Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates.
Badmus, Fatimat O.; Malone, Joshua A.; Fronczek, Frank R.; Kartika, Rendy; Chemical communications (Cambridge, England) 56 (2020) 5034–5037; doi:10.1039/d0cc01796e

data_1557667
_publ_section_title
;
 Synthesis of functionalized tetrahydropyrans via cascade cycloaddition
 involving silyloxyallyl cation intermediates.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5034
_journal_page_last               5037
_journal_paper_doi               10.1039/d0cc01796e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C21 H24 O2'
_chemical_formula_sum            'C21 H24 O2'
_chemical_formula_weight         308.40
_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
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-11 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.249(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   9.4167(5)
_cell_length_c                   13.1769(7)
_cell_measurement_reflns_used    3580
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      31.38
_cell_measurement_theta_min      2.66
_cell_volume                     1610.59(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18011
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.535
_diffrn_reflns_theta_min         2.122
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0898P)^2^+0.2215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4009
_reflns_number_total             5371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01796e2.cif
_cod_data_source_block           Badmus1
_cod_depositor_comments          'Adding full bibliography for 1557667.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1557667
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              87618
_shelx_hkl_checksum              25917