Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans <i>via</i> palladium-catalyzed cascade cyclization of alkenyl ethers.
Zhou, Fei; Li, Can; Li, Meng; Jin, Yangbin; Jiang, Huanfeng; Zhang, Yingjun; Wu, Wanqing; Chemical communications (Cambridge, England) 57 (2021) 4799–4802; doi:10.1039/d1cc00709b

data_7128121
_publ_section_title
;
 Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans <i>via</i>
 palladium-catalyzed cascade cyclization of alkenyl ethers.
;
_journal_issue                   39
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4799
_journal_page_last               4802
_journal_paper_doi               10.1039/d1cc00709b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H16 F N O2'
_chemical_formula_sum            'C23 H16 F N O2'
_chemical_formula_weight         357.37
_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             2019-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-30 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                72.075(2)
_cell_angle_beta                 83.916(2)
_cell_angle_gamma                83.801(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7119(3)
_cell_length_b                   11.2727(7)
_cell_length_c                   14.3335(8)
_cell_measurement_reflns_used    2922
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.918
_cell_measurement_theta_min      2.754
_cell_volume                     870.39(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9745
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.754
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0890 before and 0.0461 after correction. The Ratio of minimum to maximum transmission is 0.9378. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0394P)^2^+0.3574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2457
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00709b2.cif
_cod_data_source_block           1104zf1_0m
_cod_depositor_comments
'Adding full bibliography for 7128121--7128122.cif.'
_cod_database_code               7128121
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F2(0.8) H6(0.75) H13(0.25) F1(0.2)
3.a Ternary CH refined with riding coordinates:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C15(H15), C2(H2), C23(H23), C11(H11), C1(H1), C5(H5), C6(H6),
 C12(H12), C20(H20), C13(H13), C14(H14), C22(H22), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'