In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors.
Tasker, Nikhil R.; Rastelli, Ettore J.; Blanco, Isabella K.; Burnett, James C.; Sharlow, Elizabeth R.; Lazo, John S.; Wipf, Peter; Organic & biomolecular chemistry 17 (2019) 2448–2466; doi:10.1039/c9ob00025a

data_7156672
_publ_section_title
;
 In-flow photooxygenation of aminothienopyridinones generates
 iminopyridinedione PTP4A3 phosphatase inhibitors.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2448
_journal_page_last               2466
_journal_paper_doi               10.1039/c9ob00025a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C13 H7 N O3 S'
_chemical_formula_weight         257.26
_chemical_name_common            2-phenylthieno[3,2-c]pyridine-4,6,7(5H)-trione
_chemical_name_systematic        'Compound 3'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-11-21 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                69.319(6)
_cell_angle_beta                 82.283(6)
_cell_angle_gamma                83.399(5)
_cell_formula_units_Z            2
_cell_length_a                   5.4276(4)
_cell_length_b                   9.6873(7)
_cell_length_c                   10.8442(8)
_cell_measurement_reflns_used    1048
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      67.72
_cell_measurement_theta_min      4.38
_cell_volume                     527.20(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6359
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.418
_diffrn_reflns_theta_min         4.380
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       plate
_exptl_crystal_F_000             264
_exptl_crystal_size_max          .03
_exptl_crystal_size_mid          .02
_exptl_crystal_size_min          .005
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0680P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1464
_reflns_number_total             1890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00025a3.cif
_cod_data_source_block           compound_3
_cod_depositor_comments          'Adding full bibliography for 7156672.cif.'
_cod_database_code               7156672
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              55579