Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2002 data_shel93 _database_code_CSD 186435 _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Kiss, T.' 'Hozlowski, H.' 'Kilyen, M.' 'Labadi, I.' 'Lakatos, A.' 'Latajka, R.' 'Raptopoulou, Catherine' 'Salifoglou, A.' _publ_contact_author_name 'Prof T Kiss' _publ_contact_author_address ; Biocoordination Chemistry Research Group of the Hungarian Academy of Sciences University of Szeged P.O Box 440 Szeged H-6701 HUNGARY ; _publ_contact_author_email 'TKISS@CHEM.U-SZEGED.HU' _publ_section_title ; AI(III)-binding properties of iminodiacetic acid, nitrilotriacetic acid and its mixed carboxylic-phosphonic derivatives ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H16 Al K N2 O11' _chemical_formula_weight 382.31 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'K' 'K' 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Al' 'Al' 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M Pnab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y, z' _cell_length_a 15.352(8) _cell_length_b 10.392(6) _cell_length_c 18.54(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2958(1) _cell_formula_units_Z 8 _cell_measurement_temperature 298 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.3 _cell_measurement_theta_max 11.6 _exptl_crystal_description 'parallelipiped' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 1.70 _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'floating method' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type 'psi-scan empirical' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Crystal Logic Dual Goniometer' _diffrn_measurement_method 'theta-2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.3 _diffrn_reflns_number 2609 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2608 _reflns_number_observed 2362 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Program COLLECT (UCLA Crystallographic package, C.E.Strouse 1994)' _computing_cell_refinement 'Program LEAST (UCLA Crystallographic package, C.E.Strouse 1994)' _computing_data_reduction 'Program REDUCE (UCLA Crystallographic package, C.E.Strouse 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0002P)^2^+6.3702P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2608 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_obs 0.0488 _refine_ls_wR_factor_all 0.1319 _refine_ls_wR_factor_obs 0.1290 _refine_ls_goodness_of_fit_all 1.220 _refine_ls_goodness_of_fit_obs 1.261 _refine_ls_restrained_S_all 1.220 _refine_ls_restrained_S_obs 1.261 