# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 186/1537 # CIF data for structures 1, 2, 6 and 7 only. data_(1) _audit_creation_method SHELXL-97 _chemical_formula_sum 'C20 H44 Cl2 Cu N4 O10' _chemical_formula_weight 635.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.5256(5) _cell_length_b 15.5111(9) _cell_length_c 10.8567(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.1760(10) _cell_angle_gamma 90.00 _cell_volume 1408.48(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_description columnar _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type SHELXTL-plus _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.928 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.873 _refine_diff_density_max 0.389 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.057 _diffrn_reflns_number 7673 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 27.95 _reflns_number_total 4110 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0630P)^2^+1.1864P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'heavy atom method' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_Flack 0.21(2) _refine_ls_number_reflns 4110 _refine_ls_number_parameters 340 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.077 _refine_ls_shift/su_mean 0.014 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 0.94463(13) 0.75283(4) 0.90388(11) 0.04952(16) Uani 1 1 d . . . O1 O 1.1170(6) 0.8250(3) 0.7681(5) 0.0642(12) Uani 1 1 d . . . H1O1 H 1.1844 0.8635 0.7800 0.080 Uiso 1 1 calc R . . O2 O 0.7685(7) 0.6664(3) 1.0314(5) 0.0746(14) Uani 1 1 d . . . H1O2 H 0.7144 0.6228 1.0132 0.080 Uiso 1 1 calc R . . N1 N 1.0200(7) 0.6330(3) 0.8763(6) 0.0555(13) Uani 1 1 d . . . H1N1 H 0.9761 0.6011 0.9312 0.080 Uiso 1 1 calc R . . N2 N 0.8035(10) 0.7448(3) 0.7280(7) 0.0569(16) Uani 1 1 d . . . N3 N 0.8804(6) 0.8749(3) 0.9318(5) 0.0527(13) Uani 1 1 d . . . H1N3 H 0.9275 0.9055 0.8773 0.080 Uiso 1 1 calc R . . N4 N 1.0701(9) 0.7575(3) 1.0902(7) 0.0596(17) Uani 1 1 d . . . C1 C 0.9348(10) 0.6017(4) 0.7528(8) 0.0641(18) Uani 1 1 d . . . H1A H 0.9146 0.5403 0.7576 0.080 Uiso 1 1 calc R . . H1B H 1.0008 0.6106 0.6905 0.080 Uiso 1 1 calc R . . C2 C 0.7799(9) 0.6485(4) 0.7141(8) 0.0616(18) Uani 1 1 d . . . H2A H 0.7052 0.6294 0.7655 0.080 Uiso 1 1 calc R . . H2B H 0.7344 0.6348 0.6273 0.080 Uiso 1 1 calc R . . C3 C 0.6362(8) 0.7870(4) 0.7325(7) 0.0651(15) Uani 1 1 d . . . H3 H 0.5905 0.7573 0.7970 0.080 Uiso 1 1 calc R . . C4 C 0.6479(8) 0.8811(4) 0.7636(6) 0.0663(15) Uani 1 1 d . . . H4A H 0.5427 0.9065 0.7375 0.080 Uiso 1 1 calc R . . H4B H 0.7179 0.9078 0.7142 0.080 Uiso 1 1 calc R . . C5 C 0.7082(8) 0.9036(4) 0.8995(7) 0.0590(15) Uani 1 1 d . . . C6 C 0.9666(9) 0.9055(4) 1.0572(7) 0.0599(16) Uani 1 1 d . . . H6A H 0.8968 0.9017 1.1177 0.080 Uiso 1 1 calc R . . H6B H 0.9980 0.9653 1.0516 0.080 Uiso 1 1 calc R . . C7 C 1.1119(9) 0.8507(4) 1.0990(7) 0.0613(17) Uani 1 1 d . . . H7A H 1.1897 0.8628 1.0469 0.080 Uiso 1 1 calc R . . H7B H 1.1599 0.8648 1.1851 0.080 Uiso 1 1 calc R . . C8 C 1.2125(8) 0.6993(4) 1.1227(7) 0.0676(16) Uani 1 1 d . . . H8 H 1.1745 0.6438 1.1486 0.080 Uiso 1 1 calc R . . C9 C 1.2798(7) 0.6835(4) 1.0077(7) 0.0695(16) Uani 1 1 d . . . H9A H 1.3919 0.6690 1.0342 0.080 Uiso 1 1 calc R . . H9B H 1.2748 0.7373 0.9615 0.080 Uiso 1 1 calc R . . C10 C 1.1992(9) 0.6110(4) 0.9131(8) 0.0670(19) Uani 1 1 d . . . C11 C 0.5227(14) 0.7716(6) 0.6013(12) 0.100(3) Uani 1 1 d . . . H11A H 0.5302 0.7125 0.5766 0.080 Uiso 1 1 calc R . . H11B H 0.5543 0.8086 0.5396 0.080 Uiso 1 1 calc R . . H11C H 0.4144 0.7843 0.6078 0.080 Uiso 1 1 calc R . . C12 C 0.6116(10) 0.8675(4) 0.9910(8) 0.0684(19) Uani 1 1 d . . . H12A H 0.6320 0.8069 1.0018 0.080 Uiso 1 1 calc R . . H12B H 0.4998 0.8767 0.9588 0.080 Uiso 1 1 calc R . . H12C H 0.6418 0.8961 1.0705 0.080 Uiso 1 1 calc R . . C13 C 0.6995(12) 1.0048(5) 0.9052(14) 0.123(5) Uani 1 1 d . . . H13A H 0.7719 1.0294 0.8573 0.080 Uiso 1 1 calc R . . H13B H 0.7286 1.0235 0.9909 0.080 Uiso 1 1 calc R . . H13C H 0.5925 1.0234 0.8710 0.080 Uiso 1 1 calc R . . C14 C 1.3437(14) 0.7293(7) 1.2262(11) 0.108(4) Uani 1 1 d . . . H14A H 1.4125 0.6817 1.2561 0.080 Uiso 1 1 calc R . . H14B H 1.2983 0.7519 1.2938 0.080 Uiso 1 1 calc R . . H14C H 1.4044 0.7735 1.1950 0.080 Uiso 1 1 calc R . . C15 C 1.2827(11) 0.6183(5) 0.8034(8) 0.074(2) Uani 1 1 d . . . H15A H 1.2430 0.5747 0.7426 0.080 Uiso 1 1 calc R . . H15B H 1.3956 0.6107 0.8320 0.080 Uiso 1 1 calc R . . H15C H 1.2627 0.6742 0.7658 0.080 Uiso 1 1 calc R . . C16 C 1.2138(11) 0.5224(5) 0.9639(13) 0.121(4) Uani 1 1 d . . . H16A H 1.1789 0.4821 0.8971 0.080 Uiso 1 1 calc R . . H16B H 1.1486 