# 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_1 _database_code_depnum_ccdc_archive 'CCDC 886052' #TrackingRef '1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cl2 Cu2 N4 O2' _chemical_formula_weight 584.51 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 11.8586(15) _cell_length_b 11.8952(7) _cell_length_c 18.7920(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.420(14) _cell_angle_gamma 90.00 _cell_volume 2529.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7618 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 30.00 _exptl_crystal_description rectangle _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 1.919 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 7618 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3541 _reflns_number_gt 2552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0758P)^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 3541 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _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 0.37346(3) 0.69026(2) 0.015807(18) 0.01566(10) Uani 1 1 d . . . O11 O 0.23789(15) 0.78040(14) -0.06901(10) 0.0177(4) Uani 1 1 d . . . C12 C 0.2552(2) 0.8352(2) -0.12657(15) 0.0195(5) Uani 1 1 d . . . C13 C 0.1907(3) 0.9327(2) -0.15691(17) 0.0262(6) Uani 1 1 d . . . H13 H 0.1351 0.9610 -0.1356 0.031 Uiso 1 1 calc R . . C14 C 0.2086(3) 0.9867(3) -0.21752(18) 0.0334(7) Uani 1 1 d . . . H14 H 0.1653 1.0507 -0.2370 0.040 Uiso 1 1 calc R . . C15 C 0.2902(3) 0.9459(3) -0.24875(18) 0.0375(8) Uani 1 1 d . . . H15 H 0.3027 0.9815 -0.2898 0.045 Uiso 1 1 calc R . . C16 C 0.3544(3) 0.8508(3) -0.21894(17) 0.0330(7) Uani 1 1 d . . . H16 H 0.4100 0.8241 -0.2408 0.040 Uiso 1 1 calc R . . C17 C 0.3397(2) 0.7935(2) -0.15787(16) 0.0233(6) Uani 1 1 d . . . C18 C 0.4077(2) 0.6880(2) -0.12954(16) 0.0249(6) Uani 1 1 d . . . H18A H 0.4622 0.6746 -0.1582 0.030 Uiso 1 1 calc R . . H18B H 0.3527 0.6254 -0.1386 0.030 Uiso 1 1 calc R . . N19 N 0.47643(18) 0.68941(17) -0.04812(13) 0.0190(5) Uani 1 1 d . . . H19 H 0.5167 0.6232 -0.0390 0.023 Uiso 1 1 calc R . . C20 C 0.5670(2) 0.7796(2) -0.02511(16) 0.0219(6) Uani 1 1 d . . . H20A H 0.5322 0.8517 -0.0438 0.026 Uiso 1 1 calc R . . H20B H 0.6314 0.7650 -0.0457 0.026 Uiso 1 1 calc R . . C21 C 0.6127(2) 0.7823(2) 0.05857(16) 0.0216(6) Uani 1 1 d . . . H21A H 0.6576 0.7146 0.0771 0.026 Uiso 1 1 calc R . . H21B H 0.6640 0.8468 0.0750 0.026 Uiso 1 1 calc R . . N22 N 0.50971(18) 0.78975(17) 0.08685(13) 0.0177(4) Uani 1 1 d . . . Cl1 Cl 0.32391(5) 0.50037(5) -0.01431(4) 0.02495(17) Uani 1 1 d . . . C23 C 0.5453(3) 0.7545(3) 0.16546(17) 0.0334(7) Uani 1 1 d . . . H22A H 0.4783 0.7581 0.1841 0.050 Uiso 1 1 calc R . . H22B H 0.6063 0.8035 0.1942 0.050 Uiso 1 1 calc R . . H22C H 0.5745 0.6787 0.1694 0.050 Uiso 1 1 calc R . . C24 C 0.4658(2) 0.9071(2) 0.08153(17) 0.0256(6) Uani 1 1 d . . . H24A H 0.4027 0.9122 0.1036 0.038 Uiso 1 1 calc R . . H24B H 0.4374 0.9290 0.0301 0.038 Uiso 1 1 calc