Direct enantioseparation of 1-(2-hydroxyphenyl) ethylamines via diastereomeric salt formation: chiral recognition mechanism based on the crystal structure
Kodama, Koichi; Hayashi, Naoki; Fujita, Mikidai; Hirose, Takuji; RSC Advances 4 (2014) 25609–; doi:10.1039/c4ra00414k

data_7235476
_publ_section_title
;
 Direct enantioseparation of 1-(2-hydroxyphenyl) ethylamines via
 diastereomeric salt formation: chiral recognition mechanism based on the
 crystal structure
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              25609
_journal_paper_doi               10.1039/c4ra00414k
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C16 H27 N O'
_chemical_formula_weight         249.39
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 105.9770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4268(18)
_cell_length_b                   9.5663(11)
_cell_length_c                   11.1965(13)
_cell_measurement_temperature    150(2)
_cell_volume                     1588.5(3)
_computing_cell_refinement       'APEX II (Bruker, 2005)'
_computing_data_collection       'APEX II (Bruker, 2005)'
_computing_molecular_graphics    'Mercury Version 3.1'
_computing_publication_material  'Mercury Version 3.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_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  0.1447
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7388
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9689
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0925P)^2^+0.5908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2147
_reflns_number_gt                2366
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra00414k2.cif
_cod_data_source_block           (RS)-1b
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7235476