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_4127471
_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         'C11 H16 O2'
_chemical_formula_sum            'C11 H16 O2'
_chemical_formula_weight         180.24
_chemical_name_systematic
;
 (R,Z)-7-methylcyclodec-2-ene-1,6-dione
;
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-20T11:40:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.2082(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.36038(10)
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_cell_length_c                   12.53807(18)
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_cell_measurement_temperature    150.00(10)
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_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
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_diffrn_measured_fraction_theta_max 0.972
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;
  1 omega -122.00  -95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -99.0000 -180.0000 27

  2 omega  -65.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256   38.0000  150.0000 96

  3 omega  -59.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256   57.0000 -150.0000 81

  4 omega -124.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -99.0000 -120.0000 40

  5 omega  -14.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3256  -99.0000  -60.0000 95

  6 omega  -68.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000   90.0000 48

  7 omega   81.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000 -180.0000 73

  8 omega   78.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000  -60.0000 78

  9 omega   97.00  146.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  125.0000 -120.0000 49

 10 omega   30.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   90.0000 33

 11 omega   64.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -77.0000   90.0000 76

 12 omega   85.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -135.0000  -41.0000 41

 13 omega   30.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -94.0000  -30.0000 76

 14 omega   36.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000    0.0000 29

 15 omega   71.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -125.0000   90.0000 51

 16 omega  117.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   90.0000 28

 17 omega   77.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   90.0000 34

 18 omega   42.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609 -135.0000  -41.0000 42

 19 omega   33.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  120.0000 27

 20 omega   81.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   61.0000 -120.0000 70

 21 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000  120.0000 25

 22 omega -117.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -99.0000  -60.0000 30

 23 omega   79.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3256   38.0000 -180.0000 29

 24 omega   32.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -90.0000 27

 25 omega  123.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   30.0000 27

 26 omega   91.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   30.0000 27

 27 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  150.0000 25

 28 omega   31.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000  -60.0000 36

 29 omega   80.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   60.0000 27

 30 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -57.0000 -180.0000 103

 31 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -57.0000   60.0000 103

 32 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -99.0000  120.0000 45

 33 omega -120.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -77.0000   30.0000 112

 34 omega -120.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -77.0000 -180.0000 112

 35 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -57.0000  -60.0000 103

 36 omega -120.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -77.0000  -90.0000 112

 37 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3256  -57.0000   30.0000 103

 38 omega -162.00 -115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 47

 39 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -90.0000 113

 40 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 113

 41 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

 42 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

 43 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000    0.0000 113

 44 omega   81.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000   90.0000 77

 45 omega   75.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000  120.0000 83

 46 omega   81.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   45.0000    0.0000 77

 47 omega   30.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -30.0000    0.0000 39

 48 omega   75.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609   77.0000   30.0000 83

 49 omega   34.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3609  -45.0000 -180.0000 43

;
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_theta_max         74.24
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_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.095
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_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         1932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0307
_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^)+(0.0438P)^2^+0.0668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1904
_reflns_number_total             1932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9b03679_si_004.cif
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