# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ljh21_0m _database_code_depnum_ccdc_archive 'CCDC 904900' #TrackingRef 'All-CIFs-4-structures-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C111 H57 B2 F44 P4' _chemical_formula_weight 2372.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7377(6) _cell_length_b 13.3608(8) _cell_length_c 18.5330(11) _cell_angle_alpha 85.615(3) _cell_angle_beta 89.546(4) _cell_angle_gamma 71.427(3) _cell_volume 2512.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9251 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 28.42 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1189 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7080 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47216 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.49 _reflns_number_total 12691 _reflns_number_gt 9213 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0874P)^2^+1.7605P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12691 _refine_ls_number_parameters 739 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1692 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.049 _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 0.46041(5) -0.09575(4) 0.26493(3) 0.01946(13) Uani 1 1 d . . . P2 P 0.19024(6) 0.39775(5) 0.32259(3) 0.02502(14) Uani 1 1 d . . . F1 F 0.32129(14) 0.41879(11) 0.28565(8) 0.0323(3) Uani 1 1 d . . . F2 F 0.06671(14) 0.36620(12) 0.36140(8) 0.0339(3) Uani 1 1 d . . . F3 F 0.27828(16) 0.30258(11) 0.17930(8) 0.0366(4) Uani 1 1 d . . . F4 F 0.38787(16) 0.10387(11) 0.15266(7) 0.0367(4) Uani 1 1 d . . . F5 F 0.36007(16) -0.00108(11) 0.40019(7) 0.0341(3) Uani 1 1 d . . . F6 F 0.25744(17) 0.20000(12) 0.42732(8) 0.0387(4) Uani 1 1 d . . . F7 F 0.67095(13) 0.08789(11) 0.23334(7) 0.0279(3) Uani 1 1 d . . . F8 F 0.93414(18) 0.26595(14) 0.18318(12) 0.0578(5) Uani 1 1 d . . . F9 F 1.12471(19) 0.20372(17) 0.08674(14) 0.0704(7) Uani 1 1 d . . . F10 F 1.18228(18) 0.00876(17) 0.03532(10) 0.0602(6) Uani 1 1 d . . . F11 F 1.04754(18) -0.12194(14) 0.08321(11) 0.0538(5) Uani 1 1 d . . . F12 F 0.85956(15) -0.06342(12) 0.17883(9) 0.0389(4) Uani 1 1 d . . . F13 F 0.7121(2) 0.36526(13) 0.30355(9) 0.0497(5) Uani 1 1 d . . . F14 F 0.5518(2) 0.55078(14) 0.25052(11) 0.0605(5) Uani 1 1 d . . . F15 F 0.4179(2) 0.56866(15) 0.12361(12) 0.0639(6) Uani 1 1 d . . . F16 F 0.4520(2) 0.39310(17) 0.05017(11) 0.0706(6) Uani 1 1 d . . . F17 F 0.60931(18) 0.20515(13) 0.10315(9) 0.0486(4) Uani 1 1 d . . . F18 F 1.02861(15) 0.10620(15) 0.30825(9) 0.0455(4) Uani 1 1 d . . . F19 F 1.07433(19) 0.09524(17) 0.44869(11) 0.0625(6) Uani 1 1 d . . . F20 F 0.8766(2) 0.13050(18) 0.54388(10) 0.0700(6) Uani 1 1 d . . . F21 F 0.6228(2) 0.17866(16) 0.49404(9) 0.0555(5) Uani 1 1 d . . . F22 F 0.57304(14) 0.18985(13) 0.35289(8) 0.0356(3) Uani 1 1 d . . . B1 B 0.7547(3) 0.1518(2) 0.23687(14) 0.0240(5) Uani 1 1 d . . . C1 C 0.4970(2) -0.12277(18) 0.17295(12) 0.0228(4) Uani 1 1 d . . . C2 C 0.5950(2) -0.0891(2) 0.13969(14) 0.0308(5) Uani 1 1 d . . . H2A H 0.6382 -0.0499 0.1648 0.037 Uiso 1 1 calc R . . C3 C 0.6283(3) -0.1136(2) 0.06937(15) 0.0385(6) Uani 1 1 d . . . H3A H 0.6947 -0.0907 0.0460 0.046 Uiso 1 1 calc R . . C4 C 0.5658(3) -0.1713(2) 0.03286(15) 0.0419(7) Uani 1 1 d . . . H4A H 0.5893 -0.1878 -0.0154 0.050 Uiso 1 1 calc R . . C5 C 0.4700(3) -0.2045(3) 0.06632(15) 0.0465(7) Uani 1 1 d . . . H5A H 0.4273 -0.2438 0.0410 0.056 Uiso 1 1 calc R . . C6 C 0.4347(3) -0.1813(2) 0.13675(14) 0.0352(6) Uani 1 1 d . . . H6A H 0.3688 -0.2051 0.1599 0.042 Uiso 1 1 calc R . . C7 C 0.3473(2) -0.16196(17) 0.29694(12) 0.0212(4) Uani 1 1 d . . . C8 C 0.2162(2) -0.1190(2) 0.27450(13) 0.0286(5) Uani 1 1 d . . . H8A H 0.1871 -0.0529 0.2465 0.034 Uiso 1 1 calc R . . C9 C 0.1287(3) -0.1730(2) 0.29323(14) 0.0337(6) Uani 1 1 d . . . H9A H 0.0392 -0.1441 0.2782 0.040 Uiso 1 1 calc R . . C10 C 0.1719(3) -0.2693(2) 0.33382(14) 0.0336(6) Uani 1 1 d . . . H10A H 0.1119 -0.3067 0.3460 0.040 Uiso 1 1 calc R . . C11 C 0.3012(3) -0.3114(2) 0.35674(15) 0.0336(6) Uani 1 1 d . . . H11A H 0.3298 -0.3774 0.3849 0.040 Uiso 1 1 calc R . . C12 C 0.3896(2) -0.25746(19) 0.33874(13) 0.0283(5) Uani 1 1 d . . . H12A H 0.4785 -0.2858 0.3550 0.034 Uiso 1 1 calc R . . C13 C 0.6109(2) -0.14133(18) 0.31662(12) 0.0224(4) Uani 1 1 d . . . C14 C 0.6929(2) -0.2437(2) 0.30817(15) 0.0366(6) Uani 1 1 d . . . H14A H 0.6714 -0.2847 0.2735 0.044 Uiso 1 1 calc R . . C15 C 0.8059(3) -0.2859(2) 0.35046(17) 0.0441(7) Uani 1 1 d . . . H15A H 0.8609 -0.3565 0.3456 0.053 Uiso 1 1 calc R . . C16 C 0.8388(3) -0.2253(2) 0.39981(15) 0.0382(6) Uani 1 1 d . . . H16A H 0.9157 -0.2546 0.4293 0.046 Uiso 1 1 calc R . . C17 C 0.7601(3) -0.1227(2) 0.40606(15) 0.0373(6) Uani 1 1 d . . . H17A H 0.7843 -0.0808 0.4391 0.045 Uiso 1 1 calc R . . C18 C 0.6461(3) -0.0800(2) 0.36471(13) 0.0305(5) Uani 1 1 d . . . H18A H 0.5922 -0.0090 0.3692 0.037 Uiso 1 1 calc R . . C19 C 0.3811(2) 0.04341(17) 0.27596(12) 0.0205(4) Uani 1 1 d . . . C20 C 0.3572(2) 0.12439(18) 0.22116(12) 0.0239(5) Uani 1 1 d . . . C21 C 0.2990(2) 0.22924(18) 0.23521(12) 0.0241(5) Uani 1 1 d . . . C22 C 0.2618(2) 0.25889(17) 0.30398(12) 0.0228(4) Uani 1 1 d . . . C23 C 0.2855(2) 0.17809(19) 0.35876(12) 0.0255(5) Uani 1 1 d . . . C24 C 0.3415(2) 0.07341(18) 0.34475(12) 0.0248(5) Uani 1 1 d . . . C25 C 0.0804(3) 0.48963(19) 0.25685(14) 0.0316(5) Uani 1 1 d . . . C26 C -0.0444(3) 0.4825(2) 0.24295(17) 0.0427(7) Uani 1 1 d . . . H26A H -0.0719 0.4286 0.2680 0.051 Uiso 1 1 calc R . . C27 C -0.1274(4) 0.5539(3) 0.1927(2) 0.0599(10) Uani 1 1 d . . . H27A H -0.2109 0.5476 0.1822 0.072 Uiso 1 1 calc R . . C28 C -0.0901(4) 0.6341(3) 0.1578(2) 0.0679(12) Uani 1 1 d . . . H28A H -0.1491 0.6840 0.1245 0.081 Uiso 1 1 calc R . . C29 C 0.0303(4) 0.6424(3) 0.17067(19) 0.0621(10) Uani 1 1 d . . . H29A H 0.0547 0.6985 0.1465 0.075 Uiso 1 1 calc R . . C30 C 0.1189(3) 0.5689(2) 0.21941(16) 0.0442(7) Uani 1 1 d . . . H30A H 0.2045 0.5732 0.2268 0.053 Uiso 1 1 calc R . . C31 C 0.2314(2) 0.43855(18) 0.40749(13) 0.0265(5) Uani 1 1 d . . . C32 C 0.1348(3) 0.5074(2) 0.44677(14) 0.0303(5) Uani 1 1 d . . . H32A H 0.0462 0.5319 0.4298 0.036 Uiso 1 1 calc R . . C33 C 0.1691(3) 0.5401(2) 0.51149(16) 0.0423(7) Uani 1 1 d . . . H33A H 0.1045 0.5899 0.5373 0.051 Uiso 1 1 calc R . . C34 C 0.2956(4) 0.5008(3) 0.53773(16) 0.0481(8) Uani 1 1 d . . . H34A H 0.3180 0.5222 0.5822 0.058 Uiso 1 1 calc R . . C35 C 0.3906(3) 0.4303(3) 0.49982(17) 0.0448(7) Uani 1 1 d . . . H35A H 0.4777 0.4019 0.5190 0.054 Uiso 1 1 calc R . . C36 C 0.3601(3) 0.4008(2) 0.43407(15) 0.0351(6) Uani 1 1 d . . . H36A H 0.4269 0.3547 0.4071 0.042 Uiso 1 1 calc R . . C37 C 0.8800(2) 0.10814(19) 0.18307(12) 0.0252(5) Uani 1 1 d . . . C38 