Copper-Catalyzed Tandem O-Vinylation of Arylhydroxylamines/[3,3]-Rearrangement/Cyclization: Synthesis of Highly Substituted Indoles and Benzoindoles
Yuan, Hairui; Guo, Lirong; Liu, Fengting; Miao, Zechen; Feng, Lei; Gao, Hongyin; ACS Catalysis 9 (2019) 3906–; doi:10.1021/acscatal.9b00470

data_4514691
_publ_section_title
;
 Copper-Catalyzed Tandem O-Vinylation of
 Arylhydroxylamines/[3,3]-Rearrangement/Cyclization: Synthesis of Highly
 Substituted Indoles and Benzoindoles
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3906
_journal_paper_doi               10.1021/acscatal.9b00470
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C25 H17 N O'
_chemical_formula_sum            'C25 H17 N O'
_chemical_formula_weight         347.39
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.293(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.618(2)
_cell_length_b                   11.775(3)
_cell_length_c                   18.166(5)
_cell_measurement_reflns_used    1259
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.428
_cell_measurement_theta_min      2.437
_cell_volume                     1794.0(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.078
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0485 before and 0.0440 after correction. The Ratio of minimum to maximum transmission is 0.9446. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0590P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1845
_reflns_number_total             3162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00470_si_002.cif
_cod_data_source_block           180324a_0m
_cod_original_cell_volume        1794.2(8)
_cod_database_code               4514691
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C18(H18), C12(H12), C4(H4), C13(H13), C17(H17), C15(H15), C6(H6),
 C25(H25), C16(H16), C21(H21), C3(H3), C23(H23), C24(H24), C2(H2), C1(H1),
 C22(H22)
;
_shelx_res_checksum              39792
_shelx_hkl_checksum              45601
_olex2_submission_special_instructions 'No special instructions were received'