Palladium-catalyzed tandem cyclization reaction: access to isoxazoline-benzofuran bis-heterocycles.
Wu, Qing; Han, Yingna; Tang, Tian; Zhang, Shuwei; Yu, Xiuzhao; Zhao, Guofeng; Hu, Weiming; Wang, Lei; Chemical communications (Cambridge, England) 61 (2025) 12928–12931; doi:10.1039/d5cc02682b

data_7134873
_publ_section_title
;
 Palladium-catalyzed tandem cyclization reaction: access to
 isoxazoline-benzofuran bis-heterocycles.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12928
_journal_page_last               12931
_journal_paper_doi               10.1039/d5cc02682b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-07-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-08 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.037(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3859(7)
_cell_length_b                   8.7208(3)
_cell_length_c                   11.3513(4)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.128
_cell_measurement_theta_min      5.635
_cell_volume                     1786.40(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13878
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         5.634
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0976P)^2^+0.3415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2410
_reflns_number_total             3139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02682b2.cif
_cod_data_source_block           20240725_lyl_0m_pl
_cod_depositor_comments          'Adding full bibliography for 7134873.cif.'
_cod_database_code               7134873
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C1(H1), C6(H6), C17(H17), C2(H2), C4(H4), C3(H3), C20(H20),
 C23(H23), C22(H22), C21(H21)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              73381
_shelx_hkl_checksum              13604
_olex2_submission_special_instructions 'No special instructions were received'