Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral β-Amino Acids via Trapping of an Enol Intermediate.
Kang, Zhenghui; Wang, Yongheng; Zhang, Dan; Wu, Ruibo; Xu, Xinfang; Hu, Wenhao; Journal of the American Chemical Society 141 (2019) 1473–1478; doi:10.1021/jacs.8b12832

data_4128080
_publ_section_title
;
 Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral
 \b-Amino Acids via Trapping of an Enol Intermediate.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1473
_journal_page_last               1478
_journal_paper_doi               10.1021/jacs.8b12832
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C15 H17 Ag O11'
_chemical_formula_sum            'C15 H17 Ag O11'
_chemical_formula_weight         481.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                107.990(4)
_cell_angle_beta                 100.432(3)
_cell_angle_gamma                104.927(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8042(3)
_cell_length_b                   10.5315(4)
_cell_length_c                   10.8818(4)
_cell_measurement_reflns_used    5934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8500
_cell_measurement_theta_min      4.4390
_cell_volume                     889.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -30.00   1.00   1.00    1.00    --    0.00  79.00-168.00   31
  2  \w      7.00  48.00   1.00    1.00    --    0.00  79.00-168.00   41
  3  \w     79.00 127.00   1.00    1.00    --   95.80 -79.00  66.00   48
  4  \w     83.00 177.00   1.00    1.00    --   95.80  79.00-168.00   94
  5  \w    -88.00  17.00   1.00    1.00    --    0.00 -38.00-180.00  105
  6  \w    -89.00 -19.00   1.00    1.00    --    0.00 -19.00 120.00   70
  7  \w     11.00  37.00   1.00    1.00    --    0.00  38.00  60.00   26
  8  \w    -48.00  -1.00   1.00    1.00    --    0.00 -79.00  66.00   47
  9  \w      6.00  67.00   1.00    1.00    --   95.80 -82.00 -30.00   61
 10  \w     80.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00   48
 11  \w      6.00  56.00   1.00    1.00    --   95.80 -15.00-120.00   50
 12  \w     91.00 117.00   1.00    1.00    --   95.80 -82.00-180.00   26
 13  \w      7.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  121
 14  \w    109.00 135.00   1.00    1.00    --   95.80  30.00-180.00   26
 15  \w     13.00 116.00   1.00    1.00    --   95.80 -61.00   0.00  103
 16  \w      8.00  34.00   1.00    1.00    --   95.80 -82.00-120.00   26
 17  \w     38.00  69.00   1.00    1.00    --   95.80 -82.00-120.00   31
 18  \w     76.00 126.00   1.00    1.00    --   95.80 -82.00-120.00   50
 19  \w     76.00 106.00   1.00    1.00    --   95.80  61.00  30.00   30
 20  \w      7.00  69.00   1.00    1.00    --   95.80 -82.00-180.00   62
 21  \w     75.00 184.00   1.00    1.00    --   95.80  45.00 150.00  109
 22  \w    140.00 166.00   1.00    1.00    --   95.80  61.00  30.00   26
 23  \w     83.00 181.00   1.00    1.00    --   95.80  77.00-150.00   98
 24  \w     91.00 116.00   1.00    1.00    --   95.80 -77.00 -90.00   25
 25  \w     59.00  85.00   1.00    1.00    --   95.80 -15.00-120.00   26
 26  \w     96.00 122.00   1.00    1.00    --   95.80 -82.00  30.00   26
 27  \w     26.00  67.00   1.00    1.00    --   95.80 -45.00-120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0968115000
_diffrn_orient_matrix_UB_12      0.0637179000
_diffrn_orient_matrix_UB_13      -0.0825432000
_diffrn_orient_matrix_UB_21      0.1030099000
_diffrn_orient_matrix_UB_22      0.1500624000
_diffrn_orient_matrix_UB_23      0.1027663000
_diffrn_orient_matrix_UB_31      0.1252156000
_diffrn_orient_matrix_UB_32      0.0083318000
_diffrn_orient_matrix_UB_33      -0.0819722000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8630
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.455
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.797
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.771
_refine_diff_density_min         -1.752
_refine_diff_density_rms         0.189
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0691
_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^)+(0.1368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.1836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2822
_reflns_number_total             3144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b12832_si_003.cif
_cod_data_source_block           exp_377
_cod_original_cell_volume        889.19(6)
_cod_database_code               4128080
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11C,H11D,H11E), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              53316
_shelx_hkl_checksum              61857
_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 6.200
_oxdiff_exptl_absorpt_empirical_full_min 0.242