 0.0361(14) Uani 1 1 d . . . H17A H 0.0842 0.3213 -0.5175 0.043 Uiso 1 1 calc R . . C18 C -0.2919(4) 0.0006(4) 0.0505(3) 0.0237(12) Uani 1 1 d . . . C18A C -0.0597(4) 0.0200(4) -0.2120(3) 0.0249(12) Uani 1 1 d . . . C19 C -0.2861(4) 0.0976(4) 0.0979(3) 0.0207(11) Uani 1 1 d . . . H19B H -0.2161 0.1643 0.1117 0.025 Uiso 1 1 calc R . . C19A C -0.1123(4) -0.0713(4) -0.2796(3) 0.0289(12) Uani 1 1 d . . . H19A H -0.1455 -0.1429 -0.2768 0.035 Uiso 1 1 calc R . . C20 C -0.3794(4) 0.0985(4) 0.1250(3) 0.0243(12) Uani 1 1 d . . . H20B H -0.3739 0.1652 0.1571 0.029 Uiso 1 1 calc R . . C20A C -0.1165(4) -0.0580(4) -0.3508(3) 0.0303(13) Uani 1 1 d . . . H20A H -0.1519 -0.1202 -0.3969 0.036 Uiso 1 1 calc R . . C21 C -0.4814(4) 0.0015(4) 0.1053(3) 0.0240(12) Uani 1 1 d . . . C21A C -0.0684(5) 0.0466(4) -0.3538(3) 0.0303(13) Uani 1 1 d . . . C22 C -0.4911(4) -0.0962(4) 0.0565(3) 0.0247(12) Uani 1 1 d . . . H22B H -0.5619 -0.1623 0.0422 0.030 Uiso 1 1 calc R . . C22A C -0.0179(4) 0.1383(4) -0.2877(3) 0.0304(13) Uani 1 1 d . . . H22A H 0.0133 0.2098 -0.2907 0.037 Uiso 1 1 calc R . . C23 C -0.3972(4) -0.0964(4) 0.0293(3) 0.0257(12) Uani 1 1 d . . . H23B H -0.4039 -0.1628 -0.0042 0.031 Uiso 1 1 calc R . . C23A C -0.0139(4) 0.1239(4) -0.2176(3) 0.0288(12) Uani 1 1 d . . . H23A H 0.0211 0.1864 -0.1718 0.035 Uiso 1 1 calc R . . C24 C -0.5248(4) 0.3383(4) 0.3891(3) 0.0222(11) Uani 1 1 d . . . C24A C 0.3132(4) 0.3748(4) -0.4771(3) 0.0235(12) Uani 1 1 d . . . C25A C -0.0474(4) 0.0080(4) -0.1344(3) 0.0228(11) Uani 1 1 d . . . C25 C -0.1875(4) -0.0006(4) 0.0260(3) 0.0221(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0181(3) 0.0197(3) 0.0188(3) 0.0064(3) 0.0078(3) 0.0068(3) O1 0.032(2) 0.033(2) 0.021(2) 0.0067(17) 0.0020(17) 0.0176(18) N1 0.022(2) 0.022(2) 0.020(2) 0.0058(19) 0.0091(19) 0.0053(19) C1 0.021(3) 0.026(3) 0.013(3) 0.000(2) 0.002(2) 0.008(2) O1SA 0.042(3) 0.042(2) 0.049(3) 0.021(2) 0.019(2) 0.017(2) N1SA 0.035(3) 0.049(3) 0.066(4) 0.038(3) 0.023(3) 0.023(3) C1SA 0.074(5) 0.127(7) 0.093(6) 0.086(6) 0.060(5) 0.069(5) O1SB 0.048(3) 0.040(2) 0.038(2) 0.010(2) 0.021(2) 0.017(2) N1SB 0.037(3) 0.040(3) 0.029(3) 0.014(2) 0.014(2) 0.019(2) C1SB 0.066(5) 0.054(4) 0.058(5) 0.021(4) 0.039(4) 0.016(4) O1S 0.108(4) 0.050(3) 0.150(5) 0.047(3) 0.088(4) 0.047(3) N1S 0.142(7) 0.045(4) 0.237(9) 0.073(5) 0.165(7) 0.055(4) C1S 0.082(6) 0.042(4) 0.142(8) 0.031(5) 0.065(6) 0.029(4) O1A 0.025(2) 0.037(2) 0.026(2) 0.0155(17) 0.0075(17) 0.0093(18) Cu2 0.0238(4) 0.0249(4) 0.0180(4) 0.0082(3) 0.0066(3) 0.0111(3) N2 0.024(2) 0.027(2) 0.020(2) 0.007(2) 0.012(2) 0.007(2) C2 0.021(3) 0.022(3) 0.017(3) 0.005(2) -0.003(2) 0.007(2) C2SA 0.040(4) 0.037(4) 0.114(6) 0.036(4) 0.039(4) 0.017(3) C2SB 0.054(4) 0.039(4) 0.032(3) 0.015(3) 0.014(3) 0.023(3) C2S 0.48(3) 0.169(12) 0.81(4) 0.32(2) 0.60(3) 0.241(16) O2A 0.025(2) 0.036(2) 0.035(2) 0.0227(18) 0.0140(17) 0.0130(17) O2 0.039(2) 0.032(2) 0.021(2) 0.0079(17) 0.0076(17) 0.0202(18) O3 0.020(2) 0.026(2) 0.034(2) 0.0091(17) 0.0137(17) 0.0096(17) O3A 0.029(2) 0.025(2) 0.022(2) 0.0077(17) 0.0061(16) 0.0088(17) C3 0.024(3) 0.019(3) 0.018(3) 0.005(2) 0.003(2) 0.004(2) C3SA 0.032(4) 0.046(4) 0.036(4) 0.022(3) 0.010(3) 0.017(3) C3SB 0.039(4) 0.050(4) 0.037(4) 0.021(3) 0.015(3) 0.026(3) C3S 0.059(5) 0.045(4) 0.081(5) 0.025(4) 0.047(4) 0.020(4) N3 0.034(3) 0.035(3) 0.015(2) 0.005(2) 0.005(2) 0.023(2) O4 0.0217(19) 0.0246(19) 0.0224(19) 0.0031(16) 0.0094(16) 0.0105(16) O4A 0.027(2) 0.026(2) 0.0186(19) 0.0084(16) 0.0069(15) 0.0074(16) C4 0.027(3) 0.020(3) 0.015(3) 0.006(2) 0.004(2) 0.011(2) N4 0.043(3) 0.071(3) 0.018(3) 0.012(2) 0.012(2) 0.042(3) O5 0.0194(19) 0.033(2) 0.026(2) -0.0029(17) 0.0117(17) 0.0072(17) O5A 0.028(2) 0.048(2) 0.025(2) 0.0202(19) 0.0037(17) 0.0015(19) C5 0.033(3) 0.016(3) 0.020(3) 0.003(2) -0.001(2) 0.012(2) C6 0.040(4) 0.048(4) 0.024(3) 0.003(3) 0.001(3) 0.032(3) C7 0.032(3) 0.022(3) 0.022(3) 0.005(2) 0.002(2) 0.012(2) C8 0.035(3) 0.022(3) 0.025(3) 0.005(2) 0.011(3) 0.006(3) C9 0.046(4) 0.028(3) 0.027(3) 0.013(3) 0.016(3) 0.007(3) C10 0.031(3) 0.046(3) 0.025(3) 0.016(3) 0.011(3) 0.021(3) C11 0.072(5) 0.118(6) 0.041(4) 0.017(4) 0.011(4) 0.080(5) C12 0.021(3) 0.024(3) 0.017(3) 0.008(2) 0.010(2) 0.010(2) C12A 0.024(3) 0.027(3) 0.017(3) 0.005(2) 0.007(2) 0.009(2) C13 0.017(3) 0.032(3) 0.022(3) 0.011(2) 0.009(2) 0.009(2) C13A 0.029(3) 0.044(3) 0.026(3) 0.020(3) 0.005(3) 0.013(3) C14 0.021(3) 0.029(3) 0.028(3) 0.007(3) 0.012(3) 0.010(2) C14A 0.033(4) 0.053(4) 0.035(3) 0.031(3) 0.008(3) 0.017(3) C15 0.015(3) 0.027(3) 0.023(3) 0.006(2) 0.013(2) 0.003(2) C15A 0.027(3) 0.037(3) 0.020(3) 0.012(3) 0.010(2) 0.004(3) C16 0.022(3) 0.037(3) 0.026(3) 0.012(3) 0.008(2) 0.011(3) C16A 0.023(3) 0.052(4) 0.043(4) 0.030(3) 0.015(3) 0.016(3) C17 0.022(3) 0.034(3) 0.020(3) 0.007(2) 0.006(2) 0.013(2) C17A 0.040(4) 0.042(3) 0.034(3) 0.020(3) 0.012(3) 0.021(3) C18 0.027(3) 0.029(3) 0.018(3) 0.011(2) 0.008(2) 0.013(3) C18A 0.025(3) 0.027(3) 0.025(3) 0.010(2) 0.010(2) 0.012(2) C19 0.020(3) 0.022(3) 0.018(3) 0.008(2) 0.008(2) 0.006(2) C19A 0.026(3) 0.033(3) 0.029(3) 0.016(3) 0.010(3) 0.010(3) C20 0.023(3) 0.026(3) 0.025(3) 0.009(2) 0.007(2) 0.012(2) C20A 0.032(3) 0.031(3) 0.019(3) 0.006(2) 0.011(2) 0.006(3) C21 0.022(3) 0.032(3) 0.018(3) 0.006(2) 0.010(2) 0.012(3) C21A 0.028(3) 0.040(3) 0.022(3) 0.015(3) 0.008(3) 0.012(3) C22 0.016(3) 0.028(3) 0.020(3) 0.002(2) 0.005(2) 0.003(2) C22A 0.031(3) 0.032(3) 0.032(3) 0.018(3) 0.012(3) 0.013(3) C23 0.024(3) 0.023(3) 0.025(3) 0.001(2) 0.006(2) 0.010(2) C23A 0.031(3) 0.028(3) 0.025(3) 0.004(2) 0.009(3) 0.014(3) C24 0.020(3) 0.026(3) 0.017(3) 0.009(2) 0.008(2) 0.004(2) C24A 0.026(3) 0.023(3) 0.016(3) -0.003(2) 0.009(2) 0.011(2) C25A 0.015(3) 0.029(3) 0.028(3) 0.011(3) 0.011(2) 0.010(2) C25 0.015(3) 0.031(3) 0.017(3) 0.012(2) 0.004(2) 0.005(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 Cu1 O3 1.969(3) . ? Cu1 O4 1.970(3) 2 ? Cu1 O3A 1.972(3) . ? Cu1 O4A 1.977(3) 2 ? Cu1 N1 2.157(4) . ? Cu1 Cu1 2.6932(11) 2 ? O1 C24 1.256(5) . ? O1 Cu2 1.960(3) . ? N1 C1 1.337(6) . ? N1 N2 1.358(5) . ? C1 C2 1.402(6) . ? C1 C8 1.498(6) . ? O1SA C3SA 1.236(6) . ? N1SA C3SA 1.305(7) . ? N1SA C2SA 1.442(8) . ? N1SA C1SA 1.460(7) . ? C1SA H1SG 0.9800 . ? C1SA H1SH 0.9800 . ? C1SA H1SI 0.9800 . ? O1SB C3SB 1.237(6) . ? N1SB C3SB 1.343(7) . ? N1SB C1SB 1.444(7) . ? N1SB C2SB 1.461(6) . ? C1SB H1SD 0.9800 . ? C1SB H1SE 0.9800 . ? C1SB H1SF 0.9800 . ? O1S C3S 1.234(7) . ? N1S C3S 1.310(8) . ? N1S C1S 1.436(8) . ? N1S C2S 1.437(10) . ? C1S H1SC 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SA 0.9800 . ? O1SC C3SC 1.209(13) . ? N1SC C3SC 1.345(16) . ? N1SC C1SC 1.390(19) . ? N1SC C2SC 1.425(16) . ? C1SC H1SL 0.9800 . ? C1SC H1SK 0.9800 . ? C1SC H1SJ 0.9800 . ? O1SE C3SE 1.253(16) . ? N1SE C3SE 1.29(2) . ? N1SE C1SE 1.45(2) . ? N1SE C2SE 1.53(2) . ? C1SE H1SP 0.9800 . ? C1SE H1SQ 0.9800 . ? C1SE H1SR 0.9800 . ? O1SF C3SF 1.056(14) . ? N1SF C3SF 1.328(14) . ? N1SF C1SF 1.418(11) . ? N1SF C2SF 1.490(14) . ? C1SF H1SU 0.9800 . ? C1SF H1ST 0.9800 . ? C1SF H1SS 0.9800 . ? O1SD C3SD 1.131(12) . ? N1SD C3SD 1.366(15) . ? N1SD C2SD 1.455(15) . ? N1SD C1SD 1.457(14) . ? C1SD H1SO 0.9800 . ? C1SD H1SN 0.9800 . ? C1SD H1SM 0.9800 . ? O1A C24A 1.263(6) . ? O1A Cu2 1.981(3) 1_654 ? Cu2 O2A 1.971(3) 2_565 ? Cu2 O2 1.971(3) 2_466 ? Cu2 O1A 1.981(3) 1_456 ? Cu2 N3 2.142(4) 2_566 ? Cu2 Cu2 2.6821(11) 2_466 ? N2 C3 1.344(6) . ? N2 H2A 0.8800 . ? C2 C3 1.375(6) . ? C2 C7 1.517(6) . ? C2SA H2SD 0.9800 . ? C2SA