Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides.
Yuan, Yu-Chao; Bruneau, Christian; Dorcet, Vincent; Roisnel, Thierry; Gramage-Doria, Rafael; The Journal of organic chemistry 84 (2019) 1898–1907; doi:10.1021/acs.joc.8b02899

data_4033760
_publ_section_title
;
 Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1898
_journal_page_last               1907
_journal_paper_doi               10.1021/acs.joc.8b02899
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H11 N O3'
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 103.979(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8718(14)
_cell_length_b                   8.0647(12)
_cell_length_c                   13.948(2)
_cell_measurement_reflns_used    5856
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5267
_cell_measurement_theta_min      3.0093
_cell_measurement_wavelength     0.71073
_cell_volume                     1186.7(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1120
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_min         2.142
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.7329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1919
_reflns_number_total             2739
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02899_si_001.cif
_cod_data_source_block           RGYYC3X110
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4033760
_shelx_res_checksum              22104
_shelx_hkl_checksum              61715