Catalytic Asymmetric Access to Noncanonical Chiral α-Amino Acids from Cyclic Iminoglyoxylates and Enamides.
Zhang, Yue; Li, Jun-Kuan; Zhang, Fa-Guang; Ma, Jun-An; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00436

data_4038194
_publ_section_title
;
 Catalytic Asymmetric Access to Noncanonical Chiral \a-Amino Acids from
 Cyclic Iminoglyoxylates and Enamides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00436
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 Cl N O3'
_chemical_formula_sum            'C24 H20 Cl N O3'
_chemical_formula_weight         405.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.416(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2465(3)
_cell_length_b                   7.9689(3)
_cell_length_c                   13.2794(6)
_cell_measurement_reflns_used    6850
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      28.7100
_cell_measurement_theta_min      2.2180
_cell_volume                     965.30(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.839
_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      4.00  30.00   0.50    3.00    --    5.07 -98.00  -8.00   52
  2  \w      5.00  30.00   0.50    3.00    --    5.07  98.00  98.00   50
  3  \w    -25.00  40.00   0.50    3.00    --    5.07 -99.00 -60.00  130
  4  \w    -18.00   8.00   0.50    3.00    --    5.07 -99.00-150.00   52
  5  \w     -8.00  79.00   0.50    3.00    --    5.07  37.00 -60.00  174
  6  \w    -23.00  24.00   0.50    3.00    --   -6.71 -99.00  90.00   94
  7  \w    -22.00   5.00   0.50    3.00    --   -6.79 -98.00  -9.00   54
  8  \w    -61.00   2.00   0.50    3.00    --   -6.79 -57.00-120.00  126
  9  \w    -26.00   0.00   0.50    3.00    --   -6.79 -99.00 -30.00   52
 10  \w    -78.00  -7.00   0.50    3.00    --   -6.79 -77.00  60.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0515337000
_diffrn_orient_matrix_UB_12      0.0599082000
_diffrn_orient_matrix_UB_13      -0.0116720000
_diffrn_orient_matrix_UB_21      -0.0265090000
_diffrn_orient_matrix_UB_22      0.0588611000
_diffrn_orient_matrix_UB_23      0.0326806000
_diffrn_orient_matrix_UB_31      0.0518152000
_diffrn_orient_matrix_UB_32      -0.0295113000
_diffrn_orient_matrix_UB_33      0.0415601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.794
_diffrn_reflns_theta_min         2.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0413P)^2^+0.0496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                4052
_reflns_number_total             4868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00436_si_002.cif
_cod_data_source_block           zy_346_1b
_cod_database_code               4038194
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C22(H22), C18(H18), C24(H24), C14(H14), C20(H20), C23(H23), C2(H2),
 C15(H15), C17(H17), C16(H16), C21(H21), C3(H3), C4(H4)
;
_shelx_res_checksum              83469
_shelx_hkl_checksum              4470
_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 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.892