# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10.25 H12 Cu N O5' _chemical_formula_weight 292.75 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 Tetragonal _symmetry_space_group_name_H-M P42/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 14.4216(4) _cell_length_b 14.4216(4) _cell_length_c 14.7640(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3070.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 1.430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.712 _exptl_absorpt_correction_T_max 0.748 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16701 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3033 _reflns_number_gt 1941 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1151P)^2^+1.0910P] 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 3033 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1910 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.83433(3) 0.28652(3) 1.00156(3) 0.0384(2) Uani 1 1 d . . . O1 O 1.18568(17) 0.34184(18) 0.86926(19) 0.0526(7) Uani 1 1 d . . . O2 O 0.7846(2) 0.3678(2) 1.09503(19) 0.0566(7) Uani 1 1 d . . . O3 O 0.7812(2) 0.3670(2) 0.90710(19) 0.0567(7) Uani 1 1 d . . . O4 O 0.8573(2) 0.1915(2) 1.09542(19) 0.0574(8) Uani 1 1 d . . . O5 O 0.8605(2) 0.1937(2) 0.90721(19) 0.0576(8) Uani 1 1 d . . . N1 N 0.9741(2) 0.3433(2) 1.00497(17) 0.0430(8) Uani 1 1 d . . . C1 C 1.0016(3) 0.4012(3) 1.0703(3) 0.0488(9) Uani 1 1 d . . . H1A H 0.9601 0.4157 1.1165 0.059 Uiso 1 1 calc R . . C2 C 1.0893(3) 0.4406(3) 1.0721(3) 0.0552(11) Uani 1 1 d . . . H2A H 1.1066 0.4802 1.1189 0.066 Uiso 1 1 calc R . . C3 C 1.1498(3) 0.4201(3) 1.0038(3) 0.0525(11) Uani 1 1 d . . . H3A H 1.2087 0.4463 1.0030 0.063 Uiso 1 1 calc R . . C4 C 1.1229(2) 0.3603(3) 0.9361(2) 0.0416(8) Uani 1 1 d . . . C5 C 1.0339(2) 0.3223(3) 0.9388(2) 0.0428(9) Uani 1 1 d . . . H5A H 1.0158 0.2814 0.8934 0.051 Uiso 1 1 calc R . . C6 C 1.1648(2) 0.2680(2) 0.8090(2) 0.0409(8) Uani 1 1 d . . . H6A H 1.1123 0.2844 0.7712 0.049 Uiso 1 1 calc R . . H6B H 1.1491 0.2126 0.8429 0.049 Uiso 1 1 calc R . . C7 C 1.2500 0.2500 0.7500 0.0407(16) Uani 1 4 d S . . C10 C 0.8006(3) 0.1387(3) 0.8789(3) 0.0467(9) Uani 1 1 d . . . C11 C 0.8288(4) 0.0739(4) 0.8032(3) 0.0747(14) Uani 1 1 d . . . H11A H 0.7772 0.0351 0.7872 0.112 Uiso 1 1 calc R . . H11B H 0.8796 0.0359 0.8229 0.112 Uiso 1 1 calc R . . H11C H 0.8474 0.1096 0.7514 0.112 Uiso 1 1 calc R . . C12 C 0.7029(3) 0.3628(3) 1.1238(3) 0.0464(9) Uani 1 1 d . . . C13 C 0.6759(4) 0.4282(4) 1.1987(3) 0.0748(14) Uani 1 1 d . . . H13A H 0.6122 0.4179 1.2148 0.112 Uiso 1 1 calc R . . H13B H 0.6836 0.4910 1.1786 0.112 Uiso 1 1 calc R . . H13C H 0.7146 0.4173 1.2505 0.112 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 0.0380(3) 0.0426(3) 0.0346(3) -0.00099(18) 0.00135(18) -0.01013(18) O1 0.0425(14) 0.0576(17) 0.0576(17) -0.0173(13) 0.0126(13) -0.0166(12) O2 0.0586(18) 0.0581(17) 0.0530(17) -0.0168(14) 0.0056(14) -0.0118(14) O3 0.0628(19) 0.0556(17) 0.0516(16) 0.0142(13) -0.0074(14) -0.0178(14) O4 0.0539(17) 0.0646(18) 0.0536(17) 0.0160(14) -0.0087(14) -0.0044(14) O5 0.0539(16) 0.0651(18) 0.0537(17) -0.0168(14) 0.0094(14) -0.0094(14) N1 0.0387(17) 0.0495(19) 0.0408(18) 0.0002(14) 0.0010(13) -0.0074(14) C1 0.051(2) 0.055(2) 0.040(2) -0.0072(18) 0.0066(18) -0.0099(19) C2 0.058(2) 0.062(3) 0.046(2) -0.013(2) 0.001(2) -0.016(2) C3 0.042(2) 0.056(3) 0.060(3) -0.010(2) 0.0028(18) -0.0184(19) C4 0.0374(19) 0.048(2) 0.0390(19) -0.0018(17) 0.0008(16) -0.0045(16) C5 0.0404(19) 0.048(2) 