# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name H.Ibrahim S.Murray data_has22 _database_code_depnum_ccdc_archive 'CCDC 874275' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 I O3' _chemical_formula_sum 'C16 H19 I O3' _chemical_formula_weight 386.21 _chemical_absolute_configuration ad 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' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.6625(2) _cell_length_b 13.8534(3) _cell_length_c 11.4816(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1377.85(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8675 _cell_measurement_theta_min 7.7110 _cell_measurement_theta_max 76.6641 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1873 _exptl_crystal_size_mid 0.1514 _exptl_crystal_size_min 0.0115 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.862 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 18.308 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.110 _exptl_absorpt_correction_T_max 0.803 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _exptl_special_details ; Hydrogen atoms of the water molecule were located in the difference fourier map. Their isotropic thermal displacement parameters were fixed to 1.5 times the equivalent one of O3. O-H bond distances were restrained to be 0.84 \%A using DFIX. They refined to 0.83(2) \%A and 0.84(2) \%A. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12015 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 7.72 _diffrn_reflns_theta_max 76.87 _reflns_number_total 2570 _reflns_number_gt 2449 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0476P)^2^+0.4093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _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 -0.009(8) _refine_ls_number_reflns 2570 _refine_ls_number_parameters 187 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.067 _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 I I 0.108497(19) 0.947035(12) 0.67137(4) 0.01433(9) Uani 1 1 d . . . C1 C 0.0504(4) 0.8020(3) 0.6344(3) 0.0161(7) Uani 1 1 d . . . C2 C 0.1395(4) 0.7274(3) 0.6797(6) 0.0172(7) Uani 1 1 d . . . C3 C 0.2838(4) 0.7239(3) 0.7530(4) 0.0210(8) Uani 1 1 d . . . H3 H 0.3522 0.7819 0.7490 0.025 Uiso 1 1 calc R . . C4 C 0.2330(5) 0.6917(3) 0.8769(4) 0.0239(8) Uani 1 1 d . . . H4A H 0.3204 0.6951 0.9323 0.029 Uiso 1 1 calc R . . H4B H 0.1477 0.7326 0.9062 0.029 Uiso 1 1 calc R . . C5 C 0.1789(5) 0.5863(3) 0.8596(4) 0.0233(8) Uani 1 1 d . . . H5A H 0.0687 0.5787 0.8805 0.028 Uiso 1 1 calc R . . H5B H 0.2413 0.5411 0.9070 0.028 Uiso 1 1 calc R . . C6 C 0.2050(5) 0.5688(3) 0.7266(4) 0.0191(8) Uani 1 1 d . . . H6 H 0.2092 0.4997 0.7013 0.023 Uiso 1 1 calc R . . C7 C 0.0908(4) 0.6316(3) 0.6635(6) 0.0166(8) Uani 1 1 d . . . C8 C 0.3542(4) 0.6281(3) 0.7079(4) 0.0207(8) Uani 1 1 d . . . H8A H 0.3855 0.6315 0.6251 0.025 Uiso 1 1 calc R . . H8B H 0.4412 0.6051 0.7564 0.025 Uiso 1 1 calc R . . C9 C -0.0455(5) 0.6091(3) 0.6042(3) 0.0197(8) Uani 1 1 d . . . H9 H -0.0767 0.5441 0.5929 0.024 Uiso 1 1 calc R . . C10 C -0.1334(4) 0.6850(3) 0.5626(4) 0.0164(7) Uani 1 1 d . . . C11 C -0.2851(5) 0.6883(3) 0.4974(4) 0.0197(9) Uani 1 1 d . . . H11 H -0.3540 0.6312 0.5086 0.024 Uiso 1 1 calc R . . C12 C -0.2489(6) 0.7145(3) 0.3701(4) 0.0220(9) Uani 1 1 d . . . H12A H -0.3427 0.7106 0.3211 0.026 Uiso 1 1 calc R . . H12B H -0.1689 0.6712 0.3374 0.026 Uiso 1 1 calc R . . C13 C -0.1890(5) 0.8202(3) 0.3783(4) 0.0204(8) Uani 1 1 d . . . H13A H -0.0806 0.8251 0.3517 0.025 Uiso 1 1 calc R . . H13B H -0.2538 0.8645 0.3315 0.025 Uiso 1 1 calc R . . C14 C -0.2029(4) 0.8427(3) 0.5104(4) 0.0176(7) Uani 1 1 d . . . H14 H -0.2038 0.9128 0.5314 0.021 Uiso 1 1 calc R . . C15 C -0.3505(5) 0.7862(3) 0.5414(4) 0.0198(8) Uani 1 1 d . . . H15A H -0.4420 0.8079 0.4969 0.024 Uiso 1 1 calc R . . H15B H -0.3731 0.7861 0.6259 0.024 Uiso 1 1 calc R . . C16 C -0.0852(4) 0.7818(3) 0.5735(3) 0.0148(7) Uani 1 1 d . . . O1 O 0.3163(3) 0.94578(17) 0.6642(5) 0.0221(6) Uani 1 1 d . . . O2 O 0.0795(4) 0.9376(2) 0.8283(3) 0.0222(6) Uani 1 1 d . . . O3 O 0.1277(4) 0.9435(2) 0.4444(4) 0.0221(7) Uani 1 1 d D . . H1O3 H 0.214(4) 0.943(3) 0.412(5) 0.033 Uiso 1 1 d D . . H2O3 H 0.072(6) 0.977(4) 0.399(5) 0.033 Uiso 1 1 d 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 I 0.01269(12) 0.01704(13) 0.01327(12) -0.00053(18) -0.00084(15) -0.00075(6) C1 0.0169(17) 0.0175(18) 0.0140(16) -0.0012(12) 0.0017(13) -0.0035(14) C2 0.0151(14) 0.0223(16) 0.0141(17) 0.003(2) 0.002(2) 0.0006(11) C3 0.0177(18) 0.027(2) 0.0185(17) 0.0009(16) -0.0030(15) -0.0008(14) C4 0.027(2) 0.031(2) 0.0142(17) 0.0003(17) 0.0001(16) 0.0038(16) C5 0.025(2) 0.026(2) 0.0197(19) 0.0019(16) 0.0029(16) 0.0044(16) C6 0.0197(18) 0.0165(19) 0.021(2) 0.0032(16) 0.0023(16) 0.0000(14) C7 0.0136(14) 0.0244(17) 0.012(2) 0.001(2) 0.0044(19) 0.0000(11) C8 0.0150(17) 0.025(2) 0.022(2) 0.0006(15) 0.0020(14) 0.0003(15) C9 0.021(2) 0.022(2) 0.016(2) -0.0029(14) 0.0037(15) 0.0012(15) C10 0.0157(17) 0.020(2) 0.0137(18) -0.0005(15) -0.0001(14) -0.0043(14) C11 0.0168(19) 0.023(2) 0.020(2) -0.0008(18) -0.0013(15) -0.0025(15) C12 0.026(2) 0.024(2) 0.0164(19) -0.0031(17) -0.0034(18) -0.0060(16) C13 0.0199(19) 