Photocatalyst-Free Singlet Oxygen-Induced Oxygenation: A Strategy for the Preparation of 5-Cyano-2-Pyridones Driven by Blue-Light Irradiation.
Zhang, Mengmeng; Lan, Hanyang; Li, Nan; Zhong, Qidi; Zhu, Hao; Liu, Chunyan; Zhao, Hong-Wu; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00963

data_4038454
_publ_section_title
;
 Photocatalyst-Free Singlet Oxygen-Induced Oxygenation: A Strategy for the
 Preparation of 5-Cyano-2-Pyridones Driven by Blue-Light Irradiation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00963
_journal_year                    2020
_chemical_formula_moiety         'C19 H13 Cl N2 O'
_chemical_formula_sum            'C19 H13 Cl N2 O'
_chemical_formula_weight         320.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.474(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.575(9)
_cell_length_b                   4.3839(12)
_cell_length_c                   25.202(7)
_cell_measurement_reflns_used    2013
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.51
_cell_measurement_theta_min      3.24
_cell_volume                     3268.1(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  'SHELXTL (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Bruker, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7395
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.377
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1460P)^2^+0.3432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2004
_reflns_number_total             2864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00963_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3268.2(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038454
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.940
_shelx_res_checksum              80525
_shelx_hkl_checksum              81829