# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Robert Singer' _publ_contact_author_email ROBERT.SINGER@SMU.CA _publ_section_title ; Removal of Metal Ions from Aqueous Solutions Using Chelating Task-Specific Ionic Liquids ; loop_ _publ_author_name 'Robert Singer' 'Tomislav Friscic' 'Jitendra R Harjani' 'Len MacGillivray' # Attachment 'deposit_new.cif' data_Ni _database_code_depnum_ccdc_archive 'CCDC 664336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ni(EDA-mim)2 dihydrate ; _chemical_name_common 'Ni(EDA-mim)2 dihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 N6 Ni O8, 2(H2 O)' _chemical_formula_sum 'C20 H32 N6 Ni1 O10' _chemical_formula_weight 575.23 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.2988(11) _cell_length_b 10.0381(10) _cell_length_c 21.557(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2445.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10018 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.861 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.7246 _exptl_absorpt_correction_T_max 0.8604 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18585 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2802 _reflns_number_gt 2187 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. All non-hydrogen atoms were treated anisotropically. Hydrogen atoms bonded to oxygen atoms were located from the final Fourier difference electron density map. The coordinates of hydrogen atoms bonded to carbon atoms were calculated using sterochemical rules applicable for the corresponding carbon atom. ; _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^)+(0.0591P)^2^+0.5751P] 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 2802 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 Ni Ni 0.0000 0.0000 0.5000 0.01535(13) Uani 1 2 d S . . O1 O 0.08510(12) 0.08492(13) 0.42750(6) 0.0242(3) Uani 1 1 d . . . O2 O 0.10495(14) 0.27746(15) 0.37744(7) 0.0365(4) Uani 1 1 d . . . O3 O -0.14354(13) -0.03106(14) 0.44210(7) 0.0258(3) Uani 1 1 d . . . O4 O -0.31112(14) 0.06338(16) 0.41145(9) 0.0446(5) Uani 1 1 d . . . O5 O -0.2292(2) -0.1967(2) 0.33779(9) 0.0729(7) Uani 1 1 d . . . N1 N -0.07914(13) 0.18896(15) 0.51023(7) 0.0159(3) Uani 1 1 d . . . N2 N -0.10988(14) 0.40754(15) 0.65242(7) 0.0215(4) Uani 1 1 d . . . N3 N -0.04111(18) 0.48622(17) 0.73797(9) 0.0275(4) Uani 1 1 d . . . C1 C -0.01595(16) 0.27802(19) 0.46652(9) 0.0221(4) Uani 1 1 d . . . H1A H 0.0335 0.3405 0.4909 0.026 Uiso 1 1 calc R . . H1B H -0.0753 0.3316 0.4438 0.026 Uiso 1 1 calc R . . C2 C 0.06323(16) 0.20753(19) 0.41918(9) 0.0212(4) Uani 1 1 d . . . C3 C -0.20448(16) 