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_7064193
_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 Cl3 N O2'
_chemical_formula_sum            'C12 H11 Cl3 N O2'
_chemical_formula_weight         307.57
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-11
_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                 109.786(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7611(4)
_cell_length_b                   14.0190(4)
_cell_length_c                   9.5719(3)
_cell_measurement_reflns_used    6919
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.6160
_cell_measurement_theta_min      4.3630
_cell_volume                     1358.77(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 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_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    -48.00  14.00   0.50    0.40    --  -47.38  92.00 -67.00  124
  2  \w     26.00  77.00   0.50    0.40    --   47.38 -92.00 179.00  102
  3  \w    -22.00  23.00   0.50    0.40    --   47.38 -92.00 179.00   90
  4  \w    -99.00 -72.00   0.50    1.61    -- -106.00  92.00 -67.00   54
  5  \w     44.00 105.00   0.50    1.61    --  113.25 -92.00 179.00  122
  6  \w    130.00 156.00   0.50    1.61    --  113.25  92.00 -67.00   52
  7  \w    -21.00  26.00   0.50    0.40    --   47.38 -19.00  30.00   94
  8  \w     75.00 120.00   0.50    0.40    --   47.38 125.00-150.00   90
  9  \w     85.00 110.00   0.50    0.40    --   47.38 125.00 120.00   50
 10  \w    -24.00  17.00   0.50    0.40    --   47.38 -19.00  90.00   82
 11  \w    -64.00 -38.00   0.50    1.61    -- -106.00  61.00 -60.00   52
 12  \w    -66.00 -40.00   0.50    1.61    -- -106.00  61.00  90.00   52
 13  \w   -103.00 -56.00   0.50    1.61    -- -106.00  77.00 150.00   94
 14  \w   -169.00 -85.00   0.50    1.61    -- -106.00 -92.00 179.00  168
 15  \w    -71.00 -37.00   0.50    1.61    -- -106.00  61.00 -90.00   68
 16  \w    -64.00 -39.00   0.50    1.61    -- -106.00  61.00 150.00   50
 17  \w    -67.00 -41.00   0.50    1.61    -- -106.00  61.00 120.00   52
 18  \w     44.00  69.00   0.50    1.61    --  113.25 -61.00  30.00   50
 19  \w     42.00  67.00   0.50    1.61    --  113.25 -61.00   0.00   50
 20  \w     54.00  92.00   0.50    1.61    --  113.25 -77.00-180.00   76
 21  \w     45.00  70.00   0.50    1.61    --  113.25 -61.00-150.00   50
 22  \w     42.00  67.00   0.50    1.61    --  113.25 -61.00 -30.00   50
 23  \w     47.00 111.00   0.50    1.61    --  113.25-125.00 -30.00  128
 24  \w     98.00 177.00   0.50    1.61    --  113.25  61.00 -30.00  158
 25  \w    104.00 170.00   0.50    1.61    --  113.25  30.00-120.00  132
 26  \w     42.00  69.00   0.50    1.61    --  113.25 -77.00   0.00   54
 27  \w     43.00  68.00   0.50    1.61    --  113.25 -61.00-120.00   50
 28  \w     64.00  89.00   0.50    1.61    --  113.25 -77.00  90.00   50
 29  \w     45.00  70.00   0.50    1.61    --  113.25 -61.00  60.00   50
 30  \w     49.00  74.00   0.50    1.61    --  113.25 -92.00 179.00   50
 31  \w      0.00  26.00   0.50    0.40    --  -47.38  37.00-150.00   52
 32  \w    -26.00  28.00   0.50    0.40    --  -47.38  19.00 -60.00  108
 33  \w    -30.00  -4.00   0.50    0.40    --  -47.38  37.00-150.00   52
 34  \w    -60.00 -24.00   0.50    0.40    --  -47.38  57.00 -90.00   72
 35  \w    -13.00  16.00   0.50    0.40    --   47.38 -19.00 120.00   58
 36  \w     88.00 119.00   0.50    0.40    --   47.38 125.00  60.00   62
 37  \w   -165.00-140.00   0.50    1.61    -- -106.00 -61.00  90.00   50
 38  \w   -114.00 -89.00   0.50    1.61    -- -106.00 -61.00-120.00   50
 39  \w   -112.00 -86.00   0.50    1.61    -- -106.00 125.00 150.00   52
 40  \w   -173.00-147.00   0.50    1.61    -- -106.00 -61.00-120.00   52
 41  \w   -175.00-100.00   0.50    1.61    -- -106.00 -30.00  90.00  150
;
_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      0.1271544000
_diffrn_orient_matrix_UB_12      0.0570155000
_diffrn_orient_matrix_UB_13      0.0772464000
_diffrn_orient_matrix_UB_21      -0.0544011000
_diffrn_orient_matrix_UB_22      0.0837799000
_diffrn_orient_matrix_UB_23      -0.1075432000
_diffrn_orient_matrix_UB_31      -0.0634134000
_diffrn_orient_matrix_UB_32      0.0425468000
_diffrn_orient_matrix_UB_33      0.1082261000
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12878
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.086
_diffrn_reflns_theta_min         4.366
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.061
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87529
_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_density_diffrn    1.504
_exptl_crystal_F_000             628
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0565P)^2^+1.0114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             2855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           25499_skm203_1_auto
_cod_database_code               7064193
_shelxl_version_number           2014/6
_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:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00G), C00G(H00H), C00H(H00I), C00I(H00J)
2.d Idealised Me refined as rotating group:
 C00D(H00D,H00E,H00F)
;
_shelx_res_checksum              33026
_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 1.730
_oxdiff_exptl_absorpt_empirical_full_min 0.665