0.5165 1.0262 0.080 Uiso 1 1 calc R . . H16C H 1.3234 0.5110 1.0012 0.080 Uiso 1 1 calc R . . C17 C 0.8814(13) 0.7752(6) 0.6255(8) 0.087(3) Uani 1 1 d . . . H17A H 0.7987 0.7993 0.5606 0.080 Uiso 1 1 calc R . . H17B H 0.9237 0.7250 0.5898 0.080 Uiso 1 1 calc R . . C18 C 1.0115(13) 0.8393(6) 0.6535(9) 0.093(3) Uani 1 1 d . . . H18A H 1.0717 0.8386 0.5864 0.080 Uiso 1 1 calc R . . H18B H 0.9648 0.8963 0.6552 0.080 Uiso 1 1 calc R . . C19 C 0.9607(12) 0.7368(5) 1.1817(8) 0.075(2) Uani 1 1 d . . . H19A H 1.0250 0.7329 1.2656 0.080 Uiso 1 1 calc R . . H19B H 0.8862 0.7842 1.1812 0.080 Uiso 1 1 calc R . . C20 C 0.8686(11) 0.6559(4) 1.1536(8) 0.073(2) Uani 1 1 d . . . H20A H 0.9404 0.6074 1.1536 0.080 Uiso 1 1 calc R . . H20B H 0.8036 0.6455 1.2163 0.080 Uiso 1 1 calc R . . Cl1 Cl 1.2117(2) 1.04615(10) 0.85240(17) 0.0707(5) Uani 1 1 d . . . Cl2 Cl 0.6903(2) 0.44612(10) 0.94890(17) 0.0686(5) Uani 1 1 d . . . O3 O 1.2763(8) 0.9845(4) 0.7759(7) 0.0892(19) Uani 1 1 d . . . O4 O 1.0441(9) 1.0429(4) 0.8177(9) 0.111(2) Uani 1 1 d . . . O5 O 1.2698(11) 1.1282(4) 0.8323(7) 0.117(3) Uani 1 1 d . . . O6 O 1.2607(10) 1.0208(5) 0.9807(7) 0.109(2) Uani 1 1 d . . . O7 O 0.6207(9) 0.5070(4) 1.0219(7) 0.096(2) Uani 1 1 d . . . O8 O 0.6466(12) 0.4683(4) 0.8212(7) 0.119(3) Uani 1 1 d . . . O9 O 0.8582(9) 0.4512(5) 0.9895(9) 0.113(3) Uani 1 1 d . . . O10 O 0.6310(11) 0.3633(4) 0.9699(7) 0.114(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0476(3) 0.0515(3) 0.0489(3) 0.0032(2) 0.0079(2) 0.0018(2) O1 0.059(3) 0.070(2) 0.064(3) 0.007(2) 0.011(2) 0.000(2) O2 0.077(4) 0.075(3) 0.073(4) 0.002(2) 0.018(3) -0.003(2) N1 0.055(3) 0.058(2) 0.056(3) 0.004(2) 0.015(3) 0.006(2) N2 0.063(4) 0.050(3) 0.054(4) -0.001(2) 0.004(3) 0.001(2) N3 0.045(3) 0.064(3) 0.053(3) 0.011(2) 0.018(2) 0.009(2) N4 0.054(4) 0.059(3) 0.060(4) -0.001(2) -0.002(3) 0.002(2) C1 0.070(5) 0.059(3) 0.066(5) 0.005(3) 0.019(4) 0.011(3) C2 0.060(5) 0.054(3) 0.071(5) -0.007(3) 0.011(4) -0.003(3) C3 0.060(4) 0.069(3) 0.061(4) 0.002(3) 0.001(3) 0.002(3) C4 0.059(4) 0.068(3) 0.073(4) 0.011(3) 0.015(3) 0.012(3) C5 0.046(3) 0.075(3) 0.057(4) 0.005(3) 0.012(3) 0.016(3) C6 0.062(4) 0.061(3) 0.056(4) -0.012(3) 0.010(3) 0.000(3) C7 0.060(4) 0.058(3) 0.061(4) -0.004(3) -0.002(3) -0.008(3) C8 0.058(4) 0.075(3) 0.064(4) 0.004(3) -0.003(3) 0.014(3) C9 0.047(3) 0.087(4) 0.071(4) 0.007(3) 0.001(3) 0.000(3) C10 0.060(4) 0.066(3) 0.083(5) 0.010(3) 0.033(4) 0.012(3) C11 0.081(6) 0.088(5) 0.116(8) 0.003(5) -0.021(6) 0.008(5) C12 0.061(4) 0.073(4) 0.077(5) 0.003(3) 0.027(4) 0.008(3) C13 0.074(6) 0.083(5) 0.221(14) 0.062(7) 0.051(7) 0.025(4) C14 0.095(7) 0.108(6) 0.094(7) -0.007(6) -0.045(6) 0.004(6) C15 0.070(5) 0.085(4) 0.074(5) 0.016(4) 0.031(4) 0.009(4) C16 0.062(5) 0.087(5) 0.220(13) 0.077(6) 0.042(6) 0.026(4) C17 0.114(8) 0.095(5) 0.051(4) 0.002(4) 0.009(4) -0.026(5) C18 0.100(7) 0.112(6) 0.070(6) 0.023(5) 0.023(5) -0.027(5) C19 0.105(6) 0.074(4) 0.046(4) 0.009(3) 0.013(4) -0.019(4) C20 0.087(6) 0.065(4) 0.068(5) 0.009(3) 0.017(4) 0.000(3) Cl1 0.0777(13) 0.0718(9) 0.0674(12) -0.0020(8) 0.0258(10) -0.0197(8) Cl2 0.0775(13) 0.0686(8) 0.0620(11) -0.0053(7) 0.0189(9) -0.0142(8) O3 0.073(4) 0.096(4) 0.105(5) -0.011(3) 0.034(4) -0.014(3) O4 0.079(5) 0.119(5) 0.138(7) -0.001(4) 0.031(5) 0.009(4) O5 0.170(8) 0.089(4) 0.096(6) 0.005(3) 0.035(5) -0.058(4) O6 0.133(7) 0.118(5) 0.077(5) 0.015(3) 0.024(4) -0.034(4) O7 0.091(5) 0.098(4) 0.106(5) -0.031(3) 0.039(4) -0.005(3) O8 0.194(10) 0.107(4) 0.056(4) 0.005(3) 0.024(5) -0.033(5) O9 0.065(4) 0.130(5) 0.144(8) -0.017(4) 0.021(4) 0.001(3) O10 0.179(8) 0.077(3) 0.099(6) -0.007(3) 0.064(6) -0.045(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.008(5) . ? Cu1 N3 2.011(5) . ? Cu1 N2 2.054(8) . ? Cu1 N4 2.098(8) . ? O1 C18 1.405(11) . ? O1 H1O1 0.8200 . ? O2 C20 1.441(10) . ? O2 H1O2 0.8200 . ? N1 C1 1.478(10) . ? N1 C10 1.541(10) . ? N1 H1N1 0.9100 . ? N2 C17 1.479(11) . ? N2 C2 1.511(7) . ? N2 C3 1.579(10) . ? N3 C6 1.493(9) . ? N3 C5 1.509(8) . ? N3 H1N3 0.9100 . ? N4 C7 1.487(8) . ? N4 C8 1.499(9) . ? N4 C19 1.523(12) . ? C1 C2 1.494(10) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.497(9) . ? C3 C11 1.577(12) . ? C3 H3 0.9800 . ? C4 C5 1.506(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C12 1.516(10) . ? C5 C13 1.573(10) . ? C6 C7 1.498(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.492(10) . ? C8 C14 1.497(11) . ? C8 H8 0.9800 . ? C9 C10 1.587(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C16 1.476(10) . ? C10 C15 1.505(10) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.477(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.481(10) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? Cl1 