# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 902070' #TrackingRef '1-2-3-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Co1 N4 O9' _chemical_formula_weight 559.48 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' Co Co 0.3494 0.9721 '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' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 9.042(2) _cell_length_b 8.6320(10) _cell_length_c 16.028(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.03(2) _cell_angle_gamma 90.00 _cell_volume 1238.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used 1830 _cell_measurement_theta_min 4.3225 _cell_measurement_theta_max 26.5931 _exptl_crystal_description ? _exptl_crystal_colour pink _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_absorpt_coefficient_mu 0.752 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11648 _diffrn_reflns_av_R_equivalents 0.1457 _diffrn_reflns_av_sigmaI/netI 0.2343 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 26.65 _reflns_number_total 2266 _reflns_number_gt 909 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SIR2004 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^ > 2\s(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^)+(0.1005P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2266 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2018 _refine_ls_R_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.2500 0.32053(14) 0.2500 0.0561(6) Uani 1 2 d S . . O1 O 0.1569(5) 0.1393(5) 0.3039(3) 0.0655(13) Uani 1 1 d . . . O2 O -0.0581(6) -0.0912(6) 0.2776(3) 0.0921(19) Uani 1 1 d . . . O3 O -0.0658(5) 0.2166(5) 0.4675(3) 0.0636(13) Uani 1 1 d . . . O1W O 0.3838(7) 0.9364(6) 0.3532(3) 0.107(2) Uani 1 1 d . . . O2W O 0.5288(11) 0.8516(11) 0.4999(6) 0.087(3) Uiso 0.50 1 d P . . N1 N 0.4517(6) 0.4408(6) 0.3077(3) 0.0582(16) Uani 1 1 d . . . N2 N 0.1670(7) 0.4537(6) 0.3668(3) 0.0536(15) Uani 1 1 d . . . C1 C 0.4339(8) 0.5004(9) 0.3922(4) 0.070(2) Uani 1 1 d . . . H1A H 0.5097 0.5782 0.4089 0.084 Uiso 1 1 calc R . . H1B H 0.4485 0.4164 0.4327 0.084 Uiso 1 1 calc R . . C2 C 0.2841(9) 0.5694(8) 0.3935(4) 0.071(2) Uani 1 1 d . . . H2A H 0.2751 0.6050 0.4500 0.085 Uiso 1 1 calc R . . H2B H 0.2715 0.6579 0.3559 0.085 Uiso 1 1 calc R . . C3 C 0.0240(9) 0.5287(7) 0.3372(4) 0.063(2) Uani 1 1 d . . . H3A H 0.0132 0.6205 0.3708 0.076 Uiso 1 1 calc R . . H3B H -0.0571 0.4585 0.3441 0.076 Uiso 1 1 calc R . . C4 C 0.5796(9) 0.3345(9) 0.3186(4) 0.076(2) Uani 1 1 d . . . H4A H 0.5954 0.2942 0.2647 0.114 Uiso 1 1 calc R . . H4B H 0.5599 0.2506 0.3548 0.114 Uiso 1 1 calc R . . H4C H 0.6673 0.3892 0.3434 0.114 Uiso 1 1 calc R . . C5 C 0.4845(9) 0.5742(8) 0.2556(5) 0.070(2) Uani 1 1 d . . . H5A H 0.5836 0.6133 0.2758 0.084 Uiso 1 1 calc R . . H5B H 0.4134 0.6565 0.2611 0.084 Uiso 1 1 calc R . . C6 C 0.1517(8) 0.3515(8) 0.4388(4) 0.065(2) Uani 1 1 d . . . H6A H 0.2482 0.3064 0.4592 0.078 Uiso 1 1 calc R . . H6B H 0.1208 0.4129 0.4840 0.078 Uiso 1 1 calc R . . C7 C 0.0428(7) 0.2263(8) 0.4169(4) 0.0520(18) Uani 1 1 d . . . C8 C 0.0480(9) 0.1266(7) 0.3520(4) 0.059(2) Uani 1 1 d . . . C9 C -0.0606(8) -0.0007(8) 0.3339(5) 0.066(2) Uani 1 1 d . . . C10 C -0.1672(8) 0.0005(9) 0.3930(5) 0.072(2) Uani 1 1 d . . . H10 H -0.2424 -0.0737 0.3880 0.086 Uiso 1 1 calc R . . C11 C -0.1609(9) 0.1048(10) 0.4547(5) 0.071(2) Uani 1 1 d . . . H11 H -0.2312 0.0963 0.4916 0.085 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 Co1 0.0757(11) 0.0442(8) 0.0533(9) 0.000 0.0265(7) 0.000 O1 0.074(3) 0.056(3) 0.075(3) 0.002(2) 0.037(3) 0.001(2) O2 0.113(5) 0.054(3) 0.122(5) -0.033(3) 0.059(4) -0.022(3) O3 0.072(3) 0.063(3) 0.064(3) 0.004(2) 0.041(3) -0.009(3) O1W 0.138(5) 0.075(4) 0.118(5) 0.036(3) 0.051(4) 0.024(4) N1 0.068(4) 0.059(4) 0.055(4) 0.000(3) 0.034(3) -0.002(3) N2 0.071(4) 0.044(3) 0.050(4) -0.007(3) 0.025(3) -0.003(3) C1 0.068(5) 0.083(5) 0.065(5) -0.022(4) 0.031(4) -0.021(5) C2 0.102(6) 0.055(4) 0.066(5) -0.023(4) 0.045(5) -0.020(5) C3 0.090(6) 0.043(4) 0.065(5) 0.002(4) 0.040(5) -0.005(4) C4 0.097(6) 0.083(5) 0.049(5) -0.005(4) 0.014(4) -0.008(5) C5 0.079(5) 0.055(5) 0.083(6) -0.002(4) 0.034(5) -0.005(4) C6 0.083(6) 0.067(5) 0.050(4) -0.007(4) 0.029(4) 0.005(4) C7 0.061(5) 0.056(5) 0.044(4) -0.001(3) 0.023(4) 0.002(4) C8 0.080(6) 0.035(4) 0.070(5) 0.013(4) 0.036(4) 0.018(4) C9 0.074(5) 0.035(4) 0.096(6) 0.011(4) 0.036(5) 0.004(4) C10 0.070(6) 0.058(5) 0.095(6) 0.007(5) 0.037(5) -0.001(4) C11 0.084(6) 0.067(5) 0.073(6) 0.018(5) 0.046(5) 0.011(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Co1 O1 2.026(4) 2 ? Co1 O1 2.026(4) . ? Co1 N1 2.188(6) . ? Co1 N1 2.188(5) 2 ? Co1 N2 2.404(5) 2 ? Co1 N2 2.404(5) . ? O1 C8 1.337(8) . ? O2 C9 1.196(8) . ? O3 C11 1.290(8) . ? O3 C7 1.360(7) . ? N1 C4 1.467(8) . ? N1 C1 1.478(8) . ? N1 C5 1.477(8) . ? N2 C3 1.464(8) . ? N2 C2 1.475(8) . ? N2 C6 1.475(7) . ? C1 C2 1.483(9) . ? C3 C5 1.531(8) 2 ? C5 C3 1.531(8) 2 ? C6 C7 1.471(8) . ? C7 C8 1.356(8) . ? C8 C9 1.474(10) . ? C9 C10 1.443(9) . ? C10 C11 1.332(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 O1 Co1 O1 78.9(2) 2 . ? O1 Co1 N1 100.08(19) 2 . ? O1 Co1 N1 123.87(19) . . ? O1 Co1 N1 123.87(19) 2 2 ? O1 Co1 N1 100.08(19) . 