data_threo12l _audit_creation_method SHELXL-97 _chemical_name_systematic ; (R*)-2-((S*)-5,5-bis(4-fluorophenyl)-3-methyl-2-oxooxazolidin-4-yl)-2- fluoro-N-methylacetamide ; _chemical_name_common ? _chemical_melting_point 494-495 _chemical_formula_moiety 'C19 H17 F3 N2 O3' _chemical_formula_sum 'C19 H17 F3 N2 O3' _chemical_formula_weight 378.35 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/a' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.394(3) _cell_length_b 24.341(7) _cell_length_c 9.028(3) _cell_angle_alpha 90.00 _cell_angle_beta 84.55(3) _cell_angle_gamma 90.00 _cell_volume 1836.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 16541 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9455 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17848 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4200 _reflns_number_gt 3192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'PROCESS-AUTO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'yadokari-XG' _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^)+(0.0594P)^2^+0.3496P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4200 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 O1 O 0.20086(13) 0.38283(5) 0.39680(11) 0.0472(3) Uani 1 1 d . . . C1 C 0.2033(2) 0.43080(8) 0.47398(19) 0.0555(4) Uani 1 1 d . . . O2 O 0.1376(2) 0.43582(7) 0.59785(15) 0.0876(5) Uani 1 1 d . . . N1 N 0.28850(18) 0.46863(6) 0.39146(16) 0.0520(4) Uani 1 1 d . . . C2 C 0.3079(3) 0.52477(8) 0.4436(3) 0.0807(7) Uani 1 1 d . . . H1 H 0.2133 0.5456 0.4298 0.121 Uiso 1 1 calc R . . H2 H 0.3984 0.5414 0.3879 0.121 Uiso 1 1 calc R . . H3 H 0.3247 0.5243 0.5473 0.121 Uiso 1 1 calc R . . C3 C 0.32771(18) 0.44914(6) 0.23999(16) 0.0400(3) Uani 1 1 d . . . H4 H 0.4358 0.4609 0.2028 0.048 Uiso 1 1 calc R . . C4 C 0.2063(2) 0.46925(6) 0.13627(18) 0.0465(4) Uani 1 1 d . . . H5 H 0.2257 0.4497 0.0413 0.056 Uiso 1 1 calc R . . F1 F 0.05191(12) 0.45661(4) 0.19849(13) 0.0651(3) Uani 1 1 d . . . C5 C 0.2228(2) 0.53041(7) 0.10649(18) 0.0482(4) Uani 1 1 d . . . O3 O 0.34898(17) 0.54677(5) 0.04246(17) 0.0742(4) Uani 1 1 d . . . N2 N 0.1000(2) 0.56213(6) 0.15176(17) 0.0557(4) Uani 1 1 d . . . C6 C 0.1070(3) 0.62162(8) 0.1363(3) 0.0859(7) Uani 1 1 d . . . H6 H 0.2107 0.6344 0.1573 0.129 Uiso 1 1 calc R . . H7 H 0.0264 0.6381 0.2048 0.129 Uiso 1 1 calc R . . H8 H 0.0886 0.6316 0.0364 0.129 Uiso 1 1 calc R . . C7 C 0.32530(17) 0.38632(6) 0.27271(15) 0.0365(3) Uani 1 1 d . . . C8 C 0.48124(18) 0.36593(6) 0.33030(15) 0.0367(3) Uani 1 1 d . . . C9 C 0.63083(19) 0.38198(6) 0.26762(18) 0.0462(4) Uani 1 1 d . . . H9 H 0.6389 0.4068 0.1889 0.055 Uiso 1 1 calc R . . C10 C 0.7689(2) 0.36158(7) 0.3204(2) 0.0531(4) Uani 1 1 d . . . H10 H 