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_7064195
_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         'C15 H18 Cl3 N O2'
_chemical_formula_sum            'C15 H18 Cl3 N O2'
_chemical_formula_weight         350.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-03
_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                76.702(2)
_cell_angle_beta                 83.835(2)
_cell_angle_gamma                75.793(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2834(2)
_cell_length_b                   11.5385(4)
_cell_length_c                   16.7356(2)
_cell_measurement_reflns_used    15306
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.4250
_cell_measurement_theta_min      2.7480
_cell_volume                     1688.77(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.997
_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     35.00  97.00   0.50    0.20    --   47.38  40.00-153.00  124
  2  \w    102.00 178.00   0.50    1.00    --  113.25  40.00-153.00  152
  3  \w    103.00 169.00   0.50    1.00    --  113.25  45.00 -90.00  132
  4  \w    115.00 147.00   0.50    1.00    --  113.25  15.00 -30.00   64
  5  \w    151.00 177.00   0.50    1.00    --  113.25  15.00 -30.00   52
  6  \w    100.00 138.00   0.50    1.00    --  113.25  15.00 -90.00   76
  7  \w    102.00 162.00   0.50    1.00    --  113.25  61.00  60.00  120
  8  \w     99.00 152.00   0.50    1.00    --  113.25  61.00 120.00  106
  9  \w     -8.00  25.00   0.50    0.20    --  -47.38  40.00-153.00   66
 10  \w    -71.00 -46.00   0.50    1.00    -- -106.00  61.00-150.00   50
 11  \w   -102.00 -76.00   0.50    1.00    -- -106.00  77.00   0.00   52
 12  \w    -62.00 -11.00   0.50    0.20    --  -47.38  57.00   0.00  102
 13  \w    -24.00  48.00   0.50    0.20    --   47.38 -57.00-180.00  144
 14  \w    -26.00  26.00   0.50    0.20    --   47.38 -19.00-150.00  104
 15  \w    -27.00  25.00   0.50    0.20    --   47.38 -19.00 -90.00  104
 16  \w      7.00  32.00   0.50    0.20    --   47.38 -40.00  52.00   50
 17  \w     46.00  71.00   0.50    1.00    --  113.25 -61.00 -90.00   50
 18  \w     43.00  70.00   0.50    1.00    --  113.25 -61.00 -60.00   54
 19  \w     44.00  69.00   0.50    1.00    --  113.25 -61.00-150.00   50
 20  \w     46.00  71.00   0.50    1.00    --  113.25 -61.00-180.00   50
 21  \w     48.00  88.00   0.50    1.00    --  113.25 -94.00  30.00   80
 22  \w     81.00 107.00   0.50    1.00    --  113.25-104.00 177.79   52
 23  \w     45.00  71.00   0.50    1.00    --  113.25-104.00 177.79   52
 24  \w     51.00  95.00   0.50    1.00    --  113.25 -94.00  90.00   88
 25  \w     44.00  75.00   0.50    1.00    --  113.25-125.00  90.00   62
 26  \w     47.00 104.00   0.50    1.00    --  113.25-125.00  30.00  114
 27  \w     53.00 100.00   0.50    1.00    --  113.25 -94.00-120.00   94
 28  \w     43.00  85.00   0.50    1.00    --  113.25-125.00-150.00   84
 29  \w     63.00 105.00   0.50    1.00    --  113.25 -94.00-180.00   84
 30  \w    -67.00 -34.00   0.50    1.00    -- -106.00 143.00-100.80   66
 31  \w   -124.00 -76.00   0.50    1.00    -- -106.00 143.00-100.80   96
 32  \w    -80.00 -44.00   0.50    1.00    -- -106.00 125.00 -30.00   72
 33  \w    -88.00 -30.00   0.50    0.20    --  -47.38 125.00   0.00  116
 34  \w   -112.00 -68.00   0.50    1.00    -- -106.00 125.00  30.00   88
 35  \w   -112.00 -77.00   0.50    1.00    -- -106.00 125.00  60.00   70
 36  \w    -74.00 -33.00   0.50    1.00    -- -106.00 125.00  60.00   82
 37  \w   -107.00 -36.00   0.50    1.00    -- -106.00 125.00  90.00  142
 38  \w   -112.00 -86.00   0.50    1.00    -- -106.00 125.00 150.00   52
 39  \w    -75.00 -38.00   0.50    1.00    -- -106.00 125.00 150.00   74
 40  \w   -112.00 -82.00   0.50    1.00    -- -106.00 125.00   0.00   60
 41  \w   -109.00 -78.00   0.50    1.00    -- -106.00 115.00 -48.37   62
 42  \w    -65.00 -36.00   0.50    1.00    -- -106.00 110.00-106.89   58
 43  \w   -106.00 -68.00   0.50    1.00    -- -106.00 110.00-106.89   76
 44  \w   -108.00 -77.00   0.50    1.00    -- -106.00 111.00-139.85   62
 45  \w   -119.00 -37.00   0.50    0.20    --  -47.38 -40.00  52.00  164
 46  \w   -174.00-137.00   0.50    1.00    -- -106.00 -94.00 150.00   74
 47  \w   -121.00 -84.00   0.50    1.00    -- -106.00 -94.00 150.00   74
 48  \w   -168.00 -94.00   0.50    1.00    -- -106.00 -40.00  52.00  148
 49  \w   -176.00 -96.00   0.50    1.00    -- -106.00 -45.00  30.00  160
;
_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      0.1346300000
_diffrn_orient_matrix_UB_12      0.0299800000
_diffrn_orient_matrix_UB_13      0.0305242000
_diffrn_orient_matrix_UB_21      -0.0598365000
_diffrn_orient_matrix_UB_22      0.1368047000
_diffrn_orient_matrix_UB_23      -0.0365989000
_diffrn_orient_matrix_UB_31      -0.0876586000
_diffrn_orient_matrix_UB_32      0.0155281000
_diffrn_orient_matrix_UB_33      0.0818660000
_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  0.0480
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21599
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         2.717
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14642
_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    1.379
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0573P)^2^+0.3099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5749
_reflns_number_total             6387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           25750_skm2
_cod_database_code               7064195
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H18 Cl3 N O2'
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.338
_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:
 C12(H12), C12'(H12')
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C3'(H3'), C6'(H6')
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C),
 C7'(H7'A,H7'B,H7'C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,H9'C), C15'(H15D,H15E,
 H15F)
;
_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 5.806
_oxdiff_exptl_absorpt_empirical_full_min 0.576