H2SE 0.9800 . ? C2SA H2SF 0.9800 . ? C2SB H2SG 0.9800 . ? C2SB H2SH 0.9800 . ? C2SB H2SI 0.9800 . ? C2S H2SC 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SA 0.9800 . ? C2SC H2SL 0.9800 . ? C2SC H2SK 0.9800 . ? C2SC H2SJ 0.9800 . ? C2SE H2SP 0.9800 . ? C2SE H2SQ 0.9800 . ? C2SE H2SR 0.9800 . ? C2SF H2SU 0.9800 . ? C2SF H2ST 0.9800 . ? C2SF H2SS 0.9800 . ? C2SD H2SO 0.9800 . ? C2SD H2SN 0.9800 . ? C2SD H2SM 0.9800 . ? O2A C24A 1.260(6) . ? O2A Cu2 1.971(3) 2_565 ? O2 C24 1.271(5) . ? O2 Cu2 1.971(3) 2_466 ? O3 C25 1.260(5) . ? O3A C25A 1.271(5) . ? C3 C9 1.502(6) . ? C3SA H3SA 0.9500 . ? C3SB H3SB 0.9500 . ? C3S H3S 0.9500 . ? C3SC H3SC 0.9500 . ? C3SE H3SE 0.9500 . ? C3SF H3SF 0.9500 . ? C3SD H3SD 0.9500 . ? N3 C4 1.331(6) . ? N3 N4 1.357(5) . ? N3 Cu2 2.142(4) 2_566 ? O4 C25 1.269(5) . ? O4 Cu1 1.970(3) 2 ? O4A C25A 1.264(5) . ? O4A Cu1 1.977(3) 2 ? C4 C5 1.407(6) . ? C4 C10 1.492(6) . ? N4 C6 1.350(6) . ? N4 H4A 0.8800 . ? O5 C21 1.374(5) . ? O5 C15 1.394(5) . ? O5A C15A 1.399(6) . ? O5A C21A 1.401(6) . ? C5 C6 1.365(7) . ? C5 C7 1.500(6) . ? C6 C11 1.493(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.385(6) . ? C12 C13 1.387(6) . ? C12 C24 1.495(6) . ? C12A C17A 1.385(7) . ? C12A C13A 1.390(7) . ? C12A C24A 1.503(7) . ? C13 C14 1.388(6) . ? C13 H13B 0.9500 . ? C13A C14A 1.374(7) . ? C13A H14A 0.9500 . ? C14 C15 1.376(7) . ? C14 H14B 0.9500 . ? C14A C15A 1.374(7) . ? C14A H14C 0.9500 . ? C15 C16 1.396(7) . ? C15A C16A 1.369(7) . ? C16 C17 1.381(7) . ? C16 H16B 0.9500 . ? C16A C17A 1.386(7) . ? C16A H16A 0.9500 . ? C17 H17B 0.9500 . ? C17A H17A 0.9500 . ? C18 C19 1.396(6) . ? C18 C23 1.403(6) . ? C18 C25 1.489(6) . ? C18A C23A 1.389(6) . ? C18A C19A 1.394(7) . ? C18A C25A 1.495(7) . ? C19 C20 1.375(6) . ? C19 H19B 0.9500 . ? C19A C20A 1.387(6) . ? C19A H19A 0.9500 . ? C20 C21 1.384(6) . ? C20 H20B 0.9500 . ? C20A C21A 1.381(7) . ? C20A H20A 0.9500 . ? C21 C22 1.395(6) . ? C21A C22A 1.381(7) . ? C22 C23 1.380(6) . ? C22 H22B 0.9500 . ? C22A C23A 1.374(7) . ? C22A H22A 0.9500 . ? C23 H23B 0.9500 . ? C23A H23A 0.9500 . ? 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 Cu1 O4 167.05(13) . 2 ? O3 Cu1 O3A 90.55(13) . . ? O4 Cu1 O3A 88.08(13) 2 . ? O3 Cu1 O4A 87.81(13) . 2 ? O4 Cu1 O4A 90.69(13) 2 2 ? O3A Cu1 O4A 167.25(13) . 2 ? O3 Cu1 N1 98.77(14) . . ? O4 Cu1 N1 94.17(14) 2 . ? O3A Cu1 N1 94.27(14) . . ? O4A Cu1 N1 98.47(14) 2 . ? O3 Cu1 Cu1 82.30(10) . 2 ? O4 Cu1 Cu1 84.77(9) 2 2 ? O3A Cu1 Cu1 80.81(10) . 2 ? O4A Cu1 Cu1 86.44(9) 2 2 ? N1 Cu1 Cu1 174.99(11) . 2 ? C24 O1 Cu2 121.7(3) . . ? C1 N1 N2 105.5(4) . . ? C1 N1 Cu1 132.4(3) . . ? N2 N1 Cu1 121.7(3) . . ? N1 C1 C2 110.0(4) . . ? N1 C1 C8 119.8(4) . . ? C2 C1 C8 130.2(4) . . ? C3SA N1SA C2SA 121.0(5) . . ? C3SA N1SA C1SA 121.3(6) . . ? C2SA N1SA C1SA 117.4(5) . . ? N1SA C1SA H1SG 109.5 . . ? N1SA C1SA H1SH 109.5 . . ? H1SG C1SA H1SH 109.5 . . ? N1SA C1SA H1SI 109.5 . . ? H1SG C1SA H1SI 109.5 . . ? H1SH C1SA H1SI 109.5 . . ? C3SB N1SB C1SB 122.7(5) . . ? C3SB N1SB C2SB 119.8(5) . . ? C1SB N1SB C2SB 117.0(4) . . ? N1SB C1SB H1SD 109.5 . . ? N1SB C1SB H1SE 109.5 . . ? H1SD C1SB H1SE 109.5 . . ? N1SB C1SB H1SF 109.5 . . ? H1SD C1SB H1SF 109.5 . . ? H1SE C1SB H1SF 109.5 . . ? C3S N1S C1S 122.2(6) . . ? C3S N1S C2S 121.7(7) . . ? C1S N1S C2S 116.0(6) . . ? C3SC N1SC C1SC 120.5(12) . . ? C3SC N1SC C2SC 116.4(11) . . ? C1SC N1SC C2SC 122.4(12) . . ? N1SC C1SC H1SL 109.5 . . ? N1SC C1SC H1SK 109.5 . . ? H1SL C1SC H1SK 109.5 . . ? N1SC C1SC H1SJ 109.5 . . ? H1SL C1SC H1SJ 109.5 . . ? H1SK C1SC H1SJ 109.5 . . ? C3SE N1SE C1SE 131.5(17) . . ? C3SE N1SE C2SE 115.4(15) . . ? C1SE N1SE C2SE 113.1(16) . . ? N1SE C1SE H1SP 109.5 . . ? N1SE C1SE H1SQ 109.5 . . ? H1SP C1SE H1SQ 109.5 . . ? N1SE C1SE H1SR 109.5 . . ? H1SP C1SE H1SR 109.5 . . ? H1SQ C1SE H1SR 109.5 . . ? C3SF N1SF C1SF 121.3(9) . . ? C3SF N1SF C2SF 118.8(9) . . ? C1SF N1SF C2SF 119.5(9) . . ? C3SD N1SD C2SD 121.7(10) . . ? C3SD N1SD C1SD 121.2(10) . . ? C2SD N1SD C1SD 116.7(10) . . ? C24A O1A Cu2 129.6(3) . 1_654 ? O1 Cu2 O2A 88.98(14) . 2_565 ? O1 Cu2 O2 166.81(13) . 2_466 ? O2A Cu2 O2 88.23(14) 2_565 2_466 ? O1 Cu2 O1A 88.96(14) . 1_456 ? O2A Cu2 O1A 167.27(14) 2_565 1_456 ? O2 Cu2 O1A 90.94(14) 2_466 1_456 ? O1 Cu2 N3 97.19(14) . 2_566 ? O2A Cu2 N3 99.87(15) 2_565 2_566 ? O2 Cu2 N3 95.99(14) 2_466 2_566 ? O1A Cu2 N3 92.85(15) 1_456 2_566 ? O1 Cu2 Cu2 85.80(10) . 2_466 ? O2A Cu2 Cu2 89.12(10) 2_565 2_466 ? O2 Cu2 Cu2 81.26(10) 2_466 2_466 ? O1A Cu2 Cu2 78.21(10) 1_456 2_466 ? N3 Cu2 Cu2 170.55(12) 2_566 2_466 ? C3 N2 N1 111.9(4) . . ? C3 N2 H2A 124.0 . . ? N1 N2 H2A 124.0 . . ? C3 C2 C1 105.9(4) . . ? C3 C2 C7 127.8(4) . . ? C1 C2 C7 126.2(4) . . ? N1SA C2SA H2SD 109.5 . . ? N1SA C2SA H2SE 109.5 . . ? H2SD C2SA H2SE 109.5 . . ? N1SA C2SA H2SF 109.5 . . ? H2SD C2SA H2SF 109.5 . . ? H2SE C2SA H2SF 109.5 . . ? N1SB C2SB H2SG 109.5 . . ? N1SB C2SB H2SH 109.5 . . ? H2SG C2SB H2SH 109.5 . . ? N1SB C2SB H2SI 109.5 . . ? H2SG C2SB H2SI 109.5 . . ? H2SH C2SB H2SI 109.5 . . ? N1SC C2SC H2SL 109.5 . . ? N1SC C2SC H2SK 109.5 . . ? H2SL C2SC H2SK 109.5 . . ? N1SC C2SC H2SJ 109.5 . . ? H2SL C2SC H2SJ 109.5 . . ? H2SK C2SC H2SJ 109.5 . . ? N1SE C2SE H2SP 109.5 . . ? N1SE C2SE H2SQ 109.5 . . ? H2SP C2SE H2SQ 109.5 . . ? N1SE C2SE H2SR 109.5 . . ? H2SP C2SE H2SR 109.5 . . ? H2SQ C2SE H2SR 109.5 . . ? C24A O2A Cu2 117.1(3) . 2_565 ? C24 O2 Cu2 126.2(3) . 2_466 ? C25 O3 Cu1 125.0(3) . . ? C25A O3A Cu1 126.8(3) . . ? N2 C3 C2 106.6(4) . . ? N2 C3 C9 121.4(4) . . ? C2 C3 C9 132.0(4) . . ? O1SA C3SA N1SA 126.9(6) . . ? O1SA C3SA H3SA 116.6 . . ? N1SA C3SA H3SA 116.6 . . ? O1SB C3SB N1SB 123.8(5) . . ? O1SB C3SB H3SB 118.1 . . ? N1SB C3SB H3SB 118.1 . . ? O1S C3S N1S 125.5(6) . . ? O1S C3S H3S 117.2 . . ? N1S C3S H3S 117.2 . . ? O1SC C3SC N1SC 127.5(13) . . ? O1SC C3SC H3SC 116.3 . . ? N1SC C3SC H3SC 116.3 . . ? O1SE C3SE N1SE 156.6(16) . . ? O1SE C3SE H3SE 101.7 . . ? N1SE C3SE H3SE 101.7 . . ? O1SF C3SF N1SF 115.9(14) . . ? O1SF C3SF H3SF 122.1 . . ? N1SF C3SF H3SF 122.1 . . ? O1SD C3SD N1SD 127.4(12) . . ? O1SD C3SD H3SD 116.3 . . ? N1SD C3SD H3SD 116.3 . . ? C4 N3 N4 104.6(4) . . ? C4 N3 Cu2 130.2(3) . 2_566 ? N4 N3 Cu2 124.7(3) . 2_566 ? C25 O4 Cu1 121.7(3) . 2 ? C25A O4A Cu1 120.0(3) . 2 ? N3 C4 C5 111.1(4) . . ? N3 C4 C10 121.5(4) . . ? C5 C4 C10 127.5(4) . . ? C6 N4 N3 112.3(4) . . ? C6 N4 H4A 123.8 . . ? N3 N4 H4A 123.8 . . ? C21 O5 C15 118.0(4) . . ? C15A O5A C21A 116.9(4) . . ? C6 C5 C4 105.4(4) . . ? C6 C5 C7 127.9(4) . . ? C4 C5 C7 126.5(4) . . ? N4 C6 C5 106.7(4) . . ? N4 C6 C11 121.6(5) . . ? C5 C6 C11 131.7(5) . . ? C5 C7 C2 113.3(4) . . ? C5 C7 H7A 108.9 . . ? C2 C7 H7A 108.9 . . ? C5 C7 H7B 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 119.7(4) . . ? C17 C12 C24 120.5(4) . . ? C13 C12 C24 119.8(4) . . ? C17A C12A C13A 118.3(5) . . ? C17A C12A C24A 121.0(4) . . ? C13A C12A C24A 120.6(5) . . ? C12 C13 C14 120.4(5) . . ? C12 C13 H13B 119.8 . . ? C14 C13 H13B 119.8 . . ? C14A C13A C12A 121.3(5) . . ? C14A C13A H14A 119.3 . . ? C12A C13A H14A 119.3 . . ? C15 C14 C13 119.3(5) . . ? C15 C14 H14B 120.3 . . ? C13 C14 H14B 120.3 . . ? C13A C14A C15A 119.1(5) . . ? C13A C14A H14C 120.4 . . ? C15A C14A H14C 120.4 . . ? C14 C15 O5 121.1(4) . . ? C14 C15 C16 121.0(5) . . ? O5 C15 C16 117.8(4) . . ? C16A C15A C14A 121.1(5) . . ? C16A C15A O5A 117.6(5) . . ? C14A C15A O5A 121.2(5) . . ? C17 C16 C15 119.0(5) . . ? C17 C16 H16B 120.5 . . ? C15 C16 H16B 120.5 . . ? C15A C16A C17A 