Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'Christer Aakeroy' 'Alicia M. Beatty' 'John Desper' M.O'Shea 'Jesus Valdes-Martinez' _publ_contact_author_name 'Dr Christer Aakeroy' _publ_contact_author_address ; Department of Chemistry Kansas State University Manhattan Kansas 66506 UNITED STATES OF AMERICA ; _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Directed assembly of dinuclear and mononuclear copper(II)-carboxylates into infinite 1-D motifs using isonicotinamide as a high-yielding supramolecular reagent ; data_1 _database_code_CSD 215919 _audit_creation_method SHELXL-97 _chemical_name_systematic ; copper(II)(isonicotinamide)diacetate ; _chemical_name_common copper(ii)(isonicotinamide)diacetate _chemical_melting_point ? _chemical_formula_moiety ; (C10 H12 Cu1 N2 O5) (C2 H3 N) ; _chemical_formula_sum 'C12 H15 Cu N3 O5' _chemical_formula_weight 344.81 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 7.1996(10) _cell_length_b 8.1027(12) _cell_length_c 13.4485(19) _cell_angle_alpha 90.408(2) _cell_angle_beta 96.328(3) _cell_angle_gamma 96.118(2) _cell_volume 775.17(19) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 886 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.1 _exptl_crystal_description prism _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 1.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.701 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Gottingen, Germany, 2001 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5410 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 28.21 _reflns_number_total 3443 _reflns_number_gt 3026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0511P)^2^+0.0993P] 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 3443 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.87812(3) 0.92716(3) 0.429986(17) 0.02361(9) Uani 1 1 d . . . C1S C 0.8172(3) 0.0429(3) 0.09491(16) 0.0691(9) Uani 1 1 d . . . H1S H 0.8770 0.0479 0.1633 0.083 Uiso 1 1 calc R . . H2S H 0.9069 0.0874 0.0506 0.083 Uiso 1 1 calc R . . H3S H 0.7739 -0.0716 0.0759 0.083 Uiso 1 1 calc R . . C2S C 0.6594(3) 0.1393(3) 0.08747(16) 0.0518(6) Uani 1 1 d R . . N1S N 0.5354(4) 0.2127(3) 0.07612(19) 0.0602(6) Uani 1 1 d . . . N1 N 0.6624(2) 0.8062(2) 0.31900(13) 0.0279(4) Uani 1 1 d . . . C2 C 0.6958(3) 0.6940(3) 0.25243(17) 0.0354(5) Uani 1 1 d . . . H2 H 0.8185 0.6637 0.2538 0.042 Uiso 1 1 calc R . . C3 C 0.5578(3) 0.6198(3) 0.18116(17) 0.0350(5) Uani 1 1 d . . . H3 H 0.5860 0.5401 0.1356 0.042 Uiso 1 1 calc R . . C4 C 0.3769(3) 0.6660(3) 0.17851(14) 0.0275(4) Uani 1 1 d . . . C5 C 0.3425(3) 0.7818(3) 0.24744(17) 0.0378(5) Uani 1 1 d . . . H5 H 0.2217 0.8161 0.2472 0.045 Uiso 1 1 calc R . . C6 C 0.4878(3) 0.8474(3) 0.31715(17) 0.0384(5) Uani 1 1 d . . . H6 H 0.4622 0.9242 0.3652 0.046 Uiso 1 1 calc R . . O7 O 0.0759(2) 0.6719(2) 0.08791(13) 0.0451(4) Uani 1 1 d . . . N7 N 0.2351(3) 0.4557(3) 0.05487(15) 0.0369(5) Uani 1 1 d . . . H7B H 0.149(4) 0.411(3) 0.013(2) 0.044 Uiso 1 1 d . . . H7A H 0.324(4) 0.406(3) 0.066(2) 0.044 Uiso 1 1 d . . . C7 C 0.2169(3) 0.5962(3) 0.10257(15) 0.0316(5) Uani 1 1 d . . . C21 C 1.1779(3) 1.1411(3) 0.36499(16) 0.0327(5) Uani 1 1 d . . . O1 O 1.0349(2) 1.0423(2) 0.33457(11) 0.0408(4) Uani 1 1 d . . . O2 O 1.2411(2) 1.1675(2) 0.45470(11) 0.0364(4) Uani 1 1 d . . . C22 C 1.2798(4) 1.2343(4) 0.2874(2) 0.0557(7) Uani 1 1 d . . . H22C H 1.2602 1.1707 0.2250 0.083 Uiso 1 1 calc R . . H22B H 1.4131 1.2514 0.3102 0.083 Uiso 1 1 calc R . . H22A H 1.2318 1.3409 0.2769 0.083 Uiso 1 1 calc R . . C31 C 1.1849(3) 0.7511(3) 0.49988(17) 0.0301(4) Uani 1 1 d . . . O3 O 1.0407(2) 0.74733(19) 0.43740(12) 0.0359(4) Uani 1 1 d . . . O4 O 1.2454(2) 0.87020(19) 0.55918(12) 0.0387(4) Uani 1 1 d . . . C32 C 1.2907(3) 0.6009(3) 0.5050(2) 0.0488(7) Uani 1 1 d . . . H32C H 1.2715 0.5437 0.4405 0.073 Uiso 1 1 calc R . . H32B H 1.2454 0.5269 0.5555 0.073 Uiso 1 1 calc R . . H32A H 1.4237 0.6351 0.5223 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01988(13) 0.02367(14) 0.02596(14) -0.00406(9) -0.00223(9) 0.00149(9) C1S 0.068(2) 0.073(2) 0.070(2) 0.0178(17) 0.0070(16) 0.0233(17) C2S 0.0556(16) 0.0527(16) 0.0481(15) 0.0088(13) 0.0101(12) 0.0060(13) N1S 0.0669(16) 0.0591(15) 0.0583(15) -0.0025(12) 0.0097(12) 0.0208(13) N1 0.0213(8) 0.0305(9) 0.0308(9) -0.0053(7) -0.0016(6) 0.0033(6) C2 0.0234(9) 0.0414(13) 0.0402(12) -0.0120(10) -0.0020(8) 0.0048(8) C3 0.0296(10) 0.0401(13) 0.0343(12) -0.0140(9) -0.0005(8) 0.0041(9) C4 0.0257(9) 0.0320(11) 0.0226(10) -0.0039(8) -0.0027(7) -0.0007(8) C5 0.0216(10) 0.0489(14) 0.0410(13) -0.0160(10) -0.0047(9) 0.0054(9) C6 0.0274(10) 0.0462(14) 0.0398(13) -0.0203(10) -0.0033(9) 0.0043(9) O7 0.0331(8) 0.0517(11) 0.0463(10) -0.0176(8) -0.0161(7) 0.0074(7) N7 0.0335(10) 0.0379(11) 0.0351(10) -0.0105(8) -0.0109(8) 0.0001(8) C7 0.0281(10) 0.0375(12) 0.0264(10) -0.0048(9) -0.0037(8) -0.0023(8) C21 0.0338(10) 0.0306(11) 0.0344(11) -0.0008(9) 0.0081(9) 0.0029(8) O1 0.0428(9) 0.0489(10) 0.0276(8) -0.0007(7) 0.0033(6) -0.0090(7) O2 0.0321(8) 0.0416(9) 0.0337(8) -0.0011(7) 0.0056(6) -0.0063(6) C22 0.0627(17) 0.0593(18) 0.0429(15) 0.0047(13) 0.0168(12) -0.0147(14) C31 0.0243(9) 0.0246(10) 0.0417(12) -0.0021(9) 0.0040(8) 0.0036(7) O3 0.0281(7) 0.0316(8) 0.0470(9) -0.0120(7) -0.0044(6) 0.0090(6) O4 0.0333(8) 0.0300(8) 0.0508(10) -0.0085(7) -0.0110(7) 0.0105(6) C32 0.0389(13) 0.0309(12) 0.0764(19) -0.0091(12) -0.0039(12) 0.0139(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9605(14) . ? Cu1 O4 1.9609(15) 2_776 ? Cu1 O2 1.9749(15) 2_776 ? Cu1 O1 1.9758(16) . ? Cu1 N1 2.1783(16) . ? Cu1 Cu1 2.6111(5) 2_776 ? C1S C2S 1.4409 . ? C2S N1S 1.122(3) . ? N1 C2 1.330(3) . ? N1 C6 1.332(3) . ? C2 C3 1.386(3) . ? C3 C4 1.390(3) . ? C4 C5 1.375(3) . ? C4 C7 1.511(2) . ? C5 C6 1.383(3) . ? O7 C7 1.239(3) . ? N7 C7 1.328(3) . ? C21 O2 1.250(3) . ? C21 O1 1.262(3) . ? C21 C22 1.504(3) . ? O2 Cu1 1.9750(15) 2_776 ? C31 O4 1.257(2) . ? C31 O3 1.259(2) . ? C31 C32 1.501(3) . ? O4 Cu1 1.9609(15) 2_776 ? 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 168.80(6) . 2_776 ? O3 Cu1 O2 89.17(7) . 2_776 ? O4 Cu1 O2 90.65(7) 2_776 2_776 ? O3 Cu1 O1 89.53(7) . . ? O4 Cu1 O1 88.49(8) 2_776 . ? O2 Cu1 O1 168.90(6) 2_776 . ? O3 Cu1 N1 96.23(6) . . ? O4 Cu1 N1 94.95(6) 2_776 . ? O2 Cu1 N1 94.25(6) 2_776 . ? O1 Cu1 N1 96.85(6) . . ? O3 Cu1 Cu1 85.47(4) . 2_776 ? O4 Cu1 Cu1 83.39(4) 2_776 2_776 ? O2 Cu1 Cu1 82.92(5) 2_776 2_776 ? O1 Cu1 Cu1 85.98(5) . 2_776 ? N1 Cu1 Cu1 176.69(5) . 2_776 ? N1S C2S C1S 176.15(18) . . ? C2 N1 C6 118.15(17) . . ? C2 N1 Cu1 123.48(13) . . ? C6 N1 Cu1 118.37(14) . . ? N1 C2 C3 122.91(19) . . ? C2 C3 C4 118.6(2) . . ? C5 C4 C3 118.45(17) . . ? C5 C4 C7 118.51(18) . . ? C3 C4 C7 123.03(19) . . ? C4 C5 C6 119.19(19) . . ? N1 C6 C5 122.7(2) . . ? O7 C7 N7 123.33(18) . . ? O7 C7 C4 118.82(19) . . ? N7 C7 C4 117.86(19) . . ? O2 C21 O1 125.1(2) . . ? O2 C21 C22 117.5(2) . . ? O1 C21 C22 117.5(2) . . ? C21 O1 Cu1 120.98(14) . . ? C21 O2 Cu1 124.90(14) . 2_776 ? O4 C31 O3 124.95(19) . . ? O4 C31 C32 117.55(18) . . ? O3 C31 C32 117.50(19) . . ? C31 O3 Cu1 121.80(14) . . ? C31 O4 Cu1 124.29(13) . 