# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Kazutaka Shibatomi' _publ_contact_author_address ;Toyohashi University of Technology Hibarigaoka 1-1, Tempaku-cho, Toyohashi-shi, Japan ; _publ_contact_author_email shiba@ens.tut.ac.jp _publ_contact_author_phone +81(532)446810 _publ_contact_author_fax +81(532)485833 loop_ _publ_author_name _publ_author_address 'Kazutaka Shibatomi' ;Toyohashi University of Technology Hibarigaoka 1-1, Tempaku-cho, Toyohashi-shi, Japan ; 'Fumito Kobayashi' '' 'Akira Narayama' '' 'Ikuhide Fujisawa' '' 'Seiji Iwasa' '' data_shib32 _database_code_depnum_ccdc_archive 'CCDC 822839' #TrackingRef '- cif 18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 Br F3 O3' _chemical_formula_sum 'C21 H16 Br F3 O3' _chemical_formula_weight 453.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0606(18) _cell_length_b 12.444(3) _cell_length_c 21.593(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.260(2) _cell_angle_gamma 90.00 _cell_volume 1891.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295.00 _cell_measurement_reflns_used 5027 _cell_measurement_theta_min 2.5014 _cell_measurement_theta_max 30.3678 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6000 _exptl_crystal_size_mid 0.5000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.221 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3590 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ???? ; _diffrn_ambient_temperature 295.00 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_device_type ;4-circle diffractometer, Rigaku Mercury CCD camera(2x2 bin mode) ; _diffrn_measurement_method dtintegrate.ref _diffrn_detector_area_resol_mean 14.7059 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14279 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 29.13 _reflns_number_total 6814 _reflns_number_gt 5343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_structure_solution 'SIR 2004 (Burla, Caliandro et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _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^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0092(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.003(8) _refine_ls_number_reflns 6814 _refine_ls_number_parameters 634 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.6926(5) 0.1934(3) 0.81147(18) 0.0522(8) Uani 1 1 d . . . C2 C -0.6578(4) 0.1772(3) 0.87965(16) 0.0449(7) Uani 1 1 d . . . C3 C -0.5955(4) 0.0801(3) 0.90478(18) 0.0494(7) Uani 1 1 d . . . H3 H -0.572(5) 0.014(3) 0.8782(19) 0.048(9) Uiso 1 1 d . . . C4 C -0.5616(4) 0.0690(3) 0.96836(16) 0.0472(7) Uani 1 1 d . . . H4 H -0.538(7) -0.013(6) 0.985(3) 0.091(16) Uiso 1 1 d . . . C5 C -0.5818(4) 0.1551(3) 1.00860(16) 0.0430(6) Uani 1 1 d . . . C6 C -0.6451(5) 0.2523(3) 0.98217(17) 0.0512(8) Uani 1 1 d . . . H6 H -0.663(5) 0.303(4) 1.010(2) 0.060(11) Uiso 1 1 d . . . C7 C -0.6831(5) 0.2627(3) 0.91898(18) 0.0540(8) Uani 1 1 d . . . H7 H -0.729(5) 0.342(4) 0.907(2) 0.066(11) Uiso 1 1 d . . . C8 C -0.5436(4) 0.1428(3) 1.07638(16) 0.0439(7) Uani 1 1 d . . . C9 C -0.4139(5) 0.0670(3) 1.10105(18) 0.0554(9) Uani 1 1 d . . . H9 H -0.347(5) 0.021(3) 1.071(2) 0.051(10) Uiso 1 1 d . . . C10 C -0.3791(5) 0.0531(4) 1.16404(19) 0.0641(10) Uani 1 1 d . . . H10 H -0.293(7) -0.014(5) 1.180(3) 0.086(15) Uiso 1 1 d . . . C11 C -0.4728(6) 0.1160(4) 1.2047(2) 0.0633(10) Uani 1 1 d . . . H11 H -0.440(7) 0.103(5) 1.248(3) 0.083(14) Uiso 1 1 d . . . C12 C -0.6005(5) 0.1915(4) 1.18185(19) 0.0596(9) Uani 1 1 d . . . H12 H -0.676(7) 0.235(5) 1.207(3) 0.087(16) Uiso 1 1 d . . . C13 C -0.6365(5) 0.2048(3) 1.11829(17) 0.0527(8) Uani 1 1 d . . . H13 H -0.722(4) 0.257(3) 1.1014(16) 0.031(7) Uiso 1 1 d . . . C14 C -0.6308(5) 0.1222(4) 0.71276(17) 0.0556(8) Uani 1 1 d . . . H14 H -0.620(5) 0.198(4) 0.6990(18) 0.047(9) Uiso 1 1 d . . . H14A H -0.758(6) 0.102(4) 0.696(2) 0.061(11) Uiso 1 1 d . . . C15 C -0.4723(5) 0.0508(3) 0.69564(15) 0.0528(8) Uani 1 1 d . . . H15 H -0.354(5) 0.091(4) 0.7183(19) 0.056(10) Uiso 1 1 d . . . C16 C -0.4931(7) -0.0705(4) 0.71101(19) 0.0677(10) Uani 1 1 d . . . H16 H -0.467(6) -0.087(5) 0.757(3) 0.077(13) Uiso 1 1 d . . . C17 C -0.6733(8) -0.1137(4) 0.6772(2) 0.0798(13) Uani 1 1 d . . . H17 H -0.812(7) -0.126(5) 0.693(3) 0.090(15) Uiso 1 1 d . . . C18 C -0.6268(8) -0.1205(4) 0.6193(2) 0.0792(13) Uani 1 1 d . . . C19 C -0.4264(7) -0.0794(4) 0.61702(19) 0.0686(11) Uani 1 1 d . . . H19 H -0.337(6) -0.097(4) 0.585(3) 0.076(13) Uiso 1 1 d . . . C20 C -0.4419(5) 0.0440(3) 0.62527(16) 0.0533(8) Uani 1 1 d . . . H20 H -0.548(6) 0.077(4) 0.598(2) 0.070(12) Uiso 1 1 d . . . C21 C -0.2700(6) 0.1030(5) 0.6076(2) 0.0708(12) Uani 1 1 d . . . C22 C -0.2160(4) 0.3467(3) 0.80121(16) 0.0521(7) Uani 1 1 d . . . C23 C -0.1669(4) 0.3621(3) 0.86877(15) 0.0458(7) Uani 1 1 d . . . C24 C -0.1027(4) 0.4606(3) 0.89286(17) 0.0483(7) Uani 1 1 d . . . H24 H -0.088(7) 0.522(5) 0.869(3) 0.088(16) Uiso 1 1 d . . . C25 C -0.0621(4) 0.4713(3) 0.95608(17) 