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_1575050
_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_absolute_configuration rmad
_chemical_formula_moiety         'C30 H33 N O5 S'
_chemical_formula_sum            'C30 H33 N O5 S'
_chemical_formula_weight         519.666
_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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2m3tzk
_audit_creation_date             2024-05-25
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0206(9)
_cell_length_b                   15.6245(14)
_cell_length_c                   17.2804(16)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    183.00
_cell_measurement_theta_max      68.251
_cell_measurement_theta_min      5.663
_cell_volume                     2705.5(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      183.00
_diffrn_measured_fraction_theta_full 0.9892
_diffrn_measured_fraction_theta_max 0.9893
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.9892
_diffrn_reflns_Laue_measured_fraction_max 0.9893
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19126
_diffrn_reflns_point_group_measured_fraction_full 0.9791
_diffrn_reflns_point_group_measured_fraction_max 0.9786
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_min         5.12
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.387
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             1108.861
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2748
_refine_diff_density_min         -0.1945
_refine_diff_density_rms         0.0345
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.038(6)
_refine_ls_d_res_high            0.8299
_refine_ls_d_res_low             8.6402
_refine_ls_goodness_of_fit_ref   1.0479
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0479
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.965
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                4733
_reflns_number_total             4848
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5sc04080a2.cif
_cod_data_source_block           B
_cod_depositor_comments
'Adding full bibliography for 1575048--1575050.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1575050
_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:
 C00Z(H00Z)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00b,H00c), C00Y(H00y,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00W(H00W), C00R(H00R), C00J(H00J), C00Q(H00Q), C00D(H00D),
 C00S(H00S), C00T(H00T), C00A(H00A), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C00H(H00e,H00f,H00g), C00O(H00h,H00i,H00k), C00U(H00l,H00n,H00o), C00V(H00p,
 H00u,H00v), C010(H01a,H01b,H01c), C011(H01d,H01e,H01f)
;
_olex2_submission_special_instructions 'No special instructions were received'