Kinetic Resolution of Racemic Alcohols Using Thioamide Modified 1-Methyl-histidine Methyl Ester
Xue-Li Geng; Jia Wang; Guo-Xing Li; Peng Chen; Shu-Fang Tian; Jin Qu; Journal of Organic Chemistry 73 (2008) 8558–8562; doi:10.1021/jo801859m

data_4023831
_publ_section_title
;
 Kinetic Resolution of Racemic Alcohols Using
 Thioamide Modified 1-Methyl-histidine Methyl Ester
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8558
_journal_page_last               8562
_journal_paper_doi               10.1021/jo801859m
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H13 N3 O5 S'
_chemical_formula_sum            'C24 H33 Cl4 N3 O2 S'
_chemical_formula_weight         569.39
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 93.528(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.551(10)
_cell_length_b                   8.405(3)
_cell_length_c                   15.485(7)
_cell_measurement_reflns_used    3355
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.8
_cell_volume                     2929(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15111
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     256
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0791
_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^)+(0.1281P)^2^+1.0791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.2272
_reflns_number_gt                3733
_reflns_number_total             5089
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801859m_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4023831