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_7064194
_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         '2(C10 H8 Cl4 O)'
_chemical_formula_sum            'C20 H16 Cl8 O2'
_chemical_formula_weight         571.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-06
_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                 93.525(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2258(2)
_cell_length_b                   13.7660(3)
_cell_length_c                   15.1288(3)
_cell_measurement_reflns_used    10626
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      69.0700
_cell_measurement_theta_min      4.3310
_cell_volume                     2333.50(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (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 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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   -102.00 -66.00   0.50    0.73    --  -35.49 -40.00 152.00   72
  2  \w    -65.00 -39.00   0.50    0.73    --  -35.49 -40.00 152.00   52
  3  \w     11.00  52.00   0.50    0.73    --   35.49 -40.00 152.00   82
  4  \w     28.00  62.00   0.50    0.73    --   35.49  40.00 -54.00   68
  5  \w    130.00 156.00   0.50    2.90    --  100.00  40.00 -54.00   52
  6  \w     30.00 110.00   0.50    2.90    --  100.00 -40.00 152.00  160
  7  \w     -3.00  43.00   0.50    0.73    --  -35.49  11.00 -30.00   92
  8  \w    -11.00  34.00   0.50    0.73    --  -35.49  43.00-150.00   90
  9  \w    -80.00  -6.00   0.50    0.73    --  -35.49  11.00 -30.00  148
 10  \w    -55.00 -29.00   0.50    0.73    --  -35.49  43.00-150.00   52
 11  \w    -58.00 -15.00   0.50    0.73    --  -35.49 138.00 -60.00   86
 12  \w     -3.00  22.00   0.50    0.73    --  -35.49  40.00 -54.00   50
 13  \w    -87.00 -51.00   0.50    0.73    --  -35.49 138.00  30.00   72
 14  \w    -85.00 -60.00   0.50    0.73    --  -35.49 138.00 -60.00   50
 15  \w    -43.00 -14.00   0.50    0.73    --  -35.49 138.00  30.00   58
 16  \w    -27.00  22.00   0.50    0.73    --   35.49 -32.00  60.00   98
 17  \w     32.00  72.00   0.50    0.73    --   35.49-104.00   0.00   80
 18  \w     25.00  53.00   0.50    0.73    --   35.49 -32.00  60.00   56
 19  \w     74.00 106.00   0.50    0.73    --   35.49  32.00  60.00   64
 20  \w     40.00  70.00   0.50    0.73    --   35.49  32.00  60.00   60
 21  \w     78.00 103.00   0.50    0.73    --   35.49  43.00 -60.00   50
 22  \w     83.00 115.00   0.50    2.90    --  100.00  77.00 -90.00   64
 23  \w    119.00 146.00   0.50    2.90    --  100.00  37.00 -30.00   54
 24  \w    100.00 126.00   0.50    2.90    --  100.00  53.00 -30.00   52
 25  \w     88.00 120.00   0.50    2.90    --  100.00 -30.00 -30.00   64
 26  \w     28.00  83.00   0.50    2.90    --  100.00 -30.00 -30.00  110
 27  \w     26.00 106.00   0.50    2.90    --  100.00 -91.00  60.00  160
 28  \w     76.00 129.00   0.50    2.90    --  100.00-149.00  60.00  106
 29  \w     32.00 107.00   0.50    2.90    --  100.00-107.00  30.00  150
 30  \w     85.00 113.00   0.50    2.90    --  100.00  77.00 -30.00   56
 31  \w     56.00 104.00   0.50    2.90    --  100.00-107.00-120.00   96
 32  \w     86.00 112.00   0.50    2.90    --  100.00  37.00 -30.00   52
 33  \w     33.00 125.00   0.50    2.90    --  100.00 -61.00-180.00  184
 34  \w     77.00 128.00   0.50    2.90    --  100.00 -86.00-180.00  102
 35  \w     34.00  85.00   0.50    2.90    --  100.00-125.00-150.00  102
 36  \w    104.00 129.00   0.50    2.90    --  100.00  91.00-180.00   50
 37  \w     80.00 105.00   0.50    2.90    --  100.00-125.00 -30.00   50
 38  \w     26.00  78.00   0.50    2.90    --  100.00 -91.00 120.00  104
 39  \w     76.00 156.00   0.50    2.90    --  100.00  61.00-180.00  160
 40  \w    123.00 149.00   0.50    2.90    --  100.00  77.00 -90.00   52
 41  \w     43.00  74.00   0.50    2.90    --  100.00 -53.00 -90.00   62
 42  \w    129.00 157.00   0.50    2.90    --  100.00  53.00 -30.00   56
 43  \w     42.00  67.00   0.50    2.90    --  100.00 -86.00-180.00   50
 44  \w     39.00  64.00   0.50    2.90    --  100.00-149.00  60.00   50
 45  \w     51.00  76.00   0.50    2.90    --  100.00 -40.00 152.00   50
 46  \w    -40.00 -14.00   0.50    0.73    --  -35.49 138.00 -30.00   52
 47  \w    -71.00 -24.00   0.50    0.73    --  -35.49 104.00-120.00   94
 48  \w    -60.00 -34.00   0.50    0.73    --  -35.49 -54.00   0.00   52
 49  \w    -44.00  -9.00   0.50    0.73    --  -35.49  77.00 -60.00   70
 50  \w     10.00  35.00   0.50    0.73    --  -35.49  77.00 -60.00   50
 51  \w     10.00  65.00   0.50    0.73    --   35.49  65.00 150.00  110
 52  \w     14.00  69.00   0.50    0.73    --   35.49-104.00-150.00  110
