Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture
Fedor Romanov-Michailidis; Marion Pupier; Laure Guenee; Alexandre Alexakis; Chem.Commun. 50 (2014) 13461–; doi:10.1039/C4cc05923A

data_7115879
_publ_section_title
;
 Enantioselective halogenative semi-pinacol rearrangement: a
 stereodivergent reaction on a racemic mixture
;
_journal_name_full               Chem.Commun.
_journal_page_first              13461
_journal_paper_doi               10.1039/C4cc05923A
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 F O2'
_chemical_formula_sum            'C16 H19 F O2'
_chemical_formula_weight         262.31
_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            4
_cell_length_a                   6.10937(8)
_cell_length_b                   10.50654(13)
_cell_length_c                   21.0764(3)
_cell_measurement_reflns_used    4243
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.5560
_cell_measurement_theta_min      4.1350
_cell_volume                     1352.86(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_acta
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6288
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         72.70
_diffrn_reflns_theta_min         4.20
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2832
_exptl_crystal_size_mid          0.1300
_exptl_crystal_size_min          0.0760
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.10(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                2501
_reflns_number_total             2622
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05923a2.cif
_cod_data_source_block           FR1221
_cod_database_code               7115879