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_4038642
_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         'C27 H23 Cl N4'
_chemical_formula_sum            'C27 H23 Cl N4'
_chemical_formula_weight         438.94
_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     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                75.052(2)
_cell_angle_beta                 81.967(2)
_cell_angle_gamma                79.048(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9037(3)
_cell_length_b                   10.4256(4)
_cell_length_c                   15.9906(7)
_cell_measurement_reflns_used    5186
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.345
_cell_measurement_theta_min      2.649
_cell_volume                     1086.72(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0679
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27428
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.049
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0667 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.7414.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0442P)^2^+0.3330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             4468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01454_si_002.cif
_cod_data_source_block           mo_0526_2_0m
_cod_database_code               4038642
_shelx_shelxl_version_number     2018/3
_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:
 C19(H19), C20(H20), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C17(H17A,H17B), C22(H22A,H22B), C25(H25A,
 H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C14(H14), C15(H15), C18(H18), C24(H24)
;
_shelx_res_checksum              64938
_shelx_hkl_checksum              98887
_olex2_submission_special_instructions 'No special instructions were received'