Palladium-catalysed alleneamination of γ,δ-unsaturated hydrazones with propargylic acetates: access to tetrahydropyridazines bearing allenes
Wu, Shuaijie; Xu, Shiji; He, Yanru; Sun, Jing; Jiang, Wei; Yan, Chao-Guo; Hu, Weiming; Wang, Lei; Chemical Communications 61 (2025) 6647–6650; doi:10.1039/D4CC06716A

data_7134387
_publ_section_title
;
 Palladium-catalysed alleneamination of \g,\d-unsaturated hydrazones with
 propargylic acetates: access to tetrahydropyridazines bearing allenes
;
_journal_issue                   36
_journal_name_full               'Chemical Communications'
_journal_page_first              6647
_journal_page_last               6650
_journal_paper_doi               10.1039/D4CC06716A
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H26 N2 O'
_chemical_formula_sum            'C24 H26 N2 O'
_chemical_formula_weight         358.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-12-11 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1976(4)
_cell_length_b                   23.2687(13)
_cell_length_c                   24.5001(12)
_cell_measurement_reflns_used    6826
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.84
_cell_measurement_theta_min      2.41
_cell_volume                     4103.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            39193
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.414
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1366 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         8048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0429P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4362
_reflns_number_total             8048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06716a2.cif
_cod_data_source_block           XSJ20230411
_cod_depositor_comments          'Adding full bibliography for 7134387.cif.'
_cod_database_code               7134387
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              9552
_shelx_hkl_checksum              85263