Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. #TrackingRef '- 12-Core final.cif' _journal_coden_Cambridge 0182 _audit_update_record ; 2008-09-06 # Formatted by publCIF ; #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Rhett C. Smith' _publ_contact_author_address ; Department of Chemistry and COMSET Clemson University Clemson, SC 29634-0973 USA ; _publ_contact_author_email rhett@Clemson.edu _publ_contact_author_fax 864-656-6613 _publ_contact_author_phone 864-656-6112 _publ_contact_letter ? _publ_requested_category ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Title (type here to add) ; _publ_section_title_footnote ; ? # ENTER any Title footnote here if needed. ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Jessica Hanley' . . 'Kristine Jecen' . . 'Charles McGill' . . 'Grant Robertson' . . B.P.Morgan . ; Department of Chemistry and COMSET Clemson University Clemson, SC 29634-0973 USA ; A.Mangalum . ; Department of Chemistry and COMSET Clemson University Clemson, SC 29634-0973 USA ; ; R.C.Smith ; . ; Department of Chemistry and COMSET Clemson University Clemson, SC 29634-0973 USA ; #====================================================================== # 4. TEXT _publ_section_abstract ; (type here to add abstract) ; _publ_section_comment ; (type here to add) ; _publ_section_exptl_prep ; (type here to add preparation details) ; _publ_section_exptl_refinement ; (type here to add refinement details) ; _publ_section_references ; ? ; _publ_section_figure_captions ; ; _publ_section_table_legends ? _publ_section_acknowledgements ? data_am-1-2-i-br-oxycylcophane _database_code_depnum_ccdc_archive 'CCDC 768761' #TrackingRef '- 12-Core final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 Br I3 O2' _chemical_formula_sum 'C26 H16 Br I3 O2' _chemical_formula_weight 821.00 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' 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 'P 1 21/n 1' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6033(15) _cell_length_b 19.178(4) _cell_length_c 18.272(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.12(3) _cell_angle_gamma 90.00 _cell_volume 2622.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7749 _cell_measurement_theta_min 2.4073 _cell_measurement_theta_max 26.3590 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.079 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 5.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1896 _exptl_absorpt_correction_T_max 0.5440 _exptl_absorpt_process_details 'REQAB, Rigaku/MSC, The Woodlands, TX, USA, 1999.' _exptl_special_details ? _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_measurement_method omega _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 260 Slice: -40.0000 - 90.0000 Image width: 0.5000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 27.6735 2theta: -0.1699 scan: Number of images: 260 Slice: -40.0000 - 90.0000 Image width: 0.5000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 27.6735 2theta: -0.1699 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3 circle ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4651 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4651 _reflns_number_gt 4120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC,2001)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC,2001)' _computing_data_reduction 'CrystalClear (Rigaku/MSC,2001)' _computing_structure_solution 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_structure_refinement 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_molecular_graphics 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_publication_material 'SHELXTL 6.10 (Bruker AXS,2000)' _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^)+(0.0431P)^2^+10.0879P] 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 4651 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 0.85988(5) 0.29247(2) 0.862327(19) 0.02538(11) Uani 1 1 d . . . I2 I 0.20464(6) 0.13251(2) 1.03011(2) 0.03332(13) Uani 1 1 d . . . I3 I 0.54600(6) -0.06013(2) 0.76384(2) 0.03030(12) Uani 1 1 d . . . Br1 Br 0.24655(8) 0.27419(3) 0.55083(3) 0.02578(14) Uani 1 1 d . . . O1 O 0.4590(5) 0.1792(2) 0.9138(2) 0.0224(8) Uani 1 1 d . . . O2 O 0.5781(5) 0.1023(2) 0.8032(2) 0.0224(8) Uani 1 1 d . . . C1 C 0.6533(7) 0.2704(3) 0.7730(3) 0.0187(11) Uani 1 1 d . . . C2 C 0.6838(7) 0.2261(3) 0.7154(3) 0.0185(11) Uani 1 1 d . . . C3 C 0.5597(7) 0.2272(3) 0.6486(3) 0.0201(11) Uani 1 1 d . . . H3 H 0.5796 0.1996 0.6077 0.024 Uiso 1 1 calc R . . C4 C 0.4076(7) 0.2688(3) 0.6422(3) 0.0214(11) Uani 1 1 d . . . C5 C 0.3702(8) 0.3062(3) 0.7031(3) 0.0240(12) Uani 1 1 d . . . H5 H 0.2606 0.3308 0.6994 0.029 Uiso 1 1 calc R . . C6 C 0.4924(7) 0.3074(3) 0.7692(3) 0.0198(11) Uani 1 1 d . . . C7 C 0.4434(7) 0.3395(3) 0.8367(3) 0.0203(11) Uani 1 1 d . . . C8 C 0.4712(8) 0.4093(3) 0.8519(3) 0.0261(12) Uani 1 1 d . . . H8 H 0.5189 0.4383 0.8180 0.031 Uiso 1 1 calc R . . C9 C 0.4296(9) 0.4377(3) 0.9172(3) 0.0301(13) Uani 1 1 d . . . H9 H 0.4488 0.4859 0.9274 0.036 Uiso 1 1 calc R . . C10 C 0.3606(8) 0.3961(3) 0.9671(3) 0.0300(13) Uani 1 1 d . . . H10 H 0.3371 0.4151 1.0125 0.036 Uiso 1 1 calc R . . C11 C 0.3264(8) 0.3267(3) 0.9503(3) 0.0254(12) Uani 1 1 d . . . H11 H 0.2749 0.2983 0.9836 0.030 Uiso 1 1 calc R . . C12 C 0.3660(7) 0.2977(3) 0.8854(3) 0.0221(12) Uani 1 1 d . . . C13 C 0.3246(7) 0.2224(3) 0.8686(3) 0.0224(11) Uani 1 1 d . . . H13A H 0.2049 0.2110 0.8795 0.027 Uiso 1 1 calc R . . H13B H 0.3240 0.2132 0.8152 0.027 Uiso 1 1 calc R . . C14 C 0.4192(7) 0.1087(3) 0.9065(3) 0.0183(11) Uani 1 1 d . . . C15 C 0.3176(7) 0.0756(3) 0.9521(3) 0.0246(12) Uani 1 1 d . . . C16 C 0.2836(8) 0.0047(3) 0.9463(3) 0.0270(12) Uani 1 1 d . . . H16 H 0.2134 -0.0174 0.9778 0.032 Uiso 1 1 calc R . . C17 C 0.3536(8) -0.0337(3) 0.8938(3) 0.0276(13) Uani 1 1 d . . . H17 H 0.3337 -0.0825 0.8902 0.033 Uiso 1 1 calc R . . C18 C 0.4533(8) -0.0010(3) 0.8460(3) 0.0241(12) Uani 1 1 d . . . C19 C 0.4872(7) 0.0700(3) 0.8510(3) 0.0205(11) Uani 1 1 d . . . C20 C 0.7672(8) 0.1092(3) 0.8327(3) 0.0239(12) Uani 1 1 d . . . H20A H 0.8108 0.0659 0.8594 0.029 Uiso 1 1 calc R . . H20B H 0.7857 0.1482 0.8687 0.029 Uiso 1 1 calc R . . C21 C 0.8739(7) 0.1226(3) 0.7716(3) 