0.8693 0.3728 0.2789 0.064 Uiso 1 1 calc R . . C11 C 0.7541(2) 0.32468(7) 0.43501(19) 0.0513(4) Uani 1 1 d . . . F2 F 0.88871(14) 0.30475(5) 0.48876(14) 0.0765(4) Uani 1 1 d . . . C12 C 0.6088(2) 0.30635(8) 0.4968(2) 0.0603(5) Uani 1 1 d . . . H11 H 0.6021 0.2803 0.5725 0.072 Uiso 1 1 calc R . . C13 C 0.4725(2) 0.32739(7) 0.44442(18) 0.0527(4) Uani 1 1 d . . . H12 H 0.3728 0.3156 0.4862 0.063 Uiso 1 1 calc R . . C14 C 0.28148(18) 0.34908(6) 0.14888(16) 0.0380(3) Uani 1 1 d . . . C15 C 0.3595(2) 0.35484(7) 0.00670(17) 0.0495(4) Uani 1 1 d . . . H13 H 0.4336 0.3829 -0.0131 0.059 Uiso 1 1 calc R . . C16 C 0.3268(3) 0.31877(8) -0.1056(2) 0.0654(5) Uani 1 1 d . . . H14 H 0.3770 0.3227 -0.2014 0.078 Uiso 1 1 calc R . . C17 C 0.2191(3) 0.27734(8) -0.0721(2) 0.0708(6) Uani 1 1 d . . . F3 F 0.1897(2) 0.24202(6) -0.18322(17) 0.1166(6) Uani 1 1 d . . . C18 C 0.1426(3) 0.26980(8) 0.0657(3) 0.0684(6) Uani 1 1 d . . . H15 H 0.0710 0.2409 0.0845 0.082 Uiso 1 1 calc R . . C19 C 0.1734(2) 0.30610(6) 0.1775(2) 0.0507(4) Uani 1 1 d . . . H16 H 0.1216 0.3018 0.2725 0.061 Uiso 1 1 calc R . . H17 H 0.024(3) 0.5476(8) 0.206(2) 0.060(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0444(6) 0.0537(6) 0.0409(5) -0.0003(5) 0.0095(5) -0.0003(5) C1 0.0539(10) 0.0681(11) 0.0435(8) -0.0106(8) 0.0000(7) 0.0167(9) O2 0.0960(12) 0.1134(13) 0.0485(7) -0.0148(8) 0.0191(7) 0.0294(9) N1 0.0579(9) 0.0457(7) 0.0526(8) -0.0171(6) -0.0066(7) 0.0064(6) C2 0.1063(18) 0.0533(11) 0.0887(15) -0.0317(11) -0.0411(13) 0.0190(11) C3 0.0399(8) 0.0344(7) 0.0451(8) -0.0040(6) -0.0009(6) 0.0002(6) C4 0.0473(9) 0.0418(8) 0.0499(8) 0.0015(7) -0.0014(7) 0.0023(7) F1 0.0445(6) 0.0602(6) 0.0915(8) 0.0198(6) -0.0109(5) -0.0079(4) C5 0.0492(10) 0.0459(8) 0.0477(9) 0.0076(7) 0.0049(7) 0.0068(7) O3 0.0622(9) 0.0609(8) 0.0928(10) 0.0253(7) 0.0268(7) 0.0074(6) N2 0.0564(9) 0.0483(8) 0.0597(9) 0.0101(7) 0.0081(7) 0.0124(7) C6 0.1015(18) 0.0495(11) 0.1026(17) 0.0132(11) 0.0116(14) 0.0255(11) C7 0.0389(8) 0.0359(7) 0.0333(7) -0.0009(6) 0.0035(6) -0.0016(6) C8 0.0424(8) 0.0337(7) 0.0333(6) -0.0048(5) -0.0005(6) -0.0015(6) C9 0.0443(9) 0.0415(8) 0.0508(9) 0.0076(7) 0.0051(7) 0.0015(7) C10 0.0417(9) 0.0484(9) 0.0679(11) 0.0034(8) 0.0020(8) 0.0012(7) C11 0.0496(10) 0.0522(9) 0.0538(9) -0.0026(8) -0.0126(8) 0.0081(7) F2 0.0567(7) 0.0882(8) 0.0872(8) 0.0144(7) -0.0202(6) 0.0143(6) C12 0.0608(12) 0.0696(12) 0.0512(10) 0.0199(9) -0.0079(8) 0.0011(9) C13 0.0472(10) 0.0631(10) 0.0473(9) 0.0155(8) -0.0026(7) -0.0054(8) C14 0.0393(8) 0.0333(7) 0.0419(7) -0.0020(6) -0.0065(6) 0.0035(6) C15 0.0538(10) 0.0511(9) 0.0429(8) -0.0058(7) -0.0012(7) 0.0026(7) C16 0.0774(14) 0.0750(13) 0.0444(9) -0.0162(9) -0.0097(9) 0.0194(11) C17 0.0858(15) 