Synthesis of <i>N</i><i> <sub>β</sub> </i>-Substituted α,β-Diamino Acids via Stereoselective <i>N</i>-Michael Additions to a Chiral Bicyclic Dehydroalanine.
Navo, Claudio D.; Mazo, Nuria; Oroz, Paula; Gutiérrez-Jiménez, Marta I; Marín, Javier; Asenjo, Juan; Avenoza, Alberto; Busto, Jesús H; Corzana, Francisco; Zurbano, María M; Jiménez-Osés, Gonzalo; Peregrina, Jesús M; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03020

data_4037944
_publ_section_title
;
 Synthesis of <i>N</i><i> <sub>\b</sub> </i>-Substituted \a,\b-Diamino
 Acids via Stereoselective <i>N</i>-Michael Additions to a Chiral Bicyclic
 Dehydroalanine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03020
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H29 N3 O5'
_chemical_formula_sum            'C23 H29 N3 O5'
_chemical_formula_weight         427.49
_chemical_name_common            JA-TFG-1
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-04-27T13:44:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.483(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0249(11)
_cell_length_b                   7.4099(6)
_cell_length_c                   13.5550(12)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24.877
_cell_measurement_theta_min      4.03
_cell_measurement_wavelength     0.71076
_cell_volume                     1107.76(17)
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.064081
_diffrn_orient_matrix_UB_12      0.095445
_diffrn_orient_matrix_UB_13      0.023953
_diffrn_orient_matrix_UB_21      -0.020141
_diffrn_orient_matrix_UB_22      0.026746
_diffrn_orient_matrix_UB_23      0.063309
_diffrn_orient_matrix_UB_31      0.060902
_diffrn_orient_matrix_UB_32      -0.091582
_diffrn_orient_matrix_UB_33      0.043452
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         33.497
_diffrn_reflns_theta_min         2.917
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
	[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            'translucent pale colourless'
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.05
_refine_ls_abs_structure_details
;
 Flack x determined using 3097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     296
_refine_ls_number_reflns         8516
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.0389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.97
_reflns_number_gt                7284
_reflns_number_total             8516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03020_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037944
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.982