0.0213(11) Uani 1 1 d . . . C22 C 1.0143(8) 0.0774(3) 0.7661(3) 0.0247(12) Uani 1 1 d . . . H22 H 1.0377 0.0398 0.8003 0.030 Uiso 1 1 calc R . . C23 C 1.1214(7) 0.0855(3) 0.7123(3) 0.0244(12) Uani 1 1 d . . . H23 H 1.2162 0.0538 0.7099 0.029 Uiso 1 1 calc R . . C24 C 1.0888(8) 0.1397(3) 0.6627(3) 0.0301(13) Uani 1 1 d . . . H24 H 1.1623 0.1460 0.6262 0.036 Uiso 1 1 calc R . . C25 C 0.9499(8) 0.1847(3) 0.6659(3) 0.0249(12) Uani 1 1 d . . . H25 H 0.9285 0.2219 0.6310 0.030 Uiso 1 1 calc R . . C26 C 0.8385(7) 0.1774(3) 0.7191(3) 0.0205(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0224(2) 0.0286(2) 0.02313(19) -0.00119(14) -0.00142(14) 0.00140(14) I2 0.0407(3) 0.0329(2) 0.0307(2) 0.00081(16) 0.01827(17) 0.00691(18) I3 0.0374(2) 0.0256(2) 0.0295(2) -0.00628(15) 0.01017(17) 0.00204(16) Br1 0.0253(3) 0.0322(3) 0.0183(3) 0.0014(2) -0.0003(2) 0.0004(2) O1 0.021(2) 0.019(2) 0.0263(19) -0.0032(15) 0.0024(15) 0.0009(16) O2 0.0182(19) 0.023(2) 0.0267(19) 0.0043(15) 0.0055(15) -0.0006(15) C1 0.018(3) 0.018(3) 0.020(2) 0.002(2) 0.002(2) -0.003(2) C2 0.019(3) 0.018(3) 0.018(2) 0.001(2) 0.005(2) -0.001(2) C3 0.028(3) 0.016(3) 0.017(2) 0.002(2) 0.007(2) 0.001(2) C4 0.022(3) 0.022(3) 0.019(2) 0.002(2) 0.001(2) -0.003(2) C5 0.019(3) 0.026(3) 0.027(3) -0.002(2) 0.002(2) 0.004(2) C6 0.023(3) 0.019(3) 0.017(2) 0.000(2) 0.002(2) 0.003(2) C7 0.017(3) 0.017(3) 0.026(3) 0.001(2) 0.002(2) 0.005(2) C8 0.027(3) 0.019(3) 0.033(3) -0.005(2) 0.005(2) 0.000(2) C9 0.035(3) 0.016(3) 0.036(3) -0.005(2) 0.000(3) 0.002(2) C10 0.032(3) 0.029(3) 0.029(3) -0.012(2) 0.006(2) 0.010(3) C11 0.029(3) 0.024(3) 0.021(3) 0.002(2) -0.001(2) 0.002(2) C12 0.022(3) 0.020(3) 0.023(3) 0.000(2) 0.000(2) 0.007(2) C13 0.018(3) 0.022(3) 0.026(3) -0.002(2) 0.001(2) -0.001(2) C14 0.013(3) 0.015(3) 0.025(3) 0.001(2) -0.002(2) 0.003(2) C15 0.017(3) 0.031(3) 0.027(3) -0.004(2) 0.006(2) 0.005(2) C16 0.026(3) 0.029(3) 0.027(3) 0.003(2) 0.006(2) -0.001(2) C17 0.031(3) 0.015(3) 0.036(3) 0.008(2) 0.004(3) -0.005(2) C18 0.024(3) 0.024(3) 0.023(3) -0.001(2) 0.002(2) -0.003(2) C19 0.022(3) 0.024(3) 0.015(2) 0.000(2) 0.001(2) 0.001(2) C20 0.027(3) 0.020(3) 0.025(3) 0.007(2) 0.008(2) 0.000(2) C21 0.018(3) 0.026(3) 0.020(3) 0.005(2) 0.002(2) -0.003(2) C22 0.027(3) 0.018(3) 0.029(3) -0.002(2) 0.004(2) -0.002(2) C23 0.018(3) 0.028(3) 0.026(3) -0.004(2) 0.003(2) 0.003(2) C24 0.029(3) 0.036(3) 0.029(3) -0.007(3) 0.013(2) -0.004(3) C25 0.024(3) 0.022(3) 0.030(3) 0.002(2) 0.007(2) 0.000(2) C26 0.019(3) 0.019(3) 0.022(3) 0.003(2) -0.001(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.100(5) . ? I2 C15 2.095(5) . ? I3 C18 2.100(6) . ? Br1 C4 1.892(5) . ? O1 C14 1.385(6) . ? O1 C13 1.455(6) . ? O2 C19 1.355(7) . ? O2 C20 1.451(7) . ? C1 C2 1.403(7) . ? C1 C6 1.405(8) . ? C2 C3 1.406(7) . ? C2 C26 1.494(8) . ? C3 C4 1.393(8) . ? C3 H3 0.9500 . ? C4 C5 1.394(8) . ? C5 C6 1.388(8) . ? C5 H5 0.9500 . ? C6 C7 1.484(7) . ? C7 C8 1.376(8) . ? C7 C12 1.402(8) . ? C8 C9 1.397(8) . ? C8 H8 0.9500 . ? C9 C10 1.383(9) . ? C9 H9 0.9500 . ? C10 C11 1.381(8) . ? C10 H10 0.9500 . ? C11 C12 1.390(8) . ? C11 H11 0.9500 . ? C12 C13 1.499(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.386(8) . ? C14 C19 1.426(7) . ? C15 C16 1.385(9) . ? C16 C17 1.387(9) . ? C16 H16 0.9500 . ? C17 C18 1.401(8) . ? C17 H17 0.9500 . ? C18 C19 1.386(8) . ? C20 C21 1.512(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.392(8) . ? C21 C26 1.416(7) . ? C22 C23 1.392(8) . ? C22 H22 0.9500 . ? C23 C24 1.371(9) . ? C23 H23 0.9500 . ? C24 C25 1.374(8) . ? C24 H24 0.9500 . ? C25 C26 1.405(8) . ? C25 H25 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 C14 O1 C13 112.4(4) . . ? C19 O2 C20 112.8(4) . . ? C2 C1 C6 121.7(5) . . ? C2 C1 I1 120.3(4) . . ? C6 C1 I1 117.6(4) . . ? C1 C2 C3 117.9(5) . . ? C1 C2 C26 125.2(5) . . ? C3 C2 C26 116.8(5) . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 Br1 120.2(4) . . ? C5 C4 Br1 119.1(4) . . ? C6 C5 C4 120.2(5) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 118.6(5) . . ? C5 C6 C7 120.2(5) . . ? C1 C6 C7 120.8(5) . . ? C8 C7 C12 119.6(5) . . ? C8 C7 C6 121.4(5) . . ? C12 C7 C6 119.0(5) . . ? C7 C8 C9 120.1(6) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.5(5) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 121.0(6) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 119.4(5) . . ? C11 C12 C13 119.4(5) . . ? C7 C12 C13 121.2(5) . . ? O1 C13 C12 109.4(4) . . ? O1 C13 H13A 109.8 . . ? C12 C13 H13A 109.8 . . ? O1 C13 H13B 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O1 C14 C15 121.7(5) . . ? O1 C14 C19 118.4(5) . . ? C15 C14 C19 119.9(5) . . ? C16 C15 C14 121.4(5) . . ? C16 C15 I2 118.1(4) . . ? C14 C15 I2 120.5(4) . . ? C15 C16 C17 119.0(5) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C18 120.6(5) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 120.9(5) . . ? C19 C18 I3 119.7(4) . . ? C17 C18 I3 119.4(4) . . ? O2 C19 C18 121.1(5) . . ? O2 C19 C14 120.7(5) . . ? C18 C19 C14 118.2(5) . . ? O2 C20 C21 111.5(4) . . ? O2 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? O2 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C26 118.1(5) . . ? C22 C21 C20 117.7(5) . . ? C26 C21 C20 124.3(5) . . ? C21 C22 C23 122.2(5) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C24 C23 C22 119.4(5) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.0(6) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 121.8(5) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C25 C26 C21 118.5(5) . . ? C25 C26 C2 118.1(5) . . ? C21 C26 C2 123.3(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.997 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.153 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 138 40 ' ' 2 0.500 1.000 0.500 138 40 ' ' _platon_squeeze_details ; ; # Attachment '14-Core--pub.cif.txt' data_am-1-4-i-br-oxycylcophane _database_code_depnum_ccdc_archive 'CCDC 768762' #TrackingRef '14-Core--pub.