0.0565(11) 0.0761(14) -0.0276(10) -0.0387(12) 0.0106(10) F3 0.1523(15) 0.1015(10) 0.1043(11) -0.0595(9) -0.0560(10) 0.0049(10) C18 0.0764(14) 0.0479(10) 0.0855(14) -0.0083(10) -0.0314(11) -0.0109(9) C19 0.0511(10) 0.0431(8) 0.0595(10) 0.0016(7) -0.0126(8) -0.0051(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 O1 C1 1.361(2) . ? O1 C7 1.4598(17) . ? C1 O2 1.205(2) . ? C1 N1 1.347(2) . ? N1 C3 1.455(2) . ? N1 C2 1.459(2) . ? C2 H1 0.9600 . ? C2 H2 0.9600 . ? C2 H3 0.9600 . ? C3 C4 1.528(2) . ? C3 C7 1.5571(19) . ? C3 H4 0.9800 . ? C4 F1 1.397(2) . ? C4 C5 1.517(2) . ? C4 H5 0.9800 . ? C5 O3 1.224(2) . ? C5 N2 1.322(2) . ? N2 C6 1.455(2) . ? N2 H17 0.84(2) . ? C6 H6 0.9600 . ? C6 H7 0.9600 . ? C6 H8 0.9600 . ? C7 C14 1.511(2) . ? C7 C8 1.536(2) . ? C8 C9 1.384(2) . ? C8 C13 1.390(2) . ? C9 C10 1.386(2) . ? C9 H9 0.9300 . ? C10 C11 1.367(2) . ? C10 H10 0.9300 . ? C11 F2 1.361(2) . ? C11 C12 1.367(3) . ? C12 C13 1.378(3) . ? C12 H11 0.9300 . ? C13 H12 0.9300 . ? C14 C15 1.391(2) . ? C14 C19 1.393(2) . ? C15 C16 1.388(2) . ? C15 H13 0.9300 . ? C16 C17 1.369(3) . ? C16 H14 0.9300 . ? C17 C18 1.357(3) . ? C17 F3 1.361(2) . ? C18 C19 1.385(3) . ? C18 H15 0.9300 . ? C19 H16 0.9300 . ? 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 O1 C7 107.37(12) . . ? O2 C1 N1 128.04(18) . . ? O2 C1 O1 122.29(19) . . ? N1 C1 O1 109.67(13) . . ? C1 N1 C3 110.96(13) . . ? C1 N1 C2 122.12(16) . . ? C3 N1 C2 125.88(16) . . ? N1 C2 H1 109.5 . . ? N1 C2 H2 109.5 . . ? H1 C2 H2 109.5 . . ? N1 C2 H3 109.5 . . ? H1 C2 H3 109.5 . . ? H2 C2 H3 109.5 . . ? N1 C3 C4 111.52(13) . . ? N1 C3 C7 98.30(11) . . ? C4 C3 C7 115.68(12) . . ? N1 C3 H4 110.3 . . ? C4 C3 H4 110.3 . . ? C7 C3 H4 110.3 . . ? F1 C4 C5 110.66(13) . . ? F1 C4 C3 109.28(13) . . ? C5 C4 C3 111.59(13) . . ? F1 C4 H5 108.4 . . ? C5 C4 H5 108.4 . . ? C3 C4 H5 108.4 . . ? O3 C5 N2 124.79(16) . . ? O3 C5 C4 117.61(14) . . ? N2 C5 C4 117.60(15) . . ? C5 N2 C6 121.89(17) . . ? C5 N2 H17 117.3(13) . . ? C6 N2 H17 119.7(13) . . ? N2 C6 H6 109.5 . . ? N2 C6 H7 109.5 . . ? H6 C6 H7 109.5 . . ? N2 C6 H8 109.5 . . ? H6 C6 H8 109.5 . . ? H7 C6 H8 109.5 . . ? O1 C7 C14 109.03(12) . . ? O1 C7 C8 106.99(11) . . ? C14 C7 C8 109.37(11) . . ? O1 C7 C3 101.43(11) . . ? C14 C7 C3 116.63(12) . . ? C8 C7 C3 112.67(12) . . ? C9 C8 C13 118.40(14) . . ? C9 C8 C7 122.67(13) . . ? C13 C8 C7 118.83(13) . . ? C8 C9 C10 120.93(15) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 118.48(16) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? F2 C11 C10 119.04(16) . . ? F2 C11 C12 118.48(16) . . ? C10 C11 C12 122.48(16) . . ? C11 C12 C13 118.44(16) . . ? C11 C12 H11 120.8 . . ? C13 C12 H11 120.8 . . ? C12 C13 C8 121.22(16) . . ? C12 C13 H12 119.4 . . ? C8 C13 H12 119.4 . . ? C15 C14 C19 119.21(14) . . ? C15 C14 C7 119.72(13) . . ? C19 C14 C7 120.86(13) . . ? C16 C15 C14 120.14(17) . . ? C16 C15 H13 119.9 . . ? C14 C15 H13 119.9 . . ? C17 C16 C15 118.45(18) . . ? C17 C16 H14 120.8 . . ? C15 C16 H14 120.8 . . ? C18 C17 F3 119.1(2) . . ? C18 C17 C16 123.19(17) . . ? F3 C17 C16 117.7(2) . . ? C17 C18 C19 118.49(18) . . ? C17 C18 H15 120.8 . . ? C19 C18 H15 120.8 . . ? C18 C19 C14 120.50(18) . . ? C18 C19 H16 119.7 . . ? C14 C19 H16 119.7 . . ? 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 C7 O1 C1 O2 -164.58(18) . . . . ? C7 O1 C1 N1 14.90(18) . . . . ? O2 C1 N1 C3 -171.41(19) . . . . ? O1 C1 N1 C3 9.16(19) . . . . ? O2 C1 N1 C2 -2.5(3) . . . . ? O1 C1 N1 C2 178.08(16) . . . . ? C1 N1 C3 C4 95.08(16) . . . . ? C2 N1 C3 C4 -73.3(2) . . . . ? C1 N1 C3 C7 -26.81(16) . . . . ? C2 N1 C3 C7 164.78(17) . . . . ? N1 C3 C4 F1 -51.59(17) . . . . ? C7 C3 C4 F1 59.61(16) . . . . ? N1 C3 C4 C5 71.13(17) . . . . ? C7 C3 C4 C5 -177.67(12) . . . . ? F1 C4 C5 O3 -175.08(16) . . . . ? C3 C4 C5 O3 63.0(2) . . . . ? F1 C4 C5 N2 5.0(2) . . . . ? C3 C4 C5 N2 -116.93(17) . . . . ? O3 C5 N2 C6 -3.5(3) . . . . ? C4 C5 N2 C6 176.41(18) . . . . ? C1 O1 C7 C14 -154.21(12) . . . . ? C1 O1 C7 C8 87.62(14) . . . . ? C1 O1 C7 C3 -30.61(15) . . . . ? N1 C3 C7 O1 33.14(13) . . . . ? C4 C3 C7 O1 -85.64(14) . . . . ? N1 C3 C7 C14 151.40(12) . . . . ? C4 C3 C7 C14 32.62(18) . . . . ? N1 C3 C7 C8 -80.91(14) . . . . ? C4 C3 C7 C8 160.31(12) . . . . ? O1 C7 C8 C9 -154.72(13) . . . . ? C14 C7 C8 C9 87.33(16) . . . . ? C3 C7 C8 C9 -44.10(18) . . . . ? O1 C7 C8 C13 29.04(17) . . . . ? C14 C7 C8 C13 -88.91(16) . . . . ? C3 C7 C8 C13 139.66(14) . . . . ? C13 C8 C9 C10 -2.1(2) . . . . ? C7 C8 C9 C10 -178.37(14) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 F2 -179.39(15) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? F2 C11 C12 C13 178.69(16) . . . . ? C10 C11 C12 C13 -2.2(3) . . . . ? C11 C12 C13 C8 0.7(3) . . . . ? C9 C8 C13 C12 1.4(3) . . . . ? C7 C8 C13 C12 177.81(16) . . . . ? O1 C7 C14 C15 164.66(13) . . . . ? C8 C7 C14 C15 -78.67(16) . . . . ? C3 C7 C14 C15 50.62(19) . . . . ? O1 C7 C14 C19 -20.62(19) . . . . ? C8 C7 C14 C19 96.04(16) . . . . ? C3 C7 C14 C19 -134.67(15) . . . . ? C19 C14 C15 C16 1.4(2) . . . . ? C7 C14 C15 C16 176.20(15) . . . . ? C14 C15 C16 C17 -1.1(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C15 C16 C17 F3 -179.37(17) . . . . ? F3 C17 C18 C19 -179.87(18) . . . . ? C16 C17 C18 C19 0.7(3) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 -0.6(2) . . . . ? C7 C14 C19 C18 -175.37(15) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.204 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.037