Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a Selenonium Intermediate
Iwaoka, Michio; Hiyoshi, Yuta; Arai, Shota; Ito, Takeru; ACS Omega  (2021) –; doi:10.1021/acsomega.1c02160

data_4518845
_publ_section_title
;
 Synthesis of 4-Selenothreofuranose Derivatives via Pummerer-Type
 Reactions of trans-3,4-Dioxygenated Tetrahydroselenophenes Mediated by a
 Selenonium Intermediate
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c02160
_journal_year                    2021
_chemical_formula_moiety         'C21 H35 Cl N4 O3 Se Si2'
_chemical_formula_sum            'C21 H35 Cl N4 O3 Se Si2'
_chemical_formula_weight         562.12
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-02-08 deposited with the CCDC.	2021-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.018(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   18.7678(5)
_cell_length_b                   9.5170(2)
_cell_length_c                   15.5255(5)
_cell_measurement_reflns_used    12609
_cell_measurement_temperature    103
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.57
_cell_volume                     2605.52(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      103
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.432
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168.00
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0312P)^2^+2.2713P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5676
_reflns_number_total             6916
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            2061703.cif
_cod_data_source_block           xcalibur
_cod_database_code               4518845
_shelx_res_checksum              70649
_shelx_hkl_checksum              57112