Catalytic enantioselective domino Michael/transannular aldol reaction under bifunctional catalysis.
Mato, Raquel; Reyes, Efraim; Carrillo, Luisa; Uria, Uxue; Prieto, Liher; Manzano, Ruben; Vicario, Jose L.; Chemical communications (Cambridge, England) 56 (2020) 13149–13152; doi:10.1039/d0cc05981a

data_7127335
_publ_section_title
;
 Catalytic enantioselective domino Michael/transannular aldol reaction
 under bifunctional catalysis.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13149
_journal_page_last               13152
_journal_paper_doi               10.1039/d0cc05981a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H18 Br N O4'
_chemical_formula_sum            'C16 H18 Br N O4'
_chemical_formula_weight         368.22
_chemical_name_systematic
(4S,4aR,11aR)-7-bromo-11a-hydroxy-4-(nitromethyl)-1,2,3,4,4a,10,11,11a-octahydro-5H-dibenzo[a,d][7]annulen-5-one
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-06-19T16:02:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-06-19 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5299(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.42782(17)
_cell_length_b                   7.69850(11)
_cell_length_c                   11.51764(17)
_cell_measurement_reflns_used    11475
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.678
_cell_measurement_theta_min      3.991
_cell_volume                     886.41(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_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   -113.00 -15.00   1.00    1.00    --  -41.88 -57.00  30.00   98
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.88 -38.00 -90.00   99
  3  \w    -83.00 -18.00   1.00    1.00    --  -41.88 -38.00  90.00   65
  4  \w      6.00  66.00   1.00    1.00    --   41.88-125.00  90.00   60
  5  \w      4.00  51.00   1.00    1.00    --   41.88-125.00 -90.00   47
  6  \w     43.00  70.00   1.00    1.00    --  109.18-125.00   0.00   27
  7  \w     34.00  69.00   1.00    1.00    --  109.18 -30.00  30.00   35
  8  \w     38.00 143.00   1.00    1.00    --  109.18 -83.00  17.00  105
  9  \w     87.00 158.00   1.00    1.00    --  109.18  61.00 -90.00   71
 10  \w    128.00 155.00   1.00    1.00    --  109.18  45.00  60.00   27
 11  \w     36.00  61.00   1.00    1.00    --  109.18 -45.00   0.00   25
 12  \w     45.00 117.00   1.00    1.00    --  109.18-125.00-150.00   72
 13  \w     33.00  62.00   1.00    1.00    --  109.18 -30.00 -30.00   29
 14  \w     36.00  64.00   1.00    1.00    --  109.18 -45.00 -60.00   28
 15  \w     84.00 111.00   1.00    1.00    --  109.18  45.00  60.00   27
 16  \w     61.00 145.00   1.00    1.00    --  109.18  15.00 -90.00   84
 17  \w     33.00  61.00   1.00    1.00    --  109.18 -30.00-150.00   28
 18  \w     78.00 155.00   1.00    1.00    --  109.18  77.00 150.00   77
 19  \w     84.00 114.00   1.00    1.00    --  109.18-125.00   0.00   30
 20  \w     76.00 135.00   1.00    1.00    --  109.18 -15.00-180.00   59
 21  \w     39.00  66.00   1.00    1.00    --  109.18 -30.00   0.00   27
 22  \w     30.00  57.00   1.00    1.00    --  109.18 -15.00-180.00   27
 23  \w    -50.00 -18.00   1.00    1.00    --  -41.88 -57.00 120.00   32
 24  \w     41.00  93.00   1.00    1.00    --   41.88-125.00 -60.00   52
 25  \w     39.00  69.00   1.00    1.00    --  109.18 -45.00 150.00   30
 26  \w     41.00  82.00   1.00    1.00    --  109.18 -94.00 -60.00   41
 27  \w     33.00  62.00   1.00    1.00    --  109.18 -30.00  90.00   29
 28  \w     68.00 116.00   1.00    1.00    --  109.18-125.00  30.00   48
 29  \w     49.00  76.00   1.00    1.00    --  109.18 -45.00  30.00   27
 30  \w     36.00  61.00   1.00    1.00    --  109.18 -45.00-150.00   25
 31  \w     36.00  86.00   1.00    1.00    --  109.18 -94.00-120.00   50
 32  \w   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00-150.00  100
 33  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00 150.00  109
 34  \w    -98.00  -2.00   1.00    1.00    --  -41.88 125.00 120.00   96
 35  \w    -30.00  70.00   1.00    1.00    --   41.88 -57.00 -90.00  100
 36  \w      9.00 118.00   1.00    1.00    --   41.88  77.00   0.00  109
 37  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00-120.00  109
 38  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00  30.00  109
 39  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00-180.00  109
 40  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00 -60.00  109
 41  \w    -66.00  32.00   1.00    1.00    --  -41.88  38.00-180.00   98
 42  \w   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00  60.00  100
 43  \w   -118.00  -9.00   1.00    1.00    --  -41.88 -77.00  60.00  109
 44  \w   -116.00 -17.00   1.00    1.00    --  -41.88 -38.00  60.00   99
 45  \w   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00 -30.00  100
 46  \w   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00  30.00  100
 47  \w   -122.00  -1.00   1.00    1.00    --  -41.88 -19.00 -30.00  121
 48  \w   -114.00 -14.00   1.00    1.00    --  -41.88 -57.00   0.00  100
 49  \w    -46.00 130.00   1.00    1.00    --   41.88   0.00-180.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1483667
_diffrn_orient_matrix_UB_12      0.038815
_diffrn_orient_matrix_UB_13      -0.0632953
_diffrn_orient_matrix_UB_21      0.0400323
_diffrn_orient_matrix_UB_22      0.1707609
_diffrn_orient_matrix_UB_23      -0.0501965
_diffrn_orient_matrix_UB_31      0.0111281
_diffrn_orient_matrix_UB_32      -0.0968558
_diffrn_orient_matrix_UB_33      -0.113781
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16349
_diffrn_reflns_theta_full        74.77
_diffrn_reflns_theta_max         74.77
_diffrn_reflns_theta_min         4
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.303
_exptl_absorpt_correction_T_max  0.781
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.651
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.847
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.193
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0109(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1314P)^2^+0.3789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.185
_refine_ls_wR_factor_ref         0.1885
_reflns_number_gt                3346
_reflns_number_total             3542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc05981a2.cif
_cod_data_source_block           a20190047_rm1098rem
_cod_depositor_comments
'Adding full bibliography for 7127335--7127336.cif.'
_cod_database_code               7127335