Ortho-Selective C-H Arylation of Phenols with N-Carboxyindoles under Brønsted Acid- or Cu(I)-Catalysis
Nguyen, Nguyen Hoang; Oh, Soo Min; Park, Cheol-Min; Shin, Seunghoon; Chemical Science  (2022) –; doi:10.1039/D1SC06157G

data_1565839
_publ_section_title
;
 Ortho-Selective C-H Arylation of Phenols with N-Carboxyindoles under
 Br\/onsted Acid- or Cu(I)-Catalysis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06157G
_journal_year                    2022
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1887(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8503(3)
_cell_length_b                   8.8759(2)
_cell_length_c                   19.9348(5)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.98
_cell_volume                     1889.57(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33546
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.003
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7249
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SHELXL-2014/7 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0139(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0564P)^2^+0.7216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3884
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06157g3.cif
_cod_data_source_block           OSM-V-7
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1565839
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              21736
_shelx_hkl_checksum              8487