Desymmetrization of gem-diols via water-assisted organocatalytic enantio- and diastereoselective cycloetherification.
Murata, Ryuichi; Matsumoto, Akira; Asano, Keisuke; Matsubara, Seijiro; Chemical communications (Cambridge, England) 56 (2020) 12335–12338; doi:10.1039/d0cc05509c

data_7127142
_publ_section_title
;
 Desymmetrization of gem-diols via water-assisted organocatalytic enantio-
 and diastereoselective cycloetherification.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12335
_journal_page_last               12338
_journal_paper_doi               10.1039/d0cc05509c
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H14 Br F3 O3'
_chemical_formula_sum            'C14 H14 Br F3 O3'
_chemical_formula_weight         367.16
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_update_record
;
2020-08-07 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
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_cell_length_b                   17.8856(12)
_cell_length_c                   21.2028(14)
_cell_measurement_reflns_used    21629
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      3.10
_cell_volume                     3102.5(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30843
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.695
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_exptl_absorpt_correction_T_min  0.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472.00
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.450
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_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3110 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.019(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     379
_refine_ls_number_reflns         7116
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0333P)^2^+1.8274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                3945
_reflns_number_total             7116
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d0cc05509c2.cif
_cod_data_source_block           2019_02_19_2
_cod_depositor_comments
'Adding full bibliography for 7127142--7127143.cif.'
_cod_original_cell_volume        3102.5(4)
_cod_database_code               7127142