Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides.
Li, Yan-Bo; Tian, Hu; Yin, Liang; Journal of the American Chemical Society 142 (2020) 20098–20106; doi:10.1021/jacs.0c09654

data_4135366
_publ_section_title
;
 Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of
 \a,\b-Unsaturated Amides.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20098
_journal_page_last               20106
_journal_paper_doi               10.1021/jacs.0c09654
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H41 Cl N2 O4 P2 Pd'
_chemical_formula_sum            'C40 H41 Cl N2 O4 P2 Pd'
_chemical_formula_weight         817.54
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-12
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 92.9610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6291(3)
_cell_length_b                   31.7456(8)
_cell_length_c                   11.4376(3)
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    193
_cell_measurement_theta_max      54.848
_cell_measurement_theta_min      5.133
_cell_volume                     3854.20(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            55217
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         1.895
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
; 
 Flack x determined using 7608 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.017(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     909
_refine_ls_number_reflns         17640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.808
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                16600
_reflns_number_total             17640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09654_si_004.cif
_cod_data_source_block           mo_d8v20429_0m
_cod_depositor_comments
'Adding full bibliography for 4135364--4135366.cif.'
_cod_database_code               4135366
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.894
_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 
2.a Ternary CH refined with riding coordinates: 
 C7(H7), C12(H12), C47(H47), C52(H52) 
2.b Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C13(H13A,H13B), C48(H48A,H48B), C53(H53A,H53B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), 
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), 
  C33(H33), C34(H34), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), 
 C43(H43), C44(H44), C45(H45), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), 
  C64(H64), C65(H65), C66(H66), C67(H67), C68(H68), C70(H70), C71(H71), 
 C72(H72), C73(H73), C74(H74), C76(H76), C77(H77), C78(H78), C79(H79), C80(H80) 
2.d Idealised Me refined as rotating group: 
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B, 
 H16C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C55(H55A,H55B,H55C), C56(H56A, 
 H56B,H56C) 
;
_shelx_res_checksum              10936
_shelx_hkl_checksum              50018
_shelx_fab_checksum              72293
_olex2_submission_special_instructions 'No special instructions were received'