# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'T. Don Tilley' 'Katharine Geramita' 'Jennifer McBee' 'Rachel Segalman' 'Yuefei Tao.' _publ_contact_author_name 'Don Tilley ' _publ_contact_author_address ; Chemistry University of California, Berkeley 591 Tan Hall UC Berkeley Berkeley California 94720-1460 UNITED STATES OF AMERICA ; _publ_contact_author_email TDTILLEY@BERKELEY.EDU _publ_section_title ;Synthesis and Characterization of 2,7-bis(pentafluorophenylethynyl)-hexafluoroheterofluorenes: New Materials with High Electron Affinities ; # Attachment '3a.cif' data_kath51s _database_code_depnum_ccdc_archive 'CCDC 697514' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H10 F16 Ge' _chemical_formula_sum 'C40 H10 F16 Ge' _chemical_formula_weight 867.07 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ge Ge 0.1547 1.8001 '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 7.9222(16) _cell_length_b 15.049(3) _cell_length_c 15.823(3) _cell_angle_alpha 111.63(3) _cell_angle_beta 102.29(3) _cell_angle_gamma 101.99(3) _cell_volume 1626.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 1247 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 19.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max .17 _exptl_crystal_size_mid .07 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 1.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'Sadabs, 2004' _exptl_special_details ; ? ; _diffrn_ambient_temperature 1183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 9156 _diffrn_reflns_av_R_equivalents 0.1023 _diffrn_reflns_av_sigmaI/netI 0.1905 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 20.81 _reflns_number_total 3384 _reflns_number_gt 1788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^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 3384 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 0.543 _refine_ls_restrained_S_all 0.543 _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 Ge1 Ge -0.73461(9) -0.23492(5) -0.47483(4) 0.0353(2) Uani 1 1 d . . . F1 F -1.5853(4) -0.4887(2) -0.9267(2) 0.0541(10) Uani 1 1 d . . . F2 F -1.8931(5) -0.5692(2) -1.0790(2) 0.0638(11) Uani 1 1 d . . . F3 F -2.0270(5) -0.4491(2) -1.1464(2) 0.0670(11) Uani 1 1 d . . . F4 F -1.8509(4) -0.2469(2) -1.0646(2) 0.0550(10) Uani 1 1 d . . . F5 F -1.5470(4) -0.1665(2) -0.9125(2) 0.0486(9) Uani 1 1 d . . . F6 F -1.0833(4) -0.3331(2) -0.66736(19) 0.0454(9) Uani 1 1 d . . . F7 F -1.1011(4) -0.0321(2) -0.68927(19) 0.0461(9) Uani 1 1 d . . . F8 F -0.8166(4) 0.0720(2) -0.5391(2) 0.0450(9) Uani 1 1 d . . . F9 F -0.5546(4) 0.1478(2) -0.39467(19) 0.0448(9) Uani 1 1 d . . . F10 F -0.2774(4) 0.2016(2) -0.24406(19) 0.0443(9) Uani 1 1 d . . . F12 F 0.1273(4) -0.0419(2) -0.0689(2) 0.0573(10) Uani 1 1 d . . . F13 F 0.4313(4) 0.0198(3) 0.0806(2) 0.0650(11) Uani 1 1 d . . . F14 F 0.6045(5) 0.2192(3) 0.1905(2) 0.0757(11) Uani 1 1 d . . . F15 F 0.4728(4) 0.3567(2) 0.1522(2) 0.0698(11) Uani 1 1 d . . . F16 F 0.1686(4) 0.2956(2) 0.0035(2) 0.0558(10) Uani 1 1 d . . . C1 C -0.6172(7) -0.3259(4) -0.5413(4) 0.0320(15) Uani 1 1 d . . . C2 C -0.4829(9) -0.3489(4) -0.4907(4) 0.0569(19) Uani 1 1 d . . . H2A H -0.4515 -0.3219 -0.4242 0.068 Uiso 1 1 calc R . . C3 C -0.3938(9) -0.4112(5) -0.5368(5) 0.069(2) Uani 1 1 d . . . H3A H -0.3043 -0.4260 -0.5008 0.083 Uiso 1 1 calc R . . C4 C -0.4340(8) -0.4518(4) -0.6343(5) 0.0517(18) Uani 1 1 d . . . H4A H -0.3710 -0.4923 -0.6646 0.062 Uiso 1 1 calc R . . C5 C -0.5717(9) -0.4307(4) -0.6868(4) 0.0483(18) Uani 1 1 d . . . H5A H -0.6051 -0.4593 -0.7534 0.058 Uiso 1 1 calc R . . C6 C -0.6594(8) -0.3669(4) -0.6397(4) 0.0437(17) Uani 1 1 d . . . H6A H -0.7485 -0.3515 -0.6753 0.052 Uiso 1 1 calc R . . C7 C -0.8698(7) -0.2833(4) -0.4049(3) 0.0332(15) Uani 1 1 d . . . C8 C -0.9567(8) -0.2227(4) -0.3500(4) 0.0429(17) Uani 1 1 d . . . H8A H -0.9498 -0.1600 -0.3494 0.052 Uiso 1 1 calc R . . C9 C -1.0523(8) -0.2545(5) -0.2968(4) 0.0472(17) Uani 1 1 d . . . H9A H -1.1062 -0.2131 -0.2596 0.057 Uiso 1 1 calc R . . C10 C -1.0657(8) -0.3486(5) -0.3002(4) 0.0445(17) Uani 1 1 d . . . H10A H -1.1325 -0.3714 -0.2664 0.053 Uiso 1 1 calc R . . C11 C -0.9829(9) -0.4087(5) -0.3522(4) 0.0481(18) Uani 1 1 d . . . H11A H -0.9915 -0.4715 -0.3527 0.058 Uiso 1 1 calc R . . C12 C -0.8861(7) -0.3764(4) -0.4042(4) 0.0379(15) Uani 1 1 d . . . H12A H -0.8305 -0.4183 -0.4396 0.046 Uiso 1 1 calc R . . C13 C -1.6501(9) -0.4259(5) -0.9595(4) 0.0418(17) Uani 1 1 d . . . C14 C -1.8037(9) -0.4695(5) -1.0371(4) 0.0419(17) Uani 1 1 d . . . C15 C -1.8739(8) -0.4087(5) -1.0712(4) 0.0411(17) Uani 