Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Myroslav Vysotsky' _publ_contact_author_address ; Chemie, Pharmazie und Geowissenschaften Johannes Gutenberg - Universitat Duesbergweg 10-14 Mainz 55128 GERMANY ; _publ_contact_author_email VYSOTSKY@UNI-MAINZ.DE _publ_section_title ; OH - pi and halogen - pi interactions as driving forces in the crystal organisations of tri-bromo and tri-iodo trityl alcohols ; loop_ _publ_author_name 'Myroslav Vysotsky' 'Thomas Ruhl' 'Dieter Schollmeyer' 'Oleg V. Shishkin' #data_tr133rent data_1/A _database_code_depnum_ccdc_archive 'CCDC 658146' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 Br3 O' _chemical_formula_sum 'C19 H13 Br3 O' _chemical_formula_weight 497.02 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' Br Br -0.2901 2.4595 '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 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.7670(3) _cell_length_b 10.9110(4) _cell_length_c 18.3190(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1752.3(1) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4462 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.7 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.884 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 6.907 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1 _exptl_absorpt_correction_T_max 0.46 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'SMART CCD' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'CCD scan' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19361 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 30.11 _reflns_number_total 5145 _reflns_number_gt 3256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.0 (Bruker, 2006)' _computing_cell_refinement 'APEX2 V2.0 (Bruker, 2006)' _computing_data_reduction 'APEX2 V2.0 (Bruker, 2006)' _computing_structure_solution 'SIR-97 (Altomare, 1997)' _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^)+(0.0193P)^2^+0.0000P] 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 -0.010(10) _refine_ls_number_reflns 5145 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 0.808 _refine_ls_restrained_S_all 0.808 _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 Br1 Br -0.26418(4) 0.43376(3) 0.765967(19) 0.04264(10) Uani 1 1 d . . . Br2 Br 0.73087(5) 0.73366(3) 0.48956(2) 0.05740(13) Uani 1 1 d . . . Br3 Br 0.73034(4) -0.08404(3) 0.689077(19) 0.04148(10) Uani 1 1 d . . . C1 C 0.2866(4) 0.3094(3) 0.56553(16) 0.0256(7) Uani 1 1 d . . . C2 C 0.1543(4) 0.3407(3) 0.61760(18) 0.0241(8) Uani 1 1 d . . . C3 C 0.1008(3) 0.2556(3) 0.66683(18) 0.0302(8) Uani 1 1 d . . . H3 H 0.1504 0.1785 0.6711 0.036 Uiso 1 1 calc R . . C4 C -0.0250(4) 0.2812(4) 0.71040(19) 0.0323(9) Uani 1 1 d . . . H4 H -0.0615 0.2223 0.7443 0.039 Uiso 1 1 calc R . . C5 C -0.0968(4) 0.3946(3) 0.70364(18) 0.0297(8) Uani 1 1 d . . . C6 C -0.0459(4) 0.4797(3) 0.6546(2) 0.0345(9) Uani 1 1 d . . . H6 H -0.0958 0.5566 0.6501 0.041 Uiso 1 1 calc R . . C7 C 0.0807(4) 0.4519(4) 0.61109(19) 0.0316(9) Uani 1 1 d . . . H7 H 0.1164 0.5104 0.5767 0.038 Uiso 1 1 calc R . . C8 C 0.3852(3) 0.4215(3) 0.54608(18) 0.0251(7) Uani 1 1 d . . . C9 C 0.4362(3) 0.4374(3) 0.47571(19) 0.0295(8) Uani 1 1 d . . . H9 H 0.4028 0.3831 0.4384 0.035 Uiso 1 1 calc R . . C10 C 0.5376(4) 0.5333(3) 0.4583(2) 0.0369(9) Uani 1 1 d . . . H10 H 0.5715 0.5447 0.4095 0.044 Uiso 1 1 calc R . . C11 C 0.5861(4) 0.6090(3) 0.5121(2) 0.0339(9) Uani 1 1 d . . . C12 C 0.5368(4) 0.5962(3) 0.5832(2) 0.0354(9) Uani 1 1 d . . . H12 H 0.5718 0.6506 0.6201 0.042 Uiso 1 1 calc R . . C13 C 0.4355(4) 0.5027(3) 0.6001(2) 0.0314(9) Uani 1 1 d . . . H13 H 0.3999 0.4938 0.6488 0.038 Uiso 1 1 calc R . . C14 C 0.3914(3) 0.2089(3) 0.59676(17) 0.0231(7) Uani 1 1 d . . . C15 C 0.4087(3) 0.0969(3) 0.56135(17) 0.0259(8) Uani 1 1 d . . . H15 H 0.3518 0.0806 0.5183 0.031 Uiso 1 1 calc R . . C16 C 0.5085(4) 0.0085(3) 0.5882(2) 0.0296(8) Uani 1 1 d . . . H16 H 0.5194 -0.0679 0.5639 0.035 Uiso 1 1 calc R . . C17 C 0.5917(4) 0.0333(3) 0.65085(19) 0.0274(8) Uani 1 1 d . . . C18 C 0.5737(4) 0.1429(3) 0.68683(19) 0.0296(8) Uani 1 1 d . . . H18 H 0.6298 0.1587 0.7302 0.036 Uiso 1 1 calc R . . C19 C 0.4738(3) 0.2303(3) 0.65992(19) 0.0288(8) Uani 1 1 d . . . H19 H 0.4618 0.3058 0.6851 0.035 Uiso 1 1 calc R . . O20 O 0.2227(2) 0.25895(18) 0.49968(10) 0.0304(5) Uani 1 1 d . . . H20 