Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for the Synthesis of 3-Amidoindoles and 3-Amidofurans.
Hu, Zhiyong; Tong, Xiaofeng; Liu, Guixia; Organic letters 18 (2016) 2058–2061; doi:10.1021/acs.orglett.6b00689

data_1543124
_publ_section_title
;
 Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for
 the Synthesis of 3-Amidoindoles and 3-Amidofurans.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2058
_journal_page_last               2061
_journal_paper_doi               10.1021/acs.orglett.6b00689
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C29 H21 Br N2 O3 S'
_chemical_formula_weight         557.45
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                106.400(2)
_cell_angle_beta                 94.409(2)
_cell_angle_gamma                93.758(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8056(9)
_cell_length_b                   10.1342(9)
_cell_length_c                   13.2604(13)
_cell_measurement_reflns_used    2329
_cell_measurement_temperature    130
_cell_measurement_theta_max      25.60
_cell_measurement_theta_min      2.51
_cell_volume                     1255.1(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12820
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.636
_diffrn_reflns_theta_min         1.609
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0577 before and 0.0420 after correction.
The Ratio of minimum to maximum transmission is 0.8884.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.014(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         10042
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0482P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.310
_reflns_Friedel_fraction_full    0.364
_reflns_Friedel_fraction_max     0.307
_reflns_number_gt                6561
_reflns_number_total             10042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00689_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1543124.cif.'
_cod_database_code               1543124
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              32042
_shelx_hkl_checksum              58704