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_7127790
_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         'C26 H20 F O2 P'
_chemical_formula_sum            'C26 H20 F O2 P'
_chemical_formula_weight         414.39
_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     direct
_audit_creation_date             2020-09-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2255(5)
_cell_length_b                   12.6121(7)
_cell_length_c                   18.2822(12)
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    293.57(10)
_cell_measurement_theta_max      68.4380
_cell_measurement_theta_min      4.2450
_cell_volume                     2127.2(2)
_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      293.57(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      9.00  37.00   1.00    1.00    --    0.00  57.00  30.00   28
  2  \w     36.00 121.00   1.00    1.00    --   54.00  57.00 120.00   85
  3  \w    149.00 176.00   1.00    1.50    --  108.00 111.00 150.00   27
  4  \w     48.00 133.00   1.00    1.50    --  108.00 -77.00  60.00   85
  5  \w    105.00 133.00   1.00    1.50    --  108.00 -38.00-120.00   28
  6  \w     37.00  77.00   1.00    1.50    --  108.00 -38.00-120.00   40
  7  \w     24.00  66.00   1.00    1.00    --   54.00-125.00-150.00   42
  8  \w     23.00  54.00   1.00    1.00    --   54.00-125.00 -90.00   31
  9  \w    -19.00  16.00   1.00    1.00    --    0.00 -57.00-120.00   35
 10  \w    -69.00 -37.00   1.00    1.00    --    0.00 -57.00-120.00   32
 11  \w      2.00  56.00   1.00    1.00    --   54.00 -99.00 120.00   54
 12  \w     38.00 125.00   1.00    1.50    --  108.00 -38.00 150.00   87
 13  \w    100.00 146.00   1.00    1.50    --  108.00 111.00-120.00   46
;
_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      -0.0471230000
_diffrn_orient_matrix_UB_12      0.0654028000
_diffrn_orient_matrix_UB_13      -0.0670771000
_diffrn_orient_matrix_UB_21      -0.0961290000
_diffrn_orient_matrix_UB_22      -0.0925535000
_diffrn_orient_matrix_UB_23      -0.0257299000
_diffrn_orient_matrix_UB_31      -0.1279863000
_diffrn_orient_matrix_UB_32      0.0454973000
_diffrn_orient_matrix_UB_33      0.0442008000
_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  0.0285
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5258
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        66.565
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_min         4.259
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78875
_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    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.269
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0810
_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^)+(0.1530P)^2^+1.0880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2369
_reflns_Friedel_coverage         0.436
_reflns_Friedel_fraction_full    0.582
_reflns_Friedel_fraction_max     0.582
_reflns_number_gt                2726
_reflns_number_total             3076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07770d2.cif
_cod_data_source_block           xieshl_245-91
_cod_depositor_comments
'Adding full bibliography for 7127787--7127794.cif.'
_cod_database_code               7127790
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.863
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C4(H4), C5(H5), C6(H6), C10(H10), C14(H14), C13(H13),
 C12(H12), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
3.b Fitted hexagon refined as free rotating group:
 C7(C8,C3,C4,C5,C6), C10(C9,C14,C13,C12,C11)
;
_shelx_res_checksum              17676
_olex2_date_sample_data_collection 2020-09-25
_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.778