O5 1.398(5) . ? Cl1 O4 1.406(8) . ? Cl1 O6 1.430(8) . ? Cl1 O3 1.443(6) . ? Cl2 O8 1.407(8) . ? Cl2 O10 1.416(5) . ? Cl2 O9 1.415(8) . ? Cl2 O7 1.434(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 N1 Cu1 N3 177.1(3) . . ? N1 Cu1 N2 87.2(2) . . ? N3 Cu1 N2 94.0(2) . . ? N1 Cu1 N4 93.3(2) . . ? N3 Cu1 N4 85.7(2) . . ? N2 Cu1 N4 174.7(4) . . ? C18 O1 H1O1 109.5 . . ? C20 O2 H1O2 109.5 . . ? C1 N1 C10 116.8(6) . . ? C1 N1 Cu1 108.9(4) . . ? C10 N1 Cu1 119.8(4) . . ? C1 N1 H1N1 102.9 . . ? C10 N1 H1N1 102.9 . . ? Cu1 N1 H1N1 102.9 . . ? C17 N2 C2 108.1(7) . . ? C17 N2 C3 115.5(6) . . ? C2 N2 C3 108.0(6) . . ? C17 N2 Cu1 114.4(6) . . ? C2 N2 Cu1 101.3(5) . . ? C3 N2 Cu1 108.4(5) . . ? C6 N3 C5 113.8(5) . . ? C6 N3 Cu1 109.7(4) . . ? C5 N3 Cu1 121.6(4) . . ? C6 N3 H1N3 103.1 . . ? C5 N3 H1N3 103.1 . . ? Cu1 N3 H1N3 103.1 . . ? C7 N4 C8 113.4(6) . . ? C7 N4 C19 109.4(6) . . ? C8 N4 C19 106.8(6) . . ? C7 N4 Cu1 99.6(5) . . ? C8 N4 Cu1 116.4(5) . . ? C19 N4 Cu1 111.1(6) . . ? N1 C1 C2 110.4(5) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C1 C2 N2 111.0(6) . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? N2 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 N2 113.0(5) . . ? C4 C3 C11 110.7(6) . . ? N2 C3 C11 108.0(7) . . ? C4 C3 H3 108.3 . . ? N2 C3 H3 108.3 . . ? C11 C3 H3 108.3 . . ? C3 C4 C5 116.3(5) . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4B 108.2 . . ? C5 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C4 C5 N3 107.0(5) . . ? C4 C5 C12 115.5(6) . . ? N3 C5 C12 111.5(6) . . ? C4 C5 C13 105.1(7) . . ? N3 C5 C13 109.7(6) . . ? C12 C5 C13 107.9(6) . . ? N3 C6 C7 109.1(5) . . ? N3 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? N3 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? N4 C7 C6 111.0(6) . . ? N4 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? N4 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C14 109.1(8) . . ? C9 C8 N4 109.0(6) . . ? C14 C8 N4 116.3(7) . . ? C9 C8 H8 107.4 . . ? C14 C8 H8 107.4 . . ? N4 C8 H8 107.4 . . ? C8 C9 C10 118.0(6) . . ? C8 C9 H9A 107.8 . . ? C10 C9 H9A 107.8 . . ? C8 C9 H9B 107.8 . . ? C10 C9 H9B 107.8 . . ? H9A C9 H9B 107.1 . . ? C16 C10 C15 110.3(7) . . ? C16 C10 N1 108.1(6) . . ? C15 C10 N1 112.0(7) . . ? C16 C10 C9 115.1(8) . . ? C15 C10 C9 104.3(6) . . ? N1 C10 C9 107.0(5) . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 C13 H13A 109.5 . . ? C5 C13 H13B 109.4 . . ? H13A C13 H13B 109.5 . . ? C5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.4 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 119.3(8) . . ? N2 C17 H17A 107.5 . . ? C18 C17 H17A 107.5 . . ? N2 C17 H17B 107.5 . . ? C18 C17 H17B 107.5 . . ? H17A C17 H17B 107.0 . . ? O1 C18 C17 113.7(7) . . ? O1 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? O1 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 N4 114.3(7) . . ? C20 C19 H19A 108.7 . . ? N4 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? N4 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? O2 C20 C19 106.8(6) . . ? O2 C20 H20A 110.4 . . ? C19 C20 H20A 110.4 . . ? O2 C20 H20B 110.4 . . ? C19 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? O5 Cl1 O4 111.3(5) . . ? O5 Cl1 O6 110.9(5) . . ? O4 Cl1 O6 109.9(5) . . ? O5 Cl1 O3 109.1(4) . . ? O4 Cl1 O3 107.6(5) . . ? O6 Cl1 O3 107.8(5) . . ? O8 Cl2 O10 110.3(5) . . ? O8 Cl2 O9 110.6(6) . . ? O10 Cl2 O9 111.8(5) . . ? O8 Cl2 O7 108.9(5) . . ? O10 Cl2 O7 108.0(4) . . ? O9 Cl2 O7 107.0(5) . . ? data_[CuL3](ClO4)2 _audit_creation_method SHELXL-97 _chemical_formula_sum 'C22 H42 Cl2 Cu N6 O8' _chemical_formula_weight 653.06 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 orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x, y+1/2, z+1/2' '-x, -y+1, z+1' 'x+1/4, -y+5/4, z+5/4' '-x+1/4, y+5/4, z+5/4' 'x+1/2, y, z+1/2' '-x+1/2, -y+1/2, z+1' 'x+3/4, -y+3/4, z+5/4' '-x+3/4, y+3/4, z+5/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' 'x+3/4, -y+5/4, z+3/4' '-x+3/4, y+5/4, z+3/4' _cell_length_a 22.1089(9) _cell_length_b 30.5304(12) _cell_length_c 8.7632(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5915.