Stereoselective Construction of Cyclic Ethers Using a Tandem Two-Component Etherification: Elucidation of the Role of Bismuth Tribromide
P. Andrew Evans; Jian Cui; Santosh J. Gharpure; Robert J. Hinkle; Journal of the American Chemical Society 125 (2003) 11456–11457; doi:10.1021/ja036439j

data_4114197
_publ_contact_author_address
;
        Indiana University
        Department of Chemistry
        800 E. Kirkwood Ave.
        Bloomington, IN 47405-7102
        USA
;
_publ_contact_author_email       paevans@indiana.edu
_publ_contact_author_fax         '++ 812 855 8300'
_publ_contact_author_name        'Evans, P. Andrew'
_publ_contact_author_phone       '++ 812 855 7368'
_publ_section_title
;
 Stereoselective Construction of Cyclic Ethers Using a Tandem
 Two-Component Etherification: Elucidation of the Role of Bismuth
 Tribromide
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11456
_journal_page_last               11457
_journal_paper_doi               10.1021/ja036439j
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.563(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9308(18)
_cell_length_b                   7.6574(19)
_cell_length_c                   33.874(9)
_cell_measurement_reflns_used    973
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.41
_cell_volume                     1796.0(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999), XTEL (local)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
'   0.30 degree frames measured for 5 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       '\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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            38263
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0234P)^2^+2.6253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                3504
_reflns_number_total             4130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036439jsi20030705_013817.cif
_cod_data_source_block           03091
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4114197