A new hydrogen-bonding motif for chiral recognition in the diastereomeric salts of racemic 1-phenylethylamine derivatives with enantiopure O-ethyl phenylphosphonothioic acid.
Kobayashi, Yuka; Morisawa, Fumi; Saigo, Kazuhiko; Organic letters 6 (2004) 4227–4230; doi:10.1021/ol0483145

data_1506972
_publ_section_title
;
 A new hydrogen-bonding motif for chiral recognition in the diastereomeric
 salts of racemic 1-phenylethylamine derivatives with enantiopure O-ethyl
 phenylphosphonothioic acid.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4227
_journal_page_last               4230
_journal_paper_doi               10.1021/ol0483145
_journal_volume                  6
_journal_year                    2004
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H21 Br N O2 P S '
_chemical_formula_sum            'C16 H21 Br N O2 P S'
_chemical_formula_weight         402.29
_chemical_name_systematic
;
(R)-1-(p-bromophenyl)ethylammonium_(Sp)-O-ethyl phenylphosphonothioate
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   13.8231(8)
_cell_length_b                   13.8231(8)
_cell_length_c                   39.921(3)
_cell_measurement_reflns_used    13480
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     7628.0(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.088
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            49817
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3502.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.90
_refine_diff_density_min         -1.49
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     439
_refine_ls_number_reflns         37396
_refine_ls_R_factor_gt           0.1041
_refine_ls_shift/su_max          0.1299
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1137
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_reflns_threshold_expression     F^2^>2.0\s(F^2^)
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_cod_data_source_block           '__1_2h'
_cod_original_formula_sum        'C16 H21 Br N O2 P S '
_cod_database_code               1506972