0.0486(7) Uani 1 1 d . . . H25 H -0.030(6) 0.546(5) 0.971(2) 0.075(13) Uiso 1 1 d . . . C26 C -0.0816(3) 0.3854(3) 0.99697(15) 0.0433(7) Uani 1 1 d . . . C27 C -0.1438(5) 0.2877(3) 0.97159(18) 0.0520(8) Uani 1 1 d . . . H27 H -0.154(7) 0.223(5) 0.999(3) 0.086(15) Uiso 1 1 d . . . C28 C -0.1865(5) 0.2769(3) 0.90872(19) 0.0563(9) Uani 1 1 d . . . H28 H -0.233(5) 0.217(4) 0.8942(18) 0.046(9) Uiso 1 1 d . . . C29 C -0.0416(4) 0.3979(3) 1.06480(16) 0.0462(7) Uani 1 1 d . . . C30 C 0.0859(5) 0.4746(3) 1.08960(19) 0.0571(9) Uani 1 1 d . . . H30 H 0.158(6) 0.524(4) 1.062(2) 0.065(12) Uiso 1 1 d . . . C31 C 0.1205(6) 0.4861(4) 1.1528(2) 0.0700(11) Uani 1 1 d . . . H31 H 0.200(7) 0.542(5) 1.166(3) 0.091(16) Uiso 1 1 d . . . C32 C 0.0323(6) 0.4214(5) 1.1935(2) 0.0712(12) Uani 1 1 d . . . H32 H 0.048(5) 0.430(4) 1.239(2) 0.070(12) Uiso 1 1 d . . . C33 C -0.0948(5) 0.3450(5) 1.17017(18) 0.0668(10) Uani 1 1 d . . . C34 C -0.1315(4) 0.3344(4) 1.10662(17) 0.0564(8) Uani 1 1 d . . . H34 H -0.236(7) 0.274(6) 1.090(3) 0.099(17) Uiso 1 1 d . . . C35 C -0.2309(6) 0.4275(4) 0.70211(18) 0.0608(9) Uani 1 1 d . . . H35 H -0.359(6) 0.418(4) 0.692(2) 0.074(13) Uiso 1 1 d . . . H35A H -0.177(7) 0.356(6) 0.680(3) 0.096(16) Uiso 1 1 d . . . C36 C -0.1554(5) 0.5287(3) 0.67465(16) 0.0511(8) Uani 1 1 d . . . H36 H -0.233(5) 0.597(4) 0.686(2) 0.058(10) Uiso 1 1 d . . . C37 C 0.0581(5) 0.5508(4) 0.69410(18) 0.0585(9) Uani 1 1 d . . . H37 H 0.082(7) 0.579(5) 0.733(3) 0.093(16) Uiso 1 1 d . . . C38 C 0.1678(5) 0.4527(4) 0.6805(2) 0.0636(10) Uani 1 1 d . . . H38 H 0.214(7) 0.393(5) 0.703(3) 0.091(16) Uiso 1 1 d . . . C39 C 0.1696(5) 0.4522(4) 0.6190(2) 0.0636(10) Uani 1 1 d . . . C40 C 0.0629(5) 0.5510(4) 0.59654(18) 0.0580(8) Uani 1 1 d . . . H40 H 0.110(6) 0.582(5) 0.553(3) 0.079(13) Uiso 1 1 d . . . C41 C -0.1498(5) 0.5249(3) 0.60327(17) 0.0533(8) Uani 1 1 d . . . H41 H -0.190(4) 0.448(3) 0.5852(17) 0.041(8) Uiso 1 1 d . . . C42 C -0.2834(7) 0.6043(4) 0.5707(2) 0.0717(12) Uani 1 1 d . . . H33 H -0.175(6) 0.281(4) 1.197(2) 0.078(13) Uiso 1 1 d . . . Br1 Br 0.24804(10) 0.34433(5) 0.56674(3) 0.1054(2) Uani 1 1 d . . . Br2 Br -0.77985(12) -0.15857(5) 0.54829(2) 0.1210(3) Uani 1 1 d . . . F1 F -0.2428(5) 0.0905(4) 0.54740(15) 0.0995(10) Uani 1 1 d . . . F2 F -0.1104(4) 0.0710(5) 0.63874(18) 0.1223(14) Uani 1 1 d . . . F3 F -0.2828(5) 0.2085(3) 0.61608(17) 0.1046(10) Uani 1 1 d . . . F4 F -0.2695(6) 0.6014(3) 0.50914(14) 0.1071(11) Uani 1 1 d . . . F5 F -0.2455(5) 