H 0.1404 0.2949 0.4899 0.046 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 Br1 0.02778(19) 0.0526(2) 0.0475(2) -0.02063(18) 0.00781(17) -0.00144(19) Br2 0.0489(3) 0.0306(2) 0.0926(3) 0.0008(2) 0.0289(3) -0.0081(2) Br3 0.0404(2) 0.0418(2) 0.04222(19) 0.01138(17) 0.00106(18) 0.0145(2) C1 0.0247(18) 0.0236(17) 0.0285(17) 0.0009(14) 0.0007(15) -0.0004(15) C2 0.0176(18) 0.029(2) 0.0260(18) -0.0052(16) -0.0024(14) 0.0012(14) C3 0.0272(19) 0.030(2) 0.034(2) 0.0009(18) 0.0004(15) -0.0008(16) C4 0.026(2) 0.035(2) 0.035(2) 0.0018(18) 0.0036(15) -0.0055(16) C5 0.0222(18) 0.038(2) 0.0289(19) -0.0147(17) -0.0008(14) -0.0034(16) C6 0.028(2) 0.028(2) 0.047(2) -0.0003(19) -0.0013(18) 0.0051(16) C7 0.030(2) 0.033(2) 0.032(2) 0.0031(18) -0.0003(16) 0.0034(17) C8 0.0188(16) 0.0249(19) 0.0317(18) 0.0024(17) -0.0011(13) 0.0077(15) C9 0.0258(17) 0.029(2) 0.0334(19) 0.0021(17) 0.0018(14) 0.0037(16) C10 0.040(2) 0.030(2) 0.041(2) 0.0077(19) 0.0118(18) 0.0099(17) C11 0.0245(19) 0.0184(19) 0.059(3) 0.0086(19) 0.0099(18) 0.0006(15) C12 0.033(2) 0.026(2) 0.047(2) -0.0027(19) -0.0013(18) 0.0016(16) C13 0.032(2) 0.028(2) 0.034(2) -0.0002(18) 0.0046(16) 0.0001(16) C14 0.0188(17) 0.0242(19) 0.0261(18) 0.0014(16) 0.0040(14) -0.0016(14) C15 0.0227(17) 0.028(2) 0.0265(18) 0.0005(16) 0.0011(14) -0.0052(15) C16 0.032(2) 0.021(2) 0.036(2) -0.0001(18) 0.0082(16) 0.0026(16) C17 0.0243(18) 0.025(2) 0.033(2) 0.0087(17) 0.0046(15) 0.0017(15) C18 0.0254(19) 0.034(2) 0.0295(19) -0.0010(18) -0.0049(16) -0.0027(16) C19 0.028(2) 0.029(2) 0.030(2) -0.0007(18) -0.0025(15) 0.0013(17) O20 0.0272(12) 0.0330(12) 0.0311(11) -0.0053(10) -0.0068(10) 0.0036(11) _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 Br1 C5 1.908(3) . ? Br2 C11 1.905(3) . ? Br3 C17 1.899(3) . ? C1 O20 1.439(3) . ? C1 C8 1.540(4) . ? C1 C2 1.540(4) . ? C1 C14 1.540(4) . ? C2 C3 1.377(4) . ? C2 C7 1.379(5) . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(5) . ? C4 H4 0.9500 . ? C5 C6 1.366(5) . ? C6 C7 1.400(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.375(4) . ? C8 C13 1.400(5) . ? C9 C10 1.410(5) . ? C9 H9 0.9500 . ? C10 C11 1.355(5) . ? C10 H10 0.9500 . ? C11 C12 1.379(5) . ? C12 C13 1.388(5) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.384(4) . ? C14 C15 1.392(4) . ? C15 C16 1.392(4) . ? C15 H15 0.9500 . ? C16 C17 1.386(5) . ? C16 H16 0.9500 . ? C17 C18 1.374(5) . ? C18 C19 1.386(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O20 H20 0.8400 . ? 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 O20 C1 C8 109.2(2) . . ? O20 C1 C2 108.1(2) . . ? C8 C1 C2 112.9(3) . . ? O20 C1 C14 105.7(2) . . ? C8 C1 C14 108.4(2) . . ? C2 C1 C14 112.2(2) . . ? C3 C2 C7 119.4(3) . . ? C3 C2 C1 120.8(3) . . ? C7 C2 C1 119.6(3) . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 Br1 119.5(3) . . ? C4 C5 Br1 119.5(3) . . ? C5 C6 C7 119.1(3) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C2 C7 C6 120.8(3) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C13 118.7(3) . . ? C9 C8 C1 120.0(3) . . ? C13 C8 C1 121.1(3) . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C10 C11 C12 121.8(3) . . ? C10 C11 Br2 119.1(3) . . ? C12 C11 Br2 119.1(3) . . ? C11 C12 C13 119.1(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C8 120.6(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C19 C14 C15 118.7(3) . . ? C19 C14 C1 120.1(3) . . ? C15 C14 C1 121.1(3) . . ? C16 C15 C14 120.8(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C16 120.4(3) . . ? C18 C17 Br3 118.9(3) . . ? C16 C17 Br3 120.7(3) . . ? C17 C18 C19 120.1(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C14 C19 C18 120.7(3) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C1 O20 H20 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 O20 C1 C2 C3 89.9(3) . . . . ? C8 C1 C2 C3 -149.1(3) . . . . ? C14 C1 C2 C3 -26.3(4) . . . . ? O20 C1 C2 C7 -85.0(4) . . . . ? C8 C1 C2 C7 35.9(4) . . . . ? C14 C1 C2 C7 158.8(3) . . . . ? C7 C2 C3 C4 -0.8(5) . . . . ? C1 C2 C3 C4 -175.7(3) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C3 C4 C5 Br1 -177.4(2) . . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? Br1 C5 C6 C7 177.5(2) . . . . ? C3 C2 C7 C6 0.9(5) . . . . ? C1 C2 C7 C6 176.0(3) . . . . ? C5 C6 C7 C2 -0.4(5) . . . . ? O20 C1 C8 C9 -18.8(4) . . . . ? C2 C1 C8 C9 -139.1(3) . . . . ? C14 C1 C8 C9 96.0(3) . . . . ? O20 C1 C8 C13 166.8(3) . . . . ? C2 C1 C8 C13 46.5(4) . . . . ? C14 C1 C8 C13 -78.4(4) . . . . ? C13 C8 C9 C10 0.2(5) . . . . ? C1 C8 C9 C10 -174.3(3) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C9 C10 C11 C12 -1.2(5) . . . . ? C9 C10 C11 Br2 176.9(3) . . . . ? C10 C11 C12 C13 0.3(5) . . . . ? Br2 C11 C12 C13 -177.8(2) . . . . ? C11 C12 C13 C8 0.8(5) . . . . ? C9 C8 C13 C12 -1.1(5) . . . . ? C1 C8 C13 C12 173.4(3) . . . . ? O20 C1 C14 C19 178.4(3) . . . . ? C8 C1 C14 C19 61.4(4) . . . . ? C2 C1 C14 C19 -64.0(4) . . . . ? O20 C1 C14 C15 0.3(4) . . . . ? C8 C1 C14 C15 -116.7(3) . . . . ? C2 C1 C14 C15 117.9(3) . . . . ? C19 C14 C15 C16 -0.9(5) . . . . ? C1 C14 C15 C16 177.3(3) . . . . ? C14 C15 C16 C17 -0.3(5) . . . . ? C15 C16 C17 C18 1.3(5) . . . . ? C15 C16 C17 Br3 -179.5(2) . . . . ? C16 C17 C18 C19 -1.1(5) . . . . ? Br3 C17 C18 C19 179.7(3) . . . . ? C15 C14 C19 C18 1.1(5) . . . . ? C1 C14 C19 C18 -177.1(3) . . . . ? C17 C18 C19 C14 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.450 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.097 #data_mvtri data_2/B _database_code_depnum_ccdc_archive 'CCDC 658147' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 I3 O' _chemical_formula_sum 'C19 H13 I3 O' _chemical_formula_weight 637.99 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' I I -0.4742 1.8119 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.8300(3) _cell_length_b 11.2826(4) _cell_length_c 19.1611(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1908.9(1) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9971 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 4.914 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1565 _exptl_absorpt_correction_T_max 0.4399 _exptl_absorpt_process_details Blessing _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_source 'sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'CCD scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16970 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.85 _reflns_number_total 4532 _reflns_number_gt 4350 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.0 (Bruker, 2006)' _computing_cell_refinement 'APEX2 V2.0 (Bruker, 2006)' _computing_data_reduction 'APEX2 V2.0 (Bruker, 2006)' _computing_structure_solution 'SIR-97 (Altomare, 1997)' _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^)+(0.0399P)^2^+1.8232P] 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 SHELXL _refine_ls_extinction_coef 0.0048(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 4532 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_obs 0.0712 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 -0.26714(3) 0.44372(3) 0.761838(15) 0.03645(10) Uani 1 1 d . . . I2 I 0.74572(4) 0.73157(2) 0.487157(19) 0.04384(10) Uani 1 1 d . . . I3 I 0.74348(3) -0.07902(2) 0.692485(14) 0.03430(9) Uani 1 1 d . . . C1 C 0.2894(4) 0.3071(3) 0.56181(18) 0.0170(7) Uani 1 1 d . . . C2 C 0.1581(4) 0.3396(3) 0.6108(2) 0.0184(7) Uani 1 1 d . . . C3 C 0.1014(4) 0.2573(4) 0.6584(2) 0.0206(8) Uani 1 1 d . . . H3 H 0.1474 0.1814 0.6620 0.025 Uiso 1 1 calc R . . C4 C -0.0231(4) 0.2855(4) 0.7008(2) 0.0253(9) Uani 1 1 d . . . H4 H -0.0608 0.2296 0.7336 0.030 Uiso 1 1 calc R . . C5 C -0.0900(4) 0.3958(4) 0.6944(2) 0.0263(9) Uani 1 1 d . . . C6 C -0.0381(5) 0.4773(4) 0.6466(2) 0.0283(9) Uani 1 1 d . . . H6 H -0.0864 0.5522 0.6424 0.034 Uiso 1 1 calc R . . C7 C 0.0859(4) 0.4495(4) 0.6043(2) 0.0252(8) Uani 1 1 d . . . H7 H 0.1213 0.5054 0.5711 0.030 Uiso 1 1 calc R . . C8 C 0.3897(4) 0.4151(3) 0.54417(19) 0.0173(7) Uani 1 1 d . . . C9 C 0.4408(4) 0.4292(4) 0.4759(2) 0.0210(7) Uani 1 1 d . . . H9 H 0.4070 0.3767 0.4403 0.025 Uiso 1 1 calc R . . C10 C 0.5421(5) 0.5210(4) 0.4597(2) 0.0255(8) Uani 1 1 d . . . H10 H 0.5775 0.5306 0.4132 0.031 Uiso 1 1 calc R . . C11 C 0.5899(4) 0.5970(4) 0.5113(3) 0.0276(9) Uani 1 1 d . . . C12 C 0.5379(5) 0.5855(4) 0.5792(2) 0.0268(8) Uani 1 1 d . . . H12 H 0.5715 0.6385 0.6145 0.032 Uiso 1 1 calc R . . C13 C 0.4364(5) 0.4957(4) 0.5950(2) 0.0237(8) Uani 1 1 d . . . H13 H 0.3980 0.4890 0.6412 0.028 Uiso 1 1 calc R . . C14 C 0.3937(4) 0.2113(3) 0.59332(19) 0.0157(7) Uani 1 1 d . . . C15 C 0.4161(4) 0.1040(3) 0.5602(2) 0.0198(7) Uani 1 1 d . . . H15 H 0.3627 0.0870 0.5183 0.024 Uiso 1 1 calc R . . C16 C 0.5163(4) 0.0198(4) 0.5875(2) 0.0223(8) Uani 1 1 d . . . H16 H 0.5315 -0.0534 0.5641 0.027 Uiso 1 1 calc R . . C17 C 0.5927(4) 0.0437(4) 0.6485(2) 0.0225(8) Uani 1 1 d . . . C18 C 0.5697(5) 0.1505(4) 0.6836(2) 0.0248(8) Uani 1 1 d . . . H18 H 0.6215 0.1666 0.7260 0.030 Uiso 1 1 calc R . . C19 C 0.4701(5) 0.2327(4) 0.6557(2) 0.0235(8) Uani 1 1 d . . . H19 H 0.4536 0.3053 0.6796 0.028 Uiso 1 1 calc R . . O20 O 0.2278(3) 0.2577(2) 0.49910(14) 0.0224(5) Uani 1 1 d . . . H20 H 0.1351 0.2878 0.4897 0.034 Uiso 1 1 d 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 0.02057(13) 0.05067(18) 0.03810(15) -0.02276(12) 0.00665(11) -0.00152(12) I2 0.03569(17) 0.02294(14) 0.0729(2) 0.00112(12) 0.02083(17) -0.00749(14) I3 0.03161(15) 0.03969(16) 0.03160(14) 0.01249(10) 0.00202(12) 0.01560(13) C1 0.0131(16) 0.0198(16) 0.0181(16) -0.0013(13) -0.0004(13) 0.0000(13) C2 0.0132(16) 0.0224(19) 0.0194(17) -0.0024(14) 0.0004(14) -0.0010(13) C3 0.0181(17) 0.0190(19) 0.0246(19) 0.0006(15) 0.0044(15) 0.0020(14) C4 0.0176(17) 0.031(2) 0.028(2) -0.0038(17) 0.0054(15) -0.0062(16) C5 0.0183(17) 0.033(2) 0.027(2) -0.0135(17) 0.0013(16) -0.0002(16) C6 0.0222(19) 0.028(2) 0.034(2) -0.0027(18) 0.0003(18) 0.0095(17) C7 0.0228(18) 0.025(2) 0.028(2) 0.0029(18) 0.0008(15) 0.0048(17) C8 0.0130(14) 0.0175(18) 0.0215(17) 0.0007(14) -0.0007(13) 0.0025(13) C9 0.0215(16) 0.0207(19) 0.0208(17) 0.0012(15) 0.0018(14) 0.0035(15) C10 0.0237(19) 0.025(2) 0.027(2) 0.0070(16) 0.0096(16) 0.0042(16) C11 0.0208(18) 0.0158(19) 0.046(2) 0.0063(17) 0.0062(18) 0.0027(15) C12 0.0282(19) 0.0203(19) 0.032(2) 0.0000(17) 0.0013(17) -0.0030(16) C13 0.0239(19) 0.023(2) 0.024(2) 0.0003(16) 0.0045(16) -0.0028(16) C14 0.0119(15) 0.0189(18) 0.0162(16) 0.0013(13) 0.0034(13) 0.0014(13) C15 0.0183(17) 0.0200(18) 0.0210(17) 0.0006(14) 0.0009(14) -0.0020(14) C16 0.0249(19) 0.0184(19) 0.0235(19) 0.0005(15) 0.0007(16) 0.0017(15) C17 0.0185(16) 0.025(2) 0.0244(18) 0.0071(16) 0.0025(15) 0.0019(15) C18 0.0222(19) 0.032(2) 0.0199(19) 0.0014(16) -0.0036(15) 0.0003(16) C19 0.0239(18) 0.021(2) 0.026(2) -0.0026(16) -0.0053(16) 0.0028(16) O20 0.0170(12) 0.0274(13) 0.0227(11) -0.0021(10) -0.0051(11) -0.0010(11) _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 C5 2.099(4) . ? I2 C11 2.100(4) . ? I3 C17 2.098(4) . ? C1 O20 1.432(4) . ? C1 C2 1.537(5) . ? C1 C14 1.542(5) . ? C1 C8 1.544(5) . ? C2 C3 1.394(5) . ? C2 C7 1.400(6) . ? C3 C4 1.405(5) . ? C3 H3 0.9500 . ? C4 C5 1.383(6) . ? C4 H4 0.9500 . ? C5 C6 1.376(7) . ? C6 C7 1.398(6) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.393(5) . ? C8 C13 1.396(6) . ? C9 C10 1.403(6) . ? C9 H9 0.9500 . ? C10 C11 1.375(7) . ? C10 H10 0.9500 . ? C11 C12 1.387(6) . ? C12 C13 1.386(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.382(5) . ? C14 C19 1.393(5) . ? C15 C16 1.400(5) . ? C15 H15 0.9500 . ? C16 C17 1.375(6) . ? C16 H16 0.9500 . ? C17 C18 1.395(6) . ? C18 C19 1.385(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O20 H20 0.9033 . ? 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 O20 C1 C2 108.6(3) . . ? O20 C1 C14 106.5(3) . . ? C2 C1 C14 112.2(3) . . ? O20 C1 C8 109.9(3) . . ? C2 C1 C8 112.2(3) . . ? C14 C1 C8 107.2(3) . . ? C3 C2 C7 119.0(4) . . ? C3 C2 C1 120.7(3) . . ? C7 C2 C1 120.1(3) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 121.2(4) . . ? C6 C5 I1 119.0(3) . . ? C4 C5 I1 119.7(3) . . ? C5 C6 C7 119.8(4) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C2 120.3(4) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C9 C8 C13 119.1(4) . . ? C9 C8 C1 118.8(3) . . ? C13 C8 C1 122.1(3) . . ? C8 C9 C10 119.9(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 121.0(4) . . ? C10 C11 I2 119.6(3) . . ? C12 C11 I2 119.4(3) . . ? C13 C12 C11 119.2(4) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 121.0(4) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C15 C14 C19 118.5(4) . . ? C15 C14 C1 121.3(3) . . ? C19 C14 C1 120.3(3) . . ? C14 C15 C16 120.8(4) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 119.7(4) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.5(4) . . ? C16 C17 I3 121.6(3) . . ? C18 C17 I3 117.9(3) . . ? C19 C18 C17 119.0(4) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 C14 121.6(4) . . ? C18 C19 H19 119.2 . . ? C14 C19 H19 119.2 . . ? C1 O20 H20 111.4 . . ? 