0.16916(19) 0.49213(9) 0.0209(4) Uani 1 1 d . . . H3A H -0.2359 0.2536 0.4751 0.025 Uiso 1 1 calc R . . H3B H -0.2512 0.1467 0.5295 0.025 Uiso 1 1 calc R . . C4 C -0.22050(17) 0.05925(19) 0.44408(9) 0.0227(4) Uani 1 1 d . . . C5 C -0.06923(17) 0.23545(19) 0.57507(8) 0.0201(4) Uani 1 1 d . . . H5A H 0.0154 0.2357 0.5870 0.024 Uiso 1 1 calc R . . H5B H -0.1106 0.1712 0.6024 0.024 Uiso 1 1 calc R . . C6 C -0.12047(17) 0.37475(19) 0.58647(8) 0.0221(4) Uani 1 1 d . . . H6A H -0.0769 0.4412 0.5613 0.027 Uiso 1 1 calc R . . H6B H -0.2047 0.3769 0.5739 0.027 Uiso 1 1 calc R . . C7 C -0.02171(18) 0.4766(2) 0.67788(10) 0.0230(4) Uani 1 1 d . . . H7 H 0.0441 0.5129 0.6563 0.028 Uiso 1 1 calc R . . C8 C -0.1453(2) 0.4207(2) 0.75190(11) 0.0385(6) Uani 1 1 d . . . H8 H -0.1802 0.4121 0.7918 0.046 Uiso 1 1 calc R . . C9 C -0.18793(19) 0.3715(2) 0.69842(10) 0.0326(5) Uani 1 1 d . . . H9 H -0.2586 0.3213 0.6933 0.039 Uiso 1 1 calc R . . C10 C 0.0320(2) 0.5612(3) 0.78189(11) 0.0418(6) Uani 1 1 d . . . H10A H 0.1049 0.5903 0.7612 0.063 Uiso 1 1 calc R . . H10B H 0.0521 0.5042 0.8173 0.063 Uiso 1 1 calc R . . H10C H -0.0119 0.6393 0.7965 0.063 Uiso 1 1 calc R . . H1O H -0.2105 -0.1332 0.3681 0.143 Uiso 1 1 d . . . H2O H -0.2128 -0.2760 0.3619 0.143 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 Ni 0.0145(2) 0.0130(2) 0.0185(2) -0.00043(12) -0.00088(12) 0.00120(11) O1 0.0279(7) 0.0188(7) 0.0259(7) 0.0011(5) 0.0076(6) 0.0020(6) O2 0.0428(9) 0.0312(9) 0.0355(9) 0.0133(7) 0.0172(7) 0.0075(7) O3 0.0230(7) 0.0215(7) 0.0330(8) -0.0083(6) -0.0074(6) 0.0035(6) O4 0.0358(9) 0.0344(9) 0.0635(12) -0.0133(8) -0.0309(8) 0.0063(7) O5 0.1130(19) 0.0648(14) 0.0408(12) -0.0103(10) -0.0042(11) -0.0387(13) N1 0.0138(7) 0.0149(8) 0.0191(8) -0.0011(6) -0.0009(6) -0.0006(6) N2 0.0253(8) 0.0168(8) 0.0224(8) -0.0032(6) 0.0011(7) 0.0018(7) N3 0.0313(10) 0.0281(10) 0.0231(10) -0.0060(7) -0.0026(8) 0.0002(7) C1 0.0230(10) 0.0162(9) 0.0270(11) 0.0020(8) 0.0035(8) -0.0003(8) C2 0.0188(9) 0.0216(10) 0.0232(10) 0.0014(8) 0.0007(7) -0.0001(8) C3 0.0144(9) 0.0188(9) 0.0294(10) -0.0015(8) -0.0024(7) 0.0017(7) C4 0.0198(10) 0.0205(10) 0.0278(11) 0.0008(8) -0.0046(8) -0.0022(8) C5 0.0225(9) 0.0191(9) 0.0187(9) -0.0029(7) -0.0028(7) 0.0032(8) C6 0.0266(10) 0.0200(10) 0.0196(9) -0.0034(8) -0.0031(8) 0.0022(8) C7 0.0236(10) 0.0206(10) 0.0248(11) -0.0020(8) -0.0003(8) 0.0023(8) C8 0.0431(13) 0.0456(14) 0.0269(11) -0.0058(10) 0.0113(10) -0.0107(11) C9 0.0311(12) 0.0357(12) 0.0311(12) -0.0048(9) 0.0089(9) -0.0084(9) C10 0.0471(14) 0.0474(16) 0.0310(13) -0.0146(11) -0.0104(11) -0.0032(12) _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 