# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Susanne Striegler' 'Moses G. Gichinga' _publ_contact_author_name 'Prof Susanne Striegler' _publ_contact_author_email SUSANNE.STRIEGLER@AUBURN.EDU _publ_section_title ; Disaccharide recognition by binuclear copper(II) complexes ; # Attachment 'Cu2EGbsdpo_B.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 699735' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H30 Cu2 N2 O9' _chemical_formula_sum 'C25 H30 Cu2 N2 O9' _chemical_formula_weight 629.59 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.381(2) _cell_length_b 10.723(4) _cell_length_c 19.732(7) _cell_angle_alpha 94.606(7) _cell_angle_beta 91.898(7) _cell_angle_gamma 107.159(7) _cell_volume 1283.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3677 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 28.31 _exptl_crystal_description rectangular _exptl_crystal_colour green _exptl_crystal_size_max 0.128 _exptl_crystal_size_mid 0.076 _exptl_crystal_size_min 0.024 _exptl_crystal_density_meas nm _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.714 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details SHELXPREP _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 APEX' _diffrn_measurement_method '0.3 wide /w exposures' _diffrn_detector_area_resol_mean ? _diffrn_standards_number na _diffrn_standards_interval_count na _diffrn_standards_interval_time na _diffrn_standards_decay_% 0 _diffrn_reflns_number 13126 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.1178 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6310 _reflns_number_gt 3677 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SMART, SAINT' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2000)' _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^)+(0.0482P)^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 6310 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _refine_ls_shift/su_max 0.002 _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 -1.26031(8) -0.43434(5) 1.18264(2) 0.02544(14) Uani 1 1 d . . . Cu2 Cu -1.60318(8) -0.56665(4) 1.31067(2) 0.02451(14) Uani 1 1 d . . . N1 N -1.0752(5) -0.5437(3) 1.16338(16) 0.0257(8) Uani 1 1 d . . . N2 N -1.5802(5) -0.7395(3) 1.32005(16) 0.0234(7) Uani 1 1 d . . . O1 O -1.6568(4) -0.4044(2) 1.28963(14) 0.0295(7) Uani 1 1 d . . . O2 O -1.4248(5) -0.3161(3) 1.21088(15) 0.0359(8) Uani 1 1 d . . . O3 O -0.7472(5) -0.0199(3) 0.81960(15) 0.0393(8) Uani 1 1 d . . . O4 O -0.6699(5) -0.1348(3) 0.94406(14) 0.0363(7) Uani 1 1 d . . . O5 O -1.1376(5) -0.3183(3) 1.11681(14) 0.0338(7) Uani 1 1 d . . . O6 O -1.4002(4) -0.5646(2) 1.24070(14) 0.0277(7) Uani 1 1 d . . . O7 O -1.8181(4) -0.5817(2) 1.37591(14) 0.0259(6) Uani 1 1 d . . . O8 O -2.4170(4) -0.7939(2) 1.50466(14) 0.0317(7) Uani 1 1 d . . . O9 O -2.7099(5) -0.6016(3) 1.59554(14) 0.0331(7) Uani 1 1 d . . . C1 C -1.6586(8) -0.2003(4) 1.2550(2) 0.0454(13) Uani 1 1 d . . . H1A H -1.7704 -0.2105 1.2887 0.068 Uiso 1 1 calc R . . H1B H -1.7241 -0.1944 1.2102 0.068 Uiso 1 1 calc R . . H1C H -1.5377 -0.1201 1.2681 0.068 Uiso 1 1 calc R . . C2 C -1.5724(7) -0.3161(4) 1.2519(2) 0.0294(10) Uani 1 1 d . . . C3 C -0.9412(9) 0.0012(5) 0.7951(3) 0.0592(15) Uani 1 1 d . . . H3A H -0.9894 -0.0494 0.7508 0.089 Uiso 1 1 calc R . . H3B H -0.9143 0.0947 0.7899 0.089 Uiso 1 1 calc R . . H3C H -1.0557 -0.0269 0.8273 0.089 Uiso 1 1 calc R . . C4 C -0.6688(7) 0.0484(4) 0.8841(2) 0.0320(10) Uani 1 1 d . . . H4A H -0.7056 0.1320 0.8876 0.038 Uiso 1 1 calc R . . H4B H -0.5068 0.0694 0.8883 0.038 Uiso 1 1 calc R . . C5 C -0.7662(7) -0.0300(4) 0.9417(2) 0.0329(10) Uani 1 1 d . . . H5A H -0.7332 0.0264 0.9853 0.040 Uiso 1 1 calc R . . H5B H -0.9277 -0.0656 0.9337 0.040 Uiso 1 1 calc R . . C6 C -0.7423(7) -0.2245(4) 0.9900(2) 0.0292(10) Uani 1 1 d . . . C7 C -0.6260(7) -0.3169(4) 0.9929(2) 0.0318(10) Uani 1 1 d . . . H7A H -0.5082 -0.3146 0.9643 0.038 Uiso 1 1 calc R . . C8 C -0.6861(7) -0.4102(4) 1.0378(2) 0.0348(11) Uani 1 1 d . . . H8A H -0.6069 -0.4723 1.0403 0.042 Uiso 1 1 calc R . . C9 C -0.8601(6) -0.4175(4) 1.0800(2) 0.0261(9) Uani 1 1 d . . . C10 C -0.9755(7) -0.3230(4) 1.0781(2) 0.0278(10) Uani 1 1 d . . . C11 C -0.9128(7) -0.2268(4) 1.0316(2) 0.0303(10) Uani 1 1 d . . . H11A H -0.9887 -0.1632 1.0289 0.036 Uiso 1 1 calc R . . C12 C -0.9159(7) -0.5232(4) 1.1230(2) 0.0290(10) Uani 1 1 d . . . H12A H -0.8297 -0.5820 1.1216 0.035 Uiso 1 1 calc R . . C13 C -1.1238(7) -0.6572(4) 1.2030(2) 0.0349(11) Uani 1 1 d . . . H13A H -1.1395 -0.7374 1.1723 0.042 Uiso 1 1 calc R . . H13B H -1.0002 -0.6470 1.2367 0.042 Uiso 1 1 calc R . . C14 C -1.3191(12) -0.6705(6) 1.2372(4) 0.121(4) Uani 1 1 d . . . H14A H -1.4187 -0.7187 1.1972 0.145 Uiso 1 1 calc R . . C15 C -1.4036(7) -0.7687(4) 1.2824(2) 0.0290(10) Uani 1 1 d . . . H15A H -1.2841 -0.7722 1.3148 0.035 Uiso 1 1 calc R . . H15B H -1.4608 -0.8555 1.2559 0.035 Uiso 1 1 calc R . . C16 C -1.7113(6) -0.8281(4) 1.35224(19) 0.0233(9) Uani 1 1 d . . . H16A H -1.6873 -0.9116 1.3505 0.028 Uiso 1 1 calc R . . C17 C -1.8897(6) -0.8112(4) 1.3903(2) 0.0244(9) Uani 1 1 d . . . C18 C -1.9316(6) -0.6893(4) 1.4021(2) 0.0252(9) Uani 1 1 d . . . C19 C -2.1086(6) -0.6819(4) 1.4418(2) 0.0231(9) Uani 1 1 d . . . H19A H -2.1365 -0.6001 1.4510 0.028 Uiso 1 1 calc R . . C20 C -2.2410(6) -0.7920(4) 1.4673(2) 0.0246(9) Uani 1 1 d . . . C21 C -2.2049(7) -0.9139(4) 1.4539(2) 0.0297(10) Uani 1 1 d . . . H21A H -2.3006 -0.9901 1.4700 0.036 Uiso 1 1 calc R . . C22 C -2.0307(7) -0.9219(4) 1.4174(2) 0.0289(10) Uani 1 1 d . . . H22A H -2.0031 -1.0042 1.4099 0.035 Uiso 1 1 calc R . . C23 C -2.4626(7) -0.6731(4) 1.5243(2) 0.0282(10) Uani 1 1 d . . . H23A H -2.5003 -0.6331 1.4839 0.034 Uiso 1 1 calc R . . H23B H -2.3352 -0.6098 1.5505 0.034 Uiso 1 1 calc R . . C24 C -2.6558(7) -0.7139(4) 1.5678(2) 0.0290(10) Uani 1 1 d . . . H24A H -2.7835 -0.7735 1.5400 0.035 Uiso 1 1 calc R . . H24B H -2.6195 -0.7618 1.6052 0.035 Uiso 1 1 calc R . . C25 C -2.9064(7) -0.6424(4) 1.6311(2) 0.0378(11) Uani 1 1 d . . . H25A H -2.9443 -0.5652 1.6501 0.057 Uiso 1 1 calc R . . H25B H -2.8833 -0.6937 1.6680 0.057 Uiso 1 1 calc R . . H25C H -3.0265 -0.6965 1.5995 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 0.0273(3) 0.0247(3) 0.0282(3) 0.0068(2) 0.0118(2) 0.0114(2) Cu2 0.0251(3) 0.0209(3) 0.0300(3) 0.0061(2) 0.0124(2) 0.0086(2) N1 0.029(2) 0.0274(18) 0.0250(19) 0.0047(15) 0.0092(16) 0.0136(15) N2 0.0241(19) 0.0182(16) 0.0296(19) 0.0039(14) 0.0085(15) 0.0076(14) O1 0.0317(17) 0.0247(15) 0.0402(18) 0.0137(13) 0.0177(14) 0.0161(13) O2 0.0418(19) 0.0346(17) 0.0425(19) 0.0142(14) 0.0239(15) 0.0237(14) O3 0.055(2) 0.0310(16) 0.0341(19) 0.0028(14) 0.0056(16) 0.0164(15) O4 0.0405(19) 0.0394(17) 0.0363(18) 0.0148(14) 0.0188(15) 0.0185(15) O5 0.0386(18) 0.0351(16) 0.0400(18) 0.0158(14) 0.0221(15) 0.0247(14) O6 0.0305(16) 0.0250(15) 0.0337(16) 0.0086(12) 0.0167(13) 0.0144(13) O7 0.0264(15) 0.0176(13) 0.0357(16) 0.0035(12) 0.0154(13) 0.0081(12) O8 0.0330(17) 0.0203(14) 0.0428(18) 0.0044(13) 0.0211(14) 0.0070(13) O9 0.0313(17) 0.0315(16) 0.0417(18) 0.0087(14) 0.0185(14) 0.0142(13) C1 0.055(3) 0.039(3) 0.059(3) 0.026(2) 0.037(3) 0.030(2) C2 0.027(2) 0.028(2) 0.037(3) 0.0061(19) 0.008(2) 0.0121(19) C3 0.066(4) 0.051(3) 0.057(4) -0.001(3) -0.013(3) 