0.7052(3) 0.58585(16) 0.1019(10) Uani 1 1 d . . . F6 F -0.4605(4) 0.5878(4) 0.5811(2) 0.1331(16) Uani 1 1 d . . . O1 O -0.6352(4) 0.1100(2) 0.77937(12) 0.0557(6) Uani 1 1 d . . . O2 O -0.7629(5) 0.2736(3) 0.78868(14) 0.0847(10) Uani 1 1 d . . . O3 O -0.3443(5) -0.1135(3) 0.67581(14) 0.0829(10) Uani 1 1 d . . . O4 O -0.1856(3) 0.4347(2) 0.76833(11) 0.0559(6) Uani 1 1 d . . . O5 O -0.2804(5) 0.2651(3) 0.77877(15) 0.0839(10) Uani 1 1 d . . . O6 O 0.1042(4) 0.6231(2) 0.64658(14) 0.0666(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0595(17) 0.050(2) 0.0479(19) 0.0012(16) 0.0083(14) 0.0069(15) C2 0.0462(14) 0.0461(18) 0.0426(17) 0.0010(14) 0.0055(12) 0.0028(12) C3 0.0578(15) 0.0411(17) 0.050(2) 0.0017(15) 0.0073(13) -0.0014(15) C4 0.0563(15) 0.0407(18) 0.0452(18) 0.0028(14) 0.0072(13) 0.0030(13) C5 0.0415(12) 0.0427(17) 0.0452(17) 0.0009(13) 0.0048(11) -0.0044(11) C6 0.0626(17) 0.048(2) 0.0430(18) -0.0016(15) 0.0023(14) 0.0106(15) C7 0.0648(18) 0.0468(19) 0.051(2) 0.0032(16) 0.0063(15) 0.0149(15) C8 0.0438(13) 0.0428(17) 0.0452(17) 0.0032(13) 0.0036(12) -0.0028(12) C9 0.0577(16) 0.059(2) 0.048(2) -0.0030(17) -0.0021(14) 0.0111(16) C10 0.0675(18) 0.073(3) 0.050(2) 0.006(2) -0.0074(16) 0.0128(19) C11 0.068(2) 0.076(3) 0.044(2) 0.0054(19) -0.0055(16) -0.0038(18) C12 0.0650(18) 0.064(2) 0.050(2) -0.0064(18) 0.0028(16) -0.0029(17) C13 0.0578(16) 0.051(2) 0.049(2) -0.0006(17) 0.0035(14) 0.0034(15) C14 0.069(2) 0.061(2) 0.0370(17) 0.0006(16) 0.0008(15) 0.0077(17) C15 0.0662(17) 0.057(2) 0.0341(16) -0.0065(15) -0.0053(13) 0.0059(16) C16 0.106(3) 0.058(2) 0.0377(19) 0.0018(17) -0.0042(19) 0.012(2) C17 0.127(4) 0.058(2) 0.054(2) 0.008(2) 0.003(2) -0.019(3) C18 0.140(4) 0.047(2) 0.048(2) 0.0035(18) -0.009(2) -0.018(2) C19 0.109(3) 0.056(2) 0.041(2) -0.0061(17) 0.006(2) 0.013(2) C20 0.0689(18) 0.056(2) 0.0345(16) -0.0072(15) 0.0006(14) 0.0024(16) C21 0.082(2) 0.083(3) 0.046(2) -0.009(2) 0.0029(18) -0.004(2) C22 0.0544(14) 0.0520(19) 0.0501(17) 0.0020(18) 0.0055(13) -0.0101(15) C23 0.0466(13) 0.0465(19) 0.0444(16) 0.0020(14) 0.0049(11) -0.0004(12) C24 0.0538(15) 0.0438(18) 0.0482(19) 0.0023(15) 0.0094(13) -0.0008(13) C25 0.0538(15) 0.0431(19) 0.050(2) -0.0020(15) 0.0091(13) -0.0023(13) C26 0.0343(11) 0.0478(17) 0.0479(17) 0.0010(14) 0.0028(11) 0.0023(11) C27 0.0578(16) 0.047(2) 0.050(2) 0.0037(15) -0.0007(14) -0.0067(14) C28 0.0642(18) 0.049(2) 0.055(2) 0.0037(17) 0.0005(16) -0.0153(16) C29 0.0433(13) 0.0485(18) 0.0470(18) 0.0010(14) 