# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Dillon, K.' 'Capel, Victoria' 'Goeta, Andres' 'Howard, Judith' 'Monks, Philippa' 'Probert, Michael' 'Shepherd, Helena' 'Zorina, Natalia' _publ_contact_author_name 'Dillon, K.' _publ_contact_author_email K.B.Dillon@durham.ac.uk _publ_section_title ; Stereochemically inactive lone pairs in phosphorus(III) compounds: the characterisation of some derivatives with the 2,5-(CF3)2C6H3 (Ar) substituent and their complexation behaviour towards Pt(II) species. ; #TrackingRef '- Ar2PCl_cif.cif' _publ_requested_journal ? # Attachment '- Ar2PCl_cif.cif' data_AR2PCL _database_code_depnum_ccdc_archive 'CCDC 795645' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C16 H6 Cl F12 P' _chemical_formula_sum 'C16 H6 Cl F12 P' _chemical_formula_weight 492.63 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_IT_number 2 _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_angle_alpha 72.765(3) _cell_angle_beta 72.896(3) _cell_angle_gamma 78.100(3) _cell_formula_units_Z 2 _cell_length_a 8.400(2) _cell_length_b 10.220(3) _cell_length_c 11.474(3) _cell_measurement_reflns_used 2799 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.37 _cell_measurement_theta_min 2.47 _cell_volume 891.4(4) _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.738833 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0373 before and 0.0307 after correction. The Ratio of minimum to maximum transmission is 0.738833. The \l/2 correction factor is 0.0000 ; _exptl_crystal_F_000 484 _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (30.00 s exposure) covering -1.000\ degrees in \w. The crystal to detector distance was 4.424 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.0 _diffrn_detector_type 'Bruker SMART CCD 1K area detector' _diffrn_measured_fraction_theta_full 0.883 _diffrn_measured_fraction_theta_max 0.883 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'BRUKER SMART CCD 1000' _diffrn_measurement_method 'phi and omega scans' _diffrn_orient_matrix_UB_11 0.100987 _diffrn_orient_matrix_UB_12 0.044677 _diffrn_orient_matrix_UB_13 0.00546 _diffrn_orient_matrix_UB_21 0.006997 _diffrn_orient_matrix_UB_22 0.003411 _diffrn_orient_matrix_UB_23 0.054232 _diffrn_orient_matrix_UB_31 0.034737 _diffrn_orient_matrix_UB_32 -0.056338 _diffrn_orient_matrix_UB_33 -0.007615 _diffrn_radiation_monochromator Parallel,graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9022 _diffrn_reflns_theta_full 30.23 _diffrn_reflns_theta_max 30.22 _diffrn_reflns_theta_min 1.92 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 5.0 _diffrn_source_power 0.1 _diffrn_source_target Mo _diffrn_source_voltage 20.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2954 _reflns_number_total 4696 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.049 (Bruker, 1999)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.663 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.087 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0591 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 4696 _refine_ls_number_restraints 54 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1085 _refine_ls_wR_factor_ref 0.1253 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+1.1498P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.40867(10) 0.63311(8) 0.05018(7) 0.01834(19) Uani 1 1 d . . . Cl1 Cl 0.64435(10) 0.65757(9) 0.05598(8) 0.0283(2) Uani 1 1 d . . . F7B3 F 0.2611(3) 0.7916(2) -0.18224(18) 0.0322(5) Uani 1 1 d . . . F7B1 F 0.5052(3) 0.8413(2) -0.19822(19) 0.0392(5) Uani 1 1 d . . . F7A3 F -0.0489(3) 0.4458(2) 0.1857(2) 0.0508(7) Uani 1 1 d . . . F7B2 F 0.3140(3) 1.0017(2) -0.26076(19) 0.0532(7) Uani 1 1 d . . . F7A2 F -0.0846(3) 0.6342(3) 0.2420(2) 0.0513(7) Uani 1 1 d . . . F8A2 F 0.4578(3) 0.2922(3) 0.6021(2) 0.0492(6) Uani 1 1 d . . . C1A C 0.3319(4) 0.5240(3) 0.2114(3) 0.0168(6) Uani 1 1 d . . . C2B C 0.2441(4) 0.8377(3) 0.1840(3) 0.0198(6) Uani 1 1 d . . . H2B H 0.2598 0.7683 0.2574 0.024 Uiso 1 1 calc R . . F8A3 F 0.6586(3) 0.3591(3) 0.4441(2) 0.0670(9) Uani 1 1 d . . . C1B C 0.3024(4) 0.8073(3) 0.0669(3) 0.0186(6) Uani 1 1 d . . . C2A C 0.4448(4) 0.4614(3) 0.2874(3) 0.0211(7) Uani 1 1 d . . . H2A H 0.5567 0.4831 0.2594 0.025 Uiso 1 1 calc R . . F8A1 F 0.5696(3) 0.1667(3) 0.4736(2) 0.0599(8) Uani 1 1 d . . . C6B C 0.2793(4) 0.9128(3) -0.0402(3) 0.0234(7) Uani 1 1 d . . . C3B C 0.1629(4) 0.9687(3) 0.1950(3) 0.0215(7) Uani 1 1 d . A . C7A C 0.0314(4) 0.5439(3) 0.1878(3) 0.0253(7) Uani 1 1 d . . . C3A C 0.3948(4) 0.3679(3) 0.4031(3) 0.0222(7) Uani 1 1 d . . . C8B C 0.1024(4) 0.9973(3) 0.3232(3) 0.0283(8) Uani 1 1 d D . . C6A C 0.1678(4) 0.4870(3) 0.2572(3) 0.0191(6) Uani 1 1 d . . . C5B C 0.1994(4) 1.0440(3) -0.0289(3) 0.0286(8) Uani 1 1 d . A . H5B H 0.1857 1.1148 -0.1020 0.034 Uiso 1 1 calc R . . C4B C 0.1396(4) 1.0712(3) 0.0893(3) 0.0271(8) Uani 1 1 d . . . H4B H 0.0830 1.1599 0.0973 0.033 Uiso 1 1 calc R A . C5A C 0.1206(4) 0.3937(3) 0.3732(3) 0.0262(7) Uani 1 1 d . . . H5A H 0.0090 0.3713 0.4025 0.031 Uiso 1 1 calc R . . C7B C 0.3398(5) 0.8878(3) -0.1701(3) 0.0295(8) Uani 1 1 d . . . C4A C 0.2337(4) 0.3329(3) 0.4468(3) 0.0273(8) Uani 1 1 d . . . H4A H 0.2011 0.2685 0.5257 0.033 Uiso 1 1 calc R . . C8A C 0.5210(5) 0.2970(4) 0.4801(3) 0.0312(8) Uani 1 1 d . . . F8B8 F 0.2115(10) 0.9500(9) 0.3875(8) 0.0295(5) Uiso 0.25 1 d PD A 1 F8B9 F 0.0672(10) 1.1372(7) 0.3064(8) 0.0295(5) Uiso 0.25 1 d PD A 1 F8B7 F -0.0452(9) 0.9477(9) 0.3795(7) 0.0295(5) Uiso 0.25 1 d PD A 1 F8B1 F 0.0140(5) 0.8992(4) 0.4057(4) 0.0295(5) Uiso 0.50 1 d PD A 2 F8B2 F 0.2355(6) 1.0003(4) 0.3674(5) 0.0295(5) Uiso 0.50 1 d PD A 2 F8B3 F 0.0057(5) 1.1214(4) 0.3221(4) 0.0295(5) Uiso 0.50 1 d PD A 2 F8B4 F 0.0804(11) 0.8757(7) 0.4229(7) 0.0295(5) Uiso 0.25 1 d PD A 3 F8B5 F 0.2125(11) 1.0425(9) 0.3611(9) 0.0295(5) Uiso 0.25 1 d PD A 3 F8B6 F -0.0392(9) 1.0789(8) 0.3464(8) 0.0295(5) Uiso 0.25 1 d PD A 3 F7A1 F 0.0855(2) 0.6132(2) 0.06735(17) 0.0300(5) 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 P1 0.0188(4) 0.0158(4) 0.0188(4) -0.0034(3) -0.0043(3) -0.0008(3) Cl1 0.0206(4) 0.0307(5) 0.0329(5) -0.0042(4) -0.0056(3) -0.0086(3) F7B3 0.0411(12) 0.0336(11) 0.0248(10) -0.0109(9) -0.0113(9) -0.0016(9) F7B1 0.0362(12) 0.0454(13) 0.0282(11) -0.0094(10) 0.0053(9) -0.0076(10) F7A3 0.0490(14) 0.0438(14) 0.0679(16) 0.0127(12) -0.0397(13) -0.0267(11) F7B2 0.096(2) 0.0295(12) 0.0183(11) 0.0050(9) -0.0086(12) 0.0013(12) F7A2 0.0342(13) 0.0716(17) 0.0403(13) -0.0219(12) -0.0130(11) 0.0274(12) F8A2 0.0524(15) 0.0708(17) 0.0255(12) -0.0092(11) -0.0213(11) 0.0026(13) C1A 0.0183(15) 0.0127(14) 0.0180(15) -0.0049(11) -0.0040(12) 0.0020(12) C2B 0.0213(16) 0.0165(15) 0.0197(15) -0.0029(12) -0.0036(13) -0.0032(12) F8A3 0.0409(14) 0.091(2) 0.0594(17) 0.0291(15) -0.0344(13) -0.0269(14) C1B 0.0193(15) 0.0156(15) 0.0204(16) -0.0050(12) -0.0026(13) -0.0038(12) C2A 0.0222(17) 0.0212(16) 0.0208(16) -0.0048(13) -0.0071(13) -0.0026(13) F8A1 0.0788(19) 0.0467(15) 0.0597(16) -0.0203(13) -0.0459(15) 0.0313(14) C6B 0.0286(18) 0.0189(16) 0.0217(16) -0.0043(13) -0.0041(14) -0.0050(13) C3B 0.0229(16) 0.0176(16) 0.0253(17) -0.0086(13) -0.0038(13) -0.0040(13) C7A 0.0180(16) 0.0278(18) 0.0267(18) -0.0028(14) -0.0048(14) -0.0027(14) C3A 0.0246(17) 0.0226(17) 0.0186(16) -0.0051(13) -0.0072(13) 0.0014(13) C8B 0.0272(18) 0.0260(18) 0.0332(19) -0.0109(15) -0.0051(15) -0.0057(15) C6A 0.0188(15) 0.0174(16) 