C 0.9560(3) 0.1700(2) 0.15791(16) 0.0358(6) Uani 1 1 d . . . C39 C 1.0560(3) 0.1392(2) 0.10874(17) 0.0424(7) Uani 1 1 d . . . C40 C 1.0861(3) 0.0410(2) 0.08308(15) 0.0395(6) Uani 1 1 d . . . C41 C 1.0171(3) -0.0249(2) 0.10729(14) 0.0344(6) Uani 1 1 d . . . C42 C 0.9175(2) 0.00918(19) 0.15662(13) 0.0259(5) Uani 1 1 d . . . C43 C 0.6661(2) 0.27352(18) 0.20716(12) 0.0252(5) Uani 1 1 d . . . C44 C 0.6479(3) 0.3664(2) 0.24103(13) 0.0316(5) Uani 1 1 d . . . C45 C 0.5666(3) 0.4645(2) 0.21418(16) 0.0384(6) Uani 1 1 d . . . C46 C 0.4999(3) 0.4737(2) 0.14999(17) 0.0416(7) Uani 1 1 d . . . C47 C 0.5151(3) 0.3852(2) 0.11359(16) 0.0418(7) Uani 1 1 d . . . C48 C 0.5971(3) 0.2887(2) 0.14237(14) 0.0333(6) Uani 1 1 d . . . C49 C 0.7975(2) 0.14619(19) 0.32234(13) 0.0261(5) Uani 1 1 d . . . C50 C 0.9224(2) 0.1237(2) 0.35130(14) 0.0326(5) Uani 1 1 d . . . C51 C 0.9497(3) 0.1181(2) 0.42444(16) 0.0420(7) Uani 1 1 d . . . C52 C 0.8500(3) 0.1359(2) 0.47260(15) 0.0454(7) Uani 1 1 d . . . C53 C 0.7231(3) 0.1594(2) 0.44748(14) 0.0377(6) Uani 1 1 d . . . C54 C 0.7006(2) 0.16373(19) 0.37408(13) 0.0290(5) Uani 1 1 d . . . C101 C 0.0157(5) 0.5364(5) -0.0087(3) 0.052(2) Uani 0.50 1 d PD . . H10D H -0.0348 0.5971 0.0184 0.062 Uiso 0.50 1 calc PR . . H10E H -0.0035 0.5562 -0.0610 0.062 Uiso 0.50 1 calc PR . . C102 C 0.1561(6) 0.5129(6) 0.0056(4) 0.058(2) Uani 0.50 1 d PD . . H10B H 0.1765 0.4950 0.0579 0.070 Uiso 0.50 1 calc PR . . H10C H 0.2080 0.4527 -0.0214 0.070 Uiso 0.50 1 calc PR . . C103 C 0.1843(9) 0.6067(8) -0.0184(4) 0.102(4) Uani 0.50 1 d PD . . H10F H 0.2775 0.5967 -0.0093 0.153 Uiso 0.50 1 calc PR . . H10G H 0.1303 0.6658 0.0080 0.153 Uiso 0.50 1 calc PR . . H10H H 0.1646 0.6226 -0.0703 0.153 Uiso 0.50 1 calc PR . . 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 0.0201(3) 0.0210(3) 0.0182(3) -0.0036(2) -0.0014(2) -0.0074(2) P2 0.0248(3) 0.0226(3) 0.0287(3) -0.0050(2) 0.0030(2) -0.0084(2) F1 0.0325(8) 0.0311(7) 0.0364(8) -0.0030(6) 0.0080(6) -0.0147(6) F2 0.0300(8) 0.0346(8) 0.0407(8) -0.0115(6) 0.0074(6) -0.0133(6) F3 0.0525(10) 0.0260(7) 0.0243(7) 0.0043(6) -0.0003(7) -0.0040(7) F4 0.0538(10) 0.0309(8) 0.0163(7) -0.0007(5) 0.0018(6) -0.0009(7) F5 0.0564(10) 0.0257(7) 0.0212(7) 0.0003(5) 0.0082(6) -0.0151(7) F6 0.0642(11) 0.0297(8) 0.0241(7) -0.0083(6) 0.0158(7) -0.0167(7) F7 0.0263(7) 0.0325(7) 0.0302(7) -0.0082(6) 0.0015(6) -0.0156(6) F8 0.0458(10) 0.0371(9) 0.1008(16) -0.0201(10) 0.0176(10) -0.0246(8) F9 0.0451(11) 0.0587(13) 0.1083(18) 0.0171(12) 0.0254(11) -0.0239(10) F10 0.0460(11) 0.0692(13) 0.0516(11) 0.0053(9) 0.0268(9) -0.0020(9) F11 0.0526(11) 0.0425(10) 0.0612(12) -0.0232(8) 0.0150(9) -0.0039(8) F12 0.0311(8) 0.0273(7) 0.0602(10) -0.0056(7) 0.0060(7) -0.0117(6) F13 0.0775(13) 0.0385(9) 0.0382(9) -0.0126(7) -0.0140(9) -0.0231(9) F14 0.0883(15) 0.0302(9) 0.0615(12) -0.0185(8) 0.0101(11) -0.0136(9) F15 0.0653(13) 0.0368(10) 0.0739(14) 0.0074(9) -0.0045(11) 0.0032(9) F16 0.0824(15) 0.0557(12) 0.0582(12) 0.0006(10) -0.0407(11) -0.0002(11) F17 0.0638(11) 0.0416(9) 0.0360(9) -0.0143(7) -0.0218(8) -0.0073(8) F18 0.0233(8) 0.0639(11) 0.0505(10) -0.0142(8) -0.0042(7) -0.0131(7) F19 0.0500(11) 0.0742(14) 0.0620(12) -0.0113(10) -0.0338(9) -0.0158(10) F20 0.0952(16) 0.0724(14) 0.0295(9) -0.0105(9) -0.0245(10) -0.0065(12) F21 0.0692(13) 0.0603(12) 0.0270(8) -0.0043(8) 0.0126(8) -0.0065(10) F22 0.0249(7) 0.0458(9) 0.0336(8) -0.0052(7) 0.0037(6) -0.0072(6) B1 0.0228(12) 0.0292(13) 0.0226(12) -0.0056(10) -0.0004(10) -0.0112(10) C1 0.0243(11) 0.0244(11) 0.0199(10) -0.0036(8) -0.0010(8) -0.0077(9) C2 0.0297(12) 0.0363(13) 0.0301(13) -0.0082(10) 0.0038(10) -0.0145(10) C3 0.0399(15) 0.0473(16) 0.0322(14) -0.0048(11) 0.0119(11) -0.0192(13) C4 0.0577(18) 0.0491(17) 0.0217(12) -0.0069(11) 0.0069(12) -0.0200(14) C5 0.068(2) 0.0596(19) 0.0263(14) -0.0156(13) 0.0042(13) -0.0373(17) C6 0.0472(16) 0.0446(15) 0.0242(12) -0.0084(10) 0.0032(11) -0.0279(13) C7 0.0235(11) 0.0223(10) 0.0199(10) -0.0042(8) 0.0012(8) -0.0096(8) C8 0.0272(12) 0.0289(12) 0.0289(12) 0.0027(9) -0.0037(9) -0.0087(10) C9 0.0248(12) 0.0418(14) 0.0365(14) 0.0018(11) -0.0060(10) -0.0142(11) C10 0.0355(14) 0.0358(13) 0.0367(14) -0.0038(11) 0.0045(11) -0.0215(11) C11 0.0367(14) 0.0265(12) 0.0388(14) 0.0043(10) -0.0015(11) -0.0132(11) C12 0.0258(12) 0.0254(11) 0.0327(13) 0.0001(9) -0.0030(10) -0.0073(9) C13 0.0210(10) 0.0258(11) 0.0213(10) -0.0007(8) -0.0016(8) -0.0088(9) C14 0.0257(12) 0.0388(14) 0.0424(15) -0.0167(12) -0.0042(11) -0.0029(11) C15 0.0274(13) 0.0418(16) 0.0545(18) -0.0151(13) -0.0078(12) 0.0037(11) C16 0.0264(13) 0.0485(16) 0.0356(14) -0.0035(12) -0.0092(11) -0.0059(11) C17 0.0376(14) 0.0399(14) 0.0356(14) -0.0052(11) -0.0152(11) -0.0130(12) C18 0.0339(13) 0.0264(12) 0.0305(13) -0.0005(9) -0.0110(10) -0.0087(10) C19 0.0215(10) 0.0209(10) 0.0209(10) -0.0028(8) -0.0006(8) -0.0089(8) C20 0.0249(11) 0.0275(11) 0.0181(10) -0.0029(8) -0.0004(8) -0.0063(9) C21 0.0246(11) 0.0232(11) 0.0228(11) 0.0013(8) -0.0020(9) -0.0061(9) C22 0.0213(11) 0.0215(10) 0.0272(11) -0.0049(8) 0.0025(9) -0.0087(8) C23 0.0327(12) 0.0271(11) 0.0204(11) -0.0062(8) 0.0073(9) -0.0137(10) C24 0.0308(12) 0.0252(11) 0.0208(11) -0.0001(8) 0.0030(9) -0.0128(9) C25 0.0346(13) 0.0263(12) 0.0317(13) -0.0101(10) -0.0008(10) -0.0047(10) C26 0.0345(15) 0.0458(16) 0.0449(17) -0.0164(13) -0.0041(12) -0.0056(12) C27 0.0469(19) 0.066(2) 0.054(2) -0.0195(18) -0.0156(16) 0.0036(17) C28 0.075(3) 0.056(2) 0.051(2) -0.0118(17) -0.0231(19) 0.0119(19) C29 0.095(3) 0.0357(17) 0.0471(19) 0.0036(14) -0.0107(19) -0.0105(18) C30 0.0570(19) 0.0337(14) 0.0404(16) -0.0034(12) -0.0059(14) -0.0120(13) C31 0.0305(12) 0.0221(11) 0.0284(12) -0.0026(9) 0.0016(9) -0.0105(9) C32 0.0326(13) 0.0294(12) 0.0324(13) -0.0072(10) 0.0085(10) -0.0139(10) C33 0.0559(18) 0.0413(15) 0.0388(15) -0.0160(12) 0.0169(13) -0.0259(14) C34 0.070(2) 0.0544(18) 0.0313(15) -0.0072(13) -0.0035(14) -0.0350(17) C35 0.0463(17) 0.0464(17) 0.0455(17) 0.0023(13) -0.0142(14) -0.0209(14) C36 0.0325(13) 0.0297(12) 0.0410(15) -0.0026(11) -0.0029(11) -0.0068(10) C37 0.0242(11) 0.0301(12) 0.0229(11) -0.0032(9) -0.0013(9) -0.0105(9) C38 0.0326(13) 0.0308(13) 0.0465(16) -0.0035(11) 0.0047(12) -0.0137(11) C39 0.0306(14) 0.0423(16) 0.0534(18) 0.0120(13) 0.0089(12) -0.0139(12) C40 0.0322(14) 0.0495(17) 0.0291(13) 0.0065(11) 0.0075(11) -0.0044(12) C41 0.0324(13) 0.0332(13) 0.0311(13) -0.0056(10) -0.0003(11) -0.0007(11) C42 0.0218(11) 0.0287(12) 0.0270(12) -0.0004(9) -0.0026(9) -0.0079(9) C43 0.0251(11) 0.0274(11) 0.0248(11) -0.0061(9) 0.0011(9) -0.0097(9) C44 0.0383(14) 0.0337(13) 0.0267(12) -0.0087(10) 0.0011(10) -0.0153(11) C45 0.0464(16) 0.0276(13) 0.0430(16) -0.0117(11) 0.0128(13) -0.0125(12) C46 0.0366(15) 