# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mario.wriedt@chem.tamu.edu _publ_contact_author_name 'Mario Wriedt' loop_ _publ_author_name 'Mario Wriedt' 'Hong-Cai Zhou' data_mw18 _database_code_depnum_ccdc_archive 'CCDC 847988' #TrackingRef 'compound_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C4 H6 Cu N5 O4, H2 O' _chemical_formula_sum 'C4 H8 Cu N5 O5' _chemical_formula_weight 269.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 7.639(2) _cell_length_b 8.088(2) _cell_length_c 8.169(2) _cell_angle_alpha 67.860(3) _cell_angle_beta 71.560(3) _cell_angle_gamma 84.827(3) _cell_volume 443.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3633 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 26.73 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 2.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_T_max 0.798 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3633 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0235 _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 -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.73 _reflns_number_total 1861 _reflns_number_gt 1733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2 (Bruker, 2008)' _computing_data_reduction 'APEX2 (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 2008)' _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^)+(0.0344P)^2^+0.4469P] 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 1861 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.69779(4) 0.64197(3) 0.26151(3) 0.01023(10) Uani 1 1 d . . . N1 N 0.4673(2) 0.5777(2) 0.6448(3) 0.0102(4) Uani 1 1 d . . . N2 N 0.5990(3) 0.6832(2) 0.4996(3) 0.0105(4) Uani 1 1 d . . . N3 N 0.6429(3) 0.8137(3) 0.5419(3) 0.0156(4) Uani 1 1 d . . . N4 N 0.5400(3) 0.7946(3) 0.7147(3) 0.0155(4) Uani 1 1 d . . . C1 C 0.2911(3) 0.5594(3) 0.9543(3) 0.0118(4) Uani 1 1 d . . . C2 C 0.4346(3) 0.6496(3) 0.7728(3) 0.0115(4) Uani 1 1 d . . . O1 O 0.2547(2) 0.6188(2) 1.0798(2) 0.0154(3) Uani 1 1 d . . . O2 O 0.2152(2) 0.4222(2) 0.9617(2) 0.0136(3) Uani 1 1 d . . . N11 N 0.8739(3) 0.8581(2) 0.1124(3) 0.0112(4) Uani 1 1 d . . . C11 C 0.9806(3) 0.9190(3) 0.1808(3) 0.0123(4) Uani 1 1 d . . . H11 H 0.9699 0.8640 0.3090 0.015 Uiso 1 1 calc R . . C12 C 0.8938(3) 0.9397(3) -0.0696(3) 0.0116(4) Uani 1 1 d . . . H12 H 0.8203 0.8998 -0.1229 0.014 Uiso 1 1 calc R . . O1W O 0.4646(2) 0.8311(2) 0.1475(2) 0.0149(3) Uani 1 1 d . . . H1A H 0.3970 0.7743 0.1218 0.022 Uiso 0.67 1 d PR . . H1B H 0.4024 0.8522 0.2422 0.022 Uiso 0.67 1 d PR . . H1C H 0.4944 0.9257 0.0534 0.022 Uiso 0.67 1 d PR . . O2W O 0.9414(2) 0.4751(2) 0.3659(2) 0.0143(3) Uani 1 1 d . . . H2A H 1.0339 0.5035 0.2705 0.021 Uiso 0.67 1 d PR . . H2B H 0.9848 0.5007 0.4363 0.021 Uiso 0.67 1 d PR . . H2C H 0.9230 0.3681 0.3833 0.021 Uiso 0.67 1 d PR . . O3W O 0.7991(3) 0.1324(2) 0.5402(3) 0.0211(4) Uani 1 1 d . . . H3A H 0.7737 0.0574 0.5020 0.032 Uiso 0.67 1 d PR . . H3B H 0.6957 0.1302 0.6180 0.032 Uiso 0.67 1 d PR . . H3C H 0.8286 0.2298 0.4496 0.032 Uiso 0.67 1 d PR . . 