# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name R.T.Paine _publ_contact_author_address ;Department of Chemistry University of New Mexico Albuquerque, New Mexico 87131 USA ; _publ_contact_author_email rtpaine@unm.edu _publ_contact_author_phone 505.277.1661 _publ_contact_author_fax 505.277.2609 loop_ _publ_author_name _publ_author_address R.T.Paine ;Department of Chemistry University of New Mexico Albuquerque New Mexico 87131 USA ; E.N.Duesler ;Department of Chemistry University of New Mexico Albuquerque New Mexico 87131 USA ; B.P.Hay ;Department of Chemistry University of New Mexico Albuquerque New Mexico 87131 USA ; 'John R. Klaehn' ;Department of Chemistry University of New Mexico Albuquerque New Mexico 87131 USA ; M.E.McIlwain ;Idaho National Laboratory P.O. Box 1625 Idaho Falls ID 83415 USA ; ; S.Pailloux ; ;Idaho National Laboratory P.O. Box 1625 Idaho Falls ID 83415 USA ; 'Alisha D. Ray' ;Chemical Sciences Division Oak Ridge National Laboratory P.O. Box 2008 Oak Ridge, TN 37831-6119 USA ; C.E.Shirima '' 'Karen Ann Smith' '' data_rpec17 _database_code_depnum_ccdc_archive 'CCDC 715682' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H29 F6 N6 O13.50 P Yb' _chemical_formula_sum 'C26 H29 F6 N6 O13.50 P Yb' _chemical_formula_weight 959.56 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' N N 0.0061 0.0033 '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' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 29.2303(17) _cell_length_b 13.5964(8) _cell_length_c 21.6915(12) _cell_angle_alpha 90.00 _cell_angle_beta 124.507(2) _cell_angle_gamma 90.00 _cell_volume 7104.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used 7966 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 31.90 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3792 _exptl_absorpt_coefficient_mu 2.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.720 _exptl_absorpt_correction_T_max 0.780 _exptl_absorpt_process_details Bruker,SADABS _exptl_special_details ; 0.5 deg wide omega and phi scans, detector distance 5.2cm 25s/frame, 26h data collection ; _diffrn_ambient_temperature 225(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 100265 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 32.70 _reflns_number_total 13060 _reflns_number_gt 11012 _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. RPEC17 disorder on CF3 units. each F occupies 2 positions partially; the sum of each Fn+Fn'=100%. C13 F1,F2,F3/F4,F5,F6[77%/23%] C20 F7,F8,F9/F10,F11,F12[75%/25%] ; _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^)+(0.0245P)^2^+4.1273P] 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 13060 _refine_ls_number_parameters 554 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0463 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.005 _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 Yb Yb 0.744948(3) 0.987376(5) 0.930220(3) 0.02443(2) Uani 1 1 d . . . P P 0.664887(15) 0.93576(3) 1.00268(2) 0.02396(7) Uani 1 1 d . . . O1 O 0.68510(5) 0.99468(8) 0.96404(7) 0.0282(2) Uani 1 1 d . . . O2 O 0.79440(5) 0.89281(8) 1.03418(6) 0.0308(2) Uani 1 1 d . . . O3 O 0.70399(5) 1.12973(9) 0.87065(7) 0.0372(3) Uani 1 1 d . . . O4 O 0.75698(7) 0.98813(11) 0.82921(8) 0.0532(4) Uani 1 1 d . . . O5 O 0.80678(7) 0.88678(10) 0.91784(9) 0.0500(4) Uani 1 1 d . . . O6 O 0.81452(9) 0.89458(15) 0.82439(12) 0.0829(6) Uani 1 1 d . . . O7 O 0.65344(6) 0.94212(9) 0.81502(7) 0.0408(3) Uani 1 1 d . . . O8 O 0.70280(5) 0.82726(9) 0.89205(7) 0.0389(3) Uani 1 1 d . . . O9 O 0.62505(6) 0.79137(11) 0.78758(8) 0.0523(4) Uani 1 1 d . . . O10 O 0.82470(6) 1.08620(11) 0.97134(8) 0.0478(3) Uani 1 1 d . . . O11 O 0.78696(6) 1.10795(10) 1.03103(8) 0.0430(3) Uani 1 1 d . . . O12 O 0.85538(8) 1.20141(14) 1.05444(12) 0.0794(6) Uani 1 1 d . . . N1 N 0.80682(5) 0.90632(9) 1.10289(7) 0.0271(2) Uani 1 1 d . . . N2 N 0.79329(7) 0.92225(12) 0.85591(10) 0.0441(4) Uani 1 1 d . . . N3 N 0.65900(6) 0.85165(10) 0.82999(8) 0.0313(3) Uani 1 1 d . . . N4 N 0.82341(7) 1.13404(12) 1.02049(10) 0.0455(4) Uani 1 1 d . . . N5 N 0.63208(7) 1.23175(11) 0.79859(9) 0.0379(3) Uani 1 1 d . . . C1 C 0.85811(7) 0.93925(13) 1.15639(10) 0.0369(4) Uani 1 1 d . . . H1 H 0.8833 0.9543 1.1439 0.044 Uiso 1 1 calc R . . C2 C 0.87399(8) 0.95101(14) 1.22889(10) 0.0445(4) Uani 1 1 d . . . H2 H 0.9099 0.9731 1.2660 0.053 Uiso 1 1 calc R . . C3 C 0.83680(9) 0.93010(14) 1.24663(10) 0.0449(4) Uani 1 1 d . . . H3 H 0.8468 0.9388 1.2958 0.054 Uiso 1 1 calc R . . C4 C 0.78457(8) 0.89618(13) 1.19142(9) 0.0375(4) Uani 1 1 d . . . H4 H 0.7588 0.8822 1.2031 0.045 Uiso 1 1 calc R . . C5 C 0.76970(6) 0.88253(11) 1.11892(8) 0.0274(3) Uani 1 1 d . . . C6 C 0.71528(6) 0.84057(11) 1.05814(8) 0.0268(3) Uani 1 1 d . . . H6A H 0.7009 0.7985 1.0802 0.032 Uiso 1 1 calc R . . H6B H 0.7206 0.7996 1.0256 0.032 Uiso 1 1 calc R . . C7 C 0.66109(7) 1.01793(12) 1.06610(9) 0.0295(3) Uani 1 1 d . . . C8 C 0.63947(8) 0.99881(14) 1.10864(10) 0.0385(4) Uani 1 1 d . A . C9 C 0.64197(10) 1.07218(18) 1.15542(11) 0.0541(6) Uani 1 1 d . . . H9 H 0.6276 1.0597 1.1839 0.065 Uiso 1 1 calc R . . C10 C 0.66500(11) 1.16196(18) 1.16059(12) 0.0590(6) Uani 1 1 d . . . H10 H 0.6662 1.2104 1.1924 0.071 Uiso 1 1 calc R . . C11 C 0.68638(10) 1.18166(16) 1.11961(12) 0.0524(5) Uani 1 1 d . . . H11 H 0.7023 1.2433 1.1232 0.063 Uiso 1 1 calc R . . C12 C 0.68432(8) 1.10965(13) 1.07271(10) 0.0391(4) Uani 1 1 d . . . H12 H 0.6990 1.1234 1.0447 0.047 Uiso 1 1 calc R . . C13 C 0.61186(11) 0.90439(19) 1.10518(15) 0.0575(6) Uani 1 1 d . . . F1 F 0.6049(2) 0.8929(6) 1.1596(3) 0.0774(14) Uani 0.77 1 d P A 1 F2 F 0.63508(13) 0.82477(19) 1.1008(2) 0.0676(8) Uani 0.77 1 d P A 1 F3 F 0.55850(9) 0.8985(2) 1.04023(16) 0.0695(7) Uani 0.77 1 d P A 1 F4 F 0.6639(5) 0.8430(9) 1.1611(11) 0.154(6) Uani 0.23 1 d P A 2 F5 F 0.5972(11) 0.8553(11) 1.0597(8) 0.170(9) Uani 0.23 1 d P A 2 F6 F 0.5954(7) 0.903(2) 1.1472(13) 0.083(6) Uani 0.23 1 d P A 2 C14 C 0.59987(6) 0.87357(12) 0.93718(9) 0.0295(3) Uani 1 1 d . . . C15 C 0.54800(7) 0.91981(14) 0.88799(10) 0.0379(4) Uani 1 1 d . B . C16 C 0.50176(8) 0.86367(19) 0.83888(12) 0.0525(5) Uani 1 1 d . . . H16 H 0.4674 0.8949 0.8065 0.063 Uiso 1 1 calc R . . C17 C 0.50511(9) 0.76320(19) 0.83658(13) 0.0570(6) Uani 1 1 d . . . H17 H 0.4733 0.7263 0.8026 0.068 Uiso 1 1 calc R . . C18 C 0.55481(8) 0.71687(17) 0.88378(13) 0.0530(5) Uani 1 1 d . . . H18 H 0.5571 0.6480 0.8828 0.064 Uiso 1 1 calc R . . C19 C 0.60179(7) 0.77176(14) 0.93310(11) 0.0405(4) Uani 1 1 d . . . H19 H 0.6359 0.7392 0.9646 0.049 Uiso 1 1 calc R . . C20 C 0.53886(9) 1.02852(18) 0.88767(16) 0.0578(6) Uani 1 1 d . . . F7 F 0.53053(12) 1.05383(18) 0.94359(15) 0.0733(6) Uani 0.75 1 d P B 1 F8 F 0.5817(2) 1.0841(4) 0.9067(3) 0.0603(13) Uani 0.75 1 d P B 1 F9 F 0.49494(12) 1.0623(2) 0.82726(16) 0.0839(10) Uani 0.75 1 d P B 1 F10 F 0.5296(6) 1.0507(6) 0.8096(4) 0.132(4) Uani 0.25 1 d P B 2 F11 F 0.4964(5) 1.0479(7) 0.8723(12) 0.149(7) Uani 0.25 1 d P B 2 F12 F 0.5791(6) 1.0809(10) 0.9200(9) 0.069(4) Uani 0.25 1 d P B 2 C21 C 0.65538(8) 1.15561(13) 0.84260(11) 0.0379(4) Uani 1 1 d . . . H21 H 0.6339 1.1181 0.8536 0.045 Uiso 1 1 calc R . . C22 C 0.66352(11) 1.29352(17) 0.78159(15) 0.0610(6) Uani 1 1 d . . . H22A H 0.6821 1.3445 0.8193 0.092 Uiso 1 1 calc R . . H22B H 0.6387 1.3236 0.7329 0.092 Uiso 1 1 calc R . . H22C H 0.6910 1.2541 0.7811 0.092 Uiso 1 1 calc R . . C23 C 0.57571(10) 1.26102(18) 0.77021(15) 0.0623(6) Uani 1 1 d . . . H23A H 0.5596 1.2141 0.7865 0.093 Uiso 1 1 calc R . . H23B H 0.5538 1.2628 0.7160 0.093 Uiso 1 1 calc R . . H23C H 0.5760 1.3258 0.7892 0.093 Uiso 1 1 calc R . . O13 O 0.50524(11) 0.4489(2) 0.63434(12) 0.1096(8) Uani 1 1 d . . . N6 N 0.48958(10) 0.3658(2) 0.53486(14) 0.0794(7) Uani 1 1 d . . . C24 C 0.47572(13) 0.4015(3) 0.57818(17) 0.0861(9) Uani 1 1 d . . . H24 H 0.4394 0.3889 0.5642 0.103 Uiso 1 1 calc R . . C25 C 0.54410(15) 0.3826(3) 0.5522(2) 0.1095(13) Uani 1 1 d . . . H25A H 0.5660 0.4188 0.5988 0.164 Uiso 1 1 calc R . . H25B H 0.5414 0.4203 0.5123 0.164 Uiso 1 1 calc R . . H25C H 0.5618 0.3200 0.5572 0.164 Uiso 1 1 calc R . . C26 C 0.45146(19) 0.3075(4) 0.4690(3) 0.160(2) Uani 1 1 d . . . H26A H 0.4689 0.2455 0.4715 0.239 Uiso 1 1 calc R . . H26B H 0.4420 0.3431 0.4245 0.239 Uiso 1 1 calc R . . H26C H 0.4180 0.2948 0.4670 0.239 Uiso 1 1 calc R . . O14 O 0.5000 0.5257(19) 0.7500 0.072(15) Uani 0.34 2 d SP . . O15 O 0.4836(17) 0.5123(14) 0.727(2) 0.087(7) Uani 0.33 1 d P . . H1W H 0.497(2) 0.489(3) 0.711(3) 0.105(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb 0.02623(3) 0.02483(3) 0.02695(3) 0.00264(2) 0.01790(3) 0.00307(2) P 0.02212(17) 0.02761(18) 0.02497(16) 0.00430(13) 0.01503(14) 0.00522(13) O1 0.0298(5) 0.0305(5) 0.0322(5) 0.0072(4) 0.0222(5) 0.0069(4) O2 0.0298(5) 0.0368(6) 0.0272(5) 0.0048(4) 0.0169(5) 0.0066(4) O3 0.0426(7) 0.0295(6) 0.0455(7) 0.0089(5) 0.0286(6) 0.0081(5) O4 0.0584(10) 0.0718(10) 0.0406(8) 0.0107(7) 0.0348(8) 0.0221(7) O5 0.0710(10) 0.0400(7) 0.0697(9) 0.0151(7) 0.0581(9) 0.0175(7) O6 0.1184(16) 0.0881(14) 0.1036(15) 0.0126(11) 0.0997(14) 0.0298(12) O7 0.0491(8) 0.0342(6) 0.0307(6) 0.0068(5) 0.0175(6) 0.0047(5) O8 0.0308(6) 0.0317(6) 0.0342(6) 0.0007(5) 0.0065(5) 0.0064(5) O9 0.0390(7) 0.0442(8) 0.0465(8) -0.0090(6) 0.0079(6) -0.0079(6) O10 0.0459(8) 0.0514(8) 0.0593(9) -0.0189(7) 0.0377(7) -0.0151(6) O11 0.0502(8) 0.0421(7) 0.0455(7) -0.0049(6) 0.0324(7) -0.0034(6) O12 0.0811(13) 0.0719(12) 0.0932(14) -0.0469(11) 0.0542(12) -0.0428(10) N1 0.0242(6) 0.0270(6) 0.0265(6) 0.0025(5) 0.0123(5) 0.0042(4) N2 0.0553(10) 0.0426(8) 0.0581(10) -0.0034(7) 0.0464(9) 0.0009(7) N3 0.0281(7) 0.0343(7) 0.0292(6) -0.0003(5) 0.0148(6) 0.0025(5) N4 0.0457(9) 0.0412(9) 0.0494(9) -0.0120(7) 0.0268(8) -0.0093(7) N5 0.0452(9) 0.0296(7) 0.0392(8) 