2_776 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Cu1 N1 C2 -26.87(19) . . . . ? O4 Cu1 N1 C2 152.48(19) 2_776 . . . ? O2 Cu1 N1 C2 -116.49(19) 2_776 . . . ? O1 Cu1 N1 C2 63.41(19) . . . . ? Cu1 Cu1 N1 C2 -147.8(7) 2_776 . . . ? O3 Cu1 N1 C6 153.58(18) . . . . ? O4 Cu1 N1 C6 -27.07(19) 2_776 . . . ? O2 Cu1 N1 C6 63.96(18) 2_776 . . . ? O1 Cu1 N1 C6 -116.14(18) . . . . ? Cu1 Cu1 N1 C6 32.7(9) 2_776 . . . ? C6 N1 C2 C3 0.6(4) . . . . ? Cu1 N1 C2 C3 -178.98(18) . . . . ? N1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C3 C4 C7 178.5(2) . . . . ? C3 C4 C5 C6 -0.4(4) . . . . ? C7 C4 C5 C6 -179.7(2) . . . . ? C2 N1 C6 C5 -1.8(4) . . . . ? Cu1 N1 C6 C5 177.8(2) . . . . ? C4 C5 C6 N1 1.8(4) . . . . ? C5 C4 C7 O7 17.7(3) . . . . ? C3 C4 C7 O7 -161.5(2) . . . . ? C5 C4 C7 N7 -162.2(2) . . . . ? C3 C4 C7 N7 18.6(3) . . . . ? O2 C21 O1 Cu1 4.9(3) . . . . ? C22 C21 O1 Cu1 -174.98(18) . . . . ? O3 Cu1 O1 C21 -88.13(18) . . . . ? O4 Cu1 O1 C21 80.85(18) 2_776 . . . ? O2 Cu1 O1 C21 -4.8(4) 2_776 . . . ? N1 Cu1 O1 C21 175.65(17) . . . . ? Cu1 Cu1 O1 C21 -2.63(17) 2_776 . . . ? O1 C21 O2 Cu1 -4.5(3) . . . 2_776 ? C22 C21 O2 Cu1 175.40(17) . . . 2_776 ? O4 C31 O3 Cu1 -3.9(3) . . . . ? C32 C31 O3 Cu1 175.08(17) . . . . ? O4 Cu1 O3 C31 9.1(5) 2_776 . . . ? O2 Cu1 O3 C31 -80.09(18) 2_776 . . . ? O1 Cu1 O3 C31 88.88(18) . . . . ? N1 Cu1 O3 C31 -174.28(17) . . . . ? Cu1 Cu1 O3 C31 2.88(17) 2_776 . . . ? O3 C31 O4 Cu1 2.3(3) . . . 2_776 ? C32 C31 O4 Cu1 -176.69(17) . . . 2_776 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A N1S 0.79(3) 2.29(3) 3.069(3) 166(3) . N7 H7B O7 0.84(3) 2.05(3) 2.881(2) 173(3) 2_565 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 28.21 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.781 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.063 #===END data_2 _database_code_CSD 215920 _audit_creation_method SHELXL-97 _chemical_name_systematic ; copper(II)bis(isonicotinamide)bis(2-fluorobenzoate) ; _chemical_name_common copper(ii)bis(isonicotinamide)bis(2-fluorobenzoate) _chemical_melting_point ? _chemical_formula_moiety ; C26 H24 Cu F2 N4 O8 ; _chemical_formula_sum 'C26 H24 Cu F2 N4 O8' _chemical_formula_weight 622.03 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' F F 0.0171 0.0103 '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 7.4814(12) _cell_length_b 7.7279(14) _cell_length_c 12.586(2) _cell_angle_alpha 72.762(3) _cell_angle_beta 72.803(3) _cell_angle_gamma 77.970(3) _cell_volume 658.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 716 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 25.3 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 319 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Gottingen, Germany, 2001 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4651 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2958 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0400P)^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 2958 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.03132(16) Uani 1 2 d S . . O1S O 0.7555(3) 0.5469(3) 0.59342(18) 0.0454(5) Uani 1 1 d . . . H1S H 0.807(4) 0.465(4) 0.559(3) 0.054 Uiso 1 1 d . . . H2S H 0.853(4) 0.615(4) 0.574(2) 0.054 Uiso 1 1 d . . . N1 N 0.5069(3) 0.7406(3) 0.37556(17) 0.0277(5) Uani 1 1 d . . . C2 C 0.4664(4) 0.8992(3) 0.4046(2) 0.0331(6) Uani 1 1 d . . . H2 H 0.4378 0.8958 0.4831 0.040 Uiso 1 1 calc R . . C3 C 0.4636(4) 1.0668(3) 0.3276(2) 0.0338(6) Uani 1 1 d . . . H3 H 0.4364 1.1743 0.3531 0.041 Uiso 1 1 calc R . . C4 C 0.5013(3) 1.0760(3) 0.2119(2) 0.0274(5) Uani 1 1 d . . . C5 C 0.5447(3) 0.9113(3) 0.1808(2) 0.0327(6) Uani 1 1 d . . . H5 H 0.5727 0.9108 0.1030 0.039 Uiso 1 1 calc R . . C6 C 0.5467(3) 0.7497(3) 0.2633(2) 0.0312(6) Uani 1 1 d . . . H6 H 0.5774 0.6400 0.2401 0.037 Uiso 1 1 calc R . . O7 O 0.5585(3) 1.2518(2) 0.01925(15) 0.0446(5) Uani 1 1 d . . . N7 N 0.4275(4) 1.4045(3) 0.1560(2) 0.0427(7) Uani 1 1 d . . . H7A H 0.392(4) 1.409(4) 0.224(3) 0.051 Uiso 1 1 d . . . H7B H 0.437(4) 1.489(4) 0.113(3) 0.051 Uiso 1 1 d . . . C7 C 0.4982(3) 1.2534(3) 0.1209(2) 0.0313(6) Uani 1 1 d . . . C11 C 0.9248(3) 0.2032(3) 0.2946(2) 0.0313(6) Uani 1 1 d . . . F12 F 0.8999(3) 0.4679(2) 0.14724(15) 0.0751(6) Uani 1 1 d . . . C12 C 0.9492(4) 0.2849(4) 0.1796(2) 0.0439(7) Uani 1 1 d . . . C13 C 1.0253(4) 0.1919(4) 0.0964(3) 0.0552(8) Uani 1 1 d . . . H13 H 1.0427 0.2540 0.0183 0.066 Uiso 1 1 calc R . . C14 C 1.0760(4) 0.0068(4) 0.1281(3) 0.0519(8) Uani 1 1 d . . . H14 H 1.1272 -0.0598 0.0720 0.062 Uiso 1 1 calc R . . C15 C 1.0514(4) -0.0807(4) 0.2427(3) 0.0481(8) Uani 1 1 d . . . H15 H 1.0843 -0.2080 0.2649 0.058 Uiso 1 1 calc R . . C16 C 0.9795(3) 0.0160(4) 0.3248(2) 0.0401(7) Uani 1 1 d . . . H16 H 0.9671 -0.0454 0.4027 0.048 Uiso 1 1 calc R . . O17 O 0.6680(2) 0.3826(2) 0.38486(14) 0.0322(4) Uani 1 1 d . . . C17 C 0.8341(3) 0.3050(3) 0.3854(2) 0.0306(6) Uani 1 1 d . . . O18 O 0.9189(2) 0.2986(3) 0.45810(16) 0.0426(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 0.0454(3) 0.0169(2) 0.0230(3) -0.00080(18) -0.0017(2) -0.00169(19) O1S 0.0377(11) 0.0462(13) 0.0510(14) -0.0183(11) -0.0025(10) -0.0068(9) N1 0.0371(11) 0.0190(10) 0.0232(11) -0.0024(9) -0.0052(9) -0.0037(9) C2 0.0553(15) 0.0222(13) 0.0210(13) -0.0038(11) -0.0080(12) -0.0081(12) C3 0.0545(16) 0.0186(12) 0.0278(14) -0.0047(11) -0.0096(13) -0.0063(11) C4 0.0352(12) 0.0211(12) 0.0231(13) -0.0035(10) -0.0051(11) -0.0041(10) C5 0.0503(15) 0.0244(13) 0.0178(13) -0.0045(11) -0.0044(12) -0.0004(11) C6 0.0435(14) 0.0214(13) 0.0258(14) -0.0074(11) -0.0053(12) -0.0005(11) O7 0.0796(13) 0.0231(10) 0.0214(10) -0.0014(8) -0.0063(10) -0.0009(9) N7 0.0763(17) 0.0180(12) 0.0225(13) 0.0000(10) -0.0046(13) -0.0010(12) C7 0.0453(14) 0.0206(13) 0.0242(14) -0.0017(11) -0.0084(12) -0.0021(11) C11 0.0313(12) 0.0291(14) 0.0303(14) -0.0091(12) -0.0036(11) -0.0009(11) F12 0.1182(16) 0.0332(10) 0.0406(11) 0.0009(9) 0.0078(11) 0.0065(10) C12 0.0528(17) 0.0318(16) 0.0362(17) -0.0085(14) 0.0004(14) 0.0008(13) C13 0.069(2) 0.053(2) 0.0297(16) -0.0097(15) -0.0004(15) 0.0023(16) C14 0.0579(18) 0.053(2) 0.0448(19) -0.0303(17) -0.0075(15) 0.0097(15) C15 0.0550(17) 0.0338(16) 0.054(2) -0.0211(15) -0.0150(16) 0.0135(14) C16 0.0473(15) 0.0327(15) 0.0373(16) -0.0096(13) -0.0123(13) 0.0046(12) O17 0.0409(9) 0.0211(9) 0.0256(10) -0.0024(8) -0.0027(8) 0.0021(7) C17 0.0398(14) 0.0189(12) 0.0282(14) -0.0020(11) -0.0042(12) -0.0055(11) O18 0.0468(10) 0.0447(12) 0.0415(12) -0.0184(10) -0.0098(10) -0.0078(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 O17 1.9312(16) . ? Cu1 O17 1.9312(16) 2_666 ? Cu1 N1 2.0444(19) 2_666 ? Cu1 N1 2.0445(19) . ? N1 C2 1.331(3) . ? N1 C6 1.339(3) . ? C2 C3 1.369(3) . ? C3 C4 1.382(3) . ? C4 C5 1.388(3) . ? C4 C7 1.504(3) . ? C5 C6 1.368(3) . ? O7 C7 1.228(3) . ? N7 C7 1.323(3) . ? C11 C12 1.370(4) . ? C11 C16 1.387(3) . ? C11 C17 1.497(3) . ? F12 C12 1.353(3) . ? C12 C13 1.364(4) . ? C13 C14 1.369(4) . ? C14 C15 1.374(4) . ? C15 C16 1.370(4) . ? O17 C17 1.263(3) . ? C17 O18 1.243(3) . ? 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 O17 Cu1 O17 180.00(8) . 2_666 ? O17 Cu1 N1 92.08(7) . 