0.0319(14) 0.0483(17) 0.0020(12) 0.0044(13) -0.0008(11) C47 0.0397(15) 0.0439(16) 0.0370(15) -0.0012(12) -0.0106(12) -0.0066(12) C48 0.0346(14) 0.0325(13) 0.0317(13) -0.0074(10) -0.0040(11) -0.0078(11) C49 0.0267(12) 0.0266(11) 0.0263(12) -0.0056(9) -0.0024(9) -0.0094(9) C50 0.0279(13) 0.0352(13) 0.0351(14) -0.0093(10) -0.0042(10) -0.0092(10) C51 0.0399(15) 0.0399(15) 0.0442(16) -0.0064(12) -0.0214(13) -0.0086(12) C52 0.065(2) 0.0396(15) 0.0258(13) -0.0068(11) -0.0152(13) -0.0070(14) C53 0.0498(17) 0.0342(14) 0.0237(12) -0.0046(10) 0.0028(11) -0.0055(12) C54 0.0292(12) 0.0283(12) 0.0280(12) -0.0037(9) -0.0024(10) -0.0064(10) C101 0.030(3) 0.065(4) 0.034(3) -0.038(4) -0.022(2) 0.031(3) C102 0.054(4) 0.069(5) 0.032(3) -0.011(3) -0.018(3) 0.010(3) C103 0.065(5) 0.170(12) 0.035(4) 0.020(5) -0.006(4) 0.007(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 C1 1.784(2) . ? P1 C7 1.790(2) . ? P1 C13 1.791(2) . ? P1 C19 1.809(2) . ? P2 F1 1.6539(15) . ? P2 F2 1.6581(16) . ? P2 C25 1.804(3) . ? P2 C31 1.807(2) . ? P2 C22 1.827(2) . ? F3 C21 1.339(3) . ? F4 C20 1.336(3) . ? F5 C24 1.344(3) . ? F6 C23 1.336(3) . ? F7 B1 1.429(3) . ? F8 C38 1.348(3) . ? F9 C39 1.342(3) . ? F10 C40 1.340(3) . ? F11 C41 1.343(3) . ? F12 C42 1.348(3) . ? F13 C44 1.350(3) . ? F14 C45 1.344(3) . ? F15 C46 1.350(3) . ? F16 C47 1.341(3) . ? F17 C48 1.350(3) . ? F18 C50 1.355(3) . ? F19 C51 1.347(3) . ? F20 C52 1.346(3) . ? F21 C53 1.347(3) . ? F22 C54 1.354(3) . ? B1 C49 1.642(3) . ? B1 C37 1.647(3) . ? B1 C43 1.655(4) . ? C1 C6 1.390(3) . ? C1 C2 1.392(3) . ? C2 C3 1.385(4) . ? C3 C4 1.386(4) . ? C4 C5 1.370(4) . ? C5 C6 1.387(4) . ? C7 C12 1.386(3) . ? C7 C8 1.394(3) . ? C8 C9 1.383(4) . ? C9 C10 1.383(4) . ? C10 C11 1.378(4) . ? C11 C12 1.388(3) . ? C13 C18 1.387(3) . ? C13 C14 1.391(3) . ? C14 C15 1.384(4) . ? C15 C16 1.384(4) . ? C16 C17 1.376(4) . ? C17 C18 1.384(3) . ? C19 C20 1.388(3) . ? C19 C24 1.389(3) . ? C20 C21 1.384(3) . ? C21 C22 1.382(3) . ? C22 C23 1.386(3) . ? C23 C24 1.379(3) . ? C25 C30 1.391(4) . ? C25 C26 1.401(4) . ? C26 C27 1.381(5) . ? C27 C28 1.374(6) . ? C28 C29 1.357(6) . ? C29 C30 1.403(5) . ? C31 C32 1.391(3) . ? C31 C36 1.391(4) . ? C32 C33 1.399(4) . ? C33 C34 1.369(5) . ? C34 C35 1.378(5) . ? C35 C36 1.382(4) . ? C37 C42 1.381(3) . ? C37 C38 1.389(3) . ? C38 C39 1.383(4) . ? C39 C40 1.369(4) . ? C40 C41 1.369(4) . ? C41 C42 1.387(4) . ? C43 C48 1.383(3) . ? C43 C44 1.391(3) . ? C44 C45 1.381(4) . ? C45 C46 1.371(4) . ? C46 C47 1.370(4) . ? C47 C48 1.379(4) . ? C49 C50 1.381(3) . ? C49 C54 1.386(3) . ? C50 C51 1.380(4) . ? C51 C52 1.362(5) . ? C52 C53 1.373(4) . ? C53 C54 1.377(4) . ? C101 C101 1.151(14) 2_565 ? C101 C102 1.460(7) . ? C102 C103 1.420(8) . ? 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 C1 P1 C7 108.70(10) . . ? C1 P1 C13 108.33(11) . . ? C7 P1 C13 111.41(10) . . ? C1 P1 C19 112.97(10) . . ? C7 P1 C19 106.22(10) . . ? C13 P1 C19 109.25(10) . . ? F1 P2 F2 175.17(8) . . ? F1 P2 C25 92.56(11) . . ? F2 P2 C25 91.48(11) . . ? F1 P2 C31 89.95(10) . . ? F2 P2 C31 90.18(10) . . ? C25 P2 C31 121.92(11) . . ? F1 P2 C22 87.81(9) . . ? F2 P2 C22 87.88(9) . . ? C25 P2 C22 119.65(11) . . ? C31 P2 C22 118.42(11) . . ? F7 B1 C49 106.59(19) . . ? F7 B1 C37 109.11(18) . . ? C49 B1 C37 113.70(19) . . ? F7 B1 C43 106.52(19) . . ? C49 B1 C43 111.25(19) . . ? C37 B1 C43 109.37(19) . . ? C6 C1 C2 120.8(2) . . ? C6 C1 P1 120.78(18) . . ? C2 C1 P1 118.36(17) . . ? C3 C2 C1 118.9(2) . . ? C2 C3 C4 120.5(3) . . ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.8(3) . . ? C5 C6 C1 119.0(2) . . ? C12 C7 C8 120.3(2) . . ? C12 C7 P1 121.25(18) . . ? C8 C7 P1 118.26(17) . . ? C9 C8 C7 119.6(2) . . ? C10 C9 C8 119.9(2) . . ? C11 C10 C9 120.6(2) . . ? C10 C11 C12 120.0(2) . . ? C7 C12 C11 119.5(2) . . ? C18 C13 C14 119.9(2) . . ? C18 C13 P1 122.81(18) . . ? C14 C13 P1 117.29(18) . . ? C15 C14 C13 119.8(2) . . ? C14 C15 C16 120.0(3) . . ? C17 C16 C15 120.0(2) . . ? C16 C17 C18 120.6(2) . . ? C17 C18 C13 119.6(2) . . ? C20 C19 C24 116.4(2) . . ? C20 C19 P1 125.46(17) . . ? C24 C19 P1 118.17(16) . . ? F4 C20 C21 117.5(2) . . ? F4 C20 C19 121.2(2) . . ? C21 C20 C19 121.3(2) . . ? F3 C21 C22 120.2(2) . . ? F3 C21 C20 117.7(2) . . ? C22 C21 C20 122.1(2) . . ? C21 C22 C23 116.6(2) . . ? C21 C22 P2 121.83(17) . . ? C23 C22 P2 121.50(17) . . ? F6 C23 C24 118.0(2) . . ? F6 C23 C22 120.6(2) . . ? C24 C23 C22 121.4(2) . . ? F5 C24 C23 118.3(2) . . ? F5 C24 C19 119.5(2) . . ? C23 C24 C19 122.1(2) . . ? C30 C25 C26 119.2(3) . . ? C30 C25 P2 120.2(2) . . ? C26 C25 P2 120.7(2) . . ? C27 C26 C25 119.8(3) . . ? C28 C27 C26 120.5(4) . . ? C29 C28 C27 120.5(3) . . ? C28 C29 C30 120.5(4) . . ? C25 C30 C29 119.4(3) . . ? C32 C31 C36 119.7(2) . . ? C32 C31 P2 120.29(19) . . ? C36 C31 P2 120.05(19) . . ? C31 C32 C33 119.5(3) . . ? C34 C33 C32 120.2(3) . . ? C33 C34 C35 120.3(3) . . ? C34 C35 C36 120.4(3) . . ? C35 C36 C31 119.8(3) . . ? C42 C37 C38 113.4(2) . . ? C42 C37 B1 124.1(2) . . ? C38 C37 B1 122.5(2) . . ? F8 C38 C39 116.6(2) . . ? F8 C38 C37 119.0(2) . . ? C39 C38 C37 124.4(3) . . ? F9 C39 C40 119.8(3) . . ? F9 C39 C38 120.8(3) . . ? C40 C39 C38 119.4(3) . . ? F10 C40 C39 120.9(3) . . ? F10 C40 C41 120.0(3) . . ? C39 C40 C41 119.1(2) . . ? F11 C41 C40 119.4(2) . . ? F11 C41 C42 121.0(3) . . ? C40 C41 C42 119.6(2) . . ? F12 C42 C37 121.3(2) . . ? F12 C42 C41 114.6(2) . . ? C37 C42 C41 124.1(2) . . ? C48 C43 C44 113.5(2) . . ? C48 C43 B1 118.9(2) . . ? C44 C43 B1 127.6(2) . . ? F13 C44 C45 115.4(2) . . ? F13 C44 C43 120.7(2) . . ? C45 C44 C43 123.9(2) . . ? F14 C45 C46 119.8(3) . . ? F14 C45 C44 120.7(3) . . ? C46 C45 C44 119.5(2) . . ? F15 C46 C47 120.3(3) . . ? F15 C46 C45 120.4(3) . . ? C47 C46 C45 119.3(3) . . ? F16 C47 C46 120.1(3) . . ? F16 C47 C48 120.6(3) . . ? C46 C47 C48 119.3(3) . . ? F17 C48 C47 116.2(2) . . ? F17 C48 C43 119.4(2) . . ? C47 C48 C43 124.5(2) . . ? C50 C49 C54 113.3(2) . . ? C50 C49 B1 127.9(2) . . ? C54 C49 B1 118.8(2) . . ? F18 C50 C51 114.9(2) . . ? F18 C50 C49 121.1(2) . . ? C51 C50 C49 123.9(3) . . ? F19 C51 C52 119.6(3) . . ? F19 C51 C50 120.6(3) . . ? C52 C51 C50 119.8(3) . . ? F20 C52 C51 119.8(3) . . ? F20 C52 C53 120.9(3) . . ? C51 C52 C53 119.3(2) . . ? F21 C53 C52 120.3(2) . . ? F21 C53 C54 120.8(3) . . ? C52 C53 C54 118.9(3) . . ? F22 C54 C53 115.8(2) . . ? F22 C54 C49 119.5(2) . . ? C53 C54 C49 124.7(2) . . ? C101 C101 C102 110.0(7) 2_565 . ? C103 C102 C101 105.3(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.305 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.079 data_ljh010_0m _database_code_depnum_ccdc_archive 'CCDC 904901' #TrackingRef 'All-CIFs-4-structures-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H20 F12 O6 P2 S2' _chemical_formula_weight 854.54 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5862(6) _cell_length_b 14.4109(6) _cell_length_c 17.6835(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.851(2) _cell_angle_gamma 90.00 _cell_volume 3473.