Cu(OTf)2-Catalyzed Access to 2,4,5-Trisubstituted Imidazoles from Acyclic Reissert Compounds
Sathyendran, Swetha; Moorthi, Vikraman Ganesh; Nokku, Sharmila; Joel, Aron Manick; Chandrasekaran, Suryanarayanan; Lin, Wei-Yu; Senadi, Gopal Chandru; Chemical Communications  (2026) –; doi:10.1039/D6CC00157B

data_7135753
_publ_section_title
;
 Cu(OTf)<sub>2</sub>-catalyzed access to 2,4,5-trisubstituted imidazoles
 from acyclic Reissert compounds.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9754
_journal_page_last               9758
_journal_paper_doi               10.1039/d6cc00157b
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C22 H13 F3 N2 O'
_chemical_formula_sum            'C22 H13 F3 N2 O'
_chemical_formula_weight         378.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-12-22 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.101(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3531(4)
_cell_length_b                   6.3271(2)
_cell_length_c                   26.0541(5)
_cell_measurement_reflns_used    10156
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.9190
_cell_measurement_theta_min      2.0000
_cell_volume                     3355.14(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -15.00 100.00   0.50   46.24    --   10.60  77.00-150.00  230
  2  \w   -100.00  79.00   0.50   46.24    --  -10.90  19.00-150.00  358
  3  \w    -36.00  79.00   0.50   46.24    --  -10.90  77.00-120.00  230
  4  \w    -79.00  38.00   0.50   46.24    --   10.60 -82.00   0.00  234
  5  \w   -100.00 -27.00   0.50   46.24    --  -10.90 -82.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0208879000
_diffrn_orient_matrix_UB_12      -0.0206613000
_diffrn_orient_matrix_UB_13      -0.0211762000
_diffrn_orient_matrix_UB_21      -0.0278348000
_diffrn_orient_matrix_UB_22      -0.0089386000
_diffrn_orient_matrix_UB_23      -0.0162658000
_diffrn_orient_matrix_UB_31      0.0016586000
_diffrn_orient_matrix_UB_32      0.1098475000
_diffrn_orient_matrix_UB_33      -0.0053000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15134
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.563
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0006(2)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0480P)^2^+1.7985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2608
_reflns_number_total             2937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00157b2.cif
_cod_data_source_block           k11211-jjw-a_auto
_cod_depositor_comments          'Adding full bibliography for 7135753.cif.'
_cod_database_code               7135753
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C15(H15), C2(H2), C22(H22), C14(H14), C11(H11), C18(H18),
 C21(H21), C13(H13), C12(H12), C19(H19), C20(H20)
;
_shelx_res_checksum              35707
_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 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.592