# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chris Pigge' _publ_contact_author_email CHRIS-PIGGE@UIOWA.EDU _publ_section_title ; Hexagonal crystalline inclusion complexes of 4-iodophenoxy trimesoate ; loop_ _publ_author_name 'Chris Pigge' 'Pradeep P. Kapadia' 'Nigam P Rath' 'Dale C. Swenson' 'Venu R Vangala' # Attachment '4-IodoTMA-pyridine_complex.cif' # Supplementary Material (ESI) for Chemical Communications data_kap71 _database_code_depnum_ccdc_archive 'CCDC 688114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester pyridine solvate ; _chemical_name_common ;Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester pyridine solvate ; _chemical_melting_point ? _chemical_formula_moiety '(C27 H15 O6 I3), 3(C5 H5 N1)' _chemical_formula_sum 'C42 H30 I3 N3 O6' _chemical_formula_weight 1053.39 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M P63/m _symmetry_space_group_name_Hall '-P 6c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 16.5590(18) _cell_length_b 16.5590(18) _cell_length_c 8.4752(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2012.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 8342 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 2.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5555 _exptl_absorpt_correction_T_max 0.6740 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29038 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0142 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1640 _reflns_number_gt 1367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' _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. Several low angle reflections were omitted due to beam-stop shadowing effects. The structure contains channels lined with disordered pyridine solvent molecules. The disordered solvent was modeled with rigid groups (C-C(N) = 1.39A, C-C(N)-C(N) = 120, C-H = 0.95A) of partial occuancy (0.35 and 0.15), each having a group isotropic dispacement parameter. The positions of N atoms was arbitrarily assigned. ; _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^)+(0.0774P)^2^+3.1161P] 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 1640 _refine_ls_number_parameters 83 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.49862(3) 1.32244(3) 0.2500 0.0677(2) Uani 1 2 d S . . C1 C 0.4503(4) 1.1785(3) 0.2500 0.0430(12) Uani 1 2 d S . . C2 C 0.4364(3) 1.1327(3) 0.3914(6) 0.0594(11) Uani 1 1 d . . . H2 H 0.4463 1.1650 0.4885 0.071 Uiso 1 1 calc R . . C3 C 0.4077(4) 1.0385(3) 0.3893(6) 0.0596(11) Uani 1 1 d . . . H3 H 0.3987 1.0056 0.4856 0.072 Uiso 1 1 calc R . . C4 C 0.3925(4) 0.9934(3) 0.2500 0.0440(12) Uani 1 2 d S . . O2 O 0.5028(2) 0.9186(2) 0.2500 0.0474(9) Uani 1 2 d S . . O1 O 0.3573(3) 0.8963(3) 0.2500 0.0515(10) Uani 1 2 d S . . C5 C 0.4201(3) 0.8670(3) 0.2500 0.0376(10) Uani 1 2 d S . . C6 C 0.3736(3) 0.7633(3) 0.2500 0.0349(10) Uani 1 2 d S . . C7 C 0.4304(3) 0.7231(3) 0.2500 0.0361(10) Uani 1 2 d S . . H7 H 0.4964 0.7615 0.2500 0.043 Uiso 1 2 calc SR . . C11 C 0.1659(12) 1.2867(10) 1.2179(19) 0.124(8) Uiso 0.35 1 d PG A -1 H11 H 0.1702 1.3245 1.1303 0.149 Uiso 0.35 1 calc PR A -1 C12 C 0.2331(9) 1.2610(10) 1.240(2) 0.124 Uiso 0.35 1 d PG A -1 H12 H 0.2834 1.2811 1.1679 0.149 Uiso 0.35 1 calc PR A -1 N13 N 0.2268(9) 1.2057(11) 1.368(2) 0.124 Uiso 0.35 1 d PGD A -1 C14 C 0.1532(11) 1.1762(10) 1.4742(17) 0.124 Uiso 0.35 1 d PG A -1 H14 H 0.1489 1.1384 1.5618 0.149 Uiso 0.35 1 calc PR A -1 C15 C 0.0860(10) 1.2019(11) 1.452(2) 0.124 Uiso 0.35 1 d PG A -1 H15 H 0.0357 1.1818 1.5242 0.149 Uiso 0.35 1 calc PR A -1 C16 C 0.0923(11) 1.2572(12) 1.324(2) 0.124 Uiso 0.35 1 d PG A -1 H16 H 0.0464 1.2748 1.3084 0.149 Uiso 0.35 1 calc PR A -1 C31 C 0.126(2) 1.252(2) 1.358(4) 0.117(17) Uiso 0.15 1 d PG B -3 H31 H 0.1215 1.2976 1.4214 0.140 Uiso 0.15 1 calc PR B -3 C32 C 0.0467(17) 1.184(3) 1.282(5) 0.117 Uiso 0.15 1 d PG B -3 H32 H -0.0112 1.1819 1.2931 0.140 Uiso 0.15 1 calc PR B -3 C33 C 0.0526(14) 1.117(2) 1.190(4) 0.117 Uiso 0.15 1 d PG B -3 H33 H -0.0013 1.0703 1.1378 0.140 Uiso 0.15 1 calc PR B -3 C34 C 0.1373(18) 1.120(2) 1.174(5) 0.117 Uiso 0.15 1 d PG B -3 H34 H 0.1413 1.0744 1.1109 0.140 Uiso 0.15 1 calc PR B -3 N35 N 0.2162(12) 1.188(2) 1.250(5) 0.117 Uiso 0.30 2 d SPGD B -3 C36 C 0.2103(19) 1.2548(19) 1.342(5) 0.117 Uiso 0.15 1 d PG B -3 H36 H 0.2642 1.3018 1.3944 0.140 Uiso 0.15 1 calc PR B -3 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 0.0743(4) 0.0307(2) 0.0930(4) 0.000 0.000 0.0225(2) C1 0.034(2) 0.028(2) 0.065(3) 0.000 0.000 0.0147(19) C2 0.076(3) 0.038(2) 0.060(3) -0.0083(18) -0.012(2) 0.026(2) C3 0.077(3) 0.040(2) 0.059(3) 0.0024(18) -0.012(2) 0.027(2) C4 0.036(2) 0.030(2) 0.066(4) 0.000 0.000 0.016(2) O2 0.0312(17) 0.0321(17) 0.074(3) 0.000 0.000 0.0120(14) O1 0.0359(18) 0.0297(17) 0.090(3) 0.000 0.000 0.0173(15) C5 0.036(2) 0.033(2) 0.044(3) 0.000 0.000 0.018(2) C6 0.032(2) 0.033(2) 0.040(3) 0.000 0.000 0.0165(19) C7 0.033(2) 0.035(2) 0.042(3) 0.000 0.000 0.0181(19) _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 C1 2.102(5) . ? C1 C2 1.375(5) . ? C1 C2 1.375(5) 10_556 ? C2 C3 1.385(6) . ? C2 H2 0.9500 . ? C3 C4 1.352(5) . ? C3 H3 0.9500 . ? C4 C3 1.352(5) 10_556 ? C4 O1 1.410(6) . ? O2 C5 1.198(6) . ? O1 C5 1.350(6) . ? C5 C6 1.489(7) . ? C6 C7 1.394(7) 2_665 ? C6 C7 1.397(7) . ? C7 C6 1.394(7) 3_565 ? C7 H7 0.9500 . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C11 H11 0.9500 . ? C12 N13 1.3900 . ? C12 H12 0.9500 . ? N13 C14 1.3900 . ? C14 C15 1.3900 . ? C14 H14 0.9500 . ? C15 C16 1.3900 . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C31 C32 1.3900 . ? C31 C36 1.3900 . ? C31 H31 0.9500 . ? C32 C33 1.3900 . ? C32 H32 0.9500 . ? C33 C34 1.3900 . ? C33 H33 0.9500 . ? C34 N35 1.3900 . ? C34 H34 0.9500 . ? N35 C36 1.3900 . ? C36 H36 0.9500 . ? 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 C2 C1 C2 121.3(5) . 