1 1 d . . . C16 C -1.7862(9) -0.3079(5) -1.0308(4) 0.0390(16) Uani 1 1 d . . . C17 C -1.6316(8) -0.2655(4) -0.9534(4) 0.0321(15) Uani 1 1 d . . . C18 C -1.5545(8) -0.3241(5) -0.9147(4) 0.0351(16) Uani 1 1 d . . . C19 C -1.3946(9) -0.2804(4) -0.8350(4) 0.0410(17) Uani 1 1 d . . . C20 C -1.2609(8) -0.2392(4) -0.7664(4) 0.0359(16) Uani 1 1 d . . . C21 C -1.1031(7) -0.1862(4) -0.6836(4) 0.0328(15) Uani 1 1 d . . . C22 C -1.0136(8) -0.2316(4) -0.6328(4) 0.0347(15) Uani 1 1 d . . . C23 C -0.8639(8) -0.1793(4) -0.5516(4) 0.0312(15) Uani 1 1 d . . . C24 C -0.7894(7) -0.0740(4) -0.5149(4) 0.0309(14) Uani 1 1 d . . . C25 C -0.8757(8) -0.0275(4) -0.5651(4) 0.0307(15) Uani 1 1 d . . . C26 C -1.0253(8) -0.0837(5) -0.6462(4) 0.0323(15) Uani 1 1 d . . . C27 C -0.6267(7) -0.0279(4) -0.4266(4) 0.0266(14) Uani 1 1 d . . . C28 C -0.5744(7) -0.0988(4) -0.3947(4) 0.0305(15) Uani 1 1 d . . . C29 C -0.4276(8) -0.0643(4) -0.3152(4) 0.0321(15) Uani 1 1 d . . . C30 C -0.3196(8) 0.0353(4) -0.2602(4) 0.0325(15) Uani 1 1 d . . . C31 C -0.3755(8) 0.1030(4) -0.2918(4) 0.0321(15) Uani 1 1 d . . . C32 C -0.5214(8) 0.0727(4) -0.3728(4) 0.0318(15) Uani 1 1 d . . . C33 C -0.1608(8) 0.0675(4) -0.1793(4) 0.0368(16) Uani 1 1 d . . . C34 C -0.0256(8) 0.0934(4) -0.1149(4) 0.0344(16) Uani 1 1 d . . . C35 C 0.1378(7) 0.1256(4) -0.0368(4) 0.0296(15) Uani 1 1 d . . . C36 C 0.2108(8) 0.0575(4) -0.0144(4) 0.0374(16) Uani 1 1 d . . . C37 C 0.3642(9) 0.0881(5) 0.0617(5) 0.0420(17) Uani 1 1 d . . . C38 C 0.4518(8) 0.1873(6) 0.1164(4) 0.0450(17) Uani 1 1 d . . . C39 C 0.3848(8) 0.2586(5) 0.0987(4) 0.0431(17) Uani 1 1 d . . . C40 C 0.2300(8) 0.2253(4) 0.0213(4) 0.0350(16) Uani 1 1 d . . . F11 F -0.3788(4) -0.1321(2) -0.28575(19) 0.0439(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 Ge1 0.0348(4) 0.0375(4) 0.0368(4) 0.0190(3) 0.0070(3) 0.0168(3) F1 0.065(3) 0.058(2) 0.055(2) 0.035(2) 0.0164(19) 0.032(2) F2 0.070(3) 0.049(2) 0.067(3) 0.028(2) 0.010(2) 0.013(2) F3 0.061(3) 0.072(3) 0.054(2) 0.027(2) -0.005(2) 0.017(2) F4 0.054(3) 0.067(2) 0.055(2) 0.037(2) 0.0083(18) 0.032(2) F5 0.055(2) 0.047(2) 0.048(2) 0.023(2) 0.0157(18) 0.0232(19) F6 0.042(2) 0.041(2) 0.043(2) 0.0174(19) -0.0012(17) 0.0106(17) F7 0.052(2) 0.063(2) 0.044(2) 0.0330(19) 0.0198(17) 0.0373(19) F8 0.050(2) 0.044(2) 0.053(2) 0.0285(19) 0.0193(18) 0.0219(18) F9 0.048(2) 0.039(2) 0.052(2) 0.0260(18) 0.0123(17) 0.0150(18) F10 0.044(2) 0.039(2) 0.048(2) 0.0181(18) 0.0120(17) 0.0129(18) F12 0.061(3) 0.045(2) 0.072(3) 0.031(2) 0.020(2) 0.020(2) F13 0.066(3) 0.082(3) 0.086(3) 0.063(2) 0.029(2) 0.044(2) F14 0.053(3) 0.111(3) 0.054(2) 0.039(2) -0.002(2) 0.020(2) F15 0.065(3) 0.047(2) 0.063(2) 0.003(2) 0.008(2) 0.002(2) F16 0.056(3) 0.042(2) 0.072(2) 0.024(2) 0.0161(19) 0.0230(19) C1 0.034(4) 0.036(4) 0.028(4) 0.013(3) 0.010(3) 0.018(3) C2 0.066(5) 0.067(5) 0.028(4) 0.004(4) 0.008(4) 0.040(4) C3 0.059(5) 0.074(5) 0.048(5) -0.004(4) 0.000(4) 0.044(4) C4 0.040(5) 0.054(4) 0.054(5) 0.011(4) 0.017(4) 0.021(4) C5 0.063(5) 0.043(4) 0.036(4) 0.011(4) 0.017(4) 0.023(4) C6 0.053(5) 0.035(4) 0.047(5) 0.021(4) 0.013(4) 0.017(4) C7 0.040(4) 0.033(4) 0.026(4) 0.011(3) 0.009(3) 0.016(3) C8 0.043(5) 0.042(4) 0.050(4) 0.029(4) 0.008(4) 0.013(4) C9 0.051(5) 0.059(5) 0.041(4) 0.027(4) 0.018(3) 0.023(4) C10 0.032(4) 0.062(5) 0.047(4) 0.039(4) 0.008(3) 0.005(4) C11 0.053(5) 0.042(4) 0.056(5) 0.027(4) 0.017(4) 0.019(4) C12 0.037(4) 0.036(4) 0.043(4) 0.020(3) 0.009(3) 0.017(3) C13 0.046(5) 0.069(5) 0.035(4) 0.038(4) 0.015(4) 0.035(4) C14 0.047(5) 0.042(5) 0.043(4) 0.023(4) 0.014(4) 0.019(4) C15 0.030(4) 0.052(5) 0.026(4) 0.014(4) -0.008(3) 0.005(4) C16 0.044(5) 0.057(5) 0.036(4) 0.031(4) 0.013(4) 0.032(4) C17 0.041(4) 0.029(4) 0.037(4) 0.018(4) 0.018(4) 0.020(4) C18 0.029(4) 0.042(4) 0.030(4) 0.013(4) 0.005(3) 0.011(4) C19 0.046(5) 0.050(4) 0.036(4) 0.019(4) 0.021(4) 0.023(4) C20 0.031(5) 0.051(4) 0.039(4) 0.023(4) 0.017(4) 0.024(4) C21 0.022(4) 0.043(4) 0.038(4) 0.021(4) 0.011(3) 0.011(3) C22 0.038(4) 0.032(4) 0.044(4) 0.024(4) 0.017(4) 0.011(3) C23 0.030(4) 0.047(4) 0.026(4) 0.021(3) 0.012(3) 0.018(3) C24 0.028(4) 0.035(4) 0.036(4) 0.016(3) 0.015(3) 0.014(3) C25 0.034(4) 0.031(4) 0.040(4) 0.023(4) 0.017(3) 0.017(3) C26 0.028(4) 0.059(5) 0.032(4) 0.035(4) 0.012(3) 0.027(4) C27 0.023(4) 0.033(4) 0.031(4) 0.014(3) 0.017(3) 0.013(3) C28 0.027(4) 0.049(4) 0.033(4) 0.024(3) 0.016(3) 0.029(3) C29 0.038(4) 0.034(4) 0.041(4) 0.023(4) 0.023(4) 0.021(4) C30 0.037(4) 0.038(4) 0.032(4) 0.019(4) 0.015(3) 0.017(4) C31 0.029(4) 0.027(4) 0.035(4) 0.009(3) 0.019(3) -0.002(3) C32 