2 ? N1 Co1 N1 123.4(3) . 2 ? O1 Co1 N2 81.01(17) 2 2 ? O1 Co1 N2 153.46(18) . 2 ? N1 Co1 N2 76.7(2) . 2 ? N1 Co1 N2 77.09(19) 2 2 ? O1 Co1 N2 153.46(18) 2 . ? O1 Co1 N2 81.01(17) . . ? N1 Co1 N2 77.09(19) . . ? N1 Co1 N2 76.70(19) 2 . ? N2 Co1 N2 122.9(2) 2 . ? C8 O1 Co1 133.9(4) . . ? C11 O3 C7 118.2(6) . . ? C4 N1 C1 107.1(6) . . ? C4 N1 C5 109.7(5) . . ? C1 N1 C5 107.6(5) . . ? C4 N1 Co1 110.5(4) . . ? C1 N1 Co1 111.2(4) . . ? C5 N1 Co1 110.6(4) . . ? C3 N2 C2 111.1(5) . . ? C3 N2 C6 110.0(5) . . ? C2 N2 C6 108.6(5) . . ? C3 N2 Co1 108.5(4) . . ? C2 N2 Co1 105.1(4) . . ? C6 N2 Co1 113.4(4) . . ? N1 C1 C2 111.7(6) . . ? N2 C2 C1 110.2(5) . . ? N2 C3 C5 110.5(5) . 2 ? N1 C5 C3 111.3(5) . 2 ? C7 C6 N2 112.7(5) . . ? C8 C7 O3 121.6(7) . . ? C8 C7 C6 123.7(6) . . ? O3 C7 C6 114.7(6) . . ? O1 C8 C7 119.8(7) . . ? O1 C8 C9 118.2(6) . . ? C7 C8 C9 122.0(7) . . ? O2 C9 C10 125.8(7) . . ? O2 C9 C8 123.5(7) . . ? C10 C9 C8 110.7(7) . . ? C11 C10 C9 121.9(7) . . ? O3 C11 C10 125.6(7) . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.570 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.083 data_2 _database_code_depnum_ccdc_archive 'CCDC 902071' #TrackingRef '1-2-3-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H40 Co1 N6 O8' _chemical_formula_weight 623.58 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 17.662(5) _cell_length_b 8.804(5) _cell_length_c 18.188(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2828(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.2113 _cell_measurement_theta_max 24.4879 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 0.666 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2246 _diffrn_reflns_av_R_equivalents 0.1194 _diffrn_reflns_av_sigmaI/netI 0.0873 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 24.52 _reflns_number_total 2246 _reflns_number_gt 1441 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SIR2004 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^ > 2\s(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^)+(0.0928P)^2^+1.8195P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2246 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1218 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.48250(13) 0.2500 0.0326(4) Uani 1 2 d S . . O1 O 0.0399(2) 0.2998(4) 0.3081(2) 0.0295(10) Uani 1 1 d . . . O2 O 0.3203(3) 0.2697(6) 0.5154(2) 0.0461(14) Uani 1 1 d . . . O3 O 0.2484(3) 0.1026(6) 0.5679(3) 0.0554(14) Uani 1 1 d . . . O4 O 0.0750(4) 0.0635(7) 0.1848(4) 0.088(2) Uani 1 1 d . . . N1 N 0.0503(3) 0.5990(6) 0.1507(3) 0.0284(12) Uani 1 1 d . . . N2 N 0.1038(3) 0.6014(5) 0.2986(3) 0.0255(12) Uani 1 1 d . . . N3 N 0.2593(3) 0.1972(7) 0.5196(3) 0.0330(13) Uani 1 1 d . . . C1 C 0.1245(4) 0.6630(9) 0.1688(3) 0.0393(17) Uani 1 1 d . . . H1A H 0.1361 0.7449 0.1349 0.047 Uiso 1 1 calc R . . H1B H 0.1630 0.5853 0.1631 0.047 Uiso 1 1 calc R . . C2 C 0.1264(4) 0.7226(6) 0.2461(4) 0.0358(15) Uani 1 1 d . . . H2A H 0.1771 0.7576 0.2577 0.043 Uiso 1 1 calc R . . H2B H 0.0922 0.8081 0.2505 0.043 Uiso 1 1 calc R . . C3 C 0.0837(4) 0.6702(7) 0.3699(3) 0.0311(15) Uani 1 1 d . . . H3A H 0.1169 0.7556 0.3796 0.037 Uiso 1 1 calc R . . H3B H 0.0908 0.5961 0.4087 0.037 Uiso 1 1 calc R . . C4 C 0.0604(4) 0.4934(8) 0.0873(3) 0.0422(16) Uani 1 1 d . . . H4A H 0.0124 0.4499 0.0743 0.063 Uiso 1 1 calc R . . H4B H 0.0950 0.4140 0.1007 0.063 Uiso 1 1 calc R . . H4C H 0.0803 0.5485 0.0460 0.063 Uiso 1 1 calc R . . C5 C -0.0031(4) 0.7233(6) 0.1301(4) 0.0357(15) Uani 1 1 d . . . H5A H 0.0098 0.7607 0.0815 0.043 Uiso 1 1 calc R . . H5B H 0.0024 0.8066 0.1646 0.043 Uiso 1 1 calc R . . C6 C 0.1688(3) 0.4939(7) 0.3069(3) 0.0315(14) Uani 1 1 d . . . H6A H 0.2134 0.5514 0.3207 0.038 Uiso 1 1 calc R . . H6B H 0.1789 0.4473 0.2596 0.038 Uiso 1 1 calc R . . C7 C 0.1567(3) 0.3707(6) 0.3625(3) 0.0253(13) Uani 1 1 d . . . C8 C 0.0915(3) 0.2793(7) 0.3587(3) 0.0257(14) Uani 1 1 d . . . C9 C 0.0832(4) 0.1608(7) 0.4115(4) 0.0343(16) Uani 1 1 d . . . H9 H 0.0402 0.0999 0.4101 0.041 Uiso 1 1 calc R . . C10 C 0.1370(4) 0.1346(7) 0.4642(4) 0.0338(15) Uani 1 1 d . . . H10 H 0.1304 0.0575 0.4986 0.041 Uiso 1 1 calc R . . C11 C 0.2016(3) 0.2250(7) 0.4656(3) 0.0296(15) Uani 1 1 d . . . C12 C 0.2107(3) 0.3422(7) 0.4161(3) 0.0265(13) Uani 1 1 d . . . H12 H 0.2538 0.4029 0.4186 0.032 Uiso 1 1 calc R . . C13 C 0.1494(5) 0.1076(10) 0.1921(5) 0.064(2) 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 Co1 0.0343(6) 0.0324(7) 0.0312(7) 0.000 -0.0035(6) 0.000 O1 0.034(2) 0.022(2) 0.032(2) 0.0049(19) -0.014(2) -0.003(2) O2 0.038(3) 0.058(3) 0.042(3) 0.005(3) -0.015(2) -0.001(3) O3 0.054(3) 0.069(4) 0.043(3) 0.027(3) -0.012(3) 0.006(3) O4 0.068(4) 0.051(4) 0.146(7) -0.033(4) -0.042(4) 0.024(3) N1 0.027(3) 0.035(3) 0.022(3) 0.004(2) -0.005(2) -0.002(2) N2 0.030(3) 0.026(3) 0.021(3) 0.005(2) -0.007(2) -0.002(2) N3 0.038(3) 0.039(3) 0.022(3) 