Stereoselective additions to alkenylphosphonium salts for the synthesis of P-stereogenic compounds
Chen, Xiao-Bing; Padín, Damián; Feringa, Ben L.; Chemical Science  (2026) –; doi:10.1039/D5SC09946C

data_1576617
_publ_section_title
;
 Stereoselective additions to alkenylphosphonium salts for the synthesis
 of P-stereogenic compounds.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              7575
_journal_page_last               7581
_journal_paper_doi               10.1039/d5sc09946c
_journal_volume                  17
_journal_year                    2026
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C44 H40 N O4 P'
_chemical_formula_sum            'C44 H40 N O4 P'
_chemical_formula_weight         677.74
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2026-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-27 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7645(3)
_cell_length_b                   12.7645(3)
_cell_length_c                   25.9354(10)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.27
_cell_measurement_theta_min      3.46
_cell_volume                     4225.7(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1166
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            154703
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.462
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1543 before and 0.1199 after correction.
The Ratio of minimum to maximum transmission is 0.8106.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_description       plate
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 3230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.084(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0547
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1001P)^2^+0.7187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1462
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7116
_reflns_number_total             7740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09946c2.cif
_cod_data_source_block           cu_cns_xb_0804_0m_a
_cod_depositor_comments          'Adding full bibliography for 1576617.cif.'
_cod_original_cell_volume        4225.7(3)
_cod_database_code               1576617
_shelx_shelxl_version_number     2025/1
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.698
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C40(H40), C2(H2), C13(H13), C33(H33), C18(H18), C16(H16),
 C8(H8), C17(H17), C29(H29), C34(H34), C25(H25), C44(H44), C38(H38), C3(H3),
 C26(H26), C5(H5), C37(H37), C41(H41), C42(H42), C6(H6), C43(H43), C7(H7),
 C28(H28), C27(H27)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C36(H36A,H36B,H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              12839
_shelx_fab_checksum              23513
_olex2_submission_special_instructions 'No special instructions were received'