Gold-Catalyzed Synthesis of 6-Hydroxyindoles from Alkynylcyclohexadienones and Substituted Amines.
Kadiyala, Veerabhushanam; Bharath Kumar, Perla; Balasubramanian, Sridhar; Karunakar, Galla V.; The Journal of organic chemistry 84 (2019) 12228–12236; doi:10.1021/acs.joc.9b02023

data_4034495
_publ_section_title
;
 Gold-Catalyzed Synthesis of 6-Hydroxyindoles from
 Alkynylcyclohexadienones and Substituted Amines.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12228
_journal_page_last               12236
_journal_paper_doi               10.1021/acs.joc.9b02023
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H16 Cl N O2, C2 H6 O'
_chemical_formula_sum            'C23 H22 Cl N O3'
_chemical_formula_weight         395.86
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.0058(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0192(2)
_cell_length_b                   10.5869(2)
_cell_length_c                   17.8709(4)
_cell_measurement_reflns_used    8455
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.86
_cell_measurement_theta_min      2.69
_cell_volume                     2053.09(7)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015b)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            31118
_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         26.249
_diffrn_reflns_theta_min         2.245
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0560
_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^)+(0.0636P)^2^+1.1828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2897
_reflns_number_total             4138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02023_si_003.cif
_cod_data_source_block           KA730_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034495
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              59366
_shelx_hkl_checksum              1858