0.000(2) -0.006(2) 0.008(3) C1 0.034(4) 0.053(4) 0.031(4) 0.014(3) -0.002(3) -0.013(3) C2 0.036(3) 0.029(3) 0.043(4) 0.018(4) -0.011(3) -0.011(3) C3 0.037(4) 0.028(3) 0.028(4) -0.005(3) -0.004(3) -0.007(3) C4 0.044(4) 0.047(4) 0.035(4) 0.000(4) 0.003(3) 0.005(4) C5 0.047(4) 0.026(3) 0.034(4) 0.010(3) -0.006(4) -0.008(4) C6 0.029(3) 0.036(3) 0.030(3) 0.009(3) -0.002(3) -0.002(3) C7 0.026(3) 0.026(3) 0.023(3) 0.000(3) -0.002(3) 0.002(3) C8 0.028(3) 0.027(3) 0.022(3) 0.001(3) -0.004(3) 0.006(3) C9 0.031(3) 0.027(3) 0.045(4) 0.003(3) -0.009(3) -0.008(3) C10 0.035(3) 0.033(4) 0.033(4) 0.008(3) -0.005(3) 0.006(3) C11 0.033(3) 0.037(4) 0.019(3) 0.002(3) -0.009(3) 0.015(3) C12 0.025(3) 0.026(3) 0.028(3) -0.004(3) -0.006(3) 0.004(3) C13 0.066(6) 0.059(5) 0.067(6) 0.001(5) 0.004(5) 0.009(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Co1 O1 2.050(4) 4 ? Co1 O1 2.050(4) . ? Co1 N1 2.259(5) 4 ? Co1 N1 2.259(5) . ? Co1 N2 2.289(5) . ? Co1 N2 2.289(5) 4 ? O1 C8 1.308(7) . ? O2 N3 1.254(7) . ? O3 N3 1.226(7) . ? O4 C13 1.377(10) . ? N1 C1 1.464(8) . ? N1 C4 1.492(8) . ? N1 C5 1.492(8) . ? N2 C3 1.475(8) . ? N2 C2 1.487(7) . ? N2 C6 1.495(7) . ? N3 C11 1.437(8) . ? C1 C2 1.499(9) . ? C3 C5 1.498(9) 4 ? C5 C3 1.498(9) 4 ? C6 C7 1.497(8) . ? C7 C12 1.387(8) . ? C7 C8 1.407(8) . ? C8 C9 1.425(8) . ? C9 C10 1.370(8) . ? C10 C11 1.391(9) . ? C11 C12 1.379(8) . ? 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 O1 Co1 O1 76.6(2) 4 . ? O1 Co1 N1 129.32(18) 4 4 ? O1 Co1 N1 94.53(17) . 4 ? O1 Co1 N1 94.53(17) 4 . ? O1 Co1 N1 129.32(18) . . ? N1 Co1 N1 126.0(3) 4 . ? O1 Co1 N2 146.43(17) 4 . ? O1 Co1 N2 83.37(16) . . ? N1 Co1 N2 78.41(18) 4 . ? N1 Co1 N2 77.62(17) . . ? O1 Co1 N2 83.37(16) 4 4 ? O1 Co1 N2 146.43(17) . 4 ? N1 Co1 N2 77.62(17) 4 4 ? N1 Co1 N2 78.41(18) . 4 ? N2 Co1 N2 125.6(2) . 4 ? C8 O1 Co1 135.3(4) . . ? C1 N1 C4 107.9(5) . . ? C1 N1 C5 109.9(5) . . ? C4 N1 C5 109.8(5) . . ? C1 N1 Co1 110.3(3) . . ? C4 N1 Co1 112.5(4) . . ? C5 N1 Co1 106.6(4) . . ? C3 N2 C2 109.6(5) . . ? C3 N2 C6 110.9(5) . . ? C2 N2 C6 108.3(5) . . ? C3 N2 Co1 109.5(4) . . ? C2 N2 Co1 107.2(3) . . ? C6 N2 Co1 111.4(4) . . ? O3 N3 O2 121.6(5) . . ? O3 N3 C11 119.7(6) . . ? O2 N3 C11 118.7(5) . . ? N1 C1 C2 111.4(5) . . ? N2 C2 C1 110.2(5) . . ? N2 C3 C5 111.0(5) . 4 ? N1 C5 C3 111.8(5) . 4 ? N2 C6 C7 114.7(5) . . ? C12 C7 C8 119.6(5) . . ? C12 C7 C6 120.5(5) . . ? C8 C7 C6 119.9(5) . . ? O1 C8 C7 121.7(5) . . ? O1 C8 C9 120.2(5) . . ? C7 C8 C9 118.1(5) . . ? C10 C9 C8 121.6(6) . . ? C9 C10 C11 119.0(6) . . ? C12 C11 C10 120.9(6) . . ? C12 C11 N3 119.4(6) . . ? C10 C11 N3 119.8(6) . . ? C11 C12 C7 120.9(6) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 24.52 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.370 _refine_diff_density_min -1.000 _refine_diff_density_rms 0.097 data_3 _database_code_depnum_ccdc_archive 'CCDC 902072' #TrackingRef '1-2-3-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cl Co N4 Na O12' _chemical_formula_weight 663.90 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' Co Co 0.3494 0.9721 '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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.828(2) _cell_length_b 9.128(3) _cell_length_c 16.881(4) _cell_angle_alpha 91.84(2) _cell_angle_beta 94.77(2) _cell_angle_gamma 95.47(2) _cell_volume 1348.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2666 _cell_measurement_theta_min 3.8422 _cell_measurement_theta_max 26.0503 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 690 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96395 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET) (compiled Jul 10 2006,00:11:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9546 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.2149 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4221 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET) (compiled Jul 10 2006,00:11:42) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET) (compiled Jul 10 2006,00:11:42) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.2 (release 07-07-2006 CrysAlis171 .NET) (compiled Jul 10 2006,00:11:42) ; _computing_structure_solution 'SIR2004 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^ > 2\s(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^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4221 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 0.782 _refine_ls_restrained_S_all 0.782 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Na1 Na 0.68014(16) 0.96469(16) 0.39718(8) 0.0286(4) Uani 1 1 d . . . O1W O 0.6930(4) 1.1066(3) 0.50911(17) 0.0358(9) Uani 1 1 d . . . O2W O 0.9628(4) 1.2780(4) 0.4854(3) 0.0467(11) Uani 1 1 d . . . Co1 Co 0.37970(6) 0.85409(6) 0.25569(3) 0.02125(18) Uani 1 1 d . . . O1 O 0.4636(3) 0.7972(3) 0.36913(14) 0.0217(7) Uani 1 1 d . . . O2 O 0.7556(3) 0.7322(3) 0.42565(16) 0.0322(8) Uani 1 1 d . . . O3 O 0.4077(3) 0.4018(3) 0.38522(15) 0.0301(7) Uani 1 1 d . . . O4 O 0.5435(3) 1.0245(3) 0.28384(14) 0.0226(7) Uani 1 