0.0213(16) -0.0045(13) -0.0060(13) -0.0018(12) C5B 0.037(2) 0.0182(17) 0.0264(18) 0.0002(14) -0.0076(16) -0.0040(15) C4B 0.0314(19) 0.0161(16) 0.0318(19) -0.0070(14) -0.0059(15) -0.0005(14) C5A 0.0215(17) 0.0284(19) 0.0256(18) 0.0000(14) -0.0049(14) -0.0083(14) C7B 0.041(2) 0.0204(17) 0.0206(17) -0.0013(14) -0.0053(16) 0.0000(15) C4A 0.0281(18) 0.0262(18) 0.0245(18) 0.0011(14) -0.0069(15) -0.0075(15) C8A 0.034(2) 0.034(2) 0.0245(18) -0.0031(15) -0.0117(16) -0.0025(17) F7A1 0.0244(10) 0.0380(12) 0.0254(10) 0.0001(9) -0.0111(8) -0.0042(9) _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 Cl1 2.0681(12) . ? P1 C1A 1.858(3) . ? P1 C1B 1.858(3) . ? F7B3 C7B 1.351(4) . ? F7B1 C7B 1.348(4) . ? F7A3 C7A 1.328(4) . ? F7B2 C7B 1.340(4) . ? F7A2 C7A 1.342(4) . ? F8A2 C8A 1.334(4) . ? C1A C2A 1.405(4) . ? C1A C6A 1.410(4) . ? C2B H2B 0.9500 . ? C2B C1B 1.392(4) . ? C2B C3B 1.395(4) . ? F8A3 C8A 1.332(4) . ? C1B C6B 1.407(4) . ? C2A H2A 0.9500 . ? C2A C3A 1.392(4) . ? F8A1 C8A 1.327(4) . ? C6B C5B 1.395(5) . ? C6B C7B 1.507(5) . ? C3B C8B 1.503(5) . ? C3B C4B 1.382(4) . ? C7A C6A 1.508(4) . ? C7A F7A1 1.343(4) . ? C3A C4A 1.380(5) . ? C3A C8A 1.511(5) . ? C8B F8B8 1.274(7) . ? C8B F8B9 1.365(7) . ? C8B F8B7 1.343(7) . ? C8B F8B1 1.336(5) . ? C8B F8B2 1.366(5) . ? C8B F8B3 1.357(5) . ? C8B F8B4 1.420(7) . ? C8B F8B5 1.339(8) . ? C8B F8B6 1.310(7) . ? C6A C5A 1.389(4) . ? C5B H5B 0.9500 . ? C5B C4B 1.390(5) . ? C4B H4B 0.9500 . ? C5A H5A 0.9500 . ? C5A C4A 1.386(5) . ? C4A H4A 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 F7B3 C7B C6B 112.2(3) . . ? F7B1 C7B F7B3 106.0(3) . . ? F7B1 C7B C6B 112.1(3) . . ? F7A3 C7A F7A2 106.9(3) . . ? F7A3 C7A C6A 112.4(3) . . ? F7A3 C7A F7A1 106.3(3) . . ? F7B2 C7B F7B3 106.2(3) . . ? F7B2 C7B F7B1 107.2(3) . . ? F7B2 C7B C6B 112.8(3) . . ? F7A2 C7A C6A 111.2(3) . . ? F7A2 C7A F7A1 105.2(3) . . ? F8A2 C8A C3A 112.2(3) . . ? C1A P1 Cl1 101.12(10) . . ? C1A C2A H2A 119.6 . . ? C1A C6A C7A 124.0(3) . . ? C2B C1B P1 121.6(2) . . ? C2B C1B C6B 118.2(3) . . ? C2B C3B C8B 119.2(3) . . ? F8A3 C8A F8A2 106.1(3) . . ? F8A3 C8A C3A 113.2(3) . . ? C1B P1 Cl1 97.26(10) . . ? C1B P1 C1A 101.61(13) . . ? C1B C2B H2B 119.6 . . ? C1B C2B C3B 120.9(3) . . ? C1B C6B C7B 121.2(3) . . ? C2A C1A P1 119.7(2) . . ? C2A C1A C6A 117.1(3) . . ? C2A C3A C8A 119.8(3) . . ? F8A1 C8A F8A2 105.9(3) . . ? F8A1 C8A F8A3 107.5(3) . . ? F8A1 C8A C3A 111.4(3) . . ? C6B C1B P1 120.1(2) . . ? C6B C5B H5B 120.0 . . ? C3B C2B H2B 119.6 . . ? C3B C4B C5B 119.8(3) . . ? C3B C4B H4B 120.1 . . ? C3A C2A C1A 120.9(3) . . ? C3A C2A H2A 119.6 . . ? C3A C4A C5A 118.6(3) . . ? C3A C4A H4A 120.7 . . ? C6A C1A P1 122.8(2) . . ? C6A C5A H5A 119.5 . . ? C5B C6B C1B 120.7(3) . . ? C5B C6B C7B 118.1(3) . . ? C5B C4B H4B 120.1 . . ? C4B C3B C2B 120.4(3) . . ? C4B C3B C8B 120.4(3) . . ? C4B C5B C6B 120.0(3) . . ? C4B C5B H5B 120.0 . . ? C5A C6A C1A 121.1(3) . . ? C5A C6A C7A 114.9(3) . . ? C5A C4A H4A 120.7 . . ? C4A C3A C2A 121.4(3) . . ? C4A C3A C8A 118.8(3) . . ? C4A C5A C6A 121.1(3) . . ? C4A C5A H5A 119.5 . . ? F8B8 C8B C3B 112.2(5) . . ? F8B8 C8B F8B9 109.5(6) . . ? F8B8 C8B F8B7 113.6(6) . . ? F8B8 C8B F8B1 85.7(5) . . ? F8B8 C8B F8B2 23.7(4) . . ? F8B8 C8B F8B3 123.2(5) . . ? F8B8 C8B F8B4 60.5(5) . . ? F8B8 C8B F8B5 40.4(5) . . ? F8B8 C8B F8B6 129.5(6) . . ? F8B9 C8B C3B 107.7(4) . . ? F8B9 C8B F8B2 88.5(4) . . ? F8B9 C8B F8B4 138.6(6) . . ? F8B7 C8B C3B 107.7(4) . . ? F8B7 C8B F8B9 105.9(5) . . ? F8B7 C8B F8B2 132.5(5) . . ? F8B7 C8B F8B3 83.4(4) . . ? F8B7 C8B F8B4 55.7(5) . . ? F8B1 C8B C3B 111.0(3) . . ? F8B1 C8B F8B9 128.5(5) . . ? F8B1 C8B F8B7 30.0(3) . . ? F8B1 C8B F8B2 107.8(4) . . ? F8B1 C8B F8B3 108.4(4) . . ? F8B1 C8B F8B4 25.9(3) . . ? F8B1 C8B F8B5 117.9(5) . . ? F8B2 C8B C3B 110.4(3) . . ? F8B2 C8B F8B4 83.5(4) . . ? F8B3 C8B C3B 112.7(3) . . ? F8B3 C8B F8B9 22.7(3) . . ? F8B3 C8B F8B2 106.4(3) . . ? F8B3 C8B F8B4 125.5(5) . . ? F8B4 C8B C3B 113.1(4) . . ? F8B5 C8B C3B 116.1(5) . . ? F8B5 C8B F8B9 70.3(5) . . ? F8B5 C8B F8B7 135.1(6) . . ? F8B5 C8B F8B2 18.2(4) . . ? F8B5 C8B F8B3 88.5(5) . . ? F8B5 C8B F8B4 96.6(5) . . ? F8B6 C8B C3B 117.6(4) . . ? F8B6 C8B F8B9 47.9(5) . . ? F8B6 C8B F8B7 58.1(5) . . ? F8B6 C8B F8B1 84.0(5) . . ? F8B6 C8B F8B2 121.9(5) . . ? F8B6 C8B F8B3 25.3(4) . . ? F8B6 C8B F8B4 104.6(5) . . ? F8B6 C8B F8B5 106.2(6) . . ? F7A1 C7A C6A 114.3(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 P1 C1A C2A C3A -173.3(2) . . . . ? P1 C1A C6A C7A -7.3(4) . . . . ? P1 C1A C6A C5A 173.2(2) . . . . ? P1 C1B C6B C5B 179.9(3) . . . . ? P1 C1B C6B C7B -0.1(4) . . . . ? Cl1 P1 C1A C2A -12.5(3) . . . . ? Cl1 P1 C1A C6A 175.2(2) . . . . ? Cl1 P1 C1B C2B -81.3(3) . . . . ? Cl1 P1 C1B C6B 98.5(3) . . . . ? F7A3 C7A C6A C1A 133.4(3) . . . . ? F7A3 C7A C6A C5A -47.1(4) . . . . ? F7A2 C7A C6A C1A -106.8(3) . . . . ? F7A2 C7A C6A C5A 72.8(4) . . . . ? C1A P1 C1B C2B 21.7(3) . . . . ? C1A P1 C1B C6B -158.5(3) . . . . ? C1A C2A C3A C4A 0.4(5) . . . . ? C1A C2A C3A C8A 177.1(3) . . . . ? C1A C6A C5A C4A -0.8(5) . . . . ? C2B C1B C6B C5B -0.3(5) . . . . ? C2B C1B C6B C7B 179.7(3) . . . . ? C2B C3B C8B F8B8 44.5(6) . . . . ? C2B C3B C8B F8B9 165.1(4) . . . . ? C2B C3B C8B F8B7 -81.2(5) . . . . ? C2B C3B C8B F8B1 -49.5(4) . . . . ? C2B C3B C8B F8B2 69.9(4) . . . . ? C2B C3B C8B F8B3 -171.3(3) . . . . ? C2B C3B C8B F8B4 -21.6(5) . . . . ? C2B C3B C8B F8B5 88.8(5) . . . . ? C2B C3B C8B F8B6 -143.8(5) . . . . ? C2B C3B C4B C5B -0.8(5) . . . . ? C1B P1 C1A C2A -112.4(3) . . . . ? C1B P1 C1A C6A 75.3(3) . . . . ? C1B C2B C3B C8B -179.8(3) . . . . ? C1B C2B C3B C4B -0.3(5) . . . . ? C1B C6B C5B C4B -0.8(5) . . . . ? C1B C6B C7B F7B3 63.1(4) . . . . ? C1B C6B C7B F7B1 -56.0(4) . . . . ? C1B C6B C7B F7B2 -177.0(3) . . . . ? C2A C1A C6A C7A -179.8(3) . . . . ? C2A C1A C6A C5A 0.7(4) . . . . ? C2A C3A C4A C5A -0.5(5) . . . . ? C2A C3A C8A F8A2 137.1(3) . . . . ? C2A C3A C8A F8A3 17.0(5) . . . . ? C2A C3A C8A F8A1 -104.3(4) . . . . ? C6B C5B C4B C3B 1.4(5) . . . . ? C3B C2B C1B P1 -179.3(2) . . . . ? C3B C2B C1B C6B 0.9(5) . . . . ? C7A C6A C5A C4A 179.7(3) . . . . ? C8B C3B C4B C5B 178.7(3) . . . . ? C6A C1A C2A C3A -0.5(4) . . . . ? C6A C5A C4A C3A 0.6(5) . . . . ? C5B C6B C7B F7B3 -116.9(3) . . . . ? C5B C6B C7B F7B1 124.0(3) . . . . ? C5B C6B C7B F7B2 3.0(5) . . . . ? C4B C3B C8B F8B8 -135.0(5) . . . . ? C4B C3B C8B F8B9 -14.4(5) . . . . ? C4B C3B C8B F8B7 99.3(5) . . . . ? C4B C3B C8B F8B1 131.0(4) . . . . ? C4B C3B C8B F8B2 -109.5(4) . . . . ? C4B C3B C8B F8B3 9.3(5) . . . . ? C4B C3B C8B F8B4 158.9(5) . . . . ? C4B C3B C8B F8B5 -90.7(5) . . . . ? C4B C3B C8B F8B6 36.7(6) . . . . ? C7B C6B C5B C4B 179.2(3) . . . . ? C4A C3A C8A F8A2 -46.1(4) . . . . ? C4A C3A C8A F8A3 -166.2(3) . . . . ? C4A C3A C8A F8A1 72.5(4) . . . . ? C8A C3A C4A C5A -177.2(3) . . . . ? F7A1 C7A C6A C1A 12.1(5) . . . . ? F7A1 C7A C6A C5A -168.4(3) . . . . ? # Attachment '- Ar2POH_cif.cif' data_s297 _database_code_depnum_ccdc_archive 'CCDC 795646' #TrackingRef '- Ar2POH_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H7 F12 O P' _chemical_formula_sum 'C16 H7 F12 O P' _chemical_formula_weight 474.19 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.1273(3) _cell_length_b 8.2646(2) _cell_length_c 25.3157(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3374.22(12) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7001 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 