0.0075(6) 0.0241(7) 0.0068(6) C1 0.0264(8) 0.0345(9) 0.0408(9) 0.0016(7) 0.0136(7) 0.0006(6) C2 0.0355(9) 0.0374(9) 0.0364(9) -0.0057(7) 0.0059(8) 0.0013(7) C3 0.0508(11) 0.0436(10) 0.0264(8) -0.0034(7) 0.0137(8) 0.0102(8) C4 0.0401(9) 0.0429(9) 0.0294(8) 0.0058(7) 0.0197(7) 0.0123(7) C5 0.0258(7) 0.0278(7) 0.0259(7) 0.0046(5) 0.0130(6) 0.0068(5) C6 0.0238(7) 0.0277(7) 0.0279(7) 0.0051(5) 0.0141(6) 0.0039(5) C7 0.0281(7) 0.0357(8) 0.0270(7) 0.0038(6) 0.0169(6) 0.0092(6) C8 0.0428(10) 0.0488(10) 0.0327(8) 0.0094(7) 0.0266(8) 0.0145(7) C9 0.0687(14) 0.0699(15) 0.0383(10) 0.0039(9) 0.0391(11) 0.0191(11) C10 0.0752(16) 0.0589(14) 0.0409(11) -0.0103(9) 0.0317(11) 0.0141(11) C11 0.0605(13) 0.0452(11) 0.0485(11) -0.0101(9) 0.0291(10) 0.0011(9) C12 0.0422(10) 0.0378(9) 0.0403(9) -0.0021(7) 0.0252(8) 0.0027(7) C13 0.0762(16) 0.0618(14) 0.0685(15) 0.0136(12) 0.0614(14) 0.0109(12) F1 0.117(3) 0.087(2) 0.0702(18) 0.0200(17) 0.078(2) 0.008(2) F2 0.086(2) 0.0482(11) 0.115(3) 0.0124(16) 0.085(2) 0.0079(13) F3 0.0517(11) 0.0868(18) 0.0723(14) 0.0064(12) 0.0365(11) -0.0119(10) F4 0.100(8) 0.097(8) 0.279(17) 0.115(11) 0.115(10) 0.040(6) F5 0.36(3) 0.110(12) 0.108(11) -0.059(9) 0.175(17) -0.148(15) F6 0.065(6) 0.116(12) 0.121(13) 0.005(9) 0.085(8) -0.005(6) C14 0.0236(7) 0.0382(8) 0.0275(7) 0.0019(6) 0.0148(6) 0.0030(6) C15 0.0258(8) 0.0503(10) 0.0342(8) 0.0098(7) 0.0149(7) 0.0049(7) C16 0.0274(9) 0.0706(15) 0.0441(11) 0.0065(10) 0.0111(8) 0.0012(9) C17 0.0339(10) 0.0715(15) 0.0495(12) -0.0145(11) 0.0141(9) -0.0126(10) C18 0.0392(11) 0.0494(12) 0.0628(13) -0.0174(10) 0.0244(10) -0.0074(8) C19 0.0280(8) 0.0413(9) 0.0465(10) -0.0061(7) 0.0176(8) 0.0026(7) C20 0.0307(10) 0.0558(13) 0.0706(16) 0.0236(12) 0.0188(11) 0.0141(9) F7 0.0887(17) 0.0634(13) 0.1042(17) 0.0082(13) 0.0764(15) 0.0220(13) F8 0.0457(19) 0.0489(17) 0.093(3) 0.0189(18) 0.043(2) 0.0113(12) F9 0.0517(15) 0.0769(18) 0.0661(16) 0.0279(13) -0.0007(11) 0.0279(13) F10 0.256(13) 0.060(4) 0.055(4) 0.015(3) 0.072(6) -0.020(6) F11 0.077(7) 0.065(5) 0.34(2) 0.028(11) 0.140(12) 0.035(5) F12 0.063(8) 0.037(5) 0.046(4) -0.009(3) -0.005(4) 0.025(5) C21 0.0456(10) 0.0299(8) 0.0466(10) 0.0105(7) 0.0313(9) 0.0076(7) C22 0.0707(15) 0.0446(12) 0.0767(16) 0.0268(11) 0.0470(14) 0.0077(10) C23 0.0505(13) 0.0528(13) 0.0740(16) 0.0206(11) 0.0296(12) 0.0190(10) O13 0.1055(19) 0.136(2) 0.0564(12) -0.0225(14) 0.0275(13) -0.0279(17) N6 0.0604(14) 0.0856(17) 0.0665(14) -0.0103(13) 0.0205(12) -0.0044(12) C24 0.0644(18) 0.110(3) 0.0653(18) -0.0037(17) 0.0256(16) -0.0150(17) C25 0.078(2) 0.115(3) 0.127(3) 0.015(3) 0.052(2) 0.019(2) C26 0.119(4) 0.192(6) 0.118(4) -0.087(4) 0.037(3) -0.031(4) O14 0.10(5) 0.048(6) 0.10(4) 0.000 0.07(4) 0.000 O15 0.074(13) 0.110(11) 0.090(17) 0.034(13) 0.054(13) 0.036(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Yb O1 2.2499(11) . ? Yb O3 2.2575(11) . ? Yb O2 2.2660(11) . ? Yb O10 2.3831(13) . ? Yb O5 2.3997(13) . ? Yb O8 2.4055(12) . ? Yb O4 2.4079(14) . ? Yb O11 2.4362(13) . ? Yb O7 2.4908(13) . ? P O1 1.5016(11) . ? P C6 1.8123(14) . ? P C14 1.8127(17) . ? P C7 1.8236(16) . ? O2 N1 1.3318(16) . ? O3 C21 1.238(2) . ? O4 N2 1.252(2) . ? O5 N2 1.262(2) . ? O6 N2 1.2145(19) . ? O7 N3 1.2591(18) . ? O8 N3 1.2682(17) . ? O9 N3 1.2118(19) . ? O10 N4 1.267(2) . ? O11 N4 1.261(2) . ? O12 N4 1.215(2) . ? N1 C1 1.351(2) . ? N1 C5 1.353(2) . ? N5 C21 1.308(2) . ? N5 C22 1.439(3) . ? N5 C23 1.450(3) . ? C1 C2 1.374(3) . ? C1 H1 0.9400 . ? C2 C3 1.373(3) . ? C2 H2 0.9400 . ? C3 C4 1.381(3) . ? C3 H3 0.9400 . ? C4 C5 1.386(2) . ? C4 H4 0.9400 . ? C5 C6 1.489(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C12 1.388(2) . ? C7 C8 1.407(2) . ? C8 C9 1.395(3) . ? C8 C13 1.495(3) . ? C9 C10 1.368(4) . ? C9 H9 0.9400 . ? C10 C11 1.372(3) . ? C10 H10 0.9400 . ? C11 C12 1.388(3) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C13 F5 1.060(10) . ? C13 F6 1.249(16) . ? C13 F2 1.310(3) . ? C13 F1 1.316(5) . ? C13 F3 1.391(4) . ? C13 F4 1.547(11) . ? C14 C19 1.390(2) . ? C14 C15 1.414(2) . ? C15 C16 1.383(3) . ? C15 C20 1.501(3) . ? C16 C17 1.372(3) . ? C16 H16 0.9400 . ? C17 C18 1.368(3) . ? C17 H17 0.9400 . ? C18 C19 1.386(3) . ? C18 H18 0.9400 . ? C19 H19 0.9400 . ? C20 F11 1.119(7) . ? C20 F12 1.203(14) . ? C20 F9 1.293(3) . ? C20 F8 1.312(5) . ? C20 F7 1.408(4) . ? C20 F10 1.585(8) . ? C21 H21 0.9400 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? O13 C24 1.206(4) . ? N6 C24 1.309(4) . ? N6 C25 1.433(4) . ? N6 C26 1.452(4) . ? C24 H24 0.9400 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 H25C 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 H26C 0.9700 . ? O14 O15 0.49(3) 2_656 ? O14 H1W 0.94(5) . ? O15 O15 0.91(8) 2_656 ? O15 H1W 0.72(6) . ? 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 Yb O3 83.72(4) . . ? O1 Yb O2 82.88(4) . . ? O3 Yb O2 152.69(4) . . ? O1 Yb O10 129.01(4) . . ? O3 Yb O10 79.63(5) . . ? O2 Yb O10 90.59(5) . . ? O1 Yb O5 146.67(4) . . ? O3 Yb O5 127.84(4) . . ? O2 Yb O5 72.04(4) . . ? O10 Yb O5 73.99(5) . . ? O1 Yb O8 79.11(4) . . ? O3 Yb O8 125.22(4) . . ? O2 Yb O8 75.08(4) . . ? O10 Yb O8 147.21(5) . . ? O5 Yb O8 73.56(5) . . ? O1 Yb O4 146.92(5) . . ? O3 Yb O4 77.23(5) . . ? O2 Yb O4 124.63(4) . . ? O10 Yb O4 73.86(5) . . ? O5 Yb O4 52.63(5) . . ? O8 Yb O4 90.05(5) . . ? O1 Yb O11 76.54(4) . . ? O3 Yb O11 76.76(5) . . ? O2 Yb O11 77.03(5) . . ? O10 Yb O11 52.83(4) . . ? O5 Yb O11 117.09(5) . . ? O8 Yb O11 144.82(4) . . ? O4 Yb O11 123.69(5) . . ? O1 Yb O7 75.32(4) . . ? O3 Yb O7 73.60(4) . . ? O2 Yb O7 125.12(4) . . ? O10 Yb O7 141.40(5) . . ? O5 Yb O7 101.29(5) . . ? O8 Yb O7 51.80(4) . . ? O4 Yb O7 73.47(5) . . ? O11 Yb O7 140.85(4) . . ? O1 P C6 108.82(7) . . ? O1 P C14 112.37(7) . . ? C6 P C14 106.51(7) . . ? O1 P C7 107.80(7) . . ? C6 P C7 108.10(7) . . ? C14 P C7 113.10(7) . . ? P O1 Yb 141.54(6) . . ? N1 O2 Yb 130.63(9) . . ? C21 O3 Yb 127.86(11) . . ? N2 O4 Yb 95.65(11) . . ? N2 O5 Yb 95.76(10) . . ? N3 O7 Yb 94.26(9) . . ? N3 O8 Yb 98.10(9) . . ? N4 O10 Yb 96.62(10) . . ? N4 O11 Yb 94.27(10) . . ? O2 N1 C1 118.26(14) . . ? O2 N1 C5 120.32(12) . . ? C1 N1 C5 121.33(14) . . ? O6 N2 O4 122.06(18) . . ? O6 N2 O5 121.99(18) . . ? O4 N2 O5 115.95(14) . . ? O9 N3 O7 122.30(14) . . ? O9 N3 O8 121.95(15) . . ? O7 N3 O8 115.74(14) . . ? O12 N4 O11 122.76(18) . . ? O12 N4 O10 121.19(18) . . ? O11 N4 O10 116.05(15) . . ? C21 N5 C22 120.33(17) . . ? C21 N5 C23 121.59(17) . . ? C22 N5 C23 117.91(17) . . ? N1 C1 C2 120.86(17) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C3 C2 C1 119.29(17) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.22(17) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.71(17) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N1 C5 C4 118.55(15) . . ? N1 C5 C6 118.29(13) . . ? C4 C5 C6 123.14(15) . . ? C5 C6 P 111.89(10) . . ? C5 C6 H6A 109.2 . . ? P C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? P C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C12 C7 C8 118.27(16) . . ? C12 C7 P 113.14(12) . . ? C8 C7 P 128.57(14) . . ? C9 C8 C7 119.15(19) . . ? C9 C8 C13 117.05(18) . . ? C7 C8 C13 123.77(17) . . ? C10 C9 C8 121.2(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.32(19) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C7 C12 C11 121.66(18) . . ? C7 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? F5 C13 F6 123.5(15) . . ? F2 C13 F1 108.5(4) . . ? F2 C13 F3 102.0(3) . . ? F1 C13 F3 104.4(3) . . ? F5 C13 C8 120.7(5) . . ? F6 C13 C8 113.2(13) . . ? F2 C13 C8 115.2(2) . . ? F1 C13 C8 114.2(4) . . ? F3 C13 C8 111.4(2) . . ? F5 C13 F4 95.1(14) . . ? F6 C13 F4 92.0(12) . . ? F2 C13 F4 44.8(7) . . ? F1 C13 F4 79.4(7) . . ? F3 C13 F4 143.5(7) . . ? C8 C13 F4 99.2(5) . . ? C19 C14 C15 117.34(16) . . ? C19 C14 P 116.89(12) . . ? C15 C14 P 125.72(14) . . ? C16 C15 C14 119.88(18) . . ? C16 C15 C20 116.48(18) . . ? C14 C15 C20 123.58(17) . . ? C17 C16 C15 121.23(19) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C18 C17 C16 119.9(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 119.8(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 121.80(18) . . ? C18 C19 H19 119.1 . . ? C14 C19 H19 119.1 . . ? F11 C20 F12 126.0(10) . . ? F9 C20 F8 109.7(4) . . ? F9 C20 F7 103.2(2) . . ? F8 C20 F7 100.8(3) . . ? F11 C20 C15 113.4(6) . . ? F12 C20 C15 117.8(7) . . ? F9 C20 C15 115.3(3) . . ? F8 C20 C15 115.5(3) . . ? F7 C20 C15 110.7(2) . . ? F11 C20 F10 98.4(11) . . ? F12 C20 F10 91.7(9) . . ? C15 C20 F10 96.6(4) . . ? O3 C21 N5 124.18(17) . . ? O3 C21 H21 117.9 . . ? N5 C21 H21 117.9 . . ? N5 C22 H22A 109.5 . . ? N5 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N5 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N5 C23 H23A 109.5 . . ? N5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C24 N6 C25 120.2(3) . . ? C24 N6 C26 122.1(3) . . ? C25 N6 C26 117.7(3) . . ? O13 C24 N6 126.0(3) . . ? O13 C24 H24 117.0 . . ? N6 C24 H24 117.0 . . ? N6 C25 H25A 109.5 . . ? N6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O15 O14 H1W 105(7) 2_656 . ? O15 O15 H1W 91(8) 2_656 . ? 