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_4038440
_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         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.772(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.662(2)
_cell_length_b                   10.9561(8)
_cell_length_c                   10.6849(8)
_cell_measurement_reflns_used    1581
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.6860
_cell_measurement_theta_min      3.8400
_cell_volume                     3448.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -99.00  -59.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -90.0000 40

  2 omega  -44.00  -13.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   90.0000 31

  3 omega   36.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   30.0000 43

  4 omega  -26.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  120.0000 113
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0074749000
_diffrn_orient_matrix_UB_12      0.0436729000
_diffrn_orient_matrix_UB_13      0.0419990000
_diffrn_orient_matrix_UB_21      -0.0202474000
_diffrn_orient_matrix_UB_22      0.0084254000
_diffrn_orient_matrix_UB_23      -0.0415663000
_diffrn_orient_matrix_UB_31      -0.0106769000
_diffrn_orient_matrix_UB_32      -0.0469691000
_diffrn_orient_matrix_UB_33      0.0314090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6284
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.52
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                2568
_reflns_number_total             3404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00475_si_006.cif
_cod_data_source_block           zhangzh_1214
_cod_database_code               4038440
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_date_sample_data_collection 2018-12-14
_olex2_submission_special_instructions 'No special instructions were received'