The development and mechanistic investigation of a palladium-catalyzed 1,3-arylfluorination of chromenes.
Thornbury, Richard T.; Saini, Vaneet; Fernandes, Talita de A; Santiago, Celine B.; Talbot, Eric P. A.; Sigman, Matthew S.; McKenna, Jeffrey M.; Toste, F. Dean; Chemical science 8 (2017) 2890–2897; doi:10.1039/c6sc05102b

data_1545242
_publ_section_title
;
 The development and mechanistic investigation of a palladium-catalyzed
 1,3-arylfluorination of chromenes.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              2890
_journal_page_last               2897
_journal_paper_doi               10.1039/c6sc05102b
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         C22H17BrFNO2
_chemical_formula_sum            'C22 H17 Br F N O2'
_chemical_formula_weight         426.27
_chemical_name_systematic
4-(4-bromophenyl)-2-fluoro-N-phenylchromane-5-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-11-21 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.552(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3026(6)
_cell_length_b                   12.0184(4)
_cell_length_c                   10.1214(4)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      2.89
_cell_volume                     1861.37(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir-2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24648
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.325
_diffrn_reflns_theta_min         2.888
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    3.238
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Pentane'
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0448P)^2^+2.6265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2939
_reflns_number_total             3399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc05102b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for 1545242.cif.

 Adding full bibliography for 1545242.cif.
;
_cod_database_code               1545242
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2014-1
_shelx_res_checksum              40762