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 C6 P O1 Yb 18.78(14) . . . . ? C14 P O1 Yb -98.92(12) . . . . ? C7 P O1 Yb 135.79(11) . . . . ? O3 Yb O1 P 173.06(12) . . . . ? O2 Yb O1 P -30.78(12) . . . . ? O10 Yb O1 P -115.74(12) . . . . ? O5 Yb O1 P 10.13(18) . . . . ? O8 Yb O1 P 45.32(12) . . . . ? O4 Yb O1 P 118.25(12) . . . . ? O11 Yb O1 P -109.09(12) . . . . ? O7 Yb O1 P 98.41(12) . . . . ? O1 Yb O2 N1 -46.24(12) . . . . ? O3 Yb O2 N1 14.92(18) . . . . ? O10 Yb O2 N1 83.04(12) . . . . ? O5 Yb O2 N1 155.99(13) . . . . ? O8 Yb O2 N1 -126.81(13) . . . . ? O4 Yb O2 N1 153.72(11) . . . . ? O11 Yb O2 N1 31.52(12) . . . . ? O7 Yb O2 N1 -112.66(12) . . . . ? O1 Yb O3 C21 -30.99(15) . . . . ? O2 Yb O3 C21 -91.97(18) . . . . ? O10 Yb O3 C21 -162.58(16) . . . . ? O5 Yb O3 C21 137.23(15) . . . . ? O8 Yb O3 C21 40.93(17) . . . . ? O4 Yb O3 C21 121.79(16) . . . . ? O11 Yb O3 C21 -108.59(16) . . . . ? O7 Yb O3 C21 45.52(15) . . . . ? O1 Yb O4 N2 -139.01(10) . . . . ? O3 Yb O4 N2 164.58(13) . . . . ? O2 Yb O4 N2 2.63(14) . . . . ? O10 Yb O4 N2 81.86(12) . . . . ? O5 Yb O4 N2 -0.08(11) . . . . ? O8 Yb O4 N2 -69.18(12) . . . . ? O11 Yb O4 N2 100.25(12) . . . . ? O7 Yb O4 N2 -118.99(12) . . . . ? O1 Yb O5 N2 139.33(11) . . . . ? O3 Yb O5 N2 -18.98(14) . . . . ? O2 Yb O5 N2 -177.57(13) . . . . ? O10 Yb O5 N2 -81.59(12) . . . . ? O8 Yb O5 N2 103.18(12) . . . . ? O4 Yb O5 N2 0.08(11) . . . . ? O11 Yb O5 N2 -113.09(12) . . . . ? O7 Yb O5 N2 58.93(12) . . . . ? O1 Yb O7 N3 -89.31(9) . . . . ? O3 Yb O7 N3 -176.98(10) . . . . ? O2 Yb O7 N3 -19.25(11) . . . . ? O10 Yb O7 N3 135.05(9) . . . . ? O5 Yb O7 N3 56.63(10) . . . . ? O8 Yb O7 N3 -1.75(9) . . . . ? O4 Yb O7 N3 101.82(10) . . . . ? O11 Yb O7 N3 -134.67(9) . . . . ? O1 Yb O8 N3 81.56(10) . . . . ? O3 Yb O8 N3 7.36(12) . . . . ? O2 Yb O8 N3 167.00(10) . . . . ? O10 Yb O8 N3 -126.20(10) . . . . ? O5 Yb O8 N3 -117.71(10) . . . . ? O4 Yb O8 N3 -66.99(10) . . . . ? O11 Yb O8 N3 128.37(10) . . . . ? O7 Yb O8 N3 1.75(9) . . . . ? O1 Yb O10 N4 5.33(14) . . . . ? O3 Yb O10 N4 78.40(12) . . . . ? O2 Yb O10 N4 -75.96(12) . . . . ? O5 Yb O10 N4 -147.08(13) . . . . ? O8 Yb O10 N4 -138.61(11) . . . . ? O4 Yb O10 N4 157.97(13) . . . . ? O11 Yb O10 N4 -2.79(11) . . . . ? O7 Yb O10 N4 124.82(12) . . . . ? O1 Yb O11 N4 -170.73(12) . . . . ? O3 Yb O11 N4 -84.13(11) . . . . ? O2 Yb O11 N4 103.61(11) . . . . ? O10 Yb O11 N4 2.79(11) . . . . ? O5 Yb O11 N4 41.85(12) . . . . ? O8 Yb O11 N4 141.87(11) . . . . ? O4 Yb O11 N4 -19.58(13) . . . . ? O7 Yb O11 N4 -125.69(11) . . . . ? Yb O2 N1 C1 -101.26(14) . . . . ? Yb O2 N1 C5 82.15(16) . . . . ? Yb O4 N2 O6 -179.38(19) . . . . ? Yb O4 N2 O5 0.14(18) . . . . ? Yb O5 N2 O6 179.38(19) . . . . ? Yb O5 N2 O4 -0.14(18) . . . . ? Yb O7 N3 O9 -176.33(15) . . . . ? Yb O7 N3 O8 2.90(14) . . . . ? Yb O8 N3 O9 176.21(14) . . . . ? Yb O8 N3 O7 -3.02(15) . . . . ? Yb O11 N4 O12 174.7(2) . . . . ? Yb O11 N4 O10 -4.65(18) . . . . ? Yb O10 N4 O12 -174.59(19) . . . . ? Yb O10 N4 O11 4.78(18) . . . . ? O2 N1 C1 C2 -177.51(15) . . . . ? C5 N1 C1 C2 -1.0(2) . . . . ? N1 C1 C2 C3 -0.8(3) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? O2 N1 C5 C4 178.94(13) . . . . ? C1 N1 C5 C4 2.5(2) . . . . ? O2 N1 C5 C6 0.42(19) . . . . ? C1 N1 C5 C6 -176.07(14) . . . . ? C3 C4 C5 N1 -2.2(2) . . . . ? C3 C4 C5 C6 176.23(16) . . . . ? N1 C5 C6 P -86.52(14) . . . . ? C4 C5 C6 P 95.03(16) . . . . ? O1 P C6 C5 63.54(12) . . . . ? C14 P C6 C5 -175.10(11) . . . . ? C7 P C6 C5 -53.27(13) . . . . ? O1 P C7 C12 -8.45(14) . . . . ? C6 P C7 C12 109.03(13) . . . . ? C14 P C7 C12 -133.30(13) . . . . ? O1 P C7 C8 173.23(15) . . . . ? C6 P C7 C8 -69.29(17) . . . . ? C14 P C7 C8 48.38(18) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? P C7 C8 C9 178.41(15) . . . . ? C12 C7 C8 C13 178.14(19) . . . . ? P C7 C8 C13 -3.6(3) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C13 C8 C9 C10 -178.1(2) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C8 C7 C12 C11 -0.2(3) . . . . ? P C7 C12 C11 -178.69(16) . . . . ? C10 C11 C12 C7 0.0(3) . . . . ? C9 C8 C13 F5 160.6(18) . . . . ? C7 C8 C13 F5 -17.4(18) . . . . ? C9 C8 C13 F6 -1.6(11) . . . . ? C7 C8 C13 F6 -179.6(11) . . . . ? C9 C8 C13 F2 -142.0(3) . . . . ? C7 C8 C13 F2 40.0(4) . . . . ? C9 C8 C13 F1 -15.4(4) . . . . ? C7 C8 C13 F1 166.6(3) . . . . ? C9 C8 C13 F3 102.5(2) . . . . ? C7 C8 C13 F3 -75.5(3) . . . . ? C9 C8 C13 F4 -97.8(8) . . . . ? C7 C8 C13 F4 84.2(8) . . . . ? O1 P C14 C19 109.91(14) . . . . ? C6 P C14 C19 -9.16(15) . . . . ? C7 P C14 C19 -127.76(14) . . . . ? O1 P C14 C15 -67.45(16) . . . . ? C6 P C14 C15 173.48(14) . . . . ? C7 P C14 C15 54.88(16) . . . . ? C19 C14 C15 C16 0.5(3) . . . . ? P C14 C15 C16 177.83(15) . . . . ? C19 C14 C15 C20 177.65(19) . . . . ? P C14 C15 C20 -5.0(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C20 C15 C16 C17 -177.6(2) . . . . ? C15 C16 C17 C18 0.4(4) . . . . ? C16 C17 C18 C19 -0.9(4) . . . . ? C17 C18 C19 C14 1.2(3) . . . . ? C15 C14 C19 C18 -1.0(3) . . . . ? P C14 C19 C18 -178.54(17) . . . . ? C16 C15 C20 F11 29.9(13) . . . . ? C14 C15 C20 F11 -147.4(13) . . . . ? C16 C15 C20 F12 -167.7(9) . . . . ? C14 C15 C20 F12 15.0(10) . . . . ? C16 C15 C20 F9 -21.9(4) . . . . ? C14 C15 C20 F9 160.8(3) . . . . ? C16 C15 C20 F8 -151.5(3) . . . . ? C14 C15 C20 F8 31.3(4) . . . . ? C16 C15 C20 F7 94.8(3) . . . . ? C14 C15 C20 F7 -82.5(3) . . . . ? C16 C15 C20 F10 -72.3(6) . . . . ? C14 C15 C20 F10 110.4(6) . . . . ? Yb O3 C21 N5 -168.37(14) . . . . ? C22 N5 C21 O3 -1.9(3) . . . . ? C23 N5 C21 O3 -177.1(2) . . . . ? C25 N6 C24 O13 -0.5(6) . . . . ? C26 N6 C24 O13 178.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 O13 0.94 2.42 3.354(3) 170.4 7_667 C6 H6A F2 0.98 2.24 2.975(3) 131.2 . C6 H6A O5 0.98 2.53 3.259(2) 131.0 7_667 C6 H6B O8 0.98 2.58 3.0293(18) 108.1 7_667 C9 H9 F1 0.94 2.34 2.689(8) 101.7 . C9 H9 O7 0.94 2.49 3.289(2) 142.4 6_576 C12 H12 O1 0.94 2.34 2.839(2) 112.6 . C16 H16 F9 0.94 2.37 2.710(4) 100.8 . C17 H17 O9 0.94 2.55 3.204(2) 126.9 2_656 C21 H21 F8 0.94 2.42 3.304(5) 156.7 . C21 H21 O1 0.94 2.59 3.145(2) 117.8 . C22 H22B O6 0.97 2.50 3.042(3) 114.9 4_656 C25 H25A O13 0.97 2.34 2.751(5) 104.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.70 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.882 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.069 data_rpsl20a _database_code_depnum_ccdc_archive 'CCDC 715683' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F12 N O P' _chemical_formula_sum 'C22 H12 F12 N O P' _chemical_formula_weight 565.30 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.6362(12) _cell_length_b 19.362(3) _cell_length_c 10.6850(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.192(6) _cell_angle_gamma 90.00 _cell_volume 2333.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6952 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 32.69 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details Bruker,SADABS _exptl_special_details ; omega and phi scans-widths 0.5 degrees. exposure time per frame is 20s. data collection 20 hr. detector distance 5.5cm ; _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 32662 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.13 _reflns_number_total 6258 _reflns_number_gt 4864 _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. RPSL20-disorder on CF3's each F occupies 2 positions whose occupancies total to 100% eg occupancy F1+ ocupancy F1A0% C13 F1,F2,F3/F1A,F2A,F3A 60%/40% C14 F4,F5,F6/F4A,F5A,F6A 50%/50% C21 F7,F8,F9/F7A,F8A,F9A 50%/50% ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w[\s^2^(Fo^2^)+(0.2000P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6258 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.2327 _refine_ls_wR_factor_gt 0.1970 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 0.41167(3) 0.25363(2) 0.42572(4) 0.03335(18) Uani 1 1 d . . . O1 O 0.42051(12) 0.24666(7) 0.28977(13) 0.0440(3) Uani 1 1 d . . . N1 N 0.57604(15) 0.11123(9) 0.61143(18) 0.0515(4) Uani 1 1 d . . . C1 C 0.66510(19) 0.06736(12) 0.6096(3) 0.0612(6) Uani 1 1 d . . . H1 H 0.7226 0.0596 0.6871 0.073 Uiso 1 1 calc R . . C2 C 0.6765(2) 0.03310(12) 0.5001(3) 0.0644(6) Uani 1 1 d . . . H2 H 0.7403 0.0029 0.5031 0.077 Uiso 1 1 calc R . . C3 C 0.5942(2) 0.04392(13) 0.3889(3) 0.0644(6) Uani 1 1 d . . . H3 H 0.5992 0.0204 0.3134 0.077 Uiso 1 1 calc R . . C4 C 0.50193(19) 0.09003(11) 0.3862(2) 0.0533(5) Uani 1 1 d . . . H4 H 0.4448 0.0990 0.3090 0.064 Uiso 1 1 calc R . . C5 C 0.49619(15) 0.12243(9) 0.50034(18) 0.0414(4) Uani 1 1 d . . . C6 C 0.39850(14) 0.17285(9) 0.50585(17) 0.0401(4) Uani 1 1 d . . . H6A H 0.4000 0.1821 0.5964 0.048 Uiso 1 1 calc R . . H6B H 0.3218 0.1517 0.4654 0.048 Uiso 1 1 calc R . . C7 C 0.28027(13) 0.30364(9) 0.42918(16) 0.0379(4) Uani 1 1 d . . . C8 C 0.24418(14) 0.31757(10) 0.54064(18) 0.0420(4) Uani 1 1 d . . . H8 H 0.2890 0.3019 0.6211 0.050 Uiso 1 1 calc R . . C9 C 0.14085(15) 0.35511(11) 0.5321(2) 0.0493(5) Uani 1 1 d . A . C10 C 0.07454(15) 0.37936(12) 0.4156(2) 0.0533(5) Uani 1 1 d . . . H10 H 0.0040 0.4040 0.4111 0.064 Uiso 1 1 calc R . . C11 C 0.11334(16) 0.36688(12) 0.3052(2) 0.0540(5) Uani 1 1 d . B . C12 C 0.21503(15) 0.32895(11) 0.31154(18) 0.0472(4) Uani 1 1 d . . . H12 H 0.2402 0.3202 0.2359 0.057 Uiso 1 1 calc R . . C13 C 0.1033(2) 0.37048(19) 0.6545(3) 0.0800(9) Uani 1 1 d . . . F1 F 0.1938(3) 0.4112(3) 0.7398(4) 0.0999(14) Uani 0.60 1 d P A 1 F2 F 0.0109(5) 0.4080(5) 0.6437(7) 0.128(3) Uani 0.60 1 d P A 1 F3 F 0.1025(7) 0.3191(3) 0.7279(6) 0.115(2) Uani 0.60 1 d P A 1 F1A F 0.1659(8) 0.3527(8) 0.7501(6) 0.130(4) Uani 0.40 1 d P A 2 F2A F 0.0085(12) 0.3224(7) 0.6477(13) 0.191(5) Uani 0.40 1 d P A 2 F3A F 0.0504(13) 0.4253(8) 0.6480(12) 0.168(7) Uani 0.40 1 d P A 2 C14 C 0.0484(3) 0.3978(3) 0.1782(3) 0.1033(13) Uani 1 1 d . . . F4 F 0.0934(7) 0.3855(6) 0.0843(6) 0.115(3) Uani 0.50 1 d P B 1 F5 F -0.0585(6) 0.3662(8) 0.1395(7) 0.160(4) Uani 0.50 1 d P B 1 F6 F 0.0209(18) 0.4613(5) 0.1868(8) 0.215(7) Uani 0.50 1 d P B 1 F4A F -0.0528(6) 0.4182(7) 0.1742(9) 0.139(4) Uani 0.50 1 d P B 2 F5A F 0.1097(7) 0.4559(7) 0.1548(10) 0.163(5) Uani 0.50 1 d P B 2 F6A F 0.0437(15) 0.3537(11) 0.0864(10) 0.244(8) Uani 0.50 1 d P B 2 C15 C 0.53585(12) 0.30060(8) 0.52345(15) 0.0342(3) Uani 1 1 d . . . C16 C 0.60683(13) 0.27489(10) 0.63715(16) 0.0368(4) Uani 1 1 d . . . H16 H 0.5890 0.2322 0.6700 0.044 Uiso 1 1 calc R . . C17 C 0.70499(13) 0.31279(10) 0.70253(17) 0.0415(4) Uani 1 1 d . C . C18 C 0.73049(15) 0.37582(10) 0.65716(19) 