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 0.01163(16) 0.00957(15) 0.00810(15) -0.00311(11) -0.00003(11) -0.00451(10) N1 0.0093(9) 0.0100(9) 0.0099(9) -0.0028(7) -0.0014(7) -0.0024(7) N2 0.0107(9) 0.0096(9) 0.0095(9) -0.0025(7) -0.0014(7) -0.0027(7) N3 0.0183(10) 0.0145(10) 0.0129(9) -0.0067(8) 0.0003(8) -0.0059(8) N4 0.0171(10) 0.0165(10) 0.0116(9) -0.0066(8) 0.0009(8) -0.0059(8) C1 0.0105(10) 0.0124(10) 0.0118(11) -0.0031(9) -0.0043(9) 0.0004(8) C2 0.0110(10) 0.0110(10) 0.0130(11) -0.0044(9) -0.0043(9) 0.0007(8) O1 0.0161(8) 0.0170(8) 0.0127(8) -0.0083(7) 0.0009(6) -0.0048(7) O2 0.0154(8) 0.0133(8) 0.0108(8) -0.0045(6) -0.0007(6) -0.0048(6) N11 0.0112(9) 0.0090(9) 0.0127(9) -0.0038(7) -0.0031(7) -0.0001(7) C11 0.0128(10) 0.0132(11) 0.0105(10) -0.0043(9) -0.0029(9) -0.0005(9) C12 0.0114(10) 0.0107(10) 0.0131(11) -0.0046(9) -0.0039(8) -0.0005(8) O1W 0.0163(8) 0.0144(8) 0.0153(8) -0.0057(7) -0.0059(7) -0.0004(7) O2W 0.0134(8) 0.0156(8) 0.0130(8) -0.0052(7) -0.0023(6) -0.0020(6) O3W 0.0240(9) 0.0168(9) 0.0242(9) -0.0082(7) -0.0078(8) -0.0029(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.9799(16) 2_666 ? Cu1 N2 1.9943(19) . ? Cu1 N1 2.0254(19) 2_666 ? Cu1 N11 2.0323(19) . ? Cu1 O2W 2.3865(17) . ? Cu1 O1W 2.4213(17) . ? N1 C2 1.327(3) . ? N1 N2 1.336(3) . ? N1 Cu1 2.0254(19) 2_666 ? N2 N3 1.326(3) . ? N3 N4 1.338(3) . ? N4 C2 1.326(3) . ? C1 O1 1.236(3) . ? C1 O2 1.271(3) . ? C1 C2 1.494(3) . ? O2 Cu1 1.9799(16) 2_666 ? N11 C11 1.337(3) . ? N11 C12 1.343(3) . ? C11 C12 1.384(3) 2_775 ? C12 C11 1.384(3) 2_775 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 N2 174.52(7) 2_666 . ? O2 Cu1 N1 81.39(7) 2_666 2_666 ? N2 Cu1 N1 93.33(7) . 2_666 ? O2 Cu1 N11 86.37(7) 2_666 . ? N2 Cu1 N11 98.99(8) . . ? N1 Cu1 N11 167.40(7) 2_666 . ? O2 Cu1 O2W 89.00(6) 2_666 . ? N2 Cu1 O2W 89.87(7) . . ? N1 Cu1 O2W 93.45(7) 2_666 . ? N11 Cu1 O2W 89.27(7) . . ? O2 Cu1 O1W 91.71(6) 2_666 . ? N2 Cu1 O1W 89.80(7) . . ? N1 Cu1 O1W 90.78(7) 2_666 . ? N11 Cu1 O1W 86.61(7) . . ? O2W Cu1 O1W 175.77(5) . . ? C2 N1 N2 105.03(18) . . ? C2 N1 Cu1 110.79(15) . 2_666 ? N2 N1 Cu1 144.17(15) . 2_666 ? N3 N2 N1 108.86(17) . . ? N3 N2 Cu1 128.62(15) . . ? N1 N2 Cu1 122.50(14) . . ? N2 N3 N4 109.33(18) . . ? C2 N4 N3 104.66(19) . . ? O1 C1 O2 125.8(2) . . ? O1 C1 C2 120.8(2) . . ? O2 C1 C2 113.38(19) . . ? N4 C2 N1 112.1(2) . . ? N4 C2 C1 130.3(2) . . ? N1 C2 C1 117.5(2) . . ? C1 O2 Cu1 116.90(14) . 2_666 ? C11 N11 C12 117.1(2) . . ? C11 N11 Cu1 124.29(16) . . ? C12 N11 Cu1 118.45(15) . . ? N11 C11 C12 121.7(2) . 2_775 ? N11 C12 C11 121.2(2) . 2_775 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.500 _refine_diff_density_min -0.619 _refine_diff_density_rms 0.081 # Attachment 'compound_2.cif' data_mw20neu _database_code_depnum_ccdc_archive 'CCDC 847989' #TrackingRef 'compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Cu N6 O2' _chemical_formula_sum 'C6 H4 Cu N6 O2' _chemical_formula_weight 255.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/m' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 5.606(3) _cell_length_b 6.830(4) _cell_length_c 11.891(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.379(7) _cell_angle_gamma 90.00 _cell_volume 449.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4077 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 28.51 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_f_000 254 _exptl_absorpt_coefficient_mu 2.