0.0402(19) -0.0047(17) 0.0043(17) -0.0094(16) C6 0.0344(19) 0.046(2) 0.0428(19) -0.0063(17) 0.0015(16) -0.0054(15) C7 0.039(2) 0.039(2) 0.043(4) 0.000 0.000 0.000 C10 0.061(3) 0.043(2) 0.036(2) -0.0009(17) 0.0050(19) -0.0028(19) C11 0.099(4) 0.071(3) 0.055(3) -0.024(2) 0.012(3) -0.001(3) C12 0.057(3) 0.044(2) 0.038(2) -0.0038(18) 0.0033(18) 0.0001(19) C13 0.097(4) 0.068(3) 0.060(3) -0.024(3) 0.012(3) 0.004(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 O2 1.948(3) . ? Cu1 O5 1.968(3) . ? Cu1 O3 1.970(3) . ? Cu1 O4 1.977(3) . ? Cu1 N1 2.177(3) . ? Cu1 Cu1 2.6506(9) 2_655 ? O1 C4 1.366(4) . ? O1 C6 1.421(4) . ? O2 C12 1.255(5) . ? O3 C10 1.252(5) 2_655 ? O4 C12 1.242(5) 2_655 ? O5 C10 1.245(5) . ? N1 C1 1.336(4) . ? N1 C5 1.338(4) . ? C1 C2 1.387(5) . ? C2 C3 1.367(6) . ? C3 C4 1.375(5) . ? C4 C5 1.395(5) . ? C6 C7 1.527(3) . ? C7 C6 1.527(3) 8_747 ? C7 C6 1.528(3) 2_755 ? C7 C6 1.528(3) 7_677 ? C10 O3 1.252(5) 2_655 ? C10 C11 1.513(6) . ? C12 O4 1.242(5) 2_655 ? C12 C13 1.504(6) . ? 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 O5 168.92(13) . . ? O2 Cu1 O3 90.22(15) . . ? O5 Cu1 O3 88.51(14) . . ? O2 Cu1 O4 88.99(14) . . ? O5 Cu1 O4 89.57(15) . . ? O3 Cu1 O4 165.92(13) . . ? O2 Cu1 N1 95.63(12) . . ? O5 Cu1 N1 95.45(12) . . ? O3 Cu1 N1 98.93(12) . . ? O4 Cu1 N1 95.13(12) . . ? O2 Cu1 Cu1 84.35(9) . 2_655 ? O5 Cu1 Cu1 84.57(9) . 2_655 ? O3 Cu1 Cu1 82.93(9) . 2_655 ? O4 Cu1 Cu1 83.01(9) . 2_655 ? N1 Cu1 Cu1 178.14(8) . 2_655 ? C4 O1 C6 117.3(3) . . ? C12 O2 Cu1 123.4(3) . . ? C10 O3 Cu1 124.2(3) 2_655 . ? C12 O4 Cu1 123.8(3) 2_655 . ? C10 O5 Cu1 122.5(3) . . ? C1 N1 C5 118.5(3) . . ? C1 N1 Cu1 121.8(2) . . ? C5 N1 Cu1 119.7(2) . . ? N1 C1 C2 122.7(4) . . ? C3 C2 C1 118.7(4) . . ? C2 C3 C4 119.4(4) . . ? O1 C4 C3 117.4(3) . . ? O1 C4 C5 123.6(3) . . ? C3 C4 C5 119.0(3) . . ? N1 C5 C4 121.6(3) . . ? O1 C6 C7 108.3(2) . . ? C6 C7 C6 108.95(13) 8_747 . ? C6 C7 C6 108.95(13) 8_747 2_755 ? C6 C7 C6 110.5(3) . 2_755 ? C6 C7 C6 110.5(3) 8_747 7_677 ? C6 C7 C6 108.94(13) . 7_677 ? C6 C7 C6 108.94(13) 2_755 7_677 ? O5 C10 O3 125.7(4) . 2_655 ? O5 C10 C11 117.0(4) . . ? O3 C10 C11 117.3(4) 2_655 . ? O4 C12 O2 125.3(4) 2_655 . ? O4 C12 C13 117.5(4) 2_655 . ? O2 C12 C13 117.1(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.495 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.123 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.023 -0.017 -0.035 929 126 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 950216' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H48 Cu2 N4 O14' _chemical_formula_weight 1092.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 11.5577(9) _cell_length_b 15.1458(12) _cell_length_c 15.1471(12) _cell_angle_alpha 85.080(2) _cell_angle_beta 86.468(2) _cell_angle_gamma 74.596(2) _cell_volume 2544.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.796 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14174 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.1255 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 26.03 _reflns_number_total 9893 _reflns_number_gt 5487 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0803P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9893 _refine_ls_number_parameters 658 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1252 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1737 _refine_ls_wR_factor_gt 0.1527 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 0.32104(6) 1.09343(4) 0.54482(4) 0.03272(19) Uani 1 1 d . . . Cu2 Cu -0.09460(5) 