Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids.
Yu, Jin-Sheng; Espinosa, Miguel; Noda, Hidetoshi; Shibasaki, Masakatsu; Journal of the American Chemical Society 141 (2019) 10530–10537; doi:10.1021/jacs.9b05476

data_4128042
_publ_section_title
;
 Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic
 \b-Amino Acids.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10530
_journal_page_last               10537
_journal_paper_doi               10.1021/jacs.9b05476
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C10 H10 F N O2'
_chemical_formula_sum            'C10 H10 F N O2'
_chemical_formula_weight         195.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 133.858(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7185(5)
_cell_length_b                   9.30450(10)
_cell_length_c                   12.4912(3)
_cell_measurement_reflns_used    12785
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.3920
_cell_measurement_theta_min      5.6080
_cell_volume                     1736.31(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -89.00 -12.00   0.50    0.05    --  -47.95 113.00  36.00  154
  2  \w      6.00  89.00   0.50    0.05    --   47.95-113.00 -55.00  166
  3  \w   -111.00 -27.00   0.50    0.07    -- -100.00 113.00  36.00  168
  4  \w   -173.00 -86.00   0.50    0.07    -- -100.00-113.00 -55.00  174
  5  \w     80.00 174.00   0.50    0.07    --  106.49 113.00  36.00  188
  6  \w     34.00 112.00   0.50    0.07    --  106.49-113.00 -55.00  156
  7  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 120.00  190
  8  \w    -60.00  25.00   0.50    0.05    --  -47.95  38.00  60.00  170
  9  \w     73.00 120.00   0.50    0.05    --   47.95 125.00 -30.00   94
 10  \w     73.00 120.00   0.50    0.05    --   47.95 125.00-120.00   94
 11  \w     25.00 120.00   0.50    0.05    --   47.95  77.00  60.00  190
 12  \w   -114.00 -25.00   0.50    0.07    -- -100.00  15.00-150.00  178
 13  \w   -114.00 -25.00   0.50    0.07    -- -100.00  15.00  60.00  178
 14  \w    -81.00 -28.00   0.50    0.07    -- -100.00  45.00 -60.00  106
 15  \w   -123.00 -27.00   0.50    0.07    -- -100.00  77.00-150.00  192
 16  \w   -117.00 -27.00   0.50    0.07    -- -100.00 125.00-180.00  180
 17  \w    -67.00 -25.00   0.50    0.07    -- -100.00  30.00  60.00   84
 18  \w   -117.00 -27.00   0.50    0.07    -- -100.00 125.00  60.00  180
 19  \w    -67.00 -25.00   0.50    0.07    -- -100.00  30.00  90.00   84
 20  \w    -81.00 -28.00   0.50    0.07    -- -100.00  45.00-150.00  106
 21  \w     35.00  75.00   0.50    0.07    --  106.49 -45.00 -90.00   80
 22  \w     94.00 174.00   0.50    0.07    --  106.49  45.00-180.00  160
 23  \w     32.00  61.00   0.50    0.07    --  106.49 -30.00  90.00   58
 24  \w     94.00 174.00   0.50    0.07    --  106.49  45.00 120.00  160
 25  \w     34.00 108.00   0.50    0.07    --  106.49 -94.00-120.00  148
 26  \w     34.00 123.00   0.50    0.07    --  106.49 -61.00 -90.00  178
 27  \w     34.00 108.00   0.50    0.07    --  106.49 -94.00 -30.00  148
 28  \w     35.00  75.00   0.50    0.07    --  106.49 -45.00 -30.00   80
 29  \w     34.00 108.00   0.50    0.07    --  106.49 -94.00-150.00  148
 30  \w     32.00  61.00   0.50    0.07    --  106.49 -30.00  60.00   58
 31  \w     25.00 120.00   0.50    0.05    --   47.95  77.00-150.00  190
 32  \w     33.00 119.00   0.50    0.05    --   47.95  57.00  30.00  172
 33  \w     33.00 119.00   0.50    0.05    --   47.95  57.00-180.00  172
 34  \w     33.00 119.00   0.50    0.05    --   47.95  57.00 -60.00  172
 35  \w     25.00 120.00   0.50    0.05    --   47.95  77.00  90.00  190
 36  \w     25.00 120.00   0.50    0.05    --   47.95  77.00 -60.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0046492000
_diffrn_orient_matrix_UB_12      0.1605750000
_diffrn_orient_matrix_UB_13      -0.0240116000
_diffrn_orient_matrix_UB_21      0.0881436000
_diffrn_orient_matrix_UB_22      -0.0265053000
_diffrn_orient_matrix_UB_23      0.0404095000
_diffrn_orient_matrix_UB_31      -0.0533369000
_diffrn_orient_matrix_UB_32      -0.0300674000
_diffrn_orient_matrix_UB_33      -0.1645054000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15715
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.562
_diffrn_reflns_theta_min         5.602
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+1.8351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1718
_reflns_number_total             1791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05476_si_002.cif
_cod_data_source_block           exp_127
_cod_original_cell_volume        1736.31(10)
_cod_database_code               4128042
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H F N O'
_chemical_oxdiff_usercomment     yu
_shelx_estimated_absorpt_t_max   0.824
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 N004(H004)
2.b Ternary CH refined with riding coordinates:
 C00B(H00D)
2.c Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00E(H00F,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00C), C00C(H00E)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              58070
_shelx_hkl_checksum              24406
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.843
_oxdiff_exptl_absorpt_empirical_full_min 0.395