Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular reactions of β-CCl3-enones or β-CCl3-β-hydroxy ketones with various nucleophiles in CF3SO3H
Sokolov, Vladislav A.; Bakulina, Olga; Boyarskaya, Irina A.; Spiridonova, Dar'ya V.; Kryukova, Mariya A.; Vasilyev, Aleksander; New Journal of Chemistry  (2026) –; doi:10.1039/D5NJ03928B

data_7064192
_publ_section_title
;
 Synthesis of CCl3-substituted amides, ketones, indenes by intermolecular
 reactions of \b-CCl3-enones or \b-CCl3-\b-hydroxy ketones with various
 nucleophiles in CF3SO3H
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03928B
_journal_year                    2026
_chemical_formula_moiety         'C12 H11 Cl4 N O2'
_chemical_formula_sum            'C12 H11 Cl4 N O2'
_chemical_formula_weight         343.02
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-09-26 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.902(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9375(4)
_cell_length_b                   13.5556(3)
_cell_length_c                   9.6733(3)
_cell_measurement_reflns_used    7362
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.1350
_cell_measurement_theta_min      4.0100
_cell_volume                     1441.94(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.975
_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   -109.00 -53.00   0.50    1.00    --  -47.38 -73.00  61.00  112
  2  \w    -67.00  21.00   0.50    1.00    --  -47.38  73.00-169.00  176
  3  \w    -18.00  63.00   0.50    1.00    --   47.38 -73.00  61.00  162
  4  \w    -93.00 -40.00   0.50    4.00    -- -106.00  73.00-169.00  106
  5  \w   -155.00-130.00   0.50    4.00    -- -106.00 -73.00  61.00   50
  6  \w     43.00  79.00   0.50    4.00    --  113.25 -73.00  61.00   72
  7  \w    105.00 172.00   0.50    4.00    --  113.25  73.00-169.00  134
  8  \w   -104.00 -73.00   0.50    1.00    --  -47.38-125.00-150.00   62
  9  \w     75.00 107.00   0.50    1.00    --   47.38 125.00  90.00   64
 10  \w   -126.00 -94.00   0.50    4.00    -- -106.00 -30.00   0.00   64
 11  \w    -70.00 -39.00   0.50    4.00    -- -106.00  61.00 -90.00   62
 12  \w   -163.00 -99.00   0.50    4.00    -- -106.00 -45.00 150.00  128
 13  \w   -175.00 -94.00   0.50    4.00    -- -106.00 -45.00 120.00  162
 14  \w    -71.00 -45.00   0.50    4.00    -- -106.00  61.00  30.00   52
 15  \w    -71.00 -33.00   0.50    4.00    -- -106.00  61.00-120.00   76
 16  \w    -63.00 -35.00   0.50    4.00    -- -106.00  61.00 -30.00   56
 17  \w    -67.00 -38.00   0.50    4.00    -- -106.00  61.00 -60.00   58
 18  \w   -173.00-140.00   0.50    4.00    -- -106.00 -30.00   0.00   66
 19  \w     43.00  69.00   0.50    4.00    --  113.25 -61.00 150.00   52
 20  \w     45.00  70.00   0.50    4.00    --  113.25 -61.00  90.00   50
 21  \w     43.00  71.00   0.50    4.00    --  113.25 -61.00 -60.00   56
 22  \w     50.00  78.00   0.50    4.00    --  113.25 -77.00  90.00   56
 23  \w    116.00 146.00   0.50    4.00    --  113.25  30.00 -60.00   60
 24  \w     46.00  90.00   0.50    4.00    --  113.25 -94.00  30.00   88
 25  \w     68.00 104.00   0.50    4.00    --  113.25 -94.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0686278000
_diffrn_orient_matrix_UB_12      -0.0680963000
_diffrn_orient_matrix_UB_13      -0.0679517000
_diffrn_orient_matrix_UB_21      -0.0900966000
_diffrn_orient_matrix_UB_22      0.0276462000
_diffrn_orient_matrix_UB_23      -0.1590447000
_diffrn_orient_matrix_UB_31      0.0824540000
_diffrn_orient_matrix_UB_32      0.0866361000
_diffrn_orient_matrix_UB_33      -0.0027635000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8531
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         4.020
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0880P)^2^+0.1886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2530
_reflns_number_total             2661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           25387_skm191
_cod_database_code               7064192
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H11 Cl4 N O2'
_shelx_estimated_absorpt_t_max   0.707
_shelx_estimated_absorpt_t_min   0.523
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.553