# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/399 data_k9904 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 F N O2 P' _chemical_formula_weight 369.36 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7212(4) _cell_length_b 11.5757(16) _cell_length_c 28.177(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1866.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'Denzo-SMN' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6987 _diffrn_reflns_av_R_equivalents 0.143 _diffrn_reflns_av_sigmaI/netI 0.1085 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1586 _reflns_number_gt 1123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details ? _refine_ls_number_reflns 1586 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.143 _refine_ls_shift/su_mean 0.001 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 0.6469(2) 0.89035(16) 0.81899(6) 0.0288(5) Uani 1 1 d . . . F1 F 0.7609(6) 0.6893(3) 0.78459(12) 0.0361(10) Uani 1 1 d . . . O1 O 0.7407(7) 0.9682(4) 0.86107(14) 0.0292(11) Uani 1 1 d . . . O2 O 0.3959(6) 0.8620(4) 0.82036(16) 0.0339(11) Uani 1 1 d . . . N1 N 0.7506(9) 0.9682(5) 0.77596(18) 0.0325(14) Uani 1 1 d . . . C1 C 0.8873(10) 1.0676(6) 0.7922(2) 0.0321(17) Uani 1 1 d . . . H1A H 1.0379 1.0691 0.7742 0.038 Uiso 1 1 calc R . . C2 C 0.9413(10) 1.0381(6) 0.8445(2) 0.0312(17) Uani 1 1 d . . . H2B H 1.0843 0.9885 0.8454 0.037 Uiso 1 1 calc R . . C3 C 0.9774(10) 1.1373(6) 0.8778(2) 0.0294(17) Uani 1 1 d . . . C4 C 1.1859(11) 1.2000(6) 0.8742(3) 0.046(2) Uani 1 1 d . . . H4A H 1.3008 1.1772 0.8517 0.055 Uiso 1 1 calc R . . C5 C 1.2266(12) 1.2943(7) 0.9027(3) 0.054(2) Uani 1 1 d . . . H5A H 1.3649 1.3385 0.8984 0.065 Uiso 1 1 calc R . . C6 C 1.0688(11) 1.3253(6) 0.9374(2) 0.0432(19) Uani 1 1 d . . . H6A H 1.0998 1.3886 0.9579 0.052 Uiso 1 1 calc R . . C7 C 0.8627(11) 1.2619(6) 0.9418(3) 0.0427(19) Uani 1 1 d . . . H7A H 0.7513 1.2825 0.9653 0.051 Uiso 1 1 calc R . . C8 C 0.8197(10) 1.1693(6) 0.9121(2) 0.0337(17) Uani 1 1 d . . . H8A H 0.6783 1.1270 0.9155 0.040 Uiso 1 1 calc R . . C9 C 0.8247(10) 0.7591(5) 0.8239(2) 0.0290(15) Uani 1 1 d . . . H9A H 0.9934 0.7804 0.8211 0.035 Uiso 1 1 calc R . . C10 C 0.7891(9) 0.6937(6) 0.8693(2) 0.0237(15) Uani 1 1 d . . . C11 C 0.9555(10) 0.7007(5) 0.9045(2) 0.0259(15) Uani 1 1 d . . . H11A H 1.0959 0.7424 0.8990 0.031 Uiso 1 1 calc R . . C12 C 0.9186(9) 0.6460(5) 0.9490(2) 0.0243(15) Uani 1 1 d . . . C13 C 1.0807(10) 0.6558(6) 0.9871(2) 0.0277(16) Uani 1 1 d . . . H13A H 1.2204 0.6989 0.9826 0.033 Uiso 1 1 calc R . . C14 C 1.0407(10) 0.6055(6) 1.0294(2) 0.0314(16) Uani 1 1 d . . . H14A H 1.1517 0.6132 1.0543 0.038 Uiso 1 1 calc R . . C15 C 0.8329(10) 0.5409(6) 1.0369(2) 0.0333(17) Uani 1 1 d . . . H15A H 0.8054 0.5056 1.0668 0.040 Uiso 1 1 calc R . . C16 C 0.6726(10) 0.5293(5) 1.0014(2) 0.0271(15) Uani 1 1 d . . . H16A H 0.5354 0.4848 1.0065 0.033 Uiso 1 1 calc R . . C17 C 0.7098(10) 0.5830(5) 0.9571(2) 0.0281(16) Uani 1 1 d . . . C18 C 0.5448(10) 0.5763(6) 0.9191(2) 0.0290(17) Uani 1 1 d . . . H18A H 0.4062 0.5322 0.9232 0.035 Uiso 1 1 calc R . . C19 C 0.5810(9) 0.6308(6) 0.8776(2) 0.0285(16) Uani 1 1 d . . . H19A H 0.4650 0.6272 0.8535 0.034 Uiso 1 1 calc R . . C20 C 0.6950(13) 0.9547(7) 0.7257(2) 0.053(2) Uani 1 1 d . . . H20A H 0.8401 0.9517 0.7072 0.079 Uiso 1 1 calc R . . H20B H 0.6005 1.0204 0.7151 0.079 Uiso 1 1 calc R . . H20C H 0.6070 0.8830 0.7210 0.079 Uiso 1 1 calc R . . C21 C 0.7634(11) 1.1833(6) 0.7849(3) 0.0433(19) Uani 1 1 d . . . H21A H 0.7213 1.1920 0.7514 0.065 Uiso 1 1 calc R . . H21B H 0.8679 1.2463 0.7943 0.065 Uiso 1 1 calc R . . H21C H 0.6215 1.1857 0.8044 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0230(8) 0.0350(11) 0.0284(10) 0.0010(10) 0.0001(7) 0.0018(8) F1 0.0360(19) 0.043(2) 0.029(2) -0.007(2) -0.0002(17) 0.0056(18) O1 0.025(2) 0.033(3) 0.030(3) 0.000(2) 0.0006(19) -0.007(2) O2 0.0129(19) 0.045(3) 0.044(3) -0.003(3) 0.0027(19) -0.0014(18) N1 0.031(3) 0.043(4) 0.024(3) 0.005(3) -0.002(2) -0.007(3) C1 0.027(3) 0.036(5) 0.033(4) 0.007(3) 0.007(3) 0.007(3) C2 0.019(3) 0.032(4) 0.042(4) 0.005(4) 0.010(3) 0.001(3) C3 0.019(3) 0.029(4) 0.040(4) -0.001(3) 0.004(3) 0.003(3) C4 0.031(4) 0.036(5) 0.071(6) -0.017(4) 0.016(4) -0.003(3) C5 0.024(4) 0.042(5) 0.096(7) -0.014(5) 0.010(4) -0.011(4) C6 0.042(4) 0.036(5) 0.052(5) -0.012(4) -0.003(4) -0.002(4) C7 0.036(4) 0.045(5) 0.047(4) -0.009(4) 0.010(3) -0.002(4) C8 0.026(4) 0.033(4) 0.042(4) -0.003(4) -0.001(3) -0.004(3) C9 0.026(3) 0.028(4) 0.033(4) -0.008(4) -0.002(3) -0.002(3) C10 0.018(3) 0.030(4) 0.023(4) 0.001(3) 0.002(3) 0.005(3) C11 0.021(3) 0.019(4) 0.037(4) -0.003(3) 0.003(3) -0.002(3) C12 0.022(3) 0.017(4) 0.034(4) 0.001(3) 0.001(3) 0.002(3) C13 0.021(3) 0.027(4) 0.036(4) 0.000(3) 0.003(3) -0.001(3) C14 0.025(3) 0.039(5) 0.030(4) -0.001(4) -0.003(3) 0.002(3) C15 0.034(4) 0.032(4) 0.035(4) 0.006(3) 0.006(3) 0.007(3) C16 0.023(3) 0.022(4) 0.037(4) 0.005(3) 0.005(3) 0.006(3) C17 0.023(3) 0.021(4) 0.040(4) -0.006(3) 0.003(3) 0.003(3) C18 0.019(3) 0.026(4) 0.041(4) -0.007(3) 0.004(3) -0.007(3) C19 0.023(3) 0.035(4) 0.027(4) -0.002(3) 0.003(3) 0.004(3) C20 0.067(5) 0.056(6) 0.036(5) 0.007(4) 0.005(4) 0.003(4) C21 0.037(4) 0.041(5) 0.051(5) 0.019(4) 0.006(3) 0.013(4) _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 1.474(4) . ? P1 O1 1.583(4) . ? P1 N1 1.623(5) . ? P1 C9 1.834(6) . ? F1 C9 1.420(7) . ? O1 C2 1.480(7) . ? N1 C20 1.461(8) . ? N1 C1 1.464(8) . ? C1 C21 1.529(9) . ? C1 C2 1.545(8) . ? C2 C3 1.496(9) . ? C3 C8 1.373(8) . ? C3 C4 1.401(9) . ? C4 C5 1.375(10) . ? C5 C6 1.379(10) . ? C6 C7 1.394(9) . ? C7 C8 1.382(9) . ? C9 C10 1.498(9) . ? C10 C11 1.378(8) . ? C10 C19 1.415(8) . ? C11 C12 1.420(8) . ? C12 C17 