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_7064199
_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         'C11 H27 B21 F4 N, C18 H33 F P'
_chemical_formula_sum            'C29 H60 B21 F5 N P'
_chemical_formula_weight         775.76
_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   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2pmwx4
_audit_creation_date             2025-05-12
_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                76.631(2)
_cell_angle_beta                 82.103(2)
_cell_angle_gamma                88.428(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3795(8)
_cell_length_b                   11.6288(9)
_cell_length_c                   18.0566(12)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.07
_cell_measurement_theta_min      2.34
_cell_volume                     2100.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            80854
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_min         2.362
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.8849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0886 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9229.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       SLAB
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         9266
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0968P)^2^+1.7726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6821
_reflns_number_total             9266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03928b2.cif
_cod_data_source_block           1PCy3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'DIRECT METHOD' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7064199
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C4-C5 \\sim C4-C5A
 with sigma of 0.04
 C4-B12 \\sim C4-B12A
 with sigma of 0.04
 C4-B15 \\sim C4-B15A
 with sigma of 0.04
 C4-B14 \\sim C4-B14A
 with sigma of 0.04
 C4-B13 \\sim C4-B13A
 with sigma of 0.04
 C4-B17 \\sim C4-B17A
 with sigma of 0.04
 C4-B18 \\sim C4-B18A
 with sigma of 0.04
 C4-B16 \\sim C4-B16A
 with sigma of 0.04
 C4-B19 \\sim C4-B19A
 with sigma of 0.04
 C4-B20 \\sim C4-B20A
 with sigma of 0.04
 C4-C6 \\sim C4-C6A
 with sigma of 0.04
 C5-B12 \\sim C5A-B12A
 with sigma of 0.04
 C5-B15 \\sim C5A-B15A
 with sigma of 0.04
 C5-B14 \\sim C5A-B14A
 with sigma of 0.04
 C5-B13 \\sim C5A-B13A
 with sigma of 0.04
 C5-B17 \\sim C5A-B17A
 with sigma of 0.04
 C5-B18 \\sim C5A-B18A
 with sigma of 0.04
 C5-B16 \\sim C5A-B16A
 with sigma of 0.04
 C5-B19 \\sim C5A-B19A
 with sigma of 0.04
 C5-B21 \\sim C5A-B21A
 with sigma of 0.04
 B12-B15 \\sim B12A-B15A
 with sigma of 0.04
 B12-B14 \\sim B12A-B14A
 with sigma of 0.04
 B12-B13 \\sim B12A-B13A
 with sigma of 0.04
 B12-B17 \\sim B12A-B17A
 with sigma of 0.04
 B12-B18 \\sim B12A-B18A
 with sigma of 0.04
 B12-B16 \\sim B12A-B16A
 with sigma of 0.04
 B12-B20 \\sim B12A-B20A
 with sigma of 0.04
 B12-B21 \\sim B12A-B21A
 with sigma of 0.04
 B12-C6 \\sim B12A-C6A
 with sigma of 0.04