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_t_min 0.690 _exptl_absorpt_correction_t_max 0.827 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4077 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 28.51 _reflns_number_total 1215 _reflns_number_gt 1024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2 (Bruker, 2008)' _computing_data_reduction 'APEX2 (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 2008)' _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^)+(0.0321P)^2^+1.7952P] 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 1215 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.61701(10) 0.2500 0.75913(5) 0.01025(18) Uani 1 2 d S . . N1 N 0.2456(7) 0.2500 0.6321(4) 0.0142(8) Uani 1 2 d S . . N2 N 0.0970(7) 0.2500 0.5299(4) 0.0150(9) Uani 1 2 d S . . N3 N -0.1303(7) 0.2500 0.5463(3) 0.0143(8) Uani 1 2 d S . . N4 N -0.1335(7) 0.2500 0.6592(3) 0.0119(8) Uani 1 2 d S . . C1 C 0.1720(9) 0.2500 0.8356(4) 0.0141(10) Uani 1 2 d S . . C2 C 0.0965(8) 0.2500 0.7090(4) 0.0128(9) Uani 1 2 d S . . O1 O 0.3965(6) 0.2500 0.8737(3) 0.0141(7) Uani 1 2 d S . . O2 O 0.0052(6) 0.2500 0.8942(3) 0.0151(7) Uani 1 2 d S . . N11 N 0.6197(5) 0.5478(4) 0.7630(2) 0.0122(5) Uani 1 1 d . . . C11 C 0.5615(7) 0.6484(5) 0.6670(3) 0.0191(8) Uani 1 1 d . . . H11 H 0.5191 0.5801 0.5970 0.023 Uiso 1 1 calc R . . C12 C 0.6774(8) 0.6482(6) 0.8597(3) 0.0254(9) Uani 1 1 d . . . H12 H 0.7192 0.5796 0.9297 0.030 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 0.0096(3) 0.0072(3) 0.0145(3) 0.000 0.0035(2) 0.000 N1 0.0147(19) 0.013(2) 0.014(2) 0.000 -0.0003(15) 0.000 N2 0.0174(19) 0.016(2) 0.013(2) 0.000 0.0069(16) 0.000 N3 0.0160(19) 0.015(2) 0.013(2) 0.000 0.0055(16) 0.000 N4 0.0140(18) 0.011(2) 0.0107(19) 0.000 0.0024(15) 0.000 C1 0.018(2) 0.006(2) 0.020(3) 0.000 0.0072(19) 0.000 C2 0.014(2) 0.009(2) 0.016(2) 0.000 0.0031(18) 0.000 O1 0.0126(15) 0.0140(18) 0.0159(18) 0.000 0.0031(13) 0.000 O2 0.0161(16) 0.0181(19) 0.0131(17) 0.000 0.0085(13) 0.000 N11 0.0121(12) 0.0107(13) 0.0143(13) -0.0001(12) 0.0040(10) -0.0008(11) C11 0.0328(19) 0.0125(19) 0.0113(16) -0.0009(14) 0.0018(14) -0.0003(15) C12 0.046(2) 0.012(2) 0.0160(18) -0.0002(15) -0.0034(16) 0.0016(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.977(4) 1_655 ? Cu1 O1 1.983(4) . ? Cu1 N11 2.034(3) . ? Cu1 N11 2.034(3) 4_565 ? Cu1 N1 2.364(4) . ? N1 C2 1.335(6) . ? N1 N2 1.357(6) . ? N2 N3 1.320(6) . ? N3 N4 1.346(6) . ? N4 C2 1.328(6) . ? N4 Cu1 1.977(4) 1_455 ? C1 O2 1.254(6) . ? C1 O1 1.266(6) . ? C1 C2 1.496(7) . ? N11 C11 1.327(4) . ? N11 C12 1.332(5) . ? C11 C11 1.388(7) 4_575 ? C12 C12 1.391(8) 4_575 ? 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 N4 Cu1 O1 173.68(15) 1_655 . ? N4 Cu1 N11 90.59(8) 1_655 . ? O1 Cu1 N11 89.28(8) . . ? N4 Cu1 N11 90.59(8) 1_655 4_565 ? O1 Cu1 N11 89.29(8) . 4_565 ? N11 Cu1 N11 177.38(17) . 4_565 ? N4 Cu1 N1 104.59(16) 1_655 . ? O1 Cu1 N1 81.73(15) . . ? N11 Cu1 N1 90.98(8) . . ? N11 Cu1 N1 90.98(8) 4_565 . ? C2 N1 N2 104.6(4) . . ? C2 N1 Cu1 98.4(3) . . ? N2 N1 Cu1 157.0(3) . . ? N3 N2 N1 109.5(4) . . ? N2 N3 N4 108.5(4) . . ? C2 N4 N3 105.9(4) . . ? C2 N4 Cu1 117.6(3) . 1_455 ? N3 N4 Cu1 136.5(3) . 1_455 ? O2 C1 O1 126.1(5) . . ? O2 C1 C2 116.4(4) . . ? O1 C1 C2 117.5(4) . . ? N4 C2 N1 111.4(4) . . ? N4 C2 C1 122.9(4) . . ? N1 C2 C1 125.7(4) . . ? C1 O1 Cu1 116.7(3) . . ? C11 N11 C12 117.8(3) . . ? C11 N11 Cu1 119.9(2) . . ? C12 N11 Cu1 122.3(2) . . ? N11 C11 C11 121.2(2) . 4_575 ? N11 C12 C12 121.0(2) . 