Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name "Prof Richard O'Hair" _publ_contact_author_address ; School of Chemistry University of Melbourne Melbourne Victoria 3010 AUSTRALIA ; _publ_contact_author_email ROHAIR@UNIMELB.EDU.AU _publ_section_title ; Tuning the Gas Phase Redox Properties of Copper(II) Ternary Complexes of Terpyridines to Control the Formation of Nucleobase Radical Cations ; loop_ _publ_author_name "Richard O'Hair" 'Brendan F. Abrahams' 'Martin J. Granna' 'Adrian K. Y. Lam' 'W. David McFadyen' data_adr5br1a _database_code_depnum_ccdc_archive 'CCDC 614030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Dinitrato(dibromoterpyrdine)copper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H9 Br2 Cu N5 O6' _chemical_formula_weight 578.63 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.550(2) _cell_length_b 17.238(5) _cell_length_c 14.203(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.687(6) _cell_angle_gamma 90.00 _cell_volume 1803.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2381 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 22.08 _exptl_crystal_description 'irregular block' _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 5.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.610 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; SADABS - SADABS: Area-Detector Absorption Correction; Siemens Industrial Automation, Inc.: Madison, WI, 1996. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker 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_% 0 _diffrn_reflns_number 11219 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4094 _reflns_number_gt 2734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0457P)^2^+0.8275P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4094 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.59968(7) 0.12530(3) 0.79942(4) 0.04558(17) Uani 1 1 d . . . Br2 Br 0.51908(10) 0.18683(4) 0.55668(4) 0.0894(2) Uani 1 1 d . . . Br1 Br 0.40786(9) 0.28675(3) 0.89787(5) 0.0842(2) Uani 1 1 d . . . O1 O 0.7007(4) 0.23156(17) 0.7750(2) 0.0539(8) Uani 1 1 d . . . O2 O 0.9402(5) 0.1828(2) 0.8648(3) 0.0747(10) Uani 1 1 d . . . O3 O 0.9472(5) 0.29874(18) 0.8084(2) 0.0654(9) Uani 1 1 d . . . O4 O 0.3305(5) 0.1504(2) 0.7374(3) 0.0781(11) Uani 1 1 d . . . O5 O 0.2878(6) 0.0300(3) 0.7416(4) 0.132(2) Uani 1 1 d . . . O6 O 0.0764(5) 0.1029(3) 0.6670(3) 0.1023(15) Uani 1 1 d . . . N1 N 0.5866(5) 0.1478(2) 0.9415(2) 0.0464(8) Uani 1 1 d . . . N2 N 0.7051(4) 0.03047(19) 0.8609(3) 0.0447(8) Uani 1 1 d . . . N3 N 0.6595(5) 0.0689(2) 0.6826(3) 0.0486(9) Uani 1 1 d . . . N4 N 0.8673(5) 0.2379(2) 0.8167(2) 0.0467(8) Uani 1 1 d . . . N5 N 0.2297(6) 0.0929(3) 