1.418(8) . ? C12 C13 1.424(8) . ? C13 C14 1.347(8) . ? C14 C15 1.420(9) . ? C15 C16 1.364(8) . ? C16 C17 1.411(9) . ? C17 C18 1.430(8) . ? C18 C19 1.345(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 P1 O1 116.0(2) . . ? O2 P1 N1 120.0(3) . . ? O1 P1 N1 96.9(2) . . ? O2 P1 C9 110.7(3) . . ? O1 P1 C9 103.1(3) . . ? N1 P1 C9 108.3(3) . . ? C2 O1 P1 109.8(4) . . ? C20 N1 C1 120.2(5) . . ? C20 N1 P1 125.9(5) . . ? C1 N1 P1 113.5(4) . . ? N1 C1 C21 113.5(5) . . ? N1 C1 C2 103.4(5) . . ? C21 C1 C2 114.5(5) . . ? O1 C2 C3 109.2(5) . . ? O1 C2 C1 105.4(5) . . ? C3 C2 C1 117.1(6) . . ? C8 C3 C4 118.1(6) . . ? C8 C3 C2 123.9(5) . . ? C4 C3 C2 118.0(6) . . ? C5 C4 C3 120.9(7) . . ? C4 C5 C6 120.7(7) . . ? C5 C6 C7 118.7(7) . . ? C8 C7 C6 120.4(7) . . ? C3 C8 C7 121.2(6) . . ? F1 C9 C10 110.1(5) . . ? F1 C9 P1 105.6(4) . . ? C10 C9 P1 114.1(4) . . ? C11 C10 C19 119.5(6) . . ? C11 C10 C9 119.4(5) . . ? C19 C10 C9 121.0(5) . . ? C10 C11 C12 120.5(5) . . ? C17 C12 C11 119.8(5) . . ? C17 C12 C13 117.9(6) . . ? C11 C12 C13 122.2(5) . . ? C14 C13 C12 121.5(6) . . ? C13 C14 C15 120.1(6) . . ? C16 C15 C14 120.4(6) . . ? C15 C16 C17 120.3(6) . . ? C16 C17 C12 119.8(6) . . ? C16 C17 C18 122.6(5) . . ? C12 C17 C18 117.6(5) . . ? C19 C18 C17 121.6(5) . . ? C18 C19 C10 121.0(6) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.303 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.056 data_k99100a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 F N O2 P' _chemical_formula_weight 395.39 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 11.8451(5) _cell_length_b 27.3815(19) _cell_length_c 6.0985(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1978.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9439 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details 'Denzo-SMN' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9348 _diffrn_reflns_av_R_equivalents 0.090 _diffrn_reflns_av_sigmaI/netI 0.1284 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.31 _reflns_number_total 3440 _reflns_number_gt 2159 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(16) _refine_ls_number_reflns 3440 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1102 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _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 0.36707(7) 0.71647(3) 0.77471(19) 0.0267(3) Uani 1 1 d . . . F1 F 0.25820(16) 0.63824(7) 0.8996(4) 0.0375(6) Uani 1 1 d . . . O1 O 0.43175(18) 0.73114(7) 0.5566(5) 0.0271(7) Uani 1 1 d . . . O2 O 0.43145(17) 0.71509(9) 0.9798(4) 0.0321(7) Uani 1 1 d . . . N1 N 0.2670(2) 0.75800(10) 0.7559(6) 0.0261(8) Uani 1 1 d . . . C1 C 0.2543(3) 0.77243(12) 0.5243(7) 0.0256(10) Uani 1 1 d . . . H1A H 0.2109 0.7463 0.4464 0.031 Uiso 1 1 calc R . . C2 C 0.3766(3) 0.77189(11) 0.4389(7) 0.0266(9) Uani 1 1 d . . . H2B H 0.3756 0.7642 0.2787 0.032 Uiso 1 1 calc R . . C3 C 0.4432(3) 0.81852(12) 0.4736(7) 0.0249(10) Uani 1 1 d . . . C4 C 0.4428(3) 0.85335(13) 0.3069(7) 0.0297(11) Uani 1 1 d . . . H4A H 0.4024 0.8471 0.1753 0.036 Uiso 1 1 calc R . . C5 C 0.5003(3) 0.89685(14) 0.3307(7) 0.0347(11) Uani 1 1 d . . . H5A H 0.4987 0.9204 0.2164 0.042 Uiso 1 1 calc R . . C6 C 0.5608(3) 0.90628(13) 0.5220(8) 0.0334(11) Uani 1 1 d . . . H6A H 0.6007 0.9361 0.5388 0.040 Uiso 1 1 calc R . . C7 C 0.5621(3) 0.87160(13) 0.6874(7) 0.0318(11) Uani 1 1 d . . . H7A H 0.6031 0.8778 0.8183 0.038 Uiso 1 1 calc R . . C8 C 0.5038(3) 0.82791(13) 0.6633(7) 0.0286(10) Uani 1 1 d . . . H8A H 0.5056 0.8043 0.7776 0.034 Uiso 1 1 calc R . . C9 C 0.3110(3) 0.65618(12) 0.7066(7) 0.0280(11) Uani 1 1 d . . . H9A H 0.2525 0.6599 0.5896 0.034 Uiso 1 1 calc R . . C10 C 0.3986(3) 0.62026(12) 0.6293(7) 0.0247(10) Uani 1 1 d . . . C11 C 0.4853(3) 0.60540(12) 0.7664(7) 0.0249(10) Uani 1 1 d . . . H11A H 0.4896 0.6183 0.9107 0.030 Uiso 1 1 calc R . . C12 C 0.5666(3) 0.57193(12) 0.6974(7) 0.0256(10) Uani 1 1 d . . . C13 C 0.5586(3) 0.55460(12) 0.4841(8) 0.0296(10) Uani 1 1 d . . . H13A H 0.6137 0.5321 0.4329 0.036 Uiso 1 1 calc R . . C14 C 0.4734(3) 0.56898(13) 0.3436(8) 0.0332(11) Uani 1 1 d . . . H14A H 0.4698 0.5565 0.1984 0.040 Uiso 1 1 calc R . . C15 C 0.3927(3) 0.60201(13) 0.4183(8) 0.0304(11) Uani 1 1 d . . . H15A H 0.3333 0.6120 0.3238 0.036 Uiso 1 1 calc R . . C16 C 0.6588(3) 0.55482(13) 0.8442(7) 0.0283(11) Uani 1 1 d . . . C17 C 0.6958(3) 0.50614(13) 0.8352(7) 0.0365(12) Uani 1 1 d . . . H17A H 0.6618 0.4840 0.7349 0.044 Uiso 1 1 calc R . . C18 C 0.7816(3) 0.49026(14) 0.9720(8) 0.0402(12) Uani 1 1 d . . . H18A H 0.8056 0.4572 0.9653 0.048 Uiso 1 1 calc R . . C19 C 0.8326(3) 0.52176(14) 1.1175(8) 0.0375(12) Uani 1 1 d . . . H19A H 0.8923 0.5107 1.2092 0.045 Uiso 1 1 calc R . . C20 C 0.7962(3) 0.56953(14) 1.1287(7) 0.0331(11) Uani 1 1 d . . . H20A H 0.8309 0.5914 1.2289 0.040 Uiso 1 1 calc R . . C21 C 0.7095(3) 0.58592(14) 0.9953(7) 0.0317(11) Uani 1 1 d . . . H21A H 0.6844 0.6188 1.0071 0.038 Uiso 1 1 calc R . . C22 C 0.1646(3) 0.75424(14) 0.8898(7) 0.0362(11) Uani 1 1 d . . . H22A H 0.1291 0.7865 0.9018 0.054 Uiso 1 1 calc R . . H22B H 0.1844 0.7424 1.0364 0.054 Uiso 1 1 calc R . . H22C H 0.1118 0.7314 0.8207 0.054 Uiso 1 1 calc R . . C23 C 0.1929(3) 0.82033(12) 0.4950(8) 0.0343(11) Uani 1 1 d . . . H23A H 0.1149 0.8169 0.5464 0.051 Uiso 1 1 calc R . . H23B H 0.1929 0.8293 0.3395 0.051 Uiso 1 1 calc R . . H23C H 0.2311 0.8458 0.5801 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0207(4) 0.0326(5) 0.0268(8) -0.0025(5) -0.0007(5) 0.0007(4) F1 0.0314(12) 0.0423(13) 0.0389(17) 0.0074(12) 0.0073(12) 0.0003(10) O1 0.0241(12) 0.0294(14) 0.028(2) 0.0046(12) 0.0037(13) 0.0035(11) O2 0.0241(13) 0.0446(15) 0.0276(19) -0.0050(15) -0.0038(14) 0.0008(12) N1 0.0215(14) 0.0329(17) 0.024(2) -0.0031(17) 