# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dieter Lentz' _publ_contact_author_address ; Institut f\"ur Chemie - Anorganische und Analytische Chemie Freie Universit\"at Berlin Fabeckstrasse 34-36 Berlin Berlin D-14195 GERMANY ; _publ_contact_author_email LENTZ@CHEMIE.FU-BERLIN.DE _publ_section_title ; Diels-Alder Reactions of 1,1,4,4-Tetrafluorobutatriene ; loop_ _publ_author_name 'Dieter Lentz' 'Christian Ehm' # Attachment 'ce283n_final.cif' data_ce283n _database_code_depnum_ccdc_archive 'CCDC 752618' #TrackingRef 'ce283n_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;1,1,3,3-tetrafluoro-4,9-diphenyl-1,3-dihydronaphtho(2,3- c)furan ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H14 F4 O' _chemical_formula_weight 394.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 14.189(5) _cell_length_b 7.746(3) _cell_length_c 16.523(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1816.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 903 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.3 _exptl_crystal_description platelett _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26842 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 30.58 _reflns_number_total 2857 _reflns_number_gt 2601 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART BRUKER-AXS' _computing_cell_refinement 'SAINT BRUKER-aXS)' _computing_data_reduction 'SAINT BRUKER-aXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia)' _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^)+(0.0946P)^2^+0.2675P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(7) _refine_ls_number_reflns 2857 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.67864(15) 1.1170(3) 0.09190(15) 0.0235(4) Uani 1 1 d . . . C2 C 0.65561(14) 1.0285(3) 0.17008(13) 0.0187(4) Uani 1 1 d . . . C3 C 0.69691(13) 0.8868(3) 0.20493(13) 0.0184(4) Uani 1 1 d . . . C4 C 0.65991(14) 0.8327(3) 0.28137(13) 0.0180(4) Uani 1 1 d . . . C5 C 0.69858(16) 0.6880(3) 0.32216(14) 0.0220(4) Uani 1 1 d . . . H5 H 0.7503 0.6282 0.2988 0.026 Uiso 1 1 calc R . . C6 C 0.66267(17) 0.6331(3) 0.39453(15) 0.0253(5) Uani 1 1 d . . . H6 H 0.6903 0.5371 0.4213 0.030 Uiso 1 1 calc R . . C7 C 0.58473(18) 0.7185(3) 0.42968(14) 0.0261(5) Uani 1 1 d . . . H7 H 0.5592 0.6781 0.4794 0.031 Uiso 1 1 calc R . . C8 C 0.54584(16) 0.8594(3) 0.39217(13) 0.0225(4) Uani 1 1 d . . . H8 H 0.4934 0.9158 0.4162 0.027 Uiso 1 1 calc R . . C9 C 0.58261(13) 0.9224(3) 0.31818(12) 0.0170(4) Uani 1 1 d . . . C10 C 0.54356(13) 1.0728(3) 0.27994(12) 0.0170(4) Uani 1 1 d . . . C11 C 0.58210(13) 1.1200(3) 0.20709(13) 0.0185(4) Uani 1 1 d . . . C12 C 0.56197(16) 1.2749(3) 0.15640(15) 0.0237(4) Uani 1 1 d . . . C13 C 0.77707(14) 0.7947(3) 0.16526(13) 0.0186(4) Uani 1 1 d . . . C14 C 0.75969(16) 0.6670(4) 0.10824(16) 0.0287(5) Uani 1 1 d . . . H14 H 0.6966 0.6370 0.0952 0.034 Uiso 1 1 calc R . . C15 C 0.83380(18) 0.5827(4) 0.07019(16) 0.0306(5) Uani 1 1 d . . . H15 H 0.8215 0.4934 0.0322 0.037 Uiso 1 1 calc R . . C16 C 0.92645(16) 0.6297(4) 0.08796(16) 0.0271(5) Uani 1 1 d . . . H16 H 0.9773 0.5762 0.0603 0.032 Uiso 1 1 calc R . . C17 C 0.94410(16) 0.7540(4) 0.14573(19) 0.0299(5) Uani 1 1 d . . . H17 H 1.0073 0.7828 0.1591 0.036 Uiso 1 1 calc R . . C18 C 0.86971(15) 0.8378(3) 0.18466(18) 0.0280(5) Uani 1 1 d . . . H18 H 0.8822 0.9238 