Switching of the Diastereomer Deposited during the Crystallization of N-[(S)-1-Phenylethyl]-2'-carbamoyl-1,1'-binaphthalene-2-carboxylic Acid: Investigation of the Mechanism of Dielectrically Controlled Resolution
Yuichi Kitamoto; Kazumi Suzuki; Naoya Morohashi; Kenichi Sakai; Tetsutaro Hattori; Journal of Organic Chemistry 78 (2013) 597–605; doi:10.1021/jo3024285

data_4027867
_publ_section_title
;
 Switching of the Diastereomer Deposited during the Crystallization of
 N-[(S)-1-Phenylethyl]-2'-carbamoyl-1,1'-binaphthalene-2-carboxylic Acid:
 Investigation of the Mechanism of Dielectrically Controlled Resolution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              597
_journal_page_last               605
_journal_paper_doi               10.1021/jo3024285
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C31 H25 Cl2 N O3'
_chemical_formula_weight         530.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7329(12)
_cell_length_b                   13.8113(15)
_cell_length_c                   16.8109(18)
_cell_measurement_reflns_used    6851
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.28
_cell_volume                     2724.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15198
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.831742
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.163
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0878P)^2^+0.8432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1527
_reflns_number_gt                5257
_reflns_number_total             6076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3024285_si_003.cif
_cod_data_source_block           (SaS)dichloromethane
_cod_database_code               4027867