Alpha-Fluorination of carbonyls with nucleophilic fluorine
Pauline Adler; Christopher J. Teskey; Daniel Kaiser; Marion Holy; Harald H. Sitte; Nuno Maulide; Nature Chemistry 11 (2019) 329–334; doi:10.1038/s41557-019-0215-z

data_1551355
_publ_section_title
;
 Alpha-Fluorination of carbonyls with nucleophilic fluorine
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              329
_journal_page_last               334
_journal_paper_doi               10.1038/s41557-019-0215-z
_journal_volume                  11
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H21 F2 N2 O, C18 H13 O8'
_chemical_formula_sum            'C38 H34 F2 N2 O9'
_chemical_formula_weight         700.67
_chemical_name_systematic
;      
(S)-3-((S)-5-cyano-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-1-yl)-2-fluoro-
N,N-dimethylpropan-1-aminium (2R,3R)-2,3-bis(benzoyloxy)-3-carboxypropanoate
;
_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'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 91.545(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4858(4)
_cell_length_b                   21.3740(12)
_cell_length_c                   21.5083(13)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.925
_cell_measurement_theta_min      2.686
_cell_volume                     3440.1(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            158993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_min         2.121
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'INCOATEC microfocus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_correction_T_min  0.8400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0762 before and 0.0574 after correction. 
The Ratio of minimum to maximum transmission is 0.9461. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 5593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     929
_refine_ls_number_reflns         20145
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0809
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+6.7272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1895
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                16076
_reflns_number_total             20145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            41557_2019_215_MOESM271_ESM.cif
_cod_data_source_block           paad991_p21
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1551355
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.992