30.50 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8202 _exptl_absorpt_correction_T_max 0.9404 _exptl_absorpt_process_details 'SADABS,Sheldrick (1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker SMART CCD 6000' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41514 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 29.50 _reflns_number_total 4694 _reflns_number_gt 4336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELX-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^)+(0.0500P)^2^+3.5000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4694 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.071 _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 P1 P 0.02184(2) 0.26494(5) 0.187163(15) 0.01776(10) Uani 1 1 d D . . O1 O 0.01945(7) 0.08648(15) 0.19330(5) 0.0233(2) Uani 1 1 d . . . F1 F -0.01179(8) 0.61804(14) 0.18798(4) 0.0310(2) Uani 1 1 d . . . F2 F -0.04559(8) 0.76791(13) 0.12237(5) 0.0349(3) Uani 1 1 d . . . F3 F 0.07515(7) 0.65757(15) 0.12538(5) 0.0370(3) Uani 1 1 d . . . F4 F -0.09238(13) -0.05170(15) 0.02802(7) 0.0655(5) Uani 1 1 d . . . F5 F -0.10815(13) 0.11065(18) -0.03660(5) 0.0633(5) Uani 1 1 d . . . F6 F -0.20692(11) 0.0762(2) 0.01711(8) 0.0710(5) Uani 1 1 d . . . F7 F 0.12939(7) 0.14105(13) 0.10496(4) 0.0270(2) Uani 1 1 d . . . F8 F 0.15660(8) 0.37340(14) 0.07120(4) 0.0335(3) Uani 1 1 d . . . F9 F 0.25530(7) 0.20487(15) 0.08753(4) 0.0341(3) Uani 1 1 d . . . F10 F 0.18535(7) 0.69677(13) 0.31457(4) 0.0298(2) Uani 1 1 d . . . F11 F 0.19817(8) 0.46311(13) 0.35071(4) 0.0328(3) Uani 1 1 d . . . F12 F 0.30658(7) 0.58982(17) 0.32265(5) 0.0391(3) Uani 1 1 d . . . C1 C -0.02468(9) 0.32883(19) 0.12483(6) 0.0179(3) Uani 1 1 d . . . C2 C -0.03745(9) 0.48732(19) 0.10637(6) 0.0186(3) Uani 1 1 d . . . C3 C -0.07831(11) 0.5139(2) 0.05853(7) 0.0238(3) Uani 1 1 d . . . C4 C -0.10677(11) 0.3843(2) 0.02888(7) 0.0261(3) Uani 1 1 d . . . C5 C -0.09358(11) 0.2279(2) 0.04675(7) 0.0240(3) Uani 1 1 d . . . C6 C -0.05309(10) 0.19949(19) 0.09442(6) 0.0211(3) Uani 1 1 d . . . C7 C -0.00534(10) 0.6336(2) 0.13525(7) 0.0223(3) Uani 1 1 d . . . C8 C -0.12499(15) 0.0888(2) 0.01421(8) 0.0368(5) Uani 1 1 d . . . C9 C 0.12498(9) 0.35043(18) 0.19543(6) 0.0170(3) Uani 1 1 d . . . C10 C 0.19289(9) 0.33452(18) 0.16070(6) 0.0182(3) Uani 1 1 d . . . C11 C 0.27105(10) 0.3893(2) 0.17529(7) 0.0214(3) Uani 1 1 d . . . C12 C 0.28377(10) 0.46108(19) 0.22430(7) 0.0219(3) Uani 1 1 d . . . C13 C 0.21720(10) 0.47809(18) 0.25843(6) 0.0197(3) Uani 1 1 d . . . C14 C 0.13824(9) 0.42354(18) 0.24429(6) 0.0183(3) Uani 1 1 d . . . C15 C 0.18373(10) 0.2630(2) 0.10619(6) 0.0224(3) Uani 1 1 d . . . C16 C 0.22753(10) 0.5559(2) 0.31167(7) 0.0240(3) Uani 1 1 d . . . H1P H -0.0194(10) 0.350(2) 0.2237(6) 0.012(4) Uiso 1 1 d D . . H3 H -0.0873(14) 0.621(3) 0.0477(9) 0.027(5) Uiso 1 1 d . . . H4 H -0.1369(15) 0.409(3) -0.0042(10) 0.034(6) Uiso 1 1 d . . . H6 H -0.0452(14) 0.092(3) 0.1071(9) 0.025(5) Uiso 1 1 d . . . H11 H 0.3149(16) 0.377(3) 0.1525(10) 0.033(6) Uiso 1 1 d . . . H12 H 0.3369(14) 0.494(3) 0.2332(9) 0.028(6) Uiso 1 1 d . . . H14 H 0.0941(13) 0.431(3) 0.2687(8) 0.020(5) Uiso 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 P1 0.01681(18) 0.02057(19) 0.01591(17) 0.00246(13) -0.00186(12) -0.00181(13) O1 0.0254(6) 0.0227(6) 0.0218(5) 0.0050(4) -0.0044(4) -0.0042(4) F1 0.0425(6) 0.0275(5) 0.0228(5) -0.0036(4) -0.0032(4) -0.0004(5) F2 0.0469(7) 0.0181(5) 0.0397(6) -0.0011(4) -0.0123(5) 0.0065(5) F3 0.0266(5) 0.0327(6) 0.0516(7) -0.0073(5) 0.0041(5) -0.0099(4) F4 0.1132(14) 0.0210(6) 0.0622(9) -0.0028(6) -0.0552(10) 0.0022(7) F5 0.1228(15) 0.0376(7) 0.0295(6) -0.0082(6) -0.0213(8) -0.0033(8) F6 0.0578(10) 0.0648(11) 0.0904(13) -0.0140(9) -0.0295(9) -0.0261(8) F7 0.0308(5) 0.0257(5) 0.0245(5) -0.0053(4) -0.0007(4) 0.0001(4) F8 0.0484(7) 0.0325(6) 0.0194(5) 0.0073(4) -0.0020(4) 0.0072(5) F9 0.0287(5) 0.0458(7) 0.0279(5) -0.0076(5) 0.0081(4) 0.0088(5) F10 0.0355(6) 0.0203(5) 0.0334(5) -0.0050(4) -0.0008(4) -0.0004(4) F11 0.0502(7) 0.0268(5) 0.0213(5) 0.0012(4) -0.0028(4) -0.0037(5) F12 0.0260(5) 0.0501(7) 0.0412(6) -0.0150(6) -0.0113(5) -0.0044(5) C1 0.0169(6) 0.0204(7) 0.0163(6) 0.0016(5) -0.0011(5) 0.0002(5) C2 0.0183(6) 0.0188(6) 0.0187(6) -0.0001(5) -0.0003(5) 0.0007(5) C3 0.0283(8) 0.0205(7) 0.0226(7) 0.0032(6) -0.0046(6) 0.0030(6) C4 0.0323(8) 0.0254(8) 0.0204(7) 0.0029(6) -0.0089(6) 0.0013(7) C5 0.0285(8) 0.0221(7) 0.0214(7) -0.0001(6) -0.0073(6) -0.0009(6) C6 0.0236(7) 0.0194(7) 0.0202(7) 0.0022(5) -0.0038(6) -0.0008(6) C7 0.0232(7) 0.0198(7) 0.0240(7) -0.0006(6) -0.0013(6) 0.0002(6) C8 0.0529(12) 0.0264(8) 0.0310(9) -0.0005(7) -0.0217(9) -0.0035(8) C9 0.0161(6) 0.0169(6) 0.0181(6) 0.0019(5) -0.0009(5) 0.0005(5) C10 0.0199(7) 0.0164(6) 0.0181(6) 0.0023(5) 0.0015(5) 0.0026(5) C11 0.0179(7) 0.0216(7) 0.0246(7) 0.0045(6) 0.0033(5) 0.0012(6) C12 0.0172(6) 0.0198(7) 0.0287(8) 0.0041(6) -0.0016(6) -0.0017(5) C13 0.0206(7) 0.0168(6) 0.0216(7) 0.0009(5) -0.0031(5) -0.0013(5) C14 0.0174(6) 0.0182(6) 0.0192(6) 0.0007(5) -0.0001(5) 0.0012(5) C15 0.0241(7) 0.0232(7) 0.0199(7) 0.0014(6) 0.0026(6) 0.0038(6) C16 0.0236(7) 0.0224(7) 0.0260(8) -0.0020(6) -0.0043(6) -0.0027(6) _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 1.4835(13) . y P1 C9 1.8192(15) . y P1 C1 1.8252(15) . y P1 H1P 1.339(5) . ? F1 C7 1.3453(19) . y F2 C7 1.3266(19) . y F3 C7 1.337(2) . y F4 C8 1.322(2) . y F5 C8 1.327(3) . y F6 C8 1.327(3) . y F7 C15 1.336(2) . y F8 C15 1.3445(19) . y F9 C15 1.3366(19) . y F10 C16 1.350(2) . y F11 C16 1.338(2) . y F12 C16 1.3345(19) . y C1 C6 1.395(2) . y C1 C2 1.406(2) . y C2 C3 1.396(2) . y C2 C7 1.504(2) . y C3 C4 1.386(2) . y C3 H3 0.93(2) . ? C4 C5 1.386(2) . y C4 H4 0.99(2) . ? C5 C6 1.392(2) . y C5 C8 1.502(2) . y C6 H6 0.95(2) . ? C9 C14 1.393(2) . y C9 C10 1.411(2) . y C10 C11 1.389(2) . y C10 C15 1.508(2) . y C11 C12 1.390(2) . y C11 H11 0.92(3) . ? C12 C13 1.385(2) . y C12 H12 0.93(2) . ? C13 C14 1.397(2) . y C13 C16 1.503(2) . y C14 H14 0.95(2) . ? 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 C9 113.44(7) . . y O1 P1 C1 111.56(7) . . y C9 P1 C1 111.28(7) . . y O1 P1 H1P 116.0(8) . . ? C9 P1 H1P 99.8(8) . . ? C1 P1 H1P 103.9(8) . . ? C6 C1 C2 118.84(14) . . y C6 C1 P1 112.99(11) . . y C2 C1 P1 128.11(12) . . y C3 C2 C1 120.29(14) . . y C3 C2 C7 117.21(14) . . y C1 C2 C7 122.45(14) . . y C4 C3 C2 120.27(15) . . y C4 C3 H3 121.3(14) . . ? C2 C3 H3 118.4(14) . . ? C5 C4 C3 119.57(15) . . y C5 C4 H4 123.0(14) . . ? C3 C4 H4 117.5(14) . . ? C4 C5 C6 120.80(15) . . y C4 C5 C8 118.87(15) . . y C6 C5 C8 120.32(15) . . y C5 C6 C1 120.23(15) . . y C5 C6 H6 120.8(14) . . ? C1 C6 H6 119.0(14) . . ? F2 C7 F3 107.76(14) . . y F2 C7 F1 106.61(14) . . y F3 C7 F1 105.94(14) . . y F2 C7 C2 112.62(14) . . y F3 C7 C2 111.26(14) . . y F1 C7 C2 112.27(14) . . y F4 C8 F5 107.1(2) . . y F4 C8 F6 108.2(2) . . y F5 C8 F6 105.54(18) . . y F4 C8 C5 113.14(15) . . y F5 C8 C5 111.02(17) . . y F6 C8 C5 111.45(19) . . y C14 C9 C10 118.34(14) . . y C14 C9 P1 114.27(11) . . y C10 C9 P1 127.00(12) . . y C11 C10 C9 120.54(14) . . y C11 C10 C15 117.37(14) . . y C9 C10 C15 122.06(14) . . y C10 C11 C12 120.67(14) . . y C10 C11 H11 119.6(15) . . ? C12 C11 H11 119.7(15) . . ? C13 C12 C11 119.05(14) . . y C13 C12 H12 122.4(14) . . ? C11 C12 H12 118.5(14) . . ? C12 C13 C14 120.91(14) . . y C12 C13 C16 121.13(14) . . y C14 C13 C16 117.96(14) . . y C9 C14 C13 