data_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 I O2' _chemical_formula_weight 350.14 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.8867(5) _cell_length_b 5.6677(3) _cell_length_c 11.9084(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.440(5) _cell_angle_gamma 90.00 _cell_volume 660.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 2.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.566 _exptl_absorpt_correction_T_max 0.785 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3006 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.09 _reflns_number_total 2300 _reflns_number_gt 1987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0150P)^2^+1.7000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(5) _refine_ls_number_reflns 2300 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 I1 I 0.36215(5) 0.85186(14) 0.02253(4) 0.06026(17) Uani 1 1 d . . . O1 O -0.1284(5) -0.0921(13) 0.3285(4) 0.062(2) Uani 1 1 d . . . O2 O -0.0891(5) -0.1058(14) 0.1418(4) 0.063(2) Uani 1 1 d . . . C1 C 0.4835(6) 0.364(3) 0.2707(5) 0.0532(17) Uani 1 1 d . . . H1A H 0.4601 0.2315 0.2260 0.064 Uiso 1 1 calc R . . C2 C 0.6100(7) 0.378(3) 0.3391(7) 0.060(2) Uani 1 1 d . . . H2A H 0.6730 0.2568 0.3384 0.072 Uiso 1 1 calc R . . C3 C 0.6421(8) 0.5694(17) 0.4069(7) 0.061(2) Uani 1 1 d . . . H3A H 0.7267 0.5752 0.4527 0.073 Uiso 1 1 calc R . . C4 C 0.5534(8) 0.7519(15) 0.4095(7) 0.063(2) Uani 1 1 d . . . H4A H 0.5760 0.8802 0.4573 0.075 Uiso 1 1 calc R . . C5 C 0.4274(8) 0.7425(14) 0.3386(6) 0.0537(19) Uani 1 1 d . . . H5A H 0.3666 0.8679 0.3381 0.064 Uiso 1 1 calc R . . C6 C 0.3922(7) 0.5520(12) 0.2701(6) 0.0386(15) Uani 1 1 d . . . C7 C 0.2567(7) 0.5354(12) 0.1958(6) 0.0408(16) Uani 1 1 d . . . C8 C 0.2269(8) 0.6460(14) 0.0981(6) 0.0499(19) Uani 1 1 d . . . H8A H 0.1383 0.6307 0.0599 0.060 Uiso 1 1 calc R . . C9 C 0.1529(6) 0.370(3) 0.2357(5) 0.0432(18) Uani 1 1 d . . . C10 C 0.1296(6) 0.378(3) 0.3483(5) 0.049(2) Uani 1 1 d . . . H10A H 0.1791 0.4831 0.3984 0.059 Uiso 1 1 calc R . . C11 C 0.0333(8) 0.2304(15) 0.3870(6) 0.055(2) Uani 1 1 d . . . H11A H 0.0165 0.2349 0.4618 0.066 Uiso 1 1 calc R . . C12 C -0.0348(7) 0.0798(14) 0.3096(6) 0.0444(17) Uani 1 1 d . . . C13 C -0.0111(7) 0.0707(14) 0.2010(6) 0.0463(17) Uani 1 1 d . . . C14 C 0.0793(7) 0.2172(13) 0.1592(6) 0.0446(17) Uani 1 1 d . . . H14A H 0.0909 0.2142 0.0831 0.054 Uiso 1 1 calc R . . C15 C -0.1685(8) -0.2022(19) 0.2205(6) 0.066(3) Uani 1 1 d . . . H15A H -0.1539 -0.3712 0.2269 0.079 Uiso 1 1 calc R . . H15B H -0.2649 -0.1740 0.1948 0.079 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 0.0626(3) 0.0617(3) 0.0605(3) 0.0095(4) 0.0226(2) -0.0038(4) O1 0.051(3) 0.083(7) 0.051(3) 0.009(3) 0.009(2) -0.019(3) O2 0.064(3) 0.080(6) 0.045(2) -0.008(3) 0.011(2) -0.033(4) C1 0.041(3) 0.058(4) 0.061(4) -0.017(7) 0.006(3) -0.010(6) C2 