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 Br I3 O2' _chemical_formula_sum 'C26 H16 Br I3 O2' _chemical_formula_weight 821.00 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' 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 'P 1 21/c 1' _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 10.633(2) _cell_length_b 14.065(3) _cell_length_c 32.946(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.61(3) _cell_angle_gamma 90.00 _cell_volume 4911.3(17) _cell_formula_units_Z 8 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 13125 _cell_measurement_theta_min 2.4460 _cell_measurement_theta_max 26.3732 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3056 _exptl_absorpt_coefficient_mu 5.467 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2063 _exptl_absorpt_correction_T_max 0.6798 _exptl_absorpt_process_details 'REQAB, Rigaku/MSC, The Woodlands, TX, USA, 1999.' _exptl_special_details ? _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_measurement_method omega _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 280 Slice: -50.0000 - 90.0000 Image width: 0.5000 Exp time: 15.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 37.7606 2theta: 8.4652 scan: Number of images: 280 Slice: -50.0000 - 90.0000 Image width: 0.5000 Exp time: 15.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 37.7606 2theta: 8.4652 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3 circle ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34118 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.36 _reflns_number_total 9932 _reflns_number_gt 8573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC,2001)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC,2001)' _computing_data_reduction 'CrystalClear (Rigaku/MSC,2001)' _computing_structure_solution 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_structure_refinement 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_molecular_graphics 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_publication_material 'SHELXTL 6.10 (Bruker AXS,2000)' _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^)+(0.0354P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9932 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.002 _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 0.48591(3) 0.77004(2) 0.517548(10) 0.02860(8) Uani 1 1 d . . . I2 I 0.29382(3) 0.97809(2) 0.457658(10) 0.03160(9) Uani 1 1 d . . . I3 I 0.70596(3) 0.77778(2) 0.329366(10) 0.03274(9) Uani 1 1 d . . . I4 I 0.58414(2) 0.10047(2) 0.231795(9) 0.02405(8) Uani 1 1 d . . . I5 I 0.63287(3) 0.37969(2) 0.251808(11) 0.03375(9) Uani 1 1 d . . . I6 I 1.22339(3) 0.17155(2) 0.276472(10) 0.03004(8) Uani 1 1 d . . . Br1 Br 0.67733(5) 0.48891(3) 0.368168(17) 0.03493(13) Uani 1 1 d . . . Br2 Br 1.08858(4) -0.06664(3) 0.348689(15) 0.02834(11) Uani 1 1 d . . . O1 O 0.7630(3) 0.9147(2) 0.41249(10) 0.0260(7) Uani 1 1 d . . . O2 O 0.2605(3) 0.8051(2) 0.39649(10) 0.0269(7) Uani 1 1 d . . . O3 O 1.0157(3) 0.1776(2) 0.19556(9) 0.0232(7) Uani 1 1 d . . . O4 O 0.7996(3) 0.3176(2) 0.33070(10) 0.0261(7) Uani 1 1 d . . . C1 C 0.5482(4) 0.6853(3) 0.47066(14) 0.0209(9) Uani 1 1 d . . . C2 C 0.4585(4) 0.6270(3) 0.44854(14) 0.0202(9) Uani 1 1 d . . . C3 C 0.4984(4) 0.5697(3) 0.41762(15) 0.0240(10) Uani 1 1 d . . . H3 H 0.4395 0.5300 0.4025 0.029 Uiso 1 1 calc R . . C4 C 0.6237(4) 0.5704(3) 0.40886(14) 0.0234(10) Uani 1 1 d . . . C5 C 0.7114(4) 0.6272(3) 0.43099(15) 0.0244(10) Uani 1 1 d . . . H5 H 0.7973 0.6254 0.4250 0.029 Uiso 1 1 calc R . . C6 C 0.6756(4) 0.6865(3) 0.46173(14) 0.0212(9) Uani 1 1 d . . . C7 C 0.7741(4) 0.7430(3) 0.48652(15) 0.0244(10) Uani 1 1 d . . . C8 C 0.7945(4) 0.7222(4) 0.52778(16) 0.0316(11) Uani 1 1 d . . . H8 H 0.7450 0.6741 0.5390 0.038 Uiso 1 1 calc R . . C9 C 0.8847(5) 0.7692(4) 0.55327(18) 0.0391(13) Uani 1 1 d . . . H9 H 0.8963 0.7533 0.5814 0.047 Uiso 1 1 calc R . . C10 C 0.9577(5) 0.8397(4) 0.53713(18) 0.0396(13) Uani 1 1 d . . . H10 H 1.0192 0.8730 0.5541 0.047 Uiso 1 1 calc R . . C11 C 0.9397(4) 0.8610(4) 0.49603(17) 0.0340(12) Uani 1 1 d . . . H11 H 0.9899 0.9092 0.4852 0.041 Uiso 1 1 calc R . . C12 C 0.8500(4) 0.8137(3) 0.46998(14) 0.0240(10) Uani 1 1 d . . . C13 C 0.8480(4) 0.8373(3) 0.42564(15) 0.0270(10) Uani 1 1 d . . . H13A H 0.9345 0.8544 0.4193 0.032 Uiso 1 1 calc R . . H13B H 0.8230 0.7797 0.4097 0.032 Uiso 1 1 calc R . . C14 C 0.6385(4) 0.8878(3) 0.40599(14) 0.0213(9) Uani 1 1 d . . . C15 C 0.5517(4) 0.9301(3) 0.42987(15) 0.0246(10) Uani 1 1 d . . . H15 H 0.5795 0.9765 0.4495 0.029 Uiso 1 1 calc R . . C16 C 0.4248(4) 0.9051(3) 0.42527(15) 0.0239(10) Uani 1 1 d . . . C17 C 0.3848(4) 0.8335(3) 0.39804(14) 0.0208(9) Uani 1 1 d . . . C18 C 0.4683(4) 0.7985(3) 0.37159(15) 0.0258(10) Uani 1 1 d . . . H18 H 0.4390 0.7547 0.3510 0.031 Uiso 1 1 calc R . . C19 C 0.5940(4) 0.8261(3) 0.37445(14) 0.0242(10) Uani 1 1 d . . . C20 C 0.2363(4) 0.7040(3) 0.39278(14) 0.0243(10) Uani 1 1 d . . . H20A H 0.3067 0.6731 0.3799 0.029 Uiso 1 1 calc R . . H20B H 0.1581 0.6935 0.3750 0.029 Uiso 1 1 calc R . . C21 C 0.2227(4) 0.6591(3) 0.43375(15) 0.0224(10) Uani 1 1 d . . . C22 C 0.1027(4) 0.6546(3) 0.44760(16) 0.0286(11) Uani 1 1 d . . . H22 H 0.0342 0.6819 0.4313 0.034 Uiso 1 1 calc R . . C23 C 0.0790(4) 0.6123(4) 0.48375(17) 0.0359(12) Uani 1 1 d . . . H23 H -0.0041 0.6110 0.4924 0.043 Uiso 1 1 calc R . . C24 C 0.1788(4) 0.5715(4) 0.50737(18) 0.0364(12) Uani 1 1 d . . . H24 H 0.1640 0.5404 0.5321 0.044 Uiso 1 1 calc R . . C25 C 0.2995(4) 0.5760(4) 0.49492(16) 0.0326(11) Uani 1 1 d . . . H25 H 0.3669 0.5474 0.5113 0.039 Uiso 1 1 calc R . . C26 C 0.3246(4) 0.6212(3) 0.45913(15) 0.0244(10) Uani 1 1 d . . . C27 C 0.7442(4) 0.0487(3) 0.26758(14) 0.0207(9) Uani 1 1 d . . . C28 C 0.7515(4) 0.0632(3) 0.30995(14) 0.0191(9) Uani 1 1 d . . . C29 C 0.8569(4) 0.0288(3) 0.33294(14) 0.0221(9) Uani 1 1 d . . . H29 H 0.8641 0.0381 0.3616 0.027 Uiso 1 1 calc R . . C30 C 0.9503(4) -0.0182(3) 0.31510(15) 0.0227(10) Uani 1 1 d . . . C31 C 0.9428(4) -0.0337(3) 0.27351(14) 0.0213(9) Uani 1 1 d . . . H31 H 1.0074 -0.0682 0.2616 0.026 Uiso 1 1 calc R . . C32 C 0.8395(4) 0.0015(3) 0.24897(14) 0.0197(9) Uani 1 1 d . . . C33 C 0.8367(4) -0.0169(3) 0.20394(14) 0.0204(9) Uani 1 1 d . . . C34 C 0.7399(4) -0.0745(3) 0.18570(16) 0.0282(11) Uani 1 1 d . . . H34 H 0.6783 -0.1002 0.2020 0.034 Uiso 1 1 calc R . . C35 C 0.7328(5) -0.0945(3) 0.14444(17) 0.0369(13) Uani 1 1 d . . . H35 H 0.6660 -0.1326 0.1325 0.044 Uiso 1 1 calc R . . C36 C 0.8228(5) -0.0589(4) 0.12071(17) 0.0369(13) Uani 1 1 d . . . H36 H 0.8170 -0.0716 