119.5(5) . . ? C15A C16A H16A 120.3 . . ? C17A C16A H16A 120.3 . . ? C16 C17 C12 120.6(5) . . ? C16 C17 H17B 119.7 . . ? C12 C17 H17B 119.7 . . ? C12A C17A C16A 120.6(5) . . ? C12A C17A H17A 119.7 . . ? C16A C17A H17A 119.7 . . ? C19 C18 C23 118.3(4) . . ? C19 C18 C25 120.8(4) . . ? C23 C18 C25 120.8(4) . . ? C23A C18A C19A 118.8(5) . . ? C23A C18A C25A 119.8(4) . . ? C19A C18A C25A 121.4(4) . . ? C20 C19 C18 121.3(4) . . ? C20 C19 H19B 119.3 . . ? C18 C19 H19B 119.3 . . ? C20A C19A C18A 120.3(5) . . ? C20A C19A H19A 119.8 . . ? C18A C19A H19A 119.8 . . ? C19 C20 C21 119.6(5) . . ? C19 C20 H20B 120.2 . . ? C21 C20 H20B 120.2 . . ? C21A C20A C19A 119.1(5) . . ? C21A C20A H20A 120.4 . . ? C19A C20A H20A 120.4 . . ? O5 C21 C20 123.6(4) . . ? O5 C21 C22 116.0(4) . . ? C20 C21 C22 120.4(4) . . ? C20A C21A C22A 121.6(5) . . ? C20A C21A O5A 117.6(5) . . ? C22A C21A O5A 120.7(4) . . ? C23 C22 C21 119.6(4) . . ? C23 C22 H22B 120.2 . . ? C21 C22 H22B 120.2 . . ? C23A C22A C21A 118.6(5) . . ? C23A C22A H22A 120.7 . . ? C21A C22A H22A 120.7 . . ? C22 C23 C18 120.7(4) . . ? C22 C23 H23B 119.7 . . ? C18 C23 H23B 119.7 . . ? C22A C23A C18A 121.6(5) . . ? C22A C23A H23A 119.2 . . ? C18A C23A H23A 119.2 . . ? O1 C24 O2 125.0(4) . . ? O1 C24 C12 118.4(4) . . ? O2 C24 C12 116.6(4) . . ? O2A C24A O1A 125.9(5) . . ? O2A C24A C12A 118.4(4) . . ? O1A C24A C12A 115.7(4) . . ? O4A C25A O3A 125.7(4) . . ? O4A C25A C18A 118.0(4) . . ? O3A C25A C18A 116.3(4) . . ? O3 C25 O4 125.7(4) . . ? O3 C25 C18 117.0(4) . . ? O4 C25 C18 117.3(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.809 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.092 # Attachment 'OBA-Ni.cif' data_10ag002_0m _database_code_depnum_ccdc_archive 'CCDC 790294' #TrackingRef 'OBA-Ni.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29.88 H37.38 N5.63 Ni O7.63' _chemical_formula_weight 655.99 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 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 14.7437(8) _cell_length_b 24.7090(13) _cell_length_c 20.6058(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.314(2) _cell_angle_gamma 90.00 _cell_volume 7240.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2327 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 26.21 _exptl_crystal_description Plate _exptl_crystal_colour Green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 0.585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.778611 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0614 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 42281 _diffrn_reflns_av_R_equivalents 0.1050 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6384 _reflns_number_gt 4308 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0845P)^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 6384 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 Ni1 Ni -0.74404(3) 0.170686(17) 0.08003(2) 0.02345(16) Uani 1 1 d . . . O1 O -0.81066(16) 0.24783(9) 0.08087(12) 0.0263(6) Uani 1 1 d . . . N1 N -0.6066(2) 0.19270(11) 0.08939(15) 0.0271(7) Uani 1 1 d . . . O2 O -0.89120(16) 0.17198(9) 0.06871(12) 0.0268(6) Uani 1 1 d . . . N2 N -0.5841(2) 0.24545(11) 0.08105(14) 0.0261(7) Uani 1 1 d . . . H222 H -0.6250 0.2706 0.0676 0.031 Uiso 1 1 calc R . . N3 N -0.2764(2) 0.16271(11) 0.31811(14) 0.0258(7) Uani 1 1 d . . . N4 N -0.2506(2) 0.11670(12) 0.29210(15) 0.0377(8) Uani 1 1 d . . . H444 H -0.2253 0.0893 0.3158 0.045 Uiso 1 1 calc R . . O3 O -1.23885(16) 0.58901(9) 0.07412(12) 0.0274(6) Uani 1 1 d . . . O4 O -1.2708(3) 0.57548(11) -0.03683(14) 0.0654(10) Uani 1 1 d . . . O5 O -1.22673(19) 0.33248(10) 0.06314(17) 0.0470(8) Uani 1 1 d . . . C1 C -0.5235(3) 0.16745(14) 0.11037(18) 0.0287(8) Uani 1 1 d . . . C2 C -0.4487(2) 0.20380(14) 0.11529(17) 0.0246(8) Uani 1 1 d . . . C3 C -0.4901(2) 0.25352(14) 0.09628(17) 0.0250(8) Uani 1 1 d . . . C4 C -0.3128(2) 0.19421(14) 0.26499(18) 0.0282(8) Uani 1 1 d . . . C5 C -0.3099(2) 0.16820(14) 0.20478(18) 0.0266(8) Uani 1 1 d . . . C6 C -0.2694(3) 0.11899(16) 0.22434(19) 0.0385(10) Uani 1 1 d . . . C7 C -0.3458(3) 0.19058(16) 0.13511(18) 0.0338(9) Uani 1 1 d . . . H7B H -0.3333 0.1645 0.1034 0.041 Uiso 1 1 calc R . . H7A H -0.3108 0.2232 0.1315 0.041 Uiso 1 1 calc R . . C8 C -0.5181(3) 0.10800(15) 0.1250(2) 0.0412(10) Uani 1 1 d . . . H8C H -0.5789 0.0950 0.1263 0.062 Uiso 1 1 calc R . . H8B H -0.4738 0.1016 0.1677 0.062 Uiso 1 1 calc R . . H8A H -0.4980 0.0893 0.0904 0.062 Uiso 1 1 calc R . . C9 C -0.4507(3) 0.30866(15) 0.09227(19) 0.0367(10) Uani 1 1 d . . . H9C H -0.4905 0.3280 0.0551 0.055 Uiso 1 1 calc R . . H9B H -0.3887 0.3056 0.0859 0.055 Uiso 1 1 calc R . . H9A H -0.4476 0.3279 0.1332 0.055 Uiso 1 1 calc R . . C10 C -0.3485(3) 0.24989(15) 0.2729(2) 0.0471(11) Uani 1 1 d . . . H10C H -0.3409 0.2573 0.3197 0.071 Uiso 1 1 calc R . . H10B H -0.4139 0.2521 0.2493 0.071 Uiso 1 1 calc R . . H10A H -0.3136 0.2759 0.2546 0.071 Uiso 1 1 calc R . . C11 C -0.2451(5) 0.0731(2) 0.1842(2) 0.093(2) Uani 1 1 d . . . H11C H -0.2180 0.0440 0.2139 0.140 Uiso 1 1 calc R . . H11B H -0.2008 0.0853 0.1606 0.140 Uiso 1 1 calc R . . H11A H -0.3011 0.0606 0.1523 0.140 Uiso 1 1 calc R . . C12 C -0.9763(2) 0.25319(13) 0.07048(17) 0.0245(8) Uani 1 1 d . . . C13 C -1.0587(3) 0.22562(14) 0.06946(18) 0.0300(9) Uani 1 1 d . . . H13 H -1.0581 0.1880 0.0708 0.036 Uiso 1 1 calc R . . C14 C -1.1414(3) 0.25292(14) 0.06643(19) 0.0313(9) Uani 1 1 d . . . H14 H -1.1964 0.2341 0.0653 0.038 Uiso 1 1 calc R . . C15 C -1.1408(2) 0.30865(14) 0.06511(19) 0.0296(9) Uani 1 1 d . . . C16 C -1.0607(3) 0.33766(14) 0.0649(2) 0.0358(10) Uani 1 1 d . . . H16 H -1.0620 0.3753 0.0626 0.043 Uiso 1 1 calc R . . C17 C -0.9788(2) 0.30955(14) 0.06826(18) 0.0285(8) Uani 1 1 d . . . H17 H -0.9241 0.3286 0.0690 0.034 Uiso 1 1 calc R . . C18 C -1.2465(3) 0.49913(14) 0.03476(19) 0.0293(9) Uani 1 1 d . . . C19 C -1.2768(3) 0.46383(15) -0.0189(2) 0.0401(10) Uani 1 1 d . . . H19 H -1.3015 0.4777 -0.0619 0.048 Uiso 1 1 calc R . . C20 C -1.2709(3) 0.40846(15) -0.0099(2) 0.0388(10) Uani 1 1 d . . . H20 H -1.2917 0.3850 -0.0460 0.047 Uiso 1 1 calc R . . C21 C -1.2337(3) 0.38915(15) 0.0538(2) 0.0374(10) Uani 1 1 d . . . C22 C -1.2050(3) 0.42254(15) 0.1088(2) 0.0426(11) Uani 1 1 d . . . H22 H -1.1811 0.4084 0.1517 0.051 Uiso 1 1 calc R . . C23 C -1.2126(3) 0.47833(15) 0.0983(2) 0.0380(10) Uani 1 1 d . . . H23 H -1.1945 0.5017 0.1348 0.046 Uiso 1 1 calc R . . C24 C -0.8890(3) 0.22301(14) 0.07354(17) 0.0252(8) Uani 1 1 d . . . C25 C -1.2536(3) 0.55902(15) 0.0232(2) 0.0340(9) Uani 1 1 d . . . N1S N 0.3945(9) 0.0490(5) -0.1371(7) 0.234(5) Uiso 1 1 d . . . C1S C 0.3024(11) 0.0783(6) -0.1761(8) 0.124(5) Uiso 0.50 1 d P A 1 H1SA H 0.2645 0.0861 -0.1458 0.187 Uiso 0.50 1 calc PR A 1 H1SB H 0.2679 0.0554 -0.2117 0.187 Uiso 0.50 1 calc PR A 1 H1SC H 0.3181 0.1115 -0.1948 0.187 Uiso 0.50 1 calc PR A 1 O1S O 0.4832(7) 0.0196(4) -0.0448(5) 0.232(4) Uiso 1 1 d . A 1 C2S C 0.4509(9) 0.0377(5) -0.1910(6) 0.204(5) Uiso 1 1 d . A 1 H2SA H 0.5018 0.0132 -0.1724 0.307 Uiso 1 1 calc R A 1 H2SB H 0.4756 0.0711 -0.2029 0.307 Uiso 1 1 calc R A 1 H2SC H 0.4097 0.0218 -0.2304 0.307 Uiso 1 1 calc R A 1 C3S C 0.4154(4) 0.0412(2) -0.0748(3) 0.0612(14) Uiso 1 1 d . A 1 H3SA H 0.3738 0.0536 -0.0512 0.073 Uiso 1 1 calc R A 1 C1S' C 0.3774(10) 0.0706(5) -0.2166(6) 0.092(4) Uiso 0.50 1 d P A 2 H1SD H 0.3467 0.1052 -0.2216 0.137 Uiso 0.50 1 calc PR A 2 H1SE H 0.3387 0.0451 -0.2467 0.137 Uiso 0.50 1 calc PR A 2 H1SF H 0.4369 0.0739 -0.2270 0.137 Uiso 0.50 1 calc PR A 2 O1W O -0.77464(18) 0.17815(12) -0.02503(13) 0.0270(6) Uiso 1 1 d . . . H1WB H -0.748(4) 0.198(2) -0.050(3) 0.089(18) Uiso 1 1 d . . . H1WA H -0.784(5) 0.152(3) -0.038(3) 0.13(3) 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 0.0221(3) 0.0209(3) 0.0260(3) 0.0015(2) 0.0041(2) 0.00151(19) O1 0.0237(14) 0.0246(13) 0.0309(14) 0.0042(11) 0.0078(11) 0.0024(11) N1 0.0238(17) 0.0253(16) 0.0307(18) 0.0065(13) 0.0045(14) 0.0032(13) O2 0.0262(14) 0.0220(13) 0.0315(14) 0.0035(11) 0.0062(11) 0.0021(11) N2 0.0250(17) 0.0242(16) 0.0271(17) 0.0041(13) 0.0035(14) 0.0046(13) N3 0.0273(17) 0.0212(16) 0.0260(17) -0.0019(13) 0.0021(14) -0.0004(12) N4 0.051(2) 0.0288(18) 0.0272(18) 0.0025(14) 0.0003(16) 0.0146(16) O3 0.0298(14) 0.0200(12) 0.0316(15) -0.0008(11) 0.0067(12) 0.0026(11) O4 0.134(3) 0.0292(16) 0.0275(17) -0.0010(13) 0.0120(19) -0.0018(18) O5 0.0356(16) 0.0192(13) 0.094(2) 0.0008(14) 0.0314(16) 0.0058(12) C1 0.028(2) 0.032(2) 0.026(2) 0.0017(16) 0.0072(17) 0.0072(17) C2 0.0158(18) 0.036(2) 0.0216(19) 0.0011(16) 0.0048(15) 0.0030(15) C3 0.022(2) 0.034(2) 0.0181(19) 0.0056(15) 0.0038(15) -0.0007(16) C4 0.023(2) 0.0293(19) 0.031(2) 0.0040(17) 0.0059(17) 0.0002(16) C5 0.0204(19) 0.032(2) 0.028(2) 0.0010(17) 0.0059(16) -0.0011(16) C6 0.047(3) 0.041(2) 0.024(2) -0.0032(18) 0.0026(19) 0.016(2) C7 0.025(2) 0.046(2) 0.029(2) 0.0015(18) 0.0046(17) 0.0021(17) C8 0.029(2) 0.032(2) 0.057(3) 0.007(2) 0.002(2) 0.0046(18) C9 0.039(2) 0.040(2) 0.030(2) 0.0082(18) 0.0064(19) -0.0009(19) C10 0.068(3) 0.035(2) 0.034(2) 0.0030(19) 0.005(2) 0.016(2) C11 0.163(6) 0.071(4) 0.034(3) -0.010(3) 0.007(3) 0.065(4) C12 0.025(2) 0.0216(18) 0.026(2) 0.0002(15) 0.0039(16) 0.0033(15) C13 0.033(2) 0.0196(18) 0.040(2) 0.0018(16) 0.0150(18) 0.0019(16) C14 0.028(2) 0.0231(19) 0.046(2) 0.0010(17) 0.0142(18) 0.0004(16) C15 0.023(2) 0.0239(18) 0.044(2) 0.0006(17) 0.0112(18) 0.0044(16) C16 0.035(2) 0.0202(19) 0.056(3) 0.0022(18) 0.018(2) 0.0042(16) C17 0.025(2) 0.0235(18) 0.039(2) 0.0006(16) 0.0123(18) -0.0021(15) C18 0.027(2) 0.0270(19) 0.034(2) -0.0037(17) 0.0085(18) 0.0024(16) C19 0.052(3) 0.034(2) 0.034(2) -0.0064(18) 0.010(2) 0.001(2) C20 0.044(3) 0.029(2) 0.048(3) -0.0085(19) 0.022(2) -0.0016(18) C21 0.029(2) 0.0217(19) 0.068(3) -0.003(2) 0.024(2) 0.0011(17) C22 0.043(3) 0.029(2) 0.055(3) 0.010(2) 0.010(2) 0.0085(19) C23 0.038(2) 0.025(2) 0.048(3) -0.0035(19) 0.008(2) 0.0051(18) C24 0.029(2) 0.0240(19) 0.024(2) 0.0008(15) 0.0084(16) 0.0009(16) C25 0.038(2) 0.027(2) 0.036(2) 0.0007(18) 0.0088(19) 0.0043(17) _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 O3 2.024(2) 3_545 ? Ni1 N3 2.050(3) 2_455 ? Ni1 N1 2.058(3) . ? Ni1 O1W 2.100(3) . ? Ni1 O2 2.120(2) . ? Ni1 O1 2.147(2) . ? Ni1 C24 2.472(3) . ? O1 C24 1.281(4) . ? N1 C1 1.340(4) . ? N1 N2 1.367(4) . ? O2 C24 1.265(4) . ? N2 C3 1.351(4) . ? N2 H222 0.8600 . ? N3 C4 1.335(4) . ? N3 N4 1.354(4) . ? N3 Ni1 2.050(3) 2_455 ? N4 C6 1.351(5) . ? N4 H444 0.8600 . ? O3 C25 1.256(4) . ? O3 Ni1 2.024(2) 3_455 ? O4 C25 1.262(4) . ? O5 C15 1.388(4) . ? O5 C21 1.413(4) . ? C1 C2 1.405(5) . ? C1 C8 1.498(5) . ? C2 C3 1.382(5) . ? C2 C7 1.500(5) . ? C3 C9 1.492(5) . ? C4 C5 1.408(5) . ? C4 C10 1.497(5) . ? C5 C6 1.367(5) . ? C5 C7 1.499(5) . ? C6 C11 1.502(5) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 H8C 0.9600 . ? C8 H8B 0.9600 . ? C8 H8A 0.9600 . ? C9 H9C 0.9600 . ? C9 H9B 0.9600 . ? C9 H9A 0.9600 . ? C10 H10C 0.9600 . ? C10 H10B 0.9600 . ? C10 H10A 0.9600 . ? C11 H11C 0.9600 . ? C11 H11B 0.9600 . ? C11 H11A 0.9600 . ? C12 C13 1.387(5) . ? C12 C17 1.393(5) . ? C12 C24 1.474(5) . ? C13 C14 1.380(5) . ? C13 H13 0.9300 . ? C14 C15 1.377(5) . ? C14 H14 0.9300 . ? C15 C16 1.382(5) . ? C16 C17 1.379(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C23 1.372(5) . ? C18 C19 1.387(5) . ? C18 C25 1.498(5) . ? C19 C20 1.380(5) . ? C19 H19 0.9300 . ? C20 C21 1.369(6) . ? C20 H20 0.9300 . ? C21 C22 1.374(6) . ? C22 C23 1.395(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? N1S C3S 1.253(12) . ? N1S C1S 1.561(16) . ? N1S C2S 1.579(14) . ? N1S C1S' 1.678(17) . ? C1S H1SA 0.9600 . ? C1S H1SB 0.9600 . ? C1S H1SC 0.9600 . ? O1S C3S 1.157(9) . ? C2S H2SA 0.9600 . ? C2S H2SB 0.9600 . ? C2S H2SC 0.9600 . ? C3S H3SA 0.9300 . ? C1S' H1SD 0.9600 . ? C1S' H1SE 0.9600 . ? C1S' H1SF 0.9600 . ? O1W H1WB 0.88(6) . ? O1W H1WA 0.71(7) . ? 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 Ni1 N3 88.17(10) 3_545 2_455 ? O3 Ni1 N1 102.55(10) 3_545 . ? N3 Ni1 N1 93.14(11) 2_455 . ? O3 Ni1 O1W 91.54(10) 3_545 . ? N3 Ni1 O1W 176.17(11) 2_455 . ? N1 Ni1 O1W 90.66(11) . . ? O3 Ni1 O2 93.57(9) 3_545 . ? N3 Ni1 O2 89.05(10) 2_455 . ? N1 Ni1 O2 163.79(10) . . ? O1W Ni1 O2 87.15(10) . . ? O3 Ni1 O1 155.56(9) 3_545 . ? N3 Ni1 O1 91.20(10) 2_455 . ? N1 Ni1 O1 101.88(10) . . ? O1W Ni1 O1 87.48(10) . . ? O2 Ni1 O1 61.99(9) . . ? O3 Ni1 C24 124.34(10) 3_545 . ? N3 Ni1 C24 89.81(11) 2_455 . ? N1 Ni1 C24 133.09(11) . . ? O1W Ni1 C24 87.19(10) . . ? O2 Ni1 C24 30.78(10) . . ? O1 Ni1 C24 31.22(10) . . ? C24 O1 Ni1 88.53(19) . . ? C1 N1 N2 104.6(3) . . ? C1 N1 Ni1 134.5(2) . . ? N2 N1 Ni1 120.4(2) . . ? C24 O2 Ni1 90.1(2) . . ? C3 N2 N1 112.3(3) . . ? C3 N2 H222 123.9 . . ? N1 N2 H222 123.9 . . ? C4 N3 N4 105.0(3) . . ? C4 N3 Ni1 134.6(2) . 2_455 ? N4 N3 Ni1 120.4(2) . 2_455 ? C6 N4 N3 111.8(3) . . ? C6 N4 H444 124.1 . . ? N3 N4 H444 124.1 . . ? C25 O3 Ni1 129.6(2) . 3_455 ? C15 O5 C21 117.2(3) . . ? N1 C1 C2 111.0(3) . . ? N1 C1 C8 121.2(3) . . ? C2 C1 C8 127.8(3) . . ? C3 C2 C1 105.5(3) . . ? C3 C2 C7 127.6(3) . . ? C1 C2 C7 126.8(3) . . ? N2 C3 C2 106.5(3) . . ? N2 C3 C9 120.8(3) . . ? C2 C3 C9 132.7(3) . . ? N3 C4 C5 110.9(3) . . ? N3 C4 C10 121.6(3) . . ? C5 C4 C10 127.5(3) . . ? C6 C5 C4 105.0(3) . . ? C6 C5 C7 128.8(3) . . ? C4 C5 C7 126.2(3) . . ? N4 C6 C5 107.2(3) . . ? N4 C6 C11 121.6(4) . . ? C5 C6 C11 131.1(4) . . ? C5 C7 C2 114.6(3) . . ? C5 C7 H7B 108.6 . . ? C2 C7 H7B 108.6 . . ? C5 C7 H7A 108.6 . . ? C2 C7 H7A 108.6 . . ? H7B C7 H7A 107.6 . . ? C1 C8 H8C 109.5 . . ? C1 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? C1 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? C3 C9 H9C 109.5 . . ? C3 C9 H9B 109.5 . . ? H9C C9 H9B 109.5 . . ? C3 C9 H9A 109.5 . . ? H9C C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? C4 C10 H10C 109.5 . . ? C4 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C4 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? C6 C11 H11C 109.5 . . ? C6 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C6 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? C13 C12 C17 118.4(3) . . ? C13 C12 C24 120.2(3) . . ? C17 C12 C24 121.4(3) . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 118.6(3) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 121.9(3) . . ? C14 C15 O5 114.4(3) . . ? C16 C15 O5 123.6(3) . . ? C17 C16 C15 118.4(3) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C16 C17 C12 121.3(3) . . ? C16 C17 H17 119.3 . . ? C12 C17 H17 119.3 . . ? C23 C18 C19 119.0(4) . . ? C23 C18 C25 121.0(3) . . ? C19 C18 C25 120.0(3) . . ? C20 C19 C18 121.4(4) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 118.0(4) . . ? C21 C20 H20 121.0 . . ? C19 C20 H20 121.0 . . ? C20 C21 C22 122.6(4) . . ? C20 C21 O5 118.2(4) . . ? C22 C21 O5 119.2(4) . . ? C21 C22 C23 118.1(4) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C18 C23 C22 120.8(4) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O2 C24 O1 119.3(3) . . ? O2 C24 C12 119.8(3) . . ? O1 C24 C12 120.9(3) . . ? O2 C24 Ni1 59.08(17) . . ? O1 C24 Ni1 60.25(17) . . ? C12 C24 Ni1 178.7(3) . . ? O3 C25 O4 125.1(3) . . ? O3 C25 C18 117.4(3) . . ? O4 C25 C18 117.5(3) . . ? C3S N1S C1S 123.0(12) . . ? C3S N1S C2S 131.3(11) . . ? C1S N1S C2S 105.5(12) . . ? C3S N1S C1S' 169.1(11) . . ? C1S N1S C1S' 57.5(8) . . ? C2S N1S C1S' 48.8(7) . . ? N1S C1S H1SA 109.5 . . ? N1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? N1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? N1S C2S H2SA 109.5 . . ? N1S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? N1S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? O1S C3S N1S 124.2(9) . . ? O1S C3S H3SA 117.9 . . ? N1S C3S H3SA 117.9 . . ? N1S C1S' H1SD 109.5 . . ? N1S C1S' H1SE 109.5 . . ? H1SD C1S' H1SE 109.5 . . ? N1S C1S' H1SF 109.5 . . ? H1SD C1S' H1SF 109.5 . . ? H1SE C1S' H1SF 109.5 . . ? Ni1 O1W H1WB 131(3) . . ? Ni1 O1W H1WA 106(6) . . ? H1WB O1W H1WA 112(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.599 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.078 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.002 967.7 271.3 2 0.500 0.500 0.230 968.1 271.3 _platon_squeeze_details ; ; # Attachment '- OBA_Zn.cif' data_09tba030_0m _database_code_depnum_ccdc_archive 'CCDC 790295' #TrackingRef '- OBA_Zn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 N4 O5 Zn' _chemical_formula_weight 525.85 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P6(1)22 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+5/6' '-x+y, y, -z+1/2' 'x, x-y, -z+1/6' _cell_length_a 9.6491(2) _cell_length_b 9.6491(2) _cell_length_c 48.258(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3891.1(2) _cell_formula_units_Z 6 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8411 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.12 _exptl_crystal_description Cube _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.825458 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0852 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 44380 _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -57 _diffrn_reflns_limit_l_max 56 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.84 _reflns_number_total 2254 _reflns_number_gt 2159 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0466P)^2^+11.1861P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(4) _refine_ls_number_reflns 2254 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _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 Zn1 Zn 0.69881(6) 0.30119(6) 0.9167 0.0388(3) Uani 1 2 d S . . N1 N 0.5891(6) 0.0752(5) 0.92854(10) 0.0389(11) Uani 1 1 d . . . C1 C 0.5710(7) -0.0590(7) 0.91648(13) 0.0388(13) Uani 1 1 d . . . O1 O 0.7077(5) 0.4494(5) 0.94467(9) 0.0459(10) Uani 1 1 d . . . N2 N 0.4595(6) 0.0261(6) 0.94557(9) 0.0397(11) Uani 1 1 d . . . H2A H 0.4418 0.0891 0.9557 0.048 Uiso 1 1 calc R . . C2 C 0.4319(6) -0.1899(6) 0.92622(11) 0.0362(13) Uani 1 1 d . . . O2 O 0.4699(5) 0.3013(6) 0.96508(9) 0.0508(11) Uani 1 1 d . . . C3 C 0.3637(7) -0.1331(7) 0.94449(12) 0.0421(15) Uani 1 1 d . . . O3 O 0.6348(6) 1.0000 1.0000 0.0493(16) Uani 1 2 d S . . C7 C 0.3614(5) -0.3614(5) 0.9167 0.0418(19) Uani 1 2 d S . . H7A H 0.3657 -0.4254 0.9318 0.063 Uiso 0.50 1 calc PR . . H7B H 0.4254 -0.3657 0.9016 0.063 Uiso 0.50 1 calc PR . . C8 C 0.6888(8) -0.0514(8) 0.89599(14) 0.0521(17) Uani 1 1 d . . . H8A H 0.7602 0.0581 0.8910 0.078 Uiso 1 1 calc R . . H8B H 0.6337 -0.1112 0.8798 0.078 Uiso 1 1 calc R . . H8C H 0.7490 -0.0962 0.9039 0.078 Uiso 1 1 calc R . . C9 C 0.2133(8) -0.2138(9) 0.96170(14) 0.0593(19) Uani 1 1 d . . . H9A H 0.1982 -0.1341 0.9709 0.089 Uiso 1 1 calc R . . H9B H 0.2227 -0.2814 0.9753 0.089 Uiso 1 1 calc R . . H9C H 0.1233 -0.2773 0.9499 0.089 Uiso 1 1 calc R . . C12 C 0.6097(7) 0.5822(7) 0.97199(11) 0.0364(13) Uani 1 1 d . . . C13 C 0.7438(8) 0.7274(8) 0.96603(13) 0.0457(16) Uani 1 1 d . . . H13A H 0.8261 0.7301 0.9556 0.055 Uiso 1 1 calc R . . C14 C 0.7568(7) 0.8703(8) 0.97556(13) 0.0454(15) Uani 1 1 d . . . H14A H 0.8453 0.9683 0.9709 0.054 Uiso 1 1 calc R . . C15 C 0.6367(7) 0.8635(8) 0.99187(13) 0.0413(14) Uani 1 1 d . . . C16 C 0.5049(7) 0.7201(8) 0.99875(13) 0.0475(16) Uani 1 1 d . . . H16A H 0.4252 0.7174 1.0099 0.057 Uiso 1 1 calc R . . C17 C 0.4921(7) 0.5795(7) 0.98882(12) 0.0432(15) Uani 1 1 d . . . H17A H 0.4033 0.4820 0.9935 0.052 Uiso 1 1 calc R . . C18 C 0.5907(8) 0.4301(8) 0.95998(11) 0.0419(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0289(3) 0.0289(3) 0.0468(5) 0.0030(4) 0.0030(4) 0.0058(4) N1 0.027(3) 0.027(2) 0.047(3) 0.004(2) 0.001(2) 0.002(2) C1 0.029(3) 0.037(3) 0.042(3) 0.000(3) -0.006(3) 0.011(2) O1 0.036(2) 0.035(2) 0.060(3) -0.0042(18) 0.001(2) 0.013(2) N2 0.035(3) 0.036(3) 0.037(2) -0.003(2) 0.002(2) 0.009(2) C2 0.029(3) 0.032(3) 0.037(3) 0.001(2) -0.002(2) 0.007(2) O2 0.045(3) 0.038(3) 0.059(3) -0.005(2) 0.003(2) 0.014(2) C3 0.034(3) 0.029(3) 0.036(3) 0.001(2) 0.002(3) -0.004(3) O3 0.035(2) 0.039(3) 0.075(4) -0.006(3) -0.0031(15) 0.0195(17) C7 0.028(3) 0.028(3) 0.050(5) -0.004(3) -0.004(3) -0.001(3) C8 0.038(4) 0.036(3) 0.070(4) 0.004(3) 0.007(3) 0.009(3) C9 0.040(4) 0.055(4) 0.053(4) -0.003(3) 0.018(3) 0.001(3) C12 0.037(3) 0.029(3) 0.042(3) 0.003(2) 0.001(3) 0.016(3) C13 0.040(4) 0.047(4) 0.054(4) -0.004(3) 0.001(3) 0.024(3) C14 0.038(3) 0.032(3) 0.060(4) 0.003(3) 0.005(3) 0.012(3) C15 0.039(3) 0.038(3) 0.051(4) -0.001(3) -0.002(3) 0.022(3) C16 0.039(3) 0.049(4) 0.050(3) 0.000(3) 0.006(3) 0.018(3) C17 0.031(3) 0.037(4) 0.054(4) 0.006(3) -0.001(3) 0.011(3) C18 0.042(4) 0.044(4) 0.040(3) -0.002(3) -0.007(3) 0.022(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 Zn1 O1 1.938(4) . ? Zn1 O1 1.938(4) 10_666 ? Zn1 N1 1.974(4) . ? Zn1 N1 1.974(4) 10_666 ? N1 C1 1.348(8) . ? N1 N2 1.368(7) . ? C1 C2 1.387(8) . ? C1 C8 1.481(9) . ? O1 C18 1.282(7) . ? N2 C3 1.340(7) . ? N2 H2A 0.8600 . ? C2 C3 1.368(8) . ? C2 C7 1.512(7) . ? O2 C18 1.231(8) . ? C3 C9 1.507(8) . ? O3 C15 1.383(7) . ? O3 C15 1.383(7) 8_677 ? C7 C2 1.512(7) 10_556 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C12 C13 1.380(9) . ? C12 C17 1.385(8) . ? C12 C18 1.502(8) . ? C13 C14 1.399(9) . ? C13 H13A 0.9300 . ? C14 C15 1.375(8) . ? C14 H14A 0.9300 . ? C15 C16 1.372(9) . ? C16 C17 1.385(9) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O1 106.1(3) . 10_666 ? O1 Zn1 N1 114.47(19) . . ? O1 Zn1 N1 100.21(19) 10_666 . ? O1 Zn1 N1 100.21(19) . 10_666 ? O1 Zn1 N1 114.47(19) 10_666 10_666 ? N1 Zn1 N1 121.0(3) . 10_666 ? C1 N1 N2 105.6(5) . . ? C1 N1 Zn1 132.5(4) . . ? N2 N1 Zn1 116.7(4) . . ? N1 C1 C2 109.3(5) . . ? N1 C1 C8 120.9(5) . . ? C2 C1 C8 129.8(6) . . ? C18 O1 Zn1 125.7(4) . . ? C3 N2 N1 111.1(5) . . ? C3 N2 H2A 124.4 . . ? N1 N2 H2A 124.4 . . ? C3 C2 C1 107.0(5) . . ? C3 C2 C7 126.3(5) . . ? C1 C2 C7 126.5(5) . . ? N2 C3 C2 106.9(5) . . ? N2 C3 C9 120.3(6) . . ? C2 C3 C9 132.8(6) . . ? C15 O3 C15 121.4(7) . 8_677 ? C2 C7 C2 112.2(7) . 