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_1518142
_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 H10 N2 O4 '
_chemical_formula_sum            'C13 H10 N2 O4'
_chemical_formula_weight         258.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.762(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.3156(3)
_cell_length_b                   9.9732(4)
_cell_length_c                   14.5740(5)
_cell_measurement_reflns_used    7535
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.4
_cell_volume                     1178.81(8)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku VariMax RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12229
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536.00
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2122
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                1530
_reflns_number_total             2122
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c4sc03047h2.cif
_cod_data_source_block           RS-revised
_cod_depositor_comments
'Adding full bibliography for 1518142--1518147.cif.'
_cod_original_cell_volume        1178.81(7)
_cod_original_formula_sum        'C13 H10 N2 O4 '
_cod_database_code               1518142