# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Dr Mir Wais Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur Strasbourg F-67000 FRANCE ; _publ_contact_author_email HOSSEINI@CHIMIE.U-STRASBG.FR _publ_section_title ; Molecular tectonics: design of coordinating tectons based on diazamacrocycles bearing pyridine units and formation of 1-D Copper coordination networks ; loop_ _publ_author_name 'Mir Wais Hosseini' 'Ernest Graf' 'Nathalie Kyritsakas' 'Jean-Marc Planeix' data_jmp114 _database_code_depnum_ccdc_archive 'CCDC 252123' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 Cu N2 O7' _chemical_formula_sum 'C16 H22 Cu N2 O7' _chemical_formula_weight 417.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8868(6) _cell_length_b 9.9720(7) _cell_length_c 10.5256(8) _cell_angle_alpha 75.286(3) _cell_angle_beta 81.777(3) _cell_angle_gamma 85.916(3) _cell_volume 892.31(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6064 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 25.66 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 1.555 _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 1.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8839 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 38050 _diffrn_reflns_av_R_equivalents 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 30.75 _reflns_number_total 5510 _reflns_number_gt 4193 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1246P)^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 5510 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1750 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 Cu1 Cu 0.44314(3) 0.90500(3) 0.45732(3) 0.02410(15) Uani 1 1 d . . . O18 O 0.6546(2) 0.8300(2) 0.4394(2) 0.0375(5) Uani 1 1 d . . . O19 O 0.7524(2) 0.9976(2) 0.5061(2) 0.0352(5) Uani 1 1 d . . . O20 O 0.4159(3) 0.7929(2) 0.6416(2) 0.0374(5) Uani 1 1 d . . . O9 O 0.2606(3) 0.4732(2) 0.0697(2) 0.0391(5) Uani 1 1 d . . . O17 O -0.1355(2) 0.6798(2) 0.17773(19) 0.0308(4) Uani 1 1 d . . . O16 O 0.0627(3) 0.1132(2) 0.0766(2) 0.0389(5) Uani 1 1 d . . . N1 N 0.3472(3) 0.7624(2) 0.3656(2) 0.0252(5) Uani 1 1 d . . . N2 N 0.0465(3) 0.4223(2) 0.2143(2) 0.0289(5) Uani 1 1 d . . . C1 C 0.3662(3) 0.6265(3) 0.4081(3) 0.0300(6) Uani 1 1 d . . . H1 H 0.4221 0.5912 0.4808 0.036 Uiso 1 1 calc R . . C2 C 0.3082(3) 0.5327(3) 0.3512(3) 0.0321(6) Uani 1 1 d . . . H2 H 0.3229 0.4356 0.3849 0.038 Uiso 1 1 calc R . . C3 C 0.2282(3) 0.5852(3) 0.2436(3) 0.0248(5) Uani 1 1 d . . . C4 C 0.2087(3) 0.7277(3) 