# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 #-----------------------SUBMISSION DETAILS--------------------------------# _publ_contact_author_name 'Professor F. Christopher Pigge' _publ_contact_author_address ; Department of Chemistry The University of Iowa Iowa City, 52242-1294 Iowa, USA ; _publ_contact_author_email chris-pigge@uiowa.edu _publ_requested_category ? #------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------# _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #-------------------------TITLE AND AUTHOR LIST---------------------------# _publ_section_title ; Relative importance of X...O=C versus X...X halogen bonding as structural determinants in 4-halotriaroylbenzenes ; loop_ _publ_author_name _publ_author_address 'F. Christopher Pigge' ; Department of Chemistry The University of Iowa 305 Chemistry Building Iowa City IA 52242 USA ; 'Venu R. Vangala' ; Department of Chemistry The University of Iowa 305 Chemistry Building Iowa City 52242 Iowa, USA ; 'Dale C.Swenson' ; Department of Chemistry The University of Iowa 305 Chemistry Building Iowa City 52242 Iowa, USA ; #================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 600573' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,3,5-tris(4-Bromobenzoyl)benzene _chemical_melting_point 470.49 _chemical_formula_moiety 'C27 H15 Br3 O3' _chemical_formula_sum 'C27 H15 Br3 O3' _chemical_formula_weight 627.09 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' Br Br -0.2901 2.4595 '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 8.7341(9) _cell_length_b 11.0843(11) _cell_length_c 12.6991(13) _cell_angle_alpha 95.413(5) _cell_angle_beta 98.622(5) _cell_angle_gamma 107.017(5) _cell_volume 1149.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 5054 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 5.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4666 _exptl_absorpt_correction_T_max 0.8574 _exptl_absorpt_process_details 'HKL2000 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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9937 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5256 _reflns_number_gt 3221 _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^)+(0.0515P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5256 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 O1 O 0.5459(4) 0.4076(3) 0.9068(2) 0.0450(8) Uani 1 1 d . . . O2 O 0.1351(4) -0.0687(3) 0.5781(2) 0.0413(8) Uani 1 1 d . . . O3 O 0.4031(4) 0.5944(3) 0.5640(2) 0.0415(8) Uani 1 1 d . . . Br1 Br 0.01539(6) 0.11623(5) 1.21715(4) 0.04418(16) Uani 1 1 d . . . Br2 Br 0.43103(7) -0.07016(6) 0.10884(4) 0.05520(18) Uani 1 1 d . . . Br3 Br -0.15643(6) 0.43028(5) 0.09494(4) 0.05061(17) Uani 1 1 d . . . C1 C 0.3407(5) 0.4038(4) 0.7003(3) 0.0301(10) Uani 1 1 d . . . H1 H 0.3769 0.4890 0.7364 0.036 Uiso 1 1 calc R . . C2 C 0.3382(5) 0.3045(4) 0.7592(3) 0.0317(10) Uani 1 1 d . . . C3 C 0.2875(5) 0.1795(4) 0.7058(3) 0.0308(10) Uani 1 1 d . . . H3 H 0.2796 0.1104 0.7458 0.037 Uiso 1 1 calc R . . C4 C 0.2484(5) 0.1563(4) 0.5934(3) 0.0293(9) Uani 1 1 d . . . C5 C 0.2462(5) 0.2560(4) 0.5351(3) 0.0292(9) Uani 1 1 d . . . H5 H 0.2145 0.2395 0.4589 0.035 Uiso 1 1 calc R . . C6 C 0.2908(5) 0.3805(4) 0.5888(3) 0.0277(9) Uani 1 1 d . . . C7 C 0.4077(6) 0.3346(4) 0.8785(3) 0.0323(10) Uani 1 1 d . . . C8 C 0.2109(5) 0.0212(4) 0.5387(3) 0.0308(10) Uani 1 1 d . . . C9 C 0.3016(5) 0.4914(4) 0.5281(3) 0.0301(10) Uani 1 1 d . . . C10 C 0.3089(5) 0.2766(4) 0.9571(3) 0.0298(10) Uani 1 1 d . . . C11 C 0.3843(6) 0.2953(4) 1.0644(3) 0.0385(11) Uani 1 1 d . . . H11 H 0.4971 0.3414 1.0846 0.046 Uiso 1 1 calc R . . C12 C 0.2985(6) 0.2484(4) 1.1416(3) 0.0401(12) Uani 1 1 d . . . H12 H 0.3511 0.2609 1.2146 0.048 Uiso 1 1 calc R . . C13 C 0.1332(6) 0.1824(4) 1.1108(3) 0.0353(11) Uani 1 1 d . . . C14 C 0.0556(6) 0.1642(4) 1.0051(3) 0.0388(11) Uani 1 1 d . . . H14 H -0.0577 0.1197 0.9852 0.047 Uiso 1 1 calc R . . C15 C 0.1446(6) 0.2116(4) 0.9278(3) 0.0366(11) Uani 1 1 d . . . H15 H 0.0922 0.1991 0.8547 0.044 Uiso 1 1 calc R . . C16 C 0.2709(5) 0.0000(4) 0.4362(3) 0.0299(10) Uani 1 1 d . . . C17 C 0.1919(6) -0.1127(4) 0.3661(3) 0.0354(10) Uani 1 1 d . . . H17 H 0.1040 -0.1751 0.3851 0.043 Uiso 1 1 calc R . . C18 C 0.2395(6) -0.1347(4) 0.2697(4) 0.0402(12) Uani 1 1 d . . . H18 H 0.1833 -0.2107 0.2210 0.048 Uiso 1 1 calc R . . C19 C 0.3710(6) -0.0442(5) 0.2447(3) 0.0394(11) Uani 1 1 d . . . C20 C 0.4569(5) 0.0658(4) 0.3162(4) 0.0375(11) Uani 1 1 d . . . H20 H 0.5500 0.1253 0.2999 0.045 Uiso 1 1 calc R . . C21 C 0.4047(5) 0.0867(4) 0.4109(3) 0.0324(10) Uani 1 1 d . . . H21 H 0.4618 0.1623 0.4600 0.039 Uiso 1 1 calc R . . C22 C 0.1909(5) 0.4723(4) 0.4230(3) 0.0305(10) Uani 1 1 d . . . C23 C 0.0272(5) 0.3957(4) 0.4065(3) 0.0314(10) Uani 1 1 d . . . H23 H -0.0130 0.3500 0.4614 0.038 Uiso 1 1 calc R . . C24 C -0.0751(5) 0.3871(4) 0.3100(3) 0.0335(10) Uani 1 1 d . . . H24 H -0.1874 0.3397 0.3001 0.040 Uiso 1 1 calc R . . C25 C -0.0145(6) 0.4472(4) 0.2284(3) 0.0356(10) Uani 