10_556 ? C2 C7 H7A 109.2 . . ? C2 C7 H7A 109.2 10_556 . ? C2 C7 H7B 109.2 . . ? C2 C7 H7B 109.2 10_556 . ? H7A C7 H7B 107.9 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C13 C12 C17 119.0(6) . . ? C13 C12 C18 120.4(6) . . ? C17 C12 C18 120.6(6) . . ? C12 C13 C14 120.6(6) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C15 C14 C13 118.9(6) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C16 C15 C14 121.4(6) . . ? C16 C15 O3 116.4(5) . . ? C14 C15 O3 122.0(6) . . ? C15 C16 C17 119.2(6) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? C12 C17 C16 120.9(6) . . ? C12 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? O2 C18 O1 125.6(6) . . ? O2 C18 C12 120.0(6) . . ? O1 C18 C12 114.3(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.84 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.682 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.069 data_11sg013_0m _database_code_depnum_ccdc_archive 'CCDC 838983' #TrackingRef 'DPA-Cu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H24 Cu N4 O4' _chemical_formula_weight 508.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 24.573(5) _cell_length_b 9.3013(17) _cell_length_c 21.788(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.754(7) _cell_angle_gamma 90.00 _cell_volume 4656.8(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5777 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.78 _exptl_crystal_description Needle _exptl_crystal_colour Green _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 0.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.808748 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.1428 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 36095 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.84 _reflns_number_total 6036 _reflns_number_gt 4281 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0507P)^2^+1.9905P] 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 6036 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.162948(11) 0.30295(3) 0.028807(12) 0.03574(10) Uani 1 1 d . . . O1 O 0.22173(7) 0.33332(15) 0.11702(8) 0.0426(4) Uani 1 1 d . . . N1 N 0.14457(8) 0.51087(18) 0.02120(8) 0.0371(4) Uani 1 1 d . . . C1 C 0.10779(9) 0.5965(2) -0.02403(10) 0.0361(5) Uani 1 1 d . . . N2 N 0.16405(8) 0.59008(18) 0.07705(9) 0.0392(4) Uani 1 1 d . . . H2A H 0.1880 0.5588 0.1138 0.047 Uiso 1 1 calc R . . C2 C 0.10430(9) 0.7307(2) 0.00379(11) 0.0357(5) Uani 1 1 d . . . O2 O 0.20512(8) 0.1746(2) 0.18359(10) 0.0710(6) Uani 1 1 d . . . C3 C 0.14133(9) 0.7240(2) 0.06802(11) 0.0367(5) Uani 1 1 d . . . N3 N -0.08531(8) 0.7692(2) -0.04739(9) 0.0386(4) Uani 1 1 d . . . O3 O 0.35073(8) 0.25211(18) 0.06559(8) 0.0513(4) Uani 1 1 d . . . C4 C -0.02900(9) 0.7873(2) -0.01138(11) 0.0379(5) Uani 1 1 d . . . N4 N -0.08978(8) 0.7938(2) -0.11003(10) 0.0422(4) Uani 1 1 d . . . H4A H -0.1218 0.7880 -0.1432 0.051 Uiso 1 1 calc R . . O4 O 0.30807(9) 0.39289(18) -0.01604(8) 0.0561(5) Uani 1 1 d . . . C5 C 0.00258(9) 0.8251(2) -0.05170(11) 0.0368(5) Uani 1 1 d . . . C6 C -0.03794(10) 0.8286(2) -0.11427(12) 0.0422(5) Uani 1 1 d . . . C7 C 0.06660(9) 0.8557(2) -0.03040(12) 0.0417(5) Uani 1 1 d . . . H7A H 0.0756 0.9377 -0.0010 0.050 Uiso 1 1 calc R . . H7B H 0.0760 0.8814 -0.0686 0.050 Uiso 1 1 calc R . . C8 C 0.07830(12) 0.5510(3) -0.09362(12) 0.0536(6) Uani 1 1 d . . . H8A H 0.0945 0.4614 -0.1009 0.080 Uiso 1 1 calc R . . H8B H 0.0841 0.6229 -0.1223 0.080 Uiso 1 1 calc R . . H8C H 0.0374 0.5393 -0.1025 0.080 Uiso 1 1 calc R . . C9 C 0.15783(12) 0.8334(3) 0.12157(13) 0.0530(6) Uani 1 1 d . . . H9A H 0.1897 0.7979 0.1584 0.079 Uiso 1 1 calc R . . H9B H 0.1252 0.8520 0.1348 0.079 Uiso 1 1 calc R . . H9C H 0.1692 0.9208 0.1060 0.079 Uiso 1 1 calc R . . C10 C -0.00698(11) 0.7715(3) 0.06173(12) 0.0524(6) Uani 1 1 d . . . H10A H -0.0393 0.7699 0.0767 0.079 Uiso 1 1 calc R . . H10B H 0.0179 0.8512 0.0814 0.079 Uiso 1 1 calc R . . H10C H 0.0145 0.6834 0.0739 0.079 Uiso 1 1 calc R . . C11 C -0.03191(12) 0.8615(4) -0.17882(14) 0.0683(8) Uani 1 1 d . . . H11A H -0.0442 0.7798 -0.2073 0.102 Uiso 1 1 calc R . . H11B H 0.0080 0.8827 -0.1720 0.102 Uiso 1 1 calc R . . H11C H -0.0557 0.9429 -0.1985 0.102 Uiso 1 1 calc R . . C12 C 0.30264(9) 0.2183(2) 0.19619(10) 0.0344(4) Uani 1 1 d . . . C13 C 0.32051(11) 0.0948(2) 0.23461(11) 0.0474(6) Uani 1 1 d . . . H13A H 0.2926 0.0331 0.2397 0.057 Uiso 1 1 calc R . . C14 C 0.37900(12) 0.0625(3) 0.26522(14) 0.0615(7) Uani 1 1 d . . . H14A H 0.3904 -0.0204 0.2903 0.074 Uiso 1 1 calc R . . C15 C 0.41988(12) 0.1546(3) 0.25796(14) 0.0621(7) Uani 1 1 d . . . H15A H 0.4592 0.1338 0.2784 0.075 Uiso 1 1 calc R . . C16 C 0.40327(10) 0.2772(3) 0.22080(12) 0.0502(6) Uani 1 1 d . . . H16A H 0.4317 0.3384 0.2166 0.060 Uiso 1 1 calc R . . C17 C 0.34461(9) 0.3120(2) 0.18925(10) 0.0351(4) Uani 1 1 d . . . C18 C 0.32936(9) 0.4561(2) 0.15632(10) 0.0353(5) Uani 1 1 d . . . C19 C 0.32286(10) 0.5684(2) 0.19504(12) 0.0452(5) Uani 1 1 d . . . H19A H 0.3275 0.5508 0.2386 0.054 Uiso 1 1 calc R . . C20 C 0.30954(11) 0.7063(3) 0.17004(15) 0.0544(7) Uani 1 1 d . . . H20A H 0.3063 0.7804 0.1972 0.065 Uiso 1 1 calc R . . C21 C 0.30117(11) 0.7341(2) 0.10529(15) 0.0528(6) Uani 1 1 d . . . H21A H 0.2922 0.8265 0.0884 0.063 Uiso 1 1 calc R . . C22 C 0.30624(10) 0.6230(2) 0.06582(12) 0.0442(5) Uani 1 1 d . . . H22A H 0.2996 0.6409 0.0218 0.053 Uiso 1 1 calc R . . C23 C 0.32107(9) 0.4842(2) 0.09053(11) 0.0356(4) Uani 1 1 d . . . C24 C 0.23822(9) 0.2436(2) 0.16365(11) 0.0372(5) Uani 1 1 d . . . C25 C 0.32651(9) 0.3708(2) 0.04524(11) 0.0371(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.04273(16) 0.03333(15) 0.03251(16) 0.00196(10) 0.01500(11) 0.00233(11) O1 0.0376(8) 0.0383(8) 0.0416(9) 0.0078(7) 0.0011(7) -0.0041(6) N1 0.0387(9) 0.0322(9) 0.0369(10) 0.0018(7) 0.0091(8) 0.0013(7) C1 0.0347(11) 0.0344(10) 0.0376(12) 0.0052(9) 0.0109(9) -0.0028(8) N2 0.0422(10) 0.0355(9) 0.0343(10) 0.0014(7) 0.0067(8) 0.0037(8) C2 0.0298(10) 0.0332(10) 0.0445(13) 0.0071(9) 0.0137(9) -0.0017(8) O2 0.0413(10) 0.1064(16) 0.0606(12) 0.0363(11) 0.0122(9) -0.0089(10) C3 0.0342(10) 0.0320(10) 0.0453(13) 0.0015(9) 0.0158(9) 0.0001(8) N3 0.0345(9) 0.0424(10) 0.0407(11) 0.0028(8) 0.0153(8) -0.0037(7) O3 0.0694(11) 0.0463(9) 0.0388(9) 0.0005(7) 0.0202(8) 0.0180(8) C4 0.0373(11) 0.0331(10) 0.0434(13) 0.0028(9) 0.0146(9) -0.0010(8) N4 0.0324(9) 0.0516(11) 0.0405(11) 0.0044(8) 0.0105(8) -0.0026(8) O4 0.0862(13) 0.0463(9) 0.0379(9) 0.0047(7) 0.0246(9) 0.0151(9) C5 0.0332(10) 0.0299(10) 0.0465(13) 0.0072(9) 0.0133(9) 0.0031(8) C6 0.0362(11) 0.0457(12) 0.0480(14) 0.0099(10) 0.0188(10) 0.0039(9) C7 0.0331(11) 0.0345(10) 0.0569(15) 0.0125(10) 0.0152(10) -0.0011(9) C8 0.0614(16) 0.0455(13) 0.0431(14) 0.0035(11) 0.0053(12) 0.0019(11) C9 0.0586(15) 0.0431(13) 0.0531(16) -0.0077(11) 0.0145(12) 0.0032(11) C10 0.0451(13) 0.0664(16) 0.0445(14) 0.0047(12) 0.0145(11) -0.0058(12) C11 0.0531(16) 0.102(2) 0.0528(17) 0.0267(16) 0.0230(13) 0.0036(16) C12 0.0378(11) 0.0357(11) 0.0277(10) -0.0016(8) 0.0092(8) 0.0027(8) C13 0.0545(14) 0.0410(12) 0.0417(13) 0.0042(10) 0.0109(11) 0.0033(10) C14 0.0640(17) 0.0549(15) 0.0566(17) 0.0127(13) 0.0104(13) 0.0228(13) C15 0.0457(14) 0.0761(18) 0.0543(17) 0.0038(14) 0.0051(12) 0.0221(14) C16 0.0367(12) 0.0651(16) 0.0462(14) -0.0034(12) 0.0115(11) 0.0002(11) C17 0.0354(11) 0.0402(11) 0.0300(11) -0.0043(8) 0.0119(9) 0.0021(9) C18 0.0303(10) 0.0372(11) 0.0392(12) -0.0048(9) 0.0133(9) -0.0037(8) C19 0.0488(13) 0.0441(12) 0.0430(13) -0.0128(10) 0.0167(11) -0.0030(10) C20 0.0543(15) 0.0400(13) 0.0701(19) -0.0198(12) 0.0235(13) -0.0031(11) C21 0.0516(14) 0.0313(11) 0.082(2) 0.0019(12) 0.0318(14) -0.0009(10) C22 0.0451(13) 0.0420(12) 0.0521(14) 0.0058(10) 0.0253(11) -0.0024(10) C23 0.0340(11) 0.0358(10) 0.0419(12) -0.0019(9) 0.0196(9) -0.0025(8) C24 0.0379(11) 0.0396(11) 0.0323(11) -0.0020(9) 0.0101(9) -0.0040(9) C25 0.0378(11) 0.0395(11) 0.0398(12) 0.0003(9) 0.0208(10) -0.0005(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9730(15) . ? Cu1 