# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Sergiu Shova' _publ_contact_author_email shova@usm.md loop_ _publ_author_name A.Lazarescu S.Shova J.Bartolome P.Alonso A.Arauzo A.Balu ; Yu.Simonov ; M.Gdaniec C.Turta R.Luque data_shelxl _database_code_depnum_ccdc_archive 'CCDC 774555' #TrackingRef '774555.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Ca N2 O11' _chemical_formula_weight 426.35 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' Ca Ca 0.2262 0.3064 '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 6.6149(13) _cell_length_b 30.137(6) _cell_length_c 8.2217(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.14(3) _cell_angle_gamma 90.00 _cell_volume 1639.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.453 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8396 _exptl_absorpt_correction_T_max 0.9561 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 'Oxford Difraction, XCALIBUR' _diffrn_measurement_method omega-phi _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10559 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3404 _reflns_number_gt 3181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material '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. 24 restrains were applied in order to avoid non-positive definite for anisotropic displacements parameters for four atoms. ; _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^)+(0.0000P)^2^+38.9592P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3404 _refine_ls_number_parameters 254 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.2254 _refine_ls_wR_factor_gt 0.2235 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.012 _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 C12 C 0.8278(12) 0.2965(3) 0.4761(10) 0.0101(15) Uani 1 1 d . . . C13 C 0.8986(13) 0.2539(3) 0.5198(14) 0.023(2) Uani 1 1 d . . . C14 C 1.0852(14) 0.2522(3) 0.6031(11) 0.0191(18) Uani 1 1 d . . . H14 H 1.1339 0.2249 0.6389 0.023 Uiso 1 1 calc R . . C15 C 1.1959(14) 0.2896(3) 0.6324(12) 0.023(2) Uani 1 1 d . . . H15 H 1.3191 0.2882 0.6868 0.027 Uiso 1 1 calc R . . C16 C 1.1185(13) 0.3298(3) 0.5782(11) 0.0151(17) Uani 1 1 d . . . H16 H 1.1957 0.3553 0.5939 0.018 Uiso 1 1 calc R . . C17 C 0.6219(14) 0.3080(3) 0.4032(11) 0.0146(17) Uani 1 1 d . . . C18 C 0.8020(12) 0.2091(3) 0.4857(11) 0.0163(17) Uani 1 1 d . . . C22 C 1.2486(14) 0.4658(2) 0.1246(8) 0.0082(13) Uani 1 1 d U . . C23 C 1.2600(14) 0.4296(2) 0.2277(8) 0.0093(13) Uani 1 1 d U . . C24 C 1.2668(14) 0.3868(2) 0.1615(11) 0.0174(17) Uani 1 1 d . . . H24 H 1.2711 0.3622 0.2299 0.021 Uiso 1 1 calc R . . C25 C 1.2670(13) 0.3809(2) -0.0054(10) 0.0178(15) Uani 1 1 d U . . H25 H 1.2714 0.3525 -0.0494 0.021 Uiso 1 1 calc R . . C26 C 1.2604(18) 0.4178(3) -0.1071(11) 0.0241(18) Uani 1 1 d . . . H26 H 1.2626 0.4146 -0.2195 0.029 Uiso 1 1 calc R . . C27 C 1.2395(14) 0.5141(2) 0.1743(9) 0.0121(14) Uani 1 1 d . . . C28 C 1.2582(14) 0.4351(2) 0.4124(9) 0.0101(14) Uani 1 1 d . . . N11 N 0.9359(10) 0.3340(2) 0.5035(9) 0.0117(13) Uani 1 1 d . . . N21 N 1.2510(13) 0.4580(2) -0.0388(7) 0.0165(14) Uani 1 1 d . . . H21 H 1.2462 0.4806 -0.1026 0.020 Uiso 1 1 calc R . . O1W O 0.6898(10) 0.3840(2) 0.7502(7) 0.0223(15) Uani 1 1 d . . . H2O1 H 0.6858 0.4031 0.8343 0.027 Uiso 1 1 d R . . H1O1 H 0.7593 0.3599 0.7838 0.027 Uiso 1 1 d R . . O2W O 0.7724(10) 0.48929(17) 0.3262(7) 0.0146(11) Uani 1 1 d U . . H1O2 H 0.8954 0.4984 0.3255 0.017 Uiso 1 1 d R . . H2O2 H 0.7135 0.5092 0.3840 0.017 Uiso 1 1 d R . . O3W O 0.7700(11) 0.40188(18) 0.2015(6) 0.0176(13) Uani 1 1 d . . . H1O3 H 0.7783 0.4237 0.1271 0.021 Uiso 1 1 d R . . H2O3 H 0.8098 0.3767 0.1522 0.021 Uiso 1 1 d R . . O11 O 0.5566(9) 0.3454(2) 0.4200(7) 0.0147(12) Uani 1 1 d . . . O12 O 0.5264(10) 0.2777(2) 0.3221(9) 0.0247(15) Uani 1 1 d . . . H12 H 0.5305 0.2495 0.3198 0.030 Uiso 1 1 d R . . O13 O 0.8698(12) 0.1767(2) 0.5650(10) 0.0317(18) Uani 1 1 d . . . O14 O 0.6644(11) 0.2057(2) 0.3778(8) 0.0259(16) Uani 1 1 d . . . O21 O 1.2066(9) 0.52197(19) 0.3233(7) 0.0137(13) Uani 1 1 