1 1 d . . . C26 C 0.1479(5) 0.5203(4) 0.2413(4) 0.0380(11) Uani 1 1 d . . . H26 H 0.1895 0.5591 0.1836 0.046 Uiso 1 1 calc R . . C27 C 0.2469(6) 0.5350(4) 0.3395(4) 0.0378(11) Uani 1 1 d . . . H27 H 0.3563 0.5893 0.3509 0.045 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 O1 0.0408(19) 0.051(2) 0.0322(17) 0.0053(14) 0.0026(14) -0.0005(16) O2 0.053(2) 0.0342(18) 0.0335(17) 0.0084(14) 0.0156(15) 0.0037(15) O3 0.0431(19) 0.0324(18) 0.0424(18) 0.0071(14) 0.0056(15) 0.0023(15) Br1 0.0597(3) 0.0429(3) 0.0346(3) 0.0110(2) 0.0226(2) 0.0146(2) Br2 0.0681(4) 0.0800(4) 0.0322(3) 0.0084(2) 0.0194(2) 0.0405(3) Br3 0.0484(3) 0.0724(4) 0.0328(3) 0.0110(2) 0.0028(2) 0.0229(3) C1 0.030(2) 0.028(2) 0.029(2) 0.0000(18) 0.0090(18) 0.0049(18) C2 0.032(2) 0.039(3) 0.023(2) 0.0073(18) 0.0104(18) 0.006(2) C3 0.031(2) 0.032(2) 0.027(2) 0.0087(18) 0.0075(18) 0.0039(18) C4 0.031(2) 0.031(2) 0.024(2) 0.0042(17) 0.0078(18) 0.0068(19) C5 0.031(2) 0.032(2) 0.023(2) 0.0035(17) 0.0066(17) 0.0086(19) C6 0.025(2) 0.031(2) 0.029(2) 0.0082(18) 0.0079(17) 0.0092(18) C7 0.038(3) 0.031(2) 0.028(2) 0.0061(18) 0.0058(19) 0.011(2) C8 0.028(2) 0.034(2) 0.028(2) 0.0033(19) 0.0019(18) 0.008(2) C9 0.032(2) 0.029(2) 0.033(2) 0.0082(18) 0.0120(19) 0.012(2) C10 0.039(3) 0.028(2) 0.022(2) -0.0003(17) 0.0053(18) 0.0117(19) C11 0.041(3) 0.045(3) 0.027(2) 0.007(2) 0.008(2) 0.009(2) C12 0.055(3) 0.040(3) 0.023(2) 0.0070(19) 0.005(2) 0.011(2) C13 0.051(3) 0.035(3) 0.026(2) 0.0066(19) 0.016(2) 0.017(2) C14 0.035(3) 0.047(3) 0.033(2) 0.008(2) 0.011(2) 0.007(2) C15 0.041(3) 0.043(3) 0.025(2) 0.0057(19) 0.006(2) 0.013(2) C16 0.036(2) 0.029(2) 0.025(2) 0.0048(17) 0.0064(18) 0.0111(19) C17 0.041(3) 0.034(2) 0.032(2) 0.0057(19) 0.009(2) 0.011(2) C18 0.051(3) 0.037(3) 0.032(2) 0.000(2) 0.002(2) 0.017(2) C19 0.048(3) 0.051(3) 0.030(2) 0.006(2) 0.011(2) 0.028(2) C20 0.033(2) 0.046(3) 0.040(3) 0.015(2) 0.015(2) 0.015(2) C21 0.040(3) 0.032(2) 0.028(2) 0.0045(18) 0.0098(19) 0.013(2) C22 0.038(3) 0.025(2) 0.034(2) 0.0072(18) 0.0125(19) 0.015(2) C23 0.034(2) 0.026(2) 0.035(2) 0.0066(18) 0.0133(19) 0.0079(19) C24 0.032(2) 0.035(2) 0.033(2) 0.0062(19) 0.0068(19) 0.009(2) C25 0.042(3) 0.036(3) 0.033(2) 0.0068(19) 0.008(2) 0.018(2) C26 0.041(3) 0.044(3) 0.036(3) 0.017(2) 0.014(2) 0.016(2) C27 0.034(3) 0.038(3) 0.041(3) 0.012(2) 0.008(2) 0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.218(5) . ? O2 C8 1.220(5) . ? O3 C9 1.219(5) . ? Br1 C13 1.893(4) . ? Br2 C19 1.897(4) . ? Br3 C25 1.902(4) . ? C1 C2 1.385(6) . ? C1 C6 1.394(6) . ? C1 H1 0.9500 . ? C2 C3 1.396(6) . ? C2 C7 1.512(6) . ? C3 C4 1.398(5) . ? C3 H3 0.9500 . ? C4 C5 1.390(6) . ? C4 C8 1.511(6) . ? C5 C6 1.396(5) . ? C5 H5 0.9500 . ? C6 C9 1.499(6) . ? C7 C10 1.486(6) . ? C8 C16 1.498(6) . ? C9 C22 1.484(6) . ? C10 C15 1.379(6) . ? C10 C11 1.390(6) . ? C11 C12 1.371(6) . ? C11 H11 0.9500 . ? C12 C13 1.390(6) . ? C12 H12 0.9500 . ? C13 C14 1.378(6) . ? C14 C15 1.389(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.381(6) . ? C16 C17 1.389(6) . ? C17 C18 1.374(6) . ? C17 H17 0.9500 . ? C18 C19 1.386(7) . ? C18 H18 0.9500 . ? C19 C20 1.387(6) . ? C20 C21 1.372(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C27 1.393(6) . ? C22 C23 1.405(6) . ? C23 C24 1.381(6) . ? C23 H23 0.9500 . ? C24 C25 1.373(6) . ? C24 H24 0.9500 . ? C25 C26 1.389(6) . ? C26 C27 1.373(6) . ? C26 H26 0.9500 . ? C27 H27 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 C6 120.9(4) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 119.5(4) . . ? C1 C2 C7 119.2(4) . . ? C3 C2 C7 121.0(4) . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 C8 121.9(4) . . ? C3 C4 C8 117.9(4) . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.5(4) . . ? C1 C6 C9 118.9(4) . . ? C5 C6 C9 121.3(3) . . ? O1 C7 C10 122.0(4) . . ? O1 C7 C2 117.6(4) . . ? C10 C7 C2 120.4(4) . . ? O2 C8 C16 120.9(4) . . ? O2 C8 C4 120.6(4) . . ? C16 C8 C4 118.5(4) . . ? O3 C9 C22 121.0(4) . . ? O3 C9 C6 120.0(4) . . ? C22 C9 C6 119.0(3) . . ? C15 C10 C11 119.5(4) . . ? C15 C10 C7 122.2(4) . . ? C11 C10 C7 118.2(4) . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 118.7(4) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 Br1 120.2(4) . . ? C12 C13 Br1 118.7(3) . . ? C13 C14 C15 119.4(4) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C10 C15 C14 120.1(4) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C21 C16 C17 119.2(4) . . ? C21 C16 C8 122.2(4) . . ? C17 C16 C8 118.6(4) . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 118.9(4) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 121.2(4) . . ? C18 C19 Br2 119.1(3) . . ? C20 C19 Br2 119.6(4) . . ? C21 C20 C19 118.7(4) . . ? C21 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? C20 C21 C16 121.2(4) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? C27 C22 C23 118.6(4) . . ? C27 C22 C9 120.0(4) . . ? C23 C22 C9 121.4(4) . . ? C24 C23 C22 119.8(4) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 120.0(4) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 121.5(4) . . ? C24 C25 Br3 119.3(3) . . ? C26 C25 Br3 119.3(3) . . ? C27 C26 C25 118.3(4) . . ? C27 C26 H26 120.8 . . ? C25 C26 H26 120.8 . . ? C26 C27 C22 121.7(4) . . ? C26 C27 H27 119.1 . . ? C22 C27 H27 119.1 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.420 _refine_diff_density_min -0.608 _refine_diff_density_rms 0.121 #====END # End of Crystallographic Information File data_(1+2) _database_code_depnum_ccdc_archive 'CCDC 600574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (1,3,5-tris(4-Bromobenzoyl)benzene).