Harnessing Sulfur and Nitrogen in the Cobalt (III)-Catalyzed Unsymmetrical Double Annulation of Thioamides: Probing the Origin of Chemo- and Regioselectivity
Shankar, Majji; Saha, Arijit; Sau, Somratan; Ghosh, Arghadip; Gandon, Vincent; Sahoo, Akhila Kumar; Chemical Science  (2021) –; doi:10.1039/D1SC00765C

data_1561174
_publ_section_title
;
 Harnessing Sulfur and Nitrogen in the Cobalt (III)-Catalyzed
 Unsymmetrical Double Annulation of Thioamides: Probing the Origin of
 Chemo- and Regioselectivity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC00765C
_journal_year                    2021
_chemical_formula_moiety         'C37 H21 Cl4 N O2 S'
_chemical_formula_sum            'C37 H21 Cl4 N O2 S'
_chemical_formula_weight         685.41
_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
_audit_creation_date             2020-11-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                70.572(4)
_cell_angle_beta                 83.642(3)
_cell_angle_gamma                86.486(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0387(7)
_cell_length_b                   12.2872(11)
_cell_length_c                   15.4499(13)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.59
_cell_volume                     1607.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            67192
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_min         2.268
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6964
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0792 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.9340. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.404
_refine_diff_density_min         -1.262
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         7393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1180P)^2^+2.3646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5708
_reflns_number_total             7393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00765c3.cif
_cod_data_source_block           aks230_0m_a
_cod_database_code               1561174
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.868
_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. Others
 Fixed Sof: N1(0.5) N2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00N(H00N), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00U(H00U), C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010),
 C011(H011), C013(H013), C014(H014), C015(H015), C016(H016), C017(H017)
3.b Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C)
;
_shelx_res_checksum              10824
_shelx_hkl_checksum              92534
_olex2_submission_special_instructions 'No special instructions were received'