120.48(14) . . y C9 C14 H14 119.7(13) . . ? C13 C14 H14 119.8(13) . . ? F7 C15 F9 106.67(13) . . y F7 C15 F8 106.45(14) . . y F9 C15 F8 106.99(13) . . y F7 C15 C10 112.39(13) . . y F9 C15 C10 112.31(14) . . y F8 C15 C10 111.64(13) . . y F12 C16 F11 107.73(14) . . y F12 C16 F10 106.79(14) . . y F11 C16 F10 106.01(14) . . y F12 C16 C13 112.50(14) . . y F11 C16 C13 112.21(13) . . y F10 C16 C13 111.22(13) . . y 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 C2 C1 P1 O1 176.55(13) . . . . ? C2 C1 P1 C9 -55.65(16) . . . . ? C6 C1 P1 O1 -0.51(14) . . . . ? C6 C1 P1 C9 127.30(12) . . . . ? C1 P1 C9 C10 -56.45(15) . . . . ? O1 P1 C9 C10 70.33(15) . . . . ? C1 P1 C9 C14 130.89(11) . . . . ? O1 P1 C9 C14 -102.33(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A P1 H1P O1 1.339(5) 2.868(10) 4.0820(12) 149.8(11) 3 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.607 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.066 # Attachment '- Ar2POOH_cif.cif' data_ARPOOH _database_code_depnum_ccdc_archive 'CCDC 795647' _audit_creation_method SHELXL-97 _chemical_formula_moiety '2(C16 H7 F11.99997 O2 P)' _chemical_formula_sum 'C32 H14 F24 O4 P2' _chemical_formula_weight 980.37 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ? 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' _space_group_IT_number 14 _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 99.4550(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 12.8361(6) _cell_length_b 16.8192(8) _cell_length_c 8.1211(4) _cell_measurement_reflns_used 9304 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 28.265 _cell_measurement_theta_min 2.422 _cell_volume 1729.47(14) _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.875796 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0444 before and 0.0250 after correction. The Ratio of minimum to maximum transmission is 0.875796. The \l/2 correction factor is 0.0000 ; _exptl_crystal_F_000 968 _exptl_crystal_colour ? _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.883 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.424 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.0 _diffrn_detector_type 'Bruker SMART CCD 1K area detector' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'BRUKER SMART CCD 1000' _diffrn_measurement_method 'phi and omega scans' _diffrn_orient_matrix_UB_11 -0.009504 _diffrn_orient_matrix_UB_12 -0.059228 _diffrn_orient_matrix_UB_13 -0.000996 _diffrn_orient_matrix_UB_21 0.020488 _diffrn_orient_matrix_UB_22 -0.000777 _diffrn_orient_matrix_UB_23 0.078875 _diffrn_orient_matrix_UB_31 -0.122421 _diffrn_orient_matrix_UB_32 0.004411 _diffrn_orient_matrix_UB_33 -4.5e-05 _diffrn_radiation_monochromator Parallel,graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 16428 _diffrn_reflns_theta_full 28.27 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_min 1.61 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3592 _reflns_number_total 4265 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.049 (Bruker, 1999)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.702 _refine_diff_density_min -0.801 _refine_diff_density_rms 0.068 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0461 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 4265 _refine_ls_number_restraints 54 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1120 _refine_ls_wR_factor_ref 0.1180 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+2.1253P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.62904(4) 0.52008(3) 0.66891(7) 0.01861(14) Uani 1 1 d . . . O1 O 0.62569(12) 0.52196(10) 0.4830(2) 0.0256(3) Uani 1 1 d . . . F1B F 0.64086(11) 0.50772(10) 1.04119(18) 0.0349(4) Uani 1 1 d . . . F3A F 0.82598(12) 0.74339(9) 0.6288(2) 0.0356(4) Uani 1 1 d . . . F5A F 0.37209(13) 0.67938(9) 1.01968(19) 0.0352(4) Uani 1 1 d . . . O2 O 0.53944(13) 0.47073(9) 0.7231(2) 0.0250(3) Uani 1 1 d . . . F2A F 0.79341(11) 0.62109(9) 0.5692(2) 0.0345(3) Uani 1 1 d . . . F1A F 0.86303(12) 0.65366(11) 0.8184(2) 0.0425(4) Uani 1 1 d . . . F3B F 0.77520(15) 0.58345(10) 1.0886(2) 0.0470(4) Uani 1 1 d . . . C1B C 0.75221(16) 0.47394(12) 0.7643(3) 0.0193(4) Uani 1 1 d . . . F2B F 0.77457(16) 0.47248(12) 1.21808(19) 0.0539(5) Uani 1 1 d . . . C1A C 0.61376(16) 0.62072(12) 0.7432(3) 0.0197(4) Uani 1 1 d . . . F4A F 0.36680(15) 0.79955(9) 0.9280(2) 0.0465(5) Uani 1 1 d . . . C6A C 0.68288(17) 0.68546(13) 0.7350(3) 0.0224(4) Uani 1 1 d . . . C2B C 0.80570(17) 0.43731(13) 0.6489(3) 0.0230(4) Uani 1 1 d . . . H2B H 0.7788 0.4415 0.5330 0.028 Uiso 1 1 calc R . . C6B C 0.79446(17) 0.46726(13) 0.9352(3) 0.0212(4) Uani 1 1 d . . . C3B C 0.89784(18) 0.39473(15) 0.7011(3) 0.0274(5) Uani 1 1 d . A . C2A C 0.51747(17) 0.63554(13) 0.7958(3) 0.0222(4) Uani 1 1 d . . . H2A H 0.4706 0.5927 0.8051 0.027 Uiso 1 1 calc R . . C7B C 0.74580(19) 0.50700(14) 1.0710(3) 0.0257(5) Uani 1 1 d . . . C4B C 0.93899(19) 0.38813(15) 0.8688(3) 0.0296(5) Uani 1 1 d . . . H4B H 1.0021 0.3589 0.9039 0.035 Uiso 1 1 calc R . . F6A F 0.30364(12) 0.70388(12) 0.7662(2) 0.0455(4) Uani 1 1 d . . . C3A C 0.48900(18) 0.71261(14) 0.8350(3) 0.0241(4) Uani 1 1 d . . . C7A C 0.79112(18) 0.67585(14) 0.6872(3) 0.0257(5) Uani 1 1 d . . . C5B C 0.88703(19) 0.42466(15) 0.9855(3) 0.0271(5) Uani 1 1 d . . . H5B H 0.9150 0.4205 1.1009 0.033 Uiso 1 1 calc R . . C4A C 0.5565(2) 0.77548(14) 0.8243(3) 0.0280(5) Uani 1 1 d . . . H4A H 0.5366 0.8279 0.8500 0.034 Uiso 1 1 calc R . . C5A C 0.6536(2) 0.76178(14) 0.7758(3) 0.0272(5) Uani 1 1 d . . . H5A H 0.7007 0.8049 0.7704 0.033 Uiso 1 1 calc R . . C8A C 0.3830(2) 0.72424(15) 0.8870(3) 0.0295(5) Uani 1 1 d . . . C8B C 0.9513(2) 0.35482(19) 0.5725(4) 0.0443(7) Uani 1 1 d D . . F5B F 1.0340(6) 0.3135(5) 0.6149(12) 0.0522(7) Uani 0.33 1 d PD A 2 F4B F 0.9827(5) 0.4175(4) 0.4677(8) 0.0522(7) Uani 0.33 1 d PD A 2 F6B F 0.8846(5) 0.3189(5) 0.4491(7) 0.0522(7) Uani 0.33 1 d PD A 2 F12B F 0.8972(5) 0.2886(4) 0.5107(8) 0.0522(7) Uani 0.33 1 d PD A 1 F10B F 0.9573(6) 0.4005(4) 0.4356(7) 0.0522(7) Uani 0.33 1 d PD A 1 F11B F 1.0499(7) 0.3324(5) 0.6292(14) 0.0522(7) Uani 0.33 1 d PD A 1 F8B F 1.0562(6) 0.3558(5) 0.6300(11) 0.0522(7) Uani 0.33 1 d PD A 3 F7B F 0.9207(5) 0.3717(5) 0.4244(7) 0.0522(7) Uani 0.33 1 d PD A 3 F9B F 0.9345(5) 0.2716(3) 0.5875(7) 0.0522(7) Uani 0.33 1 d PD A 3 H2 H 0.468(4) 0.472(3) 0.632(7) 0.106(17) Uiso 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 P1 0.0154(2) 0.0189(3) 0.0212(3) -0.0005(2) 0.00202(19) 0.00127(19) O1 0.0212(8) 0.0309(9) 0.0238(8) -0.0009(7) 0.0012(6) 0.0017(6) F1B 0.0272(7) 0.0489(9) 0.0302(8) -0.0033(7) 0.0091(6) 0.0043(6) F3A 0.0296(8) 0.0285(7) 0.0501(9) 0.0062(7) 0.0109(7) -0.0090(6) F5A 0.0409(9) 0.0340(8) 0.0341(8) 0.0058(6) 0.0160(7) 0.0061(6) O2 0.0213(8) 0.0218(8) 0.0319(9) 0.0013(6) 0.0045(6) -0.0003(6) F2A 0.0275(7) 0.0322(8) 0.0470(9) -0.0057(7) 0.0156(6) -0.0045(6) F1A 0.0234(7) 0.0614(11) 0.0402(9) 0.0146(8) -0.0025(6) 0.0044(7) F3B 0.0538(10) 0.0365(9) 0.0561(11) -0.0215(8) 0.0250(9) -0.0112(8) C1B 0.0167(9) 0.0181(9) 0.0225(10) -0.0008(8) 0.0015(7) -0.0004(7) F2B 0.0675(12) 0.0750(13) 0.0207(7) 0.0120(8) 0.0119(7) 0.0382(10) C1A 0.0197(10) 0.0196(10) 0.0193(10) 0.0015(8) 0.0014(7) 0.0017(8) F4A 0.0577(11) 0.0282(8) 0.0614(11) 0.0047(7) 0.0330(9) 0.0175(7) C6A 0.0208(10) 0.0229(10) 0.0226(10) 0.0035(8) 0.0006(8) -0.0008(8) C2B 0.0198(10) 0.0265(11) 0.0223(10) -0.0019(8) 0.0018(8) 0.0023(8) C6B 