# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Ramon Vicente' 'Albert Escuer' 'Merce Font-Bardia' 'Salah S. Massoud' 'Franz A. Mautner' 'Evaristo Penalba' 'Xavier Solans' _publ_contact_author_name 'Dr Ramon Vicente' _publ_contact_author_address ; Química Inorganica Universitat de Barcelona Marti i Franques 1-11 Barcelona 08028 SPAIN ; _publ_contact_author_email RAMON.VICENTE@QI.UB.ES _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Three New Dinuclear Copper(II) Complexes with [Cu(m1,3-N3)2Cu]2+ and [Cu(m1,1-N3)2Cu]2+ Asymmetrical Cores: Syntheses, Structure and Magnetic Behavior. ; data_ssma1 _database_code_depnum_ccdc_archive 'CCDC 229685' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(Medpt)(N3)](ClO4)' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C7 H19 Cl Cu N6 O4' _chemical_formula_weight 350.27 _chemical_melting_point ? _chemical_compound_source ? 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' Cu Cu 0.3201 1.2651 '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' _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 7.536(2) _cell_length_b 12.597(3) _cell_length_c 14.629(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.77(2) _cell_angle_gamma 90.00 _cell_volume 1368.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 56 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 17.2 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 1.68(3) _exptl_crystal_density_diffrn 1.700 _exptl_crystal_density_method 'suspension method' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.811 _exptl_absorpt_correction_type DIFABS _exptl_absorpt_correction_T_min 0.556 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'mod. STOE 4-circle diffractometer' _diffrn_measurement_method 'Omega-scan; delta Omega: 1.20 deg.' _diffrn_standards_number '2 (-1 1 -1; 0 -2 3)' _diffrn_standards_interval_count 100 _diffrn_standards_interval_time '1 h' _diffrn_standards_decay_% 3 _diffrn_reflns_number 3248 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2684 _reflns_number_observed 2223 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL/PC v.5.03 (Siemens Ind. Aut.)' _computing_publication_material 'SHELXTL/PC v.5.03 (Siemens Ind. Aut.)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 22 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.6025P] 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 2662 _refine_ls_number_parameters 187 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_obs 0.0387 _refine_ls_wR_factor_all 0.1014 _refine_ls_wR_factor_obs 0.0916 _refine_ls_goodness_of_fit_all 1.080 _refine_ls_goodness_of_fit_obs 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_restrained_S_obs 1.099 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.26703(5) 0.10604(3) 0.08219(2) 0.03118(13) Uani 1 d . . N11 N 0.2274(4) 0.0501(3) -0.0545(2) 0.0453(7) Uani 1 d . . N12 N 0.3358(3) -0.0006(2) -0.0838(2) 0.0345(6) Uani 1 d . . N13 N 0.5633(4) 0.0511(3) 0.1160(2) 0.0570(9) Uani 1 d . . N1 N 0.1868(4) -0.0357(2) 0.1162(2) 0.0423(7) Uani 1 d D . HN1A H 0.0681(15) -0.0388(37) 0.1022(30) 0.079(11) Uiso 1 d D . HN1B H 0.2381(53) -0.0793(29) 0.0808(26) 0.079(11) Uiso 1 d D . C1 C 0.2381(6) -0.0725(3) 0.2120(3) 0.0582(10) Uani 1 d . . H1A H 0.3682(6) -0.0719(3) 0.2290(3) 0.070 Uiso 1 calc R . H1B H 0.1969(6) -0.1449(3) 0.2170(3) 0.070 Uiso 1 calc R . C2 C 0.1582(6) -0.0033(4) 0.2763(3) 