0.0923 0.044 Uiso 1 1 calc R . . C37 C 0.9219(5) -0.0046(3) 0.13819(15) 0.0311(11) Uani 1 1 d . . . H37 H 0.9853 0.0177 0.1218 0.037 Uiso 1 1 calc R . . C38 C 0.9292(4) 0.0176(3) 0.17988(14) 0.0238(10) Uani 1 1 d . . . C39 C 1.0414(4) 0.0758(3) 0.19611(15) 0.0238(10) Uani 1 1 d . . . H39A H 1.0667 0.0558 0.2244 0.029 Uiso 1 1 calc R . . H39B H 1.1131 0.0628 0.1795 0.029 Uiso 1 1 calc R . . C40 C 0.9680(4) 0.2145(3) 0.22989(14) 0.0202(9) Uani 1 1 d . . . C41 C 0.8510(4) 0.2599(3) 0.22539(15) 0.0235(10) Uani 1 1 d . . . H41 H 0.8072 0.2644 0.1992 0.028 Uiso 1 1 calc R . . C42 C 0.7982(4) 0.2984(3) 0.25880(14) 0.0208(9) Uani 1 1 d . . . C43 C 0.8583(4) 0.2868(3) 0.29769(14) 0.0206(9) Uani 1 1 d . . . C44 C 0.9782(4) 0.2492(3) 0.30116(14) 0.0219(9) Uani 1 1 d . . . H44 H 1.0234 0.2470 0.3272 0.026 Uiso 1 1 calc R . . C45 C 1.0338(4) 0.2151(3) 0.26825(14) 0.0198(9) Uani 1 1 d . . . C46 C 0.7849(4) 0.2458(3) 0.36179(14) 0.0230(9) Uani 1 1 d . . . H46A H 0.7875 0.2773 0.3887 0.028 Uiso 1 1 calc R . . H46B H 0.8571 0.2013 0.3623 0.028 Uiso 1 1 calc R . . C47 C 0.6631(4) 0.1894(3) 0.35524(14) 0.0211(9) Uani 1 1 d . . . C48 C 0.5606(4) 0.2206(3) 0.37614(15) 0.0259(10) Uani 1 1 d . . . H48 H 0.5684 0.2779 0.3914 0.031 Uiso 1 1 calc R . . C49 C 0.4485(4) 0.1701(3) 0.37514(15) 0.0288(11) Uani 1 1 d . . . H49 H 0.3802 0.1932 0.3892 0.035 Uiso 1 1 calc R . . C50 C 0.4370(4) 0.0859(3) 0.35343(16) 0.0290(11) Uani 1 1 d . . . H50 H 0.3618 0.0493 0.3534 0.035 Uiso 1 1 calc R . . C51 C 0.5349(4) 0.0553(3) 0.33187(15) 0.0267(10) Uani 1 1 d . . . H51 H 0.5255 -0.0016 0.3164 0.032 Uiso 1 1 calc R . . C52 C 0.6481(4) 0.1062(3) 0.33222(14) 0.0210(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03156(16) 0.03101(17) 0.02383(17) -0.00304(13) 0.00608(13) 0.00163(13) I2 0.02904(16) 0.03327(18) 0.03286(19) -0.00687(14) 0.00485(14) 0.00601(13) I3 0.04087(18) 0.02921(17) 0.03019(19) -0.00286(13) 0.01556(14) -0.00099(14) I4 0.02101(14) 0.02355(15) 0.02683(18) 0.00316(12) -0.00271(12) 0.00031(11) I5 0.02906(16) 0.02930(17) 0.0425(2) 0.00114(14) 0.00038(14) 0.01150(13) I6 0.02125(14) 0.03274(17) 0.0356(2) -0.00266(14) -0.00109(13) 0.00416(12) Br1 0.0399(3) 0.0253(3) 0.0419(3) -0.0089(2) 0.0178(2) -0.0014(2) Br2 0.0256(2) 0.0324(3) 0.0262(3) 0.0037(2) -0.00264(19) 0.00830(19) O1 0.0247(15) 0.0246(16) 0.0289(19) 0.0051(14) 0.0029(14) 0.0009(13) O2 0.0223(15) 0.0199(16) 0.038(2) 0.0013(14) -0.0025(14) 0.0018(13) O3 0.0309(16) 0.0176(15) 0.0220(17) 0.0004(13) 0.0076(13) 0.0011(13) O4 0.0321(16) 0.0203(16) 0.0273(19) -0.0008(13) 0.0117(14) 0.0032(13) C1 0.027(2) 0.018(2) 0.018(2) 0.0050(17) 0.0049(18) 0.0069(18) C2 0.020(2) 0.018(2) 0.022(2) 0.0037(18) -0.0023(18) 0.0033(17) C3 0.024(2) 0.023(2) 0.026(3) 0.0024(19) 0.0044(19) -0.0004(18) C4 0.030(2) 0.018(2) 0.023(3) 0.0058(18) 0.0060(19) 0.0081(18) C5 0.021(2) 0.021(2) 0.032(3) 0.0070(19) 0.0077(19) 0.0024(18) C6 0.020(2) 0.021(2) 0.023(2) 0.0038(18) 0.0022(18) -0.0004(17) C7 0.023(2) 0.024(2) 0.026(3) -0.0004(19) -0.0008(19) 0.0065(19) C8 0.028(2) 0.034(3) 0.032(3) 0.003(2) -0.001(2) -0.001(2) C9 0.044(3) 0.041(3) 0.030(3) 0.001(2) -0.009(2) 0.004(3) C10 0.030(3) 0.039(3) 0.047(4) -0.008(3) -0.012(2) -0.004(2) C11 0.026(2) 0.031(3) 0.044(3) 0.000(2) -0.001(2) -0.004(2) C12 0.021(2) 0.028(2) 0.023(3) 0.0013(19) 0.0040(18) 0.0041(18) C13 0.019(2) 0.026(2) 0.037(3) 0.005(2) 0.0066(19) 0.0002(19) C14 0.023(2) 0.019(2) 0.022(2) 0.0061(18) 0.0011(18) 0.0008(17) C15 0.028(2) 0.021(2) 0.024(3) 0.0021(19) 0.0012(19) 0.0011(19) C16 0.025(2) 0.024(2) 0.023(3) 0.0051(19) 0.0012(19) 0.0036(19) C17 0.024(2) 0.020(2) 0.018(2) 0.0036(18) -0.0023(18) 0.0031(18) C18 0.032(2) 0.025(2) 0.020(3) 0.0058(19) -0.001(2) 0.001(2) C19 0.033(2) 0.017(2) 0.024(3) 0.0037(18) 0.013(2) 0.0059(19) C20 0.026(2) 0.021(2) 0.025(3) -0.0002(19) -0.0041(19) -0.0001(18) C21 0.021(2) 0.018(2) 0.028(3) -0.0023(18) -0.0005(19) 0.0010(18) C22 0.025(2) 0.024(2) 0.037(3) 0.001(2) 0.001(2) 0.0024(19) C23 0.025(2) 0.038(3) 0.046(3) 0.008(2) 0.010(2) 0.004(2) C24 0.030(2) 0.040(3) 0.041(3) 0.014(2) 0.011(2) 0.003(2) C25 0.030(2) 0.035(3) 0.034(3) 0.012(2) 0.005(2) 0.006(2) C26 0.024(2) 0.021(2) 0.028(3) -0.0038(19) 0.0010(19) 0.0025(18) C27 0.019(2) 0.017(2) 0.026(3) 0.0034(18) -0.0012(18) -0.0006(17) C28 0.020(2) 0.015(2) 0.023(2) 0.0002(17) 0.0025(18) -0.0024(17) C29 0.024(2) 0.019(2) 0.023(3) 0.0008(18) -0.0006(19) -0.0028(18) C30 0.022(2) 0.016(2) 0.029(3) 0.0078(18) -0.0027(19) -0.0023(17) C31 0.025(2) 0.018(2) 0.021(2) 0.0032(18) 0.0037(18) 0.0033(18) C32 0.019(2) 0.020(2) 0.020(2) 0.0045(18) 0.0003(17) -0.0038(17) C33 0.019(2) 0.016(2) 0.025(3) 0.0006(17) -0.0043(18) 0.0063(17) C34 0.029(2) 0.023(2) 0.032(3) -0.001(2) -0.004(2) 0.0010(19) C35 0.047(3) 0.025(3) 0.036(3) -0.010(2) -0.013(3) 0.000(2) C36 0.055(3) 0.030(3) 0.024(3) -0.004(2) -0.009(3) 0.006(2) C37 0.044(3) 0.025(2) 0.024(3) 0.001(2) 0.005(2) 0.005(2) C38 0.033(2) 0.017(2) 0.021(2) -0.0021(18) 0.001(2) 0.0041(19) C39 0.025(2) 0.020(2) 0.027(3) -0.0027(19) 0.0086(19) 0.0064(18) C40 0.026(2) 0.016(2) 0.020(2) 0.0022(17) 0.0094(18) -0.0020(17) C41 0.026(2) 0.019(2) 0.025(3) 0.0003(18) 0.0000(19) -0.0011(18) C42 0.021(2) 0.014(2) 0.027(3) 0.0008(18) 0.0022(18) 0.0000(17) C43 0.025(2) 0.012(2) 0.026(3) -0.0027(17) 0.0079(18) -0.0020(17) C44 0.023(2) 0.021(2) 0.022(2) 0.0017(18) 0.0008(18) -0.0038(18) C45 0.019(2) 0.014(2) 0.026(3) 0.0024(17) 0.0027(18) -0.0013(16) C46 0.025(2) 0.026(2) 0.018(2) 0.0009(18) 0.0039(18) 0.0026(19) C47 0.024(2) 0.023(2) 0.017(2) 0.0051(18) 0.0008(18) 0.0012(18) C48 0.033(2) 0.024(2) 0.022(3) 0.0034(19) 0.006(2) 0.0062(19) C49 0.025(2) 0.036(3) 0.027(3) 0.007(2) 0.008(2) 0.009(2) C50 0.021(2) 0.032(3) 0.033(3) 0.013(2) 0.001(2) 0.001(2) C51 0.023(2) 0.027(2) 0.029(3) 0.008(2) -0.001(2) 0.0014(19) C52 0.024(2) 0.022(2) 0.017(2) 0.0044(18) 0.0029(18) 0.0041(18) _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 2.100(4) . ? I2 C16 2.090(5) . ? I3 C19 2.090(5) . ? I4 C27 2.120(4) . ? I5 C42 2.094(4) . ? I6 C45 2.104(4) . ? Br1 C4 1.886(5) . ? Br2 C30 1.895(4) . ? O1 C14 1.377(5) . ? O1 C13 1.459(5) . ? O2 C17 1.378(5) . ? O2 C20 1.449(5) . ? O3 C40 1.377(5) . ? O3 C39 1.458(5) . ? O4 C43 1.368(5) . ? O4 C46 1.456(5) . ? C1 C6 1.409(6) . ? C1 