 B15-B14 \\sim B15A-B14A
 with sigma of 0.04
 B15-B13 \\sim B15A-B13A
 with sigma of 0.04
 B15-B17 \\sim B15A-B17A
 with sigma of 0.04
 B15-B16 \\sim B15A-B16A
 with sigma of 0.04
 B15-B19 \\sim B15A-B19A
 with sigma of 0.04
 B15-B20 \\sim B15A-B20A
 with sigma of 0.04
 B15-B21 \\sim B15A-B21A
 with sigma of 0.04
 B14-B13 \\sim B14A-B13A
 with sigma of 0.04
 B14-B18 \\sim B14A-B18A
 with sigma of 0.04
 B14-B16 \\sim B14A-B16A
 with sigma of 0.04
 B14-B19 \\sim B14A-B19A
 with sigma of 0.04
 B14-B20 \\sim B14A-B20A
 with sigma of 0.04
 B14-B21 \\sim B14A-B21A
 with sigma of 0.04
 B13-B17 \\sim B13A-B17A
 with sigma of 0.04
 B13-B18 \\sim B13A-B18A
 with sigma of 0.04
 B13-B19 \\sim B13A-B19A
 with sigma of 0.04
 B13-B20 \\sim B13A-B20A
 with sigma of 0.04
 B13-B21 \\sim B13A-B21A
 with sigma of 0.04
 B13-C6 \\sim B13A-C6A
 with sigma of 0.04
 B17-B18 \\sim B17A-B18A
 with sigma of 0.04
 B17-B16 \\sim B17A-B16A
 with sigma of 0.04
 B17-B19 \\sim B17A-B19A
 with sigma of 0.04
 B17-B20 \\sim B17A-B20A
 with sigma of 0.04
 B17-B21 \\sim B17A-B21A
 with sigma of 0.04
 B17-C6 \\sim B17A-C6A
 with sigma of 0.04
 B18-B16 \\sim B18A-B16A
 with sigma of 0.04
 B18-B19 \\sim B18A-B19A
 with sigma of 0.04
 B18-B20 \\sim B18A-B20A
 with sigma of 0.04
 B18-B21 \\sim B18A-B21A
 with sigma of 0.04
 B18-C6 \\sim B18A-C6A
 with sigma of 0.04
 B16-B19 \\sim B16A-B19A
 with sigma of 0.04
 B16-B20 \\sim B16A-B20A
 with sigma of 0.04
 B16-B21 \\sim B16A-B21A
 with sigma of 0.04
 B19-B20 \\sim B19A-B20A
 with sigma of 0.04
 B19-B21 \\sim B19A-B21A
 with sigma of 0.04
 B20-B21 \\sim B20A-B21A
 with sigma of 0.04
3. Others
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C5A)=Sof(B12A)=Sof(H12A)=Sof(B17A)=
 Sof(H17A)=Sof(B18A)=Sof(H18A)=Sof(B13A)=Sof(H13A)=Sof(B15A)=Sof(H15A)=
 Sof(B14A)=Sof(H14A)=Sof(B19A)=Sof(H19A)=Sof(B21A)=Sof(H21A)=Sof(B16A)=
 Sof(H16A)=Sof(B20A)=Sof(H20A)=1-FVAR(1)
 Sof(C5)=Sof(B12)=Sof(H12)=Sof(B15)=Sof(H15)=Sof(B14)=Sof(H14)=Sof(B13)=
 Sof(H13)=Sof(B17)=Sof(H17)=Sof(B18)=Sof(H18)=Sof(B16)=Sof(H16)=Sof(B19)=
 Sof(H19)=Sof(B20)=Sof(H20)=Sof(B21)=Sof(H21)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C24(H24), C12(H12B), C18(H18B), B1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C20(H20B,H20C), C17(H17B,H17C), C19(H19B,H19C), C25(H25A,
 H25B), C23(H23A,H23B), C16(H16B,H16C), C21(H21B,H21C), C13(H13B,H13C),
 C22(H22A,H22B), C26(H26A,H26B), C15(H15B,H15C), C14(H14B,H14C), C28(H28A,H28B),
  C27(H27A,H27B)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
4.d Boron cage BH refined with riding coordinates:
 B12(H12), B3(H3), B5(H5), B4(H4), B15(H15), B7(H7), B10(H10), B9(H9),
 B14(H14), B8(H8), B6(H6), B13(H13), B17(H17), B2(H2), B11(H11), B18(H18),
 B16(H16), B19(H19), B20(H20), B21(H21), B12A(H12A), B17A(H17A), B18A(H18A),
 B13A(H13A), B15A(H15A), B14A(H14A), B19A(H19A), B21A(H21A), B16A(H16A),
 B20A(H20A)
;
_shelx_res_checksum              56889
_olex2_submission_special_instructions 'No special instructions were received'