0.48603(5) 0.87926(4) 0.03213(19) Uani 1 1 d . . . N1 N 0.0767(3) 0.4270(3) 0.8387(3) 0.0280(10) Uani 1 1 d . . . N2 N 0.7321(4) 0.5415(3) 0.9140(3) 0.0342(11) Uani 1 1 d . . . N3 N 0.2409(4) 0.9971(3) 0.5184(3) 0.0297(10) Uani 1 1 d . . . N4 N 0.5805(4) 0.8201(3) 0.4314(3) 0.0319(10) Uani 1 1 d . . . O1 O 0.3232(3) 0.4978(2) 0.7178(2) 0.0337(9) Uani 1 1 d . . . O1W O 0.8548(4) 0.2771(3) 0.6761(3) 0.0580(12) Uani 1 1 d . . . O2 O 0.4444(3) 0.6233(3) 0.8087(2) 0.0373(9) Uani 1 1 d . . . O2W O 0.7370(6) 0.2982(4) 0.8494(4) 0.117(2) Uani 1 1 d . . . O3 O 0.2354(3) 0.7626(2) 0.5957(2) 0.0356(9) Uani 1 1 d . . . O4 O 0.5174(3) 0.6139(2) 0.5324(2) 0.0334(9) Uani 1 1 d . . . O5 O -0.1093(3) 0.5673(2) 0.7684(2) 0.0307(8) Uani 1 1 d . . . O6 O -0.1473(3) 0.4449(3) 0.7187(2) 0.0419(10) Uani 1 1 d . . . O7 O -0.1016(3) 0.3845(3) 0.9669(3) 0.0493(11) Uani 1 1 d . . . O8 O 0.0355(4) 0.4026(3) 1.0530(3) 0.0505(11) Uani 1 1 d . . . O9 O 0.0837(3) 1.1471(3) 0.6458(2) 0.0420(10) Uani 1 1 d . . . O10 O 0.2774(3) 1.0826(2) 0.6701(2) 0.0341(9) Uani 1 1 d . . . O11 O 0.3180(3) 1.1366(3) 0.4198(2) 0.0393(9) Uani 1 1 d . . . O12 O 0.5024(4) 1.0446(3) 0.4043(3) 0.0485(11) Uani 1 1 d . . . C1 C 0.3762(4) 0.6322(4) 0.6614(3) 0.0284(12) Uani 1 1 d . . . C2 C 0.2740(4) 0.5946(3) 0.7046(3) 0.0278(12) Uani 1 1 d . . . H2A H 0.2470 0.6211 0.7607 0.033 Uiso 1 1 calc R . . H2B H 0.2065 0.6086 0.6661 0.033 Uiso 1 1 calc R . . C3 C 0.4842(4) 0.6031(4) 0.7193(3) 0.0313(12) Uani 1 1 d . . . H3A H 0.5212 0.5379 0.7167 0.038 Uiso 1 1 calc R . . H3B H 0.5432 0.6361 0.6986 0.038 Uiso 1 1 calc R . . C4 C 0.3350(4) 0.7369(3) 0.6525(3) 0.0297(12) Uani 1 1 d . . . H4A H 0.3111 0.7605 0.7103 0.036 Uiso 1 1 calc R . . H4B H 0.3998 0.7619 0.6273 0.036 Uiso 1 1 calc R . . C5 C 0.4103(4) 0.5919(4) 0.5721(3) 0.0315(12) Uani 1 1 d . . . H5A H 0.4239 0.5258 0.5797 0.038 Uiso 1 1 calc R . . H5B H 0.3444 0.6159 0.5326 0.038 Uiso 1 1 calc R . . C6 C 0.2563(4) 0.4466(3) 0.7636(3) 0.0262(12) Uani 1 1 d . . . C7 C 0.3093(5) 0.3538(4) 0.7764(4) 0.0370(14) Uani 1 1 d . . . H7A H 0.3875 0.3290 0.7553 0.044 Uiso 1 1 calc R . . C8 C 0.2452(5) 0.2993(4) 0.8206(4) 0.0499(17) Uani 1 1 d . . . H8A H 0.2795 0.2365 0.8304 0.060 Uiso 1 1 calc R . . C9 C 0.1285(5) 0.3377(4) 0.8508(4) 0.0425(15) Uani 1 1 d . . . H9A H 0.0851 0.2997 0.8805 0.051 Uiso 1 1 calc R . . C10 C 0.1395(4) 0.4807(3) 0.7952(3) 0.0273(12) Uani 1 1 d . . . H10A H 0.1034 0.5432 0.7859 0.033 Uiso 1 1 calc R . . C11 C 0.5296(4) 0.6003(4) 0.8712(3) 0.0347(13) Uani 1 1 d . . . C12 C 0.4921(5) 0.6203(4) 0.9570(4) 0.0428(15) Uani 1 1 d . . . H12A H 0.4116 0.6459 0.9718 0.051 Uiso 1 1 calc R . . C13 C 0.5770(5) 0.6012(5) 1.0195(4) 0.0517(17) Uani 1 1 d . . . H13A H 0.5548 0.6149 1.0778 0.062 Uiso 1 1 calc R . . C14 C 0.6960(5) 0.5617(4) 0.9965(4) 0.0432(15) Uani 1 1 d . . . H14A H 0.7525 0.5489 1.0401 0.052 Uiso 1 1 calc R . . C15 C 0.6496(4) 0.5595(4) 0.8524(3) 0.0330(13) Uani 1 1 d . . . H15A H 0.6736 0.5440 0.7948 0.040 Uiso 1 1 calc R . . C16 C 0.2114(4) 0.8476(4) 0.5505(3) 0.0309(12) Uani 1 1 d . . . C17 C 0.1350(5) 0.8617(4) 0.4804(4) 0.0382(14) Uani 1 1 d . . . H17A H 0.0995 0.8162 0.4675 0.046 Uiso 1 1 calc R . . C18 C 0.1132(5) 0.9432(4) 0.4311(4) 0.0423(15) Uani 1 1 d . . . H18A H 0.0620 0.9542 0.3841 0.051 Uiso 1 1 calc R . . C19 C 0.1675(5) 1.0096(4) 0.4512(4) 0.0368(13) Uani 1 1 d . . . H19A H 0.1523 1.0650 0.4167 0.044 Uiso 1 1 calc R . . C20 C 0.2616(4) 0.9177(4) 0.5672(3) 0.0302(12) Uani 1 1 d . . . H20A H 0.3120 0.9088 0.6146 0.036 