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_4511645
_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         'C13 H14 Br F3 O2'
_chemical_formula_sum            'C13 H14 Br F3 O2'
_chemical_formula_weight         339.15
_space_group_IT_number           19
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.0430(7)
_cell_length_b                   7.8416(9)
_cell_length_c                   29.273(4)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.34
_cell_volume                     1387.2(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r2'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1098
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.333
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.620
_refine_ls_abs_structure_details
'Parsons and Flack (2004), Acta Cryst. A60, s61. 624 quotients'
_refine_ls_abs_structure_Flack   0.018(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                2084
_reflns_number_total             3151
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs500667g_si_004.cif
_cod_data_source_block           28
_cod_depositor_comments
'Adding full bibliography for 4511643--4511645.cif.'
_cod_database_code               4511645