C2 1.414(6) . ? C2 C3 1.392(6) . ? C2 C26 1.495(6) . ? C3 C4 1.386(6) . ? C3 H3 0.9500 . ? C4 C5 1.389(6) . ? C5 C6 1.389(6) . ? C5 H5 0.9500 . ? C6 C7 1.503(6) . ? C7 C8 1.390(7) . ? C7 C12 1.417(7) . ? C8 C9 1.390(7) . ? C8 H8 0.9500 . ? C9 C10 1.391(8) . ? C9 H9 0.9500 . ? C10 C11 1.385(8) . ? C10 H10 0.9500 . ? C11 C12 1.399(7) . ? C11 H11 0.9500 . ? C12 C13 1.496(7) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.393(6) . ? C14 C19 1.407(6) . ? C15 C16 1.391(6) . ? C15 H15 0.9500 . ? C16 C17 1.393(6) . ? C17 C18 1.384(6) . ? C18 C19 1.388(6) . ? C18 H18 0.9500 . ? C20 C21 1.508(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.390(6) . ? C21 C26 1.419(6) . ? C22 C23 1.373(7) . ? C22 H22 0.9500 . ? C23 C24 1.389(7) . ? C23 H23 0.9500 . ? C24 C25 1.380(7) . ? C24 H24 0.9500 . ? C25 C26 1.384(7) . ? C25 H25 0.9500 . ? C27 C32 1.394(6) . ? C27 C28 1.407(6) . ? C28 C29 1.389(6) . ? C28 C52 1.497(6) . ? C29 C30 1.365(6) . ? C29 H29 0.9500 . ? C30 C31 1.384(7) . ? C31 C32 1.401(6) . ? C31 H31 0.9500 . ? C32 C33 1.504(6) . ? C33 C38 1.399(6) . ? C33 C34 1.406(6) . ? C34 C35 1.384(7) . ? C34 H34 0.9500 . ? C35 C36 1.377(8) . ? C35 H35 0.9500 . ? C36 C37 1.389(7) . ? C36 H36 0.9500 . ? C37 C38 1.405(7) . ? C37 H37 0.9500 . ? C38 C39 1.509(6) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C45 1.394(6) . ? C40 C41 1.396(6) . ? C41 C42 1.386(6) . ? C41 H41 0.9500 . ? C42 C43 1.395(6) . ? C43 C44 1.375(6) . ? C44 C45 1.364(6) . ? C44 H44 0.9500 . ? C46 C47 1.519(6) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C52 1.396(6) . ? C47 C48 1.406(6) . ? C48 C49 1.385(7) . ? C48 H48 0.9500 . ? C49 C50 1.385(7) . ? C49 H49 0.9500 . ? C50 C51 1.376(7) . ? C50 H50 0.9500 . ? C51 C52 1.399(6) . ? C51 H51 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 C14 O1 C13 114.0(3) . . ? C17 O2 C20 116.8(3) . . ? C40 O3 C39 116.2(3) . . ? C43 O4 C46 114.9(3) . . ? C6 C1 C2 121.2(4) . . ? C6 C1 I1 120.8(3) . . ? C2 C1 I1 117.9(3) . . ? C3 C2 C1 118.7(4) . . ? C3 C2 C26 119.4(4) . . ? C1 C2 C26 121.8(4) . . ? C4 C3 C2 120.2(4) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.7(4) . . ? C3 C4 Br1 119.7(3) . . ? C5 C4 Br1 119.6(3) . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 118.0(4) . . ? C5 C6 C7 119.6(4) . . ? C1 C6 C7 122.2(4) . . ? C8 C7 C12 118.3(4) . . ? C8 C7 C6 117.9(4) . . ? C12 C7 C6 123.8(4) . . ? C9 C8 C7 122.5(5) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C10 119.1(5) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 119.4(5) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 122.0(5) . . ? C10 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? C11 C12 C7 118.6(4) . . ? C11 C12 C13 116.7(4) . . ? C7 C12 C13 124.5(4) . . ? O1 C13 C12 114.5(4) . . ? O1 C13 H13A 108.6 . . ? C12 C13 H13A 108.6 . . ? O1 C13 H13B 108.6 . . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? O1 C14 C15 117.9(4) . . ? O1 C14 C19 123.1(4) . . ? C15 C14 C19 118.8(4) . . ? C16 C15 C14 120.8(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.7(4) . . ? C15 C16 I2 120.1(3) . . ? C17 C16 I2 120.2(3) . . ? O2 C17 C18 122.4(4) . . ? O2 C17 C16 118.4(4) . . ? C18 C17 C16 119.0(4) . . ? C17 C18 C19 121.4(4) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C14 119.2(4) . . ? C18 C19 I3 117.5(3) . . ? C14 C19 I3 123.3(3) . . ? O2 C20 C21 111.4(4) . . ? O2 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? O2 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C26 117.8(4) . . ? C22 C21 C20 118.0(4) . . ? C26 C21 C20 124.1(4) . . ? C23 C22 C21 122.8(4) . . ? C23 C22 H22 118.6 . . ? C21 C22 H22 118.6 . . ? C22 C23 C24 118.6(5) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C25 C24 C23 120.1(5) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 121.4(5) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C25 C26 C21 119.0(4) . . ? C25 C26 C2 118.5(4) . . ? C21 C26 C2 122.6(4) . . ? C32 C27 C28 121.5(4) . . ? C32 C27 I4 119.9(3) . . ? C28 C27 I4 118.6(3) . . ? C29 C28 C27 117.9(4) . . ? C29 C28 C52 117.8(4) . . ? C27 C28 C52 124.1(4) . . ? C30 C29 C28 121.2(4) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C29 C30 C31 121.1(4) . . ? C29 C30 Br2 118.7(4) . . ? C31 C30 Br2 120.1(3) . . ? C30 C31 C32 119.7(4) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C27 C32 C31 118.6(4) . . ? C27 C32 C33 123.9(4) . . ? C31 C32 C33 117.5(4) . . ? C38 C33 C34 118.8(4) . . ? C38 C33 C32 122.7(4) . . ? C34 C33 C32 118.5(4) . . ? C35 C34 C33 121.1(5) . . ? C35 C34 H34 119.4 . . ? C33 C34 H34 119.4 . . ? C36 C35 C34 119.9(5) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C37 120.2(5) . . ? C35 C36 H36 119.9 . . ? C37 C36 H36 119.9 . . ? C36 C37 C38 120.5(5) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C33 C38 C37 119.4(4) . . ? C33 C38 C39 124.0(4) . . ? C37 C38 C39 116.5(4) . . ? O3 C39 C38 112.7(3) . . ? O3 C39 H39A 109.1 . . ? C38 C39 H39A 109.1 . . ? O3 C39 H39B 109.1 . . ? C38 C39 H39B 109.1 . . ? H39A C39 H39B 107.8 . . ? O3 C40 C45 123.8(4) . . ? O3 C40 C41 117.9(4) . . ? C45 C40 C41 118.1(4) . . ? C42 C41 C40 120.6(4) . . ? C42 C41 H41 119.7 . . ? C40 C41 H41 119.7 . . ? C41 C42 C43 119.9(4) . . ? C41 C42 I5 121.1(3) . . ? C43 C42 I5 118.9(3) . . ? O4 C43 C44 122.4(4) . . ? O4 C43 C42 119.2(4) . . ? C44 C43 C42 118.3(4) . . ? C45 C44 C43 121.8(4) . . ? C45 C44 H44 119.1 . . ? C43 C44 H44 119.1 . . ? C44 C45 C40 120.3(4) . . ? C44 C45 I6 118.2(3) . . ? C40 C45 I6 121.4(3) . . ? O4 C46 C47 113.6(3) . . ? O4 C46 H46A 108.8 . . ? C47 C46 H46A 108.8 . . ? O4 C46 H46B 108.8 . . ? C47 C46 H46B 108.8 . . ? H46A C46 H46B 107.7 . . ? C52 C47 C48 117.9(4) . . ? C52 C47 C46 125.0(4) . . ? C48 C47 C46 117.0(4) . . ? C49 C48 C47 121.9(4) . . ? C49 C48 H48 119.0 . . ? C47 C48 H48 119.0 . . ? C50 C49 C48 119.4(4) . . ? C50 C49 H49 120.3 . . ? C48 C49 H49 120.3 . . ? C51 C50 C49 119.6(4) . . ? C51 C50 H50 120.2 . . ? C49 C50 H50 120.2 . . ? C50 C51 C52 121.5(5) . . ? C50 C51 H51 119.3 . . ? C52 C51 H51 119.3 . . ? C47 C52 C51 119.6(4) . . ? C47 C52 C28 123.2(4) . . ? C51 C52 C28 117.0(4) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.821 _refine_diff_density_min -1.144 _refine_diff_density_rms 0.141 # Attachment 'Compound-2-pub.cif.txt' data_briodoterphenyl _database_code_depnum_ccdc_archive 'CCDC 768763' #TrackingRef 'Compound-2-pub.