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_7064189
_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(C24 H42 B21 P), C7 H8'
_chemical_formula_sum            'C55 H92 B42 P2'
_chemical_formula_weight         1269.25
_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   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2pmws0
_audit_creation_date             2025-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-26 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7277(3)
_cell_length_b                   13.6449(4)
_cell_length_c                   21.3554(7)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.28
_cell_volume                     3634.03(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            80540
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.111
_diffrn_reflns_theta_min         2.282
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.8710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.9084.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       SLAB
_exptl_crystal_F_000             1324
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         7997
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0688
_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^)+(0.0861P)^2^+4.8536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.2210
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5610
_reflns_number_total             7997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           PPh3-HBMeoCb2
_cod_database_code               7064189
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Restrained distances
 C1A-C1B
 1.51 with sigma of 0.02
 C1B-C1C = C1B-C1G = C1D-C1E
 1.39 with sigma of 0.02
 C1C-C1D = C1E-C1F = C1F-C1G
 1.38 with sigma of 0.02
 C1A-C1C = C1A-C1G
 2.52 with sigma of 0.04
 C1B-C1D
 2.42 with sigma of 0.04
 C1B-C1F
 2.41 with sigma of 0.04
 C1C-C1E
 2.39 with sigma of 0.04
 C1D-C1F = C1E-C1G
 2.4 with sigma of 0.04
 C1B-C1C \\sim C1C-C1D \\sim C1D-C1E \\sim C1E-C1F \\sim C1F-C1G \\sim C1G-C1B
 with sigma of 0.02
 C1B-C1F \\sim C1B-C1D \\sim C1G-C1E \\sim C1C-C1G \\sim C1D-C1F \\sim C1C-C1E
 with sigma of 0.04
 C1A-C1G \\sim C1A-C1C
 with sigma of 0.04
2. Restrained planarity
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C1A \\sim C1B \\sim C1C \\sim C1D \\sim C1E \\sim C1F \\sim C1G: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C1A, C1B, C1C, C1D, C1E, C1F, C1G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C1A(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5) C1B(0.5) C1C(0.5) H1C(0.5)
 C1D(0.5) H1D(0.5) C1E(0.5) H1E(0.5) C1F(0.5) H1F(0.5) C1G(0.5) H1G(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C12(H12), C8(H8), C24(H24), C21(H21), C9(H9), C11(H11), C23(H23),
 C18(H18), C22(H22), C14(H14), C10(H10), C16(H16), C17(H17), C15(H15), C1C(H1C),
  C1D(H1D), C1E(H1E), C1F(H1F), C1G(H1G)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C1A(H1AA,H1AB,H1AC)
6.c Boron cage BH refined with riding coordinates:
 B4(H4), B12(H12A), B13(H13), B3(H3), B2(H2), B5(H5), B6(H6), B15(H15A),
 B14(H14A), B17(H17A), B10(H10A), B18(H18A), B16(H16A), B9(H9A), B19(H19),
 B21(H21A), B7(H7), B11(H11A), B20(H20A), B8(H8A)
;
_shelx_res_checksum              15466
_olex2_submission_special_instructions 'No special instructions were received'