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_7062802
_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_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 89.824(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4864(11)
_cell_length_b                   10.0490(9)
_cell_length_c                   15.2051(13)
_cell_measurement_reflns_used    8548
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.43
_cell_volume                     1602.3(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28657
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_min         2.429
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             664
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0557P)^2^+0.6585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2476
_reflns_number_total             3966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03766e2.cif
_cod_data_source_block           SA_167_070323_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062800--7062802.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7062802
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              2416