Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Eric V. Anslyn' 'Mark Gray' 'Vince Lynch' 'Karl Wallace' 'Z. Zhong' _publ_contact_author_name 'Dr Eric V Anslyn' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas at Austin Austin USA ; _publ_contact_author_email ? _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Manuscript Title: An Artificial Siderophore for the Detection of Iron(III) ; data_kw17 _database_code_depnum_ccdc_archive 'CCDC 273146' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 N2 O12 S2' _chemical_formula_weight 660.74 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' S S 0.1246 0.1234 '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 5.21570(10) _cell_length_b 10.1361(3) _cell_length_c 14.6002(4) _cell_angle_alpha 82.1040(10) _cell_angle_beta 82.4650(10) _cell_angle_gamma 82.137(2) _cell_volume 752.38(3) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour blue _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 350 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5486 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 27.41 _reflns_number_total 3383 _reflns_number_gt 2423 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _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. ; _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^)+(0.0484P)^2^+0.6840P] 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 3383 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.022 _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 0.5346(4) 0.5967(2) 0.48982(15) 0.0173(5) Uani 1 1 d . . . C2 C 0.3690(4) 0.5208(2) 0.44933(14) 0.0155(4) Uani 1 1 d . . . C3 C 0.1934(4) 0.5491(2) 0.38190(14) 0.0156(4) Uani 1 1 d . . . C4 C 0.1463(4) 0.6802(2) 0.33163(15) 0.0182(5) Uani 1 1 d . . . C5 C -0.0210(4) 0.7073(2) 0.26453(15) 0.0199(5) Uani 1 1 d . . . H5 H -0.0477 0.7961 0.2319 0.024 Uiso 1 1 d R . . C6 C -0.1575(4) 0.6060(2) 0.24275(15) 0.0178(5) Uani 1 1 d . . . C7 C -0.1149(4) 0.4760(2) 0.29136(15) 0.0175(5) Uani 1 1 d . . . H7 H -0.2007 0.4053 0.2762 0.021 Uiso 1 1 d R . . C8 C 0.0519(4) 0.4487(2) 0.35874(14) 0.0162(5) Uani 1 1 d . . . O9 O 0.5778(3) 0.71673(15) 0.47724(11) 0.0222(4) Uani 1 1 d . . . O10 O 0.2649(4) 0.78482(16) 0.34651(12) 0.0258(4) Uani 1 1 d . . . N11 N -0.3261(4) 0.63440(18) 0.17720(13) 0.0193(4) Uani 1 1 d . . . C12 C -0.3873(5) 0.7712(2) 0.13179(16) 0.0235(5) Uani 1 1 d . . . H12A H -0.3846 0.8330 0.1758 0.028 Uiso 1 1 d R . . H12B H -0.5598 0.7820 0.1134 0.028 Uiso 1 1 d R . . C13 C -0.1959(5) 0.8071(3) 0.04731(18) 0.0313(6) Uani 1 1 d . . . H13A H -0.2179 0.7570 -0.0017 0.038 Uiso 1 1 d R . . H13B H -0.0207 0.7841 0.0627 0.038 Uiso 1 1 d R . . O14 O -0.2427(5) 0.9451(2) 0.01608(17) 0.0585(7) Uani 1 1 d . . . H14 H -0.1193 0.9839 0.0267 0.088 Uiso 1 1 calc R . . C15 C -0.4565(4) 0.5281(2) 0.15028(16) 0.0200(5) Uani 1 1 d . . . H15A H -0.6090 0.5677 0.1217 0.024 Uiso 1 1 d R . . H15B H -0.5110 0.4709 0.2054 0.024 Uiso 1 1 d R . . C16 C -0.2798(5) 0.4428(2) 0.08403(16) 0.0243(5) Uani 1 1 d . . . H16A H -0.1206 0.4088 0.1101 0.029 Uiso 1 1 d R . . H16B H -0.2381 0.4974 0.0263 0.029 Uiso 1 1 d R . . O17 O -0.4053(4) 0.33464(19) 0.06612(14) 0.0336(4) Uani 1 1 d . . . O18 O 0.0700(3) 0.32214(16) 0.40294(12) 0.0224(4) Uani 1 1 d . . . S1A S -0.25107(13) 0.07316(6) 0.26450(5) 0.0314(2) Uani 1 1 d . . . O1A O -0.3962(4) 