10_556 ? C2 C1 I1 119.3(2) . . ? C2 C1 I1 119.3(2) 10_556 . ? C1 C2 C3 118.6(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C3 121.8(5) 10_556 . ? C3 C4 O1 119.1(3) 10_556 . ? C3 C4 O1 119.1(3) . . ? C5 O1 C4 117.1(4) . . ? O2 C5 O1 123.7(4) . . ? O2 C5 C6 124.8(5) . . ? O1 C5 C6 111.6(4) . . ? C7 C6 C7 120.5(5) 2_665 . ? C7 C6 C5 121.8(4) 2_665 . ? C7 C6 C5 117.8(4) . . ? C6 C7 C6 119.5(5) 3_565 . ? C6 C7 H7 120.2 3_565 . ? C6 C7 H7 120.2 . . ? C12 C11 C16 120.0 . . ? C12 C11 H11 120.0 . . ? C16 C11 H11 120.0 . . ? N13 C12 C11 120.0 . . ? N13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 N13 C14 120.0 . . ? N13 C14 C15 120.0 . . ? N13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.0 . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C32 C31 C36 120.0 . . ? C32 C31 H31 120.0 . . ? C36 C31 H31 120.0 . . ? C31 C32 C33 120.0 . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C34 C33 C32 120.0 . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? N35 C34 C33 120.0 . . ? N35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C36 N35 C34 120.0 . . ? N35 C36 C31 120.0 . . ? N35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? 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 C2 C1 C2 C3 -0.1(9) 10_556 . . . ? I1 C1 C2 C3 -177.7(4) . . . . ? C1 C2 C3 C4 -1.1(8) . . . . ? C2 C3 C4 C3 2.3(10) . . . 10_556 ? C2 C3 C4 O1 -175.7(4) . . . . ? C3 C4 O1 C5 91.0(5) 10_556 . . . ? C3 C4 O1 C5 -91.0(5) . . . . ? C4 O1 C5 O2 0.0 . . . . ? C4 O1 C5 C6 180.0 . . . . ? O2 C5 C6 C7 180.0 . . . 2_665 ? O1 C5 C6 C7 0.0 . . . 2_665 ? O2 C5 C6 C7 0.0 . . . . ? O1 C5 C6 C7 180.0 . . . . ? C7 C6 C7 C6 0.0 2_665 . . 3_565 ? C5 C6 C7 C6 180.0 . . . 3_565 ? C16 C11 C12 N13 0.0 . . . . ? C11 C12 N13 C14 0.0 . . . . ? C12 N13 C14 C15 0.0 . . . . ? N13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C11 0.0 . . . . ? C12 C11 C16 C15 0.0 . . . . ? C36 C31 C32 C33 0.0 . . . . ? C31 C32 C33 C34 0.0 . . . . ? C32 C33 C34 N35 0.0 . . . . ? C33 C34 N35 C36 0.0 . . . . ? C34 N35 C36 C31 0.0 . . . . ? C32 C31 C36 N35 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.736 _refine_diff_density_min -0.971 _refine_diff_density_rms 0.109 # Attachment '4-IodoTMA-benzene_complex.cif' # Supplementary Material (ESI) for Chemical Communications data_fcp722q _database_code_depnum_ccdc_archive 'CCDC 688115' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester benzene solvate ; _chemical_name_common ;Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester benzene solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H15 O6 I3, 1.5(C6 H6)' _chemical_formula_sum 'C36 H24 I3 O6' _chemical_formula_weight 933.25 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 Hexagonal _symmetry_space_group_name_H-M 'P 63/m' _symmetry_space_group_name_Hall '-P 6c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 16.5473(17) _cell_length_b 16.5473(17) _cell_length_c 8.4380(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2000.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9440 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.9 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 894 _exptl_absorpt_coefficient_mu 2.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5554 _exptl_absorpt_correction_T_max 0.7632 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53859 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.87 _reflns_number_total 1700 _reflns_number_gt 1442 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997 - 2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 2001)' _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. Several low angle reflections were omitted due to beam-stop shadowing effects. Benzene molecules (solvent) were included with partial occupancy and modelled with an idealized rigid group. All molecules with partial occupancy were modelled with group isotropic displacement parameters. ; _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^)+(0.0564P)^2^+2.0910P] 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 1700 _refine_ls_number_parameters 81 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.005 _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 -0.32257(2) 0.50405(3) 0.7500 0.0746(2) Uani 1 2 d S . . O2 O 0.0811(2) 0.4979(2) 0.7500 0.0510(7) Uani 1 2 d S . . O1 O 0.10449(19) 0.6444(2) 0.7500 0.0533(8) Uani 1 2 d S . . C6 C 0.2368(3) 0.6271(3) 0.7500 0.0380(8) Uani 1 2 d S . . C5 C 0.1330(3) 0.5810(3) 0.7500 0.0413(8) Uani 1 2 d S . . C7 C 0.2933(3) 0.7235(3) 0.7500 0.0401(8) Uani 1 2 d S . . H7 H 0.2661 0.7623 0.7500 0.048 Uiso 1 2 calc SR . . C4 C 0.0071(3) 0.6097(3) 0.7500 0.0487(10) Uani 1 2 d S . . C1 C -0.1789(3) 0.5517(3) 0.7500 0.0470(9) Uani 1 2 d S . . C3 C -0.0378(2) 0.5945(3) 0.6090(5) 0.0658(10) Uani 1 1 d . . . H3 H -0.0051 0.6038 0.5121 0.079 Uiso 1 1 calc R . . C2 C -0.1329(2) 0.5650(3) 0.6092(5) 0.0671(10) Uani 1 1 d . . . H2 H -0.1656 0.5543 0.5119 0.081 Uiso 1 1 calc R . . C51 C -0.040(4) 0.132(5) 0.706(11) 0.17(4) Uiso 0.08 1 d PG A -1 H51 H -0.0992 0.0837 0.6719 0.207 Uiso 0.08 1 calc PR A -1 C52 C 0.027(6) 0.188(8) 0.596(10) 0.172 Uiso 0.08 1 d PG A -1 H52 H 0.0139 0.1774 0.4856 0.207 Uiso 0.08 1 calc PR A -1 C53 C 0.114(5) 0.259(6) 0.646(11) 0.172 Uiso 0.08 1 d PG A -1 H53 H 0.1596 0.2972 0.5704 0.207 Uiso 0.08 1 calc PR A -1 C54 C 0.133(4) 0.275(5) 0.807(12) 0.172 Uiso 0.08 1 d PG A -1 H54 H 0.1923 0.3231 0.8415 0.207 Uiso 0.08 1 calc PR A -1 C55 C 0.066(6) 0.219(8) 0.918(10) 0.172 Uiso 0.08 1 d PG A -1 H55 H 0.0793 0.2293 1.0277 0.207 Uiso 0.08 1 calc PR A -1 C56 C -0.021(5) 0.148(6) 0.867(10) 0.172 Uiso 0.08 1 d PG A -1 H56 H -0.0665 0.1096 0.9430 0.207 Uiso 0.08 1 calc PR A -1 C61 C 0.239(3) 0.114(3) 0.225(6) 0.19(2) Uiso 0.17 1 d PG B -2 H61 H 0.2641 0.0859 0.2932 0.231 Uiso 0.17 1 calc PR B -2 C62 C 0.228(3) 0.186(3) 0.280(5) 0.192 Uiso 0.17 1 d PG B -2 H62 H 0.2446 0.2084 0.3852 0.231 Uiso 0.17 1 calc PR B -2 C63 C 0.191(3) 0.227(3) 0.180(6) 0.192 Uiso 0.17 1 d PG B -2 H63 H 0.1832 0.2769 0.2171 0.231 Uiso 0.17 1 calc PR B -2 C64 C 0.166(3) 0.195(3) 0.025(6) 0.192 Uiso 0.17 1 d PG B -2 H64 H 0.1414 0.2228 -0.0429 0.231 Uiso 0.17 1 calc PR B -2 C65 C 0.178(3) 0.122(3) -0.029(5) 0.192 Uiso 0.17 1 d PG B -2 H65 H 0.1609 0.1002 -0.1349 0.231 Uiso 0.17 1 calc PR B -2 C66 C 0.214(3) 0.082(3) 0.070(7) 