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5150 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 23.64 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.354 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6418 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32487 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28.06 _reflns_number_total 8380 _reflns_number_gt 4555 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1185P)^2^+3.5477P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8380 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.2478 _refine_ls_wR_factor_gt 0.2059 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 -0.19169(7) 0.41972(7) 0.36112(6) 0.0353(3) Uani 1 1 d . . . P2 P 0.18257(7) 0.57734(7) 0.14892(6) 0.0360(3) Uani 1 1 d . . . S1 S 0.97000(8) 0.23404(7) 0.10538(6) 0.0409(3) Uani 1 1 d . . . S2 S 0.02699(11) 0.75959(12) 0.40487(8) 0.0698(4) Uani 1 1 d . . . O1 O 0.9864(3) 0.3182(2) 0.0709(2) 0.0774(11) Uani 1 1 d . . . O2 O 1.0555(3) 0.1898(3) 0.1584(2) 0.0758(11) Uani 1 1 d . . . O3 O 0.8995(3) 0.1753(2) 0.0502(2) 0.0662(10) Uani 1 1 d . . . O4 O 0.0738(6) 0.8302(8) 0.4515(5) 0.270(6) Uani 1 1 d . . . O5 O -0.0728(3) 0.7580(4) 0.3687(3) 0.127(2) Uani 1 1 d . . . O6 O 0.0601(5) 0.6812(8) 0.4427(7) 0.334(9) Uani 1 1 d . . . F1 F -0.17907(18) 0.5667(2) 0.48324(19) 0.0742(10) Uani 1 1 d . . . F2 F 0.18332(17) 0.4544(2) 0.00953(18) 0.0715(9) Uani 1 1 d . . . F3 F -0.03202(19) 0.6006(2) 0.11652(16) 0.0684(9) Uani 1 1 d . . . F4 F 0.02282(19) 0.3729(2) 0.39629(18) 0.0769(10) Uani 1 1 d . . . F5 F -0.16184(17) 0.32104(16) 0.34607(14) 0.0481(6) Uani 1 1 d . . . F6 F 0.14638(18) 0.67299(16) 0.16487(15) 0.0499(6) Uani 1 1 d . . . F7 F 0.8256(3) 0.3132(4) 0.1341(3) 0.147(2) Uani 1 1 d . . . F8 F 0.8854(4) 0.2007(3) 0.2105(3) 0.1330(17) Uani 1 1 d . . . F9 F 0.9609(3) 0.3277(3) 0.2288(2) 0.1168(15) Uani 1 1 d . . . F10 F 0.0448(6) 0.6872(7) 0.2830(6) 0.279(6) Uani 1 1 d . . . F11 F 0.0504(7) 0.8240(7) 0.2804(4) 0.276(5) Uani 1 1 d . . . F12 F 0.1713(4) 0.7623(5) 0.3538(4) 0.169(2) Uani 1 1 d . . . C1 C -0.2204(3) 0.4843(3) 0.2716(2) 0.0393(9) Uani 1 1 d . . . C2 C -0.1750(4) 0.5685(3) 0.2700(3) 0.0535(12) Uani 1 1 d . . . H2A H -0.1254 0.5911 0.3165 0.064 Uiso 1 1 calc R . . C3 C -0.2043(4) 0.6183(4) 0.1986(3) 0.0667(14) Uani 1 1 d . . . H3A H -0.1760 0.6765 0.1969 0.080 Uiso 1 1 calc R . . C4 C -0.2745(4) 0.5834(4) 0.1302(3) 0.0684(16) Uani 1 1 d . . . H4A H -0.2928 0.6174 0.0817 0.082 Uiso 1 1 calc R . . C5 C -0.3181(4) 0.4998(4) 0.1316(3) 0.0608(14) Uani 1 1 d . . . H5A H -0.3658 0.4769 0.0841 0.073 Uiso 1 1 calc R . . C6 C -0.2930(3) 0.4489(3) 0.2021(3) 0.0492(11) Uani 1 1 d . . . H6A H -0.3238 0.3919 0.2035 0.059 Uiso 1 1 calc R . . C7 C -0.2930(3) 0.4049(3) 0.3924(2) 0.0379(9) Uani 1 1 d . . . C8 C -0.3702(3) 0.4676(3) 0.3665(3) 0.0460(10) Uani 1 1 d . . . H8A H -0.3681 0.5184 0.3338 0.055 Uiso 1 1 calc R . . C9 C -0.4507(3) 0.4536(4) 0.3897(3) 0.0530(12) Uani 1 1 d . . . H9A H -0.5030 0.4962 0.3739 0.064 Uiso 1 1 calc R . . C10 C -0.4541(3) 0.3785(4) 0.4354(3) 0.0554(12) Uani 1 1 d . . . H10A H -0.5101 0.3682 0.4487 0.067 Uiso 1 1 calc R . . C11 C -0.3773(4) 0.3180(3) 0.4620(3) 0.0614(13) Uani 1 1 d . . . H11A H -0.3802 0.2675 0.4947 0.074 Uiso 1 1 calc R . . C12 C -0.2961(4) 0.3304(3) 0.4415(3) 0.0515(11) Uani 1 1 d . . . H12A H -0.2429 0.2890 0.4603 0.062 Uiso 1 1 calc R . . C13 C -0.0833(3) 0.4654(3) 0.4376(2) 0.0336(8) Uani 1 1 d . . . C14 C -0.0901(3) 0.5316(3) 0.4923(3) 0.0427(10) Uani 1 1 d . . . C15 C 0.0936(3) 0.4784(3) 0.0052(3) 0.0418(10) Uani 1 1 d . . . C16 C 0.0807(3) 0.5321(3) 0.0662(2) 0.0338(8) Uani 1 1 d . . . C17 C -0.0148(3) 0.5512(3) 0.0598(2) 0.0397(9) Uani 1 1 d . . . C18 C 0.0097(3) 0.4359(3) 0.4465(2) 0.0416(10) Uani 1 1 d . . . C19 C 0.2855(3) 0.5994(3) 0.1222(2) 0.0382(9) Uani 1 1 d . . . C20 C 0.2764(3) 0.6598(3) 0.0588(3) 0.0481(11) Uani 1 1 d . . . H20A H 0.2158 0.6878 0.0301 0.058 Uiso 1 1 calc R . . C21 C 0.3570(4) 0.6779(3) 0.0385(3) 0.0541(12) Uani 1 1 d . . . H21A H 0.3517 0.7188 -0.0043 0.065 Uiso 1 1 calc R . . C22 C 0.4450(4) 0.6370(4) 0.0801(3) 0.0635(14) Uani 1 1 d . . . H22A H 0.5002 0.6505 0.0663 0.076 Uiso 1 1 calc R . . C23 C 0.4532(4) 0.5761(4) 0.1421(3) 0.0752(17) Uani 1 1 d . . . H23A H 0.5139 0.5474 0.1696 0.090 Uiso 1 1 calc R . . C24 C 0.3737(3) 0.5564(4) 0.1644(3) 0.0617(14) Uani 1 1 d . . . H24A H 0.3794 0.5151 0.2069 0.074 Uiso 1 1 calc R . . C25 C 0.2067(3) 0.5081(3) 0.2353(2) 0.0396(9) Uani 1 1 d . . . C26 C 0.1717(4) 0.4182(3) 0.2282(3) 0.0513(11) Uani 1 1 d . . . H26A H 0.1305 0.3954 0.1778 0.062 Uiso 1 1 calc R . . C27 C 0.1978(4) 0.3620(3) 0.2961(3) 0.0594(13) Uani 1 1 d . . . H27A H 0.1769 0.2999 0.2915 0.071 Uiso 1 1 calc R . . C28 C 0.2543(4) 0.3972(4) 0.3701(3) 0.0571(13) Uani 1 1 d . . . H28A H 0.2695 0.3596 0.4164 0.069 Uiso 1 1 calc R . . C29 C 0.2887(4) 0.4860(4) 0.3775(3) 0.0611(14) Uani 1 1 d . . . H29A H 0.3278 0.5087 0.4286 0.073 Uiso 1 1 calc R . . C30 C 0.2666(3) 0.5432(3) 0.3102(3) 0.0524(11) Uani 1 1 d . . . H30A H 0.2912 0.6040 0.3150 0.063 Uiso 1 1 calc R . . C31 C 0.9080(4) 0.2721(4) 0.1735(3) 0.0645(14) Uani 1 1 d . . . C32 C 0.0793(7) 0.7597(7) 0.3304(5) 0.112(3) 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 0.0337(5) 0.0361(6) 0.0346(5) -0.0036(4) 0.0102(4) 0.0011(4) P2 0.0318(5) 0.0392(6) 0.0346(5) -0.0015(4) 0.0087(4) -0.0007(4) S1 0.0454(6) 0.0410(6) 0.0356(5) 0.0005(4) 0.0137(5) 0.0076(5) S2 0.0558(8) 0.1048(12) 0.0470(7) 0.0078(7) 0.0162(7) -0.0082(8) O1 0.109(3) 0.061(2) 0.070(2) 0.0105(19) 0.040(2) -0.008(2) O2 0.065(2) 0.093(3) 0.061(2) 0.003(2) 0.0125(19) 0.036(2) O3 0.073(2) 0.066(2) 0.058(2) -0.0229(17) 0.0220(19) -0.0126(19) O4 0.225(8) 0.428(14) 0.218(8) -0.256(10) 0.154(7) -0.190(9) O5 0.059(3) 0.184(5) 0.128(4) -0.069(4) 0.020(3) 0.014(3) O6 0.126(6) 0.436(15) 0.440(15) 0.390(14) 0.099(8) 0.072(8) F1 0.0337(14) 0.091(2) 0.090(2) -0.0487(17) 0.0125(15) 0.0087(14) F2 0.0280(13) 0.099(2) 0.083(2) -0.0429(17) 0.0145(14) 0.0045(14) F3 0.0439(16) 0.104(2) 0.0616(17) -0.0447(16) 0.0239(14) -0.0070(14) F4 0.0448(16) 0.105(2) 0.080(2) -0.0584(18) 0.0199(15) 0.0024(15) F5 0.0488(14) 0.0397(13) 0.0560(15) -0.0120(11) 0.0189(12) 0.0016(11) F6 0.0472(14) 0.0443(14) 0.0595(15) -0.0100(11) 0.0206(12) -0.0005(11) F7 0.102(3) 0.240(6) 0.096(3) -0.032(3) 0.031(3) 0.093(4) F8 0.170(5) 0.149(4) 0.126(4) 0.004(3) 0.109(4) -0.016(3) F9 0.109(3) 0.160(4) 0.087(3) -0.073(3) 