data_sdr13 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 F3 N O3' _chemical_formula_weight 309.33 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.8599(9) _cell_length_b 20.656(2) _cell_length_c 9.0612(9) _cell_angle_alpha 90.00 _cell_angle_beta 114.216(2) _cell_angle_gamma 90.00 _cell_volume 1512.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description mfp _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 frames' _diffrn_standards_interval_count 'initial 50 frames recollected' _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1.0' _diffrn_reflns_number 15886 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3678 _reflns_number_gt 2805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART/SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.9311P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3678 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 N1 N 0.02702(15) 0.08164(6) -0.17550(15) 0.0169(2) Uani 1 1 d . . . O1 O -0.57739(14) 0.20581(6) -0.20269(15) 0.0329(3) Uani 1 1 d . . . C1 C 0.1407(2) 0.07220(8) -0.25911(19) 0.0233(3) Uani 1 1 d . . . C2 C 0.0517(2) 0.08950(8) -0.4363(2) 0.0280(3) Uani 1 1 d . . . C3 C -0.0037(2) 0.15979(8) -0.45100(19) 0.0251(3) Uani 1 1 d . . . C4 C -0.11798(19) 0.17049(7) -0.36459(18) 0.0209(3) Uani 1 1 d . . . C5 C -0.04612(17) 0.14900(6) -0.18618(16) 0.0164(3) Uani 1 1 d . . . C6 C -0.18779(17) 0.14092(7) -0.12791(17) 0.0179(3) Uani 1 1 d . . . C7 C -0.2910(2) 0.20319(8) -0.1521(2) 0.0249(3) Uani 1 1 d . . . C8 C -0.43722(19) 0.19187(7) -0.1091(2) 0.0243(3) Uani 1 1 d . . . C9 C -0.3966(2) 0.16266(9) 0.0547(2) 0.0295(4) Uani 1 1 d . . . C10 C -0.2837(2) 0.10343(8) 0.0835(2) 0.0265(3) Uani 1 1 d . . . C11 C -0.13293(19) 0.11794(8) 0.04710(18) 0.0222(3) Uani 1 1 d . . . C12 C 0.09069(18) 0.19463(7) -0.07937(19) 0.0207(3) Uani 1 1 d . . . H1 H 0.085(2) 0.0707(9) -0.071(2) 0.026(5) Uiso 1 1 d . . . H2 H -0.057(2) 0.0508(10) -0.219(2) 0.030(5) Uiso 1 1 d . . . H1A H 0.238(2) 0.0993(9) -0.204(2) 0.026(5) Uiso 1 1 d . . . H1B H 0.172(2) 0.0268(9) -0.244(2) 0.026(4) Uiso 1 1 d . . . H2A H 0.126(2) 0.0803(9) -0.488(2) 0.035(5) Uiso 1 1 d . . . H2B H -0.043(2) 0.0615(10) -0.487(2) 0.031(5) Uiso 1 1 d . . . H3A H -0.060(2) 0.1726(9) -0.563(2) 0.026(4) Uiso 1 1 d . . . H3B H 0.094(2) 0.1877(9) -0.405(2) 0.028(5) Uiso 1 1 d . . . H4A H -0.144(2) 0.2153(9) -0.366(2) 0.020(4) Uiso 1 1 d . . . H4B H -0.220(2) 0.1469(9) -0.421(2) 0.031(5) Uiso 1 1 d . . . H6A H -0.259(2) 0.1083(8) -0.196(2) 0.019(4) Uiso 1 1 d . . . H7A H -0.222(2) 