0.1985(3) 0.0277(5) Uani 1 1 d . . . H4 H 0.1543 0.7664 0.1254 0.033 Uiso 1 1 calc R . . C5 C 0.2702(3) 0.8125(3) 0.2619(3) 0.0279(5) Uani 1 1 d . . . H5 H 0.2572 0.9102 0.2308 0.034 Uiso 1 1 calc R . . C6 C 0.1779(3) 0.4895(3) 0.1692(3) 0.0271(5) Uani 1 1 d . . . C10 C 0.0057(3) 0.3290(3) 0.1374(3) 0.0330(6) Uani 1 1 d . . . H10A H 0.0271 0.3741 0.0417 0.040 Uiso 1 1 calc R . . H10B H -0.1047 0.3129 0.1583 0.040 Uiso 1 1 calc R . . C7 C -0.0702(3) 0.4595(3) 0.3156(3) 0.0321(6) Uani 1 1 d . . . H7A H -0.0214 0.5066 0.3704 0.039 Uiso 1 1 calc R . . H7B H -0.1144 0.3736 0.3745 0.039 Uiso 1 1 calc R . . C8 C -0.1974(3) 0.5542(3) 0.2549(3) 0.0324(6) Uani 1 1 d . . . H8A H -0.2462 0.5087 0.1988 0.039 Uiso 1 1 calc R . . H8B H -0.2757 0.5727 0.3259 0.039 Uiso 1 1 calc R . . C9 C -0.2507(3) 0.7658(3) 0.1099(3) 0.0355(6) Uani 1 1 d . . . H9A H -0.3348 0.7866 0.1754 0.043 Uiso 1 1 calc R . . H9B H -0.2927 0.7157 0.0535 0.043 Uiso 1 1 calc R . . C13 C 0.7638(3) 0.8905(3) 0.4618(3) 0.0273(5) Uani 1 1 d . . . C14 C 0.9212(3) 0.8306(4) 0.4321(4) 0.0415(7) Uani 1 1 d . . . H14A H 0.9235 0.7306 0.4727 0.062 Uiso 1 1 calc R . . H14B H 0.9940 0.8752 0.4684 0.062 Uiso 1 1 calc R . . H14C H 0.9485 0.8468 0.3360 0.062 Uiso 1 1 calc R . . C15 C 0.4561(3) 0.8405(3) 0.7324(3) 0.0293(6) Uani 1 1 d . . . C16 C 0.4309(4) 0.7530(4) 0.8722(3) 0.0413(7) Uani 1 1 d . . . H16A H 0.3294 0.7147 0.8898 0.062 Uiso 1 1 calc R . . H16B H 0.4391 0.8103 0.9338 0.062 Uiso 1 1 calc R . . H16C H 0.5079 0.6770 0.8840 0.062 Uiso 1 1 calc R . . C11 C 0.0932(4) 0.1903(3) 0.1668(3) 0.0361(6) Uani 1 1 d . . . H11A H 0.2036 0.2054 0.1567 0.043 Uiso 1 1 calc R . . H11B H 0.0612 0.1380 0.2591 0.043 Uiso 1 1 calc R . . C12 C 0.1846(4) 0.1005(3) -0.0250(3) 0.0396(7) Uani 1 1 d . . . H12A H 0.1476 0.0503 -0.0837 0.048 Uiso 1 1 calc R . . H12B H 0.2675 0.0424 0.0174 0.048 Uiso 1 1 calc R . . O21 O 0.5141(3) 0.9578(2) 0.7142(2) 0.0369(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 0.0165(2) 0.0276(2) 0.0309(2) -0.01420(15) -0.00065(13) 0.00199(13) O18 0.0205(10) 0.0421(11) 0.0584(14) -0.0300(10) -0.0048(9) 0.0065(9) O19 0.0181(9) 0.0393(11) 0.0552(13) -0.0280(10) -0.0026(9) 0.0066(8) O20 0.0431(13) 0.0350(11) 0.0340(11) -0.0064(9) -0.0051(9) -0.0090(10) O9 0.0374(12) 0.0434(12) 0.0396(11) -0.0228(9) 0.0106(9) -0.0080(10) O17 0.0230(9) 0.0346(10) 0.0367(10) -0.0140(8) -0.0024(8) 0.0029(8) O16 0.0436(13) 0.0350(11) 0.0429(11) -0.0200(9) 0.0007(9) -0.0089(10) N1 0.0176(10) 0.0320(11) 0.0280(11) -0.0132(9) -0.0014(8) 