(1,3,5-tris(4-Chlorobenzoyl)benzene) ; _chemical_name_common ;(1,3,5-tris(4-Bromobenzoyl)benzene).(1,3,5-tris(4- Chlorobenzoyl)benzene) ; _chemical_melting_point 463.55 _chemical_formula_moiety ' (C27 H15 O3 Br3)0.552, (C27 H15 O3 Cl3)0.448' _chemical_formula_sum ' C27 H15 Br1.656 Cl1.344 O3' _chemical_formula_weight 567.35 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' Br Br -0.2901 2.4595 '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 8.6566(9) _cell_length_b 11.0606(11) _cell_length_c 12.6155(13) _cell_angle_alpha 95.743(5) _cell_angle_beta 98.372(5) _cell_angle_gamma 106.709(5) _cell_volume 1131.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 4849 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'yellow orange' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 3.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5565 _exptl_absorpt_correction_T_max 0.8330 _exptl_absorpt_process_details 'HKL2000 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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9664 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5174 _reflns_number_gt 3889 _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^)+(0.0447P)^2^+0.4281P] 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 5174 _refine_ls_number_parameters 308 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.049 _refine_ls_shift/su_mean 0.002 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 O1 O 0.5451(2) 0.40742(18) 0.90667(15) 0.0442(5) Uani 1 1 d . . . O2 O 0.1345(2) -0.06933(16) 0.57613(15) 0.0412(5) Uani 1 1 d . . . O3 O 0.4004(2) 0.59387(16) 0.56213(16) 0.0409(5) Uani 1 1 d . . . Br1 Br 0.0096(4) 0.1132(4) 1.2188(3) 0.0398(3) Uani 0.552(3) 1 d PD . . Br2 Br 0.4404(4) -0.0651(2) 0.1050(2) 0.0486(3) Uani 0.552(3) 1 d PD . . Br3 Br -0.1578(4) 0.4336(2) 0.0920(2) 0.0434(3) Uani 0.552(3) 1 d PD . . Cl1 Cl 0.0315(15) 0.1208(12) 1.2130(10) 0.0398(3) Uani 0.448(3) 1 d PD . . Cl2 Cl 0.4229(13) -0.0860(8) 0.1142(7) 0.0486(3) Uani 0.448(3) 1 d PD . . Cl3 Cl -0.1540(13) 0.4125(8) 0.0980(8) 0.0434(3) Uani 0.448(3) 1 d PD . . C1 C 0.3390(3) 0.4033(2) 0.6992(2) 0.0314(5) Uani 1 1 d . . . H1 H 0.3757 0.4887 0.7356 0.038 Uiso 1 1 calc R . . C2 C 0.3364(3) 0.3036(2) 0.7586(2) 0.0305(5) Uani 1 1 d . . . C3 C 0.2862(3) 0.1789(2) 0.7048(2) 0.0308(5) Uani 1 1 d . . . H3 H 0.2780 0.1099 0.7450 0.037 Uiso 1 1 calc R . . C4 C 0.2479(3) 0.1549(2) 0.59183(19) 0.0279(5) Uani 1 1 d . . . C5 C 0.2451(3) 0.2548(2) 0.5329(2) 0.0282(5) Uani 1 1 d . . . H5 H 0.2137 0.2382 0.4562 0.034 Uiso 1 1 calc R . . C6 C 0.2889(3) 0.3797(2) 0.5877(2) 0.0286(5) Uani 1 1 d . . . C7 C 0.4058(3) 0.3343(2) 0.8783(2) 0.0333(5) Uani 1 1 d . . . C8 C 0.2106(3) 0.0203(2) 0.5362(2) 0.0306(5) Uani 1 1 d . . . C9 C 0.2995(3) 0.4901(2) 0.5256(2) 0.0305(5) Uani 1 1 d . . . C10 C 0.3073(3) 0.2774(2) 0.9579(2) 0.0313(5) Uani 1 1 d . . . C11 C 0.3829(3) 0.2948(3) 1.0657(2) 0.0396(6) Uani 1 1 d . . . H11 H 0.4967 0.3398 1.0861 0.048 Uiso 1 1 calc R . . C12 C 0.2958(3) 0.2479(2) 1.1433(2) 0.0408(6) Uani 1 1 d . . . H12 H 0.3482 0.2611 1.2169 0.049 Uiso 1 1 calc R . . C13 C 0.1313(3) 0.1813(2) 1.1127(2) 0.0362(6) Uani 1 1 d D . . C14 C 0.0516(3) 0.1630(3) 1.0064(2) 0.0407(6) Uani 1 1 d . . . H14 H -0.0623 0.1180 0.9866 0.049 Uiso 1 1 calc R . . C15 C 0.1412(3) 0.2115(3) 0.9288(2) 0.0371(6) Uani 1 1 d . . . H15 H 0.0883 0.1994 0.8554 0.044 Uiso 1 1 calc R . . C16 C 0.2716(3) -0.0010(2) 0.4338(2) 0.0303(5) Uani 1 1 d . . . C17 C 0.1938(3) -0.1138(2) 0.3626(2) 0.0354(6) Uani 1 1 d . . . H17 H 0.1047 -0.1762 0.3809 0.042 Uiso 1 1 calc R . . C18 C 0.2444(3) -0.1362(3) 0.2657(2) 0.0409(6) Uani 1 1 d . . . H18 H 0.1894 -0.2127 0.2167 0.049 Uiso 1 1 calc R . . C19 C 0.3766(3) -0.0455(3) 0.2409(2) 0.0389(6) Uani 1 1 d D . . C20 C 0.4614(3) 0.0639(3) 0.3125(2) 0.0382(6) Uani 1 1 d . . . H20 H 0.5553 0.1230 0.2961 0.046 Uiso 1 1 calc R . . C21 C 0.4081(3) 0.0865(2) 0.4089(2) 0.0326(5) Uani 1 1 d . . . H21 H 0.4651 0.1622 0.4584 0.039 Uiso 1 1 calc R . . C22 C 0.1874(3) 0.4708(2) 0.4201(2) 0.0300(5) Uani 1 1 d . . . C23 C 0.0244(3) 0.3943(2) 0.4032(2) 0.0321(5) Uani 1 1 d . . . H23 H -0.0155 0.3490 0.4587 0.039 Uiso 1 1 calc R . . C24 C -0.0793(3) 0.3840(2) 0.3064(2) 0.0357(6) Uani 1 1 d . . . H24 H -0.1918 0.3354 0.2965 0.043 Uiso 1 1 calc R . . C25 C -0.0182(3) 0.4451(2) 0.2240(2) 0.0355(6) Uani 1 1 d D . . C26 C 0.1446(3) 0.5191(2) 0.2378(2) 0.0396(6) Uani 1 1 d . . . H26 H 0.1860 0.5591 0.1801 0.048 Uiso 1 1 calc R . . C27 C 