Palladium-catalyzed regio- and stereo-selective phosphination of cyclic biarylsulfonium salts to access atropoisomeric phosphines.
Sun, Jinghui; Yan, Yifei; Chen, Xuanxuan; Huang, Zhiwei; Huang, Yinhua; Chemical science 15 (2024) 6943–6948; doi:10.1039/d4sc00446a

data_1571409
_publ_section_title
;
 Palladium-catalyzed regio- and stereo-selective phosphination of cyclic
 biarylsulfonium salts to access atropoisomeric phosphines.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              6943
_journal_page_last               6948
_journal_paper_doi               10.1039/d4sc00446a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H31 P S'
_chemical_formula_sum            'C40 H31 P S'
_chemical_formula_weight         574.68
_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     dual
_audit_creation_date             2023-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.610(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1621(3)
_cell_length_b                   11.2980(4)
_cell_length_c                   16.5498(6)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      2.470
_cell_volume                     1521.21(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48812
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.185
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1069 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         7005
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0441P)^2^+0.4585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6673
_reflns_number_total             7005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00446a2.cif
_cod_data_source_block           mo_231106_sjh_hp1_0m
_cod_depositor_comments
'Adding full bibliography for 1571408--1571410.cif.'
_cod_database_code               1571409
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C27(H27), C15(H15), C30(H30), C35(H35), C20(H20), C36(H36), C16(H16),
 C31(H31), C26(H26), C39(H39), C38(H38), C32(H32), C33(H33), C23(H23), C9(H9),
 C6(H6), C21(H21), C22(H22), C4(H4), C3(H3), C13(H13), C11(H11), C10(H10),
 C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              94625
_olex2_submission_special_instructions 'No special instructions were received'