d . . . O22 O 1.2668(17) 0.54128(19) 0.0627(7) 0.037(2) Uani 1 1 d . . . O23 O 1.4279(8) 0.44269(19) 0.4790(8) 0.0124(12) Uani 1 1 d . . . O24 O 1.0974(8) 0.42987(19) 0.4856(8) 0.0152(12) Uani 1 1 d . . . Ca1 Ca 0.7548(3) 0.41249(4) 0.48454(17) 0.0088(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 C12 0.010(3) 0.018(4) 0.002(3) -0.002(3) 0.002(3) 0.001(3) C13 0.021(4) 0.015(4) 0.033(6) 0.003(4) 0.000(4) 0.002(3) C14 0.023(4) 0.020(4) 0.015(4) 0.000(3) -0.011(4) 0.007(4) C15 0.019(5) 0.023(4) 0.026(5) 0.002(4) -0.011(4) 0.003(3) C16 0.011(4) 0.022(4) 0.013(4) -0.006(3) -0.004(3) -0.001(3) C17 0.017(4) 0.021(4) 0.006(4) 0.000(3) -0.005(3) -0.009(3) C18 0.020(4) 0.021(4) 0.008(4) -0.003(3) 0.009(4) 0.003(3) C22 0.0082(15) 0.0086(15) 0.0076(15) 0.0000(9) 0.0001(10) 0.0002(10) C23 0.0091(16) 0.0098(15) 0.0090(16) -0.0001(10) -0.0002(10) 0.0000(10) C24 0.015(4) 0.012(3) 0.025(4) 0.002(3) 0.007(5) 0.005(3) C25 0.0183(18) 0.0179(17) 0.0172(18) -0.0007(10) 0.0010(10) -0.0003(10) C26 0.031(5) 0.020(4) 0.022(4) -0.004(3) -0.006(5) -0.003(5) C27 0.013(3) 0.015(3) 0.008(3) 0.000(3) 0.000(4) -0.002(4) C28 0.011(3) 0.006(3) 0.013(3) 0.005(2) 0.004(4) 0.002(3) N11 0.010(3) 0.021(3) 0.004(3) -0.005(3) 0.001(3) -0.001(2) N21 0.024(3) 0.018(3) 0.007(3) 0.001(2) 0.003(4) 0.000(3) O1W 0.042(4) 0.018(3) 0.007(3) -0.001(2) 0.003(3) 0.001(3) O2W 0.0145(14) 0.0151(14) 0.0141(14) -0.0004(9) 0.0012(10) 0.0003(10) O3W 0.030(4) 0.018(3) 0.004(2) -0.0024(19) -0.002(3) 0.002(3) O11 0.013(3) 0.023(3) 0.008(3) 0.000(2) -0.002(3) -0.005(2) O12 0.026(4) 0.022(3) 0.026(4) -0.003(3) -0.014(3) -0.006(3) O13 0.035(4) 0.018(3) 0.042(5) 0.012(3) 0.012(4) 0.001(3) O14 0.036(4) 0.019(3) 0.023(4) -0.003(3) 0.002(3) -0.007(3) O21 0.019(3) 0.020(3) 0.003(2) -0.001(2) 0.000(2) -0.003(2) O22 0.087(6) 0.016(3) 0.008(3) 0.001(2) 0.007(4) -0.006(4) O23 0.006(2) 0.024(3) 0.007(3) -0.003(2) -0.001(2) 0.003(2) O24 0.009(2) 0.024(3) 0.012(3) 0.002(3) 0.004(3) -0.001(2) Ca1 0.0063(6) 0.0135(6) 0.0065(6) 0.0002(5) 0.0011(9) -0.0002(6) _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 C12 N11 1.355(10) . ? C12 C13 1.413(11) . ? C12 C17 1.526(12) . ? C13 C14 1.411(12) . ? C13 C18 1.519(12) . ? C14 C15 1.365(13) . ? C15 C16 1.390(12) . ? C16 N11 1.360(11) . ? C17 O11 1.215(11) . ? C17 O12 1.295(10) . ? C18 O13 1.256(11) . ? C18 O14 1.274(11) . ? C22 N21 1.364(9) . ? C22 C23 1.383(9) . ? C22 C27 1.514(9) . ? C23 C24 1.400(10) . ? C23 C28 1.528(10) . ? C24 C25 1.383(12) . ? C25 C26 1.393(11) . ? C26 N21 1.335(10) . ? C27 O22 1.244(9) . ? C27 O21 1.267(9) . ? C28 O24 1.233(11) . ? C28 O23 1.269(11) . ? N11 Ca1 2.656(7) . ? O1W Ca1 2.388(6) . ? O2W Ca1 2.658(5) . ? O3W Ca1 2.351(5) . ? O11 Ca1 2.467(6) . ? O21 Ca1 2.542(6) 3_766 ? O23 Ca1 2.346(6) 1_655 ? O24 Ca1 2.326(6) . ? Ca1 O23 2.346(6) 1_455 ? Ca1 O21 2.542(6) 3_766 ? 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 N11 C12 C13 122.7(8) . . ? N11 C12 C17 110.2(7) . . ? C13 C12 C17 126.9(7) . . ? C14 C13 C12 116.5(8) . . ? C14 C13 C18 115.1(7) . . ? C12 C13 C18 128.4(8) . . ? C15 C14 C13 121.6(8) . . ? C14 C15 C16 117.9(8) . . ? N11 C16 C15 123.4(8) . . ? O11 C17 O12 122.7(8) . . ? O11 C17 C12 118.9(7) . . ? O12 C17 C12 118.4(8) . . ? O13 C18 O14 123.5(8) . . ? O13 C18 C13 116.4(8) . . ? O14 C18 C13 120.0(8) . . ? N21 C22 C23 117.8(6) . . ? N21 C22 C27 115.6(6) . . ? C23 C22 C27 126.6(6) . . ? C22 C23 C24 119.3(7) . . ? C22 C23 C28 121.5(6) . . ? C24 C23 C28 119.2(6) . . ? C25 C24 C23 120.2(7) . . ? C24 C25 C26 119.5(7) . . ? N21 C26 C25 118.3(8) . . ? O22 C27 O21 128.0(7) . . ? O22 C27 C22 115.4(6) . . ? O21 C27 C22 116.6(6) . . ? O24 C28 O23 125.1(7) . . ? O24 C28 C23 118.7(8) . . ? O23 C28 C23 116.0(8) . . ? C12 N11 C16 117.8(7) . . ? C12 N11 Ca1 119.7(5) . . ? C16 N11 Ca1 120.6(5) . . ? C26 N21 C22 124.8(7) . . ? C17 O11 Ca1 126.6(5) . . ? C27 O21 Ca1 136.8(5) . 3_766 ? C28 O23 Ca1 138.9(5) . 1_655 ? C28 O24 Ca1 150.2(6) . . ? O24 Ca1 O23 144.1(2) . 