Asymmetric Synthesis of Tri- and Tetrasubstituted Trifluoromethyl Dihydropyranones from α-Aroyloxyaldehydes via NHC Redox Catalysis
Davies, Alyn T.; Pickett, Philip M.; Slawin, Alexandra M. Z.; Smith, Andrew D.; ACS Catalysis 4 (2014) 2696–; doi:10.1021/cs500667g

data_4511644
_publ_section_title
;
 Asymmetric Synthesis of Tri- and Tetrasubstituted Trifluoromethyl
 Dihydropyranones from \a-Aroyloxyaldehydes via NHC Redox Catalysis
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              2696
_journal_paper_doi               10.1021/cs500667g
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H12 Br F3 O2'
_chemical_formula_sum            'C14 H12 Br F3 O2'
_chemical_formula_weight         349.15
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.041(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.1604(15)
_cell_length_b                   9.5399(18)
_cell_length_c                   9.6845(18)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      3.09
_cell_volume                     712.7(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 7.353
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4520
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         3.084
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.923
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             348.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.330
_refine_ls_abs_structure_details
'Parsons and Flack (2004), Acta Cryst. A60, s61.  757 quotients'
_refine_ls_abs_structure_Flack   0.026(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                2058
_reflns_number_total             2348
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs500667g_si_003.cif
_cod_data_source_block           19
_cod_depositor_comments
'Adding full bibliography for 4511643--4511645.cif.'
_cod_original_cell_volume        712.7(3)
_cod_database_code               4511644