Cp*Co(III)-catalyzed thiocarbamate directed C−H aminocarbonyl-ation, amination, and cascade annulation of pyrroles
Saha, Shuvendu; Maji, Modhu Sudan; Chemical Communications  (2022) –; doi:10.1039/D2CC03992C

data_7130620
_publ_section_title
;
 Cp*Co(III)-catalyzed thiocarbamate directed C&#x2212;H
 aminocarbonyl-ation, amination, and cascade annulation of pyrroles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03992C
_journal_year                    2022
_chemical_formula_moiety         'C14 H15 N3 O S'
_chemical_formula_sum            'C14 H15 N3 O S'
_chemical_formula_weight         273.35
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-01
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-01-02 deposited with the CCDC.	2022-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                81.503(6)
_cell_angle_beta                 82.539(7)
_cell_angle_gamma                82.743(6)
_cell_formula_units_Z            4
_cell_length_a                   9.1959(7)
_cell_length_b                   9.4051(6)
_cell_length_c                   17.0462(15)
_cell_measurement_reflns_used    2356
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.2480
_cell_measurement_theta_min      2.1870
_cell_volume                     1437.12(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.870
_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     -0.34 119.66   0.50    6.00    --   28.00  59.94 -20.34  240
  2  \w     -0.34 119.66   0.50    6.00    --   28.00  59.94  69.66  240
  3  \w    -56.34  63.66   0.50    6.00    --  -28.00  59.94 159.66  240
  4  \w    -56.34  63.66   0.50    6.00    --  -28.00  59.94-110.34  240
  5  \f    -20.34 159.66   1.00    6.00 -20.34   0.00  59.94    --   180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0370467000
_diffrn_orient_matrix_UB_12      0.0575850000
_diffrn_orient_matrix_UB_13      -0.0219618000
_diffrn_orient_matrix_UB_21      0.0553068000
_diffrn_orient_matrix_UB_22      -0.0506824000
_diffrn_orient_matrix_UB_23      -0.0161780000
_diffrn_orient_matrix_UB_31      -0.0411494000
_diffrn_orient_matrix_UB_32      -0.0003376000
_diffrn_orient_matrix_UB_33      -0.0323890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31250
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.498
_diffrn_reflns_theta_min         2.203
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         12300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.0679
_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^)+(0.0564P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.2289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3637
_reflns_number_total             12300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03992c2.cif
_cod_data_source_block           SSH_842
_cod_database_code               7130620
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C25(H25), C2(H2A), C11(H11), C24(H24), C21(H21), C3(H3),
 C4(H4), C17(H17), C23(H23), C22(H22), C7(H7), C10(H10), C15(H15), C16(H16),
 C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C14(H14A,H14B,
 H14C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              9407
_shelx_hkl_checksum              63779
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.626
_oxdiff_exptl_absorpt_empirical_full_min 0.252