Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source.
Woerly, Eric M.; Banik, Steven M.; Jacobsen, Eric N.; Journal of the American Chemical Society 138 (2016) 13858–13861; doi:10.1021/jacs.6b09499

data_4131121
_publ_section_title
;
 Enantioselective, Catalytic Fluorolactonization Reactions with a
 Nucleophilic Fluoride Source.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13858
_journal_page_last               13861
_journal_paper_doi               10.1021/jacs.6b09499
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H12 Cl F O2'
_chemical_formula_weight         242.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 123.3915(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6152(6)
_cell_length_b                   4.31270(10)
_cell_length_c                   14.1504(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      3.74
_cell_volume                     1101.35(5)
_computing_cell_refinement       'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT 8.34C (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12210
_diffrn_reflns_point_group_measured_fraction_full 0.900
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.722
_diffrn_reflns_theta_min         3.741
_exptl_absorpt_coefficient_mu    3.063
_exptl_absorpt_correction_T_max  0.8058
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0221
_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^)+(0.0339P)^2^+0.6658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0592
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.793
_reflns_Friedel_fraction_max     0.791
_reflns_number_gt                1734
_reflns_number_total             1747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09499_si_003.cif
_cod_data_source_block           EMW-456A-IV-37
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4131121
_shelx_estimated_absorpt_t_min   0.503
_shelx_estimated_absorpt_t_max   0.710
_refine_ls_abs_structure_hooft   0.011(6)
_shelxl_version_number           2014/6
_shelx_res_checksum              21179
_shelx_hkl_checksum              77602