Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications
Maeno, Mayaka; Tokunaga, Etsuko; Yamamoto, Takeshi; Suzuki, Toshiya; Ogino, Yoshiyuki; Ito, Emi; Shiro, Motoo; Asahi, Toru; Shibata, Norio; Chem. Sci. 6 (2015) 1043–; doi:10.1039/C4SC03047H

data_1518146
_publ_section_title
;
 Self-disproportionation of enantiomers of thalidomide and its fluorinated
 analogue via gravity-driven achiral chromatography: mechanistic rationale
 and implications
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1043
_journal_paper_doi               10.1039/C4SC03047H
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C13 H9 F N2 O4'
_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_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                 101.237(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.1322(4)
_cell_length_b                   5.2282(3)
_cell_length_c                   15.7662(9)
_cell_measurement_reflns_used    6886
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.15
_cell_measurement_theta_min      5.72
_cell_volume                     576.63(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9552
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             284.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.190
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  875 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0045(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2059
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0210P)^2^+0.2075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                1737
_reflns_number_total             2059
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c4sc03047h2.cif
_cod_data_source_block           20110506
_cod_depositor_comments
'Adding full bibliography for 1518142--1518147.cif.'
_cod_database_code               1518146