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_4027045
_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 H26 F N O5 S'
_chemical_formula_weight         495.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.418(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.729(4)
_cell_length_b                   17.138(7)
_cell_length_c                   15.269(6)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2543.6(18)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26184
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.4974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                4480
_reflns_number_total             5780
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202693x_si_001.cif
_cod_data_source_block           110919a
_cod_original_cell_volume        2543.5(18)
_cod_database_code               4027045