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_7063331
_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         'C27 H22 Br N O2'
_chemical_formula_sum            'C27 H22 Br N O2'
_chemical_formula_weight         472.36
_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     dual
_audit_creation_date             2022-08-10
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-06-28 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                110.335(2)
_cell_angle_beta                 99.439(2)
_cell_angle_gamma                92.472(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2238(5)
_cell_length_b                   10.8056(5)
_cell_length_c                   12.0232(7)
_cell_measurement_reflns_used    4700
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.25
_cell_volume                     1101.93(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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      150.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0604
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.022
_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    1.889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1614 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.8800.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+0.4218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3750
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01648c2.cif
_cod_data_source_block           1
_cod_database_code               7063331
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.681
_shelx_estimated_absorpt_t_max   0.805
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              34737