0.21024(18) 0.24282(14) 0.0385(5) Uani 1 1 d . . . C1A C -0.2569(6) 0.0445(3) 0.3875(2) 0.0454(8) Uani 1 1 d . . . H1AA H -0.4303 0.0313 0.4151 0.068 Uiso 1 1 d R . . H1AB H -0.1390 -0.0336 0.4047 0.068 Uiso 1 1 d R . . H1AC H -0.2053 0.1211 0.4091 0.068 Uiso 1 1 d R . . C2A C 0.0828(6) 0.0931(3) 0.2352(2) 0.0418(7) Uani 1 1 d . . . H2AA H 0.1202 0.1093 0.1687 0.063 Uiso 1 1 d R . . H2AB H 0.1214 0.1679 0.2626 0.063 Uiso 1 1 d R . . H2AC H 0.1877 0.0131 0.2582 0.063 Uiso 1 1 d R . . H18 H 0.161(6) 0.309(3) 0.435(2) 0.030(9) Uiso 1 1 d . . . H10 H 0.351(7) 0.769(3) 0.388(2) 0.055(11) Uiso 1 1 d . . . H17 H -0.413(6) 0.286(3) 0.118(2) 0.036(8) 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 C1 0.0175(11) 0.0204(11) 0.0149(11) -0.0021(9) -0.0040(8) -0.0028(9) C2 0.0164(11) 0.0158(11) 0.0144(10) -0.0016(8) -0.0019(8) -0.0025(8) C3 0.0160(11) 0.0164(11) 0.0145(11) -0.0013(8) -0.0027(8) -0.0021(8) C4 0.0201(11) 0.0178(11) 0.0182(11) -0.0014(9) -0.0059(9) -0.0047(9) C5 0.0240(12) 0.0159(11) 0.0202(12) 0.0003(9) -0.0080(9) -0.0019(9) C6 0.0167(11) 0.0208(12) 0.0159(11) -0.0012(9) -0.0039(9) -0.0016(9) C7 0.0171(11) 0.0190(11) 0.0179(11) -0.0024(9) -0.0044(9) -0.0052(9) C8 0.0174(11) 0.0152(11) 0.0157(11) 0.0000(8) -0.0018(8) -0.0025(8) O9 0.0287(9) 0.0153(8) 0.0253(9) 0.0010(6) -0.0133(7) -0.0058(7) O10 0.0351(10) 0.0173(8) 0.0296(10) 0.0015(7) -0.0218(8) -0.0066(7) N11 0.0217(10) 0.0187(10) 0.0195(10) -0.0002(8) -0.0104(8) -0.0042(8) C12 0.0228(12) 0.0235(12) 0.0264(13) 0.0006(10) -0.0129(10) -0.0039(10) C13 0.0341(15) 0.0287(14) 0.0324(14) 0.0026(11) -0.0080(11) -0.0110(11) O14 0.0787(18) 0.0329(12) 0.0625(15) 0.0153(11) -0.0119(13) -0.0191(11) C15 0.0183(11) 0.0241(12) 0.0195(11) -0.0008(9) -0.0084(9) -0.0050(9) C16 0.0254(13) 0.0273(13) 0.0218(12) -0.0025(10) -0.0064(10) -0.0055(10) O17 0.0458(12) 0.0283(10) 0.0317(11) -0.0072(9) -0.0127(9) -0.0097(8) O18 0.0277(9) 0.0185(9) 0.0240(9) 0.0034(7) -0.0156(8) -0.0070(7) S1A 0.0353(4) 0.0243(3) 0.0367(4) -0.0013(3) -0.0098(3) -0.0075(3) O1A 0.0363(11) 0.0281(10) 0.0515(12) 0.0033(9) -0.0146(9) -0.0041(8) C1A 0.059(2) 0.0352(17) 0.0367(17) 0.0024(13) 0.0039(14) -0.0028(14) C2A 0.0364(16) 0.0368(16) 0.0485(18) 0.0027(13) 0.0010(13) -0.0049(13) _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 O9 1.252(3) . ? C1 C2 1.457(3) 2_666 ? C1 C2 1.459(3) . ? C1 C1 2.016(4) 2_666 ? C2 C3 1.406(3) . ? C2 C1 1.457(3) 2_666 ? C3 C4 1.434(3) . ? C3 C8 1.436(3) . ? C4 O10 1.354(3) . ? C4 C5 1.372(3) . ? C5 C6 1.418(3) . ? C5 H5 0.9599 . ? C6 N11 1.359(3) . ? C6 C7 1.412(3) . ? C7 C8 1.373(3) . ? C7 H7 0.9601 . ? C8 O18 1.351(3) . ? O10 H10 0.79(4) . ? N11 C12 1.465(3) . ? N11 C15 1.471(3) . ? C12 C13 1.518(4) . ? C12 H12A 0.9599 . ? C12 H12B 0.9600 . ? C13 O14 1.408(3) . ? C13 H13A 0.9601 . ? C13 H13B 0.9600 . ? O14 H14 0.8400 . ? C15 C16 1.520(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 O17 1.421(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? O17 H17 0.85(3) . ? O18 H18 0.70(3) . ? S1A O1A 1.5027(19) . ? S1A C2A 1.770(3) . ? S1A C1A 1.776(3) . ? C1A H1AA 0.9600 . ? C1A H1AB 0.9600 . ? C1A H1AC 0.9601 . ? C2A H2AA 0.9599 . ? C2A H2AB 0.9600 . ? C2A H2AC 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 C1 C2 133.6(2) . 2_666 ? O9 C1 C2 133.9(2) . . ? C2 C1 C2 92.50(17) 2_666 . ? O9 C1 C1 179.9(3) . 2_666 ? C2 C1 C1 46.29(12) 2_666 2_666 ? C2 C1 C1 46.21(12) . 