The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters.
Xie, Shaolei; He, Zhi-Juan; Zhang, Ling-Hui; Huang, Bo-Lun; Chen, Xiao-Wei; Zhan, Zong-Song; Zhang, Fu-Min; Chemical communications (Cambridge, England) 57 (2021) 2069–2072; doi:10.1039/d0cc07770d

data_7127787
_publ_section_title
;
 The organocatalytic enantiodivergent fluorination of
 \b-ketodiaryl-phosphine oxides for the construction of carbon-fluorine
 quaternary stereocenters.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2069
_journal_page_last               2072
_journal_paper_doi               10.1039/d0cc07770d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 F O2 P'
_chemical_formula_sum            'C27 H22 F O2 P'
_chemical_formula_weight         428.41
_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     direct
_audit_creation_date             2020-09-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-09-30 deposited with the CCDC.	2020-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.467(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1721(4)
_cell_length_b                   9.7020(3)
_cell_length_c                   14.1513(6)
_cell_measurement_reflns_used    1673
_cell_measurement_temperature    294.82(10)
_cell_measurement_theta_max      66.0090
_cell_measurement_theta_min      9.2110
_cell_volume                     1316.75(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.82(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -24.00  11.00   1.00    1.00    --    0.00 106.00  69.00   35
  2  \w      4.00  67.00   1.00    1.00    --    0.00  77.00 -90.00   63
  3  \w     -8.00  95.00   1.00    2.00    --   54.00 -19.00 -90.00  103
  4  \w     85.00 178.00   1.00    4.00    --  108.00  38.00-180.00   93
  5  \w     88.00 127.00   1.00    4.00    --  108.00 -50.00 -30.00   39
  6  \w     89.00 116.00   1.00    4.00    --  108.00-111.00  90.00   27
  7  \w     62.00 136.00   1.00    4.00    --  108.00 -77.00   0.00   74
  8  \w     52.00 107.00   1.00    4.00    --  108.00-113.00-118.00   55
  9  \w     87.00 132.00   1.00    4.00    --  108.00 -77.00-180.00   45
 10  \w     65.00  91.00   1.00    2.00    --   54.00-125.00-180.00   26
 11  \w     36.00 124.00   1.00    4.00    --  108.00 -38.00-180.00   88
 12  \w     78.00 120.00   1.00    2.00    --   54.00  57.00-120.00   42
 13  \w    104.00 129.00   1.00    4.00    --  108.00 111.00  30.00   25
 14  \w    112.00 147.00   1.00    4.00    --  108.00 111.00 120.00   35
 15  \w    116.00 167.00   1.00    4.00    --  108.00  38.00 120.00   51
 16  \w    112.00 146.00   1.00    4.00    --  108.00 178.00 -90.00   34
 17  \w     70.00  96.00   1.00    4.00    --  108.00 178.00 -90.00   26
 18  \w     35.00 124.00   1.00    4.00    --  108.00 -25.00   0.00   89
 19  \w     49.00 130.00   1.00    4.00    --  108.00 -50.00  90.00   81
 20  \w     43.00  84.00   1.00    4.00    --  108.00 -50.00 -30.00   41
 21  \w     37.00 103.00   1.00    2.00    --   54.00-125.00  30.00   66
 22  \w     36.00 104.00   1.00    4.00    --  108.00-111.00   0.00   68
 23  \w     -1.00  84.00   1.00    2.00    --   54.00 -77.00  60.00   85
 24  \w    -11.00  80.00   1.00    2.00    --   54.00 -38.00  90.00   91
 25  \w    -15.00  11.00   1.00    2.00    --   54.00 -57.00  90.00   26
 26  \w    -33.00  19.00   1.00    1.00    --    0.00 -57.00 -30.00   52
 27  \w      1.00  73.00   1.00    2.00    --   54.00 -57.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286739000
_diffrn_orient_matrix_UB_12      0.1441526000
_diffrn_orient_matrix_UB_13      -0.0344956000
_diffrn_orient_matrix_UB_21      0.0369221000
_diffrn_orient_matrix_UB_22      0.0534070000
_diffrn_orient_matrix_UB_23      0.1082558000
_diffrn_orient_matrix_UB_31      0.1536435000
_diffrn_orient_matrix_UB_32      -0.0397839000
_diffrn_orient_matrix_UB_33      0.0206115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.578
_diffrn_reflns_theta_max         66.578
_diffrn_reflns_theta_min         4.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0354P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3642
_reflns_number_total             4657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07770d2.cif
_cod_data_source_block           xieshaol_0622
_cod_depositor_comments
'Adding full bibliography for 7127787--7127794.cif.'
_cod_original_cell_volume        1316.74(9)
_cod_database_code               7127787
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_res_checksum              97354
_shelx_fab_checksum              64213
_olex2_date_sample_data_collection 2020-06-22
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.719