R . . H24C H 0.5290 0.9562 0.1075 0.038 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 0.01672(16) 0.01081(15) 0.02047(19) -0.00040(12) 0.00715(12) 0.00057(11) O11 0.0195(9) 0.0172(8) 0.0195(10) 0.0040(7) 0.0103(7) 0.0034(7) C12 0.0215(12) 0.0193(12) 0.0171(14) 0.0012(9) 0.0051(10) -0.0044(9) C13 0.0296(14) 0.0214(13) 0.0261(16) 0.0040(11) 0.0060(12) -0.0029(11) C14 0.0379(17) 0.0295(16) 0.0275(18) 0.0102(12) 0.0020(13) -0.0081(13) C15 0.0384(17) 0.046(2) 0.0255(18) 0.0116(14) 0.0063(14) -0.0175(14) C16 0.0279(15) 0.052(2) 0.0225(17) -0.0014(13) 0.0124(12) -0.0105(13) C17 0.0215(13) 0.0328(15) 0.0160(14) -0.0023(11) 0.0060(10) -0.0078(10) C18 0.0227(13) 0.0311(15) 0.0246(16) -0.0102(12) 0.0127(11) -0.0041(11) N19 0.0177(10) 0.0154(10) 0.0252(13) -0.0038(8) 0.0083(9) -0.0003(8) C20 0.0195(12) 0.0188(12) 0.0297(16) -0.0034(10) 0.0110(11) -0.0043(10) C21 0.0162(12) 0.0172(12) 0.0306(16) -0.0030(10) 0.0056(11) 0.0011(9) N22 0.0185(10) 0.0155(10) 0.0192(12) -0.0008(8) 0.0056(8) 0.0003(8) Cl1 0.0206(3) 0.0109(3) 0.0440(4) -0.0038(3) 0.0107(3) 0.0008(2) C23 0.0299(15) 0.0430(19) 0.0238(17) 0.0067(13) 0.0027(12) -0.0081(13) C24 0.0219(13) 0.0161(12) 0.0376(17) -0.0076(11) 0.0072(12) 0.0014(10) _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 O11 1.9118(17) 7_565 ? Cu1 N19 1.953(2) . ? Cu1 N22 2.122(2) . ? Cu1 O11 2.1773(18) . ? Cu1 Cl1 2.3598(7) . ? O11 C12 1.330(3) . ? O11 Cu1 1.9119(17) 7_565 ? C12 C17 1.396(4) . ? C12 C13 1.412(4) . ? C13 C14 1.379(4) . ? C13 H13 0.9300 . ? C14 C15 1.363(5) . ? C14 H14 0.9300 . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.391(4) . ? C16 H16 0.9300 . ? C17 C18 1.500(4) . ? C18 N19 1.503(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N19 C20 1.488(3) . ? N19 H19 0.9100 . ? C20 C21 1.502(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N22 1.474(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? N22 C23 1.471(4) . ? N22 C24 1.483(3) . ? C23 H22A 0.9600 . ? C23 H22B 0.9600 . ? C23 H22C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 O11 Cu1 N19 168.43(8) 7_565 . ? O11 Cu1 N22 94.83(8) 7_565 . ? N19 Cu1 N22 83.76(8) . . ? O11 Cu1 O11 79.55(8) 7_565 . ? N19 Cu1 O11 90.74(8) . . ? N22 Cu1 O11 116.24(8) . . ? O11 Cu1 Cl1 97.98(6) 7_565 . ? N19 Cu1 Cl1 90.24(6) . . ? N22 Cu1 Cl1 140.61(6) . . ? O11 Cu1 Cl1 102.68(5) . . ? C12 O11 Cu1 129.38(16) . 7_565 ? C12 O11 Cu1 125.22(16) . . ? Cu1 O11 Cu1 100.45(8) 7_565 . ? O11 C12 C17 118.2(2) . . ? O11 C12 C13 122.3(3) . . ? C17 C12 C13 119.5(3) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 123.0(3) . . ? C15 C16 H16 118.5 . . ? C17 C16 H16 118.5 . . ? C16 C17 C12 117.2(3) . . ? C16 C17 C18 121.1(3) . . ? C12 C17 C18 121.7(2) . . ? C17 C18 N19 115.0(2) . . ? C17 C18 H18A 108.5 . . ? N19 C18 H18A 108.5 . . ? C17 C18 H18B 108.5 . . ? N19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 N19 C18 115.4(2) . . ? C20 N19 Cu1 110.32(16) . . ? C18 N19 Cu1 112.20(15) . . ? C20 N19 H19 106.1 . . ? C18 N19 H19 106.1 . . ? Cu1 N19 H19 106.1 . . ? N19 C20 C21 108.8(2) . . ? N19 C20 H20A 109.9 . . ? C21 C20 H20A 109.9 . . ? N19 C20 H20B 109.9 . . ? C21 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? N22 C21 C20 107.5(2) . . ? N22 C21 H21A 110.2 . . ? C20 C21 H21A 110.2 . . ? N22 C21 H21B 110.2 . . ? C20 C21 H21B 110.2 . . ? H21A C21 H21B 108.5 . . ? C23 N22 C21 109.0(2) . . ? C23 N22 C24 109.0(2) . . ? C21 N22 C24 110.2(2) . . ? C23 N22 Cu1 114.09(17) . . ? C21 N22 Cu1 107.27(16) . . ? C24 N22 Cu1 107.28(16) . . ? N22 C23 H22A 109.5 . . ? N22 C23 H22B 109.5 . . ? H22A C23 H22B 109.5 . . ? N22 C23 H22C 109.5 . . ? H22A C23 H22C 109.5 . . ? H22B C23 H22C 109.5 . . ? N22 C24 H24A 109.5 . . ? N22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 1.313 _refine_diff_density_min -1.149 _refine_diff_density_rms 0.119 data_2 _database_code_depnum_ccdc_archive 'CCDC 886053' #TrackingRef '1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Cl2 Cu2 N4 O3' _chemical_formula_weight 602.52 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.359(6) _cell_length_b 7.7866(12) _cell_length_c 17.511(5) _cell_angle_alpha 90.00 _cell_angle_beta 130.06(4) _cell_angle_gamma 90.00 _cell_volume 2646.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7249 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 30.00 _exptl_crystal_description rectangle _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 1.839 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 7249 _diffrn_reflns_av_R_equivalents 0.0781 _diffrn_reflns_av_sigmaI/netI 0.1375 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3626 _reflns_number_gt 2136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0251P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3626 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 -0.03704(2) 0.08605(8) 0.13814(4) 0.02401(17) Uani 1 1 d . . . Cl2 Cl -0.05747(6) -0.18658(17) 0.04933(10) 0.0368(3) Uani 1 1 d . . . O11 O 0.05493(14) 0.0492(4) 0.2696(2) 0.0266(8) Uani 1 1 d . . . C12 C 0.1109(2) 0.0150(7) 0.2780(4) 0.0288(11) Uani 1 1 d . . . C13 C 0.1533(2) -0.1244(7) 0.3338(4) 0.0376(14) Uani 1 1 d . . . H13 H 0.1441 -0.1948 0.3669 0.045 Uiso 1 1 calc R . . C14 C 0.2101(2) -0.1573(8) 0.3396(4) 0.0456(16) Uani 1 1 d . . . H14 H 0.2390 -0.2493 0.3774 0.055 Uiso 1 1 calc R . . C15 C 0.2234(2) -0.0550(8) 0.2902(4) 0.0452(17) Uani 1 1 d . . . H15 H 0.2611 -0.0780 0.2944 0.054 Uiso 1 1 calc R . . C16 C 0.1813(2) 0.0809(7) 0.2347(4) 0.0363(13) Uani 1 1 d . . . H16 H 0.1906 0.1487 0.2009 0.044 Uiso 1 1 calc R . . C17 C 0.1247(2) 0.1195(7) 0.2279(4) 0.0290(12) Uani 1 1 d . . . C18 C 0.0777(2) 0.2674(6) 0.1670(4) 0.0288(11) Uani 1 1 d . . . H18A H 0.0782 0.3476 0.2098 0.035 Uiso 1 1 calc R . . H18B H 0.0937 0.3273 0.1368 0.035 Uiso 1 1 calc R . . N19 N 0.00581(16) 0.2042(5) 0.0872(3) 0.0253(9) Uani 1 1 d . . . H19 H 0.0079 0.1254 0.0508 0.030 Uiso 1 1 calc R . . C20 C -0.0416(2) 0.3399(7) 0.0179(4) 0.0322(12) Uani 