Ruthenium-catalyzed C-H functionalization of indoles and indolines with 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and indolines.
Chen, Jia-Zhen; Wang, Zhong-Xia; Organic & biomolecular chemistry 22 (2024) 5159–5169; doi:10.1039/d4ob00678j

data_7159960
_publ_section_title
;
 Ruthenium-catalyzed C-H functionalization of indoles and indolines with
 7-azabenzonorbornadienes: access to aminodihydronaphthyl indoles and
 indolines.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5159
_journal_page_last               5169
_journal_paper_doi               10.1039/d4ob00678j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H29 N3 O3'
_chemical_formula_sum            'C26 H29 N3 O3'
_chemical_formula_weight         431.52
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-26 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   24.63533(17)
_cell_length_b                   24.63533(17)
_cell_length_c                   20.65170(17)
_cell_measurement_reflns_used    24547
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6770
_cell_measurement_theta_min      4.6440
_cell_volume                     10854.33(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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   -116.00 -17.00   1.00    2.00    --  -41.51 -38.00-180.00   99
  2  \w    -82.00  39.00   1.00    2.00    --  -41.51  19.00  90.00  121
  3  \w      6.00  81.00   1.00    2.00    --   41.51 -99.00 120.00   75
  4  \w     58.00 129.00   1.00    2.00    --   41.51-178.00 150.00   71
  5  \w     61.00 130.00   1.00    2.00    --   41.51 178.00 -90.00   69
  6  \w     35.00 113.00   1.00    4.00    --  105.74-125.00   0.00   78
  7  \w     23.00 107.00   1.00    4.00    --  105.74 -94.00 -90.00   84
  8  \w    103.00 178.00   1.00    4.00    --  105.74  77.00  60.00   75
  9  \w    103.00 178.00   1.00    4.00    --  105.74  77.00  30.00   75
 10  \w     77.00 178.00   1.00    4.00    --  105.74  61.00 -90.00  101
 11  \w     97.00 177.00   1.00    4.00    --  105.74 125.00 -30.00   80
 12  \w     23.00 107.00   1.00    4.00    --  105.74 -94.00 120.00   84
 13  \w     53.00 178.00   1.00    4.00    --  105.74  15.00 150.00  125
 14  \w   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00 -90.00  101
 15  \w   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00   0.00  101
 16  \w   -114.00 -13.00   1.00    2.00    --  -41.51 -57.00  90.00  101
 17  \w     77.00 144.00   1.00    4.00    --  105.74  61.00-150.00   67
 18  \w     77.00 178.00   1.00    4.00    --  105.74  30.00   0.00  101
 19  \w    103.00 178.00   1.00    4.00    --  105.74  77.00-180.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147237000
_diffrn_orient_matrix_UB_12      -0.0421697000
_diffrn_orient_matrix_UB_13      -0.0600827000
_diffrn_orient_matrix_UB_21      0.0139380000
_diffrn_orient_matrix_UB_22      -0.0448950000
_diffrn_orient_matrix_UB_23      0.0391049000
_diffrn_orient_matrix_UB_31      -0.0693028000
_diffrn_orient_matrix_UB_32      -0.0376964000
_diffrn_orient_matrix_UB_33      0.0206300000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36158
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.777
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             4140
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00097(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0556P)^2^+5.8661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4487
_reflns_number_total             4802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00678j2.cif
_cod_data_source_block           cjz-20231124_auto
_cod_depositor_comments
'Adding full bibliography for 7159960--7159961.cif.'
_cod_original_cell_volume        10854.33(18)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7159960
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20N2O2
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.869
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
1.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C18(H18), C7(H7), C13(H13), C14(H14), C15(H15), C3(H3A), C16(H16),
 C17(H17), C6(H6), C2(H2), C1(H1)
1.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C20(H20A,H20B,H20C), C25(H25A,H25B,
 H25C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              28414
_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 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.820