# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12085 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 F3 I O3' _chemical_formula_sum 'C11 H10 F3 I O3' _chemical_formula_weight 374.09 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' F F 0.0171 0.0103 '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)/n 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 5.7763(13) _cell_length_b 16.159(4) _cell_length_c 13.284(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.205(4) _cell_angle_gamma 90.00 _cell_volume 1234.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 892 _cell_measurement_theta_min 3.759 _cell_measurement_theta_max 28.350 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.012 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.629 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.554 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 6881 reflections(SADABS);Rint 0.1214 before correction and 0.0354 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker Apex 2000 CCD area detector' _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 9448 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2422 _reflns_number_gt 2237 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0453P)^2^+5.1652P] 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 2422 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0938 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.04139(5) 0.624746(17) 0.55417(2) 0.02056(13) Uani 1 1 d . . . F1 F -0.3136(14) 0.8982(3) 0.6013(4) 0.106(2) Uani 1 1 d . . . F2 F -0.0519(9) 0.9201(3) 0.5145(5) 0.0890(17) Uani 1 1 d . . . F3 F -0.3701(12) 0.9077(3) 0.4397(4) 0.107(2) Uani 1 1 d . . . O1 O 0.1874(6) 0.51223(19) 0.5734(2) 0.0248(7) Uani 1 1 d . . . O2 O -0.0299(7) 0.7604(2) 0.5598(3) 0.0326(8) Uani 1 1 d . . . O3 O -0.3519(7) 0.7422(2) 0.4554(3) 0.0424(10) Uani 1 1 d . . . C1 C 0.3188(8) 0.6558(3) 0.6600(3) 0.0204(9) Uani 1 1 d . . . C2 C 0.3894(9) 0.7354(3) 0.6856(4) 0.0286(11) Uani 1 1 d . . . H2 H 0.3135 0.7823 0.6549 0.034 Uiso 1 1 calc R . . C3 C 0.5755(9) 0.7434(3) 0.7579(4) 0.0334(12) Uani 1 1 d . . . H3 H 0.6307 0.7971 0.7768 0.040 Uiso 1 1 calc R . . C4 C 0.6828(8) 0.6747(3) 0.8032(4) 0.0296(11) Uani 1 1 d . . . H4 H 0.8094 0.6813 0.8534 0.036 Uiso 1 1 calc R . . C5 C 0.6058(8) 0.5966(3) 0.7755(4) 0.0236(9) Uani 1 1 d . . . H5 H 0.6789 0.5496 0.8074 0.028 Uiso 1 1 calc R . . C6 C 0.4232(7) 0.5857(3) 0.7018(3) 0.0182(8) Uani 1 1 d . . . C7 C 0.3280(8) 0.5014(3) 0.6678(3) 0.0209(9) Uani 1 1 d . . . C8 C 0.1805(9) 0.4660(3) 0.7455(4) 0.0316(11) Uani 1 1 d . . . H8A H 0.0563 0.5051 0.7574 0.047 Uiso 1 1 calc R . . H8B H 0.2775 0.4563 0.8088 0.047 Uiso 1 1 calc R . . H8C H 0.1121 0.4135 0.7207 0.047 Uiso 1 1 calc R . . C9 C 0.5217(9) 0.4430(3) 0.6450(4) 0.0312(11) Uani 1 1 d . . . H9A H 0.4550 0.3900 0.6209 0.047 Uiso 1 1 calc R . . H9B H 0.6251 0.4338 0.7066 0.047 Uiso 1 1 calc R . . H9C H 0.6102 0.4673 0.5929 0.047 Uiso 1 1 calc R . . C10 C -0.2130(9) 0.7833(3) 0.5073(4) 0.0265(10) Uani 1 1 d . . . C11 C -0.2533(11) 0.8774(3) 0.5157(4) 0.0344(12) Uani 