data_3l34 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(rac)-1' _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 F3 N3 O2' _chemical_formula_sum 'C16 H12 F3 N3 O2' _chemical_formula_weight 335.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.9441(5) _cell_length_b 7.5494(3) _cell_length_c 14.9398(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.557(2) _cell_angle_gamma 90.00 _cell_volume 1515.09(10) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 8110 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 34.85 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.815 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(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 43004 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 34.95 _reflns_number_total 6536 _reflns_number_gt 5065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.3500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6536 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.39092(7) 0.14775(13) 0.51093(7) 0.02436(18) Uani 1 1 d . . . H1A H 0.4549 0.1717 0.4978 0.037 Uiso 1 1 calc R . . H1B H 0.3769 0.0205 0.5049 0.037 Uiso 1 1 calc R . . H1C H 0.3939 0.1860 0.5743 0.037 Uiso 1 1 calc R . . O2 O 0.31345(5) 0.24303(9) 0.44611(4) 0.01895(12) Uani 1 1 d . . . C3 C 0.22593(6) 0.28050(11) 0.47194(5) 0.01550(14) Uani 1 1 d . . . C4 C 0.24501(7) 0.35566(11) 0.57157(6) 0.01731(15) Uani 1 1 d . . . O4 O 0.20575(6) 0.29901(10) 0.62840(5) 0.02661(15) Uani 1 1 d . . . N5 N 0.30868(6) 0.50251(10) 0.59417(5) 0.01709(13) Uani 1 1 d . . . N6 N 0.35860(6) 0.57497(11) 0.53368(5) 0.02052(14) Uani 1 1 d . . . N7 N 0.40932(6) 0.70807(11) 0.57359(6) 0.02254(15) Uani 1 1 d . . . C8 C 0.39487(7) 0.73088(12) 0.66160(6) 0.01968(16) Uani 1 1 d . . . C9 C 0.43286(8) 0.86086(13) 0.72861(7) 0.02688(19) Uani 1 1 d . . . H9A H 0.4771 0.9501 0.7190 0.032 Uiso 1 1 calc R . . C10 C 0.40275(9) 0.85283(14) 0.80944(7) 0.0298(2) Uani 1 1 d . . . H10A H 0.4263 0.9392 0.8564 0.036 Uiso 1 1 calc R . . C11 C 0.33791(9) 0.71939(15) 0.82353(7) 0.0289(2) Uani 1 1 d . . . H11A H 0.3192 0.7183 0.8802 0.035 Uiso 1 1 calc R . . C12 C 0.30020(8) 0.58928(13) 0.75797(6) 0.02400(18) Uani 1 1 d . . . H12A H 0.2568 0.4990 0.7680 0.029 Uiso 1 1 calc R . . C13 C 0.33037(7) 0.59984(11) 0.67609(5) 0.01729(14) Uani 1 1 d . . . C14 C 0.16536(6) 0.41298(11) 0.40212(5) 0.01555(14) Uani 1 1 d . . . C15 C 0.09641(7) 0.52497(13) 0.42603(7) 0.02215(17) Uani 1 1 d . . . H15A H 0.0873 0.5202 0.4868 0.027 Uiso 1 1 calc R . . C16 C 0.04112(8) 0.64349(14) 0.36115(7) 0.02626(19) Uani 1 1 d . . . H16A H -0.0055 0.7199 0.3777 0.032 Uiso 1 1 calc R . . C17 C 0.05388(8) 0.65040(14) 0.27211(7) 0.02556(18) Uani 1 1 d . . . H17A H 0.0164 0.7319 0.2279 0.031 Uiso 1 1 calc R . . C18 C 0.12161(8) 0.53775(13) 0.24792(6) 0.02369(18) Uani 1 1 d . . . H18A H 0.1297 0.5414 0.1868 0.028 Uiso 1 1 calc R . . C19 C 0.17764(7) 0.41960(12) 0.31265(6) 0.01894(15) Uani 1 1 d . . . H19A H 0.2242 0.3435 0.2959 0.023 Uiso 1 1 calc R . . C20 C 0.16435(7) 0.10696(12) 0.46670(6) 0.02035(16) Uani 1 1 d . . . F21 F 0.15342(5) 0.03167(8) 0.38341(4) 0.02783(14) Uani 1 1 d . . . F22 F 0.07325(5) 0.13531(9) 0.47670(5) 0.02741(13) Uani 1 1 d . . . F23 F 0.20874(5) -0.01348(8) 0.53049(5) 0.02942(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0223(4) 0.0216(4) 0.0289(4) 0.0047(3) 0.0063(3) 0.0050(3) O2 0.0183(3) 0.0209(3) 0.0195(3) 0.0019(2) 0.0083(2) 0.0033(2) C3 0.0171(3) 0.0154(3) 0.0153(3) -0.0009(2) 0.0066(3) -0.0016(3) C4 0.0200(4) 0.0172(3) 0.0157(3) -0.0001(3) 0.0065(3) -0.0032(3) O4 0.0343(4) 0.0296(4) 0.0196(3) -0.0020(3) 0.0136(3) -0.0126(3) N5 0.0216(3) 0.0164(3) 0.0142(3) 0.0001(2) 0.0065(2) -0.0041(2) N6 0.0263(4) 0.0193(3) 0.0177(3) 0.0021(2) 