Oxidative Cyclization of <i>o</i>-(1-Hydroxy-2-alkynyl)-<i>N</i>-tosylanilides for Synthesis of 4-Quinolones.
Ueda, Jun-Ichi; Enomoto, Yuuki; Seki, Mizuki; Konishi, Takuma; Ogasawara, Masamichi; Yoshida, Kazuhiro; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00245

data_4038325
_publ_section_title
;
 Oxidative Cyclization of
 <i>o</i>-(1-Hydroxy-2-alkynyl)-<i>N</i>-tosylanilides for Synthesis of
 4-Quinolones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00245
_journal_year                    2020
_chemical_formula_sum            'C22 H17 N O3 S'
_chemical_formula_weight         375.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.8943(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4905(10)
_cell_length_b                   12.0256(7)
_cell_length_c                   9.3656(6)
_cell_measurement_reflns_used    4642
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.2186
_cell_measurement_theta_min      2.5003
_cell_volume                     1834.94(19)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10488
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.767
_diffrn_reflns_theta_min         1.25
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.537
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.5523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3685
_reflns_number_total             4323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00245_si_003.cif
_cod_data_source_block           I
_cod_database_code               4038325
_shelx_res_checksum              12659
_shelx_hkl_checksum              96063