0.0056(12) 0.0028(12) C30 0.0617(18) 0.057(2) 0.053(2) -0.0004(17) 0.0020(15) -0.0111(16) C31 0.073(2) 0.080(3) 0.055(2) -0.003(2) -0.0060(18) -0.017(2) C32 0.078(2) 0.089(3) 0.047(2) 0.000(2) 0.0019(18) -0.002(2) C33 0.0729(19) 0.079(3) 0.0492(19) 0.008(2) 0.0115(16) -0.012(2) C34 0.0556(15) 0.063(2) 0.0518(18) 0.0003(19) 0.0088(13) -0.0086(17) C35 0.076(2) 0.067(3) 0.0397(18) -0.0001(17) 0.0014(16) -0.0170(19) C36 0.0655(17) 0.054(2) 0.0333(16) -0.0063(14) 0.0013(13) -0.0003(15) C37 0.0721(19) 0.064(2) 0.0383(18) 0.0001(18) -0.0014(15) -0.0126(18) C38 0.0666(19) 0.069(3) 0.054(2) 0.014(2) -0.0034(16) 0.0013(19) C39 0.0648(18) 0.072(3) 0.055(2) 0.010(2) 0.0081(16) 0.0125(18) C40 0.0742(19) 0.057(2) 0.0432(19) 0.0060(17) 0.0085(15) 0.0043(17) C41 0.0699(19) 0.051(2) 0.0380(17) 0.0045(15) -0.0030(14) 0.0059(15) C42 0.093(3) 0.071(3) 0.050(3) 0.002(2) -0.0063(19) 0.019(2) Br1 0.1395(4) 0.1034(4) 0.0760(3) 0.0037(3) 0.0259(3) 0.0579(4) Br2 0.2077(7) 0.0895(4) 0.0595(3) 0.0109(3) -0.0331(3) -0.0701(5) F1 0.122(2) 0.125(3) 0.0556(18) -0.0124(18) 0.0327(15) -0.027(2) F2 0.0679(13) 0.191(4) 0.107(3) 0.005(3) 0.0006(14) 0.000(2) F3 0.135(2) 0.081(2) 0.102(2) -0.0211(19) 0.0328(19) -0.0407(19) F4 0.168(3) 0.099(2) 0.0490(15) 0.0081(16) -0.0245(16) 0.041(2) F5 0.147(2) 0.0607(17) 0.094(2) -0.0033(17) -0.0184(19) 0.0342(18) F6 0.0718(16) 0.164(4) 0.160(4) 0.058(3) -0.0142(17) 0.017(2) O1 0.0753(14) 0.0513(16) 0.0414(13) 0.0022(11) 0.0097(11) 0.0057(11) O2 0.126(2) 0.080(2) 0.0479(16) 0.0057(16) 0.0029(16) 0.051(2) O3 0.128(2) 0.074(2) 0.0450(15) -0.0012(15) -0.0028(15) 0.0428(19) O4 0.0727(13) 0.0557(15) 0.0393(13) -0.0011(11) 0.0053(10) -0.0070(12) O5 0.123(2) 0.072(2) 0.0541(17) -0.0009(16) -0.0109(16) -0.0402(19) O6 0.0809(15) 0.0608(17) 0.0580(17) 0.0049(14) 0.0045(13) -0.0136(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.203(5) . ? C1 O1 1.328(5) . ? C1 C2 1.488(5) . ? C2 C7 1.382(5) . ? C2 C3 1.382(5) . ? C3 C4 1.383(5) . ? C4 C5 1.394(5) . ? C5 C6 1.396(5) . ? C5 C8 1.476(5) . ? C6 C7 1.377(5) . ? C8 C13 1.390(5) . ? C8 C9 1.393(5) . ? C9 C10 1.375(6) . ? C10 C11 1.381(6) . ? C11 C12 1.368(6) . ? C12 C13 1.387(6) . ? C14 O1 1.449(4) . ? C14 C15 1.496(5) . ? C15 C20 1.553(5) . ? C15 C16 1.555(6) . ? C16 O3 1.444(6) . ? C16 C17 1.517(7) . ? C17 C18 1.319(7) . ? C18 C19 1.509(7) . ? C18 Br2 1.869(4) . ? C19 O3 1.421(5) . ? C19 C20 1.551(6) . ? C20 C21 1.491(6) . ? C21 F3 1.329(7) . ? C21 F2 1.330(6) . ? C21 F1 1.338(5) . ? C22 