Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride: Enantioselective Synthesis of β-Fluoroamines.
Pupo, Gabriele; Vicini, Anna Chiara; Ascough, David M. H.; Ibba, Francesco; Christensen, Kirsten E.; Thompson, Amber L.; Brown, John M.; Paton, Robert S.; Gouverneur, Véronique; Journal of the American Chemical Society 141 (2019) 2878–2883; doi:10.1021/jacs.8b12568

data_4128506
_publ_section_title
;
 Hydrogen Bonding Phase-Transfer Catalysis with Potassium Fluoride:
 Enantioselective Synthesis of \b-Fluoroamines.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2878
_journal_page_last               2883
_journal_paper_doi               10.1021/jacs.8b12568
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H23 F N, Cl, 2(H2 O)'
_chemical_formula_sum            'C19 H27 Cl F N O2'
_chemical_formula_weight         355.88
_chemical_melting_point          ?
_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_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-21
_audit_creation_method           CRYSTALS_ver_14.61_build_7005
_cell_angle_alpha                90
_cell_angle_beta                 99.750(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8499(6)
_cell_length_b                   17.9444(8)
_cell_length_c                   12.0116(7)
_cell_measurement_reflns_used    2800
_cell_measurement_temperature    300
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2
_cell_volume                     1879.96(19)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.071
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15443
_diffrn_reflns_theta_full        25.112
_diffrn_reflns_theta_max         29.896
_diffrn_reflns_theta_min         1.720
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             759.995
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1963 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.18(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         5692
_refine_ls_number_restraints     513
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.0021310
_refine_ls_shift/su_mean         0.0002743
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.99P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2098
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1580
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              24
_reflns_limit_k_min              -25
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4458
_reflns_number_total             9432
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.13
_oxford_diffrn_Wilson_scale      0.04
_oxford_refine_ls_r_factor_ref   0.0840
_oxford_refine_ls_scale          5.30(11)
_oxford_reflns_number_all        9432
_oxford_structure_analysis_title 7029-VT-2-300K
_cod_data_source_file            ja8b12568_si_003.cif
_cod_data_source_block           2g-HCl-VT-300K
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C19 H27 Cl1 F1 N1 O2'
_cod_database_code               4128506
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.16(8)
_oxford_bijvoet_difference       0.18(7)
_oxford_refined_flack_x          0.16(13)