0.042(2) -0.014(3) F10 0.241(8) 0.368(12) 0.324(10) -0.245(10) 0.217(8) -0.150(8) F11 0.282(10) 0.388(13) 0.144(6) 0.161(8) 0.057(6) -0.007(9) F12 0.108(4) 0.267(7) 0.172(5) -0.007(5) 0.098(4) -0.023(4) C1 0.034(2) 0.050(2) 0.035(2) -0.0004(17) 0.0126(18) 0.0023(18) C2 0.052(3) 0.055(3) 0.048(3) 0.008(2) 0.012(2) -0.005(2) C3 0.065(3) 0.070(4) 0.066(3) 0.025(3) 0.024(3) 0.002(3) C4 0.066(4) 0.103(5) 0.041(3) 0.026(3) 0.025(3) 0.033(3) C5 0.049(3) 0.087(4) 0.038(2) -0.011(3) 0.006(2) 0.021(3) C6 0.044(3) 0.062(3) 0.037(2) -0.005(2) 0.007(2) 0.007(2) C7 0.033(2) 0.041(2) 0.036(2) -0.0015(17) 0.0091(18) -0.0047(17) C8 0.039(2) 0.046(3) 0.053(3) 0.009(2) 0.016(2) 0.0009(19) C9 0.039(2) 0.065(3) 0.055(3) 0.004(2) 0.016(2) 0.007(2) C10 0.043(3) 0.072(3) 0.051(3) -0.002(2) 0.017(2) -0.015(2) C11 0.082(4) 0.052(3) 0.061(3) 0.008(2) 0.038(3) -0.013(3) C12 0.058(3) 0.044(3) 0.053(3) 0.005(2) 0.021(2) 0.005(2) C13 0.034(2) 0.038(2) 0.0277(18) 0.0000(15) 0.0089(16) 0.0008(16) C14 0.031(2) 0.049(2) 0.050(2) -0.008(2) 0.0157(19) 0.0083(18) C15 0.030(2) 0.051(3) 0.047(2) -0.0052(19) 0.0166(19) 0.0037(18) C16 0.033(2) 0.035(2) 0.0316(19) 0.0046(16) 0.0098(17) 0.0008(16) C17 0.039(2) 0.048(2) 0.036(2) -0.0057(17) 0.0178(19) 0.0001(18) C18 0.040(2) 0.048(2) 0.041(2) -0.0142(18) 0.019(2) 0.0014(18) C19 0.032(2) 0.043(2) 0.035(2) 0.0005(17) 0.0058(18) -0.0041(17) C20 0.049(3) 0.045(3) 0.049(3) 0.010(2) 0.016(2) 0.003(2) C21 0.062(3) 0.055(3) 0.050(3) 0.003(2) 0.026(2) -0.010(2) C22 0.044(3) 0.095(4) 0.056(3) -0.004(3) 0.024(3) -0.011(3) C23 0.037(3) 0.116(5) 0.074(4) 0.022(3) 0.020(3) 0.015(3) C24 0.041(3) 0.093(4) 0.050(3) 0.026(3) 0.015(2) 0.015(2) C25 0.035(2) 0.049(2) 0.032(2) 0.0010(17) 0.0082(18) -0.0047(18) C26 0.054(3) 0.050(3) 0.038(2) 0.001(2) 0.001(2) -0.006(2) C27 0.067(3) 0.054(3) 0.047(3) 0.010(2) 0.008(2) -0.007(2) C28 0.057(3) 0.072(4) 0.039(2) 0.013(2) 0.013(2) 0.007(3) C29 0.055(3) 0.089(4) 0.027(2) -0.007(2) -0.001(2) -0.007(3) C30 0.050(3) 0.062(3) 0.039(2) -0.009(2) 0.009(2) -0.016(2) C31 0.066(4) 0.081(4) 0.049(3) -0.012(3) 0.023(3) 0.019(3) C32 0.106(7) 0.147(8) 0.089(6) -0.016(5) 0.043(5) -0.010(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 F5 1.538(2) . ? P1 C1 1.754(4) . ? P1 C7 1.765(4) . ? P1 C13 1.800(4) . ? P2 F6 1.538(3) . ? P2 C25 1.752(4) . ? P2 C19 1.756(4) . ? P2 C16 1.796(4) . ? S1 O1 1.416(4) . ? S1 O2 1.417(3) . ? S1 O3 1.418(3) . ? S1 C31 1.830(5) . ? S2 O6 1.314(7) . ? S2 O4 1.334(6) . ? S2 O5 1.366(5) . ? S2 C32 1.741(8) . ? F1 C14 1.348(4) . ? F2 C15 1.329(4) . ? F3 C17 1.324(4) . ? F4 C18 1.331(4) . ? F7 C31 1.298(6) . ? F8 C31 1.322(7) . ? F9 C31 1.287(6) . ? F10 C32 1.323(10) . ? F11 C32 1.246(11) . ? F12 C32 1.256(9) . ? C1 C2 1.387(6) . ? C1 C6 1.402(6) . ? C2 C3 1.382(6) . ? C3 C4 1.373(8) . ? C4 C5 1.367(8) . ? C5 C6 1.379(7) . ? C7 C8 1.388(6) . ? C7 C12 1.391(6) . ? C8 C9 1.390(6) . ? C9 C10 1.361(7) . ? C10 C11 1.364(7) . ? C11 C12 1.369(7) . ? C13 C18 1.377(5) . ? C13 C14 1.386(5) . ? C14 C18 1.364(6) 3_566 ? C15 C17 1.372(6) 3_565 ? C15 C16 1.393(5) . ? C16 C17 1.385(5) . ? C17 C15 1.372(6) 3_565 ? C18 C14 1.364(6) 3_566 ? C19 C24 1.382(6) . ? C19 C20 1.389(6) . ? C20 C21 1.371(6) . ? C21 C22 1.365(7) . ? C22 C23 1.376(7) . ? C23 C24 1.381(7) . ? C25 C26 1.383(6) . ? C25 C30 1.397(5) . ? C26 C27 1.385(6) . ? C27 C28 1.371(7) . ? C28 C29 1.364(7) . ? C29 C30 1.386(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 F5 P1 C1 109.02(17) . . ? F5 P1 C7 105.20(17) . . ? C1 P1 C7 112.91(19) . . ? F5 P1 C13 103.99(16) . . ? C1 P1 C13 110.37(19) . . ? C7 P1 C13 114.69(18) . . ? F6 P2 C25 109.04(17) . . ? F6 P2 C19 105.64(17) . . ? C25 P2 C19 114.29(19) . . ? F6 P2 C16 103.67(16) . . ? C25 P2 C16 110.79(18) . . ? C19 P2 C16 112.65(18) . . ? O1 S1 O2 115.3(3) . . ? O1 S1 O3 114.1(2) . . ? O2 S1 O3 116.0(2) . . ? O1 S1 C31 103.0(3) . . ? O2 S1 C31 103.0(2) . . ? O3 S1 C31 103.0(2) . . ? O6 S2 O4 109.1(7) . . ? O6 S2 O5 111.2(5) . . ? O4 S2 O5 121.9(5) . . ? O6 S2 C32 101.8(6) . . ? O4 S2 C32 101.6(5) . . ? O5 S2 C32 109.0(4) . . ? C2 C1 C6 121.2(4) . . ? C2 C1 P1 121.3(3) . . ? C6 C1 P1 117.5(3) . . ? C3 C2 C1 118.6(5) . . ? C4 C3 C2 120.4(5) . . ? C5 C4 C3 120.8(5) . . ? C4 C5 C6 120.7(5) . . ? C5 C6 C1 118.2(5) . . ? C8 C7 C12 120.3(4) . . ? C8 C7 P1 119.3(3) . . ? C12 C7 P1 120.4(3) . . ? C7 C8 C9 118.7(4) . . ? C10 C9 C8 120.2(4) . . ? C9 C10 C11 121.0(4) . . ? C10 C11 C12 120.4(4) . . ? C11 C12 C7 119.3(4) . . ? C18 C13 C14 116.4(3) . . ? C18 C13 P1 122.6(3) . . ? C14 C13 P1 121.0(3) . . ? F1 C14 C18 119.0(4) . 3_566 ? F1 C14 C13 118.6(4) . . ? C18 C14 C13 122.3(3) 3_566 . ? F2 C15 C17 118.8(4) . 3_565 ? F2 C15 C16 120.0(4) . . ? C17 C15 C16 121.2(3) 3_565 . ? C17 C16 C15 117.2(3) . . ? C17 C16 P2 120.7(3) . . ? C15 C16 P2 122.1(3) . . ? F3 C17 C15 118.3(4) . 3_565 ? F3 C17 C16 120.1(4) . . ? C15 C17 C16 121.6(4) 3_565 . ? F4 C18 C14 118.4(4) . 3_566 ? F4 C18 C13 120.3(4) . . ? C14 C18 C13 121.2(4) 3_566 . ? C24 C19 C20 121.3(4) . . ? C24 C19 P2 119.7(3) . . ? C20 C19 P2 119.0(3) . . ? C21 C20 C19 119.1(4) . . ? C22 C21 C20 120.4(4) . . ? C21 C22 C23 120.2(4) . . ? C22 C23 C24 121.0(5) . . ? C23 C24 C19 118.0(4) . . ? C26 C25 C30 120.7(4) . . ? C26 C25 P2 120.1(3) . . ? C30 C25 P2 119.0(3) . . ? C25 C26 C27 119.4(4) . . ? C28 C27 C26 119.8(5) . . ? C29 C28 C27 120.9(4) . . ? C28 C29 C30 120.7(4) . . ? C29 C30 C25 118.4(4) . . ? F9 C31 F7 108.4(5) . . ? F9 C31 F8 107.3(5) . . ? F7 C31 F8 105.9(6) . . ? F9 C31 S1 112.5(4) . . ? F7 C31 S1 111.3(4) . . ? F8 C31 S1 111.2(4) . . ? F11 C32 F12 105.3(9) . . ? F11 C32 F10 100.4(9) . . ? F12 C32 F10 110.6(9) . . ? F11 C32 S2 114.2(8) . . ? F12 C32 S2 117.1(7) . . ? F10 C32 S2 108.0(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.900 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.082 data_ljh030_0m _database_code_depnum_ccdc_archive 'CCDC 904902' #TrackingRef 'All-CIFs-4-structures-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 F6 P2' _chemical_formula_weight 556.40 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.4223(17) _cell_length_b 8.9674(10) _cell_length_c 18.0179(17) _cell_angle_alpha 90.00 _cell_angle_beta 104.440(5) _cell_angle_gamma 90.00 _cell_volume 2569.