0.014(3) C4 0.034(3) 0.030(2) 0.034(3) 0.008(2) 0.007(2) 0.011(2) C5 0.037(3) 0.032(2) 0.033(3) 0.0093(19) 0.011(2) 0.012(2) C6 0.032(2) 0.028(2) 0.029(2) 0.0063(18) 0.0108(19) 0.0098(19) C7 0.030(2) 0.037(2) 0.034(2) 0.006(2) 0.016(2) 0.016(2) C8 0.040(3) 0.032(2) 0.042(3) 0.013(2) 0.020(2) 0.021(2) C9 0.025(2) 0.027(2) 0.029(2) 0.0034(18) 0.0088(18) 0.0091(18) C10 0.028(2) 0.025(2) 0.032(2) 0.0027(18) 0.0077(19) 0.0091(18) C11 0.030(2) 0.033(2) 0.031(2) 0.0065(19) 0.0067(19) 0.013(2) C12 0.029(2) 0.028(2) 0.035(3) 0.0047(19) 0.010(2) 0.0140(19) C13 0.033(3) 0.035(2) 0.044(3) 0.021(2) 0.015(2) 0.015(2) C14 0.153(7) 0.075(4) 0.203(8) 0.104(5) 0.158(7) 0.098(5) C15 0.028(2) 0.031(2) 0.034(2) 0.0103(19) 0.0138(19) 0.0143(19) C16 0.025(2) 0.0189(19) 0.025(2) -0.0013(16) 0.0042(17) 0.0065(17) C17 0.024(2) 0.019(2) 0.029(2) 0.0023(17) 0.0106(18) 0.0046(17) C18 0.024(2) 0.019(2) 0.030(2) 0.0010(17) 0.0075(18) 0.0013(17) C19 0.024(2) 0.0162(19) 0.031(2) 0.0023(16) 0.0106(18) 0.0082(16) C20 0.021(2) 0.024(2) 0.028(2) 0.0020(17) 0.0096(18) 0.0045(17) C21 0.034(3) 0.020(2) 0.034(2) 0.0073(18) 0.015(2) 0.0037(18) C22 0.033(2) 0.017(2) 0.037(3) 0.0030(18) 0.009(2) 0.0065(18) C23 0.029(2) 0.023(2) 0.033(2) 0.0003(18) 0.0138(19) 0.0074(18) C24 0.028(2) 0.025(2) 0.034(2) 0.0047(18) 0.0102(19) 0.0086(18) C25 0.026(2) 0.050(3) 0.041(3) 0.001(2) 0.011(2) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O5 1.897(3) . ? Cu1 O6 1.910(3) . ? Cu1 N1 1.921(3) . ? Cu1 O2 1.931(3) . ? Cu2 O7 1.893(2) . ? Cu2 O6 1.921(2) . ? Cu2 N2 1.925(3) . ? Cu2 O1 1.942(3) . ? N1 C12 1.291(5) . ? N1 C13 1.461(5) . ? N2 C16 1.292(4) . ? N2 C15 1.465(4) . ? O1 C2 1.258(5) . ? O2 C2 1.261(4) . ? O3 C3 1.401(6) . ? O3 C4 1.413(5) . ? O4 C6 1.365(4) . ? O4 C5 1.435(5) . ? O5 C10 1.316(4) . ? O6 C14 1.378(5) . ? O7 C18 1.323(4) . ? O8 C20 1.359(4) . ? O8 C23 1.436(4) . ? O9 C24 1.422(4) . ? O9 C25 1.428(5) . ? C1 C2 1.497(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.509(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.380(5) . ? C6 C7 1.406(5) . ? C7 C8 1.368(5) . ? C7 H7A 0.9500 . ? C8 C9 1.398(5) . ? C8 H8A 0.9500 . ? C9 C10 1.419(5) . ? C9 C12 1.438(5) . ? C10 C11 1.414(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.412(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.429(6) . ? C14 H14A 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.432(5) . ? C16 H16A 0.9500 . ? C17 C18 1.412(5) . ? C17 C22 1.417(5) . ? C18 C19 1.414(5) . ? C19 C20 1.377(5) . ? C19 H19A 0.9500 . ? C20 C21 1.399(5) . ? C21 C22 1.364(5) . ? C21 H21A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.503(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 O5 Cu1 O6 173.68(13) . . ? O5 Cu1 N1 93.56(12) . . ? O6 Cu1 N1 84.77(12) . . ? O5 Cu1 O2 87.79(11) . . ? O6 Cu1 O2 94.54(11) . . ? N1 Cu1 O2 173.61(14) . . ? O7 Cu2 O6 175.31(12) . . ? O7 Cu2 N2 93.30(12) . . ? O6 Cu2 N2 83.90(12) . . ? O7 Cu2 O1 87.64(11) . . ? O6 Cu2 O1 94.58(11) . . ? N2 Cu2 O1 171.43(13) . . ? C12 N1 C13 120.1(3) . . ? C12 N1 Cu1 127.1(3) . . ? C13 N1 Cu1 112.7(2) . . ? C16 N2 C15 120.6(3) . . ? C16 N2 Cu2 125.7(3) . . ? C15 N2 Cu2 113.6(2) . . ? C2 O1 Cu2 135.0(3) . . ? C2 O2 Cu1 136.1(3) . . ? C3 O3 C4 112.9(3) . . ? C6 O4 C5 118.3(3) . . ? C10 O5 Cu1 127.1(3) . . ? C14 O6 Cu1 113.1(2) . . ? C14 O6 Cu2 113.9(3) . . ? Cu1 O6 Cu2 132.45(14) . . ? C18 O7 Cu2 127.5(2) . . ? C20 O8 C23 119.4(3) . . ? C24 O9 C25 109.3(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 126.6(4) . . ? O1 C2 C1 116.7(3) . . ? O2 C2 C1 116.7(3) . . ? O3 C3 H3A 109.5 . . ? O3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O3 C4 