O5 1.200(5) . ? C22 O4 1.331(5) . ? C22 C23 1.487(5) . ? C23 C28 1.380(5) . ? C23 C24 1.394(5) . ? C24 C25 1.380(5) . ? C25 C26 1.400(5) . ? C26 C27 1.392(5) . ? C26 C29 1.479(5) . ? C27 C28 1.375(6) . ? C29 C34 1.389(5) . ? C29 C30 1.391(5) . ? C30 C31 1.376(6) . ? C31 C32 1.375(7) . ? C32 C33 1.377(7) . ? C33 C34 1.384(5) . ? C35 O4 1.445(5) . ? C35 C36 1.507(6) . ? C36 C41 1.546(5) . ? C36 C37 1.559(5) . ? C37 O6 1.421(5) . ? C37 C38 1.486(7) . ? C38 C39 1.329(6) . ? C39 C40 1.504(6) . ? C39 Br1 1.864(5) . ? C40 O6 1.418(5) . ? C40 C41 1.554(6) . ? C41 C42 1.504(6) . ? C42 F6 1.303(6) . ? C42 F5 1.320(7) . ? C42 F4 1.340(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 124.5(4) . . ? O2 C1 C2 123.4(3) . . ? O1 C1 C2 112.1(3) . . ? C7 C2 C3 118.9(3) . . ? C7 C2 C1 118.9(3) . . ? C3 C2 C1 122.1(3) . . ? C2 C3 C4 120.2(3) . . ? C3 C4 C5 121.6(3) . . ? C4 C5 C6 117.1(3) . . ? C4 C5 C8 121.2(3) . . ? C6 C5 C8 121.6(3) . . ? C7 C6 C5 121.3(3) . . ? C6 C7 C2 120.8(3) . . ? C13 C8 C9 117.1(3) . . ? C13 C8 C5 121.8(3) . . ? C9 C8 C5 121.0(3) . . ? C10 C9 C8 121.8(4) . . ? C9 C10 C11 119.9(4) . . ? C12 C11 C10 119.6(4) . . ? C11 C12 C13 120.4(4) . . ? C12 C13 C8 121.1(3) . . ? O1 C14 C15 104.8(3) . . ? C14 C15 C20 115.8(3) . . ? C14 C15 C16 116.0(3) . . ? C20 C15 C16 100.3(3) . . ? O3 C16 C17 103.4(4) . . ? O3 C16 C15 99.4(3) . . ? C17 C16 C15 109.3(3) . . ? C18 C17 C16 102.7(5) . . ? C17 C18 C19 108.0(4) . . ? C17 C18 Br2 128.6(4) . . ? C19 C18 Br2 123.1(3) . . ? O3 C19 C18 101.0(4) . . ? O3 C19 C20 102.8(3) . . ? C18 C19 C20 105.0(4) . . ? C21 C20 C19 113.1(4) . . ? C21 C20 C15 113.4(3) . . ? C19 C20 C15 100.5(3) . . ? F3 C21 F2 106.9(5) . . ? F3 C21 F1 105.3(4) . . ? F2 C21 F1 106.2(4) . . ? F3 C21 C20 112.7(4) . . ? F2 C21 C20 113.5(4) . . ? F1 C21 C20 111.7(4) . . ? O5 C22 O4 123.5(3) . . ? O5 C22 C23 124.0(3) . . ? O4 C22 C23 112.5(3) . . ? C28 C23 C24 119.2(3) . . ? C28 C23 C22 119.2(3) . . ? C24 C23 C22 121.7(3) . . ? C25 C24 C23 119.5(3) . . ? C24 C25 C26 121.8(3) . . ? C27 C26 C25 117.5(3) . . ? C27 C26 C29 120.9(3) . . ? C25 C26 C29 121.6(3) . . ? C28 C27 C26 120.9(3) . . ? C27 C28 C23 121.1(4) . . ? C34 C29 C30 117.0(3) . . ? C34 C29 C26 121.4(3) . . ? C30 C29 C26 121.6(3) . . ? C31 C30 C29 121.1(4) . . ? C32 C31 C30 121.1(4) . . ? C31 C32 C33 119.0(4) . . ? C32 C33 C34 119.8(4) . . ? C33 C34 C29 122.0(4) . . ? O4 C35 C36 106.2(3) . . ? C35 C36 C41 113.7(3) . . ? C35 C36 C37 113.9(3) . . ? C41 C36 C37 100.3(3) . . ? O6 