An efficient direct electrolysis method for the synthesis of 1,1,1,3,3,3-hexafluoroisopropyxy substituted imidazo[1,2-<i>a</i>]pyridines.
Kong, Yanyan; Gong, Ming; Xu, Xuemei; Wu, Yangjie; Jiang, Xingmao; Organic & biomolecular chemistry 23 (2025) 2190–2194; doi:10.1039/d4ob02073a

data_7160340
_publ_section_title
;
 An efficient direct electrolysis method for the synthesis of
 1,1,1,3,3,3-hexafluoroisopropyxy substituted
 imidazo[1,2-<i>a</i>]pyridines.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2190
_journal_page_last               2194
_journal_paper_doi               10.1039/d4ob02073a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H10 F6 N2 O'
_chemical_formula_sum            'C16 H10 F6 N2 O'
_chemical_formula_weight         360.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-12-22 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4804(2)
_cell_length_b                   10.7171(3)
_cell_length_c                   14.9246(5)
_cell_measurement_reflns_used    1517
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.3020
_cell_measurement_theta_min      5.0590
_cell_volume                     1516.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -32.00  -6.00   1.00    1.00    --  -33.50 -77.00-120.00   26
  2  \w    -28.00  10.00   1.00    1.00    --  -33.50  19.00 -30.00   38
  3  \w   -102.00 -57.00   1.00    1.00    --  -33.50 -77.00-120.00   45
  4  \w     60.00  92.00   1.00    1.00    --   36.47  57.00-180.00   32
  5  \w     84.00 110.00   1.00    1.00    --   36.47 178.00  30.00   26
  6  \w     59.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   51
  7  \w     45.00  90.00   1.00    2.00    --  108.00 -94.00  60.00   45
  8  \w    100.00 158.00   1.00    2.00    --  108.00 111.00 -60.00   58
  9  \w     89.00 135.00   1.00    2.00    --  108.00  45.00 -90.00   46
 10  \w     45.00 116.00   1.00    2.00    --  108.00 -30.00  30.00   71
 11  \w     54.00 109.00   1.00    2.00    --  108.00 -94.00-150.00   55
 12  \w    111.00 162.00   1.00    2.00    --  108.00 111.00 150.00   51
 13  \w    -76.00 -50.00   1.00    1.00    --  -33.50 -77.00  90.00   26
 14  \w    -92.00 -67.00   1.00    1.00    --  -33.50 -57.00 -30.00   25
 15  \w    -32.00  27.00   1.00    1.00    --   36.47 -77.00-120.00   59
 16  \w     -3.00  54.00   1.00    1.00    --   36.47 -99.00 -30.00   57
 17  \w    119.00 145.00   1.00    2.00    --  108.00 178.00  30.00   26
 18  \w     37.00  64.00   1.00    2.00    --  108.00 -30.00 -60.00   27
 19  \w    147.00 173.00   1.00    2.00    --  108.00  61.00-150.00   26
 20  \w     89.00 115.00   1.00    2.00    --  108.00  61.00-150.00   26
 21  \w     76.00 102.00   1.00    2.00    --  108.00 -30.00 -60.00   26
 22  \w     48.00 103.00   1.00    2.00    --  108.00 -94.00 120.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105671000
_diffrn_orient_matrix_UB_12      0.1427718000
_diffrn_orient_matrix_UB_13      -0.0097036000
_diffrn_orient_matrix_UB_21      0.0317074000
_diffrn_orient_matrix_UB_22      -0.0115250000
_diffrn_orient_matrix_UB_23      -0.1008490000
_diffrn_orient_matrix_UB_31      -0.1591343000
_diffrn_orient_matrix_UB_32      -0.0118491000
_diffrn_orient_matrix_UB_33      -0.0194873000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5527
_diffrn_reflns_point_group_measured_fraction_full 0.729
_diffrn_reflns_point_group_measured_fraction_max 0.713
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.716
_diffrn_reflns_theta_min         5.081
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0602P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.383
_reflns_Friedel_fraction_full    0.434
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                1743
_reflns_number_total             2085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02073a2.cif
_cod_data_source_block           202111300
_cod_depositor_comments          'Adding full bibliography for 7160340.cif.'
_cod_original_cell_volume        1516.37(8)
_cod_database_code               7160340
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3N1O4Br1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              95310
_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.889