Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols
Raji Reddy, Chada; Nair, Karna; Patil, Amol D.; Donthiri, Ramachandra Reddy; Grée, René; Organic & Biomolecular Chemistry 21 (2023) 1046–1055; doi:10.1039/D2OB02025D

data_7159069
_publ_section_title
;
 Domino alkyne insertion/aldol reaction/aromatization of 2-alkynyl
 indole-3-carbaldehyde with 1,3-diketones: entry to 2-indolyl phenols
;
_journal_issue                   5
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1046
_journal_page_last               1055
_journal_paper_doi               10.1039/D2OB02025D
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.773(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5837(11)
_cell_length_b                   14.4099(13)
_cell_length_c                   12.4674(13)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.9445
_cell_measurement_theta_min      2.16
_cell_volume                     1901.2(3)
_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  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_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  0.0692
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.429
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0560P)^2^+0.9995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3575
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02025d2.cif
_cod_data_source_block           KA918_0m
_cod_depositor_comments          'Adding full bibliography for 7159069.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159069
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              17708