0.0464(4) Uani 1 1 d . . . H18 H 0.7968 0.4011 0.7021 0.056 Uiso 1 1 calc R . . C19 C 0.65797(15) 0.40185(10) 0.5448(2) 0.0454(4) Uani 1 1 d . . . C20 C 0.56131(14) 0.36390(9) 0.47510(18) 0.0408(4) Uani 1 1 d . . . H20 H 0.5142 0.3809 0.3968 0.049 Uiso 1 1 calc R . . C21 C 0.78285(18) 0.28334(14) 0.8240(2) 0.0571(5) Uani 1 1 d . . . F7 F 0.8924(4) 0.2950(5) 0.8465(7) 0.109(3) Uani 0.50 1 d P C 1 F8 F 0.7468(8) 0.3004(5) 0.9290(7) 0.106(3) Uani 0.50 1 d P C 1 F9 F 0.7726(5) 0.2120(2) 0.8343(6) 0.0961(19) Uani 0.50 1 d P C 1 F7A F 0.7328(6) 0.2765(6) 0.9114(7) 0.123(4) Uani 0.50 1 d P C 2 F8A F 0.8360(7) 0.2306(4) 0.7976(6) 0.132(3) Uani 0.50 1 d P C 2 F9A F 0.8715(6) 0.3288(4) 0.8689(7) 0.121(3) Uani 0.50 1 d P C 2 C22 C 0.6854(2) 0.47071(12) 0.4985(3) 0.0620(6) Uani 1 1 d . . . F10 F 0.60485(18) 0.49306(9) 0.3958(2) 0.0998(6) Uani 1 1 d . . . F11 F 0.78757(15) 0.47229(11) 0.4666(2) 0.1052(7) Uani 1 1 d . . . F12 F 0.6886(2) 0.51961(9) 0.5873(2) 0.1065(7) 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(3) 0.0404(3) 0.0265(3) -0.00330(14) 0.00832(18) -0.00445(13) O1 0.0476(7) 0.0572(9) 0.0284(6) -0.0052(5) 0.0114(5) -0.0073(5) N1 0.0562(8) 0.0459(9) 0.0514(10) -0.0024(7) 0.0110(7) 0.0007(7) C1 0.0583(11) 0.0510(12) 0.0718(15) 0.0045(11) 0.0112(10) 0.0045(9) C2 0.0655(12) 0.0452(11) 0.0897(19) 0.0017(11) 0.0331(12) 0.0045(9) C3 0.0795(14) 0.0496(12) 0.0764(16) -0.0148(11) 0.0426(13) -0.0055(10) C4 0.0671(11) 0.0484(11) 0.0492(12) -0.0092(9) 0.0232(9) -0.0077(9) C5 0.0479(8) 0.0347(8) 0.0447(9) -0.0015(7) 0.0174(7) -0.0084(6) C6 0.0427(7) 0.0429(9) 0.0369(8) -0.0022(7) 0.0136(6) -0.0076(6) C7 0.0334(6) 0.0449(9) 0.0332(8) -0.0009(7) 0.0037(6) -0.0031(6) C8 0.0371(7) 0.0519(10) 0.0369(9) 0.0064(7) 0.0092(6) 0.0032(6) C9 0.0397(8) 0.0613(12) 0.0500(11) 0.0084(9) 0.0170(7) 0.0058(7) C10 0.0373(7) 0.0614(13) 0.0572(12) 0.0072(10) 0.0039(8) 0.0051(7) C11 0.0404(8) 0.0694(14) 0.0437(11) 0.0030(9) -0.0058(7) 0.0034(8) C12 0.0452(8) 0.0603(12) 0.0314(8) -0.0048(8) 0.0008(7) -0.0003(7) C13 0.0712(14) 0.113(2) 0.0675(17) 0.0282(16) 0.0403(13) 0.0456(16) F1 0.098(2) 0.151(4) 0.0568(19) -0.032(2) 0.0294(16) -0.013(3) F2 0.0780(19) 0.227(9) 0.086(3) 0.028(3) 0.0347(19) 0.101(4) F3 0.172(6) 0.098(3) 0.107(4) 0.032(3) 0.096(5) 0.013(4) F1A 0.104(6) 0.239(13) 0.056(3) 0.013(7) 0.034(4) 0.087(7) F2A 0.212(10) 0.222(11) 0.204(11) -0.032(9) 0.175(10) -0.069(9) F3A 0.269(16) 0.155(8) 0.125(8) 0.023(6) 0.134(10) 0.113(11) C14 0.0865(19) 0.151(4) 0.0552(17) 0.000(2) -0.0164(15) 0.047(2) F4 0.108(4) 0.188(9) 0.042(3) 0.045(5) 0.008(3) 0.054(4) F5 0.078(4) 0.294(12) 0.077(4) -0.004(6) -0.040(3) 0.007(6) F6 0.368(16) 0.114(6) 0.092(5) -0.008(5) -0.078(10) 0.131(9) F4A 0.069(3) 0.234(12) 0.100(7) 0.058(7) -0.006(3) 0.066(5) F5A 0.137(5) 0.210(10) 0.122(6) 0.117(8) -0.009(4) -0.023(5) F6A 0.229(14) 0.358(19) 0.081(6) -0.084(8) -0.084(7) 0.148(12) C15 0.0331(6) 0.0394(8) 0.0316(8) -0.0062(6) 0.0110(5) -0.0038(5) C16 0.0368(7) 0.0428(9) 0.0323(8) -0.0037(7) 0.0111(6) -0.0026(6) C17 0.0337(6) 0.0560(11) 0.0344(8) -0.0081(7) 0.0075(6) -0.0019(6) C18 0.0375(7) 0.0566(11) 0.0456(10) -0.0111(8) 0.0112(7) -0.0115(7) C19 0.0447(8) 0.0419(10) 0.0511(11) -0.0027(8) 0.0144(7) -0.0095(7) C20 0.0395(7) 0.0431(9) 0.0392(9) 0.0008(7) 0.0082(6) -0.0020(6) C21 0.0440(9) 0.0723(15) 0.0473(12) -0.0024(10) -0.0034(8) -0.0029(9) F7 0.0320(13) 0.197(9) 0.090(4) 0.065(5) -0.0003(17) -0.010(3) F8 0.146(6) 0.135(5) 0.038(2) -0.003(2) 0.023(3) 0.054(4) F9 0.108(3) 0.064(2) 0.085(4) 0.020(2) -0.036(3) -0.004(3) F7A 0.061(2) 0.237(11) 0.071(4) 0.089(6) 0.015(2) -0.007(4) F8A 0.133(5) 0.142(6) 0.089(4) -0.013(4) -0.036(4) 0.088(5) F9A 0.089(4) 0.162(7) 0.075(3) 0.017(4) -0.049(3) -0.054(4) C22 0.0705(12) 0.0474(12) 0.0664(15) 0.0005(10) 0.0136(11) -0.0184(10) F10 0.1098(12) 0.0668(11) 0.1075(14) 0.0344(9) -0.0027(10) -0.0235(9) F11 0.0824(10) 0.0905(13) 0.1537(19) 0.0382(13) 0.0502(11) -0.0198(9) F12 0.1559(17) 0.0554(9) 0.1115(15) -0.0138(9) 0.0392(13) -0.0349(10) _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 1.4874(14) . ? P1 C15 1.8070(15) . ? P1 C6 1.8077(18) . ? P1 C7 1.8178(17) . ? N1 C5 1.334(3) . ? N1 C1 1.344(3) . ? C1 C2 1.379(4) . ? C1 H1 0.9400 . ? C2 C3 1.347(4) . ? C2 H2 0.9400 . ? C3 C4 1.392(3) . ? C3 H3 0.9400 . ? C4 C5 1.387(3) . ? C4 H4 0.9400 . ? C5 C6 1.510(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.383(2) . ? C7 C12 1.389(2) . ? C8 C9 1.389(2) . ? C8 H8 0.9400 . ? C9 C10 1.376(3) . ? C9 C13 1.506(3) . ? C10 C11 1.384(3) . ? C10 H10 0.9400 . ? C11 C12 1.380(3) . ? C11 C14 1.507(4) . ? C12 H12 0.9400 . ? C13 F1A 1.152(7) . ? C13 F3A 1.221(12) . ? C13 F3 1.269(5) . ? C13 F2 1.279(5) . ? C13 F2A 1.432(10) . ? C13 F1 1.446(6) . ? C14 F4A 1.233(7) . ? C14 F4 1.263(8) . ? C14 F6 1.279(8) . ? C14 F6A 1.292(12) . ? C14 F5 1.356(9) . ? C14 F5A 1.387(10) . ? C15 C16 1.383(2) . ? C15 C20 1.390(2) . ? C16 C17 1.393(2) . ? C16 H16 0.9400 . ? C17 C18 1.372(3) . ? C17 C21 1.501(3) . ? C18 C19 1.382(3) . ? C18 H18 0.9400 . ? C19 C20 1.396(2) . ? C19 C22 1.484(3) . ? C20 H20 0.9400 . ? C21 F7A 1.224(6) . ? C21 F7 1.259(5) . ? C21 F8A 1.260(6) . ? C21 F8 1.333(7) . ? C21 F9A 1.352(7) . ? C21 F9 1.394(5) . ? C22 F11 1.315(3) . ? C22 F10 1.328(3) . ? C22 F12 1.334(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 O1 P1 C15 111.91(7) . . ? O1 P1 C6 114.72(8) . . ? C15 P1 C6 108.08(8) . . ? O1 P1 C7 109.15(8) . . ? C15 P1 C7 106.12(7) . . ? C6 P1 C7 106.37(8) . . ? C5 N1 C1 117.5(2) . . ? N1 C1 C2 123.4(2) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.4(2) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.38(18) . . ? N1 C5 C6 115.93(16) . . ? C4 C5 C6 121.69(18) . . ? C5 C6 P1 112.88(11) . . ? C5 C6 H6A 109.0 . . ? P1 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? P1 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C12 119.77(16) . . ? C8 C7 P1 123.78(13) . . ? C12 C7 P1 116.45(14) . . ? C7 C8 C9 119.10(17) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 121.49(19) . . ? C10 C9 C13 119.99(18) . . ? C8 C9 C13 118.50(19) . . ? C9 C10 C11 118.92(17) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C12 C11 C10 120.42(18) . . ? C12 C11 C14 119.3(2) . . ? C10 C11 C14 120.2(2) . . ? C11 C12 C7 120.25(18) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? F1A C13 F3A 120.7(9) . . ? F3 C13 F2 111.6(5) . . ? F1A C13 F2A 99.4(8) . . ? F3A C13 F2A 101.0(9) . . ? F3 C13 F1 98.7(4) . . ? F2 C13 F1 102.3(5) . . ? F1A C13 C9 117.1(3) . . ? F3A C13 C9 111.8(6) . . ? F3 C13 C9 115.4(3) . . ? F2 C13 C9 116.8(4) . . ? F2A C13 C9 102.2(5) . . ? F1 C13 C9 109.5(2) . . ? F4 C14 F6 113.5(9) . . ? F4A C14 F6A 108.9(7) . . ? F4 C14 F5 101.5(6) . . ? F6A C14 F5A 109.1(10) . . ? F4A C14 C11 115.0(5) . . ? F4 C14 C11 115.2(4) . . ? F6 C14 C11 113.3(4) . . ? F6A C14 C11 109.9(7) . . ? F5 C14 C11 108.4(6) . . ? F5A C14 C11 108.5(4) . . ? C16 C15 C20 120.52(15) . . ? C16 C15 P1 123.16(13) . . ? C20 C15 P1 116.24(13) . . ? C15 C16 C17 119.37(17) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 120.87(16) . . ? C18 C17 C21 120.41(16) . . ? C16 C17 C21 118.72(18) . . ? C17 C18 C19 119.49(15) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C18 C19 C20 120.78(17) . . ? C18 C19 C22 118.81(17) . . ? C20 C19 C22 120.40(19) . . ? C15 C20 C19 118.90(17) . . ? C15 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? F7A C21 F8A 115.7(7) . . ? F7 C21 F8 107.9(6) . . ? F7A C21 F9A 105.3(6) . . ? F8A C21 F9A 103.5(5) . . ? F7 C21 F9 105.4(5) . . ? F7A C21 C17 113.7(4) . . ? F7 C21 C17 117.7(4) . . ? F8A C21 C17 109.9(3) . . ? F8 C21 C17 112.7(4) . . ? F9A C21 C17 107.8(4) . . ? F9 C21 C17 113.6(2) . . ? F11 C22 F10 106.2(2) . . ? F11 C22 F12 107.4(2) . . ? F10 C22 F12 104.3(2) . . ? F11 C22 C19 112.9(2) . . ? F10 C22 C19 113.71(17) . . ? F12 C22 C19 111.8(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 C5 N1 C1 C2 -1.0(3) . . . . ? N1 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C1 N1 C5 C4 0.8(3) . . . . ? C1 N1 C5 C6 -179.13(17) . . . . ? C3 C4 C5 N1 0.4(3) . . . . ? C3 C4 C5 C6 -179.66(17) . . . . ? N1 C5 C6 P1 109.07(16) . . . . ? C4 C5 C6 P1 -70.86(19) . . . . ? O1 P1 C6 C5 53.98(15) . . . . ? C15 P1 C6 C5 -71.65(14) . . . . ? C7 P1 C6 C5 174.76(12) . . . . ? O1 P1 C7 C8 177.77(15) . . . . ? C15 P1 C7 C8 -61.46(17) . . . . ? C6 P1 C7 C8 53.48(17) . . . . ? O1 P1 C7 C12 -2.75(16) . . . . ? C15 P1 C7 C12 118.02(14) . . . . ? C6 P1 C7 C12 -127.04(15) . . . . ? C12 C7 C8 C9 1.9(3) . . . . ? P1 C7 C8 C9 -178.65(14) . . . . ? C7 C8 C9 C10 -0.8(3) . . . . ? C7 C8 C9 C13 -179.4(2) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C13 C9 C10 C11 177.5(2) . . . . ? C9 C10 C11 C12 1.9(3) . . . . ? C9 C10 C11 C14 -174.9(3) . . . . ? C10 C11 C12 C7 -0.8(3) . . . . ? C14 C11 C12 C7 176.0(3) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? P1 C7 C12 C11 179.38(16) . . . . ? C10 C9 C13 F1A -175.2(10) . . . . ? C8 C9 C13 F1A 3.5(11) . . . . ? C10 C9 C13 F3A -29.9(10) . . . . ? C8 C9 C13 F3A 148.8(9) . . . . ? C10 C9 C13 F3 132.2(5) . . . . ? C8 C9 C13 F3 -49.2(6) . . . . ? C10 C9 C13 F2 -2.0(7) . . . . ? C8 C9 C13 F2 176.7(6) . . . . ? C10 C9 C13 F2A 77.5(8) . . . . ? C8 C9 C13 F2A -103.9(7) . . . . ? C10 C9 C13 F1 -117.6(3) . . . . ? C8 C9 C13 F1 61.1(4) . . . . ? C12 C11 C14 F4A 165.6(9) . . . . ? C10 C11 C14 F4A -17.6(10) . . . . ? C12 C11 C14 F4 0.7(8) . . . . ? C10 C11 C14 F4 177.5(7) . . . . ? C12 C11 C14 F6 -132.5(12) . . . . ? C10 C11 C14 F6 44.3(13) . . . . ? C12 C11 C14 F6A 42.4(12) . . . . ? C10 C11 C14 F6A -140.8(11) . . . . ? C12 C11 C14 F5 113.6(7) . . . . ? C10 C11 C14 F5 -69.6(7) . . . . ? C12 C11 C14 F5A -76.8(8) . . . . ? C10 C11 C14 F5A 100.0(8) . . . . ? O1 P1 C15 C16 -125.55(14) . . . . ? C6 P1 C15 C16 1.71(15) . . . . ? C7 P1 C15 C16 115.48(14) . . . . ? O1 P1 C15 C20 51.33(15) . . . . ? C6 P1 C15 C20 178.60(12) . . . . ? C7 P1 C15 C20 -67.64(14) . . . . ? C20 C15 C16 C17 -0.5(2) . . . . ? P1 C15 C16 C17 176.21(12) . . . . ? C15 C16 C17 C18 1.5(3) . . . . ? C15 C16 C17 C21 -178.47(16) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C21 C17 C18 C19 179.69(18) . . . . ? C17 C18 C19 C20 -1.9(3) . . . . ? C17 C18 C19 C22 178.79(19) . . . . ? C16 C15 C20 C19 -1.5(3) . . . . ? P1 C15 C20 C19 -178.51(13) . . . . ? C18 C19 C20 C15 2.8(3) . . . . ? C22 C19 C20 C15 -177.92(18) . . . . ? C18 C17 C21 F7A 116.1(6) . . . . ? C16 C17 C21 F7A -63.9(6) . . . . ? C18 C17 C21 F7 -35.1(6) . . . . ? C16 C17 C21 F7 144.9(5) . . . . ? C18 C17 C21 F8A -112.4(6) . . . . ? C16 C17 C21 F8A 67.5(6) . . . . ? C18 C17 C21 F8 91.6(5) . . . . ? C16 C17 C21 F8 -88.5(5) . . . . ? C18 C17 C21 F9A -0.2(5) . . . . ? C16 C17 C21 F9A 179.7(4) . . . . ? C18 C17 C21 F9 -158.9(4) . . . . ? C16 C17 C21 F9 21.0(4) . . . . ? C18 C19 C22 F11 64.1(3) . . . . ? C20 C19 C22 F11 -115.2(2) . . . . ? C18 C19 C22 F10 -174.9(2) . . . . ? C20 C19 C22 F10 5.8(3) . . . . ? C18 C19 C22 F12 -57.1(3) . . . . ? C20 C19 C22 F12 123.