One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs<sub>2</sub>CO<sub>3</sub>-mediated addition/aromatization reaction.
Huang, Chaoman; Jin, Zefeng; Zhang, Bei; Zhou, Yuanyuan; Lin, Huiting; Kang, Honglan; Shen, Guodong; Lv, Xin; Organic & biomolecular chemistry 21 (2023) 4245–4256; doi:10.1039/d3ob00316g

data_7159327
_publ_section_title
;
 One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a
 sequential dearomatization and Ag-catalyzed
 cyclization/Cs<sub>2</sub>CO<sub>3</sub>-mediated addition/aromatization
 reaction.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4245
_journal_page_last               4256
_journal_paper_doi               10.1039/d3ob00316g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C25 H21 N3 O2 S'
_chemical_formula_sum            'C25 H21 N3 O2 S'
_chemical_formula_weight         427.51
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-27 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.245(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6654(6)
_cell_length_b                   23.1002(14)
_cell_length_c                   12.1164(9)
_cell_measurement_reflns_used    7202
_cell_measurement_temperature    152.00
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.83
_cell_volume                     2123.3(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      152.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.826
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0558P)^2^+0.9373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3486
_reflns_number_total             4846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00316g2.cif
_cod_data_source_block           2022062002_0m
_cod_depositor_comments          'Adding full bibliography for 7159327.cif.'
_cod_database_code               7159327
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              9087
_olex2_submission_special_instructions 'No special instructions were received'