2_666 ? O17 Cu1 N1 87.91(7) 2_666 2_666 ? O17 Cu1 N1 87.91(7) . . ? O17 Cu1 N1 92.09(7) 2_666 . ? N1 Cu1 N1 180.0 2_666 . ? C2 N1 C6 116.5(2) . . ? C2 N1 Cu1 120.08(17) . . ? C6 N1 Cu1 123.35(16) . . ? N1 C2 C3 124.2(2) . . ? C2 C3 C4 119.2(2) . . ? C3 C4 C5 116.9(2) . . ? C3 C4 C7 123.2(2) . . ? C5 C4 C7 119.9(2) . . ? C6 C5 C4 120.1(2) . . ? N1 C6 C5 123.0(2) . . ? O7 C7 N7 123.4(2) . . ? O7 C7 C4 119.4(2) . . ? N7 C7 C4 117.2(2) . . ? C12 C11 C16 116.7(2) . . ? C12 C11 C17 122.9(2) . . ? C16 C11 C17 120.3(2) . . ? F12 C12 C13 118.6(3) . . ? F12 C12 C11 118.1(2) . . ? C13 C12 C11 123.3(3) . . ? C12 C13 C14 119.1(3) . . ? C13 C14 C15 119.4(3) . . ? C16 C15 C14 120.6(3) . . ? C15 C16 C11 120.9(3) . . ? C17 O17 Cu1 125.86(17) . . ? O18 C17 O17 125.3(2) . . ? O18 C17 C11 119.5(2) . . ? O17 C17 C11 115.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O17 Cu1 N1 C2 -157.26(19) . . . . ? O17 Cu1 N1 C2 22.74(19) 2_666 . . . ? N1 Cu1 N1 C2 -87(66) 2_666 . . . ? O17 Cu1 N1 C6 24.36(19) . . . . ? O17 Cu1 N1 C6 -155.64(19) 2_666 . . . ? N1 Cu1 N1 C6 94(66) 2_666 . . . ? C6 N1 C2 C3 -0.1(4) . . . . ? Cu1 N1 C2 C3 -178.60(19) . . . . ? N1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C2 C3 C4 C7 178.9(2) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? C7 C4 C5 C6 -179.7(2) . . . . ? C2 N1 C6 C5 -0.8(4) . . . . ? Cu1 N1 C6 C5 177.67(18) . . . . ? C4 C5 C6 N1 0.5(4) . . . . ? C3 C4 C7 O7 169.9(2) . . . . ? C5 C4 C7 O7 -9.7(4) . . . . ? C3 C4 C7 N7 -10.9(4) . . . . ? C5 C4 C7 N7 169.6(3) . . . . ? C16 C11 C12 F12 -179.0(2) . . . . ? C17 C11 C12 F12 4.4(4) . . . . ? C16 C11 C12 C13 -0.9(4) . . . . ? C17 C11 C12 C13 -177.5(3) . . . . ? F12 C12 C13 C14 179.8(3) . . . . ? C11 C12 C13 C14 1.8(5) . . . . ? C12 C13 C14 C15 -0.8(5) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? C14 C15 C16 C11 1.9(4) . . . . ? C12 C11 C16 C15 -1.0(4) . . . . ? C17 C11 C16 C15 175.7(2) . . . . ? O17 Cu1 O17 C17 -46(100) 2_666 . . . ? N1 Cu1 O17 C17 -63.45(19) 2_666 . . . ? N1 Cu1 O17 C17 116.55(19) . . . . ? Cu1 O17 C17 O18 -3.2(3) . . . . ? Cu1 O17 C17 C11 172.19(15) . . . . ? C12 C11 C17 O18 -126.0(3) . . . . ? C16 C11 C17 O18 57.4(3) . . . . ? C12 C11 C17 O17 58.3(3) . . . . ? C16 C11 C17 O17 -118.2(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1S H1S O18 0.83(3) 1.97(3) 2.794(3) 171(3) . O1S H2S O18 0.92(3) 1.85(3) 2.757(3) 167(3) 2_766 N7 H7A O1S 0.83(3) 2.33(3) 3.145(3) 170(3) 2_676 N7 H7B O7 0.71(3) 2.19(3) 2.905(3) 175(3) 2_685 _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.344 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.066 #===END data_3 _database_code_CSD 215921 _audit_creation_method SHELXL-97 _chemical_name_systematic ; copper(II)(isonicotinamide)diacetate ; _chemical_name_common copper(ii)(isonicotinamide)diacetate _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cu N4 O6,C1 H4 O,(C1 H4 O)0.25' _chemical_formula_sum 'C17.25 H23 Cu N4 O7.25' _chemical_formula_weight 465.94 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 9.3053(17) _cell_length_b 10.1542(19) _cell_length_c 12.885(2) _cell_angle_alpha 69.735(3) _cell_angle_beta 75.696(3) _cell_angle_gamma 67.129(3) _cell_volume 1043.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 979 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.0 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 483 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Gottingen, Germany, 2001 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7222 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4620 _reflns_number_gt 3820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0650P)^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 4620 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.53959(3) 0.56425(3) 0.595484(19) 0.02338(11) Uani 1 1 d . . . N1 N 0.6508(2) 0.6929(2) 0.47258(14) 0.0246(4) Uani 1 1 d . . . O1S O 0.4459(3) 0.8205(2) 0.91321(17) 0.0550(6) Uani 1 1 d . . . H1S H 0.4935 0.7936 0.8565 0.066 Uiso 1 1 calc R . . C1S C 0.3804(5) 0.7118(3) 0.9880(3) 0.0635(10) Uani 1 1 d . . . H1SA H 0.3353 0.6773 0.9464 0.095 Uiso 1 1 calc R . . H1SB H 0.2990 0.7553 1.0417 0.095 Uiso 1 1 calc R . . H1SC H 0.4623 0.6285 1.0268 0.095 Uiso 1 1 calc R . . C2S C 0.797(2) 0.877(2) 0.6425(15) 0.087(5) Uiso 0.25 1 d P . . H2SA H 0.8235 0.7698 0.6721 0.131 Uiso 0.25 1 calc PR . . H2SB H 0.8926 0.9013 0.6100 0.131 Uiso 0.25 1 calc PR . . H2SC H 0.7284 0.9136 0.5857 0.131 Uiso 0.25 1 calc PR . . O2S O 0.7282(16) 0.9369(15) 0.7200(11) 0.101(4) Uiso 0.25 1 d P . . H2S H 0.6402 0.9964 0.7046 0.121 Uiso 0.25 1 calc PR . . C2 C 0.7966(3) 0.6288(3) 0.42572(19) 0.0299(5) Uani 1 1 d . . . H2 H 0.8417 0.5245 0.4491 0.036 Uiso 1 1 calc R . . C3 C 0.8826(3) 0.7086(3) 0.34551(19) 0.0303(5) Uani 1 1 d . . . H3 H 0.9834 0.6593 0.3139 0.036 Uiso 1 1 calc R . . C4 C 0.8194(3) 0.8627(3) 0.31144(17) 0.0251(5) Uani 1 1 d . . . C5 C 0.6691(3) 0.9304(3) 0.35914(18) 0.0281(5) Uani 1 1 d . . . H5 H 0.6226 1.0346 0.3380 0.034 Uiso 1 1 calc R . . C6 C 0.5887(3) 0.8423(3) 0.43801(18) 0.0282(5) Uani 1 1 d . . . H6 H 0.4862 0.8888 0.4689 0.034 Uiso 1 1 calc R . . O7 O 1.0191(2) 0.8867(2) 0.15933(16) 0.0486(5) Uani 1 1 d . . . C7 C 0.9177(3) 0.9480(3) 0.22480(18) 0.0300(5) Uani 1 1 d . . . N7 N 0.8886(3) 1.0854(3) 0.22547(19) 0.0421(6) Uani 1 1 d . . . H7A H 0.939(4) 1.142(4) 0.180(3) 0.050 Uiso 1 1 d . . . H7B H 0.828(4) 1.117(3) 0.280(3) 0.050 Uiso 1 1 d . . . N21 N 0.4278(2) 0.4443(2) 0.72652(14) 0.0257(4) Uani 1 1 d . . . C22 C 0.2955(3) 0.5099(3) 0.78559(19) 0.0329(5) Uani 1 1 d . . . H22 H 0.2549 0.6145 0.7657 0.039 Uiso 1 1 calc R . . C23 C 0.2160(3) 0.4314(3) 0.87415(19) 0.0308(5) Uani 1 1 d . . . H23 H 0.1238 0.4819 0.9139 0.037 Uiso 1 1 calc R . . C24 C 0.2737(3) 0.2764(3) 0.90416(17) 0.0259(5) Uani 1 1 d . . . C25 C 0.4119(3) 0.2078(3) 0.84446(18) 0.0307(5) Uani 1 1 d . . . H25 H 0.4550 0.1034 0.8628 0.037 Uiso 1 1 calc R . . C26 C 0.4856(3) 0.2946(3) 0.75766(18) 0.0305(5) Uani 1 1 d . . . H26 H 0.5804 0.2470 0.7186 0.037 Uiso 1 1 calc R . . O27 O 0.0691(2) 0.2607(2) 1.05578(16) 0.0473(5) Uani 1 1 d . . . C27 C 0.1815(3) 0.1924(3) 0.99837(19) 0.0322(5) Uani 1 1 d . . . N27 N 0.2266(3) 0.0472(3) 1.0150(2) 0.0416(6) Uani 1 1 d . . . H27A H 0.174(4) 0.001(4) 1.057(3) 0.050 Uiso 1 1 d . . . H27B H 0.285(4) 0.006(4) 0.968(3) 0.050 Uiso 1 1 d . . . O31 O 0.36829(18) 0.62515(17) 0.50434(12) 0.0263(3) Uani 1 1 d . . . C31 C 0.2576(3) 0.7443(3) 0.51719(18) 0.0293(5) Uani 1 1 d . . . O32 O 0.2604(2) 0.8116(2) 0.57972(14) 0.0380(4) Uani 1 1 d . . . C32 C 0.1226(4) 0.8016(4) 0.4520(3) 0.0656(10) Uani 1 1 d . . . H32A H 0.0471 0.8917 0.4689 0.098 Uiso 1 1 calc R . . H32B H 0.0724 0.7270 0.4719 0.098 Uiso 1 1 calc R . . H32C H 0.1609 0.8235 0.3728 0.098 Uiso 1 1 calc R . . O41 O 0.7143(2) 0.49748(19) 0.68134(13) 0.0320(4) Uani 1 1 d . . . C41 C 0.6838(3) 0.5854(3) 0.7405(2) 0.0395(6) Uani 1 1 d . . . O42 O 0.5613(2) 0.6946(2) 0.73859(16) 0.0496(5) Uani 1 1 d . . . C42 C 0.8054(4) 0.5503(5) 0.8137(3) 0.0738(12) Uani 1 1 d . . . H42A H 0.7704 0.6239 0.8546 0.111 Uiso 1 1 calc R . . H42B H 0.9046 0.5524 0.7676 0.111 Uiso 1 1 calc R . . H42C