Diastereoselective Desymmetrization of Prochiral Cyclopentenediones via Cycloaddition Reaction with N-Phenacylbenzothiazolium Bromides.
Chandra Sahoo, Subas; Joshi, Mayank; Chandra Pan, Subhas; The Journal of organic chemistry 82 (2017) 12763–12770; doi:10.1021/acs.joc.7b01964

data_4033027
_publ_section_title
;
 Diastereoselective Desymmetrization of Prochiral Cyclopentenediones via
 Cycloaddition Reaction with N-Phenacylbenzothiazolium Bromides.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12763
_journal_page_last               12770
_journal_paper_doi               10.1021/acs.joc.7b01964
_journal_volume                  82
_journal_year                    2017
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C28 H23 N O3 S'
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53
_chemical_name_systematic        Unknown
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.985(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4330(10)
_cell_length_b                   8.4143(6)
_cell_length_c                   20.1570(14)
_cell_measurement_reflns_used    10260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.02
_cell_volume                     2278.0(3)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9228
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method 'Toluene and methanol solvent mixture'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.5887P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                2875
_reflns_number_total             3990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01964_si_002.cif
_cod_data_source_block           scs-p10-77-2a
_cod_depositor_comments
'Adding full bibliography for 4033027--4033028.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4033027