Metal/catalyst-free sequential C–N bond forming cascades at room temperature: environment-friendly one-pot synthesis of 5-aminoimidazoles from aryl glyoxals, anilines, and amidines
Jalani, Hitesh B.; Sivaraman, Aneesh; Min, Kyoung ho; Lee, Hwa Young; Oh, Na Kyoung; Kang, Hyeseul; Keum, Gyochang; Choi, Yongseok; Lee, Kyeong; Green Chemistry 24 (2022) 6501–6510; doi:10.1039/D2GC01407F

data_7245192
_publ_section_title
;
 Metal/catalyst-free sequential C--N bond forming cascades at room
 temperature: environment-friendly one-pot synthesis of 5-aminoimidazoles
 from aryl glyoxals, anilines, and amidines
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              6501
_journal_page_last               6510
_journal_paper_doi               10.1039/D2GC01407F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C29 H21 N3 O'
_chemical_formula_sum            'C29 H21 N3 O'
_chemical_formula_weight         427.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-04-12 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                79.178(4)
_cell_angle_beta                 74.762(3)
_cell_angle_gamma                80.249(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3505(10)
_cell_length_b                   10.5661(14)
_cell_length_c                   11.8126(13)
_cell_measurement_reflns_used    8506
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.20
_cell_volume                     1097.1(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10716
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.470
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.200
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.0243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                3834
_reflns_number_total             4945
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d2gc01407f2.cif
_cod_data_source_block           KHM-IV-53A
_cod_depositor_comments          'Adding full bibliography for 7245192.cif.'
_cod_database_code               7245192