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 I1 0.02263(19) 0.01680(18) 0.02089(18) -0.00064(10) -0.00541(12) 0.00176(10) F1 0.214(7) 0.029(2) 0.088(4) -0.002(2) 0.080(4) 0.022(3) F2 0.089(4) 0.035(2) 0.145(5) -0.007(3) 0.016(3) -0.012(2) F3 0.175(6) 0.027(2) 0.102(4) -0.003(2) -0.085(4) 0.022(3) O1 0.0308(18) 0.0168(15) 0.0244(16) -0.0021(13) -0.0110(13) 0.0040(13) O2 0.037(2) 0.0192(17) 0.039(2) -0.0008(14) -0.0141(16) 0.0057(15) O3 0.048(2) 0.0249(19) 0.049(2) -0.0112(17) -0.0254(19) 0.0072(17) C1 0.018(2) 0.022(2) 0.020(2) -0.0019(18) -0.0019(16) -0.0002(17) C2 0.029(3) 0.019(2) 0.036(3) -0.001(2) -0.008(2) -0.0002(19) C3 0.035(3) 0.021(2) 0.042(3) -0.007(2) -0.008(2) -0.003(2) C4 0.024(2) 0.030(3) 0.033(3) -0.007(2) -0.010(2) -0.003(2) C5 0.022(2) 0.023(2) 0.025(2) 0.0019(19) -0.0044(18) 0.0046(18) C6 0.020(2) 0.018(2) 0.016(2) -0.0021(16) 0.0015(16) -0.0015(17) C7 0.020(2) 0.019(2) 0.021(2) -0.0020(18) -0.0067(17) -0.0018(17) C8 0.035(3) 0.029(3) 0.030(3) 0.007(2) -0.004(2) -0.010(2) C9 0.033(3) 0.021(2) 0.037(3) -0.009(2) -0.009(2) 0.007(2) C10 0.033(3) 0.021(2) 0.024(2) 0.0013(18) -0.006(2) 0.0056(19) C11 0.051(3) 0.022(3) 0.027(3) -0.004(2) -0.014(2) 0.006(2) _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 O1 2.011(3) . ? I1 C1 2.094(4) . ? I1 O2 2.233(3) . ? F1 C11 1.265(7) . ? F2 C11 1.354(8) . ? F3 C11 1.261(7) . ? O1 C7 1.442(5) . ? O2 C10 1.268(6) . ? O3 C10 1.208(6) . ? C1 C6 1.375(6) . ? C1 C2 1.382(7) . ? C2 C3 1.381(7) . ? C2 H2 0.9500 . ? C3 C4 1.383(7) . ? C3 H3 0.9500 . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 C6 1.383(6) . ? C5 H5 0.9500 . ? C6 C7 1.523(6) . ? C7 C8 1.509(7) . ? C7 C9 1.515(7) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.544(7) . ? 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 I1 C1 81.08(16) . . ? O1 I1 O2 163.74(13) . . ? C1 I1 O2 82.81(15) . . ? C7 O1 I1 114.6(3) . . ? C10 O2 I1 114.6(3) . . ? C6 C1 C2 123.9(4) . . ? C6 C1 I1 110.8(3) . . ? C2 C1 I1 125.4(3) . . ? C3 C2 C1 116.9(4) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.8(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 117.4(4) . . ? C1 C6 C7 118.9(4) . . ? C5 C6 C7 123.7(4) . . ? O1 C7 C8 109.4(4) . . ? O1 C7 C9 105.7(4) . . ? C8 C7 C9 111.9(4) . . ? O1 C7 C6 108.0(4) . . ? C8 C7 C6 110.3(4) . . ? C9 C7 C6 111.3(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 O2 129.1(5) . . ? O3 C10 C11 119.1(4) . . ? O2 C10 C11 111.8(4) . . ? F3 C11 F1 116.4(6) . . ? F3 C11 F2 101.0(6) . . ? F1 C11 F2 100.5(5) . . ? F3 C11 C10 113.5(4) . . ? F1 C11 C10 112.5(5) . . ? F2 C11 C10 111.4(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 C1 I1 O1 C7 23.0(3) . . . . ? O2 I1 O1 C7 30.7(7) . . . . ? O1 I1 O2 C10 176.3(5) . . . . ? C1 I1 O2 C10 -176.1(4) . . . . ? O1 I1 C1 C6 -12.0(3) . . . . ? O2 I1 C1 C6 170.2(3) . . . . ? O1 I1 C1 C2 168.2(4) . . . . ? O2 I1 C1 C2 -9.6(4) . . . . ? C6 C1 C2 C3 -0.3(8) . . . . ? I1 C1 C2 C3 179.5(4) . . . . ? C1 C2 C3 C4 -0.9(8) . . . . ? C2 C3 C4 C5 0.7(8) . . . . ? C3 C4 C5 C6 0.7(8) . . . . ? C2 C1 C6 C5 1.6(7) . . . . ? I1 C1 C6 C5 -178.2(3) . . . . ? C2 C1 C6 C7 