0.0630(11) Uani 1 d . . H2A H 0.1785(6) -0.0354(4) 0.3374(3) 0.076 Uiso 1 calc R . H2B H 0.0292(6) 0.0005(4) 0.2554(3) 0.076 Uiso 1 calc R . C3 C 0.2328(6) 0.1065(3) 0.2836(2) 0.0571(10) Uani 1 d . . H3A H 0.1873(6) 0.1424(3) 0.3334(2) 0.068 Uiso 1 calc R . H3B H 0.3625(6) 0.1015(3) 0.3014(2) 0.068 Uiso 1 calc R . N2 N 0.1937(3) 0.1740(2) 0.1995(2) 0.0386(6) Uani 1 d . . C4 C 0.2787(5) 0.2779(3) 0.2271(3) 0.0559(10) Uani 1 d . . H4A H 0.2209(5) 0.3073(3) 0.2759(3) 0.067 Uiso 1 calc R . H4B H 0.4038(5) 0.2652(3) 0.2536(3) 0.067 Uiso 1 calc R . C5 C 0.2734(6) 0.3595(3) 0.1537(3) 0.0589(10) Uani 1 d . . H5A H 0.3103(6) 0.4270(3) 0.1826(3) 0.071 Uiso 1 calc R . H5B H 0.1501(6) 0.3671(3) 0.1219(3) 0.071 Uiso 1 calc R . C6 C 0.3905(5) 0.3349(3) 0.0837(3) 0.0588(10) Uani 1 d . . H6A H 0.3954(5) 0.3961(3) 0.0440(3) 0.071 Uiso 1 calc R . H6B H 0.5118(5) 0.3200(3) 0.1152(3) 0.071 Uiso 1 calc R . N3 N 0.3208(4) 0.2433(2) 0.0272(2) 0.0425(7) Uani 1 d D . HN3A H 0.4005(37) 0.2305(30) -0.0096(20) 0.052(8) Uiso 1 d D . HN3B H 0.2228(30) 0.2616(30) -0.0116(20) 0.052(8) Uiso 1 d D . C7 C -0.0049(5) 0.1887(3) 0.1733(3) 0.0548(10) Uani 1 d . . H7A H -0.0600(6) 0.1221(5) 0.1530(16) 0.066 Uiso 1 calc R . H7B H -0.0295(5) 0.2396(15) 0.1239(12) 0.066 Uiso 1 calc R . H7C H -0.0530(7) 0.2137(19) 0.2260(5) 0.066 Uiso 1 calc R . Cl2 Cl 0.22976(12) 0.67732(8) 0.07111(7) 0.0513(2) Uani 1 d . . O1 O 0.2838(6) 0.6339(3) 0.1601(3) 0.1021(13) Uani 1 d . . O2 O 0.0576(4) 0.7225(3) 0.0701(3) 0.0878(11) Uani 1 d . . O3 O 0.3512(5) 0.7607(3) 0.0601(3) 0.0906(11) Uani 1 d . . O4 O 0.2281(7) 0.6001(3) 0.0033(3) 0.115(2) Uani 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 0.0313(2) 0.0316(2) 0.0306(2) -0.0032(2) 0.00525(14) 0.0003(2) N11 0.0392(14) 0.056(2) 0.0375(15) -0.0119(14) -0.0023(12) 0.0085(14) N12 0.0302(13) 0.0423(15) 0.0280(13) -0.0031(12) -0.0037(11) -0.0056(12) N13 0.0356(15) 0.083(2) 0.049(2) -0.017(2) -0.0001(13) 0.013(2) N1 0.042(2) 0.035(2) 0.050(2) 0.0005(13) 0.0085(13) -0.0037(13) C1 0.069(3) 0.046(2) 0.058(2) 0.017(2) 0.009(2) -0.001(2) C2 0.078(3) 0.066(3) 0.047(2) 0.016(2) 0.016(2) -0.003(2) C3 0.070(3) 0.070(3) 0.030(2) -0.002(2) 0.003(2) -0.002(2) N2 0.0392(14) 0.042(2) 0.0338(14) -0.0086(12) 0.0046(11) -0.0035(12) C4 0.059(2) 0.050(2) 0.056(2) -0.019(2) 0.003(2) -0.007(2) C5 0.066(2) 0.039(2) 0.072(3) -0.014(2) 0.012(2) -0.006(2) C6 0.059(2) 0.037(2) 0.083(3) -0.005(2) 0.021(2) -0.013(2) N3 0.046(2) 0.040(2) 0.044(2) 0.0030(14) 0.0125(13) 0.0003(13) C7 0.041(2) 0.061(2) 0.064(2) -0.010(2) 0.014(2) 0.011(2) Cl2 0.0503(5) 0.0491(5) 0.0559(5) 0.0002(4) 0.0135(4) 0.0023(4) O1 0.119(3) 0.106(3) 0.074(2) 0.028(2) -0.005(2) 0.019(2) O2 0.046(2) 0.104(3) 0.110(3) -0.002(2) 0.005(2) 0.007(2) O3 0.081(2) 0.066(2) 0.142(3) -0.010(2) 0.068(2) -0.007(2) O4 0.161(4) 0.096(3) 0.100(3) -0.047(2) 0.051(3) -0.025(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 Cu1 5.302(1) 3_655 yes Cu1 N1 1.976(3) . yes Cu1 N3 1.978(3) . yes Cu1 N2 2.075(3) . yes Cu1 N11 2.093(3) . yes Cu1 N13 2.309(3) . yes N11 N12 1.174(4) . yes N12 N13 1.152(4) 3_655 yes N13 N12 1.152(4) 3_655 yes N1 C1 1.463(5) . yes N1 HN1A 0.884(10) . ? N1 HN1B 0.887(10) . ? C1 C2 1.483(6) . yes C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 C3 1.490(6) . yes C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 N2 1.483(4) . yes C3 H3A 0.97 . ? C3 H3B 0.97 . ? N2 C4 1.484(4) . yes N2 C7 1.492(4) . yes C4 C5 1.482(6) . yes C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.493(6) . yes C5 H5A 0.97 . ? C5 H5B 0.97 . ? C6 N3 1.465(5) . yes C6 H6A 0.97 . ? C6 H6B 0.97 . ? N3 HN3A 0.886(10) . ? N3 HN3B 0.882(10) . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? Cl2 O4 1.388(4) . yes Cl2 O1 1.408(4) . yes Cl2 O2 1.414(3) . yes Cl2 O3 1.420(3) . yes 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 N3 170.11(13) . . yes N1 Cu1 N2 91.62(12) . . yes N3 Cu1 N2 94.46(12) . . yes N1 Cu1 N11 86.37(13) . . yes N3 Cu1 N11 84.91(13) . . yes N2 Cu1 N11 156.08(10) . . yes N1 Cu1 N13 90.07(13) . . yes N3 Cu1 N13 95.27(13) . . yes N2 Cu1 N13 109.29(11) . . yes N11 Cu1 N13 94.56(11) . . yes N12 N11 Cu1 122.5(2) . . yes N13 N12 N11 177.0(3) 3_655 . yes N12 N13 Cu1 139.4(2) 3_655 . yes C1 N1 Cu1 119.0(2) . . yes C1 N1 HN1A 107.5(30) . . ? Cu1 N1 HN1A 108.8(31) . . ? C1 N1 HN1B 107.0(30) . . ? Cu1 N1 HN1B 103.3(30) . . ? HN1A N1 HN1B 111.1(40) . . ? N1 C1 C2 110.6(3) . . yes N1 C1 H1A 109.5(2) . . ? C2 C1 H1A 109.5(2) . . ? N1 C1 H1B 109.5(2) . . ? C2 C1 H1B 109.5(2) . . ? H1A C1 H1B 108.1 . . ? C1 C2 C3 113.7(3) . . yes C1 C2 H2A 108.8(2) . . ? C3 C2 H2A 108.8(2) . . ? C1 C2 H2B 108.8(2) . . ? C3 C2 H2B 108.8(2) . . ? H2A C2 H2B 107.7 . . ? N2 C3 C2 117.0(3) . . yes N2 C3 H3A 108.1(2) . . ? C2 C3 H3A 108.1(2) . . ? N2 C3 H3B 108.1(2) . . ? C2 C3 H3B 108.1(2) . . ? H3A C3 H3B 107.3 . . ? C3 N2 C4 105.3(3) . . yes C3 N2 C7 109.5(3) . . yes C4 N2 C7 109.2(3) . . yes C3 N2 Cu1 113.9(2) . . yes C4 N2 Cu1 115.2(2) . . yes C7 N2 Cu1 103.6(2) . . yes C5 C4 N2 117.2(3) . . yes C5 C4 H4A 108.0(2) . . ? N2 C4 H4A 108.0(2) . . ? C5 C4 H4B 108.0(2) . . ? N2 C4 H4B 108.0(2) . . ? H4A C4 H4B 107.2 . . ? C4 C5 C6 114.0(3) . . yes C4 C5 H5A 108.8(2) . . ? C6 C5 H5A 108.8(2) . . ? C4 C5 H5B 108.8(2) . . ? C6 C5 H5B 108.8(2) . . ? H5A C5 H5B 107.6 . . ? N3 C6 C5 110.7(3) . . yes N3 C6 H6A 109.5(2) . . ? C5 C6 H6A 109.5(2) . . ? N3 C6 H6B 109.5(2) . . ? C5 C6 H6B 109.5(2) . . ? H6A C6 H6B 108.1 . . ? C6 N3 Cu1 122.5(2) . . yes C6 N3 HN3A 105.7(25) . . ? Cu1 N3 HN3A 107.2(25) . . ? C6 N3 HN3B 109.7(26) . . ? Cu1 N3 HN3B 106.5(25) . . ? HN3A N3 HN3B 103.7(33) . . ? N2 C7 H7A 109.5(2) . . ? N2 C7 H7B 109.5(2) . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5(2) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 Cl2 O1 110.8(3) . . yes O4 Cl2 O2 112.2(3) . . yes O1 Cl2 O2 106.7(2) . . yes O4 Cl2 O3 111.4(2) . . yes O1 Cl2 O3 107.5(3) . . yes O2 Cl2 O3 108.0(2) . . yes _refine_diff_density_max 0.614 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.064 data_aee5 _database_code_depnum_ccdc_archive 'CCDC 229686' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H30 Cl2 Cu2 N12 O8' _chemical_formula_weight 644.44 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.524(6) _cell_length_b 8.780(4) _cell_length_c 11.320(6) _cell_angle_alpha 71.79(5) _cell_angle_beta 68.88(6) _cell_angle_gamma 63.20(5) _cell_volume 693.9(7) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method ? _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 1.779 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3662 _diffrn_reflns_av_R_equivalents 0.0043 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 29.90 _reflns_number_total 3528 _reflns_number_observed 3066 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 