Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Alder, R.' 'Butts, Craig P.' 'Orpen, A.' 'Read, David' _publ_contact_author_name 'Prof R Alder' _publ_contact_author_address ; Prof R Alder School of Chemistry University of Bristol Bristol BS8 1TS UNITED KINGDOM ; data_fftoh _database_code_CSD 152497 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H22 F6 O P3' _chemical_formula_weight 377.20 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' 'P' 'P' 0.1023 0.0942 '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' 'O' 'O' 0.0106 0.0060 '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 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 12.997(3) _cell_length_b 15.552(2) _cell_length_c 15.809(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3195.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 4.98 _cell_measurement_theta_max 12.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .6 _exptl_crystal_size_mid .43 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 8.04 _diffrn_reflns_number 2822 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1456 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2822 _reflns_number_gt 1238 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0680P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2822 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_restrained_S_all 0.783 _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 0.12127(10) 0.11992(9) 0.41487(9) 0.0229(3) Uani 1 1 d . . . P2 P 0.30590(10) 0.16782(9) 0.41984(10) 0.0262(4) Uani 1 1 d . . . O1 O -0.0051(2) 0.1010(2) 0.4192(2) 0.0329(9) Uani 1 1 d . . . C1 C 0.1259(4) 0.1384(3) 0.3004(3) 0.0298(14) Uani 1 1 d . . . H1A H 0.0683 0.1075 0.2761 0.036 Uiso 1 1 calc R . . H1B H 0.1125 0.1991 0.2917 0.036 Uiso 1 1 calc R . . C2 C 0.2198(4) 0.1161(4) 0.2473(4) 0.0379(15) Uani 1 1 d . . . H2A H 0.1975 0.1079 0.1894 0.045 Uiso 1 1 calc R . . H2B H 0.2469 0.0616 0.2672 0.045 Uiso 1 1 calc R . . C3 C 0.3074(5) 0.1815(4) 0.2473(4) 0.0433(15) Uani 1 1 d . . . H3A H 0.3464 0.1756 0.1953 0.052 Uiso 1 1 calc R . . H3B H 0.2785 0.2390 0.2485 0.052 Uiso 1 1 calc R . . C4 C 0.3792(4) 0.1710(4) 0.3215(4) 0.0360(15) Uani 1 1 d . . . H4A H 0.4274 0.2186 0.3231 0.043 Uiso 1 1 calc R . . H4B H 0.4182 0.1182 0.3153 0.043 Uiso 1 1 calc R . . C5 C 0.1665(4) 0.0160(3) 0.4514(3) 0.0257(13) Uani 1 1 d . . . H5A H 0.1063 -0.0186 0.4641 0.031 Uiso 1 1 calc R . . H5B H 0.2013 -0.0114 0.4044 0.031 Uiso 1 1 calc R . . C6 C 0.2384(4) 0.0107(4) 0.5281(4) 0.0322(14) Uani 1 1 d . . . H6A H 0.2178 0.0546 0.5682 0.039 Uiso 1 1 calc R . . H6B H 0.2279 -0.0446 0.5552 0.039 Uiso 1 1 calc R . . C7 C 0.3523(4) 0.0211(3) 0.5110(4) 0.0371(16) Uani 1 1 d . . . H7A H 0.3699 -0.0100 0.4598 0.045 Uiso 1 1 calc R . . H7B H 0.3908 -0.0041 0.5573 0.045 Uiso 1 1 calc R . . C8 C 0.3841(4) 0.1150(3) 0.5008(4) 0.0379(15) Uani 1 1 d . . . H8A H 0.4561 0.1179 0.4849 0.045 Uiso 1 1 calc R . . H8B H 0.3758 0.1447 0.5543 0.045 Uiso 1 1 calc R . . C9 C 0.1022(4) 0.2128(3) 0.4832(4) 0.0293(14) Uani 1 1 d . . . H9A H 0.0623 0.2543 0.4512 0.035 Uiso 1 1 calc R . . H9B