179.6(5) . . . . ? I1 C1 C6 C7 -0.2(5) . . . . ? C4 C5 C6 C1 -1.8(7) . . . . ? C4 C5 C6 C7 -179.6(4) . . . . ? I1 O1 C7 C8 92.3(4) . . . . ? I1 O1 C7 C9 -147.0(3) . . . . ? I1 O1 C7 C6 -27.8(4) . . . . ? C1 C6 C7 O1 17.9(5) . . . . ? C5 C6 C7 O1 -164.3(4) . . . . ? C1 C6 C7 C8 -101.7(5) . . . . ? C5 C6 C7 C8 76.1(6) . . . . ? C1 C6 C7 C9 133.4(4) . . . . ? C5 C6 C7 C9 -48.8(6) . . . . ? I1 O2 C10 O3 -0.1(8) . . . . ? I1 O2 C10 C11 179.3(3) . . . . ? O3 C10 C11 F3 -26.7(9) . . . . ? O2 C10 C11 F3 153.9(6) . . . . ? O3 C10 C11 F1 108.1(7) . . . . ? O2 C10 C11 F1 -71.3(7) . . . . ? O3 C10 C11 F2 -140.0(6) . . . . ? O2 C10 C11 F2 40.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.449 _refine_diff_density_min -0.860 _refine_diff_density_rms 0.158 _database_code_depnum_ccdc_archive 'CCDC 946860' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12094 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 I O4 S' _chemical_formula_sum 'C16 H17 I O4 S' _chemical_formula_weight 432.26 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' S S 0.1246 0.1234 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2948(18) _cell_length_b 10.663(2) _cell_length_c 18.336(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.233(4) _cell_angle_gamma 90.00 _cell_volume 1590.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 933 _cell_measurement_theta_min 3.690 _cell_measurement_theta_max 28.117 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 2.159 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details ; absorption correction based on 8571 reflections(SADABS);Rint 0.0863 before correction and 0.0263 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker Apex 2000 CCD area detector' _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 12066 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3127 _reflns_number_gt 2901 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0334P)^2^+0.0953P] 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 3127 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0608 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.149827(19) -0.055794(15) 0.128208(9) 0.01675(7) Uani 1 1 d . . . S1 S 0.24118(8) 0.14237(6) 0.00019(4) 0.01799(15) Uani 1 1 d . . . O1 O 0.0616(2) -0.17711(18) 0.19232(10) 0.0233(4) Uani 1 1 d . . . O2 O 0.3171(2) 0.07279(17) 0.06894(11) 0.0245(4) Uani 1 1 d . . . O3 O 0.1944(2) 0.05619(16) -0.06185(11) 0.0233(4) Uani 1 1 d . . . O4 O 0.1106(2) 0.22422(18) 0.01254(12) 0.0278(5) Uani 1 1 d . . . C1 C 0.3751(3) -0.1144(2) 0.19235(15) 0.0173(5) Uani 1 1 d . . . C2 C 0.5289(3) -0.0938(3) 0.17655(16) 0.0208(6) Uani 1 1 d . . . H2 H 0.5430 -0.0452 0.1348 0.025 Uiso 1 1 calc R . . C3 C 0.6614(3) -0.1467(3) 0.22382(16) 0.0236(6) Uani 1 1 d . . . H3 H 0.7693 -0.1357 0.2145 0.028 Uiso 1 1 calc R . . C4 C 0.6375(3) -0.2160(3) 0.28504(16) 0.0258(6) Uani 1 1 d . . . H4 H 0.7296 -0.2514 0.3175 0.031 Uiso 1 1 calc R . . C5 C 0.4816(3) -0.2342(3) 0.29935(16) 0.0243(6) Uani 1 1 d . . . H5 H 0.4673 -0.2820 0.3414 0.029 Uiso 1 1 calc R . . C6 C 0.3456(3) -0.1829(2) 0.25247(15) 0.0193(6) Uani 1 