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_1566803
_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_formula_moiety         '0.11(C22 H22 N4 O)'
_chemical_formula_sum            'C2.44 H2.44 N0.44 O0.11'
_chemical_formula_weight         39.83
_chemical_melting_point          408
_chemical_name_common
3-cyclohexyl-1-(5-methylpyrazin-2-yl)-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one
_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     direct
_audit_creation_date             2020-07-06
_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                67.7270(10)
_cell_angle_beta                 89.0730(10)
_cell_angle_gamma                71.4000(10)
_cell_formula_units_Z            18
_cell_length_a                   7.9957(2)
_cell_length_b                   10.4307(2)
_cell_length_c                   12.5078(3)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.599
_cell_measurement_theta_min      3.846
_cell_volume                     908.36(4)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0634
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28821
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.701
_diffrn_reflns_theta_max         66.701
_diffrn_reflns_theta_min         3.846
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1243 before and 0.0796 after correction. The Ratio of minimum to maximum transmission is 0.8001. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0399P)^2^+0.3924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3086
_reflns_number_total             3182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01420c2.cif
_cod_data_source_block           hm_583_0m_a
_cod_database_code               1566803
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.842
_shelx_estimated_absorpt_t_min   0.621
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00E), C00J(H00I,H00J), C00N(H00L,H00N), C00P(H00P,H00Q), C00Q(H00R,
 H00S)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K),
 C00M(H00M), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00R(H00T,H00U,H00V)
;
_shelx_res_checksum              89551
_shelx_hkl_checksum              1684
_olex2_submission_special_instructions 'No special instructions were received'