50 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1359P)^2^+0.0437P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0334(78) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3478 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_obs 0.0654 _refine_ls_wR_factor_all 0.1907 _refine_ls_wR_factor_obs 0.1587 _refine_ls_goodness_of_fit_all 1.076 _refine_ls_goodness_of_fit_obs 1.089 _refine_ls_restrained_S_all 1.225 _refine_ls_restrained_S_obs 1.089 _refine_ls_shift/esd_max -0.056 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu -0.00599(4) 0.16083(4) 0.37250(3) 0.0322(2) Uani 1 d . . N1 N 0.2251(4) 0.1904(4) 0.3481(3) 0.0407(6) Uani 1 d . . N2 N 0.0824(4) 0.1687(4) 0.1671(3) 0.0348(5) Uani 1 d . . N3 N -0.2613(4) 0.2355(5) 0.3573(3) 0.0458(7) Uani 1 d . . N4 N -0.0964(4) 0.1638(4) 0.5707(3) 0.0422(6) Uani 1 d . . N5 N -0.1895(4) 0.3052(4) 0.6305(3) 0.0417(6) Uani 1 d . . N6 N -0.2771(6) 0.4355(5) 0.6912(4) 0.0658(10) Uani 1 d . . C1 C 0.3426(5) 0.1738(6) 0.2073(4) 0.0493(8) Uani 1 d . . C2 C 0.2120(5) 0.2575(5) 0.1222(3) 0.0443(7) Uani 1 d . . C3 C -0.0903(5) 0.2896(5) 0.1275(3) 0.0423(7) Uani 1 d . . C4 C -0.2476(5) 0.2375(6) 0.2176(4) 0.0501(8) Uani 1 d . . C5 C 0.1778(6) -0.0200(5) 0.1149(3) 0.0471(8) Uani 1 d . . Cl Cl 0.72433(10) 0.72649(10) 0.32512(7) 0.0394(2) Uani 1 d . . O1 O 0.8532(6) 0.5644(5) 0.3801(4) 0.0858(12) Uani 1 d . . O2 O 0.6555(31) 0.8901(25) 0.4027(18) 0.106(7) Uani 0.50 d P . O3 O 0.8150(26) 0.7643(32) 0.1788(12) 0.072(3) Uani 0.50 d P . O4 O 0.5605(28) 0.7044(29) 0.3457(23) 0.130(8) Uani 0.50 d P . O2' O 0.6267(17) 0.8832(19) 0.3989(14) 0.060(3) Uani 0.50 d P . O3' O 0.8171(40) 0.7657(37) 0.2103(13) 0.104(6) Uani 0.50 d P . O4' O 0.5938(24) 0.6786(23) 0.3138(25) 0.112(7) Uani 0.50 d P . H1N H 0.3098(77) 0.1009(85) 0.3925(57) 0.074(16) Uiso 1 d . . H1NA H 0.1826(58) 0.3048(65) 0.3720(41) 0.048(11) Uiso 1 d . . H3N H -0.3163(65) 0.1719(65) 0.3879(45) 0.049(12) Uiso 1 d . . H3NA H -0.3427(57) 0.3483(60) 0.3960(42) 0.041(10) Uiso 1 d . . H1 H 0.4303(76) 0.2342(80) 0.1824(55) 0.073(15) Uiso 1 d . . H1A H 0.4347(88) 0.0247(91) 0.1924(63) 0.091(19) Uiso 1 d . . H2 H 0.2973(78) 0.2291(82) 0.0349(57) 0.076(16) Uiso 1 d . . H2A H 0.1103(72) 0.4264(76) 0.1424(54) 0.069(15) Uiso 1 d . . H3 H -0.0848(73) 0.2690(78) 0.0468(55) 0.073(16) Uiso 1 d . . H3A H -0.1359(65) 0.4134(71) 0.1481(47) 0.058(13) Uiso 1 d . . H4 H -0.2167(64) 0.1117(70) 0.2020(45) 0.055(12) Uiso 1 d . . H4A H -0.3612(78) 0.3499(84) 0.1894(55) 0.079(17) Uiso 1 d . . H5 H 0.2198(60) 0.0116(65) 0.0061(42) 0.050(11) Uiso 1 d . . H5A H 0.0766(61) -0.0588(62) 0.1490(43) 0.048(11) Uiso 1 d . . H5B H 0.2992(68) -0.0940(73) 0.1308(49) 0.058(13) Uiso 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 Cu 0.0363(3) 0.0324(3) 0.0311(3) -0.00005(14) -0.0125(2) -0.0165(2) N1 0.0432(14) 0.045(2) 0.0444(14) -0.0004(11) -0.0216(11) -0.0227(12) N2 0.0371(12) 0.0336(13) 0.0374(13) 0.0010(10) -0.0153(10) -0.0170(11) N3 0.0365(13) 0.054(2) 0.0466(15) 0.0014(13) -0.0122(11) -0.0230(13) N4 0.056(2) 0.0293(13) 0.0375(13) -0.0033(10) -0.0105(12) -0.0163(12) N5 0.0498(15) 0.0337(14) 0.0400(13) -0.0029(11) -0.0092(11) -0.0188(12) N6 0.079(2) 0.044(2) 0.067(2) -0.018(2) -0.005(2) -0.023(2) C1 0.040(2) 0.059(2) 0.053(2) -0.002(2) -0.0157(14) -0.025(2) C2 0.047(2) 0.053(2) 0.038(2) 0.0046(13) -0.0127(13) -0.030(2) C3 0.045(2) 0.044(2) 0.040(2) 