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_4117206
_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            'C20 H15 Br O2'
_chemical_formula_weight         367.23
_chemical_name_common            'Dihydroxylation product of 14-Bromo 7'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   14.597(2)
_cell_length_b                   20.560(7)
_cell_length_c                   22.004(3)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     6604(3)
_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      293(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  0.0980
_diffrn_reflns_av_sigmaI/netI    0.1198
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_theta_max         20.00
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        <5%
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.497
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       Prisms
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    'Riding Model'
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_refine_ls_number_restraints     0
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_refine_ls_restrained_S_obs      1.093
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_obs          0.0968
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1568P)^2^+11.2578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2688
_refine_ls_wR_factor_obs         0.2248
_reflns_number_observed          3790
_reflns_number_total             6044
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja961233m_2.cif
_cod_data_source_block           brfluore
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1568P)^2^+11.2578P] 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^)+(0.1568P)^2^+11.2578P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        6603.7(26)
_cod_database_code               4117206