0.036(4) 0.043(5) 0.031(4) 0.023(4) 0.019(3) 0.022(4) C33 0.037(5) 0.040(4) 0.035(4) 0.013(3) 0.015(4) 0.017(3) C34 0.034(4) 0.036(4) 0.039(4) 0.019(3) 0.014(4) 0.013(3) C35 0.032(4) 0.028(4) 0.034(4) 0.015(4) 0.013(3) 0.015(3) C36 0.044(5) 0.027(4) 0.040(4) 0.013(4) 0.019(4) 0.006(4) C37 0.041(5) 0.057(5) 0.054(5) 0.042(5) 0.023(4) 0.024(4) C38 0.027(4) 0.068(5) 0.034(4) 0.025(4) -0.003(3) 0.010(4) C39 0.038(5) 0.031(4) 0.046(4) 0.010(4) 0.007(4) 0.001(4) C40 0.047(5) 0.032(4) 0.042(4) 0.022(4) 0.015(4) 0.028(4) F11 0.048(2) 0.044(2) 0.042(2) 0.0215(18) 0.0046(16) 0.0210(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 Ge1 C7 1.917(5) . ? Ge1 C1 1.931(5) . ? Ge1 C28 1.933(5) . ? Ge1 C23 1.949(5) . ? F1 C13 1.370(5) . ? F2 C14 1.348(6) . ? F3 C15 1.342(6) . ? F4 C16 1.353(5) . ? F5 C17 1.333(6) . ? F6 C22 1.358(6) . ? F7 C26 1.356(5) . ? F8 C25 1.343(5) . ? F9 C32 1.356(5) . ? F10 C31 1.350(5) . ? F12 C36 1.347(5) . ? F13 C37 1.348(6) . ? F14 C38 1.345(6) . ? F15 C39 1.335(6) . ? F16 C40 1.345(5) . ? C1 C2 1.373(6) . ? C1 C6 1.379(6) . ? C2 C3 1.378(7) . ? C2 H2A 0.9300 . ? C3 C4 1.368(7) . ? C3 H3A 0.9300 . ? C4 C5 1.390(7) . ? C4 H4A 0.9300 . ? C5 C6 1.390(7) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C12 1.385(6) . ? C7 C8 1.411(7) . ? C8 C9 1.389(7) . ? C8 H8A 0.9300 . ? C9 C10 1.377(6) . ? C9 H9A 0.9300 . ? C10 C11 1.361(7) . ? C10 H10A 0.9300 . ? C11 C12 1.381(7) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.363(7) . ? C13 C18 1.383(7) . ? C14 C15 1.373(7) . ? C15 C16 1.361(7) . ? C16 C17 1.366(7) . ? C17 C18 1.411(7) . ? C18 C19 1.410(7) . ? C19 C20 1.195(7) . ? C20 C21 1.426(7) . ? C21 C26 1.373(7) . ? C21 C22 1.406(6) . ? C22 C23 1.376(7) . ? C23 C24 1.408(7) . ? C24 C25 1.402(6) . ? C24 C27 1.498(7) . ? C25 C26 1.379(7) . ? C27 C32 1.392(7) . ? C27 C28 1.433(6) . ? C28 C29 1.360(6) . ? C29 F11 1.358(5) . ? C29 C30 1.388(7) . ? C30 C31 1.397(6) . ? C30 C33 1.435(7) . ? C31 C32 1.381(7) . ? C33 C34 1.187(7) . ? C34 C35 1.434(7) . ? C35 C40 1.368(7) . ? C35 C36 1.392(7) . ? C36 C37 1.368(7) . ? C37 C38 1.349(7) . ? C38 C39 1.381(7) . ? C39 C40 1.382(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 Ge1 C1 114.0(2) . . ? C7 Ge1 C28 110.6(2) . . ? C1 Ge1 C28 114.1(2) . . ? C7 Ge1 C23 114.1(2) . . ? C1 Ge1 C23 114.4(2) . . ? C28 Ge1 C23 86.7(2) . . ? C2 C1 C6 117.8(5) . . ? C2 C1 Ge1 120.4(4) . . ? C6 C1 Ge1 121.8(4) . . ? C1 C2 C3 121.1(5) . . ? C1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? C4 C3 C2 121.5(6) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.2 . . ? C3 C4 C5 118.2(6) . . ? C3 C4 H4A 120.9 . . ? C5 C4 H4A 120.9 . . ? C4 C5 C6 119.9(5) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C1 C6 C5 121.4(5) . . ? C1 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C12 C7 C8 116.9(5) . . ? C12 C7 Ge1 123.0(5) . . ? C8 C7 Ge1 120.1(4) . . ? C9 C8 C7 121.5(5) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C10 C9 C8 118.7(6) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C11 C10 C9 121.2(6) . . ? C11 C10 H10A 119.4 . . ? C9 C10 H10A 119.4 . . ? C10 C11 C12 120.0(6) . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C7 121.7(5) . . ? C11 C12 H12A 119.2 . . ? C7 C12 H12A 119.2 . . ? C14 C13 F1 116.9(6) . . ? C14 C13 C18 124.2(6) . . ? F1 C13 C18 118.8(5) . . ? F2 C14 C13 122.5(6) . . ? F2 C14 C15 118.9(6) . . ? C13 C14 C15 118.6(6) . . ? F3 C15 C16 119.8(6) . . ? F3 C15 C14 120.0(6) . . ? C16 C15 C14 120.2(6) . . ? F4 C16 C15 121.2(6) . . ? F4 C16 C17 118.4(6) . . ? C15 C16 C17 120.4(5) . . ? F5 C17 C16 120.6(5) . . ? F5 C17 C18 117.6(5) . . ? C16 C17 C18 121.8(5) . . ? C13 C18 C19 123.6(6) . . ? C13 C18 C17 114.7(5) . . ? C19 C18 C17 121.7(6) . . ? C20 C19 C18 177.0(6) . . ? C19 C20 C21 177.5(6) . . ? C26 C21 C22 113.9(5) . . ? C26 C21 C20 121.6(5) . . ? C22 C21 C20 124.5(5) . . ? F6 C22 C23 119.5(5) . . ? F6 C22 C21 116.5(5) . . ? C23 C22 C21 124.0(5) . . ? C22 C23 C24 120.3(5) . . ? C22 C23 Ge1 127.0(4) . . ? C24 C23 Ge1 112.7(4) . . ? C25 C24 C23 116.6(5) . . ? C25 C24 C27 129.3(5) . . ? C23 C24 C27 114.1(5) . . ? F8 C25 C26 116.6(5) . . ? F8 C25 C24 122.7(5) . . ? C26 C25 C24 120.7(5) . . ? F7 C26 C21 118.9(5) . . ? F7 C26 C25 116.5(5) . . ? C21 C26 C25 124.5(5) . . ? C32 C27 C28 116.8(5) . . ? C32 C27 C24 128.9(5) . . ? C28 C27 C24 114.3(5) . . ? C29 C28 C27 118.8(5) . . ? C29 C28 Ge1 129.0(4) . . ? C27 C28 Ge1 112.2(4) . . ? F11 C29 C28 118.3(5) . . ? F11 C29 C30 115.8(5) . . ? C28 C29 C30 125.9(5) . . ? C29 C30 C31 114.1(5) . . ? C29 C30 C33 123.8(5) . . ? C31 C30 C33 122.0(5) . . ? F10 