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_7064196
_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         '3(C16 H12 Br Cl3 O2)'
_chemical_formula_sum            'C48 H36 Br3 Cl9 O6'
_chemical_formula_weight         1267.55
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_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                120
_cell_formula_units_Z            6
_cell_length_a                   39.1114(7)
_cell_length_b                   39.1114(7)
_cell_length_c                   5.87550(10)
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.3710
_cell_measurement_theta_min      2.3860
_cell_volume                     7783.6(2)
_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, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_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   -116.00 -53.00   0.50   10.00    --  -47.51-155.00-119.00  126
  2  \w     46.00 107.00   0.50   40.00    --  113.25-119.00  36.00  122
  3  \w     43.00  76.00   0.50   40.00    --  113.25 -74.00 -79.00   66
  4  \w    108.00 134.00   0.50   40.00    --  113.25  74.00  48.00   52
  5  \w     74.00 101.00   0.50   10.00    --   47.51 125.00   0.00   54
  6  \w     -3.00  22.00   0.50   10.00    --   47.51 -19.00-180.00   50
  7  \w    -67.00 -42.00   0.50   40.00    -- -106.00  61.00  30.00   50
  8  \w   -172.00-147.00   0.50   40.00    -- -106.00 -30.00 -60.00   50
  9  \w   -121.00 -95.00   0.50   40.00    -- -106.00 -30.00 -60.00   52
 10  \w     44.00  69.00   0.50   40.00    --  113.25 -61.00 150.00   50
 11  \w    116.00 175.00   0.50   40.00    --  113.25  15.00  30.00  118
 12  \w     79.00 106.00   0.50   40.00    --  113.25 -77.00 -90.00   54
 13  \w     45.00  71.00   0.50   40.00    --  113.25 -77.00 -90.00   52
 14  \w     42.00  67.00   0.50   40.00    --  113.25 -61.00-180.00   50
 15  \w     54.00 105.00   0.50   40.00    --  113.25 -94.00-150.00  102
;
_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      0.0250858000
_diffrn_orient_matrix_UB_12      -0.0193729000
_diffrn_orient_matrix_UB_13      0.0514631000
_diffrn_orient_matrix_UB_21      -0.0095940000
_diffrn_orient_matrix_UB_22      -0.0011902000
_diffrn_orient_matrix_UB_23      0.2552548000
_diffrn_orient_matrix_UB_31      -0.0366906000
_diffrn_orient_matrix_UB_32      -0.0411422000
_diffrn_orient_matrix_UB_33      -0.0317165000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8516
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_min         4.522
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70083
_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    1.622
_exptl_crystal_description       prism
_exptl_crystal_F_000             3780
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         3.355
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0867P)^2^+44.4227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             3205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           098-010_bna
_cod_original_cell_volume        7783.6(3)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7064196
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H10 N2 O2'
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.621
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00C,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_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 3.049
_oxdiff_exptl_absorpt_empirical_full_min 0.303