0.7158(3) 0.0627(11) Uani 1 1 d . . . C1 C 0.5316(6) 0.2110(3) 0.9798(4) 0.0594(13) Uani 1 1 d . . . C2 C 0.5546(8) 0.2226(4) 1.0779(5) 0.0817(18) Uani 1 1 d . . . H2A H 0.5154 0.2682 1.1019 0.098 Uiso 1 1 calc R . . C3 C 0.6351(9) 0.1664(5) 1.1378(4) 0.093(2) Uani 1 1 d . . . H3A H 0.6536 0.1730 1.2043 0.112 Uiso 1 1 calc R . . C4 C 0.6900(7) 0.0991(4) 1.1008(4) 0.0773(17) Uani 1 1 d . . . H4 H 0.7437 0.0596 1.1420 0.093 Uiso 1 1 calc R . . C5 C 0.6648(6) 0.0905(3) 1.0023(3) 0.0520(11) Uani 1 1 d . . . C6 C 0.7215(6) 0.0224(2) 0.9556(3) 0.0487(11) Uani 1 1 d . . . C7 C 0.7890(6) -0.0460(3) 1.0003(4) 0.0645(14) Uani 1 1 d . . . H7 H 0.8015 -0.0523 1.0665 0.077 Uiso 1 1 calc R . . C8 C 0.8370(7) -0.1040(3) 0.9459(5) 0.0746(17) Uani 1 1 d . . . H8 H 0.8809 -0.1505 0.9750 0.090 Uiso 1 1 calc R . . C9 C 0.8214(7) -0.0948(3) 0.8491(4) 0.0670(14) Uani 1 1 d . . . H9 H 0.8544 -0.1345 0.8120 0.080 Uiso 1 1 calc R . . C10 C 0.7555(6) -0.0250(2) 0.8073(3) 0.0503(11) Uani 1 1 d . . . C11 C 0.7350(6) -0.0025(3) 0.7048(3) 0.0534(11) Uani 1 1 d . . . C12 C 0.7925(7) -0.0483(3) 0.6374(4) 0.0714(15) Uani 1 1 d . . . H12 H 0.8423 -0.0970 0.6541 0.086 Uiso 1 1 calc R . . C13 C 0.7748(8) -0.0207(4) 0.5460(5) 0.084(2) Uani 1 1 d . . . H13 H 0.8156 -0.0502 0.5001 0.101 Uiso 1 1 calc R . . C14 C 0.6967(8) 0.0507(4) 0.5214(4) 0.0774(17) Uani 1 1 d . . . H14 H 0.6836 0.0700 0.4591 0.093 Uiso 1 1 calc R . . C15 C 0.6385(7) 0.0928(3) 0.5913(3) 0.0603(13) 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 0.0542(3) 0.0389(3) 0.0428(3) 0.0033(2) 0.0087(2) -0.0012(2) Br2 0.1285(6) 0.0759(4) 0.0523(3) 0.0183(3) -0.0051(3) -0.0223(4) Br1 0.0849(4) 0.0628(4) 0.1074(5) -0.0139(3) 0.0269(4) 0.0154(3) O1 0.0491(18) 0.0500(17) 0.0559(19) 0.0119(15) -0.0028(15) -0.0080(14) O2 0.060(2) 0.062(2) 0.090(3) 0.022(2) -0.0093(19) -0.0042(17) O3 0.067(2) 0.059(2) 0.067(2) 0.0089(17) 0.0095(17) -0.0268(17) O4 0.049(2) 0.076(2) 0.101(3) -0.015(2) -0.0023(19) -0.0037(18) O5 0.092(3) 0.089(3) 0.199(6) 0.075(4) -0.003(3) -0.018(3) O6 0.063(3) 0.102(3) 0.119(4) 0.024(3) -0.029(2) -0.026(2) N1 0.047(2) 0.048(2) 0.046(2) -0.0044(17) 0.0146(17) -0.0102(16) N2 0.045(2) 0.0364(19) 0.051(2) 0.0022(16) 0.0056(16) -0.0038(15) N3 0.051(2) 0.048(2) 0.046(2) -0.0062(17) 0.0083(16) -0.0116(17) N4 0.052(2) 0.050(2) 0.0369(19) 0.0008(17) 0.0076(17) -0.0061(18) N5 0.055(3) 0.071(3) 0.057(2) 0.015(2) 0.003(2) -0.015(2) C1 0.050(3) 0.065(3) 0.067(3) -0.018(3) 0.022(2) -0.009(2) C2 0.068(4) 0.101(5) 0.076(4) -0.031(4) 0.016(3) -0.008(3) C3 0.081(4) 0.147(7) 0.053(3) -0.032(4) 0.019(3) -0.009(4) C4 0.066(3) 0.118(5) 0.046(3) 0.008(3) 0.007(3) -0.007(3) C5 0.048(3) 0.064(3) 0.044(2) 0.002(2) 