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_7064190
_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_absolute_configuration unk
_chemical_formula_moiety         'C11 H8 Cl3 F3 O'
_chemical_formula_sum            'C11 H8 Cl3 F3 O'
_chemical_formula_weight         319.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-09-26 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.76450(10)
_cell_length_b                   12.1514(2)
_cell_length_c                   18.0507(2)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.0550
_cell_measurement_theta_min      4.3730
_cell_volume                     1264.39(3)
_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 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            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -21.00  30.00   0.50    0.20    --  -35.49  59.00-113.00  102
  2  \w    -37.00  25.00   0.50    0.20    --  -35.49  80.00 110.00  124
  3  \w    -42.00 -17.00   0.50    0.20    --  -35.49  84.00   0.00   50
  4  \w     15.00  59.00   0.50    0.20    --   35.49 -59.00 106.00   88
  5  \w    -26.00   3.00   0.50    0.20    --   35.49 -59.00 106.00   58
  6  \w     36.00  63.00   0.50    0.20    --   35.49 -84.00-119.00   54
  7  \w    -16.00  22.00   0.50    0.20    --   35.49 -80.00 -12.00   76
  8  \w    107.00 140.00   0.50    0.80    --  100.00  59.00-113.00   66
  9  \w     55.00  80.00   0.50    0.80    --  100.00 -80.00 -12.00   50
 10  \w     96.00 121.00   0.50    0.80    --  100.00 -59.00 106.00   50
 11  \w     90.00 130.00   0.50    0.80    --  100.00  80.00 110.00   80
 12  \w     95.00 121.00   0.50    0.80    --  100.00 -84.00-119.00   52
 13  \w     36.00  69.00   0.50    0.80    --  100.00 -84.00-119.00   66
 14  \w    -81.00 -56.00   0.50    0.20    --  -35.49 -59.00 106.00   50
 15  \w     33.00  58.00   0.50    0.20    --   35.49  59.00-113.00   50
 16  \w     15.00  40.00   0.50    0.20    --   35.49-138.00-120.00   50
 17  \w    -11.00  51.00   0.50    0.20    --   35.49-104.00 -30.00  124
 18  \w     14.00  40.00   0.50    0.20    --   35.49 -43.00 -90.00   52
 19  \w    118.00 146.00   0.50    0.80    --  100.00 107.00-120.00   56
 20  \w    117.00 150.00   0.50    0.80    --  100.00 107.00 -30.00   66
 21  \w    108.00 157.00   0.50    0.80    --  100.00  77.00 -30.00   98
 22  \w     86.00 111.00   0.50    0.80    --  100.00  30.00 -90.00   50
 23  \w     83.00 109.00   0.50    0.80    --  100.00 107.00 -30.00   52
 24  \w    120.00 156.00   0.50    0.80    --  100.00  30.00 -90.00   72
 25  \w     30.00 105.00   0.50    0.80    --  100.00 -37.00 -90.00  150
 26  \w     93.00 157.00   0.50    0.80    --  100.00  77.00-180.00  128
 27  \w     92.00 117.00   0.50    0.80    --  100.00 107.00-180.00   50
 28  \w    100.00 153.00   0.50    0.80    --  100.00  77.00 -90.00  106
 29  \w     99.00 157.00   0.50    0.80    --  100.00  91.00 -60.00  116
 30  \w     79.00 104.00   0.50    0.80    --  100.00 -80.00 -12.00   50
 31  \w    -81.00 -34.00   0.50    0.20    --  -35.49 -43.00  30.00   94
 32  \w     63.00  88.00   0.50    0.20    --   35.49-138.00-180.00   50
 33  \w     76.00 102.00   0.50    0.80    --  100.00-107.00 120.00   52
 34  \w     79.00 116.00   0.50    0.80    --  100.00  53.00-150.00   74
 35  \w     38.00  64.00   0.50    0.80    --  100.00-107.00   0.00   52
 36  \w     75.00 107.00   0.50    0.80    --  100.00-107.00   0.00   64
 37  \w     82.00 111.00   0.50    0.80    --  100.00-125.00 120.00   58
 38  \w     31.00  56.00   0.50    0.80    --  100.00-125.00 120.00   50
 39  \w     91.00 120.00   0.50    0.80    --  100.00  37.00  60.00   58
 40  \w     94.00 130.00   0.50    0.80    --  100.00  53.00 -90.00   72
 41  \w     28.00  59.00   0.50    0.80    --  100.00-107.00 120.00   62
 42  \w     32.00  58.00   0.50    0.80    --  100.00-125.00-120.00   52
 43  \w     83.00 110.00   0.50    0.80    --  100.00-125.00-120.00   54
 44  \w     30.00  56.00   0.50    0.80    --  100.00 -30.00  60.00   52
 45  \w     90.00 116.00   0.50    0.80    --  100.00 -30.00  60.00   52
 46  \w    105.00 130.00   0.50    0.80    --  100.00  91.00-180.00   50
 47  \w    119.00 153.00   0.50    0.80    --  100.00  77.00 150.00   68
;
_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      0.1869213000
_diffrn_orient_matrix_UB_12      -0.0713865000
_diffrn_orient_matrix_UB_13      0.0375775000
_diffrn_orient_matrix_UB_21      -0.0111555000
_diffrn_orient_matrix_UB_22      -0.0820158000
_diffrn_orient_matrix_UB_23      -0.0649725000
_diffrn_orient_matrix_UB_31      0.1907428000
_diffrn_orient_matrix_UB_32      0.0651854000
_diffrn_orient_matrix_UB_33      -0.0406052000
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.075
_diffrn_reflns_theta_min         4.386
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63871
_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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0292
_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^)+(0.0356P)^2^+0.8616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2312
_reflns_number_total             2348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           25718_skm220
_cod_database_code               7064190
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H8 Cl3 F3 O'
_shelx_estimated_absorpt_t_max   0.647
_shelx_estimated_absorpt_t_min   0.409
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F2) = Uanis(F2')
Uanis(F1') = Uanis(F1)
Uanis(F3) = Uanis(F3')
3. Others
 Sof(F1')=Sof(F2')=Sof(F3')=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
;
_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 1.881
_oxdiff_exptl_absorpt_empirical_full_min 0.636