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_7127336
_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         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_systematic
;
 (2S,2aS,2a1S,5aR)-5a-hydroxy-2-(methoxycarbonyl)-2a,2a1,3,4,5,5a,6,7-
octahydro-2H-benzo[6,7]cyclohepta[1,2,3-cd]isoindole 1-oxide
;
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-06-19T16:04:51-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.19139(11)
_cell_length_b                   11.21187(14)
_cell_length_c                   15.13619(18)
_cell_measurement_reflns_used    9239
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.13
_cell_measurement_theta_min      5.594
_cell_volume                     1559.82(3)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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   -131.00  37.00   1.00    1.00    --  -42.38   0.00-120.00  168
  2  \w     83.00 108.00   1.00    1.00    --   42.38 166.00-163.00   25
  3  \w     37.00  63.00   1.00    3.00    --  107.93 -30.00 150.00   26
  4  \w     35.00  69.00   1.00    3.00    --  107.93 -30.00  60.00   34
  5  \w     33.00  66.00   1.00    3.00    --  107.93 -30.00-150.00   33
  6  \w     82.00 156.00   1.00    3.00    --  107.93  61.00   0.00   74
  7  \w     33.00 103.00   1.00    3.00    --  107.93 -94.00 150.00   70
  8  \w     34.00  67.00   1.00    3.00    --  107.93 -30.00-180.00   33
  9  \w     43.00  92.00   1.00    3.00    --  107.93-125.00 120.00   49
 10  \w     79.00 153.00   1.00    3.00    --  107.93  77.00-120.00   74
 11  \w    -89.00 -15.00   1.00    1.00    --  -42.38 -51.00-168.00   74
 12  \w    -98.00 -33.00   1.00    1.00    --  -42.38 125.00 -60.00   65
 13  \w     34.00  70.00   1.00    1.00    --   42.38-125.00-180.00   36
 14  \w      4.00  36.00   1.00    1.00    --   42.38-125.00 120.00   32
 15  \w     41.00  67.00   1.00    3.00    --  107.93 -30.00   0.00   26
 16  \w     81.00 118.00   1.00    3.00    --  107.93  30.00 -30.00   37
 17  \w     36.00  62.00   1.00    3.00    --  107.93 -30.00  90.00   26
 18  \w     39.00  65.00   1.00    3.00    --  107.93 -30.00 -90.00   26
 19  \w     35.00  63.00   1.00    3.00    --  107.93 -30.00 120.00   28
 20  \w     47.00  81.00   1.00    3.00    --  107.93 -94.00  30.00   34
 21  \w     53.00  79.00   1.00    3.00    --  107.93 -61.00  60.00   26
 22  \w    104.00 132.00   1.00    3.00    --  107.93 -61.00  60.00   28
 23  \w     42.00 141.00   1.00    3.00    --  107.93 -77.00-150.00   99
 24  \w    129.00 155.00   1.00    3.00    --  107.93  30.00 -30.00   26
 25  \w     90.00 116.00   1.00    3.00    --  107.93-125.00 120.00   26
 26  \w     79.00 113.00   1.00    3.00    --  107.93-125.00 -90.00   34
 27  \w     87.00 130.00   1.00    3.00    --  107.93  61.00  60.00   43
 28  \w     36.00  69.00   1.00    3.00    --  107.93 -30.00 -30.00   33
 29  \w     83.00 110.00   1.00    3.00    --  107.93 -94.00 -60.00   27
 30  \w    -67.00  32.00   1.00    1.00    --  -42.38  38.00  30.00   99
 31  \w   -116.00 -14.00   1.00    1.00    --  -42.38 -57.00  90.00  102
 32  \w   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00-150.00  109
 33  \w   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00 -60.00  109
 34  \w      2.00  71.00   1.00    1.00    --   42.38-125.00 -90.00   69
;
_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      0.0295173
_diffrn_orient_matrix_UB_12      0.1350103
_diffrn_orient_matrix_UB_13      0.0063193
_diffrn_orient_matrix_UB_21      -0.1299989
_diffrn_orient_matrix_UB_22      0.0136756
_diffrn_orient_matrix_UB_23      0.0634675
_diffrn_orient_matrix_UB_31      0.1015605
_diffrn_orient_matrix_UB_32      -0.0217064
_diffrn_orient_matrix_UB_33      0.0793131
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16448
_diffrn_reflns_theta_full        74.42
_diffrn_reflns_theta_max         74.42
_diffrn_reflns_theta_min         4.91
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.82285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(16)
_refine_ls_extinction_coef       0.0009(3)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.1329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                2946
_reflns_number_total             3134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc05981a2.cif
_cod_data_source_block           a20180380_rm998f1
_cod_depositor_comments
'Adding full bibliography for 7127335--7127336.cif.'
_cod_database_code               7127336