Brønsted acid-catalyzed synthesis of spirocyclobutanes <i>via</i> heteroannulation of vinyloxyphenylbicyclobutanes with water.
Takatsuki, Masaharu; Aoyama, Hiroshi; Arisawa, Mitsuhiro; Sako, Makoto; Organic & biomolecular chemistry 22 (2024) 4727–4731; doi:10.1039/d4ob00451e

data_7159951
_publ_section_title
;
 Br&#xf8;nsted acid-catalyzed synthesis of spirocyclobutanes <i>via</i>
 heteroannulation of vinyloxyphenylbicyclobutanes with water.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4727
_journal_page_last               4731
_journal_paper_doi               10.1039/d4ob00451e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H20 O3 S Si'
_chemical_formula_sum            'C18 H20 O3 S Si'
_chemical_formula_weight         344.50
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-01-09 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.719(6)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.1061(7)
_cell_length_b                   8.2101(4)
_cell_length_c                   16.7736(9)
_cell_measurement_reflns_used    9544
_cell_measurement_temperature    143
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.37
_cell_volume                     1804.74(16)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      143
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12077
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         4.255
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0495P)^2^+1.1650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1295
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2831
_reflns_number_total             3259
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d4ob00451e2.cif
_cod_data_source_block           4
_cod_depositor_comments          'Adding full bibliography for 7159951.cif.'
_cod_original_cell_volume        1804.73(16)
_cod_database_code               7159951
_shelx_res_checksum              60111