Role of imine isomerization in the stereocontrol of the Staudinger reaction between ketenes and imines.
Cossío, Fernando P; de Cózar, Abel; Sierra, Miguel A.; Casarrubios, Luis; Muntaner, Jaime G.; Banik, Bimal K.; Bandyopadhyay, Debasish; RSC advances 12 (2021) 104–117; doi:10.1039/d1ra06114c

data_7244094
_publ_section_title
;
 Role of imine isomerization in the stereocontrol of the Staudinger
 reaction between ketenes and imines.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              104
_journal_page_last               117
_journal_paper_doi               10.1039/d1ra06114c
_journal_volume                  12
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-10-07T12:05:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-09-04 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.303(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9199(12)
_cell_length_b                   20.1342(16)
_cell_length_c                   8.5465(9)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9296
_cell_measurement_theta_min      2.8498
_cell_measurement_wavelength     0.71073
_cell_volume                     1794.0(3)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_molecular_graphics    'Diamond v.3.1f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3504
_diffrn_detector_type            'Sapphire2 (large Be window)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -17.00  106.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       22.2103   37.0000  120.0000 123

  2 omega   30.00   60.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       22.2103  -77.0000   30.0000 30

  3 omega    6.00   97.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       22.2103   77.0000  -30.0000 91

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0795574857
_diffrn_orient_matrix_UB_12      0.0004153097
_diffrn_orient_matrix_UB_13      0.0445334098
_diffrn_orient_matrix_UB_21      -0.0350528634
_diffrn_orient_matrix_UB_22      -0.0014199223
_diffrn_orient_matrix_UB_23      0.051332122
_diffrn_orient_matrix_UB_31      0.0027946395
_diffrn_orient_matrix_UB_32      -0.035192605
_diffrn_orient_matrix_UB_33      -0.0010187754
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7395
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.65871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
        (compiled Sep 15 2009,11:49:04)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.3565(2)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut prism'
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                2256
_reflns_number_total             3671
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d1ra06114c2.cif
_cod_data_source_block           maria2
_cod_depositor_comments
'Adding full bibliography for 7244093--7244094.cif.'
_cod_database_code               7244094