2_666 ? C3 C2 C1 136.4(2) . 2_666 ? C3 C2 C1 136.1(2) . . ? C1 C2 C1 87.50(17) 2_666 . ? C2 C3 C4 121.87(19) . . ? C2 C3 C8 122.19(19) . . ? C4 C3 C8 115.93(18) . . ? O10 C4 C5 115.65(19) . . ? O10 C4 C3 122.43(18) . . ? C5 C4 C3 121.9(2) . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.2 . . ? N11 C6 C7 121.2(2) . . ? N11 C6 C5 120.5(2) . . ? C7 C6 C5 118.26(19) . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.6 . . ? O18 C8 C7 115.68(19) . . ? O18 C8 C3 122.30(18) . . ? C7 C8 C3 122.01(19) . . ? C4 O10 H10 114(2) . . ? C6 N11 C12 121.59(18) . . ? C6 N11 C15 120.79(18) . . ? C12 N11 C15 117.62(17) . . ? N11 C12 C13 113.1(2) . . ? N11 C12 H12A 108.7 . . ? C13 C12 H12A 108.3 . . ? N11 C12 H12B 109.5 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 108.0 . . ? O14 C13 C12 109.9(2) . . ? O14 C13 H13A 108.9 . . ? C12 C13 H13A 109.4 . . ? O14 C13 H13B 110.5 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 O14 H14 109.5 . . ? N11 C15 C16 112.55(18) . . ? N11 C15 H15A 109.5 . . ? C16 C15 H15A 109.4 . . ? N11 C15 H15B 108.7 . . ? C16 C15 H15B 108.5 . . ? H15A C15 H15B 108.1 . . ? O17 C16 C15 110.74(19) . . ? O17 C16 H16A 109.9 . . ? C15 C16 H16A 109.8 . . ? O17 C16 H16B 108.8 . . ? C15 C16 H16B 109.1 . . ? H16A C16 H16B 108.4 . . ? C16 O17 H17 103(2) . . ? C8 O18 H18 114(2) . . ? O1A S1A C2A 105.52(12) . . ? O1A S1A C1A 106.22(13) . . ? C2A S1A C1A 98.64(16) . . ? S1A C1A H1AA 109.3 . . ? S1A C1A H1AB 109.9 . . ? H1AA C1A H1AB 109.5 . . ? S1A C1A H1AC 109.2 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? S1A C2A H2AA 109.4 . . ? S1A C2A H2AB 109.4 . . ? H2AA C2A H2AB 109.5 . . ? S1A C2A H2AC 109.6 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 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 O9 C1 C2 C3 -0.4(5) . . . . ? C2 C1 C2 C3 179.7(3) 2_666 . . . ? C1 C1 C2 C3 179.7(3) 2_666 . . . ? O9 C1 C2 C1 180.0(3) . . . 2_666 ? C2 C1 C2 C1 0.0 2_666 . . 2_666 ? C1 C2 C3 C4 -178.5(2) 2_666 . . . ? C1 C2 C3 C4 2.0(4) . . . . ? C1 C2 C3 C8 1.1(4) 2_666 . . . ? C1 C2 C3 C8 -178.4(2) . . . . ? C2 C3 C4 O10 -0.8(3) . . . . ? C8 C3 C4 O10 179.6(2) . . . . ? C2 C3 C4 C5 178.7(2) . . . . ? C8 C3 C4 C5 -0.9(3) . . . . ? O10 C4 C5 C6 -179.8(2) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 N11 178.9(2) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? N11 C6 C7 C8 -178.7(2) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? C6 C7 C8 O18 177.66(19) . . . . ? C6 C7 C8 C3 -1.1(3) . . . . ? C2 C3 C8 O18 2.9(3) . . . . ? C4 C3 C8 O18 -177.54(19) . . . . ? C2 C3 C8 C7 -178.5(2) . . . . ? C4 C3 C8 C7 1.1(3) . . . . ? C7 C6 N11 C12 175.0(2) . . . . ? C5 C6 N11 C12 -4.5(3) . . . . ? C7 C6 N11 C15 -4.2(3) . . . . ? C5 C6 N11 C15 176.4(2) . . . . ? C6 N11 C12 C13 86.4(3) . . . . ? C15 N11 C12 C13 -94.4(2) . . . . ? N11 C12 C13 O14 -171.0(2) . . . . ? C6 N11 C15 C16 -78.5(3) . . . . ? C12 N11 C15 C16 102.3(2) . . . . ? N11 C15 C16 O17 174.99(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O14 H14 O14 0.84 2.10 2.861(5) 150.4 2_575 O18 H18 O9 0.70(3) 1.96(3) 2.654(2) 177(3) 2_666 O10 H10 O9 0.79(4) 1.85(4) 2.633(2) 173(4) . O17 H17 O1A 0.85(3) 1.88(3) 2.715(3) 166(3) . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.41 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.687 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.065