Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans.
Zhang, Zhe; Zhang, Bo-Sheng; Li, Kai-Li; An, Yang; Liu, Ce; Gou, Xue-Ya; Liang, Yong-Min; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00475

data_4038442
_publ_section_title
;
 Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and
 Benzofurans.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00475
_journal_year                    2020
_chemical_formula_moiety         'C22 H21 Cl N2 O'
_chemical_formula_sum            'C22 H21 Cl N2 O'
_chemical_formula_weight         364.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.224(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2878(3)
_cell_length_b                   16.3406(4)
_cell_length_c                   9.9479(3)
_cell_measurement_reflns_used    2762
_cell_measurement_temperature    292.8(2)
_cell_measurement_theta_max      70.0160
_cell_measurement_theta_min      10.0950
_cell_volume                     1834.87(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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      8.00  41.00   1.00    1.00    --    0.00  57.00 -60.00   33
  2  \w     37.00 119.00   1.00    1.00    --   54.00  38.00-120.00   82
  3  \w    151.00 178.00   1.00    1.00    --  108.00  38.00 -60.00   27
  4  \w     84.00 136.00   1.00    1.00    --  108.00  38.00 -60.00   52
  5  \w     72.00 138.00   1.00    1.00    --  108.00 -77.00-180.00   66
  6  \w     43.00 113.00   1.00    1.00    --  108.00-111.00  30.00   70
  7  \w     36.00  96.00   1.00    1.00    --   54.00 -99.00  90.00   60
  8  \w     38.00 134.00   1.00    1.00    --  108.00 -38.00 120.00   96
  9  \w     24.00  67.00   1.00    1.00    --   54.00-125.00  60.00   43
 10  \w      1.00  32.00   1.00    1.00    --   54.00 -99.00  90.00   31
 11  \w    -13.00  37.00   1.00    1.00    --    0.00  57.00 150.00   50
 12  \w     60.00  87.00   1.00    1.00    --  108.00 178.00-180.00   27
 13  \w     29.00  56.00   1.00    1.00    --    0.00  57.00-180.00   27
 14  \w     51.00  77.00   1.00    1.00    --   54.00 -99.00  30.00   26
 15  \w     71.00 111.00   1.00    1.00    --   54.00  19.00-180.00   40
 16  \w      3.00  28.00   1.00    1.00    --   54.00 -99.00  30.00   25
 17  \w     42.00 108.00   1.00    1.00    --  108.00-111.00-150.00   66
 18  \w    125.00 151.00   1.00    1.00    --  108.00 111.00  90.00   26
 19  \w     81.00 107.00   1.00    1.00    --  108.00 -63.00   0.00   26
 20  \w    152.00 177.00   1.00    1.00    --  108.00 111.00-120.00   25
 21  \w    111.00 168.00   1.00    1.00    --  108.00  63.00 120.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1004252000
_diffrn_orient_matrix_UB_12      0.0193267000
_diffrn_orient_matrix_UB_13      0.1002796000
_diffrn_orient_matrix_UB_21      -0.0216258000
_diffrn_orient_matrix_UB_22      0.0922588000
_diffrn_orient_matrix_UB_23      -0.0206394000
_diffrn_orient_matrix_UB_31      -0.0897250000
_diffrn_orient_matrix_UB_32      -0.0004596000
_diffrn_orient_matrix_UB_33      0.1163605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0238
_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       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7010
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34933
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0540P)^2^+0.7252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2737
_reflns_number_total             3244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00475_si_005.cif
_cod_data_source_block           zhangzh_0701-1
_cod_original_cell_volume        1834.86(8)
_cod_database_code               4038442
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.94
_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:
 C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C17(H17), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              37618
_shelx_hkl_checksum              71142
_olex2_date_sample_data_collection 2019-07-01
_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 2.513
_oxdiff_exptl_absorpt_empirical_full_min 0.565