Copper(I)-catalyzed asymmetric addition of diarylphosphine sulfides to aldimines.
Xie, Dong-Liang; Tian, Hu; Yin, Liang; Organic & biomolecular chemistry 23 (2025) 6106–6110; doi:10.1039/d5ob00682a

data_7160567
_publ_section_title
;
 Copper(I)-catalyzed asymmetric addition of diarylphosphine sulfides to
 aldimines.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6106
_journal_page_last               6110
_journal_paper_doi               10.1039/d5ob00682a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H26 N2 O2 P2 S2'
_chemical_formula_sum            'C31 H26 N2 O2 P2 S2'
_chemical_formula_weight         584.60
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-28 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.3800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1496(3)
_cell_length_b                   14.1579(4)
_cell_length_c                   15.3629(4)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.890
_cell_measurement_theta_min      3.695
_cell_volume                     2860.06(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37784
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.865
_diffrn_reflns_theta_min         2.502
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1215 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.8055.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 3613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.073(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         10134
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+3.5097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                9207
_reflns_number_total             10134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00682a2.cif
_cod_data_source_block           mj25029_0m
_cod_depositor_comments          'Adding full bibliography for 7160567.cif.'
_cod_database_code               7160567
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.730
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C1A, C2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Riding coordinates:
 N1(H1)
3.b Ternary CH refined with riding coordinates:
 C1(H1A), C1A(H1AB)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30),
 C31(H31), N1A(H1AA), C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A), C23A(H23A),
 C24A(H24A), C25A(H25A), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A),
 C31A(H31A)
;
_shelx_res_checksum              70350
_olex2_submission_special_instructions 'No special instructions were received'