Palladium-catalyzed Regioselective Intramolecular Direct Arylation of N-(o-Bromophenyl)-3-Indolecarboxamides: Access to Spiro-Indoline-3,3´-Oxindoles and 5,11-Dihydro-6H-indolo[3,2-c]quinolin-6-ones
Xu, Xiaobing; Liu, Jianchao; Lu, Lin; Wang, Furong; Yin, BiaoLin; Chem. Commun.  (2017) –; doi:10.1039/C7CC02256E

data_7120273
_publ_section_title
;
 Palladium-catalyzed Regioselective Intramolecular Direct Arylation of
 N-(o-Bromophenyl)-3-Indolecarboxamides: Access to
 Spiro-Indoline-3,3&#x00B4;-Oxindoles and
 5,11-Dihydro-6H-indolo[3,2-c]quinolin-6-ones
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02256E
_journal_year                    2017
_chemical_formula_moiety         'C24 H22 N2 O2'
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.781(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8659(4)
_cell_length_b                   9.3188(3)
_cell_length_c                   14.7114(5)
_cell_measurement_reflns_used    5250
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5030
_cell_measurement_theta_min      4.7310
_cell_volume                     1873.28(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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    -55.00  34.00   1.00    1.00    --  -40.46  37.00  90.00   89
  2  \w    -65.00  36.00   1.00    1.00    --  -40.46  37.00   0.00  101
  3  \w     11.00  37.00   1.00    1.00    --   40.46 -99.00 150.00   26
  4  \w     33.00  92.00   1.00    1.00    --  107.48 -94.00  30.00   59
  5  \w     61.00  95.00   1.00    1.00    --   40.46-125.00 -30.00   34
  6  \w    100.00 161.00   1.00    1.00    --  107.48  45.00 -30.00   61
  7  \w     93.00 177.00   1.00    1.00    --  107.48  77.00-180.00   84
  8  \w     65.00 137.00   1.00    1.00    --  107.48 178.00   0.00   72
  9  \w     65.00 151.00   1.00    1.00    --  107.48 178.00  90.00   86
 10  \w     81.00 170.00   1.00    1.00    --  107.48  45.00  90.00   89
;
_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      -0.0353312000
_diffrn_orient_matrix_UB_12      0.1562879000
_diffrn_orient_matrix_UB_13      0.0034498000
_diffrn_orient_matrix_UB_21      -0.0737539000
_diffrn_orient_matrix_UB_22      -0.0245624000
_diffrn_orient_matrix_UB_23      -0.0894785000
_diffrn_orient_matrix_UB_31      -0.0774958000
_diffrn_orient_matrix_UB_32      -0.0480774000
_diffrn_orient_matrix_UB_33      0.0573145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7326
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.610
_diffrn_reflns_theta_min         4.051
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82508
_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            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0542P)^2^+0.6648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3414
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02256e1.cif
_cod_data_source_block           exp_579
_cod_database_code               7120273
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.889
_reflns_odcompleteness_completeness 99.89
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C3(H3), C5(H5), C13(H13), C4(H4), C22(H22), C11(H11),
 C12(H12), C18(H18), C20(H20), C21(H21), C19(H19)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_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 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.646