Diastereoselective Synthesis of CF(3)-Substituted, Epoxide-Fused Heterocycles with β-(Trifluoromethyl)vinylsulfonium Salts.
Fritz, Sven P.; West, Thomas H.; McGarrigle, Eoghan M.; Aggarwal, Varinder K.; Organic letters 14 (2012) 6370–6373; doi:10.1021/ol303200n

data_1508814
_publ_section_title
;
 Diastereoselective Synthesis of CF(3)-Substituted, Epoxide-Fused
 Heterocycles with \b-(Trifluoromethyl)vinylsulfonium Salts.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6370
_journal_page_last               6373
_journal_paper_doi               10.1021/ol303200n
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 F3 N2 O5 S'
_chemical_formula_sum            'C13 H13 F3 N2 O5 S'
_chemical_formula_weight         366.31
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0772(2)
_cell_length_b                   14.0415(5)
_cell_length_c                   20.6933(6)
_cell_measurement_reflns_used    6569
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.45
_cell_volume                     1475.26(9)
_computing_cell_refinement       'Bruker Apex2'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17823
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.2603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0676
_reflns_number_gt                3185
_reflns_number_total             3428
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303200n_si_004.cif
_cod_data_source_block           sv432_f2_0m
_cod_database_code               1508814