0.0044(9) N2 0.0195(10) 0.0346(12) 0.0376(13) -0.0201(10) -0.0015(9) 0.0017(9) C1 0.0271(13) 0.0321(13) 0.0336(14) -0.0123(11) -0.0078(11) 0.0025(11) C2 0.0345(15) 0.0256(12) 0.0387(15) -0.0117(11) -0.0083(12) 0.0019(11) C3 0.0173(11) 0.0291(13) 0.0304(13) -0.0139(10) 0.0007(10) -0.0007(10) C4 0.0206(12) 0.0330(13) 0.0306(13) -0.0113(11) -0.0033(10) 0.0036(10) C5 0.0233(13) 0.0277(12) 0.0335(13) -0.0114(10) -0.0018(10) 0.0052(10) C6 0.0268(13) 0.0255(12) 0.0322(14) -0.0132(10) -0.0045(11) 0.0017(10) C10 0.0236(13) 0.0365(14) 0.0457(17) -0.0207(13) -0.0074(12) -0.0019(11) C7 0.0219(13) 0.0388(15) 0.0356(14) -0.0138(12) 0.0028(11) 0.0028(11) C8 0.0187(12) 0.0412(15) 0.0360(15) -0.0110(12) 0.0019(11) 0.0020(11) C9 0.0274(14) 0.0418(16) 0.0404(16) -0.0163(13) -0.0079(12) 0.0076(12) C13 0.0195(12) 0.0333(13) 0.0305(13) -0.0137(11) -0.0005(10) 0.0050(10) C14 0.0204(13) 0.0503(18) 0.061(2) -0.0308(16) -0.0061(13) 0.0133(13) C15 0.0176(12) 0.0361(14) 0.0334(14) -0.0093(11) -0.0006(10) 0.0018(10) C16 0.0342(16) 0.0516(19) 0.0350(16) -0.0034(14) -0.0041(13) -0.0081(14) C11 0.0420(17) 0.0303(14) 0.0394(15) -0.0150(12) -0.0049(13) -0.0019(13) C12 0.0427(18) 0.0379(15) 0.0423(17) -0.0195(13) -0.0064(14) 0.0085(14) O21 0.0413(13) 0.0393(11) 0.0310(11) -0.0094(9) -0.0025(9) -0.0098(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 O19 1.9669(19) 2_676 ? Cu1 O20 1.968(2) . ? Cu1 O18 1.974(2) . ? Cu1 O21 1.974(2) 2_676 ? Cu1 N1 2.187(2) . ? Cu1 Cu1 2.6107(6) 2_676 ? O18 C13 1.258(3) . ? O19 C13 1.262(3) . ? O19 Cu1 1.9669(19) 2_676 ? O20 C15 1.272(3) . ? O9 C6 1.230(3) . ? O17 C8 1.409(4) . ? O17 C9 1.437(3) . ? O16 C11 1.428(3) . ? O16 C12 1.432(4) . ? N1 C1 1.321(4) . ? N1 C5 1.341(4) . ? N2 C6 1.353(4) . ? N2 C10 1.472(3) . ? N2 C7 1.476(3) . ? C1 C2 1.393(4) . ? C2 C3 1.392(4) . ? C3 C4 1.386(4) . ? C3 C6 1.505(4) . ? C4 C5 1.384(4) . ? C10 C11 1.520(4) . ? C7 C8 1.526(4) . ? C9 C12 1.509(5) 2_565 ? C13 C14 1.503(4) . ? C15 O21 1.271(4) . ? C15 C16 1.502(4) . ? C12 C9 1.509(5) 2_565 ? O21 Cu1 1.974(2) 2_676 ? 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 O19 Cu1 O20 88.85(10) 2_676 . ? O19 Cu1 O18 168.97(8) 2_676 . ? O20 Cu1 O18 88.63(10) . . ? O19 Cu1 O21 90.18(10) 2_676 2_676 ? O20 Cu1 O21 169.61(8) . 2_676 ? O18 Cu1 O21 90.36(10) . 2_676 ? O19 Cu1 N1 94.53(8) 2_676 . ? O20 Cu1 N1 98.21(9) . . ? O18 Cu1 N1 96.47(8) . . ? O21 Cu1 N1 92.18(9) 2_676 . ? O19 Cu1 Cu1 84.34(6) 2_676 2_676 ? O20 Cu1 Cu1 87.81(6) . 2_676 ? O18 Cu1 Cu1 84.83(6) . 