0.0036(13) -0.0220(13) -0.0172(14) C4 0.047(2) 0.059(2) 0.056(2) -0.002(2) -0.025(2) -0.026(2) C5 0.062(2) 0.039(2) 0.040(2) -0.0066(13) -0.012(2) -0.020(2) Cl 0.0432(4) 0.0326(4) 0.0409(4) -0.0010(3) -0.0149(3) -0.0139(3) O1 0.081(2) 0.055(2) 0.098(3) 0.019(2) -0.045(2) -0.011(2) O2 0.210(18) 0.066(7) 0.083(8) 0.009(5) -0.086(9) -0.065(9) O3 0.102(7) 0.078(6) 0.010(5) 0.005(5) 0.003(4) -0.034(5) O4 0.060(7) 0.163(19) 0.141(12) 0.042(12) -0.036(7) -0.057(10) O2' 0.064(4) 0.047(5) 0.067(6) -0.036(4) -0.023(4) 0.002(4) O3' 0.181(13) 0.084(7) 0.029(8) 0.013(8) -0.015(8) -0.059(8) O4' 0.068(8) 0.075(6) 0.233(21) -0.050(10) -0.062(10) -0.029(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 2.012(3) . ? Cu N3 2.027(3) . ? Cu N4 2.098(3) . ? Cu N2 2.159(3) . ? N1 C1 1.559(5) . ? N1 H1N 0.95(6) . ? N1 H1NA 0.99(5) . ? N2 C2 1.487(4) . ? N2 C3 1.505(4) . ? N2 C5 1.675(5) . ? N3 C4 1.539(5) . ? N3 H3N 0.81(5) . ? N3 H3NA 1.04(5) . ? N4 N5 1.371(4) . ? N5 N6 1.301(5) . ? C1 C2 1.517(5) . ? C1 H1 1.02(6) . ? C1 H1A 1.21(7) . ? C2 H2 1.02(6) . ? C2 H2A 1.38(6) . ? C3 C4 1.525(5) . ? C3 H3 0.97(6) . ? C3 H3A 1.05(5) . ? C4 H4 1.07(5) . ? C4 H4A 1.09(6) . ? C5 H5 1.13(4) . ? C5 H5A 0.98(5) . ? C5 H5B 0.99(5) . ? Cl O3' 1.29(2) . ? Cl O4' 1.410(12) . ? Cl O4 1.42(2) . ? Cl O1 1.466(4) . ? Cl O3 1.554(13) . ? Cl O2' 1.571(11) . ? Cl O2 1.68(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 N1 Cu N3 155.74(14) . . ? N1 Cu N4 94.74(14) . . ? N3 Cu N4 92.67(14) . . ? N1 Cu N2 85.07(12) . . ? N3 Cu N2 86.64(13) . . ? N4 Cu N2 177.76(10) . . ? C1 N1 Cu 108.9(2) . . ? C1 N1 H1N 99.0(34) . . ? Cu N1 H1N 116.9(38) . . ? C1 N1 H1NA 115.6(25) . . ? Cu N1 H1NA 104.1(25) . . ? H1N N1 H1NA 112.8(44) . . ? C2 N2 C3 109.5(3) . . ? C2 N2 C5 111.1(3) . . ? C3 N2 C5 113.0(3) . . ? C2 N2 Cu 103.1(2) . . ? C3 N2 Cu 101.6(2) . . ? C5 N2 Cu 117.7(2) . . ? C4 N3 Cu 107.8(2) . . ? C4 N3 H3N 94.0(34) . . ? Cu N3 H3N 121.9(34) . . ? C4 N3 H3NA 119.2(24) . . ? Cu N3 H3NA 107.7(24) . . ? H3N N3 H3NA 106.6(41) . . ? N5 N4 Cu 127.9(2) . . ? N6 N5 N4 177.9(3) . . ? C2 C1 N1 106.9(3) . . ? C2 C1 H1 111.3(33) . . ? N1 C1 H1 109.5(33) . . ? C2 C1 H1A 109.2(32) . . ? N1 C1 H1A 113.4(31) . . ? H1 C1 H1A 106.5(44) . . ? N2 C2 C1 108.7(3) . . ? N2 C2 H2 109.9(35) . . ? C1 C2 H2 101.9(34) . . ? N2 C2 H2A 106.5(23) . . ? C1 C2 H2A 107.1(24) . . ? H2 C2 H2A 122.1(42) . . ? N2 C3 C4 109.6(3) . . ? N2 C3 H3 109.7(34) . . ? C4 C3 H3 101.0(33) . . ? N2 C3 H3A 111.5(28) . . ? C4 C3 H3A 99.3(26) . . ? H3 C3 H3A 123.9(45) . . ? C3 C4 N3 109.2(3) . . ? C3 C4 H4 105.7(25) . . ? N3 C4 H4 112.2(26) . . ? C3 C4 H4A 99.8(31) . . ? N3 C4 H4A 107.5(31) . . ? H4 C4 H4A 121.3(41) . . ? N2 C5 H5 106.6(25) . . ? N2 C5 H5A 101.1(27) . . ? H5 C5 H5A 113.7(36) . . ? N2 C5 H5B 113.4(32) . . ? H5 C5 H5B 99.1(37) . . ? H5A C5 H5B 122.4(44) . . ? O3' Cl O4' 107.3(16) . . ? O3' Cl O4 120.7(16) . . ? O4' Cl O4 17.3(17) . . ? O3' Cl O1 104.1(13) . . ? O4' Cl O1 104.7(9) . . ? O4 Cl O1 108.9(9) . . ? O3' Cl O3 10.2(20) . . ? O4' Cl O3 97.1(13) . . ? O4 Cl O3 110.8(13) . . ? O1 Cl O3 107.0(8) . . ? O3' Cl O2' 111.8(14) . . ? O4' Cl O2' 109.9(10) . . ? O4 Cl O2' 93.7(12) . . ? O1 Cl O2' 118.4(6) . . ? O3 Cl O2' 117.1(12) . . ? O3' Cl O2 107.5(15) . . ? O4' Cl O2 119.5(11) . . ? O4 Cl O2 103.2(13) . . ? O1 Cl O2 112.6(7) . . ? O3 Cl O2 114.2(12) . . ? O2' Cl O2 9.7(12) . . ? _refine_diff_density_max 2.163 _refine_diff_density_min -1.976 _refine_diff_density_rms 0.172 data_ae03 _database_code_depnum_ccdc_archive 'CCDC 229687' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H50 Cl2 Cu2 N12 O8' _chemical_formula_weight 784.70 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 23.638(2) _cell_length_b 11.011(2) _cell_length_c 13.924(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.65(2) _cell_angle_gamma 90.00 _cell_volume 3506.