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_1571408
_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_formula_moiety         '2(C27 H19 S), 2(C F3 O3 S), C3 H6 O'
_chemical_formula_sum            'C59 H44 F6 O7 S4'
_chemical_formula_weight         1107.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-10-24 deposited with the CCDC.	2024-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.6038(16)
_cell_length_b                   12.3774(9)
_cell_length_c                   17.1095(11)
_cell_measurement_reflns_used    7766
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      56.816
_cell_measurement_theta_min      3.258
_cell_volume                     4998.6(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1416
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            71816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.227
_diffrn_reflns_theta_min         3.258
_diffrn_source_current           3.57
_diffrn_source_power             0.24972149999999999
_diffrn_source_voltage           69.95
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1876 before and 0.1198 after correction.
The Ratio of minimum to maximum transmission is 0.7019.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     241
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0737P)^2^+6.7041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1835
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3516
_reflns_number_total             5159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00446a2.cif
_cod_data_source_block           230914_hyh_s1
_cod_depositor_comments
'Adding full bibliography for 1571408--1571410.cif.'
_cod_database_code               1571408
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.797
_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. Restrained distances
 S2-O2 \\sim S2A-O2A
 with sigma of 0.02
 S2-O1 \\sim S2A-O1A
 with sigma of 0.02
 S2-O3 \\sim S2A-O3A
 with sigma of 0.02
 S2-C28 \\sim S2A-C28A
 with sigma of 0.02
 O3-C28 \\sim O3A-C28A
 with sigma of 0.04
 O1-C28 \\sim O1A-C28A
 with sigma of 0.04
 F3-F1 \\sim F3A-F1A
 with sigma of 0.04
 F3-C28 \\sim F3A-C28A
 with sigma of 0.02
 F2-C28 \\sim F2A-C28A
 with sigma of 0.02
 F1-C28 \\sim F1A-C28A
 with sigma of 0.02
 O1-O3 \\sim O1A-O3A
 with sigma of 0.04
 F3-F2 \\sim F3A-F2A
 with sigma of 0.04
 S2-F3 \\sim S2A-F3A
 with sigma of 0.04
 S2-F2 \\sim S2A-F2A
 with sigma of 0.04
 F2-F1 \\sim F2A-F1A
 with sigma of 0.04
 S2-F1 \\sim S2A-F1A
 with sigma of 0.04
 O2-O1 \\sim O2A-O1A
 with sigma of 0.04
 O2-O3 \\sim O2A-O3A
 with sigma of 0.04
 O2-C28 \\sim O2A-C28A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
F1 \\sim O1 \\sim S2 \\sim F2 \\sim O2 \\sim F3 \\sim O3 \\sim C28 \\sim F1A
\\sim O1A \\sim S2A \\sim F2A \\sim O2A \\sim F3A \\sim O3A \\sim C28A: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Others
 Sof(F1A)=Sof(O1A)=Sof(S2A)=Sof(F2A)=Sof(O2A)=Sof(F3A)=Sof(O3A)=Sof(C28A)=1-
 FVAR(1)
 Sof(F1)=Sof(O1)=Sof(S2)=Sof(F2)=Sof(O2)=Sof(F3)=Sof(O3)=Sof(C28)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
5.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              85605
_olex2_submission_special_instructions 'No special instructions were received'