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6A O1 0.98 2.45 3.364(2) 155.7 4_566 C8 H8 O1 0.94 2.26 3.188(2) 168.0 4_566 C12 H12 O1 0.94 2.48 2.930(2) 109.1 . C16 H16 F9 0.94 2.44 2.766(5) 100.1 . C16 H16 N1 0.94 2.42 3.193(3) 139.4 . C18 H18 F9A 0.94 2.27 2.611(7) 100.9 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.634 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.059 data_rpsl21 _database_code_depnum_ccdc_archive 'CCDC 715684' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 F6 N O P' _chemical_formula_sum 'C20 H14 F6 N O P' _chemical_formula_weight 429.29 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9554(4) _cell_length_b 9.6902(4) _cell_length_c 11.0339(4) _cell_angle_alpha 88.599(2) _cell_angle_beta 74.127(2) _cell_angle_gamma 88.578(2) _cell_volume 920.57(7) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6585 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 32.07 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; 0.5 degree phi and omega scans, 20s per frame, 20 hr data collection time, 5.5cm detector distance ; _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_% 0.0 _diffrn_reflns_number 19527 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 32.13 _reflns_number_total 6424 _reflns_number_gt 5154 _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[\s^2^(Fo^2^)+(0.0865P)^2^+0.3882P] 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_number_reflns 6424 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1459 _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 P P 0.76162(4) 0.24549(4) 0.38928(3) 0.03009(11) Uani 1 1 d . . . O O 0.66413(14) 0.36517(12) 0.37231(11) 0.0375(2) Uani 1 1 d . . . N N 0.68734(17) 0.19009(16) 0.74341(13) 0.0387(3) Uani 1 1 d . . . C1 C 0.6315(2) 0.2507(2) 0.85495(15) 0.0422(4) Uani 1 1 d . . . H1 H 0.6789 0.2280 0.9192 0.051 Uiso 1 1 calc R . . C2 C 0.5088(2) 0.34428(19) 0.88132(16) 0.0424(4) Uani 1 1 d . . . H2 H 0.4717 0.3819 0.9620 0.051 Uiso 1 1 calc R . . C3 C 0.4418(2) 0.38130(19) 0.78620(18) 0.0429(4) Uani 1 1 d . . . H3 H 0.3604 0.4472 0.7999 0.052 Uiso 1 1 calc R . . C4 C 0.49697(19) 0.31955(18) 0.67011(16) 0.0392(3) Uani 1 1 d . . . H4 H 0.4535 0.3431 0.6037 0.047 Uiso 1 1 calc R . . C5 C 0.61736(18) 0.22232(16) 0.65305(13) 0.0331(3) Uani 1 1 d . . . C6 C 0.6745(2) 0.14453(17) 0.53196(15) 0.0374(3) Uani 1 1 d . . . H6A H 0.5868 0.0948 0.5182 0.045 Uiso 1 1 calc R . . H6B H 0.7514 0.0752 0.5432 0.045 Uiso 1 1 calc R . . C7 C 0.6960(2) 0.07309(16) 0.20045(15) 0.0362(3) Uani 1 1 d . . . C8 C 0.7329(3) -0.03843(19) 0.11943(18) 0.0490(4) Uani 1 1 d . . . H8 H 0.6662 -0.0601 0.0703 0.059 Uiso 1 1 calc R . . C9 C 0.8651(3) -0.1172(2) 0.1102(2) 0.0561(5) Uani 1 1 d . . . H9 H 0.8875 -0.1926 0.0558 0.067 Uiso 1 1 calc R . . C10 C 0.9647(3) -0.0859(2) 0.1806(2) 0.0523(5) Uani 1 1 d . . . H10 H 1.0545 -0.1404 0.1752 0.063 Uiso 1 1 calc R . . C11 C 0.9317(2) 0.02644(18) 0.25945(18) 0.0428(4) Uani 1 1 d . . . H11 H 1.0014 0.0487 0.3057 0.051 Uiso 1 1 calc R . . C12 C 0.79621(19) 0.10822(15) 0.27201(14) 0.0339(3) Uani 1 1 d . . . C13 C 0.5466(2) 0.15055(19) 0.20868(18) 0.0428(4) Uani 1 1 d . . . F1 F 0.56659(15) 0.28082(12) 0.16647(12) 0.0505(3) Uani 1 1 d . . . F2 F 0.45573(14) 0.15416(14) 0.32814(12) 0.0559(3) Uani 1 1 d . . . F3 F 0.46227(18) 0.09290(15) 0.14054(15) 0.0658(4) Uani 1 1 d . . . C14 C 1.05219(18) 0.38135(15) 0.30383(14) 0.0333(3) Uani 1 1 d . . . C15 C 1.1899(2) 0.42663(18) 0.32270(19) 0.0432(4) Uani 1 1 d . . . H15 H 1.2552 0.4828 0.2608 0.052 Uiso 1 1 calc R . . C16 C 1.2329(2) 0.3907(2) 0.4306(2) 0.0462(4) Uani 1 1 d . . . H16 H 1.3254 0.4239 0.4428 0.055 Uiso 1 1 calc R . . C17 C 1.1391(2) 0.3059(2) 0.52025(17) 0.0442(4) Uani 1 1 d . . . H17 H 1.1686 0.2794 0.5931 0.053 Uiso 1 1 calc R . . C18 C 1.0006(2) 0.25940(19) 0.50289(15) 0.0388(3) Uani 1 1 d . . . H18 H 0.9374 0.2019 0.5648 0.047 Uiso 1 1 calc R . . C19 C 0.95340(18) 0.29619(15) 0.39546(13) 0.0315(3) Uani 1 1 d . . . C20 C 1.0183(2) 0.43184(18) 0.18398(16) 0.0403(3) Uani 1 1 d . . . F4 F 0.92376(16) 0.35345(13) 0.14334(10) 0.0531(3) Uani 1 1 d . . . F5 F 1.14699(18) 0.4413(2) 0.08932(14) 0.0872(6) Uani 1 1 d . . . F6 F 0.9527(2) 0.55710(14) 0.19577(16) 0.0784(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 P 0.03477(19) 0.03141(18) 0.02481(17) 0.00087(12) -0.00921(13) -0.00374(13) O 0.0407(6) 0.0359(5) 0.0367(6) -0.0001(4) -0.0124(4) 0.0017(4) N 0.0384(7) 0.0476(7) 0.0288(6) 0.0053(5) -0.0077(5) 0.0029(5) C1 0.0432(9) 0.0552(10) 0.0283(7) 0.0041(6) -0.0103(6) 0.0000(7) C2 0.0430(9) 0.0460(9) 0.0346(7) -0.0026(6) -0.0040(6) -0.0032(7) C3 0.0364(8) 0.0433(8) 0.0459(9) 0.0033(7) -0.0063(6) 0.0008(6) C4 0.0337(7) 0.0477(9) 0.0369(7) 0.0074(6) -0.0117(6) -0.0025(6) C5 0.0331(7) 0.0380(7) 0.0272(6) 0.0060(5) -0.0065(5) -0.0074(5) C6 0.0444(8) 0.0367(7) 0.0300(7) 0.0032(5) -0.0078(6) -0.0095(6) C7 0.0455(8) 0.0319(7) 0.0317(7) -0.0002(5) -0.0108(6) -0.0047(6) C8 0.0693(12) 0.0379(8) 0.0409(9) -0.0088(7) -0.0156(8) -0.0073(8) C9 0.0759(14) 0.0388(9) 0.0488(10) -0.0143(8) -0.0080(9) 0.0035(9) C10 0.0601(12) 0.0397(9) 0.0517(10) -0.0061(8) -0.0067(9) 0.0094(8) C11 0.0482(9) 0.0384(8) 0.0435(8) -0.0012(6) -0.0155(7) 0.0033(7) C12 0.0409(8) 0.0301(6) 0.0303(6) 0.0001(5) -0.0087(5) -0.0021(5) C13 0.0473(9) 0.0408(8) 0.0436(9) 0.0002(6) -0.0178(7) -0.0046(7) F1 0.0650(7) 0.0417(5) 0.0530(6) 0.0040(5) -0.0305(6) 0.0001(5) F2 0.0439(6) 0.0641(7) 0.0552(7) 0.0020(6) -0.0067(5) 0.0013(5) F3 0.0693(9) 0.0633(8) 0.0809(10) -0.0100(7) -0.0463(8) -0.0084(6) C14 0.0368(7) 0.0311(6) 0.0320(6) -0.0011(5) -0.0089(5) -0.0025(5) C15 0.0404(8) 0.0403(8) 0.0498(9) 0.0061(7) -0.0136(7) -0.0104(6) C16 0.0412(9) 0.0472(9) 0.0554(10) -0.0021(8) -0.0214(8) -0.0067(7) C17 0.0422(9) 0.0558(10) 0.0387(8) -0.0025(7) -0.0178(7) 0.0000(7) C18 0.0382(8) 0.0495(9) 0.0298(7) 0.0018(6) -0.0111(6) -0.0036(6) C19 0.0352(7) 0.0338(6) 0.0257(6) -0.0027(5) -0.0087(5) -0.0024(5) C20 0.0462(9) 0.0401(8) 0.0341(7) 0.0066(6) -0.0101(6) -0.0085(6) F4 0.0714(8) 0.0581(7) 0.0356(5) 0.0095(5) -0.0235(5) -0.0220(6) F5 0.0571(8) 0.1554(17) 0.0422(7) 0.0283(9) -0.0023(6) -0.0242(10) F6 0.1395(15) 0.0409(6) 0.0710(9) 0.0030(6) -0.0577(10) 0.0128(8) _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 P O 1.4734(12) . ? P C19 1.8175(15) . ? P C6 1.8262(15) . ? P C12 1.8396(15) . ? N C1 1.339(2) . ? N C5 1.342(2) . ? C1 C2 1.380(3) . ? C1 H1 0.9400 . ? C2 C3 1.380(3) . ? C2 H2 0.9400 . ? C3 C4 1.385(3) . ? C3 H3 0.9400 . ? C4 C5 1.390(2) . ? C4 H4 0.9400 . ? C5 C6 1.507(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.394(2) . ? C7 C12 1.401(2) . ? C7 C13 1.499(3) . ? C8 C9 1.374(3) . ? C8 H8 0.9400 . ? C9 C10 1.377(3) . ? C9 H9 0.9400 . ? C10 C11 1.385(3) . ? C10 H10 0.9400 . ? C11 C12 1.409(2) . ? C11 H11 0.9400 . ? C13 F1 1.334(2) . ? C13 F3 1.341(2) . ? C13 F2 1.347(2) . ? C14 C15 1.389(2) . ? C14 C19 1.411(2) . ? C14 C20 1.504(2) . ? C15 C16 1.383(3) . ? C15 H15 0.9400 . ? C16 C17 1.378(3) . ? C16 H16 0.9400 . ? C17 C18 1.393(2) . ? C17 H17 0.9400 . ? C18 C19 1.399(2) . ? C18 H18 0.9400 . ? C20 F4 1.323(2) . ? C20 F6 1.329(2) . ? C20 F5 1.331(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O P C19 112.11(7) . . ? O P C6 112.66(8) . . ? C19 P C6 107.93(7) . . ? O P C12 117.96(7) . . ? C19 P C12 105.31(7) . . ? C6 P C12 99.77(7) . . ? C1 N C5 117.25(15) . . ? N C1 C2 124.04(16) . . ? N C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 118.30(16) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 118.73(16) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 119.18(15) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N C5 C4 122.39(15) . . ? N C5 C6 116.08(14) . . ? C4 C5 C6 121.52(14) . . ? C5 C6 P 117.13(11) . . ? C5 C6 H6A 108.0 . . ? P C6 H6A 108.0 . . ? C5 C6 H6B 108.0 . . ? P C6 H6B 108.0 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C12 119.94(17) . . ? C8 C7 C13 117.83(16) . . ? C12 C7 C13 122.22(14) . . ? C9 C8 C7 121.12(19) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 120.11(17) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.56(19) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 121.65(18) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C7 C12 C11 117.60(14) . . ? C7 C12 P 125.90(12) . . ? C11 C12 P 116.38(12) . . ? F1 C13 F3 105.36(15) . . ? F1 C13 F2 107.23(15) . . ? F3 C13 F2 106.37(16) . . ? F1 C13 C7 113.45(15) . . ? F3 C13 C7 112.45(15) . . ? F2 C13 C7 111.49(15) . . ? C15 C14 C19 120.01(15) . . ? C15 C14 C20 115.50(14) . . ? C19 C14 C20 124.48(14) . . ? C16 C15 C14 121.34(16) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 119.48(16) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 119.97(16) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C19 121.59(16) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? C18 C19 C14 117.60(14) . . ? C18 C19 P 118.17(11) . . ? C14 C19 P 123.96(11) . . ? F4 C20 F6 105.56(16) . . ? F4 C20 F5 105.89(16) . . ? F6 C20 F5 106.10(17) . . ? F4 C20 C14 114.87(13) . . ? F6 C20 C14 111.98(15) . . ? F5 C20 C14 111.81(16) . . ? 