0.0035(17) 0.0008(12) C1 0.0219(19) 0.026(2) 0.029(3) -0.0088(19) -0.0006(19) -0.0023(15) C2 0.0279(19) 0.034(2) 0.018(3) -0.0029(18) -0.0044(19) -0.0015(17) C3 0.0205(18) 0.028(2) 0.026(3) -0.005(2) -0.002(2) 0.0036(16) C4 0.0234(19) 0.037(2) 0.029(3) 0.002(2) -0.004(2) -0.0004(17) C5 0.035(2) 0.036(2) 0.034(3) 0.008(2) 0.003(2) -0.0027(19) C6 0.031(2) 0.027(2) 0.042(3) -0.003(2) 0.004(2) -0.0047(17) C7 0.0219(19) 0.037(2) 0.036(3) -0.006(2) 0.002(2) 0.0001(17) C8 0.0214(18) 0.032(2) 0.032(3) 0.000(2) 0.002(2) 0.0040(17) C9 0.0235(18) 0.034(2) 0.027(3) 0.010(2) -0.001(2) -0.0009(16) C10 0.024(2) 0.023(2) 0.027(3) -0.001(2) 0.0045(18) -0.0069(16) C11 0.0216(18) 0.029(2) 0.024(3) -0.0001(19) -0.002(2) -0.0058(16) C12 0.0207(19) 0.025(2) 0.032(3) -0.001(2) 0.001(2) -0.0062(16) C13 0.026(2) 0.027(2) 0.037(3) -0.001(2) 0.009(2) -0.0001(16) C14 0.039(2) 0.034(2) 0.027(3) -0.002(2) 0.005(2) -0.0041(18) C15 0.031(2) 0.028(2) 0.032(3) 0.006(2) -0.002(2) -0.0063(17) C16 0.022(2) 0.033(2) 0.029(3) 0.003(2) 0.0079(19) -0.0007(17) C17 0.026(2) 0.034(2) 0.049(4) 0.002(2) -0.003(2) -0.0006(18) C18 0.034(2) 0.029(2) 0.057(4) 0.002(2) -0.004(2) 0.0061(18) C19 0.021(2) 0.046(3) 0.045(3) 0.010(2) -0.001(2) 0.0057(18) C20 0.029(2) 0.038(2) 0.032(3) -0.002(2) 0.004(2) -0.0021(18) C21 0.028(2) 0.030(2) 0.038(3) 0.006(2) 0.004(2) 0.0047(17) C22 0.027(2) 0.047(2) 0.034(3) -0.003(2) 0.004(2) 0.0036(18) C23 0.028(2) 0.036(2) 0.039(3) -0.002(2) -0.005(2) 0.0045(17) _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 1.466(3) . ? P1 O1 1.587(3) . ? P1 N1 1.647(3) . ? P1 C9 1.827(3) . ? F1 C9 1.420(4) . ? O1 C2 1.478(4) . ? N1 C22 1.466(4) . ? N1 C1 1.474(5) . ? C1 C23 1.510(4) . ? C1 C2 1.540(5) . ? C2 C3 1.515(4) . ? C3 C8 1.386(5) . ? C3 C4 1.394(5) . ? C4 C5 1.380(5) . ? C5 C6 1.393(6) . ? C6 C7 1.386(5) . ? C7 C8 1.389(5) . ? C9 C10 1.505(5) . ? C10 C15 1.382(5) . ? C10 C11 1.386(5) . ? C11 C12 1.394(5) . ? C12 C13 1.388(6) . ? C12 C16 1.488(5) . ? C13 C14 1.382(5) . ? C14 C15 1.393(5) . ? C16 C21 1.391(5) . ? C16 C17 1.404(5) . ? C17 C18 1.385(5) . ? C18 C19 1.378(6) . ? C19 C20 1.379(5) . ? C20 C21 1.385(5) . ? 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 O1 118.09(13) . . ? O2 P1 N1 116.86(16) . . ? O1 P1 N1 96.56(15) . . ? O2 P1 C9 111.09(17) . . ? O1 P1 C9 102.34(16) . . ? N1 P1 C9 110.27(15) . . ? C2 O1 P1 112.6(2) . . ? C22 N1 C1 117.9(3) . . ? C22 N1 P1 120.6(3) . . ? C1 N1 P1 109.0(2) . . ? N1 C1 C23 113.3(3) . . ? N1 C1 C2 103.0(3) . . ? C23 C1 C2 114.9(3) . . ? O1 C2 C3 109.8(3) . . ? O1 C2 C1 105.0(3) . . ? C3 C2 C1 115.7(3) . . ? C8 C3 C4 118.9(3) . . ? C8 C3 C2 122.8(4) . . ? C4 C3 C2 118.2(4) . . ? C5 C4 C3 120.8(4) . . ? C4 C5 C6 120.1(4) . . ? C7 C6 C5 119.2(3) . . ? C6 C7 C8 120.5(4) . . ? C3 C8 C7 120.4(4) . . ? F1 C9 C10 109.7(3) . . ? F1 C9 P1 106.5(2) . . ? C10 C9 P1 114.3(2) . . ? C15 C10 C11 119.5(3) . . ? C15 C10 C9 119.5(3) . . ? C11 C10 C9 120.9(4) . . ? C10 C11 C12 121.5(4) . . ? C13 C12 C11 117.4(3) . . ? C13 C12 C16 120.4(3) . . ? C11 C12 C16 122.2(4) . . ? C14 C13 C12 122.2(4) . . ? C13 C14 C15 118.9(4) . . ? C10 C15 C14 120.3(4) . . ? C21 C16 C17 118.2(4) . . ? C21 C16 C12 121.5(3) . . ? C17 C16 C12 120.3(4) . . ? C18 C17 C16 120.2(4) . . ? C19 C18 C17 120.9(4) . . ? C18 C19 C20 119.2(4) . . ? C19 C20 C21 120.7(4) . . ? C20 C21 C16 120.7(3) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.334 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.053 data_k9963 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 F N O2 P' _chemical_formula_weight 319.30 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7208(2) _cell_length_b 11.2412(8) _cell_length_c 24.5839(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1580.96(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9539 _exptl_absorpt_correction_T_max 0.9629 _exptl_absorpt_process_details 'Denzo-SMN' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7844 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_av_sigmaI/netI 0.0914 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3556 _reflns_number_gt 2660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.009(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(11) _refine_ls_number_reflns 3556 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.774 _refine_ls_shift/su_mean 0.004 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 0.16233(11) 0.66480(6) 0.16345(3) 0.02405(17) Uani 1 1 d . . . F1 F 0.2539(3) 0.88389(14) 0.19195(5) 0.0336(4) Uani 1 1 d . . . O1 O -0.0876(3) 0.69166(16) 0.15826(8) 0.0309(4) Uani 1 1 d . . . O2 O 0.2677(3) 0.57474(15) 0.12008(6) 0.0248(4) Uani 1 1 d . . . N1 N 0.2545(4) 0.5944(2) 0.21719(8) 0.0292(5) Uani 1 1 d . . . C1 C 0.4031(4) 0.4911(2) 0.20512(10) 0.0244(6) Uani 1 1 d . . . H1A H 0.5503 0.4980 0.2268 0.029 Uiso 1 1 calc R . . C2 C 0.4634(4) 0.5082(2) 0.14432(9) 0.0230(6) Uani 1 1 d . . . H2A H 0.6079 0.5579 0.1416 0.028 Uiso 1 1 calc R . . C3 C 0.3389(4) 0.7999(2) 0.15410(10) 0.0254(5) Uani 1 1 d . . . H3A H 0.5050 0.7810 0.1635 0.030 Uiso 1 1 calc R . . C4 C 0.3317(4) 0.8483(2) 0.09739(9) 0.0223(5) Uani 1 1 d . . . C5 C 0.5167(4) 0.8244(2) 0.06196(10) 0.0236(5) Uani 1 1 d . . . H5A H 0.6493 0.7821 0.0749 0.028 Uiso 1 1 calc R . . C6 C 0.5101(4) 0.8609(2) 0.00898(10) 0.0271(6) Uani 1 1 d . . . H6A H 0.6358 0.8423 -0.0148 0.033 Uiso 1 1 calc R . . C7 C 0.3205(5) 0.9250(2) -0.01013(10) 0.0273(6) Uani 1 1 d . . . H7A H 0.3171 0.9514 -0.0468 0.033 Uiso 1 1 calc R . . C8 C 0.1348(4) 0.9505(2) 0.02459(11) 0.0279(6) Uani 1 1 d . . . H8A H 0.0047 0.9947 0.0116 0.034 Uiso 1 1 calc R . . C9 C 0.1391(4) 0.9121(2) 0.07770(10) 0.0262(6) Uani 1 1 d . . . H9A H 0.0111 0.9288 0.1011 0.031 Uiso 1 1 calc R . . C10 