0.2242 0.034 Uiso 1 1 calc R . . C19 C 0.48174(17) 1.2758(4) 0.38507(16) 0.0284(5) Uani 1 1 d . . . H19 H 0.5432 1.2818 0.4077 0.034 Uiso 1 1 calc R . . C20 C 0.4082(2) 1.3704(4) 0.41945(19) 0.0352(6) Uani 1 1 d . . . H20 H 0.4196 1.4420 0.4651 0.042 Uiso 1 1 calc R . . C21 C 0.31812(19) 1.3595(4) 0.38656(18) 0.0346(6) Uani 1 1 d . . . H21 H 0.2680 1.4239 0.4099 0.042 Uiso 1 1 calc R . . C22 C 0.30119(17) 1.2559(4) 0.32053(17) 0.0304(5) Uani 1 1 d . . . H22 H 0.2393 1.2479 0.2990 0.036 Uiso 1 1 calc R . . C23 C 0.37455(14) 1.1626(3) 0.28503(14) 0.0229(4) Uani 1 1 d . . . H23 H 0.3629 1.0925 0.2389 0.027 Uiso 1 1 calc R . . C24 C 0.46496(14) 1.1728(3) 0.31768(13) 0.0185(4) Uani 1 1 d . . . F1 F 0.66223(11) 1.0197(2) 0.02569(9) 0.0309(3) Uani 1 1 d . . . F2 F 0.76859(10) 1.1699(2) 0.08587(10) 0.0304(3) Uani 1 1 d . . . F3 F 0.58132(12) 1.4248(2) 0.19482(11) 0.0333(3) Uani 1 1 d . . . F4 F 0.47286(11) 1.2907(2) 0.12990(9) 0.0305(4) Uani 1 1 d . . . O1 O 0.62018(13) 1.2623(3) 0.08783(12) 0.0321(4) 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 0.0164(8) 0.0290(11) 0.0252(10) 0.0030(9) 0.0040(8) -0.0004(8) C2 0.0135(7) 0.0247(10) 0.0181(8) 0.0010(7) 0.0013(6) -0.0017(7) C3 0.0119(7) 0.0231(10) 0.0201(9) -0.0027(7) 0.0009(7) -0.0012(7) C4 0.0119(8) 0.0235(10) 0.0186(8) -0.0016(8) -0.0016(7) -0.0011(7) C5 0.0189(9) 0.0239(10) 0.0233(10) -0.0011(8) -0.0022(8) 0.0016(8) C6 0.0270(10) 0.0258(12) 0.0229(10) 0.0008(9) -0.0041(8) 0.0024(9) C7 0.0288(11) 0.0313(13) 0.0181(9) 0.0003(9) 0.0009(8) -0.0011(9) C8 0.0202(9) 0.0288(12) 0.0185(9) -0.0027(8) 0.0023(7) -0.0021(8) C9 0.0118(7) 0.0221(10) 0.0171(8) -0.0017(7) -0.0009(6) -0.0009(7) C10 0.0113(7) 0.0215(10) 0.0180(8) -0.0021(7) -0.0006(6) -0.0003(7) C11 0.0119(7) 0.0227(10) 0.0207(9) -0.0003(7) -0.0002(7) 0.0015(7) C12 0.0171(9) 0.0282(12) 0.0257(10) 0.0044(9) 0.0008(8) 0.0027(8) C13 0.0143(8) 0.0208(10) 0.0208(9) -0.0004(7) 0.0018(7) 0.0020(7) C14 0.0168(9) 0.0380(14) 0.0314(11) -0.0108(10) -0.0024(8) 0.0037(9) C15 0.0263(10) 0.0371(15) 0.0286(12) -0.0083(10) -0.0016(9) 0.0092(10) C16 0.0208(9) 0.0326(13) 0.0278(10) 0.0026(10) 0.0055(8) 0.0098(9) C17 0.0115(8) 0.0298(13) 0.0484(15) -0.0036(11) 0.0048(9) 0.0017(8) C18 0.0138(8) 0.0277(12) 0.0426(13) -0.0101(10) 0.0010(8) 0.0008(8) C19 0.0195(10) 0.0347(14) 0.0308(12) -0.0107(10) 0.0029(8) -0.0007(9) C20 0.0352(13) 0.0348(14) 0.0357(13) -0.0117(11) 0.0094(11) 0.0027(11) C21 0.0286(12) 0.0396(15) 0.0357(14) 0.0036(11) 0.0128(10) 0.0143(11) C22 0.0169(9) 0.0416(14) 0.0325(12) 0.0101(11) 0.0054(9) 0.0105(9) C23 0.0132(8) 0.0322(12) 0.0233(9) 0.0020(9) 0.0009(7) 0.0017(8) C24 0.0140(8) 0.0212(10) 0.0204(9) -0.0005(7) 0.0029(7) 0.0008(7) F1 0.0284(7) 0.0429(9) 0.0215(7) 0.0005(6) 0.0023(6) -0.0016(6) F2 0.0177(6) 0.0372(8) 0.0362(8) 0.0050(7) 0.0084(6) -0.0047(5) F3 0.0329(7) 0.0288(8) 0.0383(8) 0.0008(7) -0.0017(7) 0.0017(6) F4 0.0196(6) 0.0445(10) 0.0276(7) 0.0068(6) -0.0032(5) 0.0082(6) O1 0.0274(9) 0.0354(10) 0.0334(10) 0.0114(8) 0.0080(8) 0.0079(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F2 1.344(2) . ? C1 F1 1.349(3) . ? C1 O1 1.399(3) . ? C1 C2 1.499(3) . ? C2 C3 1.371(3) . ? C2 C11 1.402(3) . ? C3 C4 1.431(3) . ? C3 C13 1.494(3) . ? C4 C5 1.418(3) . ? C4 C9 1.434(3) . ? C5 C6 1.368(3) . ? C5 H5 0.9500 . ? C6 C7 1.413(3) . ? C6 H6 0.9500 . ? C7 C8 1.371(4) . ? C7 H7 0.9500 . ? C8 C9 1.416(3) . ? C8 H8 0.9500 . ? C9 C10 1.437(3) . ? C10 C11 1.372(3) . ? C10 C24 1.494(3) . ? C11 C12 1.491(3) . ? C12 F4 1.344(3) . ? C12 F3 1.352(3) . ? C12 O1 1.405(3) . ? C13 C14 1.388(3) . ? C13 C18 1.394(3) . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 C16 1.395(4) . ? C15 H15 0.9500 . ? C16 C17 1.379(4) . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.391(3) . ? C19 C20 1.395(4) . ? C19 H19 0.9500 . ? C20 C21 1.392(4) . ? C20 H20 0.9500 . ? C21 C22 1.375(4) . ? C21 H21 0.9500 . ? C22 C23 1.397(3) . ? C22 H22 0.9500 . ? C23 C24 1.394(3) . ? C23 H23 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 F2 C1 F1 105.91(18) . . ? F2 C1 O1 108.3(2) . . ? F1 C1 O1 107.9(2) . . ? F2 C1 C2 114.23(19) . . ? F1 C1 C2 113.9(2) . . ? O1 C1 C2 106.27(18) . . ? C3 C2 C11 122.67(19) . . ? C3 C2 C1 129.44(19) . . ? C11 C2 C1 107.86(19) . . ? C2 C3 C4 116.65(18) . . ? C2 C3 C13 121.57(19) . . ? C4 C3 C13 121.78(19) . . ? C5 C4 C3 120.61(19) . . ? C5 C4 C9 118.5(2) . . ? C3 C4 C9 120.89(19) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.1(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.1(2) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C4 118.8(2) . . ? C8 C9 C10 121.13(19) . . ? C4 C9 C10 120.08(18) . . ? C11 C10 C9 116.64(19) . . ? C11 C10 C24 121.7(2) . . ? C9 C10 C24 121.66(18) . . ? C10 C11 C2 123.0(2) . . ? C10 C11 C12 129.1(2) . . ? C2 C11 C12 107.73(18) . . ? F4 C12 F3 105.4(2) . . ? F4 C12 O1 107.3(2) . . ? F3 C12 O1 108.6(2) . . ? F4 C12 C11 115.9(2) . . ? F3 C12 C11 112.9(2) . . ? O1 C12 C11 106.53(19) . . ? C14 C13 C18 119.6(2) . . ? C14 C13 C3 120.18(19) . . ? C18 C13 C3 120.2(2) . . ? C13 C14 C15 120.5(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 119.7(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.4(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.7(2) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C24 C19 C20 120.0(2) . . ? C24 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C21 C20 C19 119.7(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.4(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 119.6(2) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C19 C24 C23 120.0(2) . . ? C19 C24 C10 120.26(19) . . ? C23 C24 C10 119.7(2) . . ? C1 O1 C12 111.44(19) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.500 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.075 # Attachment 'ce283final.cif' data_ce283 _database_code_depnum_ccdc_archive 'CCDC 752619' #TrackingRef 'ce283final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2,3-bis(difluoromethylene)-1,2,3,4-tetrahydro-1,4-diphenyl- 1,4-epoxynaphthalene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H14 F4 O' _chemical_formula_weight 394.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.810(6) _cell_length_b 8.927(3) _cell_length_c 26.933(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.120(10) _cell_angle_gamma 90.00 _cell_volume 3560(2) _cell_formula_units_Z 8 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 771 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.1 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7455 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER-AXS SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21334 _diffrn_reflns_av_R_equivalents 0.1449 _diffrn_reflns_av_sigmaI/netI 0.1502 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 23.25 _reflns_number_total 5070 _reflns_number_gt 2944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker-AXS)' _computing_cell_refinement 'SAINT (Bruker-AXS)' _computing_data_reduction 'SAINT (Bruker-AXS)' _computing_structure_solution 'SIR 97 (Altomare et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia)' _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. An inspection of the data set revealed that the reflexions -1 0 1 and 0 0 2 have F2 close to zero as they are in the shadow of the primary beam stop. Thus they were omitted from the refinement. ; _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^)+(0.1642P)^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 5070 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1560 _refine_ls_R_factor_gt 0.0971 _refine_ls_wR_factor_ref 0.2684 _refine_ls_wR_factor_gt 0.2189 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.5848(5) 0.1188(8) -0.0267(2) 0.0279(16) Uani 1 1 d . . . C2A C 0.5761(4) 0.2190(7) 0.0093(2) 0.0245(15) Uani 1 1 d . . . C3A C 0.6504(4) 0.2743(7) 0.0442(2) 0.0227(15) Uani 1 1 d . . . C4A C 0.6464(4) 0.1707(7) 0.0893(2) 0.0233(15) Uani 1 1 d . . . C5A C 0.6992(5) 0.0541(8) 0.1063(2) 0.0310(17) Uani 1 1 d . . . H5A H 0.7519 0.0242 0.0894 0.037 Uiso 1 1 calc R . . C6A C 0.6722(5) -0.0187(8) 0.1494(2) 0.0308(17) Uani 1 1 d . . . H6A H 0.7090 -0.0959 0.1632 0.037 Uiso 1 1 calc R . . C7A C 0.5917(5) 0.0202(8) 0.1725(2) 0.0295(16) Uani 1 1 d . . . H7A H 0.5743 -0.0317 0.2016 0.035 Uiso 1 1 calc R . . C8A C 0.5373(4) 0.1333(7) 0.1536(2) 0.0271(16) Uani 1 1 d . . . H8A H 0.4821 0.1586 0.1689 0.033 Uiso 1 1 calc R . . C9A C 0.5652(4) 0.2081(7) 0.1119(2) 0.0272(16) Uani 1 1 d . . . C10A C 0.5255(4) 0.3392(7) 0.0815(2) 0.0244(15) Uani 1 1 d . . . C11A C 0.4912(4) 0.2750(7) 0.0314(2) 0.0231(15) Uani 1 1 d . . . C12A C 0.4119(5) 0.2841(8) 0.0107(2) 0.0273(16) Uani 1 1 d . . . C13A C 0.7420(4) 0.3105(7) 0.0227(2) 0.0231(15) Uani 1 1 d . . . C14A C 0.7501(4) 0.3427(8) -0.0275(2) 0.0290(16) Uani 1 1 d . . . H14A H 0.6980 0.3441 -0.0487 0.035 Uiso 1 1 calc R . . C15A C 0.8346(5) 0.3730(7) -0.0468(2) 0.0287(16) Uani 1 1 d . . . H15A H 0.8395 0.3962 -0.0811 0.034 Uiso 1 1 calc R . . C16A C 0.9110(5) 0.3699(7) -0.0171(2) 0.0280(16) Uani 1 1 d . . . H16A H 0.9687 0.3867 -0.0309 0.034 Uiso 1 1 calc R . . C17A C 0.9035(5) 0.3421(7) 0.0334(3) 0.0299(16) Uani 1 1 d . . . H17A H 0.9557 0.3441 0.0544 0.036 Uiso 1 1 calc R . . C18A C 0.8185(5) 0.3110(7) 0.0532(2) 0.0266(16) Uani 1 1 d . . . H18A H 0.8134 0.2902 0.0876 0.032 Uiso 1 1 calc R . . C19A C 0.4669(4) 0.4473(7) 0.1095(2) 0.0239(15) Uani 1 1 d . . . C20A C 0.4926(5) 0.5958(7) 0.1174(2) 0.0274(16) Uani 1 1 d . . . H20A H 0.5477 0.6321 0.1045 0.033 Uiso 1 1 calc R . . C21A C 0.4371(5) 0.6907(8) 0.1443(2) 0.0330(17) Uani 1 1 d . . . H21A H 0.4549 0.7917 0.1498 0.040 Uiso 1 1 calc R . . C22A C 0.3559(5) 0.6399(8) 0.1633(2) 0.0308(17) Uani 1 1 d . . . H22A H 0.3177 0.7061 0.1808 0.037 Uiso 1 1 calc R . . C23A C 0.3314(5) 0.4903(8) 0.1562(2) 0.0296(16) Uani 1 1 d . . . H23A H 0.2768 0.4539 0.1697 0.036 Uiso 1 1 calc R . . C24A C 0.3859(4) 0.3950(8) 0.1299(2) 0.0291(16) Uani 1 1 d . . . H24A H 