Regiodivergent Oxidative Cross-Coupling of Catechols with Persistent tert-Carbon Radicals
Sugawara, Masumi; Ohnishi, Rikako; Ezawa, Tetsuya; Akakabe, Mai; Sawamura, Miki; Hojo, Daiki; Hashizume, Daisuke; Sohtome, Yoshihiro; Sodeoka, Mikiko; ACS Catalysis  (2020) 12770–12782; doi:10.1021/acscatal.0c03986

data_4518164
_publ_section_title
;
 Regiodivergent Oxidative Cross-Coupling of Catechols with Persistent
 tert-Carbon Radicals
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              12770
_journal_page_last               12782
_journal_paper_doi               10.1021/acscatal.0c03986
_journal_year                    2020
_chemical_formula_moiety         'C27 H27 N O5'
_chemical_formula_sum            'C27 H27 N O5'
_chemical_formula_weight         445.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.591(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9717(3)
_cell_length_b                   22.3087(6)
_cell_length_c                   15.0640(3)
_cell_measurement_reflns_used    36613
_cell_measurement_temperature    90
_cell_measurement_theta_max      32.7390
_cell_measurement_theta_min      2.0550
_cell_volume                     4695.06(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       CrystalClear
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    SV
_computing_publication_material  SHELXL-2014/7
_computing_structure_refinement  SHELXL-2014/7
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1501
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            183778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.631
_diffrn_source                   'Fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plate
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     621
_refine_ls_number_reflns         10750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0442P)^2^+2.7925P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7303
_reflns_number_total             10750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03986_si_004.cif
_cod_data_source_block           MSU156
_cod_original_cell_volume        4695.05(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518164
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.994
_shelx_estimated_absorpt_t_max   0.997
_oxdiff_exptl_absorpt_empirical_full_min 0.925
_oxdiff_exptl_absorpt_empirical_full_max 1.139
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              41306
_shelx_hkl_checksum              58816