H 0.8192 0.4522 0.8659 0.111 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02600(17) 0.02449(17) 0.01987(14) -0.00360(10) 0.00096(10) -0.01331(12) N1 0.0272(10) 0.0249(10) 0.0226(8) -0.0058(7) 0.0021(7) -0.0135(8) O1S 0.0710(15) 0.0437(12) 0.0474(11) -0.0244(10) 0.0074(10) -0.0151(11) C1S 0.093(3) 0.0384(18) 0.0554(18) -0.0170(15) -0.0038(18) -0.0183(18) C2 0.0277(12) 0.0236(12) 0.0361(12) -0.0068(9) 0.0009(10) -0.0107(10) C3 0.0264(12) 0.0290(13) 0.0342(11) -0.0105(10) 0.0045(10) -0.0114(10) C4 0.0272(12) 0.0295(12) 0.0227(10) -0.0090(9) 0.0029(9) -0.0159(10) C5 0.0303(13) 0.0244(12) 0.0288(10) -0.0077(9) 0.0015(9) -0.0111(10) C6 0.0277(12) 0.0259(12) 0.0295(11) -0.0085(9) 0.0044(9) -0.0115(10) O7 0.0543(13) 0.0366(11) 0.0484(11) -0.0171(9) 0.0269(10) -0.0242(10) C7 0.0349(13) 0.0319(13) 0.0235(10) -0.0056(9) 0.0043(9) -0.0182(11) N7 0.0541(16) 0.0332(13) 0.0380(11) -0.0144(10) 0.0227(11) -0.0272(12) N21 0.0306(10) 0.0263(10) 0.0189(8) -0.0050(7) 0.0027(7) -0.0130(8) C22 0.0383(14) 0.0241(12) 0.0298(11) -0.0056(9) 0.0046(10) -0.0109(11) C23 0.0328(13) 0.0243(12) 0.0298(11) -0.0088(9) 0.0070(10) -0.0095(10) C24 0.0316(12) 0.0271(12) 0.0205(9) -0.0057(9) 0.0010(9) -0.0147(10) C25 0.0340(13) 0.0222(12) 0.0285(11) -0.0042(9) 0.0028(10) -0.0082(10) C26 0.0319(13) 0.0293(13) 0.0244(10) -0.0061(9) 0.0045(9) -0.0102(10) O27 0.0563(13) 0.0315(10) 0.0458(10) -0.0153(8) 0.0272(9) -0.0225(9) C27 0.0374(14) 0.0309(13) 0.0264(10) -0.0065(10) 0.0069(10) -0.0175(11) N27 0.0469(15) 0.0295(12) 0.0402(12) -0.0096(10) 0.0200(11) -0.0199(11) O31 0.0277(9) 0.0269(9) 0.0250(7) -0.0070(6) -0.0016(6) -0.0113(7) C31 0.0291(12) 0.0316(13) 0.0278(10) -0.0080(9) 0.0009(9) -0.0139(11) O32 0.0419(11) 0.0419(11) 0.0355(9) -0.0194(8) 0.0033(8) -0.0172(9) C32 0.049(2) 0.060(2) 0.091(3) -0.0361(19) -0.0365(19) 0.0079(17) O41 0.0316(9) 0.0388(10) 0.0272(8) -0.0120(7) -0.0033(7) -0.0113(8) C41 0.0363(15) 0.0531(17) 0.0342(12) -0.0209(12) -0.0044(11) -0.0127(13) O42 0.0456(12) 0.0538(13) 0.0519(11) -0.0296(10) -0.0120(9) -0.0028(10) C42 0.059(2) 0.106(3) 0.072(2) -0.055(2) -0.0266(19) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O41 1.9591(17) . ? Cu1 O31 1.9895(16) . ? Cu1 N1 2.0227(18) . ? Cu1 N21 2.0270(18) . ? N1 C2 1.346(3) . ? N1 C6 1.347(3) . ? O1S C1S 1.419(4) . ? C2S O2S 1.256(19) . ? C2 C3 1.371(3) . ? C3 C4 1.387(3) . ? C4 C5 1.388(3) . ? C4 C7 1.508(3) . ? C5 C6 1.380(3) . ? O7 C7 1.226(3) . ? C7 N7 1.316(3) . ? N21 C22 1.338(3) . ? N21 C26 1.345(3) . ? C22 C23 1.377(3) . ? C23 C24 1.392(3) . ? C24 C25 1.384(3) . ? C24 C27 1.508(3) . ? C25 C26 1.381(3) . ? O27 C27 1.238(3) . ? C27 N27 1.320(3) . ? O31 C31 1.280(3) . ? C31 O32 1.234(3) . ? C31 C32 1.495(4) . ? O41 C41 1.275(3) . ? C41 O42 1.242(3) . ? C41 C42 1.509(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 O41 Cu1 O31 177.31(6) . . ? O41 Cu1 N1 88.33(7) . . ? O31 Cu1 N1 91.27(7) . . ? O41 Cu1 N21 89.46(7) . . ? O31 Cu1 N21 91.12(7) . . ? N1 Cu1 N21 175.58(7) . . ? C2 N1 C6 117.48(18) . . ? C2 N1 Cu1 119.39(15) . . ? C6 N1 Cu1 123.05(15) . . ? N1 C2 C3 123.0(2) . . ? C2 C3 C4 119.4(2) . . ? C3 C4 C5 118.2(2) . . ? C3 C4 C7 118.3(2) . . ? C5 C4 C7 123.5(2) . . ? C6 C5 C4 119.0(2) . . ? N1 C6 C5 122.9(2) . . ? O7 C7 N7 124.1(2) . . ? O7 C7 C4 119.1(2) . . ? N7 C7 C4 116.8(2) . . ? C22 N21 C26 117.52(19) . . ? C22 N21 Cu1 121.77(16) . . ? C26 N21 Cu1 120.70(15) . . ? N21 C22 C23 123.1(2) . . ? C22 C23 C24 119.2(2) . . ? C25 C24 C23 118.0(2) . . ? C25 C24 C27 123.5(2) . . ? C23 C24 C27 118.5(2) . . ? C26 C25 C24 119.2(2) . . ? N21 C26 C25 122.9(2) . . ? O27 C27 N27 123.2(2) . . ? O27 C27 C24 119.6(2) . . ? N27 C27 C24 117.1(2) . . ? C31 O31 Cu1 112.53(14) . . ? O32 C31 O31 122.3(2) . . ? O32 C31 C32 120.3(2) . . ? O31 C31 C32 117.4(2) . . ? C41 O41 Cu1 108.84(16) . . ? O42 C41 O41 122.5(2) . . ? O42 C41 C42 121.1(2) . . ? O41 C41 C42 116.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O41 Cu1 N1 C2 58.66(17) . . . . ? O31 Cu1 N1 C2 -118.68(17) . . . . ? N21 Cu1 N1 C2 118.6(9) . . . . ? O41 Cu1 N1 C6 -118.13(18) . . . . ? O31 Cu1 N1 C6 64.52(18) . . . . ? N21 Cu1 N1 C6 -58.2(10) . . . . ? C6 N1 C2 C3 -0.1(3) . . . . ? Cu1 N1 C2 C3 -177.06(18) . . . . ? N1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -1.1(3) . . . . ? C2 C3 C4 C7 178.8(2) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C7 C4 C5 C6 -179.9(2) . . . . ? C2 N1 C6 C5 -1.1(3) . . . . ? Cu1 N1 C6 C5 175.73(17) . . . . ? C4 C5 C6 N1 1.2(4) . . . . ? C3 C4 C7 O7 25.9(3) . . . . ? C5 C4 C7 O7 -154.2(2) . . . . ? C3 C4 C7 N7 -153.6(2) . . . . ? C5 C4 C7 N7 26.2(3) . . . . ? O41 Cu1 N21 C22 111.96(19) . . . . ? O31 Cu1 N21 C22 -70.66(19) . . . . ? N1 Cu1 N21 C22 52.1(10) . . . . ? O41 Cu1 N21 C26 -67.53(18) . . . . ? O31 Cu1 N21 C26 109.85(18) . . . . ? N1 Cu1 N21 C26 -127.4(9) . . . . ? C26 N21 C22 C23 -1.3(4) . . . . ? Cu1 N21 C22 C23 179.24(19) . . . . ? N21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C25 1.5(4) . . . . ? C22 C23 C24 C27 -177.6(2) . . . . ? C23 C24 C25 C26 -0.6(4) . . . . ? C27 C24 C25 C26 178.3(2) . . . . ? C22 N21 C26 C25 2.2(4) . . . . ? Cu1 N21 C26 C25 -178.33(18) . . . . ? C24 C25 C26 N21 -1.2(4) . . . . ? C25 C24 C27 O27 172.0(2) . . . . ? C23 C24 C27 O27 -9.1(4) . . . . ? C25 C24 C27 N27 -8.1(4) . . . . ? C23 C24 C27 N27 170.9(2) . . . . ? O41 Cu1 O31 C31 -169.0(13) . . . . ? N1 Cu1 O31 C31 -87.74(15) . . . . ? N21 Cu1 O31 C31 88.54(15) . . . . ? Cu1 O31 C31 O32 0.1(3) . . . . ? Cu1 O31 C31 C32 179.5(2) . . . . ? O31 Cu1 O41 C41 170.9(12) . . . . ? N1 Cu1 O41 C41 89.59(18) . . . . ? N21 Cu1 O41 C41 -86.58(18) . . . . ? Cu1 O41 C41 O42 -0.7(3) . . . . ? Cu1 O41 C41 C42 179.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N7 H7A O27 0.86(3) 2.08(3) 2.930(3) 172(3) 1_664 N7 H7B O32 0.86(3) 2.04(3) 2.879(3) 165(3) 2_676 N27 H27A O7 0.79(3) 2.11(3) 2.901(3) 174(3) 1_446 N27 H27B O1S 0.83(3) 2.11(3) 2.881(3) 154(3) 1_545 O1S H1S O42 0.83 1.95 2.754(3) 162.2 . _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 0.577 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.075 #===END data_4 _database_code_CSD 215922 _audit_creation_method SHELXL-97 _chemical_name_systematic ; copper(II)bis(isonicotinamide)diacetate diacetic acid ; _chemical_name_common 'copper(ii)bis(isonicotinamide)diacetate diacetic acid' _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cu N4 O6,(C2 H4 O2)2' _chemical_formula_sum 'C20 H26 Cu N4 O10' _chemical_formula_weight 545.99 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0398(15) _cell_length_b 15.245(2) _cell_length_c 15.650(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.910(3) _cell_angle_gamma 90.00 _cell_volume 2545.