C31 C32 118.4(5) . . ? F10 C31 C30 118.7(5) . . ? C32 C31 C30 122.8(5) . . ? F9 C32 C31 115.2(5) . . ? F9 C32 C27 123.2(5) . . ? C31 C32 C27 121.6(5) . . ? C34 C33 C30 177.4(6) . . ? C33 C34 C35 179.5(6) . . ? C40 C35 C36 115.9(5) . . ? C40 C35 C34 121.9(5) . . ? C36 C35 C34 122.1(5) . . ? F12 C36 C37 118.8(6) . . ? F12 C36 C35 119.0(5) . . ? C37 C36 C35 122.2(5) . . ? F13 C37 C38 119.7(6) . . ? F13 C37 C36 120.4(6) . . ? C38 C37 C36 119.8(6) . . ? F14 C38 C37 120.9(6) . . ? F14 C38 C39 118.4(6) . . ? C37 C38 C39 120.7(6) . . ? F15 C39 C38 120.6(6) . . ? F15 C39 C40 121.3(6) . . ? C38 C39 C40 118.0(5) . . ? F16 C40 C35 119.3(5) . . ? F16 C40 C39 117.4(5) . . ? C35 C40 C39 123.2(5) . . ? 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 C7 Ge1 C1 C2 -64.0(5) . . . . ? C28 Ge1 C1 C2 64.6(5) . . . . ? C23 Ge1 C1 C2 162.2(5) . . . . ? C7 Ge1 C1 C6 118.5(4) . . . . ? C28 Ge1 C1 C6 -113.0(5) . . . . ? C23 Ge1 C1 C6 -15.4(5) . . . . ? C6 C1 C2 C3 -0.3(9) . . . . ? Ge1 C1 C2 C3 -177.9(5) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? C2 C3 C4 C5 -1.7(10) . . . . ? C3 C4 C5 C6 2.4(9) . . . . ? C2 C1 C6 C5 1.1(8) . . . . ? Ge1 C1 C6 C5 178.7(4) . . . . ? C4 C5 C6 C1 -2.1(9) . . . . ? C1 Ge1 C7 C12 -1.7(5) . . . . ? C28 Ge1 C7 C12 -132.0(4) . . . . ? C23 Ge1 C7 C12 132.3(4) . . . . ? C1 Ge1 C7 C8 177.6(4) . . . . ? C28 Ge1 C7 C8 47.3(5) . . . . ? C23 Ge1 C7 C8 -48.5(5) . . . . ? C12 C7 C8 C9 0.7(8) . . . . ? Ge1 C7 C8 C9 -178.6(4) . . . . ? C7 C8 C9 C10 -1.7(8) . . . . ? C8 C9 C10 C11 1.9(8) . . . . ? C9 C10 C11 C12 -1.2(9) . . . . ? C10 C11 C12 C7 0.2(8) . . . . ? C8 C7 C12 C11 0.0(8) . . . . ? Ge1 C7 C12 C11 179.3(4) . . . . ? F1 C13 C14 F2 2.0(9) . . . . ? C18 C13 C14 F2 179.9(5) . . . . ? F1 C13 C14 C15 179.2(5) . . . . ? C18 C13 C14 C15 -2.9(10) . . . . ? F2 C14 C15 F3 -1.4(8) . . . . ? C13 C14 C15 F3 -178.7(5) . . . . ? F2 C14 C15 C16 -179.6(5) . . . . ? C13 C14 C15 C16 3.1(9) . . . . ? F3 C15 C16 F4 0.4(9) . . . . ? C14 C15 C16 F4 178.6(5) . . . . ? F3 C15 C16 C17 179.1(5) . . . . ? C14 C15 C16 C17 -2.7(9) . . . . ? F4 C16 C17 F5 0.0(8) . . . . ? C15 C16 C17 F5 -178.8(5) . . . . ? F4 C16 C17 C18 -179.3(5) . . . . ? C15 C16 C17 C18 2.0(9) . . . . ? C14 C13 C18 C19 -179.3(6) . . . . ? F1 C13 C18 C19 -1.4(9) . . . . ? C14 C13 C18 C17 2.1(9) . . . . ? F1 C13 C18 C17 180.0(4) . . . . ? F5 C17 C18 C13 179.1(5) . . . . ? C16 C17 C18 C13 -1.6(8) . . . . ? F5 C17 C18 C19 0.5(8) . . . . ? C16 C17 C18 C19 179.8(6) . . . . ? C13 C18 C19 C20 -155(13) . . . . ? C17 C18 C19 C20 23(13) . . . . ? C18 C19 C20 C21 -2(25) . . . . ? C19 C20 C21 C26 -24(15) . . . . ? C19 C20 C21 C22 156(15) . . . . ? C26 C21 C22 F6 -179.1(5) . . . . ? C20 C21 C22 F6 1.1(8) . . . . ? C26 C21 C22 C23 1.4(8) . . . . ? C20 C21 C22 C23 -178.4(5) . . . . ? F6 C22 C23 C24 179.8(5) . . . . ? C21 C22 C23 C24 -0.7(9) . . . . ? F6 C22 C23 Ge1 -1.1(8) . . . . ? C21 C22 C23 Ge1 178.4(4) . . . . ? C7 Ge1 C23 C22 -69.4(5) . . . . ? C1 Ge1 C23 C22 64.5(6) . . . . ? C28 Ge1 C23 C22 179.5(5) . . . . ? C7 Ge1 C23 C24 109.8(4) . . . . ? C1 Ge1 C23 C24 -116.3(4) . . . . ? C28 Ge1 C23 C24 -1.3(4) . . . . ? C22 C23 C24 C25 0.1(8) . . . . ? Ge1 C23 C24 C25 -179.2(4) . . . . ? C22 C23 C24 C27 -179.8(5) . . . . ? Ge1 C23 C24 C27 0.9(6) . . . . ? C23 C24 C25 F8 -178.6(5) . . . . ? C27 C24 C25 F8 1.3(8) . . . . ? C23 C24 C25 C26 -0.2(8) . . . . ? C27 C24 C25 C26 179.7(5) . . . . ? C22 C21 C26 F7 -179.7(4) . . . . ? C20 C21 C26 F7 0.2(8) . . . . ? C22 C21 C26 C25 -1.5(9) . . . . ? C20 C21 C26 C25 178.3(5) . . . . ? F8 C25 C26 F7 -2.3(7) . . . . ? C24 C25 C26 F7 179.2(4) . . . . ? F8 C25 C26 C21 179.5(5) . . . . ? C24 C25 C26 C21 1.0(9) . . . . ? C25 C24 C27 C32 -0.1(9) . . . . ? C23 C24 C27 C32 179.8(5) . . . . ? C25 C24 C27 C28 -179.7(5) . . . . ? C23 C24 C27 C28 0.2(7) . . . . ? C32 C27 C28 C29 0.1(7) . . . . ? C24 C27 C28 C29 179.7(5) . . . . ? C32 C27 C28 Ge1 179.1(4) . . . . ? C24 C27 C28 Ge1 -1.2(5) . . . . ? C7 Ge1 C28 C29 65.8(5) . . . . ? C1 Ge1 C28 C29 -64.5(5) . . . . ? C23 Ge1 C28 C29 -179.7(5) . . . . ? C7 Ge1 C28 C27 -113.2(4) . . . . ? C1 Ge1 C28 C27 116.6(4) . . . . ? C23 Ge1 C28 C27 1.4(4) . . . . ? C27 C28 C29 F11 -179.8(4) . . . . ? Ge1 C28 C29 F11 1.3(8) . . . . ? C27 C28 C29 C30 -0.3(9) . . . . ? Ge1 C28 C29 C30 -179.1(4) . . . . ? F11 C29 C30 C31 -179.1(4) . . . . ? C28 C29 C30 C31 1.3(9) . . . . ? F11 C29 C30 C33 2.6(8) . . . . ? C28 C29 C30 C33 -177.0(5) . . . . ? C29 C30 C31 F10 -178.9(5) . . . . ? C33 C30 C31 F10 -0.5(8) . . . . ? C29 C30 C31 C32 -2.3(8) . . . . ? C33 C30 C31 C32 176.1(5) . . . . ? F10 