Enantioselective copper-catalysed defluorinative alkylation of polyfluoroarenes with alkenes and 1,3-dienes
Shi, Dazhen; Zhu, Lihan; Jiang, Ying; Wang, Simin; Yin, Jianjun; Yuan, Xiuping; Ma, Shucheng; Li, Xiaoyu; Sun, Jiaqiong; Zhang, Qian; Xiong, Tao; Chemical Science  (2025) –; doi:10.1039/D5SC08090H

data_1576318
_publ_section_title
;
 Enantioselective copper-catalysed defluorinative alkylation of
 polyfluoroarenes with alkenes and 1,3-dienes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08090H
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H12 F5 N O'
_chemical_formula_sum            'C21 H12 F5 N O'
_chemical_formula_weight         389.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-08-20 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7489(9)
_cell_length_b                   15.981(3)
_cell_length_c                   19.362(3)
_cell_measurement_reflns_used    9612
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      63.735
_cell_measurement_theta_min      2.282
_cell_volume                     1778.8(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15788
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        63.815
_diffrn_reflns_theta_max         63.815
_diffrn_reflns_theta_min         3.586
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0783 after correction.
The Ratio of minimum to maximum transmission is 0.7814.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0343P)^2^+0.3202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0815
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2628
_reflns_number_total             2922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08090h2.cif
_cod_data_source_block           xiongt230705_1_0m_pl
_cod_database_code               1576318
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.04(19)
 -0.04(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C02G(H02G)
3.b Aromatic/amide H refined with riding coordinates:
 C01O(H01O), C01Q(H01Q), C01T(H01T), C023(H023), C029(H029), C02C(H02C),
 C02I(H02I), C030(H030)
3.c Idealised Me refined as rotating group:
 C02W(H02A,H02B,H02D)
;
_shelx_res_checksum              65464
_olex2_submission_special_instructions 'No special instructions were received'