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_7128499
_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         'C15 H8 Br N O'
_chemical_formula_sum            'C15 H8 Br N O'
_chemical_formula_weight         298.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-01-07
_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                   5.0630(7)
_cell_length_b                   6.0703(11)
_cell_length_c                   36.335(5)
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.9470
_cell_measurement_theta_min      2.4030
_cell_volume                     1116.7(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      150.00(10)
_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     80.00 115.00   1.00    1.50    --   25.44 178.00 -60.00   35
  2  \w    -10.00  88.00   1.00    1.50    --   25.44  57.00-150.00   98
  3  \w    112.00 143.00   1.00    7.50    --   66.72 111.00  90.00   31
  4  \w    115.00 148.00   1.00    7.50    --   66.72 178.00-150.00   33
  5  \w    101.00 137.00   1.00    7.50    --   66.72 111.00   0.00   36
  6  \w     39.00 146.00   1.00    7.50    --   66.72  30.00-180.00  107
  7  \w    134.00 178.00   1.00   12.50    --  108.00 104.00-120.00   44
  8  \w    125.00 178.00   1.00   12.50    --  108.00  54.00 -60.00   53
  9  \w     70.00 111.00   1.00   12.50    --  108.00-104.00  90.00   41
 10  \w     68.00 118.00   1.00   12.50    --  108.00  54.00 -60.00   50
 11  \w    132.00 171.00   1.00   12.50    --  108.00 104.00  60.00   39
 12  \w     81.00 125.00   1.00   12.50    --  108.00  65.00  30.00   44
 13  \w    129.00 175.00   1.00   12.50    --  108.00  65.00  30.00   46
 14  \w    106.00 178.00   1.00   12.50    --  108.00 104.00 -30.00   72
 15  \w     42.00  69.00   1.00   12.50    --  108.00-104.00  90.00   27
;
_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      0.0725012000
_diffrn_orient_matrix_UB_12      0.2127631000
_diffrn_orient_matrix_UB_13      -0.0208122000
_diffrn_orient_matrix_UB_21      -0.1789844000
_diffrn_orient_matrix_UB_22      0.1340077000
_diffrn_orient_matrix_UB_23      0.0259767000
_diffrn_orient_matrix_UB_31      0.2349753000
_diffrn_orient_matrix_UB_32      0.0364543000
_diffrn_orient_matrix_UB_33      0.0262160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            1897
_diffrn_reflns_theta_full        66.77
_diffrn_reflns_theta_max         66.77
_diffrn_reflns_theta_min         7.70
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.882
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.550
_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    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0553
_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^)+(0.1085P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1249
_reflns_number_total             1351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc02817k2.cif
_cod_data_source_block           pab_yo_02_lt_cu
_cod_database_code               7128499
_chemical_oxdiff_formula         'C60 H32 Br4 N4 O4'
_reflns_odcompleteness_completeness 93.77
_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:
 C12(H12), C14(H14), C4(H4), C11(H11), C5(H5), C2(H2), C7(H7), C3(H3)
;
_olex2_date_sample_data_collection 2021-01-06
_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 7.146
_oxdiff_exptl_absorpt_empirical_full_min 0.549