1 1 d . . . H20A H -0.0326 0.3699 -0.0266 0.039 Uiso 1 1 calc R . . H20B H -0.0357 0.4419 0.0545 0.039 Uiso 1 1 calc R . . C21 C -0.1137(2) 0.2714(7) -0.0409(3) 0.0306(12) Uani 1 1 d . . . H21A H -0.1464 0.3610 -0.0844 0.037 Uiso 1 1 calc R . . H21B H -0.1204 0.1769 -0.0825 0.037 Uiso 1 1 calc R . . N22 N -0.12724(17) 0.2114(5) 0.0248(3) 0.0284(10) Uani 1 1 d . . . C23 C -0.1383(2) 0.3598(7) 0.0665(4) 0.0402(14) Uani 1 1 d . . . H23A H -0.0975 0.4292 0.1060 0.060 Uiso 1 1 calc R . . H23B H -0.1484 0.3186 0.1076 0.060 Uiso 1 1 calc R . . H23C H -0.1763 0.4275 0.0129 0.060 Uiso 1 1 calc R . . C24 C -0.1901(2) 0.1038(7) -0.0339(4) 0.0389(14) Uani 1 1 d . . . H24A H -0.2286 0.1709 -0.0871 0.058 Uiso 1 1 calc R . . H24B H -0.1990 0.0632 0.0086 0.058 Uiso 1 1 calc R . . H24C H -0.1836 0.0076 -0.0614 0.058 Uiso 1 1 calc R . . O1 O 0.0000 -0.4015(8) 0.2500 0.065(2) Uani 1 2 d S . . H1 H 0.013(4) -0.339(8) 0.293(5) 0.077 Uiso 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 0.0229(3) 0.0260(4) 0.0261(3) 0.0003(3) 0.0170(2) 0.0002(2) Cl2 0.0529(7) 0.0271(8) 0.0406(7) -0.0071(6) 0.0347(7) -0.0045(6) O11 0.0252(15) 0.033(2) 0.0277(17) 0.0048(15) 0.0197(14) 0.0057(13) C12 0.027(2) 0.036(3) 0.027(2) -0.007(2) 0.019(2) 0.001(2) C13 0.028(2) 0.041(4) 0.035(3) 0.005(3) 0.017(2) 0.007(2) C14 0.026(2) 0.046(4) 0.042(3) -0.009(3) 0.012(3) 0.009(2) C15 0.026(2) 0.064(5) 0.046(4) -0.021(3) 0.023(3) -0.006(3) C16 0.030(2) 0.047(4) 0.042(3) -0.010(3) 0.028(2) -0.010(2) C17 0.024(2) 0.037(3) 0.027(2) -0.011(2) 0.017(2) -0.001(2) C18 0.030(2) 0.031(3) 0.029(3) -0.002(2) 0.021(2) -0.006(2) N19 0.0230(17) 0.022(2) 0.026(2) -0.0060(18) 0.0138(17) -0.0041(15) C20 0.039(3) 0.025(3) 0.041(3) 0.005(2) 0.029(2) -0.002(2) C21 0.030(2) 0.038(3) 0.024(3) 0.006(2) 0.018(2) -0.001(2) N22 0.0238(18) 0.034(3) 0.027(2) -0.0031(19) 0.0161(17) -0.0033(17) C23 0.039(3) 0.044(4) 0.040(3) 0.004(3) 0.027(3) 0.011(2) C24 0.025(2) 0.051(4) 0.031(3) -0.001(3) 0.014(2) -0.006(2) O1 0.086(5) 0.030(4) 0.039(4) 0.000 0.022(4) 0.000 _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 O11 1.961(3) 2 ? Cu1 O11 1.977(3) . ? Cu1 N19 2.017(4) . ? Cu1 N22 2.069(4) . ? Cu1 Cl2 2.4812(15) . ? O11 C12 1.355(5) . ? O11 Cu1 1.961(3) 2 ? C12 C13 1.392(7) . ? C12 C17 1.397(7) . ? C13 C14 1.401(7) . ? C13 H13 0.9300 . ? C14 C15 1.368(8) . ? C14 H14 0.9300 . ? C15 C16 1.367(7) . ? C15 H15 0.9300 . ? C16 C17 1.394(6) . ? C16 H16 0.9300 . ? C17 C18 1.500(7) . ? C18 N19 1.496(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N19 C20 1.469(6) . ? N19 H19 0.9100 . ? C20 C21 1.505(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N22 1.473(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? N22 C24 1.481(5) . ? N22 C23 1.487(6) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? O1 H1 0.77(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 O11 Cu1 O11 75.22(13) 2 . ? O11 Cu1 N19 155.14(14) 2 . ? O11 Cu1 N19 90.75(14) . . ? O11 Cu1 N22 99.22(15) 2 . ? O11 Cu1 N22 158.86(15) . . ? N19 Cu1 N22 86.47(15) . . ? O11 Cu1 Cl2 109.01(10) 2 . ? O11 Cu1 Cl2 102.68(11) . . ? N19 Cu1 Cl2 93.88(12) . . ? N22 Cu1 Cl2 98.42(13) . . ? C12 O11 Cu1 136.1(3) . 