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_7159961
_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 H31 N3 O3'
_chemical_formula_sum            'C26 H31 N3 O3'
_chemical_formula_weight         433.54
_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   mixed
_audit_creation_date             2024-01-17
_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                101.248(3)
_cell_angle_beta                 90.923(3)
_cell_angle_gamma                107.566(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1717(2)
_cell_length_b                   10.4991(4)
_cell_length_c                   17.0401(6)
_cell_measurement_reflns_used    4531
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8260
_cell_measurement_theta_min      4.7210
_cell_volume                     1195.87(8)
_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)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.969
_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   -108.00 -17.00   1.00    2.00    --  -41.51 -38.00 120.00   91
  2  \w    -66.00  33.00   1.00    2.00    --  -41.51  38.00 -60.00   99
  3  \w    100.00 128.00   1.00    2.00    --   41.51 178.00 150.00   28
  4  \w    -26.00  70.00   1.00    2.00    --   41.51 -57.00   0.00   96
  5  \w    100.00 126.00   1.00    2.00    --   41.51 178.00   0.00   26
  6  \w     35.00 132.00   1.00    8.00    --  105.74 -45.00 -90.00   97
  7  \w     63.00  88.00   1.00    8.00    --  105.74 -61.00 -60.00   25
  8  \w     52.00  95.00   1.00    8.00    --  105.74 -94.00  90.00   43
  9  \w    105.00 132.00   1.00    8.00    --  105.74  77.00-150.00   27
 10  \w     30.00  93.00   1.00    8.00    --  105.74 -94.00 150.00   63
 11  \w     45.00 129.00   1.00    8.00    --  105.74 -45.00 120.00   84
 12  \w     49.00 105.00   1.00    8.00    --  105.74 -94.00  30.00   56
 13  \w     30.00 102.00   1.00    8.00    --  105.74 -30.00   0.00   72
 14  \w     75.00 113.00   1.00    8.00    --  105.74-125.00 -90.00   38
 15  \w    114.00 167.00   1.00    8.00    --  105.74  77.00  60.00   53
 16  \w     34.00 106.00   1.00    8.00    --  105.74-100.00 -66.00   72
 17  \w     67.00 177.00   1.00    8.00    --  105.74  15.00-180.00  110
;
_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      0.0649955000
_diffrn_orient_matrix_UB_12      -0.0088805000
_diffrn_orient_matrix_UB_13      0.0848453000
_diffrn_orient_matrix_UB_21      -0.0982925000
_diffrn_orient_matrix_UB_22      -0.1559899000
_diffrn_orient_matrix_UB_23      -0.0206688000
_diffrn_orient_matrix_UB_31      0.1929013000
_diffrn_orient_matrix_UB_32      -0.0191352000
_diffrn_orient_matrix_UB_33      -0.0304304000
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7935
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         4.518
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87595
_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    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0039(5)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0610P)^2^+0.1406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3944
_reflns_number_total             4602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00678j2.cif
_cod_data_source_block           cjz-24-1-3_auto
_cod_depositor_comments
'Adding full bibliography for 7159960--7159961.cif.'
_cod_original_cell_volume        1195.87(7)
_cod_database_code               7159961
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20o2n2
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.873
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C1(H1A)
1.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
1.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C14(H14), C13(H13), C6(H6), C3(H3), C5(H5), C4(H4)
1.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              21866
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.669