H 0.0592 0.1941 0.5298 0.035 Uiso 1 1 calc R . . C10 C 0.1935(4) 0.2614(3) 0.5217(3) 0.0364(15) Uani 1 1 d . . . H10A H 0.1701 0.3168 0.5423 0.044 Uiso 1 1 calc R . . H10B H 0.2199 0.2293 0.5696 0.044 Uiso 1 1 calc R . . C11 C 0.2797(4) 0.2751(3) 0.4578(4) 0.0345(15) Uani 1 1 d . . . H11A H 0.3400 0.2999 0.4846 0.041 Uiso 1 1 calc R . . H11B H 0.2577 0.3124 0.4121 0.041 Uiso 1 1 calc R . . P3 P 0.54045(14) 0.09842(10) 0.74851(11) 0.0402(4) Uani 1 1 d . . . F1 F 0.4845(4) 0.0290(3) 0.6894(3) 0.112(2) Uani 1 1 d . . . F2 F 0.6373(3) 0.0967(3) 0.6910(3) 0.0987(17) Uani 1 1 d . . . F3 F 0.5913(3) 0.1680(3) 0.8066(3) 0.0790(15) Uani 1 1 d . . . F4 F 0.4368(4) 0.1011(3) 0.8034(3) 0.1113(19) Uani 1 1 d . . . F5 F 0.5836(3) 0.0223(2) 0.8052(2) 0.0596(12) Uani 1 1 d . . . F6 F 0.4877(3) 0.1738(2) 0.6903(2) 0.0698(13) 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 0.0195(7) 0.0269(7) 0.0224(7) -0.0008(7) -0.0007(7) 0.0014(6) P2 0.0226(7) 0.0235(7) 0.0324(8) -0.0003(7) 0.0010(8) -0.0009(7) O1 0.0229(18) 0.043(2) 0.033(2) 0.000(2) 0.0028(19) -0.0005(17) C1 0.033(3) 0.033(3) 0.023(3) 0.002(3) -0.008(3) 0.000(3) C2 0.044(4) 0.047(4) 0.022(3) -0.009(3) 0.005(3) 0.006(3) C3 0.049(4) 0.047(4) 0.034(3) 0.011(3) 0.018(3) 0.001(4) C4 0.030(3) 0.036(3) 0.042(4) -0.002(3) 0.011(3) 0.003(3) C5 0.029(3) 0.028(3) 0.021(3) 0.001(3) 0.001(2) -0.001(3) C6 0.033(3) 0.027(3) 0.037(4) 0.011(3) -0.007(3) 0.000(3) C7 0.037(4) 0.035(4) 0.039(4) 0.004(3) -0.011(3) 0.006(3) C8 0.022(3) 0.041(4) 0.051(4) 0.004(3) -0.005(3) -0.001(3) C9 0.030(3) 0.028(3) 0.030(3) 0.003(3) 0.006(3) 0.003(3) C10 0.049(4) 0.031(3) 0.030(4) -0.011(3) 0.008(3) 0.004(3) C11 0.027(3) 0.030(3) 0.047(4) 0.001(3) 0.002(3) -0.007(3) P3 0.0620(11) 0.0292(8) 0.0295(8) 0.0012(8) 0.0082(9) -0.0079(8) F1 0.203(6) 0.047(3) 0.087(4) 0.000(2) -0.062(4) -0.037(3) F2 0.085(3) 0.110(4) 0.102(4) 0.021(3) 0.053(3) 0.015(3) F3 0.115(4) 0.060(3) 0.063(3) 0.002(2) -0.038(3) -0.026(3) F4 0.090(3) 0.116(4) 0.128(5) 0.042(4) 0.058(3) 0.005(3) F5 0.060(3) 0.057(3) 0.062(3) 0.024(2) -0.016(2) 0.0028(19) F6 0.106(3) 0.044(2) 0.059(3) 0.016(2) -0.018(3) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.670(3) . ? P1 C5 1.815(5) . ? P1 C9 1.820(5) . ? P1 C1 1.833(5) . ? P1 P2 2.514(2) . ? P2 C11 1.805(5) . ? P2 C4 1.824(6) . ? P2 C8 1.830(6) . ? C1 C2 1.521(7) . ? C2 C3 1.527(7) . ? C3 C4 1.508(8) . ? C5 C6 1.532(7) . ? C6 C7 1.514(7) . ? C7 C8 1.526(7) . ? C9 C10 1.534(7) . ? C10 C11 1.524(7) . ? P3 F2 1.553(4) . ? P3 F3 1.566(4) . ? P3 F5 1.587(4) . ? P3 F1 1.602(4) . ? P3 F4 1.602(5) . ? P3 F6 1.640(4) . ? 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 C5 98.6(2) . . ? O1 P1 C9 88.9(2) . . ? C5 P1 C9 124.2(3) . . ? O1 P1 C1 95.8(2) . . ? C5 P1 C1 116.3(2) . . ? C9 P1 C1 117.7(3) . . ? O1 P1 P2 171.80(15) . . ? C5 P1 P2 86.84(17) . . ? C9 P1 P2 82.91(18) . . ? C1 P1 P2 87.28(18) . . ? C11 P2 C4 110.9(3) . . ? C11 P2 C8 106.7(3) . . ? C4 P2 C8 108.5(3) . . ? C11 P2 P1 96.00(18) . . ? C4 P2 P1 118.7(2) . . ? C8 P2 P1 114.78(19) . . ? C2 C1 P1 122.4(4) . . ? C1 C2 C3 116.5(5) . . ? C4 C3 C2 112.9(5) . . ? C3 