0.0222(10) 0.0199(10) 0.0217(10) 0.0007(8) 0.0045(8) 0.0002(8) C3B 0.0229(11) 0.0301(12) 0.0295(12) -0.0011(10) 0.0049(9) 0.0067(9) C2A 0.0222(10) 0.0202(10) 0.0241(11) 0.0012(8) 0.0035(8) 0.0020(8) C7B 0.0270(11) 0.0285(11) 0.0213(11) 0.0009(9) 0.0035(8) 0.0041(9) C4B 0.0221(11) 0.0330(12) 0.0327(12) 0.0033(10) 0.0020(9) 0.0089(9) F6A 0.0247(8) 0.0756(13) 0.0366(9) -0.0024(8) 0.0062(6) 0.0096(8) C3A 0.0265(11) 0.0233(10) 0.0225(11) 0.0006(8) 0.0041(8) 0.0051(9) C7A 0.0210(10) 0.0258(11) 0.0294(12) 0.0047(9) 0.0012(9) -0.0033(9) C5B 0.0272(11) 0.0289(11) 0.0238(11) 0.0031(9) 0.0001(9) 0.0047(9) C4A 0.0369(13) 0.0193(10) 0.0274(12) -0.0005(9) 0.0039(10) 0.0044(9) C5A 0.0305(12) 0.0210(11) 0.0289(12) 0.0013(9) 0.0016(9) -0.0033(9) C8A 0.0337(13) 0.0265(11) 0.0297(12) 0.0017(9) 0.0093(10) 0.0091(10) C8B 0.0371(15) 0.0598(19) 0.0359(15) -0.0086(13) 0.0055(11) 0.0238(14) F5B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F4B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F6B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F12B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F10B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F11B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F8B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F7B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) F9B 0.0546(13) 0.0669(19) 0.0358(10) -0.0083(12) 0.0092(10) 0.0291(12) _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 1.5034(17) . ? P1 O2 1.5401(17) . ? P1 C1B 1.816(2) . ? P1 C1A 1.818(2) . ? F1B C7B 1.329(3) . ? F3A C7A 1.336(3) . ? F5A C8A 1.341(3) . ? O2 H2 1.08(5) . ? F2A C7A 1.333(3) . ? F1A C7A 1.343(3) . ? F3B C7B 1.341(3) . ? C1B C2B 1.393(3) . ? C1B C6B 1.409(3) . ? F2B C7B 1.325(3) . ? C1A C6A 1.413(3) . ? C1A C2A 1.395(3) . ? F4A C8A 1.335(3) . ? C6A C7A 1.511(3) . ? C6A C5A 1.393(3) . ? C2B H2B 0.9500 . ? C2B C3B 1.388(3) . ? C6B C7B 1.510(3) . ? C6B C5B 1.390(3) . ? C3B C4B 1.382(3) . ? C3B C8B 1.499(3) . ? C2A H2A 0.9500 . ? C2A C3A 1.398(3) . ? C4B H4B 0.9500 . ? C4B C5B 1.388(3) . ? F6A C8A 1.337(3) . ? C3A C4A 1.378(3) . ? C3A C8A 1.503(3) . ? C5B H5B 0.9500 . ? C4A H4A 0.9500 . ? C4A C5A 1.388(4) . ? C5A H5A 0.9500 . ? C8B F5B 1.268(8) . ? C8B F4B 1.453(7) . ? C8B F6B 1.349(6) . ? C8B F12B 1.364(7) . ? C8B F10B 1.363(7) . ? C8B F11B 1.328(8) . ? C8B F8B 1.350(8) . ? C8B F7B 1.235(6) . ? C8B F9B 1.424(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 P1 O2 H2 113(3) . . ? O1 P1 O2 113.49(10) . . ? O1 P1 C1B 108.45(10) . . ? O1 P1 C1A 109.07(10) . . ? F1B C7B F3B 105.65(19) . . ? F1B C7B C6B 113.54(19) . . ? F3A C7A F1A 106.93(19) . . ? F3A C7A C6A 112.06(19) . . ? F5A C8A C3A 111.8(2) . . ? O2 P1 C1B 106.65(10) . . ? O2 P1 C1A 106.30(9) . . ? F2A C7A F3A 106.52(19) . . ? F2A C7A F1A 106.5(2) . . ? F2A C7A C6A 112.84(19) . . ? F1A C7A C6A 111.53(19) . . ? F3B C7B C6B 111.06(19) . . ? C1B P1 C1A 112.96(10) . . ? C1B C2B H2B 119.6 . . ? C1B C6B C7B 123.08(19) . . ? F2B C7B F1B 107.0(2) . . ? F2B C7B F3B 107.0(2) . . ? F2B C7B C6B 112.16(19) . . ? C1A C6A C7A 122.7(2) . . ? C1A C2A H2A 119.6 . . ? C1A C2A C3A 120.9(2) . . ? F4A C8A F5A 107.0(2) . . ? F4A C8A F6A 107.2(2) . . ? F4A C8A C3A 112.2(2) . . ? C6A C1A P1 126.79(17) . . ? C6A C5A H5A 119.6 . . ? C2B C1B P1 113.12(16) . . ? C2B C1B C6B 118.35(19) . . ? C2B C3B C8B 118.9(2) . . ? C6B C1B P1 128.41(16) . . ? C6B C5B H5B 119.6 . . ? C3B C2B C1B 120.8(2) . . ? C3B C2B H2B 119.6 . . ? C3B C4B H4B 120.4 . . ? C3B C4B C5B 119.2(2) . . ? C2A C1A P1 114.66(16) . . ? C2A C1A C6A 118.1(2) . . ? C2A C3A C8A 117.9(2) . . ? C4B C3B C2B 120.7(2) . . ? C4B C3B C8B 120.4(2) . . ? C4B C5B C6B 120.7(2) . . ? C4B C5B H5B 119.6 . . ? F6A C8A F5A 106.2(2) . . ? F6A C8A C3A 112.1(2) . . ? C3A C2A H2A 119.6 . . ? C3A C4A H4A 120.2 . . ? C3A C4A C5A 119.6(2) . . ? C5B C6B C1B 120.2(2) . . ? C5B C6B C7B 116.7(2) . . ? C5B C4B H4B 120.4 . . ? C4A C3A C2A 120.4(2) . . ? C4A C3A C8A 121.7(2) . . ? C4A C5A C6A 120.7(2) . . ? C4A C5A H5A 119.6 . . ? C5A C6A C1A 120.2(2) . . ? C5A C6A C7A 117.1(2) . . ? C5A C4A H4A 120.2 . . ? F5B C8B C3B 121.0(5) . . ? F5B C8B F4B 104.8(6) . . ? F5B C8B F6B 110.9(5) . . ? F5B C8B F12B 90.3(5) . . ? F5B C8B F10B 111.9(6) . . ? F5B C8B F11B 16.8(6) . . ? F5B C8B F8B 33.9(4) . . ? F5B C8B F9B 64.6(5) . . ? F4B C8B C3B 106.6(3) . . ? F6B C8B C3B 114.3(3) . . ? F6B C8B F4B 95.3(4) . . ? F6B C8B F12B 30.5(3) . . ? F6B C8B F10B 76.1(5) . . ? F6B C8B F8B 137.5(4) . . ? F6B C8B F9B 62.4(4) . . ? F12B C8B C3B 111.0(3) . . ? F12B C8B F4B 123.4(4) . . ? F12B C8B F9B 32.2(3) . . ? F10B C8B C3B 114.2(4) . . ? F10B C8B F4B 19.2(4) . . ? F10B C8B F12B 104.7(4) . . ? F10B C8B F9B 130.8(4) . . ? F11B C8B C3B 113.8(5) . . ? F11B C8B F4B 94.0(6) . . ? F11B C8B F6B 125.6(5) . . ? F11B C8B F12B 107.1(5) . . ? F11B C8B F10B 105.3(7) . . ? F11B C8B F8B 17.2(6) . . ? F11B C8B F9B 80.8(5) . . ? F8B C8B C3B 107.4(4) . . ? F8B C8B F4B 80.6(5) . . ? F8B C8B F12B 123.7(5) . . ? F8B C8B F10B 95.1(5) . . ? F8B C8B F9B 98.0(5) . . ? F7B C8B C3B 117.8(3) . . ? F7B C8B F5B 120.5(6) . . ? F7B C8B F4B 48.5(4) . . ? F7B C8B F6B 47.0(4) . . ? F7B C8B F12B 76.6(5) . . ? F7B C8B F10B 29.4(4) . . ? F7B C8B F11B 122.4(7) . . ? F7B C8B F8B 118.2(6) . . ? F7B C8B F9B 106.3(5) . . ? F9B C8B C3B 106.7(3) . . ? F9B C8B F4B 145.4(4) . . ? 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 P1 C1B C2B C3B -175.84(19) . . . . ? P1 C1B C6B C7B -6.7(3) . . . . ? P1 C1B C6B C5B 175.44(18) . . . . ? P1 C1A C6A C7A -10.6(3) . . . . ? P1 C1A C6A C5A 171.06(17) . . . . ? P1 C1A C2A C3A -171.46(17) . . . . ? O1 P1 C1B C2B -11.62(19) . . . . ? O1 P1 C1B C6B 172.46(19) . . . . ? O1 P1 C1A C6A -62.9(2) . . . . ? O1 P1 C1A C2A 109.50(17) . . . . ? O2 P1 C1B C2B 110.95(17) . . . . ? O2 P1 C1B C6B -65.0(2) . . . . ? O2 P1 C1A C6A 174.37(19) . . . . ? O2 P1 C1A C2A -13.21(19) . . . . ? C1B P1 C1A C6A 57.8(2) . . . . ? C1B P1 C1A C2A -129.83(17) . . . . ? C1B C2B C3B C4B -0.4(4) . . . . ? C1B C2B C3B C8B 178.7(2) . . . . ? C1B C6B C7B F1B 37.1(3) . . . . ? C1B C6B C7B F3B -81.8(3) . . . . ? C1B C6B C7B F2B 158.5(2) . . . . ? C1B C6B C5B C4B -0.1(4) . . . . ? C1A P1 C1B C2B -132.64(16) . . . . ? C1A P1 C1B C6B 51.4(2) . . . . ? C1A C6A C7A F3A 157.1(2) . . . . ? C1A C6A C7A F2A 36.9(3) . . . . ? C1A C6A C7A F1A -83.0(3) . . . . ? C1A C6A C5A C4A -0.3(3) . . . . ? C1A C2A C3A C4A -0.8(3) . . . . ? C1A C2A C3A C8A 178.6(2) . . . . ? C6A C1A C2A C3A 1.7(3) . . . . ? C2B C1B C6B C7B 177.6(2) . . . . ? C2B C1B C6B C5B -0.3(3) . . . . ? C2B C3B C4B C5B 0.0(4) . . . . ? C2B C3B C8B F5B -178.1(6) . . . . ? C2B C3B C8B F4B 62.5(4) . . . . ? C2B C3B C8B F6B -41.4(5) . . . . ? C2B C3B C8B F12B -74.3(4) . . . . ? C2B C3B C8B F10B 43.7(5) . . . . ? C2B C3B C8B F11B 164.7(5) . . . . ? C2B C3B C8B F8B 147.7(4) . . . . ? C2B C3B C8B F7B 11.2(6) . . . . ? C2B C3B C8B F9B -108.1(4) . . . . ? C6B C1B C2B C3B 0.5(3) . . . . ? C3B C4B C5B C6B 0.2(4) . . . . ? C2A C1A C6A C7A 177.2(2) . . . . ? C2A C1A C6A C5A -1.1(3) . . . . ? C2A C3A C4A C5A -0.6(4) . . . . ? C2A C3A C8A F5A 57.1(3) . . . . ? C2A C3A C8A F4A 177.3(2) . . . . ? C2A C3A C8A F6A -62.0(3) . . . . ? C7B C6B C5B C4B -178.1(2) . . . . ? C4B C3B C8B F5B 1.0(7) . . . . ? C4B C3B C8B F4B -118.4(4) . . . . ? C4B C3B C8B F6B 137.7(5) . . . . ? C4B C3B C8B F12B 104.7(4) . . . . ? C4B C3B C8B F10B -137.2(4) . . . . ? C4B C3B C8B F11B -16.2(6) . . . . ? C4B C3B C8B F8B -33.3(5) . . . . ? C4B C3B C8B F7B -169.8(5) . . . . ? C4B C3B C8B F9B 70.9(4) . . . . ? C3A C4A C5A C6A 1.2(4) . . . . ? C7A C6A C5A C4A -178.7(2) . . . . ? C5B C6B C7B F1B -145.0(2) . . . . ? C5B C6B C7B F3B 96.2(2) . . . . ? C5B C6B C7B F2B -23.5(3) . . . . ? C4A C3A C8A F5A -123.5(2) . . . . ? C4A C3A C8A F4A -3.3(3) . . . . ? C4A C3A C8A F6A 117.4(3) . . . . ? C5A C6A C7A F3A -24.5(3) . . . . ? C5A C6A C7A F2A -144.8(2) . . . . ? C5A C6A C7A F1A 95.3(2) . . . . ? C8A C3A C4A C5A 180.0(2) . . . . ? C8B C3B C4B C5B -179.0(3) . . . . ? # Attachment '- Ar3P_cif.cif' data_ar3p _database_code_depnum_ccdc_archive 'CCDC 795648' #TrackingRef '- Ar3P_cif.cif' _audit_creation_date 2010-09-29 _audit_creation_method ; Olex2 1.1-beta (compiled 2010.09.10 svn.r1414, GUI svn.r3225) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H9 F18 P' _chemical_formula_sum 'C24 H9 F18 P' _chemical_formula_weight 670.28 _chemical_melting_point ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _cell_length_a 9.9017(6) _cell_length_b 14.8952(9) _cell_length_c 18.3713(11) _cell_angle_alpha 100.3820(10) _cell_angle_beta 93.6440(10) _cell_angle_gamma 108.8960(10) _cell_volume 2499.8(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7221 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.35 _cell_measurement_theta_min 2.33 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.82357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0416 before and 0.0305 after correction. The Ratio of minimum to maximum transmission is 0.823570. The \l/2 correction factor is 0.0000 ; _exptl_crystal_colour colourless _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 1320 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w. The crystal to detector distance was 4.424 cm. ; _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8 _diffrn_detector_type 'Bruker SMART CCD 1K area detector' _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_orient_matrix_UB_11 -0.006652 _diffrn_orient_matrix_UB_12 -0.069471 _diffrn_orient_matrix_UB_13 -0.008974 _diffrn_orient_matrix_UB_21 0.029979 _diffrn_orient_matrix_UB_22 0.007358 _diffrn_orient_matrix_UB_23 0.054199 _diffrn_orient_matrix_UB_31 -0.102902 _diffrn_orient_matrix_UB_32 -0.019229 _diffrn_orient_matrix_UB_33 0.008663 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_xray_symbol K-L~3~ _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0651 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 21478 _diffrn_reflns_theta_full 26.38 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 1.14 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7127 _reflns_number_total 10178 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection 'SMART v5.630 (Bruker, 2003)' _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.640 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.067 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 775 _refine_ls_number_reflns 10178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0507 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+1.6620P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1052 _refine_ls_wR_factor_ref 0.1162 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.05970(8) 0.21907(5) 0.34120(4) 0.01748(16) Uani 1 1 d . . . F7B3 F -0.04651(19) 0.37323(13) 0.31379(9) 0.0293(4) Uani 1 1 d . . . F7B1 F -0.10671(18) 0.27589(12) 0.20570(10) 0.0300(4) Uani 1 1 d . . . F7A3 F 0.05878(19) 0.08900(12) 0.20726(9) 0.0290(4) Uani 1 1 d . . . F7B2 F -0.02115(18) 0.43013(12) 0.21425(9) 0.0286(4) Uani 1 1 d . . . C1B C 0.1869(3) 0.2947(2) 0.28807(15) 0.0188(6) Uani 1 1 d . . . F7C3 F -0.1026(2) 0.11626(13) 0.44961(11) 0.0407(5) Uani 1 1 d . . . C1A C 0.1587(3) 0.14070(19) 0.36620(15) 0.0181(6) Uani 1 1 d . . . F7A1 F -0.09121(19) -0.01936(13) 0.25358(11) 0.0386(5) Uani 1 1 d . . . F7C1 F -0.2376(2) 0.19165(14) 0.41353(11) 0.0385(5) Uani 1 1 d . . . F7C2 F -0.2079(2) 0.18542(15) 0.52872(11) 0.0469(5) Uani 1 1 d . . . F7A2 F 0.0773(2) -0.05164(13) 0.19857(11) 0.0448(5) Uani 1 1 d . . . C1C C 0.0882(3) 0.3063(2) 0.43128(15) 0.0197(6) Uani 1 1 d . . . C2C C 0.2009(3) 0.3947(2) 0.44838(15) 0.0222(6) Uani 1 1 d . . . H2C H 0.2703 0.4090 0.4149 0.027 Uiso 1 1 calc R . . C6A C 0.1438(3) 0.0517(2) 0.31833(16) 0.0208(6) Uani 1 1 d . . . C6B C 0.1426(3) 0.35329(19) 0.24645(15) 0.0193(6) Uani 1 1 d . . . C2B C 0.3246(3) 0.2906(2) 0.28306(15) 0.0195(6) Uani 1 1 d . . . H2B H 0.3572 0.2515 0.3104 0.023 Uiso 1 1 calc R . . C7B C -0.0070(3) 0.3582(2) 0.24522(15) 0.0218(6) Uani 1 1 d . . . C6C C -0.0121(3) 0.2877(2) 0.48264(16) 0.0223(6) Uani 1 1 d . . . C5B C 0.2345(3) 0.4056(2) 0.20303(16) 0.0247(7) Uani 1 1 d . . . H5B H 0.2032 0.4450 0.1755 0.030 Uiso 1 1 calc R . . C5A C 0.2110(3) -0.0098(2) 0.33923(17) 0.0248(7) Uani 1 1 d . . . H5A H 0.2021 -0.0683 0.3054 0.030 Uiso 1 1 calc R . . C2A C 0.2406(3) 0.1620(2) 0.43521(15) 0.0211(6) Uani 1 1 d . . . H2A H 0.2533 0.2216 0.4687 0.025 Uiso 1 1 calc R . . C3A C 0.3046(3) 0.0992(2) 0.45696(16) 0.0228(6) Uani 1 1 d . . . C3C C 0.2140(3) 0.4627(2) 0.51367(16) 0.0255(7) Uani 1 1 d . . . C3B C 0.4151(3) 0.3423(2) 0.23916(16) 0.0216(6) Uani 1 1 d . . . C4B C 0.3708(3) 0.4010(2) 0.19950(16) 0.0260(7) Uani 1 1 d . . . H4B H 0.4337 0.4376 0.1702 0.031 Uiso 1 1 calc R . . C4A C 0.2907(3) 0.0128(2) 0.40840(17) 0.0268(7) Uani 1 1 d . . . H4A H 0.3354 -0.0301 0.4227 0.032 Uiso 1 1 calc R . . C5C C 0.0040(4) 0.3561(2) 0.54791(17) 0.0307(8) Uani 1 1 d . . . H5C H -0.0636 0.3423 0.5824 0.037 Uiso 1 1 calc R . . C7C C -0.1404(4) 0.1953(2) 0.46841(18) 0.0310(8) Uani 1 1 d . . . C8B C 0.5637(3) 0.3376(2) 0.23354(18) 0.0304(7) Uani 1 1 d . . . C7A C 0.0481(3) 0.0175(2) 0.24427(17) 0.0264(7) Uani 1 1 d . . . C4C C 0.1155(4) 0.4431(2) 0.56355(16) 0.0292(7) Uani 1 1 d . . . H4C H 0.1247 0.4894 0.6082 0.035 Uiso 1 1 calc R . . C8C C 0.3386(4) 0.5570(2) 0.53162(18) 0.0361(8) Uani 1 1 d . . . C8A C 0.3852(4) 0.1259(2) 0.53364(18) 0.0330(8) Uani 1 1 d . . . P2 P 0.38603(8) 0.78548(5) 0.15865(4) 0.01599(16) Uani 1 1 d . . . F7F2 F 0.23756(19) 0.74777(12) 0.30679(10) 0.0308(4) Uani 1 1 d . . . F7F1 F 0.16450(17) 0.63198(12) 0.20883(9) 0.0262(4) Uani 1 1 d . . . F7E2 F 0.4292(2) 1.01333(13) 0.21852(10) 0.0355(5) Uani 1 1 d . . . F7D1 F 0.08038(19) 0.79294(12) 0.09253(10) 0.0305(4) Uani 1 1 d . . . F7F3 F 0.19326(18) 0.59956(12) 0.31701(9) 0.0286(4) Uani 1 1 d . . . F7D3 F 0.26947(18) 0.87135(12) 0.04887(10) 0.0304(4) Uani 1 1 d . . . F7E3 F 0.5448(2) 0.94600(12) 0.28122(9) 0.0337(4) Uani 1 1 d . . . C2D C 0.3313(3) 0.60217(19) 0.05973(15) 0.0178(6) Uani 1 1 d . . . H2D H 0.4000 0.5927 0.0932 0.021 Uiso 1 1 calc R . . F7D2 F 0.07271(19) 0.79149(12) -0.02469(10) 0.0321(4) Uani 1 1 d . . . F7E1 F 0.6485(2) 1.09074(12) 0.26599(10) 0.0415(5) Uani 1 1 d . . . C1E C 0.5394(3) 0.86574(19) 0.12283(15) 0.0163(6) Uani 1 1 d . . . C2F C 0.6222(3) 0.73467(19) 0.21290(14) 0.0169(6) Uani 1 1 d . . . H2F H 0.6752 0.7705 0.1799 0.020 Uiso 1 1 calc R . . C1D C 0.3024(3) 0.68894(19) 0.07395(15) 0.0153(6) Uani 1 1 d . . . C3D C 0.2609(3) 0.5292(2) -0.00272(16) 0.0201(6) Uani 1 1 d . . . C1F C 0.4778(3) 0.72490(19) 0.21435(14) 0.0167(6) Uani 1 1 d . . . C4F C 0.6158(3) 0.6407(2) 0.30692(16) 0.0227(6) Uani 1 1 d . . . H4F H 0.6627 0.6119 0.3377 0.027 Uiso 1 1 calc R . . C6D C 0.1990(3) 0.6997(2) 0.02301(15) 0.0185(6) Uani 1 1 d . . . C6F C 0.4041(3) 0.67268(19) 0.26546(15) 0.0195(6) Uani 1 1 d . . . C3F