0.0090(3) -0.0048(3) N7 0.0268(4) 0.0194(3) 0.0214(3) 0.0022(3) 0.0063(3) -0.0058(3) C8 0.0216(4) 0.0165(3) 0.0187(3) 0.0014(3) 0.0013(3) -0.0016(3) C9 0.0299(5) 0.0202(4) 0.0252(4) -0.0023(3) -0.0017(3) -0.0045(3) C10 0.0358(5) 0.0249(4) 0.0233(4) -0.0064(3) -0.0018(4) -0.0004(4) C11 0.0386(6) 0.0293(5) 0.0178(4) -0.0055(3) 0.0057(4) 0.0013(4) C12 0.0316(5) 0.0246(4) 0.0170(3) -0.0023(3) 0.0087(3) -0.0015(3) C13 0.0205(4) 0.0157(3) 0.0145(3) -0.0002(2) 0.0026(3) 0.0003(3) C14 0.0162(3) 0.0153(3) 0.0156(3) -0.0015(2) 0.0050(3) -0.0009(3) C15 0.0212(4) 0.0246(4) 0.0227(4) -0.0013(3) 0.0094(3) 0.0038(3) C16 0.0222(4) 0.0258(4) 0.0307(4) -0.0003(4) 0.0069(3) 0.0066(3) C17 0.0234(4) 0.0234(4) 0.0263(4) 0.0029(3) 0.0005(3) 0.0020(3) C18 0.0281(5) 0.0240(4) 0.0177(3) 0.0015(3) 0.0038(3) 0.0004(3) C19 0.0230(4) 0.0186(4) 0.0158(3) -0.0009(3) 0.0064(3) 0.0010(3) C20 0.0241(4) 0.0176(3) 0.0210(4) -0.0013(3) 0.0088(3) -0.0042(3) F21 0.0380(3) 0.0216(3) 0.0261(3) -0.0092(2) 0.0125(2) -0.0086(2) F22 0.0235(3) 0.0280(3) 0.0342(3) -0.0046(2) 0.0136(2) -0.0086(2) F23 0.0368(3) 0.0197(3) 0.0323(3) 0.0072(2) 0.0101(3) -0.0043(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.4356(11) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C3 1.4038(10) . ? C3 C14 1.5262(12) . ? C3 C4 1.5478(11) . ? C3 C20 1.5569(12) . ? C4 O4 1.2054(10) . ? C4 N5 1.4038(11) . ? N5 C13 1.3895(11) . ? N5 N6 1.3921(10) . ? N6 N7 1.2803(11) . ? N7 C8 1.3933(12) . ? C8 C13 1.3924(12) . ? C8 C9 1.4004(13) . ? C9 C10 1.3821(16) . ? C9 H9A 0.9500 . ? C10 C11 1.4067(17) . ? C10 H10A 0.9500 . ? C11 C12 1.3872(14) . ? C11 H11A 0.9500 . ? C12 C13 1.3984(12) . ? C12 H12A 0.9500 . ? C14 C19 1.3932(11) . ? C14 C15 1.3968(12) . ? C15 C16 1.3907(14) . ? C15 H15A 0.9500 . ? C16 C17 1.3896(14) . ? C16 H16A 0.9500 . ? C17 C18 1.3888(15) . ? C17 H17A 0.9500 . ? C18 C19 1.3913(13) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 F22 1.3356(11) . ? C20 F21 1.3391(10) . ? C20 F23 1.3423(11) . ? 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 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 117.90(7) . . ? O2 C3 C14 107.86(6) . . ? O2 C3 C4 113.60(7) . . ? C14 C3 C4 109.75(7) . . ? O2 C3 C20 108.96(7) . . ? C14 C3 C20 108.69(7) . . ? C4 C3 C20 107.88(6) . . ? O4 C4 N5 119.22(8) . . ? O4 C4 C3 123.64(8) . . ? N5 C4 C3 117.09(7) . . ? C13 N5 N6 109.60(7) . . ? C13 N5 C4 127.14(7) . . ? N6 N5 C4 123.24(7) . . ? N7 N6 N5 108.42(7) . . ? N6 N7 C8 109.57(7) . . ? C13 C8 N7 108.77(7) . . ? C13 C8 C9 121.53(9) . . ? N7 C8 C9 129.68(9) . . ? C10 C9 C8 116.65(10) . . ? C10 C9 H9A 121.7 . . ? C8 C9 H9A 121.7 . . ? C9 C10 C11 121.35(9) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C12 C11 C10 122.58(10) . . ? C12 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? C11 C12 C13 115.55(9) . . ? C11 C12 H12A 122.2 . . ? C13 C12 H12A 122.2 . . ? N5 C13 C8 103.64(7) . . ? N5 C13 C12 134.01(8) . . ? C8 C13 C12 122.34(8) . . ? C19 C14 C15 119.59(8) . . ? C19 C14 C3 119.43(7) . . ? C15 C14 C3 120.97(7) . . ? C16 C15 C14 120.14(8) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C17 C16 C15 120.13(9) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C18 C17 C16 119.78(9) . . ? C18 C17 H17A 120.1 . . ? C16 C17 H17A 120.1 . . ? C17 C18 C19 120.40(9) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C18 C19 C14 119.95(8) . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? F22 C20 F21 107.30(8) . . ? F22 C20 F23 107.48(7) . . ? F21 C20 F23 106.75(7) . . ? F22 C20 C3 112.82(7) . . ? F21 C20 C3 109.13(7) . . ? F23 C20 C3 113.03(7) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 34.95 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.559 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.057