C4 P2 110.0(4) . . ? C6 C5 P1 119.8(4) . . ? C7 C6 C5 116.7(5) . . ? C6 C7 C8 112.8(5) . . ? C7 C8 P2 110.7(4) . . ? C10 C9 P1 121.4(4) . . ? C11 C10 C9 112.0(4) . . ? C10 C11 P2 103.3(4) . . ? F2 P3 F3 90.7(3) . . ? F2 P3 F5 91.8(2) . . ? F3 P3 F5 92.0(2) . . ? F2 P3 F1 90.9(3) . . ? F3 P3 F1 177.9(3) . . ? F5 P3 F1 89.2(2) . . ? F2 P3 F4 176.9(3) . . ? F3 P3 F4 91.1(3) . . ? F5 P3 F4 90.7(2) . . ? F1 P3 F4 87.2(3) . . ? F2 P3 F6 91.3(2) . . ? F3 P3 F6 90.7(2) . . ? F5 P3 F6 175.9(2) . . ? F1 P3 F6 88.0(2) . . ? F4 P3 F6 86.2(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.634 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.081 #===END data_fffb _database_code_CSD 152498 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31 F3 O3 P2 S' _chemical_formula_weight 470.45 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.1709(12) _cell_length_b 21.173(3) _cell_length_c 8.6510(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2229.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 375 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max .6 _exptl_crystal_size_mid .56 _exptl_crystal_size_min .54 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13743 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4984 _reflns_number_gt 4655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0558P)^2^+0.2684P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2256 Friedel Pairs' _refine_ls_abs_structure_Flack 0.00(7) _refine_ls_number_reflns 4984 _refine_ls_number_parameters 263 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.60567(4) 0.35518(2) 0.31355(6) 0.01909(11) Uani 1 1 d . . . S1 S 0.16994(5) 0.35044(2) 0.49569(7) 0.02920(13) Uani 1 1 d . . . F1 F 0.28119(14) 0.44046(10) 0.3605(3) 0.0729(6) Uani 1 1 d . . . O1 O 0.24602(17) 0.30495(10) 0.4384(3) 0.0600(6) Uani 1 1 d . . . O2 O 0.05689(14) 0.33175(8) 0.4796(2) 0.0413(4) Uani 1 1 d . . . C2 C 0.73125(16) 0.32326(9) 0.2262(3) 0.0233(4) Uani 1 1 d . . . H2A H 0.7858 0.3177 0.3100 0.028 Uiso 1 1 calc R . . H2B H 0.7137 0.2806 0.1863 0.028 Uiso 1 1 calc R . . F2 F 0.16532(16) 0.39563(9) 0.21203(19) 0.0558(4) Uani 1 1 d . . . F3 F 0.11036(14) 0.46071(7) 0.3841(2) 0.0505(4) Uani 1 1 d . . . O3 O 0.19610(17) 0.38000(8) 0.6393(2) 0.0428(4) Uani 1 1 d . . . C3 C 0.78765(18) 0.35999(10) 0.0951(3) 0.0260(4) Uani 1 1 d . . . H3A H 0.7323 0.3875 0.0454 0.031 Uiso 1 1 calc R . . H3B H 0.8130 0.3293 0.0164 0.031 Uiso 1 1 calc R . . C4 C 0.88641(17) 0.40121(10) 0.1435(3) 0.0299(5) Uani 1 1 d . . . H4A H 0.9328 0.3769 0.2163 0.036 Uiso 1 1 calc R . . H4B H 0.9313 0.4105 0.0508 0.036 Uiso 1 1 calc R . . C5 C 0.85392(17) 0.46355(10) 0.2199(3) 0.0267(4) Uani 1 1 d . . . H5A H 0.8188 0.4913 0.1423 0.032 Uiso 1 1 calc R . . H5B H 0.9207 0.4851 0.2585 0.032 Uiso 1 1 calc R . . P6 P 0.75904(4) 0.45070(2) 0.38055(7) 0.01927(11) Uani 1 1 d . . . C7 C 0.69747(16) 0.52823(9) 0.4157(3) 0.0239(4) Uani 1 1 d . . . H7A H 0.6725 0.5311 0.5244 0.029 Uiso 1 1 calc R . . H7B H 0.7528 0.5617 0.3979 0.029 Uiso 1 1 calc R . . C8 C 0.59975(16) 0.53765(9) 0.3068(3) 0.0253(4) Uani 1 1 d . . . H8A H 0.5625 