0.042(3) 0.063(7) 0.078(5) 0.007(7) 0.012(3) 0.005(6) C3 0.036(4) 0.085(6) 0.062(5) 0.007(5) 0.010(4) -0.019(4) C4 0.059(5) 0.069(5) 0.059(5) -0.017(4) 0.005(4) -0.027(4) C5 0.051(4) 0.051(4) 0.060(5) -0.005(4) 0.009(4) -0.008(4) C6 0.035(3) 0.040(4) 0.043(4) -0.002(3) 0.015(3) -0.007(3) C7 0.038(4) 0.042(4) 0.043(4) -0.005(3) 0.009(3) -0.005(3) C8 0.051(4) 0.055(5) 0.045(4) 0.000(4) 0.008(4) -0.001(4) C9 0.029(3) 0.059(5) 0.042(3) -0.001(6) 0.006(2) 0.004(5) C10 0.043(3) 0.063(6) 0.040(3) 0.004(5) 0.002(3) -0.006(5) C11 0.044(4) 0.078(6) 0.044(4) 0.002(4) 0.010(3) -0.004(4) C12 0.033(3) 0.060(5) 0.039(4) 0.004(4) 0.004(3) -0.004(3) C13 0.040(4) 0.052(4) 0.046(4) -0.002(3) 0.000(3) -0.003(4) C14 0.042(4) 0.057(4) 0.036(4) 0.003(3) 0.011(3) 0.000(3) C15 0.061(4) 0.080(10) 0.056(4) 0.000(5) 0.010(4) -0.027(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 I1 C8 2.077(7) . ? O1 C12 1.385(9) . ? O1 C15 1.432(9) . ? O2 C13 1.390(9) . ? O2 C15 1.417(9) . ? C1 C2 1.392(9) . ? C1 C6 1.395(14) . ? C1 H1A 0.9300 . ? C2 C3 1.360(17) . ? C2 H2A 0.9300 . ? C3 C4 1.359(12) . ? C3 H3A 0.9300 . ? C4 C5 1.399(11) . ? C4 H4A 0.9300 . ? C5 C6 1.367(10) . ? C5 H5A 0.9300 . ? C6 C7 1.496(9) . ? C7 C8 1.316(9) . ? C7 C9 1.516(13) . ? C8 H8A 0.9300 . ? C9 C14 1.385(13) . ? C9 C10 1.393(8) . ? C10 C11 1.396(12) . ? C10 H10A 0.9300 . ? C11 C12 1.360(10) . ? C11 H11A 0.9300 . ? C12 C13 1.349(10) . ? C13 C14 1.366(10) . ? C14 H14A 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? 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 C12 O1 C15 105.3(5) . . ? C13 O2 C15 105.2(5) . . ? C2 C1 C6 118.9(11) . . ? C2 C1 H1A 120.5 . . ? C6 C1 H1A 120.5 . . ? C3 C2 C1 120.4(12) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C4 C3 C2 121.6(8) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 118.5(7) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 121.1(8) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C1 119.5(7) . . ? C5 C6 C7 122.0(7) . . ? C1 C6 C7 118.5(6) . . ? C8 C7 C6 123.9(7) . . ? C8 C7 C9 119.8(6) . . ? C6 C7 C9 116.2(6) . . ? C7 C8 I1 125.1(6) . . ? C7 C8 H8A 117.4 . . ? I1 C8 H8A 117.4 . . ? C14 C9 C10 120.5(10) . . ? C14 C9 C7 119.7(5) . . ? C10 C9 C7 119.8(10) . . ? C11 C10 C9 121.1(10) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C12 C11 C10 116.4(7) . . ? C12 C11 H11A 121.8 . . ? C10 C11 H11A 121.8 . . ? C13 C12 C11 122.4(7) . . ? C13 C12 O1 110.1(6) . . ? C11 C12 O1 127.4(6) . . ? C12 C13 C14 122.7(7) . . ? C12 C13 O2 110.6(6) . . ? C14 C13 O2 126.7(7) . . ? C13 C14 C9 116.7(7) . . ? C13 C14 H14A 121.6 . . ? C9 C14 H14A 121.6 . . ? O2 C15 O1 108.6(6) . . ? O2 C15 H15A 110.0 . . ? O1 C15 H15A 110.0 . . ? O2 C15 H15B 110.0 . . ? O1 C15 H15B 110.0 . . ? H15A C15 H15B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.696 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.089