Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis.
Wang, Lei; Rahman, Abdul; Lin, Xufeng; Organic & biomolecular chemistry  (2017) –; doi:10.1039/c7ob01149k

data_7155757
_publ_section_title
;
 Enantioselective synthesis of cyclic quaternary \a-amino acid derivatives
 by chiral phosphoric acid catalysis.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/c7ob01149k
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H14 N2 O4 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C17.5 H15 Cl N2 O4 S'
_chemical_formula_weight         384.82
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-04-28 deposited with the CCDC.
2017-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                103.879(2)
_cell_angle_beta                 107.903(2)
_cell_angle_gamma                97.3020(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2173(5)
_cell_length_b                   10.0044(6)
_cell_length_c                   11.8002(7)
_cell_measurement_reflns_used    6071
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.04
_cell_volume                     874.73(9)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7540
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.9308
_exptl_absorpt_correction_T_min  0.8833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       0.040(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5676
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0246P)^2^+1.2187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                4039
_reflns_number_total             5676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01149k2.cif
_cod_data_source_block           wl-1017
_cod_depositor_comments
;

2017-11-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C17 H14 N2 O4 S), C H2 Cl2'
_cod_original_formula_sum        'C35 H30 Cl2 N4 O8 S2'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     769.65
_cod_database_code               7155757