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 C5 N C1 C2 -0.7(3) . . . . ? N C1 C2 C3 -2.0(3) . . . . ? C1 C2 C3 C4 2.2(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C1 N C5 C4 3.3(2) . . . . ? C1 N C5 C6 -175.47(15) . . . . ? C3 C4 C5 N -3.0(2) . . . . ? C3 C4 C5 C6 175.65(15) . . . . ? N C5 C6 P -117.58(14) . . . . ? C4 C5 C6 P 63.67(19) . . . . ? O P C6 C5 -50.03(15) . . . . ? C19 P C6 C5 74.29(14) . . . . ? C12 P C6 C5 -176.00(13) . . . . ? C12 C7 C8 C9 1.4(3) . . . . ? C13 C7 C8 C9 -177.71(18) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 1.6(3) . . . . ? C8 C7 C12 C11 -0.7(2) . . . . ? C13 C7 C12 C11 178.41(16) . . . . ? C8 C7 C12 P -176.58(13) . . . . ? C13 C7 C12 P 2.5(2) . . . . ? C10 C11 C12 C7 -0.8(3) . . . . ? C10 C11 C12 P 175.49(15) . . . . ? O P C12 C7 -28.36(17) . . . . ? C19 P C12 C7 -154.31(14) . . . . ? C6 P C12 C7 93.91(15) . . . . ? O P C12 C11 155.72(13) . . . . ? C19 P C12 C11 29.77(14) . . . . ? C6 P C12 C11 -82.02(14) . . . . ? C8 C7 C13 F1 -115.04(18) . . . . ? C12 C7 C13 F1 65.8(2) . . . . ? C8 C7 C13 F3 4.4(2) . . . . ? C12 C7 C13 F3 -174.73(15) . . . . ? C8 C7 C13 F2 123.77(17) . . . . ? C12 C7 C13 F2 -55.4(2) . . . . ? C19 C14 C15 C16 -0.4(3) . . . . ? C20 C14 C15 C16 178.29(17) . . . . ? C14 C15 C16 C17 1.4(3) . . . . ? C15 C16 C17 C18 -1.3(3) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C17 C18 C19 C14 0.7(2) . . . . ? C17 C18 C19 P -173.59(14) . . . . ? C15 C14 C19 C18 -0.6(2) . . . . ? C20 C14 C19 C18 -179.21(15) . . . . ? C15 C14 C19 P 173.29(13) . . . . ? C20 C14 C19 P -5.3(2) . . . . ? O P C19 C18 121.83(13) . . . . ? C6 P C19 C18 -2.81(15) . . . . ? C12 P C19 C18 -108.69(13) . . . . ? O P C19 C14 -52.06(15) . . . . ? C6 P C19 C14 -176.71(13) . . . . ? C12 P C19 C14 77.42(14) . . . . ? C15 C14 C20 F4 156.35(16) . . . . ? C19 C14 C20 F4 -25.0(2) . . . . ? C15 C14 C20 F6 -83.3(2) . . . . ? C19 C14 C20 F6 95.4(2) . . . . ? C15 C14 C20 F5 35.7(2) . . . . ? C19 C14 C20 F5 -145.71(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8 F3 0.94 2.30 2.664(3) 102.5 . C18 H18 N 0.94 2.55 3.362(2) 144.8 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 32.13 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.785 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.065 data_rpsl22 _database_code_depnum_ccdc_archive 'CCDC 715685' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F12 N O2 P' _chemical_formula_sum 'C22 H12 F12 N O2 P' _chemical_formula_weight 581.30 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 18.7789(6) _cell_length_b 24.0769(8) _cell_length_c 11.4618(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.727(2) _cell_angle_gamma 90.00 _cell_volume 4587.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7432 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.32 _exptl_crystal_description block-cutfromplate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.926 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details Bruker,SADABS _exptl_special_details ; 0.5 deg phi and omega scans,20s per frame, 19 h data collection, 5.5 cm detector distance ; _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 38656 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5720 _reflns_number_gt 4773 _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. disorder on CF3's each F occupies 2 positions whose occupancies total to 100% eg occupancy F1+ occupancy F1A0% C21 F7,F8,F9/F7A,F8A,F9A 51%/49% C22 F10,F11,F12/F10A,F11A,F12A 63%/37% ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w[\s^2^(Fo^2^)+(0.0625P)^2^+5.9206P] 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_number_reflns 5720 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1265 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 P P 0.15284(3) 0.013016(17) 0.10606(4) 0.02632(12) Uani 1 1 d . . . N N 0.14571(9) 0.12851(6) -0.06807(15) 0.0352(3) Uani 1 1 d . . . O1 O 0.20993(8) 0.10386(6) -0.05878(15) 0.0439(3) Uani 1 1 d . . . O2 O 0.10140(8) -0.01678(5) 0.15196(12) 0.0346(3) Uani 1 1 d . . . C1 C 0.14199(14) 0.18488(9) -0.0679(2) 0.0478(5) Uani 1 1 d . . . H1A H 0.1854 0.2058 -0.0636 0.057 Uiso 1 1 calc R . . C2 C 0.07629(16) 0.21151(9) -0.0738(2) 0.0546(6) Uani 1 1 d . . . H2 H 0.0749 0.2505 -0.0727 0.065 Uiso 1 1 calc R . . C3 C 0.01185(15) 0.18118(9) -0.0814(2) 0.0499(5) Uani 1 1 d . . . H3 H -0.0338 0.1992 -0.0858 0.060 Uiso 1 1 calc R . . C4 C 0.01571(12) 0.12394(8) -0.08221(19) 0.0385(4) Uani 1 1 d . . . H4 H -0.0279 0.1027 -0.0882 0.046 Uiso 1 1 calc R . . C5 C 0.08314(10) 0.09764(7) -0.07433(15) 0.0302(3) Uani 1 1 d . . . C6 C 0.09520(10) 0.03640(7) -0.06500(15) 0.0300(3) Uani 1 1 d . . . H6A H 0.1236 0.0255 -0.1146 0.036 Uiso 1 1 calc R . . H6B H 0.0426 0.0180 -0.1053 0.036 Uiso 1 1 calc R . . C7 C 0.19563(10) 0.07442(7) 0.20669(15) 0.0294(3) Uani 1 1 d . . . C8 C 0.15197(11) 0.09708(7) 0.26500(16) 0.0332(4) Uani 1 1 d . . . H8 H 0.1039 0.0801 0.2528 0.040 Uiso 1 1 calc R . . C9 C 0.17912(13) 0.14465(8) 0.34123(18) 0.0404(4) Uani 1 1 d . . . C10 C 0.24978(14) 0.16991(8) 0.3605(2) 0.0464(5) Uani 1 1 d . . . H10 H 0.2679 0.2023 0.4118 0.056 Uiso 1 1 calc R . . C11 C 0.29352(13) 0.14692(8) 0.3034(2) 0.0429(4) Uani 1 1 d . . . C12 C 0.26708(11) 0.09929(8) 0.22699(17) 0.0350(4) Uani 1 1 d . . . H12 H 0.2975 0.0839 0.1891 0.042 Uiso 1 1 calc R . . C13 C 0.13027(16) 0.16978(10) 0.4007(2) 0.0559(6) Uani 1 1 d . . . F1 F 0.08564(14) 0.21044(9) 0.3312(2) 0.1043(7) Uani 1 1 d . . . F2 F 0.17570(13) 0.19059(10) 0.51919(19) 0.1114(8) Uani 1 1 d . . . F3 F 0.08300(17) 0.13417(9) 0.4151(3) 0.1171(9) Uani 1 1 d . . . C14 C 0.36896(17) 0.17509(11) 0.3219(3) 0.0657(7) Uani 1 1 d . . . F4 F 0.41483(14) 0.14422(10) 0.2925(3) 0.1290(10) Uani 1 1 d . . . F5 F 0.41485(12) 0.19095(11) 0.4450(2) 0.1150(8) Uani 1 1 d . . . F6 F 0.35444(15) 0.22070(11) 0.2554(3) 0.1511(13) Uani 1 1 d . . . C15 C 0.23709(10) -0.02833(7) 0.12199(16) 0.0299(3) Uani 1 1 d . . . C16 C 0.28544(11) -0.01248(8) 0.06539(17) 0.0329(4) Uani 1 1 d . . . H16 H 0.2719 0.0188 0.0102 0.039 Uiso 1 1 calc R . . C17 C 0.35355(11) -0.04313(8) 0.09091(18) 0.0370(4) Uani 1 1 d . A . C18 C 0.37264(12) -0.09017(9) 0.1689(2) 0.0414(4) Uani 1 1 d . . . H18 H 0.4185 -0.1111 0.1848 0.050 Uiso 1 1 calc R . . C19 C 0.32391(12) -0.10614(8) 0.2233(2) 0.0405(4) Uani 1 1 d . B . C20 C 0.25660(11) -0.07524(7) 0.20224(18) 0.0348(4) Uani 1 1 d . . . H20 H 0.2245 -0.0858 0.2416 0.042 Uiso 1 1 calc R . . C21 C 0.40927(13) -0.02249(11) 0.0405(2) 0.0486(5) Uani 1 1 d . . . F7 F 0.3731(6) -0.0034(5) -0.0780(10) 0.071(3) Uani 0.51 1 d P A 1 F8 F 0.4497(4) -0.0687(3) 0.0236(7) 0.0834(18) Uani 0.51 1 d P A 1 F9 F 0.4614(4) 0.0089(3) 0.1154(6) 0.081(2) Uani 0.51 1 d P A 1 F7A F 0.4743(3) -0.0489(3) 0.0769(6) 0.084(2) Uani 0.49 1 d P A 2 F8A F 0.4368(5) 0.0319(3) 0.0920(9) 0.087(2) Uani 0.49 1 d P A 2 F9A F 0.3731(7) -0.0116(6) -0.0851(10) 0.072(3) Uani 0.49 1 d P A 2 C22 C 0.34667(17) -0.15630(10) 0.3123(3) 0.0602(6) Uani 1 1 d . . . F10 F 0.2877(3) -0.1890(3) 0.2918(6) 0.095(2) Uani 0.63 1 d P B 1 F11 F 0.4080(3) -0.1839(2) 0.3177(5) 0.0934(16) Uani 0.63 1 d P B 1 F12 F 0.3732(4) -0.1412(3) 0.4392(5) 0.0807(15) Uani 0.63 1 d P B 1 F10A F 0.3990(8) -0.1499(5) 0.4216(13) 0.178(8) Uani 0.37 1 d P B 2 F11A F 0.2816(7) -0.1811(5) 0.3062(12) 0.082(3) Uani 0.37 1 d P B 2 F12A F 0.3610(7) -0.1992(3) 0.2401(10) 0.121(3) Uani 0.37 1 d P B 2 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 P 0.0278(2) 0.0267(2) 0.0276(2) -0.00163(15) 0.01557(17) -0.00289(15) N 0.0373(8) 0.0375(8) 0.0333(7) 0.0041(6) 0.0186(6) -0.0017(6) O1 0.0371(7) 0.0498(8) 0.0516(8) 0.0040(6) 0.0263(6) -0.0011(6) O2 0.0353(7) 0.0358(6) 0.0385(6) 0.0017(5) 0.0221(6) -0.0046(5) C1 0.0547(12) 0.0378(10) 0.0530(12) 0.0058(9) 0.0268(10) -0.0084(9) C2 0.0736(16) 0.0307(10) 0.0627(14) 0.0064(9) 0.0345(12) 0.0038(10) C3 0.0577(13) 0.0415(11) 0.0587(13) 0.0094(9) 0.0341(11) 0.0146(10) C4 0.0384(10) 0.0420(10) 0.0393(9) 0.0057(8) 0.0215(8) 0.0036(8) C5 0.0339(8) 0.0330(8) 0.0248(7) 0.0017(6) 0.0146(7) -0.0009(7) C6 0.0315(8) 0.0322(8) 0.0271(7) -0.0028(6) 0.0144(6) -0.0027(7) C7 0.0334(8) 0.0283(8) 0.0259(7) -0.0001(6) 0.0133(6) -0.0020(6) C8 0.0370(9) 0.0327(8) 0.0306(8) -0.0003(6) 0.0163(7) 0.0005(7) C9 0.0518(11) 0.0350(9) 0.0346(9) -0.0032(7) 0.0202(8) 0.0050(8) C10 0.0567(13) 0.0329(9) 0.0435(10) -0.0097(8) 0.0182(9) -0.0052(9) C11 0.0462(11) 0.0363(10) 0.0421(10) -0.0034(8) 0.0171(9) -0.0107(8) C12 0.0370(9) 0.0351(9) 0.0339(8) -0.0019(7) 0.0174(7) -0.0055(7) C13 0.0667(15) 0.0499(12) 0.0542(13) -0.0120(10) 0.0308(12) 0.0100(11) F1 0.1137(16) 0.1030(15) 0.1159(16) 0.0301(12) 0.0701(14) 0.0642(13) F2 0.1081(15) 0.1447(19) 0.0731(11) -0.0546(12) 0.0353(11) 0.0279(14) F3 0.178(2) 0.0823(12) 0.180(2) -0.0360(14) 0.159(2) -0.0208(14) C14 0.0633(16) 0.0550(14) 0.0814(18) -0.0170(13) 0.0359(14) -0.0273(12) F4 0.0930(14) 0.1231(18) 0.212(3) -0.0797(18) 0.1055(18) -0.0670(13) F5 0.0776(13) 0.142(2) 0.1051(15) -0.0447(14) 0.0251(11) -0.0611(13) F6 0.1040(17) 0.1227(19) 0.201(3) 0.078(2) 0.0498(18) -0.0425(15) C15 0.0294(8) 0.0297(8) 0.0307(8) -0.0036(6) 0.0141(7) -0.0015(6) C16 0.0320(9) 0.0359(9) 0.0318(8) -0.0007(7) 0.0157(7) -0.0013(7) C17 0.0311(9) 0.0464(10) 0.0346(9) -0.0016(7) 0.0163(7) 0.0008(8) C18 0.0348(9) 0.0455(10) 0.0431(10) 0.0004(8) 0.0175(8) 0.0072(8) C19 0.0419(10) 