C5 112.2(4) . . ? O3 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? O3 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O4 C5 C4 107.4(3) . . ? O4 C5 H5A 110.2 . . ? C4 C5 H5A 110.2 . . ? O4 C5 H5B 110.2 . . ? C4 C5 H5B 110.2 . . ? H5A C5 H5B 108.5 . . ? O4 C6 C11 124.6(4) . . ? O4 C6 C7 114.4(3) . . ? C11 C6 C7 121.1(4) . . ? C8 C7 C6 118.5(4) . . ? C8 C7 H7A 120.7 . . ? C6 C7 H7A 120.7 . . ? C7 C8 C9 122.3(4) . . ? C7 C8 H8A 118.9 . . ? C9 C8 H8A 118.9 . . ? C8 C9 C10 119.3(4) . . ? C8 C9 C12 117.7(4) . . ? C10 C9 C12 123.0(3) . . ? O5 C10 C11 117.4(4) . . ? O5 C10 C9 124.5(4) . . ? C11 C10 C9 118.1(3) . . ? C6 C11 C10 120.6(4) . . ? C6 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? N1 C12 C9 124.4(4) . . ? N1 C12 H12A 117.8 . . ? C9 C12 H12A 117.8 . . ? C14 C13 N1 111.1(4) . . ? C14 C13 H13A 109.4 . . ? N1 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? N1 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O6 C14 C13 116.9(4) . . ? O6 C14 C15 117.0(4) . . ? C13 C14 C15 124.0(4) . . ? O6 C14 H14A 94.8 . . ? C13 C14 H14A 94.8 . . ? C15 C14 H14A 94.8 . . ? C14 C15 N2 110.3(3) . . ? C14 C15 H15A 109.6 . . ? N2 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? N2 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N2 C16 C17 125.6(4) . . ? N2 C16 H16A 117.2 . . ? C17 C16 H16A 117.2 . . ? C18 C17 C22 118.6(3) . . ? C18 C17 C16 123.0(3) . . ? C22 C17 C16 118.4(3) . . ? O7 C18 C17 123.4(3) . . ? O7 C18 C19 117.7(3) . . ? C17 C18 C19 118.8(3) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? O8 C20 C19 124.4(3) . . ? O8 C20 C21 114.8(3) . . ? C19 C20 C21 120.8(3) . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H21A 120.4 . . ? C20 C21 H21A 120.4 . . ? C21 C22 C17 121.9(4) . . ? C21 C22 H22A 119.1 . . ? C17 C22 H22A 119.1 . . ? O8 C23 C24 103.6(3) . . ? O8 C23 H23A 111.0 . . ? C24 C23 H23A 111.0 . . ? O8 C23 H23B 111.0 . . ? C24 C23 H23B 111.0 . . ? H23A C23 H23B 109.0 . . ? O9 C24 C23 110.0(3) . . ? O9 C24 H24A 109.7 . . ? C23 C24 H24A 109.7 . . ? O9 C24 H24B 109.7 . . ? C23 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? O9 C25 H25A 109.5 . . ? O9 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O9 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 N1 C12 5.8(4) . . . . ? O6 Cu1 N1 C12 179.7(4) . . . . ? O2 Cu1 N1 C12 -96.2(11) . . . . ? O5 Cu1 N1 C13 -177.1(3) . . . . ? O6 Cu1 N1 C13 -3.2(3) . . . . ? O2 Cu1 N1 C13 80.8(12) . . . . ? O7 Cu2 N2 C16 10.9(3) . . . . ? O6 Cu2 N2 C16 -165.3(4) . . . . ? O1 Cu2 N2 C16 -85.1(9) . . . . ? O7 Cu2 N2 C15 -173.2(3) . . . . ? O6 Cu2 N2 C15 10.6(3) . . . . ? O1 Cu2 N2 C15 90.7(8) . . . . ? O7 Cu2 O1 C2 174.9(4) . . . . ? O6 Cu2 O1 C2 -9.2(4) . . . . ? N2 Cu2 O1 C2 -88.6(9) . . . . ? O5 Cu1 O2 C2 174.1(4) . . . . ? O6 Cu1 O2 C2 0.0(4) . . . . ? N1 Cu1 O2 C2 -83.5(12) . . . . ? O6 Cu1 O5 C10 -77.0(11) . . . . ? N1 Cu1 O5 C10 -2.6(4) . . . . ? O2 Cu1 O5 C10 171.2(4) . . . . ? O5 Cu1 O6 C14 70.6(12) . . . . ? N1 Cu1 O6 C14 -4.3(5) . . . . ? O2 Cu1 O6 C14 -178.0(5) . . . . ? O5 Cu1 O6 Cu2 -118.6(10) . . . . ? N1 Cu1 O6 Cu2 166.5(2) . . . . ? O2 Cu1 O6 Cu2 -7.2(2) . . . . ? O7 Cu2 O6 C14 -61.3(16) . . . . ? N2 Cu2 O6 C14 -7.7(5) . . . . ? O1 Cu2 O6 C14 -179.2(5) . . . . ? O7 Cu2 O6 Cu1 128.0(13) . . . . ? N2 Cu2 O6 Cu1 -178.5(2) . . . . ? O1 Cu2 O6 Cu1 10.0(2) . . . . ? O6 Cu2 O7 C18 40.4(16) . . . . ? N2 Cu2 O7 C18 -12.8(3) . . . . ? O1 Cu2 O7 C18 158.7(3) . . . . ? Cu2 O1 C2 O2 5.2(7) . . . . ? Cu2 O1 C2 C1 -175.9(3) . . . . ? Cu1 O2 C2 O1 1.0(8) . . . . ? Cu1 O2 C2 C1 -177.9(3) . . . . ? C3 O3 C4 C5 88.2(4) . . . . ? C6 O4 C5 C4 -176.2(4) . . . . ? O3 C4 C5 O4 