Me<sub>3</sub>SiBr-promoted cascade electrophilic thiocyanation/cyclization of <i>ortho</i>-alkynylanilines to synthesize indole derivatives.
Wang, Qing; Shao, Chukai; Hua, Ruirui; Yin, Hongquan; Chen, Fu-Xue; Organic & biomolecular chemistry 22 (2024) 4031–4035; doi:10.1039/d4ob00367e

data_7159917
_publ_section_title
;
 Me<sub>3</sub>SiBr-promoted cascade electrophilic
 thiocyanation/cyclization of <i>ortho</i>-alkynylanilines to synthesize
 indole derivatives.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4031
_journal_page_last               4035
_journal_paper_doi               10.1039/d4ob00367e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C19 H15 Ca N2 O S'
_chemical_formula_weight         359.47
_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   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-12-22 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.255(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.39200(10)
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_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_cell_volume                     1732.20(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16805
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.201
_diffrn_reflns_theta_min         4.628
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    4.304
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       clear_block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1639P)^2^+1.1485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2472
_refine_ls_wR_factor_ref         0.2539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3143
_reflns_number_total             3506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00367e2.cif
_cod_data_source_block           test
_cod_depositor_comments          'Adding full bibliography for 7159917.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159917
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              30896