0.025(2) 0.017(2) 0.0002(16) -0.0058(16) 0.0002(15) C14 0.0164(17) 0.0212(19) 0.0151(18) -0.0038(14) -0.0011(14) 0.0028(14) C15 0.0143(17) 0.026(2) 0.019(2) -0.0032(16) 0.0020(16) -0.0009(14) C16 0.0181(18) 0.016(2) 0.0105(17) -0.0027(14) -0.0005(13) -0.0014(13) O1 0.0171(11) 0.0267(13) 0.0226(17) 0.0027(15) -0.0029(19) -0.0016(8) O2 0.0222(14) 0.0300(18) 0.0144(17) -0.0011(11) -0.0011(13) -0.0020(11) O3 0.0181(14) 0.0292(18) 0.0190(19) 0.0051(11) 0.0018(13) -0.0002(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 I O1 1.802(3) . ? I O2 1.824(4) . ? I C1 2.114(4) . ? I O3 2.612(4) . ? I O1 2.936(3) 3_475 ? C1 C2 1.391(6) . ? C1 C16 1.396(6) . ? C2 C7 1.405(5) . ? C2 C3 1.507(6) . ? C3 C8 1.550(6) . ? C3 C4 1.554(6) . ? C3 H3 1.0000 . ? C4 C5 1.547(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.562(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.504(6) . ? C6 C8 1.546(5) . ? C6 H6 1.0000 . ? C7 C9 1.398(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.383(6) . ? C9 H9 0.9500 . ? C10 C16 1.410(6) . ? C10 C11 1.513(6) . ? C11 C12 1.538(7) . ? C11 C15 1.553(6) . ? C11 H11 1.0000 . ? C12 C13 1.556(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.553(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C16 1.509(5) . ? C14 C15 1.542(5) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? O3 H1O3 0.83(2) . ? O3 H2O3 0.85(2) . ? 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 I O2 100.5(2) . . ? O1 I C1 102.67(13) . . ? O2 I C1 95.58(15) . . ? O1 I O3 83.7(2) . . ? O2 I O3 173.27(13) . . ? C1 I O3 78.29(13) . . ? O1 I O1 149.87(6) . 3_475 ? O2 I O1 86.87(16) . 3_475 ? C1 I O1 105.66(12) . 3_475 ? O3 I O1 92.09(14) . 3_475 ? C2 C1 C16 120.4(3) . . ? C2 C1 I 120.0(3) . . ? C16 C1 I 119.4(3) . . ? C1 C2 C7 119.1(4) . . ? C1 C2 C3 133.8(4) . . ? C7 C2 C3 107.1(4) . . ? C2 C3 C8 99.6(3) . . ? C2 C3 C4 106.6(4) . . ? C8 C3 C4 99.9(3) . . ? C2 C3 H3 116.1 . . ? C8 C3 H3 116.1 . . ? C4 C3 H3 116.1 . . ? C5 C4 C3 103.8(4) . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C4 C5 C6 103.2(3) . . ? C4 C5 H5A 111.1 . . ? C6 C5 H5A 111.1 . . ? C4 C5 H5B 111.1 . . ? C6 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? C7 C6 C8 100.1(3) . . ? C7 C6 C5 106.6(4) . . ? C8 C6 C5 100.0(3) . . ? C7 C6 H6 115.9 . . ? C8 C6 H6 115.9 . . ? C5 C6 H6 115.9 . . ? C9 C7 C2 121.9(4) . . ? C9 C7 C6 131.4(4) . . ? C2 C7 C6 106.5(4) . . ? C6 C8 C3 94.6(3) . . ? C6 C8 H8A 112.8 . . ? C3 C8 H8A 112.8 . . ? C6 C8 H8B 112.8 . . ? C3 C8 H8B 112.8 . . ? H8A C8 H8B 110.3 . . ? C10 C9 C7 117.7(4) . . ? C10 C9 H9 121.2 . . ? C7 C9 H9 121.2 . . ? C9 C10 C16 122.0(4) . . ? C9 C10 C11 132.2(4) . . ? C16 C10 C11 105.8(3) . . ? C10 C11 C12 107.4(4) . . ? C10 C11 C15 100.5(3) . . ? C12 C11 C15 100.2(3) . . ? C10 C11 H11 115.5 . . ? C12 C11 H11 115.5 . . ? C15 C11 H11 115.5 . . ? C11 C12 C13 103.4(3) . . ? C11 C12 H12A 111.1 . . ? C13 C12 H12A 111.1 . . ? C11 C12 H12B 111.1 . . ? C13 C12 H12B 111.1 . . ? H12A C12 H12B 109.0 . . ? C14 C13 C12 102.9(4) . . ? C14 C13 H13A 111.2 . . ? C12 C13 H13A 111.2 . . ? C14 C13 H13B 111.2 . . ? C12 C13 H13B 111.2 . . ? H13A C13 H13B 109.1 . . ? C16 C14 C15 99.5(3) . . ? C16 C14 C13 107.7(3) . . ? C15 C14 C13 100.8(3) . . ? C16 C14 H14 115.6 . . ? C15 C14 H14 115.6 . . ? C13 C14 H14 115.6 . . ? C14 C15 C11 93.8(3) . . ? C14 C15 H15A 113.0 . . ? C11 C15 H15A 113.0 . . ? C14 C15 H15B 113.0 . . ? C11 C15 H15B 113.0 . . ? H15A C15 H15B 110.4 . . ? C1 C16 C10 118.9(4) . . ? C1 C16 C14 134.2(4) . . ? C10 C16 C14 106.8(3) . . ? I O3 H1O3 120(5) . . ? I O3 H2O3 125(4) . . ? H1O3 O3 H2O3 104(6) . . ? 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 O1 I C1 C2 39.4(4) . . . . ? O2 I C1 C2 -62.7(4) . . . . ? O3 I C1 C2 120.1(4) . . . . ? O1 I C1 C2 -151.0(4) 3_475 . . . ? O1 I C1 C16 -146.5(3) . . . . ? O2 I C1 C16 111.4(3) . . . . ? O3 I C1 C16 -65.8(3) . . . . ? O1 I C1 C16 23.1(3) 3_475 . . . ? C16 C1 C2 C7 -0.1(7) . . . . ? I C1 C2 C7 174.0(4) . . . . ? C16 C1 C2 C3 -176.4(5) . . . . ? I C1 C2 C3 -2.3(8) . . . . ? C1 C2 C3 C8 -149.7(6) . . . . ? C7 C2 C3 C8 33.7(5) . . . . ? C1 C2 C3 C4 106.9(6) . . . . ? C7 C2 C3 C4 -69.7(5) . . . . ? C2 C3 C4 C5 67.2(4) . . . . ? C8 C3 C4 C5 -36.0(4) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C4 C5 C6 C7 -67.9(4) . . . . ? C4 C5 C6 C8 35.9(4) . . . . ? C1 C2 C7 C9 -0.7(8) . . . . ? C3 C2 C7 C9 176.5(5) . . . . ? C1 C2 C7 C6 -177.2(5) . . . . ? C3 C2 C7 C6 -0.1(6) . . . . ? C8 C6 C7 C9 150.2(6) . . . . ? C5 C6 C7 C9 -106.1(6) . . . . ? C8 C6 C7 C2 -33.8(5) . . . . ? C5 C6 C7 C2 70.0(5) . . . . ? C7 C6 C8 C3 51.7(4) . . . . ? C5 C6 C8 C3 -57.3(4) . . . . ? C2 C3 C8 C6 -51.5(4) . . . . ? C4 C3 C8 C6 57.4(4) . . . . ? C2 C7 C9 C10 -0.8(8) . . . . ? C6 C7 C9 C10 174.8(5) . . . . ? C7 C9 C10 C16 3.1(7) . . . . ? C7 C9 C10 C11 -179.0(5) . . . . ? C9 C10 C11 C12 -106.0(5) . . . . ? C16 C10 C11 C12 72.2(4) . . . . ? C9 C10 C11 C15 149.7(5) . . . . ? C16 C10 C11 C15 -32.2(4) . . . . ? C10 C11 C12 C13 -67.1(4) . . . . ? C15 C11 C12 C13 37.4(4) . . . . ? C11 C12 C13 C14 -1.6(4) . . . . ? C12 C13 C14 C16 68.5(4) . . . . ? C12 C13 C14 C15 -35.2(4) . . . . ? C16 C14 C15 C11 -53.2(3) . . . . ? C13 C14 C15 C11 57.0(3) . . . . ? C10 C11 C15 C14 52.1(4) . . . . ? C12 C11 C15 C14 -58.0(3) . . . . ? C2 C1 C16 C10 2.3(6) . . . . ? I C1 C16 C10 -171.8(3) . . . . ? C2 C1 C16 C14 -177.1(5) . . . . ? I C1 C16 C14 8.8(6) . . . . ? C9 C10 C16 C1 -3.9(6) . . . . ? C11 C10 C16 C1 177.7(4) . . . . ? C9 C10 C16 C14 175.6(4) . . . . ? C11 C10 C16 C14 -2.7(4) . . . . ? C15 C14 C16 C1 -143.7(5) . . . . ? C13 C14 C16 C1 111.6(5) . . . . ? C15 C14 C16 C10 36.8(4) . . . . ? C13 C14 C16 C10 -67.9(4) . . . . ? 