C 0.5023(4) 0.3950(2) 0.11319(9) 0.0218(5) Uani 1 1 d . . . C11 C 0.3335(4) 0.3446(2) 0.07974(9) 0.0243(5) Uani 1 1 d . . . H11A H 0.1908 0.3854 0.0732 0.029 Uiso 1 1 calc R . . C12 C 0.3733(4) 0.2347(2) 0.05583(11) 0.0297(6) Uani 1 1 d . . . H12A H 0.2571 0.2004 0.0331 0.036 Uiso 1 1 calc R . . C13 C 0.5811(4) 0.1746(3) 0.06484(10) 0.0286(6) Uani 1 1 d . . . H13A H 0.6053 0.0983 0.0491 0.034 Uiso 1 1 calc R . . C14 C 0.7527(5) 0.2254(2) 0.09658(10) 0.0288(6) Uani 1 1 d . . . H14A H 0.8968 0.1853 0.1022 0.035 Uiso 1 1 calc R . . C15 C 0.7134(4) 0.3363(2) 0.12041(10) 0.0273(6) Uani 1 1 d . . . H15A H 0.8325 0.3720 0.1418 0.033 Uiso 1 1 calc R . . C16 C 0.2841(5) 0.3750(2) 0.21971(10) 0.0306(6) Uani 1 1 d . . . H16A H 0.2337 0.3775 0.2578 0.046 Uiso 1 1 calc R . . H16B H 0.3939 0.3090 0.2146 0.046 Uiso 1 1 calc R . . H16C H 0.1477 0.3633 0.1962 0.046 Uiso 1 1 calc R . . C17 C 0.1832(5) 0.6184(3) 0.27298(10) 0.0373(7) Uani 1 1 d . . . H17A H 0.3214 0.6198 0.2965 0.056 Uiso 1 1 calc R . . H17B H 0.0762 0.5559 0.2853 0.056 Uiso 1 1 calc R . . H17C H 0.1040 0.6956 0.2747 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0222(3) 0.0235(3) 0.0265(3) 0.0000(3) -0.0008(3) -0.0002(3) F1 0.0398(8) 0.0295(9) 0.0316(8) -0.0092(7) 0.0010(7) 0.0002(7) O1 0.0206(8) 0.0293(10) 0.0428(11) 0.0040(9) -0.0031(8) -0.0015(7) O2 0.0268(9) 0.0235(9) 0.0240(9) 0.0015(7) -0.0046(7) 0.0038(7) N1 0.0370(11) 0.0278(13) 0.0229(11) 0.0002(9) 0.0041(9) 0.0077(10) C1 0.0210(12) 0.0280(15) 0.0243(14) 0.0033(12) -0.0038(10) 0.0001(11) C2 0.0207(11) 0.0218(13) 0.0266(14) 0.0021(11) -0.0040(10) 0.0000(11) C3 0.0232(11) 0.0239(12) 0.0290(14) -0.0051(10) -0.0008(11) 0.0018(11) C4 0.0215(11) 0.0176(12) 0.0278(13) -0.0032(10) -0.0020(11) -0.0056(11) C5 0.0203(11) 0.0193(13) 0.0312(14) -0.0009(11) -0.0015(10) -0.0010(11) C6 0.0251(13) 0.0243(15) 0.0319(15) -0.0043(11) 0.0015(10) -0.0030(11) C7 0.0317(14) 0.0218(13) 0.0284(14) 0.0020(11) -0.0063(12) -0.0058(12) C8 0.0259(14) 0.0223(13) 0.0356(16) 0.0027(11) -0.0079(12) -0.0019(11) C9 0.0212(12) 0.0233(13) 0.0341(15) -0.0033(12) 0.0021(11) 0.0002(11) C10 0.0223(12) 0.0211(13) 0.0219(13) 0.0025(10) 0.0020(9) -0.0028(11) C11 0.0223(11) 0.0244(12) 0.0262(13) -0.0005(11) -0.0010(10) -0.0008(12) C12 0.0284(14) 0.0288(15) 0.0318(15) -0.0019(12) -0.0015(11) -0.0040(12) C13 0.0337(14) 0.0200(13) 0.0320(15) 0.0027(12) 0.0037(11) 0.0009(11) C14 0.0278(12) 0.0267(14) 0.0318(15) 0.0043(12) 0.0021(11) 0.0050(11) C15 0.0243(13) 0.0275(13) 0.0301(14) -0.0019(12) -0.0006(10) -0.0027(12) C16 0.0353(15) 0.0322(15) 0.0242(14) 0.0051(12) -0.0010(11) -0.0033(12) C17 0.0480(17) 0.0365(16) 0.0274(15) 0.0008(13) 0.0057(13) 0.0097(15) _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 1.4670(17) . ? P1 O2 1.5890(18) . ? P1 N1 1.628(2) . ? P1 C3 1.839(3) . ? F1 C3 1.412(3) . ? O2 C2 1.472(3) . ? N1 C17 1.456(3) . ? N1 C1 1.469(3) . ? C1 C16 1.516(4) . ? C1 C2 1.546(3) . ? C2 C10 1.501(3) . ? C3 C4 1.497(3) . ? C4 C5 1.397(3) . ? C4 C9 1.401(3) . ? C5 C6 1.366(3) . ? C6 C7 1.384(4) . ? C7 C8 1.393(4) . ? C8 C9 1.376(4) . ? C10 C15 1.387(3) . ? C10 C11 1.389(3) . ? C11 C12 1.387(4) . ? C12 C13 1.386(4) . ? C13 C14 1.378(4) . ? C14 C15 1.396(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 116.27(10) . . ? O1 P1 N1 119.10(11) . . ? O2 P1 N1 96.42(10) . . ? O1 P1 C3 110.77(11) . . ? O2 P1 C3 103.53(10) . . ? N1 P1 C3 108.98(12) . . ? C2 O2 P1 109.92(14) . . ? C17 N1 C1 119.9(2) . . ? C17 N1 P1 125.70(18) . . ? C1 N1 P1 114.06(16) . . ? N1 C1 C16 111.9(2) . . ? N1 C1 C2 103.09(19) . . ? C16 C1 C2 115.8(2) . . ? O2 C2 C10 109.70(18) . . ? O2 C2 C1 106.54(19) . . ? C10 C2 C1 114.9(2) . . ? F1 C3 C4 111.18(19) . . ? F1 C3 P1 106.30(16) . . ? C4 C3 P1 113.66(16) . . ? C5 C4 C9 118.6(2) . . ? C5 C4 C3 119.3(2) . . ? C9 C4 C3 122.0(2) . . ? C6 C5 C4 121.0(2) . . ? C5 C6 C7 120.1(2) . . ? C6 C7 C8 119.8(2) . . ? C9 C8 C7 120.2(2) . . ? C8 C9 C4 120.2(2) . . ? C15 C10 C11 119.1(2) . . ? C15 C10 C2 117.8(2) . . ? C11 C10 C2 123.0(2) . . ? C12 C11 C10 120.0(2) . . ? C13 C12 C11 120.5(3) . . ? C14 C13 C12 119.9(3) . . ? C13 C14 C15 119.6(2) . . ? C10 C15 C14 120.7(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.236 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.052 data_k98210 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 F N O2 P' _chemical_formula_weight 369.36 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.6666(4) _cell_length_b 12.1266(5) _cell_length_c 11.6697(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.744(3) _cell_angle_gamma 90.00 _cell_volume 936.89(8) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9379 _exptl_absorpt_correction_T_max 0.9569 _exptl_absorpt_process_details 'Denzo-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6432 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.39 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3690 _reflns_number_gt 3326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.1195P] 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 SHELXL _refine_ls_extinction_coef 0.027(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 3690 _refine_ls_number_parameters 239 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.073 _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 0.58791(6) 0.88335(4) 0.54802(4) 0.03912(13) Uani 1 1 d . . . F1 F 0.80393(19) 0.83854(12) 0.74620(11) 0.0682(4) Uani 1 1 d . . . O1 O 0.75208(17) 0.97639(10) 0.53881(11) 0.0389(3) Uani 1 1 d . . . O2 O 0.37717(18) 0.90803(11) 0.50595(12) 0.0496(4) Uani 1 1 d . . . N1 N 0.6992(2) 0.78772(12) 0.48111(14) 0.0422(4) Uani 1 1 d . . . C1 C 0.9131(3) 0.81413(15) 0.47445(17) 0.0394(4) Uani 1 1 d . . . H1A H 0.9942 0.7897 0.5476 0.047 Uiso 