Uiso 1 1 calc R . . C21 C 0.5042(4) 0.6903(4) 0.4751(3) 0.0304(12) Uani 1 1 d . . . C22 C 0.4219(5) 0.7144(4) 0.4093(3) 0.0375(14) Uani 1 1 d . . . H22A H 0.3688 0.6793 0.4017 0.045 Uiso 1 1 calc R . . C23 C 0.4212(5) 0.7931(4) 0.3546(4) 0.0413(15) Uani 1 1 d . . . H23A H 0.3665 0.8117 0.3098 0.050 Uiso 1 1 calc R . . C24 C 0.5007(5) 0.8429(4) 0.3666(4) 0.0389(14) Uani 1 1 d . . . H24A H 0.4998 0.8947 0.3287 0.047 Uiso 1 1 calc R . . C25 C 0.5822(4) 0.7449(4) 0.4835(3) 0.0309(12) Uani 1 1 d . . . H25A H 0.6380 0.7279 0.5277 0.037 Uiso 1 1 calc R . . C26 C -0.1278(4) 0.5670(4) 0.6132(3) 0.0320(13) Uani 1 1 d . . . C27 C -0.0922(4) 0.6466(4) 0.5948(4) 0.0349(13) Uani 1 1 d . . . H27A H -0.0697 0.6750 0.6405 0.042 Uiso 1 1 calc R . . C28 C -0.0899(5) 0.6849(4) 0.5081(4) 0.0412(14) Uani 1 1 d . . . H28A H -0.0652 0.7385 0.4961 0.049 Uiso 1 1 calc R . . C29 C -0.1238(5) 0.6441(4) 0.4403(4) 0.0444(15) Uani 1 1 d . . . H29A H -0.1223 0.6701 0.3825 0.053 Uiso 1 1 calc R . . C30 C -0.1600(5) 0.5648(4) 0.4576(4) 0.0466(16) Uani 1 1 d . . . H30A H -0.1827 0.5370 0.4115 0.056 Uiso 1 1 calc R . . C31 C -0.1627(5) 0.5266(4) 0.5428(4) 0.0377(14) Uani 1 1 d . . . H31A H -0.1881 0.4732 0.5542 0.045 Uiso 1 1 calc R . . C32 C -0.0656(5) 0.2864(4) 1.0966(3) 0.0346(13) Uani 1 1 d . . . C33 C -0.1469(5) 0.2392(4) 1.0792(4) 0.0475(16) Uani 1 1 d . . . H33A H -0.1927 0.2563 1.0291 0.057 Uiso 1 1 calc R . . C34 C -0.1607(6) 0.1651(4) 1.1371(4) 0.0519(17) Uani 1 1 d . . . H34A H -0.2153 0.1328 1.1250 0.062 Uiso 1 1 calc R . . C35 C -0.0954(6) 0.1402(4) 1.2106(4) 0.0505(17) Uani 1 1 d . . . H35A H -0.1039 0.0903 1.2481 0.061 Uiso 1 1 calc R . . C36 C -0.0179(6) 0.1882(4) 1.2292(4) 0.0503(17) Uani 1 1 d . . . H36A H 0.0252 0.1722 1.2806 0.060 Uiso 1 1 calc R . . C37 C -0.0021(5) 0.2611(4) 1.1722(4) 0.0426(15) Uani 1 1 d . . . H37A H 0.0522 0.2932 1.1854 0.051 Uiso 1 1 calc R . . C38 C -0.0429(5) 0.3655(4) 1.0342(4) 0.0432(15) Uani 1 1 d . . . C39 C -0.1278(4) 0.5226(4) 0.7050(4) 0.0324(13) Uani 1 1 d . . . C40 C 0.1420(5) 1.0995(4) 0.7946(4) 0.0342(13) Uani 1 1 d . . . C41 C 0.0252(5) 1.1121(4) 0.8279(4) 0.0454(15) Uani 1 1 d . . . H41A H -0.0377 1.1257 0.7893 0.054 Uiso 1 1 calc R . . C42 C 0.0017(6) 1.1044(4) 0.9185(4) 0.0519(17) Uani 1 1 d . . . H42A H -0.0769 1.1115 0.9405 0.062 Uiso 1 1 calc R . . C43 C 0.0934(6) 1.0866(4) 0.9761(4) 0.0521(17) Uani 1 1 d . . . H43A H 0.0769 1.0832 1.0370 0.062 Uiso 1 1 calc R . . C44 C 0.2085(6) 1.0738(4) 0.9439(4) 0.0501(16) Uani 1 1 d . . . H44A H 0.2708 1.0616 0.9829 0.060 Uiso 1 1 calc R . . C45 C 0.2339(5) 1.0789(4) 0.8527(4) 0.0382(14) Uani 1 1 d . . . H45A H 0.3131 1.0684 0.8311 0.046 Uiso 1 1 calc R . . C46 C 0.1671(5) 1.1109(3) 0.6963(4) 0.0322(13) Uani 1 1 d . . . C47 C 0.4137(5) 1.1336(4) 0.2769(4) 0.0354(13) Uani 1 1 d . . . C48 C 0.5137(5) 1.0955(4) 0.2231(4) 0.0400(14) Uani 1 1 d . . . H48A H 0.5801 1.0535 0.2474 0.048 Uiso 1 1 calc R . . C49 C 0.5129(6) 1.1212(4) 0.1328(4) 0.0472(16) Uani 1 1 d . . . H49A H 0.5797 1.0962 0.0967 0.057 Uiso 1 1 calc R . . C50 C 0.4152(6) 1.1826(4) 0.0959(4) 0.0452(15) Uani 1 1 d . . . H50A H 0.4155 1.1985 0.0352 0.054 Uiso 1 1 calc R . . C51 C 0.3173(6) 1.2203(4) 0.1490(4) 0.0528(17) Uani 1 1 d . . . H51A H 0.2513 1.2625 0.1244 0.063 Uiso 1 1 calc R . . C52 C 0.3163(5) 1.1958(4) 0.2395(4) 0.0445(15) Uani 1 1 d . . . H52A H 0.2495 1.2216 0.2751 0.053 Uiso 1 1 calc R . . C53 C 0.4139(5) 1.1008(4) 0.3747(4) 0.0348(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 0.0366(4) 