0.3687 0.2933 0.1256 0.035 Uiso 1 1 calc R . . C1B C 0.5346(5) 0.3137(8) 0.2815(2) 0.0295(16) Uani 1 1 d . . . C2B C 0.5132(4) 0.1891(7) 0.3057(2) 0.0230(15) Uani 1 1 d . . . C3B C 0.5620(4) 0.1329(7) 0.3534(2) 0.0255(15) Uani 1 1 d . . . C4B C 0.6354(4) 0.0295(7) 0.3343(2) 0.0230(15) Uani 1 1 d . . . C5B C 0.7278(4) 0.0402(8) 0.3306(2) 0.0265(16) Uani 1 1 d . . . H5B H 0.7590 0.1255 0.3432 0.032 Uiso 1 1 calc R . . C6B C 0.7742(5) -0.0747(8) 0.3084(2) 0.0323(17) Uani 1 1 d . . . H6B H 0.8380 -0.0692 0.3062 0.039 Uiso 1 1 calc R . . C7B C 0.7279(5) -0.2000(8) 0.2891(2) 0.0309(17) Uani 1 1 d . . . H7B H 0.7607 -0.2788 0.2741 0.037 Uiso 1 1 calc R . . C8B C 0.6328(4) -0.2092(8) 0.2921(2) 0.0275(16) Uani 1 1 d . . . H8B H 0.6010 -0.2927 0.2786 0.033 Uiso 1 1 calc R . . C9B C 0.5877(4) -0.0947(7) 0.3148(2) 0.0242(15) Uani 1 1 d . . . C10B C 0.4868(4) -0.0649(7) 0.3251(2) 0.0229(15) Uani 1 1 d . . . C11B C 0.4559(4) 0.0634(7) 0.2898(2) 0.0236(15) Uani 1 1 d . . . C12B C 0.3859(5) 0.0662(7) 0.2603(2) 0.0271(16) Uani 1 1 d . . . C13B C 0.5818(4) 0.2429(7) 0.3947(2) 0.0233(15) Uani 1 1 d . . . C14B C 0.5300(4) 0.3738(7) 0.3993(2) 0.0259(16) Uani 1 1 d . . . H14B H 0.4837 0.3961 0.3756 0.031 Uiso 1 1 calc R . . C15B C 0.5466(4) 0.4698(8) 0.4385(2) 0.0278(16) Uani 1 1 d . . . H15B H 0.5128 0.5599 0.4408 0.033 Uiso 1 1 calc R . . C16B C 0.6112(4) 0.4378(7) 0.4744(2) 0.0281(16) Uani 1 1 d . . . H16B H 0.6214 0.5045 0.5014 0.034 Uiso 1 1 calc R . . C17B C 0.6610(4) 0.3072(8) 0.4707(2) 0.0275(16) Uani 1 1 d . . . H17B H 0.7048 0.2834 0.4957 0.033 Uiso 1 1 calc R . . C18B C 0.6474(4) 0.2103(8) 0.4307(2) 0.0254(16) Uani 1 1 d . . . H18B H 0.6829 0.1221 0.4280 0.030 Uiso 1 1 calc R . . C19B C 0.4274(4) -0.1992(7) 0.3320(2) 0.0219(15) Uani 1 1 d . . . C20B C 0.4159(4) -0.3062(8) 0.2944(2) 0.0272(16) Uani 1 1 d . . . H20B H 0.4463 -0.2935 0.2640 0.033 Uiso 1 1 calc R . . C21B C 0.3616(4) -0.4294(8) 0.3007(2) 0.0290(16) Uani 1 1 d . . . H21B H 0.3544 -0.5008 0.2747 0.035 Uiso 1 1 calc R . . C22B C 0.3167(4) -0.4489(8) 0.3457(2) 0.0293(16) Uani 1 1 d . . . H22B H 0.2781 -0.5327 0.3499 0.035 Uiso 1 1 calc R . . C23B C 0.3284(4) -0.3471(7) 0.3836(2) 0.0278(16) Uani 1 1 d . . . H23B H 0.2999 -0.3633 0.4144 0.033 Uiso 1 1 calc R . . C24B C 0.3822(4) -0.2194(7) 0.3771(2) 0.0253(15) Uani 1 1 d . . . H24B H 0.3882 -0.1473 0.4029 0.030 Uiso 1 1 calc R . . F1A F 0.6643(3) 0.0590(4) -0.03986(14) 0.0352(10) Uani 1 1 d . . . F2A F 0.5211(3) 0.0610(4) -0.05513(13) 0.0327(10) Uani 1 1 d . . . F3A F 0.3383(2) 0.3431(4) 0.03165(14) 0.0331(10) Uani 1 1 d . . . F4A F 0.3869(2) 0.2352(4) -0.03438(13) 0.0333(10) Uani 1 1 d . . . F1B F 0.5971(3) 0.4099(4) 0.29782(13) 0.0310(9) Uani 1 1 d . . . F2B F 0.5019(3) 0.3603(4) 0.23837(13) 0.0307(9) Uani 1 1 d . . . F3B F 0.3333(2) -0.0495(4) 0.24681(13) 0.0334(10) Uani 1 1 d . . . F4B F 0.3536(2) 0.1884(4) 0.23658(13) 0.0338(10) Uani 1 1 d . . . O1A O 0.6085(3) 0.4102(5) 0.06430(15) 0.0230(10) Uani 1 1 d . . . O1B O 0.4953(3) 0.0242(5) 0.37024(15) 0.0240(10) 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 C1A 0.024(4) 0.030(4) 0.030(4) -0.002(3) 0.000(3) -0.004(3) C2A 0.016(4) 0.031(4) 0.027(3) 0.005(3) 0.001(3) -0.003(3) C3A 0.019(4) 0.020(4) 0.030(3) 0.003(3) 0.000(3) 0.003(3) C4A 0.025(4) 0.025(4) 0.020(3) -0.004(3) 0.000(3) -0.003(3) C5A 