Copper-catalyzed four-component radical cascade cyclization of enynes to assemble trifluoromethyl- and carbamoyloxyl-substituted pyrrolo[1,2-<i>a</i>]benzimidazoles.
Liu, Lixin; Liu, Min; Wang, Qian; Liu, Bifu; Feng, Kejun; Organic & biomolecular chemistry 24 (2026) 1418–1423; doi:10.1039/d5ob01924a

data_7160997
_publ_section_title
;
 Copper-catalyzed four-component radical cascade cyclization of enynes to
 assemble trifluoromethyl- and carbamoyloxyl-substituted
 pyrrolo[1,2-<i>a</i>]benzimidazoles.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1418
_journal_page_last               1423
_journal_paper_doi               10.1039/d5ob01924a
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C25 H25 Cl F3 N3 O2'
_chemical_formula_sum            'C25 H25 Cl F3 N3 O2'
_chemical_formula_weight         491.93
_chemical_name_systematic
'(Z)-(4-chlorophenyl)(2-methyl-2-(2,2,2-trifluoroethyl)-1,2-dihydro-3H-benzo[d]pyrrolo[1 ,2-a]imidazol-3-ylidene)methyl diethylcarbamate'
_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_block_doi                 10.5517/ccdc.csd.cc2pjsz0
_audit_creation_date             2026-01-21
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-21 deposited with the CCDC.	2026-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                97.350(6)
_cell_angle_beta                 96.784(6)
_cell_angle_gamma                91.666(6)
_cell_formula_units_Z            2
_cell_length_a                   7.1709(5)
_cell_length_b                   8.8883(7)
_cell_length_c                   19.2532(15)
_cell_measurement_reflns_used    2920
_cell_measurement_temperature    300
_cell_measurement_theta_max      23.0250
_cell_measurement_theta_min      2.3720
_cell_volume                     1207.32(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00 120.00   1.00   16.00    --   30.00  54.00   0.00  180
  2  \w    -60.00 120.00   1.00   16.00    --   30.00  54.00 120.00  180
  3  \w    -60.00 120.00   1.00   16.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0640500000
_diffrn_orient_matrix_UB_12      0.0375278000
_diffrn_orient_matrix_UB_13      0.0282154000
_diffrn_orient_matrix_UB_21      0.0459697000
_diffrn_orient_matrix_UB_22      0.0366869000
_diffrn_orient_matrix_UB_23      -0.0243003000
_diffrn_orient_matrix_UB_31      -0.0610468000
_diffrn_orient_matrix_UB_32      0.0610989000
_diffrn_orient_matrix_UB_33      0.0037908000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.1440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.617
_diffrn_reflns_theta_min         2.418
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         8106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.2525
_refine_ls_R_factor_gt           0.0704
_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^)+(0.0495P)^2^+0.0113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2590
_reflns_number_total             8106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01924a2.cif
_cod_data_source_block           llx
_cod_database_code               7160997
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.959
_diffrn_oxdiff_ac3_digest_hkl    411574a5760b8a22b466a2b9a2f1f668c89ed1
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B), C2(H2A,H2B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C21(H21), C22(H22), C10(H10), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              42239
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.930