C 0.6905(3) 0.6934(2) 0.25849(15) 0.0188(6) Uani 1 1 d . . . C3E C 0.6980(3) 0.8987(2) 0.02849(15) 0.0190(6) Uani 1 1 d . . . C2E C 0.5874(3) 0.8358(2) 0.05625(15) 0.0190(6) Uani 1 1 d . . . H2E H 0.5433 0.7707 0.0292 0.023 Uiso 1 1 calc R . . C5F C 0.4728(3) 0.6303(2) 0.31025(16) 0.0225(6) Uani 1 1 d . . . H5F H 0.4211 0.5939 0.3433 0.027 Uiso 1 1 calc R . . C6E C 0.6064(3) 0.96357(19) 0.16074(15) 0.0195(6) Uani 1 1 d . . . C7F C 0.2507(3) 0.6633(2) 0.27441(16) 0.0227(7) Uani 1 1 d . . . C7E C 0.5579(3) 1.0036(2) 0.23170(17) 0.0258(7) Uani 1 1 d . . . C4E C 0.7643(3) 0.9940(2) 0.06704(17) 0.0242(7) Uani 1 1 d . . . H4E H 0.8411 1.0369 0.0483 0.029 Uiso 1 1 calc R . . C8E C 0.7424(3) 0.8659(2) -0.04511(17) 0.0270(7) Uani 1 1 d . . . C8D C 0.2894(3) 0.4353(2) -0.01727(18) 0.0270(7) Uani 1 1 d . . . C5E C 0.7177(3) 1.0259(2) 0.13299(17) 0.0241(7) Uani 1 1 d . . . H5E H 0.7624 1.0912 0.1595 0.029 Uiso 1 1 calc R . . C4D C 0.1610(3) 0.5415(2) -0.05244(16) 0.0239(7) Uani 1 1 d . . . H4D H 0.1137 0.4918 -0.0952 0.029 Uiso 1 1 calc R . . C5D C 0.1304(3) 0.6267(2) -0.03934(16) 0.0230(6) Uani 1 1 d . . . H5D H 0.0617 0.6354 -0.0733 0.028 Uiso 1 1 calc R . . C8F C 0.8480(3) 0.7073(2) 0.25828(17) 0.0260(7) Uani 1 1 d . . . C7D C 0.1553(3) 0.7883(2) 0.03535(17) 0.0235(7) Uani 1 1 d . . . F8D1 F 0.39307(18) 0.43255(11) 0.03151(9) 0.0275(4) Uani 1 1 d . . . F8F1 F 0.90154(19) 0.74226(15) 0.20107(11) 0.0410(5) Uani 1 1 d . . . F8B3 F 0.66599(19) 0.42109(14) 0.26676(12) 0.0430(5) Uani 1 1 d . . . F8D3 F 0.3294(2) 0.41687(14) -0.08528(10) 0.0416(5) Uani 1 1 d . . . F8A1 F 0.3050(2) 0.14439(16) 0.58619(10) 0.0453(5) Uani 1 1 d . . . F8C3 F 0.4056(3) 0.57704(15) 0.47337(11) 0.0778(9) Uani 1 1 d . . . F8E1 F 0.7270(2) 0.77174(13) -0.05883(11) 0.0447(5) Uani 1 1 d . . . F8F2 F 0.9271(2) 0.76806(17) 0.31973(11) 0.0526(6) Uani 1 1 d . . . F8D2 F 0.1717(2) 0.36046(13) -0.01560(15) 0.0564(7) Uani 1 1 d . . . F8E2 F 0.6639(2) 0.87769(16) -0.10184(10) 0.0480(5) Uani 1 1 d . . . F8B2 F 0.5889(2) 0.32056(18) 0.16291(11) 0.0571(6) Uani 1 1 d . . . F8F3 F 0.8727(2) 0.62395(15) 0.25597(14) 0.0525(6) Uani 1 1 d . . . F8B1 F 0.5873(2) 0.26989(15) 0.26475(14) 0.0521(6) Uani 1 1 d . . . F8C2 F 0.4394(2) 0.55608(17) 0.58185(13) 0.0599(6) Uani 1 1 d . . . F8E3 F 0.8797(2) 0.91360(15) -0.04999(11) 0.0499(6) Uani 1 1 d . . . F8A2 F 0.4310(3) 0.05658(17) 0.55044(11) 0.0571(7) Uani 1 1 d . . . F8A3 F 0.5010(2) 0.20649(17) 0.54329(12) 0.0567(6) Uani 1 1 d . . . F8C1 F 0.2988(3) 0.63026(15) 0.56119(16) 0.0782(8) 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 P1 0.0187(4) 0.0176(4) 0.0159(4) 0.0018(3) 0.0030(3) 0.0067(3) F7B3 0.0330(10) 0.0407(11) 0.0214(9) 0.0063(8) 0.0055(8) 0.0221(9) F7B1 0.0233(9) 0.0237(9) 0.0360(10) 0.0004(8) -0.0040(8) 0.0033(8) F7A3 0.0380(11) 0.0263(9) 0.0208(9) 0.0035(7) 0.0024(8) 0.0097(8) F7B2 0.0324(10) 0.0256(9) 0.0296(10) 0.0100(8) -0.0016(8) 0.0109(8) C1B 0.0206(15) 0.0188(15) 0.0136(14) 0.0006(11) 0.0020(12) 0.0036(12) F7C3 0.0403(12) 0.0269(10) 0.0595(13) 0.0150(9) 0.0247(10) 0.0111(9) C1A 0.0172(15) 0.0169(14) 0.0215(15) 0.0055(12) 0.0081(12) 0.0058(12) F7A1 0.0244(10) 0.0382(11) 0.0450(12) 0.0127(9) -0.0044(9) -0.0006(9) F7C1 0.0297(11) 0.0421(11) 0.0376(11) 0.0013(9) 0.0001(9) 0.0086(9) F7C2 0.0447(12) 0.0566(13) 0.0343(11) 0.0094(10) 0.0251(10) 0.0067(10) F7A2 0.0601(14) 0.0338(11) 0.0367(11) -0.0157(9) -0.0107(10) 0.0266(10) C1C 0.0259(16) 0.0228(15) 0.0134(14) 0.0019(12) 0.0011(12) 0.0139(13) C2C 0.0320(17) 0.0227(16) 0.0149(14) 0.0044(12) 0.0030(13) 0.0131(14) C6A 0.0195(15) 0.0198(15) 0.0225(15) 0.0038(12) 0.0048(12) 0.0059(12) C6B 0.0223(15) 0.0160(14) 0.0146(14) -0.0014(11) 0.0009(12) 0.0026(12) C2B 0.0220(15) 0.0184(15) 0.0161(14) 0.0006(11) 0.0001(12) 0.0064(12) C7B 0.0288(17) 0.0197(15) 0.0167(15) 0.0042(12) 0.0012(13) 0.0083(13) C6C 0.0253(16) 0.0268(16) 0.0191(15) 0.0056(12) 0.0031(13) 0.0143(13) C5B 0.0334(18) 0.0201(15) 0.0199(15) 0.0044(12) 0.0022(13) 0.0084(14) C5A 0.0262(17) 0.0192(15) 0.0289(17) 0.0022(13) 0.0050(14) 0.0090(13) C2A 0.0230(16) 0.0224(15) 0.0175(15) 0.0016(12) 0.0060(12) 0.0080(13) C3A 0.0216(16) 0.0276(16) 0.0224(16) 0.0069(13) 0.0033(13) 0.0119(13) C3C 0.0354(18) 0.0197(15) 0.0216(16) 0.0017(12) -0.0017(14) 0.0120(14) C3B 0.0225(16) 0.0178(15) 0.0193(15) -0.0018(12) 0.0038(12) 0.0030(13) C4B 0.0272(17) 0.0245(16) 0.0204(16) 0.0061(13) 0.0049(13) -0.0002(14) C4A 0.0268(17) 0.0279(17) 0.0319(18) 0.0089(14) 0.0054(14) 0.0160(14) C5C 0.0343(19) 0.044(2) 0.0188(16) 0.0056(14) 0.0093(14) 0.0193(16) C7C 0.0297(18) 0.0368(19) 0.0292(18) 0.0084(15) 0.0148(15) 0.0123(15) C8B 0.0255(18) 0.0297(18) 0.0311(18) 0.0033(14) 0.0106(15) 0.0033(15) C7A 0.0271(18) 0.0194(16) 0.0296(17) -0.0012(13) 0.0011(14) 0.0078(14) C4C 0.041(2) 0.0327(18) 0.0169(15) -0.0033(13) 0.0026(14) 0.0215(16) C8C 0.055(2) 0.0225(17) 0.0239(18) -0.0039(14) -0.0002(17) 0.0103(16) C8A 0.036(2) 0.040(2) 0.0291(18) 0.0072(15) 0.0020(15) 0.0214(17) P2 0.0161(4) 0.0150(4) 0.0155(4) 0.0021(3) 0.0026(3) 0.0038(3) F7F2 0.0324(10) 0.0293(10) 0.0344(10) 0.0049(8) 0.0148(8) 0.0146(8) F7F1 0.0182(9) 0.0342(10) 0.0250(9) 0.0087(8) 0.0054(7) 0.0056(8) F7E2 0.0385(11) 0.0364(11) 0.0354(11) 0.0026(8) 0.0091(9) 0.0199(9) F7D1 0.0321(10) 0.0281(10) 0.0339(10) 0.0021(8) 0.0074(8) 0.0155(8) F7F3 0.0272(10) 0.0316(10) 0.0296(10) 0.0128(8) 0.0151(8) 0.0081(8) F7D3 0.0232(9) 0.0188(9) 0.0444(11) 0.0099(8) -0.0062(8) 0.0009(8) F7E3 0.0507(12) 0.0276(10) 0.0199(9) 0.0021(8) 0.0016(8) 0.0117(9) C2D 0.0162(14) 0.0179(14) 0.0181(14) 0.0039(11) 0.0033(12) 0.0039(12) F7D2 0.0307(10) 0.0286(10) 0.0358(10) 0.0098(8) -0.0096(8) 0.0096(8) F7E1 0.0493(13) 0.0217(10) 0.0362(11) -0.0113(8) 0.0013(10) -0.0008(9) C1E 0.0157(14) 0.0139(14) 0.0172(14) 0.0039(11) -0.0015(11) 0.0027(11) C2F 0.0223(15) 0.0145(14) 0.0126(13) 0.0015(11) 0.0032(12) 0.0050(12) C1D 0.0119(14) 0.0149(14) 0.0163(14) 0.0042(11) 0.0048(11) -0.0003(11) C3D 0.0161(15) 0.0195(15) 0.0212(15) 0.0006(12) 0.0063(12) 0.0028(12) C1F 0.0214(15) 0.0138(14) 0.0111(13) -0.0019(11) 0.0011(11) 0.0038(12) C4F 0.0276(17) 0.0231(16) 0.0185(15) 0.0053(12) 0.0008(13) 0.0101(13) C6D 0.0167(14) 0.0187(14) 0.0188(14) 0.0075(12) 0.0059(12) 0.0019(12) C6F 0.0238(16) 0.0149(14) 0.0163(14) -0.0013(11) 0.0042(12) 0.0040(12) C3F 0.0193(15) 0.0170(14) 0.0167(14) -0.0016(11) -0.0003(12) 0.0049(12) C3E 0.0151(14) 0.0228(15) 0.0201(15) 0.0061(12) -0.0002(12) 0.0075(12) C2E 0.0163(15) 0.0148(14) 0.0216(15) 0.0032(12) -0.0009(12) 0.0004(12) C5F 0.0288(17) 0.0205(15) 0.0158(14) 0.0049(12) 0.0035(13) 0.0048(13) C6E 0.0201(15) 0.0146(14) 0.0204(15) 0.0017(11) -0.0054(12) 0.0040(12) C7F 0.0262(17) 0.0249(16) 0.0183(15) 0.0072(12) 0.0079(13) 0.0080(13) C7E 0.0287(18) 0.0175(15) 0.0241(16) -0.0017(13) -0.0023(14) 0.0026(13) C4E 0.0177(15) 0.0228(16) 0.0334(18) 0.0142(13) 0.0031(13) 0.0041(13) C8E 0.0232(17) 0.0291(17) 0.0261(17) 0.0097(14) 0.0066(14) 0.0028(14) C8D 0.0170(16) 0.0222(16) 0.0359(19) -0.0023(14) 0.0033(14) 0.0032(13) C5E 0.0248(16) 0.0137(14) 0.0286(17) 0.0016(12) -0.0036(13) 0.0027(13) C4D 0.0197(15) 0.0238(16) 0.0198(15) -0.0047(12) 0.0007(12) 0.0016(13) C5D 0.0216(16) 0.0275(16) 0.0176(15) 0.0042(12) -0.0012(12) 0.0065(13) C8F 0.0240(17) 0.0279(17) 0.0275(17) 0.0084(14) 0.0040(14) 0.0093(14) C7D 0.0187(15) 0.0211(16) 0.0273(16) 0.0072(13) -0.0022(13) 0.0022(13) F8D1 0.0315(10) 0.0214(9) 0.0296(10) 0.0038(7) 0.0036(8) 0.0099(8) F8F1 