0.0350(4) 0.0285(4) -0.0026(3) 0.0049(3) -0.0140(3) Cu2 0.0268(3) 0.0394(4) 0.0289(4) 0.0074(3) -0.0024(3) -0.0092(3) N1 0.029(2) 0.027(3) 0.029(2) 0.0067(19) 0.0002(18) -0.011(2) N2 0.027(2) 0.045(3) 0.030(3) 0.007(2) -0.0060(19) -0.011(2) N3 0.029(2) 0.034(3) 0.024(2) 0.005(2) -0.0006(18) -0.008(2) N4 0.033(2) 0.034(3) 0.029(2) -0.002(2) 0.007(2) -0.011(2) O1 0.0299(19) 0.029(2) 0.041(2) 0.0032(17) 0.0054(16) -0.0093(17) O1W 0.053(3) 0.054(3) 0.070(3) -0.015(2) -0.002(2) -0.018(2) O2 0.0273(19) 0.056(3) 0.025(2) -0.0053(18) -0.0021(15) -0.0040(18) O2W 0.137(6) 0.090(4) 0.114(5) 0.007(4) 0.062(4) -0.033(4) O3 0.037(2) 0.031(2) 0.041(2) 0.0013(18) -0.0074(17) -0.0133(17) O4 0.030(2) 0.035(2) 0.034(2) 0.0010(17) 0.0076(16) -0.0110(17) O5 0.0315(19) 0.037(2) 0.0247(19) 0.0005(17) -0.0040(15) -0.0100(16) O6 0.058(3) 0.032(2) 0.039(2) -0.0028(18) 0.0026(19) -0.019(2) O7 0.037(2) 0.057(3) 0.042(3) 0.020(2) -0.0053(19) 0.001(2) O8 0.065(3) 0.044(3) 0.046(3) 0.005(2) -0.004(2) -0.022(2) O9 0.042(2) 0.043(3) 0.037(2) -0.0030(19) -0.0007(18) -0.0044(19) O10 0.032(2) 0.041(2) 0.029(2) -0.0007(17) 0.0049(16) -0.0111(17) O11 0.042(2) 0.045(3) 0.032(2) -0.0008(18) 0.0042(17) -0.0157(19) O12 0.046(2) 0.057(3) 0.037(2) 0.003(2) -0.0069(19) -0.005(2) C1 0.031(3) 0.031(3) 0.026(3) -0.004(2) -0.006(2) -0.010(2) C2 0.030(3) 0.026(3) 0.027(3) 0.001(2) -0.001(2) -0.008(2) C3 0.039(3) 0.033(3) 0.025(3) -0.005(2) 0.003(2) -0.016(3) C4 0.030(3) 0.037(3) 0.024(3) -0.004(2) -0.002(2) -0.010(2) C5 0.033(3) 0.034(3) 0.032(3) -0.005(2) 0.005(2) -0.016(2) C6 0.032(3) 0.031(3) 0.017(2) -0.006(2) 0.002(2) -0.010(2) C7 0.033(3) 0.030(3) 0.046(4) -0.004(3) 0.012(3) -0.007(3) C8 0.049(4) 0.024(3) 0.073(5) -0.002(3) 0.013(3) -0.006(3) C9 0.043(3) 0.035(4) 0.050(4) 0.007(3) 0.004(3) -0.014(3) C10 0.034(3) 0.020(3) 0.026(3) -0.002(2) -0.005(2) -0.003(2) C11 0.029(3) 0.048(4) 0.025(3) 0.001(3) -0.002(2) -0.007(3) C12 0.032(3) 0.066(4) 0.031(3) -0.006(3) -0.003(2) -0.012(3) C13 0.040(3) 0.084(5) 0.029(3) -0.008(3) -0.004(3) -0.010(3) C14 0.040(3) 0.060(4) 0.029(3) 0.001(3) -0.009(3) -0.011(3) C15 0.025(3) 0.045(4) 0.028(3) -0.004(3) 0.000(2) -0.007(2) C16 0.030(3) 0.034(3) 0.026(3) -0.004(2) 0.007(2) -0.005(2) C17 0.034(3) 0.042(4) 0.042(3) -0.001(3) -0.007(3) -0.016(3) C18 0.036(3) 0.051(4) 0.041(4) 0.003(3) -0.009(3) -0.013(3) C19 0.037(3) 0.034(3) 0.038(3) 0.009(3) -0.008(3) -0.010(3) C20 0.036(3) 0.033(3) 0.023(3) -0.003(2) -0.002(2) -0.010(3) C21 0.028(3) 0.029(3) 0.033(3) -0.003(2) 0.005(2) -0.006(2) C22 0.043(3) 0.049(4) 0.027(3) -0.005(3) 0.005(2) -0.023(3) C23 0.037(3) 0.052(4) 0.035(3) 0.002(3) -0.005(3) -0.012(3) C24 0.043(3) 0.042(4) 0.029(3) 0.009(3) 0.003(3) -0.013(3) C25 0.029(3) 0.036(3) 0.029(3) -0.004(3) 0.000(2) -0.011(2) C26 0.032(3) 0.038(4) 0.024(3) -0.003(2) 0.002(2) -0.005(3) C27 0.033(3) 0.037(4) 0.033(3) -0.004(3) 0.005(2) -0.008(3) C28 0.043(3) 0.037(4) 0.043(4) 0.013(3) -0.005(3) -0.013(3) C29 0.044(3) 0.052(4) 0.031(3) 0.003(3) 0.005(3) -0.006(3) C30 0.047(4) 0.061(5) 0.030(3) -0.008(3) 0.000(3) -0.010(3) C31 0.037(3) 0.035(4) 0.041(3) -0.004(3) -0.003(3) -0.008(3) C32 0.039(3) 0.030(3) 0.029(3) -0.005(2) 0.013(2) -0.001(3) C33 0.045(4) 0.054(4) 0.034(3) -0.007(3) -0.005(3) 0.006(3) C34 0.054(4) 0.059(5) 0.054(4) -0.025(4) 0.017(3) -0.032(3) C35 0.081(5) 0.028(4) 0.042(4) -0.003(3) 0.019(3) -0.019(3) C36 0.057(4) 0.047(4) 0.039(4) 0.004(3) -0.005(3) -0.001(3) C37 0.046(3) 0.035(4) 0.048(4) -0.007(3) 0.003(3) -0.012(3) C38 0.032(3) 0.049(4) 0.045(4) -0.009(3) 