0.2372(10) -0.078(2) 0.032(5) Uiso 1 1 d . . . H7B H -0.333(2) 0.2178(9) -0.261(2) 0.032(5) Uiso 1 1 d . . . H9A H -0.497(3) 0.1518(10) 0.066(3) 0.044(6) Uiso 1 1 d . . . H9B H -0.336(2) 0.1960(10) 0.137(2) 0.032(5) Uiso 1 1 d . . . H10A H -0.348(2) 0.0668(9) 0.012(2) 0.028(5) Uiso 1 1 d . . . H10B H -0.247(2) 0.0878(9) 0.196(2) 0.032(5) Uiso 1 1 d . . . H11A H -0.066(2) 0.0791(9) 0.068(2) 0.025(4) Uiso 1 1 d . . . H11B H -0.062(2) 0.1516(9) 0.122(2) 0.030(5) Uiso 1 1 d . . . H12A H 0.175(2) 0.1997(9) -0.123(2) 0.025(4) Uiso 1 1 d . . . H12B H 0.143(2) 0.1780(9) 0.030(2) 0.025(4) Uiso 1 1 d . . . H12C H 0.039(2) 0.2358(10) -0.078(2) 0.032(5) Uiso 1 1 d . . . C13 C 0.28094(18) 0.04202(7) 0.26219(18) 0.0211(3) Uani 1 1 d . . . C14 C 0.4219(2) 0.08541(8) 0.3775(2) 0.0302(4) Uani 1 1 d . . . O3 O 0.20398(14) 0.01106(6) 0.32578(14) 0.0295(3) Uani 1 1 d . . . O2 O 0.26181(14) 0.04496(6) 0.11896(13) 0.0330(3) Uani 1 1 d . . . F1 F 0.3820(2) 0.14771(6) 0.34634(18) 0.0747(5) Uani 1 1 d . . . F2 F 0.56226(14) 0.07642(7) 0.35846(14) 0.0560(4) Uani 1 1 d . . . F3 F 0.45843(13) 0.07593(6) 0.53325(12) 0.0410(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 N1 0.0165(6) 0.0152(6) 0.0179(6) -0.0008(5) 0.0060(5) -0.0007(5) O1 0.0202(6) 0.0357(7) 0.0409(7) -0.0006(5) 0.0107(5) 0.0044(5) C1 0.0249(8) 0.0199(7) 0.0297(8) 0.0000(6) 0.0159(7) 0.0019(6) C2 0.0379(9) 0.0252(8) 0.0266(8) -0.0020(6) 0.0191(7) -0.0013(7) C3 0.0302(8) 0.0241(8) 0.0216(7) 0.0028(6) 0.0111(6) -0.0027(7) C4 0.0202(7) 0.0196(7) 0.0201(7) 0.0024(6) 0.0053(6) -0.0004(6) C5 0.0155(6) 0.0132(6) 0.0185(6) 0.0000(5) 0.0050(5) 0.0008(5) C6 0.0147(6) 0.0170(7) 0.0200(7) 0.0001(5) 0.0053(5) -0.0003(5) C7 0.0221(8) 0.0218(8) 0.0316(8) 0.0065(6) 0.0119(7) 0.0051(6) C8 0.0224(7) 0.0176(7) 0.0343(8) -0.0026(6) 0.0129(7) 0.0021(6) C9 0.0291(9) 0.0294(9) 0.0368(9) 0.0029(7) 0.0202(7) 0.0063(7) C10 0.0296(8) 0.0247(8) 0.0308(8) 0.0042(7) 0.0181(7) 0.0043(7) C11 0.0216(7) 0.0224(8) 0.0233(7) 0.0032(6) 0.0099(6) 0.0043(6) C12 0.0181(7) 0.0184(7) 0.0234(7) -0.0033(6) 0.0064(6) -0.0024(6) C13 0.0163(7) 0.0198(7) 0.0227(7) -0.0029(6) 0.0036(6) 0.0034(5) C14 0.0296(9) 0.0281(9) 0.0280(8) -0.0011(7) 0.0069(7) -0.0089(7) O3 0.0276(6) 0.0275(6) 0.0344(6) -0.0089(5) 0.0137(5) -0.0098(5) O2 0.0269(6) 0.0452(7) 0.0207(6) -0.0006(5) 0.0035(5) 0.0069(5) F1 0.0932(11) 0.0206(6) 0.0763(10) -0.0038(6) 0.0004(8) -0.0121(6) F2 0.0290(6) 0.0958(11) 0.0431(7) -0.0081(6) 0.0146(5) -0.0269(6) F3 0.0347(6) 0.0581(7) 0.0236(5) -0.0117(5) 0.0054(4) -0.0142(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 