Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes.
Talbot, Eric P. A.; Fernandes, Talita de A; McKenna, Jeffrey M.; Toste, F. Dean; Journal of the American Chemical Society 136 (2014) 4101–4104; doi:10.1021/ja412881j

data_4121476
_publ_section_title
;
 Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of
 styrenes.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4101
_journal_page_last               4104
_journal_paper_doi               10.1021/ja412881j
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H17 Br F N O'
_chemical_formula_weight         398.27
_chemical_name_common            TAF89C
_chemical_name_systematic
; 
 toste97 
;
_space_group.centring_type       P
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 92.918(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0571(2)
_cell_length_b                   21.8253(8)
_cell_length_c                   15.7019(6)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.27
_cell_volume                     1730.81(11)
_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
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         0.5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
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_diffrn_reflns_number            21571
_diffrn_reflns_point_group_measured_fraction_full 0.969
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_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.389
_diffrn_reflns_theta_min         1.599
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.018(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0145P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0518
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                5518
_reflns_number_total             6104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja412881j_si_002.cif
_cod_data_source_block           toste97
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4121476
_shelx_estimated_absorpt_t_min   0.870
_shelx_estimated_absorpt_t_max   0.954
_shelxl_version_number           2014-1
_shelx_res_checksum              20436
_shelx_hkl_checksum              70142