0.192 Uiso 0.17 1 d PG B -2 H66 H 0.2223 0.0318 0.0332 0.231 Uiso 0.17 1 calc PR B -2 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 0.03466(19) 0.0904(3) 0.0940(3) 0.000 0.000 0.02776(17) O2 0.0378(14) 0.0372(14) 0.075(2) 0.000 0.000 0.0161(12) O1 0.0295(13) 0.0395(14) 0.090(2) 0.000 0.000 0.0163(11) C6 0.0345(18) 0.0372(18) 0.042(2) 0.000 0.000 0.0179(15) C5 0.0359(18) 0.041(2) 0.047(2) 0.000 0.000 0.0195(16) C7 0.0374(18) 0.0374(18) 0.049(2) 0.000 0.000 0.0214(16) C4 0.0317(18) 0.042(2) 0.072(3) 0.000 0.000 0.0185(16) C1 0.0307(17) 0.044(2) 0.065(3) 0.000 0.000 0.0178(16) C3 0.0422(16) 0.088(3) 0.063(2) -0.0155(19) 0.0023(15) 0.0298(17) C2 0.0424(16) 0.092(3) 0.061(2) -0.0160(19) -0.0093(15) 0.0293(17) _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 C1 2.097(4) . ? O2 C5 1.202(5) . ? O1 C5 1.349(5) . ? O1 C4 1.414(5) . ? C6 C7 1.388(5) . ? C6 C7 1.399(5) 2_665 ? C6 C5 1.489(5) . ? C7 C6 1.399(5) 3_565 ? C7 H7 0.9500 . ? C4 C3 1.358(4) 10_557 ? C4 C3 1.358(4) . ? C1 C2 1.368(4) 10_557 ? C1 C2 1.368(4) . ? C3 C2 1.396(4) . ? C3 H3 0.9500 . ? C2 H2 0.9500 . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C51 H51 0.9500 . ? C52 C53 1.3900 . ? C52 H52 0.9500 . ? C53 C54 1.3900 . ? C53 H53 0.9500 . ? C54 C55 1.3900 . ? C54 H54 0.9500 . ? C55 C56 1.3900 . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C61 C62 1.3900 . ? C61 C66 1.3900 . ? C61 H61 0.9500 . ? C62 C63 1.3900 . ? C62 H62 0.9500 . ? C63 C64 1.3900 . ? C63 H63 0.9500 . ? C64 C65 1.3900 . ? C64 H64 0.9500 . ? C65 C66 1.3900 . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? 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 C5 O1 C4 117.1(3) . . ? C7 C6 C7 120.3(4) . 2_665 ? C7 C6 C5 122.1(3) . . ? C7 C6 C5 117.7(3) 2_665 . ? O2 C5 O1 124.1(4) . . ? O2 C5 C6 124.6(4) . . ? O1 C5 C6 111.3(3) . . ? C6 C7 C6 119.7(4) . 3_565 ? C6 C7 H7 120.1 . . ? C6 C7 H7 120.1 3_565 . ? C3 C4 C3 122.4(4) 10_557 . ? C3 C4 O1 118.8(2) 10_557 . ? C3 C4 O1 118.8(2) . . ? C2 C1 C2 120.5(4) 10_557 . ? C2 C1 I1 119.7(2) 10_557 . ? C2 C1 I1 119.7(2) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C1 C2 C3 119.8(3) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C52 C51 C56 120.0 . . ? C52 C51 H51 120.0 . . ? C56 C51 H51 120.0 . . ? C51 C52 C53 120.0 . . ? C51 C52 H52 120.0 . . ? C53 C52 H52 120.0 . . ? C52 C53 C54 120.0 . . ? C52 C53 H53 120.0 . . ? C54 C53 H53 120.0 . . ? C55 C54 C53 120.0 . . ? C55 C54 H54 120.0 . . ? C53 C54 H54 120.0 . . ? C54 C55 C56 120.0 . . ? C54 C55 H55 120.0 . . ? C56 C55 H55 120.0 . . ? C55 C56 C51 120.0 . . ? C55 C56 H56 120.0 . . ? C51 C56 H56 120.0 . . ? C62 C61 C66 120.0 . . ? C62 C61 H61 120.0 . . ? C66 C61 H61 120.0 . . ? C63 C62 C61 120.0 . . ? C63 C62 H62 120.0 . . ? C61 C62 H62 120.0 . . ? C62 C63 C64 120.0 . . ? C62 C63 H63 120.0 . . ? C64 C63 H63 120.0 . . ? C65 C64 C63 120.0 . . ? C65 C64 H64 120.0 . . ? C63 C64 H64 120.0 . . ? C66 C65 C64 120.0 . . ? C66 C65 H65 120.0 . . ? C64 C65 H65 120.0 . . ? C65 C66 C61 120.0 . . ? C65 C66 H66 120.0 . . ? C61 C66 H66 120.0 . . ? 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 C4 O1 C5 O2 0.0 . . . . ? C4 O1 C5 C6 180.0 . . . . ? C7 C6 C5 O2 180.0 . . . . ? C7 C6 C5 O2 0.0 2_665 . . . ? C7 C6 C5 O1 0.0 . . . . ? C7 C6 C5 O1 180.0 2_665 . . . ? C7 C6 C7 C6 0.0 2_665 . . 3_565 ? C5 C6 C7 C6 180.0 . . . 3_565 ? C5 O1 C4 C3 90.6(4) . . . 10_557 ? C5 O1 C4 C3 -90.6(4) . . . . ? C3 C4 C3 C2 2.1(8) 10_557 . . . ? O1 C4 C3 C2 -176.6(4) . . . . ? C2 C1 C2 C3 -1.5(8) 10_557 . . . ? I1 C1 C2 C3 -178.4(3) . . . . ? C4 C3 C2 C1 -0.3(7) . . . . ? C56 C51 C52 C53 0.0 . . . . ? C51 C52 C53 C54 0.0 . . . . ? C52 C53 C54 C55 0.0 . . . . ? C53 C54 C55 C56 0.0 . . . . ? C54 C55 C56 C51 0.0 . . . . ? C52 C51 C56 C55 0.0 . . . . ? C66 C61 C62 C63 0.0 . . . . ? C61 C62 C63 C64 0.0 . . . . ? C62 C63 C64 C65 0.0 . . . . ? C63 C64 C65 C66 0.0 . . . . ? C64 C65 C66 C61 0.0 . . . . ? C62 C61 C66 C65 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.742 _refine_diff_density_min -0.935 _refine_diff_density_rms 0.099 # Attachment '4-IodoTMA-nonsolvated.cif' # Supplementary Material (ESI) for Chemical Communications data_new _database_code_depnum_ccdc_archive 'CCDC 688116' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzene-1,3,5-tricarboxylic acid tris-(4-iodo-phenyl) ester ; _chemical_name_common 'Benzene-1,3,5-tricarboxylic acid tris-(4-iodo-phenyl) ester' _chemical_melting_point 502.68 _chemical_formula_moiety 'C27 H15 I3 O6' _chemical_formula_sum 'C27 H15 I3 O6' _chemical_formula_weight 816.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 29.911(3) _cell_length_b 5.6474(6) _cell_length_c 31.534(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.112(5) _cell_angle_gamma 90.00 _cell_volume 5187.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 21757 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 3.655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3157 _exptl_absorpt_correction_T_max 0.8982 _exptl_absorpt_process_details 'HKL2000 Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 210(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappaCCD' _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39978 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.47 _reflns_number_total 11892 _reflns_number_gt 8033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL2000 Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' _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^)+(0.0189P)^2^+14.0015P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11892 _refine_ls_number_parameters 649 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 I5 I 0.139912(12) 1.49010(7) 0.527427(11) 0.05029(10) Uani 1 1 d . . . I2 I 0.325834(14) 1.07689(6) -0.020633(10) 0.05169(10) Uani 1 1 d . . . I4 I 0.544164(11) -0.24997(6) 0.464330(10) 0.04217(9) Uani 1 1 d . . . I1 I 0.578631(11) -0.69244(7) 0.346278(11) 0.04984(10) Uani 1 1 d . . . I6 I -0.067768(12) 0.14606(9) 0.157603(12) 0.06500(13) Uani 1 1 d . . . I3 I -0.035862(12) -0.44320(9) 0.049651(12) 0.06989(14) Uani 1 1 d . . . O10 O 0.35994(10) 0.2544(5) 0.37876(10) 