2_676 ? O21 Cu1 Cu1 81.80(6) 2_676 2_676 ? N1 Cu1 Cu1 173.86(6) . 2_676 ? C13 O18 Cu1 122.14(18) . . ? C13 O19 Cu1 123.05(18) . 2_676 ? C15 O20 Cu1 119.41(19) . . ? C8 O17 C9 110.0(2) . . ? C11 O16 C12 116.0(2) . . ? C1 N1 C5 118.5(2) . . ? C1 N1 Cu1 121.47(18) . . ? C5 N1 Cu1 119.98(19) . . ? C6 N2 C10 116.7(2) . . ? C6 N2 C7 123.5(2) . . ? C10 N2 C7 118.5(2) . . ? N1 C1 C2 123.0(3) . . ? C3 C2 C1 118.2(3) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 C6 120.5(2) . . ? C2 C3 C6 120.4(2) . . ? C5 C4 C3 118.6(2) . . ? N1 C5 C4 122.7(3) . . ? O9 C6 N2 122.1(2) . . ? O9 C6 C3 118.2(2) . . ? N2 C6 C3 119.7(2) . . ? N2 C10 C11 112.2(2) . . ? N2 C7 C8 112.4(2) . . ? O17 C8 C7 109.0(2) . . ? O17 C9 C12 110.3(2) . 2_565 ? O18 C13 O19 125.5(2) . . ? O18 C13 C14 117.1(2) . . ? O19 C13 C14 117.4(2) . . ? O21 C15 O20 124.9(3) . . ? O21 C15 C16 117.3(3) . . ? O20 C15 C16 117.8(3) . . ? O16 C11 C10 108.8(2) . . ? O16 C12 C9 116.4(2) . 2_565 ? C15 O21 Cu1 126.11(19) . 2_676 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.75 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.660 _refine_diff_density_min -1.655 _refine_diff_density_rms 0.248 data_e14n _database_code_depnum_ccdc_archive 'CCDC 252124' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H52 Cu2 N4 O14' _chemical_formula_weight 903.91 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 8.6452(2) _cell_length_b 11.4949(3) _cell_length_c 12.4095(3) _cell_angle_alpha 108.692(2) _cell_angle_beta 93.096(2) _cell_angle_gamma 107.264(2) _cell_volume 1100.27(5) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6706 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 29.41 _exptl_crystal_description plate _exptl_crystal_colour clear _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 1.364 _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 53993 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 36.58 _reflns_number_total 9964 _reflns_number_gt 7098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1303P)^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 9964 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.016 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 C18 C 0.4285(6) 0.9433(6) 0.4942(4) 0.0882(17) Uani 1 1 d . . . C19 C 0.7066(9) 1.0365(7) 0.4569(6) 0.064(2) Uani 0.50 1 d P . . C20 C 0.7091(7) 0.9177(6) 0.3969(6) 0.0490(14) Uani 0.50 1 d P . . C1 C 0.9039(3) 0.7939(2) 0.77835(17) 0.0283(4) Uani 1 1 d . . . H1 H 0.9115 0.7276 0.8064 0.034 Uiso 1 1 calc R . . C2 C 0.8642(3) 0.8976(2) 