data_publication_text _publ_requested_journal ACS Med.Chem.Lett. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Ikejiri, Masahiro' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Klimpel,Dennis' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Toth, Marta' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Expahbodi, Mana' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Forbes, Christopher' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Chang, Mayland' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_25 # local file ID: data_dh50_1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H9 F4 I O3 S2' _chemical_formula_sum 'C15 H9 F4 I O3 S2' _chemical_compound_source synthesized _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour 'clear colorless' _diffrn_ambient_temperature 100(2) _chemical_formula_weight 504.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_int_tables_number 14 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.9301(8) _cell_length_b 5.6351(3) _cell_length_c 18.5698(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.768(2) _cell_angle_gamma 90.00 _cell_volume 1645.28(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9915 _cell_measurement_theta_min 3.0205 _cell_measurement_theta_max 69.1903 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.036 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 18.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.06 _exptl_absorpt_correction_T_max 0.28 _exptl_absorpt_process_details 'Sheldrick, G. M. (2006). SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 19647 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 69.57 _reflns_number_total 3041 _reflns_number_gt 2981 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _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^)+(0.0269P)^2^+3.9782P] 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 3041 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 I1 I 1.201025(11) -0.33950(4) 0.104251(10) 0.01678(9) Uani 1 1 d . . . S1 S 0.63027(4) 0.52913(13) 0.11338(4) 0.01204(15) Uani 1 1 d . . . S2 S 0.72085(5) 0.78136(15) -0.02496(4) 0.01999(17) Uani 1 1 d . . . F1 F 1.07924(12) 0.0276(4) 0.31054(10) 0.0211(4) Uani 1 1 d . . . F2 F 1.16805(12) -0.2899(4) 0.26224(11) 0.0209(4) Uani 1 1 d . . . F3 F 1.08559(12) 0.1081(4) 0.02125(10) 0.0202(4) Uani 1 1 d . . . F4 F 0.99909(12) 0.4264(4) 0.07179(10) 0.0205(4) Uani 1 1 d . . . O1 O 1.00173(13) 0.4074(4) 0.22134(12) 0.0158(4) Uani 1 1 d . . . O2 O 0.61167(15) 0.5974(4) 0.18007(13) 0.0195(5) Uani 1 1 d . . . O3 O 0.59107(14) 0.3167(4) 0.07136(14) 0.0197(5) Uani 1 1 d . . . C1 C 1.03889(19) 0.2343(6) 0.19245(18) 0.0144(6) Uani 1 1 d . . . C2 C 1.12702(19) -0.1130(6) 0.21398(18) 0.0151(6) Uani 1 1 d . . . C3 C 1.08149(19) 0.0485(6) 0.23946(17) 0.0150(6) Uani 1 1 d . . . C4 C 1.13054(19) -0.0970(6) 0.14099(17) 0.0141(6) Uani 1 1 d . . . C5 C 1.08563(19) 0.0853(6) 0.09340(17) 0.0146(6) Uani 1 1 d . . . C6 C 1.04085(19) 0.2497(6) 0.11838(18) 0.0152(6) Uani 1 1 d . . . C7 C 0.91399(18) 0.4303(6) 0.19084(16) 0.0124(6) Uani 1 1 d . . . C8 C 0.8826(2) 0.6219(6) 0.21953(17) 0.0151(6) Uani 1 1 d . . . H8 H 0.9203 0.7293 0.2554 0.018 Uiso 1 1 calc R . . C9 C 0.7958(2) 0.6532(6) 0.19506(18) 0.0150(6) Uani 1 1 d . . . H9 H 0.7732 0.7816 0.2145 0.018 Uiso 1 1 calc R . . C10 C 0.74121(18) 0.4958(5) 0.14170(16) 0.0123(6) Uani 1 1 d . . . C11 C 0.7731(2) 0.3088(6) 0.11247(17) 0.0142(6) Uani 1 1 d . . . H11 H 0.7352 0.2047 0.0754 0.017 Uiso 1 1 calc R . . C12 C 0.86033(19) 0.2725(6) 0.13719(17) 0.0129(6) Uani 1 1 d . . . H12 H 0.8828 0.1432 0.1180 0.015 Uiso 1 1 calc R . . C13 C 0.5993(2) 0.7707(6) 0.04695(17) 0.0139(6) Uani 1 1 d . . . H13A H 0.5381 0.8039 0.0342 0.017 Uiso 1 1 calc R . . H13B H 0.6316 0.9137 0.0723 0.017 Uiso 1 1 calc R . . C14 C 0.61378(19) 0.7256(6) -0.02683(18) 0.0152(6) Uani 1 1 d . . . H14 H 0.5846 0.5825 -0.0568 0.018 Uiso 1 1 calc R . . C15 C 0.6190(2) 0.9375(7) -0.07520(18) 0.0207(7) Uani 1 1 d . . . H15A H 0.6123 1.0968 -0.0557 0.025 Uiso 1 1 calc R . . H15B H 0.5928 0.9208 -0.1323 