1 1 calc R . . C2 C 0.9133(3) 0.94214(16) 0.47041(16) 0.0375(4) Uani 1 1 d . . . H2B H 1.0453 0.9690 0.5102 0.045 Uiso 1 1 calc R . . C3 C 0.8798(3) 0.99445(16) 0.35268(16) 0.0404(4) Uani 1 1 d . . . C4 C 1.0453(3) 1.0096(2) 0.29211(19) 0.0541(5) Uani 1 1 d . . . H4A H 1.1750 0.9849 0.3244 0.065 Uiso 1 1 calc R . . C5 C 1.0224(4) 1.0601(2) 0.1854(2) 0.0693(7) Uani 1 1 d . . . H5A H 1.1371 1.0703 0.1453 0.083 Uiso 1 1 calc R . . C6 C 0.8376(4) 1.0956(2) 0.1364(2) 0.0688(7) Uani 1 1 d . . . H6A H 0.8236 1.1310 0.0633 0.083 Uiso 1 1 calc R . . C7 C 0.6706(3) 1.0793(2) 0.1948(2) 0.0617(6) Uani 1 1 d . . . H7A H 0.5411 1.1029 0.1611 0.074 Uiso 1 1 calc R . . C8 C 0.6919(3) 1.02865(17) 0.30253(18) 0.0496(5) Uani 1 1 d . . . H8A H 0.5766 1.0175 0.3419 0.060 Uiso 1 1 calc R . . C9 C 0.6011(3) 0.85660(17) 0.70283(18) 0.0512(5) Uani 1 1 d . . . H9A H 0.5234 0.7877 0.7142 0.061 Uiso 1 1 calc R . . C10 C 0.5117(3) 0.94825(17) 0.76598(17) 0.0488(5) Uani 1 1 d . . . C11 C 0.6126(3) 1.04400(18) 0.78698(17) 0.0515(5) Uani 1 1 d . . . H11A H 0.7438 1.0519 0.7638 0.062 Uiso 1 1 calc R . . C12 C 0.5250(3) 1.1343(2) 0.84377(18) 0.0547(5) Uani 1 1 d . . . C13 C 0.6253(5) 1.2360(2) 0.8624(2) 0.0700(7) Uani 1 1 d . . . H13A H 0.7546 1.2462 0.8374 0.084 Uiso 1 1 calc R . . C14 C 0.5377(5) 1.3195(3) 0.9160(2) 0.0812(8) Uani 1 1 d . . . H14A H 0.6057 1.3882 0.9270 0.097 Uiso 1 1 calc R . . C15 C 0.3489(6) 1.3060(3) 0.9550(2) 0.0867(9) Uani 1 1 d . . . H15A H 0.2916 1.3648 0.9941 0.104 Uiso 1 1 calc R . . C16 C 0.2471(5) 1.2097(3) 0.9377(2) 0.0773(8) Uani 1 1 d . . . H16A H 0.1184 1.2016 0.9640 0.093 Uiso 1 1 calc R . . C17 C 0.3329(4) 1.1193(2) 0.87936(17) 0.0571(6) Uani 1 1 d . . . C18 C 0.2310(3) 1.0195(2) 0.8561(2) 0.0673(7) Uani 1 1 d . . . H18A H 0.1002 1.0099 0.8793 0.081 Uiso 1 1 calc R . . C19 C 0.3169(3) 0.9353(2) 0.8003(2) 0.0584(6) Uani 1 1 d . . . H19A H 0.2453 0.8682 0.7848 0.070 Uiso 1 1 calc R . . C20 C 0.6307(3) 0.67398(17) 0.4752(2) 0.0568(6) Uani 1 1 d . . . H20A H 0.6550 0.6421 0.4009 0.085 Uiso 1 1 calc R . . H20B H 0.4859 0.6714 0.4828 0.085 Uiso 1 1 calc R . . H20C H 0.7050 0.6317 0.5380 0.085 Uiso 1 1 calc R . . C21 C 0.9957(3) 0.75825(18) 0.37366(19) 0.0533(5) Uani 1 1 d . . . H21A H 0.9990 0.6783 0.3859 0.080 Uiso 1 1 calc R . . H21B H 1.1327 0.7851 0.3677 0.080 Uiso 1 1 calc R . . H21C H 0.9087 0.7753 0.3022 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0328(2) 0.0350(2) 0.0490(3) 0.0043(2) 0.00249(17) 0.0006(2) F1 0.0611(8) 0.0803(9) 0.0601(8) 0.0109(6) -0.0050(6) 0.0291(6) O1 0.0373(6) 0.0318(6) 0.0483(7) -0.0026(6) 0.0082(5) -0.0007(5) O2 0.0330(6) 0.0537(9) 0.0613(8) 0.0065(6) 0.0017(6) 0.0013(6) N1 0.0362(8) 0.0318(8) 0.0578(10) -0.0010(7) 0.0026(7) -0.0033(6) C1 0.0356(10) 0.0336(10) 0.0481(11) -0.0013(8) 0.0011(8) 0.0035(7) C2 0.0301(9) 0.0411(10) 0.0411(10) -0.0016(7) 0.0027(8) 0.0000(7) C3 0.0391(9) 0.0376(9) 0.0437(10) -0.0015(7) 0.0011(8) -0.0025(8) C4 0.0409(10) 0.0703(14) 0.0511(12) 0.0092(10) 0.0049(9) -0.0042(10) C5 0.0586(13) 0.093(2) 0.0559(13) 0.0203(13) 0.0075(11) -0.0105(13) C6 0.0753(16) 0.0768(17) 0.0519(13) 0.0192(13) -0.0023(12) -0.0042(13) C7 0.0585(13) 0.0648(14) 0.0583(13) 0.0089(12) -0.0083(11) 0.0108(11) C8 0.0441(10) 0.0504(12) 0.0537(12) 0.0041(10) 0.0025(9) 0.0070(9) C9 0.0475(10) 0.0493(13) 0.0565(12) 0.0153(9) 0.0054(9) 0.0038(9) C10 0.0502(11) 0.0542(13) 0.0423(10) 0.0120(9) 0.0065(9) 0.0053(9) C11 0.0492(11) 0.0631(13) 0.0426(11) 0.0118(10) 0.0065(9) 0.0042(10) C12 0.0630(13) 0.0637(13) 0.0365(10) 0.0087(10) 0.0025(9) 0.0033(11) C13 0.0889(18) 0.0689(16) 0.0497(13) 0.0018(12) -0.0020(12) 0.0031(13) C14 0.119(2) 0.0693(17) 0.0533(14) -0.0079(12) 0.0013(15) 0.0089(16) C15 0.136(3) 0.079(2) 0.0431(13) -0.0029(13) 0.0014(15) 0.030(2) C16 0.0867(18) 0.101(2) 0.0458(13) 0.0148(13) 0.0150(12) 0.0355(17) C17 0.0611(13) 0.0738(16) 0.0363(11) 0.0139(10) 0.0055(9) 0.0147(12) C18 0.0505(12) 0.094(2) 0.0596(14) 0.0192(13) 0.0158(11) 0.0119(13) C19 0.0490(12) 0.0687(14) 0.0580(13) 0.0152(11) 0.0090(10) -0.0009(10) C20 0.0642(14) 0.0355(10) 0.0697(15) -0.0031(10) 0.0041(11) -0.0106(10) C21 0.0542(12) 0.0480(12) 0.0577(13) -0.0120(9) 0.0073(10) 0.0055(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 O2 1.4637(13) . ? P1 O1 1.5842(12) . ? P1 N1 1.6253(16) . ? P1 C9 1.827(2) . ? F1 C9 1.405(2) . ? O1 C2 1.472(2) . ? N1 C20 1.452(2) . ? N1 C1 1.472(2) . ? C1 C21 1.516(3) . ? C1 C2 1.553(2) . ? C2 C3 1.506(3) . ? C3 C8 1.382(3) . ? C3 C4 1.390(3) . ? C4 C5 1.380(3) . ? C5 C6 1.365(3) . ? C6 C7 1.385(3) . ? C7 C8 1.392(3) . ? C9 C10 1.495(3) . ? C10 C11 1.350(3) . ? C10 C19 1.412(3) . ? C11 C12 1.439(3) . ? C12 C17 1.404(3) . ? C12 C13 1.407(4) . ? C13 C14 1.358(4) . ? C14 C15 1.398(4) . ? C15 C16 1.354(5) . ? C16 C17 1.443(4) . ? C17 C18 1.398(4) . ? C18 C19 1.372(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O1 118.37(7) . . ? O2 P1 N1 117.34(8) . . ? O1 P1 N1 96.75(7) . . ? O2 P1 C9 107.49(9) . . ? O1 P1 C9 103.89(8) . . ? N1 P1 C9 112.13(9) . . ? C2 O1 P1 112.96(11) . . ? C20 N1 C1 120.36(16) . . ? C20 N1 P1 122.80(14) . . ? C1 N1 P1 111.71(12) . . ? N1 C1 C21 112.71(16) . . ? N1 C1 C2 102.91(15) . . ? C21 C1 C2 114.93(18) . . ? O1 C2 C3 109.66(14) . . ? O1 C2 C1 105.20(16) . . ? C3 C2 C1 116.63(18) . . ? C8 C3 C4 118.61(18) . . ? C8 C3 C2 122.85(16) . . ? C4 C3 C2 118.54(16) . . ? C5 C4 C3 120.5(2) . . ? C6 C5 C4 121.1(2) . . ? C5 C6 C7 119.2(2) . . ? C6 C7 C8 120.3(2) . . ? C3 C8 C7 120.4(2) . . ? F1 C9 C10 111.14(17) . . ? F1 C9 P1 108.44(13) . . ? C10 C9 P1 112.31(13) . . ? C11 C10 C19 120.0(2) . . ? C11 C10 C9 120.67(19) . . ? C19 C10 C9 119.3(2) . . ? C10 C11 C12 121.2(2) . . ? C17 C12 C13 120.1(2) . . ? C17 C12 C11 118.1(2) . . ? C13 