1 d . . . O5 O 0.8308(3) 1.1478(3) 0.33587(16) 0.0313(8) Uani 1 1 d . . . O6 O 0.6319(3) 1.2609(3) 0.12206(15) 0.0253(7) Uani 1 1 d . . . N1 N 0.1632(3) 0.9467(3) 0.26551(18) 0.0195(8) Uani 1 1 d . . . N2 N 0.2047(3) 0.6370(3) 0.26875(18) 0.0187(8) Uani 1 1 d . . . N3 N 0.4637(3) 0.6911(3) 0.17819(18) 0.0221(9) Uani 1 1 d . . . N4 N 0.3486(4) 0.9608(3) 0.13717(17) 0.0188(8) Uani 1 1 d . . . C1 C 0.0548(4) 0.8393(4) 0.3012(2) 0.0241(11) Uani 1 1 d . . . H1A H -0.0464 0.8729 0.2965 0.029 Uiso 1 1 calc R . . H1B H 0.0861 0.8322 0.3573 0.029 Uiso 1 1 calc R . . C2 C 0.0501(4) 0.6893(4) 0.2596(2) 0.0232(11) Uani 1 1 d . . . H2A H -0.0226 0.6202 0.2826 0.028 Uiso 1 1 calc R . . H2B H 0.0176 0.6956 0.2036 0.028 Uiso 1 1 calc R . . C3 C 0.2329(4) 0.5318(4) 0.2042(2) 0.0201(10) Uani 1 1 d . . . H3A H 0.1770 0.5554 0.1551 0.024 Uiso 1 1 calc R . . H3B H 0.1959 0.4328 0.2173 0.024 Uiso 1 1 calc R . . C4 C 0.4023(4) 0.5380(4) 0.1924(2) 0.0228(11) Uani 1 1 d . . . H4A H 0.4569 0.5033 0.2393 0.027 Uiso 1 1 calc R . . H4B H 0.4174 0.4740 0.1474 0.027 Uiso 1 1 calc R . . C5 C 0.4224(4) 0.7188(4) 0.0931(2) 0.0237(11) Uani 1 1 d . . . H5A H 0.3193 0.6753 0.0776 0.028 Uiso 1 1 calc R . . H5B H 0.4910 0.6728 0.0602 0.028 Uiso 1 1 calc R . . C6 C 0.4329(4) 0.8826(4) 0.0798(2) 0.0239(11) Uani 1 1 d . . . H6A H 0.5393 0.9223 0.0851 0.029 Uiso 1 1 calc R . . H6B H 0.3913 0.8988 0.0261 0.029 Uiso 1 1 calc R . . C7 C 0.1814(4) 0.9321(4) 0.1175(2) 0.0237(11) Uani 1 1 d . . . H7A H 0.1537 0.8270 0.1088 0.028 Uiso 1 1 calc R . . H7B H 0.1521 0.9802 0.0690 0.028 Uiso 1 1 calc R . . C8 C 0.0966(4) 0.9897(4) 0.1851(2) 0.0245(11) Uani 1 1 d . . . H8A H 0.1014 1.0962 0.1840 0.029 Uiso 1 1 calc R . . H8B H -0.0100 0.9510 0.1773 0.029 Uiso 1 1 calc R . . C9 C 0.1967(4) 1.0796(4) 0.3192(2) 0.0278(11) Uani 1 1 d . . . H9A H 0.2674 1.1492 0.2963 0.042 Uiso 1 1 calc R . . H9B H 0.2407 1.0524 0.3699 0.042 Uiso 1 1 calc R . . H9C H 0.1038 1.1234 0.3261 0.042 Uiso 1 1 calc R . . C10 C 0.6327(4) 0.7030(4) 0.1940(2) 0.0299(12) Uani 1 1 d . . . H10A H 0.6740 0.6350 0.1591 0.045 Uiso 1 1 calc R . . H10B H 0.6590 0.6802 0.2483 0.045 Uiso 1 1 calc R . . H10C H 0.6742 0.8015 0.1850 0.045 Uiso 1 1 calc R . . C11 C 0.2225(4) 0.5682(4) 0.3471(2) 0.0216(11) Uani 1 1 d . . . H11A H 0.1817 0.6296 0.3865 0.026 Uiso 1 1 calc R . . H11B H 0.1622 0.4733 0.3438 0.026 Uiso 1 1 calc R . . C12 C 0.3826(5) 0.5468(4) 0.3745(2) 0.0200(10) Uani 1 1 d . . . C13 C 0.4943(5) 0.6613(5) 0.3852(2) 0.0235(11) Uani 1 1 d . . . C14 C 0.6482(5) 0.6322(5) 0.4126(2) 0.0250(11) Uani 1 1 d . . . C15 C 0.6683(5) 0.4780(5) 0.4220(2) 0.0325(12) Uani 1 1 d . . . H15 H 0.7650 0.4509 0.4375 0.039 Uiso 1 1 calc R . . C16 C 0.5526(5) 0.3752(5) 0.4091(2) 0.0358(13) Uani 1 1 d . . . H16 H 0.5717 0.2780 0.4169 0.043 Uiso 1 1 calc R . . C17 C 0.3951(4) 1.1218(4) 0.1349(2) 0.0232(11) Uani 1 1 d . . . H17A H 0.3849 1.1511 0.0801 0.028 Uiso 1 1 calc R . . H17B H 0.3263 1.1750 0.1642 0.028 Uiso 1 1 calc R . . C18 C 0.5543(4) 1.1643(4) 0.1689(2) 0.0188(11) Uani 1 1 d . . . C19 C 0.6160(5) 1.1201(4) 0.2393(2) 0.0224(11) Uani 1 1 d . . . C20 C 0.7711(5) 1.1836(4) 0.2695(3) 0.0222(11) Uani 1 1 d . . . C21 C 0.8411(4) 1.2844(4) 0.2181(3) 0.0306(12) Uani 1 1 d . . . H21 H 0.9386 1.3289 0.2339 0.037 Uiso 1 1 calc R . . C22 C 0.7739(5) 1.3187(4) 0.1481(3) 0.0315(12) Uani 1 1 d . . . H22 H 0.8267 1.3842 0.1166 0.038 Uiso 1 1 calc R . . Cl1 Cl -0.14135(12) 0.69155(12) 0.00931(6) 0.0274(3) Uani 1 1 d . . . O11 O -0.0388(3) 0.6239(3) 0.06393(15) 0.0411(8) Uani 1 1 d . . . O12 O -0.0731(3) 0.7212(3) -0.06308(15) 0.0427(9) Uani 1 1 d . . . O13 O -0.1809(3) 0.8282(3) 0.04525(15) 0.0343(8) Uani 1 1 d . . . O14 O -0.2782(3) 0.5922(3) -0.00824(16) 0.0424(8) Uani 1 1 d . . . H11W H 0.795(5) 1.162(4) 0.505(2) 0.066(17) Uiso 1 1 d . . . H12W H 0.627(6) 1.128(5) 0.557(3) 0.13(2) Uiso 1 1 d . . . H21W H 1.050(6) 1.289(6) 0.515(3) 0.12(3) Uiso 1 1 d . . . H22W H 0.970(7) 1.254(7) 0.439(3) 0.13(3) 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 Na1 0.0278(10) 0.0308(10) 0.0264(10) -0.0005(8) -0.0003(8) 0.0011(8) O1W 0.035(2) 0.042(2) 0.031(2) 0.0001(17) 0.0064(18) 0.0011(18) O2W 0.028(2) 0.075(3) 0.036(3) -0.003(2) -0.006(2) 0.011(2) Co1 0.0182(4) 0.0238(4) 0.0221(4) 0.0005(3) 0.0028(3) 0.0033(3) O1 0.0255(18) 0.0201(17) 0.0204(17) 0.0040(15) 0.0026(14) 0.0059(14) O2 0.022(2) 0.0340(19) 0.041(2) 0.0040(17) -0.0047(16) 0.0070(16) O3 0.039(2) 0.0232(19) 0.0271(18) 0.0052(15) -0.0010(15) 0.0022(15) O4 0.0214(18) 0.0268(17) 0.0192(16) 0.0047(14) 0.0017(14) -0.0011(14) O5 0.0256(19) 0.042(2) 0.0257(18) 0.0023(17) -0.0005(15) 0.0027(15) O6 0.0197(18) 0.0265(17) 0.0292(18) 0.0081(15) 0.0018(15) -0.0025(14) N1 0.019(2) 0.018(2) 0.021(2) -0.0010(19) -0.0009(17) 0.0058(17) N2 0.019(2) 0.024(2) 0.015(2) 0.0034(18) 0.0050(17) 0.0062(17) N3 0.018(2) 0.023(2) 0.025(2) 0.0045(18) 0.0026(18) 0.0010(17) N4 0.020(2) 0.017(2) 0.019(2) 0.0003(18) -0.0019(18) 0.0019(17) C1 0.017(3) 0.027(3) 0.028(3) 0.000(2) 0.005(2) 0.002(2) C2 0.016(3) 0.031(3) 