0.0239(10) 0.0652(14) 0.0433(12) 0.0288(11) 0.0126(9) 0.0170(10) F8B3 0.0219(10) 0.0375(11) 0.0592(14) -0.0011(10) -0.0017(9) 0.0034(9) F8D3 0.0427(12) 0.0511(12) 0.0296(10) -0.0157(9) -0.0042(9) 0.0291(10) F8A1 0.0549(13) 0.0679(14) 0.0232(10) 0.0035(10) 0.0051(9) 0.0378(12) F8C3 0.129(2) 0.0340(12) 0.0256(11) 0.0012(9) 0.0149(13) -0.0295(13) F8E1 0.0662(15) 0.0322(11) 0.0403(12) 0.0082(9) 0.0304(11) 0.0183(10) F8F2 0.0241(11) 0.0785(16) 0.0395(12) -0.0078(11) -0.0079(9) 0.0096(11) F8D2 0.0240(11) 0.0174(10) 0.119(2) 0.0030(11) 0.0121(12) 0.0010(8) F8E2 0.0561(14) 0.0738(15) 0.0221(10) 0.0153(10) 0.0051(10) 0.0303(12) F8B2 0.0332(12) 0.0971(18) 0.0337(12) -0.0035(12) 0.0138(10) 0.0199(12) F8F3 0.0328(11) 0.0442(12) 0.0991(18) 0.0346(12) 0.0246(12) 0.0249(10) F8B1 0.0353(12) 0.0475(13) 0.0932(18) 0.0352(12) 0.0321(12) 0.0253(10) F8C2 0.0414(13) 0.0639(15) 0.0537(14) 0.0113(12) -0.0118(11) -0.0057(11) F8E3 0.0281(11) 0.0622(14) 0.0404(12) -0.0007(10) 0.0167(9) -0.0061(10) F8A2 0.0866(18) 0.0726(16) 0.0331(11) 0.0035(11) -0.0082(11) 0.0622(14) F8A3 0.0393(13) 0.0771(16) 0.0380(12) 0.0070(11) -0.0124(10) 0.0049(12) F8C1 0.0770(18) 0.0266(12) 0.115(2) -0.0182(13) -0.0018(16) 0.0166(12) _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 C1B 1.855(3) . ? P1 C1A 1.847(3) . ? P1 C1C 1.854(3) . ? F7B3 C7B 1.344(3) . ? F7B1 C7B 1.345(3) . ? F7A3 C7A 1.344(3) . ? F7B2 C7B 1.340(3) . ? C1B C6B 1.409(4) . ? C1B C2B 1.392(4) . ? F7C3 C7C 1.341(4) . ? C1A C6A 1.411(4) . ? C1A C2A 1.387(4) . ? F7A1 C7A 1.344(3) . ? F7C1 C7C 1.330(4) . ? F7C2 C7C 1.336(3) . ? F7A2 C7A 1.327(3) . ? C1C C2C 1.390(4) . ? C1C C6C 1.410(4) . ? C2C C3C 1.392(4) . ? C6A C5A 1.385(4) . ? C6A C7A 1.511(4) . ? C6B C7B 1.507(4) . ? C6B C5B 1.389(4) . ? C2B C3B 1.383(4) . ? C6C C5C 1.389(4) . ? C6C C7C 1.508(4) . ? C5B C4B 1.378(4) . ? C5A C4A 1.377(4) . ? C2A C3A 1.388(4) . ? C3A C4A 1.387(4) . ? C3A C8A 1.493(4) . ? C3C C4C 1.379(4) . ? C3C C8C 1.504(4) . ? C3B C4B 1.387(4) . ? C3B C8B 1.505(4) . ? C5C C4C 1.371(5) . ? C8B F8B3 1.333(4) . ? C8B F8B2 1.332(4) . ? C8B F8B1 1.321(4) . ? C8C F8C3 1.324(4) . ? C8C F8C2 1.320(4) . ? C8C F8C1 1.317(4) . ? C8A F8A1 1.335(4) . ? C8A F8A2 1.330(4) . ? C8A F8A3 1.339(4) . ? P2 C1E 1.845(3) . ? P2 C1D 1.853(3) . ? P2 C1F 1.853(3) . ? F7F2 C7F 1.341(3) . ? F7F1 C7F 1.344(3) . ? F7E2 C7E 1.340(4) . ? F7D1 C7D 1.329(3) . ? F7F3 C7F 1.346(3) . ? F7D3 C7D 1.348(3) . ? F7E3 C7E 1.344(3) . ? C2D C1D 1.395(4) . ? C2D C3D 1.393(4) . ? F7D2 C7D 1.348(3) . ? F7E1 C7E 1.329(3) . ? C1E C2E 1.391(4) . ? C1E C6E 1.413(4) . ? C2F C1F 1.392(4) . ? C2F C3F 1.386(4) . ? C1D C6D 1.410(4) . ? C3D C8D 1.496(4) . ? C3D C4D 1.382(4) . ? C1F C6F 1.415(4) . ? C4F C3F 1.383(4) . ? C4F C5F 1.380(4) . ? C6D C5D 1.389(4) . ? C6D C7D 1.501(4) . ? C6F C5F 1.390(4) . ? C6F C7F 1.503(4) . ? C3F C8F 1.505(4) . ? C3E C2E 1.384(4) . ? C3E C4E 1.386(4) . ? C3E C8E 1.496(4) . ? C6E C7E 1.507(4) . ? C6E C5E 1.384(4) . ? C4E C5E 1.383(4) . ? C8E F8E1 1.335(4) . ? C8E F8E2 1.332(4) . ? C8E F8E3 1.332(3) . ? C8D F8D1 1.335(3) . ? C8D F8D3 1.343(3) . ? C8D F8D2 1.333(3) . ? C4D C5D 1.381(4) . ? C8F F8F1 1.322(3) . ? C8F F8F2 1.330(4) . ? C8F F8F3 1.335(3) . ? 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 F7B3 C7B F7B1 106.6(2) . . ? F7B3 C7B C6B 112.8(2) . . ? F7B1 C7B C6B 112.0(2) . . ? F7A3 C7A F7A1 106.5(2) . . ? F7A3 C7A C6A 113.0(2) . . ? F7B2 C7B F7B3 106.1(2) . . ? F7B2 C7B F7B1 106.2(2) . . ? F7B2 C7B C6B 112.6(2) . . ? C1B C6B C7B 121.3(2) . . ? F7C3 C7C C6C 111.9(3) . . ? C1A P1 C1B 101.51(12) . . ? C1A P1 C1C 101.08(12) . . ? C1A C6A C7A 121.4(3) . . ? C1A C2A C3A 122.1(3) . . ? F7A1 C7A C6A 111.1(2) . . ? F7C1 C7C F7C3 107.0(3) . . ? F7C1 C7C F7C2 106.8(3) . . ? F7C1 C7C C6C 112.2(3) . . ? F7C2 C7C F7C3 106.6(3) . . ? F7C2 C7C C6C 111.8(3) . . ? F7A2 C7A F7A3 106.5(2) . . ? F7A2 C7A F7A1 106.8(2) . . ? F7A2 C7A C6A 112.6(2) . . ? C1C P1 C1B 100.91(13) . . ? C1C C2C C3C 121.2(3) . . ? C1C C6C C7C 121.8(3) . . ? C2C C1C P1 122.0(2) . . ? C2C C1C C6C 117.6(3) . . ? C2C C3C C8C 120.2(3) . . ? C6A C1A P1 121.2(2) . . ? C6B C1B P1 120.4(2) . . ? C2B C1B P1 121.9(2) . . ? C2B C1B C6B 117.5(3) . . ? C2B C3B C4B 120.4(3) . . ? C2B C3B C8B 121.5(3) . . ? C6C C1C P1 120.2(2) . . ? C5B C6B C1B 120.7(3) . . ? C5B C6B C7B 117.9(3) . . ? C5B C4B C3B 119.3(3) . . ? C5A C6A C1A 121.0(3) . . ? C5A C6A C7A 117.5(3) . . ? C5A C4A C3A 119.0(3) . . ? C2A C1A P1 121.8(2) . . ? C2A C1A C6A 116.8(3) . . ? C2A C3A C8A 118.5(3) . . ? C3B C2B C1B 121.5(3) . . ? C4B C5B C6B 120.7(3) . . ? C4B C3B C8B 118.1(3) . . ? C4A C5A C6A 120.9(3) . . ? C4A C3A C2A 120.1(3) . . ? C4A C3A C8A 121.5(3) . . ? C5C C6C C1C 120.2(3) . . ? C5C C6C C7C 118.0(3) . . ? C5C C4C C3C 119.2(3) . . ? C4C C3C C2C 120.4(3) . . ? C4C C3C C8C 119.3(3) . . ? C4C C5C C6C 121.3(3) . . ? F7F2 C7F F7F1 106.8(2) . . ? F7F2 C7F F7F3 106.5(2) . . ? F7F2 C7F C6F 112.4(2) . . ? F7F1 C7F F7F3 106.2(2) . . ? F7F1 C7F C6F 112.5(2) . . ? F7E2 C7E F7E3 106.7(2) . . ? F7E2 C7E C6E 111.6(2) . . ? F7D1 C7D F7D3 106.9(2) . . ? F7D1 C7D F7D2 106.6(2) . . ? F7D1 C7D C6D 112.5(2) . . ? F7F3 C7F C6F 112.1(2) . . ? F7D3 C7D F7D2 105.8(2) . . ? F7D3 C7D C6D 112.4(2) . . ? F7E3 C7E C6E 112.4(2) . . ? C2D C1D P2 122.8(2) . . ? C2D C1D C6D 117.5(2) . . ? C2D C3D C8D 121.2(3) . . ? F7D2 C7D C6D 112.2(2) . . ? F7E1 C7E F7E2 106.6(2) . . ? F7E1 C7E F7E3 106.8(2) . . ? F7E1 C7E C6E 112.4(3) . . ? C1E P2 C1D 100.86(12) . . ? C1E P2 C1F 101.29(12) . . ? C1E C6E C7E 121.3(3) . . ? C2F C1F P2 122.7(2) . . ? C2F C1F C6F 117.2(3) . . ? C2F C3F C8F 121.0(3) . . ? C1D C6D C7D 121.5(2) . . ? C3D C2D C1D 121.1(3) . . ? C1F P2 C1D 101.93(12) . . ? C1F C6F C7F 121.2(3) . . ? C4F C3F C2F 120.4(3) . . ? C4F C3F C8F 118.6(3) . . ? C4F C5F C6F 120.3(3) . . ? C6D C1D P2 119.6(2) . . ? C6F C1F P2 119.9(2) . . ? C3F C2F C1F 121.5(3) . . ? C3E C2E C1E 121.5(3) . . ? C2E C1E P2 122.5(2) . . ? C2E C1E C6E 117.4(2) . . ? C2E C3E C4E 120.3(3) . . ? C2E C3E C8E 120.3(3) . . ? C5F C4F C3F 119.6(3) . . ? C5F C6F C1F 120.9(3) . . ? C5F C6F C7F 117.9(2) . . ? C6E C1E P2 119.9(2) . . ? C4E C3E C8E 119.4(3) . . ? C4E C5E C6E 120.6(3) . . ? C5E C6E C1E 120.7(3) . . ? C5E C6E C7E 118.0(2) . . ? C5E C4E C3E 119.4(3) . . ? C4D C3D C2D 120.6(3) . . ? C4D C3D C8D 118.2(3) . . ? C4D C5D C6D 120.8(3) . . ? C5D C6D C1D 120.7(3) . . ? C5D C6D C7D 117.7(3) . . ? C5D C4D C3D 119.3(3) . . ? F8D1 C8D C3D 113.7(2) . . ? F8D1 C8D F8D3 106.5(2) . . ? F8F1 C8F C3F 113.2(2) . . ? F8F1 C8F F8F2 106.8(3) . . ? F8F1 C8F F8F3 106.9(2) . . ? F8B3 C8B C3B 112.0(3) . . ? F8D3 C8D C3D 111.5(3) . . ? F8A1 C8A C3A 112.1(3) . . ? F8A1 C8A F8A3 105.6(3) . . ? F8C3 C8C C3C 113.3(3) . . ? F8E1 C8E C3E 112.6(2) . . ? F8F2 C8F C3F 111.8(2) . . ? F8F2 C8F F8F3 106.1(3) . . ? F8D2 C8D C3D 111.5(2) . . ? F8D2 C8D F8D1 107.1(3) . . ? F8D2 C8D F8D3 106.1(2) . . ? F8E2 C8E C3E 112.0(3) . . ? F8E2 C8E F8E1 105.9(3) . . ? F8E2 C8E F8E3 106.9(2) . . ? F8B2 C8B C3B 111.9(3) . . ? F8B2 C8B F8B3 105.7(3) . . ? F8F3 C8F C3F 111.6(2) . . ? F8B1 C8B C3B 113.0(3) . . ? F8B1 C8B F8B3 106.3(3) . . ? F8B1 C8B F8B2 107.5(3) . . ? F8C2 C8C C3C 111.9(3) . . ? F8C2 C8C F8C3 104.8(3) . . ? F8E3 C8E C3E 112.7(3) . . ? F8E3 C8E F8E1 106.3(3) . . ? F8A2 C8A C3A 113.0(3) . . ? F8A2 C8A F8A1 106.4(3) . . ? F8A2 C8A F8A3 107.0(3) . . ? F8A3 C8A C3A 112.2(3) . . ? F8C1 C8C C3C 111.7(3) . . ? F8C1 C8C F8C3 109.5(3) . . ? F8C1 C8C F8C2 105.1(3) . . ?