1_455 ? O24 Ca1 O3W 89.5(2) . . ? O23 Ca1 O3W 94.3(2) 1_455 . ? O24 Ca1 O1W 104.8(2) . . ? O23 Ca1 O1W 89.4(2) 1_455 . ? O3W Ca1 O1W 149.9(2) . . ? O24 Ca1 O11 134.6(2) . . ? O23 Ca1 O11 79.9(2) 1_455 . ? O3W Ca1 O11 72.5(2) . . ? O1W Ca1 O11 78.8(2) . . ? O24 Ca1 O21 74.1(2) . 3_766 ? O23 Ca1 O21 78.6(2) 1_455 3_766 ? O3W Ca1 O21 135.76(19) . 3_766 ? O1W Ca1 O21 74.3(2) . 3_766 ? O11 Ca1 O21 145.4(2) . 3_766 ? O24 Ca1 N11 76.2(2) . . ? O23 Ca1 N11 139.6(2) 1_455 . ? O3W Ca1 N11 85.2(2) . . ? O1W Ca1 N11 73.0(2) . . ? O11 Ca1 N11 61.4(2) . . ? O21 Ca1 N11 127.7(2) 3_766 . ? O24 Ca1 O2W 76.2(2) . . ? O23 Ca1 O2W 72.2(2) 1_455 . ? O3W Ca1 O2W 68.39(18) . . ? O1W Ca1 O2W 140.3(2) . . ? O11 Ca1 O2W 129.2(2) . . ? O21 Ca1 O2W 67.88(17) 3_766 . ? N11 Ca1 O2W 141.6(2) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.727 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.162 # Attachment '774556.cif' data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 774556' #TrackingRef '774556.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 Ba Co N2 O16' _chemical_formula_weight 670.61 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' Ba Ba -0.3244 2.2819 '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 8.8466(3) _cell_length_b 11.3244(5) _cell_length_c 11.4821(4) _cell_angle_alpha 102.232(3) _cell_angle_beta 91.490(3) _cell_angle_gamma 106.382(3) _cell_volume 1074.03(7) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.074 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 662 _exptl_absorpt_coefficient_mu 2.680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5002 _exptl_absorpt_correction_T_max 0.7754 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _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 'Oxford Difraction, XCALIBUR' _diffrn_measurement_method omega-phi _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13924 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4187 _reflns_number_gt 3867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material '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^)+(0.0247P)^2^+0.2695P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4187 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0200 _refine_ls_R_factor_gt 0.0171 _refine_ls_wR_factor_ref 0.0418 _refine_ls_wR_factor_gt 0.0409 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2027(2) 0.54579(19) 0.89155(17) 0.0089(4) Uani 1 1 d . . . C2 C 0.0925(2) 0.62013(18) 0.94364(17) 0.0082(4) Uani 1 1 d . . . C3 C -0.0449(2) 0.61872(19) 0.88066(17) 0.0089(4) Uani 1 1 d . . . C4 C -0.1046(2) 0.53931(19) 0.75487(17) 0.0090(4) Uani 1 1 d . . . C5 C -0.1383(2) 0.6885(2) 0.94020(18) 0.0125(4) Uani 1 1 d . . . H5 H -0.2308 0.6900 0.9010 0.015 Uiso 1 1 calc R . . C6 C -0.0937(3) 0.7558(2) 1.05783(18) 0.0130(4) Uani 1 1 d . . . H6 H -0.1549 0.8031 1.0980 0.016 Uiso 1 1 calc R . . C7 C 0.0440(2) 0.75071(19) 1.11398(18) 0.0106(4) Uani 1 1 d . . . H8 H 0.0737 0.7945 1.1932 0.013 Uiso 1 1 calc R . . C8 C 0.4822(2) 0.9152(2) 1.28383(18) 0.0111(4) Uani 1 1 d . . . C9 C 0.5611(2) 0.92462(19) 1.17042(17) 0.0095(4) Uani 1 1 d . . . C10 C 0.6794(2) 1.03176(19) 1.15996(18) 0.0105(4) Uani 1 1 d . . . C11 C 0.7482(2) 1.1457(2) 1.26359(18) 0.0118(4) Uani 1 1 d . . . C12 C 0.7384(2) 1.0322(2) 1.04818(18) 0.0134(4) Uani 1 1 d . . . H12 H 0.8194 1.1011 1.0378 0.016 Uiso 1 1 calc R . . C13 C 0.6760(3) 0.9300(2) 0.95330(19) 0.0144(5) Uani 1 1 d . . . H13 H 0.7124 0.9304 0.8781 0.017 Uiso 1 1 calc R . . C14 C 0.5581(2) 0.8265(2) 0.97148(18) 0.0114(4) Uani 1 1 d . . . H15 H 0.5158 0.7580 0.9073 0.014 Uiso 1 1 calc R . . N1 N 0.1358(2) 0.68512(16) 1.05831(14) 0.0093(4) Uani 1 1 d . . . N2 N 0.5037(2) 0.82265(16) 1.07876(14) 0.0096(4) Uani 1 1 d . . . O1 O 0.31871(16) 0.55027(13) 0.96321(12) 0.0112(3) Uani 1 1 d . . . O2 O 0.17474(17) 0.48523(13) 0.78646(12) 0.0115(3) Uani 1 1 d . . . O1W O 0.52234(18) 0.58979(15) 1.17894(13) 0.0171(3) Uani 1 1 d . . . H1O1 H 0.5667 0.5447 1.1245 0.020 Uiso 1 1 d R . . H2O1 H 0.5912 0.6223 1.2440 0.020 Uiso 1 1 d R . . O3 O -0.05583(17) 0.58221(13) 0.66716(12) 0.0121(3) Uani 1 1 d . . . O2W O 0.43312(17) 