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 O3 H1O3 O2 0.83(2) 2.03(2) 2.866(5) 177(6) 4_554 O3 H2O3 O2 0.85(2) 1.95(2) 2.777(5) 166(6) 2_574 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.044 _refine_diff_density_min -1.022 _refine_diff_density_rms 0.102 # Attachment '- 11.cif' data_has21 _database_code_depnum_ccdc_archive 'CCDC 874276' #TrackingRef '- 11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 I, C7 H7 O3 S, 2 (C H Cl3)' _chemical_formula_sum 'C31 H31 O3 S Cl6 I' _chemical_formula_weight 823.22 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.4318(9) _cell_length_b 11.7919(9) _cell_length_c 13.3530(10) _cell_angle_alpha 80.086(2) _cell_angle_beta 76.784(2) _cell_angle_gamma 89.133(2) _cell_volume 1725.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5420 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 24.66 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.484 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5529 _exptl_absorpt_correction_T_max 0.7080 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.047 before and 0.020 after correction. The Ratio of minimum to maximum transmission is 0.780998. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13766 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.86 _reflns_number_total 5891 _reflns_number_gt 5321 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0466P)^2^+2.1430P] 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 5891 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _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 I I 0.30028(2) 0.622664(19) 0.463200(18) 0.02909(9) Uani 1 1 d . . . C1 C 0.2924(3) 0.7804(3) 0.3639(3) 0.0279(8) Uani 1 1 d . . . C2 C 0.2884(4) 0.8818(3) 0.4020(3) 0.0422(10) Uani 1 1 d . . . C3 C 0.2852(8) 0.9106(4) 0.5085(4) 0.087(2) Uani 1 1 d . . . H3 H 0.3196 0.8509 0.5557 0.104 Uiso 1 1 calc R . . C4 C 0.1638(11) 0.9406(7) 0.5505(6) 0.140(4) Uani 1 1 d . . . H4A H 0.1521 0.9505 0.6242 0.169 Uiso 1 1 calc R . . H4B H 0.1055 0.8816 0.5457 0.169 Uiso 1 1 calc R . . C5 C 0.1517(10) 1.0533(5) 0.4807(5) 0.138(4) Uani 1 1 d . . . H5A H 0.1316 1.1157 0.5223 0.166 Uiso 1 1 calc R . . H5B H 0.0879 1.0468 0.4427 0.166 Uiso 1 1 calc R . . C6 C 0.2775(7) 1.0784(4) 0.4021(4) 0.084(2) Uani 1 1 d . . . H6 H 0.2945 1.1595 0.3645 0.101 Uiso 1 1 calc R . . C7 C 0.2851(4) 0.9860(3) 0.3345(3) 0.0448(10) Uani 1 1 d . . . C8 C 0.3610(10) 1.0303(6) 0.4713(6) 0.145(4) Uani 1 1 d . . . H8A H 0.3603 1.0733 0.5288 0.174 Uiso 1 1 calc R . . H8B H 0.4443 1.0217 0.4319 0.174 Uiso 1 1 calc R . . C9 C 0.2857(5) 0.9888(4) 0.2312(4) 0.0561(13) Uani 1 1 d . . . H9 H 0.2820 1.0597 0.1860 0.067 Uiso 1 1 calc R . . C10 C 0.2917(5) 0.8868(4) 0.1953(3) 0.0472(11) Uani 1 1 d . . . C11 C 0.2983(6) 0.8614(4) 0.0873(4) 0.0669(15) Uani 1 1 d . . . H11 H 0.2677 0.9227 0.0387 0.080 Uiso 1 1 calc R . . C12 C 0.4249(6) 0.8296(5) 0.0513(4) 0.0744(16) Uani 1 1 d . . . H12A H 0.4808 0.8871 0.0622 0.089 Uiso 1 1 calc R . . H12B H 0.4431 0.8236 -0.0237 0.089 Uiso 1 1 calc R . . C13 C 0.4346(5) 0.7142(4) 0.1177(3) 0.0542(12) Uani 1 1 d . . . H13A H 0.4973 0.7172 0.1576 0.065 Uiso 1 1 calc R . . H13B H 0.4547 0.6539 0.0738 0.065 Uiso 1 1 calc R . . C14 C 0.3096(4) 0.6900(4) 0.1920(3) 0.0451(10) Uani 1 1 d . . . H14 H 0.2897 0.6086 0.2278 0.054 Uiso 1 1 calc R . . C15 C 0.2961(3) 0.7810(3) 0.2605(3) 0.0322(8) Uani 1 1 d . . . C16 C 0.2319(5) 0.7441(5) 0.1119(5) 0.0745(18) Uani 1 1 d . . . H16A H 0.2425 0.7052 0.0505 0.089 Uiso 1 1 calc R . . H16B H 0.1455 0.7481 0.1451 0.089 Uiso 1 1 calc R . . C17 C 0.1197(3) 0.6207(3) 0.5476(3) 0.0307(8) Uani 1 1 d . . . C18 C 0.0287(3) 0.6451(3) 0.4957(3) 0.0356(9) Uani 1 1 d . . . H18 H 0.0461 0.6632 0.4216 0.043 Uiso 1 1 calc R . . C19 C -0.0877(4) 0.6427(3) 0.5532(4) 0.0411(10) Uani 1 1 d . . . H19 H -0.1516 0.6599 0.5188 0.049 Uiso 1 1 calc R . . C20 C -0.1117(4) 0.6155(4) 0.6600(4) 0.0495(11) Uani 1 1 d . . . H20 H -0.1924 0.6138 0.6994 0.059 Uiso 1 1 calc R . . C21 C -0.0195(4) 0.5906(4) 0.7106(4) 0.0565(13) Uani 1 1 d . . . H21 H -0.0370 0.5723 0.7847 0.068 Uiso 1 1 calc R . . C22 C 0.0982(4) 0.5921(4) 0.6542(3) 0.0444(10) Uani 1 1 d . . . H22 H 0.1622 0.5739 0.6883 0.053 Uiso 1 1 calc R . . O1 O 0.7017(2) 0.6041(2) 0.42925(19) 0.0362(6) Uani 1 1 d . . . O2 O 0.6911(3) 0.5688(2) 0.2603(2) 0.0416(7) Uani 1 1 d . . . O3 O 0.5315(2) 0.6687(3) 0.3577(3) 0.0539(8) Uani 1 1 d . . . S S 0.65739(8) 0.64412(7) 0.33633(7) 0.0281(2) Uani 1 1 d . . . C23 C 0.7327(3) 0.7770(3) 0.2781(3) 0.0280(8) Uani 1 1 d . . . C24 C 0.6684(4) 0.8706(3) 0.2441(3) 0.0357(9) Uani 1 1 d . . . H24 H 0.5835 0.8647 0.2549 0.043 Uiso 1 1 calc R . . C25 C 0.7291(4) 