Ni O1 2.0232(13) 5_556 ? Ni O1 2.0232(13) . ? Ni O3 2.0701(14) 5_556 ? Ni O3 2.0701(14) . ? Ni N1 2.1086(15) . ? Ni N1 2.1086(15) 5_556 ? O1 C2 1.268(2) . ? O2 C2 1.235(2) . ? O3 C4 1.257(2) . ? O4 C4 1.243(2) . ? O5 H1O 0.9368(19) . ? O5 H2O 0.969(2) . ? N1 C5 1.478(2) . ? N1 C1 1.482(2) . ? N1 C3 1.482(2) . ? N2 C7 1.332(3) . ? N2 C9 1.376(3) . ? N2 C6 1.464(2) . ? N3 C7 1.317(3) . ? N3 C8 1.381(3) . ? N3 C10 1.465(3) . ? C1 C2 1.530(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C3 C4 1.524(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.533(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7 0.9500 . ? C8 C9 1.344(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 Ni O1 180.0 5_556 . ? O1 Ni O3 88.29(6) 5_556 5_556 ? O1 Ni O3 91.71(6) . 5_556 ? O1 Ni O3 91.71(6) 5_556 . ? O1 Ni O3 88.29(6) . . ? O3 Ni O3 180.0 5_556 . ? O1 Ni N1 95.55(5) 5_556 . ? O1 Ni N1 84.45(5) . . ? O3 Ni N1 97.68(5) 5_556 . ? O3 Ni N1 82.32(5) . . ? O1 Ni N1 84.45(5) 5_556 5_556 ? O1 Ni N1 95.55(5) . 5_556 ? O3 Ni N1 82.32(5) 5_556 5_556 ? O3 Ni N1 97.68(5) . 5_556 ? N1 Ni N1 180.000(1) . 5_556 ? C2 O1 Ni 115.19(12) . . ? C4 O3 Ni 114.39(12) . . ? H1O O5 H2O 98.14(18) . . ? C5 N1 C1 111.98(15) . . ? C5 N1 C3 111.33(14) . . ? C1 N1 C3 111.95(14) . . ? C5 N1 Ni 110.54(11) . . ? C1 N1 Ni 105.77(11) . . ? C3 N1 Ni 104.89(11) . . ? C7 N2 C9 108.62(17) . . ? C7 N2 C6 125.32(17) . . ? C9 N2 C6 126.05(17) . . ? C7 N3 C8 108.71(19) . . ? C7 N3 C10 125.4(2) . . ? C8 N3 C10 125.8(2) . . ? N1 C1 C2 115.26(16) . . ? N1 C1 H1A 108.5 . . ? C2 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? C2 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? O2 C2 O1 125.48(18) . . ? O2 C2 C1 116.51(17) . . ? O1 C2 C1 117.92(17) . . ? N1 C3 C4 112.92(15) . . ? N1 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N1 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? O4 C4 O3 125.08(19) . . ? O4 C4 C3 117.28(17) . . ? O3 C4 C3 117.58(17) . . ? N1 C5 C6 114.26(15) . . ? N1 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N2 C6 C5 109.25(15) . . ? N2 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N2 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? N3 C7 N2 108.58(19) . . ? N3 C7 H7 125.7 . . ? N2 C7 H7 125.7 . . ? C9 C8 N3 107.11(19) . . ? C9 C8 H8 126.4 . . ? N3 C8 H8 126.4 . . ? C8 C9 N2 106.96(19) . . ? C8 C9 H9 126.5 . . ? N2 C9 H9 126.5 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Ni O1 C2 -95.01(13) 5_556 . . . ? O3 Ni O1 C2 84.99(13) . . . . ? N1 Ni O1 C2 2.54(13) . . . . ? N1 Ni O1 C2 -177.46(13) 5_556 . . . ? O1 Ni O3 C4 86.00(15) 5_556 . . . ? O1 Ni