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_description columnar _exptl_crystal_colour violet _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2744 _exptl_absorpt_coefficient_mu 0.973 _exptl_absorpt_correction_type SHELXTL-plus _exptl_absorpt_correction_T_min 0.780 _exptl_absorpt_correction_T_max 0.945 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD ' _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.377 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.062 _diffrn_reflns_number 8324 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.98 _reflns_number_total 3060 _reflns_number_gt 2761 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0652P)^2^+21.1992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'heavy atom method' _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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_number_reflns 3060 _refine_ls_number_parameters 180 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.2500 0.2500 0.99997(7) 0.03735(18) Uani 1 2 d S . . Cl1 Cl 0.23079(6) 0.38400(5) 0.68398(17) 0.0675(4) Uani 1 1 d . . . O1 O 0.2756(4) 0.3563(3) 0.7339(8) 0.167(3) Uani 1 1 d . . . O2 O 0.2536(3) 0.4127(2) 0.5729(7) 0.134(3) Uani 1 1 d . . . O3 O 0.1845(4) 0.3607(3) 0.6182(10) 0.187(4) Uani 1 1 d . . . O4 O 0.2091(5) 0.4043(2) 0.8129(10) 0.189(4) Uani 1 1 d . . . N1 N 0.24917(15) 0.31368(11) 1.0403(4) 0.0412(8) Uani 1 1 d . . . H1N1 H 0.2553 0.3271 0.9489 0.080 Uiso 1 1 calc R . . N2 N 0.15840(16) 0.25555(10) 0.9500(4) 0.0404(8) Uani 1 1 d . . . N3 N 0.1146(3) 0.2721(2) 0.4198(6) 0.0910(18) Uani 1 1 d . . . C1 C 0.1858(2) 0.32334(15) 1.0850(6) 0.0545(11) Uani 1 1 d . . . H1A H 0.1794 0.3547 1.0897 0.080 Uiso 1 1 calc R . . H1B H 0.1772 0.3110 1.1847 0.080 Uiso 1 1 calc R . . C2 C 0.14506(19) 0.30334(13) 0.9673(6) 0.0500(11) Uani 1 1 d . . . H2A H 0.1032 0.3072 0.9976 0.080 Uiso 1 1 calc R . . H2B H 0.1509 0.3180 0.8703 0.080 Uiso 1 1 calc R . . C3 C 0.1209(2) 0.22879(14) 1.0615(5) 0.0453(9) Uani 1 1 d . . . H3 H 0.1271 0.2418 1.1625 0.080 Uiso 1 1 calc R . . C4 C 0.1410(2) 0.18111(14) 1.0730(6) 0.0507(11) Uani 1 1 d . . . H4A H 0.1415 0.1693 0.9703 0.080 Uiso 1 1 calc R . . H4B H 0.1099 0.1654 1.1287 0.080 Uiso 1 1 calc R . . C5 C 0.2017(2) 0.16978(14) 1.1468(6) 0.0507(10) Uani 1 1 d . . . C6 C 0.1544(2) 0.24283(17) 0.7863(5) 0.0559(11) Uani 1 1 d . . . H6A H 0.1608 0.2115 0.7793 0.080 Uiso 1 1 calc R . . H6B H 0.1873 0.2569 0.7323 0.080 Uiso 1 1 calc R . . C7 C 0.0957(3) 0.2537(2) 0.7029(6) 0.0700(15) Uani 1 1 d . . . H7A H 0.0683 0.2289 0.7091 0.080 Uiso 1 1 calc R . . H7B H 0.0764 0.2786 0.7512 0.080 Uiso 1 1 calc R . . C8 C 0.1084(3) 0.2640(2) 0.5400(7) 0.0727(16) Uani 1 1 d . . . C9 C 0.0527(2) 0.2299(2) 1.0306(8) 0.0687(15) Uani 1 1 d . . . H9A H 0.0313 0.2218 1.1216 0.080 Uiso 1 1 calc R . . H9B H 0.0431 0.2096 0.9504 0.080 Uiso 1 1 calc R . . H9C H 0.0410 0.2589 1.0004 0.080 Uiso 1 1 calc R . . C10 C 0.2070(3) 0.12009(17) 1.1627(8) 0.0725(16) Uani 1 1 d . . . H10A H 0.1728 0.1091 1.2184 0.080 Uiso 1 1 calc R . . H10B H 0.2435 0.1130 1.2166 0.080 Uiso 1 1 calc R . . H10C H 0.2079 0.1070 1.0632 0.080 Uiso 1 1 calc R . . C11 C 0.2085(3) 0.19124(17) 1.3029(6) 0.0635(13) Uani 1 1 d . . . H11A H 0.2119 0.2224 1.2907 0.080 Uiso 1 1 calc R . . H11B H 0.2442 0.1802 1.3521 0.080 Uiso 1 1 calc R . . H11C H 0.1737 0.1846 1.3643 0.080 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 0.0392(3) 0.0322(3) 0.0407(3) 0.000 0.000 0.0011(3) Cl1 0.0716(8) 0.0624(8) 0.0686(8) 0.0187(6) -0.0154(7) -0.0109(6) O1 0.169(6) 0.206(7) 0.125(5) 0.094(5) 0.042(5) 0.106(6) O2 0.129(5) 0.142(5) 0.131(5) 0.086(4) -0.034(4) -0.059(4) O3 0.179(7) 0.207(8) 0.174(7) 0.023(6) -0.053(6) -0.128(6) O4 0.314(12) 0.124(5) 0.129(6) -0.006(5) 0.062(7) 0.055(7) N1 0.0414(16) 0.0365(16) 0.046(2) -0.0043(13) -0.0007(16) 0.0028(14) N2 0.0406(17) 0.0354(17) 0.0451(19) 0.0042(14) 0.0010(13) -0.0004(13) N3 0.128(5) 0.097(4) 0.048(3) 0.002(3) 0.003(3) 0.047(4) C1 0.055(3) 0.042(2) 0.067(3) -0.011(2) 0.008(2) 0.006(2) C2 0.043(2) 0.040(2) 0.067(3) 0.011(2) 0.000(2) 0.0058(17) C3 0.047(2) 0.048(2) 0.042(2) 0.0082(19) 0.0078(18) -0.0017(18) C4 0.050(2) 0.043(2) 0.060(3) 0.007(2) 0.003(2) -0.0104(19) C5 0.055(2) 0.039(2) 0.057(3) 0.0086(19) 0.011(2) 0.0020(18) C6 0.057(3) 0.069(3) 0.042(2) 0.001(2) 0.001(2) 0.012(2) C7 0.058(3) 0.095(4) 0.057(3) 0.000(3) -0.010(2) 0.006(3) C8 0.097(4) 0.072(3) 0.049(3) -0.007(2) -0.013(3) 0.020(3) C9 0.045(2) 0.082(4) 0.079(4) 0.025(3) 0.009(3) -0.003(2) C10 0.081(4) 0.044(3) 0.092(4) 0.012(3) 0.019(3) 0.001(2) C11 0.070(3) 0.065(3) 0.055(3) 0.005(2) 0.003(2) 0.010(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 N1 1.976(3) . ? Cu1 N1 1.976(3) 10_554 ? Cu1 N2 2.079(3) . ? Cu1 N2 2.079(3) 10_554 ? Cl1 O3 1.373(6) . ? Cl1 O4 1.374(7) . ? Cl1 O1 1.374(6) . ? Cl1 O2 1.404(5) . ? N1 C1 1.485(5) . ? N1 C5 1.518(5) 10_554 ? N1 H1N1 0.9100 . ? N2 C6 1.489(6) . ? N2 C2 1.496(5) . ? N2 C3 1.519(5) . ? N3 C8 1.090(8) . ? C1 C2 1.498(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.525(6) . ? C3 C9 1.533(6) . ? C3 H3 0.9800 . ? C4 C5 1.529(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.518(5) 10_554 ? C5 C11 1.525(7) . ? C5 C10 1.528(7) . ? C6 C7 1.525(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.489(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 N1 Cu1 N1 159.38(19) . 