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 O20 C1 C2 C3 89.3(4) . . . . ? C14 C1 C2 C3 -28.1(5) . . . . ? C8 C1 C2 C3 -149.0(3) . . . . ? O20 C1 C2 C7 -85.6(4) . . . . ? C14 C1 C2 C7 157.0(3) . . . . ? C8 C1 C2 C7 36.1(5) . . . . ? C7 C2 C3 C4 -2.1(6) . . . . ? C1 C2 C3 C4 -177.1(4) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C3 C4 C5 C6 0.9(6) . . . . ? C3 C4 C5 I1 -176.1(3) . . . . ? C4 C5 C6 C7 -1.0(7) . . . . ? I1 C5 C6 C7 176.0(3) . . . . ? C5 C6 C7 C2 -0.5(6) . . . . ? C3 C2 C7 C6 2.1(6) . . . . ? C1 C2 C7 C6 177.0(4) . . . . ? O20 C1 C8 C9 -17.7(4) . . . . ? C2 C1 C8 C9 -138.6(3) . . . . ? C14 C1 C8 C9 97.7(4) . . . . ? O20 C1 C8 C13 165.3(3) . . . . ? C2 C1 C8 C13 44.4(5) . . . . ? C14 C1 C8 C13 -79.3(4) . . . . ? C13 C8 C9 C10 2.3(6) . . . . ? C1 C8 C9 C10 -174.8(3) . . . . ? C8 C9 C10 C11 -0.3(6) . . . . ? C9 C10 C11 C12 -0.9(6) . . . . ? C9 C10 C11 I2 178.5(3) . . . . ? C10 C11 C12 C13 0.0(6) . . . . ? I2 C11 C12 C13 -179.3(3) . . . . ? C11 C12 C13 C8 2.0(6) . . . . ? C9 C8 C13 C12 -3.2(6) . . . . ? C1 C8 C13 C12 173.8(4) . . . . ? O20 C1 C14 C15 1.8(4) . . . . ? C2 C1 C14 C15 120.5(4) . . . . ? C8 C1 C14 C15 -115.8(4) . . . . ? O20 C1 C14 C19 -179.5(3) . . . . ? C2 C1 C14 C19 -60.8(4) . . . . ? C8 C1 C14 C19 62.9(4) . . . . ? C19 C14 C15 C16 -1.7(6) . . . . ? C1 C14 C15 C16 177.0(3) . . . . ? C14 C15 C16 C17 0.5(6) . . . . ? C15 C16 C17 C18 0.7(6) . . . . ? C15 C16 C17 I3 179.6(3) . . . . ? C16 C17 C18 C19 -0.8(6) . . . . ? I3 C17 C18 C19 -179.7(3) . . . . ? C17 C18 C19 C14 -0.4(6) . . . . ? C15 C14 C19 C18 1.7(6) . . . . ? C1 C14 C19 C18 -177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.652 _refine_diff_density_min -1.080 _refine_diff_density_rms 0.123 #data_tr143mo data_2C _database_code_depnum_ccdc_archive 'CCDC 658148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 I3 O, C H2 Cl2' _chemical_formula_sum 'C20 H15 Cl2 I3 O' _chemical_formula_weight 722.92 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A bm2' _symmetry_space_group_name_Hall 'A 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, z+1/2' 'x, -y, z+1/2' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x, y+1/2, z+1' 'x, -y+1/2, z+1' _cell_length_a 12.2182(4) _cell_length_b 20.4790(5) _cell_length_c 8.5939(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2150.34(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6423 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.8 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 4.617 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2596 _exptl_absorpt_correction_T_max 0.7692 _exptl_absorpt_process_details Blessing _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_source 'sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'CCD scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9554 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.86 _reflns_number_total 2546 _reflns_number_gt 2462 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.0 (Bruker, 2006)' _computing_cell_refinement 'APEX2 V2.0 (Bruker, 2006)' _computing_data_reduction 'APEX2 V2.0 (Bruker, 2006)' _computing_structure_solution 'SIR-97 (Altomare, 1997)' _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^)+(0.0462P)^2^+7.6243P] 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 0.02(4) _refine_ls_number_reflns 2546 _refine_ls_number_parameters 126 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_obs 0.0751 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 I2 I 0.17893(3) 0.014137(13) 0.39999(5) 0.03665(11) Uani 1 1 d . . . I1 I 0.46537(4) 0.2500 1.45267(6) 0.03611(13) Uani 1 2 d S . . O20 O 0.0128(3) 0.2500 0.9429(6) 0.0236(8) Uani 1 2 d S . . H20 H -0.0085 0.2500 1.0352 0.028 Uiso 1 2 d SR . . C1 C 0.1230(5) 0.2500 0.8859(8) 0.0220(11) Uani 1 2 d S . . C8 C 0.1362(4) 0.18985(19) 0.7812(5) 0.0190(8) Uani 1 1 d . . . C13 C 0.2397(4) 0.1716(2) 0.7266(6) 0.0268(9) Uani 1 1 d . . . H13 H 0.3026 0.1941 0.7631 0.032 Uiso 1 1 calc R . . C12 C 0.2520(4) 0.1212(2) 0.6202(6) 0.0297(10) Uani 1 1 d . . . H12 H 0.3227 0.1094 0.5838 0.036 Uiso 1 1 calc R . . C11 C 0.1597(4) 0.0881(2) 0.5673(5) 0.0240(9) Uani 1 1 d . . . C10 C 0.0576(4) 0.1038(2) 0.6225(6) 0.0263(9) Uani 1 1 d . . . H10 H -0.0049 0.0804 0.5878 0.032 Uiso 1 1 calc R . . C9 C 0.0461(4) 0.15453(19) 0.7303(6) 0.0222(8) Uani 1 1 d . . . H9 H -0.0245 0.1650 0.7693 0.027 Uiso 1 1 calc R . . C2 C 0.2030(5) 0.2500 1.0224(7) 0.0186(11) Uani 1 2 d S . . C3 C 0.2368(4) 