0.2454(3) 0.5337(2) 0.3365(2) 0.0378(6) Uani 1 1 d . . . H27 H 0.3558 0.5872 0.3478 0.045 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 O1 0.0405(10) 0.0492(11) 0.0332(11) 0.0072(9) 0.0037(8) -0.0003(9) O2 0.0528(11) 0.0315(9) 0.0379(11) 0.0104(8) 0.0168(9) 0.0047(8) O3 0.0439(10) 0.0302(10) 0.0413(11) 0.0057(8) 0.0040(9) 0.0020(8) Br1 0.0524(11) 0.0373(5) 0.0340(5) 0.0110(3) 0.0231(5) 0.0111(6) Br2 0.0613(8) 0.0670(10) 0.0321(6) 0.0125(5) 0.0212(3) 0.0344(7) Br3 0.0451(3) 0.0576(10) 0.0319(4) 0.0133(5) 0.0019(3) 0.0227(6) Cl1 0.0524(11) 0.0373(5) 0.0340(5) 0.0110(3) 0.0231(5) 0.0111(6) Cl2 0.0613(8) 0.0670(10) 0.0321(6) 0.0125(5) 0.0212(3) 0.0344(7) Cl3 0.0451(3) 0.0576(10) 0.0319(4) 0.0133(5) 0.0019(3) 0.0227(6) C1 0.0319(12) 0.0311(12) 0.0295(14) 0.0016(10) 0.0071(10) 0.0071(10) C2 0.0300(12) 0.0351(13) 0.0257(13) 0.0051(10) 0.0072(10) 0.0078(10) C3 0.0314(12) 0.0334(13) 0.0286(13) 0.0084(10) 0.0084(10) 0.0088(10) C4 0.0282(11) 0.0304(12) 0.0251(13) 0.0041(10) 0.0064(9) 0.0084(9) C5 0.0285(11) 0.0323(13) 0.0247(12) 0.0075(10) 0.0052(10) 0.0096(9) C6 0.0268(11) 0.0303(12) 0.0296(13) 0.0058(10) 0.0074(10) 0.0087(9) C7 0.0374(13) 0.0329(13) 0.0284(14) 0.0046(10) 0.0058(11) 0.0088(11) C8 0.0314(12) 0.0311(12) 0.0291(13) 0.0083(10) 0.0044(10) 0.0086(10) C9 0.0308(12) 0.0309(13) 0.0335(14) 0.0070(10) 0.0120(10) 0.0114(10) C10 0.0397(13) 0.0291(12) 0.0239(13) 0.0011(10) 0.0027(10) 0.0110(10) C11 0.0425(14) 0.0402(14) 0.0336(15) 0.0071(12) 0.0051(12) 0.0092(11) C12 0.0528(16) 0.0406(15) 0.0274(14) 0.0061(12) 0.0043(12) 0.0134(12) C13 0.0510(15) 0.0308(13) 0.0314(15) 0.0068(11) 0.0159(12) 0.0149(11) C14 0.0390(14) 0.0450(15) 0.0367(16) 0.0078(12) 0.0105(12) 0.0087(11) C15 0.0373(13) 0.0463(15) 0.0256(14) 0.0047(11) 0.0023(11) 0.0115(11) C16 0.0329(12) 0.0303(12) 0.0299(14) 0.0087(10) 0.0046(10) 0.0123(10) C17 0.0401(14) 0.0292(13) 0.0365(15) 0.0052(11) 0.0079(11) 0.0094(10) C18 0.0520(16) 0.0346(14) 0.0361(16) -0.0003(12) 0.0044(12) 0.0173(12) C19 0.0458(15) 0.0484(16) 0.0302(14) 0.0063(12) 0.0082(12) 0.0257(13) C20 0.0376(13) 0.0435(15) 0.0390(16) 0.0132(12) 0.0140(12) 0.0150(11) C21 0.0339(12) 0.0314(13) 0.0328(14) 0.0050(11) 0.0067(11) 0.0103(10) C22 0.0333(12) 0.0270(12) 0.0331(14) 0.0064(10) 0.0101(10) 0.0119(10) C23 0.0337(12) 0.0311(12) 0.0343(14) 0.0098(11) 0.0117(11) 0.0101(10) C24 0.0305(12) 0.0347(13) 0.0422(16) 0.0087(12) 0.0076(11) 0.0092(10) C25 0.0367(13) 0.0403(14) 0.0335(15) 0.0074(11) 0.0060(11) 0.0177(11) C26 0.0445(15) 0.0428(15) 0.0376(16) 0.0177(12) 0.0142(12) 0.0156(12) C27 0.0334(13) 0.0391(14) 0.0428(16) 0.0152(12) 0.0120(12) 0.0085(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 O1 C7 1.221(3) . ? O2 C8 1.221(3) . ? O3 C9 1.222(3) . ? Br1 C13 1.904(3) . ? Br2 C19 1.887(4) . ? Br3 C25 1.880(4) . ? Cl1 C13 1.718(9) . ? Cl2 C19 1.750(8) . ? Cl3 C25 1.772(10) . ? C1 C6 1.386(3) . ? C1 C2 1.390(3) . ? C1 H1 0.9500 . ? C2 C3 1.391(3) . ? C2 C7 1.507(4) . ? C3 C4 1.395(3) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 C8 1.504(3) . ? C5 C6 1.401(3) . ? C5 H5 0.9500 . ? C6 C9 1.503(3) . ? C7 C10 1.483(3) . ? C8 C16 1.488(3) . ? C9 C22 1.485(4) . ? C10 C15 1.386(4) . ? C10 C11 1.390(4) . ? C11 C12 1.374(4) . ? C11 H11 0.9500 . ? C12 C13 1.379(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C14 C15 1.391(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.390(4) . ? C16 C21 1.394(3) . ? C17 C18 1.381(4) . ? C17 H17 0.9500 . ? C18 C19 1.385(4) . ? C18 H18 0.9500 . ? C19 C20 1.377(4) . ? C20 C21 1.387(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.394(3) . ? C22 C27 1.396(3) . ? C23 C24 1.380(4) . ? C23 H23 0.9500 . ? C24 C25 1.383(4) . ? C24 H24 0.9500 . ? C25 C26 1.387(4) . ? C26 C27 1.379(4) . ? C26 H26 0.9500 . ? C27 H27 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 C6 C1 C2 120.9(2) . . ? C6 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.4(2) . . ? C1 C2 C7 119.0(2) . . ? C3 C2 C7 121.3(2) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 C8 118.6(2) . . ? C5 C4 C8 121.4(2) . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 119.7(2) . . ? C1 C6 C9 119.5(2) . . ? C5 C6 C9 120.5(2) . . ? O1 C7 C10 121.7(2) . . ? O1 C7 C2 117.5(2) . . ? C10 C7 C2 120.8(2) . . ? O2 C8 C16 121.0(2) . . ? O2 C8 C4 120.2(2) . . ? C16 C8 C4 118.7(2) . . ? O3 C9 C22 121.0(2) . . ? O3 C9 C6 119.7(2) . . ? C22 C9 C6 119.3(2) . . ? C15 C10 C11 119.1(2) . . ? C15 C10 C7 122.1(2) . . ? C11 C10 C7 118.7(2) . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.0(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 Cl1 116.6(5) . . ? C14 C13 Cl1 121.9(5) . . ? C12 C13 Br1 119.6(2) . . ? C14 C13 Br1 118.9(2) . . ? C13 C14 C15 118.7(2) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C10 C15 C14 120.5(3) . . ? C10 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C21 119.0(2) . . ? C17 C16 C8 119.0(2) . . ? C21 C16 C8 122.0(2) . . ? C18 C17 C16 120.8(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C20 C19 C18 121.3(2) . . ? C20 C19 Cl2 125.0(4) . . ? C18 C19 Cl2 113.7(4) . . ? C20 C19 Br2 117.8(2) . . ? C18 C19 Br2 120.8(2) . . ? C19 C20 C21 119.2(2) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C20 C21 C16 120.5(2) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? C23 C22 C27 119.0(2) . . ? C23 C22 C9 121.7(2) . . ? C27 C22 C9 119.2(2) . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C24 C25 C26 121.2(2) . . ? C24 C25 Cl3 116.3(4) . . ? C26 C25 Cl3 122.3(4) . . ? C24 C25 Br3 120.1(2) . . ? C26 C25 Br3 118.6(2) . . ? C27 C26 C25 118.9(2) . . ? C27 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? C26 C27 C22 120.9(2) . . ? C26 C27 H27 119.5 . . ? C22 C27 H27 119.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.417 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.069 #====END # End of Crystallographic Information File data_3 _database_code_depnum_ccdc_archive 'CCDC 600575' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5-tris(4-Iodobenzoyl)benzene ; _chemical_name_common 1,3,5-tris(4-Iodobenzoyl)benzene _chemical_melting_point 484.29 _chemical_formula_moiety 'C27 H15 I3 O3' _chemical_formula_sum 'C27 H15 I3 O3' _chemical_formula_weight 768.09 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 7.3649(7) _cell_length_b 13.8815(13) _cell_length_c 24.580(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.966(5) _cell_angle_gamma 90.00 _cell_volume 2509.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 11009 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'orange yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.033 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 3.763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4412 _exptl_absorpt_correction_T_max 0.9375 _exptl_absorpt_process_details 'HKL2000 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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20899 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5758 _reflns_number_gt 4354 _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^)+(0.0447P)^2^+1.2578P] 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 5758 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 O1 O 0.1095(4) 1.03588(17) 0.60223(10) 0.0441(7) Uani 1 1 d . . . O2 O 0.4486(4) 0.63239(17) 0.54490(10) 0.0383(6) Uani 1 1 d . . . O3 O 0.3076(3) 1.09073(16) 0.42705(10) 0.0321(6) Uani 1 1 d . . . I1 I -0.19968(4) 0.72438(2) 0.798216(12) 0.05238(11) Uani 1 1 d . . . I2 I 1.22925(4) 0.59689(2) 0.394650(11) 0.04395(9) Uani 1 1 d . . . I3 I 0.41294(4) 0.90678(2) 0.166881(10) 0.04682(10) Uani 1 1 d . . . C1 C 0.2255(4) 0.9626(2) 0.50677(13) 0.0260(7) Uani 1 1 d . . . H1 H 0.1634 1.0226 0.5056 0.031 Uiso 1 1 calc R . . C2 C 0.2193(5) 0.9059(2) 0.55318(14) 0.0263(7) Uani 1 1 d . . . C3 C 0.3113(4) 0.8178(2) 0.55462(13) 0.0253(7) Uani 1 1 d . . . H3 H 0.3062 0.7774 0.5857 0.030 Uiso 1 1 calc R . . C4 C 0.4106(4) 0.7890(2) 0.51075(13) 0.0247(7) Uani 1 1 d . . . C5 C 0.4154(4) 0.8465(2) 0.46438(13) 0.0251(7) Uani 1 1 d . . . H5 H 0.4831 0.8265 0.4345 0.030 Uiso 1 1 calc R . . C6 C 0.3202(4) 0.9338(2) 0.46198(13) 0.0248(7) Uani 1 1 d . . . C7 C 0.1298(5) 0.9490(3) 0.60098(14) 0.0308(8) Uani 1 1 d . . . C8 C 0.5085(5) 0.6944(2) 0.51612(13) 0.0275(7) Uani 1 1 d . . . C9 C 0.3274(4) 1.0050(2) 0.41631(13) 0.0265(7) Uani 1 1 d . . . C10 C 0.0653(5) 0.8887(2) 0.64649(14) 0.0280(7) Uani 1 1 d . . . C11 C 0.0617(5) 0.9327(3) 0.69753(14) 0.0332(8) Uani 1 1 d . . . H11 H 0.1100 0.9957 0.7026 0.040 Uiso 1 1 calc R . . C12 C -0.0118(5) 0.8851(3) 0.74095(15) 0.0359(8) Uani 1 1 d . . . H12 H -0.0134 0.9149 0.7757 0.043 Uiso 1 1 calc R . . C13 C -0.0827(5) 0.7936(3) 0.73275(15) 0.0338(8) Uani 1 1 d . . . C14 C -0.0806(5) 0.7491(3) 0.68224(17) 0.0375(9) Uani 1 1 d . . . H14 H -0.1302 0.6864 0.6772 0.045 Uiso 1 1 calc R . . C15 C -0.0060(5) 0.7967(3) 0.63926(15) 0.0325(8) Uani 1 1 d . . . H15 H -0.0035 0.7663 0.6047 0.039 Uiso 1 1 calc R . . C16 C 0.6779(4) 0.6761(2) 0.48639(13) 0.0266(7) Uani 1 1 d . . . C17 C 0.7163(5) 0.5807(2) 0.47237(15) 0.0349(9) Uani 1 1 d . . . H17 H 0.6344 0.5306 0.4808 0.042 Uiso 1 1 calc R . . C18 C 0.8728(5) 0.5593(3) 0.44626(16) 0.0367(9) Uani 1 1 d . . . H18 H 0.8978 0.4949 0.4360 0.044 Uiso 1 1 calc R . . C19 C 0.9924(5) 0.6323(3) 0.43520(14) 0.0324(8) Uani 1 1 d . . . C20 C 0.9587(5) 0.7267(2) 0.44900(15) 0.0330(8) Uani 1 1 d . . . H20 H 1.0427 0.7761 0.4411 0.040 Uiso 1 1 calc R . . C21 C 0.8003(5) 0.7482(3) 0.47456(14) 0.0316(8) Uani 1 1 d . . . H21 H 0.7753 0.8130 0.4841 0.038 Uiso 1 1 calc R . . C22 C 0.3584(5) 0.9755(2) 0.35957(13) 0.0272(7) Uani 1 1 d . . . C23 C 0.2971(5) 0.8879(2) 0.33783(14) 0.0305(8) Uani 1 1 d . . . H23 H 0.2453 0.8414 0.3608 0.037 Uiso 1 1 calc R . . C24 C 0.3113(5) 0.8684(3) 0.28308(15) 0.0345(8) Uani 1 1 d . . . H24 H 0.2671 0.8092 0.2683 0.041 Uiso 1 1 calc R . . C25 C 0.3903(5) 0.9358(3) 0.24963(14) 0.0334(8) Uani 1 1 d . . . C26 C 0.4529(5) 1.0230(3) 0.27055(15) 0.0356(8) Uani 1 1 d . . . H26 H 0.5067 1.0688 0.2476 0.043 Uiso 1 1 calc R . . C27 C 0.4365(5) 1.0427(3) 0.32529(14) 0.0311(8) Uani 1 1 d . . . H27 H 0.4787 1.1026 0.3398 0.037 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 O1 0.071(2) 0.0258(14) 0.0380(15) 0.0007(11) 0.0224(14) 0.0082(13) O2 0.0536(17) 0.0282(12) 0.0346(14) 0.0040(11) 0.0184(12) 0.0023(12) O3 0.0397(15) 0.0268(13) 0.0298(13) 0.0008(10) 0.0033(11) 0.0014(11) I1 0.0569(2) 0.05747(19) 0.04433(18) 0.01379(13) 0.01775(14) -0.00691(14) I2 0.03341(15) 0.05749(19) 0.04164(17) -0.00818(12) 0.00868(11) 0.00953(12) I3 0.05357(19) 0.06179(19) 0.02594(14) -0.00443(11) 0.01026(12) -0.00981(13) C1 0.0252(17) 0.0235(16) 0.0294(18) 0.0004(13) 0.0020(14) -0.0007(14) C2 0.0251(17) 0.0279(17) 0.0263(17) -0.0023(13) 0.0048(14) -0.0014(14) C3 0.0285(18) 0.0229(16) 0.0248(17) 0.0013(13) 0.0052(13) -0.0012(14) C4 0.0217(16) 0.0244(16) 0.0280(17) -0.0007(13) 0.0019(13) -0.0017(13) C5 0.0234(17) 0.0282(17) 0.0241(16) -0.0041(13) 0.0037(13) -0.0027(14) C6 0.0243(17) 0.0238(16) 0.0262(17) -0.0017(13) -0.0006(13) -0.0012(13) C7 0.0312(19) 0.0316(19) 0.0299(19) -0.0002(15) 0.0035(15) -0.0001(15) C8 0.037(2) 0.0230(16) 0.0223(17) -0.0034(13) 0.0037(14) -0.0019(15) C9 0.0227(17) 0.0279(18) 0.0288(18) -0.0005(14) 0.0018(14) 0.0003(14) C10 0.0258(17) 0.0299(18) 0.0287(18) 0.0012(14) 0.0055(14) 0.0022(14) C11 0.037(2) 0.0345(19) 0.0283(19) -0.0013(15) 0.0049(16) 0.0008(16) C12 0.036(2) 0.044(2) 0.0281(19) -0.0002(16) 0.0050(16) 0.0043(17) C13 0.0276(19) 0.042(2) 0.032(2) 0.0107(16) 0.0055(15) 0.0011(16) C14 0.036(2) 0.034(2) 0.043(2) 0.0035(17) 0.0073(17) -0.0008(16) C15 0.032(2) 0.0348(19) 0.0308(19) -0.0019(15) 0.0063(15) 0.0040(16) C16 0.0276(18) 0.0263(17) 0.0259(17) -0.0015(13) 0.0015(14) 0.0037(14) C17 0.036(2) 0.0253(18) 0.044(2) 0.0027(15) 0.0081(18) 0.0025(15) C18 0.037(2) 0.0275(18) 0.046(2) -0.0066(16) 0.0073(18) 0.0061(16) C19 0.0273(18) 0.042(2) 0.0278(18) -0.0022(15) 0.0014(14) 0.0074(16) C20 0.0289(19) 0.0282(18) 0.042(2) -0.0005(15) 0.0057(16) 0.0005(15) C21 0.034(2) 0.0247(17) 0.036(2) -0.0026(14) 0.0014(16) 0.0025(15) C22 0.0261(17) 0.0288(17) 0.0266(17) 0.0003(14) 0.0003(13) 0.0002(14) C23 0.034(2) 0.0313(19) 0.0269(18) 0.0025(14) 0.0057(15) -0.0023(15) C24 0.035(2) 0.0363(19) 0.0325(19) -0.0036(16) 0.0054(16) -0.0043(17) C25 0.0304(19) 0.048(2) 0.0222(17) -0.0013(15) 0.0032(14) -0.0017(17) C26 0.037(2) 0.041(2) 0.0289(19) 0.0071(16) 0.0055(16) -0.0055(17) C27 0.0320(19) 0.0297(18) 0.0316(19) 0.0014(14) 0.0021(15) -0.0052(15) _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 O1 C7 1.216(4) . ? O2 C8 1.212(4) . ? O3 C9 1.230(4) . ? I1 C13 2.097(3) . ? I2 C19 2.111(3) . ? I3 C25 2.089(3) . ? C1 C2 1.389(5) . ? C1 C6 1.392(5) . ? C1 H1 0.9500 . ? C2 C3 1.397(4) . ? C2 C7 1.502(5) . ? C3 C4 1.393(4) . ? C3 H3 0.9500 . ? C4 C5 1.393(5) . ? C4 C8 1.501(5) . ? C5 C6 1.400(5) . ? C5 H5 0.9500 . ? C6 C9 1.498(5) . ? C7 C10 1.494(5) . ? C8 C16 1.500(5) . ? C9 C22 1.482(5) . ? C10 C15 1.389(5) . ? C10 C11 1.397(5) . ? C11 C12 1.389(5) . ? C11 H11 0.9500 . ? C12 C13 1.385(5) . ? C12 H12 0.9500 . ? C13 C14 1.387(6) . ? C14 C15 1.383(5) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.387(5) . ? C16 C17 1.401(5) . ? C17 C18 1.380(5) . ? C17 H17 0.9500 . ? C18 C19 1.379(5) . ? C18 H18 0.9500 . ? C19 C20 1.379(5) . ? C20 C21 1.386(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.394(5) . ? C22 C27 1.400(5) . ? C23 C24 1.382(5) . ? C23 H23 0.9500 . ? C24 C25 1.392(5) . ? C24 H24 0.9500 . ? C25 C26 1.384(5) . ? C26 C27 1.384(5) . ? C26 H26 0.9500 . ? C27 H27 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 C6 121.8(3) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 118.7(3) . . ? C1 C2 C7 116.8(3) . . ? C3 C2 C7 124.1(3) . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 C8 116.9(3) . . ? C5 C4 C8 122.8(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.0(3) . . ? C1 C6 C9 116.3(3) . . ? C5 C6 C9 124.4(3) . . ? O1 C7 C10 119.5(3) . . ? O1 C7 C2 118.4(3) . . ? C10 C7 C2 122.1(3) . . ? O2 C8 C16 120.1(3) . . ? O2 C8 C4 119.0(3) . . ? C16 C8 C4 120.9(3) . . ? O3 C9 C22 119.6(3) . . ? O3 C9 C6 117.9(3) . . ? C22 C9 C6 122.5(3) . . ? C15 C10 C11 119.5(3) . . ? C15 C10 C7 123.5(3) . . ? C11 C10 C7 116.7(3) . . ? C12 C11 C10 120.6(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.1(3) . . ? C12 C13 I1 118.4(3) . . ? C14 C13 I1 120.5(3) . . ? C15 C14 C13 119.6(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C10 120.2(3) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? C21 C16 C17 119.3(3) . . ? C21 C16 C8 123.1(3) . . ? C17 C16 C8 117.6(3) . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.4(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 121.6(3) . . ? C18 C19 I2 118.3(3) . . ? C20 C19 I2 120.0(3) . . ? C19 C20 C21 118.9(3) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C20 C21 C16 120.7(3) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C23 C22 C27 119.1(3) . . ? C23 C22 C9 122.6(3) . . ? C27 C22 C9 118.1(3) . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.6(3) . . ? C26 C25 I3 119.2(3) . . ? C24 C25 I3 120.2(3) . . ? C27 C26 C25 119.3(3) . . ? C27 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? C26 C27 C22 120.8(3) . . ? C26 C27 H27 119.6 . . ? C22 C27 H27 119.6 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.068 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.129 #====END # End of Crystallographic Information File data_4 _database_code_depnum_ccdc_archive 'CCDC 600576' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,5-tris(4-Fluorobenzoyl)benzene ; _chemical_name_common 1,3,5-tris(4-Fluorobenzoyl)benzene _chemical_melting_point 457.77 _chemical_formula_moiety 'C27 H15 F3 O3' _chemical_formula_sum 'C27 H15 F3 O3' _chemical_formula_weight 444.39 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' F F 0.0171 0.0103 '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 22.757(2) _cell_length_b 8.7286(9) _cell_length_c 10.5930(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.174(5) _cell_angle_gamma 90.00 _cell_volume 2064.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 7244 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'HKL2000 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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15622 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 27.43 _reflns_number_total 4691 _reflns_number_gt 3469 _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^)+(0.0673P)^2^+0.1636P] 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 4691 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 O1 O 0.36737(4) 0.64085(11) 0.39831(9) 0.0335(2) Uani 1 1 d . . . O2 O 0.36206(4) 0.52691(12) 0.99526(9) 0.0347(2) Uani 1 1 d . . . O3 O 0.19454(5) 0.28573(13) 0.40442(10) 0.0423(3) Uani 1 1 d . . . F1 F 0.62768(4) 0.69626(11) 0.72276(10) 0.0507(3) Uani 1 1 d . . . F2 F 0.11100(4) 0.64715(13) 1.14414(10) 0.0571(3) Uani 1 1 d . . . F3 F -0.02977(5) 0.34629(19) 0.66248(14) 0.0888(4) Uani 1 1 d . . . C1 C 0.29010(6) 0.47414(15) 0.52106(13) 0.0265(3) Uani 1 1 d . . . H1 H 0.2857 0.4581 0.4310 0.032 Uiso 1 1 calc R . . C2 C 0.34118(6) 0.54807(14) 0.58783(12) 0.0251(3) Uani 1 1 d . . . C3 C 0.34738(6) 0.57117(15) 0.72025(13) 0.0260(3) Uani 1 1 d . . . H3 H 0.3817 0.6225 0.7664 0.031 Uiso 1 1 calc R . . C4 C 0.30344(6) 0.51930(15) 0.78482(12) 0.0246(3) Uani 1 1 d . . . C5 C 0.25290(6) 0.44498(14) 0.71715(13) 0.0258(3) Uani 1 1 d . . . H5 H 0.2232 0.4085 0.7616 0.031 Uiso 1 1 calc R . . C6 C 0.24553(6) 0.42369(15) 0.58406(12) 0.0254(3) Uani 1 1 d . . . C7 C 0.38494(6) 0.60961(15) 0.51154(12) 0.0256(3) Uani 1 1 d . . . C8 C 0.31244(6) 0.53907(15) 0.92794(12) 0.0259(3) Uani 1 1 d . . . C9 C 0.19120(6) 0.34807(16) 0.50588(13) 0.0288(3) Uani 1 1 d . . . C10 C 0.44905(6) 0.63273(15) 0.57379(12) 0.0255(3) Uani 1 1 d . . . C11 C 0.48174(6) 0.74459(16) 0.52333(13) 0.0306(3) Uani 1 1 d . . . H11 H 0.4625 0.8060 0.4533 0.037 Uiso 1 1 calc R . . C12 C 0.54173(6) 0.76696(17) 0.57402(15) 0.0343(3) Uani 1 1 d . . . H12 H 0.5639 0.8441 0.5406 0.041 Uiso 1 1 calc R . . C13 C 0.56852(6) 0.67493(17) 0.67395(14) 0.0327(3) Uani 1 1 d . . . C14 C 0.53869(6) 0.56148(16) 0.72598(14) 0.0336(3) Uani 1 1 d . . . H14 H 0.5587 0.4990 0.7944 0.040 Uiso 1 1 calc R . . C15 C 0.47823(6) 0.54153(16) 0.67485(13) 0.0293(3) Uani 1 1 d . . . H15 H 0.4564 0.4645 0.7093 0.035 Uiso 1 1 calc R . . C16 C 0.25883(6) 0.57125(15) 0.98532(12) 0.0255(3) Uani 1 1 d . . . C17 C 0.25627(6) 0.51252(18) 1.10641(13) 0.0326(3) Uani 1 1 d . . . H17 H 0.2891 0.4559 1.1528 0.039 Uiso 1 1 calc R . . C18 C 0.20615(7) 0.53632(18) 1.15932(14) 0.0375(4) Uani 1 1 d . . . H18 H 0.2033 0.4935 1.2404 0.045 Uiso 1 1 calc R . . C19 C 0.16045(7) 0.62380(18) 1.09136(15) 0.0368(3) Uani 1 1 d . . . C20 C 0.16181(7) 0.68789(18) 0.97422(15) 0.0376(4) Uani 1 1 d . . . H20 H 0.1298 0.7499 0.9313 0.045 Uiso 1 1 calc R . . C21 C 0.21165(6) 0.65916(16) 0.92029(13) 0.0308(3) Uani 1 1 d . . . H21 H 0.2135 0.7000 0.8380 0.037 Uiso 1 1 calc R . . C22 C 0.13280(6) 0.35143(16) 0.55059(13) 0.0301(3) Uani 1 1 d . . . C23 C 0.11693(6) 0.46790(18) 0.62656(14) 0.0348(3) Uani 1 1 d . . . H23 H 0.1443 0.5490 0.6536 0.042 Uiso 1 1 calc R . . C24 C 0.06171(7) 0.4680(2) 0.66369(16) 0.0454(4) Uani 1 1 d . . . H24 H 0.0507 0.5481 0.7153 0.055 Uiso 1 1 calc R . . C25 C 0.02373(7) 0.3491(2) 0.62349(19) 0.0540(5) Uani 1 1 d . . . C26 C 0.03674(8) 0.2340(2) 0.5459(2) 0.0605(5) Uani 1 1 d . . . H26 H 0.0087 0.1544 0.5184 0.073 Uiso 1 1 calc R . . C27 C 0.09144(7) 0.23562(19) 0.50839(17) 0.0444(4) Uani 1 1 d . . . H27 H 0.1010 0.1574 0.4534 0.053 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 O1 0.0318(5) 0.0431(6) 0.0254(5) 0.0064(4) 0.0049(4) -0.0036(4) O2 0.0240(5) 0.0508(6) 0.0283(5) 0.0007(4) 0.0026(4) 0.0037(4) O3 0.0422(6) 0.0522(7) 0.0330(6) -0.0134(5) 0.0090(5) -0.0094(5) F1 0.0270(4) 0.0479(5) 0.0701(7) 0.0003(5) -0.0080(4) -0.0046(4) F2 0.0394(5) 0.0765(7) 0.0635(7) -0.0049(5) 0.0302(5) 0.0089(5) F3 0.0331(6) 0.1314(12) 0.1089(11) -0.0141(9) 0.0313(6) -0.0199(6) C1 0.0272(7) 0.0312(7) 0.0218(6) -0.0008(5) 0.0066(5) 0.0008(5) C2 0.0235(6) 0.0268(7) 0.0259(7) 