0.5777 0.3341 0.030 Uiso 1 1 calc R . . H8B H 0.6277 0.5419 0.1998 0.030 Uiso 1 1 calc R . . C9 C 0.51522(15) 0.48422(9) 0.3109(3) 0.0253(4) Uani 1 1 d . . . H9A H 0.4446 0.5012 0.2723 0.030 Uiso 1 1 calc R . . H9B H 0.5040 0.4720 0.4202 0.030 Uiso 1 1 calc R . . C10 C 0.54185(16) 0.42352(9) 0.2180(3) 0.0229(4) Uani 1 1 d . . . H10A H 0.5906 0.4360 0.1316 0.027 Uiso 1 1 calc R . . H10B H 0.4722 0.4087 0.1713 0.027 Uiso 1 1 calc R . . C11 C 0.59944(19) 0.35364(10) 0.5262(2) 0.0278(5) Uani 1 1 d . . . H11A H 0.5677 0.3944 0.5603 0.033 Uiso 1 1 calc R . . H11B H 0.5465 0.3203 0.5558 0.033 Uiso 1 1 calc R . . C12 C 0.7052(2) 0.34270(11) 0.6210(3) 0.0311(5) Uani 1 1 d . . . H12A H 0.6853 0.3178 0.7138 0.037 Uiso 1 1 calc R . . H12B H 0.7554 0.3164 0.5582 0.037 Uiso 1 1 calc R . . C13 C 0.76910(19) 0.40112(11) 0.6748(3) 0.0302(5) Uani 1 1 d . . . H13A H 0.8167 0.3889 0.7626 0.036 Uiso 1 1 calc R . . H13B H 0.7160 0.4329 0.7132 0.036 Uiso 1 1 calc R . . C14 C 0.84093(18) 0.43200(11) 0.5497(3) 0.0275(4) Uani 1 1 d . . . H14A H 0.9010 0.4028 0.5203 0.033 Uiso 1 1 calc R . . H14B H 0.8744 0.4711 0.5911 0.033 Uiso 1 1 calc R . . C15 C 0.50325(17) 0.29256(9) 0.2708(2) 0.0243(4) Uani 1 1 d . . . H15A H 0.5282 0.2531 0.3212 0.029 Uiso 1 1 calc R . . H15B H 0.4329 0.3048 0.3199 0.029 Uiso 1 1 calc R . . C16 C 0.48099(16) 0.27826(9) 0.1036(3) 0.0231(4) Uani 1 1 d . . . C17 C 0.39253(18) 0.30596(9) 0.0259(3) 0.0298(5) Uani 1 1 d . . . H17 H 0.3463 0.3348 0.0793 0.036 Uiso 1 1 calc R . . C18 C 0.3710(2) 0.29199(11) -0.1289(3) 0.0392(6) Uani 1 1 d . . . H18 H 0.3111 0.3117 -0.1802 0.047 Uiso 1 1 calc R . . C19 C 0.4364(2) 0.24964(12) -0.2075(3) 0.0410(6) Uani 1 1 d . . . H19 H 0.4223 0.2404 -0.3132 0.049 Uiso 1 1 calc R . . C20 C 0.52323(19) 0.22046(12) -0.1312(3) 0.0403(6) Uani 1 1 d . . . H20 H 0.5678 0.1906 -0.1841 0.048 Uiso 1 1 calc R . . C21 C 0.54459(18) 0.23485(11) 0.0212(3) 0.0306(5) Uani 1 1 d . . . H21 H 0.6043 0.2147 0.0717 0.037 Uiso 1 1 calc R . . C22 C 0.18230(18) 0.41476(11) 0.3567(3) 0.0323(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 0.0219(2) 0.0171(2) 0.0183(2) 0.00208(19) 0.0009(2) 0.00158(17) S1 0.0342(3) 0.0217(2) 0.0317(3) -0.0015(2) 0.0022(2) 0.0012(2) F1 0.0486(9) 0.0888(14) 0.0813(15) 0.0323(12) -0.0051(10) -0.0416(10) O1 0.0577(12) 0.0418(11) 0.0805(17) -0.0006(11) 0.0160(11) 0.0220(9) O2 0.0380(9) 0.0401(9) 0.0457(10) -0.0030(9) 0.0057(8) -0.0140(7) C2 0.0230(9) 0.0197(9) 0.0273(11) -0.0012(8) 0.0012(8) 0.0046(7) F2 0.0784(12) 0.0630(11) 0.0259(8) -0.0011(7) 0.0094(8) -0.0094(9) F3 0.0685(10) 0.0363(7) 0.0468(9) 0.0064(7) -0.0090(9) 0.0118(7) O3 0.0613(11) 0.0349(9) 0.0320(9) 0.0038(7) -0.0182(8) -0.0108(8) C3 0.0295(10) 0.0288(11) 0.0197(10) -0.0014(8) 0.0060(8) 0.0073(9) C4 0.0281(10) 0.0302(11) 0.0313(12) 0.0020(9) 0.0108(9) 0.0021(9) C5 0.0249(10) 0.0263(10) 0.0290(11) 0.0036(9) 0.0069(9) -0.0015(8) P6 0.0196(2) 0.0195(2) 0.0186(2) 0.00047(19) 0.0004(2) 0.00233(18) C7 0.0231(9) 0.0202(9) 0.0283(11) -0.0032(8) -0.0013(8) 0.0018(8) C8 0.0263(9) 0.0173(8) 0.0325(11) -0.0005(9) -0.0057(9) 0.0029(7) C9 0.0213(9) 0.0185(8) 