0.0346(7) Uani 1 1 d . . . C10 C 0.43042(14) -0.3490(8) 0.28342(14) 0.0290(10) Uani 1 1 d . . . O6 O 0.16095(10) -0.1232(6) 0.14355(10) 0.0371(8) Uani 1 1 d . . . O12 O 0.12936(10) 0.3851(5) 0.26221(10) 0.0344(7) Uani 1 1 d . . . C16 C 0.29216(15) 0.5577(8) 0.09033(13) 0.0309(10) Uani 1 1 d . . . O5 O 0.27752(10) 0.3964(5) 0.11866(9) 0.0342(7) Uani 1 1 d . . . O9 O 0.16707(11) 0.0692(6) 0.24379(11) 0.0440(8) Uani 1 1 d . . . C35 C 0.23890(15) 0.8300(8) 0.38154(14) 0.0304(10) Uani 1 1 d . . . O4 O 0.39065(9) -0.2280(5) 0.26310(9) 0.0316(7) Uani 1 1 d . . . C25 C 0.03037(15) -0.3350(9) 0.08083(14) 0.0381(12) Uani 1 1 d . . . C3 C 0.32474(14) 0.0159(7) 0.20935(13) 0.0264(9) Uani 1 1 d . . . H3 H 0.3549 0.0745 0.2169 0.032 Uiso 1 1 calc R . . C5 C 0.24693(14) 0.0531(7) 0.16810(13) 0.0282(10) Uani 1 1 d . . . H5 H 0.2246 0.1346 0.1475 0.034 Uiso 1 1 calc R . . C42 C 0.44110(15) 0.2337(8) 0.39335(14) 0.0330(10) Uani 1 1 d . . . H42 H 0.4411 0.3766 0.3781 0.040 Uiso 1 1 calc R . . O7 O 0.33478(10) -0.0233(6) 0.32736(10) 0.0372(8) Uani 1 1 d . . . C36 C 0.16729(15) 0.2482(8) 0.26404(13) 0.0307(10) Uani 1 1 d . . . C7 C 0.34878(14) -0.3341(8) 0.25802(13) 0.0277(9) Uani 1 1 d . . . O3 O 0.17563(11) -0.4297(6) 0.19088(10) 0.0414(8) Uani 1 1 d . . . O1 O 0.34270(10) -0.5215(5) 0.27358(10) 0.0349(7) Uani 1 1 d . . . C38 C 0.39937(16) -0.0801(8) 0.41800(15) 0.0367(11) Uani 1 1 d . . . H38 H 0.3712 -0.1483 0.4197 0.044 Uiso 1 1 calc R . . C31 C 0.24127(14) 0.6309(7) 0.35116(13) 0.0273(9) Uani 1 1 d . . . C41 C 0.48215(15) 0.1259(8) 0.41324(14) 0.0338(11) Uani 1 1 d . . . H41 H 0.5103 0.1969 0.4120 0.041 Uiso 1 1 calc R . . C1 C 0.26813(14) -0.2691(8) 0.21871(13) 0.0271(9) Uani 1 1 d . . . H1 H 0.2601 -0.4059 0.2322 0.033 Uiso 1 1 calc R . . C34 C 0.32865(15) 0.1589(8) 0.34492(13) 0.0294(10) Uani 1 1 d . . . C8 C 0.30843(15) 0.3339(8) 0.15567(13) 0.0298(10) Uani 1 1 d . . . C22 C 0.11690(15) -0.2064(8) 0.12450(13) 0.0303(10) Uani 1 1 d . . . C40 C 0.48152(15) -0.0858(8) 0.43483(13) 0.0312(10) Uani 1 1 d . . . C50 C 0.06481(15) 0.4742(8) 0.20586(14) 0.0339(10) Uani 1 1 d . . . H50 H 0.0794 0.6155 0.2008 0.041 Uiso 1 1 calc R . . C17 C 0.32938(16) 0.5109(8) 0.07303(14) 0.0372(11) Uani 1 1 d . . . H17 H 0.3477 0.3767 0.0820 0.045 Uiso 1 1 calc R . . C14 C 0.50184(15) -0.3298(9) 0.33509(14) 0.0359(11) Uani 1 1 d . . . H14 H 0.5222 -0.2512 0.3578 0.043 Uiso 1 1 calc R . . O2 O 0.34507(11) 0.4279(6) 0.16739(10) 0.0390(8) Uani 1 1 d . . . C29 C 0.28645(14) 0.3056(7) 0.33445(13) 0.0267(9) Uani 1 1 d . . . C27 C 0.11092(15) -0.4155(9) 0.10135(14) 0.0358(11) Uani 1 1 d . . . H27 H 0.1362 -0.5122 0.1003 0.043 Uiso 1 1 calc R . . C49 C 0.08734(14) 0.3144(8) 0.23635(13) 0.0302(10) Uani 1 1 d . . . C4 C 0.29151(14) 0.1336(7) 0.17830(12) 0.0256(9) Uani 1 1 d . . . C2 C 0.31322(14) -0.1886(8) 0.22927(13) 0.0270(9) Uani 1 1 d . . . C53 C 0.02290(17) 0.0556(9) 0.22070(15) 0.0392(11) Uani 1 1 d . . . H53 H 0.0086 -0.0873 0.2253 0.047 Uiso 1 1 calc R . . C30 C 0.28270(15) 0.5108(7) 0.35763(13) 0.0268(9) Uani 1 1 d . . . H30 H 0.3084 0.5688 0.3779 0.032 Uiso 1 1 calc R . . C32 C 0.20346(15) 0.5512(8) 0.32009(13) 0.0295(10) Uani 1 1 d . . . H32 H 0.1754 0.6332 0.3155 0.035 Uiso 1 1 calc R . . C37 C 0.40047(14) 0.1298(8) 0.39614(14) 0.0298(10) Uani 1 1 d . . . C52 C 0.00007(15) 0.2165(9) 0.19089(14) 0.0352(11) Uani 1 1 d . . . C33 C 0.20747(14) 0.3484(8) 0.29577(13) 0.0275(9) Uani 1 1 d . . . C15 C 0.45934(15) -0.2328(8) 0.31713(14) 0.0324(10) Uani 1 1 d . . . H15 H 0.4503 -0.0893 0.3278 0.039 Uiso 1 1 calc R . . C9 C 0.18821(15) -0.2536(8) 0.17614(14) 0.0325(10) Uani 1 1 d . . . C28 C 0.24870(14) 0.2255(8) 0.30337(13) 0.0274(9) Uani 1 1 d . . . H28 H 0.2512 0.0873 0.2874 0.033 Uiso 1 1 calc R . . C6 C 0.23477(14) -0.1495(8) 0.18833(13) 0.0284(10) Uani 1 1 d . . . C19 C 0.31241(16) 0.8573(8) 0.02866(13) 0.0338(11) Uani 1 1 d . . . C13 C 0.51428(15) -0.5421(8) 0.31956(14) 0.0333(11) Uani 1 1 d . . . C26 C 0.06728(16) -0.4808(9) 0.07972(15) 0.0384(11) Uani 1 1 d . . . H26 H 0.0626 -0.6242 0.0642 0.046 Uiso 1 1 calc R . . C51 C 0.02052(15) 0.4260(9) 0.18266(14) 0.0379(11) Uani 1 1 d . . . H51 H 0.0047 0.5334 0.1618 0.045 Uiso 1 1 calc R . . C54 C 0.06697(16) 0.1034(8) 0.24404(15) 0.0372(11) Uani 1 1 d . . . H54 H 0.0828 -0.0052 0.2647 0.045 Uiso 1 1 calc R . . C21 C 0.26470(15) 0.7532(8) 0.07733(14) 0.0348(11) Uani 1 1 d . . . H21 H 0.2392 0.7835 0.0893 0.042 Uiso 1 1 calc R . . C20 C 0.27520(17) 0.9040(8) 0.04635(14) 0.0379(11) Uani 1 1 d . . . H20 H 0.2569 1.0383 0.0374 0.046 Uiso 1 1 calc R . . C39 C 0.44035(15) -0.1902(8) 0.43756(14) 0.0347(11) Uani 1 1 d . . . H39 H 0.4402 -0.3341 0.4525 0.042 Uiso 1 1 calc R . . C23 C 0.08040(17) -0.0605(9) 0.12589(15) 0.0391(11) Uani 1 1 d . . . H23 H 0.0850 0.0817 0.1418 0.047 Uiso 1 1 calc R . . C11 C 0.44233(15) -0.5605(8) 0.26733(15) 0.0349(11) Uani 1 1 d . . . H11 H 0.4220 -0.6375 0.2444 0.042 Uiso 1 1 calc R . . C18 C 0.33979(16) 0.6633(9) 0.04214(15) 0.0380(11) Uani 1 1 d . . . H18 H 0.3655 0.6341 0.0304 0.046 Uiso 1 1 calc R . . C24 C 0.03676(17) -0.1258(9) 0.10357(16) 0.0428(12) Uani 1 1 d . . . H24 H 0.0116 -0.0270 0.1040 0.051 Uiso 1 1 calc R . . C12 C 0.48460(15) -0.6574(8) 0.28547(15) 0.0358(11) Uani 1 1 d . . . H12 H 0.4934 -0.8014 0.2748 0.043 Uiso 1 1 calc R . . O11 O 0.19439(10) 0.8838(6) 0.38159(10) 0.0373(8) Uani 1 1 d . . . O8 O 0.27128(11) 0.9261(6) 0.40420(10) 0.0386(8) Uani 1 1 d . . . C46 C 0.16180(15) 1.2946(8) 0.47883(14) 0.0326(10) Uani 1 1 d . . . C43 C 0.18631(15) 1.0285(8) 0.41544(14) 0.0325(10) Uani 1 1 d . . . C44 C 0.2010(2) 0.9621(9) 0.45792(15) 0.0496(14) Uani 1 1 d . . . H44 H 0.2195 0.8272 0.4653 0.060 Uiso 1 1 calc R . . C47 C 0.14891(18) 1.3650(9) 0.43651(15) 0.0472(13) Uani 1 1 d . . . H47 H 0.1319 1.5049 0.4292 0.057 Uiso 1 1 calc R . . C48 C 0.16105(17) 1.2293(9) 0.40428(15) 0.0445(13) Uani 1 1 d . . . H48 H 0.1519 1.2753 0.3749 0.053 Uiso 1 1 calc R . . C45 C 0.1881(2) 1.0968(9) 0.49024(16) 0.0504(14) Uani 1 1 d . . . H45 H 0.1975 1.0521 0.5196 0.060 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 I5 