0.0355(9) 0.0434(10) 0.0025(8) 0.0192(8) 0.0051(8) C20 0.0382(9) 0.0308(8) 0.0380(9) -0.0006(7) 0.0199(8) -0.0016(7) C21 0.0336(10) 0.0705(15) 0.0447(11) 0.0044(10) 0.0207(9) 0.0048(10) F7 0.046(4) 0.110(5) 0.066(5) 0.044(4) 0.034(4) 0.021(4) F8 0.082(4) 0.081(3) 0.128(5) 0.010(3) 0.083(4) 0.021(3) F9 0.061(3) 0.126(6) 0.058(2) -0.028(3) 0.031(2) -0.056(4) F7A 0.047(3) 0.118(6) 0.104(4) 0.055(4) 0.051(3) 0.036(3) F8A 0.089(5) 0.081(4) 0.120(5) -0.027(3) 0.074(4) -0.042(3) F9A 0.061(5) 0.120(6) 0.035(3) -0.005(3) 0.021(3) -0.036(4) C22 0.0617(15) 0.0453(13) 0.0781(17) 0.0201(12) 0.0364(14) 0.0174(11) F10 0.089(3) 0.054(3) 0.099(3) 0.026(2) 0.007(3) -0.019(2) F11 0.112(3) 0.080(3) 0.116(4) 0.053(3) 0.078(3) 0.066(3) F12 0.102(4) 0.084(2) 0.0496(19) 0.0270(17) 0.030(3) 0.026(2) F10A 0.115(10) 0.115(10) 0.149(12) 0.089(9) -0.068(7) -0.040(7) F11A 0.125(7) 0.055(4) 0.123(6) 0.041(4) 0.105(6) 0.033(4) F12A 0.202(10) 0.050(3) 0.176(9) 0.039(5) 0.143(8) 0.063(5) _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 P O2 1.4825(12) . ? P C15 1.8052(17) . ? P C7 1.8165(17) . ? P C6 1.8325(17) . ? N O1 1.303(2) . ? N C1 1.359(3) . ? N C5 1.364(2) . ? C1 C2 1.364(3) . ? C1 H1A 0.9400 . ? C2 C3 1.381(3) . ? C2 H2 0.9400 . ? C3 C4 1.380(3) . ? C3 H3 0.9400 . ? C4 C5 1.381(3) . ? C4 H4 0.9400 . ? C5 C6 1.488(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C12 1.387(2) . ? C7 C8 1.388(2) . ? C8 C9 1.386(3) . ? C8 H8 0.9400 . ? C9 C10 1.381(3) . ? C9 C13 1.501(3) . ? C10 C11 1.382(3) . ? C10 H10 0.9400 . ? C11 C12 1.387(3) . ? C11 C14 1.494(3) . ? C12 H12 0.9400 . ? C13 F1 1.294(3) . ? C13 F3 1.299(3) . ? C13 F2 1.321(3) . ? C14 F6 1.291(4) . ? C14 F4 1.295(3) . ? C14 F5 1.323(3) . ? C15 C16 1.392(2) . ? C15 C20 1.394(2) . ? C16 C17 1.385(3) . ? C16 H16 0.9400 . ? C17 C18 1.383(3) . ? C17 C21 1.496(3) . ? C18 C19 1.380(3) . ? C18 H18 0.9400 . ? C19 C20 1.388(3) . ? C19 C22 1.508(3) . ? C20 H20 0.9400 . ? C21 F9 1.219(6) . ? C21 F7A 1.264(6) . ? C21 F7 1.287(10) . ? C21 F9A 1.300(11) . ? C21 F8 1.410(7) . ? C21 F8A 1.430(8) . ? C22 F10A 1.189(12) . ? C22 F10 1.288(6) . ? C22 F11 1.305(5) . ? C22 F11A 1.332(11) . ? C22 F12 1.350(6) . ? C22 F12A 1.424(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 O2 P C15 112.48(8) . . ? O2 P C7 109.71(7) . . ? C15 P C7 106.07(8) . . ? O2 P C6 111.74(8) . . ? C15 P C6 109.35(8) . . ? C7 P C6 107.21(8) . . ? O1 N C1 120.08(17) . . ? O1 N C5 119.86(15) . . ? C1 N C5 120.04(17) . . ? N C1 C2 121.0(2) . . ? N C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 118.8(2) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.46(19) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N C5 C4 119.68(16) . . ? N C5 C6 115.96(15) . . ? C4 C5 C6 124.29(16) . . ? C5 C6 P 112.07(11) . . ? C5 C6 H6A 109.2 . . ? P C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? P C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C12 C7 C8 119.46(16) . . ? C12 C7 P 124.44(13) . . ? C8 C7 P 116.10(13) . . ? C9 C8 C7 120.13(17) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.61(18) . . ? C10 C9 C13 119.63(19) . . ? C8 C9 C13 119.74(19) . . ? C9 C10 C11 119.11(18) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C12 120.87(19) . . ? C10 C11 C14 118.96(19) . . ? C12 C11 C14 120.1(2) . . ? C7 C12 C11 119.80(18) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? F1 C13 F3 107.0(3) . . ? F1 C13 F2 105.6(2) . . ? F3 C13 F2 105.8(2) . . ? F1 C13 C9 112.6(2) . . ? F3 C13 C9 112.94(19) . . ? F2 C13 C9 112.4(2) . . ? F6 C14 F4 108.6(3) . . ? F6 C14 F5 103.8(3) . . ? F4 C14 F5 105.1(3) . . ? F6 C14 C11 112.1(3) . . ? F4 C14 C11 113.8(2) . . ? F5 C14 C11 112.7(2) . . ? C16 C15 C20 120.10(16) . . ? C16 C15 P 122.17(13) . . ? C20 C15 P 117.55(13) . . ? C17 C16 C15 119.59(17) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.59(17) . . ? C18 C17 C21 120.29(18) . . ? C16 C17 C21 118.98(18) . . ? C19 C18 C17 119.57(18) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 120.90(18) . . ? C18 C19 C22 119.30(19) . . ? C20 C19 C22 119.73(19) . . ? C19 C20 C15 119.21(17) . . ? C19 C20 H20 120.4 . . ? C15 C20 H20 120.4 . . ? F9 C21 F7 112.3(7) . . ? F7A C21 F7 118.9(6) . . ? F9 C21 F9A 119.3(7) . . ? F7A C21 F9A 113.2(7) . . ? F9 C21 F8 106.1(4) . . ? F7 C21 F8 101.0(6) . . ? F7A C21 F8A 102.5(4) . . ? F9A C21 F8A 100.0(7) . . ? F9 C21 C17 114.3(4) . . ? F7A C21 C17 116.6(3) . . ? F7 C21 C17 113.9(5) . . ? F9A C21 C17 113.3(6) . . ? F8 C21 C17 108.0(3) . . ? F8A C21 C17 109.1(4) . . ? F10 C22 F11 111.3(5) . . ? F10A C22 F11A 113.7(9) . . ? F10 C22 F12 102.5(5) . . ? F11 C22 F12 102.2(4) . . ? F10A C22 F12A 114.9(9) . . ? F11A C22 F12A 93.5(6) . . ? F10A C22 C19 116.3(6) . . ? F10 C22 C19 114.6(4) . . ? F11 C22 C19 113.9(3) . . ? F11A C22 C19 111.0(5) . . ? F12 C22 C19 111.0(3) . . ? F12A C22 C19 105.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N C1 C2 -178.15(19) . . . . ? C5 N C1 C2 0.1(3) . . . . ? N C1 C2 C3 -0.6(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? O1 N C5 C4 179.05(15) . . . . ? C1 N C5 C4 0.8(3) . . . . ? O1 N C5 C6 2.1(2) . . . . ? C1 N C5 C6 -176.09(17) . . . . ? C3 C4 C5 N -1.2(3) . . . . ? C3 C4 C5 C6 175.48(18) . . . . ? N C5 C6 P 81.79(16) . . . . ? C4 C5 C6 P -94.98(18) . . . . ? O2 P C6 C5 107.82(13) . . . . ? C15 P C6 C5 -126.99(12) . . . . ? C7 P C6 C5 -12.42(14) . . . . ? O2 P C7 C12 154.06(15) . . . . ? C15 P C7 C12 32.34(17) . . . . ? C6 P C7 C12 -84.42(16) . . . . ? O2 P C7 C8 -26.37(15) . . . . ? C15 P C7 C8 -148.09(13) . . . . ? C6 P C7 C8 95.15(14) . . . . ? C12 C7 C8 C9 1.0(3) . . . . ? P C7 C8 C9 -178.64(14) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C7 C8 C9 C13 178.24(18) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C13 C9 C10 C11 -178.9(2) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C9 C10 C11 C14 178.6(2) . . . . ? C8 C7 C12 C11 -1.0(3) . . . . ? P C7 C12 C11 178.52(14) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C14 C11 C12 C7 -177.9(2) . . . . ? C10 C9 C13 F1 81.0(3) . . . . ? C8 C9 C13 F1 -97.5(3) . . . . ? C10 C9 C13 F3 -157.7(2) . . . . ? C8 C9 C13 F3 23.8(3) . . . . ? C10 C9 C13 F2 -38.1(3) . . . . ? C8 C9 C13 F2 143.4(2) . . . . ? C10 C11 C14 F6 -71.9(3) . . . . ? C12 C11 C14 F6 106.4(3) . . . . ? C10 C11 C14 F4 164.4(3) . . . . ? C12 C11 C14 F4 -17.3(4) . . . . ? C10 C11 C14 F5 44.8(3) . . . . ? C12 C11 C14 F5 -136.9(2) . . . . ? O2 P C15 C16 169.17(13) . . . . ? C7 P C15 C16 -70.89(15) . . . . ? C6 P C15 C16 44.42(16) . . . . ? O2 P C15 C20 -15.69(16) . . . . ? C7 P C15 C20 104.25(14) . . . . ? C6 P C15 C20 -140.45(13) . . . . ? C20 C15 C16 C17 -0.9(3) . . . . ? P C15 C16 C17 174.09(14) . . . . ? C15 C16 C17 C18 1.9(3) . . . . ? C15 C16 C17 C21 -174.02(17) . . . . ? C16 C17 C18 C19 -1.0(3) . . . . ? C21 C17 C18 C19 174.84(19) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C17 C18 C19 C22 -177.8(2) . . . . ? C18 C19 C20 C15 1.8(3) . . . . ? C22 C19 C20 C15 178.7(2) . . . . ? C16 C15 C20 C19 -0.9(3) . . . . ? P C15 C20 C19 -176.10(14) . . . . ? C18 C17 C21 F9 -87.3(4) . . . . ? C16 C17 C21 F9 88.6(4) . . . . ? C18 C17 C21 F7A -2.5(5) . . . . ? C16 C17 C21 F7A 173.4(4) . . . . ? C18 C17 C21 F7 141.8(6) . . . . ? C16 C17 C21 F7 -42.3(7) . . . . ? C18 C17 C21 F9A 131.6(7) . . . . ? C16 C17 C21 F9A -52.5(7) . . . . ? C18 C17 C21 F8 30.5(4) . . . . ? C16 C17 C21 F8 -153.6(3) . . . . ? C18 C17 C21 F8A -117.9(4) . . . . ? C16 C17 C21 F8A 58.0(4) . . . . ? C18 C19 C22 F10A 77.2(11) . . . . ? C20 C19 C22 F10A -99.8(11) . . . . ? C18 C19 C22 F10 -136.9(4) . . . . ? C20 C19 C22 F10 46.1(5) . . . . ? C18 C19 C22 F11 -7.1(5) . . . . ? C20 C19 C22 F11 175.9(4) . . . . ? C18 C19 C22 F11A -150.7(5) . . . . ? C20 C19 C22 F11A 32.2(6) . . . . ? C18 C19 C22 F12 107.6(4) . . . . ? C20 C19 C22 F12 -69.4(4) . . . . ? C18 C19 C22 F12A -50.9(6) . . . . ? C20 C19 C22 F12A 132.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 O2 0.94 2.40 3.240(2) 147.9 5 C6 H6A O2 0.98 2.52 3.334(2) 140.7 6 C6 H6B O2 0.98 2.50 3.380(2) 149.1 5 C8 H8 O2 0.94 2.59 2.992(2) 105.9 . C12 H12 O1 0.94 2.58 2.936(2) 102.8 . C16 H16 O1 0.94 2.31 3.163(2) 151.4 . C20 H20 O1 0.94 2.47 3.314(2) 149.9 6_556 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.578 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.053 data_rpsl32 _database_code_depnum_ccdc_archive 'CCDC 715686' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 F6 N O2 P' _chemical_formula_sum 'C20 H14 F6 N O2 P' _chemical_formula_weight 445.29 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8219(6) _cell_length_b 8.8196(7) _cell_length_c 14.4992(12) _cell_angle_alpha 84.198(4) _cell_angle_beta 81.657(4) _cell_angle_gamma 72.516(4) _cell_volume 942.18(13) _cell_formula_units_Z 2 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used 9858 _cell_measurement_theta_min 5.47 _cell_measurement_theta_max 65.73 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details Bruker,SADABS _exptl_special_details ; 0.5 deg wide phi and omega scans, 15s/frame exposure 19 h data collection, 5.0cm detector distance ; _diffrn_ambient_temperature 225(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 25744 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 33.07 _reflns_number_total 7013 _reflns_number_gt 5849 _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[\s^2^(Fo^2^)+(0.0573P)^2^+0.4033P] 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_number_reflns 7013 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.17704(4) 0.65694(3) 0.20684(2) 0.02238(8) Uani 1 1 d . . . O1 O 0.67512(13) 0.62155(13) 0.05306(7) 0.0340(2) Uani 1 1 d . . . O2 O 0.01323(13) 0.78981(11) 0.19093(7) 0.0317(2) Uani 1 1 d . . . N1 N 0.54928(15) 0.72501(13) 0.01041(7) 0.0261(2) Uani 1 1 d . . . C1 C 0.5987(2) 0.82273(17) -0.06018(9) 0.0336(3) Uani 