4_575 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.692 _refine_diff_density_min -0.671 _refine_diff_density_rms 0.139 # Attachment 'compound_3.cif' data_mw249 _database_code_depnum_ccdc_archive 'CCDC 847990' #TrackingRef 'compound_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 Cu N6 O3' _chemical_formula_sum 'C6 H6 Cu N6 O3' _chemical_formula_weight 273.71 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 'P 21/n' _space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.272(3) _cell_length_b 6.864(3) _cell_length_c 14.484(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.052(4) _cell_angle_gamma 90.00 _cell_volume 919.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8311 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 25.99 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.715 _exptl_absorpt_correction_T_max 0.767 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6881 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1817 _reflns_number_gt 1663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2 (Bruker, 2008)' _computing_data_reduction 'APEX2 (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 2008)' _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^)+(0.0234P)^2^+0.8815P] 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 1817 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0549 _refine_ls_wR_factor_gt 0.0538 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.47213(2) 0.51187(3) 0.359172(14) 0.00940(9) Uani 1 1 d . . . N1 N 0.67804(17) 0.9553(2) 0.49430(11) 0.0134(3) Uani 1 1 d . . . N2 N 0.65954(17) 0.8589(2) 0.57332(11) 0.0140(3) Uani 1 1 d . . . N3 N 0.58348(16) 0.6980(2) 0.55372(10) 0.0104(3) Uani 1 1 d . . . N4 N 0.55159(16) 0.6880(2) 0.46249(10) 0.0098(3) Uani 1 1 d . . . C1 C 0.61040(19) 0.8468(3) 0.42811(13) 0.0105(4) Uani 1 1 d . . . C2 C 0.59797(18) 0.8745(3) 0.32534(12) 0.0106(4) Uani 1 1 d . . . O1 O 0.53549(14) 0.73340(18) 0.28153(9) 0.0125(3) Uani 1 1 d . . . O2 O 0.64897(14) 1.02136(18) 0.29024(9) 0.0133(3) Uani 1 1 d . . . N11 N 0.24066(17) 0.6623(2) 0.35261(11) 0.0127(3) Uani 1 1 d . . . N12 N 0.08098(16) 0.8671(2) 0.26104(10) 0.0108(3) Uani 1 1 d . . . C11 C 0.20157(19) 0.7609(3) 0.27563(12) 0.0113(4) Uani 1 1 d . . . H11A H 0.2648 0.7554 0.2269 0.014 Uiso 1 1 calc R . . C12 C -0.00712(19) 0.8776(3) 0.33112(13) 0.0131(4) Uani 1 1 d . . . H12A H -0.0932 0.9528 0.3236 0.016 Uiso 1 1 calc R . . C13 C 0.0255(2) 0.7815(3) 0.41343(13) 0.0157(4) Uani 1 1 d . . . H13A H -0.0366 0.7888 0.4627 0.019 Uiso 1 1 calc R . . C14 C 0.1524(2) 0.6734(3) 0.42182(13) 0.0151(4) Uani 1 1 d . . . H14A H 0.1772 0.6059 0.4779 0.018 Uiso 1 1 calc R . . O1W O 0.71597(14) 0.38930(19) 0.36637(9) 0.0143(3) Uani 1 1 d . . . H1W H 0.7638 0.4292 0.3230 0.021 Uiso 1 1 d R . . H2W H 0.7049 0.2740 0.3478 0.021 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01203(13) 0.00894(13) 0.00698(13) -0.00004(8) -0.00098(9) -0.00217(8) N1 0.0158(8) 0.0137(8) 0.0106(8) 0.0006(6) -0.0002(6) -0.0029(6) N2 0.0166(8) 0.0121(8) 0.0131(8) 0.0006(6) -0.0006(6) -0.0042(6) N3 0.0111(7) 0.0113(7) 0.0084(8) -0.0013(6) -0.0017(6) -0.0001(6) N4 0.0106(7) 0.0101(7) 0.0085(7) 0.0004(6) -0.0001(6) 0.0009(6) C1 0.0093(8) 0.0096(8) 0.0124(9) -0.0009(7) 0.0007(7) 0.0017(7) C2 0.0086(8) 0.0122(9) 0.0110(9) 0.0000(7) 0.0012(7) 0.0030(7) O1 0.0156(6) 0.0121(6) 0.0097(6) 0.0002(5) -0.0001(5) -0.0021(5) O2 0.0168(7) 0.0108(6) 0.0124(7) 0.0017(5) 0.0027(5) -0.0014(5) N11 0.0144(8) 0.0130(7) 0.0104(8) -0.0003(6) -0.0019(6) 