O3 C4 -94.00(15) . . . . ? N1 Ni O3 C4 -9.36(14) . . . . ? N1 Ni O3 C4 170.64(14) 5_556 . . . ? O1 Ni N1 C5 50.29(12) 5_556 . . . ? O1 Ni N1 C5 -129.71(12) . . . . ? O3 Ni N1 C5 -38.72(12) 5_556 . . . ? O3 Ni N1 C5 141.28(12) . . . . ? O1 Ni N1 C1 171.71(11) 5_556 . . . ? O1 Ni N1 C1 -8.29(11) . . . . ? O3 Ni N1 C1 82.69(11) 5_556 . . . ? O3 Ni N1 C1 -97.31(11) . . . . ? O1 Ni N1 C3 -69.81(11) 5_556 . . . ? O1 Ni N1 C3 110.19(11) . . . . ? O3 Ni N1 C3 -158.82(11) 5_556 . . . ? O3 Ni N1 C3 21.18(11) . . . . ? C5 N1 C1 C2 133.06(16) . . . . ? C3 N1 C1 C2 -101.09(18) . . . . ? Ni N1 C1 C2 12.59(18) . . . . ? Ni O1 C2 O2 -179.32(16) . . . . ? Ni O1 C2 C1 4.3(2) . . . . ? N1 C1 C2 O2 171.13(17) . . . . ? N1 C1 C2 O1 -12.1(2) . . . . ? C5 N1 C3 C4 -149.43(16) . . . . ? C1 N1 C3 C4 84.37(19) . . . . ? Ni N1 C3 C4 -29.85(17) . . . . ? Ni O3 C4 O4 176.96(18) . . . . ? Ni O3 C4 C3 -5.9(2) . . . . ? N1 C3 C4 O4 -156.91(18) . . . . ? N1 C3 C4 O3 25.7(2) . . . . ? C1 N1 C5 C6 60.2(2) . . . . ? C3 N1 C5 C6 -66.0(2) . . . . ? Ni N1 C5 C6 177.87(13) . . . . ? C7 N2 C6 C5 95.1(2) . . . . ? C9 N2 C6 C5 -84.3(2) . . . . ? N1 C5 C6 N2 177.77(15) . . . . ? C8 N3 C7 N2 0.2(2) . . . . ? C10 N3 C7 N2 -176.3(2) . . . . ? C9 N2 C7 N3 -0.3(2) . . . . ? C6 N2 C7 N3 -179.69(17) . . . . ? C7 N3 C8 C9 0.0(3) . . . . ? C10 N3 C8 C9 176.4(2) . . . . ? N3 C8 C9 N2 -0.1(3) . . . . ? C7 N2 C9 C8 0.3(2) . . . . ? C6 N2 C9 C8 179.67(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.376 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.154 data_Co _database_code_depnum_ccdc_archive 'CCDC 664337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Co(EDA-mim)2 dihydrate ; _chemical_name_common 'Co(EDA-mim)2 dihydrate' _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Co N6 O8, 2(H2 O)' _chemical_formula_sum 'C20 H32 Co1 N6 O10' _chemical_formula_weight 575.45 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3066(11) _cell_length_b 10.1637(10) _cell_length_c 21.496(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2470.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9175 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 0.761 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.7504 _exptl_absorpt_correction_T_max 0.9557 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17405 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2839 _reflns_number_gt 1841 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. All non-hydrogen atoms were treated anisotropically. Hydrogen atoms bonded to oxygen atoms were located from the final Fourier difference electron density map. The coordinates