C(sp2)-H Functionalization of Imidazole at C2 and C4-Position via Palladium-Catalyzed Isocyanide Insertion Leading to Indeno[1,2-d]imidazole and Imidazo[1,2-a]indole Derivatives.
Ren, Zhi-Lin; Cai, Shuang; Liu, Ying-Ying; Xie, Yin-Qing; Yuan, Ding; Lei, Min; He, Ping; Wang, Long; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01454

data_4038643
_publ_section_title
;
 C(sp2)-H Functionalization of Imidazole at C2 and C4-Position via
 Palladium-Catalyzed Isocyanide Insertion Leading to
 Indeno[1,2-d]imidazole and Imidazo[1,2-a]indole Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01454
_journal_year                    2020
_chemical_formula_moiety         'C21 H17 Cl F3 N3'
_chemical_formula_sum            'C21 H17 Cl F3 N3'
_chemical_formula_weight         403.83
_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             2020-05-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.821(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0093(9)
_cell_length_b                   13.7121(17)
_cell_length_c                   17.661(2)
_cell_measurement_reflns_used    1547
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      23.213
_cell_measurement_theta_min      2.793
_cell_volume                     1891.2(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.1607
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29708
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_min         2.365
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0806 before and 0.0757 after correction.
The Ratio of minimum to maximum transmission is 0.7221.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0759
_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^)+(0.0259P)^2^+4.2456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2335
_reflns_number_total             3855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01454_si_001.cif
_cod_data_source_block           mo_0526_1_0m
_cod_database_code               4038643
_shelx_shelxl_version_number     2018/3
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C10(H10), C13(H13), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              4945
_shelx_hkl_checksum              41282
_olex2_submission_special_instructions 'No special instructions were received'