71.5(4) . . . . ? C5 O4 C6 C11 4.5(6) . . . . ? C5 O4 C6 C7 -174.7(4) . . . . ? O4 C6 C7 C8 179.6(4) . . . . ? C11 C6 C7 C8 0.3(7) . . . . ? C6 C7 C8 C9 0.7(7) . . . . ? C7 C8 C9 C10 -1.8(7) . . . . ? C7 C8 C9 C12 177.2(4) . . . . ? Cu1 O5 C10 C11 179.1(3) . . . . ? Cu1 O5 C10 C9 -1.0(6) . . . . ? C8 C9 C10 O5 -178.1(4) . . . . ? C12 C9 C10 O5 3.0(7) . . . . ? C8 C9 C10 C11 1.8(6) . . . . ? C12 C9 C10 C11 -177.1(4) . . . . ? O4 C6 C11 C10 -179.5(4) . . . . ? C7 C6 C11 C10 -0.3(7) . . . . ? O5 C10 C11 C6 179.1(4) . . . . ? C9 C10 C11 C6 -0.8(6) . . . . ? C13 N1 C12 C9 177.6(4) . . . . ? Cu1 N1 C12 C9 -5.6(6) . . . . ? C8 C9 C12 N1 -178.4(4) . . . . ? C10 C9 C12 N1 0.5(7) . . . . ? C12 N1 C13 C14 -172.8(6) . . . . ? Cu1 N1 C13 C14 9.9(6) . . . . ? Cu1 O6 C14 C13 11.6(9) . . . . ? Cu2 O6 C14 C13 -161.0(5) . . . . ? Cu1 O6 C14 C15 175.9(5) . . . . ? Cu2 O6 C14 C15 3.3(9) . . . . ? N1 C13 C14 O6 -14.0(9) . . . . ? N1 C13 C14 C15 -177.0(7) . . . . ? O6 C14 C15 N2 5.2(9) . . . . ? C13 C14 C15 N2 168.2(7) . . . . ? C16 N2 C15 C14 164.8(5) . . . . ? Cu2 N2 C15 C14 -11.3(6) . . . . ? C15 N2 C16 C17 -179.6(4) . . . . ? Cu2 N2 C16 C17 -4.0(6) . . . . ? N2 C16 C17 C18 -5.7(7) . . . . ? N2 C16 C17 C22 174.2(4) . . . . ? Cu2 O7 C18 C17 7.6(6) . . . . ? Cu2 O7 C18 C19 -170.0(3) . . . . ? C22 C17 C18 O7 -176.0(4) . . . . ? C16 C17 C18 O7 3.9(6) . . . . ? C22 C17 C18 C19 1.6(6) . . . . ? C16 C17 C18 C19 -178.4(4) . . . . ? O7 C18 C19 C20 176.3(4) . . . . ? C17 C18 C19 C20 -1.5(6) . . . . ? C23 O8 C20 C19 -5.1(6) . . . . ? C23 O8 C20 C21 176.9(4) . . . . ? C18 C19 C20 O8 -178.6(4) . . . . ? C18 C19 C20 C21 -0.7(6) . . . . ? O8 C20 C21 C22 -179.3(4) . . . . ? C19 C20 C21 C22 2.7(6) . . . . ? C20 C21 C22 C17 -2.5(7) . . . . ? C18 C17 C22 C21 0.3(6) . . . . ? C16 C17 C22 C21 -179.6(4) . . . . ? C20 O8 C23 C24 -176.4(4) . . . . ? C25 O9 C24 C23 174.3(4) . . . . ? O8 C23 C24 O9 175.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.809 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.098 # Attachment 'Cu2bpdbo_B.cif' data_save _database_code_depnum_ccdc_archive 'CCDC 699736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Cl Cu2 N4 O8, Cl O4' _chemical_formula_sum 'C18 H24 Cl2 Cu2 N4 O12' _chemical_formula_weight 686.41 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' Cl Cl 0.1484 0.1585 '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' _symmetry_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 15.0763(17) _cell_length_b 12.2502(14) _cell_length_c 15.3221(18) _cell_angle_alpha 90.00 _cell_angle_beta 116.020(2) _cell_angle_gamma 90.00 _cell_volume 2543.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4539 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.34 _exptl_crystal_description Platelet _exptl_crystal_colour Blue _exptl_crystal_size_max 0.304 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.168 _exptl_crystal_density_meas nm _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.951 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5671 _exptl_absorpt_correction_T_max 0.7155 _exptl_absorpt_process_details SHELXPREP _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 APEX' _diffrn_measurement_method '0.3 wide /w exposures' _diffrn_detector_area_resol_mean ? _diffrn_standards_number na _diffrn_standards_interval_count na _diffrn_standards_interval_time na _diffrn_standards_decay_% 0 _diffrn_reflns_number 24008 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6303 _reflns_number_gt 4539 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SMART, SAINT' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXS-97 (Sheldrick, 