0.9726(3) 0.1945(3) 0.0470(11) Uani 1 1 d . . . H25 H 0.6852 1.0368 0.1708 0.056 Uiso 1 1 calc R . . C26 C 0.8502(5) 0.9829(4) 0.1791(4) 0.0534(12) Uani 1 1 d . . . C29 C 0.9169(6) 1.0951(5) 0.1243(5) 0.085(2) Uani 1 1 d . . . H29A H 0.9678 1.0840 0.0571 0.127 Uiso 1 1 calc R . . H29B H 0.9671 1.1186 0.1680 0.127 Uiso 1 1 calc R . . H29C H 0.8587 1.1549 0.1125 0.127 Uiso 1 1 calc R . . C27 C 0.9138(4) 0.8891(4) 0.2149(4) 0.0539(12) Uani 1 1 d . . . H27 H 0.9985 0.8961 0.2057 0.065 Uiso 1 1 calc R . . C28 C 0.8550(4) 0.7857(3) 0.2638(3) 0.0411(10) Uani 1 1 d . . . H28 H 0.8989 0.7214 0.2872 0.049 Uiso 1 1 calc R . . C30 C 0.5379(3) 0.3730(3) 0.2415(3) 0.0331(8) Uani 1 1 d . . . H30 H 0.5800 0.4501 0.2218 0.040 Uiso 1 1 calc R . . Cl1 Cl 0.44353(10) 0.36559(11) 0.15577(8) 0.0489(3) Uani 1 1 d . . . Cl2 Cl 0.64709(11) 0.26661(11) 0.22962(10) 0.0589(3) Uani 1 1 d . . . Cl3 Cl 0.45432(9) 0.35956(8) 0.37033(7) 0.0375(2) Uani 1 1 d . . . C31 C 0.8105(4) 0.6472(4) 0.0366(3) 0.0406(9) Uani 1 1 d . . . H31 H 0.7727 0.6434 0.1125 0.049 Uiso 1 1 calc R . . Cl4 Cl 0.96580(10) 0.64371(10) 0.02251(10) 0.0540(3) Uani 1 1 d . . . Cl5 Cl 0.75697(11) 0.52757(10) -0.00375(10) 0.0549(3) Uani 1 1 d . . . Cl6 Cl 0.76732(12) 0.77456(11) -0.03075(12) 0.0703(4) 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 I 0.03282(14) 0.02265(14) 0.03154(15) 0.00336(9) -0.01285(10) 0.00105(9) C1 0.0311(19) 0.0195(17) 0.034(2) 0.0015(15) -0.0134(16) 0.0033(14) C2 0.067(3) 0.026(2) 0.037(2) -0.0026(17) -0.021(2) -0.0010(19) C3 0.193(8) 0.037(3) 0.042(3) -0.014(2) -0.048(4) 0.014(4) C4 0.274(13) 0.074(5) 0.069(5) -0.021(4) -0.027(6) 0.053(7) C5 0.292(13) 0.045(4) 0.059(4) -0.013(3) 0.000(6) 0.028(5) C6 0.183(7) 0.023(2) 0.059(4) -0.009(2) -0.054(4) 0.007(3) C7 0.071(3) 0.025(2) 0.041(2) -0.0022(18) -0.022(2) 0.0018(19) C8 0.302(13) 0.074(5) 0.126(7) -0.055(5) -0.158(8) 0.037(6) C9 0.099(4) 0.024(2) 0.049(3) 0.0061(19) -0.033(3) -0.003(2) C10 0.082(3) 0.032(2) 0.030(2) 0.0017(17) -0.022(2) -0.005(2) C11 0.115(5) 0.046(3) 0.039(3) -0.001(2) -0.021(3) 0.009(3) C12 0.112(5) 0.062(3) 0.052(3) -0.004(3) -0.027(3) 0.002(3) C13 0.075(3) 0.050(3) 0.033(2) -0.008(2) -0.002(2) 0.012(2) C14 0.062(3) 0.032(2) 0.039(2) -0.0104(18) -0.004(2) 0.000(2) C15 0.036(2) 0.030(2) 0.029(2) -0.0032(16) -0.0063(16) -0.0019(16) C16 0.072(4) 0.093(4) 0.089(4) -0.065(4) -0.044(3) 0.018(3) C17 0.035(2) 0.0215(18) 0.035(2) -0.0053(15) -0.0069(16) 0.0017(15) C18 0.041(2) 0.028(2) 0.041(2) -0.0047(17) -0.0161(18) -0.0015(16) C19 0.036(2) 0.031(2) 0.062(3) -0.013(2) -0.017(2) 0.0018(17) C20 0.039(2) 0.039(2) 0.063(3) -0.006(2) 0.001(2) 0.0045(19) C21 0.052(3) 0.070(3) 0.038(3) -0.001(2) 0.001(2) 0.018(2) C22 0.045(2) 0.049(3) 0.037(2) -0.004(2) -0.0113(19) 0.011(2) O1 0.0508(17) 0.0302(14) 0.0268(14) 0.0024(11) -0.0128(12) 0.0028(12) O2 0.0601(18) 0.0326(15) 0.0323(15) -0.0036(12) -0.0115(13) -0.0142(13) O3 0.0286(15) 0.0497(18) 0.070(2) 0.0196(16) -0.0067(14) -0.0021(13) S 0.0298(5) 0.0251(5) 0.0272(5) 0.0038(4) -0.0081(4) -0.0010(4) C23 0.036(2) 0.0255(19) 0.0220(18) -0.0041(14) -0.0045(15) -0.0023(15) C24 0.044(2) 0.028(2) 0.033(2) -0.0027(16) -0.0069(17) 0.0031(17) C25 0.071(3) 0.024(2) 0.042(2) -0.0037(18) -0.007(2) 0.003(2) C26 0.075(3) 0.027(2) 0.050(3) -0.009(2) 0.007(2) -0.009(2) C29 0.102(5) 0.042(3) 0.090(4) -0.011(3) 0.022(4) -0.031(3) C27 0.039(2) 0.051(3) 0.065(3) -0.019(2) 0.008(2) -0.014(2) C28 0.037(2) 0.033(2) 0.051(3) -0.0113(19) -0.0024(19) 0.0010(17) C30 0.036(2) 0.033(2) 0.032(2) -0.0105(16) -0.0097(17) 0.0024(16) Cl1 0.0434(6) 0.0743(8) 0.0354(6) -0.0189(5) -0.0152(5) -0.0001(5) Cl2 0.0626(7) 0.0630(8) 0.0544(7) -0.0203(6) -0.0147(6) 0.0313(6) Cl3 0.0421(5) 0.0421(5) 0.0294(5) -0.0103(4) -0.0072(4) -0.0033(4) C31 0.041(2) 0.042(2) 0.037(2) -0.0023(18) -0.0079(18) -0.0047(18) Cl4 0.0430(6) 0.0422(6) 0.0784(8) -0.0008(6) -0.0237(6) -0.0043(5) Cl5 0.0515(7) 0.0549(7) 0.0618(7) -0.0092(6) -0.0196(6) -0.0123(5) Cl6 0.0595(8) 0.0535(7) 0.0937(10) 0.0115(7) -0.0273(7) 0.0077(6) _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 I C1 2.104(3) . ? I C17 2.112(4) . ? I O3 2.709(3) . ? I O1 2.807(2) 2_666 ? C1 C15 1.370(5) . ? C1 C2 1.374(5) . ? C2 C7 1.399(5) . ? C2 C3 1.510(6) . ? C3 C4 1.437(12) . ? C3 C8 1.609(11) . ? C3 H3 1.0000 . ? C4 C5 1.510(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.572(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.514(9) . ? C6 C7 1.519(6) . ? C6 H6 1.0000 . ? C7 C9 1.373(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.365(6) . ? C9 H9 0.9500 . ? C10 C15 1.400(5) . ? C10 C11 1.507(6) . ? C11 C12 1.481(8) . ? C11 C16 1.536(8) . ? C11 H11 1.0000 . ? C12 C13 1.507(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.541(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.510(5) . ? C14 C16 1.588(7) . ? C14 H14 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.370(6) . ? C17 C18 1.377(5) . ? C18 C19 1.374(6) . ? C18 H18 0.9500 . ? C19 C20 1.370(6) . ? C19 H19 0.9500 . ? C20 C21 1.380(7) . ? C20 H20 0.9500 . ? C21 C22 1.382(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? O1 S 1.448(3) . ? O2 S 1.445(3) . ? O3 S 1.437(3) . ? S C23 1.766(4) . ? C23 C28 1.369(5) . ? C23 C24 1.386(5) . ? C24 C25 1.382(6) . ? C24 H24 0.9500 . ? C25 C26 1.357(7) . ? C25 H25 0.9500 . ? C26 C27 1.390(7) . ? C26 C29 1.519(6) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C27 C28 1.385(6) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C30 Cl3 1.748(4) . ? C30 Cl1 1.756(4) . ? C30 Cl2 1.757(4) . ? C30 H30 1.0000 . ? C31 Cl6 1.739(4) . ? C31 Cl4 1.743(4) . ? C31 Cl5 1.759(4) . ? C31 H31 1.0000 . ? 