10_554 ? N1 Cu1 N2 87.05(13) . . ? N1 Cu1 N2 97.29(13) 10_554 . ? N1 Cu1 N2 97.29(13) . 10_554 ? N1 Cu1 N2 87.05(13) 10_554 10_554 ? N2 Cu1 N2 155.7(2) . 10_554 ? O3 Cl1 O4 108.6(7) . . ? O3 Cl1 O1 110.6(6) . . ? O4 Cl1 O1 105.5(5) . . ? O3 Cl1 O2 107.5(5) . . ? O4 Cl1 O2 114.4(5) . . ? O1 Cl1 O2 110.3(4) . . ? C1 N1 C5 116.6(3) . 10_554 ? C1 N1 Cu1 104.5(3) . . ? C5 N1 Cu1 115.5(2) 10_554 . ? C1 N1 H1N1 106.5 . . ? C5 N1 H1N1 106.5 10_554 . ? Cu1 N1 H1N1 106.5 . . ? C6 N2 C2 109.9(3) . . ? C6 N2 C3 116.5(4) . . ? C2 N2 C3 110.6(3) . . ? C6 N2 Cu1 103.9(3) . . ? C2 N2 Cu1 104.5(2) . . ? C3 N2 Cu1 110.6(2) . . ? N1 C1 C2 107.7(4) . . ? N1 C1 H1A 110.2 . . ? C2 C1 H1A 110.2 . . ? N1 C1 H1B 110.2 . . ? C2 C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? N2 C2 C1 110.4(3) . . ? N2 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? N2 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N2 C3 C4 113.4(3) . . ? N2 C3 C9 114.3(4) . . ? C4 C3 C9 108.6(4) . . ? N2 C3 H3 106.7 . . ? C4 C3 H3 106.7 . . ? C9 C3 H3 106.7 . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4A 107.3 . . ? C5 C4 H4A 107.3 . . ? C3 C4 H4B 107.3 . . ? C5 C4 H4B 107.3 . . ? H4A C4 H4B 106.9 . . ? N1 C5 C11 109.7(4) 10_554 . ? N1 C5 C10 109.4(4) 10_554 . ? C11 C5 C10 109.7(5) . . ? N1 C5 C4 107.0(4) 10_554 . ? C11 C5 C4 111.7(4) . . ? C10 C5 C4 109.3(4) . . ? N2 C6 C7 117.1(4) . . ? N2 C6 H6A 108.0 . . ? C7 C6 H6A 108.0 . . ? N2 C6 H6B 108.0 . . ? C7 C6 H6B 108.0 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C6 110.1(5) . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? N3 C8 C7 176.2(8) . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? data_6 _audit_creation_method SHELXL-97 _chemical_formula_sum 'C20 H38 Cl2 Cu N6 O8' _chemical_formula_weight 625.00 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 P21/n 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 9.25390(10) _cell_length_b 12.71980(10) _cell_length_c 11.8658(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.1870(10) _cell_angle_gamma 90.00 _cell_volume 1359.87(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_description blue _exptl_crystal_colour columnar _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.526 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 654 _exptl_absorpt_coefficient_mu 1.054 _exptl_absorpt_correction_type SHELXTL-Plus _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_T_max 0.939 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 27.68 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.250 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.047 _diffrn_reflns_number 7438 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.68 _reflns_number_total 2906 _reflns_number_gt 2458 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0414P)^2^+0.5263P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'heavy atom method' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2906 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.078 _refine_ls_shift/su_mean 0.004 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 0.0000 0.0000 0.0000 0.03457(12) Uani 1 2 d S . . N1 N 0.11983(17) 0.13011(12) 0.05770(14) 0.0355(4) Uani 1 1 d . . . N2 N 0.01988(17) 0.04469(13) -0.17145(13) 0.0338(3) Uani 1 1 d . . . N3 N 0.4141(2) -0.09308(18) -0.3454(2) 0.0646(6) Uani 1 1 d . . . C1 C 0.1833(2) 0.16440(16) -0.04141(17) 0.0405(5) Uani 1 1 d . . . H1A H 0.2666 0.1199 -0.0466 0.060 Uiso 1 1 calc R . . H1B H 0.2185 0.2363 -0.0295 0.060 Uiso 1 1 calc R . . C2 C 0.0649(2) 0.15686(15) -0.15149(17) 0.0400(4) Uani 1 1 d . . . H2A H -0.0201 0.1992 -0.1453 0.060 Uiso 1 1 calc R . . H2B H 0.1027 0.1830 -0.2160 0.060 Uiso 1 1 calc R . . C3 C -0.1265(2) 0.03868(17) -0.25978(17) 0.0383(4) Uani 1 1 d . . . H3 H -0.1936 0.0886 -0.2348 0.060 Uiso 1 1 calc R . . C4 C -0.2000(2) -0.06852(17) -0.26534(17) 0.0429(5) Uani 1 1 d . . . H4A H -0.2874 -0.0679 -0.3286 0.060 Uiso 1 1 calc R . . H4B H -0.1321 -0.1203 -0.2839 0.060 Uiso 1 1 calc R . . C5 C -0.2462(2) -0.10404(17) -0.15675(17) 0.0412(5) Uani 1 1 d . . . H5A H -0.3050 -0.0488 -0.1327 0.060 Uiso 1 1 calc R . . H5B H -0.3091 -0.1656 -0.1752 0.060 Uiso 1 1 calc R . . C6 C 0.0332(2) 0.22000(17) 0.0900(2) 0.0458(5) Uani 1 1 d . . . H6A H -0.0165 0.1977 0.1486 0.060 Uiso 1 1 calc R . . H6B H -0.0388 0.2431 0.0230 0.060 Uiso 1 1 calc R . . H6C H 0.0995 0.2769 0.1192 0.060 Uiso 