(Dimethylamino)methylene hydantoins as building blocks in the synthesis of oxoaplysinopsins and parabanic acids with antifungal activity.
Barrera, Edson; Jerezano, Alberto V.; Reyes-González, Ulises F; Martínez-López, Daniela; Escalante, Carlos H.; López, Julio; Martínez-Mora, Eder I; Gómez-García, Omar; Andrade-Pavón, Dulce; Villa-Tanaca, Lourdes; Delgado, Francisco; Tamariz, Joaquín; Organic & biomolecular chemistry 22 (2024) 8144–8151; doi:10.1039/d4ob01242a

data_7160139
_publ_section_title
;
 (Dimethylamino)methylene hydantoins as building blocks in the synthesis
 of oxoaplysinopsins and parabanic acids with antifungal activity.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8144
_journal_page_last               8151
_journal_paper_doi               10.1039/d4ob01242a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_compound_source        'Synthesis as described'
_chemical_formula_analytical     'C26 H20 Cl N3 O2'
_chemical_formula_iupac          'C26 H20 N3 O2 Cl'
_chemical_formula_moiety         'C26 H20 N3 O2 Cl'
_chemical_formula_structural     'C26 H20 N3 O2 Cl'
_chemical_formula_sum            'C26 H20 Cl N3 O2'
_chemical_formula_weight         441.9
_chemical_melting_point          487.15
_chemical_name_common            oxo-aplisinopsyn
_chemical_name_systematic
(S,E)-5-((1H-indol-3-yl)methylene)-3-(4-chlorophenyl)-1-(1-phenylethyl)imidazoli
_chemical_properties_physical    Air-sensitive
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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     dual
_atom_sites_solution_secondary   dual
_audit_creation_date             2024-07-18T13:33:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-07-18 deposited with the CCDC.	2024-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5034(4)
_cell_length_b                   18.5739(13)
_cell_length_c                   18.5540(10)
_cell_measurement_reflns_used    2088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      3.31
_cell_measurement_wavelength     0.71073
_cell_volume                     2241.2(2)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies  Version 1.171.36.28'
_computing_data_collection
'CrysAlisPro, Agilent Technologies  Version 1.171.36.28'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies  Version 1.171.36.28'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.2257
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Sapphire 3 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0235664000
_diffrn_orient_matrix_UB_12      0.0260630000
_diffrn_orient_matrix_UB_13      0.0267583000
_diffrn_orient_matrix_UB_21      -0.0143694000
_diffrn_orient_matrix_UB_22      0.0278894000
_diffrn_orient_matrix_UB_23      -0.0255898000
_diffrn_orient_matrix_UB_31      -0.1054609000
_diffrn_orient_matrix_UB_32      0.0019793000
_diffrn_orient_matrix_UB_33      0.0094507000
_diffrn_radiation_monochromator  grafphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13817
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.506
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        >2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     290
_refine_ls_number_reflns         7033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.1943
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                3424
_reflns_number_total             7033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01242a2.cif
_cod_data_source_block           0142-jt
_cod_depositor_comments          'Adding full bibliography for 7160139.cif.'
_cod_database_code               7160139
_shelx_shelxl_version_number     2018/3