N1 1.9795(17) . ? Cu1 O4 2.0108(17) 7 ? Cu1 O3 2.0287(17) 7 ? Cu1 N3 2.1911(18) 5_565 ? Cu1 C25 2.362(2) 7 ? O1 C24 1.266(3) . ? N1 C1 1.338(3) . ? N1 N2 1.356(2) . ? C1 C2 1.404(3) . ? C1 C8 1.491(3) . ? N2 C3 1.351(3) . ? N2 H2A 0.8600 . ? C2 C3 1.374(3) . ? C2 C7 1.508(3) . ? O2 C24 1.230(3) . ? C3 C9 1.492(3) . ? N3 C4 1.338(3) . ? N3 N4 1.350(3) . ? N3 Cu1 2.1911(18) 5_565 ? O3 C25 1.258(3) . ? O3 Cu1 2.0287(17) 7 ? C4 C5 1.407(3) . ? C4 C10 1.497(3) . ? N4 C6 1.349(3) . ? N4 H4A 0.8600 . ? O4 C25 1.265(3) . ? O4 Cu1 2.0108(17) 7 ? C5 C6 1.374(3) . ? C5 C7 1.501(3) . ? C6 C11 1.497(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.397(3) . ? C12 C17 1.399(3) . ? C12 C24 1.506(3) . ? C13 C14 1.386(3) . ? C13 H13A 0.9300 . ? C14 C15 1.371(4) . ? C14 H14A 0.9300 . ? C15 C16 1.375(4) . ? C15 H15A 0.9300 . ? C16 C17 1.397(3) . ? C16 H16A 0.9300 . ? C17 C18 1.503(3) . ? C18 C19 1.387(3) . ? C18 C23 1.399(3) . ? C19 C20 1.387(3) . ? C19 H19A 0.9300 . ? C20 C21 1.376(4) . ? C20 H20A 0.9300 . ? C21 C22 1.378(4) . ? C21 H21A 0.9300 . ? C22 C23 1.397(3) . ? C22 H22A 0.9300 . ? C23 C25 1.482(3) . ? C25 Cu1 2.362(2) 7 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 90.47(7) . . ? O1 Cu1 O4 95.25(7) . 7 ? N1 Cu1 O4 162.74(7) . 7 ? O1 Cu1 O3 145.57(7) . 7 ? N1 Cu1 O3 102.17(7) . 7 ? O4 Cu1 O3 64.57(7) 7 7 ? O1 Cu1 N3 104.40(7) . 5_565 ? N1 Cu1 N3 97.29(7) . 5_565 ? O4 Cu1 N3 97.03(8) 7 5_565 ? O3 Cu1 N3 105.53(7) 7 5_565 ? O1 Cu1 C25 122.94(7) . 7 ? N1 Cu1 C25 133.50(7) . 7 ? O4 Cu1 C25 32.40(7) 7 7 ? O3 Cu1 C25 32.18(7) 7 7 ? N3 Cu1 C25 103.30(7) 5_565 7 ? C24 O1 Cu1 127.10(14) . . ? C1 N1 N2 105.61(17) . . ? C1 N1 Cu1 135.84(15) . . ? N2 N1 Cu1 117.26(13) . . ? N1 C1 C2 109.87(19) . . ? N1 C1 C8 122.5(2) . . ? C2 C1 C8 127.55(19) . . ? C3 N2 N1 111.96(17) . . ? C3 N2 H2A 124.0 . . ? N1 N2 H2A 124.0 . . ? C3 C2 C1 106.24(18) . . ? C3 C2 C7 127.4(2) . . ? C1 C2 C7 126.4(2) . . ? N2 C3 C2 106.30(19) . . ? N2 C3 C9 122.1(2) . . ? C2 C3 C9 131.6(2) . . ? C4 N3 N4 105.57(17) . . ? C4 N3 Cu1 135.85(16) . 5_565 ? N4 N3 Cu1 118.35(13) . 5_565 ? C25 O3 Cu1 88.65(13) . 7 ? N3 C4 C5 110.5(2) . . ? N3 C4 C10 121.4(2) . . ? C5 C4 C10 128.1(2) . . ? C6 N4 N3 111.70(18) . . ? C6 N4 H4A 124.2 . . ? N3 N4 H4A 124.2 . . ? C25 O4 Cu1 89.25(13) . 7 ? C6 C5 C4 105.03(19) . . ? C6 C5 C7 127.8(2) . . ? C4 C5 C7 127.1(2) . . ? N4 C6 C5 107.2(2) . . ? N4 C6 C11 121.6(2) . . ? C5 C6 C11 131.2(2) . . ? C5 C7 C2 113.55(17) . . ? C5 C7 H7A 108.9 . . ? C2 C7 H7A 108.9 . . ? C5 C7 H7B 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 119.3(2) . . ? C13 C12 C24 117.7(2) . . ? C17 C12 C24 122.95(18) . . ? C14 C13 C12 121.2(2) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C15 C14 C13 119.1(2) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C15 C16 C17 121.4(2) . . ? C15 C16 H16A 119.3 . . ? C17 C16 H16A 119.3 . . ? C16 C17 C12 118.3(2) . . ? C16 C17 C18 118.7(2) . . ? C12 C17 C18 122.58(18) . . ? C19 C18 C23 118.4(2) . . ? C19 C18 C17 116.35(19) . . ? C23 C18 C17 125.21(19) . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H19A 119.3 . . ? C18 C19 H19A 119.3 . . ? C21 C20 C19 120.3(2) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C22 119.0(2) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C21 C22 C23 121.5(2) . . ? C21 C22 H22A 119.3 . . ? C23 C22 H22A 119.3 . . ? C22 C23 C18 119.4(2) . . ? C22 C23 C25 118.3(2) . . ? C18 C23 C25 122.31(19) . . ? O2 C24 O1 124.3(2) . . ? O2 C24 C12 117.9(2) . . ? O1 C24 C12 117.71(19) . . ? O3 C25 O4 117.5(2) . . ? O3 C25 C23 122.2(2) . . ? O4 C25 C23 120.27(19) . . ? O3 C25 Cu1 59.18(11) . 7 ? O4 C25 Cu1 58.35(11) . 7 ? C23 C25 Cu1 177.68(15) . 7 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.84 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.325 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.057 # Attachment '- DPA_Ni.cif' data_11tb20 _database_code_depnum_ccdc_archive 'CCDC 838984' #TrackingRef '- DPA_Ni.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H50 N8 Ni O8' _chemical_formula_weight 949.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 19.5620(14) _cell_length_b 15.8621(12) _cell_length_c 15.3525(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4763.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11965 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 24.29 _exptl_crystal_description Cube _exptl_crystal_colour Green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 0.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.817933 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0817 before correction' _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 'Bruker APEX-2 CCD area detector' _diffrn_measurement_method '/w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28693 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 24.35 _reflns_number_total 3489 _reflns_number_gt 3302 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX-2' _computing_cell_refinement 'Bruker APEX-2' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0357P)^2^+4.6972P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.176(14) _refine_ls_number_reflns 3489 _refine_ls_number_parameters 311 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Ni1 Ni 0.5000 0.0000 0.24624(4) 0.02219(11) Uani 1 2 d S . . N1 N 0.50257(11) 0.09591(19) 0.34045(19) 0.0290(6) Uani 1 1 d . . . O1 O 0.39269(8) 0.00030(12) 0.23772(19) 0.0314(5) Uani 1 1 d . . . C1 C 0.54234(14) 0.16230(17) 0.3551(2) 0.0301(6) Uani 1 1 d . . . N2 N 0.46457(12) 0.08740(15) 0.41367(17) 0.0336(6) Uani 1 1 d . . . H2A H 0.4342 0.0488 0.4207 0.040 Uiso 1 1 calc R . . C2 C 0.53072(14) 0.19556(19) 0.4382(2) 0.0372(7) Uani 1 1 d . . . O2 O 0.35157(10) -0.00826(12) 0.37320(14) 0.0375(5) Uani 1 1 d . . . O3 O 0.16258(13) 0.02326(17) 0.53236(19) 0.0667(7) Uani 1 1 d . . . C3 C 0.47960(18) 0.1457(2) 0.4740(2) 0.0413(8) Uani 1 1 d . . . N3 N 0.49756(11) 0.40911(18) 0.64596(18) 0.0268(6) Uani 1 1 d . . . O4 O 0.24616(12) -0.04253(13) 0.46398(16) 0.0511(6) Uani 1 1 d . . . C4 C 0.54159(13) 0.34984(18) 0.6200(2) 0.0309(7) Uani 1 1 d . . . N4 N 0.45567(12) 0.42263(15) 0.57664(16) 0.0314(5) Uani 1 1 d . . . H4A H 0.4217 0.4571 0.5768 0.038 Uiso 1 1 calc R . . C5 C 0.52879(16) 0.32750(19) 0.5332(2) 0.0372(7) Uani 1 1 d . . . C6 C 0.47409(17) 0.3752(2) 0.5075(2) 0.0419(8) Uani 1 1 d . . . C7 C 0.56971(15) 0.2672(2) 0.4784(3) 0.0587(12) Uani 1 1 d . . . H7A H 0.5914 0.2990 0.4320 0.070 Uiso 1 1 calc R . . H7B H 0.6058 0.2438 0.5144 0.070 Uiso 1 1 calc R . . C8 C 0.59165(17) 0.1950(2) 0.2894(2) 0.0459(8) Uani 1 1 d . . . H8A H 0.5931 0.1573 0.2404 0.069 Uiso 1 1 calc R . . H8B H 0.6363 0.1988 0.3150 0.069 Uiso 1 1 calc R . . H8C H 0.5773 0.2498 0.2702 0.069 Uiso 1 1 calc R . . C9 C 0.4440(2) 0.1488(3) 0.5590(3) 0.0742(14) Uani 1 1 d . . . H9A H 0.4094 0.1058 0.5608 0.111 Uiso 1 1 calc R . . H9B H 0.4230 0.2031 0.5663 0.111 Uiso 1 1 calc R . . H9C H 0.4763 0.1395 0.6050 0.111 Uiso 1 1 calc R . . C10 C 0.59492(18) 0.3157(2) 0.6795(2) 0.0478(8) Uani 1 1 d . . . H10A H 0.5821 0.3265 0.7388 0.072 Uiso 1 1 calc R . . H10B H 0.6379 0.3426 0.6674 0.072 Uiso 1 1 calc R . . H10C H 0.5993 0.2561 0.6706 0.072 Uiso 1 1 calc R . . C11 C 0.4383(2) 0.3816(3) 0.4225(3) 0.0675(11) Uani 1 1 d . . . H11A H 0.4366 0.3271 0.3956 0.101 Uiso 1 1 calc R . . H11B H 0.4626 0.4200 0.3853 0.101 Uiso 1 1 calc R . . H11C H 0.3927 0.4021 0.4316 0.101 Uiso 1 1 calc R . . C12 C 0.34516(14) -0.00376(16) 0.2911(2) 