A copper-catalyzed tandem cyclization reaction of <i>N</i>-acyl enamines and electron-deficient alkynes: direct synthesis of alkynyl substituted pyridines.
Gao, Ying; Peng, Ju-Yin; Zhang, Yu-Na; Zhao, Xiao-Liang; Zhao, Yu-Long; Organic & biomolecular chemistry 23 (2025) 4441–4445; doi:10.1039/d5ob00390c

data_7160488
_publ_section_title
;
 A copper-catalyzed tandem cyclization reaction of <i>N</i>-acyl enamines
 and electron-deficient alkynes: direct synthesis of alkynyl substituted
 pyridines.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4441
_journal_page_last               4445
_journal_paper_doi               10.1039/d5ob00390c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C21 N2 O4'
_chemical_formula_sum            'C21 N2 O4'
_chemical_formula_weight         344.23
_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_primary     dual
_audit_creation_date             2021-12-03
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;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-03-04 deposited with the CCDC.	2025-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                96.900(10)
_cell_angle_beta                 104.419(11)
_cell_angle_gamma                106.168(10)
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_cell_length_b                   9.7333(19)
_cell_length_c                   12.207(3)
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_cell_volume                     937.2(4)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
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_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      278.4
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5\% \w and 0.5\% \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
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_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15872
_diffrn_reflns_point_group_measured_fraction_full 0.994
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_diffrn_source                   'microfocus sealed X-ray tube'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0916
_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^)+(0.2000P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2639
_refine_ls_wR_factor_ref         0.2858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             3082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00390c2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160488.cif.'
_cod_original_cell_volume        937.2(3)
_cod_database_code               7160488
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.843
_olex2_refinement_description
;
;
_shelx_res_checksum              83802
_olex2_submission_special_instructions 'No special instructions were received'