Construction of chiral <i>N</i>,<i>O</i>-hemiaminals <i>via</i> a copper-catalyzed enantioselective Michael/<i>N</i>-hemiacetalization cascade reaction.
Li, Kuiliang; Gao, Siyu; Zha, Zhenggen; Wang, Zhiyong; Organic & biomolecular chemistry 21 (2023) 4404–4408; doi:10.1039/d3ob00542a

data_7159346
_publ_section_title
;
 Construction of chiral <i>N</i>,<i>O</i>-hemiaminals <i>via</i> a
 copper-catalyzed enantioselective Michael/<i>N</i>-hemiacetalization
 cascade reaction.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4404
_journal_page_last               4408
_journal_paper_doi               10.1039/d3ob00542a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H23 Br N2 O4'
_chemical_formula_sum            'C27 H23 Br N2 O4'
_chemical_formula_weight         519.38
_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   geom
_audit_creation_date             2022-09-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-10 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.19020(11)
_cell_length_b                   11.29931(13)
_cell_length_c                   21.3624(3)
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9670
_cell_measurement_theta_min      5.6950
_cell_volume                     2459.71(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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   -119.00  -3.00   1.00    2.00    --  -41.76 -19.00  60.00  116
  2  \w     10.00  44.00   1.00    2.00    --   41.76 -77.00 -90.00   34
  3  \w     55.00  93.00   1.00    2.00    --   41.76-125.00 -60.00   38
  4  \w    131.00 175.00   1.00    4.00    --  106.05  77.00 -30.00   44
  5  \w     82.00 112.00   1.00    4.00    --  106.05-125.00  90.00   30
  6  \w    107.00 154.00   1.00    4.00    --  106.05  77.00 -60.00   47
  7  \w     82.00 108.00   1.00    4.00    --  106.05-125.00-180.00   26
  8  \w     35.00 131.00   1.00    4.00    --  106.05 -61.00 -60.00   96
  9  \w     78.00 178.00   1.00    4.00    --  106.05  30.00 -90.00  100
 10  \w     34.00 104.00   1.00    4.00    --  106.05 -94.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0767851000
_diffrn_orient_matrix_UB_12      -0.1174167000
_diffrn_orient_matrix_UB_13      0.0001340000
_diffrn_orient_matrix_UB_21      0.1290210000
_diffrn_orient_matrix_UB_22      0.0686384000
_diffrn_orient_matrix_UB_23      0.0096930000
_diffrn_orient_matrix_UB_31      -0.0176629000
_diffrn_orient_matrix_UB_32      -0.0091083000
_diffrn_orient_matrix_UB_33      0.0714788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.992
_diffrn_reflns_theta_min         4.139
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0401P)^2^+0.7713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4696
_reflns_number_total             4766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00542a2.cif
_cod_data_source_block           lkl11_auto
_cod_depositor_comments          'Adding full bibliography for 7159346.cif.'
_cod_original_cell_volume        2459.72(5)
_cod_database_code               7159346
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20o2n2c
_shelx_estimated_absorpt_t_max   0.627
_shelx_estimated_absorpt_t_min   0.577
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C2(H2A), C3(H3), C21(H21), C15(H15), C18(H18),
 C22(H22), C16(H16), C25(H25), C17(H17), C23(H23), C24(H24)
1.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
1.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              82214
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.804