0.74213(13) 0.49574(12) 0.0128(3) Uani 1 1 d . . . H1O2 H 0.4079 0.7608 0.4283 0.015 Uiso 1 1 d R . . H2O2 H 0.4439 0.8088 0.5555 0.015 Uiso 1 1 d R . . O4 O -0.21037(17) 0.43582(14) 0.74860(12) 0.0134(3) Uani 1 1 d . . . O3W O 0.43292(17) 0.43263(14) 0.36726(13) 0.0168(3) Uani 1 1 d . . . H1O3 H 0.4229 0.4790 0.3153 0.020 Uiso 1 1 d R . . H2O3 H 0.3732 0.3529 0.3353 0.020 Uiso 1 1 d R . . O5 O 0.38526(17) 0.80754(13) 1.28476(12) 0.0127(3) Uani 1 1 d . . . O4W O 0.30705(17) 0.31177(14) 0.60302(13) 0.0141(3) Uani 1 1 d . . . H1O4 H 0.3800 0.2857 0.5604 0.017 Uiso 1 1 d R . . H2O4 H 0.2369 0.2439 0.6173 0.017 Uiso 1 1 d R . . O6 O 0.50958(19) 1.00930(14) 1.36738(13) 0.0188(4) Uani 1 1 d . . . O5W O 0.05379(17) 0.67278(14) 0.46491(13) 0.0145(3) Uani 1 1 d . . . H1O5 H 0.1125 0.6952 0.4061 0.017 Uiso 1 1 d R . . H2O5 H 0.0771 0.7424 0.5260 0.017 Uiso 1 1 d R . . O7 O 0.70150(17) 1.23977(13) 1.26763(13) 0.0143(3) Uani 1 1 d . . . O6W O 0.1087(2) 0.09058(15) 0.65534(15) 0.0248(4) Uani 1 1 d . . . H1O6 H 0.0078 0.0760 0.6283 0.030 Uiso 1 1 d R . . H2O6 H 0.1193 0.0287 0.6894 0.030 Uiso 1 1 d R . . O8 O 0.85395(18) 1.13497(14) 1.33387(13) 0.0173(3) Uani 1 1 d . . . O7W O 0.2089(2) 0.00808(16) 0.42696(15) 0.0273(4) Uani 1 1 d . . . H1O7 H 0.3004 -0.0122 0.4189 0.033 Uiso 1 1 d R . . H2O7 H 0.1986 0.0257 0.5056 0.033 Uiso 1 1 d R . . O8W O 0.20435(18) 0.20143(15) 0.30560(14) 0.0202(4) Uani 1 1 d . . . H1O8 H 0.1094 0.2124 0.3100 0.024 Uiso 1 1 d R . . H2O8 H 0.2126 0.1456 0.3471 0.024 Uiso 1 1 d R . . Co Co 0.34275(3) 0.66260(3) 1.13334(2) 0.00781(7) Uani 1 1 d . . . Ba Ba 0.233162(14) 0.530161(11) 0.564695(10) 0.00849(4) 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 C1 0.0099(10) 0.0060(10) 0.0101(10) 0.0032(8) 0.0019(8) 0.0000(8) C2 0.0100(10) 0.0041(10) 0.0091(9) 0.0017(8) 0.0023(8) -0.0004(8) C3 0.0094(10) 0.0060(10) 0.0105(10) 0.0029(8) 0.0018(8) 0.0003(8) C4 0.0080(10) 0.0101(11) 0.0100(10) 0.0010(8) 0.0006(8) 0.0053(8) C5 0.0113(10) 0.0133(11) 0.0133(10) 0.0024(8) -0.0002(8) 0.0049(9) C6 0.0147(11) 0.0128(11) 0.0129(10) 0.0018(8) 0.0044(8) 0.0070(9) C7 0.0131(10) 0.0089(11) 0.0075(9) -0.0006(8) 0.0014(8) 0.0016(8) C8 0.0129(10) 0.0101(11) 0.0112(10) 0.0018(8) 0.0002(8) 0.0053(9) C9 0.0111(10) 0.0082(10) 0.0098(10) 0.0006(8) -0.0006(8) 0.0051(8) C10 0.0114(10) 0.0098(11) 0.0123(10) 0.0031(8) 0.0009(8) 0.0059(8) C11 0.0121(10) 0.0093(11) 0.0116(10) 0.0019(8) 0.0050(8) -0.0006(9) C12 0.0137(11) 0.0108(11) 0.0168(11) 0.0051(9) 0.0054(8) 0.0037(9) C13 0.0182(11) 0.0170(12) 0.0108(10) 0.0044(9) 0.0057(8) 0.0082(9) C14 0.0126(10) 0.0140(11) 0.0084(10) -0.0004(8) 0.0005(8) 0.0073(9) N1 0.0108(8) 0.0073(9) 0.0085(8) 0.0018(7) 0.0008(7) 0.0008(7) N2 0.0093(8) 0.0096(9) 0.0096(8) 0.0005(7) -0.0005(7) 0.0038(7) O1 0.0107(7) 0.0121(8) 0.0101(7) -0.0004(6) -0.0017(6) 0.0048(6) O2 0.0139(7) 0.0119(7) 0.0081(7) 0.0001(6) 0.0004(6) 0.0046(6) O1W 0.0180(8) 0.0236(9) 0.0108(7) -0.0040(6) -0.0046(6) 0.0144(7) O3 0.0130(7) 0.0131(8) 0.0093(7) 0.0034(6) -0.0001(6) 0.0021(6) O2W 0.0177(8) 0.0107(8) 0.0090(7) 0.0007(6) 0.0021(6) 0.0038(6) O4 0.0144(8) 0.0114(8) 0.0098(7) 0.0014(6) -0.0006(6) -0.0026(6) O3W 0.0160(8) 0.0140(8) 0.0189(8) 0.0063(6) -0.0046(6) 0.0006(6) O5 0.0147(7) 0.0092(8) 0.0105(7) 0.0008(6) 0.0024(6) -0.0013(6) O4W 0.0133(7) 0.0128(8) 0.0159(7) 0.0010(6) 0.0037(6) 0.0048(6) O6 0.0274(9) 0.0101(8) 0.0118(7) -0.0029(6) 0.0054(6) -0.0020(7) O5W 0.0142(8) 0.0138(8) 0.0129(7) 0.0017(6) 0.0015(6) 0.0010(6) O7 0.0168(8) 0.0083(8) 0.0169(8) 0.0009(6) 0.0025(6) 0.0035(6) O6W 0.0248(9) 0.0191(9) 0.0296(9) 0.0091(7) 0.0001(7) 0.0027(7) O8 0.0179(8) 0.0117(8) 0.0191(8) 0.0011(6) -0.0047(6) 0.0016(7) O7W 0.0224(9) 0.0308(10) 0.0286(9) 0.0037(8) 0.0088(7) 0.0094(8) O8W 0.0171(8) 0.0224(9) 0.0219(8) 0.0059(7) 0.0036(7) 0.0062(7) Co 0.00836(14) 0.00746(14) 0.00649(13) -0.00008(11) -0.00048(10) 0.00190(11) Ba 0.00814(7) 0.00842(7) 0.00819(6) 0.00100(4) -0.00011(4) 0.00205(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.235(2) . ? C1 O1 1.281(2) . ? C1 C2 