C12 C11 121.8(2) . . ? C14 C13 C12 120.2(3) . . ? C13 C14 C15 121.0(3) . . ? C16 C15 C14 120.5(3) . . ? C15 C16 C17 120.4(3) . . ? C18 C17 C12 119.6(2) . . ? C18 C17 C16 122.6(2) . . ? C12 C17 C16 117.8(3) . . ? C19 C18 C17 121.0(2) . . ? C18 C19 C10 120.1(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 O2 P1 O1 C2 -121.53(12) . . . . ? N1 P1 O1 C2 4.59(13) . . . . ? C9 P1 O1 C2 119.43(12) . . . . ? O2 P1 N1 C20 -61.64(19) . . . . ? O1 P1 N1 C20 171.50(16) . . . . ? C9 P1 N1 C20 63.49(19) . . . . ? O2 P1 N1 C1 143.72(13) . . . . ? O1 P1 N1 C1 16.86(14) . . . . ? C9 P1 N1 C1 -91.15(15) . . . . ? C20 N1 C1 C21 49.6(3) . . . . ? P1 N1 C1 C21 -155.02(14) . . . . ? C20 N1 C1 C2 174.02(18) . . . . ? P1 N1 C1 C2 -30.64(19) . . . . ? P1 O1 C2 C3 103.40(15) . . . . ? P1 O1 C2 C1 -22.77(18) . . . . ? N1 C1 C2 O1 31.82(19) . . . . ? C21 C1 C2 O1 154.73(14) . . . . ? N1 C1 C2 C3 -89.93(19) . . . . ? C21 C1 C2 C3 33.0(2) . . . . ? O1 C2 C3 C8 -24.4(3) . . . . ? C1 C2 C3 C8 95.0(2) . . . . ? O1 C2 C3 C4 155.25(18) . . . . ? C1 C2 C3 C4 -85.4(2) . . . . ? C8 C3 C4 C5 1.5(3) . . . . ? C2 C3 C4 C5 -178.1(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C5 C6 C7 C8 0.8(4) . . . . ? C4 C3 C8 C7 -1.4(3) . . . . ? C2 C3 C8 C7 178.2(2) . . . . ? C6 C7 C8 C3 0.3(4) . . . . ? O2 P1 C9 F1 -176.87(13) . . . . ? O1 P1 C9 F1 -50.63(14) . . . . ? N1 P1 C9 F1 52.74(16) . . . . ? O2 P1 C9 C10 -53.66(16) . . . . ? O1 P1 C9 C10 72.58(15) . . . . ? N1 P1 C9 C10 175.96(13) . . . . ? F1 C9 C10 C11 46.4(2) . . . . ? P1 C9 C10 C11 -75.3(2) . . . . ? F1 C9 C10 C19 -135.76(19) . . . . ? P1 C9 C10 C19 102.56(19) . . . . ? C19 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C12 177.61(18) . . . . ? C10 C11 C12 C17 1.5(3) . . . . ? C10 C11 C12 C13 -177.6(2) . . . . ? C17 C12 C13 C14 0.7(3) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? C12 C13 C14 C15 1.0(4) . . . . ? C13 C14 C15 C16 -1.6(4) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C13 C12 C17 C18 177.3(2) . . . . ? C11 C12 C17 C18 -1.8(3) . . . . ? C13 C12 C17 C16 -1.7(3) . . . . ? C11 C12 C17 C16 179.2(2) . . . . ? C15 C16 C17 C18 -177.9(2) . . . . ? C15 C16 C17 C12 1.1(3) . . . . ? C12 C17 C18 C19 0.9(3) . . . . ? C16 C17 C18 C19 179.9(2) . . . . ? C17 C18 C19 C10 0.4(3) . . . . ? C11 C10 C19 C18 -0.7(3) . . . . ? C9 C10 C19 C18 -178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.137 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.026 data_k9998a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 F N O2 P' _chemical_formula_weight 395.39 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 12.2726(2) _cell_length_b 24.9928(3) _cell_length_c 6.6447(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2038.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_T_max 0.9683 _exptl_absorpt_process_details 'multi-scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12421 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4608 _reflns_number_gt 3884 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.0028P] 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 SHELXL _refine_ls_extinction_coef 0.0044(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(8) _refine_ls_number_reflns 4608 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0796 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.002 _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 0.66735(3) 0.228459(17) 0.49080(6) 0.02013(10) Uani 1 1 d . . . F1 F 0.73135(8) 0.13770(4) 0.64825(15) 0.0325(2) Uani 1 1 d . . . O1 O 0.57766(8) 0.22834(5) 0.66280(15) 0.0208(2) Uani 1 1 d . . . O2 O 0.63785(9) 0.25017(5) 0.29319(16) 0.0262(3) Uani 1 1 d . . . N1 N 0.76055(10) 0.26017(6) 0.61906(18) 0.0217(3) Uani 1 1 d . . . C1 C 0.73608(12) 0.26068(7) 0.8354(2) 0.0214(3) Uani 1 1 d . . . H1A H 0.7633 0.2267 0.8971 0.026 Uiso 1 1 calc R . . C2 C 0.60951(12) 0.26058(6) 0.8397(2) 0.0199(3) Uani 1 1 d . . . H2B H 0.5849 0.2415 0.9641 0.024 Uiso 1 1 calc R . . C3 C 0.55422(12) 0.31454(7) 0.8320(2) 0.0222(3) Uani 1 1 d . . . C4 C 0.56004(14) 0.34829(7) 0.6637(3) 0.0295(4) Uani 1 1 d . . . H4A H 0.5992 0.3372 0.5477 0.035 Uiso 1 1 calc R . . C5 C 0.50913(15) 0.39758(8) 0.6658(3) 0.0350(4) Uani 1 1 d . . . H5A H 0.5141 0.4203 0.5516 0.042 Uiso 1 1 calc R . . C6 C 0.45055(14) 0.41412(8) 0.8339(3) 0.0334(4) Uani 1 1 d . . . H6A H 0.4153 0.4480 0.8344 0.040 Uiso 1 1 calc R . . C7 C 0.44390(14) 0.38108(7) 1.0002(3) 0.0333(4) Uani 1 1 d . . . H7A H 0.4040 0.3921 1.1154 0.040 Uiso 1 1 calc R . . C8 C 0.49577(12) 0.33175(7) 0.9981(3) 0.0270(4) Uani 1 1 d . . . H8A H 0.4911 0.3093 1.1132 0.032 Uiso 1 1 calc R . . C9 C 0.70481(14) 0.15848(7) 0.4571(2) 0.0252(4) Uani 1 1 d . . . H9A H 0.7712 0.1568 0.3701 0.030 Uiso 1 1 calc R . . C10 C 0.61620(13) 0.12590(7) 0.3598(3) 0.0242(4) Uani 1 1 d . . . C11 C 0.52569(13) 0.10944(7) 0.4688(2) 0.0236(3) Uani 1 1 d . . . H11A H 0.5198 0.1191 0.6066 0.028 Uiso 1 1 calc R . . C12 C 0.44337(14) 0.07907(7) 0.3806(3) 0.0247(4) Uani 1 1 d . . . C13 C 0.45265(15) 0.06642(7) 0.1756(3) 0.0294(4) Uani 1 1 d . . . H13A H 0.3969 0.0463 0.1116 0.035 Uiso 1 1 calc R . . C14 C 0.54233(15) 0.08304(8) 0.0657(3) 0.0323(4) Uani 1 1 d . . . H14A H 0.5475 0.0741 -0.0729 0.039 Uiso 1 1 calc R . . C15 C 0.62423(14) 0.11239(7) 0.1548(3) 0.0287(4) Uani 1 1 d . . . H15A H 0.6856 0.1234 0.0783 0.034 Uiso 1 1 calc R . . C16 C 0.34778(13) 0.06029(6) 0.5009(3) 0.0260(3) Uani 1 1 d . . . C17 C 0.30229(15) 0.01017(7) 0.4673(3) 0.0339(4) Uani 1 1 d . . . H17A H 0.3311 -0.0119 0.3637 0.041 Uiso 1 1 calc R . . C18 C 0.21611(16) -0.00820(8) 0.5815(3) 0.0389(5) Uani 1 1 d . . . H18A H 0.1869 -0.0428 0.5570 0.047 Uiso 1 1 calc R . . C19 C 0.17190(16) 0.02376(8) 0.7322(3) 0.0367(5) Uani 