0.025(3) 0.004(2) 0.010(2) 0.002(2) C3 0.024(3) 0.021(2) 0.015(2) 0.002(2) 0.001(2) 0.002(2) C4 0.025(3) 0.022(3) 0.022(3) 0.001(2) 0.004(2) 0.003(2) C5 0.023(3) 0.031(3) 0.018(3) -0.002(2) -0.001(2) 0.009(2) C6 0.025(3) 0.030(3) 0.017(2) 0.002(2) 0.003(2) 0.002(2) C7 0.026(3) 0.022(3) 0.023(3) 0.003(2) 0.001(2) -0.001(2) C8 0.016(3) 0.027(3) 0.030(3) 0.004(2) -0.004(2) 0.002(2) C9 0.022(3) 0.028(3) 0.033(3) -0.004(2) 0.004(2) 0.002(2) C10 0.022(3) 0.041(3) 0.026(3) -0.003(2) 0.005(2) 0.003(2) C11 0.022(3) 0.022(3) 0.019(3) 0.002(2) 0.001(2) -0.002(2) C12 0.021(3) 0.019(3) 0.020(3) 0.001(2) 0.001(2) 0.002(2) C13 0.020(3) 0.039(3) 0.013(3) 0.000(2) 0.006(2) 0.007(3) C14 0.027(3) 0.035(3) 0.014(3) -0.004(2) 0.006(2) 0.007(3) C15 0.031(3) 0.033(3) 0.034(3) -0.004(3) 0.002(2) 0.011(3) C16 0.042(4) 0.036(3) 0.034(3) 0.013(3) 0.000(3) 0.027(3) C17 0.027(3) 0.022(3) 0.022(3) 0.004(2) 0.006(2) 0.004(2) C18 0.018(3) 0.015(3) 0.024(3) 0.003(2) 0.009(2) -0.004(2) C19 0.022(3) 0.030(3) 0.016(3) 0.001(2) 0.004(2) 0.007(2) C20 0.018(3) 0.022(3) 0.026(3) -0.009(3) 0.004(2) 0.000(2) C21 0.018(3) 0.029(3) 0.043(3) 0.006(3) -0.002(3) -0.002(2) C22 0.017(3) 0.026(3) 0.053(4) 0.007(3) 0.013(3) -0.002(2) Cl1 0.0257(8) 0.0332(7) 0.0230(7) 0.0027(6) 0.0005(6) 0.0023(6) O11 0.043(2) 0.0391(19) 0.0379(19) 0.0050(17) -0.0254(16) 0.0107(16) O12 0.057(2) 0.050(2) 0.0284(18) 0.0099(16) 0.0258(17) 0.0169(17) O13 0.044(2) 0.0255(18) 0.0340(19) -0.0046(16) 0.0079(15) 0.0065(15) O14 0.0246(19) 0.045(2) 0.054(2) -0.0125(17) -0.0029(16) -0.0076(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Na1 O1W 2.245(3) . ? Na1 O4 2.285(3) . ? Na1 O1 2.337(3) . ? Na1 O2 2.337(3) . ? Na1 O5 2.356(3) . ? Na1 C14 3.042(5) . ? Na1 C13 3.073(5) . ? Na1 C20 3.088(5) . ? Na1 C19 3.095(4) . ? Na1 Co1 3.4698(18) . ? Co1 O4 2.036(3) . ? Co1 O1 2.094(2) . ? Co1 N3 2.173(3) . ? Co1 N1 2.179(3) . ? Co1 N4 2.261(3) . ? Co1 N2 2.421(3) . ? O1 C13 1.326(4) . ? O2 C14 1.252(4) . ? O3 C16 1.356(4) . ? O3 C12 1.377(4) . ? O4 C19 1.324(4) . ? O5 C20 1.264(4) . ? O6 C22 1.346(4) . ? O6 C18 1.375(4) . ? N1 C1 1.481(4) . ? N1 C9 1.482(4) . ? N1 C8 1.512(4) . ? N2 C3 1.481(4) . ? N2 C11 1.486(4) . ? N2 C2 1.486(4) . ? N3 C4 1.484(4) . ? N3 C10 1.486(4) . ? N3 C5 1.489(4) . ? N4 C6 1.476(4) . ? N4 C7 1.483(4) . ? N4 C17 1.490(4) . ? C1 C2 1.514(4) . ? C3 C4 1.521(4) . ? C5 C6 1.514(4) . ? C7 C8 1.522(4) . ? C11 C12 1.483(4) . ? C12 C13 1.364(5) . ? C13 C14 1.450(5) . ? C14 C15 1.448(5) . ? C15 C16 1.318(5) . ? C17 C18 1.484(5) . ? C18 C19 1.356(5) . ? C19 C20 1.478(5) . ? C20 C21 1.420(5) . ? C21 C22 1.337(5) . ? Cl1 O12 1.429(2) . ? Cl1 O11 1.434(2) . ? Cl1 O14 1.443(3) . ? Cl1 O13 1.454(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 O1W Na1 O4 121.08(11) . . ? O1W Na1 O1 117.50(12) . . ? O4 Na1 O1 69.58(9) . . ? O1W Na1 O2 110.36(11) . . ? O4 Na1 O2 126.07(12) . . ? O1 Na1 O2 73.53(10) . . ? O1W Na1 O5 90.86(12) . . ? O4 Na1 O5 72.27(10) . . ? O1 Na1 O5 140.48(11) . . ? O2 Na1 O5 124.11(11) . . ? O1W Na1 C14 117.84(12) . . ? O4 Na1 C14 109.81(12) . . ? O1 Na1 C14 51.16(10) . . ? O2 Na1 C14 22.37(9) . . ? O5 Na1 C14 139.54(11) . . ? O1W Na1 C13 120.37(12) . . ? O4 Na1 C13 88.58(11) . . ? O1 Na1 C13 23.75(8) . . ? O2 Na1 C13 49.79(10) . . ? O5 Na1 C13 148.73(11) . . ? C14 Na1 C13 27.42(10) . . ? O1W Na1 C20 103.76(12) . . ? O4 Na1 C20 50.33(10) . . ? O1 Na1 C20 118.78(11) . . ? O2 Na1 C20 131.66(11) . . ? O5 Na1 C20 22.01(9) . . ? C14 Na1 C20 136.89(11) . . ? C13 Na1 C20 131.99(12) . . ? O1W Na1 C19 116.20(11) . . ? O4 Na1 C19 22.70(9) . . ? O1 Na1 C19 91.62(11) . . ? O2 Na1 C19 132.73(11) . . ? O5 Na1 C19 49.64(10) . . ? C14 Na1 C19 124.15(12) . . ? C13 Na1 C19 108.31(12) . . ? C20 Na1 C19 27.65(10) . . ? O1W Na1 Co1 131.71(10) . . ? O4 Na1 Co1 34.20(7) . . ? O1 Na1 Co1 36.04(6) . . ? O2 Na1 Co1 98.18(9) . . ? O5 Na1 Co1 104.61(8) . . ? C14 Na1 Co1 78.11(9) . . ? C13 Na1 Co1 54.55(8) . . ? C20 Na1 Co1 82.76(9) . . ? C19 Na1 Co1 55.64(8) . . ? O4 Co1 O1 79.34(10) . . ? O4 Co1 N3 110.54(11) . . ? O1 Co1 N3 102.81(11) . . ? O4 Co1 N1 105.29(11) . . ? O1 Co1 N1 108.49(11) . . ? N3 Co1 N1 135.85(12) . . ? O4 Co1 N4 84.89(10) . . ? O1 Co1 N4 163.86(10) . . ? N3 Co1 N4 79.50(11) . . ? N1 Co1 N4 78.88(11) . . ? O4 Co1 N2 160.78(10) . . ? O1 Co1 N2 81.75(10) . . ? N3 Co1 N2 77.02(11) . . ? N1 Co1 N2 77.53(11) . . ? N4 Co1 N2 114.18(11) . . ? O4 Co1 Na1 39.11(7) . . ? O1 Co1 Na1 41.02(7) . . ? N3 Co1 Na1 105.84(9) . . ? N1 Co1 Na1 118.24(9) . . ? N4 Co1 Na1 122.86(8) . . ? N2 Co1 Na1 122.54(8) . . ? C13 O1 Co1 122.3(2) . . ? C13 O1 Na1 111.0(2) . . ? Co1 O1 Na1 102.94(10) . . ? C14 O2 Na1 112.4(3) . . ? C16 O3 C12 116.6(3) . . ? C19 O4 Co1 131.9(2) . . ? C19 O4 Na1 115.5(2) . . ? Co1 O4 Na1 106.69(11) . . ? C20 O5 Na1 113.7(3) . . ? C22 O6 C18 118.9(3) . . ? C1 N1 C9 109.3(3) . . ? C1 N1 C8 110.6(3) . . ? C9 N1 C8 109.6(3) . . ? C1 N1 Co1 109.9(2) . . ? C9 N1 Co1 106.5(2) . . ? C8 N1 Co1 110.9(2) . . ? C3 N2 C11 110.4(3) . . ? C3 N2 C2 113.4(3) . . ? C11 N2 C2 107.9(3) . . ? C3 