of hydrogen atoms bonded to carbon atoms were calculated using sterochemical rules applicable for the corresponding carbon atom. ; _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^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2839 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 Co Co 0.0000 0.0000 0.5000 0.01777(16) Uani 1 2 d S . . O1 O 0.08492(15) 0.08841(16) 0.42774(8) 0.0279(4) Uani 1 1 d . . . O2 O 0.10251(18) 0.27708(18) 0.37633(9) 0.0413(5) Uani 1 1 d . . . O3 O -0.14683(17) -0.02641(17) 0.44152(9) 0.0289(5) Uani 1 1 d . . . O4 O -0.31287(18) 0.0686(2) 0.41061(11) 0.0504(6) Uani 1 1 d . . . O5 O -0.2294(3) -0.1927(3) 0.33776(10) 0.0784(9) Uani 1 1 d . . . N1 N -0.08174(17) 0.19236(19) 0.50968(8) 0.0180(4) Uani 1 1 d . . . N2 N -0.11006(18) 0.40786(18) 0.65305(9) 0.0242(5) Uani 1 1 d . . . N3 N -0.0408(2) 0.4848(2) 0.73883(11) 0.0304(6) Uani 1 1 d . . . C1 C -0.0189(2) 0.2788(2) 0.46546(12) 0.0240(6) Uani 1 1 d . . . H1A H 0.0297 0.3417 0.4895 0.029 Uiso 1 1 calc R . . H1B H -0.0785 0.3304 0.4421 0.029 Uiso 1 1 calc R . . C2 C 0.0611(2) 0.2091(2) 0.41868(12) 0.0246(6) Uani 1 1 d . . . C3 C -0.2068(2) 0.1718(3) 0.49170(11) 0.0232(6) Uani 1 1 d . . . H3A H -0.2389 0.2551 0.4749 0.028 Uiso 1 1 calc R . . H3B H -0.2531 0.1490 0.5293 0.028 Uiso 1 1 calc R . . C4 C -0.2230(2) 0.0636(2) 0.44338(12) 0.0260(6) Uani 1 1 d . . . C5 C -0.0703(2) 0.2383(2) 0.57466(11) 0.0223(6) Uani 1 1 d . . . H5A H 0.0146 0.2388 0.5860 0.027 Uiso 1 1 calc R . . H5B H -0.1107 0.1747 0.6023 0.027 Uiso 1 1 calc R . . C6 C -0.1214(2) 0.3755(2) 0.58661(11) 0.0254(6) Uani 1 1 d . . . H6A H -0.0783 0.4414 0.5614 0.031 Uiso 1 1 calc R . . H6B H -0.2058 0.3776 0.5743 0.031 Uiso 1 1 calc R . . C7 C -0.0218(2) 0.4765(2) 0.67840(13) 0.0251(6) Uani 1 1 d . . . H7 H 0.0435 0.5131 0.6567 0.030 Uiso 1 1 calc R . . C8 C -0.1441(3) 0.4191(3) 0.75308(14) 0.0427(8) Uani 1 1 d . . . H8 H -0.1783 0.4096 0.7932 0.051 Uiso 1 1 calc R . . C9 C -0.1870(3) 0.3712(3) 0.69944(13) 0.0373(7) Uani 1 1 d . . . H9 H -0.2575 0.3213 0.6945 0.045 Uiso 1 1 calc R . . C10 C 0.0323(3) 0.5593(3) 0.78252(14) 0.0462(8) Uani 1 1 d . . . H10A H 0.1040 0.5899 0.7613 0.069 Uiso 1 1 calc R . . H10B H 0.0543 0.5027 0.8176 0.069 Uiso 1 1 calc R . . H10C H -0.0124 0.6352 0.7979 0.069 Uiso 1 1 calc R . . H2O H -0.2200 -0.2715 0.3689 0.115 Uiso 1 1 d . . . H1O H -0.2123 -0.1277 0.3666 0.115 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 Co 0.0165(3) 0.0149(3) 0.0219(3) -0.00079(18) -0.0009(2) 0.00105(19) O1 0.0311(11) 0.0202(10) 0.0322(11) 0.0022(7) 0.0090(8) 0.0032(8) O2 0.0488(13) 0.0361(12) 0.0390(12) 0.0150(9) 0.0187(10) 