Palladium-catalyzed redox diversified entry to axially chiral styrenes <i>via</i> asymmetric olefination with alkynes.
Lin, Ziwei; Jiang, Yuqing; Wang, Fen; Huang, Genping; Li, Jessica; Li, Xingwei; Chemical science 16 (2025) 14252–14261; doi:10.1039/d5sc04080a

data_1575048
_publ_section_title
;
 Palladium-catalyzed redox diversified entry to axially chiral styrenes
 <i>via</i> asymmetric olefination with alkynes.
;
_journal_issue                   31
_journal_name_full               'Chemical science'
_journal_page_first              14252
_journal_page_last               14261
_journal_paper_doi               10.1039/d5sc04080a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C24 H19 F O3'
_chemical_formula_sum            'C24 H19 F O3'
_chemical_formula_weight         374.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2m3tyj
_audit_creation_date             2024-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-14 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2269(2)
_cell_length_b                   13.0774(3)
_cell_length_c                   15.7550(4)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      2.85
_cell_volume                     1870.88(8)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27942
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.357
_diffrn_reflns_theta_min         2.850
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0715 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.8741.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 3079 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6718
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0635P)^2^+0.2337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                6626
_reflns_number_total             6718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc04080a2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
'Adding full bibliography for 1575048--1575050.cif.'
_cod_database_code               1575048
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.832
_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 Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C36(H36A,H36B), C44(H44A,H44B), C21(H21A,H21B), C39(H39A,
 H39B), C46(H46A,H46B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C17(H17), C28(H28), C29(H29), C37(H37), C41(H41),
 C45(H45), C47(H47), C48(H48), C2(H2), C5(H5), C9(H9), C24(H24), C26(H26),
 C30(H30), C33(H33), C34(H34), C35(H35), C38(H38)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C43(H43A,H43B,H43C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              97759
_shelx_fab_checksum              24381
_olex2_submission_special_instructions 'No special instructions were received'