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5901 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.31 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6839 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21903 _diffrn_reflns_av_R_equivalents 0.0699 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.35 _reflns_number_total 5797 _reflns_number_gt 3673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5797 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.0957 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 0.05684(4) 0.72051(7) 0.22917(3) 0.02125(16) Uani 1 1 d . . . P2 P 0.39511(4) 0.31245(7) 0.36500(3) 0.02230(16) Uani 1 1 d . . . F1 F 0.42092(8) 0.43638(15) 0.43573(7) 0.0286(3) Uani 1 1 d . . . F2 F 0.35966(8) 0.20083(14) 0.29055(7) 0.0261(3) Uani 1 1 d . . . F3 F 0.11917(9) 0.57406(15) 0.38358(7) 0.0325(4) Uani 1 1 d . . . F4 F 0.25555(8) 0.41572(16) 0.44148(7) 0.0311(3) Uani 1 1 d . . . F5 F 0.33559(8) 0.45770(16) 0.20549(7) 0.0303(3) Uani 1 1 d . . . F6 F 0.20061(8) 0.62020(16) 0.14841(7) 0.0296(3) Uani 1 1 d . . . C1 C -0.00149(14) 0.6129(3) 0.14605(12) 0.0211(5) Uani 1 1 d . . . C2 C 0.01594(15) 0.4653(3) 0.13084(13) 0.0246(5) Uani 1 1 d . . . H2A H 0.0660 0.4195 0.1598 0.029 Uiso 1 1 calc R . . C3 C -0.03892(16) 0.3844(3) 0.07388(13) 0.0295(6) Uani 1 1 d . . . H3A H -0.0260 0.2842 0.0640 0.035 Uiso 1 1 calc R . . C4 C -0.11234(16) 0.4495(3) 0.03154(13) 0.0326(6) Uani 1 1 d . . . H4A H -0.1501 0.3936 -0.0070 0.039 Uiso 1 1 calc R . . C5 C -0.13090(16) 0.5971(3) 0.04549(14) 0.0328(6) Uani 1 1 d . . . H5A H -0.1810 0.6422 0.0161 0.039 Uiso 1 1 calc R . . C6 C -0.07622(15) 0.6777(3) 0.10220(13) 0.0279(6) Uani 1 1 d . . . H6A H -0.0893 0.7780 0.1117 0.033 Uiso 1 1 calc R . . C7 C 0.09804(14) 0.8818(3) 0.18622(13) 0.0218(5) Uani 1 1 d . . . C8 C 0.09299(16) 0.9020(3) 0.10806(13) 0.0292(6) Uani 1 1 d . . . H8A H 0.0694 0.8257 0.0726 0.035 Uiso 1 1 calc R . . C9 C 0.12217(16) 1.0326(3) 0.08180(15) 0.0346(6) Uani 1 1 d . . . H9A H 0.1183 1.0450 0.0287 0.042 Uiso 1 1 calc R . . C10 C 0.15691(16) 1.1450(3) 0.13316(15) 0.0335(6) Uani 1 1 d . . . H10A H 0.1770 1.2340 0.1153 0.040 Uiso 1 1 calc R . . C11 C 0.16211(15) 1.1265(3) 0.21071(15) 0.0317(6) Uani 1 1 d . . . H11A H 0.1860 1.2031 0.2458 0.038 Uiso 1 1 calc R . . C12 C 0.13259(14) 0.9971(3) 0.23732(13) 0.0245(5) Uani 1 1 d . . . H12A H 0.1358 0.9863 0.2904 0.029 Uiso 1 1 calc R . . C13 C 0.15385(14) 0.6071(2) 0.26355(12) 0.0203(5) Uani 1 1 d . . . C14 C 0.17267(14) 0.5497(3) 0.33805(12) 0.0220(5) Uani 1 1 d . . . C15 C 0.24426(15) 0.4669(3) 0.36873(12) 0.0228(5) Uani 1 1 d . . . C16 C 0.30213(14) 0.4311(2) 0.32612(12) 0.0200(5) Uani 1 1 d . . . C17 C 0.28340(14) 0.4864(3) 0.25140(12) 0.0217(5) Uani 1 1 d . . . C18 C 0.21271(14) 0.5719(3) 0.22188(12) 0.0209(5) Uani 1 1 d . . . C19 C 0.49394(14) 0.3440(3) 0.33790(13) 0.0237(5) Uani 1 1 d . . . C20 C 0.55745(15) 0.4315(3) 0.38339(15) 0.0329(6) Uani 1 1 d . . . H20A H 0.5486 0.4783 0.4280 0.039 Uiso 1 1 calc R . . C21 C 0.63406(17) 0.4509(3) 0.36376(17) 0.0427(7) Uani 1 1 d . . . H21A H 0.6768 0.5103 0.3954 0.051 Uiso 1 1 calc R . . C22 C 0.64811(17) 0.3848(3) 0.29918(17) 0.0419(7) Uani 1 1 d . . . H22A H 0.7001 0.3991 0.2860 0.050 Uiso 1 1 calc R . . C23 C 0.58603(17) 0.2974(3) 0.25368(15) 0.0409(7) Uani 1 1 d . . . H23A H 0.5956 0.2516 0.2091 0.049 Uiso 1 1 calc R . . C24 C 0.50957(16) 0.2758(3) 0.27251(14) 0.0337(6) Uani 1 1 d . . . H24A H 0.4677 0.2145 0.2410 0.040 Uiso 1 1 calc R . . C25 C 0.38684(14) 0.1639(3) 0.43218(13) 0.0250(5) Uani 1 1 d . . . C26 C 0.33875(16) 0.0359(3) 0.40748(15) 0.0356(7) Uani 1 1 d . . . H26A H 0.3107 0.0251 0.3549 0.043 Uiso 1 1 calc R . . C27 C 0.33157(17) -0.0759(3) 0.45934(17) 0.0445(8) Uani 1 1 d . . . H27A H 0.2983 -0.1617 0.4420 0.053 Uiso 1 1 calc R . . C28 C 0.37259(18) -0.0621(3) 0.53564(17) 0.0458(8) Uani 1 1 d . . . H28A H 0.3669 -0.1376 0.5710 0.055 Uiso 1 1 calc R . . C29 C 0.42183(18) 0.0610(3) 0.56083(16) 0.0427(7) Uani 1 1 d . . . H29A H 0.4512 0.0687 0.6133 0.051 Uiso 1 1 calc R . . C30 C 0.42885(17) 0.1738(3) 0.51007(13) 0.0350(7) Uani 1 1 d . . . H30A H 0.4625 0.2587 0.5283 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0214(3) 0.0219(3) 0.0213(3) -0.0014(3) 0.0070(2) 0.0017(3) P2 0.0217(3) 0.0239(4) 0.0210(3) -0.0004(3) 0.0048(2) 0.0008(3) F1 0.0292(8) 0.0312(8) 0.0241(7) -0.0050(6) 0.0039(6) 0.0014(6) F2 0.0274(7) 0.0261(8) 0.0247(7) -0.0053(6) 0.0063(6) -0.0012(6) F3 0.0379(8) 0.0380(9) 0.0279(7) 0.0064(6) 0.0198(6) 0.0130(7) F4 0.0352(8) 0.0408(9) 0.0190(7) 0.0084(6) 0.0100(6) 0.0096(7) F5 0.0280(8) 0.0414(9) 0.0261(7) 0.0055(6) 0.0155(6) 0.0091(7) F6 0.0327(8) 0.0406(9) 0.0174(7) 0.0065(6) 0.0096(6) 0.0081(7) C1 0.0193(12) 0.0232(13) 0.0225(12) 0.0029(10) 0.0080(9) -0.0026(10) C2 0.0242(13) 0.0266(14) 0.0242(12) 0.0012(11) 0.0084(10) -0.0013(10) C3 0.0385(15) 0.0267(15) 0.0259(13) -0.0050(11) 0.0130(11) -0.0066(12) C4 0.0357(16) 0.0415(17) 0.0199(12) -0.0031(12) 0.0059(11) -0.0142(13) C5 0.0283(14) 0.0435(17) 0.0243(13) 0.0068(12) 0.0021(11) -0.0017(12) C6 0.0291(14) 0.0252(14) 0.0291(13) 0.0044(11) 0.0069(11) 0.0035(11) C7 0.0181(12) 0.0213(13) 0.0264(13) 0.0014(10) 0.0064(10) 0.0036(10) C8 0.0353(15) 0.0262(14) 0.0265(13) -0.0016(11) 0.0084(11) 0.0008(11) C9 0.0425(17) 0.0323(16) 0.0316(14) 0.0073(12) 0.0139(12) 0.0050(13) C10 0.0362(15) 0.0211(14) 0.0463(16) 0.0061(12) 0.0161(12) -0.0001(12) C11 0.0282(14) 0.0263(15) 0.0403(15) -0.0071(12) 0.0080(12) -0.0022(11) C12 0.0219(13) 0.0255(14) 0.0269(13) -0.0017(11) 0.0074(10) 0.0032(11) C13 0.0205(12) 0.0186(12) 0.0214(12) -0.0019(10) 0.0046(9) -0.0016(10) C14 0.0262(13) 0.0224(13) 0.0205(12) -0.0037(10) 0.0117(10) 0.0001(10) C15 0.0291(13) 0.0251(14) 0.0143(11) 0.0028(10) 0.0055(10) -0.0006(11) C16 0.0217(12) 0.0191(12) 0.0191(11) 0.0002(10) 0.0045(9) -0.0018(10) C17 0.0205(12) 0.0267(14) 0.0200(12) -0.0024(10) 0.0089(10) -0.0013(10) C18 0.0249(13) 0.0220(13) 0.0151(11) 0.0008(10) 0.0039(9) -0.0014(10) C19 0.0213(13) 0.0225(13) 0.0261(13) 0.0047(10) 0.0035(10) 0.0025(10) C20 0.0295(15) 0.0298(15) 0.0381(15) 0.0030(12) 0.0061(12) -0.0002(12) C21 0.0302(16) 0.0411(18) 0.0561(19) 0.0053(15) 0.0093(14) -0.0092(13) C22 0.0250(15) 0.0439(18) 0.0599(19) 0.0227(15) 0.0164(13) 0.0041(13) C23 0.0363(16) 0.0507(19) 0.0402(16) 0.0069(14) 0.0181(13) 0.0116(14) C24 0.0279(14) 0.0385(16) 0.0348(15) -0.0008(12) 0.0081(12) 0.0025(12) C25 0.0202(12) 0.0292(14) 0.0270(13) 0.0052(11) 0.0083(10) 0.0061(11) C26 0.0292(15) 0.0369(16) 0.0395(15) 0.0077(13) 0.0061(12) 0.0029(12) C27 0.0346(16) 0.0371(17) 0.064(2) 0.0158(15) 0.0156(14) -0.0007(13) C28 0.0481(19) 0.048(2) 0.0493(19) 0.0263(15) 0.0275(15) 0.0212(16) C29 0.0509(19) 0.050(2) 0.0296(14) 0.0136(14) 0.0148(13) 0.0180(16) C30 0.0413(16) 0.0378(17) 0.0262(14) 0.0018(12) 0.0087(12) 0.0082(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.838(2) . ? P1 C7 1.847(2) . ? P1 C13 1.861(2) . ? P2 F2 1.6585(13) . ? P2 F1 1.6641(14) . ? P2 C25 1.828(2) . ? P2 C19 1.830(2) . ? P2 C16 1.849(2) . ? F3 C14 1.361(3) . ? F4 C15 1.357(2) . ? F5 C17 1.356(3) . ? F6 C18 1.359(2) . ? C1 C2 1.396(3) . ? C1 C6 1.409(3) . ? C2 C3 1.389(3) . ? C3 C4 1.385(3) . ? C4 C5 1.395(4) . ? C5 C6 1.384(3) . ? C7 