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01198(12) 0.02187(13) 0.01639(12) -0.00180(7) 0.00515(8) 0.00001(7) S1 0.0081(3) 0.0128(4) 0.0138(3) 0.0010(3) 0.0024(3) 0.0008(3) S2 0.0185(4) 0.0242(4) 0.0182(4) -0.0023(3) 0.0078(3) -0.0009(3) F1 0.0190(10) 0.0341(11) 0.0102(8) 0.0037(8) 0.0053(7) 0.0056(8) F2 0.0194(10) 0.0243(10) 0.0169(9) 0.0072(8) 0.0042(7) 0.0067(8) F3 0.0193(9) 0.0322(11) 0.0087(8) 0.0019(7) 0.0048(7) 0.0003(8) F4 0.0158(9) 0.0262(10) 0.0168(9) 0.0089(8) 0.0030(7) 0.0061(8) O1 0.0084(10) 0.0208(11) 0.0139(10) -0.0054(9) -0.0008(8) 0.0004(9) O2 0.0179(11) 0.0236(12) 0.0185(11) 0.0052(9) 0.0087(9) 0.0031(9) O3 0.0102(11) 0.0149(11) 0.0292(12) -0.0007(9) 0.0018(9) -0.0009(8) C1 0.0053(13) 0.0214(16) 0.0144(14) -0.0042(12) 0.0012(11) -0.0009(12) C2 0.0094(14) 0.0185(16) 0.0132(14) 0.0027(12) -0.0006(11) -0.0015(12) C3 0.0092(14) 0.0258(17) 0.0078(13) 0.0004(12) 0.0008(11) -0.0033(12) C4 0.0084(14) 0.0186(15) 0.0145(14) -0.0036(12) 0.0032(11) -0.0016(12) C5 0.0116(14) 0.0228(16) 0.0080(13) -0.0011(12) 0.0021(11) -0.0041(12) C6 0.0079(14) 0.0196(16) 0.0140(14) 0.0034(12) -0.0007(11) -0.0018(12) C7 0.0064(14) 0.0179(15) 0.0107(13) 0.0036(11) 0.0005(11) 0.0012(11) C8 0.0150(16) 0.0149(15) 0.0127(14) -0.0025(11) 0.0020(12) -0.0029(12) C9 0.0157(16) 0.0154(16) 0.0130(14) -0.0018(11) 0.0042(12) 0.0017(12) C10 0.0082(14) 0.0160(15) 0.0097(13) 0.0027(11) -0.0002(11) 0.0005(11) C11 0.0121(15) 0.0148(15) 0.0124(14) -0.0029(11) 0.0007(11) -0.0023(12) C12 0.0116(15) 0.0136(15) 0.0119(14) -0.0017(11) 0.0025(11) 0.0015(12) C13 0.0121(14) 0.0132(15) 0.0142(14) 0.0015(11) 0.0024(11) 0.0015(12) C14 0.0097(14) 0.0180(16) 0.0146(14) -0.0017(12) 0.0006(11) -0.0002(12) C15 0.0169(16) 0.0325(19) 0.0124(14) -0.0031(13) 0.0051(12) -0.0055(14) _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 I1 C4 2.088(3) . ? S1 O2 1.439(2) . ? S1 O3 1.449(2) . ? S1 C10 1.763(3) . ? S1 C13 1.781(3) . ? S2 C14 1.827(3) . ? S2 C15 1.851(4) . ? F1 C3 1.340(3) . ? F2 C2 1.348(4) . ? F3 C5 1.346(3) . ? F4 C6 1.337(4) . ? O1 C1 1.373(4) . ? O1 C7 1.386(4) . ? C1 C3 1.382(5) . ? C1 C6 1.391(4) . ? C2 C4 1.382(4) . ? C2 C3 1.385(5) . ? C4 C5 1.384(5) . ? C5 C6 1.382(5) . ? C7 C12 1.392(4) . ? C7 C8 1.394(4) . ? C8 C9 1.379(5) . ? C8 H8 0.9500 . ? C9 C10 1.394(4) . ? C9 H9 0.9500 . ? C10 C11 1.384(4) . ? C11 C12 1.389(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.500(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.516(5) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? 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 S1 O3 118.82(15) . . ? O2 S1 C10 108.72(14) . . ? O3 S1 C10 107.29(14) . . ? O2 S1 C13 106.83(14) . . ? O3 S1 C13 107.47(14) . . ? C10 S1 C13 107.20(14) . . ? C14 S2 C15 48.69(15) . . ? C1 O1 C7 118.9(2) . . ? O1 C1 C3 119.9(3) . . ? O1 C1 C6 121.6(3) . . ? C3 C1 C6 118.3(3) . . ? F2 C2 C4 120.1(3) . . ? F2 C2 C3 118.3(3) . . ? C4 C2 C3 121.6(3) . . ? F1 C3 C1 119.3(3) . . ? F1 C3 C2 120.1(3) . . ? C1 C3 C2 120.5(3) . . ? C2 C4 C5 117.5(3) . . ? C2 C4 I1 121.0(2) . . ? C5 C4 I1 121.5(2) . . ? F3 C5 C6 118.2(3) . . ? F3 C5 C4 120.3(3) . . ? C6 C5 C4 121.5(3) . . ? F4 C6 C5 120.4(3) . . ? F4 C6 C1 119.1(3) . . ? C5 C6 C1 120.5(3) . . ? O1 C7 C12 123.3(3) . . ? O1 C7 C8 114.8(3) . . ? C12 C7 C8 121.9(3) . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.8(3) . . ? C11 C10 S1 119.5(2) . . ? C9 C10 S1 119.8(2) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 118.3(3) . . ? C11 C12 H12 120.8 . . ? C7 C12 H12 120.8 . . ? C14 C13 S1 113.4(2) . . ? C14 C13 H13A 108.9 . . ? S1 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? S1 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 118.2(3) . . ? C13 C14 S2 116.8(2) . . ? C15 C14 S2 66.46(18) . . ? C13 C14 H14 115.5 . . ? C15 C14 H14 115.5 . . ? S2 C14 H14 115.5 . . ? C14 C15 S2 64.85(18) . . ? C14 C15 H15A 117.2 . . ? S2 C15 H15A 117.2 . . ? C14 C15 H15B 117.2 . . ? S2 C15 H15B 117.2 . . ? H15A C15 H15B 114.3 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 69.57 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.014 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.102