0.0480(2) 0.0636(2) 0.04522(19) -0.02352(17) 0.02293(16) -0.01062(18) I2 0.0811(3) 0.0438(2) 0.03103(17) 0.00218(15) 0.01443(17) -0.01742(19) I4 0.03397(17) 0.0504(2) 0.03839(17) -0.00094(15) 0.00034(13) 0.00948(15) I1 0.03176(17) 0.0643(2) 0.0553(2) 0.01959(18) 0.01387(15) 0.01655(17) I6 0.0371(2) 0.1113(4) 0.0441(2) -0.0117(2) 0.00393(16) -0.0278(2) I3 0.02933(18) 0.1256(4) 0.0495(2) 0.0025(2) -0.00216(16) -0.0121(2) O10 0.0300(17) 0.0321(18) 0.0375(17) -0.0082(14) -0.0007(14) 0.0051(14) C10 0.026(2) 0.027(2) 0.035(2) 0.005(2) 0.0087(19) 0.0042(19) O6 0.0304(17) 0.0381(19) 0.0385(17) 0.0111(15) -0.0011(14) -0.0077(15) O12 0.0269(16) 0.0338(18) 0.0400(18) -0.0094(14) 0.0023(14) 0.0012(14) C16 0.030(2) 0.033(3) 0.027(2) 0.0026(19) 0.0013(19) -0.009(2) O5 0.0329(17) 0.0366(18) 0.0308(16) 0.0097(14) 0.0023(13) -0.0077(14) O9 0.0348(18) 0.042(2) 0.051(2) -0.0184(17) 0.0027(16) 0.0054(16) C35 0.034(3) 0.029(2) 0.029(2) 0.000(2) 0.009(2) 0.004(2) O4 0.0256(16) 0.0295(17) 0.0383(17) 0.0051(14) 0.0044(13) 0.0026(14) C25 0.021(2) 0.059(3) 0.030(2) 0.009(2) -0.0029(19) -0.003(2) C3 0.025(2) 0.027(2) 0.027(2) -0.0035(18) 0.0058(18) -0.0063(19) C5 0.028(2) 0.030(3) 0.026(2) -0.0005(19) 0.0053(18) 0.0017(19) C42 0.037(3) 0.026(2) 0.036(2) -0.002(2) 0.010(2) 0.003(2) O7 0.0380(18) 0.037(2) 0.0342(17) -0.0080(15) 0.0041(14) 0.0093(15) C36 0.031(2) 0.039(3) 0.022(2) 0.002(2) 0.0056(18) 0.005(2) C7 0.026(2) 0.032(3) 0.027(2) -0.0011(19) 0.0103(18) 0.002(2) O3 0.0331(18) 0.042(2) 0.0450(19) 0.0153(16) 0.0009(15) -0.0107(16) O1 0.0323(17) 0.0324(19) 0.0404(18) 0.0098(15) 0.0093(14) 0.0015(14) C38 0.031(3) 0.037(3) 0.040(3) -0.003(2) 0.006(2) -0.005(2) C31 0.031(2) 0.028(2) 0.025(2) 0.0028(18) 0.0098(18) 0.001(2) C41 0.029(2) 0.035(3) 0.039(3) -0.006(2) 0.010(2) -0.002(2) C1 0.029(2) 0.028(2) 0.025(2) -0.0013(18) 0.0101(18) -0.0022(19) C34 0.031(2) 0.030(3) 0.027(2) 0.002(2) 0.0087(19) -0.002(2) C8 0.034(2) 0.026(2) 0.029(2) 0.0000(19) 0.0049(19) -0.002(2) C22 0.029(2) 0.035(3) 0.026(2) 0.007(2) 0.0041(18) -0.007(2) C40 0.030(2) 0.034(3) 0.028(2) -0.007(2) 0.0028(19) 0.004(2) C50 0.032(2) 0.032(3) 0.038(3) 0.001(2) 0.009(2) -0.006(2) C17 0.040(3) 0.033(3) 0.038(3) 0.004(2) 0.008(2) 0.002(2) C14 0.033(3) 0.045(3) 0.027(2) 0.000(2) 0.0010(19) 0.001(2) O2 0.0334(18) 0.043(2) 0.0366(17) 0.0063(15) -0.0001(14) -0.0146(16) C29 0.030(2) 0.025(2) 0.026(2) 0.0055(18) 0.0093(18) 0.0037(19) C27 0.027(2) 0.043(3) 0.036(2) 0.001(2) 0.006(2) 0.003(2) C49 0.027(2) 0.033(3) 0.030(2) -0.009(2) 0.0046(19) -0.004(2) C4 0.030(2) 0.023(2) 0.023(2) -0.0002(17) 0.0057(18) 0.0002(19) C2 0.030(2) 0.029(2) 0.023(2) -0.0016(18) 0.0085(18) 0.0008(19) C53 0.043(3) 0.034(3) 0.041(3) -0.002(2) 0.010(2) -0.009(2) C30 0.032(2) 0.024(2) 0.024(2) -0.0013(18) 0.0069(18) -0.0027(19) C32 0.031(2) 0.028(3) 0.030(2) 0.0019(19) 0.0072(19) 0.004(2) C37 0.024(2) 0.029(3) 0.035(2) -0.005(2) 0.0044(19) 0.002(2) C52 0.025(2) 0.050(3) 0.031(2) -0.011(2) 0.0082(19) -0.012(2) C33 0.031(2) 0.029(2) 0.025(2) -0.0001(18) 0.0101(18) -0.004(2) C15 0.034(2) 0.031(3) 0.032(2) 0.000(2) 0.006(2) 0.004(2) C9 0.034(2) 0.036(3) 0.029(2) 0.001(2) 0.009(2) 0.000(2) C28 0.032(2) 0.025(2) 0.025(2) -0.0021(18) 0.0065(18) 0.0030(19) C6 0.029(2) 0.030(2) 0.028(2) -0.0009(19) 0.0089(19) -0.003(2) C19 0.043(3) 0.033(3) 0.024(2) -0.0009(19) 0.005(2) -0.005(2) C13 0.027(2) 0.040(3) 0.035(2) 0.010(2) 0.012(2) 0.008(2) C26 0.037(3) 0.039(3) 0.035(2) 0.003(2) 0.000(2) -0.005(2) C51 0.034(3) 0.050(3) 0.030(2) 0.002(2) 0.007(2) 0.001(2) C54 0.039(3) 0.036(3) 0.035(2) 0.004(2) 0.006(2) 0.001(2) C21 0.032(2) 0.041(3) 0.031(2) 0.001(2) 0.007(2) 0.000(2) C20 0.048(3) 0.030(3) 0.032(2) 0.005(2) 0.001(2) 0.003(2) C39 0.037(3) 0.030(3) 0.037(2) 0.000(2) 0.007(2) -0.001(2) C23 0.046(3) 0.035(3) 0.038(3) 0.001(2) 0.013(2) 0.002(2) C11 0.032(2) 0.029(3) 0.044(3) -0.003(2) 0.008(2) -0.002(2) C18 0.038(3) 0.043(3) 0.035(2) -0.003(2) 0.013(2) -0.005(2) C24 0.035(3) 0.051(3) 0.044(3) 0.009(3) 0.012(2) 0.010(2) C12 0.037(3) 0.028(3) 0.047(3) -0.003(2) 0.020(2) 0.004(2) O11 0.0335(18) 0.041(2) 0.0369(17) -0.0138(15) 0.0060(14) 0.0078(15) O8 0.0367(18) 0.0355(19) 0.0426(18) -0.0103(15) 0.0066(15) -0.0032(15) C46 0.031(2) 0.038(3) 0.031(2) -0.010(2) 0.0124(19) -0.006(2) C43 0.030(2) 0.034(3) 0.033(2) -0.008(2) 0.0059(19) 0.005(2) C44 0.076(4) 0.035(3) 0.033(3) 0.003(2) 0.002(3) 0.018(3) C47 0.054(3) 0.052(3) 0.034(3) -0.003(2) 0.007(2) 0.028(3) C48 0.053(3) 0.051(3) 0.030(2) 0.001(2) 0.010(2) 0.019(3) C45 0.076(4) 0.042(3) 0.030(3) 0.003(2) 0.007(3) 0.004(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 I5 C46 2.110(4) . ? I2 C19 2.097(4) . ? I4 C40 2.108(4) . ? I1 C13 2.097(4) . ? I6 C52 2.100(4) . ? I3 C25 2.093(4) . ? O10 C34 1.361(5) . ? O10 C37 1.401(5) . ? C10 C15 1.375(6) . ? C10 C11 1.376(6) . ? C10 O4 1.395(5) . ? O6 C9 1.372(5) . ? O6 C22 1.399(5) . ? O12 C36 1.363(5) . ? O12 C49 1.392(5) . ? C16 C17 1.372(6) . ? C16 C21 1.382(6) . ? C16 O5 1.413(5) . ? O5 C8 1.361(5) . ? O9 C36 1.195(5) . ? C35 O8 1.195(5) . ? C35 O11 1.366(5) . ? C35 C31 1.489(6) . ? O4 C7 1.365(5) . ? C25 C24 1.373(7) . ? C25 C26 1.384(7) . ? C3 C2 1.395(6) . ? C3 C4 1.395(6) . ? C5 C4 1.376(6) . ? C5 C6 1.398(6) . ? C42 C37 1.370(6) . ? C42 C41 1.386(6) . ? O7 C34 1.202(5) . ? C36 C33 1.490(6) . ? C7 O1 1.198(5) . ? C7 C2 1.480(6) . ? O3 C9 1.194(5) . ? C38 C37 1.376(6) . ? C38 C39 1.388(6) . ? C31 C30 1.387(6) . ? C31 C32 1.392(6) . ? C41 C40 1.378(6) . ? C1 C2 1.390(6) . ? C1 C6 1.391(6) . ? C34 C29 1.483(6) . ? C8 O2 1.198(5) . ? C8 C4 1.486(6) . ? C22 C23 1.377(6) . ? C22 C27 1.378(6) . ? C40 C39 1.385(6) . ? C50 C49 1.378(6) . ? C50 C51 1.387(6) . ? C17 C18 1.387(6) . ? C14 C13 1.378(6) . ? C14 C15 1.382(6) . ? C29 C30 1.388(6) . ? C29 C28 1.392(6) . ? C27 C26 1.379(6) . ? C49 C54 1.385(6) . ? C53 C52 1.373(7) . ? C53 C54 1.383(6) . ? C32 C33 1.399(6) . ? C52 C51 1.383(7) . ? C33 C28 1.388(6) . ? C9 C6 1.480(6) . ? C19 C18 1.376(6) . ? C19 C20 1.379(6) . ? C13 C12 1.391(6) . ? C21 C20 1.384(6) . ? C23 C24 1.385(7) . ? C11 C12 1.377(6) . ? O11 C43 1.408(5) . ? C46 C47 1.362(6) . ? C46 C45 1.367(7) . ? C43 C48 1.364(6) . ? C43 C44 1.364(6) . ? C44 C45 1.394(7) . ? C47 C48 1.385(6) . ? 