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 1015 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 26.9 _exptl_crystal_description prism _exptl_crystal_colour blue_green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 0.916 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.47 _exptl_absorpt_correction_T_max 0.71 _exptl_absorpt_process_details ; Sheldrick, G.M. SADABS. Version 2. Multi-Scan Absorption Correction Program. University of Gottingen, Germany, 2001 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17266 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5872 _reflns_number_gt 4263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0600P)^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 5872 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.40546(2) 0.814956(17) 0.601436(16) 0.02731(10) Uani 1 1 d . . . N11 N 0.28027(16) 0.81469(11) 0.48406(11) 0.0269(4) Uani 1 1 d . . . C12 C 0.1570(2) 0.80622(16) 0.47654(15) 0.0359(5) Uani 1 1 d . . . H12 H 0.1290 0.8004 0.5281 0.043 Uiso 1 1 calc R . . C13 C 0.0699(2) 0.80571(16) 0.39556(14) 0.0358(5) Uani 1 1 d . . . H13 H -0.0159 0.8001 0.3926 0.043 Uiso 1 1 calc R . . C14 C 0.10904(19) 0.81347(14) 0.31894(14) 0.0272(4) Uani 1 1 d . . . C15 C 0.23678(19) 0.82246(15) 0.32703(14) 0.0316(5) Uani 1 1 d . . . H15 H 0.2671 0.8282 0.2764 0.038 Uiso 1 1 calc R . . C16 C 0.3180(2) 0.82284(14) 0.40974(14) 0.0307(5) Uani 1 1 d . . . H16 H 0.4042 0.8291 0.4144 0.037 Uiso 1 1 calc R . . C17 C 0.0120(2) 0.81218(15) 0.23114(14) 0.0315(5) Uani 1 1 d . . . N17 N 0.05322(19) 0.81699(16) 0.15886(13) 0.0439(6) Uani 1 1 d . . . H17A H -0.002(3) 0.8150(16) 0.108(2) 0.053 Uiso 1 1 d . . . H17B H 0.133(3) 0.8247(16) 0.1588(18) 0.053 Uiso 1 1 d . . . O17 O -0.10026(14) 0.80663(12) 0.22906(10) 0.0422(4) Uani 1 1 d . . . N21 N 0.51302(16) 0.81028(11) 0.72647(11) 0.0273(4) Uani 1 1 d . . . C22 C 0.6355(2) 0.79137(15) 0.74273(14) 0.0319(5) Uani 1 1 d . . . H22 H 0.6685 0.7768 0.6949 0.038 Uiso 1 1 calc R . . C23 C 0.7148(2) 0.79237(15) 0.82631(14) 0.0318(5) Uani 1 1 d . . . H23 H 0.8006 0.7806 0.8347 0.038 Uiso 1 1 calc R . . C24 C 0.66717(19) 0.81094(13) 0.89831(13) 0.0268(4) Uani 1 1 d . . . C25 C 0.5403(2) 0.82810(14) 0.88186(14) 0.0287(5) Uani 1 1 d . . . H25 H 0.5043 0.8399 0.9289 0.034 Uiso 1 1 calc R . . C26 C 0.4670(2) 0.82783(14) 0.79598(14) 0.0296(5) Uani 1 1 d . . . H26 H 0.3811 0.8405 0.7857 0.035 Uiso 1 1 calc R . . C27 C 0.7585(2) 0.81243(15) 0.98818(14) 0.0324(5) Uani 1 1 d . . . N27 N 0.71498(19) 0.82901(15) 1.05786(13) 0.0352(5) Uani 1 1 d . . . H27A H 0.760(3) 0.8272(17) 1.1024(19) 0.042 Uiso 1 1 d . . . H27B H 0.637(3) 0.8332(16) 1.0501(17) 0.042 Uiso 1 1 d . . . O27 O 0.87003(15) 0.80097(14) 0.99310(11) 0.0544(5) Uani 1 1 d . . . C31 C 0.2865(3) 0.96258(19) 0.64839(16) 0.0473(7) Uani 1 1 d . . . O31 O 0.37895(15) 0.94153(11) 0.61714(10) 0.0408(4) Uani 1 1 d . . . O32 O 0.20952(18) 0.90785(14) 0.65951(12) 0.0564(5) Uani 1 1 d . . . C32 C 0.2785(4) 1.0581(2) 0.6711(2) 0.0866(12) Uani 1 1 d . . . H32A H 0.2041 1.0678 0.6918 0.130 Uiso 1 1 calc R . . H32B H 0.2741 1.0935 0.6189 0.130 Uiso 1 1 calc R . . H32C H 0.3522 1.0743 0.7171 0.130 Uiso 1 1 calc R . . C41 C 0.38891(19) 0.64306(16) 0.60627(13) 0.0306(5) Uani 1 1 d . . . O41 O 0.46247(13) 0.69560(9) 0.57992(9) 0.0286(3) Uani 1 1 d . . . O42 O 0.30293(15) 0.67118(11) 0.63606(11) 0.0400(4) Uani 1 1 d . . . C42 C 0.4109(3) 0.54753(17) 0.59960(18) 0.0501(7) Uani 1 1 d . . . H42A H 0.5003 0.5359 0.6167 0.075 Uiso 1 1 calc R . . H42B H 0.3762 0.5284 0.5392 0.075 Uiso 1 1 calc R . . H42C H 0.3707 0.5159 0.6386 0.075 Uiso 1 1 calc R . . C51 C 0.6521(2) 0.92749(19) 0.58220(18) 0.0494(7) Uani 1 1 d . . . O51 O 0.61062(19) 0.99042(13) 0.62564(15) 0.0673(6) Uani 1 1 d . . . H51 H 0.5380 0.9789 0.6278 0.081 Uiso 1 1 calc R . . O52 O 0.58557(16) 0.86845(12) 0.54491(11) 0.0461(4) Uani 1 1 d . . . C52 C 0.7878(3) 0.9356(2) 0.5859(2) 0.0702(9) Uani 1 1 d . . . H52A H 0.8086 0.8957 0.5435 0.105 Uiso 1 1 calc R . . H52B H 0.8374 0.9210 0.6449 0.105 Uiso 1 1 calc R . . H52C H 0.8060 0.9953 0.5718 0.105 Uiso 1 1 calc R . . C61 C 0.1451(3) 0.9324(2) 0.8559(2) 0.0581(8) Uani 1 1 d . . . O61 O 0.07314(13) 0.92979(11) 0.77459(9) 0.0763(7) Uani 1 1 d . A . H61 H 0.1176 0.9273 0.7392 0.092 Uiso 1 1 calc R . . O62 O 0.25603(13) 0.92399(11) 0.87315(9) 0.0861(8) Uani 1 1 d R A . C62A C 0.07264(13) 0.94844(11) 0.92342(9) 0.0740(10) Uani 0.73(2) 1 d PR A 1 H62A H -0.0161 0.9517 0.8942 0.111 Uiso 0.73(2) 1 calc PR A 1 H62B H 0.0997 1.0033 0.9538 0.111 Uiso 0.73(2) 1 calc PR A 1 H62F H 0.0875 0.9008 0.9659 0.111 Uiso 0.73(2) 1 calc PR A 1 C62B C 0.07264(13) 0.94844(11) 0.92342(9) 0.0740(10) Uani 0.27(2) 1 d P A 2 H62D H 0.0058 0.9900 0.9001 0.111 Uiso 0.27(2) 1 calc PR A 2 H62E H 0.1283 0.9721 0.9768 0.111 Uiso 0.27(2) 1 calc PR A 2 H62F' H 0.0370 0.8936 0.9370 0.111 Uiso 0.27(2) 1 calc PR A 2 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 0.02573(15) 0.03518(16) 0.01730(14) -0.00152(11) -0.00122(10) 0.00242(11) N11 0.0257(9) 0.0339(10) 0.0190(8) -0.0002(7) 0.0020(7) 0.0007(7) C12 0.0278(11) 0.0572(15) 0.0216(11) 0.0014(10) 0.0047(9) -0.0018(10) C13 0.0226(10) 0.0596(16) 0.0246(11) 0.0000(11) 0.0049(9) -0.0045(10) C14 0.0229(10) 0.0367(12) 0.0198(10) 0.0002(9) 0.0012(8) 0.0002(9) C15 0.0257(10) 0.0486(14) 0.0202(10) 0.0012(10) 0.0053(8) 0.0004(9) C16 0.0228(10) 0.0426(13) 0.0251(11) -0.0019(10) 0.0033(8) 0.0006(9) C17 0.0246(10) 0.0469(13) 0.0205(10) -0.0008(10) 0.0013(8) -0.0007(9) N17 0.0204(9) 0.0915(18) 0.0177(9) -0.0007(10) 0.0012(8) -0.0006(10) O17 0.0218(8) 0.0810(13) 0.0215(8) 0.0012(8) 0.0017(6) -0.0026(7) N21 0.0263(9) 0.0330(10) 0.0192(8) -0.0012(7) 0.0001(7) 0.0022(7) C22 0.0302(11) 0.0436(13) 0.0210(10) -0.0013(9) 0.0047(9) 0.0086(9) C23 0.0260(11) 0.0441(13) 0.0236(11) -0.0005(9) 0.0031(9) 0.0071(9) C24 0.0260(10) 0.0327(11) 0.0193(10) -0.0012(9) 0.0017(8) -0.0007(8) C25 0.0272(10) 0.0373(12) 0.0219(10) -0.0016(9) 0.0068(8) -0.0010(9) C26 0.0234(10) 0.0392(13) 0.0242(11) 0.0006(9) 0.0029(8) 0.0020(9) C27 0.0252(10) 0.0487(14) 0.0215(10) 0.0009(10) 0.0027(8) -0.0022(10) N27 0.0229(9) 0.0612(14) 0.0190(9) -0.0014(9) 0.0012(7) -0.0027(9) O27 0.0224(8) 0.1163(17) 0.0217(8) -0.0060(9) 0.0008(7) 0.0044(9) C31 0.0564(17) 0.0528(16) 0.0262(12) -0.0025(12) -0.0010(12) 0.0222(14) O31 0.0432(9) 0.0379(9) 0.0354(9) -0.0030(7) -0.0004(7) 0.0085(8) O32 0.0513(11) 0.0794(15) 0.0379(10) -0.0095(10) 0.0106(9) 0.0095(10) C32 0.125(3) 0.058(2) 0.077(3) -0.0105(18) 0.026(2) 0.034(2) C41 0.0272(11) 0.0412(13) 0.0212(10) 0.0007(9) 0.0024(9) -0.0004(9) O41 0.0238(7) 0.0379(9) 0.0249(8) -0.0010(6) 0.0077(6) 0.0007(6) O42 0.0342(9) 0.0559(11) 0.0332(9) 0.0018(8) 0.0149(7) 0.0019(7) C42 0.0571(16) 0.0389(14) 0.0570(17) 0.0020(13) 0.0198(14) -0.0007(12) C51 0.0455(15) 0.0505(16) 0.0445(15) 0.0141(13) -0.0026(12) -0.0062(13) O51 0.0575(13) 0.0515(12) 0.0875(16) -0.0134(12) 0.0089(11) -0.0168(10) O52 0.0414(10) 0.0492(11) 0.0424(10) 0.0005(8) 0.0014(8) -0.0086(8) C52 0.0476(17) 0.077(2) 0.080(2) 0.0047(19) 0.0063(16) -0.0161(16) C61 0.0586(18) 0.0619(19) 0.0600(19) -0.0086(16) 0.0268(16) 0.0037(15) O61 0.0484(12) 0.125(2) 0.0569(13) -0.0084(14) 0.0165(10) 0.0130(12) O62 0.0546(13) 0.146(2) 0.0568(14) -0.0234(15) 0.0137(11) 0.0174(14) C62A 0.078(2) 0.087(3) 0.071(2) -0.0041(19) 0.0440(19) 0.0038(19) C62B 0.078(2) 0.087(3) 0.071(2) -0.0041(19) 0.0440(19) 0.0038(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O31 1.9765(16) . ? Cu1 O41 1.9824(14) . ? Cu1 N11 1.9944(17) . ? Cu1 N21 2.0121(18) . ? N11 C16 1.339(3) . ? N11 C12 1.342(3) . ? C12 C13 1.380(3) . ? C13 C14 1.380(3) . ? C14 C15 1.390(3) . ? C14 C17 1.509(3) . ? C15 C16 1.372(3) . ? C17 O17 1.234(3) . ? C17 N17 1.325(3) . ? N21 C26 1.341(3) . ? N21 C22 1.341(3) . ? C22 C23 1.374(3) . ? C23 C24 1.390(3) . ? C24 C25 1.382(3) . ? C24 C27 1.505(3) . ? C25 C26 1.379(3) . ? C27 O27 1.226(3) . ? C27 N27 1.324(3) . ? C31 O32 1.235(3) . ? C31 O31 1.281(3) . ? C31 C32 1.506(4) . ? C41 O42 1.237(2) . ? C41 O41 1.282(3) . ? C41 C42 1.485(3) . ? C51 O52 1.212(3) . ? C51 O51 1.324(3) . ? C51 C52 1.490(4) . ? C61 O62 1.191(3) . ? C61 O61 1.316(3) . ? C61 C62A 1.500(3) . ? 