0.030(4) 0.031(4) 0.032(4) -0.003(3) 0.004(3) 0.009(3) C6A 0.038(4) 0.025(4) 0.029(4) 0.001(3) 0.000(3) -0.003(3) C7A 0.033(4) 0.028(4) 0.028(4) 0.004(3) 0.003(3) 0.000(3) C8A 0.021(4) 0.029(4) 0.031(4) -0.001(3) 0.003(3) -0.008(3) C9A 0.024(4) 0.027(4) 0.031(4) -0.001(3) 0.001(3) -0.003(3) C10A 0.021(4) 0.024(4) 0.028(3) 0.002(3) 0.005(3) 0.001(3) C11A 0.023(4) 0.020(4) 0.026(3) 0.002(3) 0.004(3) 0.002(3) C12A 0.024(4) 0.029(4) 0.029(4) 0.000(3) 0.006(3) 0.002(3) C13A 0.020(4) 0.024(4) 0.025(3) -0.001(3) -0.001(3) -0.004(3) C14A 0.021(4) 0.035(4) 0.031(4) -0.002(3) 0.001(3) -0.001(3) C15A 0.029(4) 0.027(4) 0.030(4) 0.002(3) 0.003(3) -0.004(3) C16A 0.021(4) 0.029(4) 0.035(4) 0.000(3) 0.004(3) -0.005(3) C17A 0.024(4) 0.021(4) 0.045(4) -0.007(3) 0.003(3) 0.001(3) C18A 0.032(4) 0.020(4) 0.027(3) -0.002(3) -0.001(3) 0.001(3) C19A 0.027(4) 0.021(4) 0.024(3) 0.001(3) 0.000(3) 0.005(3) C20A 0.025(4) 0.023(4) 0.034(4) 0.001(3) -0.001(3) -0.004(3) C21A 0.034(4) 0.029(4) 0.036(4) -0.004(3) 0.004(3) -0.001(3) C22A 0.029(4) 0.036(4) 0.027(4) -0.007(3) 0.000(3) 0.006(3) C23A 0.028(4) 0.028(4) 0.033(4) 0.003(3) 0.001(3) -0.002(3) C24A 0.026(4) 0.035(4) 0.026(3) -0.001(3) 0.002(3) 0.009(3) C1B 0.025(4) 0.034(4) 0.030(4) -0.003(3) -0.001(3) 0.001(3) C2B 0.023(4) 0.021(4) 0.026(3) -0.002(3) 0.001(3) 0.001(3) C3B 0.022(4) 0.026(4) 0.029(3) -0.002(3) 0.003(3) -0.003(3) C4B 0.022(4) 0.019(3) 0.027(3) 0.000(3) -0.002(3) 0.000(3) C5B 0.021(4) 0.032(4) 0.027(3) 0.000(3) 0.002(3) 0.004(3) C6B 0.024(4) 0.042(5) 0.031(4) 0.007(3) 0.000(3) 0.004(4) C7B 0.032(4) 0.030(4) 0.031(4) 0.000(3) 0.005(3) 0.009(3) C8B 0.025(4) 0.027(4) 0.030(4) -0.002(3) -0.002(3) 0.003(3) C9B 0.021(4) 0.021(4) 0.031(3) 0.001(3) -0.002(3) 0.005(3) C10B 0.027(4) 0.028(4) 0.014(3) 0.000(3) -0.002(3) -0.003(3) C11B 0.025(4) 0.022(4) 0.024(3) 0.003(3) 0.000(3) 0.000(3) C12B 0.026(4) 0.024(4) 0.031(4) 0.001(3) 0.001(3) 0.005(3) C13B 0.020(4) 0.026(4) 0.024(3) -0.005(3) -0.002(3) -0.003(3) C14B 0.022(4) 0.031(4) 0.025(3) 0.005(3) -0.001(3) -0.004(3) C15B 0.024(4) 0.028(4) 0.031(4) -0.004(3) 0.001(3) -0.002(3) C16B 0.028(4) 0.026(4) 0.030(4) -0.006(3) 0.003(3) -0.003(3) C17B 0.024(4) 0.031(4) 0.028(4) -0.002(3) -0.004(3) 0.001(3) C18B 0.019(4) 0.030(4) 0.028(4) 0.001(3) 0.003(3) -0.001(3) C19B 0.018(3) 0.020(4) 0.027(3) -0.003(3) 0.002(3) -0.006(3) C20B 0.024(4) 0.031(4) 0.027(4) 0.003(3) -0.002(3) 0.000(3) C21B 0.024(4) 0.034(4) 0.029(4) 0.000(3) -0.007(3) -0.001(3) C22B 0.026(4) 0.028(4) 0.033(4) -0.003(3) -0.006(3) -0.010(3) C23B 0.025(4) 0.029(4) 0.030(4) 0.001(3) 0.003(3) -0.006(3) C24B 0.026(4) 0.023(4) 0.027(3) 0.000(3) -0.001(3) -0.002(3) F1A 0.034(2) 0.030(2) 0.043(2) -0.0048(18) 0.0105(19) 0.0019(19) F2A 0.035(2) 0.032(2) 0.031(2) -0.0041(17) -0.0017(18) -0.0078(19) F3A 0.023(2) 0.034(2) 0.041(2) -0.0040(18) -0.0020(18) 0.0014(18) F4A 0.029(2) 0.042(2) 0.029(2) -0.0036(18) -0.0056(17) -0.0051(19) F1B 0.035(2) 0.025(2) 0.033(2) 0.0023(17) 0.0034(18) -0.0018(19) F2B 0.037(2) 0.028(2) 0.027(2) 0.0049(16) -0.0002(17) 0.0006(18) F3B 0.029(2) 0.036(2) 0.035(2) 0.0023(17) -0.0095(17) -0.0039(19) F4B 0.030(2) 0.033(2) 0.038(2) 0.0106(18) -0.0079(18) 0.0024(19) O1A 0.019(2) 0.022(2) 0.028(2) -0.0015(19) 0.0013(19) -0.0026(19) O1B 0.023(2) 0.024(2) 