A one-pot multicomponent tandem reaction for the rapid synthesis of 2-amino-3-benzylindoles.
Zhang, Pengyan; Liu, Chenrui; Dai, Maoyi; Wang, Guangyue; Huang, Yurong; Zhang, Lina; Liu, Cheng; He, Chengjie; Zhang, Xiaoxiang; Zhang, Zhuan; Liang, Taoyuan; Organic & biomolecular chemistry 23 (2025) 3393–3399; doi:10.1039/d5ob00187k

data_7160400
_publ_section_title
;
 A one-pot multicomponent tandem reaction for the rapid synthesis of
 2-amino-3-benzylindoles.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3393
_journal_page_last               3399
_journal_paper_doi               10.1039/d5ob00187k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C22 H26 F N3 O'
_chemical_formula_sum            'C22 H26 F N3 O'
_chemical_formula_weight         367.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2lvh43
_audit_creation_date             2024-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-09 deposited with the CCDC.	2025-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                108.227(4)
_cell_angle_beta                 91.024(3)
_cell_angle_gamma                113.106(4)
_cell_formula_units_Z            4
_cell_length_a                   11.1055(4)
_cell_length_b                   12.5847(6)
_cell_length_c                   16.5079(7)
_cell_measurement_reflns_used    5297
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.7880
_cell_measurement_theta_min      4.3910
_cell_volume                     1989.30(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     45.00  72.00   1.00    2.50    --   35.00 -99.00 -90.00   27
  2  \w    -34.00  49.00   1.00    2.50    --   35.00 -37.00  30.00   83
  3  \w     30.00  86.00   1.00    2.50    --   35.00-125.00  60.00   56
  4  \w     24.00 104.00   1.00    2.50    --   35.00  37.00   0.00   80
  5  \w     20.00 104.00   1.00    2.50    --   35.00  37.00-150.00   84
  6  \w     23.00  48.00   1.00    2.50    --   35.00  57.00-120.00   25
  7  \w     21.00  96.00   1.00    2.50    --   35.00  57.00 -90.00   75
  8  \w    -14.00  61.00   1.00    2.50    --   35.00 -77.00 120.00   75
  9  \w    105.00 131.00   1.00    2.50    --  105.75  61.00 120.00   26
 10  \w     45.00  96.00   1.00    2.50    --  105.75 -94.00  30.00   51
 11  \w    101.00 162.00   1.00    2.50    --  105.75  77.00  60.00   61
 12  \w     37.00 122.00   1.00    2.50    --  105.75 -45.00   0.00   85
 13  \w     85.00 176.00   1.00    2.50    --  105.75  30.00-150.00   91
 14  \w     56.00 123.00   1.00    2.50    --  105.75 -61.00  60.00   67
 15  \w    126.00 173.00   1.00    2.50    --  105.75  45.00 -60.00   47
 16  \w     72.00 108.00   1.00    2.50    --  105.75-111.00 120.00   36
 17  \w     75.00 108.00   1.00    2.50    --  105.75-111.00   0.00   33
 18  \w    122.00 168.00   1.00    2.50    --  105.75  77.00 150.00   46
 19  \w    133.00 168.00   1.00    2.50    --  105.75  77.00  30.00   35
 20  \w    135.00 173.00   1.00    2.50    --  105.75  61.00 120.00   38
 21  \w     39.00 107.00   1.00    2.50    --  105.75-111.00 -90.00   68
 22  \w    105.00 162.00   1.00    2.50    --  105.75  77.00  90.00   57
 23  \w    134.00 160.00   1.00    2.50    --  105.75  45.00  30.00   26
 24  \w     68.00 146.00   1.00    2.50    --  105.75 178.00 -60.00   78
 25  \w     47.00 119.00   1.00    2.50    --  105.75 -61.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205956000
_diffrn_orient_matrix_UB_12      0.1102674000
_diffrn_orient_matrix_UB_13      0.0819430000
_diffrn_orient_matrix_UB_21      -0.0842186000
_diffrn_orient_matrix_UB_22      -0.0892244000
_diffrn_orient_matrix_UB_23      0.0439986000
_diffrn_orient_matrix_UB_31      0.1258352000
_diffrn_orient_matrix_UB_32      -0.0055146000
_diffrn_orient_matrix_UB_33      0.0354944000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13185
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.807
_diffrn_reflns_theta_min         4.073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+0.1982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5875
_reflns_number_total             7446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00187k2.cif
_cod_data_source_block           exp_14899_auto
_cod_depositor_comments          'Adding full bibliography for 7160400.cif.'
_cod_original_cell_volume        1989.30(16)
_cod_database_code               7160400
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.878
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C32(H32A,H32B), C14(H14A,H14B), C36(H36A,H36B), C13(H13A,
 H13B), C33(H33A,H33B), C11(H11A,H11B), C12(H12A,H12B), C35(H35A,H35B),
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C38(H38), C39(H39), C19(H19), C20(H20), C41(H41), C5(H5), C17(H17), C42(H42),
 C16(H16), C30(H30), C8(H8), C27(H27), C7(H7), C29(H29)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C43(H43A,H43B,H43C), C23(H23A,H23B,H23C), C21(H21A,H21B,
 H21C), C44(H44A,H44B,H44C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              36761
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.857
_oxdiff_exptl_absorpt_empirical_full_min 0.586