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_4038193
_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 rmad
_chemical_formula_moiety         'C26 H24 N2 O3'
_chemical_formula_sum            'C26 H24 N2 O3'
_chemical_formula_weight         412.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4501(3)
_cell_length_b                   9.7777(3)
_cell_length_c                   23.5886(8)
_cell_measurement_reflns_used    9305
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.467
_cell_measurement_theta_min      4.895
_cell_volume                     2179.59(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23098
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         4.896
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1636 before and 0.0838 after correction. The Ratio of minimum to maximum transmission is 0.7619. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0682P)^2^+0.5872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4070
_reflns_number_total             4337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00436_si_004.cif
_cod_data_source_block           zz
_cod_database_code               4038193
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.949
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N28(H28), C5(H5), C17(H17), C20(H20), C13(H13), C3(H3), C4(H4), C9(H9),
 C1(H1), C2(H2), C12(H12), C10(H10), C21(H21), C24(H24), C11(H11), C22(H22),
 C23(H23)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'