2000)' _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^)+(0.1193P)^2^+3.1883P] 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 SHELXL _refine_ls_extinction_coef 0 _refine_ls_number_reflns 6303 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1830 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 Cl2 Cl -0.08792(9) 0.47279(9) 0.33548(8) 0.0376(3) Uani 1 1 d . . . O8 O -0.0154(3) 0.4069(3) 0.4089(3) 0.0626(12) Uani 1 1 d . . . O7 O -0.1593(4) 0.5148(5) 0.3646(4) 0.0765(15) Uani 1 1 d . . . O6 O -0.0408(3) 0.5660(4) 0.3173(4) 0.0667(12) Uani 1 1 d . . . O5 O -0.1367(4) 0.4094(4) 0.2497(3) 0.0766(15) Uani 1 1 d . . . Cu1 Cu 0.32331(4) 0.51714(5) 0.23731(4) 0.03108(17) Uani 1 1 d . . . Cu2 Cu 0.46043(4) 0.59669(4) 0.12270(4) 0.03145(17) Uani 1 1 d . . . N2 N 0.3169(3) 0.4786(3) 0.3618(3) 0.0318(8) Uani 1 1 d . . . N4 N 0.5674(3) 0.6214(3) 0.0809(3) 0.0330(8) Uani 1 1 d . . . N3 N 0.3911(3) 0.7053(3) 0.0188(3) 0.0396(9) Uani 1 1 d . . . H3AA H 0.4015 0.7736 0.0482 0.048 Uiso 1 1 calc R . . N1 N 0.1865(3) 0.5676(4) 0.2016(3) 0.0426(10) Uani 1 1 d . . . H1B H 0.1548 0.5024 0.1743 0.051 Uiso 1 1 calc R . . C18 C 0.5110(3) 0.4141(3) 0.2573(3) 0.0289(8) Uani 1 1 d . . . C12 C 0.5399(4) 0.6820(4) 0.0002(3) 0.0365(10) Uani 1 1 d . . . C4 C 0.2213(4) 0.5027(4) 0.4494(4) 0.0386(10) Uani 1 1 d . . . H4A H 0.1617 0.5258 0.4506 0.046 Uiso 1 1 calc R . . C2 C 0.3818(4) 0.4230(4) 0.5265(3) 0.0378(10) Uani 1 1 d . . . H2A H 0.4348 0.3923 0.5817 0.045 Uiso 1 1 calc R . . C5 C 0.2340(3) 0.5135(4) 0.3666(3) 0.0340(9) Uani 1 1 d . . . C10 C 0.2860(4) 0.6808(4) -0.0182(3) 0.0408(11) Uani 1 1 d . . . H10B H 0.2687 0.6159 -0.0610 0.049 Uiso 1 1 calc R . . H10A H 0.2460 0.7434 -0.0560 0.049 Uiso 1 1 calc R . . C3 C 0.2974(4) 0.4574(4) 0.5320(3) 0.0380(10) Uani 1 1 d . . . H3A H 0.2910 0.4504 0.5907 0.046 Uiso 1 1 calc R . . C17 C 0.5801(3) 0.3216(4) 0.3056(3) 0.0377(10) Uani 1 1 d . . . H17C H 0.6327 0.3207 0.2844 0.057 Uiso 1 1 calc R . . H17B H 0.5437 0.2525 0.2878 0.057 Uiso 1 1 calc R . . H17A H 0.6090 0.3311 0.3762 0.057 Uiso 1 1 calc R . . C16 C 0.6625(4) 0.5932(4) 0.1311(4) 0.0369(10) Uani 1 1 d . . . H16A H 0.6815 0.5518 0.1890 0.044 Uiso 1 1 calc R . . C1 C 0.3883(3) 0.4339(4) 0.4395(3) 0.0337(9) Uani 1 1 d . . . H1A H 0.4459 0.4083 0.4355 0.040 Uiso 1 1 calc R . . C15 C 0.7334(4) 0.6220(4) 0.1020(4) 0.0428(11) Uani 1 1 d . . . H15A H 0.8001 0.5998 0.1380 0.051 Uiso 1 1 calc R . . C13 C 0.6076(4) 0.7152(4) -0.0327(4) 0.0436(12) Uani 1 1 d . . . H13A H 0.5872 0.7584 -0.0897 0.052 Uiso 1 1 calc R . . C9 C 0.2663(3) 0.6590(4) 0.0693(3) 0.0400(11) Uani 1 1 d . . . H9A H 0.2792 0.7278 0.1082 0.048 Uiso 1 1 calc R . . C14 C 0.7048(4) 0.6848(5) 0.0181(4) 0.0477(13) Uani 1 1 d . . . H14A H 0.7521 0.7063 -0.0039 0.057 Uiso 1 1 calc R . . C11 C 0.4322(4) 0.7084(4) -0.0508(3) 0.0381(10) Uani 1 1 d . . . H11A H 0.4228 0.7819 -0.0804 0.046 Uiso 1 1 calc R . . H11B H 0.3980 0.6547 -0.1032 0.046 Uiso 1 1 calc R . . C6 C 0.1613(4) 0.5703(5) 0.2777(4) 0.0435(11) Uani 1 1 d . . . H6A H 0.0958 0.5357 0.2569 0.052 Uiso 1 1 calc R . . H6B H 0.1557 0.6473 0.2941 0.052 Uiso 1 1 calc R . . C7 C 0.1298(4) 0.6371(5) 0.1197(4) 0.0504(13) Uani 1 1 d . . . H7A H 0.1378 0.7141 0.1415 0.061 Uiso 1 1 calc R . . H7B H 0.0590 0.6181 0.0940 0.061 Uiso 1 1 calc R . . C8 C 0.1618(4) 0.6257(6) 0.0398(4) 0.0526(14) Uani 1 1 d . . . H8A H 0.1535 0.5487 0.0182 0.063 Uiso 1 1 calc R . . H8B H 0.1181 0.6709 -0.0162 0.063 Uiso 1 1 calc R . . O11 O 0.3351(2) 0.5773(3) 0.1280(2) 0.0327(7) Uani 1 1 d . . . O10 O 0.4396(2) 0.4261(3) 0.2779(2) 0.0386(8) Uani 1 1 d . . . O9 O 0.5297(2) 0.4729(3) 