1 1 d . . . H19A H 0.1122 0.0113 0.8103 0.044 Uiso 1 1 calc R . . C20 C 0.21550(16) 0.07355(9) 0.7670(3) 0.0385(5) Uani 1 1 d . . . H20A H 0.1859 0.0955 0.8701 0.046 Uiso 1 1 calc R . . C21 C 0.30295(14) 0.09206(8) 0.6520(3) 0.0330(4) Uani 1 1 d . . . H21A H 0.3321 0.1266 0.6770 0.040 Uiso 1 1 calc R . . C22 C 0.87329(12) 0.26244(7) 0.5482(2) 0.0282(4) Uani 1 1 d . . . H22A H 0.9078 0.2953 0.5977 0.042 Uiso 1 1 calc R . . H22B H 0.8743 0.2623 0.4008 0.042 Uiso 1 1 calc R . . H22C H 0.9133 0.2313 0.5988 0.042 Uiso 1 1 calc R . . C23 C 0.78801(14) 0.30781(7) 0.9428(2) 0.0284(4) Uani 1 1 d . . . H23A H 0.8671 0.3026 0.9491 0.043 Uiso 1 1 calc R . . H23B H 0.7586 0.3104 1.0796 0.043 Uiso 1 1 calc R . . H23C H 0.7719 0.3408 0.8690 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01837(18) 0.0242(2) 0.01778(18) 0.00067(19) 0.00067(17) 0.00056(17) F1 0.0373(6) 0.0290(6) 0.0313(5) 0.0029(5) -0.0107(5) 0.0049(4) O1 0.0182(5) 0.0267(6) 0.0174(5) -0.0039(5) -0.0008(4) -0.0024(5) O2 0.0298(6) 0.0310(7) 0.0179(5) 0.0017(5) -0.0012(5) 0.0026(5) N1 0.0163(6) 0.0299(8) 0.0189(6) -0.0005(6) 0.0014(5) -0.0018(6) C1 0.0191(7) 0.0262(9) 0.0187(7) 0.0017(7) -0.0026(6) -0.0018(7) C2 0.0203(7) 0.0253(9) 0.0140(7) -0.0021(7) -0.0004(6) -0.0022(7) C3 0.0188(7) 0.0249(9) 0.0228(8) -0.0013(7) -0.0013(7) -0.0026(7) C4 0.0315(9) 0.0304(10) 0.0266(9) 0.0046(8) 0.0069(8) 0.0031(8) C5 0.0375(10) 0.0325(11) 0.0351(10) 0.0079(9) 0.0048(9) 0.0044(8) C6 0.0308(9) 0.0293(10) 0.0402(10) -0.0031(9) -0.0001(9) 0.0074(8) C7 0.0292(8) 0.0414(11) 0.0293(9) -0.0071(9) 0.0040(9) 0.0059(8) C8 0.0246(8) 0.0333(10) 0.0230(7) -0.0003(8) -0.0003(8) 0.0004(7) C9 0.0239(8) 0.0287(9) 0.0230(8) 0.0019(7) 0.0004(7) 0.0040(7) C10 0.0281(9) 0.0209(9) 0.0236(8) 0.0002(7) -0.0012(8) 0.0038(7) C11 0.0287(8) 0.0208(8) 0.0212(8) -0.0006(7) -0.0008(7) 0.0045(7) C12 0.0279(9) 0.0189(9) 0.0274(8) 0.0002(7) -0.0025(7) 0.0045(7) C13 0.0361(10) 0.0239(9) 0.0283(9) -0.0011(8) -0.0091(8) 0.0019(8) C14 0.0443(11) 0.0308(10) 0.0219(8) 0.0000(7) -0.0037(8) 0.0026(9) C15 0.0350(9) 0.0264(9) 0.0246(8) 0.0025(8) 0.0010(8) 0.0043(8) C16 0.0271(8) 0.0208(8) 0.0301(8) -0.0001(8) -0.0043(8) 0.0020(7) C17 0.0347(10) 0.0232(9) 0.0438(11) -0.0056(8) -0.0008(9) 0.0025(8) C18 0.0340(10) 0.0264(10) 0.0563(12) -0.0013(9) -0.0006(10) -0.0035(8) C19 0.0279(9) 0.0380(11) 0.0441(11) 0.0076(9) -0.0002(9) -0.0042(9) C20 0.0330(10) 0.0416(12) 0.0409(10) -0.0067(9) 0.0056(9) -0.0031(9) C21 0.0325(9) 0.0289(10) 0.0375(10) -0.0095(9) 0.0032(8) -0.0046(8) C22 0.0186(7) 0.0337(10) 0.0322(9) 0.0026(8) 0.0034(7) -0.0002(7) C23 0.0255(8) 0.0315(10) 0.0282(9) -0.0022(7) -0.0033(7) -0.0072(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 P1 O2 1.4662(11) . ? P1 O1 1.5867(11) . ? P1 N1 1.6317(13) . ? P1 C9 1.8223(18) . ? F1 C9 1.4101(18) . ? O1 C2 1.4780(18) . ? N1 C22 1.4626(19) . ? N1 C1 1.4686(19) . ? C1 C23 1.518(2) . ? C1 C2 1.554(2) . ? C2 C3 1.511(2) . ? C3 C8 1.385(2) . ? C3 C4 1.402(2) . ? C4 C5 1.381(3) . ? C5 C6 1.391(3) . ? C6 C7 1.382(3) . ? C7 C8 1.387(2) . ? C9 C10 1.505(2) . ? C10 C11 1.388(2) . ? C10 C15 1.407(2) . ? C11 C12 1.393(2) . ? C12 C13 1.403(2) . ? C12 C16 1.495(2) . ? C13 C14 1.384(3) . ? C14 C15 1.378(2) . ? C16 C17 1.389(2) . ? C16 C21 1.394(2) . ? C17 C18 1.380(3) . ? C18 C19 1.391(3) . ? C19 C20 1.374(3) . ? C20 C21 1.396(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 O2 P1 O1 118.33(6) . . ? O2 P1 N1 117.46(7) . . ? O1 P1 N1 96.37(6) . . ? O2 P1 C9 107.91(7) . . ? O1 P1 C9 105.17(7) . . ? N1 P1 C9 110.70(7) . . ? C2 O1 P1 112.86(9) . . ? C22 N1 C1 120.53(12) . . ? C22 N1 P1 120.93(11) . . ? C1 N1 P1 111.84(10) . . ? N1 C1 C23 112.41(13) . . ? N1 C1 C2 102.86(12) . . ? C23 C1 C2 114.35(14) . . ? O1 C2 C3 109.92(12) . . ? O1 C2 C1 104.50(12) . . ? C3 C2 C1 116.56(13) . . ? C8 C3 C4 118.36(16) . . ? C8 C3 C2 118.86(15) . . ? C4 C3 C2 122.78(15) . . ? C5 C4 C3 120.36(16) . . ? C4 C5 C6 120.45(18) . . ? C7 C6 C5 119.66(17) . . ? C6 C7 C8 119.74(17) . . ? C3 C8 C7 121.42(17) . . ? F1 C9 C10 110.78(14) . . ? F1 C9 P1 107.53(10) . . ? C10 C9 P1 112.94(11) . . ? C11 C10 C15 119.35(16) . . ? C11 C10 C9 120.95(15) . . ? C15 C10 C9 119.70(15) . . ? C10 C11 C12 121.48(15) . . ? C11 C12 C13 118.19(16) . . ? C11 C12 C16 121.02(15) . . ? C13 C12 C16 120.79(16) . . ? C14 C13 C12 120.59(17) . . ? C15 C14 C13 120.88(16) . . ? C14 C15 C10 119.50(17) . . ? C17 C16 C21 118.08(17) . . ? C17 C16 C12 120.84(16) . . ? C21 C16 C12 121.07(15) . . ? C18 C17 C16 121.31(17) . . ? C17 C18 C19 120.22(18) . . ? C20 C19 C18 119.29(19) . . ? C19 C20 C21 120.48(18) . . ? C16 C21 C20 120.60(17) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.184 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.038 data_k9962 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 F N O2 P' _chemical_formula_weight 319.30 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9593(7) _cell_length_b 6.5312(3) _cell_length_c 12.2863(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.346(3) _cell_angle_gamma 90.00 _cell_volume 798.51(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9369 _exptl_absorpt_correction_T_max 0.9456 _exptl_absorpt_process_details 'Denzo-SMN' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10240 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3541 _reflns_number_gt 3235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'Bruker SHELXTL V5.1' _computing_structure_refinement 'Bruker SHELXTL V5.1' _computing_molecular_graphics 'Bruker SHELXTL V5.1' _computing_publication_material 'Bruker SHELXTL V5.1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0446P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_ls_number_reflns 3541 