1.515(3) . ? C2 N1 1.351(3) . ? C2 C3 1.393(3) . ? C3 C5 1.394(3) . ? C3 C4 1.522(3) . ? C4 O3 1.244(2) . ? C4 O4 1.263(2) . ? C5 C6 1.388(3) . ? C6 C7 1.385(3) . ? C7 N1 1.336(3) . ? C8 O6 1.235(2) . ? C8 O5 1.279(2) . ? C8 C9 1.503(3) . ? C9 N2 1.351(3) . ? C9 C10 1.391(3) . ? C10 C12 1.398(3) . ? C10 C11 1.523(3) . ? C11 O7 1.240(3) . ? C11 O8 1.268(3) . ? C12 C13 1.380(3) . ? C13 C14 1.389(3) . ? C14 N2 1.339(3) . ? N1 Co 2.1053(17) . ? N2 Co 2.1858(17) . ? O1 Co 2.0621(14) . ? O2 Ba 2.7348(14) . ? O1W Co 2.0872(15) . ? O3 Ba 2.8963(14) 2_566 ? O3 Ba 2.9967(14) . ? O2W Ba 2.8286(14) . ? O4 Co 2.1066(14) 2_567 ? O3W Ba 2.9245(15) 2_666 ? O3W Ba 3.1193(16) . ? O5 Co 2.0656(14) . ? O4W Ba 2.8453(15) . ? O5W Ba 2.8592(14) 2_566 ? O5W Ba 2.9283(15) . ? O7 Ba 2.7921(14) 2_677 ? Co O4 2.1066(14) 2_567 ? Ba O7 2.7921(14) 2_677 ? Ba O5W 2.8591(14) 2_566 ? Ba O3 2.8963(14) 2_566 ? Ba O3W 2.9246(15) 2_666 ? Ba Ba 4.1658(3) 2_566 ? 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 O2 C1 O1 125.07(19) . . ? O2 C1 C2 119.18(18) . . ? O1 C1 C2 115.75(17) . . ? N1 C2 C3 122.43(19) . . ? N1 C2 C1 114.35(17) . . ? C3 C2 C1 123.18(18) . . ? C2 C3 C5 117.42(18) . . ? C2 C3 C4 124.21(18) . . ? C5 C3 C4 118.24(18) . . ? O3 C4 O4 124.76(18) . . ? O3 C4 C3 119.44(17) . . ? O4 C4 C3 115.63(17) . . ? C6 C5 C3 120.3(2) . . ? C7 C6 C5 118.4(2) . . ? N1 C7 C6 122.29(18) . . ? O6 C8 O5 124.26(19) . . ? O6 C8 C9 119.70(19) . . ? O5 C8 C9 116.00(17) . . ? N2 C9 C10 123.00(18) . . ? N2 C9 C8 114.50(17) . . ? C10 C9 C8 122.46(18) . . ? C9 C10 C12 117.32(19) . . ? C9 C10 C11 123.42(18) . . ? C12 C10 C11 119.26(18) . . ? O7 C11 O8 127.04(19) . . ? O7 C11 C10 117.68(18) . . ? O8 C11 C10 115.19(18) . . ? C13 C12 C10 119.8(2) . . ? C12 C13 C14 119.21(19) . . ? N2 C14 C13 121.88(19) . . ? C7 N1 C2 119.16(17) . . ? C7 N1 Co 126.68(13) . . ? C2 N1 Co 114.09(13) . . ? C14 N2 C9 118.74(18) . . ? C14 N2 Co 128.09(14) . . ? C9 N2 Co 112.95(13) . . ? C1 O1 Co 117.48(13) . . ? C1 O2 Ba 137.52(13) . . ? C4 O3 Ba 118.99(12) . 2_566 ? C4 O3 Ba 118.85(12) . . ? Ba O3 Ba 89.95(4) 2_566 . ? C4 O4 Co 137.86(13) . 2_567 ? Ba O3W Ba 117.54(5) 2_666 . ? C8 O5 Co 119.32(13) . . ? Ba O5W Ba 92.07(4) 2_566 . ? C11 O7 Ba 132.02(13) . 2_677 ? O1 Co O5 167.23(6) . . ? O1 Co O1W 88.77(6) . . ? O5 Co O1W 95.98(6) . . ? O1 Co N1 78.28(6) . . ? O5 Co N1 98.60(6) . . ? O1W Co N1 164.17(6) . . ? O1 Co O4 111.84(6) . 2_567 ? O5 Co O4 80.39(5) . 2_567 ? O1W Co O4 85.88(6) . 2_567 ? N1 Co O4 90.49(6) . 2_567 ? O1 Co N2 91.46(6) . . ? O5 Co N2 76.40(6) . . ? O1W Co N2 94.34(6) . . ? N1 Co N2 95.04(6) . . ? O4 Co N2 156.69(6) 2_567 . ? O2 Ba O7 70.65(4) . 2_677 ? O2 Ba O2W 130.81(4) . . ? O7 Ba O2W 64.16(4) 2_677 . ? O2 Ba O4W 66.37(4) . . ? O7 Ba O4W 125.11(4) 2_677 . ? O2W Ba O4W 128.25(4) . . ? O2 Ba O5W 73.02(4) . 2_566 ? O7 Ba O5W 125.29(4) 2_677 2_566 ? O2W Ba O5W 151.72(4) . 2_566 ? O4W Ba O5W 71.37(4) . 2_566 ? O2 Ba O3 131.65(4) . 2_566 ? O7 Ba O3 136.65(4) 2_677 2_566 ? O2W Ba O3 95.56(4) . 2_566 ? O4W Ba O3 97.83(4) . 2_566 ? O5W Ba O3 58.67(4) 2_566 2_566 ? O2 Ba O3W 87.09(4) . 2_666 ? O7 Ba O3W 80.79(4) 2_677 2_666 ? O2W Ba O3W 67.94(4) . 2_666 ? O4W Ba O3W 64.83(4) . 2_666 ? O5W Ba O3W 136.13(4) 2_566 2_666 ? O3 Ba O3W 128.90(4) 2_566 2_666 ? O2 Ba O5W 118.46(4) . . ? O7 Ba O5W 75.42(4) 2_677 . ? O2W Ba O5W 67.88(4) . . ? O4W Ba O5W 156.73(4) . . ? O5W Ba O5W 87.93(4) 2_566 . ? O3 Ba O5W 61.28(4) 2_566 . ? O3W Ba O5W 135.46(4) 2_666 . ? O2 Ba O3 62.92(4) . . ? O7 Ba O3 66.58(4) 2_677 . ? O2W Ba O3 112.24(4) . . ? O4W Ba O3 117.46(4) . . ? O5W Ba O3 60.87(4) 2_566 . ? O3 Ba O3 90.05(4) 2_566 . ? O3W Ba O3 141.02(4) 2_666 . ? O5W Ba O3 56.82(4) . . ? O2 Ba O3W 133.08(4) . . ? O7 Ba O3W 130.81(4) 2_677 . ? O2W Ba O3W 71.96(4) . . ? O4W Ba O3W 68.46(4) . . ? O5W Ba O3W 103.88(4) 2_566 . ? O3 Ba O3W 66.45(4) 2_566 . ? O3W Ba O3W 62.46(5) 2_666 . ? O5W Ba O3W 108.00(4) . . ? O3 Ba O3W 156.50(4) . . ? O2 Ba Ba 97.73(3) . 2_566 ? O7 Ba Ba 102.69(3) 2_677 2_566 ? O2W Ba Ba 109.86(3) . 2_566 ? O4W Ba Ba 115.24(3) . 