2 ? C12 O11 Cu1 121.6(3) . . ? Cu1 O11 Cu1 102.28(13) 2 . ? O11 C12 C13 120.8(5) . . ? O11 C12 C17 119.0(4) . . ? C13 C12 C17 120.1(4) . . ? C12 C13 C14 119.2(6) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.5(5) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.2(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 121.2(5) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C16 C17 C12 118.8(5) . . ? C16 C17 C18 122.0(5) . . ? C12 C17 C18 119.2(4) . . ? N19 C18 C17 110.1(4) . . ? N19 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? N19 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C20 N19 C18 113.1(4) . . ? C20 N19 Cu1 107.8(3) . . ? C18 N19 Cu1 114.6(3) . . ? C20 N19 H19 107.0 . . ? C18 N19 H19 107.0 . . ? Cu1 N19 H19 107.0 . . ? N19 C20 C21 107.3(4) . . ? N19 C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? N19 C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? N22 C21 C20 111.7(4) . . ? N22 C21 H21A 109.3 . . ? C20 C21 H21A 109.3 . . ? N22 C21 H21B 109.3 . . ? C20 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C21 N22 C24 109.0(4) . . ? C21 N22 C23 110.5(4) . . ? C24 N22 C23 108.7(4) . . ? C21 N22 Cu1 103.3(3) . . ? C24 N22 Cu1 115.5(3) . . ? C23 N22 Cu1 109.7(3) . . ? N22 C23 H23A 109.5 . . ? N22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N22 C24 H24A 109.5 . . ? N22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.952 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.120 data_3 _database_code_depnum_ccdc_archive 'CCDC 886054' #TrackingRef '1-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H38 Cl2 Cu3 N10 O12 ' _chemical_formula_weight 896.14 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.676(3) _cell_length_b 15.090(4) _cell_length_c 13.092(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.24(3) _cell_angle_gamma 90.00 _cell_volume 1691.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9188 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 30.00 _exptl_crystal_description rectangle _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 914 _exptl_absorpt_coefficient_mu 2.099 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'ABSPACK, Oxford Diffraction Ltd' _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 9188 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.1433 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4657 _reflns_number_gt 2413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0772P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4657 _refine_ls_number_parameters 240 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1591 _refine_ls_R_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.2076 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 0.33656(9) 0.01838(4) 0.68412(6) 