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 2.184 _refine_ls_shift/su_mean 0.011 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 0.30745(4) 0.29173(6) 0.29592(3) 0.02272(12) Uani 1 1 d . . . F1 F 0.43760(12) 0.4813(2) 0.45536(10) 0.0464(3) Uani 1 1 d . . . O1 O 0.23273(14) 0.1019(2) 0.27571(12) 0.0309(3) Uani 1 1 d . . . O2 O 0.23338(13) 0.50008(18) 0.26917(10) 0.0239(3) Uani 1 1 d . . . N1 N 0.43941(15) 0.3344(2) 0.22243(13) 0.0251(3) Uani 1 1 d . . . C1 C 0.45534(19) 0.5562(3) 0.20491(16) 0.0262(4) Uani 1 1 d . . . H1A H 0.5016 0.6168 0.2711 0.031 Uiso 1 1 calc R . . C2 C 0.30899(17) 0.6366(3) 0.19693(14) 0.0234(4) Uani 1 1 d . . . H2A H 0.3077 0.7785 0.2275 0.028 Uiso 1 1 calc R . . C3 C 0.35807(17) 0.3030(4) 0.44020(14) 0.0288(4) Uani 1 1 d . . . H3A H 0.4160 0.1814 0.4576 0.035 Uiso 1 1 calc R . . C4 C 0.24540(16) 0.3047(3) 0.51768(13) 0.0266(3) Uani 1 1 d . . . C5 C 0.16521(19) 0.4778(3) 0.52730(15) 0.0310(4) Uani 1 1 d . . . H5A H 0.1828 0.5970 0.4859 0.037 Uiso 1 1 calc R . . C6 C 0.0592(2) 0.4759(4) 0.59775(17) 0.0375(5) Uani 1 1 d . . . H6A H 0.0047 0.5942 0.6050 0.045 Uiso 1 1 calc R . . C7 C 0.0333(2) 0.3017(4) 0.65706(16) 0.0395(4) Uani 1 1 d . . . H7A H -0.0396 0.3005 0.7046 0.047 Uiso 1 1 calc R . . C8 C 0.1115(2) 0.1305(4) 0.64822(18) 0.0422(5) Uani 1 1 d . . . H8A H 0.0927 0.0115 0.6894 0.051 Uiso 1 1 calc R . . C9 C 0.2194(2) 0.1310(3) 0.57841(16) 0.0343(4) Uani 1 1 d . . . H9A H 0.2745 0.0130 0.5727 0.041 Uiso 1 1 calc R . . C10 C 0.23928(17) 0.6395(3) 0.08594(14) 0.0241(4) Uani 1 1 d . . . C11 C 0.22667(17) 0.4653(3) 0.01991(15) 0.0270(4) Uani 1 1 d . . . H11A H 0.2639 0.3388 0.0446 0.032 Uiso 1 1 calc R . . C12 C 0.16014(18) 0.4762(3) -0.08122(15) 0.0292(4) Uani 1 1 d . . . H12A H 0.1532 0.3576 -0.1259 0.035 Uiso 1 1 calc R . . C13 C 0.10357(19) 0.6593(3) -0.11779(16) 0.0298(4) Uani 1 1 d . . . H13A H 0.0567 0.6656 -0.1866 0.036 Uiso 1 1 calc R . . C14 C 0.11590(19) 0.8328(3) -0.05324(16) 0.0300(4) Uani 1 1 d . . . H14A H 0.0777 0.9586 -0.0780 0.036 Uiso 1 1 calc R . . C15 C 0.18447(17) 0.8232(3) 0.04814(15) 0.0268(4) Uani 1 1 d . . . H15A H 0.1937 0.9431 0.0916 0.032 Uiso 1 1 calc R . . C16 C 0.53708(19) 0.6067(3) 0.10625(17) 0.0336(4) Uani 1 1 d . . . H16A H 0.6303 0.5626 0.1199 0.050 Uiso 1 1 calc R . . H16B H 0.5348 0.7547 0.0932 0.050 Uiso 1 1 calc R . . H16C H 0.4987 0.5351 0.0421 0.050 Uiso 1 1 calc R . . C17 C 0.5594(2) 0.2064(3) 0.23279(18) 0.0340(4) Uani 1 1 d . . . H17A H 0.6037 0.2028 0.1630 0.051 Uiso 1 1 calc R . . H17B H 0.5338 0.0671 0.2533 0.051 Uiso 1 1 calc R . . H17C H 0.6213 0.2632 0.2890 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0231(2) 0.0233(2) 0.0218(2) -0.0019(2) 0.00048(15) 0.00094(19) F1 0.0377(6) 0.0710(9) 0.0305(6) -0.0121(6) -0.0005(5) -0.0235(7) O1 0.0345(8) 0.0260(7) 0.0325(8) -0.0034(5) 0.0038(6) -0.0026(6) O2 0.0235(6) 0.0262(7) 0.0221(7) 0.0018(5) 0.0036(5) 0.0018(5) N1 0.0231(7) 0.0261(9) 0.0263(8) -0.0008(6) 0.0038(6) 0.0034(5) C1 0.0252(9) 0.0282(9) 0.0251(9) -0.0029(7) 0.0009(7) -0.0018(7) C2 0.0264(8) 0.0234(8) 0.0205(9) -0.0006(7) 0.0009(7) -0.0004(7) C3 0.0250(8) 0.0371(9) 0.0239(8) 0.0019(9) -0.0041(6) 0.0010(9) C4 0.0254(8) 0.0356(9) 0.0182(8) 0.0001(8) -0.0056(6) -0.0002(9) C5 0.0323(10) 0.0371(11) 0.0232(9) -0.0018(8) -0.0022(7) 0.0017(8) C6 0.0310(10) 0.0558(13) 0.0256(10) -0.0091(10) -0.0015(8) 0.0034(10) C7 0.0344(9) 0.0611(13) 0.0229(9) -0.0092(11) 0.0011(7) -0.0073(12) C8 0.0542(13) 0.0504(13) 0.0219(10) 0.0028(9) 0.0004(9) -0.0176(11) C9 0.0414(11) 0.0364(10) 0.0245(10) 0.0022(8) -0.0046(8) -0.0005(9) C10 0.0230(8) 0.0267(9) 0.0227(9) -0.0007(7) 0.0028(7) -0.0004(7) C11 0.0275(9) 0.0272(9) 0.0265(9) -0.0020(7) 0.0027(7) -0.0006(7) C12 0.0289(9) 0.0331(10) 0.0256(9) -0.0045(8) 0.0023(7) -0.0042(8) C13 0.0270(9) 0.0414(11) 0.0209(10) 0.0019(8) 0.0004(8) -0.0023(8) C14 0.0276(9) 0.0332(11) 0.0292(10) 0.0039(8) 0.0012(7) 0.0025(7) C15 0.0277(8) 0.0273(10) 0.0256(9) -0.0003(7) 0.0025(7) 0.0006(7) C16 0.0300(10) 0.0377(12) 0.0334(11) 0.0010(8) 0.0066(8) -0.0032(8) C17 0.0268(10) 0.0338(10) 0.0413(12) -0.0035(8) 0.0011(9) 0.0082(7) _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 1.4618(14) . ? P1 O2 1.5761(13) . ? P1 N1 1.6485(15) . ? P1 C3 1.8245(18) . ? F1 C3 1.416(2) . ? O2 C2 1.485(2) . ? N1 C17 1.460(2) . ? N1 C1 1.474(2) . ? C1 C16 1.524(3) . ? C1 C2 1.549(3) . ? C2 C10 1.505(2) . ? C3 C4 1.501(2) . ? C4 C9 1.388(3) . ? C4 C5 1.392(3) . ? C5 C6 1.393(3) . ? C6 C7 1.381(3) . ? C7 C8 1.369(4) . ? C8 C9 1.402(3) . ? C10 C15 1.390(2) . ? C10 C11 1.400(2) . ? C11 C12 1.386(3) . ? C12 C13 1.389(3) . ? C13 C14 1.386(3) . ? C14 C15 1.397(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 O2 117.78(6) . . ? O1 P1 N1 117.53(7) . . ? O2 P1 N1 96.69(7) . . ? O1 P1 C3 108.52(9) . . ? O2 P1 C3 106.03(9) . . ? N1 P1 C3 109.30(8) . . ? C2 O2 P1 113.50(10) . . ? C17 N1 C1 118.89(16) . . ? C17 N1 P1 121.56(13) . . ? C1 N1 P1 109.83(11) . . ? N1 C1 C16 113.13(15) . . ? N1 C1 C2 103.64(15) . . ? C16 C1 C2 114.11(16) . . ? O2 C2 C10 108.83(14) . . ? O2 C2 C1 104.92(14) . . ? C10 C2 C1 117.37(15) . . ? F1 C3 C4 109.81(16) . . ? F1 C3 P1 106.96(12) . . ? C4 C3 P1 115.62(12) . . ? C9 C4 C5 119.87(17) . . ? C9 C4 C3 119.68(18) . . ? C5 C4 C3 120.43(18) . . ? C4 C5 C6 119.86(19) . . ? C7 C6 C5 119.9(2) . . ? C8 C7 C6 120.78(18) . . ? C7 C8 C9 120.0(2) . . ? C4 C9 C8 119.66(19) . . ? C15 C10 C11 118.88(16) . . ? C15 C10 C2 118.29(16) . . ? C11 C10 C2 122.83(16) . . ? C12 C11 C10 120.39(17) . . ? C11 C12 C13 120.48(17) . . ? C14 C13 C12 119.59(17) . . ? C13 C14 C15 120.12(17) . . ? C10 C15 C14 120.53(16) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.283 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.044