N1 C1 1.5008(18) . ? N1 C5 1.5212(17) . ? O1 C8 1.2168(19) . ? C1 C2 1.513(2) . ? C2 C3 1.521(2) . ? C3 C4 1.529(2) . ? C4 C5 1.5399(19) . ? C5 C12 1.5271(19) . ? C5 C6 1.5575(19) . ? C6 C11 1.531(2) . ? C6 C7 1.541(2) . ? C7 C8 1.516(2) . ? C8 C9 1.502(2) . ? C9 C10 1.534(2) . ? C10 C11 1.531(2) . ? C13 O3 1.2362(19) . ? C13 O2 1.2396(19) . ? C13 C14 1.544(2) . ? C14 F3 1.3264(19) . ? C14 F1 1.334(2) . ? C14 F2 1.337(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 C1 N1 C5 116.31(11) . . ? N1 C1 C2 109.86(13) . . ? C1 C2 C3 109.09(13) . . ? C2 C3 C4 110.56(13) . . ? C3 C4 C5 114.87(12) . . ? N1 C5 C12 108.52(11) . . ? N1 C5 C4 108.20(11) . . ? C12 C5 C4 111.49(12) . . ? N1 C5 C6 105.18(11) . . ? C12 C5 C6 113.07(12) . . ? C4 C5 C6 110.07(11) . . ? C11 C6 C7 108.90(12) . . ? C11 C6 C5 115.26(11) . . ? C7 C6 C5 112.10(12) . . ? C8 C7 C6 110.76(12) . . ? O1 C8 C9 123.09(14) . . ? O1 C8 C7 121.29(15) . . ? C9 C8 C7 115.62(13) . . ? C8 C9 C10 111.32(13) . . ? C11 C10 C9 111.92(13) . . ? C10 C11 C6 110.45(13) . . ? O3 C13 O2 130.44(15) . . ? O3 C13 C14 115.62(13) . . ? O2 C13 C14 113.92(14) . . ? F3 C14 F1 107.20(15) . . ? F3 C14 F2 106.44(14) . . ? F1 C14 F2 106.65(15) . . ? F3 C14 C13 114.26(13) . . ? F1 C14 C13 110.24(14) . . ? F2 C14 C13 111.65(14) . . ? 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 -57.18(17) . . . . ? N1 C1 C2 C3 59.55(17) . . . . ? C1 C2 C3 C4 -58.82(18) . . . . ? C2 C3 C4 C5 54.43(18) . . . . ? C1 N1 C5 C12 -71.96(15) . . . . ? C1 N1 C5 C4 49.17(15) . . . . ? C1 N1 C5 C6 166.77(12) . . . . ? C3 C4 C5 N1 -47.23(16) . . . . ? C3 C4 C5 C12 72.03(16) . . . . ? C3 C4 C5 C6 -161.66(12) . . . . ? N1 C5 C6 C11 62.18(15) . . . . ? C12 C5 C6 C11 -56.06(16) . . . . ? C4 C5 C6 C11 178.52(12) . . . . ? N1 C5 C6 C7 -172.49(12) . . . . ? C12 C5 C6 C7 69.26(15) . . . . ? C4 C5 C6 C7 -56.16(16) . . . . ? C11 C6 C7 C8 -56.57(17) . . . . ? C5 C6 C7 C8 174.69(12) . . . . ? C6 C7 C8 O1 -127.74(16) . . . . ? C6 C7 C8 C9 52.21(18) . . . . ? O1 C8 C9 C10 131.49(16) . . . . ? C7 C8 C9 C10 -48.5(2) . . . . ? C8 C9 C10 C11 50.43(19) . . . . ? C9 C10 C11 C6 -57.91(18) . . . . ? C7 C6 C11 C10 60.35(16) . . . . ? C5 C6 C11 C10 -172.70(12) . . . . ? O3 C13 C14 F3 10.1(2) . . . . ? O2 C13 C14 F3 -171.12(14) . . . . ? O3 C13 C14 F1 -110.71(17) . . . . ? O2 C13 C14 F1 68.10(19) . . . . ? O3 C13 C14 F2 130.93(15) . . . . ? O2 C13 C14 F2 -50.26(19) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.472 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.046