An HFIP-assisted, cobalt-catalyzed three-component electrophilic C-H amination/cyclization/directing group removal cascade to naphtho[1,2-d]imidazoles.
Begam, Hasina Mamataj; Pradhan, Kangkan; Varalaxmi, Kasarla; Jana, Ranjan; Chemical communications (Cambridge, England) 59 (2023) 5595–5598; doi:10.1039/d3cc00749a

data_7131555
_publ_section_title
;
 An HFIP-assisted, cobalt-catalyzed three-component electrophilic C-H
 amination/cyclization/directing group removal cascade to
 naphtho[1,2-d]imidazoles.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5595
_journal_page_last               5598
_journal_paper_doi               10.1039/d3cc00749a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C17 H18 N2'
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33
_chemical_name_systematic        monoclinic
_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     dual
_audit_creation_date             2022-05-11
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-21 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.428(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2417(9)
_cell_length_b                   12.7619(9)
_cell_length_c                   7.8090(5)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.48
_cell_measurement_theta_min      3.46
_cell_volume                     1301.81(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-III 8D VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25331
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.480
_diffrn_reflns_theta_min         4.844
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1735 before and 0.1122 after correction.
The Ratio of minimum to maximum transmission is 0.4340.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.062(7)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0672
_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^)+(0.1260P)^2^+0.3059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1802
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             2532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00749a2.cif
_cod_data_source_block           f
_cod_depositor_comments
'Adding full bibliography for 7131554--7131555.cif.'
_cod_database_code               7131555
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C8(H8), C4(H4), C7(H7), C6(H6), C5(H5)
;
_shelx_res_checksum              95868
_shelx_hkl_checksum              921
_olex2_submission_special_instructions 'No special instructions were received'