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_4518843
_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_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C18 H16 O4 Se'
_chemical_formula_sum            'C18 H16 O4 Se'
_chemical_formula_weight         375.28
_chemical_name_common            2b
_chemical_name_systematic
'(3R,4R/3S,4S)-Tetrahydroselenophene-3,4-diyl dibenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-11-24 deposited with the CCDC.	2021-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.52(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   11.390(3)
_cell_length_b                   5.9749(19)
_cell_length_c                   12.292(3)
_cell_measurement_reflns_used    1316
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      3.62
_cell_volume                     797.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1253
_diffrn_reflns_av_unetI/netI     0.1781
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6413
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_min         3.417
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.34
_refine_diff_density_min         -1.36
_refine_ls_abs_structure_details
;
 Flack x determined using 395 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.1348
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1767P)^2^+13.2888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3477
_refine_ls_wR_factor_ref         0.3988
_reflns_Friedel_coverage         0.585
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.614
_reflns_number_gt                1867
_reflns_number_total             2987
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            2046025.cif
_cod_data_source_block           xcalibur
_cod_database_code               4518843
_shelx_res_checksum              45012
_shelx_hkl_checksum              58600