C8 1.402(3) . ? C7 C12 1.406(3) . ? C8 C9 1.393(3) . ? C9 C10 1.390(4) . ? C10 C11 1.388(4) . ? C11 C12 1.389(3) . ? C13 C14 1.398(3) . ? C13 C18 1.400(3) . ? C14 C15 1.384(3) . ? C15 C16 1.400(3) . ? C16 C17 1.395(3) . ? C17 C18 1.383(3) . ? C19 C20 1.396(3) . ? C19 C24 1.407(3) . ? C20 C21 1.400(4) . ? C21 C22 1.376(4) . ? C22 C23 1.381(4) . ? C23 C24 1.393(4) . ? C25 C26 1.401(3) . ? C25 C30 1.404(3) . ? C26 C27 1.395(4) . ? C27 C28 1.377(4) . ? C28 C29 1.376(4) . ? C29 C30 1.388(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 C1 P1 C7 103.93(10) . . ? C1 P1 C13 102.31(10) . . ? C7 P1 C13 101.24(10) . . ? F2 P2 F1 173.42(7) . . ? F2 P2 C25 91.53(9) . . ? F1 P2 C25 91.51(9) . . ? F2 P2 C19 91.91(9) . . ? F1 P2 C19 91.58(9) . . ? C25 P2 C19 120.45(10) . . ? F2 P2 C16 87.17(8) . . ? F1 P2 C16 86.25(8) . . ? C25 P2 C16 118.64(11) . . ? C19 P2 C16 120.90(10) . . ? C2 C1 C6 118.3(2) . . ? C2 C1 P1 124.56(17) . . ? C6 C1 P1 116.39(18) . . ? C3 C2 C1 120.9(2) . . ? C4 C3 C2 120.1(2) . . ? C3 C4 C5 120.0(2) . . ? C6 C5 C4 119.9(2) . . ? C5 C6 C1 120.8(2) . . ? C8 C7 C12 118.4(2) . . ? C8 C7 P1 125.87(18) . . ? C12 C7 P1 115.56(17) . . ? C9 C8 C7 120.7(2) . . ? C10 C9 C8 120.2(2) . . ? C11 C10 C9 119.7(2) . . ? C10 C11 C12 120.5(2) . . ? C11 C12 C7 120.5(2) . . ? C14 C13 C18 114.5(2) . . ? C14 C13 P1 119.13(17) . . ? C18 C13 P1 126.35(17) . . ? F3 C14 C15 117.21(19) . . ? F3 C14 C13 119.9(2) . . ? C15 C14 C13 122.9(2) . . ? F4 C15 C14 117.7(2) . . ? F4 C15 C16 120.3(2) . . ? C14 C15 C16 122.0(2) . . ? C17 C16 C15 115.6(2) . . ? C17 C16 P2 122.17(18) . . ? C15 C16 P2 122.24(16) . . ? F5 C17 C18 117.94(19) . . ? F5 C17 C16 120.0(2) . . ? C18 C17 C16 122.0(2) . . ? F6 C18 C17 117.1(2) . . ? F6 C18 C13 119.86(19) . . ? C17 C18 C13 123.0(2) . . ? C20 C19 C24 118.1(2) . . ? C20 C19 P2 120.86(19) . . ? C24 C19 P2 121.03(18) . . ? C19 C20 C21 120.6(3) . . ? C22 C21 C20 120.7(3) . . ? C21 C22 C23 119.4(3) . . ? C22 C23 C24 120.7(3) . . ? C23 C24 C19 120.5(2) . . ? C26 C25 C30 117.8(2) . . ? C26 C25 P2 121.04(18) . . ? C30 C25 P2 121.1(2) . . ? C27 C26 C25 120.7(2) . . ? C28 C27 C26 120.1(3) . . ? C29 C28 C27 120.1(3) . . ? C28 C29 C30 120.4(3) . . ? C29 C30 C25 120.8(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.405 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.069 #===end data_ljh031_0ma _database_code_depnum_ccdc_archive 'CCDC 910420' #TrackingRef 'All-CIFs-4-structures-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H10 F9 O3 P S' _chemical_formula_weight 520.30 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 17.5800(11) _cell_length_b 12.4210(7) _cell_length_c 18.6519(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4072.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9167 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 29.24 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6268 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34987 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 29.58 _reflns_number_total 5704 _reflns_number_gt 3355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0369P)^2^+2.1394P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5704 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.01189(14) 0.7290(2) 0.38376(14) 0.0387(6) Uani 1 1 d . . . H1 H -0.0295 0.6907 0.4043 0.046 Uiso 1 1 calc R . . C2 C 0.06627(14) 0.7752(2) 0.42801(14) 0.0392(6) Uani 1 1 d . . . H9 H 0.0619 0.7688 0.4786 0.047 Uiso 1 1 calc R . . C3 C 0.12629(13) 0.8303(2) 0.39866(12) 0.0358(6) Uani 1 1 d . . . H10 H 0.1636 0.8624 0.4287 0.043 Uiso 1 1 calc R . . C4 C 0.13202(12) 0.83882(18) 0.32395(12) 0.0285(5) Uani 1 1 d . . . C5 C 0.29636(12) 0.88466(17) 0.32877(11) 0.0265(5) Uani 1 1 d . . . C6 C 0.30911(14) 0.7859(2) 0.36182(13) 0.0371(6) Uani 1 1 d . . . H6 H 0.2697 0.7336 0.3645 0.045 Uiso 1 1 calc R . . C7 C 0.37980(15) 0.7651(2) 0.39057(14) 0.0448(7) Uani 1 1 d . . . H5 H 0.3895 0.6977 0.4129 0.054 Uiso 1 1 calc R . . C8 C 0.43613(14) 0.8411(3) 0.38708(14) 0.0482(7) Uani 1 1 d . . . H2 H 0.4846 0.8261 0.4073 0.058 Uiso 1 1 calc R . . C9 C 0.22057(14) 0.9023(2) 0.04405(12) 0.0387(6) Uani 1 1 d . . . C10 C 0.26820(13) 0.8381(2) 0.08368(13) 0.0357(6) Uani 1 1 d . . . C11 C 0.26398(12) 0.83962(18) 0.15717(13) 0.0291(5) Uani 1 1 d . . . C12 C 0.21199(12) 0.90469(17) 0.19283(11) 0.0250(4) Uani 1 1 d . . . C13 C 0.42319(14) 0.9391(2) 0.35444(15) 0.0472(7) Uani 1 1 d . . . H4 H 0.4626 0.9913 0.3526 0.057 Uiso 1 1 calc R . . C14 C 0.35340(13) 0.9616(2) 0.32454(13) 0.0356(6) Uani 1 1 d . . . H3 H 0.3444 1.0286 0.3014 0.043 Uiso 1 1 calc R . . C15 C 0.01731(14) 0.7379(2) 0.31036(14) 0.0381(6) Uani 1 1 d . . . H8 H -0.0207 0.7067 0.2808 0.046 Uiso 1 1 calc R . . C16 C 0.07754(12) 0.79201(18) 0.27944(13) 0.0312(5) Uani 1 1 d . . . H7 H 0.0818 0.7972 0.2288 0.037 Uiso 1 1 calc R . . C17 C 0.16348(12) 0.96658(17) 0.15043(13) 0.0294(5) Uani 1 1 d . . . C18 C 0.16748(14) 0.96620(18) 0.07750(13) 0.0353(6) Uani 1 1 d . . . C19 C 0.44309(15) 1.03642(19) 0.12697(15) 0.0417(6) Uani 1 1 d . . . O1 O 0.32465(10) 1.08945(13) 0.05386(9) 0.0439(4) Uani 1 1 d . . . O2 O 0.39967(9) 1.23108(12) 0.10836(9) 0.0337(4) Uani 1 1 d . . . O3 O 0.32132(9) 1.11571(13) 0.18306(9) 0.0395(4) Uani 1 1 d . . . F1 F 0.22554(9) 0.90234(13) -0.02755(8) 0.0579(4) Uani 1 1 d . . . F2 F 0.31979(8) 0.77608(13) 0.05070(8) 0.0526(4) Uani 1 1 d . . . F3 F 0.31190(7) 0.77675(10) 0.19367(7) 0.0379(3) Uani 1 1 d . . . F4 F 0.19376(7) 1.03359(10) 0.30295(7) 0.0355(3) Uani 1 1 d . . . F5 F 0.11083(8) 1.02893(11) 0.18214(8) 0.0402(3) Uani 1 1 d . . . F6 F 0.12005(9) 1.02653(12) 0.03835(8) 0.0539(4) Uani 1 1 d . . . F7 F 0.41947(10) 0.93560(12) 0.13452(12) 0.0716(6) Uani 1 1 d . . . F8 F 0.48465(9) 1.05953(13) 0.18436(9) 0.0583(4) Uani 1 1 d . . . F9 F 0.48911(9) 1.04135(14) 0.07075(10) 0.0649(5) Uani 1 1 d . . . S1 S 0.36280(3) 1.12814(5) 0.11694(3) 0.03020(14) Uani 1 1 d . . . P1 P 0.20824(3) 0.91284(5) 0.28798(3) 0.02614(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0350(13) 0.0386(14) 0.0425(15) -0.0011(12) 0.0095(12) -0.0011(11) C2 0.0405(14) 0.0490(15) 0.0280(13) 0.0005(12) 0.0063(11) 0.0003(12) C3 0.0360(13) 0.0428(14) 0.0287(13) -0.0046(11) -0.0024(10) 0.0010(11) C4 0.0265(11) 0.0307(12) 0.0282(12) -0.0055(10) 0.0025(9) 0.0023(9) C5 0.0273(11) 0.0296(12) 0.0227(11) -0.0013(9) -0.0002(9) 0.0030(9) C6 0.0372(13) 0.0326(13) 0.0416(15) 0.0017(11) 0.0026(11) 0.0058(11) C7 0.0457(15) 0.0487(16) 0.0401(15) 0.0098(13) 0.0049(12) 0.0197(13) C8 0.0278(13) 0.081(2) 0.0362(15) 0.0006(15) -0.0010(11) 0.0140(14) C9 0.0495(15) 0.0425(15) 0.0240(12) -0.0009(11) 0.0006(11) -0.0116(12) C10 0.0348(13) 0.0383(14) 0.0339(13) -0.0115(11) 0.0070(11) -0.0017(11) C11 0.0261(11) 