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_4035459
_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         'C15 H15 Br O2'
_chemical_formula_sum            'C15 H15 Br O2'
_chemical_formula_weight         307.18
_chemical_name_systematic
;
 (1S,2R,3S,5S,6R)-6-(4-bromophenyl)-2,3-dimethyl-4-oxobicyclo[3.1.0]hexane
-1-carbaldehyde
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-01-15T16:25:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.63132(6)
_cell_length_b                   12.43413(10)
_cell_length_c                   19.06466(16)
_cell_measurement_reflns_used    19232
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.379
_cell_measurement_theta_min      4.221
_cell_volume                     1334.92(2)
_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  'ShelXH-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -64.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   77.0000 -180.0000 81

  2 omega   18.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   57.0000  -30.0000 96

  3 omega  -50.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000  150.0000 45

  4 omega   42.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   30.0000 35

  5 omega   66.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 42

  6 omega   84.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 66

  7 omega   35.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 34

  8 omega   35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 31

  9 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 26

 10 omega   45.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 31

 11 omega   35.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 76

 12 omega   47.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 30

 13 omega   90.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 50

 14 omega -106.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256  -19.0000    0.0000 103

 15 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000  -90.0000 26

 16 omega   11.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000  -90.0000 38

 17 omega  -85.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  111.0000   30.0000 46

 18 omega  -61.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  -30.0000 26

 19 omega   84.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 31

 20 omega   60.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 54

 21 omega   39.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 30

 22 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 26

 23 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 26

 24 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 26

 25 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 27

 26 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 26

 27 omega   35.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -60.0000 50

 28 omega   97.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -60.0000 52

 29 omega   40.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 107

 30 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 27

 31 omega  -70.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8256   57.0000  -60.0000 103

 32 omega    7.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   77.0000   30.0000 113

 33 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   57.0000 -120.0000 104

 34 omega    2.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256 -125.0000   60.0000 96

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

 36 omega   55.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  154.0000  119.0000 62

 37 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  -30.0000 113

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

 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   30.0000 113

 41 omega -162.00  -49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 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   35.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 34

 44 omega   82.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 76

 45 omega   35.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 34

 46 omega   38.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 39

 47 omega   83.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 75

 48 omega   85.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 73

 49 omega   35.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 81

 50 omega   79.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 79

 51 omega   79.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 79

 52 omega   35.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 47

 53 omega   82.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0677437
_diffrn_orient_matrix_UB_12      -0.1182361
_diffrn_orient_matrix_UB_13      -0.0135652
_diffrn_orient_matrix_UB_21      0.0428739
_diffrn_orient_matrix_UB_22      -0.0163029
_diffrn_orient_matrix_UB_23      0.0791173
_diffrn_orient_matrix_UB_31      -0.2614542
_diffrn_orient_matrix_UB_32      -0.033295
_diffrn_orient_matrix_UB_33      0.0094647
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26470
_diffrn_reflns_theta_full        76.5
_diffrn_reflns_theta_max         76.5
_diffrn_reflns_theta_min         4.25
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.125
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.467
_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    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3033
_exptl_crystal_size_mid          0.1221
_exptl_crystal_size_min          0.0394
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0174
_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^)+(0.0250P)^2^+0.2810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0454
_reflns_number_gt                2741
_reflns_number_total             2776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00165_si_002.cif
_cod_data_source_block           a20150363_ir845b
_cod_database_code               4035459