C31 C32 F9 -1.9(7) . . . . ? C30 C31 C32 F9 -178.5(4) . . . . ? F10 C31 C32 C27 178.9(5) . . . . ? C30 C31 C32 C27 2.3(9) . . . . ? C28 C27 C32 F9 179.8(4) . . . . ? C24 C27 C32 F9 0.2(9) . . . . ? C28 C27 C32 C31 -1.1(8) . . . . ? C24 C27 C32 C31 179.3(5) . . . . ? C29 C30 C33 C34 88(13) . . . . ? C31 C30 C33 C34 -91(13) . . . . ? C30 C33 C34 C35 109(82) . . . . ? C33 C34 C35 C40 -8(87) . . . . ? C33 C34 C35 C36 170(100) . . . . ? C40 C35 C36 F12 -179.7(5) . . . . ? C34 C35 C36 F12 1.3(8) . . . . ? C40 C35 C36 C37 0.7(8) . . . . ? C34 C35 C36 C37 -178.3(5) . . . . ? F12 C36 C37 F13 0.8(8) . . . . ? C35 C36 C37 F13 -179.6(5) . . . . ? F12 C36 C37 C38 179.0(5) . . . . ? C35 C36 C37 C38 -1.4(9) . . . . ? F13 C37 C38 F14 -0.7(9) . . . . ? C36 C37 C38 F14 -178.8(5) . . . . ? F13 C37 C38 C39 -179.6(5) . . . . ? C36 C37 C38 C39 2.3(10) . . . . ? F14 C38 C39 F15 1.9(9) . . . . ? C37 C38 C39 F15 -179.2(6) . . . . ? F14 C38 C39 C40 178.7(5) . . . . ? C37 C38 C39 C40 -2.4(9) . . . . ? C36 C35 C40 F16 179.3(4) . . . . ? C34 C35 C40 F16 -1.6(8) . . . . ? C36 C35 C40 C39 -0.9(9) . . . . ? C34 C35 C40 C39 178.2(5) . . . . ? F15 C39 C40 F16 -1.7(8) . . . . ? C38 C39 C40 F16 -178.5(5) . . . . ? F15 C39 C40 C35 178.5(5) . . . . ? C38 C39 C40 C35 1.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.358 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 # Attachment '4a.cif' data_kath52s _database_code_depnum_ccdc_archive 'CCDC 697515' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H5 F16 O P' _chemical_formula_sum 'C34 H5 F16 O P' _chemical_formula_weight 764.35 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' P P 0.1023 0.0942 '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 _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 13.798(13) _cell_length_b 5.938(5) _cell_length_c 35.27(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.599(16) _cell_angle_gamma 90.00 _cell_volume 2840(5) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 986 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 19.08 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Sadabs, 2004' _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 9224 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.1163 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 20.86 _reflns_number_total 2955 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0103P)^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 2955 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0491 _refine_ls_wR_factor_gt 0.0420 _refine_ls_goodness_of_fit_ref 0.798 _refine_ls_restrained_S_all 0.798 _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 P1 P 0.75895(9) 0.4211(2) 0.14731(4) 0.0343(4) Uani 1 1 d . . . F5 F 1.22030(16) 0.4800(4) 0.00504(7) 0.0471(8) Uani 1 1 d . . . F11 F 0.55730(17) 0.2742(4) 0.16662(7) 0.0426(8) Uani 1 1 d . . . F7 F 0.98689(17) 0.1405(4) 0.03032(7) 0.0447(8) Uani 1 1 d . . . F6 F 0.94588(16) 0.6563(4) 0.12677(7) 0.0434(8) Uani 1 1 d . . . F12 F 0.30388(17) 0.1203(4) 0.20658(7) 0.0505(8) Uani 1 1 d . . . F10 F 0.51209(16) -0.3335(4) 0.08008(7) 0.0444(8) Uani 1 1 d . . . F4 F 1.37563(18) 0.7017(4) -0.01309(8) 0.0514(8) Uani 1 1 d . . . F2 F 1.33535(17) 1.2813(4) 0.07296(7) 0.0472(8) Uani 1 1 d . . . F1 F 1.17884(18) 1.0590(4) 0.09220(7) 0.0469(8) Uani 1 1 d . . . F8 F 0.83486(16) -0.0942(4) 0.04158(7) 0.0437(7) Uani 1 1 d . . . F9 F 0.67352(17) -0.2337(4) 0.05523(7) 0.0454(8) Uani 1 1 d . . . F13 F 0.14793(18) -0.0003(4) 0.23831(8) 0.0541(8) Uani 1 1 d . . . F14 F 0.05317(19) -0.3960(4) 0.21723(8) 0.0568(9) Uani 1 1 d . . . O1 O 0.72391(18) 0.6551(4) 0.14890(8) 0.0376(9) Uani 1 1 d . . . F16 F 0.27415(17) -0.5528(4) 0.13511(8) 0.0519(8) Uani 1 1 d . . . F15 F 0.11550(16) -0.6687(4) 0.16536(7) 0.0523(8) Uani 1 1 d . . . F3 F 1.43253(18) 1.1028(4) 0.02115(7) 0.0495(8) Uani 1 1 d . . . C34 C 0.2926(4) -0.2131(8) 0.16950(14) 0.0326(14) Uani 1 1 d . . . C19 C 0.8556(4) 0.0928(7) 0.06312(13) 0.0284(13) Uani 1 1 d . . . C18 C 0.8000(4) 0.1656(7) 0.08962(13) 0.0282(13) Uani 1 1 d . . . C7 C 1.1965(3) 0.7632(7) 0.04936(14) 0.0273(13) Uani 1 1 d . . . C17 C 0.8354(3) 0.3555(7) 0.11168(12) 0.0281(13) Uani 1 1 d . . . C9 C 1.3052(4) 1.0841(8) 0.05675(14) 0.0323(14) Uani 1 1 d . . . C15 C 0.9691(3) 0.4097(8) 0.07744(14) 0.0295(13) Uani 1 1 d . . . C26 C 0.7055(3) 0.0782(7) 0.09786(13) 0.0271(12) Uani 1 1 d . . . C10 C 1.3553(4) 0.9924(8) 0.02972(15) 0.0320(14) Uani 1 1 d . . . C12 C 1.2479(4) 0.6779(8) 0.02231(14) 0.0313(14) Uani 1 1 d . . . C1 C 0.8213(3) 0.3201(7) 0.19299(12) 