Electrochemical triamination of alkynes: controllable synthesis of functionalized indolines and indoles
Meng, Xiangtai; Xu, Hehua; Liu, Rui; Zheng, Yu; Huang, Shenlin; Green Chemistry 24 (2022) 4754–4760; doi:10.1039/D2GC01129H

data_7244984
_publ_section_title
;
 Electrochemical triamination of alkynes: controllable synthesis of
 functionalized indolines and indoles
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              4754
_journal_page_last               4760
_journal_paper_doi               10.1039/D2GC01129H
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C27 H21 N3 O2 S'
_chemical_formula_sum            'C27 H21 N3 O2 S'
_chemical_formula_weight         451.53
_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_creation_date             2020-08-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-06-16 deposited with the CCDC.	2022-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                89.459(7)
_cell_angle_beta                 81.983(8)
_cell_angle_gamma                73.840(8)
_cell_formula_units_Z            4
_cell_length_a                   9.8859(10)
_cell_length_b                   9.9067(9)
_cell_length_c                   23.766(2)
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3040
_cell_measurement_theta_min      2.4700
_cell_volume                     2212.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -16.00  85.00   1.00    4.50    --   11.90  57.00   0.00  101
  2  \w    -16.00  79.00   1.00    4.50    --   11.90  77.00 120.00   95
  3  \w     28.00  53.00   1.00    4.50    --   11.90 -99.00-150.00   25
  4  \w    -56.00  37.00   1.00    4.50    --   11.90 -57.00-150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0159782000
_diffrn_orient_matrix_UB_12      0.0619009000
_diffrn_orient_matrix_UB_13      0.0173206000
_diffrn_orient_matrix_UB_21      -0.0278193000
_diffrn_orient_matrix_UB_22      0.0408116000
_diffrn_orient_matrix_UB_23      -0.0226131000
_diffrn_orient_matrix_UB_31      -0.0683124000
_diffrn_orient_matrix_UB_32      -0.0080472000
_diffrn_orient_matrix_UB_33      0.0099036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15379
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.141
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         7780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0401P)^2^+9.8749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6068
_reflns_number_total             7780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc01129h2.cif
_cod_data_source_block           mxt-1-2
_cod_depositor_comments
'Adding full bibliography for 7244984--7244985.cif.'
_cod_database_code               7244984
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C43(H43), C44(H44), C45(H45), C46(H46),
  C47(H47), C49(H49), C50(H50), C52(H52), C53(H53)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              15878
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.581