Organocatalytic Transannular Approach to Stereodefined Bicyclo[3.1.0]hexanes.
Riaño, Iker; Uria, Uxue; Reyes, Efraím; Carrillo, Luisa; Vicario, Jose L.; The Journal of organic chemistry 83 (2018) 4180–4189; doi:10.1021/acs.joc.8b00165

data_4035458
_publ_section_title
;
 Organocatalytic Transannular Approach to Stereodefined
 Bicyclo[3.1.0]hexanes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4180
_journal_page_last               4189
_journal_paper_doi               10.1021/acs.joc.8b00165
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H20 O5'
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_chemical_name_systematic
;
 4-((1S,2S,3S,5S,6R)-1-formyl-2,3-dimethyl-4-oxobicyclo[3.1.0]hexan-6-yl)
-2-methoxyphenyl acetate
;
_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             2018-01-16T17:29:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.880(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7133(2)
_cell_length_b                   7.17114(15)
_cell_length_c                   15.5989(4)
_cell_measurement_reflns_used    8075
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      76.217
_cell_measurement_theta_min      2.878
_cell_volume                     837.63(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_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      294.0(10)
_diffrn_detector_area_resol_mean 10.4023
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -93.00  -28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  125.0000 -120.0000 65

  2 omega -123.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256    0.0000   30.0000 169

  3 omega   35.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   37.0000   60.0000 35

  4 omega  -67.00  -16.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  -90.0000 51

  5 omega  -59.00  -33.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  120.0000 26

  6 omega -123.00  -54.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000    0.0000 69

  7 omega   35.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 33

  8 omega   93.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 51

  9 omega   80.00  142.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 62

 10 omega  127.00  153.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 11 omega   40.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 26

 12 omega   35.00   60.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 25

 13 omega   43.00  100.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -59.0000  136.0000 57

 14 omega  111.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 35

 15 omega   34.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  120.0000 75

 16 omega   47.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 26

 17 omega   84.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 60

 18 omega   79.00  155.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -180.0000 76

 19 omega   38.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 26

 20 omega   80.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 27

 21 omega   45.00   74.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 29

 22 omega  117.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 37

 23 omega   36.00   66.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 30

 24 omega   40.00   65.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 25

 25 omega   86.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 60

 26 omega   47.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 26

 27 omega  -27.00   -1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   77.0000   60.0000 26

 28 omega  -62.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   77.0000   60.0000 29

 29 omega -160.00 -120.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -111.0000    0.0000 40

 30 omega   76.00  102.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 26

 31 omega   42.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 31

 32 omega   57.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 51

 33 omega   30.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 73

 34 omega   93.00  139.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 46

 35 omega   63.00  103.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -90.0000 40

 36 omega  -98.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  125.0000   90.0000 96

 37 omega  -74.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   77.0000   30.0000 112

 38 omega    7.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000   60.0000 113

 39 omega    7.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000  150.0000 113

 40 omega   11.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   57.0000  -90.0000 104

 41 omega    7.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000  -60.0000 113

 42 omega -162.00 -126.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 36

 43 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 113

 44 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 113

 45 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -60.0000 113

 46 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 113

 47 omega -162.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 113

 48 omega -157.00  -53.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -61.0000 -180.0000 104

 49 omega   35.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 81

 50 omega   85.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 73

 51 omega   83.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 75

 52 omega   35.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 34

 53 omega   82.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1430348
_diffrn_orient_matrix_UB_12      0.1390123
_diffrn_orient_matrix_UB_13      0.0478562
_diffrn_orient_matrix_UB_21      0.023196
_diffrn_orient_matrix_UB_22      0.0711843
_diffrn_orient_matrix_UB_23      -0.089796
_diffrn_orient_matrix_UB_31      -0.1459126
_diffrn_orient_matrix_UB_32      0.1475173
_diffrn_orient_matrix_UB_33      -0.0017115
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16079
_diffrn_reflns_theta_full        76.68
_diffrn_reflns_theta_max         76.68
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
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    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.7221
_exptl_crystal_size_mid          0.464
_exptl_crystal_size_min          0.0575
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.129
_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   -0.18(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.038
_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^)+(0.0670P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                3207
_reflns_number_total             3434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00165_si_003.cif
_cod_data_source_block           a20150419_ir853c_sncuta
_cod_database_code               4035458