H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins
Ding, Pei-Gang; Zhou, Feng; Wang, Xin; Zhao, Qiu-Hua; Yu, Jin-Sheng; Zhou, Jian; Chemical Science 11 (2020) 3852–3861; doi:10.1039/D0SC00475H

data_1557582
_publ_section_title
;
 H-bond donor-directed switching of diastereoselectivity in the Michael
 addition of \a-azido ketones to nitroolefins
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              3852
_journal_page_last               3861
_journal_paper_doi               10.1039/D0SC00475H
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H14 Br2 N4 O3'
_chemical_formula_sum            'C18 H14 Br2 N4 O3'
_chemical_formula_weight         494.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.259(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.63640(10)
_cell_length_b                   11.6851(2)
_cell_length_c                   11.5473(2)
_cell_measurement_reflns_used    12619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9920
_cell_measurement_theta_min      5.4150
_cell_volume                     998.65(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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    -40.00 -14.00   1.00    2.00    --    0.00 -52.00 -80.00   26
  2  \w    -22.00  45.00   1.00    2.00    --    0.00  52.00  65.00   67
  3  \w     42.00  67.00   1.00    2.00    --   95.80 -52.00 -80.00   25
  4  \w     76.00 172.00   1.00    2.00    --   95.80  52.00  65.00   96
  5  \w    -21.00  23.00   1.00    2.00    --    0.00 -57.00  60.00   44
  6  \w     39.00  84.00   1.00    2.00    --    0.00  38.00   0.00   45
  7  \w    -19.00  33.00   1.00    2.00    --    0.00  38.00   0.00   52
  8  \w      7.00  62.00   1.00    2.00    --    0.00  77.00  60.00   55
  9  \w    -89.00 -51.00   1.00    2.00    --    0.00 -38.00 -60.00   38
 10  \w    -89.00 -30.00   1.00    2.00    --    0.00 -57.00  60.00   59
 11  \w    -11.00  24.00   1.00    2.00    --    0.00 -19.00-150.00   35
 12  \w    -43.00  17.00   1.00    2.00    --    0.00 -38.00 -60.00   60
 13  \w    -22.00  54.00   1.00    2.00    --    0.00  57.00 -60.00   76
 14  \w     39.00  75.00   1.00    2.00    --    0.00  19.00-120.00   36
 15  \w    -19.00  31.00   1.00    2.00    --    0.00  38.00 150.00   50
 16  \w    -50.00 -24.00   1.00    2.00    --    0.00 -19.00-150.00   26
 17  \w    -19.00  33.00   1.00    2.00    --    0.00  19.00-120.00   52
 18  \w     65.00 118.00   1.00    2.00    --   95.80  79.00 161.77   53
 19  \w     72.00 107.00   1.00    2.00    --   95.80  58.00  41.77   35
 20  \w     41.00 126.00   1.00    2.00    --   95.80 -82.00 150.00   85
 21  \w     73.00 128.00   1.00    2.00    --   95.80 -82.00 -60.00   55
 22  \w     79.00 128.00   1.00    2.00    --   95.80 -82.00-150.00   49
 23  \w     11.00  37.00   1.00    2.00    --   95.80 -82.00 150.00   26
 24  \w    145.00 172.00   1.00    2.00    --   95.80  77.00-150.00   27
 25  \w    129.00 159.00   1.00    2.00    --   95.80  45.00  30.00   30
 26  \w    114.00 173.00   1.00    2.00    --   95.80  79.00 -77.07   59
 27  \w     75.00 119.00   1.00    2.00    --   95.80  45.00  30.00   44
 28  \w     71.00  96.00   1.00    2.00    --   95.80  61.00-150.00   25
 29  \w     65.00  99.00   1.00    2.00    --   95.80  77.00 120.00   34
 30  \w     75.00 114.00   1.00    2.00    --   95.80  45.00   0.00   39
 31  \w    116.00 141.00   1.00    2.00    --   95.80  45.00   0.00   25
 32  \w    149.00 185.00   1.00    2.00    --   95.80  45.00   0.00   36
 33  \w     64.00  89.00   1.00    2.00    --   95.80  80.00 100.76   25
 34  \w     67.00  93.00   1.00    2.00    --   95.80  73.00  78.89   26
 35  \w     75.00 121.00   1.00    2.00    --   95.80  45.00 -90.00   46
 36  \w     65.00 178.00   1.00    2.00    --   95.80  77.00  90.00  113