0.0293(2) Uani 1 1 d . . . Cu2 Cu 0.5000 0.0000 0.5000 0.0371(3) Uani 1 2 d S . . O11 O 0.3738(5) -0.0685(2) 0.5787(3) 0.0318(10) Uani 1 1 d . . . C12 C 0.2811(7) -0.1425(3) 0.5587(5) 0.0267(14) Uani 1 1 d . . . C13 C 0.2158(8) -0.1651(4) 0.4602(5) 0.0339(15) Uani 1 1 d . . . H13 H 0.2374 -0.1318 0.4044 0.041 Uiso 1 1 calc R . . C14 C 0.1151(8) -0.2394(4) 0.4434(6) 0.0385(16) Uani 1 1 d . . . H14 H 0.0711 -0.2553 0.3764 0.046 Uiso 1 1 calc R . . C15 C 0.0826(8) -0.2882(4) 0.5265(6) 0.0423(18) Uani 1 1 d . . . H15 H 0.0149 -0.3363 0.5159 0.051 Uiso 1 1 calc R . . C16 C 0.1515(8) -0.2649(4) 0.6264(6) 0.0374(17) Uani 1 1 d . . . H16 H 0.1305 -0.2985 0.6821 0.045 Uiso 1 1 calc R . . C17 C 0.2512(7) -0.1926(3) 0.6445(5) 0.0290(14) Uani 1 1 d . . . C18 C 0.3261(8) -0.1656(4) 0.7500(5) 0.0340(15) Uani 1 1 d . . . H18A H 0.4386 -0.1643 0.7535 0.041 Uiso 1 1 calc R . . H18B H 0.3013 -0.2083 0.8002 0.041 Uiso 1 1 calc R . . N19 N 0.2690(6) -0.0759(3) 0.7747(4) 0.0314(12) Uani 1 1 d . . . H19 H 0.1628 -0.0772 0.7639 0.038 Uiso 1 1 calc R . . C20 C 0.3220(8) -0.0468(4) 0.8809(5) 0.0381(16) Uani 1 1 d . . . H20A H 0.4344 -0.0532 0.8986 0.046 Uiso 1 1 calc R . . H20B H 0.2731 -0.0820 0.9288 0.046 Uiso 1 1 calc R . . C21 C 0.2752(8) 0.0505(4) 0.8864(5) 0.0385(16) Uani 1 1 d . . . H21A H 0.1623 0.0557 0.8745 0.046 Uiso 1 1 calc R . . H21B H 0.3143 0.0740 0.9546 0.046 Uiso 1 1 calc R . . N22 N 0.3417(6) 0.1018(3) 0.8063(4) 0.0293(12) Uani 1 1 d . . . C23 C 0.2471(9) 0.1845(4) 0.7819(6) 0.0433(18) Uani 1 1 d . . . H23A H 0.1432 0.1690 0.7501 0.065 Uiso 1 1 calc R . . H23B H 0.2947 0.2208 0.7354 0.065 Uiso 1 1 calc R . . H23C H 0.2430 0.2167 0.8447 0.065 Uiso 1 1 calc R . . C24 C 0.5049(8) 0.1273(4) 0.8444(5) 0.0391(17) Uani 1 1 d . . . H24A H 0.5493 0.1539 0.7892 0.059 Uiso 1 1 calc R . . H24B H 0.5640 0.0755 0.8688 0.059 Uiso 1 1 calc R . . H24C H 0.5078 0.1690 0.9001 0.059 Uiso 1 1 calc R . . N1 N 0.4526(7) 0.0945(3) 0.5980(4) 0.0377(14) Uani 1 1 d . . . N2 N 0.4219(7) 0.1702(4) 0.5703(5) 0.0448(16) Uani 1 1 d . . . N3 N 0.3960(9) 0.2429(4) 0.5462(5) 0.061(2) Uani 1 1 d . . . Cl8 Cl 0.8111(2) -0.05133(11) 0.7324(2) 0.0373(5) Uani 0.84 1 d P . . O81 O 0.9220(6) -0.1189(3) 0.7657(4) 0.0538(14) Uani 1 1 d . . . O82 O 0.8891(6) 0.0344(3) 0.7525(5) 0.0585(16) Uani 1 1 d . . . O84A O 0.7597(7) -0.0583(4) 0.6204(5) 0.0570(17) Uani 0.84 1 d P . . O83 O 0.6787(7) -0.0581(4) 0.7748(6) 0.083(2) Uani 1 1 d . . . Cl9 Cl 0.8293(12) -0.0401(6) 0.7917(8) 0.026(2) Uiso 0.16 1 d P . . O84B O 0.820(4) -0.0247(19) 0.889(3) 0.052(8) Uiso 0.16 1 d P . . O1W O 0.1046(7) 0.0524(4) 0.5853(5) 0.0644(16) Uani 1 1 d D . . H1 H 0.097(8) 0.071(6) 0.521(3) 0.077 Uiso 1 1 d D . . H2 H 0.015(5) 0.050(5) 0.603(5) 0.077 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0347(5) 0.0218(4) 0.0333(5) 0.0010(3) 0.0114(4) -0.0018(3) Cu2 0.0530(8) 0.0210(5) 0.0440(7) -0.0007(4) 0.0281(6) -0.0052(4) O11 0.037(3) 0.023(2) 0.040(3) 0.0004(17) 