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_4035912
_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_formula_moiety         'C22 H19 F N2 O3'
_chemical_formula_sum            'C22 H19 F N2 O3'
_chemical_formula_weight         378.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                93.627(18)
_cell_angle_beta                 99.834(18)
_cell_angle_gamma                93.558(16)
_cell_formula_units_Z            2
_cell_length_a                   6.9619(14)
_cell_length_b                   9.2892(19)
_cell_length_c                   15.045(4)
_cell_measurement_reflns_used    1005
_cell_measurement_temperature    291.93(10)
_cell_measurement_theta_max      22.6070
_cell_measurement_theta_min      3.8200
_cell_volume                     954.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      291.93(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -6.00   24.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   30.0000 15

  2 omega  -92.00  -14.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -77.0000    0.0000 39

  3 omega   -2.00   26.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000 -120.0000 14

  4 omega  -45.00   47.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 46

  5 omega  -47.00   27.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000   30.0000 37

  6 omega   -1.00   93.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -90.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0564695000
_diffrn_orient_matrix_UB_12      0.0575100000
_diffrn_orient_matrix_UB_13      0.0276658000
_diffrn_orient_matrix_UB_21      0.0311039000
_diffrn_orient_matrix_UB_22      0.0269357000
_diffrn_orient_matrix_UB_23      -0.0386916000
_diffrn_orient_matrix_UB_31      -0.0812078000
_diffrn_orient_matrix_UB_32      0.0430494000
_diffrn_orient_matrix_UB_33      -0.0063278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6161
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.40
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                1990
_reflns_number_total             3747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02316_si_004.cif
_cod_data_source_block           liangh_0914
_cod_database_code               4035912
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_olex2_date_sample_data_collection 2017-09-15
_olex2_submission_special_instructions 'No special instructions were received'