2_566 ? O5W Ba Ba 44.62(3) 2_566 2_566 ? O3 Ba Ba 46.00(3) 2_566 2_566 ? O3W Ba Ba 174.76(3) 2_666 2_566 ? O5W Ba Ba 43.31(3) . 2_566 ? O3 Ba Ba 44.05(3) . 2_566 ? O3W Ba Ba 112.45(3) . 2_566 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.436 _refine_diff_density_min -0.603 _refine_diff_density_rms 0.074 # Attachment '774557.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 774557' #TrackingRef '774557.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 Ca Co N2 O17' _chemical_formula_weight 591.36 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' Ca Ca 0.2262 0.3064 '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 8.8190(3) _cell_length_b 11.4750(3) _cell_length_c 11.7590(5) _cell_angle_alpha 86.2450(10) _cell_angle_beta 72.7850(10) _cell_angle_gamma 89.4840(10) _cell_volume 1134.17(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour pink _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 610 _exptl_absorpt_coefficient_mu 1.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6742 _exptl_absorpt_correction_T_max 0.8145 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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 'Oxford Difraction, XCALIBUR' _diffrn_measurement_method omega-phi _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15108 _diffrn_reflns_av_R_equivalents 0.1313 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4447 _reflns_number_gt 2997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material '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^)+(0.0802P)^2^+3.7911P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4447 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.1999 _refine_ls_wR_factor_gt 0.1773 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.0481(7) 0.2354(5) 0.8684(5) 0.0188(13) Uani 1 1 d . . . C2 C -0.0460(7) 0.3462(5) 0.8932(5) 0.0171(13) Uani 1 1 d . . . C3 C -0.1675(7) 0.3618(5) 0.9980(5) 0.0194(13) Uani 1 1 d . . . C4 C -0.2276(7) 0.2654(5) 1.0966(6) 0.0221(14) Uani 1 1 d . . . C5 C -0.2382(8) 0.4710(6) 1.0114(6) 0.0256(15) Uani 1 1 d . . . H5 H -0.3203 0.4842 1.0799 0.031 Uiso 1 1 calc R . . C6 C -0.1868(8) 0.5597(6) 0.9236(6) 0.0267(15) Uani 1 1 d . . . H6 H -0.2321 0.6333 0.9329 0.032 Uiso 1 1 calc R . . C7 C -0.0671(7) 0.5373(5) 0.8217(6) 0.0197(13) Uani 1 1 d . . . H7 H -0.0315 0.5971 0.7627 0.024 Uiso 1 1 calc R . . C8 C 0.2822(7) 0.6052(5) 0.5651(5) 0.0174(13) Uani 1 1 d . . . C9 C 0.3986(7) 0.5548(5) 0.6255(5) 0.0140(12) Uani 1 1 d . . . C10 C 0.5334(7) 0.6140(5) 0.6313(5) 0.0170(13) Uani 1 1 d . . . C11 C 0.5842(7) 0.7340(5) 0.5717(5) 0.0177(13) Uani 1 1 d . . . C12 C 0.6321(8) 0.5569(5) 0.6891(6) 0.0231(14) Uani 1 1 d . . . H12 H 0.7220 0.5948 0.6949 0.028 Uiso 1 1 calc R . . C13 C 0.5975(7) 0.4447(5) 0.7377(6) 0.0224(14) Uani 1 1 d . . . H13 H 0.6623 0.4065 0.7775 0.027 Uiso 1 1 calc R . . C14 C 0.4637(7) 0.3894(5) 0.7264(5) 0.0189(13) Uani 1 1 d . . . H14 H 0.4412 0.3128 0.7578 0.023 Uiso 1 1 calc R . . N1 N -0.0007(6) 0.4323(4) 0.8054(4) 0.0178(11) Uani 1 1 d . . . N2 N 0.3658(6) 0.4429(4) 0.6716(4) 0.0162(11) Uani 1 1 d . . . O1 O 0.1412(5) 0.2302(3) 0.7644(4) 0.0214(10) Uani 1 1 d . . . O2 O 0.0333(5) 0.1583(4) 0.9501(4) 0.0275(11) Uani 1 1 d . . . O1W O -0.0240(5) 0.3187(4) 0.5804(4) 0.0278(11) Uani 1 1 d . . . H1O1 H -0.0746 0.2669 0.6035 0.033 Uiso 1 1 d R . . H2O1 H -0.0887 0.3744 0.5355 0.033 Uiso 1 1 d R . . O3 O -0.1859(6) 0.2710(4) 1.1875(4) 0.0276(11) Uani 1 1 d . . . O2W O 0.3631(5) 1.0497(4) 0.6828(4) 0.0284(11) Uani 1 1 d . . . H1O2 H 0.4582 1.0744 0.6397 0.034 Uiso 1 1 d R . . H2O2 H 0.2943 1.1081 0.6896 0.034 Uiso 1 1 d R . . O4 O -0.3243(6) 0.1927(4) 1.0806(4) 0.0297(11) Uani 1 1 d . . . O3W O 0.3044(6) 0.9681(4) 0.4597(4) 0.0298(11) Uani 1 1 d . . . H1O3 H 0.2576 0.9450 0.4140 0.036 Uiso 1 1 d R . . H2O3 H 0.3360 1.0390 0.4537 0.036 Uiso 1 1 d R . . O5 O 0.1766(5) 0.5362(4) 0.5547(4) 0.0182(9) Uani 1 1 d . . . O4W O -0.0138(6) 0.8232(4) 0.6321(4) 0.0359(12) Uani 1 1 d . . . H1O4 H -0.0835 0.8145 0.7064 0.043 Uiso 1 1 d R . . H2O4 H -0.0451 0.8851 0.5928 0.043 Uiso 1 1 d R . . O6 O 0.2962(5) 0.7099(3) 0.5275(4) 0.0201(10) Uani 1 1 d . . . O5W O 0.0388(6) 0.9630(4) 0.8113(4) 0.0303(11) Uani 1 1 d . . . H21 H 0.0469 1.0299 0.8533 0.036 Uiso 1 1 d R . . H22 H 0.0138 0.9051 0.8721 0.036 Uiso 1 1 d R . . O7 O 0.5186(5) 0.8236(4) 0.6221(4) 0.0213(10) Uani 1 1 d . . . O6W O -0.1745(6) 0.1203(4) 0.7028(4) 0.0340(12) Uani 1 1 d . . . H1O6 H -0.2782 0.1203 0.7536 0.041 Uiso 1 1 d R . . H2O6 H -0.1243 0.0777 0.7469 0.041 Uiso 1 1 d R . . O8 O 0.6992(5) 0.7396(4) 0.4787(4) 0.0241(10) Uani 1 1 d . . . O7W O -0.6928(6) 0.1575(5) 1.1934(5) 0.0457(14) Uani 1 1 d . . . H1O7 H -0.5899 0.1659 1.1890 0.055 Uiso 1 1 d R . . H2O7 H -0.6973 0.1152 1.1327 0.055 Uiso 1 1 d R . . O8W O 0.3095(6) 0.0470(4) 0.9790(4) 0.0350(12) Uani 1 1 d . . . H1O5 H 0.2455 0.0844 0.9538 0.042 Uiso 1 1 d R . . H2O5 H 0.3006 -0.0176 0.9697 0.042 Uiso 1 1 d R . . O9W O -0.4212(6) 0.1877(4) 0.8806(4) 0.0359(12) Uani 1 1 d . . . H1O9 H -0.3847 0.1914 0.9443 0.043 Uiso 1 1 d R . . H2O9 H -0.5040 0.1370 0.9020 0.043 Uiso 1 1 d R . . Co1 Co 0.16268(10) 0.37237(7) 0.64185(7) 0.0166(3) Uani 1 1 d . . . Ca1 Ca 0.24453(15) 0.87212(10) 0.65359(11) 0.0179(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 C1 0.022(3) 0.024(3) 0.013(3) 0.001(2) -0.009(3) -0.002(3) C2 0.019(3) 0.015(3) 0.017(3) 0.000(2) -0.005(2) 0.000(2) C3 0.018(3) 0.023(3) 0.018(3) 0.000(3) -0.007(3) 0.002(3) C4 0.018(3) 0.022(3) 0.023(3) -0.003(3) 0.000(3) 0.006(3) C5 0.028(4) 0.024(4) 0.023(4) 0.000(3) -0.005(3) 0.004(3) C6 0.034(4) 0.025(4) 0.018(3) -0.002(3) -0.002(3) 0.007(3) C7 0.019(3) 0.021(3) 0.022(3) -0.003(3) -0.011(3) 0.000(3) C8 0.011(3) 0.023(3) 0.018(3) -0.002(3) -0.003(2) 0.000(2) C9 0.016(3) 0.011(3) 0.014(3) -0.005(2) -0.003(2) 0.005(2) C10 0.026(4) 0.017(3) 0.005(3) 0.002(2) -0.001(2) -0.002(3) C11 0.007(3) 0.028(4) 0.020(3) -0.001(3) -0.007(3) -0.001(2) C12 0.024(4) 0.015(3) 0.030(4) -0.001(3) -0.008(3) -0.001(3) C13 0.017(3) 0.023(3) 0.027(4) 0.002(3) -0.007(3) 0.006(3) C14 0.024(3) 0.014(3) 0.017(3) 0.002(2) -0.005(3) 0.006(2) N1 0.016(3) 0.017(3) 0.021(3) 0.003(2) -0.007(2) -0.002(2) N2 0.013(3) 0.020(3) 0.016(3) 0.000(2) -0.004(2) -0.003(2) O1 0.021(2) 0.018(2) 0.018(2) -0.0002(17) 0.0045(18) 0.0008(18) O2 0.032(3) 0.024(2) 0.021(2) 0.0058(19) -0.001(2) 0.008(2) O1W 0.018(2) 0.032(3) 0.038(3) 0.003(2) -0.014(2) -0.0068(19) O3 0.034(3) 0.032(3) 0.016(2) 0.0021(19) -0.007(2) -0.002(2) O2W 0.024(3) 0.019(2) 0.040(3) -0.004(2) -0.004(2) -0.0018(19) O4 0.028(3) 0.026(3) 0.030(3) -0.001(2) -0.003(2) -0.006(2) O3W 0.039(3) 0.029(3) 0.026(3) 0.003(2) -0.015(2) -0.013(2) O5 0.012(2) 0.026(2) 0.018(2) 0.0007(18) -0.0079(17) -0.0031(17) O4W 0.027(3) 0.048(3) 0.031(3) -0.004(2) -0.006(2) 0.001(2) O6 0.024(2) 0.014(2) 0.022(2) 0.0021(18) -0.0070(19) -0.0011(18) O5W 0.035(3) 0.025(3) 0.028(3) -0.009(2) -0.004(2) 0.001(2) O7 0.014(2) 0.019(2) 0.029(2) -0.0082(19) -0.0036(19) 0.0005(18) O6W 0.031(3) 0.032(3) 0.042(3) 0.004(2) -0.017(2) -0.012(2) O8 0.024(3) 0.022(2) 0.021(2) -0.0025(18) 0.002(2) -0.0011(19) O7W 0.027(3) 0.068(4) 0.039(3) -0.016(3) -0.003(2) -0.006(3) O8W 0.039(3) 0.032(3) 0.041(3) -0.008(2) -0.020(2) 0.004(2) O9W 0.035(3) 0.044(3) 0.033(3) 0.009(2) -0.018(2) -0.003(2) Co1 0.0157(5) 0.0159(5) 0.0179(5) -0.0001(3) -0.0045(3) -0.0011(3) Ca1 0.0186(7) 0.0156(7) 0.0176(6) -0.0007(5) -0.0026(5) -0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.241(7) . ? C1 O1 1.260(7) . ? C1 C2 1.508(8) . ? C2 N1 1.354(7) . ? C2 C3 1.394(8) . ? C3 C5 1.391(9) . ? C3 C4 1.526(9) . ? C4 O3 1.235(8) . ? C4 O4 1.260(8) . ? C4 Ca1 3.206(7) 2_567 ? C5 C6 1.379(9) . ? C5 H5 0.9300 . ? C6 C7 1.379(9) . ? C6 H6 0.9300 . ? C7 N1 1.335(8) . ? C7 H7 0.9300 . ? C8 O6 1.248(7) . ? C8 O5 1.265(7) . ? C8 C9 1.504(8) . ? C9 N2 1.359(7) . ? C9 C10 1.395(8) . ? C10 C12 1.391(9) . ? C10 C11 1.512(8) . ? C11 O8 1.250(7) . ? C11 O7 1.269(7) . ? C12 C13 1.372(9) . ? C12 H12 0.9300 . ? C13 C14 1.389(9) . ? C13 H13 0.9300 . ? C14 N2 1.344(8) . ? C14 H14 0.9300 . ? N1 Co1 