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_4514912
_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_absolute_configuration rm
_chemical_formula_sum            'C25 H27 N3 O6'
_chemical_formula_weight         465.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4995(11)
_cell_length_b                   18.143(4)
_cell_length_c                   22.295(5)
_cell_measurement_reflns_used    4885
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.3173
_cell_measurement_theta_min      3.9655
_cell_volume                     2224.5(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_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 0.973
_diffrn_measured_fraction_theta_max 0.992
_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  0.0708
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14400
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.718
_diffrn_reflns_theta_min         3.965
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Flack x determined using 1354 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0560
_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^)+(0.1094P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1595
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3552
_reflns_number_total             3915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00005_si_005.cif
_cod_data_source_block           cu_170540lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'RM' changed to 'rm'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_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_original_cell_volume        2224.6(8)
_cod_database_code               4514912
_shelxl_version_number           2014/6
_shelx_res_checksum              20218
_shelx_hkl_checksum              23375