Catalyst-controlled diastereoselectivity reversal in the formation of dihydropyrans.
Kano, Taichi; Maruyama, Hiroki; Homma, Chihiro; Maruoka, Keiji; Chemical communications (Cambridge, England) 54 (2018) 3496–3499; doi:10.1039/C8CC01443D

data_7121400
_publ_section_title
;
 Catalyst-controlled diastereoselectivity reversal in the formation of
 dihydropyrans.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3496
_journal_page_last               3499
_journal_paper_doi               10.1039/C8CC01443D
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H20 Br F3 O4'
_chemical_formula_sum            'C23 H20 Br F3 O4'
_chemical_formula_weight         497.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_update_record
;
2017-11-15 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.3578(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
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_cell_length_b                   5.81849(17)
_cell_length_c                   15.3547(4)
_cell_measurement_reflns_used    9272
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      2.97
_cell_volume                     1092.17(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9822
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         2.971
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.041
_exptl_absorpt_correction_T_max  0.738
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504.00
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
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_refine_diff_density_max         0.87
_refine_diff_density_min         -0.30
_refine_ls_abs_structure_details
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.036(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.775
_reflns_Friedel_fraction_max     0.772
_reflns_number_gt                3268
_reflns_number_total             3559
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8cc01443d2.cif
_cod_data_source_block           7X11
_cod_depositor_comments          'Adding full bibliography for 7121400.cif.'
_cod_original_cell_volume        1092.17(5)
_cod_database_code               7121400
_shelx_res_checksum              36933