Divergent Annulative C–C Coupling of Indoles Initiated by Manganese-Catalyzed C–H Activation
Liu, Bingxian; Li, Jie; Hu, Panjie; Zhou, Xukai; Bai, Dachang; Li, Xingwei; ACS Catalysis 8 (2018) 9463–; doi:10.1021/acscatal.8b02560

data_4515553
_publ_section_title
;
 Divergent Annulative C--C Coupling of Indoles Initiated by
 Manganese-Catalyzed C--H Activation
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9463
_journal_paper_doi               10.1021/acscatal.8b02560
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C24 H22 Cl N3 O2'
_chemical_formula_sum            'C24 H22 Cl N3 O2'
_chemical_formula_weight         419.89
_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   geom
_audit_creation_date             2018-06-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                104.256(2)
_cell_angle_beta                 109.363(2)
_cell_angle_gamma                106.026(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5004(3)
_cell_length_b                   11.2780(4)
_cell_length_c                   11.5979(3)
_cell_measurement_reflns_used    10193
_cell_measurement_temperature    296.6(5)
_cell_measurement_theta_max      72.1720
_cell_measurement_theta_min      4.3410
_cell_volume                     1045.71(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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   -103.00  -9.00   1.00    1.00    --  -35.60 -77.00  30.00   94
  2  \w      6.00 107.00   1.00    1.00    --   35.60  19.00-120.00  101
  3  \w     23.00  89.00   1.00    1.00    --   35.60-125.00  90.00   66
  4  \w     -8.00  70.00   1.00    1.00    --   35.60 -91.00 150.00   78
  5  \w     17.00 105.00   1.00    1.00    --   35.60  38.00 -30.00   88
  6  \w    -32.00  62.00   1.00    1.00    --   35.60 -77.00  60.00   94
  7  \w      1.00  75.00   1.00    1.00    --   35.60 -99.00-180.00   74
  8  \w     17.00 105.00   1.00    1.00    --   35.60  38.00  30.00   88
  9  \w      6.00 107.00   1.00    1.00    --   35.60  19.00 -60.00  101
 10  \w      9.00 103.00   1.00    1.00    --   35.60  77.00 -30.00   94
 11  \w     17.00 105.00   1.00    1.00    --   35.60  38.00-180.00   88
 12  \w     23.00  89.00   1.00    1.00    --   35.60-125.00   0.00   66
 13  \w    -32.00  52.00   1.00    1.00    --   35.60 -57.00   0.00   84
 14  \w     19.00 103.00   1.00    1.00    --   35.60  57.00 -90.00   84
 15  \w     39.00 130.00   1.00    1.00    --  108.69 -30.00-120.00   91
 16  \w     39.00 109.00   1.00    1.00    --  108.69 -95.00 -60.00   70
 17  \w     39.00 112.00   1.00    1.00    --  108.69-111.00-150.00   73
 18  \w    100.00 178.00   1.00    1.00    --  108.69 111.00 120.00   78
 19  \w     39.00 109.00   1.00    1.00    --  108.69 -95.00  30.00   70
 20  \w     39.00 109.00   1.00    1.00    --  108.69 -95.00  60.00   70
 21  \w     40.00 126.00   1.00    1.00    --  108.69 -45.00 -30.00   86
 22  \w     42.00 127.00   1.00    1.00    --  108.69 -61.00  60.00   85
 23  \w     57.00 151.00   1.00    1.00    --  108.69 178.00   0.00   94
 24  \w    100.00 178.00   1.00    1.00    --  108.69 111.00-150.00   78
 25  \w     87.00 178.00   1.00    1.00    --  108.69  30.00-150.00   91
 26  \w     39.00 112.00   1.00    1.00    --  108.69-111.00 -90.00   73
 27  \w     40.00 126.00   1.00    1.00    --  108.69 -45.00 150.00   86
 28  \w     37.00 147.00   1.00    1.00    --  108.69 -15.00  30.00  110
 29  \w     40.00 126.00   1.00    1.00    --  108.69 -45.00-120.00   86
 30  \w      9.00 103.00   1.00    1.00    --   35.60  77.00 120.00   94
 31  \w      9.00 103.00   1.00    1.00    --   35.60  77.00-180.00   94
 32  \w    -32.00  52.00   1.00    1.00    --   35.60 -57.00-150.00   84
 33  \w     19.00 103.00   1.00    1.00    --   35.60  57.00  90.00   84
 34  \w      9.00 103.00   1.00    1.00    --   35.60  77.00-120.00   94
 35  \w      9.00 103.00   1.00    1.00    --   35.60  77.00   0.00   94
 36  \w      1.00  75.00   1.00    1.00    --   35.60 -99.00 -90.00   74
 37  \w     19.00 103.00   1.00    1.00    --   35.60  57.00  30.00   84
 38  \w    -36.00  65.00   1.00    1.00    --   35.60 -19.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0843787000
_diffrn_orient_matrix_UB_12      -0.1302101000
_diffrn_orient_matrix_UB_13      -0.1218711000
_diffrn_orient_matrix_UB_21      -0.1328520000
_diffrn_orient_matrix_UB_22      0.0476769000
_diffrn_orient_matrix_UB_23      -0.0630595000
_diffrn_orient_matrix_UB_31      0.1005587000
_diffrn_orient_matrix_UB_32      0.0650050000
_diffrn_orient_matrix_UB_33      -0.0647175000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.245
_diffrn_reflns_theta_min         4.354
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1195P)^2^+0.3578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.1897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3704
_reflns_number_total             4049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02560_si_002.cif
_cod_data_source_block           lbx-10754
_cod_original_cell_volume        1045.71(6)
_cod_database_code               4515553
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
_shelx_estimated_absorpt_t_max   0.620
_shelx_estimated_absorpt_t_min   0.418
_reflns_odcompleteness_completeness 99.87
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C18(H18), C8(H8), C16(H16), C7(H7), C17(H17), C23(H23),
 C24(H24), C22(H22)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              67860
_shelx_hkl_checksum              44065
_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 4.861
_oxdiff_exptl_absorpt_empirical_full_min 0.536