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 Br5 I' _chemical_formula_sum 'C20 H12 Br5 I' _chemical_formula_weight 778.75 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.327(2) _cell_length_b 10.367(2) _cell_length_c 11.470(2) _cell_angle_alpha 68.30(3) _cell_angle_beta 75.05(3) _cell_angle_gamma 76.79(3) _cell_volume 1090.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3689 _cell_measurement_theta_min 2.6500 _cell_measurement_theta_max 26.3981 _exptl_crystal_description chip _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 10.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0812 _exptl_absorpt_correction_T_max 0.2254 _exptl_absorpt_process_details 'REQAB, Rigaku/MSC, The Woodlands, TX, USA, 1999.' _exptl_special_details ? _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_measurement_method omega _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 260 Slice: -40.0000 - 90.0000 Image width: 0.5000 Exp time: 15.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 27.6736 2theta: -0.2907 scan: Number of images: 260 Slice: -40.0000 - 80.0000 Image width: 0.5000 Exp time: 15.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 27.6736 2theta: -0.2907 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3 circle ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8438 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3862 _reflns_number_gt 3481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC,2001)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC,2001)' _computing_data_reduction 'CrystalClear (Rigaku/MSC,2001)' _computing_structure_solution 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_structure_refinement 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_molecular_graphics 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_publication_material 'SHELXTL 6.10 (Bruker AXS,2000)' _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^)+(0.0373P)^2^+3.0696P] 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 3862 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.08049(3) 0.94625(3) 0.18609(3) 0.03097(11) Uani 1 1 d . . . Br1 Br 0.57153(5) 0.38854(5) 0.31318(7) 0.04463(17) Uani 1 1 d . . . Br2 Br -0.19987(5) 0.57113(6) 0.40623(5) 0.03894(15) Uani 1 1 d . . . Br3 Br 0.05767(5) 0.34754(5) 0.36311(5) 0.03552(14) Uani 1 1 d . . . Br4 Br 0.44808(6) 1.20674(5) 0.05359(5) 0.03601(14) Uani 1 1 d . . . Br5 Br 0.66339(6) 0.94739(6) 0.16906(6) 0.04310(15) Uani 1 1 d . . . C1 C 0.2302(4) 0.7713(4) 0.2291(4) 0.0215(9) Uani 1 1 d . . . C2 C 0.3248(4) 0.7692(4) 0.2986(4) 0.0199(9) Uani 1 1 d . . . C3 C 0.4281(5) 0.6554(5) 0.3205(4) 0.0233(9) Uani 1 1 d . . . H3 H 0.4940 0.6521 0.3665 0.028 Uiso 1 1 calc R . . C4 C 0.4344(4) 0.5459(5) 0.2746(5) 0.0258(10) Uani 1 1 d . . . C5 C 0.3402(4) 0.5471(4) 0.2082(4) 0.0228(9) Uani 1 1 d . . . H5 H 0.3463 0.4711 0.1787 0.027 Uiso 1 1 calc R . . C6 C 0.2364(4) 0.6596(4) 0.1844(4) 0.0207(9) Uani 1 1 d . . . C7 C 0.1345(4) 0.6600(4) 0.1123(4) 0.0218(9) Uani 1 1 d . . . C8 C 0.1645(5) 0.7049(5) -0.0213(4) 0.0274(10) Uani 1 1 d . . . H8 H 0.2506 0.7323 -0.0652 0.033 Uiso 1 1 calc R . . C9 C 0.0713(5) 0.7101(5) -0.0895(5) 0.0294(10) Uani 1 1 d . . . H9 H 0.0935 0.7406 -0.1803 0.035 Uiso 1 1 calc R . . C10 C -0.0555(5) 0.6712(5) -0.0272(5) 0.0286(10) Uani 1 1 d . . . H10 H -0.1209 0.6775 -0.0748 0.034 Uiso 1 1 calc R . . C11 C -0.0853(5) 0.6232(5) 0.1049(4) 0.0258(10) Uani 1 1 d . . . H11 H -0.1713 0.5952 0.1481 0.031 Uiso 1 1 calc R . . C12 C 0.0093(4) 0.6156(5) 0.1754(4) 0.0224(9) Uani 1 1 d . . . C13 C -0.0132(5) 0.5496(5) 0.3185(4) 0.0269(10) Uani 1 1 d . . . H13 H 0.0401 0.5934 0.3515 0.032 Uiso 1 1 calc R . . C14 C 0.4713(5) 1.0119(5) 0.1654(4) 0.0282(10) Uani 1 1 d . . . H14 H 0.4402 0.9539 0.1279 0.034 Uiso 1 1 calc R . . C15 C 0.3896(5) 0.9923(5) 0.2976(4) 0.0243(9) Uani 1 1 d . . . C16 C 0.3846(5) 1.0844(5) 0.3617(5) 0.0313(11) Uani 1 1 d . . . H16 H 0.4347 1.1609 0.3217 0.038 Uiso 1 1 calc R . . C17 C 0.3072(6) 1.0657(5) 0.4837(5) 0.0346(11) Uani 1 1 d . . . H17 H 0.3049 1.1287 0.5270 0.041 Uiso 1 1 calc R . . C18 C 0.2340(6) 0.9563(5) 0.5413(5) 0.0376(12) Uani 1 1 d . . . H18 H 0.1799 0.9442 0.6242 0.045 Uiso 1 1 calc R . . C19 C 0.2386(5) 0.8637(5) 0.4793(5) 0.0317(11) Uani 1 1 d . . . H19 H 0.1879 0.7878 0.5208 0.038 Uiso 1 1 calc R . . C20 C 0.3161(4) 0.8788(4) 0.3564(4) 0.0207(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02926(18) 0.02369(17) 0.04038(19) -0.01420(13) -0.00905(13) 0.00409(12) Br1 0.0328(3) 0.0286(3) 0.0885(5) -0.0323(3) -0.0299(3) 0.0074(2) Br2 0.0268(3) 0.0604(4) 0.0354(3) -0.0223(2) 0.0023(2) -0.0159(2) Br3 0.0420(3) 0.0312(3) 0.0304(3) 0.0007(2) -0.0115(2) -0.0131(2) Br4 0.0472(3) 0.0317(3) 0.0273(2) -0.0053(2) -0.0006(2) -0.0172(2) Br5 0.0339(3) 0.0440(3) 0.0458(3) -0.0174(2) 0.0079(2) -0.0082(2) C1 0.017(2) 0.016(2) 0.029(2) -0.0047(17) -0.0021(17) -0.0058(16) C2 0.019(2) 0.018(2) 0.022(2) -0.0088(17) 0.0043(16) -0.0071(16) C3 0.022(2) 0.021(2) 0.032(2) -0.0122(18) -0.0045(18) -0.0082(17) C4 0.020(2) 0.019(2) 0.042(3) -0.013(2) -0.0073(19) -0.0038(17) C5 0.020(2) 0.017(2) 0.034(2) -0.0117(18) -0.0018(18) -0.0061(17) C6 0.017(2) 0.018(2) 0.025(2) -0.0065(17) 0.0023(17) -0.0058(16) C7 0.024(2) 0.018(2) 0.027(2) -0.0107(17) -0.0067(18) -0.0022(17) C8 0.030(2) 0.021(2) 0.029(2) -0.0056(18) -0.0011(19) -0.0096(19) C9 0.035(3) 0.021(2) 0.027(2) -0.0039(19) -0.006(2) -0.0003(19) C10 0.033(3) 0.023(2) 0.032(2) -0.0084(19) -0.014(2) -0.0004(19) C11 0.024(2) 0.025(2) 0.031(2) -0.0129(19) -0.0064(19) -0.0014(18) C12 0.024(2) 0.021(2) 0.025(2) -0.0098(18) -0.0032(18) -0.0066(17) C13 0.024(2) 0.031(2) 0.028(2) -0.0094(19) -0.0015(19) -0.0132(19) C14 0.036(3) 0.030(2) 0.025(2) -0.0128(19) 0.003(2) -0.020(2) C15 0.029(2) 0.019(2) 0.025(2) -0.0081(18) -0.0011(19) -0.0079(18) C16 0.041(3) 0.024(2) 0.031(2) -0.012(2) -0.001(2) -0.012(2) C17 0.048(3) 0.031(3) 0.029(2) -0.019(2) -0.006(2) 0.000(2) C18 0.046(3) 0.031(3) 0.028(2) -0.015(2) 0.010(2) -0.002(2) C19 0.031(3) 0.025(2) 0.033(3) -0.010(2) 0.008(2) -0.009(2) C20 0.018(2) 0.017(2) 0.025(2) -0.0061(17) -0.0016(17) -0.0025(16) _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 