Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused Tetrahydroisoquinolines via Pictet-Spengler Reaction.
Liu, Shih-I; Haung, Jia-Yun; Barve, Indrajeet J.; Huang, Sheng-Cih; Sun, Chung-Ming; ACS combinatorial science 21 (2019) 336–344; doi:10.1021/acscombsci.9b00005

data_4514913
_publ_section_title
;
 Enantioselective Synthesis of Hydantoin and Diketopiperazine-Fused
 Tetrahydroisoquinolines via Pictet-Spengler Reaction.
;
_journal_issue                   4
_journal_name_full               'ACS combinatorial science'
_journal_page_first              336
_journal_page_last               344
_journal_paper_doi               10.1021/acscombsci.9b00005
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C23 H23 N2 O4 S'
_chemical_formula_weight         423.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                100.872(3)
_cell_angle_beta                 90.005(4)
_cell_angle_gamma                111.647(4)
_cell_formula_units_Z            8
_cell_length_a                   14.8110(13)
_cell_length_b                   16.4734(14)
_cell_length_c                   19.6150(16)
_cell_measurement_reflns_used    212
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.6020
_cell_measurement_theta_min      7.3324
_cell_volume                     4355.7(7)
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40825
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.781
_diffrn_reflns_theta_min         2.947
_exptl_absorpt_coefficient_mu    1.582
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.7886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.916
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1255
_refine_ls_number_reflns         15085
_refine_ls_number_restraints     516
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0798P)^2^+7.4822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13763
_reflns_number_total             15085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00005_si_004.cif
_cod_data_source_block           cu_170538LT_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514913
_shelxl_version_number           2014/6
_shelx_res_checksum              11572
_shelx_hkl_checksum              37692