0.0361(11) -0.0015(8) -0.0004(9) 0.0039(7) C10 0.0223(9) 0.0171(9) 0.0293(11) 0.0005(8) -0.0072(8) 0.0026(7) C11 0.0341(11) 0.0316(11) 0.0175(11) 0.0031(8) 0.0040(8) -0.0049(9) C12 0.0457(13) 0.0281(11) 0.0196(10) 0.0081(8) -0.0018(9) 0.0034(10) C13 0.0383(12) 0.0344(12) 0.0179(10) -0.0003(8) -0.0052(9) 0.0075(9) C14 0.0251(10) 0.0313(11) 0.0261(11) 0.0003(9) -0.0030(8) 0.0067(8) C15 0.0259(9) 0.0205(9) 0.0265(11) 0.0036(7) 0.0023(8) -0.0035(8) C16 0.0249(9) 0.0153(8) 0.0292(11) 0.0032(8) 0.0024(8) -0.0051(7) C17 0.0312(11) 0.0171(9) 0.0411(13) 0.0007(9) -0.0062(9) -0.0034(8) C18 0.0453(13) 0.0277(11) 0.0446(14) 0.0109(10) -0.0158(12) -0.0142(10) C19 0.0526(15) 0.0441(14) 0.0264(13) 0.0025(10) -0.0019(11) -0.0270(12) C20 0.0367(12) 0.0432(13) 0.0410(13) -0.0139(12) 0.0117(11) -0.0144(11) C21 0.0253(10) 0.0273(10) 0.0393(14) -0.0033(9) 0.0010(9) -0.0018(9) C22 0.0321(10) 0.0357(12) 0.0291(12) 0.0032(9) -0.0002(9) -0.0082(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 C2 1.834(2) . ? P1 C10 1.839(2) . ? P1 C11 1.842(2) . ? P1 C15 1.857(2) . ? S1 O1 1.425(2) . ? S1 O3 1.4270(19) . ? S1 O2 1.4384(18) . ? S1 C22 1.823(2) . ? F1 C22 1.321(3) . ? C2 C3 1.537(3) . ? F2 C22 1.332(3) . ? F3 C22 1.330(3) . ? C3 C4 1.543(3) . ? C4 C5 1.528(3) . ? C5 P6 1.827(2) . ? P6 C14 1.814(2) . ? P6 C7 1.830(2) . ? C7 C8 1.531(3) . ? C8 C9 1.529(3) . ? C9 C10 1.550(3) . ? C11 C12 1.544(3) . ? C12 C13 1.533(3) . ? C13 C14 1.537(3) . ? C15 C16 1.503(3) . ? C16 C21 1.397(3) . ? C16 C17 1.398(3) . ? C17 C18 1.397(4) . ? C18 C19 1.379(4) . ? C19 C20 1.391(4) . ? C20 C21 1.378(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C10 117.18(10) . . ? C2 P1 C11 116.07(10) . . ? C10 P1 C11 116.47(10) . . ? C2 P1 C15 102.37(10) . . ? C10 P1 C15 100.89(9) . . ? C11 P1 C15 99.12(10) . . ? O1 S1 O3 117.02(14) . . ? O1 S1 O2 113.70(13) . . ? O3 S1 O2 114.72(12) . . ? O1 S1 C22 102.82(13) . . ? O3 S1 C22 103.19(11) . . ? O2 S1 C22 102.76(11) . . ? C3 C2 P1 119.33(14) . . ? C2 C3 C4 115.70(19) . . ? C5 C4 C3 113.85(17) . . ? C4 C5 P6 111.33(15) . . ? C14 P6 C5 107.37(10) . . ? C14 P6 C7 106.65(10) . . ? C5 P6 C7 104.58(10) . . ? C8 C7 P6 109.43(14) . . ? C9 C8 C7 114.33(17) . . ? C8 C9 C10 117.43(17) . . ? C9 C10 P1 120.52(16) . . ? C12 C11 P1 119.96(16) . . ? C13 C12 C11 117.58(18) . . ? C12 C13 C14 114.73(19) . . ? C13 C14 P6 110.37(15) . . ? C16 C15 P1 117.16(14) . . ? C21 C16 C17 117.2(2) . . ? C21 C16 C15 121.59(19) . . ? C17 C16 C15 121.1(2) . . ? C18 C17 C16 121.1(2) . . ? C19 C18 C17 120.1(2) . . ? C18 C19 C20 119.6(2) . . ? C21 C20 C19 120.0(2) . . ? C20 C21 C16 121.9(2) . . ? F1 C22 F3 107.1(2) . . ? F1 C22 F2 106.8(2) . . ? F3 C22 F2 106.7(2) . . ? F1 C22 S1 111.51(18) . . ? F3 C22 S1 112.01(17) . . ? F2 C22 S1 112.33(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.100 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.052 #===END data_fftb _database_code_CSD 152499 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H29 F6 P3' _chemical_formula_weight 452.32 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 9.0947(3) _cell_length_b 