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_7159933
_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         'C25 H21 N4 O3, C H4 O'
_chemical_formula_sum            'C26 H25 N4 O4'
_chemical_formula_weight         457.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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
;
2022-11-11 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6494(3)
_cell_length_b                   10.3451(3)
_cell_length_c                   21.0786(6)
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.20
_cell_volume                     2296.88(11)
_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      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29945
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.954
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8821.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0512P)^2^+1.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4573
_reflns_number_total             6100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00353e2.cif
_cod_data_source_block           mv1110
_cod_depositor_comments
'Adding full bibliography for 7159930--7159933.cif.'
_cod_database_code               7159933
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S' \\sim O1S-C1S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) = Uanis(C1S')
4. Others
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=1-FVAR(1)
 Sof(C1S')=Sof(H1SD)=Sof(H1SE)=Sof(H1SF)=FVAR(1)
5.a Riding coordinates:
 N3(H3), O1S(H1S)
5.b Ternary CH refined with riding coordinates:
 C19(H19)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C6(H6), C2(H2), C11(H11), C5(H5), C1(H1), C15(H15),
 C3(H3A), C13(H13)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C1S(H1SA,H1SB,
 H1SC), C1S'(H1SD,H1SE,H1SF)
;
_shelx_res_checksum              90879
_olex2_submission_special_instructions 'No special instructions were received'