0.011(3) -0.005(3) C39 0.033(3) 0.030(3) 0.033(3) -0.001(3) 0.000(2) -0.007(3) C40 0.047(3) 0.025(3) 0.034(3) -0.004(2) 0.003(3) -0.016(3) C41 0.052(4) 0.049(4) 0.038(3) -0.009(3) 0.013(3) -0.020(3) C42 0.054(4) 0.054(4) 0.048(4) -0.008(3) 0.019(3) -0.018(3) C43 0.066(4) 0.054(4) 0.031(3) -0.001(3) 0.003(3) -0.008(3) C44 0.059(4) 0.046(4) 0.038(4) 0.003(3) -0.005(3) -0.003(3) C45 0.041(3) 0.027(3) 0.046(4) -0.001(3) 0.003(3) -0.009(3) C46 0.038(3) 0.020(3) 0.041(3) -0.002(2) -0.001(3) -0.012(2) C47 0.035(3) 0.036(3) 0.037(3) -0.004(3) 0.000(2) -0.012(3) C48 0.035(3) 0.045(4) 0.039(3) -0.010(3) 0.001(3) -0.005(3) C49 0.052(4) 0.057(4) 0.031(3) -0.005(3) 0.007(3) -0.014(3) C50 0.062(4) 0.049(4) 0.026(3) 0.007(3) -0.006(3) -0.018(3) C51 0.048(4) 0.056(4) 0.044(4) 0.014(3) -0.003(3) 0.001(3) C52 0.034(3) 0.048(4) 0.046(4) 0.001(3) 0.007(3) -0.005(3) C53 0.029(3) 0.038(4) 0.042(3) -0.006(3) 0.000(3) -0.017(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 O10 1.938(3) . ? Cu1 O11 1.949(4) . ? Cu1 N3 2.004(4) . ? Cu1 N4 2.017(4) 2_676 ? Cu2 O7 1.959(4) . ? Cu2 O5 1.983(3) . ? Cu2 N2 2.012(4) 1_455 ? Cu2 N1 2.025(4) . ? Cu2 O8 2.315(4) 2_567 ? N1 C9 1.327(6) . ? N1 C10 1.338(6) . ? N2 C14 1.327(7) . ? N2 C15 1.335(6) . ? N2 Cu2 2.012(4) 1_655 ? N3 C20 1.329(6) . ? N3 C19 1.334(6) . ? N4 C25 1.325(6) . ? N4 C24 1.347(7) . ? N4 Cu1 2.017(4) 2_676 ? O1 C6 1.357(6) . ? O1 C2 1.426(5) . ? O2 C11 1.365(6) . ? O2 C3 1.434(5) . ? O3 C16 1.373(6) . ? O3 C4 1.430(6) . ? O4 C21 1.366(6) . ? O4 C5 1.448(5) . ? O5 C39 1.281(6) . ? O6 C39 1.254(6) . ? O7 C38 1.231(7) . ? O8 C38 1.244(7) . ? O8 Cu2 2.315(4) 2_567 ? O9 C46 1.246(6) . ? O10 C46 1.282(6) . ? O11 C53 1.280(6) . ? O12 C53 1.226(6) . ? C1 C3 1.516(7) . ? C1 C5 1.518(7) . ? C1 C4 1.526(7) . ? C1 C2 1.531(6) . ? C6 C7 1.379(7) . ? C6 C10 1.382(6) . ? C7 C8 1.359(7) . ? C8 C9 1.386(8) . ? C11 C12 1.377(7) . ? C11 C15 1.383(7) . ? C12 C13 1.363(7) . ? C13 C14 1.382(8) . ? C16 C20 1.386(7) . ? C16 C17 1.389(7) . ? C17 C18 1.358(7) . ? C18 C19 1.382(7) . ? C21 C22 1.379(7) . ? C21 C25 1.394(7) . ? C22 C23 1.390(7) . ? C23 C24 1.364(7) . ? C26 C27 1.376(7) . ? C26 C31 1.402(7) . ? C26 C39 1.492(7) . ? C27 C28 1.391(7) . ? C28 C29 1.370(8) . ? C29 C30 1.374(8) . ? C30 C31 1.371(7) . ? C32 C37 1.368(8) . ? C32 C33 1.373(8) . ? C32 C38 1.529(8) . ? C33 C34 1.401(8) . ? C34 C35 1.353(9) . ? C35 C36 1.350(8) . ? C36 C37 1.387(8) . ? C40 C45 1.376(7) . ? C40 C41 1.381(7) . ? C40 C46 1.503(7) . ? C41 C42 1.384(8) . ? C42 C43 1.371(9) . ? C43 C44 1.358(8) . ? C44 C45 1.395(7) . ? C47 C52 1.378(8) . ? C47 C48 1.393(7) . ? C47 C53 1.522(7) . ? C48 C49 1.390(7) . ? C49 C50 1.372(8) . ? C50 C51 1.370(8) . ? C51 C52 1.389(8) . ? 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 O10 Cu1 O11 161.49(15) . . ? O10 Cu1 N3 92.15(16) . . ? O11 Cu1 N3 89.80(16) . . ? O10 Cu1 N4 89.99(16) . 2_676 ? O11 Cu1 N4 90.11(16) . 2_676 ? N3 Cu1 N4 173.52(17) . 2_676 ? O7 Cu2 O5 162.73(17) . . ? O7 Cu2 N2 86.68(16) . 1_455 ? O5 Cu2 N2 90.94(15) . 1_455 ? O7 Cu2 N1 93.55(16) . . ? O5 Cu2 N1 87.90(15) . . ? N2 Cu2 N1 176.79(18) 1_455 . ? O7 Cu2 O8 109.24(17) . 2_567 ? O5 Cu2 O8 87.90(14) . 2_567 ? N2 Cu2 O8 91.34(17) 1_455 2_567 ? N1 Cu2 O8 91.61(16) . 2_567 ? C9 N1 C10 118.4(4) . . ? C9 N1 Cu2 123.6(3) . . ? C10 N1 Cu2 118.0(3) . . ? C14 N2 C15 118.2(5) . . ? C14 N2 Cu2 122.4(4) . 1_655 ? C15 N2 Cu2 119.4(4) . 1_655 ? C20 N3 C19 118.3(5) . . ? C20 N3 Cu1 120.2(3) . . ? C19 N3 Cu1 121.5(4) . . ? C25 N4 C24 117.9(5) . . ? C25 N4 Cu1 121.8(4) . 