0.1914(2) 1.0894(5) 0.0256(9) Uani 1 1 d . . . H3 H 0.2104 0.1512 1.0490 0.031 Uiso 1 1 calc R . . C4 C 0.3096(4) 0.1912(2) 1.2164(6) 0.0280(10) Uani 1 1 d . . . H4 H 0.3331 0.1512 1.2610 0.034 Uiso 1 1 calc R . . C5 C 0.3465(5) 0.2500 1.2752(7) 0.0267(13) Uani 1 2 d S . . C1L C 0.5000 0.0000 0.7668(19) 0.076(3) Uani 1 2 d S . . H1L1 H 0.5641 0.0055 0.7007 0.092 Uiso 1 1 d R . . Cl1 Cl 0.48285(19) 0.07045(10) 0.8815(4) 0.0785(6) 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 I2 0.0500(2) 0.02880(15) 0.03121(16) -0.01087(13) 0.00597(15) -0.00574(12) I1 0.0240(2) 0.0611(3) 0.02326(19) 0.000 -0.00547(18) 0.000 O20 0.0194(19) 0.0334(18) 0.018(2) 0.000 0.0030(19) 0.000 C1 0.020(3) 0.028(2) 0.018(3) 0.000 0.003(2) 0.000 C8 0.0184(19) 0.0214(17) 0.0171(17) 0.0019(15) 0.0000(16) -0.0006(15) C13 0.020(2) 0.030(2) 0.030(2) -0.0078(18) 0.0025(19) -0.0039(17) C12 0.030(2) 0.033(2) 0.026(2) -0.006(2) 0.005(2) -0.0028(19) C11 0.036(3) 0.0172(18) 0.018(2) -0.0032(15) 0.0014(18) -0.0039(16) C10 0.027(2) 0.026(2) 0.027(2) 0.0041(18) -0.0050(18) -0.0047(18) C9 0.0183(19) 0.0225(17) 0.026(2) 0.0032(17) -0.0016(18) 0.0004(15) C2 0.018(3) 0.025(3) 0.013(3) 0.000 0.004(2) 0.000 C3 0.032(2) 0.0243(19) 0.020(2) 0.0003(16) -0.0044(19) -0.0009(17) C4 0.028(2) 0.032(2) 0.024(2) 0.0055(19) -0.0046(18) 0.0021(17) C5 0.020(3) 0.044(4) 0.015(3) 0.000 0.001(2) 0.000 C1L 0.077(8) 0.080(7) 0.072(8) 0.000 0.000 -0.028(7) Cl1 0.0695(12) 0.0684(10) 0.0974(18) 0.0025(11) -0.0158(12) -0.0115(9) _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 I2 C11 2.102(4) . ? I1 C5 2.106(7) . ? O20 C1 1.433(7) . ? C1 C2 1.527(9) . ? C1 C8 1.534(6) . ? C1 C8 1.534(6) 8_554 ? C8 C9 1.388(6) . ? C8 C13 1.399(6) . ? C13 C12 1.386(7) . ? C12 C11 1.392(7) . ? C11 C10 1.373(7) . ? C10 C9 1.398(7) . ? C2 C3 1.393(5) 8_554 ? C2 C3 1.393(5) . ? C3 C4 1.408(7) . ? C4 C5 1.381(6) . ? C5 C4 1.381(6) 8_554 ? C1L Cl1 1.760(9) . ? C1L Cl1 1.760(9) 2_655 ? 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 O20 C1 C2 109.8(5) . . ? O20 C1 C8 107.4(3) . . ? C2 C1 C8 112.6(3) . . ? O20 C1 C8 107.4(3) . 8_554 ? C2 C1 C8 112.6(3) . 8_554 ? C8 C1 C8 106.8(5) . 8_554 ? C9 C8 C13 118.1(4) . . ? C9 C8 C1 121.3(4) . . ? C13 C8 C1 120.5(4) . . ? C12 C13 C8 121.2(4) . . ? C13 C12 C11 119.3(5) . . ? C10 C11 C12 120.6(4) . . ? C10 C11 I2 120.4(3) . . ? C12 C11 I2 119.0(4) . . ? C11 C10 C9 119.6(4) . . ? C8 C9 C10 121.1(4) . . ? C3 C2 C3 118.9(6) 8_554 . ? C3 C2 C1 120.5(3) 8_554 . ? C3 C2 C1 120.5(3) . . ? C2 C3 C4 120.7(4) . . ? C5 C4 C3 119.2(4) . . ? C4 C5 C4 121.3(6) . 8_554 ? C4 C5 I1 119.3(3) . . ? C4 C5 I1 119.3(3) 8_554 . ? Cl1 C1L Cl1 111.9(9) . 2_655 ? 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 O20 C1 C8 C9 13.3(6) . . . . ? C2 C1 C8 C9 134.2(5) . . . . ? C8 C1 C8 C9 -101.7(5) 8_554 . . . ? O20 C1 C8 C13 -170.7(4) . . . . ? C2 C1 C8 C13 -49.7(6) . . . . ? C8 C1 C8 C13 74.3(6) 8_554 . . . ? C9 C8 C13 C12 2.4(7) . . . . ? C1 C8 C13 C12 -173.8(5) . . . . ? C8 C13 C12 C11 -0.3(8) . . . . ? C13 C12 C11 C10 -1.7(7) . . . . ? C13 C12 C11 I2 177.8(4) . . . . ? C12 C11 C10 C9 1.5(7) . . . . ? I2 C11 C10 C9 -178.1(3) . . . . ? C13 C8 C9 C10 -2.6(6) . . . . ? C1 C8 C9 C10 173.5(4) . . . . ? C11 C10 C9 C8 0.7(7) . . . . ? O20 C1 C2 C3 -87.6(5) . . . 8_554 ? C8 C1 C2 C3 152.8(5) . . . 8_554 ? C8 C1 C2 C3 32.0(7) 8_554 . . 8_554 ? O20 C1 C2 C3 87.6(5) . . . . ? C8 C1 C2 C3 -32.0(7) . . . . ? C8 C1 C2 C3 -152.8(5) 8_554 . . . ? C3 C2 C3 C4 -4.1(9) 8_554 . . . ? C1 C2 C3 C4 -179.4(5) . . . . ? C2 C3 C4 C5 0.7(8) . . . . ? C3 C4 C5 C4 2.9(10) . . . 8_554 ? C3 C4 C5 I1 -175.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.920 _refine_diff_density_min -1.217 _refine_diff_density_rms 0.134 #data_mvtr34 data_2D _database_code_depnum_ccdc_archive 'CCDC 658149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 I3 O, 0.5(C6 H6)' _chemical_formula_sum 'C22 H16 I3 O' _chemical_formula_weight 677.05 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4517(2) _cell_length_b 12.7694(3) _cell_length_c 13.9219(3) _cell_angle_alpha 105.7630(10) _cell_angle_beta 100.9760(10) _cell_angle_gamma 96.7710(10) _cell_volume 1066.01(5) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 7405 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630 _exptl_absorpt_coefficient_mu 4.