Origins of Stereoselectivities of Dihydroxylations of cis-Bicyclo[3.3.0]octenes
Hao Wang; Philipp Kohler; Larry E. Overman; K. N. Houk; Journal of the American Chemical Society 134 (2012) 16054–16058; doi:10.1021/ja3075538

data_4118701
_publ_section_title
;
 Origins of Stereoselectivities of Dihydroxylations of
 cis-Bicyclo[3.3.0]octenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16054
_journal_page_last               16058
_journal_paper_doi               10.1021/ja3075538
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C13 H20 O7'
_chemical_formula_weight         288.29
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_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   33.1098(13)
_cell_length_b                   33.1098(13)
_cell_length_c                   6.3799(3)
_cell_measurement_reflns_used    8496
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.46
_cell_volume                     6057.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
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_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23307
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9678
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_description       hexagon
_exptl_crystal_F_000             2772
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.197
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     261
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+7.9802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2622
_reflns_number_total             2968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3075538_si_003.cif
_cod_data_source_block           leo242
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4118701