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_1571410
_publ_section_title
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 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         'C39 H29 P S'
_chemical_formula_sum            'C39 H29 P S'
_chemical_formula_weight         560.65
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_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                112.211(2)
_cell_angle_beta                 104.135(2)
_cell_angle_gamma                103.663(2)
_cell_formula_units_Z            3
_cell_length_a                   11.0390(6)
_cell_length_b                   15.1879(8)
_cell_length_c                   16.0708(7)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.424
_cell_measurement_theta_min      2.517
_cell_volume                     2251.2(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0626
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            109565
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.044
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0745 after correction.
The Ratio of minimum to maximum transmission is 0.9536.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             882
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 7546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1111
_refine_ls_number_reflns         20597
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0420P)^2^+0.7923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                18057
_reflns_number_total             20597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00446a2.cif
_cod_data_source_block           mo_230915_hyh_p1_0m
_cod_depositor_comments
'Adding full bibliography for 1571408--1571410.cif.'
_cod_database_code               1571410
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.967
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C43(H43), C44(H44), C48(H48),
  C49(H49), C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60),
 C63(H63), C64(H64), C65(H65), C66(H66), C68(H68), C69(H69), C70(H70), C71(H71),
  C72(H72), C74(H74), C75(H75), C76(H76), C77(H77), C78(H78), C79(H79),
 C80(H80), C82(H82), C83(H83), C87(H87), C88(H88), C92(H92), C93(H93), C94(H94),
  C95(H95), C98(H98), C99(H99), C102(H102), C103(H103), C104(H104), C105(H105),
 C107(H107), C108(H108), C109(H109), C110(H110), C111(H111), C113(H113),
 C114(H114), C115(H115), C116(H116), C117(H117)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C46(H46A,H46B,H46C), C85(H85A,H85B,H85C)
;
_shelx_res_checksum              11753
_olex2_submission_special_instructions 'No special instructions were received'