Imidazole-catalyzed construction of bridged bicyclo [3.3.1] ketals <i>via</i> formal [3 + 3]-cycloaddition of naphthols and 2-hydroxyl chromene derivatives.
Budakoti, Asha; Jha, Priyankar; Verma, Meenakshi; Vasudev, Prema G.; Gupta, Atul; Organic & biomolecular chemistry 23 (2025) 2793–2796; doi:10.1039/d4ob02068e

data_7160369
_publ_section_title
;
 Imidazole-catalyzed construction of bridged bicyclo [3.3.1] ketals
 <i>via</i> formal [3 + 3]-cycloaddition of naphthols and 2-hydroxyl
 chromene derivatives.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2793
_journal_page_last               2796
_journal_paper_doi               10.1039/d4ob02068e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-07-30 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.555(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9042(17)
_cell_length_b                   10.4909(11)
_cell_length_c                   10.2599(11)
_cell_measurement_reflns_used    42348
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      72.117
_cell_measurement_theta_min      7.093
_cell_volume                     1677.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            42348
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.117
_diffrn_reflns_theta_min         7.093
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.671
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0896P)^2^+0.5251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3052
_reflns_number_total             3133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02068e2.cif
_cod_data_source_block           S1
_cod_depositor_comments
'Adding full bibliography for 7160369--7160370.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160369
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              56270