Cu(ii)-catalyzed annulation of α,β-unsaturated ketoxime acetates with 3-formylchromones for the synthesis of functionalized 2,4-diarylpyridines
Yang, Jing; Hu, Xing-Mei; Zhao, Ke-Hua; Huang, Kun; Yan, Sheng-Jiao; New Journal of Chemistry 48 (2024) 11682–11687; doi:10.1039/D4NJ01648C

data_7063256
_publ_section_title
;
 Cu(ii)-catalyzed annulation of \a,\b-unsaturated ketoxime acetates with
 3-formylchromones for the synthesis of functionalized 2,4-diarylpyridines
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11682
_journal_page_last               11687
_journal_paper_doi               10.1039/D4NJ01648C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H15 Br2 N3 O2 S'
_chemical_formula_sum            'C20 H15 Br2 N3 O2 S'
_chemical_formula_weight         521.23
_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
_audit_creation_date             2023-05-05
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-12-24 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                97.903(2)
_cell_angle_beta                 99.085(2)
_cell_angle_gamma                99.491(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8970(5)
_cell_length_b                   10.6539(6)
_cell_length_c                   14.6586(8)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.23
_cell_volume                     1184.09(12)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34239
_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         28.366
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1217 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.7685.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.6548P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4998
_reflns_number_total             5933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01648c2.cif
_cod_data_source_block           1_sq
_cod_depositor_comments          'Adding full bibliography for 7063256.cif.'
_cod_database_code               7063256
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C5(H5), C6(H6), C16(H16), C17(H17), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.438
_shelx_estimated_absorpt_t_max   0.539
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              91735
_shelx_fab_checksum              872