C37 C38 103.1(3) . . ? O6 C37 C36 100.7(3) . . ? C38 C37 C36 108.1(3) . . ? C39 C38 C37 104.2(4) . . ? C38 C39 C40 106.1(4) . . ? C38 C39 Br1 129.3(4) . . ? C40 C39 Br1 123.9(3) . . ? O6 C40 C39 101.6(3) . . ? O6 C40 C41 101.9(3) . . ? C39 C40 C41 105.3(3) . . ? C42 C41 C36 112.6(3) . . ? C42 C41 C40 113.3(3) . . ? C36 C41 C40 100.6(3) . . ? F6 C42 F5 106.7(5) . . ? F6 C42 F4 108.0(4) . . ? F5 C42 F4 104.1(4) . . ? F6 C42 C41 113.1(4) . . ? F5 C42 C41 113.6(4) . . ? F4 C42 C41 110.9(4) . . ? C1 O1 C14 117.8(3) . . ? C19 O3 C16 95.4(3) . . ? C22 O4 C35 116.4(3) . . ? C40 O6 C37 96.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C7 -8.9(6) . . . . ? O1 C1 C2 C7 170.4(3) . . . . ? O2 C1 C2 C3 173.0(4) . . . . ? O1 C1 C2 C3 -7.7(4) . . . . ? C7 C2 C3 C4 0.7(5) . . . . ? C1 C2 C3 C4 178.8(3) . . . . ? C2 C3 C4 C5 -2.4(5) . . . . ? C3 C4 C5 C6 2.4(4) . . . . ? C3 C4 C5 C8 -179.4(3) . . . . ? C4 C5 C6 C7 -0.9(5) . . . . ? C8 C5 C6 C7 -179.0(3) . . . . ? C5 C6 C7 C2 -0.7(5) . . . . ? C3 C2 C7 C6 0.8(5) . . . . ? C1 C2 C7 C6 -177.4(3) . . . . ? C4 C5 C8 C13 -150.8(3) . . . . ? C6 C5 C8 C13 27.2(5) . . . . ? C4 C5 C8 C9 28.3(4) . . . . ? C6 C5 C8 C9 -153.6(3) . . . . ? C13 C8 C9 C10 0.4(5) . . . . ? C5 C8 C9 C10 -178.8(4) . . . . ? C8 C9 C10 C11 -0.6(6) . . . . ? C9 C10 C11 C12 0.3(7) . . . . ? C10 C11 C12 C13 0.2(6) . . . . ? C11 C12 C13 C8 -0.4(6) . . . . ? C9 C8 C13 C12 0.1(5) . . . . ? C5 C8 C13 C12 179.3(3) . . . . ? O1 C14 C15 C20 177.1(3) . . . . ? O1 C14 C15 C16 60.0(4) . . . . ? C14 C15 C16 O3 167.3(3) . . . . ? C20 C15 C16 O3 41.8(3) . . . . ? C14 C15 C16 C17 59.4(4) . . . . ? C20 C15 C16 C17 -66.0(4) . . . . ? O3 C16 C17 C18 -30.7(5) . . . . ? C15 C16 C17 C18 74.5(5) . . . . ? C16 C17 C18 C19 -1.8(5) . . . . ? C16 C17 C18 Br2 -175.4(4) . . . . ? C17 C18 C19 O3 34.1(5) . . . . ? Br2 C18 C19 O3 -151.9(3) . . . . ? C17 C18 C19 C20 -72.4(5) . . . . ? Br2 C18 C19 C20 101.6(4) . . . . ? O3 C19 C20 C21 90.2(4) . . . . ? C18 C19 C20 C21 -164.5(3) . . . . ? O3 C19 C20 C15 -31.1(4) . . . . ? C18 C19 C20 C15 74.2(4) . . . . ? C14 C15 C20 C21 106.6(4) . . . . ? C16 C15 C20 C21 -127.8(4) . . . . ? C14 C15 C20 C19 -132.4(4) . . . . ? C16 C15 C20 C19 -6.7(4) . . . . ? C19 C20 C21 F3 -178.7(4) . . . . ? C15 C20 C21 F3 -65.0(5) . . . . ? C19 C20 C21 F2 -57.0(5) . . . . ? C15 C20 C21 F2 56.7(5) . . . . ? C19 C20 C21 F1 63.0(5) . . . . ? C15 C20 C21 F1 176.6(4) . . . . ? O5 C22 C23 C28 3.3(5) . . . . ? O4 C22 C23 C28 -178.4(3) . . . . ? O5 