An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.
Zi, Weiwei; Wang, Yi-Ming; Toste, F. Dean; Journal of the American Chemical Society 136 (2014) 12864–12867; doi:10.1021/ja507468u

data_4122923
_publ_section_title
;
 An in situ directing group strategy for chiral anion phase-transfer
 fluorination of allylic alcohols.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12864
_journal_page_last               12867
_journal_paper_doi               10.1021/ja507468u
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H10 Br F O'
_chemical_formula_weight         245.09
_chemical_name_common            ZW05163
_chemical_name_systematic
; 
 toste107 
;
_space_group.centring_type       P
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9777(4)
_cell_length_b                   9.2119(7)
_cell_length_c                   21.6756(18)
_cell_measurement_reflns_used    3158
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.15
_cell_measurement_theta_min      5.22
_cell_volume                     993.91(14)
_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 0.985
_diffrn_measured_fraction_theta_max 0.973
_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  0.0784
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_refln_scan_rate          20
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11647
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_min         4.079
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    5.436
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         2.650
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.288
_refine_ls_abs_structure_details
; 
 Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.1034
_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^)+(0.1878P)^2^+2.0539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2596
_refine_ls_wR_factor_ref         0.2816
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                1275
_reflns_number_total             1699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja507468u_si_002.cif
_cod_data_source_block           toste107
_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               4122923
_shelx_estimated_absorpt_t_min   0.812
_shelx_estimated_absorpt_t_max   0.948
_shelxl_version_number           2014-3
_shelx_res_checksum              32845
_shelx_hkl_checksum              3485