Dual Catalytic Switchable Divergent Synthesis: An Asymmetric Visible-Light Photocatalytic Approach to Fluorine-Containing γ-Keto Acid Frameworks.
Liang, Hui; Xu, Guo-Qiang; Feng, Zhi-Tao; Wang, Zhu-Yin; Xu, Peng-Fei; The Journal of organic chemistry 84 (2019) 60–72; doi:10.1021/acs.joc.8b02316

data_4035911
_publ_section_title
;
 Dual Catalytic Switchable Divergent Synthesis: An Asymmetric
 Visible-Light Photocatalytic Approach to Fluorine-Containing \g-Keto Acid
 Frameworks.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              60
_journal_page_last               72
_journal_paper_doi               10.1021/acs.joc.8b02316
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H22 F N3 O3'
_chemical_formula_sum            'C23 H22 F N3 O3'
_chemical_formula_weight         407.44
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.00151(15)
_cell_length_b                   9.9401(3)
_cell_length_c                   29.1848(8)
_cell_measurement_reflns_used    3093
_cell_measurement_temperature    293.19(10)
_cell_measurement_theta_max      69.7430
_cell_measurement_theta_min      4.6860
_cell_volume                     2031.14(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.19(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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    -15.00  65.00   1.00    1.00    --    0.00  57.00 -90.00   80
  2  \w    -83.00 -53.00   1.00    1.00    --   -8.50 178.00  60.00   30
  3  \w     32.00 123.00   1.00    1.00    --   54.00  57.00-120.00   91
  4  \w     41.00  68.00   1.00    1.00    --   54.00  57.00-180.00   27
  5  \w     77.00 107.00   1.00    1.00    --   54.00-125.00 -60.00   30
  6  \w     30.00  63.00   1.00    1.00    --   54.00-125.00 -60.00   33
  7  \w     39.00  92.00   1.00    1.00    --  108.00 -38.00 -60.00   53
  8  \w     53.00  99.00   1.00    1.00    --  108.00-111.00 120.00   46
  9  \w     68.00 104.00   1.00    1.00    --  108.00 -50.00 -30.00   36
 10  \w     39.00  91.00   1.00    1.00    --  108.00 -38.00  30.00   52
 11  \w    105.00 175.00   1.00    1.00    --  108.00  63.00 -60.00   70
 12  \w     36.00  61.00   1.00    1.00    --  108.00 -91.00-150.00   25
 13  \w    103.00 129.00   1.00    1.00    --  108.00 -91.00-150.00   26
 14  \w     74.00 122.00   1.00    1.00    --  108.00 -63.00  60.00   48
 15  \w     35.00 171.00   1.00    1.00    --  108.00 -12.00 150.00  136
;
_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      0.0577050000
_diffrn_orient_matrix_UB_12      0.1351377000
_diffrn_orient_matrix_UB_13      0.0218268000
_diffrn_orient_matrix_UB_21      -0.0484017000
_diffrn_orient_matrix_UB_22      0.0730355000
_diffrn_orient_matrix_UB_23      -0.0450798000
_diffrn_orient_matrix_UB_31      -0.2067561000
_diffrn_orient_matrix_UB_32      0.0206278000
_diffrn_orient_matrix_UB_33      0.0166496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6747
_diffrn_reflns_theta_full        69.66
_diffrn_reflns_theta_max         69.66
_diffrn_reflns_theta_min         4.70
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.1957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                3372
_reflns_number_total             3675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02316_si_003.cif
_cod_data_source_block           lianghui_0321
_cod_original_cell_volume        2031.15(9)
_cod_database_code               4035911
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_olex2_date_sample_data_collection 2018-03-22
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.634