Cp*Co(III)-Catalyzed C−H Amination/Annulation Cascade of Sulfoxonium Ylides with Anthranils for the Synthesis of Indoloindolones
Aher, Yogesh N.; Pawar, Amit B.; Chemical Communications  (2021) –; doi:10.1039/D1CC02817K

data_7128498
_publ_section_title
;
 Cp*Co(III)-Catalyzed C&#x2212;H Amination/Annulation Cascade of
 Sulfoxonium Ylides with Anthranils for the Synthesis of Indoloindolones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC02817K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H10 Cl N O'
_chemical_formula_sum            'C16 H10 Cl N O'
_chemical_formula_weight         267.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-12-31
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.572(2)
_cell_length_b                   6.9489(7)
_cell_length_c                   7.4796(7)
_cell_measurement_reflns_used    611
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.5990
_cell_measurement_theta_min      6.3680
_cell_volume                     1277.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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     51.00  76.00   1.00    1.00    --   25.57 -99.00 -30.00   25
  2  \w      5.00  77.00   1.00    1.00    --   25.57 -99.00  30.00   72
  3  \w    -10.00  15.00   1.00    1.00    --   25.57  61.00-179.00   25
  4  \w     71.00  96.00   1.00    1.00    --   25.57  61.00-179.00   25
  5  \w      6.00  35.00   1.00    1.00    --   25.57 -99.00 -30.00   29
  6  \w     72.00 150.00   1.00    8.00    --   66.78  30.00  90.00   78
  7  \w    103.00 149.00   1.00    8.00    --   66.78 111.00  30.00   46
  8  \w     -3.00  70.00   1.00    8.00    --   66.78  30.00  90.00   73
  9  \w    100.00 130.00   1.00    8.00    --   66.78 111.00 -90.00   30
 10  \w    110.00 175.00   1.00   20.00    --  108.00 104.00 -30.00   65
 11  \w    137.00 163.00   1.00   20.00    --  108.00 104.00  60.00   26
 12  \w    118.00 150.00   1.00   20.00    --  108.00 -77.00 120.00   32
 13  \w     84.00 109.00   1.00   20.00    --  108.00 -77.00 120.00   25
 14  \w     25.00  65.00   1.00   20.00    --  108.00 -77.00 120.00   40
 15  \w     82.00 138.00   1.00   20.00    --  108.00  65.00 -90.00   56
 16  \w     33.00  94.00   1.00   20.00    --  108.00-104.00  90.00   61
 17  \w     86.00 142.00   1.00   20.00    --  108.00  54.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567932000
_diffrn_orient_matrix_UB_12      -0.0747296000
_diffrn_orient_matrix_UB_13      0.0524685000
_diffrn_orient_matrix_UB_21      0.0261604000
_diffrn_orient_matrix_UB_22      0.1381139000
_diffrn_orient_matrix_UB_23      -0.1362230000
_diffrn_orient_matrix_UB_31      0.0040666000
_diffrn_orient_matrix_UB_32      0.1568021000
_diffrn_orient_matrix_UB_33      0.1451788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2262
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         6.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.556
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1688P)^2^+0.7397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2889
_reflns_number_gt                832
_reflns_number_total             1484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc02817k2.cif
_cod_data_source_block           pab_yo_01_rt_cu
_cod_database_code               7128498
_chemical_oxdiff_formula         'C64 H40 Cl4 N4 O4'
_reflns_odcompleteness_completeness 97.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C12(H12), C14(H14), C11(H11), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2020-12-30
_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 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.804