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_1566805
_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         'C23 H17 N3'
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.41
_chemical_melting_point          414
_chemical_name_common
3-benzyl-2-(pyridin-2-yl)-3H-naphtho[1,2-d]imidazole
_chemical_properties_physical    Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-09
_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                 90.457(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8246(5)
_cell_length_b                   8.7668(4)
_cell_length_c                   16.2183(7)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    298
_cell_measurement_theta_max      66.522
_cell_measurement_theta_min      5.455
_cell_volume                     1681.20(13)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_measured_fraction_theta_max 0.9875
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16494
_diffrn_reflns_theta_full        66.6097
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         5.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1419 before and 0.0939 after correction. The Ratio of minimum to maximum transmission is 0.7699. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3251
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             706.0166
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethne, petroleum ether'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.2797
_refine_diff_density_min         -0.3376
_refine_diff_density_rms         0.0865
_refine_ls_d_res_high            0.8399
_refine_ls_d_res_low             8.1089
_refine_ls_goodness_of_fit_ref   1.0730
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0730
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+1.2123P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -14
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -10
_reflns_number_gt                2724
_reflns_number_total             2930
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc01420c2.cif
_cod_data_source_block           K_101_0m_a
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               1566805
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00I(H00I), C00H(H00H), C00K(H00K), C00B(H00B), C00N(H00N),
 C00A(H00A), C00F(H00F), C00G(H00G), C00L(H00L), C00J(H00J), C00O(H00O),
 C00Q(H00Q), C00P(H00P), C00M(H00M)
;
_olex2_submission_special_instructions 'No special instructions were received'