2.182(5) . ? N2 Co1 2.103(5) . ? O1 Co1 2.076(4) . ? O1W Co1 2.096(4) . ? O1W H1O1 0.7333 . ? O1W H2O1 1.0679 . ? O3 Ca1 2.345(4) 2_567 ? O2W Ca1 2.389(4) . ? O2W H1O2 0.8800 . ? O2W H2O2 0.8914 . ? O3W Ca1 2.378(4) . ? O3W H1O3 0.8257 . ? O3W H2O3 0.8540 . ? O5 Co1 2.068(4) . ? O4W Ca1 2.440(5) . ? O4W H1O4 0.9074 . ? O4W H2O4 0.9064 . ? O6 Ca1 2.412(4) . ? O5W Ca1 2.459(4) . ? O5W H21 0.9536 . ? O5W H22 0.9208 . ? O7 Ca1 2.401(4) . ? O6W H1O6 0.9329 . ? O6W H2O6 0.8967 . ? O8 Co1 2.082(4) 2_666 ? O7W H1O7 0.8998 . ? O7W H2O7 0.8986 . ? O8W H1O5 0.8177 . ? O8W H2O5 0.7646 . ? O9W H1O9 0.9011 . ? O9W H2O9 0.9028 . ? Co1 O8 2.082(4) 2_666 ? Ca1 O3 2.345(4) 2_567 ? Ca1 C4 3.206(7) 2_567 ? 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 O2 C1 O1 124.6(6) . . ? O2 C1 C2 119.3(5) . . ? O1 C1 C2 116.1(5) . . ? N1 C2 C3 121.7(5) . . ? N1 C2 C1 114.4(5) . . ? C3 C2 C1 123.9(5) . . ? C5 C3 C2 117.6(6) . . ? C5 C3 C4 118.9(5) . . ? C2 C3 C4 123.4(5) . . ? O3 C4 O4 126.3(6) . . ? O3 C4 C3 117.0(6) . . ? O4 C4 C3 116.5(6) . . ? O3 C4 Ca1 37.2(3) . 2_567 ? O4 C4 Ca1 89.5(4) . 2_567 ? C3 C4 Ca1 154.0(4) . 2_567 ? C6 C5 C3 120.3(6) . . ? C6 C5 H5 119.9 . . ? C3 C5 H5 119.9 . . ? C5 C6 C7 118.8(6) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? N1 C7 C6 122.0(6) . . ? N1 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? O6 C8 O5 124.4(6) . . ? O6 C8 C9 118.9(5) . . ? O5 C8 C9 116.6(5) . . ? N2 C9 C10 121.5(5) . . ? N2 C9 C8 114.4(5) . . ? C10 C9 C8 124.0(5) . . ? C12 C10 C9 118.2(6) . . ? C12 C10 C11 117.8(5) . . ? C9 C10 C11 123.9(5) . . ? O8 C11 O7 123.1(6) . . ? O8 C11 C10 117.3(5) . . ? O7 C11 C10 119.4(5) . . ? C13 C12 C10 120.3(6) . . ? C13 C12 H12 119.9 . . ? C10 C12 H12 119.9 . . ? C12 C13 C14 118.8(6) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? N2 C14 C13 122.1(6) . . ? N2 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C7 N1 C2 119.5(5) . . ? C7 N1 Co1 127.4(4) . . ? C2 N1 Co1 112.8(4) . . ? C14 N2 C9 119.1(5) . . ? C14 N2 Co1 127.5(4) . . ? C9 N2 Co1 113.4(4) . . ? C1 O1 Co1 119.5(4) . . ? Co1 O1W H1O1 125.7 . . ? Co1 O1W H2O1 125.2 . . ? H1O1 O1W H2O1 105.7 . . ? C4 O3 Ca1 124.2(4) . 2_567 ? Ca1 O2W H1O2 123.6 . . ? Ca1 O2W H2O2 110.4 . . ? H1O2 O2W H2O2 109.8 . . ? Ca1 O3W H1O3 117.5 . . ? Ca1 O3W H2O3 115.8 . . ? H1O3 O3W H2O3 120.6 . . ? C8 O5 Co1 116.8(4) . . ? Ca1 O4W H1O4 107.5 . . ? Ca1 O4W H2O4 107.7 . . ? H1O4 O4W H2O4 107.8 . . ? C8 O6 Ca1 124.4(4) . . ? Ca1 O5W H21 129.0 . . ? Ca1 O5W H22 102.8 . . ? H21 O5W H22 101.7 . . ? C11 O7 Ca1 124.5(4) . . ? H1O6 O6W H2O6 101.8 . . ? C11 O8 Co1 138.8(4) . 2_666 ? H1O7 O7W H2O7 107.6 . . ? H1O5 O8W H2O5 108.7 . . ? H1O9 O9W H2O9 107.1 . . ? O5 Co1 O1 166.50(16) . . ? O5 Co1 O8 107.65(17) . 2_666 ? O1 Co1 O8 84.21(16) . 2_666 ? O5 Co1 O1W 92.95(17) . . ? O1 Co1 O1W 94.51(18) . . ? O8 Co1 O1W 85.14(18) 2_666 . ? O5 Co1 N2 78.42(17) . . ? O1 Co1 N2 95.26(18) . . ? O8 Co1 N2 91.26(18) 2_666 . ? O1W Co1 N2 169.20(19) . . ? O5 Co1 N1 92.28(17) . . ? O1 Co1 N1 76.21(17) . . ? O8 Co1 N1 160.00(18) 2_666 . ? O1W Co1 N1 92.27(18) . . ? N2 Co1 N1 94.53(19) . . ? O3 Ca1 O3W 162.99(16) 2_567 . ? O3 Ca1 O2W 116.88(17) 2_567 . ? O3W Ca1 O2W 78.83(16) . . ? O3 Ca1 O7 86.89(16) 2_567 . ? O3W Ca1 O7 91.05(16) . . ? O2W Ca1 O7 76.13(15) . . ? O3 Ca1 O6 85.31(15) 2_567 . ? O3W Ca1 O6 77.92(15) . . ? O2W Ca1 O6 141.15(16) . . ? O7 Ca1 O6 73.63(14) . . ? O3 Ca1 O4W 85.98(17) 2_567 . ? O3W Ca1 O4W 87.10(17) . . ? O2W Ca1 O4W 133.56(17) . . ? O7 Ca1 O4W 148.82(16) . . ? O6 Ca1 O4W 75.55(16) . . ? O3 Ca1 O5W 76.43(16) 2_567 . ? O3W Ca1 O5W 115.94(17) . . ? O2W Ca1 O5W 75.18(16) . . ? O7 Ca1 O5W 135.18(16) . . ? O6 Ca1 O5W 143.46(16) . . ? O4W Ca1 O5W 71.88(16) . . ? O3 Ca1 C4 18.57(16) 2_567 2_567 ? O3W Ca1 C4 170.21(17) . 2_567 ? O2W Ca1 C4 98.48(17) . 2_567 ? O7 Ca1 C4 79.17(16) . 2_567 ? O6 Ca1 C4 99.19(15) . 2_567 ? O4W Ca1 C4 101.32(17) . 2_567 ? O5W Ca1 C4 71.92(16) . 2_567 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.870 _refine_diff_density_min -0.806 _refine_diff_density_rms 0.156