0.0013(6) N12 0.0115(7) 0.0108(7) 0.0096(8) 0.0002(6) -0.0019(6) -0.0005(6) C11 0.0117(8) 0.0126(8) 0.0093(9) -0.0007(7) -0.0010(7) -0.0003(7) C12 0.0097(8) 0.0148(9) 0.0147(9) -0.0003(7) 0.0003(7) 0.0008(7) C13 0.0155(9) 0.0210(10) 0.0109(9) 0.0005(7) 0.0028(7) 0.0002(8) C14 0.0175(9) 0.0172(9) 0.0102(9) 0.0026(7) -0.0019(7) -0.0010(8) O1W 0.0177(7) 0.0137(6) 0.0120(7) -0.0003(5) 0.0039(5) 0.0000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 2.0038(14) . ? Cu1 N3 2.0063(16) 3_666 ? Cu1 N4 2.0219(16) . ? Cu1 N12 2.0349(16) 2_545 ? Cu1 N11 2.3774(17) . ? Cu1 O1W 2.4076(15) . ? N1 C1 1.335(2) . ? N1 N2 1.343(2) . ? N2 N3 1.330(2) . ? N3 N4 1.335(2) . ? N3 Cu1 2.0063(16) 3_666 ? N4 C1 1.331(2) . ? C1 C2 1.497(3) . ? C2 O2 1.238(2) . ? C2 O1 1.274(2) . ? N11 C11 1.333(2) . ? N11 C14 1.340(2) . ? N12 C11 1.339(2) . ? N12 C12 1.349(2) . ? N12 Cu1 2.0349(16) 2 ? C12 C13 1.378(3) . ? C13 C14 1.389(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 O1 Cu1 N3 175.14(6) . 3_666 ? O1 Cu1 N4 81.70(6) . . ? N3 Cu1 N4 93.46(7) 3_666 . ? O1 Cu1 N12 87.32(6) . 2_545 ? N3 Cu1 N12 97.47(7) 3_666 2_545 ? N4 Cu1 N12 168.19(6) . 2_545 ? O1 Cu1 N11 87.00(6) . . ? N3 Cu1 N11 93.76(6) 3_666 . ? N4 Cu1 N11 92.90(6) . . ? N12 Cu1 N11 90.84(6) 2_545 . ? O1 Cu1 O1W 88.73(5) . . ? N3 Cu1 O1W 90.24(5) 3_666 . ? N4 Cu1 O1W 83.39(5) . . ? N12 Cu1 O1W 92.07(5) 2_545 . ? N11 Cu1 O1W 174.71(5) . . ? C1 N1 N2 104.82(15) . . ? N3 N2 N1 108.93(15) . . ? N2 N3 N4 109.33(14) . . ? N2 N3 Cu1 128.16(12) . 3_666 ? N4 N3 Cu1 122.46(11) . 3_666 ? C1 N4 N3 105.08(15) . . ? C1 N4 Cu1 110.50(12) . . ? N3 N4 Cu1 143.79(12) . . ? N4 C1 N1 111.84(16) . . ? N4 C1 C2 118.10(16) . . ? N1 C1 C2 130.00(17) . . ? O2 C2 O1 126.00(17) . . ? O2 C2 C1 120.46(16) . . ? O1 C2 C1 113.52(16) . . ? C2 O1 Cu1 115.99(12) . . ? C11 N11 C14 116.90(16) . . ? C11 N11 Cu1 116.45(12) . . ? C14 N11 Cu1 126.30(12) . . ? C11 N12 C12 116.99(16) . . ? C11 N12 Cu1 123.36(13) . 2 ? C12 N12 Cu1 119.65(12) . 2 ? N11 C11 N12 125.68(17) . . ? N12 C12 C13 121.18(17) . . ? C12 C13 C14 117.67(17) . . ? N11 C14 C13 121.56(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.358 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.063 # Attachment 'compound_4.cif' data_mw65 _database_code_depnum_ccdc_archive 'CCDC 847991' #TrackingRef 'compound_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 Cu N5 O3' _chemical_formula_sum 'C8 H7 Cu N5 O3' _chemical_formula_weight 284.73 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 'P 21/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 7.5502(19) _cell_length_b 12.884(3) _cell_length_c 10.036(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.038(3) _cell_angle_gamma 90.00 _cell_volume 966.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11532 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.50 _exptl_crystal_description clock _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 2.264 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.727 _exptl_absorpt_correction_T_max 0.812 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11532 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28.50 _reflns_number_total 2414 _reflns_number_gt 2071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2 (Bruker, 2008)' _computing_data_reduction 'APEX2 (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 