2_676 ? C24 N4 Cu1 119.9(4) . 2_676 ? C6 O1 C2 118.9(4) . . ? C11 O2 C3 116.8(4) . . ? C16 O3 C4 118.4(4) . . ? C21 O4 C5 118.4(4) . . ? C39 O5 Cu2 108.5(3) . . ? C38 O7 Cu2 124.2(4) . . ? C38 O8 Cu2 151.3(4) . 2_567 ? C46 O10 Cu1 119.6(3) . . ? C53 O11 Cu1 114.1(4) . . ? C3 C1 C5 109.1(4) . . ? C3 C1 C4 108.7(4) . . ? C5 C1 C4 112.1(4) . . ? C3 C1 C2 109.7(4) . . ? C5 C1 C2 108.2(4) . . ? C4 C1 C2 109.2(4) . . ? O1 C2 C1 105.5(4) . . ? O2 C3 C1 108.3(4) . . ? O3 C4 C1 107.6(4) . . ? O4 C5 C1 111.5(4) . . ? O1 C6 C7 116.5(4) . . ? O1 C6 C10 124.6(5) . . ? C7 C6 C10 118.9(5) . . ? C8 C7 C6 118.7(5) . . ? C7 C8 C9 119.6(5) . . ? N1 C9 C8 122.1(5) . . ? N1 C10 C6 122.3(5) . . ? O2 C11 C12 117.1(5) . . ? O2 C11 C15 123.5(5) . . ? C12 C11 C15 119.3(5) . . ? C13 C12 C11 117.8(5) . . ? C12 C13 C14 120.3(6) . . ? N2 C14 C13 122.0(5) . . ? N2 C15 C11 122.4(5) . . ? O3 C16 C20 124.9(5) . . ? O3 C16 C17 116.6(5) . . ? C20 C16 C17 118.4(5) . . ? C18 C17 C16 118.7(5) . . ? C17 C18 C19 119.7(5) . . ? N3 C19 C18 122.2(5) . . ? N3 C20 C16 122.7(5) . . ? O4 C21 C22 124.2(5) . . ? O4 C21 C25 116.7(5) . . ? C22 C21 C25 119.1(5) . . ? C21 C22 C23 117.6(5) . . ? C24 C23 C22 120.0(5) . . ? N4 C24 C23 122.6(5) . . ? N4 C25 C21 122.9(5) . . ? C27 C26 C31 118.4(5) . . ? C27 C26 C39 121.6(5) . . ? C31 C26 C39 120.0(5) . . ? C26 C27 C28 120.3(5) . . ? C29 C28 C27 120.3(5) . . ? C28 C29 C30 120.1(5) . . ? C31 C30 C29 120.0(6) . . ? C30 C31 C26 120.9(5) . . ? C37 C32 C33 118.7(5) . . ? C37 C32 C38 119.1(5) . . ? C33 C32 C38 122.3(5) . . ? C32 C33 C34 119.7(6) . . ? C35 C34 C33 120.6(6) . . ? C36 C35 C34 119.8(6) . . ? C35 C36 C37 120.5(6) . . ? C32 C37 C36 120.7(6) . . ? O7 C38 O8 125.3(6) . . ? O7 C38 C32 116.2(6) . . ? O8 C38 C32 118.4(6) . . ? O6 C39 O5 121.9(5) . . ? O6 C39 C26 120.4(5) . . ? O5 C39 C26 117.7(5) . . ? C45 C40 C41 119.1(5) . . ? C45 C40 C46 120.8(5) . . ? C41 C40 C46 120.1(5) . . ? C40 C41 C42 120.1(6) . . ? C43 C42 C41 120.5(6) . . ? C44 C43 C42 119.7(6) . . ? C43 C44 C45 120.5(6) . . ? C40 C45 C44 120.1(5) . . ? O9 C46 O10 123.9(5) . . ? O9 C46 C40 120.3(5) . . ? O10 C46 C40 115.7(5) . . ? C52 C47 C48 119.4(5) . . ? C52 C47 C53 122.3(5) . . ? C48 C47 C53 118.2(5) . . ? C49 C48 C47 119.2(5) . . ? C50 C49 C48 121.1(6) . . ? C51 C50 C49 119.6(6) . . ? C50 C51 C52 120.3(6) . . ? C47 C52 C51 120.5(5) . . ? O12 C53 O11 125.3(5) . . ? O12 C53 C47 119.6(5) . . ? O11 C53 C47 115.1(5) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.821 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.098 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.000 200 60 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 950217' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6.25 H6 Cu0.25 N O1.50' _chemical_formula_weight 135.01 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 Tetragonal _symmetry_space_group_name_H-M P-4n2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' 'y+1/2, x+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' _cell_length_a 9.5268(6) _cell_length_b 9.5268(6) _cell_length_c 23.401(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2123.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 0.