C22 C23 C24 -176.2(4) . . . . ? O4 C22 C23 C24 2.0(4) . . . . ? C28 C23 C24 C25 -0.7(5) . . . . ? C22 C23 C24 C25 178.9(3) . . . . ? C23 C24 C25 C26 0.7(5) . . . . ? C24 C25 C26 C27 0.1(4) . . . . ? C24 C25 C26 C29 -178.7(3) . . . . ? C25 C26 C27 C28 -0.8(5) . . . . ? C29 C26 C27 C28 178.0(3) . . . . ? C26 C27 C28 C23 0.8(5) . . . . ? C24 C23 C28 C27 -0.1(5) . . . . ? C22 C23 C28 C27 -179.6(3) . . . . ? C27 C26 C29 C34 -26.6(4) . . . . ? C25 C26 C29 C34 152.2(3) . . . . ? C27 C26 C29 C30 154.2(3) . . . . ? C25 C26 C29 C30 -27.0(4) . . . . ? C34 C29 C30 C31 0.1(6) . . . . ? C26 C29 C30 C31 179.3(4) . . . . ? C29 C30 C31 C32 0.9(7) . . . . ? C30 C31 C32 C33 -1.0(8) . . . . ? C31 C32 C33 C34 0.0(7) . . . . ? C32 C33 C34 C29 1.0(7) . . . . ? C30 C29 C34 C33 -1.1(6) . . . . ? C26 C29 C34 C33 179.7(4) . . . . ? O4 C35 C36 C41 167.0(3) . . . . ? O4 C35 C36 C37 53.0(4) . . . . ? C35 C36 C37 O6 160.2(3) . . . . ? C41 C36 C37 O6 38.4(4) . . . . ? C35 C36 C37 C38 52.5(4) . . . . ? C41 C36 C37 C38 -69.4(4) . . . . ? O6 C37 C38 C39 -32.8(4) . . . . ? C36 C37 C38 C39 73.3(4) . . . . ? C37 C38 C39 C40 0.7(4) . . . . ? C37 C38 C39 Br1 -169.8(3) . . . . ? C38 C39 C40 O6 31.4(4) . . . . ? Br1 C39 C40 O6 -157.5(3) . . . . ? C38 C39 C40 C41 -74.6(4) . . . . ? Br1 C39 C40 C41 96.6(3) . . . . ? C35 C36 C41 C42 114.5(4) . . . . ? C37 C36 C41 C42 -123.6(4) . . . . ? C35 C36 C41 C40 -124.6(4) . . . . ? C37 C36 C41 C40 -2.7(4) . . . . ? O6 C40 C41 C42 86.5(4) . . . . ? C39 C40 C41 C42 -167.7(4) . . . . ? O6 C40 C41 C36 -33.9(4) . . . . ? C39 C40 C41 C36 71.8(4) . . . . ? C36 C41 C42 F6 -60.8(6) . . . . ? C40 C41 C42 F6 -174.1(4) . . . . ? C36 C41 C42 F5 60.9(5) . . . . ? C40 C41 C42 F5 -52.4(5) . . . . ? C36 C41 C42 F4 177.7(4) . . . . ? C40 C41 C42 F4 64.4(5) . . . . ? O2 C1 O1 C14 9.5(6) . . . . ? C2 C1 O1 C14 -169.8(3) . . . . ? C15 C14 O1 C1 149.5(3) . . . . ? C18 C19 O3 C16 -49.9(4) . . . . ? C20 C19 O3 C16 58.4(4) . . . . ? C17 C16 O3 C19 50.3(4) . . . . ? C15 C16 O3 C19 -62.2(4) . . . . ? O5 C22 O4 C35 -1.3(6) . . . . ? C23 C22 O4 C35 -179.5(3) . . . . ? C36 C35 O4 C22 -171.0(3) . . . . ? C39 C40 O6 C37 -49.2(3) . . . . ? C41 C40 O6 C37 59.3(3) . . . . ? C38 C37 O6 C40 50.8(3) . . . . ? C36 C37 O6 C40 -60.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.389 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.046 _publ_section_references ;Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. ; _chemical_absolute_configuration ad