Catalytic asymmetric construction of remote P or other heteroatom (Si/S) stereogenic axially chiral scaffolds.
Liu, Wenqi; Ling, Zhijie; Liu, Yang-Zi; Deng, Wei-Ping; Chemical science 17 (2026) 240–246; doi:10.1039/d5sc08143b

data_1576192
_publ_section_title
;
 Catalytic asymmetric construction of remote P or other heteroatom (Si/S)
 stereogenic axially chiral scaffolds.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              240
_journal_page_last               246
_journal_paper_doi               10.1039/d5sc08143b
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         '2(C25 H17 N2 O4 P)'
_chemical_formula_sum            'C50 H34 N4 O8 P2'
_chemical_formula_weight         880.75
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-06 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0473(6)
_cell_length_b                   15.0466(6)
_cell_length_c                   19.4211(8)
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    190.00
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.55
_cell_volume                     4104.9(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      190.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.1637
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32001
_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         68.411
_diffrn_reflns_theta_min         3.716
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_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    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2192 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0503P)^2^+2.1850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6206
_reflns_number_total             7514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08143b2.cif
_cod_data_source_block           20250306_l_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 1576192--1576193.cif.'
_cod_database_code               1576192
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.753
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43), C46(H46), C47(H47),
  C48(H48), C49(H49), C50(H50)
;
_shelx_res_checksum              15029
_olex2_submission_special_instructions 'No special instructions were received'