2008)' _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^)+(0.0339P)^2^+0.5870P] 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 2414 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.20176(3) 0.554369(18) 0.63487(2) 0.01253(9) Uani 1 1 d . . . O1 O 0.18756(19) 0.67975(11) 0.74700(14) 0.0173(3) Uani 1 1 d . . . O2 O 0.0206(2) 0.81974(11) 0.77350(15) 0.0205(3) Uani 1 1 d . . . C1 C 0.0488(3) 0.73735(16) 0.7188(2) 0.0152(4) Uani 1 1 d . . . C2 C -0.0845(3) 0.69193(15) 0.6101(2) 0.0135(4) Uani 1 1 d . . . N1 N -0.0446(2) 0.60091(13) 0.55948(16) 0.0132(3) Uani 1 1 d . . . N2 N -0.1863(2) 0.57649(13) 0.47009(17) 0.0136(3) Uani 1 1 d . . . N3 N -0.3077(2) 0.65054(13) 0.46841(17) 0.0152(3) Uani 1 1 d . . . N4 N -0.2464(2) 0.72471(13) 0.55710(17) 0.0156(3) Uani 1 1 d . . . N11 N 0.4261(2) 0.51918(13) 0.75291(16) 0.0133(3) Uani 1 1 d . . . C16 C 0.9309(3) 0.46703(16) 0.9927(2) 0.0162(4) Uani 1 1 d . . . H16A H 0.9465 0.4023 1.0381 0.019 Uiso 1 1 calc R . . C11 C 0.4620(3) 0.42904(15) 0.8181(2) 0.0147(4) Uani 1 1 d . . . H11A H 0.3735 0.3761 0.8095 0.018 Uiso 1 1 calc R . . C12 C 0.6245(3) 0.41074(16) 0.8978(2) 0.0154(4) Uani 1 1 d . . . H12A H 0.6458 0.3462 0.9429 0.018 Uiso 1 1 calc R . . C13 C 0.7569(3) 0.48734(16) 0.91165(19) 0.0143(4) Uani 1 1 d . . . C14 C 0.7150(3) 0.58178(16) 0.8466(2) 0.0154(4) Uani 1 1 d . . . H14A H 0.7995 0.6368 0.8555 0.018 Uiso 1 1 calc R . . C15 C 0.5508(3) 0.59500(16) 0.7695(2) 0.0147(4) Uani 1 1 d . . . H15A H 0.5242 0.6599 0.7264 0.018 Uiso 1 1 calc R . . O1W O 0.30892(19) 0.64331(12) 0.47462(15) 0.0208(3) Uani 1 1 d . . . H1O1 H 0.4045 0.6442 0.4450 0.031 Uiso 1 1 d R . . H2O1 H 0.2363 0.6621 0.4054 0.031 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00865(13) 0.01361(14) 0.01412(14) -0.00141(9) -0.00262(9) 0.00066(9) O1 0.0135(7) 0.0189(7) 0.0178(7) -0.0047(6) -0.0040(5) 0.0012(6) O2 0.0184(8) 0.0201(8) 0.0215(8) -0.0080(6) -0.0021(6) 0.0030(6) C1 0.0110(9) 0.0184(10) 0.0159(9) -0.0004(8) 0.0011(7) -0.0022(7) C2 0.0112(9) 0.0145(9) 0.0145(9) 0.0003(7) 0.0012(7) 0.0003(7) N1 0.0103(8) 0.0148(8) 0.0135(8) -0.0010(7) -0.0015(6) -0.0005(6) N2 0.0087(8) 0.0170(8) 0.0141(8) 0.0000(7) -0.0021(6) 0.0008(6) N3 0.0122(8) 0.0142(8) 0.0184(8) -0.0010(7) -0.0007(7) 0.0029(6) N4 0.0132(8) 0.0166(8) 0.0164(8) -0.0018(7) -0.0005(6) 0.0007(7) N11 0.0113(8) 0.0148(8) 0.0130(8) -0.0005(6) -0.0009(6) 0.0005(6) C16 0.0144(10) 0.0180(10) 0.0150(9) 0.0023(8) -0.0021(8) 0.0030(8) C11 0.0128(10) 0.0155(9) 0.0155(9) 0.0002(8) 0.0005(7) -0.0009(7) C12 0.0150(10) 0.0164(9) 0.0143(9) 0.0034(8) 0.0002(7) 0.0005(8) C13 0.0116(9) 0.0184(10) 0.0122(9) -0.0020(8) -0.0010(7) 0.0016(7) C14 0.0106(10) 0.0180(10) 0.0167(10) -0.0012(8) -0.0008(7) -0.0029(7) C15 0.0125(10) 0.0156(9) 0.0152(9) 0.0019(8) -0.0007(7) -0.0001(7) O1W 0.0124(7) 0.0297(8) 0.0192(8) 0.0085(6) -0.0010(6) 0.0006(6) _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 N11 1.9789(17) . ? Cu1 O1 1.9802(15) . ? Cu1 N2 1.9828(17) 3_566 ? Cu1 N1 1.9998(17) . ? Cu1 O1W 2.2177(15) . ? O1 C1 1.283(2) . ? O2 C1 1.227(2) . ? C1 C2 1.496(3) . ? C2 N1 1.329(3) . ? C2 N4 1.331(3) . ? N1 N2 1.334(2) . ? N2 N3 1.322(2) . ? N2 Cu1 1.9827(17) 3_566 ? N3 N4 1.343(2) . ? N11 C11 1.342(3) . ? N11 C15 1.351(3) . ? C16 C16 1.337(4) 3_767 ? C16 C13 1.469(3) . ? C11 C12 1.388(3) . ? C12 C13 1.398(3) . ? C13 C14 1.396(3) . ? C14 C15 1.377(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 N11 Cu1 O1 87.50(6) . . ? N11 Cu1 N2 96.04(7) . 