Stereoselective Synthesis of Fluorinated 2,3-Dihydroquinolin-4(1H)-ones via a One-Pot Multistep Transformation
Feng Li; Jing Nie; Jun-Wei Wu; Yan Zheng; Jun-An Ma; Journal of Organic Chemistry 77 (2012) 2398–2406; doi:10.1021/jo202693x

data_4027046
_publ_section_title
;
 Stereoselective Synthesis of Fluorinated 2,3-Dihydroquinolin-4(1H)-ones
 via a One-Pot Multistep Transformation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2398
_journal_page_last               2406
_journal_paper_doi               10.1021/jo202693x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C27 H28 F N O5 S'
_chemical_formula_weight         497.56
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                83.058(12)
_cell_angle_beta                 84.028(13)
_cell_angle_gamma                77.561(12)
_cell_formula_units_Z            2
_cell_length_a                   8.9990(6)
_cell_length_b                   10.3477(4)
_cell_length_c                   13.9922(11)
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     1258.93(15)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'RIGAKU MERCURY375R'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13226
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.2816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                4832
_reflns_number_total             5748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202693x_si_002.cif
_cod_data_source_block           110929a
_cod_original_cell_volume        1258.93(14)
_cod_database_code               4027046