Bench-stable imine surrogates for the one-pot and catalytic asymmetric synthesis of α-amino esters/ketones.
Xu, Huacheng; Nazli, Adila; Zou, Cheng; Wang, Zhi-Peng; He, Yun; Chemical communications (Cambridge, England) 56 (2020) 14243–14246; doi:10.1039/d0cc06055k

data_7127411
_publ_section_title
;
 Bench-stable imine surrogates for the one-pot and catalytic asymmetric
 synthesis of \a-amino esters/ketones.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14243
_journal_page_last               14246
_journal_paper_doi               10.1039/d0cc06055k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H23 Cl2 N O6'
_chemical_formula_sum            'C23 H23 Cl2 N O6'
_chemical_formula_weight         480.32
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2020-06-02 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   12.39590(15)
_cell_length_b                   12.39590(15)
_cell_length_c                   13.34104(13)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    293.07(10)
_cell_measurement_theta_max      71.6830
_cell_measurement_theta_min      4.1090
_cell_volume                     1775.32(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.07(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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   -106.00  -7.00   1.00    1.00    --  -35.97 -19.00 -60.00   99
  2  \w     24.00  90.00   1.00    1.00    --   35.97-126.00  90.00   66
  3  \w    -31.00  53.00   1.00    1.00    --   35.97 -57.00-120.00   84
  4  \w     91.00 176.00   1.00    3.00    --  107.97  45.00  90.00   85
  5  \w     38.00 112.00   1.00    3.00    --  107.97-112.00-180.00   74
  6  \w     41.00 126.00   1.00    3.00    --  107.97 -61.00-120.00   85
  7  \w     38.00 129.00   1.00    3.00    --  107.97 -30.00 -60.00   91
  8  \w   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00-180.00   88
  9  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00 -90.00   84
 10  \w   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
 11  \w     87.00 112.00   1.00    3.00    --  107.97  30.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1239942000
_diffrn_orient_matrix_UB_12      0.0362170000
_diffrn_orient_matrix_UB_13      -0.0529742000
_diffrn_orient_matrix_UB_21      0.0490297000
_diffrn_orient_matrix_UB_22      -0.0286446000
_diffrn_orient_matrix_UB_23      0.0966268000
_diffrn_orient_matrix_UB_31      -0.0530948000
_diffrn_orient_matrix_UB_32      -0.1358749000
_diffrn_orient_matrix_UB_33      -0.0345169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6370
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.759
_diffrn_reflns_theta_min         4.118
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (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    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0542
_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^)+(0.1089P)^2^+0.0371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    0.578
_reflns_Friedel_fraction_max     0.541
_reflns_number_gt                3413
_reflns_number_total             3530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06055k2.cif
_cod_data_source_block           zzl_200521
_cod_depositor_comments          'Adding full bibliography for 7127411.cif.'
_cod_original_cell_volume        1775.32(5)
_cod_database_code               7127411
_chemical_oxdiff_formula         'C23 H22 Cl2 N O6'
_reflns_odcompleteness_completeness 99.95
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C20(H20), C19(H19), C13(H13), C23(H23), C15(H15), C22(H22),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2020-05-21
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.657