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method ? _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1717 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 29.43 _reflns_number_total 1652 _reflns_number_observed 1622 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 21 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0028(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1631 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_obs 0.0455 _refine_ls_wR_factor_all 0.2011 _refine_ls_wR_factor_obs 0.1186 _refine_ls_goodness_of_fit_all 0.915 _refine_ls_goodness_of_fit_obs 0.912 _refine_ls_restrained_S_all 1.551 _refine_ls_restrained_S_obs 0.912 _refine_ls_shift/esd_max -0.283 _refine_ls_shift/esd_mean 0.019 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.39691(3) 0.60803(8) 0.41415(6) 0.0462(3) Uani 1 d . . N1 N 0.4943(3) 0.5922(6) 0.3973(5) 0.069(2) Uani 1 d . . N2 N 0.5341(3) 0.5301(6) 0.4251(4) 0.0471(14) Uani 1 d . . N3 N 0.4227(3) 0.5303(5) 0.5487(4) 0.054(2) Uani 1 d . . N4 N 0.3628(3) 0.4537(6) 0.3439(4) 0.055(2) Uani 1 d . . N5 N 0.3595(2) 0.6918(5) 0.2823(4) 0.052(2) Uani 1 d . . N6 N 0.4007(3) 0.7784(5) 0.4746(5) 0.053(2) Uani 1 d . . C1 C 0.3310(4) 0.4818(9) 0.2395(6) 0.069(3) Uani 1 d . . C2 C 0.3102(4) 0.6100(11) 0.2340(6) 0.072(3) Uani 1 d . . C3 C 0.3390(4) 0.8114(10) 0.3115(7) 0.076(3) Uani 1 d . . C4 C 0.3848(4) 0.8672(7) 0.3930(7) 0.065(2) Uani 1 d . . C5 C 0.4010(4) 0.3442(9) 0.3523(7) 0.075(3) Uani 1 d . . C6 C 0.3692(5) 0.2278(8) 0.3238(7) 0.113(4) Uani 1 d . . H6 H 0.3969(5) 0.1624(8) 0.3313(7) 0.078(5) Uiso 1 calc R . H6A H 0.3470(5) 0.2323(8) 0.2559(7) 0.078(5) Uiso 1 calc R . H6B H 0.3434(5) 0.2138(8) 0.3658(7) 0.078(5) Uiso 1 calc R . C7 C 0.4027(3) 0.7070(9) 0.2205(6) 0.060(2) Uani 1 d . . C8 C 0.3785(4) 0.7611(8) 0.1179(6) 0.083(3) Uani 1 d . . H8 H 0.4093(4) 0.7671(8) 0.0843(6) 0.078(5) Uiso 1 calc R . H8A H 0.3631(4) 0.8405(8) 0.1241(6) 0.078(5) Uiso 1 calc R . H8B H 0.3480(4) 0.7099(8) 0.0803(6) 0.078(5) Uiso 1 calc R . C9 C 0.4559(4) 0.8099(9) 0.5496(7) 0.071(2) Uani 1 d . . C10 C 0.4540(4) 0.9318(8) 0.5995(8) 0.099(3) Uani 1 d . . H10 H 0.4907(4) 0.9463(8) 0.6466(8) 0.078(5) Uiso 1 calc R . H10A H 0.4232(4) 0.9314(8) 0.6331(8) 0.078(5) Uiso 1 calc R . H10B H 0.4468(4) 0.9949(8) 0.5502(8) 0.078(5) Uiso 1 calc R . Cl Cl 0.26096(8) 1.0414(2) 0.04533(14) 0.0602(6) Uani 1 d . . O1 O 0.3045(19) 1.1205(25) 0.1014(30) 0.130(11) Uani 0.50 d P . O1' O 0.3077(17) 1.0653(23) 0.1272(23) 0.106(11) Uani 0.50 d P . O2 O 0.2079(18) 1.1060(38) 0.0115(19) 0.071(7) Uani 0.50 d P . O2' O 0.2149(16) 1.1310(33) 0.0453(18) 0.066(7) Uani 0.50 d P . O3 O 0.2392(11) 0.9158(21) 0.0601(16) 0.076(6) Uani 0.50 d P . O3' O 0.2529(10) 0.9496(24) 0.1028(16) 0.091(7) Uani 0.50 d P . O4 O 0.2794(3) 1.0220(7) -0.0402(4) 0.115(2) Uani 1 d . . HN4 H 0.3347(34) 0.4483(69) 0.3741(57) 0.078(5) Uiso 1 d . . HN6 H 0.3694(33) 0.7745(66) 0.4999(54) 0.078(5) Uiso 