Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions.
Okoromoba, Otome E.; Li, Zhou; Robertson, Nicole; Mashuta, Mark S.; Couto, Uenifer R.; Tormena, Cláudio F; Xu, Bo; Hammond, Gerald B.; Chemical communications (Cambridge, England) 52 (2016) 13353–13356; doi:10.1039/c6cc07855a

data_7125246
_publ_section_title
;
 Achieving regio- and stereo-control in the fluorination of aziridines
 under acidic conditions.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13353
_journal_page_last               13356
_journal_paper_doi               10.1039/c6cc07855a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 F N O2 S'
_chemical_formula_sum            'C16 H18 F N O2 S'
_chemical_formula_weight         307.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-07-01 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2947(3)
_cell_length_b                   9.5293(2)
_cell_length_c                   18.8749(4)
_cell_measurement_reflns_used    8576
_cell_measurement_temperature    99.9(1)
_cell_measurement_theta_max      29.7300
_cell_measurement_theta_min      3.8760
_cell_volume                     1491.92(7)
_computing_cell_refinement       '<i>CrysAlis PRO</i> (Agilent, 2013)'
_computing_data_collection       '<i>CrysAlis PRO</i> (Agilent, 2013)'
_computing_data_reduction        '<i>CrysAlis PRO</i> (Agilent, 2013)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae<i>et al.</i>, 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  '<i>SHELXL-97</i> (Sheldrick, 2008)'
_computing_structure_solution    '<i>SHELXS-97</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.9(1)
_diffrn_detector_area_resol_mean 10.2836
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -92.00    0.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196  -77.0000 -120.0000 92

  2 omega  -46.00   39.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7321  -57.0000  -90.0000 85

  3 omega  -92.00   20.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196  -77.0000   90.0000 112

  4 omega  -43.00    9.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196   57.0000   30.0000 52

  5 omega  -60.00   15.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7321  -57.0000  150.0000 75

;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16718
_diffrn_reflns_theta_full        28.06
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.3 SCALE3 ABSPACK
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
; 
Flack H D (1983), Acta Cryst. A39, 876-881
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+0.7605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0752
_reflns_number_gt                3373
_reflns_number_total             3614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc07855a2.cif
_cod_data_source_block           gbh35lta_S2d
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_database_code               7125246