2.091(4) . ? Br1 C4 1.896(5) . ? Br2 C13 1.936(5) . ? Br3 C13 1.971(5) . ? Br4 C14 1.950(5) . ? Br5 C14 1.949(5) . ? C1 C2 1.403(6) . ? C1 C6 1.412(6) . ? C2 C3 1.392(6) . ? C2 C20 1.490(6) . ? C3 C4 1.400(6) . ? C3 H3 0.9500 . ? C4 C5 1.377(7) . ? C5 C6 1.389(6) . ? C5 H5 0.9500 . ? C6 C7 1.495(6) . ? C7 C12 1.396(6) . ? C7 C8 1.398(6) . ? C8 C9 1.370(7) . ? C8 H8 0.9500 . ? C9 C10 1.391(7) . ? C9 H9 0.9500 . ? C10 C11 1.382(7) . ? C10 H10 0.9500 . ? C11 C12 1.393(6) . ? C11 H11 0.9500 . ? C12 C13 1.504(6) . ? C13 H13 1.0000 . ? C14 C15 1.497(6) . ? C14 H14 1.0000 . ? C15 C16 1.390(7) . ? C15 C20 1.405(6) . ? C16 C17 1.388(7) . ? C16 H16 0.9500 . ? C17 C18 1.369(8) . ? C17 H17 0.9500 . ? C18 C19 1.377(7) . ? C18 H18 0.9500 . ? C19 C20 1.401(6) . ? C19 H19 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 121.4(4) . . ? C2 C1 I1 119.2(3) . . ? C6 C1 I1 119.3(3) . . ? C3 C2 C1 118.6(4) . . ? C3 C2 C20 118.0(4) . . ? C1 C2 C20 123.3(4) . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 121.7(4) . . ? C5 C4 Br1 119.7(3) . . ? C3 C4 Br1 118.5(4) . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 118.8(4) . . ? C5 C6 C7 119.5(4) . . ? C1 C6 C7 121.7(4) . . ? C12 C7 C8 118.8(4) . . ? C12 C7 C6 121.5(4) . . ? C8 C7 C6 119.7(4) . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.6(4) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 119.2(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C7 119.8(4) . . ? C11 C12 C13 122.3(4) . . ? C7 C12 C13 117.7(4) . . ? C12 C13 Br2 115.2(3) . . ? C12 C13 Br3 109.3(3) . . ? Br2 C13 Br3 108.4(2) . . ? C12 C13 H13 107.9 . . ? Br2 C13 H13 107.9 . . ? Br3 C13 H13 107.9 . . ? C15 C14 Br5 111.0(3) . . ? C15 C14 Br4 112.5(3) . . ? Br5 C14 Br4 109.0(2) . . ? C15 C14 H14 108.0 . . ? Br5 C14 H14 108.0 . . ? Br4 C14 H14 108.0 . . ? C16 C15 C20 119.9(4) . . ? C16 C15 C14 121.3(4) . . ? C20 C15 C14 118.7(4) . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 119.9(5) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 121.6(4) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C19 C20 C15 117.8(4) . . ? C19 C20 C2 118.9(4) . . ? C15 C20 C2 123.1(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.210 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.127 # Attachment 'Compound-4-pub.cif.txt' data_ohterphenyl _database_code_depnum_ccdc_archive 'CCDC 768764' #TrackingRef 'Compound-4-pub.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Br I O2' _chemical_formula_sum 'C20 H16 Br I O2' _chemical_formula_weight 495.14 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4/m _symmetry_space_group_name_hall I4/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z' 'y, -x, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z' '-y, x, -z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 21.861(3) _cell_length_b 21.861(3) _cell_length_c 16.153(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7720(2) _cell_formula_units_Z 16 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7733 _cell_measurement_theta_min 3.5880 _cell_measurement_theta_max 26.0127 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3840 _exptl_absorpt_coefficient_mu 3.738 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2670 _exptl_absorpt_correction_T_max 0.8351 _exptl_absorpt_process_details 'REQAB, Rigaku/MSC, The Woodlands, TX, USA, 1999.' _exptl_special_details ? _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6306 _diffrn_measurement_method omega _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 260 Slice: -40.0000 - 90.0000 Image width: 0.5000 Exp time: 45.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 37.8385 2theta: 7.4975 scan: Number of images: 200 Slice: -40.0000 - 80.0000 Image width: 0.5000 Exp time: 45.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 37.8385 2theta: 7.4975 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3 circle ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13542 _diffrn_reflns_av_R_equivalents 0.1198 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3562 _reflns_number_gt 2777 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC,2001)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC,2001)' _computing_data_reduction 'CrystalClear (Rigaku/MSC,2001)' _computing_structure_solution 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_structure_refinement 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_molecular_graphics 'SHELXTL 6.10 (Bruker AXS,2000)' _computing_publication_material 'SHELXTL 6.10 (Bruker AXS,2000)' _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^)+(0.0893P)^2^+49.6358P] 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 3562 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1795 _refine_ls_wR_factor_gt 0.1660 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.35958(3) 0.20539(4) 0.0000 0.0488(3) Uani 1 2 d S . . Br1' Br 0.66814(5) 0.21775(5) 0.0000 0.0442(3) Uani 1 2 d S . . C1' C 0.4577(5) 0.2045(5) 0.0000 0.040(2) Uani 1 2 d S . . O1' O 0.5010(8) 0.0680(9) 0.135(2) 0.170(19) Uani 0.46(3) 1 d P . . C2' C 0.4869(3) 0.2047(3) 0.0762(4) 0.0361(15) Uani 1 1 d . . . C3' C 0.5507(3) 0.2088(3) 0.0748(4) 0.0390(16) Uani 1 1 d . . . H3' H 0.5729 0.2101 0.1254 0.027(16) Uiso 1 1 calc R . . O1'A O 0.4562(17) 0.0371(8) 0.1874(12) 0.167(15) Uani 0.54(3) 1 d P . . C4' C 0.5820(4) 0.2109(5) 0.0000 0.038(2) Uani 1 2 d S . . C5' C 0.4543(3) 0.2010(4) 0.1584(4) 0.0436(17) Uani 1 1 d . . . C6' C 0.4424(4) 0.2539(4) 0.2028(5) 0.052(2) Uani 1 1 d . . . H6' H 0.4553 0.2927 0.1825 0.06(3) Uiso 1 1 calc R . . C7' C 0.4113(4) 0.2491(6) 0.2778(6) 0.070(3) Uani 1 1 d . . . H7' H 0.4019 0.2853 0.3077 0.12(5) Uiso 1 1 calc R . . C8' C 0.3941(4) 0.1943(7) 0.3093(5) 0.083(4) Uani 1 1 d . . . H8' H 0.3725 0.1916 0.3602 0.08(3) Uiso 1 1 calc R . . C9' C 0.4089(4) 0.1427(6) 0.2651(6) 0.070(3) Uani 1 1 d . . . H9' H 0.3986 0.1040 0.2881 0.05(2) Uiso 1 1 calc R . . C10' C 0.4376(4) 0.1438(5) 0.1897(5) 0.056(2) Uani 1 1 d . . . C11' C 0.4480(5) 0.0867(5) 0.1399(7) 0.077(3) Uani 1 1 d . . . I1 I 0.84633(4) 0.82840(3) 0.0000 0.0514(3) Uani 1 2 d S . . Br1 Br 0.62036(6) 1.03897(6) 0.0000 0.0561(4) Uani 1 2 d S . . C1 C 0.7781(5) 0.8976(5) 0.0000 0.046(3) Uani 1 2 d S . . O1 O 0.9148(4) 0.9923(5) 0.1915(9) 