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2925 _exptl_absorpt_correction_T_max 0.5213 _exptl_absorpt_process_details Blessing _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed Tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_method 'CCD scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13295 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5101 _reflns_number_gt 4399 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 V2.0 (Bruker, 2006)' _computing_cell_refinement 'APEX2 V2.0 (Bruker, 2006)' _computing_data_reduction 'APEX2 V2.0 (Bruker, 2006)' _computing_structure_solution 'SIR-97 (Altomare, 1997)' _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^)+(0.0360P)^2^+1.1365P] 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 5101 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_obs 0.0691 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.92643(4) 0.416515(19) 0.154215(17) 0.03649(7) Uani 1 1 d . . . I2 I 0.43763(5) -0.40751(2) 0.14591(2) 0.04635(8) Uani 1 1 d . . . I3 I -0.07650(5) 0.21543(2) 0.626551(16) 0.04422(8) Uani 1 1 d . . . C1 C 0.1628(5) 0.0666(3) 0.1871(2) 0.0228(6) Uani 1 1 d . . . O20 O -0.0278(4) 0.05533(19) 0.10793(15) 0.0287(5) Uani 1 1 d . . . H20 H -0.0230 0.1302 0.1102 0.043 Uiso 1 1 d R . . C2 C 0.3376(5) 0.1545(3) 0.1789(2) 0.0236(6) Uani 1 1 d . . . C3 C 0.4102(5) 0.2570(3) 0.2531(2) 0.0296(7) Uani 1 1 d . . . H3 H 0.3494 0.2745 0.3113 0.036 Uiso 1 1 calc R . . C4 C 0.5699(6) 0.3341(3) 0.2438(2) 0.0317(7) Uani 1 1 d . . . H4 H 0.6181 0.4036 0.2952 0.038 Uiso 1 1 calc R . . C5 C 0.6584(5) 0.3089(3) 0.1590(2) 0.0282(6) Uani 1 1 d . . . C6 C 0.5820(5) 0.2091(3) 0.0813(2) 0.0285(7) Uani 1 1 d . . . H6 H 0.6388 0.1931 0.0218 0.034 Uiso 1 1 calc R . . C7 C 0.4216(5) 0.1333(3) 0.0918(2) 0.0262(6) Uani 1 1 d . . . H7 H 0.3680 0.0654 0.0386 0.031 Uiso 1 1 calc R . . C8 C 0.2287(5) -0.0469(2) 0.1707(2) 0.0226(6) Uani 1 1 d . . . C13 C 0.4424(5) -0.0566(3) 0.2036(2) 0.0263(6) Uani 1 1 d . . . H13 H 0.5500 0.0082 0.2305 0.032 Uiso 1 1 calc R . . C12 C 0.5002(5) -0.1590(3) 0.1976(2) 0.0288(6) Uani 1 1 d . . . H12 H 0.6457 -0.1644 0.2207 0.035 Uiso 1 1 calc R . . C11 C 0.3427(5) -0.2537(3) 0.1574(2) 0.0281(6) Uani 1 1 d . . . C10 C 0.1309(5) -0.2468(3) 0.1233(2) 0.0284(6) Uani 1 1 d . . . H10 H 0.0246 -0.3120 0.0953 0.034 Uiso 1 1 calc R . . C9 C 0.0740(5) -0.1432(3) 0.1303(2) 0.0256(6) Uani 1 1 d . . . H9 H -0.0719 -0.1383 0.1072 0.031 Uiso 1 1 calc R . . C14 C 0.1027(5) 0.1010(2) 0.2921(2) 0.0233(6) Uani 1 1 d . . . C19 C 0.2315(6) 0.0867(3) 0.3786(2) 0.0366(8) Uani 1 1 d . . . H19 H 0.3554 0.0544 0.3724 0.044 Uiso 1 1 calc R . . C18 C 0.1805(6) 0.1194(3) 0.4742(2) 0.0376(8) Uani 1 1 d . . . H18 H 0.2684 0.1086 0.5325 0.045 Uiso 1 1 calc R . . C17 C 0.0019(5) 0.1673(3) 0.4834(2) 0.0280(6) Uani 1 1 d . . . C16 C -0.1255(5) 0.1849(3) 0.3988(2) 0.0301(7) Uani 1 1 d . . . H16 H -0.2468 0.2194 0.4055 0.036 Uiso 1 1 calc R . . C15 C -0.0725(5) 0.1512(3) 0.3038(2) 0.0249(6) Uani 1 1 d . . . H15 H -0.1591 0.1632 0.2459 0.030 Uiso 1 1 calc R . . C1L C 0.3013(9) 0.4442(4) 0.4921(4) 0.0651(14) Uani 1 1 d . . . H1L H 0.1626 0.4050 0.4864 0.078 Uiso 1 1 calc R . . C2L C 0.3227(9) 0.5276(4) 0.4489(4) 0.0683(15) Uani 1 1 d . . . H2L H 0.1994 0.5472 0.4135 0.082 Uiso 1 1 calc R . . C3L C 0.5231(11) 0.5828(4) 0.4570(3) 0.0682(16) Uani 1 1 d . . . H3L H 0.5390 0.6407 0.4267 0.082 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 0.03789(14) 0.03170(12) 0.03739(12) 0.00973(9) 0.00675(9) 0.00150(9) I2 0.05805(17) 0.03216(13) 0.05373(15) 0.01583(11) 0.01399(12) 0.01856(11) I3 0.06222(18) 0.05378(16) 0.02393(11) 0.01249(10) 0.01985(10) 0.02068(13) C1 0.0227(14) 0.0290(15) 0.0154(11) 0.0055(10) 0.0013(10) 0.0075(12) O20 0.0279(12) 0.0341(12) 0.0207(9) 0.0051(8) -0.0010(8) 0.0107(9) C2 0.0255(15) 0.0272(15) 0.0194(12) 0.0091(11) 0.0030(11) 0.0084(12) C3 0.0331(17) 0.0308(16) 0.0234(14) 0.0028(12) 0.0087(12) 0.0089(13) C4 0.0374(18) 0.0263(16) 0.0276(15) 0.0015(12) 0.0070(13) 0.0086(14) C5 0.0295(16) 0.0273(15) 0.0285(14) 0.0113(12) 0.0036(12) 0.0058(13) C6 0.0359(18) 0.0312(16) 0.0182(12) 0.0067(12) 0.0053(12) 0.0081(13) C7 0.0288(16) 0.0291(15) 0.0183(12) 0.0036(11) 0.0037(11) 0.0064(12) C8 0.0261(15) 0.0265(14) 0.0160(11) 0.0064(10) 0.0058(10) 0.0064(12) C13 0.0230(15) 0.0305(16) 0.0232(13) 0.0058(12) 0.0040(11) 0.0044(12) C12 0.0264(16) 0.0358(17) 0.0262(14) 0.0108(13) 