N2 Co1 105.8(2) . . ? C11 N2 Co1 114.4(2) . . ? C2 N2 Co1 105.0(2) . . ? C4 N3 C10 108.5(3) . . ? C4 N3 C5 107.4(3) . . ? C10 N3 C5 109.6(3) . . ? C4 N3 Co1 113.1(2) . . ? C10 N3 Co1 107.3(2) . . ? C5 N3 Co1 110.9(2) . . ? C6 N4 C7 111.0(3) . . ? C6 N4 C17 108.6(3) . . ? C7 N4 C17 109.5(3) . . ? C6 N4 Co1 108.1(2) . . ? C7 N4 Co1 101.8(2) . . ? C17 N4 Co1 117.6(2) . . ? N1 C1 C2 110.4(3) . . ? N2 C2 C1 109.2(3) . . ? N2 C3 C4 110.9(3) . . ? N3 C4 C3 110.3(3) . . ? N3 C5 C6 110.6(3) . . ? N4 C6 C5 111.5(3) . . ? N4 C7 C8 110.2(3) . . ? N1 C8 C7 112.1(3) . . ? C12 C11 N2 114.1(3) . . ? C13 C12 O3 123.8(4) . . ? C13 C12 C11 122.1(4) . . ? O3 C12 C11 114.0(3) . . ? O1 C13 C12 120.6(4) . . ? O1 C13 C14 120.3(4) . . ? C12 C13 C14 119.1(4) . . ? O1 C13 Na1 45.20(18) . . ? C12 C13 Na1 165.7(3) . . ? C14 C13 Na1 75.1(3) . . ? O2 C14 C15 122.7(4) . . ? O2 C14 C13 122.7(4) . . ? C15 C14 C13 114.6(4) . . ? O2 C14 Na1 45.3(2) . . ? C15 C14 Na1 167.7(3) . . ? C13 C14 Na1 77.5(3) . . ? C16 C15 C14 121.4(4) . . ? C15 C16 O3 124.3(4) . . ? C18 C17 N4 113.2(3) . . ? C19 C18 O6 123.1(4) . . ? C19 C18 C17 125.0(3) . . ? O6 C18 C17 111.9(3) . . ? O4 C19 C18 123.5(4) . . ? O4 C19 C20 117.6(4) . . ? C18 C19 C20 118.9(4) . . ? O4 C19 Na1 41.77(18) . . ? C18 C19 Na1 165.2(3) . . ? C20 C19 Na1 75.9(2) . . ? O5 C20 C21 125.3(4) . . ? O5 C20 C19 120.7(4) . . ? C21 C20 C19 114.1(4) . . ? O5 C20 Na1 44.32(19) . . ? C21 C20 Na1 169.2(3) . . ? C19 C20 Na1 76.4(2) . . ? C22 C21 C20 123.3(4) . . ? C21 C22 O6 121.7(4) . . ? O12 Cl1 O11 110.66(16) . . ? O12 Cl1 O14 108.92(17) . . ? O11 Cl1 O14 108.71(16) . . ? O12 Cl1 O13 109.64(15) . . ? O11 Cl1 O13 109.59(16) . . ? O14 Cl1 O13 109.29(16) . . ? _diffrn_measured_fraction_theta_max 0.790 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.457 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.070 data_4 _database_code_depnum_ccdc_archive 'CCDC 902073' #TrackingRef '1-2-3-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H76 Cl4 Cu4 N8 O36' _chemical_formula_weight 1689.09 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.374(2) _cell_length_b 11.780(2) _cell_length_c 15.774(2) _cell_angle_alpha 88.910(10) _cell_angle_beta 90.17(2) _cell_angle_gamma 69.82(2) _cell_volume 1634.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 200 _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.3178 _cell_measurement_theta_max 28.5180 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.549 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.4682 _exptl_absorpt_correction_T_max 0.7450 _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17587 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 28.58 _reflns_number_total 7221 _reflns_number_gt 5091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR2004 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^ > 2\s(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^)+(0.1408P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7221 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 0.801 _refine_ls_restrained_S_all 0.801 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.07132(3) 0.21565(3) 0.21577(2) 0.02526(11) Uani 1 1 d . . . Cu2 Cu -0.31331(4) 0.18624(3) 0.14146(2) 0.02905(11) Uani 1 1 d . . . Cl1 Cl -0.29053(9) -0.25941(7) 0.15726(5) 0.0426(2) Uani 1 1 d . . . Cl2 Cl -0.85985(10) 0.69378(7) 0.41708(5) 0.0440(2) Uani 1 1 d . . . O6 O 0.2502(2) -0.22701(18) 0.17249(13) 0.0363(5) Uani 1 1 d . . . O4 O 0.2160(2) -0.10527(16) -0.04198(12) 0.0294(4) Uani 1 1 d . . . O5 O 0.4085(2) -0.32574(17) -0.06323(13) 0.0344(5) Uani 1 1 d . . . O3 O -0.3025(2) 0.50351(17) 0.36194(13) 0.0339(5) Uani 1 1 d . . . O1 O -0.1661(2) 0.27368(16) 0.20352(12) 0.0283(4) Uani 1 1 d . . . O2 O -0.4446(2) 0.26529(18) 0.23624(13) 0.0335(5) Uani 1 1 d . . . O7 O -0.1582(4) -0.2355(4) 0.1795(3) 0.1050(13) Uani 1 1 d . . . O8 O -0.2500(3) -0.3671(2) 0.10875(16) 0.0510(6) Uani 1 1 d . . . O9 O -0.3672(3) -0.2740(2) 0.23261(16) 0.0556(6) Uani 1 1 d . . . O10 O -0.3917(4) -0.1605(3) 0.1084(2) 0.0997(12) Uani 1 1 d . . . O11 O -0.7979(5) 0.6742(4) 0.3385(2) 0.1284(16) Uani 1 1 d . . . O12 O -0.7590(4) 0.6932(4) 0.4848(2) 0.0963(11) Uani 1 1 d . . . O13 O -0.9048(10) 0.5993(7) 0.4313(4) 0.224(4) Uani 1 1 d . . . O14 O -0.9855(5) 0.7947(5) 0.4212(3) 0.158(2) Uani 1 1 d . . . O1W O -0.2554(2) 0.03213(18) 0.20721(14) 0.0393(5) Uani 1 1 d . . . O2W O -0.3954(3) 0.0260(2) 0.35150(16) 0.0523(6) Uani 1 1 d . . . O3W O -0.2994(3) 0.7798(2) 0.40017(16) 0.0568(7) Uani 1 1 d . . . O4W O -0.5437(4) 0.8186(3) 0.5141(2) 0.0877(10) Uani 1 1 d . . . N4 N 0.1938(3) 0.0572(2) 0.15819(15) 0.0282(5) Uani 1 1 d . . . N1 N 0.1321(3) 0.3011(2) 0.11604(15) 0.0293(5) Uani 1 1 d . . . N2 N 0.0653(3) 0.3636(2) 0.28536(16) 0.0308(5) Uani 1 1 d . . . N3 N 0.1240(3) 0.1181(2) 0.32829(16) 0.0335(6) Uani 1 1 d . . . C7 C 0.2685(3) 0.0879(3) 0.08160(19) 0.0319(6) Uani 1 1 d . . . H1A H 0.2084 0.0883 0.0314 0.038 Uiso 1 1 calc R . . H1B H 0.3684 0.0272 0.0748 0.038 Uiso 1 1 calc R . . C8 C 