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 C34 O10 C37 119.2(3) . . ? C15 C10 C11 121.9(4) . . ? C15 C10 O4 116.3(4) . . ? C11 C10 O4 121.4(4) . . ? C9 O6 C22 118.9(3) . . ? C36 O12 C49 119.6(3) . . ? C17 C16 C21 121.1(4) . . ? C17 C16 O5 121.5(4) . . ? C21 C16 O5 117.0(4) . . ? C8 O5 C16 117.5(3) . . ? O8 C35 O11 123.8(4) . . ? O8 C35 C31 125.3(4) . . ? O11 C35 C31 110.9(4) . . ? C7 O4 C10 120.2(3) . . ? C24 C25 C26 120.5(4) . . ? C24 C25 I3 120.1(4) . . ? C26 C25 I3 119.3(4) . . ? C2 C3 C4 120.1(4) . . ? C4 C5 C6 120.2(4) . . ? C37 C42 C41 119.4(4) . . ? O9 C36 O12 123.6(4) . . ? O9 C36 C33 125.9(4) . . ? O12 C36 C33 110.5(4) . . ? O1 C7 O4 124.1(4) . . ? O1 C7 C2 125.9(4) . . ? O4 C7 C2 109.9(4) . . ? C37 C38 C39 119.3(4) . . ? C30 C31 C32 120.1(4) . . ? C30 C31 C35 116.5(4) . . ? C32 C31 C35 123.2(4) . . ? C40 C41 C42 119.6(4) . . ? C2 C1 C6 120.7(4) . . ? O7 C34 O10 123.4(4) . . ? O7 C34 C29 125.9(4) . . ? O10 C34 C29 110.6(4) . . ? O2 C8 O5 123.0(4) . . ? O2 C8 C4 125.2(4) . . ? O5 C8 C4 111.7(4) . . ? C23 C22 C27 121.4(4) . . ? C23 C22 O6 117.5(4) . . ? C27 C22 O6 120.8(4) . . ? C41 C40 C39 120.8(4) . . ? C41 C40 I4 119.3(3) . . ? C39 C40 I4 119.9(3) . . ? C49 C50 C51 119.8(4) . . ? C16 C17 C18 119.4(4) . . ? C13 C14 C15 119.8(4) . . ? C30 C29 C28 119.5(4) . . ? C30 C29 C34 121.0(4) . . ? C28 C29 C34 119.2(4) . . ? C22 C27 C26 119.0(4) . . ? C50 C49 C54 121.4(4) . . ? C50 C49 O12 117.0(4) . . ? C54 C49 O12 121.2(4) . . ? C5 C4 C3 120.3(4) . . ? C5 C4 C8 123.8(4) . . ? C3 C4 C8 115.7(4) . . ? C1 C2 C3 119.2(4) . . ? C1 C2 C7 119.2(4) . . ? C3 C2 C7 121.3(4) . . ? C52 C53 C54 120.1(4) . . ? C31 C30 C29 120.5(4) . . ? C31 C32 C33 119.6(4) . . ? C42 C37 C38 121.6(4) . . ? C42 C37 O10 117.5(4) . . ? C38 C37 O10 120.8(4) . . ? C53 C52 C51 121.5(4) . . ? C53 C52 I6 119.4(3) . . ? C51 C52 I6 119.1(4) . . ? C28 C33 C32 119.9(4) . . ? C28 C33 C36 118.4(4) . . ? C32 C33 C36 121.5(4) . . ? C10 C15 C14 119.1(4) . . ? O3 C9 O6 123.5(4) . . ? O3 C9 C6 126.2(4) . . ? O6 C9 C6 110.2(4) . . ? C33 C28 C29 120.4(4) . . ? C1 C6 C5 119.4(4) . . ? C1 C6 C9 118.1(4) . . ? C5 C6 C9 122.2(4) . . ? C18 C19 C20 120.4(4) . . ? C18 C19 I2 119.9(3) . . ? C20 C19 I2 119.7(3) . . ? C14 C13 C12 120.4(4) . . ? C14 C13 I1 120.4(3) . . ? C12 C13 I1 119.2(3) . . ? C27 C26 C25 120.0(5) . . ? C52 C51 C50 118.6(4) . . ? C53 C54 C49 118.6(4) . . ? C16 C21 C20 119.1(4) . . ? C19 C20 C21 120.1(4) . . ? C40 C39 C38 119.3(4) . . ? C22 C23 C24 119.2(5) . . ? C10 C11 C12 118.8(4) . . ? C19 C18 C17 119.9(4) . . ? C25 C24 C23 119.9(5) . . ? C11 C12 C13 120.0(4) . . ? C35 O11 C43 117.7(3) . . ? C47 C46 C45 121.0(4) . . ? C47 C46 I5 119.6(3) . . ? C45 C46 I5 119.5(3) . . ? C48 C43 C44 121.2(4) . . ? C48 C43 O11 117.9(4) . . ? C44 C43 O11 120.8(4) . . ? C43 C44 C45 119.1(5) . . ? C46 C47 C48 119.6(5) . . ? C43 C48 C47 119.5(4) . . ? C46 C45 C44 119.4(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.813 _refine_diff_density_min -1.712 _refine_diff_density_rms 0.118 # Attachment '4-IodoTMA-CHCl3_complex_rev1.cif' # Supplementary Material (ESI) for Chemical Communications data_p9207 _database_code_depnum_ccdc_archive 'CCDC 688117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester chloroform solvate ; _chemical_name_common ;Benzene-1,3,5-tricarboxylic acid tris(4-iodophenyl) ester chloroform solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H15 I3 O6, 3(C H Cl3)' _chemical_formula_sum 'C30 H18 Cl9 I3 O6' _chemical_formula_weight 1174.19 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' 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 Hexagonal _symmetry_space_group_name_H-M P6~5~ loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' 'y, -x+y, z+1/6' 'x-y, x, z+5/6' _cell_length_a 16.3917(3) _cell_length_b 16.3917(3) _cell_length_c 24.8007(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5770.9(3) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9867 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.48 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.027 _exptl_crystal_density_method none _exptl_crystal_F_000 3348 _exptl_absorpt_coefficient_mu 3.103 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5355 _exptl_absorpt_correction_T_max 0.6885 _exptl_absorpt_process_details 'sadabs v2007/2' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. The C atom of one of the CHCl~3~ (C3s) was refined with EADP restrain. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 178452 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.55 _reflns_number_total 8874 _reflns_number_gt 7877 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Apex II' _computing_cell_refinement 'Bruker-Apex II' _computing_data_reduction Bruker-SAINT _computing_structure_solution 'Bruker-SHELXTL (Sheldrick, 2006)' _computing_structure_refinement 'Bruker-SHELXTL (Sheldrick, 2006)' _computing_molecular_graphics 'Bruker-SHELXTL (Sheldrick, 2006)' _computing_publication_material 'Bruker-SHELXTL (Sheldrick, 2006)' _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^)+(0.0910P)^2^+26.6917P] 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 noref _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 0.48(4) _refine_ls_number_reflns 8874 _refine_ls_number_parameters 403 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1637 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.17782(4) -0.31446(3) 0.99783(2) 0.03240(14) Uani 1 1 d . . . I2 I 1.33461(5) 0.50331(4) 1.00229(3) 0.03776(16) Uani 1 1 d . . . I3 I 0.50807(5) 0.83797(4) 1.00408(3) 0.03862(18) Uani 1 1 d . . . O1 O 0.5905(3) 0.0909(3) 1.0035(3) 0.0293(11) Uani 1 1 d . . . O2 O 0.4668(3) 0.1160(3) 0.9998(3) 0.0274(10) Uani 1 1 d . . . O3 O 0.9309(3) 0.5136(3) 1.0016(3) 0.0263(10) Uani 1 1 d . . . O4 O 0.9048(3) 0.3653(3) 1.0009(3) 0.0343(12) Uani 1 1 d . . . O5 O 0.5078(3) 0.4313(3) 1.0014(3) 0.0262(10) Uani 1 1 d . . . O6 O 0.6566(3) 0.5549(3) 1.0044(3) 0.0303(11) Uani 1 1 d . . . C1 C 0.6178(4) 0.2479(4) 1.0022(4) 