Directing group switch in copper-catalyzed electrophilic C–H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole
Begam, Hasina Mamataj; Nandi, Shantanu; Jana, Ranjan; Chemical Science  (2022) –; doi:10.1039/D2SC01420C

data_1566802
_publ_section_title
;
 Directing group switch in copper-catalyzed electrophilic C--H
 amination/migratory annulation cascade: divergent access to
 benzimidazolone/benzimidazole
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01420C
_journal_year                    2022
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C16 H12 N2 S'
_chemical_formula_sum            'C16 H12 N2 S'
_chemical_formula_weight         264.34
_chemical_melting_point          398
_chemical_name_common            HM
_chemical_name_systematic        HM-643S
_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
_audit_creation_date             2020-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1282(2)
_cell_length_b                   14.1422(4)
_cell_length_c                   14.4603(4)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.819
_cell_measurement_theta_min      4.382
_cell_volume                     1247.95(6)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19122
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.813
_diffrn_reflns_theta_max         66.813
_diffrn_reflns_theta_min         4.382
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.167
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1175 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.8791. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       chloroform
_exptl_crystal_F_000             552
_exptl_crystal_preparation       'in CHCl3'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.8469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2132
_reflns_number_total             2213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01420c2.cif
_cod_data_source_block           hm_643s_0m_a
_cod_database_code               1566802
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.671
_shelx_estimated_absorpt_t_min   0.671
_exptl_absorpt_special_details   Nothing
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
;
_shelx_res_checksum              15185
_shelx_hkl_checksum              31958
_olex2_submission_original_sample_id HM-643S
_olex2_submission_special_instructions 'No special instructions were received'