0.009(2) -0.015(2) C6 0.045(2) 0.048(3) 0.048(3) 0.012(2) 0.000(2) -0.0072(19) C7 0.059(3) 0.066(3) 0.061(3) 0.022(3) -0.003(2) -0.012(3) C8 0.066(3) 0.046(3) 0.096(5) 0.018(3) -0.015(3) -0.001(2) C9 0.057(3) 0.044(3) 0.090(4) -0.009(3) -0.003(3) 0.002(2) C10 0.046(2) 0.041(2) 0.059(3) -0.005(2) 0.001(2) -0.0037(19) C11 0.045(2) 0.051(3) 0.065(3) -0.016(2) 0.012(2) -0.010(2) C12 0.063(3) 0.070(3) 0.085(4) -0.034(3) 0.023(3) -0.013(3) C13 0.078(4) 0.104(5) 0.081(4) -0.053(4) 0.037(3) -0.040(4) C14 0.082(4) 0.101(5) 0.054(3) -0.019(3) 0.025(3) -0.051(4) C15 0.068(3) 0.068(3) 0.045(3) -0.007(2) 0.011(2) -0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.940(3) . ? Cu1 O1 2.043(3) . ? Cu1 N3 2.058(4) . ? Cu1 O4 2.076(3) . ? Cu1 N1 2.078(3) . ? Cu1 O2 2.721(3) . ? Cu1 O5 2.841(5) . ? Br2 C15 1.868(6) . ? Br2 Br1 5.3798(16) . ? Br1 C1 1.858(5) . ? O1 N4 1.272(4) . ? O2 N4 1.227(5) . ? O3 N4 1.228(4) . ? O4 N5 1.246(5) . ? O5 N5 1.197(6) . ? O6 N5 1.224(5) . ? N1 C1 1.325(6) . ? N1 C5 1.358(6) . ? N2 C10 1.329(5) . ? N2 C6 1.331(5) . ? N3 C15 1.336(6) . ? N3 C11 1.363(6) . ? C1 C2 1.381(7) . ? C2 C3 1.344(9) . ? C3 C4 1.375(9) . ? C4 C5 1.378(7) . ? C5 C6 1.459(7) . ? C6 C7 1.382(6) . ? C7 C8 1.361(8) . ? C8 C9 1.362(8) . ? C9 C10 1.385(6) . ? C10 C11 1.481(6) . ? C11 C12 1.383(6) . ? C12 C13 1.360(8) . ? C13 C14 1.377(9) . ? C14 C15 1.377(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 O1 134.47(13) . . ? N2 Cu1 N3 79.85(15) . . ? O1 Cu1 N3 97.49(14) . . ? N2 Cu1 O4 129.31(15) . . ? O1 Cu1 O4 96.21(14) . . ? N3 Cu1 O4 97.15(15) . . ? N2 Cu1 N1 79.75(15) . . ? O1 Cu1 N1 95.57(13) . . ? N3 Cu1 N1 159.53(15) . . ? O4 Cu1 N1 97.02(15) . . ? N2 Cu1 O2 83.69(12) . . ? O1 Cu1 O2 51.05(11) . . ? N3 Cu1 O2 95.13(13) . . ? O4 Cu1 O2 146.34(13) . . ? N1 Cu1 O2 80.98(13) . . ? N2 Cu1 O5 82.80(14) . . ? O1 Cu1 O5 141.84(12) . . ? N3 Cu1 O5 78.95(17) . . ? O4 Cu1 O5 47.61(14) . . ? N1 Cu1 O5 100.09(16) . . ? O2 Cu1 O5 166.02(13) . . ? C15 Br2 Br1 101.69(15) . . ? C1 Br1 Br2 100.52(15) . . ? N4 O1 Cu1 111.5(2) . . ? N4 O2 Cu1 79.5(2) . . ? N5 O4 Cu1 115.2(3) . . ? N5 O5 Cu1 77.8(3) . . ? C1 N1 C5 118.0(4) . . ? C1 N1 Cu1 129.6(3) . . ? C5 N1 Cu1 112.0(3) . . ? C10 N2 C6 121.9(4) . . ? C10 N2 Cu1 119.3(3) . . ? C6 N2 Cu1 118.8(3) . . ? C15 N3 C11 117.3(4) . . ? C15 N3 Cu1 129.5(3) . . ? C11 N3 Cu1 113.2(3) . . ? O2 N4 O3 123.0(4) . . ? O2 N4 O1 118.0(4) . . ? O3 N4 O1 119.0(4) . . ? O5 N5 O6 122.6(5) . . ? O5 N5 O4 118.9(4) . . ? O6 N5 O4 118.5(5) . . ? N1 C1 C2 123.5(5) . . ? N1 C1 Br1 118.8(4) . . ? C2 C1 Br1 117.7(4) . . ? C3 C2 C1 118.3(6) . . ? C2 C3 C4 120.0(5) . . ? C3 C4 C5 119.5(6) . . ? N1 C5 C4 120.8(5) . . ? N1 C5 C6 115.2(4) . . ? C4 C5 C6 