0.0006(5) 0.0068(5) 0.0023(5) C3 0.0228(6) 0.0293(7) 0.0258(7) -0.0029(5) 0.0048(5) -0.0001(5) C4 0.0228(6) 0.0283(7) 0.0233(6) 0.0003(5) 0.0062(5) 0.0035(5) C5 0.0236(6) 0.0290(7) 0.0262(7) 0.0017(5) 0.0082(5) 0.0014(5) C6 0.0242(6) 0.0265(7) 0.0256(7) -0.0002(5) 0.0048(5) -0.0005(5) C7 0.0266(7) 0.0253(6) 0.0261(7) -0.0009(5) 0.0080(5) 0.0005(5) C8 0.0251(7) 0.0284(7) 0.0243(7) 0.0011(5) 0.0048(5) -0.0001(5) C9 0.0303(7) 0.0294(7) 0.0260(7) 0.0000(5) 0.0038(6) -0.0023(5) C10 0.0248(6) 0.0286(7) 0.0245(6) -0.0028(5) 0.0085(5) 0.0009(5) C11 0.0290(7) 0.0328(7) 0.0299(7) 0.0034(6) 0.0057(6) -0.0004(6) C12 0.0316(7) 0.0317(7) 0.0407(8) 0.0006(6) 0.0097(6) -0.0048(6) C13 0.0236(7) 0.0338(7) 0.0388(8) -0.0090(6) 0.0012(6) -0.0005(6) C14 0.0325(7) 0.0360(8) 0.0310(7) 0.0005(6) 0.0029(6) 0.0058(6) C15 0.0300(7) 0.0319(7) 0.0278(7) 0.0024(6) 0.0098(6) 0.0012(6) C16 0.0251(6) 0.0298(7) 0.0216(6) -0.0033(5) 0.0041(5) -0.0003(5) C17 0.0303(7) 0.0422(8) 0.0248(7) 0.0016(6) 0.0045(6) 0.0043(6) C18 0.0389(8) 0.0498(9) 0.0264(7) 0.0003(6) 0.0129(6) 0.0000(7) C19 0.0286(7) 0.0463(9) 0.0393(8) -0.0100(7) 0.0160(6) 0.0005(6) C20 0.0316(8) 0.0431(9) 0.0372(8) -0.0028(7) 0.0040(6) 0.0106(6) C21 0.0314(7) 0.0356(7) 0.0257(7) 0.0000(6) 0.0062(6) 0.0055(6) C22 0.0261(7) 0.0334(7) 0.0293(7) 0.0024(6) 0.0017(6) -0.0037(5) C23 0.0273(7) 0.0415(8) 0.0346(8) -0.0005(6) 0.0038(6) -0.0028(6) C24 0.0305(8) 0.0624(11) 0.0436(9) -0.0036(8) 0.0079(7) 0.0024(7) C25 0.0242(8) 0.0782(13) 0.0611(11) 0.0019(10) 0.0122(7) -0.0087(8) C26 0.0341(9) 0.0629(12) 0.0829(14) -0.0071(11) 0.0072(9) -0.0222(8) C27 0.0340(8) 0.0437(9) 0.0530(10) -0.0083(7) 0.0020(7) -0.0101(7) _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 O1 C7 1.2194(16) . ? O2 C8 1.2176(15) . ? O3 C9 1.2200(17) . ? F1 C13 1.3582(15) . ? F2 C19 1.3652(17) . ? F3 C25 1.3597(19) . ? C1 C6 1.3894(18) . ? C1 C2 1.3962(18) . ? C1 H1 0.9500 . ? C2 C3 1.3970(18) . ? C2 C7 1.4985(18) . ? C3 C4 1.3921(18) . ? C3 H3 0.9500 . ? C4 C5 1.3920(18) . ? C4 C8 1.4999(18) . ? C5 C6 1.3995(18) . ? C5 H5 0.9500 . ? C6 C9 1.5011(18) . ? C7 C10 1.4937(18) . ? C8 C16 1.4914(18) . ? C9 C22 1.4952(19) . ? C10 C15 1.3947(19) . ? C10 C11 1.3953(19) . ? C11 C12 1.3806(19) . ? C11 H11 0.9500 . ? C12 C13 1.374(2) . ? C12 H12 0.9500 . ? C13 C14 1.375(2) . ? C14 C15 1.3887(19) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.3891(19) . ? C16 C17 1.3931(19) . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 C19 1.376(2) . ? C18 H18 0.9500 . ? C19 C20 1.367(2) . ? C20 C21 1.388(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.387(2) . ? C22 C27 1.394(2) . ? C23 C24 1.388(2) . ? C23 H23 0.9500 . ? C24 C25 1.365(3) . ? C24 H24 0.9500 . ? C25 C26 1.366(3) . ? C26 C27 1.378(2) . ? C26 H26 0.9500 . ? C27 H27 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 C6 C1 C2 121.11(12) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C1 C2 C3 119.18(12) . . ? C1 C2 C7 117.88(11) . . ? C3 C2 C7 122.78(11) . . ? C4 C3 C2 120.26(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.94(12) . . ? C5 C4 C8 120.76(12) . . ? C3 C4 C8 119.26(11) . . ? C4 C5 C6 120.42(12) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.06(12) . . ? C1 C6 C9 118.31(12) . . ? C5 C6 C9 122.63(12) . . ? O1 C7 C10 120.67(12) . . ? O1 C7 C2 119.02(11) . . ? C10 C7 C2 120.31(11) . . ? O2 C8 C16 121.11(12) . . ? O2 C8 C4 120.76(12) . . ? C16 C8 C4 118.12(11) . . ? O3 C9 C22 119.91(12) . . ? O3 C9 C6 119.80(13) . . ? C22 C9 C6 120.28(12) . . ? C15 C10 C11 118.92(12) . . ? C15 C10 C7 122.73(12) . . ? C11 C10 C7 118.24(12) . . ? C12 C11 C10 120.69(13) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 118.34(13) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? F1 C13 C12 118.18(13) . . ? F1 C13 C14 118.43(13) . . ? C12 C13 C14 123.38(13) . . ? C13 C14 C15 117.57(13) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C14 C15 C10 121.08(13) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C21 C16 C17 119.58(13) . . ? C21 C16 C8 121.11(12) . . ? C17 C16 C8 119.31(12) . . ? C18 C17 C16 120.25(13) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 118.12(14) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? F2 C19 C20 118.43(14) . . ? F2 C19 C18 117.91(14) . . ? C20 C19 C18 123.67(14) . . ? C19 C20 C21 117.62(13) . . ? C19 C20 H20 121.2 . . ? C21 C20 H20 121.2 . . ? C20 C21 C16 120.70(13) . . ? C20 C21 H21 119.7 . . ? C16 C21 H21 119.7 . . ? C23 C22 C27 118.81(14) . . ? C23 C22 C9 123.05(12) . . ? C27 C22 C9 118.06(13) . . ? C22 C23 C24 121.13(14) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C25 C24 C23 117.66(16) . . ? C25 C24 H24 121.2 . . ? C23 C24 H24 121.2 . . ? F3 C25 C24 117.95(18) . . ? F3 C25 C26 118.74(16) . . ? C24 C25 C26 123.30(16) . . ? C25 C26 C27 118.61(16) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C26 C27 C22 120.42(16) . . ? C26 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.195 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.051 #====END # End of Crystallographic Information File