0.0102(10) O3 0.0240(10) 0.0248(10) 0.0378(11) -0.0096(8) -0.0079(8) 0.0043(8) O4 0.0410(13) 0.0385(13) 0.0716(16) -0.0153(11) -0.0366(12) 0.0087(10) O5 0.119(2) 0.0717(17) 0.0446(16) -0.0124(12) -0.0043(14) -0.0412(17) N1 0.0147(10) 0.0171(10) 0.0221(11) -0.0013(8) 0.0000(8) 0.0006(9) N2 0.0281(12) 0.0189(11) 0.0257(12) -0.0034(9) 0.0011(9) 0.0007(10) N3 0.0327(13) 0.0325(13) 0.0260(13) -0.0060(10) -0.0029(11) 0.0003(10) C1 0.0257(15) 0.0169(13) 0.0295(15) 0.0026(11) 0.0052(11) 0.0003(11) C2 0.0230(14) 0.0263(15) 0.0244(14) 0.0005(11) 0.0007(11) 0.0000(12) C3 0.0163(13) 0.0206(13) 0.0326(15) -0.0003(11) -0.0009(11) 0.0015(10) C4 0.0209(14) 0.0233(14) 0.0338(15) 0.0015(12) -0.0062(12) -0.0020(12) C5 0.0238(13) 0.0188(13) 0.0244(13) -0.0029(10) -0.0025(11) 0.0029(11) C6 0.0297(15) 0.0225(13) 0.0241(14) -0.0032(11) -0.0036(11) 0.0016(12) C7 0.0260(15) 0.0220(14) 0.0274(14) -0.0035(11) -0.0004(11) 0.0015(11) C8 0.049(2) 0.0494(19) 0.0295(16) -0.0064(15) 0.0114(15) -0.0120(17) C9 0.0369(18) 0.0377(16) 0.0373(17) -0.0068(14) 0.0117(13) -0.0103(13) C10 0.051(2) 0.053(2) 0.0340(18) -0.0165(16) -0.0128(15) -0.0033(17) _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 Co O1 2.0352(16) . ? Co O1 2.0352(16) 5_556 ? Co O3 2.0996(18) . ? Co O3 2.0996(18) 5_556 ? Co N1 2.1725(19) 5_556 ? Co N1 2.1725(19) . ? O1 C2 1.271(3) . ? O2 C2 1.235(3) . ? O3 C4 1.257(3) . ? O4 C4 1.238(3) . ? O5 H2O 1.050(3) . ? O5 H1O 0.926(2) . ? N1 C1 1.476(3) . ? N1 C5 1.479(3) . ? N1 C3 1.481(3) . ? N2 C7 1.334(3) . ? N2 C9 1.375(3) . ? N2 C6 1.471(3) . ? N3 C7 1.319(4) . ? N3 C8 1.379(4) . ? N3 C10 1.463(4) . ? C1 C2 1.527(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C3 C4 1.524(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.532(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7 0.9500 . ? C8 C9 1.343(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 Co O1 180.0 . 5_556 ? O1 Co O3 88.42(7) . . ? O1 Co O3 91.58(7) 5_556 . ? O1 Co O3 91.58(7) . 5_556 ? O1 Co O3 88.42(7) 5_556 5_556 ? O3 Co O3 180.00(8) . 5_556 ? O1 Co N1 97.10(7) . 5_556 ? O1 Co N1 82.90(7) 5_556 5_556 ? O3 Co N1 99.44(7) . 5_556 ? O3 Co N1 80.56(7) 5_556 5_556 ? O1 Co N1 82.90(7) . . ? O1 Co N1 97.10(7) 5_556 . ? O3 Co N1 80.56(7) . . ? O3 Co N1 99.44(7) 5_556 . ? N1 Co N1 180.00(10) 5_556 . ? C2 O1 Co 116.29(15) . . ? C4 O3 Co 115.45(16) . . ? H2O O5 H1O 95.5(2) . . ? C1 N1 C5 112.22(19) . . ? C1 N1 C3 112.05(18) . . ? C5 N1 C3 112.02(18) . . ? C1 N1 Co 105.62(13) . . ? C5 N1 Co 109.72(14) . . ? C3 N1 Co 104.72(14) . . ? C7 N2 C9 108.6(2) . . ? C7 N2 C6 125.4(2) . . ? C9 N2 C6 126.0(2) . . ? C7 N3 C8 