18.9759(7) _cell_length_c 12.0451(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.2960(10) _cell_angle_gamma 90.00 _cell_volume 2078.21(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 112 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Irregular Blocks' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6672 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4037 _reflns_number_observed 3943 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0558P)^2^+0.2684P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 2393 Friedel Pairs' _refine_ls_abs_structure_Flack 0.02(7) _refine_ls_number_reflns 4037 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_obs 0.0327 _refine_ls_wR_factor_all 0.0865 _refine_ls_wR_factor_obs 0.0851 _refine_ls_goodness_of_fit_all 1.054 _refine_ls_goodness_of_fit_obs 1.050 _refine_ls_restrained_S_all 1.054 _refine_ls_restrained_S_obs 1.050 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.07505(5) 0.10341(2) 0.30188(4) 0.01895(11) Uani 1 d . . F1 F 0.3718(3) -0.1200(2) 0.1936(2) 0.0797(7) Uani 1 d . . C1 C 0.0181(2) 0.18519(11) 0.3700(2) 0.0236(4) Uani 1 d . . H1A H -0.0702(2) 0.20352(11) 0.3300(2) 0.028 Uiso 1 calc R . H1B H -0.0112(2) 0.17363(11) 0.4465(2) 0.028 Uiso 1 calc R . P2 P 0.16254(6) 0.20861(3) 0.15936(4) 0.02402(13) Uani 1 d . . F2 F 0.1613(3) -0.05988(9) 0.1813(2) 0.0694(6) Uani 1 d . . C2 C 0.1344(3) 0.24468(11) 0.3763(2) 0.0280(4) Uani 1 d . . H2A H 0.1012(3) 0.28130(11) 0.4287(2) 0.034 Uiso 1 calc R . H2B H 0.2281(3) 0.22505(11) 0.4062(2) 0.034 Uiso 1 calc R . P3 P 0.20677(6) -0.13671(3) 0.22213(5) 0.02668(13) Uani 1 d . . F3 F 0.2539(3) -0.21246(9) 0.2632(2) 0.0795(8) Uani 1 d . . C3 C 0.1619(3) 0.27900(11) 0.2632(2) 0.0324(5) Uani 1 d . . H3A H 0.2575(3) 0.30394(11) 0.2648(2) 0.039 Uiso 1 calc R . H3B H 0.0833(3) 0.31352(11) 0.2450(2) 0.039 Uiso 1 calc R . F4 F 0.1762(3) -0.16639(13) 0.1011(2) 0.0712(7) Uani 1 d . . C4 C 0.2726(2) 0.08348(11) 0.3096(2) 0.0265(4) Uani 1 d . . H4A H 0.3167(2) 0.11585(11) 0.3656(2) 0.032 Uiso 1 calc R . H4B H 0.2822(2) 0.03531(11) 0.3405(2) 0.032 Uiso 1 calc R . F5 F 0.0408(2) -0.1510(2) 0.2518(2) 0.0791(7) Uani 1 d . . C5 C 0.3710(3) 0.08658(14) 0.2071(2) 0.0369(6) Uani 1 d . . H5A H 0.3113(3) 0.07199(14) 0.1414(2) 0.044 Uiso 1 calc R . H5B H 0.4507(3) 0.05147(14) 0.2173(2) 0.044 Uiso 1 calc R . F6 F 0.2357(2) -0.10572(10) 0.34497(15) 0.0506(4) Uani 1 d . . C6 C 0.4419(3) 0.1585(2) 0.1815(3) 0.0449(7) Uani 1 d . . H6A H 0.4599(3) 0.1842(2) 0.2521(3) 0.054 Uiso 1 calc R . H6B H 0.5381(3) 0.1505(2) 0.1469(3) 0.054 Uiso 1 calc R . C7 C 0.3459(3) 0.20394(15) 0.1041(2) 0.0375(6) Uani 1 d . . H7A H 0.3419(3) 0.18302(15) 0.0288(2) 0.045 Uiso 1 calc R . H7B H 0.3881(3) 0.25187(15) 0.0987(2) 0.045 Uiso 1 calc R . C8 C -0.0269(3) 0.07462(11) 0.1775(2) 0.0253(4) Uani 1 d . . H8A H 0.0455(3) 0.05504(11) 0.1257(2) 0.030 Uiso 1 calc R . H8B H -0.0910(3) 0.03511(11) 0.1997(2) 0.030 Uiso 1 calc R . C9 C -0.1239(2) 0.12710(12) 0.1110(2) 0.0284(5) Uani 1 d . . H9A H -0.2116(2) 0.10159(12) 0.0820(2) 0.034 Uiso 1 calc R . H9B H -0.1586(2) 0.16377(12) 0.1627(2) 0.034 