0.0193(12) Uani 1 1 d . . . C2 C 0.7151(4) 0.2875(4) 1.0025(4) 0.0241(13) Uani 1 1 d . . . H2 H 0.7420 0.2479 1.0031 0.029 Uiso 1 1 calc R . . C3 C 0.7741(4) 0.3859(4) 1.0018(4) 0.0222(12) Uani 1 1 d . . . C4 C 0.7341(4) 0.4428(4) 1.0027(4) 0.0219(12) Uani 1 1 d . . . H4 H 0.7734 0.5093 1.0031 0.026 Uiso 1 1 calc R . . C5 C 0.6377(5) 0.4036(4) 1.0029(4) 0.0209(12) Uani 1 1 d . . . C6 C 0.5787(4) 0.3056(4) 1.0020(4) 0.0189(12) Uani 1 1 d . . . H6 H 0.5122 0.2790 1.0013 0.023 Uiso 1 1 calc R . . C7 C 0.5610(4) 0.1436(4) 1.0018(4) 0.0240(13) Uani 1 1 d . . . C8 C 0.4034(5) 0.0194(4) 0.9993(4) 0.0267(14) Uani 1 1 d . . . C9 C 0.3576(7) -0.0221(6) 0.9520(3) 0.041(2) Uani 1 1 d . . . H9 H 0.3709 0.0145 0.9201 0.049 Uiso 1 1 calc R . . C10 C 0.2912(7) -0.1182(6) 0.9511(4) 0.041(2) Uani 1 1 d . . . H10 H 0.2600 -0.1478 0.9185 0.050 Uiso 1 1 calc R . . C11 C 0.2718(4) -0.1690(4) 0.9978(3) 0.0212(12) Uani 1 1 d . . . C12 C 0.3176(7) -0.1279(5) 1.0447(3) 0.038(2) Uani 1 1 d . . . H12 H 0.3032 -0.1644 1.0767 0.045 Uiso 1 1 calc R . . C13 C 0.3858(6) -0.0320(6) 1.0458(4) 0.038(2) Uani 1 1 d . . . H13 H 0.4191 -0.0032 1.0781 0.045 Uiso 1 1 calc R . . C14 C 0.8786(4) 0.4309(4) 1.0011(4) 0.0251(13) Uani 1 1 d . . . C15 C 1.0010(2) 0.3973(4) 1.0001(3) 0.0296(16) Uani 1 1 d G . . C16 C 1.0470(4) 0.4037(6) 0.9518(2) 0.062(4) Uani 1 1 d G . . H16 H 1.0134 0.3889 0.9188 0.074 Uiso 1 1 calc R . . C17 C 1.1423(4) 0.4318(6) 0.9520(2) 0.070(4) Uani 1 1 d G . . H17 H 1.1738 0.4362 0.9191 0.084 Uiso 1 1 calc R . . C18 C 1.1916(2) 0.4536(4) 1.0004(3) 0.0294(15) Uani 1 1 d G . . C19 C 1.1455(4) 0.4472(6) 1.0487(2) 0.070(4) Uani 1 1 d G . . H19 H 1.1792 0.4621 1.0817 0.084 Uiso 1 1 calc R . . C20 C 1.0502(4) 0.4191(6) 1.0485(2) 0.069(4) Uani 1 1 d G . . H20 H 1.0188 0.4147 1.0814 0.082 Uiso 1 1 calc R . . C21 C 0.5926(4) 0.4624(4) 1.0025(3) 0.0181(11) Uani 1 1 d . . . C22 C 0.6224(3) 0.6162(3) 1.0042(2) 0.0289(15) Uani 1 1 d G . . C23 C 0.6205(4) 0.6600(4) 1.0518(2) 0.045(3) Uani 1 1 d G . . H23 H 0.6398 0.6451 1.0847 0.054 Uiso 1 1 calc R . . C24 C 0.5901(5) 0.7254(4) 1.0513(2) 0.048(3) Uani 1 1 d G . . H24 H 0.5888 0.7553 1.0838 0.058 Uiso 1 1 calc R . . C25 C 0.5618(3) 0.7472(3) 1.0032(3) 0.0270(14) Uani 1 1 d G . . C26 C 0.5638(4) 0.7034(4) 0.9556(2) 0.041(2) Uani 1 1 d G . . H26 H 0.5444 0.7183 0.9227 0.049 Uiso 1 1 calc R . . C27 C 0.5941(5) 0.6380(4) 0.9561(2) 0.043(2) Uani 1 1 d G . . H27 H 0.5954 0.6081 0.9235 0.051 Uiso 1 1 calc R . . C1S C 0.2505(8) 0.2312(8) 0.9856(4) 0.139(10) Uani 1 1 d D . . H1S H 0.3055 0.2967 0.9840 0.166 Uiso 1 1 calc R . . Cl1 Cl 0.2977(3) 0.1589(3) 0.9839(4) 0.155(3) Uani 1 1 d D . . Cl2 Cl 0.1944(4) 0.2251(4) 1.0446(4) 0.222(5) Uani 1 1 d D . . Cl3 Cl 0.1835(5) 0.2210(6) 0.9306(5) 0.281(7) Uani 1 1 d D . . C2S C 0.7766(9) 0.0334(4) 0.9963(5) 0.256(16) Uani 1 1 d D . . H2S H 0.7121 0.0256 0.9977 0.307 Uiso 1 1 calc R . . Cl4 Cl 0.8527(3) 0.1518(2) 0.9944(5) 0.224(5) Uani 1 1 d D . . Cl5 Cl 0.7873(3) -0.0181(3) 1.0535(4) 0.195(4) Uani 1 1 d D . . Cl6 Cl 0.7776(5) -0.0277(5) 0.9409(5) 0.258(7) Uani 1 1 d D . . Cl7 Cl 0.8139(4) -0.2268(3) 1.1734(4) 0.169(3) Uani 1 1 d D . . Cl8 Cl 0.9742(5) -0.0361(5) 1.1667(7) 0.266(7) Uani 1 1 d D . . Cl9 Cl 0.7787(7) -0.0793(8) 1.1870(5) 0.261(6) Uani 1 1 d D . . C3S C 0.8629(5) -0.1110(4) 1.1893(8) 0.256(16) Uani 1 1 d D . . H3SA H 0.8733 -0.1116 1.2290 0.307 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 0.0268(3) 0.0146(2) 0.0467(3) -0.0013(3) 0.0010(3) 0.00360(17) I2 0.0141(3) 0.0343(2) 0.0641(3) 0.0011(4) 0.0053(3) 0.0114(2) I3 0.0318(3) 0.0254(3) 0.0695(4) 0.0025(3) 0.0029(3) 0.0224(2) O1 0.025(2) 0.018(2) 0.047(3) 0.001(3) 0.000(3) 0.0122(18) O2 0.017(2) 0.0150(19) 0.052(3) 0.002(3) 0.001(3) 0.0101(17) O3 0.016(2) 0.0183(19) 0.043(3) 0.000(3) 0.002(3) 0.0073(17) O4 0.011(2) 0.017(2) 0.077(4) 0.006(3) 0.007(3) 0.0083(17) O5 0.015(2) 0.022(2) 0.045(3) 0.006(3) 0.005(3) 0.0113(17) O6 0.022(2) 0.0130(19) 0.057(3) 0.007(3) 0.003(3) 0.0091(18) C1 0.015(3) 0.018(3) 0.028(3) 0.003(3) 0.000(3) 0.010(2) C2 0.015(3) 0.020(3) 0.033(3) 0.002(4) -0.002(3) 0.006(2) C3 0.012(3) 0.021(3) 0.036(3) 0.004(3) 0.003(3) 0.010(2) C4 0.018(3) 0.014(2) 0.032(3) -0.002(3) -0.001(3) 0.007(2) C5 0.023(3) 0.015(2) 0.028(3) 0.007(3) 0.002(3) 0.012(2) C6 0.007(2) 0.020(3) 0.028(3) 0.001(3) 0.003(3) 0.005(2) C7 0.020(3) 0.020(3) 0.034(3) 0.001(3) 0.000(3) 0.011(2) C8 0.024(3) 0.014(3) 0.045(4) 0.001(4) 0.002(4) 0.011(2) C9 0.048(5) 0.024(4) 0.032(4) 0.007(3) 0.010(4) 0.005(4) C10 0.050(5) 0.021(4) 0.035(4) 0.002(3) 0.007(4) 0.005(4) C11 0.007(2) 0.019(3) 0.038(3) 0.000(3) 0.005(3) 0.006(2) C12 0.048(5) 0.016(4) 0.038(4) 0.003(3) -0.012(4) 0.008(4) C13 0.035(4) 0.017(4) 0.047(5) 0.002(3) -0.010(3) 0.003(3) C14 0.014(3) 0.022(3) 0.040(3) 0.002(4) -0.001(3) 0.009(2) C15 0.009(3) 0.017(3) 0.066(5) 0.013(4) 0.009(4) 0.009(2) C16 0.036(6) 0.112(10) 0.046(6) 0.038(6) 0.011(4) 0.043(6) C17 0.028(5) 0.124(11) 0.048(6) 0.048(6) 0.019(4) 0.031(6) C18 0.011(3) 0.015(2) 0.058(4) 0.007(4) 0.003(4) 0.003(2) C19 0.018(5) 0.123(11) 0.059(7) -0.048(7) -0.001(4) 0.028(6) C20 0.014(4) 0.114(11) 0.065(7) -0.033(7) 0.003(4) 0.022(5) C21 0.014(3) 0.014(2) 0.027(3) 0.001(3) -0.002(3) 0.008(2) C22 0.012(3) 0.016(3) 0.052(4) 0.004(4) 0.007(4) 0.002(2) C23 0.073(7) 0.053(6) 0.039(5) 0.024(4) 0.025(4) 0.054(6) C24 0.079(7) 0.052(6) 0.044(5) 0.019(4) 0.026(5) 0.056(6) C25 0.011(3) 0.018(3) 0.057(4) 0.004(4) 0.004(3) 0.011(2) C26 0.043(5) 0.037(5) 0.057(6) -0.008(4) -0.022(4) 0.030(4) C27 0.047(5) 0.043(5) 0.053(5) -0.018(4) -0.024(4) 0.033(4) C1S 0.064(9) 0.050(7) 0.30(3) 0.040(13) 0.025(14) 0.025(7) Cl1 0.075(3) 0.079(3) 0.333(9) 0.021(4) 0.027(4) 0.054(2) Cl2 0.095(4) 0.073(3) 0.507(15) 0.060(5) 0.136(7) 0.048(3) Cl3 0.102(5) 0.148(6) 0.63(2) 0.122(10) 0.041(8) 0.087(5) C2S 0.069(8) 0.103(12) 0.60(5) -0.11(2) 0.004(17) 0.044(8) Cl4 0.064(2) 0.0407(16) 0.564(16) 0.042(5) 0.062(5) 0.0229(16) Cl5 0.060(2) 0.049(2) 0.482(14) 0.020(4) 0.037(5) 0.031(2) Cl6 0.103(4) 0.081(4) 0.61(2) 0.038(8) 0.081(8) 0.057(3) Cl7 0.145(5) 0.060(3) 0.277(8) -0.012(4) 0.045(6) 0.032(3) Cl8 