109.0(2) . . ? C7 N3 C10 125.0(3) . . ? C8 N3 C10 125.9(3) . . ? N1 C1 C2 115.7(2) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? O2 C2 O1 124.9(2) . . ? O2 C2 C1 116.8(2) . . ? O1 C2 C1 118.2(2) . . ? N1 C3 C4 113.2(2) . . ? N1 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N1 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O4 C4 O3 125.1(2) . . ? O4 C4 C3 117.2(2) . . ? O3 C4 C3 117.7(2) . . ? N1 C5 C6 114.39(19) . . ? N1 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? N1 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N2 C6 C5 109.46(19) . . ? N2 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N2 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? N3 C7 N2 108.3(2) . . ? N3 C7 H7 125.9 . . ? N2 C7 H7 125.9 . . ? C9 C8 N3 106.9(3) . . ? C9 C8 H8 126.5 . . ? N3 C8 H8 126.5 . . ? C8 C9 N2 107.2(3) . . ? C8 C9 H9 126.4 . . ? N2 C9 H9 126.4 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co O1 C2 82.05(18) . . . . ? O3 Co O1 C2 -97.95(18) 5_556 . . . ? N1 Co O1 C2 -178.63(17) 5_556 . . . ? N1 Co O1 C2 1.37(17) . . . . ? O1 Co O3 C4 -92.42(19) . . . . ? O1 Co O3 C4 87.58(19) 5_556 . . . ? N1 Co O3 C4 170.65(19) 5_556 . . . ? N1 Co O3 C4 -9.35(19) . . . . ? O1 Co N1 C1 -7.37(15) . . . . ? O1 Co N1 C1 172.63(15) 5_556 . . . ? O3 Co N1 C1 -96.95(15) . . . . ? O3 Co N1 C1 83.05(15) 5_556 . . . ? O1 Co N1 C5 -128.53(16) . . . . ? O1 Co N1 C5 51.47(16) 5_556 . . . ? O3 Co N1 C5 141.89(16) . . . . ? O3 Co N1 C5 -38.11(16) 5_556 . . . ? O1 Co N1 C3 111.08(14) . . . . ? O1 Co N1 C3 -68.92(14) 5_556 . . . ? O3 Co N1 C3 21.50(14) . . . . ? O3 Co N1 C3 -158.50(14) 5_556 . . . ? C5 N1 C1 C2 131.5(2) . . . . ? C3 N1 C1 C2 -101.5(2) . . . . ? Co N1 C1 C2 12.0(2) . . . . ? Co O1 C2 O2 -178.5(2) . . . . ? Co O1 C2 C1 5.4(3) . . . . ? N1 C1 C2 O2 171.0(2) . . . . ? N1 C1 C2 O1 -12.5(3) . . . . ? C1 N1 C3 C4 83.3(2) . . . . ? C5 N1 C3 C4 -149.6(2) . . . . ? Co N1 C3 C4 -30.7(2) . . . . ? Co O3 C4 O4 176.8(2) . . . . ? Co O3 C4 C3 -6.2(3) . . . . ? N1 C3 C4 O4 -156.0(2) . . . . ? N1 C3 C4 O3 26.8(3) . . . . ? C1 N1 C5 C6 61.0(3) . . . . ? C3 N1 C5 C6 -66.0(3) . . . . ? Co N1 C5 C6 178.10(17) . . . . ? C7 N2 C6 C5 95.2(3) . . . . ? C9 N2 C6 C5 -83.8(3) . . . . ? N1 C5 C6 N2 177.3(2) . . . . ? C8 N3 C7 N2 0.3(3) . . . . ? C10 N3 C7 N2 -176.0(2) . . . . ? C9 N2 C7 N3 -0.3(3) . . . . ? C6 N2 C7 N3 -179.4(2) . . . . ? C7 N3 C8 C9 -0.1(3) . . . . ? C10 N3 C8 C9 176.1(3) . . . . ? N3 C8 C9 N2 0.0(3) . . . . ? C7 N2 C9 C8 0.2(3) . . . . ? C6 N2 C9 C8 179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.397 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.148