0.0289(13) Uani 1 1 d . . . C25 C 0.6479(4) -0.0973(8) 0.08247(14) 0.0326(14) Uani 1 1 d . . . C33 C 0.2434(4) -0.4135(8) 0.16044(14) 0.0343(14) Uani 1 1 d . . . C23 C 0.5288(4) -0.0300(8) 0.12380(14) 0.0319(14) Uani 1 1 d . . . C21 C 0.6737(3) 0.2051(7) 0.12705(13) 0.0240(13) Uani 1 1 d . . . C6 C 0.8633(3) 0.1098(7) 0.19884(13) 0.0354(13) Uani 1 1 d . . . H6A H 0.8596 0.0110 0.1782 0.042 Uiso 1 1 calc R . . C30 C 0.1795(4) -0.1336(8) 0.21179(14) 0.0396(14) Uani 1 1 d . . . C20 C 0.9382(4) 0.2146(8) 0.05761(14) 0.0333(14) Uani 1 1 d . . . C24 C 0.5621(4) -0.1503(8) 0.09493(15) 0.0328(14) Uani 1 1 d . . . C31 C 0.1313(4) -0.3362(9) 0.20167(16) 0.0412(15) Uani 1 1 d . . . C2 C 0.8248(3) 0.4621(7) 0.22404(14) 0.0364(13) Uani 1 1 d . . . H2A H 0.7958 0.6037 0.2205 0.044 Uiso 1 1 calc R . . C32 C 0.1632(4) -0.4739(8) 0.17557(15) 0.0354(14) Uani 1 1 d . . . C11 C 1.3266(4) 0.7892(9) 0.01333(13) 0.0367(14) Uani 1 1 d . . . C14 C 1.0506(4) 0.5385(8) 0.06857(13) 0.0382(15) Uani 1 1 d . . . C29 C 0.2584(4) -0.0761(8) 0.19602(14) 0.0330(14) Uani 1 1 d . . . C8 C 1.2263(4) 0.9700(8) 0.06554(13) 0.0311(13) Uani 1 1 d . . . C16 C 0.9152(4) 0.4708(7) 0.10586(14) 0.0324(14) Uani 1 1 d . . . C28 C 0.3749(4) -0.1496(8) 0.15289(15) 0.0390(16) Uani 1 1 d . . . C4 C 0.9151(3) 0.1877(9) 0.26570(14) 0.0460(15) Uani 1 1 d . . . H4A H 0.9477 0.1441 0.2901 0.055 Uiso 1 1 calc R . . C3 C 0.8714(3) 0.3957(8) 0.26048(13) 0.0479(15) Uani 1 1 d . . . H3A H 0.8730 0.4920 0.2814 0.057 Uiso 1 1 calc R . . C13 C 1.1166(4) 0.6429(8) 0.06001(13) 0.0375(15) Uani 1 1 d . . . C27 C 0.4426(4) -0.0975(8) 0.13868(15) 0.0374(16) Uani 1 1 d . . . C22 C 0.5882(4) 0.1521(7) 0.13800(13) 0.0323(14) Uani 1 1 d . . . C5 C 0.9108(3) 0.0437(7) 0.23487(15) 0.0448(15) Uani 1 1 d . . . H5A H 0.9398 -0.0979 0.2384 0.054 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 P1 0.0367(9) 0.0300(9) 0.0340(10) 0.0021(7) 0.0008(8) -0.0004(7) F5 0.060(2) 0.0406(18) 0.0391(19) -0.0065(14) 0.0044(15) -0.0074(14) F11 0.0414(19) 0.0456(17) 0.042(2) 0.0007(15) 0.0104(15) -0.0019(14) F7 0.045(2) 0.0540(18) 0.037(2) -0.0061(14) 0.0121(15) -0.0041(14) F6 0.0506(19) 0.0346(17) 0.0460(19) -0.0060(14) 0.0112(15) -0.0126(14) F12 0.0507(19) 0.0382(17) 0.062(2) -0.0067(14) 0.0100(15) -0.0108(15) F10 0.0405(19) 0.0495(18) 0.0425(19) -0.0045(14) 0.0054(14) -0.0126(14) F4 0.051(2) 0.062(2) 0.044(2) -0.0038(16) 0.0171(16) -0.0048(15) F2 0.055(2) 0.0361(18) 0.048(2) -0.0049(14) 0.0019(15) -0.0116(14) F1 0.050(2) 0.0475(18) 0.045(2) -0.0086(15) 0.0140(16) -0.0050(15) F8 0.0443(18) 0.0382(17) 0.0474(19) -0.0113(14) 0.0055(15) -0.0045(13) F9 0.046(2) 0.0456(18) 0.044(2) -0.0111(15) 0.0089(15) -0.0140(14) F13 0.051(2) 0.057(2) 0.059(2) -0.0092(16) 0.0217(17) -0.0001(14) F14 0.050(2) 0.0555(19) 0.069(2) -0.0040(15) 0.0219(18) -0.0075(16) O1 0.045(2) 0.0258(18) 0.040(2) 0.0033(15) 0.0047(16) 0.0083(15) F16 0.050(2) 0.0517(19) 0.055(2) -0.0130(16) 0.0113(16) -0.0066(15) F15 0.0456(19) 0.0428(18) 0.069(2) -0.0110(15) 0.0110(16) -0.0166(14) F3 0.043(2) 0.0612(19) 0.046(2) 0.0018(15) 0.0114(15) -0.0114(16) C34 0.030(4) 0.029(4) 0.037(4) 0.000(3) 0.002(3) -0.001(3) C19 0.028(4) 0.029(3) 0.026(4) -0.007(3) -0.001(3) -0.008(3) C18 0.036(4) 0.024(3) 0.022(3) 0.001(3) -0.002(3) 0.003(3) C7 0.023(4) 0.019(3) 0.038(4) 0.007(3) 0.001(3) -0.008(3) C17 0.039(4) 0.027(3) 0.017(3) 0.002(3) 0.002(3) -0.001(3) C9 0.037(4) 0.024(3) 0.034(4) 0.003(3) 0.000(3) -0.005(3) C15 0.027(4) 0.032(3) 0.027(4) 0.003(3) -0.001(3) -0.008(3) C26 0.027(4) 0.032(3) 0.022(3) 0.006(3) 0.005(3) 0.000(3) C10 0.026(4) 0.036(4) 0.032(4) 0.010(3) 0.001(3) -0.014(3) C12 0.036(4) 0.025(3) 0.033(4) -0.005(3) 0.007(3) -0.003(3) C1 0.034(3) 0.023(3) 0.029(3) -0.005(3) 0.006(3) -0.003(2) C25 0.033(4) 0.030(3) 0.032(4) -0.006(3) -0.002(3) -0.006(3) C33 0.038(4) 0.037(4) 0.028(4) -0.009(3) 0.008(3) 0.005(3) C23 0.031(4) 0.033(4) 0.030(4) 0.005(3) 0.001(3) -0.002(3) C21 0.019(3) 0.029(3) 0.025(4) 0.007(3) 0.006(3) -0.005(3) C6 0.046(3) 0.031(3) 0.030(4) -0.004(3) 0.010(3) -0.001(3) C30 0.048(4) 0.037(4) 0.036(4) -0.011(3) 0.010(3) 0.004(3) C20 0.036(4) 0.038(4) 0.025(4) 0.000(3) 0.003(3) 0.004(3) C24 0.030(4) 0.028(3) 0.035(4) 0.004(3) -0.008(3) -0.016(3) C31 0.026(4) 0.047(4) 0.052(4) 0.005(3) 0.011(3) -0.005(3) C2 0.039(4) 0.032(3) 0.038(4) 0.002(3) 0.007(3) 0.003(2) C32 0.035(4) 0.028(4) 0.043(4) -0.009(3) 0.006(3) -0.003(3) C11 0.045(4) 0.047(4) 0.021(4) 0.000(3) 0.013(3) 0.000(3) C14 0.045(5) 0.042(4) 0.025(4) 0.004(3) 0.001(3) 0.005(3) C29 0.033(4) 0.030(3) 0.036(4) 0.004(3) 0.005(3) -0.009(3) C8 