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 O31 Cu1 O41 168.79(6) . . ? O31 Cu1 N11 91.54(7) . . ? O41 Cu1 N11 90.96(7) . . ? O31 Cu1 N21 89.02(7) . . ? O41 Cu1 N21 89.94(6) . . ? N11 Cu1 N21 172.45(7) . . ? C16 N11 C12 117.93(18) . . ? C16 N11 Cu1 120.21(14) . . ? C12 N11 Cu1 121.86(14) . . ? N11 C12 C13 122.19(19) . . ? C12 C13 C14 119.8(2) . . ? C13 C14 C15 117.82(19) . . ? C13 C14 C17 118.82(18) . . ? C15 C14 C17 123.36(18) . . ? C16 C15 C14 119.22(19) . . ? N11 C16 C15 123.03(19) . . ? O17 C17 N17 123.0(2) . . ? O17 C17 C14 119.83(18) . . ? N17 C17 C14 117.21(19) . . ? C26 N21 C22 117.58(18) . . ? C26 N21 Cu1 122.00(14) . . ? C22 N21 Cu1 120.39(14) . . ? N21 C22 C23 122.84(19) . . ? C22 C23 C24 119.54(19) . . ? C25 C24 C23 117.64(19) . . ? C25 C24 C27 125.06(18) . . ? C23 C24 C27 117.29(18) . . ? C26 C25 C24 119.58(19) . . ? N21 C26 C25 122.77(19) . . ? O27 C27 N27 123.1(2) . . ? O27 C27 C24 118.50(18) . . ? N27 C27 C24 118.32(19) . . ? O32 C31 O31 122.0(2) . . ? O32 C31 C32 122.4(3) . . ? O31 C31 C32 115.6(3) . . ? C31 O31 Cu1 116.74(18) . . ? O42 C41 O41 121.1(2) . . ? O42 C41 C42 121.5(2) . . ? O41 C41 C42 117.49(19) . . ? C41 O41 Cu1 105.29(13) . . ? O52 C51 O51 122.6(2) . . ? O52 C51 C52 124.0(3) . . ? O51 C51 C52 113.4(3) . . ? O62 C61 O61 123.1(2) . . ? O62 C61 C62A 124.1(3) . . ? O61 C61 C62A 112.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O31 Cu1 N11 C16 96.18(16) . . . . ? O41 Cu1 N11 C16 -72.89(16) . . . . ? N21 Cu1 N11 C16 -169.7(5) . . . . ? O31 Cu1 N11 C12 -84.01(18) . . . . ? O41 Cu1 N11 C12 106.92(17) . . . . ? N21 Cu1 N11 C12 10.1(6) . . . . ? C16 N11 C12 C13 0.0(3) . . . . ? Cu1 N11 C12 C13 -179.80(18) . . . . ? N11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C12 C13 C14 C17 179.6(2) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C17 C14 C15 C16 -179.9(2) . . . . ? C12 N11 C16 C15 -0.3(3) . . . . ? Cu1 N11 C16 C15 179.49(17) . . . . ? C14 C15 C16 N11 0.2(3) . . . . ? C13 C14 C17 O17 1.9(3) . . . . ? C15 C14 C17 O17 -177.8(2) . . . . ? C13 C14 C17 N17 -177.9(2) . . . . ? C15 C14 C17 N17 2.3(3) . . . . ? O31 Cu1 N21 C26 62.94(17) . . . . ? O41 Cu1 N21 C26 -128.22(16) . . . . ? N11 Cu1 N21 C26 -31.4(6) . . . . ? O31 Cu1 N21 C22 -115.35(17) . . . . ? O41 Cu1 N21 C22 53.49(17) . . . . ? N11 Cu1 N21 C22 150.3(5) . . . . ? C26 N21 C22 C23 -2.3(3) . . . . ? Cu1 N21 C22 C23 176.04(17) . . . . ? N21 C22 C23 C24 2.1(4) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? C22 C23 C24 C27 -179.1(2) . . . . ? C23 C24 C25 C26 -1.2(3) . . . . ? C27 C24 C25 C26 177.6(2) . . . . ? C22 N21 C26 C25 0.8(3) . . . . ? Cu1 N21 C26 C25 -177.54(16) . . . . ? C24 C25 C26 N21 0.9(3) . . . . ? C25 C24 C27 O27 -175.8(2) . . . . ? C23 C24 C27 O27 3.0(3) . . . . ? C25 C24 C27 N27 2.0(3) . . . . ? C23 C24 C27 N27 -179.3(2) . . . . ? O32 C31 O31 Cu1 -7.5(3) . . . . ? C32 C31 O31 Cu1 172.16(19) . . . . ? O41 Cu1 O31 C31 -173.1(3) . . . . ? N11 Cu1 O31 C31 84.12(17) . . . . ? N21 Cu1 O31 C31 -88.35(17) . . . . ? O42 C41 O41 Cu1 1.1(2) . . . . ? C42 C41 O41 Cu1 -178.95(17) . . . . ? O31 Cu1 O41 C41 170.4(3) . . . . ? N11 Cu1 O41 C41 -86.69(13) . . . . ? N21 Cu1 O41 C41 85.81(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N17 H17A O27 0.87(3) 1.99(3) 2.860(3) 176(2) 1_454 N17 H17B O42 0.89(3) 2.00(3) 2.875(2) 169(3) 4_575 N27 H27A O17 0.74(3) 2.20(3) 2.940(3) 173(3) 1_656 N27 H27B O41 0.84(3) 2.14(3) 2.920(2) 154(2) 4_576 O61 H61 O32 0.83 1.82 2.649(2) 173.0 . O51 H51 O31 0.83 1.81 2.634(3) 170.4 . _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.506 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.059 #===END data_5 _database_code_CSD 215923 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(isonicotinamide)-bis(2-fluorobenzoate)(2-fluorobenzoic acid)copper(II) ; _chemical_name_common ;bis(isonicotinamide)-bis(2-fluorobenzoate)(2-fluorobenzoic acid)copper(ii) ; _chemical_melting_point ? _chemical_formula_moiety ; (C6 H6 N2 O)2 (C7 H4 O2 F)2 (C7 H5 O2 F) Cu ; _chemical_formula_sum 'C33 H25 Cu F3 N4 O8' _chemical_formula_weight 726.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0792(14) _cell_length_b 19.771(2) _cell_length_c 15.5280(19) _cell_angle_alpha 90.00 _cell_angle_beta 104.284(3) _cell_angle_gamma 90.00 _cell_volume 3296.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 1726 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.2 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1484 _exptl_absorpt_coefficient_mu 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.667 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21582 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 28.12 _reflns_number_total 7223 _reflns_number_gt 4270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0700P)^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 SHELXL _refine_ls_extinction_coef 0.0037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7223 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1365 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.22412(3) 0.186955(19) -0.10820(2) 0.02969(14) Uani 1 1 d . . . N11 N 0.3408(2) 0.18600(12) 0.01363(15) 0.0292(5) Uani 1 1 d . . . C12 C 0.4623(3) 0.19962(16) 0.02326(19) 0.0359(8) Uani 1 1 d . . . H12 H 0.4921 0.2041 -0.0281 0.043 Uiso 1 1 calc R . . C13 C 0.5450(3) 0.20730(16) 0.10465(18) 0.0334(7) Uani 1 1 d . . . H13 H 0.6289 0.2175 0.1083 0.040 Uiso 1 1 calc R . . C14 C 0.5035(3) 0.19979(14) 0.18146(18) 0.0278(7) Uani 1 1 d . . . C15 C 0.3792(3) 0.18419(16) 0.17242(18) 0.0354(7) Uani 1 1 d . . . H15 H 0.3483 0.1776 0.2230 0.042 Uiso 1 1 calc R . . C16 C 0.3008(3) 0.17845(16) 0.08844(19) 0.0350(7) Uani 1 1 d . . . H16 H 0.2161 0.1689 0.0832 0.042 Uiso 1 1 calc R . . C17 C 0.5977(3) 0.20943(16) 0.27009(18) 0.0314(7) Uani 1 1 d . . . N17 N 0.5563(2) 0.20572(13) 0.34325(15) 0.0362(6) Uani 1 1 d . . . H17A H 0.6079 0.2160 0.3832 0.043 Uiso 1 1 calc R . . H17B H 0.5000 0.1964 0.3434 0.043 Uiso 1 1 d R . . O17 O 0.70769(19) 0.22035(13) 0.27105(13) 0.0459(6) Uani 1 1 d . . . N21 N 0.1090(2) 0.19361(12) -0.23112(14) 0.0289(6) Uani 1 1 d . . . C22 C -0.0143(3) 0.20215(15) -0.24082(18) 0.0331(7) Uani 1 1 d . . . H22 H -0.0447 0.2036 -0.1895 0.040 Uiso 1 1 calc R . . C23 C -0.0980(3) 0.20886(15) -0.32239(18) 0.0313(7) Uani 1 1 d . . . H23 H -0.1834 0.2146 -0.3261 0.038 Uiso 1 1 calc R . . C24 C -0.0547(3) 0.20699(14) -0.39894(18) 0.0263(6) Uani 1 1 d . . . C25 C 0.0727(3) 0.19913(16) -0.38944(18) 0.0340(7) Uani 1 1 d . . . H25 H 0.1056 0.1984 -0.4397 0.041 Uiso 1 1 calc R . . C26 C 0.1502(3) 