0.017(2) -0.0024(17) C12 0.029(4) 0.014(2) 0.038(4) 0.000(2) 0.009(3) 0.001(2) C13 0.041(4) 0.025(3) 0.035(4) 0.000(2) 0.006(3) 0.010(3) C14 0.037(4) 0.032(3) 0.045(4) -0.013(3) 0.001(3) 0.005(3) C15 0.040(4) 0.023(3) 0.069(5) -0.009(3) 0.025(4) -0.009(3) C16 0.045(5) 0.022(3) 0.050(5) 0.003(3) 0.024(4) 0.000(3) C17 0.024(4) 0.023(3) 0.041(4) 0.008(2) 0.010(3) 0.001(2) C18 0.043(4) 0.025(3) 0.035(4) 0.009(2) 0.011(3) -0.001(2) N19 0.032(3) 0.032(3) 0.032(3) 0.005(2) 0.011(3) -0.002(2) C20 0.048(5) 0.037(3) 0.028(4) 0.006(3) 0.003(3) -0.005(3) C21 0.047(5) 0.045(4) 0.026(4) -0.006(3) 0.012(3) -0.002(3) N22 0.034(3) 0.022(2) 0.032(3) -0.0038(19) 0.008(2) -0.0004(19) C23 0.053(5) 0.031(3) 0.048(5) -0.005(3) 0.015(4) 0.014(3) C24 0.039(5) 0.036(4) 0.043(4) -0.010(3) 0.009(3) -0.012(3) N1 0.065(4) 0.019(2) 0.036(3) 0.000(2) 0.031(3) -0.005(2) N2 0.067(5) 0.030(3) 0.044(4) -0.003(2) 0.027(3) 0.003(3) N3 0.102(6) 0.029(3) 0.060(5) 0.009(3) 0.034(4) 0.013(3) Cl8 0.0291(12) 0.0263(9) 0.0560(15) 0.0031(9) 0.0049(10) 0.0000(7) O81 0.044(3) 0.036(3) 0.082(4) 0.013(3) 0.011(3) 0.010(2) O82 0.060(4) 0.030(3) 0.084(5) -0.005(3) 0.005(3) -0.012(2) O84A 0.053(4) 0.058(4) 0.057(5) -0.010(3) 0.000(3) 0.004(3) O83 0.058(4) 0.060(4) 0.141(7) -0.015(4) 0.040(4) 0.000(3) O1W 0.056(4) 0.071(4) 0.062(4) -0.003(3) 0.000(3) 0.026(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 O11 1.968(4) . ? Cu1 N1 1.992(4) . ? Cu1 N19 1.999(4) . ? Cu1 N22 2.031(5) . ? Cu1 O1W 2.269(6) . ? Cu1 Cu2 2.9994(12) . ? Cu2 O11 1.921(4) . ? Cu2 O11 1.921(4) 3_656 ? Cu2 N1 2.004(5) . ? Cu2 N1 2.004(5) 3_656 ? Cu2 Cu1 2.9994(12) 3_656 ? O11 C12 1.376(6) . ? C12 C13 1.366(9) . ? C12 C17 1.412(8) . ? C13 C14 1.417(9) . ? C13 H13 0.9300 . ? C14 C15 1.380(10) . ? C14 H14 0.9300 . ? C15 C16 1.393(10) . ? C15 H15 0.9300 . ? C16 C17 1.389(8) . ? C16 H16 0.9300 . ? C17 C18 1.485(9) . ? C18 N19 1.494(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N19 C20 1.460(8) . ? N19 H19 0.9100 . ? C20 C21 1.528(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N22 1.492(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? N22 C24 1.474(8) . ? N22 C23 1.499(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N1 N2 1.216(7) . ? N2 N3 1.153(7) . ? Cl8 Cl9 0.786(10) . ? Cl8 O83 1.358(6) . ? Cl8 O81 1.422(5) . ? Cl8 O82 1.465(5) . ? Cl8 O84A 1.466(7) . ? Cl8 O84B 2.08(3) . ? O81 Cl9 1.506(10) . ? O82 Cl9 1.372(10) . ? O83 Cl9 1.318(12) . ? Cl9 O84B 1.31(3) . ? O1W H1 0.88(2) . ? O1W H2 0.84(2) . ? 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 O11 Cu1 N1 80.33(18) . . ? O11 Cu1 N19 92.20(18) . . ? N1 Cu1 N19 165.6(2) . . ? O11 Cu1 N22 168.7(2) . . ? N1 Cu1 N22 98.0(2) . . ? N19 Cu1 N22 86.9(2) . . ? O11 Cu1 O1W 88.9(2) . . ? N1 Cu1 O1W 91.7(3) . . ? N19 Cu1 O1W 100.5(2) . . ? N22 Cu1 O1W 102.4(2) . . ? O11 Cu1 Cu2 38.98(11) . . ? N1 Cu1 Cu2 41.51(13) . . ? N19 Cu1 Cu2 129.21(14) . . ? N22 Cu1 Cu2 137.48(14) . . ? O1W Cu1 Cu2 93.05(16) . . ? O11 Cu2 O11 180.0(2) . 