1 d . . H1 H 0.3583(35) 0.4623(69) 0.1992(56) 0.078(5) Uiso 1 d . . H1A H 0.3064(35) 0.4207(72) 0.2265(58) 0.078(5) Uiso 1 d . . H2 H 0.2825(35) 0.6225(65) 0.2765(57) 0.078(5) Uiso 1 d . . H2A H 0.2955(35) 0.6324(74) 0.1786(61) 0.078(5) Uiso 1 d . . H3 H 0.3038(33) 0.7908(65) 0.3413(53) 0.078(5) Uiso 1 d . . H3A H 0.3314(41) 0.8467(84) 0.2690(64) 0.078(5) Uiso 1 d . . H4 H 0.4174(36) 0.8833(65) 0.3674(59) 0.078(5) Uiso 1 d . . H4A H 0.3684(32) 0.9499(70) 0.4164(53) 0.078(5) Uiso 1 d . . H5 H 0.4226(35) 0.3622(70) 0.3072(59) 0.078(5) Uiso 1 d . . H5A H 0.4207(36) 0.3408(75) 0.4160(59) 0.078(5) Uiso 1 d . . H7 H 0.4159(35) 0.6328(74) 0.2156(58) 0.078(5) Uiso 1 d . . H7A H 0.4266(36) 0.7630(68) 0.2556(60) 0.078(5) Uiso 1 d . . H9 H 0.4870(33) 0.8020(64) 0.5071(53) 0.078(5) Uiso 1 d . . H9A H 0.4590(35) 0.7596(67) 0.6089(60) 0.078(5) Uiso 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 Cu 0.0397(5) 0.0542(6) 0.0444(5) 0.0033(5) 0.0103(3) 0.0034(5) N1 0.041(3) 0.099(6) 0.071(4) 0.038(4) 0.021(3) 0.008(4) N2 0.045(3) 0.059(4) 0.038(3) 0.006(3) 0.012(3) -0.009(3) N3 0.050(4) 0.064(4) 0.050(3) 0.013(3) 0.015(3) 0.010(3) N4 0.047(3) 0.069(4) 0.048(4) 0.002(3) 0.012(3) 0.001(3) N5 0.047(3) 0.064(4) 0.048(3) 0.010(3) 0.016(3) 0.020(3) N6 0.043(3) 0.052(4) 0.067(4) 0.006(3) 0.018(3) 0.007(3) C1 0.068(6) 0.077(8) 0.057(5) -0.011(5) 0.006(4) -0.015(5) C2 0.051(4) 0.111(8) 0.050(5) 0.015(6) 0.006(4) 0.000(6) C3 0.078(6) 0.091(8) 0.064(6) 0.013(5) 0.029(6) 0.039(6) C4 0.074(6) 0.050(6) 0.080(6) -0.003(4) 0.038(5) 0.015(4) C5 0.071(6) 0.075(6) 0.074(6) -0.016(5) 0.009(5) 0.012(5) C6 0.133(9) 0.083(8) 0.109(8) -0.034(7) 0.003(7) -0.003(7) C7 0.057(5) 0.072(6) 0.057(5) 0.013(4) 0.025(4) 0.015(4) C8 0.096(6) 0.094(7) 0.067(5) 0.028(5) 0.037(5) 0.033(5) C9 0.055(5) 0.071(6) 0.079(6) -0.006(5) 0.003(5) -0.002(5) C10 0.085(7) 0.099(8) 0.107(8) -0.018(6) 0.014(6) -0.020(6) Cl 0.0427(10) 0.0884(15) 0.0492(11) 0.0028(11) 0.0115(8) -0.0017(10) O1 0.091(17) 0.142(29) 0.124(19) -0.019(18) -0.031(13) -0.006(20) O1' 0.078(11) 0.098(17) 0.101(18) -0.055(15) -0.053(13) 0.024(16) O2 0.057(9) 0.093(18) 0.059(15) 0.003(11) 0.004(11) 0.016(11) O2' 0.063(14) 0.074(15) 0.069(17) 0.009(12) 0.030(14) 0.012(10) O3 0.088(12) 0.052(10) 0.097(16) -0.013(10) 0.040(12) -0.023(8) O3' 0.082(14) 0.113(21) 0.092(16) 0.019(12) 0.049(12) 0.022(13) O4 0.100(5) 0.185(7) 0.073(4) -0.003(5) 0.046(4) -0.004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N3 2.009(5) . ? Cu N4 2.023(6) . ? Cu N5 2.045(5) . ? Cu N6 2.049(6) . ? Cu N1 2.380(6) . ? N1 N2 1.148(8) . ? N2 N3 1.195(8) 5_666 ? N3 N2 1.195(8) 5_666 ? N4 C1 1.490(10) . ? N4 C5 1.494(11) . ? N4 HN4 0.87(8) . ? N5 C2 1.492(11) . ? N5 C3 1.494(11) . ? N5 C7 1.503(9) . ? N6 C4 1.474(10) . ? N6 C9 1.492(10) . ? N6 HN6 0.90(7) . ? C1 C2 1.491(13) . ? C1 H1 0.98(8) . ? C1 H1A 0.88(8) . ? C2 H2 0.99(8) . ? C2 H2A 0.80(8) . ? C3 C4 1.488(13) . ? C3 H3 1.05(8) . ? C3 H3A 0.69(8) . ? C4 H4 0.94(8) . ? C4 H4A 1.07(8) . ? C5 C6 1.488(12) . ? C5 H5 0.92(8) . ? C5 H5A 0.89(8) . ? C6 H6 0.96 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C7 C8 1.520(10) . ? C7 H7 0.88(8) . ? C7 H7A 0.89(8) . ? C8 H8 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C9 C10 1.517(12) . ? C9 H9 1.06(7) . ? C9 H9A 0.98(8) . ? C10 H10 0.96 . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? Cl O3' 1.33(3) . ? Cl O4 1.384(6) . ? Cl O1' 1.40(3) . ? Cl O1 1.42(4) . ? Cl O2' 1.47(4) . ? Cl O2 1.41(4) . ? Cl O3 1.51(2) . ? O1 O1' 0.70(5) . ? O1' O3' 1.79(4) . ? O2 O2' 0.53(4) . ? O3 O3' 0.71(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 N3 Cu N4 94.8(2) . . ? N3 Cu N5 171.7(2) . . ? N4 Cu N5 85.2(2) . . ? N3 Cu N6 92.0(2) . . ? N4 Cu N6 159.7(2) . . ? N5 Cu N6 85.4(2) . . ? N3 Cu N1 89.3(2) . . ? N4 Cu N1 99.7(3) . . ? N5 Cu N1 98.9(2) . . ? N6 Cu N1 99.5(3) . . ? N2 N1 Cu 137.8(5) . . ? N1 N2 N3 176.2(6) . 5_666 ? N2 N3 Cu 123.8(4) 5_666 . ? C1 N4 C5 112.9(7) . . ? C1 N4 Cu 109.8(5) . . ? C5 N4 Cu 118.8(5) . . ? C1 N4 HN4 103.1(51) . . ? C5 N4 HN4 115.2(52) . . ? Cu N4 HN4 94.8(51) . . ? C2 N5 C3 112.7(7) . . ? C2 N5 C7 112.1(6) . . ? C3 N5 C7 111.8(7) . . ? C2 N5 Cu 104.1(5) . . ? C3 N5 Cu 104.5(4) . . ? C7 N5 Cu 111.2(4) . . ? C4 N6 C9 113.1(7) . . ? C4 N6 Cu 108.4(5) . . ? C9 N6 Cu 116.1(5) . . ? C4 N6 HN6 105.1(48) . . ? C9 N6 HN6 113.4(48) . . ? Cu N6 HN6 99.4(48) . . ? N4 C1 C2 109.0(7) . . ? N4 C1 H1 105.6(46) . . ? C2 C1 H1 115.8(46) . . ? N4 C1 H1A 100.8(53) . . ? C2 C1 H1A 121.5(53) . . ? H1 C1 H1A 102.2(68) . . ? C1 C2 N5 109.8(7) . . ? C1 C2 H2 111.0(44) . . ? N5 C2 H2 101.8(45) . . ? C1 C2 H2A 113.4(63) . . ? N5 C2 H2A 110.2(62) . . ? H2 C2 H2A 110.0(76) . . ? C4 C3 N5 110.4(7) . . ? C4 C3 H3 106.5(40) . . ? N5 C3 H3 105.1(41) . . ? C4 C3 H3A 113.7(84) . . ? N5 C3 H3A 107.1(80) . . ? H3 C3 H3A 113.7(90) . . ? N6 C4 C3 108.0(7) . . ? N6 C4 H4 109.9(47) . . ? C3 C4 H4 107.1(49) . . ? N6 C4 H4A 111.8(40) . . ? C3 C4 H4A 109.5(40) . . ? H4 C4 H4A 110.4(61) . . ? C6 C5 N4 114.8(8) . . ? C6 C5 H5 109.4(51) . . ? N4 C5 H5 101.5(51) . . ? C6 C5 H5A 109.3(57) . . ? N4 C5 H5A 105.3(54) . . ? H5 C5 H5A 116.6(79) . . ? C5 C6 H6 109.5(6) . . ? C5 C6 H6A 109.5(6) . . ? H6 C6 H6A 109.5 . . ? C5 C6 H6B 109.5(6) . . ? H6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N5 C7 C8 115.7(6) . . ? N5 C7 H7 104.2(52) . . ? C8 C7 H7 110.3(54) . . ? N5 C7 H7A 101.0(51) . . ? C8 C7 H7A 106.2(52) . . ? H7 C7 H7A 119.7(75) . . ? C7 C8 H8 109.5(4) . . ? C7 C8 H8A 109.5(5) . . ? H8 C8 H8A 109.5 . . ? C7 C8 H8B 109.5(5) . . ? H8 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N6 C9 C10 113.8(7) . . ? N6 C9 H9 101.4(40) . . ? C10 C9 H9 115.8(41) . . ? N6 C9 H9A 108.9(48) . . ? C10 C9 H9A 96.8(45) . . ? H9 C9 H9A 120.6(66) . . ? C9 C10 H10 109.5(5) . . ? C9 C10 H10A 109.5(5) . . ? H10 C10 H10A 109.5 . . ? C9 C10 H10B 109.5(6) . . ? H10 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3' Cl O4 121.6(10) . . ? O3' Cl O1' 81.7(17) . . ? O4 Cl O1' 112.0(18) . . ? O3' Cl O1 109.2(17) . . ? O4 Cl O1 103.0(21) . . ? O1' Cl O1 28.8(18) . . ? O3' Cl O2' 106.9(18) . . ? O4 Cl O2' 119.9(11) . . ? O1' Cl O2' 107.8(16) . . ? O1 Cl O2' 91.2(19) . . ? O3' Cl O2 109.4(21) . . ? O4 Cl O2 103.7(12) . . ? O1' Cl O2 128.9(16) . . ? O1 Cl O2 109.4(19) . . ? O2' Cl O2 21.3(15) . . ? O3' Cl O3 28.0(10) . . ? O4 Cl O3 99.7(9) . . ? O1' Cl O3 106.7(16) . . ? O1 Cl O3 135.4(14) . . ? O2' Cl O3 109.7(18) . . ? O2 Cl O3 101.7(21) . . ? O1' O1 Cl 73.7(52) . . ? O1 O1' Cl 77.5(50) . . ? O1 O1' O3' 122.8(62) . . ? Cl O1' O3' 47.6(13) . . ? O2' O2 Cl 85.1(82) . . ? O2 O2' Cl 73.6(81) . . ? O3' O3 Cl 62.1(37) . . ? O3 O3' Cl 89.9(42) . . ? O3 O3' O1' 133.8(47) . . ? Cl O3' O1' 50.7(12) . . ? _refine_diff_density_max 0.282 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.066