0.0307(6) Uani 1 1 d . . . C13 C 0.27316(13) -0.00585(19) 0.2564(3) 0.0364(7) Uani 1 1 d . . . C14 C 0.25530(18) -0.0640(2) 0.1932(2) 0.0486(8) Uani 1 1 d . . . H14A H 0.2888 -0.0978 0.1683 0.058 Uiso 1 1 calc R . . C15 C 0.1883(2) -0.0722(3) 0.1668(3) 0.0632(10) Uani 1 1 d . . . H15A H 0.1767 -0.1117 0.1245 0.076 Uiso 1 1 calc R . . C16 C 0.13906(19) -0.0220(3) 0.2028(3) 0.0677(12) Uani 1 1 d . . . H16A H 0.0937 -0.0289 0.1862 0.081 Uiso 1 1 calc R . . C17 C 0.15582(16) 0.0385(3) 0.2635(3) 0.0587(10) Uani 1 1 d . . . H17A H 0.1221 0.0739 0.2856 0.070 Uiso 1 1 calc R . . C18 C 0.22326(15) 0.0472(2) 0.2920(2) 0.0408(7) Uani 1 1 d . . . C19 C 0.24043(14) 0.11602(19) 0.3549(2) 0.0408(7) Uani 1 1 d . . . C20 C 0.25977(15) 0.1953(2) 0.3230(3) 0.0514(8) Uani 1 1 d . . . H20A H 0.2627 0.2033 0.2631 0.062 Uiso 1 1 calc R . . C21 C 0.27443(18) 0.2608(2) 0.3771(3) 0.0627(10) Uani 1 1 d . . . H21A H 0.2878 0.3126 0.3544 0.075 Uiso 1 1 calc R . . C22 C 0.26935(18) 0.2499(2) 0.4658(3) 0.0670(13) Uani 1 1 d . . . H22A H 0.2797 0.2943 0.5030 0.080 Uiso 1 1 calc R . . C23 C 0.24902(19) 0.1735(2) 0.4996(3) 0.0574(8) Uani 1 1 d . . . H23A H 0.2449 0.1672 0.5596 0.069 Uiso 1 1 calc R . . C24 C 0.23466(14) 0.10622(19) 0.4454(2) 0.0438(8) Uani 1 1 d . . . C25 C 0.21106(16) 0.0253(2) 0.4843(2) 0.0472(8) Uani 1 1 d . . . H4 H 0.307(3) -0.022(4) 0.444(4) 0.13(2) 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 0.0296(2) 0.01963(19) 0.0174(2) 0.000 0.000 0.00098(18) N1 0.0360(15) 0.0285(14) 0.0227(15) -0.0025(12) 0.0036(10) -0.0015(9) O1 0.0298(8) 0.0331(8) 0.0314(14) 0.0005(8) 0.0017(11) -0.0009(8) C1 0.0330(14) 0.0256(14) 0.0317(17) -0.0077(12) 0.0010(11) 0.0026(12) N2 0.0378(12) 0.0330(13) 0.0302(15) -0.0055(11) 0.0076(11) -0.0046(10) C2 0.0329(14) 0.0416(17) 0.0372(18) -0.0157(14) 0.0008(13) 0.0000(13) O2 0.0369(10) 0.0442(11) 0.0316(12) -0.0010(9) 0.0019(8) 0.0027(8) O3 0.0555(15) 0.0791(17) 0.0653(18) 0.0041(15) 0.0308(13) -0.0068(13) C3 0.0442(16) 0.050(2) 0.0297(18) -0.0165(16) 0.0055(14) 0.0009(15) N3 0.0359(15) 0.0235(13) 0.0211(16) -0.0031(11) -0.0013(9) 0.0031(9) O4 0.0617(14) 0.0385(12) 0.0531(15) 0.0032(11) 0.0184(13) -0.0060(11) C4 0.0318(14) 0.0270(14) 0.0338(18) -0.0088(13) 0.0034(12) -0.0009(11) N4 0.0393(12) 0.0348(13) 0.0200(13) -0.0036(11) -0.0064(10) 0.0020(10) C5 0.0355(15) 0.0383(16) 0.0379(19) -0.0182(15) 0.0027(14) -0.0080(13) C6 0.0416(17) 0.0532(19) 0.0310(18) -0.0131(15) -0.0030(14) -0.0135(15) C7 0.0413(15) 0.069(3) 0.066(3) -0.044(2) 0.0125(16) -0.0124(16) C8 0.0543(19) 0.0383(17) 0.045(2) -0.0099(15) 0.0106(15) -0.0148(14) C9 0.081(3) 0.090(3) 0.051(3) -0.028(2) 0.029(2) -0.026(2) C10 0.0544(19) 0.0412(18) 0.048(2) -0.0094(15) -0.0043(16) 0.0179(15) C11 0.073(2) 0.097(3) 0.032(2) -0.018(2) -0.0150(17) -0.003(2) C12 0.0341(14) 0.0241(13) 0.0340(16) -0.0005(12) 0.0000(12) 0.0004(11) C13 0.0326(12) 0.0387(13) 0.038(2) 0.0051(14) 0.0018(15) -0.0041(12) C14 0.0502(19) 0.059(2) 0.0363(19) -0.0015(17) -0.0005(15) -0.0084(17) C15 0.060(2) 0.075(3) 0.054(2) 0.000(2) -0.0111(18) -0.022(2) C16 0.0385(19) 0.096(3) 0.068(3) 0.006(2) -0.0106(18) -0.012(2) C17 0.0306(15) 0.072(2) 0.073(3) 0.011(2) -0.0030(17) 0.0051(16) C18 0.0396(16) 0.0437(16) 0.0389(18) 0.0079(15) 0.0044(14) 0.0014(14) C19 0.0315(14) 0.0383(16) 0.053(2) 0.0031(15) 0.0062(13) 0.0084(12) C20 0.0413(17) 0.0469(18) 0.066(2) 0.0126(18) 0.0085(16) 0.0068(14) C21 0.052(2) 0.041(2) 0.095(3) 0.008(2) 0.005(2) -0.0001(15) C22 0.059(2) 0.0414(19) 0.101(4) -0.020(2) 0.004(2) -0.0015(16) C23 0.0536(17) 0.059(2) 0.059(2) -0.015(2) 0.0093(15) 0.0011(19) C24 0.0361(16) 0.0394(16) 0.056(2) -0.0024(15) 0.0127(14) 0.0033(13) C25 0.0448(17) 0.0545(19) 0.042(2) -0.0009(17) 0.0080(15) -0.0090(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 Ni1 N1 2.100(3) . ? Ni1 N1 2.100(3) 2_655 ? Ni1 O1 2.1034(15) . ? Ni1 O1 2.1034(16) 2_655 ? Ni1 N3 2.110(3) 5_544 ? Ni1 N3 2.110(3) 6_654 ? N1 C1 1.328(4) . ? N1 N2 1.354(4) . ? O1 C12 1.241(4) . ? C1 C2 1.399(4) . ? C1 C8 1.489(4) . ? N2 C3 1.342(4) . ? N2 H2A 0.8600 . ? C2 C3 1.388(5) . ? C2 C7 1.502(4) . ? O2 C12 1.269(4) . ? O2 H4 1.41(6) . ? O3 C25 1.202(4) . ? C3 C9 1.481(5) . ? N3 C4 1.336(4) . ? N3 N4 1.360(4) . ? N3 Ni1 2.110(3) 5 ? O4 C25 1.314(4) . ? O4 H4 1.27(6) . ? C4 C5 1.403(4) . ? C4 C10 1.488(4) . ? N4 C6 1.351(4) . ? N4 H4A 0.8600 . ? C5 C6 1.368(5) . ? C5 C7 1.504(5) . ? C6 C11 1.483(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.506(4) . ? C13 C14 1.384(5) . ? C13 C18 1.400(4) . ? C14 C15 1.378(5) . ? C14 H14A 0.9300 . ? C15 C16 1.367(6) . ? C15 H15A 0.9300 . ? C16 C17 1.378(6) . ? C16 H16A 0.9300 . ? C17 C18 1.397(4) . ? C17 H17A 0.9300 . ? C18 C19 1.496(5) . ? C19 C20 1.401(4) . ? C19 C24 1.402(5) . ? C20 C21 1.362(6) . ? C20 H20A 0.9300 . ? C21 C22 1.375(6) . ? C21 H21A 0.9300 . ? C22 C23 1.377(5) . ? C22 H22A 0.9300 . ? C23 C24 1.383(5) . ? C23 H23A 0.9300 . ? C24 C25 1.489(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N1 92.92(16) . 2_655 ? N1 Ni1 O1 93.73(9) . . ? N1 Ni1 O1 91.18(9) 2_655 . ? N1 Ni1 O1 91.18(9) . 2_655 ? N1 Ni1 O1 93.73(9) 2_655 2_655 ? O1 Ni1 O1 172.87(16) . 2_655 ? N1 Ni1 N3 176.67(14) . 5_544 ? N1 Ni1 N3 90.40(8) 2_655 5_544 ? O1 Ni1 N3 86.19(9) . 5_544 ? O1 Ni1 N3 88.60(9) 2_655 5_544 ? N1 Ni1 N3 90.40(8) . 6_654 ? N1 Ni1 N3 176.67(14) 2_655 6_654 ? O1 Ni1 N3 88.60(9) . 6_654 ? O1 Ni1 N3 86.19(9) 2_655 6_654 ? N3 Ni1 N3 86.27(15) 5_544 6_654 ? C1 N1 N2 105.1(3) . . ? C1 N1 Ni1 134.8(2) . . ? N2 N1 Ni1 119.1(2) . . ? C12 O1 Ni1 135.0(2) . . ? N1 C1 C2 111.0(3) . . ? N1 C1 C8 122.8(3) . . ? C2 C1 C8 126.3(3) . . ? C3 N2 N1 112.6(3) . . ? C3 N2 H2A 123.7 . . ? N1 N2 H2A 123.7 . . ? C3 C2 C1 105.3(3) . . ? C3 C2 C7 129.3(3) . . ? C1 C2 C7 125.3(3) . . ? C12 O2 H4 136(2) . . ? N2 C3 C2 106.1(3) . . ? N2 C3 C9 121.9(3) . . ? C2 C3 C9 132.1(3) . . ? C4 N3 N4 105.5(3) . . ? C4 N3 Ni1 133.1(2) . 5 ? N4 N3 Ni1 118.48(19) . 5 ? C25 O4 H4 110(2) . . ? N3 C4 C5 110.2(3) . . ? N3 C4 C10 121.7(3) . . ? C5 C4 C10 128.0(3) . . ? C6 N4 N3 111.5(3) . . ? C6 N4 H4A 124.2 . . ? N3 N4 H4A 124.2 . . ? C6 C5 C4 105.9(3) . . ? C6 C5 C7 127.3(3) . . ? C4 C5 C7 126.7(3) . . ? N4 C6 C5 106.8(3) . . ? N4 C6 C11 121.8(3) . . ? C5 C6 C11 131.3(3) . . ? C2 C7 C5 116.2(2) . . ? C2 C7 H7A 108.2 . . ? C5 C7 H7A 108.2 . . ? C2 C7 H7B 108.2 . . ? C5 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C6 C11 H11A 109.5 . . ? C6 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C6 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 O2 125.8(3) . . ? O1 C12 C13 118.0(3) . . ? O2 C12 C13 116.2(3) . . ? C14 C13 C18 119.9(3) . . ? C14 C13 C12 119.9(3) . . ? C18 C13 C12 120.1(3) . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C16 C15 C14 119.7(4) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C18 C13 118.5(3) . . ? C17 C18 C19 119.1(3) . . ? C13 C18 C19 122.3(3) . . ? C20 C19 C24 117.9(3) . . ? C20 C19 C18 119.3(3) . . ? C24 C19 C18 122.7(3) . . ? C21 C20 C19 121.8(4) . . ? C21 C20 H20A 119.1 . . ? C19 C20 H20A 119.1 . . ? C20 C21 C22 119.5(4) . . ? C20 C21 H21A 120.2 . . ? C22 C21 H21A 120.2 . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C22 C23 C24 120.7(4) . . ? C22 C23 H23A 119.6 . . ? C24 C23 H23A 119.6 . . ? C23 C24 C19 119.6(3) . . ? C23 C24 C25 119.2(3) . . ? C19 C24 C25 121.1(3) . . ? O3 C25 O4 122.4(3) . . ? O3 C25 C24 120.9(3) . . ? O4 C25 C24 116.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.147 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.039