Unusual participation of O-propargyl group during the cyclization of 6-hydroxy-2-propargyl ethers of aryl chalcones: one-pot synthesis of 2-acyl-3-styrylbenzofuran and 7-aryldibenzo[b,d]furan-1,7-diols
Samyuktha, Arimalai Dinakararaja; Ethiraj, Kannatt Radhakrishnan; Shanmugam, Ponnusamy; New Journal of Chemistry 47 (2023) 20818–20830; doi:10.1039/D3NJ03766E

data_7062800
_publ_section_title
;
 Unusual participation of O-propargyl group during the cyclization of
 6-hydroxy-2-propargyl ethers of aryl chalcones: one-pot synthesis of
 2-acyl-3-styrylbenzofuran and 7-aryldibenzo[b,d]furan-1,7-diols
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20818
_journal_page_last               20830
_journal_paper_doi               10.1039/D3NJ03766E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C24 H16 O3'
_chemical_formula_sum            'C24 H16 O3'
_chemical_formula_weight         352.37
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-25 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                105.164(2)
_cell_angle_beta                 92.910(2)
_cell_angle_gamma                109.138(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1787(5)
_cell_length_b                   9.1920(5)
_cell_length_c                   11.2622(6)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.38
_cell_volume                     856.66(8)
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38013
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'i-mu-s-microfocus source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0605P)^2^+0.3197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3088
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03766e2.cif
_cod_data_source_block           SA_98RE_250422_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062800--7062802.cif.'
_cod_database_code               7062800
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              36163