0.034(4) 0.039(4) 0.022(4) 0.002(3) 0.011(3) 0.002(3) C16 0.046(4) 0.019(3) 0.026(4) -0.005(3) -0.007(3) -0.005(3) C28 0.041(5) 0.032(3) 0.037(4) 0.006(3) -0.011(3) 0.001(3) C4 0.049(4) 0.048(4) 0.035(4) 0.007(3) -0.011(3) -0.007(3) C3 0.067(4) 0.048(4) 0.027(4) -0.016(3) 0.006(3) -0.007(3) C13 0.041(4) 0.040(4) 0.030(4) 0.002(3) 0.002(3) 0.000(3) C27 0.036(5) 0.030(3) 0.040(4) -0.002(3) -0.010(3) -0.005(3) C22 0.046(4) 0.031(4) 0.018(3) -0.003(3) 0.000(3) 0.008(3) C5 0.053(4) 0.031(3) 0.046(4) 0.006(3) -0.004(3) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.476(3) . ? P1 C1 1.785(4) . ? P1 C21 1.797(4) . ? P1 C17 1.825(5) . ? F5 C12 1.346(5) . ? F11 C22 1.372(5) . ? F7 C20 1.346(5) . ? F6 C16 1.349(4) . ? F12 C29 1.344(4) . ? F10 C24 1.342(4) . ? F4 C11 1.352(5) . ? F2 C9 1.335(5) . ? F1 C8 1.349(5) . ? F8 C19 1.346(4) . ? F9 C25 1.352(5) . ? F13 C30 1.357(5) . ? F14 C31 1.345(5) . ? F16 C33 1.342(5) . ? F15 C32 1.347(5) . ? F3 C10 1.333(5) . ? C34 C33 1.378(6) . ? C34 C29 1.386(6) . ? C34 C28 1.421(6) . ? C19 C18 1.382(6) . ? C19 C20 1.393(5) . ? C18 C17 1.406(5) . ? C18 C26 1.481(6) . ? C7 C8 1.384(5) . ? C7 C12 1.386(6) . ? C7 C13 1.421(6) . ? C17 C16 1.344(5) . ? C9 C8 1.365(6) . ? C9 C10 1.387(6) . ? C15 C20 1.380(5) . ? C15 C16 1.402(6) . ? C15 C14 1.441(6) . ? C26 C25 1.362(5) . ? C26 C21 1.410(5) . ? C10 C11 1.365(6) . ? C12 C11 1.357(6) . ? C1 C6 1.376(5) . ? C1 C2 1.376(5) . ? C25 C24 1.373(6) . ? C33 C32 1.362(6) . ? C23 C24 1.389(6) . ? C23 C22 1.393(6) . ? C23 C27 1.442(6) . ? C21 C22 1.344(6) . ? C6 C5 1.375(5) . ? C6 H6A 0.9300 . ? C30 C29 1.354(6) . ? C30 C31 1.389(6) . ? C31 C32 1.363(6) . ? C2 C3 1.384(5) . ? C2 H2A 0.9300 . ? C14 C13 1.186(6) . ? C28 C27 1.180(6) . ? C4 C3 1.372(5) . ? C4 C5 1.376(5) . ? C4 H4A 0.9300 . ? C3 H3A 0.9300 . ? C5 H5A 0.9300 . ? 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 O1 P1 C1 112.9(2) . . ? O1 P1 C21 119.47(19) . . ? C1 P1 C21 106.89(19) . . ? O1 P1 C17 117.51(19) . . ? C1 P1 C17 107.8(2) . . ? C21 P1 C17 89.6(2) . . ? C33 C34 C29 116.7(5) . . ? C33 C34 C28 122.0(5) . . ? C29 C34 C28 121.3(5) . . ? F8 C19 C18 123.6(4) . . ? F8 C19 C20 116.4(5) . . ? C18 C19 C20 120.1(5) . . ? C19 C18 C17 116.5(5) . . ? C19 C18 C26 129.9(5) . . ? C17 C18 C26 113.6(5) . . ? C8 C7 C12 117.2(5) . . ? C8 C7 C13 121.6(5) . . ? C12 C7 C13 121.2(5) . . ? C16 C17 C18 122.3(5) . . ? C16 C17 P1 126.2(4) . . ? C18 C17 P1 111.5(4) . . ? F2 C9 C8 122.4(5) . . ? F2 C9 C10 118.9(5) . . ? C8 C9 C10 118.7(5) . . ? C20 C15 C16 115.1(5) . . ? C20 C15 C14 121.1(5) . . ? C16 C15 C14 123.8(5) . . ? C25 C26 C21 117.5(5) . . ? C25 C26 C18 131.3(5) . . ? C21 C26 C18 111.1(4) . . ? F3 C10 C11 121.4(5) . . ? F3 C10 C9 118.9(5) . . ? C11 C10 C9 119.7(5) . . ? F5 C12 C11 119.5(5) . . ? F5 C12 C7 119.5(5) . . ? C11 C12 C7 121.0(5) . . ? C6 C1 C2 119.0(4) . . ? C6 C1 P1 124.1(4) . . ? C2 C1 P1 116.9(3) . . ? F9 C25 C26 122.1(5) . . ? F9 C25 C24 116.3(4) . . ? C26 C25 C24 121.5(5) . . ? F16 C33 C32 118.5(5) . . ? F16 C33 C34 119.0(5) . . ? C32 C33 C34 122.5(5) . . ? C24 C23 C22 114.2(5) . . ? C24 C23 C27 122.0(5) . . ? C22 C23 C27 123.7(5) . . ? C22 C21 C26 119.5(4) . . ? C22 C21 P1 126.7(4) . . ? C26 C21 P1 113.7(4) . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? C29 C30 F13 121.4(5) . . ? C29 C30 C31 119.7(5) . . ? F13 C30 C31 118.9(5) . . ? F7 C20 C15 119.2(5) . . ? F7 C20 C19 117.3(5) . . ? C15 C20 C19 123.4(5) . . ? F10 C24 C25 118.2(5) . . ? F10 C24 C23 119.1(5) . . ? C25 C24 C23 122.5(5) . . ? F14 C31 C32 120.0(5) . . ? F14 C31 C30 120.4(5) . . ? C32 C31 C30 119.6(5) . . ? C1 C2 C3 120.5(4) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? F15 C32 C33 120.9(5) . . ? F15 C32 C31 119.5(5) . . ? C33 C32 C31 119.5(5) . . ? F4 C11 C12 119.8(5) . . ? F4 C11 C10 119.2(5) . . ? C12 C11 C10 120.9(5) . . ? C13 C14 C15 177.8(5) . . ? F12 C29 C30 118.3(5) . . ? F12 C29 C34 119.8(5) . . ? C30 C29 C34 121.9(5) . . ? F1 C8 C9 118.3(5) . . ? F1 C8 C7 119.3(5) . . ? C9 C8 C7 122.4(5) . . ? C17 C16 F6 121.1(5) . . ? C17 C16 C15 122.4(4) . . ? F6 C16 C15 116.6(5) . . ? C27 C28 C34 179.2(6) . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C14 C13 C7 178.6(6) . . ? C28 C27 C23 176.3(6) . . ? C21 C22 F11 119.7(4) . . ? C21 C22 C23 124.6(5) . . ? F11 C22 C23 115.6(5) . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? 