1 1 calc R . . C7 C 0.1401(2) -0.01987(15) -0.20457(19) 0.0399(5) Uani 1 1 d . . . H7A H 0.0938 -0.0786 -0.2512 0.060 Uiso 1 1 calc R . . H7B H 0.2025 -0.0486 -0.1344 0.060 Uiso 1 1 calc R . . C8 C 0.2405(2) 0.03792(19) -0.2718(2) 0.0482(5) Uani 1 1 d . . . H8A H 0.1795 0.0742 -0.3377 0.060 Uiso 1 1 calc R . . H8B H 0.2999 0.0900 -0.2220 0.060 Uiso 1 1 calc R . . C9 C 0.3384(2) -0.0370(2) -0.3120(2) 0.0481(5) Uani 1 1 d . . . C10 C -0.1161(3) 0.0720(2) -0.38137(18) 0.0513(5) Uani 1 1 d . . . H10A H -0.0679 0.1392 -0.3778 0.060 Uiso 1 1 calc R . . H10B H -0.2140 0.0770 -0.4302 0.060 Uiso 1 1 calc R . . H10C H -0.0597 0.0208 -0.4126 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.10487(7) 0.30252(6) 0.46511(5) 0.05877(18) Uani 1 1 d . . . O1 O 0.0046(12) 0.2895(10) 0.3668(10) 0.109(4) Uani 0.50 1 d P . . O11 O -0.0225(11) 0.2515(9) 0.3826(11) 0.083(3) Uani 0.50 1 d P . . O2 O 0.2309(11) 0.3669(6) 0.4493(6) 0.0737(19) Uani 0.50 1 d P . . O21 O 0.2137(11) 0.3300(8) 0.4076(8) 0.104(3) Uani 0.50 1 d P . . O3 O 0.0417(6) 0.4051(5) 0.4946(7) 0.1044(19) Uani 0.50 1 d P . . O31 O 0.0552(5) 0.3404(5) 0.5595(4) 0.0817(15) Uani 0.50 1 d P . . O4 O 0.1494(7) 0.2465(7) 0.5604(6) 0.121(3) Uani 0.50 1 d P . . O41 O 0.1793(7) 0.1978(4) 0.5025(5) 0.0778(14) Uani 0.50 1 d P . . 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 0.03503(19) 0.03654(19) 0.03163(19) -0.00060(13) 0.00652(13) -0.00863(13) N1 0.0308(8) 0.0381(8) 0.0377(9) -0.0017(7) 0.0081(7) -0.0047(6) N2 0.0324(8) 0.0363(8) 0.0324(8) 0.0012(7) 0.0064(6) -0.0004(7) N3 0.0516(12) 0.0716(15) 0.0735(15) -0.0114(11) 0.0204(11) 0.0057(11) C1 0.0400(11) 0.0404(11) 0.0438(11) -0.0021(8) 0.0150(9) -0.0108(8) C2 0.0453(11) 0.0367(10) 0.0397(11) 0.0026(8) 0.0135(9) -0.0027(8) C3 0.0331(10) 0.0457(11) 0.0351(10) 0.0004(8) 0.0059(8) 0.0054(8) C4 0.0363(10) 0.0537(12) 0.0365(10) -0.0061(9) 0.0037(8) -0.0023(9) C5 0.0326(10) 0.0479(12) 0.0413(11) -0.0044(9) 0.0045(8) -0.0070(8) C6 0.0440(12) 0.0420(11) 0.0534(13) -0.0023(9) 0.0150(10) -0.0006(9) C7 0.0342(10) 0.0403(11) 0.0463(11) 0.0041(8) 0.0117(8) 0.0020(8) C8 0.0430(12) 0.0501(12) 0.0559(13) 0.0022(10) 0.0206(10) 0.0034(10) C9 0.0379(11) 0.0586(13) 0.0484(12) -0.0024(10) 0.0109(10) -0.0013(10) C10 0.0497(13) 0.0647(15) 0.0378(11) 0.0076(10) 0.0063(9) 0.0070(11) Cl1 0.0483(3) 0.0791(4) 0.0532(3) -0.0053(3) 0.0204(3) 0.0005(3) O1 0.087(7) 0.149(10) 0.072(5) -0.041(5) -0.024(4) 0.035(6) O11 0.051(3) 0.108(6) 0.093(5) -0.052(5) 0.020(3) -0.004(3) O2 0.094(4) 0.068(3) 0.071(4) 0.019(3) 0.044(4) 0.009(3) O21 0.075(4) 0.146(8) 0.107(7) 0.042(5) 0.055(5) 0.001(5) O3 0.059(3) 0.088(4) 0.165(6) -0.043(4) 0.024(3) -0.005(3) O31 0.063(3) 0.117(4) 0.074(3) -0.049(3) 0.036(2) -0.014(3) O4 0.111(5) 0.152(7) 0.092(4) 0.073(4) 0.005(4) -0.043(5) O41 0.096(4) 0.060(3) 0.072(3) 0.006(2) 0.009(3) 0.000(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 N1 2.0226(15) . ? Cu1 N1 2.0226(15) 3 ? Cu1 N2 2.1602(15) 3 ? Cu1 N2 2.1602(15) . ? N1 C5 1.494(2) 3 ? N1 C1 1.494(2) . ? N1 C6 1.496(3) . ? N2 C2 1.490(3) . ? N2 C7 1.505(2) . ? N2 C3 1.514(2) . ? N3 C9 1.133(3) . ? C1 C2 1.504(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.519(3) . ? C3 C10 1.528(3) . ? C3 H3 0.9800 . ? C4 C5 1.516(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.494(2) 3 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.542(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.468(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? Cl1 O4 1.320(5) . ? Cl1 O1 1.325(11) . ? Cl1 O21 1.384(8) . ? Cl1 O31 1.390(4) . ? Cl1 O2 1.471(9) . ? Cl1 O11 1.498(11) . ? Cl1 O3 1.503(5) . ? Cl1 O41 1.519(5) . ? O1 O11 0.59(2) . ? O2 O21 0.674(11) . ? O3 O31 1.115(7) . ? O31 O4 1.477(10) . ? O4 O41 1.009(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N1 180.0 . 3 ? N1 Cu1 N2 93.12(6) . 3 ? N1 Cu1 N2 86.88(6) 3 3 ? N1 Cu1 N2 86.88(6) . . ? N1 Cu1 N2 93.12(6) 3 . ? N2 Cu1 N2 180.0 3 . ? C5 N1 C1 107.84(15) 3 . ? C5 N1 C6 109.69(15) 3 . ? C1 N1 C6 107.96(16) . . ? C5 N1 Cu1 110.79(12) 3 . ? C1 N1 Cu1 104.83(11) . . ? C6 N1 Cu1 115.34(12) . . ? C2 N2 C7 111.54(15) . . ? C2 N2 C3 109.39(15) . . ? C7 N2 C3 112.94(15) . . ? C2 N2 Cu1 100.55(11) . . ? C7 N2 Cu1 109.22(11) . . ? C3 N2 Cu1 112.56(11) . . ? N1 C1 C2 109.01(15) . . ? N1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? N1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? N2 C2 C1 108.72(16) . . ? N2 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? N2 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N2 C3 C4 113.37(16) . . ? N2 C3 C10 113.60(17) . . ? C4 C3 C10 109.41(17) . . ? N2 C3 H3 106.7 . . ? C4 C3 H3 106.7 . . ? C10 C3 H3 106.7 . . ? C5 C4 C3 116.17(17) . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4B 108.2 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? N1 C5 C4 114.39(16) 3 . ? N1 C5 H5A 108.7 3 . ? C4 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 3 . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 116.32(16) . . ? N2 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? N2 C7 H7B 108.2 . . ? C8 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C9 C8 C7 110.39(19) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N3 C9 C8 178.2(3) . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 Cl1 O1 134.9(6) . . ? O4 Cl1 O21 116.0(5) . . ? O1 Cl1 O21 92.3(7) . . ? O4 Cl1 O31 66.0(5) . . ? O1 Cl1 O31 117.3(6) . . ? O21 Cl1 O31 136.1(4) . . ? O4 Cl1 O2 107.9(4) . . ? O1 Cl1 O2 112.0(6) . . ? O21 Cl1 O2 27.1(4) . . ? O31 Cl1 O2 109.1(3) . . ? O4 Cl1 O11 111.8(6) . . ? O1 Cl1 O11 23.3(9) . . ? O21 Cl1 O11 109.9(6) . . ? O31 Cl1 O11 108.7(4) . . ? O2 Cl1 O11 133.3(5) . . ? O4 Cl1 O3 109.3(5) . . ? O1 Cl1 O3 94.7(6) . . ? O21 Cl1 O3 105.1(5) . . ? O31 Cl1 O3 45.1(3) . . ? O2 Cl1 O3 84.8(4) . . ? O11 Cl1 O3 103.8(5) . . ? O4 Cl1 O41 40.9(4) . . ? O1 Cl1 O41 109.1(6) . . ? O21 Cl1 O41 91.9(5) . . ? O31 Cl1 O41 106.2(4) . . ? O2 Cl1 O41 101.9(4) . . ? O11 Cl1 O41 92.8(5) . . ? O3 Cl1 O41 150.2(4) . . ? O11 O1 Cl1 95(2) . . ? O1 O11 Cl1 61.8(19) . . ? O21 O2 Cl1 69.3(14) . . ? O2 O21 Cl1 83.6(14) . . ? O31 O3 Cl1 62.1(3) . . ? O3 O31 Cl1 72.8(4) . . ? O3 O31 O4 125.1(5) . . ? Cl1 O31 O4 54.7(3) . . ? O41 O4 Cl1 80.1(5) . . ? O41 O4 O31 138.1(7) . . ? Cl1 O4 O31 59.3(3) . . ? O4 O41 Cl1 58.9(4) . . ? data_7 _audit_creation_method SHELXL-97 _chemical_formula_sum 'C18 H40 Cl2 Cu N4 O14' _chemical_formula_weight 670.98 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 8.8330(18) _cell_length_b 9.8814(12) _cell_length_c 16.1678(16) _cell_angle_alpha 90.00 _cell_angle_beta 81.694(17) _cell_angle_gamma 90.00 _cell_volume 1396.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_description equant _exptl_crystal_colour blue _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 702 _exptl_absorpt_coefficient_mu 1.046 _exptl_absorpt_correction_type PNRCVAX _exptl_absorpt_correction_T_min 0.685 _exptl_absorpt_correction_T_max 0.999 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonious CAD4' _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.850 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.087 _diffrn_reflns_number 2442 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 24.96 _reflns_number_total 2442 _reflns_number_gt 1798 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0787P)^2^+2.5041P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'heavy atom method' _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 2442 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1545 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.0000 0.0000 0.0000 0.0301(2) Uani 1 2 d S . . N1 N 0.1481(4) 0.0111(3) -0.1115(2) 0.0443(9) Uani 1 1 d . . . N2 N -0.1055(4) 0.1756(3) -0.0392(2) 0.0407(8) Uani 1 1 d . . . O1 O 0.1399(4) 0.3908(3) 0.0667(2) 0.0632(10) Uani 1 1 d . . . H1O1 H 0.2400 0.3732 0.0997 0.080 Uiso 1 1 d . . . O2 O 0.1449(4) 0.1684(3) 0.0506(2) 0.0492(8) Uani 1 1 d . . . C1 C 0.1237(7) 0.1483(5) -0.1437(3) 0.0640(14) Uani 1 1 d . . . H1A H 0.1640 0.1527 -0.2027 0.080 Uiso 1 1 calc R . . H1B H 0.1780 0.2141 -0.1145 0.080 Uiso 1 1 calc R . . C2 C -0.0435(6) 0.1813(5) -0.1312(3) 0.0568(13) Uani 1 1 d . . . H2A H -0.0976 0.1170 -0.1616 0.080 Uiso 1 1 calc R . . H2B H -0.0589 0.2711 -0.1528 0.080 Uiso 1 1 calc R . . C3 C -0.2770(5) 0.1643(5) -0.0291(3) 0.0540(12) Uani 1 1 d . . . H3 H -0.3004 0.0865 -0.0627 0.080 Uiso 1 1 calc R . . C4 C -0.3474(6) 0.1355(5) 0.0595(4) 0.0643(14) Uani 1 1 d . . . H4A H -0.4577 0.1408 0.0623 0.080 Uiso 1 1 calc R . . H4B H -0.3168 0.2071 0.0947 0.080 Uiso 1 1 calc R . . C5 C -0.3090(6) 0.0010(5) 0.0968(4) 0.0627(14) Uani 1 1 d . . . H5A H -0.3754 -0.0117 0.1495 0.080 Uiso 1 1 calc R . . H5B H -0.3306 -0.0711 0.0595 0.080 Uiso 1 1 calc R . . C6 C 0.1215(7) -0.0871(6) -0.1776(3) 0.0674(15) Uani 1 1 d . . . H6A H 0.0198 -0.0756 -0.1908 0.080 Uiso 1 1 calc R . . H6B H 0.1332 -0.1776 -0.1579 0.080 Uiso 1 1 calc R . . H6C H 0.1944 -0.0715 -0.2267 0.080 Uiso 1 1 calc R . . C7 C -0.0538(6) 0.2987(4) 0.0021(3) 0.0504(12) Uani 1 1 d . . . H7A H -0.1357 0.3285 0.0447 0.080 Uiso 1 1 calc R . . H7B H -0.0348 0.3703 -0.0392 0.080 Uiso 1 1 calc R . . C8 C 0.0883(5) 0.2776(4) 0.0417(3) 0.0440(10) Uani 1 1 d . . . C9 C -0.3511(7) 0.2882(6) -0.0641(4) 0.0756(18) Uani 1 1 d . . . H9A H -0.3510 