124.0(5) . . ? N2 C6 C7 119.8(5) . . ? N2 C6 C5 113.8(4) . . ? C7 C6 C5 126.4(4) . . ? C8 C7 C6 118.8(5) . . ? C7 C8 C9 120.9(5) . . ? C8 C9 C10 118.5(5) . . ? N2 C10 C9 120.0(5) . . ? N2 C10 C11 113.2(4) . . ? C9 C10 C11 126.8(5) . . ? N3 C11 C12 122.2(5) . . ? N3 C11 C10 114.4(4) . . ? C12 C11 C10 123.4(5) . . ? C13 C12 C11 118.8(6) . . ? C12 C13 C14 120.1(5) . . ? C13 C14 C15 118.3(5) . . ? N3 C15 C14 123.2(5) . . ? N3 C15 Br2 118.1(4) . . ? C14 C15 Br2 118.7(4) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.733 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.082 # Attachment 'adroh1afinal1.cif' data_adroh1a _database_code_depnum_ccdc_archive 'CCDC 614031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Cu N4 O7' _chemical_formula_weight 427.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.612(2) _cell_length_b 18.431(4) _cell_length_c 10.852(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.820(5) _cell_angle_gamma 90.00 _cell_volume 1672.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 892 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 20.58 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; SADABS: Area-Detector Absorption Correction; Siemens Industrial Automation, Inc.: Madison, WI ; _exptl_special_details ; ; _diffrn_ambient_temperature 130(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker 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 8690 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2937 _reflns_number_gt 2276 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0380P)^2^+0.7430P] 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 2937 _refine_ls_number_parameters 268 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.083 _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 0.63006(7) 0.05880(3) 0.80235(5) 0.01638(18) Uani 1 1 d . . . O1 O 0.5064(4) 0.04863(19) 0.6254(3) 0.0200(8) Uani 1 1 d D . . H11O H 0.409(2) 0.040(3) 0.626(5) 0.039(17) Uiso 1 1 d D . . H12O H 0.507(6) 0.0810(19) 0.569(3) 0.032(16) Uiso 1 1 d D . . O2 O 0.7915(5) 0.1315(2) 0.7411(4) 0.0322(9) Uani 1 1 d D . . H21O H 0.819(7) 0.1759(11) 0.757(5) 0.048(19) Uiso 1 1 d D . . H22O H 0.839(5) 0.119(3) 0.683(3) 0.033(16) Uiso 1 1 d D . . O3 O 0.7896(4) -0.01007(17) 1.3589(3) 0.0202(8) Uani 1 1 d . . . N1 N 0.4986(4) 0.1352(2) 0.8634(3) 0.0171(9) Uani 1 1 d . . . N2 N 0.6906(4) 0.0398(2) 0.9819(3) 0.0161(9) Uani 1 1 d . . . N3 N 0.7687(4) -0.0304(2) 0.8047(3) 0.0168(9) Uani 1 1 d . . . C1 C 0.3988(6) 0.1825(3) 0.7916(4) 0.0210(11) Uani 1 1 d . . . H1 H 0.3849 0.1806 0.7040 0.025 Uiso 1 1 calc R . . C2 C 0.3152(6) 0.2340(3) 0.8424(5) 0.0261(12) Uani 1 1 d . . . H2 H 0.2454 0.2659 0.7902 0.031 Uiso 