0.19243(15) -0.30550(18) 0.0323(7) Uani 1 1 d . . . H26 H 0.2360 0.1868 -0.3001 0.039 Uiso 1 1 calc R . . C27 C -0.1495(3) 0.21291(16) -0.48741(18) 0.0313(7) Uani 1 1 d . . . N27 N -0.1063(2) 0.21181(14) -0.56015(15) 0.0416(7) Uani 1 1 d . . . H27A H -0.1601 0.2161 -0.6010 0.050 Uiso 1 1 calc R . . H27B H -0.0429 0.2122 -0.5555 0.050 Uiso 1 1 d R . . O27 O -0.26057(19) 0.21667(14) -0.48873(13) 0.0476(6) Uani 1 1 d . . . C31 C 0.4178(3) 0.05749(18) -0.2417(2) 0.0490(9) Uani 1 1 d . . . F32 F 0.3573(3) -0.05655(13) -0.2624(2) 0.1062(10) Uani 1 1 d . . . C32 C 0.4326(4) -0.0062(2) -0.2745(3) 0.0697(12) Uani 1 1 d . . . C33 C 0.5222(5) -0.0212(2) -0.3190(4) 0.0972(18) Uani 1 1 d . . . H33 H 0.5282 -0.0652 -0.3405 0.117 Uiso 1 1 calc R . . C34 C 0.6004(6) 0.0269(3) -0.3314(4) 0.111(2) Uani 1 1 d . . . H34 H 0.6621 0.0166 -0.3614 0.133 Uiso 1 1 calc R . . C35 C 0.5915(5) 0.0918(3) -0.3005(4) 0.110(2) Uani 1 1 d . . . H35 H 0.6459 0.1256 -0.3107 0.132 Uiso 1 1 calc R . . C36 C 0.5016(4) 0.1072(2) -0.2541(3) 0.0729(13) Uani 1 1 d . . . H36 H 0.4976 0.1510 -0.2313 0.087 Uiso 1 1 calc R . . O37 O 0.34075(18) 0.12960(11) -0.14860(13) 0.0412(6) Uani 1 1 d . . . C37 C 0.3172(3) 0.07585(18) -0.1959(2) 0.0397(8) Uani 1 1 d . . . O38 O 0.2207(2) 0.04170(12) -0.20892(16) 0.0521(6) Uani 1 1 d . . . C41 C -0.0977(3) 0.06712(17) -0.0487(2) 0.0422(8) Uani 1 1 d . . . F42 F -0.0230(2) 0.13720(12) 0.07757(16) 0.0757(7) Uani 1 1 d . . . C42 C -0.1141(3) 0.09753(19) 0.0279(3) 0.0553(10) Uani 1 1 d . . . C43 C -0.2167(4) 0.0876(2) 0.0616(3) 0.0736(13) Uani 1 1 d . . . H43 H -0.2237 0.1091 0.1141 0.088 Uiso 1 1 calc R . . C44 C -0.3095(4) 0.0446(3) 0.0150(4) 0.0874(17) Uani 1 1 d . . . H44 H -0.3811 0.0371 0.0360 0.105 Uiso 1 1 calc R . . C45 C -0.2975(4) 0.0128(3) -0.0616(4) 0.0840(15) Uani 1 1 d . . . H45 H -0.3611 -0.0161 -0.0924 0.101 Uiso 1 1 calc R . . C46 C -0.1917(3) 0.0230(2) -0.0939(3) 0.0670(12) Uani 1 1 d . . . H46 H -0.1835 0.0005 -0.1455 0.080 Uiso 1 1 calc R . . O47 O 0.0271(2) 0.03798(12) -0.14603(17) 0.0523(6) Uani 1 1 d . . . H47 H 0.122(6) 0.036(3) -0.179(5) 0.21(3) Uiso 1 1 d . . . C47 C 0.0137(3) 0.08013(18) -0.0833(2) 0.0408(8) Uani 1 1 d . . . O48 O 0.0856(2) 0.12704(12) -0.05689(13) 0.0431(6) Uani 1 1 d . . . C51 C 0.1799(3) 0.39347(17) -0.0853(2) 0.0380(8) Uani 1 1 d . A . C52 C 0.2402(4) 0.4307(2) -0.0136(3) 0.0661(12) Uani 1 1 d . . . F52 F 0.3127(6) 0.3831(3) 0.0599(4) 0.072(3) Uani 0.326(5) 1 d P A 1 H52 H 0.3098 0.4118 0.0261 0.087 Uiso 0.674(5) 1 d PR A 2 C53 C 0.2034(5) 0.4951(3) 0.0028(5) 0.1037(19) Uani 1 1 d . A . H53 H 0.2460 0.5191 0.0535 0.124 Uiso 1 1 calc R . . C54 C 0.1050(7) 0.5228(3) -0.0553(5) 0.111(2) Uani 1 1 d . . . H54 H 0.0801 0.5670 -0.0452 0.133 Uiso 1 1 calc R A . C55 C 0.0410(7) 0.4883(3) -0.1283(4) 0.124(3) Uani 1 1 d . A . H55 H -0.0277 0.5078 -0.1685 0.149 Uiso 1 1 calc R . . C56 C 0.0804(5) 0.4245(3) -0.1408(3) 0.0879(17) Uani 1 1 d . . . H56 H 0.0363 0.4003 -0.1908 0.106 Uiso 0.326(5) 1 d PR A 1 F56 F 0.0022(4) 0.3757(2) -0.2055(2) 0.0957(17) Uani 0.674(5) 1 d P A 2 O57 O 0.3075(2) 0.31259(12) -0.13352(15) 0.0447(6) Uani 1 1 d . A . C57 C 0.2178(3) 0.32202(16) -0.10133(18) 0.0312(7) Uani 1 1 d . . . O58 O 0.15319(17) 0.27474(10) -0.07819(12) 0.0305(5) Uani 1 1 d . A . 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 0.0243(2) 0.0455(2) 0.01766(19) -0.00191(16) 0.00214(13) 0.00254(16) N11 0.0253(13) 0.0422(14) 0.0197(12) 0.0001(11) 0.0049(9) 0.0027(11) C12 0.0291(17) 0.058(2) 0.0208(15) 0.0043(14) 0.0072(12) -0.0045(14) C13 0.0233(16) 0.052(2) 0.0251(15) 0.0017(13) 0.0075(12) -0.0050(13) C14 0.0212(15) 0.0404(18) 0.0207(14) 0.0011(12) 0.0031(11) 0.0026(12) C15 0.0244(16) 0.064(2) 0.0190(14) -0.0011(14) 0.0069(11) -0.0020(15) C16 0.0215(15) 0.058(2) 0.0249(15) -0.0023(14) 0.0054(12) -0.0038(14) C17 0.0250(16) 0.0478(19) 0.0211(15) 0.0033(13) 0.0049(12) 0.0007(13) N17 0.0186(13) 0.0690(19) 0.0196(13) -0.0036(12) 0.0017(10) -0.0061(12) O17 0.0219(12) 0.0919(18) 0.0229(11) 0.0040(11) 0.0034(8) -0.0086(11) N21 0.0255(13) 0.0421(15) 0.0180(12) -0.0036(10) 0.0035(9) 0.0023(11) C22 0.0289(17) 0.054(2) 0.0181(14) -0.0002(13) 0.0080(12) 0.0069(14) C23 0.0225(15) 0.0477(19) 0.0240(15) -0.0024(13) 0.0060(12) 0.0018(13) C24 0.0228(15) 0.0348(16) 0.0212(14) -0.0010(12) 0.0051(11) 0.0001(12) C25 0.0269(16) 0.058(2) 0.0183(14) -0.0009(13) 0.0081(12) 0.0015(14) C26 0.0192(15) 0.054(2) 0.0232(15) 0.0012(14) 0.0036(11) 0.0022(13) C27 0.0284(17) 0.0485(19) 0.0169(14) -0.0015(13) 0.0054(12) -0.0018(14) N27 0.0206(13) 0.081(2) 0.0204(13) 0.0034(13) 0.0005(10) -0.0024(13) O27 0.0216(12) 0.0994(19) 0.0211(11) -0.0041(12) 0.0037(9) 0.0033(12) C31 0.055(2) 0.049(2) 0.051(2) -0.0067(17) 0.0259(18) 0.0077(18) F32 0.137(3) 0.0625(18) 0.145(3) -0.0233(17) 0.083(2) -0.0131(17) C32 0.095(3) 0.044(2) 0.087(3) -0.009(2) 0.056(3) -0.006(2) C33 0.129(5) 0.061(3) 0.135(5) -0.021(3) 0.098(4) 0.005(3) C34 0.126(5) 0.086(4) 0.163(6) -0.021(4) 0.114(5) 0.006(4) C35 0.101(4) 0.081(4) 0.181(6) -0.021(4) 0.100(4) -0.009(3) C36 0.061(3) 0.073(3) 0.103(4) -0.011(3) 0.054(3) -0.002(2) O37 0.0316(12) 0.0583(15) 0.0305(12) -0.0133(11) 0.0018(9) 0.0095(10) C37 0.041(2) 0.049(2) 0.0299(17) 0.0038(15) 0.0101(14) 0.0100(17) O38 0.0534(16) 0.0573(16) 0.0533(15) -0.0075(12) 0.0277(12) -0.0068(13) C41 0.0286(17) 0.044(2) 0.054(2) 0.0120(17) 0.0096(15) 0.0016(15) F42 0.0820(18) 0.0834(17) 0.0753(17) -0.0151(13) 0.0451(14) -0.0153(14) C42 0.044(2) 0.048(2) 0.079(3) 0.014(2) 0.026(2) 0.0014(18) C43 0.062(3) 0.072(3) 0.102(4) 0.022(3) 0.050(3) 0.014(2) C44 0.048(3) 0.087(4) 0.141(5) 0.037(4) 0.050(3) 0.009(3) C45 0.041(3) 0.081(3) 0.130(5) 0.014(3) 0.020(3) -0.017(2) C46 0.041(2) 0.071(3) 0.086(3) 0.013(2) 0.011(2) -0.006(2) O47 0.0494(15) 0.0535(16) 0.0561(16) -0.0077(12) 0.0170(12) -0.0088(12) C47 0.0357(19) 0.049(2) 0.0339(18) 0.0147(16) 0.0012(14) 0.0014(16) O48 0.0362(13) 0.0640(16) 0.0278(12) 0.0002(11) 0.0055(9) -0.0108(12) C51 0.0408(19) 0.047(2) 0.0321(17) 0.0121(15) 0.0192(14) 0.0060(15) C52 0.065(3) 0.057(3) 0.075(3) -0.014(2) 0.014(2) 0.008(2) F52 0.081(5) 0.061(5) 0.051(4) -0.016(3) -0.029(4) 0.014(4) C53 0.104(5) 0.070(4) 0.147(6) -0.044(4) 0.050(4) -0.006(3) C54 0.162(7) 0.067(4) 0.142(6) 0.032(4) 0.109(5) 0.033(4) C55 0.182(7) 0.131(5) 0.080(4) 0.064(4) 0.070(4) 0.113(5) C56 0.105(4) 0.110(4) 0.044(2) 0.003(3) 0.009(2) 0.059(3) F56 0.080(3) 0.131(4) 0.065(3) 0.021(2) -0.002(2) 0.044(3) O57 0.0316(13) 0.0589(15) 0.0506(14) 0.0026(12) 0.0233(11) 0.0046(11) C57 0.0211(15) 0.052(2) 0.0203(14) 0.0007(13) 0.0043(11) 0.0018(14) O58 0.0257(11) 0.0460(13) 0.0217(10) -0.0004(9) 0.0096(8) 0.0010(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 O37 1.936(2) . ? Cu1 O58 2.007(2) . ? Cu1 N11 2.011(2) . ? Cu1 N21 2.022(2) . ? Cu1 O48 2.235(2) . ? N11 C12 1.344(4) . ? N11 C16 1.350(4) . ? C12 C13 1.374(4) . ? C13 C14 1.388(4) . ? C14 C15 1.385(4) . ? C14 C17 1.520(4) . ? C15 C16 1.382(4) . ? C17 O17 1.234(3) . ? C17 N17 1.328(4) . ? N21 C26 1.343(4) . ? N21 C22 1.347(4) . ? C22 C23 1.380(4) . ? C23 C24 1.388(4) . ? C24 C25 1.391(4) . ? C24 C27 1.514(4) . ? C25 C26 1.379(4) . ? C27 O27 1.228(3) . ? C27 N27 1.331(4) . ? C31 C32 1.383(5) . ? C31 C36 1.398(5) . ? C31 C37 1.506(5) . ? F32 C32 1.342(5) . ? C32 C33 1.373(6) . ? C33 C34 1.332(6) . ? C34 C35 1.382(7) . ? C35 C36 1.399(6) . ? O37 C37 1.282(4) . ? C37 O38 1.239(4) . ? C41 C42 1.385(5) . ? C41 C46 1.406(5) . ? C41 C47 1.485(5) . ? F42 C42 1.359(4) . ? C42 C43 1.377(5) . ? C43 C44 1.392(7) . ? C44 C45 1.381(7) . ? C45 C46 1.399(6) . ? O47 C47 1.318(4) . ? C47 O48 1.225(4) . ? C51 C52 1.363(5) . ? C51 C56 1.365(5) . ? C51 C57 1.512(4) . ? C52 C53 1.380(6) . ? C52 F52 1.543(7) . ? C53 C54 1.347(8) . ? C54 C55 1.363(9) . ? C55 C56 1.366(7) . ? C56 F56 1.503(6) . ? O57 C57 1.232(3) . ? C57 O58 1.282(3) . ? 