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_7128500
_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         'C16 H10 Cl N O S'
_chemical_formula_sum            'C16 H10 Cl N O S'
_chemical_formula_weight         299.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-01-29
_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                 117.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.554(2)
_cell_length_b                   25.682(4)
_cell_length_c                   7.4204(18)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.9220
_cell_measurement_theta_min      6.7950
_cell_volume                     1277.3(6)
_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      150.0(2)
_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     45.00 102.00   1.00    2.00    --   25.57  57.00  60.00   57
  2  \w     60.00 112.00   1.00    2.00    --   25.57-178.00  90.00   52
  3  \w    -10.00  38.00   1.00    2.00    --   25.57  57.00  60.00   48
  4  \w     58.00 150.00   1.00   28.00    --   66.78 178.00-150.00   92
  5  \w    101.00 141.00   1.00   28.00    --   66.78 111.00 -30.00   40
  6  \w     69.00 136.00   1.00   28.00    --   66.78  61.00 -90.00   67
  7  \w     -7.00  51.00   1.00   28.00    --   66.78 -77.00 150.00   58
  8  \w     61.00 142.00   1.00   28.00    --   66.78  45.00 -30.00   81
  9  \w     68.00 107.00   1.00   28.00    --   66.78 -77.00 150.00   39
 10  \w    152.00 178.00   1.00   32.50    --  108.00 104.00 150.00   26
 11  \w     72.00 167.00   1.00   32.50    --  108.00  54.00 120.00   95
 12  \w     68.00 102.00   1.00   32.50    --  108.00  43.00-120.00   34
 13  \w     70.00 110.00   1.00   32.50    --  108.00-104.00 -90.00   40
 14  \w     23.00  49.00   1.00   32.50    --  108.00-104.00 -90.00   26
 15  \w     79.00 106.00   1.00   32.50    --  108.00-104.00   0.00   27
 16  \w     41.00  94.00   1.00   32.50    --  108.00-104.00  90.00   53
 17  \w    110.00 143.00   1.00   32.50    --  108.00 104.00  60.00   33
 18  \w     78.00 178.00   1.00   32.50    --  108.00  65.00-180.00  100
 19  \w    118.00 164.00   1.00   32.50    --  108.00  43.00-120.00   46
 20  \w     35.00 115.00   1.00   32.50    --  108.00 -65.00 -90.00   80
;
_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      -0.0275539000
_diffrn_orient_matrix_UB_12      0.0595667000
_diffrn_orient_matrix_UB_13      -0.0001041000
_diffrn_orient_matrix_UB_21      0.2279642000
_diffrn_orient_matrix_UB_22      0.0070445000
_diffrn_orient_matrix_UB_23      0.1185537000
_diffrn_orient_matrix_UB_31      0.0112387000
_diffrn_orient_matrix_UB_32      0.0042133000
_diffrn_orient_matrix_UB_33      -0.2011663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1237
_diffrn_reflns_av_unetI/netI     0.1182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3625
_diffrn_reflns_theta_full        66.88
_diffrn_reflns_theta_max         66.88
_diffrn_reflns_theta_min         6.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.399
_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    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.890
_refine_diff_density_min         -1.546
_refine_diff_density_rms         0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0936
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1858P)^2^+0.6384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2445
_refine_ls_wR_factor_ref         0.3183
_reflns_number_gt                1343
_reflns_number_total             2080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc02817k2.cif
_cod_data_source_block           v10cho2_lt_cu
_cod_original_cell_volume        1277.3(5)
_cod_database_code               7128500
_chemical_oxdiff_formula         'C64 H40 Cl4 N4 O4 S4'
_reflns_odcompleteness_completeness 95.48
_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), C14(H14), C11(H11), C5(H5), C12(H12), C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2021-01-27
_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 3.044
_oxdiff_exptl_absorpt_empirical_full_min 0.517