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6575 _exptl_absorpt_correction_T_max 0.7543 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11115 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 26.06 _reflns_number_total 2122 _reflns_number_gt 1490 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0552P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 2122 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 1.0000 0.7500 0.0479(2) Uani 1 4 d S . . N1 N 0.6026(3) 0.8873(3) 0.81027(9) 0.0488(6) Uani 1 1 d . . . O1 O 0.8317(3) 0.9578(2) 0.92672(10) 0.0560(6) Uani 1 1 d . . . O1W O 0.3153(2) 0.8153(2) 0.7500 0.0761(10) Uani 1 2 d S . . C1 C 1.0000 1.0000 1.0000 0.0471(15) Uani 1 4 d S . . C2 C 0.9283(3) 0.8865(3) 0.96361(12) 0.0436(8) Uani 1 1 d . . . H2A H 0.9974 0.8356 0.9413 0.052 Uiso 1 1 calc R . . H2B H 0.8789 0.8204 0.9879 0.052 Uiso 1 1 calc R . . C3 C 0.7571(4) 0.8767(3) 0.88978(14) 0.0491(8) Uani 1 1 d . . . C4 C 0.7512(5) 0.7326(4) 0.89000(15) 0.0672(10) Uani 1 1 d . . . H4A H 0.7995 0.6801 0.9171 0.081 Uiso 1 1 calc R . . C5 C 0.6719(5) 0.6699(4) 0.84908(19) 0.0847(14) Uani 1 1 d . . . H5A H 0.6683 0.5724 0.8477 0.102 Uiso 1 1 calc R . . C6 C 0.5975(5) 0.7449(4) 0.81007(16) 0.0656(10) Uani 1 1 d . . . H6A H 0.5428 0.6985 0.7831 0.079 Uiso 1 1 calc R . . C7 C 0.6798(4) 0.9507(4) 0.84980(12) 0.0477(8) Uani 1 1 d . . . H7A H 0.6820 1.0482 0.8507 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0588(3) 0.0588(3) 0.0260(3) 0.000 0.000 0.0087(4) N1 0.064(2) 0.052(2) 0.0305(12) -0.0006(14) -0.0015(14) 0.0057(12) O1 0.0749(16) 0.0510(14) 0.0420(13) -0.0038(11) -0.0192(12) 0.0060(11) O1W 0.0770(14) 0.0770(14) 0.074(2) -0.0179(19) 0.0179(19) -0.0128(17) C1 0.059(2) 0.059(2) 0.023(3) 0.000 0.000 0.000 C2 0.0457(19) 0.050(2) 0.0348(17) 0.0040(14) -0.0107(15) -0.0008(15) C3 0.064(2) 0.0492(19) 0.0340(16) -0.0001(15) -0.0087(16) 0.0041(17) C4 0.096(3) 0.043(2) 0.063(2) 0.001(2) -0.028(2) 0.0087(19) C5 0.126(4) 0.045(2) 0.083(3) -0.003(2) -0.034(3) 0.003(2) C6 0.103(3) 0.042(2) 0.052(2) -0.0048(17) -0.020(2) 0.003(2) C7 0.072(2) 0.0389(18) 0.0318(17) -0.0035(14) -0.0046(17) 0.0041(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.024(2) . ? Cu1 N1 2.024(2) 8_666 ? Cu1 N1 2.024(2) 2_675 ? Cu1 N1 2.024(2) 7_456 ? Cu1 O1W 2.488(3) 2_675 ? Cu1 O1W 2.488(3) . ? N1 C7 1.327(4) . ? N1 C6 1.357(4) . ? O1 C3 1.360(4) . ? O1 C2 1.433(4) . ? C1 C2 1.536(3) 4_757 ? C1 C2 1.536(3) . ? C1 C2 1.536(3) 2_775 ? C1 C2 1.536(3) 3_577 ? C3 C4 1.374(5) . ? C3 C7 1.383(4) . ? C4 C5 1.358(6) . ? C5 C6 1.359(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 N1 Cu1 N1 88.48(13) . 8_666 ? N1 Cu1 N1 91.65(13) . 2_675 ? N1 Cu1 N1 176.2(2) 8_666 2_675 ? N1 Cu1 N1 176.2(2) . 7_456 ? N1 Cu1 N1 91.65(13) 8_666 7_456 ? N1 Cu1 N1 88.48(13) 2_675 7_456 ? N1 Cu1 O1W 91.92(10) . 2_675 ? N1 Cu1 O1W 88.08(10) 8_666 2_675 ? N1 Cu1 O1W 88.08(10) 2_675 2_675 ? N1 Cu1 O1W 91.92(10) 7_456 2_675 ? N1 Cu1 O1W 88.08(10) . . ? N1 Cu1 O1W 91.92(10) 8_666 . ? N1 Cu1 O1W 91.92(10) 2_675 . ? N1 Cu1 O1W 88.08(10) 7_456 . ? O1W Cu1 O1W 180.0 2_675 . ? C7 N1 C6 118.5(3) . . ? C7 N1 Cu1 120.8(2) . . ? C6 N1 Cu1 120.7(2) . . ? C3 O1 C2 116.7(2) . . ? C2 C1 C2 107.90(11) 4_757 . ? C2 C1 C2 107.90(11) 4_757 2_775 ? C2 C1 C2 112.7(2) . 2_775 ? C2 C1 C2 112.7(2) 4_757 3_577 ? C2 C1 C2 107.89(11) . 3_577 ? C2 C1 C2 107.89(11) 2_775 3_577 ? O1 C2 C1 106.6(2) . . ? O1 C3 C4 125.9(3) . . ? O1 C3 C7 114.8(3) . . ? C4 C3 C7 119.3(3) . . ? C5 C4 C3 117.4(3) . . ? C4 C5 C6 122.1(4) . . ? N1 C6 C5 120.3(3) . . ? N1 C7 C3 122.3(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.322 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.040 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.088 -0.080 0.182 1126 384 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 950218'