0.2834(3) 0.2109(3) 0.0912(2) 0.0349(7) Uani 1 1 d . . . H2A H 0.3591 0.2065 0.1344 0.042 Uiso 1 1 calc R . . H2B H 0.3160 0.2365 0.0381 0.042 Uiso 1 1 calc R . . C1 C 0.1548(4) 0.4123(3) 0.1469(2) 0.0432(8) Uani 1 1 d . . . H3A H 0.0648 0.4822 0.1346 0.052 Uiso 1 1 calc R . . H3B H 0.2400 0.4240 0.1179 0.052 Uiso 1 1 calc R . . C2 C 0.1852(3) 0.4011(3) 0.2412(2) 0.0403(8) Uani 1 1 d . . . H4A H 0.1842 0.4780 0.2626 0.048 Uiso 1 1 calc R . . H4B H 0.2848 0.3413 0.2527 0.048 Uiso 1 1 calc R . . C3 C 0.1071(4) 0.3195(3) 0.3748(2) 0.0396(7) Uani 1 1 d . . . H5A H 0.0156 0.3324 0.4075 0.048 Uiso 1 1 calc R . . H5B H 0.1645 0.3647 0.4005 0.048 Uiso 1 1 calc R . . C4 C 0.2005(4) 0.1877(3) 0.3759(2) 0.0430(8) Uani 1 1 d . . . H6A H 0.2988 0.1765 0.3510 0.052 Uiso 1 1 calc R . . H6B H 0.2173 0.1576 0.4341 0.052 Uiso 1 1 calc R . . C5 C 0.2338(3) -0.0037(3) 0.3082(2) 0.0363(7) Uani 1 1 d . . . H7A H 0.1804 -0.0608 0.3038 0.044 Uiso 1 1 calc R . . H7B H 0.3088 -0.0318 0.3535 0.044 Uiso 1 1 calc R . . C6 C 0.3114(3) 0.0025(3) 0.22634(19) 0.0334(7) Uani 1 1 d . . . H8A H 0.3755 -0.0781 0.2105 0.040 Uiso 1 1 calc R . . H8B H 0.3753 0.0514 0.2329 0.040 Uiso 1 1 calc R . . C9 C 0.0198(3) 0.3305(3) 0.0452(2) 0.0390(7) Uani 1 1 d . . . H9A H -0.0741 0.3889 0.0634 0.059 Uiso 1 1 calc R . . H9B H 0.0026 0.2583 0.0285 0.059 Uiso 1 1 calc R . . H9C H 0.0584 0.3632 -0.0020 0.059 Uiso 1 1 calc R . . C10 C -0.0057(4) 0.1060(3) 0.3760(2) 0.0424(8) Uani 1 1 d . . . H10A H -0.0541 0.0615 0.3433 0.064 Uiso 1 1 calc R . . H10B H -0.0774 0.1849 0.3870 0.064 Uiso 1 1 calc R . . H10C H 0.0303 0.0637 0.4288 0.064 Uiso 1 1 calc R . . C11 C 0.1086(3) -0.0239(2) 0.13459(18) 0.0279(6) Uani 1 1 d . . . H11A H 0.0366 0.0153 0.0897 0.033 Uiso 1 1 calc R . . H11B H 0.0511 -0.0345 0.1832 0.033 Uiso 1 1 calc R . . C12 C 0.2071(3) -0.1455(2) 0.10573(18) 0.0274(6) Uani 1 1 d . . . C13 C 0.2545(3) -0.1781(2) 0.02539(18) 0.0275(6) Uani 1 1 d . . . C14 C 0.3591(3) -0.2989(2) 0.01242(18) 0.0281(6) Uani 1 1 d . . . C15 C 0.3997(4) -0.3794(3) 0.0831(2) 0.0378(7) Uani 1 1 d . . . H15 H 0.4640 -0.4588 0.0766 0.045 Uiso 1 1 calc R . . C16 C 0.3451(3) -0.3404(3) 0.1595(2) 0.0389(7) Uani 1 1 d . . . H16 H 0.3739 -0.3940 0.2056 0.047 Uiso 1 1 calc R . . C17 C -0.0790(3) 0.4687(3) 0.2821(2) 0.0358(7) Uani 1 1 d . . . H17A H -0.0731 0.5282 0.3224 0.043 Uiso 1 1 calc R . . H17B H -0.0922 0.5060 0.2259 0.043 Uiso 1 1 calc R . . C18 C -0.2118(3) 0.4330(2) 0.30192(19) 0.0308(6) Uani 1 1 d . . . C19 C -0.2510(3) 0.3456(2) 0.26024(17) 0.0269(6) Uani 1 1 d . . . C20 C -0.3984(3) 0.3372(2) 0.27880(18) 0.0279(6) Uani 1 1 d . . . C21 C -0.4852(3) 0.4116(3) 0.34311(19) 0.0345(7) Uani 1 1 d . . . H21 H -0.5775 0.4051 0.3592 0.041 Uiso 1 1 calc R . . C22 C -0.4341(3) 0.4914(3) 0.38072(19) 0.0338(7) Uani 1 1 d . . . H22 H -0.4938 0.5405 0.4220 0.041 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 0.02380(18) 0.02546(18) 0.02462(19) -0.00576(13) 0.00110(14) -0.00580(13) Cu2 0.02763(19) 0.0311(2) 0.0273(2) -0.00758(15) 0.00241(15) -0.00840(15) Cl1 0.0448(4) 0.0367(4) 0.0428(5) -0.0055(3) 0.0068(4) -0.0092(3) Cl2 0.0509(5) 0.0442(4) 0.0379(4) -0.0099(3) 0.0077(4) -0.0172(4) O6 0.0440(12) 0.0329(11) 0.0300(11) -0.0030(9) 0.0026(10) -0.0105(9) O4 0.0307(10) 0.0265(10) 0.0268(10) -0.0055(8) -0.0003(8) -0.0042(8) O5 0.0319(11) 0.0331(11) 0.0335(12) -0.0067(9) 0.0011(9) -0.0050(9) O3 0.0330(11) 0.0325(11) 0.0336(11) -0.0104(9) 0.0043(9) -0.0073(9) O1 0.0257(9) 0.0287(10) 0.0299(11) -0.0091(8) 0.0034(8) -0.0083(8) O2 0.0298(10) 0.0379(11) 0.0335(11) -0.0096(9) 0.0041(9) -0.0122(9) O7 0.082(2) 0.123(3) 0.131(3) -0.046(3) 0.027(2) -0.061(2) O8 0.0553(14) 0.0428(13) 0.0521(15) -0.0119(11) 0.0111(12) -0.0125(11) O9 0.0636(16) 0.0598(16) 0.0389(14) -0.0071(12) 0.0072(12) -0.0151(13) O10 0.119(3) 0.071(2) 0.065(2) 0.0100(17) 0.0244(19) 0.0229(19) O11 0.138(3) 0.148(4) 0.062(2) -0.007(2) 0.028(2) 0.000(3) O12 0.078(2) 0.124(3) 0.083(3) -0.019(2) -0.0040(19) -0.030(2) O13 0.422(11) 0.242(7) 0.116(4) 0.002(4) 0.006(5) -0.252(8) O14 0.100(3) 0.166(5) 0.144(4) -0.075(4) -0.031(3) 0.040(3) O1W 0.0464(12) 0.0353(11) 0.0362(12) -0.0028(9) 0.0055(10) -0.0138(10) O2W 0.0576(15) 0.0534(15) 0.0454(15) -0.0019(12) 0.0086(12) -0.0184(12) O3W 0.0631(16) 0.0554(15) 0.0493(15) -0.0093(12) 0.0030(13) -0.0166(13) O4W 0.112(3) 0.104(3) 0.069(2) -0.0321(19) 0.0259(19) -0.064(2) N4 0.0276(12) 0.0291(12) 0.0255(12) -0.0051(10) 0.0012(10) -0.0065(10) N1 0.0267(12) 0.0288(12) 0.0335(13) -0.0054(10) 0.0024(10) -0.0108(10) N2 0.0269(12) 0.0346(13) 0.0319(13) -0.0091(11) 0.0012(10) -0.0115(10) N3 0.0328(13) 0.0330(13) 0.0299(13) -0.0077(11) -0.0006(11) -0.0048(10) C7 0.0315(15) 0.0322(15) 0.0296(16) -0.0050(12) 0.0030(13) -0.0076(12) C8 0.0284(15) 0.0402(16) 0.0355(17) -0.0044(13) 0.0046(13) -0.0108(13) C1 0.0414(18) 0.0377(17) 0.054(2) -0.0080(15) 0.0106(16) -0.0171(14) C2 0.0311(16) 0.0360(16) 0.055(2) -0.0183(15) 0.0034(15) -0.0115(13) C3 0.0389(17) 0.0402(17) 0.0373(18) -0.0102(14) -0.0051(14) -0.0099(14) C4 