# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_jiao _database_code_depnum_ccdc_archive 'CCDC 817197' #TrackingRef 'complex1-Cu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 Cu2 N4 O10' _chemical_formula_weight 703.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.731(5) _cell_length_b 13.576(7) _cell_length_c 10.412(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.825(7) _cell_angle_gamma 90.00 _cell_volume 1370.7(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2220 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.633 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 6370 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2398 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.7247P] 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 2398 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.39471(4) 0.53157(3) 0.11863(3) 0.03027(14) Uani 1 1 d . . . C1 C 0.2944(4) 0.6726(2) -0.0893(3) 0.0414(8) Uani 1 1 d . . . H1A H 0.3839 0.6712 -0.1143 0.050 Uiso 1 1 calc R . . C2 C 0.1991(4) 0.7337(3) -0.1533(4) 0.0564(10) Uani 1 1 d . . . H2A H 0.2239 0.7735 -0.2202 0.068 Uiso 1 1 calc R . . C3 C 0.0673(4) 0.7350(3) -0.1169(4) 0.0560(10) Uani 1 1 d . . . H3A H 0.0017 0.7760 -0.1592 0.067 Uiso 1 1 calc R . . C4 C 0.0320(3) 0.6761(2) -0.0185(3) 0.0426(8) Uani 1 1 d . . . H4A H -0.0574 0.6765 0.0067 0.051 Uiso 1 1 calc R . . C5 C 0.1313(3) 0.6161(2) 0.0429(3) 0.0300(7) Uani 1 1 d . . . C6 C 0.1071(3) 0.5501(2) 0.1517(3) 0.0310(7) Uani 1 1 d . . . C7 C -0.0200(3) 0.5383(2) 0.2010(3) 0.0413(8) Uani 1 1 d . . . H7A H -0.0974 0.5711 0.1640 0.050 Uiso 1 1 calc R . . C8 C -0.0299(4) 0.4771(3) 0.3057(3) 0.0496(9) Uani 1 1 d . . . H8A H -0.1137 0.4688 0.3412 0.060 Uiso 1 1 calc R . . C9 C 0.0856(4) 0.4287(3) 0.3565(3) 0.0501(10) Uani 1 1 d . . . H9A H 0.0810 0.3870 0.4269 0.060 Uiso 1 1 calc R . . C10 C 0.2086(4) 0.4422(2) 0.3027(3) 0.0422(8) Uani 1 1 d . . . H10A H 0.2865 0.4092 0.3380 0.051 Uiso 1 1 calc R . . C11 C 0.6225(3) 0.6629(2) 0.0795(3) 0.0332(7) Uani 1 1 d . . . C12 C 0.5636(4) 0.7171(2) 0.1901(3) 0.0464(9) Uani 1 1 d . . . H12A H 0.6396 0.7432 0.2464 0.056 Uiso 1 1 calc R . . H12B H 0.5101 0.7727 0.1552 0.056 Uiso 1 1 calc R . . C13 C 0.5521(4) 0.6057(3) 0.3653(3) 0.0604(11) Uani 1 1 d . . . H13A H 0.5010 0.6097 0.4411 0.072 Uiso 1 1 calc R . . H13B H 0.6405 0.6375 0.3862 0.072 Uiso 1 1 calc R . . C14 C 0.5782(4) 0.4979(3) 0.3380(3) 0.0426(8) Uani 1 1 d . . . N1 N 0.2619(2) 0.61505(18) 0.0080(2) 0.0312(6) Uani 1 1 d . . . N2 N 0.2199(3) 0.50137(17) 0.2013(2) 0.0299(6) Uani 1 1 d . . . O1 O 0.5621(2) 0.58302(15) 0.04177(19) 0.0342(5) Uani 1 1 d . . . O2 O 0.7206(2) 0.70006(18) 0.0322(2) 0.0548(7) Uani 1 1 d . . . O3 O 0.4794(2) 0.65979(16) 0.2648(2) 0.0437(6) Uani 1 1 d . . . O4 O 0.5067(2) 0.45711(15) 0.2453(2) 0.0396(5) Uani 1 1 d . . . O5 O 0.6624(3) 0.4545(2) 0.4121(2) 0.0685(8) 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 0.0252(2) 0.0325(2) 0.0339(2) 0.00363(16) 0.00719(15) 0.00217(17) C1 0.0345(19) 0.047(2) 0.045(2) 0.0123(16) 0.0121(16) 0.0029(16) C2 0.049(2) 0.057(2) 0.064(3) 0.030(2) 0.0117(19) 0.0089(19) C3 0.044(2) 0.052(2) 0.071(3) 0.022(2) 0.001(2) 0.0171(18) C4 0.0300(19) 0.043(2) 0.056(2) 0.0020(17) 0.0071(16) 