Catalytic Enantioselective Transannular Morita-Baylis-Hillman Reaction.
Mato, Raquel; Manzano, Rubén; Reyes, Efraim; Carrillo, Luisa; Uria, Uxue; Vicario, Jose L.; Journal of the American Chemical Society 141 (2019) 9495–9499; doi:10.1021/jacs.9b03679

data_4127470
_publ_section_title
;
 Catalytic Enantioselective Transannular Morita-Baylis-Hillman Reaction.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9495
_journal_page_last               9499
_journal_paper_doi               10.1021/jacs.9b03679
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H18 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.3
_chemical_name_systematic
;
 (S)-11a-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-15T17:43:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.6489(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.33848(14)
_cell_length_b                   7.41455(12)
_cell_length_c                   9.70640(15)
_cell_measurement_reflns_used    6589
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.825
_cell_measurement_theta_min      5.983
_cell_volume                     671.799(18)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega  -56.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  -77.0000   60.0000 44

  2 omega  -60.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  -77.0000 -120.0000 26

  3 omega  -40.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  -77.0000  150.0000 30

  4 omega  -53.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  -57.0000   90.0000 38

  5 omega   16.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0756   38.0000   30.0000 41

  6 omega   14.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0756   19.0000 -180.0000 34

  7 omega  -31.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0756  -57.0000    0.0000 101

  8 omega  -76.00  -50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 26

  9 omega  -77.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -75.0000  114.1098 26

 10 omega  -81.00  -50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 31

 11 omega  -85.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000  107.8590 29

 12 omega -112.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -125.0000    0.0000 39

 13 omega  -79.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 30

 14 omega  -74.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 25

 15 omega  -94.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -67.0000   63.7881 42

 16 omega  -81.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   81.8512 25

 17 omega  -74.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 25

 18 omega -158.00 -117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -125.0000    0.0000 41

 19 omega  -85.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -52.0000  147.2217 31

 20 omega   93.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -120.0000 27

 21 omega   78.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  120.0000 26

 22 omega   79.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   90.0000 78

 23 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000 -180.0000 26

 24 omega   81.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  150.0000 39

 25 omega   77.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   60.0000 65

 26 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000   60.0000 26

 27 omega   80.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000  -60.0000 77

 28 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000 -180.0000 25

 29 omega   78.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000 -150.0000 77

 30 omega   78.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000 -120.0000 27

 31 omega   35.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000    0.0000 83

 32 omega   35.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -150.0000 33

 33 omega   86.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000  -30.0000 72

 34 omega   77.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  150.0000 25

 35 omega   45.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   60.0000 52

 36 omega  -83.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  125.0000 -150.0000 77

 37 omega   73.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0756  146.0000  -32.0000 35

 38 omega  -37.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000   30.0000 29

 39 omega   76.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000 -180.0000 32

 40 omega   28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   90.0000 26

 41 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000   90.0000 27

 42 omega   37.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000  -30.0000 62

 43 omega   42.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  -60.0000 34

 44 omega   96.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -61.0000  -90.0000 41

 45 omega -115.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0756  -57.0000  -60.0000 28

;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.138071
_diffrn_orient_matrix_UB_12      0.0109328
_diffrn_orient_matrix_UB_13      0.082625
_diffrn_orient_matrix_UB_21      -0.0904261
_diffrn_orient_matrix_UB_22      -0.0114658
_diffrn_orient_matrix_UB_23      -0.135039
_diffrn_orient_matrix_UB_31      -0.0021456
_diffrn_orient_matrix_UB_32      -0.2071887
_diffrn_orient_matrix_UB_33      0.0117808
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6922
_diffrn_reflns_theta_full        66.48
_diffrn_reflns_theta_max         66.48
_diffrn_reflns_theta_min         6.49
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.5757
_exptl_crystal_size_mid          0.2967
_exptl_crystal_size_min          0.2109
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0244
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.0950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                2239
_reflns_number_total             2251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9b03679_si_002.cif
_cod_data_source_block           a20160444_rm597a
_cod_database_code               4127470