0.85084(17) 0.0296(4) Uani 1 1 d . . . H2 H 0.8455 0.9016 0.9265 0.036 Uiso 1 1 calc R . . C3 C 0.8525(3) 0.99388(19) 0.81140(16) 0.0249(4) Uani 1 1 d . . . C4 C 0.8763(5) 0.9817(3) 0.7001(2) 0.0523(8) Uani 1 1 d . . . H4 H 0.8669 1.0455 0.6693 0.063 Uiso 1 1 calc R . . C5 C 0.9146(4) 0.8742(3) 0.6335(2) 0.0483(7) Uani 1 1 d . . . H5 H 0.9291 0.8658 0.5564 0.058 Uiso 1 1 calc R . . C6 C 0.8239(3) 1.11256(19) 0.89271(16) 0.0258(4) Uani 1 1 d . . . C7 C 0.5299(3) 1.0243(2) 0.80342(18) 0.0312(4) Uani 1 1 d . . . H7A H 0.5692 0.9643 0.7437 0.037 Uiso 1 1 calc R . . H7B H 0.4823 1.0728 0.7657 0.037 Uiso 1 1 calc R . . C8 C 0.3958(3) 0.9446(2) 0.84962(18) 0.0313(4) Uani 1 1 d . . . H8A H 0.3622 1.0026 0.9149 0.038 Uiso 1 1 calc R . . H8B H 0.2986 0.8930 0.7885 0.038 Uiso 1 1 calc R . . C9 C 0.3345(3) 0.7560(2) 0.90355(18) 0.0337(5) Uani 1 1 d . . . H9A H 0.3420 0.6717 0.8540 0.040 Uiso 1 1 calc R . . H9B H 0.2251 0.7592 0.8795 0.040 Uiso 1 1 calc R . . C10 C 0.3509(3) 0.7642(2) 1.02855(18) 0.0304(4) Uani 1 1 d . . . H10A H 0.2686 0.6864 1.0344 0.036 Uiso 1 1 calc R . . H10B H 0.4612 0.7625 1.0525 0.036 Uiso 1 1 calc R . . C11 C 1.3054(2) 0.60342(19) 0.57576(16) 0.0237(3) Uani 1 1 d . . . C12 C 1.4867(3) 0.6617(2) 0.6222(2) 0.0352(5) Uani 1 1 d . . . H12A H 1.5316 0.7438 0.6087 0.053 Uiso 1 1 calc R . . H12B H 1.5421 0.6010 0.5830 0.053 Uiso 1 1 calc R . . H12C H 1.5042 0.6783 0.7052 0.053 Uiso 1 1 calc R . . C13 C 1.0312(3) 0.5832(2) 0.33271(17) 0.0271(4) Uani 1 1 d . . . C14 C 1.0474(4) 0.6295(3) 0.2313(2) 0.0495(7) Uani 1 1 d . . . H14A H 1.1477 0.7048 0.2494 0.074 Uiso 1 1 calc R . . H14B H 0.9519 0.6545 0.2157 0.074 Uiso 1 1 calc R . . H14C H 1.0530 0.5592 0.1632 0.074 Uiso 1 1 calc R . . C15 C 0.6033(10) 0.6707(7) 0.3145(5) 0.0571(17) Uani 0.50 1 d P . . C16 C 0.5798(9) 0.8077(7) 0.3863(6) 0.0549(17) Uani 0.50 1 d P . . C17 C 0.4416(9) 0.8237(12) 0.4363(8) 0.093(4) Uani 0.50 1 d P . . C21 C 0.3203(7) 0.3944(6) 0.0453(6) 0.1090(18) Uani 1 1 d . . . H21A H 0.3416 0.3724 0.1135 0.163 Uiso 1 1 calc R . . H21B H 0.2364 0.4368 0.0556 0.163 Uiso 1 1 calc R . . H21C H 0.4218 0.4536 0.0353 0.163 Uiso 1 1 calc R . . Cu1 Cu 0.97841(3) 0.60858(2) 0.562389(18) 0.01930(8) Uani 1 1 d . . . N1 N 0.9318(2) 0.78304(17) 0.67206(14) 0.0232(3) Uani 1 1 d . . . N2 N 0.6718(2) 1.11788(17) 0.89135(14) 0.0257(3) Uani 1 1 d . . . O1 O 0.9435(2) 1.20026(16) 0.96039(14) 0.0346(3) Uani 1 1 d . . . O2 O 0.45895(19) 0.85985(15) 0.88715(13) 0.0296(3) Uani 1 1 d . . . O3 O 1.21748(18) 0.67364(15) 