0.130(4) Uani 1 1 d . . . H1 H 0.9457 0.9889 0.1609 0.195 Uiso 1 1 calc R . . C2 C 0.7570(4) 0.9186(3) 0.0760(5) 0.0428(17) Uani 1 1 d . . . C3 C 0.7083(4) 0.9621(3) 0.0751(5) 0.0462(18) Uani 1 1 d . . . H3 H 0.6918 0.9769 0.1256 0.055 Uiso 1 1 calc R . . C4 C 0.6851(5) 0.9828(5) 0.0000 0.047(3) Uani 1 2 d S . . C5 C 0.7795(4) 0.8971(4) 0.1572(5) 0.0491(19) Uani 1 1 d . . . C6 C 0.7502(4) 0.8513(4) 0.1999(5) 0.0499(19) Uani 1 1 d . . . H6 H 0.7151 0.8327 0.1758 0.060 Uiso 1 1 calc R . . C7 C 0.7701(4) 0.8306(5) 0.2784(5) 0.059(2) Uani 1 1 d . . . H7 H 0.7494 0.7985 0.3063 0.071 Uiso 1 1 calc R . . C8 C 0.8194(4) 0.8580(5) 0.3126(5) 0.062(2) Uani 1 1 d . . . H8 H 0.8336 0.8446 0.3652 0.075 Uiso 1 1 calc R . . C9 C 0.8502(4) 0.9056(5) 0.2725(6) 0.064(2) Uani 1 1 d . . . H9 H 0.8841 0.9248 0.2985 0.077 Uiso 1 1 calc R . . C10 C 0.8313(4) 0.9250(4) 0.1948(5) 0.055(2) Uani 1 1 d . . . C11 C 0.8639(5) 0.9749(5) 0.1490(8) 0.079(3) Uani 1 1 d . . . H11A H 0.8757 0.9602 0.0933 0.094 Uiso 1 1 calc R . . H11B H 0.8363 1.0105 0.1421 0.094 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' 0.0337(4) 0.0756(6) 0.0372(4) 0.000 0.000 0.0034(3) Br1' 0.0358(5) 0.0635(7) 0.0333(5) 0.000 0.000 -0.0052(5) C1' 0.034(5) 0.050(6) 0.037(5) 0.000 0.000 0.002(4) O1' 0.054(11) 0.067(13) 0.39(5) -0.06(2) 0.065(18) 0.012(8) C2' 0.035(4) 0.040(4) 0.033(4) -0.006(3) -0.002(3) 0.008(3) C3' 0.037(4) 0.045(4) 0.035(4) 0.001(3) -0.004(3) 0.005(3) O1'A 0.36(4) 0.067(11) 0.074(12) 0.027(9) -0.031(17) -0.032(16) C4' 0.030(5) 0.052(6) 0.031(5) 0.000 0.000 -0.001(4) C5' 0.036(4) 0.062(5) 0.033(4) 0.008(3) 0.002(3) 0.003(3) C6' 0.049(5) 0.074(6) 0.035(4) -0.009(4) 0.005(3) 0.014(4) C7' 0.052(5) 0.122(9) 0.036(4) -0.014(6) 0.004(4) 0.025(6) C8' 0.051(5) 0.173(13) 0.026(4) 0.034(6) 0.009(4) 0.031(7) C9' 0.041(5) 0.115(8) 0.054(5) 0.041(6) 0.011(4) 0.017(5) C10' 0.048(5) 0.080(6) 0.039(4) 0.013(4) 0.003(4) 0.008(4) C11' 0.102(8) 0.061(6) 0.068(6) 0.015(5) 0.011(6) 0.022(6) I1 0.0641(5) 0.0473(4) 0.0427(4) 0.000 0.000 0.0137(3) Br1 0.0634(8) 0.0523(7) 0.0526(7) 0.000 0.000 0.0193(6) C1 0.055(6) 0.031(5) 0.052(6) 0.000 0.000 0.000(5) O1 0.083(6) 0.101(7) 0.206(13) 0.000(8) -0.024(7) -0.005(6) C2 0.045(4) 0.041(4) 0.042(4) 0.000(3) 0.002(3) 0.003(3) C3 0.059(5) 0.041(4) 0.038(4) -0.011(3) 0.006(4) 0.002(4) C4 0.047(6) 0.043(6) 0.052(7) 0.000 0.000 0.004(5) C5 0.049(4) 0.054(5) 0.045(4) -0.006(4) 0.001(4) 0.014(4) C6 0.062(5) 0.048(4) 0.040(4) 0.000(3) 0.005(4) 0.005(4) C7 0.062(5) 0.072(6) 0.042(4) 0.006(4) 0.005(4) 0.027(5) C8 0.056(5) 0.096(7) 0.034(4) 0.004(4) 0.003(4) 0.023(5) C9 0.054(5) 0.084(7) 0.053(5) -0.006(5) -0.012(4) 0.007(5) C10 0.041(4) 0.075(6) 0.050(5) -0.001(4) 0.001(4) 0.011(4) C11 0.053(5) 0.085(7) 0.097(8) -0.010(7) -0.017(6) -0.002(5) _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' 2.145(10) . ? Br1' C4' 1.890(10) . ? C1' C2' 1.387(8) . ? C1' C2' 1.387(8) 10 ? O1' C11' 1.231(18) . ? C2' C3' 1.398(10) . ? C2' C5' 1.509(10) . ? C3' C4' 1.389(8) . ? C3' H3' 0.9500 . ? O1'A C11' 1.341(19) . ? C4' C3' 1.389(8) 10 ? C5' C6' 1.385(11) . ? C5' C10' 1.398(12) . ? C6' C7' 1.393(12) . ? C6' H6' 0.9500 . ? C7' C8' 1.356(17) . ? C7' H7' 0.9500 . ? C8' C9' 1.374(17) . ? C8' H8' 0.9500 . ? C9' C10' 1.371(12) . ? C9' H9' 0.9500 . ? C10' C11' 1.503(14) . ? I1 C1 2.125(11) . ? Br1 C4 1.875(11) . ? C1 C2 1.389(9) 10 ? C1 C2 1.389(9) . ? O1 C11 1.361(13) . ? O1 H1 0.8400 . ? C2 C3 1.429(11) . ? C2 C5 1.478(11) . ? C3 C4 1.389(9) . ? C3 H3 0.9500 . ? C4 C3 1.389(9) 10 ? C5 C6 1.375(12) . ? C5 C10 1.423(12) . ? C6 C7 1.414(12) . ? C6 H6 0.9500 . ? C7 C8 1.351(14) . ? C7 H7 0.9500 . ? C8 C9 1.398(14) . ? C8 H8 0.9500 . ? C9 C10 1.386(13) . ? C9 H9 0.9500 . ? C10 C11 1.500(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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' 125.2(9) . 10 ? C2' C1' I1' 117.4(5) . . ? C2' C1' I1' 117.4(5) 10 . ? C1' C2' C3' 116.4(7) . . ? C1' C2' C5' 124.3(6) . . ? C3' C2' C5' 119.3(6) . . ? C4' C3' C2' 120.5(7) . . ? C4' C3' H3' 119.8 . . ? C2' C3' H3' 119.8 . . ? C3' C4' C3' 120.9(9) 10 . ? C3' C4' Br1' 119.5(4) 10 . ? C3' C4' Br1' 119.5(4) . . ? C6' C5' C10' 120.7(7) . . ? C6' C5' C2' 119.9(7) . . ? C10' C5' C2' 119.3(7) . . ? C5' C6' C7' 118.6(9) . . ? C5' C6' H6' 120.7 . . ? C7' C6' H6' 120.7 . . ? C8' C7' C6' 121.9(10) . . ? C8' C7' H7' 119.0 . . ? C6' C7' H7' 119.0 . . ? C7' C8' C9' 117.7(8) . . ? C7' C8' H8' 121.1 . . ? C9' C8' H8' 121.1 . . ? C10' C9' C8' 123.7(10) . . ? C10' C9' H9' 118.1 . . ? C8' C9' H9' 118.1 . . ? C9' C10' C5' 117.2(9) . . ? C9' C10' C11' 122.0(9) . . ? C5' C10' C11' 120.7(7) . . ? O1' C11' O1'A 69(2) . . ? O1' C11' C10' 116.9(15) . . ? O1'A C11' C10' 112.7(12) . . ? C2 C1 C2 124.3(10) 10 . ? C2 C1 I1 117.9(5) 10 . ? C2 C1 I1 117.9(5) . . ? C11 O1 H1 109.5 . . ? C1 C2 C3 117.2(7) . . ? C1 C2 C5 124.8(7) . . ? C3 C2 C5 117.9(7) . . ? C4 C3 C2 119.8(7) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C3 121.5(10) . 10 ? C3 C4 Br1 119.2(5) . . ? C3 C4 Br1 119.2(5) 10 . ? C6 C5 C10 118.0(8) . . ? C6 C5 C2 121.5(8) . . ? C10 C5 C2 120.5(8) . . ? C5 C6 C7 122.5(9) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 118.1(9) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 C8 C9 121.6(8) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 120.3(9) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C5 119.5(9) . . ? C9 C10 C11 121.9(9) . . ? C5 C10 C11 118.7(8) . . ? O1 C11 C10 110.0(11) . . ? O1 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? O1 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.794 _refine_diff_density_min -1.750 _refine_diff_density_rms 0.182 # start Validation Reply Form _vrf_PLAT242_ohterphenyl ; PROBLEM: Check Low Ueq as Compared to Neighbors for C11' RESPONSE: The Low Ueq for C11' is due to neighbors O1' and O1'A exhibiting disorder ; _vrf_PLAT430_ohterphenyl ; PROBLEM: Short Inter D...A Contact O1'A .. O1'A .. 2.49 Ang. RESPONSE: The Short contact of O1'A is due to disorder in which hydrogen atoms were not located or refined ; # end Validation Reply Form # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 51 4 ' ' 2 0.500 0.500 0.000 353 52 ' ' 3 0.000 0.000 0.500 353 52 ' ' 4 0.500 0.500 0.500 51 4 ' ' _platon_squeeze_details ; ;