0.0419(18) 0.0505(19) 0.0317(17) -0.0107(15) -0.0078(15) -0.0093(15) C5 0.0366(16) 0.0337(16) 0.0322(17) -0.0030(13) -0.0027(14) -0.0037(13) C6 0.0297(15) 0.0335(15) 0.0318(16) -0.0077(12) -0.0030(13) -0.0041(12) C9 0.0361(17) 0.0394(17) 0.0375(18) 0.0025(14) 0.0027(14) -0.0081(13) C10 0.0469(19) 0.0446(18) 0.0305(17) -0.0022(14) 0.0079(15) -0.0090(15) C11 0.0247(14) 0.0295(14) 0.0272(15) -0.0065(11) 0.0043(11) -0.0063(11) C12 0.0290(14) 0.0250(13) 0.0269(15) -0.0016(11) 0.0003(12) -0.0075(11) C13 0.0256(14) 0.0268(14) 0.0290(15) -0.0038(11) -0.0005(12) -0.0075(11) C14 0.0251(14) 0.0285(14) 0.0307(15) -0.0064(12) -0.0002(12) -0.0089(11) C15 0.0412(17) 0.0273(15) 0.0425(18) -0.0060(13) 0.0018(15) -0.0083(13) C16 0.0438(18) 0.0319(15) 0.0388(18) -0.0023(13) 0.0019(15) -0.0100(14) C17 0.0322(15) 0.0287(14) 0.0438(18) -0.0110(13) 0.0038(14) -0.0064(12) C18 0.0301(15) 0.0276(14) 0.0310(15) -0.0066(12) 0.0000(12) -0.0051(11) C19 0.0267(14) 0.0267(13) 0.0237(14) -0.0019(11) -0.0003(11) -0.0046(11) C20 0.0248(14) 0.0310(14) 0.0267(15) -0.0044(12) 0.0006(12) -0.0080(11) C21 0.0296(15) 0.0393(16) 0.0318(16) -0.0073(13) 0.0044(13) -0.0080(13) C22 0.0306(15) 0.0343(15) 0.0312(16) -0.0064(13) 0.0020(13) -0.0041(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 2.038(2) . ? Cu1 N4 2.054(2) . ? Cu1 N3 2.059(3) . ? Cu1 N2 2.062(2) . ? Cu1 O1 2.0977(18) . ? Cu2 O4 1.9157(19) 2 ? Cu2 O2 1.972(2) . ? Cu2 O1W 1.978(2) . ? Cu2 O5 1.981(2) 2 ? Cu2 O1 2.2214(18) . ? Cl1 O7 1.408(3) . ? Cl1 O8 1.430(2) . ? Cl1 O9 1.429(3) . ? Cl1 O10 1.432(3) . ? Cl2 O13 1.334(5) . ? Cl2 O14 1.357(4) . ? Cl2 O11 1.359(4) . ? Cl2 O12 1.423(3) . ? O6 C16 1.345(3) . ? O6 C12 1.373(3) . ? O4 C13 1.321(3) . ? O4 Cu2 1.9157(19) 2 ? O5 C14 1.286(3) . ? O5 Cu2 1.981(2) 2 ? O3 C22 1.324(3) . ? O3 C18 1.362(3) . ? O1 C19 1.311(3) . ? O2 C20 1.276(3) . ? N4 C11 1.492(3) . ? N4 C7 1.498(4) . ? N4 C6 1.504(4) . ? N1 C9 1.484(4) . ? N1 C1 1.489(4) . ? N1 C8 1.508(4) . ? N2 C17 1.485(3) . ? N2 C3 1.497(4) . ? N2 C2 1.510(4) . ? N3 C4 1.475(4) . ? N3 C10 1.479(4) . ? N3 C5 1.489(4) . ? C7 C8 1.513(4) . ? C1 C2 1.507(5) . ? C3 C4 1.496(4) . ? C5 C6 1.498(4) . ? C11 C12 1.492(4) . ? C12 C13 1.362(4) . ? C13 C14 1.442(4) . ? C14 C15 1.413(4) . ? C15 C16 1.336(4) . ? C17 C18 1.477(4) . ? C18 C19 1.383(4) . ? C19 C20 1.449(4) . ? C20 C21 1.417(4) . ? C21 C22 1.340(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 N4 86.14(9) . . ? N1 Cu1 N3 150.55(9) . . ? N4 Cu1 N3 86.22(9) . . ? N1 Cu1 N2 86.11(10) . . ? N4 Cu1 N2 149.81(9) . . ? N3 Cu1 N2 86.35(10) . . ? N1 Cu1 O1 102.81(9) . . ? N4 Cu1 O1 117.10(8) . . ? N3 Cu1 O1 106.00(9) . . ? N2 Cu1 O1 93.07(8) . . ? O4 Cu2 O2 170.25(8) 2 . ? O4 Cu2 O1W 91.75(9) 2 . ? O2 Cu2 O1W 88.45(9) . . ? O4 Cu2 O5 84.89(8) 2 2 ? O2 Cu2 O5 92.59(8) . 2 ? O1W Cu2 O5 166.00(9) . 2 ? O4 Cu2 O1 109.69(8) 2 . ? O2 Cu2 O1 79.82(7) . . ? O1W Cu2 O1 100.44(8) . . ? O5 Cu2 O1 93.48(8) 2 . ? O7 Cl1 O8 109.45(19) . . ? O7 Cl1 O9 109.3(2) . . ? O8 Cl1 O9 110.09(16) . . ? O7 Cl1 O10 110.5(3) . . ? O8 Cl1 O10 109.40(19) . . ? O9 Cl1 O10 108.14(17) . . ? O13 Cl2 O14 107.0(5) . . ? O13 Cl2 O11 103.8(4) . . ? O14 Cl2 O11 113.6(3) . . ? O13 Cl2 O12 106.4(4) . . ? O14 Cl2 O12 109.2(3) . . ? O11 Cl2 O12 116.1(3) . . ? C16 O6 C12 119.8(2) . . ? C13 O4 Cu2 110.92(16) . 2 ? C14 O5 Cu2 109.92(17) . 2 ? C22 O3 C18 120.1(2) . . ? C19 O1 Cu1 119.48(16) . . ? C19 O1 Cu2 105.99(16) . . ? Cu1 O1 Cu2 130.16(9) . . ? C20 O2 Cu2 115.28(18) . . ? C11 N4 C7 110.1(2) . . ? C11 N4 C6 112.6(2) . . ? C7 N4 C6 109.6(2) . . ? C11 N4 Cu1 116.52(16) . . ? C7 N4 Cu1 108.23(16) . . ? C6 N4 Cu1 99.31(16) . . ? C9 N1 C1 110.9(2) . . ? C9 N1 C8 112.2(2) . . ? C1 N1 C8 109.2(2) . . ? C9 N1 Cu1 112.85(18) . . ? C1 N1 Cu1 108.75(19) . . ? C8 N1 Cu1 102.57(17) . . ? C17 N2 C3 111.0(2) . . ? C17 N2 C2 107.7(2) . . ? C3 N2 C2 113.4(2) . . ? C17 N2 Cu1 116.55(17) . . ? C3 N2 Cu1 106.98(17) . . ? C2 N2 Cu1 100.93(17) . . ? C4 N3 C10 111.3(2) . . ? C4 N3 C5 110.4(2) . . ? C10 N3 C5 110.1(2) . . ? C4 N3 Cu1 101.53(19) . . ? C10 N3 Cu1 116.14(18) . . ? C5 N3 Cu1 107.01(18) . . ? N4 C7 C8 109.9(2) . . ? N1 C8 C7 109.4(2) . . ? N1 C1 C2 109.9(3) . . ? C1 C2 N2 109.8(2) . . ? N2 C3 C4 109.9(2) . . ? N3 C4 C3 111.0(2) . . ? N3 C5 C6 109.8(2) . . ? C5 C6 N4 109.4(2) . . ? N4 C11 C12 114.1(2) . . ? C13 C12 O6 121.3(2) . . ? C13 C12 C11 127.5(3) . . ? O6 C12 C11 111.2(2) . . ? O4 C13 C12 124.7(2) . . ? O4 C13 C14 116.9(2) . . ? C12 C13 C14 118.4(3) . . ? O5 C14 C15 124.7(3) . . ? O5 C14 C13 117.3(3) . . ? C15 C14 C13 118.0(3) . . ? C16 C15 C14 119.5(3) . . ? C15 C16 O6 122.8(3) . . ? C18 C17 N2 112.0(2) . . ? O3 C18 C19 122.0(3) . . ? O3 C18 C17 112.6(2) . . ? C19 C18 C17 125.2(3) . . ? O1 C19 C18 124.3(3) . . ? O1 C19 C20 118.6(2) . . ? C18 C19 C20 117.1(2) . . ? O2 C20 C21 123.3(3) . . ? O2 C20 C19 119.1(2) . . ? C21 C20 C19 117.7(2) . . ? C22 C21 C20 119.8(3) . . ? O3 C22 C21 123.1(3) . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.043 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.085