 37  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 38  \w    146.00 171.00   1.00    2.00    --   95.80  77.00   0.00   25
 39  \w     75.00 185.00   1.00    2.00    --   95.80  45.00 -30.00  110
 40  \w     63.00 185.00   1.00    2.00    --   95.80  82.00 130.09  122
 41  \w     80.00 184.00   1.00    2.00    --   95.80  45.00-120.00  104
 42  \w    111.00 156.00   1.00    2.00    --   95.80  82.00 150.00   45
 43  \w     71.00 175.00   1.00    2.00    --   95.80  59.00  76.40  104
 44  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 45  \w    152.00 178.00   1.00    2.00    --   95.80  77.00  60.00   26
 46  \w     64.00  98.00   1.00    2.00    --   95.80  79.00 -77.07   34
 47  \w    116.00 185.00   1.00    2.00    --   95.80  82.00-120.00   69
 48  \w     69.00  95.00   1.00    2.00    --   95.80  82.00 -30.00   26
 49  \w    139.00 168.00   1.00    2.00    --   95.80  82.00 -30.00   29
 50  \w     64.00  89.00   1.00    2.00    --   95.80  82.00   0.00   25
 51  \w     63.00  99.00   1.00    2.00    --   95.80  82.00 150.00   36
 52  \w     68.00 123.00   1.00    2.00    --   95.80 -77.00 -90.00   55
 53  \w     12.00  49.00   1.00    2.00    --   95.80 -77.00 -90.00   37
 54  \w     65.00  91.00   1.00    2.00    --   95.80  77.00  30.00   26
 55  \w     76.00 102.00   1.00    2.00    --   95.80  61.00  60.00   26
 56  \w     66.00  92.00   1.00    2.00    --   95.80  77.00 -90.00   26
 57  \w     63.00  88.00   1.00    2.00    --   95.80  82.00 120.00   25
 58  \w     78.00 122.00   1.00    2.00    --   95.80 -82.00   0.00   44
 59  \w     71.00  96.00   1.00    2.00    --   95.80  61.00-120.00   25
 60  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 61  \w    139.00 169.00   1.00    2.00    --   95.80  77.00-180.00   30
 62  \w     61.00 105.00   1.00    2.00    --   95.80 -82.00  90.00   44
 63  \w    130.00 167.00   1.00    2.00    --   95.80  79.00 161.77   37
 64  \w     89.00 115.00   1.00    2.00    --   95.80  30.00 -60.00   26
 65  \w     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 66  \w     65.00  91.00   1.00    2.00    --   95.80  77.00   0.00   26
 67  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 68  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1207180000
_diffrn_orient_matrix_UB_12      0.0873431000
_diffrn_orient_matrix_UB_13      0.0436225000
_diffrn_orient_matrix_UB_21      -0.1357054000
_diffrn_orient_matrix_UB_22      -0.0037369000
_diffrn_orient_matrix_UB_23      -0.1231976000
_diffrn_orient_matrix_UB_31      -0.1017326000
_diffrn_orient_matrix_UB_32      -0.0986824000
_diffrn_orient_matrix_UB_33      0.0431811000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21816
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.458
_diffrn_reflns_theta_min         3.950
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017) 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    1.643
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(12)
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0605P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3735
_reflns_number_total             4011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc00475h3.cif
_cod_data_source_block           exp_517
_cod_depositor_comments
;Adding full bibliography for 1557580--1557584.cif.

 Adding full bibliography for 1557580--1557584.cif.
;
_cod_database_code               1557582
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.445
_shelx_estimated_absorpt_t_min   0.278
_reflns_odcompleteness_completeness 100.00
_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 C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
;
_shelx_res_checksum              13800
_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 4.897
_oxdiff_exptl_absorpt_empirical_full_min 0.287