3_656 ? O11 Cu2 N1 81.17(17) . . ? O11 Cu2 N1 98.83(17) 3_656 . ? O11 Cu2 N1 98.83(17) . 3_656 ? O11 Cu2 N1 81.17(17) 3_656 3_656 ? N1 Cu2 N1 180.000(1) . 3_656 ? O11 Cu2 Cu1 40.11(12) . . ? O11 Cu2 Cu1 139.89(12) 3_656 . ? N1 Cu2 Cu1 41.21(13) . . ? N1 Cu2 Cu1 138.79(13) 3_656 . ? O11 Cu2 Cu1 139.89(12) . 3_656 ? O11 Cu2 Cu1 40.11(12) 3_656 3_656 ? N1 Cu2 Cu1 138.79(13) . 3_656 ? N1 Cu2 Cu1 41.21(13) 3_656 3_656 ? Cu1 Cu2 Cu1 180.0 . 3_656 ? C12 O11 Cu2 134.5(4) . . ? C12 O11 Cu1 121.2(3) . . ? Cu2 O11 Cu1 100.91(17) . . ? C13 C12 O11 121.6(5) . . ? C13 C12 C17 121.1(6) . . ? O11 C12 C17 117.3(6) . . ? C12 C13 C14 119.7(6) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.9(7) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.6(6) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 121.3(6) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C12 118.3(6) . . ? C16 C17 C18 122.8(5) . . ? C12 C17 C18 118.9(5) . . ? C17 C18 N19 109.8(5) . . ? C17 C18 H18A 109.7 . . ? N19 C18 H18A 109.7 . . ? C17 C18 H18B 109.7 . . ? N19 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C20 N19 C18 114.5(5) . . ? C20 N19 Cu1 105.9(4) . . ? C18 N19 Cu1 112.2(3) . . ? C20 N19 H19 108.0 . . ? C18 N19 H19 108.0 . . ? Cu1 N19 H19 108.0 . . ? N19 C20 C21 106.8(5) . . ? N19 C20 H20A 110.4 . . ? C21 C20 H20A 110.4 . . ? N19 C20 H20B 110.4 . . ? C21 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? N22 C21 C20 109.3(5) . . ? N22 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? N22 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? C24 N22 C21 110.9(5) . . ? C24 N22 C23 108.6(5) . . ? C21 N22 C23 108.8(5) . . ? C24 N22 Cu1 109.0(3) . . ? C21 N22 Cu1 105.6(3) . . ? C23 N22 Cu1 114.0(4) . . ? N22 C23 H23A 109.5 . . ? N22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N22 C24 H24A 109.5 . . ? N22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 N1 Cu1 127.1(4) . . ? N2 N1 Cu2 122.4(4) . . ? Cu1 N1 Cu2 97.3(2) . . ? N3 N2 N1 178.1(8) . . ? Cl9 Cl8 O83 70.2(8) . . ? Cl9 Cl8 O81 80.4(8) . . ? O83 Cl8 O81 113.3(4) . . ? Cl9 Cl8 O82 67.5(7) . . ? O83 Cl8 O82 113.0(3) . . ? O81 Cl8 O82 108.0(3) . . ? Cl9 Cl8 O84A 169.9(8) . . ? O83 Cl8 O84A 105.2(4) . . ? O81 Cl8 O84A 109.7(4) . . ? O82 Cl8 O84A 107.5(4) . . ? Cl9 Cl8 O84B 9.4(12) . . ? O83 Cl8 O84B 60.8(9) . . ? O81 Cl8 O84B 85.4(9) . . ? O82 Cl8 O84B 73.0(9) . . ? O84A Cl8 O84B 163.3(9) . . ? Cl8 O81 Cl9 31.0(4) . . ? Cl9 O82 Cl8 32.0(4) . . ? Cl9 O83 Cl8 34.1(4) . . ? Cl8 Cl9 O84B 164.9(19) . . ? Cl8 Cl9 O83 75.7(9) . . ? O84B Cl9 O83 89.2(15) . . ? Cl8 Cl9 O82 80.5(8) . . ? O84B Cl9 O82 107.7(15) . . ? O83 Cl9 O82 122.1(8) . . ? Cl8 Cl9 O81 68.6(7) . . ? O84B Cl9 O81 118.6(15) . . ? O83 Cl9 O81 110.4(7) . . ? O82 Cl9 O81 108.4(7) . . ? Cl9 O84B Cl8 5.7(7) . . ? Cu1 O1W H1 123(5) . . ? Cu1 O1W H2 127(5) . . ? H1 O1W H2 110(3) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 1.028 _refine_diff_density_min -1.109 _refine_diff_density_rms 0.154