3_566 ? O1 Cu1 N2 172.63(7) . 3_566 ? N11 Cu1 N1 165.50(7) . . ? O1 Cu1 N1 81.31(6) . . ? N2 Cu1 N1 94.09(7) 3_566 . ? N11 Cu1 O1W 100.61(6) . . ? O1 Cu1 O1W 92.57(6) . . ? N2 Cu1 O1W 93.13(7) 3_566 . ? N1 Cu1 O1W 89.15(6) . . ? C1 O1 Cu1 117.00(13) . . ? O2 C1 O1 126.10(19) . . ? O2 C1 C2 121.55(18) . . ? O1 C1 C2 112.33(17) . . ? N1 C2 N4 111.80(17) . . ? N1 C2 C1 117.29(17) . . ? N4 C2 C1 130.81(18) . . ? C2 N1 N2 105.19(16) . . ? C2 N1 Cu1 111.62(13) . . ? N2 N1 Cu1 143.09(13) . . ? N3 N2 N1 109.14(15) . . ? N3 N2 Cu1 128.14(13) . 3_566 ? N1 N2 Cu1 122.69(13) . 3_566 ? N2 N3 N4 109.30(15) . . ? C2 N4 N3 104.56(16) . . ? C11 N11 C15 118.40(17) . . ? C11 N11 Cu1 126.02(14) . . ? C15 N11 Cu1 115.57(13) . . ? C16 C16 C13 124.8(2) 3_767 . ? N11 C11 C12 122.02(18) . . ? C11 C12 C13 119.99(19) . . ? C14 C13 C12 117.16(18) . . ? C14 C13 C16 122.76(19) . . ? C12 C13 C16 120.08(19) . . ? C15 C14 C13 119.87(19) . . ? N11 C15 C14 122.49(19) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.459 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.079 # Attachment 'compound_5.cif' data_mw242w _database_code_depnum_ccdc_archive 'CCDC 847992' #TrackingRef 'compound_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 Cu N6 O3' _chemical_formula_sum 'C7 H6 Cu N6 O3' _chemical_formula_weight 285.72 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 'P 21/c' _space_group_name_Hall '-P 2ybc' 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 7.633(6) _cell_length_b 12.718(9) _cell_length_c 10.105(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.016(8) _cell_angle_gamma 90.00 _cell_volume 963.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11113 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.40 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.971 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 2.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10832 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 28.40 _reflns_number_total 2371 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_cell_refinement 'APEX2 (Bruker, 2008)' _computing_data_reduction 'APEX2 (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 2008)' _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^)+(0.0518P)^2^+0.8129P] 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 2371 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.20952(5) 0.55719(3) 0.63544(4) 0.02250(14) Uani 1 1 d . . . O1 O 0.2039(3) 0.68772(18) 0.7422(2) 0.0278(5) Uani 1 1 d . . . O2 O 0.0337(3) 0.82763(18) 0.7684(2) 0.0312(5) Uani 1 1 d . . . C1 C 0.0610(4) 0.7434(3) 0.7152(3) 0.0255(7) Uani 1 1 d . . . C2 C -0.0786(4) 0.6955(2) 0.6069(3) 0.0225(6) Uani 1 1 d . . . N1 N -0.0388(3) 0.6040(2) 0.5557(3) 0.0230(5) Uani 1 1 d . . . N2 N -0.1858(4) 0.5781(2) 0.4657(3) 0.0239(6) Uani 1 1 d . . . N3 N -0.3086(4) 0.6515(2) 0.4643(3) 0.0251(6) Uani 1 1 d . . . N4 N -0.2441(4) 0.7271(2) 0.5548(3) 0.0256(6) Uani 1 1 d . . . N11 N 0.4393(4) 0.5212(2) 0.7578(3) 0.0234(6) Uani 1 1 d . . . N12 N 0.9415(4) 0.4665(2) 1.0044(3) 0.0281(6) Uani 1 1 d . . . C11 C 0.4747(4) 0.4312(2) 0.8274(3) 0.0242(7) Uani 1 1 d . . . H11A H 0.3845 0.3789 0.8195 0.029 Uiso 1 1 calc R . . C12 C 0.6401(4) 0.4119(3) 0.9114(3) 0.0251(7) Uani 1 1 d . . . H12A H 0.6616 