Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes.
Nambu, Hisanori; Onuki, Yuta; Aso, Kana; Kanamori, Momoka; Tomohara, Keisuke; Tsuge, Kiyoshi; Yakura, Takayuki; Chemical communications (Cambridge, England) 60 (2024) 4537–4540; doi:10.1039/d3cc06033k

data_7132853
_publ_section_title
;
 Ring expansion of spirocyclopropanes with stabilized sulfonium ylides:
 highly diastereoselective synthesis of cyclobutanes.
;
_journal_issue                   34
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4537
_journal_page_last               4540
_journal_paper_doi               10.1039/d3cc06033k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 O5'
_chemical_formula_sum            'C22 H20 O5'
_chemical_formula_weight         364.40
_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
;
2023-12-05 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.251(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.08906(16)
_cell_length_b                   9.90544(18)
_cell_length_c                   20.1477(4)
_cell_measurement_reflns_used    16450
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      4.39
_cell_volume                     1812.52(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20217
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.174
_diffrn_reflns_theta_min         4.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768.00
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.5553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3096
_reflns_number_total             3298
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3cc06033k2.cif
_cod_data_source_block           2019Mar_sampleC
_cod_depositor_comments          'Adding full bibliography for 7132853.cif.'
_cod_database_code               7132853
_shelx_res_checksum              66190
_shelx_hkl_checksum              38259