 53  \w     19.00  45.00   0.50    0.73    --   35.49  43.00  90.00   52
 54  \w     27.00  53.00   0.50    0.73    --   35.49  43.00-180.00   52
 55  \w     26.00  53.00   0.50    0.73    --   35.49  54.00  90.00   54
 56  \w     10.00  79.00   0.50    0.73    --   35.49  65.00  90.00  138
 57  \w     49.00  74.00   0.50    0.73    --   35.49  65.00 120.00   50
 58  \w     78.00 103.00   0.50    0.73    --   35.49  54.00  90.00   50
 59  \w     18.00  43.00   0.50    0.73    --   35.49  65.00 120.00   50
 60  \w    117.00 155.00   0.50    2.90    --  100.00  37.00   0.00   76
 61  \w     75.00 117.00   0.50    2.90    --  100.00 -30.00  30.00   84
 62  \w    131.00 157.00   0.50    2.90    --  100.00  53.00 120.00   52
 63  \w     80.00 114.00   0.50    2.90    --  100.00  45.00   0.00   68
 64  \w    113.00 139.00   0.50    2.90    --  100.00  69.00  90.00   52
 65  \w     77.00 103.00   0.50    2.90    --  100.00  53.00 120.00   52
 66  \w    113.00 143.00   0.50    2.90    --  100.00  71.00   0.68   60
 67  \w     57.00 128.00   0.50    2.90    --  100.00 -22.00 120.00  142
 68  \w     93.00 152.00   0.50    2.90    --  100.00  30.00 -60.00  118
 69  \w     77.00 103.00   0.50    2.90    --  100.00  53.00  60.00   52
 70  \w     75.00 100.00   0.50    2.90    --  100.00  61.00   0.00   50
 71  \w     73.00 111.00   0.50    2.90    --  100.00  69.00   8.16   76
 72  \w    132.00 157.00   0.50    2.90    --  100.00  69.00   8.16   50
 73  \w     76.00 101.00   0.50    2.90    --  100.00  61.00  30.00   50
 74  \w     73.00  98.00   0.50    2.90    --  100.00  69.00  90.00   50
 75  \w     80.00 105.00   0.50    2.90    --  100.00  45.00 120.00   50
 76  \w    116.00 157.00   0.50    2.90    --  100.00  45.00  60.00   82
 77  \w     81.00 106.00   0.50    2.90    --  100.00  45.00  60.00   50
 78  \w    117.00 150.00   0.50    2.90    --  100.00 107.00 -60.00   66
 79  \w     75.00 101.00   0.50    2.90    --  100.00  61.00 120.00   52
 80  \w     75.00 100.00   0.50    2.90    --  100.00  61.00  57.26   50
 81  \w    132.00 157.00   0.50    2.90    --  100.00  91.00 -90.00   50
 82  \w     76.00 155.00   0.50    2.90    --  100.00  56.00  30.68  158
 83  \w     84.00 114.00   0.50    2.90    --  100.00  91.00 -90.00   60
 84  \w     76.00 102.00   0.50    2.90    --  100.00  61.00  90.00   52
 85  \w     73.00 119.00   0.50    2.90    --  100.00  69.00  60.00   92
 86  \w    108.00 133.00   0.50    2.90    --  100.00  45.00 120.00   50
 87  \w     79.00 105.00   0.50    2.90    --  100.00  53.00   0.00   52
 88  \w     73.00  98.00   0.50    2.90    --  100.00  69.00  30.00   50
 89  \w     73.00 104.00   0.50    2.90    --  100.00  69.00   0.00   62
 90  \w     76.00 142.00   0.50    2.90    --  100.00  61.00  60.00  132
 91  \w    118.00 143.00   0.50    2.90    --  100.00  77.00 150.00   50
 92  \w     77.00 102.00   0.50    2.90    --  100.00  53.00  30.00   50
 93  \w     72.00  98.00   0.50    2.90    --  100.00  71.00   0.68   52
 94  \w     74.00  99.00   0.50    2.90    --  100.00  69.00 -30.00   50
 95  \w     68.00  93.00   0.50    2.90    --  100.00  15.00-180.00   50
 96  \w     77.00 131.00   0.50    2.90    --  100.00  53.00  90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033637000
_diffrn_orient_matrix_UB_12      0.0375077000
_diffrn_orient_matrix_UB_13      -0.0957131000
_diffrn_orient_matrix_UB_21      -0.1259075000
_diffrn_orient_matrix_UB_22      0.0431579000
_diffrn_orient_matrix_UB_23      0.0058665000
_diffrn_orient_matrix_UB_31      0.0551665000
_diffrn_orient_matrix_UB_32      0.0961979000
_diffrn_orient_matrix_UB_33      0.0348098000
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12181
_diffrn_reflns_point_group_measured_fraction_full 0.840
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.141
_diffrn_reflns_theta_min         4.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             1152
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.801
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0312
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                3571
_reflns_number_total             3636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           24799_skm158_auto
_cod_database_code               7064194
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C H N O '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00C), C00O(H00D,H00E), C00Q(H00H,H00K), C00R(H00L,H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00M(H00M),
 C00P(H00P), C00S(H00S)
;
_shelx_res_checksum              98175
_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 1.777
_oxdiff_exptl_absorpt_empirical_full_min 0.808