1 1 calc R . . C3 C 0.3383(6) 0.2369(3) 0.9730(5) 0.0265(12) Uani 1 1 d . . . H3 H 0.2847 0.2713 1.0100 0.032 Uiso 1 1 calc R . . C4 C 0.4409(5) 0.1886(3) 1.0475(4) 0.0201(11) Uani 1 1 d . . . H4 H 0.4578 0.1903 1.1353 0.024 Uiso 1 1 calc R . . C5 C 0.5189(5) 0.1375(3) 0.9914(4) 0.0170(10) Uani 1 1 d . . . C6 C 0.6279(5) 0.0803(2) 1.0608(4) 0.0152(10) Uani 1 1 d . . . C7 C 0.6593(5) 0.0663(3) 1.1893(4) 0.0189(11) Uani 1 1 d . . . H7 H 0.6146 0.0950 1.2424 0.023 Uiso 1 1 calc R . . C8 C 0.7613(5) 0.0071(3) 1.2393(4) 0.0206(11) Uani 1 1 d . . . C9 C 0.8267(5) -0.0341(3) 1.1531(4) 0.0177(11) Uani 1 1 d . . . H9 H 0.8956 -0.0726 1.1821 0.021 Uiso 1 1 calc R . . C10 C 0.7866(5) -0.0163(2) 1.0257(4) 0.0172(11) Uani 1 1 d . . . C11 C 0.8360(5) -0.0563(3) 0.9229(4) 0.0188(10) Uani 1 1 d . . . C12 C 0.9397(5) -0.1148(3) 0.9400(4) 0.0204(11) Uani 1 1 d . . . H12 H 0.9847 -0.1320 1.0212 0.024 Uiso 1 1 calc R . . C13 C 0.9762(6) -0.1475(3) 0.8360(4) 0.0247(12) Uani 1 1 d . . . H13 H 1.0445 -0.1873 0.8459 0.030 Uiso 1 1 calc R . . C14 C 0.9090(5) -0.1201(3) 0.7170(4) 0.0217(11) Uani 1 1 d . . . H14 H 0.9336 -0.1403 0.6455 0.026 Uiso 1 1 calc R . . C15 C 0.8051(5) -0.0624(3) 0.7054(4) 0.0203(11) Uani 1 1 d . . . H15 H 0.7584 -0.0450 0.6246 0.024 Uiso 1 1 calc R . . N4 N 0.4319(5) 0.2007(2) 0.4186(4) 0.0229(10) Uani 1 1 d . . . O4 O 0.5182(4) 0.14501(19) 0.4390(3) 0.0312(9) Uani 1 1 d . . . O5 O 0.3424(4) 0.2165(2) 0.4888(3) 0.0349(9) Uani 1 1 d . . . O6 O 0.4391(4) 0.24075(19) 0.3266(3) 0.0348(10) Uani 1 1 d . . . O7 O 0.9310(4) 0.0900(2) 0.5526(3) 0.0279(9) Uani 1 1 d D . . H71O H 1.016(4) 0.064(2) 0.573(5) 0.039(17) Uiso 1 1 d D . . H72O H 0.873(5) 0.064(2) 0.493(4) 0.043(18) Uiso 1 1 d 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 0.0188(3) 0.0175(3) 0.0119(3) 0.0006(3) 0.0016(2) 0.0007(3) O1 0.0207(19) 0.023(2) 0.0155(18) 0.0029(16) 0.0031(15) -0.0027(16) O2 0.045(2) 0.022(2) 0.038(2) -0.0099(19) 0.0254(19) -0.0145(19) O3 0.0205(18) 0.028(2) 0.0118(16) 0.0017(15) 0.0037(14) -0.0034(15) N1 0.015(2) 0.019(2) 0.019(2) 0.0009(18) 0.0049(17) 0.0014(18) N2 0.017(2) 0.016(2) 0.014(2) -0.0026(17) 0.0022(16) -0.0004(17) N3 0.016(2) 0.021(2) 0.014(2) 0.0019(18) 0.0056(16) -0.0010(17) C1 0.024(3) 0.023(3) 0.019(3) 0.003(2) 0.010(2) 0.004(2) C2 0.021(3) 0.022(3) 0.033(3) 0.009(2) 0.002(2) 0.005(2) C3 0.032(3) 0.017(3) 0.035(3) -0.005(2) 0.015(3) -0.001(2) C4 0.020(3) 0.020(3) 0.021(3) -0.004(2) 0.006(2) 0.001(2) C5 0.015(2) 0.022(3) 0.016(2) -0.004(2) 0.007(2) -0.006(2) C6 0.015(2) 0.016(3) 0.014(2) -0.004(2) 0.0037(19) -0.003(2) C7 0.021(2) 0.025(3) 0.012(2) -0.004(2) 0.0061(19) -0.006(2) C8 0.017(3) 0.024(3) 0.019(3) 0.002(2) 0.000(2) -0.009(2) C9 