0.61036(13) 0.0287(3) Uani 1 1 d . . . O4 O 1.25298(19) 0.48751(16) 0.50558(16) 0.0355(4) Uani 1 1 d . . . O5 O 0.9565(2) 0.52655(17) 0.68164(14) 0.0350(4) Uani 1 1 d . . . O6 O 1.0076(2) 0.65844(16) 0.42452(13) 0.0312(3) Uani 1 1 d . . . O7 O 0.2623(4) 0.2757(4) -0.0565(3) 0.1057(12) Uani 1 1 d . . . H7 H 0.1603 0.2412 -0.0629 0.159 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 C18 0.101(4) 0.158(6) 0.0448(18) 0.049(3) 0.022(2) 0.082(4) C19 0.060(4) 0.063(4) 0.058(4) 0.030(3) -0.023(3) 0.003(3) C20 0.036(3) 0.051(3) 0.064(4) 0.033(3) -0.005(2) 0.006(2) C1 0.0405(11) 0.0244(9) 0.0265(9) 0.0083(7) 0.0110(8) 0.0198(8) C2 0.0450(12) 0.0283(9) 0.0230(8) 0.0085(7) 0.0132(8) 0.0222(9) C3 0.0339(10) 0.0226(8) 0.0201(8) 0.0039(6) 0.0070(7) 0.0159(7) C4 0.111(3) 0.0434(14) 0.0314(11) 0.0201(10) 0.0331(14) 0.0550(17) C5 0.097(2) 0.0414(13) 0.0271(10) 0.0148(9) 0.0299(13) 0.0464(16) C6 0.0402(11) 0.0222(8) 0.0197(8) 0.0063(6) 0.0094(7) 0.0176(8) C7 0.0410(12) 0.0307(10) 0.0238(9) 0.0065(7) 0.0022(8) 0.0185(9) C8 0.0321(10) 0.0336(10) 0.0270(9) 0.0032(8) 0.0038(8) 0.0174(9) C9 0.0389(12) 0.0280(10) 0.0269(9) 0.0004(8) 0.0112(8) 0.0098(9) C10 0.0429(12) 0.0243(9) 0.0282(9) 0.0056(7) 0.0126(8) 0.0201(9) C11 0.0205(8) 0.0255(8) 0.0220(8) 0.0040(6) 0.0069(6) 0.0076(7) C12 0.0189(8) 0.0367(11) 0.0352(10) -0.0050(9) 0.0034(8) 0.0075(8) C13 0.0315(10) 0.0268(9) 0.0257(9) 0.0122(7) 0.0077(7) 0.0098(8) C14 0.075(2) 0.0486(15) 0.0366(13) 0.0264(11) 0.0180(13) 0.0230(15) C15 0.083(5) 0.050(3) 0.043(3) 0.022(3) -0.008(3) 0.028(3) C16 0.054(3) 0.053(4) 0.056(4) 0.034(3) -0.009(3) 0.001(3) C17 0.039(3) 0.151(9) 0.083(5) 0.092(6) -0.016(4) -0.026(4) C21 0.075(3) 0.105(4) 0.147(5) 0.050(4) 0.052(3) 0.018(3) Cu1 0.01984(12) 0.01667(11) 0.02066(12) 0.00292(8) 0.00516(8) 0.00868(8) N1 0.0267(8) 0.0215(7) 0.0216(7) 0.0034(5) 0.0048(6) 0.0126(6) N2 0.0362(9) 0.0237(7) 0.0206(7) 0.0056(6) 0.0085(6) 0.0167(7) O1 0.0382(9) 0.0290(8) 0.0307(7) 0.0006(6) 0.0051(6) 0.0135(7) O2 0.0312(8) 0.0314(7) 0.0262(7) 0.0073(6) 0.0070(6) 0.0132(6) O3 0.0225(6) 0.0247(7) 0.0317(7) -0.0018(5) 0.0015(5) 0.0108(5) O4 0.0207(7) 0.0265(7) 0.0452(9) -0.0062(6) 0.0031(6) 0.0089(6) O5 0.0551(11) 0.0300(8) 0.0292(7) 0.0140(6) 0.0193(7) 0.0212(7) O6 0.0442(9) 0.0266(7) 0.0267(7) 0.0100(6) 0.0065(6) 0.0166(7) O7 0.066(2) 0.147(4) 0.112(3) 0.040(3) 0.0315(19) 0.049(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 C18 C17 1.374(14) . ? C18 C19 1.391(10) 2_676 ? C18 C18 1.467(12) 2_676 ? C19 C20 1.337(11) . ? C19 