Visible Light-Induced and Singlet Oxygen-Mediated Photochemical Conversion of 4-Hydroxy-alpha-benzopyrones to 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using Rose Bengal as a Photosensitizer.
Brahmachari, Goutam; Karmakar, Indrajit; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00726

data_4038529
_publ_section_title
;
 Visible Light-Induced and Singlet Oxygen-Mediated Photochemical
 Conversion of 4-Hydroxy-alpha-benzopyrones to
 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using
 Rose Bengal as a Photosensitizer.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00726
_journal_year                    2020
_chemical_formula_moiety         'C13 H11 N O4, H2 O'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24
_chemical_name_systematic
;
 2-Hydroxy-5-methyl-3-oxo-N-(prop-2-yn-1-yl)-2,3-dihydrobenzofuran-2-carboxamide
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.923(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7637(7)
_cell_length_b                   14.5153(8)
_cell_length_c                   7.3338(4)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.3910
_cell_measurement_theta_min      2.2500
_cell_volume                     1225.26(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelxl97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9974
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3533
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.0308P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1330
_reflns_number_gt                1762
_reflns_number_total             2382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00726_si_002.cif
_cod_data_source_block           gb_1470_lt_mo
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4038529