0.0074(16) C5 0.0269(17) 0.0298(16) 0.0337(17) -0.0053(13) 0.0047(13) -0.0018(13) C6 0.0282(17) 0.0316(17) 0.0339(17) -0.0084(13) 0.0065(13) -0.0054(13) C7 0.0306(19) 0.047(2) 0.047(2) -0.0079(16) 0.0104(15) -0.0008(15) C8 0.038(2) 0.066(3) 0.049(2) -0.0047(19) 0.0229(17) -0.0108(19) C9 0.053(3) 0.057(2) 0.042(2) 0.0109(17) 0.0164(18) -0.0107(19) C10 0.043(2) 0.046(2) 0.0388(19) 0.0071(15) 0.0068(16) -0.0011(16) C11 0.0246(18) 0.0349(18) 0.0403(19) 0.0053(14) 0.0041(14) 0.0029(14) C12 0.050(2) 0.0354(19) 0.055(2) -0.0040(16) 0.0120(18) -0.0071(17) C13 0.082(3) 0.065(3) 0.035(2) -0.0034(18) 0.010(2) -0.021(2) C14 0.031(2) 0.062(2) 0.036(2) 0.0109(17) 0.0092(16) -0.0028(16) N1 0.0273(15) 0.0325(14) 0.0344(15) 0.0029(11) 0.0052(11) 0.0021(11) N2 0.0283(15) 0.0308(14) 0.0314(14) -0.0011(11) 0.0066(11) -0.0016(11) O1 0.0299(12) 0.0325(12) 0.0417(13) -0.0039(9) 0.0117(10) -0.0013(10) O2 0.0338(14) 0.0572(16) 0.0760(18) 0.0018(13) 0.0202(13) -0.0091(12) O3 0.0462(15) 0.0417(13) 0.0459(14) -0.0063(11) 0.0200(11) -0.0052(11) O4 0.0371(13) 0.0391(13) 0.0423(14) 0.0040(10) 0.0012(11) 0.0066(10) O5 0.0466(17) 0.108(2) 0.0493(16) 0.0241(16) -0.0049(13) 0.0082(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 O4 1.926(2) . ? Cu1 O1 2.000(2) . ? Cu1 N1 2.007(2) . ? Cu1 N2 2.013(3) . ? Cu1 O1 2.346(2) 3_665 ? Cu1 O3 2.411(2) . ? C1 N1 1.339(4) . ? C1 C2 1.374(5) . ? C2 C3 1.368(5) . ? C3 C4 1.366(5) . ? C4 C5 1.379(4) . ? C5 N1 1.351(4) . ? C5 C6 1.479(4) . ? C6 N2 1.347(4) . ? C6 C7 1.388(4) . ? C7 C8 1.381(5) . ? C8 C9 1.369(5) . ? C9 C10 1.375(4) . ? C10 N2 1.338(4) . ? C11 O2 1.219(3) . ? C11 O1 1.279(4) . ? C11 C12 1.520(4) . ? C12 O3 1.410(4) . ? C13 O3 1.419(4) . ? C13 C14 1.515(5) . ? C14 O5 1.227(4) . ? C14 O4 1.269(4) . ? O1 Cu1 2.346(2) 3_665 ? 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 O4 Cu1 O1 91.41(10) . . ? O4 Cu1 N1 171.59(9) . . ? O1 Cu1 N1 94.58(10) . . ? O4 Cu1 N2 92.86(10) . . ? O1 Cu1 N2 171.29(9) . . ? N1 Cu1 N2 80.44(10) . . ? O4 Cu1 O1 90.84(9) . 3_665 ? O1 Cu1 O1 75.28(9) . 3_665 ? N1 Cu1 O1 96.39(9) . 3_665 ? N2 Cu1 O1 112.22(9) . 3_665 ? O4 Cu1 O3 78.63(9) . . ? O1 Cu1 O3 75.75(8) . . ? N1 Cu1 O3 97.11(10) . . ? N2 Cu1 O3 97.66(9) . . ? O1 Cu1 O3 148.84(7) 3_665 . ? N1 C1 C2 121.8(3) . . ? C3 C2 C1 119.0(3) . . ? C4 C3 C2 120.0(3) . . ? C3 C4 C5 118.9(3) . . ? N1 C5 C4 121.4(3) . . ? N1 C5 C6 114.4(3) . . ? C4 C5 C6 124.2(3) . . ? N2 C6 C7 121.6(3) . . ? N2 C6 C5 114.5(3) . . ? C7 C6 C5 123.9(3) . . ? C8 C7 C6 119.1(3) . . ? C9 C8 C7 118.9(3) . . ? C8 C9 C10 119.6(3) . . ? N2 C10 C9 122.2(3) . . ? O2 C11 O1 125.6(3) . . ? O2 C11 C12 117.6(3) . . ? O1 C11 C12 116.8(3) . . ? O3 C12 C11 115.1(3) . . ? O3 C13 C14 116.3(3) . . ? O5 C14 O4 124.3(4) . . ? O5 C14 C13 117.3(3) . . ? O4 C14 C13 118.3(3) . . ? C1 N1 C5 119.0(3) . . ? C1 N1 Cu1 125.6(2) . . ? C5 N1 Cu1 115.27(19) . . ? C10 N2 C6 118.7(3) . . ? C10 N2 Cu1 126.0(2) . . ? C6 N2 Cu1 115.22(19) . . ? C11 O1 Cu1 122.83(19) . . ? C11 O1 Cu1 132.45(18) . 3_665 ? Cu1 O1 Cu1 104.72(9) . 3_665 ? C12 O3 C13 114.5(3) . . ? C12 O3 Cu1 103.55(17) . . ? C13 O3 Cu1 102.39(19) . . ? C14 O4 Cu1 122.3(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.321 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.061