Highly Enantioselective Organocatalytic Trifluoromethyl Carbinol Synthesis-A Caveat on Reaction Times and Product Isolation
Nongnaphat Duangdee; Wacharee Harnying; Giuseppe Rulli; Jörg-M. Neudörfl; Harald Gröger; Albrecht Berkessel; Journal of the American Chemical Society 134 (2012) 11196–11205; doi:10.1021/ja302511t

data_4118217
_publ_section_title
;
 Highly Enantioselective Organocatalytic Trifluoromethyl Carbinol
 Synthesis-A Caveat on Reaction Times and Product Isolation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11196
_journal_page_last               11205
_journal_paper_doi               10.1021/ja302511t
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H10 Cl F3 O2'
_chemical_formula_sum            'C11 H10 Cl F3 O2'
_chemical_formula_weight         266.64
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.2509(6)
_cell_length_b                   15.2491(15)
_cell_length_c                   15.8315(15)
_cell_measurement_reflns_used    11033
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.85
_cell_volume                     2233.3(3)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.1059
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11033
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .02
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3009
_reflns_number_total             4659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja302511t_si_003.cif
_cod_data_source_block           nod368
_cod_database_code               4118217