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al Al 0.59760(6) 0.00854(9) 0.75631(5) 0.0248(2) Uani 1 d . . O1 O 0.49699(15) -0.0183(2) 0.70109(12) 0.0320(5) Uani 1 d . . O3 O 0.5532(2) 0.1362(2) 0.81634(13) 0.0339(6) Uani 1 d . . N1 N 0.5383(2) -0.1160(3) 0.8262(2) 0.0302(6) Uani 1 d . . O5 O 0.6345(2) 0.1318(2) 0.69068(12) 0.0326(5) Uani 1 d . . O7 O 0.6981(2) 0.0048(3) 0.81291(13) 0.0377(6) Uani 1 d . . N2 N 0.6664(2) -0.1179(3) 0.6929(2) 0.0289(6) Uani 1 d . . C1 C 0.4352(2) -0.0918(3) 0.7247(2) 0.0298(7) Uani 1 d . . O2 O 0.3666(2) -0.1094(3) 0.69367(14) 0.0433(7) Uani 1 d . . C2 C 0.4544(2) -0.1597(4) 0.7953(2) 0.0336(8) Uani 1 d . . C3 C 0.5292(3) -0.0422(4) 0.8941(2) 0.0435(9) Uani 1 d . . C4 C 0.5306(2) 0.1011(4) 0.8802(2) 0.0341(8) Uani 1 d . . O4 O 0.5125(2) 0.1768(3) 0.92888(15) 0.0531(8) Uani 1 d . . C5 C 0.6637(2) 0.0917(4) 0.6294(2) 0.0336(8) Uani 1 d . . O6 O 0.6801(2) 0.1635(3) 0.57937(14) 0.0488(7) Uani 1 d . . C6 C 0.6737(3) -0.0522(4) 0.6219(2) 0.0409(9) Uani 1 d . . C7 C 0.7512(2) -0.1466(4) 0.7280(2) 0.0360(8) Uani 1 d . . C8 C 0.7622(2) -0.0707(3) 0.7966(2) 0.0359(8) Uani 1 d . . O8 O 0.8276(2) -0.0828(3) 0.8337(2) 0.0510(8) Uani 1 d . . K K 0.35079(5) -0.22967(9) 0.56117(4) 0.0431(3) Uani 1 d . . OW1 O 0.3658(5) 0.2489(5) 0.5337(3) 0.146(3) Uani 1 d . . OW2 O 0.4400(3) 0.0167(5) 0.5533(2) 0.105(2) Uani 1 d . . OW3 O 0.2561(13) -0.4366(6) 0.4839(4) 0.074(3) Uani 0.50 d P . OW4 O 0.2451(10) -0.6561(11) 0.5693(6) 0.148(5) Uani 0.50 d P . HN1 H 0.5689(26) -0.1905(40) 0.8319(22) 0.044(11) Uiso 1 d . . HN2 H 0.6414(22) -0.1845(36) 0.6866(18) 0.023(9) Uiso 1 d . . H2A H 0.4118(23) -0.1414(34) 0.8296(20) 0.031(9) Uiso 1 d . . H2B H 0.4557(24) -0.2509(38) 0.7852(20) 0.036(10) Uiso 1 d . . H3A H 0.5778(30) -0.0652(44) 0.9256(25) 0.060(13) Uiso 1 d . . H3B H 0.4790(33) -0.0590(47) 0.9166(26) 0.065(15) Uiso 1 d . . H6A H 0.6227(27) -0.0867(40) 0.5920(22) 0.047(11) Uiso 1 d . . H6B H 0.7246(28) -0.0794(40) 0.5977(22) 0.048(12) Uiso 1 d . . H7A H 0.7549(25) -0.2367(37) 0.7465(21) 0.038(10) Uiso 1 d . . H7B H 0.8002(28) -0.1272(42) 0.6978(23) 0.052(12) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al 0.0254(5) 0.0212(5) 0.0278(5) 0.0017(4) 0.0018(4) 0.0001(4) O1 0.0288(12) 0.0370(13) 0.0302(12) 0.0037(10) -0.0015(10) -0.0010(10) O3 0.0387(13) 0.0263(12) 0.0366(13) -0.0033(10) 0.0040(11) 0.0025(10) N1 0.0329(15) 0.0246(14) 0.0331(15) 0.0043(12) 0.0014(12) 0.0012(12) O5 0.0383(13) 0.0255(12) 0.0340(13) 0.0047(10) 0.0048(10) -0.0028(10) O7 0.0316(13) 0.0440(14) 0.0374(13) -0.0019(12) -0.0052(11) 0.0002(11) N2 