C18 1.391(10) 2_676 ? C20 C16 1.380(8) . ? C1 N1 1.327(3) . ? C1 C2 1.392(3) . ? C2 C3 1.373(3) . ? C3 C4 1.377(3) . ? C3 C6 1.511(3) . ? C4 C5 1.391(3) . ? C5 N1 1.325(3) . ? C6 O1 1.239(3) . ? C6 N2 1.335(3) . ? C7 N2 1.474(3) . ? C7 C8 1.514(3) . ? C8 O2 1.429(3) . ? C9 O2 1.429(3) . ? C9 C10 1.520(3) . ? C10 N2 1.477(2) 2_677 ? C11 O3 1.261(2) . ? C11 O4 1.263(2) . ? C11 C12 1.506(3) . ? C13 O5 1.254(3) 2_766 ? C13 O6 1.260(2) . ? C13 C14 1.514(3) . ? C15 C16 1.621(11) . ? C16 C17 1.408(13) . ? C21 O7 1.460(7) . ? Cu1 O4 1.9602(16) 2_766 ? Cu1 O3 1.9621(15) . ? Cu1 O6 1.9770(16) . ? Cu1 O5 1.9833(16) . ? Cu1 N1 2.1970(16) . ? Cu1 Cu1 2.6279(4) 2_766 ? N2 C10 1.477(2) 2_677 ? O4 Cu1 1.9602(16) 2_766 ? O5 C13 1.254(3) 2_766 ? 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 C17 C18 C19 125.2(6) . 2_676 ? C17 C18 C18 116.0(6) . 2_676 ? C19 C18 C18 118.9(7) 2_676 2_676 ? C20 C19 C18 122.3(7) . 2_676 ? C19 C20 C16 121.0(7) . . ? N1 C1 C2 123.23(19) . . ? C3 C2 C1 119.01(18) . . ? C2 C3 C4 118.26(18) . . ? C2 C3 C6 119.40(17) . . ? C4 C3 C6 122.24(19) . . ? C3 C4 C5 118.8(2) . . ? N1 C5 C4 123.5(2) . . ? O1 C6 N2 122.48(18) . . ? O1 C6 C3 118.20(19) . . ? N2 C6 C3 119.30(19) . . ? N2 C7 C8 114.50(17) . . ? O2 C8 C7 108.00(18) . . ? O2 C9 C10 111.80(18) . . ? N2 C10 C9 113.48(18) 2_677 . ? O3 C11 O4 125.00(19) . . ? O3 C11 C12 117.63(18) . . ? O4 C11 C12 117.36(18) . . ? O5 C13 O6 125.54(19) 2_766 . ? O5 C13 C14 117.2(2) 2_766 . ? O6 C13 C14 117.3(2) . . ? C20 C16 C17 118.3(8) . . ? C20 C16 C15 115.3(7) . . ? C17 C16 C15 126.4(7) . . ? C18 C17 C16 123.3(7) . . ? O4 Cu1 O3 168.58(6) 2_766 . ? O4 Cu1 O6 88.46(8) 2_766 . ? O3 Cu1 O6 89.89(7) . . ? O4 Cu1 O5 90.43(8) 2_766 . ? O3 Cu1 O5 88.96(8) . . ? O6 Cu1 O5 168.61(6) . . ? O4 Cu1 N1 94.60(6) 2_766 . ? O3 Cu1 N1 96.82(6) . . ? O6 Cu1 N1 97.52(6) . . ? O5 Cu1 N1 93.87(7) . . ? O4 Cu1 Cu1 83.50(5) 2_766 2_766 ? O3 Cu1 Cu1 85.11(4) . 2_766 ? O6 Cu1 Cu1 85.50(5) . 2_766 ? O5 Cu1 Cu1 83.10(5) . 2_766 ? N1 Cu1 Cu1 176.40(5) . 2_766 ? C5 N1 C1 117.21(17) . . ? C5 N1 Cu1 122.77(14) . . ? C1 N1 Cu1 119.71(13) . . ? C6 N2 C7 124.20(17) . . ? C6 N2 C10 117.69(18) . 2_677 ? C7 N2 C10 117.36(18) . 2_677 ? C8 O2 C9 113.52(18) . . ? C11 O3 Cu1 122.19(13) . . ? C11 O4 Cu1 124.17(13) . 2_766 ? C13 O5 Cu1 124.23(14) 2_766 . ? C13 O6 Cu1 121.60(14) . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 36.58 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 1.859 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.145