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_4135365
_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         'C21 H28 N O2 P'
_chemical_formula_sum            'C21 H28 N O2 P'
_chemical_formula_weight         357.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0085(3)
_cell_length_b                   7.8446(2)
_cell_length_c                   16.2448(4)
_cell_measurement_reflns_used    9658
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.84
_cell_measurement_theta_min      5.25
_cell_volume                     2036.81(8)
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12501
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.914
_diffrn_reflns_theta_min         5.247
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1346 before and 0.0717 after correction. The Ratio of minimum to maximum transmission is 0.7176. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.7115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3630
_reflns_number_total             3817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09654_si_003.cif
_cod_data_source_block           mj19807_0m
_cod_depositor_comments
'Adding full bibliography for 4135364--4135366.cif.'
_cod_database_code               4135365
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.885
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              3205
_shelx_hkl_checksum              31668
_shelx_fab_checksum              2874
_olex2_submission_special_instructions 'No special instructions were received'