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 O37 Cu1 O58 155.86(9) . . ? O37 Cu1 N11 88.50(9) . . ? O58 Cu1 N11 89.27(9) . . ? O37 Cu1 N21 92.78(9) . . ? O58 Cu1 N21 88.33(8) . . ? N11 Cu1 N21 176.73(10) . . ? O37 Cu1 O48 112.14(10) . . ? O58 Cu1 O48 91.89(8) . . ? N11 Cu1 O48 89.89(9) . . ? N21 Cu1 O48 92.42(9) . . ? C12 N11 C16 117.3(2) . . ? C12 N11 Cu1 119.76(19) . . ? C16 N11 Cu1 122.62(19) . . ? N11 C12 C13 123.1(3) . . ? C12 C13 C14 119.5(3) . . ? C15 C14 C13 117.9(2) . . ? C15 C14 C17 124.3(3) . . ? C13 C14 C17 117.8(3) . . ? C16 C15 C14 119.5(3) . . ? N11 C16 C15 122.7(3) . . ? O17 C17 N17 123.2(3) . . ? O17 C17 C14 119.2(3) . . ? N17 C17 C14 117.6(3) . . ? C26 N21 C22 117.2(2) . . ? C26 N21 Cu1 122.76(19) . . ? C22 N21 Cu1 120.00(19) . . ? N21 C22 C23 123.3(3) . . ? C22 C23 C24 119.2(3) . . ? C23 C24 C25 117.9(2) . . ? C23 C24 C27 117.8(3) . . ? C25 C24 C27 124.3(3) . . ? C26 C25 C24 119.3(3) . . ? N21 C26 C25 123.1(3) . . ? O27 C27 N27 123.7(3) . . ? O27 C27 C24 119.2(3) . . ? N27 C27 C24 117.0(3) . . ? C32 C31 C36 116.5(4) . . ? C32 C31 C37 124.2(4) . . ? C36 C31 C37 119.3(3) . . ? F32 C32 C33 117.5(4) . . ? F32 C32 C31 119.3(4) . . ? C33 C32 C31 123.3(4) . . ? C34 C33 C32 119.6(4) . . ? C33 C34 C35 120.5(5) . . ? C34 C35 C36 120.1(5) . . ? C31 C36 C35 119.9(4) . . ? C37 O37 Cu1 127.9(2) . . ? O38 C37 O37 126.2(3) . . ? O38 C37 C31 120.1(3) . . ? O37 C37 C31 113.6(3) . . ? C42 C41 C46 117.4(4) . . ? C42 C41 C47 122.2(3) . . ? C46 C41 C47 120.5(4) . . ? F42 C42 C43 115.7(4) . . ? F42 C42 C41 120.1(3) . . ? C43 C42 C41 124.1(4) . . ? C42 C43 C44 117.6(5) . . ? C45 C44 C43 120.6(4) . . ? C44 C45 C46 120.7(4) . . ? C45 C46 C41 119.6(4) . . ? O48 C47 O47 122.9(3) . . ? O48 C47 C41 122.7(3) . . ? O47 C47 C41 114.4(3) . . ? C47 O48 Cu1 136.8(2) . . ? C52 C51 C56 115.5(4) . . ? C52 C51 C57 122.6(3) . . ? C56 C51 C57 121.9(3) . . ? C51 C52 C53 122.8(4) . . ? C51 C52 F52 109.6(4) . . ? C53 C52 F52 123.4(5) . . ? C54 C53 C52 118.6(5) . . ? C53 C54 C55 121.5(6) . . ? C54 C55 C56 117.5(5) . . ? C51 C56 C55 124.2(5) . . ? C51 C56 F56 112.1(4) . . ? C55 C56 F56 122.4(5) . . ? O57 C57 O58 124.5(3) . . ? O57 C57 C51 119.6(3) . . ? O58 C57 C51 116.0(3) . . ? C57 O58 Cu1 106.73(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O37 Cu1 N11 C12 49.5(2) . . . . ? O58 Cu1 N11 C12 -106.4(2) . . . . ? N21 Cu1 N11 C12 -63.4(17) . . . . ? O48 Cu1 N11 C12 161.7(2) . . . . ? O37 Cu1 N11 C16 -137.0(2) . . . . ? O58 Cu1 N11 C16 67.1(2) . . . . ? N21 Cu1 N11 C16 110.1(16) . . . . ? O48 Cu1 N11 C16 -24.8(2) . . . . ? C16 N11 C12 C13 -1.3(4) . . . . ? Cu1 N11 C12 C13 172.6(2) . . . . ? N11 C12 C13 C14 1.0(5) . . . . ? C12 C13 C14 C15 0.5(5) . . . . ? C12 C13 C14 C17 -179.4(3) . . . . ? C13 C14 C15 C16 -1.7(5) . . . . ? C17 C14 C15 C16 178.1(3) . . . . ? C12 N11 C16 C15 0.0(5) . . . . ? Cu1 N11 C16 C15 -173.7(2) . . . . ? C14 C15 C16 N11 1.5(5) . . . . ? C15 C14 C17 O17 176.8(3) . . . . ? C13 C14 C17 O17 -3.3(4) . . . . ? C15 C14 C17 N17 -3.3(4) . . . . ? C13 C14 C17 N17 176.5(3) . . . . ? O37 Cu1 N21 C26 -32.2(2) . . . . ? O58 Cu1 N21 C26 123.7(2) . . . . ? N11 Cu1 N21 C26 80.7(17) . . . . ? O48 Cu1 N21 C26 -144.5(2) . . . . ? O37 Cu1 N21 C22 150.4(2) . . . . ? O58 Cu1 N21 C22 -53.7(2) . . . . ? N11 Cu1 N21 C22 -96.8(17) . . . . ? O48 Cu1 N21 C22 38.1(2) . . . . ? C26 N21 C22 C23 0.7(4) . . . . ? Cu1 N21 C22 C23 178.3(2) . . . . ? N21 C22 C23 C24 -0.2(5) . . . . ? C22 C23 C24 C25 -0.7(4) . . . . ? C22 C23 C24 C27 178.6(3) . . . . ? C23 C24 C25 C26 1.1(4) . . . . ? C27 C24 C25 C26 -178.3(3) . . . . ? C22 N21 C26 C25 -0.3(4) . . . . ? Cu1 N21 C26 C25 -177.8(2) . . . . ? C24 C25 C26 N21 -0.5(5) . . . . ? C23 C24 C27 O27 -2.6(4) . . . . ? C25 C24 C27 O27 176.8(3) . . . . ? C23 C24 C27 N27 179.2(3) . . . . ? C25 C24 C27 N27 -1.4(4) . . . . ? C36 C31 C32 F32 178.1(4) . . . . ? C37 C31 C32 F32 -3.1(6) . . . . ? C36 C31 C32 C33 -1.3(7) . . . . ? C37 C31 C32 C33 177.5(4) . . . . ? F32 C32 C33 C34 -178.9(5) . . . . ? C31 C32 C33 C34 0.5(9) . . . . ? C32 C33 C34 C35 -0.5(10) . . . . ? C33 C34 C35 C36 1.4(10) . . . . ? C32 C31 C36 C35 2.2(7) . . . . ? C37 C31 C36 C35 -176.7(4) . . . . ? C34 C35 C36 C31 -2.2(9) . . . . ? O58 Cu1 O37 C37 -141.9(2) . . . . ? N11 Cu1 O37 C37 133.2(3) . . . . ? N21 Cu1 O37 C37 -49.8(3) . . . . ? O48 Cu1 O37 C37 44.0(3) . . . . ? Cu1 O37 C37 O38 -17.1(5) . . . . ? Cu1 O37 C37 C31 159.7(2) . . . . ? C32 C31 C37 O38 -22.3(5) . . . . ? C36 C31 C37 O38 156.5(4) . . . . ? C32 C31 C37 O37 160.6(4) . . . . ? C36 C31 C37 O37 -20.6(5) . . . . ? C46 C41 C42 F42 175.8(3) . . . . ? C47 C41 C42 F42 -4.6(5) . . . . ? C46 C41 C42 C43 -0.6(6) . . . . ? C47 C41 C42 C43 179.1(3) . . . . ? F42 C42 C43 C44 -176.9(4) . . . . ? C41 C42 C43 C44 -0.4(6) . . . . ? C42 C43 C44 C45 0.6(7) . . . . ? C43 C44 C45 C46 0.1(7) . . . . ? C44 C45 C46 C41 -1.2(7) . . . . ? C42 C41 C46 C45 1.3(5) . . . . ? C47 C41 C46 C45 -178.3(3) . . . . ? C42 C41 C47 O48 -14.0(5) . . . . ? C46 C41 C47 O48 165.7(3) . . . . ? C42 C41 C47 O47 167.5(3) . . . . ? C46 C41 C47 O47 -12.8(4) . . . . ? O47 C47 O48 Cu1 21.0(5) . . . . ? C41 C47 O48 Cu1 -157.4(2) . . . . ? O37 Cu1 O48 C47 -51.4(3) . . . . ? O58 Cu1 O48 C47 131.0(3) . . . . ? N11 Cu1 O48 C47 -139.8(3) . . . . ? N21 Cu1 O48 C47 42.6(3) . . . . ? C56 C51 C52 C53 0.6(7) . . . . ? C57 C51 C52 C53 -177.8(4) . . . . ? C56 C51 C52 F52 157.9(5) . . . . ? C57 C51 C52 F52 -20.5(6) . . . . ? C51 C52 C53 C54 -1.3(8) . . . . ? F52 C52 C53 C54 -155.5(6) . . . . ? C52 C53 C54 C55 1.0(9) . . . . ? C53 C54 C55 C56 -0.3(10) . . . . ? C52 C51 C56 C55 0.2(8) . . . . ? C57 C51 C56 C55 178.7(5) . . . . ? C52 C51 C56 F56 -167.1(4) . . . . ? C57 C51 C56 F56 11.4(6) . . . . ? C54 C55 C56 C51 -0.4(9) . . . . ? C54 C55 C56 F56 165.6(5) . . . . ? C52 C51 C57 O57 -79.4(4) . . . . ? C56 C51 C57 O57 102.3(4) . . . . ? C52 C51 C57 O58 99.5(4) . . . . ? C56 C51 C57 O58 -78.9(4) . . . . ? O57 C57 O58 Cu1 -1.6(3) . . . . ? C51 C57 O58 Cu1 179.59(19) . . . . ? O37 Cu1 O58 C57 5.3(3) . . . . ? N11 Cu1 O58 C57 90.02(17) . . . . ? N21 Cu1 O58 C57 -87.74(17) . . . . ? O48 Cu1 O58 C57 179.89(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N17 H17A O27 0.76 2.16 2.891(3) 162.9 1_656 N17 H17B O57 0.65 2.25 2.889(3) 165.4 4_566 N27 H27A O17 0.76 2.16 2.912(3) 170.3 1_454 N27 H27B O58 0.69 2.30 2.968(3) 164.5 4_565 _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 0.925 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.072 #===END