0.025(2) -0.0001(19) -0.0002(19) -0.004(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 C1A F2A 1.309(8) . ? C1A C2A 1.328(9) . ? C1A F1A 1.346(8) . ? C2A C11A 1.487(9) . ? C2A C3A 1.517(9) . ? C3A O1A 1.471(7) . ? C3A C13A 1.520(9) . ? C3A C4A 1.527(8) . ? C4A C5A 1.374(9) . ? C4A C9A 1.400(9) . ? C5A C6A 1.396(9) . ? C5A H5A 0.9500 . ? C6A C7A 1.399(9) . ? C6A H6A 0.9500 . ? C7A C8A 1.383(9) . ? C7A H7A 0.9500 . ? C8A C9A 1.377(9) . ? C8A H8A 0.9500 . ? C9A C10A 1.538(9) . ? C10A O1A 1.466(7) . ? C10A C19A 1.510(9) . ? C10A C11A 1.543(9) . ? C11A C12A 1.293(9) . ? C12A F4A 1.337(7) . ? C12A F3A 1.344(7) . ? C13A C18A 1.386(9) . ? C13A C14A 1.390(9) . ? C14A C15A 1.390(9) . ? C14A H14A 0.9500 . ? C15A C16A 1.375(10) . ? C15A H15A 0.9500 . ? C16A C17A 1.387(9) . ? C16A H16A 0.9500 . ? C17A C18A 1.404(9) . ? C17A H17A 0.9500 . ? C18A H18A 0.9500 . ? C19A C20A 1.394(9) . ? C19A C24A 1.409(9) . ? C20A C21A 1.394(9) . ? C20A H20A 0.9500 . ? C21A C22A 1.392(9) . ? C21A H21A 0.9500 . ? C22A C23A 1.396(10) . ? C22A H22A 0.9500 . ? C23A C24A 1.378(9) . ? C23A H23A 0.9500 . ? C24A H24A 0.9500 . ? C1B F2B 1.317(7) . ? C1B C2B 1.331(9) . ? C1B F1B 1.331(8) . ? C2B C11B 1.466(9) . ? C2B C3B 1.544(9) . ? C3B O1B 1.463(7) . ? C3B C13B 1.509(9) . ? C3B C4B 1.523(9) . ? C4B C5B 1.377(9) . ? C4B C9B 1.411(9) . ? C5B C6B 1.377(9) . ? C5B H5B 0.9500 . ? C6B C7B 1.406(10) . ? C6B H6B 0.9500 . ? C7B C8B 1.414(9) . ? C7B H7B 0.9500 . ? C8B C9B 1.372(9) . ? C8B H8B 0.9500 . ? C9B C10B 1.548(9) . ? C10B O1B 1.456(7) . ? C10B C19B 1.501(9) . ? C10B C11B 1.552(9) . ? C11B C12B 1.295(9) . ? C12B F3B 1.340(8) . ? C12B F4B 1.347(7) . ? C13B C18B 1.390(9) . ? C13B C14B 1.404(9) . ? C14B C15B 1.377(9) . ? C14B H14B 0.9500 . ? C15B C16B 1.375(9) . ? C15B H15B 0.9500 . ? C16B C17B 1.384(9) . ? C16B H16B 0.9500 . ? C17B C18B 1.392(9) . ? C17B H17B 0.9500 . ? C18B H18B 0.9500 . ? C19B C20B 1.399(9) . ? C19B C24B 1.410(8) . ? C20B C21B 1.375(9) . ? C20B H20B 0.9500 . ? C21B C22B 1.404(9) . ? C21B H21B 0.9500 . ? C22B C23B 1.376(9) . ? C22B H22B 0.9500 . ? C23B C24B 1.403(9) . ? C23B H23B 0.9500 . ? C24B H24B 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 F2A C1A C2A 127.8(6) . . ? F2A C1A F1A 108.3(5) . . ? C2A C1A F1A 123.9(6) . . ? C1A C2A C11A 127.9(6) . . ? C1A C2A C3A 126.3(6) . . ? C11A C2A C3A 104.6(5) . . ? O1A C3A C2A 100.9(5) . . ? O1A C3A C13A 110.5(5) . . ? C2A C3A C13A 118.4(5) . . ? O1A C3A C4A 100.6(4) . . ? C2A C3A C4A 104.9(5) . . ? C13A C3A C4A 118.7(5) . . ? C5A C4A C9A 121.6(6) . . ? C5A C4A C3A 133.8(6) . . ? C9A C4A C3A 104.4(5) . . ? C4A C5A C6A 117.4(6) . . ? C4A C5A H5A 121.3 . . ? C6A C5A H5A 121.3 . . ? C5A C6A C7A 121.0(7) . . ? C5A C6A H6A 119.5 . . ? C7A C6A H6A 119.5 . . ? C8A C7A C6A 120.8(6) . . ? C8A C7A H7A 119.6 . . ? C6A C7A H7A 119.6 . . ? C9A C8A C7A 118.2(6) . . ? C9A C8A H8A 120.9 . . ? C7A C8A H8A 120.9 . . ? C8A C9A C4A 120.9(6) . . ? C8A C9A C10A 133.3(6) . . ? C4A C9A C10A 105.8(5) . . ? O1A C10A C19A 112.0(5) . . ? O1A C10A C9A 100.5(5) . . ? C19A C10A C9A 115.9(5) . . ? O1A C10A C11A 98.5(4) . . ? C19A C10A C11A 119.5(5) . . ? C9A C10A C11A 107.4(5) . . ? C12A C11A C2A 128.2(6) . . ? C12A C11A C10A 129.3(6) . . ? C2A C11A C10A 102.0(5) . . ? C11A C12A F4A 127.1(6) . . ? C11A C12A F3A 125.6(6) . . ? F4A C12A F3A 107.2(5) . . ? C18A C13A C14A 119.4(6) . . ? C18A C13A C3A 119.9(6) . . ? C14A C13A C3A 120.7(6) . . ? C13A C14A C15A 120.0(6) . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C16A C15A C14A 121.0(6) . . ? C16A C15A H15A 119.5 . . ? C14A C15A H15A 119.5 . . ? C15A C16A C17A 119.5(6) . . ? C15A C16A H16A 120.2 . . ? C17A C16A H16A 120.2 . . ? C16A C17A C18A 119.8(7) . . ? C16A C17A H17A 120.1 . . ? C18A C17A H17A 120.1 . . ? C13A C18A C17A 120.3(6) . . ? C13A C18A H18A 119.9 . . ? C17A C18A H18A 119.9 . . ? C20A C19A C24A 119.1(6) . . ? C20A C19A C10A 121.7(6) . . ? C24A C19A C10A 119.1(6) . . ? C21A C20A C19A 119.7(6) . . ? C21A C20A H20A 120.2 . . ? C19A C20A H20A 120.2 . . ? C22A C21A C20A 121.1(7) . . ? C22A C21A H21A 119.5 . . ? C20A C21A H21A 119.5 . . ? C21A C22A C23A 119.0(6) . . ? C21A C22A H22A 120.5 . . ? C23A C22A H22A 120.5 . . ? C24A C23A C22A 120.5(6) . . ? C24A C23A H23A 119.7 . . ? C22A C23A H23A 119.7 . . ? C23A C24A C19A 120.5(7) . . ? C23A C24A H24A 119.7 . . ? C19A C24A H24A 119.7 . . ? F2B C1B C2B 127.5(6) . . ? F2B C1B F1B 109.2(6) . . ? C2B C1B F1B 123.2(6) . . ? C1B C2B C11B 129.7(6) . . ? C1B C2B C3B 124.5(6) . . ? C11B C2B C3B 104.6(5) . . ? O1B C3B C13B 109.0(5) . . ? O1B C3B C4B 101.2(5) . . ? C13B C3B C4B 120.9(6) . . ? O1B C3B C2B 99.6(5) . . ? C13B C3B C2B 118.9(6) . . ? C4B C3B C2B 104.0(5) . . ? C5B C4B C9B 121.3(6) . . ? C5B C4B C3B 134.4(6) . . ? C9B C4B C3B 104.2(5) . . ? C4B C5B C6B 119.0(6) . . ? C4B C5B H5B 120.5 . . ? C6B C5B H5B 120.5 . . ? C5B C6B C7B 120.6(6) . . ? C5B C6B H6B 119.7 . . ? C7B C6B H6B 119.7 . . ? C6B C7B C8B 120.3(6) . . ? C6B C7B H7B 119.8 . . ? C8B C7B H7B 119.8 . . ? C9B C8B C7B 118.4(6) . . ? C9B C8B H8B 120.8 . . ? C7B C8B H8B 120.8 . . ? C8B C9B C4B 120.4(6) . . ? C8B C9B C10B 133.5(6) . . ? C4B C9B C10B 106.0(5) . . ? O1B C10B C19B 112.0(5) . . ? O1B C10B C9B 100.1(5) . . ? C19B C10B C9B 117.1(5) . . ? O1B C10B C11B 97.3(5) . . ? C19B C10B C11B 119.9(5) . . ? C9B C10B C11B 106.9(5) . . ? C12B C11B C2B 128.1(6) . . ? C12B C11B C10B 127.9(6) . . ? C2B C11B C10B 102.9(5) . . ? C11B C12B F3B 127.3(6) . . ? C11B C12B F4B 125.4(6) . . ? F3B C12B F4B 107.3(5) . . ? C18B C13B C14B 119.2(6) . . ? C18B C13B C3B 120.1(6) . . ? C14B C13B C3B 120.5(6) . . ? C15B C14B C13B 119.7(6) . . ? C15B C14B H14B 120.1 . . ? C13B C14B H14B 120.1 . . ? C16B C15B C14B 121.3(6) . . ? C16B C15B H15B 119.3 . . ? C14B C15B H15B 119.3 . . ? C15B C16B C17B 119.2(6) . . ? C15B C16B H16B 120.4 . . ? C17B C16B H16B 120.4 . . ? C16B C17B C18B 120.6(6) . . ? C16B C17B H17B 119.7 . . ? C18B C17B H17B 119.7 . . ? C13B C18B C17B 119.8(6) . . ? C13B C18B H18B 120.1 . . ? C17B C18B H18B 120.1 . . ? C20B C19B C24B 118.9(6) . . ? C20B C19B C10B 121.3(5) . . ? C24B C19B C10B 119.8(5) . . ? C21B C20B C19B 121.4(6) . . ? C21B C20B H20B 119.3 . . ? C19B C20B H20B 119.3 . . ? C20B C21B C22B 119.5(6) . . ? C20B C21B H21B 120.2 . . ? C22B C21B H21B 120.2 . . ? C23B C22B C21B 120.2(6) . . ? C23B C22B H22B 119.9 . . ? C21B C22B H22B 119.9 . . ? C22B C23B C24B 120.5(6) . . ? C22B C23B H23B 119.7 . . ? C24B C23B H23B 119.7 . . ? C23B C24B C19B 119.4(6) . . ? C23B C24B H24B 120.3 . . ? C19B C24B H24B 120.3 . . ? C10A O1A C3A 97.0(4) . . ? C10B O1B C3B 98.7(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.445 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.121