1 d . . . C7 C 0.1694(3) -0.1937(3) 0.26404(16) 0.0232(6) Uani 1 1 d . . . C8 C 0.1338(4) -0.0924(3) 0.31780(17) 0.0281(7) Uani 1 1 d . . . H8A H 0.1581 -0.0097 0.2993 0.042 Uiso 1 1 calc R . . H8B H 0.2028 -0.1065 0.3669 0.042 Uiso 1 1 calc R . . H8C H 0.0177 -0.0962 0.3217 0.042 Uiso 1 1 calc R . . C9 C 0.1288(4) -0.3231(3) 0.28992(17) 0.0295(7) Uani 1 1 d . . . H9A H 0.0102 -0.3292 0.2882 0.044 Uiso 1 1 calc R . . H9B H 0.1879 -0.3367 0.3410 0.044 Uiso 1 1 calc R . . H9C H 0.1620 -0.3868 0.2573 0.044 Uiso 1 1 calc R . . C10 C 0.4046(3) 0.2359(2) -0.01849(14) 0.0180(5) Uani 1 1 d . . . C11 C 0.5663(3) 0.2009(2) 0.00773(15) 0.0198(6) Uani 1 1 d . . . H11 H 0.5907 0.1289 0.0384 0.024 Uiso 1 1 calc R . . C12 C 0.6926(3) 0.2718(3) -0.01101(15) 0.0216(6) Uani 1 1 d . . . H12 H 0.8035 0.2487 0.0077 0.026 Uiso 1 1 calc R . . C13 C 0.6588(3) 0.3759(3) -0.05675(16) 0.0249(6) Uani 1 1 d . . . C14 C 0.4946(4) 0.4088(3) -0.08290(19) 0.0304(7) Uani 1 1 d . . . H14 H 0.4694 0.4798 -0.1143 0.037 Uiso 1 1 calc R . . C15 C 0.3687(3) 0.3398(3) -0.06384(17) 0.0264(6) Uani 1 1 d . . . H15 H 0.2576 0.3635 -0.0818 0.032 Uiso 1 1 calc R . . C16 C 0.7966(4) 0.4511(3) -0.0780(2) 0.0366(8) Uani 1 1 d . . . H16A H 0.8040 0.5327 -0.0531 0.055 Uiso 1 1 calc R . . H16B H 0.7747 0.4635 -0.1320 0.055 Uiso 1 1 calc R . . H16C H 0.9005 0.4057 -0.0628 0.055 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 0.01274(11) 0.02163(12) 0.01547(11) 0.00067(6) 0.00171(7) 0.00048(6) S1 0.0136(3) 0.0214(3) 0.0183(3) 0.0014(3) 0.0014(3) 0.0000(2) O1 0.0154(9) 0.0306(11) 0.0230(10) 0.0067(9) 0.0014(8) -0.0049(8) O2 0.0189(10) 0.0311(11) 0.0215(11) 0.0072(8) -0.0008(8) -0.0046(8) O3 0.0196(10) 0.0261(11) 0.0223(11) -0.0035(8) -0.0004(9) -0.0041(7) O4 0.0179(10) 0.0289(11) 0.0374(12) -0.0020(9) 0.0074(9) 0.0019(8) C1 0.0132(12) 0.0176(13) 0.0198(14) -0.0017(11) -0.0002(11) 0.0007(10) C2 0.0194(14) 0.0237(14) 0.0203(14) -0.0001(12) 0.0063(12) -0.0003(11) C3 0.0136(13) 0.0295(15) 0.0272(15) 0.0010(12) 0.0029(12) 0.0003(11) C4 0.0184(14) 0.0305(16) 0.0272(16) 0.0052(12) 0.0009(12) 0.0042(12) C5 0.0234(15) 0.0264(15) 0.0230(15) 0.0068(12) 0.0041(12) 0.0017(12) C6 0.0170(13) 0.0210(14) 0.0202(14) -0.0002(11) 0.0043(11) -0.0001(11) C7 0.0163(13) 0.0314(15) 0.0215(14) 0.0078(12) 0.0028(11) 0.0002(11) C8 0.0223(15) 0.0368(17) 0.0255(16) 0.0016(13) 0.0051(13) 0.0021(13) C9 0.0234(15) 0.0300(16) 0.0355(17) 0.0065(13) 0.0067(13) -0.0051(12) C10 0.0159(13) 0.0202(13) 0.0176(13) -0.0024(11) 0.0028(11) -0.0019(10) C11 0.0200(13) 0.0220(14) 0.0176(14) -0.0020(11) 0.0040(11) 0.0028(11) C12 0.0154(13) 0.0294(15) 0.0198(14) -0.0060(12) 0.0028(11) 0.0036(11) C13 0.0225(15) 0.0260(15) 0.0281(16) -0.0030(12) 0.0093(13) -0.0023(12) C14 0.0265(16) 0.0249(15) 0.0401(19) 0.0105(14) 0.0070(14) -0.0003(12) C15 0.0207(15) 0.0248(15) 0.0334(16) 0.0048(13) 0.0044(13) 0.0040(11) C16 0.0312(18) 0.0312(18) 0.051(2) 0.0031(15) 0.0157(17) -0.0061(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 I1 O1 1.9815(18) . ? I1 C1 2.100(3) . ? I1 O2 2.3607(19) . ? S1 O4 1.4426(19) . ? S1 O3 1.455(2) . ? S1 O2 1.492(2) . ? S1 C10 1.769(3) . ? O1 C7 1.450(3) . ? C1 C2 1.379(4) . ? C1 C6 1.383(4) . ? C2 C3 1.381(4) . ? C2 H2 0.9500 . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.382(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.522(3) . ? C7 C9 1.518(4) . ? C7 C8 1.529(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.382(4) . ? C10 C11 1.385(4) . ? C11 C12 1.388(4) . ? C11 H11 0.9500 . ? C12 C13 1.387(4) . ? C12 H12 0.9500 . ? C13 C14 1.398(4) . ? C13 C16 1.508(4) . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 I1 C1 82.23(9) . . ? O1 I1 O2 166.03(7) . . ? C1 I1 O2 83.80(9) . . ? O4 S1 O3 114.27(12) . . ? O4 S1 O2 111.98(12) . . ? O3 S1 O2 110.53(11) . . ? O4 S1 C10 108.44(12) . . ? O3 S1 C10 107.58(12) . . ? O2 S1 C10 103.34(12) . . ? C7 O1 I1 112.57(15) . . ? S1 O2 I1 119.25(11) . . ? C2 C1 C6 124.4(2) . . ? C2 C1 I1 126.4(2) . . ? C6 C1 I1 109.11(18) . . ? C1 C2 C3 117.3(3) . . ? C1 C2 H2 121.3 . . ? C3 C2 H2 121.3 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 116.9(2) . . ? C1 C6 C7 118.3(2) . . ? C5 C6 C7 124.7(2) . . ? O1 C7 C9 105.0(2) . . ? O1 C7 C6 107.7(2) . . ? C9 C7 C6 113.0(2) . . ? O1 C7 C8 109.6(2) . . ? C9 C7 C8 111.0(2) . . ? C6 C7 C8 110.3(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 120.3(2) . . ? C15 C10 S1 119.0(2) . . ? C11 C10 S1 120.5(2) . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 118.5(3) . . ? C12 C13 C16 120.5(3) . . ? C14 C13 C16 121.0(3) . . ? C15 C14 C13 121.0(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 119.7(3) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C1 I1 O1 C7 26.78(17) . . . . ? O2 I1 O1 C7 27.3(4) . . . . ? O4 S1 O2 I1 57.88(15) . . . . ? O3 S1 O2 I1 -70.76(15) . . . . ? C10 S1 O2 I1 174.39(12) . . . . ? O1 I1 O2 S1 170.5(2) . . . . ? C1 I1 O2 S1 171.05(14) . . . . ? O1 I1 C1 C2 165.5(2) . . . . ? O2 I1 C1 C2 -14.3(2) . . . . ? O1 I1 C1 C6 -11.85(18) . . . . ? O2 I1 C1 C6 168.28(19) . . . . ? C6 C1 C2 C3 0.7(4) . . . . ? I1 C1 C2 C3 -176.3(2) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? I1 C1 C6 C5 177.1(2) . . . . ? C2 C1 C6 C7 178.0(3) . . . . ? I1 C1 C6 C7 -4.6(3) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C4 C5 C6 C7 -178.1(3) . . . . ? I1 O1 C7 C9 -155.17(17) . . . . ? I1 O1 C7 C6 -34.5(3) . . . . ? I1 O1 C7 C8 85.5(2) . . . . ? C1 C6 C7 O1 25.3(3) . . . . ? C5 C6 C7 O1 -156.5(3) . . . . ? C1 C6 C7 C9 140.8(3) . . . . ? C5 C6 C7 C9 -41.0(4) . . . . ? C1 C6 C7 C8 -94.3(3) . . . . ? C5 C6 C7 C8 83.8(3) . . . . ? O4 S1 C10 C15 -41.2(3) . . . . ? O3 S1 C10 C15 82.8(2) . . . . ? O2 S1 C10 C15 -160.2(2) . . . . ? O4 S1 C10 C11 143.1(2) . . . . ? O3 S1 C10 C11 -92.8(2) . . . . ? O2 S1 C10 C11 24.1(2) . . . . ? C15 C10 C11 C12 0.8(4) . . . . ? S1 C10 C11 C12 176.43(19) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C11 C12 C13 C16 -178.9(3) . . . . ? C12 C13 C14 C15 0.1(5) . . . . ? C16 C13 C14 C15 179.6(3) . . . . ? C13 C14 C15 C10 -0.4(5) . . . . ? C11 C10 C15 C14 -0.1(4) . . . . ? S1 C10 C15 C14 -175.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.705 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 946861'