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 C1 I C17 95.69(14) . . ? C1 I O3 76.15(11) . . ? C17 I O3 168.97(12) . . ? C1 I O1 170.55(11) . 2_666 ? C17 I O1 84.17(11) . 2_666 ? O3 I O1 105.11(8) . 2_666 ? C15 C1 C2 120.6(3) . . ? C15 C1 I 119.4(3) . . ? C2 C1 I 119.9(3) . . ? C1 C2 C7 119.2(4) . . ? C1 C2 C3 133.8(4) . . ? C7 C2 C3 107.1(4) . . ? C4 C3 C2 106.7(6) . . ? C4 C3 C8 105.8(6) . . ? C2 C3 C8 98.2(4) . . ? C4 C3 H3 114.8 . . ? C2 C3 H3 114.8 . . ? C8 C3 H3 114.8 . . ? C3 C4 C5 102.2(7) . . ? C3 C4 H4A 111.3 . . ? C5 C4 H4A 111.3 . . ? C3 C4 H4B 111.3 . . ? C5 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? C4 C5 C6 105.7(7) . . ? C4 C5 H5A 110.6 . . ? C6 C5 H5A 110.6 . . ? C4 C5 H5B 110.6 . . ? C6 C5 H5B 110.6 . . ? H5A C5 H5B 108.7 . . ? C8 C6 C7 100.3(4) . . ? C8 C6 C5 100.9(6) . . ? C7 C6 C5 103.6(5) . . ? C8 C6 H6 116.5 . . ? C7 C6 H6 116.5 . . ? C5 C6 H6 116.5 . . ? C9 C7 C2 121.3(4) . . ? C9 C7 C6 133.4(4) . . ? C2 C7 C6 105.2(4) . . ? C6 C8 C3 91.7(6) . . ? C6 C8 H8A 113.3 . . ? C3 C8 H8A 113.3 . . ? C6 C8 H8B 113.3 . . ? C3 C8 H8B 113.3 . . ? H8A C8 H8B 110.7 . . ? C10 C9 C7 118.1(4) . . ? C10 C9 H9 120.9 . . ? C7 C9 H9 120.9 . . ? C9 C10 C15 122.1(4) . . ? C9 C10 C11 130.9(4) . . ? C15 C10 C11 107.0(4) . . ? C12 C11 C10 104.0(5) . . ? C12 C11 C16 102.1(4) . . ? C10 C11 C16 101.6(4) . . ? C12 C11 H11 115.7 . . ? C10 C11 H11 115.7 . . ? C16 C11 H11 115.7 . . ? C11 C12 C13 104.3(5) . . ? C11 C12 H12A 110.9 . . ? C13 C12 H12A 110.9 . . ? C11 C12 H12B 110.9 . . ? C13 C12 H12B 110.9 . . ? H12A C12 H12B 108.9 . . ? C12 C13 C14 104.9(4) . . ? C12 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? C12 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? H13A C13 H13B 108.8 . . ? C15 C14 C13 105.0(4) . . ? C15 C14 C16 100.0(3) . . ? C13 C14 C16 97.7(4) . . ? C15 C14 H14 117.0 . . ? C13 C14 H14 117.0 . . ? C16 C14 H14 117.0 . . ? C1 C15 C10 118.7(3) . . ? C1 C15 C14 134.7(4) . . ? C10 C15 C14 106.6(3) . . ? C11 C16 C14 93.2(4) . . ? C11 C16 H16A 113.1 . . ? C14 C16 H16A 113.1 . . ? C11 C16 H16B 113.1 . . ? C14 C16 H16B 113.1 . . ? H16A C16 H16B 110.4 . . ? C22 C17 C18 122.5(4) . . ? C22 C17 I 117.2(3) . . ? C18 C17 I 120.3(3) . . ? C19 C18 C17 118.7(4) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.4(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 117.9(4) . . ? C17 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? S O3 I 152.61(17) . . ? O3 S O2 113.1(2) . . ? O3 S O1 113.67(18) . . ? O2 S O1 111.62(16) . . ? O3 S C23 105.74(17) . . ? O2 S C23 105.80(16) . . ? O1 S C23 106.12(16) . . ? C28 C23 C24 120.5(3) . . ? C28 C23 S 119.6(3) . . ? C24 C23 S 119.8(3) . . ? C25 C24 C23 119.3(4) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C26 C25 C24 121.2(4) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.2(4) . . ? C25 C26 C29 121.1(5) . . ? C27 C26 C29 119.7(5) . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C27 C26 120.6(4) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C23 C28 C27 119.3(4) . . ? C23 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? Cl3 C30 Cl1 110.8(2) . . ? Cl3 C30 Cl2 110.8(2) . . ? Cl1 C30 Cl2 110.4(2) . . ? Cl3 C30 H30 108.2 . . ? Cl1 C30 H30 108.2 . . ? Cl2 C30 H30 108.2 . . ? Cl6 C31 Cl4 111.6(2) . . ? Cl6 C31 Cl5 110.5(2) . . ? Cl4 C31 Cl5 111.2(2) . . ? Cl6 C31 H31 107.8 . . ? Cl4 C31 H31 107.8 . . ? Cl5 C31 H31 107.8 . . ? 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 C17 I C1 C15 -109.4(3) . . . . ? O3 I C1 C15 78.1(3) . . . . ? O1 I C1 C15 -20.7(9) 2_666 . . . ? C17 I C1 C2 73.2(3) . . . . ? O3 I C1 C2 -99.3(3) . . . . ? O1 I C1 C2 161.9(5) 2_666 . . . ? C15 C1 C2 C7 1.6(6) . . . . ? I C1 C2 C7 179.0(3) . . . . ? C15 C1 C2 C3 -179.2(6) . . . . ? I C1 C2 C3 -1.8(8) . . . . ? C1 C2 C3 C4 -104.1(7) . . . . ? C7 C2 C3 C4 75.2(6) . . . . ? C1 C2 C3 C8 146.5(6) . . . . ? C7 C2 C3 C8 -34.2(7) . . . . ? C2 C3 C4 C5 -68.7(7) . . . . ? C8 C3 C4 C5 35.2(7) . . . . ? C3 C4 C5 C6 -1.2(8) . . . . ? C4 C5 C6 C8 -34.9(7) . . . . ? C4 C5 C6 C7 68.7(7) . . . . ? C1 C2 C7 C9 0.0(7) . . . . ? C3 C2 C7 C9 -179.4(5) . . . . ? C1 C2 C7 C6 178.4(5) . . . . ? C3 C2 C7 C6 -1.0(6) . . . . ? C8 C6 C7 C9 -143.2(7) . . . . ? C5 C6 C7 C9 112.8(7) . . . . ? C8 C6 C7 C2 38.7(7) . . . . ? C5 C6 C7 C2 -65.3(6) . . . . ? C7 C6 C8 C3 -55.7(6) . . . . ? C5 C6 C8 C3 50.4(5) . . . . ? C4 C3 C8 C6 -55.7(7) . . . . ? C2 C3 C8 C6 54.3(6) . . . . ? C2 C7 C9 C10 -1.1(8) . . . . ? C6 C7 C9 C10 -178.9(6) . . . . ? C7 C9 C10 C15 0.6(8) . . . . ? C7 C9 C10 C11 -177.6(5) . . . . ? C9 C10 C11 C12 105.7(7) . . . . ? C15 C10 C11 C12 -72.8(5) . . . . ? C9 C10 C11 C16 -148.5(6) . . . . ? C15 C10 C11 C16 33.0(5) . . . . ? C10 C11 C12 C13 70.0(5) . . . . ? C16 C11 C12 C13 -35.4(5) . . . . ? C11 C12 C13 C14 -2.0(5) . . . . ? C12 C13 C14 C15 -65.8(5) . . . . ? C12 C13 C14 C16 36.8(5) . . . . ? C2 C1 C15 C10 -2.1(6) . . . . ? I C1 C15 C10 -179.5(3) . . . . ? C2 C1 C15 C14 174.8(4) . . . . ? I C1 C15 C14 -2.6(6) . . . . ? C9 C10 C15 C1 0.9(7) . . . . ? C11 C10 C15 C1 179.5(4) . . . . ? C9 C10 C15 C14 -176.7(5) . . . . ? C11 C10 C15 C14 1.9(5) . . . . ? C13 C14 C15 C1 -110.9(5) . . . . ? C16 C14 C15 C1 148.3(5) . . . . ? C13 C14 C15 C10 66.2(4) . . . . ? C16 C14 C15 C10 -34.6(5) . . . . ? C12 C11 C16 C14 56.7(4) . . . . ? C10 C11 C16 C14 -50.5(5) . . . . ? C15 C14 C16 C11 51.3(4) . . . . ? C13 C14 C16 C11 -55.5(4) . . . . ? C1 I C17 C22 -134.6(3) . . . . ? O3 I C17 C22 -92.9(7) . . . . ? O1 I C17 C22 54.9(3) 2_666 . . . ? C1 I C17 C18 46.8(3) . . . . ? O3 I C17 C18 88.5(7) . . . . ? O1 I C17 C18 -123.7(3) 2_666 . . . ? C22 C17 C18 C19 1.3(6) . . . . ? I C17 C18 C19 179.8(3) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? C18 C19 C20 C21 0.2(6) . . . . ? C19 C20 C21 C22 -0.4(7) . . . . ? C18 C17 C22 C21 -1.5(6) . . . . ? I C17 C22 C21 179.9(3) . . . . ? C20 C21 C22 C17 1.0(7) . . . . ? C1 I O3 S 176.0(5) . . . . ? C17 I O3 S 133.0(6) . . . . ? O1 I O3 S -13.7(5) 2_666 . . . ? I O3 S O2 88.4(5) . . . . ? I O3 S O1 -40.3(5) . . . . ? I O3 S C23 -156.3(4) . . . . ? O3 S C23 C28 169.5(3) . . . . ? O2 S C23 C28 -70.2(3) . . . . ? O1 S C23 C28 48.5(3) . . . . ? O3 S C23 C24 -12.5(4) . . . . ? O2 S C23 C24 107.7(3) . . . . ? O1 S C23 C24 -133.6(3) . . . . ? C28 C23 C24 C25 0.7(6) . . . . ? S C23 C24 C25 -177.2(3) . . . . ? C23 C24 C25 C26 -0.4(6) . . . . ? C24 C25 C26 C27 -0.7(7) . . . . ? C24 C25 C26 C29 179.9(4) . . . . ? C25 C26 C27 C28 1.3(7) . . . . ? C29 C26 C27 C28 -179.2(5) . . . . ? C24 C23 C28 C27 -0.1(6) . . . . ? S C23 C28 C27 177.9(3) . . . . ? C26 C27 C28 C23 -1.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.86 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.107 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.086 # Attachment '- 12f.cif' data_has24 _database_code_depnum_ccdc_archive 'CCDC 874277' #TrackingRef '- 12f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 I, F6 P' _chemical_formula_sum 'C22 H22 F6 I P' _chemical_formula_weight 558.27 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.5505(2) _cell_length_b 12.8539(2) _cell_length_c 18.8604(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.496(2) _cell_angle_gamma 90.00 _cell_volume 2069.04(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15392 _cell_measurement_theta_min 3.4356 _cell_measurement_theta_max 76.6729 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1118 _exptl_crystal_size_mid 0.0419 _exptl_crystal_size_min 0.0285 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 13.448 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.330 _exptl_absorpt_correction_T_max 0.749 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3196 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22762 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 70.00 _reflns_number_total 3918 _reflns_number_gt 3541 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^)+(0.0872P)^2^+0.8215P] 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 3918 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C1 C 0.3910(4) 0.7650(3) 0.06571(19) 0.0217(7) Uani 1 1 d . . . C2 C 0.5438(5) 0.7317(3) 0.0823(2) 0.0256(8) Uani 1 1 d . . . C3 C 0.6304(5) 0.6310(3) 0.0724(3) 0.0315(9) Uani 1 1 d . . . H3 H 0.5853 0.5843 0.0340 0.038 Uiso 1 1 calc R . . C4 C 0.6548(5) 0.5812(4) 0.1471(3) 0.0362(10) Uani 1 1 d . . . H4A H 0.5548 0.5773 0.1708 0.043 Uiso 1 1 calc R . . H4B H 0.6995 0.5104 0.1442 0.043 Uiso 1 1 calc R . . C5 C 0.7704(6) 0.6553(4) 0.1869(3) 0.0380(11) Uani 1 1 d . . . H5A H 0.8684 0.6188 0.2024 0.046 Uiso 1 1 calc R . . H5B H 0.7237 0.6858 0.2289 0.046 Uiso 1 1 calc R . . C6 C 0.8014(5) 0.7403(4) 0.1311(3) 0.0362(10) Uani 1 1 d . . . H6 H 0.8975 0.7836 0.1409 0.043 Uiso 1 1 calc R . . C7 C 0.6490(5) 0.7992(3) 0.1198(2) 0.0295(9) Uani 1 1 d . . . C8 C 0.7970(6) 0.6730(3) 0.0619(3) 0.0361(11) Uani 1 1 d . . . H8A H 0.8027 0.7153 0.0183 0.043 Uiso 1 1 calc R . . H8B H 0.8777 0.6177 0.0635 0.043 Uiso 1 1 calc R . . C9 C 0.6022(5) 0.8976(3) 0.1416(2) 0.0312(9) Uani 1 1 d . . . H9 H 0.6736 0.9427 0.1670 0.037 Uiso 1 1 calc R . . C10 C 0.4484(5) 0.9273(3) 0.1253(2) 0.0301(9) Uani 1 1 d . . . C11 C 0.3630(6) 1.0273(4) 0.1389(3) 0.0422(11) Uani 1 1 d . . . H11 H 0.4087 1.0708 0.1789 0.051 Uiso 1 1 calc R . . C12 C 0.3416(7) 1.0820(4) 0.0668(3) 0.0474(13) Uani 1 1 d . . . H12A H 0.2991 1.1530 0.0721 0.057 Uiso 1 1 calc R . . H12B H 0.4422 1.0864 0.0436 0.057 Uiso 1 1 calc R . . C13 C 0.2259(6) 1.0131(4) 0.0246(3) 0.0451(12) Uani 1 1 d . . . H13A H 0.2719 0.9863 -0.0187 0.054 Uiso 1 1 calc R . . H13B H 0.1287 1.0519 0.0106 0.054 Uiso 1 1 calc R . . C14 C 0.1916(5) 0.9222(4) 0.0766(3) 0.0385(11) Uani 1 1 d . . . H14 H 0.0948 0.8804 0.0649 0.046 Uiso 1 1 calc R . . C15 C 0.3420(5) 0.8626(3) 0.0873(2) 0.0292(9) Uani 1 1 d . . . C16 C 0.1968(7) 0.9848(4) 0.1480(3) 0.0506(14) Uani 1 1 d . . . H16A H 0.1164 1.0401 0.1483 0.061 Uiso 1 1 calc R . . H16B H 0.1910 