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_7160370
_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            'C22 H18 O3'
_chemical_formula_weight         330.36
_space_group_crystal_system      monoclinic
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_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-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                 110.0090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   18.4579(5)
_cell_length_c                   9.9846(3)
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_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      67.778
_cell_measurement_theta_min      5.289
_cell_volume                     1667.61(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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  0.0581
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            43033
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.778
_diffrn_reflns_theta_min         5.289
_diffrn_source                   'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.696
_exptl_crystal_colour            \,Colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0940P)^2^+0.4662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2653
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02068e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7160369--7160370.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7160370
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              95722