Triflic Anhydride Mediated Cyclization of 5-Hydroxy-Substituted Pyrrolidinones for the Preparation of α-Trifluoromethylsulfonamido Furans
Albert Padwa; Paitoon Rashatasakhon; Mickea Rose; Journal of Organic Chemistry 68 (2003) 5139–5146; doi:10.1021/jo0341970

data_4022418
_publ_section_title
;
 Triflic Anhydride Mediated Cyclization of 5-Hydroxy-Substituted
 Pyrrolidinones for the Preparation of
 \a-Trifluoromethylsulfonamido Furans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5139
_journal_page_last               5146
_journal_paper_doi               10.1021/jo0341970
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C9 H10 F3 N O5 S'
_chemical_formula_weight         301.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.649(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4252(4)
_cell_length_b                   5.7427(2)
_cell_length_c                   19.6190(6)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.641
_cell_measurement_theta_min      3.966
_cell_volume                     1255.99(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        65.99
_diffrn_reflns_theta_max         65.99
_diffrn_reflns_theta_min         3.97
_exptl_absorpt_coefficient_mu    2.858
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.72861
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platlet
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0021(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1967
_reflns_number_gt                1807
_reflns_number_total             1955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0341970si20030218_024847.cif
_cod_data_source_block           pr126s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022418