0.9395 0.1903 0.061 Uiso 1 1 calc R . . I I 0.23357(3) 0.669057(19) 0.004602(13) 0.02607(13) Uani 1 1 d . . . C17 C 0.2726(5) 0.7299(3) -0.0968(2) 0.0245(8) Uani 1 1 d . . . C18 C 0.4032(5) 0.6953(3) -0.1302(3) 0.0322(9) Uani 1 1 d . . . H18 H 0.4767 0.6494 -0.1068 0.039 Uiso 1 1 calc R . . C19 C 0.4226(6) 0.7297(4) -0.1986(3) 0.0393(10) Uani 1 1 d . . . H19 H 0.5107 0.7075 -0.2231 0.047 Uiso 1 1 calc R . . C20 C 0.3137(6) 0.7966(4) -0.2315(2) 0.0368(10) Uani 1 1 d . . . H20 H 0.3264 0.8189 -0.2788 0.044 Uiso 1 1 calc R . . C21 C 0.1866(6) 0.8312(4) -0.1959(3) 0.0400(12) Uani 1 1 d . . . H21 H 0.1146 0.8787 -0.2185 0.048 Uiso 1 1 calc R . . C22 C 0.1638(5) 0.7974(4) -0.1283(3) 0.0351(10) Uani 1 1 d . . . H22 H 0.0757 0.8197 -0.1040 0.042 Uiso 1 1 calc R . . P P 0.15852(14) 0.44203(8) 0.14435(6) 0.0315(3) Uani 1 1 d . . . F1 F 0.1475(3) 0.5675(2) 0.14154(15) 0.0384(6) Uani 1 1 d . . . F2 F 0.1739(4) 0.3187(2) 0.1452(2) 0.0541(9) Uani 1 1 d . . . F3 F 0.2818(4) 0.4471(2) 0.08374(16) 0.0445(7) Uani 1 1 d . . . F4 F 0.3036(4) 0.4515(3) 0.20233(18) 0.0583(9) Uani 1 1 d . . . F5 F 0.0415(4) 0.4403(3) 0.2054(2) 0.0632(10) Uani 1 1 d . . . F6 F 0.0184(3) 0.4363(2) 0.08457(19) 0.0513(8) 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 C1 0.0189(17) 0.0279(18) 0.0178(18) -0.0011(14) -0.0034(14) -0.0046(14) C2 0.0223(19) 0.0267(19) 0.027(2) 0.0035(15) -0.0025(15) -0.0003(15) C3 0.025(2) 0.030(2) 0.040(2) -0.0012(18) -0.0027(17) 0.0051(17) C4 0.030(2) 0.037(2) 0.042(3) 0.0078(19) 0.0029(19) 0.0060(18) C5 0.035(3) 0.043(2) 0.036(3) 0.0039(19) -0.001(2) 0.0041(19) C6 0.030(2) 0.037(2) 0.040(3) 0.0054(19) -0.0096(19) -0.0018(18) C7 0.027(2) 0.032(2) 0.028(2) 0.0017(17) -0.0049(17) 0.0013(17) C8 0.027(2) 0.046(3) 0.036(3) 0.0047(19) 0.0083(19) 0.0123(18) C9 0.036(2) 0.029(2) 0.027(2) 0.0012(16) -0.0030(17) -0.0041(17) C10 0.037(2) 0.0277(19) 0.027(2) -0.0029(16) 0.0067(17) 0.0017(17) C11 0.047(3) 0.033(2) 0.047(3) -0.010(2) 0.008(2) 0.006(2) C12 0.047(3) 0.033(2) 0.062(4) 0.005(2) 0.010(3) 0.010(2) C13 0.041(3) 0.045(3) 0.050(3) 0.022(2) 0.004(2) 0.012(2) C14 0.028(2) 0.037(2) 0.052(3) 0.006(2) 0.010(2) 0.0049(18) C15 0.025(2) 0.0292(19) 0.035(2) 0.0014(18) 0.0073(17) 0.0021(17) C16 0.049(3) 0.053(3) 0.051(3) 0.008(2) 0.022(2) 0.024(2) I 0.02240(18) 0.03000(19) 0.02535(19) 0.00262(8) -0.00238(11) -0.00417(8) C17 0.0252(19) 0.0291(18) 0.0188(18) 0.0025(14) -0.0030(15) -0.0008(15) C18 0.028(2) 0.0286(19) 0.040(2) 0.0000(18) 0.0025(18) 0.0026(17) C19 0.039(2) 0.040(2) 0.040(3) -0.0022(19) 0.012(2) 0.001(2) C20 0.042(3) 0.044(2) 0.025(2) 0.0042(19) 0.0005(18) -0.009(2) C21 0.033(3) 0.044(3) 0.042(3) 0.012(2) -0.004(2) 0.0046(18) C22 0.028(2) 0.042(2) 0.036(2) 0.007(2) -0.0002(18) 0.0086(19) P 0.0333(6) 0.0317(5) 0.0295(6) 0.0006(4) 0.0023(5) 0.0046(4) F1 0.0447(16) 0.0339(13) 0.0356(15) -0.0037(11) -0.0053(12) 0.0032(11) F2 0.057(2) 0.0340(14) 0.072(2) 0.0071(14) 0.0124(18) 0.0104(13) F3 0.0481(17) 0.0449(15) 0.0414(16) 0.0047(12) 0.0104(13) 0.0120(13) F4 0.064(2) 0.065(2) 0.0434(18) 0.0036(15) -0.0194(16) 0.0156(16) F5 0.074(2) 0.0533(18) 0.067(2) 0.0116(16) 0.042(2) 0.0127(16) F6 0.0395(16) 0.0427(15) 0.069(2) -0.0150(14) -0.0207(15) 0.0033(12) _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 C15 1.391(6) . ? C1 C2 1.392(5) . ? C1 I 2.115(4) . ? C2 C7 1.408(6) . ? C2 C3 1.508(6) . ? C3 C8 1.547(6) . ? C3 C4 1.550(6) . ? C3 H3 1.0000 . ? C4 C5 1.535(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.551(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.511(6) . ? C6 C8 1.565(7) . ? C6 H6 1.0000 . ? C7 C9 1.396(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.387(6) . ? C9 H9 0.9500 . ? C10 C15 1.398(6) . ? C10 C11 1.508(6) . ? C11 C12 1.531(8) . ? C11 C16 1.542(8) . ? C11 H11 1.0000 . ? C12 C13 1.517(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.565(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.500(6) . ? C14 C16 1.567(8) . ? C14 H14 1.0000 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? I C17 2.112(4) . ? I F6 2.977(3) 3_565 ? I F1 3.025(3) . ? I F3 3.235(3) . ? C17 C22 1.379(6) . ? C17 C18 1.389(6) . ? C18 C19 1.384(7) . ? C18 H18 0.9500 . ? C19 C20 1.386(7) . ? C19 H19 0.9500 . ? C20 C21 1.385(8) . ? C20 H20 0.9500 . ? C21 C22 1.373(7) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? P F5 1.572(3) . ? P F2 1.591(3) . ? P F6 1.596(3) . ? P F3 1.603(3) . ? P F4 1.608(3) . ? P F1 1.616(3) . ? 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 C15 C1 C2 120.4(3) . . ? C15 C1 I 119.5(3) . . ? C2 C1 I 120.0(3) . . ? C1 C2 C7 119.0(4) . . ? C1 C2 C3 134.2(4) . . ? C7 C2 C3 106.7(4) . . ? C2 C3 C8 100.3(3) . . ? C2 C3 C4 106.4(4) . . ? C8 C3 C4 100.8(4) . . ? C2 C3 H3 115.7 . . ? C8 C3 H3 115.7 . . ? C4 C3 H3 115.7 . . ? C5 C4 C3 103.6(4) . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C4 C5 C6 103.8(4) . . ? C4 C5 H5A 111.0 . . ? C6 C5 H5A 111.0 . . ? C4 C5 H5B 111.0 . . ? C6 C5 H5B 111.0 . . ? H5A C5 H5B 109.0 . . ? C7 C6 C5 105.5(4) . . ? C7 C6 C8 100.5(3) . . ? C5 C6 C8 100.4(4) . . ? C7 C6 H6 116.1 . . ? C5 C6 H6 116.1 . . ? C8 C6 H6 116.1 . . ? C9 C7 C2 121.3(4) . . ? C9 C7 C6 132.2(4) . . ? C2 C7 C6 106.3(4) . . ? C3 C8 C6 93.5(4) . . ? C3 C8 H8A 113.0 . . ? C6 C8 H8A 113.0 . . ? C3 C8 H8B 113.0 . . ? C6 C8 H8B 113.0 . . ? H8A C8 H8B 110.4 . . ? C10 C9 C7 118.0(4) . . ? C10 C9 H9 121.0 . . ? C7 C9 H9 121.0 . . ? C9 C10 C15 121.9(4) . . ? C9 C10 C11 131.3(4) . . ? C15 C10 C11 106.7(4) . . ? C10 C11 C12 105.8(4) . . ? C10 C11 C16 100.1(4) . . ? C12 C11 C16 101.6(4) . . ? C10 C11 H11 115.7 . . ? C12 C11 H11 115.7 . . ? C16 C11 H11 115.7 . . ? C13 C12 C11 103.7(4) . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C12 C13 C14 104.3(4) . . ? C12 C13 H13A 110.9 . . ? C14 C13 H13A 110.9 . . ? C12 C13 H13B 110.9 . . ? C14 C13 H13B 110.9 . . ? H13A C13 H13B 108.9 . . ? C15 C14 C13 105.9(4) . . ? C15 C14 C16 99.6(4) . . ? C13 C14 C16 99.2(4) . . ? C15 C14 H14 116.5 . . ? C13 C14 H14 116.5 . . ? C16 C14 H14 116.5 . . ? C1 C15 C10 119.2(4) . . ? C1 C15 C14 133.8(4) . . ? C10 C15 C14 106.9(4) . . ? C11 C16 C14 93.7(4) . . ? C11 C16 H16A 113.0 . . ? C14 C16 H16A 113.0 . . ? C11 C16 H16B 113.0 . . ? C14 C16 H16B 113.0 . . ? H16A C16 H16B 110.4 . . ? C17 I C1 98.46(15) . . ? C17 I F6 78.79(13) . 3_565 ? C1 I F6 171.05(12) . 3_565 ? C17 I F1 173.41(12) . . ? C1 I F1 88.08(11) . . ? F6 I F1 94.62(9) 3_565 . ? C17 I F3 136.22(12) . . ? C1 I F3 101.78(12) . . ? F6 I F3 85.81(8) 3_565 . ? F1 I F3 41.94(7) . . ? C22 C17 C18 123.2(4) . . ? C22 C17 I 118.9(3) . . ? C18 C17 I 117.9(3) . . ? C19 C18 C17 117.7(4) . . ? C19 C18 H18 121.1 . . ? C17 C18 H18 121.1 . . ? C18 C19 C20 120.0(4) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 120.6(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.6(4) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C17 117.9(4) . . ? C21 C22 H22 121.0 . . ? C17 C22 H22 121.0 . . ? F5 P F2 91.96(19) . . ? F5 P F6 91.9(2) . . ? F2 P F6 91.10(19) . . ? F5 P F3 177.8(2) . . ? F2 P F3 89.42(18) . . ? F6 P F3 89.77(18) . . ? F5 P F4 90.1(2) . . ? F2 P F4 90.5(2) . . ? F6 P F4 177.4(2) . . ? F3 P F4 88.18(19) . . ? F5 P F1 90.00(17) . . ? F2 P F1 178.0(2) . . ? F6 P F1 89.03(15) . . ? F3 P F1 88.62(15) . . ? F4 P F1 89.28(17) . . ? P F1 I 116.22(14) . . ? P F3 I 107.08(13) . . ? 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 C15 C1 C2 C7 -1.6(6) . . . . ? I C1 C2 C7 176.6(3) . . . . ? C15 C1 C2 C3 174.7(5) . . . . ? I C1 C2 C3 -7.1(7) . . . . ? C1 C2 C3 C8 147.8(5) . . . . ? C7 C2 C3 C8 -35.5(5) . . . . ? C1 C2 C3 C4 -107.6(5) . . . . ? C7 C2 C3 C4 69.1(4) . . . . ? C2 C3 C4 C5 -67.8(4) . . . . ? C8 C3 C4 C5 36.5(4) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C7 68.3(5) . . . . ? C4 C5 C6 C8 -35.7(4) . . . . ? C1 C2 C7 C9 1.3(6) . . . . ? C3 C2 C7 C9 -175.9(4) . . . . ? C1 C2 C7 C6 178.6(4) . . . . ? C3 C2 C7 C6 1.3(5) . . . . ? C5 C6 C7 C9 105.8(6) . . . . ? C8 C6 C7 C9 -150.3(5) . . . . ? C5 C6 C7 C2 -71.1(5) . . . . ? C8 C6 C7 C2 32.9(5) . . . . ? C2 C3 C8 C6 52.2(4) . . . . ? C4 C3 C8 C6 -56.8(4) . . . . ? C7 C6 C8 C3 -51.5(4) . . . . ? C5 C6 C8 C3 56.6(4) . . . . ? C2 C7 C9 C10 -0.1(7) . . . . ? C6 C7 C9 C10 -176.6(5) . . . . ? C7 C9 C10 C15 -0.8(7) . . . . ? C7 C9 C10 C11 -178.0(5) . . . . ? C9 C10 C11 C12 106.4(6) . . . . ? C15 C10 C11 C12 -71.1(5) . . . . ? C9 C10 C11 C16 -148.3(5) . . . . ? C15 C10 C11 C16 34.2(5) . . . . ? C10 C11 C12 C13 68.4(5) . . . . ? C16 C11 C12 C13 -35.7(5) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C12 C13 C14 C15 -66.8(5) . . . . ? C12 C13 C14 C16 36.0(5) . . . . ? C2 C1 C15 C10 0.7(6) . . . . ? I C1 C15 C10 -177.5(3) . . . . ? C2 C1 C15 C14 177.7(5) . . . . ? I C1 C15 C14 -0.5(7) . . . . ? C9 C10 C15 C1 0.5(7) . . . . ? C11 C10 C15 C1 178.3(4) . . . . ? C9 C10 C15 C14 -177.2(4) . . . . ? C11 C10 C15 C14 0.6(5) . . . . ? C13 C14 C15 C1 -109.2(6) . . . . ? C16 C14 C15 C1 148.3(5) . . . . ? C13 C14 C15 C10 68.1(5) . . . . ? C16 C14 C15 C10 -34.4(5) . . . . ? C10 C11 C16 C14 -51.9(4) . . . . ? C12 C11 C16 C14 56.7(4) . . . . ? C15 C14 C16 C11 52.3(4) . . . . ? C13 C14 C16 C11 -55.8(4) . . . . ? C15 C1 I C17 85.1(3) . . . . ? C2 C1 I C17 -93.1(3) . . . . ? C15 C1 I F1 -94.1(3) . . . . ? C2 C1 I F1 87.7(3) . . . . ? C15 C1 I F3 -134.0(3) . . . . ? C2 C1 I F3 47.8(3) . . . . ? C1 I C17 C22 -102.5(4) . . . . ? F6 I C17 C22 68.9(3) 3_565 . . . ? F3 I C17 C22 140.6(3) . . . . ? C1 I C17 C18 81.0(3) . . . . ? F6 I C17 C18 -107.7(3) 3_565 . . . ? F3 I C17 C18 -36.0(4) . . . . ? C22 C17 C18 C19 -0.8(7) . . . . ? I C17 C18 C19 175.6(3) . . . . ? C17 C18 C19 C20 0.0(7) . . . . ? C18 C19 C20 C21 1.3(7) . . . . ? C19 C20 C21 C22 -2.0(8) . . . . ? C20 C21 C22 C17 1.2(7) . . . . ? C18 C17 C22 C21 0.1(7) . . . . ? I C17 C22 C21 -176.2(4) . . . . ? F5 P F1 I -157.92(19) . . . . ? F6 P F1 I -66.01(18) . . . . ? F3 P F1 I 23.78(17) . . . . ? F4 P F1 I 111.98(18) . . . . ? C1 I F1 P -127.45(18) . . . . ? F6 I F1 P 61.10(15) 3_565 . . . ? F3 I F1 P -17.39(13) . . . . ? F2 P F3 I 159.42(17) . . . . ? F6 P F3 I 68.32(15) . . . . ? F4 P F3 I -110.05(16) . . . . ? F1 P F3 I -20.72(14) . . . . ? C17 I F3 P -154.27(18) . . . . ? C1 I F3 P 89.96(18) . . . . ? F6 I F3 P -85.25(16) 3_565 . . . ? F1 I F3 P 16.43(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.381 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.138