1 1 d . . . H1A H 0.7217 0.8145 -0.0770 0.040 Uiso 1 1 calc R . . C2 C 0.4718(2) 0.93317(17) -0.10718(10) 0.0396(3) Uani 1 1 d . . . H2 H 0.5084 0.9992 -0.1562 0.048 Uiso 1 1 calc R . . C3 C 0.2905(2) 0.94790(18) -0.08279(10) 0.0397(3) Uani 1 1 d . . . H3 H 0.2022 1.0255 -0.1133 0.048 Uiso 1 1 calc R . . C4 C 0.2423(2) 0.84525(17) -0.01228(10) 0.0330(3) Uani 1 1 d . . . H4 H 0.1196 0.8526 0.0047 0.040 Uiso 1 1 calc R . . C5 C 0.37147(17) 0.73162(14) 0.03401(8) 0.0247(2) Uani 1 1 d . . . C6 C 0.32903(17) 0.60373(14) 0.10013(8) 0.0256(2) Uani 1 1 d . . . H6A H 0.4436 0.5330 0.1182 0.031 Uiso 1 1 calc R . . H6B H 0.2782 0.5411 0.0656 0.031 Uiso 1 1 calc R . . C7 C 0.30011(16) 0.70629(14) 0.29097(8) 0.0232(2) Uani 1 1 d . . . C8 C 0.47638(17) 0.71115(15) 0.26066(9) 0.0266(2) Uani 1 1 d . . . H8 H 0.5292 0.6798 0.2005 0.032 Uiso 1 1 calc R . . C9 C 0.57571(19) 0.76114(17) 0.31719(10) 0.0319(3) Uani 1 1 d . . . H9 H 0.6935 0.7648 0.2949 0.038 Uiso 1 1 calc R . . C10 C 0.5011(2) 0.80523(18) 0.40602(10) 0.0347(3) Uani 1 1 d . . . H10 H 0.5683 0.8376 0.4448 0.042 Uiso 1 1 calc R . . C11 C 0.3267(2) 0.80166(18) 0.43788(9) 0.0343(3) Uani 1 1 d . . . H11 H 0.2762 0.8318 0.4985 0.041 Uiso 1 1 calc R . . C12 C 0.22502(18) 0.75412(15) 0.38150(9) 0.0279(2) Uani 1 1 d . . . C13 C 0.0350(2) 0.7613(2) 0.42135(11) 0.0413(3) Uani 1 1 d . . . C14 C 0.12107(16) 0.46866(15) 0.23385(8) 0.0250(2) Uani 1 1 d . . . C15 C -0.02885(18) 0.47035(17) 0.19130(10) 0.0320(3) Uani 1 1 d . . . H15 H -0.0921 0.5648 0.1602 0.038 Uiso 1 1 calc R . . C16 C -0.0864(2) 0.3353(2) 0.19407(12) 0.0400(3) Uani 1 1 d . . . H16 H -0.1863 0.3388 0.1640 0.048 Uiso 1 1 calc R . . C17 C 0.0020(2) 0.1968(2) 0.24049(12) 0.0426(3) Uani 1 1 d . . . H17 H -0.0376 0.1057 0.2429 0.051 Uiso 1 1 calc R . . C18 C 0.1505(2) 0.19234(17) 0.28391(10) 0.0355(3) Uani 1 1 d . . . H18 H 0.2106 0.0979 0.3162 0.043 Uiso 1 1 calc R . . C19 C 0.21150(18) 0.32602(15) 0.28024(9) 0.0273(2) Uani 1 1 d . . . C20 C 0.3754(2) 0.31067(16) 0.32674(11) 0.0349(3) Uani 1 1 d . . . F1 F -0.02517(13) 0.65162(13) 0.39137(7) 0.0436(2) Uani 1 1 d . . . F2 F 0.0161(2) 0.7440(3) 0.51332(8) 0.0916(6) Uani 1 1 d . . . F3 F -0.08304(17) 0.90171(16) 0.39882(13) 0.0766(4) Uani 1 1 d . . . F4 F 0.33824(16) 0.39338(13) 0.40298(7) 0.0501(3) Uani 1 1 d . . . F5 F 0.49987(13) 0.36282(12) 0.26951(8) 0.0462(2) Uani 1 1 d . . . F6 F 0.45834(17) 0.16036(12) 0.35370(9) 0.0588(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 0.02381(14) 0.02120(13) 0.02109(13) -0.00041(9) -0.00532(10) -0.00403(10) O1 0.0296(4) 0.0397(5) 0.0274(4) -0.0009(4) -0.0075(4) -0.0006(4) O2 0.0297(4) 0.0269(4) 0.0345(5) -0.0004(4) -0.0102(4) 0.0003(3) N1 0.0304(5) 0.0258(5) 0.0200(4) -0.0034(3) -0.0027(4) -0.0047(4) C1 0.0413(7) 0.0327(6) 0.0258(6) -0.0032(5) 0.0035(5) -0.0122(5) C2 0.0593(9) 0.0290(6) 0.0261(6) 0.0028(5) 0.0013(6) -0.0105(6) C3 0.0530(9) 0.0297(6) 0.0283(6) 0.0050(5) -0.0091(6) -0.0002(6) C4 0.0347(6) 0.0316(6) 0.0277(6) 0.0019(5) -0.0080(5) -0.0011(5) C5 0.0298(5) 0.0235(5) 0.0190(5) -0.0017(4) -0.0043(4) -0.0040(4) C6 0.0318(6) 0.0227(5) 0.0212(5) -0.0013(4) -0.0042(4) -0.0059(4) C7 0.0269(5) 0.0220(5) 0.0203(5) -0.0006(4) -0.0044(4) -0.0060(4) C8 0.0274(5) 0.0288(5) 0.0234(5) -0.0008(4) -0.0039(4) -0.0078(4) C9 0.0303(6) 0.0351(6) 0.0327(6) 0.0003(5) -0.0098(5) -0.0113(5) C10 0.0410(7) 0.0361(7) 0.0308(6) -0.0022(5) -0.0132(5) -0.0127(6) C11 0.0432(7) 0.0376(7) 0.0241(6) -0.0060(5) -0.0053(5) -0.0127(6) C12 0.0319(6) 0.0291(5) 0.0226(5) -0.0034(4) -0.0015(4) -0.0087(5) C13 0.0412(8) 0.0531(9) 0.0315(7) -0.0141(6) 0.0074(6) -0.0184(7) C14 0.0251(5) 0.0260(5) 0.0239(5) -0.0019(4) -0.0025(4) -0.0077(4) C15 0.0265(6) 0.0351(6) 0.0359(7) -0.0049(5) -0.0060(5) -0.0093(5) C16 0.0321(7) 0.0478(8) 0.0464(8) -0.0100(7) -0.0024(6) -0.0198(6) C17 0.0480(9) 0.0435(8) 0.0442(8) -0.0058(6) 0.0036(7) -0.0283(7) C18 0.0469(8) 0.0297(6) 0.0314(6) 0.0016(5) 0.0010(6) -0.0169(6) C19 0.0323(6) 0.0261(5) 0.0233(5) 0.0010(4) -0.0022(4) -0.0094(4) C20 0.0427(7) 0.0255(6) 0.0361(7) 0.0067(5) -0.0146(6) -0.0075(5) F1 0.0377(5) 0.0539(6) 0.0436(5) -0.0111(4) 0.0043(4) -0.0215(4) F2 0.0846(10) 0.1885(18) 0.0280(5) -0.0265(8) 0.0189(6) -0.0845(11) F3 0.0404(6) 0.0520(7) 0.1248(13) -0.0239(7) 0.0192(7) -0.0020(5) F4 0.0694(7) 0.0475(5) 0.0375(5) -0.0004(4) -0.0244(5) -0.0154(5) F5 0.0317(4) 0.0470(5) 0.0597(6) 0.0087(5) -0.0127(4) -0.0118(4) F6 0.0705(7) 0.0279(4) 0.0792(8) 0.0151(5) -0.0404(6) -0.0072(5) _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 O2 1.4822(9) . ? P1 C7 1.8177(12) . ? P1 C6 1.8180(13) . ? P1 C14 1.8325(13) . ? O1 N1 1.3064(14) . ? N1 C1 1.3591(17) . ? N1 C5 1.3682(17) . ? C1 C2 1.371(2) . ? C1 H1A 0.9400 . ? C2 C3 1.381(3) . ? C2 H2 0.9400 . ? C3 C4 1.383(2) . ? C3 H3 0.9400 . ? C4 C5 1.3883(17) . ? C4 H4 0.9400 . ? C5 C6 1.4885(17) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.3970(17) . ? C7 C12 1.4089(17) . ? C8 C9 1.3905(18) . ? C8 H8 0.9400 . ? C9 C10 1.377(2) . ? C9 H9 0.9400 . ? C10 C11 1.384(2) . ? C10 H10 0.9400 . ? C11 C12 1.3911(19) . ? C11 H11 0.9400 . ? C12 C13 1.499(2) . ? C13 F2 1.319(2) . ? C13 F1 1.3284(19) . ? C13 F3 1.346(2) . ? C14 C15 1.3976(18) . ? C14 C19 1.4028(17) . ? C15 C16 1.389(2) . ? C15 H15 0.9400 . ? C16 C17 1.373(3) . ? C16 H16 0.9400 . ? C17 C18 1.388(2) . ? C17 H17 0.9400 . ? C18 C19 1.3923(19) . ? C18 H18 0.9400 . ? C19 C20 1.498(2) . ? C20 F4 1.3345(18) . ? C20 F6 1.3354(16) . ? C20 F5 1.3438(19) . ? 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 O2 P1 C7 110.83(6) . . ? O2 P1 C6 112.74(6) . . ? C7 P1 C6 108.69(6) . . ? O2 P1 C14 110.77(6) . . ? C7 P1 C14 115.13(5) . . ? C6 P1 C14 98.13(6) . . ? O1 N1 C1 118.71(12) . . ? O1 N1 C5 120.83(11) . . ? C1 N1 C5 120.43(11) . . ? N1 C1 C2 120.94(14) . . ? N1 C1 H1A 119.5 . . ? C2 C1 H1A 119.5 . . ? C1 C2 C3 120.29(13) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 118.13(13) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 121.38(14) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? N1 C5 C4 118.73(12) . . ? N1 C5 C6 117.68(10) . . ? C4 C5 C6 123.17(12) . . ? C5 C6 P1 119.53(8) . . ? C5 C6 H6A 107.4 . . ? P1 C6 H6A 107.4 . . ? C5 C6 H6B 107.4 . . ? P1 C6 H6B 107.4 . . ? H6A C6 H6B 107.0 . . ? C8 C7 C12 117.69(11) . . ? C8 C7 P1 117.46(9) . . ? C12 C7 P1 124.58(10) . . ? C9 C8 C7 121.70(12) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C10 C9 C8 119.81(13) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 119.74(13) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.99(12) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C7 120.06(12) . . ? C11 C12 C13 116.64(12) . . ? C7 C12 C13 123.28(12) . . ? F2 C13 F1 106.70(15) . . ? F2 C13 F3 106.38(16) . . ? F1 C13 F3 105.25(14) . . ? F2 C13 C12 112.15(14) . . ? F1 C13 C12 113.83(12) . . ? F3 C13 C12 111.97(14) . . ? C15 C14 C19 117.82(12) . . ? C15 C14 P1 110.74(9) . . ? C19 C14 P1 131.11(10) . . ? C16 C15 C14 121.37(14) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 120.30(14) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.46(14) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 120.81(14) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C18 C19 C14 120.23(13) . . ? C18 C19 C20 117.68(12) . . ? C14 C19 C20 122.10(11) . . ? F4 C20 F6 106.21(12) . . ? F4 C20 F5 106.52(13) . . ? F6 C20 F5 105.97(13) . . ? F4 C20 C19 112.93(13) . . ? F6 C20 C19 112.89(12) . . ? F5 C20 C19 111.80(11) . . ? 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 O1 N1 C1 C2 179.93(12) . . . . ? C5 N1 C1 C2 2.11(19) . . . . ? N1 C1 C2 C3 0.6(2) . . . . ? C1 C2 C3 C4 -2.0(2) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? O1 N1 C5 C4 179.00(11) . . . . ? C1 N1 C5 C4 -3.21(18) . . . . ? O1 N1 C5 C6 -8.14(16) . . . . ? C1 N1 C5 C6 169.65(11) . . . . ? C3 C4 C5 N1 1.7(2) . . . . ? C3 C4 C5 C6 -170.72(13) . . . . ? N1 C5 C6 P1 124.22(10) . . . . ? C4 C5 C6 P1 -63.27(15) . . . . ? O2 P1 C6 C5 45.19(12) . . . . ? C7 P1 C6 C5 -78.10(11) . . . . ? C14 P1 C6 C5 161.82(10) . . . . ? O2 P1 C7 C8 -118.67(10) . . . . ? C6 P1 C7 C8 5.75(11) . . . . ? C14 P1 C7 C8 114.64(10) . . . . ? O2 P1 C7 C12 55.17(12) . . . . ? C6 P1 C7 C12 179.60(10) . . . . ? C14 P1 C7 C12 -71.52(12) . . . . ? C12 C7 C8 C9 0.03(18) . . . . ? P1 C7 C8 C9 174.31(10) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 C11 -0.9(2) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C7 1.0(2) . . . . ? C10 C11 C12 C13 -177.45(14) . . . . ? C8 C7 C12 C11 -0.97(18) . . . . ? P1 C7 C12 C11 -174.80(10) . . . . ? C8 C7 C12 C13 177.35(13) . . . . ? P1 C7 C12 C13 3.52(19) . . . . ? C11 C12 C13 F2 -27.7(2) . . . . ? C7 C12 C13 F2 153.88(16) . . . . ? C11 C12 C13 F1 -149.02(14) . . . . ? C7 C12 C13 F1 32.6(2) . . . . ? C11 C12 C13 F3 91.75(17) . . . . ? C7 C12 C13 F3 -86.62(17) . . . . ? O2 P1 C14 C15 29.00(11) . . . . ? C7 P1 C14 C15 155.72(9) . . . . ? C6 P1 C14 C15 -89.15(10) . . . . ? O2 P1 C14 C19 -157.91(12) . . . . ? C7 P1 C14 C19 -31.19(14) . . . . ? C6 P1 C14 C19 83.94(13) . . . . ? C19 C14 C15 C16 -0.4(2) . . . . ? P1 C14 C15 C16 173.68(12) . . . . ? C14 C15 C16 C17 1.1(2) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C16 C17 C18 C19 -0.6(2) . . . . ? C17 C18 C19 C14 1.2(2) . . . . ? C17 C18 C19 C20 -178.48(14) . . . . ? C15 C14 C19 C18 -0.72(19) . . . . ? P1 C14 C19 C18 -173.41(11) . . . . ? C15 C14 C19 C20 178.97(13) . . . . ? P1 C14 C19 C20 6.3(2) . . . . ? C18 C19 C20 F4 -110.65(14) . . . . ? C14 C19 C20 F4 69.64(17) . . . . ? C18 C19 C20 F6 9.85(19) . . . . ? C14 C19 C20 F6 -169.86(13) . . . . ? C18 C19 C20 F5 129.23(13) . . . . ? C14 C19 C20 F5 -50.48(18) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 33.07 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.693 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.057