Uiso 1 calc R . C10 C -0.0503(3) 0.16369(12) 0.0136(2) 0.0329(5) Uani 1 d . . H10A H -0.1268(3) 0.17581(12) -0.0431(2) 0.039 Uiso 1 calc R . H10B H 0.0186(3) 0.13018(12) -0.0208(2) 0.039 Uiso 1 calc R . C11 C 0.0343(3) 0.23094(12) 0.0457(2) 0.0330(5) Uani 1 d . . H11A H -0.0349(3) 0.26794(12) 0.0697(2) 0.040 Uiso 1 calc R . H11B H 0.0887(3) 0.24888(12) -0.0187(2) 0.040 Uiso 1 calc R . C12 C 0.0181(2) 0.03600(11) 0.4050(2) 0.0245(4) Uani 1 d . . H12A H 0.0500(2) -0.01065(11) 0.3777(2) 0.029 Uiso 1 calc R . H12B H 0.0736(2) 0.04519(11) 0.4752(2) 0.029 Uiso 1 calc R . C13 C -0.1424(2) 0.03059(11) 0.4323(2) 0.0242(4) Uani 1 d . . C14 C -0.2005(3) 0.06892(12) 0.5199(2) 0.0304(5) Uani 1 d . . H14 H -0.1389(3) 0.10029(12) 0.5612(2) 0.037 Uiso 1 calc R . C15 C -0.3477(3) 0.06176(15) 0.5476(2) 0.0404(6) Uani 1 d . . H15 H -0.3855(3) 0.08794(15) 0.6078(2) 0.048 Uiso 1 calc R . C16 C -0.4392(3) 0.0166(2) 0.4876(2) 0.0442(7) Uani 1 d . . H16 H -0.5399(3) 0.0125(2) 0.5058(2) 0.053 Uiso 1 calc R . C17 C -0.3834(3) -0.0228(2) 0.4010(2) 0.0394(6) Uani 1 d . . H17 H -0.4452(3) -0.0548(2) 0.3610(2) 0.047 Uiso 1 calc R . C18 C -0.2362(3) -0.01531(12) 0.3729(2) 0.0303(5) Uani 1 d . . H18 H -0.1989(3) -0.04165(12) 0.3126(2) 0.036 Uiso 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 0.0190(2) 0.0192(2) 0.0187(2) -0.0006(2) 0.0023(2) 0.0014(2) F1 0.0408(12) 0.118(2) 0.081(2) -0.0010(14) 0.0223(11) -0.0042(12) C1 0.0254(10) 0.0228(9) 0.0228(10) -0.0042(7) 0.0042(8) -0.0011(7) P2 0.0268(3) 0.0237(2) 0.0217(2) 0.0022(2) 0.0031(2) -0.0003(2) F2 0.112(2) 0.0387(9) 0.0565(12) 0.0054(8) -0.0167(12) 0.0237(11) C2 0.0351(12) 0.0241(9) 0.0248(10) -0.0040(8) -0.0001(9) -0.0045(8) P3 0.0278(3) 0.0258(3) 0.0264(3) -0.0018(2) 0.0001(2) 0.0073(2) F3 0.113(2) 0.0314(9) 0.093(2) 0.0075(10) -0.026(2) 0.0172(10) C3 0.0454(15) 0.0217(10) 0.0300(12) 0.0011(8) 0.0028(10) -0.0058(9) F4 0.097(2) 0.0775(14) 0.0381(10) -0.0253(9) -0.0114(11) 0.0198(12) C4 0.0201(10) 0.0276(10) 0.0317(12) 0.0045(8) 0.0017(9) 0.0051(8) F5 0.0350(11) 0.123(2) 0.079(2) -0.0112(15) 0.0066(11) -0.0177(12) C5 0.0265(12) 0.0430(13) 0.0417(15) 0.0101(11) 0.0114(11) 0.0116(10) F6 0.0625(12) 0.0574(10) 0.0313(8) -0.0098(7) -0.0072(8) 0.0100(8) C6 0.0223(12) 0.060(2) 0.053(2) 0.0175(13) 0.0085(12) -0.0026(11) C7 0.0321(13) 0.0445(13) 0.0364(13) 0.0095(10) 0.0115(11) -0.0037(10) C8 0.0312(11) 0.0244(10) 0.0203(9) -0.0041(7) -0.0008(8) -0.0038(8) C9 0.0226(11) 0.0342(11) 0.0281(11) -0.0075(9) -0.0039(9) 0.0055(8) C10 0.0433(15) 0.0337(11) 0.0213(10) -0.0022(8) -0.0067(10) 0.0108(10) C11 0.0425(14) 0.0316(11) 0.0247(11) 0.0048(8) -0.0018(10) 0.0071(10) C12 0.0247(11) 0.0243(9) 0.0244(10) 0.0018(7) 0.0028(8) 0.0024(8) C13 0.0248(10) 0.0249(9) 0.0231(10) 0.0041(7) 0.0037(8) -0.0009(8) C14 0.0355(13) 0.0291(10) 0.0271(11) 0.0011(8) 0.0090(10) -0.0003(9) C15 0.0370(14) 0.0451(14) 0.0397(14) 0.0076(11) 0.0137(12) 0.0102(11) C16 0.0267(13) 0.061(2) 0.045(2) 0.0209(13) 0.0084(11) 0.0016(12) C17 0.0328(13) 0.0481(14) 0.0369(13) 0.0146(10) -0.0064(11) -0.0115(11) C18 0.0315(12) 0.0314(11) 0.0282(11) 0.0027(8) 