0.113(4) 0.110(5) 0.59(2) 0.052(9) 0.135(9) 0.064(4) Cl9 0.244(9) 0.302(12) 0.367(14) 0.080(10) 0.126(9) 0.235(10) C3S 0.069(8) 0.103(12) 0.60(5) -0.11(2) 0.004(17) 0.044(8) _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 C11 2.094(6) . ? I2 C18 2.062(3) . ? I3 C25 2.074(3) . ? O1 C7 1.182(8) . ? O2 C7 1.376(8) . ? O2 C8 1.393(7) . ? O3 C14 1.188(8) . ? O4 C14 1.343(8) . ? O4 C15 1.391(5) . ? O5 C21 1.217(7) . ? O6 C21 1.346(7) . ? O6 C22 1.374(6) . ? C1 C6 1.384(9) . ? C1 C2 1.389(8) . ? C1 C7 1.482(8) . ? C2 C3 1.405(8) . ? C2 H2 0.9500 . ? C3 C4 1.383(9) . ? C3 C14 1.488(8) . ? C4 C5 1.377(9) . ? C4 H4 0.9500 . ? C5 C6 1.400(7) . ? C5 C21 1.479(8) . ? C6 H6 0.9500 . ? C8 C13 1.372(11) . ? C8 C9 1.375(12) . ? C9 C10 1.397(11) . ? C9 H9 0.9500 . ? C10 C11 1.367(11) . ? C10 H10 0.9500 . ? C11 C12 1.367(11) . ? C12 C13 1.401(11) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C16 H16 0.9500 . ? C17 C18 1.3900 . ? C17 H17 0.9500 . ? C18 C19 1.3900 . ? C19 C20 1.3900 . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C22 C23 1.3900 . ? C22 C27 1.3900 . ? C23 C24 1.3900 . ? C23 H23 0.9500 . ? C24 C25 1.3900 . ? C24 H24 0.9500 . ? C25 C26 1.3900 . ? C26 C27 1.3900 . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C1S Cl3 1.705(5) . ? C1S Cl2 1.706(5) . ? C1S Cl1 1.709(5) . ? C1S H1S 1.0000 . ? C2S Cl4 1.704(5) . ? C2S Cl5 1.704(5) . ? C2S Cl6 1.706(5) . ? C2S H2S 1.0000 . ? Cl7 C3S 1.697(5) . ? Cl8 C3S 1.705(5) . ? Cl9 C3S 1.701(5) . ? C3S H3SA 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 C7 O2 C8 116.8(5) . . ? C14 O4 C15 117.0(5) . . ? C21 O6 C22 116.7(5) . . ? C6 C1 C2 119.8(5) . . ? C6 C1 C7 123.3(5) . . ? C2 C1 C7 116.9(6) . . ? C1 C2 C3 120.5(6) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.2(6) . . ? C4 C3 C14 118.8(5) . . ? C2 C3 C14 122.0(6) . . ? C5 C4 C3 120.4(5) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.6(6) . . ? C4 C5 C21 121.8(5) . . ? C6 C5 C21 117.6(6) . . ? C1 C6 C5 119.6(5) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 O2 124.2(6) . . ? O1 C7 C1 126.2(6) . . ? O2 C7 C1 109.5(5) . . ? C13 C8 C9 121.2(6) . . ? C13 C8 O2 119.9(8) . . ? C9 C8 O2 118.9(7) . . ? C8 C9 C10 119.8(8) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 119.1(8) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? C12 C11 C10 121.2(6) . . ? C12 C11 I1 118.1(6) . . ? C10 C11 I1 120.6(6) . . ? C11 C12 C13 120.2(7) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 118.6(8) . . ? C8 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? O3 C14 O4 125.2(6) . . ? O3 C14 C3 124.2(6) . . ? O4 C14 C3 110.6(5) . . ? C16 C15 C20 120.0 . . ? C16 C15 O4 120.8(6) . . ? C20 C15 O4 119.2(6) . . ? C17 C16 C15 120.0 . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 I2 121.4(4) . . ? C19 C18 I2 118.5(4) . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 120.0 . . ? C19 C20 H20 120.0 . . ? C15 C20 H20 120.0 . . ? O5 C21 O6 123.8(6) . . ? O5 C21 C5 124.4(5) . . ? O6 C21 C5 111.8(5) . . ? O6 C22 C23 119.8(5) . . ? O6 C22 C27 120.1(5) . . ? C23 C22 C27 120.0 . . ? C22 C23 C24 120.0 . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.0 . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.0 . . ? C24 C25 I3 119.4(4) . . ? C26 C25 I3 120.5(3) . . ? C27 C26 C25 120.0 . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C22 120.0 . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? Cl3 C1S Cl2 112.3(8) . . ? Cl3 C1S Cl1 113.9(6) . . ? Cl2 C1S Cl1 113.5(5) . . ? Cl3 C1S H1S 105.4 . . ? Cl2 C1S H1S 105.4 . . ? Cl1 C1S H1S 105.4 . . ? Cl4 C2S Cl5 112.9(6) . . ? Cl4 C2S Cl6 115.5(7) . . ? Cl5 C2S Cl6 110.2(8) . . ? Cl4 C2S H2S 105.8 . . ? Cl5 C2S H2S 105.8 . . ? Cl6 C2S H2S 105.8 . . ? Cl7 C3S Cl9 109.3(6) . . ? Cl7 C3S Cl8 117.8(6) . . ? Cl9 C3S Cl8 120.5(7) . . ? Cl7 C3S H3SA 101.8 . . ? Cl9 C3S H3SA 101.8 . . ? Cl8 C3S H3SA 101.8 . . ? 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 C6 C1 C2 C3 -0.9(16) . . . . ? C7 C1 C2 C3 178.8(8) . . . . ? C1 C2 C3 C4 2.1(17) . . . . ? C1 C2 C3 C14 -178.8(8) . . . . ? C2 C3 C4 C5 -1.4(17) . . . . ? C14 C3 C4 C5 179.4(7) . . . . ? C3 C4 C5 C6 -0.3(16) . . . . ? C3 C4 C5 C21 -178.6(7) . . . . ? C2 C1 C6 C5 -0.8(16) . . . . ? C7 C1 C6 C5 179.4(7) . . . . ? C4 C5 C6 C1 1.5(16) . . . . ? C21 C5 C6 C1 179.8(7) . . . . ? C8 O2 C7 O1 -0.8(14) . . . . ? C8 O2 C7 C1 -180.0(7) . . . . ? C6 C1 C7 O1 -177.5(10) . . . . ? C2 C1 C7 O1 2.7(14) . . . . ? C6 C1 C7 O2 1.6(12) . . . . ? C2 C1 C7 O2 -178.2(8) . . . . ? C7 O2 C8 C13 75.4(10) . . . . ? C7 O2 C8 C9 -106.5(9) . . . . ? C13 C8 C9 C10 0.4(14) . . . . ? O2 C8 C9 C10 -177.7(8) . . . . ? C8 C9 C10 C11 1.2(14) . . . . ? C9 C10 C11 C12 -1.5(13) . . . . ? C9 C10 C11 I1 -177.0(7) . . . . ? C10 C11 C12 C13 0.1(13) . . . . ? I1 C11 C12 C13 175.7(7) . . . . ? C9 C8 C13 C12 -1.8(14) . . . . ? O2 C8 C13 C12 176.3(8) . . . . ? C11 C12 C13 C8 1.6(14) . . . . ? C15 O4 C14 O3 -1.4(15) . . . . ? C15 O4 C14 C3 179.8(8) . . . . ? C4 C3 C14 O3 0.6(15) . . . . ? C2 C3 C14 O3 -178.5(10) . . . . ? C4 C3 C14 O4 179.4(9) . . . . ? C2 C3 C14 O4 0.3(13) . . . . ? C14 O4 C15 C16 -96.7(8) . . . . ? C14 O4 C15 C20 86.1(8) . . . . ? C20 C15 C16 C17 0.0 . . . . ? O4 C15 C16 C17 -177.1(5) . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C16 C17 C18 I2 -176.2(3) . . . . ? C17 C18 C19 C20 0.0 . . . . ? I2 C18 C19 C20 176.3(3) . . . . ? C18 C19 C20 C15 0.0 . . . . ? C16 C15 C20 C19 0.0 . . . . ? O4 C15 C20 C19 177.1(5) . . . . ? C22 O6 C21 O5 -0.9(12) . . . . ? C22 O6 C21 C5 179.9(7) . . . . ? C4 C5 C21 O5 178.1(9) . . . . ? C6 C5 C21 O5 -0.2(13) . . . . ? C4 C5 C21 O6 -2.7(11) . . . . ? C6 C5 C21 O6 179.0(8) . . . . ? C21 O6 C22 C23 103.4(7) . . . . ? C21 O6 C22 C27 -79.7(7) . . . . ? O6 C22 C23 C24 176.9(4) . . . . ? C27 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C23 C24 C25 I3 175.8(3) . . . . ? C24 C25 C26 C27 0.0 . . . . ? I3 C25 C26 C27 -175.7(3) . . . . ? C25 C26 C27 C22 0.0 . . . . ? O6 C22 C27 C26 -176.9(4) . . . . ? C23 C22 C27 C26 0.0 . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.850 _refine_diff_density_min -1.595 _refine_diff_density_rms 0.202