0.0288(15) 0.0211(14) 0.037(2) -0.0010(12) 0.0009(12) -0.0007(12) C1 0.028(2) 0.027(2) 0.035(2) -0.0072(14) 0.0039(14) -0.0001(14) O2 0.0310(13) 0.052(2) 0.0470(15) -0.0097(13) -0.0056(12) -0.0061(12) C2 0.031(2) 0.032(2) 0.039(2) 0.001(2) 0.006(2) -0.0035(15) C3 0.054(2) 0.048(2) 0.028(2) 0.000(2) 0.005(2) -0.009(2) C4 0.029(2) 0.042(2) 0.032(2) -0.007(2) 0.0000(14) 0.002(2) O4 0.051(2) 0.062(2) 0.046(2) -0.0220(15) 0.0052(13) 0.0087(14) C5 0.027(2) 0.041(2) 0.033(2) 0.009(2) -0.0025(14) -0.0034(15) O6 0.048(2) 0.060(2) 0.0390(14) 0.0229(14) 0.0005(12) -0.0071(14) C6 0.047(2) 0.046(2) 0.030(2) -0.001(2) 0.005(2) 0.012(2) C7 0.029(2) 0.035(2) 0.044(2) 0.007(2) 0.003(2) 0.006(2) C8 0.028(2) 0.035(2) 0.045(2) 0.014(2) 0.000(2) -0.0049(15) O8 0.0382(15) 0.057(2) 0.058(2) 0.0183(15) -0.0182(13) -0.0031(13) K 0.0398(5) 0.0574(5) 0.0321(4) 0.0056(4) -0.0003(3) 0.0096(4) OW1 0.252(8) 0.099(4) 0.088(3) -0.013(3) 0.053(4) -0.054(4) OW2 0.110(3) 0.145(4) 0.059(2) 0.028(3) -0.013(2) -0.037(3) OW3 0.111(7) 0.059(3) 0.054(8) 0.008(3) 0.004(8) 0.007(5) OW4 0.233(14) 0.123(8) 0.089(7) 0.002(6) -0.009(8) -0.076(10) _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 Al O5 1.856(2) . ? Al O3 1.861(3) . ? Al O7 1.867(3) . ? Al O1 1.874(3) . ? Al N1 2.045(3) . ? Al N2 2.056(3) . ? O1 C1 1.294(4) . ? O3 C4 1.286(4) . ? N1 C3 1.481(5) . ? N1 C2 1.482(4) . ? O5 C5 1.291(4) . ? O7 C8 1.294(4) . ? N2 C7 1.486(4) . ? N2 C6 1.486(5) . ? C1 O2 1.214(4) . ? C1 C2 1.515(5) . ? O2 K 2.767(3) . ? C3 C4 1.511(6) . ? C4 O4 1.230(4) . ? C4 K 3.449(4) 6_567 ? O4 K 2.672(3) 6_567 ? C5 O6 1.217(4) . ? C5 C6 1.510(5) . ? C5 K 3.450(4) 8_655 ? O6 K 2.729(3) 8_655 ? O6 K 2.737(3) 5_656 ? C7 C8 1.508(5) . ? C8 O8 1.222(4) . ? O8 K 2.780(3) 3_546 ? K O4 2.672(3) 6_557 ? K O6 2.729(3) 8 ? K O6 2.737(3) 5_656 ? K O8 2.780(3) 3_446 ? K OW3 2.831(14) 4_556 ? K OW2 2.908(5) . ? K OW3 2.965(14) . ? K C4 3.449(4) 6_557 ? K C5 3.450(4) 8 ? K K 3.837(2) 4_556 ? OW3 OW3 0.627(14) 4_556 ? OW3 K 2.831(14) 4_556 ? 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 O5 Al O3 90.69(12) . . ? O5 Al O7 97.52(12) . . ? O3 Al O7 88.93(12) . . ? O5 Al O1 89.78(11) . . ? O3 Al O1 97.54(12) . . ? O7 Al O1 170.20(12) . . ? O5 Al N1 171.24(12) . . ? O3 Al N1 84.76(12) . . ? O7 Al N1 89.90(12) . . ? O1 Al N1 83.41(12) . . ? O5 Al N2 84.78(12) . . ? O3 Al N2 170.42(12) . . ? O7 Al N2 83.31(12) . . ? O1 Al N2 90.90(12) . . ? N1 Al N2 100.78(13) . . ? C1 O1 Al 120.5(2) . . ? C4 O3 Al 116.6(2) . . ? C3 N1 C2 113.9(3) . . ? C3 N1 Al 104.7(2) . . ? C2 N1 Al 109.6(2) . . ? C5 O5 Al 117.4(2) . . ? C8 O7 Al 120.7(2) . . ? C7 N2 C6 114.5(3) . . ? C7 N2 Al 109.2(2) . . ? C6 N2 Al 104.6(2) . . ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 120.5(3) . . ? O1 C1 C2 115.2(3) . . ? C1 O2 K 124.4(2) . . ? N1 C2 C1 111.1(3) . . ? N1 C3 C4 111.3(3) . . ? O4 C4 O3 123.8(4) . . ? O4 C4 C3 120.1(3) . . ? O3 C4 C3 116.2(3) . . ? O4 C4 K 42.3(2) . 6_567 ? O3 C4 K 111.2(2) . 6_567 ? C3 C4 K 115.9(2) . 6_567 ? C4 O4 K 119.6(2) . 6_567 ? O6 C5 O5 123.0(4) . . ? O6 C5 C6 121.1(3) . . ? O5 C5 C6 115.8(3) . . ? O6 C5 K 45.0(2) . 8_655 ? O5 C5 K 118.6(2) . 8_655 ? C6 C5 K 107.1(2) . 8_655 ? C5 O6 K 116.6(2) . 8_655 ? C5 O6 K 147.6(3) . 5_656 ? K O6 K 89.18(8) 8_655 5_656 ? N2 C6 C5 111.5(3) . . ? N2 C7 C8 111.3(3) . . ? O8 C8 O7 123.7(4) . . ? O8 C8 C7 120.9(3) . . ? O7 C8 C7 115.4(3) . . ? C8 O8 K 124.8(2) . 3_546 ? O4 K O6 167.08(9) 6_557 8 ? O4 K O6 108.56(9) 6_557 5_656 ? O6 K O6 83.57(10) 8 5_656 ? O4 K O2 91.23(9) 6_557 . ? O6 K O2 81.99(8) 8 . ? O6 K O2 138.35(10) 5_656 . ? O4 K O8 79.37(8) 6_557 3_446 ? O6 K O8 88.10(9) 8 3_446 ? O6 K O8 145.27(10) 5_656 3_446 ? O2 K O8 72.85(10) . 3_446 ? O4 K OW3 106.4(4) 6_557 4_556 ? O6 K OW3 70.8(3) 8 4_556 ? O6 K OW3 79.0(2) 5_656 4_556 ? O2 K OW3 131.0(2) . 4_556 ? O8 K OW3 66.4(2) 3_446 4_556 ? O4 K OW2 83.46(13) 6_557 . ? O6 K OW2 103.69(13) 8 . ? O6 K OW2 79.20(10) 5_656 . ? O2 K OW2 66.77(10) . . ? O8 K OW2 135.49(11) 3_446 . ? OW3 K OW2 158.0(2) 4_556 . ? O4 K OW3 103.0(3) 6_557 . ? O6 K OW3 76.8(3) 8 . ? O6 K OW3 68.7(2) 5_656 . ? O2 K OW3 143.1(2) . . ? O8 K OW3 76.6(2) 3_446 . ? OW3 K OW3 12.1(3) 4_556 . ? OW2 K OW3 147.7(2) . . ? O4 K C4 18.07(8) 6_557 6_557 ? O6 K C4 149.05(9) 8 6_557 ? O6 K C4 124.56(9) 5_656 6_557 ? O2 K C4 83.11(9) . 6_557 ? O8 K C4 61.56(8) 3_446 6_557 ? OW3 K C4 99.8(3) 4_556 6_557 ? OW2 K C4 95.04(12) . 6_557 ? OW3 K C4 100.1(3) . 6_557 ? O4 K C5 154.03(9) 6_557 8 ? O6 K C5 18.38(8) 8 8 ? O6 K C5 95.76(9) 5_656 8 ? O2 K C5 63.88(8) . 8 ? O8 K C5 85.83(9) 3_446 8 ? OW3 K C5 86.6(3) 4_556 8 ? OW2 K C5 92.57(13) . 8 ? OW3 K C5 94.0(3) . 8 ? C4 K C5 139.67(9) 6_557 8 ? O4 K K 142.19(8) 6_557 4_556 ? O6 K K 45.49(6) 8 4_556 ? O6 K K 45.33(6) 5_656 4_556 ? O2 K K 126.56(6) . 4_556 ? O8 K K 108.14(7) 3_446 4_556 ? OW3 K K 50.1(3) 4_556 4_556 ? OW2 K K 110.50(9) . 4_556 ? OW3 K K 47.1(3) . 4_556 ? C4 K K 146.30(7) 6_557 4_556 ? C5 K K 62.96(7) 8 4_556 ? OW3 OW3 K 96.2(25) 4_556 4_556 ? OW3 OW3 K 71.7(23) 4_556 . ? K OW3 K 82.9(2) 4_556 . ? _refine_diff_density_max 0.552 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.067