0.2006(2) 0.0355(7) Uani 1 1 d . . . O12 O 0.5325(3) 0.7161(3) 0.2508(3) 0.0471(9) Uani 1 1 d . . . Cl1 Cl 0.37342(8) 0.78216(10) 0.37738(8) 0.0376(3) Uani 1 1 d . . . O4 O 0.4380(3) 0.8699(4) 0.3905(4) 0.0758(14) Uani 1 1 d . . . O1 O 0.2728(3) 0.8168(4) 0.3373(3) 0.0603(11) Uani 1 1 d . . . O3 O 0.3829(4) 0.7047(4) 0.3106(3) 0.0701(13) Uani 1 1 d . . . O2 O 0.3997(3) 0.7263(4) 0.4680(3) 0.0737(14) 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 Cl2 0.0386(6) 0.0402(6) 0.0348(6) 0.0018(5) 0.0168(5) 0.0053(5) O8 0.070(3) 0.047(2) 0.050(2) 0.0110(18) 0.007(2) 0.0141(19) O7 0.057(3) 0.111(4) 0.076(3) -0.008(3) 0.041(3) 0.012(3) O6 0.073(3) 0.057(3) 0.080(3) 0.014(2) 0.043(3) 0.000(2) O5 0.077(3) 0.066(3) 0.049(3) -0.024(2) -0.007(2) 0.019(2) Cu1 0.0271(3) 0.0420(3) 0.0232(3) 0.0029(2) 0.0101(2) 0.0052(2) Cu2 0.0359(3) 0.0342(3) 0.0263(3) 0.0065(2) 0.0154(2) 0.0067(2) N2 0.0303(18) 0.038(2) 0.0286(18) 0.0011(15) 0.0143(15) 0.0007(15) N4 0.042(2) 0.0295(18) 0.0299(19) 0.0009(15) 0.0183(17) -0.0023(16) N3 0.045(2) 0.044(2) 0.032(2) 0.0054(17) 0.0184(18) 0.0050(18) N1 0.037(2) 0.048(2) 0.043(2) 0.0091(19) 0.0184(19) 0.0105(18) C18 0.032(2) 0.031(2) 0.0207(18) -0.0012(16) 0.0088(16) 0.0027(16) C12 0.050(3) 0.030(2) 0.027(2) -0.0051(18) 0.0154(19) -0.006(2) C4 0.040(3) 0.041(3) 0.042(3) -0.005(2) 0.025(2) -0.002(2) C2 0.039(2) 0.044(3) 0.026(2) 0.0009(19) 0.0100(19) -0.005(2) C5 0.030(2) 0.037(2) 0.034(2) -0.0023(18) 0.0134(19) -0.0014(18) C10 0.038(2) 0.046(3) 0.031(2) 0.007(2) 0.0082(19) 0.003(2) C3 0.048(3) 0.043(3) 0.028(2) -0.0037(19) 0.021(2) -0.006(2) C17 0.037(2) 0.043(3) 0.032(2) 0.008(2) 0.0148(19) 0.013(2) C16 0.041(3) 0.035(2) 0.036(2) 0.0024(19) 0.019(2) 0.0018(19) C1 0.033(2) 0.038(2) 0.030(2) -0.0001(18) 0.0130(18) -0.0007(18) C15 0.043(3) 0.044(3) 0.044(3) -0.002(2) 0.022(2) -0.003(2) C13 0.054(3) 0.049(3) 0.029(2) -0.001(2) 0.019(2) -0.011(2) C9 0.037(2) 0.042(3) 0.031(2) 0.004(2) 0.0066(19) 0.013(2) C14 0.053(3) 0.057(3) 0.041(3) -0.007(2) 0.027(2) -0.018(3) C11 0.050(3) 0.038(2) 0.021(2) 0.0019(18) 0.0103(19) -0.009(2) C6 0.033(2) 0.060(3) 0.035(2) 0.005(2) 0.013(2) 0.000(2) C7 0.036(3) 0.066(4) 0.041(3) 0.006(3) 0.009(2) 0.012(2) C8 0.037(3) 0.075(4) 0.037(3) 0.011(3) 0.008(2) 0.002(3) O11 0.0309(15) 0.0401(17) 0.0221(14) 0.0063(12) 0.0070(12) 0.0067(13) O10 0.0348(17) 0.055(2) 0.0292(16) 0.0126(14) 0.0170(14) 0.0154(15) O9 0.0362(17) 0.0358(17) 0.0373(17) 0.0105(14) 0.0187(14) 0.0079(13) O12 0.062(2) 0.046(2) 0.0372(19) -0.0031(15) 0.0253(18) -0.0020(17) Cl1 0.0357(5) 0.0463(6) 0.0277(5) -0.0036(4) 0.0110(4) 0.0030(5) O4 0.043(2) 0.057(3) 0.098(4) 0.005(3) 0.004(2) -0.003(2) O1 0.037(2) 0.079(3) 0.061(3) 0.017(2) 0.0186(18) 0.0100(19) O3 0.093(3) 0.063(3) 0.073(3) -0.034(2) 0.054(3) -0.027(2) O2 0.074(3) 0.105(4) 0.043(2) 0.024(2) 0.027(2) 0.030(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 Cl2 O5 1.423(4) . ? Cl2 O8 1.426(4) . ? Cl2 O7 1.429(4) . ? Cl2 O6 1.435(4) . ? Cu1 O11 1.908(3) . ? Cu1 O10 1.935(3) . ? Cu1 N1 1.987(4) . ? Cu1 N2 2.008(4) . ? Cu2 O9 1.929(3) . ? Cu2 O11 1.941(3) . ? Cu2 N3 1.985(4) . ? Cu2 N4 2.002(4) . ? Cu2 O12 2.303(4) . ? N2 C1 1.324(6) . ? N2 C5 1.353(6) . ? N4 C12 1.342(6) . ? N4 C16 1.342(6) . ? N3 C11 1.450(6) . ? N3 C10 1.460(6) . ? N3 H3AA 0.9300 . ? N1 C6 1.376(6) . ? N1 C7 1.446(7) . ? N1 H1B 0.9300 . ? C18 O9 1.252(5) . ? C18 O10 1.257(5) . ? C18 C17 1.497(6) . ? C12 C13 1.382(7) . ? C12 C11 1.496(7) . ? C4 C5 1.370(7) . ? C4 C3 1.397(7) . ? C4 H4A 0.9500 . ? C2 C3 1.377(7) . ? C2 C1 1.386(6) . ? C2 H2A 0.9500 . ? C5 C6 1.493(7) . ? C10 C9 1.520(7) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C3 