0.3625 -0.0259 0.080 Uiso 1 1 calc R . . H9B H -0.4545 0.2669 -0.0712 0.080 Uiso 1 1 calc R . . H9C H -0.2941 0.3126 -0.1171 0.080 Uiso 1 1 calc R . . Cl1 Cl 0.30636(13) 0.49169(12) -0.21243(8) 0.0523(3) Uani 1 1 d . . . O3 O 0.3470(7) 0.6230(5) -0.2386(4) 0.124(2) Uani 1 1 d . . . O4 O 0.1538(8) 0.4865(7) -0.1810(6) 0.160(3) Uani 1 1 d . . . O5 O 0.3099(11) 0.4140(7) -0.2819(5) 0.184(4) Uani 1 1 d . . . O6 O 0.3898(12) 0.4475(11) -0.1588(8) 0.252(6) Uani 1 1 d . . . OW1 O 0.3534(4) 0.3511(4) 0.1536(3) 0.0778(12) Uani 1 1 d . . . H1OW H 0.3763 0.2752 0.1710 0.080 Uiso 1 1 d . . . H2OW H 0.4237 0.3980 0.1677 0.080 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 0.0331(4) 0.0224(4) 0.0347(4) 0.0010(3) -0.0044(3) 0.0008(3) N1 0.043(2) 0.044(2) 0.0430(19) 0.0032(16) 0.0025(16) -0.0012(16) N2 0.048(2) 0.0255(17) 0.052(2) 0.0007(15) -0.0175(17) 0.0031(15) O1 0.067(2) 0.0288(16) 0.102(3) -0.0056(17) -0.038(2) -0.0038(15) O2 0.0528(19) 0.0295(16) 0.069(2) -0.0031(14) -0.0221(16) 0.0009(13) C1 0.074(4) 0.052(3) 0.062(3) 0.018(2) 0.002(3) -0.007(3) C2 0.069(3) 0.043(3) 0.061(3) 0.014(2) -0.019(3) -0.003(2) C3 0.047(3) 0.039(2) 0.080(3) -0.005(2) -0.022(2) 0.001(2) C4 0.046(3) 0.058(3) 0.089(4) -0.011(3) -0.009(3) 0.010(2) C5 0.040(2) 0.066(3) 0.077(3) 0.005(3) 0.012(2) -0.001(2) C6 0.079(4) 0.063(3) 0.059(3) -0.010(3) -0.004(3) 0.011(3) C7 0.057(3) 0.025(2) 0.074(3) -0.002(2) -0.027(2) 0.0030(19) C8 0.046(2) 0.029(2) 0.059(3) -0.0009(19) -0.013(2) -0.0029(19) C9 0.069(4) 0.054(3) 0.114(5) -0.004(3) -0.046(4) 0.014(3) Cl1 0.0497(7) 0.0477(7) 0.0604(7) -0.0080(5) -0.0107(5) -0.0050(5) O3 0.143(5) 0.065(3) 0.169(6) 0.018(3) -0.036(4) -0.024(3) O4 0.085(4) 0.180(7) 0.199(8) 0.028(5) 0.033(5) -0.011(4) O5 0.252(10) 0.121(6) 0.165(6) -0.086(5) 0.012(6) -0.026(6) O6 0.258(10) 0.199(8) 0.357(15) 0.132(9) -0.242(11) -0.069(8) OW1 0.060(2) 0.076(3) 0.103(3) 0.003(2) -0.033(2) -0.0006(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.072(4) . ? Cu1 N1 2.072(4) 3 ? Cu1 N2 2.110(3) 3 ? Cu1 N2 2.110(3) . ? Cu1 O2 2.319(3) 3 ? Cu1 O2 2.320(3) . ? N1 C1 1.479(6) . ? N1 C5 1.479(7) 3 ? N1 C6 1.487(6) . ? N2 C7 1.490(5) . ? N2 C3 1.504(6) . ? N2 C2 1.510(6) . ? O1 C8 1.295(5) . ? O1 H1O1 1.110(3) . ? O2 C8 1.206(5) . ? C1 C2 1.497(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.504(8) . ? C3 C9 1.533(7) . ? C3 H3 0.9800 . ? C4 C5 1.518(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.479(7) 3 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.504(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cl1 O6 1.293(7) . ? Cl1 O5 1.356(6) . ? Cl1 O4 1.371(6) . ? Cl1 O3 1.396(5) . ? OW1 H1O1 1.436(4) . ? OW1 H1OW 0.837(4) . ? OW1 H2OW 0.833(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 N1 Cu1 N1 180.0 . 3 ? N1 Cu1 N2 93.10(14) . 3 ? N1 Cu1 N2 86.90(14) 3 3 ? N1 Cu1 N2 86.90(14) . . ? N1 Cu1 N2 93.10(14) 3 . ? N2 Cu1 N2 180.0 3 . ? N1 Cu1 O2 92.44(13) . 3 ? N1 Cu1 O2 87.56(13) 3 3 ? N2 Cu1 O2 78.82(12) 3 3 ? N2 Cu1 O2 101.18(12) . 3 ? N1 Cu1 O2 87.56(13) . . ? N1 Cu1 O2 92.44(13) 3 . ? N2 Cu1 O2 101.18(12) 3 . ? N2 Cu1 O2 78.82(12) . . ? O2 Cu1 O2 180.0 3 . ? C1 N1 C5 108.8(4) . 3 ? C1 N1 C6 107.4(4) . . ? C5 N1 C6 108.6(4) 3 . ? C1 N1 Cu1 104.4(3) . . ? C5 N1 Cu1 110.9(3) 3 . ? C6 N1 Cu1 116.4(3) . . ? C7 N2 C3 112.4(3) . . ? C7 N2 C2 108.6(4) . . ? C3 N2 C2 109.0(4) . . ? C7 N2 Cu1 111.1(2) . . ? C3 N2 Cu1 112.8(3) . . ? C2 N2 Cu1 102.3(3) . . ? C8 O1 H1O1 110.8(3) . . ? C8 O2 Cu1 109.9(3) . . ? N1 C1 C2 110.1(4) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? C1 C2 N2 109.5(4) . . ? C1 C2 H2A 109.8 . . ? N2 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? N2 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? N2 C3 C4 112.9(4) . . ? N2 C3 C9 112.2(4) . . ? C4 C3 C9 111.3(5) . . ? N2 C3 H3 106.7 . . ? C4 C3 H3 106.7 . . ? C9 C3 H3 106.7 . . ? C3 C4 C5 117.3(4) . . ? C3 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C3 C4 H4B 108.0 . . ? C5 C4 H4B 108.0 . . ? H4A C4 H4B 107.2 . . ? N1 C5 C4 114.2(4) 3 . ? N1 C5 H5A 108.7 3 . ? C4 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 3 . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 114.0(3) . . ? N2 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N2 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O2 C8 O1 124.4(4) . . ? O2 C8 C7 124.1(4) . . ? O1 C8 C7 111.5(4) . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O6 Cl1 O5 114.7(8) . . ? O6 Cl1 O4 111.3(7) . . ? O5 Cl1 O4 100.9(6) . . ? O6 Cl1 O3 111.8(5) . . ? O5 Cl1 O3 107.5(5) . . ? O4 Cl1 O3 110.1(4) . . ? H1O1 OW1 H1OW 124.4(4) . . ? H1O1 OW1 H2OW 134.1(4) . . ? H1OW OW1 H2OW 100.4(4) . . ?