0.0062(12) 0.0098(13) C11 0.0392(18) 0.0275(15) 0.0245(13) 0.0108(12) 0.0155(12) 0.0132(13) C10 0.0332(17) 0.0274(15) 0.0246(14) 0.0076(12) 0.0099(12) 0.0007(13) C9 0.0228(15) 0.0321(16) 0.0222(13) 0.0071(11) 0.0074(11) 0.0055(12) C14 0.0255(15) 0.0259(14) 0.0180(12) 0.0056(11) 0.0039(11) 0.0074(12) C19 0.0399(19) 0.050(2) 0.0231(14) 0.0091(14) 0.0076(13) 0.0264(17) C18 0.051(2) 0.047(2) 0.0206(14) 0.0135(14) 0.0059(13) 0.0251(17) C17 0.0378(18) 0.0283(15) 0.0193(13) 0.0077(11) 0.0096(12) 0.0057(13) C16 0.0263(16) 0.0382(18) 0.0256(14) 0.0064(13) 0.0079(12) 0.0101(14) C15 0.0224(15) 0.0323(16) 0.0192(12) 0.0078(11) 0.0017(10) 0.0071(12) C1L 0.070(3) 0.040(2) 0.068(3) -0.010(2) 0.021(3) -0.003(2) C2L 0.080(4) 0.053(3) 0.048(2) -0.007(2) -0.013(2) 0.021(3) C3L 0.122(5) 0.039(2) 0.043(2) 0.0112(19) 0.021(3) 0.015(3) _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 C5 2.101(3) . ? I2 C11 2.100(3) . ? I3 C17 2.096(3) . ? C1 O20 1.450(3) . ? C1 C8 1.528(4) . ? C1 C2 1.538(4) . ? C1 C14 1.546(4) . ? C2 C3 1.391(4) . ? C2 C7 1.393(4) . ? C3 C4 1.389(5) . ? C4 C5 1.383(4) . ? C5 C6 1.392(4) . ? C6 C7 1.390(5) . ? C8 C9 1.396(4) . ? C8 C13 1.399(4) . ? C13 C12 1.388(5) . ? C12 C11 1.390(5) . ? C11 C10 1.380(5) . ? C10 C9 1.397(5) . ? C14 C15 1.378(4) . ? C14 C19 1.395(4) . ? C19 C18 1.397(4) . ? C18 C17 1.378(5) . ? C17 C16 1.391(4) . ? C16 C15 1.396(4) . ? C1L C3L 1.350(8) 2_666 ? C1L C2L 1.365(8) . ? C2L C3L 1.366(8) . ? C3L C1L 1.350(8) 2_666 ? 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 O20 C1 C8 107.7(2) . . ? O20 C1 C2 108.3(2) . . ? C8 C1 C2 112.6(2) . . ? O20 C1 C14 108.0(2) . . ? C8 C1 C14 108.7(2) . . ? C2 C1 C14 111.5(2) . . ? C3 C2 C7 118.1(3) . . ? C3 C2 C1 122.7(3) . . ? C7 C2 C1 119.1(3) . . ? C4 C3 C2 121.2(3) . . ? C5 C4 C3 119.6(3) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 I1 119.4(2) . . ? C6 C5 I1 119.9(2) . . ? C7 C6 C5 119.1(3) . . ? C6 C7 C2 121.4(3) . . ? C9 C8 C13 118.3(3) . . ? C9 C8 C1 120.5(3) . . ? C13 C8 C1 120.9(3) . . ? C12 C13 C8 121.2(3) . . ? C13 C12 C11 119.3(3) . . ? C10 C11 C12 120.8(3) . . ? C10 C11 I2 121.0(2) . . ? C12 C11 I2 118.2(2) . . ? C11 C10 C9 119.5(3) . . ? C8 C9 C10 120.9(3) . . ? C15 C14 C19 118.4(3) . . ? C15 C14 C1 121.0(2) . . ? C19 C14 C1 120.5(3) . . ? C14 C19 C18 120.9(3) . . ? C17 C18 C19 119.5(3) . . ? C18 C17 C16 120.5(3) . . ? C18 C17 I3 119.7(2) . . ? C16 C17 I3 119.8(2) . . ? C17 C16 C15 119.0(3) . . ? C14 C15 C16 121.5(3) . . ? C3L C1L C2L 120.1(5) 2_666 . ? C1L C2L C3L 119.4(5) . . ? C1L C3L C2L 120.5(5) 2_666 . ? 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 O20 C1 C2 C3 111.5(3) . . . . ? C8 C1 C2 C3 -129.6(3) . . . . ? C14 C1 C2 C3 -7.1(4) . . . . ? O20 C1 C2 C7 -65.8(3) . . . . ? C8 C1 C2 C7 53.1(3) . . . . ? C14 C1 C2 C7 175.5(3) . . . . ? C7 C2 C3 C4 -3.3(5) . . . . ? C1 C2 C3 C4 179.4(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C3 C4 C5 C6 2.8(5) . . . . ? C3 C4 C5 I1 -172.1(2) . . . . ? C4 C5 C6 C7 -2.5(5) . . . . ? I1 C5 C6 C7 172.3(2) . . . . ? C5 C6 C7 C2 -0.7(5) . . . . ? C3 C2 C7 C6 3.6(5) . . . . ? C1 C2 C7 C6 -179.0(3) . . . . ? O20 C1 C8 C9 -32.0(3) . . . . ? C2 C1 C8 C9 -151.2(3) . . . . ? C14 C1 C8 C9 84.7(3) . . . . ? O20 C1 C8 C13 153.4(3) . . . . ? C2 C1 C8 C13 34.2(3) . . . . ? C14 C1 C8 C13 -89.9(3) . . . . ? C9 C8 C13 C12 -0.8(4) . . . . ? C1 C8 C13 C12 173.9(3) . . . . ? C8 C13 C12 C11 0.5(4) . . . . ? C13 C12 C11 C10 0.2(4) . . . . ? C13 C12 C11 I2 178.4(2) . . . . ? C12 C11 C10 C9 -0.6(4) . . . . ? I2 C11 C10 C9 -178.7(2) . . . . ? C13 C8 C9 C10 0.3(4) . . . . ? C1 C8 C9 C10 -174.4(2) . . . . ? C11 C10 C9 C8 0.4(4) . . . . ? O20 C1 C14 C15 -22.2(4) . . . . ? C8 C1 C14 C15 -138.7(3) . . . . ? C2 C1 C14 C15 96.7(3) . . . . ? O20 C1 C14 C19 161.1(3) . . . . ? C8 C1 C14 C19 44.6(4) . . . . ? C2 C1 C14 C19 -80.1(4) . . . . ? C15 C14 C19 C18 2.0(5) . . . . ? C1 C14 C19 C18 178.9(3) . . . . ? C14 C19 C18 C17 -0.7(6) . . . . ? C19 C18 C17 C16 -1.0(6) . . . . ? C19 C18 C17 I3 179.6(3) . . . . ? C18 C17 C16 C15 1.3(5) . . . . ? I3 C17 C16 C15 -179.3(2) . . . . ? C19 C14 C15 C16 -1.7(5) . . . . ? C1 C14 C15 C16 -178.5(3) . . . . ? C17 C16 C15 C14 0.0(5) . . . . ? C3L C1L C2L C3L 0.4(8) 2_666 . . . ? C1L C2L C3L C1L -0.5(8) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.883 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.138