0.0027(9) -0.0027(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 C8 1.828(2) . ? P1 C1 1.836(2) . ? P1 C4 1.836(2) . ? P1 C12 1.865(2) . ? F1 P3 1.579(2) . ? C1 C2 1.548(3) . ? P2 C7 1.811(3) . ? P2 C11 1.828(3) . ? P2 C3 1.830(2) . ? F2 P3 1.590(2) . ? C2 C3 1.536(3) . ? P3 F3 1.577(2) . ? P3 F4 1.582(2) . ? P3 F5 1.582(2) . ? P3 F6 1.608(2) . ? C4 C5 1.542(3) . ? C5 C6 1.543(4) . ? C6 C7 1.530(4) . ? C8 C9 1.542(3) . ? C9 C10 1.531(3) . ? C10 C11 1.535(4) . ? C12 C13 1.507(3) . ? C13 C14 1.395(3) . ? C13 C18 1.404(3) . ? C14 C15 1.394(3) . ? C15 C16 1.387(5) . ? C16 C17 1.389(4) . ? C17 C18 1.395(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 C8 P1 C1 118.41(10) . . ? C8 P1 C4 117.25(10) . . ? C1 P1 C4 115.93(11) . . ? C8 P1 C12 101.40(10) . . ? C1 P1 C12 101.34(9) . . ? C4 P1 C12 96.38(10) . . ? C2 C1 P1 116.05(15) . . ? C7 P2 C11 108.25(13) . . ? C7 P2 C3 107.71(13) . . ? C11 P2 C3 109.30(12) . . ? C3 C2 C1 112.9(2) . . ? F3 P3 F1 89.9(2) . . ? F3 P3 F4 90.34(14) . . ? F1 P3 F4 91.10(14) . . ? F3 P3 F5 91.5(2) . . ? F1 P3 F5 178.2(2) . . ? F4 P3 F5 89.91(14) . . ? F3 P3 F2 179.2(2) . . ? F1 P3 F2 89.44(15) . . ? F4 P3 F2 90.14(12) . . ? F5 P3 F2 89.1(2) . . ? F3 P3 F6 90.38(13) . . ? F1 P3 F6 89.44(13) . . ? F4 P3 F6 179.10(12) . . ? F5 P3 F6 89.54(12) . . ? F2 P3 F6 89.14(10) . . ? C2 C3 P2 107.46(14) . . ? C5 C4 P1 122.5(2) . . ? C4 C5 C6 116.5(2) . . ? C7 C6 C5 112.7(2) . . ? C6 C7 P2 108.7(2) . . ? C9 C8 P1 120.42(15) . . ? C10 C9 C8 115.9(2) . . ? C9 C10 C11 114.1(2) . . ? C10 C11 P2 107.7(2) . . ? C13 C12 P1 118.47(15) . . ? C14 C13 C18 118.2(2) . . ? C14 C13 C12 120.9(2) . . ? C18 C13 C12 120.8(2) . . ? C15 C14 C13 120.8(2) . . ? C16 C15 C14 120.3(2) . . ? C15 C16 C17 120.0(2) . . ? C16 C17 C18 119.7(3) . . ? C17 C18 C13 121.0(2) . . ? 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 C8 P1 C1 C2 -119.0(2) . . . . ? C4 P1 C1 C2 28.3(2) . . . . ? C12 P1 C1 C2 131.2(2) . . . . ? P1 C1 C2 C3 71.5(2) . . . . ? C1 C2 C3 P2 -40.3(2) . . . . ? C7 P2 C3 C2 -115.0(2) . . . . ? C11 P2 C3 C2 127.6(2) . . . . ? C8 P1 C4 C5 37.2(2) . . . . ? C1 P1 C4 C5 -110.5(2) . . . . ? C12 P1 C4 C5 143.6(2) . . . . ? P1 C4 C5 C6 88.6(3) . . . . ? C4 C5 C6 C7 -90.3(3) . . . . ? C5 C6 C7 P2 51.3(3) . . . . ? C11 P2 C7 C6 -157.8(2) . . . . ? C3 P2 C7 C6 84.2(2) . . . . ? C1 P1 C8 C9 18.6(2) . . . . ? C4 P1 C8 C9 -128.3(2) . . . . ? C12 P1 C8 C9 128.4(2) . . . . ? P1 C8 C9 C10 93.7(2) . . . . ? C8 C9 C10 C11 -86.5(2) . . . . ? C9 C10 C11 P2 53.2(2) . . . . ? C7 P2 C11 C10 104.8(2) . . . . ? C3 P2 C11 C10 -138.1(2) . . . . ? C8 P1 C12 C13 -61.4(2) . . . . ? C1 P1 C12 C13 61.0(2) . . . . ? C4 P1 C12 C13 179.1(2) . . . . ? P1 C12 C13 C14 -91.3(2) . . . . ? P1 C12 C13 C18 91.3(2) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? C12 C13 C14 C15 -177.5(2) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C15 C16 C17 1.3(4) . . . . ? C15 C16 C17 C18 -1.7(4) . . . . ? C16 C17 C18 C13 1.2(4) . . . . ? C14 C13 C18 C17 -0.4(3) . . . . ? C12 C13 C18 C17 177.1(2) . . . . ? _refine_diff_density_max 0.389 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.052