Site-Selective and Chemoselective C–H Functionalization for the Synthesis of Spiroaminals via a Silver-Catalyzed Nitrene Transfer Reaction
Harada, Shingo; Kobayashi, Mayu; Kono, Masato; Nemoto, Tetsuhiro; ACS Catalysis 10 (2020) 13296–13304; doi:10.1021/acscatal.0c04057

data_4518195
_publ_section_title
;
 Site-Selective and Chemoselective C--H Functionalization for the
 Synthesis of Spiroaminals via a Silver-Catalyzed Nitrene Transfer
 Reaction
;
_journal_issue                   22
_journal_name_full               'ACS Catalysis'
_journal_page_first              13296
_journal_page_last               13304
_journal_paper_doi               10.1021/acscatal.0c04057
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C20 H19 Br N2 O3'
_chemical_formula_sum            'C20 H19 Br N2 O3'
_chemical_formula_weight         415.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   11.3768(2)
_cell_length_b                   13.3425(2)
_cell_length_c                   24.5874(5)
_cell_measurement_reflns_used    30487
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.31
_cell_volume                     3732.24(11)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41269
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.200
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         3.595
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.190
_exptl_absorpt_correction_T_max  0.727
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.39
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2990 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.006(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0238P)^2^+1.6837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0817
_reflns_number_gt                5377
_reflns_number_total             6810
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs0c04057_si_002.cif
_cod_data_source_block           20200522kobayashi1
_cod_depositor_comments          'Adding full bibliography for 4518195.cif.'
_cod_original_cell_volume        3732.26(12)
_cod_database_code               4518195