Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines.
Roagna, Giulia; Ascough, David M. H.; Ibba, Francesco; Vicini, Anna Chiara; Fontana, Alberto; Christensen, Kirsten E.; Peschiulli, Aldo; Oehlrich, Daniel; Misale, Antonio; Trabanco, Andrés A; Paton, Robert S.; Pupo, Gabriele; Gouverneur, Veronique; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c05131

data_4135144
_publ_section_title
;
 Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants:
 Enantioselective Synthesis of \g-Fluoroamines.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c05131
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H17 F1 N, Cl'
_chemical_formula_sum            'C11 H17 Cl F N'
_chemical_formula_weight         217.71
_chemical_melting_point          ?
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2019-07-15
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.95040(10)
_cell_length_b                   10.52650(10)
_cell_length_c                   23.7547(4)
_cell_measurement_reflns_used    18010
_cell_measurement_temperature    300
_cell_measurement_theta_max      76.91
_cell_measurement_theta_min      3.72
_cell_volume                     2488.14(5)
_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    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_av_unetI/netI     0.052
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            49083
_diffrn_reflns_theta_full        77.272
_diffrn_reflns_theta_max         77.272
_diffrn_reflns_theta_min         3.721
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.544
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_correction_T_min  0.41
_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    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928.000
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.12
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 2145 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5262
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.0006166
_refine_ls_shift/su_mean         0.0000456
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.09P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0997
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0997
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                4695
_reflns_number_total             5262
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.77
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.0382
_oxford_refine_ls_scale          4.41(6)
_oxford_reflns_number_all        5262
_oxford_structure_analysis_title 'exp_4468_2_300_00 -7146-CU'
_cod_data_source_file            ja0c05131_si_003.cif
_cod_data_source_block           (R)-3ab-HCl
_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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C11 H17 Cl F1 N'
_cod_database_code               4135144
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  -0.005(7)
_oxford_bijvoet_difference       0.001(6)
_oxford_refined_flack_x          0.007(13)