H3A 0.9500 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C17 H17A 0.9800 . ? C16 C15 1.373(7) . ? C16 H16A 0.9500 . ? C1 H1A 0.9500 . ? C15 C14 1.394(8) . ? C15 H15A 0.9500 . ? C13 C14 1.375(8) . ? C13 H13A 0.9500 . ? C9 O11 1.439(5) . ? C9 C8 1.492(7) . ? C9 H9A 1.0000 . ? C14 H14A 0.9500 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.505(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? Cl1 O4 1.405(5) . ? Cl1 O1 1.428(4) . ? Cl1 O2 1.439(4) . ? Cl1 O3 1.448(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 O5 Cl2 O8 109.0(3) . . ? O5 Cl2 O7 109.3(3) . . ? O8 Cl2 O7 112.3(3) . . ? O5 Cl2 O6 110.8(3) . . ? O8 Cl2 O6 109.3(3) . . ? O7 Cl2 O6 106.2(3) . . ? O11 Cu1 O10 94.86(13) . . ? O11 Cu1 N1 97.12(15) . . ? O10 Cu1 N1 162.20(17) . . ? O11 Cu1 N2 170.53(15) . . ? O10 Cu1 N2 88.47(14) . . ? N1 Cu1 N2 81.81(17) . . ? O9 Cu2 O11 98.65(13) . . ? O9 Cu2 N3 167.21(16) . . ? O11 Cu2 N3 86.31(15) . . ? O9 Cu2 N4 91.37(14) . . ? O11 Cu2 N4 165.29(14) . . ? N3 Cu2 N4 81.75(16) . . ? O9 Cu2 O12 92.70(14) . . ? O11 Cu2 O12 98.39(13) . . ? N3 Cu2 O12 98.25(16) . . ? N4 Cu2 O12 91.82(14) . . ? C1 N2 C5 119.2(4) . . ? C1 N2 Cu1 126.4(3) . . ? C5 N2 Cu1 114.1(3) . . ? C12 N4 C16 119.4(4) . . ? C12 N4 Cu2 114.4(3) . . ? C16 N4 Cu2 125.8(3) . . ? C11 N3 C10 117.4(4) . . ? C11 N3 Cu2 111.2(3) . . ? C10 N3 Cu2 105.9(3) . . ? C11 N3 H3AA 107.3 . . ? C10 N3 H3AA 107.3 . . ? Cu2 N3 H3AA 107.3 . . ? C6 N1 C7 116.4(4) . . ? C6 N1 Cu1 114.4(3) . . ? C7 N1 Cu1 124.6(3) . . ? C6 N1 H1B 97.1 . . ? C7 N1 H1B 97.1 . . ? Cu1 N1 H1B 97.1 . . ? O9 C18 O10 125.9(4) . . ? O9 C18 C17 117.3(4) . . ? O10 C18 C17 116.8(4) . . ? N4 C12 C13 121.3(5) . . ? N4 C12 C11 115.2(4) . . ? C13 C12 C11 123.5(4) . . ? C5 C4 C3 119.0(4) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C3 C2 C1 119.1(4) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? N2 C5 C4 121.8(4) . . ? N2 C5 C6 115.1(4) . . ? C4 C5 C6 123.0(4) . . ? N3 C10 C9 107.0(4) . . ? N3 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? N3 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? H10B C10 H10A 108.6 . . ? C2 C3 C4 118.6(4) . . ? C2 C3 H3A 120.7 . . ? C4 C3 H3A 120.7 . . ? C18 C17 H17C 109.5 . . ? C18 C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C18 C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? N4 C16 C15 122.4(5) . . ? N4 C16 H16A 118.8 . . ? C15 C16 H16A 118.8 . . ? N2 C1 C2 122.2(4) . . ? N2 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C16 C15 C14 118.1(5) . . ? C16 C15 H15A 120.9 . . ? C14 C15 H15A 120.9 . . ? C14 C13 C12 119.2(5) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? O11 C9 C8 112.1(4) . . ? O11 C9 C10 107.9(4) . . ? C8 C9 C10 111.7(4) . . ? O11 C9 H9A 108.4 . . ? C8 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C13 C14 C15 119.5(5) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? N3 C11 C12 109.1(4) . . ? N3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N1 C6 C5 113.4(4) . . ? N1 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? N1 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N1 C7 C8 111.9(4) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 113.6(5) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C9 O11 Cu1 119.8(3) . . ? C9 O11 Cu2 109.7(3) . . ? Cu1 O11 Cu2 123.46(15) . . ? C18 O10 Cu1 137.8(3) . . ? C18 O9 Cu2 131.0(3) . . ? O4 Cl1 O1 111.9(3) . . ? O4 Cl1 O2 110.3(3) . . ? O1 Cl1 O2 110.3(3) . . ? O4 Cl1 O3 108.9(3) . . ? O1 Cl1 O3 107.9(3) . . ? O2 Cl1 O3 107.5(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.485 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.137