0.3485 0.9614 0.030 Uiso 1 1 calc R . . C13 C 0.7718(4) 0.4886(3) 0.9194(3) 0.0236(6) Uani 1 1 d . . . C14 C 0.7333(4) 0.5827(3) 0.8486(3) 0.0246(7) Uani 1 1 d . . . H14A H 0.8206 0.6366 0.8546 0.029 Uiso 1 1 calc R . . C15 C 0.5668(4) 0.5959(3) 0.7701(3) 0.0243(7) Uani 1 1 d . . . H15A H 0.5405 0.6602 0.7225 0.029 Uiso 1 1 calc R . . O1W O 0.3180(3) 0.6369(2) 0.4752(2) 0.0334(6) Uani 1 1 d . . . H1O1 H 0.4137 0.6377 0.4456 0.050 Uiso 1 1 d R . . H2O1 H 0.2454 0.6556 0.4060 0.050 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0223(2) 0.0215(2) 0.0210(2) -0.00164(15) -0.00249(14) 0.00073(15) O1 0.0275(12) 0.0270(12) 0.0255(11) -0.0047(9) -0.0037(9) 0.0019(9) O2 0.0340(13) 0.0279(12) 0.0288(12) -0.0079(10) -0.0010(10) 0.0027(10) C1 0.0276(17) 0.0256(16) 0.0221(15) -0.0013(13) 0.0018(13) -0.0018(13) C2 0.0250(16) 0.0220(15) 0.0195(14) 0.0002(11) 0.0014(12) -0.0003(12) N1 0.0228(13) 0.0241(13) 0.0201(12) -0.0011(10) -0.0008(10) -0.0011(11) N2 0.0230(13) 0.0226(13) 0.0232(13) 0.0012(10) -0.0027(10) 0.0015(10) N3 0.0248(14) 0.0238(14) 0.0240(13) -0.0011(11) -0.0022(11) 0.0036(11) N4 0.0274(14) 0.0236(14) 0.0240(13) -0.0019(11) -0.0001(11) -0.0002(11) N11 0.0236(14) 0.0236(13) 0.0210(12) -0.0026(10) -0.0006(11) -0.0003(10) N12 0.0253(15) 0.0284(15) 0.0275(14) 0.0021(11) -0.0030(12) 0.0016(11) C11 0.0259(16) 0.0214(15) 0.0238(15) -0.0032(12) 0.0013(12) -0.0030(12) C12 0.0241(16) 0.0245(15) 0.0252(15) 0.0027(12) 0.0007(13) 0.0002(13) C13 0.0236(16) 0.0248(16) 0.0203(14) -0.0006(12) -0.0015(12) 0.0024(12) C14 0.0251(16) 0.0254(16) 0.0215(15) 0.0010(12) 0.0000(12) -0.0038(12) C15 0.0263(16) 0.0221(15) 0.0232(15) 0.0026(12) 0.0015(13) 0.0015(13) O1W 0.0262(12) 0.0476(15) 0.0248(12) 0.0121(11) 0.0010(9) -0.0005(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.985(2) . ? Cu1 N2 1.992(3) 3_566 ? Cu1 N11 1.996(3) . ? Cu1 N1 2.003(3) . ? Cu1 O1W 2.202(3) . ? O1 C1 1.285(4) . ? O2 C1 1.234(4) . ? C1 C2 1.503(4) . ? C2 N1 1.331(4) . ? C2 N4 1.334(4) . ? N1 N2 1.343(4) . ? N2 N3 1.321(4) . ? N2 Cu1 1.992(3) 3_566 ? N3 N4 1.354(4) . ? N11 C11 1.344(4) . ? N11 C15 1.349(4) . ? N12 N12 1.250(6) 3_767 ? N12 C13 1.438(4) . ? C11 C12 1.402(4) . ? C12 C13 1.392(5) . ? C13 C14 1.396(4) . ? C14 C15 1.374(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 O1 Cu1 N2 172.81(11) . 3_566 ? O1 Cu1 N11 87.87(10) . . ? N2 Cu1 N11 95.89(11) 3_566 . ? O1 Cu1 N1 81.54(10) . . ? N2 Cu1 N1 93.68(11) 3_566 . ? N11 Cu1 N1 165.70(11) . . ? O1 Cu1 O1W 93.73(11) . . ? N2 Cu1 O1W 91.75(12) 3_566 . ? N11 Cu1 O1W 98.72(11) . . ? N1 Cu1 O1W 91.58(11) . . ? C1 O1 Cu1 116.8(2) . . ? O2 C1 O1 126.4(3) . . ? O2 C1 C2 120.9(3) . . ? O1 C1 C2 112.7(3) . . ? N1 C2 N4 112.3(3) . . ? N1 C2 C1 117.1(3) . . ? N4 C2 C1 130.6(3) . . ? C2 N1 N2 104.7(3) . . ? C2 N1 Cu1 111.8(2) . . ? N2 N1 Cu1 143.4(2) . . ? N3 N2 N1 109.5(2) . . ? N3 N2 Cu1 127.6(2) . 3_566 ? N1 N2 Cu1 122.8(2) . 3_566 ? N2 N3 N4 109.2(2) . . ? C2 N4 N3 104.3(3) . . ? C11 N11 C15 118.8(3) . . ? C11 N11 Cu1 125.8(2) . . ? C15 N11 Cu1 115.4(2) . . ? N12 N12 C13 113.5(3) 3_767 . ? N11 C11 C12 122.3(3) . . ? C13 C12 C11 118.0(3) . . ? C12 C13 C14 119.4(3) . . ? C12 C13 N12 117.1(3) . . ? C14 C13 N12 123.5(3) . . ? C15 C14 C13 118.8(3) . . ? N11 C15 C14 122.6(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.643 _refine_diff_density_min -0.661 _refine_diff_density_rms 0.099