A Critical Analysis of the Mechanistic Basis of Enantioselectivity in the Bis-Cinchona Alkaloid Catalyzed Dihydroxylation of Olefins
E. J. Corey; Mark C. Noe; Journal of the American Chemical Society 118 (1996) 11038–11053; doi:10.1021/ja961233m

data_4117207
_publ_section_title
;
 A Critical Analysis of the Mechanistic Basis of Enantioselectivity in the
 Bis-Cinchona Alkaloid Catalyzed Dihydroxylation of Olefins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11038
_journal_page_last               11053
_journal_paper_doi               10.1021/ja961233m
_journal_volume                  118
_journal_year                    1996
_chemical_formula_sum            'C23 H17 Br O3'
_chemical_formula_weight         421.28
_chemical_name_common
;
4-Bromobenzoate of Asymmetric Dihydroxylation Product from 
Dihydro-fluroanthene
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.233(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3839(11)
_cell_length_b                   12.1229(14)
_cell_length_c                   18.411(2)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1870.8(4)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'Siemens Xcif'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'Omega 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  0.0573
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10029
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        <5%
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.218
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.007
_refine_ls_goodness_of_fit_obs   1.066
_refine_ls_hydrogen_treatment    'Riding Model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_restrained_S_obs      1.066
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_obs          0.0555
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1319
_refine_ls_wR_factor_obs         0.1078
_reflns_number_observed          4090
_reflns_number_total             6529
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja961233m_3.cif
_cod_data_source_block           tricycle
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4117207