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_4135364
_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 rmad
_chemical_formula_moiety         'C20 H26 N O2 P'
_chemical_formula_sum            'C20 H26 N O2 P'
_chemical_formula_weight         343.39
_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     dual
_audit_creation_date             2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9196(3)
_cell_length_b                   8.5050(4)
_cell_length_c                   27.3040(12)
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.89
_cell_measurement_theta_min      4.74
_cell_volume                     1839.09(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0608
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11473
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.863
_diffrn_reflns_theta_min         4.738
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1618 before and 0.0832 after correction. The Ratio of minimum to maximum transmission is 0.7202. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1060 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0408P)^2^+1.1508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2938
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09654_si_002.cif
_cod_data_source_block           mj19757_0m
_cod_depositor_comments
'Adding full bibliography for 4135364--4135366.cif.'
_cod_database_code               4135364
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.947
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              92616
_shelx_hkl_checksum              42268
_olex2_submission_special_instructions 'No special instructions were received'