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_4118700
_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            'C19 H22 O5'
_chemical_formula_weight         330.37
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_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.9275(2)
_cell_length_b                   22.3693(8)
_cell_length_c                   25.6873(9)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.41
_cell_volume                     3406.0(2)
_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      93(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
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_diffrn_reflns_limit_h_max       8
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_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
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_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            38193
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.89
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.347
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_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+1.2455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                3623
_reflns_number_total             4309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3075538_si_002.cif
_cod_data_source_block           leo239
_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_database_code               4118700