Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole <i>N</i>-oxides, and aldehydes.
Uvarova, Ekaterina S.; Kutasevich, Anton V.; Lipatov, Egor S.; Pytskii, Ivan S.; Raitman, Oleg A.; Selivantev, Yuriy M.; Mityanov, Vitaly S.; Organic & biomolecular chemistry 22 (2024) 4297–4308; doi:10.1039/d4ob00353e

data_7159932
_publ_section_title
;
 Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted
 imidazole <i>N</i>-oxides, and aldehydes.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4297
_journal_page_last               4308
_journal_paper_doi               10.1039/d4ob00353e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H21 N3 O S'
_chemical_formula_sum            'C23 H21 N3 O S'
_chemical_formula_weight         387.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-11-14 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.6100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4764(2)
_cell_length_b                   8.5980(2)
_cell_length_c                   17.6336(3)
_cell_measurement_reflns_used    9265
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.35
_cell_volume                     2008.27(7)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25188
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.561
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.5153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1822 before and 0.0972 after correction.
The Ratio of minimum to maximum transmission is 0.5977.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0447P)^2^+1.0232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4460
_reflns_number_total             5329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00353e2.cif
_cod_data_source_block           mv1140
_cod_depositor_comments
'Adding full bibliography for 7159930--7159933.cif.'
_cod_database_code               7159932
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C1(H1), C12(H12), C8(H8), C3(H3), C11(H11), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              31777
_olex2_submission_special_instructions 'No special instructions were received'