Ni-Catalyzed Asymmetric Hydrophosphinylation of Conjugated Enynes and Mechanistic Studies
Zhang, Ya-Qian; Zhang, Qingwei; Han, Xue-Yu; Wu, Yue; Qi, Peng-Jia; Zhang, Qing; Chemical Science  (2022) –; doi:10.1039/D2SC00091A

data_1566591
_publ_section_title
;
 Ni-Catalyzed Asymmetric Hydrophosphinylation of Conjugated Enynes and
 Mechanistic Studies
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00091A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H25 O2 P'
_chemical_formula_sum            'C25 H25 O2 P'
_chemical_formula_weight         388.42
_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     direct
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.89107(7)
_cell_length_b                   16.00327(17)
_cell_length_c                   22.3169(2)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.9680
_cell_measurement_theta_min      3.9510
_cell_volume                     2103.96(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      291(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00 -17.00   1.00    4.00    --  -41.05 -38.00-180.00   98
  2  \w   -115.00 -17.00   1.00    4.00    --  -41.05 -38.00-150.00   98
  3  \w      1.00  82.00   1.00    4.00    --   41.05 -99.00  60.00   81
  4  \w     26.00 118.00   1.00    8.00    --   99.68-125.00 -60.00   92
  5  \w     74.00 173.00   1.00    8.00    --   99.68  45.00 -60.00   99
  6  \w     94.00 173.00   1.00    8.00    --   99.68 125.00 120.00   79
  7  \w     27.00 126.00   1.00    8.00    --   99.68 -45.00 120.00   99
  8  \w     74.00 173.00   1.00    8.00    --   99.68  45.00-180.00   99
  9  \w     94.00 173.00   1.00    8.00    --   99.68 125.00-120.00   79
 10  \w   -113.00 -13.00   1.00    4.00    --  -41.05 -57.00  60.00  100
 11  \w   -113.00 -13.00   1.00    4.00    --  -41.05 -57.00 -30.00  100
 12  \w     74.00 173.00   1.00    8.00    --   99.68  45.00  90.00   99
 13  \w     67.00  92.00   1.00    8.00    --   99.68  77.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0226253000
_diffrn_orient_matrix_UB_12      0.0086359000
_diffrn_orient_matrix_UB_13      0.0684940000
_diffrn_orient_matrix_UB_21      -0.0036930000
_diffrn_orient_matrix_UB_22      -0.0958468000
_diffrn_orient_matrix_UB_23      0.0063080000
_diffrn_orient_matrix_UB_31      0.2605131000
_diffrn_orient_matrix_UB_32      -0.0021237000
_diffrn_orient_matrix_UB_33      -0.0058591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.068
_diffrn_reflns_theta_min         3.398
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0785P)^2^+0.3844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3754
_reflns_number_total             3919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00091a2.cif
_cod_data_source_block           zyq-0909
_cod_database_code               1566591
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         C20H20P1O2
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C7(H7), C3(H3), C17(H17), C2(H2), C15(H15), C6(H6), C14(H14),
 C20(H20), C5(H5), C24(H24), C22(H22), C23(H23), C21(H21), C9(H9)
2.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.729