0.0265(12) 0.0346(13) -0.0009(10) -0.0017(10) -0.0011(9) C12 0.0262(11) 0.0237(10) 0.0250(11) -0.0008(9) -0.0008(9) -0.0042(9) C13 0.0293(13) 0.0635(19) 0.0489(17) 0.0034(14) -0.0020(12) -0.0049(13) C14 0.0325(13) 0.0405(14) 0.0339(14) 0.0032(11) 0.0003(10) -0.0031(11) C15 0.0335(13) 0.0405(14) 0.0403(15) -0.0087(12) 0.0017(11) -0.0062(11) C16 0.0319(12) 0.0359(13) 0.0259(12) -0.0056(10) 0.0026(10) 0.0012(10) C17 0.0291(11) 0.0244(11) 0.0348(13) -0.0006(10) -0.0020(10) -0.0016(10) C18 0.0419(14) 0.0299(12) 0.0342(14) 0.0055(11) -0.0087(11) -0.0028(11) C19 0.0418(14) 0.0292(13) 0.0540(18) -0.0029(12) 0.0052(13) -0.0005(11) O1 0.0523(11) 0.0414(10) 0.0380(10) 0.0026(8) -0.0053(8) -0.0122(9) O2 0.0404(9) 0.0264(8) 0.0342(9) 0.0000(7) 0.0073(7) -0.0048(7) O3 0.0382(9) 0.0435(10) 0.0368(10) 0.0083(8) 0.0117(8) -0.0012(8) F1 0.0755(11) 0.0714(11) 0.0268(8) -0.0006(8) 0.0022(7) -0.0057(9) F2 0.0506(9) 0.0639(10) 0.0433(9) -0.0184(8) 0.0106(7) 0.0077(8) F3 0.0371(8) 0.0379(8) 0.0388(8) -0.0061(6) -0.0037(6) 0.0110(6) F4 0.0406(8) 0.0254(7) 0.0404(8) -0.0071(6) -0.0044(6) 0.0061(6) F5 0.0390(8) 0.0401(8) 0.0416(9) -0.0015(7) -0.0058(6) 0.0139(6) F6 0.0714(11) 0.0504(9) 0.0398(9) 0.0114(7) -0.0171(8) 0.0094(8) F7 0.0590(10) 0.0289(8) 0.1269(18) 0.0053(9) -0.0050(11) 0.0046(8) F8 0.0502(9) 0.0626(11) 0.0622(11) -0.0042(9) -0.0145(8) 0.0125(8) F9 0.0584(10) 0.0693(12) 0.0670(12) -0.0141(9) 0.0245(9) 0.0157(9) S1 0.0332(3) 0.0270(3) 0.0304(3) 0.0025(2) 0.0039(3) -0.0024(2) P1 0.0271(3) 0.0241(3) 0.0273(3) -0.0037(2) -0.0019(2) 0.0023(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 C1 C15 1.377(3) . ? C1 C2 1.388(3) . ? C1 H1 0.9500 . ? C2 C3 1.372(3) . ? C2 H9 0.9500 . ? C3 C4 1.401(3) . ? C3 H10 0.9500 . ? C4 C16 1.395(3) . ? C4 P1 1.758(2) . ? C5 C14 1.388(3) . ? C5 C6 1.391(3) . ? C5 P1 1.761(2) . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7 C8 1.370(4) . ? C7 H5 0.9500 . ? C8 C13 1.381(4) . ? C8 H2 0.9500 . ? C9 F1 1.338(3) . ? C9 C10 1.372(3) . ? C9 C18 1.375(3) . ? C10 F2 1.340(3) . ? C10 C11 1.373(3) . ? C11 F3 1.335(2) . ? C11 C12 1.390(3) . ? C12 C17 1.394(3) . ? C12 P1 1.779(2) . ? C13 C14 1.376(3) . ? C13 H4 0.9500 . ? C14 H3 0.9500 . ? C15 C16 1.380(3) . ? C15 H8 0.9500 . ? C16 H7 0.9500 . ? C17 F5 1.344(3) . ? C17 C18 1.362(3) . ? C18 F6 1.338(3) . ? C19 F9 1.326(3) . ? C19 F7 1.327(3) . ? C19 F8 1.327(3) . ? C19 S1 1.824(3) . ? O1 S1 1.4370(17) . ? O2 S1 1.4424(16) . ? O3 S1 1.4411(16) . ? F4 P1 1.5467(13) . ? 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 C15 C1 C2 120.7(2) . . ? C15 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H9 120.0 . . ? C1 C2 H9 120.0 . . ? C2 C3 C4 119.3(2) . . ? C2 C3 H10 120.3 . . ? C4 C3 H10 120.3 . . ? C16 C4 C3 120.8(2) . . ? C16 C4 P1 120.95(17) . . ? C3 C4 P1 118.27(17) . . ? C14 C5 C6 121.1(2) . . ? C14 C5 P1 118.30(17) . . ? C6 C5 P1 120.56(17) . . ? C7 C6 C5 118.9(2) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H5 119.9 . . ? C6 C7 H5 119.9 . . ? C7 C8 C13 120.7(2) . . ? C7 C8 H2 119.7 . . ? C13 C8 H2 119.7 . . ? F1 C9 C10 119.9(2) . . ? F1 C9 C18 119.8(2) . . ? C10 C9 C18 120.3(2) . . ? F2 C10 C9 120.0(2) . . ? F2 C10 C11 120.2(2) . . ? C9 C10 C11 119.8(2) . . ? F3 C11 C10 117.8(2) . . ? F3 C11 C12 120.7(2) . . ? C10 C11 C12 121.4(2) . . ? C11 C12 C17 116.8(2) . . ? C11 C12 P1 122.35(17) . . ? C17 C12 P1 120.79(17) . . ? C14 C13 C8 120.3(3) . . ? C14 C13 H4 119.8 . . ? C8 C13 H4 119.8 . . ? C13 C14 C5 118.8(2) . . ? C13 C14 H3 120.6 . . ? C5 C14 H3 120.6 . . ? C1 C15 C16 120.5(2) . . ? C1 C15 H8 119.7 . . ? C16 C15 H8 119.7 . . ? C15 C16 C4 118.8(2) . . ? C15 C16 H7 120.6 . . ? C4 C16 H7 120.6 . . ? F5 C17 C18 118.5(2) . . ? F5 C17 C12 119.3(2) . . ? C18 C17 C12 122.2(2) . . ? F6 C18 C17 120.7(2) . . ? F6 C18 C9 119.9(2) . . ? C17 C18 C9 119.4(2) . . ? F9 C19 F7 108.6(2) . . ? F9 C19 F8 107.0(2) . . ? F7 C19 F8 106.9(2) . . ? F9 C19 S1 111.24(19) . . ? F7 C19 S1 111.00(18) . . ? F8 C19 S1 111.94(17) . . ? O1 S1 O3 115.39(10) . . ? O1 S1 O2 114.54(10) . . ? O3 S1 O2 114.67(10) . . ? O1 S1 C19 103.67(12) . . ? O3 S1 C19 103.70(11) . . ? O2 S1 C19 102.55(11) . . ? F4 P1 C4 108.23(9) . . ? F4 P1 C5 105.05(9) . . ? C4 P1 C5 113.69(11) . . ? F4 P1 C12 103.97(9) . . ? C4 P1 C12 112.28(10) . . ? C5 P1 C12 112.77(10) . . ? 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 C15 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C16 0.0(3) . . . . ? C2 C3 C4 P1 178.40(18) . . . . ? C14 C5 C6 C7 0.0(4) . . . . ? P1 C5 C6 C7 177.36(19) . . . . ? C5 C6 C7 C8 0.6(4) . . . . ? C6 C7 C8 C13 -0.4(4) . . . . ? F1 C9 C10 F2 0.3(3) . . . . ? C18 C9 C10 F2 -180.0(2) . . . . ? F1 C9 C10 C11 178.8(2) . . . . ? C18 C9 C10 C11 -1.5(4) . . . . ? F2 C10 C11 F3 -0.8(3) . . . . ? C9 C10 C11 F3 -179.3(2) . . . . ? F2 C10 C11 C12 178.80(19) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? F3 C11 C12 C17 -179.16(18) . . . . ? C10 C11 C12 C17 1.2(3) . . . . ? F3 C11 C12 P1 2.6(3) . . . . ? C10 C11 C12 P1 -177.05(17) . . . . ? C7 C8 C13 C14 -0.4(4) . . . . ? C8 C13 C14 C5 0.9(4) . . . . ? C6 C5 C14 C13 -0.7(4) . . . . ? P1 C5 C14 C13 -178.1(2) . . . . ? C2 C1 C15 C16 0.8(4) . . . . ? C1 C15 C16 C4 -1.1(3) . . . . ? C3 C4 C16 C15 0.6(3) . . . . ? P1 C4 C16 C15 -177.72(18) . . . . ? C11 C12 C17 F5 178.36(18) . . . . ? P1 C12 C17 F5 -3.3(3) . . . . ? C11 C12 C17 C18 -1.6(3) . . . . ? P1 C12 C17 C18 176.67(18) . . . . ? F5 C17 C18 F6 0.0(3) . . . . ? C12 C17 C18 F6 180.0(2) . . . . ? F5 C17 C18 C9 -179.5(2) . . . . ? C12 C17 C18 C9 0.5(3) . . . . ? F1 C9 C18 F6 1.3(3) . . . . ? C10 C9 C18 F6 -178.4(2) . . . . ? F1 C9 C18 C17 -179.2(2) . . . . ? C10 C9 C18 C17 1.1(4) . . . . ? F9 C19 S1 O1 61.4(2) . . . . ? F7 C19 S1 O1 -59.6(2) . . . . ? F8 C19 S1 O1 -178.93(17) . . . . ? F9 C19 S1 O3 -177.66(17) . . . . ? F7 C19 S1 O3 61.3(2) . . . . ? F8 C19 S1 O3 -58.0(2) . . . . ? F9 C19 S1 O2 -58.0(2) . . . . ? F7 C19 S1 O2 -179.05(19) . . . . ? F8 C19 S1 O2 61.6(2) . . . . ? C16 C4 P1 F4 106.98(18) . . . . ? C3 C4 P1 F4 -71.43(19) . . . . ? C16 C4 P1 C5 -136.73(18) . . . . ? C3 C4 P1 C5 44.9(2) . . . . ? C16 C4 P1 C12 -7.2(2) . . . . ? C3 C4 P1 C12 174.39(17) . . . . ? C14 C5 P1 F4 -38.9(2) . . . . ? C6 C5 P1 F4 143.65(18) . . . . ? C14 C5 P1 C4 -157.01(17) . . . . ? C6 C5 P1 C4 25.5(2) . . . . ? C14 C5 P1 C12 73.7(2) . . . . ? C6 C5 P1 C12 -103.8(2) . . . . ? C11 C12 P1 F4 140.15(17) . . . . ? C17 C12 P1 F4 -38.04(19) . . . . ? C11 C12 P1 C4 -103.08(19) . . . . ? C17 C12 P1 C4 78.72(19) . . . . ? C11 C12 P1 C5 26.9(2) . . . . ? C17 C12 P1 C5 -151.28(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.58 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.425 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.063