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_7235478
_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_absolute_configuration rm
_chemical_formula_sum            'C21 H34 N2 O4'
_chemical_formula_weight         378.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 116.504(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.749(4)
_cell_length_b                   8.124(2)
_cell_length_c                   17.552(4)
_cell_measurement_temperature    150(2)
_cell_volume                     2137.3(9)
_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-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9937
_diffrn_reflns_point_group_measured_fraction_full 0.699
_diffrn_reflns_point_group_measured_fraction_max 0.717
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.296
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       platelet
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   10.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     588
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0814
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1169P)^2^+2.7790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2435
_reflns_Friedel_coverage         0.340
_reflns_Friedel_fraction_full    0.385
_reflns_Friedel_fraction_max     0.395
_reflns_number_gt                4024
_reflns_number_total             5394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra00414k2.cif
_cod_data_source_block           1b_7
_cod_original_cell_volume        2137.2(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7235478
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
_shelx_res_checksum              2452