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_4511643
_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 H10 Br F3 O2'
_chemical_formula_sum            'C13 H10 Br F3 O2'
_chemical_formula_weight         335.12
_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                   6.384(3)
_cell_length_b                   11.747(5)
_cell_length_c                   17.072(7)
_cell_measurement_reflns_used    3712
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.95
_cell_volume                     1280.3(10)
_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      93
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7788
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         2.105
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.251
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.580
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  947 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.004(21)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1719
_reflns_number_total             2316
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs500667g_si_002.cif
_cod_data_source_block           14
_cod_depositor_comments
'Adding full bibliography for 4511643--4511645.cif.'
_cod_original_cell_volume        1280.3(9)
_cod_database_code               4511643