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_7128497
_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_formula_moiety         'C19 H11 N O'
_chemical_formula_sum            'C19 H11 N O'
_chemical_formula_weight         269.29
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-01-18
_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                 92.560(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9273(11)
_cell_length_b                   7.8721(11)
_cell_length_c                   23.101(2)
_cell_measurement_reflns_used    901
_cell_measurement_temperature    150.01(13)
_cell_measurement_theta_max      66.6610
_cell_measurement_theta_min      5.6500
_cell_volume                     1258.5(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -13.00  97.00   1.00    1.00    --   25.51  57.00   0.00  110
  2  \w     36.00  63.00   1.00    1.00    --   25.51 -99.00-180.00   27
  3  \w    -10.00  64.00   1.00    1.00    --   25.51 -57.00-180.00   74
  4  \w     34.00 106.00   1.00    3.00    --   66.75  61.00 -60.00   72
  5  \w    103.00 128.00   1.00    3.00    --   66.75 111.00 150.00   25
  6  \w    100.00 150.00   1.00    3.00    --   66.75 111.00   0.00   50
  7  \w     36.00 146.00   1.00    3.00    --   66.75  45.00   0.00  110
  8  \w     12.00 106.00   1.00    3.00    --   66.75-111.00 120.00   94
  9  \w    122.00 176.00   1.00    3.50    --  108.00 104.00 -90.00   54
 10  \w     24.00  62.00   1.00    3.50    --  108.00-104.00  90.00   38
 11  \w     77.00 178.00   1.00    3.50    --  108.00  32.00 -60.00  101
 12  \w     77.00 117.00   1.00    3.50    --  108.00  54.00-120.00   40
 13  \w     67.00 101.00   1.00    3.50    --  108.00-104.00  90.00   34
 14  \w     26.00  59.00   1.00    3.50    --  108.00-104.00 150.00   33
 15  \w     63.00 110.00   1.00    3.50    --  108.00-104.00 150.00   47
 16  \w     31.00 126.00   1.00    3.50    --  108.00 -65.00 150.00   95
 17  \w    132.00 178.00   1.00    3.50    --  108.00  54.00-120.00   46
 18  \w     24.00  73.00   1.00    3.50    --  108.00-104.00 120.00   49
 19  \w    125.00 177.00   1.00    3.50    --  108.00  65.00 -30.00   52
;
_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      0.1983792000
_diffrn_orient_matrix_UB_12      0.0339427000
_diffrn_orient_matrix_UB_13      -0.0254174000
_diffrn_orient_matrix_UB_21      -0.1014599000
_diffrn_orient_matrix_UB_22      0.0652405000
_diffrn_orient_matrix_UB_23      -0.0563939000
_diffrn_orient_matrix_UB_31      -0.0005024000
_diffrn_orient_matrix_UB_32      0.1811417000
_diffrn_orient_matrix_UB_33      0.0251121000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1009
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            2604
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.702
_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    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0886
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2821
_reflns_number_gt                645
_reflns_number_total             1534
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc02817k2.cif
_cod_data_source_block           pab_yo_04_lt_cu
_cod_database_code               7128497
_chemical_oxdiff_formula         'C76 H44 N4 O4'
_reflns_odcompleteness_completeness 97.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C4(H4), C16(H16), C18(H18), C5(H5), C7(H7), C2(H2),
 C3(H3), C14(H14), C15(H15)
;
_olex2_date_sample_data_collection 2021-01-16
_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 89.931
_oxdiff_exptl_absorpt_empirical_full_min 0.418