0.014(2) 0.023(3) 0.017(2) -0.001(2) 0.006(2) -0.001(2) C10 0.020(3) 0.014(3) 0.016(2) 0.001(2) 0.001(2) -0.003(2) C11 0.019(2) 0.014(2) 0.022(3) 0.000(2) 0.004(2) -0.008(2) C12 0.023(3) 0.019(3) 0.019(3) 0.006(2) 0.004(2) -0.001(2) C13 0.022(3) 0.020(3) 0.031(3) -0.002(2) 0.004(2) -0.001(2) C14 0.023(3) 0.024(3) 0.018(3) -0.006(2) 0.007(2) -0.003(2) C15 0.024(3) 0.023(3) 0.015(2) -0.003(2) 0.007(2) -0.005(2) N4 0.027(2) 0.023(3) 0.018(2) -0.004(2) 0.0033(19) -0.007(2) O4 0.039(2) 0.025(2) 0.029(2) 0.0090(17) 0.0066(17) 0.0018(18) O5 0.039(2) 0.044(2) 0.025(2) -0.0048(18) 0.0149(18) -0.0019(19) O6 0.054(3) 0.027(2) 0.029(2) 0.0161(18) 0.0218(19) 0.0157(19) O7 0.032(2) 0.028(2) 0.022(2) -0.0021(18) 0.0050(18) 0.0073(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 N2 1.924(4) . ? Cu1 O1 1.970(3) . ? Cu1 N1 2.016(4) . ? Cu1 N3 2.028(4) . ? Cu1 O2 2.147(4) . ? O3 C8 1.302(5) . ? N1 C1 1.335(6) . ? N1 C5 1.359(5) . ? N2 C10 1.339(5) . ? N2 C6 1.343(5) . ? N3 C15 1.329(5) . ? N3 C11 1.362(5) . ? C1 C2 1.383(6) . ? C2 C3 1.385(7) . ? C3 C4 1.373(6) . ? C4 C5 1.380(6) . ? C5 C6 1.490(6) . ? C6 C7 1.380(6) . ? C7 C8 1.425(6) . ? C8 C9 1.421(6) . ? C9 C10 1.383(6) . ? C10 C11 1.481(6) . ? C11 C12 1.385(6) . ? C12 C13 1.381(6) . ? C13 C14 1.378(6) . ? C14 C15 1.375(6) . ? N4 O5 1.241(5) . ? N4 O6 1.255(5) . ? N4 O4 1.255(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 O1 157.27(15) . . ? N2 Cu1 N1 80.33(15) . . ? O1 Cu1 N1 99.88(14) . . ? N2 Cu1 N3 79.86(15) . . ? O1 Cu1 N3 96.57(14) . . ? N1 Cu1 N3 159.64(14) . . ? N2 Cu1 O2 112.79(15) . . ? O1 Cu1 O2 89.82(15) . . ? N1 Cu1 O2 96.99(15) . . ? N3 Cu1 O2 94.96(15) . . ? C1 N1 C5 119.0(4) . . ? C1 N1 Cu1 126.7(3) . . ? C5 N1 Cu1 114.3(3) . . ? C10 N2 C6 120.7(4) . . ? C10 N2 Cu1 119.7(3) . . ? C6 N2 Cu1 119.5(3) . . ? C15 N3 C11 118.6(4) . . ? C15 N3 Cu1 127.0(3) . . ? C11 N3 Cu1 114.3(3) . . ? N1 C1 C2 122.6(4) . . ? C1 C2 C3 118.3(5) . . ? C4 C3 C2 119.5(5) . . ? C3 C4 C5 119.7(4) . . ? N1 C5 C4 120.9(4) . . ? N1 C5 C6 114.0(4) . . ? C4 C5 C6 125.0(4) . . ? N2 C6 C7 122.0(4) . . ? N2 C6 C5 111.8(4) . . ? C7 C6 C5 126.2(4) . . ? C6 C7 C8 118.8(4) . . ? O3 C8 C9 121.1(4) . . ? O3 C8 C7 121.1(4) . . ? C9 C8 C7 117.7(4) . . ? C10 C9 C8 119.2(4) . . ? N2 C10 C9 121.6(4) . . ? N2 C10 C11 112.4(4) . . ? C9 C10 C11 125.9(4) . . ? N3 C11 C12 121.0(4) . . ? N3 C11 C10 113.6(4) . . ? C12 C11 C10 125.4(4) . . ? C13 C12 C11 119.8(4) . . ? C14 C13 C12 118.6(5) . . ? C15 C14 C13 119.2(4) . . ? N3 C15 C14 122.9(4) . . ? O5 N4 O6 120.4(4) . . ? O5 N4 O4 120.8(4) . . ? O6 N4 O4 118.8(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.454 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.096