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 F8 C19 C18 C17 175.8(4) . . . . ? C20 C19 C18 C17 -4.1(6) . . . . ? F8 C19 C18 C26 -6.4(7) . . . . ? C20 C19 C18 C26 173.7(4) . . . . ? C19 C18 C17 C16 4.3(6) . . . . ? C26 C18 C17 C16 -173.9(4) . . . . ? C19 C18 C17 P1 -176.5(3) . . . . ? C26 C18 C17 P1 5.4(4) . . . . ? O1 P1 C17 C16 49.7(4) . . . . ? C1 P1 C17 C16 -79.2(4) . . . . ? C21 P1 C17 C16 173.2(4) . . . . ? O1 P1 C17 C18 -129.5(3) . . . . ? C1 P1 C17 C18 101.6(3) . . . . ? C21 P1 C17 C18 -6.0(3) . . . . ? C19 C18 C26 C25 1.1(8) . . . . ? C17 C18 C26 C25 178.9(4) . . . . ? C19 C18 C26 C21 -179.2(4) . . . . ? C17 C18 C26 C21 -1.4(5) . . . . ? F2 C9 C10 F3 0.8(6) . . . . ? C8 C9 C10 F3 -179.8(4) . . . . ? F2 C9 C10 C11 178.9(4) . . . . ? C8 C9 C10 C11 -1.7(7) . . . . ? C8 C7 C12 F5 -178.4(3) . . . . ? C13 C7 C12 F5 1.7(7) . . . . ? C8 C7 C12 C11 2.5(7) . . . . ? C13 C7 C12 C11 -177.4(4) . . . . ? O1 P1 C1 C6 -178.0(3) . . . . ? C21 P1 C1 C6 48.7(4) . . . . ? C17 P1 C1 C6 -46.5(4) . . . . ? O1 P1 C1 C2 3.4(4) . . . . ? C21 P1 C1 C2 -129.9(4) . . . . ? C17 P1 C1 C2 134.9(4) . . . . ? C21 C26 C25 F9 -177.8(4) . . . . ? C18 C26 C25 F9 1.9(7) . . . . ? C21 C26 C25 C24 -0.3(6) . . . . ? C18 C26 C25 C24 179.4(4) . . . . ? C29 C34 C33 F16 -179.5(4) . . . . ? C28 C34 C33 F16 -0.1(6) . . . . ? C29 C34 C33 C32 2.0(7) . . . . ? C28 C34 C33 C32 -178.6(4) . . . . ? C25 C26 C21 C22 -1.2(6) . . . . ? C18 C26 C21 C22 179.0(4) . . . . ? C25 C26 C21 P1 176.4(3) . . . . ? C18 C26 C21 P1 -3.4(4) . . . . ? O1 P1 C21 C22 -55.5(4) . . . . ? C1 P1 C21 C22 74.2(4) . . . . ? C17 P1 C21 C22 -177.3(4) . . . . ? O1 P1 C21 C26 127.2(3) . . . . ? C1 P1 C21 C26 -103.2(3) . . . . ? C17 P1 C21 C26 5.4(3) . . . . ? C2 C1 C6 C5 -1.9(7) . . . . ? P1 C1 C6 C5 179.6(3) . . . . ? C16 C15 C20 F7 -178.7(4) . . . . ? C14 C15 C20 F7 1.9(6) . . . . ? C16 C15 C20 C19 4.1(7) . . . . ? C14 C15 C20 C19 -175.2(4) . . . . ? F8 C19 C20 F7 2.8(6) . . . . ? C18 C19 C20 F7 -177.3(4) . . . . ? F8 C19 C20 C15 180.0(4) . . . . ? C18 C19 C20 C15 -0.1(7) . . . . ? F9 C25 C24 F10 1.5(6) . . . . ? C26 C25 C24 F10 -176.1(4) . . . . ? F9 C25 C24 C23 177.5(4) . . . . ? C26 C25 C24 C23 -0.1(7) . . . . ? C22 C23 C24 F10 177.9(3) . . . . ? C27 C23 C24 F10 0.8(7) . . . . ? C22 C23 C24 C25 1.9(7) . . . . ? C27 C23 C24 C25 -175.2(4) . . . . ? C29 C30 C31 F14 179.6(4) . . . . ? F13 C30 C31 F14 1.7(7) . . . . ? C29 C30 C31 C32 -0.9(7) . . . . ? F13 C30 C31 C32 -178.8(4) . . . . ? C6 C1 C2 C3 1.0(7) . . . . ? P1 C1 C2 C3 179.7(3) . . . . ? F16 C33 C32 F15 -0.1(7) . . . . ? C34 C33 C32 F15 178.4(4) . . . . ? F16 C33 C32 C31 179.3(4) . . . . ? C34 C33 C32 C31 -2.2(7) . . . . ? F14 C31 C32 F15 0.5(7) . . . . ? C30 C31 C32 F15 -179.0(4) . . . . ? F14 C31 C32 C33 -178.9(4) . . . . ? C30 C31 C32 C33 1.6(7) . . . . ? F5 C12 C11 F4 0.7(7) . . . . ? C7 C12 C11 F4 179.8(4) . . . . ? F5 C12 C11 C10 178.6(4) . . . . ? C7 C12 C11 C10 -2.3(7) . . . . ? F3 C10 C11 F4 -2.2(7) . . . . ? C9 C10 C11 F4 179.8(4) . . . . ? F3 C10 C11 C12 179.9(4) . . . . ? C9 C10 C11 C12 1.8(7) . . . . ? C20 C15 C14 C13 38(15) . . . . ? C16 C15 C14 C13 -141(15) . . . . ? F13 C30 C29 F12 -1.7(7) . . . . ? C31 C30 C29 F12 -179.6(4) . . . . ? F13 C30 C29 C34 178.7(4) . . . . ? C31 C30 C29 C34 0.7(7) . . . . ? C33 C34 C29 F12 179.0(4) . . . . ? C28 C34 C29 F12 -0.4(6) . . . . ? C33 C34 C29 C30 -1.3(7) . . . . ? C28 C34 C29 C30 179.3(4) . . . . ? F2 C9 C8 F1 -1.4(6) . . . . ? C10 C9 C8 F1 179.2(4) . . . . ? F2 C9 C8 C7 -178.6(4) . . . . ? C10 C9 C8 C7 2.1(7) . . . . ? C12 C7 C8 F1 -179.6(4) . . . . ? C13 C7 C8 F1 0.3(6) . . . . ? C12 C7 C8 C9 -2.4(7) . . . . ? C13 C7 C8 C9 177.5(4) . . . . ? C18 C17 C16 F6 178.2(3) . . . . ? P1 C17 C16 F6 -1.0(6) . . . . ? C18 C17 C16 C15 -0.2(7) . . . . ? P1 C17 C16 C15 -179.3(3) . . . . ? C20 C15 C16 C17 -4.0(7) . . . . ? C14 C15 C16 C17 175.4(4) . . . . ? C20 C15 C16 F6 177.6(3) . . . . ? C14 C15 C16 F6 -3.0(6) . . . . ? C33 C34 C28 C27 47(44) . . . . ? C29 C34 C28 C27 -134(44) . . . . ? C5 C4 C3 C2 -1.4(7) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C15 C14 C13 C7 -60(31) . . . . ? C8 C7 C13 C14 -163(100) . . . . ? C12 C7 C13 C14 17(24) . . . . ? C34 C28 C27 C23 -180(100) . . . . ? C24 C23 C27 C28 140(8) . . . . ? C22 C23 C27 C28 -37(9) . . . . ? C26 C21 C22 F11 179.5(4) . . . . ? P1 C21 C22 F11 2.3(6) . . . . ? C26 C21 C22 C23 3.3(7) . . . . ? P1 C21 C22 C23 -173.9(3) . . . . ? C24 C23 C22 C21 -3.6(7) . . . . ? C27 C23 C22 C21 173.5(4) . . . . ? C24 C23 C22 F11 -179.9(4) . . . . ? C27 C23 C22 F11 -2.9(6) . . . . ? C1 C6 C5 C4 1.1(7) . . . . ? C3 C4 C5 C6 0.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 20.86 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.236 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.054