A base-promoted tandem approach to bicyclic 8-membered ring ketones.
Dos Santos, Emerson E. F.; de Souza, Gabriela F. P.; Simoni, Deborah A.; Salles, Jr, Airton G; Organic & biomolecular chemistry 18 (2020) 3249–3253; doi:10.1039/d0ob00618a

data_7157464
_publ_section_title
;
 A base-promoted tandem approach to bicyclic 8-membered ring ketones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3249
_journal_page_last               3253
_journal_paper_doi               10.1039/d0ob00618a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_chemical_name_systematic
(4Z)-2,4-diphenyl-8,9-dihydrocycloocta[b]furan-6(7H)-one
_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_block_doi                 10.5517/ccdc.csd.cc21hcpm
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-01-17 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.281(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6541(5)
_cell_length_b                   5.7809(3)
_cell_length_c                   33.543(2)
_cell_measurement_reflns_used    92
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.79
_cell_measurement_theta_min      9.28
_cell_volume                     1664.57(16)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2010)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2010)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.854
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            6055
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.820
_diffrn_reflns_theta_min         5.152
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone and water'
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0584
_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^)+1.1175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2018
_reflns_number_total             2583
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {d9bb4aa3-109e-40ba-bc30-91ae974a3651}
_cod_data_source_file            d0ob00618a2.cif
_cod_data_source_block           FUR-A
_cod_depositor_comments          'Adding full bibliography for 7157464.cif.'
_cod_original_cell_volume        1664.55(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157464
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2014-3
_shelx_res_checksum              67838