Divergent coupling of <i>ortho</i>-alkynylnaphthols and <i>p</i>-quinone monoketals through a Michael addition/intramolecular annulation cascade to access benzofuryl β-naphthols.
Begum, Fathima; Bhumannagari, Haripriya; Balasubramanian, Sridhar; Nayani, Kiranmai; Chemical communications (Cambridge, England) 61 (2025) 15003–15006; doi:10.1039/d5cc02688a

data_7135053
_publ_section_title
;
 Divergent coupling of <i>ortho</i>-alkynylnaphthols and <i>p</i>-quinone
 monoketals through a Michael addition/intramolecular annulation cascade
 to access benzofuryl &#x3b2;-naphthols.
;
_journal_issue                   77
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15003
_journal_page_last               15006
_journal_paper_doi               10.1039/d5cc02688a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C36 H22 O2'
_chemical_formula_sum            'C36 H22 O2'
_chemical_formula_weight         486.53
_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-2019/3
_audit_update_record
;
2025-07-16 deposited with the CCDC.	2025-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                98.505(5)
_cell_angle_beta                 98.503(5)
_cell_angle_gamma                106.719(5)
_cell_formula_units_Z            4
_cell_length_a                   10.2845(18)
_cell_length_b                   16.121(3)
_cell_length_c                   17.626(3)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